# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_JF2923FMI
_database_code_depnum_ccdc_archive 'CCDC 2087127'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UC DAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.6342(6)
_cell_length_b                   21.7612(13)
_cell_length_c                   9.6649(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2026.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      69.56

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.446
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.756
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_T_max  0.8184
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9041
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.063
_diffrn_reflns_theta_max         69.555
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3667
_reflns_number_gt                3659
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.959

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

JF2923 Duo Cu

A colorless plate with approximate orthogonal dimensions 0.106 x 0.446 x
0.547mm3 was placed and optically centered on the Bruker(1) APEXII CCD system
at --183°C(90K).  Indexing of the unit cell used a random set of reflections
collected from three series of 0.5° wide omega-scans, 10 seconds per frame,
and 30 frames per series that were well distributed in reciprocal space. Data
were collected [CuKa] with 0.5° wide scans, variable time per frame dependent
upon detector 2theta angle and varying phi and omega angles such that nearly
all unique reflections were collected at least once.  The crystal to detector
distance was 5.00cm, thus providing a complete sphere of data to
2thetamax=139.07°.

Structural determination and Refinement:

All crystallographic calculations were performed on an Intel Xeon E5-1620v2
at 3.70GHz an eight core processor and 16GB of extended memory. Data
collected were corrected for Lorentz and polarization effects with Saint(1)
and absorption using Blessing?s method and merged based upon mm2 symmetry as
incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was
implemented to determine the probable space group and set up the initial
files. System symmetry, systematic absences and intensity statistics
indicated the non-centrosymmetric orthorhombic space group Pna21 (no. 33).
The structure was determined by direct methods with the non-hydrogen atoms
being located directly for the molecule using the program XT(5).  The
structure was refined with XL(6). The 14161 data collected were merged, based
upon identical indices to 9041, then for least squares refinement to 3667
unique data [R(int)=0.0189]. All non-hydrogen atoms were refined
anisotropically. Hydrogen atoms were idealized initially and then allowed to
refine freely throughout the final refinement stages except for the methyl
carbon, C(19), that had its hydrogen atoms refined with SADI restraints. The
final structure was refined to convergence with R(F)=2.97%, wR(F2)=7.76%,
GOF=1.072 for all 3367 unique reflections [R(F)=2.97, wR(F2)=7.76 for those
3659 data with Fo > 4?(Fo)]. The final difference-Fourier map was featureless
indicating that the structure is both correct and complete. An empirical
correction for extinction was also attempted and found to be 0.0036(5).  The
absolute structure parameters were determined to be: Flack(x)(7), 0.04(10);
Hooft(y)(8), 0.06(7) and the Parsons(z)(6), 0.12(3) indicating that the
structure?s absolute configuration has been determined reliably; these values
would be close to 1.0 if the structure were inverted. The standard
uncertainties are larger than desired due to the heaviest atoms in the
structure being oxygen.



References:

1.	Bruker (2018) APEXIII (Version 2018.3) and (2016) SAINT (Version 8.37a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H.
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector
Absorption Correction? Universität Göttingen: Göttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison,
Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, Universität Göttingen: Göttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. Universität Göttingen: Göttingen,
Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst.,
A39, 876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst. 41, 96-
103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron


Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193)
for the Dual Source X-ray diffractometer.






;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.3909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     382
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4508(2) 0.57920(9) 0.6564(2) 0.0162(4) Uani 1 1 d . . . . .
N1 N 0.31783(17) 0.59590(8) 0.61429(17) 0.0165(4) Uani 1 1 d . . . . .
O1 O 0.49736(16) 0.58905(7) 0.77025(15) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.5194(2) 0.54490(9) 0.5371(2) 0.0153(4) Uani 1 1 d . . . . .
H2 H 0.527(2) 0.5009(12) 0.569(3) 0.018(6) Uiso 1 1 d . . . . .
C3 C 0.4140(2) 0.54760(9) 0.4182(2) 0.0151(4) Uani 1 1 d . . . . .
H3 H 0.393(3) 0.5052(12) 0.384(3) 0.020(6) Uiso 1 1 d . . . . .
C4 C 0.2829(2) 0.57263(9) 0.4837(2) 0.0160(4) Uani 1 1 d . . . . .
O4 O 0.16837(15) 0.57408(7) 0.43377(16) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.6702(2) 0.56557(9) 0.5092(2) 0.0152(4) Uani 1 1 d . . . . .
O5 O 0.69555(15) 0.62682(6) 0.55539(15) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.7057(2) 0.56410(8) 0.3553(2) 0.0147(4) Uani 1 1 d . . . . .
O6 O 0.75783(15) 0.52652(6) 0.58840(16) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.6065(2) 0.57921(8) 0.2557(2) 0.0141(4) Uani 1 1 d . . . . .
C8 C 0.4537(2) 0.58706(9) 0.2898(2) 0.0146(4) Uani 1 1 d . . . . .
H8 H 0.404(3) 0.5692(11) 0.211(3) 0.013(6) Uiso 1 1 d . . . . .
C9 C 0.8435(2) 0.55455(9) 0.3153(2) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.912(3) 0.5415(12) 0.385(3) 0.018(6) Uiso 1 1 d . . . . .
C10 C 0.8835(2) 0.56129(9) 0.1783(2) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.981(3) 0.5543(11) 0.156(3) 0.015(6) Uiso 1 1 d . . . . .
C11 C 0.7861(2) 0.57819(9) 0.0794(2) 0.0191(4) Uani 1 1 d . . . . .
H11 H 0.815(3) 0.5835(12) -0.014(3) 0.021(6) Uiso 1 1 d . . . . .
C12 C 0.6489(2) 0.58686(9) 0.1180(2) 0.0165(4) Uani 1 1 d . . . . .
H12 H 0.579(3) 0.5990(12) 0.051(3) 0.020(6) Uiso 1 1 d . . . . .
C13 C 0.2268(2) 0.63439(9) 0.6927(2) 0.0164(4) Uani 1 1 d . . . . .
C14 C 0.1895(2) 0.69115(10) 0.6373(2) 0.0190(4) Uani 1 1 d . . . . .
H14 H 0.222(3) 0.7031(12) 0.549(3) 0.019(6) Uiso 1 1 d . . . . .
C15 C 0.1034(2) 0.73006(10) 0.7112(2) 0.0195(4) Uani 1 1 d . . . . .
H15 H 0.076(2) 0.7701(12) 0.676(3) 0.018(6) Uiso 1 1 d . . . . .
C16 C 0.0531(2) 0.71342(10) 0.8419(2) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.0926(2) 0.65655(10) 0.8953(2) 0.0185(4) Uani 1 1 d . . . . .
H17 H 0.058(3) 0.6447(12) 0.983(3) 0.022(6) Uiso 1 1 d . . . . .
C18 C 0.1788(2) 0.61695(10) 0.8228(2) 0.0178(4) Uani 1 1 d . . . . .
H18 H 0.199(3) 0.5782(13) 0.864(3) 0.021(7) Uiso 1 1 d . . . . .
C19 C -0.0423(3) 0.75546(11) 0.9198(2) 0.0256(5) Uani 1 1 d D . . . .
H19A H -0.135(3) 0.7513(16) 0.885(3) 0.060(11) Uiso 1 1 d D . . . .
H19B H -0.020(4) 0.7980(12) 0.913(4) 0.090(16) Uiso 1 1 d D . . . .
H19C H -0.046(3) 0.7458(16) 1.016(3) 0.060(11) Uiso 1 1 d D . . . .
C20 C 0.7889(2) 0.62550(11) 0.6718(3) 0.0248(5) Uani 1 1 d . . . . .
H20A H 0.732(3) 0.6298(12) 0.762(3) 0.021(7) Uiso 1 1 d . . . . .
H20B H 0.851(3) 0.6620(13) 0.663(3) 0.022(6) Uiso 1 1 d . . . . .
C21 C 0.8588(2) 0.56360(11) 0.6588(2) 0.0240(5) Uani 1 1 d . . . . .
H21A H 0.946(3) 0.5662(14) 0.602(3) 0.032(8) Uiso 1 1 d . . . . .
H21B H 0.876(3) 0.5446(14) 0.745(3) 0.028(7) Uiso 1 1 d . . . . .
C22 C 0.4082(2) 0.65424(9) 0.2943(2) 0.0150(4) Uani 1 1 d . . . . .
C23 C 0.4771(2) 0.69928(9) 0.3706(2) 0.0176(4) Uani 1 1 d . . . . .
H23 H 0.557(3) 0.6886(12) 0.427(3) 0.023(6) Uiso 1 1 d . . . . .
C24 C 0.4309(2) 0.75998(9) 0.3668(2) 0.0200(4) Uani 1 1 d . . . . .
H24 H 0.480(3) 0.7901(14) 0.425(3) 0.034(8) Uiso 1 1 d . . . . .
C25 C 0.3167(2) 0.77613(10) 0.2886(2) 0.0212(4) Uani 1 1 d . . . . .
H25 H 0.286(3) 0.8187(13) 0.285(3) 0.022(6) Uiso 1 1 d . . . . .
C26 C 0.2469(2) 0.73160(10) 0.2132(2) 0.0217(4) Uani 1 1 d . . . . .
H26 H 0.171(3) 0.7416(12) 0.157(3) 0.020(6) Uiso 1 1 d . . . . .
C27 C 0.2927(2) 0.67108(10) 0.2162(2) 0.0189(4) Uani 1 1 d . . . . .
H27 H 0.239(3) 0.6396(12) 0.160(3) 0.016(6) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.208(3) . ?
C1 N1 1.392(3) . ?
C1 C2 1.524(3) . ?
N1 C4 1.401(3) . ?
N1 C13 1.429(3) . ?
C2 C3 1.534(3) . ?
C2 C5 1.545(3) . ?
C2 H2 1.01(3) . ?
C3 C4 1.515(3) . ?
C3 C8 1.557(3) . ?
C3 H3 1.00(3) . ?
C4 O4 1.204(3) . ?
C5 O6 1.421(2) . ?
C5 O5 1.427(2) . ?
C5 C6 1.527(3) . ?
O5 C20 1.440(3) . ?
C6 C7 1.395(3) . ?
C6 C9 1.398(3) . ?
O6 C21 1.436(3) . ?
C7 C12 1.402(3) . ?
C7 C8 1.518(3) . ?
C8 C22 1.527(3) . ?
C8 H8 0.98(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.98(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.97(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.95(3) . ?
C12 H12 0.97(3) . ?
C13 C18 1.393(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.95(3) . ?
C15 C16 1.400(3) . ?
C15 H15 0.97(3) . ?
C16 C17 1.394(3) . ?
C16 C19 1.500(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.95(3) . ?
C18 H18 0.95(3) . ?
C19 H19A 0.96(2) . ?
C19 H19B 0.95(2) . ?
C19 H19C 0.95(2) . ?
C20 C21 1.511(3) . ?
C20 H20A 1.03(3) . ?
C20 H20B 1.00(3) . ?
C21 H21A 1.00(3) . ?
C21 H21B 0.95(3) . ?
C22 C27 1.394(3) . ?
C22 C23 1.394(3) . ?
C23 C24 1.394(3) . ?
C23 H23 0.98(3) . ?
C24 C25 1.381(3) . ?
C24 H24 0.98(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.97(3) . ?
C26 C27 1.389(3) . ?
C26 H26 0.94(3) . ?
C27 H27 1.01(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 124.2(2) . . ?
O1 C1 C2 127.94(19) . . ?
N1 C1 C2 107.82(17) . . ?
C1 N1 C4 112.95(17) . . ?
C1 N1 C13 124.22(17) . . ?
C4 N1 C13 122.80(16) . . ?
C1 C2 C3 105.12(16) . . ?
C1 C2 C5 113.43(17) . . ?
C3 C2 C5 118.71(17) . . ?
C1 C2 H2 105.4(15) . . ?
C3 C2 H2 108.2(14) . . ?
C5 C2 H2 105.2(14) . . ?
C4 C3 C2 104.65(16) . . ?
C4 C3 C8 109.86(16) . . ?
C2 C3 C8 117.09(16) . . ?
C4 C3 H3 107.7(15) . . ?
C2 C3 H3 110.2(15) . . ?
C8 C3 H3 107.1(15) . . ?
O4 C4 N1 124.88(19) . . ?
O4 C4 C3 127.30(19) . . ?
N1 C4 C3 107.80(17) . . ?
O6 C5 O5 106.76(15) . . ?
O6 C5 C6 112.31(16) . . ?
O5 C5 C6 106.64(16) . . ?
O6 C5 C2 106.87(16) . . ?
O5 C5 C2 112.20(16) . . ?
C6 C5 C2 112.02(17) . . ?
C5 O5 C20 109.42(15) . . ?
C7 C6 C9 119.68(19) . . ?
C7 C6 C5 120.90(18) . . ?
C9 C6 C5 118.99(18) . . ?
C5 O6 C21 108.76(15) . . ?
C6 C7 C12 118.91(19) . . ?
C6 C7 C8 122.74(18) . . ?
C12 C7 C8 118.35(18) . . ?
C7 C8 C22 113.11(16) . . ?
C7 C8 C3 110.45(16) . . ?
C22 C8 C3 115.79(16) . . ?
C7 C8 H8 105.0(15) . . ?
C22 C8 H8 105.2(14) . . ?
C3 C8 H8 106.4(14) . . ?
C10 C9 C6 120.7(2) . . ?
C10 C9 H9 119.6(16) . . ?
C6 C9 H9 119.6(15) . . ?
C9 C10 C11 119.82(19) . . ?
C9 C10 H10 117.8(16) . . ?
C11 C10 H10 122.4(16) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 121.0(17) . . ?
C10 C11 H11 119.3(17) . . ?
C11 C12 C7 121.1(2) . . ?
C11 C12 H12 121.3(16) . . ?
C7 C12 H12 117.6(16) . . ?
C18 C13 C14 120.16(19) . . ?
C18 C13 N1 121.50(18) . . ?
C14 C13 N1 118.31(18) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 119.7(16) . . ?
C13 C14 H14 120.4(16) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 122.2(16) . . ?
C16 C15 H15 116.8(16) . . ?
C17 C16 C15 117.99(19) . . ?
C17 C16 C19 121.51(19) . . ?
C15 C16 C19 120.5(2) . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17 119.7(16) . . ?
C16 C17 H17 118.4(16) . . ?
C17 C18 C13 119.1(2) . . ?
C17 C18 H18 117.4(17) . . ?
C13 C18 H18 123.4(17) . . ?
C16 C19 H19A 110(2) . . ?
C16 C19 H19B 115(3) . . ?
H19A C19 H19B 106.0(19) . . ?
C16 C19 H19C 112(2) . . ?
H19A C19 H19C 106.5(19) . . ?
H19B C19 H19C 107(2) . . ?
O5 C20 C21 103.39(17) . . ?
O5 C20 H20A 108.9(16) . . ?
C21 C20 H20A 112.8(15) . . ?
O5 C20 H20B 106.9(16) . . ?
C21 C20 H20B 115.9(15) . . ?
H20A C20 H20B 108(2) . . ?
O6 C21 C20 103.79(17) . . ?
O6 C21 H21A 109.8(18) . . ?
C20 C21 H21A 111.6(18) . . ?
O6 C21 H21B 107.0(18) . . ?
C20 C21 H21B 113.4(18) . . ?
H21A C21 H21B 111(3) . . ?
C27 C22 C23 118.78(18) . . ?
C27 C22 C8 117.76(17) . . ?
C23 C22 C8 123.45(18) . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 119.5(16) . . ?
C22 C23 H23 120.5(16) . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 121.7(18) . . ?
C23 C24 H24 117.6(18) . . ?
C24 C25 C26 119.74(19) . . ?
C24 C25 H25 120.3(16) . . ?
C26 C25 H25 120.0(16) . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 121.3(16) . . ?
C27 C26 H26 118.7(16) . . ?
C26 C27 C22 120.9(2) . . ?
C26 C27 H27 117.9(14) . . ?
C22 C27 H27 121.2(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C4 -172.52(18) . . . . ?
C2 C1 N1 C4 4.9(2) . . . . ?
O1 C1 N1 C13 9.4(3) . . . . ?
C2 C1 N1 C13 -173.11(17) . . . . ?
O1 C1 C2 C3 -179.00(19) . . . . ?
N1 C1 C2 C3 3.7(2) . . . . ?
O1 C1 C2 C5 -47.8(3) . . . . ?
N1 C1 C2 C5 134.91(17) . . . . ?
C1 C2 C3 C4 -9.98(19) . . . . ?
C5 C2 C3 C4 -138.11(17) . . . . ?
C1 C2 C3 C8 111.90(18) . . . . ?
C5 C2 C3 C8 -16.2(3) . . . . ?
C1 N1 C4 O4 169.80(19) . . . . ?
C13 N1 C4 O4 -12.1(3) . . . . ?
C1 N1 C4 C3 -11.6(2) . . . . ?
C13 N1 C4 C3 166.45(17) . . . . ?
C2 C3 C4 O4 -168.4(2) . . . . ?
C8 C3 C4 O4 65.1(3) . . . . ?
C2 C3 C4 N1 13.10(19) . . . . ?
C8 C3 C4 N1 -113.39(17) . . . . ?
C1 C2 C5 O6 91.78(19) . . . . ?
C3 C2 C5 O6 -144.07(17) . . . . ?
C1 C2 C5 O5 -24.9(2) . . . . ?
C3 C2 C5 O5 99.2(2) . . . . ?
C1 C2 C5 C6 -144.82(17) . . . . ?
C3 C2 C5 C6 -20.7(2) . . . . ?
O6 C5 O5 C20 -5.3(2) . . . . ?
C6 C5 O5 C20 -125.55(17) . . . . ?
C2 C5 O5 C20 111.46(19) . . . . ?
O6 C5 C6 C7 155.77(17) . . . . ?
O5 C5 C6 C7 -87.6(2) . . . . ?
C2 C5 C6 C7 35.5(2) . . . . ?
O6 C5 C6 C9 -31.8(2) . . . . ?
O5 C5 C6 C9 84.8(2) . . . . ?
C2 C5 C6 C9 -152.07(17) . . . . ?
O5 C5 O6 C21 -13.3(2) . . . . ?
C6 C5 O6 C21 103.19(19) . . . . ?
C2 C5 O6 C21 -133.59(18) . . . . ?
C9 C6 C7 C12 -2.5(3) . . . . ?
C5 C6 C7 C12 169.87(17) . . . . ?
C9 C6 C7 C8 176.78(17) . . . . ?
C5 C6 C7 C8 -10.8(3) . . . . ?
C6 C7 C8 C22 104.3(2) . . . . ?
C12 C7 C8 C22 -76.4(2) . . . . ?
C6 C7 C8 C3 -27.3(2) . . . . ?
C12 C7 C8 C3 151.96(17) . . . . ?
C4 C3 C8 C7 158.79(16) . . . . ?
C2 C3 C8 C7 39.7(2) . . . . ?
C4 C3 C8 C22 28.6(2) . . . . ?
C2 C3 C8 C22 -90.5(2) . . . . ?
C7 C6 C9 C10 1.5(3) . . . . ?
C5 C6 C9 C10 -171.04(18) . . . . ?
C6 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C6 C7 C12 C11 1.6(3) . . . . ?
C8 C7 C12 C11 -177.72(18) . . . . ?
C1 N1 C13 C18 -62.7(3) . . . . ?
C4 N1 C13 C18 119.4(2) . . . . ?
C1 N1 C13 C14 115.6(2) . . . . ?
C4 N1 C13 C14 -62.3(3) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
N1 C13 C14 C15 -178.97(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C14 C15 C16 C19 -178.8(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C19 C16 C17 C18 178.8(2) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
N1 C13 C18 C17 178.90(18) . . . . ?
C5 O5 C20 C21 20.5(2) . . . . ?
C5 O6 C21 C20 25.6(2) . . . . ?
O5 C20 C21 O6 -27.6(2) . . . . ?
C7 C8 C22 C27 128.21(19) . . . . ?
C3 C8 C22 C27 -102.9(2) . . . . ?
C7 C8 C22 C23 -51.0(3) . . . . ?
C3 C8 C22 C23 78.0(2) . . . . ?
C27 C22 C23 C24 -0.6(3) . . . . ?
C8 C22 C23 C24 178.53(19) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C22 0.1(3) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
C8 C22 C27 C26 -178.80(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O1 1.00(3) 2.55(3) 3.408(2) 143(2) 2_664 yes
C20 H20A O1 1.03(3) 2.43(3) 3.070(3) 119(2) . yes

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036


# start Validation Reply Form
_vrf_PLAT089_JF2923FMI           
;
PROBLEM: 089_ALERT_3_B Poor Data / Parameter Ratio (Zmax < 18) .... 5.24 Note
RESPONSE: Data were collected with Cu Kalpha radiation to the maximum 2theta
possible on our diffractometer.  Refining hydrogen atoms freely appears to 
create this issue and yet refining hydrogen atoms should be the method of
choice in my opinion.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2999FMI
_database_code_depnum_ccdc_archive 'CCDC 2087130'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H25 N O4'
_chemical_formula_sum            'C31 H25 N O4'
_chemical_formula_weight         475.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2681(8)
_cell_length_b                   13.4445(10)
_cell_length_c                   18.5225(14)
_cell_angle_alpha                75.214(3)
_cell_angle_beta                 78.879(3)
_cell_angle_gamma                68.820(2)
_cell_volume                     2290.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      68.45

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.732
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8432
_exptl_absorpt_correction_T_max  0.9126
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14547
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         67.903
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.943
_reflns_number_total             7860
_reflns_number_gt                7357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
8 January, 2021
JF2999  MG-4-165 Cu

A pale yellow block with approximate orthogonal dimensions 0.056 x 0.184 x 0.271mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD system at â\/E?183Â°C(90K). Indexing of the unit cell used a random set of reflections collected from three series of 0.5Â° wide omega-scans, 10 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Data were collected [CuKa] with 0.5Â° wide scans, variable time per frame dependent upon detector 2theta angle and varying Ï? and omega angles such that nearly all unique reflections were collected at least once.  The crystal to detector distance was 5.10cm, thus providing a nearly complete sphere of data to 2thetamax=137.22Â°. 

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro5 with Intel i7-7660U at 2.50GHz with two cores, four processors and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint(1) and absorption using Blessingâ\/E?s method and merged as incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the probable space group and set up the initial files. System symmetry, lack of systematic absences and intensity statistics indicated the centrosymmetric triclinic space group P-1 (no. 2). The structure was determined by direct methods with the location of nearly all of the non-hydrogen atoms for the nearly identical two molecules of interest with the program XT(5). The structure was refined with XL(6). The 28411 data collected were merged for identical indices to 14547 reflections and then for least squares refinement to 7860 unique data [R(int)=0.0144]. All full occupancy non-hydrogen atoms were refined anisotropically. Hydrogen atoms were idealized initially and then allowed to refine freely throughout the final refinement. The final structure was refined to convergence with R(F)=3.47%, wR(F2)=8.93%, GOF=1.045 for all 7860 unique reflections [R(F)=3.28, wR(F2)=8.75% for those 7357 data with Fo > 4sigma(Fo)]. The final difference-Fourier map was featureless indicating that the structure is both correct and complete. 

References:

1.	Bruker (2019) APEX3 (Version 2019.1) and (2016) SAINT (Version 8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.
2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-0840444) for the Dual Source X-ray diffractometer.


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.7005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00103(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7860
_refine_ls_number_parameters     850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32190(12) 0.82139(9) 0.32082(7) 0.0182(2) Uani 1 1 d . . . . .
O1 O 0.29601(8) 0.83863(7) 0.24469(5) 0.02051(18) Uani 1 1 d . . . . .
C2 C 0.16300(12) 0.91020(9) 0.22404(7) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.17589(9) 1.01102(7) 0.18430(5) 0.02332(19) Uani 1 1 d . . . . .
C3 C 0.04837(12) 0.92782(9) 0.28884(7) 0.0197(2) Uani 1 1 d . . . . .
O3 O 0.12914(9) 0.86577(7) 0.17207(5) 0.02297(19) Uani 1 1 d . . . . .
C4 C 0.06844(12) 0.86266(9) 0.36047(7) 0.0189(2) Uani 1 1 d . . . . .
C5 C 0.20977(12) 0.77404(9) 0.37131(7) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.2118(14) 0.7147(11) 0.3488(8) 0.017(3) Uiso 1 1 d . . . . .
C6 C 0.47072(12) 0.73541(9) 0.32654(6) 0.0187(2) Uani 1 1 d . . . . .
N6 N 0.54613(10) 0.77335(8) 0.35959(6) 0.0187(2) Uani 1 1 d . . . . .
O6 O 0.51131(9) 0.64886(7) 0.30622(5) 0.0243(2) Uani 1 1 d . . . . .
C7 C 0.47072(12) 0.88059(9) 0.36921(7) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.33794(12) 0.91579(9) 0.34491(7) 0.0186(2) Uani 1 1 d . . . . .
C9 C 0.23898(16) 0.99346(11) 0.11049(8) 0.0311(3) Uani 1 1 d . . . . .
H9A H 0.3483(19) 0.9595(14) 0.1101(9) 0.041(4) Uiso 1 1 d . . . . .
H9B H 0.2171(17) 1.0649(14) 0.0744(10) 0.038(4) Uiso 1 1 d . . . . .
C10 C 0.17546(18) 0.91457(13) 0.09809(8) 0.0360(3) Uani 1 1 d . . . . .
H10A H 0.089(2) 0.9542(16) 0.0673(12) 0.061(6) Uiso 1 1 d . . . . .
H10B H 0.243(2) 0.8599(17) 0.0726(12) 0.058(6) Uiso 1 1 d . . . . .
C11 C -0.07710(13) 1.01273(10) 0.27621(7) 0.0229(3) Uani 1 1 d . . . . .
H11 H -0.0857(15) 1.0588(12) 0.2244(9) 0.028(4) Uiso 1 1 d . . . . .
C12 C -0.18345(13) 1.03348(10) 0.33476(8) 0.0250(3) Uani 1 1 d . . . . .
H12 H -0.2723(16) 1.0923(12) 0.3257(8) 0.028(4) Uiso 1 1 d . . . . .
C13 C -0.16362(13) 0.96949(10) 0.40625(7) 0.0240(3) Uani 1 1 d . . . . .
H13 H -0.2373(15) 0.9840(12) 0.4487(9) 0.026(4) Uiso 1 1 d . . . . .
C14 C -0.03948(13) 0.88410(10) 0.41887(7) 0.0218(3) Uani 1 1 d . . . . .
H14 H -0.0266(15) 0.8386(12) 0.4708(9) 0.025(4) Uiso 1 1 d . . . . .
C15 C 0.24322(12) 0.72424(9) 0.45147(7) 0.0192(2) Uani 1 1 d . . . . .
C16 C 0.22658(12) 0.78617(10) 0.50495(7) 0.0209(2) Uani 1 1 d . . . . .
H16 H 0.1907(15) 0.8650(12) 0.4918(8) 0.024(4) Uiso 1 1 d . . . . .
C17 C 0.26168(13) 0.73533(11) 0.57723(7) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.2477(15) 0.7792(12) 0.6144(9) 0.027(4) Uiso 1 1 d . . . . .
C18 C 0.31645(13) 0.62254(10) 0.59685(7) 0.0244(3) Uani 1 1 d . . . . .
H18 H 0.3438(16) 0.5885(12) 0.6474(9) 0.029(4) Uiso 1 1 d . . . . .
C19 C 0.33415(13) 0.56074(10) 0.54417(7) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.3743(16) 0.4816(13) 0.5576(9) 0.032(4) Uiso 1 1 d . . . . .
C20 C 0.29654(13) 0.61118(10) 0.47239(7) 0.0218(3) Uani 1 1 d . . . . .
H20 H 0.3085(15) 0.5677(12) 0.4336(8) 0.024(4) Uiso 1 1 d . . . . .
C21 C 0.24857(13) 1.02053(9) 0.34921(7) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.1528(16) 1.0480(11) 0.3334(8) 0.023(3) Uiso 1 1 d . . . . .
C22 C 0.29411(14) 1.08767(10) 0.37743(7) 0.0246(3) Uani 1 1 d . . . . .
H22 H 0.2336(16) 1.1601(13) 0.3809(8) 0.028(4) Uiso 1 1 d . . . . .
C23 C 0.42617(14) 1.05040(10) 0.40183(7) 0.0253(3) Uani 1 1 d . . . . .
H23 H 0.4559(16) 1.0978(13) 0.4214(9) 0.030(4) Uiso 1 1 d . . . . .
C24 C 0.51665(13) 0.94513(10) 0.39849(7) 0.0228(3) Uani 1 1 d . . . . .
H24 H 0.6088(16) 0.9164(12) 0.4158(8) 0.027(4) Uiso 1 1 d . . . . .
C25 C 0.69489(12) 0.71983(10) 0.36904(7) 0.0214(3) Uani 1 1 d . . . . .
H25A H 0.7445(15) 0.7682(12) 0.3390(9) 0.026(4) Uiso 1 1 d . . . . .
H25B H 0.7246(15) 0.6551(12) 0.3471(8) 0.023(3) Uiso 1 1 d . . . . .
C26 C 0.72778(12) 0.68839(9) 0.44992(7) 0.0195(2) Uani 1 1 d . . . . .
C27 C 0.62397(13) 0.68946(10) 0.51050(7) 0.0217(3) Uani 1 1 d . . . . .
H27 H 0.5253(16) 0.7115(12) 0.5002(8) 0.028(4) Uiso 1 1 d . . . . .
C28 C 0.65946(13) 0.65719(10) 0.58378(7) 0.0230(3) Uani 1 1 d . . . . .
H28 H 0.5856(16) 0.6588(12) 0.6261(9) 0.029(4) Uiso 1 1 d . . . . .
C29 C 0.79874(13) 0.62316(10) 0.59691(7) 0.0230(3) Uani 1 1 d . . . . .
H29 H 0.8239(15) 0.6000(12) 0.6470(9) 0.026(4) Uiso 1 1 d . . . . .
C30 C 0.90292(13) 0.62173(10) 0.53659(7) 0.0239(3) Uani 1 1 d . . . . .
H30 H 1.0024(17) 0.5980(12) 0.5450(9) 0.032(4) Uiso 1 1 d . . . . .
C31 C 0.86783(13) 0.65444(10) 0.46353(7) 0.0217(3) Uani 1 1 d . . . . .
H31 H 0.9400(16) 0.6537(12) 0.4201(9) 0.026(4) Uiso 1 1 d . . . . .
C41 C -0.05918(12) 0.68804(9) 0.16021(7) 0.0183(2) Uani 1 1 d . . . . .
O41 O -0.15657(8) 0.79083(6) 0.17255(5) 0.02162(19) Uani 1 1 d . . . . .
C42 C -0.27190(12) 0.84163(9) 0.12952(7) 0.0194(2) Uani 1 1 d . . . . .
O42 O -0.24855(9) 0.93081(7) 0.07622(5) 0.0240(2) Uani 1 1 d . . . . .
C43 C -0.30347(12) 0.76809(9) 0.09075(7) 0.0189(2) Uani 1 1 d . . . . .
O43 O -0.38786(9) 0.88609(7) 0.17914(5) 0.0240(2) Uani 1 1 d . . . . .
C44 C -0.24323(11) 0.65494(9) 0.11046(7) 0.0178(2) Uani 1 1 d . . . . .
C45 C -0.14542(12) 0.60990(9) 0.17145(7) 0.0179(2) Uani 1 1 d . . . . .
H45 H -0.2029(14) 0.6189(11) 0.2196(8) 0.019(3) Uiso 1 1 d . . . . .
C46 C 0.03978(12) 0.64693(9) 0.22298(7) 0.0178(2) Uani 1 1 d . . . . .
N46 N 0.17493(10) 0.61540(7) 0.18926(5) 0.0170(2) Uani 1 1 d . . . . .
O46 O 0.00329(9) 0.64066(7) 0.28961(5) 0.0254(2) Uani 1 1 d . . . . .
C47 C 0.17946(12) 0.64323(9) 0.11074(7) 0.0172(2) Uani 1 1 d . . . . .
C48 C 0.04325(12) 0.69012(9) 0.08953(7) 0.0176(2) Uani 1 1 d . . . . .
C49 C -0.27374(16) 1.01180(10) 0.11948(8) 0.0296(3) Uani 1 1 d . . . . .
H49A H -0.2980(16) 1.0841(13) 0.0847(9) 0.031(4) Uiso 1 1 d . . . . .
H49B H -0.1858(18) 0.9974(13) 0.1431(9) 0.039(4) Uiso 1 1 d . . . . .
C50 C -0.39226(17) 0.99395(11) 0.17849(9) 0.0363(3) Uani 1 1 d . . . . .
H50A H -0.377(2) 0.9986(16) 0.2281(12) 0.058(6) Uiso 1 1 d . . . . .
H50B H -0.491(2) 1.0464(16) 0.1625(11) 0.058(5) Uiso 1 1 d . . . . .
C51 C -0.39377(12) 0.81481(10) 0.03490(7) 0.0213(3) Uani 1 1 d . . . . .
H51 H -0.4334(14) 0.8951(12) 0.0220(8) 0.021(3) Uiso 1 1 d . . . . .
C52 C -0.42343(12) 0.74948(10) -0.00226(7) 0.0225(3) Uani 1 1 d . . . . .
H52 H -0.4853(15) 0.7817(11) -0.0427(8) 0.023(3) Uiso 1 1 d . . . . .
C53 C -0.36334(12) 0.63702(10) 0.01672(7) 0.0218(3) Uani 1 1 d . . . . .
H53 H -0.3827(16) 0.5910(12) -0.0104(9) 0.028(4) Uiso 1 1 d . . . . .
C54 C -0.27498(12) 0.59017(10) 0.07302(7) 0.0199(2) Uani 1 1 d . . . . .
H54 H -0.2345(15) 0.5116(12) 0.0863(8) 0.023(4) Uiso 1 1 d . . . . .
C55 C -0.05815(12) 0.49031(9) 0.18036(7) 0.0182(2) Uani 1 1 d . . . . .
C56 C -0.06290(12) 0.42370(10) 0.25129(7) 0.0216(3) Uani 1 1 d . . . . .
H56 H -0.1213(15) 0.4570(12) 0.2930(9) 0.025(4) Uiso 1 1 d . . . . .
C57 C 0.01127(13) 0.31256(10) 0.26260(8) 0.0250(3) Uani 1 1 d . . . . .
H57 H 0.0043(16) 0.2677(13) 0.3121(9) 0.031(4) Uiso 1 1 d . . . . .
C58 C 0.09188(13) 0.26684(10) 0.20284(8) 0.0243(3) Uani 1 1 d . . . . .
H58 H 0.1412(16) 0.1908(13) 0.2108(9) 0.030(4) Uiso 1 1 d . . . . .
C59 C 0.10004(12) 0.33279(10) 0.13209(7) 0.0224(3) Uani 1 1 d . . . . .
H59 H 0.1599(16) 0.3000(12) 0.0898(9) 0.029(4) Uiso 1 1 d . . . . .
C60 C 0.02588(12) 0.44396(9) 0.12052(7) 0.0193(2) Uani 1 1 d . . . . .
H60 H 0.0327(14) 0.4887(11) 0.0701(8) 0.021(3) Uiso 1 1 d . . . . .
C61 C 0.29797(13) 0.62937(10) 0.05920(7) 0.0208(2) Uani 1 1 d . . . . .
H61 H 0.3925(16) 0.5957(12) 0.0755(8) 0.027(4) Uiso 1 1 d . . . . .
C62 C 0.27800(13) 0.66590(10) -0.01673(7) 0.0225(3) Uani 1 1 d . . . . .
H62 H 0.3596(15) 0.6554(11) -0.0538(8) 0.021(3) Uiso 1 1 d . . . . .
C63 C 0.14385(13) 0.71490(10) -0.03911(7) 0.0224(3) Uani 1 1 d . . . . .
H63 H 0.1327(15) 0.7391(12) -0.0917(9) 0.026(4) Uiso 1 1 d . . . . .
C64 C 0.02555(13) 0.72733(9) 0.01409(7) 0.0205(2) Uani 1 1 d . . . . .
H64 H -0.0677(17) 0.7620(12) -0.0027(9) 0.030(4) Uiso 1 1 d . . . . .
C65 C 0.29809(12) 0.57919(9) 0.22945(7) 0.0189(2) Uani 1 1 d . . . . .
H65A H 0.2607(15) 0.5767(11) 0.2834(9) 0.023(4) Uiso 1 1 d . . . . .
H65B H 0.3456(15) 0.6327(11) 0.2135(8) 0.021(3) Uiso 1 1 d . . . . .
C66 C 0.39941(12) 0.46835(9) 0.21869(6) 0.0175(2) Uani 1 1 d . . . . .
C67 C 0.54257(12) 0.44479(10) 0.22101(7) 0.0193(2) Uani 1 1 d . . . . .
H67 H 0.5747(15) 0.5024(12) 0.2263(8) 0.025(4) Uiso 1 1 d . . . . .
C68 C 0.63612(13) 0.34111(10) 0.21641(7) 0.0218(3) Uani 1 1 d . . . . .
H68 H 0.7349(16) 0.3266(12) 0.2188(8) 0.026(4) Uiso 1 1 d . . . . .
C69 C 0.58748(13) 0.26104(10) 0.20883(7) 0.0227(3) Uani 1 1 d . . . . .
H69 H 0.6539(16) 0.1888(13) 0.2044(8) 0.027(4) Uiso 1 1 d . . . . .
C70 C 0.44502(13) 0.28432(10) 0.20585(7) 0.0221(3) Uani 1 1 d . . . . .
H70 H 0.4097(15) 0.2269(12) 0.2010(8) 0.027(4) Uiso 1 1 d . . . . .
C71 C 0.35159(13) 0.38766(10) 0.21054(7) 0.0199(2) Uani 1 1 d . . . . .
H71 H 0.2533(16) 0.4036(11) 0.2096(8) 0.024(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4305(14) . ?
C1 C8 1.5184(16) . ?
C1 C6 1.5512(16) . ?
C1 C5 1.5543(16) . ?
O1 C2 1.4147(14) . ?
C2 O3 1.4060(14) . ?
C2 O2 1.4069(14) . ?
C2 C3 1.5102(17) . ?
O2 C9 1.4343(17) . ?
C3 C11 1.3910(17) . ?
C3 C4 1.3970(17) . ?
O3 C10 1.4317(18) . ?
C4 C14 1.3954(17) . ?
C4 C5 1.5188(16) . ?
C5 C15 1.5145(17) . ?
C5 H5 0.982(14) . ?
C6 O6 1.2174(14) . ?
C6 N6 1.3646(16) . ?
N6 C7 1.4076(15) . ?
N6 C25 1.4582(15) . ?
C7 C24 1.3798(17) . ?
C7 C8 1.3954(16) . ?
C8 C21 1.3880(16) . ?
C9 C10 1.512(2) . ?
C9 H9A 1.047(18) . ?
C9 H9B 0.997(17) . ?
C10 H10A 1.05(2) . ?
C10 H10B 0.96(2) . ?
C11 C12 1.3870(18) . ?
C11 H11 1.001(16) . ?
C12 C13 1.3896(19) . ?
C12 H12 0.978(15) . ?
C13 C14 1.3849(18) . ?
C13 H13 0.985(15) . ?
C14 H14 1.003(15) . ?
C15 C20 1.3929(17) . ?
C15 C16 1.3987(17) . ?
C16 C17 1.3895(18) . ?
C16 H16 0.969(15) . ?
C17 C18 1.3889(18) . ?
C17 H17 0.975(15) . ?
C18 C19 1.3828(19) . ?
C18 H18 0.978(16) . ?
C19 C20 1.3875(18) . ?
C19 H19 0.976(16) . ?
C20 H20 1.000(15) . ?
C21 C22 1.3953(18) . ?
C21 H21 0.992(15) . ?
C22 C23 1.3871(18) . ?
C22 H22 0.958(16) . ?
C23 C24 1.3936(18) . ?
C23 H23 0.965(16) . ?
C24 H24 0.967(15) . ?
C25 C26 1.5183(17) . ?
C25 H25A 0.968(16) . ?
C25 H25B 0.979(15) . ?
C26 C27 1.3898(17) . ?
C26 C31 1.3953(17) . ?
C27 C28 1.3926(18) . ?
C27 H27 0.990(15) . ?
C28 C29 1.3851(18) . ?
C28 H28 0.978(16) . ?
C29 C30 1.3885(19) . ?
C29 H29 0.955(16) . ?
C30 C31 1.3872(18) . ?
C30 H30 0.985(16) . ?
C31 H31 0.982(15) . ?
C41 O41 1.4271(13) . ?
C41 C48 1.5140(16) . ?
C41 C46 1.5529(15) . ?
C41 C45 1.5558(16) . ?
O41 C42 1.4163(14) . ?
C42 O43 1.4014(14) . ?
C42 O42 1.4078(14) . ?
C42 C43 1.5105(17) . ?
O42 C49 1.4341(15) . ?
C43 C51 1.3935(17) . ?
C43 C44 1.3977(16) . ?
O43 C50 1.4315(16) . ?
C44 C54 1.3950(17) . ?
C44 C45 1.5168(16) . ?
C45 C55 1.5153(15) . ?
C45 H45 0.979(15) . ?
C46 O46 1.2092(15) . ?
C46 N46 1.3680(15) . ?
N46 C47 1.4022(15) . ?
N46 C65 1.4572(14) . ?
C47 C61 1.3804(17) . ?
C47 C48 1.3988(16) . ?
C48 C64 1.3825(17) . ?
C49 C50 1.516(2) . ?
C49 H49A 0.995(16) . ?
C49 H49B 1.014(17) . ?
C50 H50A 0.98(2) . ?
C50 H50B 1.05(2) . ?
C51 C52 1.3858(18) . ?
C51 H51 0.988(14) . ?
C52 C53 1.3887(18) . ?
C52 H52 0.986(15) . ?
C53 C54 1.3872(17) . ?
C53 H53 0.981(16) . ?
C54 H54 0.969(15) . ?
C55 C56 1.3916(18) . ?
C55 C60 1.3988(17) . ?
C56 C57 1.3914(17) . ?
C56 H56 0.980(15) . ?
C57 C58 1.3837(19) . ?
C57 H57 0.966(17) . ?
C58 C59 1.3887(19) . ?
C58 H58 0.949(16) . ?
C59 C60 1.3916(17) . ?
C59 H59 0.991(16) . ?
C60 H60 0.978(15) . ?
C61 C62 1.3954(18) . ?
C61 H61 0.981(15) . ?
C62 C63 1.3886(18) . ?
C62 H62 0.967(15) . ?
C63 C64 1.3964(18) . ?
C63 H63 0.960(16) . ?
C64 H64 0.974(16) . ?
C65 C66 1.5146(15) . ?
C65 H65A 0.995(15) . ?
C65 H65B 0.965(15) . ?
C66 C71 1.3920(17) . ?
C66 C67 1.3943(17) . ?
C67 C68 1.3909(17) . ?
C67 H67 0.976(15) . ?
C68 C69 1.3859(18) . ?
C68 H68 0.968(15) . ?
C69 C70 1.3901(18) . ?
C69 H69 0.977(15) . ?
C70 C71 1.3873(17) . ?
C70 H70 0.993(15) . ?
C71 H71 0.956(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 116.97(9) . . ?
O1 C1 C6 105.24(9) . . ?
C8 C1 C6 102.22(9) . . ?
O1 C1 C5 106.89(9) . . ?
C8 C1 C5 114.67(9) . . ?
C6 C1 C5 110.29(9) . . ?
C2 O1 C1 117.70(9) . . ?
O3 C2 O2 105.90(9) . . ?
O3 C2 O1 105.85(9) . . ?
O2 C2 O1 109.16(9) . . ?
O3 C2 C3 111.16(9) . . ?
O2 C2 C3 109.66(9) . . ?
O1 C2 C3 114.70(10) . . ?
C2 O2 C9 105.01(9) . . ?
C11 C3 C4 120.40(11) . . ?
C11 C3 C2 118.45(11) . . ?
C4 C3 C2 121.13(10) . . ?
C2 O3 C10 108.19(10) . . ?
C14 C4 C3 118.88(11) . . ?
C14 C4 C5 123.20(11) . . ?
C3 C4 C5 117.88(11) . . ?
C15 C5 C4 116.84(10) . . ?
C15 C5 C1 113.81(9) . . ?
C4 C5 C1 106.30(9) . . ?
C15 C5 H5 107.0(8) . . ?
C4 C5 H5 107.1(8) . . ?
C1 C5 H5 105.0(8) . . ?
O6 C6 N6 126.48(11) . . ?
O6 C6 C1 125.73(10) . . ?
N6 C6 C1 107.78(9) . . ?
C6 N6 C7 111.03(9) . . ?
C6 N6 C25 124.25(10) . . ?
C7 N6 C25 123.54(10) . . ?
C24 C7 C8 122.72(11) . . ?
C24 C7 N6 126.66(11) . . ?
C8 C7 N6 110.61(10) . . ?
C21 C8 C7 118.96(11) . . ?
C21 C8 C1 133.25(11) . . ?
C7 C8 C1 107.73(10) . . ?
O2 C9 C10 102.70(11) . . ?
O2 C9 H9A 109.6(9) . . ?
C10 C9 H9A 111.9(9) . . ?
O2 C9 H9B 109.0(10) . . ?
C10 C9 H9B 115.1(10) . . ?
H9A C9 H9B 108.3(13) . . ?
O3 C10 C9 104.56(11) . . ?
O3 C10 H10A 109.0(11) . . ?
C9 C10 H10A 112.2(11) . . ?
O3 C10 H10B 110.5(12) . . ?
C9 C10 H10B 112.2(12) . . ?
H10A C10 H10B 108.4(16) . . ?
C12 C11 C3 120.20(12) . . ?
C12 C11 H11 122.1(9) . . ?
C3 C11 H11 117.7(9) . . ?
C11 C12 C13 119.65(12) . . ?
C11 C12 H12 120.2(9) . . ?
C13 C12 H12 120.1(9) . . ?
C14 C13 C12 120.32(12) . . ?
C14 C13 H13 119.0(9) . . ?
C12 C13 H13 120.7(9) . . ?
C13 C14 C4 120.54(12) . . ?
C13 C14 H14 119.5(8) . . ?
C4 C14 H14 120.0(8) . . ?
C20 C15 C16 118.41(11) . . ?
C20 C15 C5 118.31(11) . . ?
C16 C15 C5 123.26(10) . . ?
C17 C16 C15 120.37(11) . . ?
C17 C16 H16 119.5(9) . . ?
C15 C16 H16 120.2(9) . . ?
C18 C17 C16 120.46(12) . . ?
C18 C17 H17 119.8(9) . . ?
C16 C17 H17 119.7(9) . . ?
C19 C18 C17 119.53(12) . . ?
C19 C18 H18 121.3(9) . . ?
C17 C18 H18 119.2(9) . . ?
C18 C19 C20 120.14(12) . . ?
C18 C19 H19 119.6(9) . . ?
C20 C19 H19 120.3(9) . . ?
C19 C20 C15 121.08(12) . . ?
C19 C20 H20 121.2(8) . . ?
C15 C20 H20 117.7(8) . . ?
C8 C21 C22 119.14(11) . . ?
C8 C21 H21 121.3(8) . . ?
C22 C21 H21 119.6(8) . . ?
C23 C22 C21 120.77(11) . . ?
C23 C22 H22 119.0(9) . . ?
C21 C22 H22 120.2(9) . . ?
C22 C23 C24 120.77(11) . . ?
C22 C23 H23 119.7(9) . . ?
C24 C23 H23 119.5(9) . . ?
C7 C24 C23 117.61(11) . . ?
C7 C24 H24 119.6(9) . . ?
C23 C24 H24 122.8(9) . . ?
N6 C25 C26 114.55(10) . . ?
N6 C25 H25A 107.5(9) . . ?
C26 C25 H25A 110.5(9) . . ?
N6 C25 H25B 105.8(8) . . ?
C26 C25 H25B 110.4(8) . . ?
H25A C25 H25B 107.8(12) . . ?
C27 C26 C31 119.11(11) . . ?
C27 C26 C25 122.35(11) . . ?
C31 C26 C25 118.51(11) . . ?
C26 C27 C28 120.36(11) . . ?
C26 C27 H27 118.4(9) . . ?
C28 C27 H27 121.2(9) . . ?
C29 C28 C27 120.23(12) . . ?
C29 C28 H28 120.0(9) . . ?
C27 C28 H28 119.8(9) . . ?
C28 C29 C30 119.66(12) . . ?
C28 C29 H29 120.6(9) . . ?
C30 C29 H29 119.7(9) . . ?
C31 C30 C29 120.24(12) . . ?
C31 C30 H30 119.1(9) . . ?
C29 C30 H30 120.7(9) . . ?
C30 C31 C26 120.39(12) . . ?
C30 C31 H31 121.5(9) . . ?
C26 C31 H31 118.1(9) . . ?
O41 C41 C48 116.34(9) . . ?
O41 C41 C46 105.94(9) . . ?
C48 C41 C46 102.19(9) . . ?
O41 C41 C45 106.97(9) . . ?
C48 C41 C45 115.74(9) . . ?
C46 C41 C45 108.95(9) . . ?
C42 O41 C41 118.62(9) . . ?
O43 C42 O42 105.90(9) . . ?
O43 C42 O41 106.02(9) . . ?
O42 C42 O41 108.74(9) . . ?
O43 C42 C43 110.57(9) . . ?
O42 C42 C43 109.87(10) . . ?
O41 C42 C43 115.29(9) . . ?
C42 O42 C49 104.11(9) . . ?
C51 C43 C44 120.38(11) . . ?
C51 C43 C42 118.95(10) . . ?
C44 C43 C42 120.66(11) . . ?
C42 O43 C50 107.67(10) . . ?
C54 C44 C43 118.72(11) . . ?
C54 C44 C45 123.81(10) . . ?
C43 C44 C45 117.47(10) . . ?
C55 C45 C44 116.31(10) . . ?
C55 C45 C41 114.62(9) . . ?
C44 C45 C41 107.08(9) . . ?
C55 C45 H45 106.4(8) . . ?
C44 C45 H45 107.9(8) . . ?
C41 C45 H45 103.6(8) . . ?
O46 C46 N46 126.52(11) . . ?
O46 C46 C41 125.99(11) . . ?
N46 C46 C41 107.44(10) . . ?
C46 N46 C47 111.32(9) . . ?
C46 N46 C65 123.58(10) . . ?
C47 N46 C65 123.89(10) . . ?
C61 C47 C48 122.68(11) . . ?
C61 C47 N46 127.00(11) . . ?
C48 C47 N46 110.32(10) . . ?
C64 C48 C47 119.09(11) . . ?
C64 C48 C41 132.94(11) . . ?
C47 C48 C41 107.97(10) . . ?
O42 C49 C50 102.89(10) . . ?
O42 C49 H49A 107.6(9) . . ?
C50 C49 H49A 114.7(9) . . ?
O42 C49 H49B 109.3(9) . . ?
C50 C49 H49B 111.4(10) . . ?
H49A C49 H49B 110.5(13) . . ?
O43 C50 C49 104.45(11) . . ?
O43 C50 H50A 110.1(12) . . ?
C49 C50 H50A 111.4(12) . . ?
O43 C50 H50B 106.2(11) . . ?
C49 C50 H50B 111.8(11) . . ?
H50A C50 H50B 112.5(16) . . ?
C52 C51 C43 120.26(11) . . ?
C52 C51 H51 121.6(8) . . ?
C43 C51 H51 118.1(8) . . ?
C51 C52 C53 119.68(11) . . ?
C51 C52 H52 121.0(8) . . ?
C53 C52 H52 119.3(8) . . ?
C54 C53 C52 120.21(11) . . ?
C54 C53 H53 120.2(9) . . ?
C52 C53 H53 119.5(9) . . ?
C53 C54 C44 120.73(11) . . ?
C53 C54 H54 119.6(9) . . ?
C44 C54 H54 119.7(9) . . ?
C56 C55 C60 118.71(11) . . ?
C56 C55 C45 118.31(11) . . ?
C60 C55 C45 122.98(11) . . ?
C57 C56 C55 121.03(12) . . ?
C57 C56 H56 120.8(9) . . ?
C55 C56 H56 118.2(9) . . ?
C58 C57 C56 119.94(12) . . ?
C58 C57 H57 120.6(9) . . ?
C56 C57 H57 119.5(9) . . ?
C57 C58 C59 119.61(11) . . ?
C57 C58 H58 119.5(9) . . ?
C59 C58 H58 120.8(9) . . ?
C58 C59 C60 120.62(12) . . ?
C58 C59 H59 119.3(9) . . ?
C60 C59 H59 120.0(9) . . ?
C59 C60 C55 120.06(11) . . ?
C59 C60 H60 119.1(8) . . ?
C55 C60 H60 120.8(8) . . ?
C47 C61 C62 117.39(11) . . ?
C47 C61 H61 121.2(9) . . ?
C62 C61 H61 121.4(9) . . ?
C63 C62 C61 120.98(11) . . ?
C63 C62 H62 120.3(8) . . ?
C61 C62 H62 118.7(8) . . ?
C62 C63 C64 120.56(12) . . ?
C62 C63 H63 119.5(9) . . ?
C64 C63 H63 120.0(9) . . ?
C48 C64 C63 119.27(11) . . ?
C48 C64 H64 121.4(9) . . ?
C63 C64 H64 119.4(9) . . ?
N46 C65 C66 113.25(9) . . ?
N46 C65 H65A 105.4(8) . . ?
C66 C65 H65A 110.1(8) . . ?
N46 C65 H65B 109.2(8) . . ?
C66 C65 H65B 110.0(8) . . ?
H65A C65 H65B 108.8(12) . . ?
C71 C66 C67 119.34(11) . . ?
C71 C66 C65 121.24(10) . . ?
C67 C66 C65 119.32(10) . . ?
C68 C67 C66 120.19(11) . . ?
C68 C67 H67 121.4(8) . . ?
C66 C67 H67 118.4(8) . . ?
C69 C68 C67 120.08(11) . . ?
C69 C68 H68 121.3(9) . . ?
C67 C68 H68 118.6(9) . . ?
C68 C69 C70 119.98(11) . . ?
C68 C69 H69 119.8(9) . . ?
C70 C69 H69 120.2(9) . . ?
C71 C70 C69 119.98(11) . . ?
C71 C70 H70 119.9(8) . . ?
C69 C70 H70 120.2(8) . . ?
C70 C71 C66 120.42(11) . . ?
C70 C71 H71 120.3(9) . . ?
C66 C71 H71 119.3(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 O1 C2 -70.52(13) . . . . ?
C6 C1 O1 C2 176.85(9) . . . . ?
C5 C1 O1 C2 59.57(12) . . . . ?
C1 O1 C2 O3 -144.02(9) . . . . ?
C1 O1 C2 O2 102.39(11) . . . . ?
C1 O1 C2 C3 -21.10(14) . . . . ?
O3 C2 O2 C9 -36.67(12) . . . . ?
O1 C2 O2 C9 76.88(11) . . . . ?
C3 C2 O2 C9 -156.69(10) . . . . ?
O3 C2 C3 C11 -72.88(13) . . . . ?
O2 C2 C3 C11 43.88(14) . . . . ?
O1 C2 C3 C11 167.10(10) . . . . ?
O3 C2 C3 C4 108.89(12) . . . . ?
O2 C2 C3 C4 -134.35(11) . . . . ?
O1 C2 C3 C4 -11.13(15) . . . . ?
O2 C2 O3 C10 22.72(13) . . . . ?
O1 C2 O3 C10 -93.10(11) . . . . ?
C3 C2 O3 C10 141.76(11) . . . . ?
C11 C3 C4 C14 0.16(17) . . . . ?
C2 C3 C4 C14 178.36(10) . . . . ?
C11 C3 C4 C5 -177.69(10) . . . . ?
C2 C3 C4 C5 0.51(16) . . . . ?
C14 C4 C5 C15 -12.99(16) . . . . ?
C3 C4 C5 C15 164.76(10) . . . . ?
C14 C4 C5 C1 -141.26(11) . . . . ?
C3 C4 C5 C1 36.49(13) . . . . ?
O1 C1 C5 C15 165.21(9) . . . . ?
C8 C1 C5 C15 -63.41(13) . . . . ?
C6 C1 C5 C15 51.30(12) . . . . ?
O1 C1 C5 C4 -64.76(11) . . . . ?
C8 C1 C5 C4 66.62(12) . . . . ?
C6 C1 C5 C4 -178.67(9) . . . . ?
O1 C1 C6 O6 -50.55(15) . . . . ?
C8 C1 C6 O6 -173.23(12) . . . . ?
C5 C1 C6 O6 64.41(15) . . . . ?
O1 C1 C6 N6 130.62(10) . . . . ?
C8 C1 C6 N6 7.94(12) . . . . ?
C5 C1 C6 N6 -114.42(10) . . . . ?
O6 C6 N6 C7 174.53(12) . . . . ?
C1 C6 N6 C7 -6.65(13) . . . . ?
O6 C6 N6 C25 6.61(19) . . . . ?
C1 C6 N6 C25 -174.58(10) . . . . ?
C6 N6 C7 C24 -177.81(12) . . . . ?
C25 N6 C7 C24 -9.78(18) . . . . ?
C6 N6 C7 C8 2.41(13) . . . . ?
C25 N6 C7 C8 170.43(10) . . . . ?
C24 C7 C8 C21 0.95(18) . . . . ?
N6 C7 C8 C21 -179.26(10) . . . . ?
C24 C7 C8 C1 -176.75(11) . . . . ?
N6 C7 C8 C1 3.04(13) . . . . ?
O1 C1 C8 C21 61.93(17) . . . . ?
C6 C1 C8 C21 176.27(13) . . . . ?
C5 C1 C8 C21 -64.40(17) . . . . ?
O1 C1 C8 C7 -120.83(11) . . . . ?
C6 C1 C8 C7 -6.49(12) . . . . ?
C5 C1 C8 C7 112.84(11) . . . . ?
C2 O2 C9 C10 35.10(13) . . . . ?
C2 O3 C10 C9 -0.59(14) . . . . ?
O2 C9 C10 O3 -20.98(14) . . . . ?
C4 C3 C11 C12 0.04(18) . . . . ?
C2 C3 C11 C12 -178.20(11) . . . . ?
C3 C11 C12 C13 0.48(18) . . . . ?
C11 C12 C13 C14 -1.22(19) . . . . ?
C12 C13 C14 C4 1.43(18) . . . . ?
C3 C4 C14 C13 -0.90(17) . . . . ?
C5 C4 C14 C13 176.84(11) . . . . ?
C4 C5 C15 C20 132.92(11) . . . . ?
C1 C5 C15 C20 -102.54(12) . . . . ?
C4 C5 C15 C16 -48.76(16) . . . . ?
C1 C5 C15 C16 75.78(14) . . . . ?
C20 C15 C16 C17 -0.50(18) . . . . ?
C5 C15 C16 C17 -178.82(11) . . . . ?
C15 C16 C17 C18 1.36(19) . . . . ?
C16 C17 C18 C19 -0.90(19) . . . . ?
C17 C18 C19 C20 -0.41(19) . . . . ?
C18 C19 C20 C15 1.28(19) . . . . ?
C16 C15 C20 C19 -0.82(18) . . . . ?
C5 C15 C20 C19 177.59(11) . . . . ?
C7 C8 C21 C22 0.21(17) . . . . ?
C1 C8 C21 C22 177.20(12) . . . . ?
C8 C21 C22 C23 -0.77(19) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C8 C7 C24 C23 -1.49(18) . . . . ?
N6 C7 C24 C23 178.75(11) . . . . ?
C22 C23 C24 C7 0.89(19) . . . . ?
C6 N6 C25 C26 -121.54(12) . . . . ?
C7 N6 C25 C26 72.01(14) . . . . ?
N6 C25 C26 C27 12.83(16) . . . . ?
N6 C25 C26 C31 -168.96(10) . . . . ?
C31 C26 C27 C28 0.08(17) . . . . ?
C25 C26 C27 C28 178.29(11) . . . . ?
C26 C27 C28 C29 -0.34(18) . . . . ?
C27 C28 C29 C30 0.22(18) . . . . ?
C28 C29 C30 C31 0.16(18) . . . . ?
C29 C30 C31 C26 -0.42(18) . . . . ?
C27 C26 C31 C30 0.29(17) . . . . ?
C25 C26 C31 C30 -177.98(11) . . . . ?
C48 C41 O41 C42 75.45(13) . . . . ?
C46 C41 O41 C42 -171.82(9) . . . . ?
C45 C41 O41 C42 -55.69(13) . . . . ?
C41 O41 C42 O43 139.41(10) . . . . ?
C41 O41 C42 O42 -107.12(11) . . . . ?
C41 O41 C42 C43 16.74(15) . . . . ?
O43 C42 O42 C49 39.18(12) . . . . ?
O41 C42 O42 C49 -74.37(11) . . . . ?
C43 C42 O42 C49 158.61(10) . . . . ?
O43 C42 C43 C51 73.55(14) . . . . ?
O42 C42 C43 C51 -42.97(14) . . . . ?
O41 C42 C43 C51 -166.23(11) . . . . ?
O43 C42 C43 C44 -106.45(12) . . . . ?
O42 C42 C43 C44 137.02(11) . . . . ?
O41 C42 C43 C44 13.76(16) . . . . ?
O42 C42 O43 C50 -26.51(13) . . . . ?
O41 C42 O43 C50 88.91(12) . . . . ?
C43 C42 O43 C50 -145.47(11) . . . . ?
C51 C43 C44 C54 0.19(17) . . . . ?
C42 C43 C44 C54 -179.80(10) . . . . ?
C51 C43 C44 C45 179.70(10) . . . . ?
C42 C43 C44 C45 -0.29(16) . . . . ?
C54 C44 C45 C55 11.99(16) . . . . ?
C43 C44 C45 C55 -167.50(10) . . . . ?
C54 C44 C45 C41 141.65(11) . . . . ?
C43 C44 C45 C41 -37.84(14) . . . . ?
O41 C41 C45 C55 -165.10(9) . . . . ?
C48 C41 C45 C55 63.43(13) . . . . ?
C46 C41 C45 C55 -51.00(13) . . . . ?
O41 C41 C45 C44 64.28(11) . . . . ?
C48 C41 C45 C44 -67.18(12) . . . . ?
C46 C41 C45 C44 178.39(9) . . . . ?
O41 C41 C46 O46 51.37(15) . . . . ?
C48 C41 C46 O46 173.63(11) . . . . ?
C45 C41 C46 O46 -63.41(14) . . . . ?
O41 C41 C46 N46 -130.92(9) . . . . ?
C48 C41 C46 N46 -8.65(11) . . . . ?
C45 C41 C46 N46 114.30(10) . . . . ?
O46 C46 N46 C47 -174.70(11) . . . . ?
C41 C46 N46 C47 7.60(12) . . . . ?
O46 C46 N46 C65 -6.80(18) . . . . ?
C41 C46 N46 C65 175.50(9) . . . . ?
C46 N46 C47 C61 176.11(11) . . . . ?
C65 N46 C47 C61 8.25(17) . . . . ?
C46 N46 C47 C48 -3.22(13) . . . . ?
C65 N46 C47 C48 -171.07(10) . . . . ?
C61 C47 C48 C64 -2.02(17) . . . . ?
N46 C47 C48 C64 177.34(10) . . . . ?
C61 C47 C48 C41 177.86(10) . . . . ?
N46 C47 C48 C41 -2.78(12) . . . . ?
O41 C41 C48 C64 -58.50(17) . . . . ?
C46 C41 C48 C64 -173.37(12) . . . . ?
C45 C41 C48 C64 68.40(16) . . . . ?
O41 C41 C48 C47 121.65(10) . . . . ?
C46 C41 C48 C47 6.78(11) . . . . ?
C45 C41 C48 C47 -111.45(11) . . . . ?
C42 O42 C49 C50 -35.35(12) . . . . ?
C42 O43 C50 C49 3.90(14) . . . . ?
O42 C49 C50 O43 19.30(14) . . . . ?
C44 C43 C51 C52 -0.74(18) . . . . ?
C42 C43 C51 C52 179.25(11) . . . . ?
C43 C51 C52 C53 0.38(19) . . . . ?
C51 C52 C53 C54 0.54(19) . . . . ?
C52 C53 C54 C44 -1.10(18) . . . . ?
C43 C44 C54 C53 0.73(17) . . . . ?
C45 C44 C54 C53 -178.75(11) . . . . ?
C44 C45 C55 C56 -126.99(11) . . . . ?
C41 C45 C55 C56 107.07(12) . . . . ?
C44 C45 C55 C60 52.54(15) . . . . ?
C41 C45 C55 C60 -73.41(14) . . . . ?
C60 C55 C56 C57 -1.65(17) . . . . ?
C45 C55 C56 C57 177.90(11) . . . . ?
C55 C56 C57 C58 0.33(18) . . . . ?
C56 C57 C58 C59 1.10(18) . . . . ?
C57 C58 C59 C60 -1.19(18) . . . . ?
C58 C59 C60 C55 -0.14(18) . . . . ?
C56 C55 C60 C59 1.55(17) . . . . ?
C45 C55 C60 C59 -177.98(10) . . . . ?
C48 C47 C61 C62 1.02(17) . . . . ?
N46 C47 C61 C62 -178.23(11) . . . . ?
C47 C61 C62 C63 0.46(18) . . . . ?
C61 C62 C63 C64 -0.92(18) . . . . ?
C47 C48 C64 C63 1.50(17) . . . . ?
C41 C48 C64 C63 -178.34(11) . . . . ?
C62 C63 C64 C48 -0.09(18) . . . . ?
C46 N46 C65 C66 125.52(11) . . . . ?
C47 N46 C65 C66 -68.09(14) . . . . ?
N46 C65 C66 C71 -33.79(16) . . . . ?
N46 C65 C66 C67 149.68(11) . . . . ?
C71 C66 C67 C68 -1.01(17) . . . . ?
C65 C66 C67 C68 175.59(11) . . . . ?
C66 C67 C68 C69 0.57(18) . . . . ?
C67 C68 C69 C70 -0.02(18) . . . . ?
C68 C69 C70 C71 -0.08(18) . . . . ?
C69 C70 C71 C66 -0.37(18) . . . . ?
C67 C66 C71 C70 0.91(17) . . . . ?
C65 C66 C71 C70 -175.62(11) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.040


# start Validation Reply Form
_vrf_PLAT029_JF2999FMI           
;
PROBLEM: 029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low 0.943
RESPONSE: Data were collected on a fixed Chi, 3-circle diffractometer, 
and the system is triclinic therefore limiting access to the full sphere
of reflection.
;

_vrf_PLAT911_JF2999FMI           
;
PROBLEM: 11_ALERT_3_B Missing FCF Refl Between Thmin & STh/L= 0.600;  473
RESPONSE: Data were collected on a fixed Chi, 3-circle diffractometer, 
and the system is triclinic therefore limiting access to the full sphere
of reflection.
;

# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2998FMI
_database_code_depnum_ccdc_archive 'CCDC 2087129'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 O4'
_chemical_formula_sum            'C22 H18 O4'
_chemical_formula_weight         346.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.7117(6)
_cell_length_b                   17.1656(11)
_cell_length_c                   19.8546(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3309.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.71

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28507
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3807
_reflns_number_gt                3347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+1.7308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0115(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22031(13) 0.50233(7) 0.59566(6) 0.0186(3) Uani 1 1 d . . . . .
O1 O 0.36278(9) 0.51023(5) 0.58165(4) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.45722(13) 0.48615(7) 0.63432(6) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.15591(10) 0.50878(5) 0.53292(5) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.43865(13) 0.39720(7) 0.64767(6) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.4833(16) 0.3873(9) 0.6906(8) 0.018(4) Uiso 1 1 d . . . . .
O3 O 0.17153(9) 0.56418(5) 0.63510(5) 0.0210(2) Uani 1 1 d . . . . .
C4 C 0.28668(13) 0.37782(7) 0.65551(6) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.18476(13) 0.42659(7) 0.63027(6) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.12560(16) 0.59045(8) 0.52249(7) 0.0268(3) Uani 1 1 d . . . . .
H6A H 0.029(2) 0.5942(11) 0.5101(9) 0.035(5) Uiso 1 1 d . . . . .
H6B H 0.189(2) 0.6107(11) 0.4870(10) 0.041(5) Uiso 1 1 d . . . . .
C7 C 0.15574(16) 0.62896(8) 0.58990(7) 0.0262(3) Uani 1 1 d . . . . .
H7A H 0.2428(19) 0.6586(10) 0.5905(9) 0.030(4) Uiso 1 1 d . . . . .
H7B H 0.083(2) 0.6619(11) 0.6064(10) 0.038(5) Uiso 1 1 d . . . . .
C8 C 0.43095(14) 0.53016(8) 0.69904(6) 0.0210(3) Uani 1 1 d . . . . .
H8 H 0.3470(18) 0.5179(9) 0.7230(9) 0.024(4) Uiso 1 1 d . . . . .
C9 C 0.51804(15) 0.58164(8) 0.72488(7) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.4997(17) 0.6097(10) 0.7658(9) 0.028(4) Uiso 1 1 d . . . . .
C10 C 0.64853(15) 0.60116(8) 0.69118(7) 0.0254(3) Uani 1 1 d . . . . .
O10 O 0.72255(13) 0.65457(6) 0.71095(6) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.68432(14) 0.55481(8) 0.63110(7) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.7741(17) 0.5649(9) 0.6119(8) 0.022(4) Uiso 1 1 d . . . . .
C12 C 0.59606(13) 0.50412(7) 0.60426(7) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.6175(18) 0.4780(10) 0.5628(9) 0.028(4) Uiso 1 1 d . . . . .
C13 C 0.50334(13) 0.34456(7) 0.59480(6) 0.0185(3) Uani 1 1 d . . . . .
C14 C 0.60841(13) 0.29352(7) 0.61306(7) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.6396(17) 0.2933(10) 0.6589(9) 0.026(4) Uiso 1 1 d . . . . .
C15 C 0.66655(14) 0.24355(8) 0.56581(7) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.7383(19) 0.2080(11) 0.5801(9) 0.032(4) Uiso 1 1 d . . . . .
C16 C 0.62127(14) 0.24408(8) 0.49968(7) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.6591(16) 0.2105(9) 0.4671(8) 0.021(4) Uiso 1 1 d . . . . .
C17 C 0.51706(14) 0.29518(8) 0.48103(7) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.4845(17) 0.2966(10) 0.4356(9) 0.027(4) Uiso 1 1 d . . . . .
C18 C 0.45753(14) 0.34471(8) 0.52806(7) 0.0222(3) Uani 1 1 d . . . . .
H18 H 0.3838(18) 0.3791(10) 0.5144(8) 0.027(4) Uiso 1 1 d . . . . .
C19 C 0.24819(14) 0.30802(8) 0.68701(6) 0.0217(3) Uani 1 1 d . . . . .
H19 H 0.3175(17) 0.2736(9) 0.7052(8) 0.021(4) Uiso 1 1 d . . . . .
C20 C 0.11071(15) 0.28791(8) 0.69291(7) 0.0248(3) Uani 1 1 d . . . . .
H20 H 0.0876(17) 0.2388(10) 0.7141(8) 0.026(4) Uiso 1 1 d . . . . .
C21 C 0.00894(14) 0.33759(8) 0.66831(7) 0.0248(3) Uani 1 1 d . . . . .
H21 H -0.085(2) 0.3244(11) 0.6729(9) 0.036(5) Uiso 1 1 d . . . . .
C22 C 0.04582(14) 0.40695(8) 0.63749(6) 0.0224(3) Uani 1 1 d . . . . .
H22 H -0.0238(17) 0.4426(10) 0.6208(9) 0.025(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.3983(15) . ?
C1 O3 1.4016(15) . ?
C1 O1 1.4178(15) . ?
C1 C5 1.5106(17) . ?
O1 C2 1.4509(15) . ?
C2 C12 1.5065(18) . ?
C2 C8 1.5123(17) . ?
C2 C3 1.5602(17) . ?
O2 C6 1.4475(16) . ?
C3 C13 1.5209(17) . ?
C3 C4 1.5209(17) . ?
C3 H3 0.971(16) . ?
O3 C7 1.4371(16) . ?
C4 C5 1.3898(18) . ?
C4 C19 1.4023(18) . ?
C5 C22 1.3981(18) . ?
C6 C7 1.521(2) . ?
C6 H6A 0.968(19) . ?
C6 H6B 1.00(2) . ?
C7 H7A 0.987(19) . ?
C7 H7B 0.96(2) . ?
C8 C9 1.3265(19) . ?
C8 H8 0.967(18) . ?
C9 C10 1.472(2) . ?
C9 H9 0.962(18) . ?
C10 O10 1.2293(17) . ?
C10 C11 1.475(2) . ?
C11 C12 1.3327(19) . ?
C11 H11 0.967(17) . ?
C12 H12 0.960(18) . ?
C13 C14 1.3928(17) . ?
C13 C18 1.3977(18) . ?
C14 C15 1.3910(19) . ?
C14 H14 0.959(17) . ?
C15 C16 1.385(2) . ?
C15 H15 0.969(19) . ?
C16 C17 1.3895(19) . ?
C16 H16 0.941(16) . ?
C17 C18 1.3890(19) . ?
C17 H17 0.957(17) . ?
C18 H18 0.967(18) . ?
C19 C20 1.384(2) . ?
C19 H19 0.966(17) . ?
C20 C21 1.394(2) . ?
C20 H20 0.968(17) . ?
C21 C22 1.3858(19) . ?
C21 H21 0.95(2) . ?
C22 H22 0.970(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O3 106.65(10) . . ?
O2 C1 O1 104.72(10) . . ?
O3 C1 O1 111.53(10) . . ?
O2 C1 C5 111.78(10) . . ?
O3 C1 C5 108.70(10) . . ?
O1 C1 C5 113.24(10) . . ?
C1 O1 C2 116.63(9) . . ?
O1 C2 C12 102.82(10) . . ?
O1 C2 C8 111.31(10) . . ?
C12 C2 C8 112.67(11) . . ?
O1 C2 C3 109.16(10) . . ?
C12 C2 C3 111.78(10) . . ?
C8 C2 C3 108.96(10) . . ?
C1 O2 C6 107.16(10) . . ?
C13 C3 C4 109.97(10) . . ?
C13 C3 C2 114.61(10) . . ?
C4 C3 C2 110.09(10) . . ?
C13 C3 H3 108.5(9) . . ?
C4 C3 H3 107.8(9) . . ?
C2 C3 H3 105.6(9) . . ?
C1 O3 C7 105.86(10) . . ?
C5 C4 C19 119.05(12) . . ?
C5 C4 C3 121.50(11) . . ?
C19 C4 C3 119.42(11) . . ?
C4 C5 C22 120.34(12) . . ?
C4 C5 C1 121.31(11) . . ?
C22 C5 C1 118.34(11) . . ?
O2 C6 C7 104.82(11) . . ?
O2 C6 H6A 107.2(11) . . ?
C7 C6 H6A 112.3(11) . . ?
O2 C6 H6B 108.3(11) . . ?
C7 C6 H6B 110.6(11) . . ?
H6A C6 H6B 113.1(15) . . ?
O3 C7 C6 103.51(11) . . ?
O3 C7 H7A 107.5(10) . . ?
C6 C7 H7A 113.6(10) . . ?
O3 C7 H7B 108.7(12) . . ?
C6 C7 H7B 114.4(12) . . ?
H7A C7 H7B 108.8(15) . . ?
C9 C8 C2 123.63(13) . . ?
C9 C8 H8 119.5(10) . . ?
C2 C8 H8 116.9(10) . . ?
C8 C9 C10 121.66(13) . . ?
C8 C9 H9 122.9(10) . . ?
C10 C9 H9 115.4(10) . . ?
O10 C10 C9 121.88(14) . . ?
O10 C10 C11 121.50(14) . . ?
C9 C10 C11 116.59(12) . . ?
C12 C11 C10 121.60(13) . . ?
C12 C11 H11 122.6(10) . . ?
C10 C11 H11 115.8(10) . . ?
C11 C12 C2 123.43(13) . . ?
C11 C12 H12 120.5(11) . . ?
C2 C12 H12 116.0(11) . . ?
C14 C13 C18 118.76(12) . . ?
C14 C13 C3 119.78(11) . . ?
C18 C13 C3 121.45(11) . . ?
C15 C14 C13 120.65(12) . . ?
C15 C14 H14 120.6(10) . . ?
C13 C14 H14 118.7(10) . . ?
C16 C15 C14 120.43(12) . . ?
C16 C15 H15 120.7(10) . . ?
C14 C15 H15 118.9(10) . . ?
C15 C16 C17 119.22(12) . . ?
C15 C16 H16 121.6(10) . . ?
C17 C16 H16 119.2(10) . . ?
C18 C17 C16 120.69(13) . . ?
C18 C17 H17 118.8(10) . . ?
C16 C17 H17 120.5(10) . . ?
C17 C18 C13 120.25(12) . . ?
C17 C18 H18 119.5(10) . . ?
C13 C18 H18 120.2(10) . . ?
C20 C19 C4 120.53(12) . . ?
C20 C19 H19 119.2(10) . . ?
C4 C19 H19 120.2(10) . . ?
C19 C20 C21 120.12(12) . . ?
C19 C20 H20 118.5(10) . . ?
C21 C20 H20 121.3(10) . . ?
C22 C21 C20 119.81(13) . . ?
C22 C21 H21 119.8(11) . . ?
C20 C21 H21 120.4(11) . . ?
C21 C22 C5 120.12(13) . . ?
C21 C22 H22 120.9(10) . . ?
C5 C22 H22 119.0(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 C2 -164.55(9) . . . . ?
O3 C1 O1 C2 80.47(12) . . . . ?
C5 C1 O1 C2 -42.52(14) . . . . ?
C1 O1 C2 C12 -178.44(10) . . . . ?
C1 O1 C2 C8 -57.58(14) . . . . ?
C1 O1 C2 C3 62.74(13) . . . . ?
O3 C1 O2 C6 28.17(13) . . . . ?
O1 C1 O2 C6 -90.17(11) . . . . ?
C5 C1 O2 C6 146.85(11) . . . . ?
O1 C2 C3 C13 76.28(13) . . . . ?
C12 C2 C3 C13 -36.79(15) . . . . ?
C8 C2 C3 C13 -161.97(10) . . . . ?
O1 C2 C3 C4 -48.31(13) . . . . ?
C12 C2 C3 C4 -161.37(10) . . . . ?
C8 C2 C3 C4 73.44(12) . . . . ?
O2 C1 O3 C7 -36.21(13) . . . . ?
O1 C1 O3 C7 77.57(12) . . . . ?
C5 C1 O3 C7 -156.89(10) . . . . ?
C13 C3 C4 C5 -106.29(13) . . . . ?
C2 C3 C4 C5 20.92(16) . . . . ?
C13 C3 C4 C19 71.67(14) . . . . ?
C2 C3 C4 C19 -161.12(11) . . . . ?
C19 C4 C5 C22 1.31(18) . . . . ?
C3 C4 C5 C22 179.27(11) . . . . ?
C19 C4 C5 C1 -179.79(11) . . . . ?
C3 C4 C5 C1 -1.83(18) . . . . ?
O2 C1 C5 C4 128.56(12) . . . . ?
O3 C1 C5 C4 -113.98(12) . . . . ?
O1 C1 C5 C4 10.56(16) . . . . ?
O2 C1 C5 C22 -52.51(15) . . . . ?
O3 C1 C5 C22 64.95(14) . . . . ?
O1 C1 C5 C22 -170.51(11) . . . . ?
C1 O2 C6 C7 -9.49(14) . . . . ?
C1 O3 C7 C6 28.81(14) . . . . ?
O2 C6 C7 O3 -11.73(14) . . . . ?
O1 C2 C8 C9 -112.00(14) . . . . ?
C12 C2 C8 C9 2.90(18) . . . . ?
C3 C2 C8 C9 127.56(13) . . . . ?
C2 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 O10 172.12(13) . . . . ?
C8 C9 C10 C11 -6.15(19) . . . . ?
O10 C10 C11 C12 -170.83(13) . . . . ?
C9 C10 C11 C12 7.44(19) . . . . ?
C10 C11 C12 C2 -3.6(2) . . . . ?
O1 C2 C12 C11 118.36(13) . . . . ?
C8 C2 C12 C11 -1.57(18) . . . . ?
C3 C2 C12 C11 -124.68(13) . . . . ?
C4 C3 C13 C14 -117.53(12) . . . . ?
C2 C3 C13 C14 117.82(13) . . . . ?
C4 C3 C13 C18 60.93(15) . . . . ?
C2 C3 C13 C18 -63.72(16) . . . . ?
C18 C13 C14 C15 -0.10(19) . . . . ?
C3 C13 C14 C15 178.41(12) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C13 1.0(2) . . . . ?
C14 C13 C18 C17 -0.55(19) . . . . ?
C3 C13 C18 C17 -179.03(12) . . . . ?
C5 C4 C19 C20 0.00(18) . . . . ?
C3 C4 C19 C20 -178.00(11) . . . . ?
C4 C19 C20 C21 -0.88(19) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C5 0.85(19) . . . . ?
C4 C5 C22 C21 -1.74(19) . . . . ?
C1 C5 C22 C21 179.32(11) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2983FMI
_database_code_depnum_ccdc_archive 'CCDC 2087128'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N O5'
_chemical_formula_sum            'C23 H19 N O5'
_chemical_formula_weight         389.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   19.1967(9)
_cell_length_b                   13.7962(6)
_cell_length_c                   13.8480(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3667.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      69.27

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.178
_exptl_absorpt_coefficient_mu    0.823
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7343
_exptl_absorpt_correction_T_max  0.8116
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17934
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         69.545
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6717
_reflns_number_gt                6644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.975

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.5555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3066 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6717
_refine_ls_number_parameters     683
_refine_ls_number_restraints     432
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31097(11) 0.50678(15) 0.45596(16) 0.0138(4) Uani 0.91 1 d . U P A 1
O1 O 0.25901(10) 0.45025(15) 0.41277(15) 0.0150(4) Uani 0.91 1 d . U P A 1
C2 C 0.19693(10) 0.50550(14) 0.39463(15) 0.0132(4) Uani 0.91 1 d . U P A 1
H2 H 0.210946 0.569084 0.365925 0.016 Uiso 0.91 1 calc R U P A 1
O2 O 0.34086(8) 0.56997(11) 0.38767(11) 0.0160(3) Uani 0.91 1 d . . P A 1
C3 C 0.16075(11) 0.52560(15) 0.49254(14) 0.0127(4) Uani 0.91 1 d . U P A 1
H3 H 0.120875 0.570686 0.480633 0.015 Uiso 0.91 1 calc R U P A 1
O3 O 0.36389(8) 0.44224(11) 0.48218(11) 0.0173(3) Uani 0.91 1 d . U P A 1
C4 C 0.21295(14) 0.5772(2) 0.55688(19) 0.0155(5) Uani 0.91 1 d . U P A 1
C5 C 0.28446(13) 0.56513(18) 0.53989(18) 0.0150(5) Uani 0.91 1 d . U P A 1
C6 C 0.33278(11) 0.61185(16) 0.59903(17) 0.0162(4) Uani 0.91 1 d . U P A 1
H6 H 0.381233 0.603802 0.587598 0.019 Uiso 0.91 1 calc R U P A 1
C7 C 0.31004(12) 0.67046(16) 0.67505(17) 0.0175(4) Uani 0.91 1 d . U P A 1
H7 H 0.342912 0.701779 0.715743 0.021 Uiso 0.91 1 calc R U P A 1
C8 C 0.23897(15) 0.68273(15) 0.69084(15) 0.0168(4) Uani 0.91 1 d . U P A 1
H8 H 0.223350 0.723009 0.742090 0.020 Uiso 0.91 1 calc R U P A 1
C9 C 0.19112(12) 0.63664(15) 0.63239(16) 0.0156(4) Uani 0.91 1 d . U P A 1
H9 H 0.142737 0.645528 0.643759 0.019 Uiso 0.91 1 calc R U P A 1
C10 C 0.38922(13) 0.51281(17) 0.33211(19) 0.0247(5) Uani 0.91 1 d . U P A 1
H10A H 0.433227 0.548619 0.321283 0.030 Uiso 0.91 1 calc R U P A 1
H10B H 0.369028 0.494850 0.268806 0.030 Uiso 0.91 1 calc R U P A 1
C11 C 0.40156(12) 0.42316(17) 0.39428(17) 0.0208(4) Uani 0.91 1 d . . P A 1
H11A H 0.383484 0.364287 0.361988 0.025 Uiso 0.91 1 calc R U P A 1
H11B H 0.451836 0.414297 0.407503 0.025 Uiso 0.91 1 calc R U P A 1
C12 C 0.15347(11) 0.45192(14) 0.32139(15) 0.0142(4) Uani 0.91 1 d . U P A 1
C13 C 0.09304(11) 0.49501(15) 0.28529(15) 0.0151(4) Uani 0.91 1 d . . P A 1
H13 H 0.078571 0.556070 0.309853 0.018 Uiso 0.91 1 calc R U P A 1
C14 C 0.05389(10) 0.45015(14) 0.21428(15) 0.0150(4) Uani 0.91 1 d . . P A 1
H14 H 0.013093 0.479847 0.189137 0.018 Uiso 0.91 1 calc R U P A 1
C15 C 0.07604(11) 0.36053(14) 0.18096(14) 0.0139(4) Uani 0.91 1 d . . P A 1
N15 N 0.03532(10) 0.31354(16) 0.10507(16) 0.0174(5) Uani 0.91 1 d . . P A 1
O15 O -0.01666(8) 0.35533(12) 0.07454(12) 0.0227(3) Uani 0.91 1 d . . P A 1
C16 C 0.13520(11) 0.31567(15) 0.21501(17) 0.0174(4) Uani 0.91 1 d . . P A 1
H16 H 0.149134 0.254383 0.190420 0.021 Uiso 0.91 1 calc R U P A 1
O16 O 0.05540(8) 0.23465(11) 0.07384(12) 0.0237(4) Uani 0.91 1 d . . P A 1
C17 C 0.17403(11) 0.36165(15) 0.28587(16) 0.0176(4) Uani 0.91 1 d . . P A 1
H17 H 0.214877 0.331565 0.310404 0.021 Uiso 0.91 1 calc R U P A 1
C18 C 0.13213(12) 0.43402(17) 0.54000(19) 0.0160(5) Uani 0.91 1 d . U P A 1
C19 C 0.17393(11) 0.37531(15) 0.59698(16) 0.0178(5) Uani 0.91 1 d . . P A 1
H19 H 0.220852 0.393529 0.609067 0.021 Uiso 0.91 1 calc R U P A 1
C20 C 0.14798(13) 0.29017(16) 0.63660(19) 0.0271(5) Uani 0.91 1 d . . P A 1
H20 H 0.177322 0.250330 0.675022 0.032 Uiso 0.91 1 calc R U P A 1
C21 C 0.08040(16) 0.26343(19) 0.6205(3) 0.0355(8) Uani 0.91 1 d . . P A 1
H21 H 0.062631 0.205714 0.648700 0.043 Uiso 0.91 1 calc R U P A 1
C22 C 0.03718(13) 0.32142(18) 0.5623(2) 0.0300(6) Uani 0.91 1 d . . P A 1
H22 H -0.009507 0.302464 0.549620 0.036 Uiso 0.91 1 calc R U P A 1
C23 C 0.06345(12) 0.40634(17) 0.52378(19) 0.0230(5) Uani 0.91 1 d . . P A 1
H23 H 0.034122 0.446426 0.485597 0.028 Uiso 0.91 1 calc R U P A 1
C31 C 0.18832(13) 0.9928(2) 0.68825(19) 0.0175(6) Uani 0.91 1 d . U P B 1
O31 O 0.24245(8) 0.93637(11) 0.64849(12) 0.0159(3) Uani 0.91 1 d . U P B 1
C32 C 0.30379(10) 0.99329(14) 0.63062(15) 0.0145(4) Uani 0.91 1 d . U P B 1
H32 H 0.288739 1.056100 0.601237 0.017 Uiso 0.91 1 calc R U P B 1
O32 O 0.15870(8) 1.05244(11) 0.61669(12) 0.0203(3) Uani 0.91 1 d . . P B 1
C33 C 0.33763(12) 1.01583(15) 0.72923(16) 0.0147(4) Uani 0.91 1 d . U P B 1
H33 H 0.377340 1.061404 0.718172 0.018 Uiso 0.91 1 calc R U P B 1
O33 O 0.13637(8) 0.92761(11) 0.71540(12) 0.0198(3) Uani 0.91 1 d . U P B 1
C34 C 0.28329(14) 1.06769(19) 0.79040(19) 0.0168(5) Uani 0.91 1 d . U P B 1
C35 C 0.21242(12) 1.05464(15) 0.77125(17) 0.0180(4) Uani 0.91 1 d . U P B 1
C36 C 0.16286(11) 1.10151(16) 0.82833(17) 0.0201(4) Uani 0.91 1 d . . P B 1
H36 H 0.114713 1.093404 0.814662 0.024 Uiso 0.91 1 calc R U P B 1
C37 C 0.18326(14) 1.15966(18) 0.9046(2) 0.0237(5) Uani 0.91 1 d . U P B 1
H37 H 0.149232 1.190991 0.943453 0.028 Uiso 0.91 1 calc R U P B 1
C38 C 0.25402(13) 1.17218(16) 0.92441(18) 0.0228(5) Uani 0.91 1 d . U P B 1
H38 H 0.268323 1.211875 0.976850 0.027 Uiso 0.91 1 calc R U P B 1
C39 C 0.30323(13) 1.12649(15) 0.86728(17) 0.0199(5) Uani 0.91 1 d . U P B 1
H39 H 0.351332 1.135391 0.880729 0.024 Uiso 0.91 1 calc R U P B 1
C40 C 0.10976(14) 0.99323(19) 0.5645(2) 0.0269(5) Uani 0.91 1 d . U P B 1
H40A H 0.128322 0.975715 0.500078 0.032 Uiso 0.91 1 calc R U P B 1
H40B H 0.064866 1.027531 0.556026 0.032 Uiso 0.91 1 calc R U P B 1
C41 C 0.10064(12) 0.90348(19) 0.62709(18) 0.0265(5) Uani 0.91 1 d . . P B 1
H41A H 0.050717 0.890343 0.639323 0.032 Uiso 0.91 1 calc R U P B 1
H41B H 0.121829 0.845946 0.596065 0.032 Uiso 0.91 1 calc R U P B 1
C42 C 0.34878(11) 0.94123(15) 0.55800(15) 0.0157(4) Uani 0.91 1 d . . P B 1
C43 C 0.40956(10) 0.98564(15) 0.52411(16) 0.0161(4) Uani 0.91 1 d . . P B 1
H43 H 0.424319 1.045223 0.551750 0.019 Uiso 0.91 1 calc R U P B 1
C44 C 0.44842(11) 0.94416(15) 0.45108(16) 0.0179(4) Uani 0.91 1 d . . P B 1
H44 H 0.489446 0.974818 0.427864 0.022 Uiso 0.91 1 calc R U P B 1
C45 C 0.42630(11) 0.85704(15) 0.41253(16) 0.0170(4) Uani 0.91 1 d . . P B 1
N45 N 0.46588(11) 0.81507(17) 0.33191(18) 0.0204(5) Uani 0.91 1 d . . P B 1
O45 O 0.51885(8) 0.85692(12) 0.30511(13) 0.0266(4) Uani 0.91 1 d . . P B 1
C46 C 0.36737(12) 0.80985(16) 0.44487(19) 0.0189(5) Uani 0.91 1 d . . P B 1
H46 H 0.353768 0.749428 0.417902 0.023 Uiso 0.91 1 calc R U P B 1
O46 O 0.44383(9) 0.74054(12) 0.29338(13) 0.0281(4) Uani 0.91 1 d . . P B 1
C47 C 0.32847(11) 0.85267(15) 0.51762(17) 0.0179(4) Uani 0.91 1 d . . P B 1
H47 H 0.287503 0.821491 0.540343 0.021 Uiso 0.91 1 calc R U P B 1
C48 C 0.36558(15) 0.9266(2) 0.7821(3) 0.0166(6) Uani 0.91 1 d . . P B 1
C49 C 0.32215(11) 0.87107(15) 0.84050(16) 0.0171(4) Uani 0.91 1 d . . P B 1
H49 H 0.274074 0.886740 0.845122 0.021 Uiso 0.91 1 calc R U P B 1
C50 C 0.34853(12) 0.79293(15) 0.89211(16) 0.0192(4) Uani 0.91 1 d . . P B 1
H50 H 0.318377 0.755235 0.931464 0.023 Uiso 0.91 1 calc R U P B 1
C51 C 0.41861(12) 0.76976(15) 0.88644(17) 0.0206(5) Uani 0.91 1 d . . P B 1
H51 H 0.436916 0.717241 0.922832 0.025 Uiso 0.91 1 calc R U P B 1
C52 C 0.46185(12) 0.82413(18) 0.8270(2) 0.0242(5) Uani 0.91 1 d . . P B 1
H52 H 0.509805 0.807939 0.821812 0.029 Uiso 0.91 1 calc R U P B 1
C53 C 0.43538(11) 0.90221(16) 0.77486(17) 0.0205(5) Uani 0.91 1 d . . P B 1
H53 H 0.465293 0.938895 0.734221 0.025 Uiso 0.91 1 calc R U P B 1
C101 C 0.1865(9) 0.5036(14) 0.4659(14) 0.021(2) Uiso 0.09 1 d D U P C 2
O101 O 0.2413(11) 0.4446(18) 0.421(2) 0.020(4) Uiso 0.09 1 d D U P C 2
C102 C 0.3029(11) 0.4989(18) 0.4039(16) 0.034(3) Uiso 0.09 1 d D U P C 2
H10C H 0.290056 0.562459 0.374077 0.040 Uiso 0.09 1 calc R U P C 2
O102 O 0.1602(10) 0.5570(14) 0.3884(15) 0.042(3) Uiso 0.09 1 d D U P C 2
C103 C 0.3367(11) 0.5170(17) 0.5013(15) 0.028(3) Uiso 0.09 1 d D U P C 2
H103 H 0.377354 0.560113 0.487000 0.033 Uiso 0.09 1 calc R U P C 2
O103 O 0.1389(11) 0.4339(15) 0.5038(18) 0.026(3) Uiso 0.09 1 d D U P C 2
C104 C 0.2912(10) 0.5749(19) 0.5610(15) 0.016(3) Uiso 0.09 1 d DG U P C 2
C105 C 0.2197(11) 0.5661(19) 0.5477(16) 0.015(2) Uiso 0.09 1 d DG U P C 2
C106 C 0.1741(8) 0.6139(17) 0.6093(17) 0.027(4) Uiso 0.09 1 d G U P C 2
H106 H 0.125199 0.607812 0.600238 0.032 Uiso 0.09 1 calc R U P C 2
C107 C 0.1999(12) 0.6706(13) 0.6842(14) 0.030(4) Uiso 0.09 1 d G U P C 2
H107 H 0.168643 0.703249 0.726278 0.036 Uiso 0.09 1 calc R U P C 2
C108 C 0.2714(13) 0.6794(12) 0.6974(12) 0.021(3) Uiso 0.09 1 d G U P C 2
H108 H 0.288991 0.718184 0.748611 0.025 Uiso 0.09 1 calc R U P C 2
C109 C 0.3170(9) 0.6316(16) 0.6358(15) 0.020(4) Uiso 0.09 1 d G U P C 2
H109 H 0.365897 0.637681 0.644903 0.024 Uiso 0.09 1 calc R U P C 2
C110 C 0.1140(13) 0.4917(16) 0.3368(17) 0.030(3) Uiso 0.09 1 d D U P C 2
H11C H 0.136249 0.468596 0.276560 0.036 Uiso 0.09 1 calc R U P C 2
H11D H 0.069894 0.524847 0.320144 0.036 Uiso 0.09 1 calc R U P C 2
C111 C 0.1005(13) 0.4077(17) 0.4048(19) 0.033(3) Uiso 0.09 1 d D U P C 2
H11E H 0.119388 0.346816 0.377566 0.040 Uiso 0.09 1 calc R U P C 2
H11F H 0.049852 0.399507 0.415567 0.040 Uiso 0.09 1 calc R U P C 2
C112 C 0.3487(8) 0.4442(12) 0.3361(11) 0.035(3) Uiso 0.09 1 d DG U P C 2
C113 C 0.4072(9) 0.4903(10) 0.2988(13) 0.036(3) Uiso 0.09 1 d G U P C 2
H113 H 0.421088 0.551534 0.323568 0.043 Uiso 0.09 1 calc R U P C 2
C114 C 0.4453(7) 0.4469(11) 0.2252(12) 0.036(3) Uiso 0.09 1 d DG U P C 2
H114 H 0.485250 0.478385 0.199749 0.044 Uiso 0.09 1 calc R U P C 2
C115 C 0.4249(7) 0.3573(10) 0.1890(9) 0.036(3) Uiso 0.09 1 d DG U P C 2
C116 C 0.3664(8) 0.3112(9) 0.2263(12) 0.036(3) Uiso 0.09 1 d DG U P C 2
H116 H 0.352486 0.249968 0.201475 0.043 Uiso 0.09 1 calc R U P C 2
C117 C 0.3283(7) 0.3546(12) 0.2998(12) 0.036(4) Uiso 0.09 1 d G U P C 2
H117 H 0.288323 0.323116 0.325295 0.043 Uiso 0.09 1 calc R U P C 2
N115 N 0.4663(9) 0.3156(13) 0.1121(12) 0.033(3) Uiso 0.09 1 d D U P C 2
O115 O 0.4338(12) 0.2454(16) 0.1041(19) 0.038(3) Uiso 0.09 1 d D U P C 2
O116 O 0.5154(9) 0.3552(13) 0.0822(14) 0.041(3) Uiso 0.09 1 d D U P C 2
C118 C 0.3674(8) 0.4323(10) 0.5592(13) 0.028(3) Uiso 0.09 1 d G U P C 2
C119 C 0.4363(8) 0.4044(13) 0.5457(14) 0.028(3) Uiso 0.09 1 d G U P C 2
H119 H 0.466361 0.442662 0.506713 0.034 Uiso 0.09 1 calc R U P C 2
C120 C 0.4613(7) 0.3206(14) 0.5893(17) 0.021(4) Uiso 0.09 1 d G U P C 2
H120 H 0.508337 0.301490 0.580105 0.025 Uiso 0.09 1 calc R U P C 2
C121 C 0.4173(8) 0.2646(11) 0.6464(15) 0.030(3) Uiso 0.09 1 d G U P C 2
H121 H 0.434335 0.207308 0.676155 0.036 Uiso 0.09 1 calc R U P C 2
C122 C 0.3484(8) 0.2925(11) 0.6598(13) 0.028(3) Uiso 0.09 1 d G U P C 2
H122 H 0.318357 0.254298 0.698813 0.033 Uiso 0.09 1 calc R U P C 2
C123 C 0.3235(6) 0.3764(12) 0.6162(14) 0.029(3) Uiso 0.09 1 d G U P C 2
H123 H 0.276380 0.395470 0.625422 0.034 Uiso 0.09 1 calc R U P C 2
C131 C 0.3096(9) 1.0078(13) 0.7210(14) 0.014(4) Uiso 0.09 1 d D U P D 2
O131 O 0.2590(8) 0.9484(13) 0.6805(14) 0.020(3) Uiso 0.09 1 d D U P D 2
O132 O 0.3607(12) 0.9423(17) 0.7567(18) 0.016(7) Uiso 0.09 1 d D . P D 2
C132 C 0.1946(12) 1.002(3) 0.6638(16) 0.016(4) Uiso 0.09 1 d D U P D 2
H132 H 0.207903 1.065396 0.634048 0.019 Uiso 0.09 1 calc R U P D 2
O133 O 0.3400(8) 1.0659(11) 0.6514(12) 0.022(3) Uiso 0.09 1 d D U P D 2
C133 C 0.1621(9) 1.0241(13) 0.7604(12) 0.017(3) Uiso 0.09 1 d D U P D 2
H133 H 0.122098 1.068883 0.748184 0.021 Uiso 0.09 1 calc R U P D 2
C134 C 0.2133(8) 1.0783(13) 0.8216(13) 0.020(3) Uiso 0.09 1 d DG U P D 2
C135 C 0.2843(9) 1.0651(15) 0.8072(13) 0.016(4) Uiso 0.09 1 d DG U P D 2
C136 C 0.3321(7) 1.1107(15) 0.8674(14) 0.022(4) Uiso 0.09 1 d G U P D 2
H136 H 0.380589 1.101629 0.857534 0.026 Uiso 0.09 1 calc R U P D 2
C137 C 0.3088(8) 1.1696(12) 0.9422(12) 0.025(3) Uiso 0.09 1 d G U P D 2
H137 H 0.341368 1.200803 0.983372 0.030 Uiso 0.09 1 calc R U P D 2
C138 C 0.2377(9) 1.1829(14) 0.9567(13) 0.027(3) Uiso 0.09 1 d G U P D 2
H138 H 0.221821 1.223137 1.007753 0.032 Uiso 0.09 1 calc R U P D 2
C139 C 0.1900(7) 1.1372(15) 0.8964(15) 0.025(4) Uiso 0.09 1 d G U P D 2
H139 H 0.141494 1.146297 0.906296 0.029 Uiso 0.09 1 calc R U P D 2
C140 C 0.4001(12) 0.9201(16) 0.6622(18) 0.027(5) Uiso 0.09 1 d D . P D 2
H14A H 0.450358 0.910399 0.675161 0.032 Uiso 0.09 1 calc R U P D 2
H14B H 0.381380 0.860821 0.631419 0.032 Uiso 0.09 1 calc R U P D 2
C141 C 0.3893(14) 1.0061(19) 0.598(2) 0.041(7) Uiso 0.09 1 d D . P D 2
H14C H 0.433619 1.041223 0.587395 0.049 Uiso 0.09 1 calc R U P D 2
H14D H 0.369843 0.986404 0.534969 0.049 Uiso 0.09 1 calc R U P D 2
C142 C 0.1518(8) 0.9488(12) 0.5911(11) 0.027(3) Uiso 0.09 1 d DG U P D 2
C143 C 0.0918(9) 0.9929(10) 0.5558(13) 0.026(3) Uiso 0.09 1 d G U P D 2
H143 H 0.077137 1.053463 0.581289 0.031 Uiso 0.09 1 calc R U P D 2
C144 C 0.0534(7) 0.9484(11) 0.4832(13) 0.024(2) Uiso 0.09 1 d G U P D 2
H144 H 0.012458 0.978506 0.459069 0.028 Uiso 0.09 1 calc R U P D 2
C145 C 0.0749(7) 0.8598(10) 0.4459(11) 0.026(3) Uiso 0.09 1 d DG U P D 2
C146 C 0.1348(8) 0.8157(9) 0.4811(12) 0.027(3) Uiso 0.09 1 d G U P D 2
H146 H 0.149545 0.755107 0.455645 0.032 Uiso 0.09 1 calc R U P D 2
C147 C 0.1733(7) 0.8602(11) 0.5538(11) 0.024(2) Uiso 0.09 1 d G U P D 2
H147 H 0.214224 0.830062 0.577864 0.029 Uiso 0.09 1 calc R U P D 2
N145 N 0.0346(11) 0.8147(15) 0.3712(18) 0.028(3) Uiso 0.09 1 d D U P D 2
O145 O -0.0172(8) 0.8562(12) 0.3417(13) 0.028(2) Uiso 0.09 1 d D U P D 2
O146 O 0.0579(9) 0.7396(12) 0.3419(15) 0.029(2) Uiso 0.09 1 d D U P D 2
C148 C 0.1321(7) 0.9328(9) 0.8115(11) 0.017(3) Uiso 0.09 1 d DG U P D 2
C149 C 0.1752(6) 0.8760(10) 0.8690(12) 0.017(4) Uiso 0.09 1 d G . P D 2
H149 H 0.222498 0.893866 0.878254 0.020 Uiso 0.09 1 calc R U P D 2
C150 C 0.1490(8) 0.7931(10) 0.9130(12) 0.017(6) Uiso 0.09 1 d G . P D 2
H150 H 0.178399 0.754320 0.952337 0.021 Uiso 0.09 1 calc R U P D 2
C151 C 0.0797(9) 0.7671(11) 0.8995(16) 0.033(6) Uiso 0.09 1 d G . P D 2
H151 H 0.061810 0.710405 0.929581 0.040 Uiso 0.09 1 calc R U P D 2
C152 C 0.0367(7) 0.8239(13) 0.8420(17) 0.022(4) Uiso 0.09 1 d G U P D 2
H152 H -0.010681 0.806036 0.832742 0.026 Uiso 0.09 1 calc R U P D 2
C153 C 0.0628(7) 0.9068(11) 0.7980(13) 0.018(4) Uiso 0.09 1 d G . P D 2
H153 H 0.033416 0.945583 0.758658 0.022 Uiso 0.09 1 calc R U P D 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.399(2) . ?
C1 O1 1.400(3) . ?
C1 O2 1.408(3) . ?
C1 C5 1.503(3) . ?
O1 C2 1.437(3) . ?
C2 C12 1.507(3) . ?
C2 C3 1.548(3) . ?
C2 H2 1.0000 . ?
O2 C10 1.441(3) . ?
C3 C4 1.518(3) . ?
C3 C18 1.526(3) . ?
C3 H3 1.0000 . ?
O3 C11 1.440(3) . ?
C4 C9 1.393(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.396(3) . ?
C12 C13 1.396(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 N15 1.461(3) . ?
N15 O15 1.228(3) . ?
N15 O16 1.233(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 C23 1.391(3) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.367(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.407(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C31 O33 1.394(3) . ?
C31 O32 1.408(3) . ?
C31 O31 1.410(3) . ?
C31 C35 1.505(4) . ?
O31 C32 1.437(2) . ?
C32 C42 1.508(3) . ?
C32 C33 1.544(3) . ?
C32 H32 1.0000 . ?
O32 C40 1.440(3) . ?
C33 C34 1.522(3) . ?
C33 C48 1.530(4) . ?
C33 H33 1.0000 . ?
O33 C41 1.441(3) . ?
C34 C39 1.392(3) . ?
C34 C35 1.398(3) . ?
C35 C36 1.396(3) . ?
C36 C37 1.383(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.397(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.384(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.522(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.399(3) . ?
C42 C47 1.399(3) . ?
C43 C44 1.381(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.382(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.380(3) . ?
C45 N45 1.469(3) . ?
N45 O45 1.227(3) . ?
N45 O46 1.233(3) . ?
C46 C47 1.386(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C53 1.385(4) . ?
C48 C49 1.391(4) . ?
C49 C50 1.389(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.385(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.389(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.393(3) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C101 O102 1.40(2) . ?
C101 O103 1.43(2) . ?
C101 O101 1.47(2) . ?
C101 C105 1.560(19) . ?
O101 C102 1.420(14) . ?
C102 C112 1.492(18) . ?
C102 C103 1.52(2) . ?
C102 H10C 1.0000 . ?
O102 C110 1.452(14) . ?
C103 C104 1.44(2) . ?
C103 C118 1.53(3) . ?
C103 H103 1.0000 . ?
O103 C111 1.60(3) . ?
C104 C105 1.3900 . ?
C104 C109 1.3900 . ?
C105 C106 1.3900 . ?
C106 C107 1.3900 . ?
C106 H106 0.9500 . ?
C107 C108 1.3900 . ?
C107 H107 0.9500 . ?
C108 C109 1.3900 . ?
C108 H108 0.9500 . ?
C109 H109 0.9500 . ?
C110 C111 1.52(2) . ?
C110 H11C 0.9900 . ?
C110 H11D 0.9900 . ?
C111 H11E 0.9900 . ?
C111 H11F 0.9900 . ?
C112 C113 1.3900 . ?
C112 C117 1.3900 . ?
C113 C114 1.3900 . ?
C113 H113 0.9500 . ?
C114 C115 1.3900 . ?
C114 H114 0.9500 . ?
C115 C116 1.3900 . ?
C115 N115 1.448(16) . ?
C116 C117 1.3900 . ?
C116 H116 0.9500 . ?
C117 H117 0.9500 . ?
N115 O115 1.16(2) . ?
N115 O116 1.165(19) . ?
C118 C119 1.3900 . ?
C118 C123 1.3900 . ?
C119 C120 1.3900 . ?
C119 H119 0.9500 . ?
C120 C121 1.3900 . ?
C120 H120 0.9500 . ?
C121 C122 1.3900 . ?
C121 H121 0.9500 . ?
C122 C123 1.3900 . ?
C122 H122 0.9500 . ?
C123 H123 0.9500 . ?
C131 O133 1.38(2) . ?
C131 O131 1.39(2) . ?
C131 O132 1.42(2) . ?
C131 C135 1.511(18) . ?
O131 C132 1.46(3) . ?
O132 C140 1.54(3) . ?
C132 C142 1.493(18) . ?
C132 C133 1.51(2) . ?
C132 H132 1.0000 . ?
O133 C141 1.46(3) . ?
C133 C134 1.498(18) . ?
C133 C148 1.555(18) . ?
C133 H133 1.0000 . ?
C134 C135 1.3900 . ?
C134 C139 1.3900 . ?
C135 C136 1.3900 . ?
C136 C137 1.3900 . ?
C136 H136 0.9500 . ?
C137 C138 1.3900 . ?
C137 H137 0.9500 . ?
C138 C139 1.3900 . ?
C138 H138 0.9500 . ?
C139 H139 0.9500 . ?
C140 C141 1.50(2) . ?
C140 H14A 0.9900 . ?
C140 H14B 0.9900 . ?
C141 H14C 0.9900 . ?
C141 H14D 0.9900 . ?
C142 C143 1.3900 . ?
C142 C147 1.3900 . ?
C143 C144 1.3900 . ?
C143 H143 0.9500 . ?
C144 C145 1.3900 . ?
C144 H144 0.9500 . ?
C145 C146 1.3900 . ?
C145 N145 1.43(2) . ?
C146 C147 1.3900 . ?
C146 H146 0.9500 . ?
C147 H147 0.9500 . ?
N145 O146 1.20(2) . ?
N145 O145 1.22(2) . ?
C148 C149 1.3900 . ?
C148 C153 1.3900 . ?
C149 C150 1.3900 . ?
C149 H149 0.9500 . ?
C150 C151 1.3900 . ?
C150 H150 0.9500 . ?
C151 C152 1.3900 . ?
C151 H151 0.9500 . ?
C152 C153 1.3900 . ?
C152 H152 0.9500 . ?
C153 H153 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O1 105.88(17) . . ?
O3 C1 O2 105.81(16) . . ?
O1 C1 O2 110.37(19) . . ?
O3 C1 C5 112.73(19) . . ?
O1 C1 C5 112.80(18) . . ?
O2 C1 C5 109.01(18) . . ?
C1 O1 C2 111.72(17) . . ?
O1 C2 C12 108.46(17) . . ?
O1 C2 C3 108.30(17) . . ?
C12 C2 C3 115.40(16) . . ?
O1 C2 H2 108.2 . . ?
C12 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C1 O2 C10 106.40(16) . . ?
C4 C3 C18 111.9(2) . . ?
C4 C3 C2 107.57(17) . . ?
C18 C3 C2 112.96(17) . . ?
C4 C3 H3 108.1 . . ?
C18 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C1 O3 C11 105.17(16) . . ?
C9 C4 C5 119.4(2) . . ?
C9 C4 C3 121.2(2) . . ?
C5 C4 C3 119.5(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C1 118.4(2) . . ?
C4 C5 C1 121.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
O2 C10 C11 104.02(19) . . ?
O2 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
O2 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
O3 C11 C10 104.53(17) . . ?
O3 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
O3 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C17 C12 C13 119.25(19) . . ?
C17 C12 C2 121.21(19) . . ?
C13 C12 C2 119.48(18) . . ?
C14 C13 C12 121.02(19) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.96(18) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 122.68(19) . . ?
C16 C15 N15 119.22(19) . . ?
C14 C15 N15 118.09(19) . . ?
O15 N15 O16 123.2(2) . . ?
O15 N15 C15 118.3(2) . . ?
O16 N15 C15 118.47(19) . . ?
C15 C16 C17 118.72(19) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 120.38(19) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 118.7(2) . . ?
C19 C18 C3 121.4(2) . . ?
C23 C18 C3 119.9(2) . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.2(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
O33 C31 O32 106.14(19) . . ?
O33 C31 O31 106.1(2) . . ?
O32 C31 O31 110.2(2) . . ?
O33 C31 C35 112.3(2) . . ?
O32 C31 C35 109.3(2) . . ?
O31 C31 C35 112.6(2) . . ?
C31 O31 C32 111.70(16) . . ?
O31 C32 C42 108.90(16) . . ?
O31 C32 C33 107.61(17) . . ?
C42 C32 C33 116.42(17) . . ?
O31 C32 H32 107.9 . . ?
C42 C32 H32 107.9 . . ?
C33 C32 H32 107.9 . . ?
C31 O32 C40 106.57(17) . . ?
C34 C33 C48 110.6(2) . . ?
C34 C33 C32 107.37(19) . . ?
C48 C33 C32 114.12(19) . . ?
C34 C33 H33 108.2 . . ?
C48 C33 H33 108.2 . . ?
C32 C33 H33 108.2 . . ?
C31 O33 C41 105.10(18) . . ?
C39 C34 C35 119.2(2) . . ?
C39 C34 C33 120.7(2) . . ?
C35 C34 C33 120.0(2) . . ?
C36 C35 C34 119.8(2) . . ?
C36 C35 C31 119.1(2) . . ?
C34 C35 C31 121.2(2) . . ?
C37 C36 C35 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 119.8(2) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C39 C38 C37 119.7(2) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C34 121.0(2) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
O32 C40 C41 104.5(2) . . ?
O32 C40 H40A 110.9 . . ?
C41 C40 H40A 110.9 . . ?
O32 C40 H40B 110.9 . . ?
C41 C40 H40B 110.9 . . ?
H40A C40 H40B 108.9 . . ?
O33 C41 C40 103.95(18) . . ?
O33 C41 H41A 111.0 . . ?
C40 C41 H41A 111.0 . . ?
O33 C41 H41B 111.0 . . ?
C40 C41 H41B 111.0 . . ?
H41A C41 H41B 109.0 . . ?
C43 C42 C47 118.7(2) . . ?
C43 C42 C32 119.53(19) . . ?
C47 C42 C32 121.53(19) . . ?
C44 C43 C42 121.0(2) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 118.5(2) . . ?
C43 C44 H44 120.7 . . ?
C45 C44 H44 120.7 . . ?
C46 C45 C44 122.5(2) . . ?
C46 C45 N45 119.0(2) . . ?
C44 C45 N45 118.5(2) . . ?
O45 N45 O46 123.1(2) . . ?
O45 N45 C45 118.2(2) . . ?
O46 N45 C45 118.7(2) . . ?
C45 C46 C47 118.5(2) . . ?
C45 C46 H46 120.8 . . ?
C47 C46 H46 120.8 . . ?
C46 C47 C42 120.8(2) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
C53 C48 C49 119.2(3) . . ?
C53 C48 C33 120.0(3) . . ?
C49 C48 C33 120.7(2) . . ?
C50 C49 C48 120.5(2) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C51 C50 C49 120.3(2) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C52 119.3(2) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
C51 C52 C53 120.5(2) . . ?
C51 C52 H52 119.8 . . ?
C53 C52 H52 119.8 . . ?
C48 C53 C52 120.2(2) . . ?
C48 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
O102 C101 O103 114.1(16) . . ?
O102 C101 O101 103(2) . . ?
O103 C101 O101 103.9(18) . . ?
O102 C101 C105 114.4(18) . . ?
O103 C101 C105 111.5(19) . . ?
O101 C101 C105 108.5(16) . . ?
C102 O101 C101 112.1(17) . . ?
O101 C102 C112 109.3(18) . . ?
O101 C102 C103 107.0(17) . . ?
C112 C102 C103 113.0(17) . . ?
O101 C102 H10C 109.2 . . ?
C112 C102 H10C 109.2 . . ?
C103 C102 H10C 109.2 . . ?
C101 O102 C110 105.7(16) . . ?
C104 C103 C102 109.9(17) . . ?
C104 C103 C118 110.7(18) . . ?
C102 C103 C118 120.2(18) . . ?
C104 C103 H103 104.9 . . ?
C102 C103 H103 104.9 . . ?
C118 C103 H103 104.9 . . ?
C101 O103 C111 97.6(16) . . ?
C105 C104 C109 120.0 . . ?
C105 C104 C103 118.2(17) . . ?
C109 C104 C103 121.5(17) . . ?
C106 C105 C104 120.0 . . ?
C106 C105 C101 116.7(16) . . ?
C104 C105 C101 123.3(16) . . ?
C105 C106 C107 120.0 . . ?
C105 C106 H106 120.0 . . ?
C107 C106 H106 120.0 . . ?
C108 C107 C106 120.0 . . ?
C108 C107 H107 120.0 . . ?
C106 C107 H107 120.0 . . ?
C107 C108 C109 120.0 . . ?
C107 C108 H108 120.0 . . ?
C109 C108 H108 120.0 . . ?
C108 C109 C104 120.0 . . ?
C108 C109 H109 120.0 . . ?
C104 C109 H109 120.0 . . ?
O102 C110 C111 105.9(17) . . ?
O102 C110 H11C 110.6 . . ?
C111 C110 H11C 110.6 . . ?
O102 C110 H11D 110.6 . . ?
C111 C110 H11D 110.6 . . ?
H11C C110 H11D 108.7 . . ?
C110 C111 O103 106.3(15) . . ?
C110 C111 H11E 110.5 . . ?
O103 C111 H11E 110.5 . . ?
C110 C111 H11F 110.5 . . ?
O103 C111 H11F 110.5 . . ?
H11E C111 H11F 108.7 . . ?
C113 C112 C117 120.0 . . ?
C113 C112 C102 118.6(13) . . ?
C117 C112 C102 120.8(13) . . ?
C114 C113 C112 120.0 . . ?
C114 C113 H113 120.0 . . ?
C112 C113 H113 120.0 . . ?
C115 C114 C113 120.0 . . ?
C115 C114 H114 120.0 . . ?
C113 C114 H114 120.0 . . ?
C114 C115 C116 120.0 . . ?
C114 C115 N115 117.6(10) . . ?
C116 C115 N115 122.4(10) . . ?
C115 C116 C117 120.0 . . ?
C115 C116 H116 120.0 . . ?
C117 C116 H116 120.0 . . ?
C116 C117 C112 120.0 . . ?
C116 C117 H117 120.0 . . ?
C112 C117 H117 120.0 . . ?
O115 N115 O116 143(2) . . ?
O115 N115 C115 96.1(19) . . ?
O116 N115 C115 121.3(18) . . ?
C119 C118 C123 120.0 . . ?
C119 C118 C103 120.4(13) . . ?
C123 C118 C103 119.1(13) . . ?
C118 C119 C120 120.0 . . ?
C118 C119 H119 120.0 . . ?
C120 C119 H119 120.0 . . ?
C121 C120 C119 120.0 . . ?
C121 C120 H120 120.0 . . ?
C119 C120 H120 120.0 . . ?
C120 C121 C122 120.0 . . ?
C120 C121 H121 120.0 . . ?
C122 C121 H121 120.0 . . ?
C123 C122 C121 120.0 . . ?
C123 C122 H122 120.0 . . ?
C121 C122 H122 120.0 . . ?
C122 C123 C118 120.0 . . ?
C122 C123 H123 120.0 . . ?
C118 C123 H123 120.0 . . ?
O133 C131 O131 110.9(16) . . ?
O133 C131 O132 108.6(16) . . ?
O131 C131 O132 104.4(17) . . ?
O133 C131 C135 112.5(16) . . ?
O131 C131 C135 113.8(15) . . ?
O132 C131 C135 106.2(18) . . ?
C131 O131 C132 110.9(17) . . ?
C131 O132 C140 99.7(17) . . ?
O131 C132 C142 109(2) . . ?
O131 C132 C133 108.2(18) . . ?
C142 C132 C133 118.0(18) . . ?
O131 C132 H132 107.0 . . ?
C142 C132 H132 107.0 . . ?
C133 C132 H132 107.0 . . ?
C131 O133 C141 107.4(14) . . ?
C134 C133 C132 109.4(14) . . ?
C134 C133 C148 113.0(14) . . ?
C132 C133 C148 113.1(18) . . ?
C134 C133 H133 107.0 . . ?
C132 C133 H133 107.0 . . ?
C148 C133 H133 107.0 . . ?
C135 C134 C139 120.0 . . ?
C135 C134 C133 119.8(13) . . ?
C139 C134 C133 120.1(13) . . ?
C136 C135 C134 120.0 . . ?
C136 C135 C131 120.0(12) . . ?
C134 C135 C131 119.8(12) . . ?
C135 C136 C137 120.0 . . ?
C135 C136 H136 120.0 . . ?
C137 C136 H136 120.0 . . ?
C138 C137 C136 120.0 . . ?
C138 C137 H137 120.0 . . ?
C136 C137 H137 120.0 . . ?
C139 C138 C137 120.0 . . ?
C139 C138 H138 120.0 . . ?
C137 C138 H138 120.0 . . ?
C138 C139 C134 120.0 . . ?
C138 C139 H139 120.0 . . ?
C134 C139 H139 120.0 . . ?
C141 C140 O132 106.1(16) . . ?
C141 C140 H14A 110.5 . . ?
O132 C140 H14A 110.5 . . ?
C141 C140 H14B 110.5 . . ?
O132 C140 H14B 110.5 . . ?
H14A C140 H14B 108.7 . . ?
O133 C141 C140 103.9(16) . . ?
O133 C141 H14C 111.0 . . ?
C140 C141 H14C 111.0 . . ?
O133 C141 H14D 111.0 . . ?
C140 C141 H14D 111.0 . . ?
H14C C141 H14D 109.0 . . ?
C143 C142 C147 120.0 . . ?
C143 C142 C132 118.6(16) . . ?
C147 C142 C132 121.3(16) . . ?
C142 C143 C144 120.0 . . ?
C142 C143 H143 120.0 . . ?
C144 C143 H143 120.0 . . ?
C143 C144 C145 120.0 . . ?
C143 C144 H144 120.0 . . ?
C145 C144 H144 120.0 . . ?
C146 C145 C144 120.0 . . ?
C146 C145 N145 120.7(12) . . ?
C144 C145 N145 119.3(12) . . ?
C147 C146 C145 120.0 . . ?
C147 C146 H146 120.0 . . ?
C145 C146 H146 120.0 . . ?
C146 C147 C142 120.0 . . ?
C146 C147 H147 120.0 . . ?
C142 C147 H147 120.0 . . ?
O146 N145 O145 127(2) . . ?
O146 N145 C145 114.6(18) . . ?
O145 N145 C145 118.6(18) . . ?
C149 C148 C153 120.0 . . ?
C149 C148 C133 119.8(11) . . ?
C153 C148 C133 120.2(11) . . ?
C148 C149 C150 120.0 . . ?
C148 C149 H149 120.0 . . ?
C150 C149 H149 120.0 . . ?
C151 C150 C149 120.0 . . ?
C151 C150 H150 120.0 . . ?
C149 C150 H150 120.0 . . ?
C152 C151 C150 120.0 . . ?
C152 C151 H151 120.0 . . ?
C150 C151 H151 120.0 . . ?
C151 C152 C153 120.0 . . ?
C151 C152 H152 120.0 . . ?
C153 C152 H152 120.0 . . ?
C152 C153 C148 120.0 . . ?
C152 C153 H153 120.0 . . ?
C148 C153 H153 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 O1 C2 171.70(17) . . . . ?
O2 C1 O1 C2 -74.2(2) . . . . ?
C5 C1 O1 C2 48.0(3) . . . . ?
C1 O1 C2 C12 161.94(18) . . . . ?
C1 O1 C2 C3 -72.1(2) . . . . ?
O3 C1 O2 C10 35.2(2) . . . . ?
O1 C1 O2 C10 -79.0(2) . . . . ?
C5 C1 O2 C10 156.63(19) . . . . ?
O1 C2 C3 C4 56.8(2) . . . . ?
C12 C2 C3 C4 178.52(18) . . . . ?
O1 C2 C3 C18 -67.2(2) . . . . ?
C12 C2 C3 C18 54.5(2) . . . . ?
O1 C1 O3 C11 79.0(2) . . . . ?
O2 C1 O3 C11 -38.2(2) . . . . ?
C5 C1 O3 C11 -157.21(18) . . . . ?
C18 C3 C4 C9 -80.0(3) . . . . ?
C2 C3 C4 C9 155.3(2) . . . . ?
C18 C3 C4 C5 100.2(2) . . . . ?
C2 C3 C4 C5 -24.5(3) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C9 C4 C5 C1 -176.3(3) . . . . ?
C3 C4 C5 C1 3.5(3) . . . . ?
O3 C1 C5 C6 49.7(3) . . . . ?
O1 C1 C5 C6 169.5(2) . . . . ?
O2 C1 C5 C6 -67.5(3) . . . . ?
O3 C1 C5 C4 -133.5(2) . . . . ?
O1 C1 C5 C4 -13.6(3) . . . . ?
O2 C1 C5 C4 109.4(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C1 C5 C6 C7 177.0(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 179.6(2) . . . . ?
C1 O2 C10 C11 -17.8(2) . . . . ?
C1 O3 C11 C10 25.8(2) . . . . ?
O2 C10 C11 O3 -4.8(2) . . . . ?
O1 C2 C12 C17 2.8(3) . . . . ?
C3 C2 C12 C17 -118.9(2) . . . . ?
O1 C2 C12 C13 -174.48(18) . . . . ?
C3 C2 C12 C13 63.9(2) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C2 C12 C13 C14 176.57(18) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C13 C14 C15 N15 -179.21(19) . . . . ?
C16 C15 N15 O15 -178.9(2) . . . . ?
C14 C15 N15 O15 -0.2(3) . . . . ?
C16 C15 N15 O16 0.0(3) . . . . ?
C14 C15 N15 O16 178.71(19) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
N15 C15 C16 C17 178.96(19) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C2 C12 C17 C16 -176.78(19) . . . . ?
C4 C3 C18 C19 -36.6(3) . . . . ?
C2 C3 C18 C19 85.0(3) . . . . ?
C4 C3 C18 C23 145.5(2) . . . . ?
C2 C3 C18 C23 -92.9(2) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?
C3 C18 C19 C20 -177.4(2) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C20 C21 C22 C23 -1.5(4) . . . . ?
C21 C22 C23 C18 1.4(4) . . . . ?
C19 C18 C23 C22 -0.9(4) . . . . ?
C3 C18 C23 C22 177.0(2) . . . . ?
O33 C31 O31 C32 -171.34(17) . . . . ?
O32 C31 O31 C32 74.2(2) . . . . ?
C35 C31 O31 C32 -48.1(3) . . . . ?
C31 O31 C32 C42 -159.93(18) . . . . ?
C31 O31 C32 C33 73.0(2) . . . . ?
O33 C31 O32 C40 -32.5(3) . . . . ?
O31 C31 O32 C40 81.9(2) . . . . ?
C35 C31 O32 C40 -153.85(19) . . . . ?
O31 C32 C33 C34 -57.3(2) . . . . ?
C42 C32 C33 C34 -179.84(17) . . . . ?
O31 C32 C33 C48 65.7(2) . . . . ?
C42 C32 C33 C48 -56.8(3) . . . . ?
O32 C31 O33 C41 38.4(2) . . . . ?
O31 C31 O33 C41 -78.8(2) . . . . ?
C35 C31 O33 C41 157.8(2) . . . . ?
C48 C33 C34 C39 77.6(3) . . . . ?
C32 C33 C34 C39 -157.3(2) . . . . ?
C48 C33 C34 C35 -100.8(3) . . . . ?
C32 C33 C34 C35 24.3(3) . . . . ?
C39 C34 C35 C36 0.9(3) . . . . ?
C33 C34 C35 C36 179.2(2) . . . . ?
C39 C34 C35 C31 179.3(2) . . . . ?
C33 C34 C35 C31 -2.3(3) . . . . ?
O33 C31 C35 C36 -49.4(3) . . . . ?
O32 C31 C35 C36 68.1(3) . . . . ?
O31 C31 C35 C36 -169.09(19) . . . . ?
O33 C31 C35 C34 132.2(2) . . . . ?
O32 C31 C35 C34 -110.3(2) . . . . ?
O31 C31 C35 C34 12.5(3) . . . . ?
C34 C35 C36 C37 -1.0(3) . . . . ?
C31 C35 C36 C37 -179.4(2) . . . . ?
C35 C36 C37 C38 0.4(3) . . . . ?
C36 C37 C38 C39 0.2(3) . . . . ?
C37 C38 C39 C34 -0.3(3) . . . . ?
C35 C34 C39 C38 -0.2(3) . . . . ?
C33 C34 C39 C38 -178.6(2) . . . . ?
C31 O32 C40 C41 13.7(3) . . . . ?
C31 O33 C41 C40 -28.5(2) . . . . ?
O32 C40 C41 O33 8.9(2) . . . . ?
O31 C32 C42 C43 175.84(18) . . . . ?
C33 C32 C42 C43 -62.3(3) . . . . ?
O31 C32 C42 C47 1.0(3) . . . . ?
C33 C32 C42 C47 122.8(2) . . . . ?
C47 C42 C43 C44 1.1(3) . . . . ?
C32 C42 C43 C44 -173.87(19) . . . . ?
C42 C43 C44 C45 -0.6(3) . . . . ?
C43 C44 C45 C46 -0.6(3) . . . . ?
C43 C44 C45 N45 177.31(19) . . . . ?
C46 C45 N45 O45 -178.7(2) . . . . ?
C44 C45 N45 O45 3.3(3) . . . . ?
C46 C45 N45 O46 2.5(3) . . . . ?
C44 C45 N45 O46 -175.5(2) . . . . ?
C44 C45 C46 C47 1.1(3) . . . . ?
N45 C45 C46 C47 -176.7(2) . . . . ?
C45 C46 C47 C42 -0.6(3) . . . . ?
C43 C42 C47 C46 -0.5(3) . . . . ?
C32 C42 C47 C46 174.4(2) . . . . ?
C34 C33 C48 C53 -142.3(3) . . . . ?
C32 C33 C48 C53 96.5(3) . . . . ?
C34 C33 C48 C49 35.4(3) . . . . ?
C32 C33 C48 C49 -85.8(3) . . . . ?
C53 C48 C49 C50 0.9(4) . . . . ?
C33 C48 C49 C50 -176.8(2) . . . . ?
C48 C49 C50 C51 0.4(3) . . . . ?
C49 C50 C51 C52 -1.4(3) . . . . ?
C50 C51 C52 C53 1.1(4) . . . . ?
C49 C48 C53 C52 -1.2(4) . . . . ?
C33 C48 C53 C52 176.5(2) . . . . ?
C51 C52 C53 C48 0.2(4) . . . . ?
O102 C101 O101 C102 77(2) . . . . ?
O103 C101 O101 C102 -163(2) . . . . ?
C105 C101 O101 C102 -44(3) . . . . ?
C101 O101 C102 C112 -165(2) . . . . ?
C101 O101 C102 C103 72(3) . . . . ?
O103 C101 O102 C110 -33(3) . . . . ?
O101 C101 O102 C110 79(2) . . . . ?
C105 C101 O102 C110 -163.0(19) . . . . ?
O101 C102 C103 C104 -63(3) . . . . ?
C112 C102 C103 C104 177(2) . . . . ?
O101 C102 C103 C118 67(2) . . . . ?
C112 C102 C103 C118 -53(2) . . . . ?
O102 C101 O103 C111 33(2) . . . . ?
O101 C101 O103 C111 -79(2) . . . . ?
C105 C101 O103 C111 164.4(18) . . . . ?
C102 C103 C104 C105 30(2) . . . . ?
C118 C103 C104 C105 -105.0(17) . . . . ?
C102 C103 C104 C109 -155.6(17) . . . . ?
C118 C103 C104 C109 69(2) . . . . ?
C109 C104 C105 C106 0.0 . . . . ?
C103 C104 C105 C106 174(2) . . . . ?
C109 C104 C105 C101 -180(2) . . . . ?
C103 C104 C105 C101 -5(2) . . . . ?
O102 C101 C105 C106 76(2) . . . . ?
O103 C101 C105 C106 -55(2) . . . . ?
O101 C101 C105 C106 -169.0(17) . . . . ?
O102 C101 C105 C104 -104(2) . . . . ?
O103 C101 C105 C104 124.6(18) . . . . ?
O101 C101 C105 C104 11(3) . . . . ?
C104 C105 C106 C107 0.0 . . . . ?
C101 C105 C106 C107 180(2) . . . . ?
C105 C106 C107 C108 0.0 . . . . ?
C106 C107 C108 C109 0.0 . . . . ?
C107 C108 C109 C104 0.0 . . . . ?
C105 C104 C109 C108 0.0 . . . . ?
C103 C104 C109 C108 -174(2) . . . . ?
C101 O102 C110 C111 15(3) . . . . ?
O102 C110 C111 O103 4(3) . . . . ?
C101 O103 C111 C110 -21(2) . . . . ?
O101 C102 C112 C113 171.1(16) . . . . ?
C103 C102 C112 C113 -70(2) . . . . ?
O101 C102 C112 C117 0(3) . . . . ?
C103 C102 C112 C117 119.4(17) . . . . ?
C117 C112 C113 C114 0.0 . . . . ?
C102 C112 C113 C114 -170.8(15) . . . . ?
C112 C113 C114 C115 0.0 . . . . ?
C113 C114 C115 C116 0.0 . . . . ?
C113 C114 C115 N115 179.7(4) . . . . ?
C114 C115 C116 C117 0.0 . . . . ?
N115 C115 C116 C117 -179.7(4) . . . . ?
C115 C116 C117 C112 0.0 . . . . ?
C113 C112 C117 C116 0.0 . . . . ?
C102 C112 C117 C116 170.6(16) . . . . ?
C114 C115 N115 O115 179.6(5) . . . . ?
C116 C115 N115 O115 -0.7(8) . . . . ?
C114 C115 N115 O116 0.7(10) . . . . ?
C116 C115 N115 O116 -179.6(7) . . . . ?
C104 C103 C118 C119 -141.0(17) . . . . ?
C102 C103 C118 C119 89(2) . . . . ?
C104 C103 C118 C123 47(2) . . . . ?
C102 C103 C118 C123 -83.0(19) . . . . ?
C123 C118 C119 C120 0.0 . . . . ?
C103 C118 C119 C120 -172.1(17) . . . . ?
C118 C119 C120 C121 0.0 . . . . ?
C119 C120 C121 C122 0.0 . . . . ?
C120 C121 C122 C123 0.0 . . . . ?
C121 C122 C123 C118 0.0 . . . . ?
C119 C118 C123 C122 0.0 . . . . ?
C103 C118 C123 C122 172.2(17) . . . . ?
O133 C131 O131 C132 -78(2) . . . . ?
O132 C131 O131 C132 164.7(19) . . . . ?
C135 C131 O131 C132 49(2) . . . . ?
O133 C131 O132 C140 -38(2) . . . . ?
O131 C131 O132 C140 80(2) . . . . ?
C135 C131 O132 C140 -159.0(17) . . . . ?
C131 O131 C132 C142 160.3(19) . . . . ?
C131 O131 C132 C133 -70(2) . . . . ?
O131 C131 O133 C141 -78(2) . . . . ?
O132 C131 O133 C141 36(2) . . . . ?
C135 C131 O133 C141 153.7(18) . . . . ?
O131 C132 C133 C134 56(3) . . . . ?
C142 C132 C133 C134 -179(2) . . . . ?
O131 C132 C133 C148 -71(2) . . . . ?
C142 C132 C133 C148 54(3) . . . . ?
C132 C133 C134 C135 -28(2) . . . . ?
C148 C133 C134 C135 99.3(16) . . . . ?
C132 C133 C134 C139 156.1(19) . . . . ?
C148 C133 C134 C139 -76.9(18) . . . . ?
C139 C134 C135 C136 0.0 . . . . ?
C133 C134 C135 C136 -176.2(17) . . . . ?
C139 C134 C135 C131 -175(2) . . . . ?
C133 C134 C135 C131 9(2) . . . . ?
O133 C131 C135 C136 -66.9(19) . . . . ?
O131 C131 C135 C136 166.0(14) . . . . ?
O132 C131 C135 C136 52(2) . . . . ?
O133 C131 C135 C134 108.0(17) . . . . ?
O131 C131 C135 C134 -19(2) . . . . ?
O132 C131 C135 C134 -133.3(17) . . . . ?
C134 C135 C136 C137 0.0 . . . . ?
C131 C135 C136 C137 175(2) . . . . ?
C135 C136 C137 C138 0.0 . . . . ?
C136 C137 C138 C139 0.0 . . . . ?
C137 C138 C139 C134 0.0 . . . . ?
C135 C134 C139 C138 0.0 . . . . ?
C133 C134 C139 C138 176.2(17) . . . . ?
C131 O132 C140 C141 26(3) . . . . ?
C131 O133 C141 C140 -17(3) . . . . ?
O132 C140 C141 O133 -6(3) . . . . ?
O131 C132 C142 C143 -172.5(15) . . . . ?
C133 C132 C142 C143 64(3) . . . . ?
O131 C132 C142 C147 3(3) . . . . ?
C133 C132 C142 C147 -121(2) . . . . ?
C147 C142 C143 C144 0.0 . . . . ?
C132 C142 C143 C144 175.5(19) . . . . ?
C142 C143 C144 C145 0.0 . . . . ?
C143 C144 C145 C146 0.0 . . . . ?
C143 C144 C145 N145 179.8(18) . . . . ?
C144 C145 C146 C147 0.0 . . . . ?
N145 C145 C146 C147 -179.8(19) . . . . ?
C145 C146 C147 C142 0.0 . . . . ?
C143 C142 C147 C146 0.0 . . . . ?
C132 C142 C147 C146 -175(2) . . . . ?
C146 C145 N145 O146 -2(3) . . . . ?
C144 C145 N145 O146 178.4(18) . . . . ?
C146 C145 N145 O145 -179.3(19) . . . . ?
C144 C145 N145 O145 1(3) . . . . ?
C134 C133 C148 C149 -38.3(18) . . . . ?
C132 C133 C148 C149 86.6(17) . . . . ?
C134 C133 C148 C153 143.2(14) . . . . ?
C132 C133 C148 C153 -91.9(17) . . . . ?
C153 C148 C149 C150 0.0 . . . . ?
C133 C148 C149 C150 -178.5(15) . . . . ?
C148 C149 C150 C151 0.0 . . . . ?
C149 C150 C151 C152 0.0 . . . . ?
C150 C151 C152 C153 0.0 . . . . ?
C151 C152 C153 C148 0.0 . . . . ?
C149 C148 C153 C152 0.0 . . . . ?
C133 C148 C153 C152 178.5(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3^a H3^a O15^a 1.00 2.60 3.412(3) 138.8 2_565 yes
C33^a H33^a O45^a 1.00 2.59 3.432(3) 142.2 2_675 yes
C46^a H46^a O2^a 0.95 2.52 3.441(3) 162.4 . yes
C133^b H133^b O145^b 1.00 2.61 3.42(2) 138.9 2_575 yes

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.049

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF3084CUFMI
_database_code_depnum_ccdc_archive 'CCDC 2145030'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_JF3084CUFMI         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.942 Why?
RESPONSE: Data were mistakenly only collected to 0.86A resoltion for Cu here. There is a second data collection of the same crystal that is collected with Mo radiation to 0.59A resolution.  This is the reference structure for handedness.
;
# Added during the CSD deposition process: Friday 28 January 2022 12:15 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N O7'
_chemical_formula_sum            'C31 H29 N O7'
_chemical_formula_weight         527.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.0296(3)
_cell_length_b                   13.7412(3)
_cell_length_c                   17.5524(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2660.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      4.74
_cell_measurement_theta_max      63.20
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.707
_exptl_crystal_size_mid          0.516
_exptl_crystal_size_min          0.458
_exptl_absorpt_coefficient_mu    0.768
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.720
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7365
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9689
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.735
_diffrn_reflns_theta_max         63.039
_diffrn_reflns_theta_full        63.039
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             3957
_reflns_number_gt                3954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.887

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences.

 
 Data were mistakenly only collected to 0.86A resolution and 
 integrated to 0.83A.  Structure provides solid evidence of the
 correct hand being chosen. This rendition of the structure is
 being published in the CCDC as a reference structure for the exact
 same crystal collected with Mo radiation and integrated to 0.69A
 resolution.
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1637 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3957
_refine_ls_number_parameters     387
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.69689(15) 0.30668(12) 0.34624(11) 0.0195(4) Uani 1 1 d . . . . .
H1 H 0.737446 0.364251 0.322463 0.016(5) Uiso 1 1 calc R . . . .
C2 C 0.77033(16) 0.21423(13) 0.32807(10) 0.0211(4) Uani 1 1 d . . . . .
O2 O 0.88695(11) 0.21851(9) 0.36175(7) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.77990(16) 0.20051(13) 0.24253(11) 0.0219(4) Uani 1 1 d . . . . .
O3 O 0.70928(11) 0.13254(9) 0.36157(8) 0.0233(3) Uani 1 1 d D . . . .
C4 C 0.69040(16) 0.23740(13) 0.19398(11) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.58406(16) 0.29838(13) 0.22258(10) 0.0208(4) Uani 1 1 d . . . . .
H5 H 0.601211 0.367681 0.208933 0.021(5) Uiso 1 1 calc R . . . .
C6 C 0.57206(15) 0.29313(13) 0.31081(10) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.539861 0.227702 0.325389 0.020(5) Uiso 1 1 calc R . . . .
C7 C 0.8937(2) 0.14540(16) 0.41974(13) 0.0348(5) Uani 1 1 d D . . . .
H7A H 0.874413 0.172790 0.470479 0.046(7) Uiso 1 1 calc R . . A 1
H7B H 0.975234 0.115307 0.421416 0.055(8) Uiso 1 1 calc R . . A 1
C8 C 0.7999(2) 0.07353(17) 0.39526(16) 0.0285(5) Uani 0.84 1 d D U P B 1
H8A H 0.833610 0.026777 0.357920 0.033(7) Uiso 0.84 1 calc R . P B 1
H8B H 0.767393 0.037133 0.439424 0.037(7) Uiso 0.84 1 calc R . P B 1
C8B C 0.7721(10) 0.1017(10) 0.4310(7) 0.031(2) Uiso 0.16 1 d D U P B 2
H8B1 H 0.776741 0.029909 0.434553 0.037 Uiso 0.16 1 calc R U P B 2
H8B2 H 0.732136 0.127729 0.477152 0.037 Uiso 0.16 1 calc R U P B 2
C9 C 0.87726(17) 0.14838(14) 0.21249(11) 0.0262(4) Uani 1 1 d . . . . .
H9 H 0.938224 0.124012 0.245626 0.024(5) Uiso 1 1 calc R . . . .
C10 C 0.88602(18) 0.13175(14) 0.13483(12) 0.0305(5) Uani 1 1 d . . . . .
H10 H 0.951941 0.095277 0.114877 0.032(6) Uiso 1 1 calc R . . . .
C11 C 0.79858(19) 0.16840(15) 0.08677(12) 0.0319(5) Uani 1 1 d . . . . .
H11 H 0.804679 0.157666 0.033441 0.037(6) Uiso 1 1 calc R . . . .
C12 C 0.70159(17) 0.22094(15) 0.11581(11) 0.0269(4) Uani 1 1 d . . . . .
H12 H 0.642000 0.246057 0.082036 0.022(5) Uiso 1 1 calc R . . . .
C13 C 0.68959(16) 0.32140(12) 0.43138(11) 0.0197(4) Uani 1 1 d . . . . .
N13 N 0.78267(13) 0.37229(10) 0.46768(9) 0.0202(3) Uani 1 1 d . . . . .
O13 O 0.60862(11) 0.28743(9) 0.47006(7) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.87192(16) 0.43182(13) 0.43590(11) 0.0206(4) Uani 1 1 d . . . . .
O14 O 0.88095(11) 0.46006(9) 0.37130(7) 0.0234(3) Uani 1 1 d . . . . .
C15 C 0.91902(18) 0.40815(15) 0.56106(12) 0.0275(5) Uani 1 1 d . . . . .
H15A H 0.930890 0.450324 0.606176 0.036(6) Uiso 1 1 calc R . . . .
H15B H 0.969437 0.348988 0.566721 0.032(6) Uiso 1 1 calc R . . . .
O15 O 0.94869(11) 0.45988(10) 0.49108(8) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.78556(17) 0.38188(13) 0.55093(10) 0.0223(4) Uani 1 1 d . . . . .
H16 H 0.767225 0.318082 0.575804 0.024(5) Uiso 1 1 calc R . . . .
C17 C 0.69995(17) 0.46032(13) 0.57963(11) 0.0222(4) Uani 1 1 d . . . . .
C18 C 0.68170(19) 0.46824(16) 0.65806(12) 0.0306(5) Uani 1 1 d . . . . .
H18 H 0.720383 0.423915 0.691744 0.044(7) Uiso 1 1 calc R . . . .
C19 C 0.6072(2) 0.54069(18) 0.68691(12) 0.0364(5) Uani 1 1 d . . . . .
H19 H 0.594560 0.545375 0.740316 0.047(7) Uiso 1 1 calc R . . . .
C20 C 0.55142(19) 0.60594(15) 0.63872(13) 0.0343(5) Uani 1 1 d . . . . .
H20 H 0.501770 0.656209 0.658895 0.038(6) Uiso 1 1 calc R . . . .
C21 C 0.56793(19) 0.59801(15) 0.56101(13) 0.0310(5) Uani 1 1 d . . . . .
H21 H 0.528480 0.642212 0.527582 0.038(6) Uiso 1 1 calc R . . . .
C22 C 0.64226(18) 0.52536(13) 0.53157(11) 0.0240(4) Uani 1 1 d . . . . .
H22 H 0.653506 0.520365 0.478057 0.028(6) Uiso 1 1 calc R . . . .
C23 C 0.46439(17) 0.27109(14) 0.18590(10) 0.0219(4) Uani 1 1 d . . . . .
C24 C 0.42660(17) 0.17389(14) 0.18576(11) 0.0238(4) Uani 1 1 d . . . . .
H24 H 0.479147 0.125129 0.205302 0.026(5) Uiso 1 1 calc R . . . .
C25 C 0.31418(18) 0.14752(15) 0.15769(11) 0.0279(4) Uani 1 1 d . . . . .
H25 H 0.289741 0.081233 0.158506 0.033(6) Uiso 1 1 calc R . . . .
C26 C 0.23737(18) 0.21767(16) 0.12844(11) 0.0312(5) Uani 1 1 d . . . . .
H26 H 0.159892 0.199936 0.109288 0.032(6) Uiso 1 1 calc R . . . .
C27 C 0.27420(19) 0.31393(16) 0.12726(12) 0.0330(5) Uani 1 1 d . . . . .
H27 H 0.221910 0.362249 0.106805 0.042(7) Uiso 1 1 calc R . . . .
C28 C 0.38707(18) 0.34057(14) 0.15575(11) 0.0278(4) Uani 1 1 d . . . . .
H28 H 0.411319 0.406887 0.154530 0.047(7) Uiso 1 1 calc R . . . .
C29 C 0.48383(17) 0.37044(13) 0.33667(11) 0.0222(4) Uani 1 1 d . . . . .
O29 O 0.51203(13) 0.45467(9) 0.34688(9) 0.0333(3) Uani 1 1 d . . . . .
C30 C 0.27588(18) 0.40859(15) 0.35254(13) 0.0335(5) Uani 1 1 d . . . . .
H30A H 0.285222 0.460914 0.314216 0.039(6) Uiso 1 1 calc R . . . .
H30B H 0.279653 0.438064 0.403955 0.039(6) Uiso 1 1 calc R . . . .
O30 O 0.37175(11) 0.33611(9) 0.34358(8) 0.0252(3) Uani 1 1 d . . . . .
C31 C 0.15729(19) 0.35707(18) 0.34159(15) 0.0431(6) Uani 1 1 d . . . . .
H31A H 0.146068 0.309205 0.382383 0.075(10) Uiso 1 1 calc R . . . .
H31B H 0.157300 0.323810 0.292204 0.081(11) Uiso 1 1 calc R . . . .
H31C H 0.090993 0.404516 0.343044 0.053(7) Uiso 1 1 calc R . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.510(3) . ?
C1 C6 1.522(2) . ?
C1 C2 1.540(2) . ?
C1 H1 1.0000 . ?
C2 O2 1.417(2) . ?
C2 O3 1.435(2) . ?
C2 C3 1.517(3) . ?
O2 C7 1.432(3) . ?
C3 C9 1.394(3) . ?
C3 C4 1.399(3) . ?
O3 C8 1.417(3) . ?
O3 C8B 1.464(10) . ?
C4 C12 1.396(3) . ?
C4 C5 1.526(3) . ?
C5 C23 1.516(3) . ?
C5 C6 1.556(3) . ?
C5 H5 1.0000 . ?
C6 C29 1.510(2) . ?
C6 H6 1.0000 . ?
C7 C8B 1.482(10) . ?
C7 C8 1.493(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O13 1.215(2) . ?
C13 N13 1.396(2) . ?
N13 C14 1.396(2) . ?
N13 C16 1.468(2) . ?
C14 O14 1.203(2) . ?
C14 O15 1.343(2) . ?
C15 O15 1.456(2) . ?
C15 C16 1.526(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H16 1.0000 . ?
C17 C22 1.384(3) . ?
C17 C18 1.395(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.385(3) . ?
C23 C24 1.399(3) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O29 1.212(2) . ?
C29 O30 1.329(2) . ?
C30 O30 1.461(2) . ?
C30 C31 1.500(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C1 C6 111.87(14) . . ?
C13 C1 C2 110.08(14) . . ?
C6 C1 C2 106.87(14) . . ?
C13 C1 H1 109.3 . . ?
C6 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
O2 C2 O3 106.71(14) . . ?
O2 C2 C3 110.79(15) . . ?
O3 C2 C3 109.94(14) . . ?
O2 C2 C1 110.91(14) . . ?
O3 C2 C1 108.28(13) . . ?
C3 C2 C1 110.12(15) . . ?
C2 O2 C7 108.35(14) . . ?
C9 C3 C4 119.94(18) . . ?
C9 C3 C2 119.45(17) . . ?
C4 C3 C2 120.59(16) . . ?
C8 O3 C2 106.70(15) . . ?
C2 O3 C8B 110.2(4) . . ?
C12 C4 C3 118.53(17) . . ?
C12 C4 C5 118.69(17) . . ?
C3 C4 C5 122.73(16) . . ?
C23 C5 C4 113.18(15) . . ?
C23 C5 C6 109.71(14) . . ?
C4 C5 C6 111.55(15) . . ?
C23 C5 H5 107.4 . . ?
C4 C5 H5 107.4 . . ?
C6 C5 H5 107.4 . . ?
C29 C6 C1 111.96(14) . . ?
C29 C6 C5 108.75(14) . . ?
C1 C6 C5 108.91(14) . . ?
C29 C6 H6 109.1 . . ?
C1 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
O2 C7 C8B 109.3(4) . . ?
O2 C7 C8 102.90(16) . . ?
O2 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
O2 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
O3 C8 C7 103.33(17) . . ?
O3 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
O3 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
O3 C8B C7 101.6(6) . . ?
O3 C8B H8B1 111.5 . . ?
C7 C8B H8B1 111.5 . . ?
O3 C8B H8B2 111.5 . . ?
C7 C8B H8B2 111.5 . . ?
H8B1 C8B H8B2 109.3 . . ?
C10 C9 C3 120.70(19) . . ?
C10 C9 H9 119.7 . . ?
C3 C9 H9 119.7 . . ?
C11 C10 C9 119.58(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.35(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C4 120.90(19) . . ?
C11 C12 H12 119.6 . . ?
C4 C12 H12 119.6 . . ?
O13 C13 N13 118.55(16) . . ?
O13 C13 C1 122.73(16) . . ?
N13 C13 C1 118.65(15) . . ?
C13 N13 C14 129.02(15) . . ?
C13 N13 C16 121.03(15) . . ?
C14 N13 C16 109.26(14) . . ?
O14 C14 O15 122.36(17) . . ?
O14 C14 N13 128.61(17) . . ?
O15 C14 N13 108.94(16) . . ?
O15 C15 C16 103.53(15) . . ?
O15 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
O15 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C14 O15 C15 109.05(14) . . ?
N13 C16 C17 112.36(15) . . ?
N13 C16 C15 99.10(15) . . ?
C17 C16 C15 113.15(15) . . ?
N13 C16 H16 110.6 . . ?
C17 C16 H16 110.6 . . ?
C15 C16 H16 110.6 . . ?
C22 C17 C18 118.99(18) . . ?
C22 C17 C16 122.81(17) . . ?
C18 C17 C16 118.18(17) . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.52(19) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.76(19) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.53(18) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C28 C23 C24 118.29(17) . . ?
C28 C23 C5 121.86(17) . . ?
C24 C23 C5 119.76(16) . . ?
C25 C24 C23 121.20(18) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C24 119.95(18) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.48(18) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C28 120.60(19) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C23 C28 C27 120.47(18) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
O29 C29 O30 124.36(17) . . ?
O29 C29 C6 123.42(17) . . ?
O30 C29 C6 112.16(15) . . ?
O30 C30 C31 107.19(16) . . ?
O30 C30 H30A 110.3 . . ?
C31 C30 H30A 110.3 . . ?
O30 C30 H30B 110.3 . . ?
C31 C30 H30B 110.3 . . ?
H30A C30 H30B 108.5 . . ?
C29 O30 C30 116.18(14) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 O2 -55.84(18) . . . . ?
C6 C1 C2 O2 -177.53(14) . . . . ?
C13 C1 C2 O3 60.92(17) . . . . ?
C6 C1 C2 O3 -60.77(17) . . . . ?
C13 C1 C2 C3 -178.85(14) . . . . ?
C6 C1 C2 C3 59.47(18) . . . . ?
O3 C2 O2 C7 -4.71(18) . . . . ?
C3 C2 O2 C7 -124.37(16) . . . . ?
C1 C2 O2 C7 113.01(17) . . . . ?
O2 C2 C3 C9 31.4(2) . . . . ?
O3 C2 C3 C9 -86.27(19) . . . . ?
C1 C2 C3 C9 154.50(16) . . . . ?
O2 C2 C3 C4 -150.29(16) . . . . ?
O3 C2 C3 C4 92.01(19) . . . . ?
C1 C2 C3 C4 -27.2(2) . . . . ?
O2 C2 O3 C8 -17.7(2) . . . . ?
C3 C2 O3 C8 102.49(18) . . . . ?
C1 C2 O3 C8 -137.16(18) . . . . ?
O2 C2 O3 C8B 16.0(7) . . . . ?
C3 C2 O3 C8B 136.2(7) . . . . ?
C1 C2 O3 C8B -103.5(7) . . . . ?
C9 C3 C4 C12 -0.2(3) . . . . ?
C2 C3 C4 C12 -178.47(17) . . . . ?
C9 C3 C4 C5 -177.58(17) . . . . ?
C2 C3 C4 C5 4.2(3) . . . . ?
C12 C4 C5 C23 45.1(2) . . . . ?
C3 C4 C5 C23 -137.56(17) . . . . ?
C12 C4 C5 C6 169.36(16) . . . . ?
C3 C4 C5 C6 -13.3(2) . . . . ?
C13 C1 C6 C29 49.0(2) . . . . ?
C2 C1 C6 C29 169.51(15) . . . . ?
C13 C1 C6 C5 169.24(13) . . . . ?
C2 C1 C6 C5 -70.20(18) . . . . ?
C23 C5 C6 C29 -65.64(18) . . . . ?
C4 C5 C6 C29 168.13(14) . . . . ?
C23 C5 C6 C1 172.11(14) . . . . ?
C4 C5 C6 C1 45.89(19) . . . . ?
C2 O2 C7 C8B -7.9(7) . . . . ?
C2 O2 C7 C8 23.8(2) . . . . ?
C2 O3 C8 C7 32.0(2) . . . . ?
O2 C7 C8 O3 -34.0(2) . . . . ?
C2 O3 C8B C7 -19.8(10) . . . . ?
O2 C7 C8B O3 16.7(10) . . . . ?
C4 C3 C9 C10 -0.6(3) . . . . ?
C2 C3 C9 C10 177.68(17) . . . . ?
C3 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C4 -0.2(3) . . . . ?
C3 C4 C12 C11 0.6(3) . . . . ?
C5 C4 C12 C11 178.10(17) . . . . ?
C6 C1 C13 O13 28.7(2) . . . . ?
C2 C1 C13 O13 -89.98(19) . . . . ?
C6 C1 C13 N13 -154.38(15) . . . . ?
C2 C1 C13 N13 86.96(18) . . . . ?
O13 C13 N13 C14 -167.26(16) . . . . ?
C1 C13 N13 C14 15.7(3) . . . . ?
O13 C13 N13 C16 2.1(2) . . . . ?
C1 C13 N13 C16 -174.92(15) . . . . ?
C13 N13 C14 O14 8.2(3) . . . . ?
C16 N13 C14 O14 -162.18(18) . . . . ?
C13 N13 C14 O15 -175.16(16) . . . . ?
C16 N13 C14 O15 14.46(19) . . . . ?
O14 C14 O15 C15 -176.07(16) . . . . ?
N13 C14 O15 C15 7.04(19) . . . . ?
C16 C15 O15 C14 -24.47(19) . . . . ?
C13 N13 C16 C17 -79.4(2) . . . . ?
C14 N13 C16 C17 91.94(18) . . . . ?
C13 N13 C16 C15 160.89(15) . . . . ?
C14 N13 C16 C15 -27.83(18) . . . . ?
O15 C15 C16 N13 30.39(17) . . . . ?
O15 C15 C16 C17 -88.79(18) . . . . ?
N13 C16 C17 C22 -10.1(2) . . . . ?
C15 C16 C17 C22 101.1(2) . . . . ?
N13 C16 C17 C18 171.60(16) . . . . ?
C15 C16 C17 C18 -77.2(2) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C16 C17 C18 C19 178.03(18) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 1.2(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
C16 C17 C22 C21 -177.78(18) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C4 C5 C23 C28 -131.57(19) . . . . ?
C6 C5 C23 C28 103.1(2) . . . . ?
C4 C5 C23 C24 52.0(2) . . . . ?
C6 C5 C23 C24 -73.3(2) . . . . ?
C28 C23 C24 C25 -1.2(3) . . . . ?
C5 C23 C24 C25 175.32(17) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C24 C23 C28 C27 1.0(3) . . . . ?
C5 C23 C28 C27 -175.51(18) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C1 C6 C29 O29 37.4(3) . . . . ?
C5 C6 C29 O29 -83.0(2) . . . . ?
C1 C6 C29 O30 -145.35(16) . . . . ?
C5 C6 C29 O30 94.27(17) . . . . ?
O29 C29 O30 C30 9.7(3) . . . . ?
C6 C29 O30 C30 -167.55(16) . . . . ?
C31 C30 O30 C29 167.49(18) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034

_vrf_PLAT023_JF3084CUFMI         
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.58 Ang-1
RESPONSE:
Data were mistakenly only collected to 0.86A resoltion for Cu here but 
integrated/processed to 0.83A resolution.

Structure is correct.
;


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF3005FMI
_database_code_depnum_ccdc_archive 'CCDC 2087133'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C25 H25 N O7), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C52 H54 N2 O15'
_chemical_formula_weight         946.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7429(7)
_cell_length_b                   14.3116(10)
_cell_length_c                   18.0645(12)
_cell_angle_alpha                67.1270(15)
_cell_angle_beta                 81.5420(16)
_cell_angle_gamma                80.5606(17)
_cell_volume                     2279.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.64

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.577
_exptl_crystal_size_min          0.232
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8837
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28137
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         30.684
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             14103
_reflns_number_gt                12151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

JF3005  JMR-1-159-B

A colorless block with approximate orthogonal dimensions 0.284 x 0.453 x 0.460mm3 was placed and optically centered on the Bruker(1) Venture Dual source Kappa Photon100 diffractometer at â\/E?173Â°C(100K).  Indexing of the unit cell used a random set of reflections collected from three series of 0.5Â° wide omega-scans, 5 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Data were collected [MoKa] with 0.3Â° wide scans, variable time per frame dependent upon detector 2theta angle and varying Ï? and omega angles such that nearly all unique reflections were collected at least once.  The crystal to detector distance was 65.00mm, thus providing a complete sphere of data to 2thetamax=61.32Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7 with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint(1) and absorption using Blessingâ\/E?s method and merged as incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the probable space group and set up the initial files. System symmetry, lack of systematic absences and intensity statistics indicated the centrosymmetric triclinic space group P-1 (no. 2). The structure was determined by direct methods with the location of nearly all of the non-hydrogen atoms for the nearly identical two molecules of interest with the program XT(5). The structure was refined with XL(6). The 134093 data collected were merged for identical indices to 28137 reflections and then for least squares refinement to 14103 unique data [R(int)=0.0169]. An ethyl acetate molecule was found disordered lying upon itself and was therefore refined at half occupancy. Non-hydrogen atoms were refined anisotropically. Hydrogen atoms were idealized throughout the final refinement. The final structure was refined to convergence with R(F)=5.54%, wR(F2)=13.65%, GOF=1.037 for all 14103 unique reflections [R(F)=4.83, wR(F2)=12.97% for those 12151 data with Fo > 4sigma(Fo)]. The final difference-Fourier map was featureless indicating that the structure is both correct and complete. 

References:

1.	Bruker (2019) APEX3 (Version 2019.1) and (2016) SAINT (Version 8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.
2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193) for the Dual Source X-ray diffractometer.

J.C. Fettinger, 15Jan2021



;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.7117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0239(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         14103
_refine_ls_number_parameters     652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74456(10) 0.69401(7) 0.15580(6) 0.01751(17) Uani 1 1 d . . . . .
O1 O 0.61810(8) 0.76093(6) 0.13631(5) 0.01988(14) Uani 1 1 d . . . . .
C2 C 0.84610(10) 0.70469(7) 0.07968(6) 0.01793(17) Uani 1 1 d . . . . .
H2 H 0.800283 0.690725 0.039611 0.022 Uiso 1 1 calc R U . . .
O2 O 0.80872(8) 0.72610(6) 0.20723(5) 0.01971(14) Uani 1 1 d . . . . .
C3 C 0.97533(10) 0.62712(7) 0.10540(6) 0.01799(17) Uani 1 1 d . . . . .
H3 H 1.010299 0.635579 0.151509 0.022 Uiso 1 1 calc R U . . .
C4 C 0.93710(11) 0.51651(8) 0.13403(6) 0.01930(18) Uani 1 1 d . . . . .
H4 H 0.921651 0.504047 0.085280 0.023 Uiso 1 1 calc R U . . .
C5 C 0.80243(11) 0.50280(8) 0.18976(7) 0.0224(2) Uani 1 1 d . . . . .
C6 C 0.71163(11) 0.58463(8) 0.19962(6) 0.02004(18) Uani 1 1 d . . . . .
C7 C 0.59064(12) 0.56609(9) 0.25327(7) 0.0256(2) Uani 1 1 d . . . . .
H7 H 0.528989 0.621927 0.259331 0.031 Uiso 1 1 calc R U . . .
C8 C 0.56006(14) 0.46728(10) 0.29752(9) 0.0355(3) Uani 1 1 d . . . . .
H8 H 0.479294 0.455353 0.334898 0.043 Uiso 1 1 calc R U . . .
C9 C 0.64819(15) 0.38541(10) 0.28701(10) 0.0408(3) Uani 1 1 d . . . . .
H9 H 0.627115 0.317503 0.316778 0.049 Uiso 1 1 calc R U . . .
C10 C 0.76690(14) 0.40329(9) 0.23292(9) 0.0329(3) Uani 1 1 d . . . . .
H10 H 0.825140 0.347248 0.224936 0.039 Uiso 1 1 calc R U . . .
C11 C 0.60442(11) 0.83251(8) 0.17552(6) 0.02092(19) Uani 1 1 d . . . . .
H11A H 0.506582 0.844527 0.197169 0.025 Uiso 1 1 calc R U . . .
H11B H 0.635578 0.898525 0.137974 0.025 Uiso 1 1 calc R U . . .
C12 C 0.69933(11) 0.78013(8) 0.24295(6) 0.02098(19) Uani 1 1 d . . . . .
H12A H 0.736213 0.830414 0.257702 0.025 Uiso 1 1 calc R U . . .
H12B H 0.650152 0.732595 0.291458 0.025 Uiso 1 1 calc R U . . .
C13 C 0.88708(11) 0.81250(8) 0.04337(6) 0.01919(18) Uani 1 1 d . . . . .
N13 N 0.79262(9) 0.89163(7) -0.00021(5) 0.01987(17) Uani 1 1 d . . . . .
O13 O 0.99569(8) 0.83301(6) 0.05600(5) 0.02598(17) Uani 1 1 d . . . . .
C14 C 0.67905(11) 0.88637(8) -0.03693(6) 0.02160(19) Uani 1 1 d . . . . .
O14 O 0.64118(9) 0.81365(7) -0.04169(5) 0.02698(17) Uani 1 1 d . . . . .
C15 C 0.68216(13) 1.05604(9) -0.05740(8) 0.0298(2) Uani 1 1 d . . . . .
H15A H 0.620655 1.087173 -0.022289 0.036 Uiso 1 1 calc R U . . .
H15B H 0.706823 1.110882 -0.109470 0.036 Uiso 1 1 calc R U . . .
O15 O 0.61311(9) 0.98190(6) -0.07011(5) 0.02669(17) Uani 1 1 d . . . . .
C16 C 0.81340(12) 0.99709(8) -0.01702(7) 0.0229(2) Uani 1 1 d . . . . .
H16A H 0.898859 1.016606 -0.053673 0.027 Uiso 1 1 calc R U . . .
H16B H 0.819117 1.007957 0.033267 0.027 Uiso 1 1 calc R U . . .
C17 C 1.09137(11) 0.64376(8) 0.03723(6) 0.02068(19) Uani 1 1 d . . . . .
O17 O 1.07303(9) 0.66276(7) -0.03221(5) 0.02983(18) Uani 1 1 d . . . . .
C18 C 1.33719(12) 0.63421(10) 0.00523(8) 0.0298(2) Uani 1 1 d . . . . .
H18A H 1.339849 0.704194 -0.035886 0.036 Uiso 1 1 calc R U . . .
H18B H 1.332236 0.587233 -0.022328 0.036 Uiso 1 1 calc R U . . .
O18 O 1.21667(8) 0.63089(6) 0.06406(5) 0.02310(16) Uani 1 1 d . . . . .
C19 C 1.46542(13) 0.60197(12) 0.05085(9) 0.0353(3) Uani 1 1 d . . . . .
H19A H 1.470626 0.650294 0.076401 0.053 Uiso 1 1 calc R U . . .
H19B H 1.548913 0.601187 0.013410 0.053 Uiso 1 1 calc R U . . .
H19C H 1.460099 0.533473 0.092406 0.053 Uiso 1 1 calc R U . . .
C20 C 1.05981(11) 0.44140(8) 0.17289(6) 0.01990(18) Uani 1 1 d . . . . .
C21 C 1.15117(12) 0.39049(8) 0.13022(7) 0.0240(2) Uani 1 1 d . . . . .
H21 H 1.132936 0.398827 0.077637 0.029 Uiso 1 1 calc R U . . .
C22 C 1.26944(13) 0.32723(9) 0.16397(8) 0.0294(2) Uani 1 1 d . . . . .
H22 H 1.331626 0.293339 0.134185 0.035 Uiso 1 1 calc R U . . .
C23 C 1.29582(14) 0.31404(10) 0.24092(9) 0.0347(3) Uani 1 1 d . . . . .
H23 H 1.376705 0.271746 0.263734 0.042 Uiso 1 1 calc R U . . .
C24 C 1.20360(15) 0.36287(10) 0.28473(8) 0.0339(3) Uani 1 1 d . . . . .
H24 H 1.220694 0.352925 0.337871 0.041 Uiso 1 1 calc R U . . .
C25 C 1.08656(13) 0.42614(9) 0.25085(7) 0.0260(2) Uani 1 1 d . . . . .
H25 H 1.024110 0.459352 0.281036 0.031 Uiso 1 1 calc R U . . .
C31 C 0.17999(10) 0.78509(8) 0.31106(6) 0.01831(18) Uani 1 1 d . . . . .
O31 O 0.07160(8) 0.72294(6) 0.32546(5) 0.02222(15) Uani 1 1 d . . . . .
C32 C 0.24525(10) 0.76369(7) 0.38973(6) 0.01820(17) Uani 1 1 d . . . . .
H32 H 0.172449 0.780491 0.429282 0.022 Uiso 1 1 calc R U . . .
O32 O 0.28525(8) 0.75787(6) 0.25591(5) 0.02012(15) Uani 1 1 d . . . . .
C33 C 0.36094(10) 0.83298(7) 0.36806(6) 0.01775(17) Uani 1 1 d . . . . .
H33 H 0.421715 0.826283 0.320286 0.021 Uiso 1 1 calc R U . . .
C34 C 0.29400(10) 0.94525(7) 0.34556(6) 0.01827(17) Uani 1 1 d . . . . .
H34 H 0.243599 0.951514 0.396097 0.022 Uiso 1 1 calc R U . . .
C35 C 0.18506(10) 0.97228(8) 0.28555(6) 0.01932(18) Uani 1 1 d . . . . .
C36 C 0.12535(10) 0.89768(8) 0.27288(6) 0.01889(18) Uani 1 1 d . . . . .
C37 C 0.01997(11) 0.92682(9) 0.22050(7) 0.0237(2) Uani 1 1 d . . . . .
H37 H -0.020564 0.876137 0.212086 0.028 Uiso 1 1 calc R U . . .
C38 C -0.02565(12) 1.02967(10) 0.18071(7) 0.0276(2) Uani 1 1 d . . . . .
H38 H -0.097798 1.048913 0.145672 0.033 Uiso 1 1 calc R U . . .
C39 C 0.03400(12) 1.10418(9) 0.19210(7) 0.0278(2) Uani 1 1 d . . . . .
H39 H 0.004037 1.174408 0.164249 0.033 Uiso 1 1 calc R U . . .
C40 C 0.13797(12) 1.07538(8) 0.24457(7) 0.0248(2) Uani 1 1 d . . . . .
H40 H 0.177755 1.126532 0.252774 0.030 Uiso 1 1 calc R U . . .
C41 C 0.11944(11) 0.64819(8) 0.28967(7) 0.02198(19) Uani 1 1 d . . . . .
H41A H 0.041434 0.631353 0.269416 0.026 Uiso 1 1 calc R U . . .
H41B H 0.165025 0.584813 0.328717 0.026 Uiso 1 1 calc R U . . .
C42 C 0.22270(11) 0.70126(8) 0.22140(6) 0.02216(19) Uani 1 1 d . . . . .
H42A H 0.293066 0.651548 0.206695 0.027 Uiso 1 1 calc R U . . .
H42B H 0.175278 0.747350 0.173139 0.027 Uiso 1 1 calc R U . . .
C43 C 0.30543(11) 0.65265(8) 0.42602(6) 0.02011(18) Uani 1 1 d . . . . .
N43 N 0.22410(10) 0.58213(7) 0.48344(6) 0.02157(17) Uani 1 1 d . . . . .
O43 O 0.42365(9) 0.62281(6) 0.40566(5) 0.02631(17) Uani 1 1 d . . . . .
C44 C 0.08955(12) 0.59768(8) 0.51964(6) 0.0237(2) Uani 1 1 d . . . . .
O44 O 0.01084(10) 0.67460(7) 0.50677(6) 0.0350(2) Uani 1 1 d . . . . .
C45 C 0.17657(13) 0.43076(9) 0.58624(8) 0.0294(2) Uani 1 1 d . . . . .
H45A H 0.150250 0.365260 0.589444 0.035 Uiso 1 1 calc R U . . .
H45B H 0.218233 0.419142 0.636329 0.035 Uiso 1 1 calc R U . . .
O45 O 0.05595(9) 0.50712(6) 0.57521(5) 0.02623(17) Uani 1 1 d . . . . .
C46 C 0.27799(13) 0.47335(8) 0.51329(8) 0.0291(2) Uani 1 1 d . . . . .
H46A H 0.374704 0.462264 0.528365 0.035 Uiso 1 1 calc R U . . .
H46B H 0.275315 0.442912 0.472874 0.035 Uiso 1 1 calc R U . . .
C47 C 0.45098(11) 0.80629(8) 0.43691(6) 0.02048(19) Uani 1 1 d . . . . .
O47 O 0.40664(9) 0.78531(7) 0.50673(5) 0.02829(18) Uani 1 1 d . . . . .
C48 C 0.68134(12) 0.81528(10) 0.46311(7) 0.0268(2) Uani 1 1 d . . . . .
H48A H 0.708430 0.745110 0.501139 0.032 Uiso 1 1 calc R U . . .
H48B H 0.637590 0.857514 0.494529 0.032 Uiso 1 1 calc R U . . .
O48 O 0.58529(8) 0.81432(7) 0.40898(5) 0.02367(16) Uani 1 1 d . . . . .
C49 C 0.80716(13) 0.86030(11) 0.40981(9) 0.0352(3) Uani 1 1 d . . . . .
H49A H 0.851998 0.815683 0.381345 0.053 Uiso 1 1 calc R U . . .
H49B H 0.873606 0.866458 0.442998 0.053 Uiso 1 1 calc R U . . .
H49C H 0.777643 0.927996 0.370434 0.053 Uiso 1 1 calc R U . . .
C50 C 0.40777(11) 1.01591(8) 0.31820(6) 0.01996(18) Uani 1 1 d . . . . .
C51 C 0.45375(12) 1.04815(8) 0.37316(7) 0.0231(2) Uani 1 1 d . . . . .
H51 H 0.407924 1.030701 0.426133 0.028 Uiso 1 1 calc R U . . .
C52 C 0.56595(13) 1.10556(9) 0.35121(8) 0.0274(2) Uani 1 1 d . . . . .
H52 H 0.596847 1.126405 0.389283 0.033 Uiso 1 1 calc R U . . .
C53 C 0.63263(12) 1.13230(9) 0.27360(8) 0.0289(2) Uani 1 1 d . . . . .
H53 H 0.709827 1.170787 0.258600 0.035 Uiso 1 1 calc R U . . .
C54 C 0.58577(12) 1.10244(9) 0.21807(7) 0.0267(2) Uani 1 1 d . . . . .
H54 H 0.630056 1.121813 0.164674 0.032 Uiso 1 1 calc R U . . .
C55 C 0.47443(11) 1.04436(8) 0.24004(7) 0.02203(19) Uani 1 1 d . . . . .
H55 H 0.443623 1.023968 0.201682 0.026 Uiso 1 1 calc R U . . .
C61 C 1.0864(3) 0.8464(2) 0.60366(17) 0.0327(5) Uani 0.5 1 d . . P A -1
H61A H 1.044618 0.786631 0.643156 0.049 Uiso 0.5 1 calc R U P A -1
H61B H 1.122357 0.882092 0.631987 0.049 Uiso 0.5 1 calc R U P A -1
H61C H 1.163175 0.824279 0.570338 0.049 Uiso 0.5 1 calc R U P A -1
O61 O 0.85589(19) 0.90659(16) 0.56015(12) 0.0344(4) Uani 0.5 1 d . . P A -1
C62 C 0.9781(3) 0.91680(19) 0.55108(15) 0.0271(4) Uani 0.5 1 d . . P A -1
O62 O 1.03277(18) 0.99625(19) 0.49180(14) 0.0347(4) Uani 0.5 1 d . . P A -1
C63 C 0.9374(3) 1.0696(2) 0.43522(18) 0.0405(6) Uani 0.5 1 d . . P A -1
H63A H 0.845882 1.081382 0.464252 0.049 Uiso 0.5 1 calc R U P A -1
H63B H 0.922456 1.043251 0.394191 0.049 Uiso 0.5 1 calc R U P A -1
C64 C 1.0021(6) 1.1666(3) 0.3958(2) 0.0538(10) Uani 0.5 1 d . . P A -1
H64A H 1.001464 1.198094 0.435315 0.081 Uiso 0.5 1 calc R U P A -1
H64B H 0.948746 1.213384 0.351086 0.081 Uiso 0.5 1 calc R U P A -1
H64C H 1.098633 1.152084 0.375133 0.081 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4274(11) . ?
C1 O2 1.4358(12) . ?
C1 C6 1.5189(14) . ?
C1 C2 1.5424(14) . ?
O1 C11 1.4354(13) . ?
C2 C13 1.5194(14) . ?
C2 C3 1.5317(14) . ?
C2 H2 1.0000 . ?
O2 C12 1.4372(12) . ?
C3 C17 1.5172(14) . ?
C3 C4 1.5533(14) . ?
C3 H3 1.0000 . ?
C4 C5 1.5217(15) . ?
C4 C20 1.5220(14) . ?
C4 H4 1.0000 . ?
C5 C6 1.4006(14) . ?
C5 C10 1.4054(15) . ?
C6 C7 1.4021(15) . ?
C7 C8 1.3845(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3933(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3886(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.5149(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O13 1.2178(13) . ?
C13 N13 1.3883(13) . ?
N13 C14 1.3971(14) . ?
N13 C16 1.4619(14) . ?
C14 O14 1.1964(14) . ?
C14 O15 1.3526(13) . ?
C15 O15 1.4491(15) . ?
C15 C16 1.5234(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.2101(14) . ?
C17 O18 1.3379(13) . ?
C18 O18 1.4569(13) . ?
C18 C19 1.5070(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3927(15) . ?
C20 C25 1.3960(15) . ?
C21 C22 1.3981(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3895(17) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 O31 1.4218(12) . ?
C31 O32 1.4373(12) . ?
C31 C36 1.5226(14) . ?
C31 C32 1.5432(14) . ?
O31 C41 1.4370(13) . ?
C32 C43 1.5154(14) . ?
C32 C33 1.5304(14) . ?
C32 H32 1.0000 . ?
O32 C42 1.4432(13) . ?
C33 C47 1.5180(14) . ?
C33 C34 1.5488(14) . ?
C33 H33 1.0000 . ?
C34 C50 1.5210(14) . ?
C34 C35 1.5261(14) . ?
C34 H34 1.0000 . ?
C35 C36 1.4013(14) . ?
C35 C40 1.4015(14) . ?
C36 C37 1.4007(14) . ?
C37 C38 1.3921(16) . ?
C37 H37 0.9500 . ?
C38 C39 1.3878(18) . ?
C38 H38 0.9500 . ?
C39 C40 1.3914(16) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.5058(15) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 O43 1.2168(13) . ?
C43 N43 1.3889(13) . ?
N43 C44 1.4003(14) . ?
N43 C46 1.4672(14) . ?
C44 O44 1.1960(14) . ?
C44 O45 1.3512(13) . ?
C45 O45 1.4468(14) . ?
C45 C46 1.5081(17) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 O47 1.2064(13) . ?
C47 O48 1.3380(13) . ?
C48 O48 1.4547(13) . ?
C48 C49 1.5082(18) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C55 1.3968(15) . ?
C50 C51 1.3979(15) . ?
C51 C52 1.3932(16) . ?
C51 H51 0.9500 . ?
C52 C53 1.3895(18) . ?
C52 H52 0.9500 . ?
C53 C54 1.3889(18) . ?
C53 H53 0.9500 . ?
C54 C55 1.3921(15) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C61 C62 1.494(4) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
O61 C62 1.203(3) . ?
C62 O62 1.345(3) . ?
O62 C63 1.461(4) . ?
C63 C64 1.489(5) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 106.15(7) . . ?
O1 C1 C6 109.81(8) . . ?
O2 C1 C6 110.50(8) . . ?
O1 C1 C2 111.27(8) . . ?
O2 C1 C2 107.89(8) . . ?
C6 C1 C2 111.10(8) . . ?
C1 O1 C11 109.09(7) . . ?
C13 C2 C3 110.15(8) . . ?
C13 C2 C1 108.75(8) . . ?
C3 C2 C1 107.81(8) . . ?
C13 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C1 C2 H2 110.0 . . ?
C1 O2 C12 106.77(7) . . ?
C17 C3 C2 111.56(8) . . ?
C17 C3 C4 109.43(8) . . ?
C2 C3 C4 110.44(8) . . ?
C17 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C5 C4 C20 112.62(9) . . ?
C5 C4 C3 111.30(8) . . ?
C20 C4 C3 109.24(8) . . ?
C5 C4 H4 107.8 . . ?
C20 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C6 C5 C10 118.42(10) . . ?
C6 C5 C4 123.17(9) . . ?
C10 C5 C4 118.41(10) . . ?
C5 C6 C7 120.03(10) . . ?
C5 C6 C1 121.21(9) . . ?
C7 C6 C1 118.71(9) . . ?
C8 C7 C6 120.70(11) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.75(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.85(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 121.18(11) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
O1 C11 C12 103.14(8) . . ?
O1 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
O1 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
O2 C12 C11 102.09(8) . . ?
O2 C12 H12A 111.4 . . ?
C11 C12 H12A 111.4 . . ?
O2 C12 H12B 111.4 . . ?
C11 C12 H12B 111.4 . . ?
H12A C12 H12B 109.2 . . ?
O13 C13 N13 118.69(9) . . ?
O13 C13 C2 122.20(9) . . ?
N13 C13 C2 118.89(9) . . ?
C13 N13 C14 128.60(9) . . ?
C13 N13 C16 119.32(9) . . ?
C14 N13 C16 111.94(8) . . ?
O14 C14 O15 122.52(10) . . ?
O14 C14 N13 129.26(10) . . ?
O15 C14 N13 108.21(9) . . ?
O15 C15 C16 105.84(9) . . ?
O15 C15 H15A 110.6 . . ?
C16 C15 H15A 110.6 . . ?
O15 C15 H15B 110.6 . . ?
C16 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
C14 O15 C15 111.36(9) . . ?
N13 C16 C15 101.80(9) . . ?
N13 C16 H16A 111.4 . . ?
C15 C16 H16A 111.4 . . ?
N13 C16 H16B 111.4 . . ?
C15 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?
O17 C17 O18 124.34(10) . . ?
O17 C17 C3 124.06(10) . . ?
O18 C17 C3 111.55(9) . . ?
O18 C18 C19 107.03(10) . . ?
O18 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O18 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
C17 O18 C18 116.23(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 118.78(10) . . ?
C21 C20 C4 120.82(9) . . ?
C25 C20 C4 120.32(9) . . ?
C20 C21 C22 120.66(11) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.91(11) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.88(11) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.08(12) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.67(11) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
O31 C31 O32 106.46(8) . . ?
O31 C31 C36 110.66(8) . . ?
O32 C31 C36 109.40(8) . . ?
O31 C31 C32 111.04(8) . . ?
O32 C31 C32 108.72(8) . . ?
C36 C31 C32 110.45(8) . . ?
C31 O31 C41 108.31(8) . . ?
C43 C32 C33 110.20(8) . . ?
C43 C32 C31 110.63(8) . . ?
C33 C32 C31 107.16(8) . . ?
C43 C32 H32 109.6 . . ?
C33 C32 H32 109.6 . . ?
C31 C32 H32 109.6 . . ?
C31 O32 C42 107.33(7) . . ?
C47 C33 C32 112.49(8) . . ?
C47 C33 C34 108.71(8) . . ?
C32 C33 C34 109.15(8) . . ?
C47 C33 H33 108.8 . . ?
C32 C33 H33 108.8 . . ?
C34 C33 H33 108.8 . . ?
C50 C34 C35 114.30(8) . . ?
C50 C34 C33 109.84(8) . . ?
C35 C34 C33 111.41(8) . . ?
C50 C34 H34 107.0 . . ?
C35 C34 H34 107.0 . . ?
C33 C34 H34 107.0 . . ?
C36 C35 C40 118.75(10) . . ?
C36 C35 C34 122.39(9) . . ?
C40 C35 C34 118.79(9) . . ?
C37 C36 C35 119.95(10) . . ?
C37 C36 C31 119.10(9) . . ?
C35 C36 C31 120.83(9) . . ?
C38 C37 C36 120.32(11) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C39 C38 C37 120.17(10) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 119.59(10) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C35 121.21(11) . . ?
C39 C40 H40 119.4 . . ?
C35 C40 H40 119.4 . . ?
O31 C41 C42 102.74(8) . . ?
O31 C41 H41A 111.2 . . ?
C42 C41 H41A 111.2 . . ?
O31 C41 H41B 111.2 . . ?
C42 C41 H41B 111.2 . . ?
H41A C41 H41B 109.1 . . ?
O32 C42 C41 101.85(8) . . ?
O32 C42 H42A 111.4 . . ?
C41 C42 H42A 111.4 . . ?
O32 C42 H42B 111.4 . . ?
C41 C42 H42B 111.4 . . ?
H42A C42 H42B 109.3 . . ?
O43 C43 N43 118.55(9) . . ?
O43 C43 C32 121.71(9) . . ?
N43 C43 C32 119.74(9) . . ?
C43 N43 C44 129.51(9) . . ?
C43 N43 C46 119.65(9) . . ?
C44 N43 C46 110.84(9) . . ?
O44 C44 O45 122.17(10) . . ?
O44 C44 N43 129.46(10) . . ?
O45 C44 N43 108.36(9) . . ?
O45 C45 C46 105.44(9) . . ?
O45 C45 H45A 110.7 . . ?
C46 C45 H45A 110.7 . . ?
O45 C45 H45B 110.7 . . ?
C46 C45 H45B 110.7 . . ?
H45A C45 H45B 108.8 . . ?
C44 O45 C45 110.28(9) . . ?
N43 C46 C45 101.44(9) . . ?
N43 C46 H46A 111.5 . . ?
C45 C46 H46A 111.5 . . ?
N43 C46 H46B 111.5 . . ?
C45 C46 H46B 111.5 . . ?
H46A C46 H46B 109.3 . . ?
O47 C47 O48 124.70(10) . . ?
O47 C47 C33 124.58(10) . . ?
O48 C47 C33 110.63(9) . . ?
O48 C48 C49 105.85(10) . . ?
O48 C48 H48A 110.6 . . ?
C49 C48 H48A 110.6 . . ?
O48 C48 H48B 110.6 . . ?
C49 C48 H48B 110.6 . . ?
H48A C48 H48B 108.7 . . ?
C47 O48 C48 117.97(9) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C55 C50 C51 118.72(10) . . ?
C55 C50 C34 121.20(9) . . ?
C51 C50 C34 119.95(9) . . ?
C52 C51 C50 120.81(11) . . ?
C52 C51 H51 119.6 . . ?
C50 C51 H51 119.6 . . ?
C53 C52 C51 119.95(11) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C54 C53 C52 119.63(11) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
C53 C54 C55 120.53(11) . . ?
C53 C54 H54 119.7 . . ?
C55 C54 H54 119.7 . . ?
C54 C55 C50 120.33(10) . . ?
C54 C55 H55 119.8 . . ?
C50 C55 H55 119.8 . . ?
C62 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C62 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O61 C62 O62 122.8(2) . . ?
O61 C62 C61 125.4(2) . . ?
O62 C62 C61 111.8(2) . . ?
C62 O62 C63 116.9(2) . . ?
O62 C63 C64 107.6(3) . . ?
O62 C63 H63A 110.2 . . ?
C64 C63 H63A 110.2 . . ?
O62 C63 H63B 110.2 . . ?
C64 C63 H63B 110.2 . . ?
H63A C63 H63B 108.5 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 C11 -0.34(10) . . . . ?
C6 C1 O1 C11 119.12(9) . . . . ?
C2 C1 O1 C11 -117.46(9) . . . . ?
O1 C1 C2 C13 63.18(10) . . . . ?
O2 C1 C2 C13 -52.87(10) . . . . ?
C6 C1 C2 C13 -174.14(8) . . . . ?
O1 C1 C2 C3 -177.41(8) . . . . ?
O2 C1 C2 C3 66.54(10) . . . . ?
C6 C1 C2 C3 -54.72(10) . . . . ?
O1 C1 O2 C12 22.74(10) . . . . ?
C6 C1 O2 C12 -96.26(9) . . . . ?
C2 C1 O2 C12 142.10(8) . . . . ?
C13 C2 C3 C17 -51.99(11) . . . . ?
C1 C2 C3 C17 -170.51(8) . . . . ?
C13 C2 C3 C4 -173.94(8) . . . . ?
C1 C2 C3 C4 67.54(10) . . . . ?
C17 C3 C4 C5 -168.26(8) . . . . ?
C2 C3 C4 C5 -45.07(11) . . . . ?
C17 C3 C4 C20 66.75(10) . . . . ?
C2 C3 C4 C20 -170.06(8) . . . . ?
C20 C4 C5 C6 135.37(11) . . . . ?
C3 C4 C5 C6 12.30(14) . . . . ?
C20 C4 C5 C10 -45.17(14) . . . . ?
C3 C4 C5 C10 -168.24(11) . . . . ?
C10 C5 C6 C7 1.79(17) . . . . ?
C4 C5 C6 C7 -178.75(10) . . . . ?
C10 C5 C6 C1 179.10(11) . . . . ?
C4 C5 C6 C1 -1.44(16) . . . . ?
O1 C1 C6 C5 146.52(10) . . . . ?
O2 C1 C6 C5 -96.73(11) . . . . ?
C2 C1 C6 C5 22.99(13) . . . . ?
O1 C1 C6 C7 -36.14(13) . . . . ?
O2 C1 C6 C7 80.62(12) . . . . ?
C2 C1 C6 C7 -159.66(10) . . . . ?
C5 C6 C7 C8 0.59(18) . . . . ?
C1 C6 C7 C8 -176.79(11) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C5 1.7(2) . . . . ?
C6 C5 C10 C9 -3.0(2) . . . . ?
C4 C5 C10 C9 177.55(13) . . . . ?
C1 O1 C11 C12 -20.61(10) . . . . ?
C1 O2 C12 C11 -34.67(10) . . . . ?
O1 C11 C12 O2 33.42(10) . . . . ?
C3 C2 C13 O13 -20.07(14) . . . . ?
C1 C2 C13 O13 97.87(11) . . . . ?
C3 C2 C13 N13 165.32(9) . . . . ?
C1 C2 C13 N13 -76.74(11) . . . . ?
O13 C13 N13 C14 164.46(10) . . . . ?
C2 C13 N13 C14 -20.74(16) . . . . ?
O13 C13 N13 C16 -10.91(15) . . . . ?
C2 C13 N13 C16 163.89(9) . . . . ?
C13 N13 C14 O14 -3.16(19) . . . . ?
C16 N13 C14 O14 172.48(11) . . . . ?
C13 N13 C14 O15 177.75(10) . . . . ?
C16 N13 C14 O15 -6.60(12) . . . . ?
O14 C14 O15 C15 -178.50(11) . . . . ?
N13 C14 O15 C15 0.66(12) . . . . ?
C16 C15 O15 C14 5.09(13) . . . . ?
C13 N13 C16 C15 -174.70(9) . . . . ?
C14 N13 C16 C15 9.20(12) . . . . ?
O15 C15 C16 N13 -8.27(12) . . . . ?
C2 C3 C17 O17 -42.28(14) . . . . ?
C4 C3 C17 O17 80.24(13) . . . . ?
C2 C3 C17 O18 140.13(9) . . . . ?
C4 C3 C17 O18 -97.35(10) . . . . ?
O17 C17 O18 C18 -3.94(16) . . . . ?
C3 C17 O18 C18 173.64(9) . . . . ?
C19 C18 O18 C17 -171.34(10) . . . . ?
C5 C4 C20 C21 135.63(10) . . . . ?
C3 C4 C20 C21 -100.15(11) . . . . ?
C5 C4 C20 C25 -47.49(13) . . . . ?
C3 C4 C20 C25 76.73(12) . . . . ?
C25 C20 C21 C22 -1.58(17) . . . . ?
C4 C20 C21 C22 175.35(10) . . . . ?
C20 C21 C22 C23 0.61(18) . . . . ?
C21 C22 C23 C24 0.8(2) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 C20 0.1(2) . . . . ?
C21 C20 C25 C24 1.22(18) . . . . ?
C4 C20 C25 C24 -175.72(11) . . . . ?
O32 C31 O31 C41 8.66(10) . . . . ?
C36 C31 O31 C41 127.45(9) . . . . ?
C32 C31 O31 C41 -109.52(9) . . . . ?
O31 C31 C32 C43 59.31(10) . . . . ?
O32 C31 C32 C43 -57.48(10) . . . . ?
C36 C31 C32 C43 -177.53(8) . . . . ?
O31 C31 C32 C33 179.47(8) . . . . ?
O32 C31 C32 C33 62.67(10) . . . . ?
C36 C31 C32 C33 -57.37(10) . . . . ?
O31 C31 O32 C42 15.37(10) . . . . ?
C36 C31 O32 C42 -104.24(9) . . . . ?
C32 C31 O32 C42 135.06(8) . . . . ?
C43 C32 C33 C47 -49.28(11) . . . . ?
C31 C32 C33 C47 -169.71(8) . . . . ?
C43 C32 C33 C34 -170.02(8) . . . . ?
C31 C32 C33 C34 69.54(10) . . . . ?
C47 C33 C34 C50 60.91(10) . . . . ?
C32 C33 C34 C50 -176.07(8) . . . . ?
C47 C33 C34 C35 -171.41(8) . . . . ?
C32 C33 C34 C35 -48.38(11) . . . . ?
C50 C34 C35 C36 143.12(10) . . . . ?
C33 C34 C35 C36 17.88(13) . . . . ?
C50 C34 C35 C40 -40.12(13) . . . . ?
C33 C34 C35 C40 -165.36(9) . . . . ?
C40 C35 C36 C37 -0.45(15) . . . . ?
C34 C35 C36 C37 176.31(9) . . . . ?
C40 C35 C36 C31 175.50(9) . . . . ?
C34 C35 C36 C31 -7.74(15) . . . . ?
O31 C31 C36 C37 -33.14(12) . . . . ?
O32 C31 C36 C37 83.85(11) . . . . ?
C32 C31 C36 C37 -156.51(9) . . . . ?
O31 C31 C36 C35 150.88(9) . . . . ?
O32 C31 C36 C35 -92.13(11) . . . . ?
C32 C31 C36 C35 27.51(12) . . . . ?
C35 C36 C37 C38 0.16(16) . . . . ?
C31 C36 C37 C38 -175.85(10) . . . . ?
C36 C37 C38 C39 0.62(17) . . . . ?
C37 C38 C39 C40 -1.09(18) . . . . ?
C38 C39 C40 C35 0.80(18) . . . . ?
C36 C35 C40 C39 -0.03(16) . . . . ?
C34 C35 C40 C39 -176.91(10) . . . . ?
C31 O31 C41 C42 -27.89(10) . . . . ?
C31 O32 C42 C41 -31.74(10) . . . . ?
O31 C41 C42 O32 35.95(10) . . . . ?
C33 C32 C43 O43 -31.99(14) . . . . ?
C31 C32 C43 O43 86.33(12) . . . . ?
C33 C32 C43 N43 148.72(9) . . . . ?
C31 C32 C43 N43 -92.95(11) . . . . ?
O43 C43 N43 C44 176.28(11) . . . . ?
C32 C43 N43 C44 -4.41(17) . . . . ?
O43 C43 N43 C46 -4.65(16) . . . . ?
C32 C43 N43 C46 174.66(10) . . . . ?
C43 N43 C44 O44 3.9(2) . . . . ?
C46 N43 C44 O44 -175.20(14) . . . . ?
C43 N43 C44 O45 -176.69(10) . . . . ?
C46 N43 C44 O45 4.17(13) . . . . ?
O44 C44 O45 C45 -171.88(12) . . . . ?
N43 C44 O45 C45 8.70(13) . . . . ?
C46 C45 O45 C44 -17.60(14) . . . . ?
C43 N43 C46 C45 166.54(10) . . . . ?
C44 N43 C46 C45 -14.23(13) . . . . ?
O45 C45 C46 N43 18.43(13) . . . . ?
C32 C33 C47 O47 -42.27(14) . . . . ?
C34 C33 C47 O47 78.72(13) . . . . ?
C32 C33 C47 O48 140.87(9) . . . . ?
C34 C33 C47 O48 -98.14(10) . . . . ?
O47 C47 O48 C48 -11.07(16) . . . . ?
C33 C47 O48 C48 165.79(9) . . . . ?
C49 C48 O48 C47 -161.02(10) . . . . ?
C35 C34 C50 C55 -45.90(13) . . . . ?
C33 C34 C50 C55 80.16(12) . . . . ?
C35 C34 C50 C51 138.33(10) . . . . ?
C33 C34 C50 C51 -95.61(11) . . . . ?
C55 C50 C51 C52 -1.47(16) . . . . ?
C34 C50 C51 C52 174.40(10) . . . . ?
C50 C51 C52 C53 0.66(17) . . . . ?
C51 C52 C53 C54 0.70(18) . . . . ?
C52 C53 C54 C55 -1.24(18) . . . . ?
C53 C54 C55 C50 0.42(17) . . . . ?
C51 C50 C55 C54 0.93(16) . . . . ?
C34 C50 C55 C54 -174.89(10) . . . . ?
O61 C62 O62 C63 -2.5(4) . . . . ?
C61 C62 O62 C63 178.8(2) . . . . ?
C62 O62 C63 C64 159.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O14 1.00 2.33 2.9721(13) 121.2 . yes
C11 H11A O32 0.99 2.55 3.3876(13) 142.4 . yes
C15 H15B O32 0.99 2.58 3.5456(15) 165.0 2_675 yes
C16 H16A O13 0.99 2.52 3.1041(14) 117.8 2_775 yes
C32 H32 O44 1.00 2.28 2.9582(13) 123.6 . yes
C41 H41A O2 0.99 2.61 3.3991(13) 137.0 1_455 yes
C45 H45A O31 0.99 2.65 3.3334(14) 126.1 2_566 yes
C46 H46A O43 0.99 2.35 3.2956(15) 158.7 2_666 yes
C49 H49A O31 0.98 2.61 3.5122(17) 152.4 1_655 yes
C49 H49B O61 0.98 2.38 3.150(2) 135.4 . yes
C61 H61C O47 0.98 2.55 3.501(3) 162.5 1_655 yes
C64 H64A O44 0.98 2.41 3.351(3) 161.1 2_676 yes

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2975KFMI
_database_code_depnum_ccdc_archive 'CCDC 2087415'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C26 H21 N O2 S2), H2 O'
_chemical_formula_sum            'C104 H86 N4 O9 S8'
_chemical_formula_weight         1792.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6339(2)
_cell_length_b                   15.2440(3)
_cell_length_c                   33.4220(6)
_cell_angle_alpha                83.1131(13)
_cell_angle_beta                 89.8510(13)
_cell_angle_gamma                83.6116(14)
_cell_volume                     4339.73(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      68.63

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    2.424
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_T_max  0.8384
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28242
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         68.681
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             15752
_reflns_number_gt                12023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
JF2975   (MG-4-44-C)   Cu

A colorless plate with approximate orthogonal dimensions 0.016 x 0.083 x 
0.192mm3 was placed and optically centered on the Bruker(1) Venture Dual 
source Kappa Photon100 diffractometer at â\/E?173Â°C(100K).  Indexing of the unit 
cell used a random set of reflections collected from three series of 0.5Â° wide 
omega-scans, 10 seconds per frame, and 30 frames per series that were well 
distributed in reciprocal space. Data were collected [CuKa] with 0.5Â° wide 
scans, variable time per frame dependent upon detector 2theta angle and 
varying Ï? and omega angles such that nearly all unique reflections were 
collected at least once.  The crystal to detector distance was 5.00cm, thus 
providing a complete sphere of data to 2thetamax= 137.26Â°. 

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7 with Intel 
i7-1065G7 at 1.30GHz with four cores, eight logical processors and 16GB of 
extended memory. Data collected were corrected for Lorentz and polarization 
effects with Saint1 and absorption using Blessingâ\/E?s method and merged as 
incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was 
implemented to determine the probable space group and set up the initial 
files. System symmetry, lack of systematic absences and intensity statistics 
indicated the centrosymmetric triclinic space group P-1 (no. 2). The structure 
was determined by direct methods with the location of nearly all of the non-
hydrogen atoms comprising the four unique and nearly identical molecules 
within the asymmetric unit using the program XT(5). An additional water 
molecule was also located and found to be fully occupied over two nearly 
overlapping positions. The structure was refined with XL(6). The 49830 data 
collected were merged for identical indices to 28242 reflections and then for 
least squares refinement to 15752 unique data [R(int)=0.0406]. All non-
hydrogen atoms were refined anisotropically. One of the sulfur containing 
ligands S(13) was optimized for disorder, 0.837:0.13, another similar ligand 
in another molecule had disorder at a carbon atom, C(43) 0.78:0.22, and the 
overlapping water molecule, O(121):O(122), 0.50:0.50  A variety of restraints 
were required for structural refinement and those commands included distance 
restraints (SADI, DFIX), similar thermal motion restraints for atoms that were 
overlapping or nearly so (SIMU).  Hydrogen atoms were idealized throughout the 
final refinement. The final structure was refined to convergence with R
(F)=8.23%, wR(F2)=14.36%, GOF=1.101 for all 15752 unique reflections [R
(F)=6.09, wR(F2)=12.88% for those 12023 data with Fo > 4sigma(Fo)]. The final 
difference-Fourier map was featureless indicating that the structure is both 
correct and complete. 

References:

1.	Bruker (2019) APEX3 (Version 2019.1) and (2016) SAINT (Version 8.37a). 
Bruker AXS Inc., Madison, Wisconsin, USA.
2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. 
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area Detector 
Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., 
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen, 
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen: 
GÃ?ttingen, Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193) 
for the Dual Source X-ray diffractometer.


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+5.6619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ShelXT
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00127(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         15752
_refine_ls_number_parameters     1175
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0839(4) 0.2467(2) 0.54099(9) 0.0328(7) Uani 1 1 d . . . . .
C2 C 0.0832(4) 0.1473(2) 0.55230(9) 0.0350(7) Uani 1 1 d . . . . .
H2 H -0.016275 0.119631 0.551612 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1598(4) 0.1792(2) 0.51385(9) 0.0362(7) Uani 1 1 d . . . . .
H3 H 0.107797 0.174011 0.487664 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3276(4) 0.1483(2) 0.51907(9) 0.0361(7) Uani 1 1 d . . . . .
N4 N 0.3527(3) 0.11075(17) 0.55919(8) 0.0346(6) Uani 1 1 d . . . . .
O4 O 0.4288(3) 0.15173(16) 0.49391(7) 0.0445(6) Uani 1 1 d . . . . .
C5 C 0.2130(4) 0.1053(2) 0.58010(9) 0.0364(7) Uani 1 1 d . . . . .
O5 O 0.2033(3) 0.07201(16) 0.61455(7) 0.0455(6) Uani 1 1 d . . . . .
C6 C 0.1827(4) 0.2960(2) 0.56605(9) 0.0347(7) Uani 1 1 d . . . . .
C7 C 0.1394(4) 0.3103(2) 0.60539(9) 0.0373(7) Uani 1 1 d . . . . .
C8 C 0.2354(5) 0.3551(2) 0.62753(11) 0.0472(9) Uani 1 1 d . . . . .
H8 H 0.207290 0.364890 0.654269 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3693(5) 0.3855(2) 0.61173(12) 0.0501(9) Uani 1 1 d . . . . .
H9 H 0.432214 0.416178 0.627365 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4122(4) 0.3712(2) 0.57281(12) 0.0472(9) Uani 1 1 d . . . . .
H10 H 0.505570 0.391028 0.561814 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3183(4) 0.3278(2) 0.55009(10) 0.0391(7) Uani 1 1 d . . . . .
H11 H 0.346468 0.319576 0.523191 0.047 Uiso 1 1 calc R U . . .
C12 C -0.0113(4) 0.2823(2) 0.62355(10) 0.0416(8) Uani 1 1 d . . . . .
H12 H -0.057965 0.244488 0.605404 0.050 Uiso 0.87 1 calc R U P A 1
H12E H -0.031624 0.233856 0.607242 0.050 Uiso 0.13 1 calc R U P B 2
S12 S 0.01077(12) 0.22185(6) 0.67438(3) 0.0497(2) Uani 1 1 d . . . . .
C13 C -0.2505(15) 0.340(3) 0.6697(3) 0.0601(19) Uani 0.87 1 d D U P C 1
H13A H -0.314152 0.388297 0.681426 0.072 Uiso 0.87 1 calc R U P C 1
H13B H -0.320214 0.297021 0.662045 0.072 Uiso 0.87 1 calc R U P C 1
C13B C -0.244(10) 0.34(2) 0.6673(18) 0.060(2) Uani 0.13 1 d D U P C 2
H13C H -0.284827 0.395813 0.674548 0.072 Uiso 0.13 1 calc R U P C 2
H13D H -0.332687 0.300347 0.668300 0.072 Uiso 0.13 1 calc R U P C 2
S13 S -0.1465(3) 0.38294(13) 0.62718(6) 0.0646(5) Uani 0.87 1 d D . P C 1
S13B S -0.1785(17) 0.3505(10) 0.6167(4) 0.063(3) Uani 0.13 1 d D . P C 2
C14 C -0.1283(5) 0.2941(4) 0.69928(12) 0.0686(13) Uani 1 1 d D . . . .
H14A H -0.178095 0.258863 0.721514 0.082 Uiso 1 1 calc R U . C 1
H14B H -0.073893 0.339140 0.710954 0.082 Uiso 1 1 calc R U . C 1
C15 C -0.0644(4) 0.2984(2) 0.52294(9) 0.0354(7) Uani 1 1 d . . . . .
C16 C -0.0854(4) 0.3910(2) 0.52046(9) 0.0382(7) Uani 1 1 d . . . . .
H16 H -0.010747 0.421373 0.532416 0.046 Uiso 1 1 calc R U . . .
C17 C -0.2150(4) 0.4390(2) 0.50062(10) 0.0427(8) Uani 1 1 d . . . . .
H17 H -0.227226 0.502059 0.498766 0.051 Uiso 1 1 calc R U . . .
C18 C -0.3260(4) 0.3961(2) 0.48359(10) 0.0458(8) Uani 1 1 d . . . . .
H18 H -0.414200 0.429279 0.470054 0.055 Uiso 1 1 calc R U . . .
C19 C -0.3078(4) 0.3045(3) 0.48636(11) 0.0487(9) Uani 1 1 d . . . . .
H19 H -0.384072 0.274615 0.474764 0.058 Uiso 1 1 calc R U . . .
C20 C -0.1787(4) 0.2558(2) 0.50598(11) 0.0444(8) Uani 1 1 d . . . . .
H20 H -0.168024 0.192711 0.507900 0.053 Uiso 1 1 calc R U . . .
C21 C 0.5035(4) 0.0838(2) 0.57680(10) 0.0378(7) Uani 1 1 d . . . . .
C22 C 0.6017(5) 0.0198(3) 0.56070(11) 0.0491(9) Uani 1 1 d . . . . .
H22 H 0.568699 -0.007335 0.538521 0.059 Uiso 1 1 calc R U . . .
C23 C 0.7501(5) -0.0045(3) 0.57742(13) 0.0585(10) Uani 1 1 d . . . . .
H23 H 0.819475 -0.047593 0.566147 0.070 Uiso 1 1 calc R U . . .
C24 C 0.7967(5) 0.0327(3) 0.60974(13) 0.0613(11) Uani 1 1 d . . . . .
H24 H 0.897706 0.015222 0.621118 0.074 Uiso 1 1 calc R U . . .
C25 C 0.6967(5) 0.0961(3) 0.62597(13) 0.0622(11) Uani 1 1 d . . . . .
H25 H 0.729064 0.121513 0.648712 0.075 Uiso 1 1 calc R U . . .
C26 C 0.5493(5) 0.1229(3) 0.60934(11) 0.0509(9) Uani 1 1 d . . . . .
H26 H 0.481245 0.167220 0.620169 0.061 Uiso 1 1 calc R U . . .
C31 C 0.4976(4) 0.7531(2) 0.63219(9) 0.0328(7) Uani 1 1 d . . . . .
C32 C 0.5051(4) 0.8441(2) 0.64652(9) 0.0360(7) Uani 1 1 d . . . . .
H32 H 0.604163 0.872582 0.644257 0.043 Uiso 1 1 calc R U . . .
C33 C 0.4107(4) 0.8377(2) 0.60915(9) 0.0378(7) Uani 1 1 d . . . . .
H33 H 0.448506 0.861352 0.582119 0.045 Uiso 1 1 calc R U . . .
C34 C 0.2460(4) 0.8609(2) 0.62019(9) 0.0375(7) Uani 1 1 d . . . . .
N34 N 0.2416(3) 0.86908(17) 0.66133(7) 0.0328(6) Uani 1 1 d . . . . .
O34 O 0.1315(3) 0.87156(16) 0.59841(7) 0.0463(6) Uani 1 1 d . . . . .
C35 C 0.3912(4) 0.8652(2) 0.67802(9) 0.0351(7) Uani 1 1 d . . . . .
C36 C 0.4106(4) 0.6844(2) 0.65581(9) 0.0333(7) Uani 1 1 d . . . . .
O36 O 0.4175(3) 0.87704(16) 0.71225(7) 0.0433(6) Uani 1 1 d . . . . .
C37 C 0.4677(4) 0.6405(2) 0.69305(9) 0.0362(7) Uani 1 1 d . . . . .
C38 C 0.3870(4) 0.5739(2) 0.71250(11) 0.0477(9) Uani 1 1 d . . . . .
H38 H 0.422865 0.545118 0.738122 0.057 Uiso 1 1 calc R U . . .
C39 C 0.2561(5) 0.5485(3) 0.69544(11) 0.0503(9) Uani 1 1 d . . . . .
H39 H 0.203536 0.502502 0.709221 0.060 Uiso 1 1 calc R U . . .
C40 C 0.2011(4) 0.5902(2) 0.65818(11) 0.0449(8) Uani 1 1 d . . . . .
H40 H 0.111010 0.573066 0.646282 0.054 Uiso 1 1 calc R U . . .
C41 C 0.2789(4) 0.6568(2) 0.63871(10) 0.0383(7) Uani 1 1 d . . . . .
H41 H 0.242425 0.684712 0.613007 0.046 Uiso 1 1 calc R U . . .
C42 C 0.6186(4) 0.6626(2) 0.71013(9) 0.0386(7) Uani 1 1 d . . . . .
H42 H 0.635773 0.723494 0.697405 0.046 Uiso 1 1 calc R U . . .
S42 S 0.78601(12) 0.58690(8) 0.69800(3) 0.0565(3) Uani 1 1 d . . . . .
C43 C 0.8077(7) 0.5240(4) 0.74564(15) 0.0491(12) Uani 0.78 1 d . . P D 1
H43A H 0.732361 0.479252 0.748314 0.059 Uiso 0.78 1 calc R U P D 1
H43B H 0.914162 0.492208 0.748618 0.059 Uiso 0.78 1 calc R U P D 1
C43B C 0.876(2) 0.5673(15) 0.7485(6) 0.055(5) Uani 0.22 1 d . . P D 2
H43C H 0.921104 0.504340 0.753512 0.066 Uiso 0.22 1 calc R U P D 2
H43D H 0.962089 0.604662 0.749050 0.066 Uiso 0.22 1 calc R U P D 2
S43 S 0.61667(11) 0.66502(6) 0.76462(2) 0.0449(2) Uani 1 1 d . . . . .
C44 C 0.7798(6) 0.5841(3) 0.77792(13) 0.0651(12) Uani 1 1 d . . . . .
H44A H 0.873666 0.614391 0.781414 0.078 Uiso 0.78 1 calc R U P D 1
H44B H 0.759717 0.548552 0.803802 0.078 Uiso 0.78 1 calc R U P D 1
H44C H 0.839645 0.604562 0.799578 0.078 Uiso 0.22 1 calc R U P D 2
H44D H 0.740259 0.527868 0.789153 0.078 Uiso 0.22 1 calc R U P D 2
C45 C 0.6388(4) 0.7142(2) 0.61098(9) 0.0355(7) Uani 1 1 d . . . . .
C46 C 0.6319(5) 0.6343(2) 0.59515(10) 0.0484(9) Uani 1 1 d . . . . .
H46 H 0.538981 0.606093 0.597453 0.058 Uiso 1 1 calc R U . . .
C47 C 0.7603(6) 0.5957(3) 0.57601(12) 0.0616(12) Uani 1 1 d . . . . .
H47 H 0.754124 0.541156 0.565312 0.074 Uiso 1 1 calc R U . . .
C48 C 0.8962(5) 0.6350(3) 0.57225(11) 0.0609(12) Uani 1 1 d . . . . .
H48 H 0.983901 0.607848 0.559317 0.073 Uiso 1 1 calc R U . . .
C49 C 0.9028(5) 0.7137(3) 0.58746(11) 0.0552(10) Uani 1 1 d . . . . .
H49 H 0.995974 0.741647 0.584772 0.066 Uiso 1 1 calc R U . . .
C50 C 0.7768(4) 0.7537(3) 0.60668(10) 0.0451(8) Uani 1 1 d . . . . .
H50 H 0.784327 0.808466 0.617032 0.054 Uiso 1 1 calc R U . . .
C51 C 0.1012(4) 0.8830(2) 0.68403(9) 0.0329(7) Uani 1 1 d . . . . .
C52 C 0.0499(4) 0.9673(2) 0.69215(9) 0.0379(7) Uani 1 1 d . . . . .
H52 H 0.105606 1.015891 0.682627 0.046 Uiso 1 1 calc R U . . .
C53 C -0.0845(4) 0.9807(2) 0.71448(11) 0.0460(8) Uani 1 1 d . . . . .
H53 H -0.121946 1.038896 0.720093 0.055 Uiso 1 1 calc R U . . .
C54 C -0.1636(4) 0.9101(3) 0.72849(11) 0.0457(8) Uani 1 1 d . . . . .
H54 H -0.255496 0.919607 0.743796 0.055 Uiso 1 1 calc R U . . .
C55 C -0.1100(5) 0.8254(3) 0.72040(12) 0.0523(9) Uani 1 1 d . . . . .
H55 H -0.164282 0.776523 0.730372 0.063 Uiso 1 1 calc R U . . .
C56 C 0.0235(5) 0.8116(2) 0.69766(11) 0.0482(9) Uani 1 1 d . . . . .
H56 H 0.060450 0.753622 0.691621 0.058 Uiso 1 1 calc R U . . .
C61 C 0.0697(3) 0.7216(2) 0.95991(9) 0.0293(6) Uani 1 1 d . . . . .
C62 C 0.1142(4) 0.6232(2) 0.95780(9) 0.0315(6) Uani 1 1 d . . . . .
H62 H 0.224669 0.596310 0.962508 0.038 Uiso 1 1 calc R U . . .
C63 C 0.0157(4) 0.6511(2) 0.99247(9) 0.0329(7) Uani 1 1 d . . . . .
H63 H 0.062961 0.643957 1.020118 0.040 Uiso 1 1 calc R U . . .
C64 C -0.1388(4) 0.6209(2) 0.98689(9) 0.0345(7) Uani 1 1 d . . . . .
N64 N -0.1388(3) 0.58583(17) 0.94980(7) 0.0318(5) Uani 1 1 d . . . . .
O64 O -0.2484(3) 0.62461(17) 1.00953(7) 0.0442(6) Uani 1 1 d . . . . .
C65 C 0.0082(4) 0.5833(2) 0.93184(9) 0.0334(7) Uani 1 1 d . . . . .
O65 O 0.0397(3) 0.55408(16) 0.90044(7) 0.0445(6) Uani 1 1 d . . . . .
C66 C -0.0449(3) 0.7730(2) 0.92934(9) 0.0307(6) Uani 1 1 d . . . . .
C67 C -0.0106(4) 0.7865(2) 0.88820(9) 0.0328(7) Uani 1 1 d . . . . .
C68 C -0.1238(4) 0.8335(2) 0.86160(10) 0.0414(8) Uani 1 1 d . . . . .
H68 H -0.101419 0.842627 0.833668 0.050 Uiso 1 1 calc R U . . .
C69 C -0.2678(4) 0.8670(3) 0.87497(11) 0.0482(9) Uani 1 1 d . . . . .
H69 H -0.343647 0.898033 0.856348 0.058 Uiso 1 1 calc R U . . .
C70 C -0.3000(4) 0.8551(2) 0.91559(11) 0.0460(8) Uani 1 1 d . . . . .
H70 H -0.398103 0.878288 0.925135 0.055 Uiso 1 1 calc R U . . .
C71 C -0.1889(4) 0.8091(2) 0.94241(10) 0.0373(7) Uani 1 1 d . . . . .
H71 H -0.211390 0.802046 0.970374 0.045 Uiso 1 1 calc R U . . .
C72 C 0.1480(4) 0.7565(2) 0.87211(9) 0.0327(7) Uani 1 1 d . . . . .
H72 H 0.207353 0.715408 0.893760 0.039 Uiso 1 1 calc R U . . .
S72 S 0.14359(11) 0.69952(6) 0.82673(3) 0.0435(2) Uani 1 1 d . . . . .
C73 C 0.3499(5) 0.8193(3) 0.81579(11) 0.0485(9) Uani 1 1 d . . . . .
H73A H 0.388524 0.870623 0.799319 0.058 Uiso 1 1 calc R U . . .
H73B H 0.439480 0.774126 0.823579 0.058 Uiso 1 1 calc R U . . .
S73 S 0.25313(11) 0.85415(6) 0.85987(3) 0.0494(2) Uani 1 1 d . . . . .
C74 C 0.2309(5) 0.7806(3) 0.79247(11) 0.0533(10) Uani 1 1 d . . . . .
H74A H 0.281423 0.751894 0.770009 0.064 Uiso 1 1 calc R U . . .
H74B H 0.150071 0.828135 0.781049 0.064 Uiso 1 1 calc R U . . .
C75 C 0.1906(4) 0.7730(2) 0.97556(9) 0.0319(7) Uani 1 1 d . . . . .
C76 C 0.1411(4) 0.8530(2) 0.99021(10) 0.0408(8) Uani 1 1 d . . . . .
H76 H 0.033977 0.875801 0.988492 0.049 Uiso 1 1 calc R U . . .
C77 C 0.2483(5) 0.8999(3) 1.00741(10) 0.0498(9) Uani 1 1 d . . . . .
H77 H 0.213812 0.954412 1.017422 0.060 Uiso 1 1 calc R U . . .
C78 C 0.4028(5) 0.8678(3) 1.00995(10) 0.0501(10) Uani 1 1 d . . . . .
H78 H 0.475264 0.900171 1.021597 0.060 Uiso 1 1 calc R U . . .
C79 C 0.4528(4) 0.7892(3) 0.99573(11) 0.0500(9) Uani 1 1 d . . . . .
H79 H 0.560154 0.767014 0.997671 0.060 Uiso 1 1 calc R U . . .
C80 C 0.3478(4) 0.7413(2) 0.97842(10) 0.0417(8) Uani 1 1 d . . . . .
H80 H 0.383750 0.686867 0.968549 0.050 Uiso 1 1 calc R U . . .
C81 C -0.2771(4) 0.5662(2) 0.93097(9) 0.0328(7) Uani 1 1 d . . . . .
C82 C -0.3206(4) 0.6084(2) 0.89315(10) 0.0444(8) Uani 1 1 d . . . . .
H82 H -0.257221 0.648968 0.879257 0.053 Uiso 1 1 calc R U . . .
C83 C -0.4576(4) 0.5912(3) 0.87564(11) 0.0490(9) Uani 1 1 d . . . . .
H83 H -0.486625 0.619062 0.849360 0.059 Uiso 1 1 calc R U . . .
C84 C -0.5521(4) 0.5341(2) 0.89589(10) 0.0420(8) Uani 1 1 d . . . . .
H84 H -0.646927 0.523661 0.883913 0.050 Uiso 1 1 calc R U . . .
C85 C -0.5080(4) 0.4920(2) 0.93385(10) 0.0391(7) Uani 1 1 d . . . . .
H85 H -0.572543 0.452328 0.947940 0.047 Uiso 1 1 calc R U . . .
C86 C -0.3696(4) 0.5077(2) 0.95129(10) 0.0355(7) Uani 1 1 d . . . . .
H86 H -0.338519 0.478226 0.977158 0.043 Uiso 1 1 calc R U . . .
C91 C 0.5581(4) 0.2182(2) 0.87615(8) 0.0307(6) Uani 1 1 d . . . . .
C92 C 0.5208(4) 0.3155(2) 0.85875(9) 0.0337(7) Uani 1 1 d . . . . .
H92 H 0.411321 0.345056 0.857946 0.040 Uiso 1 1 calc R U . . .
C93 C 0.6106(4) 0.2936(2) 0.89815(9) 0.0336(7) Uani 1 1 d . . . . .
H93 H 0.557488 0.307278 0.923660 0.040 Uiso 1 1 calc R U . . .
C94 C 0.7682(4) 0.3202(2) 0.89025(9) 0.0338(7) Uani 1 1 d . . . . .
N94 N 0.7794(3) 0.34443(17) 0.84838(8) 0.0349(6) Uani 1 1 d . . . . .
O94 O 0.8713(3) 0.32283(15) 0.91414(7) 0.0430(6) Uani 1 1 d . . . . .
C95 C 0.6372(4) 0.3458(2) 0.82846(9) 0.0341(7) Uani 1 1 d . . . . .
O95 O 0.6141(3) 0.36803(16) 0.79269(7) 0.0439(6) Uani 1 1 d . . . . .
C96 C 0.6761(4) 0.1600(2) 0.85486(9) 0.0313(6) Uani 1 1 d . . . . .
C97 C 0.6429(4) 0.1353(2) 0.81692(9) 0.0314(6) Uani 1 1 d . . . . .
C98 C 0.7564(4) 0.0821(2) 0.79843(10) 0.0364(7) Uani 1 1 d . . . . .
H98 H 0.734715 0.065525 0.772688 0.044 Uiso 1 1 calc R U . . .
C99 C 0.8995(4) 0.0528(2) 0.81650(10) 0.0405(8) Uani 1 1 d . . . . .
H99 H 0.975800 0.017376 0.803117 0.049 Uiso 1 1 calc R U . . .
C100 C 0.9306(4) 0.0755(2) 0.85428(10) 0.0401(8) Uani 1 1 d . . . . .
H100 H 1.028044 0.054908 0.867149 0.048 Uiso 1 1 calc R U . . .
C101 C 0.8199(4) 0.1280(2) 0.87332(10) 0.0373(7) Uani 1 1 d . . . . .
H101 H 0.841787 0.142692 0.899402 0.045 Uiso 1 1 calc R U . . .
C102 C 0.4855(4) 0.1622(2) 0.79626(9) 0.0348(7) Uani 1 1 d . . . . .
H102 H 0.429989 0.211362 0.809904 0.042 Uiso 1 1 calc R U . . .
S102 S 0.36977(12) 0.06786(7) 0.80282(3) 0.0530(3) Uani 1 1 d . . . . .
C103 C 0.2974(5) 0.0749(3) 0.75213(11) 0.0527(10) Uani 1 1 d . . . . .
H10A H 0.271514 0.015910 0.746424 0.063 Uiso 1 1 calc R U . . .
H10B H 0.201596 0.117343 0.748496 0.063 Uiso 1 1 calc R U . . .
S103 S 0.49279(11) 0.20074(7) 0.74245(2) 0.0471(2) Uani 1 1 d . . . . .
C104 C 0.4203(5) 0.1056(3) 0.72400(11) 0.0568(10) Uani 1 1 d . . . . .
H10C H 0.376041 0.122500 0.696505 0.068 Uiso 1 1 calc R U . . .
H10D H 0.506268 0.057219 0.722928 0.068 Uiso 1 1 calc R U . . .
C105 C 0.4261(4) 0.1742(2) 0.89609(9) 0.0328(7) Uani 1 1 d . . . . .
C106 C 0.2985(4) 0.2223(2) 0.91183(10) 0.0406(8) Uani 1 1 d . . . . .
H106 H 0.291550 0.285376 0.908804 0.049 Uiso 1 1 calc R U . . .
C107 C 0.1818(4) 0.1803(2) 0.93175(10) 0.0437(8) Uani 1 1 d . . . . .
H107 H 0.096120 0.214463 0.942415 0.052 Uiso 1 1 calc R U . . .
C108 C 0.1896(4) 0.0884(2) 0.93617(10) 0.0436(8) Uani 1 1 d . . . . .
H108 H 0.109268 0.059384 0.949811 0.052 Uiso 1 1 calc R U . . .
C109 C 0.3149(4) 0.0389(2) 0.92066(9) 0.0386(7) Uani 1 1 d . . . . .
H109 H 0.320381 -0.024152 0.923602 0.046 Uiso 1 1 calc R U . . .
C110 C 0.4326(4) 0.0812(2) 0.90081(9) 0.0356(7) Uani 1 1 d . . . . .
H110 H 0.518381 0.046766 0.890324 0.043 Uiso 1 1 calc R U . . .
C111 C 0.9241(4) 0.3574(2) 0.82836(9) 0.0336(7) Uani 1 1 d . . . . .
C112 C 0.9792(4) 0.2993(2) 0.80119(10) 0.0384(7) Uani 1 1 d . . . . .
H112 H 0.922718 0.251768 0.796036 0.046 Uiso 1 1 calc R U . . .
C113 C 1.1181(4) 0.3123(2) 0.78181(11) 0.0434(8) Uani 1 1 d . . . . .
H113 H 1.156805 0.273378 0.763000 0.052 Uiso 1 1 calc R U . . .
C114 C 1.2013(4) 0.3811(2) 0.78946(11) 0.0450(8) Uani 1 1 d . . . . .
H114 H 1.296236 0.389605 0.775888 0.054 Uiso 1 1 calc R U . . .
C115 C 1.1454(4) 0.4372(2) 0.81689(11) 0.0462(9) Uani 1 1 d . . . . .
H115 H 1.202501 0.484380 0.822282 0.055 Uiso 1 1 calc R U . . .
C116 C 1.0066(4) 0.4255(2) 0.83669(10) 0.0390(8) Uani 1 1 d . . . . .
H116 H 0.968865 0.463938 0.855773 0.047 Uiso 1 1 calc R U . . .
O121 O 0.2059(14) 0.9525(7) 0.5178(3) 0.081(3) Uani 0.5 1 d D . P E 1
H12A H 0.217(14) 0.916(5) 0.5390(17) 0.122 Uiso 0.5 1 d D U P F 1
H12B H 0.265(11) 0.931(7) 0.501(2) 0.122 Uiso 0.5 1 d D U P G 1
O122 O 0.1059(16) 0.9654(8) 0.5185(4) 0.099(4) Uani 0.5 1 d D . P H 2
H12C H 0.083(18) 0.958(7) 0.5430(12) 0.149 Uiso 0.5 1 d D U P I 2
H12D H 0.10(2) 0.916(4) 0.510(3) 0.149 Uiso 0.5 1 d D U P J 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.513(4) . ?
C1 C6 1.513(4) . ?
C1 C2 1.518(4) . ?
C1 C3 1.544(4) . ?
C2 C5 1.494(5) . ?
C2 C3 1.497(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.477(5) . ?
C3 H3 1.0000 . ?
C4 O4 1.212(4) . ?
C4 N4 1.401(4) . ?
N4 C5 1.398(4) . ?
N4 C21 1.427(4) . ?
C5 O5 1.208(4) . ?
C6 C11 1.397(5) . ?
C6 C7 1.401(4) . ?
C7 C8 1.397(5) . ?
C7 C12 1.517(5) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 S13B 1.681(15) . ?
C12 S12 1.833(3) . ?
C12 S13 1.837(4) . ?
C12 H12 1.0000 . ?
C12 H12E 1.0000 . ?
S12 C14 1.808(4) . ?
C13 C14 1.500(6) . ?
C13 S13 1.779(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13B C14 1.500(11) . ?
C13B S13B 1.779(18) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.394(5) . ?
C15 C20 1.398(5) . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 C26 1.379(5) . ?
C22 C23 1.392(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.361(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.503(4) . ?
C31 C45 1.509(4) . ?
C31 C32 1.529(4) . ?
C31 C33 1.539(4) . ?
C32 C35 1.478(4) . ?
C32 C33 1.512(5) . ?
C32 H32 1.0000 . ?
C33 C34 1.483(5) . ?
C33 H33 1.0000 . ?
C34 O34 1.214(4) . ?
C34 N34 1.395(4) . ?
N34 C35 1.401(4) . ?
N34 C51 1.437(4) . ?
C35 O36 1.205(4) . ?
C36 C41 1.401(5) . ?
C36 C37 1.403(4) . ?
C37 C38 1.392(5) . ?
C37 C42 1.512(5) . ?
C38 C39 1.380(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.388(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.377(5) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 S42 1.823(3) . ?
C42 S43 1.826(3) . ?
C42 H42 1.0000 . ?
S42 C43 1.756(5) . ?
S42 C43B 1.836(19) . ?
C43 C44 1.499(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43B C44 1.31(2) . ?
C43B H43C 0.9900 . ?
C43B H43D 0.9900 . ?
S43 C44 1.785(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 H44C 0.9900 . ?
C44 H44D 0.9900 . ?
C45 C46 1.392(5) . ?
C45 C50 1.393(5) . ?
C46 C47 1.388(5) . ?
C46 H46 0.9500 . ?
C47 C48 1.375(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.366(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.382(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.370(4) . ?
C51 C56 1.374(5) . ?
C52 C53 1.388(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.373(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.381(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.389(5) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C75 1.504(4) . ?
C61 C66 1.509(4) . ?
C61 C62 1.516(4) . ?
C61 C63 1.544(4) . ?
C62 C65 1.489(4) . ?
C62 C63 1.510(4) . ?
C62 H62 1.0000 . ?
C63 C64 1.478(5) . ?
C63 H63 1.0000 . ?
C64 O64 1.211(4) . ?
C64 N64 1.408(4) . ?
N64 C65 1.401(4) . ?
N64 C81 1.428(4) . ?
C65 O65 1.207(4) . ?
C66 C71 1.394(4) . ?
C66 C67 1.401(4) . ?
C67 C68 1.398(4) . ?
C67 C72 1.513(4) . ?
C68 C69 1.384(5) . ?
C68 H68 0.9500 . ?
C69 C70 1.380(5) . ?
C69 H69 0.9500 . ?
C70 C71 1.385(5) . ?
C70 H70 0.9500 . ?
C71 H71 0.9500 . ?
C72 S73 1.833(3) . ?
C72 S72 1.839(3) . ?
C72 H72 1.0000 . ?
S72 C74 1.809(4) . ?
C73 C74 1.503(5) . ?
C73 S73 1.798(4) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 C80 1.388(5) . ?
C75 C76 1.392(5) . ?
C76 C77 1.395(5) . ?
C76 H76 0.9500 . ?
C77 C78 1.368(6) . ?
C77 H77 0.9500 . ?
C78 C79 1.367(6) . ?
C78 H78 0.9500 . ?
C79 C80 1.393(5) . ?
C79 H79 0.9500 . ?
C80 H80 0.9500 . ?
C81 C86 1.380(4) . ?
C81 C82 1.381(4) . ?
C82 C83 1.386(5) . ?
C82 H82 0.9500 . ?
C83 C84 1.376(5) . ?
C83 H83 0.9500 . ?
C84 C85 1.385(5) . ?
C84 H84 0.9500 . ?
C85 C86 1.388(5) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C91 C105 1.501(4) . ?
C91 C96 1.509(4) . ?
C91 C92 1.527(4) . ?
C91 C93 1.545(4) . ?
C92 C95 1.495(4) . ?
C92 C93 1.513(4) . ?
C92 H92 1.0000 . ?
C93 C94 1.477(5) . ?
C93 H93 1.0000 . ?
C94 O94 1.205(4) . ?
C94 N94 1.410(4) . ?
N94 C95 1.395(4) . ?
N94 C111 1.437(4) . ?
C95 O95 1.214(4) . ?
C96 C101 1.398(4) . ?
C96 C97 1.404(4) . ?
C97 C98 1.393(4) . ?
C97 C102 1.518(4) . ?
C98 C99 1.381(5) . ?
C98 H98 0.9500 . ?
C99 C100 1.383(5) . ?
C99 H99 0.9500 . ?
C100 C101 1.382(5) . ?
C100 H100 0.9500 . ?
C101 H101 0.9500 . ?
C102 S103 1.827(3) . ?
C102 S102 1.833(3) . ?
C102 H102 1.0000 . ?
S102 C103 1.794(4) . ?
C103 C104 1.493(6) . ?
C103 H10A 0.9900 . ?
C103 H10B 0.9900 . ?
S103 C104 1.816(4) . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C105 C106 1.392(4) . ?
C105 C110 1.402(4) . ?
C106 C107 1.380(5) . ?
C106 H106 0.9500 . ?
C107 C108 1.386(5) . ?
C107 H107 0.9500 . ?
C108 C109 1.385(5) . ?
C108 H108 0.9500 . ?
C109 C110 1.388(5) . ?
C109 H109 0.9500 . ?
C110 H110 0.9500 . ?
C111 C116 1.378(4) . ?
C111 C112 1.390(4) . ?
C112 C113 1.383(5) . ?
C112 H112 0.9500 . ?
C113 C114 1.384(5) . ?
C113 H113 0.9500 . ?
C114 C115 1.378(5) . ?
C114 H114 0.9500 . ?
C115 C116 1.386(5) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
O121 H12A 0.842(5) . ?
O121 H12B 0.842(5) . ?
O122 H12C 0.842(5) . ?
O122 H12D 0.842(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C1 C6 116.4(3) . . ?
C15 C1 C2 117.4(3) . . ?
C6 C1 C2 118.3(3) . . ?
C15 C1 C3 112.9(3) . . ?
C6 C1 C3 121.0(3) . . ?
C2 C1 C3 58.5(2) . . ?
C5 C2 C3 105.6(3) . . ?
C5 C2 C1 114.2(3) . . ?
C3 C2 C1 61.6(2) . . ?
C5 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 106.4(3) . . ?
C4 C3 C1 118.9(3) . . ?
C2 C3 C1 59.9(2) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C1 C3 H3 118.8 . . ?
O4 C4 N4 124.2(3) . . ?
O4 C4 C3 128.0(3) . . ?
N4 C4 C3 107.8(3) . . ?
C5 N4 C4 112.0(3) . . ?
C5 N4 C21 124.2(3) . . ?
C4 N4 C21 123.8(3) . . ?
O5 C5 N4 124.6(3) . . ?
O5 C5 C2 127.7(3) . . ?
N4 C5 C2 107.8(3) . . ?
C11 C6 C7 119.3(3) . . ?
C11 C6 C1 120.2(3) . . ?
C7 C6 C1 120.6(3) . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 C12 119.7(3) . . ?
C6 C7 C12 121.8(3) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C6 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C7 C12 S13B 120.7(6) . . ?
C7 C12 S12 114.2(2) . . ?
S13B C12 S12 113.3(5) . . ?
C7 C12 S13 108.3(2) . . ?
S12 C12 S13 107.00(18) . . ?
C7 C12 H12 109.1 . . ?
S12 C12 H12 109.1 . . ?
S13 C12 H12 109.1 . . ?
C7 C12 H12E 101.5 . . ?
S13B C12 H12E 101.5 . . ?
S12 C12 H12E 101.5 . . ?
C14 S12 C12 97.69(19) . . ?
C14 C13 S13 105.5(8) . . ?
C14 C13 H13A 110.6 . . ?
S13 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
S13 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C14 C13B S13B 117.7(15) . . ?
C14 C13B H13C 107.9 . . ?
S13B C13B H13C 107.9 . . ?
C14 C13B H13D 107.9 . . ?
S13B C13B H13D 107.9 . . ?
H13C C13B H13D 107.2 . . ?
C13 S13 C12 96.9(11) . . ?
C12 S13B C13B 97(3) . . ?
C13 C14 S12 110.0(10) . . ?
C13B C14 S12 106(7) . . ?
C13 C14 H14A 109.7 . . ?
S12 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
S12 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C20 118.2(3) . . ?
C16 C15 C1 120.4(3) . . ?
C20 C15 C1 121.2(3) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C26 121.1(3) . . ?
C22 C21 N4 119.4(3) . . ?
C26 C21 N4 119.6(3) . . ?
C21 C22 C23 119.0(4) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.9(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.7(4) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C36 C31 C45 113.6(3) . . ?
C36 C31 C32 120.8(3) . . ?
C45 C31 C32 117.1(3) . . ?
C36 C31 C33 121.1(3) . . ?
C45 C31 C33 114.6(3) . . ?
C32 C31 C33 59.1(2) . . ?
C35 C32 C33 106.2(3) . . ?
C35 C32 C31 114.3(3) . . ?
C33 C32 C31 60.8(2) . . ?
C35 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 105.3(3) . . ?
C34 C33 C31 116.9(3) . . ?
C32 C33 C31 60.1(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C31 C33 H33 119.6 . . ?
O34 C34 N34 123.9(3) . . ?
O34 C34 C33 128.0(3) . . ?
N34 C34 C33 108.1(3) . . ?
C34 N34 C35 112.0(3) . . ?
C34 N34 C51 124.7(3) . . ?
C35 N34 C51 123.3(2) . . ?
O36 C35 N34 124.4(3) . . ?
O36 C35 C32 127.8(3) . . ?
N34 C35 C32 107.8(3) . . ?
C41 C36 C37 118.9(3) . . ?
C41 C36 C31 119.7(3) . . ?
C37 C36 C31 121.1(3) . . ?
C38 C37 C36 118.6(3) . . ?
C38 C37 C42 121.4(3) . . ?
C36 C37 C42 119.9(3) . . ?
C39 C38 C37 121.6(3) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C40 120.1(3) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C41 C40 C39 119.0(3) . . ?
C41 C40 H40 120.5 . . ?
C39 C40 H40 120.5 . . ?
C40 C41 C36 121.7(3) . . ?
C40 C41 H41 119.1 . . ?
C36 C41 H41 119.1 . . ?
C37 C42 S42 112.5(2) . . ?
C37 C42 S43 113.9(2) . . ?
S42 C42 S43 108.26(17) . . ?
C37 C42 H42 107.3 . . ?
S42 C42 H42 107.3 . . ?
S43 C42 H42 107.3 . . ?
C43 S42 C42 96.9(2) . . ?
C42 S42 C43B 97.2(6) . . ?
C44 C43 S42 109.7(3) . . ?
C44 C43 H43A 109.7 . . ?
S42 C43 H43A 109.7 . . ?
C44 C43 H43B 109.7 . . ?
S42 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
C44 C43B S42 114.7(13) . . ?
C44 C43B H43C 108.6 . . ?
S42 C43B H43C 108.6 . . ?
C44 C43B H43D 108.6 . . ?
S42 C43B H43D 108.6 . . ?
H43C C43B H43D 107.6 . . ?
C44 S43 C42 98.62(18) . . ?
C43B C44 S43 115.8(9) . . ?
C43 C44 S43 110.1(3) . . ?
C43 C44 H44A 109.6 . . ?
S43 C44 H44A 109.6 . . ?
C43 C44 H44B 109.6 . . ?
S43 C44 H44B 109.6 . . ?
H44A C44 H44B 108.2 . . ?
C43B C44 H44C 108.3 . . ?
S43 C44 H44C 108.3 . . ?
C43B C44 H44D 108.3 . . ?
S43 C44 H44D 108.3 . . ?
H44C C44 H44D 107.4 . . ?
C46 C45 C50 118.1(3) . . ?
C46 C45 C31 118.6(3) . . ?
C50 C45 C31 123.4(3) . . ?
C47 C46 C45 120.2(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C48 C47 C46 121.1(4) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C49 C48 C47 118.8(4) . . ?
C49 C48 H48 120.6 . . ?
C47 C48 H48 120.6 . . ?
C48 C49 C50 121.4(4) . . ?
C48 C49 H49 119.3 . . ?
C50 C49 H49 119.3 . . ?
C49 C50 C45 120.4(4) . . ?
C49 C50 H50 119.8 . . ?
C45 C50 H50 119.8 . . ?
C52 C51 C56 121.7(3) . . ?
C52 C51 N34 119.0(3) . . ?
C56 C51 N34 119.3(3) . . ?
C51 C52 C53 119.0(3) . . ?
C51 C52 H52 120.5 . . ?
C53 C52 H52 120.5 . . ?
C54 C53 C52 120.2(3) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 120.2(3) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C54 C55 C56 119.9(3) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C51 C56 C55 119.0(3) . . ?
C51 C56 H56 120.5 . . ?
C55 C56 H56 120.5 . . ?
C75 C61 C66 116.1(3) . . ?
C75 C61 C62 117.5(3) . . ?
C66 C61 C62 119.0(2) . . ?
C75 C61 C63 112.5(2) . . ?
C66 C61 C63 120.5(3) . . ?
C62 C61 C63 59.1(2) . . ?
C65 C62 C63 105.5(3) . . ?
C65 C62 C61 113.8(3) . . ?
C63 C62 C61 61.4(2) . . ?
C65 C62 H62 120.4 . . ?
C63 C62 H62 120.4 . . ?
C61 C62 H62 120.4 . . ?
C64 C63 C62 106.3(2) . . ?
C64 C63 C61 117.6(3) . . ?
C62 C63 C61 59.52(19) . . ?
C64 C63 H63 119.3 . . ?
C62 C63 H63 119.3 . . ?
C61 C63 H63 119.3 . . ?
O64 C64 N64 124.5(3) . . ?
O64 C64 C63 127.5(3) . . ?
N64 C64 C63 108.0(3) . . ?
C65 N64 C64 111.7(3) . . ?
C65 N64 C81 124.7(3) . . ?
C64 N64 C81 123.2(3) . . ?
O65 C65 N64 124.7(3) . . ?
O65 C65 C62 127.1(3) . . ?
N64 C65 C62 108.2(3) . . ?
C71 C66 C67 118.8(3) . . ?
C71 C66 C61 119.1(3) . . ?
C67 C66 C61 122.1(3) . . ?
C68 C67 C66 118.8(3) . . ?
C68 C67 C72 119.1(3) . . ?
C66 C67 C72 122.0(3) . . ?
C69 C68 C67 121.6(3) . . ?
C69 C68 H68 119.2 . . ?
C67 C68 H68 119.2 . . ?
C70 C69 C68 119.4(3) . . ?
C70 C69 H69 120.3 . . ?
C68 C69 H69 120.3 . . ?
C69 C70 C71 119.7(3) . . ?
C69 C70 H70 120.1 . . ?
C71 C70 H70 120.1 . . ?
C70 C71 C66 121.6(3) . . ?
C70 C71 H71 119.2 . . ?
C66 C71 H71 119.2 . . ?
C67 C72 S73 108.7(2) . . ?
C67 C72 S72 114.7(2) . . ?
S73 C72 S72 107.84(16) . . ?
C67 C72 H72 108.5 . . ?
S73 C72 H72 108.5 . . ?
S72 C72 H72 108.5 . . ?
C74 S72 C72 97.73(16) . . ?
C74 C73 S73 106.5(3) . . ?
C74 C73 H73A 110.4 . . ?
S73 C73 H73A 110.4 . . ?
C74 C73 H73B 110.4 . . ?
S73 C73 H73B 110.4 . . ?
H73A C73 H73B 108.6 . . ?
C73 S73 C72 97.21(16) . . ?
C73 C74 S72 107.9(2) . . ?
C73 C74 H74A 110.1 . . ?
S72 C74 H74A 110.1 . . ?
C73 C74 H74B 110.1 . . ?
S72 C74 H74B 110.1 . . ?
H74A C74 H74B 108.4 . . ?
C80 C75 C76 118.7(3) . . ?
C80 C75 C61 122.8(3) . . ?
C76 C75 C61 118.4(3) . . ?
C75 C76 C77 120.1(3) . . ?
C75 C76 H76 119.9 . . ?
C77 C76 H76 119.9 . . ?
C78 C77 C76 120.4(4) . . ?
C78 C77 H77 119.8 . . ?
C76 C77 H77 119.8 . . ?
C79 C78 C77 120.0(3) . . ?
C79 C78 H78 120.0 . . ?
C77 C78 H78 120.0 . . ?
C78 C79 C80 120.6(4) . . ?
C78 C79 H79 119.7 . . ?
C80 C79 H79 119.7 . . ?
C75 C80 C79 120.2(3) . . ?
C75 C80 H80 119.9 . . ?
C79 C80 H80 119.9 . . ?
C86 C81 C82 120.3(3) . . ?
C86 C81 N64 119.8(3) . . ?
C82 C81 N64 119.8(3) . . ?
C81 C82 C83 119.5(3) . . ?
C81 C82 H82 120.3 . . ?
C83 C82 H82 120.3 . . ?
C84 C83 C82 120.7(3) . . ?
C84 C83 H83 119.6 . . ?
C82 C83 H83 119.6 . . ?
C83 C84 C85 119.6(3) . . ?
C83 C84 H84 120.2 . . ?
C85 C84 H84 120.2 . . ?
C84 C85 C86 120.0(3) . . ?
C84 C85 H85 120.0 . . ?
C86 C85 H85 120.0 . . ?
C81 C86 C85 119.9(3) . . ?
C81 C86 H86 120.1 . . ?
C85 C86 H86 120.1 . . ?
C105 C91 C96 116.6(3) . . ?
C105 C91 C92 116.2(3) . . ?
C96 C91 C92 118.4(3) . . ?
C105 C91 C93 114.1(2) . . ?
C96 C91 C93 120.1(3) . . ?
C92 C91 C93 59.01(19) . . ?
C95 C92 C93 105.1(3) . . ?
C95 C92 C91 112.9(3) . . ?
C93 C92 C91 61.11(19) . . ?
C95 C92 H92 120.8 . . ?
C93 C92 H92 120.8 . . ?
C91 C92 H92 120.8 . . ?
C94 C93 C92 106.5(3) . . ?
C94 C93 C91 118.4(3) . . ?
C92 C93 C91 59.89(19) . . ?
C94 C93 H93 118.9 . . ?
C92 C93 H93 118.9 . . ?
C91 C93 H93 118.9 . . ?
O94 C94 N94 124.1(3) . . ?
O94 C94 C93 128.3(3) . . ?
N94 C94 C93 107.5(3) . . ?
C95 N94 C94 112.1(3) . . ?
C95 N94 C111 124.1(3) . . ?
C94 N94 C111 123.5(3) . . ?
O95 C95 N94 125.2(3) . . ?
O95 C95 C92 126.7(3) . . ?
N94 C95 C92 108.1(3) . . ?
C101 C96 C97 118.9(3) . . ?
C101 C96 C91 120.0(3) . . ?
C97 C96 C91 121.1(3) . . ?
C98 C97 C96 118.8(3) . . ?
C98 C97 C102 119.2(3) . . ?
C96 C97 C102 122.0(3) . . ?
C99 C98 C97 121.8(3) . . ?
C99 C98 H98 119.1 . . ?
C97 C98 H98 119.1 . . ?
C98 C99 C100 119.3(3) . . ?
C98 C99 H99 120.3 . . ?
C100 C99 H99 120.3 . . ?
C101 C100 C99 120.0(3) . . ?
C101 C100 H100 120.0 . . ?
C99 C100 H100 120.0 . . ?
C100 C101 C96 121.1(3) . . ?
C100 C101 H101 119.4 . . ?
C96 C101 H101 119.4 . . ?
C97 C102 S103 115.2(2) . . ?
C97 C102 S102 109.3(2) . . ?
S103 C102 S102 108.22(16) . . ?
C97 C102 H102 108.0 . . ?
S103 C102 H102 108.0 . . ?
S102 C102 H102 108.0 . . ?
C103 S102 C102 98.51(17) . . ?
C104 C103 S102 108.5(3) . . ?
C104 C103 H10A 110.0 . . ?
S102 C103 H10A 110.0 . . ?
C104 C103 H10B 110.0 . . ?
S102 C103 H10B 110.0 . . ?
H10A C103 H10B 108.4 . . ?
C104 S103 C102 97.60(17) . . ?
C103 C104 S103 108.0(3) . . ?
C103 C104 H10C 110.1 . . ?
S103 C104 H10C 110.1 . . ?
C103 C104 H10D 110.1 . . ?
S103 C104 H10D 110.1 . . ?
H10C C104 H10D 108.4 . . ?
C106 C105 C110 118.0(3) . . ?
C106 C105 C91 122.3(3) . . ?
C110 C105 C91 119.6(3) . . ?
C107 C106 C105 121.4(3) . . ?
C107 C106 H106 119.3 . . ?
C105 C106 H106 119.3 . . ?
C106 C107 C108 120.0(3) . . ?
C106 C107 H107 120.0 . . ?
C108 C107 H107 120.0 . . ?
C109 C108 C107 119.8(3) . . ?
C109 C108 H108 120.1 . . ?
C107 C108 H108 120.1 . . ?
C108 C109 C110 120.2(3) . . ?
C108 C109 H109 119.9 . . ?
C110 C109 H109 119.9 . . ?
C109 C110 C105 120.6(3) . . ?
C109 C110 H110 119.7 . . ?
C105 C110 H110 119.7 . . ?
C116 C111 C112 121.2(3) . . ?
C116 C111 N94 120.1(3) . . ?
C112 C111 N94 118.7(3) . . ?
C113 C112 C111 118.6(3) . . ?
C113 C112 H112 120.7 . . ?
C111 C112 H112 120.7 . . ?
C112 C113 C114 120.9(3) . . ?
C112 C113 H113 119.6 . . ?
C114 C113 H113 119.6 . . ?
C115 C114 C113 119.6(3) . . ?
C115 C114 H114 120.2 . . ?
C113 C114 H114 120.2 . . ?
C114 C115 C116 120.6(3) . . ?
C114 C115 H115 119.7 . . ?
C116 C115 H115 119.7 . . ?
C111 C116 C115 119.2(3) . . ?
C111 C116 H116 120.4 . . ?
C115 C116 H116 120.4 . . ?
H12A O121 H12B 106.5(9) . . ?
H12C O122 H12D 106.6(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C1 C2 C5 -163.4(3) . . . . ?
C6 C1 C2 C5 -15.6(4) . . . . ?
C3 C1 C2 C5 95.3(3) . . . . ?
C15 C1 C2 C3 101.3(3) . . . . ?
C6 C1 C2 C3 -110.9(3) . . . . ?
C5 C2 C3 C4 4.8(3) . . . . ?
C1 C2 C3 C4 114.3(3) . . . . ?
C5 C2 C3 C1 -109.5(3) . . . . ?
C15 C1 C3 C4 157.8(3) . . . . ?
C6 C1 C3 C4 13.2(4) . . . . ?
C2 C1 C3 C4 -93.1(3) . . . . ?
C15 C1 C3 C2 -109.1(3) . . . . ?
C6 C1 C3 C2 106.3(3) . . . . ?
C2 C3 C4 O4 171.7(3) . . . . ?
C1 C3 C4 O4 -124.1(3) . . . . ?
C2 C3 C4 N4 -6.8(3) . . . . ?
C1 C3 C4 N4 57.4(4) . . . . ?
O4 C4 N4 C5 -172.1(3) . . . . ?
C3 C4 N4 C5 6.4(3) . . . . ?
O4 C4 N4 C21 9.6(5) . . . . ?
C3 C4 N4 C21 -171.8(3) . . . . ?
C4 N4 C5 O5 176.7(3) . . . . ?
C21 N4 C5 O5 -5.1(5) . . . . ?
C4 N4 C5 C2 -3.3(3) . . . . ?
C21 N4 C5 C2 174.9(3) . . . . ?
C3 C2 C5 O5 178.9(3) . . . . ?
C1 C2 C5 O5 113.5(4) . . . . ?
C3 C2 C5 N4 -1.2(3) . . . . ?
C1 C2 C5 N4 -66.6(3) . . . . ?
C15 C1 C6 C11 -103.2(3) . . . . ?
C2 C1 C6 C11 108.7(3) . . . . ?
C3 C1 C6 C11 40.3(4) . . . . ?
C15 C1 C6 C7 76.7(4) . . . . ?
C2 C1 C6 C7 -71.4(4) . . . . ?
C3 C1 C6 C7 -139.8(3) . . . . ?
C11 C6 C7 C8 -0.9(5) . . . . ?
C1 C6 C7 C8 179.2(3) . . . . ?
C11 C6 C7 C12 176.3(3) . . . . ?
C1 C6 C7 C12 -3.7(5) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
C12 C7 C8 C9 -176.9(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C6 -1.7(5) . . . . ?
C7 C6 C11 C10 1.6(5) . . . . ?
C1 C6 C11 C10 -178.5(3) . . . . ?
C8 C7 C12 S13B 90.2(6) . . . . ?
C6 C7 C12 S13B -86.9(6) . . . . ?
C8 C7 C12 S12 -50.3(4) . . . . ?
C6 C7 C12 S12 132.6(3) . . . . ?
C8 C7 C12 S13 68.8(4) . . . . ?
C6 C7 C12 S13 -108.3(3) . . . . ?
C7 C12 S12 C14 123.8(3) . . . . ?
S13B C12 S12 C14 -19.7(6) . . . . ?
S13 C12 S12 C14 3.9(3) . . . . ?
C14 C13 S13 C12 46(3) . . . . ?
C7 C12 S13 C13 -150.9(12) . . . . ?
S12 C12 S13 C13 -27.3(12) . . . . ?
C7 C12 S13B C13B -135(11) . . . . ?
S12 C12 S13B C13B 6(11) . . . . ?
C14 C13B S13B C12 15(23) . . . . ?
S13 C13 C14 S12 -49(3) . . . . ?
S13B C13B C14 S12 -28(24) . . . . ?
C12 S12 C14 C13 27.2(18) . . . . ?
C12 S12 C14 C13B 27(12) . . . . ?
C6 C1 C15 C16 16.7(4) . . . . ?
C2 C1 C15 C16 165.1(3) . . . . ?
C3 C1 C15 C16 -129.7(3) . . . . ?
C6 C1 C15 C20 -167.6(3) . . . . ?
C2 C1 C15 C20 -19.1(4) . . . . ?
C3 C1 C15 C20 46.1(4) . . . . ?
C20 C15 C16 C17 -1.7(5) . . . . ?
C1 C15 C16 C17 174.1(3) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C16 C15 C20 C19 1.5(5) . . . . ?
C1 C15 C20 C19 -174.3(3) . . . . ?
C5 N4 C21 C22 122.0(4) . . . . ?
C4 N4 C21 C22 -60.0(4) . . . . ?
C5 N4 C21 C26 -58.7(5) . . . . ?
C4 N4 C21 C26 119.3(4) . . . . ?
C26 C21 C22 C23 -0.9(6) . . . . ?
N4 C21 C22 C23 178.4(3) . . . . ?
C21 C22 C23 C24 1.4(6) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 -0.7(7) . . . . ?
C22 C21 C26 C25 -0.4(6) . . . . ?
N4 C21 C26 C25 -179.7(3) . . . . ?
C24 C25 C26 C21 1.2(6) . . . . ?
C36 C31 C32 C35 -14.5(4) . . . . ?
C45 C31 C32 C35 -160.6(3) . . . . ?
C33 C31 C32 C35 95.6(3) . . . . ?
C36 C31 C32 C33 -110.1(3) . . . . ?
C45 C31 C32 C33 103.8(3) . . . . ?
C35 C32 C33 C34 3.4(3) . . . . ?
C31 C32 C33 C34 112.6(3) . . . . ?
C35 C32 C33 C31 -109.2(3) . . . . ?
C36 C31 C33 C34 16.7(4) . . . . ?
C45 C31 C33 C34 159.0(3) . . . . ?
C32 C31 C33 C34 -92.9(3) . . . . ?
C36 C31 C33 C32 109.6(3) . . . . ?
C45 C31 C33 C32 -108.1(3) . . . . ?
C32 C33 C34 O34 173.2(3) . . . . ?
C31 C33 C34 O34 -122.9(4) . . . . ?
C32 C33 C34 N34 -6.8(3) . . . . ?
C31 C33 C34 N34 57.1(4) . . . . ?
O34 C34 N34 C35 -172.0(3) . . . . ?
C33 C34 N34 C35 8.0(3) . . . . ?
O34 C34 N34 C51 6.0(5) . . . . ?
C33 C34 N34 C51 -174.0(3) . . . . ?
C34 N34 C35 O36 174.5(3) . . . . ?
C51 N34 C35 O36 -3.5(5) . . . . ?
C34 N34 C35 C32 -5.8(3) . . . . ?
C51 N34 C35 C32 176.2(3) . . . . ?
C33 C32 C35 O36 -179.1(3) . . . . ?
C31 C32 C35 O36 116.2(4) . . . . ?
C33 C32 C35 N34 1.2(3) . . . . ?
C31 C32 C35 N34 -63.6(3) . . . . ?
C45 C31 C36 C41 -97.4(3) . . . . ?
C32 C31 C36 C41 115.4(3) . . . . ?
C33 C31 C36 C41 45.3(4) . . . . ?
C45 C31 C36 C37 76.0(4) . . . . ?
C32 C31 C36 C37 -71.2(4) . . . . ?
C33 C31 C36 C37 -141.4(3) . . . . ?
C41 C36 C37 C38 -2.9(5) . . . . ?
C31 C36 C37 C38 -176.3(3) . . . . ?
C41 C36 C37 C42 173.8(3) . . . . ?
C31 C36 C37 C42 0.4(5) . . . . ?
C36 C37 C38 C39 2.0(6) . . . . ?
C42 C37 C38 C39 -174.7(4) . . . . ?
C37 C38 C39 C40 -0.5(6) . . . . ?
C38 C39 C40 C41 0.0(6) . . . . ?
C39 C40 C41 C36 -1.0(5) . . . . ?
C37 C36 C41 C40 2.5(5) . . . . ?
C31 C36 C41 C40 176.0(3) . . . . ?
C38 C37 C42 S42 81.5(4) . . . . ?
C36 C37 C42 S42 -95.2(3) . . . . ?
C38 C37 C42 S43 -42.2(4) . . . . ?
C36 C37 C42 S43 141.1(3) . . . . ?
C37 C42 S42 C43 -103.8(3) . . . . ?
S43 C42 S42 C43 23.0(3) . . . . ?
C37 C42 S42 C43B -134.3(8) . . . . ?
S43 C42 S42 C43B -7.6(8) . . . . ?
C42 S42 C43 C44 -39.7(4) . . . . ?
C42 S42 C43B C44 21.2(16) . . . . ?
C37 C42 S43 C44 122.8(3) . . . . ?
S42 C42 S43 C44 -3.2(3) . . . . ?
S42 C43B C44 S43 -26.8(18) . . . . ?
S42 C43 C44 S43 42.0(5) . . . . ?
C42 S43 C44 C43B 18.7(12) . . . . ?
C42 S43 C44 C43 -22.7(4) . . . . ?
C36 C31 C45 C46 35.8(4) . . . . ?
C32 C31 C45 C46 -175.7(3) . . . . ?
C33 C31 C45 C46 -109.3(3) . . . . ?
C36 C31 C45 C50 -143.6(3) . . . . ?
C32 C31 C45 C50 4.9(4) . . . . ?
C33 C31 C45 C50 71.2(4) . . . . ?
C50 C45 C46 C47 0.5(5) . . . . ?
C31 C45 C46 C47 -179.0(3) . . . . ?
C45 C46 C47 C48 0.0(6) . . . . ?
C46 C47 C48 C49 -0.6(6) . . . . ?
C47 C48 C49 C50 0.6(6) . . . . ?
C48 C49 C50 C45 -0.1(6) . . . . ?
C46 C45 C50 C49 -0.5(5) . . . . ?
C31 C45 C50 C49 178.9(3) . . . . ?
C34 N34 C51 C52 -99.5(4) . . . . ?
C35 N34 C51 C52 78.2(4) . . . . ?
C34 N34 C51 C56 81.7(4) . . . . ?
C35 N34 C51 C56 -100.6(4) . . . . ?
C56 C51 C52 C53 -0.4(5) . . . . ?
N34 C51 C52 C53 -179.2(3) . . . . ?
C51 C52 C53 C54 0.6(5) . . . . ?
C52 C53 C54 C55 -0.1(6) . . . . ?
C53 C54 C55 C56 -0.7(6) . . . . ?
C52 C51 C56 C55 -0.3(6) . . . . ?
N34 C51 C56 C55 178.5(3) . . . . ?
C54 C55 C56 C51 0.9(6) . . . . ?
C75 C61 C62 C65 -163.7(3) . . . . ?
C66 C61 C62 C65 -14.9(4) . . . . ?
C63 C61 C62 C65 95.3(3) . . . . ?
C75 C61 C62 C63 101.0(3) . . . . ?
C66 C61 C62 C63 -110.2(3) . . . . ?
C65 C62 C63 C64 3.8(3) . . . . ?
C61 C62 C63 C64 112.8(3) . . . . ?
C65 C62 C63 C61 -109.0(3) . . . . ?
C75 C61 C63 C64 157.0(3) . . . . ?
C66 C61 C63 C64 14.2(4) . . . . ?
C62 C61 C63 C64 -93.4(3) . . . . ?
C75 C61 C63 C62 -109.5(3) . . . . ?
C66 C61 C63 C62 107.7(3) . . . . ?
C62 C63 C64 O64 174.5(3) . . . . ?
C61 C63 C64 O64 -121.8(4) . . . . ?
C62 C63 C64 N64 -5.5(3) . . . . ?
C61 C63 C64 N64 58.2(3) . . . . ?
O64 C64 N64 C65 -174.8(3) . . . . ?
C63 C64 N64 C65 5.1(3) . . . . ?
O64 C64 N64 C81 12.5(5) . . . . ?
C63 C64 N64 C81 -167.6(3) . . . . ?
C64 N64 C65 O65 178.1(3) . . . . ?
C81 N64 C65 O65 -9.3(5) . . . . ?
C64 N64 C65 C62 -2.6(3) . . . . ?
C81 N64 C65 C62 170.0(3) . . . . ?
C63 C62 C65 O65 178.4(3) . . . . ?
C61 C62 C65 O65 113.3(4) . . . . ?
C63 C62 C65 N64 -0.9(3) . . . . ?
C61 C62 C65 N64 -66.0(3) . . . . ?
C75 C61 C66 C71 -95.6(3) . . . . ?
C62 C61 C66 C71 115.2(3) . . . . ?
C63 C61 C66 C71 46.0(4) . . . . ?
C75 C61 C66 C67 83.8(4) . . . . ?
C62 C61 C66 C67 -65.4(4) . . . . ?
C63 C61 C66 C67 -134.6(3) . . . . ?
C71 C66 C67 C68 -1.8(5) . . . . ?
C61 C66 C67 C68 178.8(3) . . . . ?
C71 C66 C67 C72 174.5(3) . . . . ?
C61 C66 C67 C72 -4.9(5) . . . . ?
C66 C67 C68 C69 0.2(5) . . . . ?
C72 C67 C68 C69 -176.2(3) . . . . ?
C67 C68 C69 C70 0.9(6) . . . . ?
C68 C69 C70 C71 -0.5(6) . . . . ?
C69 C70 C71 C66 -1.0(6) . . . . ?
C67 C66 C71 C70 2.2(5) . . . . ?
C61 C66 C71 C70 -178.4(3) . . . . ?
C68 C67 C72 S73 71.9(3) . . . . ?
C66 C67 C72 S73 -104.3(3) . . . . ?
C68 C67 C72 S72 -48.8(4) . . . . ?
C66 C67 C72 S72 134.9(3) . . . . ?
C67 C72 S72 C74 115.4(3) . . . . ?
S73 C72 S72 C74 -5.8(2) . . . . ?
C74 C73 S73 C72 42.6(3) . . . . ?
C67 C72 S73 C73 -143.5(2) . . . . ?
S72 C72 S73 C73 -18.6(2) . . . . ?
S73 C73 C74 S72 -51.1(3) . . . . ?
C72 S72 C74 C73 34.7(3) . . . . ?
C66 C61 C75 C80 -133.2(3) . . . . ?
C62 C61 C75 C80 16.5(4) . . . . ?
C63 C61 C75 C80 82.2(4) . . . . ?
C66 C61 C75 C76 51.1(4) . . . . ?
C62 C61 C75 C76 -159.2(3) . . . . ?
C63 C61 C75 C76 -93.5(3) . . . . ?
C80 C75 C76 C77 -0.1(5) . . . . ?
C61 C75 C76 C77 175.8(3) . . . . ?
C75 C76 C77 C78 0.1(5) . . . . ?
C76 C77 C78 C79 -0.3(5) . . . . ?
C77 C78 C79 C80 0.3(5) . . . . ?
C76 C75 C80 C79 0.1(5) . . . . ?
C61 C75 C80 C79 -175.6(3) . . . . ?
C78 C79 C80 C75 -0.2(5) . . . . ?
C65 N64 C81 C86 130.5(3) . . . . ?
C64 N64 C81 C86 -57.7(4) . . . . ?
C65 N64 C81 C82 -51.9(4) . . . . ?
C64 N64 C81 C82 119.9(3) . . . . ?
C86 C81 C82 C83 -0.4(5) . . . . ?
N64 C81 C82 C83 -177.9(3) . . . . ?
C81 C82 C83 C84 1.5(6) . . . . ?
C82 C83 C84 C85 -1.4(6) . . . . ?
C83 C84 C85 C86 0.2(5) . . . . ?
C82 C81 C86 C85 -0.8(5) . . . . ?
N64 C81 C86 C85 176.8(3) . . . . ?
C84 C85 C86 C81 0.9(5) . . . . ?
C105 C91 C92 C95 -161.2(3) . . . . ?
C96 C91 C92 C95 -14.7(4) . . . . ?
C93 C91 C92 C95 95.2(3) . . . . ?
C105 C91 C92 C93 103.5(3) . . . . ?
C96 C91 C92 C93 -109.9(3) . . . . ?
C95 C92 C93 C94 5.5(3) . . . . ?
C91 C92 C93 C94 113.6(3) . . . . ?
C95 C92 C93 C91 -108.1(3) . . . . ?
C105 C91 C93 C94 159.3(3) . . . . ?
C96 C91 C93 C94 13.6(4) . . . . ?
C92 C91 C93 C94 -93.4(3) . . . . ?
C105 C91 C93 C92 -107.2(3) . . . . ?
C96 C91 C93 C92 107.0(3) . . . . ?
C92 C93 C94 O94 171.6(3) . . . . ?
C91 C93 C94 O94 -124.1(3) . . . . ?
C92 C93 C94 N94 -7.5(3) . . . . ?
C91 C93 C94 N94 56.8(3) . . . . ?
O94 C94 N94 C95 -172.4(3) . . . . ?
C93 C94 N94 C95 6.8(3) . . . . ?
O94 C94 N94 C111 13.4(5) . . . . ?
C93 C94 N94 C111 -167.4(3) . . . . ?
C94 N94 C95 O95 176.9(3) . . . . ?
C111 N94 C95 O95 -9.0(5) . . . . ?
C94 N94 C95 C92 -3.2(3) . . . . ?
C111 N94 C95 C92 171.0(3) . . . . ?
C93 C92 C95 O95 178.3(3) . . . . ?
C91 C92 C95 O95 113.7(4) . . . . ?
C93 C92 C95 N94 -1.6(3) . . . . ?
C91 C92 C95 N94 -66.2(3) . . . . ?
C105 C91 C96 C101 -101.6(3) . . . . ?
C92 C91 C96 C101 112.1(3) . . . . ?
C93 C91 C96 C101 43.4(4) . . . . ?
C105 C91 C96 C97 76.9(4) . . . . ?
C92 C91 C96 C97 -69.5(4) . . . . ?
C93 C91 C96 C97 -138.2(3) . . . . ?
C101 C96 C97 C98 -2.0(5) . . . . ?
C91 C96 C97 C98 179.5(3) . . . . ?
C101 C96 C97 C102 175.8(3) . . . . ?
C91 C96 C97 C102 -2.6(5) . . . . ?
C96 C97 C98 C99 0.4(5) . . . . ?
C102 C97 C98 C99 -177.5(3) . . . . ?
C97 C98 C99 C100 1.1(5) . . . . ?
C98 C99 C100 C101 -0.9(5) . . . . ?
C99 C100 C101 C96 -0.7(5) . . . . ?
C97 C96 C101 C100 2.2(5) . . . . ?
C91 C96 C101 C100 -179.3(3) . . . . ?
C98 C97 C102 S103 -45.4(4) . . . . ?
C96 C97 C102 S103 136.8(3) . . . . ?
C98 C97 C102 S102 76.7(3) . . . . ?
C96 C97 C102 S102 -101.2(3) . . . . ?
C97 C102 S102 C103 -135.1(2) . . . . ?
S103 C102 S102 C103 -8.9(2) . . . . ?
C102 S102 C103 C104 34.6(3) . . . . ?
C97 C102 S103 C104 109.1(3) . . . . ?
S102 C102 S103 C104 -13.5(2) . . . . ?
S102 C103 C104 S103 -47.5(3) . . . . ?
C102 S103 C104 C103 37.3(3) . . . . ?
C96 C91 C105 C106 -170.9(3) . . . . ?
C92 C91 C105 C106 -23.8(4) . . . . ?
C93 C91 C105 C106 42.1(4) . . . . ?
C96 C91 C105 C110 11.9(4) . . . . ?
C92 C91 C105 C110 159.0(3) . . . . ?
C93 C91 C105 C110 -135.1(3) . . . . ?
C110 C105 C106 C107 0.4(5) . . . . ?
C91 C105 C106 C107 -176.9(3) . . . . ?
C105 C106 C107 C108 -0.4(5) . . . . ?
C106 C107 C108 C109 0.2(5) . . . . ?
C107 C108 C109 C110 0.2(5) . . . . ?
C108 C109 C110 C105 -0.2(5) . . . . ?
C106 C105 C110 C109 -0.1(5) . . . . ?
C91 C105 C110 C109 177.3(3) . . . . ?
C95 N94 C111 C116 121.6(3) . . . . ?
C94 N94 C111 C116 -64.8(4) . . . . ?
C95 N94 C111 C112 -59.4(4) . . . . ?
C94 N94 C111 C112 114.2(3) . . . . ?
C116 C111 C112 C113 -1.4(5) . . . . ?
N94 C111 C112 C113 179.7(3) . . . . ?
C111 C112 C113 C114 0.5(5) . . . . ?
C112 C113 C114 C115 0.3(5) . . . . ?
C113 C114 C115 C116 -0.3(5) . . . . ?
C112 C111 C116 C115 1.4(5) . . . . ?
N94 C111 C116 C115 -179.6(3) . . . . ?
C114 C115 C116 C111 -0.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22 O4 0.95 2.57 3.397(4) 146 2_656 yes
C43 H43A O95 0.99 2.43 3.300(6) 147. . yes
C52 H52 O5 0.95 2.51 3.239(4) 133. 1_565 yes
C63 H63 O94 1.00 2.40 3.355(4) 160. 2_667 yes
C73 H73A S102 0.99 3.01 3.785(4) 136. 1_565 yes
C116 H116 O65 0.95 2.27 3.097(4) 144. 1_655 yes
O121 H12A O34 0.842(5) 2.17(5) 2.925(10) 148(9) . yes
O122 H12C O34 0.842(5) 2.16(8) 2.872(13) 143(12) . yes

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.061

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF3006F2MI
_database_code_depnum_ccdc_archive 'CCDC 2087135'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6220(11)
_cell_length_b                   9.9052(9)
_cell_length_c                   13.1752(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.220(3)
_cell_angle_gamma                90
_cell_volume                     1637.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.59

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.197
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8651
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14062
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3764
_reflns_number_gt                3371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
19 January, 2021
JF3006  JMR-1-156

A colorless block with approximate orthogonal dimensions 0.197 x 0.228 x 0.339mm3 was placed and optically centered on the Bruker1 Venture Dual source Kappa Photon100 diffractometer at â\/E?173Â°C(100K).  Indexing of the unit cell used a random set of reflections collected from three series of 0.5Â° wide ï?.-scans, 5 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Data were collected [MoKï??] with 0.3Â° wide scans, variable time per frame dependent upon detector 2ï?+- angle and varying Ï? and omega angles such that nearly all unique reflections were collected at least once.  The crystal to detector distance was 65.00mm, thus providing a complete sphere of data to 2ï?+-max=55.26Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7 with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint1 and absorption using Blessingâ\/E?s method and merged as incorporated with the program Sadabs2,3. The SHELXTL4 program package was implemented to determine the probable space group and set up the initial files. System symmetry, systematic absences and intensity statistics indicated the centrosymmetric monoclinic space group P21/n (no. 14). The structure was determined by direct methods with the location of nearly all of the non-hydrogen atoms for the molecule of using the program XT5. The structure was refined with XL6. The 31994 data collected were merged for identical indices to 14062 reflections and then for least squares refinement to 3764 unique data [R(int)=0.0279]. Non-hydrogen atoms were refined anisotropically. Hydrogen atoms were idealized throughout the final refinement. The final structure was refined to convergence with R(F)=5.06%, wR(F2)=12.23%, GOF=1.030 for all 3764 unique reflections [R(F)=4.59, wR(F2)=11.76% for those 3371 data with Fo > 4ï?³(Fo)]. The final difference-Fourier map was featureless indicating that the structure is both correct and complete. 

References:

1.	Bruker (2019) APEX3 (Version 2019.1) and (2016) SAINT (Version 8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.
2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193) for the Dual Source X-ray diffractometer.





;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.7573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65275(9) 0.71847(12) 0.59488(9) 0.0186(3) Uani 1 1 d . . . . .
O1 O 0.58073(7) 0.70099(9) 0.50445(7) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.70157(9) 0.57939(12) 0.62400(9) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.756320 0.590607 0.684186 0.022 Uiso 1 1 calc R U . . .
O2 O 0.73379(7) 0.80799(9) 0.57026(7) 0.0226(2) Uani 1 1 d . . . . .
C3 C 0.61186(9) 0.48715(12) 0.65472(9) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.549067 0.494933 0.601836 0.022 Uiso 1 1 calc R U . . .
C4 C 0.57896(9) 0.53726(12) 0.75806(9) 0.0187(2) Uani 1 1 d . . . . .
H4 H 0.639476 0.517953 0.811550 0.022 Uiso 1 1 calc R U . . .
C5 C 0.56099(9) 0.68996(12) 0.75615(9) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.59743(9) 0.77481(12) 0.68259(9) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.58350(10) 0.91452(12) 0.68879(10) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.608837 0.971729 0.638822 0.026 Uiso 1 1 calc R U . . .
C8 C 0.53297(10) 0.97024(13) 0.76731(10) 0.0245(3) Uani 1 1 d . . . . .
H8 H 0.523112 1.065148 0.770784 0.029 Uiso 1 1 calc R U . . .
C9 C 0.49685(10) 0.88646(14) 0.84087(10) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.462622 0.924085 0.895078 0.030 Uiso 1 1 calc R U . . .
C10 C 0.51081(10) 0.74773(13) 0.83508(10) 0.0234(3) Uani 1 1 d . . . . .
H10 H 0.485830 0.691145 0.885621 0.028 Uiso 1 1 calc R U . . .
C11 C 0.59850(12) 0.81063(13) 0.43674(10) 0.0274(3) Uani 1 1 d . . . . .
H11A H 0.554929 0.890382 0.450359 0.033 Uiso 1 1 calc R U . . .
H11B H 0.582213 0.783620 0.364389 0.033 Uiso 1 1 calc R U . . .
C12 C 0.71605(12) 0.83875(15) 0.46259(10) 0.0298(3) Uani 1 1 d . . . . .
H12A H 0.759665 0.779980 0.422750 0.036 Uiso 1 1 calc R U . . .
H12B H 0.732885 0.934350 0.449401 0.036 Uiso 1 1 calc R U . . .
C13 C 0.75362(10) 0.52470(12) 0.53845(10) 0.0216(3) Uani 1 1 d . . . . .
N13 N 0.79432(10) 0.48171(12) 0.47246(9) 0.0290(3) Uani 1 1 d . . . . .
C14 C 0.64584(10) 0.34455(13) 0.66174(9) 0.0214(3) Uani 1 1 d . . . . .
N14 N 0.67131(9) 0.23392(11) 0.66604(9) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.48284(10) 0.45908(12) 0.78596(9) 0.0201(3) Uani 1 1 d . . . . .
C16 C 0.38174(10) 0.48494(13) 0.73630(10) 0.0241(3) Uani 1 1 d . . . . .
H16 H 0.372866 0.552516 0.684915 0.029 Uiso 1 1 calc R U . . .
C17 C 0.29374(11) 0.41274(14) 0.76128(10) 0.0276(3) Uani 1 1 d . . . . .
H17 H 0.224944 0.431639 0.727603 0.033 Uiso 1 1 calc R U . . .
C18 C 0.30673(12) 0.31268(15) 0.83579(11) 0.0299(3) Uani 1 1 d . . . . .
H18 H 0.246705 0.263350 0.853145 0.036 Uiso 1 1 calc R U . . .
C19 C 0.40713(12) 0.28503(15) 0.88462(11) 0.0311(3) Uani 1 1 d . . . . .
H19 H 0.416040 0.216003 0.934878 0.037 Uiso 1 1 calc R U . . .
C20 C 0.49514(11) 0.35837(13) 0.86012(10) 0.0257(3) Uani 1 1 d . . . . .
H20 H 0.563807 0.339594 0.894146 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.4176(14) . ?
C1 O1 1.4287(15) . ?
C1 C6 1.5197(17) . ?
C1 C2 1.5406(16) . ?
O1 C11 1.4384(15) . ?
C2 C13 1.4683(17) . ?
C2 C3 1.5428(16) . ?
C2 H2 1.0000 . ?
O2 C12 1.4445(16) . ?
C3 C14 1.4762(17) . ?
C3 C4 1.5476(16) . ?
C3 H3 1.0000 . ?
C4 C15 1.5177(16) . ?
C4 C5 1.5292(16) . ?
C4 H4 1.0000 . ?
C5 C10 1.3975(17) . ?
C5 C6 1.3978(17) . ?
C6 C7 1.3984(17) . ?
C7 C8 1.3874(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3886(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.512(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N13 1.1393(17) . ?
C14 N14 1.1416(17) . ?
C15 C16 1.3931(18) . ?
C15 C20 1.3932(17) . ?
C16 C17 1.3902(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3941(19) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 107.14(9) . . ?
O2 C1 C6 110.28(10) . . ?
O1 C1 C6 112.05(10) . . ?
O2 C1 C2 109.71(9) . . ?
O1 C1 C2 107.49(9) . . ?
C6 C1 C2 110.08(10) . . ?
C1 O1 C11 107.32(9) . . ?
C13 C2 C1 109.81(10) . . ?
C13 C2 C3 112.65(10) . . ?
C1 C2 C3 108.05(9) . . ?
C13 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 O2 C12 108.52(9) . . ?
C14 C3 C2 111.50(10) . . ?
C14 C3 C4 110.83(10) . . ?
C2 C3 C4 108.39(9) . . ?
C14 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C15 C4 C5 112.81(10) . . ?
C15 C4 C3 110.31(10) . . ?
C5 C4 C3 110.87(10) . . ?
C15 C4 H4 107.5 . . ?
C5 C4 H4 107.5 . . ?
C3 C4 H4 107.5 . . ?
C10 C5 C6 118.65(11) . . ?
C10 C5 C4 118.11(11) . . ?
C6 C5 C4 123.15(11) . . ?
C5 C6 C7 120.11(11) . . ?
C5 C6 C1 121.28(11) . . ?
C7 C6 C1 118.61(11) . . ?
C8 C7 C6 120.54(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.63(12) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.96(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.10(12) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
O1 C11 C12 102.39(10) . . ?
O1 C11 H11A 111.3 . . ?
C12 C11 H11A 111.3 . . ?
O1 C11 H11B 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
O2 C12 C11 103.08(10) . . ?
O2 C12 H12A 111.1 . . ?
C11 C12 H12A 111.1 . . ?
O2 C12 H12B 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
N13 C13 C2 179.59(14) . . ?
N14 C14 C3 179.13(14) . . ?
C16 C15 C20 119.20(12) . . ?
C16 C15 C4 120.53(11) . . ?
C20 C15 C4 120.25(11) . . ?
C17 C16 C15 120.59(12) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.81(13) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.01(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.09(13) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.29(13) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 C11 -18.16(12) . . . . ?
C6 C1 O1 C11 102.93(11) . . . . ?
C2 C1 O1 C11 -136.01(10) . . . . ?
O2 C1 C2 C13 -59.23(12) . . . . ?
O1 C1 C2 C13 56.94(12) . . . . ?
C6 C1 C2 C13 179.23(10) . . . . ?
O2 C1 C2 C3 177.55(9) . . . . ?
O1 C1 C2 C3 -66.28(11) . . . . ?
C6 C1 C2 C3 56.01(12) . . . . ?
O1 C1 O2 C12 -3.91(13) . . . . ?
C6 C1 O2 C12 -126.11(11) . . . . ?
C2 C1 O2 C12 112.48(11) . . . . ?
C13 C2 C3 C14 45.92(13) . . . . ?
C1 C2 C3 C14 167.40(10) . . . . ?
C13 C2 C3 C4 168.19(10) . . . . ?
C1 C2 C3 C4 -70.33(12) . . . . ?
C14 C3 C4 C15 -63.40(13) . . . . ?
C2 C3 C4 C15 173.92(9) . . . . ?
C14 C3 C4 C5 170.90(10) . . . . ?
C2 C3 C4 C5 48.23(12) . . . . ?
C15 C4 C5 C10 43.21(15) . . . . ?
C3 C4 C5 C10 167.50(10) . . . . ?
C15 C4 C5 C6 -140.37(12) . . . . ?
C3 C4 C5 C6 -16.09(16) . . . . ?
C10 C5 C6 C7 0.04(17) . . . . ?
C4 C5 C6 C7 -176.35(11) . . . . ?
C10 C5 C6 C1 179.94(11) . . . . ?
C4 C5 C6 C1 3.54(17) . . . . ?
O2 C1 C6 C5 -144.73(11) . . . . ?
O1 C1 C6 C5 96.01(13) . . . . ?
C2 C1 C6 C5 -23.54(15) . . . . ?
O2 C1 C6 C7 35.17(15) . . . . ?
O1 C1 C6 C7 -84.09(13) . . . . ?
C2 C1 C6 C7 156.36(11) . . . . ?
C5 C6 C7 C8 -0.41(18) . . . . ?
C1 C6 C7 C8 179.69(11) . . . . ?
C6 C7 C8 C9 0.60(19) . . . . ?
C7 C8 C9 C10 -0.43(19) . . . . ?
C8 C9 C10 C5 0.06(19) . . . . ?
C6 C5 C10 C9 0.13(18) . . . . ?
C4 C5 C10 C9 176.71(11) . . . . ?
C1 O1 C11 C12 31.57(13) . . . . ?
C1 O2 C12 C11 22.95(13) . . . . ?
O1 C11 C12 O2 -32.89(13) . . . . ?
C5 C4 C15 C16 49.73(15) . . . . ?
C3 C4 C15 C16 -74.85(14) . . . . ?
C5 C4 C15 C20 -131.68(12) . . . . ?
C3 C4 C15 C20 103.73(13) . . . . ?
C20 C15 C16 C17 0.94(19) . . . . ?
C4 C15 C16 C17 179.55(12) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C16 C15 C20 C19 -0.4(2) . . . . ?
C4 C15 C20 C19 -178.97(12) . . . . ?
C18 C19 C20 C15 -0.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N14 1.00 2.52 3.4071(17) 147.6 2_656 yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF3055FMI
_database_code_depnum_ccdc_archive 'CCDC 2240749'
loop_
_audit_author_name
_audit_author_address
'James Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-02-08 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9089(3)
_cell_length_b                   21.0205(9)
_cell_length_c                   13.3410(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.0784(16)
_cell_angle_gamma                90
_cell_volume                     2205.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      33.14

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9261
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24830
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6426
_reflns_number_gt                5835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

12 August, 2021
JF3055 Mo  (JMR-II-175)

A colorless block with approximate orthogonal dimensions 0.150 x 0.302 x 0.401mm3 was placed and optically centered on the Bruker1 Venture Dual source Kappa Photon2 diffractometer at â\/E?83Â°C(190K).  Indexing of the unit cell used a random set of reflections collected from three series of 0.5Â° wide ï?.-scans, 5 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Data were collected [MoKï??] with 0.3Â° wide scans, variable time per frame dependent upon detector 2ï?+- angle and varying Ï? and omega angles such that nearly all unique reflections were collected at least once.  The crystal to detector distance was 70.00mm, thus providing a complete sphere of data to 2ï?+-max=66.32Â°.


Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7 with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint1 and absorption using Blessingâ\/E?s method and merged as incorporated with the program Sadabs2,3. The SHELXTL4 program package was implemented to determine the probable space group and set up the initial files. System symmetry, systematic absences and intensity statistics indicated the non-standard centrosymmetric monoclinic space group P21/n (no. 14). The structure was determined by direct methods with nearly all non-hydrogen atoms being located directly for the molecule using the program XT5. The structure was refined with XL6. The 117873 data collected were merged, based upon identical indices to 32805 data, then truncated to 24830 (60Â°) and then merged for least squares refinement to 6426 unique data [R(int)=0.0166]. All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were idealized initially and then allowed to refine freely throughout the final refinement stage. The final structure was refined to convergence with R(F)=4.13%, wR(F2)=9.78%, GOF=1.039 for all 6426 unique reflections [R(F)=3.73, wR(F2)=9.45% for those 5835 data with Fo > 4ï?³(Fo)]. The final difference-Fourier map was featureless indicating that the structure is both correct and complete.  An empirical correction for extinction was found to be less than 2sigma and therefore not applied.  

References:

1.	Bruker (2019) APEX3 (Version 2019.0) and (2016) SAINT (Version 8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.
2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen: GÃ?ttingen, Germany.

James C. Fettinger, PhD

Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193) for the Dual Source X-ray diffractometer.


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.9811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6426
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54359(11) 0.34190(4) 0.21727(6) 0.01282(15) Uani 1 1 d . . . . .
C2 C 0.52303(12) 0.32736(4) 0.32769(7) 0.01478(16) Uani 1 1 d . . . . .
H2 H 0.4117(17) 0.3199(6) 0.3471(10) 0.019(3) Uiso 1 1 d . . . . .
C3 C 0.61709(12) 0.28071(4) 0.26830(7) 0.01497(16) Uani 1 1 d . . . . .
H3 H 0.5695(17) 0.2408(7) 0.2443(10) 0.022(3) Uiso 1 1 d . . . . .
C4 C 0.79879(12) 0.28245(4) 0.31259(7) 0.01598(16) Uani 1 1 d . . . . .
N4 N 0.81297(10) 0.32964(4) 0.38691(6) 0.01592(15) Uani 1 1 d . . . . .
O4 O 0.91440(9) 0.24964(3) 0.29000(5) 0.02044(15) Uani 1 1 d . . . . .
C5 C 0.65556(12) 0.35679(4) 0.40190(7) 0.01625(17) Uani 1 1 d . . . . .
O5 O 0.63527(10) 0.39675(4) 0.46448(5) 0.02258(15) Uani 1 1 d . . . . .
C6 C 0.65809(11) 0.39589(4) 0.19423(7) 0.01348(16) Uani 1 1 d . . . . .
C7 C 0.80746(12) 0.38394(4) 0.15027(7) 0.01603(17) Uani 1 1 d . . . . .
H7 H 0.8375(17) 0.3399(7) 0.1353(10) 0.021(3) Uiso 1 1 d . . . . .
C8 C 0.91393(12) 0.43339(5) 0.12761(8) 0.01939(18) Uani 1 1 d . . . . .
H8 H 1.0175(18) 0.4246(7) 0.0969(10) 0.022(3) Uiso 1 1 d . . . . .
C9 C 0.87133(12) 0.49551(5) 0.14977(8) 0.02066(19) Uani 1 1 d . . . . .
H9 H 0.9439(19) 0.5306(7) 0.1348(11) 0.026(3) Uiso 1 1 d . . . . .
C10 C 0.72306(12) 0.50786(4) 0.19397(8) 0.01853(18) Uani 1 1 d . . . . .
H10 H 0.6928(19) 0.5510(7) 0.2109(11) 0.028(4) Uiso 1 1 d . . . . .
C11 C 0.61306(11) 0.45887(4) 0.21516(7) 0.01466(16) Uani 1 1 d . . . . .
C12 C 0.44916(12) 0.47335(4) 0.26007(7) 0.01639(17) Uani 1 1 d . . . . .
H12A H 0.3584(18) 0.4441(7) 0.2289(10) 0.020(3) Uiso 1 1 d . . . . .
H12B H 0.4631(17) 0.4643(7) 0.3331(11) 0.021(3) Uiso 1 1 d . . . . .
N12 N 0.39610(10) 0.53971(4) 0.24777(6) 0.01460(14) Uani 1 1 d . . . . .
C13 C 0.25854(13) 0.55237(5) 0.31055(7) 0.01798(17) Uani 1 1 d . . . . .
H13A H 0.2992(17) 0.5451(7) 0.3803(11) 0.022(3) Uiso 1 1 d . . . . .
H13B H 0.1569(19) 0.5241(7) 0.2921(11) 0.025(3) Uiso 1 1 d . . . . .
C14 C 0.20281(15) 0.62109(5) 0.29917(8) 0.0241(2) Uani 1 1 d . . . . .
H14A H 0.1060(19) 0.6289(7) 0.3378(12) 0.029(4) Uiso 1 1 d . . . . .
H14B H 0.303(2) 0.6493(8) 0.3241(12) 0.034(4) Uiso 1 1 d . . . . .
O14 O 0.14747(10) 0.63672(4) 0.19627(6) 0.02307(16) Uani 1 1 d . . . . .
C15 C 0.28198(13) 0.62415(5) 0.13518(8) 0.02060(19) Uani 1 1 d . . . . .
H15A H 0.3809(18) 0.6521(7) 0.1567(11) 0.024(3) Uiso 1 1 d . . . . .
H15B H 0.2371(18) 0.6352(7) 0.0669(11) 0.024(3) Uiso 1 1 d . . . . .
C16 C 0.33618(12) 0.55486(4) 0.14276(7) 0.01629(17) Uani 1 1 d . . . . .
H16A H 0.2394(18) 0.5259(7) 0.1156(11) 0.023(3) Uiso 1 1 d . . . . .
H16B H 0.4299(17) 0.5464(6) 0.1002(10) 0.017(3) Uiso 1 1 d . . . . .
C17 C 0.39086(11) 0.33035(4) 0.14178(6) 0.01353(16) Uani 1 1 d . . . . .
C18 C 0.26423(12) 0.28695(4) 0.16088(7) 0.01703(17) Uani 1 1 d . . . . .
H18 H 0.2692(18) 0.2655(7) 0.2243(11) 0.026(3) Uiso 1 1 d . . . . .
C19 C 0.13023(12) 0.27386(5) 0.08744(8) 0.01950(18) Uani 1 1 d . . . . .
H19 H 0.044(2) 0.2432(8) 0.1023(12) 0.034(4) Uiso 1 1 d . . . . .
C20 C 0.11908(12) 0.30404(5) -0.00556(8) 0.01980(18) Uani 1 1 d . . . . .
H20 H 0.0248(19) 0.2950(7) -0.0549(11) 0.027(4) Uiso 1 1 d . . . . .
C21 C 0.24347(13) 0.34763(5) -0.02511(7) 0.01958(18) Uani 1 1 d . . . . .
H21 H 0.239(2) 0.3681(7) -0.0895(12) 0.032(4) Uiso 1 1 d . . . . .
C22 C 0.37837(12) 0.36080(4) 0.04811(7) 0.01690(17) Uani 1 1 d . . . . .
H22 H 0.4638(17) 0.3911(6) 0.0329(10) 0.019(3) Uiso 1 1 d . . . . .
C23 C 0.96892(12) 0.34774(5) 0.44407(7) 0.01668(17) Uani 1 1 d . . . . .
C24 C 1.02314(14) 0.41052(5) 0.44235(8) 0.0242(2) Uani 1 1 d . . . . .
H24 H 0.954(2) 0.4424(8) 0.3992(12) 0.033(4) Uiso 1 1 d . . . . .
C25 C 1.16990(15) 0.42833(6) 0.50298(9) 0.0291(2) Uani 1 1 d . . . . .
H25 H 1.210(2) 0.4713(9) 0.5034(13) 0.045(5) Uiso 1 1 d . . . . .
C26 C 1.26169(13) 0.38373(6) 0.56318(8) 0.0266(2) Uani 1 1 d . . . . .
H26 H 1.362(2) 0.3974(8) 0.6052(12) 0.034(4) Uiso 1 1 d . . . . .
C27 C 1.20698(13) 0.32117(6) 0.56267(8) 0.0245(2) Uani 1 1 d . . . . .
H27 H 1.270(2) 0.2899(7) 0.6049(12) 0.031(4) Uiso 1 1 d . . . . .
C28 C 1.06001(12) 0.30253(5) 0.50320(7) 0.01990(18) Uani 1 1 d . . . . .
H28 H 1.0189(19) 0.2587(7) 0.5023(11) 0.027(3) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.5038(12) . ?
C1 C17 1.5082(12) . ?
C1 C2 1.5299(12) . ?
C1 C3 1.5401(12) . ?
C2 C5 1.4973(13) . ?
C2 C3 1.5058(13) . ?
C2 H2 0.956(14) . ?
C3 C4 1.4953(13) . ?
C3 H3 0.960(14) . ?
C4 O4 1.2088(12) . ?
C4 N4 1.3985(12) . ?
N4 C5 1.4030(12) . ?
N4 C23 1.4312(12) . ?
C5 O5 1.2068(12) . ?
C6 C7 1.3962(12) . ?
C6 C11 1.4067(12) . ?
C7 C8 1.3910(13) . ?
C7 H7 0.982(14) . ?
C8 C9 1.3884(14) . ?
C8 H8 0.971(14) . ?
C9 C10 1.3915(14) . ?
C9 H9 0.967(15) . ?
C10 C11 1.3961(12) . ?
C10 H10 0.970(15) . ?
C11 C12 1.5154(12) . ?
C12 N12 1.4609(11) . ?
C12 H12A 1.001(14) . ?
C12 H12B 0.987(14) . ?
N12 C16 1.4657(12) . ?
N12 C13 1.4659(12) . ?
C13 C14 1.5132(14) . ?
C13 H13A 0.963(14) . ?
C13 H13B 1.008(15) . ?
C14 O14 1.4342(12) . ?
C14 H14A 0.981(15) . ?
C14 H14B 1.014(16) . ?
O14 C15 1.4316(12) . ?
C15 C16 1.5186(14) . ?
C15 H15A 0.996(15) . ?
C15 H15B 0.970(14) . ?
C16 H16A 1.015(14) . ?
C16 H16B 0.996(13) . ?
C17 C18 1.3980(12) . ?
C17 C22 1.3983(12) . ?
C18 C19 1.3925(13) . ?
C18 H18 0.956(15) . ?
C19 C20 1.3881(14) . ?
C19 H19 0.975(16) . ?
C20 C21 1.3892(15) . ?
C20 H20 0.960(15) . ?
C21 C22 1.3959(13) . ?
C21 H21 0.958(16) . ?
C22 H22 0.965(14) . ?
C23 C28 1.3870(13) . ?
C23 C24 1.3884(14) . ?
C24 C25 1.3939(15) . ?
C24 H24 1.005(16) . ?
C25 C26 1.3883(17) . ?
C25 H25 0.956(19) . ?
C26 C27 1.3842(17) . ?
C26 H26 0.967(16) . ?
C27 C28 1.3924(14) . ?
C27 H27 0.969(16) . ?
C28 H28 0.976(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C17 116.23(7) . . ?
C6 C1 C2 118.38(7) . . ?
C17 C1 C2 116.84(7) . . ?
C6 C1 C3 120.89(7) . . ?
C17 C1 C3 113.51(7) . . ?
C2 C1 C3 58.74(6) . . ?
C5 C2 C3 105.47(7) . . ?
C5 C2 C1 114.57(7) . . ?
C3 C2 C1 60.97(6) . . ?
C5 C2 H2 119.3(8) . . ?
C3 C2 H2 123.8(8) . . ?
C1 C2 H2 119.2(8) . . ?
C4 C3 C2 106.49(7) . . ?
C4 C3 C1 117.14(7) . . ?
C2 C3 C1 60.29(6) . . ?
C4 C3 H3 118.7(8) . . ?
C2 C3 H3 123.1(8) . . ?
C1 C3 H3 117.8(8) . . ?
O4 C4 N4 125.14(9) . . ?
O4 C4 C3 127.46(9) . . ?
N4 C4 C3 107.40(8) . . ?
C4 N4 C5 112.57(8) . . ?
C4 N4 C23 124.48(8) . . ?
C5 N4 C23 122.92(8) . . ?
O5 C5 N4 124.52(9) . . ?
O5 C5 C2 127.58(9) . . ?
N4 C5 C2 107.89(8) . . ?
C7 C6 C11 119.74(8) . . ?
C7 C6 C1 120.31(8) . . ?
C11 C6 C1 119.94(8) . . ?
C8 C7 C6 121.03(9) . . ?
C8 C7 H7 119.7(8) . . ?
C6 C7 H7 119.2(8) . . ?
C9 C8 C7 119.37(9) . . ?
C9 C8 H8 120.2(8) . . ?
C7 C8 H8 120.4(8) . . ?
C8 C9 C10 120.00(9) . . ?
C8 C9 H9 120.7(9) . . ?
C10 C9 H9 119.3(9) . . ?
C9 C10 C11 121.29(9) . . ?
C9 C10 H10 120.8(9) . . ?
C11 C10 H10 117.9(9) . . ?
C10 C11 C6 118.53(8) . . ?
C10 C11 C12 120.63(8) . . ?
C6 C11 C12 120.84(8) . . ?
N12 C12 C11 113.26(7) . . ?
N12 C12 H12A 110.8(8) . . ?
C11 C12 H12A 108.6(8) . . ?
N12 C12 H12B 107.2(8) . . ?
C11 C12 H12B 109.9(8) . . ?
H12A C12 H12B 106.9(11) . . ?
C12 N12 C16 112.01(7) . . ?
C12 N12 C13 109.32(7) . . ?
C16 N12 C13 108.80(7) . . ?
N12 C13 C14 109.99(8) . . ?
N12 C13 H13A 109.3(8) . . ?
C14 C13 H13A 108.2(8) . . ?
N12 C13 H13B 112.0(8) . . ?
C14 C13 H13B 108.8(8) . . ?
H13A C13 H13B 108.5(12) . . ?
O14 C14 C13 111.77(8) . . ?
O14 C14 H14A 106.7(9) . . ?
C13 C14 H14A 110.0(9) . . ?
O14 C14 H14B 109.1(9) . . ?
C13 C14 H14B 108.5(9) . . ?
H14A C14 H14B 110.7(13) . . ?
C15 O14 C14 109.44(8) . . ?
O14 C15 C16 111.14(8) . . ?
O14 C15 H15A 109.6(8) . . ?
C16 C15 H15A 109.8(8) . . ?
O14 C15 H15B 105.7(8) . . ?
C16 C15 H15B 111.4(9) . . ?
H15A C15 H15B 109.1(12) . . ?
N12 C16 C15 109.42(8) . . ?
N12 C16 H16A 111.5(8) . . ?
C15 C16 H16A 110.8(8) . . ?
N12 C16 H16B 108.8(8) . . ?
C15 C16 H16B 110.8(8) . . ?
H16A C16 H16B 105.6(11) . . ?
C18 C17 C22 118.52(8) . . ?
C18 C17 C1 121.46(8) . . ?
C22 C17 C1 119.93(8) . . ?
C19 C18 C17 120.49(9) . . ?
C19 C18 H18 119.1(9) . . ?
C17 C18 H18 120.4(9) . . ?
C20 C19 C18 120.68(9) . . ?
C20 C19 H19 120.2(9) . . ?
C18 C19 H19 119.1(9) . . ?
C19 C20 C21 119.35(9) . . ?
C19 C20 H20 119.6(9) . . ?
C21 C20 H20 121.0(9) . . ?
C20 C21 C22 120.23(9) . . ?
C20 C21 H21 120.2(9) . . ?
C22 C21 H21 119.6(9) . . ?
C21 C22 C17 120.74(9) . . ?
C21 C22 H22 119.0(8) . . ?
C17 C22 H22 120.3(8) . . ?
C28 C23 C24 121.19(9) . . ?
C28 C23 N4 119.16(9) . . ?
C24 C23 N4 119.61(8) . . ?
C23 C24 C25 119.04(10) . . ?
C23 C24 H24 119.7(9) . . ?
C25 C24 H24 121.3(9) . . ?
C26 C25 C24 120.44(11) . . ?
C26 C25 H25 118.9(11) . . ?
C24 C25 H25 120.7(11) . . ?
C27 C26 C25 119.64(10) . . ?
C27 C26 H26 121.5(10) . . ?
C25 C26 H26 118.9(10) . . ?
C26 C27 C28 120.79(10) . . ?
C26 C27 H27 120.0(9) . . ?
C28 C27 H27 119.2(9) . . ?
C23 C28 C27 118.90(10) . . ?
C23 C28 H28 119.2(9) . . ?
C27 C28 H28 122.0(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C5 -16.09(11) . . . . ?
C17 C1 C2 C5 -162.86(8) . . . . ?
C3 C1 C2 C5 94.68(8) . . . . ?
C6 C1 C2 C3 -110.77(9) . . . . ?
C17 C1 C2 C3 102.46(8) . . . . ?
C5 C2 C3 C4 2.40(9) . . . . ?
C1 C2 C3 C4 112.26(8) . . . . ?
C5 C2 C3 C1 -109.86(8) . . . . ?
C6 C1 C3 C4 12.27(12) . . . . ?
C17 C1 C3 C4 157.54(8) . . . . ?
C2 C1 C3 C4 -94.28(9) . . . . ?
C6 C1 C3 C2 106.55(9) . . . . ?
C17 C1 C3 C2 -108.18(8) . . . . ?
C2 C3 C4 O4 175.81(9) . . . . ?
C1 C3 C4 O4 -119.60(10) . . . . ?
C2 C3 C4 N4 -4.02(9) . . . . ?
C1 C3 C4 N4 60.57(10) . . . . ?
O4 C4 N4 C5 -175.56(9) . . . . ?
C3 C4 N4 C5 4.27(10) . . . . ?
O4 C4 N4 C23 2.86(15) . . . . ?
C3 C4 N4 C23 -177.31(8) . . . . ?
C4 N4 C5 O5 177.22(9) . . . . ?
C23 N4 C5 O5 -1.23(15) . . . . ?
C4 N4 C5 C2 -2.72(10) . . . . ?
C23 N4 C5 C2 178.83(8) . . . . ?
C3 C2 C5 O5 -179.91(9) . . . . ?
C1 C2 C5 O5 115.38(11) . . . . ?
C3 C2 C5 N4 0.03(10) . . . . ?
C1 C2 C5 N4 -64.68(10) . . . . ?
C17 C1 C6 C7 -98.98(10) . . . . ?
C2 C1 C6 C7 114.05(10) . . . . ?
C3 C1 C6 C7 45.40(12) . . . . ?
C17 C1 C6 C11 79.76(10) . . . . ?
C2 C1 C6 C11 -67.21(11) . . . . ?
C3 C1 C6 C11 -135.86(9) . . . . ?
C11 C6 C7 C8 0.65(14) . . . . ?
C1 C6 C7 C8 179.39(8) . . . . ?
C6 C7 C8 C9 0.45(15) . . . . ?
C7 C8 C9 C10 -0.18(15) . . . . ?
C8 C9 C10 C11 -1.21(16) . . . . ?
C9 C10 C11 C6 2.28(14) . . . . ?
C9 C10 C11 C12 -177.93(9) . . . . ?
C7 C6 C11 C10 -1.98(13) . . . . ?
C1 C6 C11 C10 179.27(8) . . . . ?
C7 C6 C11 C12 178.23(8) . . . . ?
C1 C6 C11 C12 -0.52(13) . . . . ?
C10 C11 C12 N12 18.33(12) . . . . ?
C6 C11 C12 N12 -161.88(8) . . . . ?
C11 C12 N12 C16 70.90(10) . . . . ?
C11 C12 N12 C13 -168.43(8) . . . . ?
C12 N12 C13 C14 179.65(8) . . . . ?
C16 N12 C13 C14 -57.75(10) . . . . ?
N12 C13 C14 O14 58.01(12) . . . . ?
C13 C14 O14 C15 -57.65(12) . . . . ?
C14 O14 C15 C16 58.55(11) . . . . ?
C12 N12 C16 C15 179.62(7) . . . . ?
C13 N12 C16 C15 58.65(10) . . . . ?
O14 C15 C16 N12 -60.03(10) . . . . ?
C6 C1 C17 C18 -171.94(8) . . . . ?
C2 C1 C17 C18 -24.46(12) . . . . ?
C3 C1 C17 C18 41.08(11) . . . . ?
C6 C1 C17 C22 11.56(12) . . . . ?
C2 C1 C17 C22 159.04(8) . . . . ?
C3 C1 C17 C22 -135.42(9) . . . . ?
C22 C17 C18 C19 0.90(14) . . . . ?
C1 C17 C18 C19 -175.65(8) . . . . ?
C17 C18 C19 C20 -0.61(14) . . . . ?
C18 C19 C20 C21 0.10(14) . . . . ?
C19 C20 C21 C22 0.10(14) . . . . ?
C20 C21 C22 C17 0.21(14) . . . . ?
C18 C17 C22 C21 -0.70(14) . . . . ?
C1 C17 C22 C21 175.90(8) . . . . ?
C4 N4 C23 C28 -59.92(13) . . . . ?
C5 N4 C23 C28 118.35(10) . . . . ?
C4 N4 C23 C24 122.43(11) . . . . ?
C5 N4 C23 C24 -59.30(13) . . . . ?
C28 C23 C24 C25 -1.38(16) . . . . ?
N4 C23 C24 C25 176.22(10) . . . . ?
C23 C24 C25 C26 0.85(18) . . . . ?
C24 C25 C26 C27 0.13(18) . . . . ?
C25 C26 C27 C28 -0.61(17) . . . . ?
C24 C23 C28 C27 0.91(15) . . . . ?
N4 C23 C28 C27 -176.71(9) . . . . ?
C26 C27 C28 C23 0.10(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12B O5 0.987(14) 2.537(14) 3.3684(12) 141.8(11) . yes
C13 H13A O5 0.963(14) 2.414(14) 3.2131(12) 140.1(11) 3_666 yes

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF3023FMI
_database_code_depnum_ccdc_archive 'CCDC 2087134'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 N O5'
_chemical_formula_sum            'C24 H27 N O5'
_chemical_formula_weight         409.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2062(10)
_cell_length_b                   11.4773(11)
_cell_length_c                   16.2488(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.0553(18)
_cell_angle_gamma                90
_cell_volume                     2084.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9262
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.69

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8832
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18508
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4785
_reflns_number_gt                4254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.9167P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4785
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60697(11) 0.31193(11) 0.32798(8) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.65206(8) 0.19538(8) 0.33784(6) 0.0256(2) Uani 1 1 d . . . . .
C2 C 0.61932(10) 0.35136(11) 0.23854(8) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.5860(14) 0.4276(15) 0.2337(10) 0.025(4) Uiso 1 1 d . . . . .
O2 O 0.48495(8) 0.30859(8) 0.34618(6) 0.0256(2) Uani 1 1 d . . . . .
C3 C 0.75205(11) 0.35068(11) 0.22078(8) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.7816(13) 0.2736(14) 0.2316(9) 0.018(3) Uiso 1 1 d . . . . .
C4 C 0.82323(10) 0.43865(11) 0.27722(8) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.8109(14) 0.5147(14) 0.2533(9) 0.020(4) Uiso 1 1 d . . . . .
C5 C 0.78258(10) 0.44416(11) 0.36476(8) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.67683(11) 0.39260(11) 0.38759(8) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.63869(12) 0.41142(12) 0.46639(9) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.5647(16) 0.3786(16) 0.4798(11) 0.032(4) Uiso 1 1 d . . . . .
C8 C 0.70562(13) 0.47883(13) 0.52321(9) 0.0298(3) Uani 1 1 d . . . . .
H8 H 0.6753(16) 0.4876(16) 0.5789(12) 0.037(5) Uiso 1 1 d . . . . .
C9 C 0.81301(12) 0.52725(12) 0.50194(9) 0.0276(3) Uani 1 1 d . . . . .
H9 H 0.8586(16) 0.5748(16) 0.5426(11) 0.034(4) Uiso 1 1 d . . . . .
C10 C 0.85028(11) 0.51033(12) 0.42326(8) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.9224(15) 0.5456(15) 0.4080(10) 0.029(4) Uiso 1 1 d . . . . .
C11 C 0.56693(13) 0.13011(13) 0.38131(10) 0.0326(3) Uani 1 1 d . . . . .
H11A H 0.5824(16) 0.1407(17) 0.4428(12) 0.037(5) Uiso 1 1 d . . . . .
H11B H 0.5699(16) 0.0501(17) 0.3634(11) 0.035(4) Uiso 1 1 d . . . . .
C12 C 0.45042(13) 0.18865(13) 0.35347(10) 0.0314(3) Uani 1 1 d . . . . .
H12A H 0.4177(15) 0.1551(15) 0.3007(11) 0.027(4) Uiso 1 1 d . . . . .
H12B H 0.3905(17) 0.1837(16) 0.3912(12) 0.035(5) Uiso 1 1 d . . . . .
C13 C 0.54913(11) 0.27174(12) 0.17823(8) 0.0242(3) Uani 1 1 d . . . . .
O13 O 0.58571(10) 0.18092(9) 0.15380(7) 0.0364(3) Uani 1 1 d . . . . .
C14 C 0.36673(14) 0.24522(14) 0.09741(11) 0.0353(3) Uani 1 1 d . . . . .
H14A H 0.3343(19) 0.1828(19) 0.1280(13) 0.048(6) Uiso 1 1 d . . . . .
H14B H 0.4188(19) 0.2099(18) 0.0574(13) 0.047(5) Uiso 1 1 d . . . . .
O14 O 0.44125(8) 0.31610(8) 0.15511(6) 0.0277(2) Uani 1 1 d . . . . .
C15 C 0.27213(14) 0.32283(14) 0.05711(10) 0.0332(3) Uani 1 1 d . . . . .
H15A H 0.2195(19) 0.3577(19) 0.1008(13) 0.051(6) Uiso 1 1 d . . . . .
H15B H 0.2210(18) 0.2716(18) 0.0158(13) 0.049(5) Uiso 1 1 d . . . . .
H15C H 0.3113(19) 0.3854(19) 0.0260(13) 0.051(6) Uiso 1 1 d . . . . .
C16 C 0.76430(11) 0.38915(12) 0.13137(8) 0.0243(3) Uani 1 1 d . . . . .
N16 N 0.84310(10) 0.33440(10) 0.08590(7) 0.0249(3) Uani 1 1 d . . . . .
O16 O 0.70470(10) 0.47253(10) 0.10442(7) 0.0379(3) Uani 1 1 d . . . . .
C17 C 0.86305(15) 0.37849(16) 0.00367(9) 0.0349(3) Uani 1 1 d . . . . .
H17A H 0.8294(19) 0.3232(19) -0.0411(13) 0.049(6) Uiso 1 1 d . . . . .
H17B H 0.9516(16) 0.3830(16) -0.0006(11) 0.034(5) Uiso 1 1 d . . . . .
H17C H 0.833(2) 0.457(2) -0.0033(15) 0.066(7) Uiso 1 1 d . . . . .
C18 C 0.91276(14) 0.23173(14) 0.11042(10) 0.0329(3) Uani 1 1 d . . . . .
H18A H 0.992(2) 0.253(2) 0.1367(14) 0.062(7) Uiso 1 1 d . . . . .
H18B H 0.9263(18) 0.1869(17) 0.0596(13) 0.043(5) Uiso 1 1 d . . . . .
H18C H 0.8699(19) 0.1837(18) 0.1455(13) 0.045(5) Uiso 1 1 d . . . . .
C19 C 0.95719(11) 0.41657(11) 0.27698(8) 0.0221(3) Uani 1 1 d . . . . .
C20 C 1.03091(12) 0.49464(13) 0.23956(9) 0.0282(3) Uani 1 1 d . . . . .
H20 H 0.9974(15) 0.5644(15) 0.2140(10) 0.026(4) Uiso 1 1 d . . . . .
C21 C 1.15436(13) 0.47492(14) 0.24025(10) 0.0343(3) Uani 1 1 d . . . . .
H21 H 1.2018(18) 0.5313(18) 0.2148(12) 0.043(5) Uiso 1 1 d . . . . .
C22 C 1.20362(12) 0.37610(15) 0.27677(10) 0.0331(3) Uani 1 1 d . . . . .
H22 H 1.2886(19) 0.3631(18) 0.2776(12) 0.045(5) Uiso 1 1 d . . . . .
C23 C 1.13051(12) 0.29625(14) 0.31368(9) 0.0300(3) Uani 1 1 d . . . . .
H23 H 1.1649(17) 0.2254(17) 0.3413(12) 0.038(5) Uiso 1 1 d . . . . .
C24 C 1.00786(11) 0.31707(12) 0.31412(8) 0.0251(3) Uani 1 1 d . . . . .
H24 H 0.9542(15) 0.2610(15) 0.3421(10) 0.028(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.4199(14) . ?
C1 O1 1.4349(15) . ?
C1 C6 1.5170(17) . ?
C1 C2 1.5377(18) . ?
O1 C11 1.4372(17) . ?
C2 C13 1.5182(17) . ?
C2 C3 1.5350(16) . ?
C2 H2 0.952(17) . ?
O2 C12 1.4371(17) . ?
C3 C16 1.5339(18) . ?
C3 C4 1.5471(17) . ?
C3 H3 0.956(16) . ?
C4 C19 1.5227(16) . ?
C4 C5 1.5252(17) . ?
C4 H4 0.962(16) . ?
C5 C10 1.3979(18) . ?
C5 C6 1.3979(17) . ?
C6 C7 1.3951(19) . ?
C7 C8 1.384(2) . ?
C7 H7 0.950(18) . ?
C8 C9 1.391(2) . ?
C8 H8 0.994(19) . ?
C9 C10 1.386(2) . ?
C9 H9 0.974(19) . ?
C10 H10 0.952(17) . ?
C11 C12 1.509(2) . ?
C11 H11A 1.010(19) . ?
C11 H11B 0.965(19) . ?
C12 H12A 0.986(17) . ?
C12 H12B 0.943(19) . ?
C13 O13 1.1980(17) . ?
C13 O14 1.3408(15) . ?
C14 O14 1.4586(17) . ?
C14 C15 1.499(2) . ?
C14 H14A 0.96(2) . ?
C14 H14B 0.99(2) . ?
C15 H15A 1.04(2) . ?
C15 H15B 1.03(2) . ?
C15 H15C 1.00(2) . ?
C16 O16 1.2298(17) . ?
C16 N16 1.3464(17) . ?
N16 C18 1.4535(18) . ?
N16 C17 1.4607(18) . ?
C17 H17A 1.02(2) . ?
C17 H17B 1.001(18) . ?
C17 H17C 0.96(3) . ?
C18 H18A 0.99(2) . ?
C18 H18B 0.99(2) . ?
C18 H18C 0.95(2) . ?
C19 C20 1.3878(19) . ?
C19 C24 1.3937(19) . ?
C20 C21 1.4011(19) . ?
C20 H20 0.966(17) . ?
C21 C22 1.377(2) . ?
C21 H21 0.95(2) . ?
C22 C23 1.393(2) . ?
C22 H22 0.96(2) . ?
C23 C24 1.3955(18) . ?
C23 H23 0.99(2) . ?
C24 H24 1.010(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 106.76(9) . . ?
O2 C1 C6 110.16(10) . . ?
O1 C1 C6 109.63(10) . . ?
O2 C1 C2 110.92(10) . . ?
O1 C1 C2 108.99(10) . . ?
C6 C1 C2 110.31(10) . . ?
C1 O1 C11 107.46(10) . . ?
C13 C2 C3 109.89(10) . . ?
C13 C2 C1 110.84(10) . . ?
C3 C2 C1 109.23(10) . . ?
C13 C2 H2 108.5(10) . . ?
C3 C2 H2 111.6(10) . . ?
C1 C2 H2 106.7(10) . . ?
C1 O2 C12 108.17(10) . . ?
C16 C3 C2 109.23(10) . . ?
C16 C3 C4 107.25(10) . . ?
C2 C3 C4 110.56(10) . . ?
C16 C3 H3 112.8(9) . . ?
C2 C3 H3 107.3(9) . . ?
C4 C3 H3 109.7(9) . . ?
C19 C4 C5 111.65(10) . . ?
C19 C4 C3 110.91(10) . . ?
C5 C4 C3 113.85(10) . . ?
C19 C4 H4 105.3(9) . . ?
C5 C4 H4 107.2(9) . . ?
C3 C4 H4 107.4(9) . . ?
C10 C5 C6 118.62(12) . . ?
C10 C5 C4 118.24(11) . . ?
C6 C5 C4 123.00(11) . . ?
C7 C6 C5 119.91(12) . . ?
C7 C6 C1 120.18(11) . . ?
C5 C6 C1 119.85(11) . . ?
C8 C7 C6 120.79(12) . . ?
C8 C7 H7 120.7(11) . . ?
C6 C7 H7 118.5(11) . . ?
C7 C8 C9 119.68(13) . . ?
C7 C8 H8 117.4(11) . . ?
C9 C8 H8 122.9(11) . . ?
C10 C9 C8 119.70(13) . . ?
C10 C9 H9 121.8(10) . . ?
C8 C9 H9 118.5(10) . . ?
C9 C10 C5 121.25(12) . . ?
C9 C10 H10 119.8(10) . . ?
C5 C10 H10 119.0(10) . . ?
O1 C11 C12 102.18(11) . . ?
O1 C11 H11A 110.5(11) . . ?
C12 C11 H11A 109.1(11) . . ?
O1 C11 H11B 108.0(11) . . ?
C12 C11 H11B 112.4(11) . . ?
H11A C11 H11B 114.0(15) . . ?
O2 C12 C11 102.64(11) . . ?
O2 C12 H12A 112.8(10) . . ?
C11 C12 H12A 110.3(10) . . ?
O2 C12 H12B 108.6(11) . . ?
C11 C12 H12B 114.8(11) . . ?
H12A C12 H12B 107.7(15) . . ?
O13 C13 O14 124.09(12) . . ?
O13 C13 C2 124.32(12) . . ?
O14 C13 C2 111.59(11) . . ?
O14 C14 C15 107.72(12) . . ?
O14 C14 H14A 107.7(13) . . ?
C15 C14 H14A 112.8(13) . . ?
O14 C14 H14B 108.3(12) . . ?
C15 C14 H14B 112.8(12) . . ?
H14A C14 H14B 107.3(18) . . ?
C13 O14 C14 115.61(11) . . ?
C14 C15 H15A 110.5(12) . . ?
C14 C15 H15B 106.7(12) . . ?
H15A C15 H15B 110.4(16) . . ?
C14 C15 H15C 109.1(12) . . ?
H15A C15 H15C 111.2(17) . . ?
H15B C15 H15C 108.9(17) . . ?
O16 C16 N16 121.91(12) . . ?
O16 C16 C3 118.59(11) . . ?
N16 C16 C3 119.44(11) . . ?
C16 N16 C18 126.04(12) . . ?
C16 N16 C17 119.28(12) . . ?
C18 N16 C17 114.68(11) . . ?
N16 C17 H17A 111.4(12) . . ?
N16 C17 H17B 107.4(10) . . ?
H17A C17 H17B 107.6(16) . . ?
N16 C17 H17C 110.9(15) . . ?
H17A C17 H17C 113.1(19) . . ?
H17B C17 H17C 106.2(18) . . ?
N16 C18 H18A 111.5(14) . . ?
N16 C18 H18B 107.6(11) . . ?
H18A C18 H18B 107.5(17) . . ?
N16 C18 H18C 110.6(12) . . ?
H18A C18 H18C 111.3(19) . . ?
H18B C18 H18C 108.2(17) . . ?
C20 C19 C24 118.81(12) . . ?
C20 C19 C4 120.74(12) . . ?
C24 C19 C4 120.45(11) . . ?
C19 C20 C21 120.67(14) . . ?
C19 C20 H20 119.9(10) . . ?
C21 C20 H20 119.4(10) . . ?
C22 C21 C20 120.13(14) . . ?
C22 C21 H21 121.9(12) . . ?
C20 C21 H21 118.0(12) . . ?
C21 C22 C23 119.82(13) . . ?
C21 C22 H22 119.9(12) . . ?
C23 C22 H22 120.2(12) . . ?
C22 C23 C24 119.93(14) . . ?
C22 C23 H23 120.8(11) . . ?
C24 C23 H23 119.3(11) . . ?
C19 C24 C23 120.62(13) . . ?
C19 C24 H24 118.6(9) . . ?
C23 C24 H24 120.7(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 C11 -14.21(14) . . . . ?
C6 C1 O1 C11 105.10(12) . . . . ?
C2 C1 O1 C11 -134.08(11) . . . . ?
O2 C1 C2 C13 -57.31(13) . . . . ?
O1 C1 C2 C13 59.95(12) . . . . ?
C6 C1 C2 C13 -179.64(10) . . . . ?
O2 C1 C2 C3 -178.53(10) . . . . ?
O1 C1 C2 C3 -61.27(12) . . . . ?
C6 C1 C2 C3 59.13(13) . . . . ?
O1 C1 O2 C12 -9.46(14) . . . . ?
C6 C1 O2 C12 -128.43(11) . . . . ?
C2 C1 O2 C12 109.15(12) . . . . ?
C13 C2 C3 C16 57.79(13) . . . . ?
C1 C2 C3 C16 179.59(10) . . . . ?
C13 C2 C3 C4 175.59(10) . . . . ?
C1 C2 C3 C4 -62.61(13) . . . . ?
C16 C3 C4 C19 -76.07(12) . . . . ?
C2 C3 C4 C19 164.93(10) . . . . ?
C16 C3 C4 C5 157.01(10) . . . . ?
C2 C3 C4 C5 38.01(14) . . . . ?
C19 C4 C5 C10 45.88(15) . . . . ?
C3 C4 C5 C10 172.41(11) . . . . ?
C19 C4 C5 C6 -138.49(12) . . . . ?
C3 C4 C5 C6 -11.95(16) . . . . ?
C10 C5 C6 C7 2.40(18) . . . . ?
C4 C5 C6 C7 -173.21(12) . . . . ?
C10 C5 C6 C1 -174.78(11) . . . . ?
C4 C5 C6 C1 9.60(18) . . . . ?
O2 C1 C6 C7 27.11(16) . . . . ?
O1 C1 C6 C7 -90.09(14) . . . . ?
C2 C1 C6 C7 149.89(12) . . . . ?
O2 C1 C6 C5 -155.71(11) . . . . ?
O1 C1 C6 C5 87.09(14) . . . . ?
C2 C1 C6 C5 -32.93(15) . . . . ?
C5 C6 C7 C8 -1.3(2) . . . . ?
C1 C6 C7 C8 175.85(13) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C10 1.9(2) . . . . ?
C8 C9 C10 C5 -0.7(2) . . . . ?
C6 C5 C10 C9 -1.39(19) . . . . ?
C4 C5 C10 C9 174.44(12) . . . . ?
C1 O1 C11 C12 30.65(14) . . . . ?
C1 O2 C12 C11 27.88(15) . . . . ?
O1 C11 C12 O2 -35.35(15) . . . . ?
C3 C2 C13 O13 37.35(18) . . . . ?
C1 C2 C13 O13 -83.48(16) . . . . ?
C3 C2 C13 O14 -142.17(11) . . . . ?
C1 C2 C13 O14 97.00(12) . . . . ?
O13 C13 O14 C14 0.8(2) . . . . ?
C2 C13 O14 C14 -179.65(12) . . . . ?
C15 C14 O14 C13 -160.98(13) . . . . ?
C2 C3 C16 O16 43.26(16) . . . . ?
C4 C3 C16 O16 -76.59(15) . . . . ?
C2 C3 C16 N16 -139.52(12) . . . . ?
C4 C3 C16 N16 100.63(13) . . . . ?
O16 C16 N16 C18 -176.50(14) . . . . ?
C3 C16 N16 C18 6.4(2) . . . . ?
O16 C16 N16 C17 3.1(2) . . . . ?
C3 C16 N16 C17 -174.04(12) . . . . ?
C5 C4 C19 C20 -121.68(13) . . . . ?
C3 C4 C19 C20 110.19(14) . . . . ?
C5 C4 C19 C24 58.60(15) . . . . ?
C3 C4 C19 C24 -69.52(15) . . . . ?
C24 C19 C20 C21 -1.1(2) . . . . ?
C4 C19 C20 C21 179.22(13) . . . . ?
C19 C20 C21 C22 1.4(2) . . . . ?
C20 C21 C22 C23 -0.6(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C4 C19 C24 C23 179.69(12) . . . . ?
C22 C23 C24 C19 0.8(2) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2954FMI_MO_190K
_database_code_depnum_ccdc_archive 'CCDC 2087132'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UCDAVIS
United States of America
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H28 N2 O10'
_chemical_formula_sum            'C34 H28 N2 O10'
_chemical_formula_weight         624.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3403(4)
_cell_length_b                   11.8742(4)
_cell_length_c                   12.8266(5)
_cell_angle_alpha                75.4010(15)
_cell_angle_beta                 71.3610(15)
_cell_angle_gamma                62.6841(13)
_cell_volume                     1442.67(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.01

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  1.0102
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11871
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             6538
_reflns_number_gt                5790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.7219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0112(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6538
_refine_ls_number_parameters     528
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29872(12) 0.42198(11) 0.09220(9) 0.0137(2) Uani 1 1 d . . . . .
H1 H 0.3874(16) 0.4295(15) 0.0561(13) 0.018(4) Uiso 1 1 d . . . . .
C2 C 0.19528(12) 0.54659(11) 0.14292(9) 0.0137(2) Uani 1 1 d . . . . .
H2 H 0.1045(15) 0.5471(14) 0.1689(12) 0.014(3) Uiso 1 1 d . . . . .
C3 C 0.18518(12) 0.65859(11) 0.05004(9) 0.0145(2) Uani 1 1 d . . . . .
O3 O 0.31764(8) 0.66040(8) 0.00992(7) 0.01615(18) Uani 1 1 d . . . . .
C4 C 0.13615(12) 0.64486(11) -0.04187(9) 0.0154(2) Uani 1 1 d . . . . .
O4 O 0.09471(9) 0.77740(8) 0.09214(7) 0.01685(18) Uani 1 1 d . . . . .
C5 C 0.05943(13) 0.75390(12) -0.10498(10) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.0378(17) 0.8375(16) -0.0893(14) 0.024(4) Uiso 1 1 d . . . . .
C6 C 0.01686(13) 0.74224(13) -0.19024(11) 0.0223(3) Uani 1 1 d . . . . .
H6 H -0.0347(18) 0.8190(18) -0.2344(15) 0.033(5) Uiso 1 1 d . . . . .
C7 C 0.04848(13) 0.62115(13) -0.21237(10) 0.0208(3) Uani 1 1 d . . . . .
H7 H 0.0218(17) 0.6122(16) -0.2743(14) 0.024(4) Uiso 1 1 d . . . . .
C8 C 0.12211(13) 0.51308(13) -0.14894(10) 0.0180(2) Uani 1 1 d . . . . .
H8 H 0.1426(16) 0.4297(15) -0.1638(13) 0.018(4) Uiso 1 1 d . . . . .
C9 C 0.16770(12) 0.52328(12) -0.06338(9) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.24611(12) 0.40045(11) 0.00393(9) 0.0137(2) Uani 1 1 d . . . . .
H10 H 0.1812(15) 0.3612(14) 0.0431(12) 0.013(3) Uiso 1 1 d . . . . .
C11 C 0.32915(12) 0.30216(11) 0.17643(10) 0.0153(2) Uani 1 1 d . . . . .
H11A H 0.2462(15) 0.3012(14) 0.2332(12) 0.015(3) Uiso 1 1 d . . . . .
H11B H 0.3701(17) 0.2257(16) 0.1401(14) 0.023(4) Uiso 1 1 d . . . . .
O11 O 0.42702(9) 0.29482(8) 0.23180(7) 0.01588(18) Uani 1 1 d . . . . .
C12 C 0.46470(12) 0.19184(11) 0.30759(9) 0.0158(2) Uani 1 1 d . . . . .
O12 O 0.42178(11) 0.11042(9) 0.32968(8) 0.0253(2) Uani 1 1 d . . . . .
C13 C 0.56534(12) 0.19030(12) 0.36102(9) 0.0156(2) Uani 1 1 d . . . . .
C14 C 0.60489(13) 0.29099(13) 0.33855(11) 0.0208(3) Uani 1 1 d . . . . .
H14 H 0.5642(19) 0.3643(18) 0.2889(15) 0.033(5) Uiso 1 1 d . . . . .
C15 C 0.70007(14) 0.28455(14) 0.38889(11) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.7275(17) 0.3542(17) 0.3741(14) 0.027(4) Uiso 1 1 d . . . . .
C16 C 0.75380(13) 0.17607(13) 0.46078(10) 0.0207(3) Uani 1 1 d . . . . .
N16 N 0.86064(12) 0.16557(13) 0.50958(9) 0.0263(3) Uani 1 1 d . . . . .
O16 O 0.88430(11) 0.08812(12) 0.59240(9) 0.0361(3) Uani 1 1 d . . . . .
C17 C 0.71473(13) 0.07598(13) 0.48663(10) 0.0207(3) Uani 1 1 d . . . . .
H17 H 0.7558(17) 0.0020(17) 0.5346(14) 0.027(4) Uiso 1 1 d . . . . .
O17 O 0.92250(12) 0.23333(13) 0.46355(9) 0.0377(3) Uani 1 1 d . . . . .
C18 C 0.61965(13) 0.08371(12) 0.43555(10) 0.0188(3) Uani 1 1 d . . . . .
H18 H 0.5908(16) 0.0147(15) 0.4511(13) 0.018(4) Uiso 1 1 d . . . . .
C19 C 0.23168(13) 0.56968(12) 0.23781(9) 0.0155(2) Uani 1 1 d . . . . .
H19A H 0.3298(15) 0.5455(14) 0.2241(12) 0.012(3) Uiso 1 1 d . . . . .
H19B H 0.1824(16) 0.6583(15) 0.2518(12) 0.017(4) Uiso 1 1 d . . . . .
O19 O 0.19245(9) 0.49032(8) 0.33660(7) 0.01624(18) Uani 1 1 d . . . . .
C20 C 0.24278(13) 0.47915(12) 0.42208(10) 0.0169(2) Uani 1 1 d . . . . .
O20 O 0.30567(12) 0.53771(10) 0.42309(8) 0.0278(2) Uani 1 1 d . . . . .
C21 C 0.21574(13) 0.38183(11) 0.51466(9) 0.0161(2) Uani 1 1 d . . . . .
C22 C 0.12834(13) 0.32778(12) 0.51740(10) 0.0177(2) Uani 1 1 d . . . . .
H22 H 0.0802(17) 0.3560(16) 0.4612(14) 0.026(4) Uiso 1 1 d . . . . .
C23 C 0.11129(13) 0.23367(12) 0.60258(10) 0.0183(2) Uani 1 1 d . . . . .
H23 H 0.0541(17) 0.1948(16) 0.6043(14) 0.025(4) Uiso 1 1 d . . . . .
C24 C 0.18382(13) 0.19575(12) 0.68335(10) 0.0176(2) Uani 1 1 d . . . . .
N24 N 0.17148(11) 0.09167(10) 0.77166(9) 0.0204(2) Uani 1 1 d . . . . .
O24 O 0.11059(10) 0.03332(9) 0.76256(8) 0.0249(2) Uani 1 1 d . . . . .
C25 C 0.27101(14) 0.24782(13) 0.68343(10) 0.0211(3) Uani 1 1 d . . . . .
H25 H 0.3196(19) 0.2160(17) 0.7402(15) 0.034(5) Uiso 1 1 d . . . . .
O25 O 0.22463(11) 0.06854(11) 0.84867(9) 0.0326(3) Uani 1 1 d . . . . .
C26 C 0.28668(14) 0.34225(13) 0.59783(10) 0.0208(3) Uani 1 1 d . . . . .
H26 H 0.3506(18) 0.3791(17) 0.5941(14) 0.030(4) Uiso 1 1 d . . . . .
C27 C 0.29369(13) 0.79255(12) -0.02277(11) 0.0194(3) Uani 1 1 d . . . . .
H27A H 0.2782(16) 0.8191(15) -0.0987(13) 0.019(4) Uiso 1 1 d . . . . .
H27B H 0.3731(17) 0.8012(16) -0.0214(13) 0.024(4) Uiso 1 1 d . . . . .
C28 C 0.16611(13) 0.85916(12) 0.06341(11) 0.0202(3) Uani 1 1 d . . . . .
H28A H 0.1876(17) 0.8627(16) 0.1324(14) 0.025(4) Uiso 1 1 d . . . . .
H28B H 0.1072(18) 0.9457(17) 0.0349(14) 0.029(4) Uiso 1 1 d . . . . .
C29 C 0.36289(12) 0.30511(11) -0.07168(9) 0.0145(2) Uani 1 1 d . . . . .
C30 C 0.37891(13) 0.17944(12) -0.05915(10) 0.0172(2) Uani 1 1 d . . . . .
H30 H 0.3131(16) 0.1507(15) -0.0038(13) 0.021(4) Uiso 1 1 d . . . . .
C31 C 0.48736(14) 0.09244(12) -0.12807(11) 0.0210(3) Uani 1 1 d . . . . .
H31 H 0.4950(17) 0.0038(17) -0.1194(14) 0.027(4) Uiso 1 1 d . . . . .
C32 C 0.57977(14) 0.13074(13) -0.21040(11) 0.0218(3) Uani 1 1 d . . . . .
H32 H 0.6532(17) 0.0708(16) -0.2606(14) 0.024(4) Uiso 1 1 d . . . . .
C33 C 0.56398(14) 0.25675(13) -0.22485(11) 0.0219(3) Uani 1 1 d . . . . .
H33 H 0.6267(19) 0.2861(17) -0.2813(15) 0.033(5) Uiso 1 1 d . . . . .
C34 C 0.45688(13) 0.34300(12) -0.15544(10) 0.0185(2) Uani 1 1 d . . . . .
H34 H 0.4442(16) 0.4330(16) -0.1650(13) 0.021(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.5243(16) . ?
C1 C2 1.5470(16) . ?
C1 C10 1.5558(16) . ?
C1 H1 0.999(16) . ?
C2 C19 1.5232(16) . ?
C2 C3 1.5329(15) . ?
C2 H2 0.973(15) . ?
C3 O4 1.4269(14) . ?
C3 O3 1.4324(14) . ?
C3 C4 1.5247(16) . ?
O3 C27 1.4359(14) . ?
C4 C9 1.3971(17) . ?
C4 C5 1.4059(17) . ?
O4 C28 1.4437(15) . ?
C5 C6 1.3869(19) . ?
C5 H5 0.965(17) . ?
C6 C7 1.394(2) . ?
C6 H6 0.977(19) . ?
C7 C8 1.3894(18) . ?
C7 H7 0.980(17) . ?
C8 C9 1.4048(17) . ?
C8 H8 0.963(16) . ?
C9 C10 1.5261(16) . ?
C10 C29 1.5272(16) . ?
C10 H10 0.986(15) . ?
C11 O11 1.4587(14) . ?
C11 H11A 0.991(15) . ?
C11 H11B 0.972(17) . ?
O11 C12 1.3452(14) . ?
C12 O12 1.2073(16) . ?
C12 C13 1.4990(17) . ?
C13 C18 1.3950(17) . ?
C13 C14 1.3962(18) . ?
C14 C15 1.3902(19) . ?
C14 H14 0.957(19) . ?
C15 C16 1.3859(19) . ?
C15 H15 0.968(17) . ?
C16 C17 1.3818(19) . ?
C16 N16 1.4772(16) . ?
N16 O17 1.2255(16) . ?
N16 O16 1.2286(16) . ?
C17 C18 1.3895(18) . ?
C17 H17 0.950(18) . ?
C18 H18 0.969(16) . ?
C19 O19 1.4540(13) . ?
C19 H19A 0.979(15) . ?
C19 H19B 0.971(16) . ?
O19 C20 1.3427(15) . ?
C20 O20 1.2075(16) . ?
C20 C21 1.4967(16) . ?
C21 C22 1.3948(18) . ?
C21 C26 1.3982(17) . ?
C22 C23 1.3884(17) . ?
C22 H22 0.944(18) . ?
C23 C24 1.3863(18) . ?
C23 H23 0.946(17) . ?
C24 C25 1.3863(18) . ?
C24 N24 1.4771(15) . ?
N24 O24 1.2254(15) . ?
N24 O25 1.2274(15) . ?
C25 C26 1.3900(17) . ?
C25 H25 0.950(19) . ?
C26 H26 0.989(18) . ?
C27 C28 1.5195(17) . ?
C27 H27A 0.992(16) . ?
C27 H27B 0.958(17) . ?
C28 H28A 1.005(17) . ?
C28 H28B 0.987(18) . ?
C29 C30 1.3909(17) . ?
C29 C34 1.3991(17) . ?
C30 C31 1.4002(18) . ?
C30 H30 0.975(16) . ?
C31 C32 1.3813(19) . ?
C31 H31 0.995(17) . ?
C32 C33 1.3931(19) . ?
C32 H32 0.979(17) . ?
C33 C34 1.3941(18) . ?
C33 H33 0.961(19) . ?
C34 H34 0.992(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 114.31(9) . . ?
C11 C1 C10 107.44(9) . . ?
C2 C1 C10 110.59(9) . . ?
C11 C1 H1 106.6(9) . . ?
C2 C1 H1 108.4(9) . . ?
C10 C1 H1 109.3(9) . . ?
C19 C2 C3 109.28(9) . . ?
C19 C2 C1 114.43(10) . . ?
C3 C2 C1 107.93(9) . . ?
C19 C2 H2 108.8(9) . . ?
C3 C2 H2 106.0(9) . . ?
C1 C2 H2 110.1(9) . . ?
O4 C3 O3 106.44(9) . . ?
O4 C3 C4 109.61(9) . . ?
O3 C3 C4 111.76(9) . . ?
O4 C3 C2 110.85(9) . . ?
O3 C3 C2 107.31(9) . . ?
C4 C3 C2 110.78(10) . . ?
C3 O3 C27 105.74(9) . . ?
C9 C4 C5 119.91(11) . . ?
C9 C4 C3 119.77(10) . . ?
C5 C4 C3 120.31(11) . . ?
C3 O4 C28 108.94(9) . . ?
C6 C5 C4 120.68(12) . . ?
C6 C5 H5 120.0(10) . . ?
C4 C5 H5 119.3(10) . . ?
C5 C6 C7 119.66(12) . . ?
C5 C6 H6 119.7(11) . . ?
C7 C6 H6 120.6(11) . . ?
C8 C7 C6 119.91(12) . . ?
C8 C7 H7 120.0(10) . . ?
C6 C7 H7 120.0(10) . . ?
C7 C8 C9 121.10(12) . . ?
C7 C8 H8 119.6(9) . . ?
C9 C8 H8 119.3(9) . . ?
C4 C9 C8 118.72(11) . . ?
C4 C9 C10 123.11(10) . . ?
C8 C9 C10 118.15(11) . . ?
C9 C10 C29 111.21(9) . . ?
C9 C10 C1 114.00(10) . . ?
C29 C10 C1 110.79(9) . . ?
C9 C10 H10 106.0(8) . . ?
C29 C10 H10 106.4(8) . . ?
C1 C10 H10 108.0(8) . . ?
O11 C11 C1 108.87(9) . . ?
O11 C11 H11A 108.8(9) . . ?
C1 C11 H11A 112.7(9) . . ?
O11 C11 H11B 107.7(10) . . ?
C1 C11 H11B 111.0(10) . . ?
H11A C11 H11B 107.7(13) . . ?
C12 O11 C11 115.12(9) . . ?
O12 C12 O11 123.50(11) . . ?
O12 C12 C13 124.21(11) . . ?
O11 C12 C13 112.29(10) . . ?
C18 C13 C14 120.04(12) . . ?
C18 C13 C12 117.75(11) . . ?
C14 C13 C12 122.21(11) . . ?
C15 C14 C13 120.20(12) . . ?
C15 C14 H14 121.2(11) . . ?
C13 C14 H14 118.6(11) . . ?
C16 C15 C14 118.13(13) . . ?
C16 C15 H15 121.2(10) . . ?
C14 C15 H15 120.7(10) . . ?
C17 C16 C15 123.12(12) . . ?
C17 C16 N16 118.52(12) . . ?
C15 C16 N16 118.34(12) . . ?
O17 N16 O16 123.73(12) . . ?
O17 N16 C16 117.81(11) . . ?
O16 N16 C16 118.45(12) . . ?
C16 C17 C18 118.07(12) . . ?
C16 C17 H17 120.8(10) . . ?
C18 C17 H17 121.1(10) . . ?
C17 C18 C13 120.42(12) . . ?
C17 C18 H18 120.2(9) . . ?
C13 C18 H18 119.4(9) . . ?
O19 C19 C2 107.30(9) . . ?
O19 C19 H19A 108.1(8) . . ?
C2 C19 H19A 112.1(8) . . ?
O19 C19 H19B 108.5(9) . . ?
C2 C19 H19B 111.7(9) . . ?
H19A C19 H19B 109.0(12) . . ?
C20 O19 C19 114.62(9) . . ?
O20 C20 O19 124.22(11) . . ?
O20 C20 C21 123.94(11) . . ?
O19 C20 C21 111.80(10) . . ?
C22 C21 C26 120.40(11) . . ?
C22 C21 C20 122.48(11) . . ?
C26 C21 C20 117.06(11) . . ?
C23 C22 C21 120.32(12) . . ?
C23 C22 H22 120.1(10) . . ?
C21 C22 H22 119.6(10) . . ?
C24 C23 C22 117.93(12) . . ?
C24 C23 H23 121.0(10) . . ?
C22 C23 H23 121.1(10) . . ?
C25 C24 C23 123.26(11) . . ?
C25 C24 N24 118.20(11) . . ?
C23 C24 N24 118.51(11) . . ?
O24 N24 O25 124.45(11) . . ?
O24 N24 C24 118.03(11) . . ?
O25 N24 C24 117.51(11) . . ?
C24 C25 C26 118.16(12) . . ?
C24 C25 H25 119.1(11) . . ?
C26 C25 H25 122.7(11) . . ?
C25 C26 C21 119.94(12) . . ?
C25 C26 H26 120.1(10) . . ?
C21 C26 H26 119.9(10) . . ?
O3 C27 C28 102.76(9) . . ?
O3 C27 H27A 109.5(9) . . ?
C28 C27 H27A 112.0(9) . . ?
O3 C27 H27B 107.8(10) . . ?
C28 C27 H27B 114.4(10) . . ?
H27A C27 H27B 110.1(13) . . ?
O4 C28 C27 103.40(10) . . ?
O4 C28 H28A 108.0(9) . . ?
C27 C28 H28A 112.5(10) . . ?
O4 C28 H28B 109.5(10) . . ?
C27 C28 H28B 113.5(10) . . ?
H28A C28 H28B 109.7(14) . . ?
C30 C29 C34 118.49(11) . . ?
C30 C29 C10 121.30(10) . . ?
C34 C29 C10 120.22(11) . . ?
C29 C30 C31 120.79(12) . . ?
C29 C30 H30 120.7(9) . . ?
C31 C30 H30 118.5(9) . . ?
C32 C31 C30 120.27(12) . . ?
C32 C31 H31 120.2(10) . . ?
C30 C31 H31 119.4(10) . . ?
C31 C32 C33 119.56(12) . . ?
C31 C32 H32 120.2(10) . . ?
C33 C32 H32 120.2(10) . . ?
C32 C33 C34 120.16(12) . . ?
C32 C33 H33 121.4(11) . . ?
C34 C33 H33 118.4(11) . . ?
C33 C34 C29 120.71(12) . . ?
C33 C34 H34 121.0(9) . . ?
C29 C34 H34 118.3(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C19 53.30(13) . . . . ?
C10 C1 C2 C19 174.69(9) . . . . ?
C11 C1 C2 C3 175.18(9) . . . . ?
C10 C1 C2 C3 -63.42(12) . . . . ?
C19 C2 C3 O4 -52.91(12) . . . . ?
C1 C2 C3 O4 -177.91(9) . . . . ?
C19 C2 C3 O3 62.94(11) . . . . ?
C1 C2 C3 O3 -62.07(12) . . . . ?
C19 C2 C3 C4 -174.81(9) . . . . ?
C1 C2 C3 C4 60.18(12) . . . . ?
O4 C3 O3 C27 -28.40(11) . . . . ?
C4 C3 O3 C27 91.24(11) . . . . ?
C2 C3 O3 C27 -147.12(10) . . . . ?
O4 C3 C4 C9 -152.94(10) . . . . ?
O3 C3 C4 C9 89.30(12) . . . . ?
C2 C3 C4 C9 -30.31(14) . . . . ?
O4 C3 C4 C5 27.06(14) . . . . ?
O3 C3 C4 C5 -90.70(13) . . . . ?
C2 C3 C4 C5 149.70(11) . . . . ?
O3 C3 O4 C28 8.37(12) . . . . ?
C4 C3 O4 C28 -112.66(10) . . . . ?
C2 C3 O4 C28 124.75(10) . . . . ?
C9 C4 C5 C6 -1.34(18) . . . . ?
C3 C4 C5 C6 178.65(11) . . . . ?
C4 C5 C6 C7 1.10(19) . . . . ?
C5 C6 C7 C8 0.10(19) . . . . ?
C6 C7 C8 C9 -1.06(19) . . . . ?
C5 C4 C9 C8 0.39(17) . . . . ?
C3 C4 C9 C8 -179.61(10) . . . . ?
C5 C4 C9 C10 -177.80(11) . . . . ?
C3 C4 C9 C10 2.21(17) . . . . ?
C7 C8 C9 C4 0.81(17) . . . . ?
C7 C8 C9 C10 179.08(11) . . . . ?
C4 C9 C10 C29 -131.08(11) . . . . ?
C8 C9 C10 C29 50.73(14) . . . . ?
C4 C9 C10 C1 -4.96(15) . . . . ?
C8 C9 C10 C1 176.85(10) . . . . ?
C11 C1 C10 C9 160.84(10) . . . . ?
C2 C1 C10 C9 35.47(13) . . . . ?
C11 C1 C10 C29 -72.82(11) . . . . ?
C2 C1 C10 C29 161.81(9) . . . . ?
C2 C1 C11 O11 -79.72(12) . . . . ?
C10 C1 C11 O11 157.17(9) . . . . ?
C1 C11 O11 C12 -179.02(9) . . . . ?
C11 O11 C12 O12 -0.16(17) . . . . ?
C11 O11 C12 C13 179.92(9) . . . . ?
O12 C12 C13 C18 4.49(18) . . . . ?
O11 C12 C13 C18 -175.59(10) . . . . ?
O12 C12 C13 C14 -175.39(12) . . . . ?
O11 C12 C13 C14 4.53(16) . . . . ?
C18 C13 C14 C15 1.05(19) . . . . ?
C12 C13 C14 C15 -179.07(12) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 -1.6(2) . . . . ?
C14 C15 C16 N16 176.62(12) . . . . ?
C17 C16 N16 O17 159.12(13) . . . . ?
C15 C16 N16 O17 -19.22(19) . . . . ?
C17 C16 N16 O16 -19.53(18) . . . . ?
C15 C16 N16 O16 162.14(13) . . . . ?
C15 C16 C17 C18 1.73(19) . . . . ?
N16 C16 C17 C18 -176.52(11) . . . . ?
C16 C17 C18 C13 -0.39(18) . . . . ?
C14 C13 C18 C17 -0.96(18) . . . . ?
C12 C13 C18 C17 179.16(11) . . . . ?
C3 C2 C19 O19 159.73(9) . . . . ?
C1 C2 C19 O19 -79.13(12) . . . . ?
C2 C19 O19 C20 166.88(10) . . . . ?
C19 O19 C20 O20 6.30(17) . . . . ?
C19 O19 C20 C21 -171.71(10) . . . . ?
O20 C20 C21 C22 171.60(13) . . . . ?
O19 C20 C21 C22 -10.38(16) . . . . ?
O20 C20 C21 C26 -10.95(19) . . . . ?
O19 C20 C21 C26 167.08(11) . . . . ?
C26 C21 C22 C23 -0.26(19) . . . . ?
C20 C21 C22 C23 177.11(11) . . . . ?
C21 C22 C23 C24 -0.24(18) . . . . ?
C22 C23 C24 C25 0.54(19) . . . . ?
C22 C23 C24 N24 -177.28(11) . . . . ?
C25 C24 N24 O24 -169.54(11) . . . . ?
C23 C24 N24 O24 8.39(17) . . . . ?
C25 C24 N24 O25 9.57(17) . . . . ?
C23 C24 N24 O25 -172.49(12) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
N24 C24 C25 C26 177.50(11) . . . . ?
C24 C25 C26 C21 -0.2(2) . . . . ?
C22 C21 C26 C25 0.48(19) . . . . ?
C20 C21 C26 C25 -177.03(12) . . . . ?
C3 O3 C27 C28 36.02(12) . . . . ?
C3 O4 C28 C27 13.52(13) . . . . ?
O3 C27 C28 O4 -30.13(12) . . . . ?
C9 C10 C29 C30 -128.79(12) . . . . ?
C1 C10 C29 C30 103.33(12) . . . . ?
C9 C10 C29 C34 51.41(14) . . . . ?
C1 C10 C29 C34 -76.47(13) . . . . ?
C34 C29 C30 C31 0.60(18) . . . . ?
C10 C29 C30 C31 -179.20(11) . . . . ?
C29 C30 C31 C32 -0.49(19) . . . . ?
C30 C31 C32 C33 -0.3(2) . . . . ?
C31 C32 C33 C34 1.0(2) . . . . ?
C32 C33 C34 C29 -0.9(2) . . . . ?
C30 C29 C34 C33 0.11(18) . . . . ?
C10 C29 C34 C33 179.91(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C23 H23 O17 0.946(17) 2.524(17) 3.1963(17) 128.1(13) 1_455 yes

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.049

