# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_gy_445
_database_code_depnum_ccdc_archive 'CCDC 1524891'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2013-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   9.316(3)
_cell_length_b                   8.996(2)
_cell_length_c                   9.458(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.88(4)
_cell_angle_gamma                90.00
_cell_volume                     766.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0720
_cell_measurement_theta_min      4.1660
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.3200
_exptl_crystal_size_mid          0.2200
_exptl_crystal_size_min          0.2100
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2953
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.6763
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0715366000
_diffrn_orient_matrix_UB_12      0.0023304000
_diffrn_orient_matrix_UB_13      0.0133761000
_diffrn_orient_matrix_UB_21      0.0325345000
_diffrn_orient_matrix_UB_22      0.0101553000
_diffrn_orient_matrix_UB_23      0.0751203000
_diffrn_orient_matrix_UB_31      -0.0022433000
_diffrn_orient_matrix_UB_32      0.0783551000
_diffrn_orient_matrix_UB_33      -0.0100084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1980
_reflns_number_total             2402
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.0538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O -0.7477(2) -0.0894(3) -0.1387(3) 0.0699(6) Uani 1 1 d . . .
O2 O -1.1300(2) -0.2641(2) -0.4938(2) 0.0609(6) Uani 1 1 d . . .
O1 O -1.3541(2) -0.3108(3) -0.6344(2) 0.0698(6) Uani 1 1 d . . .
C8 C -1.2558(3) -0.3446(4) -0.5297(3) 0.0564(7) Uani 1 1 d . . .
C1 C -1.2454(3) -0.4676(4) -0.4268(3) 0.0555(7) Uani 1 1 d . . .
N1 N -0.7090(3) -0.4569(3) -0.2426(3) 0.0708(8) Uani 1 1 d . . .
C12 C -0.7925(3) -0.2258(4) -0.1997(3) 0.0591(8) Uani 1 1 d . . .
C2 C -1.3198(3) -0.5955(4) -0.4489(4) 0.0602(8) Uani 1 1 d . . .
C6 C -1.1198(3) -0.4307(3) -0.2969(3) 0.0551(7) Uani 1 1 d . . .
C7 C -1.0228(3) -0.3361(4) -0.3734(3) 0.0542(7) Uani 1 1 d . . .
H7 H -0.9589 -0.4020 -0.4130 0.065 Uiso 1 1 calc R . .
O4 O -0.6051(3) -0.5679(3) -0.1941(3) 0.0957(9) Uani 1 1 d . . .
H4 H -0.6275 -0.6414 -0.2465 0.144 Uiso 1 1 calc R . .
C15 C -0.6861(4) -0.3457(4) -0.1576(4) 0.0650(8) Uani 1 1 d . . .
C9 C -0.9312(3) -0.2147(4) -0.2883(3) 0.0572(7) Uani 1 1 d . . .
C11 C -0.8606(5) 0.0069(4) -0.1928(4) 0.0745(10) Uani 1 1 d . . .
H11 H -0.8595 0.1075 -0.1698 0.089 Uiso 1 1 calc R . .
C4 C -1.1638(4) -0.6814(4) -0.2037(5) 0.0805(11) Uani 1 1 d . . .
H4A H -1.1163 -0.7720 -0.1594 0.097 Uiso 1 1 calc R . .
H4B H -1.2137 -0.6366 -0.1361 0.097 Uiso 1 1 calc R . .
C13 C -1.4467(4) -0.6259(5) -0.5780(4) 0.0831(11) Uani 1 1 d . . .
H13A H -1.4390 -0.5633 -0.6580 0.125 Uiso 1 1 calc R . .
H13B H -1.5384 -0.6058 -0.5532 0.125 Uiso 1 1 calc R . .
H13C H -1.4444 -0.7283 -0.6062 0.125 Uiso 1 1 calc R . .
C10 C -0.9729(4) -0.0635(4) -0.2833(4) 0.0709(9) Uani 1 1 d . . .
H10 H -1.0624 -0.0213 -0.3340 0.085 Uiso 1 1 calc R . .
C3 C -1.2763(4) -0.7191(4) -0.3431(4) 0.0769(10) Uani 1 1 d . . .
H3A H -1.2372 -0.7993 -0.3907 0.092 Uiso 1 1 calc R . .
H3B H -1.3649 -0.7560 -0.3188 0.092 Uiso 1 1 calc R . .
C14 C -1.1766(4) -0.3362(5) -0.1894(4) 0.0757(10) Uani 1 1 d . . .
H14A H -1.2487 -0.3915 -0.1546 0.113 Uiso 1 1 calc R . .
H14B H -1.2217 -0.2475 -0.2374 0.113 Uiso 1 1 calc R . .
H14C H -1.0951 -0.3098 -0.1083 0.113 Uiso 1 1 calc R . .
C5 C -1.0447(3) -0.5740(4) -0.2289(4) 0.0715(9) Uani 1 1 d . . .
H5A H -0.9738 -0.5521 -0.1366 0.086 Uiso 1 1 calc R . .
H5B H -0.9916 -0.6191 -0.2937 0.086 Uiso 1 1 calc R . .
C16 C -0.5614(5) -0.3303(7) -0.0263(6) 0.121(2) Uani 1 1 d . . .
H16A H -0.4812 -0.3935 -0.0352 0.181 Uiso 1 1 calc R . .
H16B H -0.5934 -0.3584 0.0587 0.181 Uiso 1 1 calc R . .
H16C H -0.5283 -0.2288 -0.0167 0.181 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
O3 C12 1.374(4) . ?
O3 C11 1.357(4) . ?
O2 C8 1.345(4) . ?
O2 C7 1.459(3) . ?
O1 C8 1.202(3) . ?
C8 C1 1.461(5) . ?
C1 C2 1.332(4) . ?
C1 C6 1.500(4) . ?
N1 O4 1.384(3) . ?
N1 C15 1.267(4) . ?
C12 C15 1.450(5) . ?
C12 C9 1.351(4) . ?
C2 C13 1.491(4) . ?
C2 C3 1.481(5) . ?
C6 C7 1.549(4) . ?
C6 C14 1.521(5) . ?
C6 C5 1.528(4) . ?
C7 H7 0.9800 . ?
C7 C9 1.488(5) . ?
O4 H4 0.8200 . ?
C15 C16 1.473(5) . ?
C9 C10 1.419(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.330(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.497(5) . ?
C4 C5 1.535(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 O3 C12 106.8(3) . . ?
C8 O2 C7 109.6(2) . . ?
O2 C8 C1 109.6(2) . . ?
O1 C8 O2 120.1(3) . . ?
O1 C8 C1 130.3(3) . . ?
C8 C1 C6 106.4(3) . . ?
C2 C1 C8 127.4(3) . . ?
C2 C1 C6 125.8(3) . . ?
C15 N1 O4 111.7(3) . . ?
O3 C12 C15 115.9(3) . . ?
C9 C12 O3 109.5(3) . . ?
C9 C12 C15 134.6(3) . . ?
C1 C2 C13 123.9(3) . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 C13 115.9(3) . . ?
C1 C6 C7 99.5(2) . . ?
C1 C6 C14 109.9(3) . . ?
C1 C6 C5 109.6(3) . . ?
C14 C6 C7 110.5(3) . . ?
C14 C6 C5 113.0(3) . . ?
C5 C6 C7 113.6(2) . . ?
O2 C7 C6 104.1(2) . . ?
O2 C7 H7 109.3 . . ?
O2 C7 C9 106.2(3) . . ?
C6 C7 H7 109.3 . . ?
C9 C7 C6 118.2(3) . . ?
C9 C7 H7 109.3 . . ?
N1 O4 H4 109.5 . . ?
N1 C15 C12 114.9(3) . . ?
N1 C15 C16 125.3(4) . . ?
C12 C15 C16 119.8(3) . . ?
C12 C9 C7 127.2(3) . . ?
C12 C9 C10 106.0(3) . . ?
C10 C9 C7 126.7(3) . . ?
O3 C11 H11 124.9 . . ?
C10 C11 O3 110.1(3) . . ?
C10 C11 H11 124.9 . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 112.1(3) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.5(3) . . ?
C11 C10 H10 126.2 . . ?
C2 C3 C4 115.7(3) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C5 C4 109.0(2) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O3 C12 C15 N1 -160.9(3) . . . . ?
O3 C12 C15 C16 17.7(5) . . . . ?
O3 C12 C9 C7 -178.7(3) . . . . ?
O3 C12 C9 C10 0.9(4) . . . . ?
O3 C11 C10 C9 0.2(4) . . . . ?
O2 C8 C1 C2 -156.3(3) . . . . ?
O2 C8 C1 C6 16.6(3) . . . . ?
O2 C7 C9 C12 -156.6(3) . . . . ?
O2 C7 C9 C10 23.9(4) . . . . ?
O1 C8 C1 C2 22.7(5) . . . . ?
O1 C8 C1 C6 -164.4(3) . . . . ?
C8 O2 C7 C6 -23.9(3) . . . . ?
C8 O2 C7 C9 -149.4(2) . . . . ?
C8 C1 C2 C13 -10.1(5) . . . . ?
C8 C1 C2 C3 168.9(3) . . . . ?
C8 C1 C6 C7 -29.1(3) . . . . ?
C8 C1 C6 C14 86.9(3) . . . . ?
C8 C1 C6 C5 -148.4(3) . . . . ?
C1 C2 C3 C4 9.3(5) . . . . ?
C1 C6 C7 O2 31.6(3) . . . . ?
C1 C6 C7 C9 149.1(3) . . . . ?
C1 C6 C5 C4 -50.7(4) . . . . ?
C12 O3 C11 C10 0.4(4) . . . . ?
C12 C9 C10 C11 -0.7(4) . . . . ?
C2 C1 C6 C7 144.0(3) . . . . ?
C2 C1 C6 C14 -100.1(4) . . . . ?
C2 C1 C6 C5 24.6(4) . . . . ?
C6 C1 C2 C13 178.3(3) . . . . ?
C6 C1 C2 C3 -2.7(5) . . . . ?
C6 C7 C9 C12 87.0(4) . . . . ?
C6 C7 C9 C10 -92.5(4) . . . . ?
C7 O2 C8 O1 -174.0(3) . . . . ?
C7 O2 C8 C1 5.2(3) . . . . ?
C7 C6 C5 C4 -161.0(3) . . . . ?
C7 C9 C10 C11 178.9(3) . . . . ?
O4 N1 C15 C12 -178.8(3) . . . . ?
O4 N1 C15 C16 2.7(6) . . . . ?
C15 C12 C9 C7 1.3(6) . . . . ?
C15 C12 C9 C10 -179.1(4) . . . . ?
C9 C12 C15 N1 19.1(6) . . . . ?
C9 C12 C15 C16 -162.3(4) . . . . ?
C11 O3 C12 C15 179.2(3) . . . . ?
C11 O3 C12 C9 -0.8(4) . . . . ?
C13 C2 C3 C4 -171.7(3) . . . . ?
C3 C4 C5 C6 59.6(4) . . . . ?
C14 C6 C7 O2 -83.9(3) . . . . ?
C14 C6 C7 C9 33.6(4) . . . . ?
C14 C6 C5 C4 72.1(4) . . . . ?
C5 C6 C7 O2 147.9(3) . . . . ?
C5 C6 C7 C9 -94.6(3) . . . . ?
C5 C4 C3 C2 -38.1(5) . . . . ?

####################################################################### 
# 
# 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_gy_388_2
_database_code_depnum_ccdc_archive 'CCDC 1524890'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2013-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   10.4720(7)
_cell_length_b                   17.0011(11)
_cell_length_c                   17.1489(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3053.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6420
_cell_measurement_theta_min      3.8800
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8090
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.8050
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0282366000
_diffrn_orient_matrix_UB_12      -0.0351974000
_diffrn_orient_matrix_UB_13      0.0140062000
_diffrn_orient_matrix_UB_21      0.0608590000
_diffrn_orient_matrix_UB_22      -0.0182780000
_diffrn_orient_matrix_UB_23      0.0004459000
_diffrn_orient_matrix_UB_31      0.0094650000
_diffrn_orient_matrix_UB_32      0.0128512000
_diffrn_orient_matrix_UB_33      0.0389329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2966
_reflns_number_total             5563
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.0221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C26(H26), C28(H28)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2604(4) -0.7930(2) -0.21192(18) 0.0874(12) Uani 1 1 d . . .
O2 O -0.2477(3) -0.77837(19) -0.08336(16) 0.0642(9) Uani 1 1 d . . .
O3 O -0.2710(3) -0.7839(2) 0.18086(16) 0.0702(10) Uani 1 1 d . . .
O4 O -0.5539(4) -0.8663(3) 0.31939(18) 0.1037(14) Uani 1 1 d . . .
H4 H -0.5365 -0.8597 0.3656 0.155 Uiso 1 1 calc R . .
O5 O -0.5289(4) -0.8983(2) 0.92983(17) 0.0800(11) Uani 1 1 d . . .
O6 O -0.5457(3) -0.89604(18) 0.80003(15) 0.0619(9) Uani 1 1 d . . .
O7 O -0.5392(4) -0.8877(2) 0.53546(16) 0.0760(10) Uani 1 1 d . . .
O8 O -0.2915(4) -0.7788(3) 0.38806(18) 0.1050(15) Uani 1 1 d . . .
H8 H -0.3098 -0.7870 0.3423 0.157 Uiso 1 1 calc R . .
N1 N -0.4518(5) -0.8384(2) 0.2726(2) 0.0787(14) Uani 1 1 d . . .
N2 N -0.3809(5) -0.8166(3) 0.4366(2) 0.0852(14) Uani 1 1 d . . .
C1 C -0.5144(4) -1.0199(3) 0.8528(2) 0.0559(12) Uani 1 1 d . . .
C2 C -0.5428(5) -1.0775(3) 0.9002(3) 0.0738(15) Uani 1 1 d . . .
C3 C -0.5476(7) -1.1605(3) 0.8696(3) 0.096(2) Uani 1 1 d . . .
H3A H -0.6356 -1.1784 0.8709 0.115 Uiso 1 1 calc R . .
H3B H -0.4990 -1.1940 0.9045 0.115 Uiso 1 1 calc R . .
C4 C -0.4968(6) -1.1717(3) 0.7874(3) 0.0820(17) Uani 1 1 d . . .
H4A H -0.4044 -1.1747 0.7888 0.098 Uiso 1 1 calc R . .
H4B H -0.5289 -1.2208 0.7662 0.098 Uiso 1 1 calc R . .
C5 C -0.5377(6) -1.1040(3) 0.7355(3) 0.0740(15) Uani 1 1 d . . .
H5A H -0.6302 -1.1017 0.7332 0.089 Uiso 1 1 calc R . .
H5B H -0.5059 -1.1124 0.6830 0.089 Uiso 1 1 calc R . .
C6 C -0.4858(5) -1.0267(3) 0.7671(2) 0.0526(11) Uani 1 1 d . . .
C7 C -0.5600(5) -0.9542(3) 0.7378(2) 0.0572(12) Uani 1 1 d . . .
H7 H -0.6505 -0.9687 0.7354 0.069 Uiso 1 1 calc R . .
C8 C -0.5282(5) -0.9346(3) 0.8688(3) 0.0646(13) Uani 1 1 d . . .
C9 C -0.5257(5) -0.9180(3) 0.6620(2) 0.0575(12) Uani 1 1 d . . .
C10 C -0.4135(5) -0.8773(3) 0.6392(2) 0.0608(13) Uani 1 1 d . . .
H10 H -0.3448 -0.8648 0.6713 0.073 Uiso 1 1 calc R . .
C11 C -0.4244(5) -0.8600(3) 0.5626(3) 0.0630(13) Uani 1 1 d . . .
C12 C -0.5964(6) -0.9229(3) 0.5975(3) 0.0753(16) Uani 1 1 d . . .
H12 H -0.6756 -0.9475 0.5952 0.090 Uiso 1 1 calc R . .
C13 C -0.5789(7) -1.0685(4) 0.9850(2) 0.119(3) Uani 1 1 d . . .
H13A H -0.5685 -1.0146 1.0004 0.178 Uiso 1 1 calc R . .
H13B H -0.5249 -1.1013 1.0164 0.178 Uiso 1 1 calc R . .
H13C H -0.6664 -1.0839 0.9921 0.178 Uiso 1 1 calc R . .
C14 C -0.3405(5) -1.0195(3) 0.7530(2) 0.0660(14) Uani 1 1 d . . .
H14A H -0.3110 -0.9697 0.7723 0.099 Uiso 1 1 calc R . .
H14B H -0.3233 -1.0230 0.6981 0.099 Uiso 1 1 calc R . .
H14C H -0.2971 -1.0612 0.7798 0.099 Uiso 1 1 calc R . .
C15 C -0.3410(6) -0.8208(3) 0.5081(3) 0.0674(14) Uani 1 1 d . . .
C16 C -0.2155(6) -0.7910(4) 0.5362(3) 0.099(2) Uani 1 1 d . . .
H16A H -0.1485 -0.8240 0.5165 0.148 Uiso 1 1 calc R . .
H16B H -0.2141 -0.7917 0.5922 0.148 Uiso 1 1 calc R . .
H16C H -0.2031 -0.7381 0.5181 0.148 Uiso 1 1 calc R . .
C17 C -0.0956(5) -0.8596(3) -0.1362(2) 0.0568(12) Uani 1 1 d . . .
C18 C -0.0051(5) -0.8807(3) -0.1877(3) 0.0675(14) Uani 1 1 d . . .
C19 C 0.1130(5) -0.9203(3) -0.1597(3) 0.0825(16) Uani 1 1 d . . .
H19A H 0.1850 -0.8863 -0.1710 0.099 Uiso 1 1 calc R . .
H19B H 0.1246 -0.9682 -0.1897 0.099 Uiso 1 1 calc R . .
C20 C 0.1175(5) -0.9418(4) -0.0730(3) 0.0856(17) Uani 1 1 d . . .
H20A H 0.0797 -0.9934 -0.0657 0.103 Uiso 1 1 calc R . .
H20B H 0.2058 -0.9446 -0.0562 0.103 Uiso 1 1 calc R . .
C21 C 0.0465(5) -0.8822(3) -0.0227(3) 0.0720(14) Uani 1 1 d . . .
H21A H 0.0885 -0.8314 -0.0262 0.086 Uiso 1 1 calc R . .
H21B H 0.0483 -0.8989 0.0313 0.086 Uiso 1 1 calc R . .
C22 C -0.0921(4) -0.8746(3) -0.0502(2) 0.0526(11) Uani 1 1 d . . .
C23 C -0.1563(5) -0.7988(3) -0.0211(2) 0.0563(12) Uani 1 1 d . . .
H23 H -0.0915 -0.7573 -0.0179 0.068 Uiso 1 1 calc R . .
C24 C -0.2077(5) -0.8092(3) -0.1517(3) 0.0656(14) Uani 1 1 d . . .
C25 C -0.2279(5) -0.8011(3) 0.0540(2) 0.0534(12) Uani 1 1 d . . .
C26 C -0.3475(5) -0.8373(3) 0.0714(2) 0.0593(13) Uani 1 1 d . . .
H26 H -0.4003 -0.8638 0.0365 0.071 Uiso 1 1 calc R . .
C27 C -0.3697(5) -0.8259(3) 0.1487(3) 0.0592(13) Uani 1 1 d . . .
C28 C -0.1877(5) -0.7697(3) 0.1218(3) 0.0688(15) Uani 1 1 d . . .
H28 H -0.1119 -0.7417 0.1275 0.083 Uiso 1 1 calc R . .
C29 C -0.0106(6) -0.8645(3) -0.2736(2) 0.096(2) Uani 1 1 d . . .
H29A H -0.0738 -0.8249 -0.2837 0.144 Uiso 1 1 calc R . .
H29B H -0.0328 -0.9118 -0.3009 0.144 Uiso 1 1 calc R . .
H29C H 0.0713 -0.8463 -0.2912 0.144 Uiso 1 1 calc R . .
C30 C -0.1696(5) -0.9485(3) -0.0313(3) 0.0681(14) Uani 1 1 d . . .
H30A H -0.1353 -0.9924 -0.0595 0.102 Uiso 1 1 calc R . .
H30B H -0.2570 -0.9405 -0.0461 0.102 Uiso 1 1 calc R . .
H30C H -0.1651 -0.9589 0.0237 0.102 Uiso 1 1 calc R . .
C31 C -0.4708(6) -0.8515(3) 0.2002(3) 0.0699(14) Uani 1 1 d . . .
C32 C -0.5834(6) -0.8925(3) 0.1663(3) 0.0918(18) Uani 1 1 d . . .
H32A H -0.5775 -0.9478 0.1768 0.138 Uiso 1 1 calc R . .
H32B H -0.5852 -0.8841 0.1109 0.138 Uiso 1 1 calc R . .
H32C H -0.6601 -0.8719 0.1891 0.138 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
O1 C24 1.203(5) . ?
O2 C23 1.476(5) . ?
O2 C24 1.351(5) . ?
O3 C27 1.372(5) . ?
O3 C28 1.358(5) . ?
O4 H4 0.8200 . ?
O4 N1 1.418(5) . ?
O5 C8 1.215(5) . ?
O6 C7 1.462(5) . ?
O6 C8 1.362(5) . ?
O7 C11 1.372(6) . ?
O7 C12 1.360(5) . ?
O8 H8 0.8200 . ?
O8 N2 1.408(5) . ?
N1 C31 1.276(5) . ?
N2 C15 1.298(6) . ?
C1 C2 1.307(6) . ?
C1 C6 1.504(6) . ?
C1 C8 1.484(6) . ?
C2 C3 1.507(7) . ?
C2 C13 1.511(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.517(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.522(6) . ?
C6 C7 1.540(6) . ?
C6 C14 1.546(6) . ?
C7 H7 0.9800 . ?
C7 C9 1.483(5) . ?
C9 C10 1.419(6) . ?
C9 C12 1.334(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.352(5) . ?
C11 C15 1.442(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.488(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.345(6) . ?
C17 C22 1.497(5) . ?
C17 C24 1.477(7) . ?
C18 C19 1.487(7) . ?
C18 C29 1.499(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.524(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.531(6) . ?
C22 C23 1.537(6) . ?
C22 C30 1.530(6) . ?
C23 H23 0.9800 . ?
C23 C25 1.490(6) . ?
C25 C26 1.428(6) . ?
C25 C28 1.347(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.360(6) . ?
C27 C31 1.446(7) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.488(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
C24 O2 C23 109.6(4) . . ?
C28 O3 C27 106.1(3) . . ?
N1 O4 H4 109.5 . . ?
C8 O6 C7 108.7(3) . . ?
C12 O7 C11 105.8(4) . . ?
N2 O8 H8 109.5 . . ?
C31 N1 O4 112.0(5) . . ?
C15 N2 O8 111.7(5) . . ?
C2 C1 C6 126.6(5) . . ?
C2 C1 C8 126.5(4) . . ?
C8 C1 C6 106.0(4) . . ?
C1 C2 C3 119.5(4) . . ?
C1 C2 C13 125.5(5) . . ?
C3 C2 C13 115.0(5) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C2 C3 C4 115.4(4) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.6(5) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.2(4) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C1 C6 C5 110.0(4) . . ?
C1 C6 C7 99.0(3) . . ?
C1 C6 C14 110.1(4) . . ?
C5 C6 C7 113.2(4) . . ?
C5 C6 C14 111.3(4) . . ?
C7 C6 C14 112.5(4) . . ?
O6 C7 C6 104.6(3) . . ?
O6 C7 H7 107.5 . . ?
O6 C7 C9 109.5(4) . . ?
C6 C7 H7 107.5 . . ?
C9 C7 C6 119.7(4) . . ?
C9 C7 H7 107.5 . . ?
O5 C8 O6 120.1(5) . . ?
O5 C8 C1 131.1(4) . . ?
O6 C8 C1 108.8(4) . . ?
C10 C9 C7 130.1(4) . . ?
C12 C9 C7 124.6(5) . . ?
C12 C9 C10 105.2(4) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 C9 107.7(4) . . ?
C11 C10 H10 126.1 . . ?
O7 C11 C15 118.0(4) . . ?
C10 C11 O7 109.2(4) . . ?
C10 C11 C15 132.8(5) . . ?
O7 C12 H12 123.9 . . ?
C9 C12 O7 112.1(5) . . ?
C9 C12 H12 123.9 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C11 116.3(5) . . ?
N2 C15 C16 124.9(5) . . ?
C11 C15 C16 118.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 125.8(4) . . ?
C18 C17 C24 126.6(4) . . ?
C24 C17 C22 107.2(4) . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 C29 124.7(5) . . ?
C19 C18 C29 115.7(5) . . ?
C18 C19 H19A 108.1 . . ?
C18 C19 H19B 108.1 . . ?
C18 C19 C20 116.6(4) . . ?
H19A C19 H19B 107.3 . . ?
C20 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 112.0(4) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
C20 C21 C22 110.1(4) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C17 C22 C21 109.9(4) . . ?
C17 C22 C23 99.6(3) . . ?
C17 C22 C30 109.6(4) . . ?
C21 C22 C23 112.7(4) . . ?
C30 C22 C21 111.6(4) . . ?
C30 C22 C23 112.8(4) . . ?
O2 C23 C22 104.3(3) . . ?
O2 C23 H23 108.6 . . ?
O2 C23 C25 107.7(4) . . ?
C22 C23 H23 108.6 . . ?
C25 C23 C22 118.7(4) . . ?
C25 C23 H23 108.6 . . ?
O1 C24 O2 120.9(5) . . ?
O1 C24 C17 130.7(5) . . ?
O2 C24 C17 108.4(4) . . ?
C26 C25 C23 129.3(4) . . ?
C28 C25 C23 125.3(5) . . ?
C28 C25 C26 105.3(4) . . ?
C25 C26 H26 126.5 . . ?
C27 C26 C25 107.0(4) . . ?
C27 C26 H26 126.5 . . ?
O3 C27 C31 117.5(4) . . ?
C26 C27 O3 109.7(4) . . ?
C26 C27 C31 132.7(5) . . ?
O3 C28 H28 124.1 . . ?
C25 C28 O3 111.9(5) . . ?
C25 C28 H28 124.1 . . ?
C18 C29 H29A 109.5 . . ?
C18 C29 H29B 109.5 . . ?
C18 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
C22 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 C31 C27 115.3(5) . . ?
N1 C31 C32 125.8(5) . . ?
C27 C31 C32 118.8(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C23 C25 C26 46.4(6) . . . . ?
O2 C23 C25 C28 -136.0(5) . . . . ?
O3 C27 C31 N1 -6.2(7) . . . . ?
O3 C27 C31 C32 175.9(4) . . . . ?
O4 N1 C31 C27 -179.1(4) . . . . ?
O4 N1 C31 C32 -1.4(7) . . . . ?
O6 C7 C9 C10 53.4(6) . . . . ?
O6 C7 C9 C12 -131.5(5) . . . . ?
O7 C11 C15 N2 -1.6(7) . . . . ?
O7 C11 C15 C16 -179.4(5) . . . . ?
O8 N2 C15 C11 -178.8(4) . . . . ?
O8 N2 C15 C16 -1.1(7) . . . . ?
C1 C2 C3 C4 9.8(9) . . . . ?
C1 C6 C7 O6 35.0(4) . . . . ?
C1 C6 C7 C9 158.1(4) . . . . ?
C2 C1 C6 C5 19.6(7) . . . . ?
C2 C1 C6 C7 138.4(5) . . . . ?
C2 C1 C6 C14 -103.5(6) . . . . ?
C2 C1 C8 O5 25.4(10) . . . . ?
C2 C1 C8 O6 -152.8(5) . . . . ?
C2 C3 C4 C5 -40.1(7) . . . . ?
C3 C4 C5 C6 60.3(6) . . . . ?
C4 C5 C6 C1 -49.0(5) . . . . ?
C4 C5 C6 C7 -158.8(4) . . . . ?
C4 C5 C6 C14 73.3(5) . . . . ?
C5 C6 C7 O6 151.5(4) . . . . ?
C5 C6 C7 C9 -85.5(5) . . . . ?
C6 C1 C2 C3 0.6(9) . . . . ?
C6 C1 C2 C13 -176.1(5) . . . . ?
C6 C1 C8 O5 -165.1(5) . . . . ?
C6 C1 C8 O6 16.6(5) . . . . ?
C6 C7 C9 C10 -67.2(6) . . . . ?
C6 C7 C9 C12 107.9(6) . . . . ?
C7 O6 C8 O5 -171.5(5) . . . . ?
C7 O6 C8 C1 7.0(5) . . . . ?
C7 C9 C10 C11 176.1(4) . . . . ?
C7 C9 C12 O7 -176.9(4) . . . . ?
C8 O6 C7 C6 -27.3(5) . . . . ?
C8 O6 C7 C9 -156.7(4) . . . . ?
C8 C1 C2 C3 168.0(5) . . . . ?
C8 C1 C2 C13 -8.7(9) . . . . ?
C8 C1 C6 C5 -149.9(4) . . . . ?
C8 C1 C6 C7 -31.0(5) . . . . ?
C8 C1 C6 C14 87.0(5) . . . . ?
C9 C10 C11 O7 0.2(5) . . . . ?
C9 C10 C11 C15 -179.0(5) . . . . ?
C10 C9 C12 O7 -0.8(6) . . . . ?
C10 C11 C15 N2 177.6(5) . . . . ?
C10 C11 C15 C16 -0.3(9) . . . . ?
C11 O7 C12 C9 1.0(6) . . . . ?
C12 O7 C11 C10 -0.7(5) . . . . ?
C12 O7 C11 C15 178.7(4) . . . . ?
C12 C9 C10 C11 0.4(5) . . . . ?
C13 C2 C3 C4 -173.1(5) . . . . ?
C14 C6 C7 O6 -81.2(4) . . . . ?
C14 C6 C7 C9 41.8(6) . . . . ?
C17 C18 C19 C20 5.8(8) . . . . ?
C17 C22 C23 O2 32.1(4) . . . . ?
C17 C22 C23 C25 151.8(4) . . . . ?
C18 C17 C22 C21 25.8(7) . . . . ?
C18 C17 C22 C23 144.2(5) . . . . ?
C18 C17 C22 C30 -97.3(6) . . . . ?
C18 C17 C24 O1 20.8(9) . . . . ?
C18 C17 C24 O2 -157.7(5) . . . . ?
C18 C19 C20 C21 -33.5(7) . . . . ?
C19 C20 C21 C22 56.8(6) . . . . ?
C20 C21 C22 C17 -51.6(5) . . . . ?
C20 C21 C22 C23 -161.6(4) . . . . ?
C20 C21 C22 C30 70.3(5) . . . . ?
C21 C22 C23 O2 148.4(4) . . . . ?
C21 C22 C23 C25 -91.8(5) . . . . ?
C22 C17 C18 C19 -2.3(8) . . . . ?
C22 C17 C18 C29 -179.6(4) . . . . ?
C22 C17 C24 O1 -166.2(5) . . . . ?
C22 C17 C24 O2 15.4(5) . . . . ?
C22 C23 C25 C26 -71.6(6) . . . . ?
C22 C23 C25 C28 106.0(6) . . . . ?
C23 O2 C24 O1 -172.1(5) . . . . ?
C23 O2 C24 C17 6.6(5) . . . . ?
C23 C25 C26 C27 177.3(4) . . . . ?
C23 C25 C28 O3 -177.4(4) . . . . ?
C24 O2 C23 C22 -25.2(5) . . . . ?
C24 O2 C23 C25 -152.2(4) . . . . ?
C24 C17 C18 C19 169.6(5) . . . . ?
C24 C17 C18 C29 -7.7(8) . . . . ?
C24 C17 C22 C21 -147.4(4) . . . . ?
C24 C17 C22 C23 -29.0(5) . . . . ?
C24 C17 C22 C30 89.5(5) . . . . ?
C25 C26 C27 O3 0.4(5) . . . . ?
C25 C26 C27 C31 -176.9(5) . . . . ?
C26 C25 C28 O3 0.7(6) . . . . ?
C26 C27 C31 N1 170.9(5) . . . . ?
C26 C27 C31 C32 -7.0(9) . . . . ?
C27 O3 C28 C25 -0.4(6) . . . . ?
C28 O3 C27 C26 0.0(5) . . . . ?
C28 O3 C27 C31 177.7(4) . . . . ?
C28 C25 C26 C27 -0.7(5) . . . . ?
C29 C18 C19 C20 -176.6(4) . . . . ?
C30 C22 C23 O2 -84.1(4) . . . . ?
C30 C22 C23 C25 35.7(5) . . . . ?

####################################################################### 
# 
# 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_gy_455
_database_code_depnum_ccdc_archive 'CCDC 1524893'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2015-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H22 F N O5'
_chemical_formula_sum            'C23 H22 F N O5'
_chemical_formula_weight         411.41
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

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

_cell_length_a                   5.7078(4)
_cell_length_b                   17.2420(12)
_cell_length_c                   21.441(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2110.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.3630
_cell_measurement_theta_min      3.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.1169
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5598
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.527
_diffrn_reflns_theta_min         3.666
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   13.50   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   56.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -38.0000 -120.0000 68
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0633730000
_diffrn_orient_matrix_UB_12      -0.0100135000
_diffrn_orient_matrix_UB_13      -0.0273623000
_diffrn_orient_matrix_UB_21      0.0255407000
_diffrn_orient_matrix_UB_22      -0.0368058000
_diffrn_orient_matrix_UB_23      0.0130264000
_diffrn_orient_matrix_UB_31      -0.1037956000
_diffrn_orient_matrix_UB_32      -0.0152066000
_diffrn_orient_matrix_UB_33      -0.0134201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.660
_reflns_number_gt                1668
_reflns_number_total             4303
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_coef       0.0078(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.0739
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0474P)²+0.1238P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.2147
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.1542(14) 1.1581(4) 0.0756(3) 0.135(3) Uani 1 1 d . . . . .
O2 O 0.1960(10) 1.1736(3) 0.1789(3) 0.0860(17) Uani 1 1 d . . . . .
O3 O 0.8160(12) 1.0527(4) 0.2784(3) 0.0997(19) Uani 1 1 d . . . . .
O4 O 0.4774(9) 0.8695(3) 0.1586(2) 0.0727(14) Uani 1 1 d . . . . .
O5 O 0.3454(11) 0.7691(3) 0.1036(3) 0.0916(18) Uani 1 1 d . . . . .
F1 F -0.5806(13) 1.4174(4) 0.1391(3) 0.183(3) Uani 1 1 d . . . . .
N1 N 0.3797(13) 1.1168(4) 0.1755(3) 0.085(2) Uani 1 1 d . . . . .
C1 C -0.1778(19) 1.2801(5) 0.0760(4) 0.100(3) Uani 1 1 d . . . . .
H1 H -0.1226 1.2630 0.0376 0.120 Uiso 1 1 calc R . . . .
C2 C -0.348(2) 1.3371(6) 0.0780(4) 0.113(3) Uani 1 1 d . . . . .
H2 H -0.4101 1.3588 0.0420 0.136 Uiso 1 1 calc R . . . .
C3 C -0.4187(19) 1.3598(6) 0.1361(5) 0.112(4) Uani 1 1 d . . . . .
C4 C -0.3356(17) 1.3293(5) 0.1900(4) 0.100(3) Uani 1 1 d . . . . .
H4 H -0.3917 1.3462 0.2284 0.120 Uiso 1 1 calc R . . . .
C5 C -0.1680(17) 1.2734(5) 0.1865(4) 0.089(3) Uani 1 1 d . . . . .
H5 H -0.1068 1.2521 0.2229 0.107 Uiso 1 1 calc R . . . .
C6 C -0.0892(15) 1.2483(5) 0.1298(4) 0.076(2) Uani 1 1 d . . . . .
C7 C 0.0956(18) 1.1898(6) 0.1220(4) 0.093(3) Uani 1 1 d . . . . .
C8 C 0.4771(17) 1.1079(5) 0.2290(4) 0.082(2) Uani 1 1 d . . . . .
C9 C 0.6507(15) 1.0476(5) 0.2309(4) 0.079(2) Uani 1 1 d . . . . .
C10 C 0.9525(18) 0.9881(6) 0.2733(4) 0.101(3) Uani 1 1 d . . . . .
H10 H 1.0788 0.9769 0.2991 0.121 Uiso 1 1 calc R . . . .
C11 C 0.8803(15) 0.9429(6) 0.2259(4) 0.097(3) Uani 1 1 d . . . . .
H11 H 0.9470 0.8962 0.2135 0.117 Uiso 1 1 calc R . . . .
C12 C 0.6812(14) 0.9802(5) 0.1982(4) 0.073(2) Uani 1 1 d . . . . .
C13 C 0.5386(12) 0.9512(4) 0.1458(3) 0.067(2) Uani 1 1 d . . . . .
H13 H 0.3927 0.9812 0.1449 0.081 Uiso 1 1 calc R . . . .
C14 C 0.4347(14) 0.8333(5) 0.1030(4) 0.071(2) Uani 1 1 d . . . . .
C15 C 0.5033(14) 0.8840(4) 0.0519(3) 0.0633(19) Uani 1 1 d . . . . .
C16 C 0.4381(14) 0.8804(5) -0.0069(4) 0.072(2) Uani 1 1 d . . . . .
C17 C 0.4891(18) 0.9453(6) -0.0512(4) 0.100(3) Uani 1 1 d . . . . .
H17A H 0.3410 0.9673 -0.0647 0.120 Uiso 1 1 calc R . . . .
H17B H 0.5650 0.9237 -0.0878 0.120 Uiso 1 1 calc R . . . .
C18 C 0.6414(19) 1.0109(6) -0.0264(4) 0.104(3) Uani 1 1 d . . . . .
H18A H 0.6082 1.0579 -0.0496 0.125 Uiso 1 1 calc R . . . .
H18B H 0.8051 0.9979 -0.0328 0.125 Uiso 1 1 calc R . . . .
C19 C 0.5973(17) 1.0252(5) 0.0431(4) 0.088(3) Uani 1 1 d . . . . .
H19A H 0.7009 1.0657 0.0581 0.106 Uiso 1 1 calc R . . . .
H19B H 0.4369 1.0421 0.0493 0.106 Uiso 1 1 calc R . . . .
C20 C 0.6411(12) 0.9507(4) 0.0794(3) 0.0645(19) Uani 1 1 d . . . . .
C21 C 0.4181(18) 1.1541(5) 0.2869(4) 0.106(3) Uani 1 1 d . . . . .
H21A H 0.4323 1.2084 0.2780 0.159 Uiso 1 1 calc GR . . . .
H21B H 0.5241 1.1403 0.3198 0.159 Uiso 1 1 calc GR . . . .
H21C H 0.2604 1.1428 0.2995 0.159 Uiso 1 1 calc GR . . . .
C22 C 0.9042(12) 0.9297(6) 0.0795(4) 0.098(3) Uani 1 1 d . . . . .
H22A H 0.9280 0.8835 0.1038 0.148 Uiso 1 1 calc GR . . . .
H22B H 0.9922 0.9716 0.0974 0.148 Uiso 1 1 calc GR . . . .
H22C H 0.9557 0.9209 0.0375 0.148 Uiso 1 1 calc GR . . . .
C23 C 0.2957(17) 0.8145(5) -0.0348(4) 0.102(3) Uani 1 1 d . . . . .
H23A H 0.2766 0.7742 -0.0044 0.152 Uiso 1 1 calc GR . . . .
H23B H 0.3759 0.7941 -0.0706 0.152 Uiso 1 1 calc GR . . . .
H23C H 0.1446 0.8335 -0.0472 0.152 Uiso 1 1 calc GR . . . .


_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
O1 C7 1.183(9) . ?
O2 N1 1.437(8) . ?
O2 C7 1.376(9) . ?
O3 C9 1.391(9) . ?
O3 C10 1.363(10) . ?
O4 C13 1.477(8) . ?
O4 C14 1.368(8) . ?
O5 C14 1.219(9) . ?
F1 C3 1.359(10) . ?
N1 C8 1.284(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(12) . ?
C1 C6 1.374(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(12) . ?
C3 C4 1.354(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.360(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(10) . ?
C6 C7 1.469(11) . ?
C8 C9 1.436(11) . ?
C8 C21 1.513(10) . ?
C9 C12 1.368(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.345(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.435(11) . ?
C12 C13 1.474(9) . ?
C13 H13 0.9800 . ?
C13 C20 1.540(9) . ?
C14 C15 1.455(10) . ?
C15 C16 1.314(9) . ?
C15 C20 1.513(10) . ?
C16 C17 1.498(10) . ?
C16 C23 1.520(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.521(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.532(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.523(10) . ?
C20 C22 1.545(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C7 O2 N1 113.3(6) . . ?
C10 O3 C9 106.1(7) . . ?
C14 O4 C13 108.4(6) . . ?
C8 N1 O2 110.6(7) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C6 C1 C2 121.1(9) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 C1 116.1(9) . . ?
C3 C2 H2 121.9 . . ?
F1 C3 C2 117.0(9) . . ?
C4 C3 F1 118.9(10) . . ?
C4 C3 C2 124.2(9) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(9) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(9) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 116.3(8) . . ?
C5 C6 C1 120.0(8) . . ?
C5 C6 C7 123.7(8) . . ?
O1 C7 O2 122.3(9) . . ?
O1 C7 C6 128.0(9) . . ?
O2 C7 C6 109.7(7) . . ?
N1 C8 C9 114.2(8) . . ?
N1 C8 C21 125.0(8) . . ?
C9 C8 C21 120.8(8) . . ?
O3 C9 C8 116.3(8) . . ?
C12 C9 O3 110.0(8) . . ?
C12 C9 C8 133.5(8) . . ?
O3 C10 H10 124.5 . . ?
C11 C10 O3 111.1(9) . . ?
C11 C10 H10 124.5 . . ?
C10 C11 H11 126.4 . . ?
C10 C11 C12 107.1(8) . . ?
C12 C11 H11 126.4 . . ?
C9 C12 C11 105.7(7) . . ?
C9 C12 C13 127.4(7) . . ?
C11 C12 C13 126.9(7) . . ?
O4 C13 H13 107.8 . . ?
O4 C13 C20 104.8(5) . . ?
C12 C13 O4 108.2(6) . . ?
C12 C13 H13 107.8 . . ?
C12 C13 C20 119.8(6) . . ?
C20 C13 H13 107.8 . . ?
O4 C14 C15 109.5(7) . . ?
O5 C14 O4 118.6(7) . . ?
O5 C14 C15 131.8(8) . . ?
C14 C15 C20 107.6(6) . . ?
C16 C15 C14 128.0(8) . . ?
C16 C15 C20 123.9(7) . . ?
C15 C16 C17 121.2(8) . . ?
C15 C16 C23 124.4(8) . . ?
C17 C16 C23 114.3(7) . . ?
C16 C17 H17A 108.2 . . ?
C16 C17 H17B 108.2 . . ?
C16 C17 C18 116.4(7) . . ?
H17A C17 H17B 107.3 . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C17 C18 C19 111.4(7) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 C18 109.5(7) . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C13 C20 C22 111.7(7) . . ?
C15 C20 C13 99.7(6) . . ?
C15 C20 C19 110.8(6) . . ?
C15 C20 C22 109.2(6) . . ?
C19 C20 C13 113.9(6) . . ?
C19 C20 C22 111.0(7) . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 N1 C8 C9 175.4(6) . . . . ?
O2 N1 C8 C21 -3.6(12) . . . . ?
O3 C9 C12 C11 -1.8(10) . . . . ?
O3 C9 C12 C13 177.7(7) . . . . ?
O3 C10 C11 C12 -0.4(11) . . . . ?
O4 C13 C20 C15 30.9(6) . . . . ?
O4 C13 C20 C19 148.9(6) . . . . ?
O4 C13 C20 C22 -84.3(7) . . . . ?
O4 C14 C15 C16 -160.9(8) . . . . ?
O4 C14 C15 C20 11.4(8) . . . . ?
O5 C14 C15 C16 16.8(15) . . . . ?
O5 C14 C15 C20 -170.9(8) . . . . ?
F1 C3 C4 C5 -177.9(9) . . . . ?
N1 O2 C7 O1 1.5(14) . . . . ?
N1 O2 C7 C6 -179.8(6) . . . . ?
N1 C8 C9 O3 158.1(8) . . . . ?
N1 C8 C9 C12 -28.3(15) . . . . ?
C1 C2 C3 F1 178.1(10) . . . . ?
C1 C2 C3 C4 -0.9(18) . . . . ?
C1 C6 C7 O1 -12.2(16) . . . . ?
C1 C6 C7 O2 169.2(8) . . . . ?
C2 C1 C6 C5 -0.4(15) . . . . ?
C2 C1 C6 C7 -178.3(9) . . . . ?
C2 C3 C4 C5 1.1(18) . . . . ?
C3 C4 C5 C6 -0.9(14) . . . . ?
C4 C5 C6 C1 0.6(14) . . . . ?
C4 C5 C6 C7 178.3(9) . . . . ?
C5 C6 C7 O1 170.0(11) . . . . ?
C5 C6 C7 O2 -8.6(13) . . . . ?
C6 C1 C2 C3 0.6(16) . . . . ?
C7 O2 N1 C8 175.7(8) . . . . ?
C8 C9 C12 C11 -175.7(10) . . . . ?
C8 C9 C12 C13 3.8(16) . . . . ?
C9 O3 C10 C11 -0.7(11) . . . . ?
C9 C12 C13 O4 -131.1(8) . . . . ?
C9 C12 C13 C20 109.1(10) . . . . ?
C10 O3 C9 C8 176.6(8) . . . . ?
C10 O3 C9 C12 1.6(10) . . . . ?
C10 C11 C12 C9 1.3(10) . . . . ?
C10 C11 C12 C13 -178.1(8) . . . . ?
C11 C12 C13 O4 48.3(10) . . . . ?
C11 C12 C13 C20 -71.6(11) . . . . ?
C12 C13 C20 C15 152.5(7) . . . . ?
C12 C13 C20 C19 -89.5(8) . . . . ?
C12 C13 C20 C22 37.2(10) . . . . ?
C13 O4 C14 O5 -168.4(7) . . . . ?
C13 O4 C14 C15 9.6(8) . . . . ?
C14 O4 C13 C12 -155.2(6) . . . . ?
C14 O4 C13 C20 -26.3(7) . . . . ?
C14 C15 C16 C17 168.6(8) . . . . ?
C14 C15 C16 C23 -7.6(14) . . . . ?
C14 C15 C20 C13 -25.9(7) . . . . ?
C14 C15 C20 C19 -146.2(7) . . . . ?
C14 C15 C20 C22 91.2(8) . . . . ?
C15 C16 C17 C18 6.3(13) . . . . ?
C16 C15 C20 C13 146.8(8) . . . . ?
C16 C15 C20 C19 26.5(11) . . . . ?
C16 C15 C20 C22 -96.1(9) . . . . ?
C16 C17 C18 C19 -33.9(13) . . . . ?
C17 C18 C19 C20 57.1(11) . . . . ?
C18 C19 C20 C13 -164.0(7) . . . . ?
C18 C19 C20 C15 -52.5(10) . . . . ?
C18 C19 C20 C22 69.0(9) . . . . ?
C20 C15 C16 C17 -2.6(13) . . . . ?
C20 C15 C16 C23 -178.8(7) . . . . ?
C21 C8 C9 O3 -22.9(12) . . . . ?
C21 C8 C9 C12 150.7(9) . . . . ?
C23 C16 C17 C18 -177.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gy_373
_database_code_depnum_ccdc_archive 'CCDC 1524889'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2013-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   12.0929(8)
_cell_length_b                   7.6383(6)
_cell_length_c                   16.1738(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.513(6)
_cell_angle_gamma                90.00
_cell_volume                     1491.16(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8240
_cell_measurement_theta_min      3.6560
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3900
_exptl_crystal_size_mid          0.2300
_exptl_crystal_size_min          0.2100
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6975
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.7435
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0478905000
_diffrn_orient_matrix_UB_12      0.0275619000
_diffrn_orient_matrix_UB_13      0.0196356000
_diffrn_orient_matrix_UB_21      0.0193260000
_diffrn_orient_matrix_UB_22      0.0876350000
_diffrn_orient_matrix_UB_23      -0.0002344000
_diffrn_orient_matrix_UB_31      -0.0280648000
_diffrn_orient_matrix_UB_32      0.0132519000
_diffrn_orient_matrix_UB_33      -0.0393184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2527
_reflns_number_total             5025
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5025
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0781
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0841P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1765
_refine_ls_wR_factor_ref         0.2357
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C23(H23), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C26(H26), C28(H28)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6416(3) 0.4115(7) 0.1499(3) 0.0930(16) Uani 1 1 d . . .
O2 O 0.4952(3) 0.4368(6) 0.0602(2) 0.0670(11) Uani 1 1 d . . .
O3 O 0.1684(4) 0.4277(6) -0.0952(3) 0.0793(13) Uani 1 1 d . . .
O4 O 0.1633(4) -0.0328(7) -0.0537(4) 0.1014(16) Uani 1 1 d . . .
H4 H 0.2249 -0.0380 -0.0722 0.152 Uiso 1 1 calc R . .
O5 O 0.1777(4) -0.6505(8) -0.4356(3) 0.1009(17) Uani 1 1 d . . .
O6 O -0.0069(3) -0.6482(7) -0.4475(2) 0.0767(13) Uani 1 1 d . . .
O7 O -0.3783(4) -0.7183(8) -0.4362(3) 0.0972(16) Uani 1 1 d . . .
O8 O -0.3256(5) -1.1766(10) -0.4416(5) 0.132(2) Uani 1 1 d . . .
H8 H -0.2841 -1.1719 -0.4798 0.198 Uiso 1 1 calc R . .
C1 C 0.5040(4) 0.6384(9) 0.1657(3) 0.0568(14) Uani 1 1 d . . .
C2 C 0.5521(4) 0.7634(9) 0.2126(3) 0.0616(15) Uani 1 1 d . . .
C3 C 0.4933(5) 0.9293(11) 0.2308(4) 0.085(2) Uani 1 1 d . . .
H3A H 0.5301 1.0251 0.2043 0.102 Uiso 1 1 calc R . .
H3B H 0.5005 0.9496 0.2901 0.102 Uiso 1 1 calc R . .
C4 C 0.3712(5) 0.9335(10) 0.2029(4) 0.0789(19) Uani 1 1 d . . .
H4A H 0.3468 1.0542 0.1976 0.095 Uiso 1 1 calc R . .
H4B H 0.3287 0.8776 0.2445 0.095 Uiso 1 1 calc R . .
C5 C 0.3492(5) 0.8393(9) 0.1195(4) 0.0681(17) Uani 1 1 d . . .
H5A H 0.2706 0.8433 0.1035 0.082 Uiso 1 1 calc R . .
H5B H 0.3885 0.8987 0.0772 0.082 Uiso 1 1 calc R . .
C6 C 0.3874(4) 0.6482(8) 0.1259(3) 0.0514(13) Uani 1 1 d . . .
C7 C 0.4071(4) 0.5662(8) 0.0419(3) 0.0544(14) Uani 1 1 d . . .
H7 H 0.4360 0.6569 0.0063 0.065 Uiso 1 1 calc R . .
C8 C 0.5561(5) 0.4893(9) 0.1290(4) 0.0659(16) Uani 1 1 d . . .
C9 C 0.3130(4) 0.4757(8) -0.0052(3) 0.0563(14) Uani 1 1 d . . .
C10 C 0.2746(5) 0.3005(10) 0.0028(4) 0.0717(18) Uani 1 1 d . . .
H10 H 0.3043 0.2172 0.0398 0.086 Uiso 1 1 calc R . .
C11 C 0.1878(5) 0.2763(8) -0.0523(4) 0.0637(15) Uani 1 1 d . . .
C12 C 0.2482(6) 0.5445(10) -0.0668(4) 0.0775(19) Uani 1 1 d . . .
H12 H 0.2561 0.6570 -0.0877 0.093 Uiso 1 1 calc R . .
C13 C 0.6720(5) 0.7509(11) 0.2491(5) 0.089(2) Uani 1 1 d . . .
H13A H 0.6721 0.7207 0.3067 0.133 Uiso 1 1 calc R . .
H13B H 0.7082 0.8617 0.2434 0.133 Uiso 1 1 calc R . .
H13C H 0.7107 0.6626 0.2201 0.133 Uiso 1 1 calc R . .
C14 C 0.3086(4) 0.5380(10) 0.1743(4) 0.0734(18) Uani 1 1 d . . .
H14A H 0.3374 0.4213 0.1806 0.110 Uiso 1 1 calc R . .
H14B H 0.2372 0.5342 0.1449 0.110 Uiso 1 1 calc R . .
H14C H 0.3016 0.5890 0.2280 0.110 Uiso 1 1 calc R . .
C15 C 0.1135(5) 0.1256(11) -0.0765(4) 0.0781(18) Uani 1 1 d . . .
H15 H 0.1015 0.1264 -0.1370 0.094 Uiso 1 1 calc R . .
C16 C 0.0038(6) 0.1418(14) -0.0408(5) 0.103(3) Uani 1 1 d . . .
H16A H -0.0435 0.0481 -0.0609 0.154 Uiso 1 1 calc R . .
H16B H -0.0292 0.2520 -0.0569 0.154 Uiso 1 1 calc R . .
H16C H 0.0129 0.1359 0.0185 0.154 Uiso 1 1 calc R . .
C17 C 0.0713(4) -0.4554(9) -0.3529(3) 0.0588(15) Uani 1 1 d . . .
C18 C 0.1343(5) -0.3214(10) -0.3273(4) 0.0648(16) Uani 1 1 d . . .
C19 C 0.0925(5) -0.1805(11) -0.2721(4) 0.087(2) Uani 1 1 d . . .
H19A H 0.0876 -0.0717 -0.3031 0.105 Uiso 1 1 calc R . .
H19B H 0.1463 -0.1637 -0.2258 0.105 Uiso 1 1 calc R . .
C20 C -0.0190(6) -0.2180(13) -0.2387(5) 0.105(3) Uani 1 1 d . . .
H20A H -0.0090 -0.2923 -0.1901 0.126 Uiso 1 1 calc R . .
H20B H -0.0522 -0.1091 -0.2219 0.126 Uiso 1 1 calc R . .
C21 C -0.0954(5) -0.3070(11) -0.3025(5) 0.090(2) Uani 1 1 d . . .
H21A H -0.1071 -0.2310 -0.3503 0.109 Uiso 1 1 calc R . .
H21B H -0.1666 -0.3268 -0.2796 0.109 Uiso 1 1 calc R . .
C22 C -0.0485(4) -0.4822(8) -0.3302(3) 0.0584(15) Uani 1 1 d . . .
C23 C -0.0967(5) -0.5430(9) -0.4159(3) 0.0647(16) Uani 1 1 d . . .
H23 H -0.1092 -0.4403 -0.4516 0.078 Uiso 1 1 calc R . .
C24 C 0.0927(5) -0.5883(10) -0.4128(4) 0.0718(18) Uani 1 1 d . . .
C25 C -0.1992(5) -0.6514(10) -0.4195(3) 0.0704(18) Uani 1 1 d . . .
C26 C -0.2125(5) -0.8336(9) -0.4157(4) 0.0695(17) Uani 1 1 d . . .
H26 H -0.1553 -0.9140 -0.4068 0.083 Uiso 1 1 calc R . .
C27 C -0.3216(5) -0.8747(11) -0.4267(4) 0.0744(18) Uani 1 1 d . . .
C28 C -0.3030(6) -0.5859(12) -0.4316(5) 0.092(2) Uani 1 1 d . . .
H28 H -0.3203 -0.4675 -0.4361 0.110 Uiso 1 1 calc R . .
C29 C 0.2519(5) -0.2882(12) -0.3530(5) 0.089(2) Uani 1 1 d . . .
H29A H 0.2768 -0.3875 -0.3832 0.134 Uiso 1 1 calc R . .
H29B H 0.3004 -0.2702 -0.3045 0.134 Uiso 1 1 calc R . .
H29C H 0.2525 -0.1860 -0.3876 0.134 Uiso 1 1 calc R . .
C30 C -0.0546(5) -0.6258(11) -0.2649(4) 0.082(2) Uani 1 1 d . . .
H30A H -0.0198 -0.7301 -0.2840 0.124 Uiso 1 1 calc R . .
H30B H -0.1308 -0.6501 -0.2558 0.124 Uiso 1 1 calc R . .
H30C H -0.0172 -0.5877 -0.2141 0.124 Uiso 1 1 calc R . .
C31 C -0.3895(6) -1.0300(12) -0.4421(6) 0.092(2) Uani 1 1 d . . .
H31 H -0.4253 -1.0186 -0.4979 0.111 Uiso 1 1 calc R . .
C32 C -0.4788(6) -1.0573(15) -0.3840(5) 0.128(4) Uani 1 1 d . . .
H32A H -0.4463 -1.0820 -0.3296 0.192 Uiso 1 1 calc R . .
H32B H -0.5245 -1.1540 -0.4027 0.192 Uiso 1 1 calc R . .
H32C H -0.5233 -0.9534 -0.3822 0.192 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
O1 C8 1.223(7) . ?
O2 C7 1.470(6) . ?
O2 C8 1.356(7) . ?
O3 C11 1.362(7) . ?
O3 C12 1.372(7) . ?
O4 H4 0.8200 . ?
O4 C15 1.391(9) . ?
O5 C24 1.210(7) . ?
O6 C23 1.468(7) . ?
O6 C24 1.375(7) . ?
O7 C27 1.381(9) . ?
O7 C28 1.360(8) . ?
O8 H8 0.8200 . ?
O8 C31 1.360(10) . ?
C1 C2 1.331(8) . ?
C1 C6 1.515(7) . ?
C1 C8 1.447(8) . ?
C2 C3 1.491(10) . ?
C2 C13 1.534(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.518(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.538(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.533(9) . ?
C6 C7 1.528(7) . ?
C6 C14 1.524(8) . ?
C7 H7 0.9800 . ?
C7 C9 1.499(7) . ?
C9 C10 1.425(9) . ?
C9 C12 1.337(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.348(8) . ?
C11 C15 1.498(9) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.485(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.327(8) . ?
C17 C22 1.530(7) . ?
C17 C24 1.438(9) . ?
C18 C19 1.505(10) . ?
C18 C29 1.527(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.511(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.505(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.531(10) . ?
C22 C23 1.542(7) . ?
C22 C30 1.528(9) . ?
C23 H23 0.9800 . ?
C23 C25 1.489(8) . ?
C25 C26 1.402(10) . ?
C25 C28 1.355(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.357(8) . ?
C27 C31 1.456(10) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31 0.9800 . ?
C31 C32 1.489(10) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
C8 O2 C7 108.5(4) . . ?
C11 O3 C12 106.6(4) . . ?
C15 O4 H4 109.5 . . ?
C24 O6 C23 108.9(5) . . ?
C28 O7 C27 108.1(5) . . ?
C31 O8 H8 109.5 . . ?
C2 C1 C6 124.7(5) . . ?
C2 C1 C8 127.8(5) . . ?
C8 C1 C6 106.4(5) . . ?
C1 C2 C3 121.6(5) . . ?
C1 C2 C13 123.0(6) . . ?
C3 C2 C13 115.3(6) . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C2 C3 C4 115.3(6) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.3(5) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.6(5) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C6 C5 110.2(5) . . ?
C1 C6 C7 99.5(4) . . ?
C1 C6 C14 110.4(5) . . ?
C7 C6 C5 113.2(4) . . ?
C14 C6 C5 111.4(5) . . ?
C14 C6 C7 111.5(5) . . ?
O2 C7 C6 104.3(4) . . ?
O2 C7 H7 108.3 . . ?
O2 C7 C9 108.1(4) . . ?
C6 C7 H7 108.3 . . ?
C9 C7 C6 119.1(4) . . ?
C9 C7 H7 108.3 . . ?
O1 C8 O2 119.4(6) . . ?
O1 C8 C1 130.6(6) . . ?
O2 C8 C1 110.0(5) . . ?
C10 C9 C7 128.9(5) . . ?
C12 C9 C7 126.1(6) . . ?
C12 C9 C10 105.0(5) . . ?
C9 C10 H10 125.9 . . ?
C11 C10 C9 108.3(6) . . ?
C11 C10 H10 125.9 . . ?
O3 C11 C15 116.0(5) . . ?
C10 C11 O3 108.9(5) . . ?
C10 C11 C15 135.1(6) . . ?
O3 C12 H12 124.4 . . ?
C9 C12 O3 111.2(6) . . ?
C9 C12 H12 124.4 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C11 110.9(5) . . ?
O4 C15 H15 107.8 . . ?
O4 C15 C16 110.6(7) . . ?
C11 C15 H15 107.8 . . ?
C16 C15 C11 111.7(7) . . ?
C16 C15 H15 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 124.2(6) . . ?
C18 C17 C24 129.2(5) . . ?
C24 C17 C22 106.2(5) . . ?
C17 C18 C19 122.0(5) . . ?
C17 C18 C29 124.7(6) . . ?
C19 C18 C29 113.3(6) . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C18 C19 C20 114.6(6) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 111.3(6) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C20 C21 C22 111.9(6) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C17 C22 C21 109.1(5) . . ?
C17 C22 C23 97.8(5) . . ?
C21 C22 C23 113.6(5) . . ?
C30 C22 C17 110.4(5) . . ?
C30 C22 C21 113.0(6) . . ?
C30 C22 C23 111.9(5) . . ?
O6 C23 C22 103.3(4) . . ?
O6 C23 H23 108.9 . . ?
O6 C23 C25 108.3(5) . . ?
C22 C23 H23 108.9 . . ?
C25 C23 C22 118.1(5) . . ?
C25 C23 H23 108.9 . . ?
O5 C24 O6 119.0(6) . . ?
O5 C24 C17 132.3(6) . . ?
O6 C24 C17 108.7(5) . . ?
C26 C25 C23 130.3(6) . . ?
C28 C25 C23 124.2(7) . . ?
C28 C25 C26 105.4(6) . . ?
C25 C26 H26 125.2 . . ?
C27 C26 C25 109.7(7) . . ?
C27 C26 H26 125.2 . . ?
O7 C27 C31 114.5(6) . . ?
C26 C27 O7 106.6(6) . . ?
C26 C27 C31 138.1(8) . . ?
O7 C28 H28 124.9 . . ?
C25 C28 O7 110.1(7) . . ?
C25 C28 H28 124.9 . . ?
C18 C29 H29A 109.5 . . ?
C18 C29 H29B 109.5 . . ?
C18 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
C22 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O8 C31 C27 110.8(6) . . ?
O8 C31 H31 107.3 . . ?
O8 C31 C32 108.4(9) . . ?
C27 C31 H31 107.3 . . ?
C27 C31 C32 115.4(7) . . ?
C32 C31 H31 107.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C7 C9 C10 34.7(8) . . . . ?
O2 C7 C9 C12 -143.4(6) . . . . ?
O3 C11 C15 O4 157.5(6) . . . . ?
O3 C11 C15 C16 -78.5(8) . . . . ?
O6 C23 C25 C26 27.6(9) . . . . ?
O6 C23 C25 C28 -149.2(6) . . . . ?
O7 C27 C31 O8 172.4(7) . . . . ?
O7 C27 C31 C32 -63.9(10) . . . . ?
C1 C2 C3 C4 8.5(10) . . . . ?
C1 C6 C7 O2 32.7(5) . . . . ?
C1 C6 C7 C9 153.3(5) . . . . ?
C2 C1 C6 C5 20.8(8) . . . . ?
C2 C1 C6 C7 139.9(6) . . . . ?
C2 C1 C6 C14 -102.8(7) . . . . ?
C2 C1 C8 O1 25.6(11) . . . . ?
C2 C1 C8 O2 -153.8(6) . . . . ?
C2 C3 C4 C5 -37.7(9) . . . . ?
C3 C4 C5 C6 58.8(8) . . . . ?
C4 C5 C6 C1 -49.0(6) . . . . ?
C4 C5 C6 C7 -159.4(5) . . . . ?
C4 C5 C6 C14 74.0(6) . . . . ?
C5 C6 C7 O2 149.6(4) . . . . ?
C5 C6 C7 C9 -89.8(6) . . . . ?
C6 C1 C2 C3 0.2(10) . . . . ?
C6 C1 C2 C13 -177.7(6) . . . . ?
C6 C1 C8 O1 -166.4(7) . . . . ?
C6 C1 C8 O2 14.3(6) . . . . ?
C6 C7 C9 C10 -83.9(8) . . . . ?
C6 C7 C9 C12 97.9(7) . . . . ?
C7 O2 C8 O1 -171.6(5) . . . . ?
C7 O2 C8 C1 7.9(6) . . . . ?
C7 C9 C10 C11 180.0(5) . . . . ?
C7 C9 C12 O3 -178.6(5) . . . . ?
C8 O2 C7 C6 -26.5(5) . . . . ?
C8 O2 C7 C9 -154.3(5) . . . . ?
C8 C1 C2 C3 166.2(6) . . . . ?
C8 C1 C2 C13 -11.7(10) . . . . ?
C8 C1 C6 C5 -147.8(5) . . . . ?
C8 C1 C6 C7 -28.7(6) . . . . ?
C8 C1 C6 C14 88.7(6) . . . . ?
C9 C10 C11 O3 -0.3(8) . . . . ?
C9 C10 C11 C15 178.3(7) . . . . ?
C10 C9 C12 O3 2.9(7) . . . . ?
C10 C11 C15 O4 -21.0(11) . . . . ?
C10 C11 C15 C16 102.9(9) . . . . ?
C11 O3 C12 C9 -3.1(7) . . . . ?
C12 O3 C11 C10 2.0(7) . . . . ?
C12 O3 C11 C15 -176.9(5) . . . . ?
C12 C9 C10 C11 -1.6(7) . . . . ?
C13 C2 C3 C4 -173.5(6) . . . . ?
C14 C6 C7 O2 -83.8(5) . . . . ?
C14 C6 C7 C9 36.8(7) . . . . ?
C17 C18 C19 C20 8.6(10) . . . . ?
C17 C22 C23 O6 36.6(6) . . . . ?
C17 C22 C23 C25 156.1(6) . . . . ?
C18 C17 C22 C21 20.3(8) . . . . ?
C18 C17 C22 C23 138.6(6) . . . . ?
C18 C17 C22 C30 -104.5(7) . . . . ?
C18 C17 C24 O5 27.3(13) . . . . ?
C18 C17 C24 O6 -152.8(6) . . . . ?
C18 C19 C20 C21 -38.1(10) . . . . ?
C19 C20 C21 C22 60.2(10) . . . . ?
C20 C21 C22 C17 -49.6(8) . . . . ?
C20 C21 C22 C23 -157.6(6) . . . . ?
C20 C21 C22 C30 73.6(7) . . . . ?
C21 C22 C23 O6 151.5(5) . . . . ?
C21 C22 C23 C25 -89.0(7) . . . . ?
C22 C17 C18 C19 0.2(10) . . . . ?
C22 C17 C18 C29 -176.7(6) . . . . ?
C22 C17 C24 O5 -159.9(8) . . . . ?
C22 C17 C24 O6 20.0(7) . . . . ?
C22 C23 C25 C26 -89.3(9) . . . . ?
C22 C23 C25 C28 93.9(8) . . . . ?
C23 O6 C24 O5 -174.9(6) . . . . ?
C23 O6 C24 C17 5.1(7) . . . . ?
C23 C25 C26 C27 -176.2(6) . . . . ?
C23 C25 C28 O7 176.8(5) . . . . ?
C24 O6 C23 C22 -27.7(7) . . . . ?
C24 O6 C23 C25 -153.8(5) . . . . ?
C24 C17 C18 C19 171.7(6) . . . . ?
C24 C17 C18 C29 -5.2(11) . . . . ?
C24 C17 C22 C21 -152.9(6) . . . . ?
C24 C17 C22 C23 -34.6(6) . . . . ?
C24 C17 C22 C30 82.3(6) . . . . ?
C25 C26 C27 O7 -1.1(7) . . . . ?
C25 C26 C27 C31 168.3(8) . . . . ?
C26 C25 C28 O7 -0.7(8) . . . . ?
C26 C27 C31 O8 3.7(13) . . . . ?
C26 C27 C31 C32 127.4(10) . . . . ?
C27 O7 C28 C25 0.1(8) . . . . ?
C28 O7 C27 C26 0.6(7) . . . . ?
C28 O7 C27 C31 -171.6(6) . . . . ?
C28 C25 C26 C27 1.1(8) . . . . ?
C29 C18 C19 C20 -174.2(6) . . . . ?
C30 C22 C23 O6 -79.2(6) . . . . ?
C30 C22 C23 C25 40.4(8) . . . . ?

####################################################################### 
# 
# 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_gy_468
_database_code_depnum_ccdc_archive 'CCDC 1524894'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2013-12-15
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H25 N O5'
_chemical_formula_sum            'C24 H25 N O5'
_chemical_formula_weight         407.45
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.2307(5)
_cell_length_b                   23.9115(14)
_cell_length_c                   11.3903(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.192(7)
_cell_angle_gamma                90.00
_cell_volume                     2141.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2009
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2240
_cell_measurement_theta_min      3.6330
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8238
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.6066
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   22.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -71.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   63.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   41.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000   90.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0254648000
_diffrn_orient_matrix_UB_12      -0.0214761000
_diffrn_orient_matrix_UB_13      -0.0446403000
_diffrn_orient_matrix_UB_21      -0.0164895000
_diffrn_orient_matrix_UB_22      -0.0179135000
_diffrn_orient_matrix_UB_23      0.0447709000
_diffrn_orient_matrix_UB_31      -0.0849909000
_diffrn_orient_matrix_UB_32      0.0098917000
_diffrn_orient_matrix_UB_33      -0.0157824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3806
_reflns_number_total             5888
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         5888
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1856
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H27A,H27B} of C27, H31 of C31, {H29A,H29B} of C29, {H28A,H28B} of C28, H7
  of C7, {H5A,H5B} of C5, {H4A,H4B} of C4, {H3A,H3B} of C3, H46 of C46, H45 of
  C45, H43 of C43, H42 of C42, H38 of C38, H36 of C36, H22 of C22, H21 of C21,
  H19 of C19, H18 of C18, H14 of C14, H12 of C12
 At 1.5 times of:
  {H33A,H33B,H33C} of C33, {H9A,H9B,H9C} of C9, {H48A,H48B,H48C} of C48,
  {H47A,H47B,H47C} of C47, {H34A,H34B,H34C} of C34, {H24A,H24B,H24C} of C24,
  {H23A,H23B,H23C} of C23, {H10A,H10B,H10C} of C10
2.a Ternary CH refined with riding coordinates:
 C31(H31), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C3(H3A,H3B), C4(H4A,H4B),
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C38(H38), C42(H42), C43(H43), C45(H45), C46(H46), C12(H12),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 1.4003(4) 0.65791(16) 0.9415(3) 0.0584(9) Uani 1 1 d . . .
O7 O 1.6713(4) 0.68407(19) 1.0165(4) 0.0765(12) Uani 1 1 d . . .
O8 O 1.0430(4) 0.53435(17) 0.8176(4) 0.0700(11) Uani 1 1 d . . .
O9 O 0.5639(4) 0.47046(15) 0.6862(3) 0.0559(9) Uani 1 1 d . . .
O10 O 0.6330(6) 0.4255(2) 0.5334(5) 0.1044(18) Uani 1 1 d . . .
N2 N 0.7350(5) 0.49215(19) 0.7203(4) 0.0559(11) Uani 1 1 d . . .
C25 C 1.4672(6) 0.6975(2) 1.1340(4) 0.0525(12) Uani 1 1 d . . .
C26 C 1.5347(7) 0.7356(2) 1.2209(5) 0.0633(14) Uani 1 1 d . . .
C27 C 1.4326(9) 0.7520(3) 1.3068(6) 0.091(2) Uani 1 1 d . . .
H27A H 1.4024 0.7911 1.2928 0.110 Uiso 1 1 calc R . .
H27B H 1.5065 0.7487 1.3904 0.110 Uiso 1 1 calc R . .
C28 C 1.2709(9) 0.7195(4) 1.2979(6) 0.094(2) Uani 1 1 d . . .
H28A H 1.1952 0.7421 1.3293 0.113 Uiso 1 1 calc R . .
H28B H 1.2985 0.6859 1.3478 0.113 Uiso 1 1 calc R . .
C29 C 1.1819(7) 0.7034(3) 1.1651(5) 0.0687(16) Uani 1 1 d . . .
H29A H 1.0794 0.6825 1.1608 0.082 Uiso 1 1 calc R . .
H29B H 1.1497 0.7369 1.1158 0.082 Uiso 1 1 calc R . .
C30 C 1.2998(6) 0.6682(2) 1.1151(4) 0.0512(12) Uani 1 1 d . . .
C31 C 1.2429(6) 0.6622(2) 0.9745(4) 0.0482(11) Uani 1 1 d . . .
H31 H 1.1852 0.6968 0.9389 0.058 Uiso 1 1 calc R . .
C32 C 1.5318(6) 0.6812(2) 1.0313(5) 0.0562(12) Uani 1 1 d . . .
C33 C 1.6995(7) 0.7645(3) 1.2361(6) 0.088(2) Uani 1 1 d . . .
H33A H 1.7368 0.7578 1.1651 0.133 Uiso 1 1 calc R . .
H33B H 1.7828 0.7503 1.3079 0.133 Uiso 1 1 calc R . .
H33C H 1.6853 0.8039 1.2452 0.133 Uiso 1 1 calc R . .
C34 C 1.3309(8) 0.6095(3) 1.1741(5) 0.0702(16) Uani 1 1 d . . .
H34A H 1.3933 0.6129 1.2595 0.105 Uiso 1 1 calc R . .
H34B H 1.3952 0.5874 1.1331 0.105 Uiso 1 1 calc R . .
H34C H 1.2237 0.5916 1.1662 0.105 Uiso 1 1 calc R . .
C35 C 1.1333(6) 0.6143(2) 0.9177(5) 0.0519(12) Uani 1 1 d . . .
C36 C 0.9568(6) 0.6069(2) 0.9068(4) 0.0511(12) Uani 1 1 d . . .
H36 H 0.8887 0.6308 0.9361 0.061 Uiso 1 1 calc R . .
C37 C 0.9088(5) 0.5586(2) 0.8459(4) 0.0489(11) Uani 1 1 d . . .
C38 C 1.1774(7) 0.5688(3) 0.8654(6) 0.0725(17) Uani 1 1 d . . .
H38 H 1.2871 0.5617 0.8622 0.087 Uiso 1 1 calc R . .
C39 C 0.7446(6) 0.5316(2) 0.7984(4) 0.0476(11) Uani 1 1 d . . .
C40 C 0.5335(7) 0.4344(2) 0.5895(5) 0.0615(14) Uani 1 1 d . . .
C41 C 0.3611(6) 0.4101(2) 0.5623(4) 0.0512(12) Uani 1 1 d . . .
C42 C 0.3202(7) 0.3677(2) 0.4760(5) 0.0640(14) Uani 1 1 d . . .
H42 H 0.3993 0.3559 0.4375 0.077 Uiso 1 1 calc R . .
C43 C 0.1607(7) 0.3426(3) 0.4468(5) 0.0663(15) Uani 1 1 d . . .
H43 H 0.1334 0.3147 0.3874 0.080 Uiso 1 1 calc R . .
C44 C 0.0417(6) 0.3585(2) 0.5046(5) 0.0608(14) Uani 1 1 d . . .
C45 C 0.0837(6) 0.4018(2) 0.5894(5) 0.0607(14) Uani 1 1 d . . .
H45 H 0.0037 0.4143 0.6264 0.073 Uiso 1 1 calc R . .
C46 C 0.2418(6) 0.4266(2) 0.6199(5) 0.0523(12) Uani 1 1 d . . .
H46 H 0.2688 0.4545 0.6794 0.063 Uiso 1 1 calc R . .
C47 C 0.6009(6) 0.5529(3) 0.8386(6) 0.0748(17) Uani 1 1 d . . .
H47A H 0.5730 0.5262 0.8926 0.112 Uiso 1 1 calc R . .
H47B H 0.5039 0.5586 0.7682 0.112 Uiso 1 1 calc R . .
H47C H 0.6324 0.5877 0.8813 0.112 Uiso 1 1 calc R . .
C48 C -0.1278(7) 0.3300(3) 0.4748(6) 0.085(2) Uani 1 1 d . . .
H48A H -0.2092 0.3507 0.4119 0.128 Uiso 1 1 calc R . .
H48B H -0.1646 0.3284 0.5472 0.128 Uiso 1 1 calc R . .
H48C H -0.1181 0.2928 0.4461 0.128 Uiso 1 1 calc R . .
O1 O 0.3591(4) 0.55138(17) 0.4596(3) 0.0655(10) Uani 1 1 d . . .
O2 O 0.1530(4) 0.57297(15) 0.5417(3) 0.0560(9) Uani 1 1 d . . .
O3 O -0.0995(4) 0.69806(15) 0.6604(4) 0.0668(10) Uani 1 1 d . . .
O4 O -0.4750(4) 0.77174(15) 0.7712(3) 0.0630(10) Uani 1 1 d . . .
O5 O -0.2908(6) 0.8366(2) 0.8763(5) 0.1109(19) Uani 1 1 d . . .
N1 N -0.3363(5) 0.74988(19) 0.7331(4) 0.0597(11) Uani 1 1 d . . .
C1 C 0.0596(6) 0.5317(2) 0.3511(4) 0.0501(11) Uani 1 1 d . . .
C2 C 0.0579(7) 0.4942(2) 0.2652(5) 0.0641(14) Uani 1 1 d . . .
C3 C -0.1093(9) 0.4727(3) 0.1849(6) 0.091(2) Uani 1 1 d . . .
H3A H -0.1151 0.4330 0.2003 0.109 Uiso 1 1 calc R . .
H3B H -0.1106 0.4770 0.1000 0.109 Uiso 1 1 calc R . .
C4 C -0.2713(9) 0.5003(4) 0.1998(6) 0.098(2) Uani 1 1 d . . .
H4A H -0.3003 0.5326 0.1462 0.117 Uiso 1 1 calc R . .
H4B H -0.3650 0.4740 0.1753 0.117 Uiso 1 1 calc R . .
C5 C -0.2469(7) 0.5184(3) 0.3314(5) 0.0747(17) Uani 1 1 d . . .
H5A H -0.2280 0.4858 0.3844 0.090 Uiso 1 1 calc R . .
H5B H -0.3488 0.5371 0.3373 0.090 Uiso 1 1 calc R . .
C6 C -0.0951(6) 0.5580(2) 0.3739(4) 0.0530(12) Uani 1 1 d . . .
C7 C -0.0305(5) 0.5665(2) 0.5135(4) 0.0486(11) Uani 1 1 d . . .
H7 H -0.0543 0.5326 0.5541 0.058 Uiso 1 1 calc R . .
C8 C 0.2081(6) 0.5515(2) 0.4498(4) 0.0524(12) Uani 1 1 d . . .
C9 C 0.2111(8) 0.4695(3) 0.2400(6) 0.0797(18) Uani 1 1 d . . .
H9A H 0.3119 0.4833 0.2992 0.120 Uiso 1 1 calc R . .
H9B H 0.2125 0.4799 0.1589 0.120 Uiso 1 1 calc R . .
H9C H 0.2072 0.4295 0.2458 0.120 Uiso 1 1 calc R . .
C10 C -0.1323(7) 0.6144(3) 0.3065(5) 0.0657(15) Uani 1 1 d . . .
H10A H -0.1572 0.6084 0.2196 0.099 Uiso 1 1 calc R . .
H10B H -0.0347 0.6383 0.3344 0.099 Uiso 1 1 calc R . .
H10C H -0.2282 0.6318 0.3234 0.099 Uiso 1 1 calc R . .
C11 C -0.0952(5) 0.6160(2) 0.5656(4) 0.0478(11) Uani 1 1 d . . .
C12 C -0.2632(6) 0.6260(2) 0.5712(4) 0.0513(12) Uani 1 1 d . . .
H12 H -0.3569 0.6027 0.5412 0.062 Uiso 1 1 calc R . .
C13 C -0.2609(5) 0.6753(2) 0.6279(4) 0.0483(11) Uani 1 1 d . . .
C14 C -0.0038(6) 0.6603(2) 0.6196(6) 0.0674(16) Uani 1 1 d . . .
H14 H 0.1114 0.6648 0.6282 0.081 Uiso 1 1 calc R . .
C15 C -0.3868(6) 0.7054(2) 0.6700(4) 0.0468(11) Uani 1 1 d . . .
C16 C -0.4269(8) 0.8146(2) 0.8525(5) 0.0663(15) Uani 1 1 d . . .
C17 C -0.5635(7) 0.8289(2) 0.9068(5) 0.0567(13) Uani 1 1 d . . .
C18 C -0.5250(8) 0.8661(3) 1.0051(6) 0.0734(16) Uani 1 1 d . . .
H18 H -0.4179 0.8825 1.0308 0.088 Uiso 1 1 calc R . .
C19 C -0.6430(8) 0.8790(3) 1.0649(5) 0.0725(16) Uani 1 1 d . . .
H19 H -0.6134 0.9031 1.1319 0.087 Uiso 1 1 calc R . .
C20 C -0.8040(8) 0.8566(3) 1.0269(5) 0.0685(15) Uani 1 1 d . . .
C21 C -0.8453(7) 0.8207(2) 0.9267(5) 0.0599(13) Uani 1 1 d . . .
H21 H -0.9545 0.8059 0.8983 0.072 Uiso 1 1 calc R . .
C22 C -0.7254(7) 0.8068(2) 0.8689(5) 0.0588(13) Uani 1 1 d . . .
H22 H -0.7543 0.7820 0.8030 0.071 Uiso 1 1 calc R . .
C23 C -0.5623(6) 0.6822(3) 0.6392(5) 0.0611(14) Uani 1 1 d . . .
H23A H -0.5679 0.6480 0.5942 0.092 Uiso 1 1 calc R . .
H23B H -0.6412 0.7087 0.5900 0.092 Uiso 1 1 calc R . .
H23C H -0.5910 0.6751 0.7136 0.092 Uiso 1 1 calc R . .
C24 C -0.9325(9) 0.8705(3) 1.0955(7) 0.094(2) Uani 1 1 d . . .
H24A H -0.9918 0.8371 1.1056 0.141 Uiso 1 1 calc R . .
H24B H -1.0126 0.8975 1.0494 0.141 Uiso 1 1 calc R . .
H24C H -0.8740 0.8857 1.1748 0.141 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
O6 C31 1.455(5) . ?
O6 C32 1.368(6) . ?
O7 C32 1.211(6) . ?
O8 C37 1.369(5) . ?
O8 C38 1.357(6) . ?
O9 N2 1.442(5) . ?
O9 C40 1.362(6) . ?
O10 C40 1.198(6) . ?
N2 C39 1.283(6) . ?
C25 C26 1.338(7) . ?
C25 C30 1.504(7) . ?
C25 C32 1.474(7) . ?
C26 C27 1.517(8) . ?
C26 C33 1.486(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.519(9) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.522(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.517(7) . ?
C30 C31 1.537(6) . ?
C30 C34 1.545(7) . ?
C31 H31 0.9800 . ?
C31 C35 1.485(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.431(7) . ?
C35 C38 1.340(8) . ?
C36 H36 0.9300 . ?
C36 C37 1.343(7) . ?
C37 C39 1.451(7) . ?
C38 H38 0.9300 . ?
C39 C47 1.480(7) . ?
C40 C41 1.480(7) . ?
C41 C42 1.382(7) . ?
C41 C46 1.391(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.391(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.385(7) . ?
C44 C45 1.389(8) . ?
C44 C48 1.499(7) . ?
C45 H45 0.9300 . ?
C45 C46 1.377(7) . ?
C46 H46 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
O1 C8 1.215(5) . ?
O2 C7 1.457(5) . ?
O2 C8 1.358(6) . ?
O3 C13 1.381(5) . ?
O3 C14 1.368(6) . ?
O4 N1 1.434(5) . ?
O4 C16 1.360(6) . ?
O5 C16 1.193(6) . ?
N1 C15 1.282(6) . ?
C1 C2 1.324(7) . ?
C1 C6 1.510(7) . ?
C1 C8 1.473(7) . ?
C2 C3 1.499(8) . ?
C2 C9 1.495(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.541(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.516(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.527(7) . ?
C6 C7 1.534(7) . ?
C6 C10 1.538(8) . ?
C7 H7 0.9800 . ?
C7 C11 1.491(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.423(6) . ?
C11 C14 1.339(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.341(7) . ?
C13 C15 1.455(6) . ?
C14 H14 0.9300 . ?
C15 C23 1.489(6) . ?
C16 C17 1.474(7) . ?
C17 C18 1.391(7) . ?
C17 C22 1.378(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(8) . ?
C20 C21 1.388(8) . ?
C20 C24 1.526(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(7) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C32 O6 C31 110.3(4) . . ?
C38 O8 C37 105.5(4) . . ?
C40 O9 N2 112.1(4) . . ?
C39 N2 O9 107.8(4) . . ?
C26 C25 C30 125.8(5) . . ?
C26 C25 C32 126.9(5) . . ?
C32 C25 C30 107.0(4) . . ?
C25 C26 C27 117.7(5) . . ?
C25 C26 C33 124.5(5) . . ?
C33 C26 C27 117.7(6) . . ?
C26 C27 H27A 107.9 . . ?
C26 C27 H27B 107.9 . . ?
C26 C27 C28 117.8(5) . . ?
H27A C27 H27B 107.2 . . ?
C28 C27 H27A 107.9 . . ?
C28 C27 H27B 107.9 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C27 C28 C29 110.5(5) . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
C28 C29 H29A 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C30 C29 C28 109.9(5) . . ?
C30 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
C25 C30 C29 110.3(4) . . ?
C25 C30 C31 100.1(4) . . ?
C25 C30 C34 109.6(4) . . ?
C29 C30 C31 114.3(4) . . ?
C29 C30 C34 112.6(4) . . ?
C31 C30 C34 109.2(4) . . ?
O6 C31 C30 104.8(3) . . ?
O6 C31 H31 108.3 . . ?
O6 C31 C35 107.8(4) . . ?
C30 C31 H31 108.3 . . ?
C35 C31 C30 119.0(4) . . ?
C35 C31 H31 108.3 . . ?
O6 C32 C25 108.0(4) . . ?
O7 C32 O6 119.5(5) . . ?
O7 C32 C25 132.4(5) . . ?
C26 C33 H33A 109.5 . . ?
C26 C33 H33B 109.5 . . ?
C26 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 109.5 . . ?
C30 C34 H34B 109.5 . . ?
C30 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C31 127.1(5) . . ?
C38 C35 C31 127.6(4) . . ?
C38 C35 C36 105.2(5) . . ?
C35 C36 H36 126.7 . . ?
C37 C36 C35 106.7(4) . . ?
C37 C36 H36 126.7 . . ?
O8 C37 C39 116.8(4) . . ?
C36 C37 O8 110.5(4) . . ?
C36 C37 C39 132.4(4) . . ?
O8 C38 H38 124.0 . . ?
C35 C38 O8 112.0(4) . . ?
C35 C38 H38 124.0 . . ?
N2 C39 C37 116.5(4) . . ?
N2 C39 C47 125.2(5) . . ?
C37 C39 C47 118.2(5) . . ?
O9 C40 C41 110.7(4) . . ?
O10 C40 O9 123.6(5) . . ?
O10 C40 C41 125.6(5) . . ?
C42 C41 C40 117.1(5) . . ?
C42 C41 C46 119.1(5) . . ?
C46 C41 C40 123.8(5) . . ?
C41 C42 H42 120.0 . . ?
C41 C42 C43 120.1(5) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 119.4 . . ?
C44 C43 C42 121.2(5) . . ?
C44 C43 H43 119.4 . . ?
C43 C44 C45 118.1(5) . . ?
C43 C44 C48 120.6(6) . . ?
C45 C44 C48 121.3(5) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 C44 121.2(5) . . ?
C46 C45 H45 119.4 . . ?
C41 C46 H46 119.8 . . ?
C45 C46 C41 120.4(5) . . ?
C45 C46 H46 119.8 . . ?
C39 C47 H47A 109.5 . . ?
C39 C47 H47B 109.5 . . ?
C39 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C8 O2 C7 110.5(4) . . ?
C14 O3 C13 104.7(4) . . ?
C16 O4 N1 112.6(4) . . ?
C15 N1 O4 108.5(4) . . ?
C2 C1 C6 125.7(5) . . ?
C2 C1 C8 127.4(5) . . ?
C8 C1 C6 106.7(4) . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 C9 125.7(5) . . ?
C9 C2 C3 115.0(5) . . ?
C2 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
C2 C3 C4 117.0(6) . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 H3A 108.0 . . ?
C4 C3 H3B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.4(5) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.3(5) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C1 C6 C5 109.9(5) . . ?
C1 C6 C7 100.5(3) . . ?
C1 C6 C10 109.4(4) . . ?
C5 C6 C7 114.3(4) . . ?
C5 C6 C10 111.2(4) . . ?
C7 C6 C10 111.0(4) . . ?
O2 C7 C6 105.2(3) . . ?
O2 C7 H7 108.8 . . ?
O2 C7 C11 107.3(4) . . ?
C6 C7 H7 108.8 . . ?
C11 C7 C6 117.5(4) . . ?
C11 C7 H7 108.8 . . ?
O1 C8 O2 119.7(4) . . ?
O1 C8 C1 131.7(5) . . ?
O2 C8 C1 108.6(4) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 128.1(4) . . ?
C14 C11 C7 126.3(4) . . ?
C14 C11 C12 105.6(4) . . ?
C11 C12 H12 126.5 . . ?
C13 C12 C11 107.1(4) . . ?
C13 C12 H12 126.5 . . ?
O3 C13 C15 116.0(4) . . ?
C12 C13 O3 110.6(4) . . ?
C12 C13 C15 133.2(4) . . ?
O3 C14 H14 123.9 . . ?
C11 C14 O3 112.1(4) . . ?
C11 C14 H14 123.9 . . ?
N1 C15 C13 116.8(4) . . ?
N1 C15 C23 124.9(4) . . ?
C13 C15 C23 118.3(5) . . ?
O4 C16 C17 110.8(5) . . ?
O5 C16 O4 123.4(5) . . ?
O5 C16 C17 125.8(5) . . ?
C18 C17 C16 117.7(5) . . ?
C22 C17 C16 124.5(5) . . ?
C22 C17 C18 117.8(5) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(6) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(6) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 118.6(5) . . ?
C19 C20 C24 120.3(6) . . ?
C21 C20 C24 121.1(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(6) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 121.3(5) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O6 C31 C35 C36 -167.9(5) . . . . ?
O6 C31 C35 C38 11.9(8) . . . . ?
O8 C37 C39 N2 -9.5(7) . . . . ?
O8 C37 C39 C47 173.3(5) . . . . ?
O9 N2 C39 C37 179.2(4) . . . . ?
O9 N2 C39 C47 -3.7(7) . . . . ?
O9 C40 C41 C42 -172.4(5) . . . . ?
O9 C40 C41 C46 6.3(7) . . . . ?
O10 C40 C41 C42 9.5(9) . . . . ?
O10 C40 C41 C46 -171.9(6) . . . . ?
N2 O9 C40 O10 -5.7(8) . . . . ?
N2 O9 C40 C41 176.2(4) . . . . ?
C25 C26 C27 C28 6.9(9) . . . . ?
C25 C30 C31 O6 30.1(5) . . . . ?
C25 C30 C31 C35 150.7(4) . . . . ?
C26 C25 C30 C29 25.4(7) . . . . ?
C26 C25 C30 C31 146.2(5) . . . . ?
C26 C25 C30 C34 -99.1(6) . . . . ?
C26 C25 C32 O6 -158.3(5) . . . . ?
C26 C25 C32 O7 23.0(10) . . . . ?
C26 C27 C28 C29 -35.6(9) . . . . ?
C27 C28 C29 C30 58.9(8) . . . . ?
C28 C29 C30 C25 -53.2(6) . . . . ?
C28 C29 C30 C31 -165.1(5) . . . . ?
C28 C29 C30 C34 69.6(6) . . . . ?
C29 C30 C31 O6 148.1(4) . . . . ?
C29 C30 C31 C35 -91.4(6) . . . . ?
C30 C25 C26 C27 -1.6(8) . . . . ?
C30 C25 C26 C33 -179.1(5) . . . . ?
C30 C25 C32 O6 15.5(6) . . . . ?
C30 C25 C32 O7 -163.2(6) . . . . ?
C30 C31 C35 C36 73.1(7) . . . . ?
C30 C31 C35 C38 -107.1(6) . . . . ?
C31 O6 C32 O7 -176.1(5) . . . . ?
C31 O6 C32 C25 5.0(6) . . . . ?
C31 C35 C36 C37 178.1(5) . . . . ?
C31 C35 C38 O8 -177.2(5) . . . . ?
C32 O6 C31 C30 -23.0(5) . . . . ?
C32 O6 C31 C35 -150.7(4) . . . . ?
C32 C25 C26 C27 171.1(6) . . . . ?
C32 C25 C26 C33 -6.4(9) . . . . ?
C32 C25 C30 C29 -148.5(4) . . . . ?
C32 C25 C30 C31 -27.7(5) . . . . ?
C32 C25 C30 C34 87.0(5) . . . . ?
C33 C26 C27 C28 -175.4(6) . . . . ?
C34 C30 C31 O6 -84.8(5) . . . . ?
C34 C30 C31 C35 35.7(6) . . . . ?
C35 C36 C37 O8 0.4(6) . . . . ?
C35 C36 C37 C39 -173.8(5) . . . . ?
C36 C35 C38 O8 2.6(7) . . . . ?
C36 C37 C39 N2 164.4(5) . . . . ?
C36 C37 C39 C47 -12.8(8) . . . . ?
C37 O8 C38 C35 -2.4(7) . . . . ?
C38 O8 C37 C36 1.2(6) . . . . ?
C38 O8 C37 C39 176.4(5) . . . . ?
C38 C35 C36 C37 -1.8(6) . . . . ?
C40 O9 N2 C39 170.4(4) . . . . ?
C40 C41 C42 C43 179.5(5) . . . . ?
C40 C41 C46 C45 -180.0(5) . . . . ?
C41 C42 C43 C44 -1.4(9) . . . . ?
C42 C41 C46 C45 -1.4(8) . . . . ?
C42 C43 C44 C45 2.4(9) . . . . ?
C42 C43 C44 C48 -178.2(6) . . . . ?
C43 C44 C45 C46 -3.0(8) . . . . ?
C44 C45 C46 C41 2.5(8) . . . . ?
C46 C41 C42 C43 0.8(8) . . . . ?
C48 C44 C45 C46 177.7(5) . . . . ?
O2 C7 C11 C12 -173.8(4) . . . . ?
O2 C7 C11 C14 4.8(7) . . . . ?
O3 C13 C15 N1 -0.1(6) . . . . ?
O3 C13 C15 C23 -179.1(4) . . . . ?
O4 N1 C15 C13 -177.0(4) . . . . ?
O4 N1 C15 C23 1.8(6) . . . . ?
O4 C16 C17 C18 170.5(5) . . . . ?
O4 C16 C17 C22 -7.7(8) . . . . ?
O5 C16 C17 C18 -8.6(9) . . . . ?
O5 C16 C17 C22 173.1(6) . . . . ?
N1 O4 C16 O5 9.7(8) . . . . ?
N1 O4 C16 C17 -169.4(4) . . . . ?
C1 C2 C3 C4 5.6(9) . . . . ?
C1 C6 C7 O2 28.0(5) . . . . ?
C1 C6 C7 C11 147.3(4) . . . . ?
C2 C1 C6 C5 26.8(7) . . . . ?
C2 C1 C6 C7 147.5(5) . . . . ?
C2 C1 C6 C10 -95.6(6) . . . . ?
C2 C1 C8 O1 22.1(10) . . . . ?
C2 C1 C8 O2 -157.9(5) . . . . ?
C2 C3 C4 C5 -32.9(10) . . . . ?
C3 C4 C5 C6 56.6(8) . . . . ?
C4 C5 C6 C1 -52.6(7) . . . . ?
C4 C5 C6 C7 -164.6(5) . . . . ?
C4 C5 C6 C10 68.7(7) . . . . ?
C5 C6 C7 O2 145.6(5) . . . . ?
C5 C6 C7 C11 -95.2(6) . . . . ?
C6 C1 C2 C3 -2.8(8) . . . . ?
C6 C1 C2 C9 177.9(5) . . . . ?
C6 C1 C8 O1 -163.8(6) . . . . ?
C6 C1 C8 O2 16.2(6) . . . . ?
C6 C7 C11 C12 68.1(6) . . . . ?
C6 C7 C11 C14 -113.3(6) . . . . ?
C7 O2 C8 O1 -177.3(4) . . . . ?
C7 O2 C8 C1 2.7(6) . . . . ?
C7 C11 C12 C13 178.8(5) . . . . ?
C7 C11 C14 O3 -178.5(5) . . . . ?
C8 O2 C7 C6 -20.2(5) . . . . ?
C8 O2 C7 C11 -146.1(4) . . . . ?
C8 C1 C2 C3 170.3(6) . . . . ?
C8 C1 C2 C9 -8.9(9) . . . . ?
C8 C1 C6 C5 -147.5(4) . . . . ?
C8 C1 C6 C7 -26.8(5) . . . . ?
C8 C1 C6 C10 90.1(5) . . . . ?
C9 C2 C3 C4 -175.1(6) . . . . ?
C10 C6 C7 O2 -87.6(5) . . . . ?
C10 C6 C7 C11 31.6(5) . . . . ?
C11 C12 C13 O3 -0.3(5) . . . . ?
C11 C12 C13 C15 -173.7(5) . . . . ?
C12 C11 C14 O3 0.4(6) . . . . ?
C12 C13 C15 N1 173.0(5) . . . . ?
C12 C13 C15 C23 -5.9(8) . . . . ?
C13 O3 C14 C11 -0.6(6) . . . . ?
C14 O3 C13 C12 0.5(6) . . . . ?
C14 O3 C13 C15 175.2(4) . . . . ?
C14 C11 C12 C13 -0.1(6) . . . . ?
C16 O4 N1 C15 171.6(4) . . . . ?
C16 C17 C18 C19 -176.4(6) . . . . ?
C16 C17 C22 C21 177.9(5) . . . . ?
C17 C18 C19 C20 -1.8(10) . . . . ?
C18 C17 C22 C21 -0.4(8) . . . . ?
C18 C19 C20 C21 0.0(9) . . . . ?
C18 C19 C20 C24 178.9(6) . . . . ?
C19 C20 C21 C22 1.6(8) . . . . ?
C20 C21 C22 C17 -1.4(8) . . . . ?
C22 C17 C18 C19 2.0(9) . . . . ?
C24 C20 C21 C22 -177.3(6) . . . . ?

