# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_mun1923
_database_code_depnum_ccdc_archive 'CCDC 1949991'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 N2 O, C H4 O'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40

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

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

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

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

_cell_length_a                   12.6038(2)
_cell_length_b                   8.2717(2)
_cell_length_c                   18.3638(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.1087(12)
_cell_angle_gamma                90
_cell_volume                     1809.02(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      73.85

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12501
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.751
_diffrn_reflns_theta_max         74.138
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3591
_reflns_number_gt                3231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+0.6757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3591
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47587(8) 0.69800(14) 0.30451(6) 0.0314(3) Uani 1 1 d . . . . .
H1O H 0.4535(19) 0.722(3) 0.2479(14) 0.055(6) Uiso 1 1 d . . . . .
N1 N 0.14121(10) 0.36887(14) 0.46148(7) 0.0242(3) Uani 1 1 d . . . . .
H1N H 0.1932(17) 0.416(2) 0.5040(12) 0.037(5) Uiso 1 1 d . . . . .
N2 N 0.05833(10) 0.27932(14) 0.34200(7) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.14372(12) 0.36426(17) 0.38796(8) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.04792(11) 0.28325(16) 0.46268(8) 0.0234(3) Uani 1 1 d . . . . .
C3 C -0.00239(11) 0.22833(16) 0.38853(8) 0.0235(3) Uani 1 1 d . . . . .
C4 C -0.10343(12) 0.13331(16) 0.36864(8) 0.0248(3) Uani 1 1 d . . . . .
C5 C -0.15863(13) 0.07444(18) 0.29461(9) 0.0298(3) Uani 1 1 d . . . . .
H5 H -0.129017 0.095964 0.254219 0.036 Uiso 1 1 calc R U . . .
C6 C -0.25681(13) -0.01561(19) 0.27963(9) 0.0340(3) Uani 1 1 d . . . . .
H6 H -0.293561 -0.055145 0.229053 0.041 Uiso 1 1 calc R U . . .
C7 C -0.30128(13) -0.04802(19) 0.33745(10) 0.0340(4) Uani 1 1 d . . . . .
H7 H -0.368427 -0.109441 0.326166 0.041 Uiso 1 1 calc R U . . .
C8 C -0.24866(12) 0.00852(18) 0.41268(9) 0.0294(3) Uani 1 1 d . . . . .
C9 C -0.29548(13) -0.0197(2) 0.47290(10) 0.0357(4) Uani 1 1 d . . . . .
H9 H -0.362115 -0.082081 0.462234 0.043 Uiso 1 1 calc R U . . .
C10 C -0.24705(13) 0.0405(2) 0.54441(10) 0.0348(4) Uani 1 1 d . . . . .
H10 H -0.281019 0.021254 0.582779 0.042 Uiso 1 1 calc R U . . .
C11 C -0.14477(12) 0.13331(18) 0.56376(9) 0.0288(3) Uani 1 1 d . . . . .
C12 C -0.09332(14) 0.19528(19) 0.63784(9) 0.0322(3) Uani 1 1 d . . . . .
H12 H -0.126313 0.176002 0.676722 0.039 Uiso 1 1 calc R U . . .
C13 C 0.00483(14) 0.28417(19) 0.65542(9) 0.0322(3) Uani 1 1 d . . . . .
H13 H 0.038624 0.324525 0.706202 0.039 Uiso 1 1 calc R U . . .
C14 C 0.05444(12) 0.31499(18) 0.59955(8) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.121832 0.376175 0.612197 0.033 Uiso 1 1 calc R U . . .
C15 C 0.00516(11) 0.25591(16) 0.52464(8) 0.0240(3) Uani 1 1 d . . . . .
C16 C -0.09558(12) 0.16291(17) 0.50564(8) 0.0246(3) Uani 1 1 d . . . . .
C17 C -0.14791(11) 0.10098(16) 0.42922(8) 0.0248(3) Uani 1 1 d . . . . .
C18 C 0.22959(12) 0.44883(17) 0.36463(8) 0.0255(3) Uani 1 1 d . . . . .
C19 C 0.32860(13) 0.5027(2) 0.41994(9) 0.0348(4) Uani 1 1 d . . . . .
H19 H 0.341178 0.480059 0.472830 0.042 Uiso 1 1 calc R U . . .
C20 C 0.40854(13) 0.5882(2) 0.39912(9) 0.0371(4) Uani 1 1 d . . . . .
H20 H 0.474576 0.625439 0.437645 0.045 Uiso 1 1 calc R U . . .
C21 C 0.39226(12) 0.61975(18) 0.32183(8) 0.0272(3) Uani 1 1 d . . . . .
C22 C 0.29339(12) 0.57002(17) 0.26618(8) 0.0273(3) Uani 1 1 d . . . . .
H22 H 0.280870 0.593493 0.213386 0.033 Uiso 1 1 calc R U . . .
C23 C 0.21276(12) 0.48594(17) 0.28768(8) 0.0275(3) Uani 1 1 d . . . . .
H23 H 0.145161 0.453328 0.249285 0.033 Uiso 1 1 calc R U . . .
O1S O 0.67778(10) 0.53918(16) 0.39919(7) 0.0393(3) Uani 1 1 d . . . . .
H1OS H 0.624(3) 0.614(4) 0.3656(18) 0.092(10) Uiso 1 1 d . . . . .
C1S C 0.63810(18) 0.3799(2) 0.37808(13) 0.0512(5) Uani 1 1 d . . . . .
H1SA H 0.652921 0.314680 0.423577 0.061 Uiso 1 1 calc R U . . .
H1SB H 0.675780 0.334410 0.345113 0.061 Uiso 1 1 calc R U . . .
H1SC H 0.558712 0.382631 0.351243 0.061 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.3602(17) . ?
N1 C1 1.3615(18) . ?
N1 C2 1.3788(17) . ?
N2 C1 1.3302(18) . ?
N2 C3 1.3864(18) . ?
C1 C18 1.4655(19) . ?
C2 C3 1.3773(19) . ?
C2 C15 1.4276(19) . ?
C3 C4 1.4382(19) . ?
C4 C5 1.396(2) . ?
C4 C17 1.425(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.403(2) . ?
C8 C17 1.4273(19) . ?
C8 C9 1.433(2) . ?
C9 C10 1.349(3) . ?
C10 C11 1.442(2) . ?
C11 C12 1.399(2) . ?
C11 C16 1.420(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.399(2) . ?
C15 C16 1.4267(19) . ?
C16 C17 1.436(2) . ?
C18 C23 1.393(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.384(2) . ?
C20 C21 1.391(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.391(2) . ?
O1S C1S 1.418(2) . ?

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
C1 N1 C2 107.35(12) . . ?
C1 N2 C3 105.36(12) . . ?
N2 C1 N1 111.55(12) . . ?
N2 C1 C18 126.03(13) . . ?
N1 C1 C18 122.39(13) . . ?
C3 C2 N1 105.83(12) . . ?
C3 C2 C15 124.33(13) . . ?
N1 C2 C15 129.82(13) . . ?
C2 C3 N2 109.91(12) . . ?
C2 C3 C4 120.95(13) . . ?
N2 C3 C4 129.14(13) . . ?
C5 C4 C17 119.77(13) . . ?
C5 C4 C3 123.75(14) . . ?
C17 C4 C3 116.49(13) . . ?
C6 C5 C4 120.41(15) . . ?
C7 C6 C5 120.70(15) . . ?
C6 C7 C8 120.87(14) . . ?
C7 C8 C17 119.28(14) . . ?
C7 C8 C9 121.64(14) . . ?
C17 C8 C9 119.05(14) . . ?
C10 C9 C8 121.46(14) . . ?
C9 C10 C11 121.30(15) . . ?
C12 C11 C16 119.36(14) . . ?
C12 C11 C10 121.83(14) . . ?
C16 C11 C10 118.81(14) . . ?
C13 C12 C11 121.07(14) . . ?
C12 C13 C14 120.64(14) . . ?
C13 C14 C15 120.00(14) . . ?
C14 C15 C16 120.12(13) . . ?
C14 C15 C2 124.50(13) . . ?
C16 C15 C2 115.37(13) . . ?
C11 C16 C15 118.80(13) . . ?
C11 C16 C17 119.95(13) . . ?
C15 C16 C17 121.24(13) . . ?
C4 C17 C8 118.96(13) . . ?
C4 C17 C16 121.59(13) . . ?
C8 C17 C16 119.42(13) . . ?
C23 C18 C19 118.03(13) . . ?
C23 C18 C1 121.33(13) . . ?
C19 C18 C1 120.55(13) . . ?
C20 C19 C18 121.29(14) . . ?
C19 C20 C21 120.03(14) . . ?
O1 C21 C22 123.06(13) . . ?
O1 C21 C20 117.47(13) . . ?
C22 C21 C20 119.47(13) . . ?
C21 C22 C23 120.11(13) . . ?
C22 C23 C18 121.02(13) . . ?

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
C3 N2 C1 N1 0.56(15) . . . . ?
C3 N2 C1 C18 -177.54(13) . . . . ?
C2 N1 C1 N2 -0.69(16) . . . . ?
C2 N1 C1 C18 177.49(12) . . . . ?
C1 N1 C2 C3 0.51(15) . . . . ?
C1 N1 C2 C15 -177.78(14) . . . . ?
N1 C2 C3 N2 -0.19(15) . . . . ?
C15 C2 C3 N2 178.23(12) . . . . ?
N1 C2 C3 C4 -179.94(12) . . . . ?
C15 C2 C3 C4 -1.5(2) . . . . ?
C1 N2 C3 C2 -0.22(15) . . . . ?
C1 N2 C3 C4 179.51(14) . . . . ?
C2 C3 C4 C5 179.82(13) . . . . ?
N2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C17 0.40(19) . . . . ?
N2 C3 C4 C17 -179.30(13) . . . . ?
C17 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C6 -179.40(13) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C17 0.1(2) . . . . ?
C6 C7 C8 C9 178.03(15) . . . . ?
C7 C8 C9 C10 -177.29(15) . . . . ?
C17 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 -179.52(15) . . . . ?
C9 C10 C11 C16 0.8(2) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C10 C11 C12 C13 -179.99(14) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C13 C14 C15 C2 178.72(14) . . . . ?
C3 C2 C15 C14 -178.29(13) . . . . ?
N1 C2 C15 C14 -0.3(2) . . . . ?
C3 C2 C15 C16 1.0(2) . . . . ?
N1 C2 C15 C16 178.97(13) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C10 C11 C16 C15 179.50(13) . . . . ?
C12 C11 C16 C17 -179.58(13) . . . . ?
C10 C11 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C2 C15 C16 C11 -178.68(12) . . . . ?
C14 C15 C16 C17 179.96(12) . . . . ?
C2 C15 C16 C17 0.68(19) . . . . ?
C5 C4 C17 C8 0.0(2) . . . . ?
C3 C4 C17 C8 179.41(12) . . . . ?
C5 C4 C17 C16 -178.26(13) . . . . ?
C3 C4 C17 C16 1.19(19) . . . . ?
C7 C8 C17 C4 0.0(2) . . . . ?
C9 C8 C17 C4 -178.00(13) . . . . ?
C7 C8 C17 C16 178.24(13) . . . . ?
C9 C8 C17 C16 0.3(2) . . . . ?
C11 C16 C17 C4 177.59(13) . . . . ?
C15 C16 C17 C4 -1.8(2) . . . . ?
C11 C16 C17 C8 -0.6(2) . . . . ?
C15 C16 C17 C8 -179.98(12) . . . . ?
N2 C1 C18 C23 18.3(2) . . . . ?
N1 C1 C18 C23 -159.64(14) . . . . ?
N2 C1 C18 C19 -165.37(15) . . . . ?
N1 C1 C18 C19 16.7(2) . . . . ?
C23 C18 C19 C20 -1.0(2) . . . . ?
C1 C18 C19 C20 -177.44(15) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C19 C20 C21 O1 -177.13(15) . . . . ?
C19 C20 C21 C22 2.4(3) . . . . ?
O1 C21 C22 C23 177.95(13) . . . . ?
C20 C21 C22 C23 -1.6(2) . . . . ?
C21 C22 C23 C18 -0.6(2) . . . . ?
C19 C18 C23 C22 1.8(2) . . . . ?
C1 C18 C23 C22 178.28(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N2 1.00(2) 1.68(2) 2.6678(15) 168(2) 2 yes
N1 H1N O1S 0.92(2) 2.01(2) 2.9169(17) 165.3(18) 3_666 yes
O1S H1OS O1 0.97(3) 1.96(3) 2.8859(16) 157(3) . yes

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_mun1928
_database_code_depnum_ccdc_archive 'CCDC 1972837'
loop_
_audit_author_name
_audit_author_address
'Dr. Jian-Bin Lin'
;Memorial University
Canada
;
_audit_update_record             
;
2019-12-18 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H54 N2 O'
_chemical_formula_sum            'C43 H54 N2 O'
_chemical_formula_weight         614.88

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

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

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

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

_cell_length_a                   9.4376(3)
_cell_length_b                   11.2292(4)
_cell_length_c                   17.0583(6)
_cell_angle_alpha                90.117(2)
_cell_angle_beta                 93.940(2)
_cell_angle_gamma                101.967(2)
_cell_volume                     1764.07(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      73.91

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.634
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.516
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3492
_exptl_absorpt_correction_T_max  0.9488
_exptl_absorpt_process_details   'SADABS (version 2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60985
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         74.366
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             6879
_reflns_number_gt                5586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (version 2014/5)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1028P)²+0.2975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6879
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08813(11) 0.23654(10) 0.68976(7) 0.0376(3) Uani 1 1 d . . . . .
N1 N 0.32886(12) 0.67170(11) 0.45731(7) 0.0288(3) Uani 1 1 d . . . . .
N2 N 0.51002(12) 0.71625(11) 0.55205(7) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.38237(14) 0.63779(13) 0.52562(8) 0.0286(3) Uani 1 1 d . . . . .
C2 C 0.42452(14) 0.77561(12) 0.43874(8) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.53776(14) 0.80596(12) 0.49602(8) 0.0272(3) Uani 1 1 d . . . . .
C11 C 0.31156(15) 0.53106(13) 0.56864(8) 0.0292(3) Uani 1 1 d . . . . .
C12 C 0.15925(15) 0.50623(14) 0.57104(9) 0.0326(3) Uani 1 1 d . . . . .
H12 H 0.104886 0.558872 0.545216 0.039 Uiso 1 1 calc R U . . .
C13 C 0.08790(15) 0.40676(14) 0.61025(9) 0.0353(3) Uani 1 1 d . . . . .
H13 H -0.014827 0.391207 0.611139 0.042 Uiso 1 1 calc R U . . .
C14 C 0.16663(15) 0.32879(13) 0.64870(8) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.31630(15) 0.34892(13) 0.64424(8) 0.0317(3) Uani 1 1 d . . . . .
H15 H 0.370226 0.294637 0.668502 0.038 Uiso 1 1 calc R U . . .
C16 C 0.38625(15) 0.44910(13) 0.60400(8) 0.0313(3) Uani 1 1 d . . . . .
H16 H 0.488336 0.461811 0.600624 0.038 Uiso 1 1 calc R U . . .
C21 C 0.16468(16) 0.15676(14) 0.73258(9) 0.0358(3) Uani 1 1 d . . . . .
H21A H 0.246428 0.204292 0.766418 0.043 Uiso 1 1 calc R U . . .
H21B H 0.203714 0.105128 0.695987 0.043 Uiso 1 1 calc R U . . .
C22 C 0.05545(17) 0.07909(15) 0.78205(9) 0.0374(3) Uani 1 1 d . . . . .
H22A H -0.024590 0.032516 0.746694 0.045 Uiso 1 1 calc R U . . .
H22B H 0.013586 0.133318 0.815414 0.045 Uiso 1 1 calc R U . . .
C23 C 0.11726(18) -0.00993(15) 0.83468(10) 0.0404(4) Uani 1 1 d . . . . .
H23A H 0.202301 0.035000 0.867431 0.048 Uiso 1 1 calc R U . . .
H23B H 0.150611 -0.069809 0.801607 0.048 Uiso 1 1 calc R U . . .
C24 C 0.00461(18) -0.07696(14) 0.88781(9) 0.0386(3) Uani 1 1 d . . . . .
H24A H -0.029262 -0.016148 0.919850 0.046 Uiso 1 1 calc R U . . .
H24B H -0.080015 -0.121183 0.854457 0.046 Uiso 1 1 calc R U . . .
C25 C 0.05855(19) -0.16723(16) 0.94275(10) 0.0422(4) Uani 1 1 d . . . . .
H25A H 0.096544 -0.226280 0.911276 0.051 Uiso 1 1 calc R U . . .
H25B H 0.139580 -0.122877 0.978429 0.051 Uiso 1 1 calc R U . . .
C26 C -0.05988(19) -0.23616(15) 0.99156(9) 0.0404(4) Uani 1 1 d . . . . .
H26A H -0.139587 -0.281363 0.955429 0.049 Uiso 1 1 calc R U . . .
H26B H -0.099655 -0.176286 1.021327 0.049 Uiso 1 1 calc R U . . .
C27 C -0.0118(2) -0.32558(16) 1.04929(10) 0.0428(4) Uani 1 1 d . . . . .
H27A H 0.062950 -0.280176 1.088075 0.051 Uiso 1 1 calc R U . . .
H27B H 0.033352 -0.382919 1.020387 0.051 Uiso 1 1 calc R U . . .
C28 C -0.1363(2) -0.39788(16) 1.09283(10) 0.0438(4) Uani 1 1 d . . . . .
H28A H -0.184922 -0.340061 1.118927 0.053 Uiso 1 1 calc R U . . .
H28B H -0.208304 -0.446417 1.054008 0.053 Uiso 1 1 calc R U . . .
C29 C -0.0910(2) -0.48267(19) 1.15391(11) 0.0549(5) Uani 1 1 d . . . . .
H29A H -0.026700 -0.433694 1.195735 0.066 Uiso 1 1 calc R U . . .
H29B H -0.034463 -0.535661 1.129070 0.066 Uiso 1 1 calc R U . . .
C30 C -0.2189(3) -0.5622(2) 1.19100(12) 0.0677(6) Uani 1 1 d . . . . .
H30A H -0.183181 -0.616499 1.228910 0.102 Uiso 1 1 calc R U . . .
H30B H -0.283294 -0.610898 1.149948 0.102 Uiso 1 1 calc R U . . .
H30C H -0.272690 -0.510504 1.218017 0.102 Uiso 1 1 calc R U . . .
C31 C 0.59469(15) 0.70977(13) 0.62656(8) 0.0298(3) Uani 1 1 d . . . . .
H31A H 0.533405 0.656448 0.662705 0.036 Uiso 1 1 calc R U . . .
H31B H 0.622415 0.792119 0.650974 0.036 Uiso 1 1 calc R U . . .
C32 C 0.73230(15) 0.66065(14) 0.61623(8) 0.0329(3) Uani 1 1 d . . . . .
H32A H 0.704961 0.571524 0.606894 0.040 Uiso 1 1 calc R U . . .
H32B H 0.778816 0.697717 0.569325 0.040 Uiso 1 1 calc R U . . .
C33 C 0.84177(17) 0.68733(16) 0.68775(10) 0.0411(4) Uani 1 1 d . . . . .
H33A H 0.885944 0.775410 0.689134 0.049 Uiso 1 1 calc R U . . .
H33B H 0.920366 0.642824 0.680727 0.049 Uiso 1 1 calc R U . . .
C34 C 0.7796(2) 0.65309(16) 0.76728(10) 0.0454(4) Uani 1 1 d . . . . .
H34A H 0.860135 0.671165 0.808707 0.055 Uiso 1 1 calc R U . . .
H34B H 0.710832 0.706007 0.777586 0.055 Uiso 1 1 calc R U . . .
C35 C 0.7021(2) 0.52196(16) 0.77480(10) 0.0453(4) Uani 1 1 d . . . . .
H35A H 0.765176 0.468011 0.757672 0.054 Uiso 1 1 calc R U . . .
H35B H 0.612425 0.506473 0.739326 0.054 Uiso 1 1 calc R U . . .
C36 C 0.6623(2) 0.49024(18) 0.85831(10) 0.0499(4) Uani 1 1 d . . . . .
H36A H 0.752716 0.502021 0.893040 0.060 Uiso 1 1 calc R U . . .
H36B H 0.604271 0.547773 0.876280 0.060 Uiso 1 1 calc R U . . .
C37 C 0.5785(2) 0.36328(18) 0.86744(11) 0.0545(5) Uani 1 1 d . . . . .
H37A H 0.629471 0.306447 0.842148 0.065 Uiso 1 1 calc R U . . .
H37B H 0.481933 0.355359 0.838904 0.065 Uiso 1 1 calc R U . . .
C38 C 0.5567(2) 0.32451(18) 0.95173(11) 0.0530(4) Uani 1 1 d . . . . .
H38A H 0.653043 0.332038 0.980424 0.064 Uiso 1 1 calc R U . . .
H38B H 0.505365 0.380964 0.977171 0.064 Uiso 1 1 calc R U . . .
C39 C 0.4730(3) 0.1978(2) 0.95930(13) 0.0731(7) Uani 1 1 d . . . . .
H39A H 0.521244 0.142130 0.930907 0.088 Uiso 1 1 calc R U . . .
H39B H 0.374806 0.191872 0.933144 0.088 Uiso 1 1 calc R U . . .
C40 C 0.4575(3) 0.1548(2) 1.04290(14) 0.0762(7) Uani 1 1 d . . . . .
H40A H 0.400070 0.071346 1.042448 0.114 Uiso 1 1 calc R U . . .
H40B H 0.408396 0.208368 1.071527 0.114 Uiso 1 1 calc R U . . .
H40C H 0.553874 0.156779 1.068850 0.114 Uiso 1 1 calc R U . . .
C41 C 0.41707(15) 0.84581(13) 0.36920(8) 0.0293(3) Uani 1 1 d . . . . .
C42 C 0.30704(16) 0.81431(15) 0.30914(9) 0.0351(3) Uani 1 1 d . . . . .
H42 H 0.232640 0.743813 0.313593 0.042 Uiso 1 1 calc R U . . .
C43 C 0.30649(18) 0.88617(16) 0.24285(9) 0.0409(4) Uani 1 1 d . . . . .
H43 H 0.232445 0.863355 0.201776 0.049 Uiso 1 1 calc R U . . .
C44 C 0.41184(18) 0.98998(16) 0.23594(10) 0.0423(4) Uani 1 1 d . . . . .
H44 H 0.408744 1.038414 0.190511 0.051 Uiso 1 1 calc R U . . .
C45 C 0.52370(17) 1.02511(14) 0.29515(9) 0.0360(3) Uani 1 1 d . . . . .
C46 C 0.52800(15) 0.95143(13) 0.36288(8) 0.0298(3) Uani 1 1 d . . . . .
C47 C 0.64305(15) 0.98539(13) 0.42380(8) 0.0295(3) Uani 1 1 d . . . . .
C48 C 0.65239(14) 0.91267(13) 0.49220(8) 0.0287(3) Uani 1 1 d . . . . .
C49 C 0.76761(16) 0.95177(14) 0.54864(9) 0.0346(3) Uani 1 1 d . . . . .
H49 H 0.775791 0.904540 0.594234 0.042 Uiso 1 1 calc R U . . .
C50 C 0.87031(16) 1.05813(14) 0.53952(10) 0.0389(3) Uani 1 1 d . . . . .
H50 H 0.947172 1.082549 0.578904 0.047 Uiso 1 1 calc R U . . .
C51 C 0.86190(16) 1.12851(14) 0.47402(10) 0.0381(3) Uani 1 1 d . . . . .
H51 H 0.932599 1.201169 0.468568 0.046 Uiso 1 1 calc R U . . .
C52 C 0.74965(16) 1.09333(14) 0.41554(9) 0.0350(3) Uani 1 1 d . . . . .
C53 C 0.74000(18) 1.16635(15) 0.34679(10) 0.0407(4) Uani 1 1 d . . . . .
H53 H 0.810419 1.239284 0.341708 0.049 Uiso 1 1 calc R U . . .
C54 C 0.63300(18) 1.13327(15) 0.28949(10) 0.0411(4) Uani 1 1 d . . . . .
H54 H 0.630262 1.182773 0.244543 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.3669(17) . ?
O1 C21 1.4341(17) . ?
N1 C1 1.3261(18) . ?
N1 C2 1.3715(18) . ?
N2 C1 1.3836(18) . ?
N2 C3 1.3877(17) . ?
N2 C31 1.4643(16) . ?
C1 C11 1.4698(19) . ?
C2 C3 1.3846(19) . ?
C2 C41 1.4315(18) . ?
C3 C48 1.443(2) . ?
C11 C16 1.3859(19) . ?
C11 C12 1.4098(19) . ?
C12 C13 1.379(2) . ?
C13 C14 1.398(2) . ?
C14 C15 1.3909(19) . ?
C15 C16 1.389(2) . ?
C21 C22 1.5116(19) . ?
C22 C23 1.523(2) . ?
C23 C24 1.524(2) . ?
C24 C25 1.522(2) . ?
C25 C26 1.521(2) . ?
C26 C27 1.522(2) . ?
C27 C28 1.523(2) . ?
C28 C29 1.512(2) . ?
C29 C30 1.522(3) . ?
C31 C32 1.5330(19) . ?
C32 C33 1.530(2) . ?
C33 C34 1.533(2) . ?
C34 C35 1.512(2) . ?
C35 C36 1.522(2) . ?
C36 C37 1.494(3) . ?
C37 C38 1.518(2) . ?
C38 C39 1.487(3) . ?
C39 C40 1.514(3) . ?
C41 C42 1.397(2) . ?
C41 C46 1.420(2) . ?
C42 C43 1.391(2) . ?
C43 C44 1.377(3) . ?
C44 C45 1.403(2) . ?
C45 C46 1.4256(19) . ?
C45 C54 1.429(2) . ?
C46 C47 1.441(2) . ?
C47 C52 1.420(2) . ?
C47 C48 1.4337(19) . ?
C48 C49 1.399(2) . ?
C49 C50 1.390(2) . ?
C50 C51 1.377(2) . ?
C51 C52 1.397(2) . ?
C52 C53 1.441(2) . ?
C53 C54 1.349(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C21 118.23(11) . . ?
C1 N1 C2 105.07(11) . . ?
C1 N2 C3 106.47(11) . . ?
C1 N2 C31 126.73(11) . . ?
C3 N2 C31 126.72(12) . . ?
N1 C1 N2 112.00(12) . . ?
N1 C1 C11 123.58(13) . . ?
N2 C1 C11 124.40(12) . . ?
N1 C2 C3 111.34(12) . . ?
N1 C2 C41 126.84(13) . . ?
C3 C2 C41 121.80(13) . . ?
C2 C3 N2 105.12(12) . . ?
C2 C3 C48 123.01(13) . . ?
N2 C3 C48 131.86(13) . . ?
C16 C11 C12 117.68(13) . . ?
C16 C11 C1 123.26(12) . . ?
C12 C11 C1 118.98(12) . . ?
C13 C12 C11 121.07(13) . . ?
C12 C13 C14 120.04(13) . . ?
O1 C14 C15 124.18(13) . . ?
O1 C14 C13 116.12(12) . . ?
C15 C14 C13 119.70(13) . . ?
C16 C15 C14 119.42(13) . . ?
C11 C16 C15 121.96(13) . . ?
O1 C21 C22 106.20(12) . . ?
C21 C22 C23 114.45(13) . . ?
C22 C23 C24 111.47(13) . . ?
C25 C24 C23 114.64(14) . . ?
C26 C25 C24 112.57(14) . . ?
C25 C26 C27 115.12(15) . . ?
C26 C27 C28 112.94(15) . . ?
C29 C28 C27 114.33(16) . . ?
C28 C29 C30 113.15(18) . . ?
N2 C31 C32 112.60(11) . . ?
C33 C32 C31 112.66(12) . . ?
C32 C33 C34 115.37(13) . . ?
C35 C34 C33 115.81(15) . . ?
C34 C35 C36 112.81(15) . . ?
C37 C36 C35 114.49(16) . . ?
C36 C37 C38 115.03(17) . . ?
C39 C38 C37 114.02(18) . . ?
C38 C39 C40 114.9(2) . . ?
C42 C41 C46 120.13(13) . . ?
C42 C41 C2 122.85(14) . . ?
C46 C41 C2 117.02(13) . . ?
C43 C42 C41 119.99(15) . . ?
C44 C43 C42 120.89(15) . . ?
C43 C44 C45 120.86(14) . . ?
C44 C45 C46 119.17(15) . . ?
C44 C45 C54 121.68(14) . . ?
C46 C45 C54 119.15(15) . . ?
C41 C46 C45 118.95(14) . . ?
C41 C46 C47 121.15(13) . . ?
C45 C46 C47 119.90(14) . . ?
C52 C47 C48 119.43(14) . . ?
C52 C47 C46 119.01(13) . . ?
C48 C47 C46 121.56(13) . . ?
C49 C48 C47 118.08(13) . . ?
C49 C48 C3 126.52(13) . . ?
C47 C48 C3 115.39(13) . . ?
C50 C49 C48 121.50(15) . . ?
C51 C50 C49 120.73(15) . . ?
C50 C51 C52 120.17(15) . . ?
C51 C52 C47 120.09(14) . . ?
C51 C52 C53 120.57(15) . . ?
C47 C52 C53 119.35(15) . . ?
C54 C53 C52 121.36(15) . . ?
C53 C54 C45 121.22(15) . . ?

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
C2 N1 C1 N2 -0.11(15) . . . . ?
C2 N1 C1 C11 178.43(12) . . . . ?
C3 N2 C1 N1 0.18(15) . . . . ?
C31 N2 C1 N1 177.05(12) . . . . ?
C3 N2 C1 C11 -178.34(12) . . . . ?
C31 N2 C1 C11 -1.5(2) . . . . ?
C1 N1 C2 C3 -0.01(15) . . . . ?
C1 N1 C2 C41 178.21(13) . . . . ?
N1 C2 C3 N2 0.12(15) . . . . ?
C41 C2 C3 N2 -178.20(12) . . . . ?
N1 C2 C3 C48 -178.67(12) . . . . ?
C41 C2 C3 C48 3.0(2) . . . . ?
C1 N2 C3 C2 -0.17(14) . . . . ?
C31 N2 C3 C2 -177.04(12) . . . . ?
C1 N2 C3 C48 178.46(14) . . . . ?
C31 N2 C3 C48 1.6(2) . . . . ?
N1 C1 C11 C16 136.53(15) . . . . ?
N2 C1 C11 C16 -45.1(2) . . . . ?
N1 C1 C11 C12 -40.1(2) . . . . ?
N2 C1 C11 C12 138.31(14) . . . . ?
C16 C11 C12 C13 2.8(2) . . . . ?
C1 C11 C12 C13 179.61(14) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C21 O1 C14 C15 1.5(2) . . . . ?
C21 O1 C14 C13 -177.76(13) . . . . ?
C12 C13 C14 O1 176.43(14) . . . . ?
C12 C13 C14 C15 -2.9(2) . . . . ?
O1 C14 C15 C16 -176.84(13) . . . . ?
C13 C14 C15 C16 2.4(2) . . . . ?
C12 C11 C16 C15 -3.3(2) . . . . ?
C1 C11 C16 C15 -179.95(13) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C14 O1 C21 C22 170.78(13) . . . . ?
O1 C21 C22 C23 -178.02(13) . . . . ?
C21 C22 C23 C24 175.03(14) . . . . ?
C22 C23 C24 C25 -179.60(14) . . . . ?
C23 C24 C25 C26 -177.16(14) . . . . ?
C24 C25 C26 C27 -178.48(14) . . . . ?
C25 C26 C27 C28 -176.33(14) . . . . ?
C26 C27 C28 C29 -176.81(16) . . . . ?
C27 C28 C29 C30 -174.61(17) . . . . ?
C1 N2 C31 C32 104.29(15) . . . . ?
C3 N2 C31 C32 -79.46(16) . . . . ?
N2 C31 C32 C33 163.50(12) . . . . ?
C31 C32 C33 C34 49.70(19) . . . . ?
C32 C33 C34 C35 55.9(2) . . . . ?
C33 C34 C35 C36 171.84(15) . . . . ?
C34 C35 C36 C37 176.89(17) . . . . ?
C35 C36 C37 C38 171.65(17) . . . . ?
C36 C37 C38 C39 -180.0(2) . . . . ?
C37 C38 C39 C40 176.6(2) . . . . ?
N1 C2 C41 C42 -0.7(2) . . . . ?
C3 C2 C41 C42 177.39(13) . . . . ?
N1 C2 C41 C46 179.35(12) . . . . ?
C3 C2 C41 C46 -2.6(2) . . . . ?
C46 C41 C42 C43 0.3(2) . . . . ?
C2 C41 C42 C43 -179.69(13) . . . . ?
C41 C42 C43 C44 -1.2(2) . . . . ?
C42 C43 C44 C45 0.9(3) . . . . ?
C43 C44 C45 C46 0.4(2) . . . . ?
C43 C44 C45 C54 -179.24(15) . . . . ?
C42 C41 C46 C45 0.9(2) . . . . ?
C2 C41 C46 C45 -179.06(12) . . . . ?
C42 C41 C46 C47 -179.63(12) . . . . ?
C2 C41 C46 C47 0.37(19) . . . . ?
C44 C45 C46 C41 -1.3(2) . . . . ?
C54 C45 C46 C41 178.37(12) . . . . ?
C44 C45 C46 C47 179.27(13) . . . . ?
C54 C45 C46 C47 -1.1(2) . . . . ?
C41 C46 C47 C52 -178.61(12) . . . . ?
C45 C46 C47 C52 0.82(19) . . . . ?
C41 C46 C47 C48 1.56(19) . . . . ?
C45 C46 C47 C48 -179.01(12) . . . . ?
C52 C47 C48 C49 0.06(19) . . . . ?
C46 C47 C48 C49 179.89(12) . . . . ?
C52 C47 C48 C3 178.92(11) . . . . ?
C46 C47 C48 C3 -1.25(18) . . . . ?
C2 C3 C48 C49 177.76(13) . . . . ?
N2 C3 C48 C49 -0.7(2) . . . . ?
C2 C3 C48 C47 -0.99(19) . . . . ?
N2 C3 C48 C47 -179.42(13) . . . . ?
C47 C48 C49 C50 0.3(2) . . . . ?
C3 C48 C49 C50 -178.43(13) . . . . ?
C48 C49 C50 C51 -0.2(2) . . . . ?
C49 C50 C51 C52 -0.2(2) . . . . ?
C50 C51 C52 C47 0.6(2) . . . . ?
C50 C51 C52 C53 -179.97(14) . . . . ?
C48 C47 C52 C51 -0.5(2) . . . . ?
C46 C47 C52 C51 179.69(12) . . . . ?
C48 C47 C52 C53 -179.95(12) . . . . ?
C46 C47 C52 C53 0.2(2) . . . . ?
C51 C52 C53 C54 179.49(14) . . . . ?
C47 C52 C53 C54 -1.1(2) . . . . ?
C52 C53 C54 C45 0.8(2) . . . . ?
C44 C45 C54 C53 179.91(15) . . . . ?
C46 C45 C54 C53 0.3(2) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.052

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

data_za58-2-2
_database_code_depnum_ccdc_archive 'CCDC 1972848'
loop_
_audit_author_name
_audit_author_address
'Dr. Jian-Bin Lin'
;Memorial University
Canada
;
_audit_update_record             
;
2019-12-18 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2019-09-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H34 N2 O, 2(H2 O)'
_chemical_formula_sum            'C33 H38 N2 O3'
_chemical_formula_weight         510.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H34 N2 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9659(3)
_cell_length_b                   8.9998(3)
_cell_length_c                   19.2836(7)
_cell_angle_alpha                87.414(3)
_cell_angle_beta                 79.965(3)
_cell_angle_gamma                63.475(3)
_cell_volume                     1369.99(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0500
_cell_measurement_theta_min      5.4890
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.555
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00 118.00   0.50    2.00    --   47.20  75.00 -55.00  178
  2  ω     86.00 169.00   0.50   10.00    --  107.75  75.00 -55.00  166
  3  ω    151.00 176.00   0.50   10.00    --  107.75  45.00 -90.00   50
  4  ω    135.00 162.00   0.50   10.00    --  107.75 125.00-120.00   54
  5  ω     98.00 125.00   0.50   10.00    --  107.75  30.00 -90.00   54
  6  ω     96.00 178.00   0.50   10.00    --  107.75  45.00-120.00  164
  7  ω     97.00 129.00   0.50   10.00    --  107.75 125.00-120.00   64
  8  ω     97.00 133.00   0.50   10.00    --  107.75 125.00 -90.00   72
  9  ω     91.00 178.00   0.50   10.00    --  107.75  61.00 -30.00  174
 10  ω     95.00 146.00   0.50   10.00    --  107.75  45.00 -90.00  102
 11  ω     92.00 160.00   0.50   10.00    --  107.75  61.00-150.00  136
 12  ω     62.00 107.00   0.50   10.00    --  107.75-102.00 -88.30   90
 13  ω     82.00 109.00   0.50   10.00    --  107.75-125.00 -30.00   54
 14  ω     74.00 105.00   0.50   10.00    --  107.75 -94.00   0.00   62
 15  ω     65.00  96.00   0.50   10.00    --  107.75 -94.00 -30.00   62
 16  ω     52.00 108.00   0.50   10.00    --  107.75-125.00 -90.00  112
 17  ω     72.00 104.00   0.50   10.00    --  107.75 -94.00-180.00   64
 18  ω     37.00 106.00   0.50   10.00    --  107.75 -94.00 -60.00  138
 19  ω     42.00  69.00   0.50   10.00    --  107.75 -94.00   0.00   54
 20  ω     46.00  79.00   0.50   10.00    --  107.75 -61.00  60.00   66
 21  ω     76.00 106.00   0.50   10.00    --  107.75 -94.00 120.00   60
 22  ω     80.00 109.00   0.50   10.00    --  107.75-117.00 102.25   58
 23  ω     83.00 110.00   0.50   10.00    --  107.75-125.00 150.00   54
 24  ω     71.00  98.00   0.50   10.00    --  107.75-125.00 120.00   54
 25  ω     61.00  87.00   0.50   10.00    --  107.75 -75.00 176.00   52
 26  ω     45.00  71.00   0.50   10.00    --  107.75-125.00 150.00   52
 27  ω     41.00  70.00   0.50   10.00    --  107.75-117.00 102.25   58
 28  ω     40.00 105.00   0.50   10.00    --  107.75-125.00  90.00  130
 29  ω     35.00  62.00   0.50   10.00    --  107.75-125.00 120.00   54
 30  ω     39.00  69.00   0.50   10.00    --  107.75 -94.00 120.00   60
 31  ω     36.00 100.00   0.50   10.00    --  107.75 -94.00 150.00  128
 32  ω     37.00  63.00   0.50   10.00    --  107.75 -61.00   0.00   52
 33  ω     41.00  69.00   0.50   10.00    --  107.75 -61.00 -30.00   56
 34  ω     40.00  65.00   0.50   10.00    --  107.75 -61.00 -90.00   50
 35  ω     37.00  64.00   0.50   10.00    --  107.75-125.00 -30.00   54
 36  ω    -16.00  27.00   0.50    2.00    --   47.20 -19.00  60.00   86
 37  ω     12.00  58.00   0.50    2.00    --   47.20 -75.00 176.00   92
 38  ω     -2.00  23.00   0.50    2.00    --  -47.20  19.00 -60.00   50
 39  ω    -15.00  22.00   0.50    2.00    --  -47.20  19.00-120.00   74
 40  ω    -30.00  26.00   0.50    2.00    --  -47.20  37.00 -90.00  112
 41  ω    -42.00 -15.00   0.50   10.00    --  -86.25  45.00-120.00   54
 42  ω    -68.00  -8.00   0.50    2.00    --  -47.20  75.00 -55.00  120
 43  ω    -74.00 -47.00   0.50   10.00    --  -86.25  75.00 -55.00   54
 44  ω    -43.00 -14.00   0.50   10.00    --  -86.25  45.00  90.00   58
 45  ω    -43.00 -18.00   0.50   10.00    --  -86.25  45.00 120.00   50
 46  ω   -119.00 -32.00   0.50    2.00    --  -47.20 -75.00 176.00  174
 47  ω    140.00 167.00   0.50   10.00    --  107.75 125.00 150.00   54
 48  ω    135.00 160.00   0.50   10.00    --  107.75  77.00 150.00   50
 49  ω    106.00 136.00   0.50   10.00    --  107.75 125.00 150.00   60
 50  ω     91.00 118.00   0.50   10.00    --  107.75  77.00 150.00   54
 51  ω     35.00  60.00   0.50   10.00    --  107.75 -61.00-180.00   50
 52  ω   -118.00 -74.00   0.50    2.00    --  -47.20-125.00 -90.00   88
 53  ω   -131.00-106.00   0.50   10.00    --  -86.25 -75.00 176.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0672291000
_diffrn_orient_matrix_UB_12      -0.1726522000
_diffrn_orient_matrix_UB_13      0.0323266000
_diffrn_orient_matrix_UB_21      0.0538495000
_diffrn_orient_matrix_UB_22      0.0664487000
_diffrn_orient_matrix_UB_23      0.0585301000
_diffrn_orient_matrix_UB_31      -0.1748971000
_diffrn_orient_matrix_UB_32      0.0492695000
_diffrn_orient_matrix_UB_33      0.0460492000
_diffrn_oxdiff_digest_frames     
;
01fa90c89af967b14fd43487be4a223f7200027f15a
;
_diffrn_oxdiff_digest_hkl        
;
016fa1f34f2c55f557aab61554c0ba00e572e8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5220
_reflns_number_total             5677
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.058
_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)+(0.0772P)²+0.5058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1371
_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 Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.53321(12) 0.13968(12) 0.59707(5) 0.0268(2) Uani 1 1 d . . . . .
N1 N -0.00914(14) 0.40862(14) 0.38166(6) 0.0228(2) Uani 1 1 d . . . . .
H1 H -0.031(2) 0.330(2) 0.4005(10) 0.032(4) Uiso 1 1 d . . . . .
N2 N 0.12091(14) 0.57108(14) 0.35728(6) 0.0231(2) Uani 1 1 d . . . . .
C1 C -0.07697(16) 0.50610(16) 0.32779(7) 0.0229(3) Uani 1 1 d . . . . .
C2 C -0.20724(16) 0.51326(17) 0.29210(7) 0.0239(3) Uani 1 1 d . . . . .
C3 C -0.29536(18) 0.41831(19) 0.30907(8) 0.0299(3) Uani 1 1 d . . . . .
H3 H -0.268947 0.341499 0.345754 0.036 Uiso 1 1 calc R . . . .
C4 C -0.4224(2) 0.4369(2) 0.27184(8) 0.0350(3) Uani 1 1 d . . . . .
H4 H -0.483117 0.373147 0.283803 0.042 Uiso 1 1 calc R . . . .
C5 C -0.46112(18) 0.5465(2) 0.21789(8) 0.0322(3) Uani 1 1 d . . . . .
H5 H -0.548134 0.557055 0.193249 0.039 Uiso 1 1 calc R . . . .
C6 C -0.37411(17) 0.64256(18) 0.19887(7) 0.0277(3) Uani 1 1 d . . . . .
C7 C -0.24566(16) 0.62787(17) 0.23696(7) 0.0243(3) Uani 1 1 d . . . . .
C8 C -0.41050(18) 0.75556(19) 0.14240(8) 0.0306(3) Uani 1 1 d . . . . .
H8 H -0.495092 0.764791 0.116548 0.037 Uiso 1 1 calc R . . . .
C9 C -0.32768(19) 0.84911(19) 0.12505(8) 0.0311(3) Uani 1 1 d . . . . .
H9 H -0.353933 0.921588 0.086885 0.037 Uiso 1 1 calc R . . . .
C10 C -0.20011(18) 0.84110(18) 0.16335(7) 0.0280(3) Uani 1 1 d . . . . .
C11 C -0.15886(17) 0.72917(17) 0.21917(7) 0.0244(3) Uani 1 1 d . . . . .
C12 C -0.1178(2) 0.9415(2) 0.14707(8) 0.0342(3) Uani 1 1 d . . . . .
H12 H -0.144757 1.015718 0.109515 0.041 Uiso 1 1 calc R . . . .
C13 C 0.0030(2) 0.9338(2) 0.18529(9) 0.0365(3) Uani 1 1 d . . . . .
H13 H 0.056920 1.003890 0.173935 0.044 Uiso 1 1 calc R . . . .
C14 C 0.04604(19) 0.82501(19) 0.23982(8) 0.0300(3) Uani 1 1 d . . . . .
H14 H 0.129693 0.820481 0.265192 0.036 Uiso 1 1 calc R . . . .
C15 C -0.03317(17) 0.72194(17) 0.25763(7) 0.0243(3) Uani 1 1 d . . . . .
C16 C 0.00476(16) 0.60498(16) 0.31271(7) 0.0224(3) Uani 1 1 d . . . . .
C17 C 0.10966(16) 0.45144(16) 0.39769(7) 0.0222(3) Uani 1 1 d . . . . .
C18 C 0.21504(16) 0.36907(16) 0.45089(7) 0.0227(3) Uani 1 1 d . . . . .
C19 C 0.35380(17) 0.39912(17) 0.45546(7) 0.0246(3) Uani 1 1 d . . . . .
H19 H 0.377103 0.474245 0.424544 0.029 Uiso 1 1 calc R . . . .
C20 C 0.45676(17) 0.32048(17) 0.50448(8) 0.0265(3) Uani 1 1 d . . . . .
H20 H 0.550001 0.342282 0.507160 0.032 Uiso 1 1 calc R . . . .
C21 C 0.42495(16) 0.20950(16) 0.55000(7) 0.0235(3) Uani 1 1 d . . . . .
C22 C 0.28896(16) 0.17629(17) 0.54589(7) 0.0244(3) Uani 1 1 d . . . . .
H22 H 0.267299 0.099547 0.576315 0.029 Uiso 1 1 calc R . . . .
C23 C 0.18545(16) 0.25707(17) 0.49663(7) 0.0241(3) Uani 1 1 d . . . . .
H23 H 0.092111 0.235317 0.494106 0.029 Uiso 1 1 calc R . . . .
C24 C 0.51115(17) 0.01863(17) 0.64383(7) 0.0243(3) Uani 1 1 d . . . . .
H24A H 0.527684 -0.079712 0.616534 0.029 Uiso 1 1 calc R . . . .
H24B H 0.395876 0.067019 0.672231 0.029 Uiso 1 1 calc R . . . .
C25 C 0.64274(17) -0.03025(17) 0.69122(7) 0.0254(3) Uani 1 1 d . . . . .
H25A H 0.625885 0.070316 0.716934 0.031 Uiso 1 1 calc R . . . .
H25B H 0.756701 -0.076222 0.661706 0.031 Uiso 1 1 calc R . . . .
C26 C 0.63490(17) -0.15840(17) 0.74444(7) 0.0254(3) Uani 1 1 d . . . . .
H26A H 0.516148 -0.122270 0.767894 0.030 Uiso 1 1 calc R . . . .
H26B H 0.673534 -0.266222 0.719314 0.030 Uiso 1 1 calc R . . . .
C27 C 0.74454(17) -0.18141(17) 0.80011(7) 0.0265(3) Uani 1 1 d . . . . .
H27A H 0.712252 -0.071255 0.821784 0.032 Uiso 1 1 calc R . . . .
H27B H 0.864143 -0.225676 0.776541 0.032 Uiso 1 1 calc R . . . .
C28 C 0.73109(19) -0.29745(19) 0.85854(8) 0.0310(3) Uani 1 1 d . . . . .
H28A H 0.793822 -0.413750 0.839793 0.037 Uiso 1 1 calc R . . . .
H28B H 0.610806 -0.273219 0.873280 0.037 Uiso 1 1 calc R . . . .
C29 C 0.8016(2) -0.2797(2) 0.92323(8) 0.0339(3) Uani 1 1 d . . . . .
H29A H 0.744576 -0.161443 0.939404 0.041 Uiso 1 1 calc R . . . .
H29B H 0.772712 -0.343993 0.961683 0.041 Uiso 1 1 calc R . . . .
C30 C 0.99247(19) -0.33802(19) 0.91061(8) 0.0321(3) Uani 1 1 d . . . . .
H30A H 1.025098 -0.291185 0.866430 0.039 Uiso 1 1 calc R . . . .
H30B H 1.050407 -0.460607 0.904275 0.039 Uiso 1 1 calc R . . . .
C31 C 1.0533(2) -0.2876(2) 0.97054(8) 0.0339(3) Uani 1 1 d . . . . .
H31A H 1.020230 -0.334097 1.014741 0.041 Uiso 1 1 calc R . . . .
H31B H 0.995487 -0.164963 0.976778 0.041 Uiso 1 1 calc R . . . .
C32 C 1.2441(2) -0.3461(2) 0.95823(9) 0.0358(3) Uani 1 1 d . . . . .
H32A H 1.301705 -0.469080 0.955223 0.043 Uiso 1 1 calc R . . . .
H32B H 1.278191 -0.305987 0.912399 0.043 Uiso 1 1 calc R . . . .
C33 C 1.3039(2) -0.2865(2) 1.01541(10) 0.0470(4) Uani 1 1 d . . . . .
H33A H 1.426676 -0.326076 1.003739 0.071 Uiso 1 1 calc GR . . . .
H33B H 1.275709 -0.330130 1.060662 0.071 Uiso 1 1 calc GR . . . .
H33C H 1.247768 -0.164729 1.018740 0.071 Uiso 1 1 calc GR . . . .
O1W O -0.09702(13) 0.15297(13) 0.43368(6) 0.0293(2) Uani 1 1 d . . . . .
H1WA H -0.125(3) 0.164(3) 0.4810(13) 0.055(6) Uiso 1 1 d . . . . .
H1WB H -0.021(3) 0.048(3) 0.4228(13) 0.065(7) Uiso 1 1 d . . . . .
O2W O 0.16249(13) -0.17616(13) 0.41736(5) 0.0274(2) Uani 1 1 d . . . . .
H2WA H 0.164(3) -0.262(3) 0.3940(12) 0.060(7) Uiso 1 1 d . . . . .
H2WB H 0.262(3) -0.181(3) 0.4020(11) 0.049(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.3682(16) . ?
O1 C24 1.4424(16) . ?
N1 C1 1.3711(17) . ?
N1 C17 1.3677(16) . ?
N2 C16 1.3859(16) . ?
N2 C17 1.3307(17) . ?
C1 C2 1.4322(18) . ?
C1 C16 1.3778(18) . ?
C2 C3 1.3962(19) . ?
C2 C7 1.423(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.4259(18) . ?
C6 C8 1.433(2) . ?
C7 C11 1.4376(19) . ?
C8 C9 1.349(2) . ?
C9 C10 1.440(2) . ?
C10 C11 1.421(2) . ?
C10 C12 1.396(2) . ?
C11 C15 1.4303(18) . ?
C12 C13 1.389(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.3991(19) . ?
C15 C16 1.4342(19) . ?
C17 C18 1.4624(18) . ?
C18 C19 1.4034(18) . ?
C18 C23 1.3933(19) . ?
C19 C20 1.3810(19) . ?
C20 C21 1.3919(19) . ?
C21 C22 1.3941(18) . ?
C22 C23 1.3908(19) . ?
C24 C25 1.5154(18) . ?
C25 C26 1.5261(19) . ?
C26 C27 1.5257(18) . ?
C27 C28 1.528(2) . ?
C28 C29 1.538(2) . ?
C29 C30 1.525(2) . ?
C30 C31 1.525(2) . ?
C31 C32 1.525(2) . ?
C32 C33 1.519(2) . ?

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
C21 O1 C24 118.62(10) . . ?
C17 N1 C1 107.04(11) . . ?
C17 N2 C16 105.08(11) . . ?
N1 C1 C2 129.95(12) . . ?
N1 C1 C16 106.22(11) . . ?
C16 C1 C2 123.82(12) . . ?
C3 C2 C1 124.10(13) . . ?
C3 C2 C7 120.45(12) . . ?
C7 C2 C1 115.44(12) . . ?
C4 C3 C2 119.60(14) . . ?
C5 C4 C3 120.97(14) . . ?
C4 C5 C6 121.03(13) . . ?
C5 C6 C7 119.05(13) . . ?
C5 C6 C8 122.04(13) . . ?
C7 C6 C8 118.91(13) . . ?
C2 C7 C6 118.89(13) . . ?
C2 C7 C11 121.61(12) . . ?
C6 C7 C11 119.51(13) . . ?
C9 C8 C6 121.65(13) . . ?
C8 C9 C10 121.18(14) . . ?
C11 C10 C9 118.91(13) . . ?
C12 C10 C9 121.41(13) . . ?
C12 C10 C11 119.67(13) . . ?
C10 C11 C7 119.82(12) . . ?
C10 C11 C15 119.00(13) . . ?
C15 C11 C7 121.17(12) . . ?
C13 C12 C10 120.59(14) . . ?
C14 C13 C12 120.82(14) . . ?
C13 C14 C15 120.33(13) . . ?
C11 C15 C16 116.45(12) . . ?
C14 C15 C11 119.58(13) . . ?
C14 C15 C16 123.96(12) . . ?
N2 C16 C15 128.61(12) . . ?
C1 C16 N2 109.94(11) . . ?
C1 C16 C15 121.45(12) . . ?
N1 C17 C18 123.25(12) . . ?
N2 C17 N1 111.72(11) . . ?
N2 C17 C18 124.99(11) . . ?
C19 C18 C17 119.61(12) . . ?
C23 C18 C17 122.20(12) . . ?
C23 C18 C19 118.17(12) . . ?
C20 C19 C18 120.59(13) . . ?
C19 C20 C21 120.49(12) . . ?
O1 C21 C20 115.91(11) . . ?
O1 C21 C22 124.17(12) . . ?
C20 C21 C22 119.92(12) . . ?
C23 C22 C21 119.08(13) . . ?
C22 C23 C18 121.74(12) . . ?
O1 C24 C25 106.64(10) . . ?
C24 C25 C26 112.91(11) . . ?
C27 C26 C25 111.91(11) . . ?
C26 C27 C28 114.57(11) . . ?
C27 C28 C29 112.69(12) . . ?
C30 C29 C28 114.77(13) . . ?
C29 C30 C31 113.33(13) . . ?
C30 C31 C32 113.50(13) . . ?
C33 C32 C31 113.69(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1W 0.87(2) 1.98(2) 2.8383(16) 173.0(17) . yes
O1W H1WB O2W 0.89(3) 1.95(3) 2.8213(15) 167(2) . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.585
