# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_wb01
_database_code_depnum_ccdc_archive 'CCDC 1960437'
loop_
_audit_author_name
_audit_author_address
bzl
;SCUEC
China
;
_audit_update_record             
;
2019-10-21 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         237.25
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.94040(10)
_cell_length_b                   16.0925(3)
_cell_length_c                   9.1575(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.2540(10)
_cell_angle_gamma                90
_cell_volume                     580.68(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6552
_cell_measurement_theta_min      7.3276
_cell_measurement_theta_max      74.4861
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248

_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            7654
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_theta_min         7.33
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_full        74.48
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             2313
_reflns_number_gt                2261
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0817
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         2313
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.0302P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.099
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2174(4) 0.64293(8) 0.32112(13) 0.0523(3) Uani d . . . 1 . .
C C1 0.4038(4) 0.50554(10) 0.51920(18) 0.0409(4) Uani d . . . 1 . .
O O2 0.5461(4) 0.57424(10) 0.16480(15) 0.0625(4) Uani d . . . 1 . .
C C2 0.5674(5) 0.57492(12) 0.5878(2) 0.0483(4) Uani d . . . 1 . .
H H2 0.62308 0.62151 0.532789 0.058 Uiso calc U . R 1 . .
C C10 -0.0718(5) 0.34901(12) 0.1152(2) 0.0539(5) Uani d . . . 1 . .
H H10 -0.131549 0.343761 0.01726 0.065 Uiso calc U . R 1 . .
C C11 0.0753(5) 0.42044(12) 0.16282(19) 0.0473(4) Uani d . . . 1 . .
H H11 0.113818 0.463635 0.097483 0.057 Uiso calc U . R 1 . .
C C12 0.1712(4) 0.42968(10) 0.31248(18) 0.0404(3) Uani d . . . 1 . .
C C13 0.3176(4) 0.50241(10) 0.37080(18) 0.0400(3) Uani d . . . 1 . .
C C14 0.3786(4) 0.57542(11) 0.27301(17) 0.0434(4) Uani d . . . 1 . .
C C15 0.2551(8) 0.71668(14) 0.2330(3) 0.0702(6) Uani d . . . 1 . .
H H15A 0.491336 0.730543 0.22554 0.105 Uiso calc U . R 1 . .
H H15B 0.135233 0.761896 0.277699 0.105 Uiso calc U . R 1 . .
H H15C 0.163781 0.706652 0.137288 0.105 Uiso calc U . R 1 . .
N N1 0.1838(4) 0.36498(9) 0.55344(17) 0.0472(4) Uani d . . . 1 . .
C C4 0.5612(5) 0.50321(15) 0.81956(19) 0.0552(5) Uani d . . . 1 . .
H H4 0.612072 0.503554 0.918825 0.066 Uiso calc U . R 1 . .
C C3 0.6417(5) 0.57302(14) 0.7327(2) 0.0544(4) Uani d . . . 1 . .
H H3 0.747595 0.618571 0.775611 0.065 Uiso calc U . R 1 . .
C C9 -0.1353(5) 0.28261(13) 0.2120(2) 0.0573(5) Uani d . . . 1 . .
H H9 -0.23636 0.234225 0.177323 0.069 Uiso calc U . R 1 . .
C C5 0.4108(5) 0.43601(13) 0.75914(19) 0.0520(4) Uani d . . . 1 . .
H H5 0.35906 0.39045 0.817406 0.062 Uiso calc U . R 1 . .
C C6 0.3301(5) 0.43396(11) 0.60657(18) 0.0435(4) Uani d . . . 1 . .
C C7 0.1072(4) 0.36235(11) 0.4106(2) 0.0431(4) Uani d . . . 1 . .
C C8 -0.0503(5) 0.28879(12) 0.3551(2) 0.0528(4) Uani d . . . 1 . .
H H8 -0.094881 0.244711 0.417791 0.063 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 . 1.334(2) ?
O1 C15 . 1.443(2) ?
C1 C13 . 1.400(2) ?
C1 C2 . 1.433(2) ?
C1 C6 . 1.433(2) ?
O2 C14 . 1.193(2) ?
C2 C3 . 1.357(3) ?
C2 H2 . 0.93 ?
C10 C11 . 1.359(3) ?
C10 C9 . 1.412(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.428(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.409(2) ?
C12 C7 . 1.431(2) ?
C13 C14 . 1.497(2) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
N1 C6 . 1.341(2) ?
N1 C7 . 1.342(2) ?
C4 C5 . 1.350(3) ?
C4 C3 . 1.414(3) ?
C4 H4 . 0.93 ?
C3 H3 . 0.93 ?
C9 C8 . 1.354(3) ?
C9 H9 . 0.93 ?
C5 C6 . 1.432(2) ?
C5 H5 . 0.93 ?
C7 C8 . 1.429(3) ?
C8 H8 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O1 C15 . . 115.78(15) ?
C13 C1 C2 . . 124.07(16) ?
C13 C1 C6 . . 117.65(15) ?
C2 C1 C6 . . 118.26(15) ?
C3 C2 C1 . . 120.36(18) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C11 C10 C9 . . 121.02(17) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.47(17) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 123.82(15) ?
C13 C12 C7 . . 117.65(14) ?
C11 C12 C7 . . 118.51(16) ?
C1 C13 C12 . . 119.67(15) ?
C1 C13 C14 . . 120.89(15) ?
C12 C13 C14 . . 119.44(14) ?
O2 C14 O1 . . 123.58(17) ?
O2 C14 C13 . . 125.10(16) ?
O1 C14 C13 . . 111.32(13) ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C6 N1 C7 . . 118.31(14) ?
C5 C4 C3 . . 120.32(16) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C2 C3 C4 . . 121.35(19) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C8 C9 C10 . . 120.56(17) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C4 C5 C6 . . 120.89(18) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
N1 C6 C5 . . 117.80(16) ?
N1 C6 C1 . . 123.41(15) ?
C5 C6 C1 . . 118.78(16) ?
N1 C7 C8 . . 117.93(16) ?
N1 C7 C12 . . 123.28(16) ?
C8 C7 C12 . . 118.78(17) ?
C9 C8 C7 . . 120.67(18) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . 179.85(16) ?
C6 C1 C2 C3 . . . . -1.6(3) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C13 . . . . -178.50(17) ?
C10 C11 C12 C7 . . . . -0.3(3) ?
C2 C1 C13 C12 . . . . 177.08(16) ?
C6 C1 C13 C12 . . . . -1.5(2) ?
C2 C1 C13 C14 . . . . -3.0(2) ?
C6 C1 C13 C14 . . . . 178.49(15) ?
C11 C12 C13 C1 . . . . -179.89(15) ?
C7 C12 C13 C1 . . . . 1.9(2) ?
C11 C12 C13 C14 . . . . 0.2(2) ?
C7 C12 C13 C14 . . . . -178.03(13) ?
C15 O1 C14 O2 . . . . 0.3(3) ?
C15 O1 C14 C13 . . . . -179.01(17) ?
C1 C13 C14 O2 . . . . 122.63(19) ?
C12 C13 C14 O2 . . . . -57.4(2) ?
C1 C13 C14 O1 . . . . -58.1(2) ?
C12 C13 C14 O1 . . . . 121.86(16) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C5 C4 C3 C2 . . . . 0.8(3) ?
C11 C10 C9 C8 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C7 N1 C6 C5 . . . . -179.95(16) ?
C7 N1 C6 C1 . . . . 1.1(3) ?
C4 C5 C6 N1 . . . . 179.39(18) ?
C4 C5 C6 C1 . . . . -1.6(3) ?
C13 C1 C6 N1 . . . . -0.1(2) ?
C2 C1 C6 N1 . . . . -178.68(16) ?
C13 C1 C6 C5 . . . . -179.05(16) ?
C2 C1 C6 C5 . . . . 2.3(2) ?
C6 N1 C7 C8 . . . . -179.66(17) ?
C6 N1 C7 C12 . . . . -0.5(2) ?
C13 C12 C7 N1 . . . . -0.9(2) ?
C11 C12 C7 N1 . . . . -179.23(16) ?
C13 C12 C7 C8 . . . . 178.18(15) ?
C11 C12 C7 C8 . . . . -0.1(2) ?
C10 C9 C8 C7 . . . . -0.4(3) ?
N1 C7 C8 C9 . . . . 179.63(17) ?
C12 C7 C8 C9 . . . . 0.5(3) ?

####################################################################### 
# 
# 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_WZF74A
_database_code_depnum_ccdc_archive 'CCDC 1968988'
loop_
_audit_author_name
_audit_author_address
'zilong bian'
;SouthCentral University for Nationalities
China
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.30
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.7602(14)
_cell_length_b                   9.1601(6)
_cell_length_c                   16.7999(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2887.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      5.2658
_cell_measurement_theta_max      78.7741
_cell_measurement_temperature    297.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.138
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200

_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      297.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            30826
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_theta_min         4.71
_diffrn_reflns_theta_max         79.28
_diffrn_reflns_theta_full        79.28
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             5919
_reflns_number_gt                5296
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1266
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_number_reflns         5919
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+0.1732P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.128
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_abs_structure_details 
;

Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(13)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.74791(14) 0.4068(3) 0.47297(15) 0.0665(5) Uani d . . . 1 . .
O O1 0.63104(18) 0.7583(2) 0.6681(2) 0.0931(8) Uani d . . . 1 . .
C C1 0.74067(16) 0.6340(3) 0.54688(18) 0.0626(6) Uani d . . . 1 . .
N N2 0.49938(15) 0.5474(3) 0.52219(16) 0.0700(6) Uani d . . . 1 . .
C C2 0.7659(2) 0.7807(3) 0.5540(3) 0.0785(9) Uani d . . . 1 . .
H H2 0.751718 0.837359 0.597086 0.094 Uiso calc U . R 1 . .
O O4 0.53992(14) 0.3128(3) 0.26387(14) 0.0754(6) Uani d . . . 1 . .
O O3 0.61691(18) 0.1774(2) 0.33520(17) 0.0889(8) Uani d . . . 1 . .
O O2 0.70705(16) 0.6187(3) 0.73657(16) 0.0859(7) Uani d . . . 1 . .
C C3 0.8103(2) 0.8379(4) 0.4988(3) 0.0935(12) Uani d . . . 1 . .
H H3 0.826379 0.93331 0.504419 0.112 Uiso calc U . R 1 . .
C C4 0.8323(3) 0.7544(5) 0.4327(3) 0.0934(11) Uani d . . . 1 . .
H H4 0.862311 0.795568 0.394774 0.112 Uiso calc U . R 1 . .
C C5 0.8101(2) 0.6149(4) 0.4242(2) 0.0834(9) Uani d . . . 1 . .
H H5 0.824844 0.561156 0.38025 0.1 Uiso calc U . R 1 . .
C C6 0.76478(16) 0.5493(3) 0.48137(19) 0.0657(6) Uani d . . . 1 . .
C C7 0.69454(14) 0.5677(3) 0.60181(16) 0.0571(5) Uani d . . . 1 . .
C C8 0.67280(13) 0.4222(3) 0.59210(15) 0.0535(5) Uani d . . . 1 . .
C C9 0.70511(15) 0.3455(3) 0.52644(17) 0.0584(6) Uani d . . . 1 . .
C C10 0.69304(18) 0.1904(3) 0.51859(19) 0.0669(7) Uani d . . . 1 . .
H H10 0.712952 0.140863 0.475683 0.08 Uiso calc U . R 1 . .
C C12 0.61831(16) 0.1888(3) 0.63594(19) 0.0605(6) Uani d . . . 1 . .
C C15 0.57728(19) 0.1076(3) 0.6896(2) 0.0755(8) Uani d . . . 1 . .
H H15 0.575815 0.006498 0.68504 0.091 Uiso calc U . R 1 . .
C C11 0.65408(18) 0.1165(3) 0.5713(2) 0.0679(7) Uani d . . . 1 . .
H H11 0.649911 0.015764 0.566113 0.082 Uiso calc U . R 1 . .
C C13 0.62432(14) 0.3426(3) 0.64434(17) 0.0558(5) Uani d . . . 1 . .
C C16 0.5394(2) 0.1747(4) 0.7483(3) 0.0836(10) Uani d . . . 1 . .
H H16 0.512988 0.1197 0.78423 0.1 Uiso calc U . R 1 . .
C C17 0.5407(2) 0.3262(4) 0.7541(2) 0.0784(9) Uani d . . . 1 . .
H H17 0.513638 0.372477 0.793051 0.094 Uiso calc U . R 1 . .
C C27 0.6760(2) 0.8238(3) 0.3042(3) 0.0775(8) Uani d . . . 1 . .
H H27 0.67943 0.92479 0.308353 0.093 Uiso calc U . R 1 . .
C C18 0.58139(16) 0.4080(3) 0.7030(2) 0.0664(6) Uani d . . . 1 . .
H H18 0.580594 0.509221 0.707236 0.08 Uiso calc U . R 1 . .
C C19 0.67209(19) 0.6590(3) 0.6718(2) 0.0680(7) Uani d . . . 1 . .
C C20 0.6889(4) 0.6948(8) 0.8094(3) 0.127(2) Uani d . . . 1 . .
H H20A 0.706248 0.793295 0.806763 0.19 Uiso calc U . R 1 . .
H H20B 0.710467 0.645819 0.853875 0.19 Uiso calc U . R 1 . .
H H20C 0.638101 0.695693 0.815956 0.19 Uiso calc U . R 1 . .
C C21 0.54406(16) 0.6023(3) 0.46757(17) 0.0599(6) Uani d . . . 1 . .
C C22 0.57538(14) 0.5188(3) 0.40475(16) 0.0575(5) Uani d . . . 1 . .
C C23 0.62533(15) 0.5934(3) 0.35040(18) 0.0593(6) Uani d . . . 1 . .
C C24 0.63265(18) 0.7464(3) 0.3577(2) 0.0638(7) Uani d . . . 1 . .
C C25 0.5976(2) 0.8255(3) 0.4198(2) 0.0728(7) Uani d . . . 1 . .
H H25 0.602952 0.926286 0.422812 0.087 Uiso calc U . R 1 . .
C C26 0.5571(2) 0.7565(3) 0.4736(2) 0.0738(8) Uani d . . . 1 . .
H H26 0.537204 0.809003 0.515444 0.089 Uiso calc U . R 1 . .
C C28 0.7133(2) 0.7523(4) 0.2458(3) 0.0879(11) Uani d . . . 1 . .
H H28 0.740608 0.804438 0.209399 0.105 Uiso calc U . R 1 . .
C C31 0.55395(14) 0.3740(3) 0.39802(17) 0.0594(5) Uani d . . . 1 . .
C C30 0.66665(18) 0.5240(3) 0.2931(2) 0.0731(7) Uani d . . . 1 . .
H H30 0.665147 0.422769 0.289471 0.088 Uiso calc U . R 1 . .
C C29 0.7096(2) 0.6004(4) 0.2416(3) 0.0858(10) Uani d . . . 1 . .
H H29 0.736451 0.550578 0.203843 0.103 Uiso calc U . R 1 . .
C C33 0.48176(16) 0.4034(3) 0.51770(19) 0.0657(6) Uani d . . . 1 . .
C C34 0.4356(2) 0.3440(5) 0.5758(3) 0.0842(9) Uani d . . . 1 . .
H H34 0.418905 0.402908 0.616861 0.101 Uiso calc U . R 1 . .
C C35 0.4158(2) 0.2040(5) 0.5725(3) 0.0959(12) Uani d . . . 1 . .
H H35 0.385419 0.166857 0.611228 0.115 Uiso calc U . R 1 . .
C C36 0.4400(2) 0.1124(4) 0.5117(3) 0.0934(11) Uani d . . . 1 . .
H H36 0.425831 0.015124 0.510791 0.112 Uiso calc U . R 1 . .
C C37 0.4845(2) 0.1647(4) 0.4533(3) 0.0782(8) Uani d . . . 1 . .
H H37 0.499757 0.103458 0.412543 0.094 Uiso calc U . R 1 . .
C C38 0.57503(17) 0.2769(3) 0.32991(19) 0.0645(6) Uani d . . . 1 . .
C C39 0.5580(3) 0.2299(5) 0.1933(3) 0.0981(12) Uani d . . . 1 . .
H H39A 0.552444 0.127546 0.203905 0.147 Uiso calc U . R 1 . .
H H39B 0.606604 0.249411 0.178713 0.147 Uiso calc U . R 1 . .
H H39C 0.527095 0.257741 0.150362 0.147 Uiso calc U . R 1 . .
C C32 0.50729(16) 0.3137(3) 0.45537(18) 0.0628(6) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9 . 1.329(4) ?
N1 C6 . 1.351(4) ?
O1 C19 . 1.193(4) ?
C1 C7 . 1.403(4) ?
C1 C6 . 1.421(4) ?
C1 C2 . 1.429(4) ?
N2 C21 . 1.341(4) ?
N2 C33 . 1.362(4) ?
C2 C3 . 1.351(6) ?
C2 H2 . 0.93 ?
O4 C38 . 1.331(4) ?
O4 C39 . 1.449(5) ?
O3 C38 . 1.206(4) ?
O2 C19 . 1.323(5) ?
O2 C20 . 1.449(5) ?
C3 C4 . 1.410(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.352(6) ?
C4 H4 . 0.93 ?
C5 C6 . 1.416(5) ?
C5 H5 . 0.93 ?
C7 C8 . 1.404(3) ?
C7 C19 . 1.503(4) ?
C8 C9 . 1.441(4) ?
C8 C13 . 1.459(4) ?
C9 C10 . 1.445(4) ?
C10 C11 . 1.332(5) ?
C10 H10 . 0.93 ?
C12 C15 . 1.399(5) ?
C12 C13 . 1.420(3) ?
C12 C11 . 1.439(4) ?
C15 C16 . 1.362(6) ?
C15 H15 . 0.93 ?
C11 H11 . 0.93 ?
C13 C18 . 1.407(4) ?
C16 C17 . 1.391(5) ?
C16 H16 . 0.93 ?
C17 C18 . 1.372(5) ?
C17 H17 . 0.93 ?
C27 C28 . 1.371(6) ?
C27 C24 . 1.405(5) ?
C27 H27 . 0.93 ?
C18 H18 . 0.93 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 C22 . 1.430(4) ?
C21 C26 . 1.437(4) ?
C22 C31 . 1.391(4) ?
C22 C23 . 1.476(4) ?
C23 C30 . 1.390(5) ?
C23 C24 . 1.413(4) ?
C24 C25 . 1.430(5) ?
C25 C26 . 1.339(5) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?
C28 C29 . 1.395(6) ?
C28 H28 . 0.93 ?
C31 C32 . 1.414(4) ?
C31 C38 . 1.503(4) ?
C30 C29 . 1.374(5) ?
C30 H30 . 0.93 ?
C29 H29 . 0.93 ?
C33 C34 . 1.414(5) ?
C33 C32 . 1.415(5) ?
C34 C35 . 1.337(6) ?
C34 H34 . 0.93 ?
C35 C36 . 1.396(8) ?
C35 H35 . 0.93 ?
C36 C37 . 1.375(6) ?
C36 H36 . 0.93 ?
C37 C32 . 1.430(4) ?
C37 H37 . 0.93 ?
C39 H39A . 0.96 ?
C39 H39B . 0.96 ?
C39 H39C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C6 . . 118.6(2) ?
C7 C1 C6 . . 118.0(2) ?
C7 C1 C2 . . 123.8(3) ?
C6 C1 C2 . . 118.2(3) ?
C21 N2 C33 . . 118.5(3) ?
C3 C2 C1 . . 120.7(4) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C38 O4 C39 . . 115.9(3) ?
C19 O2 C20 . . 116.4(4) ?
C2 C3 C4 . . 120.7(4) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 120.3(4) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 121.0(4) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
N1 C6 C5 . . 118.7(3) ?
N1 C6 C1 . . 122.3(3) ?
C5 C6 C1 . . 119.0(3) ?
C1 C7 C8 . . 120.9(2) ?
C1 C7 C19 . . 116.5(2) ?
C8 C7 C19 . . 122.5(3) ?
C7 C8 C9 . . 115.4(2) ?
C7 C8 C13 . . 125.9(2) ?
C9 C8 C13 . . 118.6(2) ?
N1 C9 C8 . . 124.4(2) ?
N1 C9 C10 . . 116.6(2) ?
C8 C9 C10 . . 118.9(3) ?
C11 C10 C9 . . 121.7(3) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C15 C12 C13 . . 120.5(3) ?
C15 C12 C11 . . 119.9(2) ?
C13 C12 C11 . . 119.7(3) ?
C16 C15 C12 . . 120.9(3) ?
C16 C15 H15 . . 119.6 ?
C12 C15 H15 . . 119.6 ?
C10 C11 C12 . . 121.6(2) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
C18 C13 C12 . . 116.5(3) ?
C18 C13 C8 . . 124.4(2) ?
C12 C13 C8 . . 119.0(2) ?
C15 C16 C17 . . 119.5(3) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C18 C17 C16 . . 120.7(3) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C28 C27 C24 . . 120.8(3) ?
C28 C27 H27 . . 119.6 ?
C24 C27 H27 . . 119.6 ?
C17 C18 C13 . . 121.6(3) ?
C17 C18 H18 . . 119.2 ?
C13 C18 H18 . . 119.2 ?
O1 C19 O2 . . 125.2(3) ?
O1 C19 C7 . . 124.3(3) ?
O2 C19 C7 . . 110.4(3) ?
O2 C20 H20A . . 109.5 ?
O2 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O2 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N2 C21 C22 . . 124.2(2) ?
N2 C21 C26 . . 115.3(3) ?
C22 C21 C26 . . 120.5(3) ?
C31 C22 C21 . . 116.8(3) ?
C31 C22 C23 . . 125.1(2) ?
C21 C22 C23 . . 118.0(2) ?
C30 C23 C24 . . 117.3(3) ?
C30 C23 C22 . . 124.8(2) ?
C24 C23 C22 . . 117.8(3) ?
C27 C24 C23 . . 120.1(3) ?
C27 C24 C25 . . 118.5(3) ?
C23 C24 C25 . . 121.4(3) ?
C26 C25 C24 . . 120.9(2) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C21 . . 120.9(3) ?
C25 C26 H26 . . 119.6 ?
C21 C26 H26 . . 119.6 ?
C27 C28 C29 . . 119.2(3) ?
C27 C28 H28 . . 120.4 ?
C29 C28 H28 . . 120.4 ?
C22 C31 C32 . . 119.8(3) ?
C22 C31 C38 . . 123.4(3) ?
C32 C31 C38 . . 116.8(2) ?
C29 C30 C23 . . 122.0(3) ?
C29 C30 H30 . . 119.0 ?
C23 C30 H30 . . 119.0 ?
C30 C29 C28 . . 120.4(3) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
N2 C33 C34 . . 118.9(3) ?
N2 C33 C32 . . 121.4(3) ?
C34 C33 C32 . . 119.6(3) ?
C35 C34 C33 . . 120.7(4) ?
C35 C34 H34 . . 119.6 ?
C33 C34 H34 . . 119.6 ?
C34 C35 C36 . . 121.1(4) ?
C34 C35 H35 . . 119.4 ?
C36 C35 H35 . . 119.4 ?
C37 C36 C35 . . 120.6(3) ?
C37 C36 H36 . . 119.7 ?
C35 C36 H36 . . 119.7 ?
C36 C37 C32 . . 119.8(4) ?
C36 C37 H37 . . 120.1 ?
C32 C37 H37 . . 120.1 ?
O3 C38 O4 . . 124.7(3) ?
O3 C38 C31 . . 124.2(3) ?
O4 C38 C31 . . 111.0(2) ?
O4 C39 H39A . . 109.5 ?
O4 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
O4 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C31 C32 C33 . . 119.1(3) ?
C31 C32 C37 . . 122.8(3) ?
C33 C32 C37 . . 118.1(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 C3 . . . . -179.9(3) ?
C6 C1 C2 C3 . . . . 1.5(5) ?
C1 C2 C3 C4 . . . . 0.3(6) ?
C2 C3 C4 C5 . . . . -0.9(7) ?
C3 C4 C5 C6 . . . . -0.4(7) ?
C9 N1 C6 C5 . . . . -179.7(3) ?
C9 N1 C6 C1 . . . . 2.5(4) ?
C4 C5 C6 N1 . . . . -175.7(4) ?
C4 C5 C6 C1 . . . . 2.1(6) ?
C7 C1 C6 N1 . . . . -3.6(4) ?
C2 C1 C6 N1 . . . . 175.1(3) ?
C7 C1 C6 C5 . . . . 178.6(3) ?
C2 C1 C6 C5 . . . . -2.7(4) ?
C6 C1 C7 C8 . . . . -0.1(4) ?
C2 C1 C7 C8 . . . . -178.8(3) ?
C6 C1 C7 C19 . . . . 178.0(3) ?
C2 C1 C7 C19 . . . . -0.6(4) ?
C1 C7 C8 C9 . . . . 4.4(3) ?
C19 C7 C8 C9 . . . . -173.6(3) ?
C1 C7 C8 C13 . . . . -178.9(2) ?
C19 C7 C8 C13 . . . . 3.0(4) ?
C6 N1 C9 C8 . . . . 2.4(4) ?
C6 N1 C9 C10 . . . . -175.3(3) ?
C7 C8 C9 N1 . . . . -5.8(4) ?
C13 C8 C9 N1 . . . . 177.3(2) ?
C7 C8 C9 C10 . . . . 171.8(2) ?
C13 C8 C9 C10 . . . . -5.0(4) ?
N1 C9 C10 C11 . . . . 176.5(3) ?
C8 C9 C10 C11 . . . . -1.4(4) ?
C13 C12 C15 C16 . . . . 3.4(5) ?
C11 C12 C15 C16 . . . . -176.0(4) ?
C9 C10 C11 C12 . . . . 4.0(5) ?
C15 C12 C11 C10 . . . . 179.3(3) ?
C13 C12 C11 C10 . . . . 0.0(5) ?
C15 C12 C13 C18 . . . . -6.6(4) ?
C11 C12 C13 C18 . . . . 172.7(3) ?
C15 C12 C13 C8 . . . . 174.3(3) ?
C11 C12 C13 C8 . . . . -6.4(4) ?
C7 C8 C13 C18 . . . . 13.2(4) ?
C9 C8 C13 C18 . . . . -170.3(3) ?
C7 C8 C13 C12 . . . . -167.7(2) ?
C9 C8 C13 C12 . . . . 8.8(3) ?
C12 C15 C16 C17 . . . . 1.1(6) ?
C15 C16 C17 C18 . . . . -2.1(6) ?
C16 C17 C18 C13 . . . . -1.4(6) ?
C12 C13 C18 C17 . . . . 5.6(4) ?
C8 C13 C18 C17 . . . . -175.2(3) ?
C20 O2 C19 O1 . . . . 5.3(6) ?
C20 O2 C19 C7 . . . . -178.1(4) ?
C1 C7 C19 O1 . . . . 72.8(4) ?
C8 C7 C19 O1 . . . . -109.0(4) ?
C1 C7 C19 O2 . . . . -103.8(3) ?
C8 C7 C19 O2 . . . . 74.3(4) ?
C33 N2 C21 C22 . . . . -0.7(4) ?
C33 N2 C21 C26 . . . . 176.8(3) ?
N2 C21 C22 C31 . . . . 4.2(4) ?
C26 C21 C22 C31 . . . . -173.2(3) ?
N2 C21 C22 C23 . . . . -178.2(2) ?
C26 C21 C22 C23 . . . . 4.4(4) ?
C31 C22 C23 C30 . . . . -11.0(4) ?
C21 C22 C23 C30 . . . . 171.6(3) ?
C31 C22 C23 C24 . . . . 169.9(3) ?
C21 C22 C23 C24 . . . . -7.5(3) ?
C28 C27 C24 C23 . . . . -1.9(5) ?
C28 C27 C24 C25 . . . . 177.1(4) ?
C30 C23 C24 C27 . . . . 5.0(4) ?
C22 C23 C24 C27 . . . . -175.9(3) ?
C30 C23 C24 C25 . . . . -174.0(3) ?
C22 C23 C24 C25 . . . . 5.1(4) ?
C27 C24 C25 C26 . . . . -178.3(3) ?
C23 C24 C25 C26 . . . . 0.7(5) ?
C24 C25 C26 C21 . . . . -4.0(6) ?
N2 C21 C26 C25 . . . . -176.2(3) ?
C22 C21 C26 C25 . . . . 1.4(5) ?
C24 C27 C28 C29 . . . . -2.1(6) ?
C21 C22 C31 C32 . . . . -4.4(4) ?
C23 C22 C31 C32 . . . . 178.1(2) ?
C21 C22 C31 C38 . . . . 172.6(2) ?
C23 C22 C31 C38 . . . . -4.9(4) ?
C24 C23 C30 C29 . . . . -4.2(5) ?
C22 C23 C30 C29 . . . . 176.8(3) ?
C23 C30 C29 C28 . . . . 0.3(6) ?
C27 C28 C29 C30 . . . . 3.0(7) ?
C21 N2 C33 C34 . . . . 178.9(3) ?
C21 N2 C33 C32 . . . . -2.5(4) ?
N2 C33 C34 C35 . . . . 178.5(4) ?
C32 C33 C34 C35 . . . . -0.1(6) ?
C33 C34 C35 C36 . . . . 0.0(7) ?
C34 C35 C36 C37 . . . . -0.5(7) ?
C35 C36 C37 C32 . . . . 1.0(6) ?
C39 O4 C38 O3 . . . . -4.1(5) ?
C39 O4 C38 C31 . . . . 177.7(3) ?
C22 C31 C38 O3 . . . . 108.3(4) ?
C32 C31 C38 O3 . . . . -74.6(4) ?
C22 C31 C38 O4 . . . . -73.4(4) ?
C32 C31 C38 O4 . . . . 103.6(3) ?
C22 C31 C32 C33 . . . . 1.6(4) ?
C38 C31 C32 C33 . . . . -175.6(2) ?
C22 C31 C32 C37 . . . . -178.4(3) ?
C38 C31 C32 C37 . . . . 4.4(4) ?
N2 C33 C32 C31 . . . . 2.1(4) ?
C34 C33 C32 C31 . . . . -179.4(3) ?
N2 C33 C32 C37 . . . . -178.0(3) ?
C34 C33 C32 C37 . . . . 0.6(4) ?
C36 C37 C32 C31 . . . . 178.9(3) ?
C36 C37 C32 C33 . . . . -1.1(5) ?

