# 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 2023

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

data_3b
_database_code_depnum_ccdc_archive 'CCDC 2177753'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C40 H27 N3 O2), C H Cl3'
_chemical_formula_sum            'C81 H55 Cl3 N6 O4'
_chemical_formula_weight         1282.66

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'
Cl Cl 0.1484 0.1585 '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                   13.705(3)
_cell_length_b                   13.864(3)
_cell_length_c                   17.875(5)
_cell_angle_alpha                85.290(7)
_cell_angle_beta                 74.680(7)
_cell_angle_gamma                82.395(7)
_cell_volume                     3242.8(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.14

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            42255
_diffrn_reflns_av_unetI/netI     0.3562
_diffrn_reflns_av_R_equivalents  0.2825
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11395
_reflns_number_gt                3740
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0085(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11395
_refine_ls_number_parameters     850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3352
_refine_ls_R_factor_gt           0.1218
_refine_ls_wR_factor_ref         0.2998
_refine_ls_wR_factor_gt          0.2426
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1529(6) 0.4704(5) 0.6524(4) 0.059(2) Uani 1 1 d . . . . .
H1A H 0.1777 0.4880 0.5982 0.089 Uiso 1 1 calc R U . . .
H1B H 0.2081 0.4636 0.6769 0.089 Uiso 1 1 calc R U . . .
H1C H 0.1013 0.5202 0.6765 0.089 Uiso 1 1 calc R U . . .
C2 C 0.0405(5) 0.3482(6) 0.7286(5) 0.0429(19) Uani 1 1 d . . . . .
C3 C 0.0104(6) 0.3937(6) 0.7984(5) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.0318 0.4530 0.8037 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0522(7) 0.3474(7) 0.8592(5) 0.067(2) Uani 1 1 d . . . . .
H4 H -0.0722 0.3744 0.9076 0.080 Uiso 1 1 calc R U . . .
C5 C -0.0865(6) 0.2594(7) 0.8493(5) 0.059(2) Uani 1 1 d . . . . .
H5 H -0.1286 0.2287 0.8915 0.070 Uiso 1 1 calc R U . . .
C6 C -0.0592(5) 0.2179(6) 0.7786(5) 0.048(2) Uani 1 1 d . . . . .
H6 H -0.0831 0.1598 0.7734 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0048(5) 0.2626(5) 0.7139(4) 0.0347(18) Uani 1 1 d . . . . .
C8 C 0.0482(5) 0.2440(5) 0.6343(4) 0.0360(18) Uani 1 1 d . . . . .
C9 C 0.1152(5) 0.3142(5) 0.6047(4) 0.0374(18) Uani 1 1 d . . . . .
C10 C 0.4793(6) 0.4218(6) 0.4044(5) 0.061(2) Uani 1 1 d . . . . .
H10 H 0.4345 0.4707 0.4320 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5787(7) 0.4402(7) 0.3694(5) 0.069(3) Uani 1 1 d . . . . .
H11 H 0.6016 0.4988 0.3748 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6409(7) 0.3687(9) 0.3269(6) 0.089(3) Uani 1 1 d . . . . .
H12 H 0.7077 0.3795 0.3024 0.107 Uiso 1 1 calc R U . . .
C13 C 0.6093(7) 0.2818(9) 0.3189(6) 0.096(3) Uani 1 1 d . . . . .
H13 H 0.6534 0.2346 0.2887 0.115 Uiso 1 1 calc R U . . .
C14 C 0.5083(7) 0.2646(7) 0.3571(5) 0.082(3) Uani 1 1 d . . . . .
H14 H 0.4850 0.2057 0.3531 0.099 Uiso 1 1 calc R U . . .
C15 C 0.4452(6) 0.3370(6) 0.4003(4) 0.050(2) Uani 1 1 d . . . . .
C16 C 0.2956(5) 0.3343(5) 0.5155(4) 0.0428(19) Uani 1 1 d . . . . .
C17 C 0.1864(5) 0.3159(5) 0.5296(4) 0.0367(18) Uani 1 1 d . . . . .
C18 C 0.1741(5) 0.2881(5) 0.4623(4) 0.0388(18) Uani 1 1 d . . . . .
C19 C 0.2718(5) 0.2909(5) 0.4023(4) 0.0402(19) Uani 1 1 d . . . . .
C20 C -0.0475(5) 0.2213(5) 0.4078(4) 0.0367(18) Uani 1 1 d . . . . .
C21 C -0.1123(5) 0.2189(5) 0.3591(4) 0.0455(19) Uani 1 1 d . . . . .
H21 H -0.1720 0.1893 0.3751 0.055 Uiso 1 1 calc R U . . .
C22 C -0.0821(6) 0.2629(5) 0.2863(5) 0.052(2) Uani 1 1 d . . . . .
H22 H -0.1217 0.2616 0.2515 0.062 Uiso 1 1 calc R U . . .
C23 C 0.0063(6) 0.3095(5) 0.2628(4) 0.052(2) Uani 1 1 d . . . . .
H23 H 0.0236 0.3391 0.2132 0.062 Uiso 1 1 calc R U . . .
C24 C 0.0684(5) 0.3124(5) 0.3119(4) 0.044(2) Uani 1 1 d . . . . .
H24 H 0.1273 0.3432 0.2963 0.053 Uiso 1 1 calc R U . . .
C25 C 0.0392(5) 0.2672(5) 0.3863(4) 0.0363(18) Uani 1 1 d . . . . .
C26 C 0.0841(5) 0.2551(5) 0.4521(4) 0.0342(18) Uani 1 1 d . . . . .
C27 C 0.0219(5) 0.2008(5) 0.5099(4) 0.0333(17) Uani 1 1 d . . . . .
C28 C -0.0365(6) 0.0095(5) 0.6625(4) 0.053(2) Uani 1 1 d . . . . .
H28 H 0.0280 -0.0253 0.6542 0.063 Uiso 1 1 calc R U . . .
C29 C -0.1207(9) -0.0348(6) 0.7053(5) 0.076(3) Uani 1 1 d . . . . .
H29 H -0.1115 -0.0985 0.7253 0.091 Uiso 1 1 calc R U . . .
C30 C -0.2181(7) 0.0146(7) 0.7186(5) 0.072(3) Uani 1 1 d . . . . .
H30 H -0.2743 -0.0155 0.7465 0.086 Uiso 1 1 calc R U . . .
C31 C -0.2294(7) 0.1087(7) 0.6896(5) 0.058(2) Uani 1 1 d . . . . .
H31 H -0.2944 0.1426 0.6984 0.070 Uiso 1 1 calc R U . . .
C32 C -0.1476(6) 0.1544(6) 0.6476(4) 0.047(2) Uani 1 1 d . . . . .
H32 H -0.1577 0.2187 0.6293 0.057 Uiso 1 1 calc R U . . .
C33 C -0.0468(5) 0.1040(5) 0.6321(4) 0.0400(19) Uani 1 1 d . . . . .
C34 C 0.0390(5) 0.1596(5) 0.5878(4) 0.0356(18) Uani 1 1 d . . . . .
C35 C 0.1430(5) 0.0912(5) 0.5689(4) 0.0376(18) Uani 1 1 d . . . . .
C36 C 0.1745(5) 0.0389(5) 0.5035(4) 0.047(2) Uani 1 1 d . . . . .
H36 H 0.1330 0.0428 0.4694 0.057 Uiso 1 1 calc R U . . .
C37 C 0.2679(6) -0.0205(6) 0.4867(5) 0.064(2) Uani 1 1 d . . . . .
H37 H 0.2893 -0.0537 0.4410 0.076 Uiso 1 1 calc R U . . .
C38 C 0.3260(6) -0.0290(6) 0.5372(5) 0.074(3) Uani 1 1 d . . . . .
H38 H 0.3874 -0.0693 0.5268 0.088 Uiso 1 1 calc R U . . .
C39 C 0.2958(7) 0.0209(7) 0.6038(5) 0.088(3) Uani 1 1 d . . . . .
H39 H 0.3361 0.0146 0.6388 0.105 Uiso 1 1 calc R U . . .
C40 C 0.2044(6) 0.0809(6) 0.6185(4) 0.071(3) Uani 1 1 d . . . . .
H40 H 0.1842 0.1153 0.6637 0.085 Uiso 1 1 calc R U . . .
C41 C 0.4255(6) 0.7052(5) 0.4249(4) 0.062(2) Uani 1 1 d . . . . .
H41A H 0.4967 0.7126 0.4067 0.092 Uiso 1 1 calc R U . . .
H41B H 0.4143 0.6627 0.4708 0.092 Uiso 1 1 calc R U . . .
H41C H 0.3874 0.7677 0.4367 0.092 Uiso 1 1 calc R U . . .
C42 C 0.3022(6) 0.6192(5) 0.3790(4) 0.0419(19) Uani 1 1 d . . . . .
C43 C 0.2279(7) 0.6156(5) 0.4484(4) 0.051(2) Uani 1 1 d . . . . .
H43 H 0.2351 0.6404 0.4931 0.062 Uiso 1 1 calc R U . . .
C44 C 0.1430(6) 0.5736(5) 0.4477(5) 0.056(2) Uani 1 1 d . . . . .
H44 H 0.0907 0.5703 0.4929 0.068 Uiso 1 1 calc R U . . .
C45 C 0.1345(6) 0.5361(5) 0.3809(5) 0.057(2) Uani 1 1 d . . . . .
H45 H 0.0759 0.5083 0.3823 0.068 Uiso 1 1 calc R U . . .
C46 C 0.2098(6) 0.5382(5) 0.3118(4) 0.048(2) Uani 1 1 d . . . . .
H46 H 0.2008 0.5148 0.2671 0.058 Uiso 1 1 calc R U . . .
C47 C 0.2998(5) 0.5765(5) 0.3108(4) 0.0379(18) Uani 1 1 d . . . . .
C48 C 0.3905(5) 0.5938(5) 0.2530(4) 0.0398(18) Uani 1 1 d . . . . .
C49 C 0.4443(5) 0.6480(5) 0.2885(4) 0.0388(18) Uani 1 1 d . . . . .
C50 C 0.6381(8) 0.9809(7) 0.1880(5) 0.076(3) Uani 1 1 d . . . . .
H50 H 0.5692 0.9827 0.1909 0.091 Uiso 1 1 calc R U . . .
C51 C 0.6841(11) 1.0665(8) 0.1769(6) 0.098(3) Uani 1 1 d . . . . .
H51 H 0.6455 1.1262 0.1729 0.118 Uiso 1 1 calc R U . . .
C52 C 0.7886(12) 1.0629(9) 0.1718(6) 0.103(4) Uani 1 1 d . . . . .
H52 H 0.8191 1.1202 0.1650 0.124 Uiso 1 1 calc R U . . .
C53 C 0.8444(9) 0.9761(10) 0.1769(5) 0.088(3) Uani 1 1 d . . . . .
H53 H 0.9137 0.9745 0.1724 0.105 Uiso 1 1 calc R U . . .
C54 C 0.8021(7) 0.8906(7) 0.1884(4) 0.062(2) Uani 1 1 d . . . . .
H54 H 0.8419 0.8316 0.1922 0.075 Uiso 1 1 calc R U . . .
C55 C 0.6971(7) 0.8932(6) 0.1945(4) 0.057(2) Uani 1 1 d . . . . .
C56 C 0.5556(6) 0.7905(6) 0.2583(5) 0.053(2) Uani 1 1 d . . . . .
C57 C 0.5384(5) 0.6905(5) 0.2493(4) 0.0422(19) Uani 1 1 d . . . . .
C58 C 0.6148(6) 0.6496(5) 0.1939(4) 0.044(2) Uani 1 1 d . . . . .
C59 C 0.6898(7) 0.7218(6) 0.1663(5) 0.057(2) Uani 1 1 d . . . . .
C60 C 0.6718(6) 0.4090(5) 0.1082(4) 0.0416(19) Uani 1 1 d . . . . .
C61 C 0.7316(7) 0.3266(6) 0.0765(4) 0.059(2) Uani 1 1 d . . . . .
H61 H 0.7041 0.2762 0.0608 0.070 Uiso 1 1 calc R U . . .
C62 C 0.8372(7) 0.3236(6) 0.0693(4) 0.059(2) Uani 1 1 d . . . . .
H62 H 0.8811 0.2692 0.0497 0.071 Uiso 1 1 calc R U . . .
C63 C 0.8757(6) 0.4012(6) 0.0914(5) 0.064(2) Uani 1 1 d . . . . .
H63 H 0.9457 0.3984 0.0847 0.077 Uiso 1 1 calc R U . . .
C64 C 0.8138(6) 0.4830(6) 0.1232(4) 0.056(2) Uani 1 1 d . . . . .
H64 H 0.8411 0.5336 0.1387 0.067 Uiso 1 1 calc R U . . .
C65 C 0.7087(5) 0.4871(5) 0.1312(4) 0.0404(19) Uani 1 1 d . . . . .
C66 C 0.6221(5) 0.5573(5) 0.1618(4) 0.0396(19) Uani 1 1 d . . . . .
C67 C 0.5386(5) 0.5185(5) 0.1530(4) 0.0413(19) Uani 1 1 d . . . . .
C68 C 0.4960(6) 0.6744(5) 0.0443(4) 0.048(2) Uani 1 1 d . . . . .
H68 H 0.5440 0.6220 0.0261 0.058 Uiso 1 1 calc R U . . .
C69 C 0.4955(7) 0.7603(6) -0.0016(5) 0.066(2) Uani 1 1 d . . . . .
H69 H 0.5433 0.7663 -0.0491 0.079 Uiso 1 1 calc R U . . .
C70 C 0.4218(7) 0.8366(6) 0.0252(5) 0.062(2) Uani 1 1 d . . . . .
H70 H 0.4186 0.8941 -0.0052 0.075 Uiso 1 1 calc R U . . .
C71 C 0.3546(7) 0.8286(6) 0.0951(5) 0.069(3) Uani 1 1 d . . . . .
H71 H 0.3072 0.8817 0.1127 0.083 Uiso 1 1 calc R U . . .
C72 C 0.3543(6) 0.7438(6) 0.1413(4) 0.052(2) Uani 1 1 d . . . . .
H72 H 0.3060 0.7393 0.1887 0.062 Uiso 1 1 calc R U . . .
C73 C 0.4280(5) 0.6639(5) 0.1159(4) 0.0409(19) Uani 1 1 d . . . . .
C74 C 0.4268(5) 0.5699(5) 0.1681(4) 0.0367(18) Uani 1 1 d . . . . .
C75 C 0.3618(5) 0.4988(5) 0.1472(4) 0.0388(18) Uani 1 1 d . . . . .
C76 C 0.3065(5) 0.5250(6) 0.0921(4) 0.050(2) Uani 1 1 d . . . . .
H76 H 0.3073 0.5872 0.0683 0.060 Uiso 1 1 calc R U . . .
C77 C 0.2505(6) 0.4598(6) 0.0726(5) 0.063(2) Uani 1 1 d . . . . .
H77 H 0.2158 0.4776 0.0344 0.075 Uiso 1 1 calc R U . . .
C78 C 0.2457(6) 0.3702(7) 0.1085(5) 0.058(2) Uani 1 1 d . . . . .
H78 H 0.2067 0.3273 0.0956 0.070 Uiso 1 1 calc R U . . .
C79 C 0.2995(6) 0.3414(6) 0.1655(4) 0.058(2) Uani 1 1 d . . . . .
H79 H 0.2978 0.2793 0.1895 0.070 Uiso 1 1 calc R U . . .
C80 C 0.3541(5) 0.4069(6) 0.1845(4) 0.046(2) Uani 1 1 d . . . . .
H80 H 0.3873 0.3895 0.2236 0.055 Uiso 1 1 calc R U . . .
C1S C 0.8385(7) 0.9036(6) 0.9756(5) 0.080(3) Uani 1 1 d . . . . .
H1S H 0.8396 0.8803 1.0287 0.097 Uiso 1 1 calc R U . . .
Cl1S Cl 0.8700(3) 1.0202(2) 0.9621(2) 0.1382(12) Uani 1 1 d . . . . .
Cl2S Cl 0.7190(2) 0.8967(2) 0.9648(2) 0.1421(13) Uani 1 1 d . . . . .
Cl3S Cl 0.9281(2) 0.8286(2) 0.9119(3) 0.1683(16) Uani 1 1 d . . . . .
N1 N 0.1099(4) 0.3783(4) 0.6609(3) 0.0393(15) Uani 1 1 d . . . . .
N2 N 0.3415(4) 0.3222(4) 0.4376(3) 0.0461(16) Uani 1 1 d . . . . .
N3 N -0.0583(4) 0.1800(4) 0.4829(3) 0.0378(14) Uani 1 1 d . . . . .
H3A H -0.1067 0.1472 0.5082 0.045 Uiso 1 1 calc R U . . .
N4 N 0.3921(5) 0.6631(4) 0.3642(3) 0.0438(16) Uani 1 1 d . . . . .
N5 N 0.6513(5) 0.8052(5) 0.2077(4) 0.0538(17) Uani 1 1 d . . . . .
N6 N 0.5668(4) 0.4316(4) 0.1199(3) 0.0433(15) Uani 1 1 d . . . . .
H6A H 0.5267 0.3961 0.1080 0.052 Uiso 1 1 calc R U . . .
O1 O 0.3388(4) 0.3554(4) 0.5618(3) 0.0641(16) Uani 1 1 d . . . . .
O2 O 0.2917(3) 0.2678(4) 0.3357(3) 0.0550(14) Uani 1 1 d . . . . .
O3 O 0.5023(4) 0.8551(4) 0.2981(3) 0.0681(16) Uani 1 1 d . . . . .
O4 O 0.7689(5) 0.7122(4) 0.1154(3) 0.0712(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.456(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.383(9) . ?
C2 N1 1.400(9) . ?
C2 C7 1.410(9) . ?
C3 C4 1.367(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.421(9) . ?
C8 C9 1.402(9) . ?
C8 C34 1.527(9) . ?
C9 N1 1.376(8) . ?
C9 C17 1.436(9) . ?
C10 C15 1.335(9) . ?
C10 C11 1.388(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.413(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(10) . ?
C14 H14 0.9300 . ?
C15 N2 1.436(9) . ?
C16 O1 1.210(7) . ?
C16 N2 1.382(8) . ?
C16 C17 1.503(9) . ?
C17 C18 1.351(8) . ?
C18 C26 1.432(9) . ?
C18 C19 1.480(9) . ?
C19 O2 1.209(7) . ?
C19 N2 1.405(8) . ?
C20 C25 1.372(9) . ?
C20 N3 1.394(8) . ?
C20 C21 1.404(9) . ?
C21 C22 1.374(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.404(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.452(8) . ?
C26 C27 1.392(8) . ?
C27 N3 1.383(7) . ?
C27 C34 1.524(9) . ?
C28 C33 1.381(9) . ?
C28 C29 1.392(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(11) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.374(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.430(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.501(9) . ?
C34 C35 1.576(9) . ?
C35 C40 1.361(9) . ?
C35 C36 1.368(8) . ?
C36 C37 1.402(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.342(9) . ?
C37 H37 0.9300 . ?
C38 C39 1.366(10) . ?
C38 H38 0.9300 . ?
C39 C40 1.385(10) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 N4 1.471(8) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.384(10) . ?
C42 N4 1.399(9) . ?
C42 C47 1.408(8) . ?
C43 C44 1.371(10) . ?
C43 H43 0.9300 . ?
C44 C45 1.379(9) . ?
C44 H44 0.9300 . ?
C45 C46 1.386(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.400(9) . ?
C46 H46 0.9300 . ?
C47 C48 1.425(9) . ?
C48 C49 1.407(9) . ?
C48 C74 1.517(9) . ?
C49 N4 1.373(8) . ?
C49 C57 1.468(10) . ?
C50 C55 1.382(11) . ?
C50 C51 1.391(12) . ?
C50 H50 0.9300 . ?
C51 C52 1.405(14) . ?
C51 H51 0.9300 . ?
C52 C53 1.347(13) . ?
C52 H52 0.9300 . ?
C53 C54 1.365(11) . ?
C53 H53 0.9300 . ?
C54 C55 1.410(11) . ?
C54 H54 0.9300 . ?
C55 N5 1.420(9) . ?
C56 O3 1.224(8) . ?
C56 N5 1.412(9) . ?
C56 C57 1.466(10) . ?
C57 C58 1.336(9) . ?
C58 C66 1.426(9) . ?
C58 C59 1.492(11) . ?
C59 O4 1.217(9) . ?
C59 N5 1.391(9) . ?
C60 C61 1.383(9) . ?
C60 C65 1.388(9) . ?
C60 N6 1.394(8) . ?
C61 C62 1.414(10) . ?
C61 H61 0.9300 . ?
C62 C63 1.387(10) . ?
C62 H62 0.9300 . ?
C63 C64 1.388(10) . ?
C63 H63 0.9300 . ?
C64 C65 1.403(9) . ?
C64 H64 0.9300 . ?
C65 C66 1.447(9) . ?
C66 C67 1.377(9) . ?
C67 N6 1.351(7) . ?
C67 C74 1.566(9) . ?
C68 C73 1.380(9) . ?
C68 C69 1.390(10) . ?
C68 H68 0.9300 . ?
C69 C70 1.384(10) . ?
C69 H69 0.9300 . ?
C70 C71 1.348(10) . ?
C70 H70 0.9300 . ?
C71 C72 1.380(10) . ?
C71 H71 0.9300 . ?
C72 C73 1.414(9) . ?
C72 H72 0.9300 . ?
C73 C74 1.538(9) . ?
C74 C75 1.541(9) . ?
C75 C76 1.392(9) . ?
C75 C80 1.392(9) . ?
C76 C77 1.381(9) . ?
C76 H76 0.9300 . ?
C77 C78 1.352(10) . ?
C77 H77 0.9300 . ?
C78 C79 1.412(10) . ?
C78 H78 0.9300 . ?
C79 C80 1.365(9) . ?
C79 H79 0.9300 . ?
C80 H80 0.9300 . ?
C1S Cl1S 1.711(9) . ?
C1S Cl2S 1.714(9) . ?
C1S Cl3S 1.733(9) . ?
C1S H1S 0.9800 . ?
N3 H3A 0.8600 . ?
N6 H6A 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 126.7(8) . . ?
C3 C2 C7 125.0(8) . . ?
N1 C2 C7 108.3(6) . . ?
C4 C3 C2 117.0(8) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 120.7(8) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.2(8) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.5(7) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 115.4(7) . . ?
C6 C7 C8 137.2(7) . . ?
C2 C7 C8 107.4(7) . . ?
C9 C8 C7 106.4(6) . . ?
C9 C8 C34 123.2(6) . . ?
C7 C8 C34 130.0(7) . . ?
N1 C9 C8 110.0(6) . . ?
N1 C9 C17 123.6(7) . . ?
C8 C9 C17 126.2(6) . . ?
C15 C10 C11 122.9(8) . . ?
C15 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 117.0(9) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C11 C12 C13 122.5(9) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C12 C13 C14 118.9(8) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 118.5(8) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C10 C15 C14 120.0(8) . . ?
C10 C15 N2 120.5(7) . . ?
C14 C15 N2 119.4(8) . . ?
O1 C16 N2 124.3(7) . . ?
O1 C16 C17 128.3(7) . . ?
N2 C16 C17 107.4(6) . . ?
C18 C17 C9 127.5(6) . . ?
C18 C17 C16 107.5(6) . . ?
C9 C17 C16 124.4(6) . . ?
C17 C18 C26 125.7(6) . . ?
C17 C18 C19 108.5(6) . . ?
C26 C18 C19 125.6(6) . . ?
O2 C19 N2 124.7(6) . . ?
O2 C19 C18 128.0(7) . . ?
N2 C19 C18 107.2(6) . . ?
C25 C20 N3 109.4(6) . . ?
C25 C20 C21 123.1(7) . . ?
N3 C20 C21 127.6(7) . . ?
C22 C21 C20 115.9(7) . . ?
C22 C21 H21 122.1 . . ?
C20 C21 H21 122.1 . . ?
C21 C22 C23 122.1(7) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C22 121.2(7) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 117.5(7) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
C20 C25 C24 120.2(6) . . ?
C20 C25 C26 106.7(6) . . ?
C24 C25 C26 133.1(7) . . ?
C27 C26 C18 122.0(6) . . ?
C27 C26 C25 107.0(6) . . ?
C18 C26 C25 130.9(7) . . ?
N3 C27 C26 108.5(5) . . ?
N3 C27 C34 122.6(6) . . ?
C26 C27 C34 128.7(6) . . ?
C33 C28 C29 121.3(8) . . ?
C33 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 121.0(8) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 118.4(9) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
C30 C31 C32 121.8(8) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C33 120.5(7) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C28 C33 C32 116.9(7) . . ?
C28 C33 C34 125.5(7) . . ?
C32 C33 C34 117.4(6) . . ?
C33 C34 C27 111.1(5) . . ?
C33 C34 C8 110.3(6) . . ?
C27 C34 C8 108.4(5) . . ?
C33 C34 C35 111.0(5) . . ?
C27 C34 C35 106.4(5) . . ?
C8 C34 C35 109.4(5) . . ?
C40 C35 C36 117.5(6) . . ?
C40 C35 C34 120.7(6) . . ?
C36 C35 C34 121.8(5) . . ?
C35 C36 C37 121.3(6) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C38 C37 C36 119.4(7) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C39 120.6(7) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C40 119.1(7) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C35 C40 C39 122.0(7) . . ?
C35 C40 H40 119.0 . . ?
C39 C40 H40 119.0 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 N4 127.0(7) . . ?
C43 C42 C47 124.6(7) . . ?
N4 C42 C47 108.4(6) . . ?
C44 C43 C42 116.6(7) . . ?
C44 C43 H43 121.7 . . ?
C42 C43 H43 121.7 . . ?
C43 C44 C45 120.7(8) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 122.7(8) . . ?
C44 C45 H45 118.7 . . ?
C46 C45 H45 118.7 . . ?
C45 C46 C47 118.5(7) . . ?
C45 C46 H46 120.7 . . ?
C47 C46 H46 120.7 . . ?
C46 C47 C42 116.5(7) . . ?
C46 C47 C48 135.3(7) . . ?
C42 C47 C48 107.7(6) . . ?
C49 C48 C47 105.8(6) . . ?
C49 C48 C74 122.6(6) . . ?
C47 C48 C74 131.5(6) . . ?
N4 C49 C48 110.4(6) . . ?
N4 C49 C57 123.8(6) . . ?
C48 C49 C57 125.6(6) . . ?
C55 C50 C51 118.7(9) . . ?
C55 C50 H50 120.7 . . ?
C51 C50 H50 120.7 . . ?
C50 C51 C52 120.2(10) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
C53 C52 C51 119.7(11) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 121.9(11) . . ?
C52 C53 H53 119.0 . . ?
C54 C53 H53 119.0 . . ?
C53 C54 C55 118.9(9) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
C50 C55 C54 120.5(8) . . ?
C50 C55 N5 119.6(8) . . ?
C54 C55 N5 119.8(8) . . ?
O3 C56 N5 122.0(7) . . ?
O3 C56 C57 131.3(7) . . ?
N5 C56 C57 106.6(7) . . ?
C58 C57 C56 109.8(7) . . ?
C58 C57 C49 125.9(7) . . ?
C56 C57 C49 123.9(6) . . ?
C57 C58 C66 127.5(7) . . ?
C57 C58 C59 107.4(7) . . ?
C66 C58 C59 125.0(7) . . ?
O4 C59 N5 125.4(8) . . ?
O4 C59 C58 127.1(8) . . ?
N5 C59 C58 107.4(8) . . ?
C61 C60 C65 124.6(7) . . ?
C61 C60 N6 127.7(7) . . ?
C65 C60 N6 107.7(6) . . ?
C60 C61 C62 115.9(7) . . ?
C60 C61 H61 122.1 . . ?
C62 C61 H61 122.1 . . ?
C63 C62 C61 120.4(7) . . ?
C63 C62 H62 119.8 . . ?
C61 C62 H62 119.8 . . ?
C62 C63 C64 122.5(8) . . ?
C62 C63 H63 118.8 . . ?
C64 C63 H63 118.8 . . ?
C63 C64 C65 118.0(7) . . ?
C63 C64 H64 121.0 . . ?
C65 C64 H64 121.0 . . ?
C60 C65 C64 118.7(7) . . ?
C60 C65 C66 107.3(6) . . ?
C64 C65 C66 134.0(7) . . ?
C67 C66 C58 122.8(6) . . ?
C67 C66 C65 105.5(6) . . ?
C58 C66 C65 131.7(6) . . ?
N6 C67 C66 110.7(6) . . ?
N6 C67 C74 122.1(6) . . ?
C66 C67 C74 126.7(6) . . ?
C73 C68 C69 122.5(7) . . ?
C73 C68 H68 118.8 . . ?
C69 C68 H68 118.8 . . ?
C70 C69 C68 118.1(8) . . ?
C70 C69 H69 120.9 . . ?
C68 C69 H69 120.9 . . ?
C71 C70 C69 120.7(8) . . ?
C71 C70 H70 119.7 . . ?
C69 C70 H70 119.7 . . ?
C70 C71 C72 121.8(8) . . ?
C70 C71 H71 119.1 . . ?
C72 C71 H71 119.1 . . ?
C71 C72 C73 119.4(7) . . ?
C71 C72 H72 120.3 . . ?
C73 C72 H72 120.3 . . ?
C68 C73 C72 117.5(7) . . ?
C68 C73 C74 123.7(6) . . ?
C72 C73 C74 118.8(7) . . ?
C48 C74 C73 110.3(5) . . ?
C48 C74 C75 111.8(6) . . ?
C73 C74 C75 111.1(5) . . ?
C48 C74 C67 108.2(5) . . ?
C73 C74 C67 107.9(6) . . ?
C75 C74 C67 107.4(5) . . ?
C76 C75 C80 117.7(6) . . ?
C76 C75 C74 121.3(6) . . ?
C80 C75 C74 121.0(6) . . ?
C77 C76 C75 120.7(7) . . ?
C77 C76 H76 119.6 . . ?
C75 C76 H76 119.6 . . ?
C78 C77 C76 120.5(8) . . ?
C78 C77 H77 119.7 . . ?
C76 C77 H77 119.7 . . ?
C77 C78 C79 120.4(7) . . ?
C77 C78 H78 119.8 . . ?
C79 C78 H78 119.8 . . ?
C80 C79 C78 118.3(8) . . ?
C80 C79 H79 120.8 . . ?
C78 C79 H79 120.8 . . ?
C79 C80 C75 122.2(7) . . ?
C79 C80 H80 118.9 . . ?
C75 C80 H80 118.9 . . ?
Cl1S C1S Cl2S 112.3(5) . . ?
Cl1S C1S Cl3S 109.9(5) . . ?
Cl2S C1S Cl3S 110.3(5) . . ?
Cl1S C1S H1S 108.1 . . ?
Cl2S C1S H1S 108.1 . . ?
Cl3S C1S H1S 108.1 . . ?
C9 N1 C2 107.7(6) . . ?
C9 N1 C1 128.6(7) . . ?
C2 N1 C1 123.1(6) . . ?
C16 N2 C19 109.3(6) . . ?
C16 N2 C15 124.5(6) . . ?
C19 N2 C15 126.2(6) . . ?
C27 N3 C20 108.5(5) . . ?
C27 N3 H3A 125.8 . . ?
C20 N3 H3A 125.8 . . ?
C49 N4 C42 107.6(6) . . ?
C49 N4 C41 128.7(6) . . ?
C42 N4 C41 123.3(6) . . ?
C59 N5 C56 108.7(7) . . ?
C59 N5 C55 124.7(7) . . ?
C56 N5 C55 126.3(7) . . ?
C67 N6 C60 108.6(5) . . ?
C67 N6 H6A 125.7 . . ?
C60 N6 H6A 125.7 . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2177754'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H29 N3 O2'
_chemical_formula_sum            'C41 H29 N3 O2'
_chemical_formula_weight         595.67

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

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

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

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

_cell_length_a                   11.3215(4)
_cell_length_b                   12.4187(5)
_cell_length_c                   13.2902(5)
_cell_angle_alpha                114.1368(12)
_cell_angle_beta                 110.5982(12)
_cell_angle_gamma                97.3589(13)
_cell_volume                     1513.15(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.01

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            21473
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5890
_reflns_number_gt                4430
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0575P)²+0.3746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5890
_refine_ls_number_parameters     462
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.07388(17) 0.21569(17) 0.21208(17) 0.0478(4) Uani 1 1 d . . . . .
H1A H 1.0407 0.1379 0.2075 0.072 Uiso 1 1 calc R U . . .
H1B H 1.0972 0.2828 0.2924 0.072 Uiso 1 1 calc R U . . .
H1C H 1.1512 0.2171 0.1976 0.072 Uiso 1 1 calc R U . . .
C2 C 0.96859(15) 0.20587(14) 0.00796(14) 0.0364(4) Uani 1 1 d . . . . .
C3 C 1.03757(17) 0.13865(16) -0.04922(16) 0.0446(4) Uani 1 1 d . . . . .
H3 H 1.0947 0.1041 -0.0121 0.053 Uiso 1 1 calc R U . . .
C4 C 1.01827(18) 0.12539(17) -0.16146(17) 0.0486(5) Uani 1 1 d . . . . .
H4 H 1.0640 0.0820 -0.2010 0.058 Uiso 1 1 calc R U . . .
C5 C 0.93154(18) 0.17550(16) -0.21783(16) 0.0476(4) Uani 1 1 d . . . . .
H5 H 0.9199 0.1643 -0.2947 0.057 Uiso 1 1 calc R U . . .
C6 C 0.86232(17) 0.24140(15) -0.16243(15) 0.0414(4) Uani 1 1 d . . . . .
H6 H 0.8031 0.2726 -0.2023 0.050 Uiso 1 1 calc R U . . .
C7 C 0.88236(15) 0.26085(14) -0.04468(14) 0.0341(4) Uani 1 1 d . . . . .
C8 C 0.83391(14) 0.32368(14) 0.04278(13) 0.0323(3) Uani 1 1 d . . . . .
C9 C 0.88888(15) 0.30080(14) 0.13969(14) 0.0336(3) Uani 1 1 d . . . . .
C10 C 0.5973(4) 0.1444(4) 0.4639(4) 0.0767(11) Uani 0.675(4) 1 d . U P A 1
H10 H 0.6583 0.1385 0.5284 0.092 Uiso 0.675(4) 1 calc R U P A 1
C11 C 0.4619(5) 0.0862(5) 0.4165(5) 0.0893(12) Uani 0.675(4) 1 d . U P A 1
H11 H 0.4327 0.0470 0.4539 0.107 Uiso 0.675(4) 1 calc R U P A 1
C12 C 0.3685(10) 0.0856(8) 0.3133(6) 0.0808(13) Uani 0.675(4) 1 d . U P A 1
H12 H 0.2789 0.0402 0.2766 0.097 Uiso 0.675(4) 1 calc R U P A 1
C13 C 0.4130(3) 0.1521(4) 0.2702(4) 0.0707(9) Uani 0.675(4) 1 d . U P A 1
H13 H 0.3523 0.1593 0.2065 0.085 Uiso 0.675(4) 1 calc R U P A 1
C14 C 0.5462(3) 0.2108(4) 0.3167(4) 0.0623(8) Uani 0.675(4) 1 d . U P A 1
H14 H 0.5739 0.2525 0.2806 0.075 Uiso 0.675(4) 1 calc R U P A 1
C10' C 0.5885(10) 0.0965(9) 0.4059(9) 0.0709(16) Uani 0.325(4) 1 d . U P A 2
H10' H 0.6475 0.0578 0.4334 0.085 Uiso 0.325(4) 1 calc R U P A 2
C11' C 0.4530(10) 0.0375(10) 0.3569(9) 0.0797(16) Uani 0.325(4) 1 d . U P A 2
H11' H 0.4195 -0.0450 0.3363 0.096 Uiso 0.325(4) 1 calc R U P A 2
C12' C 0.373(2) 0.1067(18) 0.3410(14) 0.0836(18) Uani 0.325(4) 1 d . U P A 2
H12' H 0.2853 0.0784 0.3262 0.100 Uiso 0.325(4) 1 calc R U P A 2
C13' C 0.4172(8) 0.2170(9) 0.3460(9) 0.0884(16) Uani 0.325(4) 1 d . U P A 2
H13' H 0.3568 0.2555 0.3205 0.106 Uiso 0.325(4) 1 calc R U P A 2
C14' C 0.5519(7) 0.2719(9) 0.3890(9) 0.0767(16) Uani 0.325(4) 1 d . U P A 2
H14' H 0.5827 0.3507 0.3995 0.092 Uiso 0.325(4) 1 calc R U P A 2
C15 C 0.64042(19) 0.20945(18) 0.41622(17) 0.0503(4) Uani 1 1 d . U . . .
C16 C 0.78759(19) 0.27253(19) 0.47041(17) 0.0516(5) Uani 1 1 d . . . . .
H16A H 0.8176 0.3399 0.5534 0.062 Uiso 1 1 calc R U . . .
H16B H 0.8339 0.2132 0.4760 0.062 Uiso 1 1 calc R U . . .
C17 C 0.84482(16) 0.25311(16) 0.29825(15) 0.0387(4) Uani 1 1 d . . . . .
C18 C 0.86200(15) 0.33469(14) 0.24490(14) 0.0338(4) Uani 1 1 d . . . . .
C19 C 0.83669(15) 0.44051(14) 0.30467(13) 0.0343(4) Uani 1 1 d . . . . .
C20 C 0.81662(17) 0.43620(16) 0.40893(15) 0.0416(4) Uani 1 1 d . . . . .
C21 C 0.78426(15) 0.70748(14) 0.26017(14) 0.0356(4) Uani 1 1 d . . . . .
C22 C 0.77894(18) 0.82841(16) 0.29737(17) 0.0464(4) Uani 1 1 d . . . . .
H22 H 0.7478 0.8565 0.2411 0.056 Uiso 1 1 calc R U . . .
C23 C 0.8219(2) 0.90402(17) 0.42129(18) 0.0583(5) Uani 1 1 d . . . . .
H23 H 0.8208 0.9857 0.4498 0.070 Uiso 1 1 calc R U . . .
C24 C 0.8669(2) 0.86170(17) 0.50460(18) 0.0598(5) Uani 1 1 d . . . . .
H24 H 0.8952 0.9155 0.5879 0.072 Uiso 1 1 calc R U . . .
C25 C 0.87064(18) 0.74231(16) 0.46733(15) 0.0473(4) Uani 1 1 d . . . . .
H25 H 0.9015 0.7153 0.5246 0.057 Uiso 1 1 calc R U . . .
C26 C 0.82734(15) 0.66162(14) 0.34199(14) 0.0350(4) Uani 1 1 d . . . . .
C27 C 0.81828(15) 0.53402(14) 0.26945(13) 0.0330(3) Uani 1 1 d . . . . .
C28 C 0.77087(14) 0.50915(14) 0.14782(14) 0.0323(3) Uani 1 1 d . . . . .
C29 C 0.72376(14) 0.38480(14) 0.02972(13) 0.0317(3) Uani 1 1 d . . . . .
C30 C 0.69422(15) 0.40959(14) -0.07958(14) 0.0342(4) Uani 1 1 d . . . . .
C31 C 0.79486(18) 0.48931(15) -0.07756(15) 0.0423(4) Uani 1 1 d . . . . .
H31 H 0.8773 0.5299 -0.0086 0.051 Uiso 1 1 calc R U . . .
C32 C 0.7735(2) 0.50858(17) -0.17661(17) 0.0539(5) Uani 1 1 d . . . . .
H32 H 0.8420 0.5609 -0.1745 0.065 Uiso 1 1 calc R U . . .
C33 C 0.6518(2) 0.4512(2) -0.27852(18) 0.0632(6) Uani 1 1 d . . . . .
H33 H 0.6380 0.4639 -0.3455 0.076 Uiso 1 1 calc R U . . .
C34 C 0.5507(2) 0.3747(2) -0.28075(18) 0.0623(5) Uani 1 1 d . . . . .
H34 H 0.4676 0.3369 -0.3489 0.075 Uiso 1 1 calc R U . . .
C35 C 0.57159(17) 0.35350(17) -0.18231(15) 0.0454(4) Uani 1 1 d . . . . .
H35 H 0.5025 0.3010 -0.1852 0.054 Uiso 1 1 calc R U . . .
C36 C 0.59949(15) 0.29760(14) 0.01267(13) 0.0327(3) Uani 1 1 d . . . . .
C37 C 0.51780(16) 0.34275(16) 0.06486(15) 0.0410(4) Uani 1 1 d . . . . .
H37 H 0.5369 0.4282 0.1114 0.049 Uiso 1 1 calc R U . . .
C38 C 0.40770(18) 0.26146(19) 0.04826(18) 0.0515(5) Uani 1 1 d . . . . .
H38 H 0.3538 0.2928 0.0842 0.062 Uiso 1 1 calc R U . . .
C39 C 0.37750(18) 0.13480(19) -0.02099(19) 0.0527(5) Uani 1 1 d . . . . .
H39 H 0.3039 0.0807 -0.0314 0.063 Uiso 1 1 calc R U . . .
C40 C 0.45647(18) 0.08900(17) -0.07453(18) 0.0504(5) Uani 1 1 d . . . . .
H40 H 0.4359 0.0036 -0.1224 0.060 Uiso 1 1 calc R U . . .
C41 C 0.56663(17) 0.16962(15) -0.05747(16) 0.0437(4) Uani 1 1 d . . . . .
H41 H 0.6200 0.1375 -0.0937 0.052 Uiso 1 1 calc R U . . .
N1 N 0.97168(13) 0.22980(12) 0.11931(12) 0.0372(3) Uani 1 1 d . . . . .
N2 N 0.82348(14) 0.32240(13) 0.39935(13) 0.0437(3) Uani 1 1 d . . . . .
N3 N 0.74970(13) 0.61285(11) 0.14360(12) 0.0364(3) Uani 1 1 d . . . . .
H3A H 0.7191 0.6186 0.0775 0.044 Uiso 1 1 calc R U . . .
O1 O 0.84426(12) 0.14646(11) 0.26326(11) 0.0500(3) Uani 1 1 d . . . . .
O2 O 0.79589(15) 0.51268(12) 0.48716(12) 0.0614(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.454(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.371(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.411(2) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.441(2) . ?
C8 C9 1.381(2) . ?
C8 C29 1.536(2) . ?
C9 N1 1.3873(19) . ?
C9 C18 1.441(2) . ?
C10 C15 1.351(4) . ?
C10 C11 1.391(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.322(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C10' C15 1.381(9) . ?
C10' C11' 1.391(12) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.35(3) . ?
C11' H11' 0.9300 . ?
C12' C13' 1.36(2) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.385(11) . ?
C13' H13' 0.9300 . ?
C14' C15 1.382(8) . ?
C14' H14' 0.9300 . ?
C15 C16 1.506(3) . ?
C16 N2 1.457(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.2094(19) . ?
C17 N2 1.393(2) . ?
C17 C18 1.484(2) . ?
C18 C19 1.358(2) . ?
C19 C27 1.431(2) . ?
C19 C20 1.501(2) . ?
C20 O2 1.208(2) . ?
C20 N2 1.381(2) . ?
C21 N3 1.3788(19) . ?
C21 C22 1.393(2) . ?
C21 C26 1.396(2) . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.446(2) . ?
C27 C28 1.391(2) . ?
C28 N3 1.3593(19) . ?
C28 C29 1.533(2) . ?
C29 C30 1.539(2) . ?
C29 C36 1.545(2) . ?
C30 C35 1.385(2) . ?
C30 C31 1.395(2) . ?
C31 C32 1.377(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.373(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.384(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.385(2) . ?
C36 C41 1.388(2) . ?
C37 C38 1.387(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.377(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.370(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.380(2) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
N3 H3A 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 127.70(15) . . ?
N1 C2 C7 109.44(13) . . ?
C3 C2 C7 122.86(15) . . ?
C4 C3 C2 117.67(16) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.21(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.55(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.21(16) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 117.43(14) . . ?
C6 C7 C8 136.46(15) . . ?
C2 C7 C8 106.09(13) . . ?
C9 C8 C7 106.64(13) . . ?
C9 C8 C29 122.44(13) . . ?
C7 C8 C29 130.02(13) . . ?
C8 C9 N1 110.05(13) . . ?
C8 C9 C18 127.81(14) . . ?
N1 C9 C18 122.01(14) . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 121.1(6) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 117.3(8) . . ?
C13 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
C12 C13 C14 121.9(5) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C15 C10' C11' 123.7(8) . . ?
C15 C10' H10' 118.2 . . ?
C11' C10' H10' 118.2 . . ?
C12' C11' C10' 116.1(13) . . ?
C12' C11' H11' 122.0 . . ?
C10' C11' H11' 122.0 . . ?
C11' C12' C13' 122(2) . . ?
C11' C12' H12' 119.1 . . ?
C13' C12' H12' 119.1 . . ?
C12' C13' C14' 120.2(12) . . ?
C12' C13' H13' 119.9 . . ?
C14' C13' H13' 119.9 . . ?
C15 C14' C13' 119.9(7) . . ?
C15 C14' H14' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C10' C15 C14' 116.7(6) . . ?
C10 C15 C14 117.7(3) . . ?
C10 C15 C16 118.8(2) . . ?
C10' C15 C16 123.0(4) . . ?
C14' C15 C16 119.8(4) . . ?
C14 C15 C16 123.42(19) . . ?
N2 C16 C15 113.63(15) . . ?
N2 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
N2 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
O1 C17 N2 124.26(16) . . ?
O1 C17 C18 129.47(16) . . ?
N2 C17 C18 106.23(14) . . ?
C19 C18 C9 126.21(14) . . ?
C19 C18 C17 108.61(14) . . ?
C9 C18 C17 124.94(14) . . ?
C18 C19 C27 127.28(14) . . ?
C18 C19 C20 107.35(14) . . ?
C27 C19 C20 125.08(14) . . ?
O2 C20 N2 124.02(16) . . ?
O2 C20 C19 129.41(16) . . ?
N2 C20 C19 106.56(13) . . ?
N3 C21 C22 129.32(16) . . ?
N3 C21 C26 107.66(13) . . ?
C22 C21 C26 123.02(15) . . ?
C23 C22 C21 116.65(17) . . ?
C23 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C22 C23 C24 121.58(17) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 121.51(17) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 119.03(17) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C21 C26 C25 118.19(15) . . ?
C21 C26 C27 106.71(13) . . ?
C25 C26 C27 135.07(16) . . ?
C28 C27 C19 122.95(14) . . ?
C28 C27 C26 106.77(13) . . ?
C19 C27 C26 129.91(14) . . ?
N3 C28 C27 108.43(13) . . ?
N3 C28 C29 121.34(13) . . ?
C27 C28 C29 129.42(14) . . ?
C28 C29 C8 109.16(12) . . ?
C28 C29 C30 108.82(12) . . ?
C8 C29 C30 109.77(12) . . ?
C28 C29 C36 108.93(12) . . ?
C8 C29 C36 108.27(12) . . ?
C30 C29 C36 111.85(12) . . ?
C35 C30 C31 118.09(15) . . ?
C35 C30 C29 122.53(14) . . ?
C31 C30 C29 119.36(14) . . ?
C32 C31 C30 120.71(16) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C31 120.55(18) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.45(18) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C35 120.47(18) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C34 C35 C30 120.69(17) . . ?
C34 C35 H35 119.7 . . ?
C30 C35 H35 119.7 . . ?
C37 C36 C41 118.03(15) . . ?
C37 C36 C29 122.14(14) . . ?
C41 C36 C29 119.82(14) . . ?
C36 C37 C38 120.45(16) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 120.52(17) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C38 119.60(17) . . ?
C40 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
C39 C40 C41 120.01(17) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C40 C41 C36 121.38(16) . . ?
C40 C41 H41 119.3 . . ?
C36 C41 H41 119.3 . . ?
C2 N1 C9 107.76(13) . . ?
C2 N1 C1 123.76(13) . . ?
C9 N1 C1 125.99(13) . . ?
C20 N2 C17 110.84(14) . . ?
C20 N2 C16 123.99(14) . . ?
C17 N2 C16 124.17(15) . . ?
C28 N3 C21 110.42(13) . . ?
C28 N3 H3A 124.8 . . ?
C21 N3 H3A 124.8 . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_9a
_database_code_depnum_ccdc_archive 'CCDC 2177761'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 N3 O4, C H Cl3'
_chemical_formula_sum            'C32 H20 Cl3 N3 O4'
_chemical_formula_weight         616.86

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'
Cl Cl 0.1484 0.1585 '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                   12.0107(18)
_cell_length_b                   12.0920(19)
_cell_length_c                   12.2492(18)
_cell_angle_alpha                118.132(4)
_cell_angle_beta                 96.981(4)
_cell_angle_gamma                111.445(4)
_cell_volume                     1363.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7080
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.92

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.382
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5736
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            15501
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5270
_reflns_number_gt                3692
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1094P)²+3.3783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5270
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2536
_refine_ls_wR_factor_gt          0.2283
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7854(5) 0.1306(5) 0.2608(5) 0.0486(12) Uani 1 1 d . . . . .
H1A H 0.7219 0.0484 0.1765 0.073 Uiso 1 1 calc R U . . .
H1B H 0.7560 0.1315 0.3305 0.073 Uiso 1 1 calc R U . . .
H1C H 0.8640 0.1265 0.2712 0.073 Uiso 1 1 calc R U . . .
C2 C 0.8226(4) 0.3809(5) 0.3824(4) 0.0354(9) Uani 1 1 d . . . . .
C3 C 0.8505(4) 0.4123(6) 0.5108(5) 0.0461(11) Uani 1 1 d . . . . .
H3 H 0.8572 0.3476 0.5284 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8676(5) 0.5411(6) 0.6096(5) 0.0530(13) Uani 1 1 d . . . . .
H4 H 0.8870 0.5652 0.6962 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8565(5) 0.6370(5) 0.5828(5) 0.0493(12) Uani 1 1 d . . . . .
H5 H 0.8692 0.7244 0.6521 0.059 Uiso 1 1 calc R U . . .
C6 C 0.8273(4) 0.6055(5) 0.4564(4) 0.0407(10) Uani 1 1 d . . . . .
H6 H 0.8200 0.6707 0.4401 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8084(4) 0.4733(4) 0.3517(4) 0.0342(9) Uani 1 1 d . . . . .
C8 C 0.7842(4) 0.4067(4) 0.2115(4) 0.0319(9) Uani 1 1 d . . . . .
C9 C 0.7911(4) 0.2807(4) 0.1655(4) 0.0319(9) Uani 1 1 d . . . . .
C10 C 0.6953(4) 0.5517(5) 0.1634(4) 0.0394(10) Uani 1 1 d . . . . .
C11 C 0.7557(4) 0.4566(4) 0.1321(4) 0.0342(9) Uani 1 1 d . . . . .
C12 C 0.7747(4) 0.4293(4) 0.0168(4) 0.0347(9) Uani 1 1 d . . . . .
C13 C 0.7432(4) 0.5171(5) -0.0202(4) 0.0408(10) Uani 1 1 d . . . . .
C14 C 0.6481(6) 0.6802(6) 0.0681(6) 0.0576(13) Uani 1 1 d . . . . .
H14A H 0.7206 0.7718 0.1039 0.086 Uiso 1 1 calc R U . . .
H14B H 0.5954 0.6911 0.1212 0.086 Uiso 1 1 calc R U . . .
H14C H 0.5991 0.6416 -0.0212 0.086 Uiso 1 1 calc R U . . .
C15 C 0.9205(4) 0.2638(4) -0.1983(4) 0.0366(10) Uani 1 1 d . . . . .
C16 C 0.9772(4) 0.2445(5) -0.2949(5) 0.0436(11) Uani 1 1 d . . . . .
H16 H 0.9867 0.2972 -0.3323 0.052 Uiso 1 1 calc R U . . .
C17 C 1.0180(5) 0.1445(5) -0.3317(5) 0.0475(12) Uani 1 1 d . . . . .
H17 H 1.0551 0.1278 -0.3962 0.057 Uiso 1 1 calc R U . . .
C18 C 1.0042(5) 0.0671(5) -0.2734(5) 0.0496(12) Uani 1 1 d . . . . .
H18 H 1.0330 0.0001 -0.3002 0.060 Uiso 1 1 calc R U . . .
C19 C 0.9495(4) 0.0867(5) -0.1775(5) 0.0420(10) Uani 1 1 d . . . . .
H19 H 0.9431 0.0347 -0.1396 0.050 Uiso 1 1 calc R U . . .
C20 C 0.9036(4) 0.1860(4) -0.1377(4) 0.0331(9) Uani 1 1 d . . . . .
C21 C 0.8406(4) 0.2371(4) -0.0459(4) 0.0307(9) Uani 1 1 d . . . . .
C22 C 0.8260(4) 0.3415(4) -0.0543(4) 0.0327(9) Uani 1 1 d . . . . .
C23 C 0.7776(4) 0.1716(4) 0.0262(4) 0.0300(8) Uani 1 1 d . . . . .
C24 C 0.6336(4) 0.0618(4) -0.0643(4) 0.0324(9) Uani 1 1 d . . . . .
C25 C 0.6218(4) -0.0811(4) -0.1345(4) 0.0336(9) Uani 1 1 d . . . . .
C26 C 0.5160(4) -0.2112(5) -0.2368(5) 0.0449(11) Uani 1 1 d . . . . .
H26 H 0.4395 -0.2152 -0.2690 0.054 Uiso 1 1 calc R U . . .
C27 C 0.5279(5) -0.3328(5) -0.2885(5) 0.0520(12) Uani 1 1 d . . . . .
H27 H 0.4586 -0.4202 -0.3572 0.062 Uiso 1 1 calc R U . . .
C28 C 0.6419(5) -0.3277(5) -0.2399(5) 0.0484(12) Uani 1 1 d . . . . .
H28 H 0.6477 -0.4116 -0.2772 0.058 Uiso 1 1 calc R U . . .
C29 C 0.7467(5) -0.1998(5) -0.1370(5) 0.0418(10) Uani 1 1 d . . . . .
H29 H 0.8223 -0.1967 -0.1033 0.050 Uiso 1 1 calc R U . . .
C30 C 0.7352(4) -0.0770(4) -0.0860(4) 0.0317(9) Uani 1 1 d . . . . .
C31 C 0.8324(4) 0.0719(4) 0.0200(4) 0.0315(9) Uani 1 1 d . . . . .
C32 C 0.5412(6) 0.7977(8) 0.3933(7) 0.0767(18) Uani 1 1 d . . . . .
H32 H 0.5499 0.7141 0.3345 0.092 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5006(2) 0.8587(2) 0.2990(2) 0.1060(7) Uani 1 1 d . . . . .
Cl2 Cl 0.4143(2) 0.7378(2) 0.4442(2) 0.1063(7) Uani 1 1 d . . . . .
Cl3 Cl 0.6833(3) 0.9196(4) 0.5195(4) 0.1968(19) Uani 1 1 d . . . . .
N1 N 0.8071(3) 0.2608(4) 0.2669(3) 0.0339(8) Uani 1 1 d . . . . .
N2 N 0.6920(4) 0.5838(4) 0.0684(4) 0.0436(9) Uani 1 1 d . . . . .
N3 N 0.8730(4) 0.3553(4) -0.1464(3) 0.0387(8) Uani 1 1 d . . . . .
H3A H 0.8724 0.4132 -0.1681 0.046 Uiso 1 1 calc R U . . .
O1 O 0.6512(3) 0.5908(4) 0.2487(3) 0.0525(9) Uani 1 1 d . . . . .
O2 O 0.7584(4) 0.5319(4) -0.1099(3) 0.0572(9) Uani 1 1 d . . . . .
O3 O 0.9388(3) 0.1130(3) 0.0880(3) 0.0432(8) Uani 1 1 d . . . . .
O4 O 0.5502(3) 0.0940(4) -0.0703(3) 0.0475(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.461(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.392(6) . ?
C2 N1 1.395(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.365(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.444(6) . ?
C8 C9 1.393(6) . ?
C8 C11 1.431(6) . ?
C9 N1 1.378(5) . ?
C9 C23 1.527(6) . ?
C10 O1 1.204(5) . ?
C10 N2 1.390(6) . ?
C10 C11 1.502(6) . ?
C11 C12 1.360(6) . ?
C12 C22 1.415(6) . ?
C12 C13 1.477(6) . ?
C13 O2 1.217(5) . ?
C13 N2 1.381(6) . ?
C14 N2 1.446(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.357(6) . ?
C15 C16 1.404(6) . ?
C15 C20 1.427(6) . ?
C16 C17 1.370(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.407(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.453(6) . ?
C21 C22 1.385(6) . ?
C21 C23 1.537(6) . ?
C22 N3 1.373(5) . ?
C23 C31 1.549(5) . ?
C23 C24 1.565(5) . ?
C24 O4 1.206(5) . ?
C24 C25 1.461(6) . ?
C25 C30 1.391(6) . ?
C25 C26 1.397(6) . ?
C26 C27 1.372(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.393(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.477(6) . ?
C31 O3 1.208(5) . ?
C32 Cl3 1.688(7) . ?
C32 Cl1 1.745(7) . ?
C32 Cl2 1.756(7) . ?
C32 H32 0.9800 . ?
N3 H3A 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 N1 108.8(4) . . ?
C7 C2 C3 122.8(4) . . ?
N1 C2 C3 128.4(4) . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.3(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 117.8(4) . . ?
C2 C7 C8 106.7(4) . . ?
C6 C7 C8 135.3(4) . . ?
C9 C8 C11 125.6(4) . . ?
C9 C8 C7 106.8(4) . . ?
C11 C8 C7 127.6(4) . . ?
N1 C9 C8 109.1(3) . . ?
N1 C9 C23 121.9(3) . . ?
C8 C9 C23 129.0(4) . . ?
O1 C10 N2 123.8(4) . . ?
O1 C10 C11 129.1(4) . . ?
N2 C10 C11 107.0(4) . . ?
C12 C11 C8 128.9(4) . . ?
C12 C11 C10 106.5(4) . . ?
C8 C11 C10 124.6(4) . . ?
C11 C12 C22 127.5(4) . . ?
C11 C12 C13 109.0(4) . . ?
C22 C12 C13 123.3(4) . . ?
O2 C13 N2 124.6(4) . . ?
O2 C13 C12 128.5(4) . . ?
N2 C13 C12 106.9(4) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 127.9(4) . . ?
N3 C15 C20 108.2(4) . . ?
C16 C15 C20 123.8(4) . . ?
C17 C16 C15 117.1(4) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 122.4(4) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C15 116.5(4) . . ?
C19 C20 C21 137.5(4) . . ?
C15 C20 C21 106.0(4) . . ?
C22 C21 C20 106.2(3) . . ?
C22 C21 C23 124.8(4) . . ?
C20 C21 C23 128.0(3) . . ?
N3 C22 C21 109.7(4) . . ?
N3 C22 C12 120.4(4) . . ?
C21 C22 C12 129.9(4) . . ?
C9 C23 C21 114.6(3) . . ?
C9 C23 C31 114.4(3) . . ?
C21 C23 C31 105.6(3) . . ?
C9 C23 C24 111.4(3) . . ?
C21 C23 C24 107.8(3) . . ?
C31 C23 C24 101.9(3) . . ?
O4 C24 C25 128.1(4) . . ?
O4 C24 C23 124.3(4) . . ?
C25 C24 C23 107.6(3) . . ?
C30 C25 C26 120.2(4) . . ?
C30 C25 C24 111.0(4) . . ?
C26 C25 C24 128.8(4) . . ?
C27 C26 C25 118.4(4) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C26 C27 C28 121.1(4) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 121.1(4) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 117.8(4) . . ?
C30 C29 H29 121.1 . . ?
C28 C29 H29 121.1 . . ?
C29 C30 C25 121.5(4) . . ?
C29 C30 C31 128.6(4) . . ?
C25 C30 C31 109.9(3) . . ?
O3 C31 C30 127.4(4) . . ?
O3 C31 C23 124.5(4) . . ?
C30 C31 C23 108.0(3) . . ?
Cl3 C32 Cl1 112.6(5) . . ?
Cl3 C32 Cl2 113.5(4) . . ?
Cl1 C32 Cl2 109.4(4) . . ?
Cl3 C32 H32 107.0 . . ?
Cl1 C32 H32 107.0 . . ?
Cl2 C32 H32 107.0 . . ?
C9 N1 C2 108.4(3) . . ?
C9 N1 C1 129.4(4) . . ?
C2 N1 C1 121.0(4) . . ?
C13 N2 C10 110.2(4) . . ?
C13 N2 C14 125.2(4) . . ?
C10 N2 C14 124.5(4) . . ?
C15 N3 C22 109.8(4) . . ?
C15 N3 H3A 125.1 . . ?
C22 N3 H3A 125.1 . . ?

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
N3 H3A O2 0.86 2.27 2.837(5) 123.6 .

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_5d
_database_code_depnum_ccdc_archive 'CCDC 2177755'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H32 N4 O3, C H Cl3'
_chemical_formula_sum            'C36 H33 Cl3 N4 O3'
_chemical_formula_weight         676.01

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'
Cl Cl 0.1484 0.1585 '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                   17.200(4)
_cell_length_b                   9.5522(19)
_cell_length_c                   22.075(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.167(7)
_cell_angle_gamma                90
_cell_volume                     3404.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6875
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      23.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            26286
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6002
_reflns_number_gt                3537
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.2000P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6002
_refine_ls_number_parameters     419
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1592
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.3344
_refine_ls_wR_factor_gt          0.3019
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5339(4) 0.9966(8) 1.1424(3) 0.086(2) Uani 1 1 d . . . . .
H1A H 0.5610 0.9297 1.1754 0.130 Uiso 1 1 calc R U . . .
H1B H 0.5096 1.0689 1.1603 0.130 Uiso 1 1 calc R U . . .
H1C H 0.5736 1.0372 1.1259 0.130 Uiso 1 1 calc R U . . .
C2 C 0.4180(3) 0.9932(5) 1.0336(3) 0.0494(12) Uani 1 1 d . . . . .
C3 C 0.4185(4) 1.1296(6) 1.0150(4) 0.0748(18) Uani 1 1 d . . . . .
H3 H 0.4550 1.1952 1.0408 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3611(5) 1.1640(6) 0.9551(4) 0.089(2) Uani 1 1 d . . . . .
H4 H 0.3603 1.2547 0.9396 0.107 Uiso 1 1 calc R U . . .
C5 C 0.3055(4) 1.0676(7) 0.9183(3) 0.0803(19) Uani 1 1 d . . . . .
H5 H 0.2658 1.0964 0.8798 0.096 Uiso 1 1 calc R U . . .
C6 C 0.3066(3) 0.9286(6) 0.9369(3) 0.0606(14) Uani 1 1 d . . . . .
H6 H 0.2701 0.8636 0.9106 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3647(3) 0.8892(5) 0.9969(3) 0.0505(12) Uani 1 1 d . . . . .
C8 C 0.3838(3) 0.7603(5) 1.0312(2) 0.0438(11) Uani 1 1 d . . . . .
C9 C 0.4475(3) 0.7888(5) 1.0881(3) 0.0539(13) Uani 1 1 d . . . . .
H9 H 0.4719 0.7237 1.1204 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3794(3) 0.5127(5) 1.0625(2) 0.0456(12) Uani 1 1 d . . . . .
C11 C 0.3384(2) 0.6246(4) 1.0125(2) 0.0408(11) Uani 1 1 d . . . . .
C12 C 0.2469(3) 0.6292(5) 1.0120(2) 0.0474(12) Uani 1 1 d . . . . .
H12 H 0.2281 0.7260 1.0119 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2519(3) 0.5566(6) 1.0731(2) 0.0548(13) Uani 1 1 d . . . . .
C14 C 0.3462(4) 0.3701(8) 1.1453(3) 0.093(2) Uani 1 1 d . . . . .
H14A H 0.3387 0.2793 1.1254 0.139 Uiso 1 1 calc R U . . .
H14B H 0.3101 0.3797 1.1699 0.139 Uiso 1 1 calc R U . . .
H14C H 0.4027 0.3803 1.1733 0.139 Uiso 1 1 calc R U . . .
C15 C 0.3280(3) 0.4790(5) 0.8541(2) 0.0449(11) Uani 1 1 d . . . . .
C16 C 0.3529(4) 0.4285(6) 0.8053(3) 0.0646(15) Uani 1 1 d . . . . .
H16 H 0.4070 0.4401 0.8062 0.078 Uiso 1 1 calc R U . . .
C17 C 0.2945(4) 0.3603(8) 0.7552(3) 0.0804(19) Uani 1 1 d . . . . .
H17 H 0.3097 0.3238 0.7219 0.096 Uiso 1 1 calc R U . . .
C18 C 0.2129(4) 0.3444(7) 0.7531(3) 0.0768(18) Uani 1 1 d . . . . .
H18 H 0.1754 0.2964 0.7188 0.092 Uiso 1 1 calc R U . . .
C19 C 0.1866(3) 0.3982(6) 0.8009(2) 0.0584(14) Uani 1 1 d . . . . .
H19 H 0.1318 0.3896 0.7986 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2454(3) 0.4659(5) 0.8527(2) 0.0447(11) Uani 1 1 d . . . . .
C21 C 0.2453(2) 0.5271(4) 0.9126(2) 0.0409(11) Uani 1 1 d . . . . .
C22 C 0.3240(2) 0.5701(4) 0.9455(2) 0.0390(10) Uani 1 1 d . . . . .
C23 C -0.1851(6) 0.5596(14) 0.7000(5) 0.156(3) Uani 1 1 d . U . . .
H23A H -0.1420 0.5810 0.6831 0.234 Uiso 1 1 calc R U . . .
H23B H -0.2343 0.6105 0.6762 0.234 Uiso 1 1 calc R U . . .
H23C H -0.1965 0.4610 0.6960 0.234 Uiso 1 1 calc R U . . .
C24 C -0.1583(4) 0.6003(10) 0.7687(3) 0.107(2) Uani 1 1 d . U . . .
H24A H -0.1978 0.5632 0.7871 0.128 Uiso 1 1 calc R U . . .
H24B H -0.1600 0.7015 0.7713 0.128 Uiso 1 1 calc R U . . .
C25 C -0.0737(3) 0.5518(9) 0.8091(3) 0.0909(16) Uani 1 1 d . U . . .
H25A H -0.0352 0.5765 0.7873 0.109 Uiso 1 1 calc R U . . .
H25B H -0.0742 0.4506 0.8122 0.109 Uiso 1 1 calc R U . . .
C26 C -0.0417(3) 0.6132(7) 0.8775(3) 0.0704(15) Uani 1 1 d . U . . .
H26A H -0.0426 0.7146 0.8749 0.084 Uiso 1 1 calc R U . . .
H26B H -0.0782 0.5850 0.9004 0.084 Uiso 1 1 calc R U . . .
C27 C 0.1111(3) 0.6381(5) 0.9148(2) 0.0493(12) Uani 1 1 d . . . . .
C28 C 0.1887(2) 0.5464(5) 0.9495(2) 0.0425(11) Uani 1 1 d . . . . .
C29 C 0.1483(2) 0.4127(5) 0.9629(2) 0.0424(11) Uani 1 1 d . . . . .
C30 C 0.1812(3) 0.2884(5) 0.9892(2) 0.0488(12) Uani 1 1 d . . . . .
H30 H 0.2381 0.2746 1.0019 0.059 Uiso 1 1 calc R U . . .
C31 C 0.1307(3) 0.1812(5) 0.9974(2) 0.0534(13) Uani 1 1 d . . . . .
C32 C 0.1652(4) 0.0422(6) 1.0254(3) 0.0801(18) Uani 1 1 d . . . . .
H32A H 0.1761 0.0429 1.0711 0.120 Uiso 1 1 calc R U . . .
H32B H 0.2158 0.0248 1.0174 0.120 Uiso 1 1 calc R U . . .
H32C H 0.1259 -0.0301 1.0057 0.120 Uiso 1 1 calc R U . . .
C33 C 0.0465(3) 0.2054(6) 0.9776(3) 0.0630(15) Uani 1 1 d . . . . .
H33 H 0.0124 0.1350 0.9834 0.076 Uiso 1 1 calc R U . . .
C34 C 0.0111(3) 0.3288(6) 0.9497(3) 0.0597(14) Uani 1 1 d . . . . .
H34 H -0.0459 0.3421 0.9367 0.072 Uiso 1 1 calc R U . . .
C35 C 0.0622(3) 0.4325(5) 0.9414(2) 0.0455(12) Uani 1 1 d . . . . .
N1 N 0.4693(3) 0.9269(5) 1.0902(2) 0.0597(12) Uani 1 1 d . . . . .
N2 N 0.3266(2) 0.4782(5) 1.0953(2) 0.0557(11) Uani 1 1 d . . . . .
N3 N 0.3749(2) 0.5440(4) 0.91126(18) 0.0437(10) Uani 1 1 d . . . . .
H3A H 0.4267 0.5642 0.9229 0.052 Uiso 1 1 calc R U . . .
N4 N 0.0425(2) 0.5662(4) 0.9134(2) 0.0510(10) Uani 1 1 d . . . . .
O1 O 0.44684(19) 0.4605(4) 1.07453(17) 0.0567(9) Uani 1 1 d . . . . .
O2 O 0.2025(2) 0.5556(5) 1.10060(19) 0.0758(12) Uani 1 1 d . . . . .
O3 O 0.1131(2) 0.7541(4) 0.8945(2) 0.0746(12) Uani 1 1 d . . . . .
C36 C 0.5007(4) 0.5117(8) 0.3160(3) 0.094(2) Uani 1 1 d . . . . .
H36 H 0.5357 0.5637 0.3538 0.112 Uiso 1 1 calc R U . . .
Cl1 Cl 0.47432(17) 0.6242(2) 0.24941(12) 0.1252(9) Uani 1 1 d . . . . .
Cl2 Cl 0.40996(16) 0.4629(4) 0.32969(13) 0.1525(12) Uani 1 1 d . . . . .
Cl3 Cl 0.55463(18) 0.3730(3) 0.30587(14) 0.1429(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.456(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.367(8) . ?
C2 C7 1.404(7) . ?
C2 N1 1.408(7) . ?
C3 C4 1.388(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(7) . ?
C8 C9 1.379(7) . ?
C8 C11 1.496(6) . ?
C9 N1 1.368(6) . ?
C9 H9 0.9300 . ?
C10 O1 1.206(5) . ?
C10 N2 1.381(6) . ?
C10 C11 1.524(7) . ?
C11 C22 1.505(6) . ?
C11 C12 1.570(6) . ?
C12 C13 1.492(7) . ?
C12 C28 1.605(6) . ?
C12 H12 0.9800 . ?
C13 O2 1.203(6) . ?
C13 N2 1.421(6) . ?
C14 N2 1.463(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.378(7) . ?
C15 N3 1.388(6) . ?
C15 C20 1.416(6) . ?
C16 C17 1.375(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.446(7) . ?
C21 C22 1.361(6) . ?
C21 C28 1.481(6) . ?
C22 N3 1.363(6) . ?
C23 C24 1.477(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.494(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.534(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N4 1.462(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O3 1.200(6) . ?
C27 N4 1.356(6) . ?
C27 C28 1.559(6) . ?
C28 C29 1.531(6) . ?
C29 C30 1.356(7) . ?
C29 C35 1.403(6) . ?
C30 C31 1.396(7) . ?
C30 H30 0.9300 . ?
C31 C33 1.380(7) . ?
C31 C32 1.497(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.372(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.378(7) . ?
C34 H34 0.9300 . ?
C35 N4 1.409(6) . ?
N3 H3A 0.8600 . ?
C36 Cl3 1.676(8) . ?
C36 Cl1 1.750(8) . ?
C36 Cl2 1.753(7) . ?
C36 H36 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 124.8(6) . . ?
C3 C2 N1 129.0(5) . . ?
C7 C2 N1 106.2(4) . . ?
C2 C3 C4 115.8(6) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 H3 122.1 . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 122.0(6) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 117.8(6) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 117.7(5) . . ?
C2 C7 C8 108.6(4) . . ?
C6 C7 C8 133.7(5) . . ?
C9 C8 C7 106.2(4) . . ?
C9 C8 C11 126.7(4) . . ?
C7 C8 C11 126.8(4) . . ?
N1 C9 C8 110.1(4) . . ?
N1 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
O1 C10 N2 122.8(5) . . ?
O1 C10 C11 128.2(4) . . ?
N2 C10 C11 108.9(4) . . ?
C8 C11 C22 117.6(4) . . ?
C8 C11 C10 109.9(4) . . ?
C22 C11 C10 110.4(4) . . ?
C8 C11 C12 113.9(3) . . ?
C22 C11 C12 100.2(3) . . ?
C10 C11 C12 103.7(4) . . ?
C13 C12 C11 103.6(4) . . ?
C13 C12 C28 111.8(4) . . ?
C11 C12 C28 108.6(4) . . ?
C13 C12 H12 110.9 . . ?
C11 C12 H12 110.9 . . ?
C28 C12 H12 110.9 . . ?
O2 C13 N2 122.2(5) . . ?
O2 C13 C12 129.0(5) . . ?
N2 C13 C12 108.7(4) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N3 128.8(5) . . ?
C16 C15 C20 122.2(5) . . ?
N3 C15 C20 109.0(4) . . ?
C17 C16 C15 117.1(5) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C18 121.8(5) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 121.6(6) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 117.5(5) . . ?
C18 C19 H19 121.3 . . ?
C20 C19 H19 121.3 . . ?
C19 C20 C15 119.8(5) . . ?
C19 C20 C21 135.0(5) . . ?
C15 C20 C21 105.1(4) . . ?
C22 C21 C20 107.2(4) . . ?
C22 C21 C28 112.9(4) . . ?
C20 C21 C28 139.6(4) . . ?
C21 C22 N3 111.1(4) . . ?
C21 C22 C11 115.2(4) . . ?
N3 C22 C11 133.6(4) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C23 C24 C25 115.2(8) . . ?
C23 C24 H24A 108.5 . . ?
C25 C24 H24A 108.5 . . ?
C23 C24 H24B 108.5 . . ?
C25 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C24 C25 C26 114.4(6) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
N4 C26 C25 111.5(5) . . ?
N4 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
N4 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
O3 C27 N4 126.6(4) . . ?
O3 C27 C28 124.9(4) . . ?
N4 C27 C28 108.5(4) . . ?
C21 C28 C29 115.5(4) . . ?
C21 C28 C27 114.3(4) . . ?
C29 C28 C27 101.3(3) . . ?
C21 C28 C12 101.6(3) . . ?
C29 C28 C12 115.8(4) . . ?
C27 C28 C12 108.7(4) . . ?
C30 C29 C35 119.9(4) . . ?
C30 C29 C28 131.5(4) . . ?
C35 C29 C28 108.6(4) . . ?
C29 C30 C31 120.8(4) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C33 C31 C30 117.9(5) . . ?
C33 C31 C32 120.2(5) . . ?
C30 C31 C32 121.9(5) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C31 122.8(5) . . ?
C34 C33 H33 118.6 . . ?
C31 C33 H33 118.6 . . ?
C33 C34 C35 118.2(4) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 H34 120.9 . . ?
C34 C35 C29 120.3(5) . . ?
C34 C35 N4 130.0(4) . . ?
C29 C35 N4 109.7(4) . . ?
C9 N1 C2 108.8(4) . . ?
C9 N1 C1 126.4(5) . . ?
C2 N1 C1 124.7(5) . . ?
C10 N2 C13 111.8(4) . . ?
C10 N2 C14 122.8(4) . . ?
C13 N2 C14 125.3(4) . . ?
C22 N3 C15 107.6(4) . . ?
C22 N3 H3A 126.2 . . ?
C15 N3 H3A 126.2 . . ?
C27 N4 C35 111.9(4) . . ?
C27 N4 C26 123.3(5) . . ?
C35 N4 C26 124.0(4) . . ?
Cl3 C36 Cl1 111.6(4) . . ?
Cl3 C36 Cl2 112.3(5) . . ?
Cl1 C36 Cl2 108.6(4) . . ?
Cl3 C36 H36 108.0 . . ?
Cl1 C36 H36 108.0 . . ?
Cl2 C36 H36 108.0 . . ?

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
N3 H3A O1 0.86 2.17 2.973(5) 155.5 3_667

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_5e
_database_code_depnum_ccdc_archive 'CCDC 2177756'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H32 N4 O3'
_chemical_formula_sum            'C43 H32 N4 O3'
_chemical_formula_weight         652.72

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   29.965(6)
_cell_length_b                   10.1561(19)
_cell_length_c                   27.430(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.793(6)
_cell_angle_gamma                90
_cell_volume                     8171(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8913
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      21.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_F_000             2736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            34118
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7151
_reflns_number_gt                4092
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²+14.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7151
_refine_ls_number_parameters     499
_refine_ls_number_restraints     246
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.1073
_refine_ls_wR_factor_ref         0.3406
_refine_ls_wR_factor_gt          0.3132
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.52663(19) 0.4873(10) 0.4148(3) 0.144(3) Uani 1 1 d . . . . .
H1A H 0.5411 0.5065 0.3874 0.216 Uiso 1 1 calc R U . . .
H1B H 0.5331 0.3979 0.4253 0.216 Uiso 1 1 calc R U . . .
H1C H 0.5381 0.5458 0.4419 0.216 Uiso 1 1 calc R U . . .
C2 C 0.45083(17) 0.4559(6) 0.35692(19) 0.0833(14) Uani 1 1 d . . . . .
C3 C 0.4628(2) 0.3796(7) 0.3183(2) 0.113(2) Uani 1 1 d . . . . .
H3 H 0.4931 0.3588 0.3186 0.135 Uiso 1 1 calc R U . . .
C4 C 0.4288(3) 0.3379(8) 0.2809(3) 0.127(2) Uani 1 1 d . . . . .
H4 H 0.4360 0.2873 0.2554 0.152 Uiso 1 1 calc R U . . .
C5 C 0.3830(3) 0.3691(8) 0.2799(2) 0.120(2) Uani 1 1 d . . . . .
H5 H 0.3605 0.3397 0.2536 0.144 Uiso 1 1 calc R U . . .
C6 C 0.37113(19) 0.4422(6) 0.31706(19) 0.0923(16) Uani 1 1 d . . . . .
H6 H 0.3407 0.4630 0.3162 0.111 Uiso 1 1 calc R U . . .
C7 C 0.40540(15) 0.4856(5) 0.35655(16) 0.0708(12) Uani 1 1 d . . . . .
C8 C 0.40515(14) 0.5582(5) 0.40160(16) 0.0661(11) Uani 1 1 d . . . . .
C9 C 0.44987(16) 0.5651(6) 0.42527(18) 0.0836(14) Uani 1 1 d . . . . .
H9 H 0.4602 0.6062 0.4558 0.100 Uiso 1 1 calc R U . . .
C10 C 0.33370(14) 0.6991(4) 0.38560(15) 0.0613(11) Uani 1 1 d . . . . .
C11 C 0.36464(13) 0.6057(4) 0.42105(14) 0.0581(10) Uani 1 1 d . . . . .
C12 C 0.33079(13) 0.4950(4) 0.43057(14) 0.0581(10) Uani 1 1 d . . . . .
H12 H 0.3409 0.4097 0.4202 0.070 Uiso 1 1 calc R U . . .
C13 C 0.28573(15) 0.5307(4) 0.39808(14) 0.0592(10) Uani 1 1 d . . . . .
C14 C 0.25032(16) 0.7217(5) 0.34651(17) 0.0776(13) Uani 1 1 d . . . . .
H14A H 0.2563 0.8156 0.3487 0.093 Uiso 1 1 calc R U . . .
H14B H 0.2237 0.7047 0.3605 0.093 Uiso 1 1 calc R U . . .
C15 C 0.24029(18) 0.6808(6) 0.29212(16) 0.0978(14) Uani 1 1 d D U . . .
C16 C 0.1981(3) 0.6229(13) 0.2735(3) 0.1098(19) Uani 0.519(8) 1 d D U P A 1
H16 H 0.1784 0.6056 0.2949 0.132 Uiso 0.519(8) 1 calc R U P A 1
C17 C 0.1852(3) 0.5908(15) 0.2234(3) 0.1156(19) Uani 0.519(8) 1 d D U P A 1
H17 H 0.1550 0.5697 0.2099 0.139 Uiso 0.519(8) 1 calc R U P A 1
C18 C 0.2174(4) 0.5901(14) 0.1935(3) 0.1172(18) Uani 0.519(8) 1 d D U P A 1
H18 H 0.2108 0.5512 0.1622 0.141 Uiso 0.519(8) 1 calc R U P A 1
C19 C 0.2594(3) 0.6482(14) 0.2110(3) 0.1148(18) Uani 0.519(8) 1 d D U P A 1
H19 H 0.2812 0.6509 0.1913 0.138 Uiso 0.519(8) 1 calc R U P A 1
C20 C 0.2685(3) 0.7025(13) 0.2584(2) 0.1096(18) Uani 0.519(8) 1 d D U P A 1
H20 H 0.2942 0.7549 0.2680 0.132 Uiso 0.519(8) 1 calc R U P A 1
C16' C 0.2119(5) 0.5769(11) 0.2738(3) 0.1113(19) Uani 0.481(8) 1 d D U P A 2
H16' H 0.1986 0.5260 0.2952 0.134 Uiso 0.481(8) 1 calc R U P A 2
C17' C 0.2033(5) 0.5491(11) 0.2231(3) 0.1156(19) Uani 0.481(8) 1 d D U P A 2
H17' H 0.1881 0.4726 0.2108 0.139 Uiso 0.481(8) 1 calc R U P A 2
C18' C 0.2181(5) 0.6382(12) 0.1913(3) 0.1172(19) Uani 0.481(8) 1 d D U P A 2
H18' H 0.2093 0.6279 0.1570 0.141 Uiso 0.481(8) 1 calc R U P A 2
C19' C 0.2459(4) 0.7421(13) 0.2108(3) 0.1152(18) Uani 0.481(8) 1 d D U P A 2
H19' H 0.2613 0.7896 0.1904 0.138 Uiso 0.481(8) 1 calc R U P A 2
C20' C 0.2507(5) 0.7749(10) 0.2596(3) 0.1104(18) Uani 0.481(8) 1 d D U P A 2
H20' H 0.2608 0.8582 0.2709 0.133 Uiso 0.481(8) 1 calc R U P A 2
C21 C 0.39798(14) 0.7899(5) 0.53914(18) 0.0695(12) Uani 1 1 d . . . . .
C22 C 0.41812(18) 0.8821(6) 0.5739(2) 0.0942(17) Uani 1 1 d . . . . .
H22 H 0.4362 0.9494 0.5656 0.113 Uiso 1 1 calc R U . . .
C23 C 0.4100(2) 0.8696(8) 0.6217(3) 0.114(2) Uani 1 1 d . . . . .
H23 H 0.4230 0.9301 0.6460 0.136 Uiso 1 1 calc R U . . .
C24 C 0.3835(2) 0.7707(8) 0.6341(2) 0.109(2) Uani 1 1 d . . . . .
H24 H 0.3794 0.7645 0.6667 0.131 Uiso 1 1 calc R U . . .
C25 C 0.36250(18) 0.6793(6) 0.59939(18) 0.0870(15) Uani 1 1 d . . . . .
H25 H 0.3436 0.6147 0.6082 0.104 Uiso 1 1 calc R U . . .
C26 C 0.37012(14) 0.6857(5) 0.55167(15) 0.0650(12) Uani 1 1 d . . . . .
C27 C 0.35688(13) 0.6116(4) 0.50640(14) 0.0572(10) Uani 1 1 d . . . . .
C28 C 0.37598(13) 0.6694(4) 0.47143(15) 0.0592(10) Uani 1 1 d . . . . .
C29 C 0.35348(15) 0.3641(4) 0.51211(15) 0.0631(11) Uani 1 1 d . . . . .
C30 C 0.32952(13) 0.4904(4) 0.48809(14) 0.0567(10) Uani 1 1 d . . . . .
C31 C 0.28418(13) 0.4842(4) 0.50494(13) 0.0543(10) Uani 1 1 d . . . . .
C32 C 0.24748(15) 0.5691(5) 0.49683(16) 0.0680(11) Uani 1 1 d . . . . .
H32 H 0.2466 0.6408 0.4756 0.082 Uiso 1 1 calc R U . . .
C33 C 0.21195(16) 0.5457(6) 0.52093(19) 0.0798(14) Uani 1 1 d . . . . .
H33 H 0.1873 0.6031 0.5162 0.096 Uiso 1 1 calc R U . . .
C34 C 0.21266(17) 0.4390(6) 0.55159(19) 0.0842(15) Uani 1 1 d . . . . .
H34 H 0.1878 0.4232 0.5663 0.101 Uiso 1 1 calc R U . . .
C35 C 0.24943(17) 0.3547(5) 0.56110(17) 0.0773(13) Uani 1 1 d . . . . .
H35 H 0.2502 0.2841 0.5829 0.093 Uiso 1 1 calc R U . . .
C36 C 0.28527(14) 0.3779(4) 0.53722(14) 0.0599(10) Uani 1 1 d . . . . .
C37 C 0.33953(18) 0.1945(5) 0.57268(17) 0.0758(13) Uani 1 1 d . . . . .
H37A H 0.3616 0.1439 0.5591 0.091 Uiso 1 1 calc R U . . .
H37B H 0.3130 0.1391 0.5720 0.091 Uiso 1 1 calc R U . . .
C38 C 0.3599(3) 0.2295(7) 0.6259(3) 0.1293(18) Uani 1 1 d . U . . .
C39 C 0.3775(3) 0.3386(9) 0.6445(3) 0.156(2) Uani 1 1 d . U . . .
H39 H 0.3748 0.4087 0.6222 0.187 Uiso 1 1 calc R U . . .
C40 C 0.3999(4) 0.3669(10) 0.6924(3) 0.168(2) Uani 1 1 d . U . . .
H40 H 0.4186 0.4401 0.7002 0.202 Uiso 1 1 calc R U . . .
C41 C 0.3928(4) 0.2850(11) 0.7250(4) 0.172(2) Uani 1 1 d . U . . .
H41 H 0.4039 0.3043 0.7584 0.206 Uiso 1 1 calc R U . . .
C42 C 0.3696(4) 0.1703(10) 0.7131(3) 0.165(2) Uani 1 1 d . U . . .
H42 H 0.3651 0.1120 0.7378 0.198 Uiso 1 1 calc R U . . .
C43 C 0.3530(3) 0.1429(9) 0.6636(3) 0.148(2) Uani 1 1 d . U . . .
H43 H 0.3368 0.0653 0.6549 0.177 Uiso 1 1 calc R U . . .
N1 N 0.47679(13) 0.5051(5) 0.39873(17) 0.0921(13) Uani 1 1 d . . . . .
N2 N 0.29009(11) 0.6506(4) 0.37646(12) 0.0624(9) Uani 1 1 d . . . . .
N3 N 0.40071(11) 0.7767(4) 0.49018(14) 0.0685(10) Uani 1 1 d . . . . .
H3A H 0.4155 0.8276 0.4741 0.082 Uiso 1 1 calc R U . . .
N4 N 0.32595(12) 0.3095(3) 0.54095(12) 0.0623(9) Uani 1 1 d . . . . .
O1 O 0.34540(12) 0.8009(4) 0.36866(13) 0.0915(11) Uani 1 1 d . . . . .
O2 O 0.25090(11) 0.4679(4) 0.39122(11) 0.0824(10) Uani 1 1 d . . . . .
O3 O 0.38923(11) 0.3234(3) 0.50603(13) 0.0870(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.479(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.343(7) . ?
C2 C7 1.392(6) . ?
C2 C3 1.416(8) . ?
C3 C4 1.358(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.440(6) . ?
C8 C9 1.366(6) . ?
C8 C11 1.502(6) . ?
C9 N1 1.339(6) . ?
C9 H9 0.9300 . ?
C10 O1 1.213(5) . ?
C10 N2 1.371(5) . ?
C10 C11 1.529(6) . ?
C11 C28 1.501(6) . ?
C11 C12 1.571(6) . ?
C12 C13 1.502(6) . ?
C12 C30 1.587(5) . ?
C12 H12 0.9800 . ?
C13 O2 1.204(5) . ?
C13 N2 1.373(5) . ?
C14 N2 1.489(5) . ?
C14 C15 1.518(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16' 1.385(5) . ?
C15 C20' 1.387(5) . ?
C15 C20 1.391(4) . ?
C15 C16 1.392(5) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C16' C17' 1.388(5) . ?
C16' H16' 0.9300 . ?
C17' C18' 1.391(5) . ?
C17' H17' 0.9300 . ?
C18' C19' 1.381(5) . ?
C18' H18' 0.9300 . ?
C19' C20' 1.358(11) . ?
C19' H19' 0.9300 . ?
C20' H20' 0.9300 . ?
C21 N3 1.369(6) . ?
C21 C22 1.383(7) . ?
C21 C26 1.432(7) . ?
C22 C23 1.389(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.437(6) . ?
C27 C28 1.348(6) . ?
C27 C30 1.507(6) . ?
C28 N3 1.359(5) . ?
C29 O3 1.191(5) . ?
C29 N4 1.372(6) . ?
C29 C30 1.549(6) . ?
C30 C31 1.523(6) . ?
C31 C32 1.379(6) . ?
C31 C36 1.392(6) . ?
C32 C33 1.384(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.369(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.378(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(6) . ?
C35 H35 0.9300 . ?
C36 N4 1.389(5) . ?
C37 N4 1.464(5) . ?
C37 C38 1.506(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.287(10) . ?
C38 C43 1.404(10) . ?
C39 C40 1.379(11) . ?
C39 H39 0.9300 . ?
C40 C41 1.270(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.362(13) . ?
C41 H41 0.9300 . ?
C42 C43 1.376(11) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
N3 H3A 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 108.7(4) . . ?
N1 C2 C3 130.6(5) . . ?
C7 C2 C3 120.7(5) . . ?
C4 C3 C2 118.0(6) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.7(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.7(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.1(6) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 119.9(5) . . ?
C2 C7 C8 106.3(4) . . ?
C6 C7 C8 133.8(4) . . ?
C9 C8 C7 104.9(4) . . ?
C9 C8 C11 126.9(4) . . ?
C7 C8 C11 128.0(4) . . ?
N1 C9 C8 111.1(4) . . ?
N1 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?
O1 C10 N2 125.1(4) . . ?
O1 C10 C11 125.9(4) . . ?
N2 C10 C11 108.9(4) . . ?
C28 C11 C8 114.7(3) . . ?
C28 C11 C10 108.2(3) . . ?
C8 C11 C10 113.7(3) . . ?
C28 C11 C12 100.8(3) . . ?
C8 C11 C12 115.2(4) . . ?
C10 C11 C12 102.8(3) . . ?
C13 C12 C11 105.1(3) . . ?
C13 C12 C30 113.3(3) . . ?
C11 C12 C30 109.5(3) . . ?
C13 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
C30 C12 H12 109.6 . . ?
O2 C13 N2 123.9(4) . . ?
O2 C13 C12 127.6(4) . . ?
N2 C13 C12 108.5(3) . . ?
N2 C14 C15 112.7(4) . . ?
N2 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N2 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16' C15 C20' 119.6(6) . . ?
C20 C15 C16 116.9(5) . . ?
C16' C15 C14 123.3(5) . . ?
C20' C15 C14 114.8(6) . . ?
C20 C15 C14 125.7(5) . . ?
C16 C15 C14 117.3(5) . . ?
C17 C16 C15 120.7(6) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.9(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.0(6) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 119.1(6) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C15 122.0(6) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
C15 C16' C17' 119.5(6) . . ?
C15 C16' H16' 120.2 . . ?
C17' C16' H16' 120.2 . . ?
C16' C17' C18' 118.5(6) . . ?
C16' C17' H17' 120.7 . . ?
C18' C17' H17' 120.7 . . ?
C19' C18' C17' 119.9(6) . . ?
C19' C18' H18' 120.0 . . ?
C17' C18' H18' 120.0 . . ?
C20' C19' C18' 120.2(7) . . ?
C20' C19' H19' 119.9 . . ?
C18' C19' H19' 119.9 . . ?
C19' C20' C15 118.2(6) . . ?
C19' C20' H20' 120.9 . . ?
C15 C20' H20' 120.9 . . ?
N3 C21 C22 129.6(5) . . ?
N3 C21 C26 108.5(4) . . ?
C22 C21 C26 121.9(5) . . ?
C21 C22 C23 117.0(6) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
C24 C23 C22 121.6(6) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 121.9(6) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C26 C25 C24 118.8(6) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C21 118.8(4) . . ?
C25 C26 C27 136.7(5) . . ?
C21 C26 C27 104.5(4) . . ?
C28 C27 C26 107.7(4) . . ?
C28 C27 C30 113.6(3) . . ?
C26 C27 C30 138.7(4) . . ?
C27 C28 N3 111.0(4) . . ?
C27 C28 C11 114.7(4) . . ?
N3 C28 C11 134.3(4) . . ?
O3 C29 N4 127.2(4) . . ?
O3 C29 C30 125.4(4) . . ?
N4 C29 C30 107.4(4) . . ?
C27 C30 C31 113.0(3) . . ?
C27 C30 C29 111.2(3) . . ?
C31 C30 C29 101.6(3) . . ?
C27 C30 C12 100.7(3) . . ?
C31 C30 C12 120.5(3) . . ?
C29 C30 C12 110.1(3) . . ?
C32 C31 C36 120.1(4) . . ?
C32 C31 C30 131.0(4) . . ?
C36 C31 C30 108.6(3) . . ?
C31 C32 C33 118.8(4) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
C34 C33 C32 120.9(5) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 121.3(5) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C34 C35 C36 118.1(5) . . ?
C34 C35 H35 121.0 . . ?
C36 C35 H35 121.0 . . ?
C35 C36 N4 129.2(4) . . ?
C35 C36 C31 120.8(4) . . ?
N4 C36 C31 109.9(4) . . ?
N4 C37 C38 113.4(4) . . ?
N4 C37 H37A 108.9 . . ?
C38 C37 H37A 108.9 . . ?
N4 C37 H37B 108.9 . . ?
C38 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C39 C38 C43 111.1(7) . . ?
C39 C38 C37 129.6(7) . . ?
C43 C38 C37 118.3(7) . . ?
C38 C39 C40 129.5(9) . . ?
C38 C39 H39 115.2 . . ?
C40 C39 H39 115.2 . . ?
C41 C40 C39 114.6(10) . . ?
C41 C40 H40 122.7 . . ?
C39 C40 H40 122.7 . . ?
C40 C41 C42 122.8(9) . . ?
C40 C41 H41 118.6 . . ?
C42 C41 H41 118.6 . . ?
C41 C42 C43 118.3(9) . . ?
C41 C42 H42 120.9 . . ?
C43 C42 H42 120.9 . . ?
C42 C43 C38 121.4(8) . . ?
C42 C43 H43 119.3 . . ?
C38 C43 H43 119.3 . . ?
C9 N1 C2 109.0(4) . . ?
C9 N1 C1 125.3(5) . . ?
C2 N1 C1 125.6(5) . . ?
C10 N2 C13 114.3(3) . . ?
C10 N2 C14 123.5(4) . . ?
C13 N2 C14 122.2(4) . . ?
C28 N3 C21 108.2(4) . . ?
C28 N3 H3A 125.9 . . ?
C21 N3 H3A 125.9 . . ?
C29 N4 C36 112.2(3) . . ?
C29 N4 C37 122.6(4) . . ?
C36 N4 C37 125.2(4) . . ?

_refine_diff_density_max         0.942
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.071


####################################################################### 
# 
# 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_5j
_database_code_depnum_ccdc_archive 'CCDC 2177757'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 F N4 O3'
_chemical_formula_sum            'C37 H27 F N4 O3'
_chemical_formula_weight         594.62

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   30.155(3)
_cell_length_b                   9.1523(9)
_cell_length_c                   25.150(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6941.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6274
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      19.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             2480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            67793
_diffrn_reflns_av_unetI/netI     0.1644
_diffrn_reflns_av_R_equivalents  0.1808
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             12103
_reflns_number_gt                5457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1766P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0018(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12103
_refine_ls_number_parameters     816
_refine_ls_number_restraints     213
_refine_ls_R_factor_all          0.2335
_refine_ls_R_factor_gt           0.1035
_refine_ls_wR_factor_ref         0.3010
_refine_ls_wR_factor_gt          0.2609
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5208(5) -0.092(3) 0.3142(7) 0.157(6) Uani 1 1 d . U . . .
H1A H 0.5161 -0.1899 0.3021 0.235 Uiso 1 1 calc R U . . .
H1B H 0.5123 -0.0243 0.2868 0.235 Uiso 1 1 calc R U . . .
H1C H 0.5031 -0.0743 0.3454 0.235 Uiso 1 1 calc R U . . .
C2 C 0.6034(3) -0.096(2) 0.2929(4) 0.111(3) Uani 1 1 d D U . . .
C3 C 0.6034(4) -0.121(2) 0.2382(4) 0.115(3) Uani 1 1 d D U . . .
H3 H 0.5770 -0.1412 0.2205 0.138 Uiso 1 1 calc R U . . .
C4 C 0.6429(4) -0.117(2) 0.2109(4) 0.113(3) Uani 1 1 d D U . . .
H4 H 0.6439 -0.1447 0.1753 0.136 Uiso 1 1 calc R U . . .
C5 C 0.6814(4) -0.072(2) 0.2364(4) 0.110(3) Uani 1 1 d D U . . .
H5 H 0.7079 -0.0679 0.2177 0.132 Uiso 1 1 calc R U . . .
C6 C 0.6805(3) -0.031(2) 0.2895(4) 0.102(3) Uani 1 1 d D U . . .
H6 H 0.7059 0.0042 0.3059 0.122 Uiso 1 1 calc R U . . .
C7 C 0.6412(3) -0.045(2) 0.3179(4) 0.097(3) Uani 1 1 d D U . . .
C8 C 0.6277(4) -0.003(2) 0.3718(5) 0.093(3) Uani 1 1 d . U . . .
C9 C 0.5849(4) -0.028(2) 0.3751(5) 0.106(3) Uani 1 1 d . U . . .
H9 H 0.5684 -0.0185 0.4061 0.127 Uiso 1 1 calc R U . . .
C10 C 0.6300(4) 0.0909(14) 0.4628(5) 0.064(3) Uani 1 1 d . . . . .
C11 C 0.6573(4) 0.0623(12) 0.4141(4) 0.049(3) Uani 1 1 d . . . . .
C12 C 0.6949(3) -0.0424(11) 0.4357(4) 0.045(3) Uani 1 1 d . . . . .
H12 H 0.6986 -0.1265 0.4120 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6792(4) -0.0901(13) 0.4881(5) 0.059(3) Uani 1 1 d . . . . .
C14 C 0.6220(4) -0.0015(14) 0.5572(5) 0.074(4) Uani 1 1 d . . . . .
H14A H 0.6228 -0.0978 0.5722 0.110 Uiso 1 1 calc R U . . .
H14B H 0.5918 0.0303 0.5541 0.110 Uiso 1 1 calc R U . . .
H14C H 0.6380 0.0647 0.5798 0.110 Uiso 1 1 calc R U . . .
C15 C 0.7129(6) 0.3969(14) 0.3662(5) 0.066(4) Uani 1 1 d . . . . .
C16 C 0.7185(8) 0.5315(16) 0.3445(6) 0.098(6) Uani 1 1 d . . . . .
H16 H 0.6951 0.5841 0.3298 0.117 Uiso 1 1 calc R U . . .
C17 C 0.7602(12) 0.5835(18) 0.3457(6) 0.128(10) Uani 1 1 d . . . . .
H17 H 0.7649 0.6754 0.3310 0.154 Uiso 1 1 calc R U . . .
C18 C 0.7972(7) 0.512(2) 0.3669(7) 0.106(6) Uani 1 1 d . . . . .
H18 H 0.8248 0.5577 0.3669 0.127 Uiso 1 1 calc R U . . .
C19 C 0.7923(5) 0.3756(15) 0.3876(5) 0.076(4) Uani 1 1 d . . . . .
H19 H 0.8161 0.3206 0.4000 0.091 Uiso 1 1 calc R U . . .
C20 C 0.7451(6) 0.3208(12) 0.3888(5) 0.077(4) Uani 1 1 d . . . . .
C21 C 0.7274(4) 0.1836(12) 0.4098(5) 0.057(3) Uani 1 1 d . . . . .
C22 C 0.6827(4) 0.1922(14) 0.3966(4) 0.059(3) Uani 1 1 d . . . . .
C23 C 0.8908(3) 0.0616(13) 0.4046(4) 0.077(4) Uani 1 1 d D . . . .
H23 H 0.8676 0.0694 0.3802 0.092 Uiso 1 1 calc R U . . .
C24 C 0.9257(4) 0.1603(12) 0.4017(5) 0.070(4) Uani 1 1 d D . . . .
H24 H 0.9253 0.2353 0.3768 0.084 Uiso 1 1 calc R U . . .
C25 C 0.9610(4) 0.1455(16) 0.4365(6) 0.102(6) Uani 1 1 d D . . . .
H25 H 0.9850 0.2093 0.4349 0.122 Uiso 1 1 calc R U . . .
C26 C 0.9600(4) 0.0341(17) 0.4737(6) 0.099(5) Uani 1 1 d D . . . .
H26 H 0.9833 0.0252 0.4977 0.119 Uiso 1 1 calc R U . . .
C27 C 0.9254(4) -0.0643(15) 0.4761(5) 0.088(5) Uani 1 1 d D . . . .
H27 H 0.9262 -0.1412 0.5002 0.106 Uiso 1 1 calc R U . . .
C28 C 0.8892(3) -0.0479(12) 0.4423(5) 0.067(4) Uani 1 1 d D . . . .
C29 C 0.8478(4) -0.1489(14) 0.4445(6) 0.072(4) Uani 1 1 d . . . . .
H29A H 0.8459 -0.2042 0.4117 0.086 Uiso 1 1 calc R U . . .
H29B H 0.8513 -0.2179 0.4735 0.086 Uiso 1 1 calc R U . . .
C30 C 0.7779(4) -0.0394(12) 0.4140(6) 0.057(3) Uani 1 1 d . . . . .
C31 C 0.7394(3) 0.0451(11) 0.4404(4) 0.046(3) Uani 1 1 d . . . . .
C32 C 0.7567(4) 0.0725(13) 0.4962(5) 0.054(2) Uani 1 1 d . U . . .
C33 C 0.7395(4) 0.1558(13) 0.5367(5) 0.063(2) Uani 1 1 d . U . . .
H33 H 0.7127 0.2051 0.5335 0.076 Uiso 1 1 calc R U . . .
C34 C 0.7657(4) 0.1615(15) 0.5846(5) 0.075(3) Uani 1 1 d . U . . .
C35 C 0.8036(5) 0.0848(14) 0.5887(6) 0.077(4) Uani 1 1 d . U . . .
H35 H 0.8188 0.0874 0.6209 0.092 Uiso 1 1 calc R U . . .
C36 C 0.8213(4) 0.0019(13) 0.5475(5) 0.062(3) Uani 1 1 d . U . . .
H36 H 0.8481 -0.0480 0.5506 0.074 Uiso 1 1 calc R U . . .
C37 C 0.7966(4) -0.0003(13) 0.5025(5) 0.055(2) Uani 1 1 d . U . . .
C38 C 0.7865(5) 0.804(2) 0.1817(7) 0.129(7) Uani 1 1 d . . . . .
H38A H 0.7861 0.8920 0.1608 0.194 Uiso 1 1 calc R U . . .
H38B H 0.7827 0.8287 0.2186 0.194 Uiso 1 1 calc R U . . .
H38C H 0.7629 0.7411 0.1706 0.194 Uiso 1 1 calc R U . . .
C39 C 0.8656(3) 0.7216(13) 0.2121(4) 0.065(3) Uani 1 1 d D . . . .
C40 C 0.8698(4) 0.7894(13) 0.2609(4) 0.075(4) Uani 1 1 d D . . . .
H40 H 0.8470 0.8461 0.2747 0.090 Uiso 1 1 calc R U . . .
C41 C 0.9091(4) 0.7709(14) 0.2888(4) 0.081(4) Uani 1 1 d D . . . .
H41 H 0.9124 0.8131 0.3222 0.097 Uiso 1 1 calc R U . . .
C42 C 0.9434(4) 0.6902(15) 0.2672(4) 0.084(4) Uani 1 1 d D . . . .
H42 H 0.9696 0.6790 0.2862 0.101 Uiso 1 1 calc R U . . .
C43 C 0.9392(3) 0.6257(13) 0.2175(4) 0.068(4) Uani 1 1 d D . . . .
H43 H 0.9622 0.5696 0.2036 0.082 Uiso 1 1 calc R U . . .
C44 C 0.9002(3) 0.6460(11) 0.1889(3) 0.054(3) Uani 1 1 d D . . . .
C45 C 0.8846(3) 0.6001(12) 0.1370(4) 0.048(3) Uani 1 1 d . . . . .
C46 C 0.8424(4) 0.6508(13) 0.1321(5) 0.067(3) Uani 1 1 d . . . . .
H46 H 0.8243 0.6339 0.1028 0.080 Uiso 1 1 calc R U . . .
C47 C 0.8809(4) 0.4827(12) 0.0478(4) 0.045(3) Uani 1 1 d . . . . .
C48 C 0.9105(3) 0.5150(11) 0.0964(4) 0.040(3) Uani 1 1 d . . . . .
C49 C 0.9503(3) 0.6028(11) 0.0688(4) 0.046(3) Uani 1 1 d . . . . .
H49 H 0.9573 0.6906 0.0895 0.055 Uiso 1 1 calc R U . . .
C50 C 0.9321(4) 0.6437(13) 0.0174(5) 0.055(3) Uani 1 1 d . . . . .
C51 C 0.8731(5) 0.5578(17) -0.0439(5) 0.086(4) Uani 1 1 d . . . . .
H51A H 0.8835 0.4747 -0.0636 0.130 Uiso 1 1 calc R U . . .
H51B H 0.8798 0.6456 -0.0633 0.130 Uiso 1 1 calc R U . . .
H51C H 0.8416 0.5503 -0.0389 0.130 Uiso 1 1 calc R U . . .
C52 C 0.9569(4) 0.1621(11) 0.1438(4) 0.055(3) Uani 1 1 d . . . . .
C53 C 0.9578(4) 0.0239(13) 0.1657(5) 0.068(4) Uani 1 1 d . . . . .
H53 H 0.9336 -0.0154 0.1836 0.081 Uiso 1 1 calc R U . . .
C54 C 0.9987(6) -0.0555(16) 0.1593(6) 0.087(5) Uani 1 1 d . . . . .
H54 H 1.0017 -0.1492 0.1731 0.105 Uiso 1 1 calc R U . . .
C55 C 1.0338(5) 0.0099(16) 0.1321(6) 0.073(4) Uani 1 1 d . . . . .
H55 H 1.0596 -0.0440 0.1272 0.088 Uiso 1 1 calc R U . . .
C56 C 1.0323(4) 0.1542(12) 0.1113(4) 0.056(3) Uani 1 1 d . . . . .
H56 H 1.0569 0.1967 0.0953 0.067 Uiso 1 1 calc R U . . .
C57 C 0.9932(4) 0.2276(11) 0.1161(4) 0.048(3) Uani 1 1 d . . . . .
C58 C 0.9759(4) 0.3643(12) 0.0991(4) 0.050(3) Uani 1 1 d . . . . .
C59 C 0.9336(4) 0.3793(11) 0.1139(4) 0.046(3) Uani 1 1 d . . . . .
C60 C 1.1460(4) 0.4482(14) 0.0949(6) 0.073(4) Uani 1 1 d . . . . .
H60 H 1.1216 0.4341 0.1169 0.088 Uiso 1 1 calc R U . . .
C61 C 1.1836(6) 0.354(2) 0.0992(7) 0.107(5) Uani 1 1 d . . . . .
H61 H 1.1859 0.2841 0.1258 0.128 Uiso 1 1 calc R U . . .
C62 C 1.2146(6) 0.3729(14) 0.0633(8) 0.089(5) Uani 1 1 d . . . . .
H62 H 1.2396 0.3135 0.0655 0.107 Uiso 1 1 calc R U . . .
C63 C 1.2133(4) 0.4690(17) 0.0242(6) 0.076(4) Uani 1 1 d . . . . .
H63 H 1.2347 0.4700 -0.0025 0.091 Uiso 1 1 calc R U . . .
C64 C 1.1793(4) 0.5669(16) 0.0247(6) 0.077(4) Uani 1 1 d . . . . .
H64 H 1.1792 0.6431 0.0003 0.092 Uiso 1 1 calc R U . . .
C65 C 1.1459(4) 0.5559(13) 0.0594(5) 0.066(4) Uani 1 1 d . . . . .
C66 C 1.1060(3) 0.6621(12) 0.0569(5) 0.057(3) Uani 1 1 d . . . . .
H66A H 1.1048 0.7186 0.0895 0.068 Uiso 1 1 calc R U . . .
H66B H 1.1102 0.7297 0.0276 0.068 Uiso 1 1 calc R U . . .
C67 C 1.0331(3) 0.5792(11) 0.0897(5) 0.044(3) Uani 1 1 d . . . . .
C68 C 0.9917(3) 0.4969(11) 0.0677(4) 0.037(2) Uani 1 1 d . . . . .
C69 C 1.0088(4) 0.4574(12) 0.0110(5) 0.0550(14) Uani 1 1 d . U . . .
C70 C 0.9893(4) 0.3740(12) -0.0284(4) 0.0557(14) Uani 1 1 d . U . . .
H70 H 0.9613 0.3338 -0.0234 0.067 Uiso 1 1 calc R U . . .
C71 C 1.0117(4) 0.3513(13) -0.0748(5) 0.0563(14) Uani 1 1 d . U . . .
C72 C 1.0552(4) 0.4129(12) -0.0831(5) 0.0567(14) Uani 1 1 d . U . . .
H72 H 1.0698 0.3974 -0.1151 0.068 Uiso 1 1 calc R U . . .
C73 C 1.0754(4) 0.4955(13) -0.0434(4) 0.0563(14) Uani 1 1 d . U . . .
H73 H 1.1034 0.5362 -0.0480 0.068 Uiso 1 1 calc R U . . .
C74 C 1.0504(4) 0.5144(12) 0.0053(5) 0.0553(14) Uani 1 1 d . U . . .
F1 F 0.7485(3) 0.2394(11) 0.6251(3) 0.120(3) Uani 1 1 d . . . . .
F2 F 0.9940(3) 0.2776(10) -0.1151(3) 0.100(3) Uani 1 1 d . . . . .
N1 N 0.5677(4) -0.0711(18) 0.3271(4) 0.118(3) Uani 1 1 d . U . . .
N2 N 0.6430(3) -0.0037(10) 0.5034(3) 0.052(2) Uani 1 1 d . . . . .
N3 N 0.6749(4) 0.3149(10) 0.3711(4) 0.064(3) Uani 1 1 d . . . . .
H3A H 0.6494 0.3406 0.3590 0.077 Uiso 1 1 calc R U . . .
N4 N 0.8086(3) -0.0710(10) 0.4517(4) 0.052(2) Uani 1 1 d . . . . .
N5 N 0.8305(3) 0.7272(13) 0.1743(4) 0.077(3) Uani 1 1 d . . . . .
N6 N 0.8946(3) 0.5620(10) 0.0069(4) 0.053(2) Uani 1 1 d . . . . .
N7 N 0.9205(3) 0.2568(11) 0.1424(4) 0.065(3) Uani 1 1 d . . . . .
H7 H 0.8949 0.2419 0.1566 0.078 Uiso 1 1 calc R U . . .
N8 N 1.0640(3) 0.5849(9) 0.0498(4) 0.052(2) Uani 1 1 d . . . . .
O1 O 0.6018(3) 0.1837(11) 0.4675(3) 0.080(3) Uani 1 1 d . . . . .
O2 O 0.6943(3) -0.1863(9) 0.5177(3) 0.070(2) Uani 1 1 d . . . . .
O3 O 0.7809(3) -0.0728(9) 0.3672(4) 0.071(2) Uani 1 1 d . . . . .
O4 O 0.8492(3) 0.3992(9) 0.0468(3) 0.067(2) Uani 1 1 d . . . . .
O5 O 0.9490(3) 0.7412(10) -0.0128(4) 0.077(3) Uani 1 1 d . . . . .
O6 O 1.0368(2) 0.6211(9) 0.1344(3) 0.063(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.464(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.381(6) . ?
C2 C3 1.395(6) . ?
C2 N1 1.397(15) . ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.465(15) . ?
C8 C9 1.311(16) . ?
C8 C11 1.514(16) . ?
C9 N1 1.371(17) . ?
C9 H9 0.9300 . ?
C10 O1 1.208(14) . ?
C10 N2 1.396(14) . ?
C10 C11 1.499(17) . ?
C11 C22 1.482(16) . ?
C11 C12 1.581(15) . ?
C12 C13 1.467(16) . ?
C12 C31 1.567(14) . ?
C12 H12 0.9800 . ?
C13 O2 1.240(14) . ?
C13 N2 1.402(14) . ?
C14 N2 1.493(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.324(18) . ?
C15 C16 1.359(19) . ?
C15 N3 1.374(16) . ?
C16 C17 1.35(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.40(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.36(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.51(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.464(16) . ?
C21 C22 1.389(15) . ?
C21 C31 1.527(16) . ?
C22 N3 1.314(14) . ?
C23 C28 1.381(6) . ?
C23 C24 1.390(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.555(15) . ?
C29 N4 1.392(15) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 O3 1.218(14) . ?
C30 N4 1.357(15) . ?
C30 C31 1.547(15) . ?
C31 C32 1.518(15) . ?
C32 C33 1.374(15) . ?
C32 C37 1.385(16) . ?
C33 C34 1.441(16) . ?
C33 H33 0.9300 . ?
C34 C35 1.346(17) . ?
C34 F1 1.346(15) . ?
C35 C36 1.392(18) . ?
C35 H35 0.9300 . ?
C36 C37 1.354(15) . ?
C36 H36 0.9300 . ?
C37 N4 1.478(15) . ?
C38 N5 1.514(16) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.381(6) . ?
C39 C44 1.383(6) . ?
C39 N5 1.423(13) . ?
C40 C41 1.388(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.381(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.388(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.391(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.451(13) . ?
C45 C46 1.360(15) . ?
C45 C48 1.501(14) . ?
C46 N5 1.321(14) . ?
C46 H46 0.9300 . ?
C47 O4 1.226(12) . ?
C47 N6 1.326(13) . ?
C47 C48 1.542(15) . ?
C48 C59 1.491(15) . ?
C48 C49 1.604(15) . ?
C49 C50 1.456(15) . ?
C49 C68 1.579(14) . ?
C49 H49 0.9800 . ?
C50 O5 1.276(13) . ?
C50 N6 1.380(14) . ?
C51 N6 1.434(15) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.381(15) . ?
C52 N7 1.399(14) . ?
C52 C57 1.429(16) . ?
C53 C54 1.440(19) . ?
C53 H53 0.9300 . ?
C54 C55 1.40(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.420(18) . ?
C55 H55 0.9300 . ?
C56 C57 1.362(15) . ?
C56 H56 0.9300 . ?
C57 C58 1.421(14) . ?
C58 C59 1.337(14) . ?
C58 C68 1.523(14) . ?
C59 N7 1.389(13) . ?
C60 C65 1.330(16) . ?
C60 C61 1.43(2) . ?
C60 H60 0.9300 . ?
C61 C62 1.31(2) . ?
C61 H61 0.9300 . ?
C62 C63 1.32(2) . ?
C62 H62 0.9300 . ?
C63 C64 1.362(17) . ?
C63 H63 0.9300 . ?
C64 C65 1.336(16) . ?
C64 H64 0.9300 . ?
C65 C66 1.549(16) . ?
C66 N8 1.460(13) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?
C67 O6 1.191(13) . ?
C67 N8 1.373(13) . ?
C67 C68 1.560(14) . ?
C68 C69 1.560(15) . ?
C69 C74 1.366(16) . ?
C69 C70 1.383(15) . ?
C70 C71 1.362(14) . ?
C70 H70 0.9300 . ?
C71 F2 1.329(13) . ?
C71 C72 1.443(15) . ?
C72 C73 1.391(15) . ?
C72 H72 0.9300 . ?
C73 C74 1.449(15) . ?
C73 H73 0.9300 . ?
C74 N8 1.355(14) . ?
N3 H3A 0.8600 . ?
N7 H7 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 120.5(8) . . ?
C7 C2 N1 107.5(9) . . ?
C3 C2 N1 129.3(10) . . ?
C4 C3 C2 119.1(8) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.0(8) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.2(7) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 119.9(7) . . ?
C2 C7 C8 106.2(8) . . ?
C6 C7 C8 133.7(9) . . ?
C9 C8 C7 106.8(11) . . ?
C9 C8 C11 127.1(12) . . ?
C7 C8 C11 126.1(10) . . ?
C8 C9 N1 111.4(12) . . ?
C8 C9 H9 124.3 . . ?
N1 C9 H9 124.3 . . ?
O1 C10 N2 124.2(12) . . ?
O1 C10 C11 126.1(11) . . ?
N2 C10 C11 109.6(10) . . ?
C22 C11 C10 112.7(9) . . ?
C22 C11 C8 114.6(10) . . ?
C10 C11 C8 108.7(9) . . ?
C22 C11 C12 102.5(9) . . ?
C10 C11 C12 102.7(9) . . ?
C8 C11 C12 115.1(10) . . ?
C13 C12 C31 111.1(9) . . ?
C13 C12 C11 104.9(9) . . ?
C31 C12 C11 109.3(8) . . ?
C13 C12 H12 110.5 . . ?
C31 C12 H12 110.5 . . ?
C11 C12 H12 110.5 . . ?
O2 C13 N2 121.5(11) . . ?
O2 C13 C12 129.1(11) . . ?
N2 C13 C12 109.3(11) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 124.0(17) . . ?
C20 C15 N3 106.7(12) . . ?
C16 C15 N3 129.4(16) . . ?
C17 C16 C15 115.3(19) . . ?
C17 C16 H16 122.3 . . ?
C15 C16 H16 122.3 . . ?
C16 C17 C18 126.2(16) . . ?
C16 C17 H17 116.9 . . ?
C18 C17 H17 116.9 . . ?
C19 C18 C17 119.2(16) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 114.5(15) . . ?
C18 C19 H19 122.7 . . ?
C20 C19 H19 122.7 . . ?
C15 C20 C21 109.7(14) . . ?
C15 C20 C19 120.6(13) . . ?
C21 C20 C19 129.6(14) . . ?
C22 C21 C20 102.7(11) . . ?
C22 C21 C31 113.4(10) . . ?
C20 C21 C31 143.8(12) . . ?
N3 C22 C21 109.7(11) . . ?
N3 C22 C11 137.6(12) . . ?
C21 C22 C11 112.7(10) . . ?
C28 C23 C24 122.2(8) . . ?
C28 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C25 C24 C23 119.1(7) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 118.8(8) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C27 C26 C25 121.8(8) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 119.8(8) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 118.2(7) . . ?
C23 C28 C29 118.9(10) . . ?
C27 C28 C29 122.9(10) . . ?
N4 C29 C28 112.4(10) . . ?
N4 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
N4 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
O3 C30 N4 124.8(11) . . ?
O3 C30 C31 126.6(11) . . ?
N4 C30 C31 108.6(11) . . ?
C32 C31 C21 114.2(9) . . ?
C32 C31 C30 102.8(9) . . ?
C21 C31 C30 112.1(9) . . ?
C32 C31 C12 116.7(9) . . ?
C21 C31 C12 100.5(8) . . ?
C30 C31 C12 110.8(8) . . ?
C33 C32 C37 120.7(11) . . ?
C33 C32 C31 130.3(10) . . ?
C37 C32 C31 109.0(10) . . ?
C32 C33 C34 115.6(11) . . ?
C32 C33 H33 122.2 . . ?
C34 C33 H33 122.2 . . ?
C35 C34 F1 123.0(12) . . ?
C35 C34 C33 120.8(13) . . ?
F1 C34 C33 116.1(12) . . ?
C34 C35 C36 123.6(13) . . ?
C34 C35 H35 118.2 . . ?
C36 C35 H35 118.2 . . ?
C37 C36 C35 114.8(12) . . ?
C37 C36 H36 122.6 . . ?
C35 C36 H36 122.6 . . ?
C36 C37 C32 124.5(12) . . ?
C36 C37 N4 126.4(11) . . ?
C32 C37 N4 109.0(10) . . ?
N5 C38 H38A 109.5 . . ?
N5 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N5 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C44 121.9(7) . . ?
C40 C39 N5 130.3(8) . . ?
C44 C39 N5 107.3(8) . . ?
C39 C40 C41 118.3(7) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C42 C41 C40 120.3(7) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C41 C42 C43 121.0(7) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 119.0(7) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 H43 120.5 . . ?
C39 C44 C43 119.2(7) . . ?
C39 C44 C45 106.2(7) . . ?
C43 C44 C45 134.5(8) . . ?
C46 C45 C44 106.6(9) . . ?
C46 C45 C48 126.9(10) . . ?
C44 C45 C48 126.4(9) . . ?
N5 C46 C45 111.2(11) . . ?
N5 C46 H46 124.4 . . ?
C45 C46 H46 124.4 . . ?
O4 C47 N6 124.7(11) . . ?
O4 C47 C48 126.0(10) . . ?
N6 C47 C48 109.3(10) . . ?
C59 C48 C45 118.3(9) . . ?
C59 C48 C47 110.2(8) . . ?
C45 C48 C47 109.8(8) . . ?
C59 C48 C49 101.2(8) . . ?
C45 C48 C49 115.0(8) . . ?
C47 C48 C49 100.7(8) . . ?
C50 C49 C68 116.2(8) . . ?
C50 C49 C48 103.3(9) . . ?
C68 C49 C48 106.9(8) . . ?
C50 C49 H49 110.0 . . ?
C68 C49 H49 110.0 . . ?
C48 C49 H49 110.0 . . ?
O5 C50 N6 126.3(11) . . ?
O5 C50 C49 123.8(12) . . ?
N6 C50 C49 109.9(10) . . ?
N6 C51 H51A 109.5 . . ?
N6 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N6 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 N7 126.3(12) . . ?
C53 C52 C57 124.3(11) . . ?
N7 C52 C57 109.3(9) . . ?
C52 C53 C54 115.7(12) . . ?
C52 C53 H53 122.1 . . ?
C54 C53 H53 122.1 . . ?
C55 C54 C53 119.2(13) . . ?
C55 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?
C54 C55 C56 123.7(12) . . ?
C54 C55 H55 118.2 . . ?
C56 C55 H55 118.2 . . ?
C57 C56 C55 117.0(11) . . ?
C57 C56 H56 121.5 . . ?
C55 C56 H56 121.5 . . ?
C56 C57 C58 136.5(11) . . ?
C56 C57 C52 119.9(10) . . ?
C58 C57 C52 103.5(10) . . ?
C59 C58 C57 110.9(10) . . ?
C59 C58 C68 111.1(9) . . ?
C57 C58 C68 137.9(10) . . ?
C58 C59 N7 109.4(10) . . ?
C58 C59 C48 116.7(9) . . ?
N7 C59 C48 133.8(10) . . ?
C65 C60 C61 120.0(13) . . ?
C65 C60 H60 120.0 . . ?
C61 C60 H60 120.0 . . ?
C62 C61 C60 115.9(15) . . ?
C62 C61 H61 122.1 . . ?
C60 C61 H61 122.1 . . ?
C61 C62 C63 125.3(15) . . ?
C61 C62 H62 117.3 . . ?
C63 C62 H62 117.3 . . ?
C62 C63 C64 117.0(13) . . ?
C62 C63 H63 121.5 . . ?
C64 C63 H63 121.5 . . ?
C65 C64 C63 121.6(13) . . ?
C65 C64 H64 119.2 . . ?
C63 C64 H64 119.2 . . ?
C60 C65 C64 119.5(13) . . ?
C60 C65 C66 119.7(12) . . ?
C64 C65 C66 120.8(11) . . ?
N8 C66 C65 112.0(9) . . ?
N8 C66 H66A 109.2 . . ?
C65 C66 H66A 109.2 . . ?
N8 C66 H66B 109.2 . . ?
C65 C66 H66B 109.2 . . ?
H66A C66 H66B 107.9 . . ?
O6 C67 N8 127.9(10) . . ?
O6 C67 C68 124.4(9) . . ?
N8 C67 C68 107.6(9) . . ?
C58 C68 C67 116.8(8) . . ?
C58 C68 C69 113.1(8) . . ?
C67 C68 C69 99.8(8) . . ?
C58 C68 C49 103.5(8) . . ?
C67 C68 C49 109.2(8) . . ?
C69 C68 C49 114.8(8) . . ?
C74 C69 C70 121.8(11) . . ?
C74 C69 C68 108.1(10) . . ?
C70 C69 C68 130.0(10) . . ?
C71 C70 C69 119.2(11) . . ?
C71 C70 H70 120.4 . . ?
C69 C70 H70 120.4 . . ?
F2 C71 C70 122.1(10) . . ?
F2 C71 C72 116.9(10) . . ?
C70 C71 C72 120.9(11) . . ?
C73 C72 C71 120.4(11) . . ?
C73 C72 H72 119.8 . . ?
C71 C72 H72 119.8 . . ?
C72 C73 C74 116.4(11) . . ?
C72 C73 H73 121.8 . . ?
C74 C73 H73 121.8 . . ?
N8 C74 C69 112.0(10) . . ?
N8 C74 C73 126.8(11) . . ?
C69 C74 C73 121.3(11) . . ?
C9 N1 C2 107.3(10) . . ?
C9 N1 C1 126.7(13) . . ?
C2 N1 C1 126.0(12) . . ?
C10 N2 C13 111.5(10) . . ?
C10 N2 C14 122.4(10) . . ?
C13 N2 C14 125.9(10) . . ?
C22 N3 C15 111.2(11) . . ?
C22 N3 H3A 124.4 . . ?
C15 N3 H3A 124.4 . . ?
C30 N4 C29 126.7(11) . . ?
C30 N4 C37 110.1(9) . . ?
C29 N4 C37 123.0(10) . . ?
C46 N5 C39 108.4(9) . . ?
C46 N5 C38 125.7(11) . . ?
C39 N5 C38 125.8(10) . . ?
C47 N6 C50 113.8(10) . . ?
C47 N6 C51 122.4(10) . . ?
C50 N6 C51 123.8(11) . . ?
C59 N7 C52 106.8(10) . . ?
C59 N7 H7 126.6 . . ?
C52 N7 H7 126.6 . . ?
C74 N8 C67 112.4(9) . . ?
C74 N8 C66 126.5(10) . . ?
C67 N8 C66 121.1(9) . . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.074


####################################################################### 
# 
# 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_6k
_database_code_depnum_ccdc_archive 'CCDC 2177758'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H34 N4 O3, C3 H7 N O'
_chemical_formula_sum            'C43 H41 N5 O4'
_chemical_formula_weight         691.81

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

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

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

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

_cell_length_a                   11.3858(5)
_cell_length_b                   11.7752(5)
_cell_length_c                   15.6044(7)
_cell_angle_alpha                77.5323(13)
_cell_angle_beta                 83.5022(14)
_cell_angle_gamma                66.2724(12)
_cell_volume                     1869.26(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9449
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            26708
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.337
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7294
_reflns_number_gt                4983
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0754P)²+0.7436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7294
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0591(3) 0.8978(2) 0.2342(2) 0.0803(10) Uani 1 1 d . . . . .
H1A H -0.0173 0.9017 0.2110 0.120 Uiso 1 1 calc R U . . .
H1B H 0.0838 0.9634 0.2002 0.120 Uiso 1 1 calc R U . . .
H1C H 0.0428 0.9091 0.2942 0.120 Uiso 1 1 calc R U . . .
C2 C 0.2910(2) 0.74679(19) 0.23433(14) 0.0415(5) Uani 1 1 d . . . . .
C3 C 0.3544(3) 0.8243(2) 0.23990(16) 0.0541(7) Uani 1 1 d . . . . .
H3 H 0.3096 0.9098 0.2405 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4848(3) 0.7697(3) 0.2445(2) 0.0664(8) Uani 1 1 d . . . . .
H4 H 0.5298 0.8191 0.2482 0.080 Uiso 1 1 calc R U . . .
C5 C 0.5519(3) 0.6420(3) 0.2438(2) 0.0677(8) Uani 1 1 d . . . . .
H5 H 0.6409 0.6079 0.2468 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4903(2) 0.5650(2) 0.23869(17) 0.0526(6) Uani 1 1 d . . . . .
H6 H 0.5367 0.4796 0.2384 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3568(2) 0.61694(18) 0.23398(14) 0.0376(5) Uani 1 1 d . . . . .
C8 C 0.26078(19) 0.56818(17) 0.22976(13) 0.0335(5) Uani 1 1 d . . . . .
C9 C 0.1459(2) 0.66680(19) 0.22761(15) 0.0431(5) Uani 1 1 d . . . . .
H9 H 0.0671 0.6616 0.2248 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6360(2) 0.3043(2) 0.05570(15) 0.0515(6) Uani 1 1 d . . . . .
H10 H 0.5969 0.3920 0.0460 0.062 Uiso 1 1 calc R U . . .
C11 C 0.7402(3) 0.2448(3) 0.00386(18) 0.0745(9) Uani 1 1 d . . . . .
H11 H 0.7715 0.2924 -0.0410 0.089 Uiso 1 1 calc R U . . .
C12 C 0.7972(3) 0.1159(4) 0.0187(2) 0.0852(10) Uani 1 1 d . . . . .
H12 H 0.8675 0.0761 -0.0162 0.102 Uiso 1 1 calc R U . . .
C13 C 0.7517(3) 0.0442(3) 0.0847(2) 0.0749(9) Uani 1 1 d . . . . .
H13 H 0.7915 -0.0434 0.0944 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6469(2) 0.1023(2) 0.13651(17) 0.0534(6) Uani 1 1 d . . . . .
H14 H 0.6148 0.0545 0.1806 0.064 Uiso 1 1 calc R U . . .
C15 C 0.59072(19) 0.2328(2) 0.12168(14) 0.0371(5) Uani 1 1 d . . . . .
C16 C 0.37114(19) 0.39081(18) 0.14825(14) 0.0331(5) Uani 1 1 d . . . . .
C17 C 0.28519(19) 0.43317(17) 0.22833(13) 0.0309(4) Uani 1 1 d . . . . .
C18 C 0.36119(18) 0.33599(17) 0.30782(13) 0.0292(4) Uani 1 1 d . . . . .
H18 H 0.3723 0.3812 0.3501 0.035 Uiso 1 1 calc R U . . .
C19 C 0.49028(19) 0.26226(18) 0.26951(13) 0.0310(4) Uani 1 1 d . . . . .
C20 C 0.2734(5) -0.3542(4) 0.4868(3) 0.1348(19) Uani 1 1 d . . . . .
H20A H 0.2051 -0.3273 0.5294 0.202 Uiso 1 1 calc R U . . .
H20B H 0.3181 -0.4442 0.5009 0.202 Uiso 1 1 calc R U . . .
H20C H 0.2384 -0.3310 0.4295 0.202 Uiso 1 1 calc R U . . .
C21 C 0.3642(4) -0.2923(3) 0.4879(2) 0.0893(11) Uani 1 1 d . . . . .
H21A H 0.4339 -0.3219 0.4458 0.107 Uiso 1 1 calc R U . . .
H21B H 0.4006 -0.3182 0.5456 0.107 Uiso 1 1 calc R U . . .
C22 C 0.3032(3) -0.1483(2) 0.46628(17) 0.0552(7) Uani 1 1 d . . . . .
H22A H 0.2593 -0.1216 0.4112 0.066 Uiso 1 1 calc R U . . .
H22B H 0.2401 -0.1173 0.5118 0.066 Uiso 1 1 calc R U . . .
C23 C 0.4023(2) -0.09262(19) 0.45911(16) 0.0447(6) Uani 1 1 d . . . . .
H23A H 0.4441 -0.1182 0.5149 0.054 Uiso 1 1 calc R U . . .
H23B H 0.4670 -0.1271 0.4153 0.054 Uiso 1 1 calc R U . . .
C24 C 0.35538(19) 0.10973(18) 0.35290(13) 0.0316(5) Uani 1 1 d . . . . .
C25 C 0.28453(18) 0.25214(17) 0.35370(13) 0.0298(4) Uani 1 1 d . . . . .
C26 C 0.25421(18) 0.25201(18) 0.45057(13) 0.0306(4) Uani 1 1 d . . . . .
C27 C 0.19926(19) 0.3498(2) 0.49577(14) 0.0373(5) Uani 1 1 d . . . . .
H27 H 0.1737 0.4328 0.4657 0.045 Uiso 1 1 calc R U . . .
C28 C 0.1818(2) 0.3246(2) 0.58703(15) 0.0437(5) Uani 1 1 d . . . . .
C29 C 0.1234(3) 0.4311(3) 0.63760(18) 0.0644(7) Uani 1 1 d . . . . .
H29A H 0.0351 0.4783 0.6226 0.097 Uiso 1 1 calc R U . . .
H29B H 0.1695 0.4857 0.6230 0.097 Uiso 1 1 calc R U . . .
H29C H 0.1285 0.3972 0.6994 0.097 Uiso 1 1 calc R U . . .
C30 C 0.2204(2) 0.2001(2) 0.62920(15) 0.0503(6) Uani 1 1 d . . . . .
H30 H 0.2094 0.1829 0.6899 0.060 Uiso 1 1 calc R U . . .
C31 C 0.2751(2) 0.0994(2) 0.58502(15) 0.0472(6) Uani 1 1 d . . . . .
H31 H 0.2995 0.0163 0.6147 0.057 Uiso 1 1 calc R U . . .
C32 C 0.29167(19) 0.12809(19) 0.49522(13) 0.0348(5) Uani 1 1 d . . . . .
C33 C 0.16982(18) 0.40167(18) 0.23155(13) 0.0315(5) Uani 1 1 d . . . . .
C34 C 0.16915(18) 0.30560(18) 0.29699(13) 0.0310(4) Uani 1 1 d . . . . .
C35 C 0.05897(19) 0.28104(19) 0.28763(14) 0.0347(5) Uani 1 1 d . . . . .
C36 C 0.0063(2) 0.1950(2) 0.33257(16) 0.0461(6) Uani 1 1 d . . . . .
H36 H 0.0454 0.1364 0.3818 0.055 Uiso 1 1 calc R U . . .
C37 C -0.1044(2) 0.1991(3) 0.30238(19) 0.0574(7) Uani 1 1 d . . . . .
H37 H -0.1400 0.1421 0.3313 0.069 Uiso 1 1 calc R U . . .
C38 C -0.1638(2) 0.2867(3) 0.22940(19) 0.0606(7) Uani 1 1 d . . . . .
H38 H -0.2388 0.2870 0.2108 0.073 Uiso 1 1 calc R U . . .
C39 C -0.1159(2) 0.3729(2) 0.18365(17) 0.0528(6) Uani 1 1 d . . . . .
H39 H -0.1568 0.4312 0.1349 0.063 Uiso 1 1 calc R U . . .
C40 C -0.00335(19) 0.3695(2) 0.21337(14) 0.0377(5) Uani 1 1 d . . . . .
C1S C 0.1078(5) 0.2631(4) -0.0052(3) 0.1228(16) Uani 1 1 d . . . . .
H1S H 0.0494 0.2524 0.0392 0.147 Uiso 1 1 calc R U . . .
C2S C 0.2703(6) 0.1373(4) 0.0971(3) 0.1369(19) Uani 1 1 d . . . . .
H2S1 H 0.2004 0.1231 0.1315 0.205 Uiso 1 1 calc R U . . .
H2S2 H 0.3034 0.1814 0.1266 0.205 Uiso 1 1 calc R U . . .
H2S3 H 0.3370 0.0577 0.0899 0.205 Uiso 1 1 calc R U . . .
C3S C 0.3218(6) 0.2288(6) -0.0494(4) 0.168(2) Uani 1 1 d . . . . .
H3S1 H 0.3918 0.1493 -0.0520 0.252 Uiso 1 1 calc R U . . .
H3S2 H 0.3531 0.2855 -0.0332 0.252 Uiso 1 1 calc R U . . .
H3S3 H 0.2836 0.2643 -0.1058 0.252 Uiso 1 1 calc R U . . .
N1 N 0.16189(19) 0.77567(16) 0.23011(13) 0.0486(5) Uani 1 1 d . . . . .
N2 N 0.48562(15) 0.29309(14) 0.17797(11) 0.0319(4) Uani 1 1 d . . . . .
N3 N 0.35078(16) 0.04493(15) 0.43555(11) 0.0363(4) Uani 1 1 d . . . . .
N4 N 0.06705(16) 0.44214(16) 0.17946(12) 0.0387(4) Uani 1 1 d . . . . .
H4A H 0.0492 0.5017 0.1340 0.046 Uiso 1 1 calc R U . . .
N1S N 0.2271(3) 0.2095(2) 0.01512(16) 0.0708(7) Uani 1 1 d . . . . .
O1 O 0.34479(15) 0.43346(14) 0.07240(10) 0.0474(4) Uani 1 1 d . . . . .
O2 O 0.58450(14) 0.19085(13) 0.30994(10) 0.0413(4) Uani 1 1 d . . . . .
O3 O 0.40346(15) 0.06398(13) 0.28805(10) 0.0420(4) Uani 1 1 d . . . . .
O1S O 0.0630(4) 0.3248(3) -0.0738(2) 0.1677(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.453(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.375(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.407(3) . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.437(3) . ?
C8 C9 1.353(3) . ?
C8 C17 1.504(3) . ?
C9 N1 1.374(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.375(3) . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 N2 1.434(3) . ?
C16 O1 1.202(2) . ?
C16 N2 1.392(3) . ?
C16 C17 1.539(3) . ?
C17 C33 1.495(3) . ?
C17 C18 1.559(3) . ?
C18 C19 1.507(3) . ?
C18 C25 1.580(3) . ?
C18 H18 0.9800 . ?
C19 O2 1.206(2) . ?
C19 N2 1.397(3) . ?
C20 C21 1.488(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.526(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.500(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N3 1.459(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O3 1.219(2) . ?
C24 N3 1.356(3) . ?
C24 C25 1.543(3) . ?
C25 C34 1.504(3) . ?
C25 C26 1.512(3) . ?
C26 C27 1.373(3) . ?
C26 C32 1.387(3) . ?
C27 C28 1.399(3) . ?
C27 H27 0.9300 . ?
C28 C30 1.380(3) . ?
C28 C29 1.509(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(3) . ?
C31 H31 0.9300 . ?
C32 N3 1.414(3) . ?
C33 C34 1.352(3) . ?
C33 N4 1.362(3) . ?
C34 C35 1.425(3) . ?
C35 C36 1.402(3) . ?
C35 C40 1.415(3) . ?
C36 C37 1.374(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.387(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.372(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.394(3) . ?
C39 H39 0.9300 . ?
C40 N4 1.384(3) . ?
C1S O1S 1.193(5) . ?
C1S N1S 1.291(5) . ?
C1S H1S 0.9300 . ?
C2S N1S 1.392(4) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3S N1S 1.442(5) . ?
C3S H3S1 0.9600 . ?
C3S H3S2 0.9600 . ?
C3S H3S3 0.9600 . ?
N4 H4A 0.8600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.7(2) . . ?
N1 C2 C7 107.99(18) . . ?
C3 C2 C7 122.3(2) . . ?
C4 C3 C2 117.4(2) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 118.4(2) . . ?
C6 C7 C8 135.00(19) . . ?
C2 C7 C8 106.55(19) . . ?
C9 C8 C7 106.66(17) . . ?
C9 C8 C17 127.32(19) . . ?
C7 C8 C17 126.01(18) . . ?
C8 C9 N1 110.6(2) . . ?
C8 C9 H9 124.7 . . ?
N1 C9 H9 124.7 . . ?
C15 C10 C11 119.4(2) . . ?
C15 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C10 C15 C14 121.1(2) . . ?
C10 C15 N2 120.09(19) . . ?
C14 C15 N2 118.79(19) . . ?
O1 C16 N2 125.07(19) . . ?
O1 C16 C17 126.34(18) . . ?
N2 C16 C17 108.59(16) . . ?
C33 C17 C8 116.74(16) . . ?
C33 C17 C16 109.29(16) . . ?
C8 C17 C16 110.23(15) . . ?
C33 C17 C18 101.52(15) . . ?
C8 C17 C18 114.35(16) . . ?
C16 C17 C18 103.66(15) . . ?
C19 C18 C17 105.00(15) . . ?
C19 C18 C25 113.82(15) . . ?
C17 C18 C25 109.62(15) . . ?
C19 C18 H18 109.4 . . ?
C17 C18 H18 109.4 . . ?
C25 C18 H18 109.4 . . ?
O2 C19 N2 124.61(18) . . ?
O2 C19 C18 126.48(18) . . ?
N2 C19 C18 108.87(16) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 C21 C22 114.1(3) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 111.2(2) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N3 C23 C22 114.04(19) . . ?
N3 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
N3 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
O3 C24 N3 126.20(18) . . ?
O3 C24 C25 125.33(18) . . ?
N3 C24 C25 108.44(16) . . ?
C34 C25 C26 114.87(16) . . ?
C34 C25 C24 109.48(15) . . ?
C26 C25 C24 101.65(15) . . ?
C34 C25 C18 101.14(15) . . ?
C26 C25 C18 115.36(15) . . ?
C24 C25 C18 114.76(15) . . ?
C27 C26 C32 120.09(19) . . ?
C27 C26 C25 130.99(18) . . ?
C32 C26 C25 108.92(17) . . ?
C26 C27 C28 120.0(2) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C30 C28 C27 118.2(2) . . ?
C30 C28 C29 121.2(2) . . ?
C27 C28 C29 120.5(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 122.9(2) . . ?
C28 C30 H30 118.5 . . ?
C31 C30 H30 118.5 . . ?
C32 C31 C30 117.1(2) . . ?
C32 C31 H31 121.4 . . ?
C30 C31 H31 121.4 . . ?
C31 C32 C26 121.6(2) . . ?
C31 C32 N3 128.74(19) . . ?
C26 C32 N3 109.60(17) . . ?
C34 C33 N4 110.99(17) . . ?
C34 C33 C17 114.37(17) . . ?
N4 C33 C17 134.46(18) . . ?
C33 C34 C35 107.72(18) . . ?
C33 C34 C25 113.34(17) . . ?
C35 C34 C25 138.82(17) . . ?
C36 C35 C40 119.3(2) . . ?
C36 C35 C34 135.4(2) . . ?
C40 C35 C34 105.27(17) . . ?
C37 C36 C35 118.6(2) . . ?
C37 C36 H36 120.7 . . ?
C35 C36 H36 120.7 . . ?
C36 C37 C38 121.1(2) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C39 C38 C37 122.3(2) . . ?
C39 C38 H38 118.9 . . ?
C37 C38 H38 118.9 . . ?
C38 C39 C40 117.2(2) . . ?
C38 C39 H39 121.4 . . ?
C40 C39 H39 121.4 . . ?
N4 C40 C39 129.6(2) . . ?
N4 C40 C35 108.81(18) . . ?
C39 C40 C35 121.5(2) . . ?
O1S C1S N1S 128.2(5) . . ?
O1S C1S H1S 115.9 . . ?
N1S C1S H1S 115.9 . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
N1S C3S H3S1 109.5 . . ?
N1S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
N1S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
C9 N1 C2 108.21(17) . . ?
C9 N1 C1 125.5(2) . . ?
C2 N1 C1 126.1(2) . . ?
C16 N2 C19 112.89(16) . . ?
C16 N2 C15 124.26(17) . . ?
C19 N2 C15 122.80(16) . . ?
C24 N3 C32 111.09(16) . . ?
C24 N3 C23 123.95(17) . . ?
C32 N3 C23 124.96(17) . . ?
C33 N4 C40 107.20(17) . . ?
C33 N4 H4A 126.4 . . ?
C40 N4 H4A 126.4 . . ?
C1S N1S C2S 124.0(4) . . ?
C1S N1S C3S 118.5(4) . . ?
C2S N1S C3S 117.5(4) . . ?

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
N4 H4A O1S 0.86 2.01 2.788(3) 150.3 2_565

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.049

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

data_8e
_database_code_depnum_ccdc_archive 'CCDC 2177760'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H25 N3 O4'
_chemical_formula_sum            'C37 H25 N3 O4'
_chemical_formula_weight         575.60

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

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

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

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

_cell_length_a                   12.284(3)
_cell_length_b                   12.500(3)
_cell_length_c                   15.924(3)
_cell_angle_alpha                74.639(7)
_cell_angle_beta                 86.466(7)
_cell_angle_gamma                65.105(6)
_cell_volume                     2135.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7341
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      23.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.895
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            30584
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8361
_reflns_number_gt                4531
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0973P)²+0.7599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8361
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2192
_refine_ls_wR_factor_gt          0.1902
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2763(3) 0.6000(4) 0.3681(3) 0.0883(12) Uani 1 1 d . . . . .
H1A H 1.3189 0.6082 0.4128 0.132 Uiso 1 1 calc R U . . .
H1B H 1.3147 0.6106 0.3141 0.132 Uiso 1 1 calc R U . . .
H1C H 1.2767 0.5202 0.3844 0.132 Uiso 1 1 calc R U . . .
C2 C 1.1164(2) 0.8167(3) 0.33309(18) 0.0514(7) Uani 1 1 d . . . . .
C3 C 1.1857(3) 0.8836(4) 0.3129(2) 0.0632(9) Uani 1 1 d . . . . .
H3 H 1.2692 0.8449 0.3144 0.076 Uiso 1 1 calc R U . . .
C4 C 1.1267(3) 1.0067(4) 0.2911(2) 0.0738(10) Uani 1 1 d . . . . .
H4 H 1.1707 1.0535 0.2780 0.089 Uiso 1 1 calc R U . . .
C5 C 1.0005(3) 1.0661(3) 0.2876(2) 0.0757(10) Uani 1 1 d . . . . .
H5 H 0.9627 1.1511 0.2715 0.091 Uiso 1 1 calc R U . . .
C6 C 0.9323(3) 1.0007(3) 0.3077(2) 0.0591(8) Uani 1 1 d . . . . .
H6 H 0.8489 1.0406 0.3057 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9907(2) 0.8724(3) 0.33143(17) 0.0437(7) Uani 1 1 d . . . . .
C8 C 0.9524(2) 0.7756(2) 0.35552(17) 0.0421(6) Uani 1 1 d . . . . .
C9 C 1.0533(2) 0.6694(3) 0.37092(19) 0.0528(8) Uani 1 1 d . . . . .
H9 H 1.0543 0.5918 0.3882 0.063 Uiso 1 1 calc R U . . .
C10 C 0.8194(2) 0.6680(2) 0.40972(19) 0.0425(7) Uani 1 1 d . . . . .
C11 C 0.8228(2) 0.7881(2) 0.35797(17) 0.0399(6) Uani 1 1 d . . . . .
C12 C 0.7650(2) 0.8124(2) 0.26581(17) 0.0435(7) Uani 1 1 d . . . . .
H12 H 0.8196 0.8243 0.2205 0.052 Uiso 1 1 calc R U . . .
C13 C 0.7503(2) 0.6984(3) 0.2692(2) 0.0502(7) Uani 1 1 d . . . . .
C14 C 0.7619(3) 0.5119(3) 0.38060(19) 0.0493(7) Uani 1 1 d . . . . .
C15 C 0.6493(3) 0.5168(3) 0.3759(2) 0.0724(10) Uani 1 1 d . . . . .
H15 H 0.5832 0.5917 0.3581 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6348(4) 0.4099(4) 0.3979(3) 0.0969(14) Uani 1 1 d . . . . .
H16 H 0.5587 0.4123 0.3931 0.116 Uiso 1 1 calc R U . . .
C17 C 0.7312(4) 0.3000(4) 0.4269(3) 0.0883(12) Uani 1 1 d . . . . .
H17 H 0.7205 0.2280 0.4426 0.106 Uiso 1 1 calc R U . . .
C18 C 0.8421(3) 0.2960(3) 0.4326(3) 0.0767(10) Uani 1 1 d . . . . .
H18 H 0.9079 0.2212 0.4521 0.092 Uiso 1 1 calc R U . . .
C19 C 0.8585(3) 0.4024(3) 0.4098(2) 0.0610(8) Uani 1 1 d . . . . .
H19 H 0.9348 0.3995 0.4142 0.073 Uiso 1 1 calc R U . . .
C20 C 0.8141(3) 0.8782(3) 0.5357(2) 0.0643(9) Uani 1 1 d . . . . .
H20A H 0.8774 0.8037 0.5285 0.096 Uiso 1 1 calc R U . . .
H20B H 0.7742 0.8606 0.5879 0.096 Uiso 1 1 calc R U . . .
H20C H 0.8473 0.9337 0.5401 0.096 Uiso 1 1 calc R U . . .
C21 C 0.6224(2) 1.0396(2) 0.45058(19) 0.0471(7) Uani 1 1 d . . . . .
C22 C 0.5735(3) 1.1116(3) 0.5094(2) 0.0576(8) Uani 1 1 d . . . . .
H22 H 0.6119 1.0925 0.5633 0.069 Uiso 1 1 calc R U . . .
C23 C 0.4657(3) 1.2117(3) 0.4832(3) 0.0678(10) Uani 1 1 d . . . . .
H23 H 0.4310 1.2626 0.5198 0.081 Uiso 1 1 calc R U . . .
C24 C 0.4072(3) 1.2386(3) 0.4032(3) 0.0699(10) Uani 1 1 d . . . . .
H24 H 0.3342 1.3069 0.3878 0.084 Uiso 1 1 calc R U . . .
C25 C 0.4539(3) 1.1678(3) 0.3471(2) 0.0607(8) Uani 1 1 d . . . . .
H25 H 0.4133 1.1872 0.2940 0.073 Uiso 1 1 calc R U . . .
C26 C 0.5638(2) 1.0653(2) 0.37009(19) 0.0466(7) Uani 1 1 d . . . . .
C27 C 0.6390(2) 0.9701(2) 0.33177(17) 0.0429(7) Uani 1 1 d . . . . .
C28 C 0.7342(2) 0.8943(2) 0.38811(17) 0.0393(6) Uani 1 1 d . . . . .
C29 C 0.6426(2) 0.9291(2) 0.25008(17) 0.0441(7) Uani 1 1 d . . . . .
C30 C 0.6385(3) 1.0264(3) 0.16625(19) 0.0527(7) Uani 1 1 d . . . . .
C31 C 0.5250(3) 1.0654(3) 0.11559(18) 0.0533(8) Uani 1 1 d . . . . .
C32 C 0.4827(3) 1.1529(3) 0.0369(2) 0.0769(10) Uani 1 1 d . . . . .
H32 H 0.5245 1.1982 0.0089 0.092 Uiso 1 1 calc R U . . .
C33 C 0.3729(4) 1.1691(4) 0.0018(3) 0.0973(14) Uani 1 1 d . . . . .
H33 H 0.3416 1.2265 -0.0513 0.117 Uiso 1 1 calc R U . . .
C34 C 0.3102(4) 1.1035(4) 0.0429(3) 0.0972(13) Uani 1 1 d . . . . .
H34 H 0.2377 1.1170 0.0178 0.117 Uiso 1 1 calc R U . . .
C35 C 0.3552(3) 1.0173(4) 0.1219(2) 0.0787(11) Uani 1 1 d . . . . .
H35 H 0.3132 0.9726 0.1506 0.094 Uiso 1 1 calc R U . . .
C36 C 0.4620(3) 0.9991(3) 0.15683(19) 0.0545(8) Uani 1 1 d . . . . .
C37 C 0.5283(2) 0.9101(3) 0.23880(18) 0.0474(7) Uani 1 1 d . . . . .
N1 N 1.1531(2) 0.6923(2) 0.35744(17) 0.0601(7) Uani 1 1 d . . . . .
N2 N 0.77789(19) 0.6229(2) 0.35432(15) 0.0459(6) Uani 1 1 d . . . . .
N3 N 0.7283(2) 0.9333(2) 0.46113(15) 0.0453(6) Uani 1 1 d . . . . .
O1 O 0.84745(18) 0.61899(18) 0.48603(13) 0.0551(5) Uani 1 1 d . . . . .
O2 O 0.7180(2) 0.6739(2) 0.20931(15) 0.0714(6) Uani 1 1 d . . . . .
O3 O 0.7162(2) 1.0611(2) 0.14568(16) 0.0855(8) Uani 1 1 d . . . . .
O4 O 0.49878(18) 0.8375(2) 0.28910(14) 0.0658(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.452(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.373(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.351(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(4) . ?
C8 C9 1.356(4) . ?
C8 C11 1.532(3) . ?
C9 N1 1.364(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.204(3) . ?
C10 N2 1.384(3) . ?
C10 C11 1.526(4) . ?
C11 C28 1.495(4) . ?
C11 C12 1.569(4) . ?
C12 C13 1.496(4) . ?
C12 C29 1.568(4) . ?
C12 H12 0.9800 . ?
C13 O2 1.211(3) . ?
C13 N2 1.397(4) . ?
C14 C19 1.364(4) . ?
C14 C15 1.364(4) . ?
C14 N2 1.433(3) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N3 1.450(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.393(3) . ?
C21 C26 1.402(4) . ?
C21 C22 1.403(4) . ?
C22 C23 1.375(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.426(4) . ?
C27 C28 1.348(4) . ?
C27 C29 1.511(4) . ?
C28 N3 1.361(3) . ?
C29 C30 1.537(4) . ?
C29 C37 1.547(4) . ?
C30 O3 1.199(3) . ?
C30 C31 1.481(4) . ?
C31 C36 1.380(4) . ?
C31 C32 1.382(4) . ?
C32 C33 1.405(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.384(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.362(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.484(4) . ?
C37 O4 1.206(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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.1(3) . . ?
N1 C2 C7 108.3(2) . . ?
C3 C2 C7 122.6(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 118.5(3) . . ?
C2 C7 C8 106.4(2) . . ?
C6 C7 C8 135.1(3) . . ?
C9 C8 C7 106.8(2) . . ?
C9 C8 C11 126.1(2) . . ?
C7 C8 C11 127.1(2) . . ?
C8 C9 N1 110.4(3) . . ?
C8 C9 H9 124.8 . . ?
N1 C9 H9 124.8 . . ?
O1 C10 N2 124.7(2) . . ?
O1 C10 C11 126.6(3) . . ?
N2 C10 C11 108.7(2) . . ?
C28 C11 C10 111.8(2) . . ?
C28 C11 C8 115.3(2) . . ?
C10 C11 C8 110.2(2) . . ?
C28 C11 C12 101.4(2) . . ?
C10 C11 C12 103.9(2) . . ?
C8 C11 C12 113.4(2) . . ?
C13 C12 C29 113.0(2) . . ?
C13 C12 C11 104.6(2) . . ?
C29 C12 C11 109.2(2) . . ?
C13 C12 H12 110.0 . . ?
C29 C12 H12 110.0 . . ?
C11 C12 H12 110.0 . . ?
O2 C13 N2 124.1(3) . . ?
O2 C13 C12 126.7(3) . . ?
N2 C13 C12 109.2(2) . . ?
C19 C14 C15 120.4(3) . . ?
C19 C14 N2 120.3(2) . . ?
C15 C14 N2 119.3(3) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.6(3) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C26 109.3(2) . . ?
N3 C21 C22 128.3(3) . . ?
C26 C21 C22 122.3(3) . . ?
C23 C22 C21 116.5(3) . . ?
C23 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 121.7(3) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 119.1(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 118.7(3) . . ?
C25 C26 C27 136.1(3) . . ?
C21 C26 C27 105.3(2) . . ?
C28 C27 C26 107.7(2) . . ?
C28 C27 C29 112.8(2) . . ?
C26 C27 C29 139.6(2) . . ?
C27 C28 N3 111.4(2) . . ?
C27 C28 C11 114.7(2) . . ?
N3 C28 C11 133.9(2) . . ?
C27 C29 C30 113.0(2) . . ?
C27 C29 C37 110.3(2) . . ?
C30 C29 C37 103.4(2) . . ?
C27 C29 C12 101.8(2) . . ?
C30 C29 C12 112.2(2) . . ?
C37 C29 C12 116.5(2) . . ?
O3 C30 C31 127.0(3) . . ?
O3 C30 C29 125.1(3) . . ?
C31 C30 C29 107.9(2) . . ?
C36 C31 C32 121.6(3) . . ?
C36 C31 C30 110.5(2) . . ?
C32 C31 C30 127.9(3) . . ?
C31 C32 C33 115.9(4) . . ?
C31 C32 H32 122.0 . . ?
C33 C32 H32 122.0 . . ?
C34 C33 C32 122.5(4) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 C34 C35 119.8(4) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 118.8(4) . . ?
C36 C35 H35 120.6 . . ?
C34 C35 H35 120.6 . . ?
C35 C36 C31 121.4(3) . . ?
C35 C36 C37 128.1(3) . . ?
C31 C36 C37 110.5(2) . . ?
O4 C37 C36 127.1(3) . . ?
O4 C37 C29 125.4(2) . . ?
C36 C37 C29 107.5(2) . . ?
C9 N1 C2 108.1(2) . . ?
C9 N1 C1 125.4(3) . . ?
C2 N1 C1 126.5(3) . . ?
C10 N2 C13 113.1(2) . . ?
C10 N2 C14 124.3(2) . . ?
C13 N2 C14 122.7(2) . . ?
C28 N3 C21 106.4(2) . . ?
C28 N3 C20 128.0(2) . . ?
C21 N3 C20 125.6(2) . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045


####################################################################### 
# 
# 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_8b
_database_code_depnum_ccdc_archive 'CCDC 2177759'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H23 N3 O4, C3 H7 N O'
_chemical_formula_sum            'C39 H30 N4 O5'
_chemical_formula_weight         634.67

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

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

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

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

_cell_length_a                   10.131(2)
_cell_length_b                   11.507(3)
_cell_length_c                   15.601(4)
_cell_angle_alpha                72.289(7)
_cell_angle_beta                 86.070(8)
_cell_angle_gamma                68.259(7)
_cell_volume                     1607.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8588
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   0.6875
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            22885
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6284
_reflns_number_gt                4280
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0715P)²+0.5482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6284
_refine_ls_number_parameters     436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1889(2) -0.0545(2) 0.39220(18) 0.0630(7) Uani 1 1 d . . . . .
H1A H 1.1833 -0.1339 0.3877 0.095 Uiso 1 1 calc R U . . .
H1B H 1.2289 -0.0704 0.4506 0.095 Uiso 1 1 calc R U . . .
H1C H 1.2483 -0.0258 0.3466 0.095 Uiso 1 1 calc R U . . .
C2 C 1.0046(2) 0.1563(2) 0.40707(13) 0.0414(5) Uani 1 1 d . . . . .
C3 C 1.0810(2) 0.1971(2) 0.45470(15) 0.0538(6) Uani 1 1 d . . . . .
H3 H 1.1761 0.1480 0.4728 0.065 Uiso 1 1 calc R U . . .
C4 C 1.0107(3) 0.3123(3) 0.47379(17) 0.0656(7) Uani 1 1 d . . . . .
H4 H 1.0596 0.3428 0.5047 0.079 Uiso 1 1 calc R U . . .
C5 C 0.8677(3) 0.3851(3) 0.44812(18) 0.0678(7) Uani 1 1 d . . . . .
H5 H 0.8227 0.4622 0.4633 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7917(2) 0.3459(2) 0.40104(16) 0.0538(6) Uani 1 1 d . . . . .
H6 H 0.6964 0.3960 0.3839 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8597(2) 0.2295(2) 0.37913(13) 0.0396(5) Uani 1 1 d . . . . .
C8 C 0.8173(2) 0.15851(18) 0.33236(12) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.9341(2) 0.0499(2) 0.33484(14) 0.0442(5) Uani 1 1 d . . . . .
H9 H 0.9366 -0.0141 0.3093 0.053 Uiso 1 1 calc R U . . .
C10 C 0.67531(19) 0.08539(19) 0.25406(13) 0.0366(4) Uani 1 1 d . . . . .
C11 C 0.67511(19) 0.19988(18) 0.28449(12) 0.0347(4) Uani 1 1 d . . . . .
C12 C 0.54161(19) 0.22474(18) 0.34310(12) 0.0344(4) Uani 1 1 d . . . . .
H12 H 0.5641 0.2371 0.3990 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5074(2) 0.10321(18) 0.36351(12) 0.0357(4) Uani 1 1 d . . . . .
C14 C 0.5672(2) -0.08571(18) 0.30354(13) 0.0377(5) Uani 1 1 d . . . . .
C15 C 0.5370(3) -0.0921(2) 0.22078(15) 0.0535(6) Uani 1 1 d . . . . .
H15 H 0.5313 -0.0237 0.1688 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5151(3) -0.2014(2) 0.21600(17) 0.0647(7) Uani 1 1 d . . . . .
H16 H 0.4963 -0.2074 0.1603 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5209(3) -0.3009(2) 0.29228(18) 0.0635(7) Uani 1 1 d . . . . .
H17 H 0.5056 -0.3740 0.2884 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5493(3) -0.2934(2) 0.37505(17) 0.0580(6) Uani 1 1 d . . . . .
H18 H 0.5514 -0.3606 0.4270 0.070 Uiso 1 1 calc R U . . .
C19 C 0.5746(2) -0.1864(2) 0.38106(14) 0.0460(5) Uani 1 1 d . . . . .
H19 H 0.5963 -0.1820 0.4367 0.055 Uiso 1 1 calc R U . . .
C20 C 0.6024(2) 0.5047(2) 0.09479(13) 0.0454(5) Uani 1 1 d . . . . .
C21 C 0.6207(3) 0.5963(2) 0.01757(14) 0.0587(6) Uani 1 1 d . . . . .
H21 H 0.7081 0.5824 -0.0089 0.070 Uiso 1 1 calc R U . . .
C22 C 0.5043(4) 0.7081(2) -0.01772(16) 0.0679(8) Uani 1 1 d . . . . .
H22 H 0.5134 0.7714 -0.0690 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3730(3) 0.7293(2) 0.02110(16) 0.0650(7) Uani 1 1 d . . . . .
H23 H 0.2962 0.8055 -0.0056 0.078 Uiso 1 1 calc R U . . .
C24 C 0.3539(3) 0.6404(2) 0.09798(15) 0.0541(6) Uani 1 1 d . . . . .
H24 H 0.2659 0.6565 0.1239 0.065 Uiso 1 1 calc R U . . .
C25 C 0.4704(2) 0.52494(19) 0.13638(13) 0.0420(5) Uani 1 1 d . . . . .
C26 C 0.4956(2) 0.40927(18) 0.21148(12) 0.0375(5) Uani 1 1 d . . . . .
C27 C 0.6318(2) 0.32787(19) 0.21084(12) 0.0366(4) Uani 1 1 d . . . . .
C28 C 0.4175(2) 0.34965(18) 0.28719(12) 0.0358(4) Uani 1 1 d . . . . .
C29 C 0.2963(2) 0.3283(2) 0.24664(13) 0.0418(5) Uani 1 1 d . . . . .
C30 C 0.1621(2) 0.4339(2) 0.25373(15) 0.0502(6) Uani 1 1 d . . . . .
C31 C 0.0277(3) 0.4654(3) 0.21747(19) 0.0739(8) Uani 1 1 d . . . . .
H31 H 0.0115 0.4162 0.1848 0.089 Uiso 1 1 calc R U . . .
C32 C -0.0807(3) 0.5717(4) 0.2314(2) 0.0990(11) Uani 1 1 d . . . . .
H32 H -0.1721 0.5940 0.2085 0.119 Uiso 1 1 calc R U . . .
C33 C -0.0569(3) 0.6459(4) 0.2787(2) 0.0991(11) Uani 1 1 d . . . . .
H33 H -0.1319 0.7192 0.2851 0.119 Uiso 1 1 calc R U . . .
C34 C 0.0764(3) 0.6140(3) 0.31712(18) 0.0736(8) Uani 1 1 d . . . . .
H34 H 0.0917 0.6631 0.3503 0.088 Uiso 1 1 calc R U . . .
C35 C 0.1856(2) 0.5058(2) 0.30395(14) 0.0498(5) Uani 1 1 d . . . . .
C36 C 0.3360(2) 0.44640(19) 0.33887(14) 0.0426(5) Uani 1 1 d . . . . .
N1 N 1.04704(17) 0.04653(17) 0.37946(12) 0.0460(4) Uani 1 1 d . . . . .
N2 N 0.58834(16) 0.02804(15) 0.30966(10) 0.0364(4) Uani 1 1 d . . . . .
N3 N 0.69978(19) 0.38362(16) 0.14187(11) 0.0437(4) Uani 1 1 d . . . . .
H3A H 0.7873 0.3498 0.1298 0.052 Uiso 1 1 calc R U . . .
O1 O 0.74226(15) 0.04651(14) 0.19492(10) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.42167(15) 0.07606(14) 0.41490(9) 0.0480(4) Uani 1 1 d . . . . .
O3 O 0.31169(17) 0.24346(15) 0.21256(11) 0.0587(4) Uani 1 1 d . . . . .
O4 O 0.38702(17) 0.46833(15) 0.39687(10) 0.0585(4) Uani 1 1 d . . . . .
C37 C 0.0604(5) 0.2792(6) 0.0245(3) 0.1313(16) Uani 1 1 d . . . . .
H37 H 0.0888 0.3361 -0.0224 0.158 Uiso 1 1 calc R U . . .
C38 C 0.2525(6) 0.1062(5) -0.0136(4) 0.163(2) Uani 1 1 d . . . . .
H38A H 0.2795 0.1776 -0.0488 0.244 Uiso 1 1 calc R U . . .
H38B H 0.2283 0.0663 -0.0529 0.244 Uiso 1 1 calc R U . . .
H38C H 0.3304 0.0423 0.0270 0.244 Uiso 1 1 calc R U . . .
C39 C 0.1040(9) 0.0741(8) 0.1154(6) 0.291(5) Uani 1 1 d . . . . .
H39A H 0.1915 0.0173 0.1496 0.437 Uiso 1 1 calc R U . . .
H39B H 0.0582 0.0221 0.1012 0.437 Uiso 1 1 calc R U . . .
H39C H 0.0426 0.1266 0.1502 0.437 Uiso 1 1 calc R U . . .
N4 N 0.1322(4) 0.1547(4) 0.0367(2) 0.1122(10) Uani 1 1 d . . . . .
O5 O -0.0371(3) 0.3309(3) 0.0651(2) 0.1415(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.455(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.367(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.415(3) . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.432(3) . ?
C8 C9 1.358(3) . ?
C8 C11 1.511(3) . ?
C9 N1 1.362(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.205(2) . ?
C10 N2 1.393(2) . ?
C10 C11 1.530(3) . ?
C11 C27 1.498(3) . ?
C11 C12 1.565(2) . ?
C12 C13 1.500(3) . ?
C12 C28 1.567(3) . ?
C12 H12 0.9800 . ?
C13 O2 1.203(2) . ?
C13 N2 1.396(2) . ?
C14 C15 1.377(3) . ?
C14 C19 1.381(3) . ?
C14 N2 1.433(2) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N3 1.383(3) . ?
C20 C21 1.393(3) . ?
C20 C25 1.416(3) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.403(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.432(3) . ?
C26 C27 1.352(3) . ?
C26 C28 1.507(3) . ?
C27 N3 1.360(2) . ?
C28 C36 1.531(3) . ?
C28 C29 1.547(3) . ?
C29 O3 1.205(2) . ?
C29 C30 1.475(3) . ?
C30 C31 1.386(3) . ?
C30 C35 1.386(3) . ?
C31 C32 1.373(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.389(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.386(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.483(3) . ?
C36 O4 1.204(2) . ?
N3 H3A 0.8600 . ?
C37 O5 1.199(4) . ?
C37 N4 1.304(5) . ?
C37 H37 0.9300 . ?
C38 N4 1.430(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 N4 1.380(6) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.79(19) . . ?
N1 C2 C7 108.04(17) . . ?
C3 C2 C7 122.2(2) . . ?
C4 C3 C2 117.3(2) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 118.55(19) . . ?
C6 C7 C8 134.88(19) . . ?
C2 C7 C8 106.57(18) . . ?
C9 C8 C7 105.92(17) . . ?
C9 C8 C11 126.73(18) . . ?
C7 C8 C11 127.24(17) . . ?
C8 C9 N1 111.43(18) . . ?
C8 C9 H9 124.3 . . ?
N1 C9 H9 124.3 . . ?
O1 C10 N2 124.84(18) . . ?
O1 C10 C11 127.02(17) . . ?
N2 C10 C11 108.08(15) . . ?
C27 C11 C8 115.19(16) . . ?
C27 C11 C10 113.64(15) . . ?
C8 C11 C10 107.76(15) . . ?
C27 C11 C12 100.61(14) . . ?
C8 C11 C12 116.55(15) . . ?
C10 C11 C12 102.47(14) . . ?
C13 C12 C11 105.09(15) . . ?
C13 C12 C28 112.02(15) . . ?
C11 C12 C28 108.70(14) . . ?
C13 C12 H12 110.3 . . ?
C11 C12 H12 110.3 . . ?
C28 C12 H12 110.3 . . ?
O2 C13 N2 125.20(18) . . ?
O2 C13 C12 126.51(18) . . ?
N2 C13 C12 108.24(16) . . ?
C15 C14 C19 120.80(19) . . ?
C15 C14 N2 119.68(18) . . ?
C19 C14 N2 119.51(18) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
N3 C20 C21 128.8(2) . . ?
N3 C20 C25 109.02(17) . . ?
C21 C20 C25 122.1(2) . . ?
C22 C21 C20 117.1(2) . . ?
C22 C21 H21 121.5 . . ?
C20 C21 H21 121.5 . . ?
C21 C22 C23 121.8(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 121.7(2) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 118.3(2) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C24 C25 C20 118.94(19) . . ?
C24 C25 C26 136.3(2) . . ?
C20 C25 C26 104.71(18) . . ?
C27 C26 C25 108.02(17) . . ?
C27 C26 C28 111.86(16) . . ?
C25 C26 C28 140.07(18) . . ?
C26 C27 N3 110.76(17) . . ?
C26 C27 C11 114.95(16) . . ?
N3 C27 C11 134.29(18) . . ?
C26 C28 C36 111.51(16) . . ?
C26 C28 C29 108.90(15) . . ?
C36 C28 C29 102.37(16) . . ?
C26 C28 C12 101.72(15) . . ?
C36 C28 C12 114.99(15) . . ?
C29 C28 C12 117.50(15) . . ?
O3 C29 C30 127.2(2) . . ?
O3 C29 C28 125.41(18) . . ?
C30 C29 C28 107.32(17) . . ?
C31 C30 C35 121.1(2) . . ?
C31 C30 C29 128.8(2) . . ?
C35 C30 C29 110.18(19) . . ?
C32 C31 C30 117.8(3) . . ?
C32 C31 H31 121.1 . . ?
C30 C31 H31 121.1 . . ?
C31 C32 C33 121.3(3) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C32 C33 C34 121.6(3) . . ?
C32 C33 H33 119.2 . . ?
C34 C33 H33 119.2 . . ?
C35 C34 C33 117.1(3) . . ?
C35 C34 H34 121.4 . . ?
C33 C34 H34 121.4 . . ?
C30 C35 C34 121.0(2) . . ?
C30 C35 C36 109.80(19) . . ?
C34 C35 C36 129.2(2) . . ?
O4 C36 C35 127.49(19) . . ?
O4 C36 C28 125.31(19) . . ?
C35 C36 C28 107.20(18) . . ?
C9 N1 C2 108.04(16) . . ?
C9 N1 C1 125.47(19) . . ?
C2 N1 C1 126.46(18) . . ?
C10 N2 C13 112.96(15) . . ?
C10 N2 C14 123.95(15) . . ?
C13 N2 C14 122.49(16) . . ?
C27 N3 C20 107.46(17) . . ?
C27 N3 H3A 126.3 . . ?
C20 N3 H3A 126.3 . . ?
O5 C37 N4 129.2(5) . . ?
O5 C37 H37 115.4 . . ?
N4 C37 H37 115.4 . . ?
N4 C38 H38A 109.5 . . ?
N4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N4 C39 H39A 109.5 . . ?
N4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 N4 C39 113.8(5) . . ?
C37 N4 C38 123.3(4) . . ?
C39 N4 C38 121.3(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O5 0.86 1.96 2.778(3) 159.1 1_655

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045

