# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1937485'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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         'C34 H26 N4 O2, C2 H6 O '
_chemical_formula_sum            'C36 H32 N4 O3'
_chemical_formula_weight         568.65

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

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

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

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

_cell_length_a                   9.5972(6)
_cell_length_b                   11.9696(8)
_cell_length_c                   14.6218(9)
_cell_angle_alpha                104.321(2)
_cell_angle_beta                 91.690(2)
_cell_angle_gamma                113.084(2)
_cell_volume                     1482.01(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6772
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_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  0.979
_exptl_absorpt_correction_T_max  0.984
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23379
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6820
_reflns_number_gt                4104
_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)+(0.0686P)²+0.4944P] 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         6820
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.6377(2) 0.49867(19) 0.23486(14) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.6691(3) 0.6124(2) 0.21578(17) 0.0485(6) Uani 1 1 d . . . . .
H2 H 0.7579 0.6837 0.2449 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5637(3) 0.6165(2) 0.15180(17) 0.0523(6) Uani 1 1 d . . . . .
H3 H 0.5822 0.6919 0.1372 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4324(3) 0.5113(2) 0.10940(16) 0.0462(6) Uani 1 1 d . . . . .
H4 H 0.3632 0.5165 0.0665 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4013(2) 0.39710(19) 0.12958(14) 0.0367(5) Uani 1 1 d . . . . .
H5 H 0.3114 0.3264 0.1014 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5062(2) 0.39065(17) 0.19210(13) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.5103(2) 0.28433(18) 0.22810(13) 0.0299(4) Uani 1 1 d . . . . .
C8 C 0.6553(2) 0.3513(2) 0.30260(14) 0.0352(5) Uani 1 1 d . . . . .
C9 C 0.5300(2) 0.17514(18) 0.15302(14) 0.0334(5) Uani 1 1 d . . . . .
H9 H 0.5617 0.1300 0.1911 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6564(2) 0.21536(18) 0.09298(14) 0.0337(5) Uani 1 1 d . . . . .
C11 C 0.7944(3) 0.2139(2) 0.12037(17) 0.0500(6) Uani 1 1 d . . . . .
H11 H 0.8050 0.1866 0.1733 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9173(3) 0.2523(3) 0.07094(18) 0.0570(7) Uani 1 1 d . . . . .
H12 H 1.0090 0.2510 0.0918 0.068 Uiso 1 1 calc R U . . .
C13 C 0.9069(2) 0.2923(2) -0.00844(16) 0.0431(5) Uani 1 1 d . . . . .
C14 C 1.0400(3) 0.3345(3) -0.06294(19) 0.0609(7) Uani 1 1 d . . . . .
H14A H 1.0897 0.4252 -0.0443 0.091 Uiso 1 1 calc R U . . .
H14B H 1.0036 0.3041 -0.1301 0.091 Uiso 1 1 calc R U . . .
H14C H 1.1115 0.3009 -0.0491 0.091 Uiso 1 1 calc R U . . .
C15 C 0.7689(3) 0.2937(2) -0.03583(16) 0.0472(6) Uani 1 1 d . . . . .
H15 H 0.7579 0.3196 -0.0895 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6464(3) 0.2576(2) 0.01431(16) 0.0442(5) Uani 1 1 d . . . . .
H16 H 0.5560 0.2619 -0.0053 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3661(2) 0.20538(17) 0.26469(13) 0.0299(4) Uani 1 1 d . . . . .
H17 H 0.3934 0.1568 0.3015 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2770(2) 0.26938(18) 0.32194(13) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.3494(2) 0.39001(19) 0.38506(14) 0.0374(5) Uani 1 1 d . . . . .
H19 H 0.4547 0.4342 0.3895 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2676(3) 0.4451(2) 0.44111(15) 0.0445(5) Uani 1 1 d . . . . .
H20 H 0.3176 0.5253 0.4836 0.053 Uiso 1 1 calc R U . . .
C21 C 0.1117(3) 0.3808(2) 0.43382(17) 0.0502(6) Uani 1 1 d . . . . .
H21 H 0.0561 0.4175 0.4716 0.060 Uiso 1 1 calc R U . . .
C22 C 0.0374(3) 0.2617(2) 0.37054(16) 0.0442(5) Uani 1 1 d . . . . .
H22 H -0.0683 0.2196 0.3654 0.053 Uiso 1 1 calc R U . . .
C23 C 0.1182(2) 0.20405(18) 0.31455(14) 0.0327(5) Uani 1 1 d . . . . .
C24 C 0.0340(2) 0.07098(18) 0.24745(14) 0.0352(5) Uani 1 1 d . . . . .
H24 H -0.0509 0.0679 0.2065 0.042 Uiso 1 1 calc R U . . .
C25 C 0.1332(2) 0.02070(19) 0.18645(15) 0.0375(5) Uani 1 1 d . . . . .
H25 H 0.0747 -0.0315 0.1236 0.045 Uiso 1 1 calc R U . . .
C26 C 0.3641(2) 0.08310(18) 0.10599(14) 0.0359(5) Uani 1 1 d . . . . .
H26 H 0.3506 -0.0040 0.1001 0.043 Uiso 1 1 calc R U . . .
C27 C 0.3091(3) 0.0907(2) 0.01318(16) 0.0444(6) Uani 1 1 d . . . . .
C28 C -0.2811(3) -0.0311(3) 0.3250(2) 0.0638(7) Uani 1 1 d . . . . .
H28 H -0.2776 0.0052 0.2753 0.077 Uiso 1 1 calc R U . . .
C29 C -0.4090(3) -0.0609(3) 0.3710(3) 0.0876(10) Uani 1 1 d . . . . .
H29 H -0.4911 -0.0448 0.3523 0.105 Uiso 1 1 calc R U . . .
C30 C -0.4141(4) -0.1145(4) 0.4443(2) 0.0912(11) Uani 1 1 d . . . . .
H30 H -0.5000 -0.1347 0.4754 0.109 Uiso 1 1 calc R U . . .
C31 C -0.2932(4) -0.1385(3) 0.4720(2) 0.0788(9) Uani 1 1 d . . . . .
H31 H -0.2976 -0.1751 0.5216 0.095 Uiso 1 1 calc R U . . .
C32 C -0.1664(3) -0.1089(2) 0.42692(16) 0.0559(6) Uani 1 1 d . . . . .
H32 H -0.0848 -0.1252 0.4462 0.067 Uiso 1 1 calc R U . . .
C33 C -0.1585(3) -0.0544(2) 0.35213(16) 0.0438(5) Uani 1 1 d . . . . .
C34 C -0.0261(2) -0.02945(19) 0.29969(15) 0.0388(5) Uani 1 1 d . . . . .
C35 C 0.1619(5) 0.6813(5) 0.3654(5) 0.162(3) Uani 1 1 d . . . . .
H35A H 0.2384 0.7676 0.3792 0.194 Uiso 1 1 calc R U . . .
H35B H 0.1735 0.6493 0.4186 0.194 Uiso 1 1 calc R U . . .
C36 C 0.1873(10) 0.6087(10) 0.2842(5) 0.286(6) Uani 1 1 d . . . . .
H36A H 0.0999 0.5291 0.2618 0.429 Uiso 1 1 calc R U . . .
H36B H 0.2760 0.5941 0.2984 0.429 Uiso 1 1 calc R U . . .
H36C H 0.2037 0.6522 0.2358 0.429 Uiso 1 1 calc R U . . .
N1 N 0.72415(19) 0.47230(17) 0.29890(12) 0.0420(4) Uani 1 1 d . . . . .
H1 H 0.8105 0.5266 0.3318 0.050 Uiso 1 1 calc R U . . .
N2 N 0.26972(18) 0.11726(15) 0.17546(11) 0.0342(4) Uani 1 1 d . . . . .
N3 N 0.2574(3) 0.0934(2) -0.05725(16) 0.0696(7) Uani 1 1 d . . . . .
N4 N 0.0502(2) -0.09738(17) 0.29406(14) 0.0472(5) Uani 1 1 d . . . . .
O1 O 0.69990(18) 0.30175(16) 0.35362(11) 0.0517(4) Uani 1 1 d . . . . .
O2 O 0.16728(17) -0.05952(14) 0.23777(12) 0.0503(4) Uani 1 1 d . . . . .
O3 O 0.0181(2) 0.68101(19) 0.35661(18) 0.0802(6) Uani 1 1 d . . . . .
H3A H 0.0225 0.7416 0.3383 0.120 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C6 1.389(3) . ?
C1 N1 1.404(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(3) . ?
C7 C17 1.537(2) . ?
C7 C8 1.540(3) . ?
C7 C9 1.564(3) . ?
C8 O1 1.221(2) . ?
C8 N1 1.352(3) . ?
C9 C10 1.512(3) . ?
C9 C26 1.552(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.380(3) . ?
C10 C16 1.381(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.379(3) . ?
C13 C14 1.508(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N2 1.468(2) . ?
C17 C18 1.503(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.391(3) . ?
C18 C23 1.400(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.524(3) . ?
C24 C25 1.516(3) . ?
C24 C34 1.516(3) . ?
C24 H24 0.9800 . ?
C25 N2 1.413(2) . ?
C25 O2 1.477(2) . ?
C25 H25 0.9800 . ?
C26 N2 1.469(2) . ?
C26 C27 1.478(3) . ?
C26 H26 0.9800 . ?
C27 N3 1.143(3) . ?
C28 C33 1.380(3) . ?
C28 C29 1.382(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.371(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.366(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.395(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.471(3) . ?
C34 N4 1.281(3) . ?
C35 C36 1.377(8) . ?
C35 O3 1.381(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N1 H1 0.8600 . ?
N4 O2 1.409(2) . ?
O3 H3A 0.8200 . ?

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
C2 C1 C6 122.4(2) . . ?
C2 C1 N1 127.86(19) . . ?
C6 C1 N1 109.75(17) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.33(18) . . ?
C5 C6 C7 132.58(17) . . ?
C1 C6 C7 108.10(16) . . ?
C6 C7 C17 117.48(15) . . ?
C6 C7 C8 102.60(15) . . ?
C17 C7 C8 114.42(15) . . ?
C6 C7 C9 115.94(15) . . ?
C17 C7 C9 99.22(14) . . ?
C8 C7 C9 107.30(15) . . ?
O1 C8 N1 127.06(19) . . ?
O1 C8 C7 125.46(19) . . ?
N1 C8 C7 107.46(17) . . ?
C10 C9 C26 120.97(16) . . ?
C10 C9 C7 116.13(15) . . ?
C26 C9 C7 104.04(15) . . ?
C10 C9 H9 104.7 . . ?
C26 C9 H9 104.7 . . ?
C7 C9 H9 104.7 . . ?
C11 C10 C16 117.09(19) . . ?
C11 C10 C9 117.79(18) . . ?
C16 C10 C9 125.08(18) . . ?
C10 C11 C12 121.6(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C15 117.0(2) . . ?
C12 C13 C14 122.0(2) . . ?
C15 C13 C14 121.1(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.9(2) . . ?
C13 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C10 C16 C15 121.0(2) . . ?
C10 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N2 C17 C18 109.29(15) . . ?
N2 C17 C7 101.76(14) . . ?
C18 C17 C7 119.80(16) . . ?
N2 C17 H17 108.5 . . ?
C18 C17 H17 108.5 . . ?
C7 C17 H17 108.5 . . ?
C19 C18 C23 119.24(18) . . ?
C19 C18 C17 121.48(17) . . ?
C23 C18 C17 119.22(17) . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 118.91(19) . . ?
C22 C23 C24 119.90(18) . . ?
C18 C23 C24 121.18(17) . . ?
C25 C24 C34 99.57(16) . . ?
C25 C24 C23 115.01(16) . . ?
C34 C24 C23 112.95(16) . . ?
C25 C24 H24 109.6 . . ?
C34 C24 H24 109.6 . . ?
C23 C24 H24 109.6 . . ?
N2 C25 O2 110.69(16) . . ?
N2 C25 C24 113.18(17) . . ?
O2 C25 C24 104.04(15) . . ?
N2 C25 H25 109.6 . . ?
O2 C25 H25 109.6 . . ?
C24 C25 H25 109.6 . . ?
N2 C26 C27 107.49(17) . . ?
N2 C26 C9 103.53(15) . . ?
C27 C26 C9 117.91(16) . . ?
N2 C26 H26 109.2 . . ?
C27 C26 H26 109.2 . . ?
C9 C26 H26 109.2 . . ?
N3 C27 C26 175.7(2) . . ?
C33 C28 C29 120.8(3) . . ?
C33 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 119.6(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.4(3) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 118.6(2) . . ?
C28 C33 C34 120.8(2) . . ?
C32 C33 C34 120.5(2) . . ?
N4 C34 C33 119.97(19) . . ?
N4 C34 C24 113.19(18) . . ?
C33 C34 C24 126.84(19) . . ?
C36 C35 O3 112.5(6) . . ?
C36 C35 H35A 109.1 . . ?
O3 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
O3 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C8 N1 C1 111.83(17) . . ?
C8 N1 H1 124.1 . . ?
C1 N1 H1 124.1 . . ?
C25 N2 C17 115.22(15) . . ?
C25 N2 C26 118.64(16) . . ?
C17 N2 C26 110.50(15) . . ?
C34 N4 O2 109.89(16) . . ?
N4 O2 C25 107.25(14) . . ?
C35 O3 H3A 109.5 . . ?

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
N1 H1 O3 0.86 2.06 2.864(2) 154.6 1_655
O3 H3A N4 0.82 2.10 2.923(3) 176.1 1_565

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_ZY181025
_database_code_depnum_ccdc_archive 'CCDC 1937500'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H30 Cl N3 O4'
_chemical_formula_sum            'C36 H30 Cl N3 O4'
_chemical_formula_weight         604.08

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                   15.4886(12)
_cell_length_b                   8.8793(6)
_cell_length_c                   22.4459(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.902(3)
_cell_angle_gamma                90
_cell_volume                     3020.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9552
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             1264
_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    0.172
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.966
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31963
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5919
_reflns_number_gt                3810
_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)+(0.0628P)²+1.2599P] 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         5919
_refine_ls_number_parameters     409
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.070
_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 0.44082(14) 0.4802(3) 0.12190(11) 0.0475(6) Uani 1 1 d . . . . .
C2 C 0.43310(13) 0.6496(2) 0.13413(9) 0.0406(5) Uani 1 1 d . . . . .
C3 C 0.46748(13) 0.6596(2) 0.20192(10) 0.0399(5) Uani 1 1 d . . . . .
C4 C 0.47092(15) 0.7772(3) 0.24246(10) 0.0494(6) Uani 1 1 d . . . . .
H4 H 0.4475 0.8709 0.2295 0.059 Uiso 1 1 calc R U . . .
C5 C 0.51001(18) 0.7527(3) 0.30291(11) 0.0602(7) Uani 1 1 d . . . . .
H5 H 0.5123 0.8308 0.3308 0.072 Uiso 1 1 calc R U . . .
C6 C 0.54542(17) 0.6150(3) 0.32229(12) 0.0630(7) Uani 1 1 d . . . . .
H6 H 0.5728 0.6023 0.3629 0.076 Uiso 1 1 calc R U . . .
C7 C 0.54108(15) 0.4956(3) 0.28272(12) 0.0574(6) Uani 1 1 d . . . . .
H7 H 0.5649 0.4023 0.2958 0.069 Uiso 1 1 calc R U . . .
C8 C 0.50017(13) 0.5197(2) 0.22297(10) 0.0438(5) Uani 1 1 d . . . . .
C9 C 0.48967(14) 0.7343(2) 0.09398(10) 0.0439(5) Uani 1 1 d . . . . .
H9 H 0.4750 0.6858 0.0540 0.053 Uiso 1 1 calc R U . . .
C10 C 0.58797(14) 0.7143(2) 0.11503(10) 0.0465(5) Uani 1 1 d . U . . .
C11 C 0.63654(15) 0.7761(3) 0.16807(11) 0.0535(6) Uani 1 1 d . U . . .
H11 H 0.6092 0.8420 0.1905 0.064 Uiso 1 1 calc R U . . .
C12 C 0.72443(17) 0.7422(3) 0.18834(13) 0.0664(7) Uani 1 1 d . U . . .
H12 H 0.7561 0.7860 0.2238 0.080 Uiso 1 1 calc R U . . .
C13 C 0.76467(17) 0.6442(3) 0.15606(16) 0.0727(8) Uani 1 1 d . U . . .
C14 C 0.71987(19) 0.5831(3) 0.10346(16) 0.0812(9) Uani 1 1 d . U . . .
H14 H 0.7481 0.5172 0.0815 0.097 Uiso 1 1 calc R U . . .
C15 C 0.63145(18) 0.6191(3) 0.08224(13) 0.0653(7) Uani 1 1 d . U . . .
H15 H 0.6012 0.5786 0.0456 0.078 Uiso 1 1 calc R U . . .
C16 C 0.34227(13) 0.7184(2) 0.10959(10) 0.0427(5) Uani 1 1 d . . . . .
H16 H 0.3193 0.6810 0.0683 0.051 Uiso 1 1 calc R U . . .
C17 C 0.27260(13) 0.7015(2) 0.14706(10) 0.0446(5) Uani 1 1 d . . . . .
C18 C 0.26931(15) 0.5825(3) 0.18665(11) 0.0574(6) Uani 1 1 d . . . . .
H18 H 0.3102 0.5049 0.1894 0.069 Uiso 1 1 calc R U . . .
C19 C 0.20609(17) 0.5778(4) 0.22201(13) 0.0726(8) Uani 1 1 d . . . . .
H19 H 0.2040 0.4964 0.2478 0.087 Uiso 1 1 calc R U . . .
C20 C 0.14638(18) 0.6931(4) 0.21905(13) 0.0764(9) Uani 1 1 d . . . . .
H20 H 0.1050 0.6918 0.2438 0.092 Uiso 1 1 calc R U . . .
C21 C 0.14788(16) 0.8111(3) 0.17927(12) 0.0635(7) Uani 1 1 d . . . . .
H21 H 0.1073 0.8891 0.1774 0.076 Uiso 1 1 calc R U . . .
C22 C 0.20914(14) 0.8149(3) 0.14203(10) 0.0484(6) Uani 1 1 d . . . . .
C23 C 0.20485(15) 0.9320(3) 0.09261(11) 0.0519(6) Uani 1 1 d . . . . .
H23 H 0.1748 1.0223 0.1031 0.062 Uiso 1 1 calc R U . . .
C24 C 0.29440(15) 0.9758(3) 0.07808(11) 0.0550(6) Uani 1 1 d . . . . .
H24 H 0.3084 1.0800 0.0910 0.066 Uiso 1 1 calc R U . . .
C25 C 0.44697(14) 0.8942(2) 0.08448(10) 0.0452(5) Uani 1 1 d . . . . .
H25 H 0.4311 0.9132 0.0406 0.054 Uiso 1 1 calc R U . . .
C26 C 0.50220(15) 1.0253(2) 0.11359(12) 0.0488(6) Uani 1 1 d . . . . .
C27 C 0.62005(18) 1.1875(3) 0.09718(15) 0.0779(6) Uani 1 1 d . U . . .
H27A H 0.6360 1.2281 0.0608 0.093 Uiso 1 1 calc R U . . .
H27B H 0.5891 1.2655 0.1146 0.093 Uiso 1 1 calc R U . . .
C28 C 0.6991(2) 1.1474(4) 0.14025(17) 0.1003(8) Uani 1 1 d . U . . .
H28A H 0.6841 1.1181 0.1780 0.150 Uiso 1 1 calc R U . . .
H28B H 0.7383 1.2323 0.1470 0.150 Uiso 1 1 calc R U . . .
H28C H 0.7276 1.0649 0.1244 0.150 Uiso 1 1 calc R U . . .
C29 C 0.15769(16) 0.8731(3) 0.03094(11) 0.0531(6) Uani 1 1 d . . . . .
C30 C 0.06967(16) 0.8022(3) 0.01647(10) 0.0529(6) Uani 1 1 d . U . . .
C31 C 0.00349(17) 0.8440(3) 0.04620(12) 0.0624(7) Uani 1 1 d . U . . .
H31 H 0.0158 0.9119 0.0784 0.075 Uiso 1 1 calc R U . . .
C32 C -0.08109(17) 0.7857(3) 0.02841(14) 0.0690(7) Uani 1 1 d . U . . .
H32 H -0.1245 0.8145 0.0492 0.083 Uiso 1 1 calc R U . . .
C33 C -0.10192(19) 0.6861(3) -0.01928(13) 0.0696(7) Uani 1 1 d . U . . .
C34 C -0.1947(2) 0.6259(4) -0.03972(17) 0.1023(12) Uani 1 1 d . . . . .
H34A H -0.1960 0.5214 -0.0290 0.153 Uiso 1 1 calc R U . . .
H34B H -0.2128 0.6367 -0.0831 0.153 Uiso 1 1 calc R U . . .
H34C H -0.2341 0.6815 -0.0201 0.153 Uiso 1 1 calc R U . . .
C35 C -0.0355(2) 0.6428(3) -0.04821(13) 0.0760(8) Uani 1 1 d . U . . .
H35 H -0.0479 0.5740 -0.0801 0.091 Uiso 1 1 calc R U . . .
C36 C 0.04901(19) 0.6992(3) -0.03096(11) 0.0645(7) Uani 1 1 d . U . . .
H36 H 0.0925 0.6680 -0.0513 0.077 Uiso 1 1 calc R U . . .
Cl1 Cl 0.8763(3) 0.5979(5) 0.1908(4) 0.0888(19) Uani 0.57(3) 1 d . . P A 1
Cl1' Cl 0.8697(6) 0.5860(9) 0.1686(13) 0.154(3) Uani 0.43(3) 1 d . . P A 2
N1 N 0.48315(12) 0.4161(2) 0.17461(9) 0.0517(5) Uani 1 1 d . . . . .
H1 H 0.4979 0.3227 0.1781 0.062 Uiso 1 1 calc R U . . .
N2 N 0.36450(11) 0.87926(19) 0.10694(8) 0.0445(4) Uani 1 1 d . . . . .
N3 N 0.20017(14) 0.8907(3) -0.01137(10) 0.0685(6) Uani 1 1 d . . . . .
O1 O 0.41652(12) 0.41779(19) 0.07331(8) 0.0667(5) Uani 1 1 d . . . . .
O2 O 0.49217(11) 1.09243(18) 0.15836(8) 0.0600(5) Uani 1 1 d . . . . .
O3 O 0.56176(11) 1.0593(2) 0.08067(9) 0.0716(5) Uani 1 1 d . U . . .
O4 O 0.27992(12) 0.9670(2) 0.01159(8) 0.0763(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 O1 1.212(3) . ?
C1 N1 1.354(3) . ?
C1 C2 1.538(3) . ?
C2 C3 1.508(3) . ?
C2 C16 1.529(3) . ?
C2 C9 1.573(3) . ?
C3 C4 1.379(3) . ?
C3 C8 1.386(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.406(3) . ?
C9 C10 1.509(3) . ?
C9 C25 1.562(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.384(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(4) . ?
C13 Cl1' 1.675(8) . ?
C13 Cl1 1.792(5) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.473(3) . ?
C16 C17 1.506(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.388(3) . ?
C17 C22 1.395(3) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.512(3) . ?
C23 C29 1.519(3) . ?
C23 C24 1.539(3) . ?
C23 H23 0.9800 . ?
C24 N2 1.430(3) . ?
C24 O4 1.465(3) . ?
C24 H24 0.9800 . ?
C25 N2 1.473(3) . ?
C25 C26 1.511(3) . ?
C25 H25 0.9800 . ?
C26 O2 1.206(3) . ?
C26 O3 1.330(3) . ?
C27 C28 1.440(4) . ?
C27 O3 1.453(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.272(3) . ?
C29 C30 1.476(3) . ?
C30 C31 1.384(3) . ?
C30 C36 1.390(4) . ?
C31 C32 1.389(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(4) . ?
C32 H32 0.9300 . ?
C33 C35 1.380(4) . ?
C33 C34 1.512(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.380(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N1 H1 0.8600 . ?
N3 O4 1.410(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 126.8(2) . . ?
O1 C1 C2 125.9(2) . . ?
N1 C1 C2 107.24(18) . . ?
C3 C2 C16 116.58(17) . . ?
C3 C2 C1 102.33(17) . . ?
C16 C2 C1 115.25(17) . . ?
C3 C2 C9 115.32(17) . . ?
C16 C2 C9 100.50(17) . . ?
C1 C2 C9 107.02(17) . . ?
C4 C3 C8 119.5(2) . . ?
C4 C3 C2 131.9(2) . . ?
C8 C3 C2 108.63(18) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C7 C8 C3 122.2(2) . . ?
C7 C8 N1 128.7(2) . . ?
C3 C8 N1 109.02(19) . . ?
C10 C9 C25 121.43(18) . . ?
C10 C9 C2 114.19(18) . . ?
C25 C9 C2 104.06(16) . . ?
C10 C9 H9 105.3 . . ?
C25 C9 H9 105.3 . . ?
C2 C9 H9 105.3 . . ?
C15 C10 C11 117.5(2) . . ?
C15 C10 C9 118.4(2) . . ?
C11 C10 C9 123.9(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 Cl1' 109.2(10) . . ?
C12 C13 Cl1' 130.0(9) . . ?
C14 C13 Cl1 124.3(4) . . ?
C12 C13 Cl1 114.9(4) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.7(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N2 C16 C17 108.62(17) . . ?
N2 C16 C2 101.36(16) . . ?
C17 C16 C2 118.11(18) . . ?
N2 C16 H16 109.4 . . ?
C17 C16 H16 109.4 . . ?
C2 C16 H16 109.4 . . ?
C18 C17 C22 118.9(2) . . ?
C18 C17 C16 123.9(2) . . ?
C22 C17 C16 117.2(2) . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 C23 121.8(2) . . ?
C17 C22 C23 118.6(2) . . ?
C22 C23 C29 111.8(2) . . ?
C22 C23 C24 115.10(18) . . ?
C29 C23 C24 100.32(19) . . ?
C22 C23 H23 109.7 . . ?
C29 C23 H23 109.7 . . ?
C24 C23 H23 109.7 . . ?
N2 C24 O4 111.84(19) . . ?
N2 C24 C23 112.69(19) . . ?
O4 C24 C23 104.31(19) . . ?
N2 C24 H24 109.3 . . ?
O4 C24 H24 109.3 . . ?
C23 C24 H24 109.3 . . ?
N2 C25 C26 112.03(19) . . ?
N2 C25 C9 104.13(16) . . ?
C26 C25 C9 117.06(18) . . ?
N2 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C9 C25 H25 107.7 . . ?
O2 C26 O3 125.0(2) . . ?
O2 C26 C25 125.6(2) . . ?
O3 C26 C25 109.3(2) . . ?
C28 C27 O3 112.0(3) . . ?
C28 C27 H27A 109.2 . . ?
O3 C27 H27A 109.2 . . ?
C28 C27 H27B 109.2 . . ?
O3 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C30 119.0(2) . . ?
N3 C29 C23 114.4(2) . . ?
C30 C29 C23 126.6(2) . . ?
C31 C30 C36 118.0(2) . . ?
C31 C30 C29 121.5(2) . . ?
C36 C30 C29 120.4(2) . . ?
C30 C31 C32 120.6(3) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 121.3(3) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C32 C33 C35 117.9(3) . . ?
C32 C33 C34 121.3(3) . . ?
C35 C33 C34 120.9(3) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 C36 121.5(3) . . ?
C33 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C35 C36 C30 120.6(3) . . ?
C35 C36 H36 119.7 . . ?
C30 C36 H36 119.7 . . ?
C1 N1 C8 112.30(18) . . ?
C1 N1 H1 123.8 . . ?
C8 N1 H1 123.8 . . ?
C24 N2 C25 114.97(18) . . ?
C24 N2 C16 115.97(18) . . ?
C25 N2 C16 109.12(16) . . ?
C29 N3 O4 109.6(2) . . ?
C26 O3 C27 120.1(2) . . ?
N3 O4 C24 109.67(18) . . ?

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
N1 H1 O2 0.86 2.09 2.904(2) 157.7 1_545

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_ZY171122
_database_code_depnum_ccdc_archive 'CCDC 1937602'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-08-08 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 H27 N3 O3'
_chemical_formula_sum            'C36 H27 N3 O3'
_chemical_formula_weight         549.60

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      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                   9.5390(12)
_cell_length_b                   20.876(3)
_cell_length_c                   14.712(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.212(5)
_cell_angle_gamma                90
_cell_volume                     2783.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6228
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1152
_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    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.983
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23283
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5374
_reflns_number_gt                3328
_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)+(0.0496P)²+2.2482P] 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         5374
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.2231(3) 0.94731(13) 0.6161(2) 0.0320(7) Uani 1 1 d . . . . .
C2 C 0.3440(3) 0.90029(12) 0.6404(2) 0.0331(7) Uani 1 1 d . . . . .
C3 C 0.4403(3) 0.88507(15) 0.5903(2) 0.0441(8) Uani 1 1 d . . . . .
H3 H 0.4361 0.9061 0.5338 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5426(4) 0.83756(17) 0.6270(3) 0.0580(10) Uani 1 1 d . . . . .
H4 H 0.6080 0.8258 0.5945 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5493(4) 0.80722(18) 0.7114(3) 0.0678(11) Uani 1 1 d . . . . .
H5 H 0.6184 0.7748 0.7340 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4564(4) 0.82335(16) 0.7637(3) 0.0552(9) Uani 1 1 d . . . . .
H6 H 0.4638 0.8034 0.8215 0.066 Uiso 1 1 calc R U . . .
C7 C 0.3520(3) 0.87042(13) 0.7261(2) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.2363(3) 0.89640(13) 0.7640(2) 0.0344(7) Uani 1 1 d . . . . .
C9 C 0.1495(3) 0.94688(12) 0.69369(19) 0.0299(6) Uani 1 1 d . . . . .
C10 C -0.0195(3) 0.93565(12) 0.6494(2) 0.0321(6) Uani 1 1 d . . . . .
H10 H -0.0530 0.9653 0.5952 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0732(3) 0.86976(12) 0.6101(2) 0.0327(7) Uani 1 1 d . . . . .
C12 C -0.1443(3) 0.86417(13) 0.5127(2) 0.0390(7) Uani 1 1 d . . . . .
H12 H -0.1560 0.9006 0.4747 0.047 Uiso 1 1 calc R U . . .
C13 C -0.1989(3) 0.80602(14) 0.4696(2) 0.0456(8) Uani 1 1 d . . . . .
C14 C -0.2755(5) 0.80226(18) 0.3635(3) 0.0751(12) Uani 1 1 d . . . . .
H14A H -0.3015 0.7586 0.3456 0.113 Uiso 1 1 calc R U . . .
H14B H -0.2107 0.8178 0.3299 0.113 Uiso 1 1 calc R U . . .
H14C H -0.3633 0.8280 0.3472 0.113 Uiso 1 1 calc R U . . .
C15 C -0.1802(3) 0.75246(14) 0.5267(3) 0.0514(9) Uani 1 1 d . . . . .
H15 H -0.2157 0.7131 0.4996 0.062 Uiso 1 1 calc R U . . .
C16 C -0.1095(4) 0.75658(14) 0.6236(3) 0.0511(9) Uani 1 1 d . . . . .
H16 H -0.0968 0.7199 0.6613 0.061 Uiso 1 1 calc R U . . .
C17 C -0.0571(3) 0.81484(14) 0.6656(2) 0.0442(8) Uani 1 1 d . . . . .
H17 H -0.0109 0.8172 0.7313 0.053 Uiso 1 1 calc R U . . .
C18 C 0.0468(3) 1.00739(14) 0.8817(2) 0.0351(7) Uani 1 1 d . . . . .
H18 H 0.0632 0.9631 0.9047 0.042 Uiso 1 1 calc R U . . .
C19 C 0.1701(3) 1.05012(12) 0.93942(19) 0.0335(7) Uani 1 1 d . . . . .
H19 H 0.2052 1.0326 1.0044 0.040 Uiso 1 1 calc R U . . .
C20 C 0.3017(3) 1.05457(12) 0.9033(2) 0.0314(6) Uani 1 1 d . . . . .
C21 C 0.4385(3) 1.07467(12) 0.9656(2) 0.0375(7) Uani 1 1 d . . . . .
H21 H 0.4470 1.0850 1.0286 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5603(3) 1.07926(13) 0.9346(2) 0.0414(8) Uani 1 1 d . . . . .
H22 H 0.6503 1.0928 0.9764 0.050 Uiso 1 1 calc R U . . .
C23 C 0.5483(3) 1.06388(14) 0.8420(2) 0.0448(8) Uani 1 1 d . . . . .
H23 H 0.6299 1.0676 0.8205 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4147(3) 1.04274(13) 0.7804(2) 0.0394(7) Uani 1 1 d . . . . .
H24 H 0.4077 1.0320 0.7177 0.047 Uiso 1 1 calc R U . . .
C25 C 0.2903(3) 1.03722(12) 0.81081(19) 0.0297(6) Uani 1 1 d . . . . .
C26 C 0.1467(3) 1.01380(12) 0.74081(19) 0.0292(6) Uani 1 1 d . . . . .
H26 H 0.1184 1.0451 0.6886 0.035 Uiso 1 1 calc R U . . .
C27 C -0.0817(3) 0.96142(13) 0.7265(2) 0.0357(7) Uani 1 1 d . . . . .
H27 H -0.0849 0.9263 0.7701 0.043 Uiso 1 1 calc R U . . .
C28 C -0.2308(3) 0.98729(14) 0.6854(2) 0.0440(8) Uani 1 1 d . . . . .
C29 C 0.2493(3) 1.20517(14) 0.9568(2) 0.0446(8) Uani 1 1 d . . . . .
H29 H 0.2807 1.1888 0.9077 0.054 Uiso 1 1 calc R U . . .
C30 C 0.3106(4) 1.26115(15) 1.0019(3) 0.0521(9) Uani 1 1 d . . . . .
H30 H 0.3828 1.2819 0.9825 0.062 Uiso 1 1 calc R U . . .
C31 C 0.2671(4) 1.28702(14) 1.0753(2) 0.0522(9) Uani 1 1 d . . . . .
C32 C 0.3410(5) 1.34633(16) 1.1289(3) 0.0817(13) Uani 1 1 d . . . . .
H32A H 0.4309 1.3343 1.1771 0.122 Uiso 1 1 calc R U . . .
H32B H 0.2760 1.3665 1.1586 0.122 Uiso 1 1 calc R U . . .
H32C H 0.3628 1.3757 1.0849 0.122 Uiso 1 1 calc R U . . .
C33 C 0.1554(4) 1.25623(16) 1.0996(2) 0.0551(9) Uani 1 1 d . . . . .
H33 H 0.1210 1.2738 1.1467 0.066 Uiso 1 1 calc R U . . .
C34 C 0.0937(4) 1.19987(15) 1.0553(2) 0.0480(8) Uani 1 1 d . . . . .
H34 H 0.0196 1.1798 1.0736 0.058 Uiso 1 1 calc R U . . .
C35 C 0.1413(3) 1.17299(13) 0.9840(2) 0.0384(7) Uani 1 1 d . . . . .
C36 C 0.0810(3) 1.11027(14) 0.9430(2) 0.0362(7) Uani 1 1 d . . . . .
N1 N 0.0233(2) 1.01009(10) 0.78024(16) 0.0321(5) Uani 1 1 d . . . . .
N2 N -0.3462(3) 1.00845(15) 0.6518(2) 0.0690(9) Uani 1 1 d . . . . .
N3 N -0.0575(3) 1.09958(12) 0.92195(18) 0.0471(7) Uani 1 1 d . . . . .
O1 O 0.1853(2) 0.98072(10) 0.54529(15) 0.0482(6) Uani 1 1 d . . . . .
O2 O 0.2147(2) 0.88120(10) 0.83815(15) 0.0482(6) Uani 1 1 d . . . . .
O3 O -0.0837(2) 1.03315(10) 0.89741(15) 0.0485(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 O1 1.211(3) . ?
C1 C2 1.471(4) . ?
C1 C9 1.516(4) . ?
C2 C3 1.382(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(4) . ?
C8 O2 1.214(3) . ?
C8 C9 1.527(4) . ?
C9 C10 1.556(4) . ?
C9 C26 1.563(4) . ?
C10 C11 1.518(4) . ?
C10 C27 1.533(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.385(4) . ?
C11 C17 1.388(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9300 . ?
C13 C15 1.377(4) . ?
C13 C14 1.505(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.440(3) . ?
C18 O3 1.440(3) . ?
C18 C19 1.509(4) . ?
C18 H18 0.9800 . ?
C19 C20 1.511(4) . ?
C19 C36 1.526(4) . ?
C19 H19 0.9800 . ?
C20 C25 1.380(4) . ?
C20 C21 1.404(4) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.515(4) . ?
C26 N1 1.468(3) . ?
C26 H26 0.9800 . ?
C27 C28 1.464(4) . ?
C27 N1 1.471(3) . ?
C27 H27 0.9800 . ?
C28 N2 1.145(4) . ?
C29 C30 1.380(4) . ?
C29 C35 1.389(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(5) . ?
C30 H30 0.9300 . ?
C31 C33 1.384(5) . ?
C31 C32 1.518(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.384(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.386(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.481(4) . ?
C36 N3 1.279(3) . ?
N3 O3 1.435(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.4(3) . . ?
O1 C1 C9 124.6(2) . . ?
C2 C1 C9 109.0(2) . . ?
C3 C2 C7 121.7(3) . . ?
C3 C2 C1 128.6(3) . . ?
C7 C2 C1 109.7(2) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 C8 129.5(3) . . ?
C2 C7 C8 109.9(2) . . ?
O2 C8 C7 126.6(3) . . ?
O2 C8 C9 125.5(3) . . ?
C7 C8 C9 107.9(2) . . ?
C1 C9 C8 103.5(2) . . ?
C1 C9 C10 110.4(2) . . ?
C8 C9 C10 116.8(2) . . ?
C1 C9 C26 113.9(2) . . ?
C8 C9 C26 113.4(2) . . ?
C10 C9 C26 99.3(2) . . ?
C11 C10 C27 115.9(2) . . ?
C11 C10 C9 118.6(2) . . ?
C27 C10 C9 103.1(2) . . ?
C11 C10 H10 106.1 . . ?
C27 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
C12 C11 C17 117.9(3) . . ?
C12 C11 C10 117.9(2) . . ?
C17 C11 C10 124.3(3) . . ?
C11 C12 C13 122.5(3) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C15 C13 C12 118.1(3) . . ?
C15 C13 C14 121.3(3) . . ?
C12 C13 C14 120.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C13 C15 H15 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C11 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C11 C17 H17 119.8 . . ?
N1 C18 O3 106.9(2) . . ?
N1 C18 C19 113.7(2) . . ?
O3 C18 C19 104.5(2) . . ?
N1 C18 H18 110.5 . . ?
O3 C18 H18 110.5 . . ?
C19 C18 H18 110.5 . . ?
C18 C19 C20 115.2(2) . . ?
C18 C19 C36 99.3(2) . . ?
C20 C19 C36 119.6(2) . . ?
C18 C19 H19 107.3 . . ?
C20 C19 H19 107.3 . . ?
C36 C19 H19 107.3 . . ?
C25 C20 C21 119.5(3) . . ?
C25 C20 C19 120.8(2) . . ?
C21 C20 C19 119.6(3) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 121.1(3) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C24 118.8(2) . . ?
C20 C25 C26 122.1(2) . . ?
C24 C25 C26 119.1(2) . . ?
N1 C26 C25 114.5(2) . . ?
N1 C26 C9 104.76(19) . . ?
C25 C26 C9 116.9(2) . . ?
N1 C26 H26 106.7 . . ?
C25 C26 H26 106.7 . . ?
C9 C26 H26 106.7 . . ?
C28 C27 N1 112.2(2) . . ?
C28 C27 C10 111.9(2) . . ?
N1 C27 C10 106.5(2) . . ?
C28 C27 H27 108.7 . . ?
N1 C27 H27 108.7 . . ?
C10 C27 H27 108.7 . . ?
N2 C28 C27 178.4(4) . . ?
C30 C29 C35 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C35 C29 H29 119.6 . . ?
C29 C30 C31 121.4(3) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C33 117.7(3) . . ?
C30 C31 C32 121.4(3) . . ?
C33 C31 C32 120.9(3) . . ?
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 . . ?
C31 C33 C34 121.4(3) . . ?
C31 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C35 120.6(3) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C29 118.0(3) . . ?
C34 C35 C36 119.3(3) . . ?
C29 C35 C36 122.6(3) . . ?
N3 C36 C35 119.6(3) . . ?
N3 C36 C19 113.1(3) . . ?
C35 C36 C19 126.3(2) . . ?
C18 N1 C26 121.9(2) . . ?
C18 N1 C27 112.9(2) . . ?
C26 N1 C27 108.6(2) . . ?
C36 N3 O3 108.4(2) . . ?
N3 O3 C18 108.05(19) . . ?

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047




#==================================================================================
####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 1937506'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 F N5 O3, C H2 Cl2'
_chemical_formula_sum            'C37 H30 Cl2 F N5 O3'
_chemical_formula_weight         682.56

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'
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           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                   33.399(3)
_cell_length_b                   7.9839(7)
_cell_length_c                   26.148(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.495(3)
_cell_angle_gamma                90
_cell_volume                     6531.1(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             2832
_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    0.251
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33725
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6396
_reflns_number_gt                4408
_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)+(0.0840P)²+11.0254P] 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         6396
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.23192(8) 0.4491(3) 0.34985(9) 0.0316(6) Uani 1 1 d . . . . .
H1 H 0.2468 0.3580 0.3388 0.038 Uiso 1 1 calc R U . . .
C2 C 0.25668(8) 0.5007(3) 0.40815(9) 0.0299(5) Uani 1 1 d . . . . .
C3 C 0.24781(8) 0.4380(3) 0.45282(9) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.2280 0.3521 0.4477 0.040 Uiso 1 1 calc R U . . .
C4 C 0.26800(9) 0.5014(4) 0.50447(10) 0.0400(6) Uani 1 1 d . . . . .
H4 H 0.2620 0.4573 0.5339 0.048 Uiso 1 1 calc R U . . .
C5 C 0.29709(9) 0.6297(4) 0.51269(11) 0.0430(7) Uani 1 1 d . . . . .
H5 H 0.3100 0.6753 0.5473 0.052 Uiso 1 1 calc R U . . .
C6 C 0.30691(9) 0.6903(4) 0.46905(11) 0.0417(7) Uani 1 1 d . . . . .
H6 H 0.3264 0.7775 0.4746 0.050 Uiso 1 1 calc R U . . .
C7 C 0.28803(8) 0.6229(3) 0.41671(10) 0.0347(6) Uani 1 1 d . . . . .
C8 C 0.30090(9) 0.6810(3) 0.36978(10) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.3143 0.7916 0.3786 0.047 Uiso 1 1 calc R U . . .
C9 C 0.26326(9) 0.6929(4) 0.31534(11) 0.0419(7) Uani 1 1 d . . . . .
H9 H 0.2542 0.8101 0.3085 0.050 Uiso 1 1 calc R U . . .
C10 C 0.18886(8) 0.5972(3) 0.26837(9) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.1716 0.6935 0.2714 0.041 Uiso 1 1 calc R U . . .
C11 C 0.19360(9) 0.5993(3) 0.21377(10) 0.0394(6) Uani 1 1 d . . . . .
C12 C 0.09786(9) 0.5549(4) 0.42899(12) 0.0439(7) Uani 1 1 d . . . . .
H12 H 0.0859 0.6084 0.3955 0.053 Uiso 1 1 calc R U . . .
C13 C 0.08431(10) 0.5943(4) 0.47194(14) 0.0528(8) Uani 1 1 d . . . . .
H13 H 0.0629 0.6736 0.4671 0.063 Uiso 1 1 calc R U . . .
C14 C 0.10225(11) 0.5172(4) 0.52147(13) 0.0536(8) Uani 1 1 d . . . . .
H14 H 0.0933 0.5459 0.5503 0.064 Uiso 1 1 calc R U . . .
C15 C 0.13329(11) 0.3979(4) 0.52887(12) 0.0505(8) Uani 1 1 d . . . . .
H15 H 0.1452 0.3451 0.5625 0.061 Uiso 1 1 calc R U . . .
C16 C 0.14704(9) 0.3558(3) 0.48614(11) 0.0413(6) Uani 1 1 d . . . . .
H16 H 0.1680 0.2747 0.4909 0.050 Uiso 1 1 calc R U . . .
C17 C 0.12921(8) 0.4359(3) 0.43646(10) 0.0337(6) Uani 1 1 d . . . . .
C18 C 0.16198(8) 0.5098(3) 0.36698(9) 0.0294(5) Uani 1 1 d . . . . .
C19 C 0.18428(8) 0.4018(3) 0.33691(9) 0.0296(5) Uani 1 1 d . . . . .
C20 C 0.17631(8) 0.2291(3) 0.35396(9) 0.0313(6) Uani 1 1 d . . . . .
C21 C 0.19151(10) 0.0697(3) 0.33766(11) 0.0446(7) Uani 1 1 d . . . . .
H21A H 0.1830 -0.0226 0.3551 0.067 Uiso 1 1 calc R U . . .
H21B H 0.2221 0.0720 0.3486 0.067 Uiso 1 1 calc R U . . .
H21C H 0.1792 0.0568 0.2988 0.067 Uiso 1 1 calc R U . . .
C22 C 0.16585(8) 0.4332(3) 0.27401(9) 0.0323(6) Uani 1 1 d . . . . .
H22 H 0.1773 0.3443 0.2572 0.039 Uiso 1 1 calc R U . . .
C23 C 0.11809(8) 0.4314(4) 0.24579(10) 0.0379(6) Uani 1 1 d . . . . .
C24 C 0.09939(11) 0.2973(5) 0.21306(13) 0.0609(9) Uani 1 1 d . . . . .
H24 H 0.1165 0.2095 0.2093 0.073 Uiso 1 1 calc R U . . .
C25 C 0.05571(13) 0.2906(6) 0.18558(17) 0.0863(13) Uani 1 1 d . . . . .
H25 H 0.0434 0.1993 0.1636 0.104 Uiso 1 1 calc R U . . .
C26 C 0.03139(11) 0.4185(6) 0.19126(16) 0.0765(12) Uani 1 1 d . . . . .
C27 C 0.04804(11) 0.5548(5) 0.22252(14) 0.0685(10) Uani 1 1 d . . . . .
H27 H 0.0305 0.6419 0.2255 0.082 Uiso 1 1 calc R U . . .
C28 C 0.09187(10) 0.5609(4) 0.24985(12) 0.0536(8) Uani 1 1 d . . . . .
H28 H 0.1038 0.6537 0.2713 0.064 Uiso 1 1 calc R U . . .
C29 C 0.33063(9) 0.5660(4) 0.35277(11) 0.0416(7) Uani 1 1 d . . . . .
C30 C 0.37079(9) 0.4874(4) 0.38701(11) 0.0418(7) Uani 1 1 d . . . . .
C31 C 0.38985(10) 0.5197(4) 0.44246(12) 0.0475(7) Uani 1 1 d . . . . .
H31 H 0.3770 0.5958 0.4589 0.057 Uiso 1 1 calc R U . . .
C32 C 0.42749(10) 0.4418(4) 0.47409(13) 0.0521(8) Uani 1 1 d . . . . .
H32 H 0.4396 0.4657 0.5112 0.063 Uiso 1 1 calc R U . . .
C33 C 0.44687(9) 0.3289(4) 0.45039(13) 0.0501(7) Uani 1 1 d . . . . .
C34 C 0.49715(12) 0.2392(5) 0.53579(15) 0.0723(10) Uani 1 1 d . . . . .
H34A H 0.5083 0.3477 0.5493 0.108 Uiso 1 1 calc R U . . .
H34B H 0.5192 0.1566 0.5498 0.108 Uiso 1 1 calc R U . . .
H34C H 0.4736 0.2130 0.5475 0.108 Uiso 1 1 calc R U . . .
C35 C 0.42916(11) 0.2986(4) 0.39473(13) 0.0571(8) Uani 1 1 d . . . . .
H35 H 0.4426 0.2252 0.3783 0.069 Uiso 1 1 calc R U . . .
C36 C 0.39222(10) 0.3755(4) 0.36402(13) 0.0522(8) Uani 1 1 d . . . . .
H36 H 0.3808 0.3534 0.3268 0.063 Uiso 1 1 calc R U . . .
C37 C 0.0690(2) 1.0028(10) 0.3561(3) 0.151(3) Uani 1 1 d . . . . .
H37A H 0.0719 1.1193 0.3673 0.181 Uiso 1 1 calc R U . . .
H37B H 0.0946 0.9446 0.3787 0.181 Uiso 1 1 calc R U . . .
Cl1 Cl 0.02631(4) 0.92016(18) 0.36811(6) 0.1067(4) Uani 1 1 d . . . . .
Cl2 Cl 0.06669(7) 0.9931(3) 0.29022(8) 0.1730(9) Uani 1 1 d . . . . .
F1 F -0.01162(7) 0.4126(4) 0.16487(12) 0.1242(11) Uani 1 1 d . . . . .
N1 N 0.22835(7) 0.5957(3) 0.31437(8) 0.0423(6) Uani 1 1 d . . . . .
N2 N 0.19559(9) 0.6010(4) 0.17135(10) 0.0573(7) Uani 1 1 d . . . . .
N3 N 0.14467(7) 0.3983(3) 0.39321(8) 0.0327(5) Uani 1 1 d . . . . .
N4 N 0.15462(7) 0.2297(3) 0.38583(8) 0.0337(5) Uani 1 1 d . . . . .
N5 N 0.31880(8) 0.5459(4) 0.30097(10) 0.0602(8) Uani 1 1 d . . . . .
O1 O 0.15910(6) 0.6613(2) 0.36747(7) 0.0394(5) Uani 1 1 d . . . . .
O2 O 0.28124(7) 0.6390(4) 0.27468(8) 0.0686(7) Uani 1 1 d . . . . .
O3 O 0.48287(7) 0.2394(3) 0.47781(10) 0.0701(7) 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 1.472(3) . ?
C1 C2 1.515(3) . ?
C1 C19 1.553(3) . ?
C1 H1 0.9800 . ?
C2 C7 1.391(4) . ?
C2 C3 1.394(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.508(4) . ?
C8 C29 1.528(4) . ?
C8 C9 1.537(4) . ?
C8 H8 0.9800 . ?
C9 N1 1.393(3) . ?
C9 O2 1.457(4) . ?
C9 H9 0.9800 . ?
C10 N1 1.441(3) . ?
C10 C11 1.491(4) . ?
C10 C22 1.551(4) . ?
C10 H10 0.9800 . ?
C11 N2 1.134(3) . ?
C12 C17 1.377(4) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 N3 1.430(3) . ?
C18 O1 1.214(3) . ?
C18 N3 1.369(3) . ?
C18 C19 1.525(3) . ?
C19 C20 1.501(3) . ?
C19 C22 1.562(3) . ?
C20 N4 1.281(3) . ?
C20 C21 1.487(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.505(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.376(4) . ?
C23 C28 1.383(4) . ?
C24 C25 1.383(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.345(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.358(6) . ?
C26 F1 1.360(4) . ?
C27 C28 1.387(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 N5 1.281(4) . ?
C29 C30 1.468(4) . ?
C30 C31 1.389(4) . ?
C30 C36 1.405(4) . ?
C31 C32 1.387(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.377(4) . ?
C32 H32 0.9300 . ?
C33 O3 1.366(4) . ?
C33 C35 1.387(4) . ?
C34 O3 1.421(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.360(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 Cl2 1.697(7) . ?
C37 Cl1 1.699(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
N3 N4 1.416(3) . ?
N5 O2 1.412(4) . ?

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 C2 108.3(2) . . ?
N1 C1 C19 101.85(19) . . ?
C2 C1 C19 116.2(2) . . ?
N1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C19 C1 H1 110.0 . . ?
C7 C2 C3 119.0(2) . . ?
C7 C2 C1 117.9(2) . . ?
C3 C2 C1 123.0(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 118.9(2) . . ?
C2 C7 C8 119.9(2) . . ?
C6 C7 C8 121.2(2) . . ?
C7 C8 C29 116.8(2) . . ?
C7 C8 C9 113.5(2) . . ?
C29 C8 C9 99.9(2) . . ?
C7 C8 H8 108.7 . . ?
C29 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
N1 C9 O2 112.2(2) . . ?
N1 C9 C8 113.0(2) . . ?
O2 C9 C8 104.2(2) . . ?
N1 C9 H9 109.1 . . ?
O2 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
N1 C10 C11 115.2(2) . . ?
N1 C10 C22 104.65(19) . . ?
C11 C10 C22 108.9(2) . . ?
N1 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C22 C10 H10 109.3 . . ?
N2 C11 C10 177.4(3) . . ?
C17 C12 C13 119.3(3) . . ?
C17 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C12 C17 C16 120.6(2) . . ?
C12 C17 N3 120.0(2) . . ?
C16 C17 N3 119.4(2) . . ?
O1 C18 N3 126.4(2) . . ?
O1 C18 C19 128.6(2) . . ?
N3 C18 C19 105.0(2) . . ?
C20 C19 C18 101.35(19) . . ?
C20 C19 C1 115.7(2) . . ?
C18 C19 C1 113.47(19) . . ?
C20 C19 C22 114.50(19) . . ?
C18 C19 C22 111.6(2) . . ?
C1 C19 C22 100.75(19) . . ?
N4 C20 C21 121.1(2) . . ?
N4 C20 C19 112.9(2) . . ?
C21 C20 C19 125.9(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 115.9(2) . . ?
C23 C22 C19 118.3(2) . . ?
C10 C22 C19 102.12(18) . . ?
C23 C22 H22 106.6 . . ?
C10 C22 H22 106.6 . . ?
C19 C22 H22 106.6 . . ?
C24 C23 C28 117.9(3) . . ?
C24 C23 C22 119.0(3) . . ?
C28 C23 C22 123.1(3) . . ?
C23 C24 C25 121.3(4) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 118.7(4) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 122.6(3) . . ?
C25 C26 F1 119.3(4) . . ?
C27 C26 F1 118.0(4) . . ?
C26 C27 C28 118.3(4) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C23 C28 C27 121.1(3) . . ?
C23 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
N5 C29 C30 118.0(3) . . ?
N5 C29 C8 113.1(3) . . ?
C30 C29 C8 128.9(2) . . ?
C31 C30 C36 116.7(3) . . ?
C31 C30 C29 123.0(3) . . ?
C36 C30 C29 120.3(3) . . ?
C32 C31 C30 121.8(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
O3 C33 C32 124.9(3) . . ?
O3 C33 C35 115.7(3) . . ?
C32 C33 C35 119.4(3) . . ?
O3 C34 H34A 109.5 . . ?
O3 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O3 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C33 120.4(3) . . ?
C36 C35 H35 119.8 . . ?
C33 C35 H35 119.8 . . ?
C35 C36 C30 121.8(3) . . ?
C35 C36 H36 119.1 . . ?
C30 C36 H36 119.1 . . ?
Cl2 C37 Cl1 115.3(3) . . ?
Cl2 C37 H37A 108.5 . . ?
Cl1 C37 H37A 108.5 . . ?
Cl2 C37 H37B 108.5 . . ?
Cl1 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C9 N1 C10 121.7(2) . . ?
C9 N1 C1 123.3(2) . . ?
C10 N1 C1 112.4(2) . . ?
C18 N3 N4 112.93(19) . . ?
C18 N3 C17 126.3(2) . . ?
N4 N3 C17 118.32(19) . . ?
C20 N4 N3 107.77(19) . . ?
C29 N5 O2 109.9(3) . . ?
N5 O2 C9 108.85(19) . . ?
C33 O3 C34 117.7(3) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_1l
_database_code_depnum_ccdc_archive 'CCDC 1937487'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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         'C34 H25 N5 O5'
_chemical_formula_sum            'C34 H25 N5 O5'
_chemical_formula_weight         583.59

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

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

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

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

_cell_length_a                   9.5329(6)
_cell_length_b                   12.0116(9)
_cell_length_c                   26.3133(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.348(2)
_cell_angle_gamma                90
_cell_volume                     3010.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.982
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33168
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.549
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6907
_reflns_number_gt                4276
_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)+(0.1001P)²+2.1059P] 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         6907
_refine_ls_number_parameters     405
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2196
_refine_ls_wR_factor_gt          0.1962
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.086
_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 -0.0533(3) 0.9780(2) 0.24240(11) 0.0428(7) Uani 1 1 d . . . . .
C2 C -0.0347(4) 1.0022(3) 0.29364(12) 0.0593(9) Uani 1 1 d . . . . .
H2 H -0.0944 0.9729 0.3173 0.071 Uiso 1 1 calc R U . . .
C3 C 0.0748(4) 1.0710(3) 0.30849(13) 0.0654(10) Uani 1 1 d . . . . .
H3 H 0.0889 1.0890 0.3427 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1633(4) 1.1133(3) 0.27365(13) 0.0572(8) Uani 1 1 d . . . . .
H4 H 0.2377 1.1585 0.2847 0.069 Uiso 1 1 calc R U . . .
C5 C 0.1442(3) 1.0902(2) 0.22225(11) 0.0435(7) Uani 1 1 d . . . . .
H5 H 0.2050 1.1194 0.1989 0.052 Uiso 1 1 calc R U . . .
C6 C 0.0338(3) 1.0231(2) 0.20622(10) 0.0358(6) Uani 1 1 d . . . . .
C7 C -0.0202(3) 0.9851(2) 0.15452(10) 0.0360(6) Uani 1 1 d . . . . .
C8 C -0.1371(3) 0.9025(2) 0.16741(13) 0.0448(7) Uani 1 1 d . . . . .
C9 C -0.0895(3) 1.0793(2) 0.12078(10) 0.0396(6) Uani 1 1 d . . . . .
H9 H -0.1448 1.0396 0.0943 0.048 Uiso 1 1 calc R U . . .
C10 C -0.1945(3) 1.1539(2) 0.14598(10) 0.0395(6) Uani 1 1 d . . . . .
C11 C -0.3335(3) 1.1198(3) 0.14334(13) 0.0571(8) Uani 1 1 d . . . . .
H11 H -0.3568 1.0542 0.1262 0.069 Uiso 1 1 calc R U . . .
C12 C -0.4379(3) 1.1794(3) 0.16509(14) 0.0620(9) Uani 1 1 d . . . . .
H12 H -0.5299 1.1534 0.1642 0.074 Uiso 1 1 calc R U . . .
C13 C -0.4034(3) 1.2784(2) 0.18822(11) 0.0462(7) Uani 1 1 d . . . . .
C14 C -0.2672(3) 1.3157(3) 0.19236(13) 0.0568(8) Uani 1 1 d . . . . .
H14 H -0.2454 1.3826 0.2086 0.068 Uiso 1 1 calc R U . . .
C15 C -0.1629(3) 1.2511(3) 0.17173(12) 0.0507(8) Uani 1 1 d . . . . .
H15 H -0.0698 1.2740 0.1754 0.061 Uiso 1 1 calc R U . . .
C16 C 0.0866(3) 0.9416(2) 0.11701(10) 0.0370(6) Uani 1 1 d . . . . .
H16 H 0.0363 0.9067 0.0880 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2019(3) 0.8650(2) 0.13652(10) 0.0356(6) Uani 1 1 d . . . . .
C18 C 0.1782(3) 0.7853(2) 0.17327(11) 0.0439(7) Uani 1 1 d . . . . .
H18 H 0.0891 0.7779 0.1860 0.053 Uiso 1 1 calc R U . . .
C19 C 0.2860(3) 0.7162(3) 0.19137(12) 0.0509(7) Uani 1 1 d . . . . .
H19 H 0.2683 0.6615 0.2153 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4175(3) 0.7288(3) 0.17397(12) 0.0538(8) Uani 1 1 d . . . . .
H20 H 0.4904 0.6838 0.1865 0.065 Uiso 1 1 calc R U . . .
C21 C 0.4429(3) 0.8091(3) 0.13734(11) 0.0496(7) Uani 1 1 d . . . . .
H21 H 0.5337 0.8188 0.1264 0.060 Uiso 1 1 calc R U . . .
C22 C 0.3354(3) 0.8749(2) 0.11676(10) 0.0396(6) Uani 1 1 d . . . . .
C23 C 0.3602(3) 0.9512(2) 0.07216(10) 0.0405(6) Uani 1 1 d . . . . .
H23 H 0.4533 0.9853 0.0766 0.049 Uiso 1 1 calc R U . . .
C24 C 0.2501(3) 1.0429(3) 0.06264(10) 0.0454(7) Uani 1 1 d . . . . .
H24 H 0.2976 1.1151 0.0612 0.054 Uiso 1 1 calc R U . . .
C25 C 0.0362(3) 1.1298(2) 0.09259(11) 0.0469(7) Uani 1 1 d . . . . .
H25A H 0.0118 1.1370 0.0562 0.056 Uiso 0.679(18) 1 calc R U P A 1
H25B H 0.0090 1.1253 0.0563 0.056 Uiso 0.321(18) 1 calc R U P A 2
C26 C 0.1060(15) 1.2369(16) 0.1126(7) 0.056(3) Uani 0.679(18) 1 d . . P A 1
N4 N 0.1655(12) 1.3169(6) 0.1248(4) 0.082(3) Uani 0.679(18) 1 d . . P A 1
C26' C 0.071(4) 1.241(4) 0.1013(15) 0.056(3) Uani 0.321(18) 1 d . . P A 2
N4' N 0.103(2) 1.3278(16) 0.1051(9) 0.082(3) Uani 0.321(18) 1 d . . P A 2
C27 C 0.3497(3) 0.8914(3) 0.02139(11) 0.0479(7) Uani 1 1 d . . . . .
C28 C 0.4384(4) 0.7973(3) 0.00553(11) 0.0517(8) Uani 1 1 d . . . . .
C29 C 0.5770(4) 0.7863(3) 0.02312(13) 0.0559(8) Uani 1 1 d . . . . .
H29 H 0.6153 0.8381 0.0460 0.067 Uiso 1 1 calc R U . . .
C30 C 0.6586(4) 0.6990(3) 0.00696(14) 0.0643(9) Uani 1 1 d . . . . .
H30 H 0.7510 0.6912 0.0191 0.077 Uiso 1 1 calc R U . . .
C31 C 0.6002(4) 0.6225(3) -0.02796(13) 0.0640(10) Uani 1 1 d . . . . .
C32 C 0.6452(6) 0.4661(3) -0.08113(17) 0.0958(15) Uani 1 1 d . . . . .
H32A H 0.5596 0.4299 -0.0725 0.144 Uiso 1 1 calc R U . . .
H32B H 0.7163 0.4111 -0.0863 0.144 Uiso 1 1 calc R U . . .
H32C H 0.6295 0.5084 -0.1118 0.144 Uiso 1 1 calc R U . . .
C33 C 0.4661(4) 0.6329(3) -0.04604(13) 0.0666(10) Uani 1 1 d . . . . .
H33 H 0.4289 0.5823 -0.0697 0.080 Uiso 1 1 calc R U . . .
C34 C 0.3839(4) 0.7202(3) -0.02894(13) 0.0650(9) Uani 1 1 d . . . . .
H34 H 0.2911 0.7267 -0.0409 0.078 Uiso 1 1 calc R U . . .
N1 N -0.1534(3) 0.9095(2) 0.21797(10) 0.0529(7) Uani 1 1 d . . . . .
H1 H -0.2185 0.8755 0.2335 0.063 Uiso 1 1 calc R U . . .
N2 N -0.5133(3) 1.3435(3) 0.21119(13) 0.0723(6) Uani 1 1 d . U . . .
N3 N 0.1483(2) 1.04685(18) 0.10069(8) 0.0392(5) Uani 1 1 d . . . . .
N5 N 0.2536(3) 0.9286(3) -0.00889(10) 0.0637(8) Uani 1 1 d . . . . .
O1 O -0.2051(2) 0.8469(2) 0.13717(10) 0.0656(7) Uani 1 1 d . . . . .
O2 O -0.6243(3) 1.2995(2) 0.21905(11) 0.0786(7) Uani 1 1 d . U . . .
O3 O -0.4882(3) 1.4396(2) 0.22331(13) 0.0945(7) Uani 1 1 d . U . . .
O4 O 0.1834(2) 1.0187(2) 0.01318(8) 0.0682(7) Uani 1 1 d . . . . .
O5 O 0.6898(3) 0.5382(2) -0.04109(11) 0.0830(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 C2 1.384(4) . ?
C1 N1 1.397(4) . ?
C1 C6 1.398(4) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 C16 1.538(4) . ?
C7 C8 1.541(4) . ?
C7 C9 1.568(4) . ?
C8 O1 1.207(4) . ?
C8 N1 1.348(4) . ?
C9 C10 1.516(4) . ?
C9 C25 1.557(4) . ?
C9 H9 0.9800 . ?
C10 C15 1.377(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 N2 1.458(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.465(3) . ?
C16 C17 1.507(4) . ?
C16 H16 0.9800 . ?
C17 C18 1.386(4) . ?
C17 C22 1.399(4) . ?
C18 C19 1.389(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.361(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.516(4) . ?
C23 C27 1.516(4) . ?
C23 C24 1.535(4) . ?
C23 H23 0.9800 . ?
C24 N3 1.424(3) . ?
C24 O4 1.454(4) . ?
C24 H24 0.9800 . ?
C25 C26' 1.39(5) . ?
C25 N3 1.470(4) . ?
C25 C26 1.53(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 N4 1.15(2) . ?
C26' N4' 1.09(5) . ?
C27 N5 1.270(4) . ?
C27 C28 1.482(4) . ?
C28 C34 1.382(5) . ?
C28 C29 1.388(5) . ?
C29 C30 1.383(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.399(5) . ?
C30 H30 0.9300 . ?
C31 C33 1.352(5) . ?
C31 O5 1.378(4) . ?
C32 O5 1.415(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.394(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?
N2 O2 1.208(4) . ?
N2 O3 1.219(4) . ?
N5 O4 1.411(4) . ?

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
C2 C1 N1 129.1(3) . . ?
C2 C1 C6 121.8(3) . . ?
N1 C1 C6 109.2(2) . . ?
C3 C2 C1 117.9(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 133.0(2) . . ?
C1 C6 C7 107.9(2) . . ?
C6 C7 C16 118.1(2) . . ?
C6 C7 C8 102.7(2) . . ?
C16 C7 C8 115.2(2) . . ?
C6 C7 C9 114.4(2) . . ?
C16 C7 C9 99.0(2) . . ?
C8 C7 C9 107.3(2) . . ?
O1 C8 N1 127.2(3) . . ?
O1 C8 C7 125.8(3) . . ?
N1 C8 C7 106.9(2) . . ?
C10 C9 C25 120.9(2) . . ?
C10 C9 C7 116.7(2) . . ?
C25 C9 C7 103.7(2) . . ?
C10 C9 H9 104.6 . . ?
C25 C9 H9 104.6 . . ?
C7 C9 H9 104.6 . . ?
C15 C10 C11 117.7(3) . . ?
C15 C10 C9 125.5(2) . . ?
C11 C10 C9 116.8(3) . . ?
C12 C11 C10 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 N2 119.1(3) . . ?
C14 C13 N2 119.0(3) . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C14 121.3(3) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
N3 C16 C17 109.3(2) . . ?
N3 C16 C7 100.3(2) . . ?
C17 C16 C7 118.8(2) . . ?
N3 C16 H16 109.3 . . ?
C17 C16 H16 109.3 . . ?
C7 C16 H16 109.3 . . ?
C18 C17 C22 119.6(3) . . ?
C18 C17 C16 121.5(2) . . ?
C22 C17 C16 118.9(2) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 118.4(3) . . ?
C21 C22 C23 120.7(2) . . ?
C17 C22 C23 120.8(2) . . ?
C22 C23 C27 112.9(2) . . ?
C22 C23 C24 115.6(2) . . ?
C27 C23 C24 100.1(2) . . ?
C22 C23 H23 109.3 . . ?
C27 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
N3 C24 O4 110.5(2) . . ?
N3 C24 C23 113.0(2) . . ?
O4 C24 C23 105.9(2) . . ?
N3 C24 H24 109.1 . . ?
O4 C24 H24 109.1 . . ?
C23 C24 H24 109.1 . . ?
C26' C25 N3 117.3(13) . . ?
N3 C25 C26 102.5(6) . . ?
C26' C25 C9 118.6(18) . . ?
N3 C25 C9 103.6(2) . . ?
C26 C25 C9 119.7(7) . . ?
N3 C25 H25A 110.1 . . ?
C26 C25 H25A 110.1 . . ?
C9 C25 H25A 110.1 . . ?
C26' C25 H25B 105.4 . . ?
N3 C25 H25B 105.4 . . ?
C9 C25 H25B 105.4 . . ?
N4 C26 C25 174.9(16) . . ?
N4' C26' C25 175(4) . . ?
N5 C27 C28 119.8(3) . . ?
N5 C27 C23 114.0(3) . . ?
C28 C27 C23 126.3(3) . . ?
C34 C28 C29 118.8(3) . . ?
C34 C28 C27 119.5(3) . . ?
C29 C28 C27 121.7(3) . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.1(3) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C33 C31 O5 124.5(3) . . ?
C33 C31 C30 121.0(3) . . ?
O5 C31 C30 114.4(4) . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 C34 119.5(4) . . ?
C31 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C28 C34 C33 121.0(4) . . ?
C28 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C8 N1 C1 112.7(2) . . ?
C8 N1 H1 123.6 . . ?
C1 N1 H1 123.6 . . ?
O2 N2 O3 122.3(3) . . ?
O2 N2 C13 119.0(3) . . ?
O3 N2 C13 118.6(3) . . ?
C24 N3 C16 118.1(2) . . ?
C24 N3 C25 115.7(2) . . ?
C16 N3 C25 109.2(2) . . ?
C27 N5 O4 110.7(2) . . ?
N5 O4 C24 108.9(2) . . ?
C31 O5 C32 117.8(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.19 3.045(3) 173.3 2_445

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.056


####################################################################### 
# 
# 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_3n
_database_code_depnum_ccdc_archive 'CCDC 1937508'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 Br N5 O2'
_chemical_formula_sum            'C36 H28 Br N5 O2'
_chemical_formula_weight         642.54

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'
Br Br -0.2901 2.4595 '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                   7.9473(8)
_cell_length_b                   12.8859(14)
_cell_length_c                   15.2264(16)
_cell_angle_alpha                93.496(3)
_cell_angle_beta                 101.326(3)
_cell_angle_gamma                98.939(3)
_cell_volume                     1503.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7176
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.409
_shelx_estimated_absorpt_T_min   0.728
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21114
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         25.998
_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             5892
_reflns_number_gt                3847
_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)+(0.1262P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5892
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Br1 Br 0.7773(3) 0.05994(19) 0.16068(17) 0.0735(9) Uani 0.536(16) 1 d . . P A 1
Br1' Br 0.7442(12) 0.0663(3) 0.1350(9) 0.1418(16) Uani 0.464(16) 1 d . . P A 2
C1 C 0.0906(4) 0.2870(3) 0.43840(19) 0.0499(8) Uani 1 1 d . . . . .
H1 H -0.0199 0.2757 0.4587 0.060 Uiso 1 1 calc R U . . .
C2 C 0.1197(4) 0.1875(2) 0.39016(18) 0.0454(7) Uani 1 1 d . . . . .
H2 H 0.0080 0.1521 0.3532 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1934(4) 0.1107(2) 0.45018(18) 0.0408(7) Uani 1 1 d . . . . .
C4 C 0.1499(4) 0.0027(3) 0.4254(2) 0.0484(8) Uani 1 1 d . . . . .
H4 H 0.0738 -0.0220 0.3710 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2177(4) -0.0684(2) 0.4802(2) 0.0491(8) Uani 1 1 d . . . . .
H5 H 0.1896 -0.1404 0.4625 0.059 Uiso 1 1 calc R U . . .
C6 C 0.3267(4) -0.0321(3) 0.5610(2) 0.0516(8) Uani 1 1 d . . . . .
H6 H 0.3733 -0.0798 0.5981 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3686(4) 0.0747(2) 0.58793(19) 0.0452(7) Uani 1 1 d . . . . .
H7 H 0.4417 0.0980 0.6434 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3026(3) 0.1478(2) 0.53314(17) 0.0377(6) Uani 1 1 d . . . . .
C9 C 0.3518(3) 0.2641(2) 0.56014(16) 0.0367(6) Uani 1 1 d . . . . .
H9 H 0.4669 0.2869 0.5469 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2111(4) 0.4167(2) 0.56732(17) 0.0394(7) Uani 1 1 d . . . . .
H10 H 0.0939 0.4047 0.5801 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2394(4) 0.5176(3) 0.5270(2) 0.0478(7) Uani 1 1 d . . . . .
C12 C 0.0435(4) 0.1715(3) 0.8502(2) 0.0601(9) Uani 1 1 d . . . . .
H12 H -0.0294 0.1611 0.7935 0.072 Uiso 1 1 calc R U . . .
C13 C -0.0227(6) 0.1537(4) 0.9262(3) 0.0881(14) Uani 1 1 d . . . . .
H13 H -0.1416 0.1305 0.9198 0.106 Uiso 1 1 calc R U . . .
C14 C 0.0788(7) 0.1687(5) 1.0089(3) 0.1085(18) Uani 1 1 d . . . . .
H14 H 0.0306 0.1572 1.0592 0.130 Uiso 1 1 calc R U . . .
C15 C 0.2533(7) 0.2012(5) 1.0184(3) 0.1032(17) Uani 1 1 d . . . . .
H15 H 0.3249 0.2109 1.0754 0.124 Uiso 1 1 calc R U . . .
C16 C 0.3249(5) 0.2197(3) 0.9440(2) 0.0754(12) Uani 1 1 d . . . . .
H16 H 0.4441 0.2421 0.9509 0.090 Uiso 1 1 calc R U . . .
C17 C 0.2192(4) 0.2048(2) 0.86004(18) 0.0440(7) Uani 1 1 d . . . . .
C18 C 0.2152(3) 0.2490(2) 0.70084(17) 0.0341(6) Uani 1 1 d . . . . .
C19 C 0.3626(3) 0.3010(2) 0.65971(16) 0.0347(6) Uani 1 1 d . . . . .
C20 C 0.5179(4) 0.2872(2) 0.72845(18) 0.0395(7) Uani 1 1 d . . . . .
C21 C 0.7023(4) 0.3185(3) 0.7203(2) 0.0610(9) Uani 1 1 d . . . . .
H21A H 0.7783 0.3154 0.7771 0.091 Uiso 1 1 calc R U . . .
H21B H 0.7195 0.3891 0.7030 0.091 Uiso 1 1 calc R U . . .
H21C H 0.7280 0.2711 0.6755 0.091 Uiso 1 1 calc R U . . .
C22 C 0.3469(3) 0.4205(2) 0.65544(17) 0.0373(6) Uani 1 1 d . . . . .
H22 H 0.4581 0.4583 0.6464 0.045 Uiso 1 1 calc R U . . .
C23 C 0.3080(4) 0.4726(2) 0.73959(17) 0.0379(6) Uani 1 1 d . . . . .
C24 C 0.4442(4) 0.5084(2) 0.81291(19) 0.0479(7) Uani 1 1 d . . . . .
H24 H 0.5577 0.5042 0.8079 0.057 Uiso 1 1 calc R U . . .
C25 C 0.4141(5) 0.5501(3) 0.8927(2) 0.0564(9) Uani 1 1 d . . . . .
H25 H 0.5073 0.5722 0.9410 0.068 Uiso 1 1 calc R U . . .
C26 C 0.2465(5) 0.5597(3) 0.9023(2) 0.0580(9) Uani 1 1 d . . . . .
C27 C 0.2128(7) 0.6046(5) 0.9895(3) 0.1053(17) Uani 1 1 d . . . . .
H27A H 0.2422 0.6801 0.9945 0.158 Uiso 1 1 calc R U . . .
H27B H 0.2829 0.5778 1.0389 0.158 Uiso 1 1 calc R U . . .
H27C H 0.0919 0.5845 0.9908 0.158 Uiso 1 1 calc R U . . .
C28 C 0.1130(5) 0.5269(3) 0.8288(2) 0.0618(9) Uani 1 1 d . . . . .
H28 H 0.0001 0.5339 0.8331 0.074 Uiso 1 1 calc R U . . .
C29 C 0.1416(4) 0.4838(2) 0.7487(2) 0.0491(8) Uani 1 1 d . . . . .
H29 H 0.0481 0.4622 0.7004 0.059 Uiso 1 1 calc R U . . .
C30 C 0.2296(5) 0.2397(3) 0.32854(18) 0.0511(8) Uani 1 1 d . . . . .
C31 C 0.3555(4) 0.1942(2) 0.28572(18) 0.0478(8) Uani 1 1 d . . . . .
C32 C 0.5149(5) 0.2560(3) 0.2851(2) 0.0606(9) Uani 1 1 d . . . . .
H32 H 0.5401 0.3247 0.3124 0.073 Uiso 1 1 calc R U . . .
C33 C 0.6358(5) 0.2178(3) 0.2450(2) 0.0662(10) Uani 1 1 d . . . . .
H33 H 0.7412 0.2606 0.2445 0.079 Uiso 1 1 calc R U . . .
C34 C 0.6006(5) 0.1166(3) 0.2057(2) 0.0625(9) Uani 1 1 d . . . . .
C35 C 0.4435(5) 0.0524(3) 0.2057(2) 0.0620(9) Uani 1 1 d . . . . .
H35 H 0.4200 -0.0164 0.1785 0.074 Uiso 1 1 calc R U . . .
C36 C 0.3224(5) 0.0911(3) 0.2462(2) 0.0557(8) Uani 1 1 d . . . . .
H36 H 0.2177 0.0478 0.2470 0.067 Uiso 1 1 calc R U . . .
N1 N 0.2330(3) 0.32752(19) 0.51125(14) 0.0442(6) Uani 1 1 d . . . . .
N2 N 0.2617(4) 0.5967(3) 0.4986(2) 0.0695(9) Uani 1 1 d . . . . .
N3 N 0.4779(3) 0.2483(2) 0.79838(15) 0.0446(6) Uani 1 1 d . . . . .
N4 N 0.2944(3) 0.22632(19) 0.78436(14) 0.0385(6) Uani 1 1 d . . . . .
N5 N 0.2063(5) 0.3338(2) 0.31648(17) 0.0669(9) Uani 1 1 d . . . . .
O1 O 0.0602(2) 0.23581(16) 0.66882(13) 0.0438(5) Uani 1 1 d . . . . .
O2 O 0.0873(4) 0.36024(19) 0.37002(14) 0.0675(7) 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
Br1 C34 1.900(5) . ?
Br1' C34 1.874(5) . ?
C1 N1 1.427(4) . ?
C1 O2 1.446(4) . ?
C1 C2 1.511(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.496(4) . ?
C2 C30 1.520(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.391(4) . ?
C3 C8 1.394(4) . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.500(4) . ?
C9 N1 1.466(4) . ?
C9 C19 1.543(3) . ?
C9 H9 0.9800 . ?
C10 N1 1.443(4) . ?
C10 C11 1.476(4) . ?
C10 C22 1.541(4) . ?
C10 H10 0.9800 . ?
C11 N2 1.134(4) . ?
C12 C17 1.371(5) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.341(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C17 N4 1.421(4) . ?
C18 O1 1.214(3) . ?
C18 N4 1.374(3) . ?
C18 C19 1.519(4) . ?
C19 C20 1.495(4) . ?
C19 C22 1.568(4) . ?
C20 N3 1.278(4) . ?
C20 C21 1.490(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.517(4) . ?
C22 H22 0.9800 . ?
C23 C29 1.385(4) . ?
C23 C24 1.392(4) . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(5) . ?
C25 H25 0.9300 . ?
C26 C28 1.376(5) . ?
C26 C27 1.505(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.383(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N5 1.274(4) . ?
C30 C31 1.471(5) . ?
C31 C36 1.389(4) . ?
C31 C32 1.390(5) . ?
C32 C33 1.371(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.386(5) . ?
C35 C36 1.378(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N3 N4 1.412(3) . ?
N5 O2 1.430(4) . ?

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 O2 108.4(3) . . ?
N1 C1 C2 111.6(2) . . ?
O2 C1 C2 102.8(2) . . ?
N1 C1 H1 111.3 . . ?
O2 C1 H1 111.3 . . ?
C2 C1 H1 111.3 . . ?
C3 C2 C1 115.0(2) . . ?
C3 C2 C30 118.4(3) . . ?
C1 C2 C30 97.6(3) . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C30 C2 H2 108.4 . . ?
C4 C3 C8 119.6(3) . . ?
C4 C3 C2 120.8(2) . . ?
C8 C3 C2 119.6(3) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 118.4(3) . . ?
C7 C8 C9 121.4(2) . . ?
C3 C8 C9 120.1(2) . . ?
N1 C9 C8 114.2(2) . . ?
N1 C9 C19 103.4(2) . . ?
C8 C9 C19 116.9(2) . . ?
N1 C9 H9 107.3 . . ?
C8 C9 H9 107.3 . . ?
C19 C9 H9 107.3 . . ?
N1 C10 C11 113.3(2) . . ?
N1 C10 C22 105.4(2) . . ?
C11 C10 C22 109.9(2) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C22 C10 H10 109.4 . . ?
N2 C11 C10 177.8(3) . . ?
C17 C12 C13 118.6(3) . . ?
C17 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 120.0(3) . . ?
C16 C17 N4 118.9(3) . . ?
C12 C17 N4 121.1(3) . . ?
O1 C18 N4 127.4(3) . . ?
O1 C18 C19 127.3(2) . . ?
N4 C18 C19 105.2(2) . . ?
C20 C19 C18 101.1(2) . . ?
C20 C19 C9 119.1(2) . . ?
C18 C19 C9 115.5(2) . . ?
C20 C19 C22 111.3(2) . . ?
C18 C19 C22 107.6(2) . . ?
C9 C19 C22 102.1(2) . . ?
N3 C20 C21 122.0(3) . . ?
N3 C20 C19 113.1(2) . . ?
C21 C20 C19 124.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 116.9(2) . . ?
C23 C22 C19 114.5(2) . . ?
C10 C22 C19 101.6(2) . . ?
C23 C22 H22 107.8 . . ?
C10 C22 H22 107.8 . . ?
C19 C22 H22 107.8 . . ?
C29 C23 C24 117.6(3) . . ?
C29 C23 C22 123.2(2) . . ?
C24 C23 C22 119.2(3) . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 121.1(3) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C28 C26 C25 117.3(3) . . ?
C28 C26 C27 121.4(4) . . ?
C25 C26 C27 121.3(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 122.0(3) . . ?
C26 C28 H28 119.0 . . ?
C29 C28 H28 119.0 . . ?
C28 C29 C23 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C23 C29 H29 119.7 . . ?
N5 C30 C31 119.7(3) . . ?
N5 C30 C2 113.0(3) . . ?
C31 C30 C2 127.4(3) . . ?
C36 C31 C32 118.3(3) . . ?
C36 C31 C30 122.6(3) . . ?
C32 C31 C30 119.1(3) . . ?
C33 C32 C31 121.4(3) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C33 C32 119.6(3) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.6(3) . . ?
C33 C34 Br1' 121.6(3) . . ?
C35 C34 Br1' 117.2(3) . . ?
C33 C34 Br1 119.3(3) . . ?
C35 C34 Br1 119.9(3) . . ?
C36 C35 C34 119.6(3) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C31 120.5(3) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C1 N1 C10 116.1(2) . . ?
C1 N1 C9 124.9(2) . . ?
C10 N1 C9 112.25(19) . . ?
C20 N3 N4 107.9(2) . . ?
C18 N4 N3 112.3(2) . . ?
C18 N4 C17 128.6(2) . . ?
N3 N4 C17 117.8(2) . . ?
C30 N5 O2 108.1(3) . . ?
N5 O2 C1 106.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 42.5(4) . . . . ?
O2 C1 C2 C3 158.5(2) . . . . ?
N1 C1 C2 C30 -83.8(3) . . . . ?
O2 C1 C2 C30 32.2(3) . . . . ?
C1 C2 C3 C4 147.8(3) . . . . ?
C30 C2 C3 C4 -97.5(3) . . . . ?
C1 C2 C3 C8 -30.2(4) . . . . ?
C30 C2 C3 C8 84.5(3) . . . . ?
C8 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C4 C5 179.8(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
C4 C3 C8 C7 1.6(4) . . . . ?
C2 C3 C8 C7 179.6(3) . . . . ?
C4 C3 C8 C9 179.4(2) . . . . ?
C2 C3 C8 C9 -2.6(4) . . . . ?
C7 C8 C9 N1 -161.6(2) . . . . ?
C3 C8 C9 N1 20.6(3) . . . . ?
C7 C8 C9 C19 -40.8(4) . . . . ?
C3 C8 C9 C19 141.4(2) . . . . ?
C17 C12 C13 C14 0.5(7) . . . . ?
C12 C13 C14 C15 -0.9(9) . . . . ?
C13 C14 C15 C16 0.8(10) . . . . ?
C14 C15 C16 C17 -0.3(8) . . . . ?
C15 C16 C17 C12 -0.1(6) . . . . ?
C15 C16 C17 N4 178.7(4) . . . . ?
C13 C12 C17 C16 0.0(6) . . . . ?
C13 C12 C17 N4 -178.8(3) . . . . ?
O1 C18 C19 C20 -177.0(3) . . . . ?
N4 C18 C19 C20 6.8(3) . . . . ?
O1 C18 C19 C9 -47.0(4) . . . . ?
N4 C18 C19 C9 136.7(2) . . . . ?
O1 C18 C19 C22 66.2(3) . . . . ?
N4 C18 C19 C22 -110.0(2) . . . . ?
N1 C9 C19 C20 -156.7(2) . . . . ?
C8 C9 C19 C20 76.9(3) . . . . ?
N1 C9 C19 C18 82.7(3) . . . . ?
C8 C9 C19 C18 -43.6(3) . . . . ?
N1 C9 C19 C22 -33.7(2) . . . . ?
C8 C9 C19 C22 -160.0(2) . . . . ?
C18 C19 C20 N3 -6.1(3) . . . . ?
C9 C19 C20 N3 -133.7(3) . . . . ?
C22 C19 C20 N3 107.9(3) . . . . ?
C18 C19 C20 C21 176.2(3) . . . . ?
C9 C19 C20 C21 48.6(4) . . . . ?
C22 C19 C20 C21 -69.8(4) . . . . ?
N1 C10 C22 C23 -154.6(2) . . . . ?
C11 C10 C22 C23 83.0(3) . . . . ?
N1 C10 C22 C19 -29.3(3) . . . . ?
C11 C10 C22 C19 -151.7(2) . . . . ?
C20 C19 C22 C23 -66.4(3) . . . . ?
C18 C19 C22 C23 43.5(3) . . . . ?
C9 C19 C22 C23 165.4(2) . . . . ?
C20 C19 C22 C10 166.6(2) . . . . ?
C18 C19 C22 C10 -83.5(2) . . . . ?
C9 C19 C22 C10 38.5(2) . . . . ?
C10 C22 C23 C29 22.4(4) . . . . ?
C19 C22 C23 C29 -96.2(3) . . . . ?
C10 C22 C23 C24 -159.6(2) . . . . ?
C19 C22 C23 C24 81.8(3) . . . . ?
C29 C23 C24 C25 2.3(4) . . . . ?
C22 C23 C24 C25 -175.8(3) . . . . ?
C23 C24 C25 C26 -1.3(5) . . . . ?
C24 C25 C26 C28 -0.6(5) . . . . ?
C24 C25 C26 C27 179.6(4) . . . . ?
C25 C26 C28 C29 1.4(5) . . . . ?
C27 C26 C28 C29 -178.8(4) . . . . ?
C26 C28 C29 C23 -0.3(5) . . . . ?
C24 C23 C29 C28 -1.5(5) . . . . ?
C22 C23 C29 C28 176.5(3) . . . . ?
C3 C2 C30 N5 -146.4(3) . . . . ?
C1 C2 C30 N5 -22.6(3) . . . . ?
C3 C2 C30 C31 32.3(4) . . . . ?
C1 C2 C30 C31 156.1(3) . . . . ?
N5 C30 C31 C36 -138.6(3) . . . . ?
C2 C30 C31 C36 42.8(4) . . . . ?
N5 C30 C31 C32 41.9(4) . . . . ?
C2 C30 C31 C32 -136.7(3) . . . . ?
C36 C31 C32 C33 1.4(5) . . . . ?
C30 C31 C32 C33 -179.1(3) . . . . ?
C31 C32 C33 C34 -0.9(5) . . . . ?
C32 C33 C34 C35 0.3(6) . . . . ?
C32 C33 C34 Br1' 170.6(6) . . . . ?
C32 C33 C34 Br1 -173.9(3) . . . . ?
C33 C34 C35 C36 -0.4(6) . . . . ?
Br1' C34 C35 C36 -171.0(5) . . . . ?
Br1 C34 C35 C36 173.8(3) . . . . ?
C34 C35 C36 C31 1.0(5) . . . . ?
C32 C31 C36 C35 -1.4(5) . . . . ?
C30 C31 C36 C35 179.1(3) . . . . ?
O2 C1 N1 C10 73.3(3) . . . . ?
C2 C1 N1 C10 -174.2(2) . . . . ?
O2 C1 N1 C9 -138.0(3) . . . . ?
C2 C1 N1 C9 -25.5(4) . . . . ?
C11 C10 N1 C1 -78.6(3) . . . . ?
C22 C10 N1 C1 161.2(2) . . . . ?
C11 C10 N1 C9 128.8(2) . . . . ?
C22 C10 N1 C9 8.7(3) . . . . ?
C8 C9 N1 C1 -5.4(4) . . . . ?
C19 C9 N1 C1 -133.5(3) . . . . ?
C8 C9 N1 C10 144.3(2) . . . . ?
C19 C9 N1 C10 16.3(3) . . . . ?
C21 C20 N3 N4 -179.4(3) . . . . ?
C19 C20 N3 N4 2.8(3) . . . . ?
O1 C18 N4 N3 177.9(3) . . . . ?
C19 C18 N4 N3 -5.9(3) . . . . ?
O1 C18 N4 C17 -15.3(5) . . . . ?
C19 C18 N4 C17 160.9(3) . . . . ?
C20 N3 N4 C18 2.1(3) . . . . ?
C20 N3 N4 C17 -166.2(2) . . . . ?
C16 C17 N4 C18 -157.7(3) . . . . ?
C12 C17 N4 C18 21.1(5) . . . . ?
C16 C17 N4 N3 8.4(4) . . . . ?
C12 C17 N4 N3 -172.7(3) . . . . ?
C31 C30 N5 O2 -176.1(3) . . . . ?
C2 C30 N5 O2 2.7(4) . . . . ?
C30 N5 O2 C1 20.0(3) . . . . ?
N1 C1 O2 N5 84.6(3) . . . . ?
C2 C1 O2 N5 -33.6(3) . . . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.685
_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_2bb
_database_code_depnum_ccdc_archive 'CCDC 1937489'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 Br N3 O4'
_chemical_formula_sum            'C35 H28 Br N3 O4'
_chemical_formula_weight         634.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8593(9)
_cell_length_b                   22.333(2)
_cell_length_c                   15.6805(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.730(3)
_cell_angle_gamma                90
_cell_volume                     3066.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5956
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1304
_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    1.384
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.758
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19933
_diffrn_reflns_av_unetI/netI     0.1322
_diffrn_reflns_av_R_equivalents  0.2940
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.599
_diffrn_reflns_theta_max         20.812
_diffrn_reflns_theta_full        20.812
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3210
_reflns_number_gt                2500
_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)+(0.1657P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3210
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.2362
_refine_ls_wR_factor_gt          0.2088
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.51363(10) 0.63582(4) 0.55462(5) 0.0572(5) Uani 1 1 d . . . . .
C1 C 0.9426(7) 0.4440(3) 0.2517(4) 0.0362(18) Uani 1 1 d . . . . .
C2 C 1.0832(8) 0.4342(4) 0.3038(5) 0.048(2) Uani 1 1 d . . . . .
H2 H 1.1721 0.4272 0.2806 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0821(9) 0.4355(4) 0.3909(6) 0.060(2) Uani 1 1 d . . . . .
H3 H 1.1736 0.4297 0.4276 0.072 Uiso 1 1 calc R U . . .
C4 C 0.9515(9) 0.4451(3) 0.4265(5) 0.050(2) Uani 1 1 d . . . . .
H4 H 0.9545 0.4432 0.4860 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8160(8) 0.4574(3) 0.3734(4) 0.044(2) Uani 1 1 d . . . . .
H5 H 0.7287 0.4664 0.3972 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8104(7) 0.4563(3) 0.2857(4) 0.0311(17) Uani 1 1 d . . . . .
C7 C 0.6841(7) 0.4653(3) 0.2105(4) 0.0278(16) Uani 1 1 d . . . . .
C8 C 0.7624(7) 0.4547(3) 0.1319(5) 0.0375(18) Uani 1 1 d . . . . .
C9 C 0.6060(7) 0.5285(3) 0.2026(4) 0.0304(17) Uani 1 1 d . . . . .
H9 H 0.6705 0.5563 0.1759 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5779(7) 0.5541(3) 0.2878(4) 0.0311(17) Uani 1 1 d . . . . .
C11 C 0.6775(8) 0.5967(3) 0.3300(5) 0.0400(19) Uani 1 1 d . . . . .
H11 H 0.7595 0.6093 0.3039 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6601(8) 0.6203(3) 0.4072(5) 0.042(2) Uani 1 1 d . . . . .
H12 H 0.7283 0.6490 0.4330 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5395(9) 0.6015(3) 0.4474(4) 0.0379(18) Uani 1 1 d . . . . .
C14 C 0.4378(7) 0.5606(3) 0.4083(4) 0.0369(18) Uani 1 1 d . . . . .
H14 H 0.3562 0.5484 0.4350 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4560(8) 0.5375(3) 0.3291(5) 0.0376(18) Uani 1 1 d . . . . .
H15 H 0.3850 0.5101 0.3025 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5430(7) 0.4228(3) 0.2110(4) 0.0321(17) Uani 1 1 d . . . . .
H16 H 0.5180 0.4229 0.2698 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5681(7) 0.3598(3) 0.1879(5) 0.038(2) Uani 1 1 d . . . . .
C18 C 0.6564(9) 0.3235(4) 0.2501(6) 0.065(3) Uani 1 1 d . . . . .
H18 H 0.6938 0.3393 0.3040 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6875(13) 0.2660(4) 0.2320(9) 0.124(6) Uani 1 1 d . . . . .
H19 H 0.7466 0.2425 0.2733 0.149 Uiso 1 1 calc R U . . .
C20 C 0.6308(16) 0.2420(5) 0.1515(11) 0.159(7) Uani 1 1 d . . . . .
H20 H 0.6556 0.2029 0.1384 0.190 Uiso 1 1 calc R U . . .
C21 C 0.5391(11) 0.2753(4) 0.0916(8) 0.110(5) Uani 1 1 d . . . . .
H21 H 0.4983 0.2584 0.0389 0.132 Uiso 1 1 calc R U . . .
C22 C 0.5069(8) 0.3337(4) 0.1088(5) 0.055(2) Uani 1 1 d . . . . .
C23 C 0.4033(8) 0.3708(3) 0.0424(5) 0.040(2) Uani 1 1 d . . . . .
H23 H 0.4573 0.3840 -0.0044 0.048 Uiso 1 1 calc R U . . .
C24 C 0.3335(7) 0.4233(3) 0.0836(5) 0.0375(18) Uani 1 1 d . . . . .
H24 H 0.2980 0.4526 0.0383 0.045 Uiso 1 1 calc R U . . .
C25 C 0.4600(7) 0.5153(3) 0.1379(4) 0.0306(17) Uani 1 1 d . . . . .
H25 H 0.4899 0.5155 0.0802 0.037 Uiso 1 1 calc R U . . .
C26 C 0.3391(8) 0.5634(4) 0.1380(4) 0.0404(19) Uani 1 1 d . . . . .
C27 C 0.0763(9) 0.5855(4) 0.1330(7) 0.072(3) Uani 1 1 d . . . . .
H27A H -0.0196 0.5672 0.1081 0.087 Uiso 1 1 calc R U . . .
H27B H 0.0986 0.6178 0.0954 0.087 Uiso 1 1 calc R U . . .
C28 C 0.0646(12) 0.6094(5) 0.2206(8) 0.100(4) Uani 1 1 d . . . . .
H28A H 0.1574 0.6299 0.2430 0.150 Uiso 1 1 calc R U . . .
H28B H 0.0484 0.5769 0.2582 0.150 Uiso 1 1 calc R U . . .
H28C H -0.0196 0.6369 0.2168 0.150 Uiso 1 1 calc R U . . .
C29 C 0.2583(8) 0.3379(4) 0.0078(5) 0.0416(19) Uani 1 1 d . . . . .
C30 C 0.2335(10) 0.2956(3) -0.0645(6) 0.054(2) Uani 1 1 d . . . . .
C31 C 0.3280(11) 0.2957(4) -0.1274(6) 0.063(2) Uani 1 1 d . . . . .
H31 H 0.4135 0.3204 -0.1218 0.076 Uiso 1 1 calc R U . . .
C32 C 0.2938(16) 0.2587(5) -0.1986(7) 0.089(3) Uani 1 1 d . . . . .
H32 H 0.3565 0.2595 -0.2412 0.107 Uiso 1 1 calc R U . . .
C33 C 0.173(2) 0.2217(6) -0.2082(9) 0.111(5) Uani 1 1 d . . . . .
H33 H 0.1533 0.1969 -0.2563 0.133 Uiso 1 1 calc R U . . .
C34 C 0.0785(15) 0.2209(5) -0.1454(11) 0.103(5) Uani 1 1 d . . . . .
H34 H -0.0055 0.1955 -0.1512 0.123 Uiso 1 1 calc R U . . .
C35 C 0.1085(10) 0.2577(4) -0.0746(7) 0.075(3) Uani 1 1 d . . . . .
H35 H 0.0441 0.2570 -0.0330 0.090 Uiso 1 1 calc R U . . .
N1 N 0.9137(6) 0.4429(3) 0.1621(4) 0.0429(16) Uani 1 1 d . . . . .
H1 H 0.9819 0.4365 0.1295 0.051 Uiso 1 1 d R U . . .
N2 N 0.4164(5) 0.4545(2) 0.1548(4) 0.0328(14) Uani 1 1 d . . . . .
N3 N 0.1475(7) 0.3512(3) 0.0499(5) 0.0537(18) Uani 1 1 d . . . . .
O1 O 0.7066(5) 0.4567(3) 0.0567(3) 0.0535(15) Uani 1 1 d . . . . .
O2 O 0.3673(6) 0.6147(3) 0.1325(4) 0.0550(15) Uani 1 1 d . . . . .
O3 O 0.1998(5) 0.5407(2) 0.1415(3) 0.0499(14) Uani 1 1 d . . . . .
O4 O 0.1975(5) 0.3949(2) 0.1118(3) 0.0476(14) 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
Br1 C13 1.894(7) . ?
C1 C6 1.386(9) . ?
C1 N1 1.390(9) . ?
C1 C2 1.399(10) . ?
C2 C3 1.367(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(9) . ?
C7 C8 1.521(10) . ?
C7 C9 1.568(9) . ?
C7 C16 1.571(9) . ?
C8 O1 1.209(8) . ?
C8 N1 1.378(8) . ?
C9 C10 1.508(9) . ?
C9 C25 1.546(8) . ?
C9 H9 0.9800 . ?
C10 C15 1.390(9) . ?
C10 C11 1.395(10) . ?
C11 C12 1.350(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(10) . ?
C14 C15 1.377(10) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.478(9) . ?
C16 N2 1.496(8) . ?
C16 H16 0.9800 . ?
C17 C22 1.403(10) . ?
C17 C18 1.409(11) . ?
C18 C19 1.353(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.523(11) . ?
C23 C29 1.507(10) . ?
C23 C24 1.515(10) . ?
C23 H23 0.9800 . ?
C24 N2 1.421(8) . ?
C24 O4 1.487(8) . ?
C24 H24 0.9800 . ?
C25 N2 1.448(8) . ?
C25 C26 1.516(10) . ?
C25 H25 0.9800 . ?
C26 O2 1.179(9) . ?
C26 O3 1.343(9) . ?
C27 O3 1.475(9) . ?
C27 C28 1.491(15) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.298(9) . ?
C29 C30 1.467(11) . ?
C30 C35 1.384(12) . ?
C30 C31 1.387(13) . ?
C31 C32 1.386(13) . ?
C31 H31 0.9300 . ?
C32 C33 1.341(17) . ?
C32 H32 0.9300 . ?
C33 C34 1.388(18) . ?
C33 H33 0.9300 . ?
C34 C35 1.374(15) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N1 H1 0.8600 . ?
N3 O4 1.400(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 N1 110.9(5) . . ?
C6 C1 C2 122.4(7) . . ?
N1 C1 C2 126.7(7) . . ?
C3 C2 C1 116.0(7) . . ?
C3 C2 H2 122.0 . . ?
C1 C2 H2 122.0 . . ?
C2 C3 C4 122.9(7) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.8(7) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.1(6) . . ?
C5 C6 C7 133.8(6) . . ?
C1 C6 C7 107.1(6) . . ?
C6 C7 C8 103.7(5) . . ?
C6 C7 C9 116.6(5) . . ?
C8 C7 C9 109.0(5) . . ?
C6 C7 C16 114.2(5) . . ?
C8 C7 C16 111.8(5) . . ?
C9 C7 C16 101.7(5) . . ?
O1 C8 N1 125.0(6) . . ?
O1 C8 C7 128.0(6) . . ?
N1 C8 C7 107.0(6) . . ?
C10 C9 C25 114.8(5) . . ?
C10 C9 C7 113.6(5) . . ?
C25 C9 C7 101.3(5) . . ?
C10 C9 H9 108.9 . . ?
C25 C9 H9 108.9 . . ?
C7 C9 H9 108.9 . . ?
C15 C10 C11 116.2(6) . . ?
C15 C10 C9 123.8(6) . . ?
C11 C10 C9 120.1(6) . . ?
C12 C11 C10 122.8(6) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C13 119.3(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.1(6) . . ?
C14 C13 Br1 120.7(5) . . ?
C12 C13 Br1 119.1(6) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 121.7(6) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C17 C16 N2 115.6(5) . . ?
C17 C16 C7 115.2(5) . . ?
N2 C16 C7 103.7(5) . . ?
C17 C16 H16 107.3 . . ?
N2 C16 H16 107.3 . . ?
C7 C16 H16 107.3 . . ?
C22 C17 C18 118.2(7) . . ?
C22 C17 C16 124.0(6) . . ?
C18 C17 C16 117.8(7) . . ?
C19 C18 C17 120.7(9) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.9(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.6(9) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.2(9) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.3(8) . . ?
C21 C22 C23 120.3(7) . . ?
C17 C22 C23 119.4(7) . . ?
C29 C23 C24 98.6(5) . . ?
C29 C23 C22 111.9(6) . . ?
C24 C23 C22 111.9(6) . . ?
C29 C23 H23 111.3 . . ?
C24 C23 H23 111.3 . . ?
C22 C23 H23 111.3 . . ?
N2 C24 O4 108.7(5) . . ?
N2 C24 C23 121.2(5) . . ?
O4 C24 C23 101.4(5) . . ?
N2 C24 H24 108.3 . . ?
O4 C24 H24 108.3 . . ?
C23 C24 H24 108.3 . . ?
N2 C25 C26 117.1(5) . . ?
N2 C25 C9 106.2(5) . . ?
C26 C25 C9 112.7(5) . . ?
N2 C25 H25 106.8 . . ?
C26 C25 H25 106.8 . . ?
C9 C25 H25 106.8 . . ?
O2 C26 O3 125.2(7) . . ?
O2 C26 C25 122.0(7) . . ?
O3 C26 C25 112.7(6) . . ?
O3 C27 C28 108.3(8) . . ?
O3 C27 H27A 110.0 . . ?
C28 C27 H27A 110.0 . . ?
O3 C27 H27B 110.0 . . ?
C28 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C30 120.3(7) . . ?
N3 C29 C23 112.0(6) . . ?
C30 C29 C23 127.7(7) . . ?
C35 C30 C31 118.6(8) . . ?
C35 C30 C29 120.4(9) . . ?
C31 C30 C29 120.9(8) . . ?
C32 C31 C30 119.4(10) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C33 C32 C31 122.1(13) . . ?
C33 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C32 C33 C34 119.0(11) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C35 C34 C33 120.2(12) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C30 120.8(12) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
C8 N1 C1 111.3(6) . . ?
C8 N1 H1 124.2 . . ?
C1 N1 H1 124.4 . . ?
C24 N2 C25 115.9(5) . . ?
C24 N2 C16 118.9(5) . . ?
C25 N2 C16 110.8(5) . . ?
C29 N3 O4 109.1(6) . . ?
C26 O3 C27 114.4(6) . . ?
N3 O4 C24 106.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.0(11) . . . . ?
N1 C1 C2 C3 -177.7(7) . . . . ?
C1 C2 C3 C4 0.8(13) . . . . ?
C2 C3 C4 C5 -3.9(13) . . . . ?
C3 C4 C5 C6 4.1(12) . . . . ?
C4 C5 C6 C1 -1.4(11) . . . . ?
C4 C5 C6 C7 177.8(7) . . . . ?
N1 C1 C6 C5 178.0(6) . . . . ?
C2 C1 C6 C5 -1.7(11) . . . . ?
N1 C1 C6 C7 -1.4(8) . . . . ?
C2 C1 C6 C7 178.9(7) . . . . ?
C5 C6 C7 C8 -177.7(8) . . . . ?
C1 C6 C7 C8 1.6(7) . . . . ?
C5 C6 C7 C9 62.5(10) . . . . ?
C1 C6 C7 C9 -118.2(6) . . . . ?
C5 C6 C7 C16 -55.7(10) . . . . ?
C1 C6 C7 C16 123.6(6) . . . . ?
C6 C7 C8 O1 179.5(7) . . . . ?
C9 C7 C8 O1 -55.7(9) . . . . ?
C16 C7 C8 O1 56.0(10) . . . . ?
C6 C7 C8 N1 -1.3(7) . . . . ?
C9 C7 C8 N1 123.5(6) . . . . ?
C16 C7 C8 N1 -124.8(6) . . . . ?
C6 C7 C9 C10 -41.0(7) . . . . ?
C8 C7 C9 C10 -157.9(5) . . . . ?
C16 C7 C9 C10 83.8(6) . . . . ?
C6 C7 C9 C25 -164.6(5) . . . . ?
C8 C7 C9 C25 78.4(6) . . . . ?
C16 C7 C9 C25 -39.8(6) . . . . ?
C25 C9 C10 C15 36.1(9) . . . . ?
C7 C9 C10 C15 -79.8(8) . . . . ?
C25 C9 C10 C11 -144.2(6) . . . . ?
C7 C9 C10 C11 99.9(7) . . . . ?
C15 C10 C11 C12 1.0(10) . . . . ?
C9 C10 C11 C12 -178.7(7) . . . . ?
C10 C11 C12 C13 0.7(11) . . . . ?
C11 C12 C13 C14 -1.7(11) . . . . ?
C11 C12 C13 Br1 -178.9(6) . . . . ?
C12 C13 C14 C15 0.8(11) . . . . ?
Br1 C13 C14 C15 178.1(5) . . . . ?
C13 C14 C15 C10 1.0(10) . . . . ?
C11 C10 C15 C14 -1.8(10) . . . . ?
C9 C10 C15 C14 177.9(6) . . . . ?
C6 C7 C16 C17 -73.7(8) . . . . ?
C8 C7 C16 C17 43.6(8) . . . . ?
C9 C7 C16 C17 159.8(6) . . . . ?
C6 C7 C16 N2 158.9(5) . . . . ?
C8 C7 C16 N2 -83.7(6) . . . . ?
C9 C7 C16 N2 32.5(6) . . . . ?
N2 C16 C17 C22 14.9(10) . . . . ?
C7 C16 C17 C22 -106.1(8) . . . . ?
N2 C16 C17 C18 -163.8(6) . . . . ?
C7 C16 C17 C18 75.1(9) . . . . ?
C22 C17 C18 C19 3.2(14) . . . . ?
C16 C17 C18 C19 -178.0(10) . . . . ?
C17 C18 C19 C20 -1(2) . . . . ?
C18 C19 C20 C21 -3(3) . . . . ?
C19 C20 C21 C22 3(2) . . . . ?
C20 C21 C22 C17 0.1(18) . . . . ?
C20 C21 C22 C23 -179.4(12) . . . . ?
C18 C17 C22 C21 -3.0(13) . . . . ?
C16 C17 C22 C21 178.2(9) . . . . ?
C18 C17 C22 C23 176.4(7) . . . . ?
C16 C17 C22 C23 -2.3(11) . . . . ?
C21 C22 C23 C29 48.4(11) . . . . ?
C17 C22 C23 C29 -131.0(8) . . . . ?
C21 C22 C23 C24 158.0(9) . . . . ?
C17 C22 C23 C24 -21.4(10) . . . . ?
C29 C23 C24 N2 153.0(6) . . . . ?
C22 C23 C24 N2 35.1(9) . . . . ?
C29 C23 C24 O4 32.7(6) . . . . ?
C22 C23 C24 O4 -85.1(6) . . . . ?
C10 C9 C25 N2 -89.5(6) . . . . ?
C7 C9 C25 N2 33.4(6) . . . . ?
C10 C9 C25 C26 40.0(8) . . . . ?
C7 C9 C25 C26 162.8(5) . . . . ?
N2 C25 C26 O2 173.2(7) . . . . ?
C9 C25 C26 O2 49.6(9) . . . . ?
N2 C25 C26 O3 -9.3(8) . . . . ?
C9 C25 C26 O3 -132.9(6) . . . . ?
C24 C23 C29 N3 -23.8(8) . . . . ?
C22 C23 C29 N3 94.1(8) . . . . ?
C24 C23 C29 C30 155.7(7) . . . . ?
C22 C23 C29 C30 -86.4(9) . . . . ?
N3 C29 C30 C35 -17.4(11) . . . . ?
C23 C29 C30 C35 163.2(7) . . . . ?
N3 C29 C30 C31 158.0(8) . . . . ?
C23 C29 C30 C31 -21.5(12) . . . . ?
C35 C30 C31 C32 0.9(12) . . . . ?
C29 C30 C31 C32 -174.6(7) . . . . ?
C30 C31 C32 C33 -1.3(15) . . . . ?
C31 C32 C33 C34 0.8(17) . . . . ?
C32 C33 C34 C35 0.0(17) . . . . ?
C33 C34 C35 C30 -0.4(15) . . . . ?
C31 C30 C35 C34 -0.1(12) . . . . ?
C29 C30 C35 C34 175.4(8) . . . . ?
O1 C8 N1 C1 179.8(7) . . . . ?
C7 C8 N1 C1 0.6(8) . . . . ?
C6 C1 N1 C8 0.5(9) . . . . ?
C2 C1 N1 C8 -179.8(7) . . . . ?
O4 C24 N2 C25 -131.6(5) . . . . ?
C23 C24 N2 C25 111.8(7) . . . . ?
O4 C24 N2 C16 92.5(6) . . . . ?
C23 C24 N2 C16 -24.1(9) . . . . ?
C26 C25 N2 C24 80.5(7) . . . . ?
C9 C25 N2 C24 -152.7(5) . . . . ?
C26 C25 N2 C16 -140.2(6) . . . . ?
C9 C25 N2 C16 -13.3(6) . . . . ?
C17 C16 N2 C24 -1.6(8) . . . . ?
C7 C16 N2 C24 125.5(6) . . . . ?
C17 C16 N2 C25 -139.5(6) . . . . ?
C7 C16 N2 C25 -12.5(7) . . . . ?
C30 C29 N3 O4 -176.4(6) . . . . ?
C23 C29 N3 O4 3.2(9) . . . . ?
O2 C26 O3 C27 3.2(11) . . . . ?
C25 C26 O3 C27 -174.2(7) . . . . ?
C28 C27 O3 C26 -87.7(9) . . . . ?
C29 N3 O4 C24 19.8(8) . . . . ?
N2 C24 O4 N3 -162.5(5) . . . . ?
C23 C24 O4 N3 -33.8(6) . . . . ?

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
N1 H1 O4 0.86 2.18 2.948(7) 148.7 1_655

_refine_diff_density_max         0.838
_refine_diff_density_min         -1.385
_refine_diff_density_rms         0.132


####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1937486'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 N4 O3, C H2 Cl2 '
_chemical_formula_sum            'C36 H30 Cl2 N4 O3'
_chemical_formula_weight         637.54

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.917(3)
_cell_length_b                   17.270(5)
_cell_length_c                   15.382(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.563(9)
_cell_angle_gamma                90
_cell_volume                     3162.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8284
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.952
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31256
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.423
_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             5560
_reflns_number_gt                3559
_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)+(0.1130P)²+1.9287P] 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       0.0087(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5560
_refine_ls_number_parameters     413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2328
_refine_ls_wR_factor_gt          0.2138
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.0761(3) 0.2949(2) 0.4817(2) 0.0512(9) Uani 1 1 d . . . . .
C2 C 0.0753(4) 0.3099(3) 0.5685(2) 0.0697(11) Uani 1 1 d . . . . .
H2 H 0.0610 0.2708 0.6080 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0961(4) 0.3841(3) 0.5961(3) 0.0746(12) Uani 1 1 d . . . . .
H3 H 0.0977 0.3954 0.6553 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1148(3) 0.4421(2) 0.5373(3) 0.0654(10) Uani 1 1 d . . . . .
H4 H 0.1271 0.4924 0.5571 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1156(3) 0.4269(2) 0.4494(2) 0.0519(9) Uani 1 1 d . . . . .
H5 H 0.1282 0.4664 0.4099 0.062 Uiso 1 1 calc R U . . .
C6 C 0.0973(3) 0.35187(19) 0.4207(2) 0.0434(8) Uani 1 1 d . . . . .
C7 C 0.0929(3) 0.31571(17) 0.33240(19) 0.0421(8) Uani 1 1 d . . . . .
C8 C 0.0601(3) 0.2316(2) 0.3517(2) 0.0537(9) Uani 1 1 d . . . . .
C9 C 0.2034(3) 0.31192(19) 0.2814(2) 0.0507(9) Uani 1 1 d . . . . .
H9 H 0.1878 0.2744 0.2347 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3116(3) 0.2851(2) 0.3258(2) 0.0575(10) Uani 1 1 d . . . . .
C11 C 0.3568(3) 0.3196(2) 0.4000(3) 0.0640(10) Uani 1 1 d . . . . .
H11 H 0.3183 0.3593 0.4266 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4607(4) 0.2949(3) 0.4352(3) 0.0769(13) Uani 1 1 d . . . . .
C13 C 0.4538(6) 0.3871(4) 0.5512(5) 0.136(2) Uani 1 1 d . . . . .
H13A H 0.4425 0.4299 0.5119 0.204 Uiso 1 1 calc R U . . .
H13B H 0.4979 0.4037 0.6015 0.204 Uiso 1 1 calc R U . . .
H13C H 0.3824 0.3685 0.5688 0.204 Uiso 1 1 calc R U . . .
C14 C 0.5183(4) 0.2374(3) 0.3961(4) 0.0962(16) Uani 1 1 d . . . . .
H14 H 0.5877 0.2215 0.4197 0.115 Uiso 1 1 calc R U . . .
C15 C 0.4744(5) 0.2034(3) 0.3226(4) 0.1024(17) Uani 1 1 d . . . . .
H15 H 0.5143 0.1645 0.2958 0.123 Uiso 1 1 calc R U . . .
C16 C 0.3702(4) 0.2263(3) 0.2872(3) 0.0818(13) Uani 1 1 d . . . . .
H16 H 0.3400 0.2020 0.2375 0.098 Uiso 1 1 calc R U . . .
C17 C 0.0173(3) 0.35528(17) 0.26291(19) 0.0419(8) Uani 1 1 d . . . . .
H17 H 0.0057 0.3192 0.2142 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0948(3) 0.38818(18) 0.28406(19) 0.0414(8) Uani 1 1 d . . . . .
C19 C -0.1602(3) 0.3569(2) 0.3474(2) 0.0523(9) Uani 1 1 d . . . . .
H19 H -0.1323 0.3156 0.3806 0.063 Uiso 1 1 calc R U . . .
C20 C -0.2644(3) 0.3852(2) 0.3622(2) 0.0633(11) Uani 1 1 d . . . . .
H20 H -0.3071 0.3628 0.4046 0.076 Uiso 1 1 calc R U . . .
C21 C -0.3066(3) 0.4468(3) 0.3144(2) 0.0654(11) Uani 1 1 d . . . . .
H21 H -0.3775 0.4664 0.3246 0.079 Uiso 1 1 calc R U . . .
C22 C -0.2423(3) 0.4793(2) 0.2511(2) 0.0560(9) Uani 1 1 d . . . . .
H22 H -0.2703 0.5214 0.2192 0.067 Uiso 1 1 calc R U . . .
C23 C -0.1368(3) 0.45023(18) 0.23444(19) 0.0430(8) Uani 1 1 d . . . . .
C24 C -0.0696(3) 0.48640(17) 0.16266(19) 0.0415(8) Uani 1 1 d . . . . .
H24 H -0.0681 0.5428 0.1692 0.050 Uiso 1 1 calc R U . . .
C25 C 0.0487(3) 0.45582(18) 0.1578(2) 0.0457(8) Uani 1 1 d . . . . .
H25 H 0.0991 0.4984 0.1437 0.055 Uiso 1 1 calc R U . . .
C26 C 0.2067(3) 0.3919(2) 0.2351(2) 0.0503(9) Uani 1 1 d . . . . .
H26 H 0.2284 0.3842 0.1750 0.060 Uiso 1 1 calc R U . . .
C27 C 0.2821(3) 0.4491(2) 0.2772(3) 0.0591(10) Uani 1 1 d . . . . .
C28 C -0.1162(3) 0.46520(17) 0.07284(19) 0.0429(8) Uani 1 1 d . . . . .
C29 C -0.2186(3) 0.4960(2) 0.02927(19) 0.0471(8) Uani 1 1 d . . . . .
C30 C -0.2535(3) 0.5703(2) 0.0453(2) 0.0580(10) Uani 1 1 d . . . . .
H30 H -0.2165 0.5990 0.0890 0.070 Uiso 1 1 calc R U . . .
C31 C -0.3426(3) 0.6033(3) -0.0024(3) 0.0720(12) Uani 1 1 d . . . . .
H31 H -0.3626 0.6543 0.0088 0.086 Uiso 1 1 calc R U . . .
C32 C -0.4014(3) 0.5630(3) -0.0650(3) 0.0743(13) Uani 1 1 d . . . . .
C33 C -0.4976(4) 0.5996(4) -0.1168(3) 0.116(2) Uani 1 1 d . . . . .
H33A H -0.5498 0.6215 -0.0778 0.174 Uiso 1 1 calc R U . . .
H33B H -0.5350 0.5611 -0.1525 0.174 Uiso 1 1 calc R U . . .
H33C H -0.4695 0.6398 -0.1531 0.174 Uiso 1 1 calc R U . . .
C34 C -0.3687(4) 0.4882(3) -0.0799(3) 0.0810(14) Uani 1 1 d . . . . .
H34 H -0.4086 0.4593 -0.1220 0.097 Uiso 1 1 calc R U . . .
C35 C -0.2777(4) 0.4538(2) -0.0343(2) 0.0671(11) Uani 1 1 d . . . . .
H35 H -0.2571 0.4031 -0.0465 0.081 Uiso 1 1 calc R U . . .
C36 C 0.7829(11) 0.3304(6) 0.6412(9) 0.262(7) Uani 1 1 d . . . . .
H36A H 0.8479 0.3607 0.6261 0.315 Uiso 0.698(4) 1 calc R U P A 1
H36B H 0.7170 0.3584 0.6192 0.315 Uiso 0.698(4) 1 calc R U P A 1
H36C H 0.8541 0.3456 0.6693 0.315 Uiso 0.302(4) 1 calc R U P A 2
H36D H 0.7492 0.3729 0.6080 0.315 Uiso 0.302(4) 1 calc R U P A 2
Cl1 Cl 0.7881(2) 0.23932(14) 0.5814(2) 0.1893(11) Uani 1 1 d . . . . .
Cl2 Cl 0.7798(4) 0.3293(2) 0.7476(3) 0.1984(17) Uani 0.698(4) 1 d . . P A 1
Cl2' Cl 0.6972(10) 0.2872(6) 0.7059(7) 0.1984(17) Uani 0.302(4) 1 d . . P A 2
N1 N 0.0537(3) 0.22510(16) 0.43803(19) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.0375 0.1827 0.4639 0.073 Uiso 1 1 calc R U . . .
N2 N 0.0903(2) 0.41843(14) 0.23439(16) 0.0440(7) Uani 1 1 d . . . . .
N3 N 0.3405(3) 0.4937(2) 0.3085(3) 0.0888(12) Uani 1 1 d . . . . .
N4 N -0.0543(3) 0.41768(16) 0.03263(17) 0.0531(8) Uani 1 1 d . . . . .
O1 O 0.0472(3) 0.18045(14) 0.29858(17) 0.0751(9) Uani 1 1 d . . . . .
O2 O 0.5107(3) 0.3271(2) 0.5091(3) 0.1042(11) Uani 1 1 d . . . . .
O3 O 0.0420(2) 0.40038(14) 0.08491(15) 0.0582(7) 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 C2 1.361(5) . ?
C1 C6 1.389(5) . ?
C1 N1 1.400(4) . ?
C2 C3 1.369(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(4) . ?
C7 C17 1.528(5) . ?
C7 C8 1.536(5) . ?
C7 C9 1.564(4) . ?
C8 O1 1.208(4) . ?
C8 N1 1.339(4) . ?
C9 C10 1.505(5) . ?
C9 C26 1.555(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.375(5) . ?
C10 C16 1.383(5) . ?
C11 C12 1.396(6) . ?
C11 H11 0.9300 . ?
C12 C14 1.362(7) . ?
C12 O2 1.377(6) . ?
C13 O2 1.411(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.357(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N2 1.473(4) . ?
C17 C18 1.501(4) . ?
C17 H17 0.9800 . ?
C18 C19 1.384(4) . ?
C18 C23 1.396(5) . ?
C19 C20 1.364(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.527(4) . ?
C24 C25 1.510(5) . ?
C24 C28 1.511(4) . ?
C24 H24 0.9800 . ?
C25 N2 1.413(4) . ?
C25 O3 1.474(4) . ?
C25 H25 0.9800 . ?
C26 N2 1.462(4) . ?
C26 C27 1.466(6) . ?
C26 H26 0.9800 . ?
C27 N3 1.132(5) . ?
C28 N4 1.281(4) . ?
C28 C29 1.466(5) . ?
C29 C30 1.373(5) . ?
C29 C35 1.387(5) . ?
C30 C31 1.387(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.357(6) . ?
C31 H31 0.9300 . ?
C32 C34 1.371(7) . ?
C32 C33 1.507(6) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.397(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 Cl2' 1.638(15) . ?
C36 Cl2 1.639(13) . ?
C36 Cl1 1.825(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?
C36 H36D 0.9700 . ?
N1 H1 0.8600 . ?
N4 O3 1.403(4) . ?

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
C2 C1 C6 122.5(4) . . ?
C2 C1 N1 128.6(3) . . ?
C6 C1 N1 108.8(3) . . ?
C1 C2 C3 118.2(4) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 132.8(3) . . ?
C1 C6 C7 108.5(3) . . ?
C6 C7 C17 116.4(3) . . ?
C6 C7 C8 102.6(2) . . ?
C17 C7 C8 114.3(3) . . ?
C6 C7 C9 118.5(3) . . ?
C17 C7 C9 98.7(2) . . ?
C8 C7 C9 106.5(2) . . ?
O1 C8 N1 126.7(3) . . ?
O1 C8 C7 125.9(3) . . ?
N1 C8 C7 107.3(3) . . ?
C10 C9 C26 116.2(3) . . ?
C10 C9 C7 120.6(3) . . ?
C26 C9 C7 103.4(2) . . ?
C10 C9 H9 105.1 . . ?
C26 C9 H9 105.1 . . ?
C7 C9 H9 105.1 . . ?
C11 C10 C16 119.2(4) . . ?
C11 C10 C9 122.7(3) . . ?
C16 C10 C9 118.0(4) . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C14 C12 O2 116.8(5) . . ?
C14 C12 C11 120.5(5) . . ?
O2 C12 C11 122.7(4) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C12 C14 H14 120.0 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C10 C16 C15 119.9(5) . . ?
C10 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N2 C17 C18 109.1(2) . . ?
N2 C17 C7 101.7(2) . . ?
C18 C17 C7 121.3(2) . . ?
N2 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
C7 C17 H17 108.0 . . ?
C19 C18 C23 119.0(3) . . ?
C19 C18 C17 122.6(3) . . ?
C23 C18 C17 118.3(3) . . ?
C20 C19 C18 121.5(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 119.3(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 121.1(4) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C18 118.9(3) . . ?
C22 C23 C24 119.6(3) . . ?
C18 C23 C24 121.5(3) . . ?
C25 C24 C28 100.1(2) . . ?
C25 C24 C23 114.4(3) . . ?
C28 C24 C23 112.3(3) . . ?
C25 C24 H24 109.9 . . ?
C28 C24 H24 109.9 . . ?
C23 C24 H24 109.9 . . ?
N2 C25 O3 110.0(2) . . ?
N2 C25 C24 114.3(2) . . ?
O3 C25 C24 104.2(3) . . ?
N2 C25 H25 109.4 . . ?
O3 C25 H25 109.4 . . ?
C24 C25 H25 109.4 . . ?
N2 C26 C27 110.7(3) . . ?
N2 C26 C9 103.8(2) . . ?
C27 C26 C9 115.1(3) . . ?
N2 C26 H26 109.0 . . ?
C27 C26 H26 109.0 . . ?
C9 C26 H26 109.0 . . ?
N3 C27 C26 179.0(4) . . ?
N4 C28 C29 119.8(3) . . ?
N4 C28 C24 113.6(3) . . ?
C29 C28 C24 126.5(3) . . ?
C30 C29 C35 118.0(4) . . ?
C30 C29 C28 120.6(3) . . ?
C35 C29 C28 121.2(3) . . ?
C29 C30 C31 121.3(4) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C32 C31 C30 121.6(4) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C34 117.4(4) . . ?
C31 C32 C33 121.1(5) . . ?
C34 C32 C33 121.5(5) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 C35 122.4(4) . . ?
C32 C34 H34 118.8 . . ?
C35 C34 H34 118.8 . . ?
C29 C35 C34 119.3(4) . . ?
C29 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
Cl2' C36 Cl1 87.0(7) . . ?
Cl2 C36 Cl1 119.7(6) . . ?
Cl2 C36 H36A 107.4 . . ?
Cl1 C36 H36A 107.4 . . ?
Cl2 C36 H36B 107.4 . . ?
Cl1 C36 H36B 107.4 . . ?
H36A C36 H36B 106.9 . . ?
Cl2' C36 H36C 114.1 . . ?
Cl1 C36 H36C 114.1 . . ?
Cl2' C36 H36D 114.1 . . ?
Cl1 C36 H36D 114.1 . . ?
H36C C36 H36D 111.3 . . ?
C8 N1 C1 112.6(3) . . ?
C8 N1 H1 123.7 . . ?
C1 N1 H1 123.7 . . ?
C25 N2 C26 116.5(2) . . ?
C25 N2 C17 113.4(3) . . ?
C26 N2 C17 109.8(2) . . ?
C28 N4 O3 109.5(3) . . ?
C12 O2 C13 118.5(4) . . ?
N4 O3 C25 108.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(6) . . . . ?
N1 C1 C2 C3 -177.6(4) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
N1 C1 C6 C5 176.5(3) . . . . ?
C2 C1 C6 C7 179.5(3) . . . . ?
N1 C1 C6 C7 -2.4(4) . . . . ?
C5 C6 C7 C17 -50.3(5) . . . . ?
C1 C6 C7 C17 128.5(3) . . . . ?
C5 C6 C7 C8 -175.9(4) . . . . ?
C1 C6 C7 C8 2.9(3) . . . . ?
C5 C6 C7 C9 67.2(5) . . . . ?
C1 C6 C7 C9 -114.1(3) . . . . ?
C6 C7 C8 O1 -179.6(4) . . . . ?
C17 C7 C8 O1 53.4(5) . . . . ?
C9 C7 C8 O1 -54.5(5) . . . . ?
C6 C7 C8 N1 -2.3(4) . . . . ?
C17 C7 C8 N1 -129.3(3) . . . . ?
C9 C7 C8 N1 122.9(3) . . . . ?
C6 C7 C9 C10 46.4(4) . . . . ?
C17 C7 C9 C10 172.9(3) . . . . ?
C8 C7 C9 C10 -68.5(4) . . . . ?
C6 C7 C9 C26 -85.6(3) . . . . ?
C17 C7 C9 C26 40.9(3) . . . . ?
C8 C7 C9 C26 159.6(3) . . . . ?
C26 C9 C10 C11 69.9(4) . . . . ?
C7 C9 C10 C11 -56.4(5) . . . . ?
C26 C9 C10 C16 -106.5(4) . . . . ?
C7 C9 C10 C16 127.3(4) . . . . ?
C16 C10 C11 C12 0.0(6) . . . . ?
C9 C10 C11 C12 -176.3(3) . . . . ?
C10 C11 C12 C14 0.8(6) . . . . ?
C10 C11 C12 O2 179.8(4) . . . . ?
O2 C12 C14 C15 -179.6(5) . . . . ?
C11 C12 C14 C15 -0.5(7) . . . . ?
C12 C14 C15 C16 -0.6(8) . . . . ?
C11 C10 C16 C15 -1.0(6) . . . . ?
C9 C10 C16 C15 175.5(4) . . . . ?
C14 C15 C16 C10 1.3(8) . . . . ?
C6 C7 C17 N2 81.7(3) . . . . ?
C8 C7 C17 N2 -158.8(2) . . . . ?
C9 C7 C17 N2 -46.2(3) . . . . ?
C6 C7 C17 C18 -39.4(4) . . . . ?
C8 C7 C17 C18 80.1(3) . . . . ?
C9 C7 C17 C18 -167.3(3) . . . . ?
N2 C17 C18 C19 -148.8(3) . . . . ?
C7 C17 C18 C19 -31.3(4) . . . . ?
N2 C17 C18 C23 34.8(4) . . . . ?
C7 C17 C18 C23 152.3(3) . . . . ?
C23 C18 C19 C20 0.1(5) . . . . ?
C17 C18 C19 C20 -176.4(3) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C21 C22 C23 C18 -1.4(5) . . . . ?
C21 C22 C23 C24 178.5(3) . . . . ?
C19 C18 C23 C22 1.0(4) . . . . ?
C17 C18 C23 C22 177.6(3) . . . . ?
C19 C18 C23 C24 -179.0(3) . . . . ?
C17 C18 C23 C24 -2.4(4) . . . . ?
C22 C23 C24 C25 173.3(3) . . . . ?
C18 C23 C24 C25 -6.7(4) . . . . ?
C22 C23 C24 C28 -73.4(4) . . . . ?
C18 C23 C24 C28 106.5(3) . . . . ?
C28 C24 C25 N2 -139.3(3) . . . . ?
C23 C24 C25 N2 -19.0(4) . . . . ?
C28 C24 C25 O3 -19.1(3) . . . . ?
C23 C24 C25 O3 101.1(3) . . . . ?
C10 C9 C26 N2 -154.9(3) . . . . ?
C7 C9 C26 N2 -20.4(3) . . . . ?
C10 C9 C26 C27 -33.7(4) . . . . ?
C7 C9 C26 C27 100.8(3) . . . . ?
C25 C24 C28 N4 13.5(3) . . . . ?
C23 C24 C28 N4 -108.4(3) . . . . ?
C25 C24 C28 C29 -163.7(3) . . . . ?
C23 C24 C28 C29 74.4(4) . . . . ?
N4 C28 C29 C30 -145.7(3) . . . . ?
C24 C28 C29 C30 31.4(5) . . . . ?
N4 C28 C29 C35 28.9(4) . . . . ?
C24 C28 C29 C35 -154.1(3) . . . . ?
C35 C29 C30 C31 -2.1(5) . . . . ?
C28 C29 C30 C31 172.6(3) . . . . ?
C29 C30 C31 C32 2.0(6) . . . . ?
C30 C31 C32 C34 -0.5(6) . . . . ?
C30 C31 C32 C33 -179.6(4) . . . . ?
C31 C32 C34 C35 -1.0(6) . . . . ?
C33 C32 C34 C35 178.2(4) . . . . ?
C30 C29 C35 C34 0.7(5) . . . . ?
C28 C29 C35 C34 -174.0(3) . . . . ?
C32 C34 C35 C29 0.8(6) . . . . ?
O1 C8 N1 C1 178.3(4) . . . . ?
C7 C8 N1 C1 1.0(4) . . . . ?
C2 C1 N1 C8 178.8(4) . . . . ?
C6 C1 N1 C8 0.9(4) . . . . ?
O3 C25 N2 C26 66.7(3) . . . . ?
C24 C25 N2 C26 -176.4(3) . . . . ?
O3 C25 N2 C17 -62.1(3) . . . . ?
C24 C25 N2 C17 54.7(3) . . . . ?
C27 C26 N2 C25 95.9(3) . . . . ?
C9 C26 N2 C25 -140.0(3) . . . . ?
C27 C26 N2 C17 -133.5(3) . . . . ?
C9 C26 N2 C17 -9.4(3) . . . . ?
C18 C17 N2 C25 -62.2(3) . . . . ?
C7 C17 N2 C25 168.5(2) . . . . ?
C18 C17 N2 C26 165.5(3) . . . . ?
C7 C17 N2 C26 36.2(3) . . . . ?
C29 C28 N4 O3 176.1(3) . . . . ?
C24 C28 N4 O3 -1.2(3) . . . . ?
C14 C12 O2 C13 179.7(5) . . . . ?
C11 C12 O2 C13 0.6(7) . . . . ?
C28 N4 O3 C25 -12.3(3) . . . . ?
N2 C25 O3 N4 143.2(2) . . . . ?
C24 C25 O3 N4 20.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N4 0.86 2.33 3.165(4) 164.6 4_566
N1 H1 O3 0.86 2.35 3.138(4) 152.8 4_566

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.052

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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 1937490'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H29 N5 O2'
_chemical_formula_sum            'C36 H29 N5 O2'
_chemical_formula_weight         563.64

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                   7.7920(5)
_cell_length_b                   12.8131(8)
_cell_length_c                   14.7154(9)
_cell_angle_alpha                96.214(2)
_cell_angle_beta                 96.001(2)
_cell_angle_gamma                98.326(2)
_cell_volume                     1434.32(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5936
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.78

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             592
_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    0.083
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20659
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5621
_reflns_number_gt                3514
_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)+(0.0589P)²+0.2420P] 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         5621
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.3701(2) 0.26445(15) 0.55452(11) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.4885 0.2833 0.5383 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3137(2) 0.14640(14) 0.52752(12) 0.0317(4) Uani 1 1 d . . . . .
C3 C 0.3594(2) 0.07366(16) 0.58536(13) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.4268 0.0977 0.6417 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3055(3) -0.03462(16) 0.56021(14) 0.0452(5) Uani 1 1 d . . . . .
H4 H 0.3380 -0.0828 0.5992 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2042(3) -0.07043(17) 0.47769(14) 0.0457(5) Uani 1 1 d . . . . .
H5 H 0.1654 -0.1428 0.4612 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1601(3) 0.00126(17) 0.41936(13) 0.0427(5) Uani 1 1 d . . . . .
H6 H 0.0910 -0.0233 0.3636 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2172(2) 0.10971(16) 0.44259(12) 0.0356(5) Uani 1 1 d . . . . .
C8 C 0.1707(3) 0.18786(16) 0.37855(12) 0.0423(5) Uani 1 1 d . . . . .
H8 H 0.0639 0.1554 0.3382 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1396(3) 0.29301(17) 0.42621(13) 0.0476(5) Uani 1 1 d . . . . .
H9 H 0.0185 0.2881 0.4398 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2157(3) 0.41477(15) 0.56911(12) 0.0377(5) Uani 1 1 d . . . . .
H10 H 0.0976 0.3955 0.5856 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2287(3) 0.51778(18) 0.53144(13) 0.0440(5) Uani 1 1 d . . . . .
C12 C 0.3205(3) 0.2125(2) 0.94789(14) 0.0617(7) Uani 1 1 d . . . . .
H12 H 0.4386 0.2405 0.9531 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2459(4) 0.1843(3) 1.02446(17) 0.0877(9) Uani 1 1 d . . . . .
H13 H 0.3143 0.1939 1.0813 0.105 Uiso 1 1 calc R U . . .
C14 C 0.0741(5) 0.1427(3) 1.0180(2) 0.0882(9) Uani 1 1 d . . . . .
H14 H 0.0247 0.1243 1.0700 0.106 Uiso 1 1 calc R U . . .
C15 C -0.0263(4) 0.1282(2) 0.93364(18) 0.0762(8) Uani 1 1 d . . . . .
H15 H -0.1437 0.0988 0.9286 0.091 Uiso 1 1 calc R U . . .
C16 C 0.0455(3) 0.15676(18) 0.85652(15) 0.0545(6) Uani 1 1 d . . . . .
H16 H -0.0234 0.1475 0.7998 0.065 Uiso 1 1 calc R U . . .
C17 C 0.2199(3) 0.19909(15) 0.86397(12) 0.0387(5) Uani 1 1 d . . . . .
C18 C 0.2223(2) 0.25160(14) 0.70369(12) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.3713(2) 0.30459(14) 0.65772(11) 0.0305(4) Uani 1 1 d . . . . .
C20 C 0.5253(2) 0.29361(15) 0.72303(12) 0.0335(4) Uani 1 1 d . . . . .
C21 C 0.7112(2) 0.3271(2) 0.71104(15) 0.0536(6) Uani 1 1 d . . . . .
H21A H 0.7839 0.3225 0.7668 0.080 Uiso 1 1 calc R U . . .
H21B H 0.7275 0.3991 0.6971 0.080 Uiso 1 1 calc R U . . .
H21C H 0.7424 0.2814 0.6614 0.080 Uiso 1 1 calc R U . . .
C22 C 0.3488(2) 0.42384(14) 0.65504(12) 0.0342(4) Uani 1 1 d . . . . .
H22 H 0.4595 0.4625 0.6418 0.041 Uiso 1 1 calc R U . . .
C23 C 0.3026(2) 0.47904(14) 0.74283(12) 0.0353(5) Uani 1 1 d . . . . .
C24 C 0.1365(3) 0.49998(17) 0.75387(14) 0.0484(5) Uani 1 1 d . . . . .
H24 H 0.0485 0.4822 0.7045 0.058 Uiso 1 1 calc R U . . .
C25 C 0.0985(3) 0.54709(19) 0.83724(16) 0.0624(7) Uani 1 1 d . . . . .
H25 H -0.0140 0.5614 0.8425 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2252(4) 0.57313(18) 0.91265(15) 0.0594(6) Uani 1 1 d . . . . .
C27 C 0.1829(4) 0.6217(3) 1.00399(18) 0.1010(11) Uani 1 1 d . . . . .
H27A H 0.0591 0.6210 1.0012 0.151 Uiso 1 1 calc R U . . .
H27B H 0.2423 0.6937 1.0173 0.151 Uiso 1 1 calc R U . . .
H27C H 0.2204 0.5814 1.0515 0.151 Uiso 1 1 calc R U . . .
C28 C 0.3916(3) 0.55534(17) 0.90057(14) 0.0570(6) Uani 1 1 d . . . . .
H28 H 0.4799 0.5742 0.9497 0.068 Uiso 1 1 calc R U . . .
C29 C 0.4309(3) 0.51028(15) 0.81753(13) 0.0462(5) Uani 1 1 d . . . . .
H29 H 0.5453 0.5006 0.8114 0.055 Uiso 1 1 calc R U . . .
C30 C 0.3058(3) 0.23126(17) 0.31839(12) 0.0461(5) Uani 1 1 d . . . . .
C31 C 0.4282(3) 0.17391(17) 0.27112(13) 0.0453(5) Uani 1 1 d . . . . .
C32 C 0.5893(3) 0.22711(19) 0.25654(16) 0.0599(6) Uani 1 1 d . . . . .
H32 H 0.6219 0.2986 0.2795 0.072 Uiso 1 1 calc R U . . .
C33 C 0.7011(4) 0.1756(2) 0.20865(19) 0.0740(8) Uani 1 1 d . . . . .
H33 H 0.8083 0.2124 0.1990 0.089 Uiso 1 1 calc R U . . .
C34 C 0.6551(4) 0.0698(2) 0.17487(18) 0.0735(8) Uani 1 1 d . . . . .
H34 H 0.7308 0.0351 0.1423 0.088 Uiso 1 1 calc R U . . .
C35 C 0.4970(3) 0.01572(19) 0.18938(15) 0.0606(7) Uani 1 1 d . . . . .
H35 H 0.4661 -0.0559 0.1666 0.073 Uiso 1 1 calc R U . . .
C36 C 0.3834(3) 0.06658(17) 0.23748(13) 0.0507(6) Uani 1 1 d . . . . .
H36 H 0.2770 0.0291 0.2474 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2564(2) 0.32898(13) 0.50713(10) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.2351(3) 0.59876(16) 0.50621(14) 0.0638(6) Uani 1 1 d . . . . .
N3 N 0.48258(19) 0.25445(12) 0.79584(10) 0.0364(4) Uani 1 1 d . . . . .
N4 N 0.29877(19) 0.22937(12) 0.78610(10) 0.0338(4) Uani 1 1 d . . . . .
N5 N 0.2995(3) 0.32839(15) 0.30687(12) 0.0651(6) Uani 1 1 d . . . . .
O1 O 0.06699(16) 0.23648(10) 0.67596(9) 0.0404(3) Uani 1 1 d . . . . .
O2 O 0.1715(2) 0.36539(13) 0.35837(9) 0.0684(5) 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 1.471(2) . ?
C1 C2 1.510(3) . ?
C1 C19 1.548(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.386(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(3) . ?
C8 C9 1.514(3) . ?
C8 C30 1.527(3) . ?
C8 H8 0.9800 . ?
C9 N1 1.411(2) . ?
C9 O2 1.451(3) . ?
C9 H9 0.9800 . ?
C10 N1 1.444(2) . ?
C10 C11 1.480(3) . ?
C10 C22 1.532(2) . ?
C10 H10 0.9800 . ?
C11 N2 1.135(3) . ?
C12 C17 1.372(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 N4 1.420(2) . ?
C18 O1 1.216(2) . ?
C18 N4 1.371(2) . ?
C18 C19 1.518(3) . ?
C19 C20 1.490(2) . ?
C19 C22 1.567(2) . ?
C20 N3 1.286(2) . ?
C20 C21 1.484(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.507(2) . ?
C22 H22 0.9800 . ?
C23 C24 1.382(3) . ?
C23 C29 1.388(3) . ?
C24 C25 1.387(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9300 . ?
C26 C28 1.375(3) . ?
C26 C27 1.508(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.377(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N5 1.281(3) . ?
C30 C31 1.471(3) . ?
C31 C32 1.388(3) . ?
C31 C36 1.391(3) . ?
C32 C33 1.373(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.372(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N3 N4 1.410(2) . ?
N5 O2 1.418(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.16(15) . . ?
N1 C1 C19 103.53(13) . . ?
C2 C1 C19 115.59(14) . . ?
N1 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C19 C1 H1 108.1 . . ?
C7 C2 C3 119.25(18) . . ?
C7 C2 C1 119.47(16) . . ?
C3 C2 C1 121.27(16) . . ?
C2 C3 C4 120.79(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.80(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.02(19) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 119.31(18) . . ?
C2 C7 C8 119.62(17) . . ?
C6 C7 C8 121.04(17) . . ?
C7 C8 C9 114.56(16) . . ?
C7 C8 C30 118.87(16) . . ?
C9 C8 C30 98.09(17) . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C30 C8 H8 108.2 . . ?
N1 C9 O2 109.40(18) . . ?
N1 C9 C8 112.85(16) . . ?
O2 C9 C8 103.30(15) . . ?
N1 C9 H9 110.4 . . ?
O2 C9 H9 110.4 . . ?
C8 C9 H9 110.4 . . ?
N1 C10 C11 113.89(15) . . ?
N1 C10 C22 105.03(14) . . ?
C11 C10 C22 109.85(16) . . ?
N1 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C22 C10 H10 109.3 . . ?
N2 C11 C10 176.6(2) . . ?
C17 C12 C13 119.7(2) . . ?
C17 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C12 C17 C16 119.84(19) . . ?
C12 C17 N4 118.92(19) . . ?
C16 C17 N4 121.24(18) . . ?
O1 C18 N4 126.94(17) . . ?
O1 C18 C19 127.72(16) . . ?
N4 C18 C19 105.25(15) . . ?
C20 C19 C18 101.23(14) . . ?
C20 C19 C1 118.13(14) . . ?
C18 C19 C1 115.52(15) . . ?
C20 C19 C22 111.87(14) . . ?
C18 C19 C22 107.81(14) . . ?
C1 C19 C22 102.24(13) . . ?
N3 C20 C21 121.18(17) . . ?
N3 C20 C19 113.03(16) . . ?
C21 C20 C19 125.75(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 116.70(15) . . ?
C23 C22 C19 115.11(14) . . ?
C10 C22 C19 101.10(14) . . ?
C23 C22 H22 107.8 . . ?
C10 C22 H22 107.8 . . ?
C19 C22 H22 107.8 . . ?
C24 C23 C29 117.27(18) . . ?
C24 C23 C22 123.27(17) . . ?
C29 C23 C22 119.46(17) . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C28 C26 C25 117.5(2) . . ?
C28 C26 C27 121.4(2) . . ?
C25 C26 C27 121.1(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 121.7(2) . . ?
C26 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C23 121.2(2) . . ?
C28 C29 H29 119.4 . . ?
C23 C29 H29 119.4 . . ?
N5 C30 C31 119.46(19) . . ?
N5 C30 C8 112.48(18) . . ?
C31 C30 C8 127.97(18) . . ?
C32 C31 C36 118.6(2) . . ?
C32 C31 C30 120.3(2) . . ?
C36 C31 C30 121.1(2) . . ?
C33 C32 C31 120.9(2) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 120.2(2) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.7(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.6(2) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C9 N1 C10 117.66(15) . . ?
C9 N1 C1 125.34(16) . . ?
C10 N1 C1 112.00(14) . . ?
C20 N3 N4 107.64(14) . . ?
C18 N4 N3 112.47(14) . . ?
C18 N4 C17 129.37(16) . . ?
N3 N4 C17 117.60(15) . . ?
C30 N5 O2 108.83(18) . . ?
N5 O2 C9 106.85(14) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.042

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

data_2b
_database_code_depnum_ccdc_archive 'CCDC 1937488'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 Br N3 O4'
_chemical_formula_sum            'C35 H28 Br N3 O4'
_chemical_formula_weight         634.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   15.5530(9)
_cell_length_b                   8.7812(6)
_cell_length_c                   22.8541(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.8964(17)
_cell_angle_gamma                90
_cell_volume                     2986.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7330
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      23.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.421
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_T_max  0.753
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30428
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6858
_reflns_number_gt                3576
_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)+(0.0780P)²+3.0958P] 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       0.0045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6858
_refine_ls_number_parameters     390
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.053
_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
Br1 Br 1.36949(4) 0.42924(8) 0.17337(4) 0.1191(4) Uani 1 1 d . . . . .
C1 C 0.9913(2) 0.4915(4) 0.22140(16) 0.0426(8) Uani 1 1 d . . . . .
C2 C 1.0379(3) 0.5134(5) 0.28207(19) 0.0612(11) Uani 1 1 d . . . . .
H2 H 1.0655 0.6058 0.2960 0.073 Uiso 1 1 calc R U . . .
C3 C 1.0420(3) 0.3922(6) 0.32130(19) 0.0662(13) Uani 1 1 d . . . . .
H3 H 1.0736 0.4029 0.3624 0.079 Uiso 1 1 calc R U . . .
C4 C 1.0006(3) 0.2573(5) 0.30113(17) 0.0588(11) Uani 1 1 d . . . . .
H4 H 1.0015 0.1797 0.3290 0.071 Uiso 1 1 calc R U . . .
C5 C 0.9574(2) 0.2343(4) 0.23979(15) 0.0449(9) Uani 1 1 d . . . . .
H5 H 0.9311 0.1410 0.2259 0.054 Uiso 1 1 calc R U . . .
C6 C 0.9542(2) 0.3529(4) 0.19945(14) 0.0358(8) Uani 1 1 d . . . . .
C7 C 0.9140(2) 0.3647(4) 0.13118(14) 0.0382(8) Uani 1 1 d . . . . .
C8 C 0.9216(2) 0.5352(4) 0.12024(18) 0.0464(9) Uani 1 1 d . . . . .
C9 C 0.9655(2) 0.2780(4) 0.09183(15) 0.0414(8) Uani 1 1 d . . . . .
H9 H 0.9446 0.3242 0.0511 0.050 Uiso 1 1 calc R U . . .
C10 C 1.0660(2) 0.2988(4) 0.11128(16) 0.0436(8) Uani 1 1 d . . . . .
C11 C 1.1220(2) 0.2545(5) 0.16799(17) 0.0521(10) Uani 1 1 d . . . . .
H11 H 1.0982 0.1996 0.1945 0.063 Uiso 1 1 calc R U . . .
C12 C 1.2121(3) 0.2905(5) 0.18565(19) 0.0601(11) Uani 1 1 d . . . . .
H12 H 1.2488 0.2617 0.2239 0.072 Uiso 1 1 calc R U . . .
C13 C 1.2472(3) 0.3696(5) 0.1460(2) 0.0667(12) Uani 1 1 d . . . . .
C14 C 1.1952(3) 0.4085(5) 0.0893(2) 0.0756(14) Uani 1 1 d . . . . .
H14 H 1.2202 0.4590 0.0623 0.091 Uiso 1 1 calc R U . . .
C15 C 1.1049(3) 0.3724(5) 0.07190(19) 0.0602(11) Uani 1 1 d . . . . .
H15 H 1.0695 0.3981 0.0329 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8203(2) 0.2962(4) 0.10518(15) 0.0388(8) Uani 1 1 d . . . . .
H16 H 0.7933 0.3342 0.0636 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7547(2) 0.3140(4) 0.14184(15) 0.0417(8) Uani 1 1 d . . . . .
C18 C 0.7577(2) 0.4321(5) 0.18245(17) 0.0514(10) Uani 1 1 d . . . . .
H18 H 0.7988 0.5108 0.1856 0.062 Uiso 1 1 calc R U . . .
C19 C 0.6998(3) 0.4340(6) 0.21849(19) 0.0663(12) Uani 1 1 d . . . . .
H19 H 0.7018 0.5142 0.2454 0.080 Uiso 1 1 calc R U . . .
C20 C 0.6399(3) 0.3182(6) 0.2145(2) 0.0717(13) Uani 1 1 d . . . . .
H20 H 0.6022 0.3179 0.2395 0.086 Uiso 1 1 calc R U . . .
C21 C 0.6353(3) 0.2018(6) 0.17342(19) 0.0622(11) Uani 1 1 d . . . . .
H21 H 0.5945 0.1230 0.1711 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6903(2) 0.1997(4) 0.13545(15) 0.0459(9) Uani 1 1 d . . . . .
C23 C 0.6796(2) 0.0834(4) 0.08538(17) 0.0489(9) Uani 1 1 d . . . . .
H23 H 0.6498 -0.0077 0.0948 0.059 Uiso 1 1 calc R U . . .
C24 C 0.7682(2) 0.0384(5) 0.07190(16) 0.0512(10) Uani 1 1 d . . . . .
H24 H 0.7827 -0.0680 0.0837 0.061 Uiso 1 1 calc R U . . .
C25 C 0.9235(2) 0.1158(4) 0.08432(16) 0.0444(9) Uani 1 1 d . . . . .
H25 H 0.9058 0.0899 0.0407 0.053 Uiso 1 1 calc R U . . .
C26 C 0.9825(2) -0.0117(4) 0.1190(2) 0.0504(9) Uani 1 1 d . . . . .
C27 C 1.1088(3) -0.1634(6) 0.1221(3) 0.1018(10) Uani 1 1 d D U . . .
H27A H 1.0911 -0.2594 0.1010 0.122 Uiso 1 1 calc R U . . .
H27B H 1.1079 -0.1756 0.1641 0.122 Uiso 1 1 calc R U . . .
C28 C 1.1999(3) -0.1235(7) 0.1210(3) 0.1100(12) Uani 1 1 d D U . . .
H28A H 1.1982 -0.0891 0.0808 0.165 Uiso 1 1 calc R U . . .
H28B H 1.2380 -0.2114 0.1314 0.165 Uiso 1 1 calc R U . . .
H28C H 1.2231 -0.0438 0.1500 0.165 Uiso 1 1 calc R U . . .
C29 C 0.6268(2) 0.1467(5) 0.02366(17) 0.0520(10) Uani 1 1 d . . . . .
C30 C 0.5384(3) 0.2181(5) 0.00766(17) 0.0550(10) Uani 1 1 d . . . . .
C31 C 0.4760(3) 0.1796(5) 0.0373(2) 0.0651(12) Uani 1 1 d . . . . .
H31 H 0.4913 0.1113 0.0698 0.078 Uiso 1 1 calc R U . . .
C32 C 0.3899(3) 0.2424(6) 0.0190(3) 0.0838(15) Uani 1 1 d . . . . .
H32 H 0.3484 0.2168 0.0396 0.101 Uiso 1 1 calc R U . . .
C33 C 0.3662(4) 0.3421(7) -0.0293(3) 0.0941(19) Uani 1 1 d . . . . .
H33 H 0.3083 0.3819 -0.0422 0.113 Uiso 1 1 calc R U . . .
C34 C 0.4286(4) 0.3828(7) -0.0586(2) 0.0910(18) Uani 1 1 d . . . . .
H34 H 0.4129 0.4525 -0.0906 0.109 Uiso 1 1 calc R U . . .
C35 C 0.5138(3) 0.3220(6) -0.04131(19) 0.0744(13) Uani 1 1 d . . . . .
H35 H 0.5550 0.3494 -0.0619 0.089 Uiso 1 1 calc R U . . .
N1 N 0.9714(2) 0.5979(3) 0.17321(15) 0.0520(8) Uani 1 1 d . . . . .
H1 H 0.9889 0.6913 0.1770 0.062 Uiso 1 1 calc R U . . .
N2 N 0.84149(18) 0.1334(3) 0.10302(13) 0.0417(7) Uani 1 1 d . . . . .
N3 N 0.6668(2) 0.1297(5) -0.01783(15) 0.0665(10) Uani 1 1 d . . . . .
O1 O 0.8903(2) 0.6006(3) 0.07154(13) 0.0688(8) Uani 1 1 d . . . . .
O2 O 0.9740(2) -0.0759(3) 0.16340(15) 0.0637(8) Uani 1 1 d . . . . .
O3 O 1.0451(2) -0.0443(4) 0.0924(2) 0.0960(10) Uani 1 1 d . U . . .
O4 O 0.74845(19) 0.0534(4) 0.00578(12) 0.0725(9) 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
Br1 C13 1.896(4) . ?
C1 C6 1.378(5) . ?
C1 C2 1.379(5) . ?
C1 N1 1.409(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 C16 1.528(4) . ?
C7 C8 1.529(5) . ?
C7 C9 1.564(5) . ?
C8 O1 1.221(4) . ?
C8 N1 1.350(5) . ?
C9 C10 1.506(5) . ?
C9 C25 1.556(5) . ?
C9 H9 0.9800 . ?
C10 C15 1.382(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(7) . ?
C14 C15 1.381(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.471(4) . ?
C16 C17 1.505(5) . ?
C16 H16 0.9800 . ?
C17 C18 1.384(5) . ?
C17 C22 1.395(5) . ?
C18 C19 1.385(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.507(5) . ?
C23 C29 1.516(5) . ?
C23 C24 1.548(5) . ?
C23 H23 0.9800 . ?
C24 N2 1.424(4) . ?
C24 O4 1.458(5) . ?
C24 H24 0.9800 . ?
C25 N2 1.466(4) . ?
C25 C26 1.516(5) . ?
C25 H25 0.9800 . ?
C26 O2 1.202(5) . ?
C26 O3 1.320(5) . ?
C27 O3 1.464(6) . ?
C27 C28 1.467(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.285(5) . ?
C29 C30 1.458(5) . ?
C30 C31 1.379(6) . ?
C30 C35 1.408(6) . ?
C31 C32 1.395(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.376(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.376(7) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N1 H1 0.8600 . ?
N3 O4 1.397(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.1(4) . . ?
C6 C1 N1 109.2(3) . . ?
C2 C1 N1 128.7(4) . . ?
C1 C2 C3 117.2(4) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C7 108.7(3) . . ?
C5 C6 C7 131.8(3) . . ?
C6 C7 C16 115.9(3) . . ?
C6 C7 C8 102.0(3) . . ?
C16 C7 C8 115.6(3) . . ?
C6 C7 C9 115.8(3) . . ?
C16 C7 C9 100.1(3) . . ?
C8 C7 C9 107.8(3) . . ?
O1 C8 N1 126.7(4) . . ?
O1 C8 C7 125.5(4) . . ?
N1 C8 C7 107.7(3) . . ?
C10 C9 C25 120.6(3) . . ?
C10 C9 C7 115.6(3) . . ?
C25 C9 C7 103.9(3) . . ?
C10 C9 H9 105.1 . . ?
C25 C9 H9 105.1 . . ?
C7 C9 H9 105.1 . . ?
C15 C10 C11 117.6(3) . . ?
C15 C10 C9 118.5(3) . . ?
C11 C10 C9 123.8(3) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 Br1 120.5(3) . . ?
C12 C13 Br1 118.3(4) . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
N2 C16 C17 108.3(3) . . ?
N2 C16 C7 101.4(3) . . ?
C17 C16 C7 117.8(3) . . ?
N2 C16 H16 109.6 . . ?
C17 C16 H16 109.6 . . ?
C7 C16 H16 109.6 . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 C16 123.8(3) . . ?
C22 C17 C16 116.7(3) . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 121.2(4) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 118.7(4) . . ?
C21 C22 C23 122.2(3) . . ?
C17 C22 C23 119.0(3) . . ?
C22 C23 C29 111.6(3) . . ?
C22 C23 C24 114.6(3) . . ?
C29 C23 C24 100.4(3) . . ?
C22 C23 H23 109.9 . . ?
C29 C23 H23 109.9 . . ?
C24 C23 H23 109.9 . . ?
N2 C24 O4 111.2(3) . . ?
N2 C24 C23 112.4(3) . . ?
O4 C24 C23 104.6(3) . . ?
N2 C24 H24 109.5 . . ?
O4 C24 H24 109.5 . . ?
C23 C24 H24 109.5 . . ?
N2 C25 C26 111.8(3) . . ?
N2 C25 C9 104.1(3) . . ?
C26 C25 C9 116.6(3) . . ?
N2 C25 H25 108.0 . . ?
C26 C25 H25 108.0 . . ?
C9 C25 H25 108.0 . . ?
O2 C26 O3 124.3(4) . . ?
O2 C26 C25 126.1(4) . . ?
O3 C26 C25 109.6(4) . . ?
O3 C27 C28 110.4(4) . . ?
O3 C27 H27A 109.6 . . ?
C28 C27 H27A 109.6 . . ?
O3 C27 H27B 109.6 . . ?
C28 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C30 119.2(4) . . ?
N3 C29 C23 113.3(3) . . ?
C30 C29 C23 127.4(4) . . ?
C31 C30 C35 118.8(4) . . ?
C31 C30 C29 121.3(4) . . ?
C35 C30 C29 119.8(4) . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 120.2(5) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 119.6(5) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 121.1(5) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C30 119.8(5) . . ?
C34 C35 H35 120.1 . . ?
C30 C35 H35 120.1 . . ?
C8 N1 C1 111.6(3) . . ?
C8 N1 H1 124.2 . . ?
C1 N1 H1 124.2 . . ?
C24 N2 C25 115.5(3) . . ?
C24 N2 C16 115.6(3) . . ?
C25 N2 C16 109.5(3) . . ?
C29 N3 O4 110.6(3) . . ?
C26 O3 C27 115.6(4) . . ?
N3 O4 C24 109.8(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.07 2.874(4) 155.2 1_565

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_3l
_database_code_depnum_ccdc_archive 'CCDC 1937507'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 Cl N5 O2'
_chemical_formula_sum            'C36 H28 Cl N5 O2'
_chemical_formula_weight         598.08

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                   7.9066(7)
_cell_length_b                   12.8759(12)
_cell_length_c                   15.1112(12)
_cell_angle_alpha                93.932(3)
_cell_angle_beta                 100.459(3)
_cell_angle_gamma                98.838(3)
_cell_volume                     1487.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4166
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      22.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_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          0.200
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21391
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         25.999
_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             5813
_reflns_number_gt                3043
_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)+(0.0576P)²+1.2023P] 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         5813
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1593
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.8554(4) 0.2638(2) 0.05909(19) 0.0352(8) Uani 1 1 d . . . . .
H1 H 0.9715 0.2856 0.0456 0.042 Uiso 1 1 calc R U . . .
C2 C 0.8035(4) 0.1468(2) 0.0317(2) 0.0346(8) Uani 1 1 d . . . . .
C3 C 0.8660(4) 0.0738(3) 0.0870(2) 0.0433(9) Uani 1 1 d . . . . .
H3 H 0.9380 0.0974 0.1429 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8232(5) -0.0330(3) 0.0606(2) 0.0480(9) Uani 1 1 d . . . . .
H4 H 0.8680 -0.0807 0.0980 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7147(5) -0.0692(3) -0.0209(2) 0.0478(9) Uani 1 1 d . . . . .
H5 H 0.6844 -0.1413 -0.0385 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6514(4) 0.0022(3) -0.0760(2) 0.0447(9) Uani 1 1 d . . . . .
H6 H 0.5765 -0.0222 -0.1308 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6969(4) 0.1101(3) -0.0515(2) 0.0374(8) Uani 1 1 d . . . . .
C8 C 0.6283(4) 0.1879(3) -0.1123(2) 0.0447(9) Uani 1 1 d . . . . .
H8 H 0.5172 0.1532 -0.1501 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5985(5) 0.2878(3) -0.0645(2) 0.0484(9) Uani 1 1 d . . . . .
H9 H 0.4857 0.2775 -0.0453 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7123(4) 0.4158(2) 0.06750(19) 0.0374(8) Uani 1 1 d . . . . .
H10 H 0.5946 0.4024 0.0808 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7380(5) 0.5167(3) 0.0276(2) 0.0459(9) Uani 1 1 d . . . . .
C12 C 0.8225(6) 0.2163(4) 0.4445(2) 0.0773(14) Uani 1 1 d . . . . .
H12 H 0.9419 0.2392 0.4511 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7514(8) 0.1960(5) 0.5194(3) 0.108(2) Uani 1 1 d . . . . .
H13 H 0.8229 0.2055 0.5764 0.130 Uiso 1 1 calc R U . . .
C14 C 0.5784(8) 0.1624(5) 0.5105(3) 0.1058(19) Uani 1 1 d . . . . .
H14 H 0.5309 0.1486 0.5613 0.127 Uiso 1 1 calc R U . . .
C15 C 0.4731(6) 0.1488(4) 0.4268(3) 0.0861(15) Uani 1 1 d . . . . .
H15 H 0.3539 0.1256 0.4210 0.103 Uiso 1 1 calc R U . . .
C16 C 0.5421(5) 0.1690(3) 0.3507(3) 0.0593(10) Uani 1 1 d . . . . .
H16 H 0.4703 0.1599 0.2937 0.071 Uiso 1 1 calc R U . . .
C17 C 0.7185(5) 0.2029(3) 0.3607(2) 0.0429(9) Uani 1 1 d . . . . .
C18 C 0.7167(4) 0.2490(2) 0.20087(19) 0.0308(7) Uani 1 1 d . . . . .
C19 C 0.8641(4) 0.3003(2) 0.15920(19) 0.0314(7) Uani 1 1 d . . . . .
C20 C 1.0188(4) 0.2870(2) 0.2267(2) 0.0359(8) Uani 1 1 d . . . . .
C21 C 1.2034(4) 0.3185(3) 0.2187(2) 0.0570(10) Uani 1 1 d . . . . .
H21A H 1.2781 0.3161 0.2759 0.085 Uiso 1 1 calc R U . . .
H21B H 1.2205 0.3889 0.2010 0.085 Uiso 1 1 calc R U . . .
H21C H 1.2311 0.2707 0.1739 0.085 Uiso 1 1 calc R U . . .
C22 C 0.8476(4) 0.4204(2) 0.15544(19) 0.0354(8) Uani 1 1 d . . . . .
H22 H 0.9590 0.4582 0.1456 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8084(4) 0.4731(2) 0.2399(2) 0.0344(8) Uani 1 1 d . . . . .
C24 C 0.9439(4) 0.5090(3) 0.3129(2) 0.0456(9) Uani 1 1 d . . . . .
H24 H 1.0580 0.5046 0.3075 0.055 Uiso 1 1 calc R U . . .
C25 C 0.9117(5) 0.5510(3) 0.3932(2) 0.0562(10) Uani 1 1 d . . . . .
H25 H 1.0045 0.5727 0.4416 0.067 Uiso 1 1 calc R U . . .
C26 C 0.7450(5) 0.5617(3) 0.4040(2) 0.0576(10) Uani 1 1 d . . . . .
C27 C 0.7104(7) 0.6080(4) 0.4926(3) 0.1045(18) Uani 1 1 d . . . . .
H27A H 0.5871 0.6054 0.4882 0.157 Uiso 1 1 calc R U . . .
H27B H 0.7685 0.6801 0.5052 0.157 Uiso 1 1 calc R U . . .
H27C H 0.7536 0.5680 0.5405 0.157 Uiso 1 1 calc R U . . .
C28 C 0.6130(5) 0.5297(3) 0.3305(2) 0.0586(10) Uani 1 1 d . . . . .
H28 H 0.4999 0.5379 0.3351 0.070 Uiso 1 1 calc R U . . .
C29 C 0.6423(4) 0.4857(3) 0.2498(2) 0.0477(9) Uani 1 1 d . . . . .
H29 H 0.5491 0.4644 0.2016 0.057 Uiso 1 1 calc R U . . .
C30 C 0.7432(5) 0.2386(3) -0.1734(2) 0.0482(9) Uani 1 1 d . . . . .
C31 C 0.8706(5) 0.1918(3) -0.2162(2) 0.0476(9) Uani 1 1 d . . . . .
C32 C 1.0302(6) 0.2526(3) -0.2182(3) 0.0586(11) Uani 1 1 d . . . . .
H32 H 1.0550 0.3222 -0.1921 0.070 Uiso 1 1 calc R U . . .
C33 C 1.1518(6) 0.2126(3) -0.2577(3) 0.0674(12) Uani 1 1 d . . . . .
H33 H 1.2578 0.2548 -0.2589 0.081 Uiso 1 1 calc R U . . .
C34 C 1.1169(6) 0.1103(4) -0.2954(3) 0.0653(11) Uani 1 1 d . . . . .
C35 C 0.9603(6) 0.0472(3) -0.2945(3) 0.0617(11) Uani 1 1 d . . . . .
H35 H 0.9376 -0.0224 -0.3204 0.074 Uiso 1 1 calc R U . . .
C36 C 0.8371(5) 0.0879(3) -0.2550(2) 0.0537(10) Uani 1 1 d . . . . .
H36 H 0.7310 0.0455 -0.2543 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 1.2734(2) 0.05985(12) -0.34239(12) 0.1179(6) Uani 1 1 d . . . . .
N1 N 0.7373(4) 0.3276(2) 0.00989(16) 0.0426(7) Uani 1 1 d . . . . .
N2 N 0.7568(4) 0.5962(3) -0.0005(2) 0.0679(10) Uani 1 1 d . . . . .
N3 N 0.9786(3) 0.2482(2) 0.29750(17) 0.0408(7) Uani 1 1 d . . . . .
N4 N 0.7946(3) 0.2258(2) 0.28439(16) 0.0360(6) Uani 1 1 d . . . . .
N5 N 0.7234(5) 0.3335(3) -0.18564(19) 0.0669(10) Uani 1 1 d . . . . .
O1 O 0.5609(3) 0.23550(17) 0.16978(14) 0.0411(6) Uani 1 1 d . . . . .
O2 O 0.6016(4) 0.3609(2) -0.13268(16) 0.0669(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 1.472(4) . ?
C1 C2 1.506(4) . ?
C1 C19 1.539(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.388(4) . ?
C2 C7 1.389(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.500(4) . ?
C8 C9 1.503(5) . ?
C8 C30 1.520(5) . ?
C8 H8 0.9800 . ?
C9 N1 1.425(4) . ?
C9 O2 1.444(4) . ?
C9 H9 0.9800 . ?
C10 N1 1.443(4) . ?
C10 C11 1.471(5) . ?
C10 C22 1.538(4) . ?
C10 H10 0.9800 . ?
C11 N2 1.134(4) . ?
C12 C17 1.364(5) . ?
C12 C13 1.375(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.349(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 N4 1.421(4) . ?
C18 O1 1.217(3) . ?
C18 N4 1.373(4) . ?
C18 C19 1.510(4) . ?
C19 C20 1.484(4) . ?
C19 C22 1.576(4) . ?
C20 N3 1.282(4) . ?
C20 C21 1.483(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.508(4) . ?
C22 H22 0.9800 . ?
C23 C29 1.381(4) . ?
C23 C24 1.388(4) . ?
C24 C25 1.376(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(5) . ?
C25 H25 0.9300 . ?
C26 C28 1.370(5) . ?
C26 C27 1.515(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.382(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N5 1.278(4) . ?
C30 C31 1.470(5) . ?
C31 C32 1.386(5) . ?
C31 C36 1.390(5) . ?
C32 C33 1.365(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(5) . ?
C34 Cl1 1.721(4) . ?
C35 C36 1.381(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N3 N4 1.414(3) . ?
N5 O2 1.427(4) . ?

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 C2 113.7(2) . . ?
N1 C1 C19 103.7(2) . . ?
C2 C1 C19 116.4(2) . . ?
N1 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C19 C1 H1 107.5 . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 120.2(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 C8 121.1(3) . . ?
C2 C7 C8 119.4(3) . . ?
C7 C8 C9 115.2(3) . . ?
C7 C8 C30 118.5(3) . . ?
C9 C8 C30 97.7(3) . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C30 C8 H8 108.2 . . ?
N1 C9 O2 108.3(3) . . ?
N1 C9 C8 111.8(3) . . ?
O2 C9 C8 103.0(3) . . ?
N1 C9 H9 111.2 . . ?
O2 C9 H9 111.2 . . ?
C8 C9 H9 111.2 . . ?
N1 C10 C11 113.0(3) . . ?
N1 C10 C22 105.7(2) . . ?
C11 C10 C22 109.9(3) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C22 C10 H10 109.4 . . ?
N2 C11 C10 177.7(4) . . ?
C17 C12 C13 120.2(4) . . ?
C17 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C12 C17 C16 120.0(3) . . ?
C12 C17 N4 119.2(3) . . ?
C16 C17 N4 120.7(3) . . ?
O1 C18 N4 126.7(3) . . ?
O1 C18 C19 127.8(3) . . ?
N4 C18 C19 105.4(2) . . ?
C20 C19 C18 101.5(2) . . ?
C20 C19 C1 118.7(2) . . ?
C18 C19 C1 115.8(2) . . ?
C20 C19 C22 111.3(2) . . ?
C18 C19 C22 107.4(2) . . ?
C1 C19 C22 102.0(2) . . ?
N3 C20 C21 121.4(3) . . ?
N3 C20 C19 113.0(3) . . ?
C21 C20 C19 125.6(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 117.1(3) . . ?
C23 C22 C19 114.8(2) . . ?
C10 C22 C19 101.3(2) . . ?
C23 C22 H22 107.7 . . ?
C10 C22 H22 107.7 . . ?
C19 C22 H22 107.7 . . ?
C29 C23 C24 117.5(3) . . ?
C29 C23 C22 123.3(3) . . ?
C24 C23 C22 119.2(3) . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 121.8(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C28 C26 C25 116.9(3) . . ?
C28 C26 C27 121.5(4) . . ?
C25 C26 C27 121.6(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 122.1(4) . . ?
C26 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C23 C29 C28 120.8(3) . . ?
C23 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
N5 C30 C31 119.2(3) . . ?
N5 C30 C8 113.1(3) . . ?
C31 C30 C8 127.7(3) . . ?
C32 C31 C36 118.2(4) . . ?
C32 C31 C30 119.4(3) . . ?
C36 C31 C30 122.3(4) . . ?
C33 C32 C31 121.4(4) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C33 C32 119.6(4) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.9(4) . . ?
C33 C34 Cl1 119.2(4) . . ?
C35 C34 Cl1 120.0(3) . . ?
C34 C35 C36 119.5(4) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 120.4(4) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C9 N1 C10 116.5(3) . . ?
C9 N1 C1 124.9(3) . . ?
C10 N1 C1 111.8(2) . . ?
C20 N3 N4 107.8(2) . . ?
C18 N4 N3 111.9(2) . . ?
C18 N4 C17 129.1(3) . . ?
N3 N4 C17 117.9(2) . . ?
C30 N5 O2 107.6(3) . . ?
N5 O2 C9 106.6(2) . . ?

_refine_diff_density_max         0.749
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 1937491'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H31 N5 O3'
_chemical_formula_sum            'C37 H31 N5 O3'
_chemical_formula_weight         593.67

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.932(2)
_cell_length_b                   7.8696(17)
_cell_length_c                   16.941(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.606(7)
_cell_angle_gamma                90
_cell_volume                     1524.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      22.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_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          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12951
_diffrn_reflns_av_unetI/netI     0.1374
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             5536
_reflns_number_gt                3213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    0.852

_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)+(0.1622P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 967 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5536
_refine_ls_number_parameters     409
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2581
_refine_ls_wR_factor_gt          0.2124
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 0.8518(6) 0.6947(9) 0.1094(4) 0.0293(16) Uani 1 1 d . . . . .
H1 H 0.8542 0.7846 0.0698 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7247(6) 0.6407(9) 0.0991(4) 0.0350(17) Uani 1 1 d . . . . .
C3 C 0.6622(7) 0.6931(10) 0.1506(5) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.6933 0.7747 0.1905 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5516(8) 0.6250(12) 0.1437(6) 0.052(2) Uani 1 1 d . . . . .
H4 H 0.5089 0.6605 0.1788 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5074(8) 0.5059(12) 0.0848(6) 0.055(2) Uani 1 1 d . . . . .
H5 H 0.4338 0.4600 0.0798 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5689(7) 0.4528(11) 0.0332(6) 0.050(2) Uani 1 1 d . . . . .
H6 H 0.5381 0.3684 -0.0053 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6785(6) 0.5235(9) 0.0370(5) 0.0359(18) Uani 1 1 d . . . . .
C8 C 0.7452(6) 0.4699(10) -0.0226(5) 0.042(2) Uani 1 1 d . . . . .
H8 H 0.7180 0.3570 -0.0441 0.050 Uiso 1 1 calc R U . . .
C9 C 0.8798(6) 0.4630(10) 0.0171(4) 0.0375(18) Uani 1 1 d . . . . .
H9 H 0.9057 0.3443 0.0233 0.045 Uiso 1 1 calc R U . . .
C10 C 1.0387(6) 0.5503(9) 0.1401(4) 0.0338(17) Uani 1 1 d . . . . .
H10 H 1.0562 0.4560 0.1796 0.041 Uiso 1 1 calc R U . . .
C11 C 1.1219(7) 0.5478(10) 0.0921(5) 0.0392(18) Uani 1 1 d . . . . .
C12 C 0.9462(7) 0.8189(11) 0.4701(5) 0.049(2) Uani 1 1 d . . . . .
H12 H 1.0015 0.8972 0.4640 0.059 Uiso 1 1 calc R U . . .
C13 C 0.9301(8) 0.7898(12) 0.5463(5) 0.053(2) Uani 1 1 d . . . . .
H13 H 0.9755 0.8495 0.5916 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8502(9) 0.6768(12) 0.5573(5) 0.056(2) Uani 1 1 d . . . . .
H14 H 0.8409 0.6593 0.6093 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7828(8) 0.5884(12) 0.4903(5) 0.056(2) Uani 1 1 d . . . . .
H15 H 0.7282 0.5099 0.4972 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7960(7) 0.6155(10) 0.4128(5) 0.044(2) Uani 1 1 d . . . . .
H16 H 0.7492 0.5571 0.3676 0.052 Uiso 1 1 calc R U . . .
C17 C 0.8786(6) 0.7296(9) 0.4027(4) 0.0312(16) Uani 1 1 d . . . . .
C18 C 0.9048(6) 0.6446(9) 0.2665(4) 0.0313(17) Uani 1 1 d . . . . .
C19 C 0.9243(6) 0.7479(9) 0.1970(4) 0.0305(16) Uani 1 1 d . . . . .
C20 C 0.9088(7) 0.9248(9) 0.2249(4) 0.0349(17) Uani 1 1 d . . . . .
C21 C 0.9098(8) 1.0839(10) 0.1773(5) 0.053(2) Uani 1 1 d . . . . .
H21A H 0.8551 1.0736 0.1236 0.079 Uiso 1 1 calc R U . . .
H21B H 0.9869 1.1023 0.1719 0.079 Uiso 1 1 calc R U . . .
H21C H 0.8882 1.1782 0.2057 0.079 Uiso 1 1 calc R U . . .
C22 C 1.0512(6) 0.7207(9) 0.1883(4) 0.0340(17) Uani 1 1 d . . . . .
H22 H 1.0642 0.8099 0.1515 0.041 Uiso 1 1 calc R U . . .
C23 C 1.1538(6) 0.7254(9) 0.2649(5) 0.0355(18) Uani 1 1 d . . . . .
C24 C 1.2305(7) 0.8632(11) 0.2764(5) 0.053(2) Uani 1 1 d . . . . .
H24 H 1.2142 0.9525 0.2388 0.063 Uiso 1 1 calc R U . . .
C25 C 1.3295(7) 0.8693(12) 0.3419(5) 0.057(3) Uani 1 1 d . . . . .
H25 H 1.3782 0.9636 0.3483 0.068 Uiso 1 1 calc R U . . .
C26 C 1.3586(7) 0.7383(11) 0.3987(5) 0.048(2) Uani 1 1 d . . . . .
C27 C 1.4760(9) 0.7415(16) 0.4682(6) 0.076(3) Uani 1 1 d . . . . .
H27A H 1.5343 0.7982 0.4488 0.114 Uiso 1 1 calc R U . . .
H27B H 1.5008 0.6271 0.4837 0.114 Uiso 1 1 calc R U . . .
H27C H 1.4656 0.8010 0.5150 0.114 Uiso 1 1 calc R U . . .
C28 C 1.2824(7) 0.6039(11) 0.3885(5) 0.050(2) Uani 1 1 d . . . . .
H28 H 1.2988 0.5157 0.4266 0.060 Uiso 1 1 calc R U . . .
C29 C 1.1824(7) 0.5965(10) 0.3234(5) 0.047(2) Uani 1 1 d . . . . .
H29 H 1.1329 0.5033 0.3184 0.056 Uiso 1 1 calc R U . . .
C30 C 0.7387(7) 0.5879(10) -0.0949(4) 0.0399(19) Uani 1 1 d . . . . .
C31 C 0.6337(7) 0.6455(10) -0.1586(4) 0.0399(19) Uani 1 1 d . . . . .
C32 C 0.5252(7) 0.5687(12) -0.1711(5) 0.056(2) Uani 1 1 d . . . . .
H32 H 0.5151 0.4876 -0.1337 0.067 Uiso 1 1 calc R U . . .
C33 C 0.4318(8) 0.6107(13) -0.2383(6) 0.060(3) Uani 1 1 d . . . . .
H33 H 0.3596 0.5587 -0.2451 0.072 Uiso 1 1 calc R U . . .
C34 C 0.4448(7) 0.7275(11) -0.2944(5) 0.048(2) Uani 1 1 d . . . . .
C35 C 0.2559(9) 0.6759(16) -0.3852(7) 0.093(4) Uani 1 1 d . . . . .
H35A H 0.2746 0.5573 -0.3855 0.139 Uiso 1 1 calc R U . . .
H35B H 0.2075 0.7085 -0.4387 0.139 Uiso 1 1 calc R U . . .
H35C H 0.2148 0.6962 -0.3450 0.139 Uiso 1 1 calc R U . . .
C36 C 0.5513(8) 0.8112(11) -0.2810(5) 0.049(2) Uani 1 1 d . . . . .
H36 H 0.5597 0.8955 -0.3173 0.059 Uiso 1 1 calc R U . . .
C37 C 0.6436(7) 0.7705(10) -0.2148(5) 0.045(2) Uani 1 1 d . . . . .
H37 H 0.7143 0.8271 -0.2071 0.054 Uiso 1 1 calc R U . . .
N1 N 0.9146(5) 0.5437(8) 0.0936(4) 0.0348(15) Uani 1 1 d . . . . .
N2 N 1.1910(7) 0.5466(10) 0.0580(4) 0.057(2) Uani 1 1 d . . . . .
N3 N 0.8947(5) 0.9299(8) 0.2965(4) 0.0383(15) Uani 1 1 d . . . . .
N4 N 0.8917(5) 0.7587(8) 0.3247(4) 0.0359(15) Uani 1 1 d . . . . .
N5 N 0.8379(7) 0.6287(10) -0.1046(4) 0.055(2) Uani 1 1 d . . . . .
O1 O 0.9053(4) 0.4884(6) 0.2748(3) 0.0388(13) Uani 1 1 d . . . . .
O2 O 0.9268(5) 0.5468(10) -0.0433(3) 0.0642(19) Uani 1 1 d . . . . .
O3 O 0.3613(5) 0.7735(8) -0.3650(4) 0.0599(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 1.470(9) . ?
C1 C2 1.536(10) . ?
C1 C19 1.546(10) . ?
C1 H1 0.9800 . ?
C2 C3 1.363(10) . ?
C2 C7 1.389(10) . ?
C3 C4 1.398(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.514(11) . ?
C8 C30 1.522(11) . ?
C8 C9 1.556(10) . ?
C8 H8 0.9800 . ?
C9 N1 1.396(9) . ?
C9 O2 1.457(10) . ?
C9 H9 0.9800 . ?
C10 C11 1.453(11) . ?
C10 N1 1.466(9) . ?
C10 C22 1.555(10) . ?
C10 H10 0.9800 . ?
C11 N2 1.133(10) . ?
C12 C13 1.376(11) . ?
C12 C17 1.387(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(11) . ?
C16 H16 0.9300 . ?
C17 N4 1.394(9) . ?
C18 O1 1.237(8) . ?
C18 N4 1.375(9) . ?
C18 C19 1.503(10) . ?
C19 C20 1.499(10) . ?
C19 C22 1.577(10) . ?
C20 N3 1.273(9) . ?
C20 C21 1.490(11) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.509(10) . ?
C22 H22 0.9800 . ?
C23 C29 1.391(10) . ?
C23 C24 1.397(11) . ?
C24 C25 1.371(12) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(12) . ?
C25 H25 0.9300 . ?
C26 C28 1.373(11) . ?
C26 C27 1.551(12) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.375(11) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N5 1.280(10) . ?
C30 C31 1.472(11) . ?
C31 C32 1.389(11) . ?
C31 C37 1.398(11) . ?
C32 C33 1.387(12) . ?
C32 H32 0.9300 . ?
C33 C34 1.363(12) . ?
C33 H33 0.9300 . ?
C34 O3 1.368(10) . ?
C34 C36 1.391(12) . ?
C35 O3 1.429(11) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.366(11) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
N3 N4 1.434(9) . ?
N5 O2 1.410(9) . ?

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 C2 107.1(5) . . ?
N1 C1 C19 102.6(5) . . ?
C2 C1 C19 116.6(6) . . ?
N1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C19 C1 H1 110.0 . . ?
C3 C2 C7 120.9(7) . . ?
C3 C2 C1 123.2(7) . . ?
C7 C2 C1 115.8(7) . . ?
C2 C3 C4 120.5(8) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.9(8) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.1(9) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.1(8) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 117.4(7) . . ?
C2 C7 C8 121.3(7) . . ?
C6 C7 C8 121.3(7) . . ?
C7 C8 C30 116.9(6) . . ?
C7 C8 C9 113.3(6) . . ?
C30 C8 C9 100.3(6) . . ?
C7 C8 H8 108.6 . . ?
C30 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
N1 C9 O2 112.0(6) . . ?
N1 C9 C8 112.5(6) . . ?
O2 C9 C8 103.7(6) . . ?
N1 C9 H9 109.5 . . ?
O2 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C11 C10 N1 116.4(6) . . ?
C11 C10 C22 109.1(6) . . ?
N1 C10 C22 104.1(5) . . ?
C11 C10 H10 109.0 . . ?
N1 C10 H10 109.0 . . ?
C22 C10 H10 109.0 . . ?
N2 C11 C10 176.7(8) . . ?
C13 C12 C17 118.9(8) . . ?
C13 C12 H12 120.5 . . ?
C17 C12 H12 120.5 . . ?
C14 C13 C12 122.0(8) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.1(8) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 120.4(9) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 119.7(7) . . ?
C16 C17 N4 120.1(6) . . ?
C12 C17 N4 120.1(7) . . ?
O1 C18 N4 124.4(7) . . ?
O1 C18 C19 129.0(7) . . ?
N4 C18 C19 106.5(6) . . ?
C20 C19 C18 101.2(6) . . ?
C20 C19 C1 117.9(6) . . ?
C18 C19 C1 115.8(6) . . ?
C20 C19 C22 111.3(6) . . ?
C18 C19 C22 111.6(5) . . ?
C1 C19 C22 99.4(5) . . ?
N3 C20 C21 120.8(7) . . ?
N3 C20 C19 113.1(6) . . ?
C21 C20 C19 126.1(7) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 113.9(6) . . ?
C23 C22 C19 118.7(6) . . ?
C10 C22 C19 102.5(5) . . ?
C23 C22 H22 107.0 . . ?
C10 C22 H22 107.0 . . ?
C19 C22 H22 107.0 . . ?
C29 C23 C24 116.7(7) . . ?
C29 C23 C22 124.7(6) . . ?
C24 C23 C22 118.5(7) . . ?
C25 C24 C23 121.2(8) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 121.6(8) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C28 C26 C25 117.4(7) . . ?
C28 C26 C27 122.0(8) . . ?
C25 C26 C27 120.6(8) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 121.7(7) . . ?
C26 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C23 121.4(7) . . ?
C28 C29 H29 119.3 . . ?
C23 C29 H29 119.3 . . ?
N5 C30 C31 117.0(7) . . ?
N5 C30 C8 114.8(7) . . ?
C31 C30 C8 127.9(7) . . ?
C32 C31 C37 117.3(7) . . ?
C32 C31 C30 122.6(7) . . ?
C37 C31 C30 119.8(7) . . ?
C33 C32 C31 121.1(8) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C32 120.6(8) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 O3 126.0(8) . . ?
C33 C34 C36 119.1(8) . . ?
O3 C34 C36 114.9(7) . . ?
O3 C35 H35A 109.5 . . ?
O3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C34 120.5(8) . . ?
C37 C36 H36 119.8 . . ?
C34 C36 H36 119.8 . . ?
C36 C37 C31 121.3(7) . . ?
C36 C37 H37 119.4 . . ?
C31 C37 H37 119.4 . . ?
C9 N1 C10 120.1(6) . . ?
C9 N1 C1 120.4(5) . . ?
C10 N1 C1 111.3(5) . . ?
C20 N3 N4 108.1(6) . . ?
C18 N4 C17 129.8(6) . . ?
C18 N4 N3 110.8(6) . . ?
C17 N4 N3 119.4(6) . . ?
C30 N5 O2 108.6(7) . . ?
N5 O2 C9 111.4(6) . . ?
C34 O3 C35 116.0(7) . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_3o
_database_code_depnum_ccdc_archive 'CCDC 1937509'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H25 Br Cl N5 O2'
_chemical_formula_sum            'C35 H25 Br Cl N5 O2'
_chemical_formula_weight         662.96

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'
Br Br -0.2901 2.4595 '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                   7.9255(10)
_cell_length_b                   12.9254(15)
_cell_length_c                   15.224(2)
_cell_angle_alpha                92.788(4)
_cell_angle_beta                 101.518(4)
_cell_angle_gamma                99.593(4)
_cell_volume                     1501.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6354
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             676
_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    1.500
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21617
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5897
_reflns_number_gt                3644
_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)+(0.0738P)²+3.7563P] 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         5897
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2009
_refine_ls_wR_factor_gt          0.1710
_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
Br1 Br 1.26623(11) 0.05878(7) -0.34903(7) 0.1052(4) Uani 1 1 d . . . . .
C1 C 0.8561(5) 0.2643(3) 0.0590(3) 0.0342(10) Uani 1 1 d . . . . .
H1 H 0.9724 0.2871 0.0462 0.041 Uiso 1 1 calc R U . . .
C2 C 0.8041(5) 0.1480(3) 0.0328(3) 0.0342(10) Uani 1 1 d . . . . .
C3 C 0.8687(6) 0.0748(4) 0.0880(3) 0.0424(11) Uani 1 1 d . . . . .
H3 H 0.9420 0.0977 0.1436 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8253(7) -0.0318(4) 0.0614(3) 0.0480(12) Uani 1 1 d . . . . .
H4 H 0.8705 -0.0797 0.0989 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7161(6) -0.0673(4) -0.0200(3) 0.0468(12) Uani 1 1 d . . . . .
H5 H 0.6870 -0.1390 -0.0377 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6500(6) 0.0039(4) -0.0750(3) 0.0451(11) Uani 1 1 d . . . . .
H6 H 0.5735 -0.0204 -0.1296 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6952(5) 0.1115(4) -0.0508(3) 0.0369(10) Uani 1 1 d . . . . .
C8 C 0.6231(6) 0.1891(4) -0.1122(3) 0.0428(11) Uani 1 1 d . . . . .
H8 H 0.5108 0.1542 -0.1498 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5961(7) 0.2877(4) -0.0651(3) 0.0475(12) Uani 1 1 d . . . . .
H9 H 0.4837 0.2768 -0.0462 0.057 Uiso 1 1 calc R U . . .
C10 C 0.7128(6) 0.4147(3) 0.0662(3) 0.0368(10) Uani 1 1 d . . . . .
H10 H 0.5952 0.3998 0.0791 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7369(6) 0.5163(4) 0.0259(3) 0.0455(11) Uani 1 1 d . . . . .
C12 C 0.8297(8) 0.2238(5) 0.4447(3) 0.0672(16) Uani 1 1 d . . . . .
H12 H 0.9498 0.2454 0.4512 0.081 Uiso 1 1 calc R U . . .
C13 C 0.7584(10) 0.2091(6) 0.5198(4) 0.094(2) Uani 1 1 d . . . . .
H13 H 0.8309 0.2201 0.5768 0.112 Uiso 1 1 calc R U . . .
C14 C 0.5831(11) 0.1785(7) 0.5108(5) 0.103(3) Uani 1 1 d . . . . .
H14 H 0.5356 0.1697 0.5617 0.124 Uiso 1 1 calc R U . . .
C15 C 0.4768(9) 0.1606(6) 0.4276(4) 0.087(2) Uani 1 1 d . . . . .
H15 H 0.3569 0.1392 0.4220 0.104 Uiso 1 1 calc R U . . .
C16 C 0.5452(7) 0.1741(4) 0.3511(4) 0.0586(14) Uani 1 1 d . . . . .
H16 H 0.4719 0.1612 0.2944 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7222(6) 0.2066(4) 0.3599(3) 0.0419(11) Uani 1 1 d . . . . .
C18 C 0.7180(5) 0.2475(3) 0.1998(3) 0.0309(9) Uani 1 1 d . . . . .
C19 C 0.8660(5) 0.2995(3) 0.1586(3) 0.0299(9) Uani 1 1 d . . . . .
C20 C 1.0218(5) 0.2860(3) 0.2267(3) 0.0350(10) Uani 1 1 d . . . . .
C21 C 1.2074(6) 0.3175(5) 0.2190(3) 0.0562(14) Uani 1 1 d . . . . .
H21A H 1.2833 0.3125 0.2756 0.084 Uiso 1 1 calc R U . . .
H21B H 1.2265 0.3887 0.2028 0.084 Uiso 1 1 calc R U . . .
H21C H 1.2319 0.2715 0.1735 0.084 Uiso 1 1 calc R U . . .
C22 C 0.8508(5) 0.4189(3) 0.1545(3) 0.0336(9) Uani 1 1 d . . . . .
H22 H 0.9623 0.4573 0.1450 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8125(6) 0.4700(3) 0.2375(3) 0.0348(10) Uani 1 1 d . . . . .
C24 C 0.6456(6) 0.4817(4) 0.2466(3) 0.0472(12) Uani 1 1 d . . . . .
H24 H 0.5515 0.4598 0.1984 0.057 Uiso 1 1 calc R U . . .
C25 C 0.6165(7) 0.5248(4) 0.3254(4) 0.0580(14) Uani 1 1 d . . . . .
H25 H 0.5044 0.5339 0.3298 0.070 Uiso 1 1 calc R U . . .
C26 C 0.7539(7) 0.5545(4) 0.3977(3) 0.0527(13) Uani 1 1 d . . . . .
C27 C 0.9206(7) 0.5464(4) 0.3907(3) 0.0517(13) Uani 1 1 d . . . . .
H27 H 1.0138 0.5688 0.4392 0.062 Uiso 1 1 calc R U . . .
C28 C 0.9492(6) 0.5046(4) 0.3112(3) 0.0440(11) Uani 1 1 d . . . . .
H28 H 1.0628 0.4994 0.3066 0.053 Uiso 1 1 calc R U . . .
C29 C 0.7382(7) 0.2409(4) -0.1731(3) 0.0459(12) Uani 1 1 d . . . . .
C30 C 0.8618(7) 0.1944(4) -0.2159(3) 0.0453(12) Uani 1 1 d . . . . .
C31 C 0.8224(7) 0.0923(4) -0.2559(3) 0.0514(12) Uani 1 1 d . . . . .
H31 H 0.7145 0.0507 -0.2563 0.062 Uiso 1 1 calc R U . . .
C32 C 0.9433(7) 0.0521(4) -0.2954(4) 0.0564(14) Uani 1 1 d . . . . .
H32 H 0.9179 -0.0168 -0.3215 0.068 Uiso 1 1 calc R U . . .
C33 C 1.1009(7) 0.1148(4) -0.2957(4) 0.0571(14) Uani 1 1 d . . . . .
C34 C 1.1430(8) 0.2155(4) -0.2564(4) 0.0609(15) Uani 1 1 d . . . . .
H34 H 1.2504 0.2569 -0.2572 0.073 Uiso 1 1 calc R U . . .
C35 C 1.0248(8) 0.2544(4) -0.2159(3) 0.0555(14) Uani 1 1 d . . . . .
H35 H 1.0540 0.3224 -0.1878 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7156(2) 0.60613(16) 0.49826(11) 0.0939(6) Uani 1 1 d . . . . .
N1 N 0.7372(5) 0.3283(3) 0.0091(2) 0.0414(9) Uani 1 1 d . . . . .
N2 N 0.7539(6) 0.5964(4) -0.0018(3) 0.0654(13) Uani 1 1 d . . . . .
N3 N 0.9824(5) 0.2469(3) 0.2975(2) 0.0398(9) Uani 1 1 d . . . . .
N4 N 0.7971(4) 0.2248(3) 0.2841(2) 0.0348(8) Uani 1 1 d . . . . .
N5 N 0.7167(7) 0.3353(4) -0.1859(3) 0.0633(13) Uani 1 1 d . . . . .
O1 O 0.5616(4) 0.2343(2) 0.16801(19) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.5977(5) 0.3620(3) -0.1332(2) 0.0647(11) 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
Br1 C33 1.893(5) . ?
C1 N1 1.478(5) . ?
C1 C2 1.503(6) . ?
C1 C19 1.545(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.390(6) . ?
C2 C7 1.397(6) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.510(6) . ?
C8 C9 1.498(7) . ?
C8 C29 1.529(7) . ?
C8 H8 0.9800 . ?
C9 N1 1.430(6) . ?
C9 O2 1.447(6) . ?
C9 H9 0.9800 . ?
C10 N1 1.444(5) . ?
C10 C11 1.476(6) . ?
C10 C22 1.546(6) . ?
C10 H10 0.9800 . ?
C11 N2 1.135(6) . ?
C12 C13 1.380(8) . ?
C12 C17 1.382(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(7) . ?
C16 H16 0.9300 . ?
C17 N4 1.412(6) . ?
C18 O1 1.217(5) . ?
C18 N4 1.379(5) . ?
C18 C19 1.515(6) . ?
C19 C20 1.486(6) . ?
C19 C22 1.571(6) . ?
C20 N3 1.284(6) . ?
C20 C21 1.489(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.505(6) . ?
C22 H22 0.9800 . ?
C23 C24 1.389(6) . ?
C23 C28 1.392(6) . ?
C24 C25 1.376(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.367(7) . ?
C26 Cl1 1.743(5) . ?
C27 C28 1.377(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 N5 1.278(6) . ?
C29 C30 1.469(7) . ?
C30 C31 1.386(7) . ?
C30 C35 1.392(7) . ?
C31 C32 1.384(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(8) . ?
C34 C35 1.367(8) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N3 N4 1.419(5) . ?
N5 O2 1.427(6) . ?

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 C2 114.1(3) . . ?
N1 C1 C19 103.6(3) . . ?
C2 C1 C19 116.1(3) . . ?
N1 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C19 C1 H1 107.5 . . ?
C3 C2 C7 118.4(4) . . ?
C3 C2 C1 121.6(4) . . ?
C7 C2 C1 120.0(4) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 119.6(4) . . ?
C6 C7 C8 120.8(4) . . ?
C2 C7 C8 119.6(4) . . ?
C9 C8 C7 114.9(4) . . ?
C9 C8 C29 97.8(4) . . ?
C7 C8 C29 117.6(4) . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C29 C8 H8 108.6 . . ?
N1 C9 O2 107.8(4) . . ?
N1 C9 C8 112.5(4) . . ?
O2 C9 C8 103.2(4) . . ?
N1 C9 H9 111.0 . . ?
O2 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
N1 C10 C11 112.7(4) . . ?
N1 C10 C22 105.7(3) . . ?
C11 C10 C22 110.1(4) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C22 C10 H10 109.4 . . ?
N2 C11 C10 177.0(5) . . ?
C13 C12 C17 119.9(6) . . ?
C13 C12 H12 120.1 . . ?
C17 C12 H12 120.1 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.7(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 119.6(5) . . ?
C16 C17 N4 121.4(4) . . ?
C12 C17 N4 119.0(4) . . ?
O1 C18 N4 127.0(4) . . ?
O1 C18 C19 127.6(4) . . ?
N4 C18 C19 105.4(3) . . ?
C20 C19 C18 101.5(3) . . ?
C20 C19 C1 118.6(3) . . ?
C18 C19 C1 116.2(3) . . ?
C20 C19 C22 111.2(3) . . ?
C18 C19 C22 107.0(3) . . ?
C1 C19 C22 102.2(3) . . ?
N3 C20 C19 113.1(4) . . ?
N3 C20 C21 121.3(4) . . ?
C19 C20 C21 125.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 116.6(3) . . ?
C23 C22 C19 115.1(3) . . ?
C10 C22 C19 101.1(3) . . ?
C23 C22 H22 107.8 . . ?
C10 C22 H22 107.8 . . ?
C19 C22 H22 107.8 . . ?
C24 C23 C28 117.2(4) . . ?
C24 C23 C22 123.7(4) . . ?
C28 C23 C22 119.1(4) . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C24 119.6(5) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 Cl1 119.8(4) . . ?
C25 C26 Cl1 119.5(4) . . ?
C26 C27 C28 119.3(5) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C23 121.7(5) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?
N5 C29 C30 120.1(5) . . ?
N5 C29 C8 112.3(4) . . ?
C30 C29 C8 127.7(4) . . ?
C31 C30 C35 118.6(5) . . ?
C31 C30 C29 122.3(5) . . ?
C35 C30 C29 119.1(4) . . ?
C32 C31 C30 120.1(5) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 119.4(5) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 121.6(5) . . ?
C34 C33 Br1 119.3(4) . . ?
C32 C33 Br1 119.1(4) . . ?
C33 C34 C35 119.0(5) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C34 C35 C30 121.3(5) . . ?
C34 C35 H35 119.3 . . ?
C30 C35 H35 119.3 . . ?
C9 N1 C10 116.7(4) . . ?
C9 N1 C1 124.4(4) . . ?
C10 N1 C1 111.7(3) . . ?
C20 N3 N4 107.8(3) . . ?
C18 N4 C17 128.5(4) . . ?
C18 N4 N3 111.7(3) . . ?
C17 N4 N3 118.2(3) . . ?
C29 N5 O2 108.3(4) . . ?
N5 O2 C9 106.3(3) . . ?

_refine_diff_density_max         1.784
_refine_diff_density_min         -1.588
_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_3p
_database_code_depnum_ccdc_archive 'CCDC 1937601'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H25 Br Cl N5 O2'
_chemical_formula_sum            'C35 H25 Br Cl N5 O2'
_chemical_formula_weight         662.96

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'
Br Br -0.2901 2.4595 '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                   7.9255(10)
_cell_length_b                   12.9254(15)
_cell_length_c                   15.224(2)
_cell_angle_alpha                92.788(4)
_cell_angle_beta                 101.518(4)
_cell_angle_gamma                99.593(4)
_cell_volume                     1501.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6354
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             676
_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    1.500
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21617
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5897
_reflns_number_gt                3644
_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)+(0.0738P)²+3.7563P] 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         5897
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2009
_refine_ls_wR_factor_gt          0.1710
_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
Br1 Br 1.26623(11) 0.05878(7) -0.34903(7) 0.1052(4) Uani 1 1 d . . . . .
C1 C 0.8561(5) 0.2643(3) 0.0590(3) 0.0342(10) Uani 1 1 d . . . . .
H1 H 0.9724 0.2871 0.0462 0.041 Uiso 1 1 calc R U . . .
C2 C 0.8041(5) 0.1480(3) 0.0328(3) 0.0342(10) Uani 1 1 d . . . . .
C3 C 0.8687(6) 0.0748(4) 0.0880(3) 0.0424(11) Uani 1 1 d . . . . .
H3 H 0.9420 0.0977 0.1436 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8253(7) -0.0318(4) 0.0614(3) 0.0480(12) Uani 1 1 d . . . . .
H4 H 0.8705 -0.0797 0.0989 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7161(6) -0.0673(4) -0.0200(3) 0.0468(12) Uani 1 1 d . . . . .
H5 H 0.6870 -0.1390 -0.0377 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6500(6) 0.0039(4) -0.0750(3) 0.0451(11) Uani 1 1 d . . . . .
H6 H 0.5735 -0.0204 -0.1296 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6952(5) 0.1115(4) -0.0508(3) 0.0369(10) Uani 1 1 d . . . . .
C8 C 0.6231(6) 0.1891(4) -0.1122(3) 0.0428(11) Uani 1 1 d . . . . .
H8 H 0.5108 0.1542 -0.1498 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5961(7) 0.2877(4) -0.0651(3) 0.0475(12) Uani 1 1 d . . . . .
H9 H 0.4837 0.2768 -0.0462 0.057 Uiso 1 1 calc R U . . .
C10 C 0.7128(6) 0.4147(3) 0.0662(3) 0.0368(10) Uani 1 1 d . . . . .
H10 H 0.5952 0.3998 0.0791 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7369(6) 0.5163(4) 0.0259(3) 0.0455(11) Uani 1 1 d . . . . .
C12 C 0.8297(8) 0.2238(5) 0.4447(3) 0.0672(16) Uani 1 1 d . . . . .
H12 H 0.9498 0.2454 0.4512 0.081 Uiso 1 1 calc R U . . .
C13 C 0.7584(10) 0.2091(6) 0.5198(4) 0.094(2) Uani 1 1 d . . . . .
H13 H 0.8309 0.2201 0.5768 0.112 Uiso 1 1 calc R U . . .
C14 C 0.5831(11) 0.1785(7) 0.5108(5) 0.103(3) Uani 1 1 d . . . . .
H14 H 0.5356 0.1697 0.5617 0.124 Uiso 1 1 calc R U . . .
C15 C 0.4768(9) 0.1606(6) 0.4276(4) 0.087(2) Uani 1 1 d . . . . .
H15 H 0.3569 0.1392 0.4220 0.104 Uiso 1 1 calc R U . . .
C16 C 0.5452(7) 0.1741(4) 0.3511(4) 0.0586(14) Uani 1 1 d . . . . .
H16 H 0.4719 0.1612 0.2944 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7222(6) 0.2066(4) 0.3599(3) 0.0419(11) Uani 1 1 d . . . . .
C18 C 0.7180(5) 0.2475(3) 0.1998(3) 0.0309(9) Uani 1 1 d . . . . .
C19 C 0.8660(5) 0.2995(3) 0.1586(3) 0.0299(9) Uani 1 1 d . . . . .
C20 C 1.0218(5) 0.2860(3) 0.2267(3) 0.0350(10) Uani 1 1 d . . . . .
C21 C 1.2074(6) 0.3175(5) 0.2190(3) 0.0562(14) Uani 1 1 d . . . . .
H21A H 1.2833 0.3125 0.2756 0.084 Uiso 1 1 calc R U . . .
H21B H 1.2265 0.3887 0.2028 0.084 Uiso 1 1 calc R U . . .
H21C H 1.2319 0.2715 0.1735 0.084 Uiso 1 1 calc R U . . .
C22 C 0.8508(5) 0.4189(3) 0.1545(3) 0.0336(9) Uani 1 1 d . . . . .
H22 H 0.9623 0.4573 0.1450 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8125(6) 0.4700(3) 0.2375(3) 0.0348(10) Uani 1 1 d . . . . .
C24 C 0.6456(6) 0.4817(4) 0.2466(3) 0.0472(12) Uani 1 1 d . . . . .
H24 H 0.5515 0.4598 0.1984 0.057 Uiso 1 1 calc R U . . .
C25 C 0.6165(7) 0.5248(4) 0.3254(4) 0.0580(14) Uani 1 1 d . . . . .
H25 H 0.5044 0.5339 0.3298 0.070 Uiso 1 1 calc R U . . .
C26 C 0.7539(7) 0.5545(4) 0.3977(3) 0.0527(13) Uani 1 1 d . . . . .
C27 C 0.9206(7) 0.5464(4) 0.3907(3) 0.0517(13) Uani 1 1 d . . . . .
H27 H 1.0138 0.5688 0.4392 0.062 Uiso 1 1 calc R U . . .
C28 C 0.9492(6) 0.5046(4) 0.3112(3) 0.0440(11) Uani 1 1 d . . . . .
H28 H 1.0628 0.4994 0.3066 0.053 Uiso 1 1 calc R U . . .
C29 C 0.7382(7) 0.2409(4) -0.1731(3) 0.0459(12) Uani 1 1 d . . . . .
C30 C 0.8618(7) 0.1944(4) -0.2159(3) 0.0453(12) Uani 1 1 d . . . . .
C31 C 0.8224(7) 0.0923(4) -0.2559(3) 0.0514(12) Uani 1 1 d . . . . .
H31 H 0.7145 0.0507 -0.2563 0.062 Uiso 1 1 calc R U . . .
C32 C 0.9433(7) 0.0521(4) -0.2954(4) 0.0564(14) Uani 1 1 d . . . . .
H32 H 0.9179 -0.0168 -0.3215 0.068 Uiso 1 1 calc R U . . .
C33 C 1.1009(7) 0.1148(4) -0.2957(4) 0.0571(14) Uani 1 1 d . . . . .
C34 C 1.1430(8) 0.2155(4) -0.2564(4) 0.0609(15) Uani 1 1 d . . . . .
H34 H 1.2504 0.2569 -0.2572 0.073 Uiso 1 1 calc R U . . .
C35 C 1.0248(8) 0.2544(4) -0.2159(3) 0.0555(14) Uani 1 1 d . . . . .
H35 H 1.0540 0.3224 -0.1878 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7156(2) 0.60613(16) 0.49826(11) 0.0939(6) Uani 1 1 d . . . . .
N1 N 0.7372(5) 0.3283(3) 0.0091(2) 0.0414(9) Uani 1 1 d . . . . .
N2 N 0.7539(6) 0.5964(4) -0.0018(3) 0.0654(13) Uani 1 1 d . . . . .
N3 N 0.9824(5) 0.2469(3) 0.2975(2) 0.0398(9) Uani 1 1 d . . . . .
N4 N 0.7971(4) 0.2248(3) 0.2841(2) 0.0348(8) Uani 1 1 d . . . . .
N5 N 0.7167(7) 0.3353(4) -0.1859(3) 0.0633(13) Uani 1 1 d . . . . .
O1 O 0.5616(4) 0.2343(2) 0.16801(19) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.5977(5) 0.3620(3) -0.1332(2) 0.0647(11) 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
Br1 C33 1.893(5) . ?
C1 N1 1.478(5) . ?
C1 C2 1.503(6) . ?
C1 C19 1.545(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.390(6) . ?
C2 C7 1.397(6) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.510(6) . ?
C8 C9 1.498(7) . ?
C8 C29 1.529(7) . ?
C8 H8 0.9800 . ?
C9 N1 1.430(6) . ?
C9 O2 1.447(6) . ?
C9 H9 0.9800 . ?
C10 N1 1.444(5) . ?
C10 C11 1.476(6) . ?
C10 C22 1.546(6) . ?
C10 H10 0.9800 . ?
C11 N2 1.135(6) . ?
C12 C13 1.380(8) . ?
C12 C17 1.382(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(7) . ?
C16 H16 0.9300 . ?
C17 N4 1.412(6) . ?
C18 O1 1.217(5) . ?
C18 N4 1.379(5) . ?
C18 C19 1.515(6) . ?
C19 C20 1.486(6) . ?
C19 C22 1.571(6) . ?
C20 N3 1.284(6) . ?
C20 C21 1.489(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.505(6) . ?
C22 H22 0.9800 . ?
C23 C24 1.389(6) . ?
C23 C28 1.392(6) . ?
C24 C25 1.376(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.367(7) . ?
C26 Cl1 1.743(5) . ?
C27 C28 1.377(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 N5 1.278(6) . ?
C29 C30 1.469(7) . ?
C30 C31 1.386(7) . ?
C30 C35 1.392(7) . ?
C31 C32 1.384(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(8) . ?
C34 C35 1.367(8) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N3 N4 1.419(5) . ?
N5 O2 1.427(6) . ?

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 C2 114.1(3) . . ?
N1 C1 C19 103.6(3) . . ?
C2 C1 C19 116.1(3) . . ?
N1 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C19 C1 H1 107.5 . . ?
C3 C2 C7 118.4(4) . . ?
C3 C2 C1 121.6(4) . . ?
C7 C2 C1 120.0(4) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 119.6(4) . . ?
C6 C7 C8 120.8(4) . . ?
C2 C7 C8 119.6(4) . . ?
C9 C8 C7 114.9(4) . . ?
C9 C8 C29 97.8(4) . . ?
C7 C8 C29 117.6(4) . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C29 C8 H8 108.6 . . ?
N1 C9 O2 107.8(4) . . ?
N1 C9 C8 112.5(4) . . ?
O2 C9 C8 103.2(4) . . ?
N1 C9 H9 111.0 . . ?
O2 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
N1 C10 C11 112.7(4) . . ?
N1 C10 C22 105.7(3) . . ?
C11 C10 C22 110.1(4) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C22 C10 H10 109.4 . . ?
N2 C11 C10 177.0(5) . . ?
C13 C12 C17 119.9(6) . . ?
C13 C12 H12 120.1 . . ?
C17 C12 H12 120.1 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.7(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 119.6(5) . . ?
C16 C17 N4 121.4(4) . . ?
C12 C17 N4 119.0(4) . . ?
O1 C18 N4 127.0(4) . . ?
O1 C18 C19 127.6(4) . . ?
N4 C18 C19 105.4(3) . . ?
C20 C19 C18 101.5(3) . . ?
C20 C19 C1 118.6(3) . . ?
C18 C19 C1 116.2(3) . . ?
C20 C19 C22 111.2(3) . . ?
C18 C19 C22 107.0(3) . . ?
C1 C19 C22 102.2(3) . . ?
N3 C20 C19 113.1(4) . . ?
N3 C20 C21 121.3(4) . . ?
C19 C20 C21 125.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 116.6(3) . . ?
C23 C22 C19 115.1(3) . . ?
C10 C22 C19 101.1(3) . . ?
C23 C22 H22 107.8 . . ?
C10 C22 H22 107.8 . . ?
C19 C22 H22 107.8 . . ?
C24 C23 C28 117.2(4) . . ?
C24 C23 C22 123.7(4) . . ?
C28 C23 C22 119.1(4) . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C24 119.6(5) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 Cl1 119.8(4) . . ?
C25 C26 Cl1 119.5(4) . . ?
C26 C27 C28 119.3(5) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C23 121.7(5) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?
N5 C29 C30 120.1(5) . . ?
N5 C29 C8 112.3(4) . . ?
C30 C29 C8 127.7(4) . . ?
C31 C30 C35 118.6(5) . . ?
C31 C30 C29 122.3(5) . . ?
C35 C30 C29 119.1(4) . . ?
C32 C31 C30 120.1(5) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 119.4(5) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 121.6(5) . . ?
C34 C33 Br1 119.3(4) . . ?
C32 C33 Br1 119.1(4) . . ?
C33 C34 C35 119.0(5) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C34 C35 C30 121.3(5) . . ?
C34 C35 H35 119.3 . . ?
C30 C35 H35 119.3 . . ?
C9 N1 C10 116.7(4) . . ?
C9 N1 C1 124.4(4) . . ?
C10 N1 C1 111.7(3) . . ?
C20 N3 N4 107.8(3) . . ?
C18 N4 C17 128.5(4) . . ?
C18 N4 N3 111.7(3) . . ?
C17 N4 N3 118.2(3) . . ?
C29 N5 O2 108.3(4) . . ?
N5 O2 C9 106.3(3) . . ?

_refine_diff_density_max         1.784
_refine_diff_density_min         -1.588
_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_5f
_database_code_depnum_ccdc_archive 'CCDC 1937511'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-08 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 H28 N4 O3'
_chemical_formula_sum            'C36 H28 N4 O3'
_chemical_formula_weight         564.62

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'

_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                   9.696(4)
_cell_length_b                   24.284(9)
_cell_length_c                   12.449(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.612(11)
_cell_angle_gamma                90
_cell_volume                     2881(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1717
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      18.96

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1184
_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    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.985
_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_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22936
_diffrn_reflns_av_unetI/netI     0.3141
_diffrn_reflns_av_R_equivalents  0.2547
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.677
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        24.713
_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             4895
_reflns_number_gt                1779
_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)+(0.0754P)²+0.2591P] 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         4895
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2923
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.2236
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.8646(6) 0.1348(2) 0.3645(5) 0.0472(16) Uani 1 1 d . . . . .
H1 H 0.9279 0.1048 0.3533 0.057 Uiso 1 1 calc R U . . .
C2 C 0.9497(6) 0.1805(2) 0.4340(5) 0.0414(15) Uani 1 1 d . . . . .
H2 H 1.0498 0.1715 0.4450 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9080(6) 0.1896(2) 0.5434(5) 0.0390(15) Uani 1 1 d . . . . .
C4 C 1.0063(7) 0.2056(2) 0.6339(6) 0.0523(17) Uani 1 1 d . . . . .
H4 H 1.1004 0.2085 0.6283 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9647(8) 0.2174(2) 0.7336(5) 0.0608(19) Uani 1 1 d . . . . .
H5 H 1.0302 0.2288 0.7938 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8250(8) 0.2119(2) 0.7411(6) 0.0649(19) Uani 1 1 d . . . . .
H6 H 0.7968 0.2202 0.8067 0.078 Uiso 1 1 calc R U . . .
C7 C 0.7271(7) 0.1946(2) 0.6538(5) 0.0500(17) Uani 1 1 d . . . . .
H7 H 0.6336 0.1911 0.6607 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7672(6) 0.1821(2) 0.5552(4) 0.0358(14) Uani 1 1 d . . . . .
C9 C 0.6713(5) 0.1556(2) 0.4605(4) 0.0367(14) Uani 1 1 d . . . . .
H9 H 0.6368 0.1834 0.4050 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6560(5) 0.07271(19) 0.3473(4) 0.0379(15) Uani 1 1 d . . . . .
H10 H 0.6492 0.0807 0.2693 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7198(6) 0.0148(2) 0.3728(5) 0.0453(16) Uani 1 1 d . . . . .
C12 C 0.8253(6) -0.0053(2) 0.3076(5) 0.0408(15) Uani 1 1 d . . . . .
C13 C 0.9206(7) -0.0442(3) 0.3522(6) 0.075(2) Uani 1 1 d . . . . .
H13 H 0.9187 -0.0573 0.4221 0.090 Uiso 1 1 calc R U . . .
C14 C 1.0191(8) -0.0642(3) 0.2961(9) 0.100(3) Uani 1 1 d . . . . .
H14 H 1.0866 -0.0891 0.3294 0.120 Uiso 1 1 calc R U . . .
C15 C 1.0176(8) -0.0473(3) 0.1902(9) 0.090(3) Uani 1 1 d . . . . .
H15 H 1.0835 -0.0614 0.1520 0.108 Uiso 1 1 calc R U . . .
C16 C 0.9208(8) -0.0102(3) 0.1410(6) 0.082(2) Uani 1 1 d . . . . .
H16 H 0.9190 0.0004 0.0690 0.098 Uiso 1 1 calc R U . . .
C17 C 0.8237(6) 0.0118(2) 0.2005(6) 0.0602(18) Uani 1 1 d . . . . .
H17 H 0.7585 0.0378 0.1684 0.072 Uiso 1 1 calc R U . . .
C18 C 0.4273(6) 0.1396(2) 0.2103(5) 0.0492(16) Uani 1 1 d . . . . .
H18 H 0.5193 0.1506 0.2109 0.059 Uiso 1 1 calc R U . . .
C19 C 0.3207(7) 0.1591(2) 0.1296(5) 0.0589(18) Uani 1 1 d . . . . .
H19 H 0.3438 0.1829 0.0770 0.071 Uiso 1 1 calc R U . . .
C20 C 0.1829(7) 0.1450(3) 0.1240(5) 0.0580(18) Uani 1 1 d . . . . .
C21 C 0.0667(7) 0.1670(3) 0.0384(5) 0.094(2) Uani 1 1 d . . . . .
H21A H 0.0347 0.2015 0.0623 0.141 Uiso 1 1 calc R U . . .
H21B H -0.0096 0.1412 0.0266 0.141 Uiso 1 1 calc R U . . .
H21C H 0.1006 0.1724 -0.0286 0.141 Uiso 1 1 calc R U . . .
C22 C 0.1537(7) 0.1098(3) 0.2048(6) 0.0640(19) Uani 1 1 d . . . . .
H22 H 0.0611 0.0997 0.2043 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2577(7) 0.0893(2) 0.2860(5) 0.0522(17) Uani 1 1 d . . . . .
H23 H 0.2336 0.0656 0.3383 0.063 Uiso 1 1 calc R U . . .
C24 C 0.3980(6) 0.1035(2) 0.2909(5) 0.0409(15) Uani 1 1 d . . . . .
C25 C 0.5115(6) 0.0806(2) 0.3796(4) 0.0410(15) Uani 1 1 d . . . . .
H25 H 0.4800 0.0449 0.4031 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5463(6) 0.1203(2) 0.4847(4) 0.0391(15) Uani 1 1 d . . . . .
C27 C 0.4239(7) 0.1539(2) 0.5005(5) 0.0505(17) Uani 1 1 d . . . . .
C28 C 0.5928(6) 0.0857(2) 0.5826(6) 0.0501(17) Uani 1 1 d . . . . .
C29 C 0.9034(7) 0.3319(3) 0.3297(5) 0.0603(18) Uani 1 1 d . . . . .
H29 H 0.8208 0.3271 0.2792 0.072 Uiso 1 1 calc R U . . .
C30 C 0.9563(8) 0.3852(2) 0.3523(6) 0.0639(19) Uani 1 1 d . . . . .
H30 H 0.9080 0.4153 0.3179 0.077 Uiso 1 1 calc R U . . .
C31 C 1.0790(8) 0.3929(3) 0.4249(5) 0.0554(18) Uani 1 1 d . . . . .
C32 C 1.0886(8) 0.4914(2) 0.3942(5) 0.089(2) Uani 1 1 d . . . . .
H32A H 1.1031 0.4883 0.3202 0.134 Uiso 1 1 calc R U . . .
H32B H 1.1370 0.5233 0.4277 0.134 Uiso 1 1 calc R U . . .
H32C H 0.9901 0.4949 0.3947 0.134 Uiso 1 1 calc R U . . .
C33 C 1.1484(6) 0.3488(2) 0.4798(5) 0.0571(18) Uani 1 1 d . . . . .
H33 H 1.2292 0.3545 0.5319 0.068 Uiso 1 1 calc R U . . .
C34 C 1.0964(7) 0.2951(2) 0.4567(5) 0.0522(17) Uani 1 1 d . . . . .
H34 H 1.1453 0.2653 0.4919 0.063 Uiso 1 1 calc R U . . .
C35 C 0.9720(7) 0.2859(2) 0.3814(5) 0.0454(16) Uani 1 1 d . . . . .
C36 C 0.9199(6) 0.2291(2) 0.3569(5) 0.0424(15) Uani 1 1 d . . . . .
N1 N 0.3327(6) 0.1797(2) 0.5136(4) 0.0805(19) Uani 1 1 d . . . . .
N2 N 0.6277(6) 0.0583(2) 0.6579(5) 0.0741(18) Uani 1 1 d . . . . .
N3 N 0.7533(4) 0.11340(16) 0.4137(3) 0.0382(12) Uani 1 1 d . . . . .
N4 N 0.8426(5) 0.2185(2) 0.2636(4) 0.0537(14) Uani 1 1 d . . . . .
O1 O 0.6908(4) -0.01198(16) 0.4472(4) 0.0692(14) Uani 1 1 d . . . . .
O2 O 1.1422(5) 0.44293(18) 0.4545(4) 0.0812(14) Uani 1 1 d . . . . .
O3 O 0.8087(4) 0.16077(17) 0.2588(3) 0.0610(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 N3 1.434(6) . ?
C1 O3 1.469(6) . ?
C1 C2 1.547(7) . ?
C1 H1 0.9800 . ?
C2 C3 1.507(7) . ?
C2 C36 1.517(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.390(7) . ?
C3 C8 1.412(7) . ?
C4 C5 1.404(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(7) . ?
C9 N3 1.480(6) . ?
C9 C26 1.558(7) . ?
C9 H9 0.9800 . ?
C10 N3 1.504(6) . ?
C10 C25 1.539(6) . ?
C10 C11 1.545(7) . ?
C10 H10 0.9800 . ?
C11 O1 1.207(6) . ?
C11 C12 1.500(7) . ?
C12 C13 1.366(7) . ?
C12 C17 1.394(7) . ?
C13 C14 1.372(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.385(7) . ?
C18 C24 1.401(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(7) . ?
C19 H19 0.9300 . ?
C20 C22 1.389(8) . ?
C20 C21 1.500(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.382(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.514(7) . ?
C25 C26 1.611(7) . ?
C25 H25 0.9800 . ?
C26 C28 1.482(8) . ?
C26 C27 1.483(8) . ?
C27 N1 1.120(6) . ?
C28 N2 1.148(7) . ?
C29 C35 1.395(7) . ?
C29 C30 1.401(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.367(8) . ?
C30 H30 0.9300 . ?
C31 C33 1.376(7) . ?
C31 O2 1.381(7) . ?
C32 O2 1.440(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.409(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.403(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.480(7) . ?
C36 N4 1.287(6) . ?
N4 O3 1.438(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 O3 110.8(4) . . ?
N3 C1 C2 112.7(4) . . ?
O3 C1 C2 105.4(4) . . ?
N3 C1 H1 109.3 . . ?
O3 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C3 C2 C36 114.0(4) . . ?
C3 C2 C1 114.1(4) . . ?
C36 C2 C1 100.6(5) . . ?
C3 C2 H2 109.3 . . ?
C36 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C4 C3 C8 119.0(5) . . ?
C4 C3 C2 121.0(6) . . ?
C8 C3 C2 120.0(5) . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.0(6) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 121.4(6) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.1(6) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 119.8(5) . . ?
C7 C8 C9 123.6(5) . . ?
C3 C8 C9 116.3(5) . . ?
N3 C9 C8 107.8(4) . . ?
N3 C9 C26 100.8(4) . . ?
C8 C9 C26 118.3(4) . . ?
N3 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
C26 C9 H9 109.8 . . ?
N3 C10 C25 106.5(4) . . ?
N3 C10 C11 107.3(4) . . ?
C25 C10 C11 114.1(4) . . ?
N3 C10 H10 109.6 . . ?
C25 C10 H10 109.6 . . ?
C11 C10 H10 109.6 . . ?
O1 C11 C12 121.2(5) . . ?
O1 C11 C10 120.5(5) . . ?
C12 C11 C10 118.1(5) . . ?
C13 C12 C17 118.8(6) . . ?
C13 C12 C11 118.9(6) . . ?
C17 C12 C11 122.2(5) . . ?
C12 C13 C14 121.3(7) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 119.8(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.8(7) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.1(7) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.0(6) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C24 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C24 C18 H18 119.6 . . ?
C20 C19 C18 122.8(6) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C22 116.4(6) . . ?
C19 C20 C21 123.1(7) . . ?
C22 C20 C21 120.5(7) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 122.2(6) . . ?
C23 C22 H22 118.9 . . ?
C20 C22 H22 118.9 . . ?
C22 C23 C24 121.2(6) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C18 116.6(6) . . ?
C23 C24 C25 120.9(5) . . ?
C18 C24 C25 122.5(5) . . ?
C24 C25 C10 115.4(5) . . ?
C24 C25 C26 112.7(4) . . ?
C10 C25 C26 102.8(4) . . ?
C24 C25 H25 108.5 . . ?
C10 C25 H25 108.5 . . ?
C26 C25 H25 108.5 . . ?
C28 C26 C27 109.4(4) . . ?
C28 C26 C9 110.0(4) . . ?
C27 C26 C9 113.2(4) . . ?
C28 C26 C25 108.3(4) . . ?
C27 C26 C25 112.6(4) . . ?
C9 C26 C25 103.1(4) . . ?
N1 C27 C26 179.0(7) . . ?
N2 C28 C26 179.1(7) . . ?
C35 C29 C30 121.4(6) . . ?
C35 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C31 C30 C29 120.0(6) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C33 120.6(6) . . ?
C30 C31 O2 125.9(7) . . ?
C33 C31 O2 113.5(7) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 C34 119.6(6) . . ?
C31 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 121.1(6) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C29 C35 C34 117.2(5) . . ?
C29 C35 C36 122.4(6) . . ?
C34 C35 C36 120.4(6) . . ?
N4 C36 C35 119.5(6) . . ?
N4 C36 C2 115.2(5) . . ?
C35 C36 C2 125.3(6) . . ?
C1 N3 C9 114.7(4) . . ?
C1 N3 C10 116.6(4) . . ?
C9 N3 C10 110.1(4) . . ?
C36 N4 O3 108.9(4) . . ?
C31 O2 C32 118.8(6) . . ?
N4 O3 C1 109.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 C3 5.4(7) . . . . ?
O3 C1 C2 C3 126.4(4) . . . . ?
N3 C1 C2 C36 -117.0(5) . . . . ?
O3 C1 C2 C36 4.0(5) . . . . ?
C36 C2 C3 C4 -97.9(6) . . . . ?
C1 C2 C3 C4 147.3(5) . . . . ?
C36 C2 C3 C8 81.8(6) . . . . ?
C1 C2 C3 C8 -32.9(7) . . . . ?
C8 C3 C4 C5 -3.9(7) . . . . ?
C2 C3 C4 C5 175.8(5) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 0.8(9) . . . . ?
C5 C6 C7 C8 -0.1(9) . . . . ?
C6 C7 C8 C3 -2.6(8) . . . . ?
C6 C7 C8 C9 171.4(5) . . . . ?
C4 C3 C8 C7 4.6(7) . . . . ?
C2 C3 C8 C7 -175.1(5) . . . . ?
C4 C3 C8 C9 -169.8(4) . . . . ?
C2 C3 C8 C9 10.4(7) . . . . ?
C7 C8 C9 N3 -137.8(5) . . . . ?
C3 C8 C9 N3 36.4(6) . . . . ?
C7 C8 C9 C26 -24.4(7) . . . . ?
C3 C8 C9 C26 149.8(4) . . . . ?
N3 C10 C11 O1 89.5(6) . . . . ?
C25 C10 C11 O1 -28.2(8) . . . . ?
N3 C10 C11 C12 -86.6(6) . . . . ?
C25 C10 C11 C12 155.7(5) . . . . ?
O1 C11 C12 C13 -21.0(8) . . . . ?
C10 C11 C12 C13 155.1(5) . . . . ?
O1 C11 C12 C17 154.9(6) . . . . ?
C10 C11 C12 C17 -29.0(7) . . . . ?
C17 C12 C13 C14 3.7(10) . . . . ?
C11 C12 C13 C14 179.8(6) . . . . ?
C12 C13 C14 C15 -3.8(11) . . . . ?
C13 C14 C15 C16 1.1(12) . . . . ?
C14 C15 C16 C17 1.5(11) . . . . ?
C13 C12 C17 C16 -1.1(9) . . . . ?
C11 C12 C17 C16 -177.0(5) . . . . ?
C15 C16 C17 C12 -1.5(10) . . . . ?
C24 C18 C19 C20 0.4(9) . . . . ?
C18 C19 C20 C22 0.4(9) . . . . ?
C18 C19 C20 C21 178.6(6) . . . . ?
C19 C20 C22 C23 -0.9(9) . . . . ?
C21 C20 C22 C23 -179.1(5) . . . . ?
C20 C22 C23 C24 0.4(9) . . . . ?
C22 C23 C24 C18 0.4(8) . . . . ?
C22 C23 C24 C25 -179.5(5) . . . . ?
C19 C18 C24 C23 -0.9(8) . . . . ?
C19 C18 C24 C25 179.1(5) . . . . ?
C23 C24 C25 C10 149.2(5) . . . . ?
C18 C24 C25 C10 -30.8(7) . . . . ?
C23 C24 C25 C26 -93.0(6) . . . . ?
C18 C24 C25 C26 87.0(6) . . . . ?
N3 C10 C25 C24 112.8(5) . . . . ?
C11 C10 C25 C24 -129.1(5) . . . . ?
N3 C10 C25 C26 -10.4(5) . . . . ?
C11 C10 C25 C26 107.8(5) . . . . ?
N3 C9 C26 C28 75.1(5) . . . . ?
C8 C9 C26 C28 -42.1(6) . . . . ?
N3 C9 C26 C27 -162.2(4) . . . . ?
C8 C9 C26 C27 80.6(6) . . . . ?
N3 C9 C26 C25 -40.2(5) . . . . ?
C8 C9 C26 C25 -157.4(4) . . . . ?
C24 C25 C26 C28 149.9(5) . . . . ?
C10 C25 C26 C28 -85.1(5) . . . . ?
C24 C25 C26 C27 28.8(6) . . . . ?
C10 C25 C26 C27 153.7(4) . . . . ?
C24 C25 C26 C9 -93.6(5) . . . . ?
C10 C25 C26 C9 31.4(5) . . . . ?
C35 C29 C30 C31 1.2(9) . . . . ?
C29 C30 C31 C33 -2.8(9) . . . . ?
C29 C30 C31 O2 -179.9(5) . . . . ?
C30 C31 C33 C34 3.4(9) . . . . ?
O2 C31 C33 C34 -179.2(5) . . . . ?
C31 C33 C34 C35 -2.3(8) . . . . ?
C30 C29 C35 C34 -0.2(8) . . . . ?
C30 C29 C35 C36 -178.5(5) . . . . ?
C33 C34 C35 C29 0.7(8) . . . . ?
C33 C34 C35 C36 179.1(5) . . . . ?
C29 C35 C36 N4 24.8(8) . . . . ?
C34 C35 C36 N4 -153.5(5) . . . . ?
C29 C35 C36 C2 -155.2(5) . . . . ?
C34 C35 C36 C2 26.5(8) . . . . ?
C3 C2 C36 N4 -124.1(6) . . . . ?
C1 C2 C36 N4 -1.7(6) . . . . ?
C3 C2 C36 C35 55.8(7) . . . . ?
C1 C2 C36 C35 178.3(5) . . . . ?
O3 C1 N3 C9 -74.3(5) . . . . ?
C2 C1 N3 C9 43.5(6) . . . . ?
O3 C1 N3 C10 56.5(5) . . . . ?
C2 C1 N3 C10 174.3(4) . . . . ?
C8 C9 N3 C1 -65.9(5) . . . . ?
C26 C9 N3 C1 169.4(4) . . . . ?
C8 C9 N3 C10 160.2(4) . . . . ?
C26 C9 N3 C10 35.5(5) . . . . ?
C25 C10 N3 C1 -148.8(4) . . . . ?
C11 C10 N3 C1 88.7(5) . . . . ?
C25 C10 N3 C9 -15.8(5) . . . . ?
C11 C10 N3 C9 -138.4(4) . . . . ?
C35 C36 N4 O3 178.6(4) . . . . ?
C2 C36 N4 O3 -1.4(6) . . . . ?
C30 C31 O2 C32 -9.6(9) . . . . ?
C33 C31 O2 C32 173.2(5) . . . . ?
C36 N4 O3 C1 4.2(5) . . . . ?
N3 C1 O3 N4 117.1(4) . . . . ?
C2 C1 O3 N4 -5.1(5) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.052

