# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1912388'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H22 Cl N O4'
_chemical_formula_sum            'C35 H22 Cl N O4'
_chemical_formula_weight         555.98

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                   10.0137(14)
_cell_length_b                   11.9245(16)
_cell_length_c                   12.3604(17)
_cell_angle_alpha                80.619(4)
_cell_angle_beta                 82.259(4)
_cell_angle_gamma                67.699(4)
_cell_volume                     1343.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6387
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             576
_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    0.185
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.964
_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            18954
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         25.995
_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             5266
_reflns_number_gt                3443
_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)+(0.0463P)²+0.4371P] 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         5266
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.7184(2) -0.05808(18) 0.78288(16) 0.0401(5) Uani 1 1 d . . . . .
C2 C 0.7092(2) -0.11739(19) 0.89859(18) 0.0449(5) Uani 1 1 d . . . . .
C3 C 0.6882(2) -0.23155(19) 0.88888(18) 0.0439(5) Uani 1 1 d . . . . .
C4 C 0.6741(2) -0.3192(2) 0.9723(2) 0.0537(6) Uani 1 1 d . . . . .
H4 H 0.6793 -0.3121 1.0453 0.064 Uiso 1 1 calc R U . . .
C5 C 0.6522(3) -0.4179(2) 0.9442(2) 0.0600(6) Uani 1 1 d . . . . .
H5 H 0.6430 -0.4787 0.9989 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6439(3) -0.4273(2) 0.8363(2) 0.0619(7) Uani 1 1 d . . . . .
H6 H 0.6286 -0.4945 0.8195 0.074 Uiso 1 1 calc R U . . .
C7 C 0.6578(2) -0.3392(2) 0.7517(2) 0.0537(6) Uani 1 1 d . . . . .
H7 H 0.6521 -0.3468 0.6789 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6803(2) -0.23990(18) 0.77866(18) 0.0432(5) Uani 1 1 d . . . . .
C9 C 0.6976(2) -0.13056(18) 0.71136(17) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.6964(2) -0.08876(18) 0.60033(17) 0.0384(5) Uani 1 1 d . . . . .
C11 C 0.6740(2) -0.1396(2) 0.50417(18) 0.0451(5) Uani 1 1 d . . . . .
C12 C 0.6832(2) -0.0515(2) 0.40718(18) 0.0463(5) Uani 1 1 d . . . . .
C13 C 0.6711(2) -0.0565(2) 0.29807(19) 0.0586(7) Uani 1 1 d . . . . .
H13 H 0.6593 -0.1232 0.2766 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6769(3) 0.0400(3) 0.2222(2) 0.0647(7) Uani 1 1 d . . . . .
H14 H 0.6696 0.0386 0.1482 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6934(3) 0.1389(3) 0.2548(2) 0.0640(7) Uani 1 1 d . . . . .
H15 H 0.6944 0.2042 0.2025 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7088(2) 0.1435(2) 0.36405(19) 0.0551(6) Uani 1 1 d . . . . .
H16 H 0.7215 0.2101 0.3848 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7046(2) 0.0466(2) 0.44073(17) 0.0434(5) Uani 1 1 d . . . . .
C18 C 0.7146(2) 0.02334(18) 0.56173(16) 0.0389(5) Uani 1 1 d . . . . .
C19 C 0.6829(2) 0.19481(19) 0.88614(17) 0.0478(5) Uani 1 1 d . . . . .
H19 H 0.5849 0.2147 0.8793 0.057 Uiso 1 1 calc R U . . .
C20 C 0.7241(2) 0.24845(19) 0.95941(18) 0.0493(6) Uani 1 1 d . . . . .
H20 H 0.6547 0.3040 1.0020 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8678(3) 0.2195(2) 0.96911(17) 0.0486(6) Uani 1 1 d . . . . .
C22 C 0.9711(3) 0.1388(3) 0.9069(2) 0.0712(8) Uani 1 1 d . . . . .
H22 H 1.0689 0.1196 0.9138 0.085 Uiso 1 1 calc R U . . .
C23 C 0.9278(3) 0.0861(2) 0.8332(2) 0.0667(7) Uani 1 1 d . . . . .
H23 H 0.9976 0.0318 0.7897 0.080 Uiso 1 1 calc R U . . .
C24 C 0.7840(2) 0.11220(17) 0.82275(16) 0.0390(5) Uani 1 1 d . . . . .
C25 C 0.7433(2) 0.04865(17) 0.74537(16) 0.0377(5) Uani 1 1 d . . . . .
C26 C 0.7390(2) 0.09260(18) 0.63146(17) 0.0388(5) Uani 1 1 d . . . . .
C27 C 0.7634(2) 0.20923(18) 0.59241(16) 0.0402(5) Uani 1 1 d . . . . .
C28 C 0.9003(3) 0.2069(2) 0.5522(2) 0.0606(7) Uani 1 1 d . . . . .
H28 H 0.9751 0.1321 0.5453 0.073 Uiso 1 1 calc R U . . .
C29 C 0.9279(3) 0.3129(3) 0.5221(2) 0.0714(8) Uani 1 1 d . . . . .
H29 H 1.0206 0.3097 0.4959 0.086 Uiso 1 1 calc R U . . .
C30 C 0.8169(3) 0.4236(2) 0.5313(2) 0.0621(7) Uani 1 1 d . . . . .
H30 H 0.8351 0.4955 0.5120 0.075 Uiso 1 1 calc R U . . .
C31 C 0.6802(3) 0.4288(2) 0.56863(18) 0.0492(6) Uani 1 1 d . . . . .
H31 H 0.6056 0.5041 0.5734 0.059 Uiso 1 1 calc R U . . .
C32 C 0.6520(2) 0.32224(18) 0.59932(16) 0.0391(5) Uani 1 1 d . . . . .
C33 C 0.4090(2) 0.4115(2) 0.69259(19) 0.0510(6) Uani 1 1 d . . . . .
C34 C 0.1634(3) 0.4772(3) 0.7628(2) 0.0732(8) Uani 1 1 d . . . . .
H34A H 0.1355 0.5552 0.7167 0.088 Uiso 1 1 calc R U . . .
H34B H 0.1878 0.4883 0.8327 0.088 Uiso 1 1 calc R U . . .
C35 C 0.0452(4) 0.4321(4) 0.7801(4) 0.1405(17) Uani 1 1 d . . . . .
H35A H 0.0232 0.4200 0.7107 0.211 Uiso 1 1 calc R U . . .
H35B H -0.0388 0.4906 0.8138 0.211 Uiso 1 1 calc R U . . .
H35C H 0.0731 0.3560 0.8274 0.211 Uiso 1 1 calc R U . . .
Cl1 Cl 0.92142(8) 0.28498(7) 1.06370(6) 0.0781(2) Uani 1 1 d . . . . .
N1 N 0.51050(18) 0.32551(15) 0.63535(14) 0.0449(4) Uani 1 1 d . . . . .
H1 H 0.4870 0.2681 0.6196 0.054 Uiso 1 1 calc R U . . .
O1 O 0.7117(2) -0.07959(15) 0.98296(13) 0.0652(5) Uani 1 1 d . . . . .
O2 O 0.65005(18) -0.23226(15) 0.50440(13) 0.0627(5) Uani 1 1 d . . . . .
O3 O 0.4238(2) 0.49440(19) 0.72495(19) 0.0942(7) Uani 1 1 d . . . . .
O4 O 0.28647(17) 0.38807(14) 0.70991(13) 0.0595(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C25 1.384(3) . ?
C1 C9 1.417(3) . ?
C1 C2 1.496(3) . ?
C2 O1 1.208(2) . ?
C2 C3 1.480(3) . ?
C3 C4 1.377(3) . ?
C3 C8 1.397(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.484(3) . ?
C9 C10 1.382(3) . ?
C10 C18 1.415(3) . ?
C10 C11 1.497(3) . ?
C11 O2 1.216(3) . ?
C11 C12 1.477(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.399(3) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.486(3) . ?
C18 C26 1.388(3) . ?
C19 C20 1.375(3) . ?
C19 C24 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.364(3) . ?
C21 Cl1 1.747(2) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.493(3) . ?
C25 C26 1.420(3) . ?
C26 C27 1.495(3) . ?
C27 C28 1.384(3) . ?
C27 C32 1.393(3) . ?
C28 C29 1.378(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.367(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.387(3) . ?
C31 H31 0.9300 . ?
C32 N1 1.414(3) . ?
C33 O3 1.190(3) . ?
C33 O4 1.341(3) . ?
C33 N1 1.355(3) . ?
C34 O4 1.446(3) . ?
C34 C35 1.453(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 C1 C9 122.71(18) . . ?
C25 C1 C2 128.66(18) . . ?
C9 C1 C2 108.62(17) . . ?
O1 C2 C3 126.5(2) . . ?
O1 C2 C1 128.48(19) . . ?
C3 C2 C1 104.96(17) . . ?
C4 C3 C8 122.1(2) . . ?
C4 C3 C2 127.8(2) . . ?
C8 C3 C2 110.05(19) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 119.3(2) . . ?
C7 C8 C9 132.5(2) . . ?
C3 C8 C9 108.14(17) . . ?
C10 C9 C1 117.74(18) . . ?
C10 C9 C8 134.09(18) . . ?
C1 C9 C8 108.17(18) . . ?
C9 C10 C18 119.97(17) . . ?
C9 C10 C11 131.66(19) . . ?
C18 C10 C11 108.35(18) . . ?
O2 C11 C12 126.39(19) . . ?
O2 C11 C10 128.0(2) . . ?
C12 C11 C10 105.55(18) . . ?
C13 C12 C17 121.8(2) . . ?
C13 C12 C11 128.6(2) . . ?
C17 C12 C11 109.52(18) . . ?
C14 C13 C12 118.1(2) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 C18 132.0(2) . . ?
C12 C17 C18 108.37(19) . . ?
C26 C18 C10 122.24(18) . . ?
C26 C18 C17 129.58(19) . . ?
C10 C18 C17 108.17(17) . . ?
C20 C19 C24 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C24 C19 H19 119.4 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 121.1(2) . . ?
C20 C21 Cl1 119.81(17) . . ?
C22 C21 Cl1 119.12(18) . . ?
C21 C22 C23 118.8(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C19 118.16(19) . . ?
C23 C24 C25 119.19(18) . . ?
C19 C24 C25 122.64(19) . . ?
C1 C25 C26 119.28(17) . . ?
C1 C25 C24 120.19(18) . . ?
C26 C25 C24 120.41(17) . . ?
C18 C26 C25 117.93(18) . . ?
C18 C26 C27 123.36(18) . . ?
C25 C26 C27 118.70(17) . . ?
C28 C27 C32 118.4(2) . . ?
C28 C27 C26 120.18(19) . . ?
C32 C27 C26 121.40(18) . . ?
C29 C28 C27 121.4(2) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C28 119.3(2) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.3(2) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.0(2) . . ?
C31 C32 N1 121.29(19) . . ?
C27 C32 N1 118.71(18) . . ?
O3 C33 O4 124.1(2) . . ?
O3 C33 N1 126.6(2) . . ?
O4 C33 N1 109.32(19) . . ?
O4 C34 C35 107.8(3) . . ?
O4 C34 H34A 110.2 . . ?
C35 C34 H34A 110.2 . . ?
O4 C34 H34B 110.2 . . ?
C35 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 N1 C32 125.49(18) . . ?
C33 N1 H1 117.3 . . ?
C32 N1 H1 117.3 . . ?
C33 O4 C34 116.15(19) . . ?

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 2.38 3.088(2) 140.6 2_656

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.038

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

data_1e
_database_code_depnum_ccdc_archive 'CCDC 1912389'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H22 Br N O4'
_chemical_formula_sum            'C35 H22 Br N O4'
_chemical_formula_weight         600.44

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                   9.9903(7)
_cell_length_b                   12.0129(8)
_cell_length_c                   12.3878(8)
_cell_angle_alpha                80.372(2)
_cell_angle_beta                 82.962(2)
_cell_angle_gamma                68.265(2)
_cell_volume                     1358.56(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6662
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             612
_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    1.555
_shelx_estimated_absorpt_T_min   0.688
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.733
_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            19563
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5312
_reflns_number_gt                3456
_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)+(0.0381P)²+0.6500P] 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         5312
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.07143(4) 0.20918(3) -0.06882(3) 0.08141(16) Uani 1 1 d . . . . .
C1 C 0.2864(3) 0.4771(2) 0.4384(2) 0.0413(6) Uani 1 1 d . . . . .
C2 C 0.2962(3) 0.4546(2) 0.5590(2) 0.0457(6) Uani 1 1 d . . . . .
C3 C 0.2914(3) 0.3587(3) 0.6363(2) 0.0584(8) Uani 1 1 d . . . . .
H3 H 0.2788 0.2923 0.6160 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3058(3) 0.3643(3) 0.7458(2) 0.0676(9) Uani 1 1 d . . . . .
H4 H 0.3040 0.2999 0.7986 0.081 Uiso 1 1 calc R U . . .
C5 C 0.3226(3) 0.4624(3) 0.7777(3) 0.0685(9) Uani 1 1 d . . . . .
H5 H 0.3301 0.4640 0.8515 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3284(3) 0.5579(3) 0.7017(2) 0.0609(8) Uani 1 1 d . . . . .
H6 H 0.3397 0.6245 0.7228 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3169(3) 0.5524(2) 0.5927(2) 0.0486(7) Uani 1 1 d . . . . .
C8 C 0.3262(3) 0.6394(3) 0.4958(2) 0.0488(7) Uani 1 1 d . . . . .
C9 C 0.3049(3) 0.5886(2) 0.3993(2) 0.0411(6) Uani 1 1 d . . . . .
C10 C 0.3053(2) 0.6294(2) 0.2888(2) 0.0404(6) Uani 1 1 d . . . . .
C11 C 0.3228(3) 0.7382(2) 0.2214(2) 0.0447(6) Uani 1 1 d . . . . .
C12 C 0.3443(3) 0.8376(2) 0.2483(3) 0.0573(8) Uani 1 1 d . . . . .
H12 H 0.3488 0.8455 0.3210 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3589(3) 0.9254(3) 0.1635(3) 0.0651(9) Uani 1 1 d . . . . .
H13 H 0.3729 0.9927 0.1804 0.078 Uiso 1 1 calc R U . . .
C14 C 0.3532(3) 0.9149(3) 0.0555(3) 0.0621(8) Uani 1 1 d . . . . .
H14 H 0.3641 0.9745 0.0006 0.075 Uiso 1 1 calc R U . . .
C15 C 0.3315(3) 0.8165(2) 0.0280(2) 0.0558(7) Uani 1 1 d . . . . .
H15 H 0.3265 0.8094 -0.0449 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3173(3) 0.7294(2) 0.1108(2) 0.0459(6) Uani 1 1 d . . . . .
C17 C 0.2956(3) 0.6156(2) 0.1016(2) 0.0461(6) Uani 1 1 d . . . . .
C18 C 0.2845(3) 0.5572(2) 0.2171(2) 0.0402(6) Uani 1 1 d . . . . .
C19 C 0.3173(3) 0.3062(2) 0.1163(2) 0.0496(7) Uani 1 1 d . . . . .
H19 H 0.4152 0.2868 0.1235 0.059 Uiso 1 1 calc R U . . .
C20 C 0.2737(3) 0.2525(2) 0.0436(2) 0.0507(7) Uani 1 1 d . . . . .
H20 H 0.3420 0.1968 0.0023 0.061 Uiso 1 1 calc R U . . .
C21 C 0.1316(3) 0.2812(2) 0.0328(2) 0.0479(7) Uani 1 1 d . . . . .
C22 C 0.0288(3) 0.3619(3) 0.0928(3) 0.0719(9) Uani 1 1 d . . . . .
H22 H -0.0689 0.3812 0.0848 0.086 Uiso 1 1 calc R U . . .
C23 C 0.0737(3) 0.4145(3) 0.1660(3) 0.0665(9) Uani 1 1 d . . . . .
H23 H 0.0049 0.4690 0.2081 0.080 Uiso 1 1 calc R U . . .
C24 C 0.2169(3) 0.3882(2) 0.17770(19) 0.0394(6) Uani 1 1 d . . . . .
C25 C 0.2586(3) 0.4513(2) 0.2548(2) 0.0387(6) Uani 1 1 d . . . . .
C26 C 0.2621(2) 0.4081(2) 0.3686(2) 0.0397(6) Uani 1 1 d . . . . .
C27 C 0.2371(3) 0.2923(2) 0.4082(2) 0.0424(6) Uani 1 1 d . . . . .
C28 C 0.1005(3) 0.2937(3) 0.4477(3) 0.0634(8) Uani 1 1 d . . . . .
H28 H 0.0261 0.3673 0.4545 0.076 Uiso 1 1 calc R U . . .
C29 C 0.0729(4) 0.1877(3) 0.4773(3) 0.0755(9) Uani 1 1 d . . . . .
H29 H -0.0193 0.1902 0.5035 0.091 Uiso 1 1 calc R U . . .
C30 C 0.1818(4) 0.0792(3) 0.4680(3) 0.0657(8) Uani 1 1 d . . . . .
H30 H 0.1630 0.0079 0.4868 0.079 Uiso 1 1 calc R U . . .
C31 C 0.3184(3) 0.0745(2) 0.4313(2) 0.0529(7) Uani 1 1 d . . . . .
H31 H 0.3922 0.0000 0.4266 0.063 Uiso 1 1 calc R U . . .
C32 C 0.3477(3) 0.1806(2) 0.40110(19) 0.0420(6) Uani 1 1 d . . . . .
C33 C 0.5892(3) 0.0947(3) 0.3087(2) 0.0538(7) Uani 1 1 d . . . . .
C34 C 0.8334(4) 0.0302(3) 0.2406(3) 0.0767(10) Uani 1 1 d . . . . .
H34A H 0.8580 -0.0485 0.2846 0.092 Uiso 1 1 calc R U . . .
H34B H 0.8089 0.0233 0.1692 0.092 Uiso 1 1 calc R U . . .
C35 C 0.9540(5) 0.0703(5) 0.2283(4) 0.146(2) Uani 1 1 d . . . . .
H35A H 0.9297 0.1473 0.1831 0.219 Uiso 1 1 calc R U . . .
H35B H 1.0361 0.0125 0.1946 0.219 Uiso 1 1 calc R U . . .
H35C H 0.9767 0.0780 0.2992 0.219 Uiso 1 1 calc R U . . .
N1 N 0.4885(2) 0.17805(18) 0.36623(17) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.5126 0.2344 0.3829 0.056 Uiso 1 1 calc R U . . .
O1 O 0.2944(2) 0.57808(18) 0.01737(15) 0.0666(6) Uani 1 1 d . . . . .
O2 O 0.3507(2) 0.73162(19) 0.49488(16) 0.0666(6) Uani 1 1 d . . . . .
O3 O 0.5718(2) 0.0140(2) 0.2744(2) 0.0979(9) Uani 1 1 d . . . . .
O4 O 0.7119(2) 0.11701(17) 0.29346(16) 0.0618(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
Br1 C21 1.905(2) . ?
C1 C26 1.390(3) . ?
C1 C9 1.417(3) . ?
C1 C2 1.482(3) . ?
C2 C3 1.381(4) . ?
C2 C7 1.401(4) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.472(4) . ?
C8 O2 1.217(3) . ?
C8 C9 1.501(3) . ?
C9 C10 1.375(3) . ?
C10 C18 1.422(3) . ?
C10 C11 1.485(4) . ?
C11 C12 1.386(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.485(3) . ?
C17 O1 1.207(3) . ?
C17 C18 1.495(4) . ?
C18 C25 1.385(3) . ?
C19 C24 1.374(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.349(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.495(3) . ?
C25 C26 1.419(3) . ?
C26 C27 1.495(3) . ?
C27 C28 1.387(4) . ?
C27 C32 1.396(3) . ?
C28 C29 1.383(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.365(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.392(4) . ?
C31 H31 0.9300 . ?
C32 N1 1.411(3) . ?
C33 O3 1.197(3) . ?
C33 O4 1.334(3) . ?
C33 N1 1.356(3) . ?
C34 C35 1.438(5) . ?
C34 O4 1.444(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 C1 C9 122.0(2) . . ?
C26 C1 C2 129.9(2) . . ?
C9 C1 C2 108.1(2) . . ?
C3 C2 C7 119.1(2) . . ?
C3 C2 C1 132.1(2) . . ?
C7 C2 C1 108.7(2) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C2 122.1(3) . . ?
C6 C7 C8 128.6(3) . . ?
C2 C7 C8 109.2(2) . . ?
O2 C8 C7 126.6(2) . . ?
O2 C8 C9 127.5(3) . . ?
C7 C8 C9 105.9(2) . . ?
C10 C9 C1 120.2(2) . . ?
C10 C9 C8 131.8(2) . . ?
C1 C9 C8 108.1(2) . . ?
C9 C10 C18 117.7(2) . . ?
C9 C10 C11 134.1(2) . . ?
C18 C10 C11 108.1(2) . . ?
C12 C11 C16 119.1(3) . . ?
C12 C11 C10 132.6(2) . . ?
C16 C11 C10 108.3(2) . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C11 122.1(2) . . ?
C15 C16 C17 128.2(2) . . ?
C11 C16 C17 109.7(2) . . ?
O1 C17 C16 126.0(3) . . ?
O1 C17 C18 128.6(2) . . ?
C16 C17 C18 105.2(2) . . ?
C25 C18 C10 122.6(2) . . ?
C25 C18 C17 128.8(2) . . ?
C10 C18 C17 108.5(2) . . ?
C24 C19 C20 120.4(2) . . ?
C24 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 121.4(2) . . ?
C20 C21 Br1 119.78(19) . . ?
C22 C21 Br1 118.8(2) . . ?
C21 C22 C23 118.4(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C19 118.6(2) . . ?
C23 C24 C25 119.0(2) . . ?
C19 C24 C25 122.4(2) . . ?
C18 C25 C26 119.2(2) . . ?
C18 C25 C24 120.4(2) . . ?
C26 C25 C24 120.3(2) . . ?
C1 C26 C25 118.0(2) . . ?
C1 C26 C27 123.1(2) . . ?
C25 C26 C27 118.8(2) . . ?
C28 C27 C32 118.3(2) . . ?
C28 C27 C26 120.4(2) . . ?
C32 C27 C26 121.2(2) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 119.7(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C32 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 119.9(2) . . ?
C31 C32 N1 121.4(2) . . ?
C27 C32 N1 118.7(2) . . ?
O3 C33 O4 124.3(3) . . ?
O3 C33 N1 125.9(3) . . ?
O4 C33 N1 109.9(2) . . ?
C35 C34 O4 108.7(3) . . ?
C35 C34 H34A 110.0 . . ?
O4 C34 H34A 110.0 . . ?
C35 C34 H34B 110.0 . . ?
O4 C34 H34B 110.0 . . ?
H34A C34 H34B 108.3 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 N1 C32 125.9(2) . . ?
C33 N1 H1 117.1 . . ?
C32 N1 H1 117.1 . . ?
C33 O4 C34 116.4(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
C26 C1 C2 C3 3.5(4) . . . . ?
C9 C1 C2 C3 -177.2(3) . . . . ?
C26 C1 C2 C7 -177.9(2) . . . . ?
C9 C1 C2 C7 1.4(3) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C2 1.6(4) . . . . ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C3 C2 C7 C6 -2.0(4) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
C3 C2 C7 C8 176.9(2) . . . . ?
C1 C2 C7 C8 -1.9(3) . . . . ?
C6 C7 C8 O2 2.5(4) . . . . ?
C2 C7 C8 O2 -176.3(3) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C2 C7 C8 C9 1.7(3) . . . . ?
C26 C1 C9 C10 -2.8(4) . . . . ?
C2 C1 C9 C10 177.9(2) . . . . ?
C26 C1 C9 C8 179.1(2) . . . . ?
C2 C1 C9 C8 -0.3(3) . . . . ?
O2 C8 C9 C10 -0.7(4) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
O2 C8 C9 C1 177.1(3) . . . . ?
C7 C8 C9 C1 -0.8(3) . . . . ?
C1 C9 C10 C18 0.9(3) . . . . ?
C8 C9 C10 C18 178.6(2) . . . . ?
C1 C9 C10 C11 -179.3(2) . . . . ?
C8 C9 C10 C11 -1.7(5) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C18 C10 C11 C12 179.3(3) . . . . ?
C9 C10 C11 C16 178.4(3) . . . . ?
C18 C10 C11 C16 -1.8(3) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C10 C11 C12 C13 179.1(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C11 0.6(4) . . . . ?
C14 C15 C16 C17 -179.0(3) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C10 C11 C16 C15 -179.5(2) . . . . ?
C12 C11 C16 C17 179.2(2) . . . . ?
C10 C11 C16 C17 0.2(3) . . . . ?
C15 C16 C17 O1 4.1(5) . . . . ?
C11 C16 C17 O1 -175.5(3) . . . . ?
C15 C16 C17 C18 -178.9(3) . . . . ?
C11 C16 C17 C18 1.5(3) . . . . ?
C9 C10 C18 C25 2.6(4) . . . . ?
C11 C10 C18 C25 -177.2(2) . . . . ?
C9 C10 C18 C17 -177.5(2) . . . . ?
C11 C10 C18 C17 2.7(3) . . . . ?
O1 C17 C18 C25 -5.8(4) . . . . ?
C16 C17 C18 C25 177.4(2) . . . . ?
O1 C17 C18 C10 174.3(3) . . . . ?
C16 C17 C18 C10 -2.6(3) . . . . ?
C24 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C19 C20 C21 Br1 179.0(2) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
Br1 C21 C22 C23 -179.5(3) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C22 C23 C24 C19 -1.0(5) . . . . ?
C22 C23 C24 C25 177.7(3) . . . . ?
C20 C19 C24 C23 0.5(4) . . . . ?
C20 C19 C24 C25 -178.2(2) . . . . ?
C10 C18 C25 C26 -4.3(3) . . . . ?
C17 C18 C25 C26 175.8(2) . . . . ?
C10 C18 C25 C24 171.3(2) . . . . ?
C17 C18 C25 C24 -8.7(4) . . . . ?
C23 C24 C25 C18 -92.3(3) . . . . ?
C19 C24 C25 C18 86.3(3) . . . . ?
C23 C24 C25 C26 83.2(3) . . . . ?
C19 C24 C25 C26 -98.2(3) . . . . ?
C9 C1 C26 C25 1.1(3) . . . . ?
C2 C1 C26 C25 -179.7(2) . . . . ?
C9 C1 C26 C27 -177.8(2) . . . . ?
C2 C1 C26 C27 1.4(4) . . . . ?
C18 C25 C26 C1 2.3(3) . . . . ?
C24 C25 C26 C1 -173.2(2) . . . . ?
C18 C25 C26 C27 -178.7(2) . . . . ?
C24 C25 C26 C27 5.7(3) . . . . ?
C1 C26 C27 C28 83.3(3) . . . . ?
C25 C26 C27 C28 -95.6(3) . . . . ?
C1 C26 C27 C32 -100.1(3) . . . . ?
C25 C26 C27 C32 81.0(3) . . . . ?
C32 C27 C28 C29 -1.4(4) . . . . ?
C26 C27 C28 C29 175.3(3) . . . . ?
C27 C28 C29 C30 0.2(5) . . . . ?
C28 C29 C30 C31 1.1(5) . . . . ?
C29 C30 C31 C32 -1.2(4) . . . . ?
C30 C31 C32 C27 0.0(4) . . . . ?
C30 C31 C32 N1 178.0(2) . . . . ?
C28 C27 C32 C31 1.3(4) . . . . ?
C26 C27 C32 C31 -175.4(2) . . . . ?
C28 C27 C32 N1 -176.8(2) . . . . ?
C26 C27 C32 N1 6.5(3) . . . . ?
O3 C33 N1 C32 3.7(5) . . . . ?
O4 C33 N1 C32 -177.5(2) . . . . ?
C31 C32 N1 C33 33.7(4) . . . . ?
C27 C32 N1 C33 -148.2(2) . . . . ?
O3 C33 O4 C34 -5.8(4) . . . . ?
N1 C33 O4 C34 175.4(2) . . . . ?
C35 C34 O4 C33 178.4(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 2.33 3.051(3) 141.1 2_666

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.045

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

data_3b
_database_code_depnum_ccdc_archive 'CCDC 1912393'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 Br N2 O3'
_chemical_formula_sum            'C37 H27 Br N2 O3'
_chemical_formula_weight         627.51

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

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

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

_cell_length_a                   11.5199(16)
_cell_length_b                   11.9192(18)
_cell_length_c                   12.6746(19)
_cell_angle_alpha                109.822(4)
_cell_angle_beta                 108.543(4)
_cell_angle_gamma                99.910(4)
_cell_volume                     1473.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2512
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             644
_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    1.436
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  0.750
_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            21139
_diffrn_reflns_av_unetI/netI     0.2105
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.913
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5774
_reflns_number_gt                2307
_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)+(0.0350P)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         5774
_refine_ls_number_parameters     410
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.2440
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.005
_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 0.86799(7) -0.14335(7) 0.31934(7) 0.1049(3) Uani 1 1 d . . . . .
C1 C 0.6174(4) 0.4435(4) 0.6488(4) 0.0363(12) Uani 1 1 d . . . . .
C2 C 0.6691(5) 0.5669(4) 0.7574(4) 0.0385(12) Uani 1 1 d . . . . .
C3 C 0.7904(5) 0.6352(5) 0.8495(5) 0.0485(14) Uani 1 1 d . . . . .
H3 H 0.8603 0.6063 0.8489 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8067(5) 0.7473(5) 0.9427(5) 0.0608(15) Uani 1 1 d . . . . .
H4 H 0.8883 0.7934 1.0050 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7047(5) 0.7919(5) 0.9450(5) 0.0644(16) Uani 1 1 d . . . . .
H5 H 0.7179 0.8668 1.0093 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5826(5) 0.7265(5) 0.8526(5) 0.0545(14) Uani 1 1 d . . . . .
H6 H 0.5137 0.7572 0.8525 0.065 Uiso 1 1 calc R U . . .
C7 C 0.5663(4) 0.6144(5) 0.7606(4) 0.0418(13) Uani 1 1 d . . . . .
C8 C 0.4459(5) 0.5260(5) 0.6542(4) 0.0434(13) Uani 1 1 d . . . . .
C9 C 0.4823(4) 0.4182(4) 0.5857(4) 0.0373(12) Uani 1 1 d . . . . .
C10 C 0.4118(4) 0.3075(5) 0.4825(4) 0.0389(12) Uani 1 1 d . . . . .
C11 C 0.2726(4) 0.2514(5) 0.3982(4) 0.0437(13) Uani 1 1 d . . . . .
C12 C 0.1678(5) 0.2944(5) 0.3967(5) 0.0631(16) Uani 1 1 d . . . . .
H12 H 0.1778 0.3713 0.4565 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0481(5) 0.2200(7) 0.3039(6) 0.088(2) Uani 1 1 d . . . . .
H13 H -0.0229 0.2478 0.3016 0.105 Uiso 1 1 calc R U . . .
C14 C 0.0316(5) 0.1053(7) 0.2145(6) 0.093(2) Uani 1 1 d . . . . .
H14 H -0.0498 0.0577 0.1525 0.112 Uiso 1 1 calc R U . . .
C15 C 0.1348(5) 0.0608(5) 0.2164(5) 0.0704(17) Uani 1 1 d . . . . .
H15 H 0.1243 -0.0167 0.1573 0.085 Uiso 1 1 calc R U . . .
C16 C 0.2537(5) 0.1353(5) 0.3088(5) 0.0490(14) Uani 1 1 d . . . . .
C17 C 0.3790(5) 0.1084(5) 0.3322(5) 0.0499(14) Uani 1 1 d . . . . .
C18 C 0.4763(4) 0.2225(4) 0.4418(4) 0.0391(12) Uani 1 1 d . . . . .
C19 C 0.7122(5) 0.0830(5) 0.5215(5) 0.0662(16) Uani 1 1 d . . . . .
H19 H 0.6999 0.0945 0.5931 0.079 Uiso 1 1 calc R U . . .
C20 C 0.7723(6) -0.0039(5) 0.4804(6) 0.0764(18) Uani 1 1 d . . . . .
H20 H 0.8011 -0.0492 0.5246 0.092 Uiso 1 1 calc R U . . .
C21 C 0.7886(5) -0.0218(5) 0.3752(5) 0.0595(15) Uani 1 1 d . . . . .
C22 C 0.7507(5) 0.0461(5) 0.3121(5) 0.0696(17) Uani 1 1 d . . . . .
H22 H 0.7639 0.0345 0.2410 0.084 Uiso 1 1 calc R U . . .
C23 C 0.6922(5) 0.1328(5) 0.3543(5) 0.0627(16) Uani 1 1 d . . . . .
H23 H 0.6666 0.1798 0.3108 0.075 Uiso 1 1 calc R U . . .
C24 C 0.6707(4) 0.1518(4) 0.4586(4) 0.0384(12) Uani 1 1 d . . . . .
C25 C 0.6074(4) 0.2455(4) 0.5026(4) 0.0383(12) Uani 1 1 d . . . . .
C26 C 0.6812(4) 0.3599(4) 0.6091(4) 0.0368(12) Uani 1 1 d . . . . .
C27 C 0.8231(4) 0.3850(4) 0.6738(5) 0.0385(12) Uani 1 1 d . . . . .
C28 C 0.9044(5) 0.4190(4) 0.6218(5) 0.0496(14) Uani 1 1 d . . . . .
H28 H 0.8704 0.4275 0.5489 0.060 Uiso 1 1 calc R U . . .
C29 C 1.0360(5) 0.4405(5) 0.6773(6) 0.0640(16) Uani 1 1 d . . . . .
H29 H 1.0907 0.4634 0.6425 0.077 Uiso 1 1 calc R U . . .
C30 C 1.0835(5) 0.4271(5) 0.7846(6) 0.0633(16) Uani 1 1 d . . . . .
H30 H 1.1718 0.4422 0.8225 0.076 Uiso 1 1 calc R U . . .
C31 C 1.0066(5) 0.3925(5) 0.8384(5) 0.0551(15) Uani 1 1 d . . . . .
H31 H 1.0418 0.3840 0.9111 0.066 Uiso 1 1 calc R U . . .
C32 C 0.8735(4) 0.3702(4) 0.7817(5) 0.0415(13) Uani 1 1 d . . . . .
C33 C 0.8047(5) 0.2944(5) 0.9218(5) 0.0505(14) Uani 1 1 d . . . . .
C34 C 0.7217(6) 0.2436(6) 1.0592(6) 0.0924(18) Uani 1 1 d . U . . .
H34A H 0.8126 0.2587 1.1046 0.111 Uiso 1 1 calc R U . . .
H34B H 0.6908 0.2946 1.1150 0.111 Uiso 1 1 calc R U . . .
C35 C 0.6534(7) 0.1143(6) 1.0168(6) 0.111(2) Uani 1 1 d . U . . .
H35A H 0.5642 0.0977 0.9676 0.166 Uiso 1 1 calc R U . . .
H35B H 0.6602 0.0952 1.0859 0.166 Uiso 1 1 calc R U . . .
H35C H 0.6896 0.0630 0.9684 0.166 Uiso 1 1 calc R U . . .
C36 C 0.5692(9) 0.2665(11) 0.8816(12) 0.082(3) Uani 0.496(7) 1 d D U P A 1
H36A H 0.5112 0.2067 0.8929 0.099 Uiso 0.496(7) 1 calc R U P A 1
H36B H 0.5542 0.2327 0.7955 0.099 Uiso 0.496(7) 1 calc R U P A 1
C37 C 0.5401(11) 0.3906(10) 0.9170(12) 0.087(3) Uani 0.496(7) 1 d D U P A 1
H37A H 0.5506 0.4220 1.0011 0.131 Uiso 0.496(7) 1 calc R U P A 1
H37B H 0.4530 0.3778 0.8651 0.131 Uiso 0.496(7) 1 calc R U P A 1
H37C H 0.5984 0.4503 0.9072 0.131 Uiso 0.496(7) 1 calc R U P A 1
C36' C 0.6135(10) 0.3530(11) 0.9426(11) 0.084(3) Uani 0.504(7) 1 d D U P A 2
H36C H 0.6520 0.4310 0.9409 0.100 Uiso 0.504(7) 1 calc R U P A 2
H36D H 0.5858 0.3722 1.0096 0.100 Uiso 0.504(7) 1 calc R U P A 2
C37' C 0.5004(11) 0.2680(12) 0.8215(10) 0.089(3) Uani 0.504(7) 1 d D U P A 2
H37D H 0.5294 0.2501 0.7563 0.134 Uiso 0.504(7) 1 calc R U P A 2
H37E H 0.4361 0.3092 0.8071 0.134 Uiso 0.504(7) 1 calc R U P A 2
H37F H 0.4639 0.1910 0.8245 0.134 Uiso 0.504(7) 1 calc R U P A 2
N1 N 0.7872(4) 0.3379(4) 0.8311(4) 0.0554(12) Uani 1 1 d . . . . .
H1 H 0.7126 0.3461 0.8009 0.066 Uiso 1 1 calc R U . . .
N2 N 0.7065(4) 0.2827(4) 0.9577(4) 0.0735(13) Uani 1 1 d D U . . .
O1 O 0.3388(3) 0.5398(3) 0.6294(3) 0.0629(10) Uani 1 1 d . . . . .
O2 O 0.3961(3) 0.0126(4) 0.2762(3) 0.0721(11) Uani 1 1 d . . . . .
O3 O 0.9010(3) 0.2677(4) 0.9640(3) 0.0752(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
Br1 C21 1.900(5) . ?
C1 C26 1.391(6) . ?
C1 C9 1.427(6) . ?
C1 C2 1.489(6) . ?
C2 C3 1.380(6) . ?
C2 C7 1.403(6) . ?
C3 C4 1.385(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.482(6) . ?
C8 O1 1.228(5) . ?
C8 C9 1.496(6) . ?
C9 C10 1.378(6) . ?
C10 C18 1.412(6) . ?
C10 C11 1.489(6) . ?
C11 C16 1.387(6) . ?
C11 C12 1.388(6) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.492(6) . ?
C17 O2 1.210(5) . ?
C17 C18 1.496(6) . ?
C18 C25 1.387(6) . ?
C19 C24 1.369(6) . ?
C19 C20 1.391(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.350(7) . ?
C22 C23 1.379(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.486(6) . ?
C25 C26 1.424(6) . ?
C26 C27 1.499(6) . ?
C27 C28 1.385(6) . ?
C27 C32 1.391(6) . ?
C28 C29 1.387(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.371(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.366(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.402(6) . ?
C31 H31 0.9300 . ?
C32 N1 1.400(6) . ?
C33 O3 1.216(5) . ?
C33 N2 1.350(6) . ?
C33 N1 1.386(6) . ?
C34 C35 1.427(8) . ?
C34 N2 1.481(6) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 N2 1.506(8) . ?
C36 C37 1.523(9) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C36' N2 1.474(8) . ?
C36' C37' 1.516(9) . ?
C36' H36C 0.9700 . ?
C36' H36D 0.9700 . ?
C37' H37D 0.9600 . ?
C37' H37E 0.9600 . ?
C37' H37F 0.9600 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 C1 C9 122.1(4) . . ?
C26 C1 C2 129.4(4) . . ?
C9 C1 C2 108.5(4) . . ?
C3 C2 C7 118.7(4) . . ?
C3 C2 C1 133.1(4) . . ?
C7 C2 C1 108.2(4) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.0(4) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 122.2(4) . . ?
C6 C7 C8 128.3(4) . . ?
C2 C7 C8 109.5(4) . . ?
O1 C8 C7 126.1(4) . . ?
O1 C8 C9 127.9(5) . . ?
C7 C8 C9 106.0(4) . . ?
C10 C9 C1 119.4(4) . . ?
C10 C9 C8 132.7(4) . . ?
C1 C9 C8 107.8(4) . . ?
C9 C10 C18 118.6(4) . . ?
C9 C10 C11 133.3(4) . . ?
C18 C10 C11 108.1(4) . . ?
C16 C11 C12 119.3(4) . . ?
C16 C11 C10 108.9(4) . . ?
C12 C11 C10 131.8(5) . . ?
C13 C12 C11 118.2(5) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C14 121.6(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 117.7(5) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C11 122.6(5) . . ?
C15 C16 C17 128.2(5) . . ?
C11 C16 C17 109.2(4) . . ?
O2 C17 C16 126.7(5) . . ?
O2 C17 C18 127.9(5) . . ?
C16 C17 C18 105.3(4) . . ?
C25 C18 C10 122.6(4) . . ?
C25 C18 C17 128.9(4) . . ?
C10 C18 C17 108.5(4) . . ?
C24 C19 C20 121.1(5) . . ?
C24 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.4(5) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 120.9(5) . . ?
C22 C21 Br1 120.6(4) . . ?
C20 C21 Br1 118.5(5) . . ?
C21 C22 C23 119.3(5) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.8(5) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C19 C24 C23 117.5(4) . . ?
C19 C24 C25 121.4(4) . . ?
C23 C24 C25 121.1(4) . . ?
C18 C25 C26 119.2(4) . . ?
C18 C25 C24 120.8(4) . . ?
C26 C25 C24 120.0(4) . . ?
C1 C26 C25 118.0(4) . . ?
C1 C26 C27 122.9(4) . . ?
C25 C26 C27 119.1(4) . . ?
C28 C27 C32 119.6(4) . . ?
C28 C27 C26 118.9(5) . . ?
C32 C27 C26 121.4(4) . . ?
C27 C28 C29 120.8(5) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 118.3(5) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C31 C30 C29 122.8(5) . . ?
C31 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
C30 C31 C32 118.7(5) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C27 C32 N1 117.2(4) . . ?
C27 C32 C31 119.7(5) . . ?
N1 C32 C31 123.1(5) . . ?
O3 C33 N2 123.1(5) . . ?
O3 C33 N1 121.9(5) . . ?
N2 C33 N1 115.0(5) . . ?
C35 C34 N2 112.6(6) . . ?
C35 C34 H34A 109.1 . . ?
N2 C34 H34A 109.1 . . ?
C35 C34 H34B 109.1 . . ?
N2 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N2 C36 C37 111.4(9) . . ?
N2 C36 H36A 109.3 . . ?
C37 C36 H36A 109.3 . . ?
N2 C36 H36B 109.3 . . ?
C37 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N2 C36' C37' 105.9(8) . . ?
N2 C36' H36C 110.6 . . ?
C37' C36' H36C 110.6 . . ?
N2 C36' H36D 110.6 . . ?
C37' C36' H36D 110.6 . . ?
H36C C36' H36D 108.7 . . ?
C36' C37' H37D 109.5 . . ?
C36' C37' H37E 109.5 . . ?
H37D C37' H37E 109.5 . . ?
C36' C37' H37F 109.5 . . ?
H37D C37' H37F 109.5 . . ?
H37E C37' H37F 109.5 . . ?
C33 N1 C32 129.2(4) . . ?
C33 N1 H1 115.4 . . ?
C32 N1 H1 115.4 . . ?
C33 N2 C36' 123.3(7) . . ?
C33 N2 C34 117.9(5) . . ?
C36' N2 C34 113.8(7) . . ?
C33 N2 C36 125.0(7) . . ?
C34 N2 C36 114.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C26 C1 C2 C3 -0.1(9) . . . . ?
C9 C1 C2 C3 179.0(5) . . . . ?
C26 C1 C2 C7 -178.3(5) . . . . ?
C9 C1 C2 C7 0.8(5) . . . . ?
C7 C2 C3 C4 0.8(7) . . . . ?
C1 C2 C3 C4 -177.3(5) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C4 C5 C6 C7 1.7(8) . . . . ?
C5 C6 C7 C2 -1.1(8) . . . . ?
C5 C6 C7 C8 178.3(5) . . . . ?
C3 C2 C7 C6 -0.1(7) . . . . ?
C1 C2 C7 C6 178.4(4) . . . . ?
C3 C2 C7 C8 -179.6(4) . . . . ?
C1 C2 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 O1 1.0(8) . . . . ?
C2 C7 C8 O1 -179.5(5) . . . . ?
C6 C7 C8 C9 -178.5(5) . . . . ?
C2 C7 C8 C9 1.0(5) . . . . ?
C26 C1 C9 C10 0.4(7) . . . . ?
C2 C1 C9 C10 -178.8(4) . . . . ?
C26 C1 C9 C8 179.0(4) . . . . ?
C2 C1 C9 C8 -0.1(5) . . . . ?
O1 C8 C9 C10 -1.6(9) . . . . ?
C7 C8 C9 C10 177.9(5) . . . . ?
O1 C8 C9 C1 180.0(5) . . . . ?
C7 C8 C9 C1 -0.5(5) . . . . ?
C1 C9 C10 C18 -0.5(6) . . . . ?
C8 C9 C10 C18 -178.8(5) . . . . ?
C1 C9 C10 C11 178.6(4) . . . . ?
C8 C9 C10 C11 0.4(9) . . . . ?
C9 C10 C11 C16 -179.2(5) . . . . ?
C18 C10 C11 C16 0.0(5) . . . . ?
C9 C10 C11 C12 0.4(9) . . . . ?
C18 C10 C11 C12 179.6(5) . . . . ?
C16 C11 C12 C13 -1.1(8) . . . . ?
C10 C11 C12 C13 179.3(5) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
C12 C13 C14 C15 0.8(10) . . . . ?
C13 C14 C15 C16 -0.9(10) . . . . ?
C14 C15 C16 C11 0.0(8) . . . . ?
C14 C15 C16 C17 179.1(5) . . . . ?
C12 C11 C16 C15 1.1(8) . . . . ?
C10 C11 C16 C15 -179.3(5) . . . . ?
C12 C11 C16 C17 -178.2(4) . . . . ?
C10 C11 C16 C17 1.4(5) . . . . ?
C15 C16 C17 O2 -3.7(9) . . . . ?
C11 C16 C17 O2 175.5(5) . . . . ?
C15 C16 C17 C18 178.5(5) . . . . ?
C11 C16 C17 C18 -2.3(5) . . . . ?
C9 C10 C18 C25 0.9(7) . . . . ?
C11 C10 C18 C25 -178.4(4) . . . . ?
C9 C10 C18 C17 177.9(4) . . . . ?
C11 C10 C18 C17 -1.5(5) . . . . ?
O2 C17 C18 C25 1.2(9) . . . . ?
C16 C17 C18 C25 178.9(5) . . . . ?
O2 C17 C18 C10 -175.5(5) . . . . ?
C16 C17 C18 C10 2.3(5) . . . . ?
C24 C19 C20 C21 -0.9(9) . . . . ?
C19 C20 C21 C22 2.0(9) . . . . ?
C19 C20 C21 Br1 -178.8(4) . . . . ?
C20 C21 C22 C23 -1.4(9) . . . . ?
Br1 C21 C22 C23 179.4(4) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C20 C19 C24 C23 -0.7(8) . . . . ?
C20 C19 C24 C25 -179.5(5) . . . . ?
C22 C23 C24 C19 1.4(8) . . . . ?
C22 C23 C24 C25 -179.9(5) . . . . ?
C10 C18 C25 C26 -1.2(7) . . . . ?
C17 C18 C25 C26 -177.4(4) . . . . ?
C10 C18 C25 C24 178.2(4) . . . . ?
C17 C18 C25 C24 1.9(7) . . . . ?
C19 C24 C25 C18 -108.2(6) . . . . ?
C23 C24 C25 C18 73.1(6) . . . . ?
C19 C24 C25 C26 71.1(6) . . . . ?
C23 C24 C25 C26 -107.5(5) . . . . ?
C9 C1 C26 C25 -0.6(7) . . . . ?
C2 C1 C26 C25 178.4(4) . . . . ?
C9 C1 C26 C27 179.7(4) . . . . ?
C2 C1 C26 C27 -1.3(8) . . . . ?
C18 C25 C26 C1 1.0(6) . . . . ?
C24 C25 C26 C1 -178.4(4) . . . . ?
C18 C25 C26 C27 -179.4(4) . . . . ?
C24 C25 C26 C27 1.3(6) . . . . ?
C1 C26 C27 C28 -105.2(5) . . . . ?
C25 C26 C27 C28 75.1(6) . . . . ?
C1 C26 C27 C32 77.3(6) . . . . ?
C25 C26 C27 C32 -102.4(5) . . . . ?
C32 C27 C28 C29 -1.1(7) . . . . ?
C26 C27 C28 C29 -178.6(4) . . . . ?
C27 C28 C29 C30 0.1(7) . . . . ?
C28 C29 C30 C31 0.6(8) . . . . ?
C29 C30 C31 C32 -0.3(8) . . . . ?
C28 C27 C32 N1 179.0(4) . . . . ?
C26 C27 C32 N1 -3.6(6) . . . . ?
C28 C27 C32 C31 1.4(7) . . . . ?
C26 C27 C32 C31 178.9(4) . . . . ?
C30 C31 C32 C27 -0.8(7) . . . . ?
C30 C31 C32 N1 -178.1(5) . . . . ?
O3 C33 N1 C32 -6.9(8) . . . . ?
N2 C33 N1 C32 174.0(5) . . . . ?
C27 C32 N1 C33 166.4(5) . . . . ?
C31 C32 N1 C33 -16.2(8) . . . . ?
O3 C33 N2 C36' 157.8(7) . . . . ?
N1 C33 N2 C36' -23.1(9) . . . . ?
O3 C33 N2 C34 4.3(8) . . . . ?
N1 C33 N2 C34 -176.6(5) . . . . ?
O3 C33 N2 C36 -155.7(7) . . . . ?
N1 C33 N2 C36 23.4(9) . . . . ?
C37' C36' N2 C33 93.5(10) . . . . ?
C37' C36' N2 C34 -112.0(9) . . . . ?
C35 C34 N2 C33 -102.1(6) . . . . ?
C35 C34 N2 C36' 101.9(8) . . . . ?
C35 C34 N2 C36 60.0(8) . . . . ?
C37 C36 N2 C33 -98.3(11) . . . . ?
C37 C36 N2 C34 101.0(11) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1912391'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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         'C32 H18 Br N O2'
_chemical_formula_sum            'C32 H18 Br N O2'
_chemical_formula_weight         528.38

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                   12.5801(11)
_cell_length_b                   29.118(2)
_cell_length_c                   7.2563(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.229(3)
_cell_angle_gamma                90
_cell_volume                     2630.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3467
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      21.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.591
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.727
_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            24587
_diffrn_reflns_av_unetI/netI     0.1450
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.661
_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             5148
_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)+(0.0928P)²+2.8324P] 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         5148
_refine_ls_number_parameters     325
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2118
_refine_ls_wR_factor_gt          0.1713
_refine_ls_goodness_of_fit_ref   1.021
_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
Br1 Br 0.57373(7) -0.04388(2) 0.20094(12) 0.0835(4) Uani 1 1 d . . . . .
O1 O 0.5281(3) 0.15715(18) 0.2542(6) 0.0652(14) Uani 1 1 d . . . . .
O2 O 0.8890(3) 0.31429(11) 0.5911(5) 0.0345(9) Uani 1 1 d . . . . .
N1 N 0.9988(5) 0.10051(19) 0.3237(8) 0.0712(18) Uani 1 1 d . . . . .
H1A H 0.9597 0.1233 0.2796 0.085 Uiso 1 1 calc R U . . .
H1B H 1.0391 0.0866 0.2551 0.085 Uiso 1 1 calc R U . . .
C1 C 0.7040(4) 0.1841(2) 0.3991(7) 0.0341(13) Uani 1 1 d . U . . .
C2 C 0.5910(5) 0.1881(2) 0.3079(7) 0.0424(14) Uani 1 1 d . U . . .
C3 C 0.5688(4) 0.2382(2) 0.2948(7) 0.0439(14) Uani 1 1 d . U . . .
C4 C 0.4752(5) 0.2602(3) 0.2209(8) 0.0607(18) Uani 1 1 d . U . . .
H4 H 0.4152 0.2436 0.1686 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4735(5) 0.3078(3) 0.2269(9) 0.0680(19) Uani 1 1 d . U . . .
H5 H 0.4112 0.3234 0.1790 0.082 Uiso 1 1 calc R U . . .
C6 C 0.5629(5) 0.3321(3) 0.3029(9) 0.0574(17) Uani 1 1 d . U . . .
H6 H 0.5601 0.3641 0.3045 0.069 Uiso 1 1 calc R U . . .
C7 C 0.6581(4) 0.3097(2) 0.3782(8) 0.0443(14) Uani 1 1 d . U . . .
H7 H 0.7182 0.3264 0.4290 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6603(4) 0.2623(2) 0.3750(7) 0.0361(13) Uani 1 1 d . U . . .
C9 C 0.7443(4) 0.22899(18) 0.4426(6) 0.0284(12) Uani 1 1 d . U . . .
C10 C 0.8481(4) 0.23293(16) 0.5390(6) 0.0249(11) Uani 1 1 d . U . . .
C11 C 0.9139(4) 0.27391(16) 0.6062(7) 0.0242(11) Uani 1 1 d . U . . .
C12 C 1.0182(4) 0.25520(16) 0.6970(7) 0.0255(11) Uani 1 1 d . U . . .
C13 C 1.1090(4) 0.27880(18) 0.7772(7) 0.0329(12) Uani 1 1 d . U . . .
H13 H 1.1095 0.3107 0.7812 0.040 Uiso 1 1 calc R U . . .
C14 C 1.1972(4) 0.2542(2) 0.8499(7) 0.0376(13) Uani 1 1 d . U . . .
H14 H 1.2591 0.2695 0.9030 0.045 Uiso 1 1 calc R U . . .
C15 C 1.1952(4) 0.20642(19) 0.8449(7) 0.0382(13) Uani 1 1 d . U . . .
H15 H 1.2559 0.1902 0.8964 0.046 Uiso 1 1 calc R U . . .
C16 C 1.1053(4) 0.18256(19) 0.7655(7) 0.0350(13) Uani 1 1 d . U . . .
H16 H 1.1053 0.1506 0.7628 0.042 Uiso 1 1 calc R U . . .
C17 C 1.0148(4) 0.20713(16) 0.6899(7) 0.0259(11) Uani 1 1 d . U . . .
C18 C 0.9080(4) 0.19299(16) 0.5918(6) 0.0251(11) Uani 1 1 d . U . . .
C19 C 0.6859(7) 0.0684(3) 0.5174(11) 0.086(2) Uani 1 1 d . U . . .
H19 H 0.6919 0.0766 0.6423 0.104 Uiso 1 1 calc R U . . .
C20 C 0.6421(7) 0.0261(3) 0.4588(12) 0.094(2) Uani 1 1 d . U . . .
H20 H 0.6182 0.0063 0.5445 0.113 Uiso 1 1 calc R U . . .
C21 C 0.6343(6) 0.0136(2) 0.2767(10) 0.0594(17) Uani 1 1 d . U . . .
C22 C 0.6764(5) 0.0410(2) 0.1557(9) 0.0579(17) Uani 1 1 d . U . . .
H22 H 0.6763 0.0316 0.0332 0.069 Uiso 1 1 calc R U . . .
C23 C 0.7191(5) 0.0827(2) 0.2139(9) 0.0551(16) Uani 1 1 d . U . . .
H23 H 0.7484 0.1010 0.1289 0.066 Uiso 1 1 calc R U . . .
C24 C 0.7207(5) 0.09840(19) 0.3900(8) 0.0460(14) Uani 1 1 d . U . . .
C25 C 0.7648(4) 0.14468(18) 0.4481(7) 0.0343(13) Uani 1 1 d . U . . .
C26 C 0.8689(4) 0.14901(17) 0.5494(7) 0.0301(12) Uani 1 1 d . U . . .
C27 C 0.9341(5) 0.10794(17) 0.6108(8) 0.0413(14) Uani 1 1 d . U . . .
C28 C 0.9971(5) 0.0868(2) 0.4965(9) 0.0491(15) Uani 1 1 d . U . . .
C29 C 1.0633(6) 0.0492(2) 0.5679(11) 0.0698(19) Uani 1 1 d . U . . .
H29 H 1.1092 0.0353 0.4952 0.084 Uiso 1 1 calc R U . . .
C30 C 1.0583(8) 0.0340(3) 0.7433(12) 0.089(2) Uani 1 1 d . U . . .
H30 H 1.0993 0.0087 0.7872 0.107 Uiso 1 1 calc R U . . .
C31 C 0.9967(8) 0.0541(3) 0.8551(14) 0.100(2) Uani 1 1 d . U . . .
H31 H 0.9987 0.0433 0.9762 0.120 Uiso 1 1 calc R U . . .
C32 C 0.9297(6) 0.0906(2) 0.7943(10) 0.075(2) Uani 1 1 d . U . . .
H32 H 0.8837 0.1034 0.8700 0.090 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
Br1 C21 1.888(6) . ?
O1 C2 1.225(7) . ?
O2 C11 1.218(5) . ?
N1 C28 1.318(8) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C1 C25 1.397(7) . ?
C1 C9 1.422(7) . ?
C1 C2 1.485(8) . ?
C2 C3 1.486(9) . ?
C3 C4 1.380(8) . ?
C3 C8 1.402(8) . ?
C4 C5 1.386(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.466(7) . ?
C9 C10 1.394(7) . ?
C10 C18 1.409(7) . ?
C10 C11 1.494(7) . ?
C11 C12 1.484(7) . ?
C12 C13 1.387(7) . ?
C12 C17 1.401(7) . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.487(7) . ?
C18 C26 1.390(7) . ?
C19 C24 1.387(8) . ?
C19 C20 1.390(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.349(8) . ?
C22 C23 1.370(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.354(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.495(7) . ?
C25 C26 1.412(7) . ?
C26 C27 1.482(7) . ?
C27 C28 1.371(8) . ?
C27 C32 1.433(8) . ?
C28 C29 1.428(9) . ?
C29 C30 1.357(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.333(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.390(10) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

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
C28 N1 H1A 120.0 . . ?
C28 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C25 C1 C9 122.3(5) . . ?
C25 C1 C2 129.3(5) . . ?
C9 C1 C2 108.4(5) . . ?
O1 C2 C1 128.1(6) . . ?
O1 C2 C3 126.6(6) . . ?
C1 C2 C3 105.4(5) . . ?
C4 C3 C8 122.2(6) . . ?
C4 C3 C2 128.5(6) . . ?
C8 C3 C2 109.3(5) . . ?
C3 C4 C5 117.9(7) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 120.9(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.2(7) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.5(6) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C3 119.3(5) . . ?
C7 C8 C9 132.2(5) . . ?
C3 C8 C9 108.5(5) . . ?
C10 C9 C1 117.7(5) . . ?
C10 C9 C8 133.7(5) . . ?
C1 C9 C8 108.5(5) . . ?
C9 C10 C18 119.6(4) . . ?
C9 C10 C11 131.7(5) . . ?
C18 C10 C11 108.7(4) . . ?
O2 C11 C12 126.4(5) . . ?
O2 C11 C10 128.2(5) . . ?
C12 C11 C10 105.4(4) . . ?
C13 C12 C17 121.9(5) . . ?
C13 C12 C11 128.8(5) . . ?
C17 C12 C11 109.3(4) . . ?
C14 C13 C12 118.6(5) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 118.8(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 118.8(5) . . ?
C16 C17 C18 132.9(5) . . ?
C12 C17 C18 108.3(4) . . ?
C26 C18 C10 122.8(5) . . ?
C26 C18 C17 128.9(5) . . ?
C10 C18 C17 108.3(4) . . ?
C24 C19 C20 120.2(7) . . ?
C24 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.3(7) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 119.5(6) . . ?
C22 C21 Br1 120.9(5) . . ?
C20 C21 Br1 119.4(5) . . ?
C21 C22 C23 119.8(6) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 122.8(6) . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C23 C24 C19 116.9(6) . . ?
C23 C24 C25 121.7(5) . . ?
C19 C24 C25 121.3(5) . . ?
C1 C25 C26 119.5(5) . . ?
C1 C25 C24 120.0(5) . . ?
C26 C25 C24 120.4(5) . . ?
C18 C26 C25 118.0(5) . . ?
C18 C26 C27 120.9(5) . . ?
C25 C26 C27 121.1(4) . . ?
C28 C27 C32 120.5(6) . . ?
C28 C27 C26 121.5(5) . . ?
C32 C27 C26 118.0(5) . . ?
N1 C28 C27 122.0(6) . . ?
N1 C28 C29 119.3(6) . . ?
C27 C28 C29 118.8(6) . . ?
C30 C29 C28 119.2(7) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C31 C30 C29 122.4(8) . . ?
C31 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
C30 C31 C32 121.4(8) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C31 C32 C27 117.5(8) . . ?
C31 C32 H32 121.3 . . ?
C27 C32 H32 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C25 C1 C2 O1 -1.2(9) . . . . ?
C9 C1 C2 O1 -178.0(5) . . . . ?
C25 C1 C2 C3 178.7(5) . . . . ?
C9 C1 C2 C3 1.9(5) . . . . ?
O1 C2 C3 C4 -0.2(9) . . . . ?
C1 C2 C3 C4 179.9(5) . . . . ?
O1 C2 C3 C8 178.8(5) . . . . ?
C1 C2 C3 C8 -1.1(5) . . . . ?
C8 C3 C4 C5 0.2(8) . . . . ?
C2 C3 C4 C5 179.1(6) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C4 C5 C6 C7 -0.6(9) . . . . ?
C5 C6 C7 C8 -0.2(8) . . . . ?
C6 C7 C8 C3 1.0(7) . . . . ?
C6 C7 C8 C9 -179.0(5) . . . . ?
C4 C3 C8 C7 -1.0(8) . . . . ?
C2 C3 C8 C7 179.9(5) . . . . ?
C4 C3 C8 C9 179.0(5) . . . . ?
C2 C3 C8 C9 -0.1(6) . . . . ?
C25 C1 C9 C10 -0.5(7) . . . . ?
C2 C1 C9 C10 176.5(4) . . . . ?
C25 C1 C9 C8 -179.1(4) . . . . ?
C2 C1 C9 C8 -2.0(5) . . . . ?
C7 C8 C9 C10 3.2(9) . . . . ?
C3 C8 C9 C10 -176.9(5) . . . . ?
C7 C8 C9 C1 -178.7(5) . . . . ?
C3 C8 C9 C1 1.3(5) . . . . ?
C1 C9 C10 C18 -0.9(6) . . . . ?
C8 C9 C10 C18 177.1(5) . . . . ?
C1 C9 C10 C11 -179.8(4) . . . . ?
C8 C9 C10 C11 -1.8(9) . . . . ?
C9 C10 C11 O2 0.7(8) . . . . ?
C18 C10 C11 O2 -178.3(5) . . . . ?
C9 C10 C11 C12 -179.3(5) . . . . ?
C18 C10 C11 C12 1.7(5) . . . . ?
O2 C11 C12 C13 -2.3(8) . . . . ?
C10 C11 C12 C13 177.7(5) . . . . ?
O2 C11 C12 C17 178.6(4) . . . . ?
C10 C11 C12 C17 -1.4(5) . . . . ?
C17 C12 C13 C14 0.3(7) . . . . ?
C11 C12 C13 C14 -178.7(5) . . . . ?
C12 C13 C14 C15 -0.7(7) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C17 -0.3(8) . . . . ?
C15 C16 C17 C12 0.0(7) . . . . ?
C15 C16 C17 C18 178.2(5) . . . . ?
C13 C12 C17 C16 0.0(7) . . . . ?
C11 C12 C17 C16 179.2(4) . . . . ?
C13 C12 C17 C18 -178.6(4) . . . . ?
C11 C12 C17 C18 0.6(5) . . . . ?
C9 C10 C18 C26 1.0(7) . . . . ?
C11 C10 C18 C26 -179.9(4) . . . . ?
C9 C10 C18 C17 179.5(4) . . . . ?
C11 C10 C18 C17 -1.4(5) . . . . ?
C16 C17 C18 C26 0.5(8) . . . . ?
C12 C17 C18 C26 178.9(5) . . . . ?
C16 C17 C18 C10 -177.9(5) . . . . ?
C12 C17 C18 C10 0.5(5) . . . . ?
C24 C19 C20 C21 0.7(14) . . . . ?
C19 C20 C21 C22 4.9(13) . . . . ?
C19 C20 C21 Br1 -179.6(7) . . . . ?
C20 C21 C22 C23 -5.1(11) . . . . ?
Br1 C21 C22 C23 179.6(6) . . . . ?
C21 C22 C23 C24 -0.5(11) . . . . ?
C22 C23 C24 C19 6.0(11) . . . . ?
C22 C23 C24 C25 -178.1(6) . . . . ?
C20 C19 C24 C23 -6.0(12) . . . . ?
C20 C19 C24 C25 178.1(8) . . . . ?
C9 C1 C25 C26 2.0(7) . . . . ?
C2 C1 C25 C26 -174.4(5) . . . . ?
C9 C1 C25 C24 -176.7(5) . . . . ?
C2 C1 C25 C24 6.9(8) . . . . ?
C23 C24 C25 C1 77.5(8) . . . . ?
C19 C24 C25 C1 -106.8(7) . . . . ?
C23 C24 C25 C26 -101.2(7) . . . . ?
C19 C24 C25 C26 74.5(8) . . . . ?
C10 C18 C26 C25 0.4(7) . . . . ?
C17 C18 C26 C25 -177.7(4) . . . . ?
C10 C18 C26 C27 -178.9(5) . . . . ?
C17 C18 C26 C27 3.0(7) . . . . ?
C1 C25 C26 C18 -1.9(7) . . . . ?
C24 C25 C26 C18 176.8(4) . . . . ?
C1 C25 C26 C27 177.4(5) . . . . ?
C24 C25 C26 C27 -3.9(7) . . . . ?
C18 C26 C27 C28 -94.8(7) . . . . ?
C25 C26 C27 C28 85.9(7) . . . . ?
C18 C26 C27 C32 85.2(6) . . . . ?
C25 C26 C27 C32 -94.1(6) . . . . ?
C32 C27 C28 N1 176.5(6) . . . . ?
C26 C27 C28 N1 -3.4(9) . . . . ?
C32 C27 C28 C29 -4.0(9) . . . . ?
C26 C27 C28 C29 176.1(5) . . . . ?
N1 C28 C29 C30 -177.4(7) . . . . ?
C27 C28 C29 C30 3.1(10) . . . . ?
C28 C29 C30 C31 -2.7(13) . . . . ?
C29 C30 C31 C32 3.2(15) . . . . ?
C30 C31 C32 C27 -3.9(13) . . . . ?
C28 C27 C32 C31 4.3(10) . . . . ?
C26 C27 C32 C31 -175.7(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 H1A O2 0.86 2.37 3.201(7) 162.5 4_565

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.077


####################################################################### 
# 
# 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 1912392'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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         'C38 H30 N2 O3'
_chemical_formula_sum            'C38 H30 N2 O3'
_chemical_formula_weight         562.64

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                   11.465(2)
_cell_length_b                   11.890(3)
_cell_length_c                   12.656(3)
_cell_angle_alpha                110.391(7)
_cell_angle_beta                 108.863(6)
_cell_angle_gamma                98.617(7)
_cell_volume                     1461.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4854
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.26

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             592
_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    0.081
_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            20991
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5738
_reflns_number_gt                3102
_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)+(0.0709P)²+0.6072P] 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       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5738
_refine_ls_number_parameters     400
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.034
_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 0.6163(2) 0.4400(2) 0.1462(2) 0.0420(6) Uani 1 1 d . . . . .
C2 C 0.6668(2) 0.5637(2) 0.2540(2) 0.0441(7) Uani 1 1 d . . . . .
C3 C 0.7897(3) 0.6321(3) 0.3448(2) 0.0532(7) Uani 1 1 d . . . . .
H3 H 0.8601 0.6025 0.3437 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8047(3) 0.7451(3) 0.4368(3) 0.0642(8) Uani 1 1 d . . . . .
H4 H 0.8864 0.7908 0.4991 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7024(3) 0.7924(3) 0.4393(3) 0.0699(9) Uani 1 1 d . . . . .
H5 H 0.7158 0.8689 0.5027 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5805(3) 0.7266(3) 0.3481(3) 0.0607(8) Uani 1 1 d . . . . .
H6 H 0.5112 0.7584 0.3483 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5637(2) 0.6123(3) 0.2566(2) 0.0472(7) Uani 1 1 d . . . . .
C8 C 0.4436(3) 0.5238(3) 0.1514(2) 0.0498(7) Uani 1 1 d . . . . .
C9 C 0.4816(2) 0.4153(3) 0.0835(2) 0.0428(6) Uani 1 1 d . . . . .
C10 C 0.4108(2) 0.3037(3) -0.0206(2) 0.0452(7) Uani 1 1 d . . . . .
C11 C 0.2723(3) 0.2498(3) -0.1040(3) 0.0521(7) Uani 1 1 d . . . . .
C12 C 0.1673(3) 0.2946(3) -0.1055(3) 0.0673(9) Uani 1 1 d . . . . .
H12 H 0.1770 0.3724 -0.0460 0.081 Uiso 1 1 calc R U . . .
C13 C 0.0477(3) 0.2203(4) -0.1983(4) 0.0909(12) Uani 1 1 d . . . . .
H13 H -0.0241 0.2487 -0.2009 0.109 Uiso 1 1 calc R U . . .
C14 C 0.0325(3) 0.1042(4) -0.2873(4) 0.0951(12) Uani 1 1 d . . . . .
H14 H -0.0488 0.0570 -0.3495 0.114 Uiso 1 1 calc R U . . .
C15 C 0.1351(3) 0.0576(3) -0.2855(3) 0.0773(10) Uani 1 1 d . . . . .
H15 H 0.1245 -0.0211 -0.3440 0.093 Uiso 1 1 calc R U . . .
C16 C 0.2547(3) 0.1320(3) -0.1936(3) 0.0565(8) Uani 1 1 d . . . . .
C17 C 0.3797(3) 0.1034(3) -0.1701(3) 0.0552(8) Uani 1 1 d . . . . .
C18 C 0.4768(2) 0.2177(3) -0.0603(2) 0.0461(7) Uani 1 1 d . . . . .
C19 C 0.7158(3) 0.0762(3) 0.0176(3) 0.0761(10) Uani 1 1 d . . . . .
H19 H 0.7050 0.0890 0.0903 0.091 Uiso 1 1 calc R U . . .
C20 C 0.7752(4) -0.0122(3) -0.0252(3) 0.0882(11) Uani 1 1 d . . . . .
H20 H 0.8024 -0.0584 0.0191 0.106 Uiso 1 1 calc R U . . .
C21 C 0.7951(3) -0.0336(3) -0.1295(3) 0.0736(9) Uani 1 1 d . . . . .
C22 C 0.8594(4) -0.1306(4) -0.1761(4) 0.1174(15) Uani 1 1 d . . . . .
H22A H 0.8078 -0.1839 -0.2617 0.176 Uiso 1 1 calc R U . . .
H22B H 0.8679 -0.1803 -0.1299 0.176 Uiso 1 1 calc R U . . .
H22C H 0.9433 -0.0890 -0.1661 0.176 Uiso 1 1 calc R U . . .
C23 C 0.7555(3) 0.0374(3) -0.1900(3) 0.0796(10) Uani 1 1 d . . . . .
H23 H 0.7693 0.0264 -0.2610 0.095 Uiso 1 1 calc R U . . .
C24 C 0.6952(3) 0.1257(3) -0.1489(3) 0.0711(9) Uani 1 1 d . . . . .
H24 H 0.6696 0.1728 -0.1925 0.085 Uiso 1 1 calc R U . . .
C25 C 0.6729(2) 0.1447(3) -0.0453(2) 0.0472(7) Uani 1 1 d . . . . .
C26 C 0.6083(2) 0.2393(3) -0.0008(2) 0.0437(7) Uani 1 1 d . . . . .
C27 C 0.6805(2) 0.3540(3) 0.1059(2) 0.0435(7) Uani 1 1 d . . . . .
C28 C 0.8226(2) 0.3789(2) 0.1709(2) 0.0458(7) Uani 1 1 d . . . . .
C29 C 0.9059(3) 0.4131(3) 0.1209(3) 0.0595(8) Uani 1 1 d . . . . .
H29 H 0.8727 0.4208 0.0472 0.071 Uiso 1 1 calc R U . . .
C30 C 1.0371(3) 0.4359(3) 0.1790(3) 0.0724(9) Uani 1 1 d . . . . .
H30 H 1.0924 0.4593 0.1455 0.087 Uiso 1 1 calc R U . . .
C31 C 1.0845(3) 0.4233(3) 0.2874(3) 0.0700(9) Uani 1 1 d . . . . .
H31 H 1.1730 0.4385 0.3270 0.084 Uiso 1 1 calc R U . . .
C32 C 1.0054(3) 0.3891(3) 0.3387(3) 0.0610(8) Uani 1 1 d . . . . .
H32 H 1.0401 0.3813 0.4123 0.073 Uiso 1 1 calc R U . . .
C33 C 0.8733(3) 0.3659(3) 0.2809(3) 0.0506(7) Uani 1 1 d . . . . .
C34 C 0.8045(3) 0.2940(3) 0.4212(3) 0.0607(8) Uani 1 1 d . . . . .
C35 C 0.7211(4) 0.2484(4) 0.5602(3) 0.0963(11) Uani 1 1 d D U . . .
H35A H 0.8122 0.2643 0.6070 0.116 Uiso 1 1 calc R U . . .
H35B H 0.6882 0.3003 0.6148 0.116 Uiso 1 1 calc R U . . .
C36 C 0.6549(5) 0.1180(4) 0.5192(4) 0.1202(14) Uani 1 1 d D U . . .
H36A H 0.5657 0.1001 0.4681 0.180 Uiso 1 1 calc R U . . .
H36B H 0.6614 0.1012 0.5895 0.180 Uiso 1 1 calc R U . . .
H36C H 0.6936 0.0660 0.4729 0.180 Uiso 1 1 calc R U . . .
C37 C 0.6111(7) 0.3540(8) 0.4407(7) 0.084(2) Uani 0.506(5) 1 d D . P A 1
H37A H 0.6481 0.4304 0.4365 0.101 Uiso 0.506(5) 1 calc R U P A 1
H37B H 0.5849 0.3765 0.5091 0.101 Uiso 0.506(5) 1 calc R U P A 1
C38 C 0.4971(8) 0.2697(9) 0.3222(8) 0.122(3) Uani 0.506(5) 1 d D . P A 1
H38A H 0.5262 0.2360 0.2580 0.183 Uiso 0.506(5) 1 calc R U P A 1
H38B H 0.4401 0.3171 0.3004 0.183 Uiso 0.506(5) 1 calc R U P A 1
H38C H 0.4519 0.2022 0.3326 0.183 Uiso 0.506(5) 1 calc R U P A 1
C37' C 0.5682(7) 0.2665(8) 0.3762(8) 0.084(2) Uani 0.494(5) 1 d D . P A 2
H37C H 0.5093 0.2047 0.3835 0.101 Uiso 0.494(5) 1 calc R U P A 2
H37D H 0.5575 0.2356 0.2909 0.101 Uiso 0.494(5) 1 calc R U P A 2
C38' C 0.5371(10) 0.3903(8) 0.4140(10) 0.122(3) Uani 0.494(5) 1 d D . P A 2
H38D H 0.5351 0.4142 0.4939 0.183 Uiso 0.494(5) 1 calc R U P A 2
H38E H 0.4545 0.3811 0.3551 0.183 Uiso 0.494(5) 1 calc R U P A 2
H38F H 0.6021 0.4538 0.4169 0.183 Uiso 0.494(5) 1 calc R U P A 2
N1 N 0.7866(2) 0.3342(2) 0.3292(2) 0.0638(7) Uani 1 1 d . . . . .
H1 H 0.7110 0.3409 0.2968 0.077 Uiso 1 1 calc R U . . .
N2 N 0.7057(3) 0.2848(3) 0.4582(3) 0.0802(8) Uani 1 1 d D U . . .
O1 O 0.33697(19) 0.5387(2) 0.12796(19) 0.0715(6) Uani 1 1 d . . . . .
O2 O 0.3970(2) 0.0066(2) -0.22667(19) 0.0796(7) Uani 1 1 d . . . . .
O3 O 0.9022(2) 0.2689(2) 0.4666(2) 0.0844(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 C27 1.398(3) . ?
C1 C9 1.418(3) . ?
C1 C2 1.482(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.396(3) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.476(4) . ?
C8 O1 1.217(3) . ?
C8 C9 1.494(4) . ?
C9 C10 1.386(4) . ?
C10 C18 1.412(4) . ?
C10 C11 1.479(4) . ?
C11 C12 1.384(4) . ?
C11 C16 1.397(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.483(4) . ?
C17 O2 1.209(3) . ?
C17 C18 1.499(4) . ?
C18 C26 1.386(3) . ?
C19 C25 1.363(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(4) . ?
C20 H20 0.9300 . ?
C21 C23 1.359(4) . ?
C21 C22 1.511(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.387(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.365(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.486(3) . ?
C26 C27 1.422(4) . ?
C27 C28 1.495(3) . ?
C28 C29 1.390(4) . ?
C28 C33 1.398(3) . ?
C29 C30 1.378(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.365(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.387(4) . ?
C32 H32 0.9300 . ?
C33 N1 1.394(3) . ?
C34 O3 1.215(3) . ?
C34 N2 1.362(4) . ?
C34 N1 1.374(4) . ?
C35 C36 1.442(5) . ?
C35 N2 1.467(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 N2 1.463(7) . ?
C37 C38 1.501(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C37' N2 1.513(7) . ?
C37' C38' 1.516(8) . ?
C37' H37C 0.9700 . ?
C37' H37D 0.9700 . ?
C38' H38D 0.9600 . ?
C38' H38E 0.9600 . ?
C38' H38F 0.9600 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 C1 C9 121.6(2) . . ?
C27 C1 C2 129.9(2) . . ?
C9 C1 C2 108.5(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 132.4(2) . . ?
C7 C2 C1 108.2(2) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 121.7(3) . . ?
C6 C7 C8 128.7(2) . . ?
C2 C7 C8 109.7(2) . . ?
O1 C8 C7 125.8(3) . . ?
O1 C8 C9 128.5(3) . . ?
C7 C8 C9 105.7(2) . . ?
C10 C9 C1 119.8(2) . . ?
C10 C9 C8 132.2(2) . . ?
C1 C9 C8 108.0(2) . . ?
C9 C10 C18 118.0(2) . . ?
C9 C10 C11 133.1(2) . . ?
C18 C10 C11 108.8(2) . . ?
C12 C11 C16 119.8(3) . . ?
C12 C11 C10 132.1(3) . . ?
C16 C11 C10 108.2(2) . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 117.5(3) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C15 C16 C11 122.1(3) . . ?
C15 C16 C17 128.3(3) . . ?
C11 C16 C17 109.6(2) . . ?
O2 C17 C16 126.5(3) . . ?
O2 C17 C18 128.2(3) . . ?
C16 C17 C18 105.3(3) . . ?
C26 C18 C10 123.4(2) . . ?
C26 C18 C17 128.6(2) . . ?
C10 C18 C17 108.0(2) . . ?
C25 C19 C20 120.8(3) . . ?
C25 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 122.2(3) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C23 116.8(3) . . ?
C20 C21 C22 122.0(3) . . ?
C23 C21 C22 121.2(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 121.7(3) . . ?
C21 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 121.1(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C19 C25 C24 117.3(3) . . ?
C19 C25 C26 121.4(2) . . ?
C24 C25 C26 121.3(2) . . ?
C18 C26 C27 118.4(2) . . ?
C18 C26 C25 121.2(2) . . ?
C27 C26 C25 120.3(2) . . ?
C1 C27 C26 118.8(2) . . ?
C1 C27 C28 122.2(2) . . ?
C26 C27 C28 119.0(2) . . ?
C29 C28 C33 119.1(2) . . ?
C29 C28 C27 120.1(2) . . ?
C33 C28 C27 120.8(2) . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C32 C31 C30 121.8(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 119.9(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 N1 123.3(3) . . ?
C32 C33 C28 119.4(3) . . ?
N1 C33 C28 117.2(2) . . ?
O3 C34 N2 122.5(3) . . ?
O3 C34 N1 122.1(3) . . ?
N2 C34 N1 115.5(2) . . ?
C36 C35 N2 112.9(3) . . ?
C36 C35 H35A 109.0 . . ?
N2 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
N2 C35 H35B 109.0 . . ?
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 . . ?
N2 C37 C38 107.4(7) . . ?
N2 C37 H37A 110.2 . . ?
C38 C37 H37A 110.2 . . ?
N2 C37 H37B 110.2 . . ?
C38 C37 H37B 110.2 . . ?
H37A C37 H37B 108.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C37' C38' 109.7(7) . . ?
N2 C37' H37C 109.7 . . ?
C38' C37' H37C 109.7 . . ?
N2 C37' H37D 109.7 . . ?
C38' C37' H37D 109.7 . . ?
H37C C37' H37D 108.2 . . ?
C37' C38' H38D 109.5 . . ?
C37' C38' H38E 109.5 . . ?
H38D C38' H38E 109.5 . . ?
C37' C38' H38F 109.5 . . ?
H38D C38' H38F 109.5 . . ?
H38E C38' H38F 109.5 . . ?
C34 N1 C33 129.4(2) . . ?
C34 N1 H1 115.3 . . ?
C33 N1 H1 115.3 . . ?
C34 N2 C37 123.4(4) . . ?
C34 N2 C35 118.3(3) . . ?
C37 N2 C35 113.7(4) . . ?
C34 N2 C37' 122.8(4) . . ?
C35 N2 C37' 115.6(4) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.038

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

data_4c
_database_code_depnum_ccdc_archive 'CCDC 1912395'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H19 Cl O3'
_chemical_formula_sum            'C34 H19 Cl O3'
_chemical_formula_weight         510.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.6023(3)
_cell_length_b                   14.1593(6)
_cell_length_c                   14.3949(7)
_cell_angle_alpha                112.7911(13)
_cell_angle_beta                 94.3666(14)
_cell_angle_gamma                96.6561(14)
_cell_volume                     1406.45(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9044
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.967
_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            20143
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5504
_reflns_number_gt                4270
_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)+(0.0555P)²+0.7443P] 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         5504
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.5376(2) 0.29620(13) -0.04742(14) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.4522(2) 0.20876(14) -0.14524(14) 0.0266(4) Uani 1 1 d . . . . .
C3 C 0.4988(3) 0.24312(15) -0.22673(14) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.4550(3) 0.19015(17) -0.33051(15) 0.0360(5) Uani 1 1 d . . . . .
H4 H 0.3907 0.1233 -0.3584 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5098(3) 0.23991(19) -0.39190(16) 0.0410(5) Uani 1 1 d . . . . .
H5 H 0.4827 0.2059 -0.4621 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6042(3) 0.33923(19) -0.35003(16) 0.0376(5) Uani 1 1 d . . . . .
H6 H 0.6381 0.3712 -0.3928 0.045 Uiso 1 1 calc R U . . .
C7 C 0.6503(3) 0.39318(17) -0.24519(15) 0.0298(4) Uani 1 1 d . . . . .
H7 H 0.7142 0.4601 -0.2177 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5973(2) 0.34349(14) -0.18349(14) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.6245(2) 0.37653(14) -0.07136(13) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.7149(2) 0.46444(13) 0.00751(13) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.8214(2) 0.56129(14) 0.00941(14) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.8824(2) 0.62706(14) 0.11814(14) 0.0229(4) Uani 1 1 d . . . . .
C13 C 0.9825(2) 0.72525(14) 0.16039(16) 0.0289(4) Uani 1 1 d . . . . .
H13 H 1.0229 0.7582 0.1195 0.035 Uiso 1 1 calc R U . . .
C14 C 1.0210(3) 0.77312(15) 0.26488(16) 0.0325(5) Uani 1 1 d . . . . .
H14 H 1.0883 0.8391 0.2951 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9597(3) 0.72310(15) 0.32509(16) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.9865 0.7565 0.3954 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8592(2) 0.62417(14) 0.28258(14) 0.0259(4) Uani 1 1 d . . . . .
H16 H 0.8183 0.5916 0.3236 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8215(2) 0.57553(13) 0.17790(14) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.7195(2) 0.47269(13) 0.10899(13) 0.0191(4) Uani 1 1 d . . . . .
C19 C 0.8014(3) 0.38252(16) 0.38663(15) 0.0315(5) Uani 1 1 d . . . . .
H19 H 0.6988 0.3928 0.4182 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9520(3) 0.36790(18) 0.43601(16) 0.0376(5) Uani 1 1 d . . . . .
H20 H 0.9496 0.3682 0.5006 0.045 Uiso 1 1 calc R U . . .
C21 C 1.1074(3) 0.35268(16) 0.39071(15) 0.0315(4) Uani 1 1 d . . . . .
C22 C 1.2732(3) 0.3400(2) 0.44614(19) 0.0478(6) Uani 1 1 d . . . . .
H22A H 1.3452 0.3009 0.3977 0.072 Uiso 1 1 calc R U . . .
H22B H 1.2400 0.3040 0.4881 0.072 Uiso 1 1 calc R U . . .
H22C H 1.3401 0.4071 0.4879 0.072 Uiso 1 1 calc R U . . .
C23 C 1.1067(3) 0.35145(16) 0.29416(15) 0.0311(4) Uani 1 1 d . . . . .
H23 H 1.2093 0.3410 0.2626 0.037 Uiso 1 1 calc R U . . .
C24 C 0.9564(2) 0.36541(15) 0.24358(14) 0.0269(4) Uani 1 1 d . . . . .
H24 H 0.9583 0.3637 0.1784 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8024(2) 0.38199(13) 0.28997(13) 0.0219(4) Uani 1 1 d . . . . .
C26 C 0.6408(2) 0.40103(13) 0.23959(13) 0.0218(4) Uani 1 1 d . . . . .
C27 C 0.6379(2) 0.39234(13) 0.13126(13) 0.0196(4) Uani 1 1 d . . . . .
C28 C 0.5435(2) 0.30199(13) 0.05118(14) 0.0210(4) Uani 1 1 d . . . . .
C29 C 0.4546(2) 0.21461(14) 0.07322(14) 0.0251(4) Uani 1 1 d . . . . .
C30 C 0.2701(3) 0.19241(15) 0.06334(16) 0.0314(4) Uani 1 1 d . . . . .
H30 H 0.2006 0.2324 0.0427 0.038 Uiso 1 1 calc R U . . .
C31 C 0.1881(3) 0.11132(16) 0.08380(17) 0.0384(5) Uani 1 1 d . . . . .
H31 H 0.0642 0.0971 0.0777 0.046 Uiso 1 1 calc R U . . .
C32 C 0.2923(3) 0.05241(17) 0.11311(19) 0.0465(6) Uani 1 1 d . . . . .
C33 C 0.4753(3) 0.0723(2) 0.1238(2) 0.0622(8) Uani 1 1 d . . . . .
H33 H 0.5439 0.0314 0.1437 0.075 Uiso 1 1 calc R U . . .
C34 C 0.5561(3) 0.15439(18) 0.1044(2) 0.0482(6) Uani 1 1 d . . . . .
H34 H 0.6801 0.1693 0.1124 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 0.18889(11) -0.05235(6) 0.13496(7) 0.0802(3) Uani 1 1 d . . . . .
O1 O 0.3628(2) 0.12719(10) -0.15604(11) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.85399(18) 0.58263(10) -0.06231(10) 0.0316(3) Uani 1 1 d . . . . .
O3 O 0.51136(17) 0.42381(11) 0.28343(10) 0.0310(3) 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 C28 1.387(2) . ?
C1 C9 1.419(2) . ?
C1 C2 1.504(3) . ?
C2 O1 1.218(2) . ?
C2 C3 1.484(3) . ?
C3 C4 1.380(3) . ?
C3 C8 1.402(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.486(2) . ?
C9 C10 1.378(3) . ?
C10 C18 1.417(2) . ?
C10 C11 1.499(2) . ?
C11 O2 1.217(2) . ?
C11 C12 1.481(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.398(2) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.486(2) . ?
C18 C27 1.390(2) . ?
C19 C20 1.380(3) . ?
C19 C25 1.389(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.383(3) . ?
C21 C22 1.506(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.483(2) . ?
C26 O3 1.217(2) . ?
C26 C27 1.514(2) . ?
C27 C28 1.414(2) . ?
C28 C29 1.494(2) . ?
C29 C30 1.385(3) . ?
C29 C34 1.386(3) . ?
C30 C31 1.385(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.370(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(4) . ?
C32 Cl1 1.745(2) . ?
C33 C34 1.385(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?

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
C28 C1 C9 122.70(16) . . ?
C28 C1 C2 129.15(16) . . ?
C9 C1 C2 108.10(15) . . ?
O1 C2 C3 126.95(17) . . ?
O1 C2 C1 127.73(17) . . ?
C3 C2 C1 105.31(15) . . ?
C4 C3 C8 121.87(19) . . ?
C4 C3 C2 128.33(19) . . ?
C8 C3 C2 109.80(16) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 120.76(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C3 120.04(17) . . ?
C7 C8 C9 131.89(18) . . ?
C3 C8 C9 108.08(16) . . ?
C10 C9 C1 118.06(16) . . ?
C10 C9 C8 133.27(16) . . ?
C1 C9 C8 108.67(16) . . ?
C9 C10 C18 120.07(15) . . ?
C9 C10 C11 131.95(16) . . ?
C18 C10 C11 107.98(15) . . ?
O2 C11 C12 126.28(17) . . ?
O2 C11 C10 128.16(17) . . ?
C12 C11 C10 105.56(14) . . ?
C13 C12 C17 122.01(18) . . ?
C13 C12 C11 128.28(17) . . ?
C17 C12 C11 109.71(15) . . ?
C14 C13 C12 118.23(17) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 120.28(17) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 121.51(18) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 118.43(17) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C12 119.53(16) . . ?
C16 C17 C18 132.37(16) . . ?
C12 C17 C18 108.09(15) . . ?
C27 C18 C10 121.35(16) . . ?
C27 C18 C17 130.04(16) . . ?
C10 C18 C17 108.61(14) . . ?
C20 C19 C25 120.28(18) . . ?
C20 C19 H19 119.9 . . ?
C25 C19 H19 119.9 . . ?
C19 C20 C21 121.07(18) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C23 C21 C20 118.24(18) . . ?
C23 C21 C22 120.86(18) . . ?
C20 C21 C22 120.90(18) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 121.29(18) . . ?
C21 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 120.09(17) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C19 C25 C24 119.02(17) . . ?
C19 C25 C26 119.35(16) . . ?
C24 C25 C26 121.61(16) . . ?
O3 C26 C25 121.54(16) . . ?
O3 C26 C27 119.44(16) . . ?
C25 C26 C27 119.02(15) . . ?
C18 C27 C28 119.18(16) . . ?
C18 C27 C26 121.62(16) . . ?
C28 C27 C26 119.15(15) . . ?
C1 C28 C27 118.60(16) . . ?
C1 C28 C29 121.21(16) . . ?
C27 C28 C29 120.18(16) . . ?
C30 C29 C34 118.80(17) . . ?
C30 C29 C28 120.92(16) . . ?
C34 C29 C28 120.27(17) . . ?
C29 C30 C31 120.78(19) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 118.9(2) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C31 C32 C33 121.82(19) . . ?
C31 C32 Cl1 118.98(18) . . ?
C33 C32 Cl1 119.19(18) . . ?
C32 C33 C34 118.8(2) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C33 C34 C29 120.9(2) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.495
_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_1i
_database_code_depnum_ccdc_archive 'CCDC 1912390'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C36 H25 N O4), C H2 Cl2 '
_chemical_formula_sum            'C73 H52 Cl2 N2 O8'
_chemical_formula_weight         1156.06

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                   11.4707(9)
_cell_length_b                   17.0265(14)
_cell_length_c                   17.1384(16)
_cell_angle_alpha                68.014(3)
_cell_angle_beta                 87.526(3)
_cell_angle_gamma                70.835(2)
_cell_volume                     2919.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6670
_cell_measurement_theta_min      2.41
_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    1.315
_exptl_crystal_F_000             1204
_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    0.173
_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  0.959
_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_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            41397
_diffrn_reflns_av_unetI/netI     0.1490
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.887
_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             11448
_reflns_number_gt                5325
_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)+(0.1955P)²+8.6774P] 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         11448
_refine_ls_number_parameters     790
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.2440
_refine_ls_R_factor_gt           0.1287
_refine_ls_wR_factor_ref         0.3991
_refine_ls_wR_factor_gt          0.3281
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0372(5) 0.6769(4) 0.1653(4) 0.0325(14) Uani 1 1 d . . . . .
C2 C 1.1412(5) 0.6852(4) 0.2077(4) 0.0344(15) Uani 1 1 d . . . . .
C3 C 1.1622(6) 0.7582(4) 0.2139(4) 0.0366(15) Uani 1 1 d . . . . .
H3 H 1.1043 0.8158 0.1897 0.044 Uiso 1 1 calc R U . . .
C4 C 1.2713(6) 0.7435(5) 0.2571(4) 0.0456(17) Uani 1 1 d . . . . .
H4 H 1.2861 0.7922 0.2617 0.055 Uiso 1 1 calc R U . . .
C5 C 1.3588(6) 0.6590(5) 0.2937(4) 0.0477(19) Uani 1 1 d . . . . .
H5 H 1.4298 0.6511 0.3241 0.057 Uiso 1 1 calc R U . . .
C6 C 1.3413(6) 0.5857(5) 0.2851(4) 0.0408(17) Uani 1 1 d . . . . .
H6 H 1.4007 0.5286 0.3075 0.049 Uiso 1 1 calc R U . . .
C7 C 1.2308(6) 0.6009(4) 0.2416(4) 0.0350(15) Uani 1 1 d . . . . .
C8 C 1.1929(6) 0.5331(4) 0.2225(4) 0.0354(15) Uani 1 1 d . . . . .
C9 C 1.0709(5) 0.5871(4) 0.1704(4) 0.0298(14) Uani 1 1 d . . . . .
C10 C 0.9906(5) 0.5628(4) 0.1338(4) 0.0304(14) Uani 1 1 d . . . . .
C11 C 0.9970(6) 0.4785(4) 0.1248(4) 0.0361(15) Uani 1 1 d . . . . .
C12 C 1.0913(7) 0.3949(4) 0.1500(4) 0.0447(17) Uani 1 1 d . . . . .
H12 H 1.1665 0.3853 0.1766 0.054 Uiso 1 1 calc R U . . .
C13 C 1.0690(9) 0.3262(5) 0.1340(5) 0.063(2) Uani 1 1 d . . . . .
H13 H 1.1298 0.2696 0.1511 0.075 Uiso 1 1 calc R U . . .
C14 C 0.9581(9) 0.3410(5) 0.0932(5) 0.064(2) Uani 1 1 d . . . . .
H14 H 0.9453 0.2941 0.0834 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8657(8) 0.4242(5) 0.0666(4) 0.0500(19) Uani 1 1 d . . . . .
H15 H 0.7915 0.4342 0.0384 0.060 Uiso 1 1 calc R U . . .
C16 C 0.8869(6) 0.4921(4) 0.0830(4) 0.0376(16) Uani 1 1 d . . . . .
C17 C 0.8040(6) 0.5852(4) 0.0625(4) 0.0393(16) Uani 1 1 d . . . . .
C18 C 0.8746(5) 0.6284(4) 0.0954(4) 0.0327(14) Uani 1 1 d . . . . .
C19 C 0.6854(7) 0.8343(5) -0.0253(5) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.7474 0.8283 -0.0615 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5678(10) 0.8979(6) -0.0579(6) 0.074(3) Uani 1 1 d . . . . .
C21 C 0.5415(11) 0.9586(8) -0.1463(7) 0.112(4) Uani 1 1 d . . . . .
H21A H 0.6146 0.9462 -0.1753 0.168 Uiso 1 1 calc R U . . .
H21B H 0.5164 1.0197 -0.1502 0.168 Uiso 1 1 calc R U . . .
H21C H 0.4761 0.9501 -0.1718 0.168 Uiso 1 1 calc R U . . .
C22 C 0.4781(9) 0.9055(6) -0.0032(9) 0.087(4) Uani 1 1 d . . . . .
H22 H 0.3993 0.9474 -0.0237 0.104 Uiso 1 1 calc R U . . .
C23 C 0.5025(8) 0.8521(7) 0.0817(8) 0.079(3) Uani 1 1 d . . . . .
H23 H 0.4401 0.8577 0.1178 0.094 Uiso 1 1 calc R U . . .
C24 C 0.6174(7) 0.7912(5) 0.1128(6) 0.058(2) Uani 1 1 d . . . . .
H24 H 0.6335 0.7564 0.1703 0.069 Uiso 1 1 calc R U . . .
C25 C 0.7113(6) 0.7803(4) 0.0598(5) 0.0441(17) Uani 1 1 d . . . . .
C26 C 0.8374(6) 0.7149(4) 0.0940(4) 0.0368(15) Uani 1 1 d . . . . .
C27 C 0.9223(5) 0.7404(4) 0.1305(4) 0.0329(14) Uani 1 1 d . . . . .
C28 C 0.8849(5) 0.8325(4) 0.1322(4) 0.0363(15) Uani 1 1 d . . . . .
C29 C 0.8450(6) 0.8460(5) 0.2043(5) 0.0496(18) Uani 1 1 d . . . . .
H29 H 0.8418 0.7974 0.2520 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8098(7) 0.9298(5) 0.2074(5) 0.057(2) Uani 1 1 d . . . . .
H30 H 0.7829 0.9379 0.2567 0.068 Uiso 1 1 calc R U . . .
C31 C 0.8146(7) 1.0018(5) 0.1372(6) 0.057(2) Uani 1 1 d . . . . .
H31 H 0.7906 1.0587 0.1393 0.068 Uiso 1 1 calc R U . . .
C32 C 0.8541(6) 0.9909(5) 0.0646(5) 0.0501(19) Uani 1 1 d . . . . .
H32 H 0.8574 1.0400 0.0176 0.060 Uiso 1 1 calc R U . . .
C33 C 0.8899(6) 0.9052(4) 0.0610(4) 0.0396(16) Uani 1 1 d . . . . .
C34 C 0.9064(9) 0.9453(6) -0.0933(5) 0.0676(18) Uani 1 1 d . U . . .
C35 C 0.959(2) 0.9433(17) -0.2337(18) 0.102(4) Uani 0.551(15) 1 d D U P A 1
H35A H 0.9646 1.0027 -0.2499 0.123 Uiso 0.551(15) 1 calc R U P A 1
H35B H 0.8803 0.9496 -0.2590 0.123 Uiso 0.551(15) 1 calc R U P A 1
C36 C 1.064(2) 0.8861(13) -0.2646(11) 0.107(5) Uani 0.551(15) 1 d D U P A 1
H36A H 1.1397 0.8929 -0.2519 0.160 Uiso 0.551(15) 1 calc R U P A 1
H36B H 1.0492 0.9046 -0.3246 0.160 Uiso 0.551(15) 1 calc R U P A 1
H36C H 1.0695 0.8242 -0.2371 0.160 Uiso 0.551(15) 1 calc R U P A 1
C35' C 0.935(3) 0.965(2) -0.228(2) 0.105(5) Uani 0.449(15) 1 d D U P A 2
H35C H 1.0097 0.9750 -0.2522 0.126 Uiso 0.449(15) 1 calc R U P A 2
H35D H 0.8755 1.0222 -0.2315 0.126 Uiso 0.449(15) 1 calc R U P A 2
C36' C 0.883(3) 0.9215(16) -0.2719(14) 0.110(5) Uani 0.449(15) 1 d D U P A 2
H36D H 0.8104 0.9110 -0.2459 0.165 Uiso 0.449(15) 1 calc R U P A 2
H36E H 0.9433 0.8652 -0.2675 0.165 Uiso 0.449(15) 1 calc R U P A 2
H36F H 0.8602 0.9603 -0.3303 0.165 Uiso 0.449(15) 1 calc R U P A 2
C37 C 0.1785(8) 0.4375(5) 0.4441(4) 0.055(2) Uani 1 1 d . . . . .
C38 C 0.2168(7) 0.4979(5) 0.4673(5) 0.0534(16) Uani 1 1 d . U . . .
C39 C 0.3205(8) 0.4907(5) 0.5082(5) 0.0532(16) Uani 1 1 d . U . . .
H39 H 0.3860 0.4363 0.5266 0.064 Uiso 1 1 calc R U . . .
C40 C 0.3311(9) 0.5640(6) 0.5233(5) 0.0693(19) Uani 1 1 d . U . . .
H40 H 0.4011 0.5563 0.5547 0.083 Uiso 1 1 calc R U . . .
C41 C 0.2378(8) 0.6485(5) 0.4920(5) 0.0578(17) Uani 1 1 d . U . . .
H41 H 0.2481 0.6974 0.4991 0.069 Uiso 1 1 calc R U . . .
C42 C 0.1273(9) 0.6586(6) 0.4493(6) 0.0702(19) Uani 1 1 d . U . . .
H42 H 0.0622 0.7131 0.4309 0.084 Uiso 1 1 calc R U . . .
C43 C 0.1188(7) 0.5865(5) 0.4357(4) 0.0439(15) Uani 1 1 d . U . . .
C44 C 0.0188(9) 0.5781(6) 0.3936(5) 0.063(2) Uani 1 1 d . . . . .
C45 C 0.0536(6) 0.4848(4) 0.3960(4) 0.0374(16) Uani 1 1 d . . . . .
C46 C 0.0020(7) 0.4382(5) 0.3684(4) 0.053(2) Uani 1 1 d . . . . .
C47 C -0.1242(6) 0.4685(5) 0.3217(4) 0.0406(16) Uani 1 1 d . . . . .
C48 C -0.2203(8) 0.5480(7) 0.2904(6) 0.078(3) Uani 1 1 d . . . . .
H48 H -0.2150 0.5993 0.2954 0.094 Uiso 1 1 calc R U . . .
C49 C -0.3253(9) 0.5513(8) 0.2510(7) 0.085(3) Uani 1 1 d . . . . .
H49 H -0.3900 0.6058 0.2289 0.102 Uiso 1 1 calc R U . . .
C50 C -0.3376(9) 0.4757(9) 0.2433(6) 0.098(4) Uani 1 1 d . . . . .
H50 H -0.4100 0.4792 0.2176 0.117 Uiso 1 1 calc R U . . .
C51 C -0.2405(8) 0.3957(7) 0.2744(5) 0.064(2) Uani 1 1 d . . . . .
H51 H -0.2465 0.3446 0.2695 0.077 Uiso 1 1 calc R U . . .
C52 C -0.1344(7) 0.3915(6) 0.3128(5) 0.065(2) Uani 1 1 d . . . . .
C53 C -0.0253(7) 0.3137(5) 0.3493(4) 0.0491(18) Uani 1 1 d . . . . .
C54 C 0.0627(7) 0.3498(6) 0.3832(5) 0.057(2) Uani 1 1 d . . . . .
C55 C 0.2506(11) 0.1418(7) 0.5229(7) 0.097(2) Uani 1 1 d . U . . .
H55 H 0.2212 0.1587 0.5677 0.116 Uiso 1 1 calc R U . . .
C56 C 0.3074(15) 0.0494(8) 0.5356(10) 0.134(3) Uani 1 1 d . U . . .
C57 C 0.3408(15) -0.0189(8) 0.6158(10) 0.155(4) Uani 1 1 d . U . . .
H57A H 0.2829 -0.0031 0.6541 0.233 Uiso 1 1 calc R U . . .
H57B H 0.4225 -0.0266 0.6354 0.233 Uiso 1 1 calc R U . . .
H57C H 0.3400 -0.0740 0.6131 0.233 Uiso 1 1 calc R U . . .
C58 C 0.3539(14) 0.0261(9) 0.4709(10) 0.132(3) Uani 1 1 d . U . . .
H58 H 0.3968 -0.0339 0.4804 0.158 Uiso 1 1 calc R U . . .
C59 C 0.3383(12) 0.0891(7) 0.3930(9) 0.114(3) Uani 1 1 d . U . . .
H59 H 0.3634 0.0722 0.3476 0.137 Uiso 1 1 calc R U . . .
C60 C 0.2847(9) 0.1802(7) 0.3793(8) 0.088(2) Uani 1 1 d . U . . .
H60 H 0.2802 0.2233 0.3254 0.105 Uiso 1 1 calc R U . . .
C61 C 0.2401(8) 0.2065(6) 0.4413(6) 0.067(2) Uani 1 1 d . U . . .
C62 C 0.1794(6) 0.3031(5) 0.4281(4) 0.0497(19) Uani 1 1 d . . . . .
C63 C 0.2411(7) 0.3475(4) 0.4588(4) 0.0466(18) Uani 1 1 d . . . . .
C64 C 0.3643(6) 0.2950(4) 0.5067(4) 0.0411(16) Uani 1 1 d . . . . .
C65 C 0.3734(8) 0.2603(5) 0.5953(5) 0.057(2) Uani 1 1 d . . . . .
H65 H 0.3028 0.2750 0.6229 0.068 Uiso 1 1 calc R U . . .
C66 C 0.4836(10) 0.2055(6) 0.6417(6) 0.071(3) Uani 1 1 d . . . . .
H66 H 0.4888 0.1842 0.7004 0.086 Uiso 1 1 calc R U . . .
C67 C 0.5881(9) 0.1820(6) 0.5999(7) 0.075(3) Uani 1 1 d . . . . .
H67 H 0.6629 0.1429 0.6313 0.090 Uiso 1 1 calc R U . . .
C68 C 0.5833(7) 0.2155(5) 0.5122(6) 0.059(2) Uani 1 1 d . . . . .
H68 H 0.6540 0.1999 0.4850 0.071 Uiso 1 1 calc R U . . .
C69 C 0.4706(6) 0.2730(4) 0.4661(5) 0.0419(17) Uani 1 1 d . . . . .
C70 C 0.5365(9) 0.2757(7) 0.3272(7) 0.072(2) Uani 1 1 d . . . . .
C71 C 0.5638(10) 0.2957(8) 0.1833(7) 0.100(3) Uani 1 1 d D U . . .
H71A H 0.6479 0.2569 0.2062 0.120 Uiso 1 1 calc R U . . .
H71B H 0.5668 0.3466 0.1337 0.120 Uiso 1 1 calc R U . . .
C72 C 0.4949(10) 0.2457(8) 0.1617(7) 0.104(3) Uani 1 1 d D U . . .
H72A H 0.5051 0.1901 0.2086 0.156 Uiso 1 1 calc R U . . .
H72B H 0.5263 0.2333 0.1132 0.156 Uiso 1 1 calc R U . . .
H72C H 0.4085 0.2812 0.1493 0.156 Uiso 1 1 calc R U . . .
C1S C 0.3943(7) 0.6769(5) 0.0590(5) 0.0518(19) Uani 1 1 d . . . . .
H1S1 H 0.4659 0.6921 0.0352 0.062 Uiso 1 1 calc R U . . .
H1S2 H 0.3898 0.6796 0.1146 0.062 Uiso 1 1 calc R U . . .
Cl1S Cl 0.4115(2) 0.56790(14) 0.06804(14) 0.0707(7) Uani 1 1 d . . . . .
Cl2S Cl 0.2598(2) 0.75500(15) -0.00560(15) 0.0754(7) Uani 1 1 d . . . . .
N1 N 0.9350(5) 0.8885(4) -0.0110(4) 0.0451(14) Uani 1 1 d . . . . .
H1 H 0.9872 0.8357 -0.0017 0.054 Uiso 1 1 calc R U . . .
N2 N 0.4591(6) 0.3083(4) 0.3780(5) 0.0594(18) Uani 1 1 d . . . . .
H2 H 0.3961 0.3557 0.3534 0.071 Uiso 1 1 calc R U . . .
O1 O 1.2474(4) 0.4530(3) 0.2473(3) 0.0409(11) Uani 1 1 d . . . . .
O2 O 0.6990(5) 0.6196(3) 0.0272(3) 0.0535(13) Uani 1 1 d . . . . .
O3 O 0.8361(6) 1.0233(4) -0.1186(4) 0.0778(16) Uani 1 1 d . U . . .
O4 O 0.9632(7) 0.9014(4) -0.1418(4) 0.0838(17) Uani 1 1 d . U . . .
O5 O -0.0803(6) 0.6396(4) 0.3584(4) 0.0814(19) Uani 1 1 d . . . . .
O6 O -0.0020(6) 0.2384(4) 0.3537(4) 0.0777(17) Uani 1 1 d . . . . .
O7 O 0.6320(7) 0.2120(6) 0.3505(5) 0.106(2) Uani 1 1 d . . . . .
O8 O 0.4967(7) 0.3258(5) 0.2456(5) 0.094(2) Uani 1 1 d . 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 C27 1.383(8) . ?
C1 C9 1.418(8) . ?
C1 C2 1.494(8) . ?
C2 C7 1.383(9) . ?
C2 C3 1.384(9) . ?
C3 C4 1.383(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.502(9) . ?
C8 O1 1.208(7) . ?
C8 C9 1.501(8) . ?
C9 C10 1.380(8) . ?
C10 C18 1.415(8) . ?
C10 C11 1.479(9) . ?
C11 C16 1.387(9) . ?
C11 C12 1.396(9) . ?
C12 C13 1.398(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.470(9) . ?
C17 O2 1.222(8) . ?
C17 C18 1.501(9) . ?
C18 C26 1.383(9) . ?
C19 C25 1.383(10) . ?
C19 C20 1.399(11) . ?
C19 H19 0.9300 . ?
C20 C22 1.370(14) . ?
C20 C21 1.456(14) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.378(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.484(9) . ?
C26 C27 1.435(9) . ?
C27 C28 1.495(9) . ?
C28 C29 1.373(9) . ?
C28 C33 1.392(9) . ?
C29 C30 1.370(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.363(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.404(9) . ?
C32 H32 0.9300 . ?
C33 N1 1.408(9) . ?
C34 O3 1.225(10) . ?
C34 O4 1.331(11) . ?
C34 N1 1.357(10) . ?
C35 O4 1.46(3) . ?
C35 C36 1.498(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C35' O4 1.44(4) . ?
C35' C36' 1.495(10) . ?
C35' H35C 0.9700 . ?
C35' H35D 0.9700 . ?
C36' H36D 0.9600 . ?
C36' H36E 0.9600 . ?
C36' H36F 0.9600 . ?
C37 C63 1.390(10) . ?
C37 C38 1.423(11) . ?
C37 C45 1.493(10) . ?
C38 C39 1.354(11) . ?
C38 C43 1.470(10) . ?
C39 C40 1.410(11) . ?
C39 H39 0.9300 . ?
C40 C41 1.400(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.419(12) . ?
C41 H41 0.9300 . ?
C42 C43 1.366(11) . ?
C42 H42 0.9300 . ?
C43 C44 1.453(11) . ?
C44 O5 1.248(10) . ?
C44 C45 1.490(11) . ?
C45 C46 1.347(10) . ?
C46 C54 1.363(11) . ?
C46 C47 1.518(10) . ?
C47 C48 1.365(11) . ?
C47 C52 1.416(11) . ?
C48 C49 1.381(13) . ?
C48 H48 0.9300 . ?
C49 C50 1.394(15) . ?
C49 H49 0.9300 . ?
C50 C51 1.375(13) . ?
C50 H50 0.9300 . ?
C51 C52 1.377(11) . ?
C51 H51 0.9300 . ?
C52 C53 1.439(11) . ?
C53 O6 1.194(9) . ?
C53 C54 1.567(11) . ?
C54 C62 1.396(10) . ?
C55 C61 1.399(13) . ?
C55 C56 1.425(16) . ?
C55 H55 0.9300 . ?
C56 C58 1.346(19) . ?
C56 C57 1.394(18) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 C59 1.338(17) . ?
C58 H58 0.9300 . ?
C59 C60 1.397(14) . ?
C59 H59 0.9300 . ?
C60 C61 1.323(13) . ?
C60 H60 0.9300 . ?
C61 C62 1.492(12) . ?
C62 C63 1.425(10) . ?
C63 C64 1.480(10) . ?
C64 C69 1.391(9) . ?
C64 C65 1.403(10) . ?
C65 C66 1.363(11) . ?
C65 H65 0.9300 . ?
C66 C67 1.393(13) . ?
C66 H66 0.9300 . ?
C67 C68 1.389(12) . ?
C67 H67 0.9300 . ?
C68 C69 1.390(10) . ?
C68 H68 0.9300 . ?
C69 N2 1.394(9) . ?
C70 O7 1.212(11) . ?
C70 O8 1.341(12) . ?
C70 N2 1.351(11) . ?
C71 O8 1.439(11) . ?
C71 C72 1.481(8) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
C1S Cl1S 1.748(8) . ?
C1S Cl2S 1.753(8) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 C1 C9 122.5(5) . . ?
C27 C1 C2 129.0(6) . . ?
C9 C1 C2 108.4(5) . . ?
C7 C2 C3 119.5(6) . . ?
C7 C2 C1 107.9(6) . . ?
C3 C2 C1 132.5(6) . . ?
C4 C3 C2 118.3(6) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 122.2(7) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 117.4(6) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C2 C7 C6 122.4(6) . . ?
C2 C7 C8 110.7(5) . . ?
C6 C7 C8 127.0(6) . . ?
O1 C8 C9 128.9(6) . . ?
O1 C8 C7 126.9(6) . . ?
C9 C8 C7 104.1(5) . . ?
C10 C9 C1 119.5(5) . . ?
C10 C9 C8 131.7(5) . . ?
C1 C9 C8 108.7(5) . . ?
C9 C10 C18 118.2(5) . . ?
C9 C10 C11 133.8(6) . . ?
C18 C10 C11 108.1(5) . . ?
C16 C11 C12 120.2(6) . . ?
C16 C11 C10 108.8(5) . . ?
C12 C11 C10 131.0(6) . . ?
C11 C12 C13 117.9(7) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 121.0(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.2(7) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 118.0(7) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C15 C16 C11 121.7(6) . . ?
C15 C16 C17 128.6(6) . . ?
C11 C16 C17 109.6(6) . . ?
O2 C17 C16 127.0(6) . . ?
O2 C17 C18 127.4(6) . . ?
C16 C17 C18 105.5(5) . . ?
C26 C18 C10 123.1(6) . . ?
C26 C18 C17 128.9(6) . . ?
C10 C18 C17 107.9(5) . . ?
C25 C19 C20 121.4(8) . . ?
C25 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C22 C20 C19 118.1(9) . . ?
C22 C20 C21 119.9(10) . . ?
C19 C20 C21 121.8(11) . . ?
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 . . ?
C20 C22 C23 121.2(8) . . ?
C20 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 120.1(10) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 121.0(9) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C19 C25 C24 118.2(7) . . ?
C19 C25 C26 120.9(7) . . ?
C24 C25 C26 120.9(7) . . ?
C18 C26 C27 118.5(5) . . ?
C18 C26 C25 122.2(6) . . ?
C27 C26 C25 119.2(5) . . ?
C1 C27 C26 118.1(5) . . ?
C1 C27 C28 121.6(5) . . ?
C26 C27 C28 120.3(5) . . ?
C29 C28 C33 119.3(6) . . ?
C29 C28 C27 120.2(6) . . ?
C33 C28 C27 120.5(6) . . ?
C30 C29 C28 121.2(7) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 119.6(7) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 120.8(7) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 119.9(7) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 119.2(7) . . ?
C28 C33 N1 117.8(6) . . ?
C32 C33 N1 123.0(6) . . ?
O3 C34 O4 125.6(8) . . ?
O3 C34 N1 125.3(9) . . ?
O4 C34 N1 109.0(7) . . ?
O4 C35 C36 109.5(19) . . ?
O4 C35 H35A 109.8 . . ?
C36 C35 H35A 109.8 . . ?
O4 C35 H35B 109.8 . . ?
C36 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
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 . . ?
O4 C35' C36' 104(2) . . ?
O4 C35' H35C 111.0 . . ?
C36' C35' H35C 111.0 . . ?
O4 C35' H35D 111.0 . . ?
C36' C35' H35D 111.0 . . ?
H35C C35' H35D 109.0 . . ?
C35' C36' H36D 109.5 . . ?
C35' C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C35' C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?
C63 C37 C38 129.3(8) . . ?
C63 C37 C45 120.5(7) . . ?
C38 C37 C45 110.2(6) . . ?
C39 C38 C37 134.2(8) . . ?
C39 C38 C43 117.2(7) . . ?
C37 C38 C43 108.6(7) . . ?
C38 C39 C40 121.2(8) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C41 C40 C39 121.1(8) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C40 C41 C42 119.3(7) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
C43 C42 C41 118.5(8) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C42 C43 C44 130.2(8) . . ?
C42 C43 C38 122.5(8) . . ?
C44 C43 C38 107.2(6) . . ?
O5 C44 C43 125.9(8) . . ?
O5 C44 C45 124.3(8) . . ?
C43 C44 C45 109.7(7) . . ?
C46 C45 C44 137.0(7) . . ?
C46 C45 C37 118.8(6) . . ?
C44 C45 C37 104.2(7) . . ?
C45 C46 C54 121.0(7) . . ?
C45 C46 C47 129.5(7) . . ?
C54 C46 C47 109.5(7) . . ?
C48 C47 C52 119.2(7) . . ?
C48 C47 C46 134.6(8) . . ?
C52 C47 C46 106.1(6) . . ?
C47 C48 C49 119.1(10) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C48 C49 C50 122.2(10) . . ?
C48 C49 H49 118.9 . . ?
C50 C49 H49 118.9 . . ?
C51 C50 C49 118.6(9) . . ?
C51 C50 H50 120.7 . . ?
C49 C50 H50 120.7 . . ?
C50 C51 C52 119.9(9) . . ?
C50 C51 H51 120.0 . . ?
C52 C51 H51 120.0 . . ?
C51 C52 C47 120.9(8) . . ?
C51 C52 C53 127.1(9) . . ?
C47 C52 C53 112.0(7) . . ?
O6 C53 C52 130.3(8) . . ?
O6 C53 C54 125.9(7) . . ?
C52 C53 C54 103.9(7) . . ?
C46 C54 C62 122.0(8) . . ?
C46 C54 C53 108.4(7) . . ?
C62 C54 C53 129.3(7) . . ?
C61 C55 C56 118.2(12) . . ?
C61 C55 H55 120.9 . . ?
C56 C55 H55 120.9 . . ?
C58 C56 C57 115.9(14) . . ?
C58 C56 C55 120.3(13) . . ?
C57 C56 C55 122.6(15) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59 C58 C56 120.0(13) . . ?
C59 C58 H58 120.0 . . ?
C56 C58 H58 120.0 . . ?
C58 C59 C60 120.5(13) . . ?
C58 C59 H59 119.7 . . ?
C60 C59 H59 119.7 . . ?
C61 C60 C59 121.3(12) . . ?
C61 C60 H60 119.3 . . ?
C59 C60 H60 119.3 . . ?
C60 C61 C55 119.4(10) . . ?
C60 C61 C62 122.6(9) . . ?
C55 C61 C62 118.1(9) . . ?
C54 C62 C63 120.6(7) . . ?
C54 C62 C61 118.8(7) . . ?
C63 C62 C61 120.5(6) . . ?
C37 C63 C62 117.1(7) . . ?
C37 C63 C64 124.2(7) . . ?
C62 C63 C64 118.7(6) . . ?
C69 C64 C65 118.8(7) . . ?
C69 C64 C63 121.5(6) . . ?
C65 C64 C63 119.5(6) . . ?
C66 C65 C64 121.3(8) . . ?
C66 C65 H65 119.3 . . ?
C64 C65 H65 119.3 . . ?
C65 C66 C67 118.9(8) . . ?
C65 C66 H66 120.5 . . ?
C67 C66 H66 120.5 . . ?
C68 C67 C66 121.5(8) . . ?
C68 C67 H67 119.3 . . ?
C66 C67 H67 119.3 . . ?
C67 C68 C69 118.6(8) . . ?
C67 C68 H68 120.7 . . ?
C69 C68 H68 120.7 . . ?
C68 C69 C64 120.8(7) . . ?
C68 C69 N2 121.5(7) . . ?
C64 C69 N2 117.7(6) . . ?
O7 C70 O8 123.3(9) . . ?
O7 C70 N2 125.7(10) . . ?
O8 C70 N2 110.9(9) . . ?
O8 C71 C72 105.7(8) . . ?
O8 C71 H71A 110.6 . . ?
C72 C71 H71A 110.6 . . ?
O8 C71 H71B 110.6 . . ?
C72 C71 H71B 110.6 . . ?
H71A C71 H71B 108.7 . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
Cl1S C1S Cl2S 110.9(4) . . ?
Cl1S C1S H1S1 109.5 . . ?
Cl2S C1S H1S1 109.5 . . ?
Cl1S C1S H1S2 109.5 . . ?
Cl2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 108.1 . . ?
C34 N1 C33 128.1(7) . . ?
C34 N1 H1 116.0 . . ?
C33 N1 H1 116.0 . . ?
C70 N2 C69 126.8(7) . . ?
C70 N2 H2 116.6 . . ?
C69 N2 H2 116.6 . . ?
C34 O4 C35' 107.2(14) . . ?
C34 O4 C35 123.9(10) . . ?
C70 O8 C71 117.8(9) . . ?

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
C1S H1S1 O2 0.97 2.57 3.386(9) 141.4 .
N1 H1 Cl2S 0.86 2.98 3.656(6) 136.6 1_655
N2 H2 O1 0.86 2.26 3.065(8) 155.3 1_455

_refine_diff_density_max         1.281
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.101


####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1912394'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H22 O3'
_chemical_formula_sum            'C35 H22 O3'
_chemical_formula_weight         490.52

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

_space_group_crystal_system      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                   7.4625(5)
_cell_length_b                   14.4575(10)
_cell_length_c                   14.4842(9)
_cell_angle_alpha                111.2622(18)
_cell_angle_beta                 99.696(2)
_cell_angle_gamma                94.536(2)
_cell_volume                     1418.71(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5560
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             512
_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    0.072
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_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            19239
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5565
_reflns_number_gt                3480
_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)+(0.0836P)²+0.9557P] 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         5565
_refine_ls_number_parameters     345
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1869
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.047
_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 0.9609(4) 1.0436(2) 0.1996(2) 0.0315(6) Uani 1 1 d . . . . .
C2 C 1.0476(4) 1.1408(2) 0.2873(2) 0.0386(7) Uani 1 1 d . . . . .
C3 C 1.0015(4) 1.2208(2) 0.2502(2) 0.0390(7) Uani 1 1 d . . . . .
C4 C 1.0472(5) 1.3233(2) 0.3015(3) 0.0503(9) Uani 1 1 d . . . . .
H4 H 1.1139 1.3504 0.3681 0.060 Uiso 1 1 calc R U . . .
C5 C 0.9913(5) 1.3847(3) 0.2515(3) 0.0617(11) Uani 1 1 d . . . . .
H5 H 1.0195 1.4541 0.2844 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8932(5) 1.3426(2) 0.1523(3) 0.0550(10) Uani 1 1 d . . . . .
H6 H 0.8583 1.3850 0.1195 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8449(4) 1.2399(2) 0.0998(3) 0.0415(8) Uani 1 1 d . . . . .
H7 H 0.7783 1.2129 0.0332 0.050 Uiso 1 1 calc R U . . .
C8 C 0.9006(4) 1.1789(2) 0.1513(2) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.8731(4) 1.0679(2) 0.1187(2) 0.0298(6) Uani 1 1 d . . . . .
C10 C 0.7821(3) 0.98977(19) 0.03098(19) 0.0255(6) Uani 1 1 d . . . . .
C11 C 0.6732(4) 0.9875(2) -0.0670(2) 0.0310(6) Uani 1 1 d . . . . .
C12 C 0.6125(4) 0.8801(2) -0.13159(19) 0.0295(6) Uani 1 1 d . . . . .
C13 C 0.5109(4) 0.8380(2) -0.2299(2) 0.0392(7) Uani 1 1 d . . . . .
H13 H 0.4701 0.8783 -0.2642 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4716(4) 0.7349(3) -0.2758(2) 0.0444(8) Uani 1 1 d . . . . .
H14 H 0.4030 0.7051 -0.3419 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5330(4) 0.6752(2) -0.2246(2) 0.0420(7) Uani 1 1 d . . . . .
H15 H 0.5058 0.6057 -0.2568 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6349(4) 0.7179(2) -0.1256(2) 0.0341(7) Uani 1 1 d . . . . .
H16 H 0.6759 0.6775 -0.0915 0.041 Uiso 1 1 calc R U . . .
C17 C 0.6742(3) 0.8209(2) -0.07874(19) 0.0269(6) Uani 1 1 d . . . . .
C18 C 0.7794(3) 0.88949(19) 0.02355(19) 0.0258(6) Uani 1 1 d . . . . .
C19 C 0.7075(4) 0.6121(2) 0.1150(2) 0.0412(7) Uani 1 1 d . . . . .
H19 H 0.8109 0.5813 0.1033 0.049 Uiso 1 1 calc R U . . .
C20 C 0.5594(4) 0.5618(2) 0.1311(3) 0.0514(9) Uani 1 1 d . . . . .
H20 H 0.5639 0.4975 0.1304 0.062 Uiso 1 1 calc R U . . .
C21 C 0.4033(4) 0.6058(2) 0.1485(2) 0.0416(7) Uani 1 1 d . . . . .
C22 C 0.2384(5) 0.5497(3) 0.1637(3) 0.0623(10) Uani 1 1 d . . . . .
H22A H 0.1649 0.5968 0.1985 0.093 Uiso 1 1 calc R U . . .
H22B H 0.2792 0.5115 0.2032 0.093 Uiso 1 1 calc R U . . .
H22C H 0.1662 0.5051 0.0989 0.093 Uiso 1 1 calc R U . . .
C23 C 0.4015(4) 0.7014(2) 0.1507(2) 0.0433(8) Uani 1 1 d . . . . .
H23 H 0.2983 0.7321 0.1630 0.052 Uiso 1 1 calc R U . . .
C24 C 0.5498(4) 0.7529(2) 0.1351(2) 0.0371(7) Uani 1 1 d . . . . .
H24 H 0.5460 0.8178 0.1373 0.045 Uiso 1 1 calc R U . . .
C25 C 0.7044(3) 0.7080(2) 0.11612(19) 0.0288(6) Uani 1 1 d . . . . .
C26 C 0.8629(4) 0.7593(2) 0.09561(19) 0.0295(6) Uani 1 1 d . . . . .
C27 C 0.8639(3) 0.86640(19) 0.10404(19) 0.0265(6) Uani 1 1 d . . . . .
C28 C 0.9585(4) 0.9463(2) 0.19481(19) 0.0308(6) Uani 1 1 d . . . . .
C29 C 1.0500(4) 0.9236(2) 0.2827(2) 0.0360(7) Uani 1 1 d . U . . .
C30 C 1.2367(4) 0.9250(3) 0.3040(2) 0.0464(8) Uani 1 1 d . U . . .
H30 H 1.3082 0.9401 0.2632 0.056 Uiso 1 1 calc R U . . .
C31 C 1.3195(5) 0.9043(3) 0.3857(2) 0.0566(9) Uani 1 1 d . U . . .
H31 H 1.4461 0.9051 0.3984 0.068 Uiso 1 1 calc R U . . .
C32 C 1.2199(6) 0.8827(3) 0.4480(3) 0.0723(11) Uani 1 1 d . U . . .
C33 C 1.3105(7) 0.8613(4) 0.5380(3) 0.0978(14) Uani 1 1 d . U . . .
H33A H 1.2531 0.7976 0.5338 0.147 Uiso 1 1 calc R U . . .
H33B H 1.2971 0.9132 0.5994 0.147 Uiso 1 1 calc R U . . .
H33C H 1.4388 0.8595 0.5380 0.147 Uiso 1 1 calc R U . . .
C34 C 1.0325(6) 0.8812(4) 0.4266(3) 0.0908(14) Uani 1 1 d . U . . .
H34 H 0.9614 0.8662 0.4677 0.109 Uiso 1 1 calc R U . . .
C35 C 0.9485(5) 0.9015(3) 0.3450(3) 0.0731(11) Uani 1 1 d . U . . .
H35 H 0.8217 0.9003 0.3321 0.088 Uiso 1 1 calc R U . . .
O1 O 1.1350(3) 1.15066(17) 0.36966(16) 0.0538(6) Uani 1 1 d . . . . .
O2 O 0.6387(3) 1.05861(15) -0.08941(15) 0.0434(5) Uani 1 1 d . . . . .
O3 O 0.9926(3) 0.71709(15) 0.07155(15) 0.0415(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 C28 1.382(4) . ?
C1 C9 1.416(4) . ?
C1 C2 1.513(4) . ?
C2 O1 1.212(3) . ?
C2 C3 1.483(4) . ?
C3 C4 1.378(4) . ?
C3 C8 1.386(4) . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(4) . ?
C9 C10 1.378(4) . ?
C10 C18 1.413(4) . ?
C10 C11 1.500(4) . ?
C11 O2 1.218(3) . ?
C11 C12 1.478(4) . ?
C12 C13 1.382(4) . ?
C12 C17 1.396(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.488(4) . ?
C18 C27 1.392(3) . ?
C19 C20 1.373(4) . ?
C19 C25 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9300 . ?
C21 C23 1.372(4) . ?
C21 C22 1.511(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.381(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.475(4) . ?
C26 O3 1.218(3) . ?
C26 C27 1.507(4) . ?
C27 C28 1.420(4) . ?
C28 C29 1.497(4) . ?
C29 C30 1.372(4) . ?
C29 C35 1.376(4) . ?
C30 C31 1.382(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.364(5) . ?
C31 H31 0.9300 . ?
C32 C34 1.377(6) . ?
C32 C33 1.510(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.381(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?

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
C28 C1 C9 123.3(3) . . ?
C28 C1 C2 128.7(2) . . ?
C9 C1 C2 108.0(2) . . ?
O1 C2 C3 127.7(3) . . ?
O1 C2 C1 127.5(3) . . ?
C3 C2 C1 104.8(2) . . ?
C4 C3 C8 121.7(3) . . ?
C4 C3 C2 128.0(3) . . ?
C8 C3 C2 110.3(2) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 122.7(3) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C6 C7 C8 116.9(3) . . ?
C6 C7 H7 121.6 . . ?
C8 C7 H7 121.6 . . ?
C3 C8 C7 120.5(3) . . ?
C3 C8 C9 108.5(2) . . ?
C7 C8 C9 131.0(3) . . ?
C10 C9 C1 117.6(2) . . ?
C10 C9 C8 133.8(2) . . ?
C1 C9 C8 108.5(2) . . ?
C9 C10 C18 120.2(2) . . ?
C9 C10 C11 132.1(2) . . ?
C18 C10 C11 107.7(2) . . ?
O2 C11 C12 126.5(2) . . ?
O2 C11 C10 127.8(3) . . ?
C12 C11 C10 105.6(2) . . ?
C13 C12 C17 121.7(3) . . ?
C13 C12 C11 128.4(2) . . ?
C17 C12 C11 109.9(2) . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C12 119.5(2) . . ?
C16 C17 C18 132.7(2) . . ?
C12 C17 C18 107.7(2) . . ?
C27 C18 C10 121.7(2) . . ?
C27 C18 C17 129.3(2) . . ?
C10 C18 C17 109.0(2) . . ?
C20 C19 C25 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C25 C19 H19 119.7 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C21 C20 118.3(3) . . ?
C23 C21 C22 120.7(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 121.3(3) . . ?
C21 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C19 C25 C24 118.6(2) . . ?
C19 C25 C26 119.6(2) . . ?
C24 C25 C26 121.7(2) . . ?
O3 C26 C25 121.6(2) . . ?
O3 C26 C27 119.2(2) . . ?
C25 C26 C27 119.2(2) . . ?
C18 C27 C28 118.6(2) . . ?
C18 C27 C26 121.7(2) . . ?
C28 C27 C26 119.7(2) . . ?
C1 C28 C27 118.5(2) . . ?
C1 C28 C29 121.8(2) . . ?
C27 C28 C29 119.7(2) . . ?
C30 C29 C35 118.1(3) . . ?
C30 C29 C28 121.3(2) . . ?
C35 C29 C28 120.6(3) . . ?
C29 C30 C31 120.7(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 121.5(3) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C34 117.8(3) . . ?
C31 C32 C33 121.6(4) . . ?
C34 C32 C33 120.6(4) . . ?
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 121.1(3) . . ?
C32 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C29 C35 C34 120.8(3) . . ?
C29 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.237
_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_4d
_database_code_depnum_ccdc_archive 'CCDC 1912396'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H19 Br O3'
_chemical_formula_sum            'C34 H19 Br O3'
_chemical_formula_weight         555.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   14.3618(6)
_cell_length_b                   16.8874(8)
_cell_length_c                   19.6152(9)
_cell_angle_alpha                77.2599(14)
_cell_angle_beta                 71.5053(14)
_cell_angle_gamma                73.2936(15)
_cell_volume                     4277.2(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1692
_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    1.473
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.745
_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            61780
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.106
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             16692
_reflns_number_gt                9649
_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)+(0.0762P)²+9.7509P] 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         16692
_refine_ls_number_parameters     1030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.86357(5) 0.57540(5) 0.37279(3) 0.0631(2) Uani 1 1 d . . . . .
Br2 Br 0.07295(6) 1.13986(4) 0.96045(3) 0.0585(2) Uani 1 1 d . . . . .
Br3 Br 0.80578(6) 0.29191(6) -0.30257(4) 0.0789(3) Uani 1 1 d . . . . .
C1 C 1.0438(3) 0.6879(3) 0.6229(2) 0.0191(10) Uani 1 1 d . . . . .
C2 C 1.1453(3) 0.6580(3) 0.5704(3) 0.0233(11) Uani 1 1 d . . . . .
C3 C 1.2205(3) 0.6719(3) 0.6014(2) 0.0239(11) Uani 1 1 d . . . . .
C4 C 1.3243(4) 0.6529(3) 0.5756(3) 0.0315(12) Uani 1 1 d . . . . .
H4 H 1.3568 0.6288 0.5333 0.038 Uiso 1 1 calc R U . . .
C5 C 1.3790(4) 0.6711(3) 0.6154(3) 0.0336(13) Uani 1 1 d . . . . .
H5 H 1.4492 0.6582 0.5998 0.040 Uiso 1 1 calc R U . . .
C6 C 1.3306(4) 0.7077(3) 0.6772(3) 0.0302(12) Uani 1 1 d . . . . .
H6 H 1.3689 0.7206 0.7017 0.036 Uiso 1 1 calc R U . . .
C7 C 1.2259(3) 0.7260(3) 0.7041(3) 0.0254(11) Uani 1 1 d . . . . .
H7 H 1.1940 0.7501 0.7464 0.031 Uiso 1 1 calc R U . . .
C8 C 1.1706(3) 0.7070(3) 0.6657(2) 0.0214(10) Uani 1 1 d . . . . .
C9 C 1.0608(3) 0.7163(3) 0.6791(2) 0.0177(10) Uani 1 1 d . . . . .
C10 C 0.9784(3) 0.7451(3) 0.7346(2) 0.0168(10) Uani 1 1 d . . . . .
C11 C 0.9686(3) 0.7779(3) 0.8021(2) 0.0200(10) Uani 1 1 d . . . . .
C12 C 0.8598(3) 0.8014(3) 0.8377(2) 0.0218(10) Uani 1 1 d . . . . .
C13 C 0.8105(4) 0.8369(3) 0.9005(2) 0.0303(12) Uani 1 1 d . . . . .
H13 H 0.8466 0.8495 0.9269 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7060(4) 0.8533(3) 0.9233(3) 0.0380(13) Uani 1 1 d . . . . .
H14 H 0.6714 0.8771 0.9655 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6528(4) 0.8347(3) 0.8839(3) 0.0328(12) Uani 1 1 d . . . . .
H15 H 0.5826 0.8463 0.8999 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7021(3) 0.7988(3) 0.8205(2) 0.0269(11) Uani 1 1 d . . . . .
H16 H 0.6656 0.7870 0.7940 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8066(3) 0.7811(3) 0.7977(2) 0.0210(10) Uani 1 1 d . . . . .
C18 C 0.8800(3) 0.7450(3) 0.7335(2) 0.0178(10) Uani 1 1 d . . . . .
C19 C 0.6217(4) 0.6415(3) 0.7109(3) 0.0327(12) Uani 1 1 d . . . . .
H19 H 0.5941 0.6793 0.6761 0.039 Uiso 1 1 calc R U . . .
C20 C 0.5749(4) 0.5785(4) 0.7511(3) 0.0423(14) Uani 1 1 d . . . . .
H20 H 0.5172 0.5736 0.7422 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6130(4) 0.5223(3) 0.8050(3) 0.0323(12) Uani 1 1 d . . . . .
C22 C 0.5632(4) 0.4527(4) 0.8488(3) 0.0533(17) Uani 1 1 d . . . . .
H22A H 0.6115 0.4088 0.8681 0.080 Uiso 1 1 calc R U . . .
H22B H 0.5387 0.4312 0.8181 0.080 Uiso 1 1 calc R U . . .
H22C H 0.5077 0.4738 0.8879 0.080 Uiso 1 1 calc R U . . .
C23 C 0.7006(4) 0.5301(3) 0.8163(3) 0.0302(12) Uani 1 1 d . . . . .
H23 H 0.7272 0.4932 0.8519 0.036 Uiso 1 1 calc R U . . .
C24 C 0.7486(3) 0.5922(3) 0.7751(2) 0.0253(11) Uani 1 1 d . . . . .
H24 H 0.8075 0.5961 0.7831 0.030 Uiso 1 1 calc R U . . .
C25 C 0.7101(3) 0.6487(3) 0.7221(2) 0.0205(10) Uani 1 1 d . . . . .
C26 C 0.7593(3) 0.7156(3) 0.6772(2) 0.0202(10) Uani 1 1 d . . . . .
C27 C 0.8646(3) 0.7142(3) 0.6793(2) 0.0166(9) Uani 1 1 d . . . . .
C28 C 0.9484(3) 0.6859(3) 0.6218(2) 0.0198(10) Uani 1 1 d . . . . .
C29 C 0.9320(3) 0.6556(3) 0.5609(2) 0.0220(10) Uani 1 1 d . . . . .
C30 C 0.9499(4) 0.7006(3) 0.4918(2) 0.0281(11) Uani 1 1 d . . . . .
H30 H 0.9754 0.7477 0.4828 0.034 Uiso 1 1 calc R U . . .
C31 C 0.9301(4) 0.6759(3) 0.4359(3) 0.0315(12) Uani 1 1 d . . . . .
H31 H 0.9414 0.7066 0.3897 0.038 Uiso 1 1 calc R U . . .
C32 C 0.8938(4) 0.6058(4) 0.4497(3) 0.0348(13) Uani 1 1 d . . . . .
C33 C 0.8777(4) 0.5584(4) 0.5175(3) 0.0384(14) Uani 1 1 d . . . . .
H33 H 0.8545 0.5101 0.5258 0.046 Uiso 1 1 calc R U . . .
C34 C 0.8968(4) 0.5844(3) 0.5726(3) 0.0310(12) Uani 1 1 d . . . . .
H34 H 0.8858 0.5533 0.6187 0.037 Uiso 1 1 calc R U . . .
C35 C -0.0622(3) 0.9916(3) 0.7123(2) 0.0231(11) Uani 1 1 d . . . . .
C36 C -0.1631(4) 1.0243(3) 0.7634(3) 0.0311(12) Uani 1 1 d . . . . .
C37 C -0.2391(4) 1.0091(3) 0.7335(3) 0.0290(12) Uani 1 1 d . . . . .
C38 C -0.3432(4) 1.0284(3) 0.7599(3) 0.0399(14) Uani 1 1 d . . . . .
H38 H -0.3750 1.0548 0.8010 0.048 Uiso 1 1 calc R U . . .
C39 C -0.3983(4) 1.0073(4) 0.7234(3) 0.0463(15) Uani 1 1 d . . . . .
H39 H -0.4685 1.0200 0.7397 0.056 Uiso 1 1 calc R U . . .
C40 C -0.3500(4) 0.9672(3) 0.6625(3) 0.0396(14) Uani 1 1 d . . . . .
H40 H -0.3885 0.9519 0.6396 0.048 Uiso 1 1 calc R U . . .
C41 C -0.2448(4) 0.9492(3) 0.6347(3) 0.0303(12) Uani 1 1 d . . . . .
H41 H -0.2129 0.9234 0.5933 0.036 Uiso 1 1 calc R U . . .
C42 C -0.1903(3) 0.9713(3) 0.6714(3) 0.0235(11) Uani 1 1 d . . . . .
C43 C -0.0794(3) 0.9613(3) 0.6573(2) 0.0201(10) Uani 1 1 d . . . . .
C44 C 0.0037(3) 0.9302(3) 0.6024(2) 0.0176(10) Uani 1 1 d . . . . .
C45 C 0.0116(3) 0.8981(3) 0.5358(2) 0.0189(10) Uani 1 1 d . . . . .
C46 C 0.1222(3) 0.8741(3) 0.4994(2) 0.0197(10) Uani 1 1 d . . . . .
C47 C 0.1696(4) 0.8393(3) 0.4359(2) 0.0288(12) Uani 1 1 d . . . . .
H47 H 0.1324 0.8283 0.4094 0.035 Uiso 1 1 calc R U . . .
C48 C 0.2736(4) 0.8215(3) 0.4131(3) 0.0295(12) Uani 1 1 d . . . . .
H48 H 0.3076 0.7981 0.3707 0.035 Uiso 1 1 calc R U . . .
C49 C 0.3276(4) 0.8384(3) 0.4534(3) 0.0277(11) Uani 1 1 d . . . . .
H49 H 0.3978 0.8258 0.4373 0.033 Uiso 1 1 calc R U . . .
C50 C 0.2806(3) 0.8734(3) 0.5168(2) 0.0235(11) Uani 1 1 d . . . . .
H50 H 0.3181 0.8838 0.5434 0.028 Uiso 1 1 calc R U . . .
C51 C 0.1756(3) 0.8927(3) 0.5396(2) 0.0170(10) Uani 1 1 d . . . . .
C52 C 0.1019(3) 0.9295(3) 0.6038(2) 0.0170(10) Uani 1 1 d . . . . .
C53 C 0.3765(3) 1.0134(3) 0.6098(3) 0.0278(11) Uani 1 1 d . . . . .
H53 H 0.4082 0.9700 0.6392 0.033 Uiso 1 1 calc R U . . .
C54 C 0.4288(4) 1.0697(3) 0.5642(3) 0.0322(12) Uani 1 1 d . . . . .
H54 H 0.4959 1.0639 0.5625 0.039 Uiso 1 1 calc R U . . .
C55 C 0.3819(4) 1.1359(3) 0.5202(3) 0.0298(12) Uani 1 1 d . . . . .
C56 C 0.4384(4) 1.1986(4) 0.4703(3) 0.0498(17) Uani 1 1 d . . . . .
H56A H 0.4739 1.2162 0.4961 0.075 Uiso 1 1 calc R U . . .
H56B H 0.3915 1.2461 0.4534 0.075 Uiso 1 1 calc R U . . .
H56C H 0.4859 1.1735 0.4295 0.075 Uiso 1 1 calc R U . . .
C57 C 0.2824(4) 1.1434(3) 0.5233(3) 0.0291(12) Uani 1 1 d . . . . .
H57 H 0.2505 1.1872 0.4943 0.035 Uiso 1 1 calc R U . . .
C58 C 0.2296(4) 1.0860(3) 0.5691(2) 0.0252(11) Uani 1 1 d . . . . .
H58 H 0.1627 1.0916 0.5705 0.030 Uiso 1 1 calc R U . . .
C59 C 0.2758(3) 1.0205(3) 0.6127(2) 0.0193(10) Uani 1 1 d . . . . .
C60 C 0.2222(3) 0.9577(3) 0.6617(2) 0.0197(10) Uani 1 1 d . . . . .
C61 C 0.1177(3) 0.9603(3) 0.6583(2) 0.0182(10) Uani 1 1 d . . . . .
C62 C 0.0325(3) 0.9927(3) 0.7139(2) 0.0220(10) Uani 1 1 d . . . . .
C63 C 0.0467(3) 1.0276(3) 0.7731(2) 0.0241(11) Uani 1 1 d . . . . .
C64 C 0.0511(4) 1.1106(3) 0.7628(3) 0.0310(12) Uani 1 1 d . . . . .
H64 H 0.0479 1.1438 0.7186 0.037 Uiso 1 1 calc R U . . .
C65 C 0.0601(4) 1.1442(3) 0.8183(3) 0.0350(13) Uani 1 1 d . . . . .
H65 H 0.0626 1.1998 0.8120 0.042 Uiso 1 1 calc R U . . .
C66 C 0.0652(4) 1.0936(3) 0.8825(3) 0.0338(13) Uani 1 1 d . . . . .
C67 C 0.0642(4) 1.0100(3) 0.8935(3) 0.0394(14) Uani 1 1 d . . . . .
H67 H 0.0710 0.9764 0.9369 0.047 Uiso 1 1 calc R U . . .
C68 C 0.0528(4) 0.9776(3) 0.8387(3) 0.0323(12) Uani 1 1 d . . . . .
H68 H 0.0491 0.9222 0.8458 0.039 Uiso 1 1 calc R U . . .
C69 C 1.0373(3) 0.3617(3) -0.0626(2) 0.0196(10) Uani 1 1 d . . . . .
C70 C 1.1312(3) 0.3316(3) -0.1203(3) 0.0238(11) Uani 1 1 d . . . . .
C71 C 1.2159(3) 0.3314(3) -0.0927(3) 0.0259(11) Uani 1 1 d . . . . .
C72 C 1.3185(4) 0.3083(3) -0.1258(3) 0.0372(13) Uani 1 1 d . . . . .
H72 H 1.3424 0.2885 -0.1704 0.045 Uiso 1 1 calc R U . . .
C73 C 1.3840(4) 0.3156(4) -0.0901(3) 0.0424(14) Uani 1 1 d . . . . .
H73 H 1.4533 0.3005 -0.1110 0.051 Uiso 1 1 calc R U . . .
C74 C 1.3481(4) 0.3452(3) -0.0236(3) 0.0387(14) Uani 1 1 d . . . . .
H74 H 1.3937 0.3493 -0.0006 0.046 Uiso 1 1 calc R U . . .
C75 C 1.2452(3) 0.3688(3) 0.0091(3) 0.0276(11) Uani 1 1 d . . . . .
H75 H 1.2217 0.3898 0.0531 0.033 Uiso 1 1 calc R U . . .
C76 C 1.1783(3) 0.3607(3) -0.0247(2) 0.0214(10) Uani 1 1 d . . . . .
C77 C 1.0668(3) 0.3783(3) -0.0050(2) 0.0180(10) Uani 1 1 d . . . . .
C78 C 0.9921(3) 0.4038(3) 0.0554(2) 0.0171(10) Uani 1 1 d . . . . .
C79 C 0.9966(4) 0.4256(3) 0.1238(2) 0.0218(10) Uani 1 1 d . . . . .
C80 C 0.8897(3) 0.4504(3) 0.1674(2) 0.0193(10) Uani 1 1 d . . . . .
C81 C 0.8536(4) 0.4785(3) 0.2344(2) 0.0249(11) Uani 1 1 d . . . . .
H81 H 0.8976 0.4821 0.2590 0.030 Uiso 1 1 calc R U . . .
C82 C 0.7505(4) 0.5009(3) 0.2634(2) 0.0300(12) Uani 1 1 d . . . . .
H82 H 0.7239 0.5195 0.3085 0.036 Uiso 1 1 calc R U . . .
C83 C 0.6862(4) 0.4958(3) 0.2253(3) 0.0277(11) Uani 1 1 d . . . . .
H83 H 0.6167 0.5126 0.2449 0.033 Uiso 1 1 calc R U . . .
C84 C 0.7228(3) 0.4663(3) 0.1588(2) 0.0241(11) Uani 1 1 d . . . . .
H84 H 0.6787 0.4621 0.1346 0.029 Uiso 1 1 calc R U . . .
C85 C 0.8260(3) 0.4434(3) 0.1292(2) 0.0187(10) Uani 1 1 d . . . . .
C86 C 0.8898(3) 0.4119(3) 0.0600(2) 0.0167(10) Uani 1 1 d . . . . .
C87 C 0.6004(4) 0.3411(3) 0.0744(3) 0.0323(12) Uani 1 1 d . . . . .
H87 H 0.5633 0.3866 0.0502 0.039 Uiso 1 1 calc R U . . .
C88 C 0.5535(4) 0.2818(3) 0.1219(3) 0.0357(13) Uani 1 1 d . . . . .
H88 H 0.4846 0.2881 0.1298 0.043 Uiso 1 1 calc R U . . .
C89 C 0.6073(4) 0.2129(3) 0.1583(3) 0.0316(12) Uani 1 1 d . . . . .
C90 C 0.5558(4) 0.1481(4) 0.2104(3) 0.0485(16) Uani 1 1 d . . . . .
H90A H 0.5040 0.1741 0.2490 0.073 Uiso 1 1 calc R U . . .
H90B H 0.6046 0.1053 0.2302 0.073 Uiso 1 1 calc R U . . .
H90C H 0.5262 0.1238 0.1850 0.073 Uiso 1 1 calc R U . . .
C91 C 0.7095(4) 0.2052(3) 0.1461(2) 0.0266(11) Uani 1 1 d . . . . .
H91 H 0.7465 0.1594 0.1700 0.032 Uiso 1 1 calc R U . . .
C92 C 0.7576(3) 0.2639(3) 0.0993(2) 0.0253(11) Uani 1 1 d . . . . .
H92 H 0.8264 0.2575 0.0921 0.030 Uiso 1 1 calc R U . . .
C93 C 0.7035(3) 0.3327(3) 0.0628(2) 0.0206(10) Uani 1 1 d . . . . .
C94 C 0.7507(3) 0.3989(3) 0.0131(2) 0.0207(10) Uani 1 1 d . . . . .
C95 C 0.8612(3) 0.3923(3) 0.0055(2) 0.0187(10) Uani 1 1 d . . . . .
C96 C 0.9368(3) 0.3672(3) -0.0577(2) 0.0217(10) Uani 1 1 d . . . . .
C97 C 0.9065(3) 0.3482(3) -0.1176(2) 0.0252(11) Uani 1 1 d . . . . .
C98 C 0.8523(4) 0.2874(4) -0.1046(3) 0.0374(13) Uani 1 1 d . . . . .
H98 H 0.8355 0.2580 -0.0582 0.045 Uiso 1 1 calc R U . . .
C99 C 0.8229(4) 0.2698(4) -0.1592(3) 0.0437(15) Uani 1 1 d . . . . .
H99 H 0.7873 0.2287 -0.1497 0.052 Uiso 1 1 calc R U . . .
C100 C 0.8468(4) 0.3131(4) -0.2265(3) 0.0435(15) Uani 1 1 d . . . . .
C101 C 0.9011(4) 0.3739(4) -0.2423(3) 0.0397(14) Uani 1 1 d . . . . .
H101 H 0.9173 0.4031 -0.2889 0.048 Uiso 1 1 calc R U . . .
C102 C 0.9306(4) 0.3902(3) -0.1869(3) 0.0292(12) Uani 1 1 d . . . . .
H102 H 0.9675 0.4304 -0.1970 0.035 Uiso 1 1 calc R U . . .
O1 O 1.1616(2) 0.6299(2) 0.51505(18) 0.0334(8) Uani 1 1 d . . . . .
O2 O 1.0364(2) 0.7834(2) 0.82491(18) 0.0310(8) Uani 1 1 d . . . . .
O3 O 0.7185(2) 0.7709(2) 0.63741(17) 0.0305(8) Uani 1 1 d . . . . .
O4 O -0.1797(3) 1.0551(3) 0.8173(2) 0.0464(10) Uani 1 1 d . . . . .
O5 O -0.0553(2) 0.8920(2) 0.51318(18) 0.0296(8) Uani 1 1 d . . . . .
O6 O 0.2597(3) 0.9038(2) 0.70358(18) 0.0318(8) Uani 1 1 d . . . . .
O7 O 1.1371(2) 0.3131(2) -0.17820(18) 0.0328(8) Uani 1 1 d . . . . .
O8 O 1.0712(2) 0.4230(2) 0.14270(17) 0.0303(8) Uani 1 1 d . . . . .
O9 O 0.7039(2) 0.4590(2) -0.01927(17) 0.0304(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
Br1 C32 1.900(5) . ?
Br2 C66 1.910(4) . ?
Br3 C100 1.902(5) . ?
C1 C28 1.387(6) . ?
C1 C9 1.407(6) . ?
C1 C2 1.514(6) . ?
C2 O1 1.208(5) . ?
C2 C3 1.489(7) . ?
C3 C4 1.378(7) . ?
C3 C8 1.403(6) . ?
C4 C5 1.398(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.481(6) . ?
C9 C10 1.381(6) . ?
C10 C18 1.420(6) . ?
C10 C11 1.498(6) . ?
C11 O2 1.226(5) . ?
C11 C12 1.470(6) . ?
C12 C13 1.381(6) . ?
C12 C17 1.401(6) . ?
C13 C14 1.386(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.482(6) . ?
C18 C27 1.381(6) . ?
C19 C20 1.381(7) . ?
C19 C25 1.397(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(7) . ?
C20 H20 0.9300 . ?
C21 C23 1.389(7) . ?
C21 C22 1.510(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.385(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.476(6) . ?
C26 O3 1.217(5) . ?
C26 C27 1.519(6) . ?
C27 C28 1.413(6) . ?
C28 C29 1.503(6) . ?
C29 C34 1.381(6) . ?
C29 C30 1.384(6) . ?
C30 C31 1.388(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.380(7) . ?
C33 C34 1.381(7) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C62 1.377(6) . ?
C35 C43 1.404(6) . ?
C35 C36 1.507(7) . ?
C36 O4 1.207(6) . ?
C36 C37 1.496(7) . ?
C37 C38 1.383(7) . ?
C37 C42 1.387(7) . ?
C38 C39 1.378(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.389(8) . ?
C39 H39 0.9300 . ?
C40 C41 1.399(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.385(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.493(6) . ?
C43 C44 1.391(6) . ?
C44 C52 1.416(6) . ?
C44 C45 1.483(6) . ?
C45 O5 1.214(5) . ?
C45 C46 1.495(6) . ?
C46 C47 1.382(6) . ?
C46 C51 1.394(6) . ?
C47 C48 1.378(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.387(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.383(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.391(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.487(6) . ?
C52 C61 1.390(6) . ?
C53 C54 1.371(7) . ?
C53 C59 1.400(6) . ?
C53 H53 0.9300 . ?
C54 C55 1.399(7) . ?
C54 H54 0.9300 . ?
C55 C57 1.381(7) . ?
C55 C56 1.507(7) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 C58 1.388(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.384(6) . ?
C58 H58 0.9300 . ?
C59 C60 1.482(6) . ?
C60 O6 1.210(5) . ?
C60 C61 1.511(6) . ?
C61 C62 1.421(6) . ?
C62 C63 1.502(6) . ?
C63 C64 1.388(7) . ?
C63 C68 1.388(7) . ?
C64 C65 1.389(6) . ?
C64 H64 0.9300 . ?
C65 C66 1.367(7) . ?
C65 H65 0.9300 . ?
C66 C67 1.383(7) . ?
C67 C68 1.379(7) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
C69 C96 1.393(6) . ?
C69 C77 1.430(6) . ?
C69 C70 1.499(6) . ?
C70 O7 1.215(5) . ?
C70 C71 1.478(7) . ?
C71 C72 1.386(7) . ?
C71 C76 1.412(6) . ?
C72 C73 1.384(8) . ?
C72 H72 0.9300 . ?
C73 C74 1.390(8) . ?
C73 H73 0.9300 . ?
C74 C75 1.388(7) . ?
C74 H74 0.9300 . ?
C75 C76 1.379(6) . ?
C75 H75 0.9300 . ?
C76 C77 1.478(6) . ?
C77 C78 1.376(6) . ?
C78 C86 1.411(6) . ?
C78 C79 1.493(6) . ?
C79 O8 1.227(5) . ?
C79 C80 1.489(6) . ?
C80 C81 1.386(6) . ?
C80 C85 1.397(6) . ?
C81 C82 1.378(7) . ?
C81 H81 0.9300 . ?
C82 C83 1.389(7) . ?
C82 H82 0.9300 . ?
C83 C84 1.389(6) . ?
C83 H83 0.9300 . ?
C84 C85 1.380(6) . ?
C84 H84 0.9300 . ?
C85 C86 1.488(6) . ?
C86 C95 1.392(6) . ?
C87 C88 1.380(7) . ?
C87 C93 1.394(6) . ?
C87 H87 0.9300 . ?
C88 C89 1.387(7) . ?
C88 H88 0.9300 . ?
C89 C91 1.382(7) . ?
C89 C90 1.509(7) . ?
C90 H90A 0.9600 . ?
C90 H90B 0.9600 . ?
C90 H90C 0.9600 . ?
C91 C92 1.375(6) . ?
C91 H91 0.9300 . ?
C92 C93 1.392(6) . ?
C92 H92 0.9300 . ?
C93 C94 1.481(6) . ?
C94 O9 1.217(5) . ?
C94 C95 1.519(6) . ?
C95 C96 1.417(6) . ?
C96 C97 1.499(6) . ?
C97 C102 1.374(7) . ?
C97 C98 1.394(7) . ?
C98 C99 1.383(7) . ?
C98 H98 0.9300 . ?
C99 C100 1.352(8) . ?
C99 H99 0.9300 . ?
C100 C101 1.387(8) . ?
C101 C102 1.387(7) . ?
C101 H101 0.9300 . ?
C102 H102 0.9300 . ?

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
C28 C1 C9 122.8(4) . . ?
C28 C1 C2 129.1(4) . . ?
C9 C1 C2 108.0(4) . . ?
O1 C2 C3 127.5(4) . . ?
O1 C2 C1 127.6(4) . . ?
C3 C2 C1 104.9(4) . . ?
C4 C3 C8 121.8(4) . . ?
C4 C3 C2 128.4(4) . . ?
C8 C3 C2 109.8(4) . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.9(5) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.8(5) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C3 120.0(4) . . ?
C7 C8 C9 132.0(4) . . ?
C3 C8 C9 108.0(4) . . ?
C10 C9 C1 118.2(4) . . ?
C10 C9 C8 132.4(4) . . ?
C1 C9 C8 109.3(4) . . ?
C9 C10 C18 119.7(4) . . ?
C9 C10 C11 132.5(4) . . ?
C18 C10 C11 107.8(4) . . ?
O2 C11 C12 125.9(4) . . ?
O2 C11 C10 128.0(4) . . ?
C12 C11 C10 106.1(4) . . ?
C13 C12 C17 121.6(4) . . ?
C13 C12 C11 129.3(4) . . ?
C17 C12 C11 109.1(4) . . ?
C12 C13 C14 118.4(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C12 119.5(4) . . ?
C16 C17 C18 131.7(4) . . ?
C12 C17 C18 108.7(4) . . ?
C27 C18 C10 121.6(4) . . ?
C27 C18 C17 130.4(4) . . ?
C10 C18 C17 108.1(4) . . ?
C20 C19 C25 120.5(5) . . ?
C20 C19 H19 119.7 . . ?
C25 C19 H19 119.7 . . ?
C19 C20 C21 121.0(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C23 C21 C20 118.3(5) . . ?
C23 C21 C22 120.2(5) . . ?
C20 C21 C22 121.4(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C21 C23 H23 119.6 . . ?
C23 C24 C25 120.9(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C19 118.5(4) . . ?
C24 C25 C26 122.3(4) . . ?
C19 C25 C26 119.2(4) . . ?
O3 C26 C25 121.6(4) . . ?
O3 C26 C27 119.2(4) . . ?
C25 C26 C27 119.2(4) . . ?
C18 C27 C28 119.1(4) . . ?
C18 C27 C26 121.6(4) . . ?
C28 C27 C26 119.2(4) . . ?
C1 C28 C27 118.6(4) . . ?
C1 C28 C29 121.9(4) . . ?
C27 C28 C29 119.5(4) . . ?
C34 C29 C30 118.7(4) . . ?
C34 C29 C28 121.4(4) . . ?
C30 C29 C28 119.9(4) . . ?
C29 C30 C31 120.6(5) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 119.1(5) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C31 C32 C33 121.7(4) . . ?
C31 C32 Br1 118.1(4) . . ?
C33 C32 Br1 120.1(4) . . ?
C32 C33 C34 118.3(5) . . ?
C32 C33 H33 120.8 . . ?
C34 C33 H33 120.8 . . ?
C29 C34 C33 121.5(5) . . ?
C29 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C62 C35 C43 123.1(4) . . ?
C62 C35 C36 128.6(4) . . ?
C43 C35 C36 108.2(4) . . ?
O4 C36 C37 127.1(4) . . ?
O4 C36 C35 128.0(5) . . ?
C37 C36 C35 104.9(4) . . ?
C38 C37 C42 122.0(5) . . ?
C38 C37 C36 128.2(5) . . ?
C42 C37 C36 109.8(4) . . ?
C39 C38 C37 117.9(5) . . ?
C39 C38 H38 121.0 . . ?
C37 C38 H38 121.0 . . ?
C38 C39 C40 120.5(5) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C39 C40 C41 121.7(5) . . ?
C39 C40 H40 119.1 . . ?
C41 C40 H40 119.1 . . ?
C42 C41 C40 117.2(5) . . ?
C42 C41 H41 121.4 . . ?
C40 C41 H41 121.4 . . ?
C41 C42 C37 120.6(4) . . ?
C41 C42 C43 131.2(4) . . ?
C37 C42 C43 108.1(4) . . ?
C44 C43 C35 118.2(4) . . ?
C44 C43 C42 132.9(4) . . ?
C35 C43 C42 108.9(4) . . ?
C43 C44 C52 119.5(4) . . ?
C43 C44 C45 131.7(4) . . ?
C52 C44 C45 108.8(4) . . ?
O5 C45 C44 129.2(4) . . ?
O5 C45 C46 125.4(4) . . ?
C44 C45 C46 105.4(4) . . ?
C47 C46 C51 122.4(4) . . ?
C47 C46 C45 128.4(4) . . ?
C51 C46 C45 109.2(4) . . ?
C48 C47 C46 118.0(4) . . ?
C48 C47 H47 121.0 . . ?
C46 C47 H47 121.0 . . ?
C47 C48 C49 120.1(4) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
C50 C49 C48 122.2(4) . . ?
C50 C49 H49 118.9 . . ?
C48 C49 H49 118.9 . . ?
C49 C50 C51 118.1(4) . . ?
C49 C50 H50 121.0 . . ?
C51 C50 H50 121.0 . . ?
C50 C51 C46 119.2(4) . . ?
C50 C51 C52 132.3(4) . . ?
C46 C51 C52 108.5(4) . . ?
C61 C52 C44 121.7(4) . . ?
C61 C52 C51 130.2(4) . . ?
C44 C52 C51 108.1(4) . . ?
C54 C53 C59 120.7(4) . . ?
C54 C53 H53 119.7 . . ?
C59 C53 H53 119.7 . . ?
C53 C54 C55 120.4(4) . . ?
C53 C54 H54 119.8 . . ?
C55 C54 H54 119.8 . . ?
C57 C55 C54 119.0(4) . . ?
C57 C55 C56 120.1(4) . . ?
C54 C55 C56 120.9(4) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 C58 120.6(4) . . ?
C55 C57 H57 119.7 . . ?
C58 C57 H57 119.7 . . ?
C59 C58 C57 120.4(4) . . ?
C59 C58 H58 119.8 . . ?
C57 C58 H58 119.8 . . ?
C58 C59 C53 118.9(4) . . ?
C58 C59 C60 122.0(4) . . ?
C53 C59 C60 119.2(4) . . ?
O6 C60 C59 122.2(4) . . ?
O6 C60 C61 119.0(4) . . ?
C59 C60 C61 118.8(4) . . ?
C52 C61 C62 118.6(4) . . ?
C52 C61 C60 122.2(4) . . ?
C62 C61 C60 119.2(4) . . ?
C35 C62 C61 118.9(4) . . ?
C35 C62 C63 121.1(4) . . ?
C61 C62 C63 120.0(4) . . ?
C64 C63 C68 119.9(4) . . ?
C64 C63 C62 119.9(4) . . ?
C68 C63 C62 120.1(4) . . ?
C63 C64 C65 120.2(5) . . ?
C63 C64 H64 119.9 . . ?
C65 C64 H64 119.9 . . ?
C66 C65 C64 118.5(5) . . ?
C66 C65 H65 120.8 . . ?
C64 C65 H65 120.8 . . ?
C65 C66 C67 122.5(4) . . ?
C65 C66 Br2 118.9(4) . . ?
C67 C66 Br2 118.5(4) . . ?
C68 C67 C66 118.6(5) . . ?
C68 C67 H67 120.7 . . ?
C66 C67 H67 120.7 . . ?
C67 C68 C63 120.2(5) . . ?
C67 C68 H68 119.9 . . ?
C63 C68 H68 119.9 . . ?
C96 C69 C77 122.0(4) . . ?
C96 C69 C70 129.6(4) . . ?
C77 C69 C70 108.1(4) . . ?
O7 C70 C71 127.0(4) . . ?
O7 C70 C69 127.7(4) . . ?
C71 C70 C69 105.3(4) . . ?
C72 C71 C76 122.0(5) . . ?
C72 C71 C70 127.9(5) . . ?
C76 C71 C70 110.1(4) . . ?
C73 C72 C71 117.5(5) . . ?
C73 C72 H72 121.3 . . ?
C71 C72 H72 121.3 . . ?
C72 C73 C74 121.2(5) . . ?
C72 C73 H73 119.4 . . ?
C74 C73 H73 119.4 . . ?
C75 C74 C73 121.0(5) . . ?
C75 C74 H74 119.5 . . ?
C73 C74 H74 119.5 . . ?
C76 C75 C74 119.0(5) . . ?
C76 C75 H75 120.5 . . ?
C74 C75 H75 120.5 . . ?
C75 C76 C71 119.3(4) . . ?
C75 C76 C77 132.8(4) . . ?
C71 C76 C77 107.8(4) . . ?
C78 C77 C69 118.0(4) . . ?
C78 C77 C76 133.3(4) . . ?
C69 C77 C76 108.6(4) . . ?
C77 C78 C86 120.3(4) . . ?
C77 C78 C79 131.7(4) . . ?
C86 C78 C79 108.0(4) . . ?
O8 C79 C80 125.5(4) . . ?
O8 C79 C78 128.6(4) . . ?
C80 C79 C78 105.8(4) . . ?
C81 C80 C85 122.6(4) . . ?
C81 C80 C79 128.2(4) . . ?
C85 C80 C79 109.1(4) . . ?
C82 C81 C80 117.9(4) . . ?
C82 C81 H81 121.0 . . ?
C80 C81 H81 121.0 . . ?
C81 C82 C83 120.1(4) . . ?
C81 C82 H82 120.0 . . ?
C83 C82 H82 120.0 . . ?
C84 C83 C82 121.7(4) . . ?
C84 C83 H83 119.1 . . ?
C82 C83 H83 119.1 . . ?
C85 C84 C83 118.8(4) . . ?
C85 C84 H84 120.6 . . ?
C83 C84 H84 120.6 . . ?
C84 C85 C80 118.8(4) . . ?
C84 C85 C86 133.0(4) . . ?
C80 C85 C86 108.2(4) . . ?
C95 C86 C78 121.7(4) . . ?
C95 C86 C85 129.5(4) . . ?
C78 C86 C85 108.8(4) . . ?
C88 C87 C93 119.9(5) . . ?
C88 C87 H87 120.1 . . ?
C93 C87 H87 120.1 . . ?
C87 C88 C89 121.2(5) . . ?
C87 C88 H88 119.4 . . ?
C89 C88 H88 119.4 . . ?
C91 C89 C88 118.3(5) . . ?
C91 C89 C90 120.6(5) . . ?
C88 C89 C90 121.2(5) . . ?
C89 C90 H90A 109.5 . . ?
C89 C90 H90B 109.5 . . ?
H90A C90 H90B 109.5 . . ?
C89 C90 H90C 109.5 . . ?
H90A C90 H90C 109.5 . . ?
H90B C90 H90C 109.5 . . ?
C92 C91 C89 121.5(4) . . ?
C92 C91 H91 119.2 . . ?
C89 C91 H91 119.2 . . ?
C91 C92 C93 120.0(4) . . ?
C91 C92 H92 120.0 . . ?
C93 C92 H92 120.0 . . ?
C92 C93 C87 119.1(4) . . ?
C92 C93 C94 122.5(4) . . ?
C87 C93 C94 118.5(4) . . ?
O9 C94 C93 122.8(4) . . ?
O9 C94 C95 119.4(4) . . ?
C93 C94 C95 117.8(4) . . ?
C86 C95 C96 118.8(4) . . ?
C86 C95 C94 120.5(4) . . ?
C96 C95 C94 120.7(4) . . ?
C69 C96 C95 119.0(4) . . ?
C69 C96 C97 121.8(4) . . ?
C95 C96 C97 119.2(4) . . ?
C102 C97 C98 117.8(4) . . ?
C102 C97 C96 121.3(4) . . ?
C98 C97 C96 120.9(4) . . ?
C99 C98 C97 121.5(5) . . ?
C99 C98 H98 119.2 . . ?
C97 C98 H98 119.2 . . ?
C100 C99 C98 119.0(5) . . ?
C100 C99 H99 120.5 . . ?
C98 C99 H99 120.5 . . ?
C99 C100 C101 121.7(5) . . ?
C99 C100 Br3 120.2(4) . . ?
C101 C100 Br3 118.1(4) . . ?
C102 C101 C100 118.4(5) . . ?
C102 C101 H101 120.8 . . ?
C100 C101 H101 120.8 . . ?
C97 C102 C101 121.6(5) . . ?
C97 C102 H102 119.2 . . ?
C101 C102 H102 119.2 . . ?

_refine_diff_density_max         1.649
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.089


####################################################################### 
# 
# 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_4l
_database_code_depnum_ccdc_archive 'CCDC 1912398'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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 H19 Br O3'
_chemical_formula_sum            'C34 H19 Br O3'
_chemical_formula_weight         555.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   12.672(2)
_cell_length_b                   14.322(3)
_cell_length_c                   15.130(3)
_cell_angle_alpha                80.530(5)
_cell_angle_beta                 89.793(5)
_cell_angle_gamma                68.279(5)
_cell_volume                     2511.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4704
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.39

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1128
_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    1.673
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_T_max  0.716
_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            26921
_diffrn_reflns_av_unetI/netI     0.1512
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             9776
_reflns_number_gt                5276
_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)+(0.0684P)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         9776
_refine_ls_number_parameters     687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.45942(5) 0.81197(5) 0.13698(4) 0.03289(19) Uani 1 1 d . . . . .
Br2 Br 0.74758(6) 0.21124(5) 0.03677(4) 0.0454(2) Uani 1 1 d . . . . .
C1 C 0.9736(4) 0.6172(4) 0.3115(3) 0.0178(12) Uani 1 1 d . . . . .
C2 C 1.0762(4) 0.5576(4) 0.2656(3) 0.0214(12) Uani 1 1 d . . . . .
C3 C 1.1706(4) 0.5169(4) 0.3365(3) 0.0184(12) Uani 1 1 d . . . . .
C4 C 1.2828(4) 0.4598(4) 0.3272(3) 0.0264(13) Uani 1 1 d . . . . .
H4 H 1.3077 0.4410 0.2725 0.032 Uiso 1 1 calc R U . . .
C5 C 1.3584(5) 0.4311(4) 0.4027(3) 0.0283(14) Uani 1 1 d . . . . .
H5 H 1.4352 0.3936 0.3983 0.034 Uiso 1 1 calc R U . . .
C6 C 1.3199(4) 0.4579(4) 0.4838(4) 0.0282(14) Uani 1 1 d . . . . .
H6 H 1.3711 0.4374 0.5336 0.034 Uiso 1 1 calc R U . . .
C7 C 1.2052(4) 0.5154(4) 0.4925(3) 0.0254(13) Uani 1 1 d . . . . .
H7 H 1.1799 0.5326 0.5476 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1297(4) 0.5464(4) 0.4175(3) 0.0202(12) Uani 1 1 d . . . . .
C9 C 1.0058(4) 0.6095(4) 0.4034(3) 0.0166(12) Uani 1 1 d . . . . .
C10 C 0.9240(4) 0.6569(4) 0.4575(3) 0.0187(12) Uani 1 1 d . . . . .
C11 C 0.9287(4) 0.6636(4) 0.5561(3) 0.0215(12) Uani 1 1 d . . . . .
C12 C 0.8118(4) 0.7295(4) 0.5743(3) 0.0208(12) Uani 1 1 d . . . . .
C13 C 0.7725(4) 0.7602(4) 0.6544(3) 0.0249(13) Uani 1 1 d . . . . .
H13 H 0.8206 0.7391 0.7061 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6593(5) 0.8233(4) 0.6550(3) 0.0348(15) Uani 1 1 d . . . . .
H14 H 0.6306 0.8453 0.7078 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5883(5) 0.8540(4) 0.5772(3) 0.0372(15) Uani 1 1 d . . . . .
H15 H 0.5128 0.8972 0.5785 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6279(5) 0.8216(4) 0.4978(3) 0.0321(14) Uani 1 1 d . . . . .
H16 H 0.5791 0.8418 0.4465 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7412(4) 0.7587(4) 0.4957(3) 0.0252(13) Uani 1 1 d . . . . .
C18 C 0.8100(4) 0.7113(4) 0.4233(3) 0.0210(12) Uani 1 1 d . . . . .
C19 C 0.5338(4) 0.8977(4) 0.1667(3) 0.0235(13) Uani 1 1 d . . . . .
C20 C 0.5010(5) 0.9928(4) 0.1152(3) 0.0316(14) Uani 1 1 d . . . . .
H20 H 0.4408 1.0146 0.0722 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5571(5) 1.0566(5) 0.1270(4) 0.0459(17) Uani 1 1 d . . . . .
H21 H 0.5343 1.1215 0.0922 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6465(5) 1.0243(5) 0.1901(4) 0.0428(16) Uani 1 1 d . . . . .
H22 H 0.6865 1.0660 0.1961 0.051 Uiso 1 1 calc R U . . .
C23 C 0.6774(5) 0.9294(4) 0.2448(4) 0.0316(14) Uani 1 1 d . . . . .
H23 H 0.7358 0.9094 0.2893 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6217(4) 0.8636(4) 0.2339(3) 0.0217(13) Uani 1 1 d . . . . .
C25 C 0.6546(4) 0.7664(4) 0.2979(3) 0.0197(12) Uani 1 1 d . . . . .
C26 C 0.7780(4) 0.7164(4) 0.3341(3) 0.0199(12) Uani 1 1 d . . . . .
C27 C 0.8621(4) 0.6697(4) 0.2763(3) 0.0187(12) Uani 1 1 d . . . . .
C28 C 0.8291(4) 0.6779(4) 0.1796(3) 0.0203(12) Uani 1 1 d . . . . .
C29 C 0.8571(5) 0.7419(5) 0.1135(3) 0.0437(17) Uani 1 1 d . . . . .
H29 H 0.8997 0.7784 0.1286 0.052 Uiso 1 1 calc R U . . .
C30 C 0.8223(6) 0.7519(5) 0.0252(4) 0.0528(19) Uani 1 1 d . . . . .
H30 H 0.8413 0.7961 -0.0182 0.063 Uiso 1 1 calc R U . . .
C31 C 0.7599(5) 0.6983(5) -0.0014(3) 0.0369(16) Uani 1 1 d . . . . .
C32 C 0.7286(5) 0.7077(6) -0.0992(4) 0.063(2) Uani 1 1 d . . . . .
H32A H 0.7725 0.6454 -0.1195 0.094 Uiso 1 1 calc R U . . .
H32B H 0.7444 0.7632 -0.1334 0.094 Uiso 1 1 calc R U . . .
H32C H 0.6491 0.7205 -0.1071 0.094 Uiso 1 1 calc R U . . .
C33 C 0.7327(5) 0.6372(5) 0.0649(4) 0.0420(17) Uani 1 1 d . . . . .
H33 H 0.6904 0.6005 0.0497 0.050 Uiso 1 1 calc R U . . .
C34 C 0.7650(5) 0.6268(4) 0.1544(3) 0.0329(14) Uani 1 1 d . . . . .
H34 H 0.7429 0.5848 0.1978 0.039 Uiso 1 1 calc R U . . .
C35 C 0.7994(4) 0.2462(4) 0.4653(3) 0.0219(12) Uani 1 1 d . . . . .
C36 C 0.7074(5) 0.2947(4) 0.5244(3) 0.0267(13) Uani 1 1 d . . . . .
C37 C 0.7632(5) 0.2669(4) 0.6172(3) 0.0263(13) Uani 1 1 d . . . . .
C38 C 0.7166(5) 0.2923(5) 0.6950(4) 0.0377(15) Uani 1 1 d . . . . .
H38 H 0.6401 0.3332 0.6954 0.045 Uiso 1 1 calc R U . . .
C39 C 0.7854(6) 0.2560(5) 0.7738(4) 0.0442(17) Uani 1 1 d . . . . .
H39 H 0.7556 0.2731 0.8278 0.053 Uiso 1 1 calc R U . . .
C40 C 0.8986(6) 0.1943(5) 0.7719(4) 0.0485(19) Uani 1 1 d . . . . .
H40 H 0.9436 0.1702 0.8253 0.058 Uiso 1 1 calc R U . . .
C41 C 0.9486(5) 0.1664(4) 0.6915(3) 0.0357(15) Uani 1 1 d . . . . .
H41 H 1.0251 0.1254 0.6909 0.043 Uiso 1 1 calc R U . . .
C42 C 0.8779(5) 0.2031(4) 0.6139(3) 0.0253(13) Uani 1 1 d . . . . .
C43 C 0.9014(4) 0.1888(4) 0.5201(3) 0.0237(13) Uani 1 1 d . . . . .
C44 C 0.9950(4) 0.1310(4) 0.4793(3) 0.0218(12) Uani 1 1 d . . . . .
C45 C 1.1153(5) 0.0639(4) 0.5149(4) 0.0288(14) Uani 1 1 d . . . . .
C46 C 1.1742(4) 0.0219(4) 0.4370(4) 0.0270(13) Uani 1 1 d . . . . .
C47 C 1.2849(5) -0.0444(4) 0.4341(4) 0.0362(15) Uani 1 1 d . . . . .
H47 H 1.3331 -0.0719 0.4858 0.043 Uiso 1 1 calc R U . . .
C48 C 1.3224(5) -0.0689(5) 0.3509(4) 0.0444(17) Uani 1 1 d . . . . .
H48 H 1.3964 -0.1141 0.3471 0.053 Uiso 1 1 calc R U . . .
C49 C 1.2504(5) -0.0263(4) 0.2739(4) 0.0359(15) Uani 1 1 d . . . . .
H49 H 1.2773 -0.0419 0.2187 0.043 Uiso 1 1 calc R U . . .
C50 C 1.1388(4) 0.0392(4) 0.2782(4) 0.0298(14) Uani 1 1 d . . . . .
H50 H 1.0909 0.0670 0.2263 0.036 Uiso 1 1 calc R U . . .
C51 C 1.0999(4) 0.0626(4) 0.3588(3) 0.0213(12) Uani 1 1 d . . . . .
C52 C 0.9873(4) 0.1292(4) 0.3865(3) 0.0214(12) Uani 1 1 d . . . . .
C53 C 0.8395(4) 0.2782(4) 0.0764(3) 0.0281(14) Uani 1 1 d . . . . .
C54 C 0.8586(5) 0.3483(4) 0.0114(3) 0.0342(15) Uani 1 1 d . . . . .
H54 H 0.8316 0.3577 -0.0478 0.041 Uiso 1 1 calc R U . . .
C55 C 0.9186(5) 0.4044(5) 0.0353(4) 0.0382(16) Uani 1 1 d . . . . .
H55 H 0.9346 0.4501 -0.0086 0.046 Uiso 1 1 calc R U . . .
C56 C 0.9553(5) 0.3936(4) 0.1243(3) 0.0336(15) Uani 1 1 d . . . . .
H56 H 0.9932 0.4334 0.1406 0.040 Uiso 1 1 calc R U . . .
C57 C 0.9344(4) 0.3229(4) 0.1877(3) 0.0252(13) Uani 1 1 d . . . . .
H57 H 0.9578 0.3161 0.2474 0.030 Uiso 1 1 calc R U . . .
C58 C 0.8796(4) 0.2612(4) 0.1653(3) 0.0213(12) Uani 1 1 d . . . . .
C59 C 0.8772(4) 0.1760(4) 0.2358(3) 0.0231(13) Uani 1 1 d . . . . .
C60 C 0.8873(4) 0.1849(4) 0.3331(3) 0.0190(12) Uani 1 1 d . . . . .
C61 C 0.7928(4) 0.2480(4) 0.3733(3) 0.0220(12) Uani 1 1 d . . . . .
C62 C 0.6893(4) 0.3167(4) 0.3139(3) 0.0233(13) Uani 1 1 d . . . . .
C63 C 0.6603(4) 0.4216(4) 0.2998(3) 0.0287(14) Uani 1 1 d . . . . .
H63 H 0.7006 0.4488 0.3322 0.034 Uiso 1 1 calc R U . . .
C64 C 0.5728(4) 0.4864(5) 0.2386(4) 0.0367(16) Uani 1 1 d . . . . .
H64 H 0.5531 0.5566 0.2316 0.044 Uiso 1 1 calc R U . . .
C65 C 0.5139(5) 0.4464(5) 0.1872(3) 0.0369(16) Uani 1 1 d . . . . .
C66 C 0.4222(5) 0.5179(5) 0.1170(4) 0.062(2) Uani 1 1 d . . . . .
H66A H 0.4184 0.4831 0.0687 0.093 Uiso 1 1 calc R U . . .
H66B H 0.4400 0.5766 0.0942 0.093 Uiso 1 1 calc R U . . .
H66C H 0.3501 0.5393 0.1436 0.093 Uiso 1 1 calc R U . . .
C67 C 0.5406(5) 0.3428(5) 0.2042(4) 0.0456(17) Uani 1 1 d . . . . .
H67 H 0.4991 0.3156 0.1730 0.055 Uiso 1 1 calc R U . . .
C68 C 0.6279(4) 0.2769(4) 0.2666(4) 0.0327(14) Uani 1 1 d . . . . .
H68 H 0.6446 0.2069 0.2763 0.039 Uiso 1 1 calc R U . . .
O1 O 1.0822(3) 0.5454(3) 0.1880(2) 0.0281(9) Uani 1 1 d . . . . .
O2 O 1.0108(3) 0.6241(3) 0.6104(2) 0.0268(9) Uani 1 1 d . . . . .
O3 O 0.5882(3) 0.7256(3) 0.3221(2) 0.0327(10) Uani 1 1 d . . . . .
O4 O 0.6073(3) 0.3416(3) 0.5041(2) 0.0381(10) Uani 1 1 d . . . . .
O5 O 1.1563(3) 0.0473(3) 0.5910(2) 0.0414(11) Uani 1 1 d . . . . .
O6 O 0.8716(3) 0.0982(3) 0.2177(2) 0.0305(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 C19 1.908(5) . ?
Br2 C53 1.913(5) . ?
C1 C27 1.389(6) . ?
C1 C9 1.426(6) . ?
C1 C2 1.506(7) . ?
C2 O1 1.213(5) . ?
C2 C3 1.487(6) . ?
C3 C4 1.373(7) . ?
C3 C8 1.398(7) . ?
C4 C5 1.398(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.488(7) . ?
C9 C10 1.365(7) . ?
C10 C18 1.414(7) . ?
C10 C11 1.514(6) . ?
C11 O2 1.223(5) . ?
C11 C12 1.485(7) . ?
C12 C13 1.384(7) . ?
C12 C17 1.400(6) . ?
C13 C14 1.385(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.490(7) . ?
C18 C26 1.394(6) . ?
C19 C20 1.367(7) . ?
C19 C24 1.398(6) . ?
C20 C21 1.381(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.401(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.476(7) . ?
C25 O3 1.215(6) . ?
C25 C26 1.518(7) . ?
C26 C27 1.416(7) . ?
C27 C28 1.497(6) . ?
C28 C34 1.369(7) . ?
C28 C29 1.380(7) . ?
C29 C30 1.376(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.388(8) . ?
C30 H30 0.9300 . ?
C31 C33 1.350(8) . ?
C31 C32 1.505(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.385(7) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C61 1.390(6) . ?
C35 C43 1.424(7) . ?
C35 C36 1.496(7) . ?
C36 O4 1.208(6) . ?
C36 C37 1.498(7) . ?
C37 C38 1.358(7) . ?
C37 C42 1.407(7) . ?
C38 C39 1.386(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.381(9) . ?
C39 H39 0.9300 . ?
C40 C41 1.417(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.383(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.481(7) . ?
C43 C44 1.381(7) . ?
C44 C52 1.414(7) . ?
C44 C45 1.513(7) . ?
C45 O5 1.214(6) . ?
C45 C46 1.484(8) . ?
C46 C47 1.378(7) . ?
C46 C51 1.414(6) . ?
C47 C48 1.396(8) . ?
C47 H47 0.9300 . ?
C48 C49 1.388(8) . ?
C48 H48 0.9300 . ?
C49 C50 1.386(7) . ?
C49 H49 0.9300 . ?
C50 C51 1.361(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.497(7) . ?
C52 C60 1.393(6) . ?
C53 C54 1.374(7) . ?
C53 C58 1.389(6) . ?
C54 C55 1.380(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.392(7) . ?
C55 H55 0.9300 . ?
C56 C57 1.376(7) . ?
C56 H56 0.9300 . ?
C57 C58 1.390(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.492(7) . ?
C59 O6 1.217(6) . ?
C59 C60 1.508(7) . ?
C60 C61 1.413(7) . ?
C61 C62 1.503(7) . ?
C62 C68 1.381(7) . ?
C62 C63 1.387(7) . ?
C63 C64 1.383(7) . ?
C63 H63 0.9300 . ?
C64 C65 1.399(8) . ?
C64 H64 0.9300 . ?
C65 C67 1.373(8) . ?
C65 C66 1.516(7) . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C67 C68 1.397(7) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?

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
C27 C1 C9 122.2(5) . . ?
C27 C1 C2 128.8(4) . . ?
C9 C1 C2 109.0(4) . . ?
O1 C2 C3 126.9(5) . . ?
O1 C2 C1 128.4(4) . . ?
C3 C2 C1 104.7(4) . . ?
C4 C3 C8 122.9(4) . . ?
C4 C3 C2 127.1(5) . . ?
C8 C3 C2 109.9(4) . . ?
C3 C4 C5 117.7(5) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.9(5) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C3 118.8(5) . . ?
C7 C8 C9 132.3(5) . . ?
C3 C8 C9 109.0(4) . . ?
C10 C9 C1 118.2(4) . . ?
C10 C9 C8 134.3(4) . . ?
C1 C9 C8 107.4(4) . . ?
C9 C10 C18 120.7(4) . . ?
C9 C10 C11 131.8(4) . . ?
C18 C10 C11 107.4(4) . . ?
O2 C11 C12 126.3(4) . . ?
O2 C11 C10 127.9(5) . . ?
C12 C11 C10 105.8(4) . . ?
C13 C12 C17 122.4(5) . . ?
C13 C12 C11 128.3(4) . . ?
C17 C12 C11 109.4(4) . . ?
C12 C13 C14 118.0(5) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 118.8(5) . . ?
C16 C17 C18 132.9(5) . . ?
C12 C17 C18 108.3(4) . . ?
C26 C18 C10 121.0(5) . . ?
C26 C18 C17 130.0(5) . . ?
C10 C18 C17 109.0(4) . . ?
C20 C19 C24 121.5(5) . . ?
C20 C19 Br1 116.3(4) . . ?
C24 C19 Br1 122.1(4) . . ?
C19 C20 C21 120.2(5) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.1(6) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.7(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 117.5(5) . . ?
C19 C24 C25 124.7(5) . . ?
C23 C24 C25 117.7(4) . . ?
O3 C25 C24 123.1(5) . . ?
O3 C25 C26 119.5(4) . . ?
C24 C25 C26 117.4(4) . . ?
C18 C26 C27 119.2(4) . . ?
C18 C26 C25 121.9(4) . . ?
C27 C26 C25 118.8(4) . . ?
C1 C27 C26 118.7(4) . . ?
C1 C27 C28 121.8(4) . . ?
C26 C27 C28 119.5(4) . . ?
C34 C28 C29 117.9(5) . . ?
C34 C28 C27 121.3(4) . . ?
C29 C28 C27 120.7(4) . . ?
C30 C29 C28 120.2(5) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 122.4(5) . . ?
C29 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C33 C31 C30 116.1(5) . . ?
C33 C31 C32 123.3(6) . . ?
C30 C31 C32 120.5(6) . . ?
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 122.8(6) . . ?
C31 C33 H33 118.6 . . ?
C34 C33 H33 118.6 . . ?
C28 C34 C33 120.5(5) . . ?
C28 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C61 C35 C43 122.3(5) . . ?
C61 C35 C36 129.1(5) . . ?
C43 C35 C36 108.5(4) . . ?
O4 C36 C35 128.2(5) . . ?
O4 C36 C37 126.1(5) . . ?
C35 C36 C37 105.7(4) . . ?
C38 C37 C42 122.5(5) . . ?
C38 C37 C36 129.0(5) . . ?
C42 C37 C36 108.5(5) . . ?
C37 C38 C39 118.7(6) . . ?
C37 C38 H38 120.7 . . ?
C39 C38 H38 120.7 . . ?
C40 C39 C38 119.7(6) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
C39 C40 C41 122.5(6) . . ?
C39 C40 H40 118.8 . . ?
C41 C40 H40 118.8 . . ?
C42 C41 C40 116.6(6) . . ?
C42 C41 H41 121.7 . . ?
C40 C41 H41 121.7 . . ?
C41 C42 C37 120.0(5) . . ?
C41 C42 C43 130.8(5) . . ?
C37 C42 C43 109.2(4) . . ?
C44 C43 C35 117.8(4) . . ?
C44 C43 C42 134.1(5) . . ?
C35 C43 C42 108.0(5) . . ?
C43 C44 C52 120.1(4) . . ?
C43 C44 C45 132.3(5) . . ?
C52 C44 C45 107.6(5) . . ?
O5 C45 C46 126.6(5) . . ?
O5 C45 C44 127.7(5) . . ?
C46 C45 C44 105.6(4) . . ?
C47 C46 C51 121.3(5) . . ?
C47 C46 C45 128.7(5) . . ?
C51 C46 C45 110.0(5) . . ?
C46 C47 C48 117.9(5) . . ?
C46 C47 H47 121.1 . . ?
C48 C47 H47 121.1 . . ?
C49 C48 C47 120.7(5) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C50 C49 C48 120.7(6) . . ?
C50 C49 H49 119.6 . . ?
C48 C49 H49 119.6 . . ?
C51 C50 C49 119.6(5) . . ?
C51 C50 H50 120.2 . . ?
C49 C50 H50 120.2 . . ?
C50 C51 C46 119.8(5) . . ?
C50 C51 C52 133.1(5) . . ?
C46 C51 C52 107.1(4) . . ?
C60 C52 C44 122.1(5) . . ?
C60 C52 C51 128.3(4) . . ?
C44 C52 C51 109.6(4) . . ?
C54 C53 C58 122.2(5) . . ?
C54 C53 Br2 115.1(4) . . ?
C58 C53 Br2 122.7(4) . . ?
C53 C54 C55 118.9(5) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
C54 C55 C56 120.8(5) . . ?
C54 C55 H55 119.6 . . ?
C56 C55 H55 119.6 . . ?
C57 C56 C55 118.6(5) . . ?
C57 C56 H56 120.7 . . ?
C55 C56 H56 120.7 . . ?
C56 C57 C58 122.1(5) . . ?
C56 C57 H57 118.9 . . ?
C58 C57 H57 118.9 . . ?
C53 C58 C57 117.2(4) . . ?
C53 C58 C59 124.7(5) . . ?
C57 C58 C59 117.9(4) . . ?
O6 C59 C58 122.4(5) . . ?
O6 C59 C60 118.9(5) . . ?
C58 C59 C60 118.7(5) . . ?
C52 C60 C61 118.2(4) . . ?
C52 C60 C59 121.6(4) . . ?
C61 C60 C59 120.1(4) . . ?
C35 C61 C60 119.3(4) . . ?
C35 C61 C62 122.4(5) . . ?
C60 C61 C62 118.2(4) . . ?
C68 C62 C63 119.0(5) . . ?
C68 C62 C61 121.1(5) . . ?
C63 C62 C61 119.7(5) . . ?
C64 C63 C62 121.3(5) . . ?
C64 C63 H63 119.3 . . ?
C62 C63 H63 119.3 . . ?
C63 C64 C65 120.0(6) . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
C67 C65 C64 118.0(5) . . ?
C67 C65 C66 122.5(6) . . ?
C64 C65 C66 119.5(6) . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C65 C67 C68 122.2(6) . . ?
C65 C67 H67 118.9 . . ?
C68 C67 H67 118.9 . . ?
C62 C68 C67 119.3(6) . . ?
C62 C68 H68 120.3 . . ?
C67 C68 H68 120.3 . . ?

_refine_diff_density_max         0.984
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.096


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

data_4n
_database_code_depnum_ccdc_archive 'CCDC 1912399'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-10-01 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         'C28 H15 Br O3'
_chemical_formula_sum            'C28 H15 Br O3'
_chemical_formula_weight         479.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   16.1126(18)
_cell_length_b                   14.9541(14)
_cell_length_c                   8.7949(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.805(4)
_cell_angle_gamma                90
_cell_volume                     2048.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3973
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      22.73

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             968
_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    2.036
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.666
_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            19143
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         25.997
_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             4018
_reflns_number_gt                2256
_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)+(0.0371P)²+1.0625P] 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         4018
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.17435(3) -0.31808(3) 0.03734(6) 0.0777(2) Uani 1 1 d . . . . .
C1 C 0.3394(2) 0.1874(2) 0.2961(4) 0.0365(8) Uani 1 1 d . . . . .
C2 C 0.4115(2) 0.2227(2) 0.4242(4) 0.0377(8) Uani 1 1 d . . . . .
C3 C 0.4745(2) 0.1814(2) 0.5378(4) 0.0487(9) Uani 1 1 d . . . . .
H3 H 0.4771 0.1194 0.5450 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5341(2) 0.2344(3) 0.6419(4) 0.0573(10) Uani 1 1 d . . . . .
H4 H 0.5769 0.2070 0.7193 0.069 Uiso 1 1 calc R U . . .
C5 C 0.5313(2) 0.3259(3) 0.6328(4) 0.0586(11) Uani 1 1 d . . . . .
H5 H 0.5728 0.3597 0.7022 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4676(2) 0.3683(2) 0.5219(4) 0.0520(10) Uani 1 1 d . . . . .
H6 H 0.4647 0.4303 0.5165 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4081(2) 0.3160(2) 0.4190(4) 0.0414(8) Uani 1 1 d . . . . .
C8 C 0.3323(2) 0.3453(2) 0.2944(4) 0.0419(8) Uani 1 1 d . . . . .
C9 C 0.2901(2) 0.2612(2) 0.2219(4) 0.0384(8) Uani 1 1 d . . . . .
C10 C 0.2177(2) 0.2461(2) 0.1007(4) 0.0365(8) Uani 1 1 d . . . . .
C11 C 0.1521(2) 0.3066(2) 0.0027(4) 0.0405(8) Uani 1 1 d . . . . .
C12 C 0.1397(2) 0.3983(2) 0.0096(4) 0.0496(9) Uani 1 1 d . . . . .
H12 H 0.1772 0.4336 0.0835 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0694(2) 0.4358(2) -0.0973(4) 0.0551(10) Uani 1 1 d . . . . .
H13 H 0.0596 0.4969 -0.0931 0.066 Uiso 1 1 calc R U . . .
C14 C 0.0142(2) 0.3849(3) -0.2091(5) 0.0616(11) Uani 1 1 d . . . . .
H14 H -0.0314 0.4121 -0.2805 0.074 Uiso 1 1 calc R U . . .
C15 C 0.0261(2) 0.2927(3) -0.2163(4) 0.0538(10) Uani 1 1 d . . . . .
H15 H -0.0109 0.2577 -0.2915 0.065 Uiso 1 1 calc R U . . .
C16 C 0.0948(2) 0.2553(2) -0.1075(4) 0.0435(9) Uani 1 1 d . . . . .
C17 C 0.1171(2) 0.1588(2) -0.0832(4) 0.0442(9) Uani 1 1 d . . . . .
C18 C 0.1958(2) 0.1570(2) 0.0528(4) 0.0385(8) Uani 1 1 d . . . . .
C19 C 0.3387(2) -0.0290(2) 0.4445(4) 0.0577(10) Uani 1 1 d . . . . .
H19A H 0.3780 -0.0764 0.4869 0.087 Uiso 1 1 calc R U . . .
H19B H 0.2839 -0.0539 0.3926 0.087 Uiso 1 1 calc R U . . .
H19C H 0.3324 0.0095 0.5282 0.087 Uiso 1 1 calc R U . . .
C20 C 0.3723(2) 0.0232(2) 0.3301(4) 0.0418(8) Uani 1 1 d . . . . .
C21 C 0.31831(19) 0.1006(2) 0.2489(4) 0.0369(8) Uani 1 1 d . . . . .
C22 C 0.2443(2) 0.0843(2) 0.1237(4) 0.0380(8) Uani 1 1 d . . . . .
C23 C 0.2214(2) -0.0106(2) 0.0809(4) 0.0382(8) Uani 1 1 d . . . . .
C24 C 0.2772(2) -0.0660(2) 0.0282(4) 0.0494(9) Uani 1 1 d . . . . .
H24 H 0.3255 -0.0416 0.0047 0.059 Uiso 1 1 calc R U . . .
C25 C 0.2621(2) -0.1570(2) 0.0098(4) 0.0510(9) Uani 1 1 d . . . . .
H25 H 0.2995 -0.1933 -0.0273 0.061 Uiso 1 1 calc R U . . .
C26 C 0.1916(2) -0.1930(2) 0.0470(4) 0.0470(9) Uani 1 1 d . . . . .
C27 C 0.1330(2) -0.1385(2) 0.0911(4) 0.0495(9) Uani 1 1 d . . . . .
H27 H 0.0836 -0.1627 0.1107 0.059 Uiso 1 1 calc R U . . .
C28 C 0.1479(2) -0.0479(2) 0.1062(4) 0.0454(9) Uani 1 1 d . . . . .
H28 H 0.1075 -0.0112 0.1340 0.054 Uiso 1 1 calc R U . . .
O1 O 0.31124(15) 0.42225(16) 0.2597(3) 0.0583(7) Uani 1 1 d . . . . .
O2 O 0.07869(16) 0.09595(17) -0.1547(3) 0.0628(7) Uani 1 1 d . . . . .
O3 O 0.44070(16) 0.00743(16) 0.3036(3) 0.0600(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 C26 1.890(3) . ?
C1 C21 1.379(4) . ?
C1 C9 1.418(4) . ?
C1 C2 1.493(4) . ?
C2 C3 1.375(4) . ?
C2 C7 1.396(4) . ?
C3 C4 1.393(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(5) . ?
C8 O1 1.217(4) . ?
C8 C9 1.492(4) . ?
C9 C10 1.383(4) . ?
C10 C18 1.415(4) . ?
C10 C11 1.488(4) . ?
C11 C16 1.387(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(5) . ?
C17 O2 1.209(4) . ?
C17 C18 1.504(4) . ?
C18 C22 1.391(4) . ?
C19 C20 1.481(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O3 1.206(4) . ?
C20 C21 1.513(4) . ?
C21 C22 1.423(4) . ?
C22 C23 1.490(4) . ?
C23 C28 1.379(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.385(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(5) . ?
C27 C28 1.376(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 C1 C9 121.9(3) . . ?
C21 C1 C2 130.2(3) . . ?
C9 C1 C2 108.0(3) . . ?
C3 C2 C7 119.2(3) . . ?
C3 C2 C1 132.6(3) . . ?
C7 C2 C1 108.2(3) . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C2 121.9(3) . . ?
C6 C7 C8 128.4(3) . . ?
C2 C7 C8 109.7(3) . . ?
O1 C8 C7 126.1(3) . . ?
O1 C8 C9 128.5(3) . . ?
C7 C8 C9 105.4(3) . . ?
C10 C9 C1 119.4(3) . . ?
C10 C9 C8 132.0(3) . . ?
C1 C9 C8 108.6(3) . . ?
C9 C10 C18 118.7(3) . . ?
C9 C10 C11 133.0(3) . . ?
C18 C10 C11 108.3(3) . . ?
C16 C11 C12 119.9(3) . . ?
C16 C11 C10 108.4(3) . . ?
C12 C11 C10 131.6(3) . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 117.6(3) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C11 122.1(3) . . ?
C15 C16 C17 127.8(3) . . ?
C11 C16 C17 110.1(3) . . ?
O2 C17 C16 127.3(3) . . ?
O2 C17 C18 128.0(3) . . ?
C16 C17 C18 104.7(3) . . ?
C22 C18 C10 122.2(3) . . ?
C22 C18 C17 129.3(3) . . ?
C10 C18 C17 108.4(3) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C19 122.7(3) . . ?
O3 C20 C21 120.1(3) . . ?
C19 C20 C21 117.2(3) . . ?
C1 C21 C22 119.2(3) . . ?
C1 C21 C20 120.7(3) . . ?
C22 C21 C20 120.1(3) . . ?
C18 C22 C21 118.5(3) . . ?
C18 C22 C23 123.9(3) . . ?
C21 C22 C23 117.6(3) . . ?
C28 C23 C24 118.0(3) . . ?
C28 C23 C22 120.8(3) . . ?
C24 C23 C22 121.0(3) . . ?
C23 C24 C25 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 Br1 120.0(3) . . ?
C27 C26 Br1 119.7(3) . . ?
C28 C27 C26 119.7(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C23 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.054

