# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_y_a
_database_code_depnum_ccdc_archive 'CCDC 1854435'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;1
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Br N O'
_chemical_formula_weight         466.36

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0183(4)
_cell_length_b                   7.6583(6)
_cell_length_c                   20.8259(18)
_cell_angle_alpha                95.454(7)
_cell_angle_beta                 99.379(6)
_cell_angle_gamma                96.578(6)
_cell_volume                     1089.71(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      2.9543
_cell_measurement_theta_max      29.1887

_exptl_crystal_description       yellow
_exptl_crystal_colour            plate
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5235
_exptl_absorpt_correction_T_max  0.8624
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6813
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3831
_reflns_number_gt                2577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0613P)²+1.3157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br -0.02846(8) 0.99256(9) 0.29158(3) 0.0910(3) Uani 1 1 d . . .
O002 O 0.7755(4) 0.7453(4) 0.48881(16) 0.0605(9) Uani 1 1 d . . .
N003 N 0.3103(5) 0.4429(5) 0.82286(18) 0.0516(9) Uani 1 1 d . . .
C004 C 0.4957(6) 0.6050(5) 0.6516(2) 0.0430(10) Uani 1 1 d . . .
C005 C 0.4669(6) 0.8089(5) 0.4333(2) 0.0419(9) Uani 1 1 d . . .
C006 C 0.2804(6) 0.7941(5) 0.4486(2) 0.0435(10) Uani 1 1 d . . .
C007 C 0.4848(5) 0.7011(5) 0.5376(2) 0.0417(9) Uani 1 1 d . . .
C008 C 0.1284(6) 0.8466(6) 0.4063(2) 0.0518(11) Uani 1 1 d . . .
H008 H 0.0026 0.8375 0.4155 0.062 Uiso 1 1 calc R . .
C009 C 0.5719(6) 0.6560(5) 0.5941(2) 0.0445(10) Uani 1 1 d . . .
H009 H 0.7059 0.6572 0.5976 0.053 Uiso 1 1 calc R . .
C00A C 0.1717(6) 0.9125(6) 0.3504(2) 0.0526(11) Uani 1 1 d . . .
C00B C 0.6007(6) 0.7503(5) 0.4864(2) 0.0442(10) Uani 1 1 d . . .
C00C C 0.5060(6) 0.8730(6) 0.3766(2) 0.0500(11) Uani 1 1 d . . .
H00C H 0.6312 0.8801 0.3669 0.060 Uiso 1 1 calc R . .
C00D C 0.3564(7) 0.9267(6) 0.3342(2) 0.0535(11) Uani 1 1 d . . .
H00D H 0.3792 0.9713 0.2958 0.064 Uiso 1 1 calc R . .
C00E C 0.2984(6) 0.5678(6) 0.6551(2) 0.0503(11) Uani 1 1 d . . .
H00E H 0.2053 0.5791 0.6190 0.060 Uiso 1 1 calc R . .
C00F C 0.2745(6) 0.7198(6) 0.5128(2) 0.0479(10) Uani 1 1 d . . .
H00A H 0.1934 0.6060 0.5064 0.057 Uiso 1 1 calc R . .
H00B H 0.2253 0.8000 0.5431 0.057 Uiso 1 1 calc R . .
C00G C 0.2389(6) 0.5149(6) 0.7106(2) 0.0519(11) Uani 1 1 d . . .
H00G H 0.1065 0.4896 0.7113 0.062 Uiso 1 1 calc R . .
C00H C 0.3738(6) 0.4987(6) 0.7659(2) 0.0471(10) Uani 1 1 d . . .
C00I C 0.6275(6) 0.5863(6) 0.7072(2) 0.0563(12) Uani 1 1 d . . .
H00I H 0.7602 0.6097 0.7066 0.068 Uiso 1 1 calc R . .
C00J C 0.4120(7) 0.3251(6) 0.8593(2) 0.0566(12) Uani 1 1 d . . .
C00K C 0.1836(6) 0.5432(7) 0.8529(2) 0.0573(12) Uani 1 1 d . . .
C00L C 0.5687(6) 0.5347(6) 0.7629(2) 0.0591(12) Uani 1 1 d . . .
H00L H 0.6616 0.5238 0.7991 0.071 Uiso 1 1 calc R . .
C00M C 0.4877(8) 0.1907(7) 0.8261(3) 0.0723(15) Uani 1 1 d . . .
H00M H 0.4664 0.1767 0.7805 0.087 Uiso 1 1 calc R . .
C00N C 0.4400(9) 0.3400(7) 0.9270(2) 0.0729(15) Uani 1 1 d . . .
H00N H 0.3888 0.4284 0.9499 0.088 Uiso 1 1 calc R . .
C00O C -0.046(2) 0.736(3) 0.9170(6) 0.220(11) Uani 1 1 d . . .
H00O H -0.1169 0.8036 0.9412 0.264 Uiso 1 1 calc R . .
C00P C 0.5941(11) 0.0780(8) 0.8601(3) 0.105(2) Uani 1 1 d . . .
H00P H 0.6456 -0.0109 0.8376 0.126 Uiso 1 1 calc R . .
C00Q C 0.1959(10) 0.7208(9) 0.8523(3) 0.092(2) Uani 1 1 d . . .
H00Q H 0.2857 0.7787 0.8306 0.110 Uiso 1 1 calc R . .
C00R C 0.0448(8) 0.4574(12) 0.8841(3) 0.103(2) Uani 1 1 d . . .
H00R H 0.0288 0.3348 0.8828 0.123 Uiso 1 1 calc R . .
C00S C 0.5436(13) 0.2243(9) 0.9608(3) 0.116(3) Uani 1 1 d . . .
H00S H 0.5586 0.2330 1.0062 0.139 Uiso 1 1 calc R . .
C00T C 0.0755(19) 0.8163(17) 0.8838(4) 0.182(6) Uani 1 1 d . . .
H00T H 0.0799 0.9374 0.8815 0.218 Uiso 1 1 calc R . .
C00U C -0.0700(10) 0.559(2) 0.9173(4) 0.187(7) Uani 1 1 d . . .
H00U H -0.1617 0.5051 0.9393 0.224 Uiso 1 1 calc R . .
C00V C 0.6243(15) 0.0972(10) 0.9279(4) 0.142(4) Uani 1 1 d . . .
H00V H 0.6994 0.0235 0.9510 0.170 Uiso 1 1 calc R . .


_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
Br01 C00A 1.905(4) . ?
O002 C00B 1.225(5) . ?
N003 C00J 1.414(5) . ?
N003 C00K 1.421(6) . ?
N003 C00H 1.418(5) . ?
C004 C00I 1.390(6) . ?
C004 C00E 1.397(6) . ?
C004 C009 1.456(6) . ?
C005 C00C 1.378(6) . ?
C005 C006 1.391(5) . ?
C005 C00B 1.469(6) . ?
C006 C008 1.391(6) . ?
C006 C00F 1.507(6) . ?
C007 C009 1.331(6) . ?
C007 C00B 1.494(6) . ?
C007 C00F 1.510(5) . ?
C008 C00A 1.377(6) . ?
C00A C00D 1.387(6) . ?
C00C C00D 1.384(6) . ?
C00E C00G 1.372(6) . ?
C00G C00H 1.393(6) . ?
C00H C00L 1.377(6) . ?
C00I C00L 1.370(6) . ?
C00J C00N 1.384(7) . ?
C00J C00M 1.390(7) . ?
C00K C00Q 1.354(8) . ?
C00K C00R 1.394(8) . ?
C00M C00P 1.377(8) . ?
C00N C00S 1.382(7) . ?
C00O C00T 1.32(2) . ?
C00O C00U 1.35(2) . ?
C00P C00V 1.383(9) . ?
C00Q C00T 1.382(10) . ?
C00R C00U 1.398(13) . ?
C00S C00V 1.365(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J N003 C00K 118.9(4) . . ?
C00J N003 C00H 120.1(4) . . ?
C00K N003 C00H 118.5(4) . . ?
C00I C004 C00E 116.5(4) . . ?
C00I C004 C009 118.3(4) . . ?
C00E C004 C009 125.2(4) . . ?
C00C C005 C006 121.7(4) . . ?
C00C C005 C00B 129.1(4) . . ?
C006 C005 C00B 109.1(4) . . ?
C005 C006 C008 119.8(4) . . ?
C005 C006 C00F 111.8(3) . . ?
C008 C006 C00F 128.4(4) . . ?
C009 C007 C00B 120.5(4) . . ?
C009 C007 C00F 131.3(4) . . ?
C00B C007 C00F 108.1(3) . . ?
C00A C008 C006 117.4(4) . . ?
C007 C009 C004 131.7(4) . . ?
C008 C00A C00D 123.4(4) . . ?
C008 C00A Br01 119.5(3) . . ?
C00D C00A Br01 117.1(3) . . ?
O002 C00B C005 126.5(4) . . ?
O002 C00B C007 126.3(4) . . ?
C005 C00B C007 107.2(3) . . ?
C005 C00C C00D 119.1(4) . . ?
C00C C00D C00A 118.5(4) . . ?
C00G C00E C004 121.5(4) . . ?
C006 C00F C007 103.6(3) . . ?
C00E C00G C00H 121.0(4) . . ?
C00L C00H C00G 118.0(4) . . ?
C00L C00H N003 121.7(4) . . ?
C00G C00H N003 120.4(4) . . ?
C00L C00I C004 122.2(4) . . ?
C00N C00J C00M 118.8(4) . . ?
C00N C00J N003 122.2(4) . . ?
C00M C00J N003 119.0(4) . . ?
C00Q C00K C00R 119.3(6) . . ?
C00Q C00K N003 121.3(5) . . ?
C00R C00K N003 119.4(5) . . ?
C00I C00L C00H 120.9(4) . . ?
C00P C00M C00J 120.4(5) . . ?
C00S C00N C00J 120.4(5) . . ?
C00T C00O C00U 122.4(12) . . ?
C00M C00P C00V 120.0(6) . . ?
C00K C00Q C00T 120.3(9) . . ?
C00K C00R C00U 118.8(9) . . ?
C00V C00S C00N 120.4(6) . . ?
C00O C00T C00Q 119.9(12) . . ?
C00O C00U C00R 119.0(11) . . ?
C00S C00V C00P 120.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1854438'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H23 N O'
_chemical_formula_weight         401.48

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   14.4337(11)
_cell_length_b                   9.0667(7)
_cell_length_c                   16.5080(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.344(9)
_cell_angle_gamma                90.00
_cell_volume                     2118.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2305
_cell_measurement_theta_min      3.1296
_cell_measurement_theta_max      29.2330

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8708
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3724
_reflns_number_gt                2659
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.1925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3724
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.02159(10) 0.61871(15) 0.14442(10) 0.0470(4) Uani 1 1 d . . .
C1 C 0.65550(12) 0.87720(19) 0.11117(11) 0.0434(4) Uani 1 1 d . . .
H1 H 0.6065 0.8093 0.0983 0.052 Uiso 1 1 calc R . .
C2 C 0.75066(11) 0.81357(18) 0.12238(10) 0.0393(4) Uani 1 1 d . . .
C3 C 0.76270(12) 0.67959(19) 0.08408(11) 0.0464(5) Uani 1 1 d . . .
H3 H 0.7101 0.6333 0.0528 0.056 Uiso 1 1 calc R . .
C4 C 0.91842(12) 0.81029(18) 0.17901(11) 0.0434(4) Uani 1 1 d . . .
H4 H 0.9708 0.8545 0.2119 0.052 Uiso 1 1 calc R . .
C5 C 0.62786(11) 1.01719(19) 0.11650(10) 0.0407(4) Uani 1 1 d . . .
C6 C 0.92961(11) 0.67943(18) 0.13811(11) 0.0411(4) Uani 1 1 d . . .
O1 O 0.46651(9) 0.94438(15) 0.09415(9) 0.0634(4) Uani 1 1 d . . .
C7 C 0.49221(12) 1.1998(2) 0.11088(10) 0.0443(4) Uani 1 1 d . . .
C8 C 0.52394(12) 1.0455(2) 0.10561(11) 0.0444(4) Uani 1 1 d . . .
C9 C 1.03710(12) 0.46519(18) 0.15280(10) 0.0421(4) Uani 1 1 d . . .
C10 C 0.83089(12) 0.87537(19) 0.17152(11) 0.0433(4) Uani 1 1 d . . .
H10 H 0.8252 0.9625 0.1999 0.052 Uiso 1 1 calc R . .
C11 C 1.09195(11) 0.71219(18) 0.12097(11) 0.0412(4) Uani 1 1 d . . .
C12 C 0.85003(12) 0.6135(2) 0.09117(11) 0.0468(5) Uani 1 1 d . . .
H12 H 0.8556 0.5246 0.0644 0.056 Uiso 1 1 calc R . .
C13 C 1.18236(12) 0.7207(2) 0.16876(12) 0.0512(5) Uani 1 1 d . . .
H13 H 1.1976 0.6667 0.2174 0.061 Uiso 1 1 calc R . .
C14 C 1.07100(13) 0.7952(2) 0.04932(11) 0.0497(5) Uani 1 1 d . . .
H14 H 1.0106 0.7910 0.0168 0.060 Uiso 1 1 calc R . .
C15 C 0.98292(13) 0.3795(2) 0.19592(11) 0.0506(5) Uani 1 1 d . . .
H15 H 0.9360 0.4233 0.2191 0.061 Uiso 1 1 calc R . .
C16 C 0.55155(13) 1.3165(2) 0.09957(11) 0.0504(5) Uani 1 1 d . . .
C17 C 0.40391(13) 1.2299(2) 0.12814(12) 0.0592(5) Uani 1 1 d . . .
H17 H 0.3645 1.1523 0.1360 0.071 Uiso 1 1 calc R . .
C18 C 1.10673(12) 0.3962(2) 0.11962(11) 0.0481(5) Uani 1 1 d . . .
H18 H 1.1435 0.4513 0.0903 0.058 Uiso 1 1 calc R . .
C19 C 0.99897(15) 0.2290(2) 0.20426(13) 0.0620(6) Uani 1 1 d . . .
H19 H 0.9621 0.1723 0.2326 0.074 Uiso 1 1 calc R . .
C20 C 1.24985(13) 0.8093(2) 0.14428(14) 0.0586(6) Uani 1 1 d . . .
H20 H 1.3103 0.8143 0.1766 0.070 Uiso 1 1 calc R . .
C21 C 1.13848(14) 0.8842(2) 0.02559(12) 0.0578(5) Uani 1 1 d . . .
H21 H 1.1232 0.9403 -0.0223 0.069 Uiso 1 1 calc R . .
C22 C 1.22818(14) 0.8900(2) 0.07259(14) 0.0587(5) Uani 1 1 d . . .
H22 H 1.2741 0.9482 0.0560 0.070 Uiso 1 1 calc R . .
C23 C 1.12218(14) 0.2460(2) 0.12959(13) 0.0588(6) Uani 1 1 d . . .
H23 H 1.1698 0.2018 0.1075 0.071 Uiso 1 1 calc R . .
C24 C 0.37369(14) 1.3730(3) 0.13387(13) 0.0661(6) Uani 1 1 d . . .
H24 H 0.3148 1.3917 0.1465 0.079 Uiso 1 1 calc R . .
C25 C 0.43089(15) 1.4877(3) 0.12087(12) 0.0646(6) Uani 1 1 d . . .
H25 H 0.4101 1.5843 0.1234 0.077 Uiso 1 1 calc R . .
C26 C 1.06885(15) 0.1619(2) 0.17112(14) 0.0623(6) Uani 1 1 d . . .
H26 H 1.0793 0.0610 0.1771 0.075 Uiso 1 1 calc R . .
C27 C 0.51879(15) 1.4605(2) 0.10412(13) 0.0600(5) Uani 1 1 d . . .
H27 H 0.5571 1.5392 0.0957 0.072 Uiso 1 1 calc R . .
C28 C 0.69160(12) 1.15016(19) 0.13173(13) 0.0522(5) Uani 1 1 d . . .
H28A H 0.7514 1.1272 0.1162 0.063 Uiso 1 1 calc R . .
H28B H 0.7041 1.1737 0.1902 0.063 Uiso 1 1 calc R . .
C29 C 0.64771(14) 1.2833(2) 0.08286(15) 0.0643(6) Uani 1 1 d . . .
H29A H 0.6883 1.3684 0.0975 0.077 Uiso 1 1 calc R . .
H29B H 0.6429 1.2647 0.0243 0.077 Uiso 1 1 calc R . .


_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
N1 C9 1.412(2) . ?
N1 C6 1.422(2) . ?
N1 C11 1.433(2) . ?
C1 C5 1.339(2) . ?
C1 C2 1.467(2) . ?
C1 H1 0.9300 . ?
C2 C10 1.394(2) . ?
C2 C3 1.396(2) . ?
C3 C12 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C10 1.378(2) . ?
C4 C6 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C8 1.497(2) . ?
C5 C28 1.507(2) . ?
C6 C12 1.388(2) . ?
O1 C8 1.226(2) . ?
C7 C17 1.387(2) . ?
C7 C16 1.397(3) . ?
C7 C8 1.480(2) . ?
C9 C18 1.385(2) . ?
C9 C15 1.393(2) . ?
C10 H10 0.9300 . ?
C11 C14 1.384(2) . ?
C11 C13 1.388(2) . ?
C12 H12 0.9300 . ?
C13 C20 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C21 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C19 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C27 1.395(3) . ?
C16 C29 1.498(3) . ?
C17 C24 1.378(3) . ?
C17 H17 0.9300 . ?
C18 C23 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C26 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C26 1.361(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C27 1.373(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.520(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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
C9 N1 C6 121.09(14) . . ?
C9 N1 C11 120.15(14) . . ?
C6 N1 C11 116.89(13) . . ?
C5 C1 C2 130.40(16) . . ?
C5 C1 H1 114.8 . . ?
C2 C1 H1 114.8 . . ?
C10 C2 C3 116.75(15) . . ?
C10 C2 C1 124.41(16) . . ?
C3 C2 C1 118.80(15) . . ?
C12 C3 C2 122.17(16) . . ?
C12 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C10 C4 C6 120.93(16) . . ?
C10 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C1 C5 C8 117.34(15) . . ?
C1 C5 C28 126.11(15) . . ?
C8 C5 C28 116.55(15) . . ?
C12 C6 C4 118.43(16) . . ?
C12 C6 N1 122.16(16) . . ?
C4 C6 N1 119.40(15) . . ?
C17 C7 C16 119.41(17) . . ?
C17 C7 C8 120.36(18) . . ?
C16 C7 C8 120.22(16) . . ?
O1 C8 C7 120.58(16) . . ?
O1 C8 C5 121.41(16) . . ?
C7 C8 C5 118.00(16) . . ?
C18 C9 C15 118.32(16) . . ?
C18 C9 N1 121.32(16) . . ?
C15 C9 N1 120.36(16) . . ?
C4 C10 C2 121.48(16) . . ?
C4 C10 H10 119.3 . . ?
C2 C10 H10 119.3 . . ?
C14 C11 C13 118.57(16) . . ?
C14 C11 N1 120.33(15) . . ?
C13 C11 N1 121.09(16) . . ?
C3 C12 C6 120.15(17) . . ?
C3 C12 H12 119.9 . . ?
C6 C12 H12 119.9 . . ?
C20 C13 C11 120.26(18) . . ?
C20 C13 H13 119.9 . . ?
C11 C13 H13 119.9 . . ?
C21 C14 C11 120.85(17) . . ?
C21 C14 H14 119.6 . . ?
C11 C14 H14 119.6 . . ?
C19 C15 C9 119.99(19) . . ?
C19 C15 H15 120.0 . . ?
C9 C15 H15 120.0 . . ?
C27 C16 C7 118.57(18) . . ?
C27 C16 C29 122.27(18) . . ?
C7 C16 C29 119.15(16) . . ?
C24 C17 C7 121.0(2) . . ?
C24 C17 H17 119.5 . . ?
C7 C17 H17 119.5 . . ?
C23 C18 C9 120.64(18) . . ?
C23 C18 H18 119.7 . . ?
C9 C18 H18 119.7 . . ?
C26 C19 C15 121.0(2) . . ?
C26 C19 H19 119.5 . . ?
C15 C19 H19 119.5 . . ?
C22 C20 C13 120.45(17) . . ?
C22 C20 H20 119.8 . . ?
C13 C20 H20 119.8 . . ?
C22 C21 C14 120.12(19) . . ?
C22 C21 H21 119.9 . . ?
C14 C21 H21 119.9 . . ?
C21 C22 C20 119.73(18) . . ?
C21 C22 H22 120.1 . . ?
C20 C22 H22 120.1 . . ?
C26 C23 C18 121.14(19) . . ?
C26 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
C25 C24 C17 119.67(19) . . ?
C25 C24 H24 120.2 . . ?
C17 C24 H24 120.2 . . ?
C24 C25 C27 120.30(19) . . ?
C24 C25 H25 119.9 . . ?
C27 C25 H25 119.9 . . ?
C23 C26 C19 118.90(18) . . ?
C23 C26 H26 120.6 . . ?
C19 C26 H26 120.6 . . ?
C25 C27 C16 121.0(2) . . ?
C25 C27 H27 119.5 . . ?
C16 C27 H27 119.5 . . ?
C5 C28 C29 111.71(15) . . ?
C5 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
C5 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C16 C29 C28 111.50(16) . . ?
C16 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
C16 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?

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
C5 C1 C2 C10 26.7(3) . . . . ?
C5 C1 C2 C3 -155.64(19) . . . . ?
C10 C2 C3 C12 -2.7(3) . . . . ?
C1 C2 C3 C12 179.45(16) . . . . ?
C2 C1 C5 C8 -176.99(17) . . . . ?
C2 C1 C5 C28 3.6(3) . . . . ?
C10 C4 C6 C12 -1.7(3) . . . . ?
C10 C4 C6 N1 177.33(15) . . . . ?
C9 N1 C6 C12 -41.1(2) . . . . ?
C11 N1 C6 C12 123.39(19) . . . . ?
C9 N1 C6 C4 139.99(17) . . . . ?
C11 N1 C6 C4 -55.6(2) . . . . ?
C17 C7 C8 O1 19.7(3) . . . . ?
C16 C7 C8 O1 -161.15(17) . . . . ?
C17 C7 C8 C5 -159.00(17) . . . . ?
C16 C7 C8 C5 20.1(2) . . . . ?
C1 C5 C8 O1 1.6(3) . . . . ?
C28 C5 C8 O1 -178.92(17) . . . . ?
C1 C5 C8 C7 -179.67(16) . . . . ?
C28 C5 C8 C7 -0.2(2) . . . . ?
C6 N1 C9 C18 147.52(17) . . . . ?
C11 N1 C9 C18 -16.4(2) . . . . ?
C6 N1 C9 C15 -33.3(2) . . . . ?
C11 N1 C9 C15 162.78(16) . . . . ?
C6 C4 C10 C2 -0.5(3) . . . . ?
C3 C2 C10 C4 2.7(3) . . . . ?
C1 C2 C10 C4 -179.61(16) . . . . ?
C9 N1 C11 C14 119.70(18) . . . . ?
C6 N1 C11 C14 -44.9(2) . . . . ?
C9 N1 C11 C13 -59.7(2) . . . . ?
C6 N1 C11 C13 135.68(17) . . . . ?
C2 C3 C12 C6 0.6(3) . . . . ?
C4 C6 C12 C3 1.7(3) . . . . ?
N1 C6 C12 C3 -177.31(16) . . . . ?
C14 C11 C13 C20 -0.7(3) . . . . ?
N1 C11 C13 C20 178.70(16) . . . . ?
C13 C11 C14 C21 0.2(3) . . . . ?
N1 C11 C14 C21 -179.19(17) . . . . ?
C18 C9 C15 C19 -0.4(3) . . . . ?
N1 C9 C15 C19 -179.64(16) . . . . ?
C17 C7 C16 C27 -1.5(3) . . . . ?
C8 C7 C16 C27 179.33(17) . . . . ?
C17 C7 C16 C29 178.61(18) . . . . ?
C8 C7 C16 C29 -0.5(3) . . . . ?
C16 C7 C17 C24 0.3(3) . . . . ?
C8 C7 C17 C24 179.50(17) . . . . ?
C15 C9 C18 C23 -0.4(3) . . . . ?
N1 C9 C18 C23 178.87(16) . . . . ?
C9 C15 C19 C26 0.7(3) . . . . ?
C11 C13 C20 C22 0.1(3) . . . . ?
C11 C14 C21 C22 0.8(3) . . . . ?
C14 C21 C22 C20 -1.4(3) . . . . ?
C13 C20 C22 C21 0.9(3) . . . . ?
C9 C18 C23 C26 0.9(3) . . . . ?
C7 C17 C24 C25 1.2(3) . . . . ?
C17 C24 C25 C27 -1.5(3) . . . . ?
C18 C23 C26 C19 -0.6(3) . . . . ?
C15 C19 C26 C23 -0.2(3) . . . . ?
C24 C25 C27 C16 0.3(3) . . . . ?
C7 C16 C27 C25 1.2(3) . . . . ?
C29 C16 C27 C25 -178.9(2) . . . . ?
C1 C5 C28 C29 142.95(19) . . . . ?
C8 C5 C28 C29 -36.4(2) . . . . ?
C27 C16 C29 C28 143.13(19) . . . . ?
C7 C16 C29 C28 -37.0(3) . . . . ?
C5 C28 C29 C16 54.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_d_2
_database_code_depnum_ccdc_archive 'CCDC 1854441'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H40 Br2 N2 O2'
_chemical_formula_weight         932.72

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2406(8)
_cell_length_b                   11.0561(8)
_cell_length_c                   20.0822(12)
_cell_angle_alpha                104.423(6)
_cell_angle_beta                 92.104(5)
_cell_angle_gamma                98.285(6)
_cell_volume                     2172.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2270
_cell_measurement_theta_min      3.2369
_cell_measurement_theta_max      29.3372

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14547
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         25.35
_reflns_number_total             7938
_reflns_number_gt                4365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.6933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7938
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.38443(6) 0.28275(6) 0.69251(3) 0.0839(2) Uani 1 1 d . . .
Br02 Br 0.13093(6) 1.20492(6) 0.29620(3) 0.0905(3) Uani 1 1 d . . .
O003 O 0.5242(3) 0.7471(2) 0.51448(13) 0.0398(7) Uani 1 1 d . . .
O004 O -0.0296(3) 0.7582(2) 0.48343(13) 0.0405(7) Uani 1 1 d . . .
N005 N 0.5284(4) 0.9510(3) 0.81455(17) 0.0509(10) Uani 1 1 d . . .
N006 N -0.0296(4) 0.5208(3) 0.18174(17) 0.0517(10) Uani 1 1 d . . .
C007 C 0.2675(4) 0.7263(3) 0.44378(18) 0.0290(9) Uani 1 1 d . . .
H007 H 0.3554 0.7626 0.4338 0.035 Uiso 1 1 calc R . .
C008 C 0.4397(4) 0.5862(3) 0.57050(18) 0.0304(9) Uani 1 1 d . . .
C009 C 0.1919(4) 0.6609(3) 0.37588(18) 0.0312(9) Uani 1 1 d . . .
C00A C 0.2700(4) 0.9706(3) 0.49139(19) 0.0316(9) Uani 1 1 d . . .
H00A H 0.2699 1.0314 0.5355 0.038 Uiso 1 1 calc R . .
H00B H 0.3601 0.9721 0.4778 0.038 Uiso 1 1 calc R . .
C00B C 0.3202(4) 0.5044(3) 0.56037(18) 0.0329(9) Uani 1 1 d . . .
C00C C 0.2875(4) 0.6648(3) 0.50439(18) 0.0296(9) Uani 1 1 d . . .
C00D C 0.0631(4) 0.8292(4) 0.47108(18) 0.0311(9) Uani 1 1 d . . .
C00E C 0.4337(4) 0.6758(3) 0.52756(18) 0.0304(9) Uani 1 1 d . . .
C00F C 0.2079(4) 0.8373(3) 0.49442(17) 0.0280(8) Uani 1 1 d . . .
C00G C 0.2990(4) 0.8386(3) 0.62313(18) 0.0296(9) Uani 1 1 d . . .
C00H C 0.1804(4) 0.9972(3) 0.43714(19) 0.0318(9) Uani 1 1 d . . .
C00I C 0.3010(4) 0.4124(4) 0.5968(2) 0.0400(10) Uani 1 1 d . . .
H00I H 0.2218 0.3565 0.5911 0.048 Uiso 1 1 calc R . .
C00J C 0.0595(4) 0.9174(3) 0.42683(18) 0.0314(9) Uani 1 1 d . . .
C00K C 0.2256(4) 0.7749(3) 0.55488(18) 0.0292(9) Uani 1 1 d . . .
H00K H 0.1373 0.7379 0.5639 0.035 Uiso 1 1 calc R . .
C00L C 0.5242(4) 0.4887(4) 0.6524(2) 0.0393(10) Uani 1 1 d . . .
H00L H 0.5908 0.4822 0.6835 0.047 Uiso 1 1 calc R . .
C00M C 0.4154(4) 0.9259(4) 0.63361(19) 0.0362(10) Uani 1 1 d . . .
H00M H 0.4445 0.9587 0.5974 0.043 Uiso 1 1 calc R . .
C00N C 0.2275(4) 0.5310(3) 0.50783(19) 0.0330(9) Uani 1 1 d . . .
H00C H 0.1383 0.5289 0.5227 0.040 Uiso 1 1 calc R . .
H00D H 0.2258 0.4705 0.4634 0.040 Uiso 1 1 calc R . .
C00O C 0.5423(4) 0.5789(4) 0.61584(19) 0.0362(9) Uani 1 1 d . . .
H00O H 0.6218 0.6341 0.6214 0.043 Uiso 1 1 calc R . .
C00P C 0.4478(4) 0.9179(4) 0.75163(19) 0.0393(10) Uani 1 1 d . . .
C00Q C 0.4040(4) 0.4072(4) 0.6419(2) 0.0421(10) Uani 1 1 d . . .
C00R C 0.0816(4) 0.5688(4) 0.36553(19) 0.0392(10) Uani 1 1 d . . .
H00R H 0.0547 0.5362 0.4022 0.047 Uiso 1 1 calc R . .
C00S C 0.2573(4) 0.7965(4) 0.68000(19) 0.0377(10) Uani 1 1 d . . .
H00S H 0.1788 0.7400 0.6753 0.045 Uiso 1 1 calc R . .
C00T C 0.4885(4) 0.9648(4) 0.69660(19) 0.0398(10) Uani 1 1 d . . .
H00T H 0.5658 1.0231 0.7021 0.048 Uiso 1 1 calc R . .
C00U C 0.2033(4) 1.0858(4) 0.3991(2) 0.0407(10) Uani 1 1 d . . .
H00U H 0.2829 1.1412 0.4053 0.049 Uiso 1 1 calc R . .
C00V C -0.0402(4) 0.9229(4) 0.37930(19) 0.0363(9) Uani 1 1 d . . .
H00V H -0.1206 0.8689 0.3735 0.044 Uiso 1 1 calc R . .
C00W C 0.0098(4) 0.5232(4) 0.3021(2) 0.0447(11) Uani 1 1 d . . .
H00W H -0.0642 0.4612 0.2971 0.054 Uiso 1 1 calc R . .
C00X C 0.1030(4) 1.0889(4) 0.3515(2) 0.0431(10) Uani 1 1 d . . .
C00Y C -0.0174(4) 1.0091(4) 0.3413(2) 0.0429(10) Uani 1 1 d . . .
H00Y H -0.0821 1.0144 0.3089 0.052 Uiso 1 1 calc R . .
C00Z C 0.2286(4) 0.7050(4) 0.3183(2) 0.0412(10) Uani 1 1 d . . .
H00Z H 0.3024 0.7672 0.3231 0.049 Uiso 1 1 calc R . .
C010 C 0.0467(4) 0.5686(4) 0.24655(19) 0.0429(11) Uani 1 1 d . . .
C011 C 0.3297(5) 0.8367(4) 0.7435(2) 0.0452(11) Uani 1 1 d . . .
H011 H 0.2983 0.8085 0.7807 0.054 Uiso 1 1 calc R . .
C012 C 0.5408(4) 0.8585(4) 0.8512(2) 0.0446(11) Uani 1 1 d . . .
C013 C -0.0712(4) 0.6053(4) 0.1461(2) 0.0448(11) Uani 1 1 d . . .
C014 C 0.5783(5) 1.0803(4) 0.8459(2) 0.0470(11) Uani 1 1 d . . .
C015 C 0.1585(5) 0.6589(4) 0.2552(2) 0.0459(11) Uani 1 1 d . . .
H015 H 0.1867 0.6888 0.2179 0.055 Uiso 1 1 calc R . .
C016 C -0.0371(5) 0.3892(4) 0.1489(2) 0.0519(12) Uani 1 1 d . . .
C017 C 0.5005(5) 1.1727(4) 0.8470(2) 0.0573(13) Uani 1 1 d . . .
H017 H 0.4149 1.1503 0.8261 0.069 Uiso 1 1 calc R . .
C018 C -0.0937(5) 0.5724(4) 0.0751(2) 0.0528(12) Uani 1 1 d . . .
H018 H -0.0822 0.4922 0.0500 0.063 Uiso 1 1 calc R . .
C019 C 0.7064(5) 1.1153(5) 0.8768(2) 0.0641(14) Uani 1 1 d . . .
H019 H 0.7613 1.0547 0.8753 0.077 Uiso 1 1 calc R . .
C01A C 0.0743(6) 0.3339(5) 0.1477(2) 0.0692(15) Uani 1 1 d . . .
H01A H 0.1538 0.3824 0.1687 0.083 Uiso 1 1 calc R . .
C01B C -0.0889(5) 0.7263(5) 0.1823(2) 0.0616(14) Uani 1 1 d . . .
H01B H -0.0747 0.7508 0.2301 0.074 Uiso 1 1 calc R . .
C01C C 0.5457(5) 0.8880(4) 0.9223(2) 0.0603(14) Uani 1 1 d . . .
H01C H 0.5441 0.9709 0.9470 0.072 Uiso 1 1 calc R . .
C01D C 0.5451(5) 0.7348(4) 0.8161(2) 0.0611(14) Uani 1 1 d . . .
H01D H 0.5438 0.7130 0.7683 0.073 Uiso 1 1 calc R . .
C01E C -0.1329(5) 0.6559(5) 0.0407(3) 0.0705(15) Uani 1 1 d . . .
H01E H -0.1482 0.6316 -0.0070 0.085 Uiso 1 1 calc R . .
C01F C -0.1559(6) 0.3174(6) 0.1184(3) 0.0752(16) Uani 1 1 d . . .
H01F H -0.2326 0.3536 0.1199 0.090 Uiso 1 1 calc R . .
C01G C 0.5511(6) 0.6433(5) 0.8515(3) 0.0728(16) Uani 1 1 d . . .
H01G H 0.5538 0.5605 0.8271 0.087 Uiso 1 1 calc R . .
C01H C 0.5480(7) 1.2972(5) 0.8786(3) 0.0755(17) Uani 1 1 d . . .
H01H H 0.4953 1.3591 0.8787 0.091 Uiso 1 1 calc R . .
C01I C 0.5531(6) 0.6728(5) 0.9215(3) 0.0787(18) Uani 1 1 d . . .
H01I H 0.5546 0.6101 0.9448 0.094 Uiso 1 1 calc R . .
C01J C 0.7518(6) 1.2407(6) 0.9099(3) 0.0815(18) Uani 1 1 d . . .
H01J H 0.8365 1.2638 0.9319 0.098 Uiso 1 1 calc R . .
C01K C 0.5530(6) 0.7955(5) 0.9574(2) 0.0819(19) Uani 1 1 d . . .
H01K H 0.5577 0.8169 1.0053 0.098 Uiso 1 1 calc R . .
C01L C -0.1490(6) 0.7740(6) 0.0765(3) 0.0808(17) Uani 1 1 d . . .
H01L H -0.1747 0.8308 0.0533 0.097 Uiso 1 1 calc R . .
C01M C 0.6747(8) 1.3299(6) 0.9104(3) 0.089(2) Uani 1 1 d . . .
H01M H 0.7070 1.4140 0.9324 0.107 Uiso 1 1 calc R . .
C01N C -0.1271(6) 0.8091(5) 0.1476(3) 0.0802(17) Uani 1 1 d . . .
H01N H -0.1384 0.8897 0.1721 0.096 Uiso 1 1 calc R . .
C01O C -0.1595(9) 0.1891(7) 0.0852(3) 0.105(3) Uani 1 1 d . . .
H01O H -0.2379 0.1398 0.0633 0.126 Uiso 1 1 calc R . .
C01P C 0.0705(9) 0.2081(7) 0.1161(3) 0.096(2) Uani 1 1 d . . .
H01P H 0.1470 0.1718 0.1156 0.116 Uiso 1 1 calc R . .
C01Q C -0.0446(12) 0.1373(7) 0.0856(4) 0.114(3) Uani 1 1 d . . .
H01Q H -0.0467 0.0519 0.0644 0.137 Uiso 1 1 calc R . .


_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
Br01 C00Q 1.897(4) . ?
Br02 C00X 1.894(4) . ?
O003 C00E 1.208(4) . ?
O004 C00D 1.216(4) . ?
N005 C012 1.418(5) . ?
N005 C014 1.420(5) . ?
N005 C00P 1.421(5) . ?
N006 C013 1.411(5) . ?
N006 C016 1.430(6) . ?
N006 C010 1.431(5) . ?
C007 C009 1.501(5) . ?
C007 C00C 1.555(5) . ?
C007 C00F 1.598(5) . ?
C007 H007 0.9800 . ?
C008 C00B 1.388(5) . ?
C008 C00O 1.389(5) . ?
C008 C00E 1.472(5) . ?
C009 C00R 1.379(5) . ?
C009 C00Z 1.405(5) . ?
C00A C00H 1.510(5) . ?
C00A C00F 1.536(5) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00B C00I 1.390(5) . ?
C00B C00N 1.505(5) . ?
C00C C00E 1.530(5) . ?
C00C C00N 1.537(5) . ?
C00C C00K 1.602(5) . ?
C00D C00J 1.477(5) . ?
C00D C00F 1.522(5) . ?
C00F C00K 1.556(5) . ?
C00G C00M 1.395(5) . ?
C00G C00S 1.395(5) . ?
C00G C00K 1.493(5) . ?
C00H C00U 1.384(5) . ?
C00H C00J 1.390(5) . ?
C00I C00Q 1.382(6) . ?
C00I H00I 0.9300 . ?
C00J C00V 1.390(5) . ?
C00K H00K 0.9800 . ?
C00L C00O 1.374(5) . ?
C00L C00Q 1.392(6) . ?
C00L H00L 0.9300 . ?
C00M C00T 1.383(5) . ?
C00M H00M 0.9300 . ?
C00N H00C 0.9700 . ?
C00N H00D 0.9700 . ?
C00O H00O 0.9300 . ?
C00P C011 1.376(6) . ?
C00P C00T 1.386(5) . ?
C00R C00W 1.386(6) . ?
C00R H00R 0.9300 . ?
C00S C011 1.387(6) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U C00X 1.388(6) . ?
C00U H00U 0.9300 . ?
C00V C00Y 1.362(5) . ?
C00V H00V 0.9300 . ?
C00W C010 1.377(5) . ?
C00W H00W 0.9300 . ?
C00X C00Y 1.385(6) . ?
C00Y H00Y 0.9300 . ?
C00Z C015 1.374(6) . ?
C00Z H00Z 0.9300 . ?
C010 C015 1.382(6) . ?
C011 H011 0.9300 . ?
C012 C01C 1.380(6) . ?
C012 C01D 1.381(6) . ?
C013 C018 1.384(6) . ?
C013 C01B 1.394(6) . ?
C014 C017 1.380(6) . ?
C014 C019 1.390(7) . ?
C015 H015 0.9300 . ?
C016 C01A 1.368(7) . ?
C016 C01F 1.382(7) . ?
C017 C01H 1.373(7) . ?
C017 H017 0.9300 . ?
C018 C01E 1.375(6) . ?
C018 H018 0.9300 . ?
C019 C01J 1.383(7) . ?
C019 H019 0.9300 . ?
C01A C01P 1.372(8) . ?
C01A H01A 0.9300 . ?
C01B C01N 1.371(7) . ?
C01B H01B 0.9300 . ?
C01C C01K 1.388(6) . ?
C01C H01C 0.9300 . ?
C01D C01G 1.379(6) . ?
C01D H01D 0.9300 . ?
C01E C01L 1.362(7) . ?
C01E H01E 0.9300 . ?
C01F C01O 1.403(8) . ?
C01F H01F 0.9300 . ?
C01G C01I 1.361(7) . ?
C01G H01G 0.9300 . ?
C01H C01M 1.383(9) . ?
C01H H01H 0.9300 . ?
C01I C01K 1.368(7) . ?
C01I H01I 0.9300 . ?
C01J C01M 1.347(9) . ?
C01J H01J 0.9300 . ?
C01K H01K 0.9300 . ?
C01L C01N 1.384(7) . ?
C01L H01L 0.9300 . ?
C01M H01M 0.9300 . ?
C01N H01N 0.9300 . ?
C01O C01Q 1.381(10) . ?
C01O H01O 0.9300 . ?
C01P C01Q 1.349(10) . ?
C01P H01P 0.9300 . ?
C01Q H01Q 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
C012 N005 C014 119.9(4) . . ?
C012 N005 C00P 119.8(4) . . ?
C014 N005 C00P 119.5(3) . . ?
C013 N006 C016 121.5(4) . . ?
C013 N006 C010 120.0(4) . . ?
C016 N006 C010 117.2(4) . . ?
C009 C007 C00C 125.3(3) . . ?
C009 C007 C00F 118.1(3) . . ?
C00C C007 C00F 90.0(2) . . ?
C009 C007 H007 107.2 . . ?
C00C C007 H007 107.2 . . ?
C00F C007 H007 107.2 . . ?
C00B C008 C00O 122.1(3) . . ?
C00B C008 C00E 108.9(3) . . ?
C00O C008 C00E 129.0(4) . . ?
C00R C009 C00Z 116.4(4) . . ?
C00R C009 C007 126.0(3) . . ?
C00Z C009 C007 117.4(4) . . ?
C00H C00A C00F 102.7(3) . . ?
C00H C00A H00A 111.2 . . ?
C00F C00A H00A 111.2 . . ?
C00H C00A H00B 111.2 . . ?
C00F C00A H00B 111.2 . . ?
H00A C00A H00B 109.1 . . ?
C008 C00B C00I 119.6(4) . . ?
C008 C00B C00N 111.4(3) . . ?
C00I C00B C00N 129.1(4) . . ?
C00E C00C C00N 103.8(3) . . ?
C00E C00C C007 112.4(3) . . ?
C00N C00C C007 126.8(3) . . ?
C00E C00C C00K 109.0(3) . . ?
C00N C00C C00K 113.7(3) . . ?
C007 C00C C00K 90.1(2) . . ?
O004 C00D C00J 127.2(4) . . ?
O004 C00D C00F 126.2(3) . . ?
C00J C00D C00F 106.5(3) . . ?
O003 C00E C008 127.7(4) . . ?
O003 C00E C00C 126.1(3) . . ?
C008 C00E C00C 106.1(3) . . ?
C00D C00F C00A 103.5(3) . . ?
C00D C00F C00K 112.5(3) . . ?
C00A C00F C00K 126.9(3) . . ?
C00D C00F C007 108.8(3) . . ?
C00A C00F C007 113.9(3) . . ?
C00K C00F C007 90.2(2) . . ?
C00M C00G C00S 116.7(4) . . ?
C00M C00G C00K 125.4(3) . . ?
C00S C00G C00K 117.4(3) . . ?
C00U C00H C00J 119.4(4) . . ?
C00U C00H C00A 129.5(4) . . ?
C00J C00H C00A 111.2(3) . . ?
C00Q C00I C00B 117.4(4) . . ?
C00Q C00I H00I 121.3 . . ?
C00B C00I H00I 121.3 . . ?
C00H C00J C00V 122.3(3) . . ?
C00H C00J C00D 108.4(3) . . ?
C00V C00J C00D 129.3(4) . . ?
C00G C00K C00F 125.6(3) . . ?
C00G C00K C00C 117.7(3) . . ?
C00F C00K C00C 89.8(2) . . ?
C00G C00K H00K 107.3 . . ?
C00F C00K H00K 107.3 . . ?
C00C C00K H00K 107.3 . . ?
C00O C00L C00Q 118.5(4) . . ?
C00O C00L H00L 120.7 . . ?
C00Q C00L H00L 120.7 . . ?
C00T C00M C00G 121.5(3) . . ?
C00T C00M H00M 119.3 . . ?
C00G C00M H00M 119.3 . . ?
C00B C00N C00C 102.9(3) . . ?
C00B C00N H00C 111.2 . . ?
C00C C00N H00C 111.2 . . ?
C00B C00N H00D 111.2 . . ?
C00C C00N H00D 111.2 . . ?
H00C C00N H00D 109.1 . . ?
C00L C00O C008 118.9(4) . . ?
C00L C00O H00O 120.6 . . ?
C008 C00O H00O 120.6 . . ?
C011 C00P C00T 118.7(4) . . ?
C011 C00P N005 120.9(3) . . ?
C00T C00P N005 120.3(4) . . ?
C00I C00Q C00L 123.5(4) . . ?
C00I C00Q Br01 119.4(3) . . ?
C00L C00Q Br01 117.1(3) . . ?
C009 C00R C00W 121.9(4) . . ?
C009 C00R H00R 119.0 . . ?
C00W C00R H00R 119.0 . . ?
C011 C00S C00G 121.7(4) . . ?
C011 C00S H00S 119.1 . . ?
C00G C00S H00S 119.1 . . ?
C00M C00T C00P 120.7(4) . . ?
C00M C00T H00T 119.6 . . ?
C00P C00T H00T 119.6 . . ?
C00H C00U C00X 117.5(4) . . ?
C00H C00U H00U 121.3 . . ?
C00X C00U H00U 121.3 . . ?
C00Y C00V C00J 118.5(4) . . ?
C00Y C00V H00V 120.8 . . ?
C00J C00V H00V 120.8 . . ?
C010 C00W C00R 120.9(4) . . ?
C010 C00W H00W 119.6 . . ?
C00R C00W H00W 119.6 . . ?
C00Y C00X C00U 123.0(4) . . ?
C00Y C00X Br02 117.8(3) . . ?
C00U C00X Br02 119.3(3) . . ?
C00V C00Y C00X 119.4(4) . . ?
C00V C00Y H00Y 120.3 . . ?
C00X C00Y H00Y 120.3 . . ?
C015 C00Z C009 121.9(4) . . ?
C015 C00Z H00Z 119.1 . . ?
C009 C00Z H00Z 119.1 . . ?
C00W C010 C015 118.3(4) . . ?
C00W C010 N006 119.8(4) . . ?
C015 C010 N006 121.8(4) . . ?
C00P C011 C00S 120.5(3) . . ?
C00P C011 H011 119.8 . . ?
C00S C011 H011 119.8 . . ?
C01C C012 C01D 118.2(4) . . ?
C01C C012 N005 121.4(4) . . ?
C01D C012 N005 120.4(4) . . ?
C018 C013 C01B 118.1(4) . . ?
C018 C013 N006 121.7(4) . . ?
C01B C013 N006 120.2(4) . . ?
C017 C014 C019 118.9(5) . . ?
C017 C014 N005 120.9(5) . . ?
C019 C014 N005 120.2(4) . . ?
C00Z C015 C010 120.6(4) . . ?
C00Z C015 H015 119.7 . . ?
C010 C015 H015 119.7 . . ?
C01A C016 C01F 119.8(5) . . ?
C01A C016 N006 119.7(5) . . ?
C01F C016 N006 120.5(5) . . ?
C01H C017 C014 120.8(5) . . ?
C01H C017 H017 119.6 . . ?
C014 C017 H017 119.6 . . ?
C01E C018 C013 121.3(4) . . ?
C01E C018 H018 119.3 . . ?
C013 C018 H018 119.3 . . ?
C01J C019 C014 119.6(5) . . ?
C01J C019 H019 120.2 . . ?
C014 C019 H019 120.2 . . ?
C016 C01A C01P 121.0(6) . . ?
C016 C01A H01A 119.5 . . ?
C01P C01A H01A 119.5 . . ?
C01N C01B C013 120.2(4) . . ?
C01N C01B H01B 119.9 . . ?
C013 C01B H01B 119.9 . . ?
C012 C01C C01K 120.8(4) . . ?
C012 C01C H01C 119.6 . . ?
C01K C01C H01C 119.6 . . ?
C01G C01D C012 120.6(4) . . ?
C01G C01D H01D 119.7 . . ?
C012 C01D H01D 119.7 . . ?
C01L C01E C018 120.1(5) . . ?
C01L C01E H01E 120.0 . . ?
C018 C01E H01E 120.0 . . ?
C016 C01F C01O 119.2(6) . . ?
C016 C01F H01F 120.4 . . ?
C01O C01F H01F 120.4 . . ?
C01I C01G C01D 120.8(5) . . ?
C01I C01G H01G 119.6 . . ?
C01D C01G H01G 119.6 . . ?
C017 C01H C01M 119.5(6) . . ?
C017 C01H H01H 120.3 . . ?
C01M C01H H01H 120.3 . . ?
C01G C01I C01K 119.5(5) . . ?
C01G C01I H01I 120.2 . . ?
C01K C01I H01I 120.2 . . ?
C01M C01J C019 120.7(6) . . ?
C01M C01J H01J 119.6 . . ?
C019 C01J H01J 119.6 . . ?
C01I C01K C01C 120.0(4) . . ?
C01I C01K H01K 120.0 . . ?
C01C C01K H01K 120.0 . . ?
C01E C01L C01N 119.7(5) . . ?
C01E C01L H01L 120.2 . . ?
C01N C01L H01L 120.2 . . ?
C01J C01M C01H 120.5(6) . . ?
C01J C01M H01M 119.8 . . ?
C01H C01M H01M 119.8 . . ?
C01B C01N C01L 120.6(5) . . ?
C01B C01N H01N 119.7 . . ?
C01L C01N H01N 119.7 . . ?
C01Q C01O C01F 119.0(8) . . ?
C01Q C01O H01O 120.5 . . ?
C01F C01O H01O 120.5 . . ?
C01Q C01P C01A 119.8(7) . . ?
C01Q C01P H01P 120.1 . . ?
C01A C01P H01P 120.1 . . ?
C01P C01Q C01O 121.2(7) . . ?
C01P C01Q H01Q 119.4 . . ?
C01O C01Q H01Q 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1854439'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8384(5)
_cell_length_b                   9.7004(11)
_cell_length_c                   11.9861(10)
_cell_angle_alpha                95.783(8)
_cell_angle_beta                 104.947(7)
_cell_angle_gamma                95.234(7)
_cell_volume                     758.58(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1393
_cell_measurement_theta_min      3.1001
_cell_measurement_theta_max      29.2806

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4182
_exptl_absorpt_correction_T_max  0.5509
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4604
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2665
_reflns_number_gt                1814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2665
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.47399(6) -0.33895(6) 0.66800(4) 0.0955(3) Uani 1 1 d . . .
O O 0.5883(4) -0.1422(3) 0.3197(2) 0.0804(8) Uani 1 1 d . . .
C2 C 1.2503(5) -0.2752(4) 0.5649(3) 0.0587(9) Uani 1 1 d . . .
C3 C 1.0614(5) 0.1504(4) 0.1128(3) 0.0548(9) Uani 1 1 d . . .
H3 H 1.1635 0.1176 0.1674 0.066 Uiso 1 1 calc R . .
C4 C 1.1186(5) -0.1409(4) 0.4161(2) 0.0479(8) Uani 1 1 d . . .
C5 C 0.8581(5) 0.1163(4) 0.1117(3) 0.0504(8) Uani 1 1 d . . .
C6 C 1.1136(4) -0.0444(4) 0.3244(3) 0.0486(8) Uani 1 1 d . . .
H6A H 1.1853 0.0472 0.3586 0.058 Uiso 1 1 calc R . .
H6B H 1.1739 -0.0822 0.2648 0.058 Uiso 1 1 calc R . .
C7 C 1.1143(5) 0.2313(4) 0.0352(3) 0.0568(9) Uani 1 1 d . . .
H7 H 1.2515 0.2530 0.0394 0.068 Uiso 1 1 calc R . .
N N 1.0207(5) 0.3612(3) -0.1281(3) 0.0723(9) Uani 1 1 d . . .
C9 C 0.9679(5) 0.2817(4) -0.0499(3) 0.0548(9) Uani 1 1 d . . .
C10 C 1.2860(5) -0.1847(4) 0.4891(3) 0.0560(9) Uani 1 1 d . . .
H10 H 1.4179 -0.1543 0.4871 0.067 Uiso 1 1 calc R . .
C11 C 0.8889(5) -0.0374(4) 0.2750(3) 0.0499(8) Uani 1 1 d . . .
C12 C 0.7737(5) -0.1240(4) 0.3360(3) 0.0571(9) Uani 1 1 d . . .
C13 C 0.7891(5) 0.0297(4) 0.1890(3) 0.0548(9) Uani 1 1 d . . .
H13 H 0.6484 0.0183 0.1767 0.066 Uiso 1 1 calc R . .
C14 C 0.7650(5) 0.2453(4) -0.0527(3) 0.0622(10) Uani 1 1 d . . .
H14 H 0.6625 0.2749 -0.1092 0.075 Uiso 1 1 calc R . .
C15 C 0.9236(5) -0.1874(4) 0.4207(3) 0.0522(8) Uani 1 1 d . . .
C16 C 0.7139(5) 0.1668(4) 0.0263(3) 0.0611(10) Uani 1 1 d . . .
H16 H 0.5767 0.1463 0.0227 0.073 Uiso 1 1 calc R . .
C17 C 1.0572(6) -0.3240(4) 0.5690(3) 0.0659(10) Uani 1 1 d . . .
H17 H 1.0395 -0.3865 0.6206 0.079 Uiso 1 1 calc R . .
C18 C 0.8918(5) -0.2803(4) 0.4968(3) 0.0628(10) Uani 1 1 d . . .
H18 H 0.7603 -0.3121 0.4987 0.075 Uiso 1 1 calc R . .
C19 C 1.2302(6) 0.4072(5) -0.1213(3) 0.0816(12) Uani 1 1 d . . .
H19A H 1.2909 0.4671 -0.0495 0.122 Uiso 1 1 calc R . .
H19B H 1.2360 0.4575 -0.1856 0.122 Uiso 1 1 calc R . .
H19C H 1.3034 0.3276 -0.1242 0.122 Uiso 1 1 calc R . .
C21 C 0.8690(7) 0.4246(5) -0.2087(3) 0.0855(13) Uani 1 1 d . . .
H21A H 0.7497 0.3581 -0.2411 0.128 Uiso 1 1 calc R . .
H21B H 0.9237 0.4527 -0.2702 0.128 Uiso 1 1 calc R . .
H21C H 0.8331 0.5047 -0.1681 0.128 Uiso 1 1 calc R . .


_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 C2 1.898(3) . ?
O C12 1.225(4) . ?
C2 C10 1.375(5) . ?
C2 C17 1.377(5) . ?
C3 C7 1.371(4) . ?
C3 C5 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C10 1.380(4) . ?
C4 C15 1.385(4) . ?
C4 C6 1.510(4) . ?
C5 C16 1.389(4) . ?
C5 C13 1.447(4) . ?
C6 C11 1.508(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.395(4) . ?
C7 H7 0.9300 . ?
N C9 1.368(4) . ?
N C19 1.440(5) . ?
N C21 1.451(4) . ?
C9 C14 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C13 1.344(4) . ?
C11 C12 1.470(5) . ?
C12 C15 1.470(5) . ?
C13 H13 0.9300 . ?
C14 C16 1.366(5) . ?
C14 H14 0.9300 . ?
C15 C18 1.388(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C2 C17 122.8(3) . . ?
C10 C2 Br1 119.5(3) . . ?
C17 C2 Br1 117.6(3) . . ?
C7 C3 C5 121.6(3) . . ?
C7 C3 H3 119.2 . . ?
C5 C3 H3 119.2 . . ?
C10 C4 C15 120.3(3) . . ?
C10 C4 C6 128.4(3) . . ?
C15 C4 C6 111.2(3) . . ?
C16 C5 C3 116.0(3) . . ?
C16 C5 C13 118.9(3) . . ?
C3 C5 C13 125.1(3) . . ?
C11 C6 C4 103.2(3) . . ?
C11 C6 H6A 111.1 . . ?
C4 C6 H6A 111.1 . . ?
C11 C6 H6B 111.1 . . ?
C4 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C3 C7 C9 121.8(3) . . ?
C3 C7 H7 119.1 . . ?
C9 C7 H7 119.1 . . ?
C9 N C19 122.0(3) . . ?
C9 N C21 121.2(3) . . ?
C19 N C21 115.9(3) . . ?
N C9 C14 121.6(3) . . ?
N C9 C7 121.7(3) . . ?
C14 C9 C7 116.7(3) . . ?
C2 C10 C4 117.4(3) . . ?
C2 C10 H10 121.3 . . ?
C4 C10 H10 121.3 . . ?
C13 C11 C12 119.9(3) . . ?
C13 C11 C6 131.1(3) . . ?
C12 C11 C6 109.0(3) . . ?
O C12 C11 127.3(3) . . ?
O C12 C15 125.8(3) . . ?
C11 C12 C15 106.9(3) . . ?
C11 C13 C5 132.5(3) . . ?
C11 C13 H13 113.7 . . ?
C5 C13 H13 113.7 . . ?
C16 C14 C9 121.1(3) . . ?
C16 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C4 C15 C18 121.1(3) . . ?
C4 C15 C12 109.6(3) . . ?
C18 C15 C12 129.3(3) . . ?
C14 C16 C5 122.8(3) . . ?
C14 C16 H16 118.6 . . ?
C5 C16 H16 118.6 . . ?
C18 C17 C2 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C2 C17 H17 120.2 . . ?
C17 C18 C15 118.7(3) . . ?
C17 C18 H18 120.7 . . ?
C15 C18 H18 120.7 . . ?
N C19 H19A 109.5 . . ?
N C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N C21 H21A 109.5 . . ?
N C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C3 C5 C16 1.2(5) . . . . ?
C7 C3 C5 C13 178.8(3) . . . . ?
C10 C4 C6 C11 179.9(3) . . . . ?
C15 C4 C6 C11 0.6(4) . . . . ?
C5 C3 C7 C9 -1.0(6) . . . . ?
C19 N C9 C14 175.8(4) . . . . ?
C21 N C9 C14 7.3(6) . . . . ?
C19 N C9 C7 -5.3(6) . . . . ?
C21 N C9 C7 -173.8(4) . . . . ?
C3 C7 C9 N -179.3(3) . . . . ?
C3 C7 C9 C14 -0.4(5) . . . . ?
C17 C2 C10 C4 1.0(6) . . . . ?
Br1 C2 C10 C4 -179.8(2) . . . . ?
C15 C4 C10 C2 0.1(5) . . . . ?
C6 C4 C10 C2 -179.1(3) . . . . ?
C4 C6 C11 C13 -178.4(3) . . . . ?
C4 C6 C11 C12 0.5(4) . . . . ?
C13 C11 C12 O -1.6(6) . . . . ?
C6 C11 C12 O 179.4(4) . . . . ?
C13 C11 C12 C15 177.6(3) . . . . ?
C6 C11 C12 C15 -1.4(4) . . . . ?
C12 C11 C13 C5 -177.4(4) . . . . ?
C6 C11 C13 C5 1.4(7) . . . . ?
C16 C5 C13 C11 177.1(4) . . . . ?
C3 C5 C13 C11 -0.5(6) . . . . ?
N C9 C14 C16 -179.5(4) . . . . ?
C7 C9 C14 C16 1.5(5) . . . . ?
C10 C4 C15 C18 -1.1(5) . . . . ?
C6 C4 C15 C18 178.3(3) . . . . ?
C10 C4 C15 C12 179.1(3) . . . . ?
C6 C4 C15 C12 -1.5(4) . . . . ?
O C12 C15 C4 -178.9(4) . . . . ?
C11 C12 C15 C4 1.8(4) . . . . ?
O C12 C15 C18 1.2(6) . . . . ?
C11 C12 C15 C18 -178.0(4) . . . . ?
C9 C14 C16 C5 -1.4(6) . . . . ?
C3 C5 C16 C14 0.0(5) . . . . ?
C13 C5 C16 C14 -177.8(4) . . . . ?
C10 C2 C17 C18 -1.2(6) . . . . ?
Br1 C2 C17 C18 179.6(3) . . . . ?
C2 C17 C18 C15 0.2(6) . . . . ?
C4 C15 C18 C17 0.9(5) . . . . ?
C12 C15 C18 C17 -179.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1854436'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 N O'
_chemical_formula_weight         387.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   11.8151(19)
_cell_length_b                   10.1351(12)
_cell_length_c                   16.826(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.561(13)
_cell_angle_gamma                90.00
_cell_volume                     1992.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1946
_cell_measurement_theta_min      3.4292
_cell_measurement_theta_max      29.2201

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7310
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3486
_reflns_number_gt                2439
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1014P)²+0.4897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3486
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_restrained_S_all      0.793
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.74833(13) 0.60041(14) 0.14282(10) 0.0488(4) Uani 1 1 d . . .
O1 O 1.32658(12) 1.03066(14) 0.02751(9) 0.0626(4) Uani 1 1 d . . .
C1 C 1.15162(16) 1.03620(17) 0.08613(10) 0.0440(5) Uani 1 1 d . . .
C2 C 1.02561(16) 0.83406(17) 0.09237(10) 0.0428(4) Uani 1 1 d . . .
C3 C 0.83955(16) 0.67662(17) 0.12607(11) 0.0420(4) Uani 1 1 d . . .
C4 C 1.01335(17) 0.70137(18) 0.06863(11) 0.0476(5) Uani 1 1 d . . .
H4 H 1.0681 0.6638 0.0412 0.057 Uiso 1 1 calc R . .
C5 C 1.25744(16) 1.09079(19) 0.06136(11) 0.0465(5) Uani 1 1 d . . .
C6 C 0.75265(15) 0.45907(17) 0.13905(11) 0.0442(5) Uani 1 1 d . . .
C7 C 0.92346(17) 0.62529(19) 0.08451(11) 0.0490(5) Uani 1 1 d . . .
H7 H 0.9183 0.5380 0.0673 0.059 Uiso 1 1 calc R . .
C8 C 1.12310(16) 0.90901(18) 0.07355(11) 0.0456(5) Uani 1 1 d . . .
H8 H 1.1745 0.8605 0.0485 0.055 Uiso 1 1 calc R . .
C9 C 0.85168(16) 0.80853(17) 0.15064(11) 0.0452(5) Uani 1 1 d . . .
H9 H 0.7979 0.8456 0.1791 0.054 Uiso 1 1 calc R . .
C10 C 1.16925(16) 1.26393(18) 0.12006(10) 0.0439(5) Uani 1 1 d . . .
C11 C 0.94115(16) 0.88399(18) 0.13364(11) 0.0458(5) Uani 1 1 d . . .
H11 H 0.9457 0.9716 0.1502 0.055 Uiso 1 1 calc R . .
C12 C 0.64706(16) 0.65687(17) 0.16537(11) 0.0429(4) Uani 1 1 d . . .
C13 C 0.60323(18) 0.60506(19) 0.23006(12) 0.0518(5) Uani 1 1 d . . .
H13 H 0.6410 0.5358 0.2590 0.062 Uiso 1 1 calc R . .
C14 C 1.26410(16) 1.23035(18) 0.08586(10) 0.0434(5) Uani 1 1 d . . .
C15 C 0.83002(17) 0.38901(19) 0.19191(12) 0.0520(5) Uani 1 1 d . . .
H15 H 0.8823 0.4335 0.2293 0.062 Uiso 1 1 calc R . .
C16 C 1.35070(18) 1.3213(2) 0.08013(12) 0.0545(5) Uani 1 1 d . . .
H16 H 1.4149 1.2978 0.0573 0.065 Uiso 1 1 calc R . .
C17 C 1.09192(18) 1.14625(19) 0.12343(13) 0.0478(5) Uani 1 1 d . . .
C18 C 0.6782(2) 0.2554(2) 0.08180(15) 0.0649(6) Uani 1 1 d . . .
H18 H 0.6268 0.2104 0.0440 0.078 Uiso 1 1 calc R . .
C19 C 0.59077(18) 0.75995(18) 0.12259(12) 0.0519(5) Uani 1 1 d . . .
H19 H 0.6192 0.7958 0.0786 0.062 Uiso 1 1 calc R . .
C20 C 1.2429(2) 1.4815(2) 0.14225(12) 0.0618(6) Uani 1 1 d . . .
H20 H 1.2359 1.5670 0.1610 0.074 Uiso 1 1 calc R . .
C21 C 0.67592(18) 0.39185(19) 0.08410(12) 0.0550(5) Uani 1 1 d . . .
H21 H 0.6225 0.4381 0.0485 0.066 Uiso 1 1 calc R . .
C22 C 0.7550(2) 0.1864(2) 0.13437(15) 0.0654(6) Uani 1 1 d . . .
H22 H 0.7559 0.0947 0.1326 0.078 Uiso 1 1 calc R . .
C23 C 1.15770(19) 1.3911(2) 0.14794(12) 0.0562(5) Uani 1 1 d . . .
H23 H 1.0932 1.4150 0.1702 0.067 Uiso 1 1 calc R . .
C24 C 0.49138(19) 0.8093(2) 0.14606(14) 0.0628(6) Uani 1 1 d . . .
H24 H 0.4534 0.8792 0.1179 0.075 Uiso 1 1 calc R . .
C25 C 0.4486(2) 0.7560(2) 0.21033(15) 0.0658(6) Uani 1 1 d . . .
H25 H 0.3814 0.7891 0.2253 0.079 Uiso 1 1 calc R . .
C26 C 0.8305(2) 0.25248(19) 0.18972(14) 0.0604(6) Uani 1 1 d . . .
H26 H 0.8825 0.2056 0.2260 0.072 Uiso 1 1 calc R . .
C27 C 1.3391(2) 1.4466(2) 0.10895(13) 0.0635(6) Uani 1 1 d . . .
H27 H 1.3964 1.5086 0.1061 0.076 Uiso 1 1 calc R . .
C28 C 0.5047(2) 0.6544(2) 0.25224(14) 0.0631(6) Uani 1 1 d . . .
H28 H 0.4760 0.6184 0.2960 0.076 Uiso 1 1 calc R . .
H32 H 1.0807(16) 1.1256(18) 0.1801(12) 0.054(5) Uiso 1 1 d . . .
H31 H 1.014(2) 1.162(2) 0.0937(12) 0.063(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.389(2) . ?
N1 C12 1.428(2) . ?
N1 C6 1.435(2) . ?
O1 C5 1.225(2) . ?
C1 C8 1.341(3) . ?
C1 C5 1.483(3) . ?
C1 C17 1.506(3) . ?
C2 C11 1.393(2) . ?
C2 C4 1.404(2) . ?
C2 C8 1.453(3) . ?
C3 C7 1.396(3) . ?
C3 C9 1.400(2) . ?
C4 C7 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C14 1.472(3) . ?
C6 C15 1.374(3) . ?
C6 C21 1.375(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.369(3) . ?
C9 H9 0.9300 . ?
C10 C14 1.377(3) . ?
C10 C23 1.385(3) . ?
C10 C17 1.509(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 C19 1.382(3) . ?
C13 C28 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C16 1.391(3) . ?
C15 C26 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C27 1.373(3) . ?
C16 H16 0.9300 . ?
C17 H32 1.00(2) . ?
C17 H31 1.00(2) . ?
C18 C22 1.362(3) . ?
C18 C21 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C23 1.375(3) . ?
C20 C27 1.386(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C26 1.366(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C28 1.364(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
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
C3 N1 C12 122.52(14) . . ?
C3 N1 C6 120.83(15) . . ?
C12 N1 C6 116.65(14) . . ?
C8 C1 C5 121.12(17) . . ?
C8 C1 C17 130.95(17) . . ?
C5 C1 C17 107.92(15) . . ?
C11 C2 C4 116.00(17) . . ?
C11 C2 C8 124.65(16) . . ?
C4 C2 C8 119.35(16) . . ?
N1 C3 C7 121.67(16) . . ?
N1 C3 C9 121.30(16) . . ?
C7 C3 C9 117.03(17) . . ?
C7 C4 C2 122.24(17) . . ?
C7 C4 H4 118.9 . . ?
C2 C4 H4 118.9 . . ?
O1 C5 C14 126.62(18) . . ?
O1 C5 C1 126.40(18) . . ?
C14 C5 C1 106.98(16) . . ?
C15 C6 C21 119.18(18) . . ?
C15 C6 N1 120.78(17) . . ?
C21 C6 N1 120.00(17) . . ?
C4 C7 C3 121.11(17) . . ?
C4 C7 H7 119.4 . . ?
C3 C7 H7 119.4 . . ?
C1 C8 C2 131.04(17) . . ?
C1 C8 H8 114.5 . . ?
C2 C8 H8 114.5 . . ?
C11 C9 C3 121.33(17) . . ?
C11 C9 H9 119.3 . . ?
C3 C9 H9 119.3 . . ?
C14 C10 C23 119.94(18) . . ?
C14 C10 C17 110.82(17) . . ?
C23 C10 C17 129.20(18) . . ?
C9 C11 C2 122.28(17) . . ?
C9 C11 H11 118.9 . . ?
C2 C11 H11 118.9 . . ?
C13 C12 C19 119.44(18) . . ?
C13 C12 N1 119.08(16) . . ?
C19 C12 N1 121.46(17) . . ?
C28 C13 C12 120.76(19) . . ?
C28 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C10 C14 C16 121.20(18) . . ?
C10 C14 C5 109.99(17) . . ?
C16 C14 C5 128.79(18) . . ?
C6 C15 C26 120.28(19) . . ?
C6 C15 H15 119.9 . . ?
C26 C15 H15 119.9 . . ?
C27 C16 C14 118.4(2) . . ?
C27 C16 H16 120.8 . . ?
C14 C16 H16 120.8 . . ?
C1 C17 C10 104.24(16) . . ?
C1 C17 H32 112.2(11) . . ?
C10 C17 H32 111.5(11) . . ?
C1 C17 H31 111.5(12) . . ?
C10 C17 H31 112.2(12) . . ?
H32 C17 H31 105.4(16) . . ?
C22 C18 C21 120.6(2) . . ?
C22 C18 H18 119.7 . . ?
C21 C18 H18 119.7 . . ?
C12 C19 C24 119.12(19) . . ?
C12 C19 H19 120.4 . . ?
C24 C19 H19 120.4 . . ?
C23 C20 C27 120.7(2) . . ?
C23 C20 H20 119.6 . . ?
C27 C20 H20 119.6 . . ?
C6 C21 C18 120.0(2) . . ?
C6 C21 H21 120.0 . . ?
C18 C21 H21 120.0 . . ?
C18 C22 C26 119.7(2) . . ?
C18 C22 H22 120.1 . . ?
C26 C22 H22 120.1 . . ?
C20 C23 C10 119.1(2) . . ?
C20 C23 H23 120.5 . . ?
C10 C23 H23 120.5 . . ?
C25 C24 C19 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C28 C25 C24 119.8(2) . . ?
C28 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C22 C26 C15 120.2(2) . . ?
C22 C26 H26 119.9 . . ?
C15 C26 H26 119.9 . . ?
C16 C27 C20 120.6(2) . . ?
C16 C27 H27 119.7 . . ?
C20 C27 H27 119.7 . . ?
C25 C28 C13 120.2(2) . . ?
C25 C28 H28 119.9 . . ?
C13 C28 H28 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1854437'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 Br N O'
_chemical_formula_weight         465.35

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c '

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

_cell_length_a                   20.0505(16)
_cell_length_b                   7.2077(8)
_cell_length_c                   15.0738(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.374(9)
_cell_angle_gamma                90.00
_cell_volume                     2176.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1204
_cell_measurement_theta_min      2.9231
_cell_measurement_theta_max      29.4659

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_T_max  0.5466
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9245
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3825
_reflns_number_gt                2087
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.23436(2) 0.75027(8) -0.04583(4) 0.0795(2) Uani 1 1 d . . .
C1 C 0.83931(19) 0.7652(6) 0.2221(2) 0.0442(10) Uani 1 1 d . . .
N N 0.67128(16) 0.9909(5) 0.3461(2) 0.0493(9) Uani 1 1 d . . .
C3 C 1.04384(19) 0.9183(6) 0.1011(2) 0.0440(10) Uani 1 1 d . . .
O O 0.99935(14) 0.4477(4) 0.11058(19) 0.0631(8) Uani 1 1 d . . .
C5 C 0.7319(2) 0.7265(7) 0.2888(3) 0.0496(11) Uani 1 1 d . . .
C6 C 0.95225(19) 0.7441(6) 0.1513(2) 0.0432(10) Uani 1 1 d . . .
C7 C 0.8337(2) 0.9532(6) 0.2391(3) 0.0518(11) Uani 1 1 d . . .
C8 C 1.05640(19) 0.7355(6) 0.0818(2) 0.0432(10) Uani 1 1 d . . .
C9 C 0.7797(2) 1.0277(7) 0.2800(3) 0.0501(11) Uani 1 1 d . . .
C10 C 0.5508(3) 0.7828(7) 0.4987(4) 0.0644(14) Uani 1 1 d . . .
C11 C 0.9787(2) 0.9398(6) 0.1470(3) 0.0494(11) Uani 1 1 d . . .
C12 C 1.1566(2) 0.8159(7) 0.0154(3) 0.0534(12) Uani 1 1 d . . .
C13 C 1.1134(2) 0.6808(7) 0.0384(3) 0.0479(11) Uani 1 1 d . . .
C14 C 1.0886(2) 1.0538(7) 0.0773(3) 0.0552(12) Uani 1 1 d . . .
C15 C 0.72751(19) 0.9147(6) 0.3049(2) 0.0434(10) Uani 1 1 d . . .
C16 C 0.8958(2) 0.6757(7) 0.1813(3) 0.0480(11) Uani 1 1 d . . .
C17 C 0.63964(18) 1.1526(6) 0.3120(3) 0.0430(10) Uani 1 1 d . . .
C18 C 0.6098(2) 1.2761(6) 0.3679(3) 0.0497(11) Uani 1 1 d . . .
C19 C 0.6861(2) 0.8144(6) 0.4831(3) 0.0528(12) Uani 1 1 d . . .
C20 C 0.6441(2) 0.8946(5) 0.4186(3) 0.0429(10) Uani 1 1 d . . .
C21 C 1.0025(2) 0.6172(6) 0.1128(3) 0.0457(10) Uani 1 1 d . . .
C22 C 0.7861(2) 0.6541(7) 0.2484(3) 0.0502(11) Uani 1 1 d . . .
C23 C 0.5762(2) 0.8784(6) 0.4276(3) 0.0552(12) Uani 1 1 d . . .
C24 C 0.6367(2) 1.1895(7) 0.2215(3) 0.0551(12) Uani 1 1 d . . .
C26 C 0.6037(3) 1.3443(7) 0.1887(4) 0.0636(13) Uani 1 1 d . . .
C27 C 0.5923(3) 0.7039(7) 0.5616(3) 0.0659(14) Uani 1 1 d . . .
C28 C 0.5752(2) 1.4282(6) 0.3330(4) 0.0600(13) Uani 1 1 d . . .
C29 C 0.6605(3) 0.7190(7) 0.5534(3) 0.0659(14) Uani 1 1 d . . .
C30 C 1.1452(2) 0.9996(8) 0.0341(3) 0.0588(13) Uani 1 1 d . . .
C31 C 0.5721(2) 1.4615(7) 0.2441(4) 0.0671(15) Uani 1 1 d . . .
H6 H 0.8857(15) 0.547(5) 0.1712(19) 0.028(9) Uiso 1 1 d . . .
H13 H 0.5550(17) 1.502(5) 0.373(2) 0.036(10) Uiso 1 1 d . . .
H3 H 1.0813(16) 1.177(5) 0.088(2) 0.031(10) Uiso 1 1 d . . .
H12 H 0.613(2) 1.251(6) 0.429(3) 0.071(14) Uiso 1 1 d . . .
H4 H 0.987(2) 0.989(5) 0.201(3) 0.061(14) Uiso 1 1 d . . .
H7 H 0.7871(18) 0.522(5) 0.234(2) 0.051(11) Uiso 1 1 d . . .
H19 H 0.7318(17) 0.828(5) 0.482(2) 0.032(10) Uiso 1 1 d . . .
H5 H 0.9479(17) 1.024(5) 0.116(2) 0.037(10) Uiso 1 1 d . . .
H11 H 0.6577(15) 1.107(4) 0.1847(19) 0.021(9) Uiso 1 1 d . . .
H15 H 0.546(2) 0.926(6) 0.385(3) 0.070(14) Uiso 1 1 d . . .
H1 H 1.1173(17) 0.554(5) 0.026(2) 0.036(10) Uiso 1 1 d . . .
H2 H 1.172(2) 1.082(6) 0.017(3) 0.063(15) Uiso 1 1 d . . .
H10 H 0.7785(18) 1.149(6) 0.292(2) 0.051(12) Uiso 1 1 d . . .
H9 H 0.8655(19) 1.041(5) 0.225(2) 0.056(13) Uiso 1 1 d . . .
H8 H 0.6988(18) 0.653(5) 0.304(2) 0.044(12) Uiso 1 1 d . . .
H18 H 0.691(2) 0.666(6) 0.601(3) 0.076(14) Uiso 1 1 d . . .
H14 H 0.550(2) 1.568(6) 0.225(3) 0.080(15) Uiso 1 1 d . . .
H17 H 0.572(2) 0.631(6) 0.612(3) 0.088(16) Uiso 1 1 d . . .
H16 H 0.505(3) 0.780(6) 0.502(3) 0.096(18) Uiso 1 1 d . . .
H20 H 0.608(2) 1.377(6) 0.125(3) 0.083(15) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.903(4) . ?
C1 C7 1.385(6) . ?
C1 C22 1.404(6) . ?
C1 C16 1.461(6) . ?
N C17 1.414(4) . ?
N C15 1.420(5) . ?
N C20 1.422(5) . ?
C3 C8 1.375(5) . ?
C3 C14 1.384(6) . ?
C3 C11 1.511(6) . ?
O C21 1.223(5) . ?
C5 C22 1.372(6) . ?
C5 C15 1.381(6) . ?
C5 H8 0.89(4) . ?
C6 C16 1.331(6) . ?
C6 C21 1.495(5) . ?
C6 C11 1.509(6) . ?
C7 C9 1.377(6) . ?
C7 H9 0.93(4) . ?
C8 C13 1.396(6) . ?
C8 C21 1.469(5) . ?
C9 C15 1.390(6) . ?
C9 H10 0.90(4) . ?
C10 C27 1.361(7) . ?
C10 C23 1.389(6) . ?
C10 H16 0.92(5) . ?
C11 H4 0.90(4) . ?
C11 H5 0.97(3) . ?
C12 C13 1.359(6) . ?
C12 C30 1.375(6) . ?
C13 H1 0.94(3) . ?
C14 C30 1.389(6) . ?
C14 H3 0.92(3) . ?
C16 H6 0.96(3) . ?
C17 C18 1.379(6) . ?
C17 C24 1.388(6) . ?
C18 C28 1.389(6) . ?
C18 H12 0.94(4) . ?
C19 C29 1.380(6) . ?
C19 C20 1.386(5) . ?
C19 H19 0.92(3) . ?
C20 C23 1.379(6) . ?
C22 H7 0.97(4) . ?
C23 H15 0.93(4) . ?
C24 C26 1.380(6) . ?
C24 H11 0.93(3) . ?
C26 C31 1.362(7) . ?
C26 H20 0.99(4) . ?
C27 C29 1.381(7) . ?
C27 H17 1.02(5) . ?
C28 C31 1.360(7) . ?
C28 H13 0.91(3) . ?
C29 H18 0.99(4) . ?
C30 H2 0.85(4) . ?
C31 H14 0.93(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C22 116.0(4) . . ?
C7 C1 C16 125.5(4) . . ?
C22 C1 C16 118.6(4) . . ?
C17 N C15 120.8(3) . . ?
C17 N C20 120.1(3) . . ?
C15 N C20 118.9(3) . . ?
C8 C3 C14 119.7(4) . . ?
C8 C3 C11 111.4(4) . . ?
C14 C3 C11 128.9(4) . . ?
C22 C5 C15 120.6(4) . . ?
C22 C5 H8 120(2) . . ?
C15 C5 H8 119(2) . . ?
C16 C6 C21 120.1(4) . . ?
C16 C6 C11 131.8(4) . . ?
C21 C6 C11 108.2(4) . . ?
C9 C7 C1 122.4(5) . . ?
C9 C7 H9 113(2) . . ?
C1 C7 H9 124(2) . . ?
C3 C8 C13 122.0(4) . . ?
C3 C8 C21 110.2(4) . . ?
C13 C8 C21 127.8(4) . . ?
C7 C9 C15 120.5(5) . . ?
C7 C9 H10 120(3) . . ?
C15 C9 H10 119(3) . . ?
C27 C10 C23 120.8(5) . . ?
C27 C10 H16 123(3) . . ?
C23 C10 H16 117(3) . . ?
C6 C11 C3 103.6(3) . . ?
C6 C11 H4 113(3) . . ?
C3 C11 H4 108(3) . . ?
C6 C11 H5 112.8(19) . . ?
C3 C11 H5 113(2) . . ?
H4 C11 H5 107(3) . . ?
C13 C12 C30 121.6(4) . . ?
C13 C12 Br1 119.3(4) . . ?
C30 C12 Br1 119.0(4) . . ?
C12 C13 C8 117.4(4) . . ?
C12 C13 H1 126(2) . . ?
C8 C13 H1 116(2) . . ?
C3 C14 C30 118.3(5) . . ?
C3 C14 H3 122(2) . . ?
C30 C14 H3 120(2) . . ?
C5 C15 C9 118.3(4) . . ?
C5 C15 N 120.9(4) . . ?
C9 C15 N 120.8(4) . . ?
C6 C16 C1 131.6(4) . . ?
C6 C16 H6 119(2) . . ?
C1 C16 H6 109(2) . . ?
C18 C17 C24 118.4(4) . . ?
C18 C17 N 120.6(4) . . ?
C24 C17 N 121.0(4) . . ?
C17 C18 C28 120.0(4) . . ?
C17 C18 H12 118(3) . . ?
C28 C18 H12 122(3) . . ?
C29 C19 C20 120.8(5) . . ?
C29 C19 H19 118(2) . . ?
C20 C19 H19 121(2) . . ?
C23 C20 C19 118.0(4) . . ?
C23 C20 N 121.9(4) . . ?
C19 C20 N 120.1(4) . . ?
O C21 C8 127.5(4) . . ?
O C21 C6 125.9(4) . . ?
C8 C21 C6 106.5(4) . . ?
C5 C22 C1 122.3(4) . . ?
C5 C22 H7 119(2) . . ?
C1 C22 H7 118(2) . . ?
C20 C23 C10 120.9(5) . . ?
C20 C23 H15 121(3) . . ?
C10 C23 H15 118(3) . . ?
C26 C24 C17 120.5(5) . . ?
C26 C24 H11 121.8(18) . . ?
C17 C24 H11 117.7(18) . . ?
C31 C26 C24 120.6(5) . . ?
C31 C26 H20 120(3) . . ?
C24 C26 H20 119(3) . . ?
C10 C27 C29 119.0(5) . . ?
C10 C27 H17 119(2) . . ?
C29 C27 H17 122(2) . . ?
C31 C28 C18 121.0(5) . . ?
C31 C28 H13 123(2) . . ?
C18 C28 H13 116(2) . . ?
C19 C29 C27 120.6(5) . . ?
C19 C29 H18 120(3) . . ?
C27 C29 H18 119(3) . . ?
C12 C30 C14 120.9(5) . . ?
C12 C30 H2 119(3) . . ?
C14 C30 H2 120(3) . . ?
C28 C31 C26 119.4(5) . . ?
C28 C31 H14 117(3) . . ?
C26 C31 H14 123(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
C22 C1 C7 C9 0.5(6) . . . . ?
C16 C1 C7 C9 -178.2(4) . . . . ?
C14 C3 C8 C13 0.0(6) . . . . ?
C11 C3 C8 C13 179.2(4) . . . . ?
C14 C3 C8 C21 -179.8(3) . . . . ?
C11 C3 C8 C21 -0.6(5) . . . . ?
C1 C7 C9 C15 -0.9(7) . . . . ?
C16 C6 C11 C3 -177.3(4) . . . . ?
C21 C6 C11 C3 2.4(4) . . . . ?
C8 C3 C11 C6 -1.1(5) . . . . ?
C14 C3 C11 C6 178.0(4) . . . . ?
C30 C12 C13 C8 0.2(6) . . . . ?
Br1 C12 C13 C8 -178.9(3) . . . . ?
C3 C8 C13 C12 -0.1(6) . . . . ?
C21 C8 C13 C12 179.6(4) . . . . ?
C8 C3 C14 C30 0.1(6) . . . . ?
C11 C3 C14 C30 -179.0(4) . . . . ?
C22 C5 C15 C9 -0.6(6) . . . . ?
C22 C5 C15 N 179.5(4) . . . . ?
C7 C9 C15 C5 0.9(6) . . . . ?
C7 C9 C15 N -179.2(4) . . . . ?
C17 N C15 C5 -134.1(4) . . . . ?
C20 N C15 C5 41.4(5) . . . . ?
C17 N C15 C9 46.0(5) . . . . ?
C20 N C15 C9 -138.5(4) . . . . ?
C21 C6 C16 C1 179.5(4) . . . . ?
C11 C6 C16 C1 -0.9(8) . . . . ?
C7 C1 C16 C6 -0.6(7) . . . . ?
C22 C1 C16 C6 -179.3(4) . . . . ?
C15 N C17 C18 -148.2(4) . . . . ?
C20 N C17 C18 36.4(5) . . . . ?
C15 N C17 C24 33.0(6) . . . . ?
C20 N C17 C24 -142.5(4) . . . . ?
C24 C17 C18 C28 3.0(6) . . . . ?
N C17 C18 C28 -175.9(4) . . . . ?
C29 C19 C20 C23 0.9(6) . . . . ?
C29 C19 C20 N -179.4(4) . . . . ?
C17 N C20 C23 36.6(5) . . . . ?
C15 N C20 C23 -138.9(4) . . . . ?
C17 N C20 C19 -143.0(4) . . . . ?
C15 N C20 C19 41.4(5) . . . . ?
C3 C8 C21 O -175.8(4) . . . . ?
C13 C8 C21 O 4.4(7) . . . . ?
C3 C8 C21 C6 2.1(4) . . . . ?
C13 C8 C21 C6 -177.7(3) . . . . ?
C16 C6 C21 O -5.1(6) . . . . ?
C11 C6 C21 O 175.2(4) . . . . ?
C16 C6 C21 C8 177.0(3) . . . . ?
C11 C6 C21 C8 -2.7(4) . . . . ?
C15 C5 C22 C1 0.3(7) . . . . ?
C7 C1 C22 C5 -0.2(6) . . . . ?
C16 C1 C22 C5 178.6(4) . . . . ?
C19 C20 C23 C10 -0.7(6) . . . . ?
N C20 C23 C10 179.7(4) . . . . ?
C27 C10 C23 C20 0.5(7) . . . . ?
C18 C17 C24 C26 -1.2(6) . . . . ?
N C17 C24 C26 177.7(4) . . . . ?
C17 C24 C26 C31 -1.4(7) . . . . ?
C23 C10 C27 C29 -0.5(7) . . . . ?
C17 C18 C28 C31 -2.3(7) . . . . ?
C20 C19 C29 C27 -0.9(7) . . . . ?
C10 C27 C29 C19 0.7(7) . . . . ?
C13 C12 C30 C14 -0.2(7) . . . . ?
Br1 C12 C30 C14 178.9(3) . . . . ?
C3 C14 C30 C12 0.0(7) . . . . ?
C18 C28 C31 C26 -0.3(7) . . . . ?
C24 C26 C31 C28 2.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.074
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1854440'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 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         ?
_chemical_formula_sum            'C31 H25 Cl6 N O'
_chemical_formula_weight         640.22

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                   10.3529(6)
_cell_length_b                   10.8037(7)
_cell_length_c                   14.0088(8)
_cell_angle_alpha                85.865(5)
_cell_angle_beta                 87.637(5)
_cell_angle_gamma                83.127(5)
_cell_volume                     1550.73(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2074
_cell_measurement_theta_min      2.911
_cell_measurement_theta_max      29.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.579
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9582
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5447
_reflns_number_gt                3168
_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)+(0.1433P)²+0.1877P] 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         5447
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_ref         0.2689
_refine_ls_wR_factor_gt          0.2322
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.2419(4) 0.3867(4) 1.0992(3) 0.0485(9) Uani 1 1 d . . . . .
C2 C 0.1315(3) 0.4783(3) 1.1294(3) 0.0483(9) Uani 1 1 d . . . . .
C3 C 0.0543(4) 0.4763(4) 1.2130(3) 0.0600(10) Uani 1 1 d . . . . .
H3 H 0.0661 0.4097 1.2589 0.072 Uiso 1 1 calc R U . . .
C4 C -0.0402(4) 0.5755(4) 1.2261(3) 0.0644(11) Uani 1 1 d . . . . .
H4 H -0.0919 0.5757 1.2820 0.077 Uiso 1 1 calc R U . . .
C5 C -0.0601(4) 0.6760(4) 1.1574(3) 0.0619(11) Uani 1 1 d . . . . .
C6 C 0.0185(4) 0.6761(4) 1.0741(3) 0.0585(10) Uani 1 1 d . . . . .
H6 H 0.0064 0.7421 1.0277 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1156(3) 0.5770(3) 1.0606(3) 0.0474(9) Uani 1 1 d . . . . .
C8 C 0.2108(4) 0.5584(3) 0.9782(3) 0.0504(9) Uani 1 1 d . . . . .
H8A H 0.2643 0.6264 0.9698 0.060 Uiso 1 1 calc R U . . .
H8B H 0.1663 0.5529 0.9194 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2918(3) 0.4372(3) 1.0057(2) 0.0466(9) Uani 1 1 d . . . . .
C10 C 0.3962(3) 0.3763(3) 0.9606(3) 0.0479(9) Uani 1 1 d . . . . .
H10 H 0.4302 0.3022 0.9931 0.057 Uiso 1 1 calc R U . . .
C11 C 0.4648(3) 0.4058(3) 0.8709(2) 0.0465(9) Uani 1 1 d . . . . .
C12 C 0.5789(4) 0.3284(3) 0.8466(3) 0.0499(9) Uani 1 1 d . . . . .
H12 H 0.6067 0.2601 0.8879 0.060 Uiso 1 1 calc R U . . .
C13 C 0.6507(4) 0.3510(4) 0.7633(3) 0.0538(10) Uani 1 1 d . . . . .
H13 H 0.7260 0.2983 0.7499 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6114(4) 0.4522(3) 0.6989(3) 0.0477(9) Uani 1 1 d . . . . .
C15 C 0.4970(4) 0.5293(3) 0.7225(3) 0.0496(9) Uani 1 1 d . . . . .
H15 H 0.4683 0.5969 0.6807 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4271(4) 0.5068(3) 0.8056(3) 0.0496(9) Uani 1 1 d . . . . .
H16 H 0.3523 0.5602 0.8192 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7605(4) 0.3724(4) 0.5693(3) 0.0546(10) Uani 1 1 d . . . . .
C18 C 0.7059(5) 0.2710(4) 0.5454(3) 0.0741(13) Uani 1 1 d . . . . .
H18 H 0.6183 0.2644 0.5594 0.089 Uiso 1 1 calc R U . . .
C19 C 0.7833(7) 0.1772(5) 0.4995(4) 0.103(2) Uani 1 1 d . . . . .
H19 H 0.7477 0.1064 0.4840 0.123 Uiso 1 1 calc R U . . .
C20 C 0.9108(8) 0.1884(6) 0.4771(4) 0.111(2) Uani 1 1 d . . . . .
H20 H 0.9610 0.1268 0.4444 0.133 Uiso 1 1 calc R U . . .
C21 C 0.9648(6) 0.2890(7) 0.5022(5) 0.107(2) Uani 1 1 d . . . . .
H21 H 1.0522 0.2962 0.4879 0.128 Uiso 1 1 calc R U . . .
C22 C 0.8895(4) 0.3795(5) 0.5487(3) 0.0760(13) Uani 1 1 d . . . . .
H22 H 0.9270 0.4478 0.5668 0.091 Uiso 1 1 calc R U . . .
C23 C 0.6745(4) 0.5935(4) 0.5638(3) 0.0523(10) Uani 1 1 d . . . . .
C24 C 0.6637(4) 0.6038(4) 0.4648(3) 0.0659(11) Uani 1 1 d . . . . .
H24 H 0.6621 0.5321 0.4322 0.079 Uiso 1 1 calc R U . . .
C25 C 0.6554(5) 0.7188(5) 0.4144(3) 0.0834(15) Uani 1 1 d . . . . .
H25 H 0.6471 0.7245 0.3483 0.100 Uiso 1 1 calc R U . . .
C26 C 0.6594(5) 0.8243(5) 0.4619(4) 0.0826(14) Uani 1 1 d . . . . .
H26 H 0.6537 0.9019 0.4279 0.099 Uiso 1 1 calc R U . . .
C27 C 0.6717(5) 0.8167(4) 0.5584(4) 0.0775(13) Uani 1 1 d . . . . .
H27 H 0.6744 0.8891 0.5900 0.093 Uiso 1 1 calc R U . . .
C28 C 0.6804(4) 0.7012(4) 0.6106(3) 0.0603(11) Uani 1 1 d . . . . .
H28 H 0.6902 0.6965 0.6765 0.072 Uiso 1 1 calc R U . . .
C29 C -0.1648(5) 0.7837(5) 1.1734(4) 0.0843(15) Uani 1 1 d . . . . .
H29A H -0.1578 0.8486 1.1235 0.126 Uiso 1 1 calc R U . . .
H29B H -0.1541 0.8158 1.2343 0.126 Uiso 1 1 calc R U . . .
H29C H -0.2490 0.7549 1.1723 0.126 Uiso 1 1 calc R U . . .
C30 C 0.1090(5) 0.0683(5) 0.1910(4) 0.0815(14) Uani 1 1 d . . . . .
H30 H 0.1748 0.1253 0.1964 0.098 Uiso 1 1 calc R U . . .
C31 C 0.5376(5) 0.1050(6) 0.1882(4) 0.1029(19) Uani 1 1 d . . . . .
H31 H 0.4672 0.1738 0.1802 0.123 Uiso 1 1 calc R U . . .
Cl1 Cl 0.11569(18) -0.03713(16) 0.29052(12) 0.1168(6) Uani 1 1 d . . . . .
Cl2 Cl 0.64115(16) 0.13954(16) 0.27804(15) 0.1183(6) Uani 1 1 d . . . . .
Cl3 Cl -0.04119(18) 0.1545(2) 0.18474(16) 0.1408(8) Uani 1 1 d . . . . .
Cl6 Cl 0.6253(3) 0.0916(3) 0.08089(14) 0.1808(12) Uani 1 1 d . . . . .
Cl9 Cl 0.1447(2) -0.0125(2) 0.08720(13) 0.1407(8) Uani 1 1 d . . . . .
Cl14 Cl 0.47104(19) -0.02985(17) 0.22706(17) 0.1345(7) Uani 1 1 d . . . . .
N1 N 0.6842(3) 0.4747(3) 0.6142(2) 0.0556(8) Uani 1 1 d . . . . .
O1 O 0.2828(3) 0.2890(3) 1.1437(2) 0.0641(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.225(5) . ?
C1 C9 1.479(5) . ?
C1 C2 1.488(5) . ?
C2 C7 1.385(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(6) . ?
C5 C29 1.515(6) . ?
C6 C7 1.396(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.495(5) . ?
C8 C9 1.502(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.354(5) . ?
C10 C11 1.453(5) . ?
C10 H10 0.9300 . ?
C11 C16 1.401(5) . ?
C11 C12 1.408(5) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(5) . ?
C13 H13 0.9300 . ?
C14 N1 1.401(4) . ?
C14 C15 1.405(5) . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.359(6) . ?
C17 C22 1.365(6) . ?
C17 N1 1.447(5) . ?
C18 C19 1.393(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.361(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.385(5) . ?
C23 C24 1.390(6) . ?
C23 N1 1.415(5) . ?
C24 C25 1.380(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 Cl3 1.716(5) . ?
C30 Cl1 1.734(6) . ?
C30 Cl9 1.753(5) . ?
C30 H30 0.9800 . ?
C31 Cl14 1.729(7) . ?
C31 Cl6 1.730(6) . ?
C31 Cl2 1.774(7) . ?
C31 H31 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C9 127.2(3) . . ?
O1 C1 C2 126.3(3) . . ?
C9 C1 C2 106.5(3) . . ?
C7 C2 C3 121.5(3) . . ?
C7 C2 C1 109.2(3) . . ?
C3 C2 C1 129.3(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 C29 120.3(4) . . ?
C4 C5 C29 120.6(4) . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 119.6(3) . . ?
C2 C7 C8 111.5(3) . . ?
C6 C7 C8 128.9(3) . . ?
C7 C8 C9 104.2(3) . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C1 120.7(4) . . ?
C10 C9 C8 130.7(3) . . ?
C1 C9 C8 108.6(3) . . ?
C9 C10 C11 131.7(4) . . ?
C9 C10 H10 114.2 . . ?
C11 C10 H10 114.2 . . ?
C16 C11 C12 116.5(3) . . ?
C16 C11 C10 125.2(3) . . ?
C12 C11 C10 118.3(3) . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 N1 120.6(3) . . ?
C13 C14 C15 117.5(3) . . ?
N1 C14 C15 121.9(3) . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 121.9(3) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C18 C17 C22 119.5(4) . . ?
C18 C17 N1 121.5(4) . . ?
C22 C17 N1 119.0(4) . . ?
C17 C18 C19 118.9(5) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.2(6) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C17 121.7(5) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C28 C23 C24 118.5(4) . . ?
C28 C23 N1 121.2(3) . . ?
C24 C23 N1 120.2(4) . . ?
C25 C24 C23 120.9(4) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 119.8(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C23 C28 C27 119.7(4) . . ?
C23 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C5 C29 H29A 109.5 . . ?
C5 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C5 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl3 C30 Cl1 110.9(3) . . ?
Cl3 C30 Cl9 110.6(3) . . ?
Cl1 C30 Cl9 109.5(3) . . ?
Cl3 C30 H30 108.6 . . ?
Cl1 C30 H30 108.6 . . ?
Cl9 C30 H30 108.6 . . ?
Cl14 C31 Cl6 112.9(4) . . ?
Cl14 C31 Cl2 107.9(3) . . ?
Cl6 C31 Cl2 109.5(3) . . ?
Cl14 C31 H31 108.8 . . ?
Cl6 C31 H31 108.8 . . ?
Cl2 C31 H31 108.8 . . ?
C14 N1 C23 121.9(3) . . ?
C14 N1 C17 120.3(3) . . ?
C23 N1 C17 117.4(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
O1 C1 C2 C7 179.6(4) . . . . ?
C9 C1 C2 C7 -0.4(4) . . . . ?
O1 C1 C2 C3 1.9(7) . . . . ?
C9 C1 C2 C3 -178.0(4) . . . . ?
C7 C2 C3 C4 0.2(6) . . . . ?
C1 C2 C3 C4 177.7(4) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C3 C4 C5 C29 179.8(4) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C29 C5 C6 C7 179.4(4) . . . . ?
C3 C2 C7 C6 -1.0(6) . . . . ?
C1 C2 C7 C6 -178.9(3) . . . . ?
C3 C2 C7 C8 179.3(3) . . . . ?
C1 C2 C7 C8 1.4(4) . . . . ?
C5 C6 C7 C2 1.0(6) . . . . ?
C5 C6 C7 C8 -179.4(4) . . . . ?
C2 C7 C8 C9 -1.8(4) . . . . ?
C6 C7 C8 C9 178.6(4) . . . . ?
O1 C1 C9 C10 -2.1(6) . . . . ?
C2 C1 C9 C10 177.8(3) . . . . ?
O1 C1 C9 C8 179.3(4) . . . . ?
C2 C1 C9 C8 -0.8(4) . . . . ?
C7 C8 C9 C10 -176.9(4) . . . . ?
C7 C8 C9 C1 1.5(4) . . . . ?
C1 C9 C10 C11 -178.9(3) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C9 C10 C11 C16 -5.0(6) . . . . ?
C9 C10 C11 C12 174.5(4) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
C10 C11 C12 C13 -179.1(3) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 N1 -179.8(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
N1 C14 C15 C16 -179.6(3) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C10 C11 C16 C15 179.6(3) . . . . ?
C22 C17 C18 C19 -0.6(7) . . . . ?
N1 C17 C18 C19 178.0(4) . . . . ?
C17 C18 C19 C20 -1.5(8) . . . . ?
C18 C19 C20 C21 2.3(10) . . . . ?
C19 C20 C21 C22 -1.1(10) . . . . ?
C20 C21 C22 C17 -1.0(9) . . . . ?
C18 C17 C22 C21 1.9(8) . . . . ?
N1 C17 C22 C21 -176.7(5) . . . . ?
C28 C23 C24 C25 -1.8(6) . . . . ?
N1 C23 C24 C25 -179.4(4) . . . . ?
C23 C24 C25 C26 0.8(7) . . . . ?
C24 C25 C26 C27 0.1(8) . . . . ?
C25 C26 C27 C28 0.0(8) . . . . ?
C24 C23 C28 C27 1.8(6) . . . . ?
N1 C23 C28 C27 179.4(4) . . . . ?
C26 C27 C28 C23 -1.0(7) . . . . ?
C13 C14 N1 C23 -159.0(4) . . . . ?
C15 C14 N1 C23 21.0(5) . . . . ?
C13 C14 N1 C17 28.5(5) . . . . ?
C15 C14 N1 C17 -151.4(4) . . . . ?
C28 C23 N1 C14 47.9(5) . . . . ?
C24 C23 N1 C14 -134.6(4) . . . . ?
C28 C23 N1 C17 -139.5(4) . . . . ?
C24 C23 N1 C17 38.0(5) . . . . ?
C18 C17 N1 C14 54.9(5) . . . . ?
C22 C17 N1 C14 -126.6(4) . . . . ?
C18 C17 N1 C23 -117.9(4) . . . . ?
C22 C17 N1 C23 60.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C28 H28 O1 0.93 2.56 3.489(5) 173.4 2_667
C31 H31 O1 0.98 2.21 3.163(6) 164.2 1_554
C30 H30 O1 0.98 2.27 3.172(6) 153.1 1_554

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1854442'
loop_
_audit_author_name
_audit_author_address
'XIAO CHENG'
;Zhejiang University
China
;
_audit_update_record             
;
2018-07-08 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 Br N O'
_chemical_formula_sum            'C28 H20 Br N O'
_chemical_formula_weight         466.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H n o br'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0904(8)
_cell_length_b                   10.0507(9)
_cell_length_c                   13.7049(11)
_cell_angle_alpha                87.174(7)
_cell_angle_beta                 71.568(7)
_cell_angle_gamma                81.559(7)
_cell_volume                     1175.04(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3299
_cell_measurement_theta_min      3.1273
_shelx_estimated_absorpt_T_max   0.553
_shelx_estimated_absorpt_T_min   0.478
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7257
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.134
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   42.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   83.0000  -57.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00   20.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  120.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0423402000
_diffrn_orient_matrix_UB_12      0.0369064000
_diffrn_orient_matrix_UB_13      0.0220115000
_diffrn_orient_matrix_UB_21      0.0682463000
_diffrn_orient_matrix_UB_22      -0.0167387000
_diffrn_orient_matrix_UB_23      -0.0425140000
_diffrn_orient_matrix_UB_31      -0.0211300000
_diffrn_orient_matrix_UB_32      0.0587191000
_diffrn_orient_matrix_UB_33      -0.0261573000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3009
_reflns_number_total             4273
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.2011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.87877(4) 0.92712(4) 0.40462(3) 0.07197(17) Uani 1 1 d . . . . .
O1 O 0.2177(3) 0.7715(2) 0.42430(17) 0.0668(7) Uani 1 1 d . . . . .
N1 N 0.4763(2) 0.3196(2) 0.90498(17) 0.0428(6) Uani 1 1 d . . . . .
C1 C 0.7021(4) 0.9404(3) 0.3598(2) 0.0515(8) Uani 1 1 d . . . . .
C2 C 0.6915(5) 1.0224(4) 0.2765(3) 0.0660(10) Uani 1 1 d . . . . .
H2 H 0.772941 1.070683 0.242497 0.079 Uiso 1 1 calc R . . . .
C3 C 0.5613(5) 1.0324(4) 0.2443(3) 0.0695(11) Uani 1 1 d . . . . .
H3 H 0.555892 1.088528 0.189110 0.083 Uiso 1 1 calc R . . . .
C4 C 0.4386(4) 0.9613(3) 0.2918(2) 0.0586(9) Uani 1 1 d . . . . .
H4 H 0.350821 0.968553 0.269865 0.070 Uiso 1 1 calc R . . . .
C5 C 0.4517(4) 0.8782(3) 0.3740(2) 0.0465(8) Uani 1 1 d . . . . .
C6 C 0.5802(3) 0.8676(3) 0.4084(2) 0.0425(7) Uani 1 1 d . . . . .
C7 C 0.5651(3) 0.7728(3) 0.4987(2) 0.0438(7) Uani 1 1 d . . . . .
H7A H 0.564835 0.819156 0.559189 0.053 Uiso 1 1 calc R . . . .
H7B H 0.649769 0.698371 0.483193 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4096(3) 0.7245(3) 0.5145(2) 0.0417(7) Uani 1 1 d . . . . .
C9 C 0.3397(4) 0.7892(3) 0.4360(2) 0.0480(8) Uani 1 1 d . . . . .
C10 C 0.3344(3) 0.6373(3) 0.5829(2) 0.0446(7) Uani 1 1 d . . . . .
H10 H 0.238685 0.623899 0.576703 0.054 Uiso 1 1 calc R . . . .
C11 C 0.3766(3) 0.5604(3) 0.6647(2) 0.0387(7) Uani 1 1 d . . . . .
C12 C 0.5066(3) 0.5719(3) 0.6950(2) 0.0418(7) Uani 1 1 d . . . . .
H12 H 0.572286 0.634104 0.661739 0.050 Uiso 1 1 calc R . . . .
C13 C 0.5413(3) 0.4938(3) 0.7729(2) 0.0392(7) Uani 1 1 d . . . . .
H13 H 0.629190 0.504325 0.791135 0.047 Uiso 1 1 calc R . . . .
C14 C 0.4453(3) 0.3993(3) 0.8243(2) 0.0370(7) Uani 1 1 d . . . . .
C15 C 0.3156(3) 0.3860(3) 0.7952(2) 0.0434(7) Uani 1 1 d . . . . .
H15 H 0.250529 0.323297 0.828410 0.052 Uiso 1 1 calc R . . . .
C16 C 0.2818(3) 0.4645(3) 0.7177(2) 0.0425(7) Uani 1 1 d . . . . .
H16 H 0.193604 0.453837 0.699952 0.051 Uiso 1 1 calc R . . . .
C17 C 0.6265(3) 0.2927(3) 0.9173(2) 0.0367(7) Uani 1 1 d . . . . .
C18 C 0.7628(3) 0.2704(3) 0.8335(2) 0.0425(7) Uani 1 1 d . . . . .
H18 H 0.756538 0.272150 0.766970 0.051 Uiso 1 1 calc R . . . .
C19 C 0.9072(3) 0.2456(3) 0.8494(2) 0.0507(8) Uani 1 1 d . . . . .
H19 H 0.997671 0.232977 0.793154 0.061 Uiso 1 1 calc R . . . .
C20 C 0.9193(4) 0.2394(3) 0.9473(3) 0.0582(9) Uani 1 1 d . . . . .
H20 H 1.016944 0.221392 0.957195 0.070 Uiso 1 1 calc R . . . .
C21 C 0.7856(4) 0.2602(3) 1.0300(2) 0.0551(9) Uani 1 1 d . . . . .
H21 H 0.792945 0.256304 1.096287 0.066 Uiso 1 1 calc R . . . .
C22 C 0.6411(3) 0.2866(3) 1.0160(2) 0.0434(7) Uani 1 1 d . . . . .
H22 H 0.551775 0.300568 1.072928 0.052 Uiso 1 1 calc R . . . .
C23 C 0.3473(3) 0.2797(3) 0.9868(2) 0.0381(7) Uani 1 1 d . . . . .
C24 C 0.3412(4) 0.1443(3) 1.0081(2) 0.0516(8) Uani 1 1 d . . . . .
H24 H 0.415157 0.080059 0.966078 0.062 Uiso 1 1 calc R . . . .
C25 C 0.2250(5) 0.1049(4) 1.0920(3) 0.0699(11) Uani 1 1 d . . . . .
H25 H 0.221068 0.013939 1.106559 0.084 Uiso 1 1 calc R . . . .
C26 C 0.1163(4) 0.1985(5) 1.1533(3) 0.0741(12) Uani 1 1 d . . . . .
H26 H 0.039757 0.171412 1.210680 0.089 Uiso 1 1 calc R . . . .
C27 C 0.1193(4) 0.3327(4) 1.1309(3) 0.0724(11) Uani 1 1 d . . . . .
H27 H 0.043047 0.396378 1.171944 0.087 Uiso 1 1 calc R . . . .
C28 C 0.2360(3) 0.3736(3) 1.0472(2) 0.0514(8) Uani 1 1 d . . . . .
H28 H 0.238483 0.464680 1.032180 0.062 Uiso 1 1 calc R . . . .


_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 C1 1.878(3) . ?
O1 C9 1.209(4) . ?
N1 C14 1.410(3) . ?
N1 C17 1.414(3) . ?
N1 C23 1.433(3) . ?
C1 C2 1.395(4) . ?
C1 C6 1.390(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(4) . ?
C5 C6 1.380(4) . ?
C5 C9 1.484(4) . ?
C6 C7 1.507(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.509(4) . ?
C8 C9 1.492(4) . ?
C8 C10 1.344(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.449(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.406(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(4) . ?
C14 C15 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(4) . ?
C17 C22 1.398(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 C28 1.367(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.371(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.387(4) . ?
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
C14 N1 C17 123.0(2) . . ?
C14 N1 C23 118.9(2) . . ?
C17 N1 C23 117.5(2) . . ?
C2 C1 Br1 120.6(3) . . ?
C6 C1 Br1 120.5(2) . . ?
C6 C1 C2 118.8(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C9 128.1(3) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 C9 109.8(2) . . ?
C1 C6 C7 128.6(3) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 111.7(2) . . ?
C6 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C6 C7 C8 103.5(2) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C9 C8 C7 108.9(2) . . ?
C10 C8 C7 130.9(3) . . ?
C10 C8 C9 120.2(3) . . ?
O1 C9 C5 126.9(3) . . ?
O1 C9 C8 127.0(3) . . ?
C5 C9 C8 106.0(3) . . ?
C8 C10 H10 114.4 . . ?
C8 C10 C11 131.2(3) . . ?
C11 C10 H10 114.4 . . ?
C12 C11 C10 125.1(3) . . ?
C12 C11 C16 116.3(2) . . ?
C16 C11 C10 118.6(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 N1 121.7(3) . . ?
C15 C14 N1 119.9(2) . . ?
C15 C14 C13 118.4(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C18 C17 N1 122.1(2) . . ?
C18 C17 C22 118.2(3) . . ?
C22 C17 N1 119.8(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C24 C23 N1 119.2(3) . . ?
C28 C23 N1 120.8(3) . . ?
C28 C23 C24 119.9(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 119.8(3) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
