# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1427486'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 Br Cl N2'
_chemical_formula_sum            'C21 H14 Br Cl N2'
_chemical_formula_weight         409.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.9188(9)
_cell_length_b                   9.0339(15)
_cell_length_c                   16.647(3)
_cell_angle_alpha                83.228(5)
_cell_angle_beta                 87.565(5)
_cell_angle_gamma                87.189(5)
_cell_volume                     882.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    5387
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.13

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            13553
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4070
_reflns_number_gt                2704
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0601P)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         4029
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 -0.69787(5) 0.72409(3) 0.007921(16) 0.06741(15) Uani 1 1 d . . .
Cl Cl 0.71608(14) 0.60860(9) 0.65643(4) 0.0717(2) Uani 1 1 d . . .
N2 N 0.1974(3) 0.9739(2) 0.33327(12) 0.0517(5) Uani 1 1 d . . .
N1 N 0.0522(3) 0.9874(2) 0.27130(12) 0.0472(5) Uani 1 1 d . . .
C16 C -0.5092(4) 0.7740(3) 0.08921(16) 0.0485(6) Uani 1 1 d . . .
C7 C 0.0179(4) 1.1311(3) 0.22635(14) 0.0449(6) Uani 1 1 d . . .
C4 C 0.3033(4) 0.7813(3) 0.44135(15) 0.0473(6) Uani 1 1 d . . .
C1 C 0.5548(5) 0.6766(3) 0.57372(15) 0.0516(7) Uani 1 1 d . . .
C19 C -0.0666(4) 0.8622(3) 0.26988(14) 0.0438(6) Uani 1 1 d . . .
C3 C 0.5085(4) 0.8428(3) 0.45364(16) 0.0531(7) Uani 1 1 d . . .
H3 H 0.5630 0.9210 0.4157 0.064 Uiso 1 1 calc R . .
C20 C 0.1691(4) 0.8375(3) 0.37075(14) 0.0455(6) Uani 1 1 d . . .
C12 C -0.1836(5) 1.2094(3) 0.23730(17) 0.0565(7) Uani 1 1 d . . .
H12 H -0.3007 1.1666 0.2720 0.068 Uiso 1 1 calc R . .
C2 C 0.6342(5) 0.7916(3) 0.52037(17) 0.0550(7) Uani 1 1 d . . .
H2 H 0.7727 0.8352 0.5291 0.066 Uiso 1 1 calc R . .
C18 C -0.4132(4) 0.7548(3) 0.22734(15) 0.0482(6) Uani 1 1 d . . .
H18 H -0.4443 0.7184 0.2824 0.058 Uiso 1 1 calc R . .
C8 C 0.1874(5) 1.1919(3) 0.17578(17) 0.0569(7) Uani 1 1 d . . .
H8 H 0.3263 1.1370 0.1686 0.068 Uiso 1 1 calc R . .
C14 C -0.1841(4) 0.8925(3) 0.12609(15) 0.0519(6) Uani 1 1 d . . .
H14 H -0.0579 0.9520 0.1109 0.062 Uiso 1 1 calc R . .
C11 C -0.2133(5) 1.3519(3) 0.19696(19) 0.0655(8) Uani 1 1 d . . .
H11 H -0.3517 1.4075 0.2042 0.079 Uiso 1 1 calc R . .
C21 C 0.0053(4) 0.7647(3) 0.33360(15) 0.0482(6) Uani 1 1 d . . .
H21 H -0.0455 0.6670 0.3496 0.058 Uiso 1 1 calc R . .
C13 C -0.2246(4) 0.8397(3) 0.20734(15) 0.0440(6) Uani 1 1 d . . .
C10 C -0.0462(5) 1.4123(3) 0.14733(18) 0.0623(8) Uani 1 1 d . . .
H10 H -0.0677 1.5103 0.1203 0.075 Uiso 1 1 calc R . .
C17 C -0.5555(4) 0.7222(3) 0.16932(16) 0.0514(6) Uani 1 1 d . . .
H17 H -0.6842 0.6647 0.1842 0.062 Uiso 1 1 calc R . .
C6 C 0.3553(5) 0.6144(4) 0.56295(17) 0.0665(8) Uani 1 1 d . . .
H6 H 0.3027 0.5351 0.6006 0.080 Uiso 1 1 calc R . .
C15 C -0.3254(5) 0.8590(3) 0.06755(16) 0.0566(7) Uani 1 1 d . . .
H15 H -0.2955 0.8947 0.0123 0.068 Uiso 1 1 calc R . .
C5 C 0.2296(5) 0.6676(3) 0.49648(17) 0.0612(7) Uani 1 1 d . . .
H5 H 0.0899 0.6246 0.4890 0.073 Uiso 1 1 calc R . .
C9 C 0.1545(6) 1.3328(3) 0.13575(18) 0.0662(8) Uani 1 1 d . . .
H9 H 0.2699 1.3751 0.1002 0.079 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 C16 1.898(3) . ?
Cl C1 1.744(3) . ?
N2 C20 1.329(3) . ?
N2 N1 1.361(3) . ?
N1 C19 1.365(3) . ?
N1 C7 1.430(3) . ?
C16 C15 1.374(4) . ?
C16 C17 1.381(4) . ?
C7 C12 1.373(4) . ?
C7 C8 1.374(4) . ?
C4 C5 1.369(4) . ?
C4 C3 1.393(4) . ?
C4 C20 1.473(3) . ?
C1 C6 1.360(4) . ?
C1 C2 1.373(4) . ?
C19 C21 1.365(3) . ?
C19 C13 1.466(3) . ?
C3 C2 1.385(3) . ?
C20 C21 1.402(3) . ?
C12 C11 1.387(4) . ?
C18 C17 1.375(4) . ?
C18 C13 1.392(3) . ?
C8 C9 1.374(4) . ?
C14 C15 1.380(4) . ?
C14 C13 1.395(3) . ?
C11 C10 1.355(4) . ?
C10 C9 1.376(4) . ?
C6 C5 1.385(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
C20 N2 N1 104.6(2) . . ?
N2 N1 C19 112.24(19) . . ?
N2 N1 C7 118.1(2) . . ?
C19 N1 C7 128.83(19) . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 Br1 119.6(2) . . ?
C17 C16 Br1 119.7(2) . . ?
C12 C7 C8 120.8(2) . . ?
C12 C7 N1 118.7(2) . . ?
C8 C7 N1 120.4(2) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C20 120.9(2) . . ?
C3 C4 C20 120.7(2) . . ?
C6 C1 C2 121.5(2) . . ?
C6 C1 Cl 119.7(2) . . ?
C2 C1 Cl 118.8(2) . . ?
N1 C19 C21 105.8(2) . . ?
N1 C19 C13 124.8(2) . . ?
C21 C19 C13 129.2(2) . . ?
C2 C3 C4 121.0(3) . . ?
N2 C20 C21 111.1(2) . . ?
N2 C20 C4 120.3(2) . . ?
C21 C20 C4 128.6(2) . . ?
C7 C12 C11 118.9(3) . . ?
C1 C2 C3 118.6(3) . . ?
C17 C18 C13 121.6(2) . . ?
C9 C8 C7 119.5(3) . . ?
C15 C14 C13 120.7(2) . . ?
C10 C11 C12 120.4(3) . . ?
C19 C21 C20 106.2(2) . . ?
C18 C13 C14 117.9(2) . . ?
C18 C13 C19 120.0(2) . . ?
C14 C13 C19 121.9(2) . . ?
C11 C10 C9 120.5(3) . . ?
C18 C17 C16 119.2(2) . . ?
C1 C6 C5 119.4(3) . . ?
C16 C15 C14 119.9(2) . . ?
C4 C5 C6 121.1(3) . . ?
C8 C9 C10 119.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_002
_database_code_depnum_ccdc_archive 'CCDC 1433734'
_audit_update_record             
;
2015-10-28 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Br N2'
_chemical_formula_sum            'C21 H15 Br N2 '
_chemical_formula_weight         375.25

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8446(7)
_cell_length_b                   10.7346(16)
_cell_length_c                   27.540(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1727.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    5978
_cell_measurement_theta_min      2092
_cell_measurement_theta_max      23.44

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            15441
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3917
_reflns_number_gt                2662
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1324P)²+1.3947P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.00(2)
_refine_ls_number_reflns         3917
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2228
_refine_ls_wR_factor_gt          0.1993
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 -0.19422(15) -0.08397(8) 1.00949(3) 0.0734(3) Uani 1 1 d . . .
N2 N 0.6217(10) 0.1823(5) 0.8524(2) 0.0474(12) Uani 1 1 d . . .
C13 C 0.3208(12) 0.1459(6) 0.9162(2) 0.0455(14) Uani 1 1 d . . .
C6 C 0.8882(12) 0.4775(6) 0.8640(2) 0.0481(15) Uani 1 1 d . . .
C7 C 0.5852(12) 0.0737(6) 0.8229(2) 0.0467(14) Uani 1 1 d . . .
N1 N 0.7767(10) 0.2682(5) 0.83754(18) 0.0481(12) Uani 1 1 d . . .
C18 C 0.1278(12) 0.2018(6) 0.9354(2) 0.0472(15) Uani 1 1 d . . .
H18 H 0.1012 0.2879 0.9297 0.057 Uiso 1 1 calc R . .
C21 C 0.5715(12) 0.3409(6) 0.9003(2) 0.0479(15) Uani 1 1 d . . .
H21 H 0.5159 0.3954 0.9248 0.057 Uiso 1 1 calc R . .
C17 C -0.0271(12) 0.1341(7) 0.9627(2) 0.0528(16) Uani 1 1 d . . .
H17 H -0.1599 0.1730 0.9756 0.063 Uiso 1 1 calc R . .
C19 C 0.7463(12) 0.3653(6) 0.8676(2) 0.0463(15) Uani 1 1 d . . .
C14 C 0.3610(13) 0.0204(6) 0.9251(3) 0.0512(16) Uani 1 1 d . . .
H14 H 0.4945 -0.0188 0.9127 0.061 Uiso 1 1 calc R . .
C5 C 0.8273(13) 0.5851(6) 0.8885(3) 0.0592(17) Uani 1 1 d . . .
H5 H 0.6912 0.5869 0.9073 0.071 Uiso 1 1 calc R . .
C8 C 0.3787(13) 0.0617(7) 0.7987(3) 0.0555(16) Uani 1 1 d . . .
H8 H 0.2632 0.1234 0.8018 0.067 Uiso 1 1 calc R . .
C2 C 1.0891(15) 0.4794(7) 0.8368(3) 0.0626(19) Uani 1 1 d . . .
H2 H 1.1351 0.4064 0.8199 0.075 Uiso 1 1 calc R . .
C15 C 0.2035(14) -0.0475(6) 0.9524(3) 0.0564(16) Uani 1 1 d . . .
H15 H 0.2290 -0.1336 0.9581 0.068 Uiso 1 1 calc R . .
C20 C 0.4948(12) 0.2230(6) 0.8905(2) 0.0447(14) Uani 1 1 d . . .
C3 C 1.1618(16) 0.6902(8) 0.8588(3) 0.071(2) Uani 1 1 d . . .
H3 H 1.2558 0.7623 0.8574 0.085 Uiso 1 1 calc R . .
C12 C 0.7548(15) -0.0142(7) 0.8189(3) 0.064(2) Uani 1 1 d . . .
H12 H 0.8968 -0.0040 0.8352 0.077 Uiso 1 1 calc R . .
C1 C 1.2224(15) 0.5847(7) 0.8339(3) 0.071(2) Uani 1 1 d . . .
H1 H 1.3571 0.5842 0.8146 0.085 Uiso 1 1 calc R . .
C9 C 0.3439(16) -0.0434(8) 0.7696(3) 0.066(2) Uani 1 1 d . . .
H9 H 0.2042 -0.0531 0.7524 0.080 Uiso 1 1 calc R . .
C4 C 0.9651(15) 0.6908(7) 0.8855(3) 0.065(2) Uani 1 1 d . . .
H4 H 0.9215 0.7643 0.9024 0.078 Uiso 1 1 calc R . .
C16 C 0.0143(13) 0.0081(7) 0.9710(2) 0.0535(17) Uani 1 1 d . . .
C11 C 0.7125(18) -0.1193(7) 0.7901(3) 0.072(2) Uani 1 1 d . . .
H11 H 0.8261 -0.1823 0.7875 0.086 Uiso 1 1 calc R . .
C10 C 0.5118(19) -0.1326(8) 0.7659(3) 0.073(2) Uani 1 1 d . . .
H10 H 0.4871 -0.2041 0.7463 0.087 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 C16 1.894(7) . ?
N2 N1 1.356(7) . ?
N2 C20 1.358(8) . ?
N2 C7 1.437(8) . ?
C13 C18 1.382(10) . ?
C13 C14 1.390(9) . ?
C13 C20 1.490(9) . ?
C6 C5 1.385(10) . ?
C6 C2 1.392(11) . ?
C6 C19 1.466(9) . ?
C7 C12 1.373(10) . ?
C7 C8 1.385(10) . ?
N1 C19 1.342(8) . ?
C18 C17 1.384(9) . ?
C21 C20 1.369(9) . ?
C21 C19 1.388(10) . ?
C17 C16 1.393(10) . ?
C14 C15 1.395(10) . ?
C5 C4 1.394(10) . ?
C8 C9 1.399(10) . ?
C2 C1 1.374(10) . ?
C15 C16 1.356(11) . ?
C3 C4 1.365(13) . ?
C3 C1 1.370(12) . ?
C12 C11 1.401(11) . ?
C9 C10 1.375(13) . ?
C11 C10 1.356(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C20 112.3(5) . . ?
N1 N2 C7 118.7(5) . . ?
C20 N2 C7 128.1(6) . . ?
C18 C13 C14 119.5(6) . . ?
C18 C13 C20 119.8(6) . . ?
C14 C13 C20 120.5(7) . . ?
C5 C6 C2 117.8(6) . . ?
C5 C6 C19 120.5(6) . . ?
C2 C6 C19 121.7(6) . . ?
C12 C7 C8 121.8(6) . . ?
C12 C7 N2 119.8(6) . . ?
C8 C7 N2 118.5(6) . . ?
C19 N1 N2 104.7(5) . . ?
C13 C18 C17 120.9(6) . . ?
C20 C21 C19 106.7(6) . . ?
C18 C17 C16 119.1(7) . . ?
N1 C19 C21 110.6(5) . . ?
N1 C19 C6 121.4(6) . . ?
C21 C19 C6 128.0(6) . . ?
C13 C14 C15 119.3(7) . . ?
C6 C5 C4 120.2(7) . . ?
C7 C8 C9 118.5(7) . . ?
C1 C2 C6 121.4(8) . . ?
C16 C15 C14 120.8(6) . . ?
N2 C20 C21 105.7(6) . . ?
N2 C20 C13 124.2(6) . . ?
C21 C20 C13 130.0(6) . . ?
C4 C3 C1 119.4(7) . . ?
C7 C12 C11 118.2(8) . . ?
C3 C1 C2 120.3(8) . . ?
C10 C9 C8 120.0(7) . . ?
C3 C4 C5 120.9(8) . . ?
C15 C16 C17 120.4(7) . . ?
C15 C16 Br1 120.4(5) . . ?
C17 C16 Br1 119.1(6) . . ?
C10 C11 C12 121.0(9) . . ?
C11 C10 C9 120.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.156
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1457746'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl N2 '
_chemical_formula_sum            'C21 H15 Cl N2 '
_chemical_formula_weight         330.80

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I4(1)/a  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.6551(5)
_cell_length_b                   20.6551(5)
_cell_length_c                   15.9903(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6822.0(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    296
_cell_measurement_reflns_used    8259
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2752
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            14912
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3004
_reflns_number_gt                2539
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0592P)²+3.9542P] 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         2984
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Cl1 Cl 0.95977(2) 0.66909(3) 0.03107(3) 0.06021(19) Uani 1 1 d . . .
N1 N 0.85786(7) 0.61127(6) 0.17075(8) 0.0398(3) Uani 1 1 d . . .
N2 N 0.86579(7) 0.59250(7) 0.25197(8) 0.0432(4) Uani 1 1 d . . .
C4 C 0.85815(9) 0.56326(8) 0.10671(10) 0.0417(4) Uani 1 1 d . . .
C16 C 0.84304(8) 0.71347(8) 0.08527(10) 0.0388(4) Uani 1 1 d . . .
C1 C 0.86258(8) 0.64676(8) 0.29624(10) 0.0411(4) Uani 1 1 d . . .
C3 C 0.85024(8) 0.67664(8) 0.16400(10) 0.0393(4) Uani 1 1 d . . .
C10 C 0.87087(8) 0.64646(8) 0.38801(10) 0.0434(4) Uani 1 1 d . . .
C17 C 0.88980(8) 0.71520(8) 0.02263(10) 0.0415(4) Uani 1 1 d . . .
C9 C 0.81339(10) 0.56616(9) 0.04287(12) 0.0515(5) Uani 1 1 d . . .
H9 H 0.7821 0.5999 0.0413 0.062 Uiso 1 1 calc R . .
C18 C 0.88307(10) 0.75450(10) -0.04672(12) 0.0525(5) Uani 1 1 d . . .
H18 H 0.9154 0.7545 -0.0890 0.063 Uiso 1 1 calc R . .
C11 C 0.86136(9) 0.59082(9) 0.43522(11) 0.0511(5) Uani 1 1 d . . .
H11 H 0.8483 0.5518 0.4087 0.061 Uiso 1 1 calc R . .
C21 C 0.78945(9) 0.75320(9) 0.07531(12) 0.0500(4) Uani 1 1 d . . .
H21 H 0.7565 0.7530 0.1168 0.060 Uiso 1 1 calc R . .
C2 C 0.85246(9) 0.70033(8) 0.24398(10) 0.0456(4) Uani 1 1 d . . .
H2 H 0.8480 0.7442 0.2607 0.055 Uiso 1 1 calc R . .
C12 C 0.87094(10) 0.59229(11) 0.52145(12) 0.0579(5) Uani 1 1 d . . .
H12 H 0.8642 0.5541 0.5535 0.070 Uiso 1 1 calc R . .
C13 C 0.88987(10) 0.64798(11) 0.56041(12) 0.0594(5) Uani 1 1 d . . .
H13 H 0.8966 0.6484 0.6192 0.071 Uiso 1 1 calc R . .
C15 C 0.88948(10) 0.70250(10) 0.42895(12) 0.0557(5) Uani 1 1 d . . .
H15 H 0.8958 0.7411 0.3977 0.067 Uiso 1 1 calc R . .
C5 C 0.90313(11) 0.51438(10) 0.11070(13) 0.0637(6) Uani 1 1 d . . .
H5 H 0.9337 0.5127 0.1550 0.076 Uiso 1 1 calc R . .
C20 C 0.78285(10) 0.79308(10) 0.00648(13) 0.0594(5) Uani 1 1 d . . .
H20 H 0.7459 0.8202 0.0013 0.071 Uiso 1 1 calc R . .
C14 C 0.89908(11) 0.70326(11) 0.51458(12) 0.0620(5) Uani 1 1 d . . .
H14 H 0.9121 0.7421 0.5416 0.074 Uiso 1 1 calc R . .
C19 C 0.82965(11) 0.79355(10) -0.05447(13) 0.0596(5) Uani 1 1 d . . .
H19 H 0.8251 0.8209 -0.1019 0.072 Uiso 1 1 calc R . .
C8 C 0.81472(15) 0.51950(12) -0.01849(15) 0.0810(8) Uani 1 1 d . . .
H8 H 0.7845 0.5211 -0.0632 0.097 Uiso 1 1 calc R . .
C6 C 0.90299(16) 0.46784(13) 0.04904(16) 0.0952(10) Uani 1 1 d . . .
H6 H 0.9334 0.4333 0.0511 0.114 Uiso 1 1 calc R . .
C7 C 0.85924(19) 0.47098(13) -0.01537(16) 0.1071(11) Uani 1 1 d . . .
H7 H 0.8600 0.4391 -0.0581 0.129 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
Cl1 C17 1.7361(18) . ?
N1 C3 1.364(2) . ?
N1 N2 1.3651(18) . ?
N1 C4 1.426(2) . ?
N2 C1 1.327(2) . ?
C4 C5 1.373(3) . ?
C4 C9 1.379(2) . ?
C16 C21 1.387(2) . ?
C16 C17 1.392(2) . ?
C16 C3 1.478(2) . ?
C1 C2 1.402(2) . ?
C1 C10 1.477(2) . ?
C3 C2 1.370(2) . ?
C10 C15 1.384(3) . ?
C10 C11 1.389(3) . ?
C17 C18 1.381(2) . ?
C9 C8 1.376(3) . ?
C18 C19 1.372(3) . ?
C11 C12 1.393(3) . ?
C21 C20 1.381(3) . ?
C12 C13 1.365(3) . ?
C13 C14 1.370(3) . ?
C15 C14 1.384(3) . ?
C5 C6 1.377(3) . ?
C20 C19 1.373(3) . ?
C8 C7 1.361(4) . ?
C6 C7 1.372(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
C3 N1 N2 111.74(13) . . ?
C3 N1 C4 129.23(13) . . ?
N2 N1 C4 119.04(13) . . ?
C1 N2 N1 105.17(13) . . ?
C5 C4 C9 121.32(17) . . ?
C5 C4 N1 118.74(16) . . ?
C9 C4 N1 119.93(15) . . ?
C21 C16 C17 117.12(15) . . ?
C21 C16 C3 118.85(15) . . ?
C17 C16 C3 123.79(15) . . ?
N2 C1 C2 110.84(15) . . ?
N2 C1 C10 121.36(15) . . ?
C2 C1 C10 127.77(15) . . ?
N1 C3 C2 106.02(14) . . ?
N1 C3 C16 126.05(14) . . ?
C2 C3 C16 127.91(15) . . ?
C15 C10 C11 118.30(16) . . ?
C15 C10 C1 119.89(16) . . ?
C11 C10 C1 121.80(16) . . ?
C18 C17 C16 121.54(17) . . ?
C18 C17 Cl1 117.94(14) . . ?
C16 C17 Cl1 120.50(13) . . ?
C8 C9 C4 118.97(19) . . ?
C19 C18 C17 119.92(18) . . ?
C10 C11 C12 119.99(19) . . ?
C20 C21 C16 121.53(18) . . ?
C3 C2 C1 106.22(15) . . ?
C13 C12 C11 120.70(19) . . ?
C12 C13 C14 119.86(18) . . ?
C14 C15 C10 121.15(19) . . ?
C4 C5 C6 118.6(2) . . ?
C19 C20 C21 120.02(19) . . ?
C13 C14 C15 120.0(2) . . ?
C18 C19 C20 119.86(17) . . ?
C7 C8 C9 120.2(2) . . ?
C7 C6 C5 120.4(2) . . ?
C8 C7 C6 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_004
_database_code_depnum_ccdc_archive 'CCDC 1465079'
_audit_update_record             
;
2016-03-12 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 Cl N2 O'
_chemical_formula_sum            'C22 H17 Cl N2 O '
_chemical_formula_weight         360.83

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'

_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                   9.490(3)
_cell_length_b                   12.047(4)
_cell_length_c                   16.469(5)
_cell_angle_alpha                100.826(8)
_cell_angle_beta                 99.318(8)
_cell_angle_gamma                90.148(8)
_cell_volume                     1823.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6126
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      21.67

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            15240
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6439
_reflns_number_gt                2960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1196P)²+6.5725P] 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         5747
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1998
_refine_ls_R_factor_gt           0.1081
_refine_ls_wR_factor_ref         0.3159
_refine_ls_wR_factor_gt          0.2915
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.002

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
Cl1 Cl -0.0923(2) 0.45107(16) 0.06840(11) 0.0782(6) Uani 1 1 d . . .
Cl2 Cl 0.4288(2) -0.04328(18) 0.08991(11) 0.0863(6) Uani 1 1 d . . .
O2 O 0.3352(4) 0.5419(4) 0.5969(3) 0.0631(13) Uani 1 1 d . . .
O1 O 0.1937(4) 1.0244(4) 0.6057(3) 0.0652(13) Uani 1 1 d . . .
C23 C 0.3344(6) 0.1455(5) 0.3539(3) 0.0417(15) Uani 1 1 d . . .
N4 N 0.2172(5) 0.1071(4) 0.2993(3) 0.0466(13) Uani 1 1 d . . .
N2 N 0.1862(5) 0.6072(4) 0.2994(3) 0.0475(13) Uani 1 1 d . . .
N1 N 0.1305(5) 0.5102(4) 0.2471(3) 0.0474(13) Uani 1 1 d . . .
C32 C 0.3368(6) 0.2487(5) 0.4171(3) 0.0461(16) Uani 1 1 d . . .
N3 N 0.2571(5) 0.0088(4) 0.2522(3) 0.0423(12) Uani 1 1 d . . .
C10 C 0.1108(6) 0.7433(5) 0.4136(3) 0.0432(15) Uani 1 1 d . . .
C13 C 0.1586(6) 0.9313(5) 0.5440(4) 0.0489(16) Uani 1 1 d . . .
C1 C 0.0878(6) 0.6406(5) 0.3480(3) 0.0456(16) Uani 1 1 d . . .
C35 C 0.3428(6) 0.4450(5) 0.5390(3) 0.0480(16) Uani 1 1 d . . .
C34 C 0.2331(6) 0.4244(5) 0.4721(4) 0.0472(16) Uani 1 1 d . . .
H34 H 0.1603 0.4778 0.4670 0.057 Uiso 1 1 calc R . .
C36 C 0.4531(6) 0.3705(5) 0.5454(4) 0.0502(17) Uani 1 1 d . . .
H36 H 0.5308 0.3845 0.5907 0.060 Uiso 1 1 calc R . .
C26 C 0.1492(6) -0.0575(5) 0.1904(3) 0.0463(16) Uani 1 1 d . . .
C37 C 0.4452(7) 0.2750(5) 0.4832(4) 0.0588(19) Uani 1 1 d . . .
H37 H 0.5211 0.2239 0.4869 0.071 Uiso 1 1 calc R . .
C25 C 0.3962(6) -0.0130(5) 0.2770(4) 0.0475(16) Uani 1 1 d . . .
C33 C 0.2276(6) 0.3260(5) 0.4118(4) 0.0481(16) Uani 1 1 d . . .
H33 H 0.1495 0.3113 0.3668 0.058 Uiso 1 1 calc R . .
C3 C -0.0007(6) 0.4812(5) 0.2623(4) 0.0473(16) Uani 1 1 d . . .
C15 C 0.0296(7) 0.7614(5) 0.4757(4) 0.0569(18) Uani 1 1 d . . .
H15 H -0.0440 0.7072 0.4745 0.068 Uiso 1 1 calc R . .
C17 C -0.0866(6) 0.3806(5) 0.2173(4) 0.0486(17) Uani 1 1 d . . .
C4 C 0.2179(6) 0.4489(5) 0.1937(4) 0.0511(17) Uani 1 1 d . . .
C18 C -0.1349(6) 0.3566(5) 0.1294(4) 0.061(2) Uani 1 1 d . . .
C14 C 0.0488(7) 0.8536(5) 0.5398(4) 0.0599(19) Uani 1 1 d . . .
H14 H -0.0123 0.8640 0.5808 0.072 Uiso 1 1 calc R . .
C39 C 0.4740(6) -0.1104(5) 0.2403(4) 0.0457(16) Uani 1 1 d . . .
C9 C 0.2291(7) 0.3333(6) 0.1879(4) 0.0594(19) Uani 1 1 d . . .
H9 H 0.1726 0.2940 0.2167 0.071 Uiso 1 1 calc R . .
C24 C 0.4473(6) 0.0731(5) 0.3415(3) 0.0475(16) Uani 1 1 d . . .
H24 H 0.5416 0.0822 0.3723 0.057 Uiso 1 1 calc R . .
C2 C -0.0301(6) 0.5639(5) 0.3249(4) 0.0502(17) Uani 1 1 d . . .
H2 H -0.1150 0.5690 0.3489 0.060 Uiso 1 1 calc R . .
C12 C 0.2416(6) 0.9154(5) 0.4812(4) 0.0528(17) Uani 1 1 d . . .
H12 H 0.3155 0.9693 0.4824 0.063 Uiso 1 1 calc R . .
C31 C 0.1432(6) -0.1738(5) 0.1847(4) 0.0525(17) Uani 1 1 d . . .
H31 H 0.2075 -0.2096 0.2213 0.063 Uiso 1 1 calc R . .
C11 C 0.2186(6) 0.8228(5) 0.4174(4) 0.0508(17) Uani 1 1 d . . .
H11 H 0.2773 0.8131 0.3752 0.061 Uiso 1 1 calc R . .
C27 C 0.0528(7) -0.0043(6) 0.1406(4) 0.064(2) Uani 1 1 d . . .
H27 H 0.0570 0.0756 0.1464 0.076 Uiso 1 1 calc R . .
C16 C 0.1060(7) 1.0455(6) 0.6708(4) 0.069(2) Uani 1 1 d . . .
H16A H 0.0050 1.0403 0.6452 0.103 Uiso 1 1 calc R . .
H16B H 0.1291 1.1214 0.7045 0.103 Uiso 1 1 calc R . .
H16C H 0.1245 0.9892 0.7068 0.103 Uiso 1 1 calc R . .
C22 C -0.1355(7) 0.3065(6) 0.2623(5) 0.064(2) Uani 1 1 d . . .
H22 H -0.1099 0.3204 0.3216 0.077 Uiso 1 1 calc R . .
C29 C -0.0532(7) -0.1871(7) 0.0728(4) 0.075(2) Uani 1 1 d . . .
H29 H -0.1213 -0.2322 0.0308 0.090 Uiso 1 1 calc R . .
C30 C 0.0400(7) -0.2363(6) 0.1234(4) 0.066(2) Uani 1 1 d . . .
H30 H 0.0359 -0.3163 0.1175 0.079 Uiso 1 1 calc R . .
C38 C 0.4494(7) 0.5701(6) 0.6657(4) 0.070(2) Uani 1 1 d . . .
H38A H 0.4523 0.5134 0.7014 0.105 Uiso 1 1 calc R . .
H38B H 0.4344 0.6447 0.6984 0.105 Uiso 1 1 calc R . .
H38C H 0.5400 0.5718 0.6446 0.105 Uiso 1 1 calc R . .
C19 C -0.2121(7) 0.2593(6) 0.0892(5) 0.068(2) Uani 1 1 d . . .
H19 H -0.2345 0.2424 0.0298 0.082 Uiso 1 1 calc R . .
C28 C -0.0510(8) -0.0691(6) 0.0815(4) 0.071(2) Uani 1 1 d . . .
H28 H -0.1200 -0.0337 0.0472 0.085 Uiso 1 1 calc R . .
C40 C 0.4961(7) -0.1316(6) 0.1583(4) 0.064(2) Uani 1 1 d . . .
C8 C 0.3216(7) 0.2752(7) 0.1407(4) 0.077(2) Uani 1 1 d . . .
H8 H 0.3271 0.1954 0.1345 0.093 Uiso 1 1 calc R . .
C5 C 0.3026(7) 0.5073(6) 0.1531(4) 0.066(2) Uani 1 1 d . . .
H5 H 0.2981 0.5872 0.1594 0.080 Uiso 1 1 calc R . .
C44 C 0.5376(6) -0.1809(6) 0.2929(4) 0.0615(19) Uani 1 1 d . . .
H44 H 0.5241 -0.1674 0.3498 0.074 Uiso 1 1 calc R . .
C41 C 0.5779(9) -0.2223(7) 0.1293(5) 0.090(3) Uani 1 1 d . . .
H41 H 0.5904 -0.2380 0.0723 0.108 Uiso 1 1 calc R . .
C20 C -0.2562(7) 0.1873(6) 0.1358(5) 0.079(2) Uani 1 1 d . . .
H20 H -0.3106 0.1205 0.1086 0.095 Uiso 1 1 calc R . .
C21 C -0.2222(7) 0.2111(6) 0.2217(6) 0.081(2) Uani 1 1 d . . .
H21 H -0.2575 0.1628 0.2538 0.097 Uiso 1 1 calc R . .
C6 C 0.3925(7) 0.4500(7) 0.1040(5) 0.086(3) Uani 1 1 d . . .
H6 H 0.4438 0.4884 0.0720 0.104 Uiso 1 1 calc R . .
C7 C 0.4072(7) 0.3361(8) 0.1019(4) 0.086(3) Uani 1 1 d . . .
H7 H 0.4776 0.2978 0.0733 0.103 Uiso 1 1 calc R . .
C43 C 0.6199(7) -0.2702(6) 0.2642(5) 0.075(2) Uani 1 1 d . . .
H43 H 0.6615 -0.3176 0.3009 0.090 Uiso 1 1 calc R . .
C42 C 0.6403(9) -0.2890(7) 0.1837(6) 0.095(3) Uani 1 1 d . . .
H42 H 0.6985 -0.3489 0.1642 0.114 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
Cl1 C18 1.740(7) . ?
Cl2 C40 1.740(7) . ?
O2 C35 1.372(7) . ?
O2 C38 1.425(7) . ?
O1 C13 1.365(7) . ?
O1 C16 1.447(8) . ?
C23 N4 1.334(6) . ?
C23 C24 1.399(8) . ?
C23 C32 1.461(8) . ?
N4 N3 1.378(6) . ?
N2 C1 1.340(7) . ?
N2 N1 1.363(6) . ?
N1 C3 1.366(7) . ?
N1 C4 1.415(7) . ?
C32 C37 1.360(8) . ?
C32 C33 1.399(8) . ?
N3 C25 1.359(7) . ?
N3 C26 1.440(7) . ?
C10 C15 1.363(8) . ?
C10 C11 1.386(8) . ?
C10 C1 1.473(8) . ?
C13 C12 1.384(8) . ?
C13 C14 1.383(8) . ?
C1 C2 1.406(8) . ?
C35 C34 1.372(8) . ?
C35 C36 1.384(8) . ?
C34 C33 1.392(8) . ?
C36 C37 1.383(8) . ?
C26 C27 1.371(8) . ?
C26 C31 1.386(8) . ?
C25 C24 1.363(7) . ?
C25 C39 1.473(8) . ?
C3 C2 1.357(8) . ?
C3 C17 1.464(8) . ?
C15 C14 1.371(8) . ?
C17 C22 1.386(9) . ?
C17 C18 1.419(9) . ?
C4 C9 1.383(9) . ?
C4 C5 1.392(9) . ?
C18 C19 1.378(9) . ?
C39 C40 1.377(8) . ?
C39 C44 1.396(9) . ?
C9 C8 1.373(9) . ?
C12 C11 1.371(8) . ?
C31 C30 1.391(8) . ?
C27 C28 1.388(9) . ?
C22 C21 1.404(9) . ?
C29 C30 1.334(10) . ?
C29 C28 1.402(10) . ?
C19 C20 1.366(10) . ?
C40 C41 1.397(10) . ?
C8 C7 1.396(11) . ?
C5 C6 1.369(9) . ?
C44 C43 1.387(9) . ?
C41 C42 1.378(12) . ?
C20 C21 1.374(11) . ?
C6 C7 1.374(11) . ?
C43 C42 1.348(11) . ?

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
C35 O2 C38 118.5(5) . . ?
C13 O1 C16 117.3(5) . . ?
N4 C23 C24 110.4(5) . . ?
N4 C23 C32 122.3(5) . . ?
C24 C23 C32 127.3(5) . . ?
C23 N4 N3 104.8(4) . . ?
C1 N2 N1 105.5(4) . . ?
N2 N1 C3 111.8(4) . . ?
N2 N1 C4 118.2(4) . . ?
C3 N1 C4 129.5(5) . . ?
C37 C32 C33 116.7(5) . . ?
C37 C32 C23 122.0(5) . . ?
C33 C32 C23 121.3(5) . . ?
C25 N3 N4 111.7(4) . . ?
C25 N3 C26 130.0(5) . . ?
N4 N3 C26 118.2(4) . . ?
C15 C10 C11 117.2(5) . . ?
C15 C10 C1 120.8(5) . . ?
C11 C10 C1 122.0(5) . . ?
O1 C13 C12 115.9(5) . . ?
O1 C13 C14 125.4(5) . . ?
C12 C13 C14 118.7(5) . . ?
N2 C1 C2 109.3(5) . . ?
N2 C1 C10 121.5(5) . . ?
C2 C1 C10 129.2(5) . . ?
C34 C35 O2 116.1(5) . . ?
C34 C35 C36 120.4(5) . . ?
O2 C35 C36 123.5(5) . . ?
C35 C34 C33 120.6(5) . . ?
C37 C36 C35 117.2(5) . . ?
C27 C26 C31 121.6(5) . . ?
C27 C26 N3 119.4(5) . . ?
C31 C26 N3 118.9(5) . . ?
C32 C37 C36 124.8(6) . . ?
N3 C25 C24 106.0(5) . . ?
N3 C25 C39 126.2(5) . . ?
C24 C25 C39 127.8(5) . . ?
C34 C33 C32 120.2(5) . . ?
C2 C3 N1 105.7(5) . . ?
C2 C3 C17 129.6(5) . . ?
N1 C3 C17 124.7(5) . . ?
C10 C15 C14 123.4(6) . . ?
C22 C17 C18 115.9(6) . . ?
C22 C17 C3 119.4(6) . . ?
C18 C17 C3 124.6(6) . . ?
C9 C4 C5 120.1(6) . . ?
C9 C4 N1 120.3(6) . . ?
C5 C4 N1 119.3(6) . . ?
C19 C18 C17 122.7(7) . . ?
C19 C18 Cl1 117.8(6) . . ?
C17 C18 Cl1 119.5(5) . . ?
C15 C14 C13 119.0(6) . . ?
C40 C39 C44 117.9(6) . . ?
C40 C39 C25 123.8(6) . . ?
C44 C39 C25 118.2(5) . . ?
C8 C9 C4 120.2(7) . . ?
C25 C24 C23 107.1(5) . . ?
C3 C2 C1 107.6(5) . . ?
C11 C12 C13 120.9(5) . . ?
C26 C31 C30 117.8(6) . . ?
C12 C11 C10 120.9(5) . . ?
C26 C27 C28 118.9(6) . . ?
C17 C22 C21 121.1(7) . . ?
C30 C29 C28 120.1(6) . . ?
C29 C30 C31 121.8(7) . . ?
C20 C19 C18 119.2(7) . . ?
C27 C28 C29 119.5(6) . . ?
C39 C40 C41 120.3(7) . . ?
C39 C40 Cl2 120.9(5) . . ?
C41 C40 Cl2 118.8(6) . . ?
C9 C8 C7 118.5(7) . . ?
C6 C5 C4 120.2(7) . . ?
C43 C44 C39 121.6(6) . . ?
C42 C41 C40 119.9(7) . . ?
C19 C20 C21 120.3(7) . . ?
C20 C21 C22 120.3(7) . . ?
C5 C6 C7 118.8(7) . . ?
C6 C7 C8 121.8(7) . . ?
C42 C43 C44 119.4(7) . . ?
C43 C42 C41 120.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.893
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1473251'
_audit_update_record             
;
2016-04-10 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 Br Cl2 N2'
_chemical_formula_sum            'C21 H13 Br Cl2 N2'
_chemical_formula_weight         444.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   9.1743(6)
_cell_length_b                   12.4421(9)
_cell_length_c                   16.5980(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1894.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6583
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            14820
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3117
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1386P)²+3.0022P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.95(2)
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2118
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Br1 Br 0.31753(9) 0.77856(10) 1.17309(6) 0.0762(4) Uani 1 1 d . . .
C2 C 0.8117(7) 1.0538(6) 0.9278(5) 0.0439(17) Uani 1 1 d . . .
H2 H 0.7547 1.1134 0.9446 0.053 Uiso 1 1 calc R . .
N1 N 0.9055(7) 0.8919(5) 0.9134(4) 0.0447(14) Uani 1 1 d . . .
C1 C 0.9235(8) 1.0528(6) 0.8693(5) 0.0458(18) Uani 1 1 d . . .
C10 C 0.9624(8) 0.7866(6) 0.9274(5) 0.0448(18) Uani 1 1 d . . .
C4 C 0.6966(8) 0.9026(7) 1.0104(5) 0.0467(18) Uani 1 1 d . . .
N2 N 0.9795(7) 0.9556(5) 0.8600(4) 0.0471(15) Uani 1 1 d . . .
C8 C 0.5281(10) 0.7628(7) 1.0485(5) 0.052(2) Uani 1 1 d . . .
H8 H 0.4892 0.6929 1.0402 0.063 Uiso 1 1 calc R . .
C16 C 0.9813(8) 1.1452(6) 0.8237(5) 0.0419(17) Uani 1 1 d . . .
C6 C 0.5311(11) 0.9284(9) 1.1220(6) 0.064(2) Uani 1 1 d . . .
H6 H 0.4938 0.9723 1.1640 0.077 Uiso 1 1 calc R . .
C7 C 0.4753(9) 0.8278(8) 1.1091(5) 0.053(2) Uani 1 1 d . . .
C17 C 0.9184(11) 1.2459(7) 0.8293(6) 0.055(2) Uani 1 1 d . . .
H17 H 0.8344 1.2558 0.8619 0.066 Uiso 1 1 calc R . .
C11 C 0.9949(11) 0.7546(7) 1.0038(6) 0.059(2) Uani 1 1 d . . .
H11 H 0.9694 0.7985 1.0485 0.070 Uiso 1 1 calc R . .
C9 C 0.6391(9) 0.8017(6) 0.9999(5) 0.0485(18) Uani 1 1 d . . .
H9 H 0.6765 0.7572 0.9582 0.058 Uiso 1 1 calc R . .
C3 C 0.8033(7) 0.9496(6) 0.9551(5) 0.0422(17) Uani 1 1 d . . .
C5 C 0.6421(9) 0.9655(7) 1.0731(5) 0.055(2) Uani 1 1 d . . .
H5 H 0.6819 1.0349 1.0823 0.067 Uiso 1 1 calc R . .
C15 C 0.9956(10) 0.7235(6) 0.8616(6) 0.056(2) Uani 1 1 d . . .
H15 H 0.9701 0.7464 0.8089 0.067 Uiso 1 1 calc R . .
C13 C 1.1009(10) 0.5950(7) 0.9501(7) 0.062(2) Uani 1 1 d . . .
C14 C 1.0662(10) 0.6265(7) 0.8732(7) 0.063(2) Uani 1 1 d . . .
H14 H 1.0904 0.5822 0.8285 0.076 Uiso 1 1 calc R . .
C20 C 1.1628(11) 1.2189(8) 0.7348(7) 0.066(3) Uani 1 1 d . . .
H20 H 1.2465 1.2095 0.7018 0.079 Uiso 1 1 calc R . .
C21 C 1.1053(10) 1.1340(7) 0.7755(5) 0.054(2) Uani 1 1 d . . .
H21 H 1.1505 1.0655 0.7710 0.065 Uiso 1 1 calc R . .
C18 C 0.9766(12) 1.3329(8) 0.7878(6) 0.067(3) Uani 1 1 d . . .
H18 H 0.9322 1.4017 0.7912 0.080 Uiso 1 1 calc R . .
Cl1 Cl 1.1736(4) 1.4281(3) 0.6910(2) 0.1035(12) Uani 1 1 d . . .
Cl2 Cl 1.2019(4) 0.4774(2) 0.9636(3) 0.1109(13) Uani 1 1 d . . .
C19 C 1.0989(12) 1.3180(8) 0.7419(6) 0.066(3) Uani 1 1 d . . .
C12 C 1.0654(10) 0.6572(8) 1.0157(7) 0.067(3) Uani 1 1 d . . .
H12 H 1.0889 0.6338 1.0686 0.081 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 C7 1.897(8) . ?
C2 C3 1.375(12) . ?
C2 C1 1.413(11) . ?
N1 C3 1.369(10) . ?
N1 N2 1.369(9) . ?
N1 C10 1.429(10) . ?
C1 N2 1.323(11) . ?
C1 C16 1.475(12) . ?
C10 C11 1.362(13) . ?
C10 C15 1.379(12) . ?
C4 C9 1.374(12) . ?
C4 C5 1.395(12) . ?
C4 C3 1.463(11) . ?
C8 C7 1.377(13) . ?
C8 C9 1.386(13) . ?
C16 C17 1.383(12) . ?
C16 C21 1.398(12) . ?
C6 C7 1.370(14) . ?
C6 C5 1.382(13) . ?
C17 C18 1.390(15) . ?
C11 C12 1.388(13) . ?
C15 C14 1.383(13) . ?
C13 C14 1.373(15) . ?
C13 C12 1.375(15) . ?
C13 Cl2 1.746(9) . ?
C20 C21 1.360(14) . ?
C20 C19 1.371(15) . ?
C18 C19 1.369(15) . ?
Cl1 C19 1.749(10) . ?

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 C2 C1 105.0(7) . . ?
C3 N1 N2 111.3(6) . . ?
C3 N1 C10 130.4(7) . . ?
N2 N1 C10 117.0(6) . . ?
N2 C1 C2 111.7(7) . . ?
N2 C1 C16 120.9(7) . . ?
C2 C1 C16 127.4(7) . . ?
C11 C10 C15 121.5(7) . . ?
C11 C10 N1 120.0(7) . . ?
C15 C10 N1 118.3(7) . . ?
C9 C4 C5 118.0(8) . . ?
C9 C4 C3 122.9(8) . . ?
C5 C4 C3 118.9(7) . . ?
C1 N2 N1 105.1(6) . . ?
C7 C8 C9 118.6(8) . . ?
C17 C16 C21 118.0(8) . . ?
C17 C16 C1 121.4(8) . . ?
C21 C16 C1 120.6(7) . . ?
C7 C6 C5 119.3(8) . . ?
C6 C7 C8 121.3(8) . . ?
C6 C7 Br1 119.5(7) . . ?
C8 C7 Br1 119.2(7) . . ?
C16 C17 C18 120.8(10) . . ?
C10 C11 C12 119.4(9) . . ?
C4 C9 C8 121.9(8) . . ?
N1 C3 C2 106.8(7) . . ?
N1 C3 C4 124.5(7) . . ?
C2 C3 C4 128.3(7) . . ?
C6 C5 C4 121.0(8) . . ?
C10 C15 C14 119.4(9) . . ?
C14 C13 C12 121.4(8) . . ?
C14 C13 Cl2 118.8(8) . . ?
C12 C13 Cl2 119.7(8) . . ?
C13 C14 C15 119.1(9) . . ?
C21 C20 C19 119.4(10) . . ?
C20 C21 C16 121.5(8) . . ?
C19 C18 C17 119.1(9) . . ?
C18 C19 C20 121.3(9) . . ?
C18 C19 Cl1 118.9(8) . . ?
C20 C19 Cl1 119.7(8) . . ?
C13 C12 C11 119.3(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.092
