# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1573611'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.	2019-04-09 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 H12 Br N'
_chemical_formula_weight         322.20

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   8.5054(6)
_cell_length_b                   20.5271(17)
_cell_length_c                   8.6640(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.3042(17)
_cell_angle_gamma                90.00
_cell_volume                     1436.12(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2058
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      21.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    2.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_T_max  0.7636
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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  'Bruker Smart Aepex CCD'
_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            12467
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.51
_reflns_number_total             3610
_reflns_number_gt                2640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0426P)²+1.6642P] 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         3610
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.34511(6) 0.46475(3) 0.59665(5) 0.0862(2) Uani 1 1 d . . .
C1 C 0.0950(4) 0.64823(14) 1.1524(3) 0.0407(6) Uani 1 1 d . . .
C2 C 0.2625(4) 0.64760(16) 1.2408(4) 0.0495(7) Uani 1 1 d . . .
H2 H 0.3395 0.6273 1.2008 0.059 Uiso 1 1 calc R . .
C3 C 0.3099(5) 0.67814(18) 1.3892(4) 0.0609(9) Uani 1 1 d . . .
H3 H 0.4215 0.6785 1.4504 0.073 Uiso 1 1 calc R . .
C4 C 0.1970(5) 0.70828(18) 1.4504(4) 0.0674(10) Uani 1 1 d . . .
H4 H 0.2334 0.7281 1.5520 0.081 Uiso 1 1 calc R . .
C5 C 0.0312(5) 0.70937(16) 1.3628(4) 0.0586(9) Uani 1 1 d . . .
H5 H -0.0443 0.7300 1.4043 0.070 Uiso 1 1 calc R . .
C6 C -0.0219(4) 0.67927(13) 1.2116(4) 0.0443(6) Uani 1 1 d . . .
C7 C -0.1808(4) 0.67222(14) 1.0880(4) 0.0470(7) Uani 1 1 d . . .
C8 C -0.3425(4) 0.68971(17) 1.0783(5) 0.0614(9) Uani 1 1 d . . .
H8 H -0.3633 0.7128 1.1621 0.074 Uiso 1 1 calc R . .
C9 C -0.4698(4) 0.67218(19) 0.9429(5) 0.0676(10) Uani 1 1 d . . .
H9 H -0.5778 0.6834 0.9356 0.081 Uiso 1 1 calc R . .
C10 C -0.4406(4) 0.63820(19) 0.8173(5) 0.0630(9) Uani 1 1 d . . .
H10 H -0.5296 0.6271 0.7271 0.076 Uiso 1 1 calc R . .
C11 C -0.2828(4) 0.62027(17) 0.8217(4) 0.0517(7) Uani 1 1 d . . .
H11 H -0.2639 0.5975 0.7365 0.062 Uiso 1 1 calc R . .
C12 C -0.1535(3) 0.63768(14) 0.9590(4) 0.0417(6) Uani 1 1 d . . .
C13 C 0.0897(3) 0.58569(14) 0.9036(3) 0.0389(6) Uani 1 1 d . . .
C14 C 0.0628(4) 0.60136(16) 0.7418(4) 0.0478(7) Uani 1 1 d . . .
H14 H -0.0032 0.6369 0.6958 0.057 Uiso 1 1 calc R . .
C15 C 0.1346(4) 0.56401(18) 0.6484(4) 0.0538(8) Uani 1 1 d . . .
H15 H 0.1143 0.5734 0.5389 0.065 Uiso 1 1 calc R . .
C16 C 0.1907(4) 0.53368(14) 0.9724(4) 0.0447(6) Uani 1 1 d . . .
H16 H 0.2077 0.5229 1.0807 0.054 Uiso 1 1 calc R . .
C17 C 0.2667(4) 0.49762(16) 0.8814(4) 0.0491(7) Uani 1 1 d . . .
H17 H 0.3375 0.4635 0.9286 0.059 Uiso 1 1 calc R . .
C18 C 0.2361(4) 0.51285(16) 0.7196(4) 0.0496(7) Uani 1 1 d . . .
N1 N 0.0148(3) 0.62328(12) 0.9989(3) 0.0416(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0778(3) 0.1160(4) 0.0774(3) -0.0288(2) 0.0427(2) 0.0180(2)
C1 0.0493(16) 0.0350(15) 0.0398(14) -0.0016(11) 0.0171(12) -0.0034(11)
C2 0.0515(17) 0.0475(18) 0.0484(17) -0.0003(14) 0.0144(13) -0.0041(13)
C3 0.069(2) 0.055(2) 0.0508(18) -0.0045(16) 0.0071(16) -0.0118(17)
C4 0.097(3) 0.051(2) 0.0505(19) -0.0165(16) 0.0183(19) -0.0132(19)
C5 0.086(3) 0.0391(17) 0.0579(19) -0.0095(15) 0.0329(18) -0.0004(16)
C6 0.0590(18) 0.0292(14) 0.0505(16) 0.0021(12) 0.0254(14) 0.0006(12)
C7 0.0569(18) 0.0323(15) 0.0595(18) 0.0048(13) 0.0294(15) 0.0039(12)
C8 0.062(2) 0.0491(19) 0.085(3) 0.0037(18) 0.041(2) 0.0134(16)
C9 0.0451(19) 0.065(2) 0.096(3) 0.015(2) 0.0274(19) 0.0157(16)
C10 0.0446(18) 0.069(2) 0.071(2) 0.0173(19) 0.0122(16) 0.0042(16)
C11 0.0480(17) 0.058(2) 0.0490(17) 0.0025(15) 0.0158(13) 0.0008(14)
C12 0.0410(14) 0.0393(15) 0.0486(16) 0.0057(12) 0.0195(12) 0.0033(11)
C13 0.0375(13) 0.0418(15) 0.0409(14) -0.0043(12) 0.0174(11) -0.0046(11)
C14 0.0451(16) 0.0551(19) 0.0450(16) 0.0016(14) 0.0167(12) 0.0031(13)
C15 0.0497(17) 0.073(2) 0.0428(16) -0.0055(15) 0.0203(13) -0.0049(15)
C16 0.0504(16) 0.0437(17) 0.0442(15) 0.0011(13) 0.0208(12) 0.0000(12)
C17 0.0473(16) 0.0451(17) 0.0600(19) -0.0019(15) 0.0244(14) 0.0015(13)
C18 0.0423(15) 0.060(2) 0.0552(17) -0.0163(15) 0.0270(13) -0.0054(13)
N1 0.0407(12) 0.0457(14) 0.0401(12) -0.0046(10) 0.0150(10) 0.0018(10)

_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 C18 1.894(3) . ?
C1 N1 1.388(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.372(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(4) . ?
C7 C8 1.398(4) . ?
C7 C12 1.403(4) . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.394(4) . ?
C13 C16 1.383(4) . ?
C13 C14 1.386(4) . ?
C13 N1 1.419(3) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 C18 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(5) . ?
C17 H17 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
N1 C1 C2 129.4(3) . . ?
N1 C1 C6 109.0(3) . . ?
C2 C1 C6 121.6(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 134.0(3) . . ?
C1 C6 C7 106.8(3) . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 C6 133.9(3) . . ?
C12 C7 C6 106.9(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 117.2(3) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 N1 129.2(3) . . ?
C11 C12 C7 121.8(3) . . ?
N1 C12 C7 108.9(3) . . ?
C16 C13 C14 119.9(3) . . ?
C16 C13 N1 120.0(2) . . ?
C14 C13 N1 120.1(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C18 C15 C14 119.3(3) . . ?
C18 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C13 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C13 C16 H16 119.8 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C15 C18 C17 121.4(3) . . ?
C15 C18 Br1 119.6(2) . . ?
C17 C18 Br1 118.9(2) . . ?
C1 N1 C12 108.4(2) . . ?
C1 N1 C13 125.7(2) . . ?
C12 N1 C13 125.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.51
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.055
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1573612'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Br N'
_chemical_formula_sum            'C18 H12 Br N'
_chemical_formula_weight         322.20

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'
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   P21/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                   14.1421(15)
_cell_length_b                   5.0957(5)
_cell_length_c                   19.509(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.673(2)
_cell_angle_gamma                90.00
_cell_volume                     1381.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2358
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      21.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    2.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker Smart Aepex CCD'
_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            11165
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.38
_reflns_number_total             3379
_reflns_number_gt                3181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0610P)²+7.1349P] 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         3379
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.39611(2) 0.27896(8) 0.040245(18) 0.02324(14) Uani 1 1 d . . .
C17 C 0.5018(2) 0.3926(7) 0.10884(16) 0.0162(6) Uani 1 1 d . . .
C2 C 0.7785(2) 0.1484(7) 0.05651(16) 0.0156(6) Uani 1 1 d . . .
H2 H 0.7325 0.2776 0.0379 0.019 Uiso 1 1 calc R . .
N1 N 0.74913(19) 0.1768(5) 0.17996(14) 0.0128(5) Uani 1 1 d . . .
C13 C 0.6625(2) 0.3245(6) 0.16983(16) 0.0123(5) Uani 1 1 d . . .
C10 C 0.8201(2) -0.0755(7) 0.36136(16) 0.0169(6) Uani 1 1 d . . .
H10 H 0.8070 -0.0601 0.4072 0.020 Uiso 1 1 calc R . .
C14 C 0.6525(2) 0.5357(6) 0.21311(17) 0.0159(6) Uani 1 1 d . . .
H14 H 0.7042 0.5837 0.2494 0.019 Uiso 1 1 calc R . .
C15 C 0.5671(3) 0.6761(6) 0.2033(2) 0.0200(7) Uani 1 1 d . . .
H15 H 0.5604 0.8199 0.2330 0.024 Uiso 1 1 calc R . .
C6 C 0.8626(2) -0.1109(6) 0.15519(15) 0.0124(5) Uani 1 1 d . . .
C1 C 0.7927(2) 0.0768(6) 0.12653(15) 0.0117(5) Uani 1 1 d . . .
C7 C 0.8607(2) -0.1259(6) 0.22879(15) 0.0116(5) Uani 1 1 d . . .
C8 C 0.9107(2) -0.2824(7) 0.28222(17) 0.0159(6) Uani 1 1 d . . .
H8 H 0.9579 -0.4039 0.2733 0.019 Uiso 1 1 calc R . .
C16 C 0.4910(2) 0.6079(7) 0.15012(18) 0.0188(6) Uani 1 1 d . . .
H16 H 0.4330 0.7066 0.1424 0.023 Uiso 1 1 calc R . .
C11 C 0.7698(2) 0.0814(6) 0.30913(16) 0.0151(6) Uani 1 1 d . . .
H11 H 0.7226 0.2024 0.3184 0.018 Uiso 1 1 calc R . .
C12 C 0.7909(2) 0.0550(6) 0.24239(15) 0.0119(5) Uani 1 1 d . . .
C3 C 0.8346(2) 0.0226(7) 0.01510(16) 0.0174(6) Uani 1 1 d . . .
H3 H 0.8262 0.0665 -0.0330 0.021 Uiso 1 1 calc R . .
C5 C 0.9172(2) -0.2355(6) 0.11235(17) 0.0147(6) Uani 1 1 d . . .
H5 H 0.9633 -0.3649 0.1308 0.018 Uiso 1 1 calc R . .
C9 C 0.8897(2) -0.2563(7) 0.34898(18) 0.0176(6) Uani 1 1 d . . .
H9 H 0.9227 -0.3611 0.3861 0.021 Uiso 1 1 calc R . .
C18 C 0.5862(2) 0.2486(6) 0.11740(17) 0.0145(6) Uani 1 1 d . . .
H18 H 0.5920 0.1020 0.0884 0.017 Uiso 1 1 calc R . .
C4 C 0.9032(2) -0.1675(7) 0.04224(17) 0.0183(6) Uani 1 1 d . . .
H4 H 0.9403 -0.2502 0.0125 0.022 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01448(19) 0.0326(2) 0.0213(2) 0.00308(14) -0.00017(12) 0.00507(13)
C17 0.0137(14) 0.0188(15) 0.0161(14) 0.0067(12) 0.0032(11) 0.0021(12)
C2 0.0163(14) 0.0159(14) 0.0144(14) 0.0021(11) 0.0020(11) 0.0030(12)
N1 0.0135(12) 0.0126(12) 0.0127(12) 0.0001(9) 0.0037(9) 0.0023(10)
C13 0.0113(13) 0.0095(13) 0.0173(14) 0.0028(11) 0.0060(11) 0.0014(10)
C10 0.0170(14) 0.0213(15) 0.0132(13) -0.0008(12) 0.0050(11) -0.0034(12)
C14 0.0190(15) 0.0099(13) 0.0202(14) -0.0011(11) 0.0074(12) -0.0023(11)
C15 0.0255(17) 0.0083(13) 0.0306(18) 0.0007(12) 0.0170(14) 0.0042(12)
C6 0.0108(12) 0.0143(13) 0.0119(13) -0.0012(11) 0.0017(10) -0.0018(11)
C1 0.0115(13) 0.0114(13) 0.0121(13) -0.0009(10) 0.0020(10) -0.0013(10)
C7 0.0092(12) 0.0128(13) 0.0130(13) 0.0001(11) 0.0028(10) -0.0010(10)
C8 0.0140(14) 0.0186(15) 0.0151(14) 0.0024(12) 0.0032(11) 0.0023(11)
C16 0.0170(15) 0.0160(15) 0.0260(16) 0.0072(13) 0.0110(12) 0.0065(12)
C11 0.0153(14) 0.0157(14) 0.0150(14) -0.0012(11) 0.0052(11) 0.0001(11)
C12 0.0112(12) 0.0110(13) 0.0132(13) -0.0009(10) 0.0017(10) -0.0026(10)
C3 0.0185(14) 0.0228(16) 0.0115(13) 0.0010(12) 0.0040(11) 0.0011(13)
C5 0.0117(13) 0.0174(14) 0.0160(14) -0.0008(11) 0.0048(11) 0.0011(11)
C9 0.0172(15) 0.0205(15) 0.0151(14) 0.0060(12) 0.0033(12) 0.0007(12)
C18 0.0158(15) 0.0137(14) 0.0148(14) 0.0022(11) 0.0052(11) 0.0011(11)
C4 0.0195(15) 0.0211(16) 0.0152(14) -0.0038(12) 0.0057(12) 0.0005(13)

_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 C17 1.903(3) . ?
C17 C16 1.386(5) . ?
C17 C18 1.384(4) . ?
C2 C3 1.389(4) . ?
C2 C1 1.392(4) . ?
N1 C12 1.397(4) . ?
N1 C1 1.401(4) . ?
N1 C13 1.420(4) . ?
C13 C18 1.397(4) . ?
C13 C14 1.391(4) . ?
C10 C11 1.384(4) . ?
C10 C9 1.402(5) . ?
C14 C15 1.386(5) . ?
C15 C16 1.393(5) . ?
C6 C5 1.392(4) . ?
C6 C1 1.414(4) . ?
C6 C7 1.443(4) . ?
C7 C8 1.396(4) . ?
C7 C12 1.411(4) . ?
C8 C9 1.395(4) . ?
C11 C12 1.395(4) . ?
C3 C4 1.404(5) . ?
C5 C4 1.389(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
C16 C17 C18 122.3(3) . . ?
C16 C17 Br1 119.5(2) . . ?
C18 C17 Br1 118.1(3) . . ?
C3 C2 C1 117.1(3) . . ?
C12 N1 C1 108.3(2) . . ?
C12 N1 C13 124.9(3) . . ?
C1 N1 C13 125.2(3) . . ?
C18 C13 C14 120.5(3) . . ?
C18 C13 N1 119.0(3) . . ?
C14 C13 N1 120.5(3) . . ?
C11 C10 C9 122.3(3) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C15 C16 120.5(3) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 133.4(3) . . ?
C1 C6 C7 106.8(3) . . ?
C2 C1 N1 129.2(3) . . ?
C2 C1 C6 121.9(3) . . ?
N1 C1 C6 108.8(3) . . ?
C8 C7 C12 120.5(3) . . ?
C8 C7 C6 132.3(3) . . ?
C12 C7 C6 107.1(3) . . ?
C9 C8 C7 118.5(3) . . ?
C17 C16 C15 118.4(3) . . ?
C10 C11 C12 117.5(3) . . ?
C11 C12 N1 129.9(3) . . ?
C11 C12 C7 121.1(3) . . ?
N1 C12 C7 108.9(3) . . ?
C2 C3 C4 121.9(3) . . ?
C4 C5 C6 118.9(3) . . ?
C8 C9 C10 120.1(3) . . ?
C17 C18 C13 118.2(3) . . ?
C5 C4 C3 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1573614'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br N'
_chemical_formula_weight         106.94

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

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'
'-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                   14.9529(14)
_cell_length_b                   8.1730(8)
_cell_length_c                   24.260(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2964.9(5)
_cell_formula_units_Z            46
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      21.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2254
_exptl_absorpt_coefficient_mu    15.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker Smart Aepex CCD'
_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            23186
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         28.27
_reflns_number_total             3659
_reflns_number_gt                3370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0267P)²+7.6968P] 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         3659
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_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 0.23186(2) 0.15151(4) 0.320184(12) 0.02141(10) Uani 1 1 d . . .
Br2 Br -0.008765(19) 0.44414(4) 0.170526(13) 0.01863(9) Uani 1 1 d . . .
C2 C 0.2431(2) 0.0892(3) 0.04071(12) 0.0145(5) Uani 1 1 d . . .
H2 H 0.1877 0.0762 0.0594 0.017 Uiso 1 1 calc R . .
N1 N 0.31696(15) 0.2610(3) 0.11402(10) 0.0127(5) Uani 1 1 d . . .
C17 C 0.10332(19) 0.3441(4) 0.18484(12) 0.0139(5) Uani 1 1 d . . .
C12 C 0.40086(18) 0.3354(3) 0.11870(12) 0.0128(5) Uani 1 1 d . . .
C15 C 0.20526(19) 0.2270(4) 0.24849(12) 0.0140(5) Uani 1 1 d . . .
C6 C 0.39402(19) 0.2038(4) 0.03532(12) 0.0143(5) Uani 1 1 d . . .
C3 C 0.2586(2) 0.0163(4) -0.00977(13) 0.0185(6) Uani 1 1 d . . .
H3 H 0.2133 -0.0502 -0.0256 0.022 Uiso 1 1 calc R . .
C13 C 0.24967(19) 0.2684(3) 0.15495(12) 0.0131(5) Uani 1 1 d . . .
C18 C 0.16547(19) 0.3331(3) 0.14275(12) 0.0136(5) Uani 1 1 d . . .
H18 H 0.1513 0.3686 0.1065 0.016 Uiso 1 1 calc R . .
C1 C 0.31203(19) 0.1824(3) 0.06317(12) 0.0127(5) Uani 1 1 d . . .
C5 C 0.4070(2) 0.1322(4) -0.01608(13) 0.0200(6) Uani 1 1 d . . .
H5 H 0.4613 0.1478 -0.0356 0.024 Uiso 1 1 calc R . .
C7 C 0.44996(18) 0.3046(3) 0.07037(12) 0.0131(5) Uani 1 1 d . . .
C14 C 0.26994(18) 0.2143(3) 0.20808(13) 0.0145(6) Uani 1 1 d . . .
H14 H 0.3271 0.1697 0.2163 0.017 Uiso 1 1 calc R . .
C16 C 0.12113(19) 0.2914(3) 0.23799(12) 0.0142(6) Uani 1 1 d . . .
H16 H 0.0773 0.2992 0.2662 0.017 Uiso 1 1 calc R . .
C10 C 0.5190(2) 0.4980(4) 0.15406(13) 0.0164(6) Uani 1 1 d . . .
H10 H 0.5434 0.5655 0.1821 0.020 Uiso 1 1 calc R . .
C4 C 0.3389(2) 0.0374(4) -0.03824(14) 0.0228(7) Uani 1 1 d . . .
H4 H 0.3470 -0.0135 -0.0731 0.027 Uiso 1 1 calc R . .
C8 C 0.5358(2) 0.3701(4) 0.06479(13) 0.0188(6) Uani 1 1 d . . .
H8 H 0.5704 0.3491 0.0327 0.023 Uiso 1 1 calc R . .
C11 C 0.43353(19) 0.4330(3) 0.16095(13) 0.0144(5) Uani 1 1 d . . .
H11 H 0.3992 0.4546 0.1931 0.017 Uiso 1 1 calc R . .
C9 C 0.5693(2) 0.4662(4) 0.10699(14) 0.0214(7) Uani 1 1 d . . .
H9 H 0.6277 0.5112 0.1038 0.026 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01905(16) 0.02737(17) 0.01782(15) 0.00719(12) 0.00069(11) 0.00368(12)
Br2 0.01187(14) 0.01709(15) 0.02692(17) 0.00173(12) -0.00032(11) 0.00504(11)
C2 0.0127(12) 0.0097(12) 0.0210(14) 0.0047(11) -0.0008(11) 0.0001(11)
N1 0.0096(10) 0.0104(11) 0.0183(12) 0.0001(9) 0.0014(9) 0.0002(9)
C17 0.0094(12) 0.0092(12) 0.0230(14) -0.0006(11) -0.0010(11) 0.0019(10)
C12 0.0095(12) 0.0096(12) 0.0193(13) 0.0033(11) -0.0008(10) 0.0005(10)
C15 0.0148(13) 0.0119(13) 0.0151(13) 0.0009(11) -0.0011(10) -0.0003(11)
C6 0.0103(12) 0.0139(13) 0.0187(14) 0.0016(11) -0.0011(11) 0.0012(11)
C3 0.0179(14) 0.0147(14) 0.0230(15) 0.0022(12) -0.0062(12) -0.0035(12)
C13 0.0109(12) 0.0090(12) 0.0193(13) -0.0018(10) 0.0033(11) -0.0024(11)
C18 0.0132(13) 0.0098(12) 0.0178(13) 0.0002(11) -0.0006(11) -0.0014(11)
C1 0.0132(12) 0.0076(12) 0.0173(13) 0.0042(10) 0.0001(10) 0.0019(10)
C5 0.0141(13) 0.0261(16) 0.0199(14) -0.0028(13) 0.0020(11) 0.0005(13)
C7 0.0093(12) 0.0118(13) 0.0183(13) 0.0023(11) 0.0006(10) 0.0020(11)
C14 0.0118(13) 0.0092(12) 0.0227(14) -0.0001(11) -0.0005(11) 0.0014(10)
C16 0.0110(12) 0.0114(13) 0.0202(14) -0.0014(11) 0.0032(10) -0.0025(11)
C10 0.0141(13) 0.0127(13) 0.0223(15) 0.0018(11) -0.0045(11) -0.0014(11)
C4 0.0208(15) 0.0269(17) 0.0206(15) -0.0061(13) -0.0009(12) 0.0001(14)
C8 0.0094(13) 0.0260(16) 0.0209(14) 0.0005(13) 0.0015(11) -0.0006(12)
C11 0.0129(12) 0.0099(13) 0.0203(14) 0.0007(11) 0.0006(11) 0.0016(11)
C9 0.0114(13) 0.0262(17) 0.0267(16) 0.0023(14) -0.0002(12) -0.0062(13)

_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 C15 1.888(3) . ?
Br2 C17 1.897(3) . ?
C2 C3 1.381(4) . ?
C2 C1 1.392(4) . ?
N1 C1 1.393(4) . ?
N1 C12 1.399(4) . ?
N1 C13 1.415(4) . ?
C17 C18 1.384(4) . ?
C17 C16 1.386(4) . ?
C12 C11 1.388(4) . ?
C12 C7 1.406(4) . ?
C15 C14 1.381(4) . ?
C15 C16 1.387(4) . ?
C6 C5 1.391(4) . ?
C6 C1 1.411(4) . ?
C6 C7 1.449(4) . ?
C3 C4 1.395(5) . ?
C13 C14 1.396(4) . ?
C13 C18 1.397(4) . ?
C5 C4 1.387(5) . ?
C7 C8 1.397(4) . ?
C10 C9 1.392(5) . ?
C10 C11 1.394(4) . ?
C8 C9 1.384(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 117.3(3) . . ?
C1 N1 C12 108.7(2) . . ?
C1 N1 C13 127.1(2) . . ?
C12 N1 C13 124.2(2) . . ?
C18 C17 C16 122.5(3) . . ?
C18 C17 Br2 119.1(2) . . ?
C16 C17 Br2 118.3(2) . . ?
C11 C12 N1 128.7(3) . . ?
C11 C12 C7 122.4(3) . . ?
N1 C12 C7 108.8(2) . . ?
C14 C15 C16 122.2(3) . . ?
C14 C15 Br1 118.8(2) . . ?
C16 C15 Br1 119.0(2) . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 133.2(3) . . ?
C1 C6 C7 106.9(3) . . ?
C2 C3 C4 122.0(3) . . ?
C14 C13 C18 120.7(3) . . ?
C14 C13 N1 118.7(3) . . ?
C18 C13 N1 120.6(3) . . ?
C17 C18 C13 118.3(3) . . ?
C2 C1 N1 129.7(3) . . ?
C2 C1 C6 121.6(3) . . ?
N1 C1 C6 108.7(2) . . ?
C4 C5 C6 118.7(3) . . ?
C8 C7 C12 119.4(3) . . ?
C8 C7 C6 133.7(3) . . ?
C12 C7 C6 106.8(2) . . ?
C15 C14 C13 118.7(3) . . ?
C17 C16 C15 117.6(3) . . ?
C9 C10 C11 121.5(3) . . ?
C5 C4 C3 120.6(3) . . ?
C9 C8 C7 118.6(3) . . ?
C12 C11 C10 116.9(3) . . ?
C8 C9 C10 121.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.111
