# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_12mz119_0m
_database_code_depnum_ccdc_archive 'CCDC 1063365'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.858(2)
_cell_length_b                   4.3834(7)
_cell_length_c                   11.1513(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.584(2)
_cell_angle_gamma                90
_cell_volume                     669.81(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3572
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      31.55

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    6.034
_shelx_estimated_absorpt_T_min   0.136
_shelx_estimated_absorpt_T_max   0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5303
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6248
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         31.661
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2091
_reflns_number_gt                1867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0288P)²+0.2747P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0253(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2091
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0551
_refine_ls_wR_factor_gt          0.0539
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42717(3) 0.57961(11) 0.13801(3) 0.01281(8) Uani 0.963(2) 1 d D . P A 1
C1 C 0.34943(13) 0.8147(4) 0.00512(15) 0.0138(3) Uani 0.963(2) 1 d D . P A 1
H1A H 0.3227 0.9997 0.0390 0.017 Uiso 0.963(2) 1 calc R U P A 1
H1B H 0.3923 0.8806 -0.0536 0.017 Uiso 0.963(2) 1 calc R U P A 1
C2 C 0.26752(12) 0.6269(4) -0.05892(14) 0.0100(3) Uani 0.963(2) 1 d D . P A 1
C3 C 0.28133(13) 0.4557(5) -0.16143(16) 0.0125(3) Uani 0.963(2) 1 d D . P A 1
H3 H 0.3432 0.4549 -0.1883 0.015 Uiso 0.963(2) 1 calc R U P A 1
C4 C 0.20481(13) 0.2871(4) -0.22391(15) 0.0136(3) Uani 0.963(2) 1 d D . P A 1
H4 H 0.2144 0.1719 -0.2933 0.016 Uiso 0.963(2) 1 calc R U P A 1
C5 C 0.11370(12) 0.2874(4) -0.18431(14) 0.0119(3) Uani 0.963(2) 1 d D . P A 1
H5 H 0.0610 0.1746 -0.2273 0.014 Uiso 0.963(2) 1 calc R U P A 1
C6 C 0.10050(12) 0.4539(4) -0.08140(14) 0.0103(3) Uani 0.963(2) 1 d D . P A 1
C7 C 0.17683(12) 0.6265(4) -0.01906(14) 0.0103(3) Uani 0.963(2) 1 d D . P A 1
H7 H 0.1670 0.7426 0.0500 0.012 Uiso 0.963(2) 1 calc R U P A 1
N1 N 0.00413(11) 0.4373(3) -0.04965(13) 0.0126(3) Uani 0.963(2) 1 d D . P A 1
Br1B Br 0.4447(8) 0.585(3) 0.1348(10) 0.01281(8) Uani 0.037(2) 1 d D . P A 2
C1B C 0.3869(7) 0.777(5) -0.0208(13) 0.0138(3) Uani 0.037(2) 1 d D . P A 2
H1BA H 0.3803 0.9994 -0.0089 0.017 Uiso 0.037(2) 1 calc R U P A 2
H1BB H 0.4309 0.7452 -0.0819 0.017 Uiso 0.037(2) 1 calc R U P A 2
C2B C 0.2890(7) 0.644(5) -0.0663(11) 0.0100(3) Uani 0.037(2) 1 d D . P A 2
C3B C 0.2774(11) 0.451(8) -0.168(2) 0.0125(3) Uani 0.037(2) 1 d D . P A 2
H3B H 0.3310 0.4142 -0.2100 0.015 Uiso 0.037(2) 1 calc R U P A 2
C4B C 0.1878(13) 0.313(8) -0.207(2) 0.0136(3) Uani 0.037(2) 1 d D . P A 2
H4B H 0.1795 0.1904 -0.2783 0.016 Uiso 0.037(2) 1 calc R U P A 2
C5B C 0.1100(11) 0.357(6) -0.1425(18) 0.0119(3) Uani 0.037(2) 1 d D . P A 2
H5B H 0.0493 0.2586 -0.1677 0.014 Uiso 0.037(2) 1 calc R U P A 2
C6B C 0.1221(8) 0.545(5) -0.0404(15) 0.0103(3) Uani 0.037(2) 1 d D . P A 2
C7B C 0.2102(9) 0.697(5) -0.0045(17) 0.0103(3) Uani 0.037(2) 1 d D . P A 2
H7B H 0.2165 0.8367 0.0615 0.012 Uiso 0.037(2) 1 calc R U P A 2
N1B N 0.0400(9) 0.554(7) 0.0240(17) 0.0126(3) Uani 0.037(2) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9856(17) . ?
C1 C2 1.495(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.394(2) . ?
C2 C3 1.404(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(2) . ?
C6 N1 1.434(2) . ?
C7 H7 0.9500 . ?
N1 N1 1.257(3) 3_565 ?
Br1B C1B 1.986(2) . ?
C1B C2B 1.495(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C7B 1.394(2) . ?
C2B C3B 1.404(2) . ?
C3B C4B 1.391(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.398(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.395(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.398(2) . ?
C6B N1B 1.434(2) . ?
C7B H7B 0.9500 . ?
N1B N1B 1.250(18) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 111.06(11) . . ?
C2 C1 H1A 109.4 . . ?
Br1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Br1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C7 C2 C3 119.84(15) . . ?
C7 C2 C1 120.32(15) . . ?
C3 C2 C1 119.82(15) . . ?
C4 C3 C2 120.35(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.87(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.71(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.65(15) . . ?
C5 C6 N1 114.70(14) . . ?
C7 C6 N1 124.63(15) . . ?
C2 C7 C6 119.56(15) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N1 N1 C6 113.96(18) 3_565 . ?
C2B C1B Br1B 111.05(17) . . ?
C2B C1B H1BA 109.4 . . ?
Br1B C1B H1BA 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
Br1B C1B H1BB 109.4 . . ?
H1BA C1B H1BB 108.0 . . ?
C7B C2B C3B 119.79(19) . . ?
C7B C2B C1B 120.3(2) . . ?
C3B C2B C1B 119.8(2) . . ?
C4B C3B C2B 120.3(2) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 119.9(2) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C6B C5B C4B 119.7(2) . . ?
C6B C5B H5B 120.2 . . ?
C4B C5B H5B 120.2 . . ?
C5B C6B C7B 120.62(19) . . ?
C5B C6B N1B 114.7(2) . . ?
C7B C6B N1B 124.6(2) . . ?
C2B C7B C6B 119.5(2) . . ?
C2B C7B H7B 120.2 . . ?
C6B C7B H7B 120.2 . . ?
N1B N1B C6B 119.6(14) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 89.60(17) . . . . ?
Br1 C1 C2 C3 -91.88(18) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -178.11(17) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
C4 C5 C6 N1 179.93(15) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C1 C2 C7 C6 178.81(14) . . . . ?
C5 C6 C7 C2 -1.3(2) . . . . ?
N1 C6 C7 C2 -179.51(15) . . . . ?
C5 C6 N1 N1 173.23(17) . . . 3_565 ?
C7 C6 N1 N1 -8.4(3) . . . 3_565 ?
Br1B C1B C2B C7B 68.3(17) . . . . ?
Br1B C1B C2B C3B -108(2) . . . . ?
C7B C2B C3B C4B 0(4) . . . . ?
C1B C2B C3B C4B 177(3) . . . . ?
C2B C3B C4B C5B -3(5) . . . . ?
C3B C4B C5B C6B 2(5) . . . . ?
C4B C5B C6B C7B 2(4) . . . . ?
C4B C5B C6B N1B -176(3) . . . . ?
C3B C2B C7B C6B 4(3) . . . . ?
C1B C2B C7B C6B -173.0(16) . . . . ?
C5B C6B C7B C2B -5(3) . . . . ?
N1B C6B C7B C2B 173(3) . . . . ?
C5B C6B N1B N1B -13(5) . . . 3_565 ?
C7B C6B N1B N1B 170(4) . . . 3_565 ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz120_0m
_database_code_depnum_ccdc_archive 'CCDC 1063366'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.8531(19)
_cell_length_b                   4.3928(6)
_cell_length_c                   11.1633(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.597(2)
_cell_angle_gamma                90
_cell_volume                     671.70(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3503
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      31.53

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    6.017
_shelx_estimated_absorpt_T_min   0.137
_shelx_estimated_absorpt_T_max   0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5332
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6638
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         31.628
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2111
_reflns_number_gt                1839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0279P)²+0.2426P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0283(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0553
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42693(4) 0.57960(10) 0.13792(3) 0.01712(8) Uani 0.968(2) 1 d D . P A 1
C1 C 0.34934(13) 0.8140(4) 0.00536(16) 0.0179(3) Uani 0.968(2) 1 d D . P A 1
H1A H 0.3226 0.9987 0.0392 0.022 Uiso 0.968(2) 1 calc R U P A 1
H1B H 0.3922 0.8796 -0.0532 0.022 Uiso 0.968(2) 1 calc R U P A 1
C2 C 0.26727(12) 0.6265(4) -0.05866(14) 0.0136(3) Uani 0.968(2) 1 d D . P A 1
C3 C 0.28092(13) 0.4560(5) -0.16109(16) 0.0162(3) Uani 0.968(2) 1 d D . P A 1
H3 H 0.3428 0.4552 -0.1880 0.019 Uiso 0.968(2) 1 calc R U P A 1
C4 C 0.20425(13) 0.2882(4) -0.22346(16) 0.0181(3) Uani 0.968(2) 1 d D . P A 1
H4 H 0.2137 0.1741 -0.2930 0.022 Uiso 0.968(2) 1 calc R U P A 1
C5 C 0.11363(12) 0.2878(4) -0.18382(15) 0.0158(3) Uani 0.968(2) 1 d D . P A 1
H5 H 0.0610 0.1745 -0.2265 0.019 Uiso 0.968(2) 1 calc R U P A 1
C6 C 0.10043(12) 0.4543(4) -0.08119(14) 0.0130(3) Uani 0.968(2) 1 d D . P A 1
C7 C 0.17681(12) 0.6264(4) -0.01883(14) 0.0133(3) Uani 0.968(2) 1 d D . P A 1
H7 H 0.1670 0.7423 0.0502 0.016 Uiso 0.968(2) 1 calc R U P A 1
N1 N 0.00409(11) 0.4372(3) -0.04925(13) 0.0164(3) Uani 0.968(2) 1 d D . P A 1
Br1B Br 0.4462(9) 0.591(4) 0.1358(11) 0.01712(8) Uani 0.032(2) 1 d D . P A 2
C1B C 0.3869(7) 0.781(5) -0.0189(14) 0.0179(3) Uani 0.032(2) 1 d D . P A 2
H1BA H 0.3793 1.0022 -0.0067 0.022 Uiso 0.032(2) 1 calc R U P A 2
H1BB H 0.4307 0.7519 -0.0804 0.022 Uiso 0.032(2) 1 calc R U P A 2
C2B C 0.2893(7) 0.644(5) -0.0638(12) 0.0136(3) Uani 0.032(2) 1 d D . P A 2
C3B C 0.2784(12) 0.448(8) -0.164(2) 0.0162(3) Uani 0.032(2) 1 d D . P A 2
H3B H 0.3325 0.4092 -0.2053 0.019 Uiso 0.032(2) 1 calc R U P A 2
C4B C 0.1887(13) 0.312(9) -0.205(3) 0.0181(3) Uani 0.032(2) 1 d D . P A 2
H4B H 0.1812 0.1847 -0.2741 0.022 Uiso 0.032(2) 1 calc R U P A 2
C5B C 0.1101(11) 0.362(6) -0.1426(18) 0.0158(3) Uani 0.032(2) 1 d D . P A 2
H5B H 0.0485 0.2723 -0.1705 0.019 Uiso 0.032(2) 1 calc R U P A 2
C6B C 0.1222(9) 0.545(5) -0.0395(16) 0.0130(3) Uani 0.032(2) 1 d D . P A 2
C7B C 0.2105(9) 0.696(6) -0.0025(19) 0.0133(3) Uani 0.032(2) 1 d D . P A 2
H7B H 0.2167 0.8337 0.0640 0.016 Uiso 0.032(2) 1 calc R U P A 2
N1B N 0.0392(10) 0.558(8) 0.023(2) 0.0164(3) Uani 0.032(2) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9824(17) . ?
C1 C2 1.496(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.391(2) . ?
C2 C3 1.403(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(2) . ?
C6 N1 1.434(2) . ?
C7 H7 0.9500 . ?
N1 N1 1.250(3) 3_565 ?
Br1B C1B 1.982(2) . ?
C1B C2B 1.496(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C7B 1.391(2) . ?
C2B C3B 1.403(2) . ?
C3B C4B 1.391(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.392(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.394(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.398(2) . ?
C6B N1B 1.434(2) . ?
C7B H7B 0.9500 . ?
N1B N1B 1.241(18) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 111.04(11) . . ?
C2 C1 H1A 109.4 . . ?
Br1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Br1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C7 C2 C3 119.86(15) . . ?
C7 C2 C1 120.27(15) . . ?
C3 C2 C1 119.85(16) . . ?
C4 C3 C2 120.32(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.94(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.72(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.68(15) . . ?
C5 C6 N1 114.72(14) . . ?
C7 C6 N1 124.58(15) . . ?
C2 C7 C6 119.47(15) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N1 N1 C6 113.94(18) 3_565 . ?
C2B C1B Br1B 111.03(18) . . ?
C2B C1B H1BA 109.4 . . ?
Br1B C1B H1BA 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
Br1B C1B H1BB 109.4 . . ?
H1BA C1B H1BB 108.0 . . ?
C7B C2B C3B 119.82(19) . . ?
C7B C2B C1B 120.2(2) . . ?
C3B C2B C1B 119.8(2) . . ?
C4B C3B C2B 120.3(2) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 119.9(2) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B C6B 119.7(2) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C5B C6B C7B 120.6(2) . . ?
C5B C6B N1B 114.8(2) . . ?
C7B C6B N1B 124.6(2) . . ?
C2B C7B C6B 119.4(2) . . ?
C2B C7B H7B 120.3 . . ?
C6B C7B H7B 120.3 . . ?
N1B N1B C6B 119.8(15) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 89.58(17) . . . . ?
Br1 C1 C2 C3 -92.00(18) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -178.05(17) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C4 C5 C6 N1 179.85(15) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C1 C2 C7 C6 178.79(14) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
N1 C6 C7 C2 -179.69(15) . . . . ?
C5 C6 N1 N1 173.37(18) . . . 3_565 ?
C7 C6 N1 N1 -8.0(3) . . . 3_565 ?
Br1B C1B C2B C7B 69.2(19) . . . . ?
Br1B C1B C2B C3B -107(2) . . . . ?
C7B C2B C3B C4B 1(5) . . . . ?
C1B C2B C3B C4B 178(3) . . . . ?
C2B C3B C4B C5B -2(6) . . . . ?
C3B C4B C5B C6B -1(5) . . . . ?
C4B C5B C6B C7B 5(4) . . . . ?
C4B C5B C6B N1B -174(3) . . . . ?
C3B C2B C7B C6B 2(3) . . . . ?
C1B C2B C7B C6B -174.4(18) . . . . ?
C5B C6B C7B C2B -5(3) . . . . ?
N1B C6B C7B C2B 174(3) . . . . ?
C5B C6B N1B N1B -8(6) . . . 3_565 ?
C7B C6B N1B N1B 173(4) . . . 3_565 ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz121_0m
_database_code_depnum_ccdc_archive 'CCDC 1063367'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.891(2)
_cell_length_b                   4.4024(7)
_cell_length_c                   11.1676(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.719(2)
_cell_angle_gamma                90
_cell_volume                     675.03(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3022
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      31.51

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.987
_shelx_estimated_absorpt_T_min   0.137
_shelx_estimated_absorpt_T_max   0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4237
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6512
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.967
_diffrn_reflns_theta_max         31.629
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2119
_reflns_number_gt                1794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0340P)²+0.1531P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42627(4) 0.58035(15) 0.13805(5) 0.02278(10) Uani 0.930(3) 1 d D . P A
1
C1 C 0.34848(16) 0.8138(4) 0.00550(19) 0.0232(4) Uani 0.930(3) 1 d D . P A 1
H1A H 0.3219 0.9981 0.0393 0.028 Uiso 0.930(3) 1 calc R U P A 1
H1B H 0.3910 0.8790 -0.0533 0.028 Uiso 0.930(3) 1 calc R U P A 1
C2 C 0.26673(14) 0.6268(4) -0.05803(16) 0.0172(3) Uani 0.930(3) 1 d D . P A 1
C3 C 0.28026(15) 0.4566(7) -0.1604(2) 0.0213(4) Uani 0.930(3) 1 d D . P A 1
H3 H 0.3420 0.4553 -0.1871 0.026 Uiso 0.930(3) 1 calc R U P A 1
C4 C 0.20371(16) 0.2898(5) -0.22294(18) 0.0225(4) Uani 0.930(3) 1 d D . P A 1
H4 H 0.2131 0.1762 -0.2926 0.027 Uiso 0.930(3) 1 calc R U P A 1
C5 C 0.11306(14) 0.2894(5) -0.18335(17) 0.0206(4) Uani 0.930(3) 1 d D . P A 1
H5 H 0.0605 0.1766 -0.2261 0.025 Uiso 0.930(3) 1 calc R U P A 1
C6 C 0.10027(13) 0.4552(4) -0.08081(16) 0.0171(4) Uani 0.930(3) 1 d D . P A 1
C7 C 0.17653(14) 0.6264(4) -0.01847(16) 0.0173(4) Uani 0.930(3) 1 d D . P A 1
H7 H 0.1668 0.7418 0.0506 0.021 Uiso 0.930(3) 1 calc R U P A 1
N1 N 0.00394(12) 0.4379(4) -0.04911(14) 0.0214(4) Uani 0.930(3) 1 d D . P A 1
Br1B Br 0.4434(6) 0.595(2) 0.1346(7) 0.02278(10) Uani 0.070(3) 1 d D . P A 2
C1B C 0.3845(6) 0.784(4) -0.0204(11) 0.0232(4) Uani 0.070(3) 1 d D . P A 2
H1BA H 0.3773 1.0051 -0.0085 0.028 Uiso 0.070(3) 1 calc R U P A 2
H1BB H 0.4282 0.7538 -0.0817 0.028 Uiso 0.070(3) 1 calc R U P A 2
C2B C 0.2873(5) 0.648(4) -0.0653(9) 0.0172(3) Uani 0.070(3) 1 d D . P A 2
C3B C 0.2760(10) 0.457(7) -0.1670(19) 0.0213(4) Uani 0.070(3) 1 d D . P A 2
H3B H 0.3282 0.4327 -0.2121 0.026 Uiso 0.070(3) 1 calc R U P A 2
C4B C 0.1888(11) 0.304(6) -0.202(2) 0.0225(4) Uani 0.070(3) 1 d D . P A 2
H4B H 0.1828 0.1657 -0.2681 0.027 Uiso 0.070(3) 1 calc R U P A 2
C5B C 0.1100(9) 0.354(4) -0.1404(14) 0.0206(4) Uani 0.070(3) 1 d D . P A 2
H5B H 0.0488 0.2613 -0.1676 0.025 Uiso 0.070(3) 1 calc R U P A 2
C6B C 0.1218(7) 0.540(4) -0.0386(13) 0.0171(4) Uani 0.070(3) 1 d D . P A 2
C7B C 0.2100(7) 0.689(4) -0.0010(14) 0.0173(4) Uani 0.070(3) 1 d D . P A 2
H7B H 0.2171 0.8182 0.0680 0.021 Uiso 0.070(3) 1 calc R U P A 2
N1B N 0.0380(7) 0.559(5) 0.0223(13) 0.0214(4) Uani 0.070(3) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9823(19) . ?
C1 C2 1.492(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.390(3) . ?
C2 C3 1.403(2) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C6 N1 1.437(2) . ?
C7 H7 0.9500 . ?
N1 N1 1.245(3) 3_565 ?
Br1B C1B 1.982(2) . ?
C1B C2B 1.492(3) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C7B 1.390(3) . ?
C2B C3B 1.403(3) . ?
C3B C4B 1.390(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.397(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.392(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.397(3) . ?
C6B N1B 1.437(3) . ?
C7B H7B 0.9500 . ?
N1B N1B 1.211(16) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 111.01(13) . . ?
C2 C1 H1A 109.4 . . ?
Br1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Br1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C7 C2 C3 119.78(17) . . ?
C7 C2 C1 120.48(18) . . ?
C3 C2 C1 119.72(18) . . ?
C4 C3 C2 120.32(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.96(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.57(17) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.75(16) . . ?
C5 C6 N1 114.49(16) . . ?
C7 C6 N1 124.74(17) . . ?
C2 C7 C6 119.62(17) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N1 N1 C6 113.8(2) 3_565 . ?
C2B C1B Br1B 110.98(18) . . ?
C2B C1B H1BA 109.4 . . ?
Br1B C1B H1BA 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
Br1B C1B H1BB 109.4 . . ?
H1BA C1B H1BB 108.0 . . ?
C7B C2B C3B 119.7(2) . . ?
C7B C2B C1B 120.4(2) . . ?
C3B C2B C1B 119.7(2) . . ?
C4B C3B C2B 120.3(2) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 119.9(2) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 119.5(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C7B 120.8(2) . . ?
C5B C6B N1B 114.5(2) . . ?
C7B C6B N1B 124.7(2) . . ?
C2B C7B C6B 119.6(2) . . ?
C2B C7B H7B 120.2 . . ?
C6B C7B H7B 120.2 . . ?
N1B N1B C6B 120.0(12) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 89.69(19) . . . . ?
Br1 C1 C2 C3 -92.0(2) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C4 C5 C6 N1 179.86(18) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 178.56(16) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
N1 C6 C7 C2 -179.66(17) . . . . ?
C5 C6 N1 N1 173.3(2) . . . 3_565 ?
C7 C6 N1 N1 -8.1(3) . . . 3_565 ?
Br1B C1B C2B C7B 65.9(14) . . . . ?
Br1B C1B C2B C3B -108.6(19) . . . . ?
C7B C2B C3B C4B -1(4) . . . . ?
C1B C2B C3B C4B 173(2) . . . . ?
C2B C3B C4B C5B 4(4) . . . . ?
C3B C4B C5B C6B -5(4) . . . . ?
C4B C5B C6B C7B 3(3) . . . . ?
C4B C5B C6B N1B -176(2) . . . . ?
C3B C2B C7B C6B 0(3) . . . . ?
C1B C2B C7B C6B -174.7(15) . . . . ?
C5B C6B C7B C2B -1(3) . . . . ?
N1B C6B C7B C2B 178.2(19) . . . . ?
C5B C6B N1B N1B -7(4) . . . 3_565 ?
C7B C6B N1B N1B 174(3) . . . 3_565 ?

_refine_diff_density_max         0.766
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz122_0m
_database_code_depnum_ccdc_archive 'CCDC 1063368'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.936(2)
_cell_length_b                   4.4112(7)
_cell_length_c                   11.1717(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.840(2)
_cell_angle_gamma                90
_cell_volume                     678.62(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2585
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      31.47

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.956
_shelx_estimated_absorpt_T_min   0.138
_shelx_estimated_absorpt_T_max   0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4931
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6570
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.958
_diffrn_reflns_theta_max         31.613
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2135
_reflns_number_gt                1746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0316P)²+0.1601P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2135
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42552(5) 0.5810(2) 0.13822(7) 0.02915(12) Uani 0.884(3) 1 d D . P A 1
C1 C 0.34782(19) 0.8137(5) 0.0055(2) 0.0289(5) Uani 0.884(3) 1 d D . P A 1
H1A H 0.3216 0.9984 0.0391 0.035 Uiso 0.884(3) 1 calc R U P A 1
H1B H 0.3900 0.8776 -0.0535 0.035 Uiso 0.884(3) 1 calc R U P A 1
C2 C 0.26606(16) 0.6268(5) -0.05724(18) 0.0219(4) Uani 0.884(3) 1 d D . P A 1
C3 C 0.27895(19) 0.4575(10) -0.1598(3) 0.0258(4) Uani 0.884(3) 1 d D . P A 1
H3 H 0.3403 0.4568 -0.1868 0.031 Uiso 0.884(3) 1 calc R U P A 1
C4 C 0.20268(19) 0.2909(8) -0.2222(3) 0.0287(5) Uani 0.884(3) 1 d D . P A 1
H4 H 0.2118 0.1772 -0.2918 0.034 Uiso 0.884(3) 1 calc R U P A 1
C5 C 0.11275(15) 0.2913(6) -0.1822(2) 0.0252(5) Uani 0.884(3) 1 d D . P A 1
H5 H 0.0601 0.1790 -0.2249 0.030 Uiso 0.884(3) 1 calc R U P A 1
C6 C 0.10027(15) 0.4565(5) -0.07979(19) 0.0215(4) Uani 0.884(3) 1 d D . P A 1
C7 C 0.17640(17) 0.6270(5) -0.01814(18) 0.0218(4) Uani 0.884(3) 1 d D . P A 1
H7 H 0.1668 0.7432 0.0506 0.026 Uiso 0.884(3) 1 calc R U P A 1
N1 N 0.00403(14) 0.4388(5) -0.04902(16) 0.0279(4) Uani 0.884(3) 1 d D . P A 1
Br1B Br 0.4418(4) 0.5975(19) 0.1339(6) 0.02915(12) Uani 0.116(3) 1 d D . P A 2
C1B C 0.3828(6) 0.787(3) -0.0210(9) 0.0289(5) Uani 0.116(3) 1 d D . P A 2
H1BA H 0.3754 1.0078 -0.0089 0.035 Uiso 0.116(3) 1 calc R U P A 2
H1BB H 0.4262 0.7579 -0.0823 0.035 Uiso 0.116(3) 1 calc R U P A 2
C2B C 0.2859(5) 0.651(3) -0.0656(7) 0.0219(4) Uani 0.116(3) 1 d D . P A 2
C3B C 0.2749(10) 0.460(7) -0.167(2) 0.0258(4) Uani 0.116(3) 1 d D . P A 2
H3B H 0.3277 0.4307 -0.2104 0.031 Uiso 0.116(3) 1 calc R U P A 2
C4B C 0.1873(10) 0.313(6) -0.2048(18) 0.0287(5) Uani 0.116(3) 1 d D . P A 2
H4B H 0.1804 0.1828 -0.2734 0.034 Uiso 0.116(3) 1 calc R U P A 2
C5B C 0.1096(7) 0.357(4) -0.1417(11) 0.0252(5) Uani 0.116(3) 1 d D . P A 2
H5B H 0.0487 0.2649 -0.1691 0.030 Uiso 0.116(3) 1 calc R U P A 2
C6B C 0.1218(6) 0.538(3) -0.0385(10) 0.0215(4) Uani 0.116(3) 1 d D . P A 2
C7B C 0.2096(6) 0.685(3) -0.0007(11) 0.0218(4) Uani 0.116(3) 1 d D . P A 2
H7B H 0.2171 0.8095 0.0697 0.026 Uiso 0.116(3) 1 calc R U P A 2
N1B N 0.0371(5) 0.559(3) 0.0199(10) 0.0279(4) Uani 0.116(3) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.983(2) . ?
C1 C2 1.491(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.386(3) . ?
C2 C3 1.402(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 N1 1.437(3) . ?
C7 H7 0.9500 . ?
N1 N1 1.242(4) 3_565 ?
Br1B C1B 1.983(2) . ?
C1B C2B 1.492(3) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C7B 1.386(3) . ?
C2B C3B 1.402(3) . ?
C3B C4B 1.389(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.394(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.390(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.393(3) . ?
C6B N1B 1.437(3) . ?
C7B H7B 0.9500 . ?
N1B N1B 1.181(14) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.81(14) . . ?
C2 C1 H1A 109.5 . . ?
Br1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
Br1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 119.53(19) . . ?
C7 C2 C1 120.8(2) . . ?
C3 C2 C1 119.6(2) . . ?
C4 C3 C2 120.53(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.67(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.80(19) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.53(18) . . ?
C5 C6 N1 114.08(19) . . ?
C7 C6 N1 125.4(2) . . ?
C2 C7 C6 119.93(19) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 N1 C6 113.7(2) 3_565 . ?
C2B C1B Br1B 110.76(19) . . ?
C2B C1B H1BA 109.5 . . ?
Br1B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
Br1B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 108.1 . . ?
C7B C2B C3B 119.4(2) . . ?
C7B C2B C1B 120.6(3) . . ?
C3B C2B C1B 119.6(3) . . ?
C4B C3B C2B 120.6(2) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C5B 119.7(2) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C6B C5B C4B 119.7(2) . . ?
C6B C5B H5B 120.1 . . ?
C4B C5B H5B 120.1 . . ?
C5B C6B C7B 120.6(2) . . ?
C5B C6B N1B 114.2(2) . . ?
C7B C6B N1B 125.2(2) . . ?
C2B C7B C6B 120.0(2) . . ?
C2B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
N1B N1B C6B 122.1(10) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 89.9(2) . . . . ?
Br1 C1 C2 C3 -92.5(3) . . . . ?
C7 C2 C3 C4 0.0(6) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C4 C5 C6 N1 179.6(2) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
C1 C2 C7 C6 178.45(19) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
N1 C6 C7 C2 -179.6(2) . . . . ?
C5 C6 N1 N1 173.2(2) . . . 3_565 ?
C7 C6 N1 N1 -8.7(4) . . . 3_565 ?
Br1B C1B C2B C7B 64.8(11) . . . . ?
Br1B C1B C2B C3B -108.4(19) . . . . ?
C7B C2B C3B C4B 2(4) . . . . ?
C1B C2B C3B C4B 175(2) . . . . ?
C2B C3B C4B C5B 0(5) . . . . ?
C3B C4B C5B C6B -3(4) . . . . ?
C4B C5B C6B C7B 3(3) . . . . ?
C4B C5B C6B N1B -178(2) . . . . ?
C3B C2B C7B C6B -2(2) . . . . ?
C1B C2B C7B C6B -175.1(12) . . . . ?
C5B C6B C7B C2B 0(3) . . . . ?
N1B C6B C7B C2B -179.0(14) . . . . ?
C5B C6B N1B N1B -3(3) . . . 3_565 ?
C7B C6B N1B N1B 176(2) . . . 3_565 ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz123_0m
_database_code_depnum_ccdc_archive 'CCDC 1063369'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.9822(18)
_cell_length_b                   4.4209(6)
_cell_length_c                   11.1785(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.951(2)
_cell_angle_gamma                90
_cell_volume                     682.57(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    2475
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      29.74

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.921
_shelx_estimated_absorpt_T_min   0.139
_shelx_estimated_absorpt_T_max   0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4779
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      210(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7202
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         31.657
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2155
_reflns_number_gt                1679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0361P)²+0.1153P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.036(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2155
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42495(8) 0.5810(3) 0.13838(11) 0.03604(17) Uani 0.834(4) 1 d D . P A 1
C1 C 0.3472(2) 0.8137(6) 0.0059(2) 0.0342(6) Uani 0.834(4) 1 d D . P A 1
H1A H 0.3214 0.9959 0.0393 0.041 Uiso 0.834(4) 1 calc R U P A 1
H1B H 0.3887 0.8771 -0.0525 0.041 Uiso 0.834(4) 1 calc R U P A 1
C2 C 0.26550(17) 0.6262(6) -0.0568(2) 0.0259(5) Uani 0.834(4) 1 d D . P A 1
C3 C 0.2782(2) 0.4584(14) -0.1592(4) 0.0307(5) Uani 0.834(4) 1 d D . P A 1
H3 H 0.3386 0.4577 -0.1859 0.037 Uiso 0.834(4) 1 calc R U P A 1
C4 C 0.2019(2) 0.2927(11) -0.2215(3) 0.0349(5) Uani 0.834(4) 1 d D . P A 1
H4 H 0.2107 0.1809 -0.2905 0.042 Uiso 0.834(4) 1 calc R U P A 1
C5 C 0.11229(17) 0.2927(6) -0.1816(2) 0.0301(5) Uani 0.834(4) 1 d D . P A 1
H5 H 0.0603 0.1817 -0.2236 0.036 Uiso 0.834(4) 1 calc R U P A 1
C6 C 0.10043(16) 0.4575(6) -0.0794(2) 0.0260(5) Uani 0.834(4) 1 d D . P A 1
C7 C 0.17596(18) 0.6268(6) -0.0175(2) 0.0252(5) Uani 0.834(4) 1 d D . P A 1
H7 H 0.1666 0.7412 0.0506 0.030 Uiso 0.834(4) 1 calc R U P A 1
N1 N 0.00386(16) 0.4388(5) -0.04866(19) 0.0337(5) Uani 0.834(4) 1 d D . P A 1
Br1B Br 0.4389(4) 0.6015(19) 0.1337(6) 0.03604(17) Uani 0.166(4) 1 d D . P A 2
C1B C 0.3806(5) 0.789(3) -0.0219(8) 0.0342(6) Uani 0.166(4) 1 d D . P A 2
H1BA H 0.3732 1.0066 -0.0105 0.041 Uiso 0.166(4) 1 calc R U P A 2
H1BB H 0.4236 0.7585 -0.0822 0.041 Uiso 0.166(4) 1 calc R U P A 2
C2B C 0.2839(4) 0.651(3) -0.0668(7) 0.0259(5) Uani 0.166(4) 1 d D . P A 2
C3B C 0.2734(9) 0.458(6) -0.1670(19) 0.0307(5) Uani 0.166(4) 1 d D . P A 2
H3B H 0.3255 0.4288 -0.2095 0.037 Uiso 0.166(4) 1 calc R U P A 2
C4B C 0.1863(9) 0.310(6) -0.2041(17) 0.0349(5) Uani 0.166(4) 1 d D . P A 2
H4B H 0.1796 0.1798 -0.2714 0.042 Uiso 0.166(4) 1 calc R U P A 2
C5B C 0.1087(6) 0.354(3) -0.1413(9) 0.0301(5) Uani 0.166(4) 1 d D . P A 2
H5B H 0.0489 0.2599 -0.1677 0.036 Uiso 0.166(4) 1 calc R U P A 2
C6B C 0.1207(5) 0.537(2) -0.0396(8) 0.0260(5) Uani 0.166(4) 1 d D . P A 2
C7B C 0.2081(6) 0.682(3) -0.0007(8) 0.0252(5) Uani 0.166(4) 1 d D . P A 2
H7B H 0.2159 0.8011 0.0699 0.030 Uiso 0.166(4) 1 calc R U P A 2
N1B N 0.0362(5) 0.555(3) 0.0202(8) 0.0337(5) Uani 0.166(4) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.983(2) . ?
C1 C2 1.495(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C7 1.390(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.388(3) . ?
C6 N1 1.447(3) . ?
C7 H7 0.9400 . ?
N1 N1 1.235(4) 3_565 ?
Br1B C1B 1.983(3) . ?
C1B C2B 1.495(3) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C2B C7B 1.390(3) . ?
C2B C3B 1.398(3) . ?
C3B C4B 1.389(3) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.394(4) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.386(4) . ?
C5B H5B 0.9400 . ?
C6B C7B 1.388(3) . ?
C6B N1B 1.446(3) . ?
C7B H7B 0.9400 . ?
N1B N1B 1.149(13) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.67(15) . . ?
C2 C1 H1A 109.5 . . ?
Br1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
Br1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 119.6(2) . . ?
C7 C2 C1 120.7(2) . . ?
C3 C2 C1 119.6(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 N1 113.7(2) . . ?
C7 C6 N1 125.3(2) . . ?
C6 C7 C2 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
N1 N1 C6 113.4(3) 3_565 . ?
C2B C1B Br1B 110.60(19) . . ?
C2B C1B H1BA 109.5 . . ?
Br1B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
Br1B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 108.1 . . ?
C7B C2B C3B 119.5(2) . . ?
C7B C2B C1B 120.4(3) . . ?
C3B C2B C1B 119.6(3) . . ?
C4B C3B C2B 120.4(2) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 119.9(2) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C6B C5B C4B 119.4(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C7B 121.0(2) . . ?
C5B C6B N1B 114.0(3) . . ?
C7B C6B N1B 125.0(3) . . ?
C6B C7B C2B 119.6(2) . . ?
C6B C7B H7B 120.2 . . ?
C2B C7B H7B 120.2 . . ?
N1B N1B C6B 122.0(9) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 90.1(3) . . . . ?
Br1 C1 C2 C3 -92.6(4) . . . . ?
C7 C2 C3 C4 0.0(7) . . . . ?
C1 C2 C3 C4 -177.4(5) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C4 C5 C6 N1 179.7(3) . . . . ?
C5 C6 C7 C2 -1.4(4) . . . . ?
N1 C6 C7 C2 -179.8(2) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C1 C2 C7 C6 178.2(2) . . . . ?
C5 C6 N1 N1 173.3(3) . . . 3_565 ?
C7 C6 N1 N1 -8.2(4) . . . 3_565 ?
Br1B C1B C2B C7B 63.6(10) . . . . ?
Br1B C1B C2B C3B -108.1(18) . . . . ?
C7B C2B C3B C4B 3(4) . . . . ?
C1B C2B C3B C4B 175(2) . . . . ?
C2B C3B C4B C5B 0(4) . . . . ?
C3B C4B C5B C6B -2(4) . . . . ?
C4B C5B C6B C7B 1(3) . . . . ?
C4B C5B C6B N1B -177.6(18) . . . . ?
C5B C6B C7B C2B 2(2) . . . . ?
N1B C6B C7B C2B -179.3(11) . . . . ?
C3B C2B C7B C6B -4(2) . . . . ?
C1B C2B C7B C6B -175.8(10) . . . . ?
C5B C6B N1B N1B -6(2) . . . 3_565 ?
C7B C6B N1B N1B 174.9(18) . . . 3_565 ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz124_0m
_database_code_depnum_ccdc_archive 'CCDC 1063370'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   14.0179(18)
_cell_length_b                   4.4297(6)
_cell_length_c                   11.1892(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.047(2)
_cell_angle_gamma                90
_cell_volume                     686.15(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2180
_cell_measurement_theta_min      2.533
_cell_measurement_theta_max      28.68

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.890
_shelx_estimated_absorpt_T_min   0.140
_shelx_estimated_absorpt_T_max   0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4461
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7107
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         31.698
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2174
_reflns_number_gt                1588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0394P)²+0.0281P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2174
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.036
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42481(12) 0.5774(4) 0.13779(15) 0.0432(2) Uani 0.782(4) 1 d D . P A 1
C1 C 0.3463(2) 0.8136(6) 0.0064(3) 0.0387(7) Uani 0.782(4) 1 d D . P A 1
H1A H 0.3204 0.9940 0.0406 0.046 Uiso 0.782(4) 1 calc R U P A 1
H1B H 0.3871 0.8789 -0.0522 0.046 Uiso 0.782(4) 1 calc R U P A 1
C2 C 0.26488(18) 0.6245(7) -0.0559(2) 0.0300(5) Uani 0.782(4) 1 d D . P A 1
C3 C 0.2774(3) 0.4592(18) -0.1583(5) 0.0358(5) Uani 0.782(4) 1 d D . P A 1
H3 H 0.3378 0.4595 -0.1849 0.043 Uiso 0.782(4) 1 calc R U P A 1
C4 C 0.2013(3) 0.2939(14) -0.2214(4) 0.0415(6) Uani 0.782(4) 1 d D . P A 1
H4 H 0.2101 0.1834 -0.2906 0.050 Uiso 0.782(4) 1 calc R U P A 1
C5 C 0.11170(18) 0.2931(7) -0.1814(3) 0.0340(6) Uani 0.782(4) 1 d D . P A 1
H5 H 0.0598 0.1821 -0.2234 0.041 Uiso 0.782(4) 1 calc R U P A 1
C6 C 0.10003(18) 0.4586(6) -0.0786(3) 0.0305(6) Uani 0.782(4) 1 d D . P A 1
C7 C 0.1754(2) 0.6270(6) -0.0174(2) 0.0288(5) Uani 0.782(4) 1 d D . P A 1
H7 H 0.1661 0.7429 0.0501 0.035 Uiso 0.782(4) 1 calc R U P A 1
N1 N 0.00394(17) 0.4389(6) -0.0486(2) 0.0390(6) Uani 0.782(4) 1 d D . P A 1
Br1B Br 0.4353(5) 0.6161(15) 0.1368(6) 0.0432(2) Uani 0.218(4) 1 d D . P A 2
C1B C 0.3787(5) 0.793(2) -0.0221(7) 0.0387(7) Uani 0.218(4) 1 d D . P A 2
H1BA H 0.3708 1.0111 -0.0135 0.046 Uiso 0.218(4) 1 calc R U P A 2
H1BB H 0.4225 0.7584 -0.0810 0.046 Uiso 0.218(4) 1 calc R U P A 2
C2B C 0.2828(4) 0.651(2) -0.0664(6) 0.0300(5) Uani 0.218(4) 1 d D . P A 2
C3B C 0.2731(8) 0.457(6) -0.1656(19) 0.0358(5) Uani 0.218(4) 1 d D . P A 2
H3B H 0.3255 0.4271 -0.2074 0.043 Uiso 0.218(4) 1 calc R U P A 2
C4B C 0.1863(8) 0.307(5) -0.2033(17) 0.0415(6) Uani 0.218(4) 1 d D . P A 2
H4B H 0.1804 0.1744 -0.2698 0.050 Uiso 0.218(4) 1 calc R U P A 2
C5B C 0.1081(5) 0.353(2) -0.1418(8) 0.0340(6) Uani 0.218(4) 1 d D . P A 2
H5B H 0.0482 0.2611 -0.1690 0.041 Uiso 0.218(4) 1 calc R U P A 2
C6B C 0.1201(5) 0.538(2) -0.0395(7) 0.0305(6) Uani 0.218(4) 1 d D . P A 2
C7B C 0.2072(5) 0.680(2) -0.0005(7) 0.0288(5) Uani 0.218(4) 1 d D . P A 2
H7B H 0.2153 0.7967 0.0706 0.035 Uiso 0.218(4) 1 calc R U P A 2
N1B N 0.0353(4) 0.557(2) 0.0181(7) 0.0390(6) Uani 0.218(4) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.989(2) . ?
C1 C2 1.497(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C7 1.388(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.398(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.384(4) . ?
C6 N1 1.441(3) . ?
C7 H7 0.9400 . ?
N1 N1 1.236(5) 3_565 ?
Br1B C1B 1.989(3) . ?
C1B C2B 1.497(3) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C2B C7B 1.388(3) . ?
C2B C3B 1.394(3) . ?
C3B C4B 1.392(3) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.398(4) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.395(4) . ?
C5B H5B 0.9400 . ?
C6B C7B 1.383(4) . ?
C6B N1B 1.440(3) . ?
C7B H7B 0.9400 . ?
N1B N1B 1.131(12) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.03(16) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 C1 120.7(2) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 N1 126.0(2) . . ?
C5 C6 N1 113.3(2) . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N1 N1 C6 113.2(3) 3_565 . ?
C2B C1B Br1B 109.99(19) . . ?
C2B C1B H1BA 109.7 . . ?
Br1B C1B H1BA 109.7 . . ?
C2B C1B H1BB 109.7 . . ?
Br1B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?
C7B C2B C3B 119.6(2) . . ?
C7B C2B C1B 120.4(3) . . ?
C3B C2B C1B 119.5(3) . . ?
C4B C3B C2B 120.5(2) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C5B 119.7(2) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C6B C5B C4B 119.2(2) . . ?
C6B C5B H5B 120.4 . . ?
C4B C5B H5B 120.4 . . ?
C7B C6B C5B 120.8(2) . . ?
C7B C6B N1B 125.5(3) . . ?
C5B C6B N1B 113.7(3) . . ?
C6B C7B C2B 120.0(2) . . ?
C6B C7B H7B 120.0 . . ?
C2B C7B H7B 120.0 . . ?
N1B N1B C6B 123.4(8) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 91.6(3) . . . . ?
Br1 C1 C2 C3 -92.5(5) . . . . ?
C7 C2 C3 C4 -0.7(10) . . . . ?
C1 C2 C3 C4 -176.7(6) . . . . ?
C2 C3 C4 C5 -0.2(11) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C4 C5 C6 N1 179.5(4) . . . . ?
C5 C6 C7 C2 -2.1(4) . . . . ?
N1 C6 C7 C2 179.7(3) . . . . ?
C3 C2 C7 C6 1.9(6) . . . . ?
C1 C2 C7 C6 177.8(2) . . . . ?
C7 C6 N1 N1 -8.3(5) . . . 3_565 ?
C5 C6 N1 N1 173.4(3) . . . 3_565 ?
Br1B C1B C2B C7B 62.0(9) . . . . ?
Br1B C1B C2B C3B -109.7(17) . . . . ?
C7B C2B C3B C4B 4(4) . . . . ?
C1B C2B C3B C4B 176(2) . . . . ?
C2B C3B C4B C5B 1(4) . . . . ?
C3B C4B C5B C6B -3(3) . . . . ?
C4B C5B C6B C7B 2(2) . . . . ?
C4B C5B C6B N1B -177.7(17) . . . . ?
C5B C6B C7B C2B 2.8(18) . . . . ?
N1B C6B C7B C2B -177.9(10) . . . . ?
C3B C2B C7B C6B -6(2) . . . . ?
C1B C2B C7B C6B -177.3(8) . . . . ?
C7B C6B N1B N1B 178.3(15) . . . 3_565 ?
C5B C6B N1B N1B -2(2) . . . 3_565 ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz125_0m
_database_code_depnum_ccdc_archive 'CCDC 1063371'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   14.051(2)
_cell_length_b                   4.4406(6)
_cell_length_c                   11.2041(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.129(2)
_cell_angle_gamma                90
_cell_volume                     690.24(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.65

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.855
_shelx_estimated_absorpt_T_min   0.141
_shelx_estimated_absorpt_T_max   0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4237
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      270(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7672
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         31.671
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2197
_reflns_number_gt                1541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0382P)²+0.1364P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42463(16) 0.5754(4) 0.13745(19) 0.0501(2) Uani 0.741(4) 1 d D . P A 1
C1 C 0.3457(2) 0.8129(7) 0.0076(3) 0.0429(8) Uani 0.741(4) 1 d D . P A 1
H1A H 0.3202 0.9900 0.0422 0.052 Uiso 0.741(4) 1 calc R U P A 1
H1B H 0.3856 0.8793 -0.0504 0.052 Uiso 0.741(4) 1 calc R U P A 1
C2 C 0.26396(19) 0.6240(8) -0.0552(3) 0.0348(5) Uani 0.741(4) 1 d D . P A 1
C3 C 0.2766(3) 0.463(2) -0.1582(7) 0.0409(5) Uani 0.741(4) 1 d D . P A 1
H3 H 0.3360 0.4659 -0.1849 0.049 Uiso 0.741(4) 1 calc R U P A 1
C4 C 0.2006(3) 0.2981(16) -0.2212(5) 0.0463(7) Uani 0.741(4) 1 d D . P A 1
H4 H 0.2091 0.1906 -0.2899 0.056 Uiso 0.741(4) 1 calc R U P A 1
C5 C 0.1117(2) 0.2945(8) -0.1811(3) 0.0391(7) Uani 0.741(4) 1 d D . P A 1
H5 H 0.0608 0.1830 -0.2223 0.047 Uiso 0.741(4) 1 calc R U P A 1
C6 C 0.09970(19) 0.4590(7) -0.0789(3) 0.0335(6) Uani 0.741(4) 1 d D . P A 1
C7 C 0.1751(2) 0.6253(7) -0.0172(3) 0.0336(6) Uani 0.741(4) 1 d D . P A 1
H7 H 0.1659 0.7381 0.0500 0.040 Uiso 0.741(4) 1 calc R U P A 1
N1 N 0.00417(19) 0.4389(7) -0.0481(2) 0.0454(7) Uani 0.741(4) 1 d D . P A 1
Br1B Br 0.4334(5) 0.6195(13) 0.1375(6) 0.0501(2) Uani 0.259(4) 1 d D . P A 2
C1B C 0.3769(5) 0.792(2) -0.0217(7) 0.0429(8) Uani 0.259(4) 1 d D . P A 2
H1BA H 0.3688 1.0073 -0.0140 0.052 Uiso 0.259(4) 1 calc R U P A 2
H1BB H 0.4202 0.7569 -0.0797 0.052 Uiso 0.259(4) 1 calc R U P A 2
C2B C 0.2809(4) 0.648(2) -0.0660(6) 0.0348(5) Uani 0.259(4) 1 d D . P A 2
C3B C 0.2725(8) 0.449(6) -0.1631(18) 0.0409(5) Uani 0.259(4) 1 d D . P A 2
H3B H 0.3250 0.4146 -0.2025 0.049 Uiso 0.259(4) 1 calc R U P A 2
C4B C 0.1857(8) 0.301(5) -0.2013(16) 0.0463(7) Uani 0.259(4) 1 d D . P A 2
H4B H 0.1800 0.1690 -0.2665 0.056 Uiso 0.259(4) 1 calc R U P A 2
C5B C 0.1073(5) 0.351(2) -0.1416(8) 0.0391(7) Uani 0.259(4) 1 d D . P A 2
H5B H 0.0480 0.2620 -0.1695 0.047 Uiso 0.259(4) 1 calc R U P A 2
C6B C 0.1187(4) 0.5350(18) -0.0400(6) 0.0335(6) Uani 0.259(4) 1 d D . P A 2
C7B C 0.2053(5) 0.680(2) -0.0017(7) 0.0336(6) Uani 0.259(4) 1 d D . P A 2
H7B H 0.2127 0.7987 0.0674 0.040 Uiso 0.259(4) 1 calc R U P A 2
N1B N 0.0353(4) 0.551(2) 0.0195(7) 0.0454(7) Uani 0.259(4) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.987(3) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.382(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 N1 1.441(4) . ?
C7 H7 0.9300 . ?
N1 N1 1.230(5) 3_565 ?
Br1B C1B 1.987(3) . ?
C1B C2B 1.504(4) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C7B 1.382(4) . ?
C2B C3B 1.392(3) . ?
C3B C4B 1.392(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.394(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.390(4) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.383(4) . ?
C6B N1B 1.440(4) . ?
C7B H7B 0.9300 . ?
N1B N1B 1.115(11) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.04(17) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.9(2) . . ?
C7 C2 C1 120.9(2) . . ?
C3 C2 C1 119.1(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 N1 125.6(3) . . ?
C5 C6 N1 113.8(3) . . ?
C2 C7 C6 120.1(2) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 N1 C6 113.9(3) 3_565 . ?
C2B C1B Br1B 110.0(2) . . ?
C2B C1B H1BA 109.7 . . ?
Br1B C1B H1BA 109.7 . . ?
C2B C1B H1BB 109.7 . . ?
Br1B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?
C7B C2B C3B 119.7(3) . . ?
C7B C2B C1B 120.5(3) . . ?
C3B C2B C1B 119.2(3) . . ?
C4B C3B C2B 120.1(2) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 119.9(3) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C6B C5B C4B 119.3(3) . . ?
C6B C5B H5B 120.4 . . ?
C4B C5B H5B 120.4 . . ?
C7B C6B C5B 120.6(2) . . ?
C7B C6B N1B 125.0(3) . . ?
C5B C6B N1B 114.3(3) . . ?
C2B C7B C6B 120.1(3) . . ?
C2B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
N1B N1B C6B 122.5(7) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 92.0(3) . . . . ?
Br1 C1 C2 C3 -92.7(6) . . . . ?
C7 C2 C3 C4 -1.5(12) . . . . ?
C1 C2 C3 C4 -176.9(7) . . . . ?
C2 C3 C4 C5 0.1(14) . . . . ?
C3 C4 C5 C6 0.7(10) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C4 C5 C6 N1 179.3(5) . . . . ?
C3 C2 C7 C6 2.2(7) . . . . ?
C1 C2 C7 C6 177.5(3) . . . . ?
C5 C6 C7 C2 -1.4(5) . . . . ?
N1 C6 C7 C2 179.4(3) . . . . ?
C7 C6 N1 N1 -7.1(5) . . . 3_565 ?
C5 C6 N1 N1 173.7(4) . . . 3_565 ?
Br1B C1B C2B C7B 62.7(9) . . . . ?
Br1B C1B C2B C3B -108.7(17) . . . . ?
C7B C2B C3B C4B 5(3) . . . . ?
C1B C2B C3B C4B 177(2) . . . . ?
C2B C3B C4B C5B 0(4) . . . . ?
C3B C4B C5B C6B -4(3) . . . . ?
C4B C5B C6B C7B 3(2) . . . . ?
C4B C5B C6B N1B -175.4(15) . . . . ?
C3B C2B C7B C6B -6(2) . . . . ?
C1B C2B C7B C6B -177.0(8) . . . . ?
C5B C6B C7B C2B 1.5(17) . . . . ?
N1B C6B C7B C2B 179.9(9) . . . . ?
C7B C6B N1B N1B 174.1(14) . . . 3_565 ?
C5B C6B N1B N1B -7.4(19) . . . 3_565 ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz126_0m
_database_code_depnum_ccdc_archive 'CCDC 1063372'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   14.0837(18)
_cell_length_b                   4.4538(6)
_cell_length_c                   11.2236(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.2049(18)
_cell_angle_gamma                90
_cell_volume                     694.95(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    1857
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.33

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.816
_shelx_estimated_absorpt_T_min   0.142
_shelx_estimated_absorpt_T_max   0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4789
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6558
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         31.572
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2157
_reflns_number_gt                1442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0378P)²+0.6024P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2157
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.4243(2) 0.5734(6) 0.1374(3) 0.0574(3) Uani 0.718(5) 1 d D . P A 1
C1 C 0.3451(3) 0.8121(10) 0.0081(4) 0.0495(12) Uani 0.718(5) 1 d D . P A 1
H1A H 0.3199 0.9886 0.0429 0.059 Uiso 0.718(5) 1 calc R U P A 1
H1B H 0.3847 0.8782 -0.0501 0.059 Uiso 0.718(5) 1 calc R U P A 1
C2 C 0.2634(3) 0.6237(11) -0.0540(3) 0.0405(8) Uani 0.718(5) 1 d D . P A 1
C3 C 0.2758(4) 0.463(3) -0.1576(8) 0.0483(7) Uani 0.718(5) 1 d D . P A 1
H3 H 0.3351 0.4655 -0.1842 0.058 Uiso 0.718(5) 1 calc R U P A 1
C4 C 0.2000(4) 0.300(2) -0.2208(6) 0.0533(10) Uani 0.718(5) 1 d D . P A 1
H4 H 0.2084 0.1937 -0.2897 0.064 Uiso 0.718(5) 1 calc R U P A 1
C5 C 0.1114(3) 0.2955(12) -0.1805(4) 0.0456(10) Uani 0.718(5) 1 d D . P A 1
H5 H 0.0606 0.1843 -0.2216 0.055 Uiso 0.718(5) 1 calc R U P A 1
C6 C 0.0997(3) 0.4594(11) -0.0782(4) 0.0402(9) Uani 0.718(5) 1 d D . P A 1
C7 C 0.1749(3) 0.6259(10) -0.0167(3) 0.0384(8) Uani 0.718(5) 1 d D . P A 1
H7 H 0.1656 0.7395 0.0500 0.046 Uiso 0.718(5) 1 calc R U P A 1
N1 N 0.0041(3) 0.4402(10) -0.0473(3) 0.0534(11) Uani 0.718(5) 1 d D . P A 1
Br1B Br 0.4328(6) 0.6240(15) 0.1371(7) 0.0574(3) Uani 0.282(5) 1 d D . P A 2
C1B C 0.3765(6) 0.792(3) -0.0230(8) 0.0495(12) Uani 0.282(5) 1 d D . P A 2
H1BA H 0.3686 1.0074 -0.0165 0.059 Uiso 0.282(5) 1 calc R U P A 2
H1BB H 0.4194 0.7542 -0.0808 0.059 Uiso 0.282(5) 1 calc R U P A 2
C2B C 0.2805(5) 0.649(3) -0.0659(7) 0.0405(8) Uani 0.282(5) 1 d D . P A 2
C3B C 0.2714(9) 0.451(6) -0.1640(19) 0.0483(7) Uani 0.282(5) 1 d D . P A 2
H3B H 0.3233 0.4187 -0.2043 0.058 Uiso 0.282(5) 1 calc R U P A 2
C4B C 0.1850(9) 0.302(6) -0.2014(18) 0.0533(10) Uani 0.282(5) 1 d D . P A 2
H4B H 0.1792 0.1701 -0.2663 0.064 Uiso 0.282(5) 1 calc R U P A 2
C5B C 0.1071(6) 0.352(3) -0.1413(10) 0.0456(10) Uani 0.282(5) 1 d D . P A 2
H5B H 0.0479 0.2634 -0.1688 0.055 Uiso 0.282(5) 1 calc R U P A 2
C6B C 0.1190(5) 0.536(2) -0.0398(8) 0.0402(9) Uani 0.282(5) 1 d D . P A 2
C7B C 0.2058(6) 0.678(3) -0.0011(8) 0.0384(8) Uani 0.282(5) 1 d D . P A 2
H7B H 0.2137 0.7942 0.0687 0.046 Uiso 0.282(5) 1 calc R U P A 2
N1B N 0.0358(5) 0.551(3) 0.0205(8) 0.0534(11) Uani 0.282(5) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.991(4) . ?
C1 C2 1.502(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.378(5) . ?
C2 C3 1.400(4) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(5) . ?
C6 N1 1.446(5) . ?
C7 H7 0.9300 . ?
N1 N1 1.210(7) 3_565 ?
Br1B C1B 1.991(4) . ?
C1B C2B 1.502(5) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C7B 1.378(5) . ?
C2B C3B 1.400(4) . ?
C3B C4B 1.389(5) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.394(6) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.392(6) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.383(5) . ?
C6B N1B 1.445(5) . ?
C7B H7B 0.9300 . ?
N1B N1B 1.135(12) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.8(2) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 121.2(3) . . ?
C3 C2 C1 118.8(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 N1 125.4(4) . . ?
C5 C6 N1 113.9(4) . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 N1 C6 114.1(5) 3_565 . ?
C2B C1B Br1B 109.7(2) . . ?
C2B C1B H1BA 109.7 . . ?
Br1B C1B H1BA 109.7 . . ?
C2B C1B H1BB 109.7 . . ?
Br1B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?
C7B C2B C3B 119.6(3) . . ?
C7B C2B C1B 120.9(4) . . ?
C3B C2B C1B 118.9(4) . . ?
C4B C3B C2B 120.2(3) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 119.8(3) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C6B C5B C4B 119.3(3) . . ?
C6B C5B H5B 120.4 . . ?
C4B C5B H5B 120.4 . . ?
C7B C6B C5B 120.7(3) . . ?
C7B C6B N1B 125.0(4) . . ?
C5B C6B N1B 114.2(4) . . ?
C2B C7B C6B 120.1(3) . . ?
C2B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
N1B N1B C6B 121.8(9) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 92.6(5) . . . . ?
Br1 C1 C2 C3 -92.8(7) . . . . ?
C7 C2 C3 C4 -1.7(14) . . . . ?
C1 C2 C3 C4 -176.5(9) . . . . ?
C2 C3 C4 C5 -0.2(17) . . . . ?
C3 C4 C5 C6 1.0(13) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
C4 C5 C6 N1 179.0(6) . . . . ?
C3 C2 C7 C6 2.8(9) . . . . ?
C1 C2 C7 C6 177.5(4) . . . . ?
C5 C6 C7 C2 -2.0(7) . . . . ?
N1 C6 C7 C2 179.2(4) . . . . ?
C7 C6 N1 N1 -7.4(8) . . . 3_565 ?
C5 C6 N1 N1 173.8(6) . . . 3_565 ?
Br1B C1B C2B C7B 61.5(11) . . . . ?
Br1B C1B C2B C3B -110.1(17) . . . . ?
C7B C2B C3B C4B 5(4) . . . . ?
C1B C2B C3B C4B 176(2) . . . . ?
C2B C3B C4B C5B 0(4) . . . . ?
C3B C4B C5B C6B -4(4) . . . . ?
C4B C5B C6B C7B 3(2) . . . . ?
C4B C5B C6B N1B -175.1(18) . . . . ?
C3B C2B C7B C6B -6(2) . . . . ?
C1B C2B C7B C6B -177.8(10) . . . . ?
C5B C6B C7B C2B 3(2) . . . . ?
N1B C6B C7B C2B -180.0(12) . . . . ?
C7B C6B N1B N1B 173.8(19) . . . 3_565 ?
C5B C6B N1B N1B -9(3) . . . 3_565 ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz127_0m
_database_code_depnum_ccdc_archive 'CCDC 1063373'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   14.105(3)
_cell_length_b                   4.4657(10)
_cell_length_c                   11.245(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.262(3)
_cell_angle_gamma                90
_cell_volume                     699.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    330(2)
_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.97

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.781
_shelx_estimated_absorpt_T_min   0.143
_shelx_estimated_absorpt_T_max   0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3950
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      330(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6764
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         31.487
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2196
_reflns_number_gt                1312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0373P)²+0.1498P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.4233(2) 0.5705(6) 0.1369(3) 0.0638(4) Uani 0.667(4) 1 d D . P A 1
C1 C 0.3434(3) 0.8104(9) 0.0092(4) 0.0530(11) Uani 0.667(4) 1 d D . P A 1
H1A H 0.3176 0.9837 0.0451 0.064 Uiso 0.667(4) 1 calc R U P A 1
H1B H 0.3828 0.8807 -0.0482 0.064 Uiso 0.667(4) 1 calc R U P A 1
C2 C 0.2627(2) 0.6232(11) -0.0543(3) 0.0457(7) Uani 0.667(4) 1 d D . P A 1
C3 C 0.2752(4) 0.464(3) -0.1569(10) 0.0537(6) Uani 0.667(4) 1 d D . P A 1
H3 H 0.3347 0.4650 -0.1825 0.064 Uiso 0.667(4) 1 calc R U P A 1
C4 C 0.2001(4) 0.302(2) -0.2214(7) 0.0574(10) Uani 0.667(4) 1 d D . P A 1
H4 H 0.2084 0.2007 -0.2911 0.069 Uiso 0.667(4) 1 calc R U P A 1
C5 C 0.1116(3) 0.2942(12) -0.1805(4) 0.0477(9) Uani 0.667(4) 1 d D . P A 1
H5 H 0.0612 0.1811 -0.2213 0.057 Uiso 0.667(4) 1 calc R U P A 1
C6 C 0.0995(2) 0.4558(10) -0.0788(4) 0.0407(8) Uani 0.667(4) 1 d D . P A 1
C7 C 0.1740(3) 0.6214(10) -0.0169(4) 0.0410(8) Uani 0.667(4) 1 d D . P A 1
H7 H 0.1645 0.7323 0.0502 0.049 Uiso 0.667(4) 1 calc R U P A 1
N1 N 0.0044(2) 0.4397(10) -0.0477(3) 0.0579(10) Uani 0.667(4) 1 d D . P A 1
Br1B Br 0.4328(5) 0.6237(13) 0.1380(6) 0.0638(4) Uani 0.333(4) 1 d D . P A 2
C1B C 0.3737(5) 0.794(2) -0.0201(7) 0.0530(11) Uani 0.333(4) 1 d D . P A 2
H1BA H 0.3638 1.0077 -0.0118 0.064 Uiso 0.333(4) 1 calc R U P A 2
H1BB H 0.4165 0.7650 -0.0785 0.064 Uiso 0.333(4) 1 calc R U P A 2
C2B C 0.2794(4) 0.645(2) -0.0635(6) 0.0457(7) Uani 0.333(4) 1 d D . P A 2
C3B C 0.2704(8) 0.452(6) -0.1620(19) 0.0537(6) Uani 0.333(4) 1 d D . P A 2
H3B H 0.3224 0.4233 -0.2023 0.064 Uiso 0.333(4) 1 calc R U P A 2
C4B C 0.1850(8) 0.303(5) -0.2008(16) 0.0574(10) Uani 0.333(4) 1 d D . P A 2
H4B H 0.1799 0.1707 -0.2655 0.069 Uiso 0.333(4) 1 calc R U P A 2
C5B C 0.1063(5) 0.352(2) -0.1419(8) 0.0477(9) Uani 0.333(4) 1 d D . P A 2
H5B H 0.0473 0.2635 -0.1700 0.057 Uiso 0.333(4) 1 calc R U P A 2
C6B C 0.1171(5) 0.5353(18) -0.0411(6) 0.0407(8) Uani 0.333(4) 1 d D . P A 2
C7B C 0.2029(5) 0.679(2) -0.0019(7) 0.0410(8) Uani 0.333(4) 1 d D . P A 2
H7B H 0.2092 0.8007 0.0661 0.049 Uiso 0.333(4) 1 calc R U P A 2
N1B N 0.0349(4) 0.550(2) 0.0201(7) 0.0579(10) Uani 0.333(4) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.990(3) . ?
C1 C2 1.498(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.383(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 N1 1.442(4) . ?
C7 H7 0.9300 . ?
N1 N1 1.224(7) 3_565 ?
Br1B C1B 1.990(3) . ?
C1B C2B 1.498(4) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C7B 1.383(4) . ?
C2B C3B 1.392(4) . ?
C3B C4B 1.385(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.398(5) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.385(5) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.378(5) . ?
C6B N1B 1.442(4) . ?
C7B H7B 0.9300 . ?
N1B N1B 1.109(12) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.0(2) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.4(3) . . ?
C7 C2 C1 120.9(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 N1 124.5(3) . . ?
C5 C6 N1 114.7(3) . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 N1 C6 114.8(5) 3_565 . ?
C2B C1B Br1B 110.1(2) . . ?
C2B C1B H1BA 109.7 . . ?
Br1B C1B H1BA 109.7 . . ?
C2B C1B H1BB 109.7 . . ?
Br1B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?
C7B C2B C3B 119.3(3) . . ?
C7B C2B C1B 120.7(3) . . ?
C3B C2B C1B 119.9(3) . . ?
C4B C3B C2B 120.7(3) . . ?
C4B C3B H3B 119.6 . . ?
C2B C3B H3B 119.6 . . ?
C3B C4B C5B 119.4(3) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 119.3(3) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C7B C6B C5B 120.8(3) . . ?
C7B C6B N1B 123.9(4) . . ?
C5B C6B N1B 115.2(4) . . ?
C6B C7B C2B 120.2(3) . . ?
C6B C7B H7B 119.9 . . ?
C2B C7B H7B 119.9 . . ?
N1B N1B C6B 121.1(8) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 92.6(5) . . . . ?
Br1 C1 C2 C3 -91.5(9) . . . . ?
C7 C2 C3 C4 -0.3(18) . . . . ?
C1 C2 C3 C4 -176.3(11) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C3 C4 C5 C6 2.3(16) . . . . ?
C4 C5 C6 C7 -0.7(9) . . . . ?
C4 C5 C6 N1 177.8(7) . . . . ?
C5 C6 C7 C2 -1.4(7) . . . . ?
N1 C6 C7 C2 -179.7(4) . . . . ?
C3 C2 C7 C6 1.9(11) . . . . ?
C1 C2 C7 C6 177.8(4) . . . . ?
C7 C6 N1 N1 -7.7(8) . . . 3_565 ?
C5 C6 N1 N1 173.9(6) . . . 3_565 ?
Br1B C1B C2B C7B 65.9(10) . . . . ?
Br1B C1B C2B C3B -109.8(18) . . . . ?
C7B C2B C3B C4B 2(4) . . . . ?
C1B C2B C3B C4B 178(2) . . . . ?
C2B C3B C4B C5B 2(4) . . . . ?
C3B C4B C5B C6B -4(3) . . . . ?
C4B C5B C6B C7B 3(2) . . . . ?
C4B C5B C6B N1B -174.3(16) . . . . ?
C5B C6B C7B C2B 0.4(17) . . . . ?
N1B C6B C7B C2B 177.6(10) . . . . ?
C3B C2B C7B C6B -3(2) . . . . ?
C1B C2B C7B C6B -178.5(8) . . . . ?
C7B C6B N1B N1B 173.4(15) . . . 3_565 ?
C5B C6B N1B N1B -9.3(19) . . . 3_565 ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz128_0m
_database_code_depnum_ccdc_archive 'CCDC 1063374'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          419-420K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   14.129(5)
_cell_length_b                   4.4805(14)
_cell_length_c                   11.264(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.369(5)
_cell_angle_gamma                90
_cell_volume                     703.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    375(2)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.27

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.470
_exptl_absorpt_coefficient_mu    5.744
_shelx_estimated_absorpt_T_min   0.144
_shelx_estimated_absorpt_T_max   0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3576
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      375(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 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7885
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.922
_diffrn_reflns_theta_max         31.703
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2250
_reflns_number_gt                1275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0420P)²+0.1054P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2250
_refine_ls_number_parameters     111
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.4226(2) 0.5670(6) 0.1372(3) 0.0764(4) Uani 0.639(4) 1 d D . P A 1
C1 C 0.3428(3) 0.8073(10) 0.0107(4) 0.0640(11) Uani 0.639(4) 1 d D . P A 1
H1A H 0.3171 0.9795 0.0469 0.077 Uiso 0.639(4) 1 calc R U P A 1
H1B H 0.3819 0.8783 -0.0467 0.077 Uiso 0.639(4) 1 calc R U P A 1
C2 C 0.2619(2) 0.6205(11) -0.0530(3) 0.0555(7) Uani 0.639(4) 1 d D . P A 1
C3 C 0.2746(5) 0.467(3) -0.1564(10) 0.0662(7) Uani 0.639(4) 1 d D . P A 1
H3 H 0.3338 0.4711 -0.1824 0.079 Uiso 0.639(4) 1 calc R U P A 1
C4 C 0.1991(4) 0.306(2) -0.2210(7) 0.0703(12) Uani 0.639(4) 1 d D . P A 1
H4 H 0.2072 0.2055 -0.2908 0.084 Uiso 0.639(4) 1 calc R U P A 1
C5 C 0.1108(3) 0.2968(12) -0.1800(4) 0.0580(9) Uani 0.639(4) 1 d D . P A 1
H5 H 0.0604 0.1846 -0.2208 0.070 Uiso 0.639(4) 1 calc R U P A 1
C6 C 0.0996(2) 0.4568(9) -0.0781(4) 0.0495(8) Uani 0.639(4) 1 d D . P A 1
C7 C 0.1734(3) 0.6212(10) -0.0166(4) 0.0502(8) Uani 0.639(4) 1 d D . P A 1
H7 H 0.1638 0.7335 0.0498 0.060 Uiso 0.639(4) 1 calc R U P A 1
N1 N 0.0046(2) 0.4392(10) -0.0467(3) 0.0682(10) Uani 0.639(4) 1 d D . P A 1
Br1B Br 0.4320(4) 0.6271(10) 0.1372(5) 0.0764(4) Uani 0.361(4) 1 d D . P A 2
C1B C 0.3726(4) 0.7946(19) -0.0206(6) 0.0640(11) Uani 0.361(4) 1 d D . P A 2
H1BA H 0.3626 1.0074 -0.0128 0.077 Uiso 0.361(4) 1 calc R U P A 2
H1BB H 0.4152 0.7650 -0.0790 0.077 Uiso 0.361(4) 1 calc R U P A 2
C2B C 0.2784(3) 0.644(2) -0.0634(5) 0.0555(7) Uani 0.361(4) 1 d D . P A 2
C3B C 0.2704(8) 0.449(6) -0.1605(18) 0.0662(7) Uani 0.361(4) 1 d D . P A 2
H3B H 0.3223 0.4198 -0.2004 0.079 Uiso 0.361(4) 1 calc R U P A 2
C4B C 0.1847(7) 0.298(4) -0.1983(14) 0.0703(12) Uani 0.361(4) 1 d D . P A 2
H4B H 0.1800 0.1618 -0.2612 0.084 Uiso 0.361(4) 1 calc R U P A 2
C5B C 0.1058(5) 0.353(2) -0.1408(7) 0.0580(9) Uani 0.361(4) 1 d D . P A 2
H5B H 0.0466 0.2671 -0.1694 0.070 Uiso 0.361(4) 1 calc R U P A 2
C6B C 0.1173(4) 0.5367(16) -0.0407(6) 0.0495(8) Uani 0.361(4) 1 d D . P A 2
C7B C 0.2029(5) 0.676(2) -0.0009(6) 0.0502(8) Uani 0.361(4) 1 d D . P A 2
H7B H 0.2101 0.7916 0.0684 0.060 Uiso 0.361(4) 1 calc R U P A 2
N1B N 0.0352(4) 0.552(2) 0.0205(6) 0.0682(10) Uani 0.361(4) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.985(3) . ?
C1 C2 1.502(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.377(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(4) . ?
C6 N1 1.444(4) . ?
C7 H7 0.9300 . ?
N1 N1 1.211(7) 3_565 ?
Br1B C1B 1.985(3) . ?
C1B C2B 1.501(4) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C7B 1.377(4) . ?
C2B C3B 1.389(4) . ?
C3B C4B 1.391(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.399(5) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.384(5) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.370(4) . ?
C6B N1B 1.444(4) . ?
C7B H7B 0.9300 . ?
N1B N1B 1.128(11) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.9(2) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.9(3) . . ?
C7 C2 C1 120.9(3) . . ?
C3 C2 C1 119.0(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 N1 124.6(3) . . ?
C5 C6 N1 114.3(3) . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 N1 C6 115.1(5) 3_565 . ?
C2B C1B Br1B 109.9(2) . . ?
C2B C1B H1BA 109.7 . . ?
Br1B C1B H1BA 109.7 . . ?
C2B C1B H1BB 109.7 . . ?
Br1B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?
C7B C2B C3B 119.8(3) . . ?
C7B C2B C1B 120.6(3) . . ?
C3B C2B C1B 119.3(3) . . ?
C2B C3B C4B 120.1(3) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B C5B 119.5(3) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C6B C5B C4B 119.0(3) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C7B C6B C5B 121.1(3) . . ?
C7B C6B N1B 123.9(4) . . ?
C5B C6B N1B 114.9(4) . . ?
C6B C7B C2B 120.1(3) . . ?
C6B C7B H7B 119.9 . . ?
C2B C7B H7B 119.9 . . ?
N1B N1B C6B 120.6(7) 3_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 93.6(5) . . . . ?
Br1 C1 C2 C3 -92.2(10) . . . . ?
C7 C2 C3 C4 -2.0(19) . . . . ?
C1 C2 C3 C4 -176.3(11) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 C6 2.2(15) . . . . ?
C4 C5 C6 C7 -0.5(9) . . . . ?
C4 C5 C6 N1 177.9(7) . . . . ?
C5 C6 C7 C2 -2.5(7) . . . . ?
N1 C6 C7 C2 179.2(4) . . . . ?
C3 C2 C7 C6 3.7(11) . . . . ?
C1 C2 C7 C6 177.9(4) . . . . ?
C7 C6 N1 N1 -6.5(8) . . . 3_565 ?
C5 C6 N1 N1 175.2(6) . . . 3_565 ?
Br1B C1B C2B C7B 65.0(9) . . . . ?
Br1B C1B C2B C3B -109.2(17) . . . . ?
C7B C2B C3B C4B 3(3) . . . . ?
C1B C2B C3B C4B 177(2) . . . . ?
C2B C3B C4B C5B 3(4) . . . . ?
C3B C4B C5B C6B -6(3) . . . . ?
C4B C5B C6B C7B 3.1(18) . . . . ?
C4B C5B C6B N1B -173.1(14) . . . . ?
C5B C6B C7B C2B 2.7(15) . . . . ?
N1B C6B C7B C2B 178.5(9) . . . . ?
C3B C2B C7B C6B -6(2) . . . . ?
C1B C2B C7B C6B -180.0(7) . . . . ?
C7B C6B N1B N1B 175.1(13) . . . 3_565 ?
C5B C6B N1B N1B -8.8(17) . . . 3_565 ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_12mz151_0m2plus3
_database_code_depnum_ccdc_archive 'CCDC 1063375'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   12.9324(11)
_cell_length_b                   4.4704(4)
_cell_length_c                   11.5909(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.5920(10)
_cell_angle_gamma                90
_cell_volume                     653.99(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9310
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.86

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.180
_shelx_estimated_absorpt_T_min   0.132
_shelx_estimated_absorpt_T_max   0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2504
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS-2008/1
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14059
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.228
_diffrn_reflns_theta_max         30.896
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2062
_reflns_number_gt                1933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.2716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2062
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43784(9) 1.1449(3) 0.65843(10) 0.01619(13) Uani 0.768(3) 1 d D . P A
1
C1 C -0.3475(3) 1.3429(11) 0.5635(4) 0.0166(8) Uani 0.768(3) 1 d D . P A 1
H1A H -0.3898 1.3858 0.4832 0.020 Uiso 0.768(3) 1 calc R U P A 1
H1B H -0.3207 1.5350 0.6009 0.020 Uiso 0.768(3) 1 calc R U P A 1
C2 C -0.2567(6) 1.145(3) 0.5555(6) 0.0118(3) Uani 0.768(3) 1 d D . P A 1
C3 C -0.1734(3) 1.1047(10) 0.6537(4) 0.0120(5) Uani 0.768(3) 1 d D . P A 1
H3 H -0.1738 1.2088 0.7251 0.014 Uiso 0.768(3) 1 calc R U P A 1
C4 C -0.08967(18) 0.9129(5) 0.6476(2) 0.0118(4) Uani 0.768(3) 1 d D . P A 1
H4 H -0.0336 0.8854 0.7149 0.014 Uiso 0.768(3) 1 calc R U P A 1
C5 C -0.08813(16) 0.7613(4) 0.5428(2) 0.0101(4) Uani 0.768(3) 1 d D . P A 1
C6 C -0.1690(2) 0.8043(6) 0.4438(2) 0.0132(4) Uani 0.768(3) 1 d D . P A 1
H6 H -0.1671 0.7054 0.3718 0.016 Uiso 0.768(3) 1 calc R U P A 1
C7 C -0.2537(4) 0.9945(14) 0.4507(4) 0.0146(6) Uani 0.768(3) 1 d D . P A 1
H7 H -0.3096 1.0215 0.3832 0.018 Uiso 0.768(3) 1 calc R U P A 1
N1 N -0.00001(14) 0.5655(4) 0.54816(14) 0.0123(3) Uani 0.768(3) 1 d . . P A 1
Br1B Br -0.4274(3) 1.1299(11) 0.6719(4) 0.01619(13) Uani 0.232(3) 1 d D . P A 2
C1B C -0.3359(15) 1.353(4) 0.5841(18) 0.0166(8) Uani 0.232(3) 1 d D . P A 2
H1B1 H -0.3796 1.4347 0.5100 0.020 Uiso 0.232(3) 1 calc R U P A 2
H1B2 H -0.3010 1.5213 0.6327 0.020 Uiso 0.232(3) 1 calc R U P A 2
C2B C -0.254(2) 1.144(10) 0.5562(19) 0.0118(3) Uani 0.232(3) 1 d D . P A 2
C3B C -0.1618(13) 1.068(4) 0.6411(15) 0.0120(5) Uani 0.232(3) 1 d D . P A 2
H3B H -0.1488 1.1526 0.7181 0.014 Uiso 0.232(3) 1 calc R U P A 2
C4B C -0.0903(7) 0.8673(19) 0.6099(8) 0.0118(4) Uani 0.232(3) 1 d D . P A 2
H4B H -0.0283 0.8117 0.6662 0.014 Uiso 0.232(3) 1 calc R U P A 2
C5B C -0.1093(6) 0.7492(17) 0.4979(7) 0.0101(4) Uani 0.232(3) 1 d D . P A 2
C6B C -0.1970(8) 0.826(2) 0.4153(9) 0.0132(4) Uani 0.232(3) 1 d D . P A 2
H6B H -0.2073 0.7433 0.3381 0.016 Uiso 0.232(3) 1 calc R U P A 2
C7B C -0.2711(15) 1.020(6) 0.4414(16) 0.0146(6) Uani 0.232(3) 1 d D . P A 2
H7B H -0.3326 1.0706 0.3833 0.018 Uiso 0.232(3) 1 calc R U P A 2
N1B N -0.0387(5) 0.5377(14) 0.4599(5) 0.0123(3) Uani 0.232(3) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.979(4) . ?
C1 C2 1.490(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.396(5) . ?
C2 C3 1.398(5) . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 N1 1.428(3) . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.261(3) 3_566 ?
Br1B C1B 1.987(15) . ?
C1B C2B 1.497(14) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.412(14) . ?
C2B C7B 1.414(14) . ?
C3B C4B 1.392(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.374(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.358(10) . ?
C5B N1B 1.448(10) . ?
C6B C7B 1.376(13) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.256(12) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.7(6) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 119.0(4) . . ?
C7 C2 C1 120.8(4) . . ?
C3 C2 C1 120.2(4) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 N1 124.9(2) . . ?
C4 C5 N1 115.0(2) . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 N1 C5 113.6(2) 3_566 . ?
C2B C1B Br1B 109(2) . . ?
C2B C1B H1B1 109.9 . . ?
Br1B C1B H1B1 109.9 . . ?
C2B C1B H1B2 109.9 . . ?
Br1B C1B H1B2 109.9 . . ?
H1B1 C1B H1B2 108.3 . . ?
C3B C2B C7B 119.7(14) . . ?
C3B C2B C1B 121.9(15) . . ?
C7B C2B C1B 118.3(14) . . ?
C4B C3B C2B 118.9(13) . . ?
C4B C3B H3B 120.6 . . ?
C2B C3B H3B 120.6 . . ?
C5B C4B C3B 120.1(10) . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C6B C5B C4B 121.3(8) . . ?
C6B C5B N1B 115.8(8) . . ?
C4B C5B N1B 123.0(7) . . ?
C5B C6B C7B 121.3(10) . . ?
C5B C6B H6B 119.4 . . ?
C7B C6B H6B 119.4 . . ?
C6B C7B C2B 118.8(13) . . ?
C6B C7B H7B 120.6 . . ?
C2B C7B H7B 120.6 . . ?
N1B N1B C5B 113.8(8) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 106.3(11) . . . . ?
Br1 C1 C2 C3 -73.1(12) . . . . ?
C7 C2 C3 C4 -1.3(16) . . . . ?
C1 C2 C3 C4 178.2(8) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 N1 -178.4(3) . . . . ?
C4 C5 C6 C7 -1.7(5) . . . . ?
N1 C5 C6 C7 177.6(4) . . . . ?
C3 C2 C7 C6 0.5(16) . . . . ?
C1 C2 C7 C6 -178.9(8) . . . . ?
C5 C6 C7 C2 1.0(11) . . . . ?
C6 C5 N1 N1 1.5(3) . . . 3_566 ?
C4 C5 N1 N1 -179.1(2) . . . 3_566 ?
Br1B C1B C2B C3B -80(4) . . . . ?
Br1B C1B C2B C7B 100(4) . . . . ?
C7B C2B C3B C4B -1(5) . . . . ?
C1B C2B C3B C4B 178(3) . . . . ?
C2B C3B C4B C5B 1(3) . . . . ?
C3B C4B C5B C6B 0.4(16) . . . . ?
C3B C4B C5B N1B -179.5(12) . . . . ?
C4B C5B C6B C7B -1(2) . . . . ?
N1B C5B C6B C7B 178.7(16) . . . . ?
C5B C6B C7B C2B 1(4) . . . . ?
C3B C2B C7B C6B 0(6) . . . . ?
C1B C2B C7B C6B -179(3) . . . . ?
C6B C5B N1B N1B -176.9(8) . . . 3_566 ?
C4B C5B N1B N1B 3.0(12) . . . 3_566 ?

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.128

####################################################################### 
# 
# 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_12mz152_0m
_database_code_depnum_ccdc_archive 'CCDC 1063376'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   12.9484(15)
_cell_length_b                   4.4854(5)
_cell_length_c                   11.6092(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.5452(14)
_cell_angle_gamma                90
_cell_volume                     658.15(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4307
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      31.60

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.141
_shelx_estimated_absorpt_T_min   0.133
_shelx_estimated_absorpt_T_max   0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2489
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7391
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.224
_diffrn_reflns_theta_max         31.911
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2156
_reflns_number_gt                1907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2156
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43720(10) 1.1444(3) 0.65867(12) 0.02403(14) Uani 0.771(3) 1 d D . P A
1
C1 C -0.3471(4) 1.3399(12) 0.5635(4) 0.0226(9) Uani 0.771(3) 1 d D . P A 1
H1A H -0.3894 1.3822 0.4834 0.027 Uiso 0.771(3) 1 calc R U P A 1
H1B H -0.3202 1.5315 0.6006 0.027 Uiso 0.771(3) 1 calc R U P A 1
C2 C -0.2565(6) 1.141(3) 0.5555(6) 0.0168(4) Uani 0.771(3) 1 d D . P A 1
C3 C -0.1729(3) 1.1043(10) 0.6530(4) 0.0166(5) Uani 0.771(3) 1 d D . P A 1
H3 H -0.1727 1.2104 0.7239 0.020 Uiso 0.771(3) 1 calc R U P A 1
C4 C -0.08966(18) 0.9117(5) 0.6468(2) 0.0161(4) Uani 0.771(3) 1 d D . P A 1
H4 H -0.0338 0.8838 0.7140 0.019 Uiso 0.771(3) 1 calc R U P A 1
C5 C -0.08827(17) 0.7607(4) 0.5425(2) 0.0135(4) Uani 0.771(3) 1 d D . P A 1
C6 C -0.1693(2) 0.8024(6) 0.4442(2) 0.0186(5) Uani 0.771(3) 1 d D . P A 1
H6 H -0.1677 0.7020 0.3725 0.022 Uiso 0.771(3) 1 calc R U P A 1
C7 C -0.2534(4) 0.9925(18) 0.4506(5) 0.0208(6) Uani 0.771(3) 1 d D . P A 1
H7 H -0.3089 1.0208 0.3830 0.025 Uiso 0.771(3) 1 calc R U P A 1
N1 N 0.00005(14) 0.5659(4) 0.54805(15) 0.0166(3) Uani 0.771(3) 1 d . . P A 1
Br1B Br -0.4261(4) 1.1267(13) 0.6723(4) 0.02403(14) Uani 0.229(3) 1 d D . P A 2
C1B C -0.3354(15) 1.348(4) 0.5853(18) 0.0226(9) Uani 0.229(3) 1 d D . P A 2
H1B1 H -0.3791 1.4289 0.5112 0.027 Uiso 0.229(3) 1 calc R U P A 2
H1B2 H -0.3012 1.5170 0.6337 0.027 Uiso 0.229(3) 1 calc R U P A 2
C2B C -0.253(2) 1.144(10) 0.557(2) 0.0168(4) Uani 0.229(3) 1 d D . P A 2
C3B C -0.1614(14) 1.062(4) 0.6414(15) 0.0166(5) Uani 0.229(3) 1 d D . P A 2
H3B H -0.1488 1.1393 0.7194 0.020 Uiso 0.229(3) 1 calc R U P A 2
C4B C -0.0903(8) 0.868(2) 0.6081(8) 0.0161(4) Uani 0.229(3) 1 d D . P A 2
H4B H -0.0271 0.8166 0.6630 0.019 Uiso 0.229(3) 1 calc R U P A 2
C5B C -0.1097(7) 0.7485(17) 0.4976(7) 0.0135(4) Uani 0.229(3) 1 d D . P A 2
C6B C -0.1969(8) 0.826(3) 0.4158(9) 0.0186(5) Uani 0.229(3) 1 d D . P A 2
H6B H -0.2070 0.7479 0.3380 0.022 Uiso 0.229(3) 1 calc R U P A 2
C7B C -0.2709(18) 1.015(7) 0.4440(19) 0.0208(6) Uani 0.229(3) 1 d D . P A 2
H7B H -0.3341 1.0579 0.3876 0.025 Uiso 0.229(3) 1 calc R U P A 2
N1B N -0.0379(5) 0.5378(14) 0.4605(5) 0.0166(3) Uani 0.229(3) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.977(4) . ?
C1 C2 1.492(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.396(5) . ?
C2 C7 1.397(5) . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 N1 1.429(3) . ?
C6 C7 1.398(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.262(3) 3_566 ?
Br1B C1B 1.974(15) . ?
C1B C2B 1.496(14) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.408(14) . ?
C2B C7B 1.411(14) . ?
C3B C4B 1.383(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.362(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.353(10) . ?
C5B N1B 1.455(10) . ?
C6B C7B 1.372(14) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.237(13) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.7(6) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C7 119.1(4) . . ?
C3 C2 C1 120.1(4) . . ?
C7 C2 C1 120.8(4) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 N1 125.1(2) . . ?
C4 C5 N1 114.8(2) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.5(4) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N1 N1 C5 113.5(2) 3_566 . ?
C2B C1B Br1B 110(2) . . ?
C2B C1B H1B1 109.7 . . ?
Br1B C1B H1B1 109.7 . . ?
C2B C1B H1B2 109.7 . . ?
Br1B C1B H1B2 109.7 . . ?
H1B1 C1B H1B2 108.2 . . ?
C3B C2B C7B 119.0(14) . . ?
C3B C2B C1B 122.8(15) . . ?
C7B C2B C1B 118.0(15) . . ?
C4B C3B C2B 118.7(13) . . ?
C4B C3B H3B 120.7 . . ?
C2B C3B H3B 120.7 . . ?
C5B C4B C3B 120.9(10) . . ?
C5B C4B H4B 119.5 . . ?
C3B C4B H4B 119.5 . . ?
C6B C5B C4B 121.0(8) . . ?
C6B C5B N1B 116.6(8) . . ?
C4B C5B N1B 122.4(8) . . ?
C5B C6B C7B 120.7(11) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B C2B 119.5(14) . . ?
C6B C7B H7B 120.2 . . ?
C2B C7B H7B 120.2 . . ?
N1B N1B C5B 114.4(8) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -73.7(11) . . . . ?
Br1 C1 C2 C7 106.9(11) . . . . ?
C7 C2 C3 C4 -2.5(16) . . . . ?
C1 C2 C3 C4 178.1(7) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 N1 -178.8(3) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
N1 C5 C6 C7 178.0(5) . . . . ?
C3 C2 C7 C6 1.8(17) . . . . ?
C1 C2 C7 C6 -178.8(8) . . . . ?
C5 C6 C7 C2 0.0(12) . . . . ?
C6 C5 N1 N1 1.5(3) . . . 3_566 ?
C4 C5 N1 N1 -179.3(2) . . . 3_566 ?
Br1B C1B C2B C3B -78(4) . . . . ?
Br1B C1B C2B C7B 98(4) . . . . ?
C7B C2B C3B C4B 3(5) . . . . ?
C1B C2B C3B C4B 179(3) . . . . ?
C2B C3B C4B C5B -2(3) . . . . ?
C3B C4B C5B C6B 2.6(17) . . . . ?
C3B C4B C5B N1B -178.5(12) . . . . ?
C4B C5B C6B C7B -3(2) . . . . ?
N1B C5B C6B C7B 178(2) . . . . ?
C5B C6B C7B C2B 4(4) . . . . ?
C3B C2B C7B C6B -4(6) . . . . ?
C1B C2B C7B C6B -180(3) . . . . ?
C6B C5B N1B N1B -176.6(9) . . . 3_566 ?
C4B C5B N1B N1B 4.5(12) . . . 3_566 ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_12mz153_0m
_database_code_depnum_ccdc_archive 'CCDC 1063377'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   12.9648(11)
_cell_length_b                   4.5026(4)
_cell_length_c                   11.6333(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.4990(10)
_cell_angle_gamma                90
_cell_volume                     663.00(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    7325
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      31.84

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.096
_shelx_estimated_absorpt_T_min   0.134
_shelx_estimated_absorpt_T_max   0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2533
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   SADABS-2008/1
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14654
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         32.040
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2170
_reflns_number_gt                1908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.2202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43659(10) 1.1438(4) 0.65891(12) 0.03244(16) Uani 0.778(4) 1 d D . P A
1
C1 C -0.3464(4) 1.3369(12) 0.5636(4) 0.0291(10) Uani 0.778(4) 1 d D . P A 1
H1A H -0.3885 1.3788 0.4836 0.035 Uiso 0.778(4) 1 calc R U P A 1
H1B H -0.3193 1.5278 0.6004 0.035 Uiso 0.778(4) 1 calc R U P A 1
C2 C -0.2563(6) 1.138(3) 0.5558(6) 0.0218(5) Uani 0.778(4) 1 d D . P A 1
C3 C -0.1725(4) 1.1023(10) 0.6528(4) 0.0221(6) Uani 0.778(4) 1 d D . P A 1
H3 H -0.1720 1.2091 0.7233 0.027 Uiso 0.778(4) 1 calc R U P A 1
C4 C -0.0895(2) 0.9108(6) 0.6464(3) 0.0211(4) Uani 0.778(4) 1 d D . P A 1
H4 H -0.0336 0.8835 0.7134 0.025 Uiso 0.778(4) 1 calc R U P A 1
C5 C -0.08803(19) 0.7598(5) 0.5428(2) 0.0180(4) Uani 0.778(4) 1 d D . P A 1
C6 C -0.1691(2) 0.8012(7) 0.4445(3) 0.0241(5) Uani 0.778(4) 1 d D . P A 1
H6 H -0.1671 0.7030 0.3727 0.029 Uiso 0.778(4) 1 calc R U P A 1
C7 C -0.2534(5) 0.9876(16) 0.4515(5) 0.0260(7) Uani 0.778(4) 1 d D . P A 1
H7 H -0.3095 1.0127 0.3846 0.031 Uiso 0.778(4) 1 calc R U P A 1
N1 N -0.00015(16) 0.5657(5) 0.54771(17) 0.0213(4) Uani 0.778(4) 1 d . . P A 1
Br1B Br -0.4243(4) 1.1242(14) 0.6730(5) 0.03244(16) Uani 0.222(4) 1 d D . P A 2
C1B C -0.3344(16) 1.346(5) 0.586(2) 0.0291(10) Uani 0.222(4) 1 d D . P A 2
H1B1 H -0.3785 1.4272 0.5125 0.035 Uiso 0.222(4) 1 calc R U P A 2
H1B2 H -0.3001 1.5136 0.6344 0.035 Uiso 0.222(4) 1 calc R U P A 2
C2B C -0.252(2) 1.144(10) 0.557(2) 0.0218(5) Uani 0.222(4) 1 d D . P A 2
C3B C -0.1616(15) 1.058(4) 0.6404(16) 0.0221(6) Uani 0.222(4) 1 d D . P A 2
H3B H -0.1500 1.1318 0.7187 0.027 Uiso 0.222(4) 1 calc R U P A 2
C4B C -0.0896(8) 0.866(2) 0.6081(9) 0.0211(4) Uani 0.222(4) 1 d D . P A 2
H4B H -0.0264 0.8158 0.6628 0.025 Uiso 0.222(4) 1 calc R U P A 2
C5B C -0.1095(7) 0.748(2) 0.4979(8) 0.0180(4) Uani 0.222(4) 1 d D . P A 2
C6B C -0.1974(9) 0.825(3) 0.4161(10) 0.0241(5) Uani 0.222(4) 1 d D . P A 2
H6B H -0.2088 0.7420 0.3393 0.029 Uiso 0.222(4) 1 calc R U P A 2
C7B C -0.2697(19) 1.021(7) 0.4430(19) 0.0260(7) Uani 0.222(4) 1 d D . P A 2
H7B H -0.3310 1.0733 0.3855 0.031 Uiso 0.222(4) 1 calc R U P A 2
N1B N -0.0378(6) 0.5365(17) 0.4606(6) 0.0213(4) Uani 0.222(4) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.978(4) . ?
C1 C2 1.491(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.395(5) . ?
C2 C7 1.397(5) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 N1 1.427(3) . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.259(4) 3_566 ?
Br1B C1B 1.972(16) . ?
C1B C2B 1.495(14) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.405(14) . ?
C2B C7B 1.409(15) . ?
C3B C4B 1.385(13) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.359(11) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.363(11) . ?
C5B N1B 1.460(12) . ?
C6B C7B 1.373(14) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.232(15) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.6(6) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C7 119.0(4) . . ?
C3 C2 C1 120.2(4) . . ?
C7 C2 C1 120.8(4) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 N1 115.2(2) . . ?
C6 C5 N1 124.8(2) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 N1 C5 114.0(3) 3_566 . ?
C2B C1B Br1B 110(2) . . ?
C2B C1B H1B1 109.7 . . ?
Br1B C1B H1B1 109.7 . . ?
C2B C1B H1B2 109.7 . . ?
Br1B C1B H1B2 109.7 . . ?
H1B1 C1B H1B2 108.2 . . ?
C3B C2B C7B 119.0(15) . . ?
C3B C2B C1B 122.7(16) . . ?
C7B C2B C1B 118.1(16) . . ?
C4B C3B C2B 119.7(13) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C5B C4B C3B 120.0(11) . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 121.2(9) . . ?
C4B C5B N1B 122.1(9) . . ?
C6B C5B N1B 116.7(9) . . ?
C5B C6B C7B 121.0(12) . . ?
C5B C6B H6B 119.5 . . ?
C7B C6B H6B 119.5 . . ?
C6B C7B C2B 119.1(15) . . ?
C6B C7B H7B 120.4 . . ?
C2B C7B H7B 120.4 . . ?
N1B N1B C5B 114.0(10) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -74.2(11) . . . . ?
Br1 C1 C2 C7 106.7(11) . . . . ?
C7 C2 C3 C4 -2.4(15) . . . . ?
C1 C2 C3 C4 178.5(7) . . . . ?
C2 C3 C4 C5 1.7(9) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 N1 -178.8(3) . . . . ?
C4 C5 C6 C7 -2.0(6) . . . . ?
N1 C5 C6 C7 177.3(5) . . . . ?
C5 C6 C7 C2 1.2(11) . . . . ?
C3 C2 C7 C6 1.0(16) . . . . ?
C1 C2 C7 C6 -179.9(8) . . . . ?
C4 C5 N1 N1 -179.1(3) . . . 3_566 ?
C6 C5 N1 N1 1.5(4) . . . 3_566 ?
Br1B C1B C2B C3B -77(4) . . . . ?
Br1B C1B C2B C7B 99(4) . . . . ?
C7B C2B C3B C4B 3(6) . . . . ?
C1B C2B C3B C4B 178(3) . . . . ?
C2B C3B C4B C5B -4(4) . . . . ?
C3B C4B C5B C6B 2.8(19) . . . . ?
C3B C4B C5B N1B -178.0(14) . . . . ?
C4B C5B C6B C7B -1(3) . . . . ?
N1B C5B C6B C7B 180(2) . . . . ?
C5B C6B C7B C2B 0(5) . . . . ?
C3B C2B C7B C6B -1(6) . . . . ?
C1B C2B C7B C6B -177(3) . . . . ?
C4B C5B N1B N1B 4.0(14) . . . 3_566 ?
C6B C5B N1B N1B -176.8(10) . . . 3_566 ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.937
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_12mz154_0m
_database_code_depnum_ccdc_archive 'CCDC 1063378'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   12.9974(15)
_cell_length_b                   4.5160(5)
_cell_length_c                   11.6594(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.481(2)
_cell_angle_gamma                90
_cell_volume                     668.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    3127
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      31.46

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.048
_shelx_estimated_absorpt_T_min   0.136
_shelx_estimated_absorpt_T_max   0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2484
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   SADABS-2008/1
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7535
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.211
_diffrn_reflns_theta_max         31.950
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2184
_reflns_number_gt                1705
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2184
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43600(14) 1.1413(5) 0.65883(17) 0.0419(2) Uani 0.732(4) 1 d D . P A 1
C1 C -0.3461(5) 1.3328(16) 0.5636(5) 0.0367(12) Uani 0.732(4) 1 d D . P A 1
H1A H -0.3881 1.3737 0.4837 0.044 Uiso 0.732(4) 1 calc R U P A 1
H1B H -0.3192 1.5236 0.6000 0.044 Uiso 0.732(4) 1 calc R U P A 1
C2 C -0.2560(7) 1.135(3) 0.5562(7) 0.0274(6) Uani 0.732(4) 1 d D . P A 1
C3 C -0.1725(4) 1.0992(14) 0.6526(5) 0.0278(7) Uani 0.732(4) 1 d D . P A 1
H3 H -0.1722 1.2039 0.7233 0.033 Uiso 0.732(4) 1 calc R U P A 1
C4 C -0.0894(2) 0.9106(6) 0.6455(3) 0.0262(5) Uani 0.732(4) 1 d D . P A 1
H4 H -0.0331 0.8855 0.7119 0.031 Uiso 0.732(4) 1 calc R U P A 1
C5 C -0.0881(2) 0.7590(6) 0.5423(3) 0.0235(5) Uani 0.732(4) 1 d D . P A 1
C6 C -0.1687(3) 0.7991(10) 0.4451(3) 0.0323(8) Uani 0.732(4) 1 d D . P A 1
H6 H -0.1667 0.7018 0.3734 0.039 Uiso 0.732(4) 1 calc R U P A 1
C7 C -0.2534(6) 0.984(2) 0.4527(6) 0.0327(8) Uani 0.732(4) 1 d D . P A 1
H7 H -0.3099 1.0062 0.3863 0.039 Uiso 0.732(4) 1 calc R U P A 1
N1 N 0.00051(19) 0.5662(5) 0.54818(19) 0.0278(4) Uani 0.732(4) 1 d . . P A 1
Br1B Br -0.4226(4) 1.1217(16) 0.6737(5) 0.0419(2) Uani 0.268(4) 1 d D . P A 2
C1B C -0.3330(15) 1.340(5) 0.586(2) 0.0367(12) Uani 0.268(4) 1 d D . P A 2
H1B1 H -0.3772 1.4225 0.5136 0.044 Uiso 0.268(4) 1 calc R U P A 2
H1B2 H -0.2982 1.5062 0.6349 0.044 Uiso 0.268(4) 1 calc R U P A 2
C2B C -0.251(2) 1.140(10) 0.556(2) 0.0274(6) Uani 0.268(4) 1 d D . P A 2
C3B C -0.1605(14) 1.059(4) 0.6389(15) 0.0278(7) Uani 0.268(4) 1 d D . P A 2
H3B H -0.1479 1.1389 0.7161 0.033 Uiso 0.268(4) 1 calc R U P A 2
C4B C -0.0896(8) 0.863(2) 0.6080(9) 0.0262(5) Uani 0.268(4) 1 d D . P A 2
H4B H -0.0273 0.8106 0.6632 0.031 Uiso 0.268(4) 1 calc R U P A 2
C5B C -0.1094(8) 0.747(2) 0.4985(8) 0.0235(5) Uani 0.268(4) 1 d D . P A 2
C6B C -0.1969(10) 0.820(3) 0.4172(11) 0.0323(8) Uani 0.268(4) 1 d D . P A 2
H6B H -0.2082 0.7324 0.3414 0.039 Uiso 0.268(4) 1 calc R U P A 2
C7B C -0.2699(19) 1.017(7) 0.4419(18) 0.0327(8) Uani 0.268(4) 1 d D . P A 2
H7B H -0.3306 1.0697 0.3841 0.039 Uiso 0.268(4) 1 calc R U P A 2
N1B N -0.0375(6) 0.5357(15) 0.4600(6) 0.0278(4) Uani 0.268(4) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.976(5) . ?
C1 C2 1.491(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.393(6) . ?
C2 C7 1.394(5) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(4) . ?
C5 N1 1.434(4) . ?
C6 C7 1.398(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.270(5) 3_566 ?
Br1B C1B 1.968(15) . ?
C1B C2B 1.494(14) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.404(14) . ?
C2B C7B 1.410(14) . ?
C3B C4B 1.380(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.353(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.353(10) . ?
C5B N1B 1.472(12) . ?
C6B C7B 1.378(14) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.237(14) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.7(7) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C7 118.8(5) . . ?
C3 C2 C1 120.5(5) . . ?
C7 C2 C1 120.7(5) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 N1 125.4(3) . . ?
C4 C5 N1 114.7(3) . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 120.9(4) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 N1 C5 112.9(3) 3_566 . ?
C2B C1B Br1B 111(2) . . ?
C2B C1B H1B1 109.5 . . ?
Br1B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
Br1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 108.1 . . ?
C3B C2B C7B 119.7(14) . . ?
C3B C2B C1B 121.8(15) . . ?
C7B C2B C1B 118.5(15) . . ?
C4B C3B C2B 119.7(13) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C5B C4B C3B 119.6(11) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C4B C5B C6B 121.8(10) . . ?
C4B C5B N1B 122.3(9) . . ?
C6B C5B N1B 115.9(9) . . ?
C5B C6B C7B 121.5(12) . . ?
C5B C6B H6B 119.2 . . ?
C7B C6B H6B 119.2 . . ?
C6B C7B C2B 117.8(14) . . ?
C6B C7B H7B 121.1 . . ?
C2B C7B H7B 121.1 . . ?
N1B N1B C5B 112.9(9) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -74.1(14) . . . . ?
Br1 C1 C2 C7 106.4(13) . . . . ?
C7 C2 C3 C4 -1.4(19) . . . . ?
C1 C2 C3 C4 179.1(9) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C3 C4 C5 N1 -178.3(4) . . . . ?
C4 C5 C6 C7 -2.5(8) . . . . ?
N1 C5 C6 C7 177.0(6) . . . . ?
C3 C2 C7 C6 0(2) . . . . ?
C1 C2 C7 C6 179.6(10) . . . . ?
C5 C6 C7 C2 1.9(15) . . . . ?
C6 C5 N1 N1 1.2(5) . . . 3_566 ?
C4 C5 N1 N1 -179.3(3) . . . 3_566 ?
Br1B C1B C2B C3B -78(4) . . . . ?
Br1B C1B C2B C7B 99(4) . . . . ?
C7B C2B C3B C4B 1(5) . . . . ?
C1B C2B C3B C4B 177(3) . . . . ?
C2B C3B C4B C5B -1(3) . . . . ?
C3B C4B C5B C6B 1(2) . . . . ?
C3B C4B C5B N1B -179.6(13) . . . . ?
C4B C5B C6B C7B 0(3) . . . . ?
N1B C5B C6B C7B -179(2) . . . . ?
C5B C6B C7B C2B -1(5) . . . . ?
C3B C2B C7B C6B 0(6) . . . . ?
C1B C2B C7B C6B -176(3) . . . . ?
C4B C5B N1B N1B 4.4(13) . . . 3_566 ?
C6B C5B N1B N1B -175.9(11) . . . 3_566 ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_12mz155_0m
_database_code_depnum_ccdc_archive 'CCDC 1063379'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.0320(11)
_cell_length_b                   4.5311(4)
_cell_length_c                   11.6944(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.4830(10)
_cell_angle_gamma                90
_cell_volume                     674.22(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1294
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.40
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    5.994
_shelx_estimated_absorpt_T_min   0.137
_shelx_estimated_absorpt_T_max   0.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3618
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2008-1'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15300
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         32.027
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2211
_reflns_number_gt                1684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2211
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.4355(2) 1.1381(9) 0.6588(3) 0.0518(3) Uani 0.686(4) 1 d D . P A 1
C1 C -0.3456(7) 1.328(2) 0.5643(9) 0.0459(18) Uani 0.686(4) 1 d D . P A 1
H1A H -0.3875 1.3700 0.4847 0.055 Uiso 0.686(4) 1 calc R U P A 1
H1B H -0.3186 1.5178 0.6008 0.055 Uiso 0.686(4) 1 calc R U P A 1
C2 C -0.2561(9) 1.132(4) 0.5562(9) 0.0340(6) Uani 0.686(4) 1 d D . P A 1
C3 C -0.1716(6) 1.1012(16) 0.6518(6) 0.0332(9) Uani 0.686(4) 1 d D . P A 1
H3 H -0.1701 1.2105 0.7214 0.040 Uiso 0.686(4) 1 calc R U P A 1
C4 C -0.0893(3) 0.9096(9) 0.6449(4) 0.0317(7) Uani 0.686(4) 1 d D . P A 1
H4 H -0.0334 0.8829 0.7112 0.038 Uiso 0.686(4) 1 calc R U P A 1
C5 C -0.0880(3) 0.7588(9) 0.5429(4) 0.0291(7) Uani 0.686(4) 1 d D . P A 1
C6 C -0.1692(5) 0.7973(16) 0.4460(5) 0.0404(12) Uani 0.686(4) 1 d D . P A 1
H6 H -0.1672 0.7006 0.3744 0.048 Uiso 0.686(4) 1 calc R U P A 1
C7 C -0.2539(11) 0.978(4) 0.4538(9) 0.0407(13) Uani 0.686(4) 1 d D . P A 1
H7 H -0.3110 0.9973 0.3882 0.049 Uiso 0.686(4) 1 calc R U P A 1
N1 N 0.0004(3) 0.5650(7) 0.5476(3) 0.0338(6) Uani 0.686(4) 1 d . . P A 1
Br1B Br -0.4208(5) 1.120(2) 0.6744(6) 0.0518(3) Uani 0.314(4) 1 d D . P A 2
C1B C -0.3322(18) 1.332(5) 0.586(2) 0.0459(18) Uani 0.314(4) 1 d D . P A 2
H1B1 H -0.3767 1.4130 0.5128 0.055 Uiso 0.314(4) 1 calc R U P A 2
H1B2 H -0.2971 1.4996 0.6328 0.055 Uiso 0.314(4) 1 calc R U P A 2
C2B C -0.252(2) 1.133(10) 0.555(2) 0.0340(6) Uani 0.314(4) 1 d D . P A 2
C3B C -0.1619(15) 1.048(4) 0.6387(17) 0.0332(9) Uani 0.314(4) 1 d D . P A 2
H3B H -0.1514 1.1189 0.7168 0.040 Uiso 0.314(4) 1 calc R U P A 2
C4B C -0.0894(9) 0.861(2) 0.6075(10) 0.0317(7) Uani 0.314(4) 1 d D . P A 2
H4B H -0.0262 0.8165 0.6623 0.038 Uiso 0.314(4) 1 calc R U P A 2
C5B C -0.1077(9) 0.741(2) 0.4991(9) 0.0291(7) Uani 0.314(4) 1 d D . P A 2
C6B C -0.1962(12) 0.812(4) 0.4164(12) 0.0404(12) Uani 0.314(4) 1 d D . P A 2
H6B H -0.2085 0.7218 0.3414 0.048 Uiso 0.314(4) 1 calc R U P A 2
C7B C -0.268(2) 1.015(9) 0.442(2) 0.0407(13) Uani 0.314(4) 1 d D . P A 2
H7B H -0.3267 1.0731 0.3839 0.049 Uiso 0.314(4) 1 calc R U P A 2
N1B N -0.0379(6) 0.5357(16) 0.4608(6) 0.0338(6) Uani 0.314(4) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.974(7) . ?
C1 C2 1.485(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.391(7) . ?
C2 C3 1.396(7) . ?
C3 C4 1.396(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 N1 1.440(5) . ?
C6 C7 1.395(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.258(6) 3_566 ?
Br1B C1B 1.964(15) . ?
C1B C2B 1.486(13) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C7B 1.400(13) . ?
C2B C3B 1.404(13) . ?
C3B C4B 1.374(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.353(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.373(11) . ?
C5B N1B 1.439(13) . ?
C6B C7B 1.387(14) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.236(15) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.1(8) . . ?
C2 C1 H1A 109.6 . . ?
Br1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
Br1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 118.7(6) . . ?
C7 C2 C1 121.1(7) . . ?
C3 C2 C1 120.2(7) . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 N1 115.3(4) . . ?
C6 C5 N1 124.9(4) . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 121.0(6) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 N1 C5 113.5(4) 3_566 . ?
C2B C1B Br1B 110.7(19) . . ?
C2B C1B H1B1 109.5 . . ?
Br1B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
Br1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 108.1 . . ?
C7B C2B C3B 118.9(14) . . ?
C7B C2B C1B 119.2(16) . . ?
C3B C2B C1B 121.8(16) . . ?
C4B C3B C2B 120.1(13) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C5B C4B C3B 120.3(12) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C4B C5B C6B 121.1(11) . . ?
C4B C5B N1B 123.8(10) . . ?
C6B C5B N1B 115.1(11) . . ?
C5B C6B C7B 120.2(13) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B C2B 119.2(15) . . ?
C6B C7B H7B 120.4 . . ?
C2B C7B H7B 120.4 . . ?
N1B N1B C5B 113.3(10) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 105.3(19) . . . . ?
Br1 C1 C2 C3 -75.5(17) . . . . ?
C7 C2 C3 C4 -3(2) . . . . ?
C1 C2 C3 C4 178.1(11) . . . . ?
C2 C3 C4 C5 2.7(15) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C3 C4 C5 N1 -179.1(6) . . . . ?
C4 C5 C6 C7 -2.8(13) . . . . ?
N1 C5 C6 C7 176.3(11) . . . . ?
C3 C2 C7 C6 0(3) . . . . ?
C1 C2 C7 C6 179.2(15) . . . . ?
C5 C6 C7 C2 3(2) . . . . ?
C4 C5 N1 N1 -178.9(4) . . . 3_566 ?
C6 C5 N1 N1 1.9(7) . . . 3_566 ?
Br1B C1B C2B C7B 101(4) . . . . ?
Br1B C1B C2B C3B -76(4) . . . . ?
C7B C2B C3B C4B 3(6) . . . . ?
C1B C2B C3B C4B 180(3) . . . . ?
C2B C3B C4B C5B -5(4) . . . . ?
C3B C4B C5B C6B 3(2) . . . . ?
C3B C4B C5B N1B -177.6(15) . . . . ?
C4B C5B C6B C7B 1(3) . . . . ?
N1B C5B C6B C7B -178(3) . . . . ?
C5B C6B C7B C2B -4(6) . . . . ?
C3B C2B C7B C6B 2(7) . . . . ?
C1B C2B C7B C6B -175(3) . . . . ?
C4B C5B N1B N1B 4.3(15) . . . 3_566 ?
C6B C5B N1B N1B -176.2(13) . . . 3_566 ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_12mz156_0m
_database_code_depnum_ccdc_archive 'CCDC 1063380'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.061(3)
_cell_length_b                   4.5482(9)
_cell_length_c                   11.736(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.463(3)
_cell_angle_gamma                90
_cell_volume                     680.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    340(2)
_cell_measurement_reflns_used    2343
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      30.26

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    5.937
_shelx_estimated_absorpt_T_min   0.139
_shelx_estimated_absorpt_T_max   0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2553
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS-2008/1

_diffrn_ambient_temperature      340(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7724
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.195
_diffrn_reflns_theta_max         31.913
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2224
_reflns_number_gt                1373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2224
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.4355(2) 1.1344(11) 0.6589(4) 0.0636(4) Uani 0.645(5) 1 d D . P A 1
C1 C -0.3462(8) 1.323(3) 0.5646(10) 0.054(2) Uani 0.645(5) 1 d D . P A 1
H1A H -0.3880 1.3623 0.4851 0.065 Uiso 0.645(5) 1 calc R U P A 1
H1B H -0.3199 1.5133 0.6003 0.065 Uiso 0.645(5) 1 calc R U P A 1
C2 C -0.2559(10) 1.128(5) 0.5576(11) 0.0411(7) Uani 0.645(5) 1 d D . P A 1
C3 C -0.1712(7) 1.099(2) 0.6514(8) 0.0394(10) Uani 0.645(5) 1 d D . P A 1
H3 H -0.1693 1.2091 0.7207 0.047 Uiso 0.645(5) 1 calc R U P A 1
C4 C -0.0890(4) 0.9100(12) 0.6443(4) 0.0381(9) Uani 0.645(5) 1 d D . P A 1
H4 H -0.0327 0.8857 0.7100 0.046 Uiso 0.645(5) 1 calc R U P A 1
C5 C -0.0886(4) 0.7581(11) 0.5434(4) 0.0341(10) Uani 0.645(5) 1 d D . P A 1
C6 C -0.1693(7) 0.799(3) 0.4478(6) 0.0497(16) Uani 0.645(5) 1 d D . P A 1
H6 H -0.1670 0.7053 0.3760 0.060 Uiso 0.645(5) 1 calc R U P A 1
C7 C -0.2541(15) 0.976(5) 0.4558(11) 0.0494(17) Uani 0.645(5) 1 d D . P A 1
H7 H -0.3114 0.9929 0.3908 0.059 Uiso 0.645(5) 1 calc R U P A 1
N1 N 0.0005(3) 0.5656(8) 0.5472(3) 0.0417(7) Uani 0.645(5) 1 d . . P A 1
Br1B Br -0.4186(5) 1.119(2) 0.6745(7) 0.0636(4) Uani 0.355(5) 1 d D . P A 2
C1B C -0.3297(16) 1.329(5) 0.586(2) 0.054(2) Uani 0.355(5) 1 d D . P A 2
H1B1 H -0.3740 1.4144 0.5150 0.065 Uiso 0.355(5) 1 calc R U P A 2
H1B2 H -0.2931 1.4921 0.6344 0.065 Uiso 0.355(5) 1 calc R U P A 2
C2B C -0.2509(19) 1.126(9) 0.554(2) 0.0411(7) Uani 0.355(5) 1 d D . P A 2
C3B C -0.1623(15) 1.043(4) 0.6373(17) 0.0394(10) Uani 0.355(5) 1 d D . P A 2
H3B H -0.1525 1.1140 0.7150 0.047 Uiso 0.355(5) 1 calc R U P A 2
C4B C -0.0894(9) 0.859(2) 0.6068(10) 0.0381(9) Uani 0.355(5) 1 d D . P A 2
H4B H -0.0266 0.8144 0.6618 0.046 Uiso 0.355(5) 1 calc R U P A 2
C5B C -0.1067(10) 0.740(2) 0.4988(9) 0.0341(10) Uani 0.355(5) 1 d D . P A 2
C6B C -0.1944(15) 0.806(5) 0.4170(13) 0.0497(16) Uani 0.355(5) 1 d D . P A 2
H6B H -0.2065 0.7136 0.3426 0.060 Uiso 0.355(5) 1 calc R U P A 2
C7B C -0.267(3) 1.008(10) 0.442(2) 0.0494(17) Uani 0.355(5) 1 d D . P A 2
H7B H -0.3256 1.0640 0.3835 0.059 Uiso 0.355(5) 1 calc R U P A 2
N1B N -0.0379(6) 0.5327(15) 0.4607(7) 0.0417(7) Uani 0.355(5) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.970(7) . ?
C1 C2 1.491(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.386(7) . ?
C2 C3 1.389(8) . ?
C3 C4 1.392(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(6) . ?
C5 N1 1.449(7) . ?
C6 C7 1.389(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.256(8) 3_566 ?
Br1B C1B 1.962(14) . ?
C1B C2B 1.492(12) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C7B 1.393(13) . ?
C2B C3B 1.398(13) . ?
C3B C4B 1.372(11) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.352(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.360(12) . ?
C5B N1B 1.437(13) . ?
C6B C7B 1.392(13) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.235(17) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 110.1(9) . . ?
C2 C1 H1A 109.6 . . ?
Br1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
Br1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 118.5(7) . . ?
C7 C2 C1 120.4(8) . . ?
C3 C2 C1 121.2(8) . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 N1 115.5(4) . . ?
C6 C5 N1 125.1(5) . . ?
C5 C6 C7 120.3(6) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.7(8) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 N1 C5 113.9(5) 3_566 . ?
C2B C1B Br1B 110.7(18) . . ?
C2B C1B H1B1 109.5 . . ?
Br1B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
Br1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 108.1 . . ?
C7B C2B C3B 119.1(14) . . ?
C7B C2B C1B 120.8(15) . . ?
C3B C2B C1B 120.0(15) . . ?
C4B C3B C2B 119.9(13) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C5B C4B C3B 120.3(12) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4B C5B C6B 121.2(11) . . ?
C4B C5B N1B 124.4(10) . . ?
C6B C5B N1B 114.4(12) . . ?
C5B C6B C7B 120.2(14) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B C2B 119.0(15) . . ?
C6B C7B H7B 120.5 . . ?
C2B C7B H7B 120.5 . . ?
N1B N1B C5B 112.4(10) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C7 105(2) . . . . ?
Br1 C1 C2 C3 -76(2) . . . . ?
C7 C2 C3 C4 -3(3) . . . . ?
C1 C2 C3 C4 178.2(13) . . . . ?
C2 C3 C4 C5 2.5(18) . . . . ?
C3 C4 C5 C6 1.3(12) . . . . ?
C3 C4 C5 N1 -179.4(7) . . . . ?
C4 C5 C6 C7 -4(2) . . . . ?
N1 C5 C6 C7 176.3(16) . . . . ?
C3 C2 C7 C6 0(4) . . . . ?
C1 C2 C7 C6 178.7(19) . . . . ?
C5 C6 C7 C2 4(3) . . . . ?
C4 C5 N1 N1 -178.7(5) . . . 3_566 ?
C6 C5 N1 N1 0.6(10) . . . 3_566 ?
Br1B C1B C2B C7B 100(4) . . . . ?
Br1B C1B C2B C3B -77(4) . . . . ?
C7B C2B C3B C4B 3(6) . . . . ?
C1B C2B C3B C4B -179(2) . . . . ?
C2B C3B C4B C5B -5(4) . . . . ?
C3B C4B C5B C6B 2(3) . . . . ?
C3B C4B C5B N1B -176.6(15) . . . . ?
C4B C5B C6B C7B 3(4) . . . . ?
N1B C5B C6B C7B -179(3) . . . . ?
C5B C6B C7B C2B -4(7) . . . . ?
C3B C2B C7B C6B 1(7) . . . . ?
C1B C2B C7B C6B -176(4) . . . . ?
C4B C5B N1B N1B 2.2(16) . . . 3_566 ?
C6B C5B N1B N1B -176.5(16) . . . 3_566 ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_12mz157_0m
_database_code_depnum_ccdc_archive 'CCDC 1063381'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 (1E)-1,2-bis[4-(Bromomethyl)phenyl]-diazene
;
_chemical_name_common            ?
_chemical_melting_point          492-498K
_chemical_formula_moiety         'C14 H12 Br2 N2'
_chemical_formula_sum            'C14 H12 Br2 N2'
_chemical_formula_weight         368.08

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

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

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

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

_cell_length_a                   13.097(4)
_cell_length_b                   4.5652(15)
_cell_length_c                   11.779(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.471(5)
_cell_angle_gamma                90
_cell_volume                     687.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    375(2)
_cell_measurement_reflns_used    4850
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      31.18

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    5.877
_shelx_estimated_absorpt_T_min   0.140
_shelx_estimated_absorpt_T_max   0.435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2729
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS-2008/1
_diffrn_ambient_temperature      375(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart 1000 area detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15439
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.186
_diffrn_reflns_theta_max         31.785
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2239
_reflns_number_gt                1472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.2622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     110
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.4276(3) 1.1020(7) 0.6685(3) 0.0671(5) Uani 0.632(5) 1 d D . P A 1
C1 C -0.3465(9) 1.311(3) 0.5700(14) 0.060(2) Uani 0.632(5) 1 d D . P A 1
H1A H -0.3912 1.3454 0.4919 0.071 Uiso 0.632(5) 1 calc R U P A 1
H1B H -0.3233 1.5031 0.6050 0.071 Uiso 0.632(5) 1 calc R U P A 1
C2 C -0.2534(11) 1.132(5) 0.5591(12) 0.0453(11) Uani 0.632(5) 1 d D . P A 1
C3 C -0.1702(9) 1.093(3) 0.6527(8) 0.0444(12) Uani 0.632(5) 1 d D . P A 1
H3 H -0.1692 1.1939 0.7235 0.053 Uiso 0.632(5) 1 calc R U P A 1
C4 C -0.0885(5) 0.9091(14) 0.6438(5) 0.0420(11) Uani 0.632(5) 1 d D . P A 1
H4 H -0.0314 0.8866 0.7084 0.050 Uiso 0.632(5) 1 calc R U P A 1
C5 C -0.0887(5) 0.7582(14) 0.5430(5) 0.0380(12) Uani 0.632(5) 1 d D . P A 1
C6 C -0.1696(8) 0.798(3) 0.4478(7) 0.0552(19) Uani 0.632(5) 1 d D . P A 1
H6 H -0.1681 0.7046 0.3760 0.066 Uiso 0.632(5) 1 calc R U P A 1
C7 C -0.2534(14) 0.974(5) 0.4579(11) 0.0537(18) Uani 0.632(5) 1 d D . P A 1
H7 H -0.3120 0.9881 0.3945 0.064 Uiso 0.632(5) 1 calc R U P A 1
N1 N 0.0009(3) 0.5649(9) 0.5467(4) 0.0451(8) Uani 0.632(5) 1 d . . P A 1
Br1B Br -0.4308(5) 1.1720(10) 0.6580(6) 0.0671(5) Uani 0.368(5) 1 d D . P A 2
C1B C -0.3275(18) 1.345(5) 0.578(3) 0.060(2) Uani 0.368(5) 1 d D . P A 2
H1B1 H -0.3641 1.4374 0.5044 0.071 Uiso 0.368(5) 1 calc R U P A 2
H1B2 H -0.2869 1.4981 0.6275 0.071 Uiso 0.368(5) 1 calc R U P A 2
C2B C -0.2548(19) 1.113(10) 0.552(2) 0.0453(11) Uani 0.368(5) 1 d D . P A 2
C3B C -0.1633(17) 1.049(5) 0.6333(17) 0.0444(12) Uani 0.368(5) 1 d D . P A 2
H3B H -0.1511 1.1373 0.7080 0.053 Uiso 0.368(5) 1 calc R U P A 2
C4B C -0.0899(10) 0.858(3) 0.6064(10) 0.0420(11) Uani 0.368(5) 1 d D . P A 2
H4B H -0.0286 0.8116 0.6630 0.050 Uiso 0.368(5) 1 calc R U P A 2
C5B C -0.1061(11) 0.737(3) 0.4990(9) 0.0380(12) Uani 0.368(5) 1 d D . P A 2
C6B C -0.1947(17) 0.800(6) 0.4173(15) 0.0552(19) Uani 0.368(5) 1 d D . P A 2
H6B H -0.2063 0.7048 0.3439 0.066 Uiso 0.368(5) 1 calc R U P A 2
C7B C -0.268(3) 1.002(10) 0.439(2) 0.0537(18) Uani 0.368(5) 1 d D . P A 2
H7B H -0.3255 1.0614 0.3793 0.064 Uiso 0.368(5) 1 calc R U P A 2
N1B N -0.0380(7) 0.5363(16) 0.4618(7) 0.0451(8) Uani 0.368(5) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.980(8) . ?
C1 C2 1.494(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.385(8) . ?
C2 C7 1.393(8) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(7) . ?
C5 N1 1.461(8) . ?
C6 C7 1.388(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 N1 1.246(9) 3_566 ?
Br1B C1B 1.974(13) . ?
C1B C2B 1.497(14) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.391(13) . ?
C2B C7B 1.403(13) . ?
C3B C4B 1.385(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.355(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.369(12) . ?
C5B N1B 1.411(15) . ?
C6B C7B 1.396(14) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
N1B N1B 1.235(18) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 109.8(10) . . ?
C2 C1 H1A 109.7 . . ?
Br1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
Br1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C7 118.0(8) . . ?
C3 C2 C1 121.2(9) . . ?
C7 C2 C1 120.4(9) . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 N1 115.2(5) . . ?
C6 C5 N1 125.1(6) . . ?
C5 C6 C7 119.3(7) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 121.4(8) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
N1 N1 C5 113.5(6) 3_566 . ?
C2B C1B Br1B 110.2(18) . . ?
C2B C1B H1B1 109.6 . . ?
Br1B C1B H1B1 109.6 . . ?
C2B C1B H1B2 109.6 . . ?
Br1B C1B H1B2 109.6 . . ?
H1B1 C1B H1B2 108.1 . . ?
C3B C2B C7B 119.3(13) . . ?
C3B C2B C1B 120.1(17) . . ?
C7B C2B C1B 119.4(16) . . ?
C4B C3B C2B 120.9(13) . . ?
C4B C3B H3B 119.6 . . ?
C2B C3B H3B 119.6 . . ?
C5B C4B C3B 119.6(12) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C4B C5B C6B 120.5(12) . . ?
C4B C5B N1B 124.9(11) . . ?
C6B C5B N1B 114.6(12) . . ?
C5B C6B C7B 121.7(14) . . ?
C5B C6B H6B 119.2 . . ?
C7B C6B H6B 119.2 . . ?
C6B C7B C2B 117.5(15) . . ?
C6B C7B H7B 121.2 . . ?
C2B C7B H7B 121.2 . . ?
N1B N1B C5B 114.4(10) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -70(2) . . . . ?
Br1 C1 C2 C7 103(2) . . . . ?
C7 C2 C3 C4 2(3) . . . . ?
C1 C2 C3 C4 174.9(15) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 C6 2.1(15) . . . . ?
C3 C4 C5 N1 -178.3(9) . . . . ?
C4 C5 C6 C7 -4(2) . . . . ?
N1 C5 C6 C7 176.1(16) . . . . ?
C5 C6 C7 C2 5(4) . . . . ?
C3 C2 C7 C6 -4(4) . . . . ?
C1 C2 C7 C6 -177(2) . . . . ?
C4 C5 N1 N1 -178.9(6) . . . 3_566 ?
C6 C5 N1 N1 0.7(12) . . . 3_566 ?
Br1B C1B C2B C3B -90(4) . . . . ?
Br1B C1B C2B C7B 103(4) . . . . ?
C7B C2B C3B C4B -6(6) . . . . ?
C1B C2B C3B C4B -173(3) . . . . ?
C2B C3B C4B C5B 2(4) . . . . ?
C3B C4B C5B C6B 0(3) . . . . ?
C3B C4B C5B N1B -179.1(17) . . . . ?
C4B C5B C6B C7B 3(5) . . . . ?
N1B C5B C6B C7B -178(3) . . . . ?
C5B C6B C7B C2B -7(7) . . . . ?
C3B C2B C7B C6B 8(7) . . . . ?
C1B C2B C7B C6B 176(4) . . . . ?
C4B C5B N1B N1B 3.5(18) . . . 3_566 ?
C6B C5B N1B N1B -175.2(18) . . . 3_566 ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.095

