#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:14:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179620 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/84/4508441.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4508441
loop_
_publ_author_name
'Karanam, Maheswararao'
'Choudhury, Angshuman Roy'
_publ_section_title
;
 Study of Halogen-Mediated Weak Interactions in a Series of
 Halogen-Substituted Azobenzenes
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4803
_journal_paper_doi               10.1021/cg400967k
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C12 H8 Br2 N2'
_chemical_formula_sum            'C12 H8 Br2 N2'
_chemical_formula_weight         340.02
_chemical_name_systematic
;
 (E)-bis(2-bromophenyl)diazene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-18T17:35:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.101(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7149(10)
_cell_length_b                   3.9697(2)
_cell_length_c                   13.7591(7)
_cell_measurement_reflns_used    2800
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.797
_cell_measurement_theta_min      2.771
_cell_volume                     1145.10(10)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3865
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.05
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.3127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.1174 before and 0.0338 after correction.
        The Ratio of minimum to maximum transmission is 0.4192.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²+1.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0613
_reflns_number_gt                948
_reflns_number_total             1016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400967k_si_002.cif
_cod_data_source_block           az04_100k_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C12/c1
_cod_database_code               4508441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.40541(13) 0.9384(6) 0.3428(2) 0.0196(5) Uani 1 1 d .
H1 H 0.4345 0.9808 0.3032 0.023 Uiso 1 1 calc R
C2 C 0.34176(13) 1.0253(5) 0.3060(2) 0.0207(6) Uani 1 1 d .
H2 H 0.3273 1.1263 0.2415 0.025 Uiso 1 1 calc R
C3 C 0.29909(13) 0.9644(5) 0.3638(2) 0.0191(5) Uani 1 1 d .
H3 H 0.2556 1.027 0.3391 0.023 Uiso 1 1 calc R
C4 C 0.31994(11) 0.8117(5) 0.45819(17) 0.0169(5) Uani 1 1 d .
C5 C 0.38426(11) 0.7285(5) 0.49394(16) 0.0170(5) Uani 1 1 d .
C6 C 0.42702(11) 0.7905(6) 0.43663(17) 0.0187(5) Uani 1 1 d .
H6 H 0.4707 0.732 0.4616 0.022 Uiso 1 1 calc R
N1 N 0.27903(9) 0.7446(5) 0.52248(14) 0.0190(4) Uani 1 1 d .
Br1 Br 0.415261(11) 0.52346(6) 0.622213(16) 0.01975(14) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0235(13) 0.0181(11) 0.0192(13) -0.0024(10) 0.0094(10) -0.0032(9)
C2 0.0255(14) 0.0191(12) 0.0178(14) 0.0006(9) 0.0061(11) -0.0028(9)
C3 0.0188(13) 0.0191(12) 0.0183(13) -0.0001(9) 0.0028(10) -0.0008(9)
C4 0.0210(11) 0.0128(11) 0.0173(11) -0.0026(8) 0.0057(9) -0.0032(9)
C5 0.0231(12) 0.0148(11) 0.0126(11) -0.0021(8) 0.0035(9) -0.0004(8)
C6 0.0186(12) 0.0167(11) 0.0215(12) -0.0033(9) 0.0062(10) -0.0001(9)
N1 0.0189(9) 0.0184(10) 0.0200(10) -0.0009(8) 0.0059(8) -0.0004(8)
Br1 0.0226(2) 0.02047(18) 0.0164(2) 0.00161(8) 0.00557(13) 0.00409(8)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 H1 119.7 .
C6 C1 H1 119.7 .
C6 C1 C2 120.6(2) .
C1 C2 H2 120.1 .
C1 C2 C3 119.9(2) .
C3 C2 H2 120.1 .
C2 C3 H3 119.9 .
C2 C3 C4 120.3(2) .
C4 C3 H3 119.9 .
C3 C4 N1 123.5(2) .
C5 C4 C3 118.9(2) .
C5 C4 N1 117.6(2) .
C4 C5 Br1 120.60(17) .
C6 C5 C4 121.0(2) .
C6 C5 Br1 118.44(17) .
C1 C6 C5 119.4(2) .
C1 C6 H6 120.3 .
C5 C6 H6 120.3 .
N1 N1 C4 113.3(2) 7_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.95 .
C1 C2 1.386(4) .
C1 C6 1.385(4) .
C2 H2 0.95 .
C2 C3 1.390(4) .
C3 H3 0.95 .
C3 C4 1.397(3) .
C4 C5 1.394(3) .
C4 N1 1.432(3) .
C5 C6 1.388(3) .
C5 Br1 1.900(2) .
C6 H6 0.95 .
N1 N1 1.252(4) 7_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_4
C1 C2 C3 C4 -0.9(3) .
C2 C1 C6 C5 0.2(4) .
C2 C3 C4 C5 1.3(3) .
C2 C3 C4 N1 179.2(2) .
C3 C4 C5 C6 -1.0(3) .
C3 C4 C5 Br1 179.51(16) .
C3 C4 N1 N1 17.0(4) 7_566
C4 C5 C6 C1 0.3(3) .
C5 C4 N1 N1 -165.1(2) 7_566
C6 C1 C2 C3 0.1(4) .
N1 C4 C5 C6 -179.0(2) .
N1 C4 C5 Br1 1.5(3) .
Br1 C5 C6 C1 179.75(17) .
