#------------------------------------------------------------------------------
#$Date: 2018-11-22 05:47:53 +0200 (Thu, 22 Nov 2018) $
#$Revision: 212108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021363.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021363
loop_
_publ_author_name
'Vande Velde, Christophe M. L.'
'Zeller, Matthias'
'Azov, Vladimir A.'
_publ_section_title
;
 Comparison of computationally cheap methods for providing insight into
 the crystal packing of highly bromomethylated azobenzenes
;
_journal_coeditor_code           KY3150
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618015309
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C14 H10 Br4 N2'
_chemical_formula_moiety         'C14 H10 Br4 N2'
_chemical_formula_sum            'C14 H10 Br4 N2'
_chemical_formula_weight         525.88
_chemical_melting_point          425.1(10)
_chemical_name_systematic
;
(E)-1,2-Bis[4-(dibromomethyl)phenyl]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_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_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 114.797(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.379(3)
_cell_length_b                   8.6401(10)
_cell_length_c                   9.8451(10)
_cell_measurement_reflns_used    2626
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.86
_cell_measurement_theta_min      2.41
_cell_volume                     1573.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and
shelXle(Hübschle et al., 2011)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5663
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.241
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    10.220
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.602
_refine_ls_extinction_coef       0.00183(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0249P)²+1.3279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0556
_reflns_number_gt                2049
_reflns_number_total             2322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3150sup1.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '151-153 C' was changed to
'425.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               2021363
_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.
;
_shelx_estimated_absorpt_t_min   0.078
_shelx_estimated_absorpt_t_max   0.112
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.23156(2) 0.44833(3) 0.27413(3) 0.01427(7) Uani d 1
Br Br2 0.36677(2) 0.26407(2) 0.50812(3) 0.01505(8) Uani d 1
N N1 0.48068(10) 0.9973(2) 0.5356(2) 0.0120(4) Uani d 1
C C1 0.44107(11) 0.8564(2) 0.5167(2) 0.0096(4) Uani d 1
C C2 0.44206(13) 0.7356(2) 0.4222(3) 0.0124(4) Uani d 1
H H2 0.470686 0.743489 0.367280 0.015 Uiso calc 1
C C3 0.40098(13) 0.6056(2) 0.4103(3) 0.0124(4) Uani d 1
H H3 0.401720 0.522915 0.347309 0.015 Uiso calc 1
C C4 0.35791(12) 0.5935(2) 0.4902(2) 0.0102(4) Uani d 1
C C5 0.35691(12) 0.7138(2) 0.5828(3) 0.0116(4) Uani d 1
H H5 0.327697 0.706657 0.636582 0.014 Uiso calc 1
C C6 0.39902(12) 0.8452(2) 0.5966(3) 0.0119(4) Uani d 1
H H6 0.398937 0.927179 0.660821 0.014 Uiso calc 1
C C7 0.31141(13) 0.4548(2) 0.4738(3) 0.0118(4) Uani d 1
H H7 0.290721 0.461829 0.549495 0.014 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
N1 N1 C1 5_676 114.3(2)
C6 C1 C2 . 120.49(19)
C6 C1 N1 . 115.77(18)
C2 C1 N1 . 123.7(2)
C3 C2 C1 . 119.1(2)
C3 C2 H2 . 120.5
C1 C2 H2 . 120.5
C2 C3 C4 . 120.8(2)
C2 C3 H3 . 119.6
C4 C3 H3 . 119.6
C5 C4 C3 . 119.76(19)
C5 C4 C7 . 119.2(2)
C3 C4 C7 . 120.99(19)
C4 C5 C6 . 119.7(2)
C4 C5 H5 . 120.2
C6 C5 H5 . 120.2
C1 C6 C5 . 120.2(2)
C1 C6 H6 . 119.9
C5 C6 H6 . 119.9
C4 C7 Br2 . 111.44(16)
C4 C7 Br1 . 110.73(15)
Br2 C7 Br1 . 109.11(10)
C4 C7 H7 . 108.5
Br2 C7 H7 . 108.5
Br1 C7 H7 . 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C7 . 1.958(2)
Br2 C7 . 1.945(2)
N1 N1 5_676 1.255(4)
N1 C1 . 1.429(3)
C1 C6 . 1.389(3)
C1 C2 . 1.404(3)
C2 C3 . 1.376(3)
C2 H2 . 0.9500
C3 C4 . 1.407(3)
C3 H3 . 0.9500
C4 C5 . 1.388(3)
C4 C7 . 1.494(3)
C5 C6 . 1.395(3)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 H7 . 1.0000
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_site_symmetry_1
_geom_torsion
N1 N1 C1 C6 5_676 178.6(2)
N1 N1 C1 C2 5_676 -2.6(4)
C6 C1 C2 C3 . -0.2(3)
N1 C1 C2 C3 . -179.0(2)
C1 C2 C3 C4 . 0.6(3)
C2 C3 C4 C5 . -0.3(3)
C2 C3 C4 C7 . 178.0(2)
C3 C4 C5 C6 . -0.4(3)
C7 C4 C5 C6 . -178.7(2)
C2 C1 C6 C5 . -0.4(3)
N1 C1 C6 C5 . 178.4(2)
C4 C5 C6 C1 . 0.8(3)
C5 C4 C7 Br2 . -128.80(19)
C3 C4 C7 Br2 . 52.9(3)
C5 C4 C7 Br1 . 109.6(2)
C3 C4 C7 Br1 . -68.7(2)

_cod_database_fobs_code 2021363
