#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/36/2233630.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_2233630
loop_
_publ_author_name
'Novina, J. Josephine'
'Vasuki, G.'
'Kumar, Sushil'
'Thomas, K. R. Justin'
_publ_section_title
;
 4,4'-Dibromo-2-nitrobiphenyl
;
_journal_coeditor_code           SU2358
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o319
_journal_paper_doi               10.1107/S1600536812000347
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H7 Br2 N O2'
_chemical_formula_moiety         'C12 H7 Br2 N O2'
_chemical_formula_sum            'C12 H7 Br2 N O2'
_chemical_formula_weight         357.01
_chemical_name_systematic
;
4,4'-Dibromo-2-nitrobiphenyl
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.8761(14)
_cell_length_b                   7.4350(7)
_cell_length_c                   20.7517(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     2449.5(4)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13009
_diffrn_reflns_theta_full        26.95
_diffrn_reflns_theta_max         26.95
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    6.606
_exptl_absorpt_correction_T_max  0.138
_exptl_absorpt_correction_T_min  0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.698
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+1.6705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                1521
_reflns_number_total             2607
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2358.cif
_cod_data_source_block           I
_cod_database_code               2233630
_cod_database_fobs_code          2233630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.03710(3) 0.09619(7) 0.65877(2) 0.05528(18) Uani d . 1 1
Br Br2 0.15585(3) 0.40559(8) 0.15916(2) 0.06048(19) Uani d . 1 1
C C7 0.1445(2) 0.3592(6) 0.24826(17) 0.0382(10) Uani d . 1 1
C C9 0.1668(2) 0.1683(6) 0.33822(18) 0.0410(10) Uani d . 1 1
H H9 0.1880 0.0618 0.3552 0.049 Uiso calc R 1 1
C C1 0.0668(2) 0.1609(5) 0.57419(16) 0.0321(9) Uani d . 1 1
O O1 0.30721(17) 0.1125(4) 0.51041(14) 0.0524(8) Uani d . 1 1
C C11 0.0974(3) 0.4456(6) 0.35168(19) 0.0438(11) Uani d . 1 1
H H11 0.0702 0.5287 0.3779 0.053 Uiso calc R 1 1
N N 0.26111(19) 0.2075(5) 0.47864(15) 0.0342(8) Uani d . 1 1
C C5 0.0275(2) 0.2556(5) 0.46893(18) 0.0343(10) Uani d . 1 1
H H5 -0.0144 0.2906 0.4403 0.041 Uiso calc R 1 1
O O2 0.28561(16) 0.3083(5) 0.43688(14) 0.0518(8) Uani d . 1 1
C C4 0.1106(2) 0.2495(5) 0.44718(16) 0.0289(9) Uani d . 1 1
C C2 0.1493(2) 0.1555(5) 0.55524(17) 0.0329(9) Uani d . 1 1
H H2 0.1910 0.1212 0.5842 0.039 Uiso calc R 1 1
C C10 0.1272(2) 0.2897(5) 0.37828(16) 0.0292(9) Uani d . 1 1
C C6 0.0050(2) 0.2116(5) 0.53120(17) 0.0362(10) Uani d . 1 1
H H6 -0.0511 0.2162 0.5440 0.043 Uiso calc R 1 1
C C8 0.1752(2) 0.2031(7) 0.27314(19) 0.0467(12) Uani d . 1 1
H H8 0.2018 0.1201 0.2465 0.056 Uiso calc R 1 1
C C3 0.1701(2) 0.2011(5) 0.49318(17) 0.0280(9) Uani d . 1 1
C C12 0.1067(3) 0.4826(6) 0.28703(19) 0.0476(11) Uani d . 1 1
H H12 0.0873 0.5908 0.2701 0.057 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0631(3) 0.0675(4) 0.0352(3) -0.0030(3) 0.01363(19) 0.0059(2)
Br2 0.0541(3) 0.0981(5) 0.0293(2) 0.0006(3) 0.00445(18) 0.0110(3)
C7 0.034(2) 0.056(3) 0.025(2) -0.002(2) -0.0014(17) 0.002(2)
C9 0.046(3) 0.042(3) 0.034(2) 0.011(2) 0.0008(17) 0.003(2)
C1 0.035(2) 0.036(3) 0.0254(19) -0.0034(18) 0.0028(16) -0.0055(18)
O1 0.0363(16) 0.074(2) 0.0470(19) 0.0164(17) -0.0024(13) 0.0104(17)
C11 0.054(3) 0.045(3) 0.033(2) 0.015(2) 0.0106(18) 0.001(2)
N 0.0308(18) 0.042(2) 0.0297(18) -0.0003(17) -0.0018(14) -0.0033(17)
C5 0.032(2) 0.039(3) 0.031(2) 0.0032(19) -0.0054(15) -0.0030(19)
O2 0.0366(18) 0.066(2) 0.0530(19) -0.0062(15) 0.0047(13) 0.0157(18)
C4 0.031(2) 0.029(2) 0.027(2) 0.0010(17) -0.0027(15) -0.0020(17)
C2 0.031(2) 0.037(3) 0.030(2) 0.0020(18) -0.0052(16) -0.0032(18)
C10 0.029(2) 0.035(3) 0.0239(18) 0.0014(18) -0.0032(15) -0.0006(19)
C6 0.028(2) 0.040(3) 0.040(2) 0.0018(19) 0.0046(17) -0.005(2)
C8 0.049(3) 0.059(3) 0.032(2) 0.010(2) 0.0054(17) -0.012(2)
C3 0.024(2) 0.032(2) 0.029(2) 0.0016(17) 0.0005(13) -0.0016(18)
C12 0.057(3) 0.049(3) 0.037(2) 0.012(2) 0.0012(19) 0.013(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C7 C12 120.6(4)
C8 C7 Br2 119.5(3)
C12 C7 Br2 119.8(3)
C10 C9 C8 120.7(4)
C10 C9 H9 119.6
C8 C9 H9 119.6
C2 C1 C6 120.3(3)
C2 C1 Br1 120.1(3)
C6 C1 Br1 119.7(3)
C10 C11 C12 121.7(4)
C10 C11 H11 119.2
C12 C11 H11 119.2
O2 N O1 123.8(3)
O2 N C3 118.7(3)
O1 N C3 117.5(3)
C6 C5 C4 122.7(3)
C6 C5 H5 118.6
C4 C5 H5 118.6
C3 C4 C5 115.4(3)
C3 C4 C10 126.4(3)
C5 C4 C10 118.2(3)
C1 C2 C3 119.5(3)
C1 C2 H2 120.2
C3 C2 H2 120.2
C11 C10 C9 118.0(3)
C11 C10 C4 119.8(3)
C9 C10 C4 122.0(4)
C1 C6 C5 119.0(3)
C1 C6 H6 120.5
C5 C6 H6 120.5
C7 C8 C9 119.7(4)
C7 C8 H8 120.1
C9 C8 H8 120.1
C2 C3 C4 123.1(3)
C2 C3 N 115.8(3)
C4 C3 N 121.1(3)
C7 C12 C11 119.2(4)
C7 C12 H12 120.4
C11 C12 H12 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.880(3)
Br2 C7 1.890(4)
C7 C8 1.361(6)
C7 C12 1.361(6)
C9 C10 1.378(5)
C9 C8 1.382(5)
C9 H9 0.9300
C1 C2 1.368(5)
C1 C6 1.380(5)
O1 N 1.212(4)
C11 C10 1.369(5)
C11 C12 1.377(5)
C11 H11 0.9300
N O2 1.210(4)
N C3 1.477(4)
C5 C6 1.380(5)
C5 C4 1.395(5)
C5 H5 0.9300
C4 C3 1.390(5)
C4 C10 1.484(5)
C2 C3 1.372(5)
C2 H2 0.9300
C6 H6 0.9300
C8 H8 0.9300
C12 H12 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 Br2 2_555 0.93 2.89 3.798(3) 165 yes
C9 H9 O2 8_655 0.93 2.57 3.454(5) 159 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1249273
