#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/27/2232751.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_2232751
loop_
_publ_author_name
'Zhao, Pei-Hua'
'Feng, Zhan-Heng'
'Zhang, Mei'
'Liu, Ya-Qing'
'Zhao, Gui-Zhe'
_publ_section_title
;
 1-Bromo-2-[(E)-2-nitroethenyl]benzene
;
_journal_coeditor_code           HB6539
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3505
_journal_paper_doi               10.1107/S1600536811050963
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H6 Br N O2'
_chemical_formula_moiety         'C8 H6 Br N O2'
_chemical_formula_sum            'C8 H6 Br N O2'
_chemical_formula_weight         228.05
_chemical_name_systematic
;
1-Bromo-2-[(E)-2-nitroethenyl]benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.336(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9570(18)
_cell_length_b                   15.646(2)
_cell_length_c                   7.9470(13)
_cell_measurement_reflns_used    2970
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.6
_cell_volume                     816.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10346
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.989
_exptl_absorpt_correction_T_max  0.5024
_exptl_absorpt_correction_T_min  0.4353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.782
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                1466
_reflns_number_total             1945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6539.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232751
_cod_database_fobs_code          2232751
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.39712(4) 0.607142(14) 0.81215(3) 0.02051(8) Uani d . 1 1
O O1 0.1113(2) 0.21839(10) 0.6270(2) 0.0218(4) Uani d . 1 1
O O2 0.3362(2) 0.29119(10) 0.8336(2) 0.0238(4) Uani d . 1 1
N N1 0.2150(3) 0.28344(11) 0.6807(2) 0.0153(4) Uani d . 1 1
C C1 0.3043(3) 0.58570(14) 0.5620(3) 0.0141(5) Uani d . 1 1
C C2 0.2914(3) 0.65593(14) 0.4508(3) 0.0153(5) Uani d . 1 1
H H2 0.3316 0.7109 0.5007 0.018 Uiso calc R 1 1
C C3 0.2203(3) 0.64552(14) 0.2684(3) 0.0179(5) Uani d . 1 1
H H3 0.2093 0.6935 0.1925 0.021 Uiso calc R 1 1
C C4 0.1644(3) 0.56451(15) 0.1954(3) 0.0190(5) Uani d . 1 1
H H4 0.1156 0.5571 0.0696 0.023 Uiso calc R 1 1
C C5 0.1804(3) 0.49484(14) 0.3071(3) 0.0160(5) Uani d . 1 1
H H5 0.1438 0.4398 0.2561 0.019 Uiso calc R 1 1
C C6 0.2490(3) 0.50341(13) 0.4930(3) 0.0119(4) Uani d . 1 1
C C7 0.2672(3) 0.42903(13) 0.6100(3) 0.0132(5) Uani d . 1 1
H H7 0.3405 0.4360 0.7334 0.016 Uiso calc R 1 1
C C8 0.1882(3) 0.35266(13) 0.5549(3) 0.0135(5) Uani d . 1 1
H H8 0.1138 0.3435 0.4324 0.016 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 0.02929(14) 0.01733(14) 0.01372(13) -0.00098(11) 0.00552(10) -0.00406(9)
O1 0.0270(10) 0.0133(8) 0.0233(9) -0.0033(7) 0.0058(8) 0.0004(7)
O2 0.0272(10) 0.0228(9) 0.0148(9) 0.0010(7) -0.0020(7) 0.0036(7)
N1 0.0178(10) 0.0113(10) 0.0182(10) 0.0032(8) 0.0079(8) 0.0012(8)
C1 0.0107(11) 0.0190(12) 0.0120(11) 0.0007(9) 0.0032(9) -0.0014(9)
C2 0.0151(12) 0.0119(12) 0.0207(13) -0.0022(9) 0.0081(10) -0.0021(9)
C3 0.0178(12) 0.0158(12) 0.0207(13) -0.0014(10) 0.0074(10) 0.0057(10)
C4 0.0211(13) 0.0227(14) 0.0122(12) -0.0046(10) 0.0042(10) -0.0008(10)
C5 0.0173(12) 0.0146(12) 0.0161(12) -0.0010(9) 0.0056(10) -0.0023(9)
C6 0.0099(11) 0.0113(11) 0.0148(12) 0.0014(8) 0.0046(9) 0.0015(9)
C7 0.0119(11) 0.0150(12) 0.0124(11) 0.0032(9) 0.0037(9) 0.0005(9)
C8 0.0164(12) 0.0132(12) 0.0111(12) 0.0047(9) 0.0050(9) 0.0037(9)
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
O2 N1 O1 123.39(19)
O2 N1 C8 119.86(18)
O1 N1 C8 116.75(18)
C2 C1 C6 121.6(2)
C2 C1 Br1 116.81(16)
C6 C1 Br1 121.57(16)
C3 C2 C1 119.9(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 119.9(2)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 119.7(2)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.8(2)
C4 C5 H5 119.1
C6 C5 H5 119.1
C1 C6 C5 116.97(19)
C1 C6 C7 121.70(19)
C5 C6 C7 121.31(19)
C8 C7 C6 124.4(2)
C8 C7 H7 117.8
C6 C7 H7 117.8
C7 C8 N1 120.14(19)
C7 C8 H8 119.9
N1 C8 H8 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.906(2)
O1 N1 1.239(2)
O2 N1 1.234(2)
N1 C8 1.444(3)
C1 C2 1.394(3)
C1 C6 1.402(3)
C2 C3 1.377(3)
C2 H2 0.9500
C3 C4 1.395(3)
C3 H3 0.9500
C4 C5 1.387(3)
C4 H4 0.9500
C5 C6 1.401(3)
C5 H5 0.9500
C6 C7 1.468(3)
C7 C8 1.328(3)
C7 H7 0.9500
C8 H8 0.9500
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
C6 C1 C2 C3 0.9(3)
Br1 C1 C2 C3 -178.25(16)
C1 C2 C3 C4 -1.0(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 0.9(4)
C2 C1 C6 C5 0.1(3)
Br1 C1 C6 C5 179.22(16)
C2 C1 C6 C7 178.5(2)
Br1 C1 C6 C7 -2.4(3)
C4 C5 C6 C1 -1.0(3)
C4 C5 C6 C7 -179.4(2)
C1 C6 C7 C8 168.8(2)
C5 C6 C7 C8 -13.0(3)
C6 C7 C8 N1 179.9(2)
O2 N1 C8 C7 -10.9(3)
O1 N1 C8 C7 168.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4530997
