#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/39/2233996.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_2233996
loop_
_publ_author_name
'Jothi, L.'
'Vasuki, G.'
'Babu, R. Ramesh'
'Ramamurthi, K.'
_publ_section_title
;
 4-Bromo-N-(4-hydroxybenzylidene)aniline
;
_journal_coeditor_code           SJ5193
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o772
_journal_paper_doi               10.1107/S1600536812006101
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H10 Br N O'
_chemical_formula_moiety         'C13 H10 Br N O'
_chemical_formula_sum            'C13 H10 Br N O'
_chemical_formula_weight         276.13
_chemical_name_systematic
;
4-Bromo-N-(4-hydroxybenzylidene)aniline
;
_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                   21.9588(10)
_cell_length_b                   11.0866(5)
_cell_length_c                   9.3132(4)
_cell_measurement_reflns_used    6133
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.7
_cell_volume                     2267.28(17)
_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) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.602
_exptl_absorpt_correction_T_max  0.571
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.324
_refine_diff_density_min         -1.617
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0898P)²+6.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                1494
_reflns_number_total             2001
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5193.cif
_cod_data_source_block           I
_cod_database_code               2233996
_cod_database_fobs_code          2233996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
C C1 0.3296(2) 0.1888(4) -0.1451(5) 0.0340(10) Uani d . 1 1
C C2 0.3501(2) 0.0799(4) -0.0885(5) 0.0398(11) Uani d . 1 1
H H2 0.3879 0.0493 -0.1156 0.048 Uiso calc R 1 1
C C3 0.3145(2) 0.0181(4) 0.0074(5) 0.0407(11) Uani d . 1 1
H H3 0.3283 -0.0551 0.0437 0.049 Uiso calc R 1 1
C C4 0.2586(2) 0.0620(4) 0.0514(5) 0.0333(10) Uani d . 1 1
C C5 0.2389(2) 0.1715(4) -0.0048(4) 0.0340(10) Uani d . 1 1
H H5 0.2014 0.2027 0.0231 0.041 Uiso calc R 1 1
C C6 0.2743(2) 0.2341(4) -0.1012(5) 0.0340(10) Uani d . 1 1
H H6 0.2607 0.3076 -0.1370 0.041 Uiso calc R 1 1
C C7 0.2200(2) -0.0109(4) 0.1437(5) 0.0360(10) Uani d . 1 1
H H7 0.2321 -0.0899 0.1619 0.043 Uiso calc R 1 1
C C8 0.1337(2) -0.0598(4) 0.2718(5) 0.0342(10) Uani d . 1 1
C C9 0.1277(2) -0.1783(5) 0.2249(6) 0.0456(12) Uani d . 1 1
H H9 0.1487 -0.2041 0.1439 0.055 Uiso calc R 1 1
C C10 0.0909(3) -0.2569(5) 0.2975(6) 0.0518(13) Uani d . 1 1
H H10 0.0870 -0.3359 0.2654 0.062 Uiso calc R 1 1
C C11 0.0598(2) -0.2199(5) 0.4172(6) 0.0526(14) Uani d . 1 1
C C12 0.0639(2) -0.1040(5) 0.4635(6) 0.0518(13) Uani d . 1 1
H H12 0.0426 -0.0793 0.5445 0.062 Uiso calc R 1 1
C C13 0.1002(2) -0.0229(5) 0.3893(5) 0.0450(12) Uani d . 1 1
H H13 0.1020 0.0571 0.4189 0.054 Uiso calc R 1 1
N N1 0.17101(17) 0.0253(3) 0.2012(4) 0.0342(9) Uani d . 1 1
O O1 0.36520(16) 0.2436(3) -0.2426(4) 0.0465(9) Uani d . 1 1
H H1 0.3522 0.3116 -0.2583 0.070 Uiso calc R 1 1
Br Br1 0.01108(4) -0.33090(9) 0.51718(9) 0.0918(4) Uani d . 1 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'
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
O1 C1 C6 123.4(4)
O1 C1 C2 117.4(4)
C6 C1 C2 119.3(4)
C3 C2 C1 119.7(4)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 121.6(4)
C2 C3 H3 119.2
C4 C3 H3 119.2
C3 C4 C5 118.2(4)
C3 C4 C7 119.8(4)
C5 C4 C7 121.8(4)
C6 C5 C4 120.6(4)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 120.6(4)
C5 C6 H6 119.7
C1 C6 H6 119.7
N1 C7 C4 124.7(4)
N1 C7 H7 117.7
C4 C7 H7 117.7
C13 C8 C9 118.6(4)
C13 C8 N1 118.7(4)
C9 C8 N1 122.6(4)
C10 C9 C8 120.2(5)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 120.4(5)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 120.5(5)
C12 C11 Br1 120.0(4)
C10 C11 Br1 119.4(4)
C11 C12 C13 119.6(5)
C11 C12 H12 120.2
C13 C12 H12 120.2
C8 C13 C12 120.6(5)
C8 C13 H13 119.7
C12 C13 H13 119.7
C7 N1 C8 118.6(4)
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.343(5)
C1 C6 1.376(6)
C1 C2 1.392(6)
C2 C3 1.371(7)
C2 H2 0.9300
C3 C4 1.382(7)
C3 H3 0.9300
C4 C5 1.391(6)
C4 C7 1.454(6)
C5 C6 1.375(6)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.267(6)
C7 H7 0.9300
C8 C13 1.380(7)
C8 C9 1.390(7)
C8 N1 1.412(6)
C9 C10 1.367(7)
C9 H9 0.9300
C10 C11 1.370(9)
C10 H10 0.9300
C11 C12 1.358(8)
C11 Br1 1.878(5)
C12 C13 1.386(7)
C12 H12 0.9300
C13 H13 0.9300
O1 H1 0.8200
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
O1 H1 N1 2_554 0.82 1.916 2.734 174.92
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
O1 C1 C2 C3 -177.6(4)
C6 C1 C2 C3 1.5(7)
C1 C2 C3 C4 -0.9(7)
C2 C3 C4 C5 0.2(7)
C2 C3 C4 C7 174.8(4)
C3 C4 C5 C6 -0.1(6)
C7 C4 C5 C6 -174.6(4)
C4 C5 C6 C1 0.7(6)
O1 C1 C6 C5 177.6(4)
C2 C1 C6 C5 -1.4(7)
C3 C4 C7 N1 172.7(4)
C5 C4 C7 N1 -12.9(7)
C13 C8 C9 C10 -2.2(7)
N1 C8 C9 C10 179.9(5)
C8 C9 C10 C11 -0.2(8)
C9 C10 C11 C12 1.5(8)
C9 C10 C11 Br1 -178.6(4)
C10 C11 C12 C13 -0.4(8)
Br1 C11 C12 C13 179.7(4)
C9 C8 C13 C12 3.4(7)
N1 C8 C13 C12 -178.7(4)
C11 C12 C13 C8 -2.2(8)
C4 C7 N1 C8 171.2(4)
C13 C8 N1 C7 147.7(4)
C9 C8 N1 C7 -34.5(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12624754
