#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239766.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_2239766
loop_
_publ_author_name
'Yan, Xu-Xiu'
'Lu, Li-Ping'
'Zhu, Miao-Li'
_publ_section_title
;
 4-Bromo-2-[(phenylimino)methyl]phenol
;
_journal_coeditor_code           NK2224
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o853
_journal_paper_doi               10.1107/S1600536814015268
_journal_volume                  70
_journal_year                    2014
_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-2-[(phenylimino)methyl]phenol
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   12.353(3)
_cell_length_b                   4.5092(9)
_cell_length_c                   19.778(4)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.07
_cell_volume                     1101.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4926
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    3.706
_exptl_absorpt_correction_T_max  0.8364
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.333
_refine_ls_abs_structure_details 'Flack (1983), 924 Friedel pairs'
_refine_ls_abs_structure_Flack   0.039(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0386
_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)+(0.0329P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                1444
_reflns_number_total             1674
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2224sup1.cif
_cod_data_source_block           I
_cod_database_code               2239766
_cod_database_fobs_code          2239766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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 0.57515(4) 1.03271(10) 0.49809(4) 0.04069(18) Uani d . 1 1
C C1 0.6938(4) 0.5393(12) 0.3358(3) 0.0283(13) Uani d . 1 1
C C2 0.8024(4) 0.6143(12) 0.3347(3) 0.0310(14) Uani d . 1 1
C C3 0.8434(5) 0.8206(15) 0.3824(3) 0.0401(16) Uani d . 1 1
H H3 0.9163 0.8720 0.3817 0.048 Uiso calc R 1 1
C C4 0.7755(5) 0.9449(13) 0.4299(3) 0.0394(14) Uani d . 1 1
H H4 0.8022 1.0819 0.4608 0.047 Uiso calc R 1 1
C C5 0.6671(5) 0.8650(13) 0.4313(3) 0.0340(14) Uani d . 1 1
C C6 0.6257(5) 0.6708(12) 0.3845(3) 0.0315(13) Uani d . 1 1
H H6 0.5523 0.6255 0.3850 0.038 Uiso calc R 1 1
C C7 0.6489(4) 0.3280(12) 0.2878(3) 0.0305(13) Uani d . 1 1
H H7 0.5750 0.2881 0.2882 0.037 Uiso calc R 1 1
C C8 0.6684(4) -0.0149(12) 0.1984(3) 0.0314(13) Uani d . 1 1
C C9 0.5609(5) -0.1095(13) 0.1966(3) 0.0379(15) Uani d . 1 1
H H9 0.5108 -0.0327 0.2271 0.045 Uiso calc R 1 1
C C10 0.5286(5) -0.3203(13) 0.1487(3) 0.0428(17) Uani d . 1 1
H H10 0.4573 -0.3866 0.1481 0.051 Uiso calc R 1 1
C C11 0.6026(5) -0.4316(12) 0.1020(3) 0.0401(15) Uani d . 1 1
H H11 0.5810 -0.5689 0.0695 0.048 Uiso calc R 1 1
C C12 0.7067(6) -0.3361(15) 0.1046(4) 0.0445(16) Uani d . 1 1
H H12 0.7565 -0.4105 0.0736 0.053 Uiso calc R 1 1
C C13 0.7409(5) -0.1310(12) 0.1521(3) 0.0373(14) Uani d . 1 1
H H13 0.8130 -0.0710 0.1528 0.045 Uiso calc R 1 1
N N1 0.7101(4) 0.1963(10) 0.2449(2) 0.0304(12) Uani d . 1 1
O O1 0.8726(3) 0.4998(10) 0.2894(2) 0.0398(10) Uani d . 1 1
H H1 0.840(4) 0.348(13) 0.269(3) 0.029(17) Uiso 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'
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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.1(5)
C2 C1 C7 121.4(5)
C6 C1 C7 119.6(5)
O1 C2 C1 122.6(5)
O1 C2 C3 117.6(5)
C1 C2 C3 119.8(6)
C4 C3 C2 120.1(6)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 119.8(6)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 120.7(6)
C6 C5 Br1 120.0(4)
C4 C5 Br1 119.2(5)
C5 C6 C1 120.5(5)
C5 C6 H6 119.8
C1 C6 H6 119.8
N1 C7 C1 120.6(5)
N1 C7 H7 119.7
C1 C7 H7 119.7
C13 C8 C9 118.9(5)
C13 C8 N1 116.6(5)
C9 C8 N1 124.5(5)
C8 C9 C10 119.7(6)
C8 C9 H9 120.1
C10 C9 H9 120.1
C11 C10 C9 120.4(6)
C11 C10 H10 119.8
C9 C10 H10 119.8
C12 C11 C10 118.8(6)
C12 C11 H11 120.6
C10 C11 H11 120.6
C11 C12 C13 121.8(7)
C11 C12 H12 119.1
C13 C12 H12 119.1
C12 C13 C8 120.3(6)
C12 C13 H13 119.8
C8 C13 H13 119.8
C7 N1 C8 121.6(5)
C2 O1 H1 108(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.899(6)
C1 C2 1.383(7)
C1 C6 1.411(8)
C1 C7 1.454(8)
C2 O1 1.350(7)
C2 C3 1.419(9)
C3 C4 1.378(9)
C3 H3 0.9300
C4 C5 1.387(8)
C4 H4 0.9300
C5 C6 1.372(8)
C6 H6 0.9300
C7 N1 1.283(7)
C7 H7 0.9300
C8 C13 1.385(8)
C8 C9 1.396(7)
C8 N1 1.421(7)
C9 C10 1.400(8)
C9 H9 0.9300
C10 C11 1.394(9)
C10 H10 0.9300
C11 C12 1.358(9)
C11 H11 0.9300
C12 C13 1.384(8)
C12 H12 0.9300
C13 H13 0.9300
O1 H1 0.89(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 0.89(6) 1.81(5) 2.583(6) 144(5) y
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 O1 -179.6(5)
C7 C1 C2 O1 0.5(9)
C6 C1 C2 C3 0.1(8)
C7 C1 C2 C3 -179.8(5)
O1 C2 C3 C4 180.0(5)
C1 C2 C3 C4 0.3(9)
C2 C3 C4 C5 0.8(9)
C3 C4 C5 C6 -2.2(9)
C3 C4 C5 Br1 178.8(5)
C4 C5 C6 C1 2.6(9)
Br1 C5 C6 C1 -178.4(4)
C2 C1 C6 C5 -1.6(8)
C7 C1 C6 C5 178.4(5)
C2 C1 C7 N1 2.9(8)
C6 C1 C7 N1 -177.0(5)
C13 C8 C9 C10 0.6(9)
N1 C8 C9 C10 -179.7(5)
C8 C9 C10 C11 -1.4(9)
C9 C10 C11 C12 1.2(9)
C10 C11 C12 C13 -0.3(10)
C11 C12 C13 C8 -0.5(10)
C9 C8 C13 C12 0.4(9)
N1 C8 C13 C12 -179.4(5)
C1 C7 N1 C8 178.8(5)
C13 C8 N1 C7 176.6(5)
C9 C8 N1 C7 -3.1(9)
