#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/67/2216771.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_2216771
loop_
_publ_author_name
'Guo, Ming-Lin'
'Zhang, Li'
_publ_section_title
;
 2,4-Dibromo-6-(4-bromophenyliminomethyl)phenol
;
_journal_coeditor_code           SJ2397
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4558
_journal_page_last               o4558
_journal_paper_doi               10.1107/S1600536807054335
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H8 Br3 N O'
_chemical_formula_moiety         'C13 H8 Br3 N O'
_chemical_formula_sum            'C13 H8 Br3 N O'
_chemical_formula_weight         433.90
_chemical_name_systematic
;
2,4-Dibromo-6-(4-bromophenyliminomethyl)phenol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.801(6)
_cell_angle_beta                 76.688(7)
_cell_angle_gamma                65.180(5)
_cell_formula_units_Z            2
_cell_length_a                   7.985(3)
_cell_length_b                   8.594(3)
_cell_length_c                   11.020(4)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.89
_cell_volume                     666.5(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.1147
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3322
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.065
_exptl_absorpt_correction_T_max  0.339
_exptl_absorpt_correction_T_min  0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.863
_refine_diff_density_min         -1.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                1471
_reflns_number_total             2309
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2397.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2216771
_cod_database_fobs_code          2216771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
Br Br1 0.12496(17) 0.33749(14) 0.12113(9) 0.0560(4) Uani d . 1
Br Br2 0.69858(18) 0.14000(16) 0.98515(10) 0.0616(5) Uani d . 1
Br Br3 -0.19458(18) 1.03572(14) 0.29251(11) 0.0597(5) Uani d . 1
O O1 0.2910(9) 0.2930(9) 0.3421(6) 0.0451(18) Uani d . 1
H H1 0.2990 0.2748 0.4146 0.054 Uiso d R 1
N N1 0.3470(10) 0.3870(10) 0.5425(7) 0.0350(19) Uani d . 1
C C1 0.1501(12) 0.5864(12) 0.4244(8) 0.032(2) Uani d . 1
C C2 0.1817(12) 0.4586(11) 0.3349(8) 0.030(2) Uani d . 1
C C3 0.0952(13) 0.5088(13) 0.2346(8) 0.035(2) Uani d . 1
C C4 -0.0163(12) 0.6781(11) 0.2222(8) 0.030(2) Uani d . 1
H H4 -0.0730 0.7103 0.1549 0.036 Uiso calc R 1
C C5 -0.0428(12) 0.8008(12) 0.3121(9) 0.034(2) Uani d . 1
C C6 0.0394(13) 0.7551(12) 0.4103(8) 0.035(2) Uani d . 1
H H6 0.0203 0.8394 0.4690 0.042 Uiso calc R 1
C C7 0.2360(13) 0.5403(13) 0.5293(9) 0.037(2) Uani d . 1
H H7 0.2093 0.6258 0.5894 0.044 Uiso calc R 1
C C8 0.4295(12) 0.3389(12) 0.6481(8) 0.032(2) Uani d . 1
C C9 0.5304(14) 0.1652(12) 0.6570(9) 0.041(2) Uani d . 1
H H9 0.5436 0.0877 0.5950 0.049 Uiso calc R 1
C C10 0.6116(15) 0.1055(14) 0.7560(10) 0.049(3) Uani d . 1
H H10 0.6817 -0.0116 0.7603 0.059 Uiso calc R 1
C C11 0.5887(13) 0.2199(13) 0.8488(9) 0.042(3) Uani d . 1
C C12 0.4891(15) 0.3947(14) 0.8395(9) 0.048(3) Uani d . 1
H H12 0.4767 0.4728 0.9009 0.057 Uiso calc R 1
C C13 0.4093(13) 0.4518(12) 0.7400(8) 0.037(2) Uani d . 1
H H13 0.3405 0.5690 0.7348 0.044 Uiso calc R 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 0.0849(8) 0.0393(7) 0.0331(6) -0.0047(5) -0.0351(6) -0.0061(5)
Br2 0.0917(9) 0.0532(8) 0.0349(7) -0.0119(6) -0.0432(6) 0.0077(5)
Br3 0.0896(9) 0.0281(7) 0.0566(8) -0.0077(6) -0.0431(6) 0.0098(5)
O1 0.061(4) 0.039(4) 0.023(4) -0.001(3) -0.026(3) 0.003(3)
N1 0.044(4) 0.033(5) 0.028(4) -0.011(4) -0.022(3) 0.006(4)
C1 0.044(5) 0.034(5) 0.018(5) -0.014(4) -0.015(4) 0.007(4)
C2 0.039(5) 0.024(5) 0.017(4) -0.001(4) -0.011(4) 0.000(4)
C3 0.047(5) 0.047(7) 0.017(5) -0.020(5) -0.016(4) 0.005(4)
C4 0.045(5) 0.030(5) 0.014(4) -0.010(4) -0.017(4) 0.006(4)
C5 0.044(5) 0.026(5) 0.039(6) -0.015(4) -0.020(4) 0.016(4)
C6 0.060(6) 0.027(6) 0.025(5) -0.018(5) -0.022(4) 0.005(4)
C7 0.053(6) 0.035(6) 0.032(5) -0.020(5) -0.024(4) 0.003(4)
C8 0.037(5) 0.045(6) 0.014(4) -0.014(4) -0.014(4) 0.007(4)
C9 0.062(6) 0.029(6) 0.036(6) -0.015(5) -0.030(5) 0.001(4)
C10 0.067(7) 0.031(6) 0.046(6) -0.006(5) -0.037(5) 0.002(5)
C11 0.050(6) 0.043(6) 0.026(5) -0.007(5) -0.021(4) 0.005(4)
C12 0.077(7) 0.041(7) 0.032(6) -0.022(6) -0.034(5) 0.013(5)
C13 0.053(5) 0.021(5) 0.028(5) -0.004(4) -0.017(4) -0.003(4)
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 O1 H1 109.4
C7 N1 C8 122.6(8)
C6 C1 C2 119.8(8)
C6 C1 C7 120.1(9)
C2 C1 C7 120.1(8)
O1 C2 C3 119.2(8)
O1 C2 C1 122.6(8)
C3 C2 C1 118.2(8)
C4 C3 C2 121.3(8)
C4 C3 Br1 120.5(6)
C2 C3 Br1 118.2(7)
C3 C4 C5 118.7(8)
C3 C4 H4 120.6
C5 C4 H4 120.6
C6 C5 C4 121.0(8)
C6 C5 Br3 120.6(8)
C4 C5 Br3 118.4(6)
C5 C6 C1 120.9(9)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C1 122.2(9)
N1 C7 H7 118.9
C1 C7 H7 118.9
C13 C8 C9 119.3(8)
C13 C8 N1 124.5(8)
C9 C8 N1 116.2(8)
C10 C9 C8 120.8(9)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 119.6(10)
C9 C10 H10 120.2
C11 C10 H10 120.2
C10 C11 C12 119.8(9)
C10 C11 Br2 120.0(8)
C12 C11 Br2 120.1(8)
C13 C12 C11 119.8(10)
C13 C12 H12 120.1
C11 C12 H12 120.1
C8 C13 C12 120.8(9)
C8 C13 H13 119.6
C12 C13 H13 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.870(10)
Br2 C11 1.876(9)
Br3 C5 1.904(9)
O1 C2 1.332(11)
O1 H1 0.8200
N1 C7 1.268(12)
N1 C8 1.431(10)
C1 C6 1.370(13)
C1 C2 1.406(13)
C1 C7 1.437(12)
C2 C3 1.397(12)
C3 C4 1.372(13)
C4 C5 1.390(13)
C4 H4 0.9300
C5 C6 1.354(12)
C6 H6 0.9300
C7 H7 0.9300
C8 C13 1.365(13)
C8 C9 1.379(13)
C9 C10 1.371(13)
C9 H9 0.9300
C10 C11 1.373(14)
C10 H10 0.9300
C11 C12 1.387(15)
C12 C13 1.367(13)
C12 H12 0.9300
C13 H13 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
O1 H1 N1 . 0.82 1.93 2.574(10) 134.6
C10 H10 O1 2_656 0.93 2.61 3.341(13) 135.7
C10 H10 Br1 2_656 0.93 2.99 3.866(10) 157.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655392
