#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/32/8103233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8103233
loop_
_publ_author_name
'Xin-Li Zhang'
_publ_contact_author
;
Xin-Li Zhang
Department of Chemistry and Chemical Engineering, 
Baoji University of Arts and Sciences,
Baoji, Shaanxi  721013
People's Republic of China
;
_publ_section_title
;
 Crystal structure of
 2-bromo-4-chloro-6-[(4-chloro-phenylimino)methyl]phenol, C13H8BrCl2NO
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              567
_journal_volume                  226
_journal_year                    2011
_chemical_formula_sum            'C13 H8 Br Cl2 N O'
_chemical_formula_weight         345.01
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.138(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.712(2)
_cell_length_b                   21.437(5)
_cell_length_c                   8.541(2)
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.128
_cell_measurement_theta_min      2.762
_cell_volume                     1298.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11391
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_T_max  0.3168
_exptl_absorpt_correction_T_min  0.2917
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0365
_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)+(0.0345P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                2756
_reflns_number_total             3471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3565.cff
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        1298.3(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8103233
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.33546(4) 0.070489(12) 0.41978(3) 0.03157(9) Uani 1 1 d .
Cl1 Cl -0.12118(8) 0.19969(3) -0.15815(7) 0.02932(15) Uani 1 1 d .
Cl2 Cl 0.93131(10) 0.55644(3) 0.74447(8) 0.03467(16) Uani 1 1 d .
O1 O 0.5078(2) 0.19851(9) 0.5143(2) 0.0280(4) Uani 1 1 d .
N1 N 0.5257(3) 0.31904(9) 0.4862(2) 0.0247(4) Uani 1 1 d .
C1 C 0.3610(3) 0.20012(11) 0.3614(3) 0.0223(5) Uani 1 1 d .
C2 C 0.2637(3) 0.14535(11) 0.2925(3) 0.0235(5) Uani 1 1 d .
C3 C 0.1150(3) 0.14468(12) 0.1343(3) 0.0238(5) Uani 1 1 d .
H3 H 0.0506 0.1069 0.0884 0.029 Uiso 1 1 calc R
C4 C 0.0617(3) 0.20014(12) 0.0440(3) 0.0239(5) Uani 1 1 d .
C5 C 0.1517(3) 0.25520(12) 0.1104(3) 0.0236(5) Uani 1 1 d .
H5 H 0.1119 0.2928 0.0478 0.028 Uiso 1 1 calc R
C6 C 0.3014(3) 0.25598(11) 0.2695(3) 0.0211(5) Uani 1 1 d .
C7 C 0.3921(3) 0.31491(11) 0.3378(3) 0.0240(5) Uani 1 1 d .
H7 H 0.3515 0.3515 0.2707 0.029 Uiso 1 1 calc R
C8 C 0.6153(3) 0.37736(11) 0.5423(3) 0.0250(5) Uani 1 1 d .
C9 C 0.6956(3) 0.38856(12) 0.7173(3) 0.0281(5) Uani 1 1 d .
H9 H 0.6863 0.3579 0.7939 0.034 Uiso 1 1 calc R
C10 C 0.7891(4) 0.44425(12) 0.7805(3) 0.0295(6) Uani 1 1 d .
H10 H 0.8406 0.4523 0.8994 0.035 Uiso 1 1 calc R
C11 C 0.8060(3) 0.48756(11) 0.6681(3) 0.0258(5) Uani 1 1 d .
C12 C 0.7290(3) 0.47728(12) 0.4939(3) 0.0284(5) Uani 1 1 d .
H12 H 0.7412 0.5078 0.4181 0.034 Uiso 1 1 calc R
C13 C 0.6344(4) 0.42211(11) 0.4321(3) 0.0279(5) Uani 1 1 d .
H13 H 0.5817 0.4146 0.3129 0.033 Uiso 1 1 calc R
H1O H 0.547(5) 0.2353(14) 0.535(4) 0.050(10) Uiso 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
C1 O1 H1O 106(2)
C7 N1 C8 119.3(2)
O1 C1 C2 119.6(2)
O1 C1 C6 121.8(2)
C2 C1 C6 118.6(2)
C3 C2 C1 121.5(2)
C3 C2 Br1 119.57(18)
C1 C2 Br1 118.96(17)
C2 C3 C4 118.9(2)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 121.0(2)
C5 C4 Cl1 119.52(19)
C3 C4 Cl1 119.44(19)
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 119.8(2)
C5 C6 C7 119.1(2)
C1 C6 C7 121.1(2)
N1 C7 C6 122.0(2)
N1 C7 H7 119.0
C6 C7 H7 119.0
C13 C8 C9 119.0(2)
C13 C8 N1 123.1(2)
C9 C8 N1 117.8(2)
C10 C9 C8 120.5(2)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 119.0(2)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C12 121.5(2)
C10 C11 Cl2 120.00(18)
C12 C11 Cl2 118.46(19)
C13 C12 C11 119.1(2)
C13 C12 H12 120.5
C11 C12 H12 120.5
C12 C13 C8 120.8(2)
C12 C13 H13 119.6
C8 C13 H13 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.895(2)
Cl1 C4 1.748(2)
Cl2 C11 1.745(2)
O1 C1 1.351(3)
O1 H1O 0.84(3)
N1 C7 1.284(3)
N1 C8 1.418(3)
C1 C2 1.393(3)
C1 C6 1.406(3)
C2 C3 1.387(3)
C3 C4 1.388(3)
C3 H3 0.9500
C4 C5 1.374(3)
C5 C6 1.395(3)
C5 H5 0.9500
C6 C7 1.451(3)
C7 H7 0.9500
C8 C13 1.392(3)
C8 C9 1.396(3)
C9 C10 1.389(3)
C9 H9 0.9500
C10 C11 1.378(3)
C10 H10 0.9500
C11 C12 1.386(3)
C12 C13 1.381(3)
C12 H12 0.9500
C13 H13 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
O1 C1 C2 C3 -178.5(2)
C6 C1 C2 C3 2.2(3)
O1 C1 C2 Br1 2.1(3)
C6 C1 C2 Br1 -177.20(16)
C1 C2 C3 C4 -0.6(3)
Br1 C2 C3 C4 178.77(17)
C2 C3 C4 C5 -1.1(3)
C2 C3 C4 Cl1 178.23(17)
C3 C4 C5 C6 1.1(3)
Cl1 C4 C5 C6 -178.17(17)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -179.1(2)
O1 C1 C6 C5 178.6(2)
C2 C1 C6 C5 -2.1(3)
O1 C1 C6 C7 -1.9(3)
C2 C1 C6 C7 177.4(2)
C8 N1 C7 C6 176.8(2)
C5 C6 C7 N1 177.3(2)
C1 C6 C7 N1 -2.3(3)
C7 N1 C8 C13 -30.3(3)
C7 N1 C8 C9 152.9(2)
C13 C8 C9 C10 1.6(4)
N1 C8 C9 C10 178.6(2)
C8 C9 C10 C11 -1.8(4)
C9 C10 C11 C12 1.2(4)
C9 C10 C11 Cl2 -177.27(19)
C10 C11 C12 C13 -0.4(4)
Cl2 C11 C12 C13 178.05(19)
C11 C12 C13 C8 0.3(4)
C9 C8 C13 C12 -0.8(4)
N1 C8 C13 C12 -177.6(2)
