#------------------------------------------------------------------------------
#$Date: 2023-03-06 10:34:15 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281655 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106835.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_8106835
loop_
_publ_author_name
'Hong, Yong'
'Huang, Dushu'
'Liu, Wei'
'Zhang, Yinghong'
_publ_section_title
;
 Crystal structure of
 (E)-2,4-dibromo-6-(((2-nitrophenyl)imino)methyl)phenol, C13H8Br2N2O3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              231
_journal_page_last               232
_journal_paper_doi               10.1515/ncrs-2015-0100
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C13 H8 Br2 N2 O3'
_chemical_formula_sum            'C13 H8 Br2 N2 O3'
_chemical_formula_weight         400.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        '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                 93.355(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.794(3)
_cell_length_b                   7.2041(15)
_cell_length_c                   14.862(3)
_cell_measurement_reflns_used    1454
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      32.4
_cell_volume                     1367.5(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
scan:
	Number of images: 180
	           Slice: -122.0000 - 58.0000
	     Image width: 1.0000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 36.0000
	             XTD: 39.9101
	          2theta: -31.8549
scan:
	Number of images: 180
	           Slice: -122.0000 - 58.0000
	     Image width: 1.0000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -108.0000
	             XTD: 39.9101
	          2theta: -31.8549
scan:
	Number of images: 180
	           Slice: -200.0000 - -20.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 108.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 61
	           Slice: -200.0000 - -139.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 36.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 60
	           Slice: -80.0000 - -20.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 108.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 88
	           Slice: -125.0000 - -37.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 36.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 60
	           Slice: -124.0000 - -64.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 60
	           Slice: -119.0000 - -59.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -36.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 60
	           Slice: -87.0000 - -27.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -108.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 180
	           Slice: -200.0000 - -20.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -36.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 61
	           Slice: -200.0000 - -139.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 108.0000
	             XTD: 39.9101
	          2theta: -109.8549
scan:
	Number of images: 8
	           Slice: -185.0000 - -177.0000
	     Image width: 1.0000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 39.9101
	          2theta: -109.8549
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Pilatus 300K
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.042897
_diffrn_orient_matrix_UB_12      -0.024802
_diffrn_orient_matrix_UB_13      0.060625
_diffrn_orient_matrix_UB_21      -0.116087
_diffrn_orient_matrix_UB_22      0.032019
_diffrn_orient_matrix_UB_23      -0.069042
_diffrn_orient_matrix_UB_31      -0.003577
_diffrn_orient_matrix_UB_32      -0.063153
_diffrn_orient_matrix_UB_33      -0.023274
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8003
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         6.72
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    7.615
_exptl_absorpt_correction_T_max  0.5164
_exptl_absorpt_correction_T_min  0.2519
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0398
_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)+(0.0581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                1793
_reflns_number_total             1981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0100_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8106835
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C7(H7), C9(H9), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.05714(3) 0.59669(5) 0.29260(2) 0.0314(2) Uani 1 d . . .
Br2 Br 0.14282(4) 0.30701(6) -0.04929(3) 0.0461(2) Uani 1 d . . .
N1 N 0.5422(2) 0.2902(3) 0.45919(18) 0.0222(6) Uani 1 d . . .
N2 N 0.4774(2) 0.4385(3) 0.28812(17) 0.0198(6) Uani 1 d . . .
O1 O 0.5551(2) 0.3245(4) 0.53993(16) 0.0365(6) Uani 1 d . . .
O2 O 0.4707(2) 0.1948(3) 0.42710(16) 0.0326(6) Uani 1 d . . .
O3 O 0.2876(2) 0.5383(3) 0.32725(15) 0.0254(5) Uani 1 d . . .
H3 H 0.348(4) 0.523(5) 0.337(3) 0.021(10) Uiso 1 d . . .
C1 C 0.6185(3) 0.3643(4) 0.3990(2) 0.0202(7) Uani 1 d . . .
C2 C 0.7223(3) 0.3667(4) 0.4305(2) 0.0219(7) Uani 1 d . . .
H2 H 0.7419 0.3324 0.4909 0.026 Uiso 1 calc . . R
C3 C 0.7968(3) 0.4200(4) 0.3725(2) 0.0274(8) Uani 1 d . . .
H3A H 0.8687 0.4205 0.3925 0.033 Uiso 1 calc . . R
C4 C 0.7673(3) 0.4729(4) 0.2849(2) 0.0257(7) Uani 1 d . . .
H4 H 0.8193 0.5068 0.2449 0.031 Uiso 1 calc . . R
C5 C 0.6624(3) 0.4766(4) 0.2554(2) 0.0219(7) Uani 1 d . . .
H5 H 0.6431 0.5176 0.1959 0.026 Uiso 1 calc . . R
C6 C 0.5847(3) 0.4208(4) 0.3120(2) 0.0180(7) Uani 1 d . . .
C7 C 0.4412(2) 0.3997(4) 0.20820(19) 0.0181(7) Uani 1 d . . .
H7 H 0.4875 0.3547 0.1655 0.022 Uiso 1 calc . . R
C8 C 0.3306(3) 0.4229(4) 0.1812(2) 0.0192(7) Uani 1 d . . .
C9 C 0.2955(3) 0.3732(4) 0.0939(2) 0.0217(7) Uani 1 d . . .
H9 H 0.3439 0.3308 0.0524 0.026 Uiso 1 calc . . R
C10 C 0.1911(3) 0.3857(4) 0.0679(2) 0.0261(8) Uani 1 d . . .
C11 C 0.1186(3) 0.4495(4) 0.1268(2) 0.0260(7) Uani 1 d . . .
H11 H 0.0464 0.4576 0.1083 0.031 Uiso 1 calc . . R
C12 C 0.1539(3) 0.5010(4) 0.2130(2) 0.0219(7) Uani 1 d . . .
C13 C 0.2587(3) 0.4882(4) 0.2426(2) 0.0189(7) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 C1 117.9(3) . .
O2 N1 O1 123.5(3) . .
O2 N1 C1 118.6(3) . .
C7 N2 C6 120.7(3) . .
C13 O3 H3 110(3) . .
C2 C1 N1 117.4(3) . .
C2 C1 C6 123.2(3) . .
C6 C1 N1 119.4(3) . .
C1 C2 H2 120.7 . .
C3 C2 C1 118.5(3) . .
C3 C2 H2 120.7 . .
C2 C3 H3A 119.9 . .
C2 C3 C4 120.3(3) . .
C4 C3 H3A 119.9 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.5(3) . .
C5 C4 H4 119.7 . .
C4 C5 H5 119.6 . .
C4 C5 C6 120.8(3) . .
C6 C5 H5 119.6 . .
C1 C6 N2 120.3(3) . .
C5 C6 N2 122.7(3) . .
C5 C6 C1 116.6(3) . .
N2 C7 H7 119.2 . .
N2 C7 C8 121.5(3) . .
C8 C7 H7 119.2 . .
C9 C8 C7 118.7(3) . .
C9 C8 C13 120.0(3) . .
C13 C8 C7 121.3(3) . .
C8 C9 H9 120.0 . .
C10 C9 C8 120.0(3) . .
C10 C9 H9 120.0 . .
C9 C10 Br2 119.8(3) . .
C9 C10 C11 121.2(3) . .
C11 C10 Br2 118.9(3) . .
C10 C11 H11 120.7 . .
C12 C11 C10 118.5(3) . .
C12 C11 H11 120.7 . .
C11 C12 Br1 119.1(3) . .
C11 C12 C13 122.2(3) . .
C13 C12 Br1 118.7(2) . .
O3 C13 C8 122.7(3) . .
O3 C13 C12 119.2(3) . .
C12 C13 C8 118.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.892(3) .
Br2 C10 1.900(3) .
N1 O1 1.227(4) .
N1 O2 1.219(4) .
N1 C1 1.462(4) .
N2 C6 1.403(4) .
N2 C7 1.280(4) .
O3 H3 0.78(5) .
O3 C13 1.340(4) .
C1 C2 1.383(5) .
C1 C6 1.400(5) .
C2 H2 0.9500 .
C2 C3 1.377(5) .
C3 H3A 0.9500 .
C3 C4 1.387(5) .
C4 H4 0.9500 .
C4 C5 1.387(5) .
C5 H5 0.9500 .
C5 C6 1.398(5) .
C7 H7 0.9500 .
C7 C8 1.458(5) .
C8 C9 1.395(5) .
C8 C13 1.413(5) .
C9 H9 0.9500 .
C9 C10 1.372(5) .
C10 C11 1.391(5) .
C11 H11 0.9500 .
C11 C12 1.384(5) .
C12 C13 1.389(5) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Br1 C12 C13 O3 2.1(4) . . . .
Br1 C12 C13 C8 -177.7(2) . . . .
Br2 C10 C11 C12 178.0(2) . . . .
N1 C1 C2 C3 174.2(3) . . . .
N1 C1 C6 N2 11.6(4) . . . .
N1 C1 C6 C5 -175.2(2) . . . .
N2 C7 C8 C9 -178.2(3) . . . .
N2 C7 C8 C13 -0.4(4) . . . .
O1 N1 C1 C2 37.7(4) . . . .
O1 N1 C1 C6 -145.2(3) . . . .
O2 N1 C1 C2 -140.8(3) . . . .
O2 N1 C1 C6 36.4(4) . . . .
C1 C2 C3 C4 1.1(5) . . . .
C2 C1 C6 N2 -171.4(3) . . . .
C2 C1 C6 C5 1.8(4) . . . .
C2 C3 C4 C5 1.4(5) . . . .
C3 C4 C5 C6 -2.4(5) . . . .
C4 C5 C6 N2 173.9(3) . . . .
C4 C5 C6 C1 0.8(4) . . . .
C6 N2 C7 C8 -178.0(3) . . . .
C6 C1 C2 C3 -2.8(5) . . . .
C7 N2 C6 C1 -145.4(3) . . . .
C7 N2 C6 C5 41.7(4) . . . .
C7 C8 C9 C10 177.1(3) . . . .
C7 C8 C13 O3 2.3(4) . . . .
C7 C8 C13 C12 -177.9(3) . . . .
C8 C9 C10 Br2 -177.1(2) . . . .
C8 C9 C10 C11 0.8(5) . . . .
C9 C8 C13 O3 -179.9(3) . . . .
C9 C8 C13 C12 -0.1(4) . . . .
C9 C10 C11 C12 0.1(5) . . . .
C10 C11 C12 Br1 177.7(2) . . . .
C10 C11 C12 C13 -1.0(5) . . . .
C11 C12 C13 O3 -179.2(3) . . . .
C11 C12 C13 C8 1.0(4) . . . .
C13 C8 C9 C10 -0.8(4) . . . .
