#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233859.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_2233859
loop_
_publ_author_name
'Zhu, Jing'
'Li, Ming'
'Wei, Hong-xia'
'Wang, Jian-qiang'
'Guo, Cheng'
_publ_section_title
;
 2,6-Dichloro-N-(4-chlorophenyl)benzamide
;
_journal_coeditor_code           HB6644
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o843
_journal_paper_doi               10.1107/S1600536812007556
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H8 Cl3 N O'
_chemical_formula_moiety         'C13 H8 Cl3 N O'
_chemical_formula_sum            'C13 H8 Cl3 N O'
_chemical_formula_weight         300.55
_chemical_melting_point          397
_chemical_name_systematic
;
2,6-Dichloro-N-(4-chlorophenyl)benzamide
;
_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                 100.60(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.241(2)
_cell_length_b                   12.590(3)
_cell_length_c                   9.6450(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1341.7(5)
_computing_cell_refinement       'CAD4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2587
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_correction_T_min  0.8248
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0565
_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)+(0.0950P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1809
_reflns_number_gt                1481
_reflns_number_total             2459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6644.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233859
_cod_database_fobs_code          2233859
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_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
N N 0.7580(3) 0.3117(2) 0.1127(3) 0.0423(8) Uani d . 1 1
H H0A 0.7677 0.2870 0.1972 0.051 Uiso calc R 1 1
O O 0.7776(3) 0.2668(2) -0.1093(3) 0.0660(9) Uani d . 1 1
Cl Cl1 0.57123(16) 0.75067(10) 0.0703(2) 0.1055(6) Uani d . 1 1
C C1 0.7243(4) 0.4801(4) -0.0171(5) 0.0593(12) Uani d . 1 1
H H1A 0.7651 0.4547 -0.0859 0.071 Uiso calc R 1 1
Cl Cl2 0.64198(10) 0.05573(10) 0.07481(12) 0.0617(4) Uani d . 1 1
C C2 0.6810(5) 0.5830(4) -0.0246(5) 0.0668(13) Uani d . 1 1
H H2A 0.6917 0.6268 -0.0990 0.080 Uiso calc R 1 1
Cl Cl3 1.06285(13) 0.25773(11) 0.06642(19) 0.0927(6) Uani d . 1 1
C C3 0.6224(4) 0.6202(4) 0.0774(6) 0.0594(12) Uani d . 1 1
C C4 0.6040(4) 0.5568(4) 0.1854(6) 0.0660(13) Uani d . 1 1
H H4A 0.5638 0.5829 0.2543 0.079 Uiso calc R 1 1
C C5 0.6460(4) 0.4524(4) 0.1924(5) 0.0544(11) Uani d . 1 1
H H5A 0.6323 0.4082 0.2652 0.065 Uiso calc R 1 1
C C6 0.7070(3) 0.4148(3) 0.0926(4) 0.0394(9) Uani d . 1 1
C C7 0.7928(4) 0.2481(3) 0.0165(4) 0.0443(10) Uani d . 1 1
C C8 0.8579(4) 0.1497(3) 0.0788(4) 0.0434(10) Uani d . 1 1
C C9 0.7988(4) 0.0590(3) 0.1085(4) 0.0465(10) Uani d . 1 1
C C10 0.8603(5) -0.0302(4) 0.1654(5) 0.0595(12) Uani d . 1 1
H H10A 0.8188 -0.0911 0.1831 0.071 Uiso calc R 1 1
C C11 0.9838(5) -0.0267(5) 0.1951(6) 0.0765(15) Uani d . 1 1
H H11A 1.0264 -0.0859 0.2346 0.092 Uiso calc R 1 1
C C12 1.0461(5) 0.0615(5) 0.1683(6) 0.0753(15) Uani d . 1 1
H H12A 1.1302 0.0628 0.1906 0.090 Uiso calc R 1 1
C C13 0.9836(4) 0.1479(4) 0.1082(5) 0.0593(12) Uani d . 1 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
N 0.055(2) 0.0430(19) 0.0289(16) 0.0040(16) 0.0070(14) 0.0032(15)
O 0.109(3) 0.0540(19) 0.0365(17) 0.0039(17) 0.0164(17) -0.0042(14)
Cl1 0.1079(13) 0.0498(8) 0.1576(16) 0.0283(8) 0.0215(11) 0.0106(9)
C1 0.077(3) 0.052(3) 0.051(3) 0.006(2) 0.018(2) 0.010(2)
Cl2 0.0515(7) 0.0637(7) 0.0707(8) -0.0022(5) 0.0132(5) 0.0087(6)
C2 0.085(4) 0.046(3) 0.068(3) 0.004(3) 0.011(3) 0.016(2)
Cl3 0.0706(9) 0.0743(10) 0.1392(14) -0.0252(7) 0.0347(9) -0.0239(9)
C3 0.048(3) 0.043(3) 0.084(4) 0.003(2) 0.002(2) 0.003(2)
C4 0.063(3) 0.063(3) 0.078(3) 0.013(2) 0.028(3) -0.007(3)
C5 0.062(3) 0.052(3) 0.053(3) 0.004(2) 0.019(2) 0.006(2)
C6 0.042(2) 0.036(2) 0.039(2) -0.0007(17) 0.0032(17) -0.0009(17)
C7 0.058(3) 0.044(2) 0.031(2) -0.0057(19) 0.0088(18) -0.0004(18)
C8 0.052(2) 0.043(2) 0.036(2) 0.0019(19) 0.0082(18) -0.0073(18)
C9 0.049(2) 0.052(2) 0.040(2) 0.006(2) 0.0127(18) -0.001(2)
C10 0.071(3) 0.049(3) 0.061(3) 0.013(2) 0.021(2) 0.011(2)
C11 0.076(4) 0.076(4) 0.076(4) 0.032(3) 0.008(3) 0.011(3)
C12 0.046(3) 0.095(4) 0.082(4) 0.013(3) 0.003(3) -0.013(3)
C13 0.055(3) 0.052(3) 0.071(3) -0.003(2) 0.013(2) -0.015(2)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N C6 128.0(3)
C7 N H0A 116.0
C6 N H0A 116.0
C6 C1 C2 120.1(4)
C6 C1 H1A 120.0
C2 C1 H1A 120.0
C3 C2 C1 119.8(4)
C3 C2 H2A 120.1
C1 C2 H2A 120.1
C4 C3 C2 120.9(4)
C4 C3 Cl1 119.4(4)
C2 C3 Cl1 119.7(4)
C3 C4 C5 119.6(4)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
C6 C5 C4 120.2(4)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C1 119.5(4)
C5 C6 N 117.6(3)
C1 C6 N 122.7(4)
O C7 N 124.9(4)
O C7 C8 121.7(4)
N C7 C8 113.4(3)
C9 C8 C13 117.1(4)
C9 C8 C7 123.2(4)
C13 C8 C7 119.7(4)
C8 C9 C10 122.2(4)
C8 C9 Cl2 119.6(3)
C10 C9 Cl2 118.3(3)
C11 C10 C9 118.2(5)
C11 C10 H10A 120.9
C9 C10 H10A 120.9
C12 C11 C10 121.7(5)
C12 C11 H11A 119.2
C10 C11 H11A 119.2
C11 C12 C13 119.1(5)
C11 C12 H12A 120.4
C13 C12 H12A 120.4
C12 C13 C8 121.7(5)
C12 C13 Cl3 119.2(4)
C8 C13 Cl3 119.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C7 1.338(5)
N C6 1.417(5)
N H0A 0.8600
O C7 1.216(4)
Cl1 C3 1.737(5)
C1 C6 1.381(5)
C1 C2 1.382(6)
C1 H1A 0.9300
Cl2 C9 1.733(4)
C2 C3 1.365(7)
C2 H2A 0.9300
Cl3 C13 1.732(5)
C3 C4 1.358(7)
C4 C5 1.394(6)
C4 H4A 0.9300
C5 C6 1.366(5)
C5 H5A 0.9300
C7 C8 1.506(5)
C8 C9 1.378(6)
C8 C13 1.389(6)
C9 C10 1.379(6)
C10 C11 1.365(7)
C10 H10A 0.9300
C11 C12 1.363(7)
C11 H11A 0.9300
C12 C13 1.365(7)
C12 H12A 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
_geom_hbond_publ_flag
N H0A O 4_566 0.86 1.97 2.828(4) 176 yes
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 C3 0.8(7)
C1 C2 C3 C4 -1.2(8)
C1 C2 C3 Cl1 178.4(4)
C2 C3 C4 C5 0.2(7)
Cl1 C3 C4 C5 -179.4(4)
C3 C4 C5 C6 1.2(7)
C4 C5 C6 C1 -1.6(6)
C4 C5 C6 N 173.8(4)
C2 C1 C6 C5 0.6(7)
C2 C1 C6 N -174.5(4)
C7 N C6 C5 161.0(4)
C7 N C6 C1 -23.7(6)
C6 N C7 O -5.6(7)
C6 N C7 C8 172.6(3)
O C7 C8 C9 -97.7(5)
N C7 C8 C9 84.1(5)
O C7 C8 C13 82.0(5)
N C7 C8 C13 -96.3(5)
C13 C8 C9 C10 0.3(6)
C7 C8 C9 C10 179.9(4)
C13 C8 C9 Cl2 179.9(3)
C7 C8 C9 Cl2 -0.5(5)
C8 C9 C10 C11 1.2(6)
Cl2 C9 C10 C11 -178.5(4)
C9 C10 C11 C12 -0.8(8)
C10 C11 C12 C13 -1.1(8)
C11 C12 C13 C8 2.6(8)
C11 C12 C13 Cl3 -177.0(4)
C9 C8 C13 C12 -2.2(6)
C7 C8 C13 C12 178.2(4)
C9 C8 C13 Cl3 177.4(3)
C7 C8 C13 Cl3 -2.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3380741
