#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/88/2218834.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_2218834
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Sowmya, B. P.'
'Fuess, Hartmut'
_publ_section_title
;
 2-Chloro-N-(3-chlorophenyl)benzamide
;
_journal_coeditor_code           TK2274
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1300
_journal_paper_doi               10.1107/S1600536808018102
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H9 Cl2 N O'
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11
_chemical_name_systematic
;
2-Chloro-N-(3-chlorophenyl)benzamide
;
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4300(10)
_cell_length_b                   12.209(2)
_cell_length_c                   8.8780(10)
_cell_measurement_reflns_used    1634
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      2.4
_cell_volume                     1238.9(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4926
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.42
_refine_ls_abs_structure_details 'Flack (1983), 387 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.15
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0797P)²+0.0826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                1248
_reflns_number_total             1746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2274.cif
_cod_data_source_block           I
_cod_database_code               2218834
_cod_database_fobs_code          2218834
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
Cl Cl1 0.75422(12) 0.62626(9) -0.0970(2) 0.0776(5) Uani d . 1
Cl Cl2 0.49999(15) 0.21361(13) 0.3455(3) 0.1038(7) Uani d . 1
O O1 0.6539(3) 0.2242(3) -0.0041(3) 0.0597(8) Uani d . 1
N N1 0.7788(3) 0.2603(3) 0.1873(4) 0.0499(9) Uani d . 1
H H1N 0.8049 0.2334 0.2702 0.060 Uiso calc R 1
C C1 0.8275(3) 0.3614(3) 0.1443(5) 0.0437(9) Uani d . 1
C C2 0.7719(3) 0.4339(3) 0.0469(5) 0.0433(9) Uani d . 1
H H2 0.7012 0.4159 0.0014 0.052 Uiso calc R 1
C C3 0.8252(4) 0.5339(3) 0.0200(5) 0.0481(10) Uani d . 1
C C4 0.9300(4) 0.5626(4) 0.0814(5) 0.0559(12) Uani d . 1
H H4 0.9638 0.6301 0.0602 0.067 Uiso calc R 1
C C5 0.9845(4) 0.4894(4) 0.1753(7) 0.0680(14) Uani d . 1
H H5 1.0566 0.5072 0.2173 0.082 Uiso calc R 1
C C6 0.9340(4) 0.3903(4) 0.2082(6) 0.0577(11) Uani d . 1
H H6 0.9713 0.3422 0.2738 0.069 Uiso calc R 1
C C7 0.6971(4) 0.2001(3) 0.1166(5) 0.0444(9) Uani d . 1
C C8 0.6619(3) 0.0962(3) 0.1951(5) 0.0458(9) Uani d . 1
C C9 0.5699(4) 0.0925(4) 0.2959(6) 0.0578(12) Uani d . 1
C C10 0.5336(4) -0.0053(4) 0.3608(7) 0.0766(16) Uani d . 1
H H10 0.4709 -0.0067 0.4275 0.092 Uiso calc R 1
C C11 0.5915(6) -0.0989(4) 0.3252(9) 0.0805(17) Uani d . 1
H H11 0.5689 -0.1646 0.3696 0.097 Uiso calc R 1
C C12 0.6820(6) -0.0983(4) 0.2255(9) 0.090(2) Uani d . 1
H H12 0.7198 -0.1633 0.2007 0.108 Uiso calc R 1
C C13 0.7178(5) -0.0001(4) 0.1608(8) 0.0771(15) Uani d . 1
H H13 0.7803 0.0003 0.0937 0.093 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
Cl1 0.0812(7) 0.0536(6) 0.0981(10) -0.0008(6) -0.0181(7) 0.0268(7)
Cl2 0.1036(10) 0.0798(9) 0.1282(16) 0.0244(8) 0.0548(10) 0.0169(10)
O1 0.0753(19) 0.0604(18) 0.0433(16) -0.0176(15) -0.0119(16) 0.0148(15)
N1 0.059(2) 0.0434(17) 0.047(2) -0.0080(15) -0.0111(17) 0.0101(17)
C1 0.043(2) 0.046(2) 0.042(2) -0.0078(16) 0.0003(19) 0.007(2)
C2 0.044(2) 0.044(2) 0.042(2) -0.0025(17) -0.0062(19) 0.0029(18)
C3 0.054(2) 0.040(2) 0.051(3) 0.0010(18) 0.004(2) 0.0030(19)
C4 0.053(3) 0.060(3) 0.055(3) -0.017(2) -0.001(2) 0.011(2)
C5 0.051(2) 0.078(3) 0.075(4) -0.023(2) -0.008(3) 0.018(3)
C6 0.050(2) 0.068(3) 0.056(3) -0.005(2) -0.011(2) 0.018(2)
C7 0.047(2) 0.046(2) 0.040(2) -0.0003(18) 0.0013(19) 0.0077(19)
C8 0.047(2) 0.045(2) 0.046(2) -0.0003(16) -0.007(2) 0.0032(18)
C9 0.050(2) 0.059(3) 0.064(3) -0.002(2) 0.001(2) 0.014(2)
C10 0.063(3) 0.078(3) 0.089(4) -0.022(3) 0.008(3) 0.029(4)
C11 0.093(4) 0.053(3) 0.096(4) -0.020(3) -0.016(4) 0.027(3)
C12 0.113(5) 0.042(3) 0.116(5) 0.013(3) 0.003(5) 0.011(3)
C13 0.085(3) 0.056(3) 0.090(4) 0.009(2) 0.013(4) 0.002(3)
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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C1 128.9(3)
C7 N1 H1N 115.5
C1 N1 H1N 115.5
C6 C1 C2 119.5(3)
C6 C1 N1 117.3(3)
C2 C1 N1 123.1(3)
C3 C2 C1 117.9(4)
C3 C2 H2 121.1
C1 C2 H2 121.1
C4 C3 C2 123.0(4)
C4 C3 Cl1 118.9(3)
C2 C3 Cl1 118.1(3)
C3 C4 C5 118.4(4)
C3 C4 H4 120.8
C5 C4 H4 120.8
C4 C5 C6 120.8(4)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 120.4(4)
C5 C6 H6 119.8
C1 C6 H6 119.8
O1 C7 N1 124.1(4)
O1 C7 C8 120.3(4)
N1 C7 C8 115.6(3)
C13 C8 C9 118.0(4)
C13 C8 C7 119.8(4)
C9 C8 C7 122.1(4)
C8 C9 C10 121.6(5)
C8 C9 Cl2 119.1(3)
C10 C9 Cl2 119.3(4)
C11 C10 C9 118.8(5)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 121.1(5)
C10 C11 H11 119.4
C12 C11 H11 119.4
C11 C12 C13 119.8(5)
C11 C12 H12 120.1
C13 C12 H12 120.1
C8 C13 C12 120.7(5)
C8 C13 H13 119.7
C12 C13 H13 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.735(4)
Cl2 C9 1.737(5)
O1 C7 1.217(5)
N1 C7 1.344(5)
N1 C1 1.406(5)
N1 H1N 0.8600
C1 C6 1.389(6)
C1 C2 1.391(6)
C2 C3 1.385(5)
C2 H2 0.9300
C3 C4 1.362(6)
C4 C5 1.372(7)
C4 H4 0.9300
C5 C6 1.372(6)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.502(6)
C8 C13 1.372(6)
C8 C9 1.383(6)
C9 C10 1.389(7)
C10 C11 1.358(8)
C10 H10 0.9300
C11 C12 1.362(9)
C11 H11 0.9300
C12 C13 1.390(8)
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
N1 H1N O1 3_655 0.86 2.06 2.880(5) 159
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
C7 N1 C1 C6 -160.3(4)
C7 N1 C1 C2 22.4(7)
C6 C1 C2 C3 -1.1(6)
N1 C1 C2 C3 176.2(4)
C1 C2 C3 C4 1.6(6)
C1 C2 C3 Cl1 -178.2(3)
C2 C3 C4 C5 -0.7(7)
Cl1 C3 C4 C5 179.2(4)
C3 C4 C5 C6 -0.8(8)
C4 C5 C6 C1 1.3(8)
C2 C1 C6 C5 -0.3(7)
N1 C1 C6 C5 -177.7(5)
C1 N1 C7 O1 2.6(7)
C1 N1 C7 C8 -178.6(4)
O1 C7 C8 C13 86.2(6)
N1 C7 C8 C13 -92.5(5)
O1 C7 C8 C9 -90.1(5)
N1 C7 C8 C9 91.1(5)
C13 C8 C9 C10 -0.4(7)
C7 C8 C9 C10 176.0(5)
C13 C8 C9 Cl2 178.2(4)
C7 C8 C9 Cl2 -5.3(6)
C8 C9 C10 C11 0.9(8)
Cl2 C9 C10 C11 -177.8(5)
C9 C10 C11 C12 -1.3(9)
C10 C11 C12 C13 1.2(10)
C9 C8 C13 C12 0.3(9)
C7 C8 C13 C12 -176.2(5)
C11 C12 C13 C8 -0.8(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 307928
