#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/21/2232175.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_2232175
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Fronc, Marek'
'Gowda, B. Thimme'
'Kožíšek, Jozef'
_publ_section_title
;
 4-Chloro-N-(3-methylphenyl)benzamide
;
_journal_coeditor_code           BT5661
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2903
_journal_paper_doi               10.1107/S1600536811040864
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H12 Cl N O'
_chemical_formula_moiety         'C14 H12 Cl N O'
_chemical_formula_sum            'C14 H12 Cl N O'
_chemical_formula_weight         245.70
_chemical_name_systematic
;
4-Chloro-N-(3-methylphenyl)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                 92.893(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4379(9)
_cell_length_b                   10.2493(11)
_cell_length_c                   9.2600(7)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4074
_cell_measurement_theta_min      3.3772
_cell_volume                     1273.75(19)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       'ω scans'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17187
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived
from Clark & Reid (1995)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.808
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0403
_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)+(0.0699P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                1299
_reflns_number_total             2156
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5661.cif
_cod_data_source_block           I
_cod_original_cell_volume        1273.74(19)
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232175
_cod_database_fobs_code          2232175
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
C C1 0.44789(14) 0.3375(2) -0.05692(18) 0.0570(5) Uani d . 1 1
C C2 0.40134(16) 0.2716(2) 0.0505(2) 0.0749(6) Uani d . 1 1
H H2A 0.4350 0.2045 0.0999 0.090 Uiso calc R 1 1
C C3 0.30600(17) 0.3031(3) 0.0860(3) 0.0850(7) Uani d . 1 1
H H3A 0.2759 0.2590 0.1600 0.102 Uiso calc R 1 1
C C4 0.25583(15) 0.4008(3) 0.0105(3) 0.0746(6) Uani d . 1 1
C C5 0.30042(16) 0.4691(2) -0.0950(2) 0.0715(6) Uani d . 1 1
H H5A 0.2665 0.5361 -0.1441 0.086 Uiso calc R 1 1
C C6 0.39659(15) 0.4374(2) -0.1280(2) 0.0651(6) Uani d . 1 1
H H6A 0.4274 0.4841 -0.1994 0.078 Uiso calc R 1 1
C C7 0.54954(14) 0.3041(2) -0.10552(19) 0.0587(5) Uani d . 1 1
C C8 0.70086(15) 0.1721(2) -0.0475(2) 0.0636(6) Uani d . 1 1
C C9 0.76789(15) 0.2328(2) -0.1344(2) 0.0695(6) Uani d . 1 1
H H9A 0.7512 0.3126 -0.1768 0.083 Uiso calc R 1 1
C C10 0.85939(16) 0.1769(3) -0.1594(2) 0.0806(7) Uani d . 1 1
C C11 0.88194(19) 0.0584(3) -0.0961(3) 0.0932(8) Uani d . 1 1
H H11A 0.9423 0.0185 -0.1139 0.112 Uiso calc R 1 1
C C12 0.8172(2) -0.0028(3) -0.0066(3) 0.0966(8) Uani d . 1 1
H H12A 0.8347 -0.0820 0.0366 0.116 Uiso calc R 1 1
C C13 0.72518(18) 0.0546(3) 0.0188(2) 0.0811(7) Uani d . 1 1
H H13A 0.6812 0.0144 0.0793 0.097 Uiso calc R 1 1
C C14 0.93185(19) 0.2429(3) -0.2533(3) 0.1117(10) Uani d . 1 1
H H14C 0.9906 0.1900 -0.2584 0.134 Uiso calc R 1 1
H H14B 0.9496 0.3265 -0.2129 0.134 Uiso calc R 1 1
H H14A 0.9018 0.2544 -0.3487 0.134 Uiso calc R 1 1
N N1 0.60639(12) 0.22675(17) -0.01846(16) 0.0636(5) Uani d . 1 1
H H1A 0.5833 0.2081 0.0640 0.076 Uiso calc R 1 1
O O1 0.57677(10) 0.34502(16) -0.22211(13) 0.0762(5) Uani d . 1 1
Cl Cl1 0.13343(4) 0.43547(8) 0.04942(9) 0.1151(4) Uani d . 1 1
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
C2 C1 C6 118.24(19)
C2 C1 C7 123.92(19)
C6 C1 C7 117.79(17)
C3 C2 C1 121.3(2)
C3 C2 H2A 119.4
C1 C2 H2A 119.4
C2 C3 C4 119.1(2)
C2 C3 H3A 120.4
C4 C3 H3A 120.4
C5 C4 C3 121.0(2)
C5 C4 Cl1 119.86(19)
C3 C4 Cl1 119.17(18)
C4 C5 C6 119.1(2)
C4 C5 H5A 120.4
C6 C5 H5A 120.4
C5 C6 C1 121.23(19)
C5 C6 H6A 119.4
C1 C6 H6A 119.4
O1 C7 N1 122.88(18)
O1 C7 C1 120.08(17)
N1 C7 C1 117.03(16)
C13 C8 C9 120.2(2)
C13 C8 N1 116.8(2)
C9 C8 N1 123.0(2)
C8 C9 C10 121.3(2)
C8 C9 H9A 119.4
C10 C9 H9A 119.4
C11 C10 C9 118.2(2)
C11 C10 C14 120.7(2)
C9 C10 C14 121.2(3)
C10 C11 C12 121.6(2)
C10 C11 H11A 119.2
C12 C11 H11A 119.2
C11 C12 C13 119.9(3)
C11 C12 H12A 120.0
C13 C12 H12A 120.0
C8 C13 C12 118.8(2)
C8 C13 H13A 120.6
C12 C13 H13A 120.6
C10 C14 H14C 109.5
C10 C14 H14B 109.5
H14C C14 H14B 109.5
C10 C14 H14A 109.5
H14C C14 H14A 109.5
H14B C14 H14A 109.5
C7 N1 C8 127.20(16)
C7 N1 H1A 116.4
C8 N1 H1A 116.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(3)
C1 C6 1.382(3)
C1 C7 1.499(3)
C2 C3 1.377(3)
C2 H2A 0.9300
C3 C4 1.378(3)
C3 H3A 0.9300
C4 C5 1.365(3)
C4 Cl1 1.738(2)
C5 C6 1.381(3)
C5 H5A 0.9300
C6 H6A 0.9300
C7 O1 1.231(2)
C7 N1 1.342(2)
C8 C13 1.383(3)
C8 C9 1.386(3)
C8 N1 1.426(3)
C9 C10 1.387(3)
C9 H9A 0.9300
C10 C11 1.375(4)
C10 C14 1.499(4)
C11 C12 1.382(4)
C11 H11A 0.9300
C12 C13 1.400(4)
C12 H12A 0.9300
C13 H13A 0.9300
C14 H14C 0.9600
C14 H14B 0.9600
C14 H14A 0.9600
N1 H1A 0.8600
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 H1A O1 4_566 0.86 2.06 2.888(2) 161.2
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 0.4(3)
C7 C1 C2 C3 -177.07(19)
C1 C2 C3 C4 1.3(4)
C2 C3 C4 C5 -2.2(4)
C2 C3 C4 Cl1 176.97(18)
C3 C4 C5 C6 1.3(3)
Cl1 C4 C5 C6 -177.83(15)
C4 C5 C6 C1 0.5(3)
C2 C1 C6 C5 -1.3(3)
C7 C1 C6 C5 176.33(17)
C2 C1 C7 O1 162.80(19)
C6 C1 C7 O1 -14.7(3)
C2 C1 C7 N1 -15.7(3)
C6 C1 C7 N1 166.77(17)
C13 C8 C9 C10 1.3(3)
N1 C8 C9 C10 179.60(17)
C8 C9 C10 C11 0.4(3)
C8 C9 C10 C14 -179.9(2)
C9 C10 C11 C12 -1.7(3)
C14 C10 C11 C12 178.6(2)
C10 C11 C12 C13 1.4(4)
C9 C8 C13 C12 -1.6(3)
N1 C8 C13 C12 179.96(18)
C11 C12 C13 C8 0.3(3)
O1 C7 N1 C8 -4.9(3)
C1 C7 N1 C8 173.59(17)
C13 C8 N1 C7 -151.2(2)
C9 C8 N1 C7 30.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 309335
