#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/49/2234951.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_2234951
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Gowda, B. Thimme'
'Sivý, Július'
'Vrábel, Viktor'
'Kožíšek, Jozef'
_publ_section_title
;
 2-Chloro-N-(2-methylphenyl)benzamide
;
_journal_coeditor_code           BT5935
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1936
_journal_paper_doi               10.1107/S1600536812023902
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C14 H12 Cl N O'
_chemical_formula_sum            'C14 H12 Cl N O'
_chemical_formula_weight         245.70
_chemical_name_systematic
;
2-Chloro-N-(2-methylphenyl)benzamide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n 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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.746(3)
_cell_length_b                   6.077(3)
_cell_length_c                   20.797(7)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.49
_cell_volume                     1231.7(8)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2002)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.434
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_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  0.0966
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16249
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2009),
based on expressions derived by Clark & Reid (1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.137
_refine_ls_abs_structure_details 'Flack (1983), 1054 Friedel pairs'
_refine_ls_abs_structure_Flack   0.37(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0680
_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)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1369
_reflns_number_total             2173
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            bt5935.cif
_cod_data_source_block           I
_cod_original_cell_volume        1231.8(8)
_cod_database_code               2234951
_cod_database_fobs_code          2234951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_symmetry_multiplicity
C C1 0.5638(4) 0.6837(8) 0.4527(3) 0.0506(12) Uani d . 1 1
C C2 0.5037(4) 0.5445(10) 0.3997(2) 0.0497(14) Uani d . 1 1
C C3 0.5364(4) 0.5696(9) 0.3373(3) 0.0596(15) Uani d . 1 1
C C4 0.4845(7) 0.4319(12) 0.2916(3) 0.0833(19) Uani d . 1 1
H H4A 0.5099 0.4492 0.2488 0.100 Uiso calc R 1 1
C C5 0.3941(6) 0.2667(12) 0.3087(5) 0.0850(17) Uani d . 1 1
H H5A 0.3587 0.1723 0.2777 0.102 Uiso calc R 1 1
C C6 0.3578(5) 0.2439(10) 0.3713(4) 0.0784(17) Uani d . 1 1
H H6A 0.2968 0.1338 0.3834 0.094 Uiso calc R 1 1
C C7 0.4101(4) 0.3811(10) 0.4159(3) 0.0644(16) Uani d . 1 1
H H7A 0.3830 0.3660 0.4585 0.077 Uiso calc R 1 1
C C8 0.5196(4) 0.9375(9) 0.5395(3) 0.0552(14) Uani d . 1 1
C C9 0.4657(5) 0.9069(10) 0.6004(3) 0.0646(16) Uani d . 1 1
C C10 0.5118(6) 1.0562(13) 0.6480(3) 0.0815(18) Uani d . 1 1
H H10A 0.4756 1.0470 0.6893 0.098 Uiso calc R 1 1
C C11 0.6062(7) 1.2098(13) 0.6351(4) 0.096(3) Uani d . 1 1
H H11A 0.6403 1.2963 0.6684 0.115 Uiso calc R 1 1
C C12 0.6535(5) 1.2420(9) 0.5735(4) 0.0813(19) Uani d . 1 1
H H12A 0.7152 1.3549 0.5647 0.098 Uiso calc R 1 1
C C13 0.6101(4) 1.1096(10) 0.5260(3) 0.0679(17) Uani d . 1 1
H H13A 0.6402 1.1324 0.4841 0.082 Uiso calc R 1 1
C C14 0.3642(5) 0.7289(9) 0.6169(3) 0.0664(16) Uani d . 1 1
H H14C 0.3400 0.7395 0.6615 0.100 Uiso calc R 1 1
H H14B 0.4044 0.5875 0.6086 0.100 Uiso calc R 1 1
H H14A 0.2833 0.7461 0.5910 0.100 Uiso calc R 1 1
N N1 0.4759(4) 0.7929(8) 0.4882(2) 0.0611(12) Uani d D 1 1
H H1 0.3902(14) 0.785(9) 0.479(3) 0.070(17) Uiso d D 1 1
O O1 0.6897(3) 0.6844(6) 0.46020(18) 0.0739(11) Uani d . 1 1
Cl Cl1 0.64973(16) 0.7710(3) 0.31282(10) 0.0971(6) 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
O1 C1 N1 125.1(4)
O1 C1 C2 118.7(4)
N1 C1 C2 116.2(4)
C3 C2 C7 118.0(5)
C3 C2 C1 123.3(5)
C7 C2 C1 118.7(5)
C2 C3 C4 121.0(5)
C2 C3 Cl1 121.1(4)
C4 C3 Cl1 117.9(5)
C3 C4 C5 120.2(6)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C6 C5 C4 119.2(7)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C7 C6 C5 119.9(6)
C7 C6 H6A 120.1
C5 C6 H6A 120.1
C6 C7 C2 121.6(6)
C6 C7 H7A 119.2
C2 C7 H7A 119.2
C9 C8 C13 121.6(5)
C9 C8 N1 118.8(5)
C13 C8 N1 119.6(5)
C8 C9 C10 115.7(6)
C8 C9 C14 123.7(5)
C10 C9 C14 120.6(5)
C11 C10 C9 121.7(6)
C11 C10 H10A 119.2
C9 C10 H10A 119.2
C10 C11 C12 121.1(7)
C10 C11 H11A 119.5
C12 C11 H11A 119.5
C13 C12 C11 119.6(6)
C13 C12 H12A 120.2
C11 C12 H12A 120.2
C12 C13 C8 120.1(6)
C12 C13 H13A 120.0
C8 C13 H13A 120.0
C9 C14 H14C 109.5
C9 C14 H14B 109.5
H14C C14 H14B 109.5
C9 C14 H14A 109.5
H14C C14 H14A 109.5
H14B C14 H14A 109.5
C1 N1 C8 122.0(4)
C1 N1 H1 118(4)
C8 N1 H1 120(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.237(5)
C1 N1 1.311(6)
C1 C2 1.507(7)
C2 C3 1.346(6)
C2 C7 1.389(7)
C3 C4 1.364(7)
C3 Cl1 1.725(6)
C4 C5 1.382(9)
C4 H4A 0.9300
C5 C6 1.356(11)
C5 H5A 0.9300
C6 C7 1.347(8)
C6 H6A 0.9300
C7 H7A 0.9300
C8 C9 1.384(7)
C8 C13 1.396(7)
C8 N1 1.446(6)
C9 C10 1.416(8)
C9 C14 1.506(8)
C10 C11 1.337(10)
C10 H10A 0.9300
C11 C12 1.377(10)
C11 H11A 0.9300
C12 C13 1.342(8)
C12 H12A 0.9300
C13 H13A 0.9300
C14 H14C 0.9600
C14 H14B 0.9600
C14 H14A 0.9600
N1 H1 0.861(2)
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 H1 O1 4_465 0.861(2) 2.000(10) 2.853(5) 171(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
O1 C1 C2 C3 -59.1(7)
N1 C1 C2 C3 122.1(5)
O1 C1 C2 C7 120.7(5)
N1 C1 C2 C7 -58.2(6)
C7 C2 C3 C4 -3.2(8)
C1 C2 C3 C4 176.6(4)
C7 C2 C3 Cl1 179.0(4)
C1 C2 C3 Cl1 -1.2(7)
C2 C3 C4 C5 1.6(8)
Cl1 C3 C4 C5 179.5(5)
C3 C4 C5 C6 0.2(9)
C4 C5 C6 C7 -0.3(9)
C5 C6 C7 C2 -1.4(9)
C3 C2 C7 C6 3.1(8)
C1 C2 C7 C6 -176.7(5)
C13 C8 C9 C10 -2.0(7)
N1 C8 C9 C10 -179.2(4)
C13 C8 C9 C14 177.8(5)
N1 C8 C9 C14 0.6(7)
C8 C9 C10 C11 -2.9(9)
C14 C9 C10 C11 177.2(6)
C9 C10 C11 C12 5.8(10)
C10 C11 C12 C13 -3.6(10)
C11 C12 C13 C8 -1.3(8)
C9 C8 C13 C12 4.2(8)
N1 C8 C13 C12 -178.7(4)
O1 C1 N1 C8 3.0(7)
C2 C1 N1 C8 -178.3(5)
C9 C8 N1 C1 -126.3(5)
C13 C8 N1 C1 56.4(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 192527
