#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/88/2218878.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_2218878
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Sowmya, B. P.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2-Chlorophenyl)-2-methylbenzamide
;
_journal_coeditor_code           BG2196
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1421
_journal_paper_doi               10.1107/S1600536808020229
_journal_volume                  64
_journal_year                    2008
_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
;
N-(2-Chlorophenyl)-2-methylbenzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.373(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8881(4)
_cell_length_b                   24.318(2)
_cell_length_c                   10.0562(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      7.28
_cell_volume                     1195.34(17)
_computing_cell_refinement       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_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 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           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2264
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         3.64
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_T_max  0.8780
_exptl_absorpt_correction_T_min  0.6950
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.636
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.494
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.494
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0671
_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)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2438
_refine_ls_wR_factor_ref         0.3326
_reflns_number_gt                1695
_reflns_number_total             2126
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2196.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218878
_cod_database_fobs_code          2218878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.5268(8) 0.58356(18) 0.9109(4) 0.0391(10) Uani d . 1
C C2 0.3925(9) 0.59484(18) 0.7921(5) 0.0435(10) Uani d . 1
C C3 0.4354(12) 0.5627(2) 0.6800(5) 0.0561(13) Uani d . 1
H H3 0.3425 0.5707 0.6014 0.067 Uiso calc R 1
C C4 0.6138(13) 0.5193(2) 0.6847(5) 0.0623(15) Uani d . 1
H H4 0.6438 0.4981 0.6092 0.075 Uiso calc R 1
C C5 0.7482(11) 0.5073(2) 0.8016(5) 0.0576(13) Uani d . 1
H H5 0.8674 0.4776 0.8058 0.069 Uiso calc R 1
C C6 0.7067(10) 0.5393(2) 0.9124(5) 0.0514(12) Uani d . 1
H H6 0.8014 0.5311 0.9904 0.062 Uiso calc R 1
C C7 0.6651(8) 0.63040(19) 1.1158(4) 0.0392(10) Uani d . 1
C C8 0.5627(8) 0.66363(17) 1.2305(4) 0.0377(10) Uani d . 1
C C9 0.6654(10) 0.65413(18) 1.3586(5) 0.0443(11) Uani d . 1
C C10 0.5648(11) 0.6868(2) 1.4611(5) 0.0554(13) Uani d . 1
H H10 0.6293 0.6812 1.5473 0.067 Uiso calc R 1
C C11 0.3720(12) 0.7272(2) 1.4380(6) 0.0632(15) Uani d . 1
H H11 0.3062 0.7481 1.5083 0.076 Uiso calc R 1
C C12 0.2767(11) 0.7365(2) 1.3106(6) 0.0608(14) Uani d . 1
H H12 0.1495 0.7642 1.2945 0.073 Uiso calc R 1
C C13 0.3710(10) 0.7046(2) 1.2075(5) 0.0493(11) Uani d . 1
H H13 0.3054 0.7106 1.1216 0.059 Uiso calc R 1
C C14 0.8698(11) 0.6100(2) 1.3901(5) 0.0549(13) Uani d . 1
H H14A 1.0390 0.6179 1.3461 0.066 Uiso calc R 1
H H14B 0.8010 0.5751 1.3599 0.066 Uiso calc R 1
H H14C 0.9004 0.6086 1.4844 0.066 Uiso calc R 1
N N1 0.4730(7) 0.61465(17) 1.0252(4) 0.0439(9) Uani d . 1
H H1N 0.306(13) 0.623(2) 1.050(5) 0.053 Uiso d . 1
O O1 0.9068(6) 0.61743(16) 1.1044(3) 0.0565(10) Uani d . 1
Cl Cl1 0.1723(3) 0.65063(6) 0.78357(13) 0.0601(6) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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 117.3(4)
C2 C1 N1 120.6(4)
C6 C1 N1 122.1(4)
C1 C2 C3 121.0(4)
C1 C2 Cl1 119.2(3)
C3 C2 Cl1 119.8(4)
C4 C3 C2 120.4(5)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.6(5)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.1(5)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 121.7(4)
C5 C6 H6 119.1
C1 C6 H6 119.1
O1 C7 N1 121.7(4)
O1 C7 C8 122.5(4)
N1 C7 C8 115.8(3)
C13 C8 C9 120.7(4)
C13 C8 C7 119.2(4)
C9 C8 C7 120.0(4)
C10 C9 C8 117.4(5)
C10 C9 C14 119.3(4)
C8 C9 C14 123.2(4)
C11 C10 C9 121.7(5)
C11 C10 H10 119.2
C9 C10 H10 119.2
C12 C11 C10 120.0(5)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 119.6(5)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C8 120.6(5)
C12 C13 H13 119.7
C8 C13 H13 119.7
C9 C14 H14A 109.5
C9 C14 H14B 109.5
H14A C14 H14B 109.5
C9 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 C1 124.7(4)
C7 N1 H1N 113(3)
C1 N1 H1N 122(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(6)
C1 C6 1.390(7)
C1 N1 1.402(5)
C2 C3 1.388(7)
C2 Cl1 1.734(5)
C3 C4 1.369(7)
C3 H3 0.9300
C4 C5 1.375(8)
C4 H4 0.9300
C5 C6 1.374(7)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.229(5)
C7 N1 1.359(5)
C7 C8 1.497(6)
C8 C13 1.386(7)
C8 C9 1.399(6)
C9 C10 1.394(6)
C9 C14 1.499(7)
C10 C11 1.380(8)
C10 H10 0.9300
C11 C12 1.379(8)
C11 H11 0.9300
C12 C13 1.377(7)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 H1N 0.88(6)
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 1_455 0.88(6) 2.03(6) 2.886(5) 163(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
C6 C1 C2 C3 0.5(7)
N1 C1 C2 C3 -177.1(4)
C6 C1 C2 Cl1 -178.4(3)
N1 C1 C2 Cl1 3.9(6)
C1 C2 C3 C4 -0.5(8)
Cl1 C2 C3 C4 178.5(4)
C2 C3 C4 C5 0.7(9)
C3 C4 C5 C6 -1.0(9)
C4 C5 C6 C1 1.1(8)
C2 C1 C6 C5 -0.8(7)
N1 C1 C6 C5 176.8(5)
O1 C7 C8 C13 139.0(5)
N1 C7 C8 C13 -41.8(6)
O1 C7 C8 C9 -39.4(6)
N1 C7 C8 C9 139.8(4)
C13 C8 C9 C10 0.8(6)
C7 C8 C9 C10 179.2(4)
C13 C8 C9 C14 179.1(4)
C7 C8 C9 C14 -2.5(6)
C8 C9 C10 C11 -0.2(7)
C14 C9 C10 C11 -178.6(5)
C9 C10 C11 C12 -0.9(8)
C10 C11 C12 C13 1.3(9)
C11 C12 C13 C8 -0.7(8)
C9 C8 C13 C12 -0.4(7)
C7 C8 C13 C12 -178.8(4)
O1 C7 N1 C1 -1.0(7)
C8 C7 N1 C1 179.8(4)
C2 C1 N1 C7 -141.4(5)
C6 C1 N1 C7 41.1(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 201692
