#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222395.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_2222395
loop_
_publ_author_name
'Saeed, Aamer'
'Khera, Rasheed Ahmad'
'Latif, Muhammad'
'Parvez, Masood'
_publ_section_title
;
 4-Chloro-N-cyclohexylbenzamide
;
_journal_coeditor_code           LH2834
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1539
_journal_paper_doi               10.1107/S1600536809021217
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H16 Cl N O'
_chemical_formula_moiety         'C13 H16 Cl N O'
_chemical_formula_sum            'C13 H16 Cl N O'
_chemical_formula_weight         237.72
_chemical_name_systematic        4-Chloro-N-cyclohexylbenzamide
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.13(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.755(14)
_cell_length_b                   5.043(7)
_cell_length_c                   16.818(16)
_cell_measurement_reflns_used    3651
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.9
_cell_volume                     1244(2)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3651
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         3.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.098
_refine_ls_R_factor_gt           0.051
_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)+(0.0665P)²+0.3764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.118
_refine_ls_wR_factor_ref         0.151
_reflns_number_gt                1497
_reflns_number_total             2388
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2834.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222395
_cod_database_fobs_code          2222395
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.77571(5) 0.29595(19) 0.35603(5) 0.0739(3) Uani d . 1 . .
O O1 0.35835(12) 0.8003(3) 0.37556(11) 0.0489(5) Uani d . 1 . .
N N1 0.32675(14) 0.3654(4) 0.38965(14) 0.0491(6) Uani d . 1 . .
H H1 0.3492 0.2036 0.3922 0.059 Uiso calc R 1 . .
C C1 0.48155(15) 0.4944(5) 0.37540(13) 0.0369(6) Uani d . 1 . .
C C2 0.52269(17) 0.2853(5) 0.41805(15) 0.0462(6) Uani d . 1 . .
H H2 0.4884 0.1813 0.4512 0.055 Uiso calc R 1 . .
C C3 0.61349(18) 0.2254(6) 0.41296(16) 0.0529(7) Uani d . 1 . .
H H3 0.6419 0.0831 0.4431 0.063 Uiso calc R 1 . .
C C4 0.66205(17) 0.3746(6) 0.36373(15) 0.0489(7) Uani d . 1 . .
C C5 0.62262(18) 0.5866(6) 0.32108(16) 0.0539(7) Uani d . 1 . .
H H5 0.6569 0.6895 0.2876 0.065 Uiso calc R 1 . .
C C6 0.53255(18) 0.6464(5) 0.32789(15) 0.0474(6) Uani d . 1 . .
H H6 0.5051 0.7938 0.2996 0.057 Uiso calc R 1 . .
C C7 0.38370(16) 0.5666(5) 0.38013(13) 0.0388(6) Uani d . 1 . .
C C8 0.22970(16) 0.3992(5) 0.39603(16) 0.0484(7) Uani d . 1 . .
H H8 0.2181 0.5912 0.4058 0.058 Uiso calc R 1 . .
C C9 0.20142(17) 0.2430(7) 0.46572(16) 0.0564(8) Uani d . 1 . .
H H9A 0.2371 0.3025 0.5157 0.068 Uiso calc R 1 . .
H H9B 0.2142 0.0524 0.4582 0.068 Uiso calc R 1 . .
C C10 0.0997(2) 0.2819(9) 0.4724(2) 0.0789(11) Uani d . 1 . .
H H10A 0.0816 0.1731 0.5171 0.095 Uiso calc R 1 . .
H H10B 0.0881 0.4702 0.4845 0.095 Uiso calc R 1 . .
C C11 0.04290(19) 0.2051(7) 0.3968(2) 0.0735(10) Uani d . 1 . .
H H11A -0.0221 0.2421 0.4022 0.088 Uiso calc R 1 . .
H H11B 0.0494 0.0126 0.3875 0.088 Uiso calc R 1 . .
C C12 0.0718(2) 0.3567(8) 0.3267(2) 0.0819(11) Uani d . 1 . .
H H12A 0.0588 0.5476 0.3333 0.098 Uiso calc R 1 . .
H H12B 0.0360 0.2949 0.2770 0.098 Uiso calc R 1 . .
C C13 0.1742(2) 0.3193(7) 0.31917(18) 0.0699(9) Uani d . 1 . .
H H13A 0.1864 0.1313 0.3072 0.084 Uiso calc R 1 . .
H H13B 0.1920 0.4289 0.2746 0.084 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 . . 123.7(2) ?
C7 N1 H1 . . 118.1 ?
C8 N1 H1 . . 118.1 ?
C2 C1 C6 . . 119.1(2) ?
C2 C1 C7 . . 122.1(2) ?
C6 C1 C7 . . 118.8(2) ?
C1 C2 C3 . . 120.6(2) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.2(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.2(3) ?
C3 C4 Cl1 . . 119.2(2) ?
C5 C4 Cl1 . . 119.6(2) ?
C6 C5 C4 . . 118.8(2) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 C1 . . 121.0(3) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
O1 C7 N1 . . 122.7(2) ?
O1 C7 C1 . . 121.0(2) ?
N1 C7 C1 . . 116.3(2) ?
N1 C8 C9 . . 110.6(2) ?
N1 C8 C13 . . 110.7(2) ?
C9 C8 C13 . . 110.9(2) ?
N1 C8 H8 . . 108.2 ?
C9 C8 H8 . . 108.2 ?
C13 C8 H8 . . 108.2 ?
C8 C9 C10 . . 110.2(2) ?
C8 C9 H9A . . 109.6 ?
C10 C9 H9A . . 109.6 ?
C8 C9 H9B . . 109.6 ?
C10 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
C11 C10 C9 . . 111.7(3) ?
C11 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
C11 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C10 C11 C12 . . 110.8(3) ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C11 C12 C13 . . 111.3(3) ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C8 C13 C12 . . 110.1(3) ?
C8 C13 H13A . . 109.6 ?
C12 C13 H13A . . 109.6 ?
C8 C13 H13B . . 109.6 ?
C12 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 . 1.742(3) ?
O1 C7 . 1.236(3) ?
N1 C7 . 1.338(3) ?
N1 C8 . 1.457(3) ?
N1 H1 . 0.8800 ?
C1 C2 . 1.379(4) ?
C1 C6 . 1.386(3) ?
C1 C7 . 1.499(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.381(4) ?
C5 C6 . 1.379(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C8 C9 . 1.508(4) ?
C8 C13 . 1.510(4) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.530(4) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.496(5) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.505(5) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.541(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
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 1_545 0.88 2.06 2.901(5) 159.9
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.7(4) ?
C7 C1 C2 C3 . . . . -179.3(2) ?
C1 C2 C3 C4 . . . . -1.0(4) ?
C2 C3 C4 C5 . . . . 1.7(4) ?
C2 C3 C4 Cl1 . . . . -178.9(2) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
Cl1 C4 C5 C6 . . . . -180.0(2) ?
C4 C5 C6 C1 . . . . -1.2(4) ?
C2 C1 C6 C5 . . . . 1.8(4) ?
C7 C1 C6 C5 . . . . -179.5(2) ?
C8 N1 C7 O1 . . . . -0.3(4) ?
C8 N1 C7 C1 . . . . 179.5(2) ?
C2 C1 C7 O1 . . . . 145.9(2) ?
C6 C1 C7 O1 . . . . -32.8(3) ?
C2 C1 C7 N1 . . . . -34.0(3) ?
C6 C1 C7 N1 . . . . 147.4(2) ?
C7 N1 C8 C9 . . . . -132.2(3) ?
C7 N1 C8 C13 . . . . 104.5(3) ?
N1 C8 C9 C10 . . . . 179.5(2) ?
C13 C8 C9 C10 . . . . -57.3(3) ?
C8 C9 C10 C11 . . . . 56.9(4) ?
C9 C10 C11 C12 . . . . -56.0(4) ?
C10 C11 C12 C13 . . . . 55.5(4) ?
N1 C8 C13 C12 . . . . -179.8(3) ?
C9 C8 C13 C12 . . . . 57.0(3) ?
C11 C12 C13 C8 . . . . -56.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 195998
