#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222099.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_2222099
loop_
_publ_author_name
'Khawar Rauf, M.'
'Bolte, Michael'
'Badshah, Amin'
_publ_section_title
;
 3-Chloro-N-cyclohexylbenzamide
;
_journal_coeditor_code           LH2817
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1265
_journal_paper_doi               10.1107/S1600536809017012
_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_common            3-chloro-N-cyclohexylbenzamide
_chemical_name_systematic
;
3-Chloro-N-cyclohexylbenzamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4963(6)
_cell_length_b                   11.4891(7)
_cell_length_c                   12.5318(11)
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.4
_cell_volume                     1223.29(16)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6758
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.8975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[MULABS (Spek, 2003; Blessing, 1995)]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.172
_refine_ls_abs_structure_details 'Flack (1983), 1128 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                2429
_reflns_number_total             2737
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2817.cif
_cod_data_source_block           I
_cod_database_code               2222099
_cod_database_fobs_code          2222099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.70767(6) 1.17100(4) 0.53982(4) 0.04673(13) Uani d . 1 . .
C C1 0.54914(14) 0.73267(12) 0.53979(11) 0.0203(3) Uani d . 1 . .
O O1 0.43572(10) 0.67397(9) 0.56950(7) 0.0245(2) Uani d . 1 . .
N N1 0.63351(13) 0.70808(10) 0.45221(9) 0.0233(2) Uani d . 1 . .
H H1 0.720(2) 0.7470(16) 0.4421(13) 0.028(4) Uiso d . 1 . .
C C11 0.59541(13) 0.84022(13) 0.60027(10) 0.0208(3) Uani d . 1 . .
C C12 0.63710(15) 0.94177(12) 0.54747(11) 0.0233(3) Uani d . 1 . .
H H12 0.6474 0.9425 0.4720 0.028 Uiso calc R 1 . .
C C13 0.66355(15) 1.04213(13) 0.60606(11) 0.0260(3) Uani d . 1 . .
C C14 0.65300(16) 1.04247(14) 0.71660(12) 0.0289(3) Uani d . 1 . .
H H14 0.6727 1.1117 0.7558 0.035 Uiso calc R 1 . .
C C15 0.61351(17) 0.94075(15) 0.76869(12) 0.0300(3) Uani d . 1 . .
H H15 0.6069 0.9399 0.8444 0.036 Uiso calc R 1 . .
C C16 0.58335(14) 0.83946(14) 0.71154(11) 0.0253(3) Uani d . 1 . .
H H16 0.5547 0.7701 0.7479 0.030 Uiso calc R 1 . .
C C21 0.59346(14) 0.61160(13) 0.38088(11) 0.0218(3) Uani d . 1 . .
H H21 0.4778 0.5966 0.3868 0.026 Uiso calc R 1 . .
C C22 0.62972(17) 0.64688(13) 0.26615(11) 0.0274(3) Uani d . 1 . .
H H22A 0.7431 0.6654 0.2594 0.033 Uiso calc R 1 . .
H H22B 0.5690 0.7176 0.2476 0.033 Uiso calc R 1 . .
C C23 0.58727(17) 0.54859(16) 0.18917(12) 0.0334(4) Uani d . 1 . .
H H23A 0.4722 0.5353 0.1911 0.040 Uiso calc R 1 . .
H H23B 0.6161 0.5717 0.1156 0.040 Uiso calc R 1 . .
C C24 0.67181(18) 0.43660(15) 0.21786(13) 0.0340(3) Uani d . 1 . .
H H24A 0.7865 0.4471 0.2080 0.041 Uiso calc R 1 . .
H H24B 0.6367 0.3735 0.1696 0.041 Uiso calc R 1 . .
C C25 0.6385(2) 0.40235(15) 0.33291(14) 0.0373(4) Uani d . 1 . .
H H25A 0.7005 0.3322 0.3511 0.045 Uiso calc R 1 . .
H H25B 0.5255 0.3827 0.3405 0.045 Uiso calc R 1 . .
C C26 0.68006(17) 0.50066(13) 0.41084(12) 0.0292(3) Uani d . 1 . .
H H26A 0.6508 0.4774 0.4843 0.035 Uiso calc R 1 . .
H H26B 0.7950 0.5148 0.4092 0.035 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
O1 C1 N1 . . 123.32(13) ?
O1 C1 C11 . . 120.12(11) ?
N1 C1 C11 . . 116.52(11) ?
C1 N1 C21 . . 122.34(11) ?
C1 N1 H1 . . 117.6(11) ?
C21 N1 H1 . . 119.8(11) ?
C12 C11 C16 . . 119.98(13) ?
C12 C11 C1 . . 121.20(11) ?
C16 C11 C1 . . 118.62(13) ?
C13 C12 C11 . . 119.25(12) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 121.38(14) ?
C12 C13 Cl1 . . 119.39(11) ?
C14 C13 Cl1 . . 119.22(12) ?
C15 C14 C13 . . 119.04(14) ?
C15 C14 H14 . . 120.5 ?
C13 C14 H14 . . 120.5 ?
C14 C15 C16 . . 120.66(13) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 119.67(15) ?
C15 C16 H16 . . 120.2 ?
C11 C16 H16 . . 120.2 ?
N1 C21 C26 . . 111.83(11) ?
N1 C21 C22 . . 109.11(11) ?
C26 C21 C22 . . 110.99(11) ?
N1 C21 H21 . . 108.3 ?
C26 C21 H21 . . 108.3 ?
C22 C21 H21 . . 108.3 ?
C21 C22 C23 . . 110.54(13) ?
C21 C22 H22A . . 109.5 ?
C23 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
C23 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
C24 C23 C22 . . 111.43(12) ?
C24 C23 H23A . . 109.3 ?
C22 C23 H23A . . 109.3 ?
C24 C23 H23B . . 109.3 ?
C22 C23 H23B . . 109.3 ?
H23A C23 H23B . . 108.0 ?
C23 C24 C25 . . 110.85(13) ?
C23 C24 H24A . . 109.5 ?
C25 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
C25 C24 H24B . . 109.5 ?
H24A C24 H24B . . 108.1 ?
C24 C25 C26 . . 111.71(13) ?
C24 C25 H25A . . 109.3 ?
C26 C25 H25A . . 109.3 ?
C24 C25 H25B . . 109.3 ?
C26 C25 H25B . . 109.3 ?
H25A C25 H25B . . 107.9 ?
C21 C26 C25 . . 110.41(13) ?
C21 C26 H26A . . 109.6 ?
C25 C26 H26A . . 109.6 ?
C21 C26 H26B . . 109.6 ?
C25 C26 H26B . . 109.6 ?
H26A C26 H26B . . 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 C13 . 1.7383(16) ?
C1 O1 . 1.2337(16) ?
C1 N1 . 1.3410(17) ?
C1 C11 . 1.5020(18) ?
N1 C21 . 1.4641(17) ?
N1 H1 . 0.868(18) ?
C11 C12 . 1.387(2) ?
C11 C16 . 1.3982(18) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.388(2) ?
C14 C15 . 1.380(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.390(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C26 . 1.519(2) ?
C21 C22 . 1.5253(19) ?
C21 H21 . 1.0000 ?
C22 C23 . 1.528(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.517(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.521(2) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 C26 . 1.534(2) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 H26A . 0.9900 ?
C26 H26B . 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 4_566 0.868(18) 2.052(18) 2.9161(15) 173.3(16)
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
O1 C1 N1 C21 . . . . 2.9(2) ?
C11 C1 N1 C21 . . . . -174.88(11) ?
O1 C1 C11 C12 . . . . -137.24(12) ?
N1 C1 C11 C12 . . . . 40.62(17) ?
O1 C1 C11 C16 . . . . 37.55(17) ?
N1 C1 C11 C16 . . . . -144.60(12) ?
C16 C11 C12 C13 . . . . -1.17(19) ?
C1 C11 C12 C13 . . . . 173.54(11) ?
C11 C12 C13 C14 . . . . 1.6(2) ?
C11 C12 C13 Cl1 . . . . -177.30(9) ?
C12 C13 C14 C15 . . . . -0.8(2) ?
Cl1 C13 C14 C15 . . . . 178.16(10) ?
C13 C14 C15 C16 . . . . -0.5(2) ?
C14 C15 C16 C11 . . . . 0.9(2) ?
C12 C11 C16 C15 . . . . -0.08(19) ?
C1 C11 C16 C15 . . . . -174.93(12) ?
C1 N1 C21 C26 . . . . -92.52(14) ?
C1 N1 C21 C22 . . . . 144.31(12) ?
N1 C21 C22 C23 . . . . -179.27(11) ?
C26 C21 C22 C23 . . . . 57.06(15) ?
C21 C22 C23 C24 . . . . -56.47(16) ?
C22 C23 C24 C25 . . . . 55.47(17) ?
C23 C24 C25 C26 . . . . -55.16(18) ?
N1 C21 C26 C25 . . . . -178.62(12) ?
C22 C21 C26 C25 . . . . -56.52(15) ?
C24 C25 C26 C21 . . . . 55.74(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 271269
