#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222190.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_2222190
loop_
_publ_author_name
'Saeed, Aamer'
'Irfan, Madiha'
'Bolte, Michael'
_publ_section_title
;
 4-Chloro-N-m-tolylbenzamide
;
_journal_coeditor_code           YA2096
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1334
_journal_paper_doi               10.1107/S1600536809018236
_journal_volume                  65
_journal_year                    2009
_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-m-tolylbenzamide
;
_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                 105.415(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9721(14)
_cell_length_b                   10.1922(6)
_cell_length_c                   9.0154(8)
_cell_measurement_reflns_used    10353
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.6
_cell_volume                     1237.67(19)
_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    'PLATON (Spek, 2009)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDSII 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  0.074
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            9469
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.29
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.47
_refine_ls_extinction_coef       0.018(5)
_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   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.066
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1231P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.171
_refine_ls_wR_factor_ref         0.178
_reflns_number_gt                1787
_reflns_number_total             2193
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2096.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1237.67(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222190
_cod_database_fobs_code          2222190
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 0.86033(5) 0.92615(6) 0.74007(9) 0.0588(3) Uani d . 1 . .
O O1 0.41731(13) 0.85570(16) 0.23364(18) 0.0439(5) Uani d . 1 . .
N N1 0.38823(16) 0.72470(18) 0.4215(2) 0.0393(5) Uani d . 1 . .
H H1 0.408(2) 0.702(2) 0.519(3) 0.041(7) Uiso d . 1 . .
C C1 0.44505(17) 0.80750(19) 0.3639(3) 0.0366(5) Uani d . 1 . .
C C11 0.54665(18) 0.83650(19) 0.4646(3) 0.0371(6) Uani d . 1 . .
C C12 0.59229(19) 0.7638(2) 0.5951(3) 0.0435(6) Uani d . 1 . .
H H12 0.5574 0.6930 0.6253 0.052 Uiso calc R 1 . .
C C13 0.68742(19) 0.7929(2) 0.6814(3) 0.0456(6) Uani d . 1 . .
H H13 0.7172 0.7434 0.7711 0.055 Uiso calc R 1 . .
C C14 0.73903(18) 0.8948(2) 0.6362(3) 0.0422(6) Uani d . 1 . .
C C15 0.69544(19) 0.9691(2) 0.5060(3) 0.0413(6) Uani d . 1 . .
H H15 0.7311 1.0387 0.4753 0.050 Uiso calc R 1 . .
C C16 0.6000(2) 0.94034(19) 0.4222(3) 0.0398(6) Uani d . 1 . .
H H16 0.5697 0.9917 0.3343 0.048 Uiso calc R 1 . .
C C21 0.29378(19) 0.6714(2) 0.3444(3) 0.0388(6) Uani d . 1 . .
C C22 0.22613(19) 0.7341(2) 0.2241(3) 0.0404(6) Uani d . 1 . .
H H22 0.2426 0.8166 0.1884 0.049 Uiso calc R 1 . .
C C23 0.13421(19) 0.6770(2) 0.1555(3) 0.0429(6) Uani d . 1 . .
C C24 0.1115(2) 0.5552(2) 0.2080(3) 0.0468(6) Uani d . 1 . .
H H24 0.0499 0.5142 0.1605 0.056 Uiso calc R 1 . .
C C25 0.1784(2) 0.4941(2) 0.3291(3) 0.0488(6) Uani d . 1 . .
H H25 0.1618 0.4118 0.3651 0.059 Uiso calc R 1 . .
C C26 0.2693(2) 0.5508(2) 0.3988(3) 0.0452(6) Uani d . 1 . .
H H26 0.3145 0.5084 0.4826 0.054 Uiso calc R 1 . .
C C27 0.0604(2) 0.7461(3) 0.0252(3) 0.0561(7) Uani d . 1 . .
H H27A 0.0720 0.7202 -0.0732 0.084 Uiso calc R 1 . .
H H27B 0.0686 0.8413 0.0383 0.084 Uiso calc R 1 . .
H H27C -0.0073 0.7216 0.0264 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
C1 N1 C21 . . 127.7(2) ?
C1 N1 H1 . . 119.2(18) ?
C21 N1 H1 . . 112.9(18) ?
O1 C1 N1 . . 123.0(2) ?
O1 C1 C11 . . 120.3(2) ?
N1 C1 C11 . . 116.7(2) ?
C12 C11 C16 . . 118.3(2) ?
C12 C11 C1 . . 123.7(2) ?
C16 C11 C1 . . 118.0(2) ?
C13 C12 C11 . . 121.1(2) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 119.5(2) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.6(2) ?
C13 C14 Cl1 . . 119.28(19) ?
C15 C14 Cl1 . . 120.04(19) ?
C16 C15 C14 . . 119.3(2) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C11 . . 121.2(2) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
C22 C21 C26 . . 119.9(2) ?
C22 C21 N1 . . 123.7(2) ?
C26 C21 N1 . . 116.4(2) ?
C21 C22 C23 . . 120.6(2) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
C24 C23 C22 . . 119.1(2) ?
C24 C23 C27 . . 120.5(2) ?
C22 C23 C27 . . 120.4(2) ?
C25 C24 C23 . . 120.1(2) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 121.1(2) ?
C24 C25 H25 . . 119.5 ?
C26 C25 H25 . . 119.5 ?
C25 C26 C21 . . 119.2(2) ?
C25 C26 H26 . . 120.4 ?
C21 C26 H26 . . 120.4 ?
C23 C27 H27A . . 109.5 ?
C23 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C23 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
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 C14 . 1.734(3) ?
O1 C1 . 1.236(3) ?
N1 C1 . 1.353(3) ?
N1 C21 . 1.426(3) ?
N1 H1 . 0.88(3) ?
C1 C11 . 1.497(3) ?
C11 C12 . 1.393(3) ?
C11 C16 . 1.404(3) ?
C12 C13 . 1.382(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.393(3) ?
C15 C16 . 1.378(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.390(3) ?
C21 C26 . 1.398(3) ?
C22 C23 . 1.396(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.394(3) ?
C23 C27 . 1.515(4) ?
C24 C25 . 1.383(4) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.385(4) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
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_576 0.88(3) 1.99(3) 2.854(3) 166(3)
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
C21 N1 C1 O1 . . . . 5.0(4) ?
C21 N1 C1 C11 . . . . -173.24(19) ?
O1 C1 C11 C12 . . . . -164.2(2) ?
N1 C1 C11 C12 . . . . 14.2(3) ?
O1 C1 C11 C16 . . . . 13.8(3) ?
N1 C1 C11 C16 . . . . -167.84(19) ?
C16 C11 C12 C13 . . . . 0.2(4) ?
C1 C11 C12 C13 . . . . 178.2(2) ?
C11 C12 C13 C14 . . . . -1.0(4) ?
C12 C13 C14 C15 . . . . 0.9(4) ?
C12 C13 C14 Cl1 . . . . -177.17(19) ?
C13 C14 C15 C16 . . . . 0.1(4) ?
Cl1 C14 C15 C16 . . . . 178.14(18) ?
C14 C15 C16 C11 . . . . -1.0(4) ?
C12 C11 C16 C15 . . . . 0.8(3) ?
C1 C11 C16 C15 . . . . -177.3(2) ?
C1 N1 C21 C22 . . . . -28.5(4) ?
C1 N1 C21 C26 . . . . 153.4(2) ?
C26 C21 C22 C23 . . . . -0.9(4) ?
N1 C21 C22 C23 . . . . -179.0(2) ?
C21 C22 C23 C24 . . . . -0.7(4) ?
C21 C22 C23 C27 . . . . 179.5(2) ?
C22 C23 C24 C25 . . . . 1.6(4) ?
C27 C23 C24 C25 . . . . -178.6(3) ?
C23 C24 C25 C26 . . . . -1.0(4) ?
C24 C25 C26 C21 . . . . -0.6(4) ?
C22 C21 C26 C25 . . . . 1.5(4) ?
N1 C21 C26 C25 . . . . 179.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 309335
