#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228321.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228321
loop_
_publ_author_name
'Raza, Abdul Rauf'
'Nisar, Bushra'
'Tahir, M. Nawaz'
'Shamshad, Sumaira'
_publ_section_title
;
 N-(3-Chlorophenyl)-2-hydroxybenzamide
;
_journal_coeditor_code           GK2313
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3100
_journal_paper_doi               10.1107/S1600536810045046
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H10 Cl N O2'
_chemical_formula_moiety         'C13 H10 Cl N O2'
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.67
_chemical_name_systematic
;
N-(3-Chlorophenyl)-2-hydroxybenzamide
;
_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
_cell_angle_beta                 98.808(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4638(5)
_cell_length_b                   11.9019(4)
_cell_length_c                   7.1764(2)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      1.53
_cell_volume                     1136.42(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10332
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.338
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0427
_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)+(0.0498P)²+0.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1827
_reflns_number_total             2806
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2313.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228321
_cod_database_fobs_code          2228321
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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 0.95784(4) -0.09691(5) 0.80925(10) 0.0858(3) Uani d . 1 . .
O O1 0.49322(9) -0.04858(10) 0.79519(19) 0.0502(3) Uani d . 1 . .
H H1 0.4719(16) -0.1099(18) 0.840(3) 0.071(7) Uiso d . 1 . .
O O2 0.55912(9) 0.26044(9) 0.57224(17) 0.0480(3) Uani d . 1 . .
N N1 0.61841(11) 0.09050(11) 0.6738(2) 0.0414(3) Uani d . 1 . .
H H1A 0.5995(13) 0.0264(16) 0.714(2) 0.050 Uiso d . 1 . .
C C1 0.44202(12) 0.13109(13) 0.6707(2) 0.0365(4) Uani d . 1 . .
C C2 0.41952(12) 0.02934(13) 0.7532(2) 0.0389(4) Uani d . 1 . .
C C3 0.32279(13) 0.00851(15) 0.7912(2) 0.0461(4) Uani d . 1 . .
H H3 0.3090 -0.0579 0.8505 0.055 Uiso calc R 1 . .
C C4 0.24770(14) 0.08575(16) 0.7414(3) 0.0522(5) Uani d . 1 . .
H H4 0.1834 0.0714 0.7677 0.063 Uiso calc R 1 . .
C C5 0.26700(13) 0.18469(15) 0.6526(3) 0.0536(5) Uani d . 1 . .
H H5 0.2155 0.2358 0.6160 0.064 Uiso calc R 1 . .
C C6 0.36320(13) 0.20707(14) 0.6187(2) 0.0452(4) Uani d . 1 . .
H H6 0.3760 0.2741 0.5600 0.054 Uiso calc R 1 . .
C C7 0.54346(12) 0.16594(13) 0.6345(2) 0.0367(4) Uani d . 1 . .
C C8 0.72051(13) 0.10029(13) 0.6548(2) 0.0390(4) Uani d . 1 . .
C C9 0.78234(13) 0.01425(15) 0.7347(2) 0.0456(4) Uani d . 1 . .
H H9 0.7562 -0.0433 0.8002 0.055 Uiso calc R 1 . .
C C10 0.88287(14) 0.01472(16) 0.7165(3) 0.0522(5) Uani d . 1 . .
C C11 0.92390(15) 0.09982(18) 0.6235(3) 0.0589(5) Uani d . 1 . .
H H11 0.9920 0.1001 0.6141 0.071 Uiso calc R 1 . .
C C12 0.86155(14) 0.18490(16) 0.5443(3) 0.0547(5) Uani d . 1 . .
H H12 0.8883 0.2427 0.4802 0.066 Uiso calc R 1 . .
C C13 0.76052(13) 0.18621(14) 0.5579(2) 0.0467(4) Uani d . 1 . .
H H13 0.7196 0.2439 0.5030 0.056 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 112.7(14) ?
C7 N1 C8 . . 129.47(14) ?
C7 N1 H1A . . 114.0(12) ?
C8 N1 H1A . . 116.5(12) ?
C6 C1 C2 . . 117.81(15) ?
C6 C1 C7 . . 116.86(14) ?
C2 C1 C7 . . 125.34(14) ?
O1 C2 C3 . . 120.55(15) ?
O1 C2 C1 . . 119.08(15) ?
C3 C2 C1 . . 120.37(15) ?
C4 C3 C2 . . 120.22(16) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.50(17) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 119.56(17) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 121.45(16) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
O2 C7 N1 . . 121.10(15) ?
O2 C7 C1 . . 121.81(14) ?
N1 C7 C1 . . 117.09(14) ?
C9 C8 C13 . . 119.72(16) ?
C9 C8 N1 . . 115.60(14) ?
C13 C8 N1 . . 124.65(15) ?
C10 C9 C8 . . 119.55(17) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C11 C10 C9 . . 121.47(18) ?
C11 C10 Cl1 . . 119.74(15) ?
C9 C10 Cl1 . . 118.78(15) ?
C10 C11 C12 . . 118.42(18) ?
C10 C11 H11 . . 120.8 ?
C12 C11 H11 . . 120.8 ?
C13 C12 C11 . . 121.54(18) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C12 C13 C8 . . 119.29(17) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
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 C10 . 1.7381(19) ?
O1 C2 . 1.3579(19) ?
O1 H1 . 0.87(2) ?
O2 C7 . 1.2400(19) ?
N1 C7 . 1.348(2) ?
N1 C8 . 1.407(2) ?
N1 H1A . 0.866(18) ?
C1 C6 . 1.401(2) ?
C1 C2 . 1.401(2) ?
C1 C7 . 1.488(2) ?
C2 C3 . 1.393(2) ?
C3 C4 . 1.373(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.383(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.387(2) ?
C8 C13 . 1.391(2) ?
C9 C10 . 1.380(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.375(3) ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.379(2) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
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
_geom_hbond_publ_flag
O1 H1 O2 2_646 0.88(2) 1.73(2) 2.6016(18) 173(2) yes
N1 H1A O1 . 0.88(2) 1.85(2) 2.606(2) 143.4(18) yes
C13 H13 O2 . 0.93 2.30 2.869(2) 119 yes
C6 H6 Cg1 4_554 0.93 2.89 3.675(2) 143 yes
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
C8 N1 C7 O2 . . . . -0.4(3) no
C8 N1 C7 C1 . . . . -179.66(16) no
C7 N1 C8 C9 . . . . 170.31(17) no
C7 N1 C8 C13 . . . . -11.9(3) no
C6 C1 C2 O1 . . . . 176.28(15) no
C6 C1 C2 C3 . . . . -3.6(2) no
C7 C1 C2 O1 . . . . -4.1(2) no
C7 C1 C2 C3 . . . . 176.04(16) no
C2 C1 C6 C5 . . . . 2.0(3) no
C7 C1 C6 C5 . . . . -177.67(17) no
C2 C1 C7 O2 . . . . -175.16(15) no
C2 C1 C7 N1 . . . . 4.1(2) no
C6 C1 C7 O2 . . . . 4.5(2) no
C6 C1 C7 N1 . . . . -176.25(15) no
O1 C2 C3 C4 . . . . -177.32(17) no
C1 C2 C3 C4 . . . . 2.6(3) no
C2 C3 C4 C5 . . . . 0.2(3) no
C3 C4 C5 C6 . . . . -1.8(3) no
C4 C5 C6 C1 . . . . 0.7(3) no
N1 C8 C9 C10 . . . . 177.43(18) no
C13 C8 C9 C10 . . . . -0.4(3) no
N1 C8 C13 C12 . . . . -178.15(19) no
C9 C8 C13 C12 . . . . -0.5(3) no
C8 C9 C10 Cl1 . . . . -177.25(16) no
C8 C9 C10 C11 . . . . 1.4(3) no
Cl1 C10 C11 C12 . . . . 177.29(17) no
C9 C10 C11 C12 . . . . -1.3(3) no
C10 C11 C12 C13 . . . . 0.4(3) no
C11 C12 C13 C8 . . . . 0.5(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 420152
