#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/74/2217485.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_2217485
loop_
_publ_author_name
'B. Thimme Gowda'
'Miroslav Tokarčík'
'Jozef Kožíšek'
'B. P. Sowmya'
'Hartmut Fuess '
_publ_section_title
;
 N-(3-Chlorophenyl)benzamide
;
_journal_coeditor_code           DN2311
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o462
_journal_page_last               o462
_journal_paper_doi               10.1107/S1600536808001311
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H10 Cl N O'
_chemical_formula_moiety         'C13 H10 Cl N O'
_chemical_formula_sum            'C13 H10 Cl N O'
_chemical_formula_weight         231.67
_chemical_name_systematic
;
N-(3-Chlorophenyl)benzamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3585(2)
_cell_length_b                   9.7851(2)
_cell_length_c                   25.1419(6)
_cell_measurement_reflns_used    14003
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5001
_cell_measurement_theta_min      2.9999
_cell_volume                     2302.34(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Diamond (Brandenburg, 2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
       PLATON (Spek, 2003) and
       WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.434
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            53566
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         4.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007). Analytical numeric absorption
correction using a multifaceted crystal model (Clark & Reid, 1995).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1639
_reflns_number_total             2252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2311.cif
_cod_data_source_block           I
_cod_database_code               2217485
_cod_database_fobs_code          2217485
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'
'-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
N N1 0.27214(14) 0.48267(13) 0.12047(5) 0.0462(4) Uani d D 1
H H1N 0.2650(19) 0.4004(17) 0.1287(6) 0.055 Uiso d D 1
O O1 0.19225(12) 0.69327(10) 0.14128(5) 0.0565(3) Uani d . 1
Cl Cl1 0.54083(6) 0.81350(6) -0.00120(2) 0.0875(2) Uani d . 1
C C1 0.17675(16) 0.56906(15) 0.14234(6) 0.0405(4) Uani d . 1
C C2 0.05098(15) 0.50735(14) 0.16988(6) 0.0392(4) Uani d . 1
C C3 -0.02405(19) 0.58822(17) 0.20536(7) 0.0546(5) Uani d . 1
H H3 0.0038 0.6784 0.2108 0.065 Uiso calc R 1
C C4 -0.1391(2) 0.53666(19) 0.23252(8) 0.0671(5) Uani d . 1
H H4 -0.1877 0.5916 0.2567 0.081 Uiso calc R 1
C C5 -0.1830(2) 0.4050(2) 0.22432(8) 0.0684(6) Uani d . 1
H H5 -0.2613 0.3706 0.2427 0.082 Uiso calc R 1
C C6 -0.1111(2) 0.32411(18) 0.18890(8) 0.0654(5) Uani d . 1
H H6 -0.1414 0.2349 0.1829 0.079 Uiso calc R 1
C C7 0.00613(18) 0.37454(17) 0.16203(7) 0.0519(4) Uani d . 1
H H7 0.0553 0.3185 0.1384 0.062 Uiso calc R 1
C C8 0.40219(17) 0.52388(15) 0.09631(6) 0.0444(4) Uani d . 1
C C9 0.40661(17) 0.63258(16) 0.06157(6) 0.0471(4) Uani d . 1
H H9 0.3235 0.6796 0.0528 0.056 Uiso calc R 1
C C10 0.53533(19) 0.67062(18) 0.04005(7) 0.0544(5) Uani d . 1
C C11 0.6590(2) 0.6017(2) 0.05099(8) 0.0719(6) Uani d . 1
H H11 0.7453 0.6288 0.0359 0.086 Uiso calc R 1
C C12 0.6527(2) 0.4918(2) 0.08464(10) 0.0808(6) Uani d . 1
H H12 0.7355 0.4428 0.092 0.097 Uiso calc R 1
C C13 0.5255(2) 0.4528(2) 0.10771(8) 0.0657(5) Uani d . 1
H H13 0.523 0.3788 0.1309 0.079 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0440(8) 0.0309(6) 0.0636(9) 0.0007(6) 0.0069(7) 0.0025(6)
O1 0.0570(7) 0.0299(6) 0.0827(8) -0.0007(5) 0.0119(6) 0.0004(5)
Cl1 0.0668(4) 0.0990(5) 0.0968(4) -0.0134(3) 0.0102(3) 0.0423(3)
C1 0.0405(9) 0.0349(8) 0.0462(9) 0.0023(7) -0.0054(7) 0.0006(7)
C2 0.0387(8) 0.0353(8) 0.0437(8) 0.0030(6) -0.0031(7) 0.0027(6)
C3 0.0621(11) 0.0407(9) 0.0609(10) 0.0035(8) 0.0091(9) -0.0026(8)
C4 0.0711(13) 0.0596(11) 0.0707(12) 0.0091(10) 0.0291(11) 0.0013(9)
C5 0.0605(12) 0.0658(12) 0.0789(13) -0.0021(10) 0.0232(11) 0.0136(10)
C6 0.0615(12) 0.0485(10) 0.0862(14) -0.0122(9) 0.0123(11) 0.0001(9)
C7 0.0495(10) 0.0433(9) 0.0628(11) -0.0030(8) 0.0084(8) -0.0081(8)
C8 0.0418(9) 0.0393(8) 0.0521(9) 0.0005(7) 0.0040(7) -0.0044(7)
C9 0.0392(9) 0.0500(9) 0.0520(9) -0.0007(8) -0.0016(8) -0.0003(8)
C10 0.0489(11) 0.0621(11) 0.0521(10) -0.0090(8) 0.0025(8) 0.0038(8)
C11 0.0435(11) 0.0900(14) 0.0824(14) -0.0024(10) 0.0133(10) 0.0107(12)
C12 0.0461(12) 0.0917(15) 0.1046(16) 0.0207(11) 0.0101(11) 0.0216(13)
C13 0.0528(12) 0.0615(11) 0.0827(13) 0.0112(9) 0.0081(10) 0.0170(10)
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 0 '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 0.006 '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
C1 N1 C8 124.41(13)
C1 N1 H1N 116.9(12)
C8 N1 H1N 116.7(12)
O1 C1 N1 122.38(14)
O1 C1 C2 120.33(14)
N1 C1 C2 117.26(13)
C7 C2 C3 118.46(15)
C7 C2 C1 123.66(14)
C3 C2 C1 117.88(13)
C4 C3 C2 120.60(16)
C4 C3 H3 119.7
C2 C3 H3 119.7
C5 C4 C3 120.47(17)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 119.71(17)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C7 120.18(17)
C5 C6 H6 119.9
C7 C6 H6 119.9
C2 C7 C6 120.57(16)
C2 C7 H7 119.7
C6 C7 H7 119.7
C9 C8 C13 119.78(15)
C9 C8 N1 121.12(14)
C13 C8 N1 119.10(14)
C10 C9 C8 119.09(15)
C10 C9 H9 120.5
C8 C9 H9 120.5
C11 C10 C9 122.00(17)
C11 C10 Cl1 119.38(14)
C9 C10 Cl1 118.60(14)
C10 C11 C12 118.36(18)
C10 C11 H11 120.8
C12 C11 H11 120.8
C11 C12 C13 120.98(19)
C11 C12 H12 119.5
C13 C12 H12 119.5
C8 C13 C12 119.76(18)
C8 C13 H13 120.1
C12 C13 H13 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3468(19)
N1 C8 1.419(2)
N1 H1N 0.834(16)
O1 C1 1.2244(17)
Cl1 C10 1.7415(18)
C1 C2 1.493(2)
C2 C7 1.380(2)
C2 C3 1.384(2)
C3 C4 1.371(2)
C3 H3 0.93
C4 C5 1.368(3)
C4 H4 0.93
C5 C6 1.368(3)
C5 H5 0.93
C6 C7 1.380(2)
C6 H6 0.93
C7 H7 0.93
C8 C9 1.377(2)
C8 C13 1.378(2)
C9 C10 1.372(2)
C9 H9 0.93
C10 C11 1.368(3)
C11 C12 1.369(3)
C11 H11 0.93
C12 C13 1.378(3)
C12 H12 0.93
C13 H13 0.93
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 8_655 0.834(16) 2.089(17) 2.8989(17) 163.5(17)
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
C8 N1 C1 O1 3.0(2)
C8 N1 C1 C2 -175.25(14)
O1 C1 C2 C7 163.26(16)
N1 C1 C2 C7 -18.5(2)
O1 C1 C2 C3 -17.0(2)
N1 C1 C2 C3 161.30(14)
C7 C2 C3 C4 0.8(3)
C1 C2 C3 C4 -178.95(15)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C7 0.8(3)
C3 C2 C7 C6 0.2(3)
C1 C2 C7 C6 179.94(16)
C5 C6 C7 C2 -1.0(3)
C1 N1 C8 C9 -45.2(2)
C1 N1 C8 C13 135.30(17)
C13 C8 C9 C10 -1.9(2)
N1 C8 C9 C10 178.61(14)
C8 C9 C10 C11 1.7(3)
C8 C9 C10 Cl1 -176.82(12)
C9 C10 C11 C12 -0.2(3)
Cl1 C10 C11 C12 178.29(17)
C10 C11 C12 C13 -1.1(3)
C9 C8 C13 C12 0.6(3)
N1 C8 C13 C12 -179.87(18)
C11 C12 C13 C8 0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 86512
