##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     ?
_journal_date_recd_electronic     2011-07-25
_journal_date_accepted     2011-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      9
_journal_page_first     o2253
_journal_page_last     o2253
_journal_paper_category     QO
_journal_coeditor_code     TK2771
_publ_contact_author
;
Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com'
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 914'
_publ_section_title
;
2-Hydroxy-N-(4-methylphenyl)benzamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Raza, Abdul Rauf'
;
Department of Chemistry
University of Sargodha
Sargodha
Pakistan
;
    'Bushra Nisar'
;
Department of Chemistry
University of Sargodha
Sargodha
Pakistan
;
    'Tahir, M. Nawaz'
;
Department of Physics
University of Sargodha
Sargodha
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Hydroxy-N-(4-methylphenyl)benzamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H13 N O2'
_chemical_formula_sum     'C14 H13 N O2'
_chemical_formula_iupac     'C14 H13 N O2'
_chemical_formula_weight     227.25
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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
_cell_length_a     19.4067(17)
_cell_length_b     4.9122(5)
_cell_length_c     12.7261(11)
_cell_angle_alpha     90
_cell_angle_beta     104.793(4)
_cell_angle_gamma     90
_cell_volume     1172.96(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1243
_cell_measurement_theta_min     1.09
_cell_measurement_theta_max     27.86
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.287
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.979
_exptl_absorpt_correction_T_max     0.988
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.6
_diffrn_reflns_number     10416
_diffrn_reflns_av_R_equivalents     0.0604
_diffrn_reflns_av_sigmaI/netI     0.0874
_diffrn_reflns_theta_min     1.09
_diffrn_reflns_theta_max     27.86
_diffrn_reflns_theta_full     27.86
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2771
_reflns_number_gt     1243
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1557
_refine_ls_R_factor_gt     0.0586
_refine_ls_wR_factor_gt     0.1218
_refine_ls_wR_factor_ref     0.1588
_refine_ls_goodness_of_fit_ref     0.964
_refine_ls_restrained_S_all     0.964
_refine_ls_number_reflns     2771
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0648P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.189
_refine_diff_density_min     -0.164
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.29367(9) -0.2157(4) 0.22720(13) 0.0599(7) Uani . . 1.000 . -16
    O O2 0.29429(9) -0.0348(3) -0.09273(12) 0.0598(7) Uani . . 1.000 . -16
    N N1 0.24804(9) 0.0722(4) 0.04697(14) 0.0438(7) Uani . . 1.000 . -16
    C C1 0.33925(11) -0.2782(5) 0.07185(18) 0.0407(8) Uani . . 1.000 . -16
    C C2 0.33876(12) -0.3489(5) 0.17802(18) 0.0438(8) Uani . . 1.000 . -16
    C C3 0.38382(13) -0.5515(5) 0.2327(2) 0.0516(9) Uani . . 1.000 . -16
    C C4 0.42941(13) -0.6849(5) 0.1833(2) 0.0596(11) Uani . . 1.000 . -16
    C C5 0.43143(13) -0.6168(6) 0.0796(2) 0.0615(11) Uani . . 1.000 . -16
    C C6 0.38654(13) -0.4161(5) 0.0249(2) 0.0539(10) Uani . . 1.000 . -16
    C C7 0.29213(12) -0.0712(5) 0.00262(18) 0.0416(8) Uani . . 1.000 . -16
    C C8 0.19724(12) 0.2725(5) -0.00178(18) 0.0428(8) Uani . . 1.000 . -16
    C C9 0.18909(14) 0.3743(5) -0.1055(2) 0.0564(10) Uani . . 1.000 . -16
    C C10 0.13704(14) 0.5697(6) -0.1449(2) 0.0605(11) Uani . . 1.000 . -16
    C C11 0.09251(13) 0.6670(5) -0.0859(2) 0.0544(10) Uani . . 1.000 . -16
    C C12 0.10233(14) 0.5654(5) 0.0186(2) 0.0592(10) Uani . . 1.000 . -16
    C C13 0.15368(13) 0.3727(5) 0.06023(19) 0.0524(9) Uani . . 1.000 . -16
    C C14 0.03636(15) 0.8783(5) -0.1313(2) 0.0751(11) Uani . . 1.000 . -16
    H H1 0.29314 -0.29364 0.28396 0.0899 Uiso . . 1.000 . -16
    H H1A 0.25091 0.03812 0.11424 0.0525 Uiso . . 1.000 . -16
    H H3 0.38315 -0.59736 0.30329 0.0619 Uiso . . 1.000 . -16
    H H4 0.45896 -0.82174 0.22036 0.0714 Uiso . . 1.000 . -16
    H H5 0.46273 -0.70494 0.04648 0.0739 Uiso . . 1.000 . -16
    H H6 0.38794 -0.37165 -0.04556 0.0647 Uiso . . 1.000 . -16
    H H9 0.21810 0.31275 -0.14848 0.0677 Uiso . . 1.000 . -16
    H H10 0.13229 0.63728 -0.21461 0.0726 Uiso . . 1.000 . -16
    H H12 0.07355 0.62883 0.06158 0.0711 Uiso . . 1.000 . -16
    H H13 0.15915 0.30919 0.13074 0.0628 Uiso . . 1.000 . -16
    H H14A 0.03008 0.89281 -0.20839 0.1127 Uiso . . 1.000 . -16
    H H14B 0.05114 1.05104 -0.09782 0.1127 Uiso . . 1.000 . -16
    H H14C -0.00787 0.82537 -0.11655 0.1127 Uiso . . 1.000 . -16
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 . . 1.366(3) no
    O2 C7 . . 1.238(3) no
    O1 H1 . . 0.8200 no
    N1 C7 . . 1.339(3) no
    N1 C8 . . 1.419(3) no
    N1 H1A . . 0.8600 no
    C1 C7 . . 1.495(3) no
    C1 C6 . . 1.392(3) no
    C1 C2 . . 1.397(3) no
    C2 C3 . . 1.389(3) no
    C3 C4 . . 1.375(4) no
    C4 C5 . . 1.372(4) no
    C5 C6 . . 1.381(4) no
    C8 C13 . . 1.386(3) no
    C8 C9 . . 1.382(3) no
    C9 C10 . . 1.391(4) no
    C10 C11 . . 1.368(4) no
    C11 C12 . . 1.387(3) no
    C11 C14 . . 1.509(4) no
    C12 C13 . . 1.379(4) no
    C3 H3 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14A . . 0.9600 no
    C14 H14B . . 0.9600 no
    C14 H14C . . 0.9600 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 H1 . . . 109.00 no
    C7 N1 C8 . . . 128.90(19) no
    C8 N1 H1A . . . 116.00 no
    C7 N1 H1A . . . 116.00 no
    C2 C1 C6 . . . 117.5(2) no
    C2 C1 C7 . . . 125.8(2) no
    C6 C1 C7 . . . 116.7(2) no
    O1 C2 C3 . . . 120.6(2) no
    O1 C2 C1 . . . 119.2(2) no
    C1 C2 C3 . . . 120.3(2) no
    C2 C3 C4 . . . 120.6(2) no
    C3 C4 C5 . . . 120.2(2) no
    C4 C5 C6 . . . 119.3(2) no
    C1 C6 C5 . . . 122.1(2) no
    N1 C7 C1 . . . 118.03(19) no
    O2 C7 C1 . . . 120.5(2) no
    O2 C7 N1 . . . 121.5(2) no
    N1 C8 C9 . . . 124.5(2) no
    N1 C8 C13 . . . 117.0(2) no
    C9 C8 C13 . . . 118.5(2) no
    C8 C9 C10 . . . 119.3(2) no
    C9 C10 C11 . . . 123.1(2) no
    C10 C11 C14 . . . 121.7(2) no
    C10 C11 C12 . . . 116.7(2) no
    C12 C11 C14 . . . 121.6(2) no
    C11 C12 C13 . . . 121.6(2) no
    C8 C13 C12 . . . 120.8(2) no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C3 C4 H4 . . . 120.00 no
    C5 C4 H4 . . . 120.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 no
    C8 C9 H9 . . . 120.00 no
    C10 C9 H9 . . . 120.00 no
    C9 C10 H10 . . . 118.00 no
    C11 C10 H10 . . . 118.00 no
    C11 C12 H12 . . . 119.00 no
    C13 C12 H12 . . . 119.00 no
    C8 C13 H13 . . . 120.00 no
    C12 C13 H13 . . . 120.00 no
    C11 C14 H14A . . . 109.00 no
    C11 C14 H14B . . . 109.00 no
    C11 C14 H14C . . . 109.00 no
    H14A C14 H14B . . . 109.00 no
    H14A C14 H14C . . . 109.00 no
    H14B C14 H14C . . . 109.00 no
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 . . . . 2.0(4) no
    C8 N1 C7 C1 . . . . -178.1(2) no
    C7 N1 C8 C9 . . . . -6.3(4) no
    C7 N1 C8 C13 . . . . 174.3(2) no
    C6 C1 C2 O1 . . . . 179.2(2) no
    C6 C1 C2 C3 . . . . -0.5(4) no
    C7 C1 C2 O1 . . . . -2.3(4) no
    C7 C1 C2 C3 . . . . 177.9(2) no
    C2 C1 C6 C5 . . . . 0.3(4) no
    C7 C1 C6 C5 . . . . -178.3(2) no
    C2 C1 C7 O2 . . . . -176.0(2) no
    C2 C1 C7 N1 . . . . 4.1(4) no
    C6 C1 C7 O2 . . . . 2.5(3) no
    C6 C1 C7 N1 . . . . -177.5(2) no
    O1 C2 C3 C4 . . . . -179.8(2) no
    C1 C2 C3 C4 . . . . 0.0(4) no
    C2 C3 C4 C5 . . . . 0.8(4) no
    C3 C4 C5 C6 . . . . -1.0(4) no
    C4 C5 C6 C1 . . . . 0.4(4) no
    N1 C8 C9 C10 . . . . 179.6(2) no
    C13 C8 C9 C10 . . . . -1.0(4) no
    N1 C8 C13 C12 . . . . -179.2(2) no
    C9 C8 C13 C12 . . . . 1.4(4) no
    C8 C9 C10 C11 . . . . -0.4(4) no
    C9 C10 C11 C12 . . . . 1.4(4) no
    C9 C10 C11 C14 . . . . -179.7(2) no
    C10 C11 C12 C13 . . . . -1.0(4) no
    C14 C11 C12 C13 . . . . -179.9(2) no
    C11 C12 C13 C8 . . . . -0.4(4) no
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 4_545 0.82 1.78 2.596(2) 179 yes
    N1 H1A O1 . 0.86 1.92 2.647(2) 141 yes
    C3 H3 O2 4_545 0.93 2.51 3.179(3) 129 yes
    C9 H9 O2 . 0.93 2.25 2.840(3) 121 yes
