#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2222330.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_2222330
loop_
_publ_author_name
'Shahwar, Durre'
'Tahir, M. Nawaz'
'Ahmad, Naeem'
'Yasmeen, Asma'
'Ullah, Saif'
_publ_section_title
;
Phenyl N-(2-methylphenyl)carbamate
;
_journal_coeditor_code HB5008
_journal_issue 7
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1629
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C14 H13 N O2'
_chemical_formula_moiety 'C14 H13 N O2'
_chemical_formula_sum 'C14 H13 N O2'
_chemical_formula_weight 227.25
_chemical_name_systematic
;
Phenyl N-(2-methylphenyl)carbamate
;
_space_group_IT_number 33
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_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 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 10.5736(9)
_cell_length_b 18.5414(14)
_cell_length_c 5.9681(4)
_cell_measurement_reflns_used 2241
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 28.56
_cell_measurement_theta_min 2.99
_cell_volume 1170.04(15)
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_data_reduction 'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (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 7.40
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD'
_diffrn_measurement_method \w
_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 0.0370
_diffrn_reflns_av_sigmaI/netI 0.0401
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_number 6929
_diffrn_reflns_theta_full 28.32
_diffrn_reflns_theta_max 28.32
_diffrn_reflns_theta_min 2.92
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.087
_exptl_absorpt_correction_T_max 0.989
_exptl_absorpt_correction_T_min 0.984
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.290
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 480
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.14
_refine_diff_density_max 0.125
_refine_diff_density_min -0.152
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 158
_refine_ls_number_reflns 1585
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.012
_refine_ls_R_factor_all 0.0799
_refine_ls_R_factor_gt 0.0390
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0728
_refine_ls_wR_factor_ref 0.0830
_reflns_number_gt 997
_reflns_number_total 1585
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file hb5008.cif
_[local]_cod_data_source_block I
_cod_database_code 2222330
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
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
O1 0.0456(10) 0.0665(11) 0.0662(11) 0.0037(8) -0.0135(9) -0.0153(10)
O2 0.0448(10) 0.0669(11) 0.0638(10) -0.0087(8) -0.0047(9) -0.0083(9)
N1 0.0419(11) 0.0632(13) 0.0591(12) -0.0031(11) -0.0084(12) -0.0090(11)
C1 0.0369(12) 0.0511(14) 0.0497(14) -0.0005(10) -0.0010(11) 0.0007(12)
C2 0.0439(13) 0.0417(13) 0.0620(15) -0.0029(11) -0.0062(11) 0.0052(12)
C3 0.0509(15) 0.0604(16) 0.0538(14) -0.0063(12) -0.0084(12) -0.0008(14)
C4 0.0625(15) 0.0521(15) 0.0683(18) -0.0070(12) 0.0069(14) -0.0096(14)
C5 0.0692(19) 0.0490(15) 0.079(2) 0.0116(13) 0.0064(15) 0.0095(15)
C6 0.0577(16) 0.0621(17) 0.0541(16) 0.0100(13) -0.0013(13) 0.0092(14)
C7 0.0484(14) 0.0513(14) 0.0418(11) -0.0019(12) -0.0080(12) 0.0035(11)
C8 0.0445(13) 0.0489(13) 0.0503(12) -0.0100(12) -0.0001(12) 0.0023(12)
C9 0.0479(14) 0.0562(14) 0.0484(14) -0.0180(11) 0.0020(11) 0.0013(13)
C10 0.0679(19) 0.0809(19) 0.0562(16) -0.0237(16) 0.0076(15) -0.0113(15)
C11 0.070(2) 0.072(2) 0.093(2) -0.0072(16) 0.0194(18) -0.0196(17)
C12 0.0536(17) 0.0682(19) 0.102(2) 0.0007(15) 0.0057(17) -0.0014(18)
C13 0.0509(16) 0.0598(17) 0.0689(16) -0.0023(12) -0.0067(13) 0.0042(14)
C14 0.0568(15) 0.084(2) 0.0601(14) -0.0133(14) -0.0147(13) 0.0003(15)
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_occupancy
O O1 0.27882(15) 0.33744(9) 0.6965(3) 0.0594(6) Uani 1.000
O O2 0.48038(14) 0.30458(9) 0.6133(3) 0.0585(6) Uani 1.000
N N1 0.30983(19) 0.24161(11) 0.4867(3) 0.0547(7) Uani 1.000
C C1 0.31727(19) 0.39161(13) 0.8463(4) 0.0459(8) Uani 1.000
C C2 0.3813(2) 0.37450(12) 1.0394(4) 0.0492(8) Uani 1.000
C C3 0.4089(2) 0.42831(13) 1.1897(4) 0.0550(9) Uani 1.000
C C4 0.3718(2) 0.49827(14) 1.1487(5) 0.0610(9) Uani 1.000
C C5 0.3068(2) 0.51391(15) 0.9561(4) 0.0657(10) Uani 1.000
C C6 0.2797(2) 0.46077(14) 0.8027(4) 0.0580(9) Uani 1.000
C C7 0.3691(2) 0.29463(12) 0.6005(4) 0.0472(8) Uani 1.000
C C8 0.3694(2) 0.19088(12) 0.3442(4) 0.0479(7) Uani 1.000
C C9 0.3097(2) 0.17293(13) 0.1431(4) 0.0508(8) Uani 1.000
C C10 0.3682(3) 0.12288(15) 0.0089(4) 0.0683(10) Uani 1.000
C C11 0.4814(3) 0.09134(15) 0.0662(6) 0.0783(12) Uani 1.000
C C12 0.5378(3) 0.10948(16) 0.2643(6) 0.0746(11) Uani 1.000
C C13 0.4824(2) 0.15870(14) 0.4054(5) 0.0599(9) Uani 1.000
C C14 0.1842(2) 0.20522(15) 0.0812(5) 0.0670(10) Uani 1.000
H H1 0.233(2) 0.2453(13) 0.486(5) 0.0657 Uiso 1.000
H H2 0.40570 0.32718 1.06787 0.0590 Uiso 1.000
H H3 0.45290 0.41743 1.32027 0.0660 Uiso 1.000
H H4 0.39062 0.53459 1.25089 0.0732 Uiso 1.000
H H5 0.28080 0.56101 0.92870 0.0787 Uiso 1.000
H H6 0.23641 0.47170 0.67139 0.0696 Uiso 1.000
H H10 0.33000 0.10987 -0.12545 0.0820 Uiso 1.000
H H11 0.51913 0.05797 -0.02901 0.0938 Uiso 1.000
H H12 0.61432 0.08830 0.30394 0.0895 Uiso 1.000
H H13 0.52051 0.17034 0.54111 0.0718 Uiso 1.000
H H14A 0.12302 0.19369 0.19447 0.1006 Uiso 1.000
H H14B 0.15695 0.18596 -0.06011 0.1006 Uiso 1.000
H H14C 0.19249 0.25665 0.06956 0.1006 Uiso 1.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C7 118.67(17) no
C7 N1 C8 125.43(19) no
C8 N1 H1 119.7(19) no
C7 N1 H1 113.9(18) no
O1 C1 C6 117.7(2) no
C2 C1 C6 121.3(2) no
O1 C1 C2 120.8(2) no
C1 C2 C3 119.0(2) no
C2 C3 C4 120.5(2) no
C3 C4 C5 119.4(2) no
C4 C5 C6 120.8(2) no
C1 C6 C5 119.0(2) no
O1 C7 N1 108.04(18) no
O2 C7 N1 127.1(2) no
O1 C7 O2 124.9(2) no
C9 C8 C13 120.9(2) no
N1 C8 C9 118.26(19) no
N1 C8 C13 120.8(2) no
C10 C9 C14 121.6(2) no
C8 C9 C10 117.3(2) no
C8 C9 C14 121.1(2) no
C9 C10 C11 122.3(3) no
C10 C11 C12 119.4(3) no
C11 C12 C13 120.5(3) no
C8 C13 C12 119.5(3) no
C1 C2 H2 121.00 no
C3 C2 H2 120.00 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 121.00 no
C5 C6 H6 120.00 no
C9 C10 H10 119.00 no
C11 C10 H10 119.00 no
C10 C11 H11 120.00 no
C12 C11 H11 120.00 no
C11 C12 H12 120.00 no
C13 C12 H12 120.00 no
C8 C13 H13 120.00 no
C12 C13 H13 120.00 no
C9 C14 H14A 109.00 no
C9 C14 H14B 109.00 no
C9 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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.405(3) no
O1 C7 1.367(3) no
O2 C7 1.194(3) no
N1 C7 1.349(3) no
N1 C8 1.416(3) no
N1 H1 0.82(2) no
C1 C6 1.367(3) no
C1 C2 1.374(3) no
C2 C3 1.373(3) no
C3 C4 1.377(4) no
C4 C5 1.370(4) no
C5 C6 1.375(4) no
C8 C13 1.385(3) no
C8 C9 1.396(3) no
C9 C10 1.373(4) no
C9 C14 1.502(3) no
C10 C11 1.375(4) no
C11 C12 1.366(5) no
C12 C13 1.373(4) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C10 H10 0.9300 no
C11 H11 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_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
C5 H5 CgB 3_555 0.93 2.95 3.714(3) 140 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
_geom_torsion_publ_flag
C7 O1 C1 C2 -60.4(3) no
C7 O1 C1 C6 124.9(2) no
C1 O1 C7 O2 -9.1(3) no
C1 O1 C7 N1 172.51(19) no
C8 N1 C7 O1 172.7(2) no
C8 N1 C7 O2 -5.7(4) no
C7 N1 C8 C9 -139.0(2) no
C7 N1 C8 C13 42.5(3) no
O1 C1 C2 C3 -175.14(19) no
C6 C1 C2 C3 -0.7(3) no
O1 C1 C6 C5 174.57(19) no
C2 C1 C6 C5 -0.1(3) no
C1 C2 C3 C4 0.7(3) no
C2 C3 C4 C5 0.0(3) no
C3 C4 C5 C6 -0.8(3) no
C4 C5 C6 C1 0.8(3) no
N1 C8 C9 C10 -179.1(2) no
N1 C8 C9 C14 -1.3(3) no
C13 C8 C9 C10 -0.6(4) no
C13 C8 C9 C14 177.2(2) no
N1 C8 C13 C12 179.8(2) no
C9 C8 C13 C12 1.3(4) no
C8 C9 C10 C11 -0.4(4) no
C14 C9 C10 C11 -178.2(3) no
C9 C10 C11 C12 0.7(5) no
C10 C11 C12 C13 0.0(5) no
C11 C12 C13 C8 -1.0(4) no