#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/48/2234855.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_2234855
loop_
_publ_author_name
'Aydın, Abdullah'
'Soyer, Zeynep'
'Akkurt, Mehmet'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H)-one
;
_journal_coeditor_code           XU5511
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1544
_journal_page_last               o1545
_journal_paper_doi               10.1107/S1600536812017709
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H11 Cl N2 O2'
_chemical_formula_moiety         'C14 H11 Cl N2 O2'
_chemical_formula_sum            'C14 H11 Cl N2 O2'
_chemical_formula_weight         274.70
_chemical_name_systematic
;
3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.129(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7379(5)
_cell_length_b                   12.4797(7)
_cell_length_c                   10.2392(7)
_cell_measurement_reflns_used    27572
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      2.09
_cell_volume                     1242.47(13)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_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 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20574
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XRED-32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0428
_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/[σ²(Fo²)+(0.0456P)²+0.2748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2544
_reflns_number_total             3051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5511.cif
_cod_data_source_block           I
_cod_original_cell_volume        1242.48(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234855
_cod_database_fobs_code          2234855
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.37199(5) 0.42730(6) -0.40607(5) 0.0887(2) Uani d . 1.000
O O1 0.61747(10) 0.34298(10) 0.11087(11) 0.0535(3) Uani d . 1.000
O O2 0.52561(13) 0.24080(12) 0.26644(11) 0.0679(4) Uani d . 1.000
N N1 0.41738(11) 0.26396(10) 0.06103(11) 0.0428(4) Uani d . 1.000
N N2 0.16989(12) 0.24829(12) 0.04683(12) 0.0508(4) Uani d . 1.000
C C1 0.45104(13) 0.32285(11) -0.04809(13) 0.0392(4) Uani d . 1.000
C C2 0.38425(14) 0.33757(13) -0.16827(14) 0.0454(4) Uani d . 1.000
C C3 0.45056(16) 0.40463(14) -0.25277(15) 0.0520(5) Uani d . 1.000
C C4 0.57449(16) 0.45354(13) -0.22095(18) 0.0553(5) Uani d . 1.000
C C5 0.64095(15) 0.43708(13) -0.09935(17) 0.0539(5) Uani d . 1.000
C C6 0.57568(14) 0.37153(12) -0.01549(15) 0.0447(4) Uani d . 1.000
C C7 0.51813(15) 0.27708(13) 0.15798(15) 0.0495(5) Uani d . 1.000
C C8 0.29647(15) 0.19414(13) 0.06944(15) 0.0479(5) Uani d . 1.000
C C9 0.11468(13) 0.31842(12) 0.13447(13) 0.0422(4) Uani d . 1.000
C C10 0.17189(15) 0.33453(13) 0.26004(14) 0.0475(4) Uani d . 1.000
C C11 0.10954(17) 0.40404(15) 0.34387(16) 0.0565(5) Uani d . 1.000
C C12 -0.00743(18) 0.45947(15) 0.30515(19) 0.0624(6) Uani d . 1.000
C C13 -0.06427(19) 0.44406(16) 0.1809(2) 0.0659(6) Uani d . 1.000
C C14 -0.00497(17) 0.37461(15) 0.09612(16) 0.0567(5) Uani d . 1.000
H H2 0.30060 0.30500 -0.19140 0.0550 Uiso c R 1.000
H H2A 0.12430 0.23690 -0.02610 0.0610 Uiso c R 1.000
H H4 0.61400 0.49800 -0.28140 0.0660 Uiso c R 1.000
H H5 0.72520 0.46880 -0.07610 0.0650 Uiso c R 1.000
H H8A 0.30210 0.13680 0.00590 0.0580 Uiso c R 1.000
H H8B 0.29860 0.16180 0.15570 0.0580 Uiso c R 1.000
H H10 0.25200 0.29870 0.28780 0.0570 Uiso c R 1.000
H H11 0.14770 0.41340 0.42830 0.0680 Uiso c R 1.000
H H12 -0.04750 0.50670 0.36210 0.0750 Uiso c R 1.000
H H13 -0.14370 0.48100 0.15370 0.0790 Uiso c R 1.000
H H14 -0.04490 0.36490 0.01240 0.0680 Uiso c R 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'
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
_geom_angle_publ_flag
C6 O1 C7 107.78(11) no
C1 N1 C7 109.19(11) no
C1 N1 C8 125.75(11) no
C7 N1 C8 124.99(12) no
C8 N2 C9 124.23(12) no
C9 N2 H2A 118.00 no
C8 N2 H2A 118.00 no
N1 C1 C6 106.29(12) no
N1 C1 C2 132.05(12) no
C2 C1 C6 121.65(13) no
C1 C2 C3 115.20(13) no
Cl1 C3 C4 118.73(13) no
Cl1 C3 C2 117.77(12) no
C2 C3 C4 123.49(15) no
C3 C4 C5 120.48(15) no
C4 C5 C6 116.25(14) no
C1 C6 C5 122.93(14) no
O1 C6 C5 128.24(13) no
O1 C6 C1 108.83(12) no
O1 C7 N1 107.90(12) no
O1 C7 O2 122.84(14) no
O2 C7 N1 129.27(15) no
N1 C8 N2 113.63(13) no
N2 C9 C10 122.83(13) no
C10 C9 C14 118.29(14) no
N2 C9 C14 118.87(13) no
C9 C10 C11 119.87(14) no
C10 C11 C12 121.47(16) no
C11 C12 C13 118.90(17) no
C12 C13 C14 120.73(17) no
C9 C14 C13 120.73(15) no
C1 C2 H2 122.00 no
C3 C2 H2 122.00 no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C4 C5 H5 122.00 no
C6 C5 H5 122.00 no
N1 C8 H8A 109.00 no
N1 C8 H8B 109.00 no
N2 C8 H8A 109.00 no
N2 C8 H8B 109.00 no
H8A C8 H8B 108.00 no
C9 C10 H10 120.00 no
C11 C10 H10 120.00 no
C10 C11 H11 119.00 no
C12 C11 H11 119.00 no
C11 C12 H12 121.00 no
C13 C12 H12 121.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
C9 C14 H14 120.00 no
C13 C14 H14 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.7315(16) no
O1 C6 1.3817(19) no
O1 C7 1.3769(19) no
O2 C7 1.198(2) no
N1 C1 1.3914(18) no
N1 C7 1.3669(19) no
N1 C8 1.4711(19) no
N2 C8 1.414(2) no
N2 C9 1.3831(19) no
N2 H2A 0.8600 no
C1 C2 1.3725(19) no
C1 C6 1.3818(19) no
C2 C3 1.388(2) no
C3 C4 1.376(2) no
C4 C5 1.387(2) no
C5 C6 1.368(2) no
C9 C14 1.398(2) no
C9 C10 1.388(2) no
C10 C11 1.384(2) no
C11 C12 1.373(2) no
C12 C13 1.373(3) no
C13 C14 1.376(3) no
C2 H2 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C8 H8A 0.9700 no
C8 H8B 0.9700 no
C10 H10 0.9300 no
C11 H11 0.9300 no
C12 H12 0.9300 no
C13 H13 0.9300 no
C14 H14 0.9300 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
N2 H2A O2 4_454 0.86 2.30 3.1296(17) 162 yes
C11 H11 Cl1 1_556 0.93 2.70 3.5295(17) 150 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 C6 C5 179.00(16) no
C6 O1 C7 O2 -178.94(16) no
C7 O1 C6 C1 -0.57(16) no
C6 O1 C7 N1 0.88(16) no
C7 N1 C1 C2 -178.96(16) no
C8 N1 C1 C2 3.9(2) no
C1 N1 C7 O1 -0.86(16) no
C8 N1 C7 O1 176.31(13) no
C1 N1 C7 O2 178.93(17) no
C8 N1 C7 O2 -3.9(3) no
C1 N1 C8 N2 -59.57(18) no
C7 N1 C8 N2 123.72(15) no
C8 N1 C1 C6 -176.64(13) no
C7 N1 C1 C6 0.51(16) no
C8 N2 C9 C10 -6.8(2) no
C9 N2 C8 N1 -72.99(18) no
C8 N2 C9 C14 174.17(15) no
C2 C1 C6 O1 179.57(13) no
N1 C1 C6 C5 -179.55(14) no
N1 C1 C2 C3 179.08(15) no
C6 C1 C2 C3 -0.3(2) no
N1 C1 C6 O1 0.04(16) no
C2 C1 C6 C5 0.0(2) no
C1 C2 C3 Cl1 -179.79(12) no
C1 C2 C3 C4 0.2(2) no
C2 C3 C4 C5 0.3(3) no
Cl1 C3 C4 C5 -179.75(13) no
C3 C4 C5 C6 -0.6(2) no
C4 C5 C6 C1 0.5(2) no
C4 C5 C6 O1 -179.03(15) no
N2 C9 C10 C11 -178.47(15) no
C14 C9 C10 C11 0.6(2) no
N2 C9 C14 C13 179.13(16) no
C10 C9 C14 C13 0.0(2) no
C9 C10 C11 C12 -1.1(3) no
C10 C11 C12 C13 0.9(3) no
C11 C12 C13 C14 -0.3(3) no
C12 C13 C14 C9 -0.2(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 651614
