#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/48/2214868.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_2214868
loop_
_publ_author_name
'Hong-Gang An'
_publ_section_title
;
 (E)-N-(1,3-Oxazolidin-2-ylidene)benzamide
;
_journal_coeditor_code           TK2168
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3357
_journal_page_last               o3357
_journal_paper_doi               10.1107/S1600536807030772
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H10 N2 O2'
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20
_chemical_melting_point          411.5(5)
_chemical_name_systematic
;
(E)-N-(1,3-Oxazolidin-2-ylidene)benzamide
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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            8
_cell_length_a                   11.4194(18)
_cell_length_b                   20.590(3)
_cell_length_c                   8.0325(13)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3
_cell_measurement_theta_min      3.3
_cell_volume                     1888.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9475
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       0.0047(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.045
_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)+(0.064P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                1091
_reflns_number_total             1850
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2168.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '411-412' was changed to '411.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '411-412' was changed to '411.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1888.7(5)
_cod_database_code               2214868
_cod_database_fobs_code          2214868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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
C C1 0.34177(19) 0.35640(11) 0.2998(3) 0.0796(7) Uani d . 1
H H1 0.3107 0.3467 0.1958 0.096 Uiso calc R 1
C C2 0.33903(19) 0.41901(11) 0.3592(3) 0.0792(7) Uani d . 1
H H2 0.3060 0.4518 0.2948 0.095 Uiso calc R 1
C C3 0.38492(17) 0.43353(9) 0.5133(2) 0.0652(5) Uani d . 1
H H3 0.3824 0.4760 0.5523 0.078 Uiso calc R 1
C C4 0.43460(15) 0.38564(8) 0.6105(2) 0.0518(5) Uani d . 1
C C5 0.43765(17) 0.32282(9) 0.5492(2) 0.0606(5) Uani d . 1
H H5 0.4716 0.2900 0.6123 0.073 Uiso calc R 1
C C6 0.3907(2) 0.30858(10) 0.3953(3) 0.0734(6) Uani d . 1
H H6 0.3923 0.2661 0.3561 0.088 Uiso calc R 1
C C7 0.48292(16) 0.40198(8) 0.7777(2) 0.0539(5) Uani d . 1
C C8 0.58435(15) 0.35996(8) 1.0000(2) 0.0514(5) Uani d . 1
C C9 0.6620(2) 0.39852(9) 1.2444(2) 0.0701(6) Uani d . 1
H H9A 0.6106 0.4059 1.3387 0.084 Uiso calc R 1
H H9B 0.7325 0.4243 1.2574 0.084 Uiso calc R 1
C C10 0.69031(19) 0.32699(9) 1.2239(2) 0.0709(6) Uani d . 1
H H10A 0.7742 0.3204 1.2149 0.085 Uiso calc R 1
H H10B 0.6611 0.3021 1.3177 0.085 Uiso calc R 1
N N1 0.60390(14) 0.41239(7) 1.08905(18) 0.0630(5) Uani d . 1
H H11 0.5746 0.4494 1.0618 0.076 Uiso d R 1
N N2 0.53248(13) 0.35040(7) 0.85798(18) 0.0557(4) Uani d . 1
O O1 0.47644(13) 0.45792(6) 0.83169(16) 0.0782(5) Uani d . 1
O O2 0.63240(12) 0.30804(6) 1.07298(15) 0.0702(4) Uani d . 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
C1 0.0837(16) 0.0822(17) 0.0728(14) 0.0054(13) -0.0193(12) -0.0120(12)
C2 0.0868(16) 0.0684(15) 0.0823(15) 0.0118(12) -0.0207(13) 0.0051(12)
C3 0.0741(13) 0.0489(11) 0.0725(12) 0.0070(10) -0.0089(11) -0.0020(10)
C4 0.0559(11) 0.0425(10) 0.0568(10) 0.0018(8) 0.0024(9) -0.0010(8)
C5 0.0740(13) 0.0465(11) 0.0613(11) 0.0053(9) -0.0016(10) -0.0052(9)
C6 0.0869(15) 0.0582(13) 0.0749(13) 0.0031(11) -0.0054(12) -0.0148(10)
C7 0.0604(12) 0.0413(10) 0.0601(11) 0.0024(8) 0.0036(9) -0.0008(8)
C8 0.0566(11) 0.0381(10) 0.0595(11) 0.0041(8) 0.0055(9) -0.0014(8)
C9 0.0838(15) 0.0544(12) 0.0723(13) 0.0090(10) -0.0162(11) -0.0075(10)
C10 0.0814(14) 0.0557(12) 0.0756(13) 0.0105(10) -0.0195(11) -0.0054(10)
N1 0.0832(12) 0.0403(9) 0.0655(9) 0.0110(8) -0.0120(9) -0.0057(7)
N2 0.0694(10) 0.0404(9) 0.0572(9) 0.0036(7) -0.0051(8) -0.0042(7)
O1 0.1163(12) 0.0400(8) 0.0782(9) 0.0130(8) -0.0197(8) -0.0105(6)
O2 0.0925(10) 0.0420(7) 0.0760(9) 0.0129(6) -0.0233(8) -0.0034(6)
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
C6 C1 C2 119.4(2)
C6 C1 H1 120.3
C2 C1 H1 120.3
C1 C2 C3 120.44(19)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 120.66(18)
C2 C3 H3 119.7
C4 C3 H3 119.7
C3 C4 C5 118.47(17)
C3 C4 C7 120.05(16)
C5 C4 C7 121.48(16)
C6 C5 C4 120.52(17)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C6 C5 120.6(2)
C1 C6 H6 119.7
C5 C6 H6 119.7
O1 C7 N2 125.85(17)
O1 C7 C4 120.36(16)
N2 C7 C4 113.79(15)
N2 C8 N1 132.76(16)
N2 C8 O2 116.77(15)
N1 C8 O2 110.42(16)
N1 C9 C10 101.33(15)
N1 C9 H9A 111.5
C10 C9 H9A 111.5
N1 C9 H9B 111.5
C10 C9 H9B 111.5
H9A C9 H9B 109.3
O2 C10 C9 104.92(14)
O2 C10 H10A 110.8
C9 C10 H10A 110.8
O2 C10 H10B 110.8
C9 C10 H10B 110.8
H10A C10 H10B 108.8
C8 N1 C9 112.72(15)
C8 N1 H11 121.5
C9 N1 H11 125.1
C8 N2 C7 119.04(14)
C8 O2 C10 109.99(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.367(3)
C1 C2 1.375(3)
C1 H1 0.9300
C2 C3 1.377(3)
C2 H2 0.9300
C3 C4 1.380(2)
C3 H3 0.9300
C4 C5 1.384(2)
C4 C7 1.491(2)
C5 C6 1.379(2)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.2328(19)
C7 N2 1.365(2)
C8 N2 1.301(2)
C8 N1 1.314(2)
C8 O2 1.3368(19)
C9 N1 1.442(2)
C9 C10 1.517(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O2 1.435(2)
C10 H10A 0.9700
C10 H10B 0.9700
N1 H11 0.8599
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 H11 O1 . 0.86 2.17 2.696(2) 119
N1 H11 O1 5_667 0.86 2.17 2.8944(19) 142
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123762
