#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:43:14 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179455 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/52/4335238.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4335238
loop_
_publ_author_name
'Yi Rong'
'Ahmed Al-Harbi'
'Benjamin Kriegel'
'Gerard Parkin'
_publ_section_title
;
 Structural Characterization of 2-Imidazolones: Comparison with their
 Heavier Chalcogen Counterparts
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7172
_journal_page_last               7182
_journal_paper_doi               10.1021/ic400788g
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C11 H14 N2 S'
_chemical_formula_weight         206.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.2250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7333(5)
_cell_length_b                   16.9079(10)
_cell_length_c                   8.4588(5)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.42
_cell_measurement_theta_min      2.41
_cell_volume                     1061.97(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18173
_diffrn_reflns_theta_full        32.66
_diffrn_reflns_theta_max         32.66
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.8785
_exptl_absorpt_correction_T_min  0.7957
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                3229
_reflns_number_total             3753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400788g_si_005.cif
_cod_data_source_block           tbss10
_cod_database_code               4335238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.43512(3) 0.569415(17) 0.25657(3) 0.02468(8) Uani 1 1 d .
N1 N 0.71958(12) 0.56127(5) 0.51943(11) 0.02047(17) Uani 1 1 d .
H1A H 0.6576 0.5363 0.5768 0.025 Uiso 1 1 calc R
N2 N 0.78938(11) 0.62202(5) 0.31493(10) 0.01805(16) Uani 1 1 d .
C11 C 0.65195(13) 0.58511(6) 0.36168(12) 0.01859(17) Uani 1 1 d .
C12 C 0.94667(13) 0.61989(5) 0.45019(12) 0.01801(17) Uani 1 1 d .
C13 C 0.89839(13) 0.58135(6) 0.57804(12) 0.01911(18) Uani 1 1 d .
C14 C 1.01615(15) 0.56932(6) 0.73323(14) 0.0246(2) Uani 1 1 d .
H14A H 0.9785 0.5434 0.8176 0.029 Uiso 1 1 calc R
C15 C 1.19066(15) 0.59666(7) 0.75997(14) 0.0281(2) Uani 1 1 d .
H15A H 1.2752 0.5900 0.8648 0.034 Uiso 1 1 calc R
C16 C 1.24253(14) 0.63382(7) 0.63361(15) 0.0275(2) Uani 1 1 d .
H16A H 1.3635 0.6514 0.6542 0.033 Uiso 1 1 calc R
C17 C 1.12411(14) 0.64615(6) 0.47857(13) 0.0233(2) Uani 1 1 d .
H17A H 1.1626 0.6717 0.3943 0.028 Uiso 1 1 calc R
C21 C 0.76488(14) 0.65787(6) 0.14662(12) 0.02052(18) Uani 1 1 d .
C22 C 0.70206(15) 0.59374(6) 0.01545(12) 0.0238(2) Uani 1 1 d .
H22A H 0.7922 0.5515 0.0340 0.036 Uiso 1 1 calc R
H22B H 0.6868 0.6168 -0.0939 0.036 Uiso 1 1 calc R
H22C H 0.5870 0.5719 0.0223 0.036 Uiso 1 1 calc R
C23 C 0.62914(17) 0.72566(7) 0.12381(14) 0.0295(2) Uani 1 1 d .
H23A H 0.6738 0.7654 0.2099 0.044 Uiso 1 1 calc R
H23B H 0.5133 0.7051 0.1314 0.044 Uiso 1 1 calc R
H23C H 0.6134 0.7499 0.0155 0.044 Uiso 1 1 calc R
C24 C 0.94162(16) 0.69102(8) 0.12826(14) 0.0304(2) Uani 1 1 d .
H24A H 0.9859 0.7323 0.2110 0.046 Uiso 1 1 calc R
H24B H 0.9217 0.7136 0.0179 0.046 Uiso 1 1 calc R
H24C H 1.0309 0.6485 0.1441 0.046 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.01869(13) 0.03312(15) 0.02161(13) 0.00259(9) 0.00457(9) -0.00403(9)
N1 0.0196(4) 0.0236(4) 0.0186(4) 0.0022(3) 0.0060(3) -0.0034(3)
N2 0.0193(4) 0.0178(4) 0.0177(3) 0.0008(3) 0.0063(3) -0.0016(3)
C11 0.0201(4) 0.0178(4) 0.0186(4) -0.0002(3) 0.0066(3) -0.0009(3)
C12 0.0191(4) 0.0158(4) 0.0200(4) -0.0009(3) 0.0067(3) 0.0004(3)
C13 0.0194(4) 0.0179(4) 0.0202(4) -0.0003(3) 0.0060(3) -0.0003(3)
C14 0.0238(5) 0.0273(5) 0.0213(5) 0.0031(4) 0.0042(4) 0.0007(4)
C15 0.0222(5) 0.0315(5) 0.0270(5) 0.0019(4) 0.0010(4) 0.0006(4)
C16 0.0183(4) 0.0295(5) 0.0334(5) 0.0011(4) 0.0048(4) -0.0013(4)
C17 0.0202(4) 0.0234(5) 0.0277(5) 0.0006(4) 0.0090(4) -0.0012(3)
C21 0.0259(5) 0.0183(4) 0.0185(4) 0.0029(3) 0.0080(3) -0.0004(3)
C22 0.0301(5) 0.0241(5) 0.0184(4) -0.0010(3) 0.0087(4) -0.0013(4)
C23 0.0395(6) 0.0217(5) 0.0275(5) 0.0045(4) 0.0098(4) 0.0075(4)
C24 0.0333(6) 0.0328(6) 0.0268(5) 0.0060(4) 0.0114(4) -0.0095(4)
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'
S S 0.1246 0.1234 '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
C11 N1 C13 110.80(8)
C11 N2 C12 108.21(8)
C11 N2 C21 123.17(8)
C12 N2 C21 128.62(8)
N1 C11 N2 107.50(8)
N1 C11 S 121.84(7)
N2 C11 S 130.66(7)
C17 C12 C13 118.43(9)
C17 C12 N2 135.23(9)
C13 C12 N2 106.34(8)
N1 C13 C14 129.27(10)
N1 C13 C12 107.15(9)
C14 C13 C12 123.56(10)
C15 C14 C13 117.25(10)
C14 C15 C16 120.15(10)
C17 C16 C15 122.48(10)
C16 C17 C12 118.10(10)
N2 C21 C24 111.33(8)
N2 C21 C23 108.71(8)
C24 C21 C23 108.35(9)
N2 C21 C22 109.27(8)
C24 C21 C22 107.37(9)
C23 C21 C22 111.83(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C11 1.6851(10)
N1 C11 1.3516(12)
N1 C13 1.3748(13)
N2 C11 1.3821(12)
N2 C12 1.4185(12)
N2 C21 1.5098(12)
C12 C17 1.3977(14)
C12 C13 1.3997(13)
C13 C14 1.3878(14)
C14 C15 1.3840(16)
C15 C16 1.3920(17)
C16 C17 1.3896(15)
C21 C24 1.5248(15)
C21 C23 1.5295(15)
C21 C22 1.5303(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A S 0.88 2.50 3.3422(9) 160.0 3_666
