#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/53/7215338.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_7215338
loop_
_publ_author_name
'Guzei, Ilia A.'
'Gunn, Erica M.'
'Spencer, Lara C.'
'Schomaker, Jennifer M.'
'Rigoli, Jared W.'
_publ_section_title
;
 Polymorphism of
 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3444
_journal_paper_doi               10.1039/c1ce05098b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C16 H13 N3 O S'
_chemical_formula_sum            'C16 H13 N3 O S'
_chemical_formula_weight         295.35
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.0269(4)
_cell_length_b                   23.4679(6)
_cell_length_c                   6.9207(2)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3085
_cell_measurement_theta_min      3.7670
_cell_volume                     2765.41(12)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38391
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         71.85
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  0.8339
_exptl_absorpt_correction_T_min  0.4268
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0308
_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)+(0.0611P)²+0.9749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2571
_reflns_number_total             2682
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05098b.txt
_cod_data_source_block           schomaker03a
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               7215338
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
S1 S 0.239510(18) 0.420757(12) 0.19908(4) 0.01707(12) Uani 1 1 d .
O1 O 0.49575(5) 0.52343(4) 0.23689(13) 0.0210(2) Uani 1 1 d .
N1 N 0.38557(6) 0.46473(4) 0.21477(14) 0.0159(2) Uani 1 1 d .
N2 N 0.28766(6) 0.53073(4) 0.20329(13) 0.0151(2) Uani 1 1 d .
N3 N 0.35388(6) 0.71501(4) 0.23093(15) 0.0182(2) Uani 1 1 d .
C1 C 0.30525(7) 0.47667(5) 0.20454(15) 0.0146(2) Uani 1 1 d .
C2 C 0.35996(7) 0.55928(5) 0.21319(15) 0.0152(2) Uani 1 1 d .
C3 C 0.42533(7) 0.51684(5) 0.22331(16) 0.0165(3) Uani 1 1 d .
C4 C 0.37441(7) 0.61574(5) 0.21480(16) 0.0165(3) Uani 1 1 d .
H4 H 0.4283 0.6260 0.2230 0.020 Uiso 1 1 calc R
C5 C 0.31959(7) 0.66341(5) 0.20586(15) 0.0160(3) Uani 1 1 d .
C6 C 0.23911(7) 0.65726(5) 0.17088(18) 0.0181(3) Uani 1 1 d .
H6 H 0.2166 0.6206 0.1541 0.022 Uiso 1 1 calc R
C7 C 0.19299(7) 0.70579(5) 0.16117(18) 0.0198(3) Uani 1 1 d .
H7 H 0.1383 0.7028 0.1360 0.024 Uiso 1 1 calc R
C8 C 0.22740(8) 0.75868(6) 0.18850(17) 0.0204(3) Uani 1 1 d .
H8 H 0.1969 0.7925 0.1836 0.024 Uiso 1 1 calc R
C9 C 0.30759(8) 0.76092(5) 0.22326(17) 0.0203(3) Uani 1 1 d .
H9 H 0.3310 0.7972 0.2428 0.024 Uiso 1 1 calc R
C10 C 0.42188(7) 0.40967(5) 0.21308(17) 0.0158(3) Uani 1 1 d .
C11 C 0.42067(7) 0.37787(5) 0.04392(17) 0.0198(3) Uani 1 1 d .
H11 H 0.3950 0.3920 -0.0681 0.024 Uiso 1 1 calc R
C12 C 0.45758(7) 0.32502(5) 0.04094(19) 0.0226(3) Uani 1 1 d .
H12 H 0.4564 0.3026 -0.0732 0.027 Uiso 1 1 calc R
C13 C 0.49600(7) 0.30499(5) 0.20360(19) 0.0221(3) Uani 1 1 d .
H13 H 0.5219 0.2692 0.2000 0.026 Uiso 1 1 calc R
C14 C 0.49679(7) 0.33711(5) 0.37164(19) 0.0233(3) Uani 1 1 d .
H14 H 0.5231 0.3231 0.4830 0.028 Uiso 1 1 calc R
C15 C 0.45914(7) 0.38988(5) 0.37811(18) 0.0194(3) Uani 1 1 d .
H15 H 0.4590 0.4118 0.4934 0.023 Uiso 1 1 calc R
C16 C 0.14957(7) 0.46102(5) 0.20986(17) 0.0200(3) Uani 1 1 d .
H16A H 0.1496 0.4848 0.3262 0.030 Uiso 1 1 calc R
H16B H 0.1048 0.4348 0.2141 0.030 Uiso 1 1 calc R
H16C H 0.1454 0.4853 0.0952 0.030 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 S1 C16 98.73(6) yes
C1 N1 C3 107.48(9) ?
C1 N1 C10 127.07(10) ?
C3 N1 C10 125.44(10) ?
C1 N2 C2 105.23(10) ?
C9 N3 C5 117.47(11) ?
N2 C1 N1 114.86(10) ?
N2 C1 S1 126.23(10) ?
N1 C1 S1 118.91(9) ?
C4 C2 N2 129.05(11) ?
C4 C2 C3 121.24(11) ?
N2 C2 C3 109.71(10) ?
O1 C3 N1 126.39(11) ?
O1 C3 C2 130.90(11) ?
N1 C3 C2 102.71(9) ?
C2 C4 C5 129.57(11) ?
C2 C4 H4 115.2 ?
C5 C4 H4 115.2 ?
N3 C5 C6 122.42(11) ?
N3 C5 C4 113.84(11) ?
C6 C5 C4 123.72(11) ?
C7 C6 C5 118.61(12) ?
C7 C6 H6 120.7 ?
C5 C6 H6 120.7 ?
C8 C7 C6 119.37(11) ?
C8 C7 H7 120.3 ?
C6 C7 H7 120.3 ?
C7 C8 C9 118.27(11) ?
C7 C8 H8 120.9 ?
C9 C8 H8 120.9 ?
N3 C9 C8 123.85(11) ?
N3 C9 H9 118.1 ?
C8 C9 H9 118.1 ?
C11 C10 C15 121.42(11) ?
C11 C10 N1 119.03(10) ?
C15 C10 N1 119.53(10) ?
C10 C11 C12 119.02(11) ?
C10 C11 H11 120.5 ?
C12 C11 H11 120.5 ?
C13 C12 C11 120.29(11) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C12 C13 C14 120.16(11) ?
C12 C13 H13 119.9 ?
C14 C13 H13 119.9 ?
C13 C14 C15 120.34(11) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C10 C15 C14 118.76(11) ?
C10 C15 H15 120.6 ?
C14 C15 H15 120.6 ?
S1 C16 H16A 109.5 ?
S1 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
S1 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.7252(12) yes
S1 C16 1.8009(13) yes
O1 C3 1.2126(15) ?
N1 C1 1.3978(15) ?
N1 C3 1.3991(15) ?
N1 C10 1.4324(15) ?
N2 C1 1.3035(15) ?
N2 C2 1.4033(15) ?
N3 C9 1.3359(16) ?
N3 C5 1.3555(15) ?
C2 C4 1.3478(17) ?
C2 C3 1.4953(16) ?
C4 C5 1.4582(17) ?
C4 H4 0.9500 ?
C5 C6 1.3991(17) ?
C6 C7 1.3851(17) ?
C6 H6 0.9500 ?
C7 C8 1.3855(18) ?
C7 H7 0.9500 ?
C8 C9 1.3875(19) ?
C8 H8 0.9500 ?
C9 H9 0.9500 ?
C10 C11 1.3885(16) ?
C10 C15 1.3866(17) ?
C11 C12 1.3906(16) ?
C11 H11 0.9500 ?
C12 C13 1.3843(18) ?
C12 H12 0.9500 ?
C13 C14 1.3858(19) ?
C13 H13 0.9500 ?
C14 C15 1.3953(17) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
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
C2 N2 C1 N1 0.02(12)
C2 N2 C1 S1 178.83(8)
C3 N1 C1 N2 0.70(13)
C10 N1 C1 N2 -178.14(10)
C3 N1 C1 S1 -178.20(8)
C10 N1 C1 S1 2.95(15)
C16 S1 C1 N2 -3.99(11)
C16 S1 C1 N1 174.78(9)
C1 N2 C2 C4 179.49(11)
C1 N2 C2 C3 -0.70(11)
C1 N1 C3 O1 178.55(11)
C10 N1 C3 O1 -2.59(18)
C1 N1 C3 C2 -1.02(11)
C10 N1 C3 C2 177.85(10)
C4 C2 C3 O1 1.37(19)
N2 C2 C3 O1 -178.46(12)
C4 C2 C3 N1 -179.09(10)
N2 C2 C3 N1 1.08(11)
N2 C2 C4 C5 -0.33(19)
C3 C2 C4 C5 179.88(10)
C9 N3 C5 C6 0.72(17)
C9 N3 C5 C4 179.51(10)
C2 C4 C5 N3 173.49(11)
C2 C4 C5 C6 -7.74(19)
N3 C5 C6 C7 0.15(18)
C4 C5 C6 C7 -178.52(11)
C5 C6 C7 C8 -0.77(18)
C6 C7 C8 C9 0.52(18)
C5 N3 C9 C8 -1.01(18)
C7 C8 C9 N3 0.40(19)
C1 N1 C10 C11 69.70(15)
C3 N1 C10 C11 -108.94(13)
C1 N1 C10 C15 -111.94(13)
C3 N1 C10 C15 69.42(15)
C15 C10 C11 C12 0.13(17)
N1 C10 C11 C12 178.46(10)
C10 C11 C12 C13 -1.06(18)
C11 C12 C13 C14 1.09(18)
C12 C13 C14 C15 -0.20(18)
C11 C10 C15 C14 0.75(17)
N1 C10 C15 C14 -177.57(10)
C13 C14 C15 C10 -0.71(17)
