#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/53/7215337.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_7215337
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
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                90.00
_cell_angle_beta                 111.8165(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1716(2)
_cell_length_b                   12.1281(3)
_cell_length_c                   12.4038(3)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.35
_cell_measurement_theta_min      2.44
_cell_volume                     1420.57(6)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60° ω and 0.6° φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45510
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.35
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0395
_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)+(0.0584P)²+0.6808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                4961
_reflns_number_total             5485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05098b.txt
_cod_data_source_block           guzei08
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               7215337
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.55098(3) 0.57581(2) 0.13810(2) 0.02037(7) Uani 1 1 d .
O1 O 0.52548(9) 0.35655(8) 0.46838(8) 0.02756(18) Uani 1 1 d .
N1 N 0.50923(8) 0.46888(7) 0.31191(7) 0.01618(14) Uani 1 1 d .
N2 N 0.73641(8) 0.46311(7) 0.31997(7) 0.01493(14) Uani 1 1 d .
N3 N 1.05416(9) 0.26951(7) 0.60648(8) 0.01865(15) Uani 1 1 d .
C1 C 0.60812(9) 0.49810(8) 0.26349(8) 0.01470(15) Uani 1 1 d .
C2 C 0.72839(10) 0.40307(8) 0.41360(8) 0.01557(15) Uani 1 1 d .
C3 C 0.57953(10) 0.40310(8) 0.40839(9) 0.01849(17) Uani 1 1 d .
C4 C 0.83206(10) 0.34805(8) 0.49747(8) 0.01747(16) Uani 1 1 d .
H4 H 0.8044 0.3148 0.5551 0.021 Uiso 1 1 calc R
C5 C 0.97984(10) 0.33201(8) 0.51287(8) 0.01519(15) Uani 1 1 d .
C6 C 1.03991(10) 0.37376(8) 0.43642(8) 0.01677(16) Uani 1 1 d .
H6 H 0.9854 0.4178 0.3719 0.020 Uiso 1 1 calc R
C7 C 1.18033(10) 0.34985(9) 0.45637(9) 0.01889(17) Uani 1 1 d .
H7 H 1.2234 0.3769 0.4055 0.023 Uiso 1 1 calc R
C8 C 1.25700(10) 0.28581(9) 0.55183(9) 0.02004(18) Uani 1 1 d .
H8 H 1.3533 0.2680 0.5675 0.024 Uiso 1 1 calc R
C9 C 1.18970(10) 0.24845(9) 0.62386(9) 0.02027(18) Uani 1 1 d .
H9 H 1.2431 0.2053 0.6895 0.024 Uiso 1 1 calc R
C10 C 0.35888(9) 0.47401(8) 0.25488(8) 0.01632(16) Uani 1 1 d .
C11 C 0.28431(14) 0.56672(12) 0.26171(15) 0.0415(4) Uani 1 1 d .
H11 H 0.3321 0.6297 0.3035 0.050 Uiso 1 1 calc R
C12 C 0.13720(15) 0.56653(15) 0.20613(18) 0.0541(5) Uani 1 1 d .
H12 H 0.0843 0.6296 0.2110 0.065 Uiso 1 1 calc R
C13 C 0.06808(12) 0.47583(13) 0.14436(11) 0.0329(3) Uani 1 1 d .
H13 H -0.0320 0.4770 0.1058 0.039 Uiso 1 1 calc R
C14 C 0.14340(12) 0.38335(11) 0.13818(10) 0.0268(2) Uani 1 1 d .
H14 H 0.0955 0.3207 0.0957 0.032 Uiso 1 1 calc R
C15 C 0.28955(11) 0.38202(9) 0.19426(10) 0.02243(19) Uani 1 1 d .
H15 H 0.3419 0.3181 0.1910 0.027 Uiso 1 1 calc R
C16 C 0.71173(12) 0.57549(10) 0.10928(10) 0.0248(2) Uani 1 1 d .
H16B H 0.6968 0.6165 0.0376 0.037 Uiso 1 1 calc R
H16A H 0.7383 0.4993 0.1005 0.037 Uiso 1 1 calc R
H16C H 0.7876 0.6105 0.1741 0.037 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 0.0033 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'
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
_geom_angle_publ_flag
C1 S1 C16 98.71(5) yes
C3 N1 C1 107.04(8) ?
C3 N1 C10 124.29(8) ?
C1 N1 C10 125.89(8) ?
C1 N2 C2 105.10(8) ?
C9 N3 C5 117.21(9) ?
N2 C1 N1 115.11(8) ?
N2 C1 S1 126.74(7) ?
N1 C1 S1 118.15(7) ?
C4 C2 N2 128.83(9) ?
C4 C2 C3 121.53(8) ?
N2 C2 C3 109.61(8) ?
O1 C3 N1 125.92(9) ?
O1 C3 C2 131.00(9) ?
N1 C3 C2 103.05(8) ?
C2 C4 C5 129.75(9) ?
C2 C4 H4 115.1 ?
C5 C4 H4 115.1 ?
N3 C5 C6 122.48(8) ?
N3 C5 C4 113.98(8) ?
C6 C5 C4 123.51(8) ?
C7 C6 C5 118.91(9) ?
C7 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C6 C7 C8 118.96(9) ?
C6 C7 H7 120.5 ?
C8 C7 H7 120.5 ?
C9 C8 C7 118.46(9) ?
C9 C8 H8 120.8 ?
C7 C8 H8 120.8 ?
N3 C9 C8 123.98(9) ?
N3 C9 H9 118.0 ?
C8 C9 H9 118.0 ?
C11 C10 C15 120.73(10) ?
C11 C10 N1 121.22(9) ?
C15 C10 N1 118.04(9) ?
C10 C11 C12 118.84(12) ?
C10 C11 H11 120.6 ?
C12 C11 H11 120.6 ?
C13 C12 C11 120.60(12) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
C12 C13 C14 120.19(11) ?
C12 C13 H13 119.9 ?
C14 C13 H13 119.9 ?
C13 C14 C15 119.76(11) ?
C13 C14 H14 120.1 ?
C15 C14 H14 120.1 ?
C10 C15 C14 119.86(10) ?
C10 C15 H15 120.1 ?
C14 C15 H15 120.1 ?
S1 C16 H16B 109.5 ?
S1 C16 H16A 109.5 ?
H16B C16 H16A 109.5 ?
S1 C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
H16A 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 1.7242(9) yes
S1 C16 1.7989(11) yes
O1 C3 1.2159(12) ?
N1 C3 1.3943(12) ?
N1 C1 1.3954(12) ?
N1 C10 1.4279(12) ?
N2 C1 1.3017(11) ?
N2 C2 1.3986(12) ?
N3 C9 1.3385(13) ?
N3 C5 1.3572(12) ?
C2 C4 1.3506(13) ?
C2 C3 1.4914(13) ?
C4 C5 1.4561(13) ?
C4 H4 0.9500 ?
C5 C6 1.3999(13) ?
C6 C7 1.3866(13) ?
C6 H6 0.9500 ?
C7 C8 1.3881(14) ?
C7 H7 0.9500 ?
C8 C9 1.3882(15) ?
C8 H8 0.9500 ?
C9 H9 0.9500 ?
C10 C11 1.3766(15) ?
C10 C15 1.3832(14) ?
C11 C12 1.3955(18) ?
C11 H11 0.9500 ?
C12 C13 1.375(2) ?
C12 H12 0.9500 ?
C13 C14 1.3764(19) ?
C13 H13 0.9500 ?
C14 C15 1.3876(15) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 H16B 0.9800 ?
C16 H16A 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 1.24(11)
C2 N2 C1 S1 -179.14(7)
C3 N1 C1 N2 -2.88(12)
C10 N1 C1 N2 -164.53(9)
C3 N1 C1 S1 177.46(7)
C10 N1 C1 S1 15.81(13)
C16 S1 C1 N2 5.97(10)
C16 S1 C1 N1 -174.41(8)
C1 N2 C2 C4 178.76(10)
C1 N2 C2 C3 0.80(10)
C1 N1 C3 O1 -175.16(11)
C10 N1 C3 O1 -13.14(17)
C1 N1 C3 C2 2.97(10)
C10 N1 C3 C2 164.99(9)
C4 C2 C3 O1 -2.55(18)
N2 C2 C3 O1 175.58(12)
C4 C2 C3 N1 179.45(9)
N2 C2 C3 N1 -2.41(11)
N2 C2 C4 C5 -2.30(18)
C3 C2 C4 C5 175.45(10)
C9 N3 C5 C6 -0.04(15)
C9 N3 C5 C4 177.94(9)
C2 C4 C5 N3 -178.60(10)
C2 C4 C5 C6 -0.64(17)
N3 C5 C6 C7 0.48(15)
C4 C5 C6 C7 -177.31(9)
C5 C6 C7 C8 -0.35(15)
C6 C7 C8 C9 -0.17(15)
C5 N3 C9 C8 -0.53(16)
C7 C8 C9 N3 0.64(17)
C3 N1 C10 C11 109.96(15)
C1 N1 C10 C11 -91.41(15)
C3 N1 C10 C15 -68.73(13)
C1 N1 C10 C15 89.90(12)
C15 C10 C11 C12 -0.1(3)
N1 C10 C11 C12 -178.79(16)
C10 C11 C12 C13 -0.8(3)
C11 C12 C13 C14 1.0(3)
C12 C13 C14 C15 -0.2(2)
C11 C10 C15 C14 0.92(19)
N1 C10 C15 C14 179.62(10)
C13 C14 C15 C10 -0.76(19)
