#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180097 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054398.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_7054398
loop_
_publ_author_name
'Palmer, Joshua H.'
'Parkin, Gerard'
_publ_section_title
;
 Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones
 and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse
 Substituents: A Manifold of Hydrogen Bonding Networks.
;
_journal_issue                   9
_journal_name_full
'New journal of chemistry = Nouveau journal de chimie'
_journal_page_first              4071
_journal_page_last               4082
_journal_paper_doi               10.1039/C4NJ00521J
_journal_volume                  38
_journal_year                    2014
_chemical_formula_sum            'C12 H14 N2 O3 S'
_chemical_formula_weight         266.31
_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                 93.0750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2383(6)
_cell_length_b                   7.9459(7)
_cell_length_c                   22.324(2)
_cell_measurement_reflns_used    5910
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.72
_cell_volume                     1282.11(19)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7575
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0426
_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)+(0.0417P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                2649
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7054266
_cod_data_source_file            c4nj00521j2.cif
_cod_data_source_block           hmimome3ph
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 

 Adding full bibliography for 7054264--7054403.cif.
;
_cod_original_cell_volume        1282.12(19)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7054398
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 0.22236(6) 0.36594(6) 0.45132(2) 0.02677(12) Uani 1 1 d .
N1 N -0.15151(18) 0.33228(18) 0.45326(6) 0.0240(3) Uani 1 1 d .
H1 H -0.162(3) 0.411(3) 0.4828(9) 0.039(6) Uiso 1 1 d .
N2 N -0.03361(17) 0.17068(16) 0.38823(6) 0.0198(3) Uani 1 1 d .
O1 O 0.49482(15) -0.18911(15) 0.35457(5) 0.0254(3) Uani 1 1 d .
O2 O 0.41567(16) -0.17837(14) 0.23741(5) 0.0244(3) Uani 1 1 d .
O3 O 0.15106(16) 0.02225(14) 0.18957(5) 0.0248(3) Uani 1 1 d .
C1 C 0.0914(2) 0.08927(19) 0.34967(7) 0.0195(3) Uani 1 1 d .
C2 C 0.2354(2) -0.00648(19) 0.37473(7) 0.0201(3) Uani 1 1 d .
H2A H 0.2565 -0.0140 0.4170 0.024 Uiso 1 1 calc R
C3 C 0.3483(2) -0.09126(19) 0.33631(7) 0.0199(3) Uani 1 1 d .
C4 C 0.3148(2) -0.08098(19) 0.27426(7) 0.0201(3) Uani 1 1 d .
C5 C 0.1708(2) 0.01921(19) 0.25043(7) 0.0199(3) Uani 1 1 d .
C6 C 0.0568(2) 0.10535(19) 0.28843(7) 0.0207(3) Uani 1 1 d .
H6A H -0.0422 0.1734 0.2726 0.025 Uiso 1 1 calc R
C7 C 0.5180(3) -0.2288(2) 0.41683(8) 0.0329(4) Uani 1 1 d .
H7A H 0.6208 -0.3082 0.4232 0.049 Uiso 1 1 calc R
H7B H 0.4042 -0.2799 0.4303 0.049 Uiso 1 1 calc R
H7C H 0.5450 -0.1257 0.4397 0.049 Uiso 1 1 calc R
C8 C 0.5650(2) -0.0924(2) 0.21140(9) 0.0334(4) Uani 1 1 d .
H8A H 0.6193 -0.1653 0.1816 0.050 Uiso 1 1 calc R
H8B H 0.6594 -0.0638 0.2429 0.050 Uiso 1 1 calc R
H8C H 0.5187 0.0109 0.1919 0.050 Uiso 1 1 calc R
C9 C 0.0244(3) 0.1417(2) 0.16352(8) 0.0293(4) Uani 1 1 d .
H9A H 0.0317 0.1406 0.1198 0.044 Uiso 1 1 calc R
H9B H 0.0558 0.2542 0.1789 0.044 Uiso 1 1 calc R
H9C H -0.1015 0.1126 0.1739 0.044 Uiso 1 1 calc R
C10 C 0.0110(2) 0.2879(2) 0.43107(7) 0.0207(3) Uani 1 1 d .
C11 C -0.2966(2) 0.2467(2) 0.42464(8) 0.0280(4) Uani 1 1 d .
H11A H -0.4240 0.2570 0.4323 0.034 Uiso 1 1 calc R
C12 C -0.2238(2) 0.1464(2) 0.38399(8) 0.0263(4) Uani 1 1 d .
H12A H -0.2899 0.0723 0.3572 0.032 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 0.01696(19) 0.0327(2) 0.0306(2) -0.01209(18) 0.00053(15) 0.00078(17)
N1 0.0180(6) 0.0285(8) 0.0257(7) -0.0071(6) 0.0039(5) 0.0014(6)
N2 0.0150(6) 0.0222(7) 0.0224(7) -0.0036(5) 0.0030(5) -0.0009(5)
O1 0.0233(6) 0.0275(6) 0.0249(6) 0.0006(5) -0.0020(5) 0.0069(5)
O2 0.0271(6) 0.0210(6) 0.0259(6) -0.0028(5) 0.0079(5) 0.0041(5)
O3 0.0290(6) 0.0259(6) 0.0195(6) -0.0015(5) 0.0010(5) 0.0083(5)
C1 0.0185(7) 0.0185(7) 0.0220(8) -0.0050(6) 0.0046(6) -0.0026(6)
C2 0.0198(7) 0.0213(8) 0.0190(7) -0.0015(6) 0.0004(6) -0.0013(6)
C3 0.0173(7) 0.0167(7) 0.0255(8) 0.0000(6) -0.0006(6) -0.0008(6)
C4 0.0196(7) 0.0175(7) 0.0235(8) -0.0028(6) 0.0034(6) 0.0003(6)
C5 0.0228(8) 0.0176(7) 0.0193(8) -0.0021(6) 0.0016(6) -0.0017(6)
C6 0.0192(7) 0.0186(7) 0.0242(8) -0.0019(6) 0.0009(6) 0.0008(6)
C7 0.0346(10) 0.0353(10) 0.0283(9) 0.0065(8) -0.0023(8) 0.0045(8)
C8 0.0282(9) 0.0347(10) 0.0384(11) 0.0005(8) 0.0135(8) 0.0039(8)
C9 0.0355(10) 0.0288(9) 0.0230(8) 0.0008(7) -0.0029(7) 0.0087(8)
C10 0.0216(8) 0.0216(8) 0.0189(8) -0.0017(6) 0.0021(6) 0.0017(6)
C11 0.0165(7) 0.0341(9) 0.0336(10) -0.0056(8) 0.0041(7) -0.0029(7)
C12 0.0172(7) 0.0306(9) 0.0312(9) -0.0049(7) 0.0029(6) -0.0050(7)
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
C10 N1 C11 111.04(14)
C10 N2 C12 109.87(13)
C10 N2 C1 126.59(13)
C12 N2 C1 123.43(13)
C3 O1 C7 117.90(13)
C4 O2 C8 114.46(12)
C5 O3 C9 116.87(12)
C6 C1 C2 122.88(14)
C6 C1 N2 117.70(14)
C2 C1 N2 119.37(14)
C1 C2 C3 118.16(15)
O1 C3 C2 124.54(15)
O1 C3 C4 114.99(14)
C2 C3 C4 120.46(14)
O2 C4 C5 120.36(14)
O2 C4 C3 119.55(14)
C5 C4 C3 119.94(14)
O3 C5 C4 115.37(14)
O3 C5 C6 124.44(14)
C4 C5 C6 120.18(15)
C1 C6 C5 118.33(14)
N1 C10 N2 104.96(13)
N1 C10 S 126.98(12)
N2 C10 S 128.04(12)
C12 C11 N1 106.86(14)
C11 C12 N2 107.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C10 1.6895(16)
N1 C10 1.348(2)
N1 C11 1.379(2)
N2 C10 1.362(2)
N2 C12 1.388(2)
N2 C1 1.4357(19)
O1 C3 1.3595(18)
O1 C7 1.426(2)
O2 C4 1.3688(18)
O2 C8 1.428(2)
O3 C5 1.3586(18)
O3 C9 1.4221(19)
C1 C6 1.382(2)
C1 C2 1.384(2)
C2 C3 1.390(2)
C3 C4 1.396(2)
C4 C5 1.394(2)
C5 C6 1.395(2)
C11 C12 1.337(2)
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 H1 S 0.91(2) 2.36(2) 3.2662(15) 171.2(17) 3_566
