#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:13:32 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208600.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_7208600
loop_
_publ_author_name
'Štrukil, Vjekoslav'
'Igrc, Marina D.'
'Fábián, László'
'Eckert-Maksić, Mirjana'
'Childs, Scott L.'
'Reid, David G.'
'Duer, Melinda J.'
'Halasz, Ivan'
'Mottillo, Cristina'
'Friščić, Tomislav'
_publ_section_title
;
 A model for a solvent-free synthetic organic research laboratory:
 click-mechanosynthesis and structural characterization of thioureas
 without bulk solvents
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2462
_journal_paper_doi               10.1039/c2gc35799b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C11 H14 N2 S2'
_chemical_formula_sum            'C11 H14 N2 S2'
_chemical_formula_weight         238.36
_chemical_name_common            N-phenyl-N'-(thiomorpholino)thiourea
_chemical_name_systematic
;
N-phenyl-N'-(thiomorpholino)thiourea
;
_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                 101.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5813(3)
_cell_length_b                   9.3856(3)
_cell_length_c                   10.8926(4)
_cell_measurement_reflns_used    14080
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     1161.41(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ 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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14713
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

multi-scan from symmetry-related measurements

Sortav (Blessing 1995)

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.305
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0472
_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)+(0.0375P)²+0.8600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2445
_reflns_number_total             3390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2gc35799b.txt
_cod_data_source_block           2k
_cod_original_cell_volume        1161.40(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7208600
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
S1 S 0.10691(6) 0.38058(8) 0.58833(7) 0.0389(2) Uani 1 1 d .
S2 S 0.48464(5) 0.18559(7) 0.92423(6) 0.02845(17) Uani 1 1 d .
N1 N 0.33462(17) 0.3786(2) 0.80123(19) 0.0260(4) Uani 1 1 d .
N2 N 0.53090(17) 0.4095(2) 0.79004(19) 0.0270(4) Uani 1 1 d .
H2 H 0.5052 0.4778 0.7362 0.032 Uiso 1 1 calc RD
C1 C 0.2351(2) 0.2896(3) 0.8178(3) 0.0346(6) Uani 1 1 d .
H1A H 0.1820 0.3451 0.8608 0.042 Uiso 1 1 calc R
H1B H 0.2643 0.2066 0.8710 0.042 Uiso 1 1 calc R
C2 C 0.1673(2) 0.2380(3) 0.6922(3) 0.0402(7) Uani 1 1 d .
H2B H 0.1022 0.1756 0.7065 0.048 Uiso 1 1 calc R
H2C H 0.2204 0.1800 0.6512 0.048 Uiso 1 1 calc R
C3 C 0.2403(2) 0.4843(3) 0.5988(2) 0.0311(6) Uani 1 1 d .
H3A H 0.2966 0.4321 0.5576 0.037 Uiso 1 1 calc R
H3B H 0.2216 0.5760 0.5545 0.037 Uiso 1 1 calc R
C4 C 0.2962(2) 0.5126(3) 0.7343(2) 0.0261(5) Uani 1 1 d .
H4A H 0.3649 0.5763 0.7378 0.031 Uiso 1 1 calc RD
H4B H 0.2388 0.5616 0.7762 0.031 Uiso 1 1 calc R
C5 C 0.4471(2) 0.3324(2) 0.8335(2) 0.0230(5) Uani 1 1 d .
C6 C 0.6537(2) 0.3916(2) 0.8220(2) 0.0244(5) Uani 1 1 d .
C7 C 0.7157(2) 0.3818(3) 0.7256(2) 0.0277(5) Uani 1 1 d .
H7 H 0.6750 0.3829 0.6410 0.033 Uiso 1 1 calc R
C8 C 0.8377(2) 0.3703(3) 0.7530(3) 0.0327(6) Uani 1 1 d .
H8 H 0.8805 0.3642 0.6871 0.039 Uiso 1 1 calc R
C9 C 0.8968(2) 0.3679(3) 0.8761(3) 0.0344(6) Uani 1 1 d .
H9 H 0.9800 0.3585 0.8949 0.041 Uiso 1 1 calc R
C10 C 0.8345(2) 0.3789(3) 0.9720(3) 0.0340(6) Uani 1 1 d .
H10 H 0.8754 0.3773 1.0566 0.041 Uiso 1 1 calc R
C11 C 0.7129(2) 0.3924(3) 0.9456(2) 0.0299(5) Uani 1 1 d .
H11 H 0.6706 0.4021 1.0116 0.036 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
S1 0.0283(3) 0.0402(4) 0.0441(4) 0.0018(3) -0.0029(3) -0.0006(3)
S2 0.0256(3) 0.0286(3) 0.0306(3) 0.0054(3) 0.0041(2) 0.0020(2)
N1 0.0218(10) 0.0253(10) 0.0310(11) 0.0060(9) 0.0056(8) 0.0002(8)
N2 0.0213(9) 0.0311(11) 0.0276(10) 0.0069(9) 0.0027(8) -0.0001(8)
C1 0.0213(12) 0.0365(15) 0.0471(16) 0.0147(13) 0.0092(11) 0.0002(10)
C2 0.0274(13) 0.0258(13) 0.065(2) 0.0036(13) 0.0019(13) -0.0021(11)
C3 0.0301(13) 0.0336(14) 0.0304(13) 0.0039(11) 0.0075(10) 0.0038(11)
C4 0.0248(12) 0.0224(11) 0.0315(13) 0.0013(10) 0.0062(10) 0.0013(9)
C5 0.0219(11) 0.0256(11) 0.0218(11) -0.0029(9) 0.0053(8) -0.0010(9)
C6 0.0211(11) 0.0226(11) 0.0290(12) 0.0000(10) 0.0034(9) -0.0014(9)
C7 0.0280(12) 0.0283(13) 0.0265(12) -0.0014(10) 0.0050(10) -0.0024(10)
C8 0.0279(13) 0.0331(14) 0.0399(15) -0.0036(12) 0.0139(11) -0.0004(10)
C9 0.0215(12) 0.0317(13) 0.0493(17) 0.0011(12) 0.0050(11) 0.0020(10)
C10 0.0272(13) 0.0370(15) 0.0344(14) 0.0014(12) -0.0026(10) -0.0028(11)
C11 0.0281(12) 0.0342(14) 0.0275(12) -0.0025(11) 0.0052(10) -0.0025(10)
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
C2 S1 C3 97.91(12)
C5 N1 C1 121.8(2)
C5 N1 C4 125.7(2)
C1 N1 C4 112.24(19)
C5 N2 C6 127.1(2)
C5 N2 H2 116.5
C6 N2 H2 116.5
N1 C1 C2 110.7(2)
N1 C1 H1A 109.5
C2 C1 H1A 109.5
N1 C1 H1B 109.5
C2 C1 H1B 109.5
H1A C1 H1B 108.1
C1 C2 S1 113.5(2)
C1 C2 H2B 108.9
S1 C2 H2B 108.9
C1 C2 H2C 108.9
S1 C2 H2C 108.9
H2B C2 H2C 107.7
C4 C3 S1 110.71(18)
C4 C3 H3A 109.5
S1 C3 H3A 109.5
C4 C3 H3B 109.5
S1 C3 H3B 109.5
H3A C3 H3B 108.1
N1 C4 C3 111.2(2)
N1 C4 H4A 109.4
C3 C4 H4A 109.4
N1 C4 H4B 109.4
C3 C4 H4B 109.4
H4A C4 H4B 108.0
N1 C5 N2 116.9(2)
N1 C5 S2 122.32(18)
N2 C5 S2 120.78(17)
C7 C6 C11 120.3(2)
C7 C6 N2 118.0(2)
C11 C6 N2 121.6(2)
C6 C7 C8 119.9(2)
C6 C7 H7 120.1
C8 C7 H7 120.1
C9 C8 C7 120.0(2)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 120.0(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C11 120.5(3)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C6 119.4(2)
C10 C11 H11 120.3
C6 C11 H11 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.804(3)
S1 C3 1.811(3)
S2 C5 1.702(2)
N1 C5 1.354(3)
N1 C1 1.463(3)
N1 C4 1.478(3)
N2 C5 1.367(3)
N2 C6 1.407(3)
N2 H2 0.8800
C1 C2 1.519(4)
C1 H1A 0.9900
C1 H1B 0.9900
C2 H2B 0.9900
C2 H2C 0.9900
C3 C4 1.515(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C6 C7 1.386(3)
C6 C11 1.388(3)
C7 C8 1.390(3)
C7 H7 0.9500
C8 C9 1.382(4)
C8 H8 0.9500
C9 C10 1.384(4)
C9 H9 0.9500
C10 C11 1.388(4)
C10 H10 0.9500
C11 H11 0.9500
