#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/54/2105484.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2105484
loop_
_publ_author_name
'Jones, Peter G.'
'Taouss, Christina'
'Teschmit, Nicole'
'Thomas, Lena'
_publ_section_title
;
 Methylthioureas and their morpholine and dioxane adducts;
 hydrogen-bonding patterns
;
_journal_coeditor_code           GP5065
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              405
_journal_page_last               413
_journal_paper_doi               10.1107/S2052519213013481
_journal_volume                  69
_journal_year                    2013
_chemical_formula_sum            'C5 H12 N2 S'
_chemical_formula_weight         132.23
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.641(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4621(2)
_cell_length_b                   12.0353(4)
_cell_length_c                   10.9309(4)
_cell_measurement_reflns_used    4399
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7833
_cell_measurement_theta_min      3.3787
_cell_volume                     715.10(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9123
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.79
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     40
_refine_ls_number_reflns         1072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0224
_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)+(0.0263P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                988
_reflns_number_total             1072
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL Judo in C2/c
CELL 0.71073   5.4621  12.0353  10.9309  90.0000  95.641  90.0000
ZERR    4.00   0.0002   0.0004   0.0004   0.0000   0.004   0.0000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N   S
UNIT  20   48   8   4
FMAP   2
PLAN   10
TEMP   -173
SIZE 0.2 0.2 0.2
ACTA 61
CONF
EQIV $1 x-0.5,y-0.5,z
HTAB C12 S1_$1
OMIT -2 0 4
OMIT -2 4 4
L.S.   4
WGHT    0.026300    0.363900
FVAR       7.82010
S1    4    0.500000    0.605826    0.250000    10.50000    0.02953    0.01594 =
         0.01703    0.00000    0.00277    0.00000
N1    3    0.382914    0.405189    0.331918    11.00000    0.01894    0.01893 =
         0.01455    0.00160    0.00598    0.00093
C2    1    0.500000    0.465194    0.250000    10.50000    0.01459    0.01799 =
         0.01118    0.00000    0.00040    0.00000
C11   1    0.197380    0.455169    0.401655    11.00000    0.01937    0.03129 =
         0.01712   -0.00116    0.00731    0.00177
AFIX 137
H11A  2    0.274454    0.479928    0.481767    11.00000   -1.50000
H11B  2    0.069630    0.400198    0.413793    11.00000   -1.50000
H11C  2    0.123230    0.519005    0.356322    11.00000   -1.50000
AFIX   0
C12   1    0.484122    0.300592    0.384050    11.00000    0.02635    0.01917 =
         0.01586    0.00315    0.00247   -0.00087
AFIX 137
H12A  2    0.641741    0.285160    0.351719    11.00000   -1.50000
H12B  2    0.368842    0.239904    0.361456    11.00000   -1.50000
H12C  2    0.509379    0.306856    0.473792    11.00000   -1.50000
HKLF 4
;
_cod_data_source_file            gp5065.cif
_cod_data_source_block           judo
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2105484
_cod_database_fobs_code          2105484
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.5000 0.60583(2) 0.2500 0.02080(10) Uani d S 1 2
N N1 0.38291(13) 0.40519(6) 0.33192(6) 0.01719(15) Uani d . 1 1
C C2 0.5000 0.46519(9) 0.2500 0.0146(2) Uani d S 1 2
C C11 0.19738(16) 0.45517(8) 0.40165(8) 0.02223(18) Uani d . 1 1
H H11A 0.2745 0.4799 0.4818 0.033 Uiso calc R 1 1
H H11B 0.0696 0.4002 0.4138 0.033 Uiso calc R 1 1
H H11C 0.1232 0.5190 0.3563 0.033 Uiso calc R 1 1
C C12 0.48412(16) 0.30059(7) 0.38405(7) 0.02043(17) Uani d . 1 1
H H12A 0.6417 0.2852 0.3517 0.031 Uiso calc R 1 1
H H12B 0.3688 0.2399 0.3615 0.031 Uiso calc R 1 1
H H12C 0.5094 0.3069 0.4738 0.031 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.02953(17) 0.01594(14) 0.01703(14) 0.000 0.00277(11) 0.000
N1 0.0189(3) 0.0189(3) 0.0145(3) 0.0009(2) 0.0060(2) 0.0016(2)
C2 0.0146(4) 0.0180(5) 0.0112(4) 0.000 0.0004(3) 0.000
C11 0.0194(4) 0.0313(4) 0.0171(4) 0.0018(3) 0.0073(3) -0.0012(3)
C12 0.0263(4) 0.0192(4) 0.0159(3) -0.0009(3) 0.0025(3) 0.0031(3)
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_site_symmetry_1
_geom_angle
C2 N1 C11 . 121.49(7)
C2 N1 C12 . 121.89(7)
C11 N1 C12 . 113.95(7)
N1 C2 N1 2_655 115.76(10)
N1 C2 S1 2_655 122.12(5)
N1 C11 H11A . 109.5
N1 C11 H11B . 109.5
H11A C11 H11B . 109.5
N1 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
N1 C12 H12A . 109.5
N1 C12 H12B . 109.5
H12A C12 H12B . 109.5
N1 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
N1 C2 S1 . 122.12(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C2 . 1.6925(11)
N1 C2 . 1.3583(9)
N1 C11 . 1.4566(10)
N1 C12 . 1.4674(10)
C2 N1 2_655 1.3583(9)
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12B S1 3_445 0.98 2.77 3.7246(9) 165.3
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_site_symmetry_4
_geom_torsion
C11 N1 C2 N1 2_655 -163.00(8)
C12 N1 C2 N1 2_655 36.64(6)
C11 N1 C2 S1 . 17.00(8)
C12 N1 C2 S1 . -143.36(6)
