#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220767.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_2220767
loop_
_publ_author_name
'Hanusek, Jiří'
'Sedlák, Miloš'
'Drabina, Pavel'
'Ružička, Aleš'
_publ_section_title
;
 (3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]thiouronium
 bromide
;
_journal_coeditor_code           FB2122
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o411
_journal_page_last               o412
_journal_paper_doi               10.1107/S1600536809001603
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H13 Cl N3 O S +, Br -'
_chemical_formula_moiety         'C11 H13 Cl N3 O S +, Br -'
_chemical_formula_sum            'C11 H13 Br Cl N3 O S'
_chemical_formula_weight         350.66
_chemical_name_systematic
;
(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]thiouronium
bromide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.329(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7379(9)
_cell_length_b                   6.4250(5)
_cell_length_c                   15.0531(7)
_cell_measurement_reflns_used    15779
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1352.22(16)
_computing_cell_refinement
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15769
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.383
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.473
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0504
_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)+(0.0236P)²+1.6718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                2214
_reflns_number_total             3095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2122.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220767
_cod_database_fobs_code          2220767
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_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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.48049(3) 0.45589(6) 0.65892(3) 0.04086(16) Uani d . 1 . .
S S1 0.34553(7) 0.14593(15) 0.41198(8) 0.0339(2) Uani d . 1 . .
Cl Cl1 -0.19436(7) 0.30572(19) -0.02926(9) 0.0532(3) Uani d . 1 . .
O O1 0.21265(19) -0.2562(4) 0.2711(2) 0.0450(7) Uani d . 1 . .
C C5 0.0464(3) 0.0076(6) 0.1482(3) 0.0295(8) Uani d . 1 . .
C C6 -0.0184(3) 0.1577(6) 0.0890(3) 0.0330(9) Uani d . 1 . .
H H6 0.0040 0.2871 0.0774 0.040 Uiso calc R 1 . .
C C4 0.3119(3) 0.0455(6) 0.2870(3) 0.0346(9) Uani d . 1 . .
H H4 0.3640 -0.0404 0.2852 0.042 Uiso calc R 1 . .
C C11 0.3880(2) -0.0716(6) 0.4901(3) 0.0291(8) Uani d . 1 . .
C C2 0.1792(3) 0.2598(6) 0.1780(3) 0.0372(10) Uani d . 1 . .
H H2A 0.1660 0.3657 0.2179 0.045 Uiso calc R 1 . .
H H2B 0.1480 0.3027 0.1069 0.045 Uiso calc R 1 . .
C C1 0.2191(3) -0.0747(6) 0.2493(3) 0.0329(9) Uani d . 1 . .
C C10 0.0120(3) -0.1790(7) 0.1662(3) 0.0398(10) Uani d . 1 . .
H H10 0.0552 -0.2828 0.2072 0.048 Uiso calc R 1 . .
C C8 -0.1500(3) -0.0645(7) 0.0639(3) 0.0422(10) Uani d . 1 . .
H H8 -0.2169 -0.0891 0.0349 0.051 Uiso calc R 1 . .
C C7 -0.1148(3) 0.1186(7) 0.0473(3) 0.0375(9) Uani d . 1 . .
C C9 -0.0854(3) -0.2119(7) 0.1239(3) 0.0459(11) Uani d . 1 . .
H H9 -0.1085 -0.3394 0.1364 0.055 Uiso calc R 1 . .
C C3 0.2862(3) 0.2309(7) 0.2163(3) 0.0410(10) Uani d . 1 . .
H H3A 0.3216 0.3568 0.2522 0.049 Uiso calc R 1 . .
H H3B 0.3012 0.2018 0.1605 0.049 Uiso calc R 1 . .
N N2A 0.4287(2) -0.0308(5) 0.5862(2) 0.0359(8) Uani d . 1 . .
H H2AA 0.4517 -0.1329 0.6299 0.043 Uiso calc R 1 . .
H H2AB 0.4331 0.0986 0.6070 0.043 Uiso calc R 1 . .
N N1 0.1455(2) 0.0527(5) 0.1902(2) 0.0301(7) Uani d . 1 . .
N N3A 0.3800(2) -0.2598(5) 0.4563(3) 0.0387(8) Uani d . 1 . .
H H3AA 0.4023 -0.3650 0.4982 0.046 Uiso calc R 1 . .
H H3AB 0.3523 -0.2825 0.3914 0.046 Uiso calc R 1 . .
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'
Br Br -0.2901 2.4595 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.015
0 0 1 0.015
0 -1 0 0.143
0 1 0 0.088
-1 0 0 0.045
1 0 0 0.045
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C4 . . 104.56(18) ?
C6 C5 C10 . . 119.1(3) ?
C6 C5 N1 . . 118.5(3) ?
C10 C5 N1 . . 122.4(3) ?
C7 C6 C5 . . 119.9(4) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C1 C4 C3 . . 103.7(3) ?
C1 C4 S1 . . 109.9(3) ?
C3 C4 S1 . . 107.6(3) ?
C1 C4 H4 . . 111.8 ?
C3 C4 H4 . . 111.8 ?
S1 C4 H4 . . 111.8 ?
N3A C11 N2A . . 122.0(4) ?
N3A C11 S1 . . 122.9(3) ?
N2A C11 S1 . . 115.1(3) ?
N1 C2 C3 . . 104.0(3) ?
N1 C2 H2A . . 111.0 ?
C3 C2 H2A . . 111.0 ?
N1 C2 H2B . . 111.0 ?
C3 C2 H2B . . 111.0 ?
H2A C2 H2B . . 109.0 ?
O1 C1 N1 . . 126.5(4) ?
O1 C1 C4 . . 124.6(4) ?
N1 C1 C4 . . 108.8(3) ?
C9 C10 C5 . . 119.4(4) ?
C9 C10 H10 . . 120.3 ?
C5 C10 H10 . . 120.3 ?
C7 C8 C9 . . 118.0(4) ?
C7 C8 H8 . . 121.0 ?
C9 C8 H8 . . 121.0 ?
C8 C7 C6 . . 121.9(4) ?
C8 C7 Cl1 . . 119.1(3) ?
C6 C7 Cl1 . . 119.0(3) ?
C10 C9 C8 . . 121.8(4) ?
C10 C9 H9 . . 119.1 ?
C8 C9 H9 . . 119.1 ?
C2 C3 C4 . . 104.7(3) ?
C2 C3 H3A . . 110.8 ?
C4 C3 H3A . . 110.8 ?
C2 C3 H3B . . 110.8 ?
C4 C3 H3B . . 110.8 ?
H3A C3 H3B . . 108.9 ?
C11 N2A H2AA . . 120.0 ?
C11 N2A H2AB . . 120.0 ?
H2AA N2A H2AB . . 120.0 ?
C1 N1 C5 . . 126.8(3) ?
C1 N1 C2 . . 112.1(3) ?
C5 N1 C2 . . 120.9(3) ?
C11 N3A H3AA . . 120.0 ?
C11 N3A H3AB . . 120.0 ?
H3AA N3A H3AB . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.749(4) ?
S1 C4 . 1.822(4) ?
Cl1 C7 . 1.737(4) ?
O1 C1 . 1.228(4) ?
C5 C6 . 1.389(5) ?
C5 C10 . 1.392(5) ?
C5 N1 . 1.418(4) ?
C6 C7 . 1.374(5) ?
C6 H6 . 0.9500 ?
C4 C1 . 1.514(5) ?
C4 C3 . 1.523(5) ?
C4 H4 . 1.0000 ?
C11 N3A . 1.296(5) ?
C11 N2A . 1.312(5) ?
C2 N1 . 1.475(5) ?
C2 C3 . 1.520(5) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C1 N1 . 1.363(5) ?
C10 C9 . 1.379(6) ?
C10 H10 . 0.9500 ?
C8 C7 . 1.371(6) ?
C8 C9 . 1.380(6) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
N2A H2AA . 0.8800 ?
N2A H2AB . 0.8800 ?
N3A H3AA . 0.8800 ?
N3A H3AB . 0.8800 ?
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
N2A H2AB Br1 . 0.88 2.43 3.290(3) 165.9
N2A H2AA Br1 1_545 0.88 2.68 3.452(3) 146.8
N2A H2AA Br1 2_646 0.88 2.91 3.426(3) 119.3
N3A H3AA Br1 1_545 0.88 2.44 3.273(3) 157.9
N3A H3AB O1 . 0.88 2.12 2.823(4) 136.6
C2 H2A O1 1_565 0.99 2.57 3.352(5) 137
C3 H3B Br1 4_565 0.99 3.01 3.737(4) 131
C10 H10 O1 . 0.95 2.22 2.852(5) 123.5
