#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229833.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_2229833
loop_
_publ_author_name
'Okuniewski, Andrzej'
'Dabrowska, Agnieszka'
'Chojnacki, Jaroslaw'
_publ_section_title
;
 1,3-Di-n-butylthiourea
;
_journal_coeditor_code           SI2344
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o925
_journal_paper_doi               10.1107/S1600536811009743
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H20 N2 S'
_chemical_formula_moiety         'C9 H20 N2 S'
_chemical_formula_sum            'C9 H20 N2 S'
_chemical_formula_weight         188.33
_chemical_melting_point          336.0(10)
_chemical_name_systematic
;
1,3-Di-n-butylthiourea
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.476(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6395(6)
_cell_length_b                   10.0836(6)
_cell_length_c                   9.0128(5)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.6338
_cell_measurement_theta_min      2.5788
_cell_volume                     1148.66(11)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury
(Macrae et al., 2008)
;
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.1883
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5268
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'[CrysAlis PRO (Oxford Diffraction, 2010; based on Clark & Reid, 1995)]'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.4759
_exptl_crystal_size_mid          0.2847
_exptl_crystal_size_min          0.0876
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                1656
_reflns_number_total             2247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2344.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229833
_cod_database_fobs_code          2229833
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
S S1 0.16510(4) 0.55610(5) 1.03064(5) 0.02246(18) Uani d . 1 . .
N N1 0.03660(13) 0.60898(18) 0.80521(17) 0.0218(4) Uani d D 1 . .
N N2 0.19164(13) 0.72585(17) 0.80620(18) 0.0229(4) Uani d D 1 . .
C C1 0.12922(15) 0.63626(19) 0.8705(2) 0.0209(4) Uani d . 1 . .
C C2 -0.00052(15) 0.6657(2) 0.6656(2) 0.0225(5) Uani d . 1 . .
H H2A 0.0525 0.649 0.5877 0.027 Uiso calc R 1 . .
H H2B -0.0082 0.7629 0.6769 0.027 Uiso calc R 1 . .
C C3 -0.10604(15) 0.6065(2) 0.6181(2) 0.0232(5) Uani d . 1 . .
H H3A -0.1004 0.5086 0.6174 0.028 Uiso calc R 1 . .
H H3B -0.1608 0.6314 0.6909 0.028 Uiso calc R 1 . .
C C4 -0.13954(16) 0.6542(2) 0.4653(2) 0.0260(5) Uani d . 1 . .
H H4A -0.0831 0.6327 0.3938 0.031 Uiso calc R 1 . .
H H4B -0.1475 0.7518 0.4676 0.031 Uiso calc R 1 . .
C C5 -0.24282(17) 0.5926(2) 0.4116(2) 0.0332(5) Uani d . 1 . .
H H5A -0.2359 0.4959 0.4103 0.05 Uiso calc R 1 . .
H H5B -0.259 0.6244 0.3112 0.05 Uiso calc R 1 . .
H H5C -0.3001 0.618 0.4785 0.05 Uiso calc R 1 . .
C C6 0.29696(15) 0.7629(2) 0.8598(2) 0.0239(5) Uani d . 1 . .
H H6A 0.296 0.7677 0.9695 0.029 Uiso calc R 1 . .
H H6B 0.3145 0.8523 0.8218 0.029 Uiso calc R 1 . .
C C7 0.38310(15) 0.6662(2) 0.8128(2) 0.0254(5) Uani d . 1 . .
H H7A 0.365 0.5764 0.8489 0.03 Uiso calc R 1 . .
H H7B 0.3855 0.6629 0.7031 0.03 Uiso calc R 1 . .
C C8 0.49139(17) 0.7044(2) 0.8722(3) 0.0355(6) Uani d . 1 . .
H H8A 0.489 0.7081 0.9819 0.043 Uiso calc R 1 . .
H H8B 0.5097 0.7941 0.8357 0.043 Uiso calc R 1 . .
C C9 0.57675(19) 0.6074(3) 0.8255(3) 0.0469(7) Uani d . 1 . .
H H9A 0.5583 0.5182 0.8596 0.07 Uiso calc R 1 . .
H H9B 0.6446 0.634 0.8697 0.07 Uiso calc R 1 . .
H H9C 0.5824 0.6075 0.7172 0.07 Uiso calc R 1 . .
H H1 -0.0032(14) 0.5586(19) 0.854(2) 0.028(6) Uiso d D 1 . .
H H2 0.1715(15) 0.7675(18) 0.7292(15) 0.019(6) Uiso d D 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 0.0254(3) 0.0207(3) 0.0213(3) 0.0005(2) 0.00074(19) 0.0018(2)
N1 0.0218(9) 0.0250(9) 0.0188(8) -0.0043(8) 0.0011(7) 0.0019(7)
N2 0.0238(9) 0.0227(9) 0.0221(9) -0.0016(7) -0.0019(7) 0.0047(7)
C1 0.0251(10) 0.0180(10) 0.0197(10) 0.0039(8) 0.0051(8) -0.0024(8)
C2 0.0257(10) 0.0213(11) 0.0206(10) 0.0003(9) 0.0037(8) 0.0015(8)
C3 0.0234(10) 0.0223(10) 0.0238(11) -0.0007(8) 0.0013(8) 0.0018(8)
C4 0.0325(12) 0.0223(11) 0.0232(11) -0.0027(9) -0.0003(9) 0.0014(8)
C5 0.0325(12) 0.0355(13) 0.0313(12) -0.0036(10) -0.0068(10) 0.0028(10)
C6 0.0226(10) 0.0219(11) 0.0272(11) -0.0047(9) -0.0010(8) 0.0011(8)
C7 0.0251(11) 0.0280(11) 0.0230(10) 0.0000(9) -0.0003(8) 0.0020(9)
C8 0.0276(12) 0.0329(13) 0.0460(14) -0.0016(10) -0.0010(10) 0.0020(11)
C9 0.0292(13) 0.0475(16) 0.0641(18) 0.0056(12) 0.0016(12) 0.0049(14)
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 0 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-18 -1 -1 0.0438
18 1 1 0.0438
1 -14 2 0.1757
-3 7 11 0.1365
2 5 -12 0.1447
3 -7 -11 0.2968
-1 14 -2 0.1079
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
C1 N1 C2 . . 125.10(17) ?
C1 N1 H1 . . 114.7(15) ?
C2 N1 H1 . . 120.1(15) ?
C1 N2 C6 . . 124.74(17) ?
C1 N2 H2 . . 121.0(14) ?
C6 N2 H2 . . 114.2(14) ?
N1 C1 N2 . . 117.90(18) ?
N1 C1 S1 . . 119.96(15) ?
N2 C1 S1 . . 122.13(15) ?
N1 C2 C3 . . 111.42(16) ?
N1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
N1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108 ?
C4 C3 C2 . . 111.70(16) ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 107.9 ?
C3 C4 C5 . . 113.14(17) ?
C3 C4 H4A . . 109 ?
C5 C4 H4A . . 109 ?
C3 C4 H4B . . 109 ?
C5 C4 H4B . . 109 ?
H4A C4 H4B . . 107.8 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N2 C6 C7 . . 113.32(17) ?
N2 C6 H6A . . 108.9 ?
C7 C6 H6A . . 108.9 ?
N2 C6 H6B . . 108.9 ?
C7 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
C8 C7 C6 . . 112.61(18) ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7B . . 109.1 ?
C6 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C7 C8 C9 . . 112.3(2) ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.9 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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 C1 . 1.712(2) ?
N1 C1 . 1.334(2) ?
N1 C2 . 1.456(2) ?
N1 H1 . 0.844(9) ?
N2 C1 . 1.335(3) ?
N2 C6 . 1.461(3) ?
N2 H2 . 0.849(9) ?
C2 C3 . 1.519(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.515(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.521(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 C7 . 1.524(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.515(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.518(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
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
N1 H1 S1 3_567 0.844(9) 2.575(11) 3.3943(17) 164.0(19)
N2 H2 S1 4_575 0.849(9) 2.524(12) 3.3319(17) 159.4(18)
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 N2 . . . . 2.5(3) ?
C2 N1 C1 S1 . . . . -176.99(15) ?
C6 N2 C1 N1 . . . . -177.36(17) ?
C6 N2 C1 S1 . . . . 2.1(3) ?
C1 N1 C2 C3 . . . . 176.27(17) ?
N1 C2 C3 C4 . . . . -173.97(16) ?
C2 C3 C4 C5 . . . . 177.74(17) ?
C1 N2 C6 C7 . . . . 81.5(2) ?
N2 C6 C7 C8 . . . . -178.71(17) ?
C6 C7 C8 C9 . . . . 179.74(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2005824
