#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227952.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_2227952
loop_
_publ_author_name
'Yang, Yunxia'
_publ_section_title
;
 Tripropylammonium trithiocyanurate
;
_journal_coeditor_code           RN2070
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2793
_journal_paper_doi               10.1107/S1600536810038924
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H22 N +, C3 H2 N3 S3 -'
_chemical_formula_moiety         'C9 H22 N +, C3 H2 N3 S3 -'
_chemical_formula_sum            'C12 H24 N4 S3'
_chemical_formula_weight         320.53
_chemical_name_common
;
Tripropylammonium trithiocyanurate
;
_chemical_name_systematic
;
Tripropylazanium 2,4,6-trisulfanylidenecyclohexan-1-ide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3677(5)
_cell_length_b                   12.8827(8)
_cell_length_c                   16.5339(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1782.33(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5690
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.9188
_exptl_absorpt_correction_T_min  0.7880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.199
_refine_ls_abs_structure_details
'Flack & Bernardinelli (2000), 1316 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0350
_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)+(0.0570P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                3232
_reflns_number_total             3675
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rn2070.cif
_cod_data_source_block           I
_cod_database_code               2227952
_cod_database_fobs_code          2227952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
N N4 0.25770(18) 0.02494(16) 0.48456(11) 0.0513(4) Uani d D 1 . .
H H4 0.307(3) 0.020(2) 0.5345(9) 0.077 Uiso d D 1 . .
C C4 0.3656(3) 0.0945(2) 0.43528(14) 0.0603(6) Uani d . 1 . .
H H4A 0.3771 0.1602 0.4634 0.072 Uiso calc R 1 . .
H H4B 0.4706 0.0629 0.4324 0.072 Uiso calc R 1 . .
C C5 0.3087(3) 0.1159(2) 0.35052(17) 0.0726(7) Uani d . 1 . .
H H5A 0.2116 0.1570 0.3525 0.087 Uiso calc R 1 . .
H H5B 0.2843 0.0509 0.3237 0.087 Uiso calc R 1 . .
C C7 0.2386(3) -0.0818(2) 0.44928(15) 0.0596(5) Uani d . 1 . .
H H7A 0.1680 -0.0775 0.4029 0.072 Uiso calc R 1 . .
H H7B 0.1872 -0.1259 0.4891 0.072 Uiso calc R 1 . .
C C8 0.3920(3) -0.1327(2) 0.42319(19) 0.0756(7) Uani d . 1 . .
H H8A 0.4343 -0.0967 0.3763 0.091 Uiso calc R 1 . .
H H8B 0.4700 -0.1275 0.4664 0.091 Uiso calc R 1 . .
C C9 0.3658(6) -0.2448(3) 0.4026(3) 0.1228(14) Uani d . 1 . .
H H9A 0.4652 -0.2754 0.3862 0.184 Uiso calc R 1 . .
H H9B 0.2899 -0.2500 0.3593 0.184 Uiso calc R 1 . .
H H9C 0.3255 -0.2807 0.4492 0.184 Uiso calc R 1 . .
C C10 0.0991(2) 0.0762(2) 0.50164(16) 0.0605(5) Uani d . 1 . .
H H10A 0.1181 0.1469 0.5194 0.073 Uiso calc R 1 . .
H H10B 0.0380 0.0794 0.4518 0.073 Uiso calc R 1 . .
C C11 0.0026(4) 0.0216(3) 0.5642(2) 0.0995(11) Uani d . 1 . .
H H11A -0.0111 -0.0501 0.5476 0.119 Uiso calc R 1 . .
H H11B 0.0620 0.0215 0.6145 0.119 Uiso calc R 1 . .
C C12 -0.1564(4) 0.0668(4) 0.5792(3) 0.1253(15) Uani d . 1 . .
H H12A -0.2104 0.0272 0.6201 0.188 Uiso calc R 1 . .
H H12B -0.2178 0.0655 0.5302 0.188 Uiso calc R 1 . .
H H12C -0.1446 0.1373 0.5972 0.188 Uiso calc R 1 . .
C C6 0.4346(4) 0.1736(3) 0.3029(2) 0.1079(12) Uani d . 1 . .
H H6A 0.3962 0.1865 0.2492 0.162 Uiso calc R 1 . .
H H6B 0.5302 0.1325 0.3003 0.162 Uiso calc R 1 . .
H H6C 0.4576 0.2385 0.3291 0.162 Uiso calc R 1 . .
N N1 0.5530(2) -0.05504(13) 0.74298(10) 0.0468(4) Uani d D 1 . .
H H1 0.579(3) -0.1170(12) 0.7667(15) 0.070 Uiso d D 1 . .
N N2 0.5353(2) 0.12080(13) 0.74422(11) 0.0456(4) Uani d D 1 . .
H H2 0.556(3) 0.1813(12) 0.7704(14) 0.068 Uiso d D 1 . .
N N3 0.40788(18) 0.02890(11) 0.64040(10) 0.0449(3) Uani d . 1 . .
S S1 0.40179(9) -0.17606(4) 0.63935(4) 0.06707(19) Uani d . 1 . .
C C1 0.4565(2) -0.05976(15) 0.67496(12) 0.0451(4) Uani d . 1 . .
S S2 0.37526(8) 0.23360(4) 0.63897(4) 0.06029(17) Uani d . 1 . .
C C2 0.5970(2) 0.03521(15) 0.77943(11) 0.0433(4) Uani d . 1 . .
S S3 0.71163(7) 0.03940(5) 0.86074(4) 0.06204(17) Uani d . 1 . .
C C3 0.4425(2) 0.12015(15) 0.67552(13) 0.0433(4) Uani d . 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'
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N4 C10 . . 112.32(16) ?
C7 N4 C4 . . 113.42(18) ?
C10 N4 C4 . . 111.51(19) ?
C7 N4 H4 . . 109.2(19) ?
C10 N4 H4 . . 104.8(17) ?
C4 N4 H4 . . 104.9(17) ?
C5 C4 N4 . . 114.92(18) ?
C5 C4 H4A . . 108.5 ?
N4 C4 H4A . . 108.5 ?
C5 C4 H4B . . 108.5 ?
N4 C4 H4B . . 108.5 ?
H4A C4 H4B . . 107.5 ?
C4 C5 C6 . . 110.7(2) ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
N4 C7 C8 . . 114.8(2) ?
N4 C7 H7A . . 108.6 ?
C8 C7 H7A . . 108.6 ?
N4 C7 H7B . . 108.6 ?
C8 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.5 ?
C9 C8 C7 . . 111.1(3) ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
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 ?
C11 C10 N4 . . 113.6(2) ?
C11 C10 H10A . . 108.9 ?
N4 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
N4 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C10 . . 114.8(3) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C2 N1 C1 . . 123.70(17) ?
C2 N1 H1 . . 119.4(17) ?
C1 N1 H1 . . 116.6(17) ?
C2 N2 C3 . . 124.54(17) ?
C2 N2 H2 . . 115.0(17) ?
C3 N2 H2 . . 120.4(17) ?
C1 N3 C3 . . 119.75(16) ?
N3 C1 N1 . . 119.04(17) ?
N3 C1 S1 . . 121.99(15) ?
N1 C1 S1 . . 118.96(15) ?
N2 C2 N1 . . 113.81(16) ?
N2 C2 S3 . . 123.12(15) ?
N1 C2 S3 . . 123.06(15) ?
N3 C3 N2 . . 118.95(17) ?
N3 C3 S2 . . 122.30(15) ?
N2 C3 S2 . . 118.75(15) ?
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
N4 C7 . 1.503(3) ?
N4 C10 . 1.509(3) ?
N4 C4 . 1.511(3) ?
N4 H4 . 0.925(10) ?
C4 C5 . 1.506(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.510(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C7 C8 . 1.504(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.499(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.489(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.474(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
N1 C2 . 1.360(3) ?
N1 C1 . 1.386(3) ?
N1 H1 . 0.915(10) ?
N2 C2 . 1.350(2) ?
N2 C3 . 1.376(3) ?
N2 H2 . 0.908(10) ?
N3 C1 . 1.341(2) ?
N3 C3 . 1.343(2) ?
S1 C1 . 1.674(2) ?
S2 C3 . 1.679(2) ?
C2 S3 . 1.6525(19) ?
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
N4 H4 N3 . 0.925(10) 1.947(11) 2.867(2) 172(3)
N1 H1 S2 3_646 0.915(10) 2.507(12) 3.4037(17) 167(2)
N2 H2 S1 3_656 0.908(10) 2.393(11) 3.2911(17) 170(2)
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
C7 N4 C4 C5 . . . . 61.7(3) ?
C10 N4 C4 C5 . . . . -66.3(3) ?
N4 C4 C5 C6 . . . . -172.3(3) ?
C10 N4 C7 C8 . . . . 174.1(2) ?
C4 N4 C7 C8 . . . . 46.6(3) ?
N4 C7 C8 C9 . . . . 170.0(3) ?
C7 N4 C10 C11 . . . . 63.9(3) ?
C4 N4 C10 C11 . . . . -167.5(2) ?
N4 C10 C11 C12 . . . . -177.1(3) ?
C3 N3 C1 N1 . . . . -5.2(3) ?
C3 N3 C1 S1 . . . . 173.75(16) ?
C2 N1 C1 N3 . . . . 2.8(3) ?
C2 N1 C1 S1 . . . . -176.22(15) ?
C3 N2 C2 N1 . . . . -3.0(3) ?
C3 N2 C2 S3 . . . . 178.48(15) ?
C1 N1 C2 N2 . . . . 1.3(3) ?
C1 N1 C2 S3 . . . . 179.77(16) ?
C1 N3 C3 N2 . . . . 3.6(3) ?
C1 N3 C3 S2 . . . . -175.92(16) ?
C2 N2 C3 N3 . . . . 0.7(3) ?
C2 N2 C3 S2 . . . . -179.76(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656300
