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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/18/4501868.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_4501868
loop_
_publ_author_name
'Paisner, Kathryn'
'Zakharov, Lev N.'
'Doxsee, Kenneth M.'
_publ_section_title
;
 A Robust Thiourea Synthon for Crystal Engineering
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3757
_journal_paper_doi               10.1021/cg100589n
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C22 H46 N6 S2'
_chemical_formula_weight         458.77
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                85.891(2)
_cell_angle_beta                 76.883(2)
_cell_angle_gamma                82.603(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5087(9)
_cell_length_b                   9.4482(12)
_cell_length_c                   9.4581(12)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.18
_cell_volume                     647.42(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector Bruker Apex'
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7305
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0388
_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)+(0.0536P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2351
_reflns_number_total             2800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100589n_si_002.cif
_cod_data_source_block           di-n-pentyl_(1b)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.19140(6) 0.56239(4) 0.29176(4) 0.03720(15) Uani 1 1 d
N1 N 0.13615(16) 0.09888(13) -0.01088(12) 0.0269(3) Uani 1 1 d
N2 N 0.12567(18) 0.37221(14) 0.12038(14) 0.0315(3) Uani 1 1 d
N3 N -0.08475(18) 0.40433(14) 0.33429(15) 0.0327(3) Uani 1 1 d
C1 C -0.1552(2) 0.04375(17) -0.05910(17) 0.0307(3) Uani 1 1 d
C2 C 0.0306(2) 0.09390(17) -0.12345(16) 0.0303(3) Uani 1 1 d
C3 C 0.3196(2) 0.14434(18) -0.07466(18) 0.0341(4) Uani 1 1 d
C4 C 0.3153(2) 0.30339(18) -0.11601(17) 0.0357(4) Uani 1 1 d
C5 C 0.2941(2) 0.39593(18) 0.01334(17) 0.0346(4) Uani 1 1 d
C6 C 0.0715(2) 0.43834(15) 0.24626(16) 0.0287(3) Uani 1 1 d
C7 C -0.1987(2) 0.30277(17) 0.30236(17) 0.0308(3) Uani 1 1 d
C8 C -0.3793(2) 0.30532(19) 0.41329(19) 0.0347(4) Uani 1 1 d
C9 C -0.5038(2) 0.20519(18) 0.37778(17) 0.0320(3) Uani 1 1 d
C10 C -0.6816(2) 0.2003(2) 0.49173(19) 0.0374(4) Uani 1 1 d
C11 C -0.8081(3) 0.1026(2) 0.4550(2) 0.0451(4) Uani 1 1 d
H2N H 0.079(2) 0.2996(19) 0.1085(18) 0.036(5) Uiso 1 1 d
H3N H -0.107(2) 0.4304(18) 0.416(2) 0.034(5) Uiso 1 1 d
H1A H -0.223(2) 0.0399(16) -0.1344(17) 0.028(4) Uiso 1 1 d
H1B H -0.230(2) 0.1154(17) 0.0126(18) 0.031(4) Uiso 1 1 d
H2A H 0.013(2) 0.1832(18) -0.1678(17) 0.029(4) Uiso 1 1 d
H2B H 0.100(2) 0.0286(17) -0.1987(17) 0.028(4) Uiso 1 1 d
H3A H 0.392(2) 0.1220(17) -0.0010(18) 0.032(4) Uiso 1 1 d
H3B H 0.376(2) 0.0847(18) -0.158(2) 0.041(5) Uiso 1 1 d
H4A H 0.424(3) 0.3198(18) -0.1802(19) 0.036(4) Uiso 1 1 d
H4B H 0.218(3) 0.3346(18) -0.1689(19) 0.042(5) Uiso 1 1 d
H5A H 0.288(2) 0.498(2) -0.0198(19) 0.041(5) Uiso 1 1 d
H5B H 0.402(2) 0.3713(18) 0.0604(18) 0.037(4) Uiso 1 1 d
H7A H -0.132(2) 0.2077(19) 0.2993(18) 0.036(4) Uiso 1 1 d
H7B H -0.223(2) 0.3261(18) 0.2069(19) 0.039(5) Uiso 1 1 d
H8A H -0.349(3) 0.2779(19) 0.509(2) 0.045(5) Uiso 1 1 d
H8B H -0.440(3) 0.397(2) 0.419(2) 0.051(5) Uiso 1 1 d
H9A H -0.443(2) 0.1055(18) 0.3691(17) 0.033(4) Uiso 1 1 d
H9B H -0.534(2) 0.2324(18) 0.2801(19) 0.040(5) Uiso 1 1 d
H10A H -0.746(3) 0.299(2) 0.500(2) 0.053(5) Uiso 1 1 d
H10B H -0.651(3) 0.1666(19) 0.588(2) 0.047(5) Uiso 1 1 d
H11A H -0.830(3) 0.130(2) 0.357(2) 0.051(5) Uiso 1 1 d
H11B H -0.745(3) 0.002(2) 0.444(2) 0.052(6) Uiso 1 1 d
H11C H -0.922(3) 0.105(2) 0.528(2) 0.068(7) Uiso 1 1 d
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
_geom_angle_site_symmetry_1
C1 N1 C2 108.16(12) 2
C1 N1 C3 110.21(12) 2
C2 N1 C3 110.93(12) .
C6 N2 C5 123.54(13) .
C6 N2 H2N 120.1(12) .
C5 N2 H2N 114.6(12) .
C6 N3 C7 124.79(13) .
C6 N3 H3N 116.9(13) .
C7 N3 H3N 117.2(13) .
N1 C1 C2 111.34(12) 2
N1 C1 H1A 108.1(9) 2
C2 C1 H1A 110.3(9) .
N1 C1 H1B 110.9(9) 2
C2 C1 H1B 109.0(9) .
H1A C1 H1B 107.2(13) .
N1 C2 C1 111.04(12) .
N1 C2 H2A 110.3(10) .
C1 C2 H2A 108.8(10) .
N1 C2 H2B 109.4(9) .
C1 C2 H2B 109.5(9) .
H2A C2 H2B 107.7(13) .
N1 C3 C4 113.77(13) .
N1 C3 H3A 106.3(10) .
C4 C3 H3A 108.6(10) .
N1 C3 H3B 107.4(10) .
C4 C3 H3B 112.4(10) .
H3A C3 H3B 108.0(14) .
C5 C4 C3 113.34(14) .
C5 C4 H4A 107.5(11) .
C3 C4 H4A 109.2(11) .
C5 C4 H4B 110.2(10) .
C3 C4 H4B 110.5(10) .
H4A C4 H4B 105.6(14) .
N2 C5 C4 110.07(13) .
N2 C5 H5A 109.1(10) .
C4 C5 H5A 109.6(10) .
N2 C5 H5B 108.8(10) .
C4 C5 H5B 110.1(10) .
H5A C5 H5B 109.1(14) .
N3 C6 N2 116.76(13) .
N3 C6 S1 121.08(11) .
N2 C6 S1 122.15(11) .
N3 C7 C8 111.37(12) .
N3 C7 H7A 109.5(10) .
C8 C7 H7A 110.5(10) .
N3 C7 H7B 109.2(10) .
C8 C7 H7B 109.2(10) .
H7A C7 H7B 107.0(14) .
C7 C8 C9 112.12(13) .
C7 C8 H8A 107.0(11) .
C9 C8 H8A 110.8(11) .
C7 C8 H8B 110.2(12) .
C9 C8 H8B 109.4(12) .
H8A C8 H8B 107.2(16) .
C8 C9 C10 113.02(13) .
C8 C9 H9A 111.8(10) .
C10 C9 H9A 106.6(9) .
C8 C9 H9B 110.9(10) .
C10 C9 H9B 109.1(10) .
H9A C9 H9B 105.0(13) .
C11 C10 C9 113.16(14) .
C11 C10 H10A 109.3(11) .
C9 C10 H10A 107.8(12) .
C11 C10 H10B 108.9(10) .
C9 C10 H10B 108.8(11) .
H10A C10 H10B 108.8(15) .
C10 C11 H11A 109.0(11) .
C10 C11 H11B 110.5(11) .
H11A C11 H11B 103.4(16) .
C10 C11 H11C 111.0(13) .
H11A C11 H11C 112.0(17) .
H11B C11 H11C 110.6(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C6 1.7000(15) .
N1 C1 1.4628(19) 2
N1 C2 1.4707(19) .
N1 C3 1.4777(18) .
N2 C6 1.3397(19) .
N2 C5 1.4607(19) .
N2 H2N 0.834(18) .
N3 C6 1.337(2) .
N3 C7 1.4543(19) .
N3 H3N 0.807(18) .
C1 N1 1.4628(19) 2
C1 C2 1.512(2) .
C1 H1A 0.970(16) .
C1 H1B 1.013(17) .
C2 H2A 0.922(16) .
C2 H2B 0.986(16) .
C3 C4 1.524(2) .
C3 H3A 0.972(17) .
C3 H3B 0.982(18) .
C4 C5 1.522(2) .
C4 H4A 0.925(18) .
C4 H4B 0.983(19) .
C5 H5A 0.994(18) .
C5 H5B 1.004(18) .
C7 C8 1.513(2) .
C7 H7A 0.970(17) .
C7 H7B 0.967(18) .
C8 C9 1.516(2) .
C8 H8A 0.993(19) .
C8 H8B 0.92(2) .
C9 C10 1.517(2) .
C9 H9A 0.993(17) .
C9 H9B 1.009(18) .
C10 C11 1.516(2) .
C10 H10A 0.99(2) .
C10 H10B 1.005(19) .
C11 H11A 0.99(2) .
C11 H11B 1.01(2) .
C11 H11C 0.97(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N1 0.834(18) 2.221(18) 2.9292(18) 142.8(16) .
N3 H3N S1 0.807(18) 2.691(18) 3.4726(15) 163.5(16) 2_566
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
_geom_torsion_site_symmetry_1
C1 N1 C2 C1 57.56(17) 2
C3 N1 C2 C1 178.54(13) .
N1 C1 C2 N1 -59.41(18) 2
C1 N1 C3 C4 -165.53(13) 2
C2 N1 C3 C4 74.70(17) .
N1 C3 C4 C5 78.06(18) .
C6 N2 C5 C4 179.49(15) .
C3 C4 C5 N2 -57.95(19) .
C7 N3 C6 N2 -0.5(2) .
C7 N3 C6 S1 178.16(12) .
C5 N2 C6 N3 -179.14(14) .
C5 N2 C6 S1 2.2(2) .
C6 N3 C7 C8 -171.42(15) .
N3 C7 C8 C9 177.28(14) .
C7 C8 C9 C10 177.03(15) .
C8 C9 C10 C11 178.83(16) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102045400
