#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/46/7204661.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_7204661
loop_
_publ_author_name
'Babb, Jennifer E. V.'
'Burke, Nichola J.'
'Burrows, Andrew D.'
'Mahon, Mary F.'
'Slade, David M. K.'
_publ_section_title
;
 Hydrogen-bonded linear thiourea hexads in tetra-n-butylammonium
 terephthalate inclusion compounds
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              226
_journal_paper_doi               10.1039/b304010k
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C18 H44 Br N5 S2'
_chemical_formula_weight         474.61
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   16.7880(2)
_cell_length_b                   17.0600(2)
_cell_length_c                   18.3130(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     5244.90(12)
_computing_data_reduction        'Denzo and Scalepack (otwinowski & Minor, 1997'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            93507
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0455
_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)+(0.0618P)²+3.4605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                4246
_reflns_number_total             5986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304010k.txt
_cod_data_source_block           compound3_h01dmks2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7204661
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35927(2) 0.146535(19) 0.506763(16) 0.05617(14) Uani 1 1 d . . .
S2 S 0.22381(4) 0.13530(4) 0.78500(4) 0.03987(17) Uani 1 1 d . . .
S3 S 0.23579(5) 0.11340(4) 0.22480(4) 0.0545(2) Uani 1 1 d . . .
N1 N 0.49426(12) 0.31758(14) 0.33142(12) 0.0444(5) Uani 1 1 d . . .
N2 N 0.28148(13) 0.20488(12) 0.66648(13) 0.0437(5) Uani 1 1 d . . .
H2A H 0.3005 0.2047 0.6217 0.052 Uiso 1 1 calc R . .
H2B H 0.2763 0.2494 0.6902 0.052 Uiso 1 1 calc R . .
N3 N 0.26989(15) 0.07253(13) 0.65929(12) 0.0473(6) Uani 1 1 d . . .
H3A H 0.2891 0.0752 0.6147 0.057 Uiso 1 1 calc R . .
H3B H 0.2569 0.0268 0.6781 0.057 Uiso 1 1 calc R . .
N4 N 0.26583(15) 0.18538(13) 0.35033(13) 0.0495(6) Uani 1 1 d . . .
H4A H 0.2801 0.1863 0.3966 0.059 Uiso 1 1 calc R . .
H4B H 0.2531 0.2293 0.3279 0.059 Uiso 1 1 calc R . .
N5 N 0.28340(15) 0.05367(13) 0.35123(14) 0.0536(6) Uani 1 1 d . . .
H5A H 0.2974 0.0572 0.3974 0.064 Uiso 1 1 calc R . .
H5B H 0.2826 0.0077 0.3294 0.064 Uiso 1 1 calc R . .
C1 C 0.42273(15) 0.33291(18) 0.38017(16) 0.0484(7) Uani 1 1 d . . .
H1A H 0.3760 0.3428 0.3485 0.063 Uiso 1 1 calc R . .
H1B H 0.4116 0.2846 0.4083 0.063 Uiso 1 1 calc R . .
C2 C 0.43000(17) 0.4000(2) 0.43322(18) 0.0595(8) Uani 1 1 d . . .
H1 H 0.4786 0.3935 0.4633 0.077 Uiso 1 1 calc R . .
H2 H 0.4345 0.4501 0.4062 0.077 Uiso 1 1 calc R . .
C3 C 0.3573(2) 0.4017(3) 0.4819(2) 0.0771(11) Uani 1 1 d . . .
H3 H 0.3091 0.4029 0.4508 0.100 Uiso 1 1 calc R . .
H4 H 0.3557 0.3527 0.5108 0.100 Uiso 1 1 calc R . .
C4 C 0.3549(3) 0.4704(3) 0.5332(3) 0.0987(15) Uani 1 1 d . . .
H4C H 0.3066 0.4675 0.5632 0.148 Uiso 1 1 calc R . .
H4D H 0.3545 0.5192 0.5051 0.148 Uiso 1 1 calc R . .
H4E H 0.4019 0.4693 0.5649 0.148 Uiso 1 1 calc R . .
C5 C 0.46925(16) 0.25296(16) 0.27968(16) 0.0465(6) Uani 1 1 d . . .
H5 H 0.4222 0.2713 0.2519 0.060 Uiso 1 1 calc R . .
H6 H 0.4522 0.2073 0.3091 0.060 Uiso 1 1 calc R . .
C6 C 0.53170(19) 0.22549(19) 0.22540(17) 0.0560(8) Uani 1 1 d . . .
H6A H 0.5571 0.2715 0.2022 0.073 Uiso 1 1 calc R . .
H6B H 0.5735 0.1956 0.2514 0.073 Uiso 1 1 calc R . .
C7 C 0.4942(2) 0.17400(19) 0.16699(19) 0.0600(8) Uani 1 1 d . . .
H7A H 0.4603 0.1341 0.1909 0.078 Uiso 1 1 calc R . .
H7B H 0.4595 0.2067 0.1357 0.078 Uiso 1 1 calc R . .
C8 C 0.5546(3) 0.1334(2) 0.1198(2) 0.0813(11) Uani 1 1 d . . .
H8A H 0.5271 0.1009 0.0835 0.122 Uiso 1 1 calc R . .
H8B H 0.5886 0.1001 0.1503 0.122 Uiso 1 1 calc R . .
H8C H 0.5874 0.1726 0.0948 0.122 Uiso 1 1 calc R . .
C9 C 0.56726(16) 0.2937(2) 0.37582(16) 0.0534(7) Uani 1 1 d . . .
H9A H 0.6107 0.2801 0.3415 0.069 Uiso 1 1 calc R . .
H9B H 0.5851 0.3395 0.4046 0.069 Uiso 1 1 calc R . .
C10 C 0.5556(2) 0.2263(3) 0.4268(2) 0.0915(15) Uani 1 1 d . . .
H10A H 0.5341 0.1811 0.3992 0.119 Uiso 1 1 calc R . .
H10B H 0.5158 0.2410 0.4643 0.119 Uiso 1 1 calc R . .
C11 C 0.6321(2) 0.2023(3) 0.4641(2) 0.0855(13) Uani 1 1 d . . .
H11A H 0.6696 0.1825 0.4267 0.111 Uiso 1 1 calc R . .
H11B H 0.6564 0.2492 0.4867 0.111 Uiso 1 1 calc R . .
C12 C 0.6216(3) 0.1413(4) 0.5210(3) 0.141(3) Uani 1 1 d . . .
H12A H 0.6735 0.1287 0.5427 0.212 Uiso 1 1 calc R . .
H12B H 0.5989 0.0940 0.4989 0.212 Uiso 1 1 calc R . .
H12C H 0.5857 0.1608 0.5590 0.212 Uiso 1 1 calc R . .
C13 C 0.51873(18) 0.39099(17) 0.28984(16) 0.0508(7) Uani 1 1 d . B .
H13A H 0.5333 0.4317 0.3259 0.066 Uiso 1 1 calc R . .
H13B H 0.5673 0.3786 0.2614 0.066 Uiso 1 1 calc R . .
C14 C 0.4581(3) 0.4254(2) 0.2385(2) 0.0744(11) Uani 1 1 d . . .
H14A H 0.4468 0.3850 0.2011 0.097 Uiso 1 1 calc R A 1
H14B H 0.4084 0.4325 0.2669 0.097 Uiso 1 1 calc R A 1
C15A C 0.5155(5) 0.4819(4) 0.1908(5) 0.0540(17) Uani 0.50 1 d P B 2
H15A H 0.4986 0.5363 0.2017 0.065 Uiso 0.50 1 calc PR B 2
H15B H 0.5696 0.4759 0.2115 0.065 Uiso 0.50 1 calc PR B 2
C17 C 0.26051(15) 0.13760(14) 0.69835(15) 0.0373(5) Uani 1 1 d . . .
C18 C 0.26349(16) 0.11778(15) 0.31437(16) 0.0430(6) Uani 1 1 d . . .
C16A C 0.5220(5) 0.4789(4) 0.1348(5) 0.0652(18) Uani 0.50 1 d P B 2
H16A H 0.5598 0.5191 0.1187 0.098 Uiso 0.50 1 calc PR B 2
H16B H 0.4703 0.4878 0.1114 0.098 Uiso 0.50 1 calc PR B 2
H16C H 0.5420 0.4269 0.1213 0.098 Uiso 0.50 1 calc PR B 2
C16 C 0.4667(4) 0.5230(4) 0.1319(4) 0.0606(17) Uani 0.50 1 d P B 1
H16D H 0.4835 0.5779 0.1276 0.091 Uiso 0.50 1 calc PR B 1
H16E H 0.4113 0.5180 0.1159 0.091 Uiso 0.50 1 calc PR B 1
H16F H 0.5008 0.4901 0.1011 0.091 Uiso 0.50 1 calc PR B 1
C15 C 0.4727(6) 0.5011(4) 0.1983(5) 0.064(2) Uani 0.50 1 d P B 1
H15C H 0.4396 0.5395 0.2250 0.077 Uiso 0.50 1 calc PR B 1
H15D H 0.5284 0.5143 0.2110 0.077 Uiso 0.50 1 calc PR B 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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 105.9(2) . . ?
C5 N1 C13 111.2(2) . . ?
C1 N1 C13 111.4(2) . . ?
C5 N1 C9 111.2(2) . . ?
C1 N1 C9 111.6(2) . . ?
C13 N1 C9 105.7(2) . . ?
C2 C1 N1 116.5(2) . . ?
C3 C2 C1 109.2(3) . . ?
C4 C3 C2 113.9(4) . . ?
N1 C5 C6 116.3(2) . . ?
C7 C6 C5 110.7(3) . . ?
C8 C7 C6 113.1(3) . . ?
C10 C9 N1 115.7(2) . . ?
C9 C10 C11 112.3(3) . . ?
C12 C11 C10 114.0(4) . . ?
C14 C13 N1 116.8(2) . . ?
C15 C14 C13 121.9(5) . . ?
C15 C14 C15A 29.4(3) . . ?
C13 C14 C15A 99.6(4) . . ?
C16A C15A C14 124.7(7) . . ?
N3 C17 N2 116.8(3) . . ?
N3 C17 S2 121.7(2) . . ?
N2 C17 S2 121.5(2) . . ?
N4 C18 N5 117.1(3) . . ?
N4 C18 S3 121.5(2) . . ?
N5 C18 S3 121.4(2) . . ?
C16 C15 C14 134.8(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C17 1.703(3) . ?
S3 C18 1.707(3) . ?
N1 C5 1.513(4) . ?
N1 C1 1.519(3) . ?
N1 C13 1.522(4) . ?
N1 C9 1.526(3) . ?
N2 C17 1.335(3) . ?
N3 C17 1.330(3) . ?
N4 C18 1.329(4) . ?
N5 C18 1.328(3) . ?
C1 C2 1.507(4) . ?
C2 C3 1.511(4) . ?
C3 C4 1.503(6) . ?
C5 C6 1.519(4) . ?
C6 C7 1.521(4) . ?
C7 C8 1.501(5) . ?
C9 C10 1.493(5) . ?
C10 C11 1.511(4) . ?
C11 C12 1.484(7) . ?
C13 C14 1.505(5) . ?
C14 C15 1.507(8) . ?
C14 C15A 1.619(8) . ?
C15A C16A 1.032(10) . ?
C16 C15 1.276(11) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195478
