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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/70/1507096.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_1507096
loop_
_publ_author_name
'Kim, Su Jeong'
'Jo, Moon-Gi'
'Lee, Jin Yong'
'Kim, Byeang Hyean'
_publ_section_title
;
 Hydrogen bonding patterns of calix[4]arenes with thiourea functionalities
 in solution and in the solid state.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              1963
_journal_page_last               1966
_journal_paper_doi               10.1021/ol049497y
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C44 H56 N4 O4 S2'
_chemical_formula_weight         769.05
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 99.367(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.021(4)
_cell_length_b                   9.4409(16)
_cell_length_c                   17.902(3)
_cell_measurement_temperature    223(2)
_cell_volume                     4172.4(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0942
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8534
_diffrn_reflns_theta_full        23.00
_diffrn_reflns_theta_max         23.00
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_correction_T_min  0.9628
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0983
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1292P)²+24.0159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2502
_refine_ls_wR_factor_ref         0.2745
_reflns_number_gt                2043
_reflns_number_total             2908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol049497ysi20040430_115732.cif
_cod_data_source_block           c2c
_cod_database_code               1507096
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S1 S 0.26289(7) 0.6719(2) 0.11600(10) 0.0564(6) Uani 1 1 d .
O1 O 0.06048(16) 0.2066(4) -0.1885(2) 0.0411(11) Uani 1 1 d .
N1 N 0.2114(2) 0.4259(6) 0.1000(3) 0.0507(15) Uani 1 1 d .
H1D H 0.1876 0.3699 0.0741 0.061 Uiso 1 1 calc R
C1 C 0.2376(3) 0.3779(8) 0.1745(4) 0.062(2) Uani 1 1 d .
H1A H 0.2239 0.2850 0.1847 0.093 Uiso 1 1 calc R
H1B H 0.2299 0.4442 0.2127 0.093 Uiso 1 1 calc R
H1C H 0.2764 0.3727 0.1755 0.093 Uiso 1 1 calc R
O2 O 0.07423(15) 0.1764(4) -0.3623(2) 0.0379(11) Uani 1 1 d .
N2 N 0.19550(19) 0.5744(6) -0.0022(3) 0.0436(14) Uani 1 1 d .
H2A H 0.2007 0.6572 -0.0212 0.052 Uiso 1 1 calc R
C2 C 0.2211(2) 0.5487(7) 0.0691(4) 0.0410(16) Uani 1 1 d .
C3 C 0.1608(2) 0.4791(6) -0.0494(3) 0.0352(14) Uani 1 1 d .
C4 C 0.1139(2) 0.4275(6) -0.0272(3) 0.0355(15) Uani 1 1 d .
H4A H 0.1049 0.4546 0.0197 0.043 Uiso 1 1 calc R
C5 C 0.0800(2) 0.3363(6) -0.0738(3) 0.0340(14) Uani 1 1 d .
C6 C 0.0943(2) 0.2946(6) -0.1425(3) 0.0335(14) Uani 1 1 d .
C7 C 0.1393(2) 0.3524(6) -0.1679(3) 0.0328(14) Uani 1 1 d .
C8 C 0.1726(2) 0.4414(6) -0.1194(3) 0.0382(15) Uani 1 1 d .
H8A H 0.2042 0.4771 -0.1347 0.046 Uiso 1 1 calc R
C9 C 0.0242(2) 0.2954(6) -0.0568(3) 0.0370(15) Uani 1 1 d .
H9A H 0.0179 0.1942 -0.0666 0.044 Uiso 1 1 calc R
H9B H 0.0226 0.3132 -0.0033 0.044 Uiso 1 1 calc R
C10 C 0.0795(4) 0.0597(10) -0.1905(5) 0.088(3) Uani 1 1 d .
H10A H 0.0675 0.0216 -0.2414 0.106 Uiso 1 1 calc R
H10B H 0.1192 0.0599 -0.1816 0.106 Uiso 1 1 calc R
C11 C 0.0617(4) -0.0308(11) -0.1381(6) 0.103(3) Uani 1 1 d .
H11A H 0.0220 -0.0299 -0.1454 0.124 Uiso 1 1 calc R
H11B H 0.0752 0.0029 -0.0868 0.124 Uiso 1 1 calc R
C12 C 0.0819(4) -0.1849(8) -0.1474(6) 0.079(3) Uani 1 1 d .
H12A H 0.0689 -0.2460 -0.1106 0.119 Uiso 1 1 calc R
H12B H 0.1212 -0.1860 -0.1392 0.119 Uiso 1 1 calc R
H12C H 0.0682 -0.2186 -0.1980 0.119 Uiso 1 1 calc R
C13 C 0.1478(2) 0.3260(7) -0.2486(3) 0.0361(14) Uani 1 1 d .
H13A H 0.1478 0.2239 -0.2586 0.043 Uiso 1 1 calc R
H13B H 0.1829 0.3644 -0.2562 0.043 Uiso 1 1 calc R
C14 C 0.1027(2) 0.3969(6) -0.3029(3) 0.0329(14) Uani 1 1 d .
C15 C 0.0657(2) 0.3208(6) -0.3539(3) 0.0317(14) Uani 1 1 d .
C16 C 0.0194(2) 0.3809(6) -0.3941(3) 0.0300(14) Uani 1 1 d .
C17 C 0.0124(2) 0.5261(7) -0.3849(3) 0.0392(15) Uani 1 1 d .
H17A H -0.0186 0.5702 -0.4116 0.047 Uiso 1 1 calc R
C18 C 0.0497(2) 0.6070(7) -0.3380(4) 0.0431(16) Uani 1 1 d .
H18A H 0.0449 0.7053 -0.3342 0.052 Uiso 1 1 calc R
C19 C 0.0938(2) 0.5418(7) -0.2969(3) 0.0384(15) Uani 1 1 d .
H19A H 0.1187 0.5962 -0.2638 0.046 Uiso 1 1 calc R
C20 C 0.1097(3) 0.1465(8) -0.4159(4) 0.061(2) Uani 1 1 d .
H20A H 0.1425 0.2045 -0.4046 0.073 Uiso 1 1 calc R
H20B H 0.0915 0.1696 -0.4672 0.073 Uiso 1 1 calc R
C21 C 0.1249(5) -0.0109(10) -0.4113(7) 0.122(5) Uani 1 1 d .
H21A H 0.1374 -0.0368 -0.3583 0.147 Uiso 1 1 calc R
H21B H 0.0927 -0.0679 -0.4300 0.147 Uiso 1 1 calc R
C22 C 0.1678(5) -0.0427(13) -0.4564(7) 0.123(4) Uani 1 1 d .
H22A H 0.1763 -0.1429 -0.4528 0.184 Uiso 1 1 calc R
H22B H 0.1999 0.0119 -0.4372 0.184 Uiso 1 1 calc R
H22C H 0.1553 -0.0178 -0.5089 0.184 Uiso 1 1 calc R
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'
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'
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
C6 O1 C10 114.8(5) . .
C2 N1 C1 124.6(6) . .
C2 N1 H1D 117.7 . .
C1 N1 H1D 117.7 . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C15 O2 C20 112.8(5) . .
C2 N2 C3 126.4(5) . .
C2 N2 H2A 116.8 . .
C3 N2 H2A 116.8 . .
N1 C2 N2 117.4(5) . .
N1 C2 S1 122.3(5) . .
N2 C2 S1 120.3(5) . .
C8 C3 C4 119.0(5) . .
C8 C3 N2 120.0(5) . .
C4 C3 N2 121.0(5) . .
C5 C4 C3 120.6(6) . .
C5 C4 H4A 119.7 . .
C3 C4 H4A 119.7 . .
C4 C5 C6 119.1(5) . .
C4 C5 C9 121.8(5) . .
C6 C5 C9 118.6(5) . .
O1 C6 C7 119.8(5) . .
O1 C6 C5 118.9(5) . .
C7 C6 C5 121.1(5) . .
C8 C7 C6 118.0(5) . .
C8 C7 C13 122.2(5) . .
C6 C7 C13 119.6(5) . .
C3 C8 C7 122.0(6) . .
C3 C8 H8A 119.0 . .
C7 C8 H8A 119.0 . .
C16 C9 C5 110.2(5) 2_554 .
C16 C9 H9A 109.6 2_554 .
C5 C9 H9A 109.6 . .
C16 C9 H9B 109.6 2_554 .
C5 C9 H9B 109.6 . .
H9A C9 H9B 108.1 . .
C11 C10 O1 115.0(9) . .
C11 C10 H10A 108.5 . .
O1 C10 H10A 108.5 . .
C11 C10 H10B 108.5 . .
O1 C10 H10B 108.5 . .
H10A C10 H10B 107.5 . .
C10 C11 C12 110.8(10) . .
C10 C11 H11A 109.5 . .
C12 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
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 . .
C7 C13 C14 109.4(5) . .
C7 C13 H13A 109.8 . .
C14 C13 H13A 109.8 . .
C7 C13 H13B 109.8 . .
C14 C13 H13B 109.8 . .
H13A C13 H13B 108.2 . .
C15 C14 C19 117.4(5) . .
C15 C14 C13 122.6(5) . .
C19 C14 C13 119.7(5) . .
C16 C15 O2 118.5(5) . .
C16 C15 C14 122.8(5) . .
O2 C15 C14 118.6(5) . .
C15 C16 C17 116.9(5) . .
C15 C16 C9 123.1(5) . 2_554
C17 C16 C9 120.0(5) . 2_554
C18 C17 C16 122.1(6) . .
C18 C17 H17A 119.0 . .
C16 C17 H17A 119.0 . .
C19 C18 C17 119.0(6) . .
C19 C18 H18A 120.5 . .
C17 C18 H18A 120.5 . .
C18 C19 C14 121.7(6) . .
C18 C19 H19A 119.2 . .
C14 C19 H19A 119.2 . .
O2 C20 C21 109.2(6) . .
O2 C20 H20A 109.8 . .
C21 C20 H20A 109.8 . .
O2 C20 H20B 109.8 . .
C21 C20 H20B 109.8 . .
H20A C20 H20B 108.3 . .
C22 C21 C20 111.3(9) . .
C22 C21 H21A 109.4 . .
C20 C21 H21A 109.4 . .
C22 C21 H21B 109.4 . .
C20 C21 H21B 109.4 . .
H21A C21 H21B 108.0 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.693(6) .
O1 C6 1.363(7) .
O1 C10 1.468(11) .
N1 C2 1.325(8) .
N1 C1 1.459(8) .
N1 H1D 0.8700 .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 H1C 0.9700 .
O2 C15 1.391(7) .
O2 C20 1.437(8) .
N2 C2 1.354(8) .
N2 C3 1.426(7) .
N2 H2A 0.8700 .
C3 C8 1.381(9) .
C3 C4 1.388(8) .
C4 C5 1.387(8) .
C4 H4A 0.9400 .
C5 C6 1.393(8) .
C5 C9 1.526(8) .
C6 C7 1.392(8) .
C7 C8 1.386(8) .
C7 C13 1.515(8) .
C8 H8A 0.9400 .
C9 C16 1.517(8) 2_554
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C10 C11 1.394(13) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C11 C12 1.558(13) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 H12C 0.9700 .
C13 C14 1.518(8) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 C15 1.391(8) .
C14 C19 1.393(8) .
C15 C16 1.382(8) .
C16 C17 1.395(8) .
C16 C9 1.517(8) 2_554
C17 C18 1.380(9) .
C17 H17A 0.9400 .
C18 C19 1.369(8) .
C18 H18A 0.9400 .
C19 H19A 0.9400 .
C20 C21 1.532(12) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 C22 1.476(14) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 H22C 0.9700 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102374253
