#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:18:34 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516427.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_4516427
loop_
_publ_author_name
'Katzsch, Felix'
'Gruber, Tobias'
'Weber, Edwin'
_publ_section_title
;
 Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring
 Benzo[b]thiophene Units as a Lateral Construction Element
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5047
_journal_paper_doi               10.1021/acs.cgd.5b01034
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C36 H22 O2 S4'
_chemical_formula_sum            'C36 H22 O2 S4'
_chemical_formula_weight         614.78
_chemical_name_systematic
;
 '1,1,4,4-Tetra(benzo[b]thien-2-yl)but-2-yne-1,4-diol dimethyl sulfoxide disolvate'
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.6950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1001(3)
_cell_length_b                   8.4594(2)
_cell_length_c                   23.9058(6)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.05
_cell_measurement_theta_min      2.33
_cell_volume                     2019.06(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19101
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.8877
_exptl_absorpt_correction_T_min  0.8535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.47
_platon_squeeze_details
;
;
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0376
_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)+(0.0412P)²+1.6297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                3272
_reflns_number_total             3541
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            3d.cif
_cod_data_source_block           feka_104_monop
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4516427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35750(13) 0.78174(14) 0.06406(5) 0.0275(3) Uani 1 1 d . . .
H1 H 0.3626 0.7453 0.0318 0.041 Uiso 1 1 calc R . .
S1 S 0.26600(6) 0.99369(7) 0.15044(2) 0.02168(18) Uani 0.912(3) 1 d P A 1
C2 C 0.3666(3) 1.2038(4) 0.09144(13) 0.0240(7) Uani 0.912(3) 1 d P A 1
H2 H 0.4151 1.2519 0.0649 0.029 Uiso 0.912(3) 1 calc PR A 1
S1B S 0.3910(10) 1.2461(10) 0.0814(4) 0.0253(18) Uani 0.088(3) 1 d PU A 2
C2B C 0.294(3) 1.030(3) 0.1379(11) 0.019(2) Uani 0.088(3) 1 d PU A 2
H2B H 0.2785 0.9281 0.1527 0.023 Uiso 0.088(3) 1 calc PR A 2
S2 S 0.54752(5) 0.73993(6) 0.16952(2) 0.03589(16) Uani 1 1 d . A .
C1 C 0.36436(15) 1.0475(2) 0.09963(6) 0.0180(3) Uani 1 1 d U . .
C3 C 0.28930(17) 1.2931(2) 0.12638(7) 0.0243(4) Uani 1 1 d . . .
C4 C 0.2687(2) 1.4551(2) 0.13038(9) 0.0362(5) Uani 1 1 d . A .
H4 H 0.3080 1.5262 0.1069 0.043 Uiso 1 1 calc R . .
C5 C 0.1911(2) 1.5118(2) 0.16859(9) 0.0411(5) Uani 1 1 d . . .
H5 H 0.1776 1.6224 0.1714 0.049 Uiso 1 1 calc R A .
C6 C 0.1319(2) 1.4086(2) 0.20331(8) 0.0355(5) Uani 1 1 d . A .
H6 H 0.0782 1.4498 0.2293 0.043 Uiso 1 1 calc R . .
C7 C 0.15071(18) 1.2476(2) 0.20015(8) 0.0284(4) Uani 1 1 d . . .
H7 H 0.1110 1.1772 0.2237 0.034 Uiso 1 1 calc R A .
C8 C 0.22959(17) 1.1907(2) 0.16146(7) 0.0216(4) Uani 1 1 d . A .
C9 C 0.56399(16) 0.87205(19) 0.11535(7) 0.0196(3) Uani 1 1 d . . .
C10 C 0.69000(17) 0.9275(2) 0.11750(7) 0.0228(4) Uani 1 1 d . A .
H10 H 0.7161 0.9997 0.0907 0.027 Uiso 1 1 calc R . .
C11 C 0.78072(17) 0.8656(2) 0.16470(7) 0.0212(4) Uani 1 1 d . . .
C12 C 0.91684(18) 0.8965(2) 0.18148(8) 0.0277(4) Uani 1 1 d . A .
H12 H 0.9632 0.9652 0.1597 0.033 Uiso 1 1 calc R . .
C13 C 0.98344(19) 0.8269(2) 0.22979(8) 0.0314(4) Uani 1 1 d . . .
H13 H 1.0754 0.8500 0.2417 0.038 Uiso 1 1 calc R A .
C14 C 0.9171(2) 0.7230(3) 0.26133(9) 0.0391(5) Uani 1 1 d . A .
H14 H 0.9649 0.6747 0.2942 0.047 Uiso 1 1 calc R . .
C15 C 0.7838(2) 0.6893(3) 0.24551(10) 0.0448(6) Uani 1 1 d . . .
H15 H 0.7389 0.6184 0.2671 0.054 Uiso 1 1 calc R A .
C16 C 0.71558(18) 0.7613(2) 0.19716(8) 0.0278(4) Uani 1 1 d . A .
C17 C 0.44018(16) 0.91766(19) 0.07394(6) 0.0188(3) Uani 1 1 d . A .
C18 C 0.48282(16) 0.9763(2) 0.02109(7) 0.0202(3) Uani 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'
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
C17 O1 H1 109.5 .
C8 S1 C1 90.63(8) .
C1 C2 C3 114.2(3) .
C1 C2 H2 122.9 .
C3 C2 H2 122.9 .
C3 S1B C1 86.2(4) .
C1 C2B C8 116.6(18) .
C1 C2B H2B 121.7 .
C8 C2B H2B 121.7 .
C16 S2 C9 91.06(8) .
C2B C1 C2 104.6(12) .
C2B C1 C17 125.8(12) .
C2 C1 C17 129.37(19) .
C2 C1 S1 112.63(17) .
C17 C1 S1 117.88(12) .
C2B C1 S1B 114.9(12) .
C17 C1 S1B 118.8(3) .
S1 C1 S1B 123.0(3) .
C4 C3 C8 118.98(17) .
C4 C3 C2 131.0(2) .
C8 C3 C2 110.1(2) .
C4 C3 S1B 113.4(3) .
C8 C3 S1B 127.5(3) .
C5 C4 C3 119.62(18) .
C5 C4 H4 120.2 .
C3 C4 H4 120.2 .
C4 C5 C6 120.93(19) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C7 C6 C5 120.55(18) .
C7 C6 H6 119.7 .
C5 C6 H6 119.7 .
C6 C7 C8 118.34(17) .
C6 C7 H7 120.8 .
C8 C7 H7 120.8 .
C7 C8 C3 121.58(17) .
C7 C8 C2B 143.9(10) .
C3 C8 C2B 94.5(10) .
C7 C8 S1 125.99(14) .
C3 C8 S1 112.44(13) .
C10 C9 C17 127.84(15) .
C10 C9 S2 113.02(13) .
C17 C9 S2 119.07(12) .
C9 C10 C11 112.81(15) .
C9 C10 H10 123.6 .
C11 C10 H10 123.6 .
C12 C11 C16 118.82(16) .
C12 C11 C10 129.69(16) .
C16 C11 C10 111.48(15) .
C13 C12 C11 119.70(17) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
C12 C13 C14 120.62(18) .
C12 C13 H13 119.7 .
C14 C13 H13 119.7 .
C15 C14 C13 120.87(18) .
C15 C14 H14 119.6 .
C13 C14 H14 119.6 .
C14 C15 C16 118.68(19) .
C14 C15 H15 120.7 .
C16 C15 H15 120.7 .
C15 C16 C11 121.29(17) .
C15 C16 S2 127.09(15) .
C11 C16 S2 111.61(13) .
O1 C17 C18 111.67(13) .
O1 C17 C1 109.45(13) .
C18 C17 C1 109.37(13) .
O1 C17 C9 107.91(13) .
C18 C17 C9 108.87(13) .
C1 C17 C9 109.55(13) .
C18 C18 C17 179.8(3) 3_675
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.4197(19) .
O1 H1 0.8400 .
S1 C8 1.7355(18) .
S1 C1 1.7420(16) .
C2 C1 1.337(4) .
C2 C3 1.440(4) .
C2 H2 0.9500 .
S1B C3 1.645(9) .
S1B C1 1.766(8) .
C2B C1 1.25(3) .
C2B C8 1.65(3) .
C2B H2B 0.9500 .
S2 C16 1.7353(19) .
S2 C9 1.7375(16) .
C1 C17 1.521(2) .
C3 C4 1.392(3) .
C3 C8 1.403(2) .
C4 C5 1.376(3) .
C4 H4 0.9500 .
C5 C6 1.400(3) .
C5 H5 0.9500 .
C6 C7 1.379(3) .
C6 H6 0.9500 .
C7 C8 1.394(2) .
C7 H7 0.9500 .
C9 C10 1.350(2) .
C9 C17 1.523(2) .
C10 C11 1.440(2) .
C10 H10 0.9500 .
C11 C12 1.397(2) .
C11 C16 1.403(2) .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 C14 1.394(3) .
C13 H13 0.9500 .
C14 C15 1.373(3) .
C14 H14 0.9500 .
C15 C16 1.393(3) .
C15 H15 0.9500 .
C17 C18 1.481(2) .
C18 C18 1.185(3) 3_675
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
C4 H4 O1 0.95 2.47 3.374(2) 157.9 1_565
C13 H13 Cg1 0.95 2.86 3.6856(19) 145.5 2_645
C14 H14 Cg3 0.95 2.80 3.657(2) 150.4 2_645
C15 H15 Cg5 0.95 2.69 3.629(2) 169.1 2_645
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
C8 C2B C1 C2 1.9(17)
C8 C2B C1 C17 176.2(7)
C8 C2B C1 S1 -165(9)
C8 C2B C1 S1B 4(2)
C3 C2 C1 C2B -1.4(11)
C3 C2 C1 C17 -175.42(17)
C3 C2 C1 S1 0.6(3)
C3 C2 C1 S1B -170(3)
C8 S1 C1 C2B 12(8)
C8 S1 C1 C2 -0.95(18)
C8 S1 C1 C17 175.55(12)
C8 S1 C1 S1B 1.2(4)
C3 S1B C1 C2B -4.2(13)
C3 S1B C1 C2 8(2)
C3 S1B C1 C17 -176.8(2)
C3 S1B C1 S1 -2.5(6)
C1 C2 C3 C4 179.3(2)
C1 C2 C3 C8 0.2(3)
C1 C2 C3 S1B 173.3(17)
C1 S1B C3 C4 -179.7(2)
C1 S1B C3 C8 3.6(6)
C1 S1B C3 C2 -4.6(11)
C8 C3 C4 C5 0.3(3)
C2 C3 C4 C5 -178.7(2)
S1B C3 C4 C5 -176.8(4)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 0.4(3)
C5 C6 C7 C8 -0.2(3)
C6 C7 C8 C3 0.1(3)
C6 C7 C8 C2B 177.3(14)
C6 C7 C8 S1 -179.88(15)
C4 C3 C8 C7 -0.2(3)
C2 C3 C8 C7 179.02(19)
S1B C3 C8 C7 176.4(5)
C4 C3 C8 C2B -178.5(8)
C2 C3 C8 C2B 0.7(8)
S1B C3 C8 C2B -1.9(9)
C4 C3 C8 S1 179.87(15)
C2 C3 C8 S1 -1.0(2)
S1B C3 C8 S1 -3.6(5)
C1 C2B C8 C7 -179.3(5)
C1 C2B C8 C3 -1.7(17)
C1 C2B C8 S1 173(4)
C1 S1 C8 C7 -178.89(16)
C1 S1 C8 C3 1.09(13)
C1 S1 C8 C2B -4(3)
C16 S2 C9 C10 0.88(14)
C16 S2 C9 C17 -176.35(13)
C17 C9 C10 C11 176.16(15)
S2 C9 C10 C11 -0.78(19)
C9 C10 C11 C12 -178.88(17)
C9 C10 C11 C16 0.2(2)
C16 C11 C12 C13 -1.2(3)
C10 C11 C12 C13 177.79(18)
C11 C12 C13 C14 1.6(3)
C12 C13 C14 C15 -1.0(3)
C13 C14 C15 C16 0.0(4)
C14 C15 C16 C11 0.3(3)
C14 C15 C16 S2 -178.93(18)
C12 C11 C16 C15 0.3(3)
C10 C11 C16 C15 -178.91(19)
C12 C11 C16 S2 179.65(13)
C10 C11 C16 S2 0.46(19)
C9 S2 C16 C15 178.6(2)
C9 S2 C16 C11 -0.75(14)
C2B C1 C17 O1 43.3(13)
C2 C1 C17 O1 -143.8(2)
S1 C1 C17 O1 40.41(16)
S1B C1 C17 O1 -144.9(4)
C2B C1 C17 C18 166.0(13)
C2 C1 C17 C18 -21.1(3)
S1 C1 C17 C18 163.04(11)
S1B C1 C17 C18 -22.3(4)
C2B C1 C17 C9 -74.8(13)
C2 C1 C17 C9 98.1(2)
S1 C1 C17 C9 -77.71(15)
S1B C1 C17 C9 96.9(4)
C10 C9 C17 O1 146.49(16)
S2 C9 C17 O1 -36.73(17)
C10 C9 C17 C18 25.1(2)
S2 C9 C17 C18 -158.09(12)
C10 C9 C17 C1 -94.43(19)
S2 C9 C17 C1 82.35(15)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.002 -0.040 0.000 363 130 ' '
2 0.015 -0.012 0.500 363 130 ' '
