#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:18:21 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516426.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_4516426
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         'C40 H26 O2 S4, 2(C3 H7 N O)'
_chemical_formula_sum            'C46 H40 N2 O4 S4'
_chemical_formula_weight         813.04
_chemical_name_systematic
;
 '1,4-Bis[di(benzo[b]thien-2-yl)hydroxymethyl]benzen dimethyl formamide disolvate'
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.9240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2921(3)
_cell_length_b                   6.46110(10)
_cell_length_c                   25.1260(6)
_cell_measurement_reflns_used    8146
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.19
_cell_volume                     1980.97(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25912
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0325
_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)+(0.0450P)²+1.2280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                2969
_reflns_number_total             3494
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            4d.cif
_cod_data_source_block           feka_65_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)/c  '
_cod_database_code               4516426
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.64651(10) 0.56536(17) 0.07460(5) 0.0181(3) Uani 1 1 d .
H1 H 0.6906 0.5684 0.0515 0.027 Uiso 1 1 calc R
S1 S 0.81641(4) 0.74617(7) 0.158857(19) 0.02234(13) Uani 1 1 d .
S2 S 0.46120(4) 0.53010(7) 0.127617(18) 0.02052(13) Uani 1 1 d .
C1 C 0.72737(14) 0.8802(3) 0.11139(7) 0.0165(4) Uani 1 1 d .
C2 C 0.76797(15) 1.0652(3) 0.09894(7) 0.0198(4) Uani 1 1 d .
H2 H 0.7303 1.1579 0.0738 0.024 Uiso 1 1 calc R
C3 C 0.87431(14) 1.1087(3) 0.12763(7) 0.0191(4) Uani 1 1 d .
C4 C 0.94027(16) 1.2823(3) 0.12467(8) 0.0263(4) Uani 1 1 d .
H4 H 0.9175 1.3916 0.1006 0.032 Uiso 1 1 calc R
C5 C 1.03899(16) 1.2943(3) 0.15704(8) 0.0282(4) Uani 1 1 d .
H5 H 1.0839 1.4132 0.1554 0.034 Uiso 1 1 calc R
C6 C 1.07361(15) 1.1341(3) 0.19212(8) 0.0259(4) Uani 1 1 d .
H6 H 1.1416 1.1459 0.2143 0.031 Uiso 1 1 calc R
C7 C 1.01080(15) 0.9585(3) 0.19520(8) 0.0238(4) Uani 1 1 d .
H7 H 1.0350 0.8485 0.2188 0.029 Uiso 1 1 calc R
C8 C 0.91082(14) 0.9472(3) 0.16274(7) 0.0186(4) Uani 1 1 d .
C9 C 0.54527(14) 0.7483(3) 0.13208(7) 0.0153(4) Uani 1 1 d .
C10 C 0.52221(14) 0.8866(3) 0.17090(7) 0.0181(4) Uani 1 1 d .
H10 H 0.5608 1.0123 0.1789 0.022 Uiso 1 1 calc R
C11 C 0.43161(14) 0.8157(3) 0.19792(7) 0.0178(4) Uani 1 1 d .
C12 C 0.38268(15) 0.9099(3) 0.23915(7) 0.0214(4) Uani 1 1 d .
H12 H 0.4087 1.0397 0.2532 0.026 Uiso 1 1 calc R
C13 C 0.29652(15) 0.8133(3) 0.25931(7) 0.0243(4) Uani 1 1 d .
H13 H 0.2632 0.8777 0.2873 0.029 Uiso 1 1 calc R
C14 C 0.25726(16) 0.6220(3) 0.23925(8) 0.0256(4) Uani 1 1 d .
H14 H 0.1975 0.5583 0.2536 0.031 Uiso 1 1 calc R
C15 C 0.30432(15) 0.5250(3) 0.19886(8) 0.0229(4) Uani 1 1 d .
H15 H 0.2785 0.3941 0.1855 0.028 Uiso 1 1 calc R
C16 C 0.39054(14) 0.6233(3) 0.17819(7) 0.0177(4) Uani 1 1 d .
C17 C 0.62214(14) 0.7714(2) 0.08956(7) 0.0157(4) Uani 1 1 d .
C18 C 0.56023(13) 0.8917(3) 0.04247(7) 0.0150(4) Uani 1 1 d .
C19 C 0.47911(14) 0.9096(3) -0.04972(7) 0.0174(4) Uani 1 1 d .
H19 H 0.4652 0.8462 -0.0840 0.021 Uiso 1 1 calc R
C20 C 0.53807(14) 0.8023(3) -0.00806(7) 0.0166(4) Uani 1 1 d .
H20 H 0.5636 0.6665 -0.0140 0.020 Uiso 1 1 calc R
N1G N 0.82135(14) 0.2206(3) 0.95054(7) 0.0285(4) Uani 1 1 d .
O1G O 0.79466(12) 0.4950(2) 1.00427(6) 0.0313(3) Uani 1 1 d .
C1G C 0.76151(16) 0.3420(3) 0.97791(8) 0.0270(4) Uani 1 1 d .
H1G H 0.6861 0.3081 0.9772 0.032 Uiso 1 1 calc R
C2G C 0.7741(2) 0.0408(4) 0.92139(10) 0.0460(6) Uani 1 1 d .
H2G1 H 0.6955 0.0338 0.9245 0.069 Uiso 1 1 calc R
H2G2 H 0.8101 -0.0851 0.9365 0.069 Uiso 1 1 calc R
H2G3 H 0.7850 0.0526 0.8835 0.069 Uiso 1 1 calc R
C3G C 0.93729(19) 0.2594(4) 0.95001(11) 0.0498(7) Uani 1 1 d .
H3G1 H 0.9561 0.3946 0.9662 0.075 Uiso 1 1 calc R
H3G2 H 0.9545 0.2585 0.9129 0.075 Uiso 1 1 calc R
H3G3 H 0.9797 0.1512 0.9705 0.075 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'
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'
N N 0.0061 0.0033 '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
C17 O1 H1 109.5 . .
C8 S1 C1 91.54(8) . .
C16 S2 C9 91.00(8) . .
C2 C1 C17 130.67(16) . .
C2 C1 S1 112.28(13) . .
C17 C1 S1 117.00(12) . .
C1 C2 C3 113.33(16) . .
C1 C2 H2 123.3 . .
C3 C2 H2 123.3 . .
C4 C3 C8 119.23(16) . .
C4 C3 C2 129.01(17) . .
C8 C3 C2 111.76(16) . .
C5 C4 C3 119.38(18) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 120.79(18) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 121.08(17) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C6 C7 C8 118.07(17) . .
C6 C7 H7 121.0 . .
C8 C7 H7 121.0 . .
C7 C8 C3 121.44(17) . .
C7 C8 S1 127.48(14) . .
C3 C8 S1 111.08(13) . .
C10 C9 C17 129.36(15) . .
C10 C9 S2 113.52(13) . .
C17 C9 S2 116.68(12) . .
C9 C10 C11 111.29(16) . .
C9 C10 H10 124.4 . .
C11 C10 H10 124.4 . .
C12 C11 C16 118.48(17) . .
C12 C11 C10 129.35(17) . .
C16 C11 C10 112.18(16) . .
C13 C12 C11 119.57(17) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 121.02(18) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C15 C14 C13 120.67(18) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 118.30(17) . .
C14 C15 H15 120.8 . .
C16 C15 H15 120.8 . .
C15 C16 C11 121.96(17) . .
C15 C16 S2 126.02(14) . .
C11 C16 S2 112.01(13) . .
O1 C17 C1 109.35(14) . .
O1 C17 C9 105.22(13) . .
C1 C17 C9 111.57(14) . .
O1 C17 C18 111.68(13) . .
C1 C17 C18 111.44(14) . .
C9 C17 C18 107.41(14) . .
C20 C18 C19 118.00(16) . 3_675
C20 C18 C17 121.09(15) . .
C19 C18 C17 120.86(15) 3_675 .
C20 C19 C18 121.43(16) . 3_675
C20 C19 H19 119.3 . .
C18 C19 H19 119.3 3_675 .
C19 C20 C18 120.57(16) . .
C19 C20 H20 119.7 . .
C18 C20 H20 119.7 . .
C1G N1G C3G 120.75(19) . .
C1G N1G C2G 121.43(19) . .
C3G N1G C2G 117.79(18) . .
O1G C1G N1G 125.92(19) . .
O1G C1G H1G 117.0 . .
N1G C1G H1G 117.0 . .
N1G C2G H2G1 109.5 . .
N1G C2G H2G2 109.5 . .
H2G1 C2G H2G2 109.5 . .
N1G C2G H2G3 109.5 . .
H2G1 C2G H2G3 109.5 . .
H2G2 C2G H2G3 109.5 . .
N1G C3G H3G1 109.5 . .
N1G C3G H3G2 109.5 . .
H3G1 C3G H3G2 109.5 . .
N1G C3G H3G3 109.5 . .
H3G1 C3G H3G3 109.5 . .
H3G2 C3G H3G3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.425(2) .
O1 H1 0.8400 .
S1 C8 1.7369(18) .
S1 C1 1.7481(17) .
S2 C16 1.7315(18) .
S2 C9 1.7437(17) .
C1 C2 1.346(2) .
C1 C17 1.516(2) .
C2 C3 1.442(2) .
C2 H2 0.9500 .
C3 C4 1.391(3) .
C3 C8 1.405(3) .
C4 C5 1.379(3) .
C4 H4 0.9500 .
C5 C6 1.392(3) .
C5 H5 0.9500 .
C6 C7 1.379(3) .
C6 H6 0.9500 .
C7 C8 1.393(3) .
C7 H7 0.9500 .
C9 C10 1.377(2) .
C9 C17 1.517(2) .
C10 C11 1.447(2) .
C10 H10 0.9500 .
C11 C12 1.399(3) .
C11 C16 1.409(2) .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 C14 1.399(3) .
C13 H13 0.9500 .
C14 C15 1.378(3) .
C14 H14 0.9500 .
C15 C16 1.389(3) .
C15 H15 0.9500 .
C17 C18 1.538(2) .
C18 C20 1.391(2) .
C18 C19 1.391(2) 3_675
C19 C20 1.385(2) .
C19 C18 1.391(2) 3_675
C19 H19 0.9500 .
C20 H20 0.9500 .
N1G C1G 1.323(3) .
N1G C3G 1.449(3) .
N1G C2G 1.456(3) .
O1G C1G 1.231(2) .
C1G H1G 0.9500 .
C2G H2G1 0.9800 .
C2G H2G2 0.9800 .
C2G H2G3 0.9800 .
C3G H3G1 0.9800 .
C3G H3G2 0.9800 .
C3G H3G3 0.9800 .
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
O1 H1 O1G 0.84 1.91 2.7243(18) 163.8 1_554
C13 H13 S1 0.95 2.96 3.829(2) 152.2 2_655
C19 H19 S2 0.95 2.86 3.5761(18) 133.1 3_665
C20 H20 O1 0.95 2.42 2.787(2) 102.4 .
C12 H12 Cg4 0.95 2.73 3.5307(18) 143.0 2_655
C2 H2 Cg6 0.95 2.79 3.5569(18) 138.3 1_564
C5 H5 Cg5 0.95 2.92 3.6605(19) 135.2 1_665
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
_geom_torsion_site_symmetry_4
C8 S1 C1 C2 0.72(14) . .
C8 S1 C1 C17 178.40(14) . .
C17 C1 C2 C3 -177.44(17) . .
S1 C1 C2 C3 -0.2(2) . .
C1 C2 C3 C4 179.60(19) . .
C1 C2 C3 C8 -0.7(2) . .
C8 C3 C4 C5 -1.3(3) . .
C2 C3 C4 C5 178.38(19) . .
C3 C4 C5 C6 0.6(3) . .
C4 C5 C6 C7 0.5(3) . .
C5 C6 C7 C8 -0.9(3) . .
C6 C7 C8 C3 0.2(3) . .
C6 C7 C8 S1 -179.81(15) . .
C4 C3 C8 C7 1.0(3) . .
C2 C3 C8 C7 -178.81(17) . .
C4 C3 C8 S1 -179.05(15) . .
C2 C3 C8 S1 1.18(19) . .
C1 S1 C8 C7 178.91(18) . .
C1 S1 C8 C3 -1.08(14) . .
C16 S2 C9 C10 0.78(14) . .
C16 S2 C9 C17 -172.26(13) . .
C17 C9 C10 C11 171.08(16) . .
S2 C9 C10 C11 -0.87(19) . .
C9 C10 C11 C12 -179.64(17) . .
C9 C10 C11 C16 0.5(2) . .
C16 C11 C12 C13 0.1(3) . .
C10 C11 C12 C13 -179.77(17) . .
C11 C12 C13 C14 0.1(3) . .
C12 C13 C14 C15 0.3(3) . .
C13 C14 C15 C16 -0.8(3) . .
C14 C15 C16 C11 1.1(3) . .
C14 C15 C16 S2 -179.95(14) . .
C12 C11 C16 C15 -0.7(3) . .
C10 C11 C16 C15 179.17(16) . .
C12 C11 C16 S2 -179.80(13) . .
C10 C11 C16 S2 0.07(19) . .
C9 S2 C16 C15 -179.53(16) . .
C9 S2 C16 C11 -0.47(13) . .
C2 C1 C17 O1 129.65(19) . .
S1 C1 C17 O1 -47.52(18) . .
C2 C1 C17 C9 -114.4(2) . .
S1 C1 C17 C9 68.45(16) . .
C2 C1 C17 C18 5.7(3) . .
S1 C1 C17 C18 -171.49(12) . .
C10 C9 C17 O1 158.49(17) . .
S2 C9 C17 O1 -29.77(17) . .
C10 C9 C17 C1 40.0(2) . .
S2 C9 C17 C1 -148.25(12) . .
C10 C9 C17 C18 -82.4(2) . .
S2 C9 C17 C18 89.35(14) . .
O1 C17 C18 C20 -2.6(2) . .
C1 C17 C18 C20 120.01(17) . .
C9 C17 C18 C20 -117.51(17) . .
O1 C17 C18 C19 174.77(15) . 3_675
C1 C17 C18 C19 -62.6(2) . 3_675
C9 C17 C18 C19 59.90(19) . 3_675
C18 C19 C20 C18 -0.4(3) 3_675 .
C19 C18 C20 C19 0.4(3) 3_675 .
C17 C18 C20 C19 177.87(16) . .
C3G N1G C1G O1G 0.8(3) . .
C2G N1G C1G O1G 178.9(2) . .
