#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508189.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_4508189
loop_
_publ_author_name
'Skobridis, Konstantinos'
'Theodorou, Vassiliki'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Host Polymorphs and Crystalline Host--Guest Complexes of
 3,3′-Bis(9-hydroxy-9-fluorenyl)biphenyl
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3985
_journal_paper_doi               10.1021/cg400707s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C38 H26 O2, 2(C2 H6 O S)'
_chemical_formula_sum            'C42 H38 O4 S2'
_chemical_formula_weight         670.84
_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           SHELXL-97
_cell_angle_alpha                86.412(1)
_cell_angle_beta                 72.722(1)
_cell_angle_gamma                73.155(1)
_cell_formula_units_Z            1
_cell_length_a                   8.2821(2)
_cell_length_b                   8.3786(2)
_cell_length_c                   13.5450(4)
_cell_measurement_reflns_used    8156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.69
_cell_volume                     858.71(4)
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_collection       'Kappa APEX 2 (Bruker-AXS)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  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  'CCD area detector'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17009
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.8904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0358
_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)+(0.0620P)²+0.3259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                3620
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400707s_si_007.cif
_cod_data_source_block           skob_110a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' 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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4508189
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
_atom_site_refinement_flags
O1 O -0.13878(12) 0.55854(11) 0.28918(7) 0.0176(2) Uani 1 1 d .
H1 H -0.0665 0.4643 0.2708 0.026 Uiso 1 1 calc R
C1 C 0.10833(16) 0.64828(14) 0.30807(10) 0.0137(2) Uani 1 1 d .
C2 C 0.10748(17) 0.62657(15) 0.41012(10) 0.0164(3) Uani 1 1 d .
H2 H 0.0007 0.6323 0.4632 0.020 Uiso 1 1 calc R
C3 C 0.26670(18) 0.59599(16) 0.43380(11) 0.0196(3) Uani 1 1 d .
H3 H 0.2686 0.5798 0.5035 0.024 Uiso 1 1 calc R
C4 C 0.42200(17) 0.58907(16) 0.35618(11) 0.0207(3) Uani 1 1 d .
H4 H 0.5293 0.5679 0.3734 0.025 Uiso 1 1 calc R
C5 C 0.42281(17) 0.61273(16) 0.25325(11) 0.0189(3) Uani 1 1 d .
H5 H 0.5293 0.6087 0.2004 0.023 Uiso 1 1 calc R
C6 C 0.26427(16) 0.64235(15) 0.22954(10) 0.0155(3) Uani 1 1 d .
C7 C 0.22277(17) 0.67022(15) 0.13033(10) 0.0170(3) Uani 1 1 d .
C8 C 0.33012(19) 0.67844(17) 0.03044(11) 0.0230(3) Uani 1 1 d .
H8 H 0.4518 0.6684 0.0177 0.028 Uiso 1 1 calc R
C9 C 0.2543(2) 0.70178(18) -0.05038(11) 0.0269(3) Uani 1 1 d .
H9 H 0.3255 0.7078 -0.1191 0.032 Uiso 1 1 calc R
C10 C 0.0763(2) 0.71639(18) -0.03239(11) 0.0271(3) Uani 1 1 d .
H10 H 0.0280 0.7299 -0.0888 0.033 Uiso 1 1 calc R
C11 C -0.03158(19) 0.71126(17) 0.06809(11) 0.0222(3) Uani 1 1 d .
H11 H -0.1535 0.7225 0.0808 0.027 Uiso 1 1 calc R
C12 C 0.04226(17) 0.68953(15) 0.14875(10) 0.0162(3) Uani 1 1 d .
C13 C -0.04842(16) 0.68345(15) 0.26411(10) 0.0142(2) Uani 1 1 d .
C14 C -0.17956(15) 0.84993(15) 0.30955(10) 0.0140(2) Uani 1 1 d .
C15 C -0.15884(16) 1.00065(16) 0.26631(10) 0.0160(3) Uani 1 1 d .
H15 H -0.0681 1.0014 0.2040 0.019 Uiso 1 1 calc R
C16 C -0.27188(17) 1.14991(16) 0.31495(10) 0.0171(3) Uani 1 1 d .
H16 H -0.2573 1.2528 0.2859 0.020 Uiso 1 1 calc R
C17 C -0.40556(16) 1.15024(15) 0.40531(10) 0.0162(3) Uani 1 1 d .
H17 H -0.4825 1.2535 0.4369 0.019 Uiso 1 1 calc R
C18 C -0.42905(15) 1.00046(15) 0.45082(9) 0.0132(2) Uani 1 1 d .
C19 C -0.31312(16) 0.85126(15) 0.40098(10) 0.0143(2) Uani 1 1 d .
H19 H -0.3261 0.7481 0.4304 0.017 Uiso 1 1 calc R
S1A S 0.24990(5) 0.19327(4) 0.28203(3) 0.02488(12) Uani 1 1 d .
O1A O 0.11171(14) 0.26477(12) 0.22721(9) 0.0261(2) Uani 1 1 d .
C1A C 0.4211(2) 0.0435(2) 0.19283(14) 0.0328(4) Uani 1 1 d .
H1A1 H 0.3700 -0.0306 0.1667 0.049 Uiso 1 1 calc R
H1A2 H 0.5057 -0.0223 0.2279 0.049 Uiso 1 1 calc R
H1A3 H 0.4818 0.1013 0.1350 0.049 Uiso 1 1 calc R
C2A C 0.1692(2) 0.04875(19) 0.37177(12) 0.0273(3) Uani 1 1 d .
H2A1 H 0.0636 0.1093 0.4253 0.041 Uiso 1 1 calc R
H2A2 H 0.2602 -0.0113 0.4040 0.041 Uiso 1 1 calc R
H2A3 H 0.1396 -0.0311 0.3352 0.041 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'
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_3
C13 O1 H1 109.5 .
C2 C1 C6 121.12(12) .
C2 C1 C13 127.93(11) .
C6 C1 C13 110.94(11) .
C1 C2 C3 118.69(12) .
C1 C2 H2 120.7 .
C3 C2 H2 120.7 .
C4 C3 C2 120.46(12) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
C3 C4 C5 120.93(12) .
C3 C4 H4 119.5 .
C5 C4 H4 119.5 .
C6 C5 C4 118.63(12) .
C6 C5 H5 120.7 .
C4 C5 H5 120.7 .
C5 C6 C1 120.16(12) .
C5 C6 C7 131.49(12) .
C1 C6 C7 108.35(11) .
C8 C7 C12 120.49(12) .
C8 C7 C6 130.86(12) .
C12 C7 C6 108.65(11) .
C7 C8 C9 118.20(14) .
C7 C8 H8 120.9 .
C9 C8 H8 120.9 .
C10 C9 C8 121.28(14) .
C10 C9 H9 119.4 .
C8 C9 H9 119.4 .
C9 C10 C11 120.34(13) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
C12 C11 C10 118.75(13) .
C12 C11 H11 120.6 .
C10 C11 H11 120.6 .
C11 C12 C7 120.91(13) .
C11 C12 C13 128.35(12) .
C7 C12 C13 110.74(11) .
O1 C13 C12 113.29(10) .
O1 C13 C14 107.87(10) .
C12 C13 C14 113.04(10) .
O1 C13 C1 112.59(10) .
C12 C13 C1 101.23(10) .
C14 C13 C1 108.73(10) .
C15 C14 C19 119.41(11) .
C15 C14 C13 121.24(11) .
C19 C14 C13 119.12(11) .
C16 C15 C14 119.55(12) .
C16 C15 H15 120.2 .
C14 C15 H15 120.2 .
C17 C16 C15 120.72(12) .
C17 C16 H16 119.6 .
C15 C16 H16 119.6 .
C16 C17 C18 120.98(12) .
C16 C17 H17 119.5 .
C18 C17 H17 119.5 .
C19 C18 C17 117.47(11) .
C19 C18 C18 121.14(14) 2_476
C17 C18 C18 121.38(14) 2_476
C14 C19 C18 121.87(11) .
C14 C19 H19 119.1 .
C18 C19 H19 119.1 .
O1A S1A C1A 105.18(7) .
O1A S1A C2A 105.99(7) .
C1A S1A C2A 97.28(8) .
S1A C1A H1A1 109.5 .
S1A C1A H1A2 109.5 .
H1A1 C1A H1A2 109.5 .
S1A C1A H1A3 109.5 .
H1A1 C1A H1A3 109.5 .
H1A2 C1A H1A3 109.5 .
S1A C2A H2A1 109.5 .
S1A C2A H2A2 109.5 .
H2A1 C2A H2A2 109.5 .
S1A C2A H2A3 109.5 .
H2A1 C2A H2A3 109.5 .
H2A2 C2A H2A3 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.4245(15) .
O1 H1 0.8400 .
C1 C2 1.3810(18) .
C1 C6 1.3983(17) .
C1 C13 1.5305(16) .
C2 C3 1.3974(18) .
C2 H2 0.9500 .
C3 C4 1.387(2) .
C3 H3 0.9500 .
C4 C5 1.394(2) .
C4 H4 0.9500 .
C5 C6 1.3930(17) .
C5 H5 0.9500 .
C6 C7 1.4722(18) .
C7 C8 1.3910(19) .
C7 C12 1.4023(18) .
C8 C9 1.393(2) .
C8 H8 0.9500 .
C9 C10 1.390(2) .
C9 H9 0.9500 .
C10 C11 1.395(2) .
C10 H10 0.9500 .
C11 C12 1.3814(18) .
C11 H11 0.9500 .
C12 C13 1.5242(18) .
C13 C14 1.5285(16) .
C14 C15 1.3930(17) .
C14 C19 1.3922(17) .
C15 C16 1.3902(18) .
C15 H15 0.9500 .
C16 C17 1.3847(18) .
C16 H16 0.9500 .
C17 C18 1.4021(17) .
C17 H17 0.9500 .
C18 C19 1.4019(17) .
C18 C18 1.493(2) 2_476
C19 H19 0.9500 .
S1A O1A 1.5072(10) .
S1A C1A 1.7848(17) .
S1A C2A 1.7867(16) .
C1A H1A1 0.9800 .
C1A H1A2 0.9800 .
C1A H1A3 0.9800 .
C2A H2A1 0.9800 .
C2A H2A2 0.9800 .
C2A H2A3 0.9800 .
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
C6 C1 C2 C3 -0.88(18) . .
C13 C1 C2 C3 -179.75(11) . .
C1 C2 C3 C4 0.53(19) . .
C2 C3 C4 C5 0.1(2) . .
C3 C4 C5 C6 -0.48(19) . .
C4 C5 C6 C1 0.13(18) . .
C4 C5 C6 C7 -179.42(12) . .
C2 C1 C6 C5 0.56(18) . .
C13 C1 C6 C5 179.60(11) . .
C2 C1 C6 C7 -179.80(11) . .
C13 C1 C6 C7 -0.76(14) . .
C5 C6 C7 C8 -1.4(2) . .
C1 C6 C7 C8 178.98(13) . .
C5 C6 C7 C12 178.37(13) . .
C1 C6 C7 C12 -1.22(14) . .
C12 C7 C8 C9 -1.7(2) . .
C6 C7 C8 C9 178.10(13) . .
C7 C8 C9 C10 -0.1(2) . .
C8 C9 C10 C11 1.3(2) . .
C9 C10 C11 C12 -0.7(2) . .
C10 C11 C12 C7 -1.0(2) . .
C10 C11 C12 C13 178.64(12) . .
C8 C7 C12 C11 2.27(19) . .
C6 C7 C12 C11 -177.56(12) . .
C8 C7 C12 C13 -177.45(11) . .
C6 C7 C12 C13 2.72(14) . .
C11 C12 C13 O1 56.54(17) . .
C7 C12 C13 O1 -123.76(11) . .
C11 C12 C13 C14 -66.55(17) . .
C7 C12 C13 C14 113.14(12) . .
C11 C12 C13 C1 177.33(13) . .
C7 C12 C13 C1 -2.98(13) . .
C2 C1 C13 O1 -57.55(16) . .
C6 C1 C13 O1 123.50(11) . .
C2 C1 C13 C12 -178.82(12) . .
C6 C1 C13 C12 2.22(13) . .
C2 C1 C13 C14 61.92(16) . .
C6 C1 C13 C14 -117.04(11) . .
O1 C13 C14 C15 -153.60(11) . .
C12 C13 C14 C15 -27.55(16) . .
C1 C13 C14 C15 84.02(14) . .
O1 C13 C14 C19 32.02(14) . .
C12 C13 C14 C19 158.07(11) . .
C1 C13 C14 C19 -90.35(13) . .
C19 C14 C15 C16 -0.11(18) . .
C13 C14 C15 C16 -174.47(11) . .
C14 C15 C16 C17 -0.55(19) . .
C15 C16 C17 C18 0.84(19) . .
C16 C17 C18 C19 -0.44(18) . .
C16 C17 C18 C18 178.98(13) . 2_476
C15 C14 C19 C18 0.51(18) . .
C13 C14 C19 C18 174.99(11) . .
C17 C18 C19 C14 -0.23(18) . .
C18 C18 C19 C14 -179.66(13) 2_476 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146613
