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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508188.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_4508188
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, 3(C4 H8 O2)'
_chemical_formula_sum            'C50 H50 O8'
_chemical_formula_weight         778.90
_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                95.525(1)
_cell_angle_beta                 91.841(1)
_cell_angle_gamma                111.525(1)
_cell_formula_units_Z            1
_cell_length_a                   8.3229(2)
_cell_length_b                   8.4570(2)
_cell_length_c                   15.3718(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.61
_cell_volume                     999.17(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21153
_diffrn_reflns_theta_full        29.10
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0397
_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)+(0.0593P)²+0.2846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                4469
_reflns_number_total             5347
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400707s_si_006.cif
_cod_data_source_block           skob_109a_0m
_cod_database_code               4508188
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 0.84305(10) 0.93898(9) 0.36317(5) 0.01800(17) Uani 1 1 d .
H1 H 0.9013 1.0270 0.3406 0.027 Uiso 1 1 calc R
C1 C 0.83490(13) 0.73305(13) 0.23526(7) 0.0147(2) Uani 1 1 d .
C2 C 0.66966(14) 0.67469(14) 0.19446(7) 0.0186(2) Uani 1 1 d .
H2 H 0.5743 0.6765 0.2263 0.022 Uiso 1 1 calc R
C3 C 0.64593(15) 0.61335(15) 0.10584(8) 0.0221(2) Uani 1 1 d .
H3 H 0.5335 0.5749 0.0768 0.027 Uiso 1 1 calc R
C4 C 0.78487(15) 0.60761(15) 0.05914(8) 0.0232(2) Uani 1 1 d .
H4 H 0.7659 0.5638 -0.0011 0.028 Uiso 1 1 calc R
C5 C 0.95155(14) 0.66557(14) 0.10011(7) 0.0195(2) Uani 1 1 d .
H5 H 1.0465 0.6617 0.0685 0.023 Uiso 1 1 calc R
C6 C 0.97516(13) 0.72915(13) 0.18842(7) 0.0149(2) Uani 1 1 d .
C7 C 1.13355(13) 0.80351(13) 0.24777(7) 0.0148(2) Uani 1 1 d .
C8 C 1.30540(13) 0.83368(14) 0.23196(7) 0.0182(2) Uani 1 1 d .
H8 H 1.3356 0.7977 0.1765 0.022 Uiso 1 1 calc R
C9 C 1.43179(14) 0.91812(14) 0.29981(8) 0.0213(2) Uani 1 1 d .
H9 H 1.5501 0.9411 0.2903 0.026 Uiso 1 1 calc R
C10 C 1.38728(14) 0.96931(14) 0.38124(8) 0.0215(2) Uani 1 1 d .
H10 H 1.4759 1.0283 0.4263 0.026 Uiso 1 1 calc R
C11 C 1.21429(14) 0.93545(14) 0.39796(7) 0.0185(2) Uani 1 1 d .
H11 H 1.1839 0.9688 0.4539 0.022 Uiso 1 1 calc R
C12 C 1.08876(13) 0.85190(13) 0.33050(7) 0.0146(2) Uani 1 1 d .
C13 C 0.89284(13) 0.80082(13) 0.33174(7) 0.0145(2) Uani 1 1 d .
C14 C 0.81123(13) 0.65504(13) 0.38719(7) 0.0148(2) Uani 1 1 d .
C15 C 0.87984(15) 0.52860(14) 0.39230(8) 0.0212(2) Uani 1 1 d .
H15 H 0.9803 0.5348 0.3630 0.025 Uiso 1 1 calc R
C16 C 0.80106(16) 0.39341(15) 0.44038(8) 0.0245(2) Uani 1 1 d .
H16 H 0.8480 0.3072 0.4439 0.029 Uiso 1 1 calc R
C17 C 0.65449(15) 0.38365(14) 0.48315(7) 0.0200(2) Uani 1 1 d .
H17 H 0.6037 0.2920 0.5170 0.024 Uiso 1 1 calc R
C18 C 0.57976(13) 0.50614(13) 0.47744(6) 0.0142(2) Uani 1 1 d .
C19 C 0.66179(13) 0.64238(13) 0.42891(7) 0.0151(2) Uani 1 1 d .
H19 H 0.6142 0.7279 0.4245 0.018 Uiso 1 1 calc R
O1A O 0.22970(11) 0.30454(12) 0.15004(6) 0.0282(2) Uani 1 1 d .
O2A O 0.02030(11) 0.23815(11) 0.29349(5) 0.02264(18) Uani 1 1 d .
C1A C 0.29579(15) 0.28209(15) 0.23301(8) 0.0233(2) Uani 1 1 d .
H1A1 H 0.4212 0.3519 0.2418 0.028 Uiso 1 1 calc R
H1A2 H 0.2805 0.1605 0.2339 0.028 Uiso 1 1 calc R
C2A C 0.20320(15) 0.33464(15) 0.30622(8) 0.0234(2) Uani 1 1 d .
H2A1 H 0.2482 0.3151 0.3629 0.028 Uiso 1 1 calc R
H2A2 H 0.2254 0.4583 0.3081 0.028 Uiso 1 1 calc R
C3A C -0.04603(16) 0.25850(17) 0.21003(9) 0.0272(3) Uani 1 1 d .
H3A1 H -0.0317 0.3797 0.2084 0.033 Uiso 1 1 calc R
H3A2 H -0.1712 0.1877 0.2011 0.033 Uiso 1 1 calc R
C4A C 0.04813(16) 0.20542(18) 0.13785(8) 0.0293(3) Uani 1 1 d .
H4A1 H 0.0284 0.0826 0.1375 0.035 Uiso 1 1 calc R
H4A2 H 0.0021 0.2216 0.0806 0.035 Uiso 1 1 calc R
O1B O 0.65168(11) 0.15050(11) 0.00461(6) 0.0273(2) Uani 1 1 d .
C1B C 0.51407(16) 0.13898(16) 0.05987(9) 0.0288(3) Uani 1 1 d .
H1B1 H 0.5077 0.2534 0.0727 0.035 Uiso 1 1 calc R
H1B2 H 0.5379 0.1008 0.1161 0.035 Uiso 1 1 calc R
C2B C 0.65683(16) -0.01491(16) -0.01686(10) 0.0292(3) Uani 1 1 d .
H2B1 H 0.6847 -0.0576 0.0371 0.035 Uiso 1 1 calc R
H2B2 H 0.7494 -0.0072 -0.0570 0.035 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'
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
C13 O1 H1 109.5 . .
C2 C1 C6 120.63(10) . .
C2 C1 C13 128.47(9) . .
C6 C1 C13 110.85(9) . .
C1 C2 C3 118.69(10) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C2 C3 C4 120.88(10) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C3 C4 C5 120.62(10) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 118.32(10) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
C5 C6 C1 120.84(10) . .
C5 C6 C7 130.75(10) . .
C1 C6 C7 108.39(9) . .
C8 C7 C12 120.86(10) . .
C8 C7 C6 130.52(10) . .
C12 C7 C6 108.59(9) . .
C7 C8 C9 118.06(10) . .
C7 C8 H8 121.0 . .
C9 C8 H8 121.0 . .
C10 C9 C8 120.93(10) . .
C10 C9 H9 119.5 . .
C8 C9 H9 119.5 . .
C9 C10 C11 121.12(10) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C12 C11 C10 117.94(10) . .
C12 C11 H11 121.0 . .
C10 C11 H11 121.0 . .
C11 C12 C7 121.05(10) . .
C11 C12 C13 128.16(10) . .
C7 C12 C13 110.79(9) . .
O1 C13 C12 113.20(8) . .
O1 C13 C14 107.65(8) . .
C12 C13 C14 112.53(8) . .
O1 C13 C1 113.94(8) . .
C12 C13 C1 101.05(8) . .
C14 C13 C1 108.41(8) . .
C19 C14 C15 119.47(9) . .
C19 C14 C13 120.14(9) . .
C15 C14 C13 120.29(9) . .
C16 C15 C14 119.84(10) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C17 C16 C15 120.31(10) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C16 C17 C18 121.26(10) . .
C16 C17 H17 119.4 . .
C18 C17 H17 119.4 . .
C17 C18 C19 117.58(9) . .
C17 C18 C18 121.13(11) . 2_666
C19 C18 C18 121.28(11) . 2_666
C14 C19 C18 121.51(9) . .
C14 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
C1A O1A C4A 109.51(9) . .
C3A O2A C2A 110.47(9) . .
O1A C1A C2A 110.71(10) . .
O1A C1A H1A1 109.5 . .
C2A C1A H1A1 109.5 . .
O1A C1A H1A2 109.5 . .
C2A C1A H1A2 109.5 . .
H1A1 C1A H1A2 108.1 . .
O2A C2A C1A 110.43(9) . .
O2A C2A H2A1 109.6 . .
C1A C2A H2A1 109.6 . .
O2A C2A H2A2 109.6 . .
C1A C2A H2A2 109.6 . .
H2A1 C2A H2A2 108.1 . .
O2A C3A C4A 110.35(10) . .
O2A C3A H3A1 109.6 . .
C4A C3A H3A1 109.6 . .
O2A C3A H3A2 109.6 . .
C4A C3A H3A2 109.6 . .
H3A1 C3A H3A2 108.1 . .
O1A C4A C3A 110.54(11) . .
O1A C4A H4A1 109.5 . .
C3A C4A H4A1 109.5 . .
O1A C4A H4A2 109.5 . .
C3A C4A H4A2 109.5 . .
H4A1 C4A H4A2 108.1 . .
C2B O1B C1B 109.60(9) . .
O1B C1B C2B 111.02(10) . 2_655
O1B C1B H1B1 109.4 . .
C2B C1B H1B1 109.4 2_655 .
O1B C1B H1B2 109.4 . .
C2B C1B H1B2 109.4 2_655 .
H1B1 C1B H1B2 108.0 . .
O1B C2B C1B 111.19(10) . 2_655
O1B C2B H2B1 109.4 . .
C1B C2B H2B1 109.4 2_655 .
O1B C2B H2B2 109.4 . .
C1B C2B H2B2 109.4 2_655 .
H2B1 C2B H2B2 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.4247(12) .
O1 H1 0.8400 .
C1 C2 1.3839(14) .
C1 C6 1.4000(14) .
C1 C13 1.5323(14) .
C2 C3 1.3911(16) .
C2 H2 0.9500 .
C3 C4 1.3938(17) .
C3 H3 0.9500 .
C4 C5 1.3953(16) .
C4 H4 0.9500 .
C5 C6 1.3911(15) .
C5 H5 0.9500 .
C6 C7 1.4729(14) .
C7 C8 1.3915(14) .
C7 C12 1.4022(14) .
C8 C9 1.3925(16) .
C8 H8 0.9500 .
C9 C10 1.3909(17) .
C9 H9 0.9500 .
C10 C11 1.3987(16) .
C10 H10 0.9500 .
C11 C12 1.3833(15) .
C11 H11 0.9500 .
C12 C13 1.5272(14) .
C13 C14 1.5274(14) .
C14 C19 1.3916(14) .
C14 C15 1.3918(15) .
C15 C16 1.3881(15) .
C15 H15 0.9500 .
C16 C17 1.3840(15) .
C16 H16 0.9500 .
C17 C18 1.3980(14) .
C17 H17 0.9500 .
C18 C19 1.4040(14) .
C18 C18 1.4920(19) 2_666
C19 H19 0.9500 .
O1A C1A 1.4295(15) .
O1A C4A 1.4295(15) .
O2A C3A 1.4308(15) .
O2A C2A 1.4352(14) .
C1A C2A 1.5061(16) .
C1A H1A1 0.9900 .
C1A H1A2 0.9900 .
C2A H2A1 0.9900 .
C2A H2A2 0.9900 .
C3A C4A 1.5049(18) .
C3A H3A1 0.9900 .
C3A H3A2 0.9900 .
C4A H4A1 0.9900 .
C4A H4A2 0.9900 .
O1B C2B 1.4225(15) .
O1B C1B 1.4281(14) .
C1B C2B 1.5073(18) 2_655
C1B H1B1 0.9900 .
C1B H1B2 0.9900 .
C2B C1B 1.5073(18) 2_655
C2B H2B1 0.9900 .
C2B H2B2 0.9900 .
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 -0.50(15) . .
C13 C1 C2 C3 -177.97(10) . .
C1 C2 C3 C4 1.16(17) . .
C2 C3 C4 C5 -0.87(18) . .
C3 C4 C5 C6 -0.08(17) . .
C4 C5 C6 C1 0.73(16) . .
C4 C5 C6 C7 -177.70(11) . .
C2 C1 C6 C5 -0.44(15) . .
C13 C1 C6 C5 177.43(9) . .
C2 C1 C6 C7 178.30(9) . .
C13 C1 C6 C7 -3.82(11) . .
C5 C6 C7 C8 1.09(19) . .
C1 C6 C7 C8 -177.49(10) . .
C5 C6 C7 C12 178.71(11) . .
C1 C6 C7 C12 0.14(11) . .
C12 C7 C8 C9 -2.02(15) . .
C6 C7 C8 C9 175.36(10) . .
C7 C8 C9 C10 0.60(16) . .
C8 C9 C10 C11 0.95(17) . .
C9 C10 C11 C12 -1.07(16) . .
C10 C11 C12 C7 -0.35(16) . .
C10 C11 C12 C13 -179.85(10) . .
C8 C7 C12 C11 1.93(15) . .
C6 C7 C12 C11 -175.96(9) . .
C8 C7 C12 C13 -178.49(9) . .
C6 C7 C12 C13 3.61(11) . .
C11 C12 C13 O1 51.80(14) . .
C7 C12 C13 O1 -127.74(9) . .
C11 C12 C13 C14 -70.54(14) . .
C7 C12 C13 C14 109.92(10) . .
C11 C12 C13 C1 174.04(10) . .
C7 C12 C13 C1 -5.50(10) . .
C2 C1 C13 O1 -55.02(14) . .
C6 C1 C13 O1 127.32(9) . .
C2 C1 C13 C12 -176.73(10) . .
C6 C1 C13 C12 5.60(10) . .
C2 C1 C13 C14 64.81(13) . .
C6 C1 C13 C14 -112.85(9) . .
O1 C13 C14 C19 25.09(13) . .
C12 C13 C14 C19 150.51(10) . .
C1 C13 C14 C19 -98.60(11) . .
O1 C13 C14 C15 -158.60(10) . .
C12 C13 C14 C15 -33.18(14) . .
C1 C13 C14 C15 77.72(12) . .
C19 C14 C15 C16 -1.40(17) . .
C13 C14 C15 C16 -177.74(11) . .
C14 C15 C16 C17 0.09(19) . .
C15 C16 C17 C18 1.59(19) . .
C16 C17 C18 C19 -1.88(17) . .
C16 C17 C18 C18 179.09(12) . 2_666
C15 C14 C19 C18 1.07(16) . .
C13 C14 C19 C18 177.42(9) . .
C17 C18 C19 C14 0.55(15) . .
C18 C18 C19 C14 179.57(11) 2_666 .
C4A O1A C1A C2A -58.43(13) . .
C3A O2A C2A C1A -56.59(12) . .
O1A C1A C2A O2A 57.58(12) . .
C2A O2A C3A C4A 57.01(13) . .
C1A O1A C4A C3A 58.81(13) . .
O2A C3A C4A O1A -58.45(13) . .
C2B O1B C1B C2B -56.78(15) . 2_655
C1B O1B C2B C1B 56.88(15) . 2_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146612
