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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/4/50/81/4508190.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_4508190
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(C4 H11 N)'
_chemical_formula_sum            'C46 H48 N2 O2'
_chemical_formula_weight         660.86
_space_group_IT_number           14
_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                 90.072(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8726(9)
_cell_length_b                   13.1383(11)
_cell_length_c                   12.2294(10)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.39
_cell_volume                     1907.6(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33602
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0369
_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)+(0.0476P)²+0.6014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3756
_reflns_number_total             4385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400707s_si_008.cif
_cod_data_source_block           skob112afin
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4508190
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
O1 O 0.86458(6) 0.06860(6) 0.42540(6) 0.01884(17) Uani 1 1 d .
H1 H 0.9342 0.0752 0.4155 0.028 Uiso 1 1 calc R
C1 C 0.82962(8) 0.25000(8) 0.39387(9) 0.0173(2) Uani 1 1 d .
C2 C 0.80564(9) 0.29697(9) 0.49236(9) 0.0225(2) Uani 1 1 d .
H2 H 0.7679 0.2611 0.5489 0.027 Uiso 1 1 calc R
C3 C 0.83798(10) 0.39798(9) 0.50690(10) 0.0263(3) Uani 1 1 d .
H3 H 0.8228 0.4312 0.5743 0.032 Uiso 1 1 calc R
C4 C 0.89226(10) 0.45066(9) 0.42362(10) 0.0264(3) Uani 1 1 d .
H4 H 0.9137 0.5195 0.4348 0.032 Uiso 1 1 calc R
C5 C 0.91557(9) 0.40411(8) 0.32441(10) 0.0228(2) Uani 1 1 d .
H5 H 0.9525 0.4404 0.2676 0.027 Uiso 1 1 calc R
C6 C 0.88378(8) 0.30317(8) 0.30979(9) 0.0179(2) Uani 1 1 d .
C7 C 0.89662(8) 0.23456(8) 0.21551(9) 0.0178(2) Uani 1 1 d .
C8 C 0.94585(9) 0.24985(9) 0.11388(9) 0.0239(2) Uani 1 1 d .
H8 H 0.9794 0.3133 0.0960 0.029 Uiso 1 1 calc R
C9 C 0.94508(10) 0.17048(10) 0.03896(9) 0.0267(3) Uani 1 1 d .
H9 H 0.9787 0.1798 -0.0308 0.032 Uiso 1 1 calc R
C10 C 0.89588(9) 0.07748(9) 0.06455(9) 0.0240(2) Uani 1 1 d .
H10 H 0.8949 0.0245 0.0118 0.029 Uiso 1 1 calc R
C11 C 0.84788(9) 0.06143(8) 0.16716(9) 0.0194(2) Uani 1 1 d .
H11 H 0.8150 -0.0023 0.1853 0.023 Uiso 1 1 calc R
C12 C 0.84922(8) 0.14020(8) 0.24179(8) 0.0163(2) Uani 1 1 d .
C13 C 0.80553(8) 0.14015(8) 0.35927(8) 0.0157(2) Uani 1 1 d .
C14 C 0.68001(8) 0.11750(8) 0.36602(8) 0.0154(2) Uani 1 1 d .
C15 C 0.60590(8) 0.16536(8) 0.29401(8) 0.0171(2) Uani 1 1 d .
H15 H 0.6338 0.2107 0.2399 0.021 Uiso 1 1 calc R
C16 C 0.49156(9) 0.14659(8) 0.30165(8) 0.0187(2) Uani 1 1 d .
H16 H 0.4410 0.1784 0.2520 0.022 Uiso 1 1 calc R
C17 C 0.45018(8) 0.08149(8) 0.38163(8) 0.0167(2) Uani 1 1 d .
H17 H 0.3715 0.0692 0.3858 0.020 Uiso 1 1 calc R
C18 C 0.52217(8) 0.03387(7) 0.45593(8) 0.0134(2) Uani 1 1 d .
C19 C 0.63791(8) 0.05266(8) 0.44559(8) 0.0156(2) Uani 1 1 d .
H19 H 0.6888 0.0201 0.4944 0.019 Uiso 1 1 calc R
N1A N 0.09660(7) 0.08403(7) 0.38691(7) 0.01868(19) Uani 1 1 d .
H1A H 0.1238(12) 0.0447(11) 0.4403(12) 0.028(4) Uiso 1 1 d .
C1A C 0.12965(11) 0.22667(10) 0.51300(11) 0.0333(3) Uani 1 1 d .
H1A3 H 0.0494 0.2306 0.5313 0.050 Uiso 1 1 calc R
H1A4 H 0.1633 0.2946 0.5183 0.050 Uiso 1 1 calc R
H1A5 H 0.1676 0.1806 0.5641 0.050 Uiso 1 1 calc R
C2A C 0.14291(9) 0.18694(9) 0.39769(10) 0.0232(2) Uani 1 1 d .
H2A1 H 0.1037 0.2331 0.3462 0.028 Uiso 1 1 calc R
H2A2 H 0.2238 0.1861 0.3781 0.028 Uiso 1 1 calc R
C3A C 0.12512(9) 0.03671(9) 0.28202(9) 0.0235(2) Uani 1 1 d .
H3A1 H 0.2075 0.0406 0.2705 0.028 Uiso 1 1 calc R
H3A2 H 0.0879 0.0745 0.2220 0.028 Uiso 1 1 calc R
C4A C 0.08820(12) -0.07360(10) 0.27879(11) 0.0347(3) Uani 1 1 d .
H4A1 H 0.1251 -0.1112 0.3381 0.052 Uiso 1 1 calc R
H4A2 H 0.1093 -0.1036 0.2084 0.052 Uiso 1 1 calc R
H4A3 H 0.0063 -0.0774 0.2878 0.052 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'
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 120.80(10) .
C2 C1 C13 128.51(9) .
C6 C1 C13 110.68(9) .
C1 C2 C3 118.63(10) .
C1 C2 H2 120.7 .
C3 C2 H2 120.7 .
C4 C3 C2 120.58(11) .
C4 C3 H3 119.7 .
C2 C3 H3 119.7 .
C5 C4 C3 120.96(11) .
C5 C4 H4 119.5 .
C3 C4 H4 119.5 .
C4 C5 C6 118.60(10) .
C4 C5 H5 120.7 .
C6 C5 H5 120.7 .
C5 C6 C1 120.42(10) .
C5 C6 C7 131.04(10) .
C1 C6 C7 108.53(9) .
C8 C7 C12 120.24(10) .
C8 C7 C6 131.05(10) .
C12 C7 C6 108.71(9) .
C9 C8 C7 118.66(10) .
C9 C8 H8 120.7 .
C7 C8 H8 120.7 .
C8 C9 C10 120.93(10) .
C8 C9 H9 119.5 .
C10 C9 H9 119.5 .
C9 C10 C11 120.52(11) .
C9 C10 H10 119.7 .
C11 C10 H10 119.7 .
C12 C11 C10 118.50(10) .
C12 C11 H11 120.8 .
C10 C11 H11 120.8 .
C11 C12 C7 121.13(10) .
C11 C12 C13 128.16(9) .
C7 C12 C13 110.70(9) .
O1 C13 C14 108.75(8) .
O1 C13 C12 111.52(8) .
C14 C13 C12 112.62(8) .
O1 C13 C1 111.95(8) .
C14 C13 C1 110.60(8) .
C12 C13 C1 101.30(8) .
C19 C14 C15 119.51(9) .
C19 C14 C13 120.79(9) .
C15 C14 C13 119.66(9) .
C16 C15 C14 119.71(9) .
C16 C15 H15 120.1 .
C14 C15 H15 120.1 .
C15 C16 C17 120.35(9) .
C15 C16 H16 119.8 .
C17 C16 H16 119.8 .
C16 C17 C18 121.18(9) .
C16 C17 H17 119.4 .
C18 C17 H17 119.4 .
C17 C18 C19 117.52(9) .
C17 C18 C18 121.40(11) 3_656
C19 C18 C18 121.07(11) 3_656
C14 C19 C18 121.70(9) .
C14 C19 H19 119.1 .
C18 C19 H19 119.1 .
C3A N1A C2A 112.53(9) .
C3A N1A H1A 108.2(9) .
C2A N1A H1A 109.4(9) .
C2A C1A H1A3 109.5 .
C2A C1A H1A4 109.5 .
H1A3 C1A H1A4 109.5 .
C2A C1A H1A5 109.5 .
H1A3 C1A H1A5 109.5 .
H1A4 C1A H1A5 109.5 .
N1A C2A C1A 111.29(10) .
N1A C2A H2A1 109.4 .
C1A C2A H2A1 109.4 .
N1A C2A H2A2 109.4 .
C1A C2A H2A2 109.4 .
H2A1 C2A H2A2 108.0 .
N1A C3A C4A 111.20(10) .
N1A C3A H3A1 109.4 .
C4A C3A H3A1 109.4 .
N1A C3A H3A2 109.4 .
C4A C3A H3A2 109.4 .
H3A1 C3A H3A2 108.0 .
C3A C4A H4A1 109.5 .
C3A C4A H4A2 109.5 .
H4A1 C4A H4A2 109.5 .
C3A C4A H4A3 109.5 .
H4A1 C4A H4A3 109.5 .
H4A2 C4A H4A3 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 1.4240(12) .
O1 H1 0.8400 .
C1 C2 1.3833(15) .
C1 C6 1.4002(14) .
C1 C13 1.5308(14) .
C2 C3 1.3929(17) .
C2 H2 0.9500 .
C3 C4 1.3904(18) .
C3 H3 0.9500 .
C4 C5 1.3869(17) .
C4 H4 0.9500 .
C5 C6 1.3902(15) .
C5 H5 0.9500 .
C6 C7 1.4716(15) .
C7 C8 1.3887(15) .
C7 C12 1.3991(14) .
C8 C9 1.3882(17) .
C8 H8 0.9500 .
C9 C10 1.3901(17) .
C9 H9 0.9500 .
C10 C11 1.3949(15) .
C10 H10 0.9500 .
C11 C12 1.3799(15) .
C11 H11 0.9500 .
C12 C13 1.5281(14) .
C13 C14 1.5220(13) .
C14 C19 1.3870(14) .
C14 C15 1.3940(14) .
C15 C16 1.3831(14) .
C15 H15 0.9500 .
C16 C17 1.3895(14) .
C16 H16 0.9500 .
C17 C18 1.3948(14) .
C17 H17 0.9500 .
C18 C19 1.4021(13) .
C18 C18 1.4941(19) 3_656
C19 H19 0.9500 .
N1A C3A 1.4655(14) .
N1A C2A 1.4655(14) .
N1A H1A 0.893(15) .
C1A C2A 1.5120(17) .
C1A H1A3 0.9800 .
C1A H1A4 0.9800 .
C1A H1A5 0.9800 .
C2A H2A1 0.9900 .
C2A H2A2 0.9900 .
C3A C4A 1.5146(17) .
C3A H3A1 0.9900 .
C3A H3A2 0.9900 .
C4A H4A1 0.9800 .
C4A H4A2 0.9800 .
C4A H4A3 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146614
