#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052696.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_7052696
loop_
_publ_author_name
'Bourne, Susan A.'
'Corin, Kirsten'
'Cruickshank, Dyanne L.'
'Davson, Jessica'
'Nassimbeni, Luigi R.'
'Su, Hong'
'Weber, Edwin'
_publ_section_title
;
 Enclathration of bases by a fluorenyl host: structure, stability and
 selectivity
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1556
_journal_paper_doi               10.1039/c1nj20241c
_journal_volume                  35
_journal_year                    2011
_chemical_formula_moiety         'C32 H22 O2, 2(C5 H5 N)'
_chemical_formula_sum            'C42 H32 N2 O2'
_chemical_formula_weight         596.70
_chemical_melting_point          264.5(5)
_chemical_name_common
;
1,4-bis(9-hydroxyfluoren-9-yl)benzene. pyridine clathrate
;
_chemical_name_systematic
;
1,4-bis(9-hydroxyfluoren-9-yl)benzene. pyridine clathrate
;
_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                 97.838(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8538(3)
_cell_length_b                   10.4545(4)
_cell_length_c                   17.0843(8)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      3.7
_cell_volume                     1566.58(11)
_computing_cell_refinement       'Collect (Nonius, 2000)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'Collect (Nonius, 2000)'
_computing_molecular_graphics    'XSEED, graphical interface to SHELX (1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Combination of phi and omega'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5192
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         3.67
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Clear blocks'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0399
_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)+(0.0374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                1763
_reflns_number_total             2945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20241c.txt
_cod_data_source_block           hpyr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '264-265' was changed to '264.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7052696
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 0.70430(13) 0.39219(10) 0.10995(7) 0.0231(3) Uani 1 1 d D . .
H1O H 0.629(2) 0.3383(17) 0.1301(13) 0.079(8) Uiso 1 1 d D . .
C1 C 0.94286(19) 0.16678(15) 0.14149(10) 0.0247(4) Uani 1 1 d . . .
H1 H 0.9881 0.2329 0.1750 0.030 Uiso 1 1 calc R . .
C2 C 0.9842(2) 0.03936(16) 0.15608(11) 0.0286(4) Uani 1 1 d . . .
H2 H 1.0579 0.0184 0.2000 0.034 Uiso 1 1 calc R . .
C3 C 0.9184(2) -0.05724(16) 0.10687(11) 0.0308(5) Uani 1 1 d . . .
H3 H 0.9480 -0.1436 0.1173 0.037 Uiso 1 1 calc R . .
C4 C 0.81022(19) -0.02878(15) 0.04292(11) 0.0279(4) Uani 1 1 d . . .
H4 H 0.7651 -0.0950 0.0095 0.034 Uiso 1 1 calc R . .
C5 C 0.55821(19) 0.10133(17) -0.09428(11) 0.0280(4) Uani 1 1 d . . .
H5 H 0.5591 0.0116 -0.1031 0.034 Uiso 1 1 calc R . .
C6 C 0.45842(19) 0.17993(16) -0.14247(11) 0.0282(4) Uani 1 1 d . . .
H6 H 0.3904 0.1436 -0.1844 0.034 Uiso 1 1 calc R . .
C7 C 0.45752(18) 0.31110(16) -0.12981(11) 0.0263(4) Uani 1 1 d . . .
H7 H 0.3884 0.3635 -0.1630 0.032 Uiso 1 1 calc R . .
C8 C 0.55650(18) 0.36669(16) -0.06909(10) 0.0227(4) Uani 1 1 d . . .
H8 H 0.5563 0.4566 -0.0609 0.027 Uiso 1 1 calc R . .
C9 C 0.77220(17) 0.32559(14) 0.05028(10) 0.0191(4) Uani 1 1 d . . .
C10 C 0.89250(18) 0.41555(14) 0.02532(10) 0.0187(4) Uani 1 1 d . . .
C11 C 0.86096(18) 0.54555(14) 0.01610(9) 0.0201(4) Uani 1 1 d . . .
H11 H 0.7657 0.5778 0.0271 0.024 Uiso 1 1 calc R . .
C12 C 1.03319(18) 0.37148(15) 0.00887(10) 0.0211(4) Uani 1 1 d . . .
H12 H 1.0570 0.2831 0.0149 0.025 Uiso 1 1 calc R . .
C1A C 0.83509(18) 0.19520(15) 0.07757(10) 0.0196(4) Uani 1 1 d . . .
C4A C 0.76831(18) 0.09817(15) 0.02814(10) 0.0214(4) Uani 1 1 d . . .
C5A C 0.65616(18) 0.15587(15) -0.03327(10) 0.0212(4) Uani 1 1 d . . .
C8A C 0.65525(18) 0.28858(15) -0.02083(10) 0.0196(4) Uani 1 1 d . . .
N1G N 0.50563(16) 0.24377(13) 0.18434(9) 0.0282(4) Uani 1 1 d . . .
C2G C 0.3714(2) 0.27664(17) 0.20612(12) 0.0325(5) Uani 1 1 d . . .
H2G H 0.3157 0.3442 0.1784 0.039 Uiso 1 1 calc R . .
C3G C 0.3094(2) 0.21732(18) 0.26700(11) 0.0332(5) Uani 1 1 d . . .
H3G H 0.2143 0.2446 0.2811 0.040 Uiso 1 1 calc R . .
C4G C 0.3886(2) 0.11815(17) 0.30658(11) 0.0318(5) Uani 1 1 d . . .
H4G H 0.3486 0.0751 0.3482 0.038 Uiso 1 1 calc R . .
C5G C 0.5266(2) 0.08243(16) 0.28480(11) 0.0308(5) Uani 1 1 d . . .
H5G H 0.5836 0.0142 0.3110 0.037 Uiso 1 1 calc R . .
C6G C 0.5803(2) 0.14760(16) 0.22437(10) 0.0282(4) Uani 1 1 d . . .
H6G H 0.6762 0.1229 0.2102 0.034 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 H1O 110.2(13) . . ?
C1A C1 C2 118.88(16) . . ?
C1A C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.51(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.61(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 119.14(16) . . ?
C3 C4 H4 120.4 . . ?
C4A C4 H4 120.4 . . ?
C5A C5 C6 118.97(16) . . ?
C5A C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.52(16) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.83(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C8A C8 C7 118.72(16) . . ?
C8A C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O1 C9 C1A 112.89(13) . . ?
O1 C9 C10 106.03(12) . . ?
C1A C9 C10 113.45(12) . . ?
O1 C9 C8A 112.49(12) . . ?
C1A C9 C8A 101.30(12) . . ?
C10 C9 C8A 110.84(13) . . ?
C11 C10 C12 118.13(14) . . ?
C11 C10 C9 119.79(13) . . ?
C12 C10 C9 122.05(14) . . ?
C12 C11 C10 120.80(14) 3_765 . ?
C12 C11 H11 119.6 3_765 . ?
C10 C11 H11 119.6 . . ?
C11 C12 C10 121.07(14) 3_765 . ?
C11 C12 H12 119.5 3_765 . ?
C10 C12 H12 119.5 . . ?
C1 C1A C4A 120.74(15) . . ?
C1 C1A C9 128.29(15) . . ?
C4A C1A C9 110.97(14) . . ?
C4 C4A C1A 120.12(16) . . ?
C4 C4A C5A 131.10(16) . . ?
C1A C4A C5A 108.76(14) . . ?
C5 C5A C8A 120.33(16) . . ?
C5 C5A C4A 131.31(15) . . ?
C8A C5A C4A 108.33(14) . . ?
C8 C8A C5A 120.62(15) . . ?
C8 C8A C9 128.78(14) . . ?
C5A C8A C9 110.60(14) . . ?
C2G N1G C6G 116.50(16) . . ?
N1G C2G C3G 123.48(17) . . ?
N1G C2G H2G 118.3 . . ?
C3G C2G H2G 118.3 . . ?
C4G C3G C2G 118.54(17) . . ?
C4G C3G H3G 120.7 . . ?
C2G C3G H3G 120.7 . . ?
C3G C4G C5G 118.88(17) . . ?
C3G C4G H4G 120.6 . . ?
C5G C4G H4G 120.6 . . ?
C6G C5G C4G 118.62(17) . . ?
C6G C5G H5G 120.7 . . ?
C4G C5G H5G 120.7 . . ?
N1G C6G C5G 123.98(17) . . ?
N1G C6G H6G 118.0 . . ?
C5G C6G H6G 118.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.4327(18) . ?
O1 H1O 0.972(9) . ?
C1 C1A 1.381(2) . ?
C1 C2 1.395(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C5A 1.385(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 C8A 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C1A 1.521(2) . ?
C9 C10 1.525(2) . ?
C9 C8A 1.535(2) . ?
C10 C11 1.392(2) . ?
C10 C12 1.392(2) . ?
C11 C12 1.386(2) 3_765 ?
C11 H11 0.9500 . ?
C12 C11 1.386(2) 3_765 ?
C12 H12 0.9500 . ?
C1A C4A 1.398(2) . ?
C4A C5A 1.472(2) . ?
C5A C8A 1.404(2) . ?
N1G C2G 1.337(2) . ?
N1G C6G 1.339(2) . ?
C2G C3G 1.387(3) . ?
C2G H2G 0.9500 . ?
C3G C4G 1.376(2) . ?
C3G H3G 0.9500 . ?
C4G C5G 1.377(2) . ?
C4G H4G 0.9500 . ?
C5G C6G 1.375(2) . ?
C5G H5G 0.9500 . ?
C6G H6G 0.9500 . ?
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 H1O N1G 0.972(9) 1.817(10) 2.7797(17) 170(2) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C4A 0.3(3) . . . . ?
C5A C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C8A -0.6(2) . . . . ?
O1 C9 C10 C11 -41.12(19) . . . . ?
C1A C9 C10 C11 -165.57(15) . . . . ?
C8A C9 C10 C11 81.24(18) . . . . ?
O1 C9 C10 C12 140.85(15) . . . . ?
C1A C9 C10 C12 16.4(2) . . . . ?
C8A C9 C10 C12 -96.79(18) . . . . ?
C12 C10 C11 C12 0.1(3) . . . 3_765 ?
C9 C10 C11 C12 -178.02(14) . . . 3_765 ?
C11 C10 C12 C11 -0.1(3) . . . 3_765 ?
C9 C10 C12 C11 177.97(15) . . . 3_765 ?
C2 C1 C1A C4A 0.0(2) . . . . ?
C2 C1 C1A C9 179.83(15) . . . . ?
O1 C9 C1A C1 -57.6(2) . . . . ?
C10 C9 C1A C1 63.0(2) . . . . ?
C8A C9 C1A C1 -178.13(16) . . . . ?
O1 C9 C1A C4A 122.26(14) . . . . ?
C10 C9 C1A C4A -117.09(15) . . . . ?
C8A C9 C1A C4A 1.74(16) . . . . ?
C3 C4 C4A C1A 0.0(2) . . . . ?
C3 C4 C4A C5A -178.52(17) . . . . ?
C1 C1A C4A C4 -0.1(2) . . . . ?
C9 C1A C4A C4 -179.97(14) . . . . ?
C1 C1A C4A C5A 178.71(14) . . . . ?
C9 C1A C4A C5A -1.17(18) . . . . ?
C6 C5 C5A C8A -0.5(2) . . . . ?
C6 C5 C5A C4A 177.43(16) . . . . ?
C4 C4A C5A C5 0.5(3) . . . . ?
C1A C4A C5A C5 -178.11(17) . . . . ?
C4 C4A C5A C8A 178.62(17) . . . . ?
C1A C4A C5A C8A 0.01(18) . . . . ?
C7 C8 C8A C5A 0.4(2) . . . . ?
C7 C8 C8A C9 -178.81(15) . . . . ?
C5 C5A C8A C8 0.2(2) . . . . ?
C4A C5A C8A C8 -178.21(14) . . . . ?
C5 C5A C8A C9 179.51(14) . . . . ?
C4A C5A C8A C9 1.15(18) . . . . ?
O1 C9 C8A C8 56.8(2) . . . . ?
C1A C9 C8A C8 177.56(16) . . . . ?
C10 C9 C8A C8 -61.8(2) . . . . ?
O1 C9 C8A C5A -122.53(14) . . . . ?
C1A C9 C8A C5A -1.73(16) . . . . ?
C10 C9 C8A C5A 118.96(14) . . . . ?
C6G N1G C2G C3G 0.4(3) . . . . ?
N1G C2G C3G C4G -0.9(3) . . . . ?
C2G C3G C4G C5G 0.6(3) . . . . ?
C3G C4G C5G C6G 0.2(3) . . . . ?
C2G N1G C6G C5G 0.4(3) . . . . ?
C4G C5G C6G N1G -0.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176023
