#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052695.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_7052695
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(C4 H9 N O)'
_chemical_formula_sum            'C40 H40 N2 O4'
_chemical_formula_weight         612.74
_chemical_melting_point          264.5(5)
_chemical_name_systematic
;
1,4-bis(9-hydroxyfluoren-9-yl)benzene. morpholine clathrate
;
_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                101.6810(10)
_cell_angle_beta                 91.685(2)
_cell_angle_gamma                114.011(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9644(3)
_cell_length_b                   9.5296(3)
_cell_length_c                   10.7651(4)
_cell_measurement_reflns_used    2429
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     816.21(5)
_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 0.992
_diffrn_measured_fraction_theta_max 0.977
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6823
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Clear plates'
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       none
_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     216
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0424
_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)+(0.0536P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2427
_reflns_number_total             3669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20241c.txt
_cod_data_source_block           hmor
_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_database_code               7052695
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22854(10) 0.11905(10) 0.05075(8) 0.0218(2) Uani 1 1 d D . .
H1O H 0.1746(18) 0.0366(15) 0.0943(14) 0.050(5) Uiso 1 1 d D . .
C1 C 0.15494(16) 0.35232(15) 0.26858(13) 0.0249(3) Uani 1 1 d . . .
H1 H 0.0991 0.3564 0.1939 0.030 Uiso 1 1 calc R . .
C2 C 0.11172(17) 0.39554(16) 0.38882(14) 0.0302(3) Uani 1 1 d . . .
H2 H 0.0269 0.4312 0.3964 0.036 Uiso 1 1 calc R . .
C3 C 0.19138(18) 0.38699(16) 0.49754(14) 0.0312(3) Uani 1 1 d . . .
H3 H 0.1603 0.4165 0.5789 0.037 Uiso 1 1 calc R . .
C4 C 0.31587(17) 0.33580(16) 0.48886(13) 0.0271(3) Uani 1 1 d . . .
H4 H 0.3699 0.3296 0.5634 0.033 Uiso 1 1 calc R . .
C5 C 0.59056(17) 0.19931(16) 0.40146(13) 0.0282(3) Uani 1 1 d . . .
H5 H 0.5928 0.2148 0.4916 0.034 Uiso 1 1 calc R . .
C6 C 0.69304(18) 0.14091(17) 0.33806(14) 0.0316(4) Uani 1 1 d . . .
H6 H 0.7651 0.1147 0.3854 0.038 Uiso 1 1 calc R . .
C7 C 0.69241(17) 0.12000(16) 0.20655(13) 0.0288(3) Uani 1 1 d . . .
H7 H 0.7642 0.0804 0.1650 0.035 Uiso 1 1 calc R . .
C8 C 0.58716(16) 0.15670(15) 0.13530(13) 0.0232(3) Uani 1 1 d . . .
H8 H 0.5875 0.1441 0.0455 0.028 Uiso 1 1 calc R . .
C9 C 0.35074(15) 0.25282(15) 0.14031(11) 0.0192(3) Uani 1 1 d . . .
C10 C 0.42572(14) 0.38195(15) 0.06766(11) 0.0184(3) Uani 1 1 d . . .
C11 C 0.43857(15) 0.34214(15) -0.06211(12) 0.0212(3) Uani 1 1 d . . .
H11 H 0.3970 0.2340 -0.1058 0.025 Uiso 1 1 calc R . .
C12 C 0.48843(15) 0.54119(15) 0.12843(12) 0.0214(3) Uani 1 1 d . . .
H12 H 0.4813 0.5709 0.2170 0.026 Uiso 1 1 calc R . .
C1A C 0.28041(15) 0.30346(15) 0.25982(12) 0.0196(3) Uani 1 1 d . . .
C4A C 0.36016(15) 0.29386(15) 0.36932(12) 0.0206(3) Uani 1 1 d . . .
C5A C 0.48434(15) 0.23483(15) 0.33034(12) 0.0207(3) Uani 1 1 d . . .
C8A C 0.48197(15) 0.21190(14) 0.19765(12) 0.0192(3) Uani 1 1 d . . .
O1G O 0.13228(12) -0.24945(12) 0.32550(9) 0.0355(3) Uani 1 1 d . . .
N1G N 0.02067(14) -0.13784(13) 0.13293(11) 0.0257(3) Uani 1 1 d D . .
H1G H -0.0659(16) -0.1512(19) 0.0705(13) 0.048(5) Uiso 1 1 d D . .
C1G C 0.09744(18) -0.11494(17) 0.35754(13) 0.0303(3) Uani 1 1 d . . .
H1GA H 0.1995 -0.0184 0.3621 0.036 Uiso 1 1 calc R . .
H1GB H 0.0589 -0.1082 0.4429 0.036 Uiso 1 1 calc R . .
C2G C -0.03202(17) -0.12252(17) 0.26070(13) 0.0288(3) Uani 1 1 d . . .
H2GB H -0.1370 -0.2141 0.2608 0.035 Uiso 1 1 calc R . .
H2GA H -0.0505 -0.0254 0.2838 0.035 Uiso 1 1 calc R . .
C3G C 0.05790(19) -0.27618(17) 0.10123(14) 0.0348(4) Uani 1 1 d . . .
H3GB H 0.0983 -0.2836 0.0166 0.042 Uiso 1 1 calc R . .
H3GA H -0.0430 -0.3736 0.0972 0.042 Uiso 1 1 calc R . .
C4G C 0.1873(2) -0.26024(19) 0.20228(15) 0.0389(4) Uani 1 1 d . . .
H4GA H 0.2137 -0.3529 0.1810 0.047 Uiso 1 1 calc R . .
H4GB H 0.2890 -0.1645 0.2038 0.047 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 108.9(10) . . ?
C1A C1 C2 118.78(12) . . ?
C1A C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.57(13) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.76(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C4A 118.82(13) . . ?
C3 C4 H4 120.6 . . ?
C4A C4 H4 120.6 . . ?
C6 C5 C5A 118.57(13) . . ?
C6 C5 H5 120.7 . . ?
C5A C5 H5 120.7 . . ?
C5 C6 C7 121.19(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 120.34(13) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C8A C8 C7 118.77(12) . . ?
C8A C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O1 C9 C10 106.51(9) . . ?
O1 C9 C1A 112.19(9) . . ?
C10 C9 C1A 113.73(11) . . ?
O1 C9 C8A 111.74(10) . . ?
C10 C9 C8A 111.48(10) . . ?
C1A C9 C8A 101.31(9) . . ?
C12 C10 C11 118.03(11) . . ?
C12 C10 C9 121.75(11) . . ?
C11 C10 C9 120.18(11) . . ?
C12 C11 C10 120.73(12) 2_665 . ?
C12 C11 H11 119.6 2_665 . ?
C10 C11 H11 119.6 . . ?
C10 C12 C11 121.24(12) . 2_665 ?
C10 C12 H12 119.4 . . ?
C11 C12 H12 119.4 2_665 . ?
C1 C1A C4A 120.68(12) . . ?
C1 C1A C9 128.42(11) . . ?
C4A C1A C9 110.90(11) . . ?
C4 C4A C1A 120.36(12) . . ?
C4 C4A C5A 131.13(12) . . ?
C1A C4A C5A 108.50(11) . . ?
C5 C5A C8A 120.32(13) . . ?
C5 C5A C4A 131.05(12) . . ?
C8A C5A C4A 108.61(11) . . ?
C8 C8A C5A 120.78(12) . . ?
C8 C8A C9 128.55(11) . . ?
C5A C8A C9 110.66(11) . . ?
C1G O1G C4G 109.60(10) . . ?
C3G N1G C2G 109.96(11) . . ?
C3G N1G H1G 108.6(10) . . ?
C2G N1G H1G 109.8(10) . . ?
O1G C1G C2G 111.53(11) . . ?
O1G C1G H1GA 109.3 . . ?
C2G C1G H1GA 109.3 . . ?
O1G C1G H1GB 109.3 . . ?
C2G C1G H1GB 109.3 . . ?
H1GA C1G H1GB 108.0 . . ?
N1G C2G C1G 110.07(11) . . ?
N1G C2G H2GB 109.6 . . ?
C1G C2G H2GB 109.6 . . ?
N1G C2G H2GA 109.6 . . ?
C1G C2G H2GA 109.6 . . ?
H2GB C2G H2GA 108.2 . . ?
N1G C3G C4G 109.01(12) . . ?
N1G C3G H3GB 109.9 . . ?
C4G C3G H3GB 109.9 . . ?
N1G C3G H3GA 109.9 . . ?
C4G C3G H3GA 109.9 . . ?
H3GB C3G H3GA 108.3 . . ?
O1G C4G C3G 111.14(12) . . ?
O1G C4G H4GA 109.4 . . ?
C3G C4G H4GA 109.4 . . ?
O1G C4G H4GB 109.4 . . ?
C3G C4G H4GB 109.4 . . ?
H4GA C4G H4GB 108.0 . . ?
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 1.4346(14) . ?
O1 H1O 0.962(9) . ?
C1 C1A 1.3804(18) . ?
C1 C2 1.3924(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.3871(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 C5A 1.3899(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3886(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3911(18) . ?
C7 H7 0.9500 . ?
C8 C8A 1.3835(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.5248(17) . ?
C9 C1A 1.5263(18) . ?
C9 C8A 1.5314(17) . ?
C10 C12 1.3888(18) . ?
C10 C11 1.3925(17) . ?
C11 C12 1.3896(17) 2_665 ?
C11 H11 0.9500 . ?
C12 C11 1.3896(18) 2_665 ?
C12 H12 0.9500 . ?
C1A C4A 1.3987(17) . ?
C4A C5A 1.4742(19) . ?
C5A C8A 1.3988(17) . ?
O1G C1G 1.4187(17) . ?
O1G C4G 1.4276(18) . ?
N1G C3G 1.4658(18) . ?
N1G C2G 1.4661(17) . ?
N1G H1G 0.961(9) . ?
C1G C2G 1.5063(18) . ?
C1G H1GA 0.9900 . ?
C1G H1GB 0.9900 . ?
C2G H2GB 0.9900 . ?
C2G H2GA 0.9900 . ?
C3G C4G 1.506(2) . ?
C3G H3GB 0.9900 . ?
C3G H3GA 0.9900 . ?
C4G H4GA 0.9900 . ?
C4G H4GB 0.9900 . ?
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 0.962(9) 1.813(10) 2.7403(14) 161.1(14) .
N1G H1G O1 0.961(9) 2.083(10) 3.0236(14) 165.7(14) 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 -1.1(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C4A 0.3(2) . . . . ?
C5A C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C8A -1.0(2) . . . . ?
O1 C9 C10 C12 150.43(11) . . . . ?
C1A C9 C10 C12 26.33(16) . . . . ?
C8A C9 C10 C12 -87.44(14) . . . . ?
O1 C9 C10 C11 -32.02(15) . . . . ?
C1A C9 C10 C11 -156.12(11) . . . . ?
C8A C9 C10 C11 90.11(13) . . . . ?
C12 C10 C11 C12 -0.2(2) . . . 2_665 ?
C9 C10 C11 C12 -177.86(11) . . . 2_665 ?
C11 C10 C12 C11 0.2(2) . . . 2_665 ?
C9 C10 C12 C11 177.83(11) . . . 2_665 ?
C2 C1 C1A C4A 1.51(19) . . . . ?
C2 C1 C1A C9 -179.13(12) . . . . ?
O1 C9 C1A C1 -59.79(17) . . . . ?
C10 C9 C1A C1 61.18(16) . . . . ?
C8A C9 C1A C1 -179.10(12) . . . . ?
O1 C9 C1A C4A 119.62(11) . . . . ?
C10 C9 C1A C4A -119.41(11) . . . . ?
C8A C9 C1A C4A 0.31(13) . . . . ?
C3 C4 C4A C1A 0.09(19) . . . . ?
C3 C4 C4A C5A -179.35(13) . . . . ?
C1 C1A C4A C4 -1.01(19) . . . . ?
C9 C1A C4A C4 179.52(11) . . . . ?
C1 C1A C4A C5A 178.54(11) . . . . ?
C9 C1A C4A C5A -0.92(14) . . . . ?
C6 C5 C5A C8A -0.1(2) . . . . ?
C6 C5 C5A C4A 178.32(13) . . . . ?
C4 C4A C5A C5 2.2(2) . . . . ?
C1A C4A C5A C5 -177.33(13) . . . . ?
C4 C4A C5A C8A -179.30(13) . . . . ?
C1A C4A C5A C8A 1.21(14) . . . . ?
C7 C8 C8A C5A 1.81(19) . . . . ?
C7 C8 C8A C9 -177.01(12) . . . . ?
C5 C5A C8A C8 -1.31(19) . . . . ?
C4A C5A C8A C8 179.97(11) . . . . ?
C5 C5A C8A C9 177.70(11) . . . . ?
C4A C5A C8A C9 -1.02(14) . . . . ?
O1 C9 C8A C8 59.74(16) . . . . ?
C10 C9 C8A C8 -59.32(16) . . . . ?
C1A C9 C8A C8 179.37(12) . . . . ?
O1 C9 C8A C5A -119.18(11) . . . . ?
C10 C9 C8A C5A 121.77(12) . . . . ?
C1A C9 C8A C5A 0.46(12) . . . . ?
C4G O1G C1G C2G 58.76(15) . . . . ?
C3G N1G C2G C1G 55.92(15) . . . . ?
O1G C1G C2G N1G -57.14(15) . . . . ?
C2G N1G C3G C4G -56.95(14) . . . . ?
C1G O1G C4G C3G -60.25(15) . . . . ?
N1G C3G C4G O1G 59.58(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176022
