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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/4/50/49/4504932.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_4504932
loop_
_publ_author_name
'Zeng, Qingdao'
'Wu, Dongxia'
'Liu, Caiming'
'Ma, Hongwei'
'Lu, Jun'
'Xu, Shandong'
'Li, Yan'
'Wang, Chen'
'Bai, Chunli'
_publ_section_title
;
 Crystal Engineering Based on Polymeric Hydrogen-Bonded Supramolecules by
 Self-Assembling of 4,4‘-(9-Fluorenylidene)diphenol and
 4,4‘-Cyclohexylidenebisphenol with Bipyridines
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1041
_journal_paper_doi               10.1021/cg049650v
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C35 H26 N2 O4'
_chemical_formula_weight         538.58
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 105.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.988(4)
_cell_length_b                   13.295(3)
_cell_length_c                   11.009(2)
_cell_measurement_reflns_used    12801
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.89
_cell_volume                     2671.9(10)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12801
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trunk
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0442
_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)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1952
_reflns_number_total             3065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049650vsi20050217_075539.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2672.0(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4504932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.11311(7) 0.07247(10) 0.92870(13) 0.0408(3) Uani 1 1 d .
H1A H 0.1021 0.1233 0.9786 0.049 Uiso 1 1 calc R
C2 C 0.17597(8) 0.01511(11) 0.97571(13) 0.0450(4) Uani 1 1 d .
H2A H 0.2059 0.0271 1.0567 0.054 Uiso 1 1 calc R
C3 C 0.19398(8) -0.05950(11) 0.90265(14) 0.0479(4) Uani 1 1 d .
C4 C 0.14702(9) -0.07894(12) 0.78495(14) 0.0543(4) Uani 1 1 d .
H4A H 0.1577 -0.1304 0.7356 0.065 Uiso 1 1 calc R
C5 C 0.08476(8) -0.02263(11) 0.74054(13) 0.0502(4) Uani 1 1 d .
H5A H 0.0535 -0.0374 0.6614 0.060 Uiso 1 1 calc R
C6 C 0.06675(7) 0.05591(10) 0.81010(12) 0.0381(3) Uani 1 1 d .
C7 C 0.0000 0.12197(14) 0.7500 0.0371(4) Uani 1 2 d S
C8 C 0.02028(7) 0.19572(10) 0.65740(12) 0.0405(3) Uani 1 1 d .
C9 C 0.04541(8) 0.17612(12) 0.55278(14) 0.0508(4) Uani 1 1 d .
H9A H 0.0507 0.1102 0.5285 0.061 Uiso 1 1 calc R
C10 C 0.06258(9) 0.25589(14) 0.48457(16) 0.0603(5) Uani 1 1 d .
H10A H 0.0788 0.2431 0.4137 0.072 Uiso 1 1 calc R
C11 C 0.05576(10) 0.35382(14) 0.52099(18) 0.0664(5) Uani 1 1 d .
H11A H 0.0677 0.4065 0.4748 0.080 Uiso 1 1 calc R
C12 C 0.03124(9) 0.37449(12) 0.62587(16) 0.0596(4) Uani 1 1 d .
H12A H 0.0270 0.4406 0.6506 0.072 Uiso 1 1 calc R
C13 C 0.01317(7) 0.29510(10) 0.69342(13) 0.0443(3) Uani 1 1 d .
C14 C 0.34643(10) -0.11696(16) 1.38477(16) 0.0778(6) Uani 1 1 d .
H14A H 0.3884 -0.0774 1.4068 0.093 Uiso 1 1 calc R
C15 C 0.32457(10) -0.16499(15) 1.47714(16) 0.0727(6) Uani 1 1 d .
H15A H 0.3520 -0.1574 1.5608 0.087 Uiso 1 1 calc R
C16 C 0.26262(8) -0.22485(11) 1.44998(13) 0.0482(4) Uani 1 1 d .
C17 C 0.22630(9) -0.23346(13) 1.32291(15) 0.0575(4) Uani 1 1 d .
H17A H 0.1850 -0.2741 1.2984 0.069 Uiso 1 1 calc R
C18 C 0.24967(10) -0.18374(13) 1.23260(16) 0.0620(5) Uani 1 1 d .
H18A H 0.2236 -0.1908 1.1481 0.074 Uiso 1 1 calc R
N1 N 0.30913(7) -0.12515(11) 1.26283(13) 0.0579(4) Uani 1 1 d .
O1 O 0.25586(6) -0.11614(9) 0.94046(10) 0.0680(4) Uani 1 1 d .
H1B H 0.2779 -0.1015 1.0134 0.102 Uiso 1 1 calc R
O2 O 0.33199(7) -0.07687(10) 1.17615(11) 0.0785(4) Uani 1 1 d .
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
C6 C1 C2 121.64(13) . .
C3 C2 C1 120.19(13) . .
O1 C3 C2 123.49(14) . .
O1 C3 C4 117.64(14) . .
C2 C3 C4 118.86(13) . .
C5 C4 C3 120.23(14) . .
C4 C5 C6 122.12(14) . .
C1 C6 C5 116.86(13) . .
C1 C6 C7 123.65(12) . .
C5 C6 C7 119.40(11) . .
C6 C7 C6 110.16(15) 2_556 .
C6 C7 C8 108.85(7) 2_556 2_556
C6 C7 C8 114.01(7) . 2_556
C6 C7 C8 114.01(7) 2_556 .
C6 C7 C8 108.85(7) . .
C8 C7 C8 100.78(15) 2_556 .
C9 C8 C13 119.72(13) . .
C9 C8 C7 129.54(13) . .
C13 C8 C7 110.70(12) . .
C8 C9 C10 119.40(15) . .
C11 C10 C9 120.59(16) . .
C10 C11 C12 120.62(16) . .
C11 C12 C13 119.00(15) . .
C12 C13 C8 120.66(14) . .
C12 C13 C13 130.43(9) . 2_556
C8 C13 C13 108.90(8) . 2_556
N1 C14 C15 121.72(17) . .
C14 C15 C16 121.70(16) . .
C15 C16 C17 115.08(15) . .
C15 C16 C16 122.05(17) . 7_548
C17 C16 C16 122.88(18) . 7_548
C18 C17 C16 121.64(15) . .
N1 C18 C17 121.49(15) . .
O2 N1 C18 121.83(14) . .
O2 N1 C14 119.81(14) . .
C18 N1 C14 118.36(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3767(19) .
C1 C2 1.3908(19) .
C2 C3 1.378(2) .
C3 O1 1.3608(17) .
C3 C4 1.380(2) .
C4 C5 1.371(2) .
C5 C6 1.3922(19) .
C6 C7 1.5343(17) .
C7 C6 1.5343(17) 2_556
C7 C8 1.5379(18) 2_556
C7 C8 1.5379(18) .
C8 C9 1.387(2) .
C8 C13 1.3967(19) .
C9 C10 1.389(2) .
C10 C11 1.379(2) .
C11 C12 1.386(2) .
C12 C13 1.388(2) .
C13 C13 1.465(3) 2_556
C14 N1 1.339(2) .
C14 C15 1.359(2) .
C15 C16 1.383(2) .
C16 C17 1.384(2) .
C16 C16 1.477(3) 7_548
C17 C18 1.366(2) .
C18 N1 1.336(2) .
N1 O2 1.3189(17) .
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
O1 H1B O2 0.82 1.83 2.6515(19) 175.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86042906
