#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/41/7114156.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_7114156
loop_
_publ_author_name
'Toda, Fumio'
'Senzaki, Mami'
'Kuroda, Reiko'
_publ_section_title
;
 A new supramolecular system of racemic-bis-??-naphthol, benzoquinone and
 aromatic hydrocarbon, which shows high molecular recognition ability
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1788
_journal_paper_doi               10.1039/b203998m
_journal_year                    2002
_chemical_formula_moiety         'C20 H14 O2, 0.5(C6 H4 O2), C7H8'
_chemical_formula_sum            'C30 H24 O3'
_chemical_formula_weight         432.49
_chemical_name_common
;
Complex of bi-2-naphthol, p-benzoquinone and toluene
;
_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                98.011(2)
_cell_angle_beta                 97.747(2)
_cell_angle_gamma                115.541(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1524(9)
_cell_length_b                   10.8140(10)
_cell_length_c                   11.7724(11)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      1.79
_cell_volume                     1126.98(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7120
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1732
_reflns_number_gt                2727
_reflns_number_total             4925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b203998m.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7114156
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 0.41917(15) 0.93162(16) 0.14781(13) 0.0408(4) Uani 1 1 d .
H1A H 0.3872 0.9813 0.1200 0.061 Uiso 1 1 calc R
O2 O 0.53076(19) 0.68226(17) 0.04921(13) 0.0486(4) Uani 1 1 d .
H2A H 0.5889 0.7630 0.0479 0.073 Uiso 1 1 calc R
C1 C 0.5716(2) 0.9999(2) 0.17484(17) 0.0303(5) Uani 1 1 d .
C2 C 0.6500(2) 1.1331(2) 0.14957(19) 0.0364(5) Uani 1 1 d .
H2B H 0.5977 1.1752 0.1142 0.044 Uiso 1 1 calc R
C3 C 0.8013(3) 1.1997(2) 0.1768(2) 0.0425(6) Uani 1 1 d .
H3A H 0.8520 1.2871 0.1593 0.051 Uiso 1 1 calc R
C4 C 0.8838(2) 1.1385(2) 0.2314(2) 0.0414(6) Uani 1 1 d .
C5 C 1.0412(3) 1.2068(3) 0.2616(3) 0.0638(8) Uani 1 1 d .
H5A H 1.0934 1.2937 0.2435 0.077 Uiso 1 1 calc R
C6 C 1.1181(3) 1.1476(3) 0.3167(3) 0.0725(10) Uani 1 1 d .
H6A H 1.2221 1.1937 0.3354 0.087 Uiso 1 1 calc R
C7 C 1.0412(3) 1.0177(3) 0.3455(3) 0.0578(8) Uani 1 1 d .
H7A H 1.0946 0.9789 0.3846 0.069 Uiso 1 1 calc R
C8 C 0.8890(2) 0.9476(2) 0.3168(2) 0.0413(6) Uani 1 1 d .
H8A H 0.8397 0.8606 0.3355 0.050 Uiso 1 1 calc R
C9 C 0.8048(2) 1.0053(2) 0.25879(19) 0.0327(5) Uani 1 1 d .
C10 C 0.6453(2) 0.9346(2) 0.22765(17) 0.0279(4) Uani 1 1 d .
C11 C 0.5106(2) 0.6757(2) 0.16064(19) 0.0352(5) Uani 1 1 d .
C12 C 0.4346(3) 0.5386(2) 0.1794(2) 0.0459(6) Uani 1 1 d .
H12A H 0.4028 0.4613 0.1178 0.055 Uiso 1 1 calc R
C13 C 0.4079(3) 0.5194(3) 0.2865(2) 0.0464(6) Uani 1 1 d .
H13A H 0.3580 0.4286 0.2978 0.056 Uiso 1 1 calc R
C14 C 0.4545(2) 0.6347(3) 0.3814(2) 0.0388(5) Uani 1 1 d .
C15 C 0.4232(3) 0.6167(3) 0.4932(2) 0.0541(7) Uani 1 1 d .
H15A H 0.3715 0.5266 0.5054 0.065 Uiso 1 1 calc R
C16 C 0.4677(3) 0.7292(4) 0.5828(2) 0.0612(8) Uani 1 1 d .
H16A H 0.4454 0.7158 0.6555 0.073 Uiso 1 1 calc R
C17 C 0.5470(3) 0.8655(3) 0.5664(2) 0.0532(7) Uani 1 1 d .
H17A H 0.5778 0.9422 0.6285 0.064 Uiso 1 1 calc R
C18 C 0.5794(3) 0.8865(3) 0.45946(19) 0.0402(5) Uani 1 1 d .
H18A H 0.6330 0.9777 0.4499 0.048 Uiso 1 1 calc R
C19 C 0.5328(2) 0.7726(2) 0.36365(18) 0.0316(5) Uani 1 1 d .
C20 C 0.5609(2) 0.7917(2) 0.25011(18) 0.0284(4) Uani 1 1 d .
C31 C 0.9237(6) 0.5728(4) 0.1093(4) 0.0918(12) Uani 1 1 d .
H31A H 0.9017 0.5499 0.0276 0.110 Uiso 1 1 calc R
C32 C 0.8113(4) 0.5471(3) 0.1658(4) 0.0777(10) Uani 1 1 d .
H32A H 0.7123 0.5071 0.1250 0.093 Uiso 1 1 calc R
C33 C 0.8507(4) 0.5842(3) 0.2922(3) 0.0748(10) Uani 1 1 d .
H33A H 0.7771 0.5682 0.3356 0.090 Uiso 1 1 calc R
C34 C 1.0010(4) 0.6446(3) 0.3486(3) 0.0717(9) Uani 1 1 d .
C35 C 1.1030(5) 0.6654(4) 0.2831(6) 0.1012(14) Uani 1 1 d .
H35A H 1.2033 0.7061 0.3208 0.121 Uiso 1 1 calc R
C36 C 1.0679(7) 0.6309(5) 0.1679(6) 0.1186(19) Uani 1 1 d .
H36A H 1.1430 0.6466 0.1261 0.142 Uiso 1 1 calc R
C37 C 1.0470(8) 0.6880(5) 0.4777(4) 0.176(3) Uani 1 1 d .
H37A H 1.1538 0.7276 0.5010 0.263 Uiso 1 1 calc R
H37B H 1.0011 0.6078 0.5111 0.263 Uiso 1 1 calc R
H37C H 1.0160 0.7570 0.5050 0.263 Uiso 1 1 calc R
C42 C 0.1574(3) 1.0490(3) 0.0267(2) 0.0449(6) Uani 1 1 d .
C43 C 0.0555(3) 0.9212(3) 0.0595(2) 0.0519(7) Uani 1 1 d .
H43A H 0.0948 0.8715 0.0987 0.062 Uiso 1 1 calc R
C44 C -0.0910(3) 0.8751(3) 0.0347(2) 0.0519(7) Uani 1 1 d .
H44A H -0.1529 0.7936 0.0563 0.062 Uiso 1 1 calc R
O4 O 0.29326(17) 1.09042(18) 0.04863(15) 0.0471(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'
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
O1 C1 C10 117.67(18) .
O1 C1 C2 120.71(17) .
C10 C1 C2 121.61(18) .
C3 C2 C1 120.08(18) .
C2 C3 C4 121.1(2) .
C5 C4 C3 122.0(2) .
C5 C4 C9 119.14(19) .
C3 C4 C9 118.84(19) .
C6 C5 C4 121.0(2) .
C5 C6 C7 120.2(2) .
C8 C7 C6 120.7(2) .
C7 C8 C9 120.9(2) .
C8 C9 C4 118.12(19) .
C8 C9 C10 122.30(19) .
C4 C9 C10 119.58(18) .
C1 C10 C9 118.70(18) .
C1 C10 C20 120.97(17) .
C9 C10 C20 120.32(16) .
O2 C11 C20 123.70(19) .
O2 C11 C12 115.0(2) .
C20 C11 C12 121.3(2) .
C13 C12 C11 120.2(2) .
C12 C13 C14 121.1(2) .
C13 C14 C15 121.9(2) .
C13 C14 C19 118.9(2) .
C15 C14 C19 119.1(2) .
C16 C15 C14 120.8(3) .
C15 C16 C17 120.4(2) .
C18 C17 C16 120.3(3) .
C17 C18 C19 121.1(2) .
C18 C19 C14 118.3(2) .
C18 C19 C20 122.3(2) .
C14 C19 C20 119.5(2) .
C11 C20 C19 118.98(19) .
C11 C20 C10 119.59(18) .
C19 C20 C10 121.42(19) .
C32 C31 C36 121.9(4) .
C31 C32 C33 117.1(4) .
C34 C33 C32 118.9(3) .
C35 C34 C33 118.7(4) .
C35 C34 C37 120.5(5) .
C33 C34 C37 120.8(4) .
C36 C35 C34 122.8(4) .
C35 C36 C31 120.7(5) .
O4 C42 C43 121.3(2) .
O4 C42 C44 121.1(2) 2_575
C43 C42 C44 117.6(2) 2_575
C44 C43 C42 121.5(2) .
C43 C44 C42 120.9(2) 2_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.363(2) .
O2 C11 1.362(3) .
C1 C10 1.377(3) .
C1 C2 1.411(3) .
C2 C3 1.352(3) .
C3 C4 1.415(3) .
C4 C5 1.408(3) .
C4 C9 1.424(3) .
C5 C6 1.360(4) .
C6 C7 1.398(4) .
C7 C8 1.362(3) .
C8 C9 1.417(3) .
C9 C10 1.427(3) .
C10 C20 1.492(3) .
C11 C20 1.370(3) .
C11 C12 1.412(3) .
C12 C13 1.350(3) .
C13 C14 1.410(3) .
C14 C15 1.415(3) .
C14 C19 1.418(3) .
C15 C16 1.355(4) .
C16 C17 1.398(4) .
C17 C18 1.368(3) .
C18 C19 1.408(3) .
C19 C20 1.428(3) .
C31 C32 1.343(5) .
C31 C36 1.352(6) .
C32 C33 1.439(5) .
C33 C34 1.393(4) .
C34 C35 1.334(6) .
C34 C37 1.473(5) .
C35 C36 1.311(6) .
C42 O4 1.228(3) .
C42 C43 1.467(3) .
C42 C44 1.471(3) 2_575
C43 C44 1.323(3) .
C44 C42 1.471(3) 2_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184919
