#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/93/4509362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509362
loop_
_publ_author_name
'Imai, Yoshitane'
'Kinuta, Takafumi'
'Kamon, Kensaku'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Complexation Behavior of Binaphthol/Tetrafluoro-1,4-benzoquinone
 Charge-Transfer Complex
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2393
_journal_paper_doi               10.1021/cg801287p
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C28 H18 F4 O4'
_chemical_formula_weight         494.42
_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                98.1180(10)
_cell_angle_beta                 98.9650(10)
_cell_angle_gamma                102.0640(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3749(6)
_cell_length_b                   9.8402(7)
_cell_length_c                   15.2730(12)
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.37
_cell_volume                     1053.18(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω 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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9365
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0639P)²+0.4061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                4158
_reflns_number_total             4710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801287psup1.cif
_cod_data_source_block           imai810_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4509362
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
C1 C 0.11236(18) 0.26600(13) 0.71980(8) 0.0140(3) Uani 1 1 d .
C2 C 0.14513(19) 0.14804(13) 0.66938(9) 0.0159(3) Uani 1 1 d .
C3 C 0.26154(19) 0.16156(14) 0.60406(9) 0.0176(3) Uani 1 1 d .
H3 H 0.2796 0.0793 0.5691 0.021 Uiso 1 1 calc R
C4 C 0.34758(19) 0.29135(14) 0.59107(9) 0.0165(3) Uani 1 1 d .
H4 H 0.4262 0.2987 0.5474 0.020 Uiso 1 1 calc R
C5 C 0.40772(18) 0.55283(14) 0.62823(9) 0.0161(3) Uani 1 1 d .
H5 H 0.4870 0.5609 0.5849 0.019 Uiso 1 1 calc R
C6 C 0.38002(19) 0.67370(13) 0.67563(9) 0.0164(3) Uani 1 1 d .
C7 C 0.26374(19) 0.65906(14) 0.74115(9) 0.0172(3) Uani 1 1 d .
H7 H 0.2440 0.7414 0.7752 0.021 Uiso 1 1 calc R
C8 C 0.17951(18) 0.52928(13) 0.75638(9) 0.0153(3) Uani 1 1 d .
H8 H 0.1033 0.5234 0.8011 0.018 Uiso 1 1 calc R
C9 C 0.20361(18) 0.40289(13) 0.70668(8) 0.0135(3) Uani 1 1 d .
C10 C 0.32199(18) 0.41637(13) 0.64176(8) 0.0146(3) Uani 1 1 d .
O2 O 0.07093(15) 0.01364(10) 0.67761(7) 0.0216(2) Uani 1 1 d .
H2 H 0.0151 0.0143 0.7216 0.032 Uiso 1 1 calc R
C6M C 0.4712(2) 0.81887(14) 0.66176(10) 0.0225(3) Uani 1 1 d .
H6M1 H 0.5410 0.8105 0.6124 0.034 Uiso 1 1 calc R
H6M2 H 0.5585 0.8704 0.7172 0.034 Uiso 1 1 calc R
H6M3 H 0.3735 0.8702 0.6466 0.034 Uiso 1 1 calc R
C11 C -0.02073(18) 0.25024(13) 0.78424(9) 0.0139(3) Uani 1 1 d .
C12 C -0.21254(19) 0.19512(13) 0.75206(9) 0.0152(3) Uani 1 1 d .
C13 C -0.34269(18) 0.18476(13) 0.81149(9) 0.0163(3) Uani 1 1 d .
H13 H -0.4736 0.1470 0.7881 0.020 Uiso 1 1 calc R
C14 C -0.28104(19) 0.22860(13) 0.90184(9) 0.0160(3) Uani 1 1 d .
H14 H -0.3700 0.2234 0.9408 0.019 Uiso 1 1 calc R
C15 C -0.01870(19) 0.32091(13) 1.03298(9) 0.0159(3) Uani 1 1 d .
H15 H -0.1073 0.3155 1.0721 0.019 Uiso 1 1 calc R
C16 C 0.17041(19) 0.36631(13) 1.06947(9) 0.0163(3) Uani 1 1 d .
C17 C 0.29972(19) 0.37525(13) 1.00948(9) 0.0164(3) Uani 1 1 d .
H17 H 0.4312 0.4061 1.0336 0.020 Uiso 1 1 calc R
C18 C 0.24060(18) 0.34083(13) 0.91810(9) 0.0155(3) Uani 1 1 d .
H18 H 0.3311 0.3496 0.8800 0.019 Uiso 1 1 calc R
C19 C 0.04513(18) 0.29197(13) 0.87929(9) 0.0137(3) Uani 1 1 d .
C20 C -0.08581(18) 0.28194(13) 0.93883(9) 0.0144(3) Uani 1 1 d .
O12 O -0.29050(13) 0.14711(10) 0.66412(6) 0.0184(2) Uani 1 1 d .
H12 H -0.2120 0.1749 0.6323 0.028 Uiso 1 1 calc R
C16M C 0.2456(2) 0.40650(15) 1.16920(9) 0.0207(3) Uani 1 1 d .
H16A H 0.2591 0.5080 1.1883 0.031 Uiso 1 1 calc R
H16B H 0.3691 0.3840 1.1830 0.031 Uiso 1 1 calc R
H16C H 0.1577 0.3537 1.2013 0.031 Uiso 1 1 calc R
C21 C -0.06911(18) 0.35389(13) 0.50951(8) 0.0155(3) Uani 1 1 d .
C22 C -0.10796(18) 0.47488(14) 0.56672(9) 0.0155(3) Uani 1 1 d .
C23 C -0.04605(18) 0.60832(13) 0.55820(9) 0.0158(3) Uani 1 1 d .
O21 O -0.12838(14) 0.23254(9) 0.51776(6) 0.0188(2) Uani 1 1 d .
F22 F -0.21358(11) 0.44100(8) 0.62714(5) 0.01939(18) Uani 1 1 d .
F23 F -0.08575(12) 0.71444(8) 0.60945(5) 0.02136(19) Uani 1 1 d .
C31 C -0.06302(19) -0.03787(13) 0.90292(9) 0.0164(3) Uani 1 1 d .
C32 C 0.13842(19) 0.01320(13) 0.94554(9) 0.0171(3) Uani 1 1 d .
C33 C 0.19665(18) 0.04940(13) 1.03412(9) 0.0166(3) Uani 1 1 d .
O31 O -0.11563(14) -0.06738(10) 0.82177(6) 0.0204(2) Uani 1 1 d .
F32 F 0.25914(12) 0.01846(9) 0.88885(5) 0.02255(19) Uani 1 1 d .
F33 F 0.37849(11) 0.09586(8) 1.07159(6) 0.02182(19) 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'
F F 0.0171 0.0103 '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
C2 C1 C9 118.60(12) . .
C2 C1 C11 120.62(11) . .
C9 C1 C11 120.75(11) . .
O2 C2 C1 123.92(12) . .
O2 C2 C3 114.97(11) . .
C1 C2 C3 121.11(12) . .
C4 C3 C2 120.43(12) . .
C3 C4 C10 121.09(12) . .
C6 C5 C10 122.23(12) . .
C5 C6 C7 117.86(12) . .
C5 C6 C6M 122.45(12) . .
C7 C6 C6M 119.67(12) . .
C8 C7 C6 121.55(12) . .
C7 C8 C9 121.35(12) . .
C10 C9 C8 117.56(11) . .
C10 C9 C1 120.23(11) . .
C8 C9 C1 122.20(12) . .
C5 C10 C9 119.42(11) . .
C5 C10 C4 122.05(12) . .
C9 C10 C4 118.52(11) . .
C12 C11 C19 118.65(12) . .
C12 C11 C1 120.03(11) . .
C19 C11 C1 121.32(11) . .
O12 C12 C11 124.05(12) . .
O12 C12 C13 114.83(11) . .
C11 C12 C13 121.12(12) . .
C14 C13 C12 120.34(12) . .
C13 C14 C20 120.99(12) . .
C16 C15 C20 121.99(12) . .
C15 C16 C17 117.88(12) . .
C15 C16 C16M 123.09(12) . .
C17 C16 C16M 119.03(12) . .
C18 C17 C16 121.96(12) . .
C17 C18 C19 120.81(12) . .
C18 C19 C20 117.72(11) . .
C18 C19 C11 122.15(12) . .
C20 C19 C11 120.11(12) . .
C15 C20 C14 121.62(12) . .
C15 C20 C19 119.63(12) . .
C14 C20 C19 118.73(12) . .
O21 C21 C23 122.68(12) . 2_566
O21 C21 C22 122.21(12) . .
C23 C21 C22 115.11(11) 2_566 .
C23 C22 F22 121.59(11) . .
C23 C22 C21 123.17(12) . .
F22 C22 C21 115.23(11) . .
F23 C23 C22 121.82(12) . .
F23 C23 C21 116.45(11) . 2_566
C22 C23 C21 121.72(11) . 2_566
O31 C31 C32 122.32(12) . .
O31 C31 C33 122.26(12) . 2_557
C32 C31 C33 115.42(11) . 2_557
C33 C32 F32 121.99(12) . .
C33 C32 C31 122.65(12) . .
F32 C32 C31 115.34(11) . .
C32 C33 F33 122.03(12) . .
C32 C33 C31 121.91(12) . 2_557
F33 C33 C31 116.05(11) . 2_557
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3862(17) .
C1 C9 1.4307(17) .
C1 C11 1.4954(17) .
C2 O2 1.3529(15) .
C2 C3 1.4166(18) .
C3 C4 1.3584(19) .
C4 C10 1.4219(17) .
C5 C6 1.3729(18) .
C5 C10 1.4177(18) .
C6 C7 1.4193(18) .
C6 C6M 1.5053(18) .
C7 C8 1.3667(18) .
C8 C9 1.4222(17) .
C9 C10 1.4217(17) .
C11 C12 1.3871(18) .
C11 C19 1.4285(18) .
C12 O12 1.3506(16) .
C12 C13 1.4185(18) .
C13 C14 1.3607(19) .
C14 C20 1.4193(19) .
C15 C16 1.3720(19) .
C15 C20 1.4152(18) .
C16 C17 1.4201(18) .
C16 C16M 1.5031(18) .
C17 C18 1.3667(18) .
C18 C19 1.4227(18) .
C19 C20 1.4242(17) .
C21 O21 1.2142(16) .
C21 C23 1.4763(18) 2_566
C21 C22 1.4798(18) .
C22 C23 1.3288(18) .
C22 F22 1.3311(15) .
C23 F23 1.3256(14) .
C23 C21 1.4763(18) 2_566
C31 O31 1.2134(16) .
C31 C32 1.4755(19) .
C31 C33 1.4792(18) 2_557
C32 C33 1.327(2) .
C32 F32 1.3337(15) .
C33 F33 1.3287(15) .
C33 C31 1.4792(18) 2_557
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146912
