#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/93/4509364.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_4509364
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_absolute_configuration rm
_chemical_formula_sum            'C25 H18 F2 O3'
_chemical_formula_weight         404.39
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.653(3)
_cell_length_b                   7.1965(12)
_cell_length_c                   13.694(2)
_cell_measurement_reflns_used    2152
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.49
_cell_volume                     1936.8(5)
_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      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.1397
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14660
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.752
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.752
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2152
_reflns_number_total             4844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801287psup1.cif
_cod_data_source_block           imai810_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        1936.8(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               4509364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -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 0.1750(2) 0.8546(4) 0.6973(2) 0.0522(9) Uani 1 1 d .
C2 C 0.1259(3) 0.7590(4) 0.6481(2) 0.0657(11) Uani 1 1 d .
C3 C 0.1431(3) 0.6304(5) 0.5728(2) 0.0872(15) Uani 1 1 d .
H3 H 0.1082 0.5694 0.5370 0.105 Uiso 1 1 calc R
C4 C 0.2086(3) 0.5959(5) 0.5527(3) 0.0886(17) Uani 1 1 d .
H4 H 0.2195 0.5073 0.5037 0.106 Uiso 1 1 calc R
C5 C 0.3306(3) 0.6600(6) 0.5817(3) 0.1003(19) Uani 1 1 d .
H5 H 0.3418 0.5670 0.5351 0.120 Uiso 1 1 calc R
C6 C 0.3833(2) 0.7541(6) 0.6224(3) 0.0852(15) Uani 1 1 d .
C7 C 0.3653(2) 0.8880(5) 0.6977(3) 0.0757(12) Uani 1 1 d .
H7 H 0.3998 0.9556 0.7308 0.091 Uiso 1 1 calc R
C8 C 0.2985(2) 0.9157(5) 0.7203(2) 0.0645(11) Uani 1 1 d .
H8 H 0.2880 1.0056 0.7688 0.077 Uiso 1 1 calc R
C9 C 0.2439(2) 0.8201(4) 0.6767(2) 0.0629(11) Uani 1 1 d .
C10 C 0.2613(3) 0.6860(5) 0.6014(2) 0.0713(12) Uani 1 1 d .
O2 O 0.05819(16) 0.7791(4) 0.66266(15) 0.0843(8) Uani 1 1 d .
H2 H 0.0515 0.8362 0.7153 0.126 Uiso 1 1 calc R
C6M C 0.4567(2) 0.7307(6) 0.5968(3) 0.1247(19) Uani 1 1 d .
H6M1 H 0.4613 0.6372 0.5453 0.187 Uiso 1 1 calc R
H6M2 H 0.4820 0.6903 0.6548 0.187 Uiso 1 1 calc R
H6M3 H 0.4751 0.8495 0.5738 0.187 Uiso 1 1 calc R
C11 C 0.15744(16) 1.0034(4) 0.77012(17) 0.0401(8) Uani 1 1 d .
C12 C 0.13546(18) 1.1728(4) 0.73631(19) 0.0524(9) Uani 1 1 d .
C13 C 0.12166(15) 1.3205(4) 0.79946(18) 0.0433(7) Uani 1 1 d .
H13 H 0.1077 1.4369 0.7737 0.052 Uiso 1 1 calc R
C14 C 0.12809(13) 1.2985(3) 0.89647(18) 0.0333(6) Uani 1 1 d .
H14 H 0.1182 1.3997 0.9387 0.040 Uiso 1 1 calc R
C15 C 0.15538(12) 1.1021(4) 1.03837(17) 0.0282(6) Uani 1 1 d .
H15 H 0.1462 1.2033 1.0810 0.034 Uiso 1 1 calc R
C16 C 0.17419(14) 0.9342(4) 1.07733(18) 0.0330(7) Uani 1 1 d .
C17 C 0.18884(11) 0.7869(3) 1.01261(18) 0.0324(6) Uani 1 1 d .
H17 H 0.2020 0.6699 1.0386 0.039 Uiso 1 1 calc R
C18 C 0.18473(12) 0.8075(4) 0.91483(18) 0.0322(6) Uani 1 1 d .
H18 H 0.1956 0.7057 0.8735 0.039 Uiso 1 1 calc R
C19 C 0.16441(13) 0.9785(3) 0.87281(17) 0.0302(6) Uani 1 1 d .
C20 C 0.14926(13) 1.1286(4) 0.93630(18) 0.0295(7) Uani 1 1 d .
O12 O 0.12919(18) 1.1940(3) 0.63830(13) 0.0962(10) Uani 1 1 d .
H12 H 0.1135 1.3001 0.6260 0.144 Uiso 1 1 calc R
C16M C 0.17932(15) 0.9080(4) 1.18691(19) 0.0434(7) Uani 1 1 d .
H16A H 0.1715 1.0272 1.2196 0.065 Uiso 1 1 calc R
H16B H 0.2248 0.8619 1.2036 0.065 Uiso 1 1 calc R
H16C H 0.1450 0.8179 1.2084 0.065 Uiso 1 1 calc R
C21 C 1.0000 1.0000 0.8964(3) 0.0301(9) Uani 1 2 d S
C22 C 1.01771(13) 0.8358(4) 0.95198(19) 0.0331(7) Uani 1 1 d .
C23 C 1.01704(15) 0.8351(4) 1.0476(2) 0.0427(8) Uani 1 1 d .
C24 C 1.0000 1.0000 1.1053(3) 0.0461(12) Uani 1 2 d S
O21 O 1.0000 1.0000 0.80731(18) 0.0453(8) Uani 1 2 d S
O24 O 1.0000 1.0000 1.1937(2) 0.0786(12) Uani 1 2 d S
F22 F 1.03306(8) 0.6842(2) 0.90029(13) 0.0530(5) Uani 1 1 d .
F23 F 1.03243(9) 0.6829(3) 1.09903(14) 0.0724(6) 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 119.6(3) . .
C2 C1 C11 121.6(3) . .
C9 C1 C11 118.7(3) . .
O2 C2 C1 124.7(3) . .
O2 C2 C3 114.2(4) . .
C1 C2 C3 121.1(4) . .
C4 C3 C2 119.8(5) . .
C3 C4 C10 122.0(4) . .
C6 C5 C10 126.6(4) . .
C5 C6 C7 115.8(4) . .
C5 C6 C6M 125.8(4) . .
C7 C6 C6M 118.4(5) . .
C8 C7 C6 119.5(4) . .
C7 C8 C9 124.5(4) . .
C1 C9 C8 124.2(3) . .
C1 C9 C10 119.1(4) . .
C8 C9 C10 116.6(4) . .
C4 C10 C5 124.6(4) . .
C4 C10 C9 118.4(4) . .
C5 C10 C9 117.0(4) . .
C12 C11 C19 118.3(2) . .
C12 C11 C1 118.8(2) . .
C19 C11 C1 122.9(3) . .
O12 C12 C11 117.5(2) . .
O12 C12 C13 120.6(3) . .
C11 C12 C13 121.8(2) . .
C14 C13 C12 120.3(3) . .
C13 C14 C20 121.0(3) . .
C16 C15 C20 121.7(2) . .
C15 C16 C17 118.2(2) . .
C15 C16 C16M 120.8(2) . .
C17 C16 C16M 121.0(3) . .
C18 C17 C16 121.9(3) . .
C17 C18 C19 121.1(2) . .
C18 C19 C20 118.1(2) . .
C18 C19 C11 122.5(2) . .
C20 C19 C11 119.3(2) . .
C14 C20 C15 121.8(2) . .
C14 C20 C19 119.2(2) . .
C15 C20 C19 119.0(2) . .
O21 C21 C22 121.72(17) . 2_775
O21 C21 C22 121.72(17) . .
C22 C21 C22 116.6(3) 2_775 .
C23 C22 F22 122.0(3) . .
C23 C22 C21 121.8(3) . .
F22 C22 C21 116.2(2) . .
C22 C23 F23 121.8(3) . .
C22 C23 C24 122.6(3) . .
F23 C23 C24 115.6(3) . .
O24 C24 C23 122.63(18) . 2_775
O24 C24 C23 122.63(17) . .
C23 C24 C23 114.7(3) 2_775 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.364(5) .
C1 C9 1.405(5) .
C1 C11 1.504(4) .
C2 O2 1.353(4) .
C2 C3 1.426(5) .
C3 C4 1.340(6) .
C4 C10 1.391(6) .
C5 C6 1.358(6) .
C5 C10 1.401(6) .
C6 C7 1.455(5) .
C6 C6M 1.495(5) .
C7 C8 1.364(5) .
C8 C9 1.407(5) .
C9 C10 1.452(4) .
C11 C12 1.374(4) .
C11 C19 1.424(3) .
C12 O12 1.357(3) .
C12 C13 1.397(4) .
C13 C14 1.344(4) .
C14 C20 1.403(4) .
C15 C16 1.372(4) .
C15 C20 1.416(3) .
C16 C17 1.412(3) .
C16 C16M 1.516(4) .
C17 C18 1.350(3) .
C18 C19 1.416(3) .
C19 C20 1.418(3) .
C21 O21 1.220(4) .
C21 C22 1.448(3) 2_775
C21 C22 1.448(3) .
C22 C23 1.310(3) .
C22 F22 1.335(3) .
C23 F23 1.337(3) .
C23 C24 1.464(4) .
C24 O24 1.210(5) .
C24 C23 1.464(4) 2_775
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146914
