#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/47/7204778.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_7204778
loop_
_publ_author_name
'Tanaka, Koichi'
'Yamamoto, Yohei'
'Caira, Mino R.'
_publ_section_title
;
 Guest-dependent photochromism of 3,3?-bis-(4-fluoro-phenyl)-3H,3?H-
 [2,2?]biindenylidene-1,1?-dione in its inclusion crystals
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              1
_journal_paper_doi               10.1039/b314140c
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C30 H18 F2 O2 . C1 H2 CL2'
_chemical_formula_sum            'C31 H20 Cl2 F2 O2'
_chemical_formula_weight         533.37
_chemical_name_common            none
_chemical_name_systematic
;
3,3'-bis-(4-fluorophenyl)-3H,3'H-[2,2']biindenylidene-1,1'-dione
dichloromethane solvate (1:1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.365(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0486(1)
_cell_length_b                   19.3364(2)
_cell_length_c                   14.4056(2)
_cell_measurement_reflns_used    49349
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     2509.47(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT 2000'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi-scans of 1.0 and 1.2 deg.'
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49349
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0429
_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)+(0.0449P)²+1.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                4005
_reflns_number_total             5746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314140c.txt
_cod_data_source_block           c:\finfil~1\cychcls
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value '-' 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_original_sg_symbol_H-M      P21/n
_cod_database_code               7204778
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59659(18) 0.36149(9) 0.61349(12) 0.0346(4) Uani 1 1 d . . .
H1 H 0.6757 0.3904 0.6005 0.042 Uiso 1 1 calc R . .
C2 C 0.6156(2) 0.29096(10) 0.62308(14) 0.0419(4) Uani 1 1 d . . .
H2 H 0.7083 0.2711 0.6148 0.050 Uiso 1 1 calc R . .
C3 C 0.4986(2) 0.24873(10) 0.64494(14) 0.0438(5) Uani 1 1 d . . .
H3 H 0.5148 0.2010 0.6532 0.053 Uiso 1 1 calc R . .
C4 C 0.35934(19) 0.27571(9) 0.65462(13) 0.0377(4) Uani 1 1 d . . .
H4 H 0.2811 0.2469 0.6694 0.045 Uiso 1 1 calc R . .
C5 C 0.33785(17) 0.34617(8) 0.64196(11) 0.0283(3) Uani 1 1 d . . .
C6 C 0.45585(17) 0.38853(8) 0.62368(11) 0.0281(3) Uani 1 1 d . . .
C7 C 0.40749(17) 0.46118(8) 0.61838(11) 0.0269(3) Uani 1 1 d . . .
C8 C 0.24312(16) 0.46073(8) 0.62843(10) 0.0251(3) Uani 1 1 d . . .
C9 C 0.19416(16) 0.38671(8) 0.64466(11) 0.0264(3) Uani 1 1 d . . .
H9 H 0.1229 0.3720 0.5920 0.032 Uiso 1 1 calc R . .
O10 O 0.48326(12) 0.51194(6) 0.60617(8) 0.0350(3) Uani 1 1 d . . .
C11 C 0.12427(17) 0.37672(8) 0.73540(11) 0.0289(4) Uani 1 1 d . . .
C12 C 0.1989(2) 0.39554(11) 0.82007(13) 0.0459(5) Uani 1 1 d . . .
H12 H 0.2948 0.4144 0.8214 0.055 Uiso 1 1 calc R . .
C13 C 0.1342(2) 0.38702(13) 0.90298(14) 0.0572(6) Uani 1 1 d . . .
H13 H 0.1849 0.3997 0.9604 0.069 Uiso 1 1 calc R . .
C14 C -0.0062(2) 0.35943(12) 0.89853(15) 0.0519(5) Uani 1 1 d . . .
C15 C -0.0826(2) 0.33933(11) 0.81728(15) 0.0483(5) Uani 1 1 d . . .
H15 H -0.1779 0.3199 0.8168 0.058 Uiso 1 1 calc R . .
C16 C -0.01621(19) 0.34821(9) 0.73515(13) 0.0370(4) Uani 1 1 d . . .
H16 H -0.0675 0.3346 0.6783 0.044 Uiso 1 1 calc R . .
F17 F -0.07250(16) 0.35243(9) 0.97925(9) 0.0822(5) Uani 1 1 d . . .
C18 C 0.0494(2) 0.70396(9) 0.59779(13) 0.0370(4) Uani 1 1 d . . .
H18 H 0.1321 0.7335 0.5995 0.044 Uiso 1 1 calc R . .
C19 C -0.0940(2) 0.73023(10) 0.58587(13) 0.0404(4) Uani 1 1 d . . .
H19 H -0.1080 0.7782 0.5786 0.049 Uiso 1 1 calc R . .
C20 C -0.21697(19) 0.68724(9) 0.58446(12) 0.0369(4) Uani 1 1 d . . .
H20 H -0.3128 0.7064 0.5768 0.044 Uiso 1 1 calc R . .
C21 C -0.20013(18) 0.61656(9) 0.59419(11) 0.0313(4) Uani 1 1 d . . .
H21 H -0.2829 0.5871 0.5935 0.038 Uiso 1 1 calc R . .
C22 C -0.05582(17) 0.59031(8) 0.60511(10) 0.0268(3) Uani 1 1 d . . .
C23 C 0.06764(17) 0.63308(8) 0.60708(11) 0.0280(3) Uani 1 1 d . . .
C24 C 0.21196(16) 0.59233(8) 0.62016(11) 0.0263(3) Uani 1 1 d . . .
H24 H 0.2693 0.5995 0.5657 0.032 Uiso 1 1 calc R . .
C25 C 0.15835(16) 0.51776(8) 0.62172(10) 0.0251(3) Uani 1 1 d . . .
C26 C -0.00872(16) 0.51746(8) 0.61220(10) 0.0259(3) Uani 1 1 d . . .
O27 O -0.08807(12) 0.46627(6) 0.60577(8) 0.0341(3) Uani 1 1 d . . .
C28 C 0.30614(17) 0.61240(8) 0.70901(12) 0.0284(3) Uani 1 1 d . . .
C29 C 0.26456(19) 0.59388(9) 0.79567(12) 0.0369(4) Uani 1 1 d . . .
H29 H 0.1756 0.5694 0.7996 0.044 Uiso 1 1 calc R . .
C30 C 0.3520(2) 0.61075(11) 0.87694(14) 0.0483(5) Uani 1 1 d . . .
H30 H 0.3237 0.5981 0.9358 0.058 Uiso 1 1 calc R . .
C31 C 0.4811(2) 0.64659(11) 0.86839(16) 0.0512(6) Uani 1 1 d . . .
C32 C 0.5247(2) 0.66693(11) 0.78491(17) 0.0520(5) Uani 1 1 d . . .
H32 H 0.6130 0.6921 0.7817 0.062 Uiso 1 1 calc R . .
C33 C 0.43626(19) 0.64979(9) 0.70501(14) 0.0405(4) Uani 1 1 d . . .
H33 H 0.4647 0.6637 0.6467 0.049 Uiso 1 1 calc R . .
F34 F 0.56909(15) 0.66240(8) 0.94796(10) 0.0827(5) Uani 1 1 d . . .
C35 C 0.7174(2) 0.49942(11) 0.79154(14) 0.0504(5) Uani 1 1 d . . .
H35A H 0.7586 0.4659 0.7499 0.061 Uiso 1 1 calc R . .
H35B H 0.6541 0.5314 0.7529 0.061 Uiso 1 1 calc R . .
Cl36 Cl 0.60921(6) 0.45560(4) 0.86708(5) 0.0707(2) Uani 1 1 d . . .
Cl37 Cl 0.86232(7) 0.54570(4) 0.85080(4) 0.06922(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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 117.76(16) . . ?
C1 C2 C3 120.68(17) . . ?
C4 C3 C2 121.31(17) . . ?
C3 C4 C5 118.39(17) . . ?
C4 C5 C6 120.22(15) . . ?
C4 C5 C9 127.79(15) . . ?
C6 C5 C9 111.99(14) . . ?
C5 C6 C1 121.55(15) . . ?
C5 C6 C7 110.02(13) . . ?
C1 C6 C7 128.43(15) . . ?
O10 C7 C6 127.41(14) . . ?
O10 C7 C8 126.27(15) . . ?
C6 C7 C8 106.31(13) . . ?
C25 C8 C7 123.42(14) . . ?
C25 C8 C9 127.66(14) . . ?
C7 C8 C9 108.90(13) . . ?
C11 C9 C5 112.48(13) . . ?
C11 C9 C8 113.75(13) . . ?
C5 C9 C8 102.64(12) . . ?
C16 C11 C12 118.55(16) . . ?
C16 C11 C9 120.33(15) . . ?
C12 C11 C9 121.12(15) . . ?
C11 C12 C13 121.07(18) . . ?
C14 C13 C12 117.93(19) . . ?
C15 C14 F17 118.47(19) . . ?
C15 C14 C13 123.01(18) . . ?
F17 C14 C13 118.5(2) . . ?
C14 C15 C16 118.25(18) . . ?
C11 C16 C15 121.17(18) . . ?
C23 C18 C19 118.35(16) . . ?
C20 C19 C18 121.43(17) . . ?
C21 C20 C19 120.71(16) . . ?
C20 C21 C22 117.68(16) . . ?
C23 C22 C21 121.88(15) . . ?
C23 C22 C26 109.96(13) . . ?
C21 C22 C26 128.12(15) . . ?
C18 C23 C22 119.95(15) . . ?
C18 C23 C24 128.10(15) . . ?
C22 C23 C24 111.95(14) . . ?
C28 C24 C23 112.27(13) . . ?
C28 C24 C25 112.56(13) . . ?
C23 C24 C25 102.79(12) . . ?
C8 C25 C26 124.48(14) . . ?
C8 C25 C24 126.79(13) . . ?
C26 C25 C24 108.73(13) . . ?
O27 C26 C22 127.28(14) . . ?
O27 C26 C25 126.05(14) . . ?
C22 C26 C25 106.52(13) . . ?
C29 C28 C33 118.40(16) . . ?
C29 C28 C24 121.00(14) . . ?
C33 C28 C24 120.60(15) . . ?
C28 C29 C30 121.20(18) . . ?
C31 C30 C29 117.70(19) . . ?
C32 C31 F34 118.8(2) . . ?
C32 C31 C30 123.07(18) . . ?
F34 C31 C30 118.1(2) . . ?
C31 C32 C33 118.34(19) . . ?
C32 C33 C28 121.27(19) . . ?
Cl37 C35 Cl36 112.53(11) . . ?
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
C1 C2 1.380(3) . ?
C1 C6 1.397(2) . ?
C2 C3 1.396(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.386(2) . ?
C5 C6 1.390(2) . ?
C5 C9 1.522(2) . ?
C6 C7 1.471(2) . ?
C7 O10 1.2193(19) . ?
C7 C8 1.508(2) . ?
C8 C25 1.342(2) . ?
C8 C9 1.523(2) . ?
C9 C11 1.517(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.359(3) . ?
C14 F17 1.364(2) . ?
C15 C16 1.387(3) . ?
C18 C23 1.386(2) . ?
C18 C19 1.389(2) . ?
C19 C20 1.388(3) . ?
C20 C21 1.381(2) . ?
C21 C22 1.396(2) . ?
C22 C23 1.388(2) . ?
C22 C26 1.473(2) . ?
C23 C24 1.522(2) . ?
C24 C28 1.520(2) . ?
C24 C25 1.522(2) . ?
C25 C26 1.505(2) . ?
C26 O27 1.2212(19) . ?
C28 C29 1.384(2) . ?
C28 C33 1.387(2) . ?
C29 C30 1.389(3) . ?
C30 C31 1.374(3) . ?
C31 C32 1.359(3) . ?
C31 F34 1.368(2) . ?
C32 C33 1.380(3) . ?
C35 Cl37 1.743(2) . ?
C35 Cl36 1.749(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195518
