#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058330.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_7058330
loop_
_publ_author_name
'Sharada, Durgam'
'Saha, Arijit'
'Saha, Binoy K.'
_publ_section_title
;
 Charge transfer complexes as colour changing and
 disappearing--reappearing colour materials
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7562
_journal_paper_doi               10.1039/C9NJ00823C
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C6 F4 O2, C10 H8'
_chemical_formula_sum            'C16 H8 F4 O2'
_chemical_formula_weight         308.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-09 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                106.506(16)
_cell_angle_beta                 105.114(17)
_cell_angle_gamma                107.889(18)
_cell_formula_units_Z            1
_cell_length_a                   6.6927(14)
_cell_length_b                   7.6784(14)
_cell_length_c                   7.7214(14)
_cell_measurement_reflns_used    951
_cell_measurement_temperature    262.00(2)
_cell_measurement_theta_max      28.9802
_cell_measurement_theta_min      3.2973
_cell_volume                     334.68(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      262.00(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00    7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   37.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega  -52.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -37.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491 -178.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  178.0000 -120.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0613497000
_diffrn_orient_matrix_UB_12      -0.1036263000
_diffrn_orient_matrix_UB_13      -0.0579592000
_diffrn_orient_matrix_UB_21      0.0257692000
_diffrn_orient_matrix_UB_22      -0.0201527000
_diffrn_orient_matrix_UB_23      0.0853539000
_diffrn_orient_matrix_UB_31      -0.1004276000
_diffrn_orient_matrix_UB_32      0.0058910000
_diffrn_orient_matrix_UB_33      0.0098862000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3637
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         3.304
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.043(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0762P)²+0.0986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                934
_reflns_number_total             1526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj00823c2.cif
_cod_data_source_block           NP-TF
_cod_depositor_comments
'Adding full bibliography for 7058327--7058331.cif.'
_cod_original_cell_volume        334.68(12)
_cod_database_code               7058330
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C8(H8)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.6792(3) 0.6586(3) 0.3997(2) 0.0790(6) Uani 1 1 d .
F2 F 0.7092(3) 0.9052(2) 0.2035(3) 0.0798(6) Uani 1 1 d .
O1 O 0.4712(4) 0.2615(3) 0.1904(3) 0.0816(7) Uani 1 1 d .
C4 C -0.0103(4) 0.4322(3) 0.0465(3) 0.0440(6) Uani 1 1 d .
C3 C 0.6095(4) 0.7085(3) 0.1114(4) 0.0525(6) Uani 1 1 d .
C7 C 0.2047(5) 0.8431(5) 0.2679(5) 0.0751(9) Uani 1 1 d .
H7 H 0.276365 0.979639 0.342520 0.090 Uiso 1 1 calc R
C2 C 0.5949(4) 0.5891(4) 0.2059(3) 0.0525(6) Uani 1 1 d .
C6 C 0.1851(5) 0.7104(5) 0.3597(4) 0.0747(9) Uani 1 1 d .
H6 H 0.243676 0.759136 0.495457 0.090 Uiso 1 1 calc R
C1 C 0.4844(4) 0.3702(4) 0.1031(4) 0.0530(6) Uani 1 1 d .
C5 C 0.0815(4) 0.5106(5) 0.2534(4) 0.0605(7) Uani 1 1 d .
H5 H 0.070626 0.424095 0.317201 0.073 Uiso 1 1 calc R
C8 C 0.1198(4) 0.7745(4) 0.0702(4) 0.0604(7) Uani 1 1 d .
H8 H 0.133803 0.864761 0.010596 0.073 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
C5 C4 C4 118.2(3) . 2_565
C8 C4 C4 118.9(3) 2_565 2_565
C8 C4 C5 122.9(2) 2_565 .
F2 C3 C1 116.1(2) . 2_665
C2 C3 F2 122.2(2) . .
C2 C3 C1 121.6(2) . 2_665
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C8 C7 C6 120.4(3) . .
F1 C2 C1 115.7(2) . .
C3 C2 F1 122.1(2) . .
C3 C2 C1 122.2(2) . .
C7 C6 H6 119.6 . .
C5 C6 C7 120.7(3) . .
C5 C6 H6 119.6 . .
O1 C1 C3 121.9(2) . 2_665
O1 C1 C2 121.9(3) . .
C3 C1 C2 116.2(2) 2_665 .
C4 C5 H5 119.6 . .
C6 C5 C4 120.9(3) . .
C6 C5 H5 119.6 . .
C4 C8 H8 119.5 2_565 .
C7 C8 C4 120.9(3) . 2_565
C7 C8 H8 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.328(3) .
F2 C3 1.325(3) .
O1 C1 1.210(3) .
C4 C4 1.417(4) 2_565
C4 C5 1.416(3) .
C4 C8 1.413(3) 2_565
C3 C2 1.321(4) .
C3 C1 1.469(4) 2_665
C7 H7 0.9300 .
C7 C6 1.391(5) .
C7 C8 1.355(4) .
C2 C1 1.474(4) .
C6 H6 0.9300 .
C6 C5 1.357(4) .
C5 H5 0.9300 .
C8 H8 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
F1 C2 C1 O1 0.3(3) . .
F1 C2 C1 C3 -179.98(18) . 2_665
F2 C3 C2 F1 0.0(4) . .
F2 C3 C2 C1 -179.81(19) . .
C4 C4 C5 C6 0.5(4) 2_565 .
C3 C2 C1 O1 -179.9(2) . .
C3 C2 C1 C3 -0.1(4) . 2_665
C7 C6 C5 C4 -0.3(4) . .
C6 C7 C8 C4 -0.1(4) . 2_565
C1 C3 C2 F1 179.98(19) 2_665 .
C1 C3 C2 C1 0.1(4) 2_665 .
C8 C4 C5 C6 -179.9(2) 2_565 .
C8 C7 C6 C5 0.1(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179246
