#------------------------------------------------------------------------------
#$Date: 2022-11-01 10:48:20 +0200 (Tue, 01 Nov 2022) $
#$Revision: 278885 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245744.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_7245744
loop_
_publ_author_name
'Liu, Xiao-Xu'
'Shi, Pan'
'Dai, Xia-Lin'
'Huang, Yong-Liang'
'Lu, Tongbu'
'Chen, Jia-Mei'
_publ_section_title
;
 Photophysics of charge transfer cocrystals composed of fluorene and its
 heterocyclic analogues as donors and TCNQ as an acceptor
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01232D
_journal_year                    2022
_chemical_formula_moiety         'C12 H4 N4, C12 H8 O'
_chemical_formula_sum            'C24 H12 N4 O'
_chemical_formula_weight         372.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                99.642(13)
_cell_angle_beta                 97.616(11)
_cell_angle_gamma                100.727(15)
_cell_formula_units_Z            1
_cell_length_a                   6.7631(11)
_cell_length_b                   8.0049(16)
_cell_length_c                   9.0066(11)
_cell_measurement_reflns_used    2389
_cell_measurement_temperature    293.39(10)
_cell_measurement_theta_max      78.3750
_cell_measurement_theta_min      6.6930
_cell_volume                     465.52(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  88.00   0.50    0.50    --    0.00  57.00   0.00  106
  2  ω     28.00  55.00   0.50    0.50    --    0.00  57.00-120.00   54
  3  ω    -26.00  30.00   0.50    0.50    --    0.00  57.00   0.00  112
  4  ω     39.00  85.00   0.50    0.50    --    0.00  57.00  90.00   92
  5  ω    -24.00  21.00   0.50    0.50    --    0.00  57.00-120.00   90
  6  ω     20.00 134.00   0.50    4.60    --  106.20 -82.00 120.00  228
  7  ω    116.00 165.00   0.50    4.60    --  106.20  30.00 -60.00   98
  8  ω     48.00  91.00   0.50    4.60    --  106.20 -30.00 -30.00   86
  9  ω     41.00  67.00   0.50    4.60    --  106.20 -82.00 -90.00   52
 10  ω     80.00 142.00   0.50    4.60    --  106.20 -82.00-180.00  124
 11  ω     91.00 128.00   0.50    4.60    --  106.20 -82.00 -90.00   74
 12  ω     80.00 110.00   0.50    4.60    --  106.20  30.00-120.00   60
 13  ω    126.00 179.00   0.50    4.60    --  106.20  30.00-120.00  106
 14  ω     38.00  78.00   0.50    4.60    --  106.20 -82.00   0.00   80
 15  ω     76.00 112.00   0.50    4.60    --  106.20  30.00 -60.00   72
 16  ω    109.00 187.00   0.50    4.60    --  106.20  30.00 -30.00  156
 17  ω     78.00 103.00   0.50    4.60    --  106.20  30.00 -30.00   50
 18  ω     88.00 128.00   0.50    4.60    --  106.20 -82.00   0.00   80
 19  ω     76.00 189.00   0.50    4.60    --  106.20  30.00   0.00  226
 20  ω     97.00 137.00   0.50    4.60    --  106.20 -30.00 -30.00   80
 21  ω    145.00 190.00   0.50    4.60    --  106.20  30.00-150.00   90
 22  ω     78.00 104.00   0.50    4.60    --  106.20 -61.00   0.00   52
 23  ω     53.00 138.00   0.50    4.60    --  106.20 -82.00 -60.00  170
 24  ω     32.00 136.00   0.50    4.60    --  106.20 -61.00 120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0709244000
_diffrn_orient_matrix_UB_12      0.1617170000
_diffrn_orient_matrix_UB_13      -0.0395719000
_diffrn_orient_matrix_UB_21      -0.1137459000
_diffrn_orient_matrix_UB_22      -0.1069701000
_diffrn_orient_matrix_UB_23      -0.1564278000
_diffrn_orient_matrix_UB_31      -0.1932935000
_diffrn_orient_matrix_UB_32      -0.0482294000
_diffrn_orient_matrix_UB_33      0.0703658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4446
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.322
_diffrn_reflns_theta_min         5.054
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       acicular
_exptl_crystal_F_000             192
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0543
_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)+(0.0814P)²+0.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1630
_reflns_number_total             1932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01232d2.cif
_cod_data_source_block           Dibenzofuran_7-7-8-8-Tetracyanoquinodimethane
_cod_database_code               7245744
_shelx_shelxl_version_number     2016/6
_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.
;
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C3(0.5) H3(0.5) C2(0.5) H2(0.5) C1(0.5) C6(0.5) C5(0.5) H5(0.5)
 C4(0.5) H4(0.5) O1(0.5) C10(0.5) H10(0.5) C9(0.5) H9(0.5) C8(0.5) H8(0.5)
 C7(0.5) C12(0.5) C11(0.5) H11(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C3(H3), C2(H2), C5(H5), C4(H4), C10(H10), C9(H9), C8(H8),
 C11(H11)
3.b Fitted hexagon refined as free rotating group:
 C3(C2,C1,C6,C5,C4), C10(C9,C8,C7,C12,C11)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.879
_oxdiff_exptl_absorpt_empirical_full_min 0.557
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C16 C 0.4466(2) 0.86801(17) 0.36691(14) 0.0411(3) Uani 1 1 d . . . . .
C18 C 0.5194(2) 0.95131(18) 0.64390(15) 0.0443(4) Uani 1 1 d . . . . .
H18 H 0.532529 0.921081 0.739473 0.053 Uiso 1 1 calc R . . . .
C15 C 0.3947(2) 0.73946(18) 0.23837(15) 0.0449(4) Uani 1 1 d . . . . .
C17 C 0.4691(2) 0.82649(18) 0.51741(15) 0.0446(4) Uani 1 1 d . . . . .
H17 H 0.448363 0.710861 0.526866 0.053 Uiso 1 1 calc R . . . .
N1 N 0.3470(3) 0.7970(2) -0.03561(16) 0.0717(5) Uani 1 1 d . . . . .
C13 C 0.3695(2) 0.77426(19) 0.08682(16) 0.0507(4) Uani 1 1 d . . . . .
N2 N 0.3301(3) 0.41537(19) 0.25144(19) 0.0760(5) Uani 1 1 d . . . . .
C14 C 0.3593(3) 0.5595(2) 0.24667(17) 0.0531(4) Uani 1 1 d . . . . .
C3 C -0.1312(7) -0.2788(8) 0.1622(3) 0.090(3) Uani 0.5 1 d . . P A -1
H3 H -0.163798 -0.338278 0.061255 0.108 Uiso 0.5 1 calc R . P A -1
C2 C -0.0882(6) -0.0986(8) 0.1949(5) 0.082(2) Uani 0.5 1 d G . P A -1
H2 H -0.092038 -0.037419 0.115747 0.098 Uiso 0.5 1 calc R . P A -1
C1 C -0.0394(6) -0.0097(4) 0.3458(7) 0.0607(14) Uani 0.5 1 d G . P A -1
C6 C -0.0336(5) -0.1011(6) 0.4640(3) 0.0482(9) Uani 0.5 1 d G . P A -1
C5 C -0.0766(4) -0.2814(6) 0.4314(4) 0.0606(12) Uani 0.5 1 d G . P A -1
H5 H -0.072689 -0.342530 0.510527 0.073 Uiso 0.5 1 calc R . P A -1
C4 C -0.1254(7) -0.3702(4) 0.2805(6) 0.0751(18) Uani 0.5 1 d G . P A -1
H4 H -0.154124 -0.490837 0.258648 0.090 Uiso 0.5 1 calc R . P A -1
O1 O 0.0051(4) 0.1634(4) 0.3939(3) 0.0723(8) Uani 0.5 1 d . . P A -1
C10 C 0.1293(7) 0.3428(3) 0.8083(6) 0.086(2) Uani 0.5 1 d . . P A -1
H10 H 0.165737 0.447352 0.878422 0.103 Uiso 0.5 1 calc R . P A -1
C9 C 0.1065(6) 0.1868(6) 0.8591(3) 0.0710(17) Uani 0.5 1 d G . P A -1
H9 H 0.127809 0.186938 0.963297 0.085 Uiso 0.5 1 calc R . P A -1
C8 C 0.0520(5) 0.0306(3) 0.7543(5) 0.0601(14) Uani 0.5 1 d G . P A -1
H8 H 0.036791 -0.073806 0.788291 0.072 Uiso 0.5 1 calc R . P A -1
C7 C 0.0202(5) 0.0304(4) 0.5986(4) 0.0469(12) Uani 0.5 1 d G . P A -1
C12 C 0.0429(5) 0.1864(7) 0.5477(3) 0.0591(13) Uani 0.5 1 d G . P A -1
C11 C 0.0974(6) 0.3426(4) 0.6526(6) 0.077(2) Uani 0.5 1 d G . P A -1
H11 H 0.112644 0.447019 0.618536 0.092 Uiso 0.5 1 calc R . P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C18 C16 C17 117.96(12) 2_676 . ?
C15 C16 C18 121.13(12) . 2_676 ?
C15 C16 C17 120.91(13) . . ?
C17 C18 C16 120.66(12) . 2_676 ?
C16 C15 C13 122.92(13) . . ?
C16 C15 C14 121.98(12) . . ?
C14 C15 C13 115.09(12) . . ?
C18 C17 C16 121.37(13) . . ?
N1 C13 C15 178.02(16) . . ?
N2 C14 C15 179.17(16) . . ?
C2 C3 C4 120.0 . . ?
C1 C2 C3 120.0 . . ?
C2 C1 C6 120.0 . . ?
O1 C1 C2 126.4(5) . . ?
O1 C1 C6 113.6(5) . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C7 104.0(6) . . ?
C5 C6 C7 136.0(6) . . ?
C4 C5 C6 120.0 . . ?
C5 C4 C3 120.0 . . ?
C1 O1 C12 104.4(2) . . ?
C9 C10 C11 120.0 . . ?
C8 C9 C10 120.0 . . ?
C7 C8 C9 120.0 . . ?
C8 C7 C6 134.6(6) . . ?
C8 C7 C12 120.0 . . ?
C12 C7 C6 105.4(6) . . ?
O1 C12 C7 112.5(4) . . ?
O1 C12 C11 127.5(4) . . ?
C11 C12 C7 120.0 . . ?
C12 C11 C10 120.0 . . ?
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
C16 C18 1.4435(19) 2_676 ?
C16 C15 1.372(2) . ?
C16 C17 1.4443(18) . ?
C18 C17 1.342(2) . ?
C15 C13 1.4329(19) . ?
C15 C14 1.432(2) . ?
N1 C13 1.143(2) . ?
N2 C14 1.143(2) . ?
C3 C2 1.3900 . ?
C3 C4 1.3900 . ?
C2 C1 1.3900 . ?
C1 C6 1.3900 . ?
C1 O1 1.345(4) . ?
C6 C5 1.3900 . ?
C6 C7 1.422(3) . ?
C5 C4 1.3900 . ?
O1 C12 1.349(4) . ?
C10 C9 1.3900 . ?
C10 C11 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C12 1.3900 . ?
C12 C11 1.3900 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C18 C17 C16 -0.2(2) 2_676 . . . ?
C18 C16 C15 C13 -0.4(2) 2_676 . . . ?
C18 C16 C15 C14 -179.67(13) 2_676 . . . ?
C18 C16 C17 C18 0.2(2) 2_676 . . . ?
C15 C16 C17 C18 -179.84(13) . . . . ?
C17 C16 C15 C13 179.65(13) . . . . ?
C17 C16 C15 C14 0.4(2) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C2 C1 O1 -179.9(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C1 O1 C12 -179.5(3) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 C8 -180.0(2) . . . . ?
C1 C6 C7 C12 -0.5(3) . . . . ?
C1 O1 C12 C7 -0.9(3) . . . . ?
C1 O1 C12 C11 179.6(2) . . . . ?
C6 C1 O1 C12 0.6(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C12 O1 0.9(3) . . . . ?
C6 C7 C12 C11 -179.6(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C12 179.6(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
O1 C1 C6 C5 179.9(4) . . . . ?
O1 C1 C6 C7 0.0(3) . . . . ?
O1 C12 C11 C10 179.4(3) . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C8 C7 C6 179.4(3) . . . . ?
C9 C8 C7 C12 0.0 . . . . ?
C8 C7 C12 O1 -179.5(3) . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C7 C6 C5 C4 179.9(4) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
