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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/74/7237403.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_7237403
loop_
_publ_author_name
'Wang, Jing'
'Li, Aisen'
'Xu, Shuping'
'Li, Bao'
'Song, Chongping'
'Geng, Yijia'
'Chu, Ning'
'He, Jian'
'Xu, Weiqing'
_publ_section_title
;
 Tunable luminescence of a novel organic co-crystal based on
 intermolecular charge transfer under pressure
;
_journal_issue                   33
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8958
_journal_paper_doi               10.1039/C8TC02748J
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         '2(C16 H12 O), C8 N2 F4'
_chemical_formula_sum            'C40 H24 F4 N2 O2'
_chemical_formula_weight         640.61
_chemical_name_common            9ACA-TFP
_chemical_name_systematic
9-acetylanthracene-tetrafluoroterephthalonitrile
_chemical_properties_physical    Deliquescent
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6109(4)
_cell_length_b                   10.4279(4)
_cell_length_c                   13.0037(5)
_cell_measurement_reflns_used    6948
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.98
_cell_volume                     1568.34(10)
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_collection       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      119
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18354
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0539
_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)+(0.0556P)²+0.4243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2254
_reflns_number_total             3836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc02748j2.cif
_cod_data_source_block           mo_wj_6_o_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7237403
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.53502(16) 0.4802(2) 0.40313(15) 0.0604(5) Uani 1 1 d . .
C2 C 0.50395(17) 0.5999(2) 0.43250(15) 0.0625(5) Uani 1 1 d . .
C3 C 0.46813(16) 0.62187(19) 0.53003(16) 0.0600(5) Uani 1 1 d . .
C4 C 0.4359(2) 0.7486(3) 0.5615(2) 0.0792(7) Uani 1 1 d . .
C5 C 0.15669(15) 0.60364(18) 0.45491(14) 0.0526(5) Uani 1 1 d . .
C6 C 0.14070(18) 0.7190(2) 0.39558(18) 0.0689(6) Uani 1 1 d . .
H6 H 0.1543 0.7178 0.3246 0.083 Uiso 1 1 calc R U
C7 C 0.1068(2) 0.8291(2) 0.4380(2) 0.0840(7) Uani 1 1 d . .
H7 H 0.0970 0.9042 0.3968 0.101 Uiso 1 1 calc R U
C8 C 0.0856(2) 0.8338(2) 0.5425(2) 0.0872(8) Uani 1 1 d . .
H8 H 0.0609 0.9118 0.5711 0.105 Uiso 1 1 calc R U
C9 C 0.10012(19) 0.7287(2) 0.60278(19) 0.0747(6) Uani 1 1 d . .
H9 H 0.0869 0.7343 0.6737 0.090 Uiso 1 1 calc R U
C10 C 0.13507(15) 0.60870(19) 0.56173(15) 0.0561(5) Uani 1 1 d . .
C11 C 0.14861(17) 0.4978(2) 0.62077(15) 0.0610(5) Uani 1 1 d . .
H11 H 0.1340 0.5016 0.6914 0.073 Uiso 1 1 calc R U
C12 C 0.18262(16) 0.38204(19) 0.58078(14) 0.0558(5) Uani 1 1 d . .
C13 C 0.19700(19) 0.2685(2) 0.64173(18) 0.0737(6) Uani 1 1 d . .
H13 H 0.1820 0.2713 0.7123 0.088 Uiso 1 1 calc R U
C14 C 0.2314(2) 0.1575(2) 0.6014(2) 0.0847(7) Uani 1 1 d . .
H14 H 0.2404 0.0831 0.6435 0.102 Uiso 1 1 calc R U
C15 C 0.2540(2) 0.1515(2) 0.4975(2) 0.0844(7) Uani 1 1 d . .
H15 H 0.2784 0.0726 0.4700 0.101 Uiso 1 1 calc R U
C16 C 0.24158(19) 0.2556(2) 0.43563(17) 0.0684(6) Uani 1 1 d . .
H16 H 0.2573 0.2487 0.3654 0.082 Uiso 1 1 calc R U
C17 C 0.20519(15) 0.37610(18) 0.47418(14) 0.0522(5) Uani 1 1 d . .
C18 C 0.19171(15) 0.48744(18) 0.41386(13) 0.0501(4) Uani 1 1 d . .
C19 C 0.21579(18) 0.4820(2) 0.30188(15) 0.0603(5) Uani 1 1 d . .
C20 C 0.1222(2) 0.4367(3) 0.22600(17) 0.0962(9) Uani 1 1 d . .
H20A H 0.0622 0.5026 0.2164 0.144 Uiso 1 1 calc R U
H20B H 0.0887 0.3578 0.2514 0.144 Uiso 1 1 calc R U
H20C H 0.1539 0.4195 0.1599 0.144 Uiso 1 1 calc R U
F1 F 0.56819(11) 0.46179(14) 0.30840(9) 0.0877(5) Uani 1 1 d . .
F2 F 0.50741(13) 0.69758(13) 0.36700(11) 0.0923(5) Uani 1 1 d . .
N1 N 0.4104(2) 0.8472(2) 0.5883(2) 0.1112(8) Uani 1 1 d . .
O1 O 0.30633(14) 0.5167(2) 0.27400(12) 0.1029(7) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
F1 C1 C2 119.65(19) . .
F1 C1 C3 119.77(19) . 3_666
C2 C1 C3 120.57(19) . 3_666
F2 C2 C1 119.87(19) . .
F2 C2 C3 119.1(2) . .
C1 C2 C3 121.02(18) . .
C1 C3 C2 118.41(19) 3_666 .
C1 C3 C4 120.5(2) 3_666 .
C2 C3 C4 121.1(2) . .
N1 C4 C3 178.5(3) . .
C18 C5 C6 123.37(18) . .
C18 C5 C10 118.89(17) . .
C6 C5 C10 117.74(18) . .
C7 C6 C5 121.5(2) . .
C7 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C6 C7 C8 120.6(2) . .
C6 C7 H7 119.7 . .
C8 C7 H7 119.7 . .
C9 C8 C7 120.7(2) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 121.2(2) . .
C8 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C11 C10 C9 122.86(19) . .
C11 C10 C5 118.94(17) . .
C9 C10 C5 118.20(19) . .
C12 C11 C10 122.67(17) . .
C12 C11 H11 118.7 . .
C10 C11 H11 118.7 . .
C11 C12 C13 122.54(19) . .
C11 C12 C17 118.85(17) . .
C13 C12 C17 118.60(19) . .
C14 C13 C12 121.4(2) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C13 C14 C15 120.1(2) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 121.3(2) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C15 C16 C17 121.1(2) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C18 C17 C16 123.59(17) . .
C18 C17 C12 118.93(17) . .
C16 C17 C12 117.47(18) . .
C5 C18 C17 121.72(16) . .
C5 C18 C19 119.06(17) . .
C17 C18 C19 119.22(17) . .
O1 C19 C20 120.47(19) . .
O1 C19 C18 121.56(18) . .
C20 C19 C18 117.94(18) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.336(2) .
C1 C2 1.363(3) .
C1 C3 1.377(3) 3_666
C2 F2 1.331(2) .
C2 C3 1.388(3) .
C3 C1 1.377(3) 3_666
C3 C4 1.442(3) .
C4 N1 1.134(3) .
C5 C18 1.399(3) .
C5 C6 1.432(3) .
C5 C10 1.434(3) .
C6 C7 1.348(3) .
C6 H6 0.9500 .
C7 C8 1.402(4) .
C7 H7 0.9500 .
C8 C9 1.349(3) .
C8 H8 0.9500 .
C9 C10 1.433(3) .
C9 H9 0.9500 .
C10 C11 1.389(3) .
C11 C12 1.386(3) .
C11 H11 0.9500 .
C12 C13 1.426(3) .
C12 C17 1.435(3) .
C13 C14 1.346(3) .
C13 H13 0.9500 .
C14 C15 1.400(4) .
C14 H14 0.9500 .
C15 C16 1.352(3) .
C15 H15 0.9500 .
C16 C17 1.430(3) .
C16 H16 0.9500 .
C17 C18 1.402(3) .
C18 C19 1.508(3) .
C19 O1 1.198(2) .
C19 C20 1.479(3) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340003
