#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228362.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_7228362
loop_
_publ_author_name
'Yoshida, Yukihiro'
'Nakamura, Yuto'
'Kishida, Hideo'
'Hayama, Hiromi'
'Nakano, Yoshiaki'
'Yamochi, Hideki'
'Saito, Gunzi'
_publ_section_title
;
 Racemic Charge-Transfer Complexes of Helical Polycyclic Aromatic
 Hydrocarbon Molecule
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00763A
_journal_year                    2017
_chemical_formula_moiety         '(C26 H16), (C12 F4 N4)'
_chemical_formula_sum            'C38 H16 F4 N4'
_chemical_formula_weight         604.57
_chemical_name_common            ([6]helicene)(F4TCNQ)
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-02-17 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1454(4)
_cell_length_b                   17.2601(9)
_cell_length_c                   22.2970(11)
_cell_measurement_reflns_used    8752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.36
_cell_volume                     2749.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13444
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+1.0215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                2477
_reflns_number_total             2811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00763a2.cif
_cod_data_source_block           6helicene-F4TCNQ
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'Pbcn '
_cod_database_code               7228362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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
C1 C 0.50690(19) 1.12839(7) 0.62494(5) 0.0228(3) Uani 1 1 d .
H1 H 0.4829 1.1762 0.6072 0.027 Uiso 1 1 calc R
C2 C 0.36552(17) 1.08973(7) 0.65650(5) 0.0208(3) Uani 1 1 d .
H2 H 0.2465 1.1114 0.6588 0.025 Uiso 1 1 calc R
C3 C 0.68095(18) 1.09539(7) 0.62029(6) 0.0229(3) Uani 1 1 d .
H3 H 0.7743 1.1210 0.5991 0.027 Uiso 1 1 calc R
C4 C 0.40131(16) 1.01993(6) 0.68413(5) 0.0182(2) Uani 1 1 d .
H4 H 0.3056 0.9950 0.7048 0.022 Uiso 1 1 calc R
C5 C 0.72087(17) 1.02298(7) 0.64720(5) 0.0195(3) Uani 1 1 d .
C6 C 0.58078(16) 0.98533(6) 0.68174(5) 0.0169(2) Uani 1 1 d .
C7 C 0.89657(17) 0.98521(7) 0.63763(6) 0.0240(3) Uani 1 1 d .
H7 H 0.9933 1.0118 0.6188 0.029 Uiso 1 1 calc R
C8 C 0.92372(18) 0.91110(7) 0.65567(6) 0.0244(3) Uani 1 1 d .
H8 H 1.0353 0.8862 0.6463 0.029 Uiso 1 1 calc R
C9 C 0.78353(17) 0.87071(7) 0.68891(5) 0.0204(3) Uani 1 1 d .
C10 C 0.62301(16) 0.91059(6) 0.70854(5) 0.0172(2) Uani 1 1 d .
C11 C 0.80058(18) 0.78958(7) 0.70025(6) 0.0240(3) Uani 1 1 d .
H11 H 0.9109 0.7639 0.6906 0.029 Uiso 1 1 calc R
C12 C 0.65641(18) 0.74983(7) 0.72510(6) 0.0245(3) Uani 1 1 d .
H12 H 0.6596 0.6960 0.7259 0.029 Uiso 1 1 calc R
C13 C 0.5000 0.78977(9) 0.7500 0.0207(3) Uani 1 2 d S
C14 C 0.5000 0.87176(9) 0.7500 0.0178(3) Uani 1 2 d S
C15 C 0.53725(16) 0.92347(6) 0.52511(5) 0.0166(2) Uani 1 1 d .
C16 C 0.35895(16) 0.96186(7) 0.52985(5) 0.0177(2) Uani 1 1 d .
C17 C 0.32488(15) 1.03251(7) 0.50736(5) 0.0177(2) Uani 1 1 d .
C18 C 0.57132(17) 0.85143(6) 0.54917(5) 0.0190(2) Uani 1 1 d .
C19 C 0.43761(18) 0.80881(7) 0.58458(6) 0.0223(3) Uani 1 1 d .
C20 C 0.74409(18) 0.81033(7) 0.54053(5) 0.0225(3) Uani 1 1 d .
N1 N 0.33933(17) 0.77171(7) 0.61309(5) 0.0319(3) Uani 1 1 d .
N2 N 0.87682(17) 0.77402(6) 0.53429(5) 0.0311(3) Uani 1 1 d .
F1 F 0.21990(10) 0.92406(4) 0.55689(3) 0.02603(19) Uani 1 1 d .
F2 F 0.15421(9) 1.06276(4) 0.51412(3) 0.02516(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'
N N 0.0061 0.0033 '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
C3 C1 C2 119.61(11) . .
C3 C1 H1 120.2 . .
C2 C1 H1 120.2 . .
C4 C2 C1 120.51(11) . .
C4 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C1 C3 C5 121.15(11) . .
C1 C3 H3 119.4 . .
C5 C3 H3 119.4 . .
C2 C4 C6 121.36(11) . .
C2 C4 H4 119.3 . .
C6 C4 H4 119.3 . .
C3 C5 C6 119.46(11) . .
C3 C5 C7 121.06(11) . .
C6 C5 C7 119.40(11) . .
C4 C6 C5 117.76(10) . .
C4 C6 C10 123.16(10) . .
C5 C6 C10 118.86(10) . .
C8 C7 C5 120.76(11) . .
C8 C7 H7 119.6 . .
C5 C7 H7 119.6 . .
C7 C8 C9 120.97(11) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C10 C9 C8 119.63(11) . .
C10 C9 C11 119.60(11) . .
C8 C9 C11 120.71(11) . .
C9 C10 C14 117.98(11) . .
C9 C10 C6 118.38(10) . .
C14 C10 C6 123.36(10) . .
C12 C11 C9 120.24(11) . .
C12 C11 H11 119.9 . .
C9 C11 H11 119.9 . .
C11 C12 C13 120.67(12) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C14 C13 C12 118.91(8) . 3_656
C14 C13 C12 118.91(8) . .
C12 C13 C12 122.17(15) 3_656 .
C13 C14 C10 117.72(7) . .
C13 C14 C10 117.72(7) . 3_656
C10 C14 C10 124.57(14) . 3_656
C18 C15 C17 123.51(11) . 5_676
C18 C15 C16 122.93(11) . .
C17 C15 C16 113.55(10) 5_676 .
F1 C16 C17 118.63(10) . .
F1 C16 C15 117.88(10) . .
C17 C16 C15 123.48(11) . .
F2 C17 C16 118.63(10) . .
F2 C17 C15 118.39(10) . 5_676
C16 C17 C15 122.95(11) . 5_676
C15 C18 C20 123.08(11) . .
C15 C18 C19 123.89(11) . .
C20 C18 C19 113.02(10) . .
N1 C19 C18 175.99(13) . .
N2 C20 C18 176.38(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.3718(19) .
C1 C2 1.4004(17) .
C1 H1 0.9300 .
C2 C4 1.3771(17) .
C2 H2 0.9300 .
C3 C5 1.4155(17) .
C3 H3 0.9300 .
C4 C6 1.4156(16) .
C4 H4 0.9300 .
C5 C6 1.4203(16) .
C5 C7 1.4306(17) .
C6 C10 1.4534(16) .
C7 C8 1.3550(18) .
C7 H7 0.9300 .
C8 C9 1.4278(17) .
C8 H8 0.9300 .
C9 C10 1.4074(16) .
C9 C11 1.4282(17) .
C10 C14 1.4408(13) .
C11 C12 1.3560(18) .
C11 H11 0.9300 .
C12 C13 1.4257(15) .
C12 H12 0.9300 .
C13 C14 1.415(2) .
C13 C12 1.4256(15) 3_656
C14 C10 1.4409(13) 3_656
C15 C18 1.3759(16) .
C15 C17 1.4393(16) 5_676
C15 C16 1.4400(16) .
C16 F1 1.3327(13) .
C16 C17 1.3409(17) .
C17 F2 1.3351(13) .
C17 C15 1.4393(16) 5_676
C18 C20 1.4368(17) .
C18 C19 1.4413(17) .
C19 N1 1.1433(17) .
C20 N2 1.1453(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203545
