#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228364.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_7228364
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), (C14 H8 N4)'
_chemical_formula_sum            'C40 H24 N4'
_chemical_formula_weight         560.66
_chemical_name_common            ([6]helicene)(Me2TCNQ)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 102.652(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4593(7)
_cell_length_b                   11.4032(6)
_cell_length_c                   17.8273(9)
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.30
_cell_volume                     2868.0(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 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7341
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0343
_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)+(0.0549P)²+1.3694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2687
_reflns_number_total             2929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00763a2.cif
_cod_data_source_block           6helicene-Me22TCNQ
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'C2/c  '
_cod_database_code               7228364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.46194(8) 0.86568(9) 0.87868(6) 0.0292(2) Uani 1 1 d .
H1 H 0.4668 0.9435 0.8946 0.035 Uiso 1 1 calc R
C2 C 0.54176(8) 0.80624(9) 0.86532(6) 0.0255(2) Uani 1 1 d .
H2 H 0.6005 0.8433 0.8758 0.031 Uiso 1 1 calc R
C3 C 0.37704(8) 0.80838(9) 0.86818(6) 0.0271(2) Uani 1 1 d .
H3 H 0.3248 0.8469 0.8790 0.032 Uiso 1 1 calc R
C4 C 0.53394(7) 0.69387(9) 0.83692(5) 0.0209(2) Uani 1 1 d .
H4 H 0.5877 0.6557 0.8287 0.025 Uiso 1 1 calc R
C5 C 0.36746(7) 0.69159(9) 0.84123(5) 0.0218(2) Uani 1 1 d .
C6 C 0.44549(7) 0.63511(8) 0.81994(5) 0.0192(2) Uani 1 1 d .
C7 C 0.28133(7) 0.62859(10) 0.83786(6) 0.0251(2) Uani 1 1 d .
H7 H 0.2294 0.6667 0.8496 0.030 Uiso 1 1 calc R
C8 C 0.27461(7) 0.51438(10) 0.81787(6) 0.0255(2) Uani 1 1 d .
H8 H 0.2198 0.4730 0.8200 0.031 Uiso 1 1 calc R
C9 C 0.35022(7) 0.45573(9) 0.79339(5) 0.0226(2) Uani 1 1 d .
C10 C 0.43213(6) 0.51884(8) 0.78635(5) 0.0194(2) Uani 1 1 d .
C11 C 0.34474(7) 0.33286(9) 0.77926(6) 0.0261(2) Uani 1 1 d .
H11 H 0.2891 0.2926 0.7803 0.031 Uiso 1 1 calc R
C12 C 0.42013(7) 0.27409(9) 0.76426(5) 0.0265(2) Uani 1 1 d .
H12 H 0.4197 0.1926 0.7633 0.032 Uiso 1 1 calc R
C13 C 0.5000 0.33604(12) 0.7500 0.0230(3) Uani 1 2 d S
C14 C 0.5000 0.46069(12) 0.7500 0.0200(3) Uani 1 2 d S
C15 C 0.49103(7) 0.61901(8) 0.47498(5) 0.0184(2) Uani 1 1 d .
C16 C 0.57985(6) 0.55638(8) 0.47868(5) 0.0186(2) Uani 1 1 d .
C17 C 0.58556(6) 0.44392(8) 0.50316(5) 0.0191(2) Uani 1 1 d .
H17 H 0.6426 0.4045 0.5061 0.023 Uiso 1 1 calc R
C18 C 0.47546(7) 0.73470(8) 0.45270(5) 0.0206(2) Uani 1 1 d .
C19 C 0.54318(7) 0.81401(8) 0.43302(6) 0.0237(2) Uani 1 1 d .
C20 C 0.38458(7) 0.78961(9) 0.44787(6) 0.0239(2) Uani 1 1 d .
C21 C 0.66373(7) 0.61018(9) 0.45476(6) 0.0242(2) Uani 1 1 d .
H21A H 0.7137 0.5533 0.4600 0.036 Uiso 1 1 calc R
H21B H 0.6855 0.6766 0.4868 0.036 Uiso 1 1 calc R
H21C H 0.6456 0.6350 0.4021 0.036 Uiso 1 1 calc R
N1 N 0.59203(7) 0.88468(8) 0.41677(6) 0.0319(2) Uani 1 1 d .
N2 N 0.31305(7) 0.83614(9) 0.44241(6) 0.0338(2) 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'
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 119.56(10) . .
C3 C1 H1 120.2 . .
C2 C1 H1 120.2 . .
C4 C2 C1 120.60(10) . .
C4 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C1 C3 C5 121.04(10) . .
C1 C3 H3 119.5 . .
C5 C3 H3 119.5 . .
C2 C4 C6 121.18(9) . .
C2 C4 H4 119.4 . .
C6 C4 H4 119.4 . .
C3 C5 C6 119.59(9) . .
C3 C5 C7 120.56(9) . .
C6 C5 C7 119.81(9) . .
C4 C6 C5 117.46(9) . .
C4 C6 C10 123.58(9) . .
C5 C6 C10 118.87(9) . .
C8 C7 C5 120.60(9) . .
C8 C7 H7 119.7 . .
C5 C7 H7 119.7 . .
C7 C8 C9 121.14(9) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C10 C9 C11 120.04(9) . .
C10 C9 C8 120.03(9) . .
C11 C9 C8 119.88(9) . .
C9 C10 C14 117.96(9) . .
C9 C10 C6 117.83(9) . .
C14 C10 C6 124.11(9) . .
C12 C11 C9 120.39(9) . .
C12 C11 H11 119.8 . .
C9 C11 H11 119.8 . .
C11 C12 C13 120.60(10) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C14 C13 C12 119.76(7) . .
C14 C13 C12 119.75(7) . 2_656
C12 C13 C12 120.49(13) . 2_656
C13 C14 C10 117.22(6) . 2_656
C13 C14 C10 117.22(6) . .
C10 C14 C10 125.55(12) 2_656 .
C18 C15 C17 117.77(9) . 5_666
C18 C15 C16 124.54(9) . .
C17 C15 C16 117.68(9) 5_666 .
C17 C16 C15 118.05(9) . .
C17 C16 C21 118.90(9) . .
C15 C16 C21 123.02(9) . .
C16 C17 C15 124.26(9) . 5_666
C16 C17 H17 117.9 . .
C15 C17 H17 117.9 5_666 .
C15 C18 C19 126.61(9) . .
C15 C18 C20 121.40(9) . .
C19 C18 C20 111.99(8) . .
N1 C19 C18 174.42(10) . .
N2 C20 C18 177.69(11) . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.3670(16) .
C1 C2 1.4030(15) .
C1 H1 0.9300 .
C2 C4 1.3733(14) .
C2 H2 0.9300 .
C3 C5 1.4123(15) .
C3 H3 0.9300 .
C4 C6 1.4165(13) .
C4 H4 0.9300 .
C5 C6 1.4211(13) .
C5 C7 1.4275(14) .
C6 C10 1.4502(13) .
C7 C8 1.3481(16) .
C7 H7 0.9300 .
C8 C9 1.4291(15) .
C8 H8 0.9300 .
C9 C10 1.4147(13) .
C9 C11 1.4227(15) .
C10 C14 1.4496(11) .
C11 C12 1.3553(15) .
C11 H11 0.9300 .
C12 C13 1.4233(12) .
C12 H12 0.9300 .
C13 C14 1.4213(19) .
C13 C12 1.4234(12) 2_656
C14 C10 1.4496(11) 2_656
C15 C18 1.3819(13) .
C15 C17 1.4430(13) 5_666
C15 C16 1.4584(13) .
C16 C17 1.3513(14) .
C16 C21 1.5018(13) .
C17 C15 1.4430(13) 5_666
C17 H17 0.9300 .
C18 C19 1.4319(14) .
C18 C20 1.4410(13) .
C19 N1 1.1497(14) .
C20 N2 1.1474(14) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203547
