#------------------------------------------------------------------------------
#$Date: 2022-02-22 01:33:35 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244455.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_7244455
loop_
_publ_author_name
'Mandal, Arkalekha'
_publ_section_title
;
 Tuning p-type to n-type semiconductor nature by charge transfer
 cocrystallization: effect of transfer integral vs. reorganization energy
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00006G
_journal_year                    2022
_chemical_formula_sum            'C60 H32 N10'
_chemical_formula_weight         892.95
_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
_audit_creation_method           'APEX2 v2014.3-0'
_audit_update_record
;
2021-01-27 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.958(13)
_cell_angle_beta                 96.022(13)
_cell_angle_gamma                92.421(13)
_cell_formula_units_Z            1
_cell_length_a                   6.7820(13)
_cell_length_b                   9.3889(17)
_cell_length_c                   17.885(3)
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.30
_cell_volume                     1126.8(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.933
_diffrn_reflns_theta_min         1.150
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5824
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0688
_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)+(0.1083P)²+0.1587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.2286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2743
_reflns_number_total             5824
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00006g2.cif
_cod_data_source_block           CBPTCNQ
_cod_database_code               7244455
_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   0.998
_shelxl_version_number           2013-4
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
C1 C 0.4016(4) 0.2707(3) 0.21088(13) 0.0393(6) Uani 1 1 d . . . . .
C2 C 0.3809(4) 0.1348(3) 0.17238(16) 0.0518(7) Uani 1 1 d . . . . .
H2 H 0.3833 0.0529 0.1982 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3568(4) 0.1261(3) 0.09499(16) 0.0574(8) Uani 1 1 d . . . . .
H3 H 0.3419 0.0362 0.0681 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3539(4) 0.2474(3) 0.05526(16) 0.0541(7) Uani 1 1 d . . . . .
H4 H 0.3379 0.2373 0.0028 0.065 Uiso 1 1 calc R U . . .
C5 C 0.3746(4) 0.3814(3) 0.09306(14) 0.0465(7) Uani 1 1 d . . . . .
H5 H 0.3722 0.4624 0.0665 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3992(3) 0.3949(3) 0.17188(14) 0.0380(6) Uani 1 1 d . . . . .
C7 C 0.4229(3) 0.5156(3) 0.22810(13) 0.0373(6) Uani 1 1 d . . . . .
C8 C 0.4308(4) 0.6635(3) 0.22464(16) 0.0479(7) Uani 1 1 d . . . . .
H8 H 0.4206 0.7024 0.1784 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4539(4) 0.7507(3) 0.29132(17) 0.0554(8) Uani 1 1 d . . . . .
H9 H 0.4593 0.8496 0.2899 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4693(4) 0.6932(3) 0.36054(17) 0.0559(8) Uani 1 1 d . . . . .
H10 H 0.4842 0.7549 0.4046 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4632(4) 0.5479(3) 0.36607(15) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.4746 0.5102 0.4126 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4394(4) 0.4603(3) 0.29899(14) 0.0390(6) Uani 1 1 d . . . . .
C13 C 0.4463(3) 0.2192(2) 0.34871(10) 0.0406(6) Uani 1 1 d DG . . . .
C14 C 0.6226(3) 0.1522(3) 0.36489(14) 0.0967(14) Uani 1 1 d G . . A .
H14 H 0.7268 0.1647 0.3358 0.116 Uiso 1 1 calc R U . . .
C15 C 0.6432(3) 0.0666(3) 0.42458(14) 0.0925(14) Uani 1 1 d G . . A .
H15 H 0.7612 0.0218 0.4354 0.111 Uiso 1 1 calc R U . . .
C16 C 0.4875(3) 0.0480(2) 0.46809(9) 0.0375(6) Uani 1 1 d DG . . A .
C17 C 0.3112(3) 0.1150(4) 0.45191(16) 0.0684(17) Uani 0.803(8) 1 d G . P A 1
H17 H 0.2070 0.1025 0.4810 0.082 Uiso 0.803(8) 1 calc R U P A 1
C18 C 0.2906(3) 0.2006(4) 0.39222(16) 0.0700(17) Uani 0.803(8) 1 d G . P A 1
H18 H 0.1726 0.2454 0.3814 0.084 Uiso 0.803(8) 1 calc R U P A 1
C17* C 0.3105(10) 0.0507(13) 0.4217(6) 0.040(4) Uani 0.197(8) 1 d D . P A 2
H17* H 0.2032 -0.0068 0.4318 0.047 Uiso 0.197(8) 1 calc R U P A 2
C18* C 0.2832(10) 0.1338(12) 0.3612(7) 0.052(5) Uani 0.197(8) 1 d D . P A 2
H18* H 0.1628 0.1322 0.3309 0.063 Uiso 0.197(8) 1 calc R U P A 2
C19 C 0.8932(4) 0.3416(3) 0.15124(14) 0.0407(6) Uani 1 1 d . . . . .
C20 C 0.8972(4) 0.4882(3) 0.13266(15) 0.0442(6) Uani 1 1 d . . . . .
H20 H 0.8847 0.5070 0.0822 0.053 Uiso 1 1 calc R U . . .
C21 C 0.9184(4) 0.5976(3) 0.18644(15) 0.0466(7) Uani 1 1 d . . . . .
H21 H 0.9201 0.6910 0.1728 0.056 Uiso 1 1 calc R U . . .
C22 C 0.9387(4) 0.5729(3) 0.26517(15) 0.0440(6) Uani 1 1 d . . . . .
C23 C 0.9376(4) 0.4271(3) 0.28413(15) 0.0441(6) Uani 1 1 d . . . . .
H23 H 0.9517 0.4086 0.3346 0.053 Uiso 1 1 calc R U . . .
C24 C 0.9165(4) 0.3171(3) 0.23007(14) 0.0425(6) Uani 1 1 d . . . . .
H24 H 0.9170 0.2237 0.2438 0.051 Uiso 1 1 calc R U . . .
C25 C 0.9600(4) 0.6853(3) 0.32056(16) 0.0515(7) Uani 1 1 d . . . . .
C26 C 0.9621(5) 0.8315(3) 0.30381(18) 0.0631(8) Uani 1 1 d . . . . .
C27 C 0.9816(5) 0.6666(3) 0.39936(19) 0.0610(8) Uani 1 1 d . . . . .
C28 C 0.8660(4) 0.2304(3) 0.09555(14) 0.0428(6) Uani 1 1 d . . . . .
C29 C 0.8409(4) 0.2549(3) 0.01730(17) 0.0525(7) Uani 1 1 d . . . . .
C30 C 0.8546(4) 0.0823(3) 0.10991(16) 0.0514(7) Uani 1 1 d . . . . .
N1 N 0.4266(3) 0.3109(2) 0.28832(11) 0.0417(5) Uani 1 1 d . . . . .
N2 N 0.9645(5) 0.9494(3) 0.29324(19) 0.0923(10) Uani 1 1 d . . . . .
N3 N 0.9981(5) 0.6575(4) 0.46298(18) 0.0923(10) Uani 1 1 d . . . . .
N4 N 0.8192(4) 0.2748(3) -0.04524(16) 0.0752(8) Uani 1 1 d . . . . .
N5 N 0.8422(5) -0.0365(3) 0.11826(16) 0.0766(8) 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
_geom_angle_publ_flag
C2 C1 N1 129.7(2) . . ?
C2 C1 C6 121.3(2) . . ?
N1 C1 C6 109.0(2) . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 133.7(2) . . ?
C1 C6 C7 106.9(2) . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 C6 133.7(2) . . ?
C12 C7 C6 106.9(2) . . ?
C9 C8 C7 118.5(3) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 116.9(2) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C11 C12 N1 128.7(2) . . ?
C11 C12 C7 122.3(2) . . ?
N1 C12 C7 109.0(2) . . ?
C18* C13 C14 111.4(5) . . ?
C14 C13 C18 120.0 . . ?
C18* C13 N1 118.8(4) . . ?
C14 C13 N1 120.10(14) . . ?
C18 C13 N1 119.88(14) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17* C16 C15 108.2(5) . . ?
C17 C16 C15 120.0 . . ?
C17* C16 C16 122.5(5) . 2_656 ?
C17 C16 C16 121.1(2) . 2_656 ?
C15 C16 C16 118.9(2) . 2_656 ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C16 C17* C18* 124.3(9) . . ?
C16 C17* H17* 117.9 . . ?
C18* C17* H17* 117.9 . . ?
C13 C18* C17* 115.9(9) . . ?
C13 C18* H18* 122.0 . . ?
C17* C18* H18* 122.0 . . ?
C28 C19 C24 121.6(2) . . ?
C28 C19 C20 120.8(2) . . ?
C24 C19 C20 117.6(2) . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C25 C22 C23 121.0(2) . . ?
C25 C22 C21 121.1(2) . . ?
C23 C22 C21 117.9(2) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C19 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C22 C25 C27 123.2(3) . . ?
C22 C25 C26 122.5(3) . . ?
C27 C25 C26 114.2(3) . . ?
N2 C26 C25 177.5(4) . . ?
N3 C27 C25 177.2(3) . . ?
C19 C28 C29 121.6(2) . . ?
C19 C28 C30 123.8(2) . . ?
C29 C28 C30 114.6(2) . . ?
N4 C29 C28 179.4(3) . . ?
N5 C30 C28 177.1(3) . . ?
C1 N1 C12 108.15(19) . . ?
C1 N1 C13 127.7(2) . . ?
C12 N1 C13 124.0(2) . . ?
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
C1 C2 1.391(4) . ?
C1 N1 1.395(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.406(3) . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.397(3) . ?
C13 C18* 1.387(2) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 N1 1.437(2) . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17* 1.389(2) . ?
C16 C17 1.3900 . ?
C16 C16 1.514(2) 2_656 ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C17* C18* 1.389(2) . ?
C17* H17* 0.9300 . ?
C18* H18* 0.9300 . ?
C19 C28 1.371(4) . ?
C19 C24 1.441(3) . ?
C19 C20 1.444(3) . ?
C20 C21 1.337(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.440(4) . ?
C21 H21 0.9300 . ?
C22 C25 1.375(4) . ?
C22 C23 1.439(4) . ?
C23 C24 1.345(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.428(4) . ?
C25 C26 1.430(4) . ?
C26 N2 1.138(4) . ?
C27 N3 1.143(4) . ?
C28 C29 1.431(4) . ?
C28 C30 1.436(4) . ?
C29 N4 1.145(3) . ?
C30 N5 1.139(3) . ?
