#------------------------------------------------------------------------------
#$Date: 2021-11-06 21:56:26 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270441 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243492.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_7243492
loop_
_publ_author_name
'Mandal, Arkalekha'
'Kim, Youngmee'
'Kim, Sung-Jin'
'Park, JaeHong'
_publ_section_title
;
 Unravelling the fluorescence and semiconductor properties of a new
 coronene:TCNB charge transfer cocrystal polymorph
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              7132
_journal_page_last               7140
_journal_paper_doi               10.1039/D1CE00741F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C39 H15 N6'
_chemical_formula_weight         567.57
_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           SHELXL-2013
_audit_update_record
;
2021-05-20 deposited with the CCDC.	2021-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                78.231(12)
_cell_angle_beta                 89.490(13)
_cell_angle_gamma                77.581(13)
_cell_formula_units_Z            2
_cell_length_a                   7.3212(14)
_cell_length_b                   9.9861(19)
_cell_length_c                   19.292(3)
_cell_measurement_reflns_used    2562
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4320
_cell_measurement_theta_min      2.1581
_cell_volume                     1347.6(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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.1593
_diffrn_reflns_av_unetI/netI     0.1589
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.544
_diffrn_reflns_theta_min         2.134
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       neddle
_exptl_crystal_F_000             582
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0663
_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)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3212
_reflns_number_total             6812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00741f2.cif
_cod_data_source_block           CocrystalI
_cod_depositor_comments          'Adding full bibliography for 7243492.cif.'
_cod_original_cell_volume        1347.5(4)
_cod_database_code               7243492
_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 1.0017(4) 0.2090(3) 0.65670(14) 0.0361(7) Uani 1 1 d . . . . .
H1 H 1.0362 0.1458 0.7008 0.043 Uiso 1 1 calc R U . . .
C2 C 0.8483(4) 0.2002(3) 0.61889(14) 0.0365(7) Uani 1 1 d . . . . .
H2 H 0.7793 0.1311 0.6371 0.044 Uiso 1 1 calc R U . . .
C3 C 0.7915(4) 0.2933(3) 0.55292(14) 0.0332(7) Uani 1 1 d . . . . .
C4 C 0.6346(4) 0.2858(3) 0.51303(14) 0.0354(7) Uani 1 1 d . . . . .
H4 H 0.5653 0.2163 0.5300 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5809(4) 0.3796(3) 0.44918(14) 0.0328(7) Uani 1 1 d . . . . .
H5 H 0.4738 0.3740 0.4234 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6825(4) 0.4834(3) 0.42163(13) 0.0322(6) Uani 1 1 d . . . . .
C7 C 0.6304(4) 0.5804(3) 0.35637(14) 0.0358(7) Uani 1 1 d . . . . .
H7 H 0.5235 0.5764 0.3300 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7310(4) 0.6795(3) 0.33071(14) 0.0352(7) Uani 1 1 d . . . . .
H8 H 0.6928 0.7423 0.2867 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8906(4) 0.6908(3) 0.36809(14) 0.0340(7) Uani 1 1 d . . . . .
C10 C 0.9457(4) 0.5951(3) 0.43406(13) 0.0291(6) Uani 1 1 d . . . . .
C11 C 0.8414(4) 0.4918(3) 0.46024(13) 0.0301(6) Uani 1 1 d . . . . .
C12 C 0.8961(4) 0.3965(3) 0.52682(13) 0.0297(6) Uani 1 1 d . . . . .
C13 C -0.0311(4) 0.7259(3) -0.10187(16) 0.0445(8) Uani 1 1 d . . . . .
H13 H -0.0190 0.6370 -0.1140 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0481(4) 0.7337(3) -0.03710(14) 0.0358(7) Uani 1 1 d . . . . .
C15 C 0.1506(4) 0.6146(3) 0.01161(17) 0.0459(8) Uani 1 1 d . . . . .
H15 H 0.1729 0.5254 -0.0009 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2170(4) 0.6249(3) 0.07515(16) 0.0438(8) Uani 1 1 d . . . . .
H16 H 0.2836 0.5427 0.1062 0.053 Uiso 1 1 calc R U . . .
C17 C 0.1898(4) 0.7555(3) 0.09659(14) 0.0345(7) Uani 1 1 d . . . . .
C18 C 0.2582(4) 0.7699(3) 0.16271(15) 0.0419(7) Uani 1 1 d . . . . .
H18 H 0.3187 0.6887 0.1959 0.050 Uiso 1 1 calc R U . . .
C19 C 0.2382(4) 0.8982(3) 0.17924(14) 0.0423(7) Uani 1 1 d . . . . .
H19 H 0.2869 0.9048 0.2236 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1467(4) 1.0223(3) 0.13193(13) 0.0341(7) Uani 1 1 d . . . . .
C21 C 0.1242(4) 1.1581(3) 0.14756(15) 0.0423(8) Uani 1 1 d . . . . .
H21 H 0.1756 1.1677 0.1909 0.051 Uiso 1 1 calc R U . . .
C22 C 0.0725(3) 1.0107(3) 0.06632(12) 0.0268(6) Uani 1 1 d . . . . .
C23 C 0.0957(3) 0.8770(3) 0.04853(13) 0.0272(6) Uani 1 1 d . . . . .
C24 C 0.0234(3) 0.8666(3) -0.01806(13) 0.0285(6) Uani 1 1 d . . . . .
C25 C 0.7204(4) 0.2749(3) 0.26091(13) 0.0292(6) Uani 1 1 d . . . . .
C26 C 0.8626(4) 0.3472(3) 0.26026(13) 0.0300(6) Uani 1 1 d . . . . .
H26 H 0.8698 0.4222 0.2219 0.036 Uiso 1 1 calc R U . . .
C27 C 0.9943(4) 0.3090(3) 0.31610(13) 0.0288(6) Uani 1 1 d . . . . .
C28 C 0.9812(4) 0.1992(3) 0.37373(13) 0.0299(6) Uani 1 1 d . . . . .
C29 C 0.8350(4) 0.1304(3) 0.37543(13) 0.0323(6) Uani 1 1 d . . . . .
H29 H 0.8241 0.0585 0.4149 0.039 Uiso 1 1 calc R U . . .
C30 C 0.7040(4) 0.1672(3) 0.31889(13) 0.0298(6) Uani 1 1 d . . . . .
C31 C 0.5946(4) 0.3058(3) 0.19988(15) 0.0339(7) Uani 1 1 d . . . . .
C32 C 1.1466(4) 0.3804(3) 0.31149(13) 0.0332(6) Uani 1 1 d . . . . .
C33 C 1.1178(4) 0.1569(3) 0.43218(14) 0.0322(6) Uani 1 1 d . . . . .
C34 C 0.5492(4) 0.0999(3) 0.32004(13) 0.0328(6) Uani 1 1 d . . . . .
C35 C 0.5778(3) -0.0053(3) 0.06610(12) 0.0255(6) Uani 1 1 d . . . . .
C36 C 0.4927(3) 0.1239(3) 0.02468(12) 0.0261(6) Uani 1 1 d . . . . .
H36 H 0.4888 0.2076 0.0414 0.031 Uiso 1 1 calc R U . . .
C37 C 0.4133(3) 0.1296(3) -0.04134(12) 0.0263(6) Uani 1 1 d . . . . .
C38 C 0.6585(4) -0.0111(3) 0.13486(13) 0.0282(6) Uani 1 1 d . . . . .
C39 C 0.3251(4) 0.2627(3) -0.08501(13) 0.0288(6) Uani 1 1 d . . . . .
N1 N 0.5012(3) 0.3252(2) 0.14990(13) 0.0414(6) Uani 1 1 d . . . . .
N2 N 1.2691(4) 0.4362(3) 0.30380(12) 0.0428(6) Uani 1 1 d . . . . .
N3 N 1.2261(3) 0.1224(2) 0.47810(12) 0.0440(6) Uani 1 1 d . . . . .
N4 N 0.4200(3) 0.0516(3) 0.31946(12) 0.0418(6) Uani 1 1 d . . . . .
N5 N 0.7238(3) -0.0160(2) 0.18945(11) 0.0348(6) Uani 1 1 d . . . . .
N6 N 0.2543(3) 0.3692(2) -0.11977(12) 0.0377(6) 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 C9 121.8(3) . 2_766 ?
C2 C1 H1 119.1 . . ?
C9 C1 H1 119.1 2_766 . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 C12 119.5(2) . . ?
C2 C3 C12 118.7(2) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C11 C6 C5 119.2(2) . . ?
C11 C6 C7 118.4(2) . . ?
C5 C6 C7 122.5(2) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C1 C9 C8 123.3(3) 2_766 . ?
C1 C9 C10 118.5(2) 2_766 . ?
C8 C9 C10 118.2(2) . . ?
C12 C10 C11 120.2(2) 2_766 . ?
C12 C10 C9 119.9(2) 2_766 . ?
C11 C10 C9 119.9(2) . . ?
C6 C11 C10 120.4(2) . . ?
C6 C11 C12 119.7(2) . . ?
C10 C11 C12 119.9(2) . . ?
C10 C12 C3 120.3(2) 2_766 . ?
C10 C12 C11 119.9(2) 2_766 . ?
C3 C12 C11 119.8(2) . . ?
C21 C13 C14 121.8(3) 2_575 . ?
C21 C13 H13 119.1 2_575 . ?
C14 C13 H13 119.1 . . ?
C13 C14 C24 118.8(3) . . ?
C13 C14 C15 123.5(3) . . ?
C24 C14 C15 117.7(2) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 121.7(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C23 C17 C18 118.8(3) . . ?
C23 C17 C16 118.1(3) . . ?
C18 C17 C16 123.1(3) . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.7(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C22 C20 C19 118.6(3) . . ?
C22 C20 C21 118.4(3) . . ?
C19 C20 C21 123.0(3) . . ?
C13 C21 C20 121.3(3) 2_575 . ?
C13 C21 H21 119.3 2_575 . ?
C20 C21 H21 119.3 . . ?
C20 C22 C23 119.8(2) . . ?
C20 C22 C24 120.0(2) . 2_575 ?
C23 C22 C24 120.2(2) . 2_575 ?
C17 C23 C22 120.1(2) . . ?
C17 C23 C24 120.5(2) . . ?
C22 C23 C24 119.4(2) . . ?
C14 C24 C23 120.1(2) . . ?
C14 C24 C22 119.6(2) . 2_575 ?
C23 C24 C22 120.4(2) . 2_575 ?
C26 C25 C30 120.7(2) . . ?
C26 C25 C31 119.4(2) . . ?
C30 C25 C31 119.9(2) . . ?
C25 C26 C27 119.5(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.2(2) . . ?
C26 C27 C32 118.0(2) . . ?
C28 C27 C32 121.8(2) . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 C33 118.7(2) . . ?
C27 C28 C33 121.1(2) . . ?
C28 C29 C30 119.7(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 C34 120.8(2) . . ?
C25 C30 C34 119.5(2) . . ?
N1 C31 C25 176.4(3) . . ?
N2 C32 C27 176.0(3) . . ?
N3 C33 C28 179.4(3) . . ?
N4 C34 C30 176.9(3) . . ?
C36 C35 C37 120.6(2) . 2_655 ?
C36 C35 C38 119.4(2) . . ?
C37 C35 C38 120.0(2) 2_655 . ?
C37 C36 C35 119.5(2) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C35 119.9(2) . 2_655 ?
C36 C37 C39 120.2(2) . . ?
C35 C37 C39 119.9(2) 2_655 . ?
N5 C38 C35 179.6(3) . . ?
N6 C39 C37 179.8(3) . . ?
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 1.372(4) . ?
C1 C9 1.411(4) 2_766 ?
C1 H1 0.9500 . ?
C2 C3 1.420(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(4) . ?
C3 C12 1.422(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(4) . ?
C5 H5 0.9500 . ?
C6 C11 1.414(3) . ?
C6 C7 1.421(4) . ?
C7 C8 1.369(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.415(4) . ?
C8 H8 0.9500 . ?
C9 C1 1.411(4) 2_766 ?
C9 C10 1.429(4) . ?
C10 C12 1.415(4) 2_766 ?
C10 C11 1.422(4) . ?
C11 C12 1.436(3) . ?
C12 C10 1.415(4) 2_766 ?
C13 C21 1.355(4) 2_575 ?
C13 C14 1.405(4) . ?
C13 H13 0.9500 . ?
C14 C24 1.423(3) . ?
C14 C15 1.426(4) . ?
C15 C16 1.354(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.421(4) . ?
C16 H16 0.9500 . ?
C17 C23 1.414(4) . ?
C17 C18 1.419(4) . ?
C18 C19 1.360(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.417(3) . ?
C20 C21 1.424(4) . ?
C21 C13 1.355(4) 2_575 ?
C21 H21 0.9500 . ?
C22 C23 1.421(3) . ?
C22 C24 1.427(3) 2_575 ?
C23 C24 1.425(3) . ?
C24 C22 1.427(3) 2_575 ?
C25 C26 1.386(3) . ?
C25 C30 1.409(3) . ?
C25 C31 1.442(4) . ?
C26 C27 1.389(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.412(4) . ?
C27 C32 1.441(4) . ?
C28 C29 1.388(4) . ?
C28 C33 1.447(4) . ?
C29 C30 1.396(3) . ?
C29 H29 0.9500 . ?
C30 C34 1.435(4) . ?
C31 N1 1.146(3) . ?
C32 N2 1.147(3) . ?
C33 N3 1.141(3) . ?
C34 N4 1.151(3) . ?
C35 C36 1.391(3) . ?
C35 C37 1.407(3) 2_655 ?
C35 C38 1.442(3) . ?
C36 C37 1.390(3) . ?
C36 H36 0.9500 . ?
C37 C35 1.407(3) 2_655 ?
C37 C39 1.441(4) . ?
C38 N5 1.148(3) . ?
C39 N6 1.152(3) . ?
