#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:44:21 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223594 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232112.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_7232112
loop_
_publ_author_name
'Mandal, Arkalekha'
'Swain, Pravasini'
'Nath, Bhaskar'
'Sau, Sudip'
'Mal, Prasenjit'
_publ_section_title
;
 Unipolar to ambipolar semiconductivity switching in charge transfer
 cocrystals of 2,7-di-tert-butylpyrene
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              981
_journal_paper_doi               10.1039/C8CE01806E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C18 H15 N2'
_chemical_formula_weight         259.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                97.057(2)
_cell_angle_beta                 97.633(2)
_cell_angle_gamma                96.111(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9929(2)
_cell_length_b                   9.6745(3)
_cell_length_c                   10.9094(3)
_cell_measurement_reflns_used    2600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.44
_cell_measurement_theta_min      4.13
_cell_volume                     720.29(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10553
_diffrn_reflns_theta_full        67.44
_diffrn_reflns_theta_max         67.44
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1203P)²+0.0706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                2260
_reflns_number_total             2600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce01806e2.cif
_cod_data_source_block           Cocrystal1
_cod_depositor_comments
'Adding full bibliography for 7232112--7232114.cif.'
_cod_database_code               7232112
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C8 C 0.45854(15) 0.46877(12) 0.43852(11) 0.0361(3) Uani 1 1 d .
C3 C 0.38081(17) 0.32465(13) 0.41523(12) 0.0393(3) Uani 1 1 d .
C6 C 0.45204(16) 0.54892(13) 0.33829(12) 0.0392(3) Uani 1 1 d .
C13 C 0.07150(17) 0.64219(14) 0.50040(13) 0.0432(3) Uani 1 1 d .
C4 C 0.38880(17) 0.24617(13) 0.51902(13) 0.0432(3) Uani 1 1 d .
H4 H 0.3381 0.1518 0.5054 0.052 Uiso 1 1 calc R
C5 C 0.46768(18) 0.30537(13) 0.63563(13) 0.0426(3) Uani 1 1 d .
H5 H 0.4703 0.2511 0.7004 0.051 Uiso 1 1 calc R
C7 C 0.37123(18) 0.48388(14) 0.21869(13) 0.0449(4) Uani 1 1 d .
H7 H 0.3660 0.5372 0.1533 0.054 Uiso 1 1 calc R
C2 C 0.30325(19) 0.26499(13) 0.29386(13) 0.0458(4) Uani 1 1 d .
H2 H 0.2531 0.1705 0.2790 0.055 Uiso 1 1 calc R
C1 C 0.29803(18) 0.34202(14) 0.19343(13) 0.0474(4) Uani 1 1 d .
C14 C -0.02289(18) 0.55613(15) 0.38737(13) 0.0457(4) Uani 1 1 d .
H15 H -0.0369 0.5949 0.3133 0.055 Uiso 1 1 calc R
C15 C -0.09116(18) 0.42133(15) 0.38638(13) 0.0456(4) Uani 1 1 d .
H14 H -0.1519 0.3680 0.3119 0.055 Uiso 1 1 calc R
C16 C 0.14043(19) 0.78092(15) 0.50110(14) 0.0494(4) Uani 1 1 d .
N1 N 0.3106(3) 0.94388(17) 0.69847(16) 0.0840(5) Uani 1 1 d .
N2 N 0.1112(3) 0.89906(17) 0.30220(16) 0.0851(5) Uani 1 1 d .
C9 C 0.2167(2) 0.26763(17) 0.06183(14) 0.0605(4) Uani 1 1 d .
C18 C 0.1231(2) 0.84556(15) 0.39028(16) 0.0591(4) Uani 1 1 d .
C17 C 0.2345(2) 0.86981(15) 0.61158(16) 0.0581(4) Uani 1 1 d .
C12 C 0.0025(3) 0.2120(3) 0.05820(18) 0.0979(8) Uani 1 1 d .
H12A H -0.0091 0.1513 0.1208 0.147 Uiso 1 1 calc R
H12C H -0.0476 0.1605 -0.0227 0.147 Uiso 1 1 calc R
H12B H -0.0702 0.2894 0.0742 0.147 Uiso 1 1 calc R
C10 C 0.2253(4) 0.3652(2) -0.03743(17) 0.0964(8) Uani 1 1 d .
H10A H 0.1584 0.4443 -0.0159 0.145 Uiso 1 1 calc R
H10B H 0.1643 0.3154 -0.1170 0.145 Uiso 1 1 calc R
H10C H 0.3586 0.3972 -0.0420 0.145 Uiso 1 1 calc R
C11 C 0.3301(4) 0.1461(3) 0.0299(2) 0.1176(10) Uani 1 1 d .
H11A H 0.4614 0.1818 0.0238 0.176 Uiso 1 1 calc R
H11B H 0.2701 0.0929 -0.0484 0.176 Uiso 1 1 calc R
H11C H 0.3305 0.0867 0.0943 0.176 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C6 C8 C3 119.31(12) . .
C6 C8 C8 120.60(13) . 2_666
C3 C8 C8 120.09(14) . 2_666
C2 C3 C8 119.17(12) . .
C2 C3 C4 122.82(11) . .
C8 C3 C4 118.01(12) . .
C7 C6 C8 119.05(11) . .
C7 C6 C5 122.76(12) . 2_666
C8 C6 C5 118.19(12) . 2_666
C16 C13 C14 121.21(13) . .
C16 C13 C15 120.91(13) . 2_566
C14 C13 C15 117.88(12) . 2_566
C5 C4 C3 121.91(11) . .
C5 C4 H4 119.0 . .
C3 C4 H4 119.0 . .
C4 C5 C6 121.21(12) . 2_666
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 2_666 .
C1 C7 C6 122.53(12) . .
C1 C7 H7 118.7 . .
C6 C7 H7 118.7 . .
C3 C2 C1 122.32(12) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C7 C1 C2 117.60(12) . .
C7 C1 C9 123.17(13) . .
C2 C1 C9 119.21(12) . .
C15 C14 C13 121.42(13) . .
C15 C14 H15 119.3 . .
C13 C14 H15 119.3 . .
C14 C15 C13 120.70(14) . 2_566
C14 C15 H14 119.6 . .
C13 C15 H14 119.6 2_566 .
C13 C16 C18 121.81(14) . .
C13 C16 C17 122.83(13) . .
C18 C16 C17 115.36(12) . .
C11 C9 C10 109.09(18) . .
C11 C9 C12 109.56(19) . .
C10 C9 C12 107.03(16) . .
C11 C9 C1 109.37(15) . .
C10 C9 C1 112.77(13) . .
C12 C9 C1 108.97(13) . .
N2 C18 C16 178.96(17) . .
N1 C17 C16 178.26(16) . .
C9 C12 H12A 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
H12C C12 H12B 109.5 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C8 C6 1.4148(18) .
C8 C3 1.4209(18) .
C8 C8 1.421(2) 2_666
C3 C2 1.3912(19) .
C3 C4 1.4370(18) .
C6 C7 1.3944(19) .
C6 C5 1.4400(17) 2_666
C13 C16 1.376(2) .
C13 C14 1.437(2) .
C13 C15 1.443(2) 2_566
C4 C5 1.3483(18) .
C4 H4 0.9300 .
C5 C6 1.4401(17) 2_666
C5 H5 0.9300 .
C7 C1 1.3934(19) .
C7 H7 0.9300 .
C2 C1 1.397(2) .
C2 H2 0.9300 .
C1 C9 1.5313(19) .
C14 C15 1.338(2) .
C14 H15 0.9300 .
C15 C13 1.443(2) 2_566
C15 H14 0.9300 .
C16 C18 1.425(2) .
C16 C17 1.428(2) .
N1 C17 1.146(2) .
N2 C18 1.144(2) .
C9 C11 1.518(3) .
C9 C10 1.524(2) .
C9 C12 1.530(3) .
C12 H12A 0.9600 .
C12 H12C 0.9600 .
C12 H12B 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
