#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:44:21 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223594 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232114.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_7232114
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_moiety         'C24 H26, C10 H2 N4'
_chemical_formula_sum            'C34 H28 N4'
_chemical_formula_weight         492.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_symmetry_space_group_name_Hall  '-I 2y'
_symmetry_space_group_name_H-M   'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-01-21
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.087(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.3925(6)
_cell_length_b                   6.8374(3)
_cell_length_c                   12.8802(5)
_cell_measurement_reflns_used    2825
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      76.4970
_cell_measurement_theta_min      4.5960
_cell_volume                     1353.61(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  28.00   0.50    0.50    --  -38.50  38.00-174.00  140
  2  ω   -105.00 -35.00   0.50    0.50    --  -38.50 -38.00  29.00  140
  3  ω     46.00 116.00   0.50    0.50    --   49.31  38.00-174.00  140
  4  ω    -17.00  53.00   0.50    0.50    --   49.31 -38.00  29.00  140
  5  ω     40.00 110.00   0.50    2.50    --  106.38 -38.00  29.00  140
  6  ω    103.00 173.00   0.50    2.50    --  106.38  38.00-174.00  140
  7  ω    -17.00  53.00   0.50    0.50    --   49.31 -37.00 -90.00  140
  8  ω     46.00 116.00   0.50    0.50    --   49.31  37.00-120.00  140
  9  ω     44.00 120.00   0.50    2.50    --  106.38 -61.00 120.00  152
 10  ω     42.00 130.00   0.50    2.50    --  106.38 -77.00 -60.00  176
 11  ω    102.00 171.00   0.50    2.50    --  106.38  45.00 150.00  138
 12  ω     94.00 171.00   0.50    2.50    --  106.38 125.00  60.00  154
 13  ω    102.00 171.00   0.50    2.50    --  106.38  45.00-150.00  138
 14  ω    102.00 171.00   0.50    2.50    --  106.38  45.00  60.00  138
 15  ω     38.00 109.00   0.50    2.50    --  106.38 -94.00-120.00  142
 16  ω     38.00 110.00   0.50    2.50    --  106.38 -30.00-120.00  144
 17  ω     38.00 112.00   0.50    0.50    --   49.31  57.00  90.00  148
 18  ω     26.00  51.00   0.50    0.50    --   49.31  77.00 -90.00   50
 19  ω     26.00 114.00   0.50    0.50    --   49.31  77.00 -30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304464000
_diffrn_orient_matrix_UB_12      0.0345613000
_diffrn_orient_matrix_UB_13      0.1105082000
_diffrn_orient_matrix_UB_21      0.0833922000
_diffrn_orient_matrix_UB_22      -0.0987642000
_diffrn_orient_matrix_UB_23      0.0460038000
_diffrn_orient_matrix_UB_31      0.0465833000
_diffrn_orient_matrix_UB_32      0.1995311000
_diffrn_orient_matrix_UB_33      0.0037349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        76.97
_diffrn_reflns_theta_max         76.97
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0460
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                1184
_reflns_number_total             1518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce01806e2.cif
_cod_data_source_block           Cocrystal2
_cod_depositor_comments
'Adding full bibliography for 7232112--7232114.cif.'
_cod_database_code               7232114
_chemical_oxdiff_formula         'C30 H20 N4 '
_diffrn_oxdiff_ac3_digest_frames
;
015e1e73e4907bc1a8e5080cf66833bedf00038997e
;
_diffrn_oxdiff_ac3_digest_hkl
;
01b1273b102b56eb642bdb6dca03ab4092d247
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.306
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 '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_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C5 C 0.45362(10) 0.5000 0.49831(12) 0.0403(4) Uani 1 d 2 S T P
C6 C 0.40565(11) 0.5000 0.40146(13) 0.0441(4) Uani 1 d 2 S T P
C4 C 0.40900(11) 0.5000 0.59167(13) 0.0438(4) Uani 1 d 2 S T P
C8 C 0.54062(12) 0.5000 0.31126(14) 0.0504(5) Uani 1 d 2 S T P
C7 C 0.45257(12) 0.5000 0.30791(14) 0.0502(5) Uani 1 d 2 S T P
C1 C 0.31461(12) 0.5000 0.40003(15) 0.0508(5) Uani 1 d 2 S T P
C3 C 0.31811(12) 0.5000 0.58572(15) 0.0507(5) Uani 1 d 2 S T P
N1 N 0.26078(17) 0.0000 0.36777(17) 0.0843(6) Uani 1 d 2 S T P
C2 C 0.26988(11) 0.5000 0.49099(15) 0.0526(5) Uani 1 d 2 S T P
C15 C 0.57051(14) 0.0000 0.43724(14) 0.0553(5) Uani 1 d 2 S T P
C12 C 0.48726(15) 0.0000 0.39242(15) 0.0574(6) Uani 1 d 2 S T P
N2 N 0.70054(16) 0.0000 0.31928(16) 0.0862(7) Uani 1 d 2 S T P
C13 C 0.41591(14) 0.0000 0.45422(14) 0.0558(5) Uani 1 d 2 S T P
C16 C 0.64348(15) 0.0000 0.37205(16) 0.0641(6) Uani 1 d 2 S T P
C9 C 0.16976(12) 0.5000 0.49085(17) 0.0610(6) Uani 1 d 2 S T P
C14 C 0.32922(17) 0.0000 0.40682(16) 0.0642(6) Uani 1 d 2 S T P
C11 C 0.13985(11) 0.6829(3) 0.54745(17) 0.0776(6) Uani 1 d 1 . . .
C10 C 0.12850(16) 0.5000 0.3800(2) 0.0818(8) Uani 1 d 2 S T P
H3 H 0.2930(15) 0.5000 0.650(2) 0.061(6) Uiso 1 d 2 S T P
H7 H 0.4185(14) 0.5000 0.2405(19) 0.057(6) Uiso 1 d 2 S T P
H1 H 0.2814(15) 0.5000 0.3331(19) 0.058(6) Uiso 1 d 2 S T P
H11A H 0.0747(13) 0.685(3) 0.5480(14) 0.084(6) Uiso 1 d 1 . . .
H12 H 0.4772(15) 0.0000 0.317(2) 0.067(6) Uiso 1 d 2 S T P
H11B H 0.1565(14) 0.806(4) 0.5098(18) 0.108(7) Uiso 1 d 1 . . .
H11C H 0.1665(15) 0.687(3) 0.6225(18) 0.100(6) Uiso 1 d 1 . . .
H8 H 0.5724(16) 0.5000 0.247(2) 0.069(6) Uiso 1 d 2 S T P
H10A H 0.1456(13) 0.375(3) 0.3449(16) 0.085(5) Uiso 1 d 1 . . .
H10B H 0.065(2) 0.5000 0.383(2) 0.099(9) Uiso 1 d 2 S T P
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 C5 C5 120.06(18) . 5_666
C6 C5 C4 119.64(16) . .
C4 C5 C5 120.30(19) . 5_666
C5 C6 C7 118.49(16) . .
C1 C6 C5 119.07(16) . .
C1 C6 C7 122.44(17) . .
C5 C4 C8 118.40(16) . 5_666
C3 C4 C5 118.90(16) . .
C3 C4 C8 122.70(16) . 5_666
C4 C8 H8 117.5(14) 5_666 .
C7 C8 C4 121.39(17) . 5_666
C7 C8 H8 121.2(14) . .
C6 C7 H7 118.0(13) . .
C8 C7 C6 121.37(17) . .
C8 C7 H7 120.7(13) . .
C6 C1 H1 119.1(13) . .
C2 C1 C6 121.97(18) . .
C2 C1 H1 118.9(13) . .
C4 C3 H3 114.4(15) . .
C2 C3 C4 122.19(17) . .
C2 C3 H3 123.4(15) . .
C1 C2 C3 118.24(17) . .
C1 C2 C9 122.65(17) . .
C3 C2 C9 119.11(17) . .
C12 C15 C13 120.22(19) . 5_656
C12 C15 C16 119.59(18) . .
C13 C15 C16 120.2(2) 5_656 .
C15 C12 C13 120.39(18) . .
C15 C12 H12 120.7(14) . .
C13 C12 H12 118.9(14) . .
C15 C13 C14 120.56(19) 5_656 .
C12 C13 C15 119.4(2) . 5_656
C12 C13 C14 120.05(17) . .
N2 C16 C15 179.1(2) . .
C11 C9 C2 109.02(12) 6_565 .
C11 C9 C2 109.02(12) . .
C11 C9 C11 109.6(2) . 6_565
C11 C9 C10 108.89(13) . .
C11 C9 C10 108.89(13) 6_565 .
C10 C9 C2 111.44(17) . .
N1 C14 C13 179.0(2) . .
C9 C11 H11A 109.8(11) . .
C9 C11 H11B 111.1(13) . .
C9 C11 H11C 110.9(12) . .
H11A C11 H11B 105.9(16) . .
H11A C11 H11C 109.9(17) . .
H11B C11 H11C 109.1(18) . .
C9 C10 H10A 108.2(11) . .
C9 C10 H10B 109.4(19) . .
H10A C10 H10B 107.4(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C5 C5 1.426(3) 5_666
C5 C6 1.415(3) .
C5 C4 1.417(2) .
C6 C7 1.438(2) .
C6 C1 1.400(3) .
C4 C8 1.435(3) 5_666
C4 C3 1.397(2) .
C8 C4 1.435(3) 5_666
C8 C7 1.354(3) .
C8 H8 0.98(3) .
C7 H7 0.99(2) .
C1 C2 1.390(3) .
C1 H1 0.98(2) .
C3 C2 1.394(3) .
C3 H3 0.93(3) .
N1 C14 1.143(3) .
C2 C9 1.541(3) .
C15 C12 1.377(3) .
C15 C13 1.402(3) 5_656
C15 C16 1.438(3) .
C12 C13 1.391(3) .
C12 H12 0.98(2) .
N2 C16 1.139(3) .
C13 C15 1.403(3) 5_656
C13 C14 1.437(3) .
C9 C11 1.531(2) .
C9 C11 1.531(2) 6_565
C9 C10 1.531(3) .
C11 H11A 1.00(2) .
C11 H11B 1.01(2) .
C11 H11C 1.03(2) .
C10 H10A 1.01(2) .
C10 H10B 0.98(3) .
