Pyridinium modification of a hexaazaphenalene skeleton: structure and spectroelectrochemical analysis
Deekamwong, Krittanun; Usov, Pavel M.; Ohtsu, Hiroyoshi; Kawano, Masaki; CrystEngComm  (2020) –; doi:10.1039/D0CE00850H

data_7240991
_publ_section_title
;
 Pyridinium modification of a hexaazaphenalene skeleton: structure and
 spectroelectrochemical analysis
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00850H
_journal_year                    2020
_chemical_formula_moiety         '2(F6 P), C34 H33 N9 O6, 2(C4 H10 O2)'
_chemical_formula_sum            'C42 H53 F12 N9 O10 P2'
_chemical_formula_weight         1133.87
_chemical_name_systematic        'Ethyl acetate TPHAP'
_chemical_properties_physical    Photo-sensitive
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-05 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.028(3)
_cell_angle_beta                 99.333(2)
_cell_angle_gamma                91.867(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6426(3)
_cell_length_b                   17.2337(6)
_cell_length_c                   18.5797(3)
_cell_measurement_reflns_used    6341
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.1530
_cell_measurement_theta_min      4.3350
_cell_volume                     2570.64(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -39.00   6.00   0.50   11.00    --   -1.25 -56.00 -11.00   90
  2  \w     -5.00  31.00   0.50   11.00    --   -1.25 -99.00  30.00   72
  3  \w     22.00  57.00   0.50   30.00    --   84.18 -56.00 -11.00   70
  4  \w     17.00  68.00   0.50   30.00    --   84.18 -57.00 -60.00  102
  5  \w     51.00 112.00   0.50   30.00    --   84.18-125.00 -60.00  122
  6  \w     64.00  90.00   0.50   30.00    --   84.18-125.00  60.00   52
  7  \w     48.00 105.00   0.50   30.00    --   84.18 -99.00  90.00  114
  8  \w     44.00 108.00   0.50   30.00    --   84.18-125.00  90.00  128
  9  \w     16.00 105.00   0.50   30.00    --   84.18 -99.00 -60.00  178
 10  \w     10.00  43.00   0.50   30.00    --   84.18 -37.00  30.00   66
 11  \w     10.00  44.00   0.50   30.00    --   84.18 -37.00   0.00   68
 12  \w     73.00 101.00   0.50   30.00    --   84.18  57.00 -30.00   56
 13  \w    115.00 156.00   0.50   30.00    --   84.18  57.00 -30.00   82
 14  \w     74.00 146.00   0.50   30.00    --   84.18  56.00 130.00  144
 15  \w     12.00  43.00   0.50   30.00    --   84.18 -37.00 150.00   62
 16  \w    -11.00  71.00   0.50   11.00    --   -1.25  56.00 130.00  164
 17  \w    -44.00 -16.00   0.50   30.00    --  -86.68  56.00 130.00   56
 18  \w    -39.00 -14.00   0.50   30.00    --  -86.68  37.00 150.00   50
 19  \w    -39.00 -14.00   0.50   30.00    --  -86.68  37.00 120.00   50
 20  \w    -40.00 -14.00   0.50   30.00    --  -86.68  37.00 -30.00   52
 21  \w    -39.00 -14.00   0.50   30.00    --  -86.68  37.00 -90.00   50
 22  \w    -55.00 -20.00   0.50   30.00    --  -86.68  57.00 -60.00   70
 23  \w    -64.00 -39.00   0.50   30.00    --  -86.68  57.00 -90.00   50
 24  \w    -62.00 -23.00   0.50   30.00    --  -86.68  57.00-150.00   78
 25  \w    -87.00 -61.00   0.50   30.00    --  -86.68  77.00-180.00   52
 26  \w    -90.00 -18.00   0.50   30.00    --  -86.68  77.00-150.00  144
 27  \w    -73.00 -42.00   0.50   11.00    --   -1.25 -56.00 -11.00   62
 28  \w    -10.00  33.00   0.50   11.00    --   -1.25 -99.00-150.00   86
 29  \w     11.00  43.00   0.50   30.00    --   84.18 -37.00-180.00   64
 30  \w     19.00  44.00   0.50   30.00    --   84.18-125.00 -60.00   50
 31  \w    -98.00 -73.00   0.50   30.00    --  -86.68 -56.00 -11.00   50
 32  \w   -156.00-109.00   0.50   30.00    --  -86.68 -56.00 -11.00   94
 33  \w   -160.00 -81.00   0.50   30.00    --  -86.68 -37.00  60.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0712831000
_diffrn_orient_matrix_UB_12      0.0903245000
_diffrn_orient_matrix_UB_13      0.0302039000
_diffrn_orient_matrix_UB_21      0.1370943000
_diffrn_orient_matrix_UB_22      -0.0221891000
_diffrn_orient_matrix_UB_23      0.0517186000
_diffrn_orient_matrix_UB_31      0.0950354000
_diffrn_orient_matrix_UB_32      -0.0191377000
_diffrn_orient_matrix_UB_33      -0.0661208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23324
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        61.168
_diffrn_reflns_theta_max         61.168
_diffrn_reflns_theta_min         4.321
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       plate
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         7882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1012
_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/[\s^2^(Fo^2^)+(0.1269P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.2018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5098
_reflns_number_total             7882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00850h2.cif
_cod_data_source_block           Ethylacetate_TPHAP
_cod_database_code               7240991
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H22 N9 O6 P F6'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C42B)=Sof(H42C)=Sof(H42D)=Sof(C43B)=Sof(H43D)=Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(C42A)=Sof(H42A)=Sof(H42B)=Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C44(H44A,H44B), C32(H32A,H32B), C48(H48A,H48B), C3D(H3DA,
 H3DB), C36(H36A,H36B), C3C(H3CA,H3CB), C4D(H4DA,H4DB), C4C(H4CA,H4CB),
 C42A(H42A,H42B), C42B(H42C,H42D)
3.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C22(H22), C25(H25), C3(H3), C31(H31), C2(H2), C21(H21), C24(H24),
 C5(H5), C6(H6), C30(H30), C27(H27)
3.c Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C6D(H6DA,H6DB,H6DC), C37(H37A,H37B,H37C), C6C(H6CA,H6CB,
 H6CC), C1D(H1DA,H1DB,H1DC), C1C(H1CA,H1CB,H1CC), C43A(H43A,H43B,H43C),
 C43B(H43D,H43E,H43F)
;
_shelx_res_checksum              20610
_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 2.634
_oxdiff_exptl_absorpt_empirical_full_min 0.450