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_7240992
_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         'C25 H21 N9, 2(F6 P), 0.5(O)'
_chemical_formula_sum            'C25 H21 F12 N9 O0.5 P2'
_chemical_formula_weight         745.45
_chemical_name_systematic        'Methyl TPHAP'
_chemical_properties_physical    Photo-sensitive
_space_group_crystal_system      tetragonal
_space_group_IT_number           87
_space_group_name_Hall           '-I 4'
_space_group_name_H-M_alt        'I 4/m'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1313(6)
_cell_length_b                   17.1313(6)
_cell_length_c                   20.8643(6)
_cell_measurement_reflns_used    11750
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.1160
_cell_measurement_theta_min      1.7520
_cell_volume                     6123.3(4)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -110.00  70.00   0.50    4.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50    4.00    --  -20.00  45.00  90.00  360
  3  \w   -110.00  70.00   0.50    4.00    --  -20.00  45.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159053000
_diffrn_orient_matrix_UB_12      -0.0382075000
_diffrn_orient_matrix_UB_13      0.0007371000
_diffrn_orient_matrix_UB_21      0.0060908000
_diffrn_orient_matrix_UB_22      0.0015820000
_diffrn_orient_matrix_UB_23      -0.0336048000
_diffrn_orient_matrix_UB_31      0.0377401000
_diffrn_orient_matrix_UB_32      0.0158616000
_diffrn_orient_matrix_UB_33      0.0051001000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         1.538
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59080
_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            'clear light yellow'
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       prism
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.314
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.314
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.1137
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3326
_refine_ls_wR_factor_ref         0.3747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2142
_reflns_number_total             3642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00850h2.cif
_cod_data_source_block           Me3TPHAP
_cod_original_cell_volume        6123.3(5)
_cod_original_formula_sum        'C25 H21 F12 N9 O0.50 P2'
_cod_database_code               7240992
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H22N9P2F12
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H20A(0.5) H20B(0.5) H20C(0.5) P1C(0.25) F2C(0.5) F3C(0.25)
 F4C(0.25) F5C(0.5) O1(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              90749
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.639