Toward N,P-Doped π-Extended PAHs: A One-Pot Synthesis to Diannulated 1,4,2-Diazaphospholium Triflate Salts.
Schoemaker, Robin; Schwedtmann, Kai; Hennersdorf, Felix; Bauzá, Antonio; Frontera, Antonio; Weigand, Jan J.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00577

data_4038370
_publ_section_title
;
 Toward N,P-Doped \p-Extended PAHs: A One-Pot Synthesis to Diannulated
 1,4,2-Diazaphospholium Triflate Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00577
_journal_year                    2020
_chemical_formula_moiety         'C F3 O3 S, C18 H12 N2 P, C2 H3 N'
_chemical_formula_sum            'C21 H15 F3 N3 O3 P S'
_chemical_formula_weight         477.39
_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   difmap
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                116.376(3)
_cell_angle_beta                 101.678(3)
_cell_angle_gamma                96.308(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0876(3)
_cell_length_b                   12.8437(4)
_cell_length_c                   13.0350(4)
_cell_measurement_reflns_used    4806
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0080
_cell_measurement_theta_min      3.9040
_cell_volume                     1013.70(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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     18.00 112.00   0.50    1.00    --   42.50  57.00 -60.00  188
  2  \w     66.00 125.00   0.50    3.00    --  111.00  15.00  30.00  118
  3  \w    130.00 161.00   0.50    3.00    --  111.00  15.00  30.00   62
  4  \w    122.00 155.00   0.50    3.00    --  111.00  77.00 -60.00   66
  5  \w    153.00 178.00   0.50    3.00    --  111.00  45.00-150.00   50
  6  \w     99.00 152.00   0.50    3.00    --  111.00  45.00-180.00  106
  7  \w     95.00 161.00   0.50    3.00    --  111.00 125.00-120.00  132
  8  \w     94.00 123.00   0.50    3.00    --  111.00 125.00-180.00   58
  9  \w     87.00 119.00   0.50    3.00    --  111.00  77.00 -60.00   64
 10  \w     88.00 139.00   0.50    3.00    --  111.00  45.00-150.00  102
 11  \w     92.00 135.00   0.50    3.00    --  111.00 -45.00 -30.00   86
 12  \w     82.00 109.00   0.50    3.00    --  111.00 -94.00  60.00   54
 13  \w     86.00 121.00   0.50    3.00    --  111.00-125.00 120.00   70
 14  \w     99.00 138.00   0.50    3.00    --  111.00 -77.00 150.00   78
 15  \w     70.00 134.00   0.50    3.00    --  111.00 -30.00 150.00  128
 16  \w     65.00 108.00   0.50    3.00    --  111.00 -94.00   0.00   86
 17  \w     92.00 121.00   0.50    3.00    --  111.00-125.00 -30.00   58
 18  \w     91.00 120.00   0.50    3.00    --  111.00-125.00-120.00   58
 19  \w     96.00 126.00   0.50    3.00    --  111.00 -77.00-150.00   60
 20  \w     84.00 120.00   0.50    3.00    --  111.00-125.00-180.00   72
 21  \w     45.00  80.00   0.50    3.00    --  111.00-125.00 -30.00   70
 22  \w     32.00  61.00   0.50    3.00    --  111.00 -94.00   0.00   58
 23  \w     31.00  81.00   0.50    3.00    --  111.00 -94.00  60.00  100
 24  \w     40.00  72.00   0.50    3.00    --  111.00 -45.00 -30.00   64
 25  \w     38.00  80.00   0.50    3.00    --  111.00 -77.00-150.00   84
 26  \w     40.00  71.00   0.50    3.00    --  111.00-125.00-180.00   62
 27  \w    -61.00  28.00   0.50    1.00    --  -38.50  38.00-180.00  178
 28  \w    -37.00  -4.00   0.50    1.00    --  -38.50 125.00   0.00   66
 29  \w    138.00 177.00   0.50    3.00    --  111.00 125.00  90.00   78
 30  \w     38.00  91.00   0.50    3.00    --  111.00 -77.00 150.00  106
 31  \w     13.00  67.00   0.50    1.00    --   42.50 -57.00 150.00  108
 32  \w    -93.00 -58.00   0.50    1.00    --  -38.50 125.00   0.00   70
 33  \w   -110.00 -16.00   0.50    1.00    --  -38.50 -38.00   0.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206057000
_diffrn_orient_matrix_UB_12      -0.1098575000
_diffrn_orient_matrix_UB_13      0.0170962000
_diffrn_orient_matrix_UB_21      0.2118158000
_diffrn_orient_matrix_UB_22      0.0128954000
_diffrn_orient_matrix_UB_23      -0.0123012000
_diffrn_orient_matrix_UB_31      0.0816562000
_diffrn_orient_matrix_UB_32      0.0816733000
_diffrn_orient_matrix_UB_33      0.1358829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.658
_diffrn_reflns_theta_min         3.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.3423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3959
_reflns_number_total             4208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_005.cif
_cod_data_source_block           jjw0478
_cod_database_code               4038370
_chemical_oxdiff_formula         'C42 H30 F6 N6 O6 P2 S2 '
_chemical_oxdiff_usercomment     MeCN/Et2O
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              36369
_shelx_hkl_checksum              65970
_shelx_shelxl_version_number     2014/7
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.746