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_4038366
_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         'C14 H8 N2 P S2, C F3 O3 S, C2 H3 N'
_chemical_formula_sum            'C17 H11 F3 N3 O3 P S3'
_chemical_formula_weight         489.44
_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             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                93.2154(14)
_cell_angle_beta                 102.3339(17)
_cell_angle_gamma                90.6727(19)
_cell_formula_units_Z            2
_cell_length_a                   8.9698(2)
_cell_length_b                   9.62662(19)
_cell_length_c                   11.58620(18)
_cell_measurement_reflns_used    6204
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.2400
_cell_measurement_theta_min      3.8580
_cell_volume                     975.54(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    1.75    --   42.50  57.00 -30.00  188
  2  \w     94.00 172.00   0.50    7.00    --  111.00 125.00 -30.00  156
  3  \w    117.00 177.00   0.50    7.00    --  111.00  45.00  90.00  120
  4  \w     94.00 162.00   0.50    7.00    --  111.00 125.00  90.00  136
  5  \w     83.00 176.00   0.50    7.00    --  111.00  61.00 150.00  186
  6  \w     87.00 177.00   0.50    7.00    --  111.00  45.00  60.00  180
  7  \w     96.00 155.00   0.50    7.00    --  111.00 125.00-120.00  118
  8  \w     95.00 122.00   0.50    7.00    --  111.00  30.00-150.00   54
  9  \w    132.00 157.00   0.50    7.00    --  111.00  30.00-150.00   50
 10  \w    106.00 138.00   0.50    7.00    --  111.00 -61.00-180.00   64
 11  \w     75.00 119.00   0.50    7.00    --  111.00-125.00-150.00   88
 12  \w     70.00  97.00   0.50    7.00    --  111.00 -77.00 -90.00   54
 13  \w     63.00 119.00   0.50    7.00    --  111.00-125.00 -60.00  112
 14  \w     65.00 138.00   0.50    7.00    --  111.00 -61.00 -30.00  146
 15  \w     80.00 118.00   0.50    7.00    --  111.00-125.00 120.00   76
 16  \w     77.00 106.00   0.50    7.00    --  111.00-125.00 150.00   58
 17  \w     54.00 119.00   0.50    7.00    --  111.00 -61.00  90.00  130
 18  \w     51.00 120.00   0.50    7.00    --  111.00-125.00  30.00  138
 19  \w     43.00  70.00   0.50    7.00    --  111.00 -94.00  30.00   54
 20  \w     37.00  96.00   0.50    1.75    --   42.50-125.00  30.00  118
 21  \w     25.00  64.00   0.50    1.75    --   42.50-125.00 -90.00   78
 22  \w     37.00  99.00   0.50    7.00    --  111.00 -30.00-180.00  124
 23  \w     72.00  97.00   0.50    7.00    --  111.00 -94.00-180.00   50
 24  \w     56.00  85.00   0.50    7.00    --  111.00 -61.00-180.00   58
 25  \w    -64.00 -19.00   0.50    1.75    --  -38.50  57.00-150.00   90
 26  \w    -16.00  30.00   0.50    1.75    --  -38.50  57.00-150.00   92
 27  \w   -108.00 -15.00   0.50    1.75    --  -38.50 -57.00  60.00  186
;
_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      -0.1667638000
_diffrn_orient_matrix_UB_12      0.0206257000
_diffrn_orient_matrix_UB_13      0.0104569000
_diffrn_orient_matrix_UB_21      0.0437169000
_diffrn_orient_matrix_UB_22      0.1454214000
_diffrn_orient_matrix_UB_23      0.0612032000
_diffrn_orient_matrix_UB_31      -0.0347176000
_diffrn_orient_matrix_UB_32      0.0642906000
_diffrn_orient_matrix_UB_33      -0.1213950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.541
_diffrn_reflns_theta_min         3.912
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.767
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0667P)^2^+0.4652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3807
_reflns_number_total             4048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_007.cif
_cod_data_source_block           jjw0612
_cod_original_cell_volume        975.54(4)
_cod_database_code               4038366
_chemical_oxdiff_formula         'C34 H22 F6 N6 O6 P2 S6 '
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              10200
_shelx_hkl_checksum              98212
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.808