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_4038372
_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         'C7 H4 Cl2 N P S'
_chemical_formula_sum            'C7 H4 Cl2 N P S'
_chemical_formula_weight         236.04
_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             2017-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.2912(19)
_cell_angle_beta                 107.150(2)
_cell_angle_gamma                108.239(2)
_cell_formula_units_Z            2
_cell_length_a                   6.71538(17)
_cell_length_b                   6.98592(18)
_cell_length_c                   10.6276(2)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3340
_cell_measurement_theta_min      4.3590
_cell_volume                     448.83(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.981
_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    -58.00  28.00   0.50    0.50    --  -38.50  57.00   0.00  172
  2  \w    -29.00  -2.00   0.50    0.50    --  -38.50 125.00-150.00   54
  3  \w    -68.00 -35.00   0.50    0.50    --  -38.50 125.00-150.00   66
  4  \w     16.00 113.00   0.50    0.50    --   42.50  57.00-150.00  194
  5  \w    141.00 176.00   0.50    2.00    --  111.00  61.00-180.00   70
  6  \w    113.00 171.00   0.50    2.00    --  111.00  15.00-180.00  116
  7  \w    104.00 133.00   0.50    2.00    --  111.00 -77.00-150.00   58
  8  \w    101.00 133.00   0.50    2.00    --  111.00 -45.00-150.00   64
  9  \w     89.00 177.00   0.50    2.00    --  111.00  30.00-120.00  176
 10  \w     85.00 112.00   0.50    2.00    --  111.00  61.00-180.00   54
 11  \w     66.00  92.00   0.50    2.00    --  111.00  15.00-180.00   52
 12  \w     41.00 100.00   0.50    2.00    --  111.00 -45.00-150.00  118
 13  \w     79.00 106.00   0.50    2.00    --  111.00 -94.00-180.00   54
 14  \w     84.00 111.00   0.50    2.00    --  111.00-125.00-180.00   54
 15  \w     53.00  81.00   0.50    2.00    --  111.00 -77.00-150.00   56
 16  \w     41.00  66.00   0.50    2.00    --  111.00-125.00-180.00   50
 17  \w     39.00  78.00   0.50    2.00    --  111.00 -77.00-180.00   78
 18  \w     47.00 121.00   0.50    2.00    --  111.00-125.00 -60.00  148
 19  \w     43.00 139.00   0.50    2.00    --  111.00 -61.00  30.00  192
 20  \w    153.00 178.00   0.50    2.00    --  111.00  15.00 120.00   50
 21  \w    140.00 172.00   0.50    2.00    --  111.00  45.00  90.00   64
 22  \w    109.00 136.00   0.50    2.00    --  111.00  45.00  90.00   54
 23  \w     76.00 101.00   0.50    2.00    --  111.00  15.00 120.00   50
 24  \w     32.00 105.00   0.50    2.00    --  111.00 -94.00  30.00  146
 25  \w     46.00 102.00   0.50    2.00    --  111.00-125.00  30.00  112
 26  \w    -60.00  33.00   0.50    0.50    --  -38.50  77.00  90.00  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      -0.0114612000
_diffrn_orient_matrix_UB_12      -0.0805301000
_diffrn_orient_matrix_UB_13      -0.1390097000
_diffrn_orient_matrix_UB_21      -0.1743750000
_diffrn_orient_matrix_UB_22      0.0993140000
_diffrn_orient_matrix_UB_23      -0.0637334000
_diffrn_orient_matrix_UB_31      0.1853860000
_diffrn_orient_matrix_UB_32      0.1960624000
_diffrn_orient_matrix_UB_33      -0.0017118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.555
_diffrn_reflns_theta_min         4.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0223
_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^)+(0.0375P)^2^+0.1374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1796
_reflns_number_total             1850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_010.cif
_cod_data_source_block           jjw0611
_cod_database_code               4038372
_chemical_oxdiff_formula         'C14 H8 Cl4 N2 P2 S2 '
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              76849
_shelx_hkl_checksum              38590
_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 1.863
_oxdiff_exptl_absorpt_empirical_full_min 0.777