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_4038367
_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_absolute_configuration ad
_chemical_formula_moiety         'C F3 O3 S, C10 H8 F4 N2 P'
_chemical_formula_sum            'C11 H8 F7 N2 O3 P S'
_chemical_formula_weight         412.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.5932(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.73091(8)
_cell_length_b                   7.86576(5)
_cell_length_c                   11.09899(9)
_cell_measurement_reflns_used    8261
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      76.3870
_cell_measurement_theta_min      4.2720
_cell_volume                     713.521(11)
_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      air
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -65.00  32.00   0.50    2.00    --  -38.50  57.00 -30.00  194
  2  \w     16.00 113.00   0.50    2.00    --   42.75  57.00  60.00  194
  3  \w    -30.00  65.00   0.50    2.00    --   42.75 -38.00 120.00  190
  4  \w    -27.00  69.00   0.50    2.00    --   42.75 -57.00  60.00  192
  5  \w     11.00 117.00   0.50    2.00    --   42.75  77.00  90.00  212
  6  \w     11.00 117.00   0.50    2.00    --   42.75  77.00   0.00  212
  7  \w     23.00  98.00   0.50    2.00    --   42.75-125.00  60.00  150
  8  \w     11.00 117.00   0.50    2.00    --   42.75  77.00 -90.00  212
  9  \w     11.00 117.00   0.50    2.00    --   42.75  77.00-180.00  212
 10  \w     23.00  98.00   0.50    2.00    --   42.75-125.00-120.00  150
 11  \w     80.00 178.00   0.50    4.00    --  111.00  77.00 -60.00  196
 12  \w     80.00 178.00   0.50    4.00    --  111.00  77.00 120.00  196
 13  \w     39.00 121.00   0.50    4.00    --  111.00-125.00-180.00  164
 14  \w     83.00 178.00   0.50    4.00    --  111.00  61.00-120.00  190
 15  \w     80.00 178.00   0.50    4.00    --  111.00  77.00-180.00  196
 16  \w     80.00 178.00   0.50    4.00    --  111.00  77.00 -30.00  196
 17  \w     37.00 142.00   0.50    4.00    --  111.00 -77.00  60.00  210
 18  \w     80.00 178.00   0.50    4.00    --  111.00  77.00 -90.00  196
 19  \w     30.00 109.00   0.50    4.00    --  111.00 -94.00  30.00  158
 20  \w     39.00 121.00   0.50    4.00    --  111.00-125.00 -60.00  164
 21  \w     83.00 178.00   0.50    4.00    --  111.00  61.00  60.00  190
 22  \w     80.00 178.00   0.50    4.00    --  111.00  77.00  90.00  196
 23  \w     83.00 178.00   0.50    4.00    --  111.00  61.00 -90.00  190
 24  \w     83.00 178.00   0.50    4.00    --  111.00  61.00 -60.00  190
 25  \w     83.00 178.00   0.50    4.00    --  111.00  61.00   0.00  190
 26  \w     83.00 178.00   0.50    4.00    --  111.00  61.00 120.00  190
 27  \w     83.00 178.00   0.50    4.00    --  111.00  61.00 150.00  190
 28  \w     83.00 121.00   0.50    4.00    --  111.00  61.00-150.00   76
;
_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      -0.0601892000
_diffrn_orient_matrix_UB_12      0.1796568000
_diffrn_orient_matrix_UB_13      0.0163878000
_diffrn_orient_matrix_UB_21      0.0880941000
_diffrn_orient_matrix_UB_22      -0.0129596000
_diffrn_orient_matrix_UB_23      0.1467552000
_diffrn_orient_matrix_UB_31      0.1554056000
_diffrn_orient_matrix_UB_32      0.0768984000
_diffrn_orient_matrix_UB_33      -0.0135333000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11042
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.516
_diffrn_reflns_theta_min         5.587
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1318 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0230
_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^)+(0.0451P)^2^+0.2022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                2814
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_004.cif
_cod_data_source_block           jjw0395
_cod_original_cell_volume        713.521(10)
_cod_database_code               4038367
_chemical_oxdiff_formula         C11H8F7N2O3PS
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C2(H2), C7(H7), C10(H10), C3(H3), C9(H9), C4(H4)
;
_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 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.917