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_4038364
_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, C20 H22 N6 P'
_chemical_formula_sum            'C21 H22 F3 N6 O3 P S'
_chemical_formula_weight         526.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2016-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.3951(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.34132(11)
_cell_length_b                   11.57043(8)
_cell_length_c                   16.78264(15)
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3530
_cell_measurement_theta_min      3.8080
_cell_volume                     2395.26(4)
_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      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 0.989
_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    -57.00  19.00   0.50    0.50    --  -38.50  38.00  30.00  152
  2  \w    -28.00  34.00   0.50    0.50    --  -38.50  38.00-120.00  124
  3  \w    -36.00   6.00   0.50    0.50    --   42.75   0.00-120.00   84
  4  \w     41.00  72.00   0.50    2.00    --  111.00 -61.00-120.00   62
  5  \w     91.00 139.00   0.50    2.00    --  111.00 -61.00-120.00   96
  6  \w     96.00 178.00   0.50    2.00    --  111.00  45.00 -60.00  164
  7  \w    141.00 170.00   0.50    2.00    --  111.00 125.00 -30.00   58
  8  \w    109.00 177.00   0.50    2.00    --  111.00  61.00 -30.00  136
  9  \w    112.00 171.00   0.50    2.00    --  111.00  30.00  60.00  118
 10  \w    103.00 174.00   0.50    2.00    --  111.00 122.00 147.00  142
 11  \w     60.00 101.00   0.50    2.00    --  111.00 -94.00 150.00   82
 12  \w     91.00 117.00   0.50    2.00    --  111.00-122.00  66.00   52
 13  \w     86.00 112.00   0.50    2.00    --  111.00-125.00  30.00   52
 14  \w     53.00 117.00   0.50    2.00    --  111.00-125.00 150.00  128
 15  \w     28.00  89.00   0.50    0.50    --   42.75-126.00 158.00  122
 16  \w     30.00  59.00   0.50    2.00    --  111.00 -94.00 -30.00   58
 17  \w     42.00  98.00   0.50    2.00    --  111.00 -94.00-120.00  112
;
_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      -0.0562991000
_diffrn_orient_matrix_UB_12      -0.0394731000
_diffrn_orient_matrix_UB_13      -0.0943750000
_diffrn_orient_matrix_UB_21      -0.0055980000
_diffrn_orient_matrix_UB_22      0.1265616000
_diffrn_orient_matrix_UB_23      -0.0301356000
_diffrn_orient_matrix_UB_31      0.1112137000
_diffrn_orient_matrix_UB_32      -0.0133914000
_diffrn_orient_matrix_UB_33      -0.0068273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.589
_diffrn_reflns_theta_min         3.583
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86857
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         4986
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0439P)^2^+0.8637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4836
_reflns_number_total             4986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_013.cif
_cod_data_source_block           jjw0440
_cod_database_code               4038364
_chemical_oxdiff_formula         C21H22F3N6O3PS
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
F3B \\sim F1B \\sim F2B \\sim C21B \\sim F1A \\sim C21A \\sim F2A \\sim F3A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
2. Others
 Sof(F3B)=Sof(F1B)=Sof(F2B)=Sof(C21B)=1-FVAR(1)
 Sof(F1A)=Sof(C21A)=Sof(F2A)=Sof(F3A)=FVAR(1)
;
_shelx_res_checksum              59702
_shelx_hkl_checksum              84766
_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.865