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_4038365
_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         'C10 H8 Cl2 N2 P, C F3 O3 S'
_chemical_formula_sum            'C11 H8 Cl2 F3 N2 O3 P S'
_chemical_formula_weight         407.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.479(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7884(5)
_cell_length_b                   5.86021(18)
_cell_length_c                   21.1423(9)
_cell_measurement_reflns_used    8921
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      76.2980
_cell_measurement_theta_min      3.6140
_cell_volume                     1511.30(10)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_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 0.996
_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   -108.00 -12.00   0.50    6.00    --  -38.50 -57.00-120.00  192
  2  \w   -109.00 -16.00   0.50    6.00    --  -38.50 -38.00 120.00  186
  3  \w    -59.00  31.00   0.50    6.00    --  -38.50  57.00  30.00  180
  4  \w      6.00  75.00   0.50    6.00    --   42.75 -99.00  90.00  138
  5  \w     71.00  97.00   0.50    6.00    --   42.75-125.00-180.00   52
  6  \w    122.00 148.00   0.50   24.00    --  111.00 125.00 -60.00   52
  7  \w     93.00 120.00   0.50   24.00    --  111.00-125.00 120.00   54
  8  \w     60.00 115.00   0.50   24.00    --  111.00-125.00 -60.00  110
  9  \w    136.00 162.00   0.50   24.00    --  111.00  45.00   0.00   52
 10  \w     91.00 117.00   0.50   24.00    --  111.00  45.00   0.00   52
 11  \w     44.00 121.00   0.50   24.00    --  111.00-125.00   0.00  154
 12  \w     37.00 136.00   0.50   24.00    --  111.00 -77.00  90.00  198
 13  \w     83.00 139.00   0.50   24.00    --  111.00 -61.00 -90.00  112
 14  \w     98.00 174.00   0.50   24.00    --  111.00  45.00 120.00  152
 15  \w     44.00  92.00   0.50   24.00    --  111.00 -94.00 -30.00   96
 16  \w     51.00  81.00   0.50   24.00    --  111.00-125.00-150.00   60
 17  \w    107.00 178.00   0.50   24.00    --  111.00  45.00  30.00  142
 18  \w     37.00 109.00   0.50   24.00    --  111.00 -94.00  60.00  144
 19  \w     96.00 121.00   0.50   24.00    --  111.00-125.00-150.00   50
 20  \w     42.00  95.00   0.50   24.00    --  111.00-125.00 -30.00  106
 21  \w     88.00 117.00   0.50   24.00    --  111.00-125.00  60.00   58
 22  \w     45.00  83.00   0.50   24.00    --  111.00-125.00 120.00   76
 23  \w     53.00 108.00   0.50   24.00    --  111.00-125.00 -90.00  110
 24  \w     90.00 177.00   0.50   24.00    --  111.00  30.00  90.00  174
 25  \w     48.00  82.00   0.50   24.00    --  111.00 -94.00-150.00   68
 26  \w    116.00 144.00   0.50   24.00    --  111.00 125.00  30.00   56
 27  \w     36.00  67.00   0.50   24.00    --  111.00 -30.00 150.00   62
 28  \w    109.00 155.00   0.50   24.00    --  111.00 125.00-120.00   92
 29  \w     83.00 163.00   0.50   24.00    --  111.00  61.00 150.00  160
;
_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      -0.1049097000
_diffrn_orient_matrix_UB_12      0.0375404000
_diffrn_orient_matrix_UB_13      0.0201598000
_diffrn_orient_matrix_UB_21      -0.0365471000
_diffrn_orient_matrix_UB_22      0.1880170000
_diffrn_orient_matrix_UB_23      -0.0529674000
_diffrn_orient_matrix_UB_31      -0.0602569000
_diffrn_orient_matrix_UB_32      -0.1797097000
_diffrn_orient_matrix_UB_33      -0.0512206000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14505
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_min         3.624
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.637
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.460
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0740P)^2^+0.6630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3283
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_002.cif
_cod_data_source_block           jjw0548
_cod_original_cell_volume        1511.30(11)
_cod_database_code               4038365
_chemical_oxdiff_formula         C11H8Cl2F3N2O3PS
_chemical_oxdiff_usercomment     Dichlorphosphol
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.55
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4042(13) 0.5958(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10)
;
_shelx_res_checksum              72481
_shelx_hkl_checksum              14460
_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 1.852
_oxdiff_exptl_absorpt_empirical_full_min 0.692