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_4038373
_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         'C13 H8 Cl2 N P'
_chemical_formula_sum            'C13 H8 Cl2 N P'
_chemical_formula_weight         280.07
_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             2016-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9632(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.62852(12)
_cell_length_b                   13.86704(18)
_cell_length_c                   9.96682(11)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.1740
_cell_measurement_theta_min      5.1430
_cell_volume                     1189.70(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      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -61.00  34.00   0.50    1.00    --  -38.50  38.00 150.00  190
  2  \w   -109.00 -80.00   0.50    1.00    --  -38.50 -77.00  90.00   58
  3  \w   -104.00 -19.00   0.50    1.00    --  -38.50 -38.00 -30.00  170
  4  \w     52.00  79.00   0.50    1.00    --   42.75-125.00-180.00   54
  5  \w     39.00 115.00   0.50    3.00    --  111.00-125.00-120.00  152
  6  \w     81.00 108.00   0.50    3.00    --  111.00 -94.00-150.00   54
  7  \w     70.00 139.00   0.50    3.00    --  111.00 -61.00-150.00  138
  8  \w    124.00 178.00   0.50    3.00    --  111.00  45.00 -60.00  108
  9  \w    125.00 176.00   0.50    3.00    --  111.00  61.00  30.00  102
 10  \w    153.00 178.00   0.50    3.00    --  111.00  45.00 120.00   50
 11  \w     95.00 178.00   0.50    3.00    --  111.00 125.00 120.00  166
 12  \w     89.00 116.00   0.50    3.00    --  111.00  45.00 -60.00   54
 13  \w     87.00 138.00   0.50    3.00    --  111.00  45.00 120.00  102
 14  \w     55.00  99.00   0.50    3.00    --  111.00 -99.00  38.00   88
 15  \w     65.00  92.00   0.50    3.00    --  111.00 -94.00 150.00   54
 16  \w     43.00  97.00   0.50    3.00    --  111.00 -94.00  90.00  108
;
_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      0.1728896000
_diffrn_orient_matrix_UB_12      0.0015826000
_diffrn_orient_matrix_UB_13      0.0503996000
_diffrn_orient_matrix_UB_21      0.0172129000
_diffrn_orient_matrix_UB_22      -0.1053166000
_diffrn_orient_matrix_UB_23      -0.0459954000
_diffrn_orient_matrix_UB_31      0.0432591000
_diffrn_orient_matrix_UB_32      0.0352733000
_diffrn_orient_matrix_UB_33      -0.1390540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6081
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.284
_diffrn_reflns_theta_min         5.138
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.953
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.414
_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    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0232
_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^)+(0.0374P)^2^+0.3669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2374
_reflns_number_total             2471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_009.cif
_cod_data_source_block           jjw0527
_cod_database_code               4038373
_chemical_oxdiff_formula         'C52 H32 Cl8 N4 P4 '
_chemical_oxdiff_usercomment     RS150
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              64580
_shelx_hkl_checksum              8247
_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.760