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_4038374
_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         'C9 H6 Cl2 N P'
_chemical_formula_sum            'C9 H6 Cl2 N P'
_chemical_formula_weight         230.02
_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             2017-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.657(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4333(5)
_cell_length_b                   5.84986(19)
_cell_length_c                   14.1072(5)
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.0080
_cell_measurement_theta_min      4.0790
_cell_volume                     966.26(7)
_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 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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      8.00 118.00   0.50    0.50    --   42.75  19.00 150.00  220
  2  \w     61.00 111.00   0.50    2.00    --  111.00 -77.00  60.00  100
  3  \w     75.00 129.00   0.50    2.00    --  111.00 -45.00 -30.00  108
  4  \w    114.00 160.00   0.50    2.00    --  111.00  30.00 -60.00   92
  5  \w     95.00 177.00   0.50    2.00    --  111.00  30.00-150.00  164
  6  \w    129.00 164.00   0.50    2.00    --  111.00 125.00   0.00   70
  7  \w     43.00 136.00   0.50    2.00    --  111.00 -61.00  90.00  186
  8  \w     45.00 135.00   0.50    2.00    --  111.00 -77.00 -60.00  180
  9  \w     66.00  91.00   0.50    2.00    --  111.00 -94.00-180.00   50
 10  \w     39.00 114.00   0.50    2.00    --  111.00-125.00 -90.00  150
 11  \w     35.00  67.00   0.50    0.50    --   42.75-140.00   5.00   64
 12  \w   -103.00 -16.00   0.50    0.50    --  -38.50 -38.00-180.00  174
;
_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      -0.0948861000
_diffrn_orient_matrix_UB_12      -0.0847330000
_diffrn_orient_matrix_UB_13      -0.0952345000
_diffrn_orient_matrix_UB_21      0.0539103000
_diffrn_orient_matrix_UB_22      0.1363089000
_diffrn_orient_matrix_UB_23      -0.0660399000
_diffrn_orient_matrix_UB_31      0.0735234000
_diffrn_orient_matrix_UB_32      -0.2087880000
_diffrn_orient_matrix_UB_33      -0.0045178000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.808
_diffrn_reflns_theta_min         4.108
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.181
_exptl_absorpt_correction_T_max  0.114
_exptl_absorpt_correction_T_min  0.012
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.139
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0625
_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^)+(0.1263P)^2^+0.1068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             2004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_008.cif
_cod_data_source_block           jjw573
_cod_original_cell_volume        966.27(6)
_cod_database_code               4038374
_chemical_oxdiff_formula         'C36 H24 Cl8 N4 P4 '
_reflns_odcompleteness_completeness 100.00
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
;
_shelx_res_checksum              83910
_shelx_hkl_checksum              27107
_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 3.075
_oxdiff_exptl_absorpt_empirical_full_min 0.367