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_4038378
_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         'C40 H30 N6 P, C F3 O3 S'
_chemical_formula_sum            'C41 H30 F3 N6 O3 P S'
_chemical_formula_weight         774.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.79642(10)
_cell_length_b                   19.3254(2)
_cell_length_c                   42.2670(6)
_cell_measurement_reflns_used    16182
_cell_measurement_temperature    99.99(18)
_cell_measurement_theta_max      76.5450
_cell_measurement_theta_min      4.1720
_cell_volume                     7185.15(15)
_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      99.99(18)
_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 0.990
_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 -60.00   0.50    5.00    --  -38.50 -61.00 -94.00   96
  2  \w     21.00  70.00   0.50    5.00    --   42.75  68.00-174.00   98
  3  \w     32.00  71.00   0.50   20.00    --  111.00 -98.00 171.00   78
  4  \w     48.00 138.00   0.50   20.00    --  111.00 -61.00 -94.00  180
  5  \w     54.00  95.00   0.50   20.00    --  111.00 -68.00  51.00   82
  6  \w    -87.00 -10.00   0.50    5.00    --  -38.50 125.00-150.00  154
  7  \w     69.00 107.00   0.50    5.00    --   42.75  38.00  30.00   76
  8  \w     84.00 111.00   0.50   20.00    --  111.00  61.00  60.00   54
  9  \w     71.00  99.00   0.50   20.00    --  111.00 -94.00-150.00   56
 10  \w    108.00 172.00   0.50   20.00    --  111.00 125.00 -60.00  128
 11  \w    144.00 175.00   0.50   20.00    --  111.00  61.00  60.00   62
 12  \w     59.00  89.00   0.50   20.00    --  111.00 -94.00 -90.00   60
 13  \w     40.00  94.00   0.50   20.00    --  111.00 -94.00  60.00  108
 14  \w    122.00 176.00   0.50   20.00    --  111.00 125.00   0.00  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      0.0637149000
_diffrn_orient_matrix_UB_12      -0.0518503000
_diffrn_orient_matrix_UB_13      -0.0242887000
_diffrn_orient_matrix_UB_21      -0.1189469000
_diffrn_orient_matrix_UB_22      0.0242783000
_diffrn_orient_matrix_UB_23      -0.0243410000
_diffrn_orient_matrix_UB_31      0.1117022000
_diffrn_orient_matrix_UB_32      0.0554335000
_diffrn_orient_matrix_UB_33      -0.0120965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            27926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.584
_diffrn_reflns_theta_min         4.184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.528
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       needle
_exptl_crystal_F_000             3200
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         7476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0370P)^2^+9.9231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6892
_reflns_number_total             7476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_014.cif
_cod_data_source_block           jjw0516
_cod_original_cell_volume        7185.17(15)
_cod_database_code               4038378
_chemical_oxdiff_formula         'C328 H240 F24 N48 O24 P8 S8 '
_chemical_oxdiff_usercomment     RS129
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              62177
_shelx_hkl_checksum              30640
_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 2.649
_oxdiff_exptl_absorpt_empirical_full_min 0.463