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_4038368
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H16 N2 P, C F3 O3 S'
_chemical_formula_sum            'C27 H16 F3 N2 O3 P S'
_chemical_formula_weight         536.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.4693(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5520(2)
_cell_length_b                   8.75829(9)
_cell_length_c                   16.02248(19)
_cell_measurement_reflns_used    7032
_cell_measurement_temperature    99.99(17)
_cell_measurement_theta_max      76.3380
_cell_measurement_theta_min      5.0630
_cell_volume                     2259.30(5)
_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      99.99(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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    0.50    --  -38.50  38.00 150.00  190
  2  \w    -70.00  35.00   0.50    0.50    --  -38.50  77.00-120.00  210
  3  \w     20.00 115.00   0.50    0.50    --   42.75  38.00  30.00  190
  4  \w     30.00 109.00   0.50    1.50    --  111.00 -94.00  90.00  158
  5  \w     41.00 139.00   0.50    1.50    --  111.00 -61.00-180.00  196
  6  \w     36.00 135.00   0.50    1.50    --  111.00 -30.00 -60.00  198
  7  \w     87.00 178.00   0.50    1.50    --  111.00  30.00-150.00  182
  8  \w     40.00 135.00   0.50    1.50    --  111.00 -45.00  60.00  190
  9  \w     87.00 178.00   0.50    1.50    --  111.00  30.00 -30.00  182
 10  \w     40.00 135.00   0.50    1.50    --  111.00 -45.00 -90.00  190
 11  \w     83.00 178.00   0.50    1.50    --  111.00  61.00   0.00  190
 12  \w     37.00 142.00   0.50    1.50    --  111.00 -77.00  60.00  210
 13  \w     20.00 100.00   0.50    0.50    --   42.75  38.00-180.00  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      -0.0694431000
_diffrn_orient_matrix_UB_12      0.1036800000
_diffrn_orient_matrix_UB_13      0.0037789000
_diffrn_orient_matrix_UB_21      0.0153339000
_diffrn_orient_matrix_UB_22      -0.0626646000
_diffrn_orient_matrix_UB_23      0.0951941000
_diffrn_orient_matrix_UB_31      0.0640510000
_diffrn_orient_matrix_UB_32      0.1275080000
_diffrn_orient_matrix_UB_33      0.0437027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.606
_diffrn_reflns_theta_min         5.495
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.508
_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    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+2.2228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3750
_reflns_number_total             3760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_006.cif
_cod_data_source_block           jjw0544
_cod_database_code               4038368
_chemical_oxdiff_formula         'C108 H64 F12 N8 O12 P4 S4 '
_chemical_oxdiff_usercomment     RS160
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.63(3) 0.37(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
S1 \\sim C27: within 2A with sigma of 0.0005 and sigma for terminal atoms of
0.001
Uanis(C27) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              97836
_shelx_hkl_checksum              16606
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.761