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_4038376
_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         'C32 H46 N6 P, C F3 O3 S, C4 H10 O'
_chemical_formula_sum            'C37 H56 F3 N6 O4 P S'
_chemical_formula_weight         768.90
_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   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                 99.5180(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.32700(13)
_cell_length_b                   12.54811(10)
_cell_length_c                   19.52034(14)
_cell_measurement_reflns_used    16895
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.4300
_cell_measurement_theta_min      4.1910
_cell_volume                     4185.71(6)
_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 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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     22.00  55.00   0.50    1.25    --   42.50  57.00 -60.00   66
  2  \w     88.00 175.00   0.50    5.00    --  111.00  45.00-120.00  174
  3  \w    143.00 176.00   0.50    5.00    --  111.00  45.00 -60.00   66
  4  \w    110.00 136.00   0.50    5.00    --  111.00 -61.00   0.00   52
  5  \w     59.00  86.00   0.50    5.00    --  111.00 -94.00 -60.00   54
  6  \w     53.00  83.00   0.50    5.00    --  111.00 -61.00   0.00   60
  7  \w     38.00  73.00   0.50    5.00    --  111.00 -77.00   0.00   70
  8  \w     39.00 122.00   0.50    5.00    --  111.00 -77.00  60.00  166
  9  \w     48.00 103.00   0.50    5.00    --  111.00-125.00  30.00  110
 10  \w     31.00  90.00   0.50    5.00    --  111.00 -94.00 -90.00  118
 11  \w     47.00  99.00   0.50    5.00    --  111.00 -94.00-180.00  104
 12  \w     87.00 167.00   0.50    5.00    --  111.00  77.00  90.00  160
 13  \w    151.00 178.00   0.50    5.00    --  111.00  78.00 158.00   54
 14  \w    106.00 133.00   0.50    5.00    --  111.00  78.00 158.00   54
 15  \w     85.00 172.00   0.50    5.00    --  111.00  61.00 150.00  174
 16  \w    -20.00  34.00   0.50    1.25    --  -38.50  38.00 150.00  108
 17  \w    -96.00 -14.00   0.50    1.25    --  -38.50 -57.00  60.00  164
 18  \w   -109.00 -32.00   0.50    1.25    --  -38.50 -38.00 -30.00  154
;
_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      -0.0838432000
_diffrn_orient_matrix_UB_12      0.0097602000
_diffrn_orient_matrix_UB_13      0.0160610000
_diffrn_orient_matrix_UB_21      0.0119660000
_diffrn_orient_matrix_UB_22      -0.1028333000
_diffrn_orient_matrix_UB_23      0.0435155000
_diffrn_orient_matrix_UB_31      0.0309565000
_diffrn_orient_matrix_UB_32      0.0663990000
_diffrn_orient_matrix_UB_33      0.0651634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.688
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.769
_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    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         8707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0656P)^2^+1.6943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8017
_reflns_number_total             8707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_015.cif
_cod_data_source_block           jjw0602
_cod_original_cell_volume        4185.70(5)
_cod_database_code               4038376
_chemical_oxdiff_formula         'C148 H224 F12 N24 O16 P4 S4 '
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C),
 C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              37538
_shelx_hkl_checksum              38793
_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 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.786