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_4038375
_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         'C10 H8 N2 P, C F3 O3 S'
_chemical_formula_sum            'C11 H8 F3 N2 O3 P S'
_chemical_formula_weight         336.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                95.055(3)
_cell_angle_beta                 99.126(3)
_cell_angle_gamma                109.450(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2241(5)
_cell_length_b                   9.0577(7)
_cell_length_c                   10.9162(8)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.107
_cell_measurement_theta_min      2.841
_cell_volume                     657.34(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.123
_diffrn_reflns_theta_min         1.911
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0332 before and 0.0287 after correction.
The Ratio of minimum to maximum transmission is 0.9315.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0468P)^2^+0.2272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3277
_reflns_number_total             3836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00577_si_001.cif
_cod_data_source_block           jjw0327
_cod_original_cell_volume        657.34(8)
_cod_database_code               4038375
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C5(H5), C11(H11), C3(H3), C10(H10), C4(H4)
;
_shelx_res_checksum              73546
_shelx_hkl_checksum              27267
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-11
_olex2_date_sample_submission    2015-03-11
_olex2_submission_original_sample_id jjw0327
_olex2_submission_special_instructions 'No special instructions were received'