Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes.
Savva, Anastasia C.; Mirallai, Styliana I.; Zissimou, Georgia A.; Berezin, Andrey A.; Demetriades, Marina; Kourtellaris, Andreas; Constantinides, Christos P.; Nicolaides, Constantinos; Trypiniotis, Theodossis; Koutentis, Panayiotis A.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b01297

data_4032601
_publ_section_title
;
 Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of
 N Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b01297
_journal_year                    2017
_chemical_formula_moiety         'C13 H5 F5 N2 O'
_chemical_formula_sum            'C13 H5 F5 N2 O'
_chemical_formula_weight         300.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                80.949(5)
_cell_angle_beta                 79.134(5)
_cell_angle_gamma                78.079(5)
_cell_formula_units_Z            2
_cell_length_a                   7.369(5)
_cell_length_b                   7.894(5)
_cell_length_c                   10.285(5)
_cell_measurement_reflns_used    1226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7680
_cell_measurement_theta_min      3.7570
_cell_volume                     570.5(6)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3563
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.140
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_description       polyhedra
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0492P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1464
_reflns_number_total             2008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01297_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4032601
_shelx_shelxl_version_number     2016/4
_shelx_res_checksum              35406
_shelx_hkl_checksum              49748