Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins.
Eymann, Léonard Y M; Varava, Paul; Shved, Andrei M.; Curchod, Basile F. E.; Liu, Yizhu; Planes, Ophélie M; Sienkiewicz, Andrzej; Scopelliti, Rosario; Fadaei Tirani, Farzaneh; Severin, Kay; Journal of the American Chemical Society 141 (2019) 17112–17116; doi:10.1021/jacs.9b10660

data_4127871
_publ_section_title
;
 Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide
 with N-Heterocyclic Olefins.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17112
_journal_page_last               17116
_journal_paper_doi               10.1021/jacs.9b10660
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C56 H74 N6, C2 F6 N O4 S2'
_chemical_formula_sum            'C58 H74 F6 N7 O4 S2'
_chemical_formula_weight         1111.36
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                70.545(3)
_cell_angle_beta                 88.449(3)
_cell_angle_gamma                61.047(4)
_cell_formula_units_Z            1
_cell_length_a                   11.9866(4)
_cell_length_b                   12.3158(5)
_cell_length_c                   12.5454(5)
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.4820
_cell_measurement_theta_min      3.7670
_cell_volume                     1507.67(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury 4.0.0 (CCDC, 2018)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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   -113.00 -17.00   1.00    2.00    --  -40.91 -38.00 -30.00   96
  2  \w    -22.00  22.00   1.00    2.00    --  -40.91  77.00 120.00   44
  3  \w    -72.00 -23.00   1.00    2.00    --  -40.91  77.00 120.00   49
  4  \w   -107.00 -16.00   1.00    2.00    --  -40.91 -57.00-120.00   91
  5  \w     45.00  90.00   1.00    2.00    --   40.91-125.00 -30.00   45
  6  \w     20.00  51.00   1.00    2.00    --   40.91 -99.00-180.00   31
  7  \w     88.00 164.00   1.00    8.00    --  107.03  77.00 -90.00   76
  8  \w     35.00  62.00   1.00    8.00    --  107.03-125.00 -90.00   27
  9  \w     38.00 107.00   1.00    8.00    --  107.03 -61.00 -30.00   69
 10  \w     35.00 128.00   1.00    8.00    --  107.03 -61.00-150.00   93
 11  \w     26.00 110.00   1.00    8.00    --  107.03 -94.00  60.00   84
 12  \w     79.00 118.00   1.00    8.00    --  107.03-125.00 -90.00   39
 13  \w     81.00 108.00   1.00    8.00    --  107.03  45.00   0.00   27
 14  \w     31.00  75.00   1.00    8.00    --  107.03 -30.00  30.00   44
 15  \w     82.00 118.00   1.00    8.00    --  107.03-125.00   0.00   36
 16  \w    104.00 133.00   1.00    8.00    --  107.03 -30.00  30.00   29
 17  \w     25.00  70.00   1.00    8.00    --  107.03 -94.00-150.00   45
 18  \w     36.00 113.00   1.00    8.00    --  107.03 -77.00 120.00   77
 19  \w     21.00 154.00   1.00    8.00    --  107.03   0.00 -90.00  133
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.660
_diffrn_reflns_theta_min         3.787
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
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 intense blue'
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       prism
_exptl_crystal_F_000             589
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.4169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5377
_reflns_number_total             5879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_006.cif
_cod_data_source_block           le-8-31
_cod_original_cell_volume        1507.68(11)
_cod_database_code               4127871
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.661
_shelx_estimated_absorpt_t_max   0.807
_shelx_res_checksum              83675
_shelx_hkl_checksum              9408