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_4127876
_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 H73 N6 O, Cl, 3.1(C H2 Cl2)'
_chemical_formula_sum            'C59.1 H79.2 Cl7.2 N6 O'
_chemical_formula_weight         1144.92
_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                75.750(4)
_cell_angle_beta                 79.343(4)
_cell_angle_gamma                89.726(4)
_cell_formula_units_Z            2
_cell_length_a                   12.2645(7)
_cell_length_b                   16.6638(8)
_cell_length_c                   17.0136(6)
_cell_measurement_reflns_used    6598
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.0200
_cell_measurement_theta_min      2.7250
_cell_volume                     3309.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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 0.998
_diffrn_measured_fraction_theta_max 0.958
_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    -99.00 -16.00   1.00    5.00    --  -40.41 -38.00 -60.00   83
  2  \w   -103.00 -21.00   1.00    5.00    --  -40.41 -38.00  30.00   82
  3  \w    -45.00  31.00   1.00    5.00    --  -40.41  38.00-180.00   76
  4  \w   -114.00 -57.00   1.00    5.00    --  -40.41-158.00 159.00   57
  5  \w     53.00  95.00   1.00    5.00    --   40.41-125.00  30.00   42
  6  \w     31.00  78.00   1.00    5.00    --   40.41 -99.00  90.00   47
  7  \w      9.00  81.00   1.00    5.00    --   40.41  77.00-150.00   72
  8  \w     31.00 162.00   1.00   20.00    --  112.00 -15.00  60.00  131
  9  \w     37.00 138.00   1.00   20.00    --  112.00 -30.00-120.00  101
 10  \w    108.00 133.00   1.00   20.00    --  112.00 125.00 -30.00   25
 11  \w     47.00 139.00   1.00   20.00    --  112.00 -61.00 120.00   92
 12  \w     59.00 118.00   1.00   20.00    --  112.00-125.00  90.00   59
 13  \w     91.00 118.00   1.00   20.00    --  112.00-125.00-150.00   27
 14  \w     99.00 171.00   1.00   20.00    --  112.00 125.00-150.00   72
 15  \w     47.00 103.00   1.00   20.00    --  112.00-125.00-180.00   56
 16  \w     40.00 118.00   1.00   20.00    --  112.00-125.00 -60.00   78
 17  \w     86.00 177.00   1.00   20.00    --  112.00  45.00  60.00   91
 18  \w     51.00  83.00   1.00   20.00    --  112.00 -30.00  30.00   32
 19  \w     48.00 142.00   1.00   20.00    --  112.00 -77.00 -90.00   94
;
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23774
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.557
_diffrn_reflns_theta_min         2.729
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  0.530
_exptl_absorpt_correction_T_min  0.180
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       plate
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.689
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.233
_refine_diff_density_max         1.648
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     738
_refine_ls_number_reflns         13339
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0797
_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^)+(0.1550P)^2^+1.5810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2330
_refine_ls_wR_factor_ref         0.2596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9752
_reflns_number_total             13339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_009.cif
_cod_data_source_block           le-7-94
_cod_original_formula_sum        'C59.10 H79.20 Cl7.20 N6 O'
_cod_database_code               4127876
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.222
_shelx_estimated_absorpt_t_max   0.530
_shelx_res_checksum              38637
_shelx_hkl_checksum              54332