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_4127869
_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, Cl'
_chemical_formula_sum            'C56 H74 Cl N6'
_chemical_formula_weight         866.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                90
_cell_angle_beta                 109.082(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4308(5)
_cell_length_b                   16.6188(4)
_cell_length_c                   15.7436(4)
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.1520
_cell_measurement_theta_min      7.4650
_cell_volume                     5299.0(2)
_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 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -117.00 -80.00   1.00    7.50    --  -43.26 -99.00 -30.00   37
  2  \w   -108.00 -17.00   1.00    7.50    --  -43.26 -57.00-150.00   91
  3  \w   -119.00 -92.00   1.00    7.50    --  -43.26 -99.00 -90.00   27
  4  \w    -87.00 -20.00   1.00    7.50    --  -43.26 125.00  60.00   67
  5  \w    -68.00  29.00   1.00    7.50    --  -43.26  57.00   0.00   97
  6  \w     70.00 109.00   1.00   30.00    --  105.68 -94.00 -60.00   39
  7  \w     57.00 123.00   1.00   30.00    --  105.68 -30.00  30.00   66
  8  \w     77.00 128.00   1.00   30.00    --  105.68 -45.00-150.00   51
  9  \w     47.00 132.00   1.00   30.00    --  105.68 -77.00 120.00   85
 10  \w    135.00 160.00   1.00   30.00    --  105.68 125.00  90.00   25
 11  \w     32.00 103.00   1.00   30.00    --  105.68 -94.00  30.00   71
 12  \w     79.00 172.00   1.00   30.00    --  105.68  30.00  30.00   93
 13  \w     35.00 114.00   1.00   30.00    --  105.68 -30.00 120.00   79
 14  \w     23.00  53.00   1.00   30.00    --  105.68 -94.00  60.00   30
 15  \w    103.00 171.00   1.00   30.00    --  105.68 125.00  30.00   68
 16  \w     80.00 165.00   1.00   30.00    --  105.68  45.00  90.00   85
 17  \w     84.00 109.00   1.00   30.00    --  105.68 -94.00  60.00   25
 18  \w    102.00 128.00   1.00   30.00    --  105.68 125.00  90.00   26
 19  \w     93.00 118.00   1.00   30.00    --  105.68-125.00-120.00   25
 20  \w     70.00 105.00   1.00   30.00    --  105.68 -61.00   0.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_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_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.606
_diffrn_reflns_theta_min         3.440
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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 green'
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_description       prism
_exptl_crystal_F_000             1876
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6110
_refine_ls_number_restraints     374
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0582
_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^)+(0.1141P)^2^+1.2164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4620
_reflns_number_total             6110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_004.cif
_cod_data_source_block           le-8-21-2
_cod_database_code               4127869
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.845
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              16788
_shelx_hkl_checksum              11636