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_4127873
_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         'C40 H42 N6'
_chemical_formula_sum            'C40 H42 N6'
_chemical_formula_weight         606.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.984(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.56119(15)
_cell_length_b                   11.3903(2)
_cell_length_c                   20.3054(5)
_cell_measurement_reflns_used    5051
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.9980
_cell_measurement_theta_min      4.3250
_cell_volume                     1747.74(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Mercury 4.1.2 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.988
_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    -67.00  22.00   1.00    8.89    --  -43.01  37.00 -60.00   89
  2  \w   -117.00 -21.00   1.00    8.89    --  -43.01 -37.00 120.00   96
  3  \w   -110.00 -82.00   1.00    8.89    --  -43.01 -99.00 -90.00   28
  4  \w   -123.00 -96.00   1.00    8.89    --  -43.01 -99.00-150.00   27
  5  \w     55.00  82.00   1.00    8.89    --   43.01-125.00-180.00   27
  6  \w     10.00  83.00   1.00    8.89    --   43.01 -99.00  30.00   73
  7  \w     39.00 134.00   1.00   35.57    --  105.68 -30.00  30.00   95
  8  \w     48.00  75.00   1.00   35.57    --  105.68-125.00  30.00   27
  9  \w     81.00 177.00   1.00   35.57    --  105.68  45.00-150.00   96
 10  \w     37.00 131.00   1.00   35.57    --  105.68 -77.00  60.00   94
 11  \w     29.00 144.00   1.00   35.57    --  105.68 -15.00-150.00  115
 12  \w     78.00 118.00   1.00   35.57    --  105.68-125.00  30.00   40
 13  \w    107.00 174.00   1.00   35.57    --  105.68 125.00 150.00   67
 14  \w    122.00 176.00   1.00   35.57    --  105.68 125.00 -30.00   54
 15  \w    103.00 132.00   1.00   35.57    --  105.68 -61.00 120.00   29
 16  \w     74.00 101.00   1.00   35.57    --  105.68 -94.00-120.00   27
 17  \w     93.00 118.00   1.00   35.57    --  105.68-125.00-180.00   25
 18  \w     34.00 111.00   1.00   35.57    --  105.68 -45.00-150.00   77
;
_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_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11884
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.523
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.153
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0017(3)
_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   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0525P)^2^+0.3281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3005
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_003.cif
_cod_data_source_block           pv052
_cod_original_cell_volume        1747.73(7)
_cod_database_code               4127873
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.821
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              94090
_shelx_hkl_checksum              88557