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_4127874
_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, Br'
_chemical_formula_sum            'C56 H74 Br N6'
_chemical_formula_weight         911.12
_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                 109.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6261(4)
_cell_length_b                   16.5623(3)
_cell_length_c                   15.8057(3)
_cell_measurement_reflns_used    5585
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.1120
_cell_measurement_theta_min      4.0030
_cell_volume                     5325.49(18)
_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 (Shedlrick, 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 0.996
_diffrn_measured_fraction_theta_max 0.968
_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    -68.00  30.00   1.00    8.29    --  -43.01  57.00-120.00   98
  2  \w   -110.00 -83.00   1.00    8.29    --  -43.01 -99.00-150.00   27
  3  \w    -94.00 -22.00   1.00    8.29    --  -43.01 -37.00  60.00   72
  4  \w   -124.00 -99.00   1.00    8.29    --  -43.01 -99.00 -30.00   25
  5  \w     96.00 170.00   1.00   33.19    --  105.68 125.00 150.00   74
  6  \w     33.00 137.00   1.00   33.19    --  105.68 -77.00 120.00  104
  7  \w    148.00 173.00   1.00   33.19    --  105.68 125.00   0.00   25
  8  \w    111.00 138.00   1.00   33.19    --  105.68 -77.00 -60.00   27
  9  \w     31.00  80.00   1.00   33.19    --  105.68 -77.00 -60.00   49
 10  \w     77.00 176.00   1.00   33.19    --  105.68  61.00 -90.00   99
 11  \w     96.00 171.00   1.00   33.19    --  105.68  45.00-150.00   75
;
_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  0.0154
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11249
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.572
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.442
_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 dark green'
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       plate
_exptl_crystal_F_000             1948
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0466P)^2^+3.5915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4685
_reflns_number_total             5211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_005.cif
_cod_data_source_block           le-8-37
_cod_original_cell_volume        5325.50(19)
_cod_database_code               4127874
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.784
_shelx_res_checksum              38258
_shelx_hkl_checksum              10366