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_4127872
_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, 2(Br3)'
_chemical_formula_sum            'C56 H74 Br6 N6'
_chemical_formula_weight         1310.67
_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                69.420(5)
_cell_angle_beta                 63.201(5)
_cell_angle_gamma                84.213(4)
_cell_formula_units_Z            1
_cell_length_a                   12.0287(6)
_cell_length_b                   12.3634(6)
_cell_length_c                   12.9443(7)
_cell_measurement_reflns_used    5419
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8230
_cell_measurement_theta_min      3.8170
_cell_volume                     1604.77(17)
_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      100.00(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 0.970
_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   -110.00 -22.00   1.00    1.00    --  -43.01 -57.00 -30.00   88
  2  \w    -71.00  30.00   1.00    1.00    --  -43.01  57.00 120.00  101
  3  \w   -116.00 -89.00   1.00    1.00    --  -43.01 -99.00 120.00   27
  4  \w   -123.00 -81.00   1.00    1.00    --  -43.01 -99.00  60.00   42
  5  \w    -89.00 -64.00   1.00    1.00    --  -43.01 125.00-180.00   25
  6  \w      9.00  83.00   1.00    1.00    --   43.01 -99.00-120.00   74
  7  \w     47.00 112.00   1.00    3.00    --  109.26-111.00  60.00   65
  8  \w    128.00 174.00   1.00    3.00    --  109.26  30.00 -30.00   46
  9  \w     58.00 178.00   1.00    3.00    --  109.26  15.00 -90.00  120
 10  \w     37.00 135.00   1.00    3.00    --  109.26 -61.00 150.00   98
 11  \w     34.00 127.00   1.00    3.00    --  109.26 -30.00  30.00   93
 12  \w     43.00 138.00   1.00    3.00    --  109.26 -30.00 -90.00   95
 13  \w     73.00  98.00   1.00    3.00    --  109.26-111.00 -90.00   25
 14  \w     83.00 125.00   1.00    3.00    --  109.26  30.00 -30.00   42
 15  \w     88.00 113.00   1.00    3.00    --  109.26-111.00 -60.00   25
 16  \w     41.00  71.00   1.00    3.00    --  109.26-111.00 -60.00   30
 17  \w     78.00 136.00   1.00    3.00    --  109.26 -77.00-120.00   58
 18  \w     86.00 112.00   1.00    3.00    --  109.26-111.00-180.00   26
 19  \w     33.00 120.00   1.00    3.00    --  109.26 -77.00  60.00   87
;
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         3.828
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.793
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.483
_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 orange'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.00032(7)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.1497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5580
_reflns_number_total             6443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10660_si_008.cif
_cod_data_source_block           le-7-86
_cod_original_cell_volume        1604.77(16)
_cod_database_code               4127872
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.424
_shelx_estimated_absorpt_t_max   0.551
_shelx_res_checksum              61819
_shelx_hkl_checksum              13426
_shelx_fab_checksum              59409