Synthesis of aminyl biradicals by base-induced Csp3–Csp3 coupling of cationic azo dyes
Liu, Yizhu; Varava, Paul; Fabrizio, Alberto; Eymann, Léonard Y. M.; Tskhovrebov, Alexander G.; Planes, Ophélie Marie; Solari, Euro; Fadaei-Tirani, Farzaneh; Scopelliti, Rosario; Sienkiewicz, Andrzej; Corminboeuf, Clémence; Severin, Kay; Chemical Science  (2019) –; doi:10.1039/C9SC01502G

data_1550994
_publ_section_title
;
 Synthesis of aminyl biradicals by base-induced Csp3--Csp3 coupling of
 cationic azo dyes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01502G
_journal_year                    2019
_chemical_formula_moiety         'C98 H144 K2 N10 O10'
_chemical_formula_sum            'C98 H144 K2 N10 O10'
_chemical_formula_weight         1700.42
_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
_audit_update_record
;
2019-03-18 deposited with the CCDC.    2019-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                83.132(7)
_cell_angle_beta                 89.742(7)
_cell_angle_gamma                66.134(9)
_cell_formula_units_Z            1
_cell_length_a                   12.4584(12)
_cell_length_b                   13.8311(12)
_cell_length_c                   16.8496(14)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      68.0830
_cell_measurement_theta_min      3.5210
_cell_volume                     2633.0(4)
_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      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_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    -15.00  34.00   1.00   10.00    --  -40.91  77.00-120.00   49
  2  \w   -104.00 -16.00   1.00   10.00    --  -40.91 -38.00 150.00   88
  3  \w    -65.00  33.00   1.00   10.00    --  -40.91  38.00 -30.00   98
  4  \w    -91.00  -3.00   1.00   10.00    --  -40.91 125.00 -30.00   88
  5  \w    -44.00  -4.00   1.00   10.00    --  -40.91 125.00  60.00   40
  6  \w     13.00  55.00   1.00   10.00    --   40.91  77.00 120.00   42
  7  \w     87.00 122.00   1.00   10.00    --   40.91-171.00 -79.00   35
  8  \w     64.00 131.00   1.00   40.00    --  111.85 -30.00  90.00   67
  9  \w     44.00 132.00   1.00   40.00    --  111.85 -61.00   0.00   88
 10  \w     36.00 140.00   1.00   40.00    --  111.85 -30.00 -90.00  104
 11  \w     87.00 175.00   1.00   40.00    --  111.85  45.00  90.00   88
 12  \w     89.00 130.00   1.00   40.00    --  111.85  30.00 -90.00   41
 13  \w     87.00 165.00   1.00   40.00    --  111.85  45.00 150.00   78
 14  \w     45.00 118.00   1.00   40.00    --  111.85-125.00 -90.00   73
 15  \w     41.00 105.00   1.00   40.00    --  111.85-125.00 -30.00   64
 16  \w     86.00 118.00   1.00   40.00    --  111.85-125.00  90.00   32
 17  \w     82.00 109.00   1.00   40.00    --  111.85-125.00-180.00   27
 18  \w     45.00 106.00   1.00   40.00    --  111.85 -94.00 -30.00   61
 19  \w     34.00  64.00   1.00   40.00    --  111.85 -94.00 -90.00   30
 20  \w     79.00 141.00   1.00   40.00    --  111.85 -77.00  60.00   62
;
_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  0.0633
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18769
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.009
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.233
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.512
_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 red'
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         10601
_refine_ls_number_restraints     1361
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0951
_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^)+(0.1551P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2621
_refine_ls_wR_factor_ref         0.3248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5116
_reflns_number_total             10601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01502g2.cif
_cod_data_source_block           yzl797
_cod_database_code               1550994
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.524
_shelx_estimated_absorpt_t_max   0.804
_shelx_res_checksum              26973
_shelx_fab_checksum              56562