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_1550992
_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         'C58 H64 N10, 2(C4 H8 O)'
_chemical_formula_sum            'C66 H80 N10 O2'
_chemical_formula_weight         1045.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 91.3424(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2045(3)
_cell_length_b                   19.1034(3)
_cell_length_c                   20.0726(3)
_cell_measurement_reflns_used    11802
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.5190
_cell_measurement_theta_min      7.7270
_cell_volume                     5828.64(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      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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    -69.00  28.00   1.00    1.91    --  -40.91  57.00-150.00   97
  2  \w   -112.00 -17.00   1.00    1.91    --  -40.91 -57.00  60.00   95
  3  \w     90.00 117.00   1.00    1.91    --   40.91  77.00  60.00   27
  4  \w    -30.00  -1.00   1.00    1.91    --   40.91 -57.00 -60.00   29
  5  \w      7.00  81.00   1.00    1.91    --   40.91 -99.00 -60.00   74
  6  \w    -15.00  43.00   1.00    1.91    --   40.91 -38.00 -60.00   58
  7  \w      9.00  34.00   1.00    1.91    --   40.91  77.00  60.00   25
  8  \w     35.00 136.00   1.00    7.65    --  107.03 -61.00  90.00  101
  9  \w     75.00 118.00   1.00    7.65    --  107.03-125.00 -90.00   43
 10  \w     88.00 178.00   1.00    7.65    --  107.03  45.00-180.00   90
 11  \w     93.00 121.00   1.00    7.65    --  107.03 -45.00 -60.00   28
 12  \w     35.00  64.00   1.00    7.65    --  107.03 -45.00 -60.00   29
 13  \w     37.00 117.00   1.00    7.65    --  107.03-125.00  60.00   80
 14  \w     90.00 178.00   1.00    7.65    --  107.03  45.00-120.00   88
 15  \w     33.00 113.00   1.00    7.65    --  107.03 -77.00-120.00   80
 16  \w    108.00 150.00   1.00    7.65    --  107.03  30.00 120.00   42
 17  \w     84.00 115.00   1.00    7.65    --  107.03-125.00-180.00   31
 18  \w     34.00  60.00   1.00    7.65    --  107.03-125.00-180.00   26
 19  \w     82.00 145.00   1.00    7.65    --  107.03  45.00 -30.00   63
 20  \w     37.00  99.00   1.00    7.65    --  107.03-125.00 120.00   62
 21  \w     63.00 108.00   1.00    7.65    --  107.03 -30.00-180.00   45
;
_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_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14115
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.757
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.249
_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 red'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       prism
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.363
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     735
_refine_ls_number_reflns         14115
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0893P)^2^+0.3906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11958
_reflns_number_total             14115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01502g2.cif
_cod_data_source_block           yzl797b
_cod_database_code               1550992
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.819
_shelx_res_checksum              22961