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_1550993
_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         'C56 H76 Li2 N10 O6'
_chemical_formula_sum            'C56 H76 Li2 N10 O6'
_chemical_formula_weight         999.14
_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   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                 91.9104(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2403(2)
_cell_length_b                   16.0729(2)
_cell_length_c                   17.9830(3)
_cell_measurement_reflns_used    8082
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.5760
_cell_measurement_theta_min      4.6930
_cell_volume                     3247.08(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.980
_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  30.00   1.00    2.50    --  -43.01  37.00 -90.00   97
  2  \w     23.00  94.00   1.00    2.50    --   43.01-125.00 -30.00   71
  3  \w     36.00 125.00   1.00   10.00    --  109.26 -45.00  30.00   89
  4  \w    124.00 164.00   1.00   10.00    --  109.26  30.00  60.00   40
  5  \w     82.00 128.00   1.00   10.00    --  109.26 -77.00-150.00   46
  6  \w     71.00 116.00   1.00   10.00    --  109.26-111.00-120.00   45
  7  \w     53.00 117.00   1.00   10.00    --  109.26 -45.00 -90.00   64
  8  \w     62.00 103.00   1.00   10.00    --  109.26-111.00  30.00   41
  9  \w     69.00 133.00   1.00   10.00    --  109.26 -77.00  90.00   64
 10  \w     56.00 116.00   1.00   10.00    --  109.26-111.00  90.00   60
 11  \w     25.00  99.00   1.00    2.50    --   43.01-125.00  60.00   74
 12  \w     34.00  60.00   1.00   10.00    --  109.26-111.00-120.00   26
 13  \w     42.00 133.00   1.00   10.00    --  109.26 -45.00-180.00   91
 14  \w    152.00 178.00   1.00   10.00    --  109.26  61.00-180.00   26
 15  \w     84.00 110.00   1.00   10.00    --  109.26  61.00-180.00   26
 16  \w     30.00 174.00   1.00   10.00    --  109.26   0.00-150.00  144
 17  \w   -113.00 -19.00   1.00    2.50    --  -43.01 -37.00  90.00   94
 18  \w   -121.00 -96.00   1.00    2.50    --  -43.01 -99.00-180.00   25
 19  \w   -122.00 -89.00   1.00    2.50    --  -43.01 -99.00-120.00   33
 20  \w   -124.00 -99.00   1.00    2.50    --  -43.01 -99.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, 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  0.0257
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.453
_diffrn_reflns_theta_min         3.689
_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  1.000
_exptl_absorpt_correction_T_min  0.203
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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 yellow'
_exptl_crystal_density_diffrn    1.022
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6605
_refine_ls_number_restraints     348
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0593
_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^)+(0.1161P)^2^+0.6157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.1949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5230
_reflns_number_total             6605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01502g2.cif
_cod_data_source_block           yzl719
_cod_original_cell_volume        3247.07(10)
_cod_database_code               1550993
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.761
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              65083
_shelx_fab_checksum              25106