C-C Cross-Coupling Reactions of Trityl Radicals: Spin Density Delocalization, Exchange Coupling, and a Spin Label.
Fleck, Nico; Hett, Tobias; Brode, Jonas; Meyer, Andreas; Richert, Sabine; Schiemann, Olav; The Journal of organic chemistry 84 (2019) 3293–3303; doi:10.1021/acs.joc.8b03229

data_4033930
_publ_section_title
;
 C-C Cross-Coupling Reactions of Trityl Radicals: Spin Density
 Delocalization, Exchange Coupling, and a Spin Label.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3293
_journal_page_last               3303
_journal_paper_doi               10.1021/acs.joc.8b03229
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H37 I3 O S12, C4 H10 O'
_chemical_formula_sum            'C41 H47 I3 O2 S12'
_chemical_formula_weight         1337.20
_chemical_name_systematic        NFL-T22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.4750(8)
_cell_length_b                   10.6566(3)
_cell_length_c                   18.4500(6)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.21
_cell_volume                     5205.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing \w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1364
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            87159
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.337
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3729
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1794 before and 0.1103 after correction. The Ratio of minimum to maximum transmission is 0.4999. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       plate
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.887
_refine_diff_density_min         -1.319
_refine_diff_density_rms         0.172
_refine_ls_abs_structure_details
;
 Flack x determined using 4077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.068(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         12545
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0480P)^2^+25.5478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                10736
_reflns_number_total             12545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03229_si_002.cif
_cod_data_source_block           5471f
_cod_database_code               4033930
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C40(H40A,H40B)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C),
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C41(H41A,H41B,H41C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              60893
_shelx_hkl_checksum              30065
_olex2_submission_special_instructions 'No special instructions were received'