C–H Bond Amination by Photochemically Generated Transient Borylnitrenes at Room Temperature: A Combined Experimental and Theoretical Investigation of the Insertion Mechanism and Influence of Substituents
Filthaus, Matthias; Schwertmann, Larissa; Neuhaus, Patrik; Seidel, Rüdiger W.; Oppel, Iris M.; Bettinger, Holger F.; Organometallics 31 (2012) 3894–; doi:10.1021/om300063y

data_4078231
_publ_section_title
;
 C--H Bond Amination by Photochemically Generated Transient Borylnitrenes
 at Room Temperature: A Combined Experimental and Theoretical
 Investigation of the Insertion Mechanism and Influence of Substituents
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3894
_journal_paper_doi               10.1021/om300063y
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C6 H2 Cl4 O2, 3(H2 O)'
_chemical_formula_sum            'C6 H8 Cl4 O5'
_chemical_formula_weight         301.92
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.021(15)
_cell_angle_beta                 110.272(16)
_cell_angle_gamma                91.240(13)
_cell_formula_units_Z            2
_cell_length_a                   6.6762(11)
_cell_length_b                   9.5002(15)
_cell_length_c                   9.5558(17)
_cell_measurement_reflns_used    1286
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      28.2329
_cell_measurement_theta_min      3.2668
_cell_volume                     534.98(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur^TM^2, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2893
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.1583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2446
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300063y_si_001.cif
_cod_data_source_block           tetrachlorocatechol
_cod_original_cell_volume        534.97(18)
_cod_database_code               4078231