Toluene and Ethylbenzene Aliphatic C-H Bond Oxidations Initiated by a Dicopper(II)-μ-1,2-Peroxo Complex
Heather R. Lucas; Lei Li; Amy A. Narducci Sarjeant; Michael A. Vance; Edward I. Solomon; Kenneth D. Karlin; Journal of the American Chemical Society 131 (2009) 3230–3245; doi:10.1021/ja807081d

data_4104264
_publ_section_title
;
 Toluene and Ethylbenzene Aliphatic C-H Bond Oxidations Initiated by a
 Dicopper(II)-\m-1,2-Peroxo Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3230
_journal_page_last               3245
_journal_paper_doi               10.1021/ja807081d
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C21 H22 Cu N4, C24 B F20, 0.5(C7 H16)'
_chemical_formula_sum            'C48.5 H30 B Cu F20 N4'
_chemical_formula_weight         1123.11
_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_date
;
'Mon Jul 17 11:33:31 2006'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.14(3)
_cell_angle_beta                 104.071(19)
_cell_angle_gamma                97.69(2)
_cell_formula_units_Z            2
_cell_length_a                   13.023(3)
_cell_length_b                   13.409(4)
_cell_length_c                   15.048(3)
_cell_measurement_reflns_used    4408
_cell_measurement_theta_max      27.4990
_cell_measurement_theta_min      3.7389
_cell_volume                     2285.4(12)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' omega scans'
_diffrn_orient_matrix_UB_11      0.0382300959
_diffrn_orient_matrix_UB_12      0.0307035291
_diffrn_orient_matrix_UB_13      0.0489732151
_diffrn_orient_matrix_UB_21      -0.0039279026
_diffrn_orient_matrix_UB_22      0.0499807793
_diffrn_orient_matrix_UB_23      -0.0046738680
_diffrn_orient_matrix_UB_31      -0.0431402087
_diffrn_orient_matrix_UB_32      0.0029812645
_diffrn_orient_matrix_UB_33      0.0209967752
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_sigmaI/netI    0.1599
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19421
_diffrn_reflns_resolution_max    0.85
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         3.75
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1126
_exptl_crystal_size_max          0.2747
_exptl_crystal_size_mid          0.1161
_exptl_crystal_size_min          0.0097
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                4168
_reflns_number_total             7713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807081d_si_007.cif
_cod_data_source_block           x0269
_cod_original_cell_volume        2285.5(12)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        'C48.50 H30 B Cu F20 N4'
_cod_database_code               4104264
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_cell_measurement_resolution_max 0.77
_jhu_your_name_here              'Dr. Amy A Sarjeant'
_jhu_your_lab_here               'NCB 240'
_jhu_your_phone_number_here      x6-8569
_jhu_your_email_here             xray@jhu.edu
_jhu_institutional_source        'Karlin Lab'
_jhu_submitting_scientist        'Heather Lucas'
_jhu_scientist_phone             x6-6161
_jhu_scientist_email             hlucas4@jhu.edu
_jhu_identifying_number          x0269
_jhu_xray_labbook                II-17
_jhu_crystalization_labbook
;
;
_jhu_crystalization_solvent      'Ether, Pentane'
_jhu_crystalization_method
;
;
_jhu_diffraction_detector_distance 50
_jhu_quality_factor              3