Catalyst-Controlled Aliphatic C-H Oxidations with a Predictive Model for Site-Selectivity
Paul E. Gormisky; M. Christina White; Journal of the American Chemical Society 135 (2013) 14052–14055; doi:10.1021/ja407388y

data_4120848
_publ_section_title
;
 Catalyst-Controlled Aliphatic C-H Oxidations with a Predictive Model for
 Site-Selectivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14052
_journal_page_last               14055
_journal_paper_doi               10.1021/ja407388y
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C33 H37 Br O10), 3(C3 H6 O)'
_chemical_formula_sum            'C75 H92 Br2 O23'
_chemical_formula_weight         1521.31
_space_group_IT_number           1
_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
_audit_update_record
; 
? 
;
_cell_angle_alpha                92.273(4)
_cell_angle_beta                 104.028(4)
_cell_angle_gamma                101.858(4)
_cell_formula_units_Z            1
_cell_length_a                   9.516(3)
_cell_length_b                   14.050(4)
_cell_length_c                   14.830(4)
_cell_measurement_reflns_used    2693
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      19.14
_cell_measurement_theta_min      2.15
_cell_volume                     1874.2(9)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2010.11-3 (Bruker, 2010)'
_computing_data_reduction
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  bm64uas
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15375
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    1.156
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_correction_T_min  0.7795
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       needle
_exptl_crystal_F_000             796
_exptl_crystal_id                bm64uas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-3 -1 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack (1983),  4805 Friedels'
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1013
_refine_ls_number_reflns         11581
_refine_ls_number_restraints     252
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                8461
_reflns_number_total             11581
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja407388y_si_004.cif
_cod_data_source_block           bm64uas
_cod_original_cell_volume        1874.1(9)
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4120848
_refine_ls_abs_structure_hooft   0.028(6)