Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.
Howell, Jennifer M.; Feng, Kaibo; Clark, Joseph R.; Trzepkowski, Louis J.; White, M. Christina; Journal of the American Chemical Society 137 (2015) 14590–14593; doi:10.1021/jacs.5b10299

data_4129751
_publ_contact_author
; 
M. Christina White 
University of Illinois 
School of Chemical Sciences 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14590
_journal_page_last               14593
_journal_paper_doi               10.1021/jacs.5b10299
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H35 N O3'
_chemical_formula_sum            'C26 H35 N O3'
_chemical_formula_weight         409.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 98.217(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4928(18)
_cell_length_b                   7.5529(13)
_cell_length_c                   13.883(2)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.02
_cell_measurement_theta_min      4.26
_cell_volume                     1088.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4, TWINABS V2012/1 
(Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-4 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  cd66ssa
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14626
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.014
_diffrn_reflns_theta_min         3.216
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.96348
_exptl_absorpt_correction_T_min  0.87764
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             444
_exptl_crystal_id                cd66ssa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 -2 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack (1983),  1896 Friedels'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.066(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0487P)^2^+0.1988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4163
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10299_si_003.cif
_cod_data_source_block           cd66ssa
_cod_original_cell_volume        1089.0(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129751
_shelx_estimated_absorpt_t_min   0.802
_shelx_estimated_absorpt_t_max   0.952
_shelxl_version_number           2014/6
_shelx_res_checksum              63483
_shelx_hkl_checksum              70241