Chemo- and regioselective oxygenation of C(sp3)–H bonds in aliphatic alcohols using a covalently bound directing activator and atmospheric oxygen
Ozawa, Jun; Tashiro, Masayuki; Ni, Jizhi; Oisaki, Kounosuke; Kanai, Motomu; Chem. Sci. 7 (2016) 1904–; doi:10.1039/C5SC04476F

data_1540579
_publ_section_title
;
 Chemo- and regioselective oxygenation of C(sp3)--H bonds in aliphatic
 alcohols using a covalently bound directing activator and atmospheric
 oxygen
;
_journal_issue                   3
_journal_name_full               'Chem. Sci.'
_journal_page_first              1904
_journal_paper_doi               10.1039/C5SC04476F
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_sum            'C26 H29 F3 N2 O5'
_chemical_formula_weight         506.51
_chemical_name_systematic        O-(4-nitrobenzyl)-(R)-1k
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-29 deposited with the CCDC.
2015-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9683(2)
_cell_length_b                   12.0495(3)
_cell_length_c                   25.4584(5)
_cell_measurement_reflns_used    14625
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.5
_cell_volume                     2444.36(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27367
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_coef       0.0065(11)
_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   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0905
_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^)+(0.1619P)^2^+2.3782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.3199
_reflns_number_gt                2507
_reflns_number_total             4475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc04476f2.cif
_cod_data_source_block           ozw02
_cod_depositor_comments          'Adding full bibliography for 1540579.cif.'
_cod_database_code               1540579