Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds.
Chaudhari, Moreshwar B.; Sutar, Yogesh; Malpathak, Shreyas; Hazra, Anirban; Gnanaprakasam, Boopathy; Organic letters 19 (2017) 3628–3631; doi:10.1021/acs.orglett.7b01616

data_1547097
_publ_section_title
;
 Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3628
_journal_page_last               3631
_journal_paper_doi               10.1021/acs.orglett.7b01616
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.136(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.241(4)
_cell_length_b                   5.7694(18)
_cell_length_c                   18.543(6)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.39
_cell_volume                     1284.9(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20968
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.409
_diffrn_reflns_theta_min         1.842
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.1097
_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^)+(0.1590P)^2^+8.8223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3820
_refine_ls_wR_factor_ref         0.3919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2499
_reflns_number_total             3211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01616_si_002.cif
_cod_data_source_block           Compound2a
_cod_database_code               1547097
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              43652
_shelx_hkl_checksum              42542