Chemoselective methylene oxidation in aromatic molecules
Jinpeng Zhao; Takeshi Nanjo; Emilio C. de Lucca Jr; M. Christina White; Nature Chemistry 11 (2019) 213–221; doi:10.1038/s41557-018-0175-8

data_1551358
_publ_section_title
;
 Chemoselective methylene oxidation in aromatic molecules
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              213
_journal_page_last               221
_journal_paper_doi               10.1038/s41557-018-0175-8
_journal_volume                  11
_journal_year                    2019
_chemical_absolute_configuration 'ad, syn'
_chemical_formula_moiety         'C27 H32 O7'
_chemical_formula_sum            'C27 H32 O7'
_chemical_formula_weight         468.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 97.5430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7987(4)
_cell_length_b                   9.1936(3)
_cell_length_c                   27.3628(11)
_cell_measurement_reflns_used    28972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.41
_cell_measurement_theta_min      3.26
_cell_volume                     2693.04(17)
_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 V2014/5 (Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  dd29fs
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            34276
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.446
_diffrn_reflns_theta_min         3.258
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_id                dd29fs
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-3 4 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.285
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack (1983),  2259 Friedels'
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_coef       0.0040(4)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4888
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+1.8623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4790
_reflns_number_total             4888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            41557_2018_175_MOESM123_ESM.cif
_cod_data_source_block           dd29fs_sq
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               1551358
_shelx_estimated_absorpt_t_min   0.792
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              91909
_shelx_hkl_checksum              87867
_shelx_fab_checksum              69553