Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls.
Giarrusso, James; Do, Dung T.; Johnson, Jeffrey S.; Organic letters 19 (2017) 3107–3110; doi:10.1021/acs.orglett.7b01225

data_1546166
_publ_section_title
;
 Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic
 Endoperoxidation of Polycarbonyls.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3107
_journal_page_last               3110
_journal_paper_doi               10.1021/acs.orglett.7b01225
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C15 H22 O6'
_chemical_formula_sum            'C15 H22 O6'
_chemical_formula_weight         298.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.692(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9990(6)
_cell_length_b                   9.8330(6)
_cell_length_c                   17.8989(11)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.07
_cell_measurement_theta_min      4.50
_cell_volume                     1550.96(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14553
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.183
_diffrn_reflns_theta_min         5.019
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.9312
_exptl_absorpt_correction_T_min  0.8557
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0501 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9189.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.5813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2790
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01225_si_003.cif
_cod_data_source_block           x1602011
_cod_depositor_comments
'Adding full bibliography for 1546165--1546167.cif.'
_cod_database_code               1546166
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47998
_shelx_hkl_checksum              440
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'