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_1546165
_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         'C16 H24 O7'
_chemical_formula_sum            'C16 H24 O7'
_chemical_formula_weight         328.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                92.003(2)
_cell_angle_beta                 93.9208(19)
_cell_angle_gamma                101.502(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8731(4)
_cell_length_b                   11.2643(4)
_cell_length_c                   14.1668(4)
_cell_measurement_reflns_used    9024
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.431
_cell_measurement_theta_min      3.131
_cell_volume                     1694.20(10)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21541
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.639
_diffrn_reflns_theta_max         66.639
_diffrn_reflns_theta_min         3.131
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.8752
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8932.
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    1.287
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0477P)^2^+0.6123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4719
_reflns_number_total             5788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01225_si_002.cif
_cod_data_source_block           x1603003
_cod_depositor_comments
'Adding full bibliography for 1546165--1546167.cif.'
_cod_database_code               1546165
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.852
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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), C15(H15), C21(H21), C36(H36), C37(H37), C45(H45), C51(H51)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C32(H32A,H32B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C46(H46A,
 H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C52(H52A,H52B,H52C),
 C53(H53A,H53B,H53C)
;
_shelx_res_checksum              87256
_shelx_hkl_checksum              82435
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'