Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl Peroxide.
Pilevar, Afsaneh; Hosseini, Abolfazl; Becker, Jonathan; Schreiner, Peter R.; The Journal of organic chemistry 84 (2019) 12377–12386; doi:10.1021/acs.joc.9b01748

data_4033973
_publ_section_title
;
 Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl
 Peroxide.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12377
_journal_page_last               12386
_journal_paper_doi               10.1021/acs.joc.9b01748
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C22 H26 O4'
_chemical_formula_weight         354.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                94.019(3)
_cell_angle_beta                 106.392(3)
_cell_angle_gamma                111.383(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8299(6)
_cell_length_b                   10.6683(7)
_cell_length_c                   12.3114(8)
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.65
_cell_measurement_theta_min      2.46
_cell_volume                     901.29(11)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5997
_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         31.548
_diffrn_reflns_theta_min         2.456
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.783
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.421
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0674P)^2^+0.6866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5301
_reflns_number_total             5997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01748_si_002.cif
_cod_data_source_block           D18190_tw
_cod_database_code               4033973
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              3484
_shelx_hkl_checksum              99982