Regio- and Stereoselective Addition of HO/OOH to Allylic Alcohols
Wang, Xiao-Tao; Han, Wei-Bo; Chen, Hui-Jun; Zha, Qinghong; Wu, Yikang; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01280

data_4038619
_publ_section_title
;
 Regio- and Stereoselective Addition of HO/OOH to Allylic Alcohols
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01280
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H32 O5 Si'
_chemical_formula_sum            'C16 H32 O5 Si'
_chemical_formula_weight         332.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.685(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3257(3)
_cell_length_b                   7.1917(3)
_cell_length_c                   20.2080(10)
_cell_measurement_reflns_used    8403
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      55.04
_cell_measurement_theta_min      3.85
_cell_volume                     908.77(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11050
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.069
_diffrn_reflns_theta_min         3.850
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1674 before and 0.0791 after correction. The Ratio of minimum to maximum transmission is 0.7725. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0196P)^2^+0.2477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3211
_reflns_number_total             3454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01280_si_002.cif
_cod_data_source_block           mj20032_0m
_cod_database_code               4038619
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.920
_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, All O(H) groups
2. Restrained distances
 O4-H4
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              23029
_shelx_hkl_checksum              58553
_olex2_submission_special_instructions 'No special instructions were received'