Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium.
Wang, Chao; Zong, Lili; Tan, Choon-Hong; Journal of the American Chemical Society  (2015) 150813122746001–; doi:10.1021/jacs.5b05792

data_4124403
_publ_section_title
;
 Enantioselective Oxidation of Alkenes with Potassium Permanganate
 Catalyzed by Chiral Dicationic Bisguanidinium.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              150813122746001
_journal_paper_doi               10.1021/jacs.5b05792
_journal_year                    2015
_chemical_formula_sum            'C15 H22 O5'
_chemical_formula_weight         282.32
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                96.538(4)
_cell_angle_beta                 102.138(4)
_cell_angle_gamma                90.841(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8957(9)
_cell_length_b                   10.6844(16)
_cell_length_c                   12.4428(19)
_cell_measurement_reflns_used    9701
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.50
_cell_measurement_theta_min      3.66
_cell_volume                     760.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30349
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.498
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'Sealed Microfocusing Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7425
_exptl_absorpt_correction_T_min  0.5587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
; 
 Flack x determined using 2567 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.21(5)
_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     387
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0994P)^2^+0.2782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                5446
_reflns_number_total             5520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05792_si_001.cif
_cod_data_source_block           F056
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               4124403
_shelxl_version_number           2014/6
_shelx_res_checksum              32315
_shelx_hkl_checksum              33998