Monocationic Cinchoninium Catalyzed Asymmetric Oxohydroxylation of Enoates
Li, Shuangqing; Wang, Shuangshuang; Li, Juan; Qi, Yue; Wang, Chao; Zong, Lili; Tan, Choon-Hong; ACS Catalysis 11 (2021) 15141–15148; doi:10.1021/acscatal.1c04849

data_4519250
_publ_section_title
;
 Monocationic Cinchoninium Catalyzed Asymmetric Oxohydroxylation of
 Enoates
;
_journal_issue                   24
_journal_name_full               'ACS Catalysis'
_journal_page_first              15141
_journal_page_last               15148
_journal_paper_doi               10.1021/acscatal.1c04849
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 N2 O5 S'
_chemical_formula_sum            'C13 H18 N2 O5 S'
_chemical_formula_weight         314.35
_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             2021-01-11
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.255(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2089(14)
_cell_length_b                   6.4415(5)
_cell_length_c                   15.8188(13)
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.7070
_cell_measurement_theta_min      2.6770
_cell_volume                     1508.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -78.00 -39.00   1.00    5.50    --  -11.27 -57.00 -60.00   39
  2  \w    -69.00   3.00   1.00    5.50    --  -11.27 -57.00 -30.00   72
  3  \w    -33.00  61.00   1.00    5.50    --  -11.27  57.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205940000
_diffrn_orient_matrix_UB_12      0.0036597000
_diffrn_orient_matrix_UB_13      0.0449629000
_diffrn_orient_matrix_UB_21      -0.0428035000
_diffrn_orient_matrix_UB_22      -0.0148842000
_diffrn_orient_matrix_UB_23      0.0098225000
_diffrn_orient_matrix_UB_31      0.0064843000
_diffrn_orient_matrix_UB_32      -0.1090936000
_diffrn_orient_matrix_UB_33      0.0001830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8384
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.734
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.419
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6121
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.1832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.569
_reflns_Friedel_fraction_full    0.790
_reflns_Friedel_fraction_max     0.581
_reflns_number_gt                4991
_reflns_number_total             6121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04849_si_002.cif
_cod_data_source_block           5064-1
_cod_database_code               4519250
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), N4(H4), C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C)
2.c Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              25764
_shelx_hkl_checksum              76736
_olex2_date_sample_data_collection 2021-01-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.853