Enantioselective addition of selenosulfonates to α,β-unsaturated ketones.
Luo, Shilong; Zhang, Nan; Wang, Zhen; Yan, Hailong; Organic & biomolecular chemistry 16 (2018) 2893–2901; doi:10.1039/c8ob00359a

data_7156168
_publ_section_title
;
 Enantioselective addition of selenosulfonates to \a,\b-unsaturated
 ketones.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2893
_journal_page_last               2901
_journal_paper_doi               10.1039/c8ob00359a
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H33 Br O4 S Se'
_chemical_formula_sum            'C33 H33 Br O4 S Se'
_chemical_formula_weight         684.52
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.199(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9327(4)
_cell_length_b                   18.8397(9)
_cell_length_c                   22.3499(16)
_cell_measurement_reflns_used    4051
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7280
_cell_measurement_theta_min      3.5880
_cell_volume                     3287.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.958
_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    -82.00 -52.00   0.60   22.50    --  -14.97-178.00 -90.00   50
  2  \w    -79.00   3.20   0.60   22.50    --  -14.97 -38.00-120.00  137
  3  \w    -32.00  -5.00   0.60   22.50    --  -14.97  57.00  60.00   45
  4  \w      9.00  47.40   0.60   22.50    --  -14.97  57.00  60.00   64
  5  \w     -5.00  22.00   0.60   22.50    --  -14.97 -99.00-180.00   45
  6  \w     40.00  64.60   0.60   22.50    --   16.69 178.00 -30.00   41
  7  \w      4.00  36.40   0.60   22.50    --   16.53  77.00-120.00   54
  8  \w      6.00  19.80   0.60   22.50    --   16.53  77.00 150.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0039989000
_diffrn_orient_matrix_UB_12      0.0277756000
_diffrn_orient_matrix_UB_13      0.0216214000
_diffrn_orient_matrix_UB_21      -0.0078595000
_diffrn_orient_matrix_UB_22      0.0254021000
_diffrn_orient_matrix_UB_23      -0.0237462000
_diffrn_orient_matrix_UB_31      -0.0904582000
_diffrn_orient_matrix_UB_32      -0.0009824000
_diffrn_orient_matrix_UB_33      -0.0027180000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19444
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.981
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     699
_refine_ls_number_reflns         10418
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+5.9542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.608
_reflns_Friedel_fraction_max     0.582
_reflns_number_gt                6712
_reflns_number_total             10418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00359a2.cif
_cod_data_source_block           180125_s4_wz
_cod_depositor_comments          'Adding full bibliography for 7156168.cif.'
_cod_database_code               7156168
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.579
_shelx_estimated_absorpt_t_min   0.480
_reflns_odcompleteness_completeness 95.79
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C19
 2.5 with sigma of 0.02
 C17-C18
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C50) = Uanis(C51) = Uanis(C52)
Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C33)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C40(H40), C42(H42)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C41(H41A,H41B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14),
 C15(H15), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31),
  C32(H32), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C44(H44),
 C45(H45), C47(H47), C48(H48), C55(H55), C56(H56), C58(H58), C59(H59), C61(H61),
  C62(H62), C64(H64), C65(H65)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C33(H33A,H33B,
 H33C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C66(H66A,
 H66B,H66C)
;
_shelx_res_checksum              93131
_olex2_date_sample_data_collection 2018-01-25
_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 2.266
_oxdiff_exptl_absorpt_empirical_full_min 0.623