Asymmetric tandem reactions of N-sulfonylimines and α,β-unsaturated aldehydes: an alternative reaction pathway to that of using saturated aldehydes
An, Qianjin; Li, Jing; Shen, Jiefeng; Butt, Nicholas; Liu, Delong; Liu, Yangang; Zhang, Wanbin; Chemical Communications (Cambridge, United Kingdom) 51 (2015) 885–888; doi:10.1039/c4cc07051h

data_7116313
_publ_section_title
;
 Asymmetric tandem reactions of N-sulfonylimines and \a,\b-unsaturated
 aldehydes: an alternative reaction pathway to that of using saturated
 aldehydes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   5
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              885
_journal_page_last               888
_journal_paper_doi               10.1039/c4cc07051h
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 Cl N O3 S'
_chemical_formula_sum            'C17 H14 Cl N O3 S'
_chemical_formula_weight         347.80
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-07-23 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.699(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7401(4)
_cell_length_b                   14.0157(10)
_cell_length_c                   14.8926(10)
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5158
_cell_measurement_theta_min      2.9251
_cell_volume                     1614.88(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0124289000
_diffrn_orient_matrix_UB_12      0.0280087000
_diffrn_orient_matrix_UB_13      0.0389339000
_diffrn_orient_matrix_UB_21      0.0003091000
_diffrn_orient_matrix_UB_22      0.0420118000
_diffrn_orient_matrix_UB_23      -0.0265814000
_diffrn_orient_matrix_UB_31      -0.0908279000
_diffrn_orient_matrix_UB_32      -0.0036563000
_diffrn_orient_matrix_UB_33      -0.0068297000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6811
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack (1983), 1983 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1076P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                3580
_reflns_number_total             5063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07051h2.cif
_cod_data_source_block           140707_aqj_0707
_cod_original_cell_volume        1614.89(18)
_cod_database_code               7116313
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 Cl1'
_reflns_odcompleteness_completeness 99.57
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C26(H26), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C31(H31), C32(H32),
  C33(H33), C34(H34)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;