Ligand Control of Diastereodivergency in Asymmetric Inverse Electron Demand Diels–Alder Reaction
Hao, Xiaoyu; Lin, Lili; Tan, Fei; Yin, Chengkai; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 5 (2015) 6052–; doi:10.1021/acscatal.5b01719

data_4513657
_publ_section_title
;
 Ligand Control of Diastereodivergency in Asymmetric Inverse Electron
 Demand Diels--Alder Reaction
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6052
_journal_paper_doi               10.1021/acscatal.5b01719
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C29 H27 N O6 S'
_chemical_formula_sum            'C29 H27 N O6 S'
_chemical_formula_weight         517.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1813(6)
_cell_length_b                   12.9222(5)
_cell_length_c                   16.9425(7)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0050
_cell_measurement_theta_min      3.5380
_cell_volume                     2666.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details
;
  1 omega  -66.00   50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174    0.0000 -120.0000 116

  2 omega   11.00   39.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  -99.0000 -150.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0216585000
_diffrn_orient_matrix_UB_12      0.0434107000
_diffrn_orient_matrix_UB_13      0.0203511000
_diffrn_orient_matrix_UB_21      0.0536837000
_diffrn_orient_matrix_UB_22      0.0140690000
_diffrn_orient_matrix_UB_23      0.0121286000
_diffrn_orient_matrix_UB_31      0.0060136000
_diffrn_orient_matrix_UB_32      0.0305652000
_diffrn_orient_matrix_UB_33      -0.0345110000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8091
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.968
_diffrn_reflns_theta_min         3.153
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1088
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0449P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.726
_reflns_number_gt                3580
_reflns_number_total             5715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b01719_si_003.cif
_cod_data_source_block           140428_s3_hxy
_cod_database_code               4513657
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c8h12n4o2s1
_reflns_odcompleteness_completeness 99.61
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C24(H24), C25(H25), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              67026
_shelx_hkl_checksum              67808