Enantioselective [4 + 2] Cycloaddition of o-Quinone Methides and Vinyl Sulfides: Indirect Access to Generally Substituted Chiral Chromanes.
Wang, Zhaobin; Sun, Jianwei; Organic letters 19 (2017) 2334–2337; doi:10.1021/acs.orglett.7b00867

data_1556042
_publ_section_title
;
 Enantioselective [4 + 2] Cycloaddition of o-Quinone Methides and Vinyl
 Sulfides: Indirect Access to Generally Substituted Chiral Chromanes.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2334
_journal_page_last               2337
_journal_paper_doi               10.1021/acs.orglett.7b00867
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 O S'
_chemical_formula_sum            'C27 H22 O S'
_chemical_formula_weight         394.50
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.37560(5)
_cell_length_b                   8.23448(7)
_cell_length_c                   44.3104(4)
_cell_measurement_reflns_used    8259
_cell_measurement_temperature    99.94(19)
_cell_measurement_theta_max      75.4340
_cell_measurement_theta_min      5.4490
_cell_volume                     1961.41(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      99.94(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   34.50   90.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 111

  2 omega   28.00   74.50   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -30.0000 93

  3 omega   31.00   58.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000 -120.0000 54

  4 omega   43.00  137.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000 -120.0000 189

  5 omega   83.00  172.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -60.0000 179

  6 omega   95.00  174.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 159

  7 omega   48.00  121.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000  -90.0000 147

  8 omega   34.00   86.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   30.0000 105

  9 omega   34.00   87.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 107

 10 omega   30.00   98.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 137

 11 omega   25.00   94.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  120.0000 138

 12 omega   26.00  106.50   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   60.0000 161

 13 omega -130.00   47.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453    0.0000 -150.0000 354
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_orient_matrix_UB_11      -0.0861707000
_diffrn_orient_matrix_UB_12      -0.1783899000
_diffrn_orient_matrix_UB_13      -0.0008821000
_diffrn_orient_matrix_UB_21      0.2400254000
_diffrn_orient_matrix_UB_22      -0.0469744000
_diffrn_orient_matrix_UB_23      -0.0168803000
_diffrn_orient_matrix_UB_31      0.1307254000
_diffrn_orient_matrix_UB_32      -0.0312231000
_diffrn_orient_matrix_UB_33      0.0303811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            10754
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         3.991
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(4)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0232
_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^)+(0.0365P)^2^+0.4152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0602
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3486
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_cod_data_source_file            ol7b00867_si_001.cif
_cod_data_source_block           bin15cult
_cod_database_code               1556042
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36)
;
_shelx_res_checksum              81498
_shelx_hkl_checksum              46238
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-12
_olex2_submission_special_instructions 'No special instructions were received'