Brønsted Acid-Catalyzed Solvent-Controlled Regioselective Hydrothiolation and Diastereoselective Cascade Cyclization of Dienes
Ji, Kai; Lu, Ka; Huang, Jie; Li, Zi-Hao; Ding, Tong-Mei; Chen, Zhi-Min; Chemical Communications  (2021) –; doi:10.1039/D1CC05383C

data_7129200
_publ_section_title
;
 Br\/onsted Acid-Catalyzed Solvent-Controlled Regioselective
 Hydrothiolation and Diastereoselective Cascade Cyclization of Dienes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05383C
_journal_year                    2021
_chemical_formula_moiety         'C18 H20 S'
_chemical_formula_sum            'C18 H20 S'
_chemical_formula_weight         268.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-08-10 deposited with the CCDC.	2021-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.856(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0653(6)
_cell_length_b                   5.67134(10)
_cell_length_c                   19.4203(4)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3310
_cell_measurement_theta_min      3.2460
_cell_volume                     3029.43(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_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    -23.00  27.00   0.50    0.05    --  -48.70  19.00  30.00  100
  2  \w    -55.00  24.00   0.50    0.05    --  -48.70  82.00 -71.00  158
  3  \w    -59.00 -29.00   0.50    0.10    -- -101.00  61.00 -60.00   60
  4  \w    -75.00 -45.00   0.50    0.10    -- -101.00  82.00 -71.00   60
  5  \w   -120.00 -88.00   0.50    0.10    -- -101.00 -45.00-150.00   64
  6  \w   -118.00 -74.00   0.50    0.05    --  -48.70-125.00-120.00   88
  7  \w   -120.00 -95.00   0.50    0.05    --  -48.70-125.00 -60.00   50
  8  \w   -120.00 -84.00   0.50    0.05    --  -48.70-125.00 -90.00   72
  9  \w   -160.00 -97.00   0.50    0.10    -- -101.00 -45.00-120.00  126
 10  \w   -173.00 -97.00   0.50    0.10    -- -101.00 -61.00-150.00  152
 11  \w    -22.00  71.00   0.50    0.05    --   48.70 -82.00 166.00  186
 12  \w     44.00 123.00   0.50    0.10    --  103.25 -82.00 166.00  158
 13  \w    139.00 177.00   0.50    0.10    --  103.25  15.00  30.00   76
 14  \w    129.00 178.00   0.50    0.10    --  103.25  30.00  60.00   98
 15  \w     89.00 167.00   0.50    0.10    --  103.25  82.00 -71.00  156
 16  \w     93.00 124.00   0.50    0.10    --  103.25  15.00  30.00   62
 17  \w     91.00 116.00   0.50    0.10    --  103.25  30.00  60.00   50
 18  \w     69.00  96.00   0.50    0.10    --  103.25 -94.00 -30.00   54
 19  \w     32.00  57.00   0.50    0.10    --  103.25 -61.00 -30.00   50
 20  \w   -159.00-129.00   0.50    0.10    -- -101.00 -82.00 166.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362910000
_diffrn_orient_matrix_UB_12      0.1590057000
_diffrn_orient_matrix_UB_13      0.0562466000
_diffrn_orient_matrix_UB_21      -0.0001946000
_diffrn_orient_matrix_UB_22      0.1744451000
_diffrn_orient_matrix_UB_23      -0.0608670000
_diffrn_orient_matrix_UB_31      -0.0426718000
_diffrn_orient_matrix_UB_32      0.1344341000
_diffrn_orient_matrix_UB_33      0.0125383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9077
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.958
_diffrn_reflns_theta_min         3.213
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0635P)^2^+1.0192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2515
_reflns_number_total             2955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05383c2.cif
_cod_data_source_block           chenzmjkw-175p
_cod_database_code               7129200
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.845
_diffrn_oxdiff_digest_frames
;
018f45d191cb2cab0e03bc33a8992db7de018800f5f
;
_diffrn_oxdiff_digest_hkl
;
014a4b4800d76f1294e5841d9c3504e893b81d
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              40366
_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 1.607
_oxdiff_exptl_absorpt_empirical_full_min 0.833