Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.
Dang, Hang T.; Nguyen, Vu T.; Nguyen, Viet D.; Arman, Hadi D.; Larionov, Oleg V.; Organic & biomolecular chemistry 16 (2018) 3605–3609; doi:10.1039/c8ob00745d

data_7156218
_publ_section_title
;
 Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes
 enabled by sodium metabisulfite as a sulfur dioxide equivalent.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3605
_journal_page_last               3609
_journal_paper_doi               10.1039/c8ob00745d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C13 H16 O3 S'
_chemical_formula_sum            'C13 H16 O3 S'
_chemical_formula_weight         252.32
_chemical_name_systematic
3-(2-Hydroxy-2-phenylethyl)-4-methyl-2,5-dihydrothiophene-1,1-dioxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.262(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4091(3)
_cell_length_b                   7.52720(10)
_cell_length_c                   13.3823(3)
_cell_measurement_reflns_used    9347
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      3.0410
_cell_volume                     1231.41(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -39.00  80.00   1.00   60.00    --   -9.60  27.00  86.00  119
  2  \w    -99.00  20.00   1.00   60.00    --   -9.60 -27.00 -76.00  119
  3  \w    -99.00  15.00   1.00   60.00    --   -9.60 -38.00 150.00  114
  4  \w    -42.00  80.00   1.00   60.00    --   -9.60  72.00 150.00  122
  5  \w    -39.00  80.00   1.00   60.00    --   -9.60  57.00 -90.00  119
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0324514000
_diffrn_orient_matrix_UB_12      -0.0274454000
_diffrn_orient_matrix_UB_13      -0.0544926000
_diffrn_orient_matrix_UB_21      0.0166096000
_diffrn_orient_matrix_UB_22      -0.0891948000
_diffrn_orient_matrix_UB_23      0.0147226000
_diffrn_orient_matrix_UB_31      -0.0451465000
_diffrn_orient_matrix_UB_32      -0.0130718000
_diffrn_orient_matrix_UB_33      0.0138881000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
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    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.094
_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     156
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0480P)^2^+2.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             2549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00745d2.cif
_cod_data_source_block           cd1645
_cod_depositor_comments          'Adding full bibliography for 7156218.cif.'
_cod_database_code               7156218
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 88.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.92
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.108
_oxdiff_exptl_absorpt_empirical_full_min 0.841