Dithiane Induced Cycloaddition/Aromatization Tactic for the Synthesis of Multisubstituted Furans.
Lai, Junshan; Liang, Yongping; Liu, Teng; Tang, Shouchu; Organic letters 18 (2016) 2066–2069; doi:10.1021/acs.orglett.6b00699

data_1555533
_publ_section_title
;
 Dithiane Induced Cycloaddition/Aromatization Tactic for the Synthesis of
 Multisubstituted Furans.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2066
_journal_page_last               2069
_journal_paper_doi               10.1021/acs.orglett.6b00699
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H20 O2 S2'
_chemical_formula_sum            'C20 H20 O2 S2'
_chemical_formula_weight         356.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-22
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.111(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3493(5)
_cell_length_b                   16.6118(5)
_cell_length_c                   11.4274(6)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      26.4930
_cell_measurement_theta_min      3.7910
_cell_volume                     1764.10(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    6.00   87.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  120.0000 54

  2 omega   19.00   61.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -180.0000 28

  3 omega  -47.00   58.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  120.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0457811000
_diffrn_orient_matrix_UB_12      0.0065837000
_diffrn_orient_matrix_UB_13      0.0304935000
_diffrn_orient_matrix_UB_21      -0.0595659000
_diffrn_orient_matrix_UB_22      0.0044611000
_diffrn_orient_matrix_UB_23      -0.0619807000
_diffrn_orient_matrix_UB_31      -0.0135143000
_diffrn_orient_matrix_UB_32      -0.0419568000
_diffrn_orient_matrix_UB_33      -0.0017609000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7206
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.2037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                2500
_reflns_number_total             3469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00699_si_002.cif
_cod_data_source_block           tshch_0521_1
_cod_original_cell_volume        1764.11(14)
_cod_database_code               1555533
_reflns_odcompleteness_completeness 99.76
_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:
 C10(H10a,H10b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C12(H12), C13(H13), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_date_sample_data_collection 2015-05-21
_olex2_submission_special_instructions 'No special instructions were received'