Synthesis of Sulfur-Containing Exo-Bicyclic Dienes and Their Diels-Alder Reactions To Access Thiacycle-Fused Polycyclic Systems.
Castanheiro, Thomas; Schoenfelder, Angèle; Donnard, Morgan; Chataigner, Isabelle; Gulea, Mihaela; The Journal of organic chemistry 83 (2018) 4505–4515; doi:10.1021/acs.joc.8b00213

data_4034941
_publ_section_title
;
 Synthesis of Sulfur-Containing Exo-Bicyclic Dienes and Their Diels-Alder
 Reactions To Access Thiacycle-Fused Polycyclic Systems.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4505
_journal_page_last               4515
_journal_paper_doi               10.1021/acs.joc.8b00213
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H18 O3 S'
_chemical_formula_sum            'C19 H18 O3 S'
_chemical_formula_weight         326.39
_space_group_crystal_system      trigonal
_space_group_IT_number           159
_space_group_name_Hall           'P 3 -2c'
_space_group_name_H-M_alt        'P 3 1 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   17.9400(6)
_cell_length_b                   17.9400(6)
_cell_length_c                   8.4256(4)
_cell_measurement_reflns_used    4225
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.71
_cell_measurement_theta_min      4.93
_cell_volume                     2348.42(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14353
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.658
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'Cu-ImuS microfocus tube'
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0497P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.749
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                2128
_reflns_number_total             2451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00213_si_005.cif
_cod_data_source_block           jsmg170314
_cod_original_cell_volume        2348.42(19)
_cod_database_code               4034941
_shelx_estimated_absorpt_t_min   0.558
_shelx_estimated_absorpt_t_max   0.926
_shelxl_version_number           2013-4
_shelx_res_checksum              95551
_shelx_hkl_checksum              2938