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_4034943
_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         'C14 H16 O4 S'
_chemical_formula_sum            'C14 H16 O4 S'
_chemical_formula_weight         280.33
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.9030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1274(3)
_cell_length_b                   17.4435(7)
_cell_length_c                   8.9072(4)
_cell_measurement_reflns_used    8199
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.01
_cell_measurement_theta_min      2.58
_cell_volume                     1225.78(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
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_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23107
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.027
_diffrn_reflns_theta_min         2.335
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
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_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0534P)^2^+0.5297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1094
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_reflns_number_gt                3771
_reflns_number_total             4631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00213_si_004.cif
_cod_data_source_block           jsmg170425
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034943
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.958
_shelxl_version_number           2013-4
_shelx_res_checksum              34734
_shelx_hkl_checksum              8765