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_4034944
_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         'C23 H19 N3 O2 S'
_chemical_formula_sum            'C23 H19 N3 O2 S'
_chemical_formula_weight         401.47
_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'
_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                 93.0740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.68580(10)
_cell_length_b                   25.2666(4)
_cell_length_c                   8.42000(10)
_cell_measurement_reflns_used    21293
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1845.20(4)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 2003 (Spek, 2003)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24775
_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         27.487
_diffrn_reflns_theta_min         1.612
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.5985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3585
_reflns_number_total             4230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00213_si_002.cif
_cod_data_source_block           jsmg170626
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034944
_shelxl_version_number           2013-4
_shelx_res_checksum              28186
_shelx_hkl_checksum              69184