Synthesis and Conformational Analysis of Parent Perhydroazulenes Reveals an Energetically Preferred cis Ring Fusion.
Saito, Fumito; Becker, Jonathan; Schreiner, Peter R.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00167

data_4038033
_publ_section_title
;
 Synthesis and Conformational Analysis of Parent Perhydroazulenes Reveals
 an Energetically Preferred cis Ring Fusion.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00167
_journal_year                    2020
_chemical_formula_sum            'C12 H20 S2'
_chemical_formula_weight         228.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                112.0266(17)
_cell_angle_beta                 103.9938(19)
_cell_angle_gamma                99.262(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9709(3)
_cell_length_b                   10.3213(5)
_cell_length_c                   11.0614(6)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.22
_cell_volume                     588.69(5)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
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_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33917
_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         31.503
_diffrn_reflns_theta_min         2.217
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0390P)^2^+0.2243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3324
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00167_si_002.cif
_cod_data_source_block           D19103
_cod_database_code               4038033
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.811
_shelx_estimated_absorpt_t_max   0.940
_shelx_res_checksum              83983
_shelx_hkl_checksum              51306