#------------------------------------------------------------------------------
#$Date: 2020-03-05 02:18:52 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038033.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038033
loop_
_publ_author_name
'Saito, Fumito'
'Becker, Jonathan'
'Schreiner, Peter R.'
_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)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_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       'φ and ω 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
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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/[σ²(Fo²)+(0.0390P)²+0.2243P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.811
_shelx_estimated_absorpt_t_max   0.940
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68151(6) 0.58980(3) 0.40151(3) 0.01839(8) Uani 1 1 d . . . . .
S2 S 0.60490(5) 0.85159(3) 0.59512(3) 0.01688(7) Uani 1 1 d . . . . .
C1 C 0.59157(19) 0.75382(11) 0.41526(10) 0.01148(19) Uani 1 1 d . . . . .
C2 C 0.74630(19) 0.84564(11) 0.36840(11) 0.01172(19) Uani 1 1 d . . . . .
H2A H 0.917657 0.849857 0.403428 0.014 Uiso 1 1 calc R U . . .
H2AB H 0.730662 0.946057 0.402207 0.014 Uiso 1 1 calc R U . . .
C3 C 0.64913(18) 0.76809(11) 0.20930(10) 0.01041(18) Uani 1 1 d . . . . .
H3 H 0.742654 0.697069 0.178895 0.012 Uiso 1 1 calc R U . . .
C4 C 0.6915(2) 0.87706(12) 0.14858(11) 0.0134(2) Uani 1 1 d . . . . .
H4A H 0.862430 0.934781 0.192185 0.016 Uiso 1 1 calc R U . . .
H4AB H 0.593332 0.945151 0.173913 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6321(2) 0.81039(13) -0.00881(11) 0.0153(2) Uani 1 1 d . . . . .
H5A H 0.726032 0.879715 -0.032659 0.018 Uiso 1 1 calc R U . . .
H5AB H 0.684974 0.720689 -0.037797 0.018 Uiso 1 1 calc R U . . .
C6 C 0.3669(2) 0.77275(13) -0.09104(12) 0.0158(2) Uani 1 1 d . . . . .
H6A H 0.349578 0.738416 -0.190146 0.019 Uiso 1 1 calc R U . . .
H6AB H 0.314684 0.862731 -0.062641 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1986(2) 0.65719(12) -0.07445(11) 0.0155(2) Uani 1 1 d . . . . .
H7A H 0.251876 0.567545 -0.101539 0.019 Uiso 1 1 calc R U . . .
H7AB H 0.034817 0.633576 -0.138962 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1861(2) 0.70161(13) 0.07193(11) 0.0143(2) Uani 1 1 d . . . . .
H8A H 0.192209 0.806019 0.111764 0.017 Uiso 1 1 calc R U . . .
H8AB H 0.028681 0.645959 0.065305 0.017 Uiso 1 1 calc R U . . .
C9 C 0.38355(19) 0.67817(11) 0.17142(11) 0.01168(19) Uani 1 1 d . . . . .
H9 H 0.376351 0.572612 0.129752 0.014 Uiso 1 1 calc R U . . .
C10 C 0.3416(2) 0.71453(13) 0.31134(11) 0.0161(2) Uani 1 1 d . . . . .
H10A H 0.271325 0.797527 0.335772 0.019 Uiso 1 1 calc R U . . .
H10B H 0.232321 0.629517 0.308324 0.019 Uiso 1 1 calc R U . . .
C11 C 0.9010(2) 0.67639(14) 0.57283(12) 0.0191(2) Uani 1 1 d . . . . .
H11A H 0.959012 0.602551 0.598396 0.023 Uiso 1 1 calc R U . . .
H11B H 1.040345 0.745967 0.576374 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7787(2) 0.75594(12) 0.67175(11) 0.0157(2) Uani 1 1 d . . . . .
H12A H 0.900854 0.826083 0.761317 0.019 Uiso 1 1 calc R U . . .
H12B H 0.671671 0.685499 0.688488 0.019 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C1 94.16(5) . . ?
C12 S2 C1 98.91(5) . . ?
C2 C1 C10 101.84(8) . . ?
C2 C1 S1 111.78(7) . . ?
C10 C1 S1 110.39(8) . . ?
C2 C1 S2 113.25(7) . . ?
C10 C1 S2 112.82(7) . . ?
S1 C1 S2 106.83(5) . . ?
C1 C2 C3 105.14(8) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2AB 110.7 . . ?
C3 C2 H2AB 110.7 . . ?
H2A C2 H2AB 108.8 . . ?
C4 C3 C2 110.55(8) . . ?
C4 C3 C9 118.02(9) . . ?
C2 C3 C9 105.28(8) . . ?
C4 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C9 C3 H3 107.5 . . ?
C3 C4 C5 115.44(9) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4AB 108.4 . . ?
C5 C4 H4AB 108.4 . . ?
H4A C4 H4AB 107.5 . . ?
C6 C5 C4 114.80(9) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5AB 108.6 . . ?
C4 C5 H5AB 108.6 . . ?
H5A C5 H5AB 107.5 . . ?
C5 C6 C7 115.15(9) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6AB 108.5 . . ?
C7 C6 H6AB 108.5 . . ?
H6A C6 H6AB 107.5 . . ?
C6 C7 C8 114.59(9) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7AB 108.6 . . ?
C8 C7 H7AB 108.6 . . ?
H7A C7 H7AB 107.6 . . ?
C9 C8 C7 115.58(9) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8AB 108.4 . . ?
C7 C8 H8AB 108.4 . . ?
H8A C8 H8AB 107.4 . . ?
C8 C9 C10 111.11(9) . . ?
C8 C9 C3 117.51(9) . . ?
C10 C9 C3 104.93(8) . . ?
C8 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C3 C9 H9 107.6 . . ?
C1 C10 C9 104.67(8) . . ?
C1 C10 H10A 110.8 . . ?
C9 C10 H10A 110.8 . . ?
C1 C10 H10B 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 S1 107.39(8) . . ?
C12 C11 H11A 110.2 . . ?
S1 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
S1 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 S2 108.47(8) . . ?
C11 C12 H12A 110.0 . . ?
S2 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
S2 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.8053(12) . ?
S1 C1 1.8211(11) . ?
S2 C12 1.8173(12) . ?
S2 C1 1.8369(10) . ?
C1 C2 1.5293(14) . ?
C1 C10 1.5293(15) . ?
C2 C3 1.5409(14) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.5288(14) . ?
C3 C9 1.5699(14) . ?
C3 H3 1.0000 . ?
C4 C5 1.5345(15) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.5251(16) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.5278(16) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.5329(15) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.5244(15) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.5431(15) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5199(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
