Brønsted acid-induced transannulation of the phytochemical zerumbone.
Kashiwazaki, Gengo; Watanabe, Ryo; Tsuzuki, Terutaka; Yamamoto, Chieko; Nishikawa, Atsuya; Ohtomo, Satoru; Yoshikawa, Tomomi; Kitamura, Yuto; Utaka, Yoshimi; Kawai, Yasushi; Tsuchida, Noriko; Kitayama, Takashi; Organic & biomolecular chemistry 19 (2021) 10444–10454; doi:10.1039/d1ob01634b

data_7158410
_publ_section_title
;
 Br\/onsted acid-induced transannulation of the phytochemical zerumbone.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10444
_journal_page_last               10454
_journal_paper_doi               10.1039/d1ob01634b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C16 H26 O S'
_chemical_formula_sum            'C16 H26 O S'
_chemical_formula_weight         266.44
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-03-02 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.810(15)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.525(4)
_cell_length_b                   9.518(4)
_cell_length_c                   14.178(6)
_cell_measurement_reflns_used    9678
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.02
_cell_volume                     1536.9(11)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12048
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.6738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                1996
_reflns_number_total             2782
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d1ob01634b2.cif
_cod_data_source_block           ZerSMe_S1
_cod_depositor_comments
'Adding full bibliography for 7158408--7158414.cif.'
_cod_original_cell_volume        1537.0(11)
_cod_database_code               7158410