Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis.
Liffert, Raphael; Linden, Anthony; Gademann, Karl; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b10053

data_4126670
_publ_section_title
;
 Total Synthesis of the Sesquiterpenoid Periconianone A Based on a
 Postulated Biogenesis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b10053
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H38 O3 Si'
_chemical_formula_sum            'C22 H38 O3 Si'
_chemical_formula_weight         378.61
_chemical_melting_point          434.3
_chemical_name_systematic
;
(3R,4aR,5R,6R)-3-((R)-but-3-en-2-yl)-6-((tert-butyldimethylsilyl)oxy)-
3-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.354(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.2644(6)
_cell_length_b                   7.33538(18)
_cell_length_c                   12.3638(3)
_cell_measurement_reflns_used    5160
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      73.3120
_cell_measurement_theta_min      3.5690
_cell_volume                     2284.70(10)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_collection
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2016 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle \k-geometry diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11790
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0800P)^2^+0.5017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                4108
_reflns_number_total             4406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10053_si_003.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126670
_shelx_shelxl_version_number     2016/6
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_oxdiff_exptl_absorpt_empirical_full_max 1.419
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              62329
_shelx_hkl_checksum              99002