Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework.
Tang, Fei; Lan, Ping; Bolte, Benoit; Banwell, Martin G.; Ward, Jas S.; Willis, Anthony C.; The Journal of organic chemistry 83 (2018) 14049–14056; doi:10.1021/acs.joc.8b02626

data_4034873
_publ_section_title
;
 Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene
 Embodying the Decahydrocyclobuta[ d]indene Framework.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14049
_journal_page_last               14056
_journal_paper_doi               10.1021/acs.joc.8b02626
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H28 O2'
_chemical_formula_sum            'C16 H28 O2'
_chemical_formula_weight         252.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3617(2)
_cell_length_b                   8.7528(2)
_cell_length_c                   26.7339(7)
_cell_measurement_reflns_used    3940
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6600
_cell_measurement_theta_min      5.2940
_cell_volume                     1488.62(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     26.00  90.00   1.00    7.00    --   37.04-125.00 -60.00   64
  2  \w    -30.00  49.00   1.00    7.00    --   37.04 -57.00 120.00   79
  3  \w    -33.00  56.00   1.00    7.00    --   37.04 -19.00-150.00   89
  4  \w     18.00 106.00   1.00    7.00    --   37.04  38.00  30.00   88
  5  \w     30.00  83.00   1.00    7.00    --   37.04-125.00  90.00   53
  6  \w     21.00 100.00   1.00    7.00    --   37.04  38.00-120.00   79
  7  \w     49.00 110.00   1.00   40.00    --  111.00 -50.00 -60.00   61
  8  \w     62.00 112.00   1.00   40.00    --  111.00-111.00-150.00   50
  9  \w     82.00 109.00   1.00   40.00    --  111.00 -92.00  60.00   27
 10  \w     94.00 169.00   1.00   40.00    --  111.00  50.00  60.00   75
 11  \w     43.00 128.00   1.00   40.00    --  111.00 -50.00  60.00   85
 12  \w     73.00 107.00   1.00   40.00    --  111.00 -92.00 -60.00   34
 13  \w     48.00 107.00   1.00   40.00    --  111.00 -92.00-120.00   59
 14  \w     54.00 122.00   1.00   40.00    --  111.00 -25.00   0.00   68
 15  \w    101.00 173.00   1.00   40.00    --  111.00  50.00 -60.00   72
 16  \w    123.00 178.00   1.00   40.00    --  111.00  77.00 -30.00   55
 17  \w     92.00 118.00   1.00   40.00    --  111.00  77.00 -30.00   26
 18  \w     86.00 113.00   1.00   40.00    --  111.00-111.00  30.00   27
 19  \w     43.00 127.00   1.00   40.00    --  111.00 -50.00-150.00   84
 20  \w     44.00  80.00   1.00   40.00    --  111.00 -92.00  60.00   36
 21  \w    104.00 178.00   1.00   40.00    --  111.00  64.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0219968000
_diffrn_orient_matrix_UB_12      0.1690740000
_diffrn_orient_matrix_UB_13      -0.0151199000
_diffrn_orient_matrix_UB_21      -0.1000950000
_diffrn_orient_matrix_UB_22      -0.0486143000
_diffrn_orient_matrix_UB_23      -0.0499940000
_diffrn_orient_matrix_UB_31      -0.2194368000
_diffrn_orient_matrix_UB_32      0.0051739000
_diffrn_orient_matrix_UB_33      0.0243341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.776
_diffrn_reflns_theta_min         5.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0692P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2649
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02626_si_004.cif
_cod_data_source_block           tf-7-39A_scale
_cod_database_code               4034873
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H17), C3(H16), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C18(H18A,
 H18B), C19(H19A,H19B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              92020
_shelx_hkl_checksum              78671
_ins_header
;
TITL tf-7-39A_scale in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   6.361745   8.752844  26.733859  90.0000  90.0000  90.0000
ZERR    4.00   0.000164   0.000226   0.000740   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H O
UNIT 64.00 112.00 8.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.828