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_4034872
_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             2018-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.58390(10)
_cell_length_b                   12.70300(10)
_cell_length_c                   24.8305(3)
_cell_measurement_reflns_used    24315
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6870
_cell_measurement_theta_min      3.9110
_cell_volume                     3022.97(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -72.00 -14.00   1.00    1.00    --  -37.04 -19.00 150.00   58
  2  \w    -88.00 -61.00   1.00    1.00    --  -37.04 125.00-180.00   27
  3  \w    -80.00 -18.00   1.00    1.00    --  -37.04 -38.00 -90.00   62
  4  \w     10.00  46.00   1.00    1.00    --   37.04  77.00-180.00   36
  5  \w     52.00  93.00   1.00    1.00    --   37.04  77.00 150.00   41
  6  \w     38.00  99.00   1.00    1.00    --   37.04  57.00  90.00   61
  7  \w      4.00  36.00   1.00    1.00    --   37.04 -99.00-150.00   32
  8  \w      1.00  76.00   1.00    1.00    --   37.04 -99.00  30.00   75
  9  \w     56.00 103.00   1.00    1.00    --   37.04  57.00 -90.00   47
 10  \w     41.00  77.00   1.00    1.00    --   37.04-125.00  30.00   36
 11  \w     71.00 105.00   1.00    1.00    --   37.04  77.00-180.00   34
 12  \w     60.00  85.00   1.00    1.00    --   37.04  77.00 -90.00   25
 13  \w     24.00  51.00   1.00    1.00    --   37.04  77.00 -90.00   27
 14  \w     51.00  78.00   1.00    1.00    --   37.04-125.00-150.00   27
 15  \w     42.00  76.00   1.00    1.00    --   37.04 -99.00-150.00   34
 16  \w     21.00 103.00   1.00    1.00    --   37.04  57.00 120.00   82
 17  \w     58.00 106.00   1.00    1.00    --   37.04  38.00   0.00   48
 18  \w     22.00  57.00   1.00    1.00    --   37.04  38.00   0.00   35
 19  \w     51.00  76.00   1.00    1.00    --   37.04 -99.00-180.00   25
 20  \w     43.00 129.00   1.00    2.00    --  111.00 -38.00  30.00   86
 21  \w     67.00 110.00   1.00    2.00    --  111.00-111.00   0.00   43
 22  \w     69.00 113.00   1.00    2.00    --  111.00-111.00 120.00   44
 23  \w     99.00 137.00   1.00    2.00    --  111.00  50.00  60.00   38
 24  \w    138.00 165.00   1.00    2.00    --  111.00  38.00   0.00   27
 25  \w     91.00 125.00   1.00    2.00    --  111.00 -25.00 -30.00   34
 26  \w     42.00 136.00   1.00    2.00    --  111.00 -25.00  90.00   94
 27  \w     73.00 120.00   1.00    2.00    --  111.00 -64.00  30.00   47
 28  \w     86.00 113.00   1.00    2.00    --  111.00 -77.00 -30.00   27
 29  \w    143.00 170.00   1.00    2.00    --  111.00  12.00  30.00   27
 30  \w     44.00  69.00   1.00    2.00    --  111.00-111.00  30.00   25
 31  \w     49.00  76.00   1.00    2.00    --  111.00 -25.00 -30.00   27
 32  \w     93.00 131.00   1.00    2.00    --  111.00  38.00   0.00   38
 33  \w     73.00 100.00   1.00    2.00    --  111.00 -69.00 103.94   27
 34  \w    104.00 166.00   1.00    2.00    --  111.00 111.00 150.00   62
 35  \w     83.00 109.00   1.00    2.00    --  111.00 -77.00 -90.00   26
 36  \w     45.00  70.00   1.00    2.00    --  111.00-111.00-180.00   25
 37  \w    151.00 176.00   1.00    2.00    --  111.00 111.00-180.00   25
 38  \w    108.00 141.00   1.00    2.00    --  111.00  64.00 -60.00   33
 39  \w     58.00  89.00   1.00    2.00    --  111.00 -50.00   0.00   31
 40  \w    118.00 177.00   1.00    2.00    --  111.00  77.00  90.00   59
 41  \w    153.00 178.00   1.00    2.00    --  111.00  64.00 -60.00   25
 42  \w     53.00  78.00   1.00    2.00    --  111.00 -77.00 -90.00   25
 43  \w    106.00 131.00   1.00    2.00    --  111.00 -71.00 111.25   25
 44  \w     81.00 111.00   1.00    2.00    --  111.00-111.00  90.00   30
 45  \w     55.00  86.00   1.00    2.00    --  111.00 -50.00 -90.00   31
 46  \w     78.00 134.00   1.00    2.00    --  111.00   0.00 -30.00   56
 47  \w    100.00 176.00   1.00    2.00    --  111.00 111.00  60.00   76
 48  \w    109.00 134.00   1.00    2.00    --  111.00  77.00 120.00   25
 49  \w    110.00 177.00   1.00    2.00    --  111.00  25.00 150.00   67
 50  \w     57.00  94.00   1.00    2.00    --  111.00 -77.00 150.00   37
 51  \w     42.00  70.00   1.00    2.00    --  111.00 -92.00   0.00   28
 52  \w     86.00 113.00   1.00    2.00    --  111.00-111.00 -60.00   27
 53  \w     55.00  80.00   1.00    2.00    --  111.00 -50.00 120.00   25
 54  \w     89.00 127.00   1.00    2.00    --  111.00 -50.00 120.00   38
 55  \w     57.00 113.00   1.00    2.00    --  111.00-111.00-150.00   56
 56  \w     50.00  95.00   1.00    2.00    --  111.00 -77.00-120.00   45
 57  \w    127.00 167.00   1.00    2.00    --  111.00  38.00-180.00   40
 58  \w     87.00 114.00   1.00    2.00    --  111.00  12.00  30.00   27
 59  \w     68.00 111.00   1.00    2.00    --  111.00-111.00 -90.00   43
 60  \w     43.00  68.00   1.00    2.00    --  111.00 -92.00 -90.00   25
 61  \w     84.00 109.00   1.00    2.00    --  111.00 -92.00 -90.00   25
 62  \w     65.00  90.00   1.00    2.00    --  111.00 -92.00 -60.00   25
 63  \w     42.00  69.00   1.00    2.00    --  111.00-111.00 150.00   27
 64  \w     43.00  68.00   1.00    2.00    --  111.00-111.00-120.00   25
 65  \w     53.00 109.00   1.00    2.00    --  111.00 -92.00 150.00   56
 66  \w     73.00  98.00   1.00    2.00    --  111.00 -92.00 -30.00   25
 67  \w     94.00 129.00   1.00    2.00    --  111.00  50.00  30.00   35
 68  \w    136.00 178.00   1.00    2.00    --  111.00  50.00  30.00   42
 69  \w     58.00  85.00   1.00    2.00    --  111.00 -50.00  30.00   27
 70  \w     46.00  71.00   1.00    2.00    --  111.00 -64.00-120.00   25
 71  \w     88.00 113.00   1.00    2.00    --  111.00-111.00  30.00   25
 72  \w     97.00 130.00   1.00    2.00    --  111.00 -73.00 -65.95   33
 73  \w    104.00 129.00   1.00    2.00    --  111.00 -41.00 119.42   25
 74  \w     89.00 125.00   1.00    2.00    --  111.00 -77.00-180.00   36
 75  \w     64.00  89.00   1.00    2.00    --  111.00 -41.00 119.42   25
;
_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      -0.0206304000
_diffrn_orient_matrix_UB_12      0.0287175000
_diffrn_orient_matrix_UB_13      0.0597445000
_diffrn_orient_matrix_UB_21      -0.1491027000
_diffrn_orient_matrix_UB_22      -0.0451495000
_diffrn_orient_matrix_UB_23      -0.0020181000
_diffrn_orient_matrix_UB_31      0.0564424000
_diffrn_orient_matrix_UB_32      -0.1088213000
_diffrn_orient_matrix_UB_33      0.0166123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.848
_diffrn_reflns_theta_min         3.560
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81845
_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    1.109
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0849P)^2^+0.2234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6001
_reflns_number_total             6097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02626_si_003.cif
_cod_data_source_block           tf-7-39B_scale
_cod_database_code               4034872
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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), C51(H67), C53(H66), C61(H61)
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), C54(H54A,H54B), C56(H56A,H56B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C68(H68A,H68B), C69(H69A,H69B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C62(H62A,H62B,
 H62C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C)
;
_shelx_res_checksum              84695
_shelx_hkl_checksum              59634
_ins_header
;
TITL tf-7-39B_scale in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   9.583868  12.703020  24.830453  90.0000  90.0000  90.0000
ZERR    8.00   0.000114   0.000144   0.000305   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 128.00 224.00 16.00
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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.557