Stereoselective Total Syntheses of Acutifolone A, Bisacutifolone A and B, Pinguisenol, and Isonaviculol.
Yadav, Jhillu Singh; Singh, Shweta; Das, Saibal; ACS omega 3 (2018) 636–647; doi:10.1021/acsomega.7b01513

data_4515915
_publ_section_title
;
 Stereoselective Total Syntheses of Acutifolone A, Bisacutifolone A and B,
 Pinguisenol, and Isonaviculol.
;
_journal_issue                   1
_journal_name_full               'ACS omega'
_journal_page_first              636
_journal_page_last               647
_journal_paper_doi               10.1021/acsomega.7b01513
_journal_volume                  3
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C13 H18 O3'
_chemical_formula_moiety         'C13 H18 O3'
_chemical_formula_structural     'C13 H18 O3'
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.27
_chemical_name_systematic
;
Methyl (1a<i>S</i>,4a<i>R</i>,5<i>R</i>,7a<i>R</i>)-5-methyl-2-oxo-
octahydrocyclopropa[<i>d</i>]indene- 4a-carboxylate
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1234(17)
_cell_length_b                   7.7506(19)
_cell_length_c                   21.457(10)
_cell_measurement_reflns_used    946
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0338
_cell_measurement_theta_min      3.0194
_cell_volume                     1184.7(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
'PLATON (Spek, 2003) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details
;
  1 omega   38.00   84.00   1.0000   39.2200
omega____ theta____ kappa____ phi______ frames
    -       19.9670  178.0000  150.0000 46

  2 omega  -24.00    3.00   1.0000   39.2200
omega____ theta____ kappa____ phi______ frames
    -       19.9670  -57.0000  -30.0000 27

  3 omega  -53.00   29.00   1.0000   39.2200
omega____ theta____ kappa____ phi______ frames
    -       19.9670  -38.0000 -150.0000 82

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0996777000
_diffrn_orient_matrix_UB_12      0.0022289000
_diffrn_orient_matrix_UB_13      -0.0006187000
_diffrn_orient_matrix_UB_21      -0.0015560000
_diffrn_orient_matrix_UB_22      -0.0580743000
_diffrn_orient_matrix_UB_23      -0.0257325000
_diffrn_orient_matrix_UB_31      -0.0017109000
_diffrn_orient_matrix_UB_32      -0.0708006000
_diffrn_orient_matrix_UB_33      0.0205872000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.8189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.074(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.1243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                1766
_reflns_number_total             2485
_reflns_threshold_expression     I>2\s(I)
_publcif_datablock.id            {8c0e47cd-cdd5-44d5-a02a-712442bdc10e}
_cod_data_source_file            ao7b01513_si_002.cif
_cod_data_source_block           exp_4391
_cod_original_cell_volume        1184.6(7)
_cod_database_code               4515915