Enantioselective Approach to Polycyclic Polyprenylated Acylphloroglucinols via Catalytic Asymmetric Intramolecular Cyclopropanation.
Uetake, Yuta; Uwamori, Masahiro; Nakada, Masahisa; The Journal of organic chemistry 80 (2015) 1735–1745; doi:10.1021/jo5026699

data_4030592
_publ_section_title
;
 Enantioselective Approach to Polycyclic Polyprenylated
 Acylphloroglucinols via Catalytic Asymmetric Intramolecular
 Cyclopropanation.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1735
_journal_page_last               1745
_journal_paper_doi               10.1021/jo5026699
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C17 H18 O6 S'
_chemical_formula_sum            'C17 H18 O6 S'
_chemical_formula_weight         350.39
_space_group_IT_number           19
_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                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.68(2)
_cell_length_b                   19.14(3)
_cell_length_c                   6.208(12)
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.70
_cell_volume                     1507(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15063
_diffrn_reflns_theta_full        27.20
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736.00
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.139
_refine_diff_density_max         1.01
_refine_diff_density_min         -1.01
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1397 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2489
_reflns_number_gt                2302
_reflns_number_total             3339
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5026699_si_001.cif
_cod_data_source_block           SX211
_cod_depositor_comments
'Adding full bibliography for 4030592--4030593.cif.'
_cod_database_code               4030592