Enantioselective Synthesis of the 5-6-7 Carbocyclic Core of the Gagunin Diterpenoids
Shibuya, Grant M.; Enquist, John A., Jr.; Stoltz, Brian M.; Organic Letters 15 (2013) 3480–3483; doi:10.1021/ol401514s

data_1547480
_publ_section_title
;
 Enantioselective Synthesis of the 5-6-7 Carbocyclic Core of the Gagunin
 Diterpenoids
;
_journal_name_full               'Organic Letters'
_journal_page_first              3480
_journal_page_last               3483
_journal_paper_doi               10.1021/ol401514s
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.36
_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'
_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     dual
_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                   7.1115(3)
_cell_length_b                   8.2413(4)
_cell_length_c                   26.0740(11)
_cell_measurement_reflns_used    7790
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.49
_cell_measurement_theta_min      2.59
_cell_volume                     1528.15(12)
_computing_cell_refinement       'SAINT V8.18C (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2012.2-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.18C (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
 and SHELXTL (Bruker-AXS, 2007) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            31815
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.19
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker-AXS, 2001) was used for absorption correction. 
wR2(int) was 0.0559 before and 0.0522 after correction. 
The Ratio of minimum to maximum transmission is 0.9211. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       twig
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         6394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.066
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0487
_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^)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                5522
_reflns_number_total             6394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401514s_si_003.cif
_cod_data_source_block           gms02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1547480