An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin
Ana L. Silva; Rubén A. Toscano; Luis A. Maldonado; Journal of Organic Chemistry 78 (2013) 5282–5292; doi:10.1021/jo400399q

data_4028272
_publ_section_title
;
 An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5282
_journal_page_last               5292
_journal_paper_doi               10.1021/jo400399q
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
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_symmetry_space_group_name_Hall  'P 2yb'
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_cell_angle_alpha                90
_cell_angle_beta                 93.713(2)
_cell_angle_gamma                90
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_cell_length_a                   7.1704(2)
_cell_length_b                   9.1427(2)
_cell_length_c                   9.7023(2)
_cell_measurement_reflns_used    7714
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      73.4793
_cell_measurement_theta_min      4.5632
_cell_volume                     634.72(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
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_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.632
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_diffrn_standards_decay_%        0
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_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.205
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.185
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_refine_ls_abs_structure_details
;
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0516P)^2^+0.0482P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2304
_reflns_number_total             2545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo400399q_si_001.cif
_cod_data_source_block           129MGL12
_cod_database_code               4028272
_shelx_estimated_absorpt_t_min   0.782
_shelx_estimated_absorpt_t_max   0.892
_shelxl_version_number           2012-6
_shelx_res_checksum              34620