Stereocontrolled Syntheses of (-)-Cubebol and (-)-10-Epicubebol Involving Intramolecular Cyclopropanation of α-Lithiated Epoxides
David M. Hodgson; Saifullah Salik; David J. Fox; Journal of Organic Chemistry 75 (2010) 2157–2168; doi:10.1021/jo9022974

data_4025351
_publ_section_title
;
 Stereocontrolled Syntheses of (-)-Cubebol and (-)-10-Epicubebol Involving
 Intramolecular Cyclopropanation of \a-Lithiated Epoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2157
_journal_page_last               2168
_journal_paper_doi               10.1021/jo9022974
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H26 O1'
_chemical_formula_sum            'C15 H26 O'
_chemical_formula_weight         222.37
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-03
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 91.1046(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8823(2)
_cell_length_b                   9.5332(2)
_cell_length_c                   30.4082(8)
_cell_measurement_reflns_used    4294
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2864.22(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16603
_diffrn_reflns_theta_full        25.283
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         5.096
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.031
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         5958
_refine_ls_number_restraints     629
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.000108
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 4.48P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1513
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1513
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              -12
_reflns_limit_l_max              39
_reflns_limit_l_min              0
_reflns_number_gt                4880
_reflns_number_total             6563
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.81
_oxford_diffrn_Wilson_scale      13.20
_oxford_refine_ls_r_factor_ref   0.0814
_oxford_refine_ls_scale          0.4515(8)
_oxford_reflns_number_all        5958
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6072
_cod_data_source_file            jo9022974_si_002.cif
_cod_data_source_block           6072
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C15 H26 O1'
_cod_database_code               4025351