A reductive-Heck approach to the hydroazulene ring system: a formal synthesis of the englerins.
Gao, Peng; Cook, Silas P.; Organic letters 14 (2012) 3340–3343; doi:10.1021/ol3013167

data_1507854
_publ_section_title
;
 A reductive-Heck approach to the hydroazulene ring system: a formal
 synthesis of the englerins.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3340
_journal_page_last               3343
_journal_paper_doi               10.1021/ol3013167
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H20 O'
_chemical_formula_sum            'C12 H20 O'
_chemical_formula_weight         180.28
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   22.319(4)
_cell_length_b                   22.319(4)
_cell_length_c                   8.5732(13)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.88
_cell_measurement_theta_min      2.55
_cell_volume                     4270.6(13)
_computing_cell_refinement       'APEX II v2010.11.3 (Bruker, 2010)'
_computing_data_collection       'APEX II v2010.11.3 (Bruker, 2010)'
_computing_data_reduction        'APEX II v2010.11.3 (Bruker, 2010)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2010)'
_computing_publication_material  'SHELXTL (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2010)'
_computing_structure_solution    'SIR-2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
'0.30 degree frames measured for 60 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18598
_diffrn_reflns_theta_full        25.70
_diffrn_reflns_theta_max         25.70
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0484P)^2^+4.1059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1649
_reflns_number_total             2034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3013167_si_002.cif
_cod_data_source_block           11007
_cod_depositor_comments
'Adding full bibliography for 1507853--1507855.cif.'
_cod_original_cell_volume        4270.6(11)
_cod_original_sg_symbol_H-M      I4(1)/a
_cod_database_code               1507854