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_1507853
_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         'C22 H27 I1 O4'
_chemical_formula_sum            'C22 H27 I O4'
_chemical_formula_weight         482.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-08-06
_audit_creation_method           CRYSTALS_ver_14.06
_cell_angle_alpha                115.738(6)
_cell_angle_beta                 100.251(8)
_cell_angle_gamma                90.978(8)
_cell_formula_units_Z            2
_cell_length_a                   9.376(6)
_cell_length_b                   10.638(3)
_cell_length_c                   12.234(3)
_cell_measurement_reflns_used    8070
_cell_measurement_temperature    293
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     1075.5(8)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21109
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         30.129
_diffrn_reflns_theta_min         1.888
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
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_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.0004760
_refine_ls_shift/su_mean         0.0000180
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 1.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1360
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1360
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              17
_reflns_limit_l_min              0
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_reflns_number_total             6213
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.37
_oxford_diffrn_Wilson_scale      29.41
_oxford_refine_ls_r_factor_ref   0.0672
_oxford_refine_ls_scale          0.20820(15)
_oxford_reflns_number_all        6213
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'mo_10083_0ma in P-1'
_cod_data_source_file            ol3013167_si_001.cif
_cod_data_source_block           10083
_cod_depositor_comments
'Adding full bibliography for 1507853--1507855.cif.'
_cod_original_cell_volume        1075.5(7)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C22 H27 I1 O4'
_cod_database_code               1507853