Total Syntheses of the Coumarin-Containing Natural Products Pimpinellin and Fraxetin Using Au(I)-Catalyzed Intramolecular Hydroarylation (IMHA) Chemistry
Aymeric Cervi; Paul Aillard; Nourallah Hazeri; Laurent Petit; Christina L. L. Chai; Anthony C. Willis; Martin G. Banwell; Journal of Organic Chemistry 78 (2013) 9876–9882; doi:10.1021/jo401583q

data_4028646
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       'mgb@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        'Martin G. Banwell'
_publ_contact_author_phone       ' 61 2 6125 8202 '
_publ_section_title
;
 Total Syntheses of the Coumarin-Containing Natural Products Pimpinellin
 and Fraxetin Using Au(I)-Catalyzed Intramolecular Hydroarylation (IMHA)
 Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9876
_journal_page_last               9882
_journal_paper_doi               10.1021/jo401583q
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        local
_chemical_formula_moiety         'C20 H30 O4 Si'
_chemical_formula_sum            'C20 H30 O4 Si'
_chemical_formula_weight         362.54
_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             12-02-03
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-02-03 - Report on C20 H30 O4 Si 
             by Anthony C. Willis
             for  Aymeric Cervi and Martin Banwell

2012-02-03 - passes checkcif tests with a few warnings  
;
_cell_angle_alpha                112.714(4)
_cell_angle_beta                 95.776(5)
_cell_angle_gamma                104.045(4)
_cell_formula_units_Z            4
_cell_length_a                   8.5088(7)
_cell_length_b                   15.6234(15)
_cell_length_c                   18.1523(13)
_cell_measurement_reflns_used    20280
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     2107.9(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;  
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) 
;
_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      200
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29429
_diffrn_reflns_theta_full        25.103
_diffrn_reflns_theta_max         25.103
_diffrn_reflns_theta_min         2.688
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.96
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9392
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.0876
_refine_ls_shift/su_max          0.0035121
_refine_ls_shift/su_mean         0.0006995
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 2.46P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2514
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2514
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -18
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3281
_reflns_number_total             7464
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      32.07
_oxford_refine_ls_r_factor_ref   0.1945
_oxford_refine_ls_scale          0.2162(3)
_oxford_reflns_number_all        7464
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '2031002 ban1152'
_cod_data_source_file            jo401583q_si_003.cif
_cod_data_source_block           ban1152
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028646
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (   1,X'S) H   ( 501,X'S) 
RIDE O   (   5,X'S) H   ( 505,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) H   ( 333,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) H   ( 373,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) H   ( 393,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) H   ( 403,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
END                                                                             
;