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_4028645
_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         'C9 H9 Br O4'
_chemical_formula_sum            'C9 H9 Br O4'
_chemical_formula_weight         261.07
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-04-11
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-04-17 - Report on C9 H9 Br O4 
             by Anthony C. Willis
             for Aymeric Cervi and Martin Banwell

2013-04-17 - passes checkcif tests with a few warnings  
;
_cell_angle_alpha                69.3110(12)
_cell_angle_beta                 79.7077(14)
_cell_angle_gamma                70.2086(12)
_cell_formula_units_Z            4
_cell_length_a                   8.2473(2)
_cell_length_b                   10.0370(2)
_cell_length_c                   13.0591(2)
_cell_measurement_reflns_used    20758
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     949.42(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.050
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26967
_diffrn_reflns_theta_full        30.052
_diffrn_reflns_theta_max         30.052
_diffrn_reflns_theta_min         2.631
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.314
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_correction_T_min  0.278
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.49
_refine_ls_extinction_coef       75(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0162
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.0242484
_refine_ls_shift/su_mean         0.0008519
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.59P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0760
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0760
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -12
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4819
_reflns_number_total             5538
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.71
_oxford_diffrn_Wilson_scale      0.74
_oxford_refine_ls_r_factor_ref   0.0368
_oxford_refine_ls_scale          1.632(8)
_oxford_reflns_number_all        5538
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1325 At 15:20 on 11/4/13'
_cod_data_source_file            jo401583q_si_002.cif
_cod_data_source_block           ban1325
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028645
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT BR   (    1 ,X'S,U'S)  UNTIL C    (   19 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  191 ) 
CONT EXTPARAM 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;