Highly Convergent Three Component Benzyne Coupling: The Total Synthesis of ent-Clavilactone B
Igor Larrosa; Marianne I. Da Silva; Patricio M. Gómez; Peter Hannen; Eunjung Ko; Steven R. Lenger; Simon R. Linke; Andrew J. P. White; Donna Wilton; Anthony G. M. Barrett; Journal of the American Chemical Society 128 (2006) 14042–14043; doi:10.1021/ja0662671

data_4111046
_publ_section_title
;
 Highly Convergent Three Component Benzyne Coupling: The Total Synthesis
 of ent-Clavilactone B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14042
_journal_page_last               14043
_journal_paper_doi               10.1021/ja0662671
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C27 H31 N O8'
_chemical_formula_weight         497.53
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.079(14)
_cell_angle_beta                 116.397(17)
_cell_angle_gamma                101.338(15)
_cell_formula_units_Z            2
_cell_length_a                   10.976(2)
_cell_length_b                   11.368(2)
_cell_length_c                   11.4464(18)
_cell_measurement_reflns_used    11742
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.9606
_cell_measurement_theta_min      3.7734
_cell_volume                     1247.9(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9863
_diffrn_measured_fraction_theta_full 0.900
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21990
_diffrn_reflns_theta_full        32.09
_diffrn_reflns_theta_max         32.09
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.03176
_exptl_absorpt_correction_T_min  0.95838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.29.8 (release 17-03-2006 CrysAlis171 .NET) 
(compiled Mar 17 2006,10:57:34) 
empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       shards
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         7850
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0632P)^2^+0.1077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                5981
_reflns_number_total             7850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0662671si20060829_072753_2.cif
_cod_data_source_block           Compound_22
_cod_original_cell_volume        1248.0(4)
_cod_database_code               4111046