Construction of Enantiopure Taxoid and Natural Product-like Scaffolds Using a C-C Bond Cleavage/Arylation Reaction.
Weber, Manuel; Owens, Kyle; Masarwa, Ahmad; Sarpong, Richmond; Organic letters 17 (2015) 5432–5435; doi:10.1021/acs.orglett.5b02797

data_1555398
_publ_section_title
;
 Construction of Enantiopure Taxoid and Natural Product-like Scaffolds
 Using a C-C Bond Cleavage/Arylation Reaction.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5432
_journal_page_last               5435
_journal_paper_doi               10.1021/acs.orglett.5b02797
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.40
_chemical_name_common            MW5-023
_chemical_name_systematic        sarpong110
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.193(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2207(6)
_cell_length_b                   10.6225(8)
_cell_length_c                   10.6751(8)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.35
_cell_measurement_theta_min      4.16
_cell_volume                     803.23(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_refln_scan_rate          1
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14841
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.438
_diffrn_reflns_theta_min         4.222
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
; 
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0668
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2831
_reflns_number_total             2878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02797_si_002.cif
_cod_data_source_block           sarpong110
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555398
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              72668
_shelx_hkl_checksum              77319