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_1555401
_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 H23 N O2'
_chemical_formula_weight         297.38
_chemical_name_common            MW5-085
_chemical_name_systematic        sarpong114
_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                 90.259(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5354(6)
_cell_length_b                   8.5029(8)
_cell_length_c                   11.9989(11)
_cell_measurement_reflns_used    3440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.68
_cell_volume                     768.79(12)
_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 0.993
_diffrn_measured_fraction_theta_max 0.983
_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  0.0769
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_refln_scan_rate          20
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.816
_diffrn_reflns_theta_min         3.684
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 891 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0843P)^2^+0.1771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                2346
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02797_si_004.cif
_cod_data_source_block           sarpong114
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555401
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              56197
_shelx_hkl_checksum              81601