SmI2-Mediated Intermolecular Coupling of γ-LactamN-α-Radicals with Activated Alkenes: Asymmetric Synthesis of 11-Hydroxylated Analogues of the Lead Compounds CP-734432 and PF-04475270
Kong-Zhen Hu; Jie Ma; Shi Qiu; Xiao Zheng; Pei-Qiang Huang; Journal of Organic Chemistry 78 (2013) 1790–1801; doi:10.1021/jo301277n

data_4027979
_publ_section_title
;
 SmI2-Mediated Intermolecular Coupling of \g-LactamN-\a-Radicals with
 Activated Alkenes: Asymmetric Synthesis of 11-Hydroxylated Analogues of
 the Lead Compounds CP-734432 and PF-04475270
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1790
_journal_page_last               1801
_journal_paper_doi               10.1021/jo301277n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C23 H22 N2 O4 S'
_chemical_formula_weight         422.49
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4370(13)
_cell_length_b                   9.9383(14)
_cell_length_c                   22.121(3)
_cell_measurement_temperature    273(2)
_cell_volume                     2074.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18416
_diffrn_reflns_theta_full        28.81
_diffrn_reflns_theta_max         28.81
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.189
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             888
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.3124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                4790
_reflns_number_total             5011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301277n_si_002.cif
_cod_data_source_block           a
_cod_original_formula_sum        'C18.40 H17.60 N1.60 O3.20 S0.80'
_cod_database_code               4027979