Total Synthesis and Evaluation of a Key Series of C5-Substituted Vinblastine Derivatives
Porino Va; Erica L. Campbell; William M. Robertson; Dale L. Boger; Journal of the American Chemical Society 132 (2010) 8489–8495; doi:10.1021/ja1027748

data_4102566
_publ_section_title
;
 Total Synthesis and Evaluation of a Key Series of C5-Substituted
 Vinblastine Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8489
_journal_page_last               8495
_journal_paper_doi               10.1021/ja1027748
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C24 H30 N2 O4 S'
_chemical_formula_weight         442.56
_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                   10.547(2)
_cell_length_b                   12.693(3)
_cell_length_c                   17.130(3)
_cell_measurement_temperature    296(2)
_cell_volume                     2293.2(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17022
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9628
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.5400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3547
_reflns_number_total             4049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1027748_si_004.cif
_cod_data_source_block           posu
_cod_original_cell_volume        2293.1(8)
_cod_database_code               4102566