Antineoplastic agents. 599. Total synthesis of dolastatin 16.
Pettit, George R.; Smith, Thomas H.; Arce, Pablo M.; Flahive, Erik J.; Anderson, Collin R.; Chapuis, Jean-Charles; Xu, Jun-Ping; Groy, Thomas L.; Belcher, Paul E.; Macdonald, Christian B.; Journal of natural products 78 (2015) 476–485; doi:10.1021/np500925y

data_1518732
_publ_section_title
;
 Antineoplastic agents. 599. Total synthesis of dolastatin 16.
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              476
_journal_page_last               485
_journal_paper_doi               10.1021/np500925y
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C47 H70 N6 O10, 1.625(C H2 Cl2)'
_chemical_formula_sum            'C48.63 H73.25 Cl3.25 N6 O10'
_chemical_formula_weight         1017.09
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3987(10)
_cell_length_b                   18.7734(18)
_cell_length_c                   27.849(3)
_cell_measurement_reflns_used    9674
_cell_measurement_temperature    123.(2)
_cell_measurement_theta_max      22.8588
_cell_measurement_theta_min      2.1696
_cell_volume                     5436.7(9)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XShell ver. 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'Bruker APEX2 v1013.6-2 (Bruker-AXS, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            45655
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.82
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2169
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.095
_refine_diff_density_max         1.493
_refine_diff_density_min         -0.509
_refine_ls_abs_structure_details
;
Flack x determined using 3494 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         10048
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0947P)^2^+2.2792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                8727
_reflns_number_total             10048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np500925y_si_001.cif
_cod_data_source_block           Arce_PA_Book2_171
_cod_depositor_comments          'Adding full bibliography for 1518732.cif.'
_cod_database_code               1518732
_shelx_res_checksum              87734
_shelx_hkl_checksum              83968