Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
Stephen Hanessian; Ramkrishna Reddy Vakiti; Stéphane Dorich; Shyamapada Banerjee; Benoît Deschênes-Simard; Journal of Organic Chemistry 77 (2012) 9458–9472; doi:10.1021/jo301638z

data_4027637
_publ_section_title
;
 Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9458
_journal_page_last               9472
_journal_paper_doi               10.1021/jo301638z
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C40 H42 Br N O7 Si'
_chemical_formula_sum            'C40 H42 Br N O7 Si'
_chemical_formula_weight         756.75
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   26.146(2)
_cell_length_b                   26.146(2)
_cell_length_c                   9.7191(8)
_cell_measurement_reflns_used    25723
_cell_measurement_temperature    150
_cell_measurement_theta_max      53.46
_cell_measurement_theta_min      3.38
_cell_volume                     5754.0(8)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.104
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            78980
_diffrn_reflns_theta_full        57.13
_diffrn_reflns_theta_max         57.13
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             2364
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_platon_squeeze_details
;
The crystal structure has been squeezed out with PLATON to remove high
disordered solvent contribution from its solvate structure.
PLATON found a total of 203 A^3 solvent accessible void volume with 
contribution from 73 electrons per cell. The accessible void may contain either
a molecule of ethyl acetate or hexane used as crystallization solvent.
;
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), 2299 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     802
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.1036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1434P)^2^+11.5630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2734
_refine_ls_wR_factor_ref         0.2959
_reflns_number_gt                2775
_reflns_number_total             5086
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo301638z_si_004.cif
_cod_data_source_block           bent98
_cod_original_cell_volume        5754.1(8)
_cod_database_code               4027637