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_4027643
_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         'C32 H32 Br N5 O7'
_chemical_formula_sum            'C32 H32 Br N5 O7'
_chemical_formula_weight         678.54
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9799(18)
_cell_length_b                   28.093(3)
_cell_length_c                   6.3717(6)
_cell_measurement_reflns_used    4588
_cell_measurement_temperature    200
_cell_measurement_theta_max      49.91
_cell_measurement_theta_min      2.81
_cell_volume                     3397.4(6)
_computing_cell_refinement       'SAINT V7.34A(Bruker AXS, 2007)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.34A(Bruker AXS, 2007)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.099
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            36101
_diffrn_reflns_theta_full        72.20
_diffrn_reflns_theta_max         72.20
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_T_max  0.8465
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
The crystal structure has been squeezed out with PLATON to remove high
disordered ethyl acetate contribution from its solvate structure.
PLATON found a total of 433.8 A^3 solvent accessible void volume with 
contribution from 106 electrons per cell. More precisely, there are two 
voids of 216 A^3 with 53 electrons contribution estimated to contain ethyl 
acetate used as crystallization solvent.
Considering the solvent the physical data should be:
Formula moiety: 'C32 H32 Br N5 O7, 0,5(C4 H8 O2)' or 'C34 H36 Br N5 O8'
Density: 1.413 g cm-3
Absorption coefficient: 2.14 mm-1
F000: 1496.0
;
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), 2796 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.00049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6632
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                4263
_reflns_number_total             6632
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo301638z_si_010.cif
_cod_data_source_block           benit7
_cod_database_code               4027643