Synthesis of Structurally Simplified Analogues of Pancratistatin: Truncation of the Cyclitol Ring
Madhuri Manpadi; Artem S. Kireev; Igor V. Magedov; Jeff Altig; Paul Tongwa; Mikhail Yu. Antipin; Antonio Evidente; Willem A. L. van Otterlo; Alexander Kornienko; Journal of Organic Chemistry 74 (2009) 7122–7131; doi:10.1021/jo901494r

data_4024865
_publ_section_title
;
Synthesis of Structurally Simplified Analogues of Pancratistatin:
Truncation of the Cyclitol Ring
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7122
_journal_page_last               7131
_journal_paper_doi               10.1021/jo901494r
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N O9'
_chemical_formula_sum            'C20 H23 N O9'
_chemical_formula_weight         421.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.6880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0278(2)
_cell_length_b                   7.7271(2)
_cell_length_c                   12.6670(2)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      67.3126
_cell_measurement_theta_min      3.4930
_cell_volume                     980.43(4)
_computing_cell_refinement       'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8357
_diffrn_reflns_theta_full        68.92
_diffrn_reflns_theta_max         68.92
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'APEX2  (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0633P)^2^+0.0593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2780
_reflns_number_total             3188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901494r_si_002.cif
_cod_data_source_block           paul17a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024865