Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolideseco-Acid from the Madagascar Marine Cyanobacterium Lyngbya majuscula
Marcelino Gutiérrez; Eric H. Andrianasolo; Won Kyo Shin; Douglas E. Goeger; Alexandre Yokochi; Jörg Schemies; Manfred Jung; Dennis France; Susan Cornell-Kennon; Eun Lee; William H. Gerwick; Journal of Organic Chemistry 74 (2009) 5267–5275; doi:10.1021/jo900578j

data_4024661
_publ_section_title
;
Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2
Selective Inhibitor, and Tanikolideseco-Acid from the Madagascar Marine
Cyanobacterium Lyngbya majuscula
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5267
_journal_page_last               5275
_journal_paper_doi               10.1021/jo900578j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C17 H34 O4'
_chemical_formula_weight         302.44
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.180(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.524(4)
_cell_length_b                   8.048(5)
_cell_length_c                   20.295(12)
_cell_measurement_reflns_used    2048
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.64
_cell_measurement_theta_min      2.25
_cell_volume                     895.2(10)
_computing_cell_refinement       TwinSolve
_computing_data_collection       TwinSolve
_computing_data_reduction        TwinSolve
_computing_molecular_graphics    'ORTEP-III for windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.855
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'R-AXIS-CS3 6.X, c++'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.1640
_diffrn_reflns_av_sigmaI/netI    0.0061
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8951
_diffrn_reflns_theta_full        71.19
_diffrn_reflns_theta_max         71.19
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  6  and  1
   Laue group:  2/m (b)
   Friedel opposites are not equivalent.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0882
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0982P)^2^+2.2284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.2358
_reflns_number_gt                2089
_reflns_number_total             2294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900578j_si_001.cif
_cod_data_source_block           xl
_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_H-M      P21
_cod_database_code               4024661