Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring.
Roldán, Steven; Cardona, Adrià; Conesa, Laura; Murga, Juan; Falomir, Eva; Carda, Miguel; Marco, J. Alberto; Organic & biomolecular chemistry 15 (2016) 220–232; doi:10.1039/c6ob01585a

data_7155383
_publ_section_title
;
 Synthesis and biological evaluation of simplified pironetin analogues
 with modifications in the side chain and the lactone ring.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              220
_journal_page_last               232
_journal_paper_doi               10.1039/c6ob01585a
_journal_volume                  15
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H54 O4 Si2'
_chemical_formula_sum            'C27 H54 O4 Si2'
_chemical_formula_weight         498.88
_chemical_name_systematic
(R)-6-((3S,4S,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2,4,6-trimethylheptan-2-yl)-5,6-dihydro-2H-pyran-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-15 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3349(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.67692(13)
_cell_length_b                   7.47473(8)
_cell_length_c                   15.84227(18)
_cell_measurement_temperature    293(2)
_cell_volume                     1575.91(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27047
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.975
_diffrn_reflns_theta_min         3.321
_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_description       fiber
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.5922
_exptl_crystal_size_mid          0.1462
_exptl_crystal_size_min          0.1004
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.010(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0492
_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^)+(0.1051P)^2^+0.1454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                5305
_reflns_number_total             5445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01585a2.cif
_cod_data_source_block           str1726
_cod_depositor_comments
'Adding full bibliography for 7155377--7155385.cif.'
_cod_database_code               7155383
_shelxl_version_number           2013-3
_shelx_res_checksum              59622