Total Synthesis, Configuration Assignment, and Cytotoxic Activity Evaluation of Protulactone A.
Markovič, Martin; Koóš, Peter; Čarný, Tomáš; Sokoliová, Saskia; Boháčiková, Nikola; Moncol, Ján; Gracza, Tibor; Journal of natural products 80 (2017) 1631–1638; doi:10.1021/acs.jnatprod.7b00212

data_1546204
_publ_section_title
;
 Total Synthesis, Configuration Assignment, and Cytotoxic Activity
 Evaluation of Protulactone A.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1631
_journal_page_last               1638
_journal_paper_doi               10.1021/acs.jnatprod.7b00212
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H26 O5 Si'
_chemical_formula_sum            'C14 H26 O5 Si'
_chemical_formula_weight         302.44
_chemical_name_systematic
3,6-Anhydro-2,8-dideoxy-5-O-tert-butyldimethylsilyl-D-glycero-D-gluco-octano-1,4-lactone
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.899(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2011(4)
_cell_length_b                   7.0991(4)
_cell_length_c                   19.4230(13)
_cell_measurement_reflns_used    36326
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.59
_cell_measurement_theta_min      4.56
_cell_volume                     854.94(9)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23458
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.812
_diffrn_reflns_theta_min         2.275
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.349
_exptl_absorpt_correction_T_max  0.723
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   X-AREA
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0641
_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^)+(0.1302P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.492
_reflns_Friedel_fraction_full    0.611
_reflns_Friedel_fraction_max     0.569
_reflns_number_gt                2147
_reflns_number_total             2667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00212_si_002.cif
_cod_data_source_block           ent-13
_cod_database_code               1546204
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.601
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c), C12(H12a,H12b,H12c),
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'