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_7155377
_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         'C17 H30 O4'
_chemical_formula_sum            'C17 H30 O4'
_chemical_formula_weight         298.41
_chemical_name_systematic
(R)-6-((3R,4R,5R)-3,5-dimethoxy-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_date             2015-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-10-15 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1494(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.89706(6)
_cell_length_b                   13.34116(17)
_cell_length_c                   9.57590(11)
_cell_measurement_reflns_used    10493
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9270
_cell_measurement_theta_min      4.5800
_cell_volume                     878.815(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -129.00  -34.50   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  178.0000   60.0000 135

  2 omega -117.00   -6.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -38.0000   60.0000 158

  3 omega -116.00   -5.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000    0.0000 158

  4 omega   57.00  128.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000   60.0000 102

  5 omega  -46.00   73.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  -77.0000  -90.0000 171

  6 omega   71.00  176.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000   60.0000 151

  7 omega   71.00  176.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000   30.0000 151

  8 omega   71.00  176.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000    0.0000 151

  9 omega   76.00  177.50   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000   30.0000 145

 10 omega   71.00  176.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -30.0000 151

 11 omega   20.00  108.20   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000   60.0000 126

 12 omega   28.00   98.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000   30.0000 100

 13 omega   74.00  176.90   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000   60.0000 147

 14 omega   74.00  176.90   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000    0.0000 147

 15 omega  100.00  177.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000    0.0000 110

 16 omega   74.00  176.90   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000   90.0000 147

 17 omega  100.00  177.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000  150.0000 110

 18 omega   76.00  177.50   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000   60.0000 145

 19 omega   74.00  176.90   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -30.0000 147

 20 omega  100.00  177.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000  -90.0000 110

 21 omega   71.00  176.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   67.0000   21.9399 151

 22 omega   27.00   90.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -35.0000  132.0000 91

 23 omega   76.00  177.50   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000    0.0000 145

 24 omega   76.00  177.50   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000   90.0000 145

 25 omega   74.00  176.90   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000   30.0000 147

 26 omega -116.00   -5.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -150.0000 158

 27 omega  -50.00   41.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   38.0000   60.0000 130

 28 omega -122.00   -2.30   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000  -60.0000 171

 29 omega  -50.00   41.00   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   38.0000  120.0000 130

 30 omega -122.00   -2.30   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000   90.0000 171

 31 omega -116.00   -5.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000  -60.0000 158

 32 omega -116.00   -5.40   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -180.0000 158

 33 omega -122.00   -2.30   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000 -180.0000 171

 34 omega   26.00  138.70   0.7000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000 -120.0000 161
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1534142000
_diffrn_orient_matrix_UB_12      -0.0437050000
_diffrn_orient_matrix_UB_13      0.0923106000
_diffrn_orient_matrix_UB_21      -0.1296464000
_diffrn_orient_matrix_UB_22      -0.0268095000
_diffrn_orient_matrix_UB_23      -0.1326191000
_diffrn_orient_matrix_UB_31      0.0983434000
_diffrn_orient_matrix_UB_32      -0.1033613000
_diffrn_orient_matrix_UB_33      -0.0045751000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14785
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.985
_diffrn_reflns_theta_min         4.630
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  0.682
_exptl_absorpt_correction_T_min  0.461
_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    1.128
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3504
_exptl_crystal_size_mid          0.2982
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0662P)^2^+0.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2947
_reflns_number_total             3014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01585a2.cif
_cod_data_source_block           str1620
_cod_depositor_comments
'Adding full bibliography for 7155377--7155385.cif.'
_cod_original_cell_volume        878.814(17)
_cod_database_code               7155377
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C17 H30 O4'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C7(H7), C5(H5), C4(H4), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C17(H17A,H17B,H17C),
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              96413
_olex2_submission_special_instructions 'No special instructions were received'