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_7155381
_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         'C12 H24 O2'
_chemical_formula_sum            'C12 H24 O2'
_chemical_formula_weight         200.31
_chemical_name_systematic
(3S,4S,5S)-2,4,6,6-tetramethyloct-7-ene-3,5-diol
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-05
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.35866(12)
_cell_length_b                   9.99503(17)
_cell_length_c                   20.4733(3)
_cell_measurement_reflns_used    6950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.0000
_cell_measurement_theta_min      4.2650
_cell_volume                     1301.18(4)
_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)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -122.00   20.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -19.0000 -180.0000 355

  2 omega   57.00  129.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  178.0000    0.0000 180

  3 omega   26.00   90.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000   60.0000 160

  4 omega   26.00   90.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  120.0000 160

  5 omega   28.00  140.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -61.0000  -30.0000 280

  6 omega   25.00  115.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524 -111.0000  -30.0000 225

  7 omega   26.00   90.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  -30.0000 160

  8 omega   20.00  108.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000    0.0000 220

  9 omega -116.00   -6.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000   90.0000 275

 10 omega -116.00   -6.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  -30.0000 275

 11 omega   26.00  178.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000  150.0000 380

 12 omega   26.00  178.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000  -60.0000 380

 13 omega   20.00  108.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000  150.0000 220

 14 omega   71.00  177.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000    0.0000 265

 15 omega  -49.00   41.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000    0.0000 225

 16 omega   57.00  129.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  178.0000 -180.0000 180

 17 omega  100.00  178.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000   30.0000 195

 18 omega   76.00  128.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -30.0000 130
;
_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      0.0201607000
_diffrn_orient_matrix_UB_12      0.1533981000
_diffrn_orient_matrix_UB_13      -0.0038663000
_diffrn_orient_matrix_UB_21      -0.0541116000
_diffrn_orient_matrix_UB_22      0.0106300000
_diffrn_orient_matrix_UB_23      0.0731718000
_diffrn_orient_matrix_UB_31      0.2352880000
_diffrn_orient_matrix_UB_32      -0.0106223000
_diffrn_orient_matrix_UB_33      0.0171308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.955
_diffrn_reflns_theta_min         4.319
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.979
_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_density_diffrn    1.023
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3547
_exptl_crystal_size_mid          0.0972
_exptl_crystal_size_min          0.0753
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0885P)^2^+0.0786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2389
_reflns_number_total             2539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01585a2.cif
_cod_data_source_block           str1705
_cod_depositor_comments
'Adding full bibliography for 7155377--7155385.cif.'
_cod_database_code               7155381
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C12 H24 O2'
_reflns_odcompleteness_completeness 99.93
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4), C7(H7), C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.c X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C6(H6A,H6B,H6C), C1(H1A,H1B,H1C),
 C3(H3A,H3B,H3C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              58121
_olex2_submission_special_instructions 'No special instructions were received'