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_7155380
_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
(3R,4R,5R)-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   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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3617(3)
_cell_length_b                   10.0016(3)
_cell_length_c                   20.4847(7)
_cell_measurement_reflns_used    6452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6950
_cell_measurement_theta_min      4.2740
_cell_volume                     1303.38(9)
_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    'SIR2004 (Burla et al., 2007)'
_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 0.996
_diffrn_measurement_details
;
  1 omega -122.00   20.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -19.0000  -90.0000 355

  2 omega -129.00  -35.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  178.0000   90.0000 235

  3 omega   57.00  129.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  178.0000   60.0000 180

  4 omega   25.00  115.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524 -111.0000  150.0000 225

  5 omega   28.00   98.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000  120.0000 175

  6 omega   28.00   98.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000  150.0000 175

  7 omega  100.00  178.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000 -150.0000 195

  8 omega   26.00   90.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  -30.0000 160

  9 omega   74.00  178.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -90.0000 260

 10 omega -116.00   -6.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  150.0000 275

 11 omega -122.00   -2.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000   90.0000 300

 12 omega   76.00  178.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  120.0000 255

 13 omega   20.00  108.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000  -60.0000 220

 14 omega   69.00  177.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000 -150.0000 270

 15 omega   69.00  177.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000   60.0000 270

 16 omega -122.00   -2.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000  -90.0000 300

 17 omega  -49.00   41.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000   90.0000 225

 18 omega   74.00  178.00   0.4000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -30.0000 260
;
_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      0.0627214000
_diffrn_orient_matrix_UB_12      -0.1485291000
_diffrn_orient_matrix_UB_13      0.0031666000
_diffrn_orient_matrix_UB_21      0.0899808000
_diffrn_orient_matrix_UB_22      0.0090507000
_diffrn_orient_matrix_UB_23      -0.0697320000
_diffrn_orient_matrix_UB_31      0.2157756000
_diffrn_orient_matrix_UB_32      0.0397197000
_diffrn_orient_matrix_UB_33      0.0280991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            11491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.856
_diffrn_reflns_theta_min         4.317
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.954
_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    1.021
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.7354
_exptl_crystal_size_mid          0.0654
_exptl_crystal_size_min          0.0517
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0732P)^2^+0.2898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2271
_reflns_number_total             2530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01585a2.cif
_cod_data_source_block           str1704
_cod_depositor_comments
'Adding full bibliography for 7155377--7155385.cif.'
_cod_original_cell_volume        1303.39(8)
_cod_database_code               7155380
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C12 H25 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:
 C4(H4), C5(H5), C7(H7), C3(H3)
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:
 C9(H9A,H9B,H9C), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C2(H2A,H2B,H2C),
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_shelx_res_checksum              85159
_olex2_submission_special_instructions 'No special instructions were received'