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_7155378
_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         'C16 H28 O4'
_chemical_formula_sum            'C16 H28 O4'
_chemical_formula_weight         284.38
_chemical_name_systematic
(R)-5-((3R,4R,5R)-3,5-dimethoxy-2,4,6-trimethylheptan-2-yl)furan-2(5H)-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   mixed
_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                 97.8329(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.71157(9)
_cell_length_b                   12.95291(17)
_cell_length_c                   20.1272(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1733.42(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29956
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.986
_diffrn_reflns_theta_min         4.070
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       monocristal
_exptl_crystal_F_000             624
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         6023
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0484
_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^)+(0.1006P)^2^+0.0167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5625
_reflns_number_total             6023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01585a2.cif
_cod_data_source_block           str1659
_cod_depositor_comments
'Adding full bibliography for 7155377--7155385.cif.'
_cod_database_code               7155378
_shelxl_version_number           2013-3
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7(0.061) H11(0.073) H5(0.073) H4(0.077) H12(0.089) H10A(0.107)
 H10B(0.107) H10C(0.107) H9A(0.108) H9B(0.108) H9C(0.108) H13(0.099) H3(0.104)
 H15A(0.152) H15B(0.152) H15C(0.152) H6A(0.148) H6B(0.148) H6C(0.148)
 H16A(0.151) H16B(0.151) H16C(0.151) H1A(0.172) H1B(0.172) H1C(0.172)
 H2A(0.178) H2B(0.178) H2C(0.178) H23(0.082) H27(0.089) H26A(0.117) H26B(0.117)
 H26C(0.117) H20(0.092) H25A(0.14) H25B(0.14) H25C(0.14) H19(0.12) H21(0.096)
 H29(0.118) H28(0.109) H31A(0.142) H31B(0.142) H31C(0.142) H17A(0.182)
 H22A(0.188) H22B(0.188) H22C(0.188) H18A(0.187) H18B(0.187) H18C(0.187)
 H32A(0.218) H32B(0.218) H32C(0.218)
 Fixed X: H7(-0.6753) H11(-0.9532) H5(-0.9051) H4(-0.8138) H12(-1.1603) H10A(-
 1.2028) H10B(-1.2608) H10C(-1.2049) H9A(-0.9439) H9B(-0.9904) H9C(-0.7709)
 H13(-0.9194) H3(-0.7479) H15A(-1.0552) H15B(-1.2766) H15C(-1.1064) H6A(-
 0.5151) H6B(-0.6095) H6C(-0.5582) H16A(-0.6145) H16B(-0.702) H16C(-0.5739)
 H1A(-0.9323) H1B(-0.9997) H1C(-1.1354) H2A(-1.113) H2B(-0.9479) H2C(-0.9042)
 H23(-0.3031) H27(-0.5838) H26A(-0.8272) H26B(-0.8903) H26C(-0.8367) H20(-
 0.4305) H25A(-0.5605) H25B(-0.6342) H25C(-0.4071) H21(-0.5558) H29(-0.5572)
 H28(-0.7933) H31A(-0.7211) H31B(-0.8852) H31C(-0.6592) H17A(-0.5057) H22A(-
 0.1541) H22B(-0.2681) H22C(-0.2097) H18A(-0.6014) H18B(-0.6531) H18C(-0.7864)
 H32A(-0.2532) H32B(-0.2926) H32C(-0.1751)
 Fixed Y: H7(-0.8505) H11(-0.8317) H5(-0.8464) H4(-1.0562) H12(-0.6685) H10A(-
 0.8788) H10B(-0.7629) H10C(-0.8332) H9A(-0.6983) H9B(-0.6331) H9C(-0.6719)
 H13(-0.5533) H3(-1.0221) H15A(-1.1028) H15B(-1.1052) H15C(-1.1646) H6A(-
 0.9312) H6B(-0.8827) H6C(-0.8123) H16A(-0.9659) H16B(-1.0756) H16C(-1.017)
 H1A(-0.8758) H1B(-0.9591) H1C(-0.9354) H2A(-1.1321) H2B(-1.1438) H2C(-1.1814)
 H23(-0.4354) H27(-0.5137) H26A(-0.491) H26B(-0.3878) H26C(-0.3882) H20(-
 0.5612) H25A(-0.2542) H25B(-0.2461) H25C(-0.2682) H21(-0.3617) H29(-0.3246)
 H28(-0.38) H31A(-0.6587) H31B(-0.6578) H31C(-0.6775) H17A(-0.6066) H22A(-
 0.4239) H22B(-0.3366) H22C(-0.3206) H18A(-0.3168) H18B(-0.362) H18C(-0.3906)
 H32A(-0.6211) H32B(-0.6804) H32C(-0.5755)
 Fixed Z: H7(-0.3423) H11(-0.4672) H5(-0.2458) H4(-0.2653) H12(-0.4817) H10A(-
 0.398) H10B(-0.3891) H10C(-0.3259) H9A(-0.2828) H9B(-0.3487) H9C(-0.3251) H13(-
 0.5177) H3(-0.151) H15A(-0.3541) H15B(-0.3374) H15C(-0.2916) H6A(-0.237) H6B(-
 0.1771) H6C(-0.2358) H16A(-0.4275) H16B(-0.4156) H16C(-0.3564) H1A(-0.1392)
 H1B(-0.0903) H1C(-0.1583) H2A(-0.1727) H2B(-0.11) H2C(-0.1807) H23(-0.2074)
 H27(-0.3237) H26A(-0.2464) H26B(-0.2841) H26C(-0.2059) H20(-0.0814) H25A(-
 0.2079) H25B(-0.285) H25C(-0.2594) H21(-0.1274) H29(-0.4634) H28(-0.3927)
 H31A(-0.1594) H31B(-0.1109) H31C(-0.0824) H17A(0.0327) H22A(-0.0865) H22B(-
 0.0531) H22C(-0.1252) H18A(-0.0198) H18B(0.0481) H18C(-0.0195) H32A(-0.2524)
 H32B(-0.1876) H32C(-0.1815)
;
_shelx_res_checksum              64411