Two-step, high-yielding total synthesis of antibiotic pyrones.
Hussain, Akram; Sravanthi, Revoju; Katta, Sunitha; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 22 (2024) 554–560; doi:10.1039/d3ob01923c

data_7159719
_publ_section_title
;
 Two-step, high-yielding total synthesis of antibiotic pyrones.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              554
_journal_page_last               560
_journal_paper_doi               10.1039/d3ob01923c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H26 O3'
_chemical_formula_sum            'C16 H26 O3'
_chemical_formula_weight         266.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                81.850(2)
_cell_angle_beta                 88.334(2)
_cell_angle_gamma                87.904(2)
_cell_formula_units_Z            4
_cell_length_a                   9.1560(2)
_cell_length_b                   10.2227(2)
_cell_length_c                   17.7959(4)
_cell_measurement_reflns_used    11092
_cell_measurement_temperature    298.3
_cell_measurement_theta_max      22.7630
_cell_measurement_theta_min      2.1550
_cell_volume                     1647.27(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.3
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -37.00  22.00   0.50    6.00    --  -14.97 -94.00   0.00  118
  2  \w    -37.00  53.00   0.50    6.00    --   16.22 -94.00  90.00  180
  3  \w    -37.00  53.00   0.50    6.00    --   16.22 -94.00 120.00  180
  4  \w    -43.00  20.00   0.50    6.00    --  -14.97 -91.00 173.00  126
  5  \w    -57.00  41.00   0.50    6.00    --   16.22 -30.00 -90.00  196
  6  \w    -37.00  22.00   0.50    6.00    --  -14.97 -94.00-150.00  118
  7  \w    -57.00  41.00   0.50    6.00    --   16.22 -30.00-180.00  196
  8  \w    -54.00  41.00   0.50    6.00    --   16.22 -45.00-180.00  190
  9  \w    -51.00  45.00   0.50    6.00    --  -14.97  91.00 -72.00  192
 10  \w    -19.00  44.00   0.50    6.00    --   16.22  91.00 -72.00  126
 11  \w    -63.00  75.00   0.50    6.00    --   16.22 -15.00 -90.00  276
 12  \w    -69.00 -10.00   0.50    6.00    --  -14.97 125.00-150.00  118
 13  \w    -69.00 -10.00   0.50    6.00    --  -14.97 125.00 -60.00  118
 14  \w    -69.00 -10.00   0.50    6.00    --  -14.97 125.00 -30.00  118
 15  \w    -31.00  -2.00   0.50    6.00    --   16.22 114.00  67.51   58
 16  \w    -39.00  55.00   0.50    6.00    --  -14.97  45.00  90.00  188
 17  \w    -44.00  52.00   0.50    6.00    --   16.22 -91.00 173.00  192
 18  \w    -57.00  41.00   0.50    6.00    --   16.22 -30.00 120.00  196
 19  \w    -88.00  16.00   0.50    6.00    --  -14.97 -77.00  60.00  208
 20  \w    -89.00  10.00   0.50    6.00    --  -14.97 -30.00 150.00  198
 21  \w    -89.00 -26.50   0.50    6.00    --  -14.97 -30.00 -90.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0457366000
_diffrn_orient_matrix_UB_12      0.0455818000
_diffrn_orient_matrix_UB_13      -0.0223840000
_diffrn_orient_matrix_UB_21      0.0064016000
_diffrn_orient_matrix_UB_22      -0.0426618000
_diffrn_orient_matrix_UB_23      -0.0281574000
_diffrn_orient_matrix_UB_31      -0.0622898000
_diffrn_orient_matrix_UB_32      0.0319468000
_diffrn_orient_matrix_UB_33      -0.0181182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.954
_diffrn_reflns_theta_min         2.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0884
_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^)+(0.1528P)^2^+0.3783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2591
_refine_ls_wR_factor_ref         0.3129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3313
_reflns_number_total             6897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01923c4.cif
_cod_data_source_block           dbr67
_cod_depositor_comments
;
Adding full bibliography for 7159717--7159719.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H52 O6'
_cod_original_formula_weight         532.73
_cod_original_formula_moiety         '2(C16 H26 O3)'
_cod_original_formula_units_Z            2
_cod_database_code               7159719
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C13)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C2(H2A,H2B), C1(H1A,H1B), C18(H18A,H18B), C20(H20A,H20B),
 C19(H19A,H19B), C4(H4A,H4B), C3(H3A,H3B), C21(H21A,H21B), C5(H5A,H5B),
 C22(H22A,H22B), C6(H6A,H6B), C23(H23A,H23B), C7(H7A,H7B), C24(H24A,H24B),
 C8(H8A,H8B), C15(H15A,H15B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C11(H11)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C32(H29,H32A,H32B)
3.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_shelx_res_checksum              52979
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.505