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_7159718
_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_absolute_configuration syn
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2023-12-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-12-13 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                96.982(7)
_cell_angle_beta                 91.685(8)
_cell_angle_gamma                96.327(9)
_cell_formula_units_Z            2
_cell_length_a                   5.2134(6)
_cell_length_b                   9.7698(10)
_cell_length_c                   15.9903(12)
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    297.6
_cell_measurement_theta_max      24.5630
_cell_measurement_theta_min      2.1050
_cell_volume                     802.73(14)
_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      297.6
_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 1.000
_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    -41.00  59.00   0.50   14.95    --  -14.97  30.00 -30.00  200
  2  \w    -11.00  86.00   0.50   14.95    --   16.22  61.00-120.00  194
  3  \w    -41.00  59.00   0.50   14.95    --  -14.97  30.00-180.00  200
  4  \w    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 -90.00  118
  5  \w     26.00  90.00   0.50   14.95    --   16.22-155.00 -90.00  128
  6  \w     10.00  71.00   0.50   14.95    --   16.22-125.00  30.00  122
  7  \w      7.00  68.00   0.50   14.95    --   16.22-120.00  66.00  122
  8  \w    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 120.00  118
  9  \w    -37.00  22.00   0.50   14.95    --  -14.97 -94.00  90.00  118
 10  \w    -54.00  41.00   0.50   14.95    --   16.22 -45.00  30.00  190
 11  \w    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 -60.00  118
 12  \w    -57.00  41.00   0.50   14.95    --   16.22 -30.00 -90.00  196
 13  \w    -39.00  55.00   0.50   14.95    --  -14.97  45.00 -90.00  188
 14  \w    -39.00  55.00   0.50   14.95    --  -14.97  45.00-180.00  188
 15  \w    -41.00  59.00   0.50   14.95    --  -14.97  30.00-180.00  200
 16  \w    -57.00  41.00   0.50   14.95    --   16.22 -30.00-180.00  196
 17  \w    -88.00 -26.00   0.50   14.95    --  -14.97 155.00 -51.00  124
 18  \w    -63.00  75.00   0.50   14.95    --   16.22 -15.00   0.00  276
 19  \w    -65.00  -6.00   0.50   14.95    --  -14.97 120.00 151.00  118
 20  \w    -89.00  10.00   0.50   14.95    --  -14.97 -30.00   0.00  198
 21  \w    -85.00  13.00   0.50   14.95    --  -14.97 -61.00 -60.00  196
;
_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      -0.1010969000
_diffrn_orient_matrix_UB_12      -0.0445642000
_diffrn_orient_matrix_UB_13      0.0145882000
_diffrn_orient_matrix_UB_21      -0.0258992000
_diffrn_orient_matrix_UB_22      -0.0341092000
_diffrn_orient_matrix_UB_23      -0.0416219000
_diffrn_orient_matrix_UB_31      0.0887807000
_diffrn_orient_matrix_UB_32      -0.0476648000
_diffrn_orient_matrix_UB_33      0.0074651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_unetI/netI     0.2048
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15181
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47829
_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 whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.044
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.2517
_refine_ls_R_factor_gt           0.0827
_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^)+(0.0781P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.2148
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                1322
_reflns_number_total             4392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01923c4.cif
_cod_data_source_block           dbr70
_cod_depositor_comments
'Adding full bibliography for 7159717--7159719.cif.'
_cod_database_code               7159718
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.42
_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(C21) = Uanis(C20) = Uanis(C19)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C28(H28)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C27(H27A,H27B), C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B),
 C17(H17A,H17B), C4(H4A,H4B), C18(H18A,H18B), C1(H1A,H1B), C19(H19A,H19B),
 C5(H5A,H5B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C10(H10)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C6(H6A,H6B,H6C), C21(H21A,H21B,H21C)
3.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2)
;
_shelx_res_checksum              22208
_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 2.113
_oxdiff_exptl_absorpt_empirical_full_min 0.468