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_7159717
_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         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-27
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5552(4)
_cell_length_b                   7.1623(3)
_cell_length_c                   23.1013(8)
_cell_measurement_reflns_used    6335
_cell_measurement_temperature    298.98
_cell_measurement_theta_max      22.8100
_cell_measurement_theta_min      2.3090
_cell_volume                     2242.82(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      298.98
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -10.00  90.00   0.50    3.00    --   16.22  30.00  30.00  200
  2  \w      1.00  63.00   0.50    3.00    --   16.22-113.00 138.00  124
  3  \w     10.00  71.00   0.50    3.00    --   16.22-125.00  90.00  122
  4  \w    -37.00  21.00   0.50    3.00    --  -15.60 -94.00   0.00  116
  5  \w    -37.00  53.00   0.50    3.00    --   16.22 -94.00   0.00  180
  6  \w    -41.00  58.00   0.50    3.00    --  -15.60  30.00 -90.00  198
  7  \w     -8.00  86.00   0.50    3.00    --   16.22  45.00-120.00  188
  8  \w    -37.00  21.00   0.50    3.00    --  -15.60 -94.00-180.00  116
  9  \w    -37.00  21.00   0.50    3.00    --  -15.60 -94.00 -90.00  116
 10  \w    -40.00  55.00   0.50    3.00    --  -15.60  45.00-180.00  190
 11  \w    -63.00  -1.00   0.50    3.00    --  -15.60 113.00-130.00  124
 12  \w    -11.00  86.00   0.50    3.00    --   16.22  61.00  60.00  194
 13  \w    -40.00  55.00   0.50    3.00    --  -15.60  45.00  90.00  190
 14  \w    -37.00  21.00   0.50    3.00    --  -15.60 -94.00  90.00  116
 15  \w    -57.00  41.00   0.50    3.00    --   16.22 -30.00  60.00  196
 16  \w    -70.00 -10.00   0.50    3.00    --  -15.60 125.00 150.00  120
 17  \w    -87.00  50.50   0.50    3.00    --  -15.60  15.00  60.00  275
;
_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      -0.0016301000
_diffrn_orient_matrix_UB_12      -0.0227761000
_diffrn_orient_matrix_UB_13      0.0298694000
_diffrn_orient_matrix_UB_21      0.0513991000
_diffrn_orient_matrix_UB_22      0.0172216000
_diffrn_orient_matrix_UB_23      0.0022232000
_diffrn_orient_matrix_UB_31      -0.0097132000
_diffrn_orient_matrix_UB_32      0.0948055000
_diffrn_orient_matrix_UB_33      0.0067619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.317
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55306
_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    1.162
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0499P)^2^+2.6121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.2085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                932
_reflns_number_total             1989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01923c4.cif
_cod_data_source_block           dbr71
_cod_depositor_comments
'Adding full bibliography for 7159717--7159719.cif.'
_cod_database_code               7159717
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.988
_reflns_odcompleteness_completeness 99.85
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              93158
_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.605