Levoglucosenone and Its Pseudoenantiomer <i>iso</i>-Levoglucosenone as Scaffolds for Drug Discovery and Development.
Liu, Xin; Carr, Paul; Gardiner, Michael G.; Banwell, Martin G.; Elbanna, Ahmed H.; Khalil, Zeinab G.; Capon, Robert J.; ACS omega 5 (2020) 13926–13939; doi:10.1021/acsomega.0c01331

data_4517747
_publ_section_title
;
 Levoglucosenone and Its Pseudoenantiomer <i>iso</i>-Levoglucosenone as
 Scaffolds for Drug Discovery and Development.
;
_journal_issue                   23
_journal_name_full               'ACS omega'
_journal_page_first              13926
_journal_page_last               13939
_journal_paper_doi               10.1021/acsomega.0c01331
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_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_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-17
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_audit_update_record
;
2017-02-27 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.26094(4)
_cell_length_b                   9.56903(5)
_cell_length_c                   13.38456(6)
_cell_measurement_reflns_used    19989
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6650
_cell_measurement_theta_min      3.2090
_cell_volume                     1186.116(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics
'SHELXLE (C. B. H&#x00C3;&#x00BC;bschle et al.,2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_measured_fraction_theta_max 0.9992
_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   -104.00 -20.00   1.00    1.00    --  -36.95 -57.00-120.00   84
  2  \w     18.00 106.00   1.00    1.00    --   36.95  38.00-150.00   88
  3  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00  30.00   88
  4  \w     23.00  90.00   1.00    1.00    --   36.95-125.00 120.00   67
  5  \w    -34.00  66.00   1.00    1.00    --   36.95 -19.00  90.00  100
  6  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00 -90.00   75
  7  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00 150.00   75
  8  \w     20.00 104.00   1.00    1.00    --   36.95  57.00   0.00   84
  9  \w     23.00  90.00   1.00    1.00    --   36.95-125.00 -90.00   67
 10  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00   0.00   88
 11  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00 -30.00   75
 12  \w     41.00 116.00   1.00    2.00    --  111.00-111.00-150.00   75
 13  \w     43.00 138.00   1.00    2.00    --  111.00 -77.00 120.00   95
 14  \w     91.00 178.00   1.00    2.00    --  111.00  64.00 -30.00   87
 15  \w     41.00 136.00   1.00    2.00    --  111.00 -25.00   0.00   95
 16  \w     42.00 146.00   1.00    2.00    --  111.00 -92.00  30.00  104
 17  \w     92.00 178.00   1.00    2.00    --  111.00  38.00 150.00   86
 18  \w    100.00 178.00   1.00    2.00    --  111.00 111.00  90.00   78
 19  \w     42.00 130.00   1.00    2.00    --  111.00 -38.00 150.00   88
 20  \w     57.00 150.00   1.00    2.00    --  111.00 178.00  30.00   93
 21  \w     43.00 128.00   1.00    2.00    --  111.00 -50.00-120.00   85
 22  \w     41.00 116.00   1.00    2.00    --  111.00-111.00   0.00   75
 23  \w     44.00 131.00   1.00    2.00    --  111.00 -64.00 -60.00   87
 24  \w     44.00 131.00   1.00    2.00    --  111.00 -64.00  30.00   87
 25  \w     42.00 130.00   1.00    2.00    --  111.00 -38.00 -30.00   88
 26  \w     43.00 128.00   1.00    2.00    --  111.00 -50.00 -30.00   85
 27  \w     43.00 138.00   1.00    2.00    --  111.00 -77.00 -60.00   95
 28  \w     42.00 146.00   1.00    2.00    --  111.00 -92.00 150.00  104
 29  \w     65.00 178.00   1.00    2.00    --  111.00  12.00 -90.00  113
 30  \w     84.00 178.00   1.00    2.00    --  111.00  77.00-150.00   94
 31  \w     86.00 178.00   1.00    2.00    --  111.00  25.00 -30.00   92
 32  \w     94.00 178.00   1.00    2.00    --  111.00  50.00 120.00   84
 33  \w     41.00 116.00   1.00    2.00    --  111.00-111.00 -60.00   75
 34  \w     44.00 131.00   1.00    2.00    --  111.00 -64.00-120.00   87
 35  \w     41.00 116.00   1.00    2.00    --  111.00-111.00  30.00   75
 36  \w     41.00 116.00   1.00    2.00    --  111.00-111.00  60.00   75
 37  \w    100.00 178.00   1.00    2.00    --  111.00 111.00 -60.00   78
 38  \w    100.00 178.00   1.00    2.00    --  111.00 111.00   0.00   78
 39  \w    100.00 178.00   1.00    2.00    --  111.00 111.00 150.00   78
 40  \w     43.00 128.00   1.00    2.00    --  111.00 -50.00-180.00   85
 41  \w     43.00 128.00   1.00    2.00    --  111.00 -50.00 -90.00   85
 42  \w     92.00 178.00   1.00    2.00    --  111.00  38.00-180.00   86
 43  \w     43.00 128.00   1.00    2.00    --  111.00 -54.00 118.23   85
 44  \w      4.00  33.00   1.00    1.00    --   36.95  89.00 144.60   29
 45  \w      3.00  32.00   1.00    1.00    --   36.95  90.00 -79.06   29
 46  \w    -32.00 106.00   1.00    1.00    --   36.95   0.00-180.00  138
 47  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
 48  \w     10.00 105.00   1.00    1.00    --   36.95  77.00  30.00   95
 49  \w     20.00 104.00   1.00    1.00    --   36.95  57.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358144000
_diffrn_orient_matrix_UB_12      0.0068485000
_diffrn_orient_matrix_UB_13      0.1123435000
_diffrn_orient_matrix_UB_21      0.0156101000
_diffrn_orient_matrix_UB_22      -0.1598935000
_diffrn_orient_matrix_UB_23      0.0073277000
_diffrn_orient_matrix_UB_31      0.1616887000
_diffrn_orient_matrix_UB_32      0.0169536000
_diffrn_orient_matrix_UB_33      0.0241732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24123
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.8344
_diffrn_reflns_theta_min         3.3019
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                2393
_reflns_number_total             2405
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {7b9376af-dd7c-4286-9686-ff0beff9568d}
_cod_data_source_file            ao0c01331_si_011.cif
_cod_data_source_block           ban17_15sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517747