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_4517755
_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            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_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_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-09
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_audit_update_record
;
2017-02-24 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 102.5485(8)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   9.90829(8)
_cell_length_b                   9.74229(7)
_cell_length_c                   19.67523(17)
_cell_measurement_reflns_used    26099
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7630
_cell_measurement_theta_min      4.6090
_cell_volume                     1853.87(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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 0.9886
_diffrn_measured_fraction_theta_max 0.9980
_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 -60.00   84
  2  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00 -30.00   88
  3  \w     20.00 104.00   1.00    1.00    --   36.95  57.00   0.00   84
  4  \w     24.00  91.00   1.00    1.00    --   36.95-126.00-129.00   67
  5  \w     10.00 105.00   1.00    1.00    --   36.95  77.00  60.00   95
  6  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
  7  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00-120.00   75
  8  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00 -60.00   75
  9  \w    -34.00  66.00   1.00    1.00    --   36.95 -19.00-120.00  100
 10  \w     23.00  90.00   1.00    1.00    --   36.95-125.00-180.00   67
 11  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00  60.00   88
 12  \w      2.00  29.00   1.00    1.00    --   36.95  91.00 100.71   27
 13  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-180.00   84
 14  \w     44.00 131.00   1.00    1.00    --  111.00 -64.00  30.00   87
 15  \w     92.00 178.00   1.00    1.00    --  111.00  38.00   0.00   86
 16  \w     41.00 116.00   1.00    1.00    --  111.00-111.00-150.00   75
 17  \w     94.00 178.00   1.00    1.00    --  111.00  50.00 -90.00   84
 18  \w     44.00 131.00   1.00    1.00    --  111.00 -64.00 150.00   87
 19  \w     92.00 178.00   1.00    1.00    --  111.00  38.00  90.00   86
 20  \w     43.00 128.00   1.00    1.00    --  111.00 -50.00 -90.00   85
 21  \w     41.00 116.00   1.00    1.00    --  111.00-111.00  30.00   75
 22  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00-180.00   88
 23  \w     41.00 157.00   1.00    1.00    --  111.00 -12.00 120.00  116
 24  \w     41.00 116.00   1.00    1.00    --  111.00-111.00  60.00   75
 25  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00  60.00   95
 26  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00  90.00   88
 27  \w     94.00 178.00   1.00    1.00    --  111.00  50.00-120.00   84
 28  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 -90.00   75
 29  \w     94.00 178.00   1.00    1.00    --  111.00  50.00 -30.00   84
 30  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00 -30.00   88
 31  \w     44.00 131.00   1.00    1.00    --  111.00 -64.00 -90.00   87
 32  \w     92.00 178.00   1.00    1.00    --  111.00  38.00 -30.00   86
 33  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 -60.00   75
 34  \w     91.00 178.00   1.00    1.00    --  111.00  64.00  30.00   87
 35  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 120.00   75
 36  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 150.00   75
 37  \w     94.00 178.00   1.00    1.00    --  111.00  50.00 120.00   84
 38  \w    100.00 178.00   1.00    1.00    --  111.00 111.00-120.00   78
 39  \w     84.00 178.00   1.00    1.00    --  111.00  77.00-150.00   94
 40  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 -90.00   95
 41  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 150.00   95
 42  \w     41.00 116.00   1.00    1.00    --  111.00-111.00-180.00   75
 43  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00 -90.00   88
 44  \w     94.00 178.00   1.00    1.00    --  111.00  50.00 150.00   84
 45  \w     42.00 146.00   1.00    1.00    --  111.00 -92.00 -60.00  104
 46  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 -30.00   95
 47  \w     41.00 157.00   1.00    1.00    --  111.00 -12.00 -60.00  116
 48  \w    -56.00  18.00   1.00    1.00    --  -36.95  38.00-120.00   74
;
_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      -0.0670799000
_diffrn_orient_matrix_UB_12      -0.1423575000
_diffrn_orient_matrix_UB_13      0.0012105000
_diffrn_orient_matrix_UB_21      0.0455460000
_diffrn_orient_matrix_UB_22      -0.0028516000
_diffrn_orient_matrix_UB_23      0.0800147000
_diffrn_orient_matrix_UB_31      -0.1370825000
_diffrn_orient_matrix_UB_32      0.0687417000
_diffrn_orient_matrix_UB_33      0.0057661000
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37890
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.8902
_diffrn_reflns_theta_min         2.3005
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.583
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.0670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                7251
_reflns_number_total             7371
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {570cea36-6994-4c8b-b621-291524caae51}
_cod_data_source_file            ao0c01331_si_004.cif
_cod_data_source_block           ban17_12sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517755