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_4517753
_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_formula_sum            'C13 H14 Cl2 N2 O2'
_chemical_formula_weight         301.16
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-23
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_audit_update_record
;
2017-08-24 # Formatted by publCIF

;
_cell_angle_alpha                112.584(3)
_cell_angle_beta                 102.063(3)
_cell_angle_gamma                99.352(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3394(3)
_cell_length_b                   9.2251(3)
_cell_length_c                   10.2483(3)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6000
_cell_measurement_theta_min      4.8850
_cell_volume                     685.68(5)
_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 0.9837
_diffrn_measured_fraction_theta_max 0.7972
_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     23.00  90.00   1.00    1.00    --   36.95-125.00 -30.00   67
  2  \w     10.00 105.00   1.00    1.00    --   36.95  77.00-150.00   95
  3  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00   0.00   75
  4  \w    -30.00  54.00   1.00    1.00    --   36.95 -57.00 -30.00   84
  5  \w     18.00 106.00   1.00    1.00    --   36.95  38.00 -30.00   88
  6  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00  60.00   75
  7  \w     23.00  90.00   1.00    1.00    --   36.95-125.00 -90.00   67
  8  \w     20.00 104.00   1.00    1.00    --   36.95  57.00  60.00   84
  9  \w    -30.00  54.00   1.00    1.00    --   36.95 -57.00  90.00   84
 10  \w    -30.00  54.00   1.00    1.00    --   36.95 -57.00-180.00   84
 11  \w     43.00 128.00   1.00    1.00    --  111.00 -50.00-180.00   85
 12  \w     57.00 150.00   1.00    1.00    --  111.00 178.00  30.00   93
 13  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 -30.00   95
 14  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00  90.00   95
 15  \w     41.00 136.00   1.00    1.00    --  111.00 -25.00-180.00   95
 16  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00  60.00   88
 17  \w     92.00 178.00   1.00    1.00    --  111.00  38.00   0.00   86
 18  \w     41.00 157.00   1.00    1.00    --  111.00 -12.00  30.00  116
 19  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 -90.00   75
 20  \w     41.00 136.00   1.00    1.00    --  111.00 -25.00  90.00   95
 21  \w     41.00 116.00   1.00    1.00    --  111.00-111.00-150.00   75
 22  \w     92.00 178.00   1.00    1.00    --  111.00  38.00  30.00   86
 23  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00 -30.00   88
 24  \w     41.00 116.00   1.00    1.00    --  111.00-111.00  60.00   75
 25  \w     92.00 178.00   1.00    1.00    --  111.00  38.00-120.00   86
 26  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 120.00   95
 27  \w     43.00 128.00   1.00    1.00    --  111.00 -50.00 -30.00   85
 28  \w     41.00 116.00   1.00    1.00    --  111.00-111.00 -30.00   75
 29  \w     43.00 138.00   1.00    1.00    --  111.00 -77.00 -90.00   95
 30  \w     92.00 178.00   1.00    1.00    --  111.00  38.00  60.00   86
 31  \w     44.00 131.00   1.00    1.00    --  111.00 -64.00 -90.00   87
 32  \w     42.00 130.00   1.00    1.00    --  111.00 -38.00-120.00   88
 33  \w     57.00 150.00   1.00    1.00    --  111.00 178.00 -30.00   93
 34  \w     42.00 178.00   1.00    1.00    --  111.00   5.00 165.98  136
 35  \w     42.00 146.00   1.00    1.00    --  111.00 -92.00  90.00  104
 36  \w   -104.00 -20.00   1.00    1.00    --  -36.95 -57.00-150.00   84
 37  \w     10.00 105.00   1.00    1.00    --   36.95  77.00  30.00   95
 38  \w     20.00 104.00   1.00    1.00    --   36.95  57.00  30.00   84
 39  \w     10.00 105.00   1.00    1.00    --   36.95  77.00 -30.00   95
 40  \w     10.00 105.00   1.00    1.00    --   36.95  77.00 150.00   95
 41  \w      8.00 108.00   1.00    1.00    --   36.95  19.00-120.00  100
 42  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00-120.00   88
 43  \w     20.00 104.00   1.00    1.00    --   36.95  57.00 120.00   84
 44  \w     10.00 105.00   1.00    1.00    --   36.95  77.00 120.00   95
 45  \w     10.00 105.00   1.00    1.00    --   36.95  77.00-120.00   95
 46  \w     92.00 178.00   1.00    1.00    --  111.00  38.00-150.00   86
 47  \w     92.00 178.00   1.00    1.00    --  111.00  38.00 -60.00   86
 48  \w     92.00 178.00   1.00    1.00    --  111.00  38.00-180.00   86
;
_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      0.1254854000
_diffrn_orient_matrix_UB_12      0.0331538000
_diffrn_orient_matrix_UB_13      0.1483260000
_diffrn_orient_matrix_UB_21      -0.1476545000
_diffrn_orient_matrix_UB_22      -0.0009817000
_diffrn_orient_matrix_UB_23      0.0685837000
_diffrn_orient_matrix_UB_31      -0.0302793000
_diffrn_orient_matrix_UB_32      -0.1848289000
_diffrn_orient_matrix_UB_33      -0.0488215000
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13949
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.7986
_diffrn_reflns_theta_min         4.8960
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71936
_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    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0595P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                4363
_reflns_number_total             4429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao0c01331_si_010.cif
_cod_data_source_block           ban17_42sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_original_cell_volume        685.67(4)
_cod_database_code               4517753
_publcif_datablock.id            {b49adb2c-5c23-4eaa-9b2e-757b3e6d510b}