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_4517751
_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 rmad
_chemical_formula_moiety         'C11 H10 N2 O3, H O0.5, 1[H4O2]'
_chemical_formula_sum            'C11 H11 N2 O3.5'
_chemical_formula_weight         227.22
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.9944(3)
_cell_length_b                   14.9944(3)
_cell_length_c                   9.21720(10)
_cell_measurement_reflns_used    7676
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6170
_cell_measurement_theta_min      5.8380
_cell_volume                     1794.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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      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 0.999
_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    -84.00 -24.00   1.00    2.17    --  -36.95 -57.00 -60.00   60
  2  \w    -10.00  31.00   1.00    2.17    --  -36.95  38.00  30.00   41
  3  \w     15.00  72.00   1.00    2.17    --   36.95 -99.00-120.00   57
  4  \w     29.00  83.00   1.00    2.17    --   36.95-125.00-180.00   54
  5  \w     33.00 105.00   1.00    2.17    --   36.95  38.00 -60.00   72
  6  \w     30.00  90.00   1.00    2.17    --   36.95-125.00  30.00   60
  7  \w     30.00  55.00   1.00    2.17    --   36.95-125.00  90.00   25
  8  \w     58.00  83.00   1.00    2.17    --   36.95-125.00  90.00   25
  9  \w    133.00 172.00   1.00    8.67    --  111.00  64.00-120.00   39
 10  \w    120.00 158.00   1.00    8.67    --  111.00  77.00   0.00   38
 11  \w     97.00 130.00   1.00    8.67    --  111.00  64.00-120.00   33
 12  \w     55.00 136.00   1.00    8.67    --  111.00 -25.00 -60.00   81
 13  \w    133.00 162.00   1.00    8.67    --  111.00  50.00  90.00   29
 14  \w    113.00 172.00   1.00    8.67    --  111.00 111.00 -30.00   59
 15  \w    104.00 131.00   1.00    8.67    --  111.00 -77.00 150.00   27
 16  \w     61.00  92.00   1.00    8.67    --  111.00 -77.00 150.00   31
 17  \w     90.00 122.00   1.00    8.67    --  111.00 -38.00  30.00   32
 18  \w    136.00 162.00   1.00    8.67    --  111.00  25.00 -90.00   26
 19  \w     86.00 121.00   1.00    8.67    --  111.00  25.00 -90.00   35
 20  \w    141.00 173.00   1.00    8.67    --  111.00  50.00 -90.00   32
 21  \w     56.00  94.00   1.00    8.67    --  111.00-111.00 -90.00   38
 22  \w     45.00  98.00   1.00    8.67    --  111.00-111.00  30.00   53
 23  \w     94.00 123.00   1.00    8.67    --  111.00  50.00 -90.00   29
 24  \w     54.00 101.00   1.00    8.67    --  111.00-111.00  90.00   47
 25  \w     57.00  91.00   1.00    8.67    --  111.00 -77.00 120.00   34
 26  \w    101.00 127.00   1.00    8.67    --  111.00  50.00  90.00   26
 27  \w     51.00  77.00   1.00    8.67    --  111.00 -38.00  30.00   26
 28  \w     96.00 160.00   1.00    8.67    --  111.00  38.00 -30.00   64
 29  \w     97.00 144.00   1.00    8.67    --  111.00  38.00  60.00   47
 30  \w    150.00 175.00   1.00    8.67    --  111.00  38.00  60.00   25
 31  \w     84.00 135.00   1.00    8.67    --  111.00 -77.00 -30.00   51
 32  \w     43.00 106.00   1.00    8.67    --  111.00 -92.00 120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0676344000
_diffrn_orient_matrix_UB_12      0.1154144000
_diffrn_orient_matrix_UB_13      -0.0349168000
_diffrn_orient_matrix_UB_21      -0.0656272000
_diffrn_orient_matrix_UB_22      -0.0139891000
_diffrn_orient_matrix_UB_23      -0.1357795000
_diffrn_orient_matrix_UB_31      -0.0720884000
_diffrn_orient_matrix_UB_32      0.0234956000
_diffrn_orient_matrix_UB_33      0.0909384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0169
_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       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.740
_diffrn_reflns_theta_min         3.404
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       needle
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0583P)^2^+0.2400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2394
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01331_si_009.cif
_cod_data_source_block           xl-4-60-1scaledredo2
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_original_cell_volume        1794.68(7)
_cod_original_formula_sum        'C11 H11 N2 O3.50'
_cod_database_code               4517751
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C11H16N2O6
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C9(H9), C10(H10)
;
_shelx_res_checksum              30991
_shelx_hkl_checksum              93275
_shelx_fab_checksum              83616
_ins_header
;
TITL XL-4-60-1scaledredo2 in P3(1)21 
REM P3(1)21 (#152 in standard setting)
CELL 1.54184  14.994401  14.994401   9.217234  90.0000  90.0000 120.0000
ZERR    5.00   0.000262   0.000262   0.000141   0.0000   0.0000   0.0000
LATT -1
SYMM -y, x-y, z+1/3 
SYMM -x+y,-x, z+2/3 
SYMM  y, x,-z 
SYMM  x-y,-y,-z+2/3 
SYMM -x,-x+y,-z+1/3 
SFAC C H N O
UNIT 55.00 80.00 10.00 30.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-04-03
_olex2_date_sample_submission    2019-04-03
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_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 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.847