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_4517750
_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 rm
_chemical_formula_moiety         'C11 H8 N2 O5'
_chemical_formula_sum            'C11 H8 N2 O5'
_chemical_formula_weight         248.19
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.910(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6724(2)
_cell_length_b                   9.6556(3)
_cell_length_c                   9.4591(4)
_cell_measurement_reflns_used    4687
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4790
_cell_measurement_theta_min      3.8230
_cell_volume                     502.89(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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 0.998
_diffrn_measured_fraction_theta_max 0.925
_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     -1.00  83.00   1.00   12.67    --   15.42  57.00 -30.00   84
  2  \w    -11.00  83.00   1.00   12.67    --   15.42  77.00 150.00   94
  3  \w     -1.00  83.00   1.00   12.67    --   15.42  57.00  60.00   84
  4  \w    -14.00  87.00   1.00   12.67    --   15.42  19.00 -90.00  101
  5  \w     35.00  88.00   1.00   12.67    --   15.42 178.00  60.00   53
  6  \w     35.00  88.00   1.00   12.67    --   15.42 178.00  30.00   53
  7  \w     34.00  88.00   1.00   12.67    --   15.42-178.00-150.00   54
  8  \w     35.00  88.00   1.00   12.67    --   15.42 178.00 -60.00   53
  9  \w    -84.00 -36.00   1.00   12.67    --  -16.59 149.00  -8.00   48
 10  \w    -69.00 -22.00   1.00   12.67    --  -16.59 124.00-172.00   47
 11  \w    -20.00  54.00   1.00   12.67    --   15.42 -99.00 150.00   74
 12  \w    -43.00   8.00   1.00   12.67    --  -16.59  77.00 -90.00   51
;
_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      0.0388538000
_diffrn_orient_matrix_UB_12      0.0617582000
_diffrn_orient_matrix_UB_13      -0.0280749000
_diffrn_orient_matrix_UB_21      0.0424620000
_diffrn_orient_matrix_UB_22      -0.0392818000
_diffrn_orient_matrix_UB_23      -0.0522350000
_diffrn_orient_matrix_UB_31      -0.1152462000
_diffrn_orient_matrix_UB_32      0.0063562000
_diffrn_orient_matrix_UB_33      -0.0495137000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8874
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.239
_diffrn_reflns_theta_min         3.700
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0363P)^2^+0.0835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                2314
_reflns_number_total             2450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01331_si_007.cif
_cod_data_source_block           xl-2-25scaled
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517750
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C11H8N2O5
_reflns_odcompleteness_completeness 99.73
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              46207
_shelx_hkl_checksum              62307
_ins_header
;
TITL XL-2-27scaled in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 0.71073   5.672408   9.655618   9.459084  90.0000 103.9103  90.0000
ZERR    2.00   0.000195   0.000326   0.000358   0.0000   0.0037   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O
UNIT 22.00 16.00 4.00 10.00
TREF
HKLF 4
END
;
_olex2_date_sample_completion    2019-02-22
_olex2_date_sample_data_collection 2019-02-18
_olex2_date_sample_submission    2019-02-20
_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 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.882