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_4517749
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6892(4)
_cell_length_b                   9.8837(4)
_cell_length_c                   10.8874(4)
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.3650
_cell_measurement_theta_min      4.1190
_cell_volume                     1042.63(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.895
_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    -11.00  83.00   1.00    7.19    --   15.42  77.00-180.00   94
  2  \w    -11.00  83.00   1.00    7.19    --   15.42  77.00  90.00   94
  3  \w     34.00  67.00   1.00    7.19    --   15.42-178.00 -30.00   33
  4  \w    -20.00  54.00   1.00    7.19    --   15.42 -99.00  90.00   74
;
_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      0.0125447000
_diffrn_orient_matrix_UB_12      0.0487249000
_diffrn_orient_matrix_UB_13      0.0464776000
_diffrn_orient_matrix_UB_21      0.0260002000
_diffrn_orient_matrix_UB_22      0.0454338000
_diffrn_orient_matrix_UB_23      -0.0448024000
_diffrn_orient_matrix_UB_31      -0.0673091000
_diffrn_orient_matrix_UB_32      0.0266483000
_diffrn_orient_matrix_UB_33      -0.0086274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6775
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.165
_diffrn_reflns_theta_min         3.489
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99125
_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    1.581
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0393P)^2^+0.1010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                2263
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01331_si_002.cif
_cod_data_source_block           xl-1-109scaled
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517749
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C11H8N2O5
_reflns_odcompleteness_completeness 98.89
_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              45209
_shelx_hkl_checksum              47675
_ins_header
;
TITL XL-1-109scaled in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 0.71073   9.689201   9.883702  10.887416  90.0000  90.0000  90.0000
ZERR    3.00   0.000387   0.000385   0.000397   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N O
UNIT 33.00 24.00 6.00 15.00
TREF
HKLF 4
END
;
_olex2_date_sample_completion    2019-02-21
_olex2_date_sample_data_collection 2019-02-18
_olex2_date_sample_submission    2019-02-13
_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 1.081
_oxdiff_exptl_absorpt_empirical_full_min 0.920