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_4517752
_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_moiety         'C11 H8 N2 O3'
_chemical_formula_sum            'C11 H8 N2 O3'
_chemical_formula_weight         216.19
_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   mixed
_audit_creation_date             2020-03-13
_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                   4.74660(10)
_cell_length_b                   12.1979(2)
_cell_length_c                   16.5531(3)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.7880
_cell_measurement_theta_min      4.4620
_cell_volume                     958.40(3)
_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    '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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -32.00  56.00   1.00    2.50    --   37.20 -38.00 -30.00   88
  2  \w      1.00  76.00   1.00    2.50    --   37.20 -99.00  30.00   75
  3  \w    -30.00  54.00   1.00    2.50    --   37.20 -57.00  90.00   84
  4  \w     20.00 104.00   1.00    2.50    --   37.20  57.00-120.00   84
  5  \w      1.00  76.00   1.00    2.50    --   37.20 -99.00 120.00   75
  6  \w      1.00  76.00   1.00    2.50    --   37.20 -99.00-180.00   75
  7  \w     21.00 105.00   1.00    2.50    --   37.20  54.00  53.00   84
  8  \w     23.00  91.00   1.00    2.50    --   37.20-125.00 -60.00   68
  9  \w     20.00 104.00   1.00    2.50    --   37.20  57.00 -30.00   84
 10  \w    -32.00  56.00   1.00    2.50    --   37.20 -38.00 120.00   88
 11  \w     23.00  91.00   1.00    2.50    --   37.20-125.00 120.00   68
 12  \w     91.00 178.00   1.00   11.00    --  111.00  64.00 -60.00   87
 13  \w     41.00 116.00   1.00   11.00    --  111.00-111.00  90.00   75
 14  \w     57.00 150.00   1.00   11.00    --  111.00 178.00  30.00   93
 15  \w     41.00 116.00   1.00   11.00    --  111.00-111.00   0.00   75
 16  \w     44.00 131.00   1.00   11.00    --  111.00 -64.00  60.00   87
 17  \w     41.00 132.00   1.00   11.00    --  111.00 -30.00 125.92   91
 18  \w     41.00 157.00   1.00   11.00    --  111.00 -12.00 -90.00  116
 19  \w    105.00 131.00   1.00   11.00    --  111.00 -92.00  60.00   26
 20  \w     60.00  93.00   1.00   11.00    --  111.00 -77.00   0.00   33
 21  \w     95.00 124.00   1.00   11.00    --  111.00 -77.00   0.00   29
 22  \w     43.00  79.00   1.00   11.00    --  111.00 -92.00  60.00   36
 23  \w     50.00  87.00   1.00   11.00    --  111.00 -50.00 -30.00   37
 24  \w     66.00 124.00   1.00   11.00    --  111.00 -38.00  30.00   58
 25  \w     96.00 149.00   1.00   11.00    --  111.00 -15.00  23.38   53
 26  \w     45.00 131.00   1.00   11.00    --  111.00 -64.00-180.00   86
 27  \w     53.00  79.00   1.00   11.00    --  111.00-111.00 -90.00   26
 28  \w     49.00 109.00   1.00   11.00    --  111.00 -25.00 -60.00   60
 29  \w     98.00 124.00   1.00   11.00    --  111.00 -77.00 -60.00   26
 30  \w    140.00 166.00   1.00   11.00    --  111.00  38.00   0.00   26
 31  \w     83.00 112.00   1.00   11.00    --  111.00-111.00 -90.00   29
 32  \w     86.00 112.00   1.00   11.00    --  111.00-111.00 150.00   26
 33  \w     44.00  95.00   1.00   11.00    --  111.00 -50.00 -90.00   51
 34  \w     49.00  74.00   1.00   11.00    --  111.00 -77.00 -60.00   25
 35  \w     95.00 128.00   1.00   11.00    --  111.00  25.00-120.00   33
 36  \w     60.00  86.00   1.00   11.00    --  111.00 -25.00  60.00   26
 37  \w    106.00 132.00   1.00   11.00    --  111.00 -25.00  60.00   26
 38  \w     95.00 153.00   1.00   11.00    --  111.00  50.00-120.00   58
 39  \w     66.00  93.00   1.00   11.00    --  111.00 -15.00  23.38   27
 40  \w     84.00 115.00   1.00   11.00    --  111.00-111.00-150.00   31
 41  \w     95.00 121.00   1.00   11.00    --  111.00  50.00-150.00   26
 42  \w     93.00 172.00   1.00   11.00    --  111.00  38.00  90.00   79
 43  \w    120.00 146.00   1.00   11.00    --  111.00  25.00  90.00   26
 44  \w     86.00 112.00   1.00   11.00    --  111.00 -77.00-120.00   26
 45  \w     53.00 112.00   1.00   11.00    --  111.00-100.00-162.05   59
;
_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      0.0122995000
_diffrn_orient_matrix_UB_12      -0.0993924000
_diffrn_orient_matrix_UB_13      -0.0572203000
_diffrn_orient_matrix_UB_21      0.3149809000
_diffrn_orient_matrix_UB_22      -0.0148771000
_diffrn_orient_matrix_UB_23      0.0194802000
_diffrn_orient_matrix_UB_31      -0.0769862000
_diffrn_orient_matrix_UB_32      -0.0764925000
_diffrn_orient_matrix_UB_33      0.0707955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.091
_diffrn_reflns_theta_min         4.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71685
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0614P)^2^+0.0229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1846
_reflns_number_total             1931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01331_si_012.cif
_cod_data_source_block           xl-1-114_scale
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517752
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H18 N2 O3'
_reflns_odcompleteness_completeness 98.75
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              40651
_shelx_hkl_checksum              46546
_ins_header
;
TITL XL-1-114_scale in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   4.746577  12.197901  16.553098  90.0000  90.0000  90.0000
ZERR    3.00   0.000090   0.000219   0.000299   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 54.00 6.00 9.00
TREF
HKLF 4
END
;
_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 2.491
_oxdiff_exptl_absorpt_empirical_full_min 0.588