#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/77/4517747.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4517747
loop_
_publ_author_name
'Liu, Xin'
'Carr, Paul'
'Gardiner, Michael G.'
'Banwell, Martin G.'
'Elbanna, Ahmed H.'
'Khalil, Zeinab G.'
'Capon, Robert J.'
_publ_section_title
;
 Levoglucosenone and Its Pseudoenantiomer iso-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_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_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'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-17
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_audit_update_record
;
2017-02-27 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.26094(4)
_cell_length_b                   9.56903(5)
_cell_length_c                   13.38456(6)
_cell_measurement_reflns_used    19989
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6650
_cell_measurement_theta_min      3.2090
_cell_volume                     1186.116(10)
_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. HÃ¼bschle 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 0.9875
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -36.95 -57.00-120.00   84
  2  ω     18.00 106.00   1.00    1.00    --   36.95  38.00-150.00   88
  3  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00  30.00   88
  4  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 120.00   67
  5  ω    -34.00  66.00   1.00    1.00    --   36.95 -19.00  90.00  100
  6  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 -90.00   75
  7  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 150.00   75
  8  ω     20.00 104.00   1.00    1.00    --   36.95  57.00   0.00   84
  9  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 -90.00   67
 10  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00   0.00   88
 11  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 -30.00   75
 12  ω     41.00 116.00   1.00    2.00    --  111.00-111.00-150.00   75
 13  ω     43.00 138.00   1.00    2.00    --  111.00 -77.00 120.00   95
 14  ω     91.00 178.00   1.00    2.00    --  111.00  64.00 -30.00   87
 15  ω     41.00 136.00   1.00    2.00    --  111.00 -25.00   0.00   95
 16  ω     42.00 146.00   1.00    2.00    --  111.00 -92.00  30.00  104
 17  ω     92.00 178.00   1.00    2.00    --  111.00  38.00 150.00   86
 18  ω    100.00 178.00   1.00    2.00    --  111.00 111.00  90.00   78
 19  ω     42.00 130.00   1.00    2.00    --  111.00 -38.00 150.00   88
 20  ω     57.00 150.00   1.00    2.00    --  111.00 178.00  30.00   93
 21  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00-120.00   85
 22  ω     41.00 116.00   1.00    2.00    --  111.00-111.00   0.00   75
 23  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00 -60.00   87
 24  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00  30.00   87
 25  ω     42.00 130.00   1.00    2.00    --  111.00 -38.00 -30.00   88
 26  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00 -30.00   85
 27  ω     43.00 138.00   1.00    2.00    --  111.00 -77.00 -60.00   95
 28  ω     42.00 146.00   1.00    2.00    --  111.00 -92.00 150.00  104
 29  ω     65.00 178.00   1.00    2.00    --  111.00  12.00 -90.00  113
 30  ω     84.00 178.00   1.00    2.00    --  111.00  77.00-150.00   94
 31  ω     86.00 178.00   1.00    2.00    --  111.00  25.00 -30.00   92
 32  ω     94.00 178.00   1.00    2.00    --  111.00  50.00 120.00   84
 33  ω     41.00 116.00   1.00    2.00    --  111.00-111.00 -60.00   75
 34  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00-120.00   87
 35  ω     41.00 116.00   1.00    2.00    --  111.00-111.00  30.00   75
 36  ω     41.00 116.00   1.00    2.00    --  111.00-111.00  60.00   75
 37  ω    100.00 178.00   1.00    2.00    --  111.00 111.00 -60.00   78
 38  ω    100.00 178.00   1.00    2.00    --  111.00 111.00   0.00   78
 39  ω    100.00 178.00   1.00    2.00    --  111.00 111.00 150.00   78
 40  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00-180.00   85
 41  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00 -90.00   85
 42  ω     92.00 178.00   1.00    2.00    --  111.00  38.00-180.00   86
 43  ω     43.00 128.00   1.00    2.00    --  111.00 -54.00 118.23   85
 44  ω      4.00  33.00   1.00    1.00    --   36.95  89.00 144.60   29
 45  ω      3.00  32.00   1.00    1.00    --   36.95  90.00 -79.06   29
 46  ω    -32.00 106.00   1.00    1.00    --   36.95   0.00-180.00  138
 47  ω     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
 48  ω     10.00 105.00   1.00    1.00    --   36.95  77.00  30.00   95
 49  ω     20.00 104.00   1.00    1.00    --   36.95  57.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358144000
_diffrn_orient_matrix_UB_12      0.0068485000
_diffrn_orient_matrix_UB_13      0.1123435000
_diffrn_orient_matrix_UB_21      0.0156101000
_diffrn_orient_matrix_UB_22      -0.1598935000
_diffrn_orient_matrix_UB_23      0.0073277000
_diffrn_orient_matrix_UB_31      0.1616887000
_diffrn_orient_matrix_UB_32      0.0169536000
_diffrn_orient_matrix_UB_33      0.0241732000
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24123
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.8344
_diffrn_reflns_theta_min         3.3019
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76706
_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    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                2393
_reflns_number_total             2405
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {7b9376af-dd7c-4286-9686-ff0beff9568d}
_cod_data_source_file            ao0c01331_si_011.cif
_cod_data_source_block           ban17_15sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49697(9) 0.10808(9) 0.18875(7) 0.0276(2) Uani 1 1 d . . .
N1 N 0.97072(12) 0.48947(12) 0.11033(9) 0.0320(3) Uani 1 1 d . . .
C1 C 1.03379(15) 0.56673(14) 0.18155(12) 0.0349(3) Uani 1 1 d . . .
H1 H 1.1172 0.6190 0.1638 0.042 Uiso 1 1 calc R . .
O2 O 0.41088(9) 0.27874(10) 0.08998(7) 0.0293(3) Uani 1 1 d . . .
N2 N 0.76673(11) 0.33915(11) 0.07997(8) 0.0272(3) Uani 1 1 d . . .
C2 C 0.98501(15) 0.57560(14) 0.28037(10) 0.0326(3) Uani 1 1 d . . .
H2 H 1.0347 0.6330 0.3270 0.039 Uiso 1 1 calc R . .
O3 O 0.64084(10) 0.18915(10) 0.37924(7) 0.0291(2) Uani 1 1 d . . .
C3 C 0.86445(14) 0.50078(12) 0.31032(9) 0.0276(3) Uani 1 1 d . . .
H3 H 0.8306 0.5050 0.3772 0.033 Uiso 1 1 calc R . .
C4 C 0.79441(13) 0.41886(12) 0.23878(8) 0.0226(3) Uani 1 1 d . . .
C5 C 0.85307(14) 0.42085(13) 0.14044(9) 0.0253(3) Uani 1 1 d . . .
C6 C 0.67127(11) 0.32932(12) 0.23556(8) 0.0221(3) Uani 1 1 d . . .
C7 C 0.66002(12) 0.28314(12) 0.13950(8) 0.0238(3) Uani 1 1 d . . .
C8 C 0.53538(13) 0.19305(13) 0.10674(8) 0.0253(3) Uani 1 1 d . . .
H8 H 0.5602 0.1361 0.0465 0.030 Uiso 1 1 calc R . .
C9 C 0.44096(12) 0.20896(12) 0.25899(9) 0.0261(3) Uani 1 1 d . . .
H9 H 0.3740 0.1634 0.3077 0.031 Uiso 1 1 calc R . .
C10 C 0.56563(12) 0.28216(11) 0.31356(9) 0.0228(3) Uani 1 1 d . . .
H10 H 0.5284 0.3645 0.3517 0.027 Uiso 1 1 calc R . .
C11 C 0.35762(14) 0.31118(13) 0.18974(9) 0.0286(3) Uani 1 1 d . . .
H11A H 0.2522 0.2953 0.1943 0.034 Uiso 1 1 calc R . .
H11B H 0.3786 0.4095 0.2076 0.034 Uiso 1 1 calc R . .
H22 H 0.7966(18) 0.3085(17) 0.0199(13) 0.029(4) Uiso 1 1 d . . .
C12 C 0.58041(17) 0.17629(19) 0.47629(11) 0.0443(4) Uani 1 1 d . . .
H12A H 0.4946 0.1146 0.4743 0.053 Uiso 1 1 calc R . .
H12B H 0.5500 0.2691 0.5013 0.053 Uiso 1 1 calc R . .
C13 C 0.69209(19) 0.1159(3) 0.54330(13) 0.0566(5) Uani 1 1 d . . .
H13A H 0.7236 0.0254 0.5169 0.085 Uiso 1 1 calc R . .
H13B H 0.6514 0.1030 0.6103 0.085 Uiso 1 1 calc R . .
H13C H 0.7749 0.1795 0.5469 0.085 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 102.23(9) . . ?
C5 N1 C1 114.35(12) . . ?
N1 C1 C2 124.38(12) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C8 O2 C11 104.53(9) . . ?
C7 N2 C5 107.26(10) . . ?
C7 N2 H22 127.6(10) . . ?
C5 N2 H22 122.1(10) . . ?
C3 C2 C1 120.13(12) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C12 O3 C10 115.08(9) . . ?
C2 C3 C4 117.76(12) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C5 116.67(12) . . ?
C3 C4 C6 136.77(11) . . ?
C5 C4 C6 106.55(10) . . ?
N1 C5 N2 125.07(11) . . ?
N1 C5 C4 126.67(12) . . ?
N2 C5 C4 108.26(11) . . ?
C7 C6 C4 106.51(10) . . ?
C7 C6 C10 120.59(10) . . ?
C4 C6 C10 132.89(10) . . ?
C6 C7 N2 111.37(10) . . ?
C6 C7 C8 121.24(10) . . ?
N2 C7 C8 127.15(10) . . ?
O1 C8 O2 104.40(9) . . ?
O1 C8 C7 107.24(9) . . ?
O2 C8 C7 109.56(9) . . ?
O1 C8 H8 111.8 . . ?
O2 C8 H8 111.8 . . ?
C7 C8 H8 111.8 . . ?
O1 C9 C10 110.16(9) . . ?
O1 C9 C11 102.19(10) . . ?
C10 C9 C11 111.74(9) . . ?
O1 C9 H9 110.8 . . ?
C10 C9 H9 110.8 . . ?
C11 C9 H9 110.8 . . ?
O3 C10 C6 107.28(9) . . ?
O3 C10 C9 111.98(9) . . ?
C6 C10 C9 107.25(9) . . ?
O3 C10 H10 110.1 . . ?
C6 C10 H10 110.1 . . ?
C9 C10 H10 110.1 . . ?
O2 C11 C9 104.16(9) . . ?
O2 C11 H11A 110.9 . . ?
C9 C11 H11A 110.9 . . ?
O2 C11 H11B 110.9 . . ?
C9 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
O3 C12 C13 108.15(12) . . ?
O3 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O3 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.4115(14) . ?
O1 C9 1.4438(14) . ?
N1 C5 1.3344(16) . ?
N1 C1 1.3403(19) . ?
C1 C2 1.400(2) . ?
C1 H1 0.9500 . ?
O2 C8 1.4325(14) . ?
O2 C11 1.4568(14) . ?
N2 C7 1.3779(14) . ?
N2 C5 1.3805(16) . ?
N2 H22 0.900(17) . ?
C2 C3 1.3856(19) . ?
C2 H2 0.9500 . ?
O3 C12 1.4198(16) . ?
O3 C10 1.4318(14) . ?
C3 C4 1.3972(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4241(16) . ?
C4 C6 1.4271(16) . ?
C6 C7 1.3634(15) . ?
C6 C10 1.5002(14) . ?
C7 C8 1.5060(16) . ?
C8 H8 1.0000 . ?
C9 C10 1.5353(16) . ?
C9 C11 1.5529(17) . ?
C9 H9 1.0000 . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.486(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
loop_
_publcif_info_cif.paper_type
?
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{7b9376af-dd7c-4286-9686-ff0beff9568d} y y y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346689
