#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/77/4517755.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_4517755
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            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_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'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-09
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_audit_update_record
;
2017-02-24 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 102.5485(8)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   9.90829(8)
_cell_length_b                   9.74229(7)
_cell_length_c                   19.67523(17)
_cell_measurement_reflns_used    26099
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7630
_cell_measurement_theta_min      4.6090
_cell_volume                     1853.87(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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 0.9886
_diffrn_measured_fraction_theta_max 0.9980
_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 -60.00   84
  2  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00 -30.00   88
  3  ω     20.00 104.00   1.00    1.00    --   36.95  57.00   0.00   84
  4  ω     24.00  91.00   1.00    1.00    --   36.95-126.00-129.00   67
  5  ω     10.00 105.00   1.00    1.00    --   36.95  77.00  60.00   95
  6  ω     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
  7  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00-120.00   75
  8  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 -60.00   75
  9  ω    -34.00  66.00   1.00    1.00    --   36.95 -19.00-120.00  100
 10  ω     23.00  90.00   1.00    1.00    --   36.95-125.00-180.00   67
 11  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00  60.00   88
 12  ω      2.00  29.00   1.00    1.00    --   36.95  91.00 100.71   27
 13  ω     20.00 104.00   1.00    1.00    --   36.95  57.00-180.00   84
 14  ω     44.00 131.00   1.00    1.00    --  111.00 -64.00  30.00   87
 15  ω     92.00 178.00   1.00    1.00    --  111.00  38.00   0.00   86
 16  ω     41.00 116.00   1.00    1.00    --  111.00-111.00-150.00   75
 17  ω     94.00 178.00   1.00    1.00    --  111.00  50.00 -90.00   84
 18  ω     44.00 131.00   1.00    1.00    --  111.00 -64.00 150.00   87
 19  ω     92.00 178.00   1.00    1.00    --  111.00  38.00  90.00   86
 20  ω     43.00 128.00   1.00    1.00    --  111.00 -50.00 -90.00   85
 21  ω     41.00 116.00   1.00    1.00    --  111.00-111.00  30.00   75
 22  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00-180.00   88
 23  ω     41.00 157.00   1.00    1.00    --  111.00 -12.00 120.00  116
 24  ω     41.00 116.00   1.00    1.00    --  111.00-111.00  60.00   75
 25  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00  60.00   95
 26  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00  90.00   88
 27  ω     94.00 178.00   1.00    1.00    --  111.00  50.00-120.00   84
 28  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 -90.00   75
 29  ω     94.00 178.00   1.00    1.00    --  111.00  50.00 -30.00   84
 30  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00 -30.00   88
 31  ω     44.00 131.00   1.00    1.00    --  111.00 -64.00 -90.00   87
 32  ω     92.00 178.00   1.00    1.00    --  111.00  38.00 -30.00   86
 33  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 -60.00   75
 34  ω     91.00 178.00   1.00    1.00    --  111.00  64.00  30.00   87
 35  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 120.00   75
 36  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 150.00   75
 37  ω     94.00 178.00   1.00    1.00    --  111.00  50.00 120.00   84
 38  ω    100.00 178.00   1.00    1.00    --  111.00 111.00-120.00   78
 39  ω     84.00 178.00   1.00    1.00    --  111.00  77.00-150.00   94
 40  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 -90.00   95
 41  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 150.00   95
 42  ω     41.00 116.00   1.00    1.00    --  111.00-111.00-180.00   75
 43  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00 -90.00   88
 44  ω     94.00 178.00   1.00    1.00    --  111.00  50.00 150.00   84
 45  ω     42.00 146.00   1.00    1.00    --  111.00 -92.00 -60.00  104
 46  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 -30.00   95
 47  ω     41.00 157.00   1.00    1.00    --  111.00 -12.00 -60.00  116
 48  ω    -56.00  18.00   1.00    1.00    --  -36.95  38.00-120.00   74
;
_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      -0.0670799000
_diffrn_orient_matrix_UB_12      -0.1423575000
_diffrn_orient_matrix_UB_13      0.0012105000
_diffrn_orient_matrix_UB_21      0.0455460000
_diffrn_orient_matrix_UB_22      -0.0028516000
_diffrn_orient_matrix_UB_23      0.0800147000
_diffrn_orient_matrix_UB_31      -0.1370825000
_diffrn_orient_matrix_UB_32      0.0687417000
_diffrn_orient_matrix_UB_33      0.0057661000
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37890
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.8902
_diffrn_reflns_theta_min         2.3005
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.583
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+0.0670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                7251
_reflns_number_total             7371
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {570cea36-6994-4c8b-b621-291524caae51}
_cod_data_source_file            ao0c01331_si_004.cif
_cod_data_source_block           ban17_12sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_database_code               4517755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.24482(10) 0.08832(11) 0.45252(5) 0.0291(2) Uani 1 1 d . . .
N1 N 0.50384(11) 0.08544(13) 0.36789(6) 0.0241(2) Uani 1 1 d . . .
H91 H 0.4723(19) 0.165(2) 0.3438(10) 0.029 Uiso 1 1 d . . .
C1 C 0.30164(14) -0.14251(16) 0.48573(7) 0.0275(3) Uani 1 1 d . . .
H1 H 0.2525 -0.2110 0.5095 0.033 Uiso 1 1 calc R . .
O2 O 0.23378(10) -0.12827(11) 0.41301(5) 0.0275(2) Uani 1 1 d . . .
N2 N 0.74642(12) 0.11231(13) 0.37099(6) 0.0280(3) Uani 1 1 d . . .
C2 C 0.45224(14) -0.18450(15) 0.49096(7) 0.0273(3) Uani 1 1 d . . .
H2A H 0.5041 -0.1803 0.5400 0.033 Uiso 1 1 calc R . .
H2B H 0.4572 -0.2794 0.4737 0.033 Uiso 1 1 calc R . .
C3 C 0.51256(14) -0.08547(14) 0.44696(7) 0.0236(3) Uani 1 1 d . . .
C4 C 0.42878(13) 0.00177(14) 0.40270(7) 0.0218(3) Uani 1 1 d . . .
C5 C 0.27513(14) 0.00591(15) 0.39796(7) 0.0248(3) Uani 1 1 d . . .
H5 H 0.2240 0.0381 0.3512 0.030 Uiso 1 1 calc R . .
C6 C 0.28777(15) 0.00371(17) 0.51386(7) 0.0304(3) Uani 1 1 d . . .
H6A H 0.2178 0.0058 0.5429 0.036 Uiso 1 1 calc R . .
H6B H 0.3773 0.0358 0.5422 0.036 Uiso 1 1 calc R . .
C7 C 0.78311(14) -0.10242(16) 0.47229(7) 0.0280(3) Uani 1 1 d . . .
H7 H 0.7967 -0.1734 0.5062 0.034 Uiso 1 1 calc R . .
C8 C 0.89386(14) -0.04064(17) 0.45168(8) 0.0309(3) Uani 1 1 d . . .
H8 H 0.9854 -0.0698 0.4715 0.037 Uiso 1 1 calc R . .
C9 C 0.87190(14) 0.06421(17) 0.40190(8) 0.0310(3) Uani 1 1 d . . .
H9 H 0.9505 0.1038 0.3892 0.037 Uiso 1 1 calc R . .
C10 C 0.64094(14) 0.05130(14) 0.39151(7) 0.0236(3) Uani 1 1 d . . .
C11 C 0.65068(14) -0.05596(14) 0.44110(7) 0.0240(3) Uani 1 1 d . . .
O21 O 1.01186(11) 0.46661(12) 0.37600(6) 0.0332(2) Uani 1 1 d . . .
N21 N 0.69100(12) 0.37659(13) 0.30768(6) 0.0255(2) Uani 1 1 d . . .
H21 H 0.709(2) 0.298(2) 0.3172(10) 0.031 Uiso 1 1 d . . .
C21 C 0.97051(15) 0.68218(17) 0.31879(7) 0.0311(3) Uani 1 1 d . . .
H21A H 1.0339 0.7596 0.3138 0.037 Uiso 1 1 calc R . .
O22 O 0.98470(10) 0.56997(14) 0.27185(5) 0.0347(2) Uani 1 1 d . . .
N22 N 0.45508(12) 0.37907(14) 0.32000(6) 0.0270(2) Uani 1 1 d . . .
C22 C 0.81998(15) 0.73021(16) 0.30243(7) 0.0299(3) Uani 1 1 d . . .
H22A H 0.8043 0.7964 0.3381 0.036 Uiso 1 1 calc R . .
H22B H 0.7975 0.7759 0.2564 0.036 Uiso 1 1 calc R . .
C23 C 0.73083(14) 0.60556(15) 0.30225(7) 0.0249(3) Uani 1 1 d . . .
C24 C 0.78628(14) 0.47723(16) 0.30268(7) 0.0250(3) Uani 1 1 d . . .
C25 C 0.93742(14) 0.45729(17) 0.30596(8) 0.0293(3) Uani 1 1 d . . .
H25 H 0.9555 0.3681 0.2844 0.035 Uiso 1 1 calc R . .
C26 C 1.01683(15) 0.61247(16) 0.39020(7) 0.0307(3) Uani 1 1 d . . .
H26A H 1.1118 0.6411 0.4129 0.037 Uiso 1 1 calc R . .
H26B H 0.9538 0.6367 0.4211 0.037 Uiso 1 1 calc R . .
C27 C 0.47938(15) 0.67090(16) 0.31408(7) 0.0270(3) Uani 1 1 d . . .
H27 H 0.4863 0.7680 0.3124 0.032 Uiso 1 1 calc R . .
C28 C 0.35921(16) 0.60769(17) 0.32245(8) 0.0316(3) Uani 1 1 d . . .
H28 H 0.2814 0.6618 0.3262 0.038 Uiso 1 1 calc R . .
C29 C 0.35141(14) 0.46370(18) 0.32537(8) 0.0304(3) Uani 1 1 d . . .
H29 H 0.2673 0.4240 0.3315 0.037 Uiso 1 1 calc R . .
C30 C 0.57029(14) 0.44181(15) 0.31212(7) 0.0233(3) Uani 1 1 d . . .
C31 C 0.59049(14) 0.58634(15) 0.30819(6) 0.0228(3) Uani 1 1 d . . .
O41 O 0.77349(11) 0.56980(12) 0.05080(5) 0.0310(2) Uani 1 1 d . . .
N41 N 0.50868(12) 0.56376(13) 0.13225(6) 0.0252(2) Uani 1 1 d . . .
H92 H 0.538(2) 0.643(2) 0.1541(10) 0.030 Uiso 1 1 d . . .
C41 C 0.72301(15) 0.33764(16) 0.01936(7) 0.0283(3) Uani 1 1 d . . .
H41 H 0.7751 0.2697 -0.0031 0.034 Uiso 1 1 calc R . .
O42 O 0.78750(10) 0.35508(11) 0.09244(5) 0.0284(2) Uani 1 1 d . . .
N42 N 0.26535(13) 0.58139(14) 0.12802(7) 0.0288(3) Uani 1 1 d . . .
C42 C 0.57236(15) 0.29257(15) 0.01246(7) 0.0283(3) Uani 1 1 d . . .
H42A H 0.5224 0.2957 -0.0369 0.034 Uiso 1 1 calc R . .
H42B H 0.5684 0.1976 0.0298 0.034 Uiso 1 1 calc R . .
C43 C 0.50824(14) 0.39063(15) 0.05520(7) 0.0252(3) Uani 1 1 d . . .
C44 C 0.58786(14) 0.48159(15) 0.09895(7) 0.0238(3) Uani 1 1 d . . .
C45 C 0.74181(14) 0.48936(15) 0.10542(7) 0.0260(3) Uani 1 1 d . . .
H45 H 0.7902 0.5242 0.1522 0.031 Uiso 1 1 calc R . .
C46 C 0.73425(16) 0.48377(17) -0.01008(7) 0.0322(3) Uani 1 1 d . . .
H46A H 0.8052 0.4867 -0.0385 0.039 Uiso 1 1 calc R . .
H46B H 0.6445 0.5134 -0.0391 0.039 Uiso 1 1 calc R . .
C47 C 0.23785(15) 0.36346(16) 0.02945(7) 0.0299(3) Uani 1 1 d . . .
H47 H 0.2272 0.2915 -0.0039 0.036 Uiso 1 1 calc R . .
C48 C 0.12434(15) 0.42091(17) 0.04955(8) 0.0330(3) Uani 1 1 d . . .
H48 H 0.0341 0.3874 0.0303 0.040 Uiso 1 1 calc R . .
C49 C 0.14217(15) 0.52761(17) 0.09795(8) 0.0323(3) Uani 1 1 d . . .
H49 H 0.0621 0.5645 0.1104 0.039 Uiso 1 1 calc R . .
C50 C 0.37314(14) 0.52456(15) 0.10855(7) 0.0247(3) Uani 1 1 d . . .
C51 C 0.36866(14) 0.41567(15) 0.06014(7) 0.0252(3) Uani 1 1 d . . .
O61 O -0.03180(10) 0.92585(11) 0.11972(5) 0.0289(2) Uani 1 1 d . . .
N61 N 0.29764(12) 0.84915(13) 0.18126(6) 0.0241(2) Uani 1 1 d . . .
H61 H 0.2873(19) 0.777(2) 0.1713(10) 0.029 Uiso 1 1 d . . .
C61 C -0.00024(15) 1.12467(17) 0.19062(8) 0.0300(3) Uani 1 1 d . . .
H61A H -0.0675 1.1930 0.2019 0.036 Uiso 1 1 calc R . .
O62 O -0.00272(10) 0.99938(12) 0.23028(5) 0.0315(2) Uani 1 1 d . . .
N62 N 0.53283(12) 0.87288(14) 0.17074(6) 0.0266(2) Uani 1 1 d . . .
C62 C 0.14632(14) 1.18473(16) 0.20594(7) 0.0286(3) Uani 1 1 d . . .
H62A H 0.1526 1.2602 0.1731 0.034 Uiso 1 1 calc R . .
H62B H 0.1704 1.2215 0.2540 0.034 Uiso 1 1 calc R . .
C63 C 0.24296(14) 1.07039(16) 0.19751(7) 0.0239(3) Uani 1 1 d . . .
C64 C 0.19649(14) 0.93785(15) 0.19098(7) 0.0231(3) Uani 1 1 d . . .
C65 C 0.04843(13) 0.90324(16) 0.18782(7) 0.0257(3) Uani 1 1 d . . .
H65 H 0.0382 0.8069 0.2035 0.031 Uiso 1 1 calc R . .
C66 C -0.04768(14) 1.07335(16) 0.11495(8) 0.0297(3) Uani 1 1 d . . .
H66A H -0.1453 1.0986 0.0957 0.036 Uiso 1 1 calc R . .
H66B H 0.0106 1.1128 0.0849 0.036 Uiso 1 1 calc R . .
C67 C 0.48860(15) 1.16025(16) 0.18756(7) 0.0262(3) Uani 1 1 d . . .
H67 H 0.4755 1.2559 0.1930 0.031 Uiso 1 1 calc R . .
C68 C 0.61252(15) 1.10865(17) 0.17654(8) 0.0295(3) Uani 1 1 d . . .
H68 H 0.6862 1.1697 0.1744 0.035 Uiso 1 1 calc R . .
C69 C 0.63010(14) 0.96697(17) 0.16860(8) 0.0295(3) Uani 1 1 d . . .
H69 H 0.7167 0.9359 0.1612 0.035 Uiso 1 1 calc R . .
C70 C 0.41341(13) 0.92461(14) 0.18046(6) 0.0220(3) Uani 1 1 d . . .
C71 C 0.38391(13) 1.06594(15) 0.19036(6) 0.0230(3) Uani 1 1 d . . .
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
C5 O1 C6 103.63(11) . . ?
C10 N1 C4 106.74(12) . . ?
C10 N1 H91 124.9(11) . . ?
C4 N1 H91 126.1(11) . . ?
O2 C1 C2 109.19(10) . . ?
O2 C1 C6 101.95(11) . . ?
C2 C1 C6 112.58(12) . . ?
O2 C1 H1 110.9 . . ?
C2 C1 H1 110.9 . . ?
C6 C1 H1 110.9 . . ?
C5 O2 C1 101.60(10) . . ?
C10 N2 C9 114.51(13) . . ?
C3 C2 C1 107.08(11) . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C11 106.53(12) . . ?
C4 C3 C2 120.33(12) . . ?
C11 C3 C2 133.12(12) . . ?
C3 C4 N1 111.48(12) . . ?
C3 C4 C5 121.59(12) . . ?
N1 C4 C5 126.85(12) . . ?
O2 C5 O1 104.13(10) . . ?
O2 C5 C4 107.22(11) . . ?
O1 C5 C4 110.15(11) . . ?
O2 C5 H5 111.7 . . ?
O1 C5 H5 111.7 . . ?
C4 C5 H5 111.7 . . ?
O1 C6 C1 105.03(11) . . ?
O1 C6 H6A 110.7 . . ?
C1 C6 H6A 110.7 . . ?
O1 C6 H6B 110.7 . . ?
C1 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C11 117.26(14) . . ?
C8 C7 H7 121.4 . . ?
C11 C7 H7 121.4 . . ?
C7 C8 C9 120.59(13) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N2 C9 C8 124.00(13) . . ?
N2 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
N2 C10 N1 124.64(13) . . ?
N2 C10 C11 126.41(13) . . ?
N1 C10 C11 108.94(12) . . ?
C7 C11 C10 117.24(13) . . ?
C7 C11 C3 136.42(13) . . ?
C10 C11 C3 106.31(11) . . ?
C25 O21 C26 103.85(11) . . ?
C30 N21 C24 107.13(12) . . ?
C30 N21 H21 125.4(14) . . ?
C24 N21 H21 125.3(14) . . ?
O22 C21 C22 108.67(11) . . ?
O22 C21 C26 101.36(12) . . ?
C22 C21 C26 114.28(12) . . ?
O22 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
C26 C21 H21A 110.7 . . ?
C25 O22 C21 101.15(10) . . ?
C30 N22 C29 114.69(13) . . ?
C23 C22 C21 107.43(12) . . ?
C23 C22 H22A 110.2 . . ?
C21 C22 H22A 110.2 . . ?
C23 C22 H22B 110.2 . . ?
C21 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C24 C23 C31 106.04(13) . . ?
C24 C23 C22 120.34(13) . . ?
C31 C23 C22 133.35(14) . . ?
C23 C24 N21 111.76(12) . . ?
C23 C24 C25 121.10(13) . . ?
N21 C24 C25 126.75(14) . . ?
O21 C25 O22 104.76(11) . . ?
O21 C25 C24 109.74(11) . . ?
O22 C25 C24 108.02(12) . . ?
O21 C25 H25 111.4 . . ?
O22 C25 H25 111.4 . . ?
C24 C25 H25 111.4 . . ?
O21 C26 C21 105.44(12) . . ?
O21 C26 H26A 110.7 . . ?
C21 C26 H26A 110.7 . . ?
O21 C26 H26B 110.7 . . ?
C21 C26 H26B 110.7 . . ?
H26A C26 H26B 108.8 . . ?
C28 C27 C31 117.47(14) . . ?
C28 C27 H27 121.3 . . ?
C31 C27 H27 121.3 . . ?
C27 C28 C29 120.38(14) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
N22 C29 C28 124.11(14) . . ?
N22 C29 H29 117.9 . . ?
C28 C29 H29 117.9 . . ?
N22 C30 N21 125.07(13) . . ?
N22 C30 C31 126.34(13) . . ?
N21 C30 C31 108.58(12) . . ?
C27 C31 C30 117.01(13) . . ?
C27 C31 C23 136.43(14) . . ?
C30 C31 C23 106.47(12) . . ?
C45 O41 C46 104.10(11) . . ?
C50 N41 C44 106.94(12) . . ?
C50 N41 H92 126.0(12) . . ?
C44 N41 H92 124.5(12) . . ?
O42 C41 C42 109.39(11) . . ?
O42 C41 C46 102.17(11) . . ?
C42 C41 C46 112.18(12) . . ?
O42 C41 H41 110.9 . . ?
C42 C41 H41 110.9 . . ?
C46 C41 H41 110.9 . . ?
C45 O42 C41 101.33(10) . . ?
C50 N42 C49 114.87(13) . . ?
C43 C42 C41 106.87(12) . . ?
C43 C42 H42A 110.3 . . ?
C41 C42 H42A 110.3 . . ?
C43 C42 H42B 110.3 . . ?
C41 C42 H42B 110.3 . . ?
H42A C42 H42B 108.6 . . ?
C44 C43 C51 106.40(12) . . ?
C44 C43 C42 120.70(12) . . ?
C51 C43 C42 132.88(13) . . ?
C43 C44 N41 111.48(12) . . ?
C43 C44 C45 121.58(13) . . ?
N41 C44 C45 126.89(12) . . ?
O41 C45 O42 103.88(11) . . ?
O41 C45 C44 110.52(11) . . ?
O42 C45 C44 107.12(11) . . ?
O41 C45 H45 111.7 . . ?
O42 C45 H45 111.7 . . ?
C44 C45 H45 111.7 . . ?
O41 C46 C41 104.56(11) . . ?
O41 C46 H46A 110.8 . . ?
C41 C46 H46A 110.8 . . ?
O41 C46 H46B 110.8 . . ?
C41 C46 H46B 110.8 . . ?
H46A C46 H46B 108.9 . . ?
C48 C47 C51 117.49(14) . . ?
C48 C47 H47 121.3 . . ?
C51 C47 H47 121.3 . . ?
C47 C48 C49 120.30(14) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
N42 C49 C48 124.07(14) . . ?
N42 C49 H49 118.0 . . ?
C48 C49 H49 118.0 . . ?
N42 C50 N41 124.89(13) . . ?
N42 C50 C51 126.42(13) . . ?
N41 C50 C51 108.69(12) . . ?
C47 C51 C50 116.84(13) . . ?
C47 C51 C43 136.66(13) . . ?
C50 C51 C43 106.48(12) . . ?
C65 O61 C66 104.27(11) . . ?
C70 N61 C64 107.72(12) . . ?
C70 N61 H61 125.8(15) . . ?
C64 N61 H61 125.5(15) . . ?
O62 C61 C62 109.94(12) . . ?
O62 C61 C66 102.06(12) . . ?
C62 C61 C66 112.95(11) . . ?
O62 C61 H61A 110.5 . . ?
C62 C61 H61A 110.5 . . ?
C66 C61 H61A 110.5 . . ?
C65 O62 C61 100.86(10) . . ?
C69 N62 C70 114.35(13) . . ?
C63 C62 C61 107.14(12) . . ?
C63 C62 H62A 110.3 . . ?
C61 C62 H62A 110.3 . . ?
C63 C62 H62B 110.3 . . ?
C61 C62 H62B 110.3 . . ?
H62A C62 H62B 108.5 . . ?
C64 C63 C71 106.11(12) . . ?
C64 C63 C62 120.07(12) . . ?
C71 C63 C62 133.73(14) . . ?
C63 C64 N61 111.57(12) . . ?
C63 C64 C65 121.66(13) . . ?
N61 C64 C65 126.48(13) . . ?
O61 C65 O62 104.77(11) . . ?
O61 C65 C64 110.36(11) . . ?
O62 C65 C64 107.43(11) . . ?
O61 C65 H65 111.3 . . ?
O62 C65 H65 111.3 . . ?
C64 C65 H65 111.3 . . ?
O61 C66 C61 104.66(12) . . ?
O61 C66 H66A 110.8 . . ?
C61 C66 H66A 110.8 . . ?
O61 C66 H66B 110.8 . . ?
C61 C66 H66B 110.8 . . ?
H66A C66 H66B 108.9 . . ?
C68 C67 C71 117.28(14) . . ?
C68 C67 H67 121.4 . . ?
C71 C67 H67 121.4 . . ?
C67 C68 C69 120.61(14) . . ?
C67 C68 H68 119.7 . . ?
C69 C68 H68 119.7 . . ?
N62 C69 C68 124.23(14) . . ?
N62 C69 H69 117.9 . . ?
C68 C69 H69 117.9 . . ?
N62 C70 N61 124.77(13) . . ?
N62 C70 C71 126.57(13) . . ?
N61 C70 C71 108.65(11) . . ?
C67 C71 C70 116.93(12) . . ?
C67 C71 C63 137.03(14) . . ?
C70 C71 C63 105.95(12) . . ?
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 C5 1.4238(16) . ?
O1 C6 1.4471(18) . ?
N1 C10 1.3775(17) . ?
N1 C4 1.3813(17) . ?
N1 H91 0.93(2) . ?
C1 O2 1.4493(16) . ?
C1 C2 1.5290(18) . ?
C1 C6 1.545(2) . ?
C1 H1 1.0000 . ?
O2 C5 1.4202(17) . ?
N2 C10 1.3386(17) . ?
N2 C9 1.3441(19) . ?
C2 C3 1.5041(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3622(19) . ?
C3 C11 1.4274(18) . ?
C4 C5 1.5055(17) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.387(2) . ?
C7 C11 1.3976(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.4185(19) . ?
O21 C25 1.4176(17) . ?
O21 C26 1.4470(19) . ?
N21 C30 1.3738(18) . ?
N21 C24 1.3794(18) . ?
N21 H21 0.80(2) . ?
C21 O22 1.4575(19) . ?
C21 C22 1.529(2) . ?
C21 C26 1.5381(19) . ?
C21 H21A 1.0000 . ?
O22 C25 1.4183(19) . ?
N22 C30 1.3333(18) . ?
N22 C29 1.3391(19) . ?
C22 C23 1.5013(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.365(2) . ?
C23 C31 1.4327(18) . ?
C24 C25 1.4975(18) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.382(2) . ?
C27 C31 1.3998(19) . ?
C27 H27 0.9500 . ?
C28 C29 1.407(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.427(2) . ?
O41 C45 1.4194(16) . ?
O41 C46 1.4442(19) . ?
N41 C50 1.3765(17) . ?
N41 C44 1.3816(18) . ?
N41 H92 0.90(2) . ?
C41 O42 1.4508(17) . ?
C41 C42 1.5334(19) . ?
C41 C46 1.550(2) . ?
C41 H41 1.0000 . ?
O42 C45 1.4254(17) . ?
N42 C50 1.3310(18) . ?
N42 C49 1.3417(19) . ?
C42 C43 1.5019(19) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.3614(19) . ?
C43 C51 1.4284(18) . ?
C44 C45 1.5047(18) . ?
C45 H45 1.0000 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.389(2) . ?
C47 C51 1.401(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.395(2) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C51 1.4199(19) . ?
O61 C65 1.4187(16) . ?
O61 C66 1.4463(18) . ?
N61 C70 1.3654(18) . ?
N61 C64 1.3679(18) . ?
N61 H61 0.73(2) . ?
C61 O62 1.4519(19) . ?
C61 C62 1.534(2) . ?
C61 C66 1.5439(19) . ?
C61 H61A 1.0000 . ?
O62 C65 1.4199(17) . ?
N62 C69 1.3374(19) . ?
N62 C70 1.3375(17) . ?
C62 C63 1.5015(19) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.368(2) . ?
C63 C71 1.4343(17) . ?
C64 C65 1.4934(17) . ?
C65 H65 1.0000 . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C67 C68 1.387(2) . ?
C67 C71 1.3958(19) . ?
C67 H67 0.9500 . ?
C68 C69 1.404(2) . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?
C70 C71 1.430(2) . ?
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
{570cea36-6994-4c8b-b621-291524caae51} y y y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346698
