#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/50/2215095.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215095
loop_
_publ_author_name
'Krawiecka, Mariola'
'Wawrzycka-Gorczyca, Irena'
'Galazka, Agnieszka'
'Kossakowski, Jerzy'
'Koziol, Anna E.'
_publ_section_title
;
 10,11-Dihydroxy-4-azatricyclo[5.2.2.0^2,6^]undec-8-ene-3,5-dione
;
_journal_coeditor_code           FL2155
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3878
_journal_page_last               o3878
_journal_paper_doi               10.1107/S1600536807040962
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H11 N O4'
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_name_systematic
;
10,11-Dihydroxy-4-azatricyclo[5.2.2.0^2,6^]undec-8-ene-3,5-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.71(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.524(2)
_cell_length_b                   8.111(2)
_cell_length_c                   11.586(3)
_cell_measurement_reflns_used    76
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      6
_cell_volume                     882.2(4)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1999)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1973
_diffrn_reflns_theta_full        80.20
_diffrn_reflns_theta_max         80.20
_diffrn_reflns_theta_min         5.57
_diffrn_standards_decay_%        0.25
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.232
_refine_ls_extinction_coef       0.092(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0425
_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/[σ²(Fo²)+(0.0746P)²+0.224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1410
_reflns_number_total             1891
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215095
_cod_database_fobs_code          2215095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.32529(18) 0.2170(2) 0.60092(15) 0.0296(4) Uani d . 1
H H1 0.3621 0.2298 0.6847 0.035 Uiso calc R 1
C C2 0.19096(16) 0.3221(2) 0.56282(13) 0.0255(4) Uani d . 1
H H2 0.1184 0.2947 0.6105 0.031 Uiso calc R 1
C C3 0.22198(17) 0.5054(2) 0.56929(15) 0.0282(4) Uani d . 1
O O3 0.28269(15) 0.58212(16) 0.65367(11) 0.0396(4) Uani d . 1
N N4 0.16905(15) 0.57479(17) 0.46334(13) 0.0307(4) Uani d . 1
H H4 0.1667 0.6815 0.4481 0.037 Uiso d R 1
C C5 0.11373(17) 0.4610(2) 0.37877(15) 0.0277(4) Uani d . 1
O O5 0.06147(15) 0.49537(16) 0.27993(11) 0.0391(4) Uani d . 1
C C6 0.13289(17) 0.29072(19) 0.43262(14) 0.0260(4) Uani d . 1
H H6 0.0414 0.2327 0.4235 0.031 Uiso calc R 1
C C7 0.24300(18) 0.1890(2) 0.37810(15) 0.0291(4) Uani d . 1
H H7 0.2162 0.1817 0.2928 0.035 Uiso calc R 1
C C8 0.38806(18) 0.2644(2) 0.41258(17) 0.0348(4) Uani d . 1
H H8 0.4420 0.3021 0.3581 0.042 Uiso calc R 1
C C9 0.43268(18) 0.2726(2) 0.52713(17) 0.0348(4) Uani d . 1
H H9 0.5232 0.3097 0.5595 0.042 Uiso calc R 1
C C10 0.28118(17) 0.0364(2) 0.57016(15) 0.0300(4) Uani d . 1
H H10C 0.3581 -0.0380 0.6045 0.036 Uiso calc R 1
O O10 0.15352(13) -0.00595(16) 0.61250(11) 0.0359(3) Uani d . 1
H H10 0.1659 0.0053 0.6838 0.043 Uiso calc R 1
C C11 0.25367(18) 0.0168(2) 0.43507(15) 0.0302(4) Uani d . 1
H H11C 0.3384 -0.0361 0.4142 0.036 Uiso calc R 1
O O11 0.13623(14) -0.08778(14) 0.39332(11) 0.0356(3) Uani d . 1
H H11 0.0642 -0.0513 0.4142 0.043 Uiso calc R 1
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
C9 C1 C2 106.39(13)
C9 C1 C10 109.62(14)
C2 C1 C10 106.13(13)
C9 C1 H1 111.5
C2 C1 H1 111.5
C10 C1 H1 111.5
C3 C2 C6 104.22(12)
C3 C2 C1 112.56(13)
C6 C2 C1 109.50(13)
C3 C2 H2 110.1
C6 C2 H2 110.1
C1 C2 H2 110.1
O3 C3 N4 124.28(16)
O3 C3 C2 127.05(15)
N4 C3 C2 108.67(14)
C3 N4 C5 113.57(14)
C3 N4 H4 125.2
C5 N4 H4 121.3
O5 C5 N4 124.53(15)
O5 C5 C6 127.31(15)
N4 C5 C6 108.16(14)
C5 C6 C2 104.59(13)
C5 C6 C7 111.13(13)
C2 C6 C7 109.37(13)
C5 C6 H6 110.5
C2 C6 H6 110.5
C7 C6 H6 110.5
C8 C7 C11 105.30(14)
C8 C7 C6 109.28(13)
C11 C7 C6 107.95(13)
C8 C7 H7 111.4
C11 C7 H7 111.4
C6 C7 H7 111.4
C9 C8 C7 114.33(16)
C9 C8 H8 122.8
C7 C8 H8 122.8
C8 C9 C1 114.78(15)
C8 C9 H9 122.6
C1 C9 H9 122.6
O10 C10 C1 111.24(14)
O10 C10 C11 108.25(13)
C1 C10 C11 108.82(13)
O10 C10 H10C 109.5
C1 C10 H10C 109.5
C11 C10 H10C 109.5
C10 O10 H10 109.5
O11 C11 C7 113.81(14)
O11 C11 C10 113.20(14)
C7 C11 C10 109.07(13)
O11 C11 H11C 106.8
C7 C11 H11C 106.8
C10 C11 H11C 106.8
C11 O11 H11 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.508(3)
C1 C2 1.539(2)
C1 C10 1.548(2)
C1 H1 0.9800
C2 C3 1.516(2)
C2 C6 1.538(2)
C2 H2 0.9800
C3 O3 1.219(2)
C3 N4 1.367(2)
N4 C5 1.384(2)
N4 H4 0.8829
C5 O5 1.202(2)
C5 C6 1.514(2)
C6 C7 1.550(2)
C6 H6 0.9800
C7 C8 1.502(2)
C7 C11 1.541(2)
C7 H7 0.9800
C8 C9 1.325(3)
C8 H8 0.9300
C9 H9 0.9300
C10 O10 1.428(2)
C10 C11 1.551(2)
C10 H10C 0.9800
O10 H10 0.8200
C11 O11 1.422(2)
C11 H11C 0.9800
O11 H11 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O11 H11 O10 . 0.82 2.34 2.604(2) 99 yes
N4 H4 O11 1_565 0.88 1.98 2.857(2) 171 yes
O10 H10 O3 2_546 0.82 1.96 2.768(2) 166 yes
O11 H11 O10 3_556 0.82 2.10 2.852(2) 153 yes
C7 H7 O5 2_545 0.98 2.84 3.231(2) 105 no
C8 H8 O5 2_545 0.93 2.96 3.214(2) 98 no
C11 H11C O5 2_545 0.98 2.60 3.289(2) 127 yes
C1 H1 O5 4_666 0.98 2.73 3.279(2) 116 no
C10 H10C O5 4_666 0.98 2.58 3.303(2) 130 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 C2 C3 -54.17(17)
C10 C1 C2 C3 -170.87(14)
C9 C1 C2 C6 61.26(16)
C10 C1 C2 C6 -55.44(17)
C6 C2 C3 O3 -172.16(16)
C1 C2 C3 O3 -53.6(2)
C6 C2 C3 N4 8.35(17)
C1 C2 C3 N4 126.93(15)
O3 C3 N4 C5 175.66(16)
C2 C3 N4 C5 -4.84(19)
C3 N4 C5 O5 179.71(16)
C3 N4 C5 C6 -0.98(19)
O5 C5 C6 C2 -174.55(16)
N4 C5 C6 C2 6.17(17)
O5 C5 C6 C7 67.5(2)
N4 C5 C6 C7 -111.73(15)
C3 C2 C6 C5 -8.53(15)
C1 C2 C6 C5 -129.17(14)
C3 C2 C6 C7 110.57(14)
C1 C2 C6 C7 -10.07(17)
C5 C6 C7 C8 67.34(18)
C2 C6 C7 C8 -47.62(17)
C5 C6 C7 C11 -178.63(13)
C2 C6 C7 C11 66.40(16)
C11 C7 C8 C9 -56.97(19)
C6 C7 C8 C9 58.76(19)
C7 C8 C9 C1 -4.5(2)
C2 C1 C9 C8 -55.88(19)
C10 C1 C9 C8 58.46(19)
C9 C1 C10 O10 -163.83(13)
C2 C1 C10 O10 -49.31(17)
C9 C1 C10 C11 -44.65(17)
C2 C1 C10 C11 69.87(16)
C8 C7 C11 O11 -167.72(14)
C6 C7 C11 O11 75.64(17)
C8 C7 C11 C10 64.83(16)
C6 C7 C11 C10 -51.81(17)
O10 C10 C11 O11 -20.65(18)
C1 C10 C11 O11 -141.68(13)
O10 C10 C11 C7 107.15(15)
C1 C10 C11 C7 -13.88(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072921
