#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229551.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_2229551
loop_
_publ_author_name
'Hashemian, Saeedeh'
'Notash, Behrouz'
_publ_section_title
;
 10-Hydroxy-2-azapentacyclo[10.8.0.0^2,10^.0^4,9^.0^15,20^]icosa-1(12),4(9),5,7,13,15(20),16,18-octaene-3,11-dione
;
_journal_coeditor_code           XU5159
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o680
_journal_paper_doi               10.1107/S1600536811005356
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H11 N1 O3'
_chemical_formula_moiety         'C19 H11 N1 O3'
_chemical_formula_sum            'C19 H11 N O3'
_chemical_formula_weight         301.29
_chemical_name_systematic
;
10-Hydroxy-2-azapentacyclo[10.8.0.0^2,10^.0^4,9^.0^15,20^]icosa-
1(12),4(9),5,7,13,15(20),16,18-octaene-3,11-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.401(13)
_cell_angle_beta                 82.503(13)
_cell_angle_gamma                75.862(12)
_cell_formula_units_Z            2
_cell_length_a                   7.3250(11)
_cell_length_b                   9.7916(16)
_cell_length_c                   10.4532(17)
_cell_measurement_reflns_used    1011
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     683.9(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-RED32 (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_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       -14
_diffrn_reflns_number            7737
_diffrn_reflns_theta_full        29.26
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0436
_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)+(0.0720P)²+0.1037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3161
_reflns_number_total             3627
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5159.cif
_cod_data_source_block           I
_cod_original_cell_volume        683.94(19)
_cod_original_formula_sum        'C19 H11 N1 O3'
_cod_database_code               2229551
_cod_database_fobs_code          2229551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.60706(15) 0.62937(12) 0.49240(11) 0.0298(2) Uani d . 1 . .
C C2 0.69780(16) 0.61664(13) 0.36032(12) 0.0324(2) Uani d . 1 . .
C C3 0.87442(18) 0.53663(16) 0.33404(14) 0.0410(3) Uani d . 1 . .
H H3 0.9488 0.4711 0.4042 0.049 Uiso calc R 1 . .
C C4 0.9358(2) 0.55825(19) 0.19890(16) 0.0494(3) Uani d . 1 . .
H H4 1.0540 0.5065 0.1779 0.059 Uiso calc R 1 . .
C C5 0.8237(2) 0.65604(19) 0.09393(15) 0.0502(3) Uani d . 1 . .
H H5 0.8694 0.6697 0.0042 0.060 Uiso calc R 1 . .
C C6 0.6452(2) 0.73333(16) 0.12066(13) 0.0425(3) Uani d . 1 . .
H H6 0.5690 0.7968 0.0507 0.051 Uiso calc R 1 . .
C C7 0.58481(16) 0.71222(13) 0.25611(12) 0.0332(2) Uani d . 1 . .
C C8 0.40104(16) 0.77784(12) 0.31604(11) 0.0318(2) Uani d . 1 . .
C C9 0.33814(17) 0.94765(13) 0.28511(13) 0.0374(3) Uani d . 1 . .
C C10 0.29102(17) 0.97079(13) 0.41761(13) 0.0358(3) Uani d . 1 . .
C C11 0.19816(19) 1.10289(14) 0.44465(16) 0.0441(3) Uani d . 1 . .
H H11 0.1640 1.1909 0.3742 0.053 Uiso calc R 1 . .
C C12 0.15988(19) 1.09807(16) 0.57670(17) 0.0469(3) Uani d . 1 . .
H H12 0.0981 1.1843 0.5963 0.056 Uiso calc R 1 . .
C C13 0.21185(17) 0.96457(16) 0.68549(15) 0.0413(3) Uani d . 1 . .
C C14 0.1701(2) 0.9614(2) 0.82289(17) 0.0541(4) Uani d . 1 . .
H H14 0.1102 1.0485 0.8415 0.065 Uiso calc R 1 . .
C C15 0.2156(2) 0.8347(2) 0.92698(17) 0.0596(4) Uani d . 1 . .
H H15 0.1890 0.8359 1.0161 0.071 Uiso calc R 1 . .
C C16 0.3028(2) 0.7010(2) 0.90168(15) 0.0545(4) Uani d . 1 . .
H H16 0.3306 0.6140 0.9742 0.065 Uiso calc R 1 . .
C C17 0.34726(19) 0.69747(16) 0.77121(13) 0.0422(3) Uani d . 1 . .
H H17 0.4051 0.6082 0.7558 0.051 Uiso calc R 1 . .
C C18 0.30558(16) 0.82910(14) 0.65996(12) 0.0344(2) Uani d . 1 . .
C C19 0.34334(15) 0.83897(12) 0.52100(12) 0.0310(2) Uani d . 1 . .
O O1 0.67384(13) 0.57343(10) 0.60386(9) 0.0374(2) Uani d . 1 . .
O O2 0.24447(12) 0.73626(10) 0.28658(9) 0.0376(2) Uani d . 1 . .
H H2 0.268(3) 0.630(2) 0.317(2) 0.066(6) Uiso d . 1 . .
O O3 0.32112(19) 1.03639(12) 0.17284(11) 0.0592(3) Uani d . 1 . .
N N1 0.43075(13) 0.72309(10) 0.46469(9) 0.0303(2) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 125.83(10) ?
O1 C1 C2 . . 127.52(10) ?
N1 C1 C2 . . 106.62(9) ?
C3 C2 C7 . . 121.55(11) ?
C3 C2 C1 . . 128.81(11) ?
C7 C2 C1 . . 109.36(10) ?
C2 C3 C4 . . 117.33(12) ?
C2 C3 H3 . . 121.3 ?
C4 C3 H3 . . 121.3 ?
C3 C4 C5 . . 121.23(13) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 121.25(12) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 117.34(13) ?
C5 C6 H6 . . 121.3 ?
C7 C6 H6 . . 121.3 ?
C2 C7 C6 . . 121.28(11) ?
C2 C7 C8 . . 109.15(10) ?
C6 C7 C8 . . 129.57(11) ?
O2 C8 N1 . . 111.82(9) ?
O2 C8 C7 . . 113.83(9) ?
N1 C8 C7 . . 103.29(9) ?
O2 C8 C9 . . 104.10(9) ?
N1 C8 C9 . . 103.13(9) ?
C7 C8 C9 . . 120.25(10) ?
O3 C9 C10 . . 129.58(12) ?
O3 C9 C8 . . 124.77(12) ?
C10 C9 C8 . . 105.45(9) ?
C19 C10 C11 . . 121.77(12) ?
C19 C10 C9 . . 110.43(10) ?
C11 C10 C9 . . 127.75(12) ?
C12 C11 C10 . . 118.08(13) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
C11 C12 C13 . . 121.64(12) ?
C11 C12 H12 . . 119.2 ?
C13 C12 H12 . . 119.2 ?
C14 C13 C12 . . 120.91(13) ?
C14 C13 C18 . . 118.03(14) ?
C12 C13 C18 . . 121.06(12) ?
C15 C14 C13 . . 121.45(14) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 120.45(14) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C17 C16 C15 . . 120.69(16) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 120.21(14) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C19 . . 125.32(11) ?
C17 C18 C13 . . 119.13(12) ?
C19 C18 C13 . . 115.52(12) ?
C10 C19 C18 . . 121.92(11) ?
C10 C19 N1 . . 109.84(10) ?
C18 C19 N1 . . 128.21(10) ?
C8 O2 H2 . . 107.6(12) ?
C1 N1 C19 . . 126.89(9) ?
C1 N1 C8 . . 111.06(9) ?
C19 N1 C8 . . 108.74(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2192(14) ?
C1 N1 . 1.3908(14) ?
C1 C2 . 1.4829(16) ?
C2 C3 . 1.3855(16) ?
C2 C7 . 1.3858(16) ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.393(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3885(17) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.4983(16) ?
C8 O2 . 1.4071(14) ?
C8 N1 . 1.4905(14) ?
C8 C9 . 1.5445(16) ?
C9 O3 . 1.2037(16) ?
C9 C10 . 1.4616(18) ?
C10 C19 . 1.3826(16) ?
C10 C11 . 1.4075(17) ?
C11 C12 . 1.359(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.421(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.420(2) ?
C13 C18 . 1.4307(17) ?
C14 C15 . 1.349(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.404(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3704(18) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.4148(19) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.4177(16) ?
C19 N1 . 1.4278(14) ?
O2 H2 . 0.96(2) ?
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
O2 H2 O1 2_666 0.96(2) 1.85(2) 2.7978(15) 172.2(17) yes
C6 H6 O3 2_675 0.93 2.52 3.1609(18) 126 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 1.8(2) ?
N1 C1 C2 C3 . . . . 179.64(12) ?
O1 C1 C2 C7 . . . . -172.16(12) ?
N1 C1 C2 C7 . . . . 5.70(13) ?
C7 C2 C3 C4 . . . . 1.3(2) ?
C1 C2 C3 C4 . . . . -171.95(12) ?
C2 C3 C4 C5 . . . . -0.3(2) ?
C3 C4 C5 C6 . . . . -1.2(2) ?
C4 C5 C6 C7 . . . . 1.6(2) ?
C3 C2 C7 C6 . . . . -0.90(19) ?
C1 C2 C7 C6 . . . . 173.56(11) ?
C3 C2 C7 C8 . . . . 177.95(11) ?
C1 C2 C7 C8 . . . . -7.60(13) ?
C5 C6 C7 C2 . . . . -0.6(2) ?
C5 C6 C7 C8 . . . . -179.17(13) ?
C2 C7 C8 O2 . . . . -115.06(11) ?
C6 C7 C8 O2 . . . . 63.66(17) ?
C2 C7 C8 N1 . . . . 6.39(12) ?
C6 C7 C8 N1 . . . . -174.89(13) ?
C2 C7 C8 C9 . . . . 120.48(11) ?
C6 C7 C8 C9 . . . . -60.81(18) ?
O2 C8 C9 O3 . . . . -72.49(16) ?
N1 C8 C9 O3 . . . . 170.63(13) ?
C7 C8 C9 O3 . . . . 56.47(18) ?
O2 C8 C9 C10 . . . . 102.75(10) ?
N1 C8 C9 C10 . . . . -14.13(12) ?
C7 C8 C9 C10 . . . . -128.29(11) ?
O3 C9 C10 C19 . . . . -176.69(14) ?
C8 C9 C10 C19 . . . . 8.38(13) ?
O3 C9 C10 C11 . . . . 6.1(2) ?
C8 C9 C10 C11 . . . . -168.84(12) ?
C19 C10 C11 C12 . . . . -0.18(19) ?
C9 C10 C11 C12 . . . . 176.77(12) ?
C10 C11 C12 C13 . . . . 0.3(2) ?
C11 C12 C13 C14 . . . . -179.76(13) ?
C11 C12 C13 C18 . . . . -0.5(2) ?
C12 C13 C14 C15 . . . . 178.73(14) ?
C18 C13 C14 C15 . . . . -0.5(2) ?
C13 C14 C15 C16 . . . . -1.3(2) ?
C14 C15 C16 C17 . . . . 1.6(3) ?
C15 C16 C17 C18 . . . . 0.0(2) ?
C16 C17 C18 C19 . . . . -179.45(13) ?
C16 C17 C18 C13 . . . . -1.7(2) ?
C14 C13 C18 C17 . . . . 2.00(18) ?
C12 C13 C18 C17 . . . . -177.24(12) ?
C14 C13 C18 C19 . . . . 179.92(11) ?
C12 C13 C18 C19 . . . . 0.68(17) ?
C11 C10 C19 C18 . . . . 0.37(18) ?
C9 C10 C19 C18 . . . . -177.05(10) ?
C11 C10 C19 N1 . . . . 178.75(11) ?
C9 C10 C19 N1 . . . . 1.33(14) ?
C17 C18 C19 C10 . . . . 177.17(12) ?
C13 C18 C19 C10 . . . . -0.61(17) ?
C17 C18 C19 N1 . . . . -0.9(2) ?
C13 C18 C19 N1 . . . . -178.66(10) ?
O1 C1 N1 C19 . . . . 40.41(18) ?
C2 C1 N1 C19 . . . . -137.50(11) ?
O1 C1 N1 C8 . . . . 176.42(11) ?
C2 C1 N1 C8 . . . . -1.48(12) ?
C10 C19 N1 C1 . . . . 125.80(12) ?
C18 C19 N1 C1 . . . . -55.95(17) ?
C10 C19 N1 C8 . . . . -11.01(13) ?
C18 C19 N1 C8 . . . . 167.23(11) ?
O2 C8 N1 C1 . . . . 119.96(10) ?
C7 C8 N1 C1 . . . . -2.84(12) ?
C9 C8 N1 C1 . . . . -128.76(10) ?
O2 C8 N1 C19 . . . . -95.95(11) ?
C7 C8 N1 C19 . . . . 141.25(9) ?
C9 C8 N1 C19 . . . . 15.33(11) ?
