#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/17/2221721.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_2221721
loop_
_publ_author_name
'Raza, Abdul Rauf'
'Danish, Muhammad'
'Tahir, M. Nawaz'
'Nisar, Bushra'
'Park, Gyungse'
_publ_section_title
;
 2-Hydroxy-3-nitro-N-phenylbenzamide
;
_journal_coeditor_code           HK2662
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1042
_journal_paper_doi               10.1107/S1600536809013063
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 N2 O4'
_chemical_formula_moiety         'C13 H10 N2 O4'
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_formula_weight         258.23
_chemical_name_systematic
;
2-Hydroxy-3-nitro-N-phenylbenzamide
;
_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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 101.181(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.485(2)
_cell_length_b                   11.465(2)
_cell_length_c                   20.013(4)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.10
_cell_volume                     2360.1(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGx publication routines (Farrugia, 1999) and PLATON  (Spek,
2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.82
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0905
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13479
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0484
_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)+(0.0245P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1880
_reflns_number_total             4190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2662.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221721
_cod_database_fobs_code          2221721
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.1388(2) 0.41856(19) 0.08311(10) 0.0808(10) Uani . . 1.000
O O2 0.4704(2) 0.34896(17) 0.00581(9) 0.0586(8) Uani . . 1.000
O O3 0.5836(3) 0.3805(2) -0.09569(12) 0.0815(11) Uani . . 1.000
O O4 0.4835(3) 0.4655(2) -0.18661(11) 0.1105(13) Uani . . 1.000
O O5 0.79454(13) 0.47437(11) 0.53123(6) 0.0742(10) Uani . . 1.000
O O6 0.44496(13) 0.29222(11) 0.47736(6) 0.0630(9) Uani . . 1.000
O O7 0.2306(2) 0.24638(18) 0.51192(12) 0.0785(10) Uani . . 1.000
O O8 0.1932(2) 0.29716(17) 0.61025(11) 0.0891(11) Uani . . 1.000
N N1 0.3303(3) 0.32209(18) 0.10180(11) 0.0516(10) Uani . . 1.000
N N2 0.4853(4) 0.4287(3) -0.12935(14) 0.0728(14) Uani . . 1.000
N N3 0.6742(2) 0.35952(17) 0.45098(10) 0.0505(10) Uani . . 1.000
N N4 0.2654(3) 0.2946(2) 0.56899(14) 0.0634(11) Uani . . 1.000
C C1 0.2574(3) 0.4220(2) -0.00668(14) 0.0488(11) Uani . . 1.000
C C2 0.3693(3) 0.4033(2) -0.03317(14) 0.0475(11) Uani . . 1.000
C C3 0.3707(4) 0.4438(2) -0.09925(15) 0.0543(13) Uani . . 1.000
C C4 0.2652(4) 0.4996(3) -0.13803(16) 0.0701(16) Uani . . 1.000
C C5 0.1553(4) 0.5164(3) -0.11226(16) 0.0768(16) Uani . . 1.000
C C6 0.1533(4) 0.4784(3) -0.04686(15) 0.0665(14) Uani . . 1.000
C C7 0.2363(4) 0.3878(3) 0.06361(15) 0.0541(14) Uani . . 1.000
C C8 0.3309(3) 0.2730(2) 0.16716(13) 0.0470(11) Uani . . 1.000
C C9 0.2525(3) 0.3112(2) 0.21062(14) 0.0650(14) Uani . . 1.000
C C10 0.2579(4) 0.2549(3) 0.27241(16) 0.0726(16) Uani . . 1.000
C C11 0.3406(4) 0.1640(3) 0.29130(15) 0.0707(16) Uani . . 1.000
C C12 0.4202(3) 0.1278(3) 0.24855(14) 0.0670(14) Uani . . 1.000
C C13 0.41554(13) 0.18195(11) 0.18641(6) 0.0553(11) Uani . . 1.000
C C14 0.5958(3) 0.4037(2) 0.55541(13) 0.0446(11) Uani . . 1.000
C C15 0.4774(3) 0.3463(2) 0.53838(13) 0.0480(13) Uani . . 1.000
C C16 0.3931(3) 0.3471(2) 0.58522(15) 0.0485(11) Uani . . 1.000
C C17 0.4279(4) 0.4007(3) 0.64807(14) 0.0599(14) Uani . . 1.000
C C18 0.5448(3) 0.4560(3) 0.66462(14) 0.0617(13) Uani . . 1.000
C C19 0.6269(3) 0.4582(2) 0.61847(13) 0.0543(11) Uani . . 1.000
C C20 0.6977(3) 0.4154(2) 0.51198(14) 0.0509(13) Uani . . 1.000
C C21 0.7531(3) 0.3568(2) 0.40071(14) 0.0450(11) Uani . . 1.000
C C22 0.8800(3) 0.3951(2) 0.41066(15) 0.0574(14) Uani . . 1.000
C C23 0.9484(3) 0.3838(3) 0.35836(16) 0.0659(14) Uani . . 1.000
C C24 0.8919(4) 0.3353(3) 0.29665(17) 0.0684(14) Uani . . 1.000
C C25 0.7655(4) 0.2979(2) 0.28709(15) 0.0614(14) Uani . . 1.000
C C26 0.6952(3) 0.3085(2) 0.33859(14) 0.0531(12) Uani . . 1.000
H H1N 0.39778 0.30839 0.08451 0.0619 Uiso . . 1.000
H H2O 0.52842 0.34004 -0.01592 0.0704 Uiso . . 1.000
H H4 0.26902 0.52571 -0.18160 0.0839 Uiso . . 1.000
H H5 0.08309 0.55283 -0.13819 0.0923 Uiso . . 1.000
H H6 0.07877 0.49133 -0.02915 0.0798 Uiso . . 1.000
H H9 0.19654 0.37395 0.19859 0.0781 Uiso . . 1.000
H H10 0.20405 0.27973 0.30148 0.0873 Uiso . . 1.000
H H11 0.34297 0.12685 0.33283 0.0848 Uiso . . 1.000
H H12 0.47775 0.06650 0.26144 0.0804 Uiso . . 1.000
H H13 0.46965 0.15678 0.15758 0.0665 Uiso . . 1.000
H H3N 0.60268 0.32091 0.44160 0.0606 Uiso . . 1.000
H H6O 0.36959 0.26924 0.47197 0.0756 Uiso . . 1.000
H H17 0.37186 0.39896 0.67883 0.0716 Uiso . . 1.000
H H18 0.56902 0.49214 0.70679 0.0737 Uiso . . 1.000
H H19 0.70571 0.49738 0.62998 0.0653 Uiso . . 1.000
H H22 0.91923 0.42808 0.45201 0.0686 Uiso . . 1.000
H H23 1.03403 0.40950 0.36497 0.0792 Uiso . . 1.000
H H24 0.93892 0.32807 0.26197 0.0820 Uiso . . 1.000
H H25 0.72657 0.26515 0.24563 0.0736 Uiso . . 1.000
H H26 0.60934 0.28330 0.33162 0.0640 Uiso . . 1.000
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 H2O . . . 109.00 no
C15 O6 H6O . . . 109.00 no
C7 N1 C8 . . . 127.8(3) no
O3 N2 O4 . . . 121.5(4) no
O4 N2 C3 . . . 119.0(3) no
O3 N2 C3 . . . 119.5(3) no
C7 N1 H1N . . . 116.00 no
C8 N1 H1N . . . 116.00 no
C20 N3 C21 . . . 128.1(2) no
O7 N4 O8 . . . 121.0(3) no
O8 N4 C16 . . . 120.4(3) no
O7 N4 C16 . . . 118.7(3) no
C21 N3 H3N . . . 116.00 no
C20 N3 H3N . . . 116.00 no
C2 C1 C7 . . . 126.7(3) no
C2 C1 C6 . . . 118.5(3) no
C6 C1 C7 . . . 114.8(3) no
C1 C2 C3 . . . 118.1(3) no
O2 C2 C3 . . . 123.4(3) no
O2 C2 C1 . . . 118.6(2) no
N2 C3 C4 . . . 117.3(3) no
C2 C3 C4 . . . 122.0(4) no
N2 C3 C2 . . . 120.7(3) no
C3 C4 C5 . . . 119.8(3) no
C4 C5 C6 . . . 118.8(3) no
C1 C6 C5 . . . 122.8(4) no
N1 C7 C1 . . . 116.5(3) no
O1 C7 N1 . . . 123.1(3) no
O1 C7 C1 . . . 120.4(3) no
N1 C8 C13 . . . 116.4(2) no
N1 C8 C9 . . . 123.9(2) no
C9 C8 C13 . . . 119.7(2) no
C8 C9 C10 . . . 119.2(3) no
C9 C10 C11 . . . 121.2(3) no
C10 C11 C12 . . . 119.4(3) no
C11 C12 C13 . . . 120.4(3) no
C8 C13 C12 . . . 120.1(2) no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 121.00 no
C4 C5 H5 . . . 121.00 no
C5 C6 H6 . . . 119.00 no
C1 C6 H6 . . . 119.00 no
C10 C9 H9 . . . 120.00 no
C8 C9 H9 . . . 120.00 no
C9 C10 H10 . . . 119.00 no
C11 C10 H10 . . . 119.00 no
C12 C11 H11 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C8 C13 H13 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
C15 C14 C19 . . . 118.5(3) no
C15 C14 C20 . . . 126.9(2) no
C19 C14 C20 . . . 114.6(3) no
O6 C15 C16 . . . 121.6(3) no
O6 C15 C14 . . . 119.7(2) no
C14 C15 C16 . . . 118.7(2) no
N4 C16 C15 . . . 121.4(3) no
N4 C16 C17 . . . 117.3(3) no
C15 C16 C17 . . . 121.3(3) no
C16 C17 C18 . . . 119.6(3) no
C17 C18 C19 . . . 119.6(3) no
C14 C19 C18 . . . 122.2(3) no
O5 C20 N3 . . . 122.7(3) no
O5 C20 C14 . . . 120.5(2) no
N3 C20 C14 . . . 116.8(2) no
N3 C21 C22 . . . 124.7(2) no
N3 C21 C26 . . . 115.4(3) no
C22 C21 C26 . . . 119.9(3) no
C21 C22 C23 . . . 119.2(3) no
C22 C23 C24 . . . 121.3(3) no
C23 C24 C25 . . . 119.1(3) no
C24 C25 C26 . . . 120.6(3) no
C21 C26 C25 . . . 119.9(3) no
C16 C17 H17 . . . 120.00 no
C18 C17 H17 . . . 120.00 no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C14 C19 H19 . . . 119.00 no
C18 C19 H19 . . . 119.00 no
C21 C22 H22 . . . 120.00 no
C23 C22 H22 . . . 120.00 no
C22 C23 H23 . . . 119.00 no
C24 C23 H23 . . . 119.00 no
C23 C24 H24 . . . 120.00 no
C25 C24 H24 . . . 120.00 no
C24 C25 H25 . . . 120.00 no
C26 C25 H25 . . . 120.00 no
C21 C26 H26 . . . 120.00 no
C25 C26 H26 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . . 1.215(5) no
O2 C2 . . 1.342(3) no
O3 N2 . . 1.246(5) no
O4 N2 . . 1.218(4) no
O2 H2O . . 0.8200 no
O5 C20 . . 1.219(3) no
O6 C15 . . 1.353(3) no
O7 N4 . . 1.258(4) no
O8 N4 . . 1.224(4) no
O6 H6O . . 0.8200 no
N1 C8 . . 1.423(3) no
N1 C7 . . 1.353(4) no
N2 C3 . . 1.455(6) no
N1 H1N . . 0.8600 no
N3 C21 . . 1.421(4) no
N3 C20 . . 1.358(3) no
N4 C16 . . 1.446(4) no
N3 H3N . . 0.8600 no
C1 C2 . . 1.395(4) no
C1 C6 . . 1.384(5) no
C1 C7 . . 1.517(4) no
C2 C3 . . 1.404(4) no
C3 C4 . . 1.379(5) no
C4 C5 . . 1.364(6) no
C5 C6 . . 1.384(4) no
C8 C9 . . 1.379(4) no
C8 C13 . . 1.376(3) no
C9 C10 . . 1.386(4) no
C10 C11 . . 1.362(5) no
C11 C12 . . 1.370(5) no
C12 C13 . . 1.382(3) no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 C19 . . 1.389(4) no
C14 C20 . . 1.508(4) no
C14 C15 . . 1.388(4) no
C15 C16 . . 1.408(4) no
C16 C17 . . 1.384(4) no
C17 C18 . . 1.363(5) no
C18 C19 . . 1.380(4) no
C21 C26 . . 1.389(4) no
C21 C22 . . 1.378(4) no
C22 C23 . . 1.385(4) no
C23 C24 . . 1.379(5) no
C24 C25 . . 1.371(6) no
C25 C26 . . 1.384(5) no
C17 H17 . . 0.9300 no
C18 H18 . . 0.9300 no
C19 H19 . . 0.9300 no
C22 H22 . . 0.9300 no
C23 H23 . . 0.9300 no
C24 H24 . . 0.9300 no
C25 H25 . . 0.9300 no
C26 H26 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C9 2.876(3) . . no
O1 C5 3.332(5) . 3_565 no
O1 C6 3.231(5) . 3_565 no
O2 N2 2.888(3) . . no
O2 O3 2.569(3) . . no
O2 N1 2.653(3) . . no
O2 C3 3.273(4) . 3_665 no
O2 O7 2.920(3) . 4_554 no
O2 C22 3.414(3) . 4_454 no
O2 C2 3.292(3) . 3_665 no
O3 C1 3.283(4) . 3_665 no
O3 O7 2.800(3) . 4_554 no
O3 O2 2.569(3) . . no
O3 C23 3.396(4) . 4_454 no
O3 C7 3.250(5) . 3_665 no
O4 C17 3.330(4) . 1_554 no
O4 C18 3.167(4) . 1_554 no
O5 C22 2.879(3) . . no
O6 O7 2.532(3) . . no
O6 N4 2.872(3) . . no
O6 N3 2.673(3) . . no
O7 O2 2.920(3) . 4_455 no
O7 O3 2.800(3) . 4_455 no
O7 C6 3.329(4) . 2_545 no
O7 C5 3.389(4) . 2_545 no
O7 O6 2.532(3) . . no
O1 H9 2.3300 . . no
O1 H6 2.5500 . 3_565 no
O1 H5 2.7800 . 3_565 no
O1 H6 2.3600 . . no
O1 H11 2.9100 . 2_555 no
O2 H1N 1.9300 . . no
O3 H2O 1.8600 . . no
O4 H17 2.8300 . 1_554 no
O4 H18 2.4900 . 1_554 no
O4 H4 2.3700 . . no
O5 H23 2.8100 . 3_766 no
O5 H22 2.3000 . . no
O5 H19 2.3600 . . no
O6 H3N 1.9500 . . no
O7 H2O 2.3100 . 4_455 no
O7 H6O 1.8100 . . no
O8 H13 2.7400 . 4_455 no
O8 H17 2.4000 . . no
O8 H25 2.7600 . 4_455 no
N1 C20 3.407(3) . 4_454 no
N1 O2 2.653(3) . . no
N2 O2 2.888(3) . . no
N2 C24 3.428(5) . 4_454 no
N3 C17 3.437(4) . 3_666 no
N3 C1 3.407(3) . 4_555 no
N3 O6 2.673(3) . . no
N4 O6 2.872(3) . . no
N4 C5 3.367(4) . 2_545 no
N2 H2O 2.4500 . . no
N4 H6O 2.4200 . . no
C1 N3 3.407(3) . 4_454 no
C1 O3 3.283(4) . 3_665 no
C2 C2 3.575(4) . 3_665 no
C2 C21 3.392(4) . 4_454 no
C2 O2 3.292(3) . 3_665 no
C3 C26 3.523(4) . 4_454 no
C3 O2 3.273(4) . 3_665 no
C5 O7 3.389(4) . 2_555 no
C5 N4 3.367(4) . 2_555 no
C5 O1 3.332(5) . 3_565 no
C6 O7 3.329(4) . 2_555 no
C6 O1 3.231(5) . 3_565 no
C7 O3 3.250(5) . 3_665 no
C8 C19 3.427(4) . 4_454 no
C9 O1 2.876(3) . . no
C13 C19 3.463(3) . 4_454 no
C14 C15 3.431(3) . 3_666 no
C14 C14 3.479(4) . 3_666 no
C15 C20 3.337(4) . 3_666 no
C15 C14 3.431(3) . 3_666 no
C16 C20 3.374(4) . 3_666 no
C17 C21 3.401(4) . 3_666 no
C17 O4 3.330(4) . 1_556 no
C17 N3 3.437(4) . 3_666 no
C18 O4 3.167(4) . 1_556 no
C19 C8 3.427(4) . 4_555 no
C19 C13 3.463(3) . 4_555 no
C20 C16 3.374(4) . 3_666 no
C20 C15 3.337(4) . 3_666 no
C20 N1 3.407(3) . 4_555 no
C21 C17 3.401(4) . 3_666 no
C21 C2 3.392(4) . 4_555 no
C22 O5 2.879(3) . . no
C22 O2 3.414(3) . 4_555 no
C23 O3 3.396(4) . 4_555 no
C24 N2 3.428(5) . 4_555 no
C26 C3 3.523(4) . 4_555 no
C2 H1N 2.5600 . . no
C5 H12 2.9900 . 4_454 no
C7 H9 2.8200 . . no
C11 H26 3.1000 . . no
C12 H26 2.9300 . . no
C13 H19 3.0600 . 4_454 no
C15 H3N 2.5600 . . no
C20 H22 2.8200 . . no
C24 H4 3.0300 . 3_665 no
C25 H4 2.9000 . 3_665 no
H1N O2 1.9300 . . no
H1N H13 2.3000 . . no
H1N C2 2.5600 . . no
H2O O3 1.8600 . . no
H2O O7 2.3100 . 4_554 no
H2O N2 2.4500 . . no
H3N H26 2.2600 . . no
H3N C15 2.5600 . . no
H3N O6 1.9500 . . no
H4 C25 2.9000 . 3_665 no
H4 O4 2.3700 . . no
H4 C24 3.0300 . 3_665 no
H5 H12 2.5000 . 4_454 no
H5 O1 2.7800 . 3_565 no
H6 H6 2.2100 . 3_565 no
H6 O1 2.5500 . 3_565 no
H6 O1 2.3600 . . no
H6O O7 1.8100 . . no
H6O N4 2.4200 . . no
H9 C7 2.8200 . . no
H9 O1 2.3300 . . no
H11 O1 2.9100 . 2_545 no
H12 C5 2.9900 . 4_555 no
H12 H5 2.5000 . 4_555 no
H13 H1N 2.3000 . . no
H13 O8 2.7400 . 4_554 no
H17 O4 2.8300 . 1_556 no
H17 O8 2.4000 . . no
H18 O4 2.4900 . 1_556 no
H19 O5 2.3600 . . no
H19 C13 3.0600 . 4_555 no
H22 O5 2.3000 . . no
H22 C20 2.8200 . . no
H23 O5 2.8100 . 3_766 no
H25 O8 2.7600 . 4_554 no
H26 C11 3.1000 . . no
H26 C12 2.9300 . . no
H26 H3N 2.2600 . . no
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
N1 H1N O2 . 0.86 1.93 2.653(3) 140 yes
O2 H2O O3 . 0.82 1.86 2.569(3) 144 yes
O2 H2O O7 4_554 0.82 2.31 2.920(3) 132 yes
N3 H3N O6 . 0.86 1.95 2.673(3) 140 yes
O6 H6O O7 . 0.82 1.81 2.532(3) 146 yes
C6 H6 O1 3_565 0.93 2.55 3.231(5) 131 yes
C18 H18 O4 1_556 0.93 2.49 3.167(4) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C7 O1 . . . . 3.6(5) no
C8 N1 C7 C1 . . . . -176.0(2) no
C7 N1 C8 C9 . . . . -19.2(4) no
C7 N1 C8 C13 . . . . 160.6(3) no
O3 N2 C3 C2 . . . . -0.8(4) no
O3 N2 C3 C4 . . . . 178.8(3) no
O4 N2 C3 C2 . . . . -179.6(3) no
O4 N2 C3 C4 . . . . 0.1(4) no
C20 N3 C21 C26 . . . . -169.9(2) no
C21 N3 C20 O5 . . . . 1.0(4) no
C21 N3 C20 C14 . . . . 179.7(2) no
C20 N3 C21 C22 . . . . 11.9(4) no
O8 N4 C16 C15 . . . . -179.4(2) no
O8 N4 C16 C17 . . . . -0.9(4) no
O7 N4 C16 C17 . . . . 179.2(3) no
O7 N4 C16 C15 . . . . 0.8(4) no
C7 C1 C2 C3 . . . . -178.7(3) no
C6 C1 C7 N1 . . . . 173.5(3) no
C6 C1 C2 C3 . . . . 0.6(4) no
C2 C1 C6 C5 . . . . 0.4(5) no
C7 C1 C6 C5 . . . . 179.7(3) no
C2 C1 C7 O1 . . . . 173.1(3) no
C2 C1 C7 N1 . . . . -7.3(4) no
C6 C1 C7 O1 . . . . -6.2(4) no
C6 C1 C2 O2 . . . . 179.8(3) no
C7 C1 C2 O2 . . . . 0.5(4) no
O2 C2 C3 N2 . . . . -0.2(4) no
O2 C2 C3 C4 . . . . -179.9(3) no
C1 C2 C3 N2 . . . . 179.0(3) no
C1 C2 C3 C4 . . . . -0.7(4) no
N2 C3 C4 C5 . . . . -179.8(3) no
C2 C3 C4 C5 . . . . -0.2(5) no
C3 C4 C5 C6 . . . . 1.1(5) no
C4 C5 C6 C1 . . . . -1.2(5) no
C13 C8 C9 C10 . . . . -1.7(4) no
N1 C8 C13 C12 . . . . -178.7(2) no
C9 C8 C13 C12 . . . . 1.1(4) no
N1 C8 C9 C10 . . . . 178.0(3) no
C8 C9 C10 C11 . . . . 1.1(5) no
C9 C10 C11 C12 . . . . 0.2(5) no
C10 C11 C12 C13 . . . . -0.8(5) no
C11 C12 C13 C8 . . . . 0.2(4) no
C19 C14 C15 O6 . . . . -179.8(2) no
C19 C14 C15 C16 . . . . 0.9(4) no
C20 C14 C15 O6 . . . . 0.8(4) no
C20 C14 C15 C16 . . . . -178.5(2) no
C15 C14 C19 C18 . . . . 0.7(4) no
C20 C14 C19 C18 . . . . -179.9(3) no
C15 C14 C20 O5 . . . . 175.5(2) no
C15 C14 C20 N3 . . . . -3.3(4) no
C19 C14 C20 O5 . . . . -3.9(3) no
C19 C14 C20 N3 . . . . 177.4(2) no
O6 C15 C16 N4 . . . . -2.8(4) no
O6 C15 C16 C17 . . . . 178.8(2) no
C14 C15 C16 N4 . . . . 176.5(2) no
C14 C15 C16 C17 . . . . -1.9(4) no
N4 C16 C17 C18 . . . . -177.1(3) no
C15 C16 C17 C18 . . . . 1.4(5) no
C16 C17 C18 C19 . . . . 0.2(5) no
C17 C18 C19 C14 . . . . -1.2(5) no
N3 C21 C22 C23 . . . . 177.6(3) no
C26 C21 C22 C23 . . . . -0.5(4) no
N3 C21 C26 C25 . . . . -177.6(2) no
C22 C21 C26 C25 . . . . 0.6(4) no
C21 C22 C23 C24 . . . . 0.1(5) no
C22 C23 C24 C25 . . . . 0.1(5) no
C23 C24 C25 C26 . . . . 0.0(5) no
C24 C25 C26 C21 . . . . -0.4(4) no
