#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224727.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_2224727
loop_
_publ_author_name
'Khaledi, Hamid'
'Alhadi, Abeer A.'
'Mohd Ali, Hapipah'
'Robinson, Ward T.'
'Abdulla, Mahmood A.'
_publ_section_title
;3,4,5-Trihydroxy-N'-(1H-indol-2-ylmethylidene)benzohydrazide--1H-indole-2-carbaldehyde
 azine--methanol (2/1/2)
;
_journal_coeditor_code           OM2302
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o105
_journal_page_last               o106
_journal_paper_doi               10.1107/S1600536809052465
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C16 H13 N3 O4, C18 H14 N4, 2C H4 O'
_chemical_formula_moiety         '2(C16 H13 N3 O4), C18 H14 N4, 2(C H4 O)'
_chemical_formula_sum            'C52 H48 N10 O10'
_chemical_formula_weight         973.00
_chemical_name_systematic
;
3,4,5-Trihydroxy-N'-(1H-indol-2-ylmethylidene)benzohydrazide--
1H-indole-2-carbaldehyde azine--methanol (2/1/2)
;
_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                95.918(3)
_cell_angle_beta                 95.166(4)
_cell_angle_gamma                101.451(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4642(15)
_cell_length_b                   12.791(2)
_cell_length_c                   25.079(5)
_cell_measurement_reflns_used    754
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.74
_cell_measurement_theta_min      2.47
_cell_volume                     2319.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'X-SEED (Barbour, 2001) and Mercury (Macrae et al.,  2008)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.1358
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10985
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         7939
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                4029
_reflns_number_total             7939
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om2302.cif
_cod_data_source_block           I
_cod_original_cell_volume        2319.3(8)
_cod_database_code               2224727
_cod_database_fobs_code          2224727
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
O O10 0.7343(4) 0.2306(2) 0.60742(10) 0.0276(7) Uani d . 1 . .
O O13 0.7280(4) 0.0510(2) 0.41802(11) 0.0333(8) Uani d D 1 . .
H H13O 0.749(6) 0.003(3) 0.3953(14) 0.050 Uiso d D 1 . .
O O14 0.7874(4) -0.1457(2) 0.42855(11) 0.0280(7) Uani d D 1 . .
H H14O 0.823(6) -0.201(2) 0.4370(17) 0.042 Uiso d D 1 . .
O O15 0.8285(4) -0.2137(2) 0.52914(10) 0.0259(7) Uani d D 1 . .
H H15O 0.846(6) -0.225(3) 0.5616(6) 0.039 Uiso d D 1 . .
N N1 0.5730(5) 0.2917(3) 0.78752(12) 0.0211(8) Uani d D 1 . .
H H1N 0.571(5) 0.321(3) 0.7570(8) 0.025 Uiso d D 1 . .
N N2 0.6671(5) 0.1652(2) 0.70038(13) 0.0242(8) Uani d . 1 . .
N N3 0.6927(5) 0.0943(3) 0.65781(13) 0.0260(8) Uani d D 1 . .
H H3N 0.668(5) 0.0250(10) 0.6599(15) 0.031 Uiso d D 1 . .
C C1 0.6341(5) 0.1973(3) 0.79275(15) 0.0203(9) Uani d . 1 . .
C C2 0.6431(5) 0.1802(3) 0.84590(15) 0.0263(10) Uani d . 1 . .
H H2 0.6815 0.1215 0.8604 0.032 Uiso calc R 1 . .
C C3 0.5848(5) 0.2656(3) 0.87524(15) 0.0232(10) Uani d . 1 . .
C C4 0.5625(6) 0.2922(3) 0.92965(16) 0.0290(11) Uani d . 1 . .
H H4 0.5937 0.2486 0.9560 0.035 Uiso calc R 1 . .
C C5 0.4951(6) 0.3823(3) 0.94423(16) 0.0317(11) Uani d . 1 . .
H H5 0.4791 0.4007 0.9809 0.038 Uiso calc R 1 . .
C C6 0.4495(6) 0.4473(3) 0.90547(17) 0.0325(11) Uani d . 1 . .
H H6 0.4025 0.5088 0.9167 0.039 Uiso calc R 1 . .
C C7 0.4705(5) 0.4250(3) 0.85215(16) 0.0263(10) Uani d . 1 . .
H H7 0.4386 0.4696 0.8263 0.032 Uiso calc R 1 . .
C C8 0.5402(5) 0.3347(3) 0.83727(15) 0.0222(10) Uani d . 1 . .
C C9 0.6730(5) 0.1316(3) 0.74681(16) 0.0258(10) Uani d . 1 . .
H H9 0.7028 0.0639 0.7509 0.031 Uiso calc R 1 . .
C C10 0.7225(6) 0.1329(3) 0.61037(16) 0.0235(10) Uani d . 1 . .
C C11 0.7412(5) 0.0573(3) 0.56412(15) 0.0199(9) Uani d . 1 . .
C C12 0.7246(5) 0.0893(3) 0.51285(15) 0.0219(10) Uani d . 1 . .
H H12 0.7020 0.1585 0.5083 0.026 Uiso calc R 1 . .
C C13 0.7412(5) 0.0194(3) 0.46881(15) 0.0207(9) Uani d . 1 . .
C C14 0.7731(5) -0.0820(3) 0.47460(15) 0.0203(9) Uani d . 1 . .
C C15 0.7928(5) -0.1131(3) 0.52580(15) 0.0191(9) Uani d . 1 . .
C C16 0.7771(5) -0.0445(3) 0.57041(15) 0.0223(10) Uani d . 1 . .
H H16 0.7907 -0.0661 0.6054 0.027 Uiso calc R 1 . .
O O26 0.8842(4) 0.7516(2) 0.62971(10) 0.0246(7) Uani d . 1 . .
O O29 1.3673(4) 0.6412(2) 0.51863(11) 0.0276(7) Uani d D 1 . .
H H29O 1.430(5) 0.601(3) 0.5035(15) 0.041 Uiso d D 1 . .
O O30 1.3089(4) 0.4224(2) 0.51396(10) 0.0225(7) Uani d D 1 . .
H H30O 1.254(5) 0.3578(13) 0.5053(15) 0.034 Uiso d D 1 . .
O O31 1.0303(4) 0.3140(2) 0.56466(11) 0.0279(7) Uani d D 1 . .
H H31O 0.938(4) 0.293(3) 0.5802(15) 0.042 Uiso d D 1 . .
N N4 0.5999(5) 0.7939(3) 0.79555(12) 0.0230(8) Uani d D 1 . .
H H4N 0.609(5) 0.820(3) 0.7648(8) 0.028 Uiso d D 1 . .
N N5 0.7553(5) 0.6765(2) 0.71588(12) 0.0243(8) Uani d . 1 . .
N N6 0.8261(5) 0.6142(3) 0.67896(13) 0.0240(8) Uani d D 1 . .
H H6N 0.818(5) 0.5464(12) 0.6837(15) 0.029 Uiso d D 1 . .
C C17 0.6739(5) 0.7044(3) 0.80452(15) 0.0233(10) Uani d . 1 . .
C C18 0.6735(5) 0.6888(3) 0.85733(15) 0.0241(10) Uani d . 1 . .
H H18 0.7163 0.6331 0.8736 0.029 Uiso calc R 1 . .
C C19 0.5975(5) 0.7705(3) 0.88380(15) 0.0232(10) Uani d . 1 . .
C C20 0.5626(6) 0.7976(3) 0.93695(16) 0.0284(11) Uani d . 1 . .
H H20 0.5955 0.7576 0.9648 0.034 Uiso calc R 1 . .
C C21 0.4798(6) 0.8830(3) 0.94795(16) 0.0312(11) Uani d . 1 . .
H H21 0.4562 0.9024 0.9838 0.037 Uiso calc R 1 . .
C C22 0.4298(6) 0.9418(3) 0.90718(17) 0.0315(11) Uani d . 1 . .
H H22 0.3710 0.9996 0.9160 0.038 Uiso calc R 1 . .
C C23 0.4630(5) 0.9184(3) 0.85492(16) 0.0250(10) Uani d . 1 . .
H H23 0.4264 0.9583 0.8274 0.030 Uiso calc R 1 . .
C C24 0.5516(5) 0.8349(3) 0.84352(15) 0.0209(9) Uani d . 1 . .
C C25 0.7390(5) 0.6424(3) 0.76214(15) 0.0233(10) Uani d . 1 . .
H H25 0.7701 0.5758 0.7683 0.028 Uiso calc R 1 . .
C C26 0.8945(5) 0.6580(3) 0.63666(15) 0.0209(9) Uani d . 1 . .
C C27 0.9906(5) 0.5921(3) 0.60161(14) 0.0201(9) Uani d . 1 . .
C C28 1.1271(5) 0.6445(3) 0.57419(14) 0.0198(9) Uani d . 1 . .
H H28 1.1494 0.7206 0.5756 0.024 Uiso calc R 1 . .
C C29 1.2315(5) 0.5871(3) 0.54470(15) 0.0209(9) Uani d . 1 . .
C C30 1.1997(5) 0.4760(3) 0.54255(14) 0.0183(9) Uani d . 1 . .
C C31 1.0592(5) 0.4240(3) 0.56948(14) 0.0185(9) Uani d . 1 . .
C C32 0.9561(5) 0.4800(3) 0.59929(14) 0.0188(9) Uani d . 1 . .
H H32 0.8627 0.4434 0.6181 0.023 Uiso calc R 1 . .
N N7 -0.1199(5) 0.3424(3) 1.11800(14) 0.0329(9) Uani d D 1 . .
H H7N -0.160(5) 0.2730(11) 1.1082(15) 0.039 Uiso d D 1 . .
N N8 -0.0309(5) 0.2620(3) 1.01631(15) 0.0412(10) Uani d . 1 . .
N N9 0.0213(5) 0.2391(3) 0.96486(15) 0.0413(10) Uani d . 1 . .
N N10 0.0984(5) 0.1700(3) 0.86232(16) 0.0390(10) Uani d D 1 . .
H H10N 0.140(6) 0.2386(12) 0.8734(17) 0.047 Uiso d D 1 . .
C C33 -0.0304(6) 0.4065(4) 1.08362(17) 0.0338(11) Uani d . 1 . .
C C34 0.0234(6) 0.5092(4) 1.10970(17) 0.0338(11) Uani d . 1 . .
H H34 0.0883 0.5694 1.0952 0.041 Uiso calc R 1 . .
C C35 -0.0343(6) 0.5100(4) 1.16199(17) 0.0318(11) Uani d . 1 . .
C C36 -0.0175(6) 0.5877(4) 1.20641(18) 0.0365(12) Uani d . 1 . .
H H36 0.0427 0.6598 1.2047 0.044 Uiso calc R 1 . .
C C37 -0.0892(6) 0.5589(4) 1.25316(18) 0.0364(12) Uani d . 1 . .
H H37 -0.0783 0.6116 1.2835 0.044 Uiso calc R 1 . .
C C38 -0.1782(6) 0.4520(4) 1.25592(18) 0.0355(12) Uani d . 1 . .
H H38 -0.2267 0.4337 1.2883 0.043 Uiso calc R 1 . .
C C39 -0.1965(6) 0.3734(4) 1.21283(17) 0.0342(11) Uani d . 1 . .
H H39 -0.2565 0.3014 1.2151 0.041 Uiso calc R 1 . .
C C40 -0.1247(6) 0.4023(3) 1.16585(17) 0.0299(11) Uani d . 1 . .
C C41 0.0086(6) 0.3637(4) 1.03193(17) 0.0351(12) Uani d . 1 . .
H H41 0.0648 0.4113 1.0087 0.042 Uiso calc R 1 . .
C C42 -0.0074(6) 0.1373(4) 0.94922(19) 0.0404(12) Uani d . 1 . .
H H42 -0.0528 0.0874 0.9729 0.048 Uiso calc R 1 . .
C C43 0.0283(6) 0.0996(4) 0.8971(2) 0.0404(12) Uani d . 1 . .
C C44 -0.0064(6) -0.0023(4) 0.8699(2) 0.0450(13) Uani d . 1 . .
H H44 -0.0547 -0.0667 0.8842 0.054 Uiso calc R 1 . .
C C45 0.0423(6) 0.0051(4) 0.8166(2) 0.0388(12) Uani d . 1 . .
C C46 0.0367(6) -0.0702(4) 0.7703(2) 0.0505(15) Uani d . 1 . .
H H46 -0.0038 -0.1450 0.7716 0.061 Uiso calc R 1 . .
C C47 0.0905(7) -0.0332(5) 0.7238(2) 0.0575(16) Uani d . 1 . .
H H47 0.0874 -0.0831 0.6927 0.069 Uiso calc R 1 . .
C C48 0.1500(6) 0.0768(4) 0.7210(2) 0.0519(15) Uani d . 1 . .
H H48 0.1842 0.1002 0.6879 0.062 Uiso calc R 1 . .
C C49 0.1598(6) 0.1511(4) 0.76502(19) 0.0454(13) Uani d . 1 . .
H H49 0.2018 0.2256 0.7631 0.055 Uiso calc R 1 . .
C C50 0.1067(6) 0.1146(4) 0.81268(19) 0.0379(12) Uani d . 1 . .
O O51 0.3727(4) 0.6124(2) 0.31454(11) 0.0291(7) Uani d D 1 . .
H H51O 0.348(6) 0.6718(18) 0.3249(16) 0.044 Uiso d D 1 . .
C C51 0.5272(6) 0.6038(4) 0.35040(18) 0.0448(13) Uani d . 1 . .
H H51A 0.6326 0.6607 0.3464 0.067 Uiso calc R 1 . .
H H51B 0.5580 0.5335 0.3418 0.067 Uiso calc R 1 . .
H H51C 0.4971 0.6114 0.3876 0.067 Uiso calc R 1 . .
O O52 0.3718(4) 0.1291(2) 0.31264(11) 0.0270(7) Uani d D 1 . .
H H52O 0.303(5) 0.173(3) 0.3177(17) 0.040 Uiso d D 1 . .
C C52 0.5328(6) 0.1969(3) 0.34338(17) 0.0348(11) Uani d . 1 . .
H H52A 0.5520 0.2685 0.3315 0.052 Uiso calc R 1 . .
H H52B 0.6404 0.1656 0.3378 0.052 Uiso calc R 1 . .
H H52C 0.5157 0.2028 0.3818 0.052 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 0.0033 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'
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
C13 O13 H13O . . 110(3) ?
C14 O14 H14O . . 109(3) ?
C15 O15 H15O . . 111(3) ?
C8 N1 C1 . . 109.0(3) ?
C8 N1 H1N . . 128(2) ?
C1 N1 H1N . . 123(2) ?
C9 N2 N3 . . 116.0(3) ?
C10 N3 N2 . . 117.8(3) ?
C10 N3 H3N . . 121(3) ?
N2 N3 H3N . . 120(3) ?
C2 C1 N1 . . 109.0(3) ?
C2 C1 C9 . . 129.2(4) ?
N1 C1 C9 . . 121.8(4) ?
C1 C2 C3 . . 107.8(4) ?
C1 C2 H2 . . 126.1 ?
C3 C2 H2 . . 126.1 ?
C4 C3 C2 . . 134.7(4) ?
C4 C3 C8 . . 118.5(4) ?
C2 C3 C8 . . 106.8(3) ?
C5 C4 C3 . . 119.1(4) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 120.7(4) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 122.2(4) ?
C7 C6 H6 . . 118.9 ?
C5 C6 H6 . . 118.9 ?
C6 C7 C8 . . 117.3(4) ?
C6 C7 H7 . . 121.3 ?
C8 C7 H7 . . 121.3 ?
N1 C8 C7 . . 130.5(4) ?
N1 C8 C3 . . 107.4(3) ?
C7 C8 C3 . . 122.1(4) ?
N2 C9 C1 . . 119.6(4) ?
N2 C9 H9 . . 120.2 ?
C1 C9 H9 . . 120.2 ?
O10 C10 N3 . . 119.5(3) ?
O10 C10 C11 . . 122.3(4) ?
N3 C10 C11 . . 118.2(4) ?
C12 C11 C16 . . 119.8(3) ?
C12 C11 C10 . . 118.2(4) ?
C16 C11 C10 . . 121.9(4) ?
C13 C12 C11 . . 119.2(4) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
O13 C13 C12 . . 119.7(3) ?
O13 C13 C14 . . 119.0(3) ?
C12 C13 C14 . . 121.3(4) ?
O14 C14 C13 . . 117.1(3) ?
O14 C14 C15 . . 123.5(4) ?
C13 C14 C15 . . 119.4(3) ?
O15 C15 C16 . . 122.9(4) ?
O15 C15 C14 . . 116.8(3) ?
C16 C15 C14 . . 120.3(4) ?
C15 C16 C11 . . 119.9(4) ?
C15 C16 H16 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
C29 O29 H29O . . 113(3) ?
C30 O30 H30O . . 109(3) ?
C31 O31 H31O . . 107(3) ?
C24 N4 C17 . . 108.0(3) ?
C24 N4 H4N . . 131(3) ?
C17 N4 H4N . . 120(3) ?
C25 N5 N6 . . 116.1(3) ?
C26 N6 N5 . . 118.8(3) ?
C26 N6 H6N . . 124(3) ?
N5 N6 H6N . . 117(3) ?
C18 C17 N4 . . 109.7(3) ?
C18 C17 C25 . . 128.0(4) ?
N4 C17 C25 . . 122.2(4) ?
C17 C18 C19 . . 107.8(4) ?
C17 C18 H18 . . 126.1 ?
C19 C18 H18 . . 126.1 ?
C20 C19 C18 . . 134.9(4) ?
C20 C19 C24 . . 118.8(4) ?
C18 C19 C24 . . 106.3(3) ?
C21 C20 C19 . . 118.8(4) ?
C21 C20 H20 . . 120.6 ?
C19 C20 H20 . . 120.6 ?
C20 C21 C22 . . 121.0(4) ?
C20 C21 H21 . . 119.5 ?
C22 C21 H21 . . 119.5 ?
C23 C22 C21 . . 122.0(4) ?
C23 C22 H22 . . 119.0 ?
C21 C22 H22 . . 119.0 ?
C22 C23 C24 . . 117.7(4) ?
C22 C23 H23 . . 121.2 ?
C24 C23 H23 . . 121.2 ?
N4 C24 C23 . . 130.2(4) ?
N4 C24 C19 . . 108.1(3) ?
C23 C24 C19 . . 121.6(4) ?
N5 C25 C17 . . 120.5(4) ?
N5 C25 H25 . . 119.8 ?
C17 C25 H25 . . 119.8 ?
O26 C26 N6 . . 120.4(3) ?
O26 C26 C27 . . 122.7(4) ?
N6 C26 C27 . . 116.9(4) ?
C28 C27 C32 . . 120.0(3) ?
C28 C27 C26 . . 118.3(4) ?
C32 C27 C26 . . 121.5(3) ?
C27 C28 C29 . . 120.5(4) ?
C27 C28 H28 . . 119.7 ?
C29 C28 H28 . . 119.7 ?
O29 C29 C28 . . 119.2(3) ?
O29 C29 C30 . . 120.8(3) ?
C28 C29 C30 . . 120.0(4) ?
O30 C30 C29 . . 118.2(3) ?
O30 C30 C31 . . 122.9(3) ?
C29 C30 C31 . . 118.9(3) ?
C32 C31 O31 . . 121.9(3) ?
C32 C31 C30 . . 121.7(4) ?
O31 C31 C30 . . 116.4(3) ?
C31 C32 C27 . . 118.9(3) ?
C31 C32 H32 . . 120.5 ?
C27 C32 H32 . . 120.5 ?
C40 N7 C33 . . 109.8(4) ?
C40 N7 H7N . . 130(3) ?
C33 N7 H7N . . 120(3) ?
C41 N8 N9 . . 111.2(4) ?
C42 N9 N8 . . 112.7(4) ?
C43 N10 C50 . . 110.2(4) ?
C43 N10 H10N . . 121(3) ?
C50 N10 H10N . . 128(3) ?
C34 C33 N7 . . 108.4(4) ?
C34 C33 C41 . . 129.2(4) ?
N7 C33 C41 . . 122.2(4) ?
C33 C34 C35 . . 108.3(4) ?
C33 C34 H34 . . 125.9 ?
C35 C34 H34 . . 125.9 ?
C36 C35 C34 . . 135.0(4) ?
C36 C35 C40 . . 119.0(4) ?
C34 C35 C40 . . 106.0(4) ?
C37 C36 C35 . . 119.5(4) ?
C37 C36 H36 . . 120.3 ?
C35 C36 H36 . . 120.3 ?
C36 C37 C38 . . 120.4(4) ?
C36 C37 H37 . . 119.8 ?
C38 C37 H37 . . 119.8 ?
C39 C38 C37 . . 121.5(4) ?
C39 C38 H38 . . 119.3 ?
C37 C38 H38 . . 119.3 ?
C38 C39 C40 . . 118.1(4) ?
C38 C39 H39 . . 120.9 ?
C40 C39 H39 . . 120.9 ?
N7 C40 C39 . . 131.0(4) ?
N7 C40 C35 . . 107.5(4) ?
C39 C40 C35 . . 121.5(4) ?
N8 C41 C33 . . 121.3(4) ?
N8 C41 H41 . . 119.3 ?
C33 C41 H41 . . 119.3 ?
N9 C42 C43 . . 120.3(5) ?
N9 C42 H42 . . 119.8 ?
C43 C42 H42 . . 119.8 ?
C44 C43 N10 . . 107.8(4) ?
C44 C43 C42 . . 130.9(5) ?
N10 C43 C42 . . 121.2(4) ?
C43 C44 C45 . . 108.2(4) ?
C43 C44 H44 . . 125.9 ?
C45 C44 H44 . . 125.9 ?
C50 C45 C46 . . 118.1(5) ?
C50 C45 C44 . . 107.0(4) ?
C46 C45 C44 . . 134.9(5) ?
C47 C46 C45 . . 119.0(5) ?
C47 C46 H46 . . 120.5 ?
C45 C46 H46 . . 120.5 ?
C46 C47 C48 . . 121.2(5) ?
C46 C47 H47 . . 119.4 ?
C48 C47 H47 . . 119.4 ?
C49 C48 C47 . . 121.3(5) ?
C49 C48 H48 . . 119.4 ?
C47 C48 H48 . . 119.4 ?
C48 C49 C50 . . 118.1(5) ?
C48 C49 H49 . . 121.0 ?
C50 C49 H49 . . 121.0 ?
N10 C50 C49 . . 130.9(4) ?
N10 C50 C45 . . 106.9(4) ?
C49 C50 C45 . . 122.2(4) ?
C51 O51 H51O . . 106(3) ?
O51 C51 H51A . . 109.5 ?
O51 C51 H51B . . 109.5 ?
H51A C51 H51B . . 109.5 ?
O51 C51 H51C . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
C52 O52 H52O . . 95(3) ?
O52 C52 H52A . . 109.5 ?
O52 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
O52 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
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
O10 C10 . 1.246(4) ?
O13 C13 . 1.376(4) ?
O13 H13O . 0.844(10) ?
O14 C14 . 1.368(4) ?
O14 H14O . 0.843(10) ?
O15 C15 . 1.374(4) ?
O15 H15O . 0.845(10) ?
N1 C8 . 1.373(5) ?
N1 C1 . 1.387(5) ?
N1 H1N . 0.884(10) ?
N2 C9 . 1.282(5) ?
N2 N3 . 1.380(4) ?
N3 C10 . 1.354(5) ?
N3 H3N . 0.877(10) ?
C1 C2 . 1.371(5) ?
C1 C9 . 1.440(5) ?
C2 C3 . 1.415(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.405(5) ?
C3 C8 . 1.426(5) ?
C4 C5 . 1.375(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.404(6) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.368(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.389(5) ?
C7 H7 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C11 . 1.467(5) ?
C11 C12 . 1.392(5) ?
C11 C16 . 1.401(5) ?
C12 C13 . 1.378(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(5) ?
C14 C15 . 1.387(5) ?
C15 C16 . 1.377(5) ?
C16 H16 . 0.9500 ?
O26 C26 . 1.243(4) ?
O29 C29 . 1.367(4) ?
O29 H29O . 0.845(10) ?
O30 C30 . 1.369(4) ?
O30 H30O . 0.841(10) ?
O31 C31 . 1.372(4) ?
O31 H31O . 0.836(10) ?
N4 C24 . 1.370(5) ?
N4 C17 . 1.396(5) ?
N4 H4N . 0.876(10) ?
N5 C25 . 1.289(5) ?
N5 N6 . 1.369(4) ?
N6 C26 . 1.344(5) ?
N6 H6N . 0.877(10) ?
C17 C18 . 1.360(5) ?
C17 C25 . 1.438(5) ?
C18 C19 . 1.419(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.403(5) ?
C19 C24 . 1.428(5) ?
C20 C21 . 1.374(5) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.397(6) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.369(5) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.383(5) ?
C23 H23 . 0.9500 ?
C25 H25 . 0.9500 ?
C26 C27 . 1.482(5) ?
C27 C28 . 1.382(5) ?
C27 C32 . 1.400(5) ?
C28 C29 . 1.383(5) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.388(5) ?
C30 C31 . 1.393(5) ?
C31 C32 . 1.370(5) ?
C32 H32 . 0.9500 ?
N7 C40 . 1.363(5) ?
N7 C33 . 1.376(5) ?
N7 H7N . 0.879(10) ?
N8 C41 . 1.286(5) ?
N8 N9 . 1.400(5) ?
N9 C42 . 1.290(5) ?
N10 C43 . 1.378(6) ?
N10 C50 . 1.380(5) ?
N10 H10N . 0.877(10) ?
C33 C34 . 1.371(6) ?
C33 C41 . 1.432(6) ?
C34 C35 . 1.416(6) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.394(6) ?
C35 C40 . 1.425(6) ?
C36 C37 . 1.386(6) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.409(6) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.375(6) ?
C38 H38 . 0.9500 ?
C39 C40 . 1.392(6) ?
C39 H39 . 0.9500 ?
C41 H41 . 0.9500 ?
C42 C43 . 1.414(6) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.371(6) ?
C44 C45 . 1.425(6) ?
C44 H44 . 0.9500 ?
C45 C50 . 1.405(6) ?
C45 C46 . 1.423(6) ?
C46 C47 . 1.367(7) ?
C46 H46 . 0.9500 ?
C47 C48 . 1.399(7) ?
C47 H47 . 0.9500 ?
C48 C49 . 1.367(6) ?
C48 H48 . 0.9500 ?
C49 C50 . 1.389(6) ?
C49 H49 . 0.9500 ?
O51 C51 . 1.427(5) ?
O51 H51O . 0.839(10) ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
O52 C52 . 1.440(5) ?
O52 H52O . 0.837(10) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
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
O13 H13O O14 . 0.844(10) 2.21(4) 2.674(4) 115(4)
O14 H14O O31 2_756 0.843(10) 1.979(19) 2.778(4) 158(4)
O14 H14O O15 . 0.843(10) 2.33(4) 2.763(4) 112(3)
O15 H15O O26 1_545 0.845(10) 1.773(11) 2.617(4) 179(4)
N1 H1N O51 2_666 0.884(10) 2.107(14) 2.976(4) 167(3)
N3 H3N O52 2_656 0.877(10) 2.129(15) 2.983(4) 165(4)
O29 H29O O30 2_866 0.845(10) 2.11(2) 2.858(4) 148(4)
O30 H30O O15 2_756 0.841(10) 1.911(15) 2.732(4) 165(4)
O31 H31O O10 . 0.836(10) 1.795(12) 2.626(4) 172(4)
N4 H4N O52 2_666 0.876(10) 2.118(12) 2.992(4) 175(3)
N6 H6N O51 2_666 0.877(10) 2.24(2) 3.011(4) 146(3)
O51 H51O O10 2_666 0.839(10) 2.21(3) 2.934(4) 145(4)
O51 H51O N2 2_666 0.839(10) 2.26(3) 2.975(4) 143(4)
O52 H52O N5 2_666 0.837(10) 2.29(3) 2.963(4) 138(4)
O52 H52O O26 2_666 0.837(10) 2.29(2) 3.046(4) 150(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655980
