N'-(2,3-Dihy-droxy-benzyl-idene)isonicotinohydrazide.

The title compound, C(13)H(11)N(3)O(3), crystallized with two independent mol-ecules in the asymmetric unit. One of the mol-ecules is twisted while the other is almost planar, with dihedral angles of 28.02 (6) and 2.42 (9)°, respectively, between the benzene and pyridine rings. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds are present in both mol-ecules. The two independent mol-ecules are linked by pairs of O-H⋯O hydrogen bonds. The crystal structure is further stabilized by inter-molecular N-H⋯N hydrogen bonds and C-H⋯N and C-H⋯O inter-actions.

Related literature

For the proven therapeutic importance of isonicotinic acid hydrazide, see: Agarwal et al. (2005 ▶, 2006 ▶); Savanini et al. (2002 ▶). For Schiff base complexes as models for biologically important species, see: Chohan & Sheazi (1999 ▶); Abou-Melha (2008 ▶). For the anti­tubercular activity of hydrazones, see: Durgaprasad & Patel (1973 ▶); Kriza et al. (2010 ▶). For hydrogen bonding leading to the dimerization of mol­ecules, see: Avasthi et al. (2002 ▶). For delocalized double bonds, see: Zülfikaroğlu et al. (2009 ▶).

Experimental

Crystal data

C13H11N3O3

M = 257.25

Monoclinic,

a = 7.7781 (2) Å

b = 30.0719 (8) Å

c = 10.5116 (3) Å

β = 101.551 (2)°

V = 2408.89 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.53 × 0.31 × 0.19 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.961, T max = 0.984

34859 measured reflections

5118 independent reflections

3512 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.084

S = 1.02

5118 reflections

432 parameters

All H-atom parameters refined

Δρmax = 0.14 e Å−3

Δρmin = −0.10 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048701/su2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048701/su2224Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11N3O3	F(000) = 1072
Mr = 257.25	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 29970 reflections
a = 7.7781 (2) Å	θ = 1.4–27.3°
b = 30.0719 (8) Å	µ = 0.10 mm−1
c = 10.5116 (3) Å	T = 296 K
β = 101.551 (2)°	Prism, yellow
V = 2408.89 (11) Å3	0.53 × 0.31 × 0.19 mm
Z = 8

Stoe IPDS-II diffractometer	5118 independent reflections
Radiation source: fine-focus sealed tube	3512 reflections with I > 2σ(I)
plane graphite	Rint = 0.049
w–scan rotation	θmax = 26.8°, θmin = 1.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.961, Tmax = 0.984	k = −37→37
34859 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	All H-atom parameters refined
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.005P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5118 reflections	Δρmax = 0.14 e Å−3
432 parameters	Δρmin = −0.10 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (6)

Experimental. Elemental analyses were performed using standard methods at TUBİTAK (The Turkish Scientific Research Centre). The IR spectrum was recorded on a Vertex 80v sample Compartment RT-DLaTGS spectrophotometer operating within 4000–500 cm-1. 1H NMR spectra were obtained on BRUKER DPX-400, 400 MHz High Performance Digital FT-NMR spectrometer using deuterated as solvent.Spectroscopic characterization of the title compound: The structure was verified by means of IR, 1H NMR (DMSO), UV-VIS spectral data and elemental analyses. In the 1H NMR spectra of I the azomethine proton appears as a singlet at 8.68 p.p.m.. A single resonance for the proton in –NHN= group is observed at 12.51 p.p.m.. Chemical shifts of the protons on the pyridine ring exhibit two sets of signals in 8.93–8.67 p.p.m. as a doublet and in 8.02–7.74 p.p.m. as doublet, too. The phenyl protons of 1 resonate at 7.07–6.70 p.p.m.. The protons of the phenolic OH are observed at 11.14 p.p.m. and 9.59 p.p.m. as singlets. The IR spectrum of the I shows a weak band at 3520 cm-1 assigned to ν OH of the phenolic group. The deformation vibration, δ of the phenolic OH groups appears at 1272 cm-1. The NH stretching absorption appears as strong band 3392 cm-1. Another important band occurs at 1680 cm-1 attributed to ν(C=0) (carbonyl) mode. Azomethine ν(C=N) absorption band appear at 1561 cm-1. The medium intensity band at 1061 cm-1 is ascribed to ν(N—N) vibration.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.34616 (19)	0.51866 (5)	0.32097 (13)	0.0431 (3)
C2	0.35373 (19)	0.56269 (5)	0.36519 (13)	0.0419 (3)
C3	0.4074 (2)	0.59653 (5)	0.29149 (14)	0.0462 (3)
C4	0.4506 (2)	0.58674 (6)	0.17444 (16)	0.0581 (4)
C5	0.4439 (3)	0.54342 (6)	0.12981 (17)	0.0640 (5)
C6	0.3938 (2)	0.50971 (6)	0.20279 (16)	0.0568 (4)
C7	0.2901 (2)	0.48325 (5)	0.39706 (14)	0.0453 (3)
C8	0.14430 (19)	0.47313 (4)	0.68980 (14)	0.0444 (3)
C9	0.08913 (19)	0.43654 (4)	0.77030 (13)	0.0420 (3)
C10	0.0715 (2)	0.39237 (5)	0.73485 (15)	0.0534 (4)
C11	0.0135 (2)	0.36246 (5)	0.81626 (15)	0.0540 (4)
C12	−0.0071 (3)	0.41568 (5)	0.96253 (16)	0.0599 (4)
C13	0.0503 (2)	0.44791 (5)	0.88844 (15)	0.0547 (4)
C14	0.4163 (2)	0.72836 (5)	0.73128 (14)	0.0449 (3)
C15	0.41093 (19)	0.68485 (4)	0.68380 (13)	0.0422 (3)
C16	0.5024 (2)	0.65111 (5)	0.76002 (14)	0.0480 (4)
C17	0.5992 (2)	0.66094 (6)	0.88134 (16)	0.0566 (4)
C18	0.6080 (3)	0.70385 (6)	0.92819 (17)	0.0643 (5)
C19	0.5175 (2)	0.73716 (6)	0.85442 (16)	0.0585 (4)
C20	0.3177 (2)	0.76380 (5)	0.65502 (15)	0.0484 (4)
C21	0.0455 (2)	0.77429 (5)	0.34901 (14)	0.0464 (4)
C22	−0.0175 (2)	0.81153 (4)	0.25675 (14)	0.0435 (3)
C23	0.0552 (2)	0.85359 (5)	0.26961 (15)	0.0464 (3)
C24	−0.0049 (2)	0.88488 (5)	0.17529 (15)	0.0525 (4)
C25	−0.1971 (3)	0.83591 (6)	0.05928 (17)	0.0614 (4)
C26	−0.1452 (2)	0.80275 (5)	0.14845 (16)	0.0558 (4)
N1	0.24130 (16)	0.49326 (4)	0.50259 (11)	0.0446 (3)
N2	0.18813 (17)	0.46034 (4)	0.57653 (12)	0.0458 (3)
N3	−0.02774 (18)	0.37320 (4)	0.92838 (12)	0.0526 (3)
N4	0.22153 (17)	0.75411 (4)	0.54531 (11)	0.0472 (3)
N5	0.13318 (18)	0.78684 (4)	0.46848 (12)	0.0494 (3)
N6	−0.12988 (19)	0.87675 (4)	0.07101 (12)	0.0563 (3)
O1	0.30926 (15)	0.57472 (3)	0.47939 (9)	0.0522 (3)
O2	0.41509 (17)	0.63953 (3)	0.33438 (11)	0.0598 (3)
O3	0.14895 (16)	0.51167 (3)	0.72583 (10)	0.0587 (3)
O4	0.31740 (15)	0.67309 (3)	0.56449 (9)	0.0512 (3)
O5	0.49762 (18)	0.60853 (4)	0.71623 (12)	0.0666 (3)
O6	0.02582 (17)	0.73564 (3)	0.31578 (10)	0.0636 (3)
H1O	0.276 (3)	0.5475 (7)	0.5152 (19)	0.090 (6)*
H2N	0.180 (2)	0.4320 (6)	0.5448 (15)	0.057 (5)*
H2O	0.375 (3)	0.6411 (7)	0.415 (2)	0.099 (7)*
H4	0.486 (2)	0.6103 (6)	0.1235 (15)	0.061 (5)*
H4O	0.260 (3)	0.7006 (8)	0.531 (2)	0.095 (7)*
H5	0.472 (2)	0.5371 (6)	0.0478 (18)	0.077 (5)*
H5N	0.128 (2)	0.8148 (6)	0.4980 (16)	0.059 (5)*
H5O	0.427 (3)	0.6065 (8)	0.636 (2)	0.106 (8)*
H6	0.390 (2)	0.4797 (6)	0.1748 (15)	0.060 (5)*
H7	0.294 (2)	0.4536 (5)	0.3685 (14)	0.051 (4)*
H10	0.096 (2)	0.3824 (6)	0.6532 (17)	0.066 (5)*
H11	0.003 (2)	0.3318 (6)	0.7931 (15)	0.061 (5)*
H12	−0.034 (2)	0.4237 (6)	1.0435 (18)	0.074 (5)*
H13	0.060 (2)	0.4793 (6)	0.9133 (16)	0.068 (5)*
H17	0.661 (2)	0.6365 (6)	0.9290 (16)	0.064 (5)*
H18	0.679 (2)	0.7098 (6)	1.0143 (18)	0.073 (5)*
H19	0.522 (2)	0.7674 (6)	0.8835 (16)	0.071 (5)*
H20	0.325 (2)	0.7937 (6)	0.6894 (15)	0.060 (5)*
H23	0.151 (2)	0.8611 (5)	0.3421 (15)	0.052 (4)*
H24	0.043 (2)	0.9140 (6)	0.1819 (16)	0.064 (5)*
H25	−0.286 (3)	0.8311 (6)	−0.0207 (19)	0.082 (6)*
H26	−0.199 (2)	0.7732 (6)	0.1373 (16)	0.064 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0451 (8)	0.0384 (7)	0.0454 (7)	0.0024 (6)	0.0085 (6)	0.0008 (6)
C2	0.0449 (8)	0.0393 (7)	0.0405 (7)	0.0000 (6)	0.0060 (6)	0.0019 (6)
C3	0.0504 (9)	0.0391 (8)	0.0478 (8)	0.0000 (6)	0.0071 (7)	0.0057 (6)
C4	0.0643 (11)	0.0556 (10)	0.0587 (10)	0.0014 (8)	0.0227 (8)	0.0135 (8)
C5	0.0803 (13)	0.0641 (11)	0.0557 (9)	0.0077 (9)	0.0331 (9)	0.0021 (8)
C6	0.0709 (11)	0.0454 (9)	0.0583 (9)	0.0057 (8)	0.0228 (8)	−0.0051 (7)
C7	0.0523 (9)	0.0330 (8)	0.0504 (8)	0.0006 (6)	0.0096 (7)	−0.0012 (6)
C8	0.0508 (9)	0.0330 (7)	0.0490 (8)	0.0004 (6)	0.0086 (7)	0.0007 (6)
C9	0.0443 (8)	0.0353 (7)	0.0457 (7)	0.0011 (6)	0.0078 (6)	0.0011 (6)
C10	0.0756 (11)	0.0383 (8)	0.0504 (9)	−0.0048 (8)	0.0228 (8)	−0.0033 (7)
C11	0.0726 (11)	0.0340 (8)	0.0569 (9)	−0.0064 (7)	0.0165 (8)	−0.0012 (7)
C12	0.0894 (13)	0.0462 (9)	0.0480 (9)	−0.0041 (9)	0.0228 (9)	−0.0016 (7)
C13	0.0771 (12)	0.0376 (8)	0.0521 (9)	−0.0036 (8)	0.0190 (8)	−0.0030 (7)
C14	0.0509 (9)	0.0400 (8)	0.0460 (8)	−0.0012 (7)	0.0151 (7)	−0.0035 (6)
C15	0.0480 (8)	0.0393 (8)	0.0402 (7)	−0.0011 (6)	0.0113 (6)	−0.0011 (6)
C16	0.0543 (9)	0.0399 (8)	0.0498 (8)	0.0008 (7)	0.0106 (7)	−0.0004 (6)
C17	0.0580 (11)	0.0562 (10)	0.0529 (9)	0.0070 (8)	0.0044 (8)	0.0055 (8)
C18	0.0656 (11)	0.0689 (12)	0.0523 (10)	0.0003 (9)	−0.0028 (9)	−0.0103 (9)
C19	0.0667 (11)	0.0513 (10)	0.0561 (9)	−0.0041 (8)	0.0087 (8)	−0.0145 (8)
C20	0.0622 (10)	0.0353 (8)	0.0509 (9)	0.0000 (7)	0.0188 (8)	−0.0049 (7)
C21	0.0629 (10)	0.0325 (7)	0.0479 (8)	0.0024 (7)	0.0208 (7)	−0.0017 (6)
C22	0.0539 (9)	0.0339 (7)	0.0467 (8)	0.0035 (6)	0.0195 (7)	−0.0021 (6)
C23	0.0599 (10)	0.0353 (8)	0.0463 (8)	0.0003 (7)	0.0165 (8)	−0.0019 (6)
C24	0.0754 (11)	0.0338 (8)	0.0520 (9)	−0.0014 (8)	0.0213 (8)	−0.0002 (7)
C25	0.0696 (12)	0.0520 (10)	0.0585 (10)	−0.0008 (8)	0.0028 (9)	0.0043 (8)
C26	0.0663 (11)	0.0400 (9)	0.0599 (10)	−0.0082 (8)	0.0096 (8)	−0.0003 (7)
N1	0.0524 (7)	0.0340 (6)	0.0469 (7)	−0.0034 (5)	0.0092 (6)	0.0050 (5)
N2	0.0602 (8)	0.0308 (6)	0.0474 (7)	−0.0044 (6)	0.0133 (6)	0.0021 (5)
N3	0.0655 (9)	0.0425 (7)	0.0501 (7)	−0.0038 (6)	0.0123 (6)	0.0053 (6)
N4	0.0638 (8)	0.0335 (6)	0.0472 (7)	0.0073 (6)	0.0179 (6)	0.0023 (5)
N5	0.0726 (9)	0.0303 (6)	0.0463 (7)	0.0102 (6)	0.0141 (6)	0.0002 (5)
N6	0.0732 (9)	0.0437 (7)	0.0533 (8)	0.0070 (7)	0.0156 (7)	0.0053 (6)
O1	0.0784 (8)	0.0367 (6)	0.0438 (5)	−0.0078 (5)	0.0173 (5)	−0.0032 (4)
O2	0.0840 (8)	0.0379 (6)	0.0586 (7)	−0.0085 (5)	0.0171 (6)	0.0042 (5)
O3	0.0850 (8)	0.0314 (5)	0.0626 (6)	−0.0013 (5)	0.0219 (6)	−0.0019 (5)
O4	0.0701 (7)	0.0362 (5)	0.0437 (5)	0.0066 (5)	0.0029 (5)	−0.0044 (4)
O5	0.0877 (9)	0.0389 (6)	0.0653 (8)	0.0103 (6)	−0.0038 (7)	−0.0001 (5)
O6	0.0994 (9)	0.0308 (6)	0.0602 (7)	0.0008 (6)	0.0149 (6)	−0.0044 (5)

C1—C6	1.392 (2)	C15—C16	1.396 (2)
C1—C2	1.4005 (19)	C16—O5	1.3589 (18)
C1—C7	1.450 (2)	C16—C17	1.377 (2)
C2—O1	1.3630 (17)	C17—C18	1.378 (2)
C2—C3	1.3925 (19)	C17—H17	0.961 (18)
C3—O2	1.3669 (18)	C18—C19	1.372 (3)
C3—C4	1.371 (2)	C18—H18	0.979 (19)
C4—C5	1.382 (2)	C19—H19	0.958 (19)
C4—H4	0.961 (17)	C20—N4	1.276 (2)
C5—C6	1.374 (2)	C20—H20	0.967 (17)
C5—H5	0.951 (19)	C21—O6	1.2145 (17)
C6—H6	0.949 (17)	C21—N5	1.3571 (19)
C7—N1	1.2782 (18)	C21—C22	1.498 (2)
C7—H7	0.943 (16)	C22—C26	1.378 (2)
C8—O3	1.2174 (16)	C22—C23	1.381 (2)
C8—N2	1.3582 (18)	C23—C24	1.379 (2)
C8—C9	1.5023 (19)	C23—H23	0.979 (16)
C9—C13	1.379 (2)	C24—N6	1.334 (2)
C9—C10	1.379 (2)	C24—H24	0.950 (18)
C10—C11	1.378 (2)	C25—N6	1.331 (2)
C10—H10	0.964 (17)	C25—C26	1.373 (2)
C11—N3	1.322 (2)	C25—H25	0.99 (2)
C11—H11	0.952 (17)	C26—H26	0.977 (18)
C12—N3	1.328 (2)	N1—N2	1.3726 (15)
C12—C13	1.373 (2)	N2—H2N	0.912 (17)
C12—H12	0.946 (18)	N4—N5	1.3679 (16)
C13—H13	0.977 (18)	N5—H5N	0.901 (17)
C14—C15	1.3981 (19)	O1—H1O	0.96 (2)
C14—C19	1.399 (2)	O2—H2O	0.96 (2)
C14—C20	1.456 (2)	O4—H4O	0.97 (2)
C15—O4	1.3644 (17)	O5—H5O	0.91 (2)
C6—C1—C2	118.56 (13)	O5—C16—C15	120.95 (13)
C6—C1—C7	120.89 (14)	C17—C16—C15	119.80 (14)
C2—C1—C7	120.56 (13)	C16—C17—C18	120.71 (16)
O1—C2—C3	116.93 (12)	C16—C17—H17	116.3 (10)
O1—C2—C1	122.82 (12)	C18—C17—H17	123.0 (10)
C3—C2—C1	120.24 (13)	C19—C18—C17	119.92 (16)
O2—C3—C4	119.77 (13)	C19—C18—H18	121.4 (11)
O2—C3—C2	120.41 (13)	C17—C18—H18	118.7 (11)
C4—C3—C2	119.81 (14)	C18—C19—C14	120.99 (16)
C3—C4—C5	120.50 (15)	C18—C19—H19	122.2 (11)
C3—C4—H4	119.4 (10)	C14—C19—H19	116.8 (11)
C5—C4—H4	120.1 (10)	N4—C20—C14	118.63 (13)
C6—C5—C4	120.10 (16)	N4—C20—H20	122.1 (10)
C6—C5—H5	120.2 (11)	C14—C20—H20	119.3 (10)
C4—C5—H5	119.7 (11)	O6—C21—N5	122.91 (14)
C5—C6—C1	120.77 (16)	O6—C21—C22	121.54 (14)
C5—C6—H6	121.7 (10)	N5—C21—C22	115.46 (12)
C1—C6—H6	117.6 (10)	C26—C22—C23	118.00 (14)
N1—C7—C1	118.68 (13)	C26—C22—C21	118.68 (13)
N1—C7—H7	122.3 (9)	C23—C22—C21	123.15 (14)
C1—C7—H7	119.0 (9)	C24—C23—C22	118.79 (15)
O3—C8—N2	123.06 (13)	C24—C23—H23	119.8 (9)
O3—C8—C9	121.07 (13)	C22—C23—H23	121.4 (9)
N2—C8—C9	115.87 (12)	N6—C24—C23	123.50 (15)
C13—C9—C10	117.05 (14)	N6—C24—H24	116.1 (10)
C13—C9—C8	117.67 (13)	C23—C24—H24	120.4 (10)
C10—C9—C8	125.28 (13)	N6—C25—C26	123.41 (17)
C11—C10—C9	119.21 (14)	N6—C25—H25	114.1 (11)
C11—C10—H10	119.9 (10)	C26—C25—H25	122.5 (11)
C9—C10—H10	120.9 (10)	C25—C26—C22	119.33 (16)
N3—C11—C10	124.20 (15)	C25—C26—H26	121.2 (10)
N3—C11—H11	116.2 (10)	C22—C26—H26	119.4 (10)
C10—C11—H11	119.6 (10)	C7—N1—N2	119.80 (12)
N3—C12—C13	124.13 (15)	C8—N2—N1	116.67 (12)
N3—C12—H12	116.8 (11)	C8—N2—H2N	125.0 (10)
C13—C12—H12	119.1 (11)	N1—N2—H2N	118.2 (10)
C12—C13—C9	119.38 (15)	C11—N3—C12	116.00 (13)
C12—C13—H13	123.0 (10)	C20—N4—N5	120.22 (12)
C9—C13—H13	117.5 (10)	C21—N5—N4	116.50 (12)
C15—C14—C19	118.58 (14)	C21—N5—H5N	122.0 (11)
C15—C14—C20	120.91 (13)	N4—N5—H5N	121.4 (11)
C19—C14—C20	120.51 (14)	C25—N6—C24	116.96 (14)
O4—C15—C16	117.12 (12)	C2—O1—H1O	104.8 (12)
O4—C15—C14	122.88 (13)	C3—O2—H2O	109.8 (13)
C16—C15—C14	119.99 (13)	C15—O4—H4O	103.7 (12)
O5—C16—C17	119.26 (14)	C16—O5—H5O	110.2 (15)
C6—C1—C2—O1	179.80 (14)	O4—C15—C16—C17	179.97 (14)
C7—C1—C2—O1	−0.3 (2)	C14—C15—C16—C17	−0.7 (2)
C6—C1—C2—C3	0.2 (2)	O5—C16—C17—C18	179.45 (16)
C7—C1—C2—C3	−179.86 (13)	C15—C16—C17—C18	−0.5 (2)
O1—C2—C3—O2	0.5 (2)	C16—C17—C18—C19	1.0 (3)
C1—C2—C3—O2	−179.93 (14)	C17—C18—C19—C14	−0.3 (3)
O1—C2—C3—C4	−178.75 (14)	C15—C14—C19—C18	−0.8 (2)
C1—C2—C3—C4	0.9 (2)	C20—C14—C19—C18	178.64 (16)
O2—C3—C4—C5	179.84 (16)	C15—C14—C20—N4	2.2 (2)
C2—C3—C4—C5	−0.9 (3)	C19—C14—C20—N4	−177.30 (15)
C3—C4—C5—C6	−0.1 (3)	O6—C21—C22—C26	20.5 (2)
C4—C5—C6—C1	1.1 (3)	N5—C21—C22—C26	−162.84 (14)
C2—C1—C6—C5	−1.2 (2)	O6—C21—C22—C23	−154.54 (15)
C7—C1—C6—C5	178.86 (16)	N5—C21—C22—C23	22.1 (2)
C6—C1—C7—N1	−177.40 (15)	C26—C22—C23—C24	1.0 (2)
C2—C1—C7—N1	2.7 (2)	C21—C22—C23—C24	176.10 (14)
O3—C8—C9—C13	−2.3 (2)	C22—C23—C24—N6	−0.3 (2)
N2—C8—C9—C13	177.47 (14)	N6—C25—C26—C22	0.3 (3)
O3—C8—C9—C10	176.64 (16)	C23—C22—C26—C25	−1.0 (2)
N2—C8—C9—C10	−3.5 (2)	C21—C22—C26—C25	−176.33 (15)
C13—C9—C10—C11	1.4 (2)	C1—C7—N1—N2	−179.80 (13)
C8—C9—C10—C11	−177.64 (16)	O3—C8—N2—N1	0.7 (2)
C9—C10—C11—N3	0.1 (3)	C9—C8—N2—N1	−179.09 (12)
N3—C12—C13—C9	0.4 (3)	C7—N1—N2—C8	177.63 (14)
C10—C9—C13—C12	−1.6 (2)	C10—C11—N3—C12	−1.3 (3)
C8—C9—C13—C12	177.49 (16)	C13—C12—N3—C11	1.0 (3)
C19—C14—C15—O4	−179.38 (14)	C14—C20—N4—N5	−177.10 (13)
C20—C14—C15—O4	1.2 (2)	O6—C21—N5—N4	9.1 (2)
C19—C14—C15—C16	1.3 (2)	C22—C21—N5—N4	−167.49 (12)
C20—C14—C15—C16	−178.15 (14)	C20—N4—N5—C21	174.77 (14)
O4—C15—C16—O5	0.0 (2)	C26—C25—N6—C24	0.5 (3)
C14—C15—C16—O5	179.39 (14)	C23—C24—N6—C25	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.96 (2)	1.65 (2)	2.5281 (15)	149.7 (18)
N2—H2N···N6i	0.913 (18)	2.051 (17)	2.9407 (17)	164.7 (15)
O2—H2O···O1	0.96 (2)	2.20 (2)	2.7022 (14)	111.3 (15)
O2—H2O···O4	0.96 (2)	1.97 (2)	2.8605 (15)	153.3 (18)
O4—H4O···N4	0.97 (2)	1.65 (2)	2.5441 (15)	151.2 (19)
N5—H5N···N3ii	0.900 (18)	2.129 (17)	2.9914 (18)	160.2 (14)
O5—H5O···O1	0.91 (2)	1.96 (2)	2.8138 (16)	154 (2)
O5—H5O···O4	0.91 (2)	2.25 (2)	2.7171 (16)	111.6 (18)
C10—H10···N6i	0.964 (17)	2.429 (17)	3.369 (2)	164.8 (15)
C11—H11···O6iii	0.953 (18)	2.317 (18)	3.2485 (18)	165.4 (13)
C20—H20···O2iv	0.967 (18)	2.533 (17)	3.4652 (18)	162.0 (13)
C24—H24···O3v	0.949 (18)	2.395 (18)	3.3373 (18)	172.1 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.96 (2)	1.65 (2)	2.5281 (15)	149.7 (18)
N2—H2N⋯N6i	0.913 (18)	2.051 (17)	2.9407 (17)	164.7 (15)
O2—H2O⋯O1	0.96 (2)	2.20 (2)	2.7022 (14)	111.3 (15)
O2—H2O⋯O4	0.96 (2)	1.97 (2)	2.8605 (15)	153.3 (18)
O4—H4O⋯N4	0.97 (2)	1.65 (2)	2.5441 (15)	151.2 (19)
N5—H5N⋯N3ii	0.900 (18)	2.129 (17)	2.9914 (18)	160.2 (14)
O5—H5O⋯O1	0.91 (2)	1.96 (2)	2.8138 (16)	154 (2)
O5—H5O⋯O4	0.91 (2)	2.25 (2)	2.7171 (16)	111.6 (18)
C10—H10⋯N6i	0.964 (17)	2.429 (17)	3.369 (2)	164.8 (15)
C11—H11⋯O6iii	0.953 (18)	2.317 (18)	3.2485 (18)	165.4 (13)
C20—H20⋯O2iv	0.967 (18)	2.533 (17)	3.4652 (18)	162.0 (13)
C24—H24⋯O3v	0.949 (18)	2.395 (18)	3.3373 (18)	172.1 (14)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .