N'-[(E)-1-(2-Hy-droxy-phen-yl)ethyl-idene]pyrazine-2-carbohydrazide.

The title compound, C13H12N4O2, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. Mol-ecule B is planar to within 0.044 (3) Å for all non-H atoms, while mol-ecule A is slightly twisted, with a dihedral angle of 6.29 (4)° between the mean planes of the pyrazine-2-carbohydrazide and 1-(2-hy-droxy-phen-yl)ethanone moieties (r.m.s. deviations = 0.0348 and 0.0428 Å, respectively). S(5) and S(6) ring motifs are formed in both mol-ecules due to the presence of intra-molecular O-H⋯N and N-H⋯N hydrogen bonds. In the crystal, mol-ecules A and B are linked by a C-H⋯O hydrogen bond. They stack along the a-axis direction, forming columns with π-π inter-actions involving inversion-related pyrazine and benzene rings [centroid-centroid distances = 3.5489 (13)-3.8513 (16) Å].

Related literature

For a related crystal structure and other studies, see: Hameed et al. (2013 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H12N4O2

M = 256.27

Triclinic,

a = 7.1767 (7) Å

b = 10.1743 (10) Å

c = 17.1150 (17) Å

α = 86.172 (3)°

β = 85.275 (2)°

γ = 80.963 (4)°

V = 1228.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.28 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.981

19042 measured reflections

4821 independent reflections

2608 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.00

4821 reflections

361 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813022137/su2634sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022137/su2634Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022137/su2634Isup3.cml

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

C13H12N4O2	Z = 4
Mr = 256.27	F(000) = 536
Triclinic, P1	Dx = 1.386 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1767 (7) Å	Cell parameters from 2608 reflections
b = 10.1743 (10) Å	θ = 1.2–26.0°
c = 17.1150 (17) Å	µ = 0.10 mm−1
α = 86.172 (3)°	T = 296 K
β = 85.275 (2)°	Prism, colourless
γ = 80.963 (4)°	0.28 × 0.23 × 0.20 mm
V = 1228.2 (2) Å3

Bruker Kappa APEXII CCD diffractometer	4821 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 1.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.973, Tmax = 0.981	l = −21→21
19042 measured reflections

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2363P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4821 reflections	Δρmax = 0.23 e Å−3
361 parameters	Δρmin = −0.16 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: 0.0083 (12)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.4150 (3)	0.07549 (16)	−0.16151 (9)	0.0602 (7)
O2	0.2080 (2)	−0.19271 (16)	−0.05633 (10)	0.0582 (6)
N1	0.2781 (2)	0.04641 (18)	−0.02111 (10)	0.0372 (6)
N2	0.2155 (3)	−0.04221 (18)	0.03446 (11)	0.0398 (7)
N3	0.0878 (2)	−0.20255 (18)	0.14825 (12)	0.0456 (7)
N4	0.0423 (3)	−0.46305 (19)	0.11955 (14)	0.0545 (8)
C1	0.4198 (3)	0.2026 (2)	−0.14404 (14)	0.0421 (8)
C2	0.4732 (3)	0.2888 (3)	−0.20396 (15)	0.0561 (10)
C3	0.4803 (3)	0.4192 (3)	−0.19149 (17)	0.0604 (11)
C4	0.4368 (3)	0.4658 (2)	−0.11752 (17)	0.0560 (10)
C5	0.3875 (3)	0.3803 (2)	−0.05687 (14)	0.0448 (8)
C6	0.3735 (3)	0.2475 (2)	−0.06741 (13)	0.0358 (7)
C7	0.3094 (3)	0.1610 (2)	−0.00190 (12)	0.0352 (7)
C8	0.2827 (3)	0.2063 (2)	0.08019 (13)	0.0515 (9)
C9	0.1834 (3)	−0.1606 (2)	0.01156 (14)	0.0382 (8)
C10	0.1186 (3)	−0.2501 (2)	0.07671 (13)	0.0371 (8)
C11	0.0343 (3)	−0.2871 (3)	0.20495 (16)	0.0561 (10)
C12	0.0136 (3)	−0.4158 (3)	0.19042 (17)	0.0573 (10)
C13	0.0928 (3)	−0.3772 (2)	0.06276 (15)	0.0469 (9)
O3	0.2432 (3)	0.48626 (18)	0.34993 (10)	0.0754 (8)
O4	0.1729 (3)	0.7739 (2)	0.48091 (12)	0.0870 (9)
N5	0.2460 (3)	0.5031 (2)	0.49687 (11)	0.0491 (7)
N6	0.2206 (3)	0.5847 (2)	0.55841 (12)	0.0557 (8)
N7	0.1834 (3)	0.7165 (2)	0.68710 (12)	0.0550 (8)
N8	0.0968 (3)	0.9941 (2)	0.68391 (16)	0.0754 (10)
C14	0.2858 (3)	0.3535 (3)	0.36491 (14)	0.0500 (9)
C15	0.3115 (4)	0.2738 (3)	0.30127 (15)	0.0617 (11)
C16	0.3510 (4)	0.1389 (3)	0.31072 (17)	0.0671 (11)
C17	0.3662 (4)	0.0795 (3)	0.38440 (19)	0.0747 (11)
C18	0.3421 (4)	0.1569 (3)	0.44851 (16)	0.0682 (11)
C19	0.3018 (3)	0.2958 (2)	0.44095 (13)	0.0454 (8)
C20	0.2773 (3)	0.3760 (3)	0.51033 (13)	0.0496 (9)
C21	0.2897 (7)	0.3111 (4)	0.5907 (2)	0.104 (2)
C22	0.1843 (4)	0.7184 (3)	0.54528 (16)	0.0556 (10)
C23	0.1605 (3)	0.7897 (3)	0.62001 (15)	0.0502 (9)
C24	0.1623 (4)	0.7838 (3)	0.75194 (15)	0.0633 (10)
C25	0.1216 (4)	0.9200 (3)	0.74989 (18)	0.0689 (11)
C26	0.1158 (4)	0.9267 (3)	0.61878 (17)	0.0693 (11)
H1	0.36890	0.03550	−0.12340	0.0900*
H2	0.50520	0.25780	−0.25390	0.0670*
H2A	0.202 (3)	−0.031 (2)	0.0805 (13)	0.0480*
H3	0.51450	0.47650	−0.23300	0.0720*
H4	0.44080	0.55450	−0.10880	0.0670*
H5	0.36250	0.41190	−0.00680	0.0540*
H8A	0.27220	0.13110	0.11640	0.0770*
H8B	0.16950	0.27020	0.08570	0.0770*
H8C	0.38940	0.24660	0.09110	0.0770*
H11	0.01000	−0.25890	0.25590	0.0670*
H12	−0.02200	−0.47180	0.23230	0.0690*
H13	0.11150	−0.40420	0.01150	0.0560*
H3A	0.23690	0.52440	0.39100	0.1130*
H6	0.234 (4)	0.557 (3)	0.6029 (15)	0.0670*
H15	0.30140	0.31340	0.25090	0.0740*
H16	0.36760	0.08720	0.26720	0.0810*
H17	0.39280	−0.01280	0.39120	0.0900*
H18	0.35300	0.11540	0.49840	0.0820*
H21A	0.250 (6)	0.367 (4)	0.628 (3)	0.1560*
H21B	0.409 (6)	0.269 (4)	0.598 (2)	0.1560*
H21C	0.210 (6)	0.246 (4)	0.597 (2)	0.1560*
H24	0.17570	0.73700	0.80020	0.0760*
H25	0.11100	0.96230	0.79690	0.0820*
H26	0.09830	0.97380	0.57080	0.0830*

	U11	U22	U33	U12	U13	U23
O1	0.0827 (13)	0.0529 (11)	0.0456 (11)	−0.0117 (9)	0.0008 (9)	−0.0108 (9)
O2	0.0818 (12)	0.0506 (10)	0.0459 (11)	−0.0196 (9)	−0.0032 (9)	−0.0089 (9)
N1	0.0369 (10)	0.0324 (10)	0.0419 (11)	−0.0046 (8)	−0.0035 (8)	0.0004 (9)
N2	0.0458 (11)	0.0354 (11)	0.0388 (12)	−0.0082 (8)	−0.0029 (9)	−0.0019 (10)
N3	0.0471 (11)	0.0425 (12)	0.0472 (13)	−0.0096 (9)	−0.0004 (9)	−0.0001 (10)
N4	0.0479 (12)	0.0366 (12)	0.0775 (17)	−0.0067 (9)	−0.0032 (11)	0.0063 (12)
C1	0.0404 (13)	0.0423 (14)	0.0440 (15)	−0.0061 (10)	−0.0073 (10)	−0.0003 (12)
C2	0.0533 (16)	0.0713 (19)	0.0426 (16)	−0.0109 (13)	−0.0040 (12)	0.0079 (14)
C3	0.0508 (16)	0.066 (2)	0.066 (2)	−0.0227 (13)	−0.0113 (14)	0.0253 (16)
C4	0.0527 (15)	0.0438 (15)	0.075 (2)	−0.0178 (12)	−0.0159 (14)	0.0102 (15)
C5	0.0430 (13)	0.0397 (14)	0.0530 (16)	−0.0082 (10)	−0.0080 (11)	−0.0020 (12)
C6	0.0310 (11)	0.0341 (13)	0.0418 (14)	−0.0024 (9)	−0.0072 (9)	0.0012 (10)
C7	0.0321 (11)	0.0322 (13)	0.0409 (14)	−0.0008 (9)	−0.0061 (9)	−0.0049 (10)
C8	0.0696 (16)	0.0409 (14)	0.0450 (15)	−0.0124 (12)	−0.0007 (12)	−0.0045 (12)
C9	0.0372 (12)	0.0332 (13)	0.0449 (15)	−0.0032 (10)	−0.0080 (10)	−0.0054 (11)
C10	0.0305 (11)	0.0331 (13)	0.0468 (15)	−0.0021 (9)	−0.0048 (10)	−0.0005 (11)
C11	0.0584 (16)	0.0580 (17)	0.0517 (17)	−0.0135 (13)	0.0022 (12)	0.0015 (14)
C12	0.0470 (15)	0.0517 (17)	0.071 (2)	−0.0116 (12)	0.0003 (13)	0.0166 (15)
C13	0.0451 (14)	0.0353 (14)	0.0600 (17)	−0.0040 (11)	−0.0044 (12)	−0.0044 (13)
O3	0.1333 (18)	0.0556 (12)	0.0381 (11)	−0.0212 (11)	0.0008 (11)	−0.0001 (9)
O4	0.148 (2)	0.0666 (13)	0.0462 (13)	−0.0209 (13)	−0.0017 (12)	0.0016 (11)
N5	0.0622 (13)	0.0506 (13)	0.0357 (12)	−0.0122 (10)	0.0009 (9)	−0.0085 (10)
N6	0.0763 (15)	0.0575 (15)	0.0338 (12)	−0.0110 (11)	−0.0004 (11)	−0.0090 (12)
N7	0.0584 (13)	0.0605 (14)	0.0467 (14)	−0.0059 (10)	−0.0033 (10)	−0.0146 (12)
N8	0.0934 (19)	0.0602 (16)	0.0776 (19)	−0.0186 (13)	−0.0074 (15)	−0.0238 (15)
C14	0.0542 (15)	0.0568 (17)	0.0399 (15)	−0.0139 (12)	0.0040 (11)	−0.0066 (13)
C15	0.0750 (19)	0.071 (2)	0.0413 (16)	−0.0182 (15)	0.0036 (13)	−0.0133 (14)
C16	0.0650 (18)	0.080 (2)	0.058 (2)	−0.0068 (15)	−0.0027 (14)	−0.0279 (17)
C17	0.092 (2)	0.0533 (17)	0.077 (2)	0.0073 (15)	−0.0161 (17)	−0.0223 (17)
C18	0.087 (2)	0.0600 (19)	0.0557 (18)	−0.0001 (15)	−0.0147 (15)	−0.0041 (15)
C19	0.0470 (14)	0.0497 (15)	0.0397 (15)	−0.0068 (11)	−0.0023 (11)	−0.0055 (12)
C20	0.0567 (15)	0.0554 (17)	0.0361 (14)	−0.0074 (12)	−0.0025 (11)	−0.0026 (12)
C21	0.194 (5)	0.072 (3)	0.0387 (19)	0.002 (3)	−0.011 (2)	0.0014 (17)
C22	0.0675 (17)	0.0532 (18)	0.0481 (18)	−0.0152 (13)	−0.0005 (13)	−0.0078 (14)
C23	0.0532 (15)	0.0532 (16)	0.0468 (17)	−0.0140 (12)	−0.0013 (12)	−0.0101 (13)
C24	0.0668 (17)	0.075 (2)	0.0491 (17)	−0.0044 (14)	−0.0086 (13)	−0.0206 (15)
C25	0.0684 (19)	0.076 (2)	0.066 (2)	−0.0119 (16)	−0.0047 (15)	−0.0304 (18)
C26	0.091 (2)	0.0570 (19)	0.063 (2)	−0.0200 (15)	−0.0050 (15)	−0.0071 (16)

O1—C1	1.353 (3)	C11—C12	1.382 (4)
O2—C9	1.219 (3)	C2—H2	0.9300
O1—H1	0.8200	C3—H3	0.9300
O3—C14	1.349 (3)	C4—H4	0.9300
O4—C22	1.207 (3)	C5—H5	0.9300
O3—H3A	0.8200	C8—H8B	0.9600
N1—N2	1.364 (3)	C8—H8C	0.9600
N1—C7	1.290 (3)	C8—H8A	0.9600
N2—C9	1.350 (3)	C11—H11	0.9300
N3—C11	1.327 (3)	C12—H12	0.9300
N3—C10	1.335 (3)	C13—H13	0.9300
N4—C13	1.329 (3)	C14—C15	1.384 (4)
N4—C12	1.323 (4)	C14—C19	1.398 (3)
N2—H2A	0.80 (2)	C15—C16	1.359 (4)
N5—N6	1.367 (3)	C16—C17	1.367 (4)
N5—C20	1.286 (4)	C17—C18	1.377 (4)
N6—C22	1.351 (4)	C18—C19	1.397 (4)
N7—C24	1.328 (3)	C19—C20	1.469 (3)
N7—C23	1.334 (3)	C20—C21	1.489 (4)
N8—C25	1.324 (4)	C22—C23	1.497 (4)
N8—C26	1.334 (4)	C23—C26	1.380 (4)
N6—H6	0.80 (3)	C24—C25	1.369 (4)
C1—C6	1.414 (3)	C15—H15	0.9300
C1—C2	1.374 (4)	C16—H16	0.9300
C2—C3	1.367 (4)	C17—H17	0.9300
C3—C4	1.376 (4)	C18—H18	0.9300
C4—C5	1.369 (3)	C21—H21A	0.88 (5)
C5—C6	1.395 (3)	C21—H21B	0.91 (4)
C6—C7	1.468 (3)	C21—H21C	0.94 (4)
C7—C8	1.496 (3)	C24—H24	0.9300
C9—C10	1.484 (3)	C25—H25	0.9300
C10—C13	1.374 (3)	C26—H26	0.9300
C1—O1—H1	109.00	C7—C8—H8A	109.00
C14—O3—H3A	110.00	N3—C11—H11	119.00
N2—N1—C7	120.53 (18)	C12—C11—H11	119.00
N1—N2—C9	118.47 (18)	N4—C12—H12	118.00
C10—N3—C11	115.5 (2)	C11—C12—H12	119.00
C12—N4—C13	115.0 (2)	C10—C13—H13	119.00
C9—N2—H2A	116.9 (15)	N4—C13—H13	119.00
N1—N2—H2A	124.6 (15)	C15—C14—C19	120.1 (3)
N6—N5—C20	119.58 (19)	O3—C14—C15	117.3 (2)
N5—N6—C22	120.3 (2)	O3—C14—C19	122.6 (2)
C23—N7—C24	115.9 (2)	C14—C15—C16	121.5 (3)
C25—N8—C26	115.2 (2)	C15—C16—C17	119.8 (3)
C22—N6—H6	117 (2)	C16—C17—C18	119.7 (3)
N5—N6—H6	123 (2)	C17—C18—C19	122.0 (3)
O1—C1—C2	117.5 (2)	C18—C19—C20	120.9 (2)
C2—C1—C6	120.1 (2)	C14—C19—C18	116.9 (2)
O1—C1—C6	122.37 (19)	C14—C19—C20	122.2 (2)
C1—C2—C3	121.3 (2)	N5—C20—C21	123.2 (3)
C2—C3—C4	120.0 (3)	N5—C20—C19	116.0 (2)
C3—C4—C5	119.4 (2)	C19—C20—C21	120.8 (3)
C4—C5—C6	122.5 (2)	O4—C22—N6	124.0 (3)
C1—C6—C5	116.7 (2)	O4—C22—C23	123.9 (3)
C1—C6—C7	122.37 (18)	N6—C22—C23	112.0 (2)
C5—C6—C7	120.9 (2)	C22—C23—C26	120.6 (2)
N1—C7—C6	115.00 (18)	N7—C23—C22	117.8 (3)
C6—C7—C8	121.04 (18)	N7—C23—C26	121.6 (2)
N1—C7—C8	123.96 (19)	N7—C24—C25	122.0 (3)
O2—C9—N2	123.4 (2)	N8—C25—C24	122.9 (3)
O2—C9—C10	122.60 (19)	N8—C26—C23	122.4 (3)
N2—C9—C10	114.0 (2)	C14—C15—H15	119.00
N3—C10—C13	122.1 (2)	C16—C15—H15	119.00
C9—C10—C13	120.3 (2)	C15—C16—H16	120.00
N3—C10—C9	117.61 (18)	C17—C16—H16	120.00
N3—C11—C12	121.8 (3)	C16—C17—H17	120.00
N4—C12—C11	122.9 (3)	C18—C17—H17	120.00
N4—C13—C10	122.7 (2)	C17—C18—H18	119.00
C3—C2—H2	119.00	C19—C18—H18	119.00
C1—C2—H2	119.00	C20—C21—H21A	113 (3)
C2—C3—H3	120.00	C20—C21—H21B	111 (2)
C4—C3—H3	120.00	C20—C21—H21C	109 (2)
C3—C4—H4	120.00	H21A—C21—H21B	111 (4)
C5—C4—H4	120.00	H21A—C21—H21C	106 (4)
C4—C5—H5	119.00	H21B—C21—H21C	107 (4)
C6—C5—H5	119.00	N7—C24—H24	119.00
H8A—C8—H8B	110.00	C25—C24—H24	119.00
H8A—C8—H8C	109.00	N8—C25—H25	119.00
C7—C8—H8C	109.00	C24—C25—H25	119.00
C7—C8—H8B	109.00	N8—C26—H26	119.00
H8B—C8—H8C	110.00	C23—C26—H26	119.00
C7—N1—N2—C9	179.6 (2)	C1—C6—C7—N1	−7.5 (3)
N2—N1—C7—C6	−179.11 (18)	C1—C6—C7—C8	173.0 (2)
N2—N1—C7—C8	0.5 (3)	C5—C6—C7—C8	−8.5 (3)
N1—N2—C9—O2	0.2 (3)	N2—C9—C10—N3	4.2 (3)
N1—N2—C9—C10	179.11 (18)	N2—C9—C10—C13	−175.6 (2)
C11—N3—C10—C9	−178.49 (19)	O2—C9—C10—N3	−177.0 (2)
C11—N3—C10—C13	1.2 (3)	O2—C9—C10—C13	3.3 (3)
C10—N3—C11—C12	0.5 (3)	N3—C10—C13—N4	−2.5 (3)
C13—N4—C12—C11	0.0 (3)	C9—C10—C13—N4	177.2 (2)
C12—N4—C13—C10	1.8 (3)	N3—C11—C12—N4	−1.1 (4)
C20—N5—N6—C22	−178.8 (2)	O3—C14—C15—C16	−178.7 (3)
N6—N5—C20—C19	179.7 (2)	C19—C14—C15—C16	0.5 (4)
N6—N5—C20—C21	−0.7 (4)	O3—C14—C19—C18	178.5 (2)
N5—N6—C22—O4	−0.4 (4)	O3—C14—C19—C20	−1.3 (3)
N5—N6—C22—C23	179.8 (2)	C15—C14—C19—C18	−0.6 (3)
C24—N7—C23—C22	179.6 (2)	C15—C14—C19—C20	179.5 (2)
C24—N7—C23—C26	−0.6 (4)	C14—C15—C16—C17	−0.1 (4)
C23—N7—C24—C25	−0.7 (4)	C15—C16—C17—C18	−0.3 (4)
C26—N8—C25—C24	−0.5 (4)	C16—C17—C18—C19	0.1 (4)
C25—N8—C26—C23	−0.8 (4)	C17—C18—C19—C14	0.3 (4)
O1—C1—C6—C5	178.8 (2)	C17—C18—C19—C20	−179.8 (2)
O1—C1—C6—C7	−2.6 (3)	C14—C19—C20—N5	−2.1 (3)
C2—C1—C6—C7	177.9 (2)	C14—C19—C20—C21	178.2 (3)
O1—C1—C2—C3	179.5 (2)	C18—C19—C20—N5	178.1 (2)
C2—C1—C6—C5	−0.8 (3)	C18—C19—C20—C21	−1.7 (4)
C6—C1—C2—C3	−0.9 (3)	O4—C22—C23—N7	−177.6 (3)
C1—C2—C3—C4	1.2 (4)	O4—C22—C23—C26	2.6 (4)
C2—C3—C4—C5	0.3 (3)	N6—C22—C23—N7	2.2 (3)
C3—C4—C5—C6	−2.1 (3)	N6—C22—C23—C26	−177.6 (2)
C4—C5—C6—C7	−176.4 (2)	N7—C23—C26—N8	1.4 (4)
C4—C5—C6—C1	2.3 (3)	C22—C23—C26—N8	−178.8 (2)
C5—C6—C7—N1	171.1 (2)	N7—C24—C25—N8	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.537 (2)	145
N2—H2A···N3	0.80 (2)	2.26 (2)	2.654 (3)	111.5 (17)
O3—H3A···N5	0.82	1.82	2.534 (3)	145
N6—H6···N7	0.80 (3)	2.21 (3)	2.628 (3)	113 (3)
C3—H3···O3i	0.93	2.59	3.403 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.537 (2)	145
N2—H2A⋯N3	0.80 (2)	2.26 (2)	2.654 (3)	111.5 (17)
O3—H3A⋯N5	0.82	1.82	2.534 (3)	145
N6—H6⋯N7	0.80 (3)	2.21 (3)	2.628 (3)	113 (3)
C3—H3⋯O3i	0.93	2.59	3.403 (3)	146

Symmetry code: (i) .