(E)-N′-(1,3-Benzodioxol-5-ylmethyl­ene)isonicotinohydrazide

Yin, Z.; Qian, H.; Yu-li, F.; Yu-zhen, C.

doi:10.1107/S1600536807044881

(E)-N′-(1,3-Benzodioxol-5-ylmethylene)isonicotinohydrazide

Z. Yin, H. Qian, F. Yu-li and C. Yu-zhen

The asymmetric unit of the title compound, C₁₄H₁₁N₃O₃, contains two similar molecules. Each molecule is almost planar; the dihedral angles between the pyridine ring and the benzene ring are 5.78 (15) and 8.24 (15)°. The crystal structure involves intermolecular N—H

N and C—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044881/xu2324sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044881/xu2324Isup2.hkl Contains datablock I

CCDC reference: 663801

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.083
wR factor = 0.165
Data-to-parameter ratio = 13.5

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No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecular structure is shown in Fig. 1. Each molecule is almost coplanar, making the dihedral angle of 5.78 (15) and 8.24 (15)° between pyridine and benzene rings, respectively. Bond lengths and bond angles agree with the isonicotinohydrazide derivatives (Qian et al., 2006).

In the crystal structure, there are intermolecular N—H···N and C—H···N hydrogen bonding (Table 1), which helps to stabilize the crystal structure (Fig. 2).

Related literature top

For general background, see: Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Qian et al. (2006).

Experimental top

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous methanol (15 ml), then H₂SO₄ solution (98% 0.5 ml) was added to the above solution. The mixture was stirred for several minutes at 351 K, furylideneacetone (1 mmol 0.136 g) in methanol (8 ml) was added dropwise and the mixture was refluxed for 2 h. The solid product was isolated and recrystallized in dichloromethane, brown single crystals of the title compound were obtained after 1 d.

Structure description top

In the crystal structure, there are intermolecular N—H···N and C—H···N hydrogen bonding (Table 1), which helps to stabilize the crystal structure (Fig. 2).

For general background, see: Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Qian et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

	Fig. 1. The molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of (I), showing the intermolecular hydrogen bonds as dashed lines.

(E)-N'-(1,3-benzodioxol-5-ylmethylene)isonicotinohydrazide top

Crystal data top

C₁₄H₁₁N₃O₃	Z = 4
M_r = 269.26	F(000) = 560
Triclinic, P1	D_x = 1.462 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9190 (16) Å	Cell parameters from 1205 reflections
b = 10.955 (2) Å	θ = 2.5–23.5°
c = 15.479 (3) Å	µ = 0.11 mm⁻¹
α = 78.88 (3)°	T = 298 K
β = 80.11 (3)°	Block, brown
γ = 69.08 (3)°	0.27 × 0.23 × 0.20 mm
V = 1223.0 (5) Å³

Data collection top

Bruker SMART CCD area detector diffractometer	3998 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 26.5°, θ_min = 2.6°
φ and ω scans	h = −9→9
13621 measured reflections	k = −13→13
4961 independent reflections	l = −19→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.042P)² + 1.0203P] where P = (F_o² + 2F_c²)/3
4961 reflections	(Δ/σ)_max < 0.001
367 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₃	γ = 69.08 (3)°
M_r = 269.26	V = 1223.0 (5) Å³
Triclinic, P1	Z = 4
a = 7.9190 (16) Å	Mo Kα radiation
b = 10.955 (2) Å	µ = 0.11 mm⁻¹
c = 15.479 (3) Å	T = 298 K
α = 78.88 (3)°	0.27 × 0.23 × 0.20 mm
β = 80.11 (3)°

Data collection top

Bruker SMART CCD area detector diffractometer	3998 reflections with I > 2σ(I)
13621 measured reflections	R_int = 0.051
4961 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	2 restraints
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.21 e Å⁻³
4961 reflections	Δρ_min = −0.24 e Å⁻³
367 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.9146 (4)	−0.2658 (2)	0.53135 (14)	0.0643 (8)
O2	0.3782 (3)	0.4409 (2)	0.74818 (15)	0.0521 (6)
O3	0.6028 (4)	0.2414 (2)	0.78416 (14)	0.0580 (7)
O4	0.8014 (3)	0.7100 (2)	0.02373 (13)	0.0481 (6)
O5	0.4833 (4)	0.0337 (2)	0.23747 (15)	0.0570 (7)
O6	0.4886 (3)	0.2214 (2)	0.28232 (14)	0.0517 (6)
N1	1.0747 (4)	−0.4254 (2)	0.23574 (16)	0.0423 (6)
N2	0.8450 (4)	−0.0721 (2)	0.43657 (15)	0.0383 (6)
N3	0.7771 (4)	0.0014 (2)	0.50607 (15)	0.0390 (6)
N4	1.0389 (4)	0.9103 (2)	−0.26796 (16)	0.0401 (6)
N5	0.8220 (3)	0.5591 (2)	−0.06345 (15)	0.0335 (6)
N6	0.7515 (3)	0.4833 (2)	0.00541 (15)	0.0339 (6)
C1	0.9666 (4)	−0.2782 (3)	0.37672 (18)	0.0329 (6)
C2	0.8959 (4)	−0.2270 (3)	0.29636 (19)	0.0376 (7)
H2	0.8112	−0.1425	0.2880	0.045*
C3	0.9532 (5)	−0.3036 (3)	0.2290 (2)	0.0431 (8)
H3	0.9042	−0.2683	0.1755	0.052*
C4	1.1388 (5)	−0.4734 (3)	0.3139 (2)	0.0499 (9)
H4	1.2223	−0.5586	0.3206	0.060*
C5	1.0899 (5)	−0.4056 (3)	0.3856 (2)	0.0431 (8)
H5	1.1387	−0.4445	0.4388	0.052*
C6	0.9083 (5)	−0.2058 (3)	0.45675 (19)	0.0401 (7)
C7	0.6917 (4)	0.1225 (3)	0.48411 (19)	0.0368 (7)
H7	0.6809	0.1557	0.4246	0.044*
C8	0.6098 (4)	0.2110 (3)	0.55047 (18)	0.0335 (6)
C9	0.6627 (4)	0.1724 (3)	0.63659 (19)	0.0358 (7)
H9	0.7533	0.0927	0.6519	0.043*
C10	0.5752 (4)	0.2570 (3)	0.69660 (18)	0.0355 (7)
C11	0.4418 (4)	0.3763 (3)	0.67524 (19)	0.0356 (7)
C12	0.3882 (4)	0.4171 (3)	0.5921 (2)	0.0452 (8)
H12	0.2982	0.4976	0.5778	0.054*
C13	0.4758 (5)	0.3312 (3)	0.5298 (2)	0.0442 (8)
H13	0.4432	0.3557	0.4725	0.053*
C14	0.4804 (5)	0.3570 (4)	0.8169 (2)	0.0547 (9)
H14A	0.5475	0.4025	0.8375	0.066*
H14B	0.3991	0.3337	0.8665	0.066*
C15	0.9117 (4)	0.7499 (3)	−0.12767 (17)	0.0295 (6)
C16	0.9048 (4)	0.8749 (3)	−0.1192 (2)	0.0423 (8)
H16	0.8573	0.9079	−0.0659	0.051*
C17	0.9683 (5)	0.9503 (3)	−0.1899 (2)	0.0459 (8)
H17	0.9614	1.0343	−0.1826	0.055*
C18	1.0451 (5)	0.7897 (3)	−0.2758 (2)	0.0474 (8)
H18	1.0924	0.7595	−0.3300	0.057*
C19	0.9858 (5)	0.7067 (3)	−0.2083 (2)	0.0420 (8)
H19	0.9956	0.6227	−0.2171	0.050*
C20	0.8403 (4)	0.6714 (3)	−0.04863 (18)	0.0322 (6)
C21	0.7445 (4)	0.3777 (3)	−0.01433 (19)	0.0362 (7)
H21	0.7852	0.3584	−0.0718	0.043*
C22	0.6747 (4)	0.2859 (3)	0.05016 (18)	0.0321 (6)
C23	0.6145 (4)	0.3105 (3)	0.13782 (19)	0.0353 (7)
H23	0.6173	0.3852	0.1568	0.042*
C24	0.5518 (4)	0.2200 (3)	0.19372 (18)	0.0343 (6)
C25	0.5485 (4)	0.1076 (3)	0.1676 (2)	0.0390 (7)
C26	0.6067 (5)	0.0804 (3)	0.0828 (2)	0.0475 (8)
H26	0.6050	0.0044	0.0652	0.057*
C27	0.6692 (5)	0.1734 (3)	0.0240 (2)	0.0443 (8)
H27	0.7082	0.1593	−0.0346	0.053*
C28	0.4366 (5)	0.1062 (3)	0.3101 (2)	0.0500 (9)
H28A	0.4996	0.0525	0.3601	0.060*
H28B	0.3067	0.1315	0.3283	0.060*
H5A	0.857 (5)	0.529 (4)	−0.1163 (14)	0.080*
H2A	0.865 (5)	−0.033 (4)	0.3811 (12)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.116 (2)	0.0410 (13)	0.0273 (12)	−0.0198 (14)	−0.0016 (13)	−0.0022 (10)
O2	0.0592 (15)	0.0428 (13)	0.0477 (13)	−0.0028 (11)	−0.0015 (11)	−0.0227 (11)
O3	0.0806 (18)	0.0473 (14)	0.0341 (12)	−0.0005 (13)	−0.0090 (12)	−0.0162 (10)
O4	0.0675 (16)	0.0477 (13)	0.0318 (11)	−0.0272 (12)	0.0101 (11)	−0.0108 (10)
O5	0.0817 (18)	0.0492 (14)	0.0454 (14)	−0.0393 (14)	0.0014 (13)	0.0073 (11)
O6	0.0680 (16)	0.0471 (13)	0.0353 (12)	−0.0234 (12)	0.0152 (11)	−0.0056 (10)
N1	0.0583 (17)	0.0368 (14)	0.0342 (14)	−0.0194 (13)	0.0041 (12)	−0.0126 (11)
N2	0.0561 (16)	0.0324 (13)	0.0263 (12)	−0.0163 (12)	0.0053 (12)	−0.0094 (10)
N3	0.0533 (16)	0.0356 (14)	0.0284 (13)	−0.0173 (12)	0.0070 (11)	−0.0109 (11)
N4	0.0465 (15)	0.0399 (15)	0.0335 (14)	−0.0190 (12)	−0.0039 (12)	0.0038 (11)
N5	0.0407 (14)	0.0348 (13)	0.0263 (12)	−0.0192 (11)	0.0036 (11)	−0.0009 (10)
N6	0.0358 (13)	0.0324 (13)	0.0316 (13)	−0.0152 (11)	0.0005 (10)	0.0035 (10)
C1	0.0399 (16)	0.0302 (15)	0.0304 (15)	−0.0151 (12)	0.0003 (12)	−0.0056 (11)
C2	0.0463 (18)	0.0320 (15)	0.0316 (15)	−0.0100 (13)	−0.0029 (13)	−0.0051 (12)
C3	0.063 (2)	0.0418 (18)	0.0301 (16)	−0.0230 (16)	−0.0049 (14)	−0.0064 (13)
C4	0.063 (2)	0.0363 (17)	0.0462 (19)	−0.0102 (16)	−0.0023 (17)	−0.0117 (15)
C5	0.057 (2)	0.0357 (16)	0.0332 (16)	−0.0083 (15)	−0.0099 (14)	−0.0074 (13)
C6	0.058 (2)	0.0361 (16)	0.0279 (15)	−0.0182 (15)	0.0004 (14)	−0.0086 (12)
C7	0.0475 (18)	0.0387 (17)	0.0282 (15)	−0.0219 (14)	0.0045 (13)	−0.0073 (12)
C8	0.0426 (17)	0.0315 (15)	0.0299 (15)	−0.0184 (13)	0.0012 (12)	−0.0054 (12)
C9	0.0403 (16)	0.0266 (14)	0.0360 (16)	−0.0076 (12)	−0.0011 (13)	−0.0042 (12)
C10	0.0434 (17)	0.0357 (16)	0.0288 (14)	−0.0151 (13)	−0.0026 (13)	−0.0060 (12)
C11	0.0361 (16)	0.0336 (15)	0.0372 (16)	−0.0104 (13)	0.0019 (13)	−0.0132 (13)
C12	0.0479 (19)	0.0327 (16)	0.0478 (19)	−0.0019 (14)	−0.0096 (15)	−0.0073 (14)
C13	0.055 (2)	0.0407 (18)	0.0356 (17)	−0.0134 (15)	−0.0087 (15)	−0.0039 (14)
C14	0.059 (2)	0.056 (2)	0.044 (2)	−0.0083 (18)	−0.0002 (17)	−0.0221 (17)
C15	0.0278 (14)	0.0290 (14)	0.0286 (14)	−0.0072 (11)	−0.0035 (11)	−0.0010 (11)
C16	0.0530 (19)	0.0302 (16)	0.0388 (17)	−0.0126 (14)	0.0059 (14)	−0.0058 (13)
C17	0.054 (2)	0.0299 (16)	0.0491 (19)	−0.0154 (15)	0.0047 (16)	−0.0024 (14)
C18	0.063 (2)	0.056 (2)	0.0301 (16)	−0.0323 (18)	0.0055 (15)	−0.0100 (14)
C19	0.060 (2)	0.0407 (17)	0.0341 (16)	−0.0300 (16)	0.0053 (14)	−0.0105 (13)
C20	0.0288 (14)	0.0342 (15)	0.0298 (15)	−0.0072 (12)	−0.0016 (11)	−0.0036 (12)
C21	0.0402 (17)	0.0407 (17)	0.0276 (15)	−0.0161 (14)	−0.0034 (12)	−0.0003 (12)
C22	0.0334 (15)	0.0318 (15)	0.0300 (14)	−0.0114 (12)	−0.0054 (12)	0.0003 (11)
C23	0.0351 (16)	0.0281 (15)	0.0408 (17)	−0.0093 (12)	−0.0029 (13)	−0.0042 (12)
C24	0.0330 (15)	0.0348 (15)	0.0306 (15)	−0.0101 (12)	0.0004 (12)	−0.0001 (12)
C25	0.0420 (17)	0.0367 (16)	0.0385 (16)	−0.0188 (14)	−0.0053 (13)	0.0052 (13)
C26	0.069 (2)	0.0431 (19)	0.0409 (18)	−0.0310 (17)	−0.0065 (16)	−0.0061 (14)
C27	0.060 (2)	0.0452 (18)	0.0333 (16)	−0.0257 (16)	0.0005 (15)	−0.0081 (14)
C28	0.049 (2)	0.055 (2)	0.0440 (19)	−0.0255 (17)	0.0013 (15)	0.0072 (16)

Geometric parameters (Å, º) top

O1—C6	1.213 (4)	C8—C13	1.385 (4)
O2—C11	1.374 (3)	C8—C9	1.407 (4)
O2—C14	1.421 (4)	C9—C10	1.361 (4)
O3—C10	1.378 (3)	C9—H9	0.9300
O3—C14	1.415 (4)	C10—C11	1.379 (4)
O4—C20	1.224 (3)	C11—C12	1.366 (4)
O5—C25	1.364 (3)	C12—C13	1.396 (4)
O5—C28	1.423 (4)	C12—H12	0.9300
O6—C24	1.378 (3)	C13—H13	0.9300
O6—C28	1.431 (4)	C14—H14A	0.9700
N1—C4	1.332 (4)	C14—H14B	0.9700
N1—C3	1.334 (4)	C15—C19	1.380 (4)
N2—C6	1.358 (4)	C15—C16	1.382 (4)
N2—N3	1.386 (3)	C15—C20	1.503 (4)
N2—H2A	0.90 (2)	C16—C17	1.376 (4)
N3—C7	1.264 (4)	C16—H16	0.9300
N4—C17	1.327 (4)	C17—H17	0.9300
N4—C18	1.333 (4)	C18—C19	1.382 (4)
N5—C20	1.354 (4)	C18—H18	0.9300
N5—N6	1.387 (3)	C19—H19	0.9300
N5—H5A	0.90 (3)	C21—C22	1.460 (4)
N6—C21	1.274 (4)	C21—H21	0.9300
C1—C5	1.386 (4)	C22—C27	1.386 (4)
C1—C2	1.386 (4)	C22—C23	1.403 (4)
C1—C6	1.516 (4)	C23—C24	1.361 (4)
C2—C3	1.379 (4)	C23—H23	0.9300
C2—H2	0.9300	C24—C25	1.378 (4)
C3—H3	0.9300	C25—C26	1.367 (4)
C4—C5	1.377 (4)	C26—C27	1.400 (4)
C4—H4	0.9300	C26—H26	0.9300
C5—H5	0.9300	C27—H27	0.9300
C7—C8	1.457 (4)	C28—H28A	0.9700
C7—H7	0.9300	C28—H28B	0.9700

C11—O2—C14	105.5 (2)	C12—C13—H13	118.8
C10—O3—C14	105.6 (2)	O3—C14—O2	109.2 (3)
C25—O5—C28	106.3 (2)	O3—C14—H14A	109.8
C24—O6—C28	105.7 (2)	O2—C14—H14A	109.8
C4—N1—C3	116.1 (3)	O3—C14—H14B	109.8
C6—N2—N3	117.8 (2)	O2—C14—H14B	109.8
C6—N2—H2A	121 (3)	H14A—C14—H14B	108.3
N3—N2—H2A	121 (3)	C19—C15—C16	117.0 (3)
C7—N3—N2	115.2 (2)	C19—C15—C20	125.2 (3)
C17—N4—C18	116.1 (3)	C16—C15—C20	117.8 (3)
C20—N5—N6	119.5 (2)	C17—C16—C15	119.7 (3)
C20—N5—H5A	123 (3)	C17—C16—H16	120.1
N6—N5—H5A	118 (3)	C15—C16—H16	120.1
C21—N6—N5	114.9 (2)	N4—C17—C16	123.9 (3)
C5—C1—C2	117.8 (3)	N4—C17—H17	118.0
C5—C1—C6	118.4 (3)	C16—C17—H17	118.0
C2—C1—C6	123.7 (3)	N4—C18—C19	124.0 (3)
C3—C2—C1	118.9 (3)	N4—C18—H18	118.0
C3—C2—H2	120.5	C19—C18—H18	118.0
C1—C2—H2	120.5	C15—C19—C18	119.2 (3)
N1—C3—C2	124.0 (3)	C15—C19—H19	120.4
N1—C3—H3	118.0	C18—C19—H19	120.4
C2—C3—H3	118.0	O4—C20—N5	123.7 (3)
N1—C4—C5	124.5 (3)	O4—C20—C15	120.4 (3)
N1—C4—H4	117.7	N5—C20—C15	116.0 (2)
C5—C4—H4	117.7	N6—C21—C22	122.3 (3)
C4—C5—C1	118.6 (3)	N6—C21—H21	118.9
C4—C5—H5	120.7	C22—C21—H21	118.9
C1—C5—H5	120.7	C27—C22—C23	120.1 (3)
O1—C6—N2	124.8 (3)	C27—C22—C21	119.3 (3)
O1—C6—C1	121.0 (3)	C23—C22—C21	120.6 (3)
N2—C6—C1	114.2 (2)	C24—C23—C22	116.9 (3)
N3—C7—C8	121.1 (3)	C24—C23—H23	121.6
N3—C7—H7	119.4	C22—C23—H23	121.6
C8—C7—H7	119.4	C23—C24—C25	122.8 (3)
C13—C8—C9	119.9 (3)	C23—C24—O6	127.6 (3)
C13—C8—C7	120.2 (3)	C25—C24—O6	109.7 (2)
C9—C8—C7	119.9 (3)	O5—C25—C26	128.1 (3)
C10—C9—C8	117.0 (3)	O5—C25—C24	110.1 (3)
C10—C9—H9	121.5	C26—C25—C24	121.8 (3)
C8—C9—H9	121.5	C25—C26—C27	116.2 (3)
C9—C10—O3	127.8 (3)	C25—C26—H26	121.9
C9—C10—C11	122.5 (3)	C27—C26—H26	121.9
O3—C10—C11	109.7 (3)	C22—C27—C26	122.2 (3)
C12—C11—O2	128.2 (3)	C22—C27—H27	118.9
C12—C11—C10	121.9 (3)	C26—C27—H27	118.9
O2—C11—C10	109.9 (3)	O5—C28—O6	108.0 (2)
C11—C12—C13	116.3 (3)	O5—C28—H28A	110.1
C11—C12—H12	121.8	O6—C28—H28A	110.1
C13—C12—H12	121.8	O5—C28—H28B	110.1
C8—C13—C12	122.3 (3)	O6—C28—H28B	110.1
C8—C13—H13	118.8	H28A—C28—H28B	108.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱ	0.90 (2)	2.20 (3)	3.058 (4)	161 (3)
N5—H5A···N1ⁱⁱ	0.90 (3)	2.24 (3)	3.135 (3)	170 (4)
C19—H19···N1ⁱⁱ	0.93	2.49	3.396 (4)	164

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₃
M_r	269.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9190 (16), 10.955 (2), 15.479 (3)
α, β, γ (°)	78.88 (3), 80.11 (3), 69.08 (3)
V (Å³)	1223.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13621, 4961, 3998
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.165, 1.17
No. of reflections	4961
No. of parameters	367
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL (Bruker, 1998).