(2E)-2-(4-Hy­droxy-3-meth­oxy­benzyl­idene)hydrazinecarboxamide

Tahir, M.N.; Ali, A.; Umar, M.N.; Hussain, I.; Shad, H.A.

doi:10.1107/S1600536812025299

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2071

https://doi.org/10.1107/S1600536812025299

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(2E)-2-(4-Hydroxy-3-methoxybenzylidene)hydrazinecarboxamide

M. Nawaz Tahir,^a ^* Akbar Ali,^b M. Naveed Umar,^b Ishtiaq Hussain ^c and Hazoor Ahmad Shad ^d

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Malakand, Pakistan, ^cDepartment of Chemistry, University of Sargodha, Pakistan, and ^dDepartment of Chemistry, Government Post Graduate College, Gojra, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 June 2012; accepted 4 June 2012; online 13 June 2012)

In the title compound, C₉H₁₁N₃O₃, two molecules are present in the asymmetric unit in which the 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide units are almost planar [with r.m.s. deviations 0.0212 and 0.0066 Å, respectively, in one molecule and 0.0346 and 0.0095 Å, respectively, in the other] and are oriented at dihedral angles of 9.7 (3) and 16.6 (3)°. In both molecules, two S(5) ring motifs are present due to N—H⋯N and O—H⋯O hydrogen bonds. In the crystal, the molecules are dimerized with each other due to pairs of N—H⋯O hydrogen bonds, forming an R₂²(8) ring motif. O—H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For a related structure, see: Tahir et al. (2012 ). For graph–set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₁₁N₃O₃
M_r = 209.21
Orthorhombic, P c a 2₁
a = 13.9945 (14) Å
b = 5.0440 (4) Å
c = 27.286 (2) Å
V = 1926.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.957, T_max = 0.966
8297 measured reflections
1931 independent reflections
1046 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.113
S = 0.98
1931 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	2.17	2.627 (6)	115
O2—H2A⋯O5ⁱ	0.82	2.34	3.108 (7)	156
N2—H2B⋯O6ⁱⁱ	0.86	2.11	2.923 (7)	158
N3—H3A⋯O6ⁱⁱⁱ	0.86	2.16	2.987 (7)	162
N3—H3B⋯N1	0.86	2.31	2.674 (8)	106
O5—H5A⋯O4	0.82	2.18	2.632 (6)	115
N5—H5B⋯O3^iv	0.86	2.08	2.909 (7)	161
N6—H6A⋯O3^v	0.86	2.13	2.965 (7)	164
N6—H6B⋯N4	0.86	2.32	2.677 (7)	105
Symmetry codes: (i) $[-x, -y, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x-{\script{1\over 2}}, -y, z]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+1, z]$ .

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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025299/bq2364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025299/bq2364Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025299/bq2364Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized as a derivative. Recently we have reported the crystal structure of (2E)-2-(3,4-dimethoxybenzylidene)hydrazinecarboxamide (Tahir et al., 2012) which is related to the title compound.

In (I), two molecules are present in the asymmetric unit, which differ slightly from each other geometrically. In one molecule, the parts of 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide A (C1—C8/O1/O2) and B (N1/N2/C9/N3/O3), are almost planar with r.m.s. deviations of 0.0212 Å and 0.0066 Å, respectively. The dihedral angle between A/B is 16.57 (26)°. In the second molecule, the similar groups C (C10—C17/O4/O5) and D (N4/N5/C18/N6/O6) are also planar with r.m.s. deviations of 0.0346 Å and 0.0095 Å, respectively, and the dihedral angle between C/D is 9.74 (28)°. In both molecules two S(5) ring motifs (Bernstein et al., 1995) are present due to H–bonding of N—H···N and O—H···O types (Table 1, Fig. 1). The molecules are dimerized with each other due to N—H···O type of H-bondings and form R₂²(8) ring motifs (Table 1, Fig. 2). The molecules are stabilized in the form of three-dimensional polymeric network.

Related literature top

For a related structure, see: Tahir et al. (2012). For graph–set notation, see: Bernstein et al. (1995).

Experimental top

Equimolar quantities of 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide were refluxed in methanol along with few drops of acetic acid as catalyst for 45 min resulting in light orange solution. The solution was kept at room temperature which afforded light orange needles after few days.

Structure description top

For a related structure, see: Tahir et al. (2012). For graph–set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form ring motifs in three-dimensional polymeric network.

(2E)-2-(4-Hydroxy-3-methoxybenzylidene)hydrazinecarboxamide top

Crystal data top

C₉H₁₁N₃O₃	F(000) = 880
M_r = 209.21	D_x = 1.443 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2704 reflections
a = 13.9945 (14) Å	θ = 1.8–26.0°
b = 5.0440 (4) Å	µ = 0.11 mm⁻¹
c = 27.286 (2) Å	T = 296 K
V = 1926.0 (3) Å³	Needle, colorless
Z = 8	0.30 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1931 independent reflections
Radiation source: fine-focus sealed tube	1046 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −3→6
T_min = 0.957, T_max = 0.966	l = −33→33
8297 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.039P)²] where P = (F_o² + 2F_c²)/3
1931 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₉H₁₁N₃O₃	V = 1926.0 (3) Å³
M_r = 209.21	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 13.9945 (14) Å	µ = 0.11 mm⁻¹
b = 5.0440 (4) Å	T = 296 K
c = 27.286 (2) Å	0.30 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1931 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1046 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.966	R_int = 0.081
8297 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.98	Δρ_max = 0.22 e Å⁻³
1931 reflections	Δρ_min = −0.25 e Å⁻³
275 parameters

Special details top

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 e.s.d.'s 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.

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

	x	y	z	U_iso*/U_eq
O1	0.1256 (3)	−0.4282 (10)	0.51673 (17)	0.051 (2)
O2	0.3120 (3)	−0.4570 (10)	0.52664 (17)	0.0437 (19)
O3	−0.0668 (3)	0.7125 (10)	0.3095 (2)	0.0423 (16)
N1	0.0730 (4)	0.3033 (11)	0.38554 (19)	0.035 (2)
N2	0.0463 (3)	0.5085 (12)	0.3552 (2)	0.041 (2)
N3	−0.1032 (4)	0.3268 (12)	0.3479 (2)	0.048 (2)
C1	0.1988 (4)	0.0965 (14)	0.4299 (2)	0.031 (3)
C2	0.1392 (5)	−0.0745 (13)	0.4553 (3)	0.035 (3)
C3	0.1765 (4)	−0.2580 (13)	0.4879 (2)	0.031 (3)
C4	0.2739 (5)	−0.2735 (12)	0.4950 (2)	0.031 (2)
C5	0.3343 (4)	−0.1063 (13)	0.4703 (2)	0.039 (3)
C6	0.2965 (4)	0.0792 (13)	0.4384 (2)	0.037 (3)
C7	0.0252 (4)	−0.4398 (15)	0.5100 (3)	0.049 (3)
C8	0.1602 (5)	0.2916 (13)	0.3966 (2)	0.032 (2)
C9	−0.0445 (4)	0.5255 (14)	0.3362 (2)	0.031 (2)
O4	−0.0199 (3)	0.9504 (9)	0.10503 (17)	0.0413 (16)
O5	−0.2032 (3)	0.8811 (10)	0.08760 (18)	0.049 (2)
O6	0.2021 (3)	−0.1888 (9)	0.31097 (17)	0.0430 (17)
N4	0.0595 (3)	0.2198 (10)	0.23612 (18)	0.0307 (17)
N5	0.0884 (4)	0.0189 (11)	0.2668 (2)	0.040 (2)
N6	0.2384 (4)	0.1926 (10)	0.2705 (2)	0.044 (2)
C10	−0.0733 (4)	0.4019 (13)	0.1914 (2)	0.031 (2)
C11	−0.0188 (4)	0.5961 (13)	0.1670 (2)	0.029 (2)
C12	−0.0626 (5)	0.7582 (13)	0.1326 (2)	0.030 (2)
C13	−0.1603 (4)	0.7257 (13)	0.1226 (2)	0.032 (3)
C14	−0.2137 (5)	0.5398 (14)	0.1471 (3)	0.038 (3)
C15	−0.1697 (4)	0.3796 (13)	0.1809 (2)	0.035 (2)
C16	0.0808 (4)	0.9841 (14)	0.1099 (3)	0.045 (3)
C17	−0.0297 (4)	0.2151 (12)	0.2254 (2)	0.030 (2)
C18	0.1785 (5)	0.0009 (15)	0.2845 (2)	0.033 (2)
H2	0.07352	−0.06591	0.45048	0.0424*
H2A	0.26884	−0.54591	0.53860	0.0649*
H2B	0.08747	0.62892	0.34795	0.0490*
H3A	−0.16059	0.32439	0.33656	0.0569*
H3B	−0.08372	0.20124	0.36668	0.0569*
H5	0.40001	−0.11747	0.47486	0.0464*
H6	0.33740	0.19515	0.42224	0.0444*
H7A	0.01136	−0.49086	0.47685	0.0593*
H7B	−0.00207	−0.26864	0.51642	0.0593*
H7C	−0.00159	−0.56760	0.53213	0.0593*
H8	0.20166	0.41433	0.38265	0.0377*
H5A	−0.16623	0.99847	0.07909	0.0729*
H5B	0.04750	−0.10020	0.27510	0.0479*
H6A	0.29709	0.18908	0.27988	0.0534*
H6B	0.21835	0.31947	0.25217	0.0534*
H11	0.04595	0.61546	0.17385	0.0351*
H14	−0.27877	0.52269	0.14088	0.0458*
H15	−0.20577	0.25249	0.19730	0.0421*
H16A	0.11246	0.81983	0.10266	0.0675*
H16B	0.09561	1.03701	0.14284	0.0675*
H16C	0.10226	1.11826	0.08749	0.0675*
H17	−0.06819	0.08711	0.23996	0.0368*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.028 (3)	0.070 (4)	0.055 (4)	−0.003 (3)	−0.004 (3)	0.032 (3)
O2	0.030 (3)	0.052 (4)	0.049 (3)	0.005 (2)	−0.003 (2)	0.013 (3)
O3	0.028 (2)	0.039 (3)	0.060 (3)	0.000 (2)	−0.011 (2)	0.016 (3)
N1	0.031 (3)	0.031 (4)	0.042 (4)	0.001 (3)	−0.010 (3)	0.012 (3)
N2	0.024 (3)	0.036 (4)	0.062 (4)	−0.005 (3)	−0.013 (3)	0.013 (3)
N3	0.026 (3)	0.055 (5)	0.062 (4)	−0.003 (3)	−0.010 (3)	0.020 (4)
C1	0.025 (4)	0.038 (5)	0.030 (4)	0.000 (3)	0.001 (3)	0.005 (3)
C2	0.029 (4)	0.037 (5)	0.040 (4)	0.007 (4)	−0.007 (3)	0.001 (4)
C3	0.029 (4)	0.039 (5)	0.026 (4)	0.000 (3)	0.003 (3)	0.003 (3)
C4	0.036 (4)	0.033 (4)	0.023 (4)	0.010 (4)	−0.005 (3)	−0.002 (3)
C5	0.024 (4)	0.039 (5)	0.054 (5)	0.001 (3)	−0.004 (3)	0.007 (4)
C6	0.029 (4)	0.033 (5)	0.049 (5)	−0.002 (3)	0.003 (3)	0.007 (4)
C7	0.027 (4)	0.074 (6)	0.047 (5)	−0.009 (4)	−0.003 (4)	0.006 (4)
C8	0.033 (4)	0.032 (4)	0.030 (4)	−0.005 (4)	0.003 (3)	0.000 (3)
C9	0.023 (4)	0.032 (4)	0.038 (4)	0.001 (3)	0.002 (3)	−0.005 (4)
O4	0.026 (2)	0.045 (3)	0.053 (3)	0.002 (2)	0.004 (2)	0.018 (3)
O5	0.036 (3)	0.056 (4)	0.054 (4)	0.008 (3)	−0.008 (3)	0.023 (3)
O6	0.037 (3)	0.037 (3)	0.055 (3)	0.006 (2)	−0.013 (3)	0.016 (3)
N4	0.033 (3)	0.032 (3)	0.027 (3)	0.001 (3)	−0.003 (2)	0.008 (3)
N5	0.037 (3)	0.035 (4)	0.048 (4)	−0.008 (3)	−0.009 (3)	0.019 (3)
N6	0.028 (3)	0.041 (4)	0.064 (5)	−0.004 (3)	−0.007 (3)	0.011 (3)
C10	0.035 (4)	0.033 (4)	0.024 (4)	−0.001 (4)	−0.006 (3)	−0.004 (3)
C11	0.023 (3)	0.038 (4)	0.027 (4)	−0.001 (3)	−0.003 (3)	−0.001 (4)
C12	0.031 (4)	0.025 (4)	0.035 (4)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C13	0.029 (4)	0.040 (5)	0.027 (4)	0.006 (4)	−0.002 (3)	0.005 (4)
C14	0.022 (3)	0.050 (5)	0.043 (5)	0.000 (4)	−0.005 (3)	−0.001 (4)
C15	0.026 (3)	0.039 (4)	0.041 (4)	−0.006 (4)	0.001 (3)	0.012 (4)
C16	0.027 (4)	0.052 (5)	0.056 (6)	−0.008 (4)	0.000 (4)	0.005 (4)
C17	0.027 (4)	0.031 (4)	0.033 (4)	0.004 (3)	−0.007 (3)	0.004 (3)
C18	0.030 (4)	0.032 (4)	0.038 (4)	−0.004 (4)	−0.002 (3)	−0.005 (4)

Geometric parameters (Å, º) top

O1—C3	1.365 (8)	C1—C8	1.444 (9)
O1—C7	1.418 (7)	C2—C3	1.386 (9)
O2—C4	1.373 (8)	C3—C4	1.379 (9)
O3—C9	1.232 (8)	C4—C5	1.371 (9)
O2—H2A	0.8200	C5—C6	1.383 (8)
O4—C12	1.365 (8)	C2—H2	0.9300
O4—C16	1.426 (7)	C5—H5	0.9300
O5—C13	1.374 (8)	C6—H6	0.9300
O6—C18	1.244 (8)	C7—H7C	0.9600
O5—H5A	0.8200	C7—H7A	0.9600
N1—C8	1.259 (9)	C7—H7B	0.9600
N1—N2	1.377 (8)	C8—H8	0.9300
N2—C9	1.375 (7)	C10—C11	1.409 (9)
N3—C9	1.335 (9)	C10—C15	1.384 (8)
N2—H2B	0.8600	C10—C17	1.456 (8)
N3—H3B	0.8600	C11—C12	1.388 (9)
N3—H3A	0.8600	C12—C13	1.404 (9)
N4—N5	1.375 (7)	C13—C14	1.373 (9)
N4—C17	1.282 (7)	C14—C15	1.372 (10)
N5—C18	1.353 (9)	C11—H11	0.9300
N6—C18	1.336 (9)	C14—H14	0.9300
N5—H5B	0.8600	C15—H15	0.9300
N6—H6B	0.8600	C16—H16A	0.9600
N6—H6A	0.8600	C16—H16B	0.9600
C1—C2	1.386 (9)	C16—H16C	0.9600
C1—C6	1.390 (8)	C17—H17	0.9300

C3—O1—C7	117.9 (5)	C5—C6—H6	119.00
C4—O2—H2A	109.00	H7A—C7—H7C	109.00
C12—O4—C16	117.8 (5)	H7A—C7—H7B	109.00
C13—O5—H5A	109.00	O1—C7—H7B	109.00
N2—N1—C8	116.3 (5)	O1—C7—H7C	109.00
N1—N2—C9	121.6 (5)	O1—C7—H7A	109.00
C9—N2—H2B	119.00	H7B—C7—H7C	110.00
N1—N2—H2B	119.00	C1—C8—H8	119.00
C9—N3—H3A	120.00	N1—C8—H8	118.00
H3A—N3—H3B	120.00	C11—C10—C15	119.1 (5)
C9—N3—H3B	120.00	C15—C10—C17	119.2 (5)
N5—N4—C17	114.3 (5)	C11—C10—C17	121.6 (5)
N4—N5—C18	122.7 (5)	C10—C11—C12	119.4 (5)
C18—N5—H5B	119.00	C11—C12—C13	119.5 (6)
N4—N5—H5B	119.00	O4—C12—C11	126.7 (6)
H6A—N6—H6B	120.00	O4—C12—C13	113.7 (5)
C18—N6—H6A	120.00	O5—C13—C14	119.4 (5)
C18—N6—H6B	120.00	O5—C13—C12	119.6 (5)
C2—C1—C6	118.0 (6)	C12—C13—C14	121.0 (6)
C2—C1—C8	120.9 (6)	C13—C14—C15	119.0 (6)
C6—C1—C8	121.1 (6)	C10—C15—C14	121.9 (6)
C1—C2—C3	120.7 (6)	N4—C17—C10	122.8 (5)
O1—C3—C2	126.4 (5)	N5—C18—N6	115.7 (6)
C2—C3—C4	120.0 (6)	O6—C18—N5	120.4 (6)
O1—C3—C4	113.5 (5)	O6—C18—N6	123.8 (6)
O2—C4—C5	119.0 (6)	C10—C11—H11	120.00
O2—C4—C3	120.7 (6)	C12—C11—H11	120.00
C3—C4—C5	120.4 (6)	C13—C14—H14	120.00
C4—C5—C6	119.3 (5)	C15—C14—H14	120.00
C1—C6—C5	121.6 (6)	C10—C15—H15	119.00
N1—C8—C1	123.1 (6)	C14—C15—H15	119.00
O3—C9—N2	120.3 (6)	O4—C16—H16A	110.00
N2—C9—N3	115.6 (6)	O4—C16—H16B	109.00
O3—C9—N3	124.1 (5)	O4—C16—H16C	110.00
C3—C2—H2	120.00	H16A—C16—H16B	109.00
C1—C2—H2	120.00	H16A—C16—H16C	109.00
C6—C5—H5	120.00	H16B—C16—H16C	109.00
C4—C5—H5	120.00	N4—C17—H17	119.00
C1—C6—H6	119.00	C10—C17—H17	119.00

C7—O1—C3—C2	6.5 (9)	O1—C3—C4—O2	3.3 (8)
C7—O1—C3—C4	−176.1 (6)	O1—C3—C4—C5	−177.0 (5)
C16—O4—C12—C11	2.9 (9)	C2—C3—C4—C5	0.6 (9)
C16—O4—C12—C13	−175.3 (6)	C3—C4—C5—C6	0.4 (9)
C8—N1—N2—C9	172.7 (6)	O2—C4—C5—C6	−180.0 (5)
N2—N1—C8—C1	176.9 (5)	C4—C5—C6—C1	−1.5 (9)
N1—N2—C9—N3	−2.0 (8)	C15—C10—C11—C12	−0.8 (9)
N1—N2—C9—O3	179.3 (6)	C17—C10—C11—C12	175.9 (6)
C17—N4—N5—C18	−175.8 (6)	C11—C10—C15—C14	0.5 (9)
N5—N4—C17—C10	−176.6 (5)	C17—C10—C15—C14	−176.2 (6)
N4—N5—C18—O6	−177.8 (5)	C11—C10—C17—N4	1.8 (9)
N4—N5—C18—N6	0.3 (9)	C15—C10—C17—N4	178.5 (6)
C6—C1—C8—N1	175.4 (6)	C10—C11—C12—O4	−178.3 (6)
C2—C1—C6—C5	1.5 (9)	C10—C11—C12—C13	−0.2 (9)
C6—C1—C2—C3	−0.4 (10)	O4—C12—C13—O5	0.2 (8)
C8—C1—C2—C3	−178.8 (6)	O4—C12—C13—C14	179.8 (6)
C8—C1—C6—C5	179.8 (6)	C11—C12—C13—O5	−178.2 (5)
C2—C1—C8—N1	−6.3 (10)	C11—C12—C13—C14	1.4 (9)
C1—C2—C3—C4	−0.6 (10)	O5—C13—C14—C15	178.0 (6)
C1—C2—C3—O1	176.7 (6)	C12—C13—C14—C15	−1.7 (10)
C2—C3—C4—O2	−179.0 (6)	C13—C14—C15—C10	0.7 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	2.17	2.627 (6)	115
O2—H2A···O5ⁱ	0.82	2.34	3.108 (7)	156
N2—H2B···O6ⁱⁱ	0.86	2.11	2.923 (7)	158
N3—H3A···O6ⁱⁱⁱ	0.86	2.16	2.987 (7)	162
N3—H3B···N1	0.86	2.31	2.674 (8)	106
O5—H5A···O4	0.82	2.18	2.632 (6)	115
N5—H5B···O3^iv	0.86	2.08	2.909 (7)	161
N6—H6A···O3^v	0.86	2.13	2.965 (7)	164
N6—H6B···N4	0.86	2.32	2.677 (7)	105

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

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₃O₃
M_r	209.21
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	13.9945 (14), 5.0440 (4), 27.286 (2)
V (Å³)	1926.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	8297, 1931, 1046
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.113, 0.98
No. of reflections	1931
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	2.17	2.627 (6)	115
O2—H2A···O5ⁱ	0.82	2.34	3.108 (7)	156
N2—H2B···O6ⁱⁱ	0.86	2.11	2.923 (7)	158
N3—H3A···O6ⁱⁱⁱ	0.86	2.16	2.987 (7)	162
N3—H3B···N1	0.86	2.31	2.674 (8)	106
O5—H5A···O4	0.82	2.18	2.632 (6)	115
N5—H5B···O3^iv	0.86	2.08	2.909 (7)	161
N6—H6A···O3^v	0.86	2.13	2.965 (7)	164
N6—H6B···N4	0.86	2.32	2.677 (7)	105

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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