N-(2,5-Dimeth­oxy­phen­yl)-6-nitro­quinazolin-4-amine

Saad, S.M.; Khan, I.; Perveen, S.; Khan, K.M.; Yousuf, S.

doi:10.1107/S1600536812048878

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o8

https://doi.org/10.1107/S1600536812048878

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N-(2,5-Dimethoxyphenyl)-6-nitroquinazolin-4-amine

Syed Muhammad Saad,^a Imran Khan,^b Shahnaz Perveen,^b Khalid M. Khan ^a and Sammer Yousuf ^a ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bPCSIR Labortories Complex, Karachi, Shahrah-e-Dr. Salmuzzaman Siddiqui, Karachi 75280, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 21 November 2012; accepted 28 November 2012; online 5 December 2012)

In the title molecule, C₁₆H₁₄N₄O₄, the quinazoline ring is substantially planar (r.m.s. deviation = 0.0129 Å) and forms a dihedral angle of 2.73 (8)° with the benzene ring. The conformation of the molecule is stabilized by an intramolecular C—H⋯N hydrogen bond. In the crystal, molecules are linked into chains running parallel to the b axis by C—H⋯O hydrogen bonds. In addition, π–π stacking is observed between dimethoxy-substituted and nitro-substituted benzene rings, with centroid–centroid distances in the range 3.6438 (10)–3.7148 (10) Å.

Related literature

For the biological activity of quinazoline derivatives, see: Arfan et al. (2008 ); Sheng-Li et al. (2005 ); Kung et al. (1999 ); Ram et al. (1990 ); Misra et al. (1981 ); Hess et al. (1968 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄N₄O₄
M_r = 326.31
Triclinic, $[P \overline 1]$
a = 7.2440 (7) Å
b = 10.2832 (10) Å
c = 11.1622 (11) Å
α = 72.475 (2)°
β = 83.663 (2)°
γ = 70.429 (2)°
V = 747.05 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.29 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.970, T_max = 0.984
8510 measured reflections
2792 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.05
2792 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N2	0.93	2.22	2.833 (2)	123
C8—H8A⋯O3ⁱ	0.93	2.60	3.490 (2)	161
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812048878/rz5029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048878/rz5029Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812048878/rz5029Isup3.cml

checkCIF report

Comment top

Quinazoline derivatives are the aromatic bicyclic compounds obtained upon the fusion of benzene and pyrimidine rings. Quinazoline analogs are found to be biologically active rendering a variety of therapeutic effects such as anti-inflammatory (Misra et al., 1981), anticancer (Sheng-Li et al., 2005), antihypertensive (Hess et al., 1968), antibacterial (Kung et al., 1999), leishmanicidal (Ram et al., 1990) and antimicrobial (Arfan et al., 2008) activities. The title compound is a quiazoline derivative synthesized as a part of our ongoing project in order to evaluate the biological potential of new derivatives of this important class of organic compounds.

The molecule of the title compound (Fig. 1) is composed of a phenyl (C1–C6) and a nearly planar quinazoline ring (N2–N3/C7–C14; r.m.s. deviation 0.0129 Å) linked through a C6—N1—C7 amino linkage. The bond lengths (Allen et al., 1987) and angles were found to be in normal range. The molecular conformation is stabilized by an intramolecular C5—H5A···N2 hydrogen bond (Table 1). In the crystal, molecules form chains by intermolecular C8—H8A···O3 interactions (symmetry codes as in Table 1, Fig. 2) running parallel to the b axis. The crystal structure is further strengthened by significant π–π stackings: Cg(1)···Cg(2)ⁱ, 3.7148 (10) Å; Cg(1)···Cg(3)ⁱ, 3.7099 (10) Å; Cg(1)··· Cg(3)ⁱⁱ, 3.6438 (10) Å; Cg(1), Cg(2) and Cg(3) are the centroids of the C1–C6, N2/C7/C11/C9/N3/C8 and C9–C14 rings, respectively; symmetry codes: (i) 1-x, 2-y, -z; (ii) -x, 2-y, -z.

Related literature top

For the biological activity of quinazoline derivatives, see: Arfan et al. (2008); Sheng-Li et al. (2005); Kung et al. (1999); Ram et al. (1990); Misra et al. (1981); Hess et al. (1968). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of (E)-N'-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide (0.436 g, 2 mmol) and 2,5-dimethoxyaniline (0.35 g, 2 mmol) was refluxed in acetic acid (12 ml) at 75 °C for 2 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature and neutralized by adding a saturated aqueous solution of sodium bicarbonate until the evolution of CO₂ gas ceased. The reaction mixture yielded brown crystals on standing at room temperature, which were filtered and washed with water. The crystals were re-grown using ethanol and collected in 50.2% yield (0.3273 g). All chemicals were purchased by sigma Aldrich Germany.

Structure description top

For the biological activity of quinazoline derivatives, see: Arfan et al. (2008); Sheng-Li et al. (2005); Kung et al. (1999); Ram et al. (1990); Misra et al. (1981); Hess et al. (1968). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. An intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound. Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.

N-(2,5-Dimethoxyphenyl)-6-nitroquinazolin-4-amine top

Crystal data top

C₁₆H₁₄N₄O₄	Z = 2
M_r = 326.31	F(000) = 340
Triclinic, P1	D_x = 1.451 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2440 (7) Å	Cell parameters from 2914 reflections
b = 10.2832 (10) Å	θ = 2.2–28.2°
c = 11.1622 (11) Å	µ = 0.11 mm⁻¹
α = 72.475 (2)°	T = 298 K
β = 83.663 (2)°	Block, brown
γ = 70.429 (2)°	0.29 × 0.19 × 0.15 mm
V = 747.05 (13) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2792 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scan	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.970, T_max = 0.984	k = −12→12
8510 measured reflections	l = −13→13

Refinement top

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0634P)² + 0.1096P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2792 reflections	Δρ_max = 0.18 e Å⁻³
224 parameters	Δρ_min = −0.20 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: 0.012 (3)

Crystal data top

C₁₆H₁₄N₄O₄	γ = 70.429 (2)°
M_r = 326.31	V = 747.05 (13) Å³
Triclinic, P1	Z = 2
a = 7.2440 (7) Å	Mo Kα radiation
b = 10.2832 (10) Å	µ = 0.11 mm⁻¹
c = 11.1622 (11) Å	T = 298 K
α = 72.475 (2)°	0.29 × 0.19 × 0.15 mm
β = 83.663 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2249 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.984	R_int = 0.021
8510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.18 e Å⁻³
2792 reflections	Δρ_min = −0.20 e Å⁻³
224 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	0.32912 (17)	0.94268 (12)	−0.22927 (10)	0.0562 (3)
O2	0.3236 (2)	1.48679 (13)	−0.24856 (12)	0.0691 (4)
O3	0.1791 (2)	0.42539 (13)	0.34841 (13)	0.0830 (5)
O4	0.2239 (2)	0.50964 (14)	0.15126 (12)	0.0760 (4)
N1	0.25382 (19)	1.01670 (14)	−0.02167 (11)	0.0433 (3)
H1A	0.271 (2)	0.936 (2)	−0.0378 (16)	0.057 (5)*
N2	0.1798 (2)	1.14710 (13)	0.12319 (12)	0.0509 (4)
N3	0.1201 (2)	1.04595 (13)	0.34070 (12)	0.0490 (3)
N4	0.1950 (2)	0.52243 (14)	0.25729 (13)	0.0527 (4)
C1	0.3302 (2)	1.07924 (17)	−0.23984 (14)	0.0458 (4)
C2	0.3659 (2)	1.1756 (2)	−0.34973 (15)	0.0538 (4)
H2B	0.3923	1.1489	−0.4239	0.065*
C3	0.3625 (2)	1.31047 (19)	−0.35023 (15)	0.0553 (4)
H3B	0.3870	1.3742	−0.4244	0.066*
C4	0.3231 (2)	1.35085 (17)	−0.24107 (15)	0.0498 (4)
C5	0.2860 (2)	1.25646 (16)	−0.12990 (15)	0.0470 (4)
H5A	0.2590	1.2843	−0.0563	0.056*
C6	0.2894 (2)	1.12074 (16)	−0.12903 (13)	0.0413 (3)
C7	0.2062 (2)	1.02516 (15)	0.09734 (13)	0.0383 (3)
C8	0.1392 (3)	1.14894 (17)	0.24328 (15)	0.0543 (4)
H8A	0.1223	1.2361	0.2589	0.065*
C9	0.1398 (2)	0.91960 (15)	0.31559 (13)	0.0388 (3)
C10	0.1148 (2)	0.80460 (16)	0.41591 (14)	0.0444 (4)
H10A	0.0859	0.8167	0.4959	0.053*
C11	0.1322 (2)	0.67639 (16)	0.39744 (14)	0.0440 (4)
H11A	0.1156	0.6007	0.4638	0.053*
C12	0.1754 (2)	0.66082 (14)	0.27654 (14)	0.0399 (3)
C13	0.2004 (2)	0.76883 (15)	0.17581 (13)	0.0388 (3)
H13A	0.2281	0.7546	0.0965	0.047*
C14	0.18346 (19)	0.90156 (14)	0.19406 (13)	0.0358 (3)
C15	0.3816 (3)	0.8934 (2)	−0.33839 (17)	0.0663 (5)
H15A	0.3811	0.7959	−0.3187	0.099*
H15B	0.5102	0.8974	−0.3664	0.099*
H15C	0.2889	0.9534	−0.4036	0.099*
C16	0.2820 (3)	1.5289 (2)	−0.1356 (2)	0.0781 (6)
H16A	0.2891	1.6242	−0.1515	0.117*
H16B	0.3760	1.4631	−0.0730	0.117*
H16C	0.1528	1.5278	−0.1061	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0745 (8)	0.0609 (7)	0.0399 (6)	−0.0283 (6)	0.0097 (5)	−0.0198 (5)
O2	0.0911 (9)	0.0502 (7)	0.0614 (8)	−0.0316 (7)	0.0063 (7)	−0.0012 (6)
O3	0.1479 (14)	0.0451 (7)	0.0626 (8)	−0.0462 (8)	0.0084 (8)	−0.0107 (6)
O4	0.1248 (12)	0.0602 (8)	0.0589 (8)	−0.0407 (8)	0.0150 (8)	−0.0326 (6)
N1	0.0579 (8)	0.0396 (7)	0.0338 (7)	−0.0191 (6)	0.0037 (5)	−0.0098 (5)
N2	0.0736 (9)	0.0398 (7)	0.0417 (7)	−0.0227 (6)	0.0058 (6)	−0.0123 (6)
N3	0.0688 (9)	0.0436 (7)	0.0419 (7)	−0.0235 (6)	0.0078 (6)	−0.0189 (6)
N4	0.0701 (9)	0.0434 (7)	0.0505 (8)	−0.0224 (7)	0.0030 (7)	−0.0181 (6)
C1	0.0430 (8)	0.0549 (9)	0.0386 (8)	−0.0169 (7)	0.0003 (6)	−0.0105 (7)
C2	0.0529 (9)	0.0717 (11)	0.0335 (8)	−0.0209 (8)	0.0025 (7)	−0.0098 (7)
C3	0.0542 (10)	0.0614 (10)	0.0399 (9)	−0.0218 (8)	−0.0014 (7)	0.0048 (7)
C4	0.0484 (9)	0.0474 (9)	0.0461 (9)	−0.0165 (7)	−0.0019 (7)	−0.0003 (7)
C5	0.0495 (9)	0.0470 (8)	0.0405 (8)	−0.0164 (7)	0.0007 (7)	−0.0060 (7)
C6	0.0394 (8)	0.0469 (8)	0.0336 (8)	−0.0143 (6)	−0.0016 (6)	−0.0048 (6)
C7	0.0402 (8)	0.0403 (8)	0.0349 (7)	−0.0138 (6)	0.0008 (6)	−0.0109 (6)
C8	0.0794 (12)	0.0412 (8)	0.0498 (9)	−0.0251 (8)	0.0078 (8)	−0.0199 (7)
C9	0.0414 (8)	0.0414 (8)	0.0374 (8)	−0.0154 (6)	0.0023 (6)	−0.0152 (6)
C10	0.0564 (9)	0.0474 (8)	0.0331 (7)	−0.0210 (7)	0.0079 (6)	−0.0146 (6)
C11	0.0518 (9)	0.0432 (8)	0.0375 (8)	−0.0204 (7)	0.0040 (6)	−0.0078 (6)
C12	0.0441 (8)	0.0357 (7)	0.0430 (8)	−0.0140 (6)	0.0001 (6)	−0.0140 (6)
C13	0.0444 (8)	0.0410 (8)	0.0334 (7)	−0.0137 (6)	0.0012 (6)	−0.0142 (6)
C14	0.0359 (7)	0.0377 (7)	0.0341 (7)	−0.0119 (6)	0.0007 (6)	−0.0105 (6)
C15	0.0800 (13)	0.0786 (12)	0.0517 (10)	−0.0321 (10)	0.0150 (9)	−0.0323 (9)
C16	0.1048 (16)	0.0540 (11)	0.0800 (14)	−0.0356 (11)	0.0166 (12)	−0.0196 (10)

Geometric parameters (Å, º) top

O1—C1	1.3761 (19)	C4—C5	1.389 (2)
O1—C15	1.4234 (19)	C5—C6	1.385 (2)
O2—C4	1.376 (2)	C5—H5A	0.9300
O2—C16	1.423 (2)	C7—C14	1.4430 (19)
O3—N4	1.2179 (17)	C8—H8A	0.9300
O4—N4	1.2176 (17)	C9—C10	1.409 (2)
N1—C7	1.3564 (18)	C9—C14	1.4115 (19)
N1—C6	1.4112 (18)	C10—C11	1.358 (2)
N1—H1A	0.868 (19)	C10—H10A	0.9300
N2—C7	1.3182 (19)	C11—C12	1.396 (2)
N2—C8	1.345 (2)	C11—H11A	0.9300
N3—C8	1.302 (2)	C12—C13	1.367 (2)
N3—C9	1.3687 (18)	C13—C14	1.4033 (19)
N4—C12	1.4608 (18)	C13—H13A	0.9300
C1—C2	1.387 (2)	C15—H15A	0.9600
C1—C6	1.397 (2)	C15—H15B	0.9600
C2—C3	1.377 (2)	C15—H15C	0.9600
C2—H2B	0.9300	C16—H16A	0.9600
C3—C4	1.374 (2)	C16—H16B	0.9600
C3—H3B	0.9300	C16—H16C	0.9600

C1—O1—C15	117.06 (13)	N3—C8—H8A	115.4
C4—O2—C16	116.73 (13)	N2—C8—H8A	115.4
C7—N1—C6	129.76 (13)	N3—C9—C10	117.95 (13)
C7—N1—H1A	118.8 (12)	N3—C9—C14	122.40 (13)
C6—N1—H1A	111.4 (12)	C10—C9—C14	119.65 (12)
C7—N2—C8	117.26 (13)	C11—C10—C9	120.95 (13)
C8—N3—C9	114.77 (13)	C11—C10—H10A	119.5
O4—N4—O3	123.00 (13)	C9—C10—H10A	119.5
O4—N4—C12	118.81 (13)	C10—C11—C12	118.47 (13)
O3—N4—C12	118.18 (13)	C10—C11—H11A	120.8
O1—C1—C2	125.36 (14)	C12—C11—H11A	120.8
O1—C1—C6	115.44 (13)	C13—C12—C11	123.04 (13)
C2—C1—C6	119.20 (15)	C13—C12—N4	118.71 (13)
C3—C2—C1	120.74 (15)	C11—C12—N4	118.25 (13)
C3—C2—H2B	119.6	C12—C13—C14	118.91 (13)
C1—C2—H2B	119.6	C12—C13—H13A	120.5
C4—C3—C2	119.96 (14)	C14—C13—H13A	120.5
C4—C3—H3B	120.0	C13—C14—C9	118.98 (12)
C2—C3—H3B	120.0	C13—C14—C7	125.30 (12)
C3—C4—O2	116.71 (14)	C9—C14—C7	115.72 (12)
C3—C4—C5	120.38 (15)	O1—C15—H15A	109.5
O2—C4—C5	122.91 (15)	O1—C15—H15B	109.5
C6—C5—C4	119.81 (15)	H15A—C15—H15B	109.5
C6—C5—H5A	120.1	O1—C15—H15C	109.5
C4—C5—H5A	120.1	H15A—C15—H15C	109.5
C5—C6—C1	119.91 (13)	H15B—C15—H15C	109.5
C5—C6—N1	124.48 (13)	O2—C16—H16A	109.5
C1—C6—N1	115.61 (13)	O2—C16—H16B	109.5
N2—C7—N1	119.40 (13)	H16A—C16—H16B	109.5
N2—C7—C14	120.64 (13)	O2—C16—H16C	109.5
N1—C7—C14	119.95 (12)	H16A—C16—H16C	109.5
N3—C8—N2	129.14 (14)	H16B—C16—H16C	109.5

C15—O1—C1—C2	4.4 (2)	C7—N2—C8—N3	−0.5 (3)
C15—O1—C1—C6	−176.33 (14)	C8—N3—C9—C10	−178.01 (14)
O1—C1—C2—C3	179.65 (14)	C8—N3—C9—C14	1.9 (2)
C6—C1—C2—C3	0.4 (2)	N3—C9—C10—C11	179.96 (14)
C1—C2—C3—C4	−0.2 (2)	C14—C9—C10—C11	0.0 (2)
C2—C3—C4—O2	179.56 (14)	C9—C10—C11—C12	0.0 (2)
C2—C3—C4—C5	−0.1 (2)	C10—C11—C12—C13	−0.2 (2)
C16—O2—C4—C3	179.79 (16)	C10—C11—C12—N4	179.70 (13)
C16—O2—C4—C5	−0.6 (2)	O4—N4—C12—C13	−3.3 (2)
C3—C4—C5—C6	0.2 (2)	O3—N4—C12—C13	177.54 (14)
O2—C4—C5—C6	−179.49 (14)	O4—N4—C12—C11	176.73 (14)
C4—C5—C6—C1	0.1 (2)	O3—N4—C12—C11	−2.4 (2)
C4—C5—C6—N1	−179.94 (13)	C11—C12—C13—C14	0.5 (2)
O1—C1—C6—C5	−179.67 (13)	N4—C12—C13—C14	−179.45 (12)
C2—C1—C6—C5	−0.4 (2)	C12—C13—C14—C9	−0.5 (2)
O1—C1—C6—N1	0.34 (19)	C12—C13—C14—C7	179.88 (13)
C2—C1—C6—N1	179.66 (13)	N3—C9—C14—C13	−179.70 (13)
C7—N1—C6—C5	1.8 (2)	C10—C9—C14—C13	0.2 (2)
C7—N1—C6—C1	−178.23 (14)	N3—C9—C14—C7	0.0 (2)
C8—N2—C7—N1	−177.84 (14)	C10—C9—C14—C7	179.89 (12)
C8—N2—C7—C14	2.6 (2)	N2—C7—C14—C13	177.34 (13)
C6—N1—C7—N2	2.7 (2)	N1—C7—C14—C13	−2.2 (2)
C6—N1—C7—C14	−177.71 (13)	N2—C7—C14—C9	−2.3 (2)
C9—N3—C8—N2	−1.8 (3)	N1—C7—C14—C9	178.10 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2	0.93	2.22	2.833 (2)	123
C8—H8A···O3ⁱ	0.93	2.60	3.490 (2)	161

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄O₄
M_r	326.31
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.2440 (7), 10.2832 (10), 11.1622 (11)
α, β, γ (°)	72.475 (2), 83.663 (2), 70.429 (2)
V (Å³)	747.05 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.29 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.970, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8510, 2792, 2249
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.05
No. of reflections	2792
No. of parameters	224
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2	0.9300	2.2200	2.833 (2)	123.00
C8—H8A···O3ⁱ	0.9300	2.6000	3.490 (2)	161.00

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan (project No. 20–2073) and the Pakistan Academy of Sciences (PAS) for their financial support.

References

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