3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinyl­idene]chroman-2,4-dione

Jashari, A.; Popovski, E.; Mikhova, B.; Nikolova, R.P.; Shivachev, B.L.

doi:10.1107/S1600536813000858

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o258

doi:10.1107/S1600536813000858

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3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinylidene]chroman-2,4-dione

Ahmed Jashari,^a Emil Popovski,^b ^* Bozhana Mikhova,^c Rositsa P. Nikolova ^d and Boris L. Shivachev ^d

^aGroup of Physics & Chemistry, Faculty of Natural Sciences & Mathematics, State University of Tetovo, 1200 Tetovo, Macedonia, ^bInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Arhimedova 5, 1000 Skopje, Macedonia, ^cInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. build. 9, 1113 Sofia, Bulgaria, and ^dInstitute of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia, Bulgaria
^*Correspondence e-mail: popovski.emil@gmail.com

(Received 21 December 2012; accepted 9 January 2013; online 19 January 2013)

In the title compound, C₁₆H₁₅N₃O₄, the dihedral angle between the chromane and isoxazole rings [r.m.s. deviations = 0.042 and 0.007 Å, respectively] is 20.33 (12)°. The molecular geometry is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, N—H⋯O hydrogen bonds generate chains along the c-axis direction. The crystal studied was a non-morohedral twin.

Related literature

For general background to the use of coumarin derivatives in organic synthesis and as biologically active compounds see: Adavi et al. (2004 ); Shi & Zhou (2011 ); Toshihiro et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₅N₃O₄
M_r = 313.31
Monoclinic, P 2₁ /c
a = 13.431 (14) Å
b = 9.1803 (9) Å
c = 12.638 (4) Å
β = 100.49 (8)°
V = 1532.3 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 290 K
0.28 × 0.26 × 0.21 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.584, T_max = 1.000
13050 measured reflections
3010 independent reflections
2148 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.181
S = 1.09
3010 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.89 (4)	1.86 (4)	2.581 (3)	137 (4)
N2—H2⋯O9ⁱ	0.89 (4)	2.70 (4)	3.249 (4)	121 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000858/kp2443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000858/kp2443Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000858/kp2443Isup3.cml

checkCIF report

Comment top

Synthesis of novel coumarin derivatives is rapid ongoing process in the world due to the remarkable broad spectrum of pharmacological activities, especially anticancer (Toshihiro, et al., 2005; Shi & Zhou, 2011; Adavi, et al., 2004). Our interest is to develop novel coumarin compounds as efficient antitumor agents. Herein, we report the crystal structure of the title compound.

The title compound (Fig. 1) possesses two distinct functional groups: 3-iminochroman-2,4-dione, and 5-(tert-butyl)isoxazole. The chromane and isoxazole moieties are nearly planar (with respective r.m.s. of 0.042 and 0.007 Å).

The interplanar angle between the chromane and isoxazole is 20.33 (12)°. The molecular geometry is stabilised by the intramolecular hydrogen bond N2—H2···O2 (Table 1). In the crystal structure the molecules are connected by the N—H···O hydrogen bond forming chains along c (Fig. 2).

Related literature top

For general background to the use of coumarin derivatives in organic synthesis and as biologically active compounds see: Adavi et al. (2004); Shi & Zhou (2011); Toshihiro et al. (2005).

Experimental top

Suitable crystals of the title compound were obtained by slow evaporation from ethanol at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. View of the structure and the atom-numbering scheme of the title compound showing 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of the molecules in the unit cell, showing the hydrogen-bonding interactions as dotted lines. [symmetry code: (i) x, 1/2 - y, 1/2 + z].

3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinylidene]chroman-2,4-dione top

Crystal data top

C₁₆H₁₅N₃O₄	F(000) = 656
M_r = 313.31	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 419 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.7107 Å
a = 13.431 (14) Å	Cell parameters from 4079 reflections
b = 9.1803 (9) Å	θ = 3.0–29.4°
c = 12.638 (4) Å	µ = 0.10 mm⁻¹
β = 100.49 (8)°	T = 290 K
V = 1532.3 (17) Å³	Prism, yellow
Z = 4	0.28 × 0.26 × 0.21 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3010 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2148 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.085
Detector resolution: 10.3974 pixels mm^-1	θ_max = 29.4°, θ_min = 3.0°
ω scans	h = −16→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→12
T_min = 0.584, T_max = 1.000	l = −15→16
13050 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0555P)² + 1.4334P] where P = (F_o² + 2F_c²)/3
3010 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₄	V = 1532.3 (17) Å³
M_r = 313.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.431 (14) Å	µ = 0.10 mm⁻¹
b = 9.1803 (9) Å	T = 290 K
c = 12.638 (4) Å	0.28 × 0.26 × 0.21 mm
β = 100.49 (8)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3010 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2148 reflections with I > 2σ(I)
T_min = 0.584, T_max = 1.000	R_int = 0.085
13050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.23 e Å⁻³
3010 reflections	Δρ_min = −0.16 e Å⁻³
215 parameters

Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)

FTIR (KBr): 1377 cm^-1 (CH₃ δ_s), 1467.5 cm^-1 (N=N), 1740 cm^-1 (C=O).

NMR atom numbering is according to IUPAC

¹³C NMR (62.9 MHz, DMSO-d6): δ 28.2 (CH₃), 32.1 (C t-but), 91.2 (NCCH), 117.4 (C8 of the coumarin ring), 120.4 (C4a of the coumarin ring), 124.9 (C6 of the coumarin ring), 125.7 (C3 of the coumarin ring), 126.8 (C5 of the coumarin ring), 137.0 (C7 of the coumarin ring), 154.1(C8a of the coumarin ring), 157.6 (C2 of the coumarin ring), 162.4 (NCCH), 178.3 (C4 of the coumarin ring), 182.8 (NC).

¹H NMR (250 MHz, DMSO-d₆): δ 1.35 (s, 9H, t-but.), 6.57 (s,1H of the isoxazol ring), 7.37 (dd, J = 8.0, 1.5 Hz, 1H, H8 of the coumarin ring), 7.39 (ddd, J = 8.0, 8.0, 1.5 Hz, 1H, H6 of the coumarin ring), 7.80 (ddd, J = 8.0, 8.0, 1.5 Hz, 1H, C7 of the coumarin ring), 8.00 (dd,1H, dd, J = 8.0, 1.5 Hz, C5 of the coumarin ring).

Elemental analysis: C, 61.34; H, 4.83; N, 13.41. TOF MS ES+: m/e: 336[M+Na]⁺.

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
C1	0.1628 (2)	0.3116 (3)	0.0511 (2)	0.0362 (6)
C2	0.1605 (2)	0.4578 (3)	0.0958 (2)	0.0384 (6)
C3	0.1281 (2)	0.5746 (3)	0.0182 (2)	0.0369 (6)
C4	0.1307 (2)	0.7207 (3)	0.0498 (3)	0.0467 (7)
H4	0.1511	0.7448	0.1219	0.056*
C5	0.1035 (3)	0.8282 (3)	−0.0247 (3)	0.0571 (9)
H5	0.1074	0.9254	−0.0035	0.068*
C6	0.0701 (3)	0.7922 (4)	−0.1321 (3)	0.0580 (9)
H6	0.0509	0.8657	−0.1823	0.070*
C7	0.0651 (3)	0.6488 (4)	−0.1651 (3)	0.0508 (8)
H7	0.0421	0.6250	−0.2369	0.061*
C8	0.0948 (2)	0.5405 (3)	−0.0893 (2)	0.0389 (6)
C9	0.1240 (2)	0.2823 (3)	−0.0636 (2)	0.0402 (6)
C10	0.2869 (2)	0.0916 (3)	0.2637 (2)	0.0408 (6)
C11	0.3172 (2)	−0.0401 (3)	0.2229 (2)	0.0421 (7)
H11	0.3060	−0.0719	0.1519	0.051*
C12	0.3667 (2)	−0.1101 (3)	0.3116 (2)	0.0432 (7)
C13	0.4211 (3)	−0.2535 (3)	0.3317 (3)	0.0494 (8)
C14	0.5276 (3)	−0.2268 (4)	0.3960 (3)	0.0741 (12)
H14A	0.5637	−0.1627	0.3563	0.111*
H14B	0.5630	−0.3178	0.4080	0.111*
H14C	0.5229	−0.1831	0.4639	0.111*
C15	0.3615 (4)	−0.3513 (5)	0.3961 (4)	0.0790 (12)
H15A	0.3550	−0.3036	0.4621	0.118*
H15B	0.3967	−0.4419	0.4119	0.118*
H15C	0.2954	−0.3696	0.3546	0.118*
C16	0.4268 (4)	−0.3246 (5)	0.2235 (3)	0.0769 (12)
H16A	0.3597	−0.3363	0.1827	0.115*
H16B	0.4586	−0.4183	0.2356	0.115*
H16C	0.4657	−0.2640	0.1844	0.115*
N1	0.20237 (19)	0.1960 (3)	0.10479 (18)	0.0390 (5)
N2	0.2352 (2)	0.2092 (3)	0.20786 (19)	0.0429 (6)
N3	0.3136 (2)	0.1048 (3)	0.3673 (2)	0.0549 (7)
O1	0.08744 (16)	0.3990 (2)	−0.12688 (14)	0.0433 (5)
O2	0.18801 (19)	0.4820 (2)	0.19257 (15)	0.0562 (6)
O3	0.36552 (18)	−0.0258 (3)	0.39890 (16)	0.0558 (6)
O9	0.1194 (2)	0.1661 (2)	−0.10662 (17)	0.0594 (7)
H2	0.231 (3)	0.296 (5)	0.238 (3)	0.076 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0388 (15)	0.0349 (14)	0.0353 (14)	−0.0036 (11)	0.0082 (11)	0.0027 (10)
C2	0.0438 (16)	0.0395 (15)	0.0313 (13)	−0.0033 (12)	0.0057 (11)	0.0029 (11)
C3	0.0358 (14)	0.0379 (14)	0.0372 (13)	−0.0038 (11)	0.0071 (11)	0.0043 (11)
C4	0.0489 (18)	0.0393 (16)	0.0515 (17)	−0.0027 (13)	0.0079 (14)	−0.0030 (13)
C5	0.064 (2)	0.0336 (16)	0.076 (2)	−0.0014 (14)	0.0165 (19)	0.0061 (14)
C6	0.055 (2)	0.0499 (19)	0.067 (2)	0.0043 (15)	0.0054 (17)	0.0252 (16)
C7	0.0509 (19)	0.0549 (19)	0.0435 (16)	0.0002 (15)	0.0000 (14)	0.0131 (14)
C8	0.0362 (14)	0.0378 (14)	0.0420 (14)	−0.0032 (11)	0.0047 (12)	0.0046 (11)
C9	0.0434 (16)	0.0399 (15)	0.0374 (14)	−0.0035 (12)	0.0072 (12)	0.0014 (12)
C10	0.0366 (14)	0.0439 (16)	0.0408 (14)	0.0000 (12)	0.0043 (11)	0.0022 (12)
C11	0.0395 (15)	0.0507 (17)	0.0341 (13)	−0.0037 (13)	0.0011 (11)	0.0016 (12)
C12	0.0389 (16)	0.0498 (18)	0.0394 (15)	0.0017 (12)	0.0034 (12)	−0.0018 (12)
C13	0.0468 (18)	0.0475 (18)	0.0500 (17)	0.0080 (14)	−0.0015 (14)	−0.0013 (13)
C14	0.048 (2)	0.070 (2)	0.091 (3)	0.0149 (18)	−0.0216 (19)	−0.004 (2)
C15	0.088 (3)	0.060 (2)	0.087 (3)	0.002 (2)	0.011 (2)	0.016 (2)
C16	0.082 (3)	0.072 (3)	0.073 (3)	0.025 (2)	0.006 (2)	−0.018 (2)
N1	0.0403 (13)	0.0437 (13)	0.0329 (11)	−0.0042 (10)	0.0064 (10)	0.0017 (9)
N2	0.0500 (15)	0.0410 (14)	0.0355 (12)	0.0030 (11)	0.0022 (11)	0.0009 (10)
N3	0.0614 (18)	0.0571 (17)	0.0414 (14)	0.0205 (13)	−0.0029 (12)	−0.0005 (12)
O1	0.0517 (12)	0.0418 (11)	0.0336 (10)	−0.0026 (9)	0.0000 (9)	0.0015 (8)
O2	0.0862 (18)	0.0425 (12)	0.0360 (11)	−0.0027 (11)	0.0010 (11)	−0.0033 (9)
O3	0.0627 (15)	0.0603 (14)	0.0393 (11)	0.0232 (11)	−0.0041 (10)	0.0009 (10)
O9	0.0917 (19)	0.0402 (12)	0.0429 (12)	−0.0031 (11)	0.0028 (12)	−0.0056 (9)

Geometric parameters (Å, º) top

C1—N1	1.319 (4)	C10—N2	1.403 (4)
C1—C2	1.459 (4)	C11—C12	1.356 (4)
C1—C9	1.473 (4)	C11—H11	0.9300
C2—O2	1.231 (3)	C12—O3	1.350 (4)
C2—C3	1.465 (4)	C12—C13	1.505 (4)
C3—C8	1.386 (4)	C13—C16	1.530 (5)
C3—C4	1.397 (4)	C13—C14	1.531 (5)
C4—C5	1.367 (5)	C13—C15	1.531 (6)
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.390 (5)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—C7	1.379 (5)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.388 (4)	C15—H15C	0.9600
C7—H7	0.9300	C16—H16A	0.9600
C8—O1	1.381 (3)	C16—H16B	0.9600
C9—O9	1.194 (3)	C16—H16C	0.9600
C9—O1	1.373 (3)	N1—N2	1.303 (3)
C10—N3	1.299 (4)	N2—H2	0.89 (4)
C10—C11	1.404 (4)	N3—O3	1.408 (3)

N1—C1—C2	125.2 (2)	O3—C12—C13	116.1 (2)
N1—C1—C9	113.4 (2)	C11—C12—C13	134.8 (3)
C2—C1—C9	121.4 (2)	C12—C13—C16	108.9 (3)
O2—C2—C1	121.8 (2)	C12—C13—C14	109.1 (3)
O2—C2—C3	122.1 (3)	C16—C13—C14	110.4 (3)
C1—C2—C3	116.0 (2)	C12—C13—C15	108.6 (3)
C8—C3—C4	118.9 (3)	C16—C13—C15	109.9 (3)
C8—C3—C2	119.6 (2)	C14—C13—C15	109.9 (3)
C4—C3—C2	121.5 (3)	C13—C14—H14A	109.5
C5—C4—C3	120.5 (3)	C13—C14—H14B	109.5
C5—C4—H4	119.8	H14A—C14—H14B	109.5
C3—C4—H4	119.8	C13—C14—H14C	109.5
C4—C5—C6	119.9 (3)	H14A—C14—H14C	109.5
C4—C5—H5	120.0	H14B—C14—H14C	109.5
C6—C5—H5	120.0	C13—C15—H15A	109.5
C7—C6—C5	120.8 (3)	C13—C15—H15B	109.5
C7—C6—H6	119.6	H15A—C15—H15B	109.5
C5—C6—H6	119.6	C13—C15—H15C	109.5
C6—C7—C8	118.9 (3)	H15A—C15—H15C	109.5
C6—C7—H7	120.5	H15B—C15—H15C	109.5
C8—C7—H7	120.5	C13—C16—H16A	109.5
O1—C8—C3	122.7 (2)	C13—C16—H16B	109.5
O1—C8—C7	116.3 (3)	H16A—C16—H16B	109.5
C3—C8—C7	121.0 (3)	C13—C16—H16C	109.5
O9—C9—O1	116.7 (3)	H16A—C16—H16C	109.5
O9—C9—C1	126.2 (3)	H16B—C16—H16C	109.5
O1—C9—C1	117.1 (2)	N2—N1—C1	118.1 (2)
N3—C10—C11	113.9 (3)	N1—N2—C10	118.5 (3)
N3—C10—N2	117.1 (3)	N1—N2—H2	118 (3)
C11—C10—N2	129.0 (3)	C10—N2—H2	123 (3)
C12—C11—C10	103.6 (2)	C10—N3—O3	103.7 (2)
C12—C11—H11	128.2	C9—O1—C8	122.6 (2)
C10—C11—H11	128.2	C12—O3—N3	109.6 (2)
O3—C12—C11	109.1 (3)

N1—C1—C2—O2	−7.1 (5)	N2—C10—C11—C12	177.9 (3)
C9—C1—C2—O2	176.2 (3)	C10—C11—C12—O3	0.2 (3)
N1—C1—C2—C3	170.3 (3)	C10—C11—C12—C13	−178.8 (4)
C9—C1—C2—C3	−6.4 (4)	O3—C12—C13—C16	−172.7 (3)
O2—C2—C3—C8	−177.9 (3)	C11—C12—C13—C16	6.2 (5)
C1—C2—C3—C8	4.8 (4)	O3—C12—C13—C14	−52.1 (4)
O2—C2—C3—C4	2.7 (4)	C11—C12—C13—C14	126.8 (4)
C1—C2—C3—C4	−174.7 (3)	O3—C12—C13—C15	67.7 (4)
C8—C3—C4—C5	−1.8 (5)	C11—C12—C13—C15	−113.4 (4)
C2—C3—C4—C5	177.7 (3)	C2—C1—N1—N2	5.7 (4)
C3—C4—C5—C6	1.9 (5)	C9—C1—N1—N2	−177.3 (3)
C4—C5—C6—C7	−0.7 (6)	C1—N1—N2—C10	−173.5 (3)
C5—C6—C7—C8	−0.6 (5)	N3—C10—N2—N1	−176.1 (3)
C4—C3—C8—O1	−178.3 (3)	C11—C10—N2—N1	5.8 (5)
C2—C3—C8—O1	2.2 (4)	C11—C10—N3—O3	0.2 (4)
C4—C3—C8—C7	0.5 (4)	N2—C10—N3—O3	−178.2 (2)
C2—C3—C8—C7	−179.0 (3)	O9—C9—O1—C8	−175.2 (3)
C6—C7—C8—O1	179.6 (3)	C1—C9—O1—C8	6.2 (4)
C6—C7—C8—C3	0.7 (5)	C3—C8—O1—C9	−8.2 (4)
N1—C1—C9—O9	5.7 (5)	C7—C8—O1—C9	173.0 (3)
C2—C1—C9—O9	−177.3 (3)	C11—C12—O3—N3	−0.1 (4)
N1—C1—C9—O1	−175.9 (2)	C13—C12—O3—N3	179.1 (3)
C2—C1—C9—O1	1.2 (4)	C10—N3—O3—C12	−0.1 (4)
N3—C10—C11—C12	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.89 (4)	1.86 (4)	2.581 (3)	137 (4)
N2—H2···O9ⁱ	0.89 (4)	2.70 (4)	3.249 (4)	121 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₄
M_r	313.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	13.431 (14), 9.1803 (9), 12.638 (4)
β (°)	100.49 (8)
V (Å³)	1532.3 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.26 × 0.21

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.584, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13050, 3010, 2148
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.181, 1.09
No. of reflections	3010
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.89 (4)	1.86 (4)	2.581 (3)	137 (4)
N2—H2···O9ⁱ	0.89 (4)	2.70 (4)	3.249 (4)	121 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

Thanks are due to Bulgarian National Science Fund of the Ministry of Education, Youth and Science for financial support (grants/contracts DRNF02/1 and DRNF02/13).

References

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