6-Ethyl-N-methyl-3-nitro-4-nitro­methyl-4H-chromen-2-amine

Muthukumaran, J.; Parthiban, A.; Surya Prakash Rao, H.; Krishna, R.

doi:10.1107/S1600536811053554

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o180-o181

doi:10.1107/S1600536811053554

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6-Ethyl-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine

J. Muthukumaran,^a A. Parthiban,^b H. Surya Prakash Rao ^b ‡ and R. Krishna ^a ^*

^aCentre for Bioinformatics, Pondicherry University, Puducherry 605 014, India, and ^bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
^*Correspondence e-mail: krishstrucbio@gmail.com

(Received 23 November 2011; accepted 12 December 2011; online 21 December 2011)

In the title compound, C₁₃H₁₅N₃O₅, the O and N atoms of the nitromethyl group and the methyl C atom of the ethyl group are disordered over two sets of sites with refined occupancies of 0.629 (7):0.371 (7) and 0.533 (8):0.467 (8), respectively. The dihydropyran ring has an extremely flattened conformation. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, pairs of N—H⋯O hydrogen bonds link molecules, forming inversion dimers. In addition, weak intermolecular C—H⋯O hydrogen bonds are also present.

Related literature

For the biological and pharmacological importance of 4H-chromene derivatives, see: Cai (2007 , 2008 ); Cai et al. (2006 ); Gabor (1988 ); Brooks (1998 ); Hyana & Saimoto (1987 ); Tang et al. (2007 ). For related structures, see: Muthukumaran et al. (2011a ,b ,c ); Gayathri et al. (2006 ); Bhaskaran et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₅N₃O₅
M_r = 293.28
Triclinic, $[P \overline 1]$
a = 8.2538 (10) Å
b = 9.0431 (9) Å
c = 10.3323 (12) Å
α = 73.484 (9)°
β = 71.728 (11)°
γ = 83.234 (9)°
V = 701.75 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.4 × 0.35 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.958, T_max = 0.979
4281 measured reflections
2463 independent reflections
1520 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.232
S = 1.06
2463 reflections
205 parameters
122 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.97	2.600 (3)	129
N1—H1⋯O2ⁱ	0.86	2.21	2.943 (4)	143
C11—H11A⋯O3ⁱⁱ	0.97	2.58	3.258 (4)	128
C12—H12A⋯O2ⁱⁱⁱ	0.97	2.55	3.457 (5)	156
Symmetry codes: (i) -x+1, -y+1, -z+3; (ii) -x+2, -y+1, -z+2; (iii) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053554/lh5388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053554/lh5388Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053554/lh5388Isup3.cml

checkCIF report

Comment top

The 4H-chromene moiety frequently appears as a main structural component in various biologically important compounds. They exhibit the various pharmacological properties such as anti-coagulant, anti-viral, anti-fungal, anti-inflammatory, anti-diabetic and anti-cancer activity (Cai, 2008; Cai, 2007; Cai et al., 2006; Gabor et al., 1988; Brooks, 1998; Hyana & Saimoto, 1987; Tang et al., 2007). Considering the growing medicinal importance of these derivatives, an X-ray crystallographic study on the title compound was carried out. In the molecular structure of the title compound (I) (Fig. 1) the O and N atoms of the nitromethyl group and the methyl C atom of the ethyl group are disordered over two sets of sites with refined occupancies of 0.629 (7):0.371 (7) and 0.533 (8):0.467 (8), respectively. Some crystal structures of related 4H-chromene derivatives have already been published e.g. N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine (Muthukumaran et al., 2011c), 6,8-dichloro-N-methyl-3-nitro-4-nitro-methyl-4H-chromen-2-amine (Muthukumaran et al., 2011a), 6-methoxy-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine (Muthukumaran et al., 2011b), N-benzyl-N-[4-methylsulfanyl)-3-nitro-4H-chromen-2-yl] amine (Bhaskaran et al., 2006) and N,6-dimethyl-4-(methylsulfanyl)-3-nitro-4H-chromen-2-amine (Gayathri et al., 2006). In the crystal, N—H···O hydrogen bonds form centrosymmetric dimers (Fig .2). In addition, there are weak intermolecular C—H···O hydrogen bonds.

Related literature top

For the biological and pharmacological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Gabor et al. (1988); Brooks (1998); Hyana & Saimoto (1987); Tang et al. (2007). For related structures, see: Muthukumaran et al. (2011a,b,c); Gayathri et al. (2006); Bhaskaran et al. (2006).

Experimental top

To a solution of (E)-5-ethyl-2-(2-nitrovinyl)phenol (150 mg, 0.77 mmol) in methanol (5 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (15 mg, 0.10 mmol) was added and stirred for 10 minutes at room temperature. To this solution (E) N-methyl-1-(methylthio)-2-nitroethenamine (115 mg, 0.77 mmol) was added and stirred for 8 h until completion of the reaction (TLC, hexane:ethyl acetate, 3:2, Rf = 1/2). The reaction mixture was then kept aside at 278 K in a refrigerator for 3 h to afford racemic mixture of the product as a white precipitate, which was filtered. Good crystals were obtained by recrystallization of a solution of dichloromethane: hexane (9:3 v/v).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

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

6-Ethyl-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine top

Crystal data top

C₁₃H₁₅N₃O₅	Z = 2
M_r = 293.28	F(000) = 308
Triclinic, P1	D_x = 1.388 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2538 (10) Å	Cell parameters from 1935 reflections
b = 9.0431 (9) Å	θ = 2.7–29.1°
c = 10.3323 (12) Å	µ = 0.11 mm⁻¹
α = 73.484 (9)°	T = 293 K
β = 71.728 (11)°	Block, colorless
γ = 83.234 (9)°	0.4 × 0.35 × 0.2 mm
V = 701.75 (14) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2463 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 15.9821 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
T_min = 0.958, T_max = 0.979	l = −11→12
4281 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.232	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1377P)² + 0.1022P] where P = (F_o² + 2F_c²)/3
2463 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.40 e Å⁻³
122 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₃H₁₅N₃O₅	γ = 83.234 (9)°
M_r = 293.28	V = 701.75 (14) Å³
Triclinic, P1	Z = 2
a = 8.2538 (10) Å	Mo Kα radiation
b = 9.0431 (9) Å	µ = 0.11 mm⁻¹
c = 10.3323 (12) Å	T = 293 K
α = 73.484 (9)°	0.4 × 0.35 × 0.2 mm
β = 71.728 (11)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2463 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1520 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.979	R_int = 0.031
4281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	122 restraints
wR(F²) = 0.232	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
2463 reflections	Δρ_min = −0.34 e Å⁻³
205 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	Occ. (<1)
O1	0.4139 (2)	0.2857 (3)	1.1942 (2)	0.0468 (6)
C1	0.5007 (4)	0.2700 (4)	1.0581 (3)	0.0401 (8)
C8	0.6569 (4)	0.4021 (4)	1.1982 (3)	0.0383 (8)
O2	0.6415 (3)	0.5176 (3)	1.3724 (2)	0.0569 (7)
O3	0.8792 (3)	0.5209 (3)	1.2039 (2)	0.0636 (8)
N2	0.7266 (3)	0.4819 (3)	1.2608 (3)	0.0435 (7)
C9	0.4856 (4)	0.3561 (4)	1.2598 (3)	0.0394 (8)
N1	0.3831 (3)	0.3738 (3)	1.3790 (3)	0.0490 (8)
H1	0.4224	0.4167	1.4267	0.059*
C6	0.6684 (4)	0.3088 (4)	0.9922 (3)	0.0380 (8)
C2	0.4066 (4)	0.2138 (4)	0.9941 (4)	0.0490 (9)
H2	0.2935	0.1877	1.0408	0.059*
C5	0.7416 (4)	0.2899 (4)	0.8563 (3)	0.0489 (9)
H5	0.8551	0.3151	0.8099	0.059*
C7	0.7700 (4)	0.3607 (4)	1.0681 (3)	0.0413 (8)
H7	0.8238	0.4563	1.0044	0.050*
C4	0.6519 (5)	0.2354 (4)	0.7888 (4)	0.0528 (9)
C3	0.4833 (5)	0.1970 (4)	0.8600 (4)	0.0548 (10)
H3	0.4209	0.1592	0.8160	0.066*
C11	0.9145 (4)	0.2466 (4)	1.0924 (4)	0.0588 (10)
H11A	0.9964	0.2440	1.0021	0.071*
H11B	0.9726	0.2804	1.1468	0.071*
N3A	0.8506 (10)	0.0891 (5)	1.1687 (9)	0.085 (2)	0.629 (7)
O4A	0.7196 (14)	0.0755 (17)	1.2654 (17)	0.113 (3)	0.629 (7)
O5A	0.9064 (12)	−0.0297 (9)	1.1366 (11)	0.169 (3)	0.629 (7)
N3B	0.8580 (16)	0.0962 (10)	1.1944 (16)	0.085 (2)	0.371 (7)
O4B	0.717 (2)	0.043 (3)	1.240 (3)	0.113 (3)	0.371 (7)
O5B	0.9759 (19)	0.0179 (16)	1.2268 (18)	0.169 (3)	0.371 (7)
C12	0.7376 (6)	0.2240 (6)	0.6386 (4)	0.0778 (13)
H12A	0.7279	0.3246	0.5751	0.093*	0.533 (8)
H12B	0.8581	0.2008	0.6277	0.093*	0.533 (8)
H12C	0.6550	0.2506	0.5857	0.093*	0.467 (8)
H12D	0.8286	0.2970	0.5932	0.093*	0.467 (8)
C13A	0.6702 (15)	0.1062 (12)	0.5913 (10)	0.114 (3)	0.533 (8)
H13A	0.7334	0.1097	0.4951	0.171*	0.533 (8)
H13B	0.5517	0.1291	0.5983	0.171*	0.533 (8)
H13C	0.6828	0.0050	0.6506	0.171*	0.533 (8)
C13B	0.8100 (18)	0.0627 (8)	0.6369 (12)	0.114 (3)	0.467 (8)
H13D	0.8636	0.0583	0.5411	0.171*	0.467 (8)
H13E	0.7197	−0.0094	0.6804	0.171*	0.467 (8)
H13F	0.8929	0.0369	0.6881	0.171*	0.467 (8)
C10	0.2057 (4)	0.3261 (6)	1.4383 (4)	0.0722 (13)
H10A	0.1380	0.3912	1.3825	0.108*
H10B	0.1624	0.3350	1.5336	0.108*
H10C	0.2001	0.2209	1.4376	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0348 (11)	0.0592 (17)	0.0485 (13)	−0.0089 (10)	−0.0032 (9)	−0.0247 (11)
C1	0.0371 (16)	0.041 (2)	0.0445 (17)	0.0043 (14)	−0.0130 (14)	−0.0158 (14)
C8	0.0367 (16)	0.039 (2)	0.0394 (16)	−0.0034 (13)	−0.0094 (13)	−0.0109 (14)
O2	0.0646 (15)	0.0694 (19)	0.0409 (12)	−0.0110 (13)	−0.0074 (11)	−0.0262 (12)
O3	0.0457 (14)	0.085 (2)	0.0667 (16)	−0.0271 (13)	−0.0008 (12)	−0.0383 (15)
N2	0.0472 (16)	0.0450 (18)	0.0393 (14)	−0.0071 (12)	−0.0081 (12)	−0.0155 (13)
C9	0.0362 (16)	0.0365 (19)	0.0431 (17)	0.0004 (13)	−0.0080 (14)	−0.0114 (14)
N1	0.0431 (15)	0.058 (2)	0.0448 (15)	−0.0076 (13)	0.0022 (12)	−0.0255 (14)
C6	0.0404 (17)	0.0360 (19)	0.0386 (16)	0.0007 (13)	−0.0114 (13)	−0.0126 (14)
C2	0.0420 (18)	0.050 (2)	0.063 (2)	0.0021 (15)	−0.0210 (16)	−0.0223 (18)
C5	0.0472 (18)	0.051 (2)	0.0468 (19)	−0.0022 (16)	−0.0073 (15)	−0.0175 (16)
C7	0.0361 (16)	0.047 (2)	0.0416 (17)	−0.0084 (14)	−0.0050 (13)	−0.0173 (15)
C4	0.064 (2)	0.052 (2)	0.0476 (19)	0.0046 (17)	−0.0212 (17)	−0.0185 (17)
C3	0.066 (2)	0.050 (2)	0.063 (2)	0.0010 (18)	−0.0350 (19)	−0.0208 (18)
C11	0.0356 (17)	0.080 (3)	0.074 (2)	0.0052 (17)	−0.0169 (16)	−0.042 (2)
N3A	0.075 (3)	0.079 (3)	0.095 (4)	0.044 (2)	−0.033 (2)	−0.023 (2)
O4A	0.131 (3)	0.045 (7)	0.154 (7)	−0.008 (3)	−0.030 (3)	−0.021 (4)
O5A	0.189 (6)	0.098 (5)	0.222 (9)	0.055 (5)	−0.065 (5)	−0.065 (5)
N3B	0.075 (3)	0.079 (3)	0.095 (4)	0.044 (2)	−0.033 (2)	−0.023 (2)
O4B	0.131 (3)	0.045 (7)	0.154 (7)	−0.008 (3)	−0.030 (3)	−0.021 (4)
O5B	0.189 (6)	0.098 (5)	0.222 (9)	0.055 (5)	−0.065 (5)	−0.065 (5)
C12	0.100 (3)	0.084 (3)	0.056 (2)	−0.003 (3)	−0.022 (2)	−0.031 (2)
C13A	0.168 (10)	0.096 (6)	0.073 (5)	−0.015 (6)	0.000 (5)	−0.049 (4)
C13B	0.168 (10)	0.096 (6)	0.073 (5)	−0.015 (6)	0.000 (5)	−0.049 (4)
C10	0.046 (2)	0.092 (4)	0.073 (3)	−0.015 (2)	0.0122 (19)	−0.041 (2)

Geometric parameters (Å, º) top

O1—C9	1.342 (4)	C11—N3B	1.4847 (11)
O1—C1	1.403 (3)	C11—N3A	1.4847 (11)
C1—C6	1.375 (4)	C11—H11A	0.9700
C1—C2	1.380 (4)	C11—H11B	0.9700
C8—N2	1.366 (4)	N3A—O4A	1.2113 (11)
C8—C9	1.414 (4)	N3A—O5A	1.2115 (11)
C8—C7	1.496 (4)	N3B—O4B	1.2114 (11)
O2—N2	1.256 (3)	N3B—O5B	1.2117 (11)
O3—N2	1.256 (3)	C12—C13B	1.5122 (11)
C9—N1	1.298 (4)	C12—C13A	1.5125 (11)
N1—C10	1.463 (4)	C12—H12A	0.9700
N1—H1	0.8600	C12—H12B	0.9700
C6—C5	1.395 (4)	C12—H12C	0.9700
C6—C7	1.501 (4)	C12—H12D	0.9700
C2—C3	1.376 (5)	C13A—H13A	0.9600
C2—H2	0.9300	C13A—H13B	0.9600
C5—C4	1.372 (5)	C13A—H13C	0.9600
C5—H5	0.9300	C13B—H13D	0.9600
C7—C11	1.517 (5)	C13B—H13E	0.9600
C7—H7	0.9800	C13B—H13F	0.9600
C4—C3	1.387 (5)	C10—H10A	0.9600
C4—C12	1.518 (5)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600

C9—O1—C1	120.9 (2)	O4A—N3A—O5A	114.3 (8)
C6—C1—C2	122.1 (3)	O4A—N3A—C11	118.5 (9)
C6—C1—O1	122.2 (3)	O5A—N3A—C11	126.8 (8)
C2—C1—O1	115.7 (3)	O4B—N3B—O5B	118.9 (19)
N2—C8—C9	120.1 (3)	O4B—N3B—C11	128.9 (19)
N2—C8—C7	117.6 (2)	O5B—N3B—C11	112.1 (11)
C9—C8—C7	122.2 (3)	C13B—C12—C13A	53.2 (7)
O3—N2—O2	119.8 (3)	C13B—C12—C4	110.9 (5)
O3—N2—C8	118.7 (2)	C13A—C12—C4	116.9 (5)
O2—N2—C8	121.5 (3)	C13B—C12—H12A	141.0
N1—C9—O1	113.2 (3)	C13A—C12—H12A	108.1
N1—C9—C8	126.7 (3)	C4—C12—H12A	108.1
O1—C9—C8	120.1 (3)	C13B—C12—H12B	59.8
C9—N1—C10	125.0 (3)	C13A—C12—H12B	108.1
C9—N1—H1	117.5	C4—C12—H12B	108.1
C10—N1—H1	117.5	H12A—C12—H12B	107.3
C1—C6—C5	117.5 (3)	C13B—C12—H12C	109.5
C1—C6—C7	120.6 (3)	C13A—C12—H12C	57.4
C5—C6—C7	121.8 (3)	C4—C12—H12C	109.5
C3—C2—C1	118.7 (3)	H12A—C12—H12C	56.1
C3—C2—H2	120.6	H12B—C12—H12C	142.2
C1—C2—H2	120.6	C13B—C12—H12D	109.5
C4—C5—C6	122.2 (3)	C13A—C12—H12D	133.6
C4—C5—H5	118.9	C4—C12—H12D	109.5
C6—C5—H5	118.9	H12A—C12—H12D	55.3
C8—C7—C6	111.4 (2)	H12B—C12—H12D	53.9
C8—C7—C11	114.3 (3)	H12C—C12—H12D	108.0
C6—C7—C11	111.6 (3)	C12—C13A—H13A	109.5
C8—C7—H7	106.3	C12—C13A—H13B	109.5
C6—C7—H7	106.3	H13A—C13A—H13B	109.5
C11—C7—H7	106.3	C12—C13A—H13C	109.5
C5—C4—C3	118.2 (3)	H13A—C13A—H13C	109.5
C5—C4—C12	119.3 (3)	H13B—C13A—H13C	109.5
C3—C4—C12	122.5 (3)	C12—C13B—H13D	109.5
C2—C3—C4	121.4 (3)	C12—C13B—H13E	109.5
C2—C3—H3	119.3	H13D—C13B—H13E	109.5
C4—C3—H3	119.3	C12—C13B—H13F	109.5
N3B—C11—C7	114.4 (6)	H13D—C13B—H13F	109.5
N3A—C11—C7	111.4 (4)	H13E—C13B—H13F	109.5
N3B—C11—H11A	117.3	N1—C10—H10A	109.5
N3A—C11—H11A	109.3	N1—C10—H10B	109.5
C7—C11—H11A	109.3	H10A—C10—H10B	109.5
N3B—C11—H11B	97.5	N1—C10—H10C	109.5
N3A—C11—H11B	109.3	H10A—C10—H10C	109.5
C7—C11—H11B	109.3	H10B—C10—H10C	109.5
H11A—C11—H11B	108.0

C9—O1—C1—C6	7.7 (5)	C1—C6—C7—C8	−14.8 (4)
C9—O1—C1—C2	−172.0 (3)	C5—C6—C7—C8	168.7 (3)
C9—C8—N2—O3	179.8 (3)	C1—C6—C7—C11	114.3 (3)
C7—C8—N2—O3	2.4 (4)	C5—C6—C7—C11	−62.2 (4)
C9—C8—N2—O2	−0.7 (5)	C6—C5—C4—C3	−0.6 (5)
C7—C8—N2—O2	−178.2 (3)	C6—C5—C4—C12	177.5 (3)
C1—O1—C9—N1	174.0 (3)	C1—C2—C3—C4	0.0 (5)
C1—O1—C9—C8	−6.3 (4)	C5—C4—C3—C2	0.4 (6)
N2—C8—C9—N1	−4.2 (5)	C12—C4—C3—C2	−177.5 (4)
C7—C8—C9—N1	173.1 (3)	C8—C7—C11—N3B	59.4 (9)
N2—C8—C9—O1	176.1 (3)	C6—C7—C11—N3B	−68.2 (9)
C7—C8—C9—O1	−6.6 (5)	C8—C7—C11—N3A	72.3 (5)
O1—C9—N1—C10	−1.1 (5)	C6—C7—C11—N3A	−55.3 (5)
C8—C9—N1—C10	179.2 (4)	N3B—C11—N3A—O4A	65 (4)
C2—C1—C6—C5	0.3 (5)	C7—C11—N3A—O4A	−41.2 (12)
O1—C1—C6—C5	−179.4 (3)	N3B—C11—N3A—O5A	−123 (4)
C2—C1—C6—C7	−176.3 (3)	C7—C11—N3A—O5A	131.0 (10)
O1—C1—C6—C7	4.0 (5)	N3A—C11—N3B—O4B	−64 (4)
C6—C1—C2—C3	−0.4 (5)	C7—C11—N3B—O4B	15 (2)
O1—C1—C2—C3	179.3 (3)	N3A—C11—N3B—O5B	112 (4)
C1—C6—C5—C4	0.2 (5)	C7—C11—N3B—O5B	−169.6 (13)
C7—C6—C5—C4	176.8 (3)	C5—C4—C12—C13B	96.2 (7)
N2—C8—C7—C6	−166.3 (3)	C3—C4—C12—C13B	−85.9 (8)
C9—C8—C7—C6	16.4 (4)	C5—C4—C12—C13A	154.5 (7)
N2—C8—C7—C11	66.0 (4)	C3—C4—C12—C13A	−27.5 (8)
C9—C8—C7—C11	−111.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.600 (3)	129
N1—H1···O2ⁱ	0.86	2.21	2.943 (4)	143
C11—H11A···O3ⁱⁱ	0.97	2.58	3.258 (4)	128
C12—H12A···O2ⁱⁱⁱ	0.97	2.55	3.457 (5)	156

Symmetry codes: (i) −x+1, −y+1, −z+3; (ii) −x+2, −y+1, −z+2; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅N₃O₅
M_r	293.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2538 (10), 9.0431 (9), 10.3323 (12)
α, β, γ (°)	73.484 (9), 71.728 (11), 83.234 (9)
V (Å³)	701.75 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.4 × 0.35 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	4281, 2463, 1520
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.232, 1.06
No. of reflections	2463
No. of parameters	205
No. of restraints	122
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.34

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.600 (3)	129
N1—H1···O2ⁱ	0.86	2.21	2.943 (4)	143
C11—H11A···O3ⁱⁱ	0.97	2.58	3.258 (4)	128
C12—H12A···O2ⁱⁱⁱ	0.97	2.55	3.457 (5)	156

Symmetry codes: (i) −x+1, −y+1, −z+3; (ii) −x+2, −y+1, −z+2; (iii) x, y, z−1.

Footnotes

‡Additional correspondence author, e-mail: hspr@yahoo.com.

Acknowledgements

JM thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF). RK thanks the Centre for Bioinformatics (funded by the Department of Biotechnology and Department of Information Technology, New Delhi, India), Pondicherry University, for providing the computational facilities to carry out this research work. AP thanks Pondicherry University for a fellowship. HSPR thanks the UGC (University Grant Commission) for the Special Assistance Programme (SAP) and the Department of Science and Technology (DST) for the Fund for Improvement of Science and Technology Infrastructure in Universities and Higher Educational Institutions (FIST).

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