Ethyl 3-nitro-4-(propyl-amino)benzoate.

In the title compound, C(12)H(16)N(2)O(4), intra-molecular N-H⋯O and C-H⋯O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The nitro group is almost coplanar with the benzene ring, forming a dihedral angle of 6.2 (2)°. In the crystal structure, neighbouring mol-ecules are linked together by inter-molecular N-H⋯O and O⋯O inter-actions. Of interest are the short inter-molecular O⋯O inter-actions which cause a stacking arrangement of the mol-ecules along the a axis.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Ishida et al. (2006 ▶); Vinodkumar et al. (2008 ▶). Rida et al. (2005 ▶); Harikrishnan et al. (2008 ▶); Moore et al. (2005 ▶).

Experimental

Crystal data

C12H16N2O4

M = 252.27

Triclinic,

a = 4.4914 (4) Å

b = 12.0828 (9) Å

c = 12.8763 (9) Å

α = 62.494 (4)°

β = 81.055 (4)°

γ = 83.494 (4)°

V = 611.57 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.51 × 0.26 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.949, T max = 0.974

12286 measured reflections

2372 independent reflections

1946 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.252

S = 1.17

2372 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021314/at2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021314/at2590Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H16N2O4	Z = 2
Mr = 252.27	F000 = 268
Triclinic, P1	Dx = 1.370 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.4914 (4) Å	Cell parameters from 6896 reflections
b = 12.0828 (9) Å	θ = 3.2–33.0º
c = 12.8763 (9) Å	µ = 0.10 mm−1
α = 62.494 (4)º	T = 100.0 (1) K
β = 81.055 (4)º	Needle, yellow
γ = 83.494 (4)º	0.51 × 0.26 × 0.26 mm
V = 611.57 (8) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2372 independent reflections
Radiation source: fine-focus sealed tube	1946 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 100.0(1) K	θmax = 26.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −5→5
Tmin = 0.949, Tmax = 0.974	k = −14→14
12286 measured reflections	l = −15→15

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)] = 0.076	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.252	w = 1/[σ2(Fo2) + (0.1098P)2 + 1.609P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
2372 reflections	Δρmax = 0.47 e Å−3
169 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
O1	0.2464 (7)	0.4136 (3)	0.5558 (2)	0.0326 (7)
O2	0.5971 (6)	0.2725 (2)	0.6301 (2)	0.0316 (7)
O3	0.8766 (6)	0.1455 (2)	1.0099 (2)	0.0239 (6)
O4	0.7178 (6)	0.2578 (2)	1.1092 (2)	0.0272 (6)
N1	0.0274 (7)	0.5600 (3)	0.6530 (3)	0.0217 (7)
N2	0.4117 (7)	0.3535 (3)	0.6346 (3)	0.0228 (7)
C1	0.3823 (8)	0.3799 (3)	0.7345 (3)	0.0195 (7)
C2	0.5528 (8)	0.3013 (3)	0.8258 (3)	0.0200 (7)
H2A	0.6775	0.2374	0.8192	0.024*
C3	0.5379 (8)	0.3177 (3)	0.9255 (3)	0.0200 (7)
C4	0.3490 (8)	0.4159 (3)	0.9327 (3)	0.0210 (7)
H4A	0.3358	0.4274	0.9999	0.025*
C5	0.1849 (8)	0.4945 (3)	0.8436 (3)	0.0215 (7)
H5A	0.0650	0.5589	0.8512	0.026*
C6	0.1917 (8)	0.4809 (3)	0.7389 (3)	0.0203 (7)
C7	−0.1636 (8)	0.6655 (3)	0.6552 (3)	0.0223 (7)
H7A	−0.2755	0.6388	0.7330	0.027*
H7B	−0.3086	0.6895	0.5991	0.027*
C8	0.0108 (8)	0.7792 (3)	0.6262 (3)	0.0238 (8)
H8A	0.1518	0.7572	0.6834	0.029*
H8B	0.1251	0.8065	0.5488	0.029*
C9	−0.2061 (9)	0.8850 (3)	0.6280 (3)	0.0281 (8)
H9A	−0.0932	0.9532	0.6169	0.042*
H9B	−0.3304	0.8557	0.7025	0.042*
H9C	−0.3313	0.9126	0.5657	0.042*
C10	0.7166 (8)	0.2397 (3)	1.0240 (3)	0.0212 (7)
C11	1.0559 (8)	0.0633 (3)	1.1042 (3)	0.0253 (8)
H11A	1.1345	0.1115	1.1358	0.030*
H11B	1.2257	0.0261	1.0728	0.030*
C12	0.8678 (9)	−0.0386 (3)	1.2015 (3)	0.0292 (8)
H12A	0.9926	−0.0943	1.2607	0.044*
H12B	0.7837	−0.0843	1.1696	0.044*
H12C	0.7077	−0.0020	1.2361	0.044*
H1N1	0.031 (11)	0.547 (4)	0.593 (5)	0.038 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0432 (16)	0.0348 (15)	0.0271 (14)	0.0142 (12)	−0.0198 (12)	−0.0189 (12)
O2	0.0420 (16)	0.0317 (14)	0.0240 (14)	0.0155 (12)	−0.0099 (11)	−0.0171 (11)
O3	0.0281 (13)	0.0254 (13)	0.0187 (12)	0.0036 (10)	−0.0072 (10)	−0.0099 (10)
O4	0.0372 (15)	0.0284 (13)	0.0185 (12)	0.0009 (11)	−0.0075 (10)	−0.0120 (11)
N1	0.0265 (16)	0.0218 (14)	0.0198 (15)	0.0033 (12)	−0.0064 (12)	−0.0117 (12)
N2	0.0290 (16)	0.0206 (14)	0.0189 (14)	0.0030 (12)	−0.0069 (12)	−0.0087 (12)
C1	0.0248 (17)	0.0185 (16)	0.0145 (16)	−0.0023 (13)	−0.0022 (13)	−0.0065 (13)
C2	0.0232 (17)	0.0182 (15)	0.0186 (16)	−0.0010 (13)	−0.0024 (13)	−0.0084 (13)
C3	0.0211 (17)	0.0211 (16)	0.0170 (16)	−0.0035 (13)	−0.0014 (13)	−0.0077 (13)
C4	0.0275 (18)	0.0212 (16)	0.0143 (15)	−0.0045 (13)	−0.0003 (13)	−0.0080 (13)
C5	0.0228 (17)	0.0216 (16)	0.0201 (17)	−0.0017 (13)	−0.0005 (13)	−0.0100 (14)
C6	0.0200 (16)	0.0200 (16)	0.0199 (17)	−0.0032 (13)	−0.0015 (13)	−0.0080 (13)
C7	0.0235 (17)	0.0215 (17)	0.0219 (17)	0.0052 (13)	−0.0060 (13)	−0.0101 (14)
C8	0.0248 (18)	0.0235 (17)	0.0215 (17)	0.0016 (14)	−0.0030 (13)	−0.0094 (14)
C9	0.033 (2)	0.0240 (18)	0.0261 (19)	0.0008 (15)	−0.0019 (15)	−0.0112 (15)
C10	0.0228 (17)	0.0204 (16)	0.0188 (16)	−0.0036 (13)	−0.0012 (13)	−0.0074 (13)
C11	0.0249 (18)	0.0290 (18)	0.0208 (17)	0.0048 (14)	−0.0080 (14)	−0.0101 (15)
C12	0.034 (2)	0.0262 (18)	0.0247 (19)	0.0051 (15)	−0.0066 (15)	−0.0101 (15)

O1—N2	1.241 (4)	C5—C6	1.426 (5)
O2—N2	1.228 (4)	C5—H5A	0.9300
O3—C10	1.345 (4)	C7—C8	1.524 (5)
O3—C11	1.455 (4)	C7—H7A	0.9700
O4—C10	1.214 (4)	C7—H7B	0.9700
N1—C6	1.342 (4)	C8—C9	1.523 (5)
N1—C7	1.462 (4)	C8—H8A	0.9700
N1—H1N1	0.86 (5)	C8—H8B	0.9700
N2—C1	1.445 (4)	C9—H9A	0.9600
C1—C2	1.398 (5)	C9—H9B	0.9600
C1—C6	1.428 (5)	C9—H9C	0.9600
C2—C3	1.378 (5)	C11—C12	1.511 (5)
C2—H2A	0.9300	C11—H11A	0.9700
C3—C4	1.409 (5)	C11—H11B	0.9700
C3—C10	1.477 (5)	C12—H12A	0.9600
C4—C5	1.364 (5)	C12—H12B	0.9600
C4—H4A	0.9300	C12—H12C	0.9600
O1···O1i	2.914 (5)	O1···O1ii	2.984 (5)
C10—O3—C11	116.1 (3)	C8—C7—H7B	108.8
C6—N1—C7	125.0 (3)	H7A—C7—H7B	107.7
C6—N1—H1N1	118 (3)	C9—C8—C7	110.2 (3)
C7—N1—H1N1	117 (3)	C9—C8—H8A	109.6
O2—N2—O1	121.8 (3)	C7—C8—H8A	109.6
O2—N2—C1	119.5 (3)	C9—C8—H8B	109.6
O1—N2—C1	118.6 (3)	C7—C8—H8B	109.6
C2—C1—C6	122.1 (3)	H8A—C8—H8B	108.1
C2—C1—N2	116.1 (3)	C8—C9—H9A	109.5
C6—C1—N2	121.8 (3)	C8—C9—H9B	109.5
C3—C2—C1	120.6 (3)	H9A—C9—H9B	109.5
C3—C2—H2A	119.7	C8—C9—H9C	109.5
C1—C2—H2A	119.7	H9A—C9—H9C	109.5
C2—C3—C4	118.4 (3)	H9B—C9—H9C	109.5
C2—C3—C10	123.3 (3)	O4—C10—O3	123.5 (3)
C4—C3—C10	118.2 (3)	O4—C10—C3	123.7 (3)
C5—C4—C3	121.6 (3)	O3—C10—C3	112.8 (3)
C5—C4—H4A	119.2	O3—C11—C12	110.8 (3)
C3—C4—H4A	119.2	O3—C11—H11A	109.5
C4—C5—C6	122.0 (3)	C12—C11—H11A	109.5
C4—C5—H5A	119.0	O3—C11—H11B	109.5
C6—C5—H5A	119.0	C12—C11—H11B	109.5
N1—C6—C5	120.4 (3)	H11A—C11—H11B	108.1
N1—C6—C1	124.4 (3)	C11—C12—H12A	109.5
C5—C6—C1	115.2 (3)	C11—C12—H12B	109.5
N1—C7—C8	113.8 (3)	H12A—C12—H12B	109.5
N1—C7—H7A	108.8	C11—C12—H12C	109.5
C8—C7—H7A	108.8	H12A—C12—H12C	109.5
N1—C7—H7B	108.8	H12B—C12—H12C	109.5
O2—N2—C1—C2	−5.7 (5)	C4—C5—C6—C1	−0.1 (5)
O1—N2—C1—C2	174.0 (3)	C2—C1—C6—N1	178.9 (3)
O2—N2—C1—C6	173.9 (3)	N2—C1—C6—N1	−0.5 (5)
O1—N2—C1—C6	−6.5 (5)	C2—C1—C6—C5	−0.9 (5)
C6—C1—C2—C3	1.2 (5)	N2—C1—C6—C5	179.6 (3)
N2—C1—C2—C3	−179.2 (3)	C6—N1—C7—C8	78.2 (4)
C1—C2—C3—C4	−0.5 (5)	N1—C7—C8—C9	178.8 (3)
C1—C2—C3—C10	−178.7 (3)	C11—O3—C10—O4	0.3 (5)
C2—C3—C4—C5	−0.5 (5)	C11—O3—C10—C3	−179.2 (3)
C10—C3—C4—C5	177.8 (3)	C2—C3—C10—O4	175.7 (3)
C3—C4—C5—C6	0.9 (5)	C4—C3—C10—O4	−2.5 (5)
C7—N1—C6—C5	1.2 (5)	C2—C3—C10—O3	−4.8 (5)
C7—N1—C6—C1	−178.6 (3)	C4—C3—C10—O3	177.0 (3)
C4—C5—C6—N1	180.0 (3)	C10—O3—C11—C12	85.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.85 (5)	2.00 (6)	2.633 (5)	131 (5)
N1—H1N1···O1i	0.85 (5)	2.28 (5)	2.998 (4)	141 (5)
C2—H2A···O2	0.93	2.35	2.674 (4)	100

Table 1

Selected interatomic distances (Å)

O1⋯O1i	2.914 (5)
O1⋯O1ii	2.984 (5)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.85 (5)	2.00 (6)	2.633 (5)	131 (5)
N1—H1N1⋯O1i	0.85 (5)	2.28 (5)	2.998 (4)	141 (5)
C2—H2A⋯O2	0.93	2.35	2.674 (4)	100

Symmetry code: (i) .