2-Methyl-3-nitro-N-{(E)-[5-(4-nitro-phen-yl)furan-2-yl]methyl-idene}aniline.

In the title Schiff-base type compound, C(18)H(13)N(3)O(5), the central furan ring makes dihedral angles of 12.80 (7) and 51.43 (4)° with the terminal benzene rings. The dihedral angle between the benzene rings is 45.43 (3)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (010). In addition, there are π-π stacking inter-actions within the layer [centroid-centroid distance = 3.584 (1) Å] and between the layers [centroid-centroid distance 3.751 (1) Å].

Related literature

For similar Schiff bases, see: Yamada et al. (2002 ▶); Cukurovali et al. (2002 ▶); Isloor et al. (2009 ▶); Abu Thaher et al. (2012 ▶). For the biological activity of Schiff bases, see: Vijesh et al. (2010 ▶); Tarafder et al. (2002 ▶); Ghorab et al. (2010 ▶); Ali et al. (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H13N3O5

M = 351.31

Monoclinic,

a = 10.9026 (3) Å

b = 10.2798 (3) Å

c = 14.2962 (3) Å

β = 101.529 (2)°

V = 1569.94 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.93 mm−1

T = 123 K

0.50 × 0.40 × 0.40 mm

Data collection

Oxford Diffraction Gemini-R diffractometer

Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007 ▶), and Clark & Reid (1995 ▶)] T min = 0.671, T max = 0.688

6460 measured reflections

3171 independent reflections

2764 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.05

3171 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033818/gk2492sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033818/gk2492Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033818/gk2492Isup3.cml

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

C18H13N3O5	F(000) = 728
Mr = 351.31	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 3039 reflections
a = 10.9026 (3) Å	θ = 3.2–75.5°
b = 10.2798 (3) Å	µ = 0.93 mm−1
c = 14.2962 (3) Å	T = 123 K
β = 101.529 (2)°	Block, light yellow
V = 1569.94 (7) Å3	0.50 × 0.40 × 0.40 mm
Z = 4

Oxford Diffraction Gemini-R diffractometer	3171 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2764 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 4.1°
ω scans	h = −12→13
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007), and Clark & Reid (1995)]	k = −12→12
Tmin = 0.671, Tmax = 0.688	l = −17→7
6460 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.3233P] where P = (Fo2 + 2Fc2)/3
3171 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
N1	−0.22774 (12)	0.22828 (14)	−0.24867 (10)	0.0309 (3)
N2	0.28795 (11)	0.40005 (12)	0.30426 (9)	0.0224 (3)
N3	0.26983 (13)	0.41136 (13)	0.64618 (9)	0.0281 (3)
O1	−0.32515 (11)	0.21084 (14)	−0.21964 (10)	0.0412 (3)
O2	−0.21821 (12)	0.20872 (15)	−0.33171 (9)	0.0448 (3)
O3	0.20668 (9)	0.40126 (10)	0.10398 (7)	0.0206 (2)
O4	0.15778 (13)	0.43153 (18)	0.63095 (9)	0.0537 (4)
O5	0.33489 (12)	0.41218 (14)	0.72703 (8)	0.0403 (3)
C1	−0.11759 (13)	0.27566 (15)	−0.18146 (10)	0.0247 (3)
C2	−0.01288 (15)	0.31134 (16)	−0.21649 (11)	0.0280 (3)
H2A	−0.0121	0.3041	−0.2812	0.034*
C3	0.09029 (14)	0.35784 (16)	−0.15327 (10)	0.0258 (3)
H3A	0.1611	0.3832	−0.1756	0.031*
C4	0.08916 (13)	0.36719 (14)	−0.05598 (10)	0.0209 (3)
C5	−0.01791 (13)	0.32932 (14)	−0.02242 (10)	0.0224 (3)
H5A	−0.0187	0.3345	0.0424	0.027*
C6	−0.12221 (13)	0.28430 (14)	−0.08556 (11)	0.0242 (3)
H6A	−0.1940	0.2603	−0.0641	0.029*
C7	0.20003 (13)	0.41645 (14)	0.00792 (10)	0.0204 (3)
C8	0.30432 (14)	0.47801 (15)	−0.00873 (10)	0.0236 (3)
H8A	0.3217	0.4999	−0.0679	0.028*
C9	0.38082 (14)	0.50202 (15)	0.08172 (10)	0.0236 (3)
H9A	0.4585	0.5428	0.0936	0.028*
C10	0.31886 (13)	0.45401 (14)	0.14813 (10)	0.0215 (3)
C11	0.35804 (13)	0.44480 (14)	0.25000 (10)	0.0222 (3)
H11A	0.4382	0.4727	0.2778	0.027*
C12	0.34377 (13)	0.38033 (14)	0.40136 (10)	0.0216 (3)
C13	0.46195 (14)	0.32360 (15)	0.42596 (11)	0.0248 (3)
H13A	0.5056	0.3028	0.3783	0.030*
C14	0.51519 (14)	0.29778 (15)	0.52044 (11)	0.0270 (3)
H14A	0.5945	0.2608	0.5361	0.032*
C15	0.45026 (14)	0.32705 (15)	0.59109 (10)	0.0248 (3)
H15A	0.4849	0.3099	0.6548	0.030*
C16	0.33171 (13)	0.38282 (14)	0.56546 (10)	0.0221 (3)
C17	0.27330 (13)	0.41176 (14)	0.47145 (10)	0.0208 (3)
C18	0.14791 (14)	0.47584 (16)	0.43966 (11)	0.0267 (3)
H18A	0.1486	0.5596	0.4694	0.040*
H18B	0.0841	0.4227	0.4577	0.040*
H18C	0.1310	0.4861	0.3715	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0263 (7)	0.0291 (7)	0.0333 (7)	0.0015 (5)	−0.0037 (5)	−0.0025 (6)
N2	0.0224 (6)	0.0234 (6)	0.0213 (6)	0.0002 (5)	0.0040 (5)	−0.0015 (5)
N3	0.0339 (7)	0.0280 (7)	0.0237 (6)	−0.0029 (6)	0.0091 (5)	0.0007 (5)
O1	0.0234 (6)	0.0482 (8)	0.0492 (7)	−0.0046 (5)	0.0003 (5)	−0.0067 (6)
O2	0.0407 (7)	0.0580 (9)	0.0306 (6)	−0.0050 (6)	−0.0051 (5)	−0.0087 (6)
O3	0.0211 (5)	0.0228 (5)	0.0177 (5)	−0.0007 (4)	0.0034 (4)	−0.0005 (4)
O4	0.0355 (7)	0.0957 (13)	0.0336 (7)	0.0182 (8)	0.0155 (5)	0.0061 (7)
O5	0.0425 (7)	0.0572 (8)	0.0218 (6)	−0.0081 (6)	0.0076 (5)	−0.0048 (5)
C1	0.0221 (7)	0.0231 (7)	0.0263 (7)	0.0025 (6)	−0.0015 (6)	−0.0012 (6)
C2	0.0282 (7)	0.0338 (8)	0.0212 (7)	0.0010 (6)	0.0031 (6)	−0.0012 (6)
C3	0.0238 (7)	0.0314 (8)	0.0230 (7)	0.0001 (6)	0.0067 (5)	0.0022 (6)
C4	0.0213 (7)	0.0194 (7)	0.0215 (7)	0.0028 (5)	0.0031 (5)	0.0013 (5)
C5	0.0234 (7)	0.0221 (7)	0.0220 (7)	0.0029 (6)	0.0056 (5)	0.0008 (6)
C6	0.0209 (7)	0.0226 (7)	0.0295 (8)	0.0024 (6)	0.0061 (6)	0.0025 (6)
C7	0.0229 (7)	0.0206 (7)	0.0182 (7)	0.0043 (5)	0.0051 (5)	0.0020 (5)
C8	0.0234 (7)	0.0265 (7)	0.0218 (7)	0.0022 (6)	0.0064 (5)	0.0030 (6)
C9	0.0212 (7)	0.0245 (7)	0.0254 (7)	−0.0009 (6)	0.0052 (5)	0.0004 (6)
C10	0.0190 (6)	0.0206 (7)	0.0247 (7)	−0.0002 (5)	0.0043 (5)	−0.0011 (6)
C11	0.0217 (7)	0.0208 (7)	0.0239 (7)	−0.0005 (6)	0.0038 (5)	−0.0022 (6)
C12	0.0229 (7)	0.0211 (7)	0.0205 (7)	−0.0037 (6)	0.0037 (5)	−0.0014 (5)
C13	0.0246 (7)	0.0262 (7)	0.0246 (7)	0.0001 (6)	0.0073 (6)	−0.0020 (6)
C14	0.0226 (7)	0.0270 (8)	0.0299 (8)	0.0025 (6)	0.0016 (6)	−0.0013 (6)
C15	0.0271 (7)	0.0234 (7)	0.0219 (7)	−0.0036 (6)	−0.0001 (5)	0.0000 (6)
C16	0.0254 (7)	0.0205 (7)	0.0215 (7)	−0.0050 (6)	0.0069 (5)	−0.0023 (5)
C17	0.0204 (7)	0.0189 (7)	0.0236 (7)	−0.0033 (5)	0.0053 (5)	−0.0012 (5)
C18	0.0237 (7)	0.0295 (8)	0.0270 (7)	0.0022 (6)	0.0056 (6)	0.0001 (6)

N1—O1	1.2282 (18)	C7—C8	1.363 (2)
N1—O2	1.2288 (19)	C8—C9	1.413 (2)
N1—C1	1.4633 (19)	C8—H8A	0.9300
N2—C11	1.2783 (19)	C9—C10	1.363 (2)
N2—C12	1.4145 (18)	C9—H9A	0.9300
N3—O4	1.2151 (19)	C10—C11	1.437 (2)
N3—O5	1.2294 (18)	C11—H11A	0.9300
N3—C16	1.4779 (18)	C12—C13	1.394 (2)
O3—C7	1.3696 (16)	C12—C17	1.417 (2)
O3—C10	1.3711 (17)	C13—C14	1.385 (2)
C1—C2	1.385 (2)	C13—H13A	0.9300
C1—C6	1.385 (2)	C14—C15	1.378 (2)
C2—C3	1.380 (2)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.394 (2)
C3—C4	1.397 (2)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.399 (2)
C4—C5	1.403 (2)	C17—C18	1.504 (2)
C4—C7	1.453 (2)	C18—H18A	0.9600
C5—C6	1.383 (2)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—H6A	0.9300
O1—N1—O2	123.25 (14)	C10—C9—H9A	126.6
O1—N1—C1	118.58 (14)	C8—C9—H9A	126.6
O2—N1—C1	118.17 (14)	C9—C10—O3	110.08 (12)
C11—N2—C12	117.06 (12)	C9—C10—C11	129.92 (13)
O4—N3—O5	122.54 (14)	O3—C10—C11	119.85 (12)
O4—N3—C16	119.57 (13)	N2—C11—C10	123.11 (13)
O5—N3—C16	117.89 (13)	N2—C11—H11A	118.4
C7—O3—C10	106.26 (11)	C10—C11—H11A	118.4
C2—C1—C6	122.47 (14)	C13—C12—N2	120.15 (13)
C2—C1—N1	118.59 (14)	C13—C12—C17	121.44 (13)
C6—C1—N1	118.94 (14)	N2—C12—C17	118.28 (13)
C3—C2—C1	118.55 (14)	C14—C13—C12	120.82 (14)
C3—C2—H2A	120.7	C14—C13—H13A	119.6
C1—C2—H2A	120.7	C12—C13—H13A	119.6
C2—C3—C4	120.52 (14)	C15—C14—C13	119.77 (14)
C2—C3—H3A	119.7	C15—C14—H14A	120.1
C4—C3—H3A	119.7	C13—C14—H14A	120.1
C3—C4—C5	119.67 (13)	C14—C15—C16	118.84 (14)
C3—C4—C7	118.58 (13)	C14—C15—H15A	120.6
C5—C4—C7	121.76 (13)	C16—C15—H15A	120.6
C6—C5—C4	120.11 (13)	C15—C16—C17	124.04 (14)
C6—C5—H5A	119.9	C15—C16—N3	114.85 (13)
C4—C5—H5A	119.9	C17—C16—N3	121.10 (13)
C5—C6—C1	118.68 (14)	C16—C17—C12	115.08 (13)
C5—C6—H6A	120.7	C16—C17—C18	126.53 (13)
C1—C6—H6A	120.7	C12—C17—C18	118.35 (13)
C8—C7—O3	110.44 (13)	C17—C18—H18A	109.5
C8—C7—C4	132.08 (13)	C17—C18—H18B	109.5
O3—C7—C4	117.48 (12)	H18A—C18—H18B	109.5
C7—C8—C9	106.36 (13)	C17—C18—H18C	109.5
C7—C8—H8A	126.8	H18A—C18—H18C	109.5
C9—C8—H8A	126.8	H18B—C18—H18C	109.5
C10—C9—C8	106.86 (13)
O1—N1—C1—C2	−171.75 (15)	C7—O3—C10—C9	0.44 (15)
O2—N1—C1—C2	7.8 (2)	C7—O3—C10—C11	−175.51 (13)
O1—N1—C1—C6	7.7 (2)	C12—N2—C11—C10	171.79 (14)
O2—N1—C1—C6	−172.80 (15)	C9—C10—C11—N2	178.09 (15)
C6—C1—C2—C3	−0.3 (2)	O3—C10—C11—N2	−6.9 (2)
N1—C1—C2—C3	179.05 (14)	C11—N2—C12—C13	−43.4 (2)
C1—C2—C3—C4	0.7 (2)	C11—N2—C12—C17	140.62 (14)
C2—C3—C4—C5	−0.2 (2)	N2—C12—C13—C14	−176.78 (14)
C2—C3—C4—C7	179.87 (14)	C17—C12—C13—C14	−0.9 (2)
C3—C4—C5—C6	−0.7 (2)	C12—C13—C14—C15	0.7 (2)
C7—C4—C5—C6	179.25 (13)	C13—C14—C15—C16	−0.2 (2)
C4—C5—C6—C1	1.0 (2)	C14—C15—C16—C17	−0.1 (2)
C2—C1—C6—C5	−0.5 (2)	C14—C15—C16—N3	−179.66 (13)
N1—C1—C6—C5	−179.91 (13)	O4—N3—C16—C15	−163.26 (16)
C10—O3—C7—C8	−0.50 (15)	O5—N3—C16—C15	15.9 (2)
C10—O3—C7—C4	179.55 (12)	O4—N3—C16—C17	17.2 (2)
C3—C4—C7—C8	12.5 (2)	O5—N3—C16—C17	−163.65 (14)
C5—C4—C7—C8	−167.42 (15)	C15—C16—C17—C12	−0.1 (2)
C3—C4—C7—O3	−167.53 (13)	N3—C16—C17—C12	179.45 (12)
C5—C4—C7—O3	12.5 (2)	C15—C16—C17—C18	−177.78 (14)
O3—C7—C8—C9	0.36 (17)	N3—C16—C17—C18	1.8 (2)
C4—C7—C8—C9	−179.70 (15)	C13—C12—C17—C16	0.6 (2)
C7—C8—C9—C10	−0.08 (17)	N2—C12—C17—C16	176.52 (12)
C8—C9—C10—O3	−0.23 (17)	C13—C12—C17—C18	178.50 (14)
C8—C9—C10—C11	175.19 (15)	N2—C12—C17—C18	−5.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···N2	0.96	2.30	2.8047 (19)	112
C3—H3A···O5i	0.93	2.58	3.4895 (19)	165
C13—H13A···O1ii	0.93	2.53	3.432 (2)	162
C14—H14A···O2iii	0.93	2.55	3.361 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O5i	0.93	2.58	3.4895 (19)	165
C13—H13A⋯O1ii	0.93	2.53	3.432 (2)	162
C14—H14A⋯O2iii	0.93	2.55	3.361 (2)	147

Symmetry codes: (i) ; (ii) ; (iii) .