Crystal structure of 2-cyano-N-(furan-2-ylmeth-yl)-3-(3-nitro-phen-yl)propanamide.

In the title compound, C15H11N3O4, the acetamide group is inclined to the furan ring by 66.5 (1)°. The dihedral angle between the furan ring and the benzene ring is 66.8 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. The dimers are linked via two pairs of C-H⋯O hydrogen bonds to the same acceptor oxygen atom, enclosing R 2 (1)(6) ring motifs, forming chains along the [101] direction.

Related literature

For examples of biological properties of furan derivatives, see: Anupam et al. (2011 ▸). For the biological activities of some heterocyclic derivatives containing the acetamide moiety, see: Fallah-Tafti et al. (2011 ▸); Shams et al. (2011 ▸). For the crystal structure of the similar compound 2-cyano-N-furfuryl-3-(2-fur­yl)acryl­amide, see: Pomés Hernández et al. (1996 ▸).

Experimental

Crystal data

C15H11N3O4

M = 297.27

Triclinic,

a = 7.4358 (3) Å

b = 9.4165 (5) Å

c = 10.3934 (5) Å

α = 90.938 (2)°

β = 96.910 (2)°

γ = 105.872 (2)°

V = 693.98 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.942, T max = 0.983

12708 measured reflections

2442 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.02

2442 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015012918/su5161sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012918/su5161Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012918/su5161Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012918/su5161fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015012918/su5161fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). For clarity, H atoms not involved in hydrogen bonding have been omitted.

CCDC reference: 1410650

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H11N3O4	Z = 2
Mr = 297.27	F(000) = 308
Triclinic, P1	Dx = 1.423 Mg m−3
a = 7.4358 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4165 (5) Å	Cell parameters from 6452 reflections
c = 10.3934 (5) Å	θ = 2.8–25.6°
α = 90.938 (2)°	µ = 0.11 mm−1
β = 96.910 (2)°	T = 293 K
γ = 105.872 (2)°	Block, colourless
V = 693.98 (6) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2442 independent reflections
Radiation source: fine-focus sealed tube	2055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.942, Tmax = 0.983	k = −11→10
12708 measured reflections	l = −12→12

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.059P)2 + 0.2005P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2442 reflections	Δρmax = 0.22 e Å−3
200 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (5)

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.

	x	y	z	Uiso*/Ueq
C1	0.5353 (2)	0.28891 (17)	0.58091 (15)	0.0437 (4)
H1	0.5862	0.3239	0.6654	0.052*
C2	0.6211 (2)	0.20823 (17)	0.51113 (16)	0.0450 (4)
C3	0.5534 (3)	0.15471 (19)	0.38555 (17)	0.0548 (5)
H3	0.6160	0.1015	0.3400	0.066*
C4	0.3898 (3)	0.1826 (2)	0.32955 (17)	0.0576 (5)
H4	0.3401	0.1470	0.2450	0.069*
C5	0.2988 (2)	0.26268 (18)	0.39767 (15)	0.0479 (4)
H5	0.1879	0.2798	0.3586	0.057*
C6	0.3703 (2)	0.31818 (16)	0.52382 (14)	0.0389 (4)
C7	0.2662 (2)	0.40380 (16)	0.58752 (14)	0.0392 (4)
H7	0.1617	0.4177	0.5360	0.047*
C8	0.2965 (2)	0.46539 (16)	0.70769 (14)	0.0380 (4)
C9	0.1628 (2)	0.54718 (17)	0.74909 (14)	0.0404 (4)
C10	0.0773 (2)	0.67695 (19)	0.92842 (16)	0.0486 (4)
H10A	0.0750	0.6564	1.0194	0.058*
H10B	−0.0509	0.6412	0.8851	0.058*
C11	0.1429 (2)	0.83840 (19)	0.91721 (15)	0.0474 (4)
C12	0.2518 (5)	0.9468 (3)	0.9961 (2)	0.1020 (10)
H12	0.3096	0.9378	1.0788	0.122*
C13	0.2647 (5)	1.0791 (3)	0.9319 (3)	0.1089 (10)
H13	0.3310	1.1739	0.9645	0.131*
C14	0.1663 (3)	1.0432 (3)	0.8186 (3)	0.0790 (7)
H14	0.1519	1.1094	0.7553	0.095*
C15	0.4516 (2)	0.45908 (19)	0.80123 (14)	0.0447 (4)
N1	0.7935 (2)	0.17794 (17)	0.57526 (18)	0.0592 (4)
N2	0.5728 (2)	0.4565 (2)	0.87857 (14)	0.0667 (5)
N3	0.19322 (18)	0.59563 (15)	0.87343 (12)	0.0439 (3)
H3A	0.2851	0.5781	0.9231	0.053*
O1	0.8792 (2)	0.1167 (2)	0.51177 (17)	0.0881 (5)
O2	0.8406 (2)	0.2139 (2)	0.69036 (16)	0.0840 (5)
O3	0.03619 (18)	0.56592 (15)	0.67145 (11)	0.0609 (4)
O4	0.0876 (2)	0.89464 (16)	0.80594 (13)	0.0724 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (9)	0.0476 (9)	0.0417 (8)	0.0195 (7)	0.0013 (7)	0.0035 (7)
C2	0.0437 (9)	0.0420 (9)	0.0556 (10)	0.0200 (7)	0.0106 (7)	0.0120 (7)
C3	0.0667 (11)	0.0488 (10)	0.0584 (11)	0.0261 (9)	0.0212 (9)	0.0027 (8)
C4	0.0688 (12)	0.0622 (11)	0.0452 (9)	0.0268 (9)	0.0017 (8)	−0.0086 (8)
C5	0.0490 (9)	0.0522 (10)	0.0439 (9)	0.0201 (8)	−0.0023 (7)	−0.0022 (7)
C6	0.0395 (8)	0.0396 (8)	0.0392 (8)	0.0148 (6)	0.0023 (6)	0.0039 (6)
C7	0.0376 (8)	0.0436 (8)	0.0381 (8)	0.0172 (7)	−0.0022 (6)	0.0032 (6)
C8	0.0375 (8)	0.0413 (8)	0.0369 (8)	0.0159 (6)	−0.0002 (6)	0.0053 (6)
C9	0.0415 (8)	0.0445 (9)	0.0379 (8)	0.0191 (7)	−0.0009 (6)	0.0030 (6)
C10	0.0509 (9)	0.0579 (10)	0.0426 (9)	0.0227 (8)	0.0099 (7)	0.0007 (7)
C11	0.0511 (9)	0.0554 (10)	0.0414 (8)	0.0257 (8)	0.0035 (7)	−0.0015 (7)
C12	0.159 (3)	0.0602 (14)	0.0657 (14)	0.0154 (15)	−0.0330 (15)	−0.0052 (11)
C13	0.153 (3)	0.0523 (14)	0.107 (2)	0.0143 (15)	−0.008 (2)	−0.0025 (13)
C14	0.0888 (16)	0.0643 (14)	0.0948 (17)	0.0370 (12)	0.0152 (13)	0.0253 (12)
C15	0.0470 (9)	0.0588 (10)	0.0342 (8)	0.0262 (8)	0.0012 (7)	−0.0008 (7)
N1	0.0539 (9)	0.0598 (9)	0.0764 (11)	0.0323 (8)	0.0161 (8)	0.0197 (8)
N2	0.0628 (10)	0.1065 (14)	0.0412 (8)	0.0480 (9)	−0.0084 (7)	−0.0060 (8)
N3	0.0474 (7)	0.0536 (8)	0.0364 (7)	0.0261 (6)	−0.0006 (5)	0.0010 (6)
O1	0.0840 (11)	0.1097 (13)	0.1024 (12)	0.0702 (10)	0.0338 (9)	0.0228 (9)
O2	0.0720 (10)	0.1099 (13)	0.0829 (11)	0.0555 (9)	−0.0105 (8)	0.0032 (9)
O3	0.0626 (8)	0.0875 (9)	0.0446 (6)	0.0495 (7)	−0.0111 (6)	−0.0084 (6)
O4	0.0791 (9)	0.0714 (9)	0.0649 (8)	0.0266 (7)	−0.0123 (7)	0.0114 (7)

C1—C2	1.367 (2)	C9—N3	1.3354 (19)
C1—C6	1.396 (2)	C10—N3	1.4564 (19)
C1—H1	0.9300	C10—C11	1.475 (2)
C2—C3	1.376 (2)	C10—H10A	0.9700
C2—N1	1.472 (2)	C10—H10B	0.9700
C3—C4	1.377 (3)	C11—C12	1.315 (3)
C3—H3	0.9300	C11—O4	1.346 (2)
C4—C5	1.380 (2)	C12—C13	1.408 (4)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.390 (2)	C13—C14	1.296 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.461 (2)	C14—O4	1.358 (3)
C7—C8	1.336 (2)	C14—H14	0.9300
C7—H7	0.9300	C15—N2	1.139 (2)
C8—C15	1.432 (2)	N1—O1	1.210 (2)
C8—C9	1.509 (2)	N1—O2	1.220 (2)
C9—O3	1.2170 (18)	N3—H3A	0.8600
C2—C1—C6	119.19 (15)	N3—C10—C11	114.03 (14)
C2—C1—H1	120.4	N3—C10—H10A	108.7
C6—C1—H1	120.4	C11—C10—H10A	108.7
C1—C2—C3	123.02 (15)	N3—C10—H10B	108.7
C1—C2—N1	117.60 (15)	C11—C10—H10B	108.7
C3—C2—N1	119.38 (15)	H10A—C10—H10B	107.6
C2—C3—C4	117.80 (15)	C12—C11—O4	109.03 (18)
C2—C3—H3	121.1	C12—C11—C10	132.98 (17)
C4—C3—H3	121.1	O4—C11—C10	117.98 (15)
C3—C4—C5	120.64 (16)	C11—C12—C13	107.3 (2)
C3—C4—H4	119.7	C11—C12—H12	126.4
C5—C4—H4	119.7	C13—C12—H12	126.4
C4—C5—C6	121.02 (15)	C14—C13—C12	106.8 (2)
C4—C5—H5	119.5	C14—C13—H13	126.6
C6—C5—H5	119.5	C12—C13—H13	126.6
C5—C6—C1	118.31 (14)	C13—C14—O4	109.9 (2)
C5—C6—C7	117.18 (13)	C13—C14—H14	125.0
C1—C6—C7	124.50 (13)	O4—C14—H14	125.0
C8—C7—C6	130.56 (13)	N2—C15—C8	177.71 (16)
C8—C7—H7	114.7	O1—N1—O2	123.45 (16)
C6—C7—H7	114.7	O1—N1—C2	118.39 (17)
C7—C8—C15	123.40 (13)	O2—N1—C2	118.15 (14)
C7—C8—C9	119.37 (13)	C9—N3—C10	122.71 (13)
C15—C8—C9	117.24 (12)	C9—N3—H3A	118.6
O3—C9—N3	123.55 (14)	C10—N3—H3A	118.6
O3—C9—C8	120.49 (13)	C11—O4—C14	106.99 (16)
N3—C9—C8	115.97 (12)
C6—C1—C2—C3	0.6 (3)	C15—C8—C9—N3	−5.4 (2)
C6—C1—C2—N1	−179.20 (14)	N3—C10—C11—C12	−94.5 (3)
C1—C2—C3—C4	−1.1 (3)	N3—C10—C11—O4	84.68 (19)
N1—C2—C3—C4	178.69 (15)	O4—C11—C12—C13	0.6 (3)
C2—C3—C4—C5	0.5 (3)	C10—C11—C12—C13	179.9 (2)
C3—C4—C5—C6	0.5 (3)	C11—C12—C13—C14	−0.9 (4)
C4—C5—C6—C1	−1.0 (3)	C12—C13—C14—O4	0.9 (4)
C4—C5—C6—C7	178.99 (15)	C1—C2—N1—O1	−174.37 (16)
C2—C1—C6—C5	0.5 (2)	C3—C2—N1—O1	5.9 (2)
C2—C1—C6—C7	−179.50 (14)	C1—C2—N1—O2	6.8 (2)
C5—C6—C7—C8	177.38 (16)	C3—C2—N1—O2	−172.96 (17)
C1—C6—C7—C8	−2.6 (3)	O3—C9—N3—C10	−0.3 (3)
C6—C7—C8—C15	1.2 (3)	C8—C9—N3—C10	179.74 (14)
C6—C7—C8—C9	−179.14 (15)	C11—C10—N3—C9	−88.52 (19)
C7—C8—C9—O3	−5.1 (2)	C12—C11—O4—C14	−0.1 (3)
C15—C8—C9—O3	174.61 (15)	C10—C11—O4—C14	−179.50 (16)
C7—C8—C9—N3	174.88 (14)	C13—C14—O4—C11	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2i	0.86	2.27	3.056 (2)	152
C5—H5···O3ii	0.93	2.49	3.337 (2)	151
C7—H7···O3ii	0.93	2.49	3.362 (2)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3AN2i	0.86	2.27	3.056(2)	152
C5H5O3ii	0.93	2.49	3.337(2)	151
C7H7O3ii	0.93	2.49	3.362(2)	156

Symmetry codes: (i) ; (ii) .