Crystal structure of bis-(prop-2-yn-1-yl) 5-nitro-isophthalate.

The whole mol-ecule of the title compound, C14H9NO6, is generated by twofold rotation symmetry; the twofold axis bis-ects the nitro group and the benzene ring. The nitro group is inclined to the benzene ring by 14.42 (9)°. The prop-2-yn-1-yl groups are inclined to the benzene ring by 13 (2)° and to each other by 24 (3)°; one directed above the plane of the benzene ring and the other below. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(18) ring motif. The dimers are linked by further C-H⋯O hydrogen bonds, forming sheets lying parallel to (100).

Related literature

For the biological activities of carboxyl­ates, see: Choudhary et al. (2002 ▸). For the uses and properties of nitro­aromatics, see: Lee et al. (2013 ▸); Somerville et al. (1995 ▸).

Experimental

Crystal data

C14H9NO6

M = 287.22

Orthorhombic,

a = 6.679 (5) Å

b = 11.679 (5) Å

c = 16.503 (5) Å

V = 1287.3 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.965, T max = 0.977

6369 measured reflections

1613 independent reflections

1316 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.136

S = 0.73

1523 reflections

98 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; 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 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989015009846/su5137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009846/su5137Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009846/su5137Isup3.cml

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015009846/su5137fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The unlabelled atoms are related to the labelled atoms by twofold rotation symmetry [symmetry code: (i) −x + , −y + , z].

Click here for additional data file.

a . DOI: 10.1107/S2056989015009846/su5137fig2.tif

A view along the a axis of the crystal packing of the title compound. The dashed lines indicate hydrogen bonds (see Table 1 for details).

CCDC reference: 1402145

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

C14H9NO6	F(000) = 592
Mr = 287.22	Dx = 1.482 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	θ = 2.5–28.4°
a = 6.679 (5) Å	µ = 0.12 mm−1
b = 11.679 (5) Å	T = 293 K
c = 16.503 (5) Å	Block, colourless
V = 1287.3 (12) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1613 independent reflections
Radiation source: fine-focus sealed tube	1316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scan	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.965, Tmax = 0.977	k = −15→7
6369 measured reflections	l = −12→22

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.1246P)2 + 0.5331P] where P = (Fo2 + 2Fc2)/3
S = 0.73	(Δ/σ)max < 0.001
1523 reflections	Δρmax = 0.26 e Å−3
98 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), 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.

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
C1	0.7500	0.2500	0.05352 (9)	0.0336 (4)
C2	0.90289 (17)	0.30592 (10)	0.01386 (7)	0.0351 (3)
H2	1.0033	0.3433	0.0426	0.042*
C3	0.90264 (16)	0.30486 (10)	−0.07063 (7)	0.0329 (3)
C4	0.7500	0.2500	−0.11315 (9)	0.0328 (4)
H4	0.7500	0.2500	−0.1695	0.039*
C5	1.07371 (18)	0.36348 (11)	−0.11169 (7)	0.0377 (3)
C6	1.2259 (2)	0.41344 (12)	−0.23491 (7)	0.0431 (3)
H6A	1.2527	0.4888	−0.2127	0.052*
H6B	1.3450	0.3669	−0.2284	0.052*
C7	1.17465 (19)	0.42270 (11)	−0.32014 (8)	0.0412 (3)
C8	1.1422 (2)	0.43439 (16)	−0.38961 (9)	0.0565 (4)
H8	1.1166	0.4436	−0.4446	0.068*
N1	0.7500	0.2500	0.14284 (8)	0.0377 (4)
O1	0.86053 (16)	0.31731 (9)	0.17767 (6)	0.0525 (3)
O3	1.21118 (18)	0.40639 (12)	−0.07644 (6)	0.0700 (4)
O2	1.05835 (13)	0.36103 (8)	−0.19240 (5)	0.0404 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0357 (8)	0.0445 (8)	0.0205 (8)	0.0030 (6)	0.000	0.000
C2	0.0344 (6)	0.0445 (6)	0.0263 (6)	−0.0024 (4)	−0.0023 (4)	−0.0013 (4)
C3	0.0328 (6)	0.0407 (6)	0.0254 (6)	−0.0011 (4)	0.0013 (4)	0.0007 (4)
C4	0.0355 (8)	0.0411 (8)	0.0218 (7)	−0.0010 (6)	0.000	0.000
C5	0.0378 (6)	0.0483 (7)	0.0270 (6)	−0.0062 (5)	0.0000 (5)	0.0015 (5)
C6	0.0392 (7)	0.0559 (7)	0.0342 (7)	−0.0110 (5)	0.0065 (5)	0.0047 (5)
C7	0.0401 (6)	0.0463 (6)	0.0370 (7)	−0.0021 (5)	0.0090 (5)	0.0045 (5)
C8	0.0549 (8)	0.0771 (10)	0.0376 (7)	−0.0064 (7)	0.0045 (6)	0.0094 (7)
N1	0.0369 (7)	0.0529 (8)	0.0234 (7)	0.0042 (6)	0.000	0.000
O1	0.0568 (6)	0.0728 (7)	0.0278 (5)	−0.0089 (5)	−0.0065 (4)	−0.0078 (4)
O3	0.0606 (7)	0.1147 (11)	0.0345 (5)	−0.0461 (7)	−0.0069 (5)	0.0068 (6)
O2	0.0393 (5)	0.0563 (6)	0.0256 (5)	−0.0124 (4)	0.0048 (3)	−0.0012 (3)

C1—C2i	1.3775 (15)	C5—O2	1.3363 (15)
C1—C2	1.3775 (15)	C6—C7	1.4517 (18)
C1—N1	1.474 (2)	C6—O2	1.4555 (15)
C2—C3	1.3944 (16)	C6—H6A	0.9700
C2—H2	0.9300	C6—H6B	0.9700
C3—C4	1.3937 (15)	C7—C8	1.175 (2)
C3—C5	1.4944 (17)	C8—H8	0.9300
C4—C3i	1.3937 (15)	N1—O1	1.2220 (12)
C4—H4	0.9300	N1—O1i	1.2220 (12)
C5—O3	1.1970 (17)
C2i—C1—C2	123.27 (14)	O2—C5—C3	112.55 (10)
C2i—C1—N1	118.36 (7)	C7—C6—O2	108.50 (11)
C2—C1—N1	118.36 (7)	C7—C6—H6A	110.0
C1—C2—C3	118.03 (11)	O2—C6—H6A	110.0
C1—C2—H2	121.0	C7—C6—H6B	110.0
C3—C2—H2	121.0	O2—C6—H6B	110.0
C4—C3—C2	120.56 (11)	H6A—C6—H6B	108.4
C4—C3—C5	122.79 (11)	C8—C7—C6	176.19 (14)
C2—C3—C5	116.64 (10)	C7—C8—H8	180.0
C3—C4—C3i	119.53 (14)	O1—N1—O1i	123.89 (15)
C3—C4—H4	120.2	O1—N1—C1	118.06 (7)
C3i—C4—H4	120.2	O1i—N1—C1	118.06 (7)
O3—C5—O2	123.52 (11)	C5—O2—C6	114.36 (9)
O3—C5—C3	123.92 (12)
C2i—C1—C2—C3	−0.45 (8)	C2—C3—C5—O2	−178.24 (10)
N1—C1—C2—C3	179.55 (8)	O2—C6—C7—C8	166 (2)
C1—C2—C3—C4	0.91 (15)	C2i—C1—N1—O1	−165.80 (8)
C1—C2—C3—C5	−178.32 (9)	C2—C1—N1—O1	14.20 (8)
C2—C3—C4—C3i	−0.46 (8)	C2i—C1—N1—O1i	14.20 (8)
C5—C3—C4—C3i	178.71 (12)	C2—C1—N1—O1i	−165.80 (8)
C4—C3—C5—O3	−176.32 (13)	O3—C5—O2—C6	1.09 (19)
C2—C3—C5—O3	2.9 (2)	C3—C5—O2—C6	−177.80 (10)
C4—C3—C5—O2	2.56 (15)	C7—C6—O2—C5	−170.29 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ii	0.97	2.46	3.334 (2)	150
C6—H6B···O1iii	0.97	2.57	3.313 (2)	134
C8—H8···O3iii	0.93	2.50	3.251 (2)	138

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6AO1i	0.97	2.46	3.334(2)	150
C6H6BO1ii	0.97	2.57	3.313(2)	134
C8H8O3ii	0.93	2.50	3.251(2)	138

Symmetry codes: (i) ; (ii) .