N,N′-Bis(pyridin-3-yl)terephthalamide–terephthalic acid (1/1)

Abstract

In the title compound, C₁₈H₁₄N₄O₂·C₈H₆O₄, both types of mol­ecule lie on inversion centers. In the N,N′-bis­(pyridin-3-yl)terephthalamide mol­ecule, the pyridine ring forms a dihedral angle of 11.33 (9)° with the central benzene ring. In the crystal, N—H⋯O and O—H⋯N hydrogen bonds connect the components into a three-dimensional network.

Related literature

For related structures, see: Xiao et al. (2011 ▶), Wang et al. (2009 ▶).

Experimental

Crystal data

• C₁₈H₁₄N₄O₂·C₈H₆O₄

• M _r = 484.46

• Monoclinic,

• a = 11.0001 (3) Å

• b = 10.8080 (2) Å

• c = 9.6903 (2) Å

• β = 106.830 (2)°

• V = 1102.73 (4) ų

• Z = 2

• Mo Kα radiation

• μ = 0.11 mm⁻¹

• T = 296 K

• 0.25 × 0.24 × 0.22 mm

Data collection

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SABADS; Sheldrick, 1996) ▶ T _min = 0.974, T _max = 0.977

• 8117 measured reflections

• 1939 independent reflections

• 1640 reflections with I > 2σ(I)

• R _int = 0.035

Refinement

• R[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 0.095

• S = 1.07

• 1939 reflections

• 171 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.14 e Å⁻³

• Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811041596/lh5338Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.89 (2)	1.98 (2)	2.8616 (18)	171.3 (18)
O2—H1N⋯N1ii	1.00 (3)	1.69 (3)	2.6938 (19)	178 (2)

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

Pyridine amide derivatives and carboxylic acids easily form hydrogen bonds therefore they are useful to construct supramoleculur structures (e.g. Xiao et al., 2011; Wang et al., 2009). Herein, we use N,N'-di(pyridin-3-yl)terephthalamide and terephthalic acid to construct a supramolecular compound. The crystal structure of the title compound is presented herein.

The molecular structure of the title compound is shown in Fig. 1. The symmetry unique pyridine ring forms a dihedral angle of 11.33 (9)° with the central benzene ring. In the crystal, N—H···O and O—H···N hydrogen bonds connect the components of the structure into a three dimensional network (Fig. 2).

Experimental

N,N'-di(pyridin-3-yl)terephthalamide (0.2 mmol) and terephthalic acid (0.2 mmol) was sealed in a teflon reactor with 6 mL water, and heated at 433 K for 2 days, and then cooled to room temperature. The single crystals were obtained by slow evaporation.

Refinement

H atoms bonded to C atoms were placed in calculated positions with C—H = 0.93Å and included using a riding-model approximation with U_iso(H) = 1.2U_eq(C). H atoms bonded to O and N atoms were refined independently with isotropic displacement parameters.

Figures

Fig. 1.

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level (symmetry code; (A) -x + 1, -y + 1, -z + 1; (B) -x + 2, -y + 2, -z + 1). Hydrogen atoms bonded to C atoms are not shown.

Fig. 2.

Part of the crystal structure with hydrogen bonds shown as pink dashed lines. H atoms are purple.

Crystal data

C18H14N4O2·C8H6O4	F(000) = 504
Mr = 484.46	Dx = 1.459 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2279 reflections
a = 11.0001 (3) Å	θ = 2.7–25.2°
b = 10.8080 (2) Å	µ = 0.11 mm−1
c = 9.6903 (2) Å	T = 296 K
β = 106.830 (2)°	Block, colourless
V = 1102.73 (4) Å3	0.25 × 0.24 × 0.22 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	1939 independent reflections
Radiation source: fine-focus sealed tube	1640 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SABADS; Sheldrick, 1996)	h = −13→12
Tmin = 0.974, Tmax = 0.977	k = −12→11
8117 measured reflections	l = −11→11

Refinement

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.3019P] where P = (Fo2 + 2Fc2)/3
1939 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C10	0.91350 (16)	1.01651 (17)	0.18960 (19)	0.0385 (4)
C11	0.95943 (16)	1.00643 (16)	0.35009 (18)	0.0358 (4)
C8	0.58897 (16)	0.45790 (15)	0.62372 (17)	0.0336 (4)
H8	0.6489	0.4302	0.7068	0.040*
C7	0.54563 (16)	0.37897 (14)	0.50665 (16)	0.0308 (4)
C5	0.74809 (16)	0.04149 (16)	0.79727 (18)	0.0367 (4)
H5	0.7580	0.1028	0.8671	0.044*
C3	0.66694 (17)	−0.02113 (16)	0.55212 (18)	0.0381 (4)
H3	0.6219	−0.0058	0.4565	0.046*
C6	0.59441 (16)	0.25022 (15)	0.50444 (17)	0.0339 (4)
C9	0.45681 (17)	0.42247 (15)	0.38296 (17)	0.0351 (4)
H9	0.4279	0.3704	0.3038	0.042*
C12	1.01793 (16)	0.89971 (16)	0.41856 (19)	0.0388 (4)
H12	1.0304	0.8326	0.3642	0.047*
C4	0.68076 (15)	0.06989 (15)	0.65646 (17)	0.0313 (4)
C13	0.94247 (17)	1.10642 (16)	0.43264 (19)	0.0399 (4)
H13	0.9041	1.1782	0.3874	0.048*
C2	0.72163 (18)	−0.13483 (16)	0.5939 (2)	0.0429 (5)
H2	0.7154	−0.1971	0.5259	0.051*
C1	0.78552 (18)	−0.15624 (17)	0.7362 (2)	0.0460 (5)
H1	0.8204	−0.2341	0.7630	0.055*
N1	0.79926 (14)	−0.06916 (14)	0.83764 (15)	0.0423 (4)
N2	0.62725 (14)	0.18931 (13)	0.63090 (14)	0.0338 (3)
H2N	0.6221 (18)	0.2299 (18)	0.709 (2)	0.048 (5)*
O1	0.60228 (13)	0.20383 (11)	0.39151 (12)	0.0476 (4)
O2	0.91449 (14)	0.91030 (12)	0.12264 (15)	0.0524 (4)
H1N	0.874 (3)	0.918 (3)	0.016 (3)	0.095 (9)*
O3	0.87627 (13)	1.11288 (12)	0.12828 (13)	0.0501 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C10	0.0381 (9)	0.0349 (10)	0.0398 (10)	−0.0038 (8)	0.0069 (8)	0.0027 (8)
C11	0.0364 (9)	0.0332 (10)	0.0353 (9)	−0.0037 (7)	0.0063 (7)	0.0034 (7)
C8	0.0435 (9)	0.0310 (9)	0.0255 (8)	0.0035 (7)	0.0086 (7)	0.0045 (7)
C7	0.0437 (9)	0.0256 (9)	0.0255 (8)	0.0017 (7)	0.0136 (7)	0.0033 (7)
C5	0.0458 (10)	0.0313 (10)	0.0321 (9)	0.0041 (8)	0.0100 (8)	0.0008 (7)
C3	0.0485 (10)	0.0328 (10)	0.0317 (9)	0.0024 (8)	0.0094 (8)	−0.0004 (7)
C6	0.0472 (10)	0.0294 (9)	0.0273 (9)	0.0014 (7)	0.0143 (7)	0.0014 (7)
C9	0.0514 (10)	0.0279 (9)	0.0258 (8)	0.0002 (7)	0.0109 (8)	−0.0011 (7)
C12	0.0434 (10)	0.0313 (9)	0.0388 (10)	−0.0002 (8)	0.0072 (8)	−0.0022 (8)
C4	0.0384 (9)	0.0259 (9)	0.0311 (9)	0.0028 (7)	0.0123 (7)	0.0026 (7)
C13	0.0430 (10)	0.0312 (10)	0.0408 (10)	0.0023 (8)	0.0047 (8)	0.0036 (8)
C2	0.0539 (11)	0.0282 (10)	0.0452 (11)	0.0045 (8)	0.0122 (9)	−0.0059 (8)
C1	0.0530 (11)	0.0311 (10)	0.0509 (12)	0.0092 (8)	0.0105 (9)	0.0034 (9)
N1	0.0493 (9)	0.0362 (9)	0.0377 (8)	0.0086 (7)	0.0066 (7)	0.0049 (7)
N2	0.0533 (9)	0.0253 (8)	0.0241 (7)	0.0066 (6)	0.0132 (6)	0.0012 (6)
O1	0.0845 (10)	0.0333 (7)	0.0306 (7)	0.0124 (6)	0.0255 (6)	0.0033 (5)
O2	0.0773 (10)	0.0365 (8)	0.0357 (8)	0.0039 (7)	0.0044 (7)	0.0003 (6)
O3	0.0656 (9)	0.0373 (8)	0.0401 (7)	0.0025 (6)	0.0037 (6)	0.0063 (6)

Geometric parameters (Å, °)

C10—O3	1.210 (2)	C6—O1	1.2293 (19)
C10—O2	1.320 (2)	C6—N2	1.345 (2)
C10—C11	1.494 (2)	C9—C8i	1.382 (2)
C11—C13	1.389 (2)	C9—H9	0.9300
C11—C12	1.392 (2)	C12—C13ii	1.382 (2)
C8—C9i	1.382 (2)	C12—H12	0.9300
C8—C7	1.389 (2)	C4—N2	1.410 (2)
C8—H8	0.9300	C13—C12ii	1.382 (2)
C7—C9	1.391 (2)	C13—H13	0.9300
C7—C6	1.494 (2)	C2—C1	1.374 (3)
C5—N1	1.331 (2)	C2—H2	0.9300
C5—C4	1.385 (2)	C1—N1	1.337 (2)
C5—H5	0.9300	C1—H1	0.9300
C3—C2	1.377 (2)	N2—H2N	0.89 (2)
C3—C4	1.387 (2)	O2—H1N	1.00 (3)
C3—H3	0.9300
O3—C10—O2	123.83 (16)	C8i—C9—H9	119.6
O3—C10—C11	122.57 (16)	C7—C9—H9	119.6
O2—C10—C11	113.58 (15)	C13ii—C12—C11	119.97 (16)
C13—C11—C12	119.40 (16)	C13ii—C12—H12	120.0
C13—C11—C10	118.80 (15)	C11—C12—H12	120.0
C12—C11—C10	121.80 (16)	C5—C4—C3	118.38 (15)
C9i—C8—C7	120.14 (15)	C5—C4—N2	116.91 (15)
C9i—C8—H8	119.9	C3—C4—N2	124.68 (15)
C7—C8—H8	119.9	C12ii—C13—C11	120.63 (16)
C8—C7—C9	119.05 (15)	C12ii—C13—H13	119.7
C8—C7—C6	122.97 (14)	C11—C13—H13	119.7
C9—C7—C6	117.92 (14)	C1—C2—C3	119.90 (17)
N1—C5—C4	123.26 (16)	C1—C2—H2	120.1
N1—C5—H5	118.4	C3—C2—H2	120.1
C4—C5—H5	118.4	N1—C1—C2	122.36 (17)
C2—C3—C4	118.19 (16)	N1—C1—H1	118.8
C2—C3—H3	120.9	C2—C1—H1	118.8
C4—C3—H3	120.9	C5—N1—C1	117.91 (15)
O1—C6—N2	122.81 (16)	C6—N2—C4	126.60 (14)
O1—C6—C7	120.72 (14)	C6—N2—H2N	117.7 (12)
N2—C6—C7	116.47 (14)	C4—N2—H2N	115.4 (12)
C8i—C9—C7	120.81 (15)	C10—O2—H1N	111.7 (16)
O3—C10—C11—C13	9.3 (3)	N1—C5—C4—C3	−0.6 (3)
O2—C10—C11—C13	−169.05 (16)	N1—C5—C4—N2	177.29 (16)
O3—C10—C11—C12	−171.05 (17)	C2—C3—C4—C5	−0.4 (2)
O2—C10—C11—C12	10.6 (2)	C2—C3—C4—N2	−178.11 (16)
C9i—C8—C7—C9	0.6 (3)	C12—C11—C13—C12ii	−0.6 (3)
C9i—C8—C7—C6	177.70 (15)	C10—C11—C13—C12ii	179.14 (16)
C8—C7—C6—O1	−146.83 (17)	C4—C3—C2—C1	1.3 (3)
C9—C7—C6—O1	30.4 (2)	C3—C2—C1—N1	−1.3 (3)
C8—C7—C6—N2	33.8 (2)	C4—C5—N1—C1	0.6 (3)
C9—C7—C6—N2	−149.04 (16)	C2—C1—N1—C5	0.3 (3)
C8—C7—C9—C8i	−0.6 (3)	O1—C6—N2—C4	3.8 (3)
C6—C7—C9—C8i	−177.85 (15)	C7—C6—N2—C4	−176.86 (15)
C13—C11—C12—C13ii	0.6 (3)	C5—C4—N2—C6	157.60 (17)
C10—C11—C12—C13ii	−179.13 (16)	C3—C4—N2—C6	−24.7 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1iii	0.89 (2)	1.98 (2)	2.8616 (18)	171.3 (18)
O2—H1N···N1iv	1.00 (3)	1.69 (3)	2.6938 (19)	178 (2)

Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) x, y+1, z−1.