N,N'-Bis(pyridin-3-yl)terephthalamide-terephthalic acid (1/1).

In the title compound, C(18)H(14)N(4)O(2)·C(8)H(6)O(4), both types of mol-ecule lie on inversion centers. In the N,N'-bis-(pyridin-3-yl)terephthalamide mol-ecule, 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 = 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) Å3

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

Δρmax = 0.14 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041596/lh5338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041596/lh5338Isup2.hkl

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

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

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

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 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

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
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)

	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)

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)

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)

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) .