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

Lu, J.; Liu, X.; Li, L.; Chen, Y.; Shen, G.

doi:10.1107/S1600536811041596

organic compounds

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Volume 67| Part 11| November 2011| Page o3064

doi:10.1107/S1600536811041596

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

Ji-lin Lu,^a ^* Xue-wen Liu,^a Lin Li,^a Yuan-dao Chen ^a and Guang-yu Shen ^a

^aCollege of Chemistry and Chemical Engineering, Hunan University of Arts and Science, ChangDe, Hunan provice 415000, People's Republic of China
^*Correspondence e-mail: lu_j_l@163.com

(Received 17 September 2011; accepted 10 October 2011; online 29 October 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z-1.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041596/lh5338sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811041596/lh5338Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).

Figures top

	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.

N,N'-Bis(pyridin-3-yl)terephthalamide; terephthalic acid top

Crystal data top

C₁₈H₁₄N₄O₂·C₈H₆O₄	F(000) = 504
M_r = 484.46	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0378P)² + 0.3019P] where P = (F_o² + 2F_c²)/3
1939 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₄N₄O₂·C₈H₆O₄	V = 1102.73 (4) Å³
M_r = 484.46	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0001 (3) Å	µ = 0.11 mm⁻¹
b = 10.8080 (2) Å	T = 296 K
c = 9.6903 (2) Å	0.25 × 0.24 × 0.22 mm
β = 106.830 (2)°

Data collection top

Bruker SMART CCD diffractometer	1939 independent reflections
Absorption correction: multi-scan (SABADS; Sheldrick, 1996)	1640 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.977	R_int = 0.035
8117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.14 e Å⁻³
1939 reflections	Δρ_min = −0.19 e Å⁻³
171 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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···N1^iv	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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₄O₂·C₈H₆O₄
M_r	484.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.0001 (3), 10.8080 (2), 9.6903 (2)
β (°)	106.830 (2)
V (Å³)	1102.73 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SABADS; Sheldrick, 1996)
T_min, T_max	0.974, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	8117, 1939, 1640
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.095, 1.07
No. of reflections	1939
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) x, y+1, z−1.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S., Yang, T., Li, Z. & Yu, X. (2009). Acta Cryst. E65, o2198. Web of Science CrossRef IUCr Journals Google Scholar
Xiao, W., Xue, R. & Yin, Y. (2011). Acta Cryst. E67, o1333. Web of Science CSD CrossRef IUCr Journals Google Scholar

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