4-Amino-benzoic acid-1,2-bis-(4-pyrid-yl)ethane (2/1).

In the title compound, C(12)H(12)N(2)·2C(7)H(7)NO(2), the 4-amino-benzoic acid mol-ecules are linked by O-H⋯N hydrogen bonds to 1,2-bis-(4-pyrid-yl)ethane, forming linear hydrogen bonded chains parallel to [21]. The structure exhibits a hydrogen-bonding network involving COOH⋯N(pyrid-yl) and amine and carb-oxy-lic N-H⋯ O inter-actions. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.8622 (14) Å] are also present.

Related literature

For linear hydrogen bonding associations involving 4-amino­benzoic acid, see: Smith et al. (1997 ▶). For related structures, see: Smith et al. (2000 ▶, 2005 ▶); Lynch & McClenaghan (2001 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C12H12N2·2C7H7NO2

M = 458.51

Monoclinic,

a = 7.3556 (10) Å

b = 23.230 (3) Å

c = 7.9373 (11) Å

β = 115.579 (2)°

V = 1223.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 297 K

0.76 × 0.34 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SMART; Bruker, 2000 ▶) T min = 0.674, T max = 1.000

6871 measured reflections

2406 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.165

S = 1.03

2406 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020337/pb2029sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020337/pb2029Isup2.hkl

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

C12H12N2·2C7H7NO2	F(000) = 484
Mr = 458.51	Dx = 1.239 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2347 reflections
a = 7.3556 (10) Å	θ = 3.0–23.7°
b = 23.230 (3) Å	µ = 0.09 mm−1
c = 7.9373 (11) Å	T = 297 K
β = 115.579 (2)°	Parallelepiped, colorless
V = 1223.3 (3) Å3	0.76 × 0.34 × 0.22 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
graphite	Rint = 0.032
phi and ω scans	θmax = 26.1°, θmin = 1.8°
Absorption correction: multi-scan (SMART; Bruker, 2000)	h = −9→5
Tmin = 0.674, Tmax = 1.000	k = −27→28
6871 measured reflections	l = −9→9

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0959P)2 + 0.0431P] where P = (Fo2 + 2Fc2)/3
2406 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3
0 constraints

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N2	1.1453 (2)	0.43421 (8)	0.3904 (2)	0.0738 (7)
C8	1.0950 (3)	0.48682 (10)	0.3233 (3)	0.0783 (8)
C9	0.8987 (3)	0.50396 (11)	0.2231 (4)	0.0864 (9)
C10	0.7437 (3)	0.46541 (11)	0.1882 (3)	0.0739 (8)
C11	0.7978 (3)	0.41122 (10)	0.2571 (3)	0.0806 (8)
C12	0.9970 (3)	0.39735 (10)	0.3566 (3)	0.0826 (9)
C13	0.5251 (3)	0.48182 (15)	0.0801 (4)	0.1066 (13)
O1	0.4674 (2)	0.33090 (7)	0.4157 (2)	0.0841 (5)
O2	0.51671 (19)	0.40480 (7)	0.6066 (2)	0.0837 (6)
N1	1.3716 (3)	0.28863 (10)	1.0252 (3)	0.0824 (8)
C1	0.5750 (3)	0.35702 (8)	0.5572 (3)	0.0624 (6)
C2	0.7798 (3)	0.33843 (8)	0.6832 (2)	0.0560 (6)
C3	0.8914 (3)	0.36554 (8)	0.8520 (3)	0.0621 (6)
C4	1.0858 (3)	0.34892 (8)	0.9655 (3)	0.0649 (6)
C5	1.1749 (3)	0.30406 (8)	0.9143 (3)	0.0601 (6)
C6	1.0617 (3)	0.27578 (9)	0.7479 (3)	0.0722 (7)
C7	0.8687 (3)	0.29233 (9)	0.6355 (3)	0.0690 (7)
H8A	1.19710	0.51350	0.34500	0.0940*
H9A	0.87020	0.54150	0.17880	0.1040*
H11A	0.69910	0.38350	0.23650	0.0970*
H12A	1.02950	0.36010	0.40280	0.0990*
H13A	0.44700	0.44670	0.03900	0.1280*
H13B	0.48190	0.50100	0.16510	0.1280*
H1A	1.413 (4)	0.3021 (12)	1.142 (4)	0.108 (9)*
H1B	1.409 (3)	0.2543 (12)	0.988 (3)	0.095 (8)*
H2A	0.38730	0.41220	0.52780	0.1600*
H3A	0.83380	0.39560	0.88940	0.0750*
H4A	1.15800	0.36800	1.07780	0.0780*
H6A	1.11810	0.24500	0.71210	0.0870*
H7A	0.79550	0.27240	0.52510	0.0830*

	U11	U22	U33	U12	U13	U23
N2	0.0497 (10)	0.0777 (12)	0.0824 (12)	0.0081 (8)	0.0176 (9)	0.0039 (9)
C8	0.0490 (11)	0.0770 (14)	0.0935 (16)	−0.0026 (10)	0.0163 (11)	0.0066 (12)
C9	0.0549 (13)	0.0798 (15)	0.1084 (18)	0.0100 (10)	0.0201 (12)	0.0279 (13)
C10	0.0445 (10)	0.0941 (16)	0.0755 (13)	0.0038 (10)	0.0189 (9)	0.0124 (11)
C11	0.0565 (13)	0.0847 (15)	0.0937 (15)	−0.0058 (10)	0.0260 (12)	0.0087 (12)
C12	0.0670 (14)	0.0707 (13)	0.1014 (17)	0.0099 (11)	0.0281 (13)	0.0117 (12)
C13	0.0498 (13)	0.146 (3)	0.110 (2)	0.0138 (13)	0.0212 (13)	0.0438 (17)
O1	0.0607 (8)	0.0805 (10)	0.0741 (9)	−0.0025 (7)	−0.0058 (7)	−0.0085 (8)
O2	0.0553 (8)	0.0796 (10)	0.0888 (11)	0.0151 (7)	0.0052 (7)	−0.0106 (8)
N1	0.0556 (11)	0.0881 (14)	0.0825 (14)	0.0129 (10)	0.0100 (10)	0.0009 (11)
C1	0.0496 (10)	0.0616 (11)	0.0620 (11)	−0.0040 (8)	0.0110 (9)	0.0041 (9)
C2	0.0480 (10)	0.0548 (10)	0.0557 (10)	−0.0022 (8)	0.0134 (8)	0.0004 (8)
C3	0.0574 (11)	0.0591 (11)	0.0592 (11)	0.0088 (8)	0.0152 (9)	−0.0038 (9)
C4	0.0570 (11)	0.0638 (11)	0.0546 (10)	0.0021 (9)	0.0060 (9)	−0.0047 (9)
C5	0.0483 (10)	0.0596 (11)	0.0627 (11)	0.0042 (8)	0.0147 (9)	0.0075 (9)
C6	0.0662 (12)	0.0703 (12)	0.0705 (12)	0.0141 (10)	0.0206 (10)	−0.0085 (10)
C7	0.0628 (12)	0.0690 (12)	0.0593 (11)	0.0029 (9)	0.0114 (9)	−0.0099 (9)

O1—C1	1.220 (3)	C11—H11A	0.9300
O2—C1	1.310 (3)	C12—H12A	0.9300
O2—H2A	0.9000	C13—H13B	0.9700
N2—C12	1.320 (3)	C13—H13A	0.9700
N2—C8	1.321 (3)	C1—C2	1.468 (3)
N1—C5	1.377 (3)	C2—C7	1.390 (3)
N1—H1A	0.90 (3)	C2—C3	1.384 (3)
N1—H1B	0.93 (3)	C3—C4	1.376 (3)
C8—C9	1.373 (4)	C4—C5	1.382 (3)
C9—C10	1.381 (4)	C5—C6	1.386 (3)
C10—C13	1.509 (4)	C6—C7	1.366 (3)
C10—C11	1.362 (3)	C3—H3A	0.9300
C11—C12	1.369 (3)	C4—H4A	0.9300
C13—C13i	1.436 (4)	C6—H6A	0.9300
C8—H8A	0.9300	C7—H7A	0.9300
C9—H9A	0.9300
O1···N1ii	3.081 (3)	C12···H4Axi	3.0000
O1···N1iii	3.030 (3)	C13···H9Ai	2.7900
O2···N2iv	2.613 (2)	H1A···O1vii	2.14 (3)
O1···H1Aiii	2.14 (3)	H1A···H4A	2.3000
O1···H1Bii	2.16 (3)	H1B···H6A	2.3200
O1···H7A	2.5700	H1B···O1viii	2.16 (3)
O1···H11A	2.9200	H1B···C1viii	2.81 (3)
O1···H4Aiii	2.8000	H2A···C8iv	2.6900
O2···H3A	2.4500	H2A···C12iv	2.6200
O2···H8Av	2.7400	H2A···N2iv	1.7200
O2···H13Bvi	2.8400	H3A···O2	2.4500
N1···O1vii	3.030 (3)	H3A···C11xii	3.0600
N1···O1viii	3.081 (3)	H4A···H1A	2.3000
N2···O2ix	2.613 (2)	H4A···C12xii	3.0000
N2···C1ix	3.368 (3)	H4A···O1vii	2.8000
N1···H6Ax	2.9500	H6A···H1B	2.3200
N2···H2Aix	1.7200	H6A···N1xiii	2.9500
C1···N2iv	3.368 (3)	H6A···C4xiii	2.8700
C3···C9v	3.567 (3)	H6A···C5xiii	2.8100
C8···C9v	3.587 (4)	H7A···O1	2.5700
C9···C8v	3.587 (4)	H8A···O2v	2.7400
C9···C3v	3.567 (3)	H9A···C4v	2.8700
C1···H1Bii	2.81 (3)	H9A···C13i	2.7900
C3···H9Av	2.8600	H9A···C3v	2.8600
C4···H9Av	2.8700	H9A···H13Ai	2.2400
C4···H6Ax	2.8700	H11A···O1	2.9200
C5···H6Ax	2.8100	H11A···H13A	2.3500
C7···H12A	3.0300	H12A···C7	3.0300
C8···H2Aix	2.6900	H13A···H11A	2.3500
C9···H13Ai	2.7500	H13A···C9i	2.7500
C11···H3Axi	3.0600	H13A···H9Ai	2.2400
C12···H2Aix	2.6200	H13B···O2vi	2.8400
C1—O2—H2A	110.00	C13i—C13—H13A	108.00
C8—N2—C12	117.08 (19)	C13i—C13—H13B	108.00
C5—N1—H1A	111 (2)	O2—C1—C2	114.69 (17)
C5—N1—H1B	113.1 (14)	O1—C1—O2	122.1 (2)
H1A—N1—H1B	128 (2)	O1—C1—C2	123.22 (19)
N2—C8—C9	122.9 (2)	C1—C2—C7	120.41 (16)
C8—C9—C10	119.9 (2)	C3—C2—C7	117.52 (19)
C9—C10—C11	116.5 (2)	C1—C2—C3	122.07 (19)
C11—C10—C13	121.1 (2)	C2—C3—C4	121.4 (2)
C9—C10—C13	122.4 (2)	C3—C4—C5	120.6 (2)
C10—C11—C12	120.2 (2)	N1—C5—C4	120.6 (2)
N2—C12—C11	123.3 (2)	C4—C5—C6	118.1 (2)
C10—C13—C13i	117.1 (2)	N1—C5—C6	121.3 (2)
C9—C8—H8A	118.00	C5—C6—C7	121.1 (2)
N2—C8—H8A	119.00	C2—C7—C6	121.17 (19)
C8—C9—H9A	120.00	C2—C3—H3A	119.00
C10—C9—H9A	120.00	C4—C3—H3A	119.00
C10—C11—H11A	120.00	C3—C4—H4A	120.00
C12—C11—H11A	120.00	C5—C4—H4A	120.00
N2—C12—H12A	118.00	C5—C6—H6A	119.00
C11—C12—H12A	118.00	C7—C6—H6A	119.00
C10—C13—H13B	108.00	C2—C7—H7A	119.00
H13A—C13—H13B	107.00	C6—C7—H7A	119.00
C10—C13—H13A	108.00
C12—N2—C8—C9	0.3 (3)	O2—C1—C2—C3	7.6 (3)
C8—N2—C12—C11	0.0 (3)	O2—C1—C2—C7	−172.38 (19)
N2—C8—C9—C10	−0.2 (4)	C1—C2—C3—C4	−177.7 (2)
C8—C9—C10—C11	−0.3 (4)	C7—C2—C3—C4	2.3 (3)
C8—C9—C10—C13	179.6 (2)	C1—C2—C7—C6	177.6 (2)
C9—C10—C11—C12	0.6 (3)	C3—C2—C7—C6	−2.3 (3)
C13—C10—C11—C12	−179.3 (2)	C2—C3—C4—C5	−0.5 (3)
C9—C10—C13—C13i	40.3 (4)	C3—C4—C5—N1	178.0 (2)
C11—C10—C13—C13i	−139.9 (3)	C3—C4—C5—C6	−1.2 (3)
C10—C11—C12—N2	−0.4 (3)	N1—C5—C6—C7	−178.0 (2)
C10—C13—C13i—C10i	−180.0 (2)	C4—C5—C6—C7	1.2 (3)
O1—C1—C2—C3	−173.5 (2)	C5—C6—C7—C2	0.6 (3)
O1—C1—C2—C7	6.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1vii	0.90 (3)	2.14 (3)	3.030 (3)	171 (3)
N1—H1B···O1viii	0.93 (3)	2.16 (3)	3.081 (3)	172 (2)
O2—H2A···N2iv	0.90	1.72	2.613 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.90 (3)	2.14 (3)	3.030 (3)	171 (3)
N1—H1B⋯O1ii	0.93 (3)	2.16 (3)	3.081 (3)	172 (2)
O2—H2A⋯N2iii	0.90	1.72	2.613 (2)	173

Symmetry codes: (i) ; (ii) ; (iii) .