4-Amino-benzoic acid-4,4'-(propane-1,3-diyl)dipyridine (1/1).

In the crystal structure of the title compound, C(13)H(14)N(2)·C(7)H(7)NO(2), the 4,4'-trimethyl-ene-dipyridine (TMDP) mol-ecule displays an approximately planar structure, the maximum atomic deviation excluding H atoms being 0.118 (2) Å and the dihedral angle between the pyridine rings 4.59 (10)°. The TMDP and 4-amino-benzoic acid (ABA) mol-ecules are linked by O-H⋯N and N-H⋯N hydrogen bonding, while ABA mol-ecules are linked by O-H⋯O hydrogen bonding. C-H⋯π interactions are also observed between the methyl-ene groups of TMDP mol-ecules and the benzene rings of ABA mol-ecules.

Related literature

For general background to 4-amino­benzoic acid as a ligand, see: Smith et al. (2005 ▶). For related structures, see: Lynch & McClenaghan (2001 ▶); Smith et al. (1997 ▶, 2000 ▶).

Experimental

Crystal data

C13H14N2·C7H7NO2

M = 335.40

Monoclinic,

a = 7.6417 (6) Å

b = 11.1708 (9) Å

c = 20.8775 (18) Å

β = 99.436 (2)°

V = 1758.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 297 K

0.60 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer

9816 measured reflections

3470 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.02

3470 reflections

238 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039528/xu5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039528/xu5045Isup2.hkl

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

C13H14N2·C7H7NO2	F(000) = 712
Mr = 335.40	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2559 reflections
a = 7.6417 (6) Å	θ = 2.7–25.5°
b = 11.1708 (9) Å	µ = 0.08 mm−1
c = 20.8775 (18) Å	T = 297 K
β = 99.436 (2)°	Block, colorless
V = 1758.1 (2) Å3	0.60 × 0.20 × 0.17 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −9→9
9816 measured reflections	k = −12→13
3470 independent reflections	l = −21→25

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.1063P] where P = (Fo2 + 2Fc2)/3
3470 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.14 e Å−3
3 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.2978 (2)	0.32540 (12)	0.38052 (6)	0.0690 (4)
O2	0.3140 (2)	0.13738 (12)	0.41752 (7)	0.0628 (4)
N1	−0.0339 (3)	0.04320 (17)	0.12447 (8)	0.0627 (5)
C1	0.1876 (2)	0.24074 (15)	0.25210 (9)	0.0464 (5)
H1	0.2285	0.3192	0.2564	0.056*
C2	0.1117 (2)	0.19990 (15)	0.19194 (9)	0.0470 (5)
H2	0.1027	0.2507	0.1563	0.056*
C3	0.0479 (2)	0.08273 (15)	0.18373 (8)	0.0449 (4)
C4	0.0743 (2)	0.00735 (15)	0.23811 (9)	0.0490 (5)
H4	0.0405	−0.0726	0.2334	0.059*
C5	0.1492 (2)	0.04932 (15)	0.29817 (8)	0.0450 (4)
H5	0.1630	−0.0021	0.3337	0.054*
C6	0.2049 (2)	0.16768 (15)	0.30680 (8)	0.0422 (4)
C7	0.2759 (3)	0.21774 (17)	0.37126 (9)	0.0497 (5)
N2	0.4334 (2)	0.23425 (14)	0.53122 (8)	0.0576 (4)
N3	0.8995 (3)	0.22955 (18)	1.01679 (8)	0.0715 (5)
C8	0.4148 (3)	0.35141 (18)	0.53916 (10)	0.0701 (6)
H8	0.3645	0.3966	0.5034	0.084*
C9	0.4660 (3)	0.40938 (18)	0.59730 (9)	0.0643 (6)
H9	0.4518	0.4918	0.5999	0.077*
C10	0.5383 (2)	0.34557 (15)	0.65190 (8)	0.0433 (4)
C11	0.5601 (3)	0.22429 (16)	0.64341 (9)	0.0556 (5)
H11	0.6105	0.1771	0.6783	0.067*
C12	0.5072 (3)	0.17298 (18)	0.58325 (9)	0.0599 (6)
H12	0.5241	0.0911	0.5789	0.072*
C13	0.5864 (2)	0.40875 (15)	0.71617 (8)	0.0480 (5)
H13A	0.4796	0.4454	0.7268	0.058*
H13B	0.6680	0.4730	0.7107	0.058*
C14	0.6693 (2)	0.33409 (16)	0.77385 (8)	0.0467 (5)
H14A	0.7819	0.3024	0.7659	0.056*
H14B	0.5922	0.2670	0.7791	0.056*
C15	0.6987 (3)	0.40804 (16)	0.83572 (8)	0.0506 (5)
H15A	0.7788	0.4730	0.8299	0.061*
H15B	0.5862	0.4436	0.8410	0.061*
C16	0.7721 (2)	0.34403 (17)	0.89766 (9)	0.0482 (5)
C17	0.7995 (3)	0.22242 (19)	0.90228 (10)	0.0707 (6)
H17	0.7763	0.1750	0.8653	0.085*
C18	0.8616 (3)	0.1705 (2)	0.96176 (11)	0.0794 (7)
H18	0.8776	0.0879	0.9630	0.095*
C19	0.8731 (3)	0.3476 (2)	1.01235 (10)	0.0758 (7)
H19	0.8981	0.3926	1.0502	0.091*
C20	0.8115 (3)	0.4068 (2)	0.95554 (10)	0.0671 (6)
H20	0.7961	0.4894	0.9559	0.080*
H1A	−0.062 (3)	0.0975 (14)	0.0954 (8)	0.081 (8)*
H1B	−0.094 (2)	−0.0219 (10)	0.1227 (10)	0.078 (8)*
H2A	0.350 (3)	0.167 (2)	0.4531 (6)	0.103 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0985 (12)	0.0443 (8)	0.0564 (9)	−0.0035 (8)	−0.0104 (8)	−0.0094 (7)
O2	0.0919 (11)	0.0506 (8)	0.0408 (8)	0.0001 (7)	−0.0047 (7)	−0.0014 (7)
N1	0.0825 (14)	0.0561 (11)	0.0444 (10)	−0.0045 (11)	−0.0043 (9)	−0.0057 (10)
C1	0.0511 (11)	0.0361 (9)	0.0506 (11)	−0.0010 (8)	0.0043 (9)	−0.0006 (8)
C2	0.0559 (12)	0.0445 (10)	0.0398 (10)	0.0029 (9)	0.0052 (9)	0.0050 (8)
C3	0.0484 (11)	0.0443 (10)	0.0411 (10)	0.0031 (8)	0.0046 (8)	−0.0053 (8)
C4	0.0589 (12)	0.0366 (9)	0.0509 (11)	−0.0040 (9)	0.0068 (9)	−0.0032 (8)
C5	0.0511 (11)	0.0414 (10)	0.0418 (10)	0.0007 (8)	0.0052 (8)	0.0043 (8)
C6	0.0434 (10)	0.0399 (9)	0.0414 (10)	0.0032 (8)	0.0016 (8)	−0.0026 (8)
C7	0.0536 (12)	0.0464 (11)	0.0469 (11)	0.0037 (9)	0.0012 (9)	−0.0016 (9)
N2	0.0750 (12)	0.0542 (10)	0.0403 (9)	−0.0031 (9)	−0.0007 (8)	−0.0030 (8)
N3	0.0816 (13)	0.0886 (14)	0.0413 (10)	0.0064 (11)	0.0011 (9)	0.0041 (10)
C8	0.1005 (18)	0.0587 (13)	0.0430 (12)	0.0066 (12)	−0.0118 (11)	0.0034 (10)
C9	0.0930 (17)	0.0475 (11)	0.0469 (12)	0.0052 (11)	−0.0046 (11)	0.0028 (10)
C10	0.0459 (11)	0.0444 (10)	0.0388 (10)	−0.0034 (8)	0.0047 (8)	−0.0008 (8)
C11	0.0769 (14)	0.0484 (11)	0.0390 (11)	0.0047 (10)	0.0019 (10)	0.0027 (9)
C12	0.0829 (15)	0.0472 (11)	0.0473 (12)	−0.0006 (11)	0.0038 (11)	−0.0031 (9)
C13	0.0558 (12)	0.0454 (10)	0.0414 (10)	−0.0013 (9)	0.0042 (9)	−0.0026 (9)
C14	0.0506 (11)	0.0498 (10)	0.0390 (10)	0.0000 (9)	0.0050 (8)	−0.0014 (8)
C15	0.0573 (12)	0.0524 (11)	0.0411 (10)	−0.0008 (9)	0.0052 (9)	−0.0024 (9)
C16	0.0488 (11)	0.0576 (12)	0.0380 (10)	−0.0023 (9)	0.0062 (8)	−0.0029 (9)
C17	0.1055 (18)	0.0632 (13)	0.0407 (12)	0.0134 (13)	0.0039 (11)	−0.0054 (10)
C18	0.115 (2)	0.0710 (14)	0.0498 (14)	0.0199 (14)	0.0069 (13)	0.0050 (12)
C19	0.0960 (19)	0.0853 (17)	0.0408 (13)	−0.0093 (14)	−0.0048 (12)	−0.0106 (12)
C20	0.0840 (16)	0.0632 (13)	0.0495 (13)	−0.0069 (12)	−0.0026 (11)	−0.0086 (11)

O1—C7	1.225 (2)	C9—H9	0.9300
O2—C7	1.316 (2)	C10—C11	1.380 (2)
O2—H2A	0.819 (15)	C10—C13	1.507 (2)
N1—C3	1.365 (2)	C11—C12	1.379 (3)
N1—H1A	0.860 (16)	C11—H11	0.9300
N1—H1B	0.858 (13)	C12—H12	0.9300
C1—C2	1.372 (2)	C13—C14	1.515 (2)
C1—C6	1.392 (2)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.398 (2)	C14—C15	1.519 (2)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.401 (2)	C14—H14B	0.9700
C4—C5	1.373 (2)	C15—C16	1.503 (2)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.392 (2)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.376 (3)
C6—C7	1.476 (2)	C16—C20	1.387 (3)
N2—C12	1.329 (2)	C17—C18	1.382 (3)
N2—C8	1.330 (2)	C17—H17	0.9300
N3—C18	1.316 (3)	C18—H18	0.9300
N3—C19	1.335 (3)	C19—C20	1.373 (3)
C8—C9	1.375 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.381 (2)
C7—O2—H2A	112.9 (18)	C10—C11—H11	120.0
C3—N1—H1A	115.9 (15)	N2—C12—C11	123.50 (18)
C3—N1—H1B	118.4 (15)	N2—C12—H12	118.2
H1A—N1—H1B	120 (2)	C11—C12—H12	118.2
C2—C1—C6	121.66 (16)	C10—C13—C14	117.31 (15)
C2—C1—H1	119.2	C10—C13—H13A	108.0
C6—C1—H1	119.2	C14—C13—H13A	108.0
C1—C2—C3	120.68 (17)	C10—C13—H13B	108.0
C1—C2—H2	119.7	C14—C13—H13B	108.0
C3—C2—H2	119.7	H13A—C13—H13B	107.2
N1—C3—C2	120.86 (17)	C13—C14—C15	111.15 (15)
N1—C3—C4	121.59 (17)	C13—C14—H14A	109.4
C2—C3—C4	117.54 (16)	C15—C14—H14A	109.4
C5—C4—C3	121.20 (16)	C13—C14—H14B	109.4
C5—C4—H4	119.4	C15—C14—H14B	109.4
C3—C4—H4	119.4	H14A—C14—H14B	108.0
C4—C5—C6	121.04 (16)	C16—C15—C14	117.08 (16)
C4—C5—H5	119.5	C16—C15—H15A	108.0
C6—C5—H5	119.5	C14—C15—H15A	108.0
C5—C6—C1	117.71 (16)	C16—C15—H15B	108.0
C5—C6—C7	122.47 (16)	C14—C15—H15B	108.0
C1—C6—C7	119.81 (16)	H15A—C15—H15B	107.3
O1—C7—O2	123.08 (17)	C17—C16—C20	115.43 (19)
O1—C7—C6	122.41 (17)	C17—C16—C15	124.14 (17)
O2—C7—C6	114.51 (16)	C20—C16—C15	120.40 (18)
C12—N2—C8	116.41 (17)	C16—C17—C18	120.2 (2)
C18—N3—C19	115.21 (19)	C16—C17—H17	119.9
N2—C8—C9	123.57 (19)	C18—C17—H17	119.9
N2—C8—H8	118.2	N3—C18—C17	124.6 (2)
C9—C8—H8	118.2	N3—C18—H18	117.7
C8—C9—C10	120.21 (18)	C17—C18—H18	117.7
C8—C9—H9	119.9	N3—C19—C20	124.3 (2)
C10—C9—H9	119.9	N3—C19—H19	117.9
C11—C10—C9	116.17 (17)	C20—C19—H19	117.9
C11—C10—C13	123.86 (17)	C19—C20—C16	120.3 (2)
C9—C10—C13	119.96 (16)	C19—C20—H20	119.9
C12—C11—C10	120.10 (18)	C16—C20—H20	119.9
C12—C11—H11	120.0

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82 (2)	1.81 (2)	2.632 (2)	179 (3)
N1—H1A···N3i	0.86 (2)	2.19 (2)	3.045 (3)	172 (2)
N1—H1B···O1ii	0.86 (1)	2.30 (1)	3.151 (3)	170 (1)
C13—H13A···Cg3iii	0.97	2.87	3.6606 (17)	139
C14—H14A···Cg3iv	0.97	2.88	3.6902 (17)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82 (2)	1.81 (2)	2.632 (2)	179 (3)
N1—H1A⋯N3i	0.86 (2)	2.19 (2)	3.045 (3)	172 (2)
N1—H1B⋯O1ii	0.86 (1)	2.30 (1)	3.151 (3)	170 (1)
C13—H13A⋯Cg3iii	0.97	2.87	3.6606 (17)	139
C14—H14A⋯Cg3iv	0.97	2.88	3.6902 (17)	142

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