1,2-Di-2-pyridylethyl-ene-phenyl-succinic acid (1/1).

In the title 1:1 adduct, C(10)H(10)O(4)·C(12)H(10)N(2), the two components are linked by O-H⋯N hydrogen bonds to form a one-dimensional chain. The dihedral angle between the pyridine rings is 15.68 (8)° These chains are further inter-connected by weak inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions to generate a three-dimensional network.

Related literature

For (S)- and (R,S)-phenyl­succinic acids, see: Fischer & Profir (2003a ▶,b ▶). For weak C—H⋯O hydrogen bonds, see, for example: Bhogala et al. (2005 ▶); Wang et al. (2008 ▶). For C—H⋯π inter­actions, see, for example: Fun & Kia (2008 ▶).

Experimental

Crystal data

C10H10O4·C12H10N2

M = 376.40

Triclinic,

a = 8.6707 (13) Å

b = 10.9714 (17) Å

c = 11.2013 (17) Å

α = 80.801 (2)°

β = 69.696 (2)°

γ = 77.663 (2)°

V = 972.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 291 (2) K

0.34 × 0.33 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.957, T max = 0.975

7261 measured reflections

3605 independent reflections

2369 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.03

3605 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040245/si2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040245/si2134Isup2.hkl

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

C10H10O4·C12H10N2	Z = 2
Mr = 376.40	F(000) = 396
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6707 (13) Å	Cell parameters from 1614 reflections
b = 10.9714 (17) Å	θ = 2.5–26.0°
c = 11.2013 (17) Å	µ = 0.09 mm−1
α = 80.801 (2)°	T = 291 K
β = 69.696 (2)°	Block, colorless
γ = 77.663 (2)°	0.34 × 0.33 × 0.29 mm
V = 972.0 (3) Å3

Bruker SMART CCD area-detector diffractometer	3605 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
Tmin = 0.957, Tmax = 0.975	k = −13→13
7261 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1924P] where P = (Fo2 + 2Fc2)/3
3605 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.47679 (18)	0.96437 (13)	−0.17709 (14)	0.0637 (5)
H1	0.5453	0.9815	−0.2464	0.096*
O2	0.6712 (2)	0.79683 (17)	−0.17226 (16)	0.0896 (7)
O3	0.27415 (18)	0.75636 (14)	0.27577 (13)	0.0620 (4)
O4	0.45071 (18)	0.57475 (13)	0.26650 (13)	0.0618 (4)
H4	0.3867	0.5601	0.3387	0.093*
N1	0.2501 (2)	0.51408 (15)	0.50443 (15)	0.0485 (4)
N2	0.66326 (19)	0.01005 (14)	0.57849 (15)	0.0454 (4)
C1	0.1106 (3)	0.5966 (2)	0.5536 (2)	0.0546 (6)
H1A	0.0995	0.6764	0.5110	0.065*
C2	−0.0168 (3)	0.5695 (2)	0.6635 (2)	0.0567 (6)
H2	−0.1108	0.6295	0.6947	0.068*
C3	−0.0007 (3)	0.4507 (2)	0.7260 (2)	0.0561 (6)
H3	−0.0845	0.4289	0.7999	0.067*
C4	0.1410 (3)	0.3649 (2)	0.6774 (2)	0.0531 (5)
H4A	0.1531	0.2846	0.7187	0.064*
C5	0.2663 (2)	0.39814 (18)	0.56644 (18)	0.0434 (5)
C6	0.4216 (3)	0.31193 (19)	0.5089 (2)	0.0503 (5)
H6	0.4894	0.3386	0.4284	0.060*
C7	0.4745 (2)	0.20028 (18)	0.56004 (19)	0.0470 (5)
H7	0.4071	0.1742	0.6409	0.056*
C8	0.6279 (2)	0.11358 (18)	0.50279 (18)	0.0440 (5)
C9	0.7339 (3)	0.1334 (2)	0.3775 (2)	0.0657 (7)
H9	0.7090	0.2046	0.3256	0.079*
C10	0.8761 (3)	0.0464 (2)	0.3313 (2)	0.0720 (7)
H10	0.9480	0.0595	0.2485	0.086*
C11	0.9108 (3)	−0.0587 (2)	0.4075 (2)	0.0624 (6)
H11	1.0050	−0.1187	0.3775	0.075*
C12	0.8017 (3)	−0.07322 (19)	0.5304 (2)	0.0549 (6)
H12	0.8252	−0.1445	0.5827	0.066*
C13	0.5369 (2)	0.85814 (19)	−0.12306 (19)	0.0462 (5)
C14	0.4165 (2)	0.81888 (18)	0.00741 (18)	0.0427 (5)
H14	0.3682	0.8931	0.0550	0.051*
C15	0.2750 (2)	0.77139 (17)	−0.01329 (17)	0.0399 (5)
C16	0.1120 (2)	0.83595 (19)	0.02700 (19)	0.0488 (5)
H16	0.0881	0.9074	0.0694	0.059*
C17	−0.0154 (3)	0.7948 (2)	0.0046 (2)	0.0588 (6)
H17	−0.1236	0.8394	0.0316	0.071*
C18	0.0169 (3)	0.6883 (2)	−0.0573 (2)	0.0635 (6)
H18	−0.0688	0.6612	−0.0723	0.076*
C19	0.1789 (3)	0.6220 (2)	−0.0970 (2)	0.0603 (6)
H19	0.2018	0.5498	−0.1381	0.072*
C20	0.3064 (3)	0.66335 (19)	−0.07542 (19)	0.0497 (5)
H20	0.4145	0.6186	−0.1026	0.060*
C21	0.5086 (2)	0.7212 (2)	0.08432 (18)	0.0501 (5)
H21A	0.5541	0.6462	0.0396	0.060*
H21B	0.6013	0.7538	0.0899	0.060*
C22	0.3968 (2)	0.68718 (19)	0.21791 (18)	0.0438 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0595 (9)	0.0537 (9)	0.0538 (9)	−0.0004 (7)	−0.0032 (7)	0.0158 (7)
O2	0.0579 (10)	0.0906 (13)	0.0669 (11)	0.0189 (9)	0.0120 (9)	0.0282 (9)
O3	0.0591 (9)	0.0598 (10)	0.0442 (8)	0.0097 (8)	−0.0023 (7)	0.0005 (7)
O4	0.0653 (10)	0.0513 (9)	0.0446 (8)	0.0079 (7)	−0.0029 (7)	0.0062 (7)
N1	0.0520 (10)	0.0422 (10)	0.0428 (9)	−0.0012 (8)	−0.0126 (8)	0.0046 (8)
N2	0.0471 (9)	0.0384 (9)	0.0450 (9)	−0.0050 (7)	−0.0134 (8)	0.0056 (7)
C1	0.0621 (14)	0.0425 (12)	0.0498 (13)	0.0039 (10)	−0.0165 (11)	0.0013 (10)
C2	0.0534 (13)	0.0584 (14)	0.0490 (13)	0.0073 (11)	−0.0135 (10)	−0.0080 (11)
C3	0.0525 (13)	0.0640 (15)	0.0420 (12)	−0.0079 (11)	−0.0068 (10)	0.0006 (11)
C4	0.0551 (13)	0.0464 (12)	0.0479 (12)	−0.0053 (10)	−0.0107 (10)	0.0051 (10)
C5	0.0458 (11)	0.0419 (11)	0.0398 (11)	−0.0055 (9)	−0.0141 (9)	0.0012 (9)
C6	0.0508 (12)	0.0475 (12)	0.0425 (11)	−0.0031 (10)	−0.0098 (9)	0.0052 (9)
C7	0.0514 (12)	0.0457 (12)	0.0387 (11)	−0.0053 (9)	−0.0122 (9)	0.0011 (9)
C8	0.0495 (11)	0.0413 (11)	0.0397 (11)	−0.0062 (9)	−0.0150 (9)	−0.0005 (9)
C9	0.0788 (16)	0.0581 (15)	0.0403 (12)	0.0049 (12)	−0.0092 (11)	0.0063 (11)
C10	0.0762 (17)	0.0708 (17)	0.0427 (13)	0.0047 (13)	0.0013 (12)	−0.0010 (12)
C11	0.0553 (13)	0.0549 (14)	0.0608 (14)	0.0042 (11)	−0.0055 (11)	−0.0083 (12)
C12	0.0521 (12)	0.0431 (12)	0.0600 (14)	−0.0005 (10)	−0.0148 (11)	0.0038 (10)
C13	0.0405 (11)	0.0446 (12)	0.0451 (11)	−0.0064 (9)	−0.0083 (9)	0.0060 (9)
C14	0.0421 (10)	0.0409 (11)	0.0375 (10)	−0.0041 (8)	−0.0072 (8)	0.0005 (8)
C15	0.0393 (10)	0.0417 (11)	0.0325 (10)	−0.0047 (8)	−0.0081 (8)	0.0034 (8)
C16	0.0436 (11)	0.0463 (12)	0.0477 (12)	−0.0027 (9)	−0.0091 (9)	0.0012 (9)
C17	0.0378 (11)	0.0715 (16)	0.0586 (14)	−0.0083 (11)	−0.0134 (10)	0.0115 (12)
C18	0.0639 (15)	0.0765 (17)	0.0579 (14)	−0.0299 (13)	−0.0258 (12)	0.0094 (13)
C19	0.0706 (16)	0.0599 (14)	0.0529 (13)	−0.0190 (12)	−0.0183 (12)	−0.0052 (11)
C20	0.0473 (12)	0.0501 (13)	0.0457 (12)	−0.0033 (10)	−0.0113 (9)	−0.0025 (10)
C21	0.0409 (11)	0.0568 (13)	0.0450 (12)	−0.0067 (9)	−0.0094 (9)	0.0039 (10)
C22	0.0433 (11)	0.0477 (12)	0.0370 (10)	−0.0047 (9)	−0.0117 (9)	−0.0018 (9)

O1—C13	1.315 (2)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.365 (3)
O2—C13	1.204 (2)	C10—H10	0.9300
O3—C22	1.209 (2)	C11—C12	1.380 (3)
O4—C22	1.324 (2)	C11—H11	0.9300
O4—H4	0.8200	C12—H12	0.9300
N1—C1	1.347 (2)	C13—C14	1.531 (3)
N1—C5	1.352 (2)	C14—C15	1.529 (3)
N2—C12	1.344 (2)	C14—C21	1.532 (3)
N2—C8	1.352 (2)	C14—H14	0.9800
C1—C2	1.380 (3)	C15—C16	1.391 (3)
C1—H1A	0.9300	C15—C20	1.399 (3)
C2—C3	1.381 (3)	C16—C17	1.389 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.378 (3)	C17—C18	1.383 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.395 (3)	C18—C19	1.390 (3)
C4—H4A	0.9300	C18—H18	0.9300
C5—C6	1.474 (3)	C19—C20	1.387 (3)
C6—C7	1.326 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.465 (3)	C21—C22	1.513 (3)
C7—H7	0.9300	C21—H21A	0.9700
C8—C9	1.398 (3)	C21—H21B	0.9700
C9—C10	1.382 (3)
C13—O1—H1	109.5	N2—C12—H12	118.2
C22—O4—H4	109.5	C11—C12—H12	118.2
C1—N1—C5	118.17 (17)	O2—C13—O1	123.53 (18)
C12—N2—C8	118.53 (17)	O2—C13—C14	123.50 (18)
N1—C1—C2	123.70 (19)	O1—C13—C14	112.95 (16)
N1—C1—H1A	118.1	C15—C14—C13	108.73 (16)
C2—C1—H1A	118.1	C15—C14—C21	112.41 (16)
C1—C2—C3	118.01 (19)	C13—C14—C21	110.86 (15)
C1—C2—H2	121.0	C15—C14—H14	108.2
C3—C2—H2	121.0	C13—C14—H14	108.2
C4—C3—C2	119.24 (19)	C21—C14—H14	108.2
C4—C3—H3	120.4	C16—C15—C20	118.20 (19)
C2—C3—H3	120.4	C16—C15—C14	120.81 (18)
C3—C4—C5	120.13 (19)	C20—C15—C14	120.98 (17)
C3—C4—H4A	119.9	C17—C16—C15	120.7 (2)
C5—C4—H4A	119.9	C17—C16—H16	119.6
N1—C5—C4	120.74 (17)	C15—C16—H16	119.6
N1—C5—C6	115.87 (17)	C18—C17—C16	120.7 (2)
C4—C5—C6	123.39 (18)	C18—C17—H17	119.7
C7—C6—C5	126.66 (19)	C16—C17—H17	119.7
C7—C6—H6	116.7	C17—C18—C19	119.3 (2)
C5—C6—H6	116.7	C17—C18—H18	120.4
C6—C7—C8	126.93 (19)	C19—C18—H18	120.4
C6—C7—H7	116.5	C20—C19—C18	120.1 (2)
C8—C7—H7	116.5	C20—C19—H19	120.0
N2—C8—C9	120.45 (18)	C18—C19—H19	120.0
N2—C8—C7	116.06 (17)	C19—C20—C15	121.01 (19)
C9—C8—C7	123.49 (18)	C19—C20—H20	119.5
C10—C9—C8	119.6 (2)	C15—C20—H20	119.5
C10—C9—H9	120.2	C22—C21—C14	112.58 (16)
C8—C9—H9	120.2	C22—C21—H21A	109.1
C11—C10—C9	119.9 (2)	C14—C21—H21A	109.1
C11—C10—H10	120.0	C22—C21—H21B	109.1
C9—C10—H10	120.0	C14—C21—H21B	109.1
C10—C11—C12	118.0 (2)	H21A—C21—H21B	107.8
C10—C11—H11	121.0	O3—C22—O4	123.46 (18)
C12—C11—H11	121.0	O3—C22—C21	123.82 (18)
N2—C12—C11	123.6 (2)	O4—C22—C21	112.68 (16)
C5—N1—C1—C2	−0.1 (3)	O2—C13—C14—C15	−104.5 (2)
N1—C1—C2—C3	−0.5 (3)	O1—C13—C14—C15	74.0 (2)
C1—C2—C3—C4	0.6 (3)	O2—C13—C14—C21	19.5 (3)
C2—C3—C4—C5	0.0 (3)	O1—C13—C14—C21	−161.95 (18)
C1—N1—C5—C4	0.7 (3)	C13—C14—C15—C16	−114.07 (19)
C1—N1—C5—C6	−179.70 (18)	C21—C14—C15—C16	122.80 (19)
C3—C4—C5—N1	−0.6 (3)	C13—C14—C15—C20	64.7 (2)
C3—C4—C5—C6	179.8 (2)	C21—C14—C15—C20	−58.5 (2)
N1—C5—C6—C7	171.0 (2)	C20—C15—C16—C17	−0.8 (3)
C4—C5—C6—C7	−9.4 (3)	C14—C15—C16—C17	178.00 (17)
C5—C6—C7—C8	179.33 (19)	C15—C16—C17—C18	0.5 (3)
C12—N2—C8—C9	−0.3 (3)	C16—C17—C18—C19	0.2 (3)
C12—N2—C8—C7	179.38 (18)	C17—C18—C19—C20	−0.5 (3)
C6—C7—C8—N2	173.9 (2)	C18—C19—C20—C15	0.3 (3)
C6—C7—C8—C9	−6.4 (4)	C16—C15—C20—C19	0.4 (3)
N2—C8—C9—C10	−0.2 (3)	C14—C15—C20—C19	−178.39 (18)
C7—C8—C9—C10	−179.9 (2)	C15—C14—C21—C22	−62.5 (2)
C8—C9—C10—C11	0.9 (4)	C13—C14—C21—C22	175.58 (17)
C9—C10—C11—C12	−0.9 (4)	C14—C21—C22—O3	−26.4 (3)
C8—N2—C12—C11	0.3 (3)	C14—C21—C22—O4	155.70 (18)
C10—C11—C12—N2	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1	0.82	1.88	2.699 (2)	176
O1—H1···N2i	0.82	1.88	2.683 (2)	165
C2—H2···O2ii	0.93	2.56	3.472 (3)	164
C11—H11···O3iii	0.93	2.43	3.350 (3)	170
C3—H3···Cg1iv	0.93	2.86	3.650 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N1	0.82	1.88	2.699 (2)	176
O1—H1⋯N2i	0.82	1.88	2.683 (2)	165
C2—H2⋯O2ii	0.93	2.56	3.472 (3)	164
C11—H11⋯O3iii	0.93	2.43	3.350 (3)	170
C3—H3⋯Cg1iv	0.93	2.86	3.650 (4)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C15–C20 phenyl ring.