1,3-Di-4-pyrid-ylpropane-2-hydroxy-benzene-1,4-dicarboxylic acid (1/2).

In the title compound, C(13)H(14)N(2)·2C(8)H(6)O(5), which crystallized in the monoclinic C2/c space group, the 1,3-bis-(4-pyrid-yl)propane mol-ecules and 2-hydr-oxy-1,4-benzene-dicarboxylic acid mol-ecules are alternately linked by O-H⋯N and O-H⋯O hydrogen bonds into herringbone/zigzag chains.

Related literature

For general background, see: Bowers et al. (2005 ▶); Mukherjee et al. (2004 ▶). For the substitution of bromine for n class="Chemical">hydroxyl, see: Chen & Tong (2007 ▶); Zhang (2005 ▶).

Experimental

Crystal data

C13H14N2·2C8H6O5

M = 562.52

Monoclinic,

a = 22.939 (11) Å

b = 4.781 (2) Å

c = 24.163 (11) Å

β = 96.542 (6)°

V = 2633 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 291 (2) K

0.35 × 0.19 × 0.05 mm

Data collection

Bruker CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.963, T max = 0.994

9178 measured reflections

2444 independent reflections

1335 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.173

S = 1.03

2444 reflections

187 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAIn class="Chemical">NT; 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 global, I. DOI: 10.1107/S1600536808037835/ww2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037835/ww2129Isup2.hkl

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

C13H14N2·2C8H6O5	F000 = 1176
Mr = 562.52	Dx = 1.419 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1102 reflections
a = 22.939 (11) Å	θ = 3.4–23.3º
b = 4.781 (2) Å	µ = 0.11 mm−1
c = 24.163 (11) Å	T = 291 (2) K
β = 96.542 (6)º	Block, colorless
V = 2633 (2) Å3	0.35 × 0.19 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2444 independent reflections
Radiation source: fine-focus sealed tube	1335 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 291(2) K	θmax = 25.5º
ω & φ scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −27→27
Tmin = 0.963, Tmax = 0.994	k = −5→5
9178 measured reflections	l = −29→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.0772P)2 + 1.353P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2444 reflections	Δρmax = 0.39 e Å−3
187 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
O1	0.38415 (11)	1.0471 (6)	0.32590 (9)	0.0857 (9)
H1	0.3557	0.9516	0.3141	0.129*
O2	0.24082 (9)	0.8169 (5)	0.40221 (9)	0.0642 (7)
H2	0.2203	0.6976	0.3852	0.096*
O3	0.29118 (9)	0.7716 (5)	0.32941 (9)	0.0695 (7)
O4	0.43663 (9)	1.8252 (5)	0.51792 (9)	0.0666 (7)
H4	0.4624	1.9400	0.5274	0.100*
O5	0.48854 (9)	1.7794 (5)	0.44642 (10)	0.0679 (7)
N1	0.17662 (11)	0.4242 (5)	0.35544 (11)	0.0516 (7)
C1	0.32537 (12)	1.0947 (6)	0.40090 (12)	0.0467 (7)
C2	0.37382 (13)	1.1721 (6)	0.37430 (13)	0.0539 (8)
C3	0.41262 (13)	1.3722 (6)	0.39812 (13)	0.0568 (8)
H3	0.4451	1.4215	0.3805	0.068*
C4	0.40338 (12)	1.4989 (6)	0.44770 (12)	0.0470 (7)
C5	0.35515 (13)	1.4263 (6)	0.47459 (13)	0.0535 (8)
H5	0.3486	1.5125	0.5078	0.064*
C6	0.31687 (13)	1.2222 (6)	0.45088 (13)	0.0551 (8)
H6	0.2849	1.1702	0.4690	0.066*
C7	0.28337 (13)	0.8782 (6)	0.37506 (14)	0.0527 (8)
C8	0.44604 (13)	1.7142 (6)	0.47143 (13)	0.0493 (8)
C9	0.18299 (12)	0.3070 (7)	0.30666 (13)	0.0534 (8)
H9	0.2147	0.3584	0.2881	0.064*
C10	0.14366 (12)	0.1103 (6)	0.28276 (12)	0.0516 (8)
H10	0.1493	0.0298	0.2488	0.062*
C11	0.09577 (12)	0.0334 (6)	0.30954 (12)	0.0449 (7)
C12	0.09152 (13)	0.1551 (7)	0.36110 (13)	0.0570 (8)
H12	0.0609	0.1056	0.3813	0.068*
C13	0.13223 (14)	0.3479 (7)	0.38230 (13)	0.0575 (8)
H13	0.1285	0.4277	0.4168	0.069*
C14	0.04828 (11)	−0.1557 (6)	0.28235 (12)	0.0499 (8)
H14A	0.0318	−0.2651	0.3106	0.060*
H14B	0.0648	−0.2837	0.2572	0.060*
C15	0.0000	0.0194 (8)	0.2500	0.0498 (11)
H15A	0.0176	0.1391	0.2241	0.060*	0.50
H15B	−0.0176	0.1391	0.2759	0.060*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.109 (2)	0.092 (2)	0.0608 (15)	−0.0379 (16)	0.0301 (15)	−0.0327 (13)
O2	0.0605 (14)	0.0580 (14)	0.0726 (15)	−0.0154 (11)	0.0015 (12)	−0.0059 (12)
O3	0.0756 (15)	0.0679 (16)	0.0653 (15)	−0.0160 (12)	0.0091 (12)	−0.0159 (12)
O4	0.0658 (14)	0.0597 (14)	0.0748 (16)	−0.0169 (12)	0.0102 (12)	−0.0179 (13)
O5	0.0593 (14)	0.0617 (15)	0.0858 (16)	−0.0161 (12)	0.0222 (12)	−0.0191 (12)
N1	0.0513 (15)	0.0481 (15)	0.0543 (16)	−0.0003 (12)	0.0012 (13)	0.0053 (13)
C1	0.0496 (18)	0.0359 (16)	0.0527 (18)	−0.0006 (13)	−0.0027 (14)	−0.0012 (14)
C2	0.0597 (19)	0.0483 (18)	0.0543 (19)	−0.0076 (16)	0.0086 (15)	−0.0058 (16)
C3	0.059 (2)	0.0497 (19)	0.063 (2)	−0.0116 (16)	0.0148 (16)	−0.0048 (16)
C4	0.0456 (17)	0.0362 (17)	0.0578 (19)	0.0010 (13)	−0.0004 (15)	0.0018 (15)
C5	0.0593 (19)	0.0459 (18)	0.0552 (19)	−0.0024 (16)	0.0061 (15)	−0.0058 (15)
C6	0.0499 (18)	0.0527 (19)	0.063 (2)	−0.0059 (16)	0.0087 (15)	0.0009 (17)
C7	0.0475 (18)	0.0449 (18)	0.065 (2)	−0.0004 (14)	0.0028 (16)	0.0041 (17)
C8	0.0513 (18)	0.0350 (16)	0.061 (2)	0.0017 (14)	0.0033 (16)	−0.0043 (15)
C9	0.0450 (17)	0.055 (2)	0.061 (2)	−0.0051 (15)	0.0094 (15)	0.0089 (17)
C10	0.0518 (18)	0.0529 (19)	0.0509 (18)	0.0026 (15)	0.0093 (15)	0.0022 (15)
C11	0.0465 (17)	0.0364 (16)	0.0508 (17)	0.0044 (13)	0.0008 (14)	0.0045 (14)
C12	0.0504 (18)	0.064 (2)	0.059 (2)	−0.0045 (16)	0.0137 (15)	−0.0006 (17)
C13	0.062 (2)	0.058 (2)	0.0532 (19)	−0.0054 (17)	0.0070 (16)	−0.0081 (16)
C14	0.0467 (17)	0.0411 (17)	0.0607 (19)	−0.0015 (14)	0.0010 (14)	0.0004 (15)
C15	0.049 (2)	0.038 (2)	0.061 (3)	0.000	0.002 (2)	0.000

O1—C2	1.358 (3)	C5—C6	1.391 (4)
O1—H1	0.8200	C5—H5	0.9300
O2—C7	1.271 (3)	C6—H6	0.9300
O2—H2	0.8200	C9—C10	1.383 (4)
O3—C7	1.246 (4)	C9—H9	0.9300
O4—C8	1.283 (3)	C10—C11	1.387 (4)
O4—H4	0.8200	C10—H10	0.9300
O5—C8	1.244 (3)	C11—C12	1.389 (4)
N1—C13	1.320 (4)	C11—C14	1.507 (4)
N1—C9	1.328 (4)	C12—C13	1.369 (4)
C1—C6	1.386 (4)	C12—H12	0.9300
C1—C2	1.396 (4)	C13—H13	0.9300
C1—C7	1.501 (4)	C14—C15	1.530 (3)
C2—C3	1.386 (4)	C14—H14A	0.9700
C3—C4	1.380 (4)	C14—H14B	0.9700
C3—H3	0.9300	C15—C14i	1.530 (3)
C4—C5	1.389 (4)	C15—H15A	0.9700
C4—C8	1.489 (4)	C15—H15B	0.9700
C2—O1—H1	109.5	N1—C9—C10	121.7 (3)
C7—O2—H2	109.5	N1—C9—H9	119.2
C8—O4—H4	109.5	C10—C9—H9	119.2
C13—N1—C9	119.3 (3)	C9—C10—C11	120.0 (3)
C6—C1—C2	118.9 (3)	C9—C10—H10	120.0
C6—C1—C7	121.2 (3)	C11—C10—H10	120.0
C2—C1—C7	119.9 (3)	C10—C11—C12	116.6 (3)
O1—C2—C3	119.6 (3)	C10—C11—C14	121.8 (3)
O1—C2—C1	120.4 (3)	C12—C11—C14	121.4 (3)
C3—C2—C1	119.9 (3)	C13—C12—C11	120.2 (3)
C4—C3—C2	120.6 (3)	C13—C12—H12	119.9
C4—C3—H3	119.7	C11—C12—H12	119.9
C2—C3—H3	119.7	N1—C13—C12	122.3 (3)
C3—C4—C5	120.4 (3)	N1—C13—H13	118.9
C3—C4—C8	118.6 (3)	C12—C13—H13	118.9
C5—C4—C8	121.0 (3)	C11—C14—C15	109.9 (2)
C4—C5—C6	118.8 (3)	C11—C14—H14A	109.7
C4—C5—H5	120.6	C15—C14—H14A	109.7
C6—C5—H5	120.6	C11—C14—H14B	109.7
C1—C6—C5	121.5 (3)	C15—C14—H14B	109.7
C1—C6—H6	119.3	H14A—C14—H14B	108.2
C5—C6—H6	119.3	C14—C15—C14i	113.7 (3)
O3—C7—O2	124.0 (3)	C14—C15—H15A	108.8
O3—C7—C1	120.0 (3)	C14i—C15—H15A	108.8
O2—C7—C1	116.0 (3)	C14—C15—H15B	108.8
O5—C8—O4	122.8 (3)	C14i—C15—H15B	108.8
O5—C8—C4	120.2 (3)	H15A—C15—H15B	107.7
O4—C8—C4	117.0 (3)
C6—C1—C2—O1	178.6 (3)	C2—C1—C7—O2	179.2 (3)
C7—C1—C2—O1	−1.8 (4)	C3—C4—C8—O5	0.9 (4)
C6—C1—C2—C3	0.4 (4)	C5—C4—C8—O5	−179.0 (3)
C7—C1—C2—C3	180.0 (3)	C3—C4—C8—O4	−179.1 (3)
O1—C2—C3—C4	−179.1 (3)	C5—C4—C8—O4	1.0 (4)
C1—C2—C3—C4	−0.8 (5)	C13—N1—C9—C10	1.2 (4)
C2—C3—C4—C5	0.3 (5)	N1—C9—C10—C11	0.7 (4)
C2—C3—C4—C8	−179.5 (3)	C9—C10—C11—C12	−2.3 (4)
C3—C4—C5—C6	0.6 (4)	C9—C10—C11—C14	173.2 (3)
C8—C4—C5—C6	−179.5 (3)	C10—C11—C12—C13	2.2 (4)
C2—C1—C6—C5	0.6 (5)	C14—C11—C12—C13	−173.4 (3)
C7—C1—C6—C5	−179.0 (3)	C9—N1—C13—C12	−1.4 (5)
C4—C5—C6—C1	−1.1 (4)	C11—C12—C13—N1	−0.3 (5)
C6—C1—C7—O3	178.2 (3)	C10—C11—C14—C15	−90.2 (3)
C2—C1—C7—O3	−1.4 (4)	C12—C11—C14—C15	85.1 (3)
C6—C1—C7—O2	−1.3 (4)	C11—C14—C15—C14i	176.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ii	0.82	1.82	2.631 (3)	172
O2—H2···N1	0.82	1.75	2.568 (3)	174
O1—H1···O3	0.82	1.79	2.516 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.82	1.82	2.631 (3)	172
O2—H2⋯N1	0.82	1.75	2.568 (3)	174
O1—H1⋯O3	0.82	1.79	2.516 (3)	147

Symmetry code: (i) .