3,5-Bis[(pyridin-4-yl)meth-oxy]benzoic acid.

Single crystals of the title compound, C19H16N2O4, were obtained under hydro-thermal conditions by an unintended recrystallization of the employed microcrystalline starting material. The [(pyridin-4-yl)meth-oxy]benzoic acid unit is nearly planar, with a maximum deviation from the least-squares plane of 0.194 (2) Å. This plane is inclined by 35.82 (6)° to that defined by the second (pyridin-4-yl)meth-oxy group [in which the largest deviation from the least-squares plane is 0.013 (2) Å]. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds involving the acid hy-droxy group and a pyridine N atom into chains parallel to [-201].

Related literature

For compounds with metal-organic framework structures derived from the title compound, see: Xu et al. (2009 ▶).

Experimental

Crystal data

C19H16N2O4

M = 336.34

Monoclinic,

a = 11.1523 (6) Å

b = 11.2120 (6) Å

c = 13.9255 (7) Å

β = 102.827 (3)°

V = 1697.79 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.38 × 0.33 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.965, T max = 0.980

25948 measured reflections

3936 independent reflections

2980 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.04

3936 reflections

226 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049550/wm2702sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049550/wm2702Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049550/wm2702Isup3.cml

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

C19H16N2O4	F(000) = 704
Mr = 336.34	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9997 reflections
a = 11.1523 (6) Å	θ = 1.9–27.6°
b = 11.2120 (6) Å	µ = 0.09 mm−1
c = 13.9255 (7) Å	T = 296 K
β = 102.827 (3)°	Block, colourless
V = 1697.79 (15) Å3	0.38 × 0.33 × 0.21 mm
Z = 4

Bruker SMART CCD diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	2980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→14
Tmin = 0.965, Tmax = 0.980	k = −14→14
25948 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.2876P] where P = (Fo2 + 2Fc2)/3
3936 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

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
N1	0.68638 (16)	−0.22020 (13)	0.06179 (12)	0.0777 (4)
N2	−0.01294 (12)	0.70984 (13)	−0.08773 (10)	0.0647 (4)
O1	0.89003 (10)	0.51053 (12)	0.36115 (10)	0.0864 (4)
O2	0.78235 (10)	0.67629 (10)	0.32201 (9)	0.0756 (4)
H1A	0.8458	0.7098	0.3565	0.091*
O3	0.61952 (9)	0.19740 (9)	0.14886 (9)	0.0684 (3)
O4	0.38875 (8)	0.55619 (8)	0.10585 (7)	0.0537 (3)
C1	0.69258 (11)	0.49686 (12)	0.25395 (9)	0.0448 (3)
C2	0.70848 (11)	0.37573 (12)	0.23705 (10)	0.0482 (3)
H2A	0.7807	0.3368	0.2672	0.058*
C3	0.61508 (12)	0.31505 (12)	0.17484 (10)	0.0495 (3)
C4	0.50609 (12)	0.37228 (12)	0.13026 (10)	0.0491 (3)
H4A	0.4432	0.3302	0.0890	0.059*
C5	0.49235 (11)	0.49207 (12)	0.14796 (9)	0.0441 (3)
C6	0.58568 (11)	0.55589 (12)	0.21024 (9)	0.0447 (3)
H6A	0.5761	0.6366	0.2221	0.054*
C7	0.79339 (18)	−0.16440 (16)	0.08353 (15)	0.0779 (5)
H7A	0.8616	−0.2048	0.0720	0.093*
C8	0.81162 (14)	−0.05037 (14)	0.12215 (12)	0.0618 (4)
H8A	0.8892	−0.0155	0.1348	0.074*
C9	0.71223 (12)	0.00998 (12)	0.14135 (9)	0.0473 (3)
C10	0.59962 (14)	−0.04711 (14)	0.11926 (11)	0.0578 (4)
H10A	0.5298	−0.0094	0.1307	0.069*
C11	0.59181 (16)	−0.16036 (15)	0.08012 (13)	0.0687 (4)
H11A	0.5151	−0.1971	0.0657	0.082*
C12	−0.00017 (14)	0.59958 (16)	−0.11826 (12)	0.0647 (4)
H12A	−0.0621	0.5683	−0.1678	0.078*
C13	0.09988 (13)	0.52908 (15)	−0.08048 (10)	0.0558 (4)
H13A	0.1048	0.4520	−0.1040	0.067*
C14	0.19354 (11)	0.57435 (12)	−0.00677 (9)	0.0445 (3)
C15	0.18240 (13)	0.68999 (13)	0.02401 (10)	0.0511 (3)
H15A	0.2440	0.7243	0.0722	0.061*
C16	0.07743 (14)	0.75435 (14)	−0.01820 (12)	0.0612 (4)
H16A	0.0700	0.8321	0.0031	0.073*
C17	0.79843 (12)	0.56116 (13)	0.31786 (11)	0.0541 (3)
C18	0.72785 (12)	0.13267 (12)	0.18610 (11)	0.0522 (3)
H18A	0.7424	0.1273	0.2573	0.063*
H18B	0.7976	0.1723	0.1691	0.063*
C19	0.29911 (11)	0.49396 (12)	0.03536 (10)	0.0497 (3)
H19A	0.2697	0.4258	0.0664	0.060*
H19B	0.3359	0.4649	−0.0171	0.060*

	U11	U22	U33	U12	U13	U23
N1	0.0886 (11)	0.0541 (8)	0.0904 (10)	0.0016 (8)	0.0201 (9)	−0.0160 (7)
N2	0.0505 (7)	0.0672 (8)	0.0686 (8)	0.0100 (6)	−0.0036 (6)	0.0160 (7)
O1	0.0504 (6)	0.0758 (8)	0.1111 (10)	0.0056 (6)	−0.0290 (6)	−0.0171 (7)
O2	0.0566 (6)	0.0573 (7)	0.0939 (8)	−0.0075 (5)	−0.0237 (6)	−0.0146 (6)
O3	0.0498 (6)	0.0426 (5)	0.0982 (8)	0.0087 (4)	−0.0150 (5)	−0.0135 (5)
O4	0.0401 (5)	0.0459 (5)	0.0648 (6)	0.0070 (4)	−0.0104 (4)	−0.0112 (4)
C1	0.0367 (6)	0.0487 (7)	0.0453 (6)	−0.0037 (5)	0.0014 (5)	−0.0028 (5)
C2	0.0371 (6)	0.0481 (7)	0.0538 (7)	0.0041 (5)	−0.0016 (5)	0.0013 (6)
C3	0.0427 (7)	0.0416 (7)	0.0598 (8)	0.0021 (5)	0.0017 (6)	−0.0033 (6)
C4	0.0365 (6)	0.0461 (7)	0.0585 (8)	−0.0002 (5)	−0.0030 (5)	−0.0074 (6)
C5	0.0352 (6)	0.0446 (7)	0.0489 (7)	0.0030 (5)	0.0014 (5)	−0.0028 (5)
C6	0.0415 (7)	0.0406 (7)	0.0484 (7)	−0.0010 (5)	0.0022 (5)	−0.0041 (5)
C7	0.0740 (11)	0.0671 (11)	0.0956 (13)	0.0193 (9)	0.0255 (10)	−0.0133 (9)
C8	0.0506 (8)	0.0611 (9)	0.0731 (10)	0.0059 (7)	0.0121 (7)	−0.0047 (7)
C9	0.0500 (7)	0.0447 (7)	0.0442 (6)	0.0053 (6)	0.0044 (5)	0.0015 (5)
C10	0.0510 (8)	0.0553 (8)	0.0660 (9)	0.0029 (6)	0.0107 (7)	−0.0058 (7)
C11	0.0667 (10)	0.0596 (10)	0.0772 (10)	−0.0100 (8)	0.0107 (8)	−0.0104 (8)
C12	0.0496 (8)	0.0758 (11)	0.0586 (8)	0.0018 (7)	−0.0094 (6)	0.0037 (8)
C13	0.0458 (7)	0.0594 (9)	0.0556 (8)	0.0010 (6)	−0.0027 (6)	−0.0052 (6)
C14	0.0368 (6)	0.0499 (7)	0.0444 (6)	0.0030 (5)	0.0038 (5)	0.0013 (5)
C15	0.0459 (7)	0.0497 (8)	0.0533 (7)	0.0037 (6)	0.0014 (6)	0.0009 (6)
C16	0.0577 (9)	0.0513 (8)	0.0718 (9)	0.0105 (7)	0.0083 (7)	0.0068 (7)
C17	0.0425 (7)	0.0551 (8)	0.0578 (8)	−0.0030 (6)	−0.0037 (6)	−0.0074 (6)
C18	0.0453 (7)	0.0486 (7)	0.0569 (8)	0.0060 (6)	−0.0008 (6)	−0.0031 (6)
C19	0.0370 (7)	0.0485 (7)	0.0571 (7)	0.0037 (5)	−0.0036 (6)	−0.0084 (6)

N1—C7	1.322 (2)	C7—H7A	0.9300
N1—C11	1.322 (2)	C8—C9	1.375 (2)
N2—C12	1.325 (2)	C8—H8A	0.9300
N2—C16	1.330 (2)	C9—C10	1.382 (2)
O1—C17	1.2066 (17)	C9—C18	1.5043 (19)
O2—C17	1.3063 (18)	C10—C11	1.377 (2)
O2—H1A	0.8500	C10—H10A	0.9300
O3—C3	1.3716 (17)	C11—H11A	0.9300
O3—C18	1.4060 (16)	C12—C13	1.373 (2)
O4—C5	1.3765 (14)	C12—H12A	0.9300
O4—C19	1.4192 (14)	C13—C14	1.3879 (18)
C1—C6	1.3812 (17)	C13—H13A	0.9300
C1—C2	1.3964 (19)	C14—C15	1.3798 (19)
C1—C17	1.4962 (17)	C14—C19	1.4953 (17)
C2—C3	1.3776 (18)	C15—C16	1.3897 (19)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.3926 (18)	C16—H16A	0.9300
C4—C5	1.3802 (19)	C18—H18A	0.9700
C4—H4A	0.9300	C18—H18B	0.9700
C5—C6	1.3952 (17)	C19—H19A	0.9700
C6—H6A	0.9300	C19—H19B	0.9700
C7—C8	1.384 (2)
C7—N1—C11	115.73 (15)	C9—C10—H10A	120.3
C12—N2—C16	117.75 (13)	N1—C11—C10	124.16 (16)
C17—O2—H1A	110.9	N1—C11—H11A	117.9
C3—O3—C18	118.52 (10)	C10—C11—H11A	117.9
C5—O4—C19	115.70 (10)	N2—C12—C13	123.37 (14)
C6—C1—C2	121.42 (11)	N2—C12—H12A	118.3
C6—C1—C17	121.41 (12)	C13—C12—H12A	118.3
C2—C1—C17	117.12 (11)	C12—C13—C14	119.14 (14)
C3—C2—C1	118.66 (12)	C12—C13—H13A	120.4
C3—C2—H2A	120.7	C14—C13—H13A	120.4
C1—C2—H2A	120.7	C15—C14—C13	117.94 (12)
O3—C3—C2	125.05 (12)	C15—C14—C19	124.19 (12)
O3—C3—C4	113.87 (11)	C13—C14—C19	117.87 (12)
C2—C3—C4	121.07 (12)	C14—C15—C16	118.82 (13)
C5—C4—C3	119.29 (12)	C14—C15—H15A	120.6
C5—C4—H4A	120.4	C16—C15—H15A	120.6
C3—C4—H4A	120.4	N2—C16—C15	122.96 (14)
O4—C5—C4	123.23 (11)	N2—C16—H16A	118.5
O4—C5—C6	115.90 (11)	C15—C16—H16A	118.5
C4—C5—C6	120.87 (11)	O1—C17—O2	123.51 (13)
C1—C6—C5	118.69 (12)	O1—C17—C1	122.63 (14)
C1—C6—H6A	120.7	O2—C17—C1	113.86 (12)
C5—C6—H6A	120.7	O3—C18—C9	107.95 (11)
N1—C7—C8	124.98 (16)	O3—C18—H18A	110.1
N1—C7—H7A	117.5	C9—C18—H18A	110.1
C8—C7—H7A	117.5	O3—C18—H18B	110.1
C9—C8—C7	118.36 (15)	C9—C18—H18B	110.1
C9—C8—H8A	120.8	H18A—C18—H18B	108.4
C7—C8—H8A	120.8	O4—C19—C14	110.32 (11)
C8—C9—C10	117.45 (13)	O4—C19—H19A	109.6
C8—C9—C18	120.43 (13)	C14—C19—H19A	109.6
C10—C9—C18	122.12 (12)	O4—C19—H19B	109.6
C11—C10—C9	119.32 (14)	C14—C19—H19B	109.6
C11—C10—H10A	120.3	H19A—C19—H19B	108.1
C6—C1—C2—C3	0.4 (2)	C18—C9—C10—C11	−178.76 (14)
C17—C1—C2—C3	−176.99 (13)	C7—N1—C11—C10	0.0 (3)
C18—O3—C3—C2	−1.4 (2)	C9—C10—C11—N1	0.1 (3)
C18—O3—C3—C4	177.06 (13)	C16—N2—C12—C13	1.3 (3)
C1—C2—C3—O3	177.65 (14)	N2—C12—C13—C14	−0.3 (3)
C1—C2—C3—C4	−0.7 (2)	C12—C13—C14—C15	−1.1 (2)
O3—C3—C4—C5	−177.79 (13)	C12—C13—C14—C19	177.87 (14)
C2—C3—C4—C5	0.8 (2)	C13—C14—C15—C16	1.5 (2)
C19—O4—C5—C4	−5.20 (19)	C19—C14—C15—C16	−177.46 (13)
C19—O4—C5—C6	174.18 (11)	C12—N2—C16—C15	−0.9 (2)
C3—C4—C5—O4	178.92 (13)	C14—C15—C16—N2	−0.5 (2)
C3—C4—C5—C6	−0.4 (2)	C6—C1—C17—O1	175.83 (15)
C2—C1—C6—C5	−0.1 (2)	C2—C1—C17—O1	−6.8 (2)
C17—C1—C6—C5	177.20 (12)	C6—C1—C17—O2	−4.3 (2)
O4—C5—C6—C1	−179.31 (11)	C2—C1—C17—O2	173.04 (13)
C4—C5—C6—C1	0.1 (2)	C3—O3—C18—C9	−176.09 (13)
C11—N1—C7—C8	−0.7 (3)	C8—C9—C18—O3	147.29 (14)
N1—C7—C8—C9	1.1 (3)	C10—C9—C18—O3	−33.63 (18)
C7—C8—C9—C10	−0.9 (2)	C5—O4—C19—C14	−178.29 (11)
C7—C8—C9—C18	178.20 (15)	C15—C14—C19—O4	−3.97 (19)
C8—C9—C10—C11	0.3 (2)	C13—C14—C19—O4	177.08 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1A···N2i	0.85	1.83	2.6736 (16)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1A⋯N2i	0.85	1.83	2.6736 (16)	171

Symmetry code: (i) .