Bis{2,6-bis-[(2-hy-droxy-5-methyl-phen-yl)imino-meth-yl]pyridine} monohydrate.

The title compound, 2C(21)H(19)N(3)O(2)·H(2)O, was synthesized by a Schiff base condensation of 2,6-diformyl-pyridine with 2-amino-4-methyl-phenol in ethanol. In the crystal, two mol-ecules of 2,6-bis-[(2-hy-droxy-5-methyl-phen-yl)imino-meth-yl]pyridine dimer-ize via hydrogen bonding to a water mol-ecule, which lies on a twofold axis. There are also intra-molecular phenol-imine hydrogen bonds. The dimers are further linked via π-π (phen-yl-pyridine) [centroid-centroid distance = 3.707 (2) Å] and π-π edge-to-edge [3.392 (2) Å] inter-actions. The dihedral angles between the central ring and the two pendant rings are 11.46 (8) and 2.06 (8)° while the pendant rings make a dihedral angle of 10.14 (8)°.

Related literature

For related structures, see: Gonzalez et al. (2008 ▶); Sun et al. (2006 ▶).

Experimental

Crystal data

2C21H19N3O2·H2O

M = 708.80

Monoclinic,

a = 23.8510 (13) Å

b = 12.9688 (7) Å

c = 12.3835 (7) Å

β = 114.077 (1)°

V = 3497.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.60 × 0.28 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.947, T max = 0.991

19364 measured reflections

5005 independent reflections

3919 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.06

5005 reflections

251 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811045399/aa2032sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045399/aa2032Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045399/aa2032Isup3.cml

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

2C21H19N3O2·H2O	F(000) = 1496
Mr = 708.80	Dx = 1.346 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5957 reflections
a = 23.8510 (13) Å	θ = 2.3–29.8°
b = 12.9688 (7) Å	µ = 0.09 mm−1
c = 12.3835 (7) Å	T = 150 K
β = 114.077 (1)°	Block, yellow
V = 3497.2 (3) Å3	0.60 × 0.28 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	5005 independent reflections
Radiation source: fine-focus sealed tube	3919 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 29.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −33→33
Tmin = 0.947, Tmax = 0.991	k = −17→18
19364 measured reflections	l = −17→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0642P)2 + 1.5272P] where P = (Fo2 + 2Fc2)/3
5005 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	0.33231 (5)	0.57957 (7)	0.14787 (9)	0.0363 (2)
H1A	0.3535 (9)	0.5552 (15)	0.1120 (17)	0.054*
C1	0.32840 (6)	0.50007 (9)	0.21682 (10)	0.0263 (2)
C2	0.29313 (6)	0.51152 (9)	0.28174 (11)	0.0295 (3)
H2	0.2724	0.5747	0.2792	0.035*
C3	0.28826 (5)	0.43063 (9)	0.35006 (11)	0.0285 (2)
H3	0.2641	0.4391	0.3944	0.034*
C4	0.31806 (5)	0.33642 (9)	0.35549 (10)	0.0259 (2)
C5	0.30934 (6)	0.24734 (10)	0.42542 (12)	0.0344 (3)
H5A	0.3220	0.1832	0.4000	0.052*
H5B	0.2660	0.2426	0.4119	0.052*
H5C	0.3344	0.2584	0.5098	0.052*
C6	0.35360 (5)	0.32612 (9)	0.29095 (10)	0.0243 (2)
H6	0.3744	0.2630	0.2942	0.029*
C7	0.35935 (5)	0.40707 (9)	0.22099 (9)	0.0232 (2)
N1	0.39157 (5)	0.40486 (7)	0.14721 (8)	0.0250 (2)
C8	0.42258 (5)	0.32597 (9)	0.14243 (9)	0.0231 (2)
H8	0.4261	0.2691	0.1931	0.028*
C9	0.45300 (5)	0.32110 (8)	0.06030 (9)	0.0209 (2)
C10	0.44553 (5)	0.39831 (9)	−0.02331 (10)	0.0250 (2)
H10	0.4218	0.4580	−0.0268	0.030*
C11	0.47345 (6)	0.38588 (9)	−0.10081 (10)	0.0274 (2)
H11	0.4695	0.4372	−0.1582	0.033*
C12	0.50726 (5)	0.29722 (9)	−0.09334 (10)	0.0251 (2)
H12	0.5265	0.2866	−0.1461	0.030*
C13	0.51268 (5)	0.22380 (8)	−0.00723 (9)	0.0205 (2)
N2	0.48638 (4)	0.23536 (7)	0.06979 (8)	0.02020 (19)
C14	0.54842 (5)	0.12966 (8)	−0.00076 (9)	0.0219 (2)
H14	0.5582	0.1125	−0.0657	0.026*
N3	0.56667 (4)	0.07051 (7)	0.08909 (8)	0.02191 (19)
C15	0.60324 (5)	−0.01660 (8)	0.09325 (9)	0.0199 (2)
C16	0.63466 (5)	−0.03133 (8)	0.02040 (9)	0.0210 (2)
H16	0.6319	0.0200	−0.0362	0.025*
C17	0.66968 (5)	−0.11873 (8)	0.02855 (9)	0.0218 (2)
C18	0.70282 (5)	−0.13137 (9)	−0.05144 (10)	0.0276 (2)
H18A	0.6833	−0.0877	−0.1215	0.041*
H18B	0.7008	−0.2036	−0.0758	0.041*
H18C	0.7459	−0.1109	−0.0090	0.041*
C19	0.67339 (5)	−0.19289 (8)	0.11334 (10)	0.0242 (2)
H19	0.6969	−0.2536	0.1200	0.029*
C20	0.64359 (5)	−0.17978 (9)	0.18780 (10)	0.0240 (2)
H20	0.6471	−0.2309	0.2452	0.029*
C21	0.60848 (5)	−0.09168 (8)	0.17862 (9)	0.0212 (2)
O2	0.57884 (4)	−0.08313 (7)	0.25167 (7)	0.02766 (19)
H2A	0.5591 (7)	−0.0281 (13)	0.2415 (13)	0.033*
O3	0.5000	0.07316 (9)	0.2500	0.0278 (3)
H3D	0.4959 (8)	0.1100 (13)	0.1942 (14)	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0520 (6)	0.0268 (4)	0.0359 (5)	0.0110 (4)	0.0239 (4)	0.0038 (4)
C1	0.0301 (6)	0.0243 (5)	0.0224 (5)	0.0038 (4)	0.0088 (4)	−0.0028 (4)
C2	0.0304 (6)	0.0275 (6)	0.0300 (6)	0.0074 (5)	0.0119 (5)	−0.0056 (5)
C3	0.0263 (5)	0.0334 (6)	0.0272 (6)	0.0027 (5)	0.0122 (5)	−0.0071 (5)
C4	0.0242 (5)	0.0290 (6)	0.0251 (5)	0.0010 (4)	0.0106 (4)	−0.0033 (4)
C5	0.0364 (7)	0.0364 (7)	0.0386 (7)	0.0026 (5)	0.0236 (6)	0.0021 (5)
C6	0.0242 (5)	0.0247 (5)	0.0241 (5)	0.0043 (4)	0.0099 (4)	−0.0023 (4)
C7	0.0237 (5)	0.0249 (5)	0.0205 (5)	0.0026 (4)	0.0084 (4)	−0.0036 (4)
N1	0.0278 (5)	0.0258 (5)	0.0226 (5)	0.0032 (4)	0.0115 (4)	−0.0022 (4)
C8	0.0235 (5)	0.0252 (5)	0.0210 (5)	0.0021 (4)	0.0097 (4)	−0.0007 (4)
C9	0.0203 (5)	0.0229 (5)	0.0193 (5)	0.0002 (4)	0.0077 (4)	−0.0021 (4)
C10	0.0268 (5)	0.0223 (5)	0.0249 (5)	0.0021 (4)	0.0098 (4)	0.0009 (4)
C11	0.0315 (6)	0.0270 (5)	0.0241 (5)	0.0007 (4)	0.0117 (5)	0.0056 (4)
C12	0.0270 (5)	0.0302 (6)	0.0199 (5)	0.0012 (4)	0.0115 (4)	0.0021 (4)
C13	0.0207 (5)	0.0242 (5)	0.0168 (4)	0.0003 (4)	0.0079 (4)	−0.0007 (4)
N2	0.0205 (4)	0.0226 (4)	0.0182 (4)	0.0003 (3)	0.0086 (3)	−0.0012 (3)
C14	0.0232 (5)	0.0267 (5)	0.0185 (5)	0.0021 (4)	0.0110 (4)	−0.0009 (4)
N3	0.0248 (4)	0.0221 (4)	0.0224 (4)	0.0006 (3)	0.0133 (4)	−0.0004 (3)
C15	0.0224 (5)	0.0201 (5)	0.0182 (5)	0.0001 (4)	0.0093 (4)	−0.0011 (4)
C16	0.0231 (5)	0.0215 (5)	0.0203 (5)	0.0003 (4)	0.0109 (4)	0.0008 (4)
C17	0.0217 (5)	0.0225 (5)	0.0223 (5)	−0.0011 (4)	0.0102 (4)	−0.0031 (4)
C18	0.0295 (6)	0.0278 (6)	0.0307 (6)	0.0032 (5)	0.0176 (5)	−0.0011 (4)
C19	0.0235 (5)	0.0218 (5)	0.0268 (5)	0.0022 (4)	0.0097 (4)	0.0000 (4)
C20	0.0263 (5)	0.0232 (5)	0.0215 (5)	−0.0003 (4)	0.0086 (4)	0.0034 (4)
C21	0.0230 (5)	0.0246 (5)	0.0171 (5)	−0.0023 (4)	0.0093 (4)	−0.0008 (4)
O2	0.0370 (5)	0.0287 (4)	0.0239 (4)	0.0042 (4)	0.0191 (4)	0.0038 (3)
O3	0.0386 (7)	0.0270 (6)	0.0266 (6)	0.000	0.0223 (5)	0.000

O1—C1	1.3660 (15)	C11—H11	0.9500
O1—H1A	0.86 (2)	C12—C13	1.3957 (15)
C1—C2	1.3884 (16)	C12—H12	0.9500
C1—C7	1.4040 (15)	C13—N2	1.3467 (13)
C2—C3	1.3821 (18)	C13—C14	1.4725 (15)
C2—H2	0.9500	C14—N3	1.2731 (14)
C3—C4	1.4012 (16)	C14—H14	0.9500
C3—H3	0.9500	N3—C15	1.4153 (13)
C4—C6	1.3885 (15)	C15—C16	1.4013 (14)
C4—C5	1.5083 (17)	C15—C21	1.4048 (14)
C5—H5A	0.9800	C16—C17	1.3870 (15)
C5—H5B	0.9800	C16—H16	0.9500
C5—H5C	0.9800	C17—C19	1.3998 (15)
C6—C7	1.4030 (16)	C17—C18	1.5072 (15)
C6—H6	0.9500	C18—H18A	0.9800
C7—N1	1.4139 (14)	C18—H18B	0.9800
N1—C8	1.2778 (14)	C18—H18C	0.9800
C8—C9	1.4721 (15)	C19—C20	1.3853 (15)
C8—H8	0.9500	C19—H19	0.9500
C9—N2	1.3445 (14)	C20—C21	1.3934 (15)
C9—C10	1.3985 (15)	C20—H20	0.9500
C10—C11	1.3827 (16)	C21—O2	1.3610 (13)
C10—H10	0.9500	O2—H2A	0.836 (17)
C11—C12	1.3857 (16)	O3—H3D	0.812 (16)
C1—O1—H1A	104.5 (13)	C12—C11—H11	120.6
O1—C1—C2	119.56 (10)	C11—C12—C13	119.14 (10)
O1—C1—C7	120.15 (10)	C11—C12—H12	120.4
C2—C1—C7	120.28 (11)	C13—C12—H12	120.4
C3—C2—C1	119.70 (10)	N2—C13—C12	122.72 (10)
C3—C2—H2	120.2	N2—C13—C14	118.71 (9)
C1—C2—H2	120.2	C12—C13—C14	118.57 (9)
C2—C3—C4	121.56 (11)	C9—N2—C13	117.41 (9)
C2—C3—H3	119.2	N3—C14—C13	122.07 (9)
C4—C3—H3	119.2	N3—C14—H14	119.0
C6—C4—C3	118.25 (11)	C13—C14—H14	119.0
C6—C4—C5	121.09 (10)	C14—N3—C15	119.91 (9)
C3—C4—C5	120.61 (10)	C16—C15—C21	118.89 (9)
C4—C5—H5A	109.5	C16—C15—N3	124.68 (9)
C4—C5—H5B	109.5	C21—C15—N3	116.42 (9)
H5A—C5—H5B	109.5	C17—C16—C15	121.93 (10)
C4—C5—H5C	109.5	C17—C16—H16	119.0
H5A—C5—H5C	109.5	C15—C16—H16	119.0
H5B—C5—H5C	109.5	C16—C17—C19	117.90 (10)
C4—C6—C7	121.31 (10)	C16—C17—C18	120.18 (10)
C4—C6—H6	119.3	C19—C17—C18	121.92 (10)
C7—C6—H6	119.3	C17—C18—H18A	109.5
C6—C7—C1	118.89 (10)	C17—C18—H18B	109.5
C6—C7—N1	126.84 (10)	H18A—C18—H18B	109.5
C1—C7—N1	114.20 (10)	C17—C18—H18C	109.5
C8—N1—C7	121.58 (10)	H18A—C18—H18C	109.5
N1—C8—C9	121.61 (10)	H18B—C18—H18C	109.5
N1—C8—H8	119.2	C20—C19—C17	121.49 (10)
C9—C8—H8	119.2	C20—C19—H19	119.3
N2—C9—C10	123.29 (10)	C17—C19—H19	119.3
N2—C9—C8	114.60 (9)	C19—C20—C21	120.05 (10)
C10—C9—C8	122.07 (10)	C19—C20—H20	120.0
C11—C10—C9	118.58 (10)	C21—C20—H20	120.0
C11—C10—H10	120.7	O2—C21—C20	118.06 (9)
C9—C10—H10	120.7	O2—C21—C15	122.20 (10)
C10—C11—C12	118.84 (10)	C20—C21—C15	119.72 (9)
C10—C11—H11	120.6	C21—O2—H2A	112.5 (10)
O1—C1—C2—C3	178.93 (11)	C11—C12—C13—C14	179.63 (10)
C7—C1—C2—C3	−0.42 (18)	C10—C9—N2—C13	−1.22 (16)
C1—C2—C3—C4	−0.16 (18)	C8—C9—N2—C13	176.55 (9)
C2—C3—C4—C6	0.66 (18)	C12—C13—N2—C9	1.05 (15)
C2—C3—C4—C5	−176.69 (12)	C14—C13—N2—C9	−178.70 (9)
C3—C4—C6—C7	−0.61 (17)	N2—C13—C14—N3	−15.80 (16)
C5—C4—C6—C7	176.73 (11)	C12—C13—C14—N3	164.44 (11)
C4—C6—C7—C1	0.06 (17)	C13—C14—N3—C15	−177.17 (9)
C4—C6—C7—N1	−176.84 (11)	C14—N3—C15—C16	16.85 (16)
O1—C1—C7—C6	−178.88 (10)	C14—N3—C15—C21	−164.27 (10)
C2—C1—C7—C6	0.47 (17)	C21—C15—C16—C17	1.35 (16)
O1—C1—C7—N1	−1.61 (16)	N3—C15—C16—C17	−179.79 (10)
C2—C1—C7—N1	177.74 (10)	C15—C16—C17—C19	−0.49 (16)
C6—C7—N1—C8	−3.83 (18)	C15—C16—C17—C18	−179.90 (10)
C1—C7—N1—C8	179.15 (10)	C16—C17—C19—C20	−0.50 (16)
C7—N1—C8—C9	176.17 (10)	C18—C17—C19—C20	178.90 (10)
N1—C8—C9—N2	176.83 (10)	C17—C19—C20—C21	0.60 (17)
N1—C8—C9—C10	−5.37 (17)	C19—C20—C21—O2	178.48 (10)
N2—C9—C10—C11	0.45 (17)	C19—C20—C21—C15	0.29 (16)
C8—C9—C10—C11	−177.16 (10)	C16—C15—C21—O2	−179.34 (10)
C9—C10—C11—C12	0.52 (17)	N3—C15—C21—O2	1.71 (15)
C10—C11—C12—C13	−0.68 (17)	C16—C15—C21—C20	−1.24 (15)
C11—C12—C13—N2	−0.12 (17)	N3—C15—C21—C20	179.82 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.836 (17)	1.960 (17)	2.7592 (12)	159.6 (15)
O2—H2A···N3	0.836 (17)	2.347 (15)	2.7624 (12)	111.3 (12)
O1—H1A···N1	0.86 (2)	2.120 (19)	2.6722 (13)	121.7 (16)
O3—H3D···N2	0.812 (16)	2.187 (16)	2.9865 (12)	168.0 (16)
O3—H3D···N3	0.812 (16)	2.569 (16)	3.0142 (9)	115.9 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.836 (17)	1.960 (17)	2.7592 (12)	159.6 (15)
O2—H2A⋯N3	0.836 (17)	2.347 (15)	2.7624 (12)	111.3 (12)
O1—H1A⋯N1	0.86 (2)	2.120 (19)	2.6722 (13)	121.7 (16)
O3—H3D⋯N2	0.812 (16)	2.187 (16)	2.9865 (12)	168.0 (16)
O3—H3D⋯N3	0.812 (16)	2.569 (16)	3.0142 (9)	115.9 (14)