6,6'-Dimeth-oxy-2,2'-[4,5-dimethyl-o-phenyl-enebis(nitrilo-methyl-idyne)]diphenol monohydrate.

In the title compound, C(24)H(24)N(2)O(4)·H(2)O, the dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 65.06 (9) and 3.02 (9)°. Strong intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs. The H atoms of the water mol-ecule act as donors in the formation of bifurcated O-H⋯(O,O) inter-molecular hydrogen bonds with the O atoms of the hydr-oxy and meth-oxy groups with R(1) (2)(5) ring motifs; these may influence the mol-ecular conformation.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Cakir et al. (2002 ▶); Eltayeb & Ahmed (2005 ▶); Eltayeb et al. (2007 ▶); Kargar et al. (2009 ▶). For background to the applications of Schiff base ligands as thermochromic and photochromic materials, see: Hajioudis et al. (1987 ▶).

Experimental

Crystal data

C24H24N2O4·H2O

M = 422.47

Triclinic,

a = 8.7431 (5) Å

b = 10.3049 (6) Å

c = 13.6614 (7) Å

α = 69.556 (3)°

β = 83.846 (3)°

γ = 70.280 (3)°

V = 1085.6 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.987

23270 measured reflections

5369 independent reflections

2912 reflections with I > 2I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.141

S = 1.01

5369 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002916/lh2982sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002916/lh2982Isup2.hkl

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

C24H24N2O4·H2O	Z = 2
Mr = 422.47	F(000) = 448
Triclinic, P1	Dx = 1.292 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7431 (5) Å	Cell parameters from 5124 reflections
b = 10.3049 (6) Å	θ = 2.2–25.0°
c = 13.6614 (7) Å	µ = 0.09 mm−1
α = 69.556 (3)°	T = 296 K
β = 83.846 (3)°	Block, yellow
γ = 70.280 (3)°	0.30 × 0.20 × 0.15 mm
V = 1085.6 (1) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5369 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2˘I)
graphite	Rint = 0.031
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.973, Tmax = 0.987	k = −12→13
23270 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) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1326P] where P = (Fo2 + 2Fc2)/3
5369 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.20 e Å−3
0 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	0.48196 (13)	0.46281 (13)	0.27727 (9)	0.0574 (3)
H1	0.5531	0.4027	0.3362	0.086*
O2	0.58907 (14)	0.10375 (12)	0.31399 (9)	0.0563 (3)
H2	0.6463	0.1102	0.3678	0.084*
O3	0.34071 (17)	0.62867 (15)	0.09838 (10)	0.0749 (4)
O4	0.45471 (16)	0.01221 (14)	0.20011 (10)	0.0692 (4)
N1	0.74540 (15)	0.32782 (13)	0.39027 (10)	0.0436 (3)
N2	0.74691 (15)	0.04912 (14)	0.47979 (10)	0.0438 (3)
C1	0.5789 (2)	0.51020 (17)	0.19880 (12)	0.0465 (4)
C2	0.5055 (2)	0.59934 (18)	0.10105 (13)	0.0549 (5)
C3	0.5987 (3)	0.6496 (2)	0.01908 (14)	0.0687 (6)
H3A	0.5502	0.7081	−0.0459	0.082*
C4	0.7642 (3)	0.6143 (2)	0.03171 (15)	0.0733 (6)
H4A	0.8262	0.6484	−0.0249	0.088*
C5	0.8378 (2)	0.5294 (2)	0.12719 (14)	0.0630 (5)
H5A	0.9489	0.5076	0.1354	0.076*
C6	0.7458 (2)	0.47583 (17)	0.21197 (12)	0.0469 (4)
C7	0.8237 (2)	0.38539 (17)	0.31301 (13)	0.0466 (4)
H7A	0.9335	0.3692	0.3214	0.056*
C8	0.82177 (17)	0.24595 (16)	0.48957 (11)	0.0401 (4)
C9	0.88484 (19)	0.30867 (18)	0.54329 (13)	0.0475 (4)
H9A	0.8844	0.4046	0.5110	0.057*
C10	0.94858 (19)	0.2329 (2)	0.64369 (13)	0.0496 (4)
C11	0.95310 (19)	0.0878 (2)	0.69018 (12)	0.0507 (4)
C12	0.88856 (19)	0.02546 (18)	0.63693 (12)	0.0493 (4)
H12A	0.8914	−0.0712	0.6685	0.059*
C13	0.81949 (17)	0.10333 (17)	0.53748 (12)	0.0410 (4)
C14	0.74023 (18)	−0.08139 (17)	0.51154 (13)	0.0467 (4)
H14A	0.7864	−0.1459	0.5759	0.056*
C15	0.66348 (18)	−0.13050 (17)	0.45037 (13)	0.0455 (4)
C16	0.6581 (2)	−0.27411 (18)	0.48757 (15)	0.0563 (5)
H16A	0.7039	−0.3370	0.5524	0.068*
C17	0.5870 (2)	−0.32238 (19)	0.43002 (16)	0.0605 (5)
H17A	0.5842	−0.4179	0.4556	0.073*
C18	0.5181 (2)	−0.2296 (2)	0.33301 (16)	0.0589 (5)
H18A	0.4699	−0.2637	0.2940	0.071*
C19	0.5206 (2)	−0.08833 (19)	0.29418 (14)	0.0517 (4)
C20	0.59181 (18)	−0.03598 (17)	0.35303 (13)	0.0458 (4)
C21	0.2574 (3)	0.7227 (2)	0.00270 (16)	0.0918 (8)
H21A	0.1438	0.7335	0.0106	0.138*
H21B	0.3006	0.6814	−0.0514	0.138*
H21C	0.2715	0.8168	−0.0157	0.138*
C22	0.4007 (3)	−0.0392 (3)	0.13155 (17)	0.0840 (7)
H22A	0.3546	0.0412	0.0697	0.126*
H22B	0.3198	−0.0834	0.1654	0.126*
H22C	0.4908	−0.1104	0.1129	0.126*
C23	1.0072 (2)	0.3092 (2)	0.70012 (15)	0.0693 (6)
H23A	0.9946	0.4077	0.6554	0.104*
H23B	1.1198	0.2580	0.7188	0.104*
H23C	0.9447	0.3106	0.7622	0.104*
C24	1.0284 (2)	−0.0036 (3)	0.79731 (14)	0.0789 (7)
H24A	0.9768	0.0447	0.8466	0.118*
H24B	1.1423	−0.0157	0.7950	0.118*
H24C	1.0137	−0.0977	0.8183	0.118*
O1W	0.25045 (16)	0.32247 (16)	0.23580 (10)	0.0795 (4)
H1W	0.2953	0.4012	0.2238	0.119*
H2W	0.3547	0.2463	0.2467	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0557 (7)	0.0600 (8)	0.0444 (7)	−0.0177 (6)	−0.0123 (6)	−0.0001 (6)
O2	0.0718 (8)	0.0398 (7)	0.0541 (7)	−0.0176 (6)	−0.0099 (6)	−0.0094 (5)
O3	0.0744 (9)	0.0733 (9)	0.0556 (8)	−0.0061 (7)	−0.0298 (7)	−0.0043 (7)
O4	0.0853 (9)	0.0595 (8)	0.0662 (9)	−0.0225 (7)	−0.0143 (7)	−0.0214 (7)
N1	0.0496 (8)	0.0390 (7)	0.0354 (7)	−0.0115 (6)	−0.0089 (6)	−0.0044 (6)
N2	0.0436 (7)	0.0394 (8)	0.0416 (8)	−0.0102 (6)	0.0013 (6)	−0.0088 (6)
C1	0.0625 (10)	0.0373 (9)	0.0362 (9)	−0.0140 (8)	−0.0068 (8)	−0.0078 (7)
C2	0.0712 (12)	0.0433 (10)	0.0424 (10)	−0.0082 (9)	−0.0148 (9)	−0.0104 (8)
C3	0.1010 (17)	0.0537 (12)	0.0371 (10)	−0.0130 (11)	−0.0127 (10)	−0.0058 (9)
C4	0.0947 (17)	0.0735 (14)	0.0409 (11)	−0.0281 (12)	0.0079 (10)	−0.0076 (10)
C5	0.0733 (12)	0.0650 (12)	0.0466 (11)	−0.0248 (10)	0.0049 (9)	−0.0125 (9)
C6	0.0592 (10)	0.0412 (9)	0.0377 (9)	−0.0143 (8)	−0.0039 (8)	−0.0108 (7)
C7	0.0499 (9)	0.0434 (9)	0.0439 (10)	−0.0111 (8)	−0.0065 (8)	−0.0130 (8)
C8	0.0354 (8)	0.0404 (9)	0.0347 (8)	−0.0052 (6)	−0.0040 (6)	−0.0064 (7)
C9	0.0458 (9)	0.0467 (10)	0.0458 (10)	−0.0111 (7)	−0.0050 (7)	−0.0125 (8)
C10	0.0394 (9)	0.0627 (11)	0.0426 (9)	−0.0089 (8)	−0.0027 (7)	−0.0192 (9)
C11	0.0405 (9)	0.0648 (12)	0.0348 (9)	−0.0055 (8)	−0.0033 (7)	−0.0123 (8)
C12	0.0457 (9)	0.0437 (9)	0.0400 (9)	−0.0032 (7)	−0.0007 (7)	−0.0026 (7)
C13	0.0352 (8)	0.0433 (9)	0.0363 (8)	−0.0057 (7)	−0.0001 (6)	−0.0099 (7)
C14	0.0420 (9)	0.0428 (10)	0.0437 (9)	−0.0084 (7)	0.0034 (7)	−0.0064 (8)
C15	0.0383 (8)	0.0391 (9)	0.0527 (10)	−0.0088 (7)	0.0081 (7)	−0.0132 (8)
C16	0.0506 (10)	0.0421 (10)	0.0660 (12)	−0.0133 (8)	0.0086 (9)	−0.0099 (9)
C17	0.0549 (11)	0.0407 (10)	0.0834 (14)	−0.0200 (8)	0.0131 (10)	−0.0169 (10)
C18	0.0511 (10)	0.0542 (11)	0.0801 (14)	−0.0199 (9)	0.0106 (10)	−0.0329 (11)
C19	0.0472 (9)	0.0464 (10)	0.0590 (11)	−0.0115 (8)	0.0041 (8)	−0.0190 (9)
C20	0.0415 (9)	0.0387 (9)	0.0554 (10)	−0.0116 (7)	0.0079 (8)	−0.0171 (8)
C21	0.1047 (17)	0.0766 (15)	0.0687 (14)	0.0037 (13)	−0.0514 (13)	−0.0104 (12)
C22	0.1109 (18)	0.0963 (17)	0.0642 (14)	−0.0490 (14)	0.0015 (12)	−0.0350 (13)
C23	0.0644 (12)	0.0936 (16)	0.0568 (12)	−0.0233 (11)	−0.0064 (9)	−0.0333 (11)
C24	0.0728 (13)	0.0990 (17)	0.0419 (11)	−0.0162 (12)	−0.0161 (9)	−0.0021 (11)
O1W	0.0693 (9)	0.0887 (11)	0.0677 (9)	−0.0254 (8)	−0.0075 (7)	−0.0086 (8)

O1—C1	1.3511 (19)	C11—C12	1.385 (2)
O1—H1	0.9574	C11—C24	1.512 (2)
O2—C20	1.3422 (18)	C12—C13	1.394 (2)
O2—H2	0.9642	C12—H12A	0.9300
O3—C2	1.371 (2)	C14—C15	1.432 (2)
O3—C21	1.422 (2)	C14—H14A	0.9300
O4—C19	1.372 (2)	C15—C16	1.402 (2)
O4—C22	1.411 (2)	C15—C20	1.404 (2)
N1—C7	1.271 (2)	C16—C17	1.356 (3)
N1—C8	1.4186 (18)	C16—H16A	0.9300
N2—C14	1.281 (2)	C17—C18	1.389 (3)
N2—C13	1.411 (2)	C17—H17A	0.9300
C1—C6	1.396 (2)	C18—C19	1.372 (2)
C1—C2	1.403 (2)	C18—H18A	0.9300
C2—C3	1.367 (3)	C19—C20	1.401 (2)
C3—C4	1.382 (3)	C21—H21A	0.9600
C3—H3A	0.9300	C21—H21B	0.9600
C4—C5	1.373 (3)	C21—H21C	0.9600
C4—H4A	0.9300	C22—H22A	0.9600
C5—C6	1.395 (2)	C22—H22B	0.9600
C5—H5A	0.9300	C22—H22C	0.9600
C6—C7	1.453 (2)	C23—H23A	0.9600
C7—H7A	0.9300	C23—H23B	0.9600
C8—C9	1.385 (2)	C23—H23C	0.9600
C8—C13	1.391 (2)	C24—H24A	0.9600
C9—C10	1.387 (2)	C24—H24B	0.9600
C9—H9A	0.9300	C24—H24C	0.9600
C10—C11	1.394 (2)	O1W—H1W	0.9731
C10—C23	1.502 (2)	O1W—H2W	0.9664
C1—O1—H1	105.3	N2—C14—H14A	119.2
C20—O2—H2	101.6	C15—C14—H14A	119.2
C2—O3—C21	117.48 (16)	C16—C15—C20	119.09 (16)
C19—O4—C22	117.25 (15)	C16—C15—C14	120.16 (16)
C7—N1—C8	120.70 (13)	C20—C15—C14	120.75 (15)
C14—N2—C13	123.85 (14)	C17—C16—C15	120.75 (17)
O1—C1—C6	122.82 (14)	C17—C16—H16A	119.6
O1—C1—C2	117.44 (16)	C15—C16—H16A	119.6
C6—C1—C2	119.74 (16)	C16—C17—C18	120.21 (17)
C3—C2—O3	125.95 (16)	C16—C17—H17A	119.9
C3—C2—C1	119.61 (18)	C18—C17—H17A	119.9
O3—C2—C1	114.44 (16)	C19—C18—C17	120.71 (18)
C2—C3—C4	120.71 (17)	C19—C18—H18A	119.6
C2—C3—H3A	119.6	C17—C18—H18A	119.6
C4—C3—H3A	119.6	C18—C19—O4	125.26 (17)
C5—C4—C3	120.52 (19)	C18—C19—C20	119.90 (17)
C5—C4—H4A	119.7	O4—C19—C20	114.83 (15)
C3—C4—H4A	119.7	O2—C20—C19	118.51 (15)
C4—C5—C6	119.97 (19)	O2—C20—C15	122.17 (15)
C4—C5—H5A	120.0	C19—C20—C15	119.32 (15)
C6—C5—H5A	120.0	O3—C21—H21A	109.5
C5—C6—C1	119.44 (15)	O3—C21—H21B	109.5
C5—C6—C7	120.03 (16)	H21A—C21—H21B	109.5
C1—C6—C7	120.54 (15)	O3—C21—H21C	109.5
N1—C7—C6	121.65 (15)	H21A—C21—H21C	109.5
N1—C7—H7A	119.2	H21B—C21—H21C	109.5
C6—C7—H7A	119.2	O4—C22—H22A	109.5
C9—C8—C13	119.56 (14)	O4—C22—H22B	109.5
C9—C8—N1	121.60 (14)	H22A—C22—H22B	109.5
C13—C8—N1	118.58 (14)	O4—C22—H22C	109.5
C8—C9—C10	122.06 (16)	H22A—C22—H22C	109.5
C8—C9—H9A	119.0	H22B—C22—H22C	109.5
C10—C9—H9A	119.0	C10—C23—H23A	109.5
C9—C10—C11	118.54 (16)	C10—C23—H23B	109.5
C9—C10—C23	119.63 (17)	H23A—C23—H23B	109.5
C11—C10—C23	121.82 (15)	C10—C23—H23C	109.5
C12—C11—C10	119.41 (14)	H23A—C23—H23C	109.5
C12—C11—C24	119.24 (17)	H23B—C23—H23C	109.5
C10—C11—C24	121.35 (17)	C11—C24—H24A	109.5
C11—C12—C13	121.97 (16)	C11—C24—H24B	109.5
C11—C12—H12A	119.0	H24A—C24—H24B	109.5
C13—C12—H12A	119.0	C11—C24—H24C	109.5
C8—C13—C12	118.37 (15)	H24A—C24—H24C	109.5
C8—C13—N2	116.34 (13)	H24B—C24—H24C	109.5
C12—C13—N2	125.28 (15)	H1W—O1W—H2W	95.0
N2—C14—C15	121.63 (15)
C21—O3—C2—C3	−1.7 (3)	C10—C11—C12—C13	0.3 (2)
C21—O3—C2—C1	177.79 (17)	C24—C11—C12—C13	−179.15 (15)
O1—C1—C2—C3	−179.75 (16)	C9—C8—C13—C12	−3.1 (2)
C6—C1—C2—C3	1.2 (3)	N1—C8—C13—C12	−177.31 (14)
O1—C1—C2—O3	0.7 (2)	C9—C8—C13—N2	177.27 (13)
C6—C1—C2—O3	−178.33 (15)	N1—C8—C13—N2	3.0 (2)
O3—C2—C3—C4	178.97 (18)	C11—C12—C13—C8	2.5 (2)
C1—C2—C3—C4	−0.5 (3)	C11—C12—C13—N2	−177.89 (14)
C2—C3—C4—C5	−0.7 (3)	C14—N2—C13—C8	177.54 (14)
C3—C4—C5—C6	1.1 (3)	C14—N2—C13—C12	−2.1 (2)
C4—C5—C6—C1	−0.4 (3)	C13—N2—C14—C15	179.30 (14)
C4—C5—C6—C7	179.75 (18)	N2—C14—C15—C16	−179.90 (15)
O1—C1—C6—C5	−179.76 (16)	N2—C14—C15—C20	−0.3 (2)
C2—C1—C6—C5	−0.7 (2)	C20—C15—C16—C17	1.0 (2)
O1—C1—C6—C7	0.1 (2)	C14—C15—C16—C17	−179.45 (16)
C2—C1—C6—C7	179.11 (15)	C15—C16—C17—C18	0.0 (3)
C8—N1—C7—C6	−176.84 (14)	C16—C17—C18—C19	−0.2 (3)
C5—C6—C7—N1	−175.85 (16)	C17—C18—C19—O4	−179.23 (16)
C1—C6—C7—N1	4.3 (2)	C17—C18—C19—C20	−0.6 (3)
C7—N1—C8—C9	61.2 (2)	C22—O4—C19—C18	−9.5 (3)
C7—N1—C8—C13	−124.72 (17)	C22—O4—C19—C20	171.84 (16)
C13—C8—C9—C10	0.9 (2)	C18—C19—C20—O2	−178.50 (15)
N1—C8—C9—C10	174.99 (14)	O4—C19—C20—O2	0.3 (2)
C8—C9—C10—C11	1.9 (2)	C18—C19—C20—C15	1.5 (2)
C8—C9—C10—C23	−176.79 (15)	O4—C19—C20—C15	−179.69 (14)
C9—C10—C11—C12	−2.5 (2)	C16—C15—C20—O2	178.33 (14)
C23—C10—C11—C12	176.17 (15)	C14—C15—C20—O2	−1.3 (2)
C9—C10—C11—C24	176.97 (16)	C16—C15—C20—C19	−1.7 (2)
C23—C10—C11—C24	−4.4 (3)	C14—C15—C20—C19	178.70 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.96	1.72	2.5929 (18)	150
O1W—H1W···O1	0.97	2.21	3.050 (2)	144
O1W—H1W···O3	0.97	2.50	3.366 (2)	148
O2—H2···N2	0.96	1.66	2.5704 (18)	156
O1W—H2W···O2	0.97	2.15	3.079 (2)	160
O1W—H2W···O4	0.97	2.55	3.271 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.96	1.72	2.5929 (18)	150
O2—H2⋯N2	0.96	1.66	2.5704 (18)	156
O1W—H1W⋯O1	0.97	2.21	3.050 (2)	144
O1W—H1W⋯O3	0.97	2.50	3.366 (2)	148
O1W—H2W⋯O2	0.97	2.15	3.079 (2)	160
O1W—H2W⋯O4	0.97	2.55	3.271 (2)	131