N-[(E)-4-Pyridylmethyl-ene]-4-[(E)-4-(4-pyridylmethyl-eneamino)benz-yl]aniline tetra-hydrate.

The title compound, C(25)H(20)N(4)·4H(2)O, crystallizes with the organic mol-ecule lying on a twofold rotation axis through the methyl-ene bridge C atom; there are also two water molecules in the asymmetric unit. The crystal structure is stabilized by C-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, linking the water mol-ecules to each other and to the pyridine N atom.

Related literature

For related literature, see: Jursic et al. (2002 ▶); Coucouvanis et al. (1993 ▶); Hodnett & Mooney (1970 ▶); Li et al. (2005 ▶); Yam & Pui (2002 ▶).

Experimental

Crystal data

C25H20N4·4H2O

M = 448.51

Monoclinic,

a = 17.7743 (14) Å

b = 4.7309 (4) Å

c = 28.478 (2) Å

β = 99.69 (1)°

V = 2360.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

7552 measured reflections

2302 independent reflections

1850 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.158

S = 1.08

2302 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Sheldrick, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063179/sf2014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063179/sf2014Isup2.hkl

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

C25H20N4·4H2O1	F000 = 952
Mr = 448.51	Dx = 1.262 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2/c	Cell parameters from 2376 reflections
a = 17.7743 (14) Å	θ = 2.3–27.4º
b = 4.7309 (4) Å	µ = 0.09 mm−1
c = 28.478 (2) Å	T = 294 (2) K
β = 99.69 (1)º	Block, yellow
V = 2360.5 (3) Å3	0.40 × 0.30 × 0.30 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1850 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Monochromator: graphite	θmax = 26.0º
T = 294(2) K	θmin = 2.3º
phi and ω scans	h = −13→21
Absorption correction: none	k = −5→5
7552 measured reflections	l = −35→35
2302 independent reflections

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0751P)2 + 1.2009P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2302 reflections	Δρmax = 0.20 e Å−3
162 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)
C1	0.5000	0.9902 (5)	0.2500	0.0468 (6)
H1A	0.4695	1.1104	0.2266	0.056*	0.50
H1B	0.5305	1.1104	0.2734	0.056*	0.50
C2	0.44833 (9)	0.8053 (3)	0.27406 (6)	0.0400 (4)
C3	0.47436 (10)	0.6805 (4)	0.31775 (6)	0.0493 (5)
H3	0.5231	0.7234	0.3336	0.059*
C4	0.42989 (11)	0.4944 (4)	0.33839 (7)	0.0504 (5)
H4	0.4487	0.4148	0.3679	0.060*
C5	0.35682 (10)	0.4251 (4)	0.31521 (6)	0.0419 (4)
C6	0.32993 (10)	0.5543 (4)	0.27215 (6)	0.0456 (4)
H6	0.2808	0.5141	0.2565	0.055*
C7	0.37470 (10)	0.7423 (4)	0.25190 (6)	0.0449 (4)
H7	0.3551	0.8276	0.2230	0.054*
C8	0.32973 (11)	0.0807 (4)	0.36783 (7)	0.0511 (5)
H8	0.3811	0.0887	0.3814	0.061*
C9	0.27972 (11)	−0.1144 (4)	0.38837 (6)	0.0492 (5)
C10	0.30718 (14)	−0.2665 (5)	0.42886 (8)	0.0658 (6)
H10	0.3578	−0.2467	0.4435	0.079*
C11	0.25914 (16)	−0.4484 (5)	0.44754 (9)	0.0739 (7)
H11	0.2788	−0.5490	0.4749	0.089*
C12	0.16076 (14)	−0.3398 (6)	0.38962 (10)	0.0770 (7)
H12	0.1098	−0.3633	0.3759	0.092*
C13	0.20413 (12)	−0.1544 (5)	0.36816 (8)	0.0642 (6)
H13	0.1830	−0.0579	0.3406	0.077*
N1	0.30633 (9)	0.2361 (3)	0.33305 (5)	0.0481 (4)
N2	0.18689 (13)	−0.4874 (4)	0.42866 (8)	0.0748 (6)
O1	0.49404 (13)	0.2296 (5)	0.45062 (7)	0.0944 (7)
H1C	0.472 (2)	0.249 (8)	0.4769 (14)	0.142*
H1D	0.521 (2)	0.065 (9)	0.4559 (14)	0.142*
O2	0.42372 (14)	0.2747 (5)	0.53161 (9)	0.1114 (8)
H2A	0.442 (3)	0.440 (11)	0.5419 (15)	0.167*
H2B	0.386 (3)	0.219 (10)	0.5448 (16)	0.167*

	U11	U22	U33	U12	U13	U23
C1	0.0515 (15)	0.0357 (13)	0.0585 (15)	0.000	0.0250 (12)	0.000
C2	0.0424 (9)	0.0319 (8)	0.0501 (10)	0.0024 (7)	0.0206 (7)	−0.0036 (7)
C3	0.0425 (10)	0.0537 (11)	0.0523 (10)	−0.0080 (8)	0.0102 (8)	−0.0007 (8)
C4	0.0506 (11)	0.0545 (11)	0.0463 (10)	−0.0080 (9)	0.0091 (8)	0.0062 (8)
C5	0.0434 (10)	0.0382 (9)	0.0481 (10)	−0.0037 (7)	0.0190 (7)	−0.0058 (7)
C6	0.0384 (9)	0.0460 (10)	0.0528 (10)	−0.0032 (8)	0.0089 (7)	−0.0003 (8)
C7	0.0458 (10)	0.0424 (10)	0.0487 (10)	0.0049 (8)	0.0140 (8)	0.0042 (7)
C8	0.0493 (11)	0.0475 (10)	0.0589 (11)	−0.0087 (8)	0.0159 (9)	−0.0010 (9)
C9	0.0597 (12)	0.0397 (10)	0.0530 (11)	−0.0085 (8)	0.0237 (9)	−0.0064 (8)
C10	0.0730 (14)	0.0611 (13)	0.0651 (13)	−0.0125 (11)	0.0167 (11)	0.0066 (10)
C11	0.0983 (19)	0.0629 (14)	0.0663 (14)	−0.0161 (13)	0.0303 (13)	0.0112 (11)
C12	0.0674 (14)	0.0750 (16)	0.0933 (18)	−0.0255 (12)	0.0271 (13)	0.0000 (14)
C13	0.0630 (13)	0.0626 (13)	0.0695 (14)	−0.0158 (11)	0.0179 (10)	0.0047 (10)
N1	0.0490 (9)	0.0456 (9)	0.0527 (9)	−0.0083 (7)	0.0173 (7)	0.0003 (7)
N2	0.0899 (15)	0.0609 (12)	0.0839 (14)	−0.0222 (11)	0.0440 (12)	−0.0001 (10)
O1	0.1031 (15)	0.1013 (15)	0.0787 (12)	−0.0129 (12)	0.0153 (10)	0.0224 (11)
O2	0.1177 (18)	0.0957 (16)	0.1373 (19)	−0.0295 (13)	0.0691 (15)	0.0062 (13)

C1—C2i	1.513 (2)	C8—C9	1.469 (3)
C1—C2	1.513 (2)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.377 (3)
C1—H1B	0.9700	C9—C13	1.383 (3)
C2—C3	1.385 (3)	C10—C11	1.380 (3)
C2—C7	1.386 (3)	C10—H10	0.9300
C3—C4	1.379 (2)	C11—N2	1.319 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.393 (3)	C12—N2	1.329 (3)
C4—H4	0.9300	C12—C13	1.377 (3)
C5—C6	1.382 (2)	C12—H12	0.9300
C5—N1	1.420 (2)	C13—H13	0.9300
C6—C7	1.382 (2)	O1—H1C	0.91 (4)
C6—H6	0.9300	O1—H1D	0.91 (4)
C7—H7	0.9300	O2—H2A	0.88 (5)
C8—N1	1.247 (2)	O2—H2B	0.87 (5)
C2i—C1—C2	109.37 (19)	C2—C7—H7	119.5
C2i—C1—H1A	109.8	N1—C8—C9	122.89 (18)
C2—C1—H1A	109.8	N1—C8—H8	118.6
C2i—C1—H1B	109.8	C9—C8—H8	118.6
C2—C1—H1B	109.8	C10—C9—C13	117.36 (18)
H1A—C1—H1B	108.2	C10—C9—C8	120.58 (19)
C3—C2—C7	117.66 (16)	C13—C9—C8	122.06 (18)
C3—C2—C1	121.12 (14)	C9—C10—C11	119.6 (2)
C7—C2—C1	121.11 (14)	C9—C10—H10	120.2
C4—C3—C2	121.77 (17)	C11—C10—H10	120.2
C4—C3—H3	119.1	N2—C11—C10	123.6 (2)
C2—C3—H3	119.1	N2—C11—H11	118.2
C3—C4—C5	120.24 (17)	C10—C11—H11	118.2
C3—C4—H4	119.9	N2—C12—C13	124.3 (2)
C5—C4—H4	119.9	N2—C12—H12	117.9
C6—C5—C4	118.18 (16)	C13—C12—H12	117.9
C6—C5—N1	116.81 (15)	C12—C13—C9	118.7 (2)
C4—C5—N1	124.99 (16)	C12—C13—H13	120.7
C5—C6—C7	121.16 (16)	C9—C13—H13	120.7
C5—C6—H6	119.4	C8—N1—C5	120.59 (16)
C7—C6—H6	119.4	C11—N2—C12	116.53 (19)
C6—C7—C2	120.95 (16)	H1C—O1—H1D	104 (3)
C6—C7—H7	119.5	H2A—O2—H2B	113 (4)
C2i—C1—C2—C3	79.47 (15)	N1—C8—C9—C13	5.0 (3)
C2i—C1—C2—C7	−96.86 (15)	C13—C9—C10—C11	−0.3 (3)
C7—C2—C3—C4	1.5 (3)	C8—C9—C10—C11	179.97 (19)
C1—C2—C3—C4	−174.93 (16)	C9—C10—C11—N2	0.1 (4)
C2—C3—C4—C5	0.5 (3)	N2—C12—C13—C9	−0.7 (4)
C3—C4—C5—C6	−2.0 (3)	C10—C9—C13—C12	0.6 (3)
C3—C4—C5—N1	179.84 (16)	C8—C9—C13—C12	−179.7 (2)
C4—C5—C6—C7	1.5 (3)	C9—C8—N1—C5	178.70 (15)
N1—C5—C6—C7	179.84 (15)	C6—C5—N1—C8	169.49 (17)
C5—C6—C7—C2	0.5 (3)	C4—C5—N1—C8	−12.3 (3)
C3—C2—C7—C6	−2.0 (2)	C10—C11—N2—C12	−0.1 (4)
C1—C2—C7—C6	174.46 (16)	C13—C12—N2—C11	0.5 (4)
N1—C8—C9—C10	−175.31 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.52	3.443 (3)	175
O1—H1C···O2	0.91 (4)	1.90 (4)	2.810 (3)	178 (4)
O2—H2B···N2ii	0.87 (5)	1.94 (5)	2.782 (3)	163 (4)
O2—H2A···O1iii	0.88 (5)	1.93 (5)	2.765 (3)	160 (4)
O1—H1D···O2iv	0.91 (4)	1.88 (4)	2.799 (3)	178 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.52	3.443 (3)	175
O1—H1C⋯O2	0.91 (4)	1.90 (4)	2.810 (3)	178 (4)
O2—H2B⋯N2i	0.87 (5)	1.94 (5)	2.782 (3)	163 (4)
O2—H2A⋯O1ii	0.88 (5)	1.93 (5)	2.765 (3)	160 (4)
O1—H1D⋯O2iii	0.91 (4)	1.88 (4)	2.799 (3)	178 (4)

Symmetry codes: (i) ; (ii) ; (iii) .