N,N'-p-Phenyl-enediisonicotinamide monohydrate.

The organic mol-ecule of the title compound, C(18)H(14)N(4)O(2)·H(2)O, lies on a center of inversion located at the centre of the central phenyl-ene ring. There are two half-molecules in the asymmetric unit. In the crystal, the mol-ecules are linked through by N-H⋯O and O-H⋯N hydrogen bonds involving the water mol-ecule, forming a layer structure. The layers inter-act by π-π inter-actions between the aromatic rings.

Related literature

For background to N,N′-p-phenylenediisonicotinamide complexes, see: Burchell et al. (2003 ▶, 2004 ▶); Niu et al. (2004 ▶); Pansanel et al. (2006 ▶).

Experimental

Crystal data

C18H14N4O2·H2O

M = 336.35

Triclinic,

a = 6.9936 (14) Å

b = 10.852 (2) Å

c = 11.285 (2) Å

α = 95.98 (3)°

β = 106.36 (3)°

γ = 94.68 (3)°

V = 811.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.32 × 0.21 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004 ▶) T min = 0.976, T max = 0.987

7994 measured reflections

3671 independent reflections

1782 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.163

S = 1.10

3671 reflections

235 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 I, global. DOI: 10.1107/S1600536809024684/ng2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024684/ng2603Isup2.hkl

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

C18H14N4O2·H2O	Z = 2
Mr = 336.35	F(000) = 352
Triclinic, P1	Dx = 1.376 Mg m−3
a = 6.9936 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.852 (2) Å	θ = 3.1–27.5°
c = 11.285 (2) Å	µ = 0.10 mm−1
α = 95.98 (3)°	T = 296 K
β = 106.36 (3)°	Block, colorless
γ = 94.68 (3)°	0.32 × 0.21 × 0.13 mm
V = 811.8 (3) Å3

Rigaku R-AXIS RAPID diffractometer	3671 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.039
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004)	h = −9→8
Tmin = 0.976, Tmax = 0.987	k = −14→13
7994 measured reflections	l = −14→14

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3671 reflections	Δρmax = 0.24 e Å−3
235 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (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
O1	0.5143 (3)	0.75658 (16)	0.44339 (18)	0.0695 (6)
N1	0.3107 (4)	0.4128 (2)	0.0888 (2)	0.0784 (8)
C1	0.2062 (5)	0.4882 (3)	0.1391 (3)	0.0791 (9)
H1	0.0645	0.4691	0.1150	0.095*
O2	0.1628 (3)	0.77553 (17)	0.78063 (19)	0.0773 (6)
N2	0.7556 (3)	0.79239 (16)	0.34696 (18)	0.0511 (5)
H2A	0.7946	0.7654	0.2822	0.061*
C2	0.2908 (4)	0.5924 (2)	0.2241 (3)	0.0667 (7)
H2	0.2090	0.6436	0.2569	0.080*
O3	0.1253 (3)	0.2348 (2)	−0.12516 (19)	0.0774 (7)
N3	0.7983 (4)	1.0595 (2)	0.8737 (2)	0.0693 (7)
C3	0.4971 (4)	0.6211 (2)	0.2608 (2)	0.0507 (6)
N4	0.2782 (3)	0.70930 (17)	0.61858 (19)	0.0545 (5)
H4A	0.3716	0.7266	0.5825	0.065*
C4	0.6076 (4)	0.5436 (2)	0.2091 (2)	0.0557 (7)
H4	0.7495	0.5607	0.2313	0.067*
C5	0.5096 (5)	0.4414 (2)	0.1251 (3)	0.0680 (8)
H5	0.5877	0.3882	0.0911	0.082*
C6	0.5894 (4)	0.7301 (2)	0.3589 (2)	0.0522 (6)
C7	0.8750 (3)	0.89703 (19)	0.4275 (2)	0.0458 (6)
C8	0.8041 (4)	0.9772 (2)	0.5031 (2)	0.0558 (7)
H8	0.6698	0.9625	0.5058	0.067*
C9	1.0706 (4)	0.9205 (2)	0.4249 (2)	0.0556 (6)
H9	1.1201	0.8653	0.3725	0.067*
C10	0.6170 (4)	1.0792 (2)	0.8812 (3)	0.0671 (8)
H10	0.6015	1.1572	0.9219	0.081*
C11	0.4505 (4)	0.9927 (2)	0.8333 (2)	0.0582 (7)
H11	0.3243	1.0105	0.8426	0.070*
C12	0.4690 (4)	0.8799 (2)	0.7717 (2)	0.0517 (6)
C13	0.6558 (4)	0.8578 (2)	0.7638 (3)	0.0612 (7)
H13	0.6748	0.7810	0.7224	0.073*
C14	0.8155 (4)	0.9488 (3)	0.8169 (3)	0.0712 (8)
H14	0.9447	0.9316	0.8128	0.085*
C15	0.2873 (4)	0.7842 (2)	0.7236 (3)	0.0558 (6)
H15	0.173 (6)	0.289 (3)	−0.050 (4)	0.135 (14)*
C16	0.1331 (3)	0.6052 (2)	0.5602 (2)	0.0483 (6)
H16	0.026 (6)	0.191 (4)	−0.110 (4)	0.130 (14)*
C17	−0.0548 (4)	0.5897 (2)	0.5761 (2)	0.0569 (7)
H17	−0.0939	0.6510	0.6283	0.068*
C18	0.1870 (4)	0.5146 (2)	0.4836 (2)	0.0563 (7)
H18	0.3165	0.5244	0.4720	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0723 (13)	0.0736 (12)	0.0619 (12)	−0.0209 (9)	0.0365 (11)	−0.0191 (9)
N1	0.101 (2)	0.0679 (15)	0.0548 (16)	−0.0267 (14)	0.0189 (15)	−0.0060 (12)
C1	0.070 (2)	0.091 (2)	0.0567 (19)	−0.0302 (16)	0.0055 (16)	−0.0115 (16)
O2	0.0662 (13)	0.0869 (13)	0.0788 (15)	−0.0163 (10)	0.0395 (11)	−0.0206 (10)
N2	0.0530 (12)	0.0506 (11)	0.0433 (12)	−0.0092 (9)	0.0136 (9)	−0.0091 (8)
C2	0.0580 (17)	0.0734 (17)	0.0593 (18)	−0.0111 (13)	0.0120 (14)	−0.0043 (14)
O3	0.0852 (15)	0.0810 (13)	0.0592 (13)	−0.0318 (11)	0.0332 (12)	−0.0226 (10)
N3	0.0677 (16)	0.0679 (14)	0.0659 (16)	−0.0140 (11)	0.0201 (13)	−0.0044 (12)
C3	0.0562 (16)	0.0519 (13)	0.0396 (14)	−0.0060 (11)	0.0122 (12)	0.0012 (10)
N4	0.0539 (13)	0.0534 (11)	0.0528 (13)	−0.0095 (9)	0.0181 (10)	−0.0038 (9)
C4	0.0661 (17)	0.0486 (13)	0.0466 (15)	−0.0039 (11)	0.0126 (13)	−0.0002 (11)
C5	0.094 (2)	0.0542 (15)	0.0542 (17)	−0.0023 (14)	0.0240 (16)	0.0021 (12)
C6	0.0523 (15)	0.0524 (14)	0.0472 (15)	−0.0070 (11)	0.0130 (12)	0.0000 (11)
C7	0.0471 (14)	0.0471 (12)	0.0387 (13)	−0.0033 (10)	0.0110 (11)	−0.0035 (10)
C8	0.0473 (14)	0.0605 (14)	0.0546 (16)	−0.0063 (11)	0.0176 (12)	−0.0122 (12)
C9	0.0536 (15)	0.0536 (13)	0.0558 (16)	−0.0037 (11)	0.0198 (13)	−0.0126 (11)
C10	0.071 (2)	0.0572 (15)	0.0680 (19)	−0.0055 (13)	0.0215 (16)	−0.0059 (13)
C11	0.0575 (16)	0.0543 (14)	0.0620 (17)	0.0015 (11)	0.0206 (14)	−0.0006 (12)
C12	0.0530 (16)	0.0498 (13)	0.0489 (15)	−0.0001 (10)	0.0123 (12)	0.0032 (11)
C13	0.0532 (16)	0.0585 (15)	0.0693 (19)	−0.0023 (12)	0.0219 (14)	−0.0072 (13)
C14	0.0575 (18)	0.0773 (18)	0.075 (2)	−0.0038 (14)	0.0213 (15)	−0.0022 (15)
C15	0.0544 (16)	0.0547 (14)	0.0558 (17)	−0.0018 (11)	0.0171 (13)	−0.0006 (12)
C16	0.0444 (14)	0.0488 (13)	0.0488 (15)	−0.0018 (10)	0.0121 (11)	0.0030 (11)
C17	0.0500 (15)	0.0582 (14)	0.0600 (17)	−0.0005 (11)	0.0188 (13)	−0.0058 (12)
C18	0.0470 (15)	0.0604 (15)	0.0599 (17)	−0.0030 (11)	0.0194 (13)	−0.0031 (12)

O1—C6	1.232 (3)	C5—H5	0.9500
N1—C1	1.327 (4)	C7—C8	1.372 (3)
N1—C5	1.335 (4)	C7—C9	1.380 (3)
C1—C2	1.375 (4)	C8—C9i	1.383 (3)
C1—H1	0.9500	C8—H8	0.9500
O2—C15	1.223 (3)	C9—C8i	1.383 (3)
N2—C6	1.343 (3)	C9—H9	0.9500
N2—C7	1.420 (3)	C10—C11	1.375 (3)
N2—H2A	0.8800	C10—H10	0.9500
C2—C3	1.383 (3)	C11—C12	1.377 (3)
C2—H2	0.9500	C11—H11	0.9500
O3—H15	0.94 (4)	C12—C13	1.373 (3)
O3—H16	0.87 (4)	C12—C15	1.506 (3)
N3—C10	1.327 (3)	C13—C14	1.378 (4)
N3—C14	1.333 (3)	C13—H13	0.9500
C3—C4	1.379 (3)	C14—H14	0.9500
C3—C6	1.498 (3)	C16—C17	1.375 (3)
N4—C15	1.348 (3)	C16—C18	1.387 (3)
N4—C16	1.422 (3)	C17—C18ii	1.382 (3)
N4—H4A	0.8800	C17—H17	0.9500
C4—C5	1.375 (3)	C18—C17ii	1.382 (3)
C4—H4	0.9500	C18—H18	0.9500
C1—N1—C5	116.7 (2)	C9i—C8—H8	120.2
N1—C1—C2	124.0 (3)	C7—C9—C8i	121.2 (2)
N1—C1—H1	118.0	C7—C9—H9	119.4
C2—C1—H1	118.0	C8i—C9—H9	119.4
C6—N2—C7	127.0 (2)	N3—C10—C11	123.5 (2)
C6—N2—H2A	116.5	N3—C10—H10	118.2
C7—N2—H2A	116.5	C11—C10—H10	118.2
C1—C2—C3	118.8 (3)	C10—C11—C12	119.2 (2)
C1—C2—H2	120.6	C10—C11—H11	120.4
C3—C2—H2	120.6	C12—C11—H11	120.4
H15—O3—H16	100 (3)	C13—C12—C11	118.0 (2)
C10—N3—C14	116.8 (2)	C13—C12—C15	123.2 (2)
C4—C3—C2	117.9 (2)	C11—C12—C15	118.7 (2)
C4—C3—C6	123.4 (2)	C12—C13—C14	119.0 (2)
C2—C3—C6	118.6 (2)	C12—C13—H13	120.5
C15—N4—C16	126.6 (2)	C14—C13—H13	120.5
C15—N4—H4A	116.7	N3—C14—C13	123.5 (3)
C16—N4—H4A	116.7	N3—C14—H14	118.3
C5—C4—C3	119.1 (3)	C13—C14—H14	118.3
C5—C4—H4	120.5	O2—C15—N4	124.2 (2)
C3—C4—H4	120.5	O2—C15—C12	120.4 (2)
N1—C5—C4	123.5 (3)	N4—C15—C12	115.4 (2)
N1—C5—H5	118.2	C17—C16—C18	118.9 (2)
C4—C5—H5	118.2	C17—C16—N4	123.8 (2)
O1—C6—N2	124.6 (2)	C18—C16—N4	117.3 (2)
O1—C6—C3	120.3 (2)	C16—C17—C18ii	120.2 (2)
N2—C6—C3	115.1 (2)	C16—C17—H17	119.9
C8—C7—C9	119.1 (2)	C18ii—C17—H17	119.9
C8—C7—N2	123.6 (2)	C17ii—C18—C16	120.8 (2)
C9—C7—N2	117.2 (2)	C17ii—C18—H18	119.6
C7—C8—C9i	119.6 (2)	C16—C18—H18	119.6
C7—C8—H8	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3iii	0.88	2.00	2.847 (3)	160
N4—H4A···O1	0.88	2.12	2.968 (3)	161
O3—H15···N1	0.94 (4)	1.92 (4)	2.845 (3)	168 (3)
O3—H16···N3iv	0.87 (4)	2.01 (4)	2.849 (3)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.88	2.00	2.847 (3)	160
N4—H4A⋯O1	0.88	2.12	2.968 (3)	161
O3—H15⋯N1	0.94 (4)	1.92 (4)	2.845 (3)	168 (3)
O3—H16⋯N3ii	0.87 (4)	2.01 (4)	2.849 (3)	162 (4)

Symmetry codes: (i) ; (ii) .