2-[(E)-(1H-Pyrrol-2-ylmethyl-idene)hydrazinyl]pyridine monohydrate.

The title hydrate, C(10)H(10)N(4)·H(2)O, shows a small twist in the hydro-zone derivative, the dihedral angle between the pyridine and pyrrole rings being 11.08 (12)°. The pyridine and pyrrole N atoms lie to the same side of the mol-ecule being sustained in place by hydrogen-bonding inter-actions with the water mol-ecule. Further inter-molecular O-H⋯N and N-H⋯O hydrogen bonding leads to the formation of supra-molecular arrays in the ab plane.

Related literature

For related structures of hydro­zone derivatives, see: Baddeley et al. (2009 ▶); Ferguson et al. (2005 ▶); Wardell, Low & Glidewell (2007 ▶); Wardell, Skakle, Low & Glidewell (2007 ▶). For additional structural analaysis, see: Spek (2003 ▶).

Experimental

Crystal data

C10H10N4·H2O

M = 204.24

Monoclinic,

a = 5.6479 (3) Å

b = 7.4383 (4) Å

c = 24.4233 (11) Å

β = 103.300 (3)°

V = 998.52 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.24 × 0.22 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.670, T max = 0.746

3068 measured reflections

1680 independent reflections

1636 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.07

1680 reflections

149 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT data reduction: DENZO nd COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050296/hg2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050296/hg2608Isup2.hkl

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

C10H10N4·H2O	F(000) = 432
Mr = 204.24	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18744 reflections
a = 5.6479 (3) Å	θ = 2.9–27.5°
b = 7.4383 (4) Å	µ = 0.09 mm−1
c = 24.4233 (11) Å	T = 120 K
β = 103.300 (3)°	Block, colourless
V = 998.52 (9) Å3	0.24 × 0.22 × 0.04 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	1680 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1636 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.027
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.2°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −8→8
Tmin = 0.670, Tmax = 0.746	l = −28→28
3068 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.3833P] where P = (Fo2 + 2Fc2)/3
1680 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.19 e Å−3
4 restraints	Δρmin = −0.24 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 > 2σ(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
O1W	0.0268 (3)	0.5726 (2)	0.74096 (6)	0.0234 (4)
H1W	0.088 (5)	0.635 (3)	0.7695 (7)	0.035*
H2W	−0.071 (4)	0.501 (3)	0.7507 (11)	0.035*
N1	0.2897 (3)	0.7646 (2)	0.83791 (7)	0.0221 (4)
N2	0.5539 (4)	0.8844 (2)	0.78669 (8)	0.0218 (4)
H2N	0.694 (3)	0.935 (3)	0.7844 (10)	0.026*
N3	0.3760 (4)	0.8612 (2)	0.73892 (7)	0.0205 (4)
N4	0.0207 (4)	0.7784 (2)	0.64316 (7)	0.0205 (4)
H4N	0.000 (5)	0.726 (3)	0.6740 (6)	0.025*
C1	0.4955 (4)	0.8541 (3)	0.83784 (8)	0.0193 (4)
C2	0.2360 (4)	0.7344 (3)	0.88823 (8)	0.0238 (5)
H2	0.0904	0.6710	0.8886	0.029*
C3	0.3790 (5)	0.7898 (3)	0.93898 (9)	0.0257 (5)
H3	0.3346	0.7654	0.9735	0.031*
C4	0.5912 (5)	0.8829 (3)	0.93755 (9)	0.0250 (5)
H4	0.6942	0.9245	0.9716	0.030*
C5	0.6526 (4)	0.9152 (3)	0.88711 (9)	0.0229 (5)
H5	0.7981	0.9774	0.8858	0.027*
C6	0.4278 (4)	0.8846 (3)	0.69071 (8)	0.0204 (5)
H6	0.5870	0.9191	0.6882	0.024*
C7	0.2393 (4)	0.8574 (3)	0.64086 (8)	0.0196 (5)
C8	−0.1198 (4)	0.7629 (3)	0.59024 (8)	0.0230 (5)
H8	−0.2775	0.7109	0.5804	0.028*
C9	0.0049 (4)	0.8353 (3)	0.55333 (8)	0.0240 (5)
H9	−0.0522	0.8433	0.5137	0.029*
C10	0.2326 (5)	0.8955 (3)	0.58482 (8)	0.0218 (5)
H10	0.3571	0.9512	0.5705	0.026*

	U11	U22	U33	U12	U13	U23
O1W	0.0245 (9)	0.0239 (7)	0.0224 (7)	−0.0061 (6)	0.0065 (7)	0.0001 (6)
N1	0.0242 (10)	0.0196 (9)	0.0231 (9)	−0.0003 (8)	0.0066 (8)	0.0013 (7)
N2	0.0194 (10)	0.0269 (10)	0.0200 (8)	−0.0038 (8)	0.0060 (8)	0.0001 (7)
N3	0.0214 (9)	0.0194 (8)	0.0199 (8)	−0.0005 (7)	0.0027 (8)	0.0005 (7)
N4	0.0229 (10)	0.0191 (8)	0.0200 (8)	−0.0011 (8)	0.0062 (7)	0.0014 (7)
C1	0.0202 (11)	0.0159 (9)	0.0217 (10)	0.0028 (9)	0.0048 (9)	0.0013 (8)
C2	0.0269 (12)	0.0195 (9)	0.0278 (10)	0.0027 (9)	0.0120 (10)	0.0032 (9)
C3	0.0361 (13)	0.0211 (10)	0.0215 (9)	0.0040 (10)	0.0102 (10)	0.0029 (9)
C4	0.0335 (13)	0.0191 (10)	0.0198 (10)	0.0034 (10)	0.0007 (10)	−0.0001 (9)
C5	0.0251 (13)	0.0178 (9)	0.0241 (10)	0.0005 (9)	0.0025 (10)	0.0003 (8)
C6	0.0209 (11)	0.0176 (10)	0.0241 (9)	−0.0001 (8)	0.0080 (10)	−0.0016 (8)
C7	0.0221 (12)	0.0166 (9)	0.0210 (10)	0.0006 (9)	0.0069 (9)	0.0005 (8)
C8	0.0226 (12)	0.0209 (10)	0.0243 (9)	−0.0008 (9)	0.0027 (9)	−0.0020 (8)
C9	0.0301 (13)	0.0219 (10)	0.0179 (9)	0.0025 (9)	0.0013 (9)	0.0005 (9)
C10	0.0243 (12)	0.0188 (10)	0.0234 (10)	−0.0005 (9)	0.0080 (9)	−0.0008 (8)

O1W—H1W	0.842 (10)	C3—C4	1.392 (4)
O1W—H2W	0.840 (10)	C3—H3	0.9500
N1—C1	1.340 (3)	C4—C5	1.375 (3)
N1—C2	1.350 (3)	C4—H4	0.9500
N2—N3	1.364 (3)	C5—H5	0.9500
N2—C1	1.382 (3)	C6—C7	1.435 (3)
N2—H2N	0.886 (10)	C6—H6	0.9500
N3—C6	1.289 (3)	C7—C10	1.390 (3)
N4—C8	1.357 (3)	C8—C9	1.375 (3)
N4—C7	1.380 (3)	C8—H8	0.9500
N4—H4N	0.879 (10)	C9—C10	1.411 (3)
C1—C5	1.396 (3)	C9—H9	0.9500
C2—C3	1.377 (3)	C10—H10	0.9500
C2—H2	0.9500
H1W—O1W—H2W	107 (2)	C3—C4—H4	119.8
C1—N1—C2	117.39 (19)	C4—C5—C1	118.3 (2)
N3—N2—C1	118.06 (17)	C4—C5—H5	120.9
N3—N2—H2N	119.3 (16)	C1—C5—H5	120.9
C1—N2—H2N	121.9 (16)	N3—C6—C7	118.4 (2)
C6—N3—N2	119.13 (18)	N3—C6—H6	120.8
C8—N4—C7	109.25 (17)	C7—C6—H6	120.8
C8—N4—H4N	127.9 (16)	N4—C7—C10	107.7 (2)
C7—N4—H4N	121.4 (17)	N4—C7—C6	121.43 (19)
N1—C1—N2	118.01 (18)	C10—C7—C6	130.8 (2)
N1—C1—C5	122.68 (19)	N4—C8—C9	108.4 (2)
N2—C1—C5	119.31 (19)	N4—C8—H8	125.8
N1—C2—C3	124.2 (2)	C9—C8—H8	125.8
N1—C2—H2	117.9	C8—C9—C10	107.86 (18)
C3—C2—H2	117.9	C8—C9—H9	126.1
C2—C3—C4	117.1 (2)	C10—C9—H9	126.1
C2—C3—H3	121.4	C7—C10—C9	106.7 (2)
C4—C3—H3	121.4	C7—C10—H10	126.6
C5—C4—C3	120.3 (2)	C9—C10—H10	126.6
C5—C4—H4	119.8
C1—N2—N3—C6	−178.42 (18)	N2—N3—C6—C7	179.22 (17)
C2—N1—C1—N2	179.37 (18)	C8—N4—C7—C10	1.2 (2)
C2—N1—C1—C5	0.2 (3)	C8—N4—C7—C6	−177.71 (19)
N3—N2—C1—N1	15.4 (3)	N3—C6—C7—N4	−11.2 (3)
N3—N2—C1—C5	−165.42 (17)	N3—C6—C7—C10	170.2 (2)
C1—N1—C2—C3	0.0 (3)	C7—N4—C8—C9	−1.2 (2)
N1—C2—C3—C4	0.2 (3)	N4—C8—C9—C10	0.8 (2)
C2—C3—C4—C5	−0.6 (3)	N4—C7—C10—C9	−0.6 (2)
C3—C4—C5—C1	0.8 (3)	C6—C7—C10—C9	178.1 (2)
N1—C1—C5—C4	−0.6 (3)	C8—C9—C10—C7	−0.1 (2)
N2—C1—C5—C4	−179.75 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1	0.842 (10)	2.037 (11)	2.870 (2)	170 (3)
O1w—H2w···N3i	0.840 (10)	2.078 (12)	2.899 (3)	166 (3)
N2—H2n···O1wii	0.886 (10)	2.092 (12)	2.959 (3)	166 (2)
N4—H4n···O1w	0.879 (10)	1.971 (11)	2.831 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N1	0.84 (1)	2.04 (1)	2.870 (2)	170 (3)
O1w—H2w⋯N3i	0.84 (1)	2.08 (1)	2.899 (3)	166 (3)
N2—H2n⋯O1wii	0.89 (1)	2.09 (1)	2.959 (3)	166 (2)
N4—H4n⋯O1w	0.88 (1)	1.97 (1)	2.831 (2)	165 (2)

Symmetry codes: (i) ; (ii) .