N'-(3-Phenyl-allyl-idene)nicotinohydrazide monohydrate.

In the title compound, C(15)H(13)N(3)O·H(2)O, the dihedral angle between the pyridine and phenyl rings is 35.45 (7)°. Inter-molecular O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds are found in the crystal structure. In addition, C-H⋯π inter-actions involving the pyridine and phenyl rings are also found.

Related literature

For a related crystal structure and its chemical and biological applications, see: Archana et al. (2009 ▶).

Experimental

Crystal data

C15H13N3O·H2O

M = 269.30

Monoclinic,

a = 9.8456 (3) Å

b = 9.1288 (3) Å

c = 15.5389 (5) Å

β = 95.938 (3)°

V = 1389.12 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 110 K

0.48 × 0.45 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 ▶) T min = 0.704, T max = 1.000

6007 measured reflections

2742 independent reflections

2346 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.05

2742 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043001/wn2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043001/wn2355Isup2.hkl

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

C15H13N3O·H2O	F(000) = 568
Mr = 269.30	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Melting point: 463 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 9.8456 (3) Å	Cell parameters from 3706 reflections
b = 9.1288 (3) Å	θ = 4.5–74.0°
c = 15.5389 (5) Å	µ = 0.72 mm−1
β = 95.938 (3)°	T = 110 K
V = 1389.12 (8) Å3	Plate, colourless
Z = 4	0.48 × 0.45 × 0.24 mm

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer	2742 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2346 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 74.6°, θmin = 4.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→9
Tmin = 0.704, Tmax = 1.000	l = −13→18
6007 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0821P)2 + 0.2609P] where P = (Fo2 + 2Fc2)/3
2742 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O7	0.47479 (10)	0.51591 (11)	0.11459 (6)	0.0278 (3)
N1	0.16249 (12)	0.38852 (13)	−0.06770 (7)	0.0251 (3)
N8	0.40129 (11)	0.37087 (13)	0.21906 (7)	0.0229 (3)
N9	0.50761 (11)	0.41751 (13)	0.27801 (7)	0.0239 (3)
C2	0.26809 (14)	0.41542 (15)	−0.00816 (8)	0.0234 (4)
C3	0.26600 (13)	0.38761 (14)	0.08017 (8)	0.0213 (3)
C4	0.14754 (14)	0.32800 (15)	0.10770 (8)	0.0245 (4)
C5	0.03714 (14)	0.30162 (16)	0.04673 (9)	0.0266 (4)
C6	0.04847 (14)	0.33422 (15)	−0.03908 (9)	0.0249 (4)
C7	0.39013 (13)	0.43067 (15)	0.13894 (8)	0.0214 (3)
C10	0.51203 (13)	0.35650 (15)	0.35280 (9)	0.0244 (4)
C11	0.61459 (14)	0.39886 (15)	0.42168 (9)	0.0253 (4)
C12	0.61879 (13)	0.33520 (16)	0.49986 (8)	0.0252 (4)
C21	0.71252 (14)	0.36867 (15)	0.57704 (8)	0.0241 (4)
C22	0.79857 (16)	0.49073 (16)	0.58318 (9)	0.0308 (4)
C23	0.89016 (17)	0.51244 (18)	0.65604 (10)	0.0366 (5)
C24	0.89795 (15)	0.41399 (17)	0.72450 (9)	0.0319 (4)
C25	0.80997 (15)	0.29477 (17)	0.72029 (9)	0.0306 (4)
C26	0.71789 (14)	0.27272 (17)	0.64743 (9)	0.0273 (4)
O1W	0.26480 (10)	0.11005 (11)	0.26235 (6)	0.0266 (3)
H2	0.34889	0.45566	−0.02707	0.0281*
H4	0.14252	0.30588	0.16702	0.0294*
H5	−0.04511	0.26171	0.06373	0.0320*
H6	−0.02844	0.31734	−0.08004	0.0299*
H8	0.3493 (18)	0.294 (2)	0.2342 (11)	0.035 (5)*
H10	0.44733	0.28292	0.36291	0.0293*
H11	0.67948	0.47225	0.41157	0.0304*
H12	0.55372	0.26002	0.50588	0.0302*
H22	0.79430	0.55943	0.53706	0.0369*
H23	0.94833	0.59572	0.65915	0.0440*
H24	0.96260	0.42804	0.77357	0.0383*
H25	0.81272	0.22804	0.76735	0.0366*
H26	0.65768	0.19119	0.64543	0.0328*
H1W	0.335 (3)	0.054 (3)	0.2663 (14)	0.057 (6)*
H2W	0.232 (3)	0.106 (3)	0.3128 (16)	0.070 (7)*

	U11	U22	U33	U12	U13	U23
O7	0.0289 (5)	0.0327 (5)	0.0219 (5)	−0.0068 (4)	0.0028 (4)	0.0027 (4)
N1	0.0305 (6)	0.0268 (6)	0.0179 (5)	0.0013 (5)	0.0022 (4)	−0.0001 (4)
N8	0.0222 (5)	0.0268 (6)	0.0192 (6)	−0.0023 (4)	−0.0006 (4)	0.0013 (4)
N9	0.0247 (5)	0.0273 (6)	0.0191 (5)	−0.0010 (4)	−0.0004 (4)	−0.0012 (4)
C2	0.0267 (6)	0.0245 (7)	0.0194 (6)	0.0002 (5)	0.0046 (5)	0.0002 (5)
C3	0.0246 (6)	0.0204 (6)	0.0189 (6)	0.0021 (5)	0.0023 (5)	0.0008 (5)
C4	0.0263 (7)	0.0281 (7)	0.0194 (6)	0.0018 (5)	0.0032 (5)	0.0042 (5)
C5	0.0245 (6)	0.0295 (7)	0.0259 (7)	−0.0008 (5)	0.0029 (5)	0.0033 (5)
C6	0.0263 (6)	0.0242 (7)	0.0235 (7)	0.0020 (5)	−0.0007 (5)	−0.0009 (5)
C7	0.0231 (6)	0.0233 (6)	0.0182 (6)	0.0019 (5)	0.0036 (5)	−0.0004 (5)
C10	0.0249 (6)	0.0262 (7)	0.0219 (7)	0.0004 (5)	0.0014 (5)	0.0000 (5)
C11	0.0267 (7)	0.0260 (7)	0.0230 (7)	−0.0003 (5)	0.0013 (5)	−0.0019 (5)
C12	0.0241 (6)	0.0274 (7)	0.0236 (7)	−0.0002 (5)	0.0008 (5)	−0.0009 (5)
C21	0.0251 (6)	0.0268 (7)	0.0203 (6)	0.0040 (5)	0.0023 (5)	−0.0016 (5)
C22	0.0424 (8)	0.0250 (7)	0.0233 (7)	−0.0025 (6)	−0.0042 (6)	0.0028 (5)
C23	0.0461 (9)	0.0304 (8)	0.0310 (8)	−0.0089 (7)	−0.0074 (7)	−0.0004 (6)
C24	0.0352 (8)	0.0385 (8)	0.0202 (7)	0.0001 (6)	−0.0053 (6)	−0.0034 (6)
C25	0.0338 (7)	0.0383 (8)	0.0194 (6)	0.0016 (6)	0.0021 (5)	0.0044 (5)
C26	0.0263 (6)	0.0332 (7)	0.0229 (7)	−0.0011 (5)	0.0044 (5)	0.0011 (5)
O1W	0.0283 (5)	0.0294 (5)	0.0220 (5)	0.0024 (4)	0.0023 (4)	0.0048 (4)

O7—C7	1.2283 (16)	C21—C26	1.3980 (19)
O1W—H1W	0.86 (3)	C22—C23	1.387 (2)
O1W—H2W	0.88 (3)	C23—C24	1.389 (2)
N1—C2	1.3410 (17)	C24—C25	1.388 (2)
N1—C6	1.3443 (18)	C25—C26	1.390 (2)
N8—N9	1.3848 (15)	C2—H2	0.9500
N8—C7	1.3534 (17)	C4—H4	0.9500
N9—C10	1.2854 (18)	C5—H5	0.9500
N8—H8	0.914 (18)	C6—H6	0.9500
C2—C3	1.3981 (18)	C10—H10	0.9500
C3—C4	1.3938 (19)	C11—H11	0.9500
C3—C7	1.5004 (18)	C12—H12	0.9500
C4—C5	1.3871 (19)	C22—H22	0.9500
C5—C6	1.382 (2)	C23—H23	0.9500
C10—C11	1.4461 (19)	C24—H24	0.9500
C11—C12	1.3435 (19)	C25—H25	0.9500
C12—C21	1.4678 (18)	C26—H26	0.9500
C21—C22	1.397 (2)
O1W···N1i	2.9222 (15)	C22···H11	2.8000
O1W···O7ii	3.1550 (14)	C23···H5ix	2.9900
O1W···N9ii	2.9655 (15)	C24···H5ix	3.0700
O1W···C4	3.2392 (16)	C25···H5ix	2.9900
O1W···N8	2.8486 (15)	C26···H5ix	2.8000
O7···C10iii	3.1507 (17)	H1W···N9ii	2.16 (3)
O7···N9	2.6814 (14)	H1W···H8	2.26 (3)
O7···C2iv	3.2253 (17)	H1W···O7ii	2.52 (3)
O7···O1Wiii	3.1550 (14)	H1W···C10ii	3.09 (3)
O1W···H10	2.7500	H2···O7	2.4700
O1W···H8	1.944 (18)	H2···O7iv	2.3300
O1W···H4	2.5400	H2W···N1i	2.05 (3)
O7···H2	2.4700	H2W···C2i	2.78 (2)
O7···H10iii	2.5700	H2W···H8	2.46 (3)
O7···H12iii	2.9100	H4···O1W	2.5400
O7···H2iv	2.3300	H4···N8	2.6600
O7···H26v	2.6200	H4···H8	2.1900
O7···H1Wiii	2.52 (3)	H5···C21x	2.6900
N1···O1Wv	2.9222 (15)	H5···C22x	2.8000
N8···O1W	2.8486 (15)	H5···C23x	2.9900
N9···O1Wiii	2.9655 (15)	H5···C24x	3.0700
N9···O7	2.6814 (14)	H5···C25x	2.9900
N1···H2Wv	2.05 (3)	H5···C26x	2.8000
N8···H26v	2.9300	H6···H24viii	2.4800
N8···H4	2.6600	H6···H23ii	2.5400
N9···H1Wiii	2.16 (3)	H8···H1W	2.26 (3)
N9···H26v	2.8400	H8···O1W	1.944 (18)
C2···O7iv	3.2253 (17)	H8···C4	2.664 (17)
C4···O1W	3.2392 (16)	H8···H10	2.1300
C4···C24vi	3.576 (2)	H8···H2W	2.46 (3)
C5···C6vii	3.429 (2)	H8···H4	2.1900
C6···C22ii	3.575 (2)	H10···O7ii	2.5700
C6···C6vii	3.4332 (19)	H10···O1W	2.7500
C6···C23ii	3.539 (2)	H10···H8	2.1300
C6···C5vii	3.429 (2)	H10···H12	2.3700
C10···C22vi	3.594 (2)	H11···H22	2.2900
C10···O7ii	3.1507 (17)	H11···C22	2.8000
C10···C21vi	3.5874 (19)	H12···H10	2.3700
C21···C10vi	3.5874 (19)	H12···H26	2.3800
C22···C10vi	3.594 (2)	H12···O7ii	2.9100
C22···C6iii	3.575 (2)	H22···C11	2.8000
C23···C6iii	3.539 (2)	H22···H11	2.2900
C24···C4vi	3.576 (2)	H22···C6iii	2.9500
C2···H2Wv	2.78 (2)	H23···C6iii	2.8700
C4···H8	2.664 (17)	H23···H6iii	2.5400
C6···H23ii	2.8700	H24···C6xi	3.0700
C6···H22ii	2.9500	H24···H6xi	2.4800
C6···H24viii	3.0700	H26···H12	2.3800
C7···H26v	2.8500	H26···O7i	2.6200
C10···H1Wiii	3.09 (3)	H26···N8i	2.9300
C11···H22	2.8000	H26···N9i	2.8400
C21···H5ix	2.6900	H26···C7i	2.8500
C22···H5ix	2.8000
H1W—O1W—H2W	106 (2)	C21—C26—C25	121.01 (14)
C2—N1—C6	116.98 (11)	N1—C2—H2	118.00
N9—N8—C7	117.93 (11)	C3—C2—H2	118.00
N8—N9—C10	114.67 (11)	C5—C4—H4	121.00
C7—N8—H8	123.5 (11)	C3—C4—H4	121.00
N9—N8—H8	118.1 (11)	C4—C5—H5	120.00
N1—C2—C3	123.71 (12)	C6—C5—H5	120.00
C2—C3—C7	117.14 (11)	C5—C6—H6	118.00
C4—C3—C7	124.77 (11)	N1—C6—H6	118.00
C2—C3—C4	118.03 (12)	N9—C10—H10	120.00
C3—C4—C5	118.66 (12)	C11—C10—H10	120.00
C4—C5—C6	119.07 (13)	C12—C11—H11	120.00
N1—C6—C5	123.52 (13)	C10—C11—H11	120.00
N8—C7—C3	115.96 (11)	C11—C12—H12	116.00
O7—C7—C3	120.96 (11)	C21—C12—H12	116.00
O7—C7—N8	123.08 (12)	C23—C22—H22	120.00
N9—C10—C11	120.60 (12)	C21—C22—H22	120.00
C10—C11—C12	120.49 (13)	C22—C23—H23	120.00
C11—C12—C21	127.36 (13)	C24—C23—H23	120.00
C12—C21—C22	123.19 (12)	C25—C24—H24	120.00
C12—C21—C26	118.59 (12)	C23—C24—H24	120.00
C22—C21—C26	118.21 (12)	C24—C25—H25	120.00
C21—C22—C23	120.55 (13)	C26—C25—H25	120.00
C22—C23—C24	120.84 (15)	C21—C26—H26	119.00
C23—C24—C25	119.11 (14)	C25—C26—H26	119.00
C24—C25—C26	120.21 (13)
C6—N1—C2—C3	1.2 (2)	C3—C4—C5—C6	0.4 (2)
C2—N1—C6—C5	−2.0 (2)	C4—C5—C6—N1	1.2 (2)
C7—N8—N9—C10	179.89 (12)	N9—C10—C11—C12	179.83 (13)
N9—N8—C7—O7	5.25 (19)	C10—C11—C12—C21	−177.76 (13)
N9—N8—C7—C3	−174.34 (11)	C11—C12—C21—C22	10.7 (2)
N8—N9—C10—C11	−177.62 (12)	C11—C12—C21—C26	−168.23 (14)
N1—C2—C3—C4	0.3 (2)	C12—C21—C22—C23	−176.56 (14)
N1—C2—C3—C7	−177.10 (12)	C26—C21—C22—C23	2.4 (2)
C2—C3—C4—C5	−1.10 (19)	C12—C21—C26—C25	176.51 (13)
C7—C3—C4—C5	176.05 (13)	C22—C21—C26—C25	−2.5 (2)
C2—C3—C7—O7	16.54 (19)	C21—C22—C23—C24	−0.3 (2)
C2—C3—C7—N8	−163.87 (12)	C22—C23—C24—C25	−1.7 (2)
C4—C3—C7—O7	−160.64 (13)	C23—C24—C25—C26	1.6 (2)
C4—C3—C7—N8	18.96 (19)	C24—C25—C26—C21	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7ii	0.86 (3)	2.52 (3)	3.1550 (14)	131.9 (19)
O1W—H1W···N9ii	0.86 (3)	2.16 (3)	2.9655 (15)	157 (2)
O1W—H2W···N1i	0.88 (3)	2.05 (3)	2.9222 (15)	176 (2)
N8—H8···O1W	0.914 (18)	1.944 (18)	2.8486 (15)	170.3 (17)
C2—H2···O7iv	0.95	2.33	3.2253 (17)	157
C4—H4···O1W	0.95	2.54	3.2392 (16)	130
C10—H10···O7ii	0.95	2.57	3.1507 (17)	120
C22—H22···Cg1iii	0.95	2.94	3.7742 (16)	148
C5—H5···Cg2x	0.95	2.54	3.4342 (15)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7i	0.86 (3)	2.52 (3)	3.1550 (14)	131.9 (19)
O1W—H1W⋯N9i	0.86 (3)	2.16 (3)	2.9655 (15)	157 (2)
O1W—H2W⋯N1ii	0.88 (3)	2.05 (3)	2.9222 (15)	176 (2)
N8—H8⋯O1W	0.914 (18)	1.944 (18)	2.8486 (15)	170.3 (17)
C2—H2⋯O7iii	0.95	2.33	3.2253 (17)	157
C4—H4⋯O1W	0.95	2.54	3.2392 (16)	130
C10—H10⋯O7i	0.95	2.57	3.1507 (17)	120
C22—H22⋯Cg1iv	0.95	2.94	3.7742 (16)	148
C5—H5⋯Cg2v	0.95	2.54	3.4342 (15)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the N1–C6 and C21–C26 rings, respectively.