(E)-N′-[4-(Di­methyl­amino)­benzyl­idene]propiono­hydrazide monohydrate

In the title hydrated hydrazine compound, C₁₂H₁₇N₃O·H₂O, the C=N bond adopts an E conformation. In the crystal, water mol­ecules bridge the hydrazine mol­ecules, via N—H...O and O—H...O hydrogen bonds, forming sheets parallel to the bc plane. There are C—H...π inter­actions present within the sheets, and further C—H...π inter­actions link the sheets to form a three-dimensional structure.

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

(E)-N'-[4-(Dimethylamino)benzylidene]propionohydrazide monohydrate

Crystal data

C12H17N3O·H2O	F(000) = 512
Mr = 237.30	Dx = 1.217 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2072 reflections
a = 12.5756 (7) Å	θ = 3.8–63.7°
b = 10.5214 (6) Å	µ = 0.69 mm^−1
c = 10.5737 (6) Å	T = 296 K
β = 112.279 (3)°	Block, colourless
V = 1294.60 (13) Å^3	0.29 × 0.26 × 0.22 mm
Z = 4

Data collection

Bruker X8 Proteum diffractometer	2072 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1799 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.053
Detector resolution: 18.4 pixels mm^-1	θmax = 63.7°, θmin = 3.8°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→11
Tmin = 0.826, Tmax = 0.864	l = −11→12
10783 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0887P)^2 + 0.250P] where P = (Fo^2 + 2Fc^2)/3
2072 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.21 e Å^−3
3 restraints	Δρmin = −0.24 e Å^−3

Special details

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 esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.01204 (10)	0.62894 (12)	0.61531 (12)	0.0317 (4)
N1	0.66806 (12)	0.86484 (13)	0.57578 (14)	0.0262 (4)
N2	0.20753 (11)	0.76812 (13)	0.69793 (13)	0.0223 (4)
N3	0.12447 (11)	0.78061 (13)	0.75446 (13)	0.0223 (4)
C1	0.67145 (15)	0.78096 (18)	0.46817 (17)	0.0300 (5)
C2	0.74862 (15)	0.97087 (16)	0.61820 (18)	0.0276 (5)
C3	0.57562 (14)	0.86170 (15)	0.61455 (15)	0.0214 (5)
C4	0.49094 (14)	0.76498 (15)	0.56646 (15)	0.0218 (5)
C5	0.39942 (13)	0.75970 (15)	0.60754 (15)	0.0213 (5)
C6	0.38583 (14)	0.85007 (15)	0.69790 (15)	0.0215 (5)
C7	0.46896 (14)	0.94588 (15)	0.74484 (16)	0.0229 (5)
C8	0.56171 (14)	0.95285 (15)	0.70483 (16)	0.0232 (5)
C9	0.29009 (14)	0.84864 (15)	0.74319 (15)	0.0222 (5)
C10	0.03017 (14)	0.70707 (15)	0.70870 (16)	0.0235 (5)
C11	−0.05031 (14)	0.72381 (16)	0.78285 (17)	0.0261 (5)
C12	−0.03320 (16)	0.61625 (18)	0.88521 (18)	0.0314 (6)
O2	0.16326 (10)	0.94926 (11)	0.97640 (12)	0.0275 (4)
H1	0.67440	0.69420	0.49750	0.0450*
H2	0.04330	0.62020	0.95350	0.0470*
H3	0.80850	0.95850	0.58410	0.0410*
H4	0.49740	0.70410	0.50610	0.0260*
H5	0.34550	0.69500	0.57480	0.0260*
H6	0.61510	1.01800	0.73770	0.0280*
H7	0.46170	1.00680	0.80480	0.0270*
H8	0.13350	0.83510	0.81830	0.0270*
H9	−0.03550	0.80470	0.83030	0.0310*
H10	−0.12920	0.72380	0.71760	0.0310*
H11	−0.04420	0.53610	0.83860	0.0470*
H12	−0.08790	0.62460	0.92800	0.0470*
H13	0.28860	0.90830	0.80740	0.0270*
H14	0.60380	0.79370	0.38730	0.0450*
H15	0.73840	0.79950	0.44860	0.0450*
H16	0.70880	1.04870	0.58230	0.0410*
H17	0.78160	0.97520	0.71620	0.0410*
H18	0.1452 (18)	0.9041 (17)	1.0300 (19)	0.0410*
H19	0.1159 (16)	1.0074 (15)	0.955 (2)	0.0410*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0339 (7)	0.0360 (7)	0.0292 (7)	−0.0111 (5)	0.0165 (5)	−0.0072 (5)
N1	0.0251 (7)	0.0296 (8)	0.0265 (8)	−0.0065 (6)	0.0126 (6)	−0.0058 (6)
N2	0.0233 (7)	0.0256 (7)	0.0212 (7)	0.0004 (5)	0.0120 (6)	0.0020 (5)
N3	0.0242 (7)	0.0253 (7)	0.0206 (7)	−0.0012 (5)	0.0120 (6)	−0.0019 (5)
C1	0.0277 (9)	0.0365 (10)	0.0292 (9)	−0.0041 (7)	0.0145 (7)	−0.0067 (7)
C2	0.0262 (9)	0.0271 (9)	0.0309 (9)	−0.0042 (7)	0.0125 (7)	0.0007 (7)
C3	0.0223 (8)	0.0228 (8)	0.0177 (8)	−0.0001 (6)	0.0061 (6)	0.0033 (6)
C4	0.0259 (9)	0.0204 (8)	0.0178 (8)	−0.0005 (6)	0.0068 (6)	−0.0007 (6)
C5	0.0218 (8)	0.0211 (8)	0.0192 (8)	−0.0027 (6)	0.0056 (6)	0.0018 (6)
C6	0.0231 (8)	0.0221 (8)	0.0184 (8)	0.0007 (6)	0.0069 (6)	0.0049 (6)
C7	0.0281 (9)	0.0209 (8)	0.0202 (8)	−0.0009 (6)	0.0098 (6)	−0.0012 (6)
C8	0.0252 (8)	0.0208 (8)	0.0226 (8)	−0.0042 (6)	0.0078 (6)	−0.0011 (6)
C9	0.0264 (9)	0.0217 (8)	0.0183 (8)	0.0012 (6)	0.0081 (6)	0.0020 (6)
C10	0.0254 (9)	0.0235 (8)	0.0227 (8)	0.0012 (6)	0.0104 (7)	0.0045 (6)
C11	0.0228 (9)	0.0281 (9)	0.0284 (9)	0.0024 (7)	0.0109 (7)	0.0015 (7)
C12	0.0354 (10)	0.0341 (10)	0.0323 (10)	0.0016 (8)	0.0216 (8)	0.0028 (7)
O2	0.0310 (7)	0.0269 (7)	0.0278 (7)	0.0054 (5)	0.0148 (5)	0.0026 (5)

Geometric parameters (Å, º)

O1—C10	1.238 (2)	C11—C12	1.524 (2)
O2—H18	0.83 (2)	C1—H1	0.9600
O2—H19	0.823 (18)	C1—H15	0.9600
N1—C1	1.453 (2)	C1—H14	0.9600
N1—C3	1.372 (2)	C2—H16	0.9600
N1—C2	1.459 (2)	C2—H17	0.9600
N2—N3	1.393 (2)	C2—H3	0.9600
N2—C9	1.284 (2)	C4—H4	0.9300
N3—C10	1.343 (2)	C5—H5	0.9300
N3—H8	0.8600	C7—H7	0.9300
C3—C4	1.420 (2)	C8—H6	0.9300
C3—C8	1.410 (2)	C9—H13	0.9300
C4—C5	1.377 (3)	C11—H10	0.9700
C5—C6	1.404 (2)	C11—H9	0.9700
C6—C7	1.401 (2)	C12—H12	0.9600
C6—C9	1.455 (3)	C12—H2	0.9600
C7—C8	1.385 (3)	C12—H11	0.9600
C10—C11	1.507 (3)
H18—O2—H19	105 (2)	N1—C1—H15	109.00
C1—N1—C2	118.82 (15)	N1—C2—H3	109.00
C1—N1—C3	119.94 (14)	N1—C2—H16	109.00
C2—N1—C3	119.67 (14)	H3—C2—H16	109.00
N3—N2—C9	114.20 (13)	H3—C2—H17	109.00
N2—N3—C10	119.64 (13)	N1—C2—H17	109.00
N2—N3—H8	120.00	H16—C2—H17	109.00
C10—N3—H8	120.00	C5—C4—H4	119.00
C4—C3—C8	117.45 (16)	C3—C4—H4	119.00
N1—C3—C8	121.51 (15)	C4—C5—H5	119.00
N1—C3—C4	121.03 (14)	C6—C5—H5	119.00
C3—C4—C5	121.26 (15)	C6—C7—H7	119.00
C4—C5—C6	121.30 (15)	C8—C7—H7	119.00
C7—C6—C9	119.37 (14)	C7—C8—H6	120.00
C5—C6—C9	123.14 (15)	C3—C8—H6	120.00
C5—C6—C7	117.49 (16)	C6—C9—H13	119.00
C6—C7—C8	122.11 (15)	N2—C9—H13	119.00
C3—C8—C7	120.38 (15)	C10—C11—H9	110.00
N2—C9—C6	122.51 (14)	C12—C11—H9	110.00
O1—C10—N3	122.71 (17)	C12—C11—H10	110.00
N3—C10—C11	114.87 (14)	C10—C11—H10	110.00
O1—C10—C11	122.39 (16)	H9—C11—H10	108.00
C10—C11—C12	109.93 (15)	C11—C12—H11	109.00
N1—C1—H1	109.00	C11—C12—H12	109.00
N1—C1—H14	109.00	C11—C12—H2	109.00
H1—C1—H14	109.00	H2—C12—H12	110.00
H1—C1—H15	109.00	H11—C12—H12	109.00
H14—C1—H15	109.00	H2—C12—H11	109.00
C1—N1—C3—C4	9.6 (2)	C4—C3—C8—C7	0.6 (2)
C1—N1—C3—C8	−171.26 (15)	C3—C4—C5—C6	0.4 (2)
C2—N1—C3—C4	175.19 (14)	C4—C5—C6—C7	0.0 (2)
C2—N1—C3—C8	−5.7 (2)	C4—C5—C6—C9	179.55 (15)
C9—N2—N3—C10	175.73 (14)	C5—C6—C7—C8	0.0 (2)
N3—N2—C9—C6	179.26 (13)	C9—C6—C7—C8	−179.60 (15)
N2—N3—C10—O1	−1.4 (2)	C5—C6—C9—N2	−3.8 (2)
N2—N3—C10—C11	176.70 (13)	C7—C6—C9—N2	175.81 (15)
N1—C3—C4—C5	178.48 (15)	C6—C7—C8—C3	−0.3 (2)
C8—C3—C4—C5	−0.7 (2)	O1—C10—C11—C12	77.2 (2)
N1—C3—C8—C7	−178.52 (15)	N3—C10—C11—C12	−100.88 (17)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H8···O2	0.86	1.98	2.8330 (18)	175
O2—H18···O1^i	0.83 (2)	2.21 (2)	2.9272 (18)	144 (2)
O2—H18···N2^i	0.83 (2)	2.45 (2)	3.1684 (18)	145 (2)
O2—H19···O1^ii	0.82 (3)	1.97 (2)	2.7845 (18)	172 (2)
C1—H14···Cg1^iii	0.96	2.83	3.567 (2)	135
C2—H16···Cg1^iv	0.96	2.91	3.701 (2)	140

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+2, −z+1.