(2E)-N,N′-Bis­(pyridin-4-yl­methyl)­but-2-enedi­amide dihydrate

In the centrosymmetric title compound, C₁₆H₁₆N₄O₂·2H₂O, the water mol­ecules donate two hydrogen bonds and accept one each, with O...O and O...N distances of 2.7498 (13) and 2.8152 (13) Å, respectively, and with an N...O distance of 2.7368 (13) Å. In the crystal structure, molecular channels are formed which are are occupied by water.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.111
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Atwood & Barbour, 2003).

(2E)-N,N'-bis(pyridin-4-ylmethyl)but-2-enediamide dihydrate

Crystal data

C16H16N4O2·2H2O	Z = 1
Mr = 332.36	F(000) = 176
Triclinic, P1	Dx = 1.314 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7867 (9) Å	Cell parameters from 4737 reflections
b = 7.0884 (9) Å	θ = 3.1–28.3°
c = 9.5620 (13) Å	µ = 0.10 mm^−1
α = 107.597 (2)°	T = 100 K
β = 101.854 (2)°	Block, colorless
γ = 97.474 (2)°	0.25 × 0.20 × 0.10 mm
V = 419.92 (10) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	1927 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997; Blessing, 1995)	h = −9→8
Tmin = 0.976, Tmax = 0.986	k = −9→9
4737 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.1309P] where P = (Fo^2 + 2Fc^2)/3
1927 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.32 e Å^−3
2 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
O10	0.78698 (13)	−0.11221 (12)	0.66236 (9)	0.0253 (2)
N8	0.69793 (14)	0.18242 (13)	0.65686 (10)	0.0179 (2)
H8	0.7301	0.2953	0.6385	0.021*
O12	0.75508 (15)	0.47846 (12)	0.53153 (9)	0.0289 (2)
C9	0.80713 (16)	0.03796 (15)	0.62281 (11)	0.0177 (2)
N3	0.65859 (19)	0.34817 (16)	1.21212 (11)	0.0315 (3)
C7	0.52742 (16)	0.15464 (16)	0.72363 (12)	0.0189 (2)
H7B	0.4626	0.0090	0.6843	0.023*
H7A	0.4236	0.2275	0.6884	0.023*
C6	0.58048 (16)	0.22513 (15)	0.89505 (12)	0.0180 (2)
C11	0.95109 (16)	0.07133 (16)	0.52956 (11)	0.0180 (2)
H11	0.9731	0.1966	0.5122	0.022*
C1	0.77998 (18)	0.29023 (18)	0.98647 (13)	0.0244 (3)
H1	0.8936	0.2941	0.9428	0.029*
C5	0.42088 (18)	0.22154 (17)	0.96569 (13)	0.0233 (3)
H5	0.2820	0.1769	0.9068	0.028*
C4	0.4665 (2)	0.28369 (18)	1.12275 (14)	0.0287 (3)
H4	0.3559	0.2804	1.1693	0.034*
C2	0.8113 (2)	0.3500 (2)	1.14362 (14)	0.0309 (3)
H2	0.9487	0.3944	1.2054	0.037*
H12B	0.7170	0.4448	0.4308	0.047 (5)*
H12A	0.7594	0.6058	0.5609	0.040 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O10	0.0354 (5)	0.0209 (4)	0.0283 (4)	0.0097 (3)	0.0194 (4)	0.0116 (3)
N8	0.0209 (4)	0.0185 (4)	0.0172 (4)	0.0050 (3)	0.0095 (3)	0.0069 (3)
O12	0.0499 (6)	0.0210 (4)	0.0198 (4)	0.0105 (4)	0.0123 (4)	0.0093 (3)
C9	0.0205 (5)	0.0180 (5)	0.0142 (5)	0.0035 (4)	0.0069 (4)	0.0034 (4)
N3	0.0509 (7)	0.0271 (5)	0.0189 (5)	0.0096 (5)	0.0134 (5)	0.0078 (4)
C7	0.0176 (5)	0.0234 (5)	0.0164 (5)	0.0045 (4)	0.0078 (4)	0.0053 (4)
C6	0.0240 (5)	0.0154 (5)	0.0170 (5)	0.0054 (4)	0.0093 (4)	0.0056 (4)
C11	0.0197 (5)	0.0193 (5)	0.0163 (5)	0.0033 (4)	0.0070 (4)	0.0067 (4)
C1	0.0250 (6)	0.0272 (6)	0.0199 (5)	0.0037 (4)	0.0076 (4)	0.0061 (4)
C5	0.0266 (6)	0.0228 (5)	0.0247 (5)	0.0071 (4)	0.0134 (4)	0.0088 (4)
C4	0.0427 (7)	0.0265 (6)	0.0260 (6)	0.0111 (5)	0.0225 (5)	0.0113 (5)
C2	0.0365 (7)	0.0316 (6)	0.0197 (6)	0.0031 (5)	0.0028 (5)	0.0063 (5)

Geometric parameters (Å, º)

O10—C9	1.2335 (13)	C7—H7A	0.9900
N8—C9	1.3412 (13)	C6—C1	1.3847 (16)
N8—C7	1.4511 (13)	C6—C5	1.3907 (15)
N8—H8	0.8800	C11—C11^i	1.329 (2)
O12—H12B	0.8914	C11—H11	0.9500
O12—H12A	0.8548	C1—C2	1.3940 (16)
C9—C11	1.4937 (14)	C1—H1	0.9500
N3—C2	1.3354 (18)	C5—C4	1.3852 (17)
N3—C4	1.3376 (19)	C5—H5	0.9500
C7—C6	1.5104 (14)	C4—H4	0.9500
C7—H7B	0.9900	C2—H2	0.9500
C9—N8—C7	120.76 (9)	C5—C6—C7	118.47 (10)
C9—N8—H8	119.6	C11^i—C11—C9	121.07 (12)
C7—N8—H8	119.6	C11^i—C11—H11	119.5
H12B—O12—H12A	102.0	C9—C11—H11	119.5
O10—C9—N8	122.77 (9)	C6—C1—C2	118.85 (11)
O10—C9—C11	122.80 (9)	C6—C1—H1	120.6
N8—C9—C11	114.41 (9)	C2—C1—H1	120.6
C2—N3—C4	117.09 (10)	C4—C5—C6	119.32 (11)
N8—C7—C6	115.96 (9)	C4—C5—H5	120.3
N8—C7—H7B	108.3	C6—C5—H5	120.3
C6—C7—H7B	108.3	N3—C4—C5	123.32 (11)
N8—C7—H7A	108.3	N3—C4—H4	118.3
C6—C7—H7A	108.3	C5—C4—H4	118.3
H7B—C7—H7A	107.4	N3—C2—C1	123.58 (12)
C1—C6—C5	117.83 (10)	N3—C2—H2	118.2
C1—C6—C7	123.69 (9)	C1—C2—H2	118.2
C7—N8—C9—O10	−9.16 (16)	C7—C6—C1—C2	−179.31 (10)
C7—N8—C9—C11	169.30 (9)	C1—C6—C5—C4	0.45 (16)
C9—N8—C7—C6	89.78 (12)	C7—C6—C5—C4	179.36 (10)
N8—C7—C6—C1	−7.65 (15)	C2—N3—C4—C5	−0.45 (18)
N8—C7—C6—C5	173.51 (9)	C6—C5—C4—N3	0.01 (18)
O10—C9—C11—C11^i	7.42 (19)	C4—N3—C2—C1	0.44 (18)
N8—C9—C11—C11^i	−171.05 (12)	C6—C1—C2—N3	0.02 (19)
C5—C6—C1—C2	−0.47 (17)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O12	0.88	1.89	2.7368 (13)	161
O12—H12A···O10^ii	0.85	1.91	2.7498 (13)	170
O12—H12B···N3^iii	0.89	1.93	2.8152 (13)	173

Symmetry codes: (ii) x, y+1, z; (iii) x, y, z−1.