3-Nitro­benzaldehyde isonicotinoylhydrazone monohydrate

The crystal structure of the title compound, C₁₃H₁₂N₄O₄, contains a solvent water mol­ecule which inter­acts with the organic mol­ecules via inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.127
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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   0 ALERT level B = Potentially serious problem
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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-Nitrobenzaldehyde isonicotinoylhydrazone monohydrate

Crystal data

C13H10N4O3·H2O	F(000) = 1200
Mr = 288.27	Dx = 1.395 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3032 reflections
a = 13.374 (5) Å	θ = 2.5–26.2°
b = 13.040 (5) Å	µ = 0.11 mm^−1
c = 15.742 (6) Å	T = 294 K
V = 2745.5 (17) Å^3	Block, yellow
Z = 8	0.30 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2430 independent reflections
Radiation source: fine-focus sealed tube	1848 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.969, Tmax = 0.981	k = −15→15
13799 measured reflections	l = −11→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.4518P] where P = (Fo^2 + 2Fc^2)/3
2430 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.20 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 > 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.

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

	x	y	z	Uiso*/Ueq
O1	0.40797 (8)	0.46555 (10)	0.25113 (8)	0.0572 (4)
O2	0.18837 (10)	0.30805 (13)	0.55993 (14)	0.0866 (5)
O3	0.19816 (12)	0.27992 (16)	0.69386 (13)	0.1075 (7)
N1	0.68113 (12)	0.55279 (14)	0.04601 (10)	0.0653 (5)
N2	0.54651 (10)	0.43675 (11)	0.33008 (8)	0.0448 (4)
H2	0.6155 (15)	0.4439 (13)	0.3366 (12)	0.056 (5)*
N3	0.49113 (10)	0.40286 (11)	0.39870 (8)	0.0454 (4)
N4	0.23636 (13)	0.29636 (13)	0.62491 (14)	0.0686 (5)
C1	0.66399 (13)	0.46434 (14)	0.17829 (11)	0.0516 (4)
H1	0.6931	0.4230	0.2196	0.062*
C2	0.71817 (14)	0.49501 (17)	0.10805 (12)	0.0608 (5)
H2A	0.7844	0.4740	0.1039	0.073*
C3	0.58636 (15)	0.58293 (16)	0.05464 (13)	0.0643 (5)
H3	0.5588	0.6235	0.0121	0.077*
C4	0.52698 (13)	0.55750 (14)	0.12290 (12)	0.0549 (5)
H4	0.4616	0.5814	0.1263	0.066*
C5	0.56581 (12)	0.49594 (13)	0.18625 (10)	0.0430 (4)
C6	0.49889 (12)	0.46511 (12)	0.25825 (10)	0.0430 (4)
C7	0.54131 (11)	0.37867 (12)	0.46405 (10)	0.0451 (4)
H7	0.6106	0.3844	0.4629	0.054*
C8	0.49212 (11)	0.34204 (12)	0.54118 (10)	0.0418 (4)
C9	0.38857 (12)	0.33443 (12)	0.54605 (11)	0.0459 (4)
H9	0.3489	0.3510	0.4995	0.055*
C10	0.34606 (13)	0.30209 (13)	0.62051 (12)	0.0494 (4)
C11	0.40113 (15)	0.27592 (14)	0.69118 (12)	0.0581 (5)
H11	0.3700	0.2547	0.7410	0.070*
C12	0.50331 (14)	0.28211 (14)	0.68593 (12)	0.0594 (5)
H12	0.5424	0.2640	0.7324	0.071*
C13	0.54844 (13)	0.31524 (14)	0.61177 (12)	0.0514 (4)
H13	0.6178	0.3196	0.6092	0.062*
O4	0.75555 (10)	0.45365 (12)	0.37152 (10)	0.0645 (4)
H4A	0.8069 (18)	0.4586 (17)	0.3410 (16)	0.084 (8)*
H4B	0.7763 (17)	0.4489 (18)	0.4233 (17)	0.082 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0352 (7)	0.0870 (9)	0.0495 (7)	0.0011 (6)	−0.0023 (5)	0.0011 (7)
O2	0.0434 (8)	0.0960 (12)	0.1203 (15)	−0.0057 (7)	−0.0007 (9)	−0.0006 (10)
O3	0.0765 (11)	0.1244 (15)	0.1216 (15)	0.0031 (10)	0.0583 (11)	0.0225 (12)
N1	0.0605 (10)	0.0877 (12)	0.0478 (9)	−0.0039 (8)	0.0070 (8)	0.0068 (8)
N2	0.0338 (7)	0.0635 (9)	0.0371 (8)	−0.0004 (6)	0.0022 (6)	0.0012 (7)
N3	0.0389 (7)	0.0572 (8)	0.0402 (8)	−0.0011 (6)	0.0059 (6)	−0.0009 (6)
N4	0.0503 (10)	0.0613 (10)	0.0941 (15)	−0.0022 (8)	0.0236 (10)	0.0027 (10)
C1	0.0458 (9)	0.0726 (11)	0.0365 (9)	0.0086 (8)	0.0014 (8)	0.0009 (8)
C2	0.0471 (10)	0.0913 (14)	0.0439 (11)	0.0064 (9)	0.0051 (8)	−0.0017 (10)
C3	0.0688 (13)	0.0723 (12)	0.0518 (11)	0.0003 (10)	−0.0018 (10)	0.0164 (10)
C4	0.0466 (10)	0.0649 (11)	0.0533 (11)	0.0055 (8)	−0.0016 (8)	0.0068 (9)
C5	0.0409 (8)	0.0526 (9)	0.0356 (9)	−0.0006 (7)	−0.0025 (7)	−0.0039 (7)
C6	0.0378 (8)	0.0523 (9)	0.0388 (9)	0.0023 (7)	−0.0022 (7)	−0.0047 (7)
C7	0.0343 (8)	0.0550 (10)	0.0459 (10)	0.0010 (7)	0.0039 (7)	0.0012 (8)
C8	0.0379 (8)	0.0460 (8)	0.0415 (9)	0.0014 (6)	0.0020 (7)	−0.0012 (7)
C9	0.0411 (8)	0.0500 (9)	0.0465 (10)	0.0012 (7)	−0.0002 (7)	−0.0004 (8)
C10	0.0428 (9)	0.0466 (9)	0.0587 (11)	−0.0017 (7)	0.0110 (8)	0.0002 (8)
C11	0.0669 (12)	0.0571 (11)	0.0503 (11)	−0.0071 (9)	0.0136 (10)	0.0057 (9)
C12	0.0681 (12)	0.0638 (11)	0.0463 (11)	−0.0041 (9)	−0.0086 (9)	0.0101 (9)
C13	0.0416 (9)	0.0576 (10)	0.0549 (11)	−0.0016 (7)	−0.0035 (8)	0.0036 (9)
O4	0.0397 (7)	0.1115 (12)	0.0424 (8)	−0.0061 (7)	−0.0005 (6)	−0.0057 (7)

Geometric parameters (Å, º)

O1—C6	1.221 (2)	C4—H4	0.9300
O2—N4	1.217 (2)	C5—C6	1.499 (2)
O3—N4	1.219 (2)	C7—C8	1.461 (2)
N1—C2	1.329 (2)	C7—H7	0.9300
N1—C3	1.334 (3)	C8—C13	1.387 (2)
N2—C6	1.349 (2)	C8—C9	1.391 (2)
N2—N3	1.3823 (18)	C9—C10	1.369 (2)
N2—H2	0.933 (19)	C9—H9	0.9300
N3—C7	1.268 (2)	C10—C11	1.377 (3)
N4—C10	1.471 (3)	C11—C12	1.372 (3)
C1—C2	1.381 (2)	C11—H11	0.9300
C1—C5	1.382 (2)	C12—C13	1.383 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—H2A	0.9300	C13—H13	0.9300
C3—C4	1.377 (3)	O4—H4A	0.84 (3)
C3—H3	0.9300	O4—H4B	0.86 (3)
C4—C5	1.382 (2)
C2—N1—C3	116.50 (16)	O1—C6—C5	121.59 (15)
C6—N2—N3	119.31 (13)	N2—C6—C5	115.17 (14)
C6—N2—H2	122.2 (12)	N3—C7—C8	121.14 (14)
N3—N2—H2	118.4 (12)	N3—C7—H7	119.4
C7—N3—N2	115.46 (13)	C8—C7—H7	119.4
O2—N4—O3	123.3 (2)	C13—C8—C9	118.60 (15)
O2—N4—C10	118.69 (17)	C13—C8—C7	120.23 (14)
O3—N4—C10	118.0 (2)	C9—C8—C7	121.16 (15)
C2—C1—C5	118.99 (17)	C10—C9—C8	118.85 (16)
C2—C1—H1	120.5	C10—C9—H9	120.6
C5—C1—H1	120.5	C8—C9—H9	120.6
N1—C2—C1	123.84 (17)	C9—C10—C11	123.08 (16)
N1—C2—H2A	118.1	C9—C10—N4	118.04 (17)
C1—C2—H2A	118.1	C11—C10—N4	118.87 (17)
N1—C3—C4	123.82 (18)	C12—C11—C10	118.01 (17)
N1—C3—H3	118.1	C12—C11—H11	121.0
C4—C3—H3	118.1	C10—C11—H11	121.0
C3—C4—C5	119.12 (17)	C11—C12—C13	120.26 (17)
C3—C4—H4	120.4	C11—C12—H12	119.9
C5—C4—H4	120.4	C13—C12—H12	119.9
C4—C5—C1	117.71 (16)	C12—C13—C8	121.18 (16)
C4—C5—C6	118.50 (15)	C12—C13—H13	119.4
C1—C5—C6	123.77 (15)	C8—C13—H13	119.4
O1—C6—N2	123.24 (15)	H4A—O4—H4B	106 (2)
C6—N2—N3—C7	−179.29 (14)	N3—C7—C8—C13	179.51 (15)
C3—N1—C2—C1	1.1 (3)	N3—C7—C8—C9	−1.3 (2)
C5—C1—C2—N1	−0.9 (3)	C13—C8—C9—C10	0.8 (2)
C2—N1—C3—C4	−0.1 (3)	C7—C8—C9—C10	−178.38 (15)
N1—C3—C4—C5	−1.0 (3)	C8—C9—C10—C11	−0.4 (3)
C3—C4—C5—C1	1.1 (3)	C8—C9—C10—N4	178.90 (15)
C3—C4—C5—C6	−177.36 (17)	O2—N4—C10—C9	9.0 (3)
C2—C1—C5—C4	−0.2 (3)	O3—N4—C10—C9	−171.13 (18)
C2—C1—C5—C6	178.18 (16)	O2—N4—C10—C11	−171.70 (18)
N3—N2—C6—O1	2.4 (2)	O3—N4—C10—C11	8.2 (3)
N3—N2—C6—C5	−177.25 (13)	C9—C10—C11—C12	−0.5 (3)
C4—C5—C6—O1	22.2 (2)	N4—C10—C11—C12	−179.78 (16)
C1—C5—C6—O1	−156.24 (17)	C10—C11—C12—C13	0.9 (3)
C4—C5—C6—N2	−158.23 (15)	C11—C12—C13—C8	−0.5 (3)
C1—C5—C6—N2	23.4 (2)	C9—C8—C13—C12	−0.4 (3)
N2—N3—C7—C8	179.76 (14)	C7—C8—C13—C12	178.85 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.93 (2)	1.96 (2)	2.879 (2)	170 (2)
O4—H4A···O1^i	0.84 (3)	1.98 (3)	2.812 (2)	168 (2)
O4—H4B···N1^ii	0.86 (3)	2.01 (3)	2.876 (2)	176 (2)
C1—H1···O4	0.93	2.56	3.282 (3)	134
C7—H7···O4	0.93	2.58	3.360 (2)	142
C12—H12···O3^iii	0.93	2.39	3.221 (3)	148

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