2-Nitro­benzaldehyde benzoyl­hydrazone monohydrate

The title compound, C₁₄H₁₁N₃O₃, was prepared by the reaction of 2-nitro­benzophenone and benzoyl­hydrazine. In the crystal structure, there are some inter­molecular N—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.153
• Data-to-parameter ratio = 13.4

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S1. Comment

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

The C13—N2 distance of 1.269 (4) Å is shorter than the one of 1.287 Å reported by Tucker et al. (1975). The C1—O1 distance of 1.240 (2)Å is shorter than the reported distance of 1.298Å by Sutherland & Hoy (1968). The structure of (I) is stabilized by the intermolecular N—H···O hydrogen bonds (Table 1).

Related literature

For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

S2. Experimental

A mixture of the 2-nitrylbenzophenone (0.1 mol), and benzoyl hydrazine (0.1 mol) was stirred in refluxing ethanol (30 mL) for 5 h to afford the title compound (I) (0.085 mol, yield 85%). Single crystals of (I) suitable for X-ray measurements were obtained by slow evaporation from ethanol at room temperature.

S3. Refinement

The H atom of the NH group were found from a difference Fourier map and refined freely. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

Figures

Fig. 1. The structure of the title compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2-Nitrobenzaldehyde benzoylhydrazone monohydrate

Crystal data

C14H11N3O3	Z = 4
Mr = 269.26	F(000) = 560
Monoclinic, P21/n	Dx = 1.403 Mg m^−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 6.9121 (12) Å	θ = 3.0–26.0°
b = 25.854 (2) Å	µ = 0.10 mm^−1
c = 7.6626 (14) Å	T = 113 K
β = 111.406 (7)°	Block, colourless
V = 1274.9 (3) Å^3	0.22 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2499 independent reflections
Radiation source: fine-focus sealed tube	1894 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.978, Tmax = 0.990	k = −31→30
9812 measured reflections	l = −9→8

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0874P)^2] where P = (Fo^2 + 2Fc^2)/3
2499 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.30 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
O1	0.40173 (19)	0.30647 (5)	0.67476 (18)	0.0299 (4)
O2	0.0596 (3)	0.06885 (6)	0.4061 (2)	0.0443 (4)
O3	0.2749 (3)	0.00827 (6)	0.5525 (2)	0.0509 (5)
N1	0.1914 (2)	0.24328 (6)	0.4954 (2)	0.0250 (4)
N2	0.2363 (2)	0.21033 (6)	0.6474 (2)	0.0250 (4)
N3	0.1778 (3)	0.04839 (7)	0.5520 (3)	0.0341 (5)
C1	0.2827 (3)	0.29049 (8)	0.5203 (2)	0.0233 (4)
C2	0.2344 (3)	0.32216 (7)	0.3462 (3)	0.0240 (5)
C3	0.2281 (3)	0.37602 (8)	0.3620 (3)	0.0275 (5)
H3	0.2490	0.3914	0.4802	0.033*
C4	0.1913 (3)	0.40687 (8)	0.2055 (3)	0.0325 (5)
H4	0.1845	0.4434	0.2158	0.039*
C5	0.1644 (3)	0.38448 (9)	0.0339 (3)	0.0352 (5)
H5	0.1400	0.4058	−0.0729	0.042*
C6	0.1727 (3)	0.33112 (9)	0.0163 (3)	0.0333 (5)
H6	0.1546	0.3161	−0.1017	0.040*
C7	0.2077 (3)	0.29990 (8)	0.1728 (3)	0.0269 (5)
H7	0.2135	0.2634	0.1617	0.032*
C8	0.1707 (3)	0.16388 (8)	0.6035 (3)	0.0252 (5)
H8	0.1034	0.1541	0.4760	0.030*
C9	0.2021 (3)	0.12596 (7)	0.7554 (3)	0.0235 (5)
C10	0.2048 (3)	0.07208 (8)	0.7335 (3)	0.0270 (5)
C11	0.2366 (3)	0.03809 (8)	0.8819 (3)	0.0337 (5)
H11	0.2405	0.0019	0.8629	0.040*
C12	0.2625 (3)	0.05726 (9)	1.0573 (3)	0.0381 (6)
H12	0.2814	0.0343	1.1590	0.046*
C13	0.2607 (3)	0.11027 (8)	1.0839 (3)	0.0316 (5)
H13	0.2782	0.1236	1.2043	0.038*
C14	0.2337 (3)	0.14395 (8)	0.9368 (3)	0.0257 (5)
H14	0.2367	0.1802	0.9589	0.031*
H1	0.090 (3)	0.2336 (8)	0.385 (3)	0.042 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0265 (7)	0.0331 (8)	0.0229 (8)	−0.0030 (6)	0.0004 (6)	−0.0015 (6)
O2	0.0554 (10)	0.0454 (10)	0.0318 (9)	−0.0092 (8)	0.0156 (8)	−0.0059 (7)
O3	0.0606 (11)	0.0348 (10)	0.0656 (12)	0.0028 (8)	0.0329 (10)	−0.0128 (8)
N1	0.0195 (8)	0.0317 (10)	0.0181 (9)	−0.0038 (7)	0.0002 (7)	0.0029 (7)
N2	0.0177 (7)	0.0308 (10)	0.0231 (9)	0.0001 (6)	0.0036 (6)	0.0035 (7)
N3	0.0361 (10)	0.0327 (11)	0.0392 (12)	−0.0095 (8)	0.0206 (9)	−0.0067 (8)
C1	0.0158 (8)	0.0305 (11)	0.0214 (10)	0.0022 (7)	0.0043 (7)	0.0009 (8)
C2	0.0131 (8)	0.0331 (11)	0.0234 (11)	0.0001 (7)	0.0037 (7)	0.0030 (8)
C3	0.0181 (9)	0.0313 (12)	0.0312 (11)	0.0013 (8)	0.0067 (8)	0.0016 (9)
C4	0.0201 (9)	0.0346 (12)	0.0386 (13)	0.0018 (8)	0.0058 (9)	0.0088 (9)
C5	0.0223 (10)	0.0454 (14)	0.0332 (12)	−0.0032 (9)	0.0046 (9)	0.0140 (10)
C6	0.0225 (9)	0.0499 (14)	0.0246 (11)	−0.0055 (9)	0.0051 (8)	0.0021 (10)
C7	0.0176 (9)	0.0351 (12)	0.0261 (11)	−0.0021 (8)	0.0057 (8)	−0.0016 (9)
C8	0.0180 (9)	0.0333 (12)	0.0220 (10)	−0.0008 (8)	0.0047 (8)	−0.0002 (9)
C9	0.0136 (8)	0.0290 (11)	0.0262 (11)	−0.0003 (7)	0.0052 (7)	0.0012 (8)
C10	0.0223 (9)	0.0315 (11)	0.0292 (11)	−0.0021 (8)	0.0116 (8)	−0.0026 (9)
C11	0.0333 (11)	0.0300 (12)	0.0393 (13)	0.0040 (9)	0.0151 (10)	0.0061 (10)
C12	0.0359 (12)	0.0434 (14)	0.0345 (13)	0.0040 (10)	0.0123 (10)	0.0119 (10)
C13	0.0262 (10)	0.0412 (13)	0.0251 (11)	0.0005 (9)	0.0066 (9)	0.0024 (9)
C14	0.0164 (8)	0.0312 (11)	0.0265 (11)	0.0002 (7)	0.0043 (8)	0.0012 (8)

Geometric parameters (Å, º)

O1—C1	1.240 (2)	C5—H5	0.9500
O2—N3	1.237 (2)	C6—C7	1.391 (3)
O3—N3	1.235 (2)	C6—H6	0.9500
N1—C1	1.355 (2)	C7—H7	0.9500
N1—N2	1.384 (2)	C8—C9	1.476 (3)
N1—H1	0.92 (2)	C8—H8	0.9500
N2—C8	1.284 (2)	C9—C10	1.404 (3)
N3—C10	1.468 (3)	C9—C14	1.405 (3)
C1—C2	1.496 (3)	C10—C11	1.390 (3)
C2—C7	1.397 (3)	C11—C12	1.381 (3)
C2—C3	1.400 (3)	C11—H11	0.9500
C3—C4	1.384 (3)	C12—C13	1.386 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.386 (3)	C13—C14	1.382 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.389 (3)	C14—H14	0.9500
C1—N1—N2	119.09 (15)	C6—C7—C2	120.10 (19)
C1—N1—H1	122.3 (14)	C6—C7—H7	120.0
N2—N1—H1	118.3 (14)	C2—C7—H7	120.0
C8—N2—N1	113.94 (16)	N2—C8—C9	118.56 (17)
O3—N3—O2	122.77 (18)	N2—C8—H8	120.7
O3—N3—C10	117.79 (18)	C9—C8—H8	120.7
O2—N3—C10	119.44 (17)	C10—C9—C14	116.27 (17)
O1—C1—N1	123.17 (17)	C10—C9—C8	124.70 (18)
O1—C1—C2	121.55 (17)	C14—C9—C8	119.02 (18)
N1—C1—C2	115.26 (15)	C11—C10—C9	122.33 (19)
C7—C2—C3	119.67 (18)	C11—C10—N3	116.04 (18)
C7—C2—C1	122.13 (17)	C9—C10—N3	121.62 (17)
C3—C2—C1	118.10 (17)	C12—C11—C10	119.7 (2)
C4—C3—C2	120.0 (2)	C12—C11—H11	120.2
C4—C3—H3	120.0	C10—C11—H11	120.2
C2—C3—H3	120.0	C11—C12—C13	119.5 (2)
C3—C4—C5	120.0 (2)	C11—C12—H12	120.2
C3—C4—H4	120.0	C13—C12—H12	120.2
C5—C4—H4	120.0	C14—C13—C12	120.6 (2)
C4—C5—C6	120.70 (19)	C14—C13—H13	119.7
C4—C5—H5	119.6	C12—C13—H13	119.7
C6—C5—H5	119.6	C13—C14—C9	121.61 (19)
C5—C6—C7	119.5 (2)	C13—C14—H14	119.2
C5—C6—H6	120.2	C9—C14—H14	119.2
C7—C6—H6	120.2
C1—N1—N2—C8	−168.80 (16)	N2—C8—C9—C14	21.7 (2)
N2—N1—C1—O1	−1.9 (3)	C14—C9—C10—C11	0.1 (3)
N2—N1—C1—C2	176.60 (15)	C8—C9—C10—C11	179.52 (17)
O1—C1—C2—C7	143.21 (18)	C14—C9—C10—N3	−178.78 (16)
N1—C1—C2—C7	−35.3 (2)	C8—C9—C10—N3	0.7 (3)
O1—C1—C2—C3	−33.1 (2)	O3—N3—C10—C11	−33.6 (2)
N1—C1—C2—C3	148.40 (17)	O2—N3—C10—C11	146.05 (17)
C7—C2—C3—C4	1.3 (3)	O3—N3—C10—C9	145.36 (18)
C1—C2—C3—C4	177.71 (15)	O2—N3—C10—C9	−35.0 (3)
C2—C3—C4—C5	−1.1 (3)	C9—C10—C11—C12	1.4 (3)
C3—C4—C5—C6	0.4 (3)	N3—C10—C11—C12	−179.72 (17)
C4—C5—C6—C7	0.2 (3)	C10—C11—C12—C13	−1.3 (3)
C5—C6—C7—C2	0.0 (3)	C11—C12—C13—C14	−0.1 (3)
C3—C2—C7—C6	−0.7 (3)	C12—C13—C14—C9	1.6 (3)
C1—C2—C7—C6	−176.98 (16)	C10—C9—C14—C13	−1.6 (3)
N1—N2—C8—C9	−177.42 (14)	C8—C9—C14—C13	178.96 (16)
N2—C8—C9—C10	−157.67 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.92 (2)	1.96 (2)	2.848 (2)	163.8 (19)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.