Acetone (2-nitro­phen­yl)hydrazone

The title compound, C₉H₁₁N₃O₂, was prepared by the reaction of 1-(2-nitro­phen­yl)hydrazine with acetone at room temperature. The mol­ecule is approximately planar and exhibits a weak intra­molecular hydrogen-bond inter­action.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.160
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C8     ..  N2      ..      91.90 Deg.

   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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Acetone (2-nitrophenyl)hydrazone

Crystal data

C9H11N3O2	F(000) = 408
Mr = 193.21	Dx = 1.300 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.5080 (17) Å	θ = 4–14°
b = 15.479 (3) Å	µ = 0.10 mm^−1
c = 8.1420 (16) Å	T = 295 K
β = 112.96 (3)°	Block, red
V = 987.3 (4) Å^3	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.6°
Graphite monochromator	h = −9→10
ω scans	k = −18→0
2257 measured reflections	l = −9→0
2111 independent reflections	3 standard reflections every 100 reflections
1244 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0857P)^2 + 0.0868P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2111 reflections	Δρmax = 0.18 e Å^−3
130 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (5)

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	0.3849 (2)	0.17799 (11)	0.1594 (2)	0.0889 (5)
O2	0.5530 (2)	0.09039 (12)	0.3575 (2)	0.0881 (5)
N1	0.5059 (2)	0.12668 (11)	0.2101 (2)	0.0681 (5)
N2	0.76540 (19)	−0.00839 (11)	0.2807 (2)	0.0640 (5)
H2A	0.7268	0.0022	0.3618	0.077*
N3	0.8774 (2)	−0.07660 (11)	0.3015 (2)	0.0657 (5)
C1	0.5935 (2)	0.10844 (12)	0.0931 (2)	0.0583 (5)
C2	0.5482 (2)	0.15828 (13)	−0.0621 (3)	0.0671 (6)
H2B	0.4665	0.2015	−0.0847	0.081*
C3	0.6228 (3)	0.14391 (15)	−0.1803 (3)	0.0729 (6)
H3B	0.5941	0.1778	−0.2823	0.088*
C4	0.7420 (3)	0.07826 (15)	−0.1468 (3)	0.0739 (6)
H4A	0.7921	0.0681	−0.2281	0.089*
C5	0.7879 (3)	0.02790 (14)	0.0032 (3)	0.0661 (5)
H5A	0.8673	−0.0161	0.0209	0.079*
C6	0.7166 (2)	0.04180 (12)	0.1314 (2)	0.0559 (5)
C7	0.9043 (2)	−0.12657 (13)	0.4352 (3)	0.0643 (5)
C8	0.8259 (3)	−0.11777 (17)	0.5698 (3)	0.0849 (7)
H8A	0.7070	−0.1038	0.5102	0.127*
H8B	0.8827	−0.0726	0.6524	0.127*
H8C	0.8376	−0.1712	0.6332	0.127*
C9	1.0256 (3)	−0.20019 (16)	0.4600 (3)	0.0865 (7)
H9A	1.0654	−0.2003	0.3646	0.130*
H9B	0.9683	−0.2537	0.4593	0.130*
H9C	1.1211	−0.1938	0.5718	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0780 (10)	0.0906 (11)	0.1087 (13)	0.0138 (9)	0.0479 (9)	−0.0032 (9)
O2	0.0876 (11)	0.1120 (13)	0.0803 (11)	0.0146 (9)	0.0497 (9)	0.0049 (9)
N1	0.0586 (10)	0.0744 (11)	0.0765 (12)	−0.0061 (9)	0.0321 (9)	−0.0120 (9)
N2	0.0599 (9)	0.0751 (11)	0.0638 (10)	0.0031 (8)	0.0314 (8)	0.0010 (8)
N3	0.0590 (9)	0.0732 (11)	0.0683 (10)	0.0007 (8)	0.0284 (8)	−0.0025 (9)
C1	0.0505 (10)	0.0649 (12)	0.0602 (11)	−0.0102 (9)	0.0223 (9)	−0.0116 (9)
C2	0.0594 (11)	0.0668 (13)	0.0701 (13)	−0.0039 (9)	0.0196 (10)	−0.0054 (10)
C3	0.0793 (13)	0.0765 (13)	0.0623 (12)	−0.0057 (11)	0.0269 (11)	0.0002 (10)
C4	0.0816 (14)	0.0823 (15)	0.0687 (13)	−0.0067 (12)	0.0411 (11)	−0.0065 (11)
C5	0.0628 (11)	0.0743 (13)	0.0681 (12)	−0.0033 (10)	0.0332 (9)	−0.0062 (10)
C6	0.0469 (9)	0.0626 (11)	0.0581 (11)	−0.0115 (8)	0.0204 (8)	−0.0075 (9)
C7	0.0560 (11)	0.0727 (13)	0.0621 (11)	−0.0080 (9)	0.0207 (9)	−0.0041 (10)
C8	0.0821 (15)	0.1036 (19)	0.0744 (14)	0.0074 (13)	0.0364 (12)	0.0127 (13)
C9	0.0852 (15)	0.0823 (15)	0.0904 (16)	0.0096 (13)	0.0325 (13)	0.0020 (13)

Geometric parameters (Å, º)

O1—N1	1.237 (2)	C4—C5	1.371 (3)
O2—N1	1.241 (2)	C4—H4A	0.9300
N1—C1	1.448 (2)	C5—C6	1.414 (3)
N2—C6	1.363 (2)	C5—H5A	0.9300
N2—N3	1.388 (2)	C7—C8	1.495 (3)
N2—H2A	0.8600	C7—C9	1.497 (3)
N3—C7	1.281 (2)	C8—H8A	0.9600
C1—C2	1.401 (3)	C8—H8B	0.9600
C1—C6	1.416 (3)	C8—H8C	0.9600
C2—C3	1.362 (3)	C9—H9A	0.9600
C2—H2B	0.9300	C9—H9B	0.9600
C3—C4	1.385 (3)	C9—H9C	0.9600
C3—H3B	0.9300
O1—N1—O2	121.74 (17)	C4—C5—H5A	119.5
O1—N1—C1	118.74 (18)	C6—C5—H5A	119.5
O2—N1—C1	119.52 (17)	N2—C6—C5	120.17 (18)
C6—N2—N3	119.88 (15)	N2—C6—C1	123.59 (16)
C6—N2—H2A	120.1	C5—C6—C1	116.23 (17)
N3—N2—H2A	120.1	N3—C7—C8	125.78 (19)
C7—N3—N2	116.75 (16)	N3—C7—C9	117.37 (19)
C2—C1—C6	121.32 (17)	C8—C7—C9	116.85 (19)
C2—C1—N1	117.08 (18)	C7—C8—H8A	109.5
C6—C1—N1	121.58 (17)	C7—C8—H8B	109.5
C3—C2—C1	120.5 (2)	H8A—C8—H8B	109.5
C3—C2—H2B	119.7	C7—C8—H8C	109.5
C1—C2—H2B	119.7	H8A—C8—H8C	109.5
C2—C3—C4	119.2 (2)	H8B—C8—H8C	109.5
C2—C3—H3B	120.4	C7—C9—H9A	109.5
C4—C3—H3B	120.4	C7—C9—H9B	109.5
C5—C4—C3	121.6 (2)	H9A—C9—H9B	109.5
C5—C4—H4A	119.2	C7—C9—H9C	109.5
C3—C4—H4A	119.2	H9A—C9—H9C	109.5
C4—C5—C6	121.1 (2)	H9B—C9—H9C	109.5
C6—N2—N3—C7	−172.99 (16)	N3—N2—C6—C5	−3.9 (2)
O1—N1—C1—C2	7.5 (2)	N3—N2—C6—C1	175.14 (16)
O2—N1—C1—C2	−172.92 (17)	C4—C5—C6—N2	−179.28 (18)
O1—N1—C1—C6	−171.02 (16)	C4—C5—C6—C1	1.6 (3)
O2—N1—C1—C6	8.6 (3)	C2—C1—C6—N2	179.88 (16)
C6—C1—C2—C3	−0.3 (3)	N1—C1—C6—N2	−1.7 (3)
N1—C1—C2—C3	−178.84 (17)	C2—C1—C6—C5	−1.0 (3)
C1—C2—C3—C4	1.2 (3)	N1—C1—C6—C5	177.40 (16)
C2—C3—C4—C5	−0.6 (3)	N2—N3—C7—C8	0.0 (3)
C3—C4—C5—C6	−0.8 (3)	N2—N3—C7—C9	−179.69 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.00	2.622 (2)	128
C5—H5A···N3	0.93	2.44	2.767 (3)	101
C8—H8A···N2	0.96	2.58	2.780 (3)	92