Acetaldehyde 2,4-dinitro­phenyl­hydrazone

The molecule of the title Schiff base compound, C₈H₈N₄O₄, is not planar, with a dihedral angle of 9.3 (2)° between the N—N=C—C plane and the benzene ring. There is an intra­molecular N—H...O hydrogen bond, and N—O...π inter­actions, which help to stabilize the structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.109
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O4     ..  O4      ..       2.74 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.64 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C2      ..       6.36 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C4      ..       5.19 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Acetaldehyde 2,4-dinitrophenylhydrazone

Crystal data

C8H8N4O4	F(000) = 464
Mr = 224.18	Dx = 1.452 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1171 reflections
a = 5.353 (1) Å	θ = 2.5–23.2°
b = 10.872 (2) Å	µ = 0.12 mm^−1
c = 17.725 (3) Å	T = 298 K
β = 96.160 (4)°	Block, yellow
V = 1025.6 (3) Å^3	0.23 × 0.21 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2120 independent reflections
Radiation source: fine-focus sealed tube	931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→6
Tmin = 0.973, Tmax = 0.979	k = −13→13
8012 measured reflections	l = −22→22

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.82	(Δ/σ)max < 0.001
2120 reflections	Δρmax = 0.11 e Å^−3
150 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (11)

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	1.0387 (4)	0.71714 (18)	0.25089 (12)	0.1041 (7)
O2	0.7968 (4)	0.58125 (17)	0.29564 (11)	0.1024 (7)
O3	0.1840 (3)	0.70454 (13)	0.45230 (9)	0.0806 (5)
O4	0.1116 (3)	0.89524 (13)	0.47687 (8)	0.0716 (5)
N1	0.2253 (3)	0.81436 (18)	0.44493 (10)	0.0605 (5)
N2	0.8626 (4)	0.6876 (2)	0.28634 (12)	0.0812 (7)
N3	0.3401 (3)	1.07261 (16)	0.41126 (10)	0.0615 (5)
N4	0.4084 (4)	1.19253 (17)	0.39546 (10)	0.0698 (6)
C1	0.4647 (4)	0.97750 (19)	0.38321 (11)	0.0538 (5)
C2	0.4158 (4)	0.85239 (18)	0.39675 (11)	0.0527 (6)
C3	0.5433 (4)	0.75829 (19)	0.36465 (12)	0.0602 (6)
H3	0.5056	0.6765	0.3737	0.072*
C4	0.7260 (4)	0.7882 (2)	0.31932 (13)	0.0631 (6)
C5	0.7848 (4)	0.9089 (2)	0.30518 (12)	0.0678 (7)
H5	0.9109	0.9268	0.2746	0.081*
C6	0.6586 (4)	1.0021 (2)	0.33586 (12)	0.0642 (6)
H6	0.6995	1.0831	0.3258	0.077*
C7	0.2675 (6)	1.2753 (2)	0.41693 (14)	0.0797 (8)
H7	0.1271	1.2529	0.4404	0.096*
C8	0.3196 (6)	1.40763 (19)	0.40577 (15)	0.1090 (10)
H8A	0.4675	1.4161	0.3800	0.164*
H8B	0.3456	1.4478	0.4542	0.164*
H8C	0.1793	1.4446	0.3759	0.164*
H3A	0.217 (3)	1.0512 (18)	0.4393 (10)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0763 (13)	0.1327 (17)	0.1084 (15)	0.0119 (11)	0.0334 (11)	−0.0318 (12)
O2	0.1003 (15)	0.0772 (13)	0.1329 (17)	0.0153 (11)	0.0268 (12)	−0.0308 (12)
O3	0.0993 (13)	0.0424 (9)	0.1056 (13)	−0.0030 (9)	0.0368 (10)	0.0012 (9)
O4	0.0820 (11)	0.0511 (9)	0.0872 (11)	0.0079 (8)	0.0341 (9)	−0.0033 (8)
N1	0.0666 (13)	0.0479 (11)	0.0680 (13)	0.0043 (10)	0.0114 (10)	−0.0002 (10)
N2	0.0694 (15)	0.0937 (18)	0.0805 (16)	0.0128 (14)	0.0076 (12)	−0.0277 (14)
N3	0.0710 (13)	0.0428 (11)	0.0733 (14)	−0.0003 (9)	0.0199 (10)	0.0031 (9)
N4	0.0850 (14)	0.0422 (11)	0.0825 (14)	−0.0003 (10)	0.0105 (11)	0.0049 (10)
C1	0.0562 (13)	0.0501 (13)	0.0553 (14)	0.0056 (11)	0.0069 (11)	−0.0003 (11)
C2	0.0554 (13)	0.0461 (13)	0.0578 (14)	0.0027 (11)	0.0116 (11)	−0.0020 (10)
C3	0.0621 (15)	0.0510 (13)	0.0670 (15)	0.0034 (11)	0.0042 (12)	−0.0067 (11)
C4	0.0589 (15)	0.0650 (16)	0.0656 (16)	0.0116 (12)	0.0077 (12)	−0.0141 (12)
C5	0.0608 (15)	0.0796 (19)	0.0649 (15)	0.0013 (13)	0.0157 (12)	−0.0009 (13)
C6	0.0676 (15)	0.0585 (15)	0.0676 (16)	−0.0018 (12)	0.0127 (13)	0.0046 (12)
C7	0.115 (2)	0.0480 (15)	0.0790 (18)	0.0047 (15)	0.0225 (15)	0.0071 (12)
C8	0.174 (3)	0.0480 (16)	0.104 (2)	0.0041 (16)	0.013 (2)	0.0038 (14)

Geometric parameters (Å, º)

O1—N2	1.231 (3)	C2—C3	1.385 (3)
O2—N2	1.225 (2)	C3—C4	1.370 (3)
O3—N1	1.224 (2)	C3—H3	0.9300
O4—N1	1.240 (2)	C4—C5	1.379 (3)
N1—C2	1.458 (2)	C5—C6	1.363 (3)
N2—C4	1.471 (3)	C5—H5	0.9300
N3—C1	1.354 (2)	C6—H6	0.9300
N3—N4	1.391 (2)	C7—C8	1.483 (3)
N3—H3A	0.899 (9)	C7—H7	0.9300
N4—C7	1.259 (3)	C8—H8A	0.9600
C1—C2	1.411 (3)	C8—H8B	0.9600
C1—C6	1.428 (3)	C8—H8C	0.9600
O3—N1—O4	122.66 (18)	C3—C4—C5	121.6 (2)
O3—N1—C2	119.01 (18)	C3—C4—N2	118.2 (2)
O4—N1—C2	118.33 (17)	C5—C4—N2	120.2 (2)
O2—N2—O1	124.2 (2)	C6—C5—C4	120.2 (2)
O2—N2—C4	119.1 (2)	C6—C5—H5	119.9
O1—N2—C4	116.7 (2)	C4—C5—H5	119.9
C1—N3—N4	119.45 (18)	C5—C6—C1	121.2 (2)
C1—N3—H3A	115.2 (14)	C5—C6—H6	119.4
N4—N3—H3A	125.4 (13)	C1—C6—H6	119.4
C7—N4—N3	115.5 (2)	N4—C7—C8	121.7 (3)
N3—C1—C2	124.50 (18)	N4—C7—H7	119.1
N3—C1—C6	119.39 (19)	C8—C7—H7	119.1
C2—C1—C6	116.10 (19)	C7—C8—H8A	109.5
C3—C2—C1	122.26 (19)	C7—C8—H8B	109.5
C3—C2—N1	115.92 (18)	H8A—C8—H8B	109.5
C1—C2—N1	121.81 (18)	C7—C8—H8C	109.5
C4—C3—C2	118.7 (2)	H8A—C8—H8C	109.5
C4—C3—H3	120.7	H8B—C8—H8C	109.5
C2—C3—H3	120.7
C1—N3—N4—C7	173.0 (2)	C2—C3—C4—C5	0.0 (3)
N4—N3—C1—C2	178.58 (18)	C2—C3—C4—N2	179.19 (18)
N4—N3—C1—C6	−2.0 (3)	O2—N2—C4—C3	5.4 (3)
N3—C1—C2—C3	177.8 (2)	O1—N2—C4—C3	−174.4 (2)
C6—C1—C2—C3	−1.6 (3)	O2—N2—C4—C5	−175.4 (2)
N3—C1—C2—N1	−1.5 (3)	O1—N2—C4—C5	4.8 (3)
C6—C1—C2—N1	179.11 (18)	C3—C4—C5—C6	−0.7 (3)
O3—N1—C2—C3	−2.2 (3)	N2—C4—C5—C6	−179.9 (2)
O4—N1—C2—C3	177.78 (18)	C4—C5—C6—C1	0.2 (3)
O3—N1—C2—C1	177.16 (18)	N3—C1—C6—C5	−178.58 (19)
O4—N1—C2—C1	−2.9 (3)	C2—C1—C6—C5	0.9 (3)
C1—C2—C3—C4	1.2 (3)	N3—N4—C7—C8	178.5 (2)
N1—C2—C3—C4	−179.46 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.90 (1)	1.93 (2)	2.622 (2)	133 (2)