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Crystals of the title compound, C13H10N4O4, were obtained from a condensation reaction of 2-nitro­benz­aldehyde and 4-nitrophenylhydrazine. Significantly different C—N(nitro) and N—O bond distances are observed for the o- and p-nitro groups. The aromatic C—C bonds close to the imino group are longer than the others in the same benzene ring. The overlapped arrangement of nearly parallel benzene rings from neighboring mol­ecules and centroid-to-centroid distance of 3.9370 (9) Å suggest π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024572/cv6384sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024572/cv6384Isup2.hkl
Contains datablock I

CCDC reference: 255875

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - N3 .. 5.51 su
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 1 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Nitrobenzaldehyde 4-nitrophenylhydrazone top
Crystal data top
C13H10N4O4F(000) = 592
Mr = 286.25Dx = 1.503 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9018 reflections
a = 7.2570 (7) Åθ = 2.5–25.0°
b = 12.0869 (11) ŵ = 0.12 mm1
c = 14.4455 (11) ÅT = 295 K
β = 93.465 (2)°Prism, red
V = 1264.77 (19) Å30.31 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1936 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.5°, θmin = 2.2°
Detector resolution: 10.00 pixels mm-1h = 88
ω scansk = 1414
9588 measured reflectionsl = 1717
2322 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0518P)2 + 0.2408P]
where P = (Fo2 + 2Fc2)/3
2322 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.00642 (17)0.19208 (10)0.30321 (7)0.0594 (3)
O20.03558 (17)0.05519 (9)0.39773 (8)0.0607 (3)
O30.7286 (2)0.66890 (10)0.82471 (9)0.0731 (4)
O40.7094 (2)0.83026 (11)0.88241 (9)0.0778 (4)
N10.34927 (19)0.44231 (9)0.64730 (8)0.0460 (3)
H10.38370.41640.70100.055*
N20.37078 (17)0.55105 (9)0.62929 (8)0.0421 (3)
N30.04482 (17)0.15383 (11)0.38014 (8)0.0446 (3)
N40.67471 (18)0.76378 (11)0.82075 (9)0.0479 (3)
C10.27283 (19)0.37307 (11)0.58029 (9)0.0374 (3)
C20.2606 (2)0.26020 (12)0.60004 (10)0.0420 (4)
H20.30510.23360.65750.050*
C30.1835 (2)0.18865 (11)0.53533 (10)0.0409 (3)
H30.17470.11360.54860.049*
C40.11859 (19)0.22946 (12)0.44984 (9)0.0380 (3)
C50.1285 (2)0.34100 (12)0.42940 (10)0.0445 (4)
H50.08300.36700.37190.053*
C60.2053 (2)0.41295 (12)0.49376 (10)0.0442 (4)
H60.21270.48800.48010.053*
C70.4481 (2)0.60993 (12)0.69375 (10)0.0413 (3)
H70.48830.57850.75020.050*
C80.47217 (19)0.72834 (11)0.67676 (9)0.0369 (3)
C90.5683 (2)0.80205 (12)0.73694 (10)0.0389 (3)
C100.5749 (2)0.91451 (12)0.71953 (11)0.0483 (4)
H100.63740.96140.76170.058*
C110.4892 (2)0.95664 (13)0.64008 (12)0.0536 (4)
H110.49321.03220.62810.064*
C120.3967 (2)0.88605 (14)0.57783 (11)0.0503 (4)
H120.34030.91410.52330.060*
C130.3879 (2)0.77497 (12)0.59618 (10)0.0433 (4)
H130.32380.72910.55370.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0741 (8)0.0619 (8)0.0403 (6)0.0080 (6)0.0126 (5)0.0080 (5)
O20.0793 (8)0.0382 (7)0.0637 (7)0.0127 (6)0.0029 (6)0.0122 (5)
O30.0909 (10)0.0414 (7)0.0814 (9)0.0032 (6)0.0398 (8)0.0048 (6)
O40.1083 (11)0.0645 (9)0.0564 (7)0.0029 (7)0.0283 (7)0.0188 (6)
N10.0693 (8)0.0285 (6)0.0381 (6)0.0049 (6)0.0134 (6)0.0021 (5)
N20.0546 (7)0.0296 (6)0.0412 (6)0.0042 (5)0.0052 (6)0.0011 (5)
N30.0461 (7)0.0455 (8)0.0421 (7)0.0050 (6)0.0006 (6)0.0092 (6)
N40.0535 (8)0.0430 (8)0.0458 (7)0.0071 (6)0.0084 (6)0.0032 (6)
C10.0444 (8)0.0302 (7)0.0372 (7)0.0007 (6)0.0026 (6)0.0010 (6)
C20.0547 (9)0.0330 (8)0.0371 (7)0.0002 (6)0.0065 (7)0.0023 (6)
C30.0514 (8)0.0264 (7)0.0446 (8)0.0012 (6)0.0001 (7)0.0005 (6)
C40.0410 (7)0.0355 (8)0.0372 (7)0.0026 (6)0.0000 (6)0.0060 (6)
C50.0572 (9)0.0409 (8)0.0341 (7)0.0024 (7)0.0064 (7)0.0034 (6)
C60.0602 (9)0.0288 (7)0.0425 (8)0.0033 (6)0.0057 (7)0.0042 (6)
C70.0517 (8)0.0332 (8)0.0380 (7)0.0015 (6)0.0061 (6)0.0003 (6)
C80.0409 (7)0.0313 (7)0.0382 (7)0.0005 (6)0.0008 (6)0.0013 (5)
C90.0426 (8)0.0327 (7)0.0410 (7)0.0004 (6)0.0000 (6)0.0017 (6)
C100.0535 (9)0.0320 (8)0.0588 (9)0.0058 (7)0.0004 (8)0.0078 (7)
C110.0595 (10)0.0296 (8)0.0716 (11)0.0001 (7)0.0034 (8)0.0088 (7)
C120.0528 (9)0.0446 (9)0.0527 (9)0.0033 (7)0.0020 (7)0.0132 (7)
C130.0464 (8)0.0401 (8)0.0427 (8)0.0026 (6)0.0027 (6)0.0009 (6)
Geometric parameters (Å, º) top
O1—N31.2397 (16)C4—C51.383 (2)
O2—N31.2217 (16)C5—C61.367 (2)
O3—N41.2120 (17)C5—H50.9300
O4—N41.2145 (16)C6—H60.9300
N1—N21.3506 (16)C7—C81.464 (2)
N1—C11.3712 (17)C7—H70.9300
N1—H10.8600C8—C91.4012 (19)
N2—C71.2750 (17)C8—C131.400 (2)
N3—C41.4390 (17)C9—C101.384 (2)
N4—C91.4706 (19)C10—C111.370 (2)
C1—C21.398 (2)C10—H100.9300
C1—C61.4002 (19)C11—C121.384 (2)
C2—C31.3680 (19)C11—H110.9300
C2—H20.9300C12—C131.371 (2)
C3—C41.386 (2)C12—H120.9300
C3—H30.9300C13—H130.9300
N2—N1—C1120.30 (12)C5—C6—C1119.63 (13)
N2—N1—H1119.9C5—C6—H6120.2
C1—N1—H1119.9C1—C6—H6120.2
C7—N2—N1116.97 (12)N2—C7—C8118.35 (13)
O2—N3—O1122.21 (12)N2—C7—H7120.8
O2—N3—C4119.81 (12)C8—C7—H7120.8
O1—N3—C4117.97 (13)C13—C8—C9115.85 (13)
O3—N4—O4122.65 (14)C13—C8—C7118.83 (12)
O3—N4—C9119.23 (12)C9—C8—C7125.27 (12)
O4—N4—C9118.08 (13)C10—C9—C8122.22 (13)
N1—C1—C2118.66 (12)C10—C9—N4115.88 (13)
N1—C1—C6121.66 (13)C8—C9—N4121.85 (12)
C2—C1—C6119.68 (12)C11—C10—C9119.90 (14)
C3—C2—C1120.40 (13)C11—C10—H10120.0
C3—C2—H2119.8C9—C10—H10120.0
C1—C2—H2119.8C10—C11—C12119.54 (14)
C2—C3—C4119.13 (13)C10—C11—H11120.2
C2—C3—H3120.4C12—C11—H11120.2
C4—C3—H3120.4C13—C12—C11120.33 (14)
C5—C4—C3121.20 (13)C13—C12—H12119.8
C5—C4—N3119.46 (12)C11—C12—H12119.8
C3—C4—N3119.31 (13)C12—C13—C8122.12 (14)
C6—C5—C4119.96 (13)C12—C13—H13118.9
C6—C5—H5120.0C8—C13—H13118.9
C4—C5—H5120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.102.9193 (16)160
C7—H7···O30.932.272.787 (2)114
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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