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The crystals of the title compound, C14H11N5O6, were obtained from a condensation reaction of 4-methyl­benzaldehyde and 2,4,6-trinitro­phenyl­hydrazine. The mol­ecule displays an E configuration. The centroid-to-centroid separation of 3.885 (2) Å indicates the existence of π–π stacking between nearly parallel benzene rings of neighboring mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014511/xu2232sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014511/xu2232Isup2.hkl
Contains datablock I

CCDC reference: 647475

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.066
  • wR factor = 0.245
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

(E)-4-Methylbenzaldehyde 2,4,6-trinitrophenylhydrazone top
Crystal data top
C14H11N5O6Z = 2
Mr = 345.28F(000) = 356
Triclinic, P1Dx = 1.502 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.1378 (12) ÅCell parameters from 3722 reflections
b = 7.4914 (14) Åθ = 3.0–24.0°
c = 14.9950 (19) ŵ = 0.12 mm1
α = 76.191 (9)°T = 294 K
β = 79.469 (7)°Platelet, red
γ = 83.606 (6)°0.31 × 0.23 × 0.12 mm
V = 763.6 (2) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.2°, θmin = 3.0°
Detector resolution: 10.00 pixels mm-1h = 88
ω scansk = 88
6162 measured reflectionsl = 1717
2746 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.245 w = 1/[σ2(Fo2) + (0.1447P)2 + 0.1109P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2746 reflectionsΔρmax = 0.40 e Å3
228 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.054 (14)
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
N10.6114 (4)0.1892 (4)0.52131 (18)0.0493 (7)
H10.72290.14080.53110.059*
N20.5662 (4)0.2217 (4)0.43359 (17)0.0485 (7)
N30.2153 (4)0.3276 (4)0.49666 (18)0.0491 (7)
N40.0855 (5)0.3848 (5)0.8165 (2)0.0676 (9)
N50.7168 (4)0.1386 (4)0.70487 (19)0.0554 (8)
O10.2100 (4)0.4817 (4)0.44641 (18)0.0690 (8)
O20.1511 (4)0.1950 (4)0.48287 (17)0.0646 (8)
O30.0608 (4)0.4750 (5)0.7974 (2)0.0898 (10)
O40.1261 (5)0.3399 (6)0.8947 (2)0.0992 (12)
O50.7520 (4)0.1353 (5)0.78136 (19)0.0858 (10)
O60.8365 (4)0.0825 (4)0.64516 (17)0.0682 (8)
C10.4843 (4)0.2317 (4)0.5921 (2)0.0439 (8)
C20.2939 (5)0.3045 (4)0.5833 (2)0.0462 (8)
C30.1674 (5)0.3564 (5)0.6545 (2)0.0520 (9)
H30.04550.40670.64530.062*
C40.2227 (5)0.3334 (5)0.7401 (2)0.0528 (9)
C50.4005 (5)0.2599 (5)0.7556 (2)0.0522 (9)
H50.43420.24210.81430.063*
C60.5303 (5)0.2120 (4)0.6830 (2)0.0460 (8)
C70.7018 (5)0.1870 (5)0.3704 (2)0.0493 (8)
H70.82240.14780.38580.059*
C80.6721 (5)0.2072 (5)0.2746 (2)0.0494 (8)
C90.4952 (5)0.2638 (5)0.2473 (2)0.0559 (9)
H90.39240.29510.29000.067*
C100.4718 (6)0.2736 (6)0.1565 (3)0.0676 (11)
H100.35260.31110.13900.081*
C110.6227 (7)0.2286 (6)0.0914 (2)0.0675 (11)
C120.7975 (6)0.1746 (6)0.1189 (3)0.0711 (12)
H120.90050.14530.07580.085*
C130.8235 (6)0.1630 (5)0.2090 (2)0.0619 (10)
H130.94310.12530.22600.074*
C140.5946 (9)0.2396 (8)0.0075 (3)0.0959 (16)
H14A0.67030.33260.04930.144*
H14B0.46220.27050.01270.144*
H14C0.63340.12260.02330.144*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0422 (15)0.0644 (17)0.0425 (14)0.0034 (13)0.0104 (11)0.0148 (13)
N20.0501 (16)0.0564 (16)0.0396 (14)0.0027 (12)0.0082 (12)0.0116 (13)
N30.0428 (16)0.0580 (18)0.0453 (15)0.0019 (13)0.0099 (12)0.0095 (14)
N40.057 (2)0.087 (2)0.060 (2)0.0005 (17)0.0010 (15)0.0286 (18)
N50.0497 (17)0.0717 (19)0.0483 (16)0.0027 (14)0.0160 (13)0.0173 (15)
O10.0769 (19)0.0635 (17)0.0630 (15)0.0037 (13)0.0259 (13)0.0004 (13)
O20.0670 (17)0.0753 (17)0.0593 (15)0.0119 (13)0.0171 (12)0.0219 (13)
O30.0590 (18)0.125 (3)0.087 (2)0.0197 (18)0.0034 (15)0.046 (2)
O40.090 (2)0.153 (3)0.0539 (16)0.013 (2)0.0026 (16)0.0395 (19)
O50.0640 (18)0.145 (3)0.0596 (16)0.0196 (18)0.0307 (13)0.0414 (18)
O60.0483 (15)0.103 (2)0.0545 (14)0.0159 (14)0.0135 (12)0.0254 (14)
C10.0416 (17)0.0472 (17)0.0435 (16)0.0052 (13)0.0056 (13)0.0115 (14)
C20.0442 (18)0.0507 (18)0.0441 (16)0.0018 (14)0.0094 (14)0.0105 (14)
C30.0423 (18)0.0561 (19)0.058 (2)0.0007 (15)0.0086 (15)0.0150 (16)
C40.050 (2)0.062 (2)0.0469 (18)0.0012 (16)0.0045 (15)0.0176 (16)
C50.057 (2)0.059 (2)0.0428 (17)0.0069 (16)0.0079 (15)0.0127 (15)
C60.0400 (17)0.0513 (17)0.0481 (17)0.0030 (14)0.0103 (14)0.0114 (15)
C70.0433 (18)0.0560 (19)0.0475 (18)0.0003 (14)0.0072 (14)0.0112 (15)
C80.053 (2)0.0515 (18)0.0405 (16)0.0020 (15)0.0019 (14)0.0084 (15)
C90.053 (2)0.067 (2)0.0450 (18)0.0018 (17)0.0068 (15)0.0121 (17)
C100.067 (3)0.082 (3)0.053 (2)0.002 (2)0.0169 (18)0.0120 (19)
C110.084 (3)0.072 (2)0.0428 (19)0.005 (2)0.0074 (19)0.0082 (18)
C120.074 (3)0.088 (3)0.0453 (19)0.006 (2)0.0024 (18)0.018 (2)
C130.056 (2)0.071 (2)0.0531 (19)0.0041 (18)0.0027 (16)0.0118 (18)
C140.127 (5)0.111 (4)0.050 (2)0.006 (3)0.017 (3)0.017 (2)
Geometric parameters (Å, º) top
N1—C11.341 (4)C5—C61.385 (5)
N1—N21.370 (3)C5—H50.9300
N1—H10.8600C7—C81.460 (4)
N2—C71.276 (4)C7—H70.9300
N3—O21.214 (4)C8—C91.389 (5)
N3—O11.220 (4)C8—C131.390 (5)
N3—C21.473 (4)C9—C101.385 (5)
N4—O41.219 (4)C9—H90.9300
N4—O31.219 (4)C10—C111.386 (6)
N4—C41.462 (4)C10—H100.9300
N5—O51.212 (3)C11—C121.373 (6)
N5—O61.236 (4)C11—C141.514 (5)
N5—C61.447 (4)C12—C131.378 (5)
C1—C21.424 (4)C12—H120.9300
C1—C61.429 (4)C13—H130.9300
C2—C31.370 (4)C14—H14A0.9600
C3—C41.377 (5)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C4—C51.363 (5)
C1—N1—N2121.0 (3)C5—C6—N5115.7 (3)
C1—N1—H1119.5C1—C6—N5121.7 (3)
N2—N1—H1119.5N2—C7—C8121.6 (3)
C7—N2—N1115.6 (3)N2—C7—H7119.2
O2—N3—O1124.7 (3)C8—C7—H7119.2
O2—N3—C2117.9 (3)C9—C8—C13118.6 (3)
O1—N3—C2117.3 (3)C9—C8—C7122.0 (3)
O4—N4—O3124.0 (3)C13—C8—C7119.3 (3)
O4—N4—C4118.3 (3)C10—C9—C8120.1 (3)
O3—N4—C4117.7 (3)C10—C9—H9120.0
O5—N5—O6121.7 (3)C8—C9—H9120.0
O5—N5—C6118.9 (3)C9—C10—C11121.2 (4)
O6—N5—C6119.4 (3)C9—C10—H10119.4
N1—C1—C2123.3 (3)C11—C10—H10119.4
N1—C1—C6122.6 (3)C12—C11—C10118.2 (3)
C2—C1—C6114.1 (3)C12—C11—C14121.2 (4)
C3—C2—C1123.2 (3)C10—C11—C14120.5 (4)
C3—C2—N3114.2 (3)C11—C12—C13121.4 (3)
C1—C2—N3122.6 (3)C11—C12—H12119.3
C2—C3—C4119.3 (3)C13—C12—H12119.3
C2—C3—H3120.4C12—C13—C8120.4 (4)
C4—C3—H3120.4C12—C13—H13119.8
C5—C4—C3121.5 (3)C8—C13—H13119.8
C5—C4—N4119.5 (3)C11—C14—H14A109.5
C3—C4—N4119.0 (3)C11—C14—H14B109.5
C4—C5—C6119.3 (3)H14A—C14—H14B109.5
C4—C5—H5120.3C11—C14—H14C109.5
C6—C5—H5120.3H14A—C14—H14C109.5
C5—C6—C1122.6 (3)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O60.861.962.601 (4)130
C3—H3···O1i0.932.443.302 (5)155
Symmetry code: (i) x, y+1, z+1.
 

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