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Mol­ecules of the title compound, C14H11N5O6, display an E configuration about the C=N bond and an intra­molecular N—H...O hydrogen bond. The crystal packing is consolidated by aromatic π–π stacking and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021271/hb2079sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021271/hb2079Isup2.hkl
Contains datablock I

CCDC reference: 613698

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.155
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - C6 .. 10.46 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N3 .. 6.21 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - N3 .. 6.12 su
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 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 4 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 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).

Acetophenone 2,4,6-trinitrophenylhydrazone top
Crystal data top
C14H11N5O6F(000) = 712
Mr = 345.28Dx = 1.549 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 9868 reflections
a = 10.318 (4) Åθ = 3.1–25.5°
b = 13.850 (5) ŵ = 0.13 mm1
c = 10.385 (4) ÅT = 295 K
β = 93.952 (12)°Prism, red
V = 1480.5 (10) Å30.32 × 0.29 × 0.26 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1313
14339 measured reflectionsk = 1717
3395 independent reflectionsl = 1313
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0859P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
3395 reflectionsΔρmax = 0.25 e Å3
228 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (18)
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
N20.8995 (2)0.83248 (14)0.48185 (18)0.0731 (5)
N10.47405 (16)0.74005 (14)0.30253 (17)0.0671 (5)
N30.81341 (18)0.49156 (14)0.4397 (2)0.0763 (6)
N50.57470 (15)0.44296 (12)0.35829 (16)0.0607 (5)
C70.48823 (18)0.38190 (15)0.31306 (18)0.0588 (5)
O41.00931 (16)0.80898 (12)0.52263 (18)0.0923 (6)
O30.86172 (19)0.91586 (13)0.4727 (2)0.1001 (6)
O20.45507 (15)0.82576 (13)0.28748 (17)0.0880 (5)
O10.38907 (14)0.67913 (12)0.27538 (17)0.0867 (5)
O50.8183 (3)0.45829 (14)0.5447 (2)0.1602 (13)
O60.8495 (2)0.45149 (14)0.3470 (3)0.1410 (10)
C10.63250 (17)0.60800 (14)0.36896 (17)0.0526 (5)
C20.60152 (17)0.70762 (14)0.35419 (18)0.0552 (5)
C30.68810 (19)0.78010 (14)0.39048 (18)0.0571 (5)
H30.66460.84450.37930.069*
C40.80861 (18)0.75615 (14)0.44289 (18)0.0566 (5)
C50.84657 (18)0.66125 (14)0.45915 (18)0.0577 (5)
H50.92920.64610.49480.069*
C60.76091 (17)0.59025 (13)0.42200 (18)0.0536 (5)
N40.54652 (15)0.53838 (12)0.33449 (16)0.0631 (5)
H40.47260.55380.29690.076*
C80.51783 (18)0.27952 (15)0.33804 (18)0.0580 (5)
C90.6399 (2)0.25117 (15)0.3925 (2)0.0662 (6)
H90.70310.29770.41270.079*
C100.6673 (2)0.15611 (16)0.4164 (2)0.0748 (6)
H100.74900.13850.45240.090*
C110.5751 (3)0.08625 (18)0.3877 (2)0.0813 (7)
H110.59370.02170.40550.098*
C120.4567 (3)0.11217 (18)0.3330 (2)0.0852 (7)
H120.39440.06500.31280.102*
C130.4284 (2)0.20731 (17)0.3075 (2)0.0724 (6)
H130.34730.22360.26900.087*
C140.3656 (2)0.41198 (18)0.2379 (3)0.0863 (8)
H14A0.31390.45040.29180.129*
H14B0.31760.35560.20950.129*
H14C0.38680.44920.16430.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0777 (13)0.0691 (13)0.0718 (12)0.0162 (10)0.0007 (10)0.0037 (9)
N10.0543 (10)0.0805 (13)0.0669 (11)0.0117 (9)0.0060 (8)0.0067 (9)
N30.0629 (11)0.0660 (12)0.0980 (16)0.0048 (9)0.0084 (11)0.0061 (11)
N50.0515 (9)0.0659 (11)0.0637 (11)0.0087 (8)0.0037 (8)0.0023 (8)
C70.0476 (10)0.0775 (13)0.0512 (11)0.0085 (10)0.0029 (8)0.0013 (10)
O40.0661 (10)0.0989 (12)0.1096 (14)0.0207 (9)0.0112 (9)0.0039 (10)
O30.1105 (14)0.0632 (11)0.1237 (15)0.0139 (9)0.0127 (11)0.0056 (9)
O20.0745 (10)0.0793 (11)0.1093 (14)0.0220 (8)0.0002 (9)0.0162 (9)
O10.0522 (8)0.0956 (12)0.1098 (13)0.0025 (8)0.0125 (8)0.0024 (10)
O50.272 (3)0.0784 (13)0.1146 (18)0.0258 (15)0.097 (2)0.0010 (12)
O60.1383 (19)0.0721 (12)0.226 (3)0.0032 (11)0.1116 (19)0.0205 (15)
C10.0469 (10)0.0633 (11)0.0476 (10)0.0006 (9)0.0036 (8)0.0025 (9)
C20.0460 (9)0.0696 (13)0.0499 (11)0.0090 (9)0.0035 (8)0.0017 (9)
C30.0619 (11)0.0568 (11)0.0535 (11)0.0041 (9)0.0108 (9)0.0008 (9)
C40.0536 (11)0.0624 (12)0.0534 (12)0.0056 (9)0.0021 (9)0.0038 (9)
C50.0522 (11)0.0663 (13)0.0543 (11)0.0009 (9)0.0004 (9)0.0018 (9)
C60.0475 (10)0.0554 (11)0.0573 (11)0.0039 (8)0.0018 (8)0.0006 (9)
N40.0503 (9)0.0681 (11)0.0692 (11)0.0030 (8)0.0077 (8)0.0007 (8)
C80.0550 (11)0.0721 (13)0.0471 (11)0.0148 (10)0.0054 (9)0.0031 (9)
C90.0611 (12)0.0731 (14)0.0628 (13)0.0151 (10)0.0061 (10)0.0050 (10)
C100.0786 (15)0.0750 (15)0.0695 (15)0.0071 (12)0.0045 (11)0.0093 (11)
C110.0946 (18)0.0709 (15)0.0781 (16)0.0158 (13)0.0051 (14)0.0002 (12)
C120.0854 (17)0.0780 (16)0.0914 (17)0.0320 (13)0.0004 (14)0.0106 (13)
C130.0580 (12)0.0833 (16)0.0753 (15)0.0191 (11)0.0001 (11)0.0065 (12)
C140.0587 (13)0.0928 (17)0.1037 (19)0.0089 (12)0.0203 (13)0.0014 (14)
Geometric parameters (Å, º) top
N1—O11.235 (2)C5—C61.360 (3)
N1—O21.211 (2)C5—H50.9300
N1—C21.457 (2)C7—C81.470 (3)
N2—O31.220 (2)C7—C141.499 (3)
N2—O41.226 (2)C8—C131.383 (3)
N2—C41.452 (3)C8—C91.401 (3)
N3—O51.182 (3)C9—C101.366 (3)
N3—O61.193 (3)C9—H90.9300
N3—C61.477 (3)C10—C111.375 (3)
N4—N51.372 (2)C10—H100.9300
C1—N41.342 (2)C11—C121.360 (4)
N4—H40.8600C11—H110.9300
C7—N51.294 (2)C12—C131.371 (3)
C1—C21.422 (3)C12—H120.9300
C1—C61.421 (3)C13—H130.9300
C2—C31.379 (3)C14—H14A0.9600
C3—C41.364 (3)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C4—C51.379 (3)
O3—N2—O4124.08 (19)C5—C6—N3114.09 (16)
O3—N2—C4118.10 (19)C1—C6—N3122.18 (16)
O4—N2—C4117.82 (19)C1—N4—N5121.07 (16)
O2—N1—O1122.27 (17)C1—N4—H4119.5
O2—N1—C2118.91 (18)N5—N4—H4119.5
O1—N1—C2118.82 (18)C13—C8—C9117.2 (2)
O5—N3—O6124.6 (3)C13—C8—C7122.01 (19)
O5—N3—C6117.8 (2)C9—C8—C7120.78 (17)
O6—N3—C6117.6 (2)C10—C9—C8120.85 (19)
C7—N5—N4115.59 (16)C10—C9—H9119.6
N5—C7—C8115.90 (17)C8—C9—H9119.6
N5—C7—C14122.9 (2)C9—C10—C11120.5 (2)
C8—C7—C14121.17 (17)C9—C10—H10119.8
N4—C1—C6124.10 (18)C11—C10—H10119.8
N4—C1—C2121.92 (17)C12—C11—C10119.5 (2)
C6—C1—C2113.98 (16)C12—C11—H11120.2
C3—C2—C1122.69 (17)C10—C11—H11120.2
C3—C2—N1115.32 (18)C11—C12—C13120.5 (2)
C1—C2—N1121.97 (17)C11—C12—H12119.7
C4—C3—C2119.20 (18)C13—C12—H12119.7
C4—C3—H3120.4C12—C13—C8121.4 (2)
C2—C3—H3120.4C12—C13—H13119.3
C3—C4—C5121.63 (18)C8—C13—H13119.3
C3—C4—N2119.19 (19)C7—C14—H14A109.5
C5—C4—N2119.18 (18)C7—C14—H14B109.5
C6—C5—C4118.75 (17)H14A—C14—H14B109.5
C6—C5—H5120.6C7—C14—H14C109.5
C4—C5—H5120.6H14A—C14—H14C109.5
C5—C6—C1123.73 (18)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.861.942.584 (2)130
C10—H10···O4i0.932.593.388 (3)144
C13—H13···O1ii0.932.533.352 (3)148
C14—H14A···O5iii0.962.583.538 (4)174
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y+1, z+1.
 

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