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Crystals of the title compound {systematic name [(1E)-1-aza-2-(3-chloro­phen­yl)prop-1-en­yl](2,4,6-trinitro­phen­yl)amine}, C14H10ClN5O6, were obtained from a condensation reaction of 3-chloro­acetophenone and 2,4,6-trinitro­phenylhydrazine. There are two molecules in the asymmetric unit. The double bond in the bridge between the benzene rings displays an E configuration. π–π stacking is observed between parallel and nearly parallel benzene rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005952/gh6033sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005952/gh6033Isup2.hkl
Contains datablock I

CCDC reference: 601171

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.147
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT414_ALERT_2_C Short Intra D-H..H-X H9 .. H21C .. 1.98 Ang.
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 and 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).

[(1E)-1-aza-2-(3-chlorophenyl)prop-1-enyl](2,4,6-trinitrophenyl)amine top
Crystal data top
C14H10ClN5O6F(000) = 1552
Mr = 379.72Dx = 1.599 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 12806 reflections
a = 13.1335 (5) Åθ = 2.3–24.5°
b = 24.5909 (8) ŵ = 0.29 mm1
c = 10.0806 (3) ÅT = 295 K
β = 104.328 (2)°Prism, yellow
V = 3154.41 (18) Å30.38 × 0.36 × 0.28 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4052 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 25.9°, θmin = 1.6°
Detector resolution: 10.00 pixels mm-1h = 1616
ω scansk = 3030
25647 measured reflectionsl = 1112
6085 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0873P)2]
where P = (Fo2 + 2Fc2)/3
6085 reflections(Δ/σ)max = 0.001
471 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.25 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
C10.46513 (19)0.70954 (9)0.2948 (2)0.0353 (5)
C20.39933 (19)0.67921 (9)0.3589 (2)0.0355 (5)
C30.4036 (2)0.62405 (9)0.3721 (2)0.0394 (6)
H30.36010.60590.41750.047*
C40.4740 (2)0.59569 (9)0.3165 (2)0.0392 (6)
C50.5356 (2)0.62142 (9)0.2456 (2)0.0396 (6)
H50.58070.60150.20610.048*
C60.53051 (19)0.67765 (9)0.2327 (2)0.0373 (5)
C70.4873 (2)0.87273 (10)0.2695 (3)0.0496 (7)
H7A0.55990.86600.31270.074*
H7B0.47470.91120.26370.074*
H7C0.47040.85740.17910.074*
C80.4198 (2)0.84704 (9)0.3521 (2)0.0395 (6)
C90.3575 (2)0.88030 (9)0.4268 (2)0.0399 (6)
C100.3708 (2)0.93665 (9)0.4367 (2)0.0434 (6)
H100.41980.95360.39800.052*
C110.3110 (2)0.96696 (9)0.5041 (3)0.0474 (7)
C120.2378 (2)0.94389 (11)0.5625 (3)0.0537 (7)
H120.19800.96520.60700.064*
C130.2245 (2)0.88814 (11)0.5537 (3)0.0552 (7)
H130.17590.87170.59400.066*
C140.2827 (2)0.85642 (10)0.4856 (3)0.0482 (6)
H140.27180.81900.47900.058*
C150.9491 (2)0.40328 (10)0.2994 (2)0.0399 (6)
C160.89910 (19)0.37352 (9)0.3866 (2)0.0383 (6)
C170.9101 (2)0.31873 (10)0.4057 (2)0.0420 (6)
H170.87800.30100.46600.050*
C180.9692 (2)0.29004 (9)0.3345 (2)0.0416 (6)
C191.0194 (2)0.31541 (10)0.2479 (2)0.0429 (6)
H191.05920.29550.20050.051*
C201.0100 (2)0.37112 (10)0.2321 (2)0.0422 (6)
C210.9244 (3)0.56395 (11)0.2102 (3)0.0636 (9)
H21A0.99950.56730.23790.095*
H21B0.89370.59920.18670.095*
H21C0.90510.54040.13210.095*
C220.8850 (2)0.54056 (10)0.3256 (2)0.0423 (6)
C230.8323 (2)0.57595 (10)0.4071 (2)0.0428 (6)
C240.8312 (2)0.63211 (10)0.3898 (3)0.0467 (6)
H240.86420.64760.32720.056*
C250.7815 (2)0.66478 (10)0.4652 (3)0.0502 (7)
C260.7324 (2)0.64364 (11)0.5588 (3)0.0557 (7)
H260.69990.66640.60970.067*
C270.7320 (2)0.58791 (12)0.5760 (3)0.0592 (8)
H270.69830.57290.63840.071*
C280.7811 (2)0.55419 (11)0.5016 (3)0.0525 (7)
H280.78030.51670.51430.063*
N10.31223 (17)0.70550 (8)0.4046 (2)0.0428 (5)
N20.4779 (2)0.53659 (8)0.3279 (2)0.0504 (6)
N30.59322 (19)0.70138 (9)0.1476 (2)0.0486 (6)
N40.46868 (18)0.76441 (7)0.2944 (2)0.0433 (5)
H40.50740.78060.24910.052*
N50.41164 (17)0.79493 (7)0.3649 (2)0.0412 (5)
N60.82527 (19)0.39936 (8)0.4561 (2)0.0453 (5)
N70.97812 (19)0.23115 (9)0.3502 (2)0.0521 (6)
N81.0704 (2)0.39513 (10)0.1430 (2)0.0528 (6)
N90.94109 (18)0.45768 (8)0.2830 (2)0.0469 (5)
H90.96750.47260.22200.056*
N100.89281 (17)0.48998 (8)0.3593 (2)0.0449 (5)
O10.24003 (17)0.72294 (8)0.3165 (2)0.0674 (6)
O20.31653 (18)0.70560 (8)0.5262 (2)0.0620 (6)
O30.4128 (2)0.51429 (8)0.3766 (2)0.0742 (7)
O40.54519 (19)0.51264 (7)0.2864 (2)0.0695 (6)
O50.58906 (18)0.75129 (7)0.1285 (2)0.0638 (6)
O60.64629 (19)0.67178 (8)0.0953 (2)0.0706 (6)
O70.74061 (16)0.41350 (8)0.3879 (2)0.0622 (5)
O80.8504 (2)0.40160 (10)0.5792 (2)0.0812 (7)
O90.94384 (18)0.21048 (7)0.4408 (2)0.0630 (6)
O101.0173 (2)0.20580 (8)0.2720 (3)0.0781 (7)
O111.0568 (2)0.44366 (9)0.1117 (2)0.0757 (7)
O121.13202 (19)0.36699 (9)0.1031 (2)0.0704 (6)
Cl10.32896 (7)1.03714 (3)0.51245 (9)0.0702 (3)
Cl20.78205 (7)0.73499 (3)0.44101 (9)0.0684 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0398 (14)0.0285 (11)0.0368 (12)0.0002 (10)0.0083 (10)0.0001 (9)
C20.0370 (14)0.0306 (11)0.0389 (12)0.0026 (10)0.0095 (10)0.0047 (10)
C30.0448 (15)0.0331 (12)0.0430 (13)0.0060 (11)0.0160 (11)0.0006 (10)
C40.0461 (16)0.0276 (11)0.0444 (13)0.0033 (10)0.0119 (11)0.0020 (10)
C50.0451 (15)0.0332 (12)0.0428 (12)0.0009 (10)0.0150 (11)0.0053 (10)
C60.0407 (14)0.0341 (12)0.0390 (12)0.0050 (10)0.0137 (10)0.0014 (10)
C70.0608 (19)0.0310 (12)0.0613 (16)0.0057 (12)0.0234 (14)0.0018 (12)
C80.0440 (15)0.0295 (12)0.0435 (13)0.0020 (10)0.0079 (11)0.0001 (10)
C90.0458 (15)0.0310 (12)0.0413 (12)0.0005 (10)0.0078 (11)0.0004 (10)
C100.0473 (16)0.0326 (12)0.0499 (14)0.0030 (11)0.0113 (12)0.0001 (11)
C110.0527 (17)0.0292 (12)0.0560 (15)0.0010 (11)0.0055 (13)0.0043 (11)
C120.0537 (18)0.0458 (15)0.0624 (16)0.0036 (13)0.0162 (14)0.0070 (13)
C130.0561 (19)0.0478 (15)0.0662 (17)0.0047 (13)0.0236 (15)0.0003 (14)
C140.0581 (18)0.0331 (12)0.0547 (15)0.0026 (12)0.0166 (13)0.0008 (11)
C150.0418 (15)0.0411 (13)0.0378 (12)0.0029 (11)0.0120 (11)0.0038 (11)
C160.0362 (14)0.0404 (13)0.0404 (12)0.0031 (10)0.0138 (11)0.0024 (11)
C170.0390 (15)0.0419 (13)0.0475 (13)0.0064 (11)0.0151 (11)0.0028 (11)
C180.0418 (15)0.0353 (12)0.0484 (14)0.0024 (11)0.0126 (12)0.0012 (11)
C190.0431 (15)0.0447 (14)0.0441 (13)0.0003 (11)0.0168 (11)0.0046 (11)
C200.0455 (16)0.0434 (14)0.0421 (12)0.0029 (11)0.0191 (11)0.0027 (11)
C210.094 (3)0.0457 (15)0.0605 (17)0.0055 (16)0.0372 (17)0.0028 (14)
C220.0410 (15)0.0383 (13)0.0467 (13)0.0055 (11)0.0089 (11)0.0008 (11)
C230.0431 (15)0.0373 (13)0.0480 (13)0.0064 (11)0.0114 (12)0.0021 (11)
C240.0425 (16)0.0389 (13)0.0601 (15)0.0056 (11)0.0154 (12)0.0020 (12)
C250.0421 (16)0.0356 (13)0.0707 (17)0.0017 (11)0.0100 (14)0.0028 (13)
C260.0480 (18)0.0502 (15)0.0727 (18)0.0018 (13)0.0221 (15)0.0112 (14)
C270.063 (2)0.0490 (16)0.0741 (19)0.0130 (14)0.0335 (16)0.0074 (14)
C280.0633 (19)0.0372 (13)0.0620 (16)0.0081 (13)0.0248 (14)0.0014 (13)
N10.0392 (13)0.0316 (10)0.0601 (14)0.0048 (9)0.0168 (11)0.0044 (10)
N20.0665 (17)0.0300 (11)0.0579 (13)0.0030 (11)0.0211 (12)0.0006 (10)
N30.0547 (15)0.0404 (12)0.0563 (13)0.0047 (10)0.0242 (11)0.0003 (10)
N40.0550 (14)0.0271 (10)0.0534 (12)0.0031 (9)0.0242 (11)0.0012 (9)
N50.0503 (14)0.0284 (10)0.0476 (11)0.0001 (9)0.0172 (10)0.0000 (9)
N60.0501 (15)0.0392 (12)0.0512 (13)0.0042 (10)0.0210 (11)0.0003 (10)
N70.0529 (15)0.0400 (12)0.0639 (15)0.0025 (11)0.0155 (12)0.0020 (11)
N80.0622 (16)0.0542 (14)0.0511 (13)0.0026 (12)0.0316 (12)0.0020 (11)
N90.0585 (15)0.0378 (11)0.0520 (12)0.0019 (10)0.0278 (11)0.0063 (10)
N100.0498 (14)0.0354 (11)0.0536 (12)0.0008 (10)0.0204 (11)0.0003 (10)
O10.0432 (12)0.0638 (13)0.0872 (15)0.0079 (10)0.0008 (11)0.0099 (11)
O20.0766 (15)0.0589 (12)0.0635 (12)0.0047 (10)0.0420 (11)0.0007 (10)
O30.0914 (18)0.0372 (10)0.1057 (17)0.0090 (11)0.0466 (14)0.0115 (11)
O40.0905 (17)0.0352 (10)0.0938 (15)0.0099 (10)0.0435 (13)0.0077 (10)
O50.0828 (16)0.0407 (10)0.0825 (14)0.0080 (10)0.0481 (12)0.0054 (10)
O60.0830 (17)0.0555 (12)0.0938 (15)0.0049 (11)0.0603 (14)0.0016 (11)
O70.0420 (12)0.0639 (12)0.0812 (14)0.0025 (10)0.0161 (11)0.0085 (11)
O80.100 (2)0.1028 (18)0.0442 (12)0.0294 (14)0.0247 (12)0.0022 (11)
O90.0691 (15)0.0465 (11)0.0740 (13)0.0050 (10)0.0189 (11)0.0124 (10)
O100.0954 (19)0.0447 (12)0.1082 (18)0.0075 (11)0.0514 (15)0.0090 (12)
O110.1077 (19)0.0542 (12)0.0867 (15)0.0084 (12)0.0645 (14)0.0221 (11)
O120.0841 (17)0.0658 (13)0.0804 (14)0.0036 (12)0.0567 (13)0.0009 (11)
Cl10.0747 (6)0.0325 (3)0.1065 (6)0.0005 (3)0.0282 (5)0.0128 (4)
Cl20.0710 (6)0.0369 (4)0.1013 (6)0.0049 (3)0.0290 (5)0.0011 (4)
Geometric parameters (Å, º) top
C1—N41.350 (3)C18—N71.458 (3)
C1—C21.413 (3)C19—C201.381 (3)
C1—C61.417 (3)C19—H190.9300
C2—C31.363 (3)C20—N81.462 (3)
C2—N11.483 (3)C21—C221.500 (4)
C3—C41.382 (3)C21—H21A0.9600
C3—H30.9300C21—H21B0.9600
C4—C51.362 (3)C21—H21C0.9600
C4—N21.458 (3)C22—N101.287 (3)
C5—C61.389 (3)C22—C231.481 (4)
C5—H50.9300C23—C241.391 (3)
C6—N31.451 (3)C23—C281.401 (4)
C7—C81.498 (4)C24—C251.377 (4)
C7—H7A0.9600C24—H240.9300
C7—H7B0.9600C25—C261.370 (4)
C7—H7C0.9600C25—Cl21.744 (3)
C8—N51.295 (3)C26—C271.382 (4)
C8—C91.487 (3)C26—H260.9300
C9—C141.396 (4)C27—C281.381 (4)
C9—C101.397 (3)C27—H270.9300
C10—C111.377 (4)C28—H280.9300
C10—H100.9300N1—O11.207 (3)
C11—C121.369 (4)N1—O21.212 (3)
C11—Cl11.741 (2)N2—O31.216 (3)
C12—C131.382 (4)N2—O41.219 (3)
C12—H120.9300N3—O61.214 (3)
C13—C141.387 (4)N3—O51.241 (3)
C13—H130.9300N4—N51.376 (3)
C14—H140.9300N4—H40.8600
C15—N91.349 (3)N6—O81.204 (3)
C15—C161.423 (3)N6—O71.205 (3)
C15—C201.413 (3)N7—O101.215 (3)
C16—C171.364 (3)N7—O91.224 (3)
C16—N61.473 (3)N8—O121.206 (3)
C17—C181.376 (3)N8—O111.236 (3)
C17—H170.9300N9—N101.366 (3)
C18—C191.368 (3)N9—H90.8600
Cl2···N7i3.430 (3)C27···N8i3.361 (4)
C25···C19i3.420 (4)N4···O2ii3.029 (3)
N4—C1—C2123.7 (2)C18—C19—H19120.6
N4—C1—C6121.8 (2)C20—C19—H19120.6
C2—C1—C6114.55 (19)C19—C20—C15123.0 (2)
C3—C2—C1123.7 (2)C19—C20—N8115.2 (2)
C3—C2—N1114.8 (2)C15—C20—N8121.8 (2)
C1—C2—N1121.21 (19)C22—C21—H21A109.5
C2—C3—C4118.6 (2)C22—C21—H21B109.5
C2—C3—H3120.7H21A—C21—H21B109.5
C4—C3—H3120.7C22—C21—H21C109.5
C5—C4—C3121.5 (2)H21A—C21—H21C109.5
C5—C4—N2119.4 (2)H21B—C21—H21C109.5
C3—C4—N2119.0 (2)N10—C22—C23116.0 (2)
C4—C5—C6119.4 (2)N10—C22—C21123.7 (2)
C4—C5—H5120.3C23—C22—C21120.2 (2)
C6—C5—H5120.3C24—C23—C28118.2 (2)
C5—C6—C1122.0 (2)C24—C23—C22120.3 (2)
C5—C6—N3115.7 (2)C28—C23—C22121.4 (2)
C1—C6—N3122.20 (19)C25—C24—C23120.1 (3)
C8—C7—H7A109.5C25—C24—H24120.0
C8—C7—H7B109.5C23—C24—H24120.0
H7A—C7—H7B109.5C26—C25—C24121.8 (2)
C8—C7—H7C109.5C26—C25—Cl2119.4 (2)
H7A—C7—H7C109.5C24—C25—Cl2118.8 (2)
H7B—C7—H7C109.5C25—C26—C27118.7 (3)
N5—C8—C9115.1 (2)C25—C26—H26120.7
N5—C8—C7123.2 (2)C27—C26—H26120.7
C9—C8—C7121.7 (2)C28—C27—C26120.7 (3)
C14—C9—C10118.4 (2)C28—C27—H27119.6
C14—C9—C8121.1 (2)C26—C27—H27119.6
C10—C9—C8120.5 (2)C27—C28—C23120.5 (2)
C11—C10—C9119.7 (2)C27—C28—H28119.8
C11—C10—H10120.1C23—C28—H28119.8
C9—C10—H10120.1O1—N1—O2125.1 (2)
C12—C11—C10122.3 (2)O1—N1—C2116.9 (2)
C12—C11—Cl1119.4 (2)O2—N1—C2117.9 (2)
C10—C11—Cl1118.3 (2)O3—N2—O4124.2 (2)
C11—C12—C13118.3 (3)O3—N2—C4117.8 (2)
C11—C12—H12120.8O4—N2—C4118.0 (2)
C13—C12—H12120.8O6—N3—O5122.2 (2)
C12—C13—C14120.9 (3)O6—N3—C6119.1 (2)
C12—C13—H13119.5O5—N3—C6118.7 (2)
C14—C13—H13119.5C1—N4—N5121.3 (2)
C13—C14—C9120.3 (2)C1—N4—H4119.3
C13—C14—H14119.8N5—N4—H4119.3
C9—C14—H14119.8C8—N5—N4114.8 (2)
N9—C15—C20122.2 (2)O8—N6—O7123.6 (2)
N9—C15—C16123.5 (2)O8—N6—C16117.7 (2)
C20—C15—C16114.3 (2)O7—N6—C16118.5 (2)
C17—C16—C15123.1 (2)O10—N7—O9124.4 (2)
C17—C16—N6114.7 (2)O10—N7—C18118.3 (2)
C15—C16—N6122.0 (2)O9—N7—C18117.3 (2)
C16—C17—C18119.1 (2)O12—N8—O11122.4 (2)
C16—C17—H17120.4O12—N8—C20118.9 (2)
C18—C17—H17120.4O11—N8—C20118.7 (2)
C19—C18—C17121.5 (2)C15—N9—N10122.7 (2)
C19—C18—N7119.0 (2)C15—N9—H9118.7
C17—C18—N7119.5 (2)N10—N9—H9118.7
C18—C19—C20118.9 (2)C22—N10—N9115.5 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+3/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O50.861.952.590 (3)130
N9—H9···O110.861.942.590 (3)131
 

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