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The title compound, C16H9N5, crystallized as thin needles from a 1:1 methanol solution of aniline and 1,2,4,5-tetra­cyano­benzene. Various kinds of short intermolecular contacts link the mol­ecules together in chains along the needle axis. Some of these contacts seem difficult to explain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000442/bt6100sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000442/bt6100Isup2.hkl
Contains datablock I

CCDC reference: 180786

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.138
  • Data-to-parameter ratio = 16.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(5) - C(51) = 1.44 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(6) - C(61) = 1.44 Ang. PLAT_420 Alert C D-H Without Acceptor N(31) - H(32) ? General Notes
ABSTY_01 Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998).

3-amino-5,6-dicyano-1-phenylimino-1H-isoindole top
Crystal data top
C16H9N5F(000) = 560
Mr = 271.28Dx = 1.404 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 11.571 (3) Åθ = 4.2–12.1°
b = 7.180 (3) ŵ = 0.09 mm1
c = 15.530 (5) ÅT = 100 K
β = 95.94 (4)°Needle, orange-brown
V = 1283.3 (8) Å30.60 × 0.15 × 0.15 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
1542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.0°, θmin = 2.1°
ω–2θ scansh = 115
Absorption correction: gaussian (PLATON; Spek, 1998)k = 19
Tmin = 0.986, Tmax = 0.988l = 2020
4052 measured reflections2 standard reflections every 60 min
3047 independent reflections intensity decay: 1%
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0642P)2]
where P = (Fo2 + 2Fc2)/3
3047 reflections(Δ/σ)max = 0.003
190 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 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
C10.60957 (18)0.3521 (3)0.61030 (14)0.0177 (5)
N20.56699 (16)0.2022 (3)0.55738 (12)0.0200 (5)
C30.58642 (18)0.2440 (3)0.47718 (14)0.0176 (5)
C40.67631 (19)0.5274 (4)0.40201 (14)0.0202 (5)
H40.66560.48020.34460.024*
C50.7272 (2)0.7004 (4)0.42049 (14)0.0201 (5)
C60.74558 (19)0.7670 (4)0.50646 (14)0.0196 (5)
C70.70889 (19)0.6644 (3)0.57438 (14)0.0185 (5)
H70.71970.70940.63220.022*
C80.65656 (19)0.4960 (3)0.55522 (14)0.0178 (5)
C90.64222 (19)0.4280 (3)0.47074 (14)0.0172 (5)
N110.60866 (16)0.3733 (3)0.69207 (11)0.0184 (4)
C110.57355 (19)0.2285 (4)0.74474 (14)0.0190 (5)
C120.5054 (2)0.2741 (4)0.81072 (14)0.0240 (6)
H120.47950.39860.81620.029*
C130.4751 (2)0.1396 (4)0.86822 (16)0.0288 (6)
H130.42660.17160.91170.035*
C140.5151 (2)0.0409 (4)0.86263 (16)0.0293 (6)
H140.49490.13260.90250.035*
C150.5849 (2)0.0875 (4)0.79844 (15)0.0255 (6)
H150.61280.21130.79460.031*
C160.6142 (2)0.0457 (4)0.73990 (15)0.0219 (6)
H160.66210.01270.69620.026*
N310.55870 (17)0.1348 (3)0.40965 (12)0.0217 (5)
H310.52510.02660.41660.026*
H320.57380.17020.35770.026*
C510.7628 (2)0.8109 (4)0.35032 (16)0.0281 (6)
N510.7905 (2)0.8966 (4)0.29423 (14)0.0437 (7)
C610.8023 (2)0.9445 (4)0.52257 (15)0.0218 (5)
N610.84824 (19)1.0837 (3)0.53409 (14)0.0305 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0130 (11)0.0176 (12)0.0218 (11)0.0000 (9)0.0012 (8)0.0028 (10)
N20.0188 (10)0.0212 (11)0.0200 (10)0.0010 (9)0.0016 (8)0.0031 (9)
C30.0123 (10)0.0194 (13)0.0203 (11)0.0024 (10)0.0015 (8)0.0007 (10)
C40.0163 (11)0.0282 (14)0.0158 (11)0.0027 (10)0.0000 (8)0.0037 (11)
C50.0160 (11)0.0255 (13)0.0187 (11)0.0003 (10)0.0017 (9)0.0039 (11)
C60.0151 (10)0.0211 (13)0.0221 (12)0.0005 (10)0.0008 (9)0.0026 (10)
C70.0170 (11)0.0215 (13)0.0164 (11)0.0022 (10)0.0016 (8)0.0003 (10)
C80.0144 (11)0.0215 (13)0.0173 (11)0.0008 (10)0.0006 (8)0.0025 (11)
C90.0132 (11)0.0199 (13)0.0182 (11)0.0004 (10)0.0001 (8)0.0011 (10)
N110.0164 (10)0.0201 (11)0.0182 (10)0.0013 (9)0.0003 (7)0.0015 (9)
C110.0167 (11)0.0236 (13)0.0156 (11)0.0035 (10)0.0037 (8)0.0016 (10)
C120.0200 (12)0.0292 (15)0.0226 (12)0.0034 (11)0.0016 (9)0.0012 (11)
C130.0227 (13)0.0401 (17)0.0246 (13)0.0013 (13)0.0064 (10)0.0044 (13)
C140.0216 (13)0.0389 (17)0.0270 (13)0.0054 (12)0.0002 (10)0.0107 (13)
C150.0282 (14)0.0215 (14)0.0250 (13)0.0008 (11)0.0048 (10)0.0024 (11)
C160.0209 (12)0.0246 (14)0.0198 (11)0.0004 (11)0.0005 (9)0.0009 (10)
N310.0258 (11)0.0209 (11)0.0184 (9)0.0044 (9)0.0017 (8)0.0034 (9)
C510.0279 (13)0.0346 (16)0.0218 (12)0.0090 (12)0.0016 (10)0.0001 (12)
N510.0507 (15)0.0561 (18)0.0234 (12)0.0256 (14)0.0005 (10)0.0085 (13)
C610.0248 (13)0.0221 (14)0.0184 (11)0.0006 (11)0.0018 (9)0.0030 (11)
N610.0304 (12)0.0261 (13)0.0342 (12)0.0077 (11)0.0009 (9)0.0003 (10)
Geometric parameters (Å, º) top
C1—N111.280 (3)N11—C111.409 (3)
C1—N21.411 (3)C11—C121.395 (3)
C1—C81.481 (3)C11—C161.398 (4)
N2—C31.323 (3)C12—C131.384 (3)
C3—N311.322 (3)C12—H120.9500
C3—C91.478 (3)C13—C141.382 (4)
C4—C51.391 (4)C13—H130.9500
C4—C91.375 (3)C14—C151.387 (3)
C4—H40.9500C14—H140.9500
C5—C511.443 (3)C15—C161.385 (3)
C5—C61.413 (3)C15—H150.9500
C6—C71.388 (3)C16—H160.9500
C6—C611.443 (4)N31—H310.8800
C7—C81.371 (3)N31—H320.8800
C7—H70.9500C51—N511.139 (3)
C8—C91.394 (3)C61—N611.137 (3)
N11—C1—N2129.1 (2)C1—N11—C11121.4 (2)
N11—C1—C8122.1 (2)C12—C11—N11118.2 (2)
N2—C1—C8108.83 (18)C12—C11—C16118.6 (2)
C3—N2—C1107.0 (2)N11—C11—C16122.9 (2)
N31—C3—N2124.2 (2)C11—C12—C13120.7 (2)
N31—C3—C9123.2 (2)C11—C12—H12119.7
N2—C3—C9112.6 (2)C13—C12—H12119.7
C5—C4—C9116.9 (2)C14—C13—C12120.3 (2)
C5—C4—H4121.6C14—C13—H13119.8
C9—C4—H4121.6C12—C13—H13119.8
C4—C5—C51118.9 (2)C13—C14—C15119.7 (2)
C4—C5—C6121.1 (2)C13—C14—H14120.2
C51—C5—C6120.0 (2)C15—C14—H14120.2
C7—C6—C5120.7 (2)C16—C15—C14120.3 (3)
C7—C6—C61120.4 (2)C16—C15—H15119.8
C5—C6—C61118.9 (2)C14—C15—H15119.8
C6—C7—C8117.8 (2)C15—C16—C11120.4 (2)
C6—C7—H7121.1C15—C16—H16119.8
C8—C7—H7121.1C11—C16—H16119.8
C9—C8—C7121.3 (2)C3—N31—H31120.0
C9—C8—C1106.5 (2)C3—N31—H32120.0
C7—C8—C1132.1 (2)H31—N31—H32120.0
C4—C9—C8122.2 (2)N51—C51—C5179.2 (3)
C4—C9—C3132.7 (2)N61—C61—C6178.8 (3)
C8—C9—C3105.06 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N31—H31···N2i0.882.022.896 (3)172
C4—H4···N51ii0.952.343.250 (3)159
C12—H12···N51iii0.952.633.422 (4)141
Symmetry codes: (i) x+1, y, z+1; (ii) x+3/2, y1/2, z+1/2; (iii) x1/2, y+3/2, z+1/2.
 

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