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The crystal structure of the title compound, C21H13N3, is stabilized by C—H...N, C—H...π and π...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000831/ci6095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000831/ci6095Isup2.hkl
Contains datablock I

CCDC reference: 180789

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.133
  • Data-to-parameter ratio = 14.6

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(1) - C(20) = 1.44 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(2) - C(21) = 1.44 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

3-[(diphenylmethylene)amino]phthalonitrile top
Crystal data top
C21H13N3Dx = 1.240 Mg m3
Mr = 307.34Melting point: 415 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.3572 (2) ÅCell parameters from 4600 reflections
b = 8.0212 (2) Åθ = 2.7–28.3°
c = 26.7363 (2) ŵ = 0.08 mm1
β = 91.648 (1)°T = 183 K
V = 3292.1 (1) Å3Slab, yellow
Z = 80.44 × 0.28 × 0.12 mm
F(000) = 1280
Data collection top
Siemens SMART CCD area-detector
diffractometer
3941 independent reflections
Radiation source: fine-focus sealed tube2251 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.7°
ω scansh = 2020
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.968, Tmax = 0.991l = 2535
9550 measured 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)] = 0.058All H-atom parameters refined
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0427P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max < 0.001
3941 reflectionsΔρmax = 0.32 e Å3
270 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (7)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
N10.22150 (9)0.84975 (19)0.10963 (6)0.0279 (4)
N20.19821 (13)0.4134 (2)0.08851 (7)0.0509 (5)
N30.08426 (13)0.3948 (2)0.04913 (7)0.0522 (5)
C10.15900 (11)0.6853 (2)0.04099 (6)0.0239 (4)
C20.11877 (11)0.6775 (2)0.00667 (7)0.0270 (4)
C30.09587 (13)0.8221 (3)0.03202 (8)0.0336 (5)
C40.11367 (13)0.9748 (3)0.00990 (8)0.0352 (5)
C50.15260 (12)0.9842 (3)0.03692 (8)0.0307 (5)
C60.17479 (11)0.8396 (2)0.06354 (7)0.0248 (4)
C70.18770 (11)0.9144 (2)0.14858 (7)0.0239 (4)
C80.09427 (11)0.9638 (2)0.15342 (6)0.0238 (4)
C90.02584 (11)0.8638 (2)0.13568 (7)0.0267 (4)
C100.05977 (12)0.9171 (3)0.14011 (7)0.0316 (5)
C110.07742 (13)1.0700 (3)0.16165 (7)0.0343 (5)
C120.00998 (13)1.1678 (3)0.17970 (8)0.0383 (5)
C130.07541 (13)1.1147 (2)0.17596 (8)0.0335 (5)
C140.24825 (11)0.9502 (2)0.19195 (7)0.0237 (4)
C150.33116 (11)1.0126 (2)0.18295 (7)0.0276 (4)
C160.38705 (12)1.0514 (3)0.22294 (8)0.0328 (5)
C170.36235 (13)1.0232 (3)0.27153 (8)0.0336 (5)
C180.28037 (13)0.9594 (2)0.28057 (8)0.0324 (5)
C190.22273 (12)0.9268 (2)0.24103 (7)0.0288 (4)
C200.18153 (13)0.5345 (2)0.06764 (7)0.0318 (5)
C210.10048 (13)0.5187 (3)0.02987 (7)0.0340 (5)
H90.0388 (11)0.753 (3)0.1199 (7)0.036 (5)*
H120.0211 (12)1.270 (3)0.1980 (8)0.050 (6)*
H160.4446 (13)1.096 (2)0.2162 (7)0.034 (5)*
H50.1656 (12)1.090 (2)0.0511 (7)0.035 (5)*
H30.0686 (12)0.815 (2)0.0653 (8)0.041 (6)*
H110.1394 (13)1.108 (3)0.1646 (7)0.045 (6)*
H190.1622 (13)0.880 (3)0.2479 (8)0.045 (6)*
H100.1055 (14)0.843 (3)0.1265 (8)0.050 (6)*
H130.1243 (13)1.186 (2)0.1899 (7)0.045 (6)*
H40.0990 (12)1.073 (3)0.0271 (8)0.038 (6)*
H180.2633 (12)0.943 (3)0.3170 (8)0.046 (6)*
H170.4025 (12)1.047 (2)0.3004 (8)0.039 (6)*
H150.3464 (12)1.032 (2)0.1471 (8)0.043 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0306 (8)0.0281 (9)0.0246 (9)0.0020 (6)0.0041 (7)0.0077 (7)
N20.0834 (15)0.0359 (11)0.0328 (11)0.0039 (10)0.0085 (10)0.0035 (9)
N30.0747 (14)0.0420 (12)0.0396 (11)0.0150 (10)0.0049 (10)0.0130 (9)
C10.0262 (9)0.0251 (10)0.0203 (9)0.0009 (7)0.0016 (7)0.0023 (7)
C20.0324 (10)0.0289 (11)0.0199 (10)0.0040 (8)0.0006 (8)0.0044 (8)
C30.0419 (11)0.0365 (12)0.0221 (11)0.0020 (9)0.0049 (9)0.0009 (9)
C40.0447 (12)0.0305 (12)0.0303 (12)0.0032 (9)0.0027 (9)0.0042 (9)
C50.0366 (11)0.0241 (11)0.0315 (11)0.0001 (8)0.0004 (9)0.0046 (9)
C60.0237 (9)0.0292 (10)0.0215 (10)0.0008 (7)0.0019 (7)0.0059 (8)
C70.0301 (9)0.0182 (9)0.0232 (10)0.0001 (7)0.0022 (8)0.0030 (7)
C80.0267 (9)0.0253 (10)0.0194 (9)0.0010 (7)0.0014 (7)0.0021 (7)
C90.0297 (10)0.0283 (11)0.0220 (10)0.0029 (8)0.0009 (8)0.0012 (8)
C100.0289 (10)0.0387 (12)0.0270 (11)0.0069 (8)0.0011 (8)0.0023 (9)
C110.0287 (10)0.0440 (13)0.0304 (11)0.0054 (9)0.0033 (9)0.0041 (9)
C120.0386 (11)0.0346 (13)0.0418 (13)0.0086 (9)0.0006 (10)0.0106 (10)
C130.0314 (10)0.0293 (11)0.0394 (12)0.0017 (8)0.0031 (9)0.0126 (9)
C140.0263 (9)0.0211 (10)0.0236 (10)0.0023 (7)0.0022 (8)0.0044 (7)
C150.0237 (9)0.0321 (11)0.0269 (11)0.0041 (7)0.0004 (8)0.0041 (8)
C160.0233 (10)0.0371 (12)0.0377 (12)0.0031 (8)0.0052 (9)0.0076 (9)
C170.0317 (11)0.0368 (12)0.0314 (12)0.0084 (8)0.0146 (9)0.0078 (9)
C180.0381 (11)0.0354 (12)0.0233 (11)0.0075 (9)0.0044 (9)0.0012 (9)
C190.0310 (10)0.0300 (11)0.0253 (11)0.0016 (8)0.0020 (8)0.0009 (8)
C200.0438 (11)0.0307 (12)0.0206 (10)0.0016 (9)0.0007 (9)0.0075 (9)
C210.0445 (12)0.0360 (12)0.0214 (10)0.0060 (9)0.0023 (9)0.0023 (9)
Geometric parameters (Å, º) top
N1—C71.286 (2)C9—H91.01 (2)
N1—C61.410 (2)C10—C111.385 (3)
N2—C201.146 (2)C10—H100.98 (2)
N3—C211.143 (2)C11—C121.376 (3)
C1—C61.395 (2)C11—H111.00 (2)
C1—C21.401 (2)C12—C131.385 (3)
C1—C201.441 (3)C12—H120.97 (2)
C2—C31.384 (3)C13—H131.01 (2)
C2—C211.441 (3)C14—C191.393 (2)
C3—C41.384 (3)C14—C151.395 (2)
C3—H30.97 (2)C15—C161.387 (3)
C4—C51.374 (3)C15—H151.01 (2)
C4—H40.94 (2)C16—C171.382 (3)
C5—C61.398 (3)C16—H160.975 (19)
C5—H50.947 (19)C17—C181.387 (3)
C7—C141.493 (2)C17—H170.99 (2)
C7—C81.498 (2)C18—C191.384 (3)
C8—C131.387 (3)C18—H181.02 (2)
C8—C91.394 (2)C19—H191.02 (2)
C9—C101.391 (3)
C7—N1—C6121.59 (15)C9—C10—H10116.7 (12)
C6—C1—C2119.96 (17)C12—C11—C10119.77 (19)
C6—C1—C20119.65 (16)C12—C11—H11120.4 (12)
C2—C1—C20120.35 (16)C10—C11—H11119.8 (12)
C3—C2—C1120.47 (17)C11—C12—C13120.3 (2)
C3—C2—C21119.11 (17)C11—C12—H12121.0 (12)
C1—C2—C21120.42 (17)C13—C12—H12118.5 (12)
C2—C3—C4119.21 (19)C12—C13—C8120.66 (18)
C2—C3—H3119.6 (12)C12—C13—H13119.6 (11)
C4—C3—H3121.2 (12)C8—C13—H13119.8 (11)
C5—C4—C3120.9 (2)C19—C14—C15119.57 (16)
C5—C4—H4119.5 (12)C19—C14—C7121.32 (16)
C3—C4—H4119.6 (12)C15—C14—C7119.09 (16)
C4—C5—C6120.79 (19)C16—C15—C14119.68 (18)
C4—C5—H5119.7 (12)C16—C15—H15123.0 (11)
C6—C5—H5119.5 (12)C14—C15—H15117.3 (11)
C1—C6—C5118.63 (17)C17—C16—C15120.48 (19)
C1—C6—N1120.44 (16)C17—C16—H16120.6 (12)
C5—C6—N1120.50 (16)C15—C16—H16118.9 (12)
N1—C7—C14116.72 (16)C16—C17—C18119.95 (18)
N1—C7—C8125.91 (16)C16—C17—H17121.2 (11)
C14—C7—C8117.30 (15)C18—C17—H17118.8 (11)
C13—C8—C9119.03 (17)C19—C18—C17120.02 (19)
C13—C8—C7118.77 (16)C19—C18—H18121.7 (11)
C9—C8—C7122.21 (16)C17—C18—H18118.3 (11)
C10—C9—C8119.95 (18)C18—C19—C14120.20 (18)
C10—C9—H9120.4 (10)C18—C19—H19119.7 (12)
C8—C9—H9119.6 (10)C14—C19—H19120.0 (12)
C11—C10—C9120.30 (18)N2—C20—C1178.9 (2)
C11—C10—H10122.9 (12)N3—C21—C2178.1 (2)
C6—C1—C2—C31.1 (3)C14—C7—C8—C9140.11 (17)
C20—C1—C2—C3179.01 (17)C13—C8—C9—C100.9 (3)
C6—C1—C2—C21178.68 (17)C7—C8—C9—C10178.58 (17)
C20—C1—C2—C210.8 (3)C8—C9—C10—C110.6 (3)
C1—C2—C3—C40.4 (3)C9—C10—C11—C121.4 (3)
C21—C2—C3—C4179.76 (18)C10—C11—C12—C130.7 (3)
C2—C3—C4—C50.8 (3)C11—C12—C13—C80.9 (3)
C3—C4—C5—C60.4 (3)C9—C8—C13—C121.7 (3)
C2—C1—C6—C52.3 (2)C7—C8—C13—C12177.83 (18)
C20—C1—C6—C5179.84 (17)N1—C7—C14—C19142.58 (18)
C2—C1—C6—N1174.82 (15)C8—C7—C14—C1940.1 (2)
C20—C1—C6—N17.3 (2)N1—C7—C14—C1539.2 (2)
C4—C5—C6—C11.9 (3)C8—C7—C14—C15138.12 (17)
C4—C5—C6—N1174.45 (18)C19—C14—C15—C160.3 (3)
C7—N1—C6—C1120.53 (19)C7—C14—C15—C16177.96 (16)
C7—N1—C6—C567.1 (2)C14—C15—C16—C172.3 (3)
C6—N1—C7—C14167.85 (16)C15—C16—C17—C181.5 (3)
C6—N1—C7—C89.2 (3)C16—C17—C18—C191.2 (3)
N1—C7—C8—C13136.6 (2)C17—C18—C19—C143.1 (3)
C14—C7—C8—C1340.4 (2)C15—C14—C19—C182.4 (3)
N1—C7—C8—C942.9 (3)C7—C14—C19—C18179.37 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···N2i1.02 (2)2.59 (2)3.526 (3)152 (1)
C3—H3···Cg(A)ii0.97 (2)3.03 (2)3.901 (2)150 (1)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y+2, z.
 

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