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In the title compound, C17H11N3, the dihedral angle between the tolyl and tricyano­phenyl rings is 81.1 (1)°. The crystal structure is stabilized by weak C—H...N hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005387/om2090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005387/om2090Isup2.hkl
Contains datablock I

CCDC reference: 640431

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.048
  • wR factor = 0.144
  • Data-to-parameter ratio = 55.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C16 .. 8.81 su
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.647 Test value = 0.525 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.38 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.65 e/A    PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C14 .. 6.93 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C15 .. 6.97 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C14 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C15 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C16 ... 1.44 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. N1 .. 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. N3 .. 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. N3 .. 2.73 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

5-[(4-Methylphenyl)methyl]benzene-1,2,4-tricarbonitrile top
Crystal data top
C17H11N3F(000) = 536
Mr = 257.29Dx = 1.250 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7132 reflections
a = 9.5455 (2) Åθ = 2.6–42.9°
b = 9.3500 (2) ŵ = 0.08 mm1
c = 15.3899 (3) ÅT = 100 K
β = 95.617 (1)°Block, colourless
V = 1366.96 (5) Å30.52 × 0.46 × 0.40 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD
diffractometer
10008 independent reflections
Radiation source: fine-focus sealed tube8050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.33 pixels mm-1θmax = 42.9°, θmin = 2.6°
ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1717
Tmin = 0.879, Tmax = 0.970l = 2929
63196 measured 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) = 0.144H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0794P)2 + 0.1393P]
where P = (Fo2 + 2Fc2)/3
10008 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.27 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
N10.08435 (7)0.34089 (7)0.10877 (3)0.02678 (11)
N20.12630 (7)0.34589 (7)0.32472 (4)0.02850 (11)
N30.34813 (7)0.13509 (7)0.52048 (4)0.02784 (11)
C10.29525 (5)0.11150 (5)0.24395 (3)0.01454 (7)
H1A0.34480.11390.19480.017*
C20.17471 (5)0.19473 (5)0.24606 (3)0.01433 (7)
C30.09958 (5)0.19430 (5)0.32037 (3)0.01517 (8)
C40.14550 (5)0.10894 (5)0.39165 (3)0.01600 (8)
H4A0.09690.10790.44120.019*
C50.26567 (5)0.02491 (5)0.38764 (3)0.01478 (7)
C60.34283 (5)0.02464 (5)0.31429 (3)0.01383 (7)
C70.47004 (6)0.07117 (6)0.31260 (3)0.01775 (8)
H7A0.53140.05600.36590.021*
H7B0.43890.16990.31240.021*
C80.55428 (5)0.04844 (5)0.23566 (3)0.01571 (8)
C90.67006 (6)0.04341 (6)0.24210 (3)0.01819 (8)
H9A0.69540.09170.29410.022*
C100.74809 (6)0.06313 (6)0.17081 (4)0.02021 (9)
H10A0.82490.12480.17600.024*
C110.71276 (6)0.00812 (6)0.09196 (3)0.01905 (9)
C120.59584 (6)0.09902 (6)0.08589 (3)0.01906 (9)
H12A0.57010.14700.03380.023*
C130.51742 (6)0.11879 (6)0.15662 (3)0.01751 (8)
H13A0.43980.17940.15120.021*
C140.12501 (6)0.27750 (6)0.17064 (3)0.01823 (9)
C150.02479 (6)0.27968 (6)0.32299 (3)0.01950 (9)
C160.31064 (6)0.06405 (6)0.46124 (3)0.01909 (9)
C170.79813 (7)0.01157 (8)0.01580 (4)0.02758 (12)
H17A0.74080.05520.03170.041*
H17B0.83060.07980.00240.041*
H17C0.87750.07190.03280.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0332 (3)0.0302 (3)0.01669 (18)0.0095 (2)0.00146 (17)0.00585 (17)
N20.0282 (3)0.0325 (3)0.0254 (2)0.0125 (2)0.00543 (18)0.00241 (19)
N30.0375 (3)0.0266 (2)0.0191 (2)0.0047 (2)0.00117 (18)0.00810 (17)
C10.01590 (17)0.01502 (17)0.01276 (15)0.00052 (13)0.00168 (12)0.00103 (12)
C20.01625 (17)0.01453 (16)0.01208 (15)0.00058 (13)0.00071 (12)0.00069 (12)
C30.01618 (18)0.01581 (17)0.01358 (16)0.00150 (13)0.00171 (12)0.00013 (13)
C40.01843 (19)0.01653 (18)0.01334 (16)0.00063 (14)0.00306 (13)0.00080 (13)
C50.01774 (18)0.01428 (16)0.01224 (15)0.00026 (13)0.00100 (12)0.00152 (12)
C60.01516 (17)0.01352 (16)0.01270 (15)0.00032 (13)0.00081 (12)0.00029 (12)
C70.01842 (19)0.01812 (19)0.01689 (18)0.00377 (15)0.00270 (14)0.00291 (14)
C80.01553 (17)0.01567 (17)0.01584 (17)0.00238 (13)0.00107 (13)0.00024 (13)
C90.01756 (19)0.01852 (19)0.01848 (18)0.00011 (15)0.00171 (14)0.00343 (15)
C100.01717 (19)0.0222 (2)0.0216 (2)0.00153 (16)0.00372 (15)0.00225 (16)
C110.0179 (2)0.0217 (2)0.01790 (19)0.00398 (16)0.00347 (15)0.00026 (15)
C120.0202 (2)0.0208 (2)0.01587 (18)0.00249 (16)0.00027 (14)0.00184 (15)
C130.01762 (19)0.01770 (19)0.01689 (18)0.00016 (15)0.00003 (14)0.00100 (14)
C140.0207 (2)0.0197 (2)0.01420 (17)0.00401 (16)0.00127 (14)0.00185 (14)
C150.0208 (2)0.0215 (2)0.01636 (18)0.00446 (16)0.00297 (15)0.00034 (15)
C160.0237 (2)0.01866 (19)0.01486 (17)0.00147 (16)0.00172 (15)0.00302 (14)
C170.0252 (3)0.0364 (3)0.0225 (2)0.0033 (2)0.00922 (19)0.0017 (2)
Geometric parameters (Å, º) top
N1—C141.1560 (7)C7—H7A0.9700
N2—C151.1523 (8)C7—H7B0.9700
N3—C161.1561 (7)C8—C91.3955 (7)
C1—C21.3921 (7)C8—C131.3973 (7)
C1—C61.3934 (6)C9—C101.3972 (8)
C1—H1A0.9300C9—H9A0.9300
C2—C31.4080 (7)C10—C111.3965 (8)
C2—C141.437 (1)C10—H10A0.9300
C3—C41.3922 (7)C11—C121.3986 (8)
C3—C151.435 (1)C11—C171.5029 (8)
C4—C51.3967 (7)C12—C131.3924 (8)
C4—H4A0.9300C12—H12A0.9300
C5—C61.4069 (7)C13—H13A0.9300
C5—C161.437 (1)C17—H17A0.9600
C6—C71.5113 (7)C17—H17B0.9600
C7—C81.5101 (7)C17—H17C0.9600
C2—C1—C6121.00 (4)C13—C8—C7120.56 (5)
C2—C1—H1A119.5C8—C9—C10120.32 (5)
C6—C1—H1A119.5C8—C9—H9A119.8
C1—C2—C3120.35 (4)C10—C9—H9A119.8
C1—C2—C14119.38 (4)C11—C10—C9121.16 (5)
C3—C2—C14120.24 (4)C11—C10—H10A119.4
C4—C3—C2119.70 (4)C9—C10—H10A119.4
C4—C3—C15119.64 (4)C10—C11—C12118.11 (5)
C2—C3—C15120.66 (4)C10—C11—C17121.07 (5)
C3—C4—C5118.97 (4)C12—C11—C17120.82 (5)
C3—C4—H4A120.5C13—C12—C11121.00 (5)
C5—C4—H4A120.5C13—C12—H12A119.5
C4—C5—C6122.22 (4)C11—C12—H12A119.5
C4—C5—C16118.31 (4)C12—C13—C8120.61 (5)
C6—C5—C16119.47 (4)C12—C13—H13A119.7
C1—C6—C5117.77 (4)C8—C13—H13A119.7
C1—C6—C7122.24 (4)N1—C14—C2178.24 (6)
C5—C6—C7119.97 (4)N2—C15—C3178.65 (7)
C8—C7—C6114.87 (4)N3—C16—C5179.34 (7)
C8—C7—H7A108.6C11—C17—H17A109.5
C6—C7—H7A108.6C11—C17—H17B109.5
C8—C7—H7B108.6H17A—C17—H17B109.5
C6—C7—H7B108.6C11—C17—H17C109.5
H7A—C7—H7B107.5H17A—C17—H17C109.5
C9—C8—C13118.79 (5)H17B—C17—H17C109.5
C9—C8—C7120.65 (4)
C6—C1—C2—C31.02 (7)C16—C5—C6—C71.33 (7)
C6—C1—C2—C14176.96 (5)C1—C6—C7—C89.22 (7)
C1—C2—C3—C40.68 (7)C5—C6—C7—C8172.69 (4)
C14—C2—C3—C4177.29 (5)C6—C7—C8—C993.80 (6)
C1—C2—C3—C15179.94 (5)C6—C7—C8—C1386.04 (6)
C14—C2—C3—C151.97 (7)C13—C8—C9—C100.61 (8)
C2—C3—C4—C50.14 (7)C7—C8—C9—C10179.55 (5)
C15—C3—C4—C5179.13 (5)C8—C9—C10—C110.12 (9)
C3—C4—C5—C60.65 (7)C9—C10—C11—C120.65 (8)
C3—C4—C5—C16179.18 (5)C9—C10—C11—C17179.08 (6)
C2—C1—C6—C50.52 (7)C10—C11—C12—C130.45 (8)
C2—C1—C6—C7177.61 (5)C17—C11—C12—C13179.27 (5)
C4—C5—C6—C10.32 (7)C11—C12—C13—C80.27 (8)
C16—C5—C6—C1179.51 (5)C9—C8—C13—C120.80 (8)
C4—C5—C6—C7178.49 (5)C7—C8—C13—C12179.36 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N1i0.932.643.480 (1)151
C7—H7A···N3ii0.972.683.530 (1)147
C13—H13A···N3iii0.932.733.411 (1)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x, y1/2, z1/2.
 

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