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In the title mol­ecule, C19H15N7, the dihedral angle between the two benzotriazole moieties is 72.49 (6)° and those between the pyridine and the two benzotriazole moieties are 70.26 (6) and 57.70 (7)°. The crystal structure is stabilized by intermolecular C—H...N and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017567/ci6166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017567/ci6166Isup2.hkl
Contains datablock I

CCDC reference: 200747

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.100
  • Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2,6-Bis(N,N'-benzotriazol-1-ylmethyl)pyridine top
Crystal data top
C19H15N7F(000) = 712
Mr = 341.38Dx = 1.377 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 14.5526 (12) Åθ = 19.7–28.2°
b = 7.9438 (9) ŵ = 0.09 mm1
c = 14.2666 (8) ÅT = 298 K
β = 93.480 (6)°Block, colourless
V = 1646.2 (2) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 1717
ω–2θ scansk = 09
3025 measured reflectionsl = 016
2901 independent reflections3 standard reflections every 100 reflections
2104 reflections with I > 2σ(I) intensity decay: none
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2138P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2901 reflectionsΔρmax = 0.14 e Å3
236 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0058 (9)
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
N10.31396 (8)0.18574 (16)0.34202 (8)0.0395 (3)
N20.59335 (11)0.4266 (2)0.29172 (12)0.0647 (4)
N30.53300 (10)0.4351 (2)0.35576 (11)0.0609 (4)
N40.50281 (8)0.27785 (18)0.37372 (9)0.0452 (3)
N50.15538 (10)0.3414 (2)0.01910 (10)0.0572 (4)
N60.13086 (9)0.26556 (19)0.09427 (10)0.0524 (4)
N70.20714 (8)0.21196 (16)0.14464 (9)0.0420 (3)
C10.22398 (10)0.18759 (19)0.31806 (10)0.0398 (4)
C20.16004 (11)0.2606 (2)0.37278 (11)0.0502 (4)
H20.09770.25830.35420.060*
C30.19040 (11)0.3371 (2)0.45555 (12)0.0542 (5)
H30.14890.38790.49370.065*
C40.28293 (11)0.3371 (2)0.48092 (11)0.0463 (4)
H40.30500.38810.53650.056*
C50.34269 (10)0.26032 (19)0.42261 (10)0.0390 (4)
C60.44344 (11)0.2494 (2)0.45017 (11)0.0510 (4)
H6A0.45820.33170.49900.061*
H6B0.45650.13880.47650.061*
C70.60389 (11)0.2602 (2)0.26876 (11)0.0463 (4)
C80.54604 (10)0.1638 (2)0.32077 (10)0.0400 (4)
C90.54173 (11)0.0105 (2)0.31385 (11)0.0503 (4)
H90.50180.07380.34820.060*
C100.59956 (13)0.0836 (2)0.25369 (12)0.0579 (5)
H100.59900.20000.24690.069*
C110.65981 (12)0.0124 (3)0.20173 (12)0.0591 (5)
H110.69860.04220.16210.071*
C120.66269 (12)0.1827 (3)0.20804 (12)0.0573 (5)
H120.70240.24570.17320.069*
C130.19628 (12)0.1042 (2)0.22585 (11)0.0494 (4)
H13A0.23320.00360.21960.059*
H13B0.13240.06960.22640.059*
C140.24949 (12)0.3355 (2)0.01881 (11)0.0468 (4)
C150.28371 (10)0.25378 (19)0.09966 (10)0.0417 (4)
C160.37750 (12)0.2283 (2)0.11894 (14)0.0583 (5)
H160.40040.17550.17360.070*
C170.43400 (14)0.2854 (3)0.05292 (16)0.0731 (6)
H170.49720.27080.06310.088*
C180.39997 (16)0.3654 (3)0.02983 (15)0.0735 (6)
H180.44110.40110.07310.088*
C190.30849 (15)0.3917 (2)0.04813 (13)0.0635 (5)
H190.28610.44490.10290.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0399 (7)0.0395 (8)0.0389 (7)0.0048 (6)0.0007 (6)0.0010 (6)
N20.0602 (10)0.0529 (10)0.0828 (11)0.0024 (8)0.0185 (9)0.0020 (8)
N30.0537 (9)0.0551 (10)0.0745 (10)0.0032 (7)0.0082 (8)0.0037 (8)
N40.0340 (7)0.0564 (9)0.0449 (7)0.0033 (6)0.0006 (6)0.0009 (7)
N50.0567 (9)0.0622 (10)0.0506 (8)0.0045 (8)0.0146 (7)0.0007 (8)
N60.0415 (8)0.0599 (9)0.0540 (8)0.0055 (7)0.0122 (6)0.0064 (8)
N70.0380 (7)0.0464 (8)0.0404 (7)0.0006 (6)0.0078 (6)0.0032 (6)
C10.0413 (9)0.0360 (9)0.0420 (8)0.0034 (7)0.0003 (7)0.0067 (7)
C20.0333 (8)0.0653 (12)0.0522 (10)0.0014 (8)0.0041 (7)0.0077 (9)
C30.0469 (10)0.0700 (12)0.0468 (10)0.0091 (9)0.0130 (8)0.0002 (9)
C40.0463 (9)0.0569 (10)0.0360 (8)0.0023 (8)0.0048 (7)0.0010 (8)
C50.0396 (8)0.0427 (9)0.0346 (8)0.0028 (7)0.0015 (6)0.0043 (7)
C60.0407 (9)0.0745 (12)0.0374 (8)0.0076 (8)0.0007 (7)0.0029 (8)
C70.0397 (9)0.0504 (10)0.0485 (9)0.0027 (8)0.0016 (7)0.0027 (8)
C80.0318 (8)0.0521 (10)0.0353 (8)0.0015 (7)0.0046 (6)0.0002 (7)
C90.0514 (10)0.0551 (11)0.0444 (9)0.0077 (8)0.0019 (8)0.0034 (8)
C100.0687 (12)0.0514 (11)0.0535 (11)0.0007 (9)0.0032 (9)0.0045 (9)
C110.0584 (11)0.0699 (13)0.0502 (10)0.0076 (10)0.0126 (8)0.0051 (9)
C120.0500 (10)0.0668 (13)0.0564 (11)0.0043 (9)0.0137 (8)0.0033 (9)
C130.0524 (10)0.0440 (10)0.0510 (10)0.0108 (8)0.0040 (8)0.0008 (8)
C140.0552 (10)0.0433 (9)0.0406 (9)0.0013 (8)0.0076 (7)0.0074 (7)
C150.0411 (8)0.0400 (9)0.0431 (8)0.0012 (7)0.0045 (7)0.0055 (7)
C160.0422 (9)0.0641 (12)0.0675 (11)0.0003 (9)0.0066 (8)0.0026 (10)
C170.0473 (11)0.0816 (15)0.0910 (15)0.0068 (10)0.0085 (11)0.0046 (13)
C180.0772 (15)0.0758 (15)0.0695 (13)0.0213 (12)0.0208 (11)0.0101 (12)
C190.0866 (15)0.0559 (12)0.0473 (10)0.0134 (10)0.0011 (10)0.0029 (9)
Geometric parameters (Å, º) top
N1—C11.3332 (19)C7—C81.386 (2)
N1—C51.3377 (19)C7—C121.397 (2)
N2—N31.307 (2)C8—C91.389 (2)
N2—C71.373 (2)C9—C101.368 (2)
N3—N41.354 (2)C9—H90.93
N4—C81.358 (2)C10—C111.406 (3)
N4—C61.4496 (19)C10—H100.93
N5—N61.299 (2)C11—C121.357 (3)
N5—C141.371 (2)C11—H110.93
N6—N71.3538 (18)C12—H120.93
N7—C151.3603 (19)C13—H13A0.97
N7—C131.457 (2)C13—H13B0.97
C1—C21.378 (2)C14—C151.389 (2)
C1—C131.506 (2)C14—C191.396 (2)
C2—C31.377 (2)C15—C161.391 (2)
C2—H20.93C16—C171.365 (3)
C3—C41.373 (2)C16—H160.93
C3—H30.93C17—C181.404 (3)
C4—C51.382 (2)C17—H170.93
C4—H40.93C18—C191.357 (3)
C5—C61.497 (2)C18—H180.93
C6—H6A0.97C19—H190.93
C6—H6B0.97
C1—N1—C5117.80 (13)C7—C8—C9122.59 (15)
N3—N2—C7107.83 (14)C10—C9—C8116.17 (16)
N2—N3—N4108.90 (14)C10—C9—H9121.9
N3—N4—C8110.1 (1)C8—C9—H9121.9
N3—N4—C6120.1 (1)C9—C10—C11121.85 (18)
C8—N4—C6129.2 (2)C9—C10—H10119.1
N6—N5—C14108.13 (13)C11—C10—H10119.1
N5—N6—N7109.07 (13)C12—C11—C10121.56 (17)
N6—N7—C15110.0 (1)C12—C11—H11119.2
N6—N7—C13118.8 (1)C10—C11—H11119.2
C15—N7—C13130.6 (1)C11—C12—C7117.56 (17)
N1—C1—C2123.08 (14)C11—C12—H12121.2
N1—C1—C13115.19 (14)C7—C12—H12121.2
C2—C1—C13121.73 (14)N7—C13—C1113.57 (12)
C3—C2—C1118.62 (15)N7—C13—H13A108.9
C3—C2—H2120.7C1—C13—H13A108.9
C1—C2—H2120.7N7—C13—H13B108.9
C4—C3—C2119.00 (15)C1—C13—H13B108.9
C4—C3—H3120.5H13A—C13—H13B107.7
C2—C3—H3120.5N5—C14—C15108.75 (15)
C3—C4—C5118.96 (15)N5—C14—C19130.34 (16)
C3—C4—H4120.5C15—C14—C19120.88 (16)
C5—C4—H4120.5N7—C15—C14104.07 (13)
N1—C5—C4122.53 (14)N7—C15—C16133.91 (15)
N1—C5—C6116.76 (13)C14—C15—C16122.02 (16)
C4—C5—C6120.64 (14)C17—C16—C15116.13 (17)
N4—C6—C5114.35 (13)C17—C16—H16121.9
N4—C6—H6A108.7C15—C16—H16121.9
C5—C6—H6A108.7C16—C17—C18122.28 (19)
N4—C6—H6B108.7C16—C17—H17118.9
C5—C6—H6B108.7C18—C17—H17118.9
H6A—C6—H6B107.6C19—C18—C17121.54 (19)
N2—C7—C8108.89 (14)C19—C18—H18119.2
N2—C7—C12130.80 (16)C17—C18—H18119.2
C8—C7—C12120.25 (16)C18—C19—C14117.13 (18)
N4—C8—C7104.26 (14)C18—C19—H19121.4
N4—C8—C9133.14 (15)C14—C19—H19121.4
C7—N2—N3—N41.10 (19)C12—C7—C8—C91.6 (2)
N2—N3—N4—C81.00 (18)N4—C8—C9—C10177.56 (15)
N2—N3—N4—C6172.69 (14)C7—C8—C9—C101.3 (2)
C14—N5—N6—N71.04 (18)C8—C9—C10—C110.1 (2)
N5—N6—N7—C150.53 (18)C9—C10—C11—C120.8 (3)
N5—N6—N7—C13172.11 (13)C10—C11—C12—C70.4 (3)
C5—N1—C1—C20.8 (2)N2—C7—C12—C11177.83 (18)
C5—N1—C1—C13179.01 (13)C8—C7—C12—C110.7 (2)
N1—C1—C2—C30.8 (2)N6—N7—C13—C1111.93 (15)
C13—C1—C2—C3178.96 (15)C15—N7—C13—C178.5 (2)
C1—C2—C3—C40.4 (3)N1—C1—C13—N782.23 (17)
C2—C3—C4—C50.1 (3)C2—C1—C13—N797.54 (18)
C1—N1—C5—C40.3 (2)N6—N5—C14—C151.17 (19)
C1—N1—C5—C6177.19 (14)N6—N5—C14—C19176.73 (17)
C3—C4—C5—N10.1 (2)N6—N7—C15—C140.20 (17)
C3—C4—C5—C6176.68 (16)C13—N7—C15—C14170.09 (14)
N3—N4—C6—C591.04 (18)N6—N7—C15—C16179.11 (18)
C8—N4—C6—C599.05 (17)C13—N7—C15—C168.8 (3)
N1—C5—C6—N443.1 (2)N5—C14—C15—N70.82 (17)
C4—C5—C6—N4139.94 (16)C19—C14—C15—N7177.31 (15)
N3—N2—C7—C80.81 (19)N5—C14—C15—C16179.89 (15)
N3—N2—C7—C12176.56 (17)C19—C14—C15—C161.8 (2)
N3—N4—C8—C70.47 (16)N7—C15—C16—C17177.54 (18)
C6—N4—C8—C7171.18 (14)C14—C15—C16—C171.2 (3)
N3—N4—C8—C9178.50 (16)C15—C16—C17—C180.0 (3)
C6—N4—C8—C97.8 (3)C16—C17—C18—C190.7 (3)
N2—C7—C8—N40.20 (17)C17—C18—C19—C140.1 (3)
C12—C7—C8—N4177.50 (14)N5—C14—C19—C18178.7 (2)
N2—C7—C8—C9179.31 (15)C15—C14—C19—C181.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N10.932.783.385 (2)124
C6—H6A···N3i0.972.783.734 (2)170
C13—H13B···N3ii0.972.823.718 (2)154
C9—H9···N6ii0.932.493.405 (2)166
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y1/2, z+1/2.
 

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