2,6-Bis(N,N′-benzotriazol-1-yl­methyl)­pyridine

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.

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

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Computing details

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

Crystal data

C19H15N7	F(000) = 712
Mr = 341.38	Dx = 1.377 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.5526 (12) Å	θ = 19.7–28.2°
b = 7.9438 (9) Å	µ = 0.09 mm^−1
c = 14.2666 (8) Å	T = 298 K
β = 93.480 (6)°	Block, colourless
V = 1646.2 (2) Å^3	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Enraf Nonius CAD-4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −17→17
ω–2θ scans	k = 0→9
3025 measured reflections	l = 0→16
2901 independent reflections	3 standard reflections every 100 reflections
2104 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.2138P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2901 reflections	Δρmax = 0.14 e Å^−3
236 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.31396 (8)	0.18574 (16)	0.34202 (8)	0.0395 (3)
N2	0.59335 (11)	0.4266 (2)	0.29172 (12)	0.0647 (4)
N3	0.53300 (10)	0.4351 (2)	0.35576 (11)	0.0609 (4)
N4	0.50281 (8)	0.27785 (18)	0.37372 (9)	0.0452 (3)
N5	0.15538 (10)	0.3414 (2)	0.01910 (10)	0.0572 (4)
N6	0.13086 (9)	0.26556 (19)	0.09427 (10)	0.0524 (4)
N7	0.20714 (8)	0.21196 (16)	0.14464 (9)	0.0420 (3)
C1	0.22398 (10)	0.18759 (19)	0.31806 (10)	0.0398 (4)
C2	0.16004 (11)	0.2606 (2)	0.37278 (11)	0.0502 (4)
H2	0.0977	0.2583	0.3542	0.060*
C3	0.19040 (11)	0.3371 (2)	0.45555 (12)	0.0542 (5)
H3	0.1489	0.3879	0.4937	0.065*
C4	0.28293 (11)	0.3371 (2)	0.48092 (11)	0.0463 (4)
H4	0.3050	0.3881	0.5365	0.056*
C5	0.34269 (10)	0.26032 (19)	0.42261 (10)	0.0390 (4)
C6	0.44344 (11)	0.2494 (2)	0.45017 (11)	0.0510 (4)
H6A	0.4582	0.3317	0.4990	0.061*
H6B	0.4565	0.1388	0.4765	0.061*
C7	0.60389 (11)	0.2602 (2)	0.26876 (11)	0.0463 (4)
C8	0.54604 (10)	0.1638 (2)	0.32077 (10)	0.0400 (4)
C9	0.54173 (11)	−0.0105 (2)	0.31385 (11)	0.0503 (4)
H9	0.5018	−0.0738	0.3482	0.060*
C10	0.59956 (13)	−0.0836 (2)	0.25369 (12)	0.0579 (5)
H10	0.5990	−0.2000	0.2469	0.069*
C11	0.65981 (12)	0.0124 (3)	0.20173 (12)	0.0591 (5)
H11	0.6986	−0.0422	0.1621	0.071*
C12	0.66269 (12)	0.1827 (3)	0.20804 (12)	0.0573 (5)
H12	0.7024	0.2457	0.1732	0.069*
C13	0.19628 (12)	0.1042 (2)	0.22585 (11)	0.0494 (4)
H13A	0.2332	0.0036	0.2196	0.059*
H13B	0.1324	0.0696	0.2264	0.059*
C14	0.24949 (12)	0.3355 (2)	0.01881 (11)	0.0468 (4)
C15	0.28371 (10)	0.25378 (19)	0.09966 (10)	0.0417 (4)
C16	0.37750 (12)	0.2283 (2)	0.11894 (14)	0.0583 (5)
H16	0.4004	0.1755	0.1736	0.070*
C17	0.43400 (14)	0.2854 (3)	0.05292 (16)	0.0731 (6)
H17	0.4972	0.2708	0.0631	0.088*
C18	0.39997 (16)	0.3654 (3)	−0.02983 (15)	0.0735 (6)
H18	0.4411	0.4011	−0.0731	0.088*
C19	0.30849 (15)	0.3917 (2)	−0.04813 (13)	0.0635 (5)
H19	0.2861	0.4449	−0.1029	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0399 (7)	0.0395 (8)	0.0389 (7)	0.0048 (6)	−0.0007 (6)	0.0010 (6)
N2	0.0602 (10)	0.0529 (10)	0.0828 (11)	−0.0024 (8)	0.0185 (9)	0.0020 (8)
N3	0.0537 (9)	0.0551 (10)	0.0745 (10)	0.0032 (7)	0.0082 (8)	−0.0037 (8)
N4	0.0340 (7)	0.0564 (9)	0.0449 (7)	0.0033 (6)	−0.0006 (6)	−0.0009 (7)
N5	0.0567 (9)	0.0622 (10)	0.0506 (8)	0.0045 (8)	−0.0146 (7)	0.0007 (8)
N6	0.0415 (8)	0.0599 (9)	0.0540 (8)	0.0055 (7)	−0.0122 (6)	−0.0064 (8)
N7	0.0380 (7)	0.0464 (8)	0.0404 (7)	0.0006 (6)	−0.0078 (6)	−0.0032 (6)
C1	0.0413 (9)	0.0360 (9)	0.0420 (8)	−0.0034 (7)	0.0003 (7)	0.0067 (7)
C2	0.0333 (8)	0.0653 (12)	0.0522 (10)	−0.0014 (8)	0.0041 (7)	0.0077 (9)
C3	0.0469 (10)	0.0700 (12)	0.0468 (10)	0.0091 (9)	0.0130 (8)	0.0002 (9)
C4	0.0463 (9)	0.0569 (10)	0.0360 (8)	0.0023 (8)	0.0048 (7)	−0.0010 (8)
C5	0.0396 (8)	0.0427 (9)	0.0346 (8)	0.0028 (7)	0.0015 (6)	0.0043 (7)
C6	0.0407 (9)	0.0745 (12)	0.0374 (8)	0.0076 (8)	−0.0007 (7)	−0.0029 (8)
C7	0.0397 (9)	0.0504 (10)	0.0485 (9)	−0.0027 (8)	0.0016 (7)	0.0027 (8)
C8	0.0318 (8)	0.0521 (10)	0.0353 (8)	0.0015 (7)	−0.0046 (6)	0.0002 (7)
C9	0.0514 (10)	0.0551 (11)	0.0444 (9)	−0.0077 (8)	0.0019 (8)	0.0034 (8)
C10	0.0687 (12)	0.0514 (11)	0.0535 (11)	0.0007 (9)	0.0032 (9)	−0.0045 (9)
C11	0.0584 (11)	0.0699 (13)	0.0502 (10)	0.0076 (10)	0.0126 (8)	−0.0051 (9)
C12	0.0500 (10)	0.0668 (13)	0.0564 (11)	−0.0043 (9)	0.0137 (8)	0.0033 (9)
C13	0.0524 (10)	0.0440 (10)	0.0510 (10)	−0.0108 (8)	−0.0040 (8)	−0.0008 (8)
C14	0.0552 (10)	0.0433 (9)	0.0406 (9)	−0.0013 (8)	−0.0076 (7)	−0.0074 (7)
C15	0.0411 (8)	0.0400 (9)	0.0431 (8)	−0.0012 (7)	−0.0045 (7)	−0.0055 (7)
C16	0.0422 (9)	0.0641 (12)	0.0675 (11)	−0.0003 (9)	−0.0066 (8)	0.0026 (10)
C17	0.0473 (11)	0.0816 (15)	0.0910 (15)	−0.0068 (10)	0.0085 (11)	−0.0046 (13)
C18	0.0772 (15)	0.0758 (15)	0.0695 (13)	−0.0213 (12)	0.0208 (11)	−0.0101 (12)
C19	0.0866 (15)	0.0559 (12)	0.0473 (10)	−0.0134 (10)	−0.0011 (10)	−0.0029 (9)

Geometric parameters (Å, º)

N1—C1	1.3332 (19)	C7—C8	1.386 (2)
N1—C5	1.3377 (19)	C7—C12	1.397 (2)
N2—N3	1.307 (2)	C8—C9	1.389 (2)
N2—C7	1.373 (2)	C9—C10	1.368 (2)
N3—N4	1.354 (2)	C9—H9	0.93
N4—C8	1.358 (2)	C10—C11	1.406 (3)
N4—C6	1.4496 (19)	C10—H10	0.93
N5—N6	1.299 (2)	C11—C12	1.357 (3)
N5—C14	1.371 (2)	C11—H11	0.93
N6—N7	1.3538 (18)	C12—H12	0.93
N7—C15	1.3603 (19)	C13—H13A	0.97
N7—C13	1.457 (2)	C13—H13B	0.97
C1—C2	1.378 (2)	C14—C15	1.389 (2)
C1—C13	1.506 (2)	C14—C19	1.396 (2)
C2—C3	1.377 (2)	C15—C16	1.391 (2)
C2—H2	0.93	C16—C17	1.365 (3)
C3—C4	1.373 (2)	C16—H16	0.93
C3—H3	0.93	C17—C18	1.404 (3)
C4—C5	1.382 (2)	C17—H17	0.93
C4—H4	0.93	C18—C19	1.357 (3)
C5—C6	1.497 (2)	C18—H18	0.93
C6—H6A	0.97	C19—H19	0.93
C6—H6B	0.97
C1—N1—C5	117.80 (13)	C7—C8—C9	122.59 (15)
N3—N2—C7	107.83 (14)	C10—C9—C8	116.17 (16)
N2—N3—N4	108.90 (14)	C10—C9—H9	121.9
N3—N4—C8	110.1 (1)	C8—C9—H9	121.9
N3—N4—C6	120.1 (1)	C9—C10—C11	121.85 (18)
C8—N4—C6	129.2 (2)	C9—C10—H10	119.1
N6—N5—C14	108.13 (13)	C11—C10—H10	119.1
N5—N6—N7	109.07 (13)	C12—C11—C10	121.56 (17)
N6—N7—C15	110.0 (1)	C12—C11—H11	119.2
N6—N7—C13	118.8 (1)	C10—C11—H11	119.2
C15—N7—C13	130.6 (1)	C11—C12—C7	117.56 (17)
N1—C1—C2	123.08 (14)	C11—C12—H12	121.2
N1—C1—C13	115.19 (14)	C7—C12—H12	121.2
C2—C1—C13	121.73 (14)	N7—C13—C1	113.57 (12)
C3—C2—C1	118.62 (15)	N7—C13—H13A	108.9
C3—C2—H2	120.7	C1—C13—H13A	108.9
C1—C2—H2	120.7	N7—C13—H13B	108.9
C4—C3—C2	119.00 (15)	C1—C13—H13B	108.9
C4—C3—H3	120.5	H13A—C13—H13B	107.7
C2—C3—H3	120.5	N5—C14—C15	108.75 (15)
C3—C4—C5	118.96 (15)	N5—C14—C19	130.34 (16)
C3—C4—H4	120.5	C15—C14—C19	120.88 (16)
C5—C4—H4	120.5	N7—C15—C14	104.07 (13)
N1—C5—C4	122.53 (14)	N7—C15—C16	133.91 (15)
N1—C5—C6	116.76 (13)	C14—C15—C16	122.02 (16)
C4—C5—C6	120.64 (14)	C17—C16—C15	116.13 (17)
N4—C6—C5	114.35 (13)	C17—C16—H16	121.9
N4—C6—H6A	108.7	C15—C16—H16	121.9
C5—C6—H6A	108.7	C16—C17—C18	122.28 (19)
N4—C6—H6B	108.7	C16—C17—H17	118.9
C5—C6—H6B	108.7	C18—C17—H17	118.9
H6A—C6—H6B	107.6	C19—C18—C17	121.54 (19)
N2—C7—C8	108.89 (14)	C19—C18—H18	119.2
N2—C7—C12	130.80 (16)	C17—C18—H18	119.2
C8—C7—C12	120.25 (16)	C18—C19—C14	117.13 (18)
N4—C8—C7	104.26 (14)	C18—C19—H19	121.4
N4—C8—C9	133.14 (15)	C14—C19—H19	121.4
C7—N2—N3—N4	−1.10 (19)	C12—C7—C8—C9	−1.6 (2)
N2—N3—N4—C8	1.00 (18)	N4—C8—C9—C10	−177.56 (15)
N2—N3—N4—C6	172.69 (14)	C7—C8—C9—C10	1.3 (2)
C14—N5—N6—N7	1.04 (18)	C8—C9—C10—C11	−0.1 (2)
N5—N6—N7—C15	−0.53 (18)	C9—C10—C11—C12	−0.8 (3)
N5—N6—N7—C13	−172.11 (13)	C10—C11—C12—C7	0.4 (3)
C5—N1—C1—C2	−0.8 (2)	N2—C7—C12—C11	177.83 (18)
C5—N1—C1—C13	179.01 (13)	C8—C7—C12—C11	0.7 (2)
N1—C1—C2—C3	0.8 (2)	N6—N7—C13—C1	−111.93 (15)
C13—C1—C2—C3	−178.96 (15)	C15—N7—C13—C1	78.5 (2)
C1—C2—C3—C4	−0.4 (3)	N1—C1—C13—N7	−82.23 (17)
C2—C3—C4—C5	−0.1 (3)	C2—C1—C13—N7	97.54 (18)
C1—N1—C5—C4	0.3 (2)	N6—N5—C14—C15	−1.17 (19)
C1—N1—C5—C6	177.19 (14)	N6—N5—C14—C19	176.73 (17)
C3—C4—C5—N1	0.1 (2)	N6—N7—C15—C14	−0.20 (17)
C3—C4—C5—C6	−176.68 (16)	C13—N7—C15—C14	170.09 (14)
N3—N4—C6—C5	91.04 (18)	N6—N7—C15—C16	−179.11 (18)
C8—N4—C6—C5	−99.05 (17)	C13—N7—C15—C16	−8.8 (3)
N1—C5—C6—N4	43.1 (2)	N5—C14—C15—N7	0.82 (17)
C4—C5—C6—N4	−139.94 (16)	C19—C14—C15—N7	−177.31 (15)
N3—N2—C7—C8	0.81 (19)	N5—C14—C15—C16	179.89 (15)
N3—N2—C7—C12	−176.56 (17)	C19—C14—C15—C16	1.8 (2)
N3—N4—C8—C7	−0.47 (16)	N7—C15—C16—C17	177.54 (18)
C6—N4—C8—C7	−171.18 (14)	C14—C15—C16—C17	−1.2 (3)
N3—N4—C8—C9	178.50 (16)	C15—C16—C17—C18	0.0 (3)
C6—N4—C8—C9	7.8 (3)	C16—C17—C18—C19	0.7 (3)
N2—C7—C8—N4	−0.20 (17)	C17—C18—C19—C14	−0.1 (3)
C12—C7—C8—N4	177.50 (14)	N5—C14—C19—C18	−178.7 (2)
N2—C7—C8—C9	−179.31 (15)	C15—C14—C19—C18	−1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1	0.93	2.78	3.385 (2)	124
C6—H6A···N3^i	0.97	2.78	3.734 (2)	170
C13—H13B···N3^ii	0.97	2.82	3.718 (2)	154
C9—H9···N6^ii	0.93	2.49	3.405 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2.