2-(1H-Benzotriazol-1-yl)-1-(3-methoxy-benzo-yl)ethyl isonicotinate.

In the title compound, C(22)H(18)N(4)O(4), mol-ecules are linked to each other by C-H⋯N and C-H⋯O inter-molecular hydrogen-bonding inter-actions. The crystal packing is further stabilized by C-H⋯π, and π-π inter-actions with a distance of 3.783 (3) Å between the centroids of the benzene rings of the benzotriazole system.

Related literature

For general background on benzotriazole and its derivatives, see: Chen & Wu (2005 ▶). For details of the synthesis, see: Wan et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H18N4O4

M = 402.40

Triclinic,

a = 9.4839 (18) Å

b = 10.3611 (19) Å

c = 11.276 (2) Å

α = 109.342 (3)°

β = 102.664 (3)°

γ = 97.985 (3)°

V = 992.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.33 × 0.16 × 0.08 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.992

5605 measured reflections

3819 independent reflections

2822 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.04

3819 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001196/at2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001196/at2705Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H18N4O4	Z = 2
Mr = 402.40	F(000) = 420
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4839 (18) Å	Cell parameters from 1711 reflections
b = 10.3611 (19) Å	θ = 2.6–24.7°
c = 11.276 (2) Å	µ = 0.10 mm−1
α = 109.342 (3)°	T = 293 K
β = 102.664 (3)°	Plate, colourless
γ = 97.985 (3)°	0.33 × 0.16 × 0.08 mm
V = 992.8 (3) Å3

Siemens SMART 1000 CCD area-detector diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	2822 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 8.33 pixels mm-1	θmax = 26.1°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→10
Tmin = 0.969, Tmax = 0.992	l = −12→13
5605 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.1574P] where P = (Fo2 + 2Fc2)/3
3819 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
O2	0.21549 (13)	0.94145 (12)	0.45684 (11)	0.0511 (3)
O3	0.40290 (15)	1.11047 (14)	0.47141 (13)	0.0639 (4)
N1	0.22089 (16)	0.73861 (15)	0.58935 (14)	0.0498 (4)
C7	0.23974 (18)	1.12532 (18)	0.66726 (18)	0.0474 (4)
C6	0.31816 (18)	1.19911 (18)	0.80934 (17)	0.0457 (4)
C17	0.23003 (19)	0.97219 (18)	0.26265 (17)	0.0481 (4)
C1	0.2728 (2)	1.31472 (19)	0.88006 (18)	0.0526 (5)
H1A	0.1952	1.3441	0.8379	0.063*
C16	0.29418 (19)	1.01773 (19)	0.40669 (18)	0.0487 (4)
O1	0.15281 (15)	1.17332 (14)	0.60783 (13)	0.0691 (4)
C8	0.26559 (19)	0.98062 (18)	0.59616 (17)	0.0474 (4)
H8A	0.3712	0.9811	0.6233	0.057*
N2	0.34386 (18)	0.72584 (18)	0.66902 (16)	0.0642 (5)
C10	0.16172 (19)	0.61663 (18)	0.48299 (17)	0.0457 (4)
C21	0.2851 (2)	1.0500 (2)	0.19695 (19)	0.0556 (5)
H21A	0.3604	1.1310	0.2422	0.067*
C9	0.1742 (2)	0.86971 (18)	0.62674 (18)	0.0498 (4)
H9A	0.1837	0.9040	0.7199	0.060*
H9B	0.0704	0.8535	0.5805	0.060*
C15	0.0363 (2)	0.57215 (19)	0.37579 (18)	0.0524 (5)
H15A	−0.0264	0.6310	0.3634	0.063*
N3	0.36612 (19)	0.60040 (18)	0.61744 (17)	0.0687 (5)
O4	0.28449 (18)	1.49647 (15)	1.07256 (15)	0.0812 (5)
C11	0.2550 (2)	0.52895 (19)	0.50226 (18)	0.0522 (5)
C5	0.4361 (2)	1.1570 (2)	0.87303 (19)	0.0565 (5)
H5A	0.4675	1.0791	0.8273	0.068*
C2	0.3411 (2)	1.38696 (19)	1.01200 (19)	0.0551 (5)
N4	0.1207 (2)	0.8890 (2)	−0.00867 (17)	0.0771 (5)
C3	0.4587 (2)	1.3456 (2)	1.0743 (2)	0.0626 (5)
H3B	0.5059	1.3944	1.1632	0.075*
C12	0.2266 (2)	0.3910 (2)	0.4131 (2)	0.0615 (5)
H12A	0.2887	0.3316	0.4253	0.074*
C14	0.0107 (2)	0.4364 (2)	0.28959 (19)	0.0604 (5)
H14A	−0.0717	0.4024	0.2164	0.072*
C4	0.5054 (2)	1.2319 (2)	1.0041 (2)	0.0670 (6)
H4B	0.5854	1.2052	1.0460	0.080*
C13	0.1044 (2)	0.3469 (2)	0.3078 (2)	0.0627 (5)
H13A	0.0826	0.2555	0.2466	0.075*
C20	0.2260 (2)	1.0049 (2)	0.0634 (2)	0.0680 (6)
H20A	0.2622	1.0593	0.0207	0.082*
C19	0.0693 (3)	0.8157 (3)	0.0559 (2)	0.0825 (7)
H19A	−0.0042	0.7339	0.0076	0.099*
C22	0.3532 (3)	1.5758 (2)	1.2089 (2)	0.0840 (7)
H22A	0.3031	1.6493	1.2391	0.126*
H22B	0.4555	1.6163	1.2223	0.126*
H22C	0.3471	1.5151	1.2570	0.126*
C18	0.1180 (2)	0.8531 (2)	0.1897 (2)	0.0695 (6)
H18A	0.0762	0.7991	0.2302	0.083*

	U11	U22	U33	U12	U13	U23
O2	0.0529 (7)	0.0520 (7)	0.0458 (7)	0.0072 (6)	0.0145 (6)	0.0166 (6)
O3	0.0558 (8)	0.0645 (9)	0.0632 (9)	−0.0020 (7)	0.0069 (7)	0.0265 (7)
N1	0.0547 (9)	0.0462 (9)	0.0449 (9)	0.0113 (7)	0.0066 (7)	0.0176 (7)
C7	0.0417 (9)	0.0488 (10)	0.0528 (11)	0.0117 (8)	0.0111 (8)	0.0213 (8)
C6	0.0435 (9)	0.0445 (10)	0.0490 (11)	0.0063 (8)	0.0119 (8)	0.0196 (8)
C17	0.0463 (10)	0.0511 (11)	0.0494 (11)	0.0166 (8)	0.0176 (8)	0.0172 (8)
C1	0.0477 (10)	0.0533 (11)	0.0565 (12)	0.0135 (8)	0.0109 (9)	0.0219 (9)
C16	0.0473 (10)	0.0476 (10)	0.0546 (11)	0.0149 (9)	0.0175 (9)	0.0199 (9)
O1	0.0717 (9)	0.0700 (9)	0.0587 (9)	0.0335 (8)	0.0025 (7)	0.0186 (7)
C8	0.0464 (10)	0.0486 (10)	0.0451 (10)	0.0114 (8)	0.0100 (8)	0.0165 (8)
N2	0.0651 (10)	0.0611 (11)	0.0550 (10)	0.0141 (8)	−0.0021 (8)	0.0197 (8)
C10	0.0511 (10)	0.0447 (10)	0.0426 (10)	0.0100 (8)	0.0128 (8)	0.0187 (8)
C21	0.0563 (11)	0.0538 (11)	0.0557 (12)	0.0126 (9)	0.0174 (9)	0.0185 (9)
C9	0.0546 (10)	0.0456 (10)	0.0479 (10)	0.0106 (8)	0.0146 (8)	0.0162 (8)
C15	0.0529 (11)	0.0565 (11)	0.0493 (11)	0.0154 (9)	0.0121 (9)	0.0221 (9)
N3	0.0723 (11)	0.0633 (11)	0.0633 (11)	0.0238 (9)	0.0017 (9)	0.0226 (9)
O4	0.0977 (11)	0.0704 (10)	0.0664 (10)	0.0311 (9)	0.0243 (9)	0.0088 (8)
C11	0.0577 (11)	0.0528 (11)	0.0476 (11)	0.0157 (9)	0.0101 (9)	0.0226 (9)
C5	0.0577 (11)	0.0552 (11)	0.0558 (12)	0.0196 (9)	0.0119 (9)	0.0196 (9)
C2	0.0593 (11)	0.0491 (11)	0.0535 (12)	0.0076 (9)	0.0178 (9)	0.0154 (9)
N4	0.0788 (12)	0.0912 (14)	0.0529 (11)	0.0082 (11)	0.0183 (10)	0.0213 (10)
C3	0.0667 (13)	0.0630 (13)	0.0483 (12)	0.0062 (10)	0.0070 (10)	0.0178 (10)
C12	0.0742 (13)	0.0531 (12)	0.0641 (13)	0.0248 (10)	0.0225 (11)	0.0245 (10)
C14	0.0603 (12)	0.0626 (13)	0.0485 (11)	0.0075 (10)	0.0118 (9)	0.0135 (9)
C4	0.0646 (13)	0.0745 (14)	0.0564 (13)	0.0205 (11)	0.0018 (10)	0.0258 (11)
C13	0.0761 (14)	0.0468 (11)	0.0595 (13)	0.0099 (10)	0.0231 (11)	0.0120 (9)
C20	0.0751 (14)	0.0726 (15)	0.0586 (13)	0.0117 (12)	0.0235 (11)	0.0266 (11)
C19	0.0799 (16)	0.0866 (17)	0.0563 (14)	−0.0113 (13)	0.0136 (12)	0.0116 (12)
C22	0.1063 (19)	0.0643 (14)	0.0660 (15)	0.0046 (13)	0.0360 (14)	0.0037 (11)
C18	0.0672 (13)	0.0733 (14)	0.0575 (13)	−0.0036 (11)	0.0170 (11)	0.0194 (11)

O2—C16	1.349 (2)	C15—H15A	0.9300
O2—C8	1.434 (2)	N3—C11	1.375 (2)
O3—C16	1.204 (2)	O4—C2	1.363 (2)
N1—N2	1.359 (2)	O4—C22	1.428 (2)
N1—C10	1.362 (2)	C11—C12	1.396 (3)
N1—C9	1.445 (2)	C5—C4	1.375 (3)
C7—O1	1.212 (2)	C5—H5A	0.9300
C7—C6	1.488 (2)	C2—C3	1.382 (3)
C7—C8	1.531 (2)	N4—C19	1.327 (3)
C6—C1	1.384 (2)	N4—C20	1.329 (3)
C6—C5	1.395 (2)	C3—C4	1.376 (3)
C17—C18	1.382 (3)	C3—H3B	0.9300
C17—C21	1.385 (3)	C12—C13	1.361 (3)
C17—C16	1.487 (2)	C12—H12A	0.9300
C1—C2	1.378 (3)	C14—C13	1.403 (3)
C1—H1A	0.9300	C14—H14A	0.9300
C8—C9	1.519 (2)	C4—H4B	0.9300
C8—H8A	0.9800	C13—H13A	0.9300
N2—N3	1.304 (2)	C20—H20A	0.9300
C10—C11	1.387 (2)	C19—C18	1.378 (3)
C10—C15	1.392 (2)	C19—H19A	0.9300
C21—C20	1.375 (3)	C22—H22A	0.9600
C21—H21A	0.9300	C22—H22B	0.9600
C9—H9A	0.9700	C22—H22C	0.9600
C9—H9B	0.9700	C18—H18A	0.9300
C15—C14	1.371 (3)
C16—O2—C8	115.78 (13)	C2—O4—C22	117.93 (18)
N2—N1—C10	109.89 (14)	N3—C11—C10	108.94 (16)
N2—N1—C9	118.99 (14)	N3—C11—C12	130.21 (18)
C10—N1—C9	131.12 (15)	C10—C11—C12	120.83 (17)
O1—C7—C6	122.39 (16)	C4—C5—C6	119.33 (18)
O1—C7—C8	119.34 (16)	C4—C5—H5A	120.3
C6—C7—C8	118.21 (15)	C6—C5—H5A	120.3
C1—C6—C5	119.12 (17)	O4—C2—C1	115.94 (18)
C1—C6—C7	118.39 (15)	O4—C2—C3	124.37 (18)
C5—C6—C7	122.49 (16)	C1—C2—C3	119.69 (18)
C18—C17—C21	117.82 (18)	C19—N4—C20	116.16 (19)
C18—C17—C16	122.72 (18)	C4—C3—C2	119.54 (19)
C21—C17—C16	119.45 (17)	C4—C3—H3B	120.2
C2—C1—C6	120.96 (17)	C2—C3—H3B	120.2
C2—C1—H1A	119.5	C13—C12—C11	117.29 (18)
C6—C1—H1A	119.5	C13—C12—H12A	121.4
O3—C16—O2	123.70 (17)	C11—C12—H12A	121.4
O3—C16—C17	124.81 (18)	C15—C14—C13	122.40 (19)
O2—C16—C17	111.49 (15)	C15—C14—H14A	118.8
O2—C8—C9	106.06 (13)	C13—C14—H14A	118.8
O2—C8—C7	110.80 (14)	C5—C4—C3	121.34 (19)
C9—C8—C7	109.81 (14)	C5—C4—H4B	119.3
O2—C8—H8A	110.0	C3—C4—H4B	119.3
C9—C8—H8A	110.0	C12—C13—C14	121.34 (18)
C7—C8—H8A	110.0	C12—C13—H13A	119.3
N3—N2—N1	109.04 (15)	C14—C13—H13A	119.3
N1—C10—C11	104.25 (15)	N4—C20—C21	124.4 (2)
N1—C10—C15	133.49 (16)	N4—C20—H20A	117.8
C11—C10—C15	122.22 (16)	C21—C20—H20A	117.8
C20—C21—C17	118.61 (19)	N4—C19—C18	124.2 (2)
C20—C21—H21A	120.7	N4—C19—H19A	117.9
C17—C21—H21A	120.7	C18—C19—H19A	117.9
N1—C9—C8	111.93 (14)	O4—C22—H22A	109.5
N1—C9—H9A	109.2	O4—C22—H22B	109.5
C8—C9—H9A	109.2	H22A—C22—H22B	109.5
N1—C9—H9B	109.2	O4—C22—H22C	109.5
C8—C9—H9B	109.2	H22A—C22—H22C	109.5
H9A—C9—H9B	107.9	H22B—C22—H22C	109.5
C14—C15—C10	115.92 (17)	C19—C18—C17	118.8 (2)
C14—C15—H15A	122.0	C19—C18—H18A	120.6
C10—C15—H15A	122.0	C17—C18—H18A	120.6
N2—N3—C11	107.87 (15)
O1—C7—C6—C1	10.4 (3)	N1—C10—C15—C14	−177.61 (19)
C8—C7—C6—C1	−166.80 (16)	C11—C10—C15—C14	−0.4 (3)
O1—C7—C6—C5	−168.84 (18)	N1—N2—N3—C11	−0.5 (2)
C8—C7—C6—C5	13.9 (3)	N2—N3—C11—C10	0.6 (2)
C5—C6—C1—C2	−0.9 (3)	N2—N3—C11—C12	−177.9 (2)
C7—C6—C1—C2	179.82 (17)	N1—C10—C11—N3	−0.4 (2)
C8—O2—C16—O3	2.3 (2)	C15—C10—C11—N3	−178.31 (17)
C8—O2—C16—C17	−177.93 (13)	N1—C10—C11—C12	178.28 (18)
C18—C17—C16—O3	170.73 (19)	C15—C10—C11—C12	0.4 (3)
C21—C17—C16—O3	−8.3 (3)	C1—C6—C5—C4	−0.6 (3)
C18—C17—C16—O2	−9.0 (2)	C7—C6—C5—C4	178.69 (18)
C21—C17—C16—O2	172.00 (15)	C22—O4—C2—C1	−179.05 (18)
C16—O2—C8—C9	−172.79 (13)	C22—O4—C2—C3	1.4 (3)
C16—O2—C8—C7	68.10 (18)	C6—C1—C2—O4	−178.11 (17)
O1—C7—C8—O2	18.0 (2)	C6—C1—C2—C3	1.5 (3)
C6—C7—C8—O2	−164.64 (14)	O4—C2—C3—C4	178.9 (2)
O1—C7—C8—C9	−98.8 (2)	C1—C2—C3—C4	−0.6 (3)
C6—C7—C8—C9	78.53 (19)	N3—C11—C12—C13	178.3 (2)
C10—N1—N2—N3	0.3 (2)	C10—C11—C12—C13	−0.1 (3)
C9—N1—N2—N3	−179.98 (16)	C10—C15—C14—C13	0.2 (3)
N2—N1—C10—C11	0.1 (2)	C6—C5—C4—C3	1.5 (3)
C9—N1—C10—C11	−179.61 (17)	C2—C3—C4—C5	−0.9 (3)
N2—N1—C10—C15	177.64 (19)	C11—C12—C13—C14	−0.1 (3)
C9—N1—C10—C15	−2.1 (3)	C15—C14—C13—C12	0.0 (3)
C18—C17—C21—C20	−0.1 (3)	C19—N4—C20—C21	1.4 (3)
C16—C17—C21—C20	178.95 (17)	C17—C21—C20—N4	−1.5 (3)
N2—N1—C9—C8	79.2 (2)	C20—N4—C19—C18	0.2 (4)
C10—N1—C9—C8	−101.1 (2)	N4—C19—C18—C17	−1.7 (4)
O2—C8—C9—N1	74.36 (17)	C21—C17—C18—C19	1.6 (3)
C7—C8—C9—N1	−165.87 (14)	C16—C17—C18—C19	−177.42 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···N3i	0.93	2.48	3.328 (3)	151
C9—H9B···O1ii	0.97	2.56	3.471 (2)	157
C15—H15A···O1ii	0.93	2.46	3.368 (3)	164
C20—H20A···Cg3iii	0.93	2.85	3.767	168
C22—H22C···Cg4iv	0.96	2.87	3.530	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯N3i	0.93	2.48	3.328 (3)	151
C9—H9B⋯O1ii	0.97	2.56	3.471 (2)	157
C15—H15A⋯O1ii	0.93	2.46	3.368 (3)	164
C20—H20A⋯Cg3iii	0.93	2.85	3.767	168
C22—H22C⋯Cg4iv	0.96	2.87	3.530	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .