3-(Benzotriazol-1-yl)-1-(p-tol­yl)-2-(1H-1,2,4-triazol-2-yl)propan-1-one

In the title mol­ecule, C₁₈H₁₆N₆O, the central triazole ring is approximately perpendicular to the tolyl group [dihedral angle 85.4 (1)°] and makes a dihedral angle of 46.4 (1)° with the benzotriazole group. C—H...N, C—H...O and π–π inter­actions link the mol­ecules into a two-dimensional network parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.115
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(Benzotriazol-1-yl)-1-(p-tolyl)-2-(1H-1,2,4-triazol-2-yl)propan-1-one

Crystal data

C18H16N6O	F(000) = 1392
Mr = 332.37	Dx = 1.336 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2365 reflections
a = 30.972 (3) Å	θ = 2.8–23.4°
b = 8.1625 (8) Å	µ = 0.09 mm^−1
c = 14.6599 (14) Å	T = 293 K
β = 116.927 (1)°	Block, colourless
V = 3304.4 (6) Å^3	0.21 × 0.17 × 0.12 mm
Z = 8

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3249 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −29→38
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→9
Tmin = 0.982, Tmax = 0.989	l = −18→16
8988 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 1.0955P] where P = (Fo^2 + 2Fc^2)/3
3249 reflections	(Δ/σ)max = 0.031
227 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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
O1	0.08098 (5)	0.43974 (16)	0.18793 (9)	0.0665 (4)
N1	0.20479 (5)	0.53170 (16)	0.45005 (10)	0.0447 (3)
N2	0.24836 (5)	0.46131 (18)	0.47956 (11)	0.0533 (4)
N3	0.27683 (5)	0.50472 (18)	0.57360 (12)	0.0576 (4)
N4	0.13110 (4)	0.30689 (15)	0.42742 (9)	0.0403 (3)
N5	0.09538 (5)	0.39525 (18)	0.43336 (11)	0.0527 (4)
N6	0.13335 (6)	0.2376 (3)	0.57259 (12)	0.0774 (5)
C1	0.08980 (6)	0.0115 (2)	0.24572 (14)	0.0535 (4)
H1	0.1225	0.0047	0.2916	0.064*
C2	0.06282 (7)	−0.1298 (2)	0.20992 (15)	0.0599 (5)
H2	0.0780	−0.2309	0.2308	0.072*
C3	0.01397 (6)	−0.1248 (2)	0.14395 (14)	0.0549 (5)
C4	−0.00743 (6)	0.0271 (2)	0.11411 (14)	0.0610 (5)
H4	−0.0405	0.0337	0.0706	0.073*
C5	0.01909 (6)	0.1686 (2)	0.14745 (13)	0.0550 (5)
H5	0.0039	0.2695	0.1256	0.066*
C6	0.06828 (6)	0.16283 (19)	0.21348 (11)	0.0429 (4)
C7	0.09531 (6)	0.3193 (2)	0.24172 (12)	0.0443 (4)
C8	0.14239 (6)	0.33204 (19)	0.34255 (11)	0.0412 (4)
H8	0.1649	0.2464	0.3439	0.049*
C9	0.16575 (6)	0.4997 (2)	0.34939 (13)	0.0513 (4)
H9A	0.1782	0.5050	0.2995	0.062*
H9B	0.1413	0.5842	0.3325	0.062*
C10	0.20468 (6)	0.62330 (19)	0.52762 (12)	0.0445 (4)
C11	0.25117 (6)	0.6056 (2)	0.60607 (13)	0.0496 (4)
C12	0.26521 (9)	0.6824 (2)	0.70028 (15)	0.0706 (6)
H12	0.2964	0.6713	0.7534	0.085*
C13	0.23123 (12)	0.7740 (3)	0.71050 (19)	0.0868 (8)
H13	0.2393	0.8260	0.7726	0.104*
C14	0.18415 (10)	0.7933 (3)	0.6306 (2)	0.0835 (7)
H14	0.1622	0.8585	0.6411	0.100*
C15	0.16981 (7)	0.7188 (2)	0.53777 (17)	0.0661 (5)
H15	0.1387	0.7311	0.4847	0.079*
C16	0.15291 (7)	0.2165 (3)	0.51059 (14)	0.0648 (5)
H16	0.1788	0.1468	0.5236	0.078*
C17	0.09854 (7)	0.3476 (3)	0.52129 (14)	0.0601 (5)
H17	0.0780	0.3874	0.5467	0.072*
C18	−0.01541 (8)	−0.2794 (3)	0.10510 (18)	0.0784 (6)
H18A	−0.0375	−0.2671	0.0338	0.118*
H18B	−0.0334	−0.2996	0.1429	0.118*
H18C	0.0059	−0.3700	0.1139	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0686 (9)	0.0567 (8)	0.0511 (7)	−0.0057 (7)	0.0068 (6)	0.0152 (6)
N1	0.0387 (8)	0.0449 (8)	0.0466 (8)	−0.0026 (6)	0.0159 (6)	−0.0021 (6)
N2	0.0439 (8)	0.0525 (9)	0.0612 (10)	0.0014 (7)	0.0219 (7)	−0.0024 (7)
N3	0.0466 (9)	0.0534 (9)	0.0599 (9)	−0.0001 (7)	0.0129 (7)	−0.0003 (7)
N4	0.0361 (7)	0.0437 (7)	0.0375 (7)	0.0028 (6)	0.0134 (6)	0.0005 (6)
N5	0.0463 (8)	0.0579 (9)	0.0565 (9)	0.0084 (7)	0.0254 (7)	−0.0020 (7)
N6	0.0628 (11)	0.1235 (15)	0.0520 (9)	0.0225 (11)	0.0313 (8)	0.0218 (10)
C1	0.0394 (9)	0.0517 (10)	0.0576 (10)	0.0023 (8)	0.0116 (8)	−0.0029 (8)
C2	0.0514 (11)	0.0452 (10)	0.0732 (12)	0.0030 (8)	0.0197 (9)	−0.0031 (9)
C3	0.0498 (11)	0.0556 (11)	0.0572 (11)	−0.0075 (9)	0.0224 (9)	−0.0086 (9)
C4	0.0385 (10)	0.0680 (13)	0.0602 (11)	−0.0034 (9)	0.0080 (8)	−0.0020 (9)
C5	0.0454 (10)	0.0519 (10)	0.0539 (10)	0.0046 (8)	0.0103 (8)	0.0039 (8)
C6	0.0412 (9)	0.0481 (9)	0.0366 (8)	−0.0004 (7)	0.0151 (7)	−0.0012 (7)
C7	0.0464 (9)	0.0465 (9)	0.0376 (8)	0.0003 (7)	0.0170 (7)	0.0021 (7)
C8	0.0401 (9)	0.0430 (9)	0.0397 (8)	0.0001 (7)	0.0173 (7)	−0.0004 (7)
C9	0.0505 (10)	0.0507 (10)	0.0445 (9)	−0.0058 (8)	0.0141 (8)	0.0034 (8)
C10	0.0485 (10)	0.0365 (8)	0.0518 (10)	−0.0055 (7)	0.0254 (8)	−0.0020 (7)
C11	0.0558 (11)	0.0390 (9)	0.0494 (10)	−0.0095 (8)	0.0198 (8)	−0.0009 (8)
C12	0.0943 (16)	0.0514 (11)	0.0535 (12)	−0.0183 (11)	0.0224 (11)	−0.0059 (9)
C13	0.144 (3)	0.0584 (13)	0.0701 (15)	−0.0201 (15)	0.0589 (17)	−0.0173 (11)
C14	0.115 (2)	0.0558 (12)	0.114 (2)	−0.0026 (13)	0.0819 (19)	−0.0156 (13)
C15	0.0626 (12)	0.0537 (11)	0.0907 (15)	−0.0006 (9)	0.0424 (11)	−0.0075 (10)
C16	0.0563 (11)	0.0880 (14)	0.0531 (11)	0.0264 (10)	0.0274 (9)	0.0240 (10)
C17	0.0489 (11)	0.0838 (14)	0.0518 (11)	−0.0019 (10)	0.0265 (9)	−0.0126 (10)
C18	0.0652 (13)	0.0673 (13)	0.0917 (16)	−0.0181 (11)	0.0259 (12)	−0.0178 (12)

Geometric parameters (Å, º)

O1—C7	1.2115 (19)	C5—H5	0.93
N1—N2	1.3453 (18)	C6—C7	1.480 (2)
N1—C10	1.362 (2)	C7—C8	1.539 (2)
N1—C9	1.446 (2)	C8—C9	1.530 (2)
N2—N3	1.305 (2)	C8—H8	0.98
N3—C11	1.371 (2)	C9—H9A	0.97
N4—C16	1.320 (2)	C9—H9B	0.97
N4—N5	1.3561 (18)	C10—C11	1.384 (2)
N4—C8	1.4513 (19)	C10—C15	1.393 (2)
N5—C17	1.307 (2)	C11—C12	1.395 (3)
N6—C16	1.312 (2)	C12—C13	1.353 (3)
N6—C17	1.341 (2)	C12—H12	0.93
C1—C2	1.381 (2)	C13—C14	1.406 (4)
C1—C6	1.382 (2)	C13—H13	0.93
C1—H1	0.93	C14—C15	1.368 (3)
C2—C3	1.379 (3)	C14—H14	0.93
C2—H2	0.93	C15—H15	0.93
C3—C4	1.380 (3)	C16—H16	0.93
C3—C18	1.509 (3)	C17—H17	0.93
C4—C5	1.373 (2)	C18—H18A	0.96
C4—H4	0.93	C18—H18B	0.96
C5—C6	1.388 (2)	C18—H18C	0.96
N2—N1—C10	110.32 (13)	N1—C9—C8	112.36 (13)
N2—N1—C9	120.29 (14)	N1—C9—H9A	109.1
C10—N1—C9	129.34 (14)	C8—C9—H9A	109.1
N3—N2—N1	108.86 (14)	N1—C9—H9B	109.1
N2—N3—C11	108.03 (14)	C8—C9—H9B	109.1
C16—N4—N5	109.22 (14)	H9A—C9—H9B	107.9
C16—N4—C8	130.54 (14)	N1—C10—C11	103.98 (14)
N5—N4—C8	120.00 (12)	N1—C10—C15	133.72 (17)
C17—N5—N4	101.89 (14)	C11—C10—C15	122.30 (17)
C16—N6—C17	101.86 (15)	N3—C11—C10	108.81 (15)
C2—C1—C6	120.13 (16)	N3—C11—C12	130.09 (18)
C2—C1—H1	119.9	C10—C11—C12	121.10 (18)
C6—C1—H1	119.9	C13—C12—C11	116.6 (2)
C3—C2—C1	121.64 (17)	C13—C12—H12	121.7
C3—C2—H2	119.2	C11—C12—H12	121.7
C1—C2—H2	119.2	C12—C13—C14	122.3 (2)
C2—C3—C4	117.78 (16)	C12—C13—H13	118.8
C2—C3—C18	121.49 (17)	C14—C13—H13	118.8
C4—C3—C18	120.73 (17)	C15—C14—C13	121.7 (2)
C5—C4—C3	121.26 (16)	C15—C14—H14	119.1
C5—C4—H4	119.4	C13—C14—H14	119.1
C3—C4—H4	119.4	C14—C15—C10	115.9 (2)
C4—C5—C6	120.72 (16)	C14—C15—H15	122.1
C4—C5—H5	119.6	C10—C15—H15	122.1
C6—C5—H5	119.6	N6—C16—N4	111.27 (17)
C1—C6—C5	118.44 (15)	N6—C16—H16	124.4
C1—C6—C7	123.52 (15)	N4—C16—H16	124.4
C5—C6—C7	117.98 (15)	N5—C17—N6	115.75 (16)
O1—C7—C6	121.60 (15)	N5—C17—H17	122.1
O1—C7—C8	118.62 (14)	N6—C17—H17	122.1
C6—C7—C8	119.77 (13)	C3—C18—H18A	109.5
N4—C8—C9	111.15 (13)	C3—C18—H18B	109.5
N4—C8—C7	108.82 (12)	H18A—C18—H18B	109.5
C9—C8—C7	109.71 (13)	C3—C18—H18C	109.5
N4—C8—H8	109.0	H18A—C18—H18C	109.5
C9—C8—H8	109.0	H18B—C18—H18C	109.5
C7—C8—H8	109.0
C10—N1—N2—N3	−0.41 (18)	N2—N1—C9—C8	77.19 (19)
C9—N1—N2—N3	−178.13 (14)	C10—N1—C9—C8	−100.04 (19)
N1—N2—N3—C11	0.04 (19)	N4—C8—C9—N1	48.48 (19)
C16—N4—N5—C17	−0.75 (18)	C7—C8—C9—N1	168.88 (14)
C8—N4—N5—C17	−175.69 (14)	N2—N1—C10—C11	0.59 (17)
C6—C1—C2—C3	−1.7 (3)	C9—N1—C10—C11	178.04 (15)
C1—C2—C3—C4	0.2 (3)	N2—N1—C10—C15	−179.77 (18)
C1—C2—C3—C18	−179.91 (19)	C9—N1—C10—C15	−2.3 (3)
C2—C3—C4—C5	1.1 (3)	N2—N3—C11—C10	0.33 (19)
C18—C3—C4—C5	−178.80 (19)	N2—N3—C11—C12	179.39 (17)
C3—C4—C5—C6	−0.8 (3)	N1—C10—C11—N3	−0.56 (18)
C2—C1—C6—C5	2.0 (3)	C15—C10—C11—N3	179.76 (16)
C2—C1—C6—C7	−175.08 (17)	N1—C10—C11—C12	−179.71 (16)
C4—C5—C6—C1	−0.7 (3)	C15—C10—C11—C12	0.6 (3)
C4—C5—C6—C7	176.51 (16)	N3—C11—C12—C13	−178.94 (19)
C1—C6—C7—O1	153.71 (18)	C10—C11—C12—C13	0.0 (3)
C5—C6—C7—O1	−23.4 (2)	C11—C12—C13—C14	−0.6 (3)
C1—C6—C7—C8	−27.3 (2)	C12—C13—C14—C15	0.7 (4)
C5—C6—C7—C8	155.59 (15)	C13—C14—C15—C10	−0.1 (3)
C16—N4—C8—C9	−104.4 (2)	N1—C10—C15—C14	179.87 (18)
N5—N4—C8—C9	69.33 (17)	C11—C10—C15—C14	−0.5 (3)
C16—N4—C8—C7	134.70 (18)	C17—N6—C16—N4	−0.4 (2)
N5—N4—C8—C7	−51.59 (17)	N5—N4—C16—N6	0.7 (2)
O1—C7—C8—N4	115.58 (17)	C8—N4—C16—N6	174.99 (16)
C6—C7—C8—N4	−63.41 (18)	N4—N5—C17—N6	0.5 (2)
O1—C7—C8—C9	−6.2 (2)	C16—N6—C17—N5	−0.1 (2)
C6—C7—C8—C9	174.79 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N6^i	0.93	2.55	3.418 (3)	155
C16—H16···N2^ii	0.93	2.44	3.328 (3)	159
C17—H17···O1^iii	0.93	2.47	3.237 (3)	140

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) x, −y+1, z+1/2.