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In the title compound, C17H13ClN6O, mol­ecules are linked into a zigzag chain along the b axis by C—H...N hydrogen bonds. The packing is further stabilized by π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031564/at2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031564/at2077Isup2.hkl
Contains datablock I

CCDC reference: 620531

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.62 su PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. N5 .. 3.28 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C17 H13 Cl N6 O
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 4 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(Benzotriazol-1-yl)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)propan-1-one top
Crystal data top
C17H13ClN6OF(000) = 1456
Mr = 352.78Dx = 1.430 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2673 reflections
a = 29.914 (7) Åθ = 2.8–25.3°
b = 8.1198 (18) ŵ = 0.25 mm1
c = 14.818 (3) ÅT = 293 K
β = 114.462 (3)°Block, colourless
V = 3276.2 (13) Å30.23 × 0.23 × 0.19 mm
Z = 8
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3216 independent reflections
Radiation source: fine-focus sealed tube2506 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.5°
ω scansh = 3136
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 108
Tmin = 0.944, Tmax = 0.954l = 1815
8830 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0491P)2 + 1.1575P]
where P = (Fo2 + 2Fc2)/3
3216 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 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
Cl10.01958 (2)0.71656 (7)0.39583 (5)0.0761 (2)
O10.08426 (5)1.45486 (17)0.29459 (9)0.0623 (4)
N10.20601 (5)1.53651 (17)0.03970 (10)0.0407 (3)
N20.25021 (5)1.46678 (19)0.01523 (11)0.0482 (4)
N30.27892 (5)1.50839 (19)0.07542 (12)0.0522 (4)
N40.12956 (5)1.30862 (16)0.06412 (9)0.0358 (3)
N50.09285 (5)1.39659 (18)0.05559 (11)0.0466 (4)
N60.12947 (6)1.2325 (2)0.07676 (12)0.0694 (5)
C10.08977 (6)1.0213 (2)0.24358 (13)0.0461 (4)
H1A0.12171.01330.19510.055*
C20.06277 (7)0.8802 (2)0.28091 (14)0.0540 (5)
H2B0.07660.77720.25890.065*
C30.01521 (7)0.8933 (2)0.35101 (14)0.0509 (5)
C40.00573 (7)1.0441 (2)0.38537 (14)0.0554 (5)
H4A0.03801.05120.43270.066*
C50.02152 (6)1.1842 (2)0.34904 (13)0.0497 (5)
H5B0.00761.28670.37230.060*
C60.06973 (6)1.1747 (2)0.27769 (11)0.0381 (4)
C70.09716 (6)1.3309 (2)0.24506 (12)0.0401 (4)
C80.14310 (6)1.3397 (2)0.14584 (11)0.0376 (4)
H8A0.16651.25530.14570.045*
C90.16679 (6)1.5089 (2)0.13680 (13)0.0479 (4)
H9A0.17981.51890.18660.057*
H9B0.14191.59320.14980.057*
C100.25287 (7)1.6073 (2)0.11116 (12)0.0448 (4)
C110.20566 (6)1.6258 (2)0.03794 (13)0.0420 (4)
C120.17004 (8)1.7194 (2)0.05204 (17)0.0618 (6)
H12A0.13841.73210.00280.074*
C130.18487 (11)1.7918 (3)0.1437 (2)0.0809 (8)
H13A0.16261.85620.15690.097*
C140.23251 (12)1.7718 (3)0.21820 (19)0.0804 (8)
H14A0.24061.82240.27930.097*
C150.26696 (9)1.6817 (3)0.20411 (15)0.0647 (6)
H15A0.29851.66970.25370.078*
C160.15057 (7)1.2146 (3)0.01578 (14)0.0591 (5)
H16A0.17701.14470.02690.071*
C170.09469 (7)1.3454 (3)0.02991 (13)0.0524 (5)
H17A0.07341.38460.05630.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0609 (3)0.0565 (3)0.0964 (4)0.0164 (2)0.0180 (3)0.0239 (3)
O10.0676 (9)0.0501 (8)0.0484 (7)0.0073 (7)0.0031 (6)0.0134 (6)
N10.0364 (7)0.0382 (8)0.0445 (8)0.0029 (6)0.0136 (6)0.0021 (6)
N20.0406 (8)0.0468 (9)0.0544 (9)0.0024 (7)0.0169 (7)0.0024 (7)
N30.0429 (8)0.0481 (9)0.0556 (9)0.0016 (7)0.0104 (7)0.0001 (7)
N40.0335 (7)0.0377 (8)0.0343 (7)0.0023 (6)0.0123 (6)0.0003 (6)
N50.0408 (8)0.0485 (9)0.0508 (9)0.0067 (7)0.0190 (7)0.0016 (7)
N60.0622 (11)0.1054 (15)0.0455 (9)0.0216 (10)0.0272 (8)0.0195 (10)
C10.0346 (9)0.0464 (10)0.0489 (10)0.0028 (8)0.0089 (7)0.0026 (8)
C20.0478 (10)0.0396 (10)0.0670 (12)0.0031 (8)0.0162 (9)0.0034 (9)
C30.0450 (10)0.0497 (11)0.0540 (11)0.0080 (9)0.0166 (8)0.0136 (9)
C40.0387 (9)0.0594 (13)0.0532 (11)0.0030 (9)0.0041 (8)0.0044 (9)
C50.0430 (10)0.0471 (11)0.0475 (10)0.0029 (8)0.0072 (8)0.0031 (8)
C60.0371 (8)0.0430 (9)0.0336 (8)0.0008 (7)0.0139 (7)0.0000 (7)
C70.0415 (9)0.0425 (10)0.0340 (8)0.0002 (8)0.0134 (7)0.0037 (8)
C80.0365 (8)0.0377 (9)0.0360 (8)0.0007 (7)0.0125 (7)0.0015 (7)
C90.0464 (10)0.0465 (11)0.0421 (9)0.0090 (8)0.0098 (8)0.0028 (8)
C100.0522 (10)0.0341 (9)0.0439 (10)0.0085 (8)0.0158 (8)0.0005 (7)
C110.0454 (9)0.0314 (9)0.0511 (10)0.0059 (7)0.0220 (8)0.0020 (8)
C120.0589 (12)0.0475 (12)0.0892 (16)0.0012 (9)0.0409 (12)0.0059 (11)
C130.113 (2)0.0512 (13)0.114 (2)0.0050 (13)0.0831 (19)0.0173 (14)
C140.128 (2)0.0557 (14)0.0675 (15)0.0200 (15)0.0506 (17)0.0184 (12)
C150.0885 (16)0.0470 (12)0.0502 (11)0.0176 (11)0.0203 (11)0.0057 (9)
C160.0533 (11)0.0770 (14)0.0479 (11)0.0258 (10)0.0220 (9)0.0224 (10)
C170.0435 (10)0.0698 (13)0.0461 (10)0.0008 (9)0.0207 (9)0.0110 (10)
Geometric parameters (Å, º) top
Cl1—C31.7352 (19)C5—C61.393 (2)
O1—C71.211 (2)C5—H5B0.9300
N1—N21.3430 (19)C6—C71.479 (2)
N1—C111.364 (2)C7—C81.543 (2)
N1—C91.449 (2)C8—C91.526 (2)
N2—N31.304 (2)C8—H8A0.9800
N3—C101.369 (2)C9—H9A0.9700
N4—C161.328 (2)C9—H9B0.9700
N4—N51.3593 (19)C10—C111.388 (2)
N4—C81.449 (2)C10—C151.400 (3)
N5—C171.312 (2)C11—C121.393 (3)
N6—C161.307 (2)C12—C131.374 (3)
N6—C171.344 (3)C12—H12A0.9300
C1—C21.379 (2)C13—C141.405 (4)
C1—C61.384 (2)C13—H13A0.9300
C1—H1A0.9300C14—C151.349 (4)
C2—C31.375 (3)C14—H14A0.9300
C2—H2B0.9300C15—H15A0.9300
C3—C41.374 (3)C16—H16A0.9300
C4—C51.373 (3)C17—H17A0.9300
C4—H4A0.9300
N2—N1—C11110.31 (14)N4—C8—H8A108.9
N2—N1—C9120.30 (14)C9—C8—H8A108.9
C11—N1—C9129.38 (15)C7—C8—H8A108.9
N3—N2—N1108.88 (14)N1—C9—C8112.47 (14)
N2—N3—C10108.24 (14)N1—C9—H9A109.1
C16—N4—N5108.75 (14)C8—C9—H9A109.1
C16—N4—C8130.72 (14)N1—C9—H9B109.1
N5—N4—C8120.16 (13)C8—C9—H9B109.1
C17—N5—N4102.17 (14)H9A—C9—H9B107.8
C16—N6—C17102.18 (16)N3—C10—C11108.62 (15)
C2—C1—C6120.54 (16)N3—C10—C15130.26 (18)
C2—C1—H1A119.7C11—C10—C15121.12 (19)
C6—C1—H1A119.7N1—C11—C10103.96 (15)
C3—C2—C1119.33 (17)N1—C11—C12133.64 (17)
C3—C2—H2B120.3C10—C11—C12122.41 (18)
C1—C2—H2B120.3C13—C12—C11115.3 (2)
C4—C3—C2121.29 (17)C13—C12—H12A122.3
C4—C3—Cl1119.10 (14)C11—C12—H12A122.3
C2—C3—Cl1119.61 (15)C12—C13—C14122.3 (2)
C5—C4—C3119.20 (17)C12—C13—H13A118.8
C5—C4—H4A120.4C14—C13—H13A118.8
C3—C4—H4A120.4C15—C14—C13122.2 (2)
C4—C5—C6120.74 (17)C15—C14—H14A118.9
C4—C5—H5B119.6C13—C14—H14A118.9
C6—C5—H5B119.6C14—C15—C10116.7 (2)
C1—C6—C5118.89 (16)C14—C15—H15A121.7
C1—C6—C7123.70 (15)C10—C15—H15A121.7
C5—C6—C7117.38 (15)N6—C16—N4111.52 (17)
O1—C7—C6121.36 (15)N6—C16—H16A124.2
O1—C7—C8118.27 (15)N4—C16—H16A124.2
C6—C7—C8120.37 (14)N5—C17—N6115.38 (17)
N4—C8—C9111.33 (13)N5—C17—H17A122.3
N4—C8—C7109.96 (13)N6—C17—H17A122.3
C9—C8—C7108.86 (13)
C11—N1—N2—N30.49 (19)N2—N1—C9—C877.0 (2)
C9—N1—N2—N3179.44 (14)C11—N1—C9—C8101.7 (2)
N1—N2—N3—C100.14 (19)N4—C8—C9—N150.24 (19)
C16—N4—N5—C170.65 (19)C7—C8—C9—N1171.61 (14)
C8—N4—N5—C17174.37 (14)N2—N3—C10—C110.2 (2)
C6—C1—C2—C31.4 (3)N2—N3—C10—C15179.26 (18)
C1—C2—C3—C40.8 (3)N2—N1—C11—C100.62 (18)
C1—C2—C3—Cl1178.22 (15)C9—N1—C11—C10179.44 (15)
C2—C3—C4—C50.2 (3)N2—N1—C11—C12179.57 (19)
Cl1—C3—C4—C5179.14 (15)C9—N1—C11—C120.7 (3)
C3—C4—C5—C60.4 (3)N3—C10—C11—N10.52 (18)
C2—C1—C6—C51.2 (3)C15—C10—C11—N1179.64 (16)
C2—C1—C6—C7176.78 (17)N3—C10—C11—C12179.64 (17)
C4—C5—C6—C10.2 (3)C15—C10—C11—C120.5 (3)
C4—C5—C6—C7177.85 (17)N1—C11—C12—C13179.99 (19)
C1—C6—C7—O1158.71 (18)C10—C11—C12—C130.2 (3)
C5—C6—C7—O119.3 (2)C11—C12—C13—C140.4 (3)
C1—C6—C7—C821.7 (2)C12—C13—C14—C150.8 (4)
C5—C6—C7—C8160.33 (15)C13—C14—C15—C100.4 (3)
C16—N4—C8—C9104.0 (2)N3—C10—C15—C14179.1 (2)
N5—N4—C8—C968.13 (18)C11—C10—C15—C140.2 (3)
C16—N4—C8—C7135.26 (19)C17—N6—C16—N40.9 (2)
N5—N4—C8—C752.60 (18)N5—N4—C16—N61.0 (2)
O1—C7—C8—N4115.81 (17)C8—N4—C16—N6173.87 (17)
C6—C7—C8—N463.82 (19)N4—N5—C17—N60.1 (2)
O1—C7—C8—C96.4 (2)C16—N6—C17—N50.5 (3)
C6—C7—C8—C9173.98 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···N6i0.932.593.461 (3)155
C16—H16A···N2ii0.932.433.316 (3)159
C17—H17A···O1iii0.932.473.188 (3)134
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1/2, y+5/2, z; (iii) x, y+3, z1/2.
 

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