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In the title compound, C16H15N3O2, the dihedral angle between the benzotriazole unit and the other benzene ring is 79.06 (1)°. The crystal structure is stabilized by C—H...π inter­actions and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046654/at2151sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046654/at2151Isup2.hkl
Contains datablock I

CCDC reference: 629409

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

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, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(1H-Benzotriazol-1-yl)-1-(4-methoxyphenyl)propan-1-one top
Crystal data top
C16H15N3O2F(000) = 592
Mr = 281.31Dx = 1.320 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 2043 reflections
a = 10.0442 (17) Åθ = 2.5–25.3°
b = 9.7562 (17) ŵ = 0.09 mm1
c = 14.443 (2) ÅT = 293 K
β = 90.254 (3)°Plate, colourless
V = 1415.3 (4) Å30.25 × 0.19 × 0.05 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area detector
diffractometer
2783 independent reflections
Radiation source: fine-focus sealed tube1979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 1212
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
k = 1212
Tmin = 0.978, Tmax = 0.996l = 1711
7734 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.141P]
where P = (Fo2 + 2Fc2)/3
2783 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.15 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
C60.03114 (14)0.12595 (15)0.12079 (10)0.0497 (4)
C10.03160 (15)0.01709 (16)0.12029 (10)0.0524 (4)
H1A0.11190.06450.11890.063*
O10.26491 (11)0.13480 (12)0.10726 (9)0.0741 (4)
N10.32820 (12)0.41992 (13)0.00474 (10)0.0584 (4)
C70.16168 (15)0.19812 (16)0.11582 (10)0.0542 (4)
C20.08680 (15)0.08802 (16)0.12185 (11)0.0591 (4)
O20.09795 (12)0.22712 (13)0.12033 (10)0.0876 (4)
C150.41170 (14)0.34106 (15)0.04681 (11)0.0541 (4)
C50.08899 (15)0.19570 (17)0.12429 (11)0.0592 (4)
H5A0.09010.29100.12530.071*
C80.16324 (16)0.35242 (17)0.12261 (12)0.0645 (5)
H8A0.13510.37870.18430.077*
H8B0.09890.38920.07900.077*
C100.39872 (15)0.39235 (16)0.13559 (12)0.0598 (4)
C30.20662 (16)0.01712 (19)0.12506 (12)0.0672 (5)
H3A0.28670.06500.12630.081*
C40.20690 (16)0.12305 (19)0.12635 (12)0.0676 (5)
H4A0.28740.17000.12860.081*
N20.26816 (15)0.51443 (14)0.04968 (12)0.0729 (4)
N30.30924 (16)0.49966 (15)0.13462 (12)0.0759 (4)
C90.29770 (17)0.41677 (17)0.10355 (12)0.0686 (5)
H9A0.29860.50960.12760.082*
H9B0.36620.36520.13580.082*
C140.49535 (15)0.23206 (17)0.02544 (13)0.0645 (5)
H14A0.50330.19830.03460.077*
C110.47090 (17)0.3350 (2)0.20846 (13)0.0726 (5)
H11A0.46340.36860.26850.087*
C160.0198 (2)0.30666 (19)0.12294 (15)0.0849 (6)
H16A0.00290.40220.12100.127*
H16B0.06800.28740.17900.127*
H16C0.07420.28430.07060.127*
C130.56525 (17)0.17720 (19)0.09722 (16)0.0749 (5)
H13A0.62270.10430.08580.090*
C120.55298 (18)0.2276 (2)0.18771 (15)0.0789 (6)
H12A0.60190.18690.23480.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0503 (8)0.0535 (9)0.0454 (8)0.0052 (7)0.0007 (6)0.0008 (6)
C10.0479 (8)0.0541 (9)0.0553 (9)0.0068 (7)0.0020 (7)0.0006 (7)
O10.0515 (7)0.0615 (7)0.1092 (10)0.0037 (6)0.0017 (6)0.0002 (6)
N10.0569 (8)0.0468 (7)0.0714 (9)0.0024 (6)0.0034 (7)0.0021 (6)
C70.0540 (9)0.0546 (9)0.0540 (9)0.0036 (7)0.0027 (7)0.0021 (7)
C20.0602 (10)0.0557 (10)0.0616 (10)0.0019 (8)0.0038 (8)0.0002 (7)
O20.0719 (8)0.0554 (8)0.1357 (13)0.0061 (6)0.0078 (7)0.0005 (7)
C150.0457 (8)0.0455 (8)0.0713 (11)0.0068 (7)0.0004 (7)0.0057 (8)
C50.0574 (9)0.0560 (9)0.0642 (11)0.0106 (8)0.0008 (8)0.0021 (7)
C80.0709 (11)0.0553 (10)0.0673 (11)0.0026 (8)0.0133 (8)0.0116 (8)
C100.0539 (9)0.0505 (9)0.0749 (12)0.0064 (7)0.0018 (8)0.0027 (8)
C30.0476 (9)0.0776 (12)0.0763 (12)0.0044 (8)0.0004 (8)0.0033 (9)
C40.0490 (9)0.0784 (12)0.0753 (12)0.0148 (9)0.0003 (8)0.0036 (9)
N20.0729 (10)0.0502 (8)0.0956 (12)0.0069 (7)0.0076 (9)0.0091 (8)
N30.0787 (10)0.0622 (9)0.0869 (12)0.0043 (8)0.0062 (9)0.0144 (8)
C90.0765 (11)0.0552 (10)0.0741 (12)0.0097 (8)0.0007 (9)0.0131 (8)
C140.0487 (9)0.0630 (10)0.0818 (12)0.0023 (8)0.0067 (8)0.0019 (9)
C110.0723 (12)0.0744 (12)0.0713 (12)0.0151 (10)0.0071 (9)0.0032 (9)
C160.0969 (15)0.0560 (11)0.1020 (16)0.0096 (10)0.0056 (12)0.0026 (10)
C130.0529 (10)0.0625 (11)0.1093 (17)0.0044 (8)0.0037 (10)0.0078 (11)
C120.0686 (12)0.0726 (13)0.0957 (16)0.0102 (10)0.0194 (10)0.0226 (11)
Geometric parameters (Å, º) top
C6—C51.3864 (19)C8—H8B0.9700
C6—C11.396 (2)C10—N31.380 (2)
C6—C71.490 (2)C10—C111.397 (2)
C1—C21.376 (2)C3—C41.368 (2)
C1—H1A0.9300C3—H3A0.9300
O1—C71.2137 (17)C4—H4A0.9300
N1—N21.3518 (18)N2—N31.304 (2)
N1—C151.3621 (19)C9—H9A0.9700
N1—C91.461 (2)C9—H9B0.9700
C7—C81.509 (2)C14—C131.364 (3)
C2—O21.3618 (19)C14—H14A0.9300
C2—C31.389 (2)C11—C121.366 (3)
O2—C161.415 (2)C11—H11A0.9300
C15—C101.382 (2)C16—H16A0.9600
C15—C141.389 (2)C16—H16B0.9600
C5—C41.381 (2)C16—H16C0.9600
C5—H5A0.9300C13—C121.401 (3)
C8—C91.516 (2)C13—H13A0.9300
C8—H8A0.9700C12—H12A0.9300
C5—C6—C1119.60 (14)C4—C3—H3A120.0
C5—C6—C7122.41 (14)C2—C3—H3A120.0
C1—C6—C7117.98 (13)C3—C4—C5120.75 (15)
C2—C1—C6119.99 (14)C3—C4—H4A119.6
C2—C1—H1A120.0C5—C4—H4A119.6
C6—C1—H1A120.0N3—N2—N1109.23 (14)
N2—N1—C15109.98 (14)N2—N3—C10107.59 (14)
N2—N1—C9119.16 (14)N1—C9—C8112.15 (13)
C15—N1—C9130.86 (14)N1—C9—H9A109.2
O1—C7—C6121.11 (14)C8—C9—H9A109.2
O1—C7—C8120.39 (15)N1—C9—H9B109.2
C6—C7—C8118.50 (13)C8—C9—H9B109.2
O2—C2—C1124.88 (15)H9A—C9—H9B107.9
O2—C2—C3115.19 (14)C13—C14—C15116.38 (17)
C1—C2—C3119.93 (16)C13—C14—H14A121.8
C2—O2—C16118.52 (14)C15—C14—H14A121.8
N1—C15—C10104.29 (14)C12—C11—C10117.16 (18)
N1—C15—C14133.17 (16)C12—C11—H11A121.4
C10—C15—C14122.54 (15)C10—C11—H11A121.4
C4—C5—C6119.71 (15)O2—C16—H16A109.5
C4—C5—H5A120.1O2—C16—H16B109.5
C6—C5—H5A120.1H16A—C16—H16B109.5
C7—C8—C9114.23 (14)O2—C16—H16C109.5
C7—C8—H8A108.7H16A—C16—H16C109.5
C9—C8—H8A108.7H16B—C16—H16C109.5
C7—C8—H8B108.7C14—C13—C12121.86 (18)
C9—C8—H8B108.7C14—C13—H13A119.1
H8A—C8—H8B107.6C12—C13—H13A119.1
N3—C10—C15108.91 (15)C11—C12—C13121.62 (17)
N3—C10—C11130.65 (17)C11—C12—H12A119.2
C15—C10—C11120.44 (16)C13—C12—H12A119.2
C4—C3—C2120.01 (16)
C5—C6—C1—C21.0 (2)C14—C15—C10—C110.0 (2)
C7—C6—C1—C2177.97 (13)O2—C2—C3—C4179.68 (16)
C5—C6—C7—O1175.57 (15)C1—C2—C3—C40.2 (3)
C1—C6—C7—O13.4 (2)C2—C3—C4—C50.1 (3)
C5—C6—C7—C85.0 (2)C6—C5—C4—C30.1 (3)
C1—C6—C7—C8176.05 (13)C15—N1—N2—N30.17 (17)
C6—C1—C2—O2179.11 (14)C9—N1—N2—N3179.87 (13)
C6—C1—C2—C30.8 (2)N1—N2—N3—C100.01 (18)
C1—C2—O2—C164.0 (3)C15—C10—N3—N20.16 (18)
C3—C2—O2—C16176.08 (16)C11—C10—N3—N2179.94 (17)
N2—N1—C15—C100.26 (16)N2—N1—C9—C876.33 (18)
C9—N1—C15—C10179.91 (14)C15—N1—C9—C8104.05 (18)
N2—N1—C15—C14179.94 (16)C7—C8—C9—N176.65 (19)
C9—N1—C15—C140.3 (3)N1—C15—C14—C13179.83 (15)
C1—C6—C5—C40.6 (2)C10—C15—C14—C130.1 (2)
C7—C6—C5—C4178.28 (14)N3—C10—C11—C12179.93 (17)
O1—C7—C8—C98.6 (2)C15—C10—C11—C120.2 (2)
C6—C7—C8—C9171.95 (13)C15—C14—C13—C120.3 (2)
N1—C15—C10—N30.25 (16)C10—C11—C12—C130.4 (2)
C14—C15—C10—N3179.92 (14)C14—C13—C12—C110.5 (3)
N1—C15—C10—C11179.83 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···Cg3i0.932.913.805162
C9—H9B···Cg3ii0.972.983.663128
Symmetry codes: (i) x, y, z; (ii) x+1, y+1, z.
 

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