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In the mol­ecule of the title compound, C16H15N3O, the benzotriazole system is planar. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains. The packing is further stabilized by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603025X/hk2099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603025X/hk2099Isup2.hkl
Contains datablock I

CCDC reference: 621361

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.055
  • wR factor = 0.138
  • Data-to-parameter ratio = 8.2

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 N3 - C11 .. 6.25 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C16 .. 5.93 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C16 H15 N3 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.07 From the CIF: _reflns_number_total 1492 Count of symmetry unique reflns 1512 Completeness (_total/calc) 98.68% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 2 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(Benzotriazol-1-yl)-1-p-tolylpropan-1-one top
Crystal data top
C16H15N3OF(000) = 280
Mr = 265.31Dx = 1.279 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 735 reflections
a = 11.565 (4) Åθ = 3.4–19.5°
b = 5.7481 (18) ŵ = 0.08 mm1
c = 11.666 (4) ÅT = 294 K
β = 117.309 (5)°Needle, colorless
V = 689.1 (4) Å30.47 × 0.11 × 0.08 mm
Z = 2
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1492 independent reflections
Radiation source: fine-focus sealed tube1031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.0°
ω scansh = 1413
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 76
Tmin = 0.962, Tmax = 0.993l = 1411
3769 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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1105P]
where P = (Fo2 + 2Fc2)/3
1492 reflections(Δ/σ)max = 0.020
181 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.11 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
O10.7827 (3)0.2083 (8)0.1156 (3)0.1000 (13)
N10.3740 (4)0.4690 (7)0.3124 (5)0.0876 (13)
N20.4561 (4)0.3445 (7)0.2126 (4)0.0834 (12)
N30.4778 (3)0.1449 (6)0.2598 (4)0.0686 (10)
C10.7787 (4)0.3857 (9)0.1790 (4)0.0674 (11)
H1A0.72010.27840.18240.081*
C20.8339 (4)0.5445 (9)0.2745 (4)0.0688 (12)
H2A0.81190.54330.34180.083*
C30.9220 (4)0.7091 (8)0.2756 (4)0.0682 (12)
C40.9554 (4)0.7010 (9)0.1753 (4)0.0783 (14)
H4A1.01640.80500.17410.094*
C50.8987 (4)0.5401 (9)0.0781 (4)0.0776 (14)
H5A0.92160.53820.01140.093*
C60.8077 (4)0.3798 (8)0.0768 (4)0.0644 (11)
C70.7486 (4)0.2147 (9)0.0307 (4)0.0710 (12)
C80.6443 (4)0.0513 (9)0.0374 (4)0.0753 (12)
H8A0.68490.07960.01950.090*
H8B0.59010.13120.00660.090*
C90.5603 (4)0.0379 (9)0.1703 (4)0.0743 (12)
H9A0.61520.10510.20430.089*
H9B0.50490.16050.16590.089*
C100.3427 (4)0.3503 (7)0.4240 (5)0.0665 (11)
C110.4102 (4)0.1389 (8)0.3905 (4)0.0593 (10)
C120.3990 (4)0.0241 (8)0.4837 (4)0.0669 (11)
H12A0.44400.16440.46150.080*
C130.3196 (4)0.0316 (9)0.6074 (5)0.0760 (13)
H13A0.31100.07290.67170.091*
C140.2504 (4)0.2381 (10)0.6429 (5)0.0822 (14)
H14A0.19560.26660.72970.099*
C150.2607 (4)0.4011 (9)0.5532 (5)0.0778 (13)
H15A0.21480.54040.57740.093*
C160.9804 (5)0.8843 (11)0.3802 (4)0.0994 (17)
H26A0.94700.86230.44110.149*
H26B0.95861.03770.34400.149*
H26C1.07320.86630.42300.149*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.100 (2)0.139 (3)0.084 (2)0.030 (3)0.0616 (18)0.024 (2)
N10.087 (3)0.054 (2)0.127 (4)0.000 (2)0.054 (3)0.021 (3)
N20.085 (3)0.062 (2)0.103 (3)0.001 (2)0.042 (2)0.018 (2)
N30.068 (2)0.053 (2)0.092 (3)0.0047 (19)0.042 (2)0.016 (2)
C10.061 (2)0.079 (3)0.066 (3)0.001 (2)0.033 (2)0.010 (3)
C20.061 (2)0.091 (3)0.063 (2)0.003 (3)0.036 (2)0.001 (3)
C30.062 (2)0.070 (3)0.058 (2)0.010 (2)0.015 (2)0.003 (2)
C40.070 (3)0.091 (4)0.077 (3)0.017 (3)0.036 (2)0.006 (3)
C50.070 (3)0.100 (4)0.071 (3)0.012 (3)0.039 (2)0.004 (3)
C60.055 (2)0.080 (3)0.061 (2)0.000 (2)0.0286 (19)0.005 (2)
C70.060 (2)0.085 (3)0.069 (3)0.003 (3)0.031 (2)0.002 (3)
C80.078 (3)0.069 (3)0.081 (3)0.006 (3)0.038 (2)0.002 (3)
C90.071 (3)0.063 (3)0.084 (3)0.001 (3)0.031 (2)0.000 (3)
C100.060 (2)0.047 (2)0.096 (3)0.001 (2)0.040 (2)0.002 (3)
C110.048 (2)0.060 (3)0.070 (3)0.011 (2)0.028 (2)0.003 (2)
C120.066 (2)0.055 (2)0.087 (3)0.001 (2)0.042 (2)0.000 (3)
C130.079 (3)0.077 (4)0.074 (3)0.011 (3)0.037 (3)0.005 (3)
C140.073 (3)0.076 (3)0.097 (3)0.015 (3)0.038 (3)0.008 (3)
C150.061 (3)0.061 (3)0.107 (4)0.003 (2)0.034 (3)0.019 (3)
C160.097 (4)0.094 (4)0.106 (4)0.000 (4)0.045 (3)0.013 (3)
Geometric parameters (Å, º) top
O1—C71.223 (5)C8—C91.493 (6)
N1—N21.325 (5)C8—H8A0.9700
N1—C101.364 (5)C8—H8B0.9700
N2—N31.345 (5)C9—H9A0.9700
N3—C111.357 (5)C9—H9B0.9700
N3—C91.480 (6)C10—C151.394 (6)
C1—C21.352 (6)C10—C111.399 (6)
C1—C61.380 (5)C11—C121.396 (6)
C1—H1A0.9300C12—C131.346 (6)
C2—C31.386 (6)C12—H12A0.9300
C2—H2A0.9300C13—C141.385 (7)
C3—C41.391 (6)C13—H13A0.9300
C3—C161.484 (6)C14—C151.369 (7)
C4—C51.375 (6)C14—H14A0.9300
C4—H4A0.9300C15—H15A0.9300
C5—C61.394 (6)C16—H26A0.9600
C5—H5A0.9300C16—H26B0.9600
C6—C71.467 (6)C16—H26C0.9600
C7—C81.502 (6)
N2—N1—C10109.8 (4)H8A—C8—H8B107.8
N1—N2—N3107.1 (4)N3—C9—C8113.0 (4)
N2—N3—C11111.2 (4)N3—C9—H9A109.0
N2—N3—C9119.8 (4)C8—C9—H9A109.0
C11—N3—C9128.8 (4)N3—C9—H9B109.0
C2—C1—C6121.2 (4)C8—C9—H9B109.0
C2—C1—H1A119.4H9A—C9—H9B107.8
C6—C1—H1A119.4N1—C10—C15132.7 (4)
C1—C2—C3122.4 (4)N1—C10—C11107.3 (4)
C1—C2—H2A118.8C15—C10—C11120.0 (4)
C3—C2—H2A118.8N3—C11—C12133.8 (4)
C2—C3—C4117.1 (4)N3—C11—C10104.6 (4)
C2—C3—C16121.8 (4)C12—C11—C10121.6 (4)
C4—C3—C16121.1 (5)C13—C12—C11116.7 (5)
C5—C4—C3120.3 (4)C13—C12—H12A121.6
C5—C4—H4A119.8C11—C12—H12A121.6
C3—C4—H4A119.8C12—C13—C14122.8 (5)
C4—C5—C6121.7 (4)C12—C13—H13A118.6
C4—C5—H5A119.1C14—C13—H13A118.6
C6—C5—H5A119.1C15—C14—C13121.5 (5)
C1—C6—C5117.1 (4)C15—C14—H14A119.3
C1—C6—C7123.5 (4)C13—C14—H14A119.3
C5—C6—C7119.3 (4)C14—C15—C10117.4 (5)
O1—C7—C6121.0 (4)C14—C15—H15A121.3
O1—C7—C8119.2 (4)C10—C15—H15A121.3
C6—C7—C8119.8 (4)C3—C16—H26A109.5
C9—C8—C7113.2 (4)C3—C16—H26B109.5
C9—C8—H8A108.9H26A—C16—H26B109.5
C7—C8—H8A108.9C3—C16—H26C109.5
C9—C8—H8B108.9H26A—C16—H26C109.5
C7—C8—H8B108.9H26B—C16—H26C109.5
C10—N1—N2—N30.1 (5)C11—N3—C9—C8165.8 (4)
N1—N2—N3—C110.1 (5)C7—C8—C9—N367.9 (5)
N1—N2—N3—C9176.4 (3)N2—N1—C10—C15179.0 (5)
C6—C1—C2—C30.1 (7)N2—N1—C10—C110.0 (5)
C1—C2—C3—C41.9 (6)N2—N3—C11—C12179.9 (4)
C1—C2—C3—C16179.2 (4)C9—N3—C11—C123.8 (7)
C2—C3—C4—C52.2 (7)N2—N3—C11—C100.2 (4)
C16—C3—C4—C5178.9 (4)C9—N3—C11—C10176.0 (4)
C3—C4—C5—C60.6 (7)N1—C10—C11—N30.1 (4)
C2—C1—C6—C51.7 (6)C15—C10—C11—N3179.1 (4)
C2—C1—C6—C7178.7 (4)N1—C10—C11—C12179.9 (4)
C4—C5—C6—C11.4 (7)C15—C10—C11—C120.7 (6)
C4—C5—C6—C7179.0 (4)N3—C11—C12—C13179.5 (4)
C1—C6—C7—O1176.0 (5)C10—C11—C12—C130.3 (6)
C5—C6—C7—O13.6 (7)C11—C12—C13—C140.7 (6)
C1—C6—C7—C84.2 (6)C12—C13—C14—C151.3 (7)
C5—C6—C7—C8176.2 (4)C13—C14—C15—C100.7 (6)
O1—C7—C8—C921.7 (6)N1—C10—C15—C14179.2 (4)
C6—C7—C8—C9158.0 (4)C11—C10—C15—C140.2 (6)
N2—N3—C9—C818.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Cg1i0.932.863.428121
C8—H8A···Cg2ii0.972.993.930165
C12—H12A···Cg3iii0.932.863.534130
C13—H13A···O1iii0.932.543.435 (5)161
Symmetry codes: (i) x+1, y+1/2, z; (ii) x, y1, z; (iii) x+1, y1/2, z1.
 

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