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The structure of C17H16N4 contains no hydrogen bonds either strong or weak. The only molecular interaction is π–π stacking between the benzotriazole groups in which the perpendicular distance between the triazole group and the benzene group is 3.695 (1) Å, with a distance of 3.822(2) Å between their centroids.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001672/na6042sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001672/na6042Isup2.hkl
Contains datablock I

CCDC reference: 159760

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.112
  • Data-to-parameter ratio = 16.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

The title compound, (I), was obtained as a by-product in the preparation of tricyclic heterocycles by annelation using benzotriazole as a synthetic auxiliary (Katritzky et al., 1998). Derivatives of the tricyclic system 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline, known as lilolidine (Katayama et al., 1985), i.e. pyroquilone (Bass et al., 1981; Muecke & Gross, 1986; Nakamura, 1986) and analogues (Bass et al., 1975a,b, 1976) have shown antifungal applications in rice crops.

Table 1 lists the geometric parameters, while Fig. 1 shows a view of the molecule. The only molecular interaction is ππ stacking between the benzotriazole groups in which the perpendicular distance between the triazole group at (x, y, z) and the benzene group at (-x, -y, -z) is 3.695 (1) Å, with a distance of 3.822 (2) Å between their centroids (Fig. 2). Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.

Experimental top

Anhydrous ZnBr2 (50 mg) was added to a mixture of 1-(indolin-1-ylmethyl)benzotriazole (1.99 mmol) and dodecyl vinyl ether (4 mmol) in dry tetrahydrofuran (20 ml) and then stirred at room temperature for 3 h. The solvent was removed under vacuum and the residue was separated by column chromatography (gradient: hexane/ethyl acetate) affording, in addition to the expected compound 6-dodecyloxy-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (210 mg), the title compound as a by-product (160 mg, m.p. 422–423 K). Compound (I) crystallized directly from the chromatographic solvents (hexane/ethyl acetate 3:2), affording crystals suitable for X-ray diffraction.

Refinement top

H atoms were treated as riding, with C—H distances in the range 0.95–1.00 Å.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the crystal structure.
6-(1H-1,2,3-Benzotriazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline top
Crystal data top
C17H16N4Dx = 1.334 Mg m3
Mr = 275.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 5825 reflections
a = 10.7112 (3) Åθ = 1.0–27.5°
b = 10.8297 (3) ŵ = 0.08 mm1
c = 23.6321 (5) ÅT = 150 K
V = 2741.56 (12) Å3Block, red
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 1168
Data collection top
KappaCCD
diffractometer
3083 independent reflections
Radiation source: fine-focus sealed X-ray tube2317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ϕ and ω scans with κ offsetsθmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1313
Tmin = 0.976, Tmax = 0.984k = 1314
10806 measured reflectionsl = 2729
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.27 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
3083 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C17H16N4V = 2741.56 (12) Å3
Mr = 275.35Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.7112 (3) ŵ = 0.08 mm1
b = 10.8297 (3) ÅT = 150 K
c = 23.6321 (5) Å0.30 × 0.20 × 0.20 mm
Data collection top
KappaCCD
diffractometer
3083 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
2317 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.984Rint = 0.077
10806 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.27Δρmax = 0.17 e Å3
3083 reflectionsΔρmin = 0.22 e Å3
190 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. no transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.52393 (14)0.00297 (12)0.23920 (6)0.0396 (3)
C20.57262 (13)0.01163 (13)0.17862 (6)0.0402 (3)
N30.46252 (11)0.01106 (9)0.14332 (4)0.0322 (3)
C40.47813 (13)0.04207 (11)0.08388 (5)0.0330 (3)
C50.35003 (12)0.06262 (11)0.05862 (5)0.0326 (3)
C60.28081 (12)0.16998 (10)0.08674 (5)0.0305 (3)
C6A0.29648 (12)0.16893 (10)0.15056 (5)0.0291 (3)
C70.23095 (13)0.24471 (11)0.18800 (5)0.0349 (3)
C80.25715 (14)0.24317 (11)0.24530 (5)0.0396 (3)
C9A0.41727 (13)0.09237 (11)0.23103 (5)0.0340 (3)
C90.35090 (14)0.16726 (12)0.26727 (5)0.0388 (3)
C10B0.38753 (12)0.09318 (10)0.17352 (5)0.0298 (3)
N610.14927 (10)0.16840 (8)0.07061 (4)0.0314 (3)
N620.10258 (12)0.25838 (10)0.03668 (5)0.0398 (3)
N630.01431 (12)0.23478 (10)0.02593 (5)0.0433 (3)
C63A0.04553 (13)0.12619 (12)0.05275 (5)0.0349 (3)
C640.15776 (13)0.06061 (13)0.05325 (6)0.0412 (3)
C650.15915 (14)0.04872 (13)0.08263 (6)0.0432 (4)
C660.05330 (14)0.09096 (12)0.11197 (5)0.0390 (3)
C670.05720 (13)0.02748 (11)0.11262 (5)0.0334 (3)
C67A0.05891 (12)0.08272 (11)0.08148 (5)0.0299 (3)
H1A0.49440.07680.25470.047*
H1B0.58870.03760.26450.047*
H2A0.63920.04920.17050.048*
H2B0.60580.09580.17230.048*
H4A0.52120.02600.06390.040*
H4B0.52920.11780.08000.040*
H5A0.30000.01370.06290.039*
H5B0.35870.07970.01770.039*
H60.31800.24850.07220.037*
H70.16760.29790.17400.042*
H80.21070.29460.27010.047*
H90.36860.16730.30670.047*
H640.22980.09030.03420.049*
H650.23330.09690.08310.052*
H660.05870.16660.13220.047*
H670.12810.05620.13290.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0401 (9)0.0424 (8)0.0361 (7)0.0012 (6)0.0053 (6)0.0044 (6)
C20.0373 (8)0.0404 (7)0.0428 (7)0.0045 (6)0.0045 (6)0.0041 (6)
N30.0345 (7)0.0308 (6)0.0312 (5)0.0026 (5)0.0004 (4)0.0008 (4)
C40.0340 (7)0.0313 (7)0.0337 (7)0.0013 (5)0.0037 (5)0.0015 (5)
C50.0367 (8)0.0310 (7)0.0301 (6)0.0031 (6)0.0019 (5)0.0014 (5)
C60.0330 (7)0.0250 (6)0.0336 (7)0.0038 (5)0.0017 (5)0.0018 (5)
C6A0.0307 (7)0.0246 (6)0.0318 (6)0.0061 (5)0.0004 (5)0.0004 (5)
C70.0342 (7)0.0306 (7)0.0399 (7)0.0014 (5)0.0005 (6)0.0034 (5)
C80.0396 (8)0.0405 (8)0.0386 (7)0.0029 (7)0.0055 (6)0.0110 (6)
C9A0.0364 (8)0.0335 (7)0.0323 (7)0.0071 (6)0.0020 (5)0.0017 (5)
C90.0431 (9)0.0431 (8)0.0303 (7)0.0076 (6)0.0013 (6)0.0038 (6)
C10B0.0317 (7)0.0250 (6)0.0327 (6)0.0063 (5)0.0010 (5)0.0012 (5)
N610.0363 (7)0.0252 (5)0.0327 (6)0.0008 (5)0.0050 (4)0.0016 (4)
N620.0487 (8)0.0300 (6)0.0408 (6)0.0047 (5)0.0106 (5)0.0056 (5)
N630.0459 (8)0.0360 (6)0.0481 (7)0.0044 (5)0.0115 (6)0.0029 (5)
C63A0.0385 (8)0.0325 (7)0.0338 (7)0.0058 (6)0.0051 (6)0.0049 (5)
C640.0325 (8)0.0489 (8)0.0421 (8)0.0050 (7)0.0048 (6)0.0086 (6)
C650.0354 (9)0.0479 (8)0.0464 (8)0.0066 (7)0.0034 (6)0.0089 (6)
C660.0432 (9)0.0336 (7)0.0402 (7)0.0030 (6)0.0075 (6)0.0019 (6)
C670.0371 (8)0.0307 (7)0.0325 (7)0.0023 (6)0.0011 (5)0.0001 (5)
C67A0.0322 (7)0.0288 (6)0.0287 (6)0.0000 (5)0.0000 (5)0.0046 (5)
Geometric parameters (Å, º) top
C1—C9A1.510 (2)C9A—C91.3773 (19)
C1—C21.5317 (19)C9A—C10B1.3959 (17)
C2—N31.4654 (17)N61—N621.3575 (14)
N3—C10B1.3948 (16)N61—C67A1.3652 (16)
N3—C41.4539 (16)N62—N631.3028 (16)
C4—C51.5128 (18)N63—C63A1.3771 (18)
C5—C61.5308 (17)C63A—C67A1.3908 (18)
C6—N611.4598 (16)C63A—C641.396 (2)
C6—C6A1.5175 (17)C64—C651.373 (2)
C6A—C10B1.3851 (17)C65—C661.406 (2)
C6A—C71.3960 (17)C66—C671.3688 (19)
C7—C81.3832 (18)C67—C67A1.4023 (17)
C8—C91.3977 (19)
C9A—C1—C2101.79 (10)C6A—C10B—N3125.63 (11)
N3—C2—C1103.93 (11)C6A—C10B—C9A123.08 (11)
C10B—N3—C4114.42 (10)N3—C10B—C9A111.27 (11)
C10B—N3—C2106.20 (10)N62—N61—C67A109.75 (11)
C4—N3—C2119.75 (11)N62—N61—C6120.10 (10)
N3—C4—C5108.11 (10)C67A—N61—C6130.02 (10)
C4—C5—C6112.32 (10)N63—N62—N61109.17 (10)
N61—C6—C6A111.48 (10)N62—N63—C63A108.13 (10)
N61—C6—C5110.19 (10)N63—C63A—C67A108.57 (12)
C6A—C6—C5111.85 (10)N63—C63A—C64130.34 (12)
C10B—C6A—C7117.00 (11)C67A—C63A—C64121.08 (12)
C10B—C6A—C6118.14 (11)C65—C64—C63A116.90 (13)
C7—C6A—C6124.73 (11)C64—C65—C66121.44 (13)
C8—C7—C6A120.75 (12)C67—C66—C65122.66 (13)
C7—C8—C9121.10 (12)C66—C67—C67A115.65 (12)
C9—C9A—C10B118.94 (12)N61—C67A—C63A104.38 (10)
C9—C9A—C1133.53 (12)N61—C67A—C67133.36 (12)
C10B—C9A—C1107.53 (11)C63A—C67A—C67122.26 (12)
C9A—C9—C8119.10 (12)
C9A—C1—C2—N328.06 (13)C9—C9A—C10B—C6A2.08 (19)
C1—C2—N3—C10B29.98 (13)C1—C9A—C10B—C6A177.46 (11)
C1—C2—N3—C4161.43 (10)C9—C9A—C10B—N3179.20 (11)
C10B—N3—C4—C551.17 (13)C1—C9A—C10B—N31.26 (14)
C2—N3—C4—C5178.93 (10)C6A—C6—N61—N62123.94 (11)
N3—C4—C5—C661.63 (13)C5—C6—N61—N62111.24 (11)
C4—C5—C6—N61166.92 (10)C6A—C6—N61—C67A60.65 (15)
C4—C5—C6—C6A42.32 (14)C5—C6—N61—C67A64.16 (15)
N61—C6—C6A—C10B137.22 (11)C67A—N61—N62—N630.79 (14)
C5—C6—C6A—C10B13.34 (15)C6—N61—N62—N63177.05 (10)
N61—C6—C6A—C746.99 (15)N61—N62—N63—C63A0.67 (14)
C5—C6—C6A—C7170.87 (11)N62—N63—C63A—C67A0.32 (14)
C10B—C6A—C7—C80.11 (18)N62—N63—C63A—C64178.31 (13)
C6—C6A—C7—C8175.72 (12)N63—C63A—C64—C65177.62 (13)
C6A—C7—C8—C90.9 (2)C67A—C63A—C64—C650.86 (19)
C2—C1—C9A—C9162.53 (14)C63A—C64—C65—C661.5 (2)
C2—C1—C9A—C10B16.91 (14)C64—C65—C66—C670.8 (2)
C10B—C9A—C9—C80.98 (19)C65—C66—C67—C67A0.63 (18)
C1—C9A—C9—C8178.41 (14)N62—N61—C67A—C63A0.56 (13)
C7—C8—C9—C9A0.5 (2)C6—N61—C67A—C63A176.33 (11)
C7—C6A—C10B—N3179.84 (11)N62—N61—C67A—C67178.88 (12)
C6—C6A—C10B—N34.04 (18)C6—N61—C67A—C673.1 (2)
C7—C6A—C10B—C9A1.62 (18)N63—C63A—C67A—N610.15 (13)
C6—C6A—C10B—C9A174.49 (11)C64—C63A—C67A—N61178.93 (11)
C4—N3—C10B—C6A24.18 (18)N63—C63A—C67A—C67179.37 (11)
C2—N3—C10B—C6A158.56 (12)C64—C63A—C67A—C670.59 (19)
C4—N3—C10B—C9A154.50 (11)C66—C67—C67A—N61178.05 (13)
C2—N3—C10B—C9A20.12 (14)C66—C67—C67A—C63A1.31 (18)

Experimental details

Crystal data
Chemical formulaC17H16N4
Mr275.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)10.7112 (3), 10.8297 (3), 23.6321 (5)
V3)2741.56 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.976, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
10806, 3083, 2317
Rint0.077
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.112, 1.27
No. of reflections3083
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.22

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
C2—N31.4654 (17)N61—N621.3575 (14)
N3—C10B1.3948 (16)N61—C67A1.3652 (16)
N3—C41.4539 (16)N62—N631.3028 (16)
C6—N611.4598 (16)N63—C63A1.3771 (18)
C10B—N3—C4114.42 (10)N62—N61—C6120.10 (10)
C10B—N3—C2106.20 (10)C67A—N61—C6130.02 (10)
C4—N3—C2119.75 (11)N63—N62—N61109.17 (10)
N62—N61—C67A109.75 (11)N62—N63—C63A108.13 (10)
 

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