Literature DB >> 24109324

5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)meth-yl]-5H-dibenzo[b,f]azepine.

B C Manjunath1, K S Vinay Kumar, S Madan Kumar, M P Sadashiva, N K Lokanath.   

Abstract

In the title compound, C24H20N4, the azepine ring adopts a boat conformation and the dihedral angle between the benzene rings fused to it is 57.95 (8)°. The bond-angle sum at the azepine N atom is 346.6°, indicating a significant deviation from planarity. The triazole ring subtends a dihedral angle of 71.45 (10)° with the terminal phenyl group. A weak intra-molecular C-H⋯Na (a = azepine) inter-action occurs, which closes an S(6) ring.

Entities:  

Year:  2013        PMID： 24109324      PMCID： PMC3793737          DOI： 10.1107/S1600536813018412

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a related structure and background to isoxazole derivatives, see: Abdoh et al. (2013 ▶).

Experimental

Crystal data

C24H20N4 M = 364.44 Monoclinic, a = 9.4394 (10) Å b = 22.206 (3) Å c = 9.4330 (9) Å β = 107.172 (3)° V = 1889.1 (4) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 300 K 0.26 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer 22703 measured reflections 3711 independent reflections 2982 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.124 S = 1.01 3711 reflections 253 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018412/hb7099sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018412/hb7099Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813018412/hb7099Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H20N4F(000) = 768
Mr = 364.44Dx = 1.281 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3711 reflections
a = 9.4394 (10) Åθ = 1.8–26.0°
b = 22.206 (3) ŵ = 0.08 mm−1
c = 9.4330 (9) ÅT = 300 K
β = 107.172 (3)°Block, red
V = 1889.1 (4) Å30.26 × 0.23 × 0.20 mm
Z = 4
Bruker APEXII CCD diffractometerRint = 0.045
Radiation source: graphiteθmax = 26.0°, θmin = 1.8°
φ and ω scansh = −11→11
22703 measured reflectionsk = −27→26
3711 independent reflectionsl = −11→11
2982 reflections with I > 2σ(I)
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) = 0.124H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0634P)2 + 0.445P] where P = (Fo2 + 2Fc2)/3
3711 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
N10.48315 (15)0.41800 (6)0.71285 (15)0.0485 (4)
N20.59240 (19)0.44728 (7)0.81571 (19)0.0671 (6)
N30.68625 (18)0.40672 (9)0.89031 (18)0.0687 (6)
N40.35717 (13)0.32303 (5)0.47460 (12)0.0358 (3)
C10.0910 (2)0.43114 (8)0.5802 (2)0.0602 (6)
C20.22436 (19)0.45366 (6)0.66850 (18)0.0475 (5)
C30.2290 (2)0.48013 (7)0.8030 (2)0.0536 (6)
C40.1028 (2)0.48466 (8)0.8465 (2)0.0605 (6)
C5−0.0294 (2)0.46273 (8)0.7577 (3)0.0667 (7)
C6−0.0358 (2)0.43573 (8)0.6250 (3)0.0690 (7)
C70.3606 (2)0.45281 (7)0.6163 (2)0.0562 (6)
C80.63739 (19)0.35255 (9)0.83410 (18)0.0551 (5)
C90.50799 (17)0.35803 (7)0.72201 (15)0.0410 (4)
C100.40884 (17)0.31033 (7)0.63385 (15)0.0408 (4)
C110.46560 (15)0.33324 (6)0.39878 (15)0.0357 (4)
C120.42678 (17)0.37101 (6)0.27384 (16)0.0404 (4)
C130.5336 (2)0.38298 (7)0.20193 (19)0.0527 (6)
C140.6730 (2)0.35838 (9)0.2500 (2)0.0600 (6)
C150.71005 (19)0.32105 (8)0.3721 (2)0.0553 (6)
C160.60713 (17)0.30859 (7)0.44645 (17)0.0445 (5)
C170.27898 (19)0.39760 (7)0.21582 (17)0.0478 (5)
C180.15052 (19)0.37247 (7)0.21404 (18)0.0484 (5)
C190.13042 (16)0.31254 (7)0.26945 (16)0.0402 (4)
C200.23460 (15)0.28684 (6)0.39198 (14)0.0353 (4)
C210.00604 (17)0.27797 (8)0.19635 (18)0.0523 (5)
C22−0.01154 (19)0.21998 (9)0.2393 (2)0.0582 (6)
C230.0936 (2)0.19481 (8)0.35653 (19)0.0544 (6)
C240.21656 (18)0.22797 (7)0.43327 (17)0.0447 (5)
H10.086300.412800.490300.0720*
H30.318300.494900.864200.0640*
H40.107100.502700.936700.0730*
H5−0.114800.466100.787200.0800*
H6−0.125300.420500.565200.0830*
H7A0.334700.435900.517100.0670*
H7B0.393500.493900.610700.0670*
H80.685000.316300.866900.0660*
H10A0.461800.272300.649400.0490*
H10B0.323500.306000.670300.0490*
H130.509700.408200.119600.0630*
H140.742300.366900.200300.0720*
H150.804300.304200.404600.0660*
H160.632900.283500.529000.0530*
H170.274400.436100.176000.0570*
H180.065400.395200.173700.0580*
H21−0.066400.294700.116800.0630*
H22−0.094800.197900.188600.0700*
H230.082500.155400.384700.0650*
H240.287600.210700.513000.0540*
U11U22U33U12U13U23
N10.0535 (8)0.0486 (7)0.0494 (8)−0.0117 (6)0.0243 (7)−0.0132 (6)
N20.0721 (11)0.0676 (10)0.0667 (10)−0.0319 (8)0.0284 (9)−0.0278 (8)
N30.0584 (9)0.0904 (12)0.0560 (9)−0.0262 (9)0.0148 (8)−0.0203 (9)
N40.0388 (6)0.0403 (6)0.0274 (6)−0.0056 (5)0.0084 (5)−0.0010 (5)
C10.0747 (12)0.0467 (9)0.0548 (10)0.0002 (8)0.0122 (9)−0.0074 (8)
C20.0605 (10)0.0334 (7)0.0510 (9)0.0017 (7)0.0203 (8)−0.0009 (6)
C30.0587 (10)0.0483 (9)0.0551 (10)−0.0030 (7)0.0190 (8)−0.0087 (7)
C40.0681 (12)0.0592 (10)0.0615 (11)0.0058 (9)0.0305 (10)−0.0041 (8)
C50.0601 (12)0.0564 (11)0.0906 (15)0.0077 (9)0.0329 (11)0.0111 (10)
C60.0547 (11)0.0542 (10)0.0881 (15)−0.0045 (8)0.0056 (10)0.0011 (10)
C70.0755 (12)0.0450 (9)0.0562 (10)0.0010 (8)0.0319 (9)−0.0008 (7)
C80.0511 (9)0.0718 (11)0.0393 (8)−0.0110 (8)0.0085 (7)−0.0070 (8)
C90.0454 (8)0.0498 (8)0.0310 (7)−0.0091 (6)0.0164 (6)−0.0051 (6)
C100.0476 (8)0.0450 (8)0.0285 (7)−0.0077 (6)0.0092 (6)−0.0005 (6)
C110.0412 (7)0.0350 (7)0.0309 (7)−0.0060 (5)0.0108 (6)−0.0053 (5)
C120.0506 (8)0.0365 (7)0.0350 (7)−0.0059 (6)0.0139 (7)−0.0016 (6)
C130.0663 (11)0.0538 (9)0.0420 (9)−0.0098 (8)0.0222 (8)0.0044 (7)
C140.0581 (11)0.0758 (12)0.0545 (10)−0.0136 (9)0.0297 (9)−0.0049 (9)
C150.0427 (9)0.0717 (11)0.0528 (10)−0.0017 (8)0.0159 (8)−0.0090 (8)
C160.0449 (8)0.0506 (8)0.0368 (8)−0.0016 (7)0.0101 (7)−0.0024 (6)
C170.0645 (10)0.0375 (8)0.0393 (8)0.0062 (7)0.0123 (7)0.0068 (6)
C180.0516 (9)0.0478 (8)0.0419 (8)0.0150 (7)0.0079 (7)0.0031 (6)
C190.0362 (7)0.0493 (8)0.0352 (7)0.0042 (6)0.0106 (6)−0.0033 (6)
C200.0364 (7)0.0410 (7)0.0293 (7)−0.0022 (6)0.0109 (6)−0.0046 (5)
C210.0367 (8)0.0746 (11)0.0409 (8)0.0023 (7)0.0041 (7)−0.0035 (8)
C220.0477 (9)0.0767 (12)0.0487 (10)−0.0226 (8)0.0118 (8)−0.0122 (8)
C230.0641 (11)0.0534 (9)0.0448 (9)−0.0206 (8)0.0145 (8)−0.0045 (7)
C240.0500 (9)0.0468 (8)0.0351 (8)−0.0079 (7)0.0090 (7)0.0003 (6)
N1—N21.355 (2)C19—C201.399 (2)
N1—C71.464 (2)C19—C211.402 (2)
N1—C91.351 (2)C20—C241.389 (2)
N2—N31.313 (3)C21—C221.375 (3)
N3—C81.340 (3)C22—C231.368 (3)
N4—C101.4634 (17)C23—C241.385 (2)
N4—C111.4293 (19)C1—H10.9300
N4—C201.4351 (18)C3—H30.9300
C1—C21.382 (3)C4—H40.9300
C1—C61.386 (3)C5—H50.9300
C2—C31.387 (2)C6—H60.9300
C2—C71.507 (3)C7—H7A0.9700
C3—C41.373 (3)C7—H7B0.9700
C4—C51.371 (3)C8—H80.9300
C5—C61.373 (4)C10—H10A0.9700
C8—C91.365 (2)C10—H10B0.9700
C9—C101.493 (2)C13—H130.9300
C11—C121.404 (2)C14—H140.9300
C11—C161.390 (2)C15—H150.9300
C12—C131.397 (2)C16—H160.9300
C12—C171.464 (2)C17—H170.9300
C13—C141.372 (3)C18—H180.9300
C14—C151.378 (3)C21—H210.9300
C15—C161.384 (2)C22—H220.9300
C17—C181.330 (3)C23—H230.9300
C18—C191.463 (2)C24—H240.9300
N2—N1—C7119.12 (13)C20—C24—C23120.48 (15)
N2—N1—C9110.26 (13)C2—C1—H1120.00
C7—N1—C9130.61 (14)C6—C1—H1120.00
N1—N2—N3107.76 (15)C2—C3—H3120.00
N2—N3—C8107.75 (16)C4—C3—H3120.00
C10—N4—C11118.25 (12)C3—C4—H4120.00
C10—N4—C20114.87 (11)C5—C4—H4120.00
C11—N4—C20113.50 (11)C4—C5—H5120.00
C2—C1—C6120.31 (18)C6—C5—H5120.00
C1—C2—C3118.80 (17)C1—C6—H6120.00
C1—C2—C7120.80 (15)C5—C6—H6120.00
C3—C2—C7120.31 (16)N1—C7—H7A109.00
C2—C3—C4120.55 (17)N1—C7—H7B109.00
C3—C4—C5120.32 (18)C2—C7—H7A109.00
C4—C5—C6119.96 (19)C2—C7—H7B109.00
C1—C6—C5120.0 (2)H7A—C7—H7B108.00
N1—C7—C2113.40 (14)N3—C8—H8125.00
N3—C8—C9110.56 (17)C9—C8—H8125.00
N1—C9—C8103.67 (14)N4—C10—H10A109.00
N1—C9—C10126.54 (14)N4—C10—H10B109.00
C8—C9—C10129.70 (15)C9—C10—H10A109.00
N4—C10—C9113.52 (12)C9—C10—H10B109.00
N4—C11—C12117.83 (13)H10A—C10—H10B108.00
N4—C11—C16122.52 (12)C12—C13—H13119.00
C12—C11—C16119.64 (14)C14—C13—H13119.00
C11—C12—C13118.32 (15)C13—C14—H14120.00
C11—C12—C17122.57 (14)C15—C14—H14120.00
C13—C12—C17119.11 (14)C14—C15—H15120.00
C12—C13—C14121.53 (16)C16—C15—H15120.00
C13—C14—C15119.85 (18)C11—C16—H16120.00
C14—C15—C16120.07 (17)C15—C16—H16120.00
C11—C16—C15120.59 (15)C12—C17—H17117.00
C12—C17—C18126.86 (14)C18—C17—H17117.00
C17—C18—C19126.24 (16)C17—C18—H18117.00
C18—C19—C20122.19 (14)C19—C18—H18117.00
C18—C19—C21120.05 (14)C19—C21—H21119.00
C20—C19—C21117.73 (14)C22—C21—H21119.00
N4—C20—C19118.53 (12)C21—C22—H22120.00
N4—C20—C24121.38 (12)C23—C22—H22120.00
C19—C20—C24120.08 (14)C22—C23—H23120.00
C19—C21—C22121.63 (16)C24—C23—H23120.00
C21—C22—C23119.93 (17)C20—C24—H24120.00
C22—C23—C24120.09 (17)C23—C24—H24120.00
C7—N1—N2—N3178.33 (15)N3—C8—C9—C10−175.78 (16)
C9—N1—N2—N3−0.1 (2)N1—C9—C10—N448.1 (2)
N2—N1—C7—C2−97.83 (18)C8—C9—C10—N4−136.11 (17)
C9—N1—C7—C280.2 (2)N4—C11—C12—C13177.82 (13)
N2—N1—C9—C8−0.40 (18)N4—C11—C12—C17−2.8 (2)
N2—N1—C9—C10176.29 (15)C16—C11—C12—C13−0.6 (2)
C7—N1—C9—C8−178.59 (17)C16—C11—C12—C17178.82 (14)
C7—N1—C9—C10−1.9 (3)N4—C11—C16—C15−178.14 (14)
N1—N2—N3—C80.6 (2)C12—C11—C16—C150.1 (2)
N2—N3—C8—C9−0.9 (2)C11—C12—C13—C140.6 (2)
C11—N4—C10—C956.44 (17)C17—C12—C13—C14−178.83 (16)
C20—N4—C10—C9−165.14 (13)C11—C12—C17—C18−35.1 (2)
C10—N4—C11—C12−150.96 (13)C13—C12—C17—C18144.31 (17)
C10—N4—C11—C1627.36 (19)C12—C13—C14—C15−0.2 (3)
C20—N4—C11—C1270.09 (15)C13—C14—C15—C16−0.3 (3)
C20—N4—C11—C16−111.60 (15)C14—C15—C16—C110.3 (3)
C10—N4—C20—C19146.64 (13)C12—C17—C18—C19−0.3 (3)
C10—N4—C20—C24−31.99 (19)C17—C18—C19—C2033.4 (2)
C11—N4—C20—C19−72.97 (16)C17—C18—C19—C21−144.41 (17)
C11—N4—C20—C24108.41 (15)C18—C19—C20—N46.5 (2)
C6—C1—C2—C30.8 (2)C18—C19—C20—C24−174.85 (15)
C6—C1—C2—C7−175.74 (16)C21—C19—C20—N4−175.64 (13)
C2—C1—C6—C50.0 (3)C21—C19—C20—C243.0 (2)
C1—C2—C3—C4−1.0 (2)C18—C19—C21—C22175.63 (16)
C7—C2—C3—C4175.58 (15)C20—C19—C21—C22−2.3 (2)
C1—C2—C7—N1−119.86 (17)N4—C20—C24—C23176.75 (15)
C3—C2—C7—N163.67 (18)C19—C20—C24—C23−1.9 (2)
C2—C3—C4—C50.4 (3)C19—C21—C22—C230.3 (3)
C3—C4—C5—C60.4 (3)C21—C22—C23—C240.9 (3)
C4—C5—C6—C1−0.6 (3)C22—C23—C24—C20−0.2 (3)
N3—C8—C9—N10.77 (19)
D—H···AD—HH···AD···AD—H···A
C7—H7A···N40.972.563.173 (2)121
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7—H7A⋯N40.972.563.173 (2)121
  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  5-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-yl]-5H-dibenzo[b,f]azepine.

Authors:  B C Manjunath; K S Vinay Kumar; S Madan Kumar; M P Sadashiva; N K Lokanath
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-13
  1 in total

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