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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3150.
Published online 2009 November 21. doi:  10.1107/S160053680904851X
PMCID: PMC2972173

3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione

Abstract

The title compound, C26H24N2O2, features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the allyl­dimethyl­amino­methyl-bearing C atom as the prow and the fused-ring C atoms as the stern).

Related literature

For the crystal structure of benzo­diazepin-2,4-dione, see: Négrier et al. (2006 [triangle]).

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Object name is e-65-o3150-scheme1.jpg

Experimental

Crystal data

  • C26H24N2O2
  • M r = 396.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3150-efi1.jpg
  • a = 9.2603 (4) Å
  • b = 14.0037 (6) Å
  • c = 16.2249 (7) Å
  • β = 91.996 (1)°
  • V = 2102.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 193 K
  • 0.40 × 0.40 × 0.07 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: none
  • 27620 measured reflections
  • 4820 independent reflections
  • 2934 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.117
  • S = 1.00
  • 4820 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904851X/sj2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904851X/sj2680Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution of the potassium t-butoxide (0.24 g, 2.13 mmol) in THF (15 ml) was added 1,5-dibenzyl-1,5-benzodiazepine-2,4-dione (0.50 g, 1.40 mmol) and allyl bromide (0.20 ml, 1.88 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer chromatography. The mixture was filtered and the solution evaporated to give colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C26H24N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C26H24N2O2F(000) = 840
Mr = 396.47Dx = 1.252 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4269 reflections
a = 9.2603 (4) Åθ = 2.5–25.0°
b = 14.0037 (6) ŵ = 0.08 mm1
c = 16.2249 (7) ÅT = 193 K
β = 91.996 (1)°Plate, colorless
V = 2102.7 (2) Å30.40 × 0.40 × 0.07 mm
Z = 4

Data collection

Bruker APEXII diffractometer2934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
graphiteθmax = 27.5°, θmin = 1.9°
[var phi] and ω scansh = −11→12
27620 measured reflectionsk = −18→18
4820 independent reflectionsl = −21→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0487P)2 + 0.414P] where P = (Fo2 + 2Fc2)/3
4820 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.17 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.49018 (14)0.26136 (9)0.33899 (7)0.0470 (3)
O20.33507 (16)0.40157 (8)0.16934 (7)0.0498 (4)
N10.50477 (15)0.15481 (9)0.23332 (8)0.0330 (3)
N20.37563 (15)0.26484 (9)0.09974 (7)0.0320 (3)
C10.43555 (19)0.22301 (11)0.27747 (10)0.0348 (4)
C20.33193 (19)0.31439 (11)0.16711 (9)0.0350 (4)
C30.28998 (18)0.25375 (11)0.24091 (9)0.0336 (4)
H30.23490.19630.22100.040*
C40.2006 (2)0.30886 (12)0.30184 (10)0.0409 (4)
H4A0.19790.27250.35410.049*
H4B0.24790.37090.31390.049*
C50.0492 (2)0.32639 (13)0.27024 (11)0.0485 (5)
H50.03650.34190.21350.058*
C6−0.0667 (3)0.32235 (16)0.31310 (14)0.0658 (6)
H6A−0.05950.30710.37010.079*
H6B−0.15850.33470.28740.079*
C70.43855 (17)0.10939 (11)0.16252 (9)0.0294 (3)
C80.37894 (16)0.16300 (10)0.09694 (9)0.0285 (3)
C90.32362 (17)0.11561 (12)0.02736 (9)0.0332 (4)
H90.28520.1515−0.01800.040*
C100.32381 (18)0.01744 (12)0.02331 (10)0.0371 (4)
H100.2853−0.0140−0.02450.045*
C110.38017 (18)−0.03554 (12)0.08892 (10)0.0361 (4)
H110.3788−0.10330.08660.043*
C120.43813 (17)0.01011 (11)0.15748 (10)0.0331 (4)
H120.4784−0.02650.20190.040*
C130.65246 (19)0.12564 (13)0.25940 (10)0.0407 (4)
H13A0.65120.05800.27720.049*
H13B0.68530.16480.30730.049*
C140.75779 (18)0.13696 (12)0.19117 (10)0.0382 (4)
C150.7462 (2)0.21035 (14)0.13427 (12)0.0483 (5)
H150.66990.25540.13760.058*
C160.8450 (2)0.21874 (16)0.07231 (13)0.0603 (6)
H160.83530.26890.03310.072*
C170.9570 (2)0.15453 (16)0.06759 (14)0.0606 (6)
H171.02430.16020.02500.073*
C180.9714 (2)0.08237 (15)0.12436 (14)0.0564 (5)
H181.04980.03890.12180.068*
C190.8714 (2)0.07300 (13)0.18536 (12)0.0459 (5)
H190.88080.02200.22380.055*
C200.4289 (2)0.32016 (12)0.02996 (10)0.0380 (4)
H20A0.47800.2757−0.00730.046*
H20B0.50230.36590.05160.046*
C210.3168 (2)0.37497 (12)−0.02019 (9)0.0385 (4)
C220.3657 (3)0.43780 (13)−0.07970 (11)0.0553 (5)
H220.46640.4466−0.08580.066*
C230.2682 (4)0.48731 (17)−0.12977 (13)0.0764 (8)
H230.30210.5301−0.17020.092*
C240.1224 (4)0.47491 (18)−0.12138 (15)0.0839 (9)
H240.05580.5084−0.15660.101*
C250.0723 (3)0.41385 (16)−0.06193 (15)0.0704 (7)
H25−0.02860.4058−0.05570.084*
C260.1706 (2)0.36411 (13)−0.01120 (11)0.0487 (5)
H260.13630.32240.02990.058*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0684 (9)0.0398 (7)0.0320 (6)−0.0053 (6)−0.0109 (6)−0.0058 (5)
O20.0876 (10)0.0251 (7)0.0365 (7)−0.0007 (6)0.0008 (7)−0.0003 (5)
N10.0420 (8)0.0286 (7)0.0280 (7)−0.0001 (6)−0.0064 (6)0.0014 (6)
N20.0451 (8)0.0256 (7)0.0254 (7)0.0015 (6)0.0000 (6)0.0024 (5)
C10.0534 (11)0.0253 (8)0.0255 (8)−0.0046 (8)−0.0026 (7)0.0035 (7)
C20.0494 (11)0.0275 (9)0.0277 (8)0.0007 (8)−0.0044 (7)0.0003 (7)
C30.0496 (10)0.0258 (8)0.0251 (8)0.0005 (7)−0.0003 (7)−0.0025 (6)
C40.0616 (12)0.0328 (9)0.0283 (9)0.0048 (9)0.0038 (8)−0.0028 (7)
C50.0664 (14)0.0411 (11)0.0381 (10)0.0129 (10)0.0013 (9)−0.0056 (8)
C60.0641 (15)0.0742 (16)0.0593 (13)−0.0053 (12)0.0039 (11)−0.0084 (12)
C70.0322 (9)0.0282 (8)0.0277 (8)−0.0006 (7)0.0018 (7)−0.0014 (6)
C80.0338 (9)0.0250 (8)0.0268 (8)0.0005 (7)0.0042 (7)−0.0010 (6)
C90.0353 (9)0.0374 (10)0.0267 (8)0.0040 (7)−0.0012 (7)−0.0031 (7)
C100.0361 (10)0.0390 (10)0.0363 (9)−0.0002 (8)0.0008 (7)−0.0131 (8)
C110.0394 (10)0.0270 (8)0.0425 (10)0.0000 (7)0.0090 (8)−0.0064 (7)
C120.0365 (9)0.0287 (9)0.0343 (9)0.0029 (7)0.0040 (7)0.0029 (7)
C130.0466 (11)0.0368 (10)0.0379 (9)0.0003 (8)−0.0112 (8)0.0053 (8)
C140.0378 (10)0.0328 (9)0.0430 (10)−0.0051 (8)−0.0135 (8)0.0008 (8)
C150.0398 (11)0.0435 (11)0.0613 (12)−0.0011 (9)−0.0048 (9)0.0144 (9)
C160.0472 (12)0.0683 (15)0.0654 (14)−0.0086 (11)0.0005 (10)0.0253 (11)
C170.0401 (12)0.0711 (15)0.0707 (14)−0.0050 (11)0.0047 (10)0.0036 (12)
C180.0400 (11)0.0509 (13)0.0779 (15)0.0021 (9)−0.0041 (11)−0.0037 (11)
C190.0426 (11)0.0368 (10)0.0572 (12)−0.0012 (9)−0.0127 (9)0.0023 (9)
C200.0502 (11)0.0339 (9)0.0302 (8)−0.0051 (8)0.0038 (8)0.0057 (7)
C210.0631 (13)0.0280 (9)0.0243 (8)0.0036 (8)−0.0005 (8)−0.0006 (7)
C220.0937 (16)0.0383 (11)0.0345 (10)0.0081 (11)0.0103 (10)0.0069 (8)
C230.141 (3)0.0484 (14)0.0396 (12)0.0187 (16)0.0015 (14)0.0142 (10)
C240.132 (3)0.0580 (16)0.0587 (15)0.0313 (17)−0.0366 (17)0.0071 (12)
C250.0779 (16)0.0554 (14)0.0756 (16)0.0177 (12)−0.0285 (13)−0.0023 (12)
C260.0633 (14)0.0394 (11)0.0425 (10)0.0056 (10)−0.0105 (9)0.0016 (8)

Geometric parameters (Å, °)

O1—C11.2271 (19)C13—C141.509 (2)
O2—C21.2216 (19)C13—H13A0.9900
N1—C11.367 (2)C13—H13B0.9900
N1—C71.4321 (19)C14—C151.383 (2)
N1—C131.475 (2)C14—C191.388 (2)
N2—C21.3678 (19)C15—C161.388 (3)
N2—C81.4273 (19)C15—H150.9500
N2—C201.4710 (19)C16—C171.377 (3)
C1—C31.516 (2)C16—H160.9500
C2—C31.529 (2)C17—C181.371 (3)
C3—C41.521 (2)C17—H170.9500
C3—H31.0000C18—C191.385 (3)
C4—C51.496 (3)C18—H180.9500
C4—H4A0.9900C19—H190.9500
C4—H4B0.9900C20—C211.506 (2)
C5—C61.300 (3)C20—H20A0.9900
C5—H50.9500C20—H20B0.9900
C6—H6A0.9500C21—C261.376 (3)
C6—H6B0.9500C21—C221.393 (2)
C7—C121.393 (2)C22—C231.380 (3)
C7—C81.400 (2)C22—H220.9500
C8—C91.392 (2)C23—C241.372 (4)
C9—C101.376 (2)C23—H230.9500
C9—H90.9500C24—C251.381 (4)
C10—C111.385 (2)C24—H240.9500
C10—H100.9500C25—C261.392 (3)
C11—C121.376 (2)C25—H250.9500
C11—H110.9500C26—H260.9500
C12—H120.9500
C1—N1—C7122.36 (14)N1—C13—C14112.15 (13)
C1—N1—C13119.35 (13)N1—C13—H13A109.2
C7—N1—C13118.29 (13)C14—C13—H13A109.2
C2—N2—C8122.66 (13)N1—C13—H13B109.2
C2—N2—C20117.67 (13)C14—C13—H13B109.2
C8—N2—C20119.58 (12)H13A—C13—H13B107.9
O1—C1—N1123.00 (16)C15—C14—C19118.41 (17)
O1—C1—C3121.99 (15)C15—C14—C13122.04 (16)
N1—C1—C3114.85 (13)C19—C14—C13119.55 (16)
O2—C2—N2121.55 (15)C14—C15—C16120.56 (18)
O2—C2—C3122.56 (14)C14—C15—H15119.7
N2—C2—C3115.74 (13)C16—C15—H15119.7
C1—C3—C4112.72 (13)C17—C16—C15120.13 (19)
C1—C3—C2102.56 (13)C17—C16—H16119.9
C4—C3—C2112.70 (13)C15—C16—H16119.9
C1—C3—H3109.5C18—C17—C16120.0 (2)
C4—C3—H3109.5C18—C17—H17120.0
C2—C3—H3109.5C16—C17—H17120.0
C5—C4—C3112.65 (14)C17—C18—C19119.90 (19)
C5—C4—H4A109.1C17—C18—H18120.1
C3—C4—H4A109.1C19—C18—H18120.1
C5—C4—H4B109.1C18—C19—C14120.98 (18)
C3—C4—H4B109.1C18—C19—H19119.5
H4A—C4—H4B107.8C14—C19—H19119.5
C6—C5—C4126.20 (19)N2—C20—C21116.17 (14)
C6—C5—H5116.9N2—C20—H20A108.2
C4—C5—H5116.9C21—C20—H20A108.2
C5—C6—H6A120.0N2—C20—H20B108.2
C5—C6—H6B120.0C21—C20—H20B108.2
H6A—C6—H6B120.0H20A—C20—H20B107.4
C12—C7—C8119.37 (14)C26—C21—C22119.19 (18)
C12—C7—N1119.39 (14)C26—C21—C20123.27 (15)
C8—C7—N1121.20 (14)C22—C21—C20117.52 (18)
C9—C8—C7119.02 (14)C23—C22—C21120.2 (2)
C9—C8—N2119.64 (14)C23—C22—H22119.9
C7—C8—N2121.34 (13)C21—C22—H22119.9
C10—C9—C8120.93 (15)C24—C23—C22120.2 (2)
C10—C9—H9119.5C24—C23—H23119.9
C8—C9—H9119.5C22—C23—H23119.9
C9—C10—C11119.97 (15)C23—C24—C25120.2 (2)
C9—C10—H10120.0C23—C24—H24119.9
C11—C10—H10120.0C25—C24—H24119.9
C12—C11—C10119.91 (15)C24—C25—C26119.6 (3)
C12—C11—H11120.0C24—C25—H25120.2
C10—C11—H11120.0C26—C25—H25120.2
C11—C12—C7120.77 (15)C21—C26—C25120.5 (2)
C11—C12—H12119.6C21—C26—H26119.8
C7—C12—H12119.6C25—C26—H26119.8
C7—N1—C1—O1178.80 (15)C7—C8—C9—C101.6 (2)
C13—N1—C1—O1−0.6 (2)N2—C8—C9—C10−179.23 (15)
C7—N1—C1—C3−5.8 (2)C8—C9—C10—C11−0.3 (2)
C13—N1—C1—C3174.81 (13)C9—C10—C11—C12−1.1 (2)
C8—N2—C2—O2177.22 (16)C10—C11—C12—C71.2 (2)
C20—N2—C2—O20.8 (2)C8—C7—C12—C110.1 (2)
C8—N2—C2—C31.5 (2)N1—C7—C12—C11−177.57 (14)
C20—N2—C2—C3−174.87 (14)C1—N1—C13—C14−124.15 (16)
O1—C1—C3—C4−19.6 (2)C7—N1—C13—C1456.45 (19)
N1—C1—C3—C4164.96 (14)N1—C13—C14—C1534.5 (2)
O1—C1—C3—C2101.85 (17)N1—C13—C14—C19−146.39 (15)
N1—C1—C3—C2−73.59 (16)C19—C14—C15—C160.8 (3)
O2—C2—C3—C1−99.46 (19)C13—C14—C15—C16179.95 (18)
N2—C2—C3—C176.21 (17)C14—C15—C16—C17−0.8 (3)
O2—C2—C3—C422.0 (2)C15—C16—C17—C18−0.3 (3)
N2—C2—C3—C4−162.32 (14)C16—C17—C18—C191.4 (3)
C1—C3—C4—C5−171.39 (14)C17—C18—C19—C14−1.3 (3)
C2—C3—C4—C573.10 (19)C15—C14—C19—C180.2 (3)
C3—C4—C5—C6140.7 (2)C13—C14—C19—C18−178.88 (17)
C1—N1—C7—C12−129.21 (16)C2—N2—C20—C21−71.74 (19)
C13—N1—C7—C1250.2 (2)C8—N2—C20—C21111.77 (17)
C1—N1—C7—C853.2 (2)N2—C20—C21—C26−9.8 (2)
C13—N1—C7—C8−127.46 (16)N2—C20—C21—C22171.75 (15)
C12—C7—C8—C9−1.5 (2)C26—C21—C22—C23−1.0 (3)
N1—C7—C8—C9176.16 (14)C20—C21—C22—C23177.51 (17)
C12—C7—C8—N2179.35 (14)C21—C22—C23—C24−0.1 (3)
N1—C7—C8—N2−3.0 (2)C22—C23—C24—C251.0 (4)
C2—N2—C8—C9134.46 (16)C23—C24—C25—C26−0.8 (4)
C20—N2—C8—C9−49.2 (2)C22—C21—C26—C251.2 (3)
C2—N2—C8—C7−46.4 (2)C20—C21—C26—C25−177.19 (17)
C20—N2—C8—C7129.94 (16)C24—C25—C26—C21−0.4 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2680).

References

  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Négrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, 175.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

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