organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bService Commun Rayons-X FR2599, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, B.P. 1014 Avenue Ibn Batout, Rabat, Morocco, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 12 November 2009; accepted 15 November 2009; online 21 November 2009)

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[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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N2O2

  • Mr = 396.47

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C26H24N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione top
Crystal data top
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 top
Bruker APEXII
diffractometer
2934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = 1112
27620 measured reflectionsk = 1818
4820 independent reflectionsl = 2116
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.00 w = 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 = 0.18 e Å3
Crystal data top
C26H24N2O2V = 2102.7 (2) Å3
Mr = 396.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2603 (4) ŵ = 0.08 mm1
b = 14.0037 (6) ÅT = 193 K
c = 16.2249 (7) Å0.40 × 0.40 × 0.07 mm
β = 91.996 (1)°
Data collection top
Bruker APEXII
diffractometer
2934 reflections with I > 2σ(I)
27620 measured reflectionsRint = 0.050
4820 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
4820 reflectionsΔρmin = 0.18 e Å3
271 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
C60.0667 (3)0.32235 (16)0.31310 (14)0.0658 (6)
H6A0.05950.30710.37010.079*
H6B0.15850.33470.28740.079*
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)
H90.28520.15150.01800.040*
C100.32381 (18)0.01744 (12)0.02331 (10)0.0371 (4)
H100.28530.01400.02450.045*
C110.38017 (18)0.03554 (12)0.08892 (10)0.0361 (4)
H110.37880.10330.08660.043*
C120.43813 (17)0.01011 (11)0.15748 (10)0.0331 (4)
H120.47840.02650.20190.040*
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)
H20A0.47800.27570.00730.046*
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)
H220.46640.44660.08580.066*
C230.2682 (4)0.48731 (17)0.12977 (13)0.0764 (8)
H230.30210.53010.17020.092*
C240.1224 (4)0.47491 (18)0.12138 (15)0.0839 (9)
H240.05580.50840.15660.101*
C250.0723 (3)0.41385 (16)0.06193 (15)0.0704 (7)
H250.02860.40580.05570.084*
C260.1706 (2)0.36411 (13)0.01120 (11)0.0487 (5)
H260.13630.32240.02990.058*
Atomic displacement parameters (Å2) top
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, º) top
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—O10.6 (2)N2—C8—C9—C10179.23 (15)
C7—N1—C1—C35.8 (2)C8—C9—C10—C110.3 (2)
C13—N1—C1—C3174.81 (13)C9—C10—C11—C121.1 (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—C11177.57 (14)
C20—N2—C2—C3174.87 (14)C1—N1—C13—C14124.15 (16)
O1—C1—C3—C419.6 (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—C19146.39 (15)
N1—C1—C3—C273.59 (16)C19—C14—C15—C160.8 (3)
O2—C2—C3—C199.46 (19)C13—C14—C15—C16179.95 (18)
N2—C2—C3—C176.21 (17)C14—C15—C16—C170.8 (3)
O2—C2—C3—C422.0 (2)C15—C16—C17—C180.3 (3)
N2—C2—C3—C4162.32 (14)C16—C17—C18—C191.4 (3)
C1—C3—C4—C5171.39 (14)C17—C18—C19—C141.3 (3)
C2—C3—C4—C573.10 (19)C15—C14—C19—C180.2 (3)
C3—C4—C5—C6140.7 (2)C13—C14—C19—C18178.88 (17)
C1—N1—C7—C12129.21 (16)C2—N2—C20—C2171.74 (19)
C13—N1—C7—C1250.2 (2)C8—N2—C20—C21111.77 (17)
C1—N1—C7—C853.2 (2)N2—C20—C21—C269.8 (2)
C13—N1—C7—C8127.46 (16)N2—C20—C21—C22171.75 (15)
C12—C7—C8—C91.5 (2)C26—C21—C22—C231.0 (3)
N1—C7—C8—C9176.16 (14)C20—C21—C22—C23177.51 (17)
C12—C7—C8—N2179.35 (14)C21—C22—C23—C240.1 (3)
N1—C7—C8—N23.0 (2)C22—C23—C24—C251.0 (4)
C2—N2—C8—C9134.46 (16)C23—C24—C25—C260.8 (4)
C20—N2—C8—C949.2 (2)C22—C21—C26—C251.2 (3)
C2—N2—C8—C746.4 (2)C20—C21—C26—C25177.19 (17)
C20—N2—C8—C7129.94 (16)C24—C25—C26—C210.4 (3)

Experimental details

Crystal data
Chemical formulaC26H24N2O2
Mr396.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)9.2603 (4), 14.0037 (6), 16.2249 (7)
β (°) 91.996 (1)
V3)2102.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.40 × 0.07
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
27620, 4820, 2934
Rint0.050
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.117, 1.00
No. of reflections4820
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNégrier, 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.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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