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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1277.
Published online 2010 May 8. doi:  10.1107/S1600536810016004
PMCID: PMC2979523

1-Allyl-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

Abstract

The seven-membered ring in the title compound, C18H16N2O, adopts a boat conformation with the two phenyl­ene carbons representing the stern and the methyl­ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring and the phenyl ring is 62.13 (3)°.

Related literature

For the background information on benzodiazepines, see: Ahabchane et al. (1999 [triangle]).

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Object name is e-66-o1277-scheme1.jpg

Experimental

Crystal data

  • C18H16N2O
  • M r = 276.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1277-efi1.jpg
  • a = 11.4863 (3) Å
  • b = 6.0053 (2) Å
  • c = 20.3667 (5) Å
  • β = 93.525 (1)°
  • V = 1402.21 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.41 × 0.33 × 0.15 mm

Data collection

  • Bruker X8 APEX2 diffractometer
  • 18220 measured reflections
  • 4096 independent reflections
  • 3417 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.153
  • S = 1.07
  • 4096 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016004/bt5257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016004/bt5257Isup2.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

Comment

The compound belongs to the class of benzodiazepine drugs; the background to this class of pharmaceutically potent compounds is explained in an earlier report (Ahabchane et al., 1999). It is readily synthesized by reacting 4-phenyl-1,5-benzodiazepin-2-one with allyl bromide in the presence of a catalyst. The compound features a seven-membered ring fused with a phenylene ring (Scheme I, Fig. 1).

Experimental

To a solution of 4-phenyl-1,5-benzodiazepin-2-one (1 g, 4.2 mmol) in DMF (20 ml) was added allyl bromide (0.5 g, 4.2 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The mixture was stirred at room temperature for 24 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford the title compound as colorless crystals.

Refinement

H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C18H16N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H16N2OF(000) = 584
Mr = 276.33Dx = 1.309 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6537 reflections
a = 11.4863 (3) Åθ = 3.4–32.8°
b = 6.0053 (2) ŵ = 0.08 mm1
c = 20.3667 (5) ÅT = 100 K
β = 93.525 (1)°Block, colorless
V = 1402.21 (7) Å30.41 × 0.33 × 0.15 mm
Z = 4

Data collection

Bruker X8 APEX2 diffractometer3417 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 30.0°, θmin = 2.0°
[var phi] and ω scansh = −16→16
18220 measured reflectionsk = −8→8
4096 independent reflectionsl = −28→28

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0972P)2 + 0.2414P] where P = (Fo2 + 2Fc2)/3
4096 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.32 e Å3

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

xyzUiso*/Ueq
O10.40991 (7)0.27035 (17)0.69505 (4)0.0312 (2)
N10.28667 (7)0.50838 (16)0.63865 (4)0.0198 (2)
N20.45689 (8)0.81559 (16)0.58166 (4)0.0203 (2)
C10.25876 (9)0.64631 (18)0.58323 (5)0.0191 (2)
C20.14324 (9)0.6483 (2)0.55638 (6)0.0235 (2)
H20.08750.55140.57380.028*
C30.10918 (10)0.7889 (2)0.50490 (6)0.0266 (3)
H30.03080.78680.48700.032*
C40.18956 (10)0.9336 (2)0.47934 (6)0.0265 (3)
H40.16641.03060.44410.032*
C50.30340 (10)0.9351 (2)0.50565 (5)0.0235 (2)
H50.35771.03560.48850.028*
C60.34063 (9)0.79147 (18)0.55714 (5)0.0194 (2)
C70.51760 (9)0.64251 (18)0.59890 (5)0.0186 (2)
C80.46876 (9)0.40922 (18)0.59144 (5)0.0207 (2)
H8A0.53210.29740.59570.025*
H8B0.42620.39070.54800.025*
C90.38662 (9)0.38380 (19)0.64646 (5)0.0208 (2)
C100.63667 (9)0.67685 (19)0.62955 (5)0.0202 (2)
C110.66216 (10)0.8679 (2)0.66689 (6)0.0236 (2)
H110.60310.97560.67270.028*
C120.77389 (10)0.9006 (2)0.69558 (6)0.0289 (3)
H120.79071.03020.72120.035*
C130.86102 (10)0.7447 (3)0.68696 (6)0.0311 (3)
H130.93700.76680.70700.037*
C140.83690 (10)0.5572 (2)0.64908 (7)0.0323 (3)
H140.89690.45240.64230.039*
C150.72483 (10)0.5216 (2)0.62083 (6)0.0278 (3)
H150.70840.39120.59550.033*
C160.20572 (10)0.5022 (2)0.69194 (5)0.0252 (2)
H16A0.16030.64240.69070.030*
H16B0.25220.49790.73450.030*
C170.12199 (10)0.3107 (2)0.68985 (6)0.0289 (3)
H170.06870.30460.72360.035*
C180.11499 (11)0.1503 (2)0.64588 (7)0.0343 (3)
H18A0.16640.14880.61110.041*
H18B0.05850.03570.64890.041*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0268 (4)0.0368 (5)0.0297 (4)0.0035 (4)0.0000 (3)0.0133 (4)
N10.0167 (4)0.0233 (5)0.0195 (4)0.0001 (3)0.0013 (3)0.0025 (3)
N20.0174 (4)0.0204 (5)0.0228 (4)−0.0012 (3)−0.0004 (3)0.0008 (3)
C10.0182 (4)0.0190 (5)0.0199 (5)0.0011 (4)−0.0008 (4)−0.0002 (4)
C20.0184 (5)0.0245 (6)0.0272 (5)−0.0004 (4)−0.0013 (4)0.0006 (4)
C30.0217 (5)0.0290 (6)0.0282 (6)0.0039 (4)−0.0060 (4)−0.0007 (5)
C40.0282 (5)0.0277 (6)0.0230 (5)0.0065 (4)−0.0026 (4)0.0034 (4)
C50.0254 (5)0.0213 (5)0.0239 (5)0.0013 (4)0.0010 (4)0.0029 (4)
C60.0184 (4)0.0189 (5)0.0208 (5)0.0013 (4)−0.0007 (4)−0.0007 (4)
C70.0175 (4)0.0196 (5)0.0188 (4)−0.0006 (4)0.0028 (3)−0.0006 (4)
C80.0194 (5)0.0184 (5)0.0244 (5)0.0001 (4)0.0024 (4)−0.0006 (4)
C90.0183 (5)0.0203 (5)0.0235 (5)−0.0022 (4)−0.0011 (4)0.0019 (4)
C100.0175 (4)0.0231 (5)0.0200 (5)0.0003 (4)0.0011 (4)0.0015 (4)
C110.0225 (5)0.0236 (6)0.0245 (5)−0.0011 (4)0.0002 (4)−0.0002 (4)
C120.0269 (6)0.0338 (7)0.0254 (5)−0.0077 (5)−0.0030 (4)−0.0013 (5)
C130.0187 (5)0.0456 (8)0.0286 (6)−0.0047 (5)−0.0028 (4)0.0060 (5)
C140.0184 (5)0.0401 (7)0.0383 (7)0.0056 (5)0.0009 (4)0.0014 (6)
C150.0208 (5)0.0300 (6)0.0326 (6)0.0041 (4)0.0010 (4)−0.0045 (5)
C160.0242 (5)0.0317 (6)0.0202 (5)0.0013 (4)0.0045 (4)−0.0019 (4)
C170.0203 (5)0.0373 (7)0.0294 (6)0.0004 (5)0.0044 (4)0.0088 (5)
C180.0283 (6)0.0298 (7)0.0447 (7)−0.0052 (5)0.0009 (5)0.0063 (6)

Geometric parameters (Å, °)

O1—C91.2176 (14)C8—H8B0.9900
N1—C91.3713 (14)C10—C151.3956 (15)
N1—C11.4207 (14)C10—C111.3975 (16)
N1—C161.4725 (13)C11—C121.3910 (15)
N2—C71.2884 (14)C11—H110.9500
N2—C61.4041 (13)C12—C131.3898 (19)
C1—C21.4038 (14)C12—H120.9500
C1—C61.4100 (15)C13—C141.383 (2)
C2—C31.3841 (16)C13—H130.9500
C2—H20.9500C14—C151.3938 (16)
C3—C41.3918 (18)C14—H140.9500
C3—H30.9500C15—H150.9500
C4—C51.3823 (16)C16—C171.4981 (18)
C4—H40.9500C16—H16A0.9900
C5—C61.4040 (15)C16—H16B0.9900
C5—H50.9500C17—C181.314 (2)
C7—C101.4824 (14)C17—H170.9500
C7—C81.5133 (15)C18—H18A0.9500
C8—C91.5164 (15)C18—H18B0.9500
C8—H8A0.9900
C9—N1—C1123.83 (9)O1—C9—C8122.78 (10)
C9—N1—C16117.57 (9)N1—C9—C8114.45 (9)
C1—N1—C16118.58 (9)C15—C10—C11119.22 (10)
C7—N2—C6120.05 (10)C15—C10—C7120.75 (10)
C2—C1—C6118.97 (10)C11—C10—C7120.02 (10)
C2—C1—N1118.43 (9)C12—C11—C10120.11 (11)
C6—C1—N1122.46 (9)C12—C11—H11119.9
C3—C2—C1121.10 (11)C10—C11—H11119.9
C3—C2—H2119.4C13—C12—C11120.31 (12)
C1—C2—H2119.4C13—C12—H12119.8
C2—C3—C4120.08 (10)C11—C12—H12119.8
C2—C3—H3120.0C14—C13—C12119.86 (11)
C4—C3—H3120.0C14—C13—H13120.1
C5—C4—C3119.50 (11)C12—C13—H13120.1
C5—C4—H4120.2C13—C14—C15120.22 (12)
C3—C4—H4120.2C13—C14—H14119.9
C4—C5—C6121.54 (11)C15—C14—H14119.9
C4—C5—H5119.2C14—C15—C10120.26 (12)
C6—C5—H5119.2C14—C15—H15119.9
N2—C6—C5116.21 (10)C10—C15—H15119.9
N2—C6—C1124.85 (9)N1—C16—C17115.57 (10)
C5—C6—C1118.79 (10)N1—C16—H16A108.4
N2—C7—C10118.19 (10)C17—C16—H16A108.4
N2—C7—C8121.90 (9)N1—C16—H16B108.4
C10—C7—C8119.86 (9)C17—C16—H16B108.4
C7—C8—C9105.22 (9)H16A—C16—H16B107.4
C7—C8—H8A110.7C18—C17—C16126.47 (11)
C9—C8—H8A110.7C18—C17—H17116.8
C7—C8—H8B110.7C16—C17—H17116.8
C9—C8—H8B110.7C17—C18—H18A120.0
H8A—C8—H8B108.8C17—C18—H18B120.0
O1—C9—N1122.69 (10)H18A—C18—H18B120.0
C9—N1—C1—C2138.75 (11)C1—N1—C9—O1178.41 (11)
C16—N1—C1—C2−42.98 (14)C16—N1—C9—O10.11 (17)
C9—N1—C1—C6−45.56 (16)C1—N1—C9—C81.68 (15)
C16—N1—C1—C6132.71 (11)C16—N1—C9—C8−176.62 (9)
C6—C1—C2—C30.28 (17)C7—C8—C9—O1−106.66 (12)
N1—C1—C2—C3176.12 (11)C7—C8—C9—N170.06 (12)
C1—C2—C3—C4−0.74 (18)N2—C7—C10—C15−148.72 (11)
C2—C3—C4—C50.15 (18)C8—C7—C10—C1533.95 (15)
C3—C4—C5—C60.91 (18)N2—C7—C10—C1130.35 (15)
C7—N2—C6—C5−142.10 (11)C8—C7—C10—C11−146.97 (11)
C7—N2—C6—C142.31 (15)C15—C10—C11—C12−0.79 (17)
C4—C5—C6—N2−177.22 (10)C7—C10—C11—C12−179.88 (10)
C4—C5—C6—C1−1.36 (17)C10—C11—C12—C130.45 (18)
C2—C1—C6—N2176.23 (10)C11—C12—C13—C140.70 (19)
N1—C1—C6—N20.56 (17)C12—C13—C14—C15−1.5 (2)
C2—C1—C6—C50.75 (16)C13—C14—C15—C101.2 (2)
N1—C1—C6—C5−174.92 (10)C11—C10—C15—C14−0.01 (18)
C6—N2—C7—C10−175.11 (9)C7—C10—C15—C14179.07 (11)
C6—N2—C7—C82.15 (15)C9—N1—C16—C17−83.98 (13)
N2—C7—C8—C9−75.36 (12)C1—N1—C16—C1797.64 (12)
C10—C7—C8—C9101.86 (10)N1—C16—C17—C180.49 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5257).

References

  • Ahabchane, A. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519–523.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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