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

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ISSN: 2056-9890

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

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, 0000 Rabat, Morocco, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 29 April 2010; accepted 30 April 2010; online 8 May 2010)

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[Ahabchane, A. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519-523.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N2O

  • Mr = 276.33

  • Monoclinic, P 21 /n

  • 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)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C18H16N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-Allyl-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one top
Crystal data top
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 top
Bruker X8 APEX2
diffractometer
3417 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 30.0°, θmin = 2.0°
ϕ and ω scansh = 1616
18220 measured reflectionsk = 88
4096 independent reflectionsl = 2828
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.07 w = 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 = 0.33 e Å3
Crystal data top
C18H16N2OV = 1402.21 (7) Å3
Mr = 276.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.4863 (3) ŵ = 0.08 mm1
b = 6.0053 (2) ÅT = 100 K
c = 20.3667 (5) Å0.41 × 0.33 × 0.15 mm
β = 93.525 (1)°
Data collection top
Bruker X8 APEX2
diffractometer
3417 reflections with I > 2σ(I)
18220 measured reflectionsRint = 0.030
4096 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.07Δρmax = 0.41 e Å3
4096 reflectionsΔρmin = 0.33 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C242.98 (14)C16—N1—C9—O10.11 (17)
C9—N1—C1—C645.56 (16)C1—N1—C9—C81.68 (15)
C16—N1—C1—C6132.71 (11)C16—N1—C9—C8176.62 (9)
C6—C1—C2—C30.28 (17)C7—C8—C9—O1106.66 (12)
N1—C1—C2—C3176.12 (11)C7—C8—C9—N170.06 (12)
C1—C2—C3—C40.74 (18)N2—C7—C10—C15148.72 (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—C5142.10 (11)C8—C7—C10—C11146.97 (11)
C7—N2—C6—C142.31 (15)C15—C10—C11—C120.79 (17)
C4—C5—C6—N2177.22 (10)C7—C10—C11—C12179.88 (10)
C4—C5—C6—C11.36 (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—C151.5 (2)
C2—C1—C6—C50.75 (16)C13—C14—C15—C101.2 (2)
N1—C1—C6—C5174.92 (10)C11—C10—C15—C140.01 (18)
C6—N2—C7—C10175.11 (9)C7—C10—C15—C14179.07 (11)
C6—N2—C7—C82.15 (15)C9—N1—C16—C1783.98 (13)
N2—C7—C8—C975.36 (12)C1—N1—C16—C1797.64 (12)
C10—C7—C8—C9101.86 (10)N1—C16—C17—C180.49 (18)

Experimental details

Crystal data
Chemical formulaC18H16N2O
Mr276.33
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)11.4863 (3), 6.0053 (2), 20.3667 (5)
β (°) 93.525 (1)
V3)1402.21 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.41 × 0.33 × 0.15
Data collection
DiffractometerBruker X8 APEX2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18220, 4096, 3417
Rint0.030
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.153, 1.07
No. of reflections4096
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.33

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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

References

First citationAhabchane, A. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519–523.  CAS
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.

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