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

Ballo, D.; Ahabchane, N.H.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810016004

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1277

https://doi.org/10.1107/S1600536810016004

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

Daouda Ballo,^a Noureddine Hamou Ahabchane,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^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 ).

Experimental

Crystal data

C₁₈H₁₆N₂O
M_r = 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)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.153
S = 1.07
4096 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016004/bt5257Isup2.hkl

checkCIF report

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.

Structure description top

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

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

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

C₁₈H₁₆N₂O	F(000) = 584
M_r = 276.33	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6537 reflections
a = 11.4863 (3) Å	θ = 3.4–32.8°
b = 6.0053 (2) Å	µ = 0.08 mm⁻¹
c = 20.3667 (5) Å	T = 100 K
β = 93.525 (1)°	Block, colorless
V = 1402.21 (7) Å³	0.41 × 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 tube	R_int = 0.030
Graphite monochromator	θ_max = 30.0°, θ_min = 2.0°
φ and ω scans	h = −16→16
18220 measured reflections	k = −8→8
4096 independent reflections	l = −28→28

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0972P)² + 0.2414P] where P = (F_o² + 2F_c²)/3
4096 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O	V = 1402.21 (7) Å³
M_r = 276.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4863 (3) Å	µ = 0.08 mm⁻¹
b = 6.0053 (2) Å	T = 100 K
c = 20.3667 (5) Å	0.41 × 0.33 × 0.15 mm
β = 93.525 (1)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.07	Δρ_max = 0.41 e Å⁻³
4096 reflections	Δρ_min = −0.33 e Å⁻³
190 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.40991 (7)	0.27035 (17)	0.69505 (4)	0.0312 (2)
N1	0.28667 (7)	0.50838 (16)	0.63865 (4)	0.0198 (2)
N2	0.45689 (8)	0.81559 (16)	0.58166 (4)	0.0203 (2)
C1	0.25876 (9)	0.64631 (18)	0.58323 (5)	0.0191 (2)
C2	0.14324 (9)	0.6483 (2)	0.55638 (6)	0.0235 (2)
H2	0.0875	0.5514	0.5738	0.028*
C3	0.10918 (10)	0.7889 (2)	0.50490 (6)	0.0266 (3)
H3	0.0308	0.7868	0.4870	0.032*
C4	0.18956 (10)	0.9336 (2)	0.47934 (6)	0.0265 (3)
H4	0.1664	1.0306	0.4441	0.032*
C5	0.30340 (10)	0.9351 (2)	0.50565 (5)	0.0235 (2)
H5	0.3577	1.0356	0.4885	0.028*
C6	0.34063 (9)	0.79147 (18)	0.55714 (5)	0.0194 (2)
C7	0.51760 (9)	0.64251 (18)	0.59890 (5)	0.0186 (2)
C8	0.46876 (9)	0.40922 (18)	0.59144 (5)	0.0207 (2)
H8A	0.5321	0.2974	0.5957	0.025*
H8B	0.4262	0.3907	0.5480	0.025*
C9	0.38662 (9)	0.38380 (19)	0.64646 (5)	0.0208 (2)
C10	0.63667 (9)	0.67685 (19)	0.62955 (5)	0.0202 (2)
C11	0.66216 (10)	0.8679 (2)	0.66689 (6)	0.0236 (2)
H11	0.6031	0.9756	0.6727	0.028*
C12	0.77389 (10)	0.9006 (2)	0.69558 (6)	0.0289 (3)
H12	0.7907	1.0302	0.7212	0.035*
C13	0.86102 (10)	0.7447 (3)	0.68696 (6)	0.0311 (3)
H13	0.9370	0.7668	0.7070	0.037*
C14	0.83690 (10)	0.5572 (2)	0.64908 (7)	0.0323 (3)
H14	0.8969	0.4524	0.6423	0.039*
C15	0.72483 (10)	0.5216 (2)	0.62083 (6)	0.0278 (3)
H15	0.7084	0.3912	0.5955	0.033*
C16	0.20572 (10)	0.5022 (2)	0.69194 (5)	0.0252 (2)
H16A	0.1603	0.6424	0.6907	0.030*
H16B	0.2522	0.4979	0.7345	0.030*
C17	0.12199 (10)	0.3107 (2)	0.68985 (6)	0.0289 (3)
H17	0.0687	0.3046	0.7236	0.035*
C18	0.11499 (11)	0.1503 (2)	0.64588 (7)	0.0343 (3)
H18A	0.1664	0.1488	0.6111	0.041*
H18B	0.0585	0.0357	0.6489	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (4)	0.0368 (5)	0.0297 (4)	0.0035 (4)	0.0000 (3)	0.0133 (4)
N1	0.0167 (4)	0.0233 (5)	0.0195 (4)	0.0001 (3)	0.0013 (3)	0.0025 (3)
N2	0.0174 (4)	0.0204 (5)	0.0228 (4)	−0.0012 (3)	−0.0004 (3)	0.0008 (3)
C1	0.0182 (4)	0.0190 (5)	0.0199 (5)	0.0011 (4)	−0.0008 (4)	−0.0002 (4)
C2	0.0184 (5)	0.0245 (6)	0.0272 (5)	−0.0004 (4)	−0.0013 (4)	0.0006 (4)
C3	0.0217 (5)	0.0290 (6)	0.0282 (6)	0.0039 (4)	−0.0060 (4)	−0.0007 (5)
C4	0.0282 (5)	0.0277 (6)	0.0230 (5)	0.0065 (4)	−0.0026 (4)	0.0034 (4)
C5	0.0254 (5)	0.0213 (5)	0.0239 (5)	0.0013 (4)	0.0010 (4)	0.0029 (4)
C6	0.0184 (4)	0.0189 (5)	0.0208 (5)	0.0013 (4)	−0.0007 (4)	−0.0007 (4)
C7	0.0175 (4)	0.0196 (5)	0.0188 (4)	−0.0006 (4)	0.0028 (3)	−0.0006 (4)
C8	0.0194 (5)	0.0184 (5)	0.0244 (5)	0.0001 (4)	0.0024 (4)	−0.0006 (4)
C9	0.0183 (5)	0.0203 (5)	0.0235 (5)	−0.0022 (4)	−0.0011 (4)	0.0019 (4)
C10	0.0175 (4)	0.0231 (5)	0.0200 (5)	0.0003 (4)	0.0011 (4)	0.0015 (4)
C11	0.0225 (5)	0.0236 (6)	0.0245 (5)	−0.0011 (4)	0.0002 (4)	−0.0002 (4)
C12	0.0269 (6)	0.0338 (7)	0.0254 (5)	−0.0077 (5)	−0.0030 (4)	−0.0013 (5)
C13	0.0187 (5)	0.0456 (8)	0.0286 (6)	−0.0047 (5)	−0.0028 (4)	0.0060 (5)
C14	0.0184 (5)	0.0401 (7)	0.0383 (7)	0.0056 (5)	0.0009 (4)	0.0014 (6)
C15	0.0208 (5)	0.0300 (6)	0.0326 (6)	0.0041 (4)	0.0010 (4)	−0.0045 (5)
C16	0.0242 (5)	0.0317 (6)	0.0202 (5)	0.0013 (4)	0.0045 (4)	−0.0019 (4)
C17	0.0203 (5)	0.0373 (7)	0.0294 (6)	0.0004 (5)	0.0044 (4)	0.0088 (5)
C18	0.0283 (6)	0.0298 (7)	0.0447 (7)	−0.0052 (5)	0.0009 (5)	0.0063 (6)

Geometric parameters (Å, º) top

O1—C9	1.2176 (14)	C8—H8B	0.9900
N1—C9	1.3713 (14)	C10—C15	1.3956 (15)
N1—C1	1.4207 (14)	C10—C11	1.3975 (16)
N1—C16	1.4725 (13)	C11—C12	1.3910 (15)
N2—C7	1.2884 (14)	C11—H11	0.9500
N2—C6	1.4041 (13)	C12—C13	1.3898 (19)
C1—C2	1.4038 (14)	C12—H12	0.9500
C1—C6	1.4100 (15)	C13—C14	1.383 (2)
C2—C3	1.3841 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3938 (16)
C3—C4	1.3918 (18)	C14—H14	0.9500
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.3823 (16)	C16—C17	1.4981 (18)
C4—H4	0.9500	C16—H16A	0.9900
C5—C6	1.4040 (15)	C16—H16B	0.9900
C5—H5	0.9500	C17—C18	1.314 (2)
C7—C10	1.4824 (14)	C17—H17	0.9500
C7—C8	1.5133 (15)	C18—H18A	0.9500
C8—C9	1.5164 (15)	C18—H18B	0.9500
C8—H8A	0.9900

C9—N1—C1	123.83 (9)	O1—C9—C8	122.78 (10)
C9—N1—C16	117.57 (9)	N1—C9—C8	114.45 (9)
C1—N1—C16	118.58 (9)	C15—C10—C11	119.22 (10)
C7—N2—C6	120.05 (10)	C15—C10—C7	120.75 (10)
C2—C1—C6	118.97 (10)	C11—C10—C7	120.02 (10)
C2—C1—N1	118.43 (9)	C12—C11—C10	120.11 (11)
C6—C1—N1	122.46 (9)	C12—C11—H11	119.9
C3—C2—C1	121.10 (11)	C10—C11—H11	119.9
C3—C2—H2	119.4	C13—C12—C11	120.31 (12)
C1—C2—H2	119.4	C13—C12—H12	119.8
C2—C3—C4	120.08 (10)	C11—C12—H12	119.8
C2—C3—H3	120.0	C14—C13—C12	119.86 (11)
C4—C3—H3	120.0	C14—C13—H13	120.1
C5—C4—C3	119.50 (11)	C12—C13—H13	120.1
C5—C4—H4	120.2	C13—C14—C15	120.22 (12)
C3—C4—H4	120.2	C13—C14—H14	119.9
C4—C5—C6	121.54 (11)	C15—C14—H14	119.9
C4—C5—H5	119.2	C14—C15—C10	120.26 (12)
C6—C5—H5	119.2	C14—C15—H15	119.9
N2—C6—C5	116.21 (10)	C10—C15—H15	119.9
N2—C6—C1	124.85 (9)	N1—C16—C17	115.57 (10)
C5—C6—C1	118.79 (10)	N1—C16—H16A	108.4
N2—C7—C10	118.19 (10)	C17—C16—H16A	108.4
N2—C7—C8	121.90 (9)	N1—C16—H16B	108.4
C10—C7—C8	119.86 (9)	C17—C16—H16B	108.4
C7—C8—C9	105.22 (9)	H16A—C16—H16B	107.4
C7—C8—H8A	110.7	C18—C17—C16	126.47 (11)
C9—C8—H8A	110.7	C18—C17—H17	116.8
C7—C8—H8B	110.7	C16—C17—H17	116.8
C9—C8—H8B	110.7	C17—C18—H18A	120.0
H8A—C8—H8B	108.8	C17—C18—H18B	120.0
O1—C9—N1	122.69 (10)	H18A—C18—H18B	120.0

C9—N1—C1—C2	138.75 (11)	C1—N1—C9—O1	178.41 (11)
C16—N1—C1—C2	−42.98 (14)	C16—N1—C9—O1	0.11 (17)
C9—N1—C1—C6	−45.56 (16)	C1—N1—C9—C8	1.68 (15)
C16—N1—C1—C6	132.71 (11)	C16—N1—C9—C8	−176.62 (9)
C6—C1—C2—C3	0.28 (17)	C7—C8—C9—O1	−106.66 (12)
N1—C1—C2—C3	176.12 (11)	C7—C8—C9—N1	70.06 (12)
C1—C2—C3—C4	−0.74 (18)	N2—C7—C10—C15	−148.72 (11)
C2—C3—C4—C5	0.15 (18)	C8—C7—C10—C15	33.95 (15)
C3—C4—C5—C6	0.91 (18)	N2—C7—C10—C11	30.35 (15)
C7—N2—C6—C5	−142.10 (11)	C8—C7—C10—C11	−146.97 (11)
C7—N2—C6—C1	42.31 (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—C13	0.45 (18)
C2—C1—C6—N2	176.23 (10)	C11—C12—C13—C14	0.70 (19)
N1—C1—C6—N2	0.56 (17)	C12—C13—C14—C15	−1.5 (2)
C2—C1—C6—C5	0.75 (16)	C13—C14—C15—C10	1.2 (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—C14	179.07 (11)
C6—N2—C7—C8	2.15 (15)	C9—N1—C16—C17	−83.98 (13)
N2—C7—C8—C9	−75.36 (12)	C1—N1—C16—C17	97.64 (12)
C10—C7—C8—C9	101.86 (10)	N1—C16—C17—C18	0.49 (18)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O
M_r	276.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.4863 (3), 6.0053 (2), 20.3667 (5)
β (°)	93.525 (1)
V (Å³)	1402.21 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.41 × 0.33 × 0.15

Data collection
Diffractometer	Bruker X8 APEX2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18220, 4096, 3417
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.153, 1.07
No. of reflections	4096
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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