1-Acetyl-4-phenyl-5a,6,7,8,9,9a-hexa­hydro-5H-1,5-benzodiazepin-2(1H)-one

Benzeid, H.; Saffon, N.; Garrigues, B.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536809039932

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2657

https://doi.org/10.1107/S1600536809039932

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1-Acetyl-4-phenyl-5a,6,7,8,9,9a-hexahydro-5H-1,5-benzodiazepin-2(1H)-one

Hanane Benzeid,^a Nathalie Saffon,^b Bernard Garrigues,^c El Mokhtar Essassi ^a and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bService Commun Rayons X, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, 31062 Toulouse, France, ^cHétérochimie Fondamentale et Appliquée, Université Paul Sabatier, UMR 5069, 118 Route de Narbonne, 31062 Toulouse, France, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 September 2009; accepted 1 October 2009; online 7 October 2009)

The seven-membered ring of the title compound, C₁₇H₂₀N₂O₂, adopts an approximate boat conformation while the cyclohexyl ring adopts a chair conformation. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into a zigzag chain running along the c axis of the monoclinic unit cell.

Related literature

For the crystal structures of anhydrous and hydrated 7-phenyl-1,2, 3,4-tetrahydro-1,4-diazepin-5-ones, see: Clark et al. (1999 ); Chammache et al. (2001 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₂
M_r = 284.35
Monoclinic, P 2₁ /c
a = 9.6794 (2) Å
b = 14.0095 (3) Å
c = 11.2832 (2) Å
β = 98.053 (1)°
V = 1514.95 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.6 × 0.6 × 0.6 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
27399 measured reflections
4591 independent reflections
3878 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.139
S = 1.05
4591 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.88 (1)	2.001 (9)	2.854 (1)	164 (1)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039932/tk2546sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039932/tk2546Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of anhydrous and hydrated 7-phenyl-1,2, 3,4-tetrahydro-1,4-diazepin-5-ones, see: Clark et al. (1999); Chammache et al. (2001).

Experimental top

4-Phenyl-5a,6,7,8,9,9a-hexahydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1 g) was refluxed in acetic acid (20 ml) for 12 h. The precipate was collected and recrystallized from ethanol to afford colorless crystals in 90% yield.

Structure description top

For the crystal structures of anhydrous and hydrated 7-phenyl-1,2, 3,4-tetrahydro-1,4-diazepin-5-ones, see: Clark et al. (1999); Chammache et al. (2001).

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

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₇H₂₀N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1-Acetyl-4-phenyl-5a,6,7,8,9,9a-hexahydro-5H- 1,5-benzodiazepin-2(1H)-one top

Crystal data top

C₁₇H₂₀N₂O₂	F(000) = 608
M_r = 284.35	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9928 reflections
a = 9.6794 (2) Å	θ = 5.2–30.6°
b = 14.0095 (3) Å	µ = 0.08 mm⁻¹
c = 11.2832 (2) Å	T = 193 K
β = 98.053 (1)°	Block, colorless
V = 1514.95 (5) Å³	0.6 × 0.6 × 0.6 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 30.5°, θ_min = 5.2°
φ and ω scans	h = −13→13
27399 measured reflections	k = 0→20
4591 independent reflections	l = 0→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0824P)² + 0.2971P] where P = (F_o² + 2F_c²)/3
4591 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₂	V = 1514.95 (5) Å³
M_r = 284.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6794 (2) Å	µ = 0.08 mm⁻¹
b = 14.0095 (3) Å	T = 193 K
c = 11.2832 (2) Å	0.6 × 0.6 × 0.6 mm
β = 98.053 (1)°

Data collection top

Bruker APEXII diffractometer	3878 reflections with I > 2σ(I)
27399 measured reflections	R_int = 0.024
4591 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.38 e Å⁻³
4591 reflections	Δρ_min = −0.30 e Å⁻³
195 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.38581 (9)	0.66240 (6)	0.46797 (7)	0.03445 (19)
O2	0.32929 (9)	0.42092 (6)	0.27399 (8)	0.0390 (2)
N1	0.40005 (8)	0.57744 (6)	0.29988 (7)	0.02455 (17)
N2	0.44012 (9)	0.65352 (6)	0.07259 (8)	0.02644 (18)
H2	0.4411 (15)	0.7098 (7)	0.0384 (12)	0.038 (4)*
C1	0.18397 (12)	0.57212 (10)	0.39317 (10)	0.0398 (3)
H1A	0.1299	0.6227	0.4252	0.060*
H1B	0.1843	0.5152	0.4436	0.060*
H1C	0.1417	0.5566	0.3114	0.060*
C2	0.33153 (10)	0.60571 (7)	0.39210 (8)	0.0266 (2)
C3	0.53214 (10)	0.62624 (7)	0.28648 (9)	0.02480 (19)
H3	0.5220	0.6951	0.3071	0.030*
C4	0.65550 (11)	0.58553 (8)	0.37093 (10)	0.0321 (2)
H4A	0.6663	0.5168	0.3538	0.039*
H4B	0.6375	0.5918	0.4548	0.039*
C5	0.78980 (12)	0.63873 (10)	0.35493 (12)	0.0412 (3)
H5A	0.8697	0.6087	0.4059	0.049*
H5B	0.7828	0.7058	0.3812	0.049*
C6	0.81573 (12)	0.63687 (9)	0.22446 (12)	0.0382 (3)
H6A	0.8330	0.5703	0.2009	0.046*
H6B	0.8999	0.6750	0.2160	0.046*
C7	0.69074 (11)	0.67727 (8)	0.14134 (10)	0.0322 (2)
H7A	0.7086	0.6732	0.0572	0.039*
H7B	0.6774	0.7453	0.1607	0.039*
C8	0.55891 (10)	0.62073 (7)	0.15649 (9)	0.02496 (19)
H8	0.5762	0.5523	0.1379	0.030*
C9	0.33011 (10)	0.59655 (7)	0.03819 (8)	0.02568 (19)
C10	0.30297 (11)	0.51532 (7)	0.10041 (9)	0.0280 (2)
H10	0.2498	0.4668	0.0563	0.034*
C11	0.34703 (10)	0.49695 (7)	0.22489 (9)	0.02630 (19)
C12	0.24115 (11)	0.62065 (7)	−0.07600 (9)	0.0269 (2)
C13	0.09583 (12)	0.61485 (8)	−0.08454 (10)	0.0333 (2)
H13	0.0541	0.5972	−0.0164	0.040*
C14	0.01201 (13)	0.63481 (9)	−0.19226 (11)	0.0390 (3)
H14	−0.0867	0.6311	−0.1976	0.047*
C15	0.07343 (14)	0.66027 (9)	−0.29194 (10)	0.0400 (3)
H15	0.0164	0.6734	−0.3657	0.048*
C16	0.21775 (14)	0.66671 (8)	−0.28440 (10)	0.0365 (2)
H16	0.2590	0.6844	−0.3527	0.044*
C17	0.30146 (12)	0.64719 (7)	−0.17679 (9)	0.0308 (2)
H17	0.4000	0.6519	−0.1716	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0456 (5)	0.0305 (4)	0.0279 (4)	−0.0012 (3)	0.0075 (3)	−0.0051 (3)
O2	0.0502 (5)	0.0266 (4)	0.0384 (4)	−0.0081 (3)	−0.0005 (4)	0.0075 (3)
N1	0.0264 (4)	0.0238 (4)	0.0234 (4)	−0.0018 (3)	0.0033 (3)	−0.0015 (3)
N2	0.0308 (4)	0.0209 (4)	0.0275 (4)	−0.0017 (3)	0.0038 (3)	0.0017 (3)
C1	0.0286 (5)	0.0589 (7)	0.0326 (5)	−0.0009 (5)	0.0063 (4)	0.0009 (5)
C2	0.0301 (5)	0.0263 (4)	0.0236 (4)	0.0030 (3)	0.0038 (3)	0.0026 (3)
C3	0.0256 (4)	0.0214 (4)	0.0273 (4)	−0.0012 (3)	0.0034 (3)	−0.0019 (3)
C4	0.0281 (5)	0.0344 (5)	0.0324 (5)	0.0006 (4)	−0.0010 (4)	−0.0002 (4)
C5	0.0286 (5)	0.0494 (7)	0.0440 (6)	−0.0053 (5)	−0.0006 (4)	−0.0051 (5)
C6	0.0272 (5)	0.0390 (6)	0.0492 (7)	−0.0038 (4)	0.0080 (4)	−0.0051 (5)
C7	0.0314 (5)	0.0278 (5)	0.0387 (5)	−0.0050 (4)	0.0096 (4)	−0.0028 (4)
C8	0.0258 (4)	0.0208 (4)	0.0286 (4)	−0.0003 (3)	0.0049 (3)	−0.0016 (3)
C9	0.0310 (5)	0.0233 (4)	0.0229 (4)	−0.0006 (3)	0.0047 (3)	−0.0026 (3)
C10	0.0357 (5)	0.0228 (4)	0.0251 (4)	−0.0053 (3)	0.0030 (4)	−0.0028 (3)
C11	0.0290 (4)	0.0219 (4)	0.0277 (4)	−0.0014 (3)	0.0029 (3)	−0.0005 (3)
C12	0.0326 (5)	0.0246 (4)	0.0235 (4)	−0.0022 (3)	0.0036 (3)	−0.0012 (3)
C13	0.0335 (5)	0.0366 (5)	0.0300 (5)	−0.0015 (4)	0.0056 (4)	0.0012 (4)
C14	0.0347 (5)	0.0422 (6)	0.0383 (6)	0.0006 (4)	−0.0006 (4)	0.0002 (5)
C15	0.0506 (7)	0.0390 (6)	0.0277 (5)	0.0019 (5)	−0.0041 (5)	−0.0006 (4)
C16	0.0519 (7)	0.0348 (5)	0.0233 (4)	−0.0036 (5)	0.0067 (4)	−0.0006 (4)
C17	0.0383 (5)	0.0283 (5)	0.0263 (4)	−0.0042 (4)	0.0065 (4)	−0.0023 (4)

Geometric parameters (Å, º) top

O1—C2	1.2303 (13)	C6—H6A	0.9900
O2—C11	1.2238 (12)	C6—H6B	0.9900
N1—C2	1.3686 (12)	C7—C8	1.5317 (14)
N1—C11	1.4591 (12)	C7—H7A	0.9900
N1—C3	1.4761 (12)	C7—H7B	0.9900
N2—C9	1.3438 (13)	C8—H8	1.0000
N2—C8	1.4574 (13)	C9—C10	1.3815 (13)
N2—H2	0.878 (9)	C9—C12	1.4849 (14)
C1—C2	1.5055 (15)	C10—C11	1.4328 (14)
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800	C12—C13	1.3987 (15)
C1—H1C	0.9800	C12—C17	1.3995 (14)
C3—C4	1.5298 (14)	C13—C14	1.3919 (16)
C3—C8	1.5268 (13)	C13—H13	0.9500
C3—H3	1.0000	C14—C15	1.3904 (17)
C4—C5	1.5309 (16)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.3904 (19)
C4—H4B	0.9900	C15—H15	0.9500
C5—C6	1.5279 (18)	C16—C17	1.3892 (16)
C5—H5A	0.9900	C16—H16	0.9500
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.5315 (17)

C2—N1—C11	119.73 (8)	C6—C7—C8	109.85 (9)
C2—N1—C3	117.57 (8)	C6—C7—H7A	109.7
C11—N1—C3	122.54 (8)	C8—C7—H7A	109.7
C9—N2—C8	121.44 (8)	C6—C7—H7B	109.7
C9—N2—H2	117.6 (10)	C8—C7—H7B	109.7
C8—N2—H2	120.8 (10)	H7A—C7—H7B	108.2
C2—C1—H1A	109.5	N2—C8—C3	112.54 (8)
C2—C1—H1B	109.5	N2—C8—C7	111.00 (8)
H1A—C1—H1B	109.5	C3—C8—C7	109.71 (8)
C2—C1—H1C	109.5	N2—C8—H8	107.8
H1A—C1—H1C	109.5	C3—C8—H8	107.8
H1B—C1—H1C	109.5	C7—C8—H8	107.8
O1—C2—N1	120.71 (9)	N2—C9—C10	122.81 (9)
O1—C2—C1	120.62 (9)	N2—C9—C12	117.08 (8)
N1—C2—C1	118.49 (9)	C10—C9—C12	119.99 (9)
N1—C3—C4	112.03 (8)	C9—C10—C11	126.47 (9)
N1—C3—C8	109.94 (7)	C9—C10—H10	116.8
C4—C3—C8	110.90 (8)	C11—C10—H10	116.8
N1—C3—H3	107.9	O2—C11—C10	123.97 (9)
C4—C3—H3	107.9	O2—C11—N1	118.06 (9)
C8—C3—H3	107.9	C10—C11—N1	117.51 (8)
C3—C4—C5	110.28 (9)	C13—C12—C17	119.30 (10)
C3—C4—H4A	109.6	C13—C12—C9	120.13 (9)
C5—C4—H4A	109.6	C17—C12—C9	120.55 (9)
C3—C4—H4B	109.6	C14—C13—C12	120.40 (10)
C5—C4—H4B	109.6	C14—C13—H13	119.8
H4A—C4—H4B	108.1	C12—C13—H13	119.8
C4—C5—C6	111.23 (10)	C15—C14—C13	119.66 (11)
C4—C5—H5A	109.4	C15—C14—H14	120.2
C6—C5—H5A	109.4	C13—C14—H14	120.2
C4—C5—H5B	109.4	C14—C15—C16	120.46 (11)
C6—C5—H5B	109.4	C14—C15—H15	119.8
H5A—C5—H5B	108.0	C16—C15—H15	119.8
C5—C6—C7	111.19 (9)	C17—C16—C15	119.92 (10)
C5—C6—H6A	109.4	C17—C16—H16	120.0
C7—C6—H6A	109.4	C15—C16—H16	120.0
C5—C6—H6B	109.4	C16—C17—C12	120.26 (11)
C7—C6—H6B	109.4	C16—C17—H17	119.9
H6A—C6—H6B	108.0	C12—C17—H17	119.9

C11—N1—C2—O1	168.01 (9)	C8—N2—C9—C12	−158.47 (9)
C3—N1—C2—O1	−7.51 (14)	N2—C9—C10—C11	24.81 (16)
C11—N1—C2—C1	−16.81 (14)	C12—C9—C10—C11	−159.20 (10)
C3—N1—C2—C1	167.66 (9)	C9—C10—C11—O2	−174.30 (11)
C2—N1—C3—C4	81.59 (10)	C9—C10—C11—N1	13.72 (15)
C11—N1—C3—C4	−93.80 (10)	C2—N1—C11—O2	−55.02 (13)
C2—N1—C3—C8	−154.61 (8)	C3—N1—C11—O2	120.27 (11)
C11—N1—C3—C8	30.00 (11)	C2—N1—C11—C10	117.44 (10)
N1—C3—C4—C5	−179.46 (9)	C3—N1—C11—C10	−67.27 (12)
C8—C3—C4—C5	57.29 (11)	N2—C9—C12—C13	−138.24 (10)
C3—C4—C5—C6	−55.11 (13)	C10—C9—C12—C13	45.54 (14)
C4—C5—C6—C7	55.70 (14)	N2—C9—C12—C17	43.26 (13)
C5—C6—C7—C8	−57.34 (12)	C10—C9—C12—C17	−132.96 (10)
C9—N2—C8—C3	−80.75 (11)	C17—C12—C13—C14	0.29 (16)
C9—N2—C8—C7	155.86 (9)	C9—C12—C13—C14	−178.23 (10)
N1—C3—C8—N2	52.05 (10)	C12—C13—C14—C15	0.27 (18)
C4—C3—C8—N2	176.50 (8)	C13—C14—C15—C16	−0.56 (19)
N1—C3—C8—C7	176.16 (8)	C14—C15—C16—C17	0.29 (18)
C4—C3—C8—C7	−59.39 (10)	C15—C16—C17—C12	0.27 (17)
C6—C7—C8—N2	−176.16 (8)	C13—C12—C17—C16	−0.56 (16)
C6—C7—C8—C3	58.84 (11)	C9—C12—C17—C16	177.95 (9)
C8—N2—C9—C10	17.64 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.88 (1)	2.00 (1)	2.854 (1)	164 (1)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₂
M_r	284.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	9.6794 (2), 14.0095 (3), 11.2832 (2)
β (°)	98.053 (1)
V (Å³)	1514.95 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.6 × 0.6 × 0.6

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27399, 4591, 3878
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.139, 1.05
No. of reflections	4591
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.88 (1)	2.001 (9)	2.854 (1)	164 (1)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

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

References

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