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

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ISSN: 2056-9890

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

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[Clark, B. A. J., Evans, M. C., Lloyd, D., McNab, H. & Parsons, S. (1999). Acta Cryst. C55, 1725-1727.]); Chammache et al. (2001[Chammache, M., Essassi, E. M. & Pierrot, M. (2001). Z. Kristallogr. New Cryst. Struct. 216, 101-102.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20N2O2

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[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 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The amino H-atom was located in a difference Fourier map and was refined with an N–H 0.88±0.01 Å restraint.

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
[Figure 1] 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
C17H20N2O2F(000) = 608
Mr = 284.35Dx = 1.247 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9928 reflections
a = 9.6794 (2) Åθ = 5.2–30.6°
b = 14.0095 (3) ŵ = 0.08 mm1
c = 11.2832 (2) ÅT = 193 K
β = 98.053 (1)°Block, colorless
V = 1514.95 (5) Å30.6 × 0.6 × 0.6 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
3878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 30.5°, θmin = 5.2°
φ and ω scansh = 1313
27399 measured reflectionsk = 020
4591 independent reflectionsl = 016
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0824P)2 + 0.2971P]
where P = (Fo2 + 2Fc2)/3
4591 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.38 e Å3
1 restraintΔρmin = 0.30 e Å3
Crystal data top
C17H20N2O2V = 1514.95 (5) Å3
Mr = 284.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6794 (2) ŵ = 0.08 mm1
b = 14.0095 (3) ÅT = 193 K
c = 11.2832 (2) Å0.6 × 0.6 × 0.6 mm
β = 98.053 (1)°
Data collection top
Bruker APEXII
diffractometer
3878 reflections with I > 2σ(I)
27399 measured reflectionsRint = 0.024
4591 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.38 e Å3
4591 reflectionsΔρmin = 0.30 e Å3
195 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.38581 (9)0.66240 (6)0.46797 (7)0.03445 (19)
O20.32929 (9)0.42092 (6)0.27399 (8)0.0390 (2)
N10.40005 (8)0.57744 (6)0.29988 (7)0.02455 (17)
N20.44012 (9)0.65352 (6)0.07259 (8)0.02644 (18)
H20.4411 (15)0.7098 (7)0.0384 (12)0.038 (4)*
C10.18397 (12)0.57212 (10)0.39317 (10)0.0398 (3)
H1A0.12990.62270.42520.060*
H1B0.18430.51520.44360.060*
H1C0.14170.55660.31140.060*
C20.33153 (10)0.60571 (7)0.39210 (8)0.0266 (2)
C30.53214 (10)0.62624 (7)0.28648 (9)0.02480 (19)
H30.52200.69510.30710.030*
C40.65550 (11)0.58553 (8)0.37093 (10)0.0321 (2)
H4A0.66630.51680.35380.039*
H4B0.63750.59180.45480.039*
C50.78980 (12)0.63873 (10)0.35493 (12)0.0412 (3)
H5A0.86970.60870.40590.049*
H5B0.78280.70580.38120.049*
C60.81573 (12)0.63687 (9)0.22446 (12)0.0382 (3)
H6A0.83300.57030.20090.046*
H6B0.89990.67500.21600.046*
C70.69074 (11)0.67727 (8)0.14134 (10)0.0322 (2)
H7A0.70860.67320.05720.039*
H7B0.67740.74530.16070.039*
C80.55891 (10)0.62073 (7)0.15649 (9)0.02496 (19)
H80.57620.55230.13790.030*
C90.33011 (10)0.59655 (7)0.03819 (8)0.02568 (19)
C100.30297 (11)0.51532 (7)0.10041 (9)0.0280 (2)
H100.24980.46680.05630.034*
C110.34703 (10)0.49695 (7)0.22489 (9)0.02630 (19)
C120.24115 (11)0.62065 (7)0.07600 (9)0.0269 (2)
C130.09583 (12)0.61485 (8)0.08454 (10)0.0333 (2)
H130.05410.59720.01640.040*
C140.01201 (13)0.63481 (9)0.19226 (11)0.0390 (3)
H140.08670.63110.19760.047*
C150.07343 (14)0.66027 (9)0.29194 (10)0.0400 (3)
H150.01640.67340.36570.048*
C160.21775 (14)0.66671 (8)0.28440 (10)0.0365 (2)
H160.25900.68440.35270.044*
C170.30146 (12)0.64719 (7)0.17679 (9)0.0308 (2)
H170.40000.65190.17160.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0456 (5)0.0305 (4)0.0279 (4)0.0012 (3)0.0075 (3)0.0051 (3)
O20.0502 (5)0.0266 (4)0.0384 (4)0.0081 (3)0.0005 (4)0.0075 (3)
N10.0264 (4)0.0238 (4)0.0234 (4)0.0018 (3)0.0033 (3)0.0015 (3)
N20.0308 (4)0.0209 (4)0.0275 (4)0.0017 (3)0.0038 (3)0.0017 (3)
C10.0286 (5)0.0589 (7)0.0326 (5)0.0009 (5)0.0063 (4)0.0009 (5)
C20.0301 (5)0.0263 (4)0.0236 (4)0.0030 (3)0.0038 (3)0.0026 (3)
C30.0256 (4)0.0214 (4)0.0273 (4)0.0012 (3)0.0034 (3)0.0019 (3)
C40.0281 (5)0.0344 (5)0.0324 (5)0.0006 (4)0.0010 (4)0.0002 (4)
C50.0286 (5)0.0494 (7)0.0440 (6)0.0053 (5)0.0006 (4)0.0051 (5)
C60.0272 (5)0.0390 (6)0.0492 (7)0.0038 (4)0.0080 (4)0.0051 (5)
C70.0314 (5)0.0278 (5)0.0387 (5)0.0050 (4)0.0096 (4)0.0028 (4)
C80.0258 (4)0.0208 (4)0.0286 (4)0.0003 (3)0.0049 (3)0.0016 (3)
C90.0310 (5)0.0233 (4)0.0229 (4)0.0006 (3)0.0047 (3)0.0026 (3)
C100.0357 (5)0.0228 (4)0.0251 (4)0.0053 (3)0.0030 (4)0.0028 (3)
C110.0290 (4)0.0219 (4)0.0277 (4)0.0014 (3)0.0029 (3)0.0005 (3)
C120.0326 (5)0.0246 (4)0.0235 (4)0.0022 (3)0.0036 (3)0.0012 (3)
C130.0335 (5)0.0366 (5)0.0300 (5)0.0015 (4)0.0056 (4)0.0012 (4)
C140.0347 (5)0.0422 (6)0.0383 (6)0.0006 (4)0.0006 (4)0.0002 (5)
C150.0506 (7)0.0390 (6)0.0277 (5)0.0019 (5)0.0041 (5)0.0006 (4)
C160.0519 (7)0.0348 (5)0.0233 (4)0.0036 (5)0.0067 (4)0.0006 (4)
C170.0383 (5)0.0283 (5)0.0263 (4)0.0042 (4)0.0065 (4)0.0023 (4)
Geometric parameters (Å, º) top
O1—C21.2303 (13)C6—H6A0.9900
O2—C111.2238 (12)C6—H6B0.9900
N1—C21.3686 (12)C7—C81.5317 (14)
N1—C111.4591 (12)C7—H7A0.9900
N1—C31.4761 (12)C7—H7B0.9900
N2—C91.3438 (13)C8—H81.0000
N2—C81.4574 (13)C9—C101.3815 (13)
N2—H20.878 (9)C9—C121.4849 (14)
C1—C21.5055 (15)C10—C111.4328 (14)
C1—H1A0.9800C10—H100.9500
C1—H1B0.9800C12—C131.3987 (15)
C1—H1C0.9800C12—C171.3995 (14)
C3—C41.5298 (14)C13—C141.3919 (16)
C3—C81.5268 (13)C13—H130.9500
C3—H31.0000C14—C151.3904 (17)
C4—C51.5309 (16)C14—H140.9500
C4—H4A0.9900C15—C161.3904 (19)
C4—H4B0.9900C15—H150.9500
C5—C61.5279 (18)C16—C171.3892 (16)
C5—H5A0.9900C16—H160.9500
C5—H5B0.9900C17—H170.9500
C6—C71.5315 (17)
C2—N1—C11119.73 (8)C6—C7—C8109.85 (9)
C2—N1—C3117.57 (8)C6—C7—H7A109.7
C11—N1—C3122.54 (8)C8—C7—H7A109.7
C9—N2—C8121.44 (8)C6—C7—H7B109.7
C9—N2—H2117.6 (10)C8—C7—H7B109.7
C8—N2—H2120.8 (10)H7A—C7—H7B108.2
C2—C1—H1A109.5N2—C8—C3112.54 (8)
C2—C1—H1B109.5N2—C8—C7111.00 (8)
H1A—C1—H1B109.5C3—C8—C7109.71 (8)
C2—C1—H1C109.5N2—C8—H8107.8
H1A—C1—H1C109.5C3—C8—H8107.8
H1B—C1—H1C109.5C7—C8—H8107.8
O1—C2—N1120.71 (9)N2—C9—C10122.81 (9)
O1—C2—C1120.62 (9)N2—C9—C12117.08 (8)
N1—C2—C1118.49 (9)C10—C9—C12119.99 (9)
N1—C3—C4112.03 (8)C9—C10—C11126.47 (9)
N1—C3—C8109.94 (7)C9—C10—H10116.8
C4—C3—C8110.90 (8)C11—C10—H10116.8
N1—C3—H3107.9O2—C11—C10123.97 (9)
C4—C3—H3107.9O2—C11—N1118.06 (9)
C8—C3—H3107.9C10—C11—N1117.51 (8)
C3—C4—C5110.28 (9)C13—C12—C17119.30 (10)
C3—C4—H4A109.6C13—C12—C9120.13 (9)
C5—C4—H4A109.6C17—C12—C9120.55 (9)
C3—C4—H4B109.6C14—C13—C12120.40 (10)
C5—C4—H4B109.6C14—C13—H13119.8
H4A—C4—H4B108.1C12—C13—H13119.8
C4—C5—C6111.23 (10)C15—C14—C13119.66 (11)
C4—C5—H5A109.4C15—C14—H14120.2
C6—C5—H5A109.4C13—C14—H14120.2
C4—C5—H5B109.4C14—C15—C16120.46 (11)
C6—C5—H5B109.4C14—C15—H15119.8
H5A—C5—H5B108.0C16—C15—H15119.8
C5—C6—C7111.19 (9)C17—C16—C15119.92 (10)
C5—C6—H6A109.4C17—C16—H16120.0
C7—C6—H6A109.4C15—C16—H16120.0
C5—C6—H6B109.4C16—C17—C12120.26 (11)
C7—C6—H6B109.4C16—C17—H17119.9
H6A—C6—H6B108.0C12—C17—H17119.9
C11—N1—C2—O1168.01 (9)C8—N2—C9—C12158.47 (9)
C3—N1—C2—O17.51 (14)N2—C9—C10—C1124.81 (16)
C11—N1—C2—C116.81 (14)C12—C9—C10—C11159.20 (10)
C3—N1—C2—C1167.66 (9)C9—C10—C11—O2174.30 (11)
C2—N1—C3—C481.59 (10)C9—C10—C11—N113.72 (15)
C11—N1—C3—C493.80 (10)C2—N1—C11—O255.02 (13)
C2—N1—C3—C8154.61 (8)C3—N1—C11—O2120.27 (11)
C11—N1—C3—C830.00 (11)C2—N1—C11—C10117.44 (10)
N1—C3—C4—C5179.46 (9)C3—N1—C11—C1067.27 (12)
C8—C3—C4—C557.29 (11)N2—C9—C12—C13138.24 (10)
C3—C4—C5—C655.11 (13)C10—C9—C12—C1345.54 (14)
C4—C5—C6—C755.70 (14)N2—C9—C12—C1743.26 (13)
C5—C6—C7—C857.34 (12)C10—C9—C12—C17132.96 (10)
C9—N2—C8—C380.75 (11)C17—C12—C13—C140.29 (16)
C9—N2—C8—C7155.86 (9)C9—C12—C13—C14178.23 (10)
N1—C3—C8—N252.05 (10)C12—C13—C14—C150.27 (18)
C4—C3—C8—N2176.50 (8)C13—C14—C15—C160.56 (19)
N1—C3—C8—C7176.16 (8)C14—C15—C16—C170.29 (18)
C4—C3—C8—C759.39 (10)C15—C16—C17—C120.27 (17)
C6—C7—C8—N2176.16 (8)C13—C12—C17—C160.56 (16)
C6—C7—C8—C358.84 (11)C9—C12—C17—C16177.95 (9)
C8—N2—C9—C1017.64 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (1)2.00 (1)2.854 (1)164 (1)
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC17H20N2O2
Mr284.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)9.6794 (2), 14.0095 (3), 11.2832 (2)
β (°) 98.053 (1)
V3)1514.95 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.6 × 0.6 × 0.6
Data collection
DiffractometerBruker APEXII
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
27399, 4591, 3878
Rint0.024
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.139, 1.05
No. of reflections4591
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (1)2.001 (9)2.854 (1)164 (1)
Symmetry code: (i) x, y+3/2, z1/2.
 

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 citationChammache, M., Essassi, E. M. & Pierrot, M. (2001). Z. Kristallogr. New Cryst. Struct. 216, 101–102.  CAS Google Scholar
First citationClark, B. A. J., Evans, M. C., Lloyd, D., McNab, H. & Parsons, S. (1999). Acta Cryst. C55, 1725–1727.  Web of Science CSD CrossRef CAS IUCr Journals 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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