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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2657.
Published online 2009 October 7. doi:  10.1107/S1600536809039932
PMCID: PMC2971313

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

Abstract

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 [triangle]); Chammache et al. (2001 [triangle]).

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Object name is e-65-o2657-scheme1.jpg

Experimental

Crystal data

  • C17H20N2O2
  • M r = 284.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2657-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039932/tk2546Isup2.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

Experimental

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

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.

Figures

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

Crystal data

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

Bruker APEXII diffractometer3878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 30.5°, θmin = 5.2°
[var phi] and ω scansh = −13→13
27399 measured reflectionsk = 0→20
4591 independent reflectionsl = 0→16

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 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

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

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)
H130.05410.5972−0.01640.040*
C140.01201 (13)0.63481 (9)−0.19226 (11)0.0390 (3)
H14−0.08670.6311−0.19760.047*
C150.07343 (14)0.66027 (9)−0.29194 (10)0.0400 (3)
H150.01640.6734−0.36570.048*
C160.21775 (14)0.66671 (8)−0.28440 (10)0.0365 (2)
H160.25900.6844−0.35270.044*
C170.30146 (12)0.64719 (7)−0.17679 (9)0.0308 (2)
H170.40000.6519−0.17160.037*

Atomic displacement parameters (Å2)

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, °)

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—C12−158.47 (9)
C3—N1—C2—O1−7.51 (14)N2—C9—C10—C1124.81 (16)
C11—N1—C2—C1−16.81 (14)C12—C9—C10—C11−159.20 (10)
C3—N1—C2—C1167.66 (9)C9—C10—C11—O2−174.30 (11)
C2—N1—C3—C481.59 (10)C9—C10—C11—N113.72 (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—O2120.27 (11)
C11—N1—C3—C830.00 (11)C2—N1—C11—C10117.44 (10)
N1—C3—C4—C5−179.46 (9)C3—N1—C11—C10−67.27 (12)
C8—C3—C4—C557.29 (11)N2—C9—C12—C13−138.24 (10)
C3—C4—C5—C6−55.11 (13)C10—C9—C12—C1345.54 (14)
C4—C5—C6—C755.70 (14)N2—C9—C12—C1743.26 (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—C140.29 (16)
C9—N2—C8—C7155.86 (9)C9—C12—C13—C14−178.23 (10)
N1—C3—C8—N252.05 (10)C12—C13—C14—C150.27 (18)
C4—C3—C8—N2176.50 (8)C13—C14—C15—C16−0.56 (19)
N1—C3—C8—C7176.16 (8)C14—C15—C16—C170.29 (18)
C4—C3—C8—C7−59.39 (10)C15—C16—C17—C120.27 (17)
C6—C7—C8—N2−176.16 (8)C13—C12—C17—C16−0.56 (16)
C6—C7—C8—C358.84 (11)C9—C12—C17—C16177.95 (9)
C8—N2—C9—C1017.64 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (1)2.00 (1)2.854 (1)164 (1)

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2546).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chammache, M., Essassi, E. M. & Pierrot, M. (2001). Z. Kristallogr. New Cryst. Struct.216, 101–102.
  • Clark, B. A. J., Evans, M. C., Lloyd, D., McNab, H. & Parsons, S. (1999). Acta Cryst. C55, 1725–1727.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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