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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2070.
Published online 2010 July 21. doi:  10.1107/S1600536810028278
PMCID: PMC3007495

Ethyl 2-(2-oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetate

Abstract

The seven-membered ring in the title compound, C19H18N2O3, adopts a boat conformation with the two phenyl­ene C atoms representing the stern and the methyl­ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring (r.m.s deviation = 0.343 Å) and the phenyl substituent is 31.9 (1)°. The dihedral angle between this best plane and the best plane through the eth­oxy­carbonyl­methyl substituent (r.m.s. deviation = 0.058 Å) is 72.2 (1)°.

Related literature

For the background to 2,3-dihydro-1H-1,5-benzodiazepin-2-ones, see: Ahabchane et al. (1999 [triangle]). For a related structure, see: Ballo et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2070-scheme1.jpg

Experimental

Crystal data

  • C19H18N2O3
  • M r = 322.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2070-efi1.jpg
  • a = 12.5198 (4) Å
  • b = 11.7911 (3) Å
  • c = 11.2058 (3) Å
  • β = 97.843 (2)°
  • V = 1638.75 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.30 × 0.15 × 0.10 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 13943 measured reflections
  • 3029 independent reflections
  • 2195 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.114
  • S = 1.00
  • 3029 reflections
  • 217 parameters
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028278/zs2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028278/zs2051Isup2.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

Comment

The background to the class of 2,3-dihydro-1H-1,5-benzodiazepin-2-ones is given in an earlier report (Ahabchane et al., 1999). A recent study presents the crystal structure of 1-allyl-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one (Ballo et al., 2010). The present study has an ethoxycarbonylmethyl group in place of the allyl group (Scheme I, Fig. 1). The principal feature is the seven-membered ring that is fused to a phenylene ring. This ring adopts a boat-shaped conformation, two phenylene carbons representing the stern and the methylene carbon atom the prow [r.m.s deviation 0.343 Å]. The methyl carbon deviates by 0.604 Å from the best plane.

Experimental

To a solution of 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one (1 g, 4.2 mmol) in DMF (20 ml) was added ethyl chloroacetate (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 yellow crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the molecule of C19H18N2O3 at the 50% probability level.

Crystal data

C19H18N2O3F(000) = 680
Mr = 322.35Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3291 reflections
a = 12.5198 (4) Åθ = 2.4–23.1°
b = 11.7911 (3) ŵ = 0.09 mm1
c = 11.2058 (3) ÅT = 293 K
β = 97.843 (2)°Prism, yellow
V = 1638.75 (8) Å30.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer2195 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
graphiteθmax = 25.5°, θmin = 2.5°
[var phi] and ω scansh = −15→15
13943 measured reflectionsk = −14→14
3029 independent reflectionsl = −13→13

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
3029 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = −0.15 e Å3

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

xyzUiso*/Ueq
O10.45383 (9)0.67927 (10)0.34251 (11)0.0662 (4)
O20.43414 (9)0.64804 (9)0.06491 (11)0.0604 (3)
O30.60915 (8)0.69533 (8)0.08966 (10)0.0488 (3)
N10.39095 (10)0.82128 (10)0.21765 (12)0.0460 (3)
N20.16060 (9)0.76218 (10)0.14862 (11)0.0438 (3)
C10.15443 (12)0.57820 (13)0.23365 (13)0.0452 (4)
C20.21662 (14)0.49224 (14)0.29222 (16)0.0599 (5)
H20.28220.50970.33810.072*
C30.18218 (17)0.38119 (15)0.28306 (18)0.0690 (5)
H30.22530.32420.32140.083*
C40.08518 (16)0.35429 (14)0.21804 (18)0.0648 (5)
H40.06180.27930.21320.078*
C50.02215 (14)0.43823 (15)0.15974 (18)0.0631 (5)
H5−0.04400.42020.11560.076*
C60.05711 (13)0.54944 (13)0.16671 (15)0.0525 (4)
H60.01470.60570.12590.063*
C70.19264 (11)0.69709 (12)0.23782 (13)0.0423 (4)
C80.27085 (12)0.73756 (13)0.34441 (13)0.0483 (4)
H8A0.24970.81180.37020.058*
H8B0.27150.68530.41130.058*
C90.38018 (12)0.74323 (13)0.30496 (14)0.0478 (4)
C100.49294 (13)0.81974 (13)0.16772 (16)0.0536 (4)
H10A0.55230.82880.23230.064*
H10B0.49480.88280.11240.064*
C110.50622 (12)0.71043 (12)0.10251 (13)0.0431 (4)
C120.63354 (14)0.59312 (14)0.02606 (16)0.0592 (5)
H12A0.60500.5992−0.05860.071*
H12B0.60100.52770.05930.071*
C130.75293 (14)0.58019 (15)0.04048 (16)0.0669 (5)
H13A0.77120.5132−0.00110.100*
H13B0.78030.57360.12450.100*
H13C0.78430.64530.00740.100*
C140.31063 (11)0.90246 (12)0.17520 (12)0.0414 (4)
C150.34293 (13)1.01399 (12)0.15912 (14)0.0511 (4)
H150.41531.03330.17760.061*
C160.26962 (15)1.09539 (14)0.11653 (16)0.0595 (5)
H160.29241.16940.10660.071*
C170.16234 (15)1.06815 (14)0.08833 (15)0.0596 (5)
H170.11251.12380.06040.072*
C180.12908 (13)0.95835 (13)0.10160 (14)0.0528 (4)
H180.05660.94020.08100.063*
C190.20182 (12)0.87328 (12)0.14543 (12)0.0418 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0551 (8)0.0761 (8)0.0638 (8)0.0232 (6)−0.0050 (6)0.0014 (6)
O20.0439 (7)0.0632 (7)0.0729 (8)−0.0078 (6)0.0036 (5)−0.0194 (6)
O30.0384 (6)0.0511 (6)0.0573 (7)0.0031 (4)0.0083 (5)−0.0115 (5)
N10.0373 (7)0.0501 (7)0.0512 (8)0.0040 (5)0.0081 (6)−0.0036 (6)
N20.0392 (7)0.0486 (7)0.0432 (7)0.0003 (5)0.0037 (5)0.0044 (6)
C10.0456 (9)0.0518 (9)0.0405 (9)0.0050 (7)0.0138 (7)0.0039 (7)
C20.0617 (11)0.0583 (11)0.0589 (11)0.0074 (8)0.0049 (8)0.0115 (8)
C30.0826 (14)0.0581 (11)0.0687 (12)0.0148 (10)0.0184 (10)0.0180 (9)
C40.0781 (13)0.0476 (10)0.0750 (13)−0.0020 (9)0.0333 (10)0.0026 (9)
C50.0538 (11)0.0612 (11)0.0772 (13)−0.0070 (8)0.0189 (9)−0.0040 (9)
C60.0464 (9)0.0532 (9)0.0594 (10)0.0026 (7)0.0123 (7)0.0050 (8)
C70.0364 (8)0.0518 (9)0.0398 (8)0.0053 (6)0.0088 (6)0.0034 (7)
C80.0523 (10)0.0549 (9)0.0372 (8)0.0053 (7)0.0047 (7)0.0028 (7)
C90.0441 (9)0.0546 (9)0.0421 (9)0.0077 (7)−0.0031 (7)−0.0086 (7)
C100.0390 (9)0.0538 (9)0.0696 (11)−0.0012 (7)0.0129 (8)−0.0137 (8)
C110.0364 (8)0.0487 (8)0.0433 (9)0.0009 (7)0.0025 (6)−0.0019 (7)
C120.0610 (11)0.0597 (10)0.0570 (11)0.0105 (8)0.0082 (8)−0.0162 (8)
C130.0651 (12)0.0721 (12)0.0681 (12)0.0205 (9)0.0253 (9)0.0010 (9)
C140.0413 (8)0.0456 (8)0.0383 (8)0.0031 (6)0.0085 (6)−0.0049 (6)
C150.0521 (10)0.0487 (9)0.0536 (10)−0.0049 (7)0.0108 (7)−0.0090 (7)
C160.0766 (13)0.0426 (9)0.0599 (11)−0.0012 (8)0.0115 (9)−0.0004 (8)
C170.0711 (12)0.0516 (10)0.0552 (10)0.0119 (9)0.0053 (9)0.0088 (8)
C180.0480 (9)0.0592 (10)0.0498 (10)0.0056 (7)0.0019 (7)0.0078 (8)
C190.0430 (8)0.0473 (8)0.0349 (8)0.0009 (7)0.0050 (6)−0.0007 (6)

Geometric parameters (Å, °)

O1—C91.2207 (17)C8—C91.496 (2)
O2—C111.1955 (17)C8—H8A0.9700
O3—C111.3281 (17)C8—H8B0.9700
O3—C121.4537 (17)C10—C111.502 (2)
N1—C91.363 (2)C10—H10A0.9700
N1—C141.4224 (17)C10—H10B0.9700
N1—C101.4625 (19)C12—C131.489 (2)
N2—C71.2805 (18)C12—H12A0.9700
N2—C191.4102 (18)C12—H12B0.9700
C1—C61.383 (2)C13—H13A0.9600
C1—C21.387 (2)C13—H13B0.9600
C1—C71.480 (2)C13—H13C0.9600
C2—C31.378 (2)C14—C151.395 (2)
C2—H20.9300C14—C191.4005 (19)
C3—C41.366 (3)C15—C161.368 (2)
C3—H30.9300C15—H150.9300
C4—C51.374 (2)C16—C171.375 (2)
C4—H40.9300C16—H160.9300
C5—C61.381 (2)C17—C181.374 (2)
C5—H50.9300C17—H170.9300
C6—H60.9300C18—C191.398 (2)
C7—C81.515 (2)C18—H180.9300
C11—O3—C12115.86 (12)C11—C10—H10A109.5
C9—N1—C14124.03 (13)N1—C10—H10B109.5
C9—N1—C10116.31 (12)C11—C10—H10B109.5
C14—N1—C10119.65 (12)H10A—C10—H10B108.0
C7—N2—C19119.99 (13)O2—C11—O3125.19 (14)
C6—C1—C2118.26 (15)O2—C11—C10124.83 (14)
C6—C1—C7120.43 (14)O3—C11—C10109.95 (12)
C2—C1—C7121.26 (14)O3—C12—C13107.85 (13)
C3—C2—C1120.61 (17)O3—C12—H12A110.1
C3—C2—H2119.7C13—C12—H12A110.1
C1—C2—H2119.7O3—C12—H12B110.1
C4—C3—C2120.46 (17)C13—C12—H12B110.1
C4—C3—H3119.8H12A—C12—H12B108.4
C2—C3—H3119.8C12—C13—H13A109.5
C3—C4—C5119.83 (17)C12—C13—H13B109.5
C3—C4—H4120.1H13A—C13—H13B109.5
C5—C4—H4120.1C12—C13—H13C109.5
C4—C5—C6119.99 (17)H13A—C13—H13C109.5
C4—C5—H5120.0H13B—C13—H13C109.5
C6—C5—H5120.0C15—C14—C19119.38 (13)
C5—C6—C1120.83 (16)C15—C14—N1118.26 (13)
C5—C6—H6119.6C19—C14—N1122.32 (13)
C1—C6—H6119.6C16—C15—C14120.93 (16)
N2—C7—C1118.53 (13)C16—C15—H15119.5
N2—C7—C8121.78 (13)C14—C15—H15119.5
C1—C7—C8119.65 (13)C15—C16—C17120.26 (15)
C9—C8—C7107.47 (12)C15—C16—H16119.9
C9—C8—H8A110.2C17—C16—H16119.9
C7—C8—H8A110.2C18—C17—C16119.74 (16)
C9—C8—H8B110.2C18—C17—H17120.1
C7—C8—H8B110.2C16—C17—H17120.1
H8A—C8—H8B108.5C17—C18—C19121.43 (16)
O1—C9—N1121.36 (15)C17—C18—H18119.3
O1—C9—C8123.30 (15)C19—C18—H18119.3
N1—C9—C8115.23 (13)C18—C19—C14118.24 (13)
N1—C10—C11110.92 (12)C18—C19—N2116.89 (13)
N1—C10—H10A109.5C14—C19—N2124.72 (13)
C6—C1—C2—C30.4 (2)C14—N1—C10—C11−116.19 (14)
C7—C1—C2—C3−177.05 (15)C12—O3—C11—O2−1.0 (2)
C1—C2—C3—C4−1.3 (3)C12—O3—C11—C10−179.08 (14)
C2—C3—C4—C51.0 (3)N1—C10—C11—O220.5 (2)
C3—C4—C5—C60.2 (3)N1—C10—C11—O3−161.39 (13)
C4—C5—C6—C1−1.1 (3)C11—O3—C12—C13−169.68 (13)
C2—C1—C6—C50.9 (2)C9—N1—C14—C15135.77 (15)
C7—C1—C6—C5178.28 (15)C10—N1—C14—C15−43.45 (18)
C19—N2—C7—C1−175.16 (12)C9—N1—C14—C19−46.5 (2)
C19—N2—C7—C82.8 (2)C10—N1—C14—C19134.31 (15)
C6—C1—C7—N2−26.6 (2)C19—C14—C15—C161.0 (2)
C2—C1—C7—N2150.72 (15)N1—C14—C15—C16178.85 (13)
C6—C1—C7—C8155.40 (14)C14—C15—C16—C17−0.2 (2)
C2—C1—C7—C8−27.3 (2)C15—C16—C17—C18−0.8 (3)
N2—C7—C8—C9−74.71 (17)C16—C17—C18—C191.2 (3)
C1—C7—C8—C9103.20 (15)C17—C18—C19—C14−0.4 (2)
C14—N1—C9—O1−176.16 (13)C17—C18—C19—N2−176.23 (14)
C10—N1—C9—O13.1 (2)C15—C14—C19—C18−0.7 (2)
C14—N1—C9—C87.5 (2)N1—C14—C19—C18−178.44 (13)
C10—N1—C9—C8−173.24 (12)C15—C14—C19—N2174.79 (14)
C7—C8—C9—O1−111.25 (16)N1—C14—C19—N2−2.9 (2)
C7—C8—C9—N165.00 (16)C7—N2—C19—C18−140.71 (15)
C9—N1—C10—C1164.53 (18)C7—N2—C19—C1443.7 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2051).

References

  • Ahabchane, N. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519–523.
  • Ballo, D., Ahabchane, N. H., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1277. [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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