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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2080.
Published online 2010 July 21. doi:  10.1107/S160053681002828X
PMCID: PMC3007442

1-[2-(2-Oxo-1,3-oxazolidin-3-yl)eth­yl]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

Abstract

The seven-membered ring in the title compound, C20H19N3O3, 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 = 0.358 Å) and the phenyl substituent is 55.8 (1)°. The two rings at either ends of the ethyl chain are staggered [N—CH2—CH2—N torsion angle = 57.5 (4)°].

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]).

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Object name is e-66-o2080-scheme1.jpg

Experimental

Crystal data

  • C20H19N3O3
  • M r = 349.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2080-efi1.jpg
  • a = 9.0163 (5) Å
  • b = 11.6671 (6) Å
  • c = 16.2019 (8) Å
  • V = 1704.34 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.25 × 0.25 × 0.15 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 9253 measured reflections
  • 2053 independent reflections
  • 1578 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.102
  • S = 0.90
  • 2053 reflections
  • 235 parameters
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.16 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/S160053681002828X/zs2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002828X/zs2052Isup2.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 presented 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 oxazolidin-2-onyl-ethyl 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 and adopts a boat-shaped conformation, two phenylene carbons representing the stern and the methylene carbon atom the prow [r.m.s deviation 0.358 Å]. The methyl carbon deviates by 0.637 Å from the best plane. The two rings at either end of the ethyl chain are staggered [N–CH2–CH2–N torsion angle, 57.5 (4)°].

Experimental

To a solution of 4-phenyl-1H-1,5-benzodiazepin-2-one (2 g, 8,.4 mmol) in DMF (40 ml) was added dichloroethylamine hydrochloride (0.9 g, 8.4 mmol), potassium carbonate (3 g, 22.2 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The mixture was heated on a sand bath, the reaction monotired by thin layer chromatography. On completion of the reaction, the solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to afford the title compound as colorless 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 Uiso(H) set to 1.2–1.5Ueq(C). 1486 Friedel pairs were merged in the final cycles of the refinement.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the molecule of C20H19N3O3 at the 50% probability level.

Crystal data

C20H19N3O3F(000) = 736
Mr = 349.38Dx = 1.362 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2227 reflections
a = 9.0163 (5) Åθ = 2.9–21.0°
b = 11.6671 (6) ŵ = 0.09 mm1
c = 16.2019 (8) ÅT = 293 K
V = 1704.34 (15) Å3Prism, colorless
Z = 40.25 × 0.25 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 26.7°, θmin = 2.9°
[var phi] and ω scansh = −11→10
9253 measured reflectionsk = −14→13
2053 independent reflectionsl = −20→14

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.0742P)2] where P = (Fo2 + 2Fc2)/3
2053 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = −0.16 e Å3

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

xyzUiso*/Ueq
N10.3905 (2)0.62919 (16)0.33575 (12)0.0439 (5)
N20.1611 (2)0.45822 (16)0.37488 (12)0.0416 (5)
N30.4287 (2)0.61202 (17)0.51545 (12)0.0458 (5)
O10.5951 (2)0.51620 (17)0.32572 (12)0.0669 (5)
O20.1947 (2)0.60716 (17)0.57036 (13)0.0677 (6)
O30.3700 (2)0.48444 (16)0.61065 (11)0.0629 (5)
C10.2372 (3)0.6471 (2)0.31906 (14)0.0434 (5)
C20.1935 (3)0.7508 (2)0.28491 (17)0.0597 (7)
H20.26500.80490.27100.072*
C30.0461 (4)0.7750 (2)0.27117 (19)0.0697 (8)
H30.01810.84450.24770.084*
C4−0.0596 (3)0.6950 (3)0.29269 (17)0.0646 (8)
H4−0.15940.71100.28410.078*
C5−0.0192 (3)0.5927 (2)0.32647 (15)0.0520 (6)
H5−0.09210.54030.34140.062*
C60.1301 (3)0.5651 (2)0.33911 (13)0.0416 (5)
C70.2709 (3)0.39924 (19)0.34851 (13)0.0405 (5)
C80.3658 (3)0.4400 (2)0.27737 (14)0.0477 (6)
H8A0.42480.37750.25540.057*
H8B0.30460.47100.23350.057*
C90.4635 (3)0.5312 (2)0.31346 (14)0.0467 (6)
C100.4696 (3)0.7153 (2)0.38443 (15)0.0516 (6)
H10A0.45600.78990.35920.062*
H10B0.57480.69790.38390.062*
C110.4161 (3)0.7200 (2)0.47313 (15)0.0483 (6)
H11A0.47320.77720.50270.058*
H11B0.31310.74400.47370.058*
C120.3193 (3)0.5726 (2)0.56469 (15)0.0480 (6)
C130.5683 (3)0.5585 (3)0.53446 (17)0.0590 (7)
H13A0.63270.60960.56520.071*
H13B0.61900.53330.48490.071*
C140.5192 (4)0.4584 (3)0.58632 (19)0.0697 (8)
H14A0.52240.38790.55460.084*
H14B0.58260.45000.63430.084*
C150.3119 (3)0.29286 (18)0.39276 (14)0.0415 (5)
C160.2634 (3)0.2771 (2)0.47373 (17)0.0542 (6)
H160.20400.33210.49890.065*
C170.3038 (4)0.1793 (3)0.51664 (19)0.0674 (8)
H170.27100.16900.57060.081*
C180.3914 (3)0.0977 (3)0.4807 (2)0.0658 (8)
H180.41950.03310.51040.079*
C190.4373 (4)0.1114 (3)0.4010 (2)0.0701 (8)
H190.49460.05510.37590.084*
C200.3988 (3)0.2088 (2)0.35785 (18)0.0604 (7)
H200.43230.21800.30400.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0423 (11)0.0491 (11)0.0402 (10)−0.0064 (9)−0.0003 (9)0.0029 (9)
N20.0395 (11)0.0438 (10)0.0415 (10)−0.0009 (9)−0.0001 (8)−0.0040 (9)
N30.0414 (11)0.0531 (11)0.0428 (11)0.0005 (9)0.0037 (9)0.0065 (9)
O10.0407 (10)0.0837 (13)0.0761 (13)0.0036 (10)0.0055 (9)0.0061 (12)
O20.0511 (11)0.0706 (12)0.0815 (13)0.0082 (11)0.0214 (10)0.0049 (10)
O30.0706 (12)0.0607 (11)0.0575 (11)0.0065 (10)0.0181 (10)0.0150 (9)
C10.0470 (13)0.0482 (13)0.0351 (12)0.0017 (11)−0.0029 (11)−0.0027 (11)
C20.0711 (18)0.0510 (14)0.0570 (16)0.0016 (14)−0.0068 (15)0.0076 (12)
C30.080 (2)0.0593 (16)0.0695 (19)0.0250 (16)−0.0144 (17)0.0092 (15)
C40.0580 (17)0.0736 (18)0.0623 (17)0.0226 (16)−0.0112 (15)−0.0051 (15)
C50.0434 (13)0.0644 (16)0.0483 (14)0.0065 (12)−0.0018 (11)−0.0093 (13)
C60.0447 (12)0.0465 (13)0.0335 (11)0.0032 (10)−0.0008 (10)−0.0061 (10)
C70.0412 (13)0.0444 (11)0.0358 (11)−0.0024 (10)−0.0031 (10)−0.0058 (10)
C80.0558 (14)0.0542 (13)0.0330 (11)0.0057 (12)0.0038 (11)−0.0049 (11)
C90.0436 (14)0.0599 (14)0.0367 (12)0.0005 (12)0.0069 (11)0.0080 (11)
C100.0551 (14)0.0547 (13)0.0451 (13)−0.0174 (12)−0.0012 (12)0.0062 (11)
C110.0559 (15)0.0455 (13)0.0435 (13)−0.0049 (11)0.0009 (12)0.0003 (10)
C120.0544 (15)0.0460 (13)0.0434 (13)0.0008 (12)0.0077 (11)−0.0045 (11)
C130.0464 (14)0.0794 (19)0.0513 (15)0.0070 (13)0.0019 (12)0.0094 (14)
C140.0655 (18)0.0788 (19)0.0650 (17)0.0178 (16)0.0061 (15)0.0164 (16)
C150.0388 (11)0.0417 (11)0.0440 (13)−0.0032 (10)−0.0055 (10)−0.0049 (10)
C160.0557 (15)0.0557 (14)0.0512 (15)−0.0024 (12)−0.0012 (13)0.0025 (13)
C170.0756 (19)0.0734 (18)0.0532 (16)−0.0086 (17)−0.0077 (15)0.0144 (15)
C180.0613 (17)0.0592 (17)0.077 (2)0.0008 (14)−0.0237 (16)0.0153 (15)
C190.074 (2)0.0600 (17)0.077 (2)0.0218 (15)−0.0054 (17)−0.0025 (15)
C200.0643 (18)0.0614 (16)0.0554 (16)0.0138 (14)−0.0014 (14)−0.0048 (13)

Geometric parameters (Å, °)

N1—C91.367 (3)C8—C91.501 (3)
N1—C11.424 (3)C8—H8A0.9700
N1—C101.463 (3)C8—H8B0.9700
N2—C71.280 (3)C10—C111.517 (4)
N2—C61.403 (3)C10—H10A0.9700
N3—C121.350 (3)C10—H10B0.9700
N3—C111.439 (3)C11—H11A0.9700
N3—C131.439 (3)C11—H11B0.9700
O1—C91.216 (3)C13—C141.505 (4)
O2—C121.197 (3)C13—H13A0.9700
O3—C121.350 (3)C13—H13B0.9700
O3—C141.435 (4)C14—H14A0.9700
C1—C21.387 (3)C14—H14B0.9700
C1—C61.398 (3)C15—C201.377 (3)
C2—C31.377 (4)C15—C161.395 (4)
C2—H20.9300C16—C171.385 (4)
C3—C41.378 (4)C16—H160.9300
C3—H30.9300C17—C181.367 (4)
C4—C51.363 (4)C17—H170.9300
C4—H40.9300C18—C191.364 (5)
C5—C61.399 (3)C18—H180.9300
C5—H50.9300C19—C201.379 (4)
C7—C151.480 (3)C19—H190.9300
C7—C81.512 (3)C20—H200.9300
C9—N1—C1122.7 (2)C11—C10—H10B109.1
C9—N1—C10118.8 (2)H10A—C10—H10B107.9
C1—N1—C10118.3 (2)N3—C11—C10113.2 (2)
C7—N2—C6119.6 (2)N3—C11—H11A108.9
C12—N3—C11121.5 (2)C10—C11—H11A108.9
C12—N3—C13111.40 (19)N3—C11—H11B108.9
C11—N3—C13123.5 (2)C10—C11—H11B108.9
C12—O3—C14109.1 (2)H11A—C11—H11B107.7
C2—C1—C6119.6 (2)O2—C12—O3122.2 (2)
C2—C1—N1118.7 (2)O2—C12—N3128.1 (2)
C6—C1—N1121.7 (2)O3—C12—N3109.8 (2)
C3—C2—C1121.2 (3)N3—C13—C14101.5 (2)
C3—C2—H2119.4N3—C13—H13A111.5
C1—C2—H2119.4C14—C13—H13A111.5
C2—C3—C4119.1 (3)N3—C13—H13B111.5
C2—C3—H3120.4C14—C13—H13B111.5
C4—C3—H3120.4H13A—C13—H13B109.3
C5—C4—C3120.7 (3)O3—C14—C13105.4 (2)
C5—C4—H4119.7O3—C14—H14A110.7
C3—C4—H4119.7C13—C14—H14A110.7
C4—C5—C6121.1 (3)O3—C14—H14B110.7
C4—C5—H5119.4C13—C14—H14B110.7
C6—C5—H5119.4H14A—C14—H14B108.8
C1—C6—C5118.3 (2)C20—C15—C16118.1 (2)
C1—C6—N2124.5 (2)C20—C15—C7122.7 (2)
C5—C6—N2117.2 (2)C16—C15—C7119.2 (2)
N2—C7—C15118.8 (2)C17—C16—C15119.9 (3)
N2—C7—C8121.6 (2)C17—C16—H16120.0
C15—C7—C8119.5 (2)C15—C16—H16120.0
C9—C8—C7104.95 (17)C18—C17—C16120.7 (3)
C9—C8—H8A110.8C18—C17—H17119.6
C7—C8—H8A110.8C16—C17—H17119.6
C9—C8—H8B110.8C19—C18—C17119.8 (3)
C7—C8—H8B110.8C19—C18—H18120.1
H8A—C8—H8B108.8C17—C18—H18120.1
O1—C9—N1123.2 (2)C18—C19—C20120.0 (3)
O1—C9—C8122.3 (2)C18—C19—H19120.0
N1—C9—C8114.4 (2)C20—C19—H19120.0
N1—C10—C11112.4 (2)C15—C20—C19121.4 (3)
N1—C10—H10A109.1C15—C20—H20119.3
C11—C10—H10A109.1C19—C20—H20119.3
N1—C10—H10B109.1
C9—N1—C1—C2−132.7 (2)C9—N1—C10—C11−108.0 (2)
C10—N1—C1—C252.3 (3)C1—N1—C10—C1167.3 (3)
C9—N1—C1—C649.8 (3)C12—N3—C11—C10−137.1 (2)
C10—N1—C1—C6−125.2 (2)C13—N3—C11—C1066.2 (3)
C6—C1—C2—C30.7 (4)N1—C10—C11—N357.5 (3)
N1—C1—C2—C3−176.8 (3)C14—O3—C12—O2176.3 (3)
C1—C2—C3—C40.7 (5)C14—O3—C12—N3−4.3 (3)
C2—C3—C4—C5−0.6 (4)C11—N3—C12—O212.8 (4)
C3—C4—C5—C6−1.0 (4)C13—N3—C12—O2172.0 (3)
C2—C1—C6—C5−2.2 (3)C11—N3—C12—O3−166.5 (2)
N1—C1—C6—C5175.2 (2)C13—N3—C12—O3−7.3 (3)
C2—C1—C6—N2−179.1 (2)C12—N3—C13—C1414.8 (3)
N1—C1—C6—N2−1.6 (3)C11—N3—C13—C14173.5 (2)
C4—C5—C6—C12.4 (4)C12—O3—C14—C1313.4 (3)
C4—C5—C6—N2179.5 (2)N3—C13—C14—O3−16.4 (3)
C7—N2—C6—C1−42.9 (3)N2—C7—C15—C20161.8 (2)
C7—N2—C6—C5140.2 (2)C8—C7—C15—C20−22.5 (3)
C6—N2—C7—C15173.44 (19)N2—C7—C15—C16−19.4 (3)
C6—N2—C7—C8−2.2 (3)C8—C7—C15—C16156.3 (2)
N2—C7—C8—C976.5 (3)C20—C15—C16—C170.4 (4)
C15—C7—C8—C9−99.1 (2)C7—C15—C16—C17−178.4 (2)
C1—N1—C9—O1178.2 (2)C15—C16—C17—C180.2 (4)
C10—N1—C9—O1−6.8 (3)C16—C17—C18—C19−1.3 (4)
C1—N1—C9—C8−5.5 (3)C17—C18—C19—C201.8 (5)
C10—N1—C9—C8169.45 (19)C16—C15—C20—C190.1 (4)
C7—C8—C9—O1107.4 (3)C7—C15—C20—C19178.9 (3)
C7—C8—C9—N1−68.8 (2)C18—C19—C20—C15−1.2 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2052).

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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