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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 July 2010; accepted 15 July 2010; online 21 July 2010)

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[Ahabchane, N. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519-523.]). For a related structure, see: Ballo et al. (2010[Ballo, D., Ahabchane, N. H., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1277.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19N3O3

  • Mr = 349.38

  • Orthorhombic, P 21 21 21

  • 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)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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)°].

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C20H19N3O3 at the 50% probability level.
1-[2-(2-Oxo-1,3-oxazolidin-3-yl)ethyl]-4-phenyl-1H- 1,5-benzodiazepin-2(3H)-one top
Crystal data top
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 top
Bruker X8 APEXII
diffractometer
1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 26.7°, θmin = 2.9°
ϕ and ω scansh = 1110
9253 measured reflectionsk = 1413
2053 independent reflectionsl = 2014
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.90 w = 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
Crystal data top
C20H19N3O3V = 1704.34 (15) Å3
Mr = 349.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.0163 (5) ŵ = 0.09 mm1
b = 11.6671 (6) ÅT = 293 K
c = 16.2019 (8) Å0.25 × 0.25 × 0.15 mm
Data collection top
Bruker X8 APEXII
diffractometer
1578 reflections with I > 2σ(I)
9253 measured reflectionsRint = 0.039
2053 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.90Δρmax = 0.12 e Å3
2053 reflectionsΔρmin = 0.16 e Å3
235 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
C40.0596 (3)0.6950 (3)0.29269 (17)0.0646 (8)
H40.15940.71100.28410.078*
C50.0192 (3)0.5927 (2)0.32647 (15)0.0520 (6)
H50.09210.54030.34140.062*
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) top
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, º) top
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—C2132.7 (2)C9—N1—C10—C11108.0 (2)
C10—N1—C1—C252.3 (3)C1—N1—C10—C1167.3 (3)
C9—N1—C1—C649.8 (3)C12—N3—C11—C10137.1 (2)
C10—N1—C1—C6125.2 (2)C13—N3—C11—C1066.2 (3)
C6—C1—C2—C30.7 (4)N1—C10—C11—N357.5 (3)
N1—C1—C2—C3176.8 (3)C14—O3—C12—O2176.3 (3)
C1—C2—C3—C40.7 (5)C14—O3—C12—N34.3 (3)
C2—C3—C4—C50.6 (4)C11—N3—C12—O212.8 (4)
C3—C4—C5—C61.0 (4)C13—N3—C12—O2172.0 (3)
C2—C1—C6—C52.2 (3)C11—N3—C12—O3166.5 (2)
N1—C1—C6—C5175.2 (2)C13—N3—C12—O37.3 (3)
C2—C1—C6—N2179.1 (2)C12—N3—C13—C1414.8 (3)
N1—C1—C6—N21.6 (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—O316.4 (3)
C7—N2—C6—C142.9 (3)N2—C7—C15—C20161.8 (2)
C7—N2—C6—C5140.2 (2)C8—C7—C15—C2022.5 (3)
C6—N2—C7—C15173.44 (19)N2—C7—C15—C1619.4 (3)
C6—N2—C7—C82.2 (3)C8—C7—C15—C16156.3 (2)
N2—C7—C8—C976.5 (3)C20—C15—C16—C170.4 (4)
C15—C7—C8—C999.1 (2)C7—C15—C16—C17178.4 (2)
C1—N1—C9—O1178.2 (2)C15—C16—C17—C180.2 (4)
C10—N1—C9—O16.8 (3)C16—C17—C18—C191.3 (4)
C1—N1—C9—C85.5 (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—N168.8 (2)C18—C19—C20—C151.2 (5)

Experimental details

Crystal data
Chemical formulaC20H19N3O3
Mr349.38
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)9.0163 (5), 11.6671 (6), 16.2019 (8)
V3)1704.34 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.25 × 0.15
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9253, 2053, 1578
Rint0.039
(sin θ/λ)max1)0.631
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 0.90
No. of reflections2053
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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

References

First citationAhabchane, N. H., Keita, A. & Essassi, E. M. (1999). C. R. Ser. IIC, 2, 519–523.  CAS
First citationBallo, D., Ahabchane, N. H., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1277.  Web of Science CSD CrossRef IUCr Journals
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds