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

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ISSN: 2056-9890

5-Acetyl-3-hy­dr­oxy-4-phenyl-4,5-di­hydro-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, bInstitute of Nanomaterials and Nanotechnology MAScIR, Avenue de l'Armée Royale, Rabat, Morocco, cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 November 2011; accepted 10 November 2011; online 16 November 2011)

In the title compound, C17H16N2O3, the seven-membered diazepine ring adopts a boat conformation with the hy­droxy-substituted C atom at the prow and fused benzene ring C atoms at the stern. The phenyl substituent occupies an equatorial position. The amino group of the ring system is a hydrogen-bond donor to the oxo O atom of an inversion-related mol­ecule, and the hy­droxy group is a hydrogen-bond donor to the acetyl O atom of another inversion-related mol­ecule. The two hydrogen bonds generate a ribbon motif parallel to [10[\overline{1}]] in the crystal structure.

Related literature

For a related 1,5-benzodiazepin-2(3H)-one structure, see: Rida et al. (2011[Rida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945-o946.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16N2O3

  • Mr = 296.32

  • Triclinic, [P \overline 1]

  • a = 8.9710 (1) Å

  • b = 9.3142 (1) Å

  • c = 9.4129 (1) Å

  • α = 81.563 (1)°

  • β = 68.921 (1)°

  • γ = 80.146 (1)°

  • V = 719.95 (1) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.29 × 0.23 × 0.18 mm

Data collection
  • Bruker APEX DUO diffractometer

  • 19110 measured reflections

  • 4203 independent reflections

  • 3584 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.149

  • S = 1.02

  • 4203 reflections

  • 208 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.89 (2) 2.04 (2) 2.924 (1) 175 (2)
O2—H2⋯O3ii 0.83 (2) 2.09 (2) 2.905 (1) 168 (2)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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 report on 3-hydroxy-4-phenyl-1-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one provides the preparation and biological activity of this class of benzodiazepin-2-ones (Rida et al., 2011). In the present study, the reactant, 3-ydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one, has two amino –NH– units in the ring system; however, only one site is acetylated when the compound is treated with acetic anhydride. In the title compound, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern; the phenyl substituent occupies an equatorial position (Fig. 1). The amino group of the ring system is a hydrogen-bond donor to the oxo O atom of an inversion-related molecule, and the hydroxy group is hydrogen-bond donor to the acetyl O atom of another inversion-related molecule (Table 1). The two hydrogen bonds generate a ribbon motif parallel to [1 0 - 1] (Fig. 2).

Related literature top

For a related 1,5-benzodiazepin-2(3H)-one structure, see: Rida et al. (2011).

Experimental top

3-Hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one (1 g. 3.9 mmol) was heated in acetic anhydride (20 ml) for 12 h. The precipitate was collected and recrystallized from ethanol to afford colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The amino and hydroxy H-atoms were located in a difference Fourier map and were freely refined.

Structure description top

The report on 3-hydroxy-4-phenyl-1-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one provides the preparation and biological activity of this class of benzodiazepin-2-ones (Rida et al., 2011). In the present study, the reactant, 3-ydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one, has two amino –NH– units in the ring system; however, only one site is acetylated when the compound is treated with acetic anhydride. In the title compound, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern; the phenyl substituent occupies an equatorial position (Fig. 1). The amino group of the ring system is a hydrogen-bond donor to the oxo O atom of an inversion-related molecule, and the hydroxy group is hydrogen-bond donor to the acetyl O atom of another inversion-related molecule (Table 1). The two hydrogen bonds generate a ribbon motif parallel to [1 0 - 1] (Fig. 2).

For a related 1,5-benzodiazepin-2(3H)-one structure, see: Rida et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 C17H16N2O3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Ribbon motif.
5-Acetyl-3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin- 2(3H)-one top
Crystal data top
C17H16N2O3Z = 2
Mr = 296.32F(000) = 312
Triclinic, P1Dx = 1.367 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9710 (1) ÅCell parameters from 9950 reflections
b = 9.3142 (1) Åθ = 2.2–34.5°
c = 9.4129 (1) ŵ = 0.10 mm1
α = 81.563 (1)°T = 293 K
β = 68.921 (1)°Prism, colorless
γ = 80.146 (1)°0.29 × 0.23 × 0.18 mm
V = 719.95 (1) Å3
Data collection top
Bruker APEX DUO
diffractometer
3584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 30.0°, θmin = 2.2°
ω scansh = 1212
19110 measured reflectionsk = 1313
4203 independent reflectionsl = 1313
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0876P)2 + 0.1414P]
where P = (Fo2 + 2Fc2)/3
4203 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C17H16N2O3γ = 80.146 (1)°
Mr = 296.32V = 719.95 (1) Å3
Triclinic, P1Z = 2
a = 8.9710 (1) ÅMo Kα radiation
b = 9.3142 (1) ŵ = 0.10 mm1
c = 9.4129 (1) ÅT = 293 K
α = 81.563 (1)°0.29 × 0.23 × 0.18 mm
β = 68.921 (1)°
Data collection top
Bruker APEX DUO
diffractometer
3584 reflections with I > 2σ(I)
19110 measured reflectionsRint = 0.024
4203 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.30 e Å3
4203 reflectionsΔρmin = 0.27 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.18813 (12)0.41278 (9)0.39332 (11)0.0488 (2)
O20.50968 (12)0.39185 (9)0.34285 (10)0.0430 (2)
O30.41433 (13)0.74792 (11)0.06449 (10)0.0513 (2)
N10.14350 (13)0.64817 (10)0.44597 (12)0.0426 (2)
N20.37829 (11)0.75893 (9)0.18338 (9)0.03178 (19)
C10.19921 (15)0.78134 (12)0.44620 (13)0.0406 (3)
C20.1358 (2)0.85962 (16)0.57413 (16)0.0656 (5)
H2A0.05470.82530.65990.079*
C30.1927 (3)0.98823 (18)0.5745 (2)0.0756 (6)
H30.14991.03960.66090.091*
C40.3123 (2)1.04144 (16)0.4483 (2)0.0639 (4)
H40.35011.12800.44960.077*
C50.37548 (17)0.96508 (13)0.31996 (15)0.0468 (3)
H50.45700.99990.23490.056*
C60.31790 (13)0.83653 (11)0.31723 (12)0.0346 (2)
C70.24114 (14)0.52550 (11)0.39399 (12)0.0363 (2)
C80.42230 (13)0.53221 (11)0.34285 (11)0.0329 (2)
H80.44070.58430.41710.039*
C90.48415 (12)0.61900 (10)0.18549 (10)0.0293 (2)
H90.47580.56170.10990.035*
C100.65889 (13)0.64317 (11)0.13784 (12)0.0345 (2)
C110.72509 (17)0.67606 (14)0.24003 (18)0.0493 (3)
H110.66250.68250.34250.059*
C120.8864 (2)0.69927 (17)0.1874 (3)0.0685 (5)
H120.93110.72120.25550.082*
C130.98046 (18)0.69010 (16)0.0359 (3)0.0722 (6)
H131.08760.70660.00200.087*
C140.91519 (18)0.65653 (16)0.0649 (2)0.0624 (4)
H140.97860.64930.16710.075*
C150.75549 (15)0.63361 (13)0.01454 (15)0.0450 (3)
H150.71200.61150.08350.054*
C160.35154 (14)0.81314 (12)0.05077 (12)0.0371 (2)
C170.24042 (18)0.95367 (15)0.05114 (17)0.0529 (3)
H17A0.19830.95970.03030.079*
H17B0.29881.03500.03670.079*
H17C0.15320.95600.14720.079*
H10.042 (2)0.635 (2)0.498 (2)0.057 (5)*
H20.517 (2)0.353 (2)0.266 (2)0.065 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0575 (5)0.0342 (4)0.0491 (5)0.0188 (4)0.0046 (4)0.0074 (3)
O20.0622 (5)0.0290 (4)0.0370 (4)0.0006 (3)0.0196 (4)0.0017 (3)
O30.0650 (6)0.0559 (6)0.0302 (4)0.0024 (4)0.0175 (4)0.0038 (4)
N10.0456 (5)0.0311 (5)0.0406 (5)0.0124 (4)0.0015 (4)0.0043 (4)
N20.0399 (4)0.0259 (4)0.0254 (4)0.0040 (3)0.0067 (3)0.0015 (3)
C10.0511 (6)0.0282 (5)0.0330 (5)0.0082 (4)0.0009 (4)0.0050 (4)
C20.0924 (12)0.0422 (7)0.0385 (6)0.0147 (7)0.0118 (7)0.0120 (5)
C30.1156 (15)0.0465 (8)0.0507 (8)0.0142 (9)0.0023 (9)0.0248 (6)
C40.0897 (11)0.0368 (6)0.0631 (9)0.0180 (7)0.0139 (8)0.0185 (6)
C50.0571 (7)0.0316 (5)0.0465 (6)0.0148 (5)0.0066 (5)0.0058 (4)
C60.0432 (5)0.0258 (4)0.0298 (5)0.0061 (4)0.0052 (4)0.0040 (3)
C70.0491 (6)0.0288 (5)0.0270 (4)0.0114 (4)0.0062 (4)0.0004 (3)
C80.0469 (5)0.0254 (4)0.0259 (4)0.0063 (4)0.0116 (4)0.0009 (3)
C90.0385 (5)0.0249 (4)0.0240 (4)0.0057 (3)0.0091 (3)0.0028 (3)
C100.0389 (5)0.0254 (4)0.0381 (5)0.0054 (4)0.0111 (4)0.0034 (4)
C110.0556 (7)0.0410 (6)0.0608 (8)0.0076 (5)0.0281 (6)0.0112 (5)
C120.0610 (9)0.0441 (7)0.1198 (16)0.0066 (6)0.0511 (10)0.0159 (8)
C130.0406 (7)0.0385 (7)0.1285 (17)0.0077 (5)0.0178 (9)0.0063 (8)
C140.0456 (7)0.0411 (7)0.0778 (10)0.0069 (5)0.0034 (7)0.0027 (6)
C150.0454 (6)0.0376 (6)0.0426 (6)0.0069 (5)0.0042 (5)0.0013 (4)
C160.0414 (5)0.0350 (5)0.0313 (5)0.0071 (4)0.0097 (4)0.0036 (4)
C170.0566 (7)0.0426 (6)0.0510 (7)0.0028 (5)0.0171 (6)0.0076 (5)
Geometric parameters (Å, º) top
O1—C71.2261 (13)C7—C81.5297 (16)
O2—C81.4046 (13)C8—C91.5382 (13)
O2—H20.83 (2)C8—H80.9800
O3—C161.2247 (14)C9—C101.5148 (14)
N1—C71.3510 (15)C9—H90.9800
N1—C11.4149 (14)C10—C111.3897 (17)
N1—H10.89 (2)C10—C151.3905 (16)
N2—C161.3637 (14)C11—C121.395 (2)
N2—C61.4302 (13)C11—H110.9300
N2—C91.4776 (12)C12—C131.378 (3)
C1—C21.3886 (17)C12—H120.9300
C1—C61.3950 (15)C13—C141.375 (3)
C2—C31.381 (2)C13—H130.9300
C2—H2A0.9300C14—C151.3818 (19)
C3—C41.378 (3)C14—H140.9300
C3—H30.9300C15—H150.9300
C4—C51.3814 (19)C16—C171.5031 (17)
C4—H40.9300C17—H17A0.9600
C5—C61.3897 (15)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C8—O2—H2109.8 (14)N2—C9—C10111.43 (8)
C7—N1—C1124.00 (10)N2—C9—C8109.66 (8)
C7—N1—H1114.4 (12)C10—C9—C8113.46 (9)
C1—N1—H1120.4 (12)N2—C9—H9107.3
C16—N2—C6122.88 (9)C10—C9—H9107.3
C16—N2—C9118.55 (8)C8—C9—H9107.3
C6—N2—C9118.41 (8)C11—C10—C15119.09 (12)
C2—C1—C6119.01 (11)C11—C10—C9122.52 (10)
C2—C1—N1120.58 (11)C15—C10—C9118.38 (10)
C6—C1—N1120.40 (10)C10—C11—C12119.33 (15)
C3—C2—C1120.25 (13)C10—C11—H11120.3
C3—C2—H2A119.9C12—C11—H11120.3
C1—C2—H2A119.9C13—C12—C11120.92 (16)
C4—C3—C2120.84 (13)C13—C12—H12119.5
C4—C3—H3119.6C11—C12—H12119.5
C2—C3—H3119.6C14—C13—C12119.71 (14)
C3—C4—C5119.44 (13)C14—C13—H13120.1
C3—C4—H4120.3C12—C13—H13120.1
C5—C4—H4120.3C13—C14—C15120.03 (16)
C4—C5—C6120.37 (12)C13—C14—H14120.0
C4—C5—H5119.8C15—C14—H14120.0
C6—C5—H5119.8C14—C15—C10120.91 (14)
C5—C6—C1120.05 (10)C14—C15—H15119.5
C5—C6—N2121.01 (10)C10—C15—H15119.5
C1—C6—N2118.94 (9)O3—C16—N2120.90 (10)
O1—C7—N1122.08 (11)O3—C16—C17121.05 (11)
O1—C7—C8121.49 (10)N2—C16—C17118.04 (10)
N1—C7—C8116.36 (9)C16—C17—H17A109.5
O2—C8—C7111.68 (8)C16—C17—H17B109.5
O2—C8—C9110.91 (8)H17A—C17—H17B109.5
C7—C8—C9111.53 (9)C16—C17—H17C109.5
O2—C8—H8107.5H17A—C17—H17C109.5
C7—C8—H8107.5H17B—C17—H17C109.5
C9—C8—H8107.5
C7—N1—C1—C2134.65 (15)C6—N2—C9—C1087.10 (10)
C7—N1—C1—C645.87 (19)C16—N2—C9—C8145.05 (10)
C6—C1—C2—C31.6 (3)C6—N2—C9—C839.37 (12)
N1—C1—C2—C3178.87 (17)O2—C8—C9—N2173.40 (8)
C1—C2—C3—C40.3 (3)C7—C8—C9—N248.24 (11)
C2—C3—C4—C50.1 (3)O2—C8—C9—C1061.29 (11)
C3—C4—C5—C60.7 (3)C7—C8—C9—C10173.56 (8)
C4—C5—C6—C12.0 (2)N2—C9—C10—C1184.57 (12)
C4—C5—C6—N2177.86 (14)C8—C9—C10—C1139.79 (14)
C2—C1—C6—C52.5 (2)N2—C9—C10—C1594.64 (11)
N1—C1—C6—C5178.04 (12)C8—C9—C10—C15140.99 (10)
C2—C1—C6—N2177.42 (13)C15—C10—C11—C120.26 (18)
N1—C1—C6—N22.06 (18)C9—C10—C11—C12178.95 (11)
C16—N2—C6—C567.48 (16)C10—C11—C12—C130.0 (2)
C9—N2—C6—C5107.89 (12)C11—C12—C13—C140.5 (2)
C16—N2—C6—C1112.42 (13)C12—C13—C14—C150.7 (2)
C9—N2—C6—C172.21 (14)C13—C14—C15—C100.4 (2)
C1—N1—C7—O1178.75 (11)C11—C10—C15—C140.10 (18)
C1—N1—C7—C84.08 (17)C9—C10—C15—C14179.14 (11)
O1—C7—C8—O218.12 (14)C6—N2—C16—O3175.01 (10)
N1—C7—C8—O2159.07 (10)C9—N2—C16—O30.35 (16)
O1—C7—C8—C9106.61 (11)C6—N2—C16—C176.10 (16)
N1—C7—C8—C976.20 (12)C9—N2—C16—C17178.53 (10)
C16—N2—C9—C1088.48 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.89 (2)2.04 (2)2.924 (1)175 (2)
O2—H2···O3ii0.83 (2)2.09 (2)2.905 (1)168 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H16N2O3
Mr296.32
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.9710 (1), 9.3142 (1), 9.4129 (1)
α, β, γ (°)81.563 (1), 68.921 (1), 80.146 (1)
V3)719.95 (1)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.29 × 0.23 × 0.18
Data collection
DiffractometerBruker APEX DUO
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19110, 4203, 3584
Rint0.024
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.149, 1.02
No. of reflections4203
No. of parameters208
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.89 (2)2.04 (2)2.924 (1)175 (2)
O2—H2···O3ii0.83 (2)2.09 (2)2.905 (1)168 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.
 

Acknowledgements

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

References

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First citationRida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945–o946.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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