5-Acetyl-3-hy­droxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one

Rida, M.; Alsubari, A.; Essassi, E.M.; Zouihri, H.; Ng, S.W.

doi:10.1107/S1600536811047878

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3337

https://doi.org/10.1107/S1600536811047878

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5-Acetyl-3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one

Mohamed Rida,^a Abdusalam Alsubari,^a El Mokhtar Essassi,^a Hafid Zouihri ^b and Seik Weng Ng ^c,^d ^*

^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 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₃
M_r = 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)
R_int = 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
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811047878/lh5376sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047878/lh5376Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047878/lh5376Isup3.cml

checkCIF report

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.

Structure description top

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

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₇H₁₆N₂O₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Ribbon motif.

5-Acetyl-3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin- 2(3H)-one top

Crystal data top

C₁₇H₁₆N₂O₃	Z = 2
M_r = 296.32	F(000) = 312
Triclinic, P1	D_x = 1.367 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9710 (1) Å	Cell parameters from 9950 reflections
b = 9.3142 (1) Å	θ = 2.2–34.5°
c = 9.4129 (1) Å	µ = 0.10 mm⁻¹
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 tube	R_int = 0.024
Graphite monochromator	θ_max = 30.0°, θ_min = 2.2°
ω scans	h = −12→12
19110 measured reflections	k = −13→13
4203 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0876P)² + 0.1414P] where P = (F_o² + 2F_c²)/3
4203 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O₃	γ = 80.146 (1)°
M_r = 296.32	V = 719.95 (1) Å³
Triclinic, P1	Z = 2
a = 8.9710 (1) Å	Mo Kα radiation
b = 9.3142 (1) Å	µ = 0.10 mm⁻¹
c = 9.4129 (1) Å	T = 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 reflections	R_int = 0.024
4203 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
4203 reflections	Δρ_min = −0.27 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.18813 (12)	0.41278 (9)	0.39332 (11)	0.0488 (2)
O2	0.50968 (12)	0.39185 (9)	0.34285 (10)	0.0430 (2)
O3	0.41433 (13)	0.74792 (11)	−0.06449 (10)	0.0513 (2)
N1	0.14350 (13)	0.64817 (10)	0.44597 (12)	0.0426 (2)
N2	0.37829 (11)	0.75893 (9)	0.18338 (9)	0.03178 (19)
C1	0.19921 (15)	0.78134 (12)	0.44620 (13)	0.0406 (3)
C2	0.1358 (2)	0.85962 (16)	0.57413 (16)	0.0656 (5)
H2A	0.0547	0.8253	0.6599	0.079*
C3	0.1927 (3)	0.98823 (18)	0.5745 (2)	0.0756 (6)
H3	0.1499	1.0396	0.6609	0.091*
C4	0.3123 (2)	1.04144 (16)	0.4483 (2)	0.0639 (4)
H4	0.3501	1.1280	0.4496	0.077*
C5	0.37548 (17)	0.96508 (13)	0.31996 (15)	0.0468 (3)
H5	0.4570	0.9999	0.2349	0.056*
C6	0.31790 (13)	0.83653 (11)	0.31723 (12)	0.0346 (2)
C7	0.24114 (14)	0.52550 (11)	0.39399 (12)	0.0363 (2)
C8	0.42230 (13)	0.53221 (11)	0.34285 (11)	0.0329 (2)
H8	0.4407	0.5843	0.4171	0.039*
C9	0.48415 (12)	0.61900 (10)	0.18549 (10)	0.0293 (2)
H9	0.4758	0.5617	0.1099	0.035*
C10	0.65889 (13)	0.64317 (11)	0.13784 (12)	0.0345 (2)
C11	0.72509 (17)	0.67606 (14)	0.24003 (18)	0.0493 (3)
H11	0.6625	0.6825	0.3425	0.059*
C12	0.8864 (2)	0.69927 (17)	0.1874 (3)	0.0685 (5)
H12	0.9311	0.7212	0.2555	0.082*
C13	0.98046 (18)	0.69010 (16)	0.0359 (3)	0.0722 (6)
H13	1.0876	0.7066	0.0020	0.087*
C14	0.91519 (18)	0.65653 (16)	−0.0649 (2)	0.0624 (4)
H14	0.9786	0.6493	−0.1671	0.075*
C15	0.75549 (15)	0.63361 (13)	−0.01454 (15)	0.0450 (3)
H15	0.7120	0.6115	−0.0835	0.054*
C16	0.35154 (14)	0.81314 (12)	0.05077 (12)	0.0371 (2)
C17	0.24042 (18)	0.95367 (15)	0.05114 (17)	0.0529 (3)
H17A	0.1983	0.9597	−0.0303	0.079*
H17B	0.2988	1.0350	0.0367	0.079*
H17C	0.1532	0.9560	0.1472	0.079*
H1	0.042 (2)	0.635 (2)	0.498 (2)	0.057 (5)*
H2	0.517 (2)	0.353 (2)	0.266 (2)	0.065 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0575 (5)	0.0342 (4)	0.0491 (5)	−0.0188 (4)	−0.0046 (4)	−0.0074 (3)
O2	0.0622 (5)	0.0290 (4)	0.0370 (4)	0.0006 (3)	−0.0196 (4)	−0.0017 (3)
O3	0.0650 (6)	0.0559 (6)	0.0302 (4)	0.0024 (4)	−0.0175 (4)	−0.0038 (4)
N1	0.0456 (5)	0.0311 (5)	0.0406 (5)	−0.0124 (4)	0.0015 (4)	−0.0043 (4)
N2	0.0399 (4)	0.0259 (4)	0.0254 (4)	−0.0040 (3)	−0.0067 (3)	−0.0015 (3)
C1	0.0511 (6)	0.0282 (5)	0.0330 (5)	−0.0082 (4)	−0.0009 (4)	−0.0050 (4)
C2	0.0924 (12)	0.0422 (7)	0.0385 (6)	−0.0147 (7)	0.0118 (7)	−0.0120 (5)
C3	0.1156 (15)	0.0465 (8)	0.0507 (8)	−0.0142 (9)	−0.0023 (9)	−0.0248 (6)
C4	0.0897 (11)	0.0368 (6)	0.0631 (9)	−0.0180 (7)	−0.0139 (8)	−0.0185 (6)
C5	0.0571 (7)	0.0316 (5)	0.0465 (6)	−0.0148 (5)	−0.0066 (5)	−0.0058 (4)
C6	0.0432 (5)	0.0258 (4)	0.0298 (5)	−0.0061 (4)	−0.0052 (4)	−0.0040 (3)
C7	0.0491 (6)	0.0288 (5)	0.0270 (4)	−0.0114 (4)	−0.0062 (4)	−0.0004 (3)
C8	0.0469 (5)	0.0254 (4)	0.0259 (4)	−0.0063 (4)	−0.0116 (4)	−0.0009 (3)
C9	0.0385 (5)	0.0249 (4)	0.0240 (4)	−0.0057 (3)	−0.0091 (3)	−0.0028 (3)
C10	0.0389 (5)	0.0254 (4)	0.0381 (5)	−0.0054 (4)	−0.0111 (4)	−0.0034 (4)
C11	0.0556 (7)	0.0410 (6)	0.0608 (8)	−0.0076 (5)	−0.0281 (6)	−0.0112 (5)
C12	0.0610 (9)	0.0441 (7)	0.1198 (16)	−0.0066 (6)	−0.0511 (10)	−0.0159 (8)
C13	0.0406 (7)	0.0385 (7)	0.1285 (17)	−0.0077 (5)	−0.0178 (9)	−0.0063 (8)
C14	0.0456 (7)	0.0411 (7)	0.0778 (10)	−0.0069 (5)	0.0034 (7)	0.0027 (6)
C15	0.0454 (6)	0.0376 (6)	0.0426 (6)	−0.0069 (5)	−0.0042 (5)	−0.0013 (4)
C16	0.0414 (5)	0.0350 (5)	0.0313 (5)	−0.0071 (4)	−0.0097 (4)	0.0036 (4)
C17	0.0566 (7)	0.0426 (6)	0.0510 (7)	0.0028 (5)	−0.0171 (6)	0.0076 (5)

Geometric parameters (Å, º) top

O1—C7	1.2261 (13)	C7—C8	1.5297 (16)
O2—C8	1.4046 (13)	C8—C9	1.5382 (13)
O2—H2	0.83 (2)	C8—H8	0.9800
O3—C16	1.2247 (14)	C9—C10	1.5148 (14)
N1—C7	1.3510 (15)	C9—H9	0.9800
N1—C1	1.4149 (14)	C10—C11	1.3897 (17)
N1—H1	0.89 (2)	C10—C15	1.3905 (16)
N2—C16	1.3637 (14)	C11—C12	1.395 (2)
N2—C6	1.4302 (13)	C11—H11	0.9300
N2—C9	1.4776 (12)	C12—C13	1.378 (3)
C1—C2	1.3886 (17)	C12—H12	0.9300
C1—C6	1.3950 (15)	C13—C14	1.375 (3)
C2—C3	1.381 (2)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.3818 (19)
C3—C4	1.378 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3814 (19)	C16—C17	1.5031 (17)
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.3897 (15)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600

C8—O2—H2	109.8 (14)	N2—C9—C10	111.43 (8)
C7—N1—C1	124.00 (10)	N2—C9—C8	109.66 (8)
C7—N1—H1	114.4 (12)	C10—C9—C8	113.46 (9)
C1—N1—H1	120.4 (12)	N2—C9—H9	107.3
C16—N2—C6	122.88 (9)	C10—C9—H9	107.3
C16—N2—C9	118.55 (8)	C8—C9—H9	107.3
C6—N2—C9	118.41 (8)	C11—C10—C15	119.09 (12)
C2—C1—C6	119.01 (11)	C11—C10—C9	122.52 (10)
C2—C1—N1	120.58 (11)	C15—C10—C9	118.38 (10)
C6—C1—N1	120.40 (10)	C10—C11—C12	119.33 (15)
C3—C2—C1	120.25 (13)	C10—C11—H11	120.3
C3—C2—H2A	119.9	C12—C11—H11	120.3
C1—C2—H2A	119.9	C13—C12—C11	120.92 (16)
C4—C3—C2	120.84 (13)	C13—C12—H12	119.5
C4—C3—H3	119.6	C11—C12—H12	119.5
C2—C3—H3	119.6	C14—C13—C12	119.71 (14)
C3—C4—C5	119.44 (13)	C14—C13—H13	120.1
C3—C4—H4	120.3	C12—C13—H13	120.1
C5—C4—H4	120.3	C13—C14—C15	120.03 (16)
C4—C5—C6	120.37 (12)	C13—C14—H14	120.0
C4—C5—H5	119.8	C15—C14—H14	120.0
C6—C5—H5	119.8	C14—C15—C10	120.91 (14)
C5—C6—C1	120.05 (10)	C14—C15—H15	119.5
C5—C6—N2	121.01 (10)	C10—C15—H15	119.5
C1—C6—N2	118.94 (9)	O3—C16—N2	120.90 (10)
O1—C7—N1	122.08 (11)	O3—C16—C17	121.05 (11)
O1—C7—C8	121.49 (10)	N2—C16—C17	118.04 (10)
N1—C7—C8	116.36 (9)	C16—C17—H17A	109.5
O2—C8—C7	111.68 (8)	C16—C17—H17B	109.5
O2—C8—C9	110.91 (8)	H17A—C17—H17B	109.5
C7—C8—C9	111.53 (9)	C16—C17—H17C	109.5
O2—C8—H8	107.5	H17A—C17—H17C	109.5
C7—C8—H8	107.5	H17B—C17—H17C	109.5
C9—C8—H8	107.5

C7—N1—C1—C2	−134.65 (15)	C6—N2—C9—C10	−87.10 (10)
C7—N1—C1—C6	45.87 (19)	C16—N2—C9—C8	−145.05 (10)
C6—C1—C2—C3	−1.6 (3)	C6—N2—C9—C8	39.37 (12)
N1—C1—C2—C3	178.87 (17)	O2—C8—C9—N2	173.40 (8)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—N2	48.24 (11)
C2—C3—C4—C5	0.1 (3)	O2—C8—C9—C10	−61.29 (11)
C3—C4—C5—C6	0.7 (3)	C7—C8—C9—C10	173.56 (8)
C4—C5—C6—C1	−2.0 (2)	N2—C9—C10—C11	84.57 (12)
C4—C5—C6—N2	177.86 (14)	C8—C9—C10—C11	−39.79 (14)
C2—C1—C6—C5	2.5 (2)	N2—C9—C10—C15	−94.64 (11)
N1—C1—C6—C5	−178.04 (12)	C8—C9—C10—C15	140.99 (10)
C2—C1—C6—N2	−177.42 (13)	C15—C10—C11—C12	0.26 (18)
N1—C1—C6—N2	2.06 (18)	C9—C10—C11—C12	−178.95 (11)
C16—N2—C6—C5	−67.48 (16)	C10—C11—C12—C13	0.0 (2)
C9—N2—C6—C5	107.89 (12)	C11—C12—C13—C14	−0.5 (2)
C16—N2—C6—C1	112.42 (13)	C12—C13—C14—C15	0.7 (2)
C9—N2—C6—C1	−72.21 (14)	C13—C14—C15—C10	−0.4 (2)
C1—N1—C7—O1	−178.75 (11)	C11—C10—C15—C14	−0.10 (18)
C1—N1—C7—C8	4.08 (17)	C9—C10—C15—C14	179.14 (11)
O1—C7—C8—O2	−18.12 (14)	C6—N2—C16—O3	175.01 (10)
N1—C7—C8—O2	159.07 (10)	C9—N2—C16—O3	−0.35 (16)
O1—C7—C8—C9	106.61 (11)	C6—N2—C16—C17	−6.10 (16)
N1—C7—C8—C9	−76.20 (12)	C9—N2—C16—C17	178.53 (10)
C16—N2—C9—C10	88.48 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃
M_r	296.32
Crystal system, space group	Triclinic, 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)
V (Å³)	719.95 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.29 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19110, 4203, 3584
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.149, 1.02
No. of reflections	4203
No. of parameters	208
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

Acknowledgements

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

References

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