1-Ethyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

Essaghouani, A.; Bouzian, Y.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2414314616006611

organic compounds

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160661

doi:10.1107/S2414314616006611

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1-Ethyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

Abdelhanine Essaghouani,^a ^* Younos Bouzian,^a El Mokhtar Essassi,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014 Avenue Ibn Battouta, Rabat, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: aessaghouani@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 April 2016; accepted 18 April 2016; online 22 April 2016)

The title compound, C₁₇H₁₆N₂O, consists of a benzodiazepin-2-one moiety substituted with a phenyl ring and an ethyl group. The seven-membered diazepine ring has a boat conformation and the fused benzene ring is nearly perpendicular to the phenyl ring, as indicated by the dihedral angle of 74.90 (8)°. The atoms of the ethyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.603 (15):0.397 (15). In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked via a further C—H⋯O hydrogen bond, forming layers parallel to (001), which are in turn linked by C—H⋯π interactions, forming a three-dimensional structure.

Keywords: crystal structure; benzodiazepin-2-one; C—H⋯O hydrogen bonds; C—H⋯π interaction.

CCDC reference: 1474905

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Chemical scheme

Structure description

Benzodiazepines are very important compounds widely used as psychotropic agents (Zellou et al., 1998a ; Kanyonga et al., 2009 ) and hypnotic agents (Zellou et al., 1998b ). Background to the class of 2,3-dihydro-1H-1,5-benzodiazepin-2-ones is given by Ahabchane et al. (2001 ). Continuing our interest in the synthesis of new 1,5-benzodiazepin-2-one derivatives, we report herein on the synthesis and crystal structure of the title compound, obtained under phase-transfer catalysis conditions.

The title compound, Fig. 1, contains a benzodiazepin-2-one moiety, which is linked to a phenyl ring (C10–C15) and to an ethyl group (C6–C7). The seven-membered diazepine ring displays a boat conformation, as indicated by the total puckering amplitude Q_T = 0.918 (2) Å, and spherical polar angle θ = 75.5 (1)°, with φ₂ = 129.4 (2)° and φ3 = −77.0 (4)°. The dihedral angle between the two aromatic ring (C1–C6 and C10–C15) is 74.90 (8)°.

Figure 1
Molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, molecules are linked by C12—H12⋯O1 and C13—H13⋯O1 hydrogen bonds involving the same acceptor atom, forming layers parallel to the ab plane (Fig. 2 and Table 1). The layers are connected by C4—-H4⋯π interactions, building a three-dimensional structure (Fig. 3 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl ring (C10–C15).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.55	3.464 (2)	168
C13—H13⋯O1ⁱⁱ	0.93	2.52	3.412 (2)	162
C4—H4⋯Cg1ⁱⁱⁱ	0.93	2.80	3.568 (1)	140
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A view along the b axis of the crystal packing of the title compound. C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

); H atoms not involved in these interactions have been omitted for clarity.

Figure 3
A partial view of the crystal packing of the title compound, with the C—H⋯O hydrogen bonds and C—H⋯π interactions shown as dashed lines (see Table 1

Synthesis and crystallization

To a solution of 4-phenyl-1, 5-benzodiazepin-2-one (2.36 g, 10 mmol) in DMF (40 ml) was added ethyl bromide (2.16 g, 20 mmol), potassium carbonate (2.77 g, 20 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 colourless crystals (yield 70%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The atoms of the ethyl group (C6 and C7) are disordered over two sets of sites (C6A/C6B and C7A/C7B), with a refined occupancy ratio of 0.603 (15): 0.397 (15).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O
M_r	264.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	16.5042 (4), 9.6896 (3), 18.1221 (5)
V (Å³)	2898.07 (14)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.31 × 0.22

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.626, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	31360, 3199, 2418
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.05
No. of reflections	3199
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.18
Computer programs: APEX2 and SAINT-Plus (Bruker, 2009), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 )ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windoes (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1474905

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314616006611/su4037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006611/su4037Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006611/su4037Isup3.cml

checkCIF report

Experimental top

Structure description top

Benzodiazepines are very important compounds widely used as psychotropic agents (Zellou et al., 1998a; Kanyonga et al., 2009) and hypnotic agents (Zellou et al., 1998b). Background to the class of 2,3-dihydro-1H-1,5-benzodiazepin-2-ones is given by Ahabchane et al. (2001). Continuing our interest in the synthesis of new 1,5-benzodiazepin-2-one derivatives, we report herein on the synthesis and crystal structure of the title compound, obtained by reacting 4-phenyl-1,5-benzodiazepin-2-one with ethyl bromide in phase-transfer catalysis conditions.

The title compound, Fig. 1, contains a benzodiazepin-2-one moiety, which is linked to a phenyl ring (C10–C15) and to an ethyl group (C6–C7). The seven-membered diazepine ring displays a boat conformation, as indicated by the total puckering amplitude Q_T = 0.918 (2) Å, and spherical polar angle θ = 75.5 (1)°, with φ₂ = 129.4 (2)° and φ3 = -77.0 (4)°. The dihedral angle between the two aromatic ring (C1–C6 and C10–C15) is 74.90 (8)°.

In the crystal, molecules are linked by C12—H12···O1 and C13—H13···O1 hydrogen bonds involving the same acceptor atom, forming layers parallel to the ab plane (Fig. 2 and Table 1). The layers are connected by C4—-H4···π interactions, building a three-dimensional structure (Fig. 3 and Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windoes (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009), SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. C—H···O hydrogen bonds are shown as dashed lines (see Table 1); H atoms not involved in these interactions have been omitted for clarity.
	Fig. 3. A partial view of the crystal packing of the title compound, with the C—H···O hydrogen bonds and C—H···π interactions shown as dashed lines (see Table 1).

1-Ethyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one top

Crystal data top

C₁₇H₁₆N₂O	D_x = 1.212 Mg m⁻³
M_r = 264.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3199 reflections
a = 16.5042 (4) Å	θ = 2.6–27.1°
b = 9.6896 (3) Å	µ = 0.08 mm⁻¹
c = 18.1221 (5) Å	T = 296 K
V = 2898.07 (14) Å³	Block, colourless
Z = 8	0.35 × 0.31 × 0.22 mm
F(000) = 1120

Data collection top

Bruker X8 APEX diffractometer	3199 independent reflections
Radiation source: fine-focus sealed tube	2418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 27.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
T_min = 0.626, T_max = 0.746	k = −12→12
31360 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0685P)² + 0.8641P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3199 reflections	Δρ_max = 0.38 e Å⁻³
201 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (7)

Crystal data top

C₁₇H₁₆N₂O	V = 2898.07 (14) Å³
M_r = 264.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.5042 (4) Å	µ = 0.08 mm⁻¹
b = 9.6896 (3) Å	T = 296 K
c = 18.1221 (5) Å	0.35 × 0.31 × 0.22 mm

Data collection top

Bruker X8 APEX diffractometer	3199 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2418 reflections with I > 2σ(I)
T_min = 0.626, T_max = 0.746	R_int = 0.036
31360 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
3199 reflections	Δρ_min = −0.18 e Å⁻³
201 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.39886 (10)	0.78881 (16)	0.79928 (8)	0.0422 (4)
C2	0.35482 (11)	0.7994 (2)	0.86484 (9)	0.0539 (4)
H2	0.2985	0.7990	0.8631	0.065*
C3	0.39311 (12)	0.8103 (2)	0.93194 (9)	0.0577 (5)
H3	0.3627	0.8172	0.9750	0.069*
C4	0.47671 (12)	0.8111 (2)	0.93555 (9)	0.0578 (5)
H4	0.5028	0.8200	0.9808	0.069*
C5	0.52080 (11)	0.79865 (19)	0.87187 (9)	0.0511 (4)
H5	0.5771	0.7972	0.8747	0.061*
C6	0.48392 (10)	0.78807 (15)	0.80279 (8)	0.0402 (3)
C7	0.52244 (9)	0.83690 (15)	0.68217 (8)	0.0382 (3)
C8	0.45039 (9)	0.93206 (16)	0.67409 (9)	0.0434 (4)
H8A	0.4461	0.9925	0.7166	0.052*
H8B	0.4559	0.9884	0.6301	0.052*
C9	0.37702 (10)	0.84114 (18)	0.66843 (9)	0.0473 (4)
C10	0.57784 (9)	0.81512 (17)	0.61856 (8)	0.0417 (4)
C11	0.59420 (10)	0.9202 (2)	0.56865 (9)	0.0524 (4)
H11	0.5685	1.0051	0.5736	0.063*
C12	0.64874 (11)	0.8993 (2)	0.51135 (10)	0.0628 (5)
H12	0.6602	0.9707	0.4787	0.075*
C13	0.68578 (11)	0.7736 (3)	0.50286 (10)	0.0653 (6)
H13	0.7219	0.7596	0.4642	0.078*
C14	0.66943 (11)	0.6682 (2)	0.55163 (11)	0.0629 (5)
H14	0.6943	0.5828	0.5455	0.075*
C15	0.61633 (10)	0.68835 (19)	0.60955 (9)	0.0507 (4)
H15	0.6063	0.6170	0.6426	0.061*
C16A	0.2855 (6)	0.6691 (11)	0.7269 (5)	0.117 (4)	0.603 (15)
H16A	0.2414	0.7031	0.7572	0.140*	0.603 (15)
H16B	0.2663	0.6665	0.6763	0.140*	0.603 (15)
C17A	0.3022 (5)	0.5430 (7)	0.7474 (8)	0.115 (3)	0.603 (15)
H17A	0.2546	0.4867	0.7426	0.172*	0.603 (15)
H17B	0.3446	0.5065	0.7169	0.172*	0.603 (15)
H17C	0.3196	0.5432	0.7980	0.172*	0.603 (15)
C16B	0.2849 (3)	0.6870 (8)	0.7291 (4)	0.0355 (18)	0.397 (15)
H16C	0.2429	0.7284	0.6989	0.043*	0.397 (15)
H16D	0.2637	0.6713	0.7783	0.043*	0.397 (15)
C17B	0.3180 (5)	0.5401 (8)	0.6917 (10)	0.097 (4)	0.397 (15)
H17D	0.2740	0.4758	0.6881	0.146*	0.397 (15)
H17E	0.3393	0.5583	0.6434	0.146*	0.397 (15)
H17F	0.3599	0.5017	0.7222	0.146*	0.397 (15)
N1	0.53607 (8)	0.77094 (14)	0.74201 (7)	0.0431 (3)
N2	0.35601 (8)	0.77348 (15)	0.73142 (7)	0.0493 (4)
O1	0.34016 (9)	0.82593 (16)	0.61053 (7)	0.0717 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0481 (8)	0.0429 (8)	0.0355 (8)	−0.0032 (7)	−0.0018 (6)	0.0032 (6)
C2	0.0507 (9)	0.0656 (11)	0.0455 (9)	−0.0018 (8)	0.0060 (7)	0.0068 (8)
C3	0.0683 (11)	0.0695 (12)	0.0354 (8)	0.0053 (9)	0.0100 (8)	0.0034 (8)
C4	0.0705 (12)	0.0707 (12)	0.0321 (8)	0.0021 (9)	−0.0064 (8)	0.0023 (8)
C5	0.0493 (9)	0.0662 (11)	0.0377 (9)	0.0035 (8)	−0.0054 (7)	0.0056 (8)
C6	0.0481 (8)	0.0397 (8)	0.0328 (7)	0.0034 (6)	−0.0018 (6)	0.0029 (6)
C7	0.0423 (8)	0.0382 (8)	0.0342 (7)	−0.0048 (6)	−0.0035 (6)	−0.0004 (6)
C8	0.0506 (9)	0.0404 (8)	0.0392 (8)	0.0016 (7)	−0.0013 (6)	0.0057 (6)
C9	0.0462 (9)	0.0561 (10)	0.0398 (8)	0.0007 (7)	−0.0067 (7)	0.0027 (7)
C10	0.0402 (8)	0.0521 (9)	0.0327 (7)	−0.0070 (7)	−0.0043 (6)	0.0007 (6)
C11	0.0536 (9)	0.0589 (10)	0.0445 (9)	−0.0093 (8)	−0.0014 (7)	0.0072 (8)
C12	0.0521 (10)	0.0957 (16)	0.0405 (9)	−0.0206 (10)	−0.0021 (8)	0.0151 (9)
C13	0.0397 (9)	0.1147 (18)	0.0415 (9)	−0.0090 (11)	0.0041 (7)	−0.0050 (10)
C14	0.0498 (10)	0.0829 (14)	0.0559 (11)	0.0075 (9)	0.0058 (8)	−0.0085 (10)
C15	0.0473 (9)	0.0604 (10)	0.0445 (9)	0.0027 (8)	0.0036 (7)	0.0011 (8)
C16A	0.164 (8)	0.112 (7)	0.074 (5)	−0.057 (5)	−0.007 (4)	0.013 (5)
C17A	0.114 (4)	0.078 (3)	0.153 (9)	−0.016 (3)	−0.053 (6)	0.006 (4)
C16B	0.013 (2)	0.043 (3)	0.050 (4)	−0.0084 (17)	−0.0139 (19)	0.006 (3)
C17B	0.105 (5)	0.056 (4)	0.131 (9)	−0.012 (3)	−0.027 (6)	−0.012 (5)
N1	0.0454 (7)	0.0496 (7)	0.0342 (7)	0.0037 (6)	−0.0002 (5)	0.0029 (6)
N2	0.0489 (7)	0.0574 (9)	0.0414 (7)	−0.0125 (6)	−0.0063 (6)	0.0044 (6)
O1	0.0691 (9)	0.1001 (11)	0.0459 (7)	−0.0143 (7)	−0.0212 (6)	0.0101 (7)

Geometric parameters (Å, º) top

C1—C2	1.397 (2)	C9—O1	1.2217 (19)
C1—C6	1.405 (2)	C9—N2	1.361 (2)
C1—N2	1.426 (2)	C10—C11	1.389 (2)
C2—C3	1.375 (2)	C10—C15	1.393 (2)
C3—C4	1.381 (3)	C11—C12	1.389 (3)
C4—C5	1.370 (2)	C12—C13	1.371 (3)
C5—C6	1.396 (2)	C13—C14	1.378 (3)
C6—N1	1.408 (2)	C14—C15	1.381 (2)
C7—N1	1.2787 (19)	C16A—C17A	1.307 (11)
C7—C10	1.486 (2)	C16A—N2	1.544 (10)
C7—C8	1.512 (2)	C16B—N2	1.442 (6)
C8—C9	1.501 (2)	C16B—C17B	1.669 (13)

C2—C1—C6	118.80 (14)	C11—C10—C15	118.81 (15)
C2—C1—N2	118.88 (15)	C11—C10—C7	121.38 (15)
C6—C1—N2	122.27 (13)	C15—C10—C7	119.78 (14)
C3—C2—C1	121.26 (16)	C10—C11—C12	120.37 (18)
C2—C3—C4	120.11 (16)	C13—C12—C11	120.18 (18)
C5—C4—C3	119.35 (16)	C12—C13—C14	119.95 (17)
C4—C5—C6	122.04 (16)	C13—C14—C15	120.46 (19)
C5—C6—C1	118.42 (14)	C14—C15—C10	120.22 (17)
C5—C6—N1	116.34 (14)	C17A—C16A—N2	116.0 (7)
C1—C6—N1	125.17 (13)	N2—C16B—C17B	103.9 (5)
N1—C7—C10	118.59 (13)	C7—N1—C6	119.81 (13)
N1—C7—C8	121.69 (14)	C9—N2—C1	123.13 (13)
C10—C7—C8	119.69 (13)	C9—N2—C16B	117.6 (3)
C9—C8—C7	106.45 (13)	C1—N2—C16B	119.3 (3)
O1—C9—N2	122.36 (15)	C9—N2—C16A	117.6 (4)
O1—C9—C8	122.08 (15)	C1—N2—C16A	119.2 (4)
N2—C9—C8	115.52 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the phenyl ring (C10–C15).

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.55	3.464 (2)	168
C13—H13···O1ⁱⁱ	0.93	2.52	3.412 (2)	162
C4—H4···Cg1ⁱⁱⁱ	0.93	2.80	3.568 (1)	140

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the phenyl ring (C10–C15).

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.55	3.464 (2)	168
C13—H13···O1ⁱⁱ	0.93	2.52	3.412 (2)	162
C4—H4···Cg1ⁱⁱⁱ	0.93	2.80	3.568 (1)	140

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O
M_r	264.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	16.5042 (4), 9.6896 (3), 18.1221 (5)
V (Å³)	2898.07 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.31 × 0.22

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.626, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	31360, 3199, 2418
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.05
No. of reflections	3199
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS2014 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windoes (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009), SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Mohammed V, Rabat, Morocco, for financial support.

References

Ahabchane, N. H., Ibrahimi, S., Salem, M., Essassi, E. M., Amzazi, S. & Benjouad, A. (2001). C. R. Acad. Sci. Paris Ser. IIC, 4, 917–924. CAS Google Scholar
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Volume 1| Part 4| April 2016| x160661

doi:10.1107/S2414314616006611

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

1-Ethyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds