1-Ethyl-4-phenyl-1,5-benzodiazepine-2-thione

El Ghayati, L.; Hamou Ahabchane, N.; Lamine Doumbia, M.; Sebbar, N.K.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616019982

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x161998

https://doi.org/10.1107/S2414314616019982

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1-Ethyl-4-phenyl-1,5-benzodiazepine-2-thione

Lhoussaine El Ghayati,^a Noureddine Hamou Ahabchane,^b ^* Mohamadou Lamine Doumbia,^c Nada Kheira Sebbar,^b El Mokhtar Essassi ^b and Joel T. Mague ^d

^aLaboratoire de Chimie Bio Organique Appliqué, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^cUFR Environnement, UNIV Jean Lorougnon Guédé, BP 150, Daloa, Ivory Coast, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: ahabchanenoureddine@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 10 December 2016; accepted 15 December 2016; online 6 January 2017)

In the title compound, C₁₇H₁₆N₂S, the seven-membered ring adopts a boat conformation. The two aromatic rings are inclined at an angle of 34.7 (1)° to one another. The molecules pack in helical chains running along the c-axis direction through C—H⋯S hydrogen bonds. These are further linked into layers parallel to (100) by weak C—H⋯π(ring) interactions. The structure was refined as a two-component inversion twin.

Keywords: crystal structure; benzodiazepine; puckering analysis.

CCDC reference: 1523021

Structure description

1,5-Benzodiazepines have attracted attention as an important class of heterocyclic molecules in medicinal chemistry as drugs and pharmaceuticals. They are widely used as anticonvulsant (Narayana et al., 2006 ), anti-HIV-1 (Di Braccio et al., 2001 ), antimicrobial (Kumar & Joshi, 2007 ) and antitumor agents (Kamal et al., 2008 ). They are also employed as intermediates in the syntheses of several heterocyclic compounds (Minnih et al., 2014 ; Ahabchane et al., 1999 ).

The dihedral angle between the mean planes of the C1–C6 and C10–C15 aromatic rings is 34.7 (1) Å. Puckering analysis of the seven-membered ring (Fig. 1) gave the parameters Q(1) = 0.876 (3) Å, Q(3) = 0.239 (3) Å, φ(2) = 206.8 (2)° and φ(3) = 308.0 (7) and a total puckering amplitude of 0.908 (3) Å. This ring is in a boat conformation.

Figure 1
The title molecule with labeling scheme and 25% probability ellipsoids.

In the crystal, molecules form helical chains running along the c-axis direction through C13—H13⋯S1 hydrogen bonds (Table 1, Figs. 2 and 3). These chains are linked into layers parallel to (100) by weak C8—H8B⋯π(ring) interactions (Table 1, and Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg1ⁱ	0.97	2.92	3.810 (3)	154
C13—H13⋯S1ⁱⁱ	0.97	2.86	3.706 (4)	152
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Figure 2
Detail of the intermolecular interactions [symmetry codes: (i) 1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (ii) $[{3\over 2}]$ − x, 2 − y, $[{1\over 2}]$ + z], with the C—H⋯S and C—H⋯π(ring) interactions shown, respectively, as black and orange dashed lines.

Figure 3
Packing viewed along the a axis. The depiction of the intermolecular interactions is the same as in Fig. 2

Synthesis and crystallization

To a solution of 1-ethyl-4-phenyl-1,5-benzodiazepin-2-one (0.80 g, 3.04 mmol) in 20 ml of pyridine was added phosphorus pentasulfide (0.84 g, 3.65 mmol). The mixture was refluxed for 4 h and the solvent was then evaporated under reduced pressure. The precipitate formed was washed with hot water. The residue obtained was crystallized from ethanol to afford crystals of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as a two-component inversion twin.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂S
M_r	280.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.4001 (8), 9.6239 (9), 18.0037 (18)
V (Å³)	1455.5 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.14 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.83, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	13778, 3544, 2226
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.02
No. of reflections	3544
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.14
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.44 (13)
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1523021

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616019982/sj4080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616019982/sj4080Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019982/sj4080Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019982/sj4080Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-Ethyl-4-phenyl-1,5-benzodiazepine-2-thione top

Crystal data top

C₁₇H₁₆N₂S	D_x = 1.280 Mg m⁻³
M_r = 280.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2911 reflections
a = 8.4001 (8) Å	θ = 2.3–21.0°
b = 9.6239 (9) Å	µ = 0.21 mm⁻¹
c = 18.0037 (18) Å	T = 296 K
V = 1455.5 (2) Å³	Plate, colourless
Z = 4	0.32 × 0.14 × 0.05 mm
F(000) = 592

Data collection top

Bruker SMART APEX CCD diffractometer	3544 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −12→12
T_min = 0.83, T_max = 0.99	l = −23→23
13778 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0489P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3544 reflections	Δρ_max = 0.30 e Å⁻³
183 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.44 (13)

Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F², conventional R–factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F² are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
S1	0.64858 (14)	0.84588 (9)	0.15748 (5)	0.0727 (3)
N1	0.8093 (3)	0.5444 (3)	0.32883 (13)	0.0490 (6)
N3	0.7707 (3)	0.5908 (2)	0.16493 (13)	0.0463 (6)
C1	0.7918 (3)	0.4569 (3)	0.19853 (16)	0.0458 (7)
C2	0.8075 (4)	0.3419 (3)	0.15237 (17)	0.0557 (8)
H2	0.8015	0.3544	0.1012	0.067*
C3	0.8313 (4)	0.2110 (3)	0.17968 (19)	0.0595 (9)
H3	0.8395	0.1358	0.1474	0.071*
C4	0.8432 (4)	0.1910 (4)	0.2555 (2)	0.0634 (9)
H4	0.8578	0.1024	0.2749	0.076*
C5	0.8330 (4)	0.3037 (3)	0.30166 (18)	0.0583 (9)
H5	0.8445	0.2902	0.3525	0.070*
C6	0.8063 (3)	0.4371 (3)	0.27555 (16)	0.0459 (7)
C7	0.7116 (3)	0.6452 (3)	0.32402 (14)	0.0419 (7)
C8	0.5878 (3)	0.6491 (3)	0.26317 (14)	0.0444 (7)
H8A	0.5381	0.5587	0.2577	0.053*
H8B	0.5060	0.7168	0.2748	0.053*
C9	0.6724 (4)	0.6887 (3)	0.19329 (15)	0.0463 (7)
C10	0.7243 (3)	0.7615 (3)	0.37858 (15)	0.0444 (7)
C11	0.6384 (4)	0.8824 (3)	0.37030 (17)	0.0600 (9)
H11	0.5703	0.8926	0.3299	0.072*
C12	0.6525 (5)	0.9886 (4)	0.4214 (2)	0.0727 (10)
H12	0.5944	1.0700	0.4150	0.087*
C13	0.7510 (5)	0.9753 (4)	0.4813 (2)	0.0733 (11)
H13	0.7582	1.0461	0.5162	0.088*
C14	0.8403 (5)	0.8549 (4)	0.48946 (16)	0.0657 (9)
H14	0.9092	0.8459	0.5296	0.079*
C15	0.8274 (4)	0.7485 (3)	0.43846 (15)	0.0551 (8)
H15	0.8878	0.6682	0.4442	0.066*
C16	0.8645 (4)	0.6230 (3)	0.09777 (15)	0.0586 (9)
H16A	0.9555	0.5611	0.0961	0.070*
H16B	0.9049	0.7171	0.1021	0.070*
C17	0.7743 (5)	0.6106 (4)	0.02465 (17)	0.0767 (12)
H17A	0.8460	0.6265	−0.0160	0.115*
H17B	0.6903	0.6782	0.0233	0.115*
H17C	0.7296	0.5191	0.0205	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1136 (8)	0.0476 (5)	0.0567 (5)	0.0110 (5)	0.0115 (5)	0.0089 (4)
N1	0.0552 (15)	0.0485 (14)	0.0431 (13)	0.0009 (13)	−0.0045 (12)	0.0021 (11)
N3	0.0532 (14)	0.0441 (14)	0.0416 (13)	−0.0043 (11)	0.0024 (12)	−0.0025 (11)
C1	0.0447 (17)	0.0413 (15)	0.0515 (17)	−0.0010 (15)	−0.0002 (14)	−0.0027 (14)
C2	0.063 (2)	0.0537 (18)	0.0505 (16)	0.0001 (17)	0.0022 (16)	−0.0089 (16)
C3	0.0574 (19)	0.0484 (18)	0.073 (2)	0.0050 (16)	0.0027 (18)	−0.0126 (16)
C4	0.059 (2)	0.048 (2)	0.083 (2)	0.0093 (18)	0.002 (2)	0.0082 (16)
C5	0.061 (2)	0.057 (2)	0.0566 (19)	0.0122 (18)	−0.0054 (18)	0.0058 (15)
C6	0.0458 (17)	0.0451 (17)	0.0470 (17)	0.0041 (14)	−0.0011 (13)	−0.0007 (13)
C7	0.0493 (17)	0.0406 (15)	0.0357 (14)	−0.0022 (14)	0.0014 (12)	0.0042 (13)
C8	0.0477 (17)	0.0422 (16)	0.0434 (15)	−0.0016 (14)	−0.0009 (13)	−0.0019 (14)
C9	0.0539 (18)	0.0478 (17)	0.0373 (14)	−0.0023 (15)	−0.0051 (14)	−0.0025 (12)
C10	0.0495 (17)	0.0470 (17)	0.0367 (14)	−0.0047 (14)	0.0036 (14)	0.0024 (13)
C11	0.074 (2)	0.055 (2)	0.0511 (17)	0.0073 (18)	−0.0063 (16)	−0.0062 (14)
C12	0.088 (3)	0.059 (2)	0.071 (2)	0.010 (2)	0.000 (2)	−0.0149 (18)
C13	0.100 (3)	0.069 (3)	0.050 (2)	−0.017 (2)	0.008 (2)	−0.0172 (19)
C14	0.084 (2)	0.073 (2)	0.0404 (16)	−0.016 (2)	−0.0088 (17)	0.0011 (17)
C15	0.068 (2)	0.0562 (19)	0.0408 (15)	−0.0064 (18)	−0.0014 (17)	0.0056 (14)
C16	0.073 (2)	0.060 (2)	0.0430 (16)	−0.0084 (18)	0.0098 (15)	−0.0030 (15)
C17	0.116 (3)	0.071 (3)	0.0430 (18)	−0.006 (2)	0.007 (2)	−0.0023 (17)

Geometric parameters (Å, º) top

S1—C9	1.657 (3)	C8—H8A	0.9700
N1—C7	1.274 (3)	C8—H8B	0.9700
N1—C6	1.409 (4)	C10—C11	1.377 (4)
N3—C9	1.353 (4)	C10—C15	1.389 (4)
N3—C1	1.434 (4)	C11—C12	1.380 (4)
N3—C16	1.476 (4)	C11—H11	0.9300
C1—C2	1.391 (4)	C12—C13	1.364 (5)
C1—C6	1.405 (4)	C12—H12	0.9300
C2—C3	1.367 (4)	C13—C14	1.388 (5)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.383 (5)	C14—C15	1.380 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.368 (5)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.524 (4)
C5—C6	1.386 (4)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C7—C10	1.493 (4)	C17—H17A	0.9600
C7—C8	1.511 (4)	C17—H17B	0.9600
C8—C9	1.494 (4)	C17—H17C	0.9600

C7—N1—C6	120.0 (2)	N3—C9—S1	124.2 (2)
C9—N3—C1	122.8 (2)	C8—C9—S1	120.2 (2)
C9—N3—C16	119.3 (2)	C11—C10—C15	119.1 (3)
C1—N3—C16	117.9 (2)	C11—C10—C7	121.7 (3)
C2—C1—C6	118.3 (3)	C15—C10—C7	119.2 (3)
C2—C1—N3	118.4 (3)	C10—C11—C12	120.6 (3)
C6—C1—N3	123.3 (2)	C10—C11—H11	119.7
C3—C2—C1	122.2 (3)	C12—C11—H11	119.7
C3—C2—H2	118.9	C13—C12—C11	120.6 (3)
C1—C2—H2	118.9	C13—C12—H12	119.7
C2—C3—C4	119.6 (3)	C11—C12—H12	119.7
C2—C3—H3	120.2	C12—C13—C14	119.4 (3)
C4—C3—H3	120.2	C12—C13—H13	120.3
C5—C4—C3	119.0 (3)	C14—C13—H13	120.3
C5—C4—H4	120.5	C15—C14—C13	120.4 (3)
C3—C4—H4	120.5	C15—C14—H14	119.8
C4—C5—C6	122.6 (3)	C13—C14—H14	119.8
C4—C5—H5	118.7	C14—C15—C10	119.9 (3)
C6—C5—H5	118.7	C14—C15—H15	120.0
C5—C6—C1	118.3 (3)	C10—C15—H15	120.0
C5—C6—N1	116.4 (3)	N3—C16—C17	115.2 (3)
C1—C6—N1	125.0 (2)	N3—C16—H16A	108.5
N1—C7—C10	118.7 (2)	C17—C16—H16A	108.5
N1—C7—C8	120.8 (2)	N3—C16—H16B	108.5
C10—C7—C8	120.5 (2)	C17—C16—H16B	108.5
C9—C8—C7	106.8 (2)	H16A—C16—H16B	107.5
C9—C8—H8A	110.4	C16—C17—H17A	109.5
C7—C8—H8A	110.4	C16—C17—H17B	109.5
C9—C8—H8B	110.4	H17A—C17—H17B	109.5
C7—C8—H8B	110.4	C16—C17—H17C	109.5
H8A—C8—H8B	108.6	H17A—C17—H17C	109.5
N3—C9—C8	115.5 (2)	H17B—C17—H17C	109.5

C9—N3—C1—C2	141.7 (3)	C1—N3—C9—C8	0.8 (4)
C16—N3—C1—C2	−40.1 (4)	C16—N3—C9—C8	−177.4 (3)
C9—N3—C1—C6	−41.9 (4)	C1—N3—C9—S1	178.2 (2)
C16—N3—C1—C6	136.3 (3)	C16—N3—C9—S1	0.0 (4)
C6—C1—C2—C3	2.0 (5)	C7—C8—C9—N3	70.5 (3)
N3—C1—C2—C3	178.6 (3)	C7—C8—C9—S1	−107.0 (3)
C1—C2—C3—C4	−1.1 (5)	N1—C7—C10—C11	170.5 (3)
C2—C3—C4—C5	−1.0 (5)	C8—C7—C10—C11	−7.9 (4)
C3—C4—C5—C6	2.1 (6)	N1—C7—C10—C15	−8.3 (4)
C4—C5—C6—C1	−1.1 (5)	C8—C7—C10—C15	173.2 (3)
C4—C5—C6—N1	−175.8 (3)	C15—C10—C11—C12	−1.0 (5)
C2—C1—C6—C5	−0.9 (4)	C7—C10—C11—C12	−179.8 (3)
N3—C1—C6—C5	−177.3 (3)	C10—C11—C12—C13	−0.4 (6)
C2—C1—C6—N1	173.3 (3)	C11—C12—C13—C14	1.6 (6)
N3—C1—C6—N1	−3.1 (5)	C12—C13—C14—C15	−1.3 (6)
C7—N1—C6—C5	−142.0 (3)	C13—C14—C15—C10	−0.2 (5)
C7—N1—C6—C1	43.7 (4)	C11—C10—C15—C14	1.3 (5)
C6—N1—C7—C10	−176.3 (2)	C7—C10—C15—C14	−179.8 (3)
C6—N1—C7—C8	2.1 (4)	C9—N3—C16—C17	−80.5 (3)
N1—C7—C8—C9	−75.7 (3)	C1—N3—C16—C17	101.3 (3)
C10—C7—C8—C9	102.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg1ⁱ	0.97	2.92	3.810 (3)	154
C13—H13···S1ⁱⁱ	0.97	2.86	3.706 (4)	152

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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ISSN: 2414-3146

Volume 2| Part 1| January 2017| x161998

https://doi.org/10.1107/S2414314616019982

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

1-Ethyl-4-phenyl-1,5-benzodiazepine-2-thione

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds