(4Z)-4-(2-Oxo­propyl­idene)-1,3-bis­(prop-2-en-1-yl)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

Sebhaoui, J.; El Bakri, Y.; Rayni, I.; El Bourakadi, K.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S241431461700493X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170493

https://doi.org/10.1107/S241431461700493X

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(4Z)-4-(2-Oxopropylidene)-1,3-bis(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Jihad Sebhaoui,^a ^* Youness El Bakri,^a Ibtissam Rayni,^a Khadija El Bourakadi,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: sebhaoui.jihad@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 27 March 2017; accepted 29 March 2017; online 4 April 2017)

In the title compound, C₁₈H₂₀N₂O₂, the diazepin-2-one ring adopts a tub conformation. The conformation of the acetyl group is partially determined by an intramolecular N—H⋯O hydrogen bond. In the crystal, pairwise C—H⋯O hydrogen bonds form inversion dimers.

Keywords: crystal structure; hydrogen bond; diazepine; crystal structure.

CCDC reference: 1541017

Structure description

1,5-Benzodiazepine derivatives have attracted much attention as they exhibit pronounced anxiolytic, sedative, hypnotic and anticonvulsant activities with low toxicity (Landquist et al., 1984 ; Hamor et al., 1984 ; Ben-Cherif et al., 2010 ). They are also used as an intermediates for the synthesis of new heterocyclic systems (Ahabchane et al., 2001 ; Minnih et al., 2014 ). In a continuation of our work on the synthesis and structure of 1,5-benzodiazepine derivatives (Sebhaoui et al., 2016 ), we report here the preparation and crystal structure of the title compound.

The seven-membered ring adopts a tub conformation. Puckering analysis of the conformation gave the parameters Q(2) = 0.891 (1) Å, Q(3) = 0.295 (1) Å, φ(2) = 204.93 (7)° and φ(3) = 311.0 (2)° with a total puckering amplitude of 0.928 (1) Å. The orientation of the acetyl substituent is determined in part by the intramolecular N1—H1⋯O2 hydrogen bond (Table 1 and Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.910 (17)	1.878 (16)	2.6308 (12)	138.6 (14)
C10—H10⋯O1ⁱ	0.977 (14)	2.567 (14)	3.5316 (13)	168.9 (11)
Symmetry code: (i) -x+1, -y+2, -z+1.

Figure 1
The title molecule with the labeling scheme and 50% probability ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.

In the crystal, molecules form inversion dimers through complementary C10—H10⋯O1ⁱ hydrogen bonds (Table 1 and Fig. 2).

Figure 2
Packing projected onto (001) with intermolecular C—H⋯O hydrogen bonds shown as dashed lines.

Synthesis and crystallization

To a solution of (4Z)-4-(-2-oxopropylidene)-1,5-benzodiazepin-2-one (0.01 mol) in 60 ml of N,N-dimethylformamide were added K₂CO₃ (0.02 mol), allyl bromide (0.02 mol) and tetra n-butylammonium bromide (TBAB) (0.001 mol). The reaction mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The residue was chromatographed on a silica gel column using hexane and ethyl acetate (90/10) as eluents to afford the title compound as colourless crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₂
M_r	296.36
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	8.6864 (6), 8.9925 (6), 10.9872 (7)
α, β, γ (°)	110.653 (1), 95.111 (1), 104.723 (1)
V (Å³)	761.42 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.88, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	14767, 4041, 3219
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.09
No. of reflections	4041
No. of parameters	279
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.24
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 )and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1541017

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431461700493X/sj4101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700493X/sj4101Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700493X/sj4101Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S241431461700493X/sj4101Isup4.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: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(4Z)-4-(2-Oxopropylidene)-1,3-bis(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top

Crystal data top

C₁₈H₂₀N₂O₂	Z = 2
M_r = 296.36	F(000) = 316
Triclinic, P1	D_x = 1.293 Mg m⁻³
a = 8.6864 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9925 (6) Å	Cell parameters from 6420 reflections
c = 10.9872 (7) Å	θ = 2.5–29.2°
α = 110.653 (1)°	µ = 0.09 mm⁻¹
β = 95.111 (1)°	T = 100 K
γ = 104.723 (1)°	Block, colourless
V = 761.42 (9) Å³	0.36 × 0.25 × 0.25 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4041 independent reflections
Radiation source: fine-focus sealed tube	3219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −12→12
T_min = 0.88, T_max = 0.98	l = −14→15
14767 measured reflections

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.128	All H-atom parameters refined
S = 1.09	w = 1/[σ²(F_o²) + (0.0798P)² + 0.0641P] where P = (F_o² + 2F_c²)/3
4041 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 10 sec/frame.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.72540 (10)	0.99583 (9)	0.37759 (8)	0.01874 (19)
O2	0.68608 (10)	0.68232 (10)	0.74999 (8)	0.0219 (2)
N1	0.73630 (11)	0.63488 (11)	0.50839 (9)	0.0149 (2)
H1	0.7503 (19)	0.6185 (19)	0.5852 (17)	0.033 (4)*
N2	0.86150 (10)	0.80420 (10)	0.33693 (9)	0.0134 (2)
C1	0.87072 (12)	0.64209 (12)	0.32073 (10)	0.0137 (2)
C2	0.95114 (13)	0.56478 (14)	0.22408 (11)	0.0183 (2)
H2	0.9908 (17)	0.6174 (17)	0.1664 (14)	0.020 (3)*
C3	0.97350 (14)	0.41321 (15)	0.21084 (12)	0.0218 (3)
H3	1.0298 (19)	0.3623 (19)	0.1449 (16)	0.032 (4)*
C4	0.91651 (14)	0.33589 (14)	0.29426 (12)	0.0205 (2)
H4	0.9307 (18)	0.2294 (19)	0.2830 (15)	0.031 (4)*
C5	0.83713 (13)	0.41063 (13)	0.39037 (11)	0.0171 (2)
H5	0.7977 (16)	0.3598 (16)	0.4529 (14)	0.018 (3)*
C6	0.81244 (12)	0.56313 (13)	0.40477 (10)	0.0137 (2)
C7	0.62363 (12)	0.71296 (12)	0.50155 (10)	0.0137 (2)
C8	0.58137 (12)	0.72269 (13)	0.36870 (10)	0.0144 (2)
H8	0.5736 (17)	0.6142 (17)	0.2981 (14)	0.022 (4)*
C9	0.72664 (12)	0.85397 (13)	0.36026 (10)	0.0135 (2)
C10	0.55651 (13)	0.77944 (13)	0.60908 (11)	0.0157 (2)
H10	0.4772 (17)	0.8366 (17)	0.5993 (14)	0.022 (3)*
C11	0.59228 (13)	0.76065 (13)	0.73184 (11)	0.0173 (2)
C12	0.51378 (16)	0.83951 (17)	0.84424 (12)	0.0249 (3)
H12A	0.469 (2)	0.760 (2)	0.881 (2)	0.059 (6)*
H12B	0.435 (2)	0.891 (2)	0.8239 (16)	0.037 (4)*
H12C	0.605 (2)	0.933 (2)	0.916 (2)	0.051 (5)*
C13	0.42116 (13)	0.75818 (14)	0.34215 (11)	0.0178 (2)
H13A	0.3311 (17)	0.6712 (17)	0.3594 (14)	0.023 (3)*
H13B	0.4255 (16)	0.8713 (17)	0.4069 (14)	0.021 (3)*
C14	0.38388 (15)	0.74770 (17)	0.20244 (13)	0.0248 (3)
H14	0.399 (2)	0.850 (3)	0.190 (2)	0.065 (6)*
C15	0.3403 (2)	0.6128 (2)	0.09694 (15)	0.0432 (4)
H15A	0.318 (3)	0.505 (3)	0.102 (3)	0.097 (8)*
H15B	0.318 (2)	0.616 (2)	0.0088 (19)	0.050 (5)*
C16	1.00249 (13)	0.92304 (13)	0.32234 (11)	0.0162 (2)
H16A	1.0122 (16)	1.0332 (17)	0.3896 (13)	0.017 (3)*
H16B	1.0997 (17)	0.8951 (17)	0.3466 (13)	0.023 (4)*
C17	0.99218 (14)	0.92956 (14)	0.18704 (11)	0.0195 (2)
H17	1.0916 (19)	1.0012 (19)	0.1798 (15)	0.033 (4)*
C18	0.86578 (16)	0.85178 (15)	0.08827 (12)	0.0234 (3)
H18A	0.762 (2)	0.7781 (19)	0.0972 (16)	0.034 (4)*
H18B	0.8730 (19)	0.8666 (18)	0.0047 (16)	0.029 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0221 (4)	0.0158 (4)	0.0216 (4)	0.0089 (3)	0.0064 (3)	0.0084 (3)
O2	0.0257 (4)	0.0262 (4)	0.0194 (4)	0.0122 (3)	0.0063 (3)	0.0118 (3)
N1	0.0165 (4)	0.0167 (4)	0.0158 (4)	0.0082 (3)	0.0050 (3)	0.0088 (4)
N2	0.0140 (4)	0.0125 (4)	0.0154 (4)	0.0049 (3)	0.0045 (3)	0.0063 (3)
C1	0.0132 (5)	0.0134 (5)	0.0147 (5)	0.0056 (4)	0.0010 (4)	0.0050 (4)
C2	0.0195 (5)	0.0215 (5)	0.0171 (5)	0.0101 (4)	0.0056 (4)	0.0080 (4)
C3	0.0236 (6)	0.0237 (6)	0.0197 (6)	0.0147 (5)	0.0057 (4)	0.0048 (4)
C4	0.0202 (5)	0.0162 (5)	0.0251 (6)	0.0098 (4)	0.0017 (4)	0.0055 (4)
C5	0.0154 (5)	0.0151 (5)	0.0220 (6)	0.0050 (4)	0.0021 (4)	0.0086 (4)
C6	0.0127 (4)	0.0144 (5)	0.0143 (5)	0.0053 (4)	0.0021 (4)	0.0051 (4)
C7	0.0121 (5)	0.0123 (4)	0.0166 (5)	0.0026 (4)	0.0024 (4)	0.0066 (4)
C8	0.0139 (5)	0.0154 (5)	0.0152 (5)	0.0055 (4)	0.0031 (4)	0.0067 (4)
C9	0.0159 (5)	0.0158 (5)	0.0101 (5)	0.0062 (4)	0.0028 (4)	0.0055 (4)
C10	0.0142 (5)	0.0160 (5)	0.0181 (5)	0.0055 (4)	0.0042 (4)	0.0072 (4)
C11	0.0165 (5)	0.0159 (5)	0.0179 (5)	0.0025 (4)	0.0045 (4)	0.0062 (4)
C12	0.0276 (6)	0.0321 (7)	0.0188 (6)	0.0135 (5)	0.0103 (5)	0.0100 (5)
C13	0.0151 (5)	0.0201 (5)	0.0197 (5)	0.0077 (4)	0.0025 (4)	0.0082 (4)
C14	0.0236 (6)	0.0300 (6)	0.0258 (6)	0.0099 (5)	0.0021 (5)	0.0160 (5)
C15	0.0613 (10)	0.0369 (8)	0.0230 (7)	0.0013 (7)	0.0004 (7)	0.0135 (6)
C16	0.0142 (5)	0.0165 (5)	0.0179 (5)	0.0028 (4)	0.0032 (4)	0.0078 (4)
C17	0.0223 (6)	0.0203 (5)	0.0212 (6)	0.0085 (4)	0.0103 (4)	0.0115 (4)
C18	0.0317 (6)	0.0260 (6)	0.0165 (6)	0.0135 (5)	0.0072 (5)	0.0091 (5)

Geometric parameters (Å, º) top

O1—C9	1.2247 (13)	C8—H8	0.991 (14)
O2—C11	1.2496 (14)	C10—C11	1.4343 (16)
N1—C7	1.3527 (13)	C10—H10	0.977 (14)
N1—C6	1.4081 (14)	C11—C12	1.5070 (16)
N1—H1	0.910 (17)	C12—H12A	0.96 (2)
N2—C9	1.3701 (13)	C12—H12B	0.965 (17)
N2—C1	1.4290 (13)	C12—H12C	1.02 (2)
N2—C16	1.4690 (13)	C13—C14	1.5047 (17)
C1—C2	1.3990 (15)	C13—H13A	1.039 (14)
C1—C6	1.4058 (15)	C13—H13B	1.003 (14)
C2—C3	1.3843 (16)	C14—C15	1.287 (2)
C2—H2	0.954 (14)	C14—H14	0.96 (2)
C3—C4	1.3871 (18)	C15—H15A	0.97 (3)
C3—H3	0.958 (16)	C15—H15B	0.983 (19)
C4—C5	1.3808 (16)	C16—C17	1.5039 (16)
C4—H4	0.963 (15)	C16—H16A	0.982 (13)
C5—C6	1.3979 (15)	C16—H16B	0.980 (14)
C5—H5	0.991 (14)	C17—C18	1.3170 (17)
C7—C10	1.3765 (15)	C17—H17	0.966 (16)
C7—C8	1.5113 (15)	C18—H18A	1.010 (16)
C8—C9	1.5282 (14)	C18—H18B	0.979 (16)
C8—C13	1.5306 (14)

C7—N1—C6	126.14 (9)	C7—C10—C11	122.55 (10)
C7—N1—H1	113.1 (10)	C7—C10—H10	118.3 (8)
C6—N1—H1	120.2 (10)	C11—C10—H10	119.0 (8)
C9—N2—C1	124.02 (9)	O2—C11—C10	122.97 (10)
C9—N2—C16	117.67 (9)	O2—C11—C12	118.49 (10)
C1—N2—C16	118.26 (8)	C10—C11—C12	118.54 (10)
C2—C1—C6	118.84 (10)	C11—C12—H12A	109.2 (12)
C2—C1—N2	118.71 (9)	C11—C12—H12B	115.9 (10)
C6—C1—N2	122.27 (9)	H12A—C12—H12B	111.7 (15)
C3—C2—C1	120.93 (11)	C11—C12—H12C	106.4 (11)
C3—C2—H2	119.7 (8)	H12A—C12—H12C	107.0 (16)
C1—C2—H2	119.4 (8)	H12B—C12—H12C	106.3 (14)
C2—C3—C4	120.12 (11)	C14—C13—C8	111.01 (9)
C2—C3—H3	120.0 (9)	C14—C13—H13A	111.2 (8)
C4—C3—H3	119.8 (9)	C8—C13—H13A	107.2 (8)
C5—C4—C3	119.71 (10)	C14—C13—H13B	109.9 (8)
C5—C4—H4	120.8 (9)	C8—C13—H13B	110.4 (8)
C3—C4—H4	119.5 (9)	H13A—C13—H13B	106.9 (11)
C4—C5—C6	121.04 (11)	C15—C14—C13	125.60 (13)
C4—C5—H5	121.5 (8)	C15—C14—H14	116.5 (13)
C6—C5—H5	117.4 (8)	C13—C14—H14	117.8 (13)
C5—C6—C1	119.36 (10)	C14—C15—H15A	121.2 (16)
C5—C6—N1	117.77 (10)	C14—C15—H15B	120.8 (10)
C1—C6—N1	122.80 (9)	H15A—C15—H15B	117.7 (19)
N1—C7—C10	121.64 (10)	N2—C16—C17	114.66 (9)
N1—C7—C8	114.62 (9)	N2—C16—H16A	106.5 (8)
C10—C7—C8	123.73 (9)	C17—C16—H16A	110.0 (8)
C7—C8—C9	105.81 (8)	N2—C16—H16B	107.8 (8)
C7—C8—C13	115.83 (9)	C17—C16—H16B	110.9 (8)
C9—C8—C13	112.20 (9)	H16A—C16—H16B	106.5 (11)
C7—C8—H8	108.3 (8)	C18—C17—C16	126.31 (11)
C9—C8—H8	107.4 (8)	C18—C17—H17	122.1 (10)
C13—C8—H8	106.9 (8)	C16—C17—H17	111.6 (10)
O1—C9—N2	121.96 (10)	C17—C18—H18A	121.5 (9)
O1—C9—C8	122.65 (9)	C17—C18—H18B	118.9 (9)
N2—C9—C8	115.34 (9)	H18A—C18—H18B	119.6 (13)

C9—N2—C1—C2	140.12 (10)	N1—C7—C8—C13	161.42 (9)
C16—N2—C1—C2	−37.25 (14)	C10—C7—C8—C13	−19.55 (14)
C9—N2—C1—C6	−44.67 (15)	C1—N2—C9—O1	177.73 (9)
C16—N2—C1—C6	137.96 (10)	C16—N2—C9—O1	−4.89 (15)
C6—C1—C2—C3	−0.03 (16)	C1—N2—C9—C8	0.13 (14)
N2—C1—C2—C3	175.35 (10)	C16—N2—C9—C8	177.51 (9)
C1—C2—C3—C4	−0.25 (18)	C7—C8—C9—O1	−103.13 (11)
C2—C3—C4—C5	0.12 (18)	C13—C8—C9—O1	24.08 (14)
C3—C4—C5—C6	0.29 (17)	C7—C8—C9—N2	74.45 (11)
C4—C5—C6—C1	−0.56 (16)	C13—C8—C9—N2	−158.34 (9)
C4—C5—C6—N1	−177.52 (10)	N1—C7—C10—C11	−4.46 (16)
C2—C1—C6—C5	0.43 (15)	C8—C7—C10—C11	176.57 (10)
N2—C1—C6—C5	−174.78 (9)	C7—C10—C11—O2	−0.30 (17)
C2—C1—C6—N1	177.22 (10)	C7—C10—C11—C12	179.43 (10)
N2—C1—C6—N1	2.01 (15)	C7—C8—C13—C14	−174.24 (9)
C7—N1—C6—C5	−139.68 (11)	C9—C8—C13—C14	64.13 (12)
C7—N1—C6—C1	43.48 (15)	C8—C13—C14—C15	71.29 (18)
C6—N1—C7—C10	−179.89 (10)	C9—N2—C16—C17	−81.22 (12)
C6—N1—C7—C8	−0.83 (14)	C1—N2—C16—C17	96.32 (11)
N1—C7—C8—C9	−73.60 (11)	N2—C16—C17—C18	6.42 (17)
C10—C7—C8—C9	105.44 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.910 (17)	1.878 (16)	2.6308 (12)	138.6 (14)
C10—H10···O1ⁱ	0.977 (14)	2.567 (14)	3.5316 (13)	168.9 (11)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

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

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