3-Hy­droxy-4-phenyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one: cis isomer

Rida, M.; El Bakri, Y.; Doumbia, M.L.; Benchidmi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616018794

organic compounds

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ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161879

https://doi.org/10.1107/S2414314616018794

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3-Hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one: cis isomer

Mohammed Rida,^a ^* Youness El Bakri,^a Mohamadou Lamine Doumbia,^b Mohammed Benchidmi,^a El Mokhtar Essassi ^a and Joel T Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, ^bUFR-Environnement, UNIV Jean Lorougnon Guédé, BP 150, Daloa, Ivory Coast, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: rida.m.b@hotmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 November 2016; accepted 23 November 2016; online 29 November 2016)

In the title compound, C₁₅H₁₄N₂O₂, the seven-membered benzodiazepine ring adopts a twist-boat conformation and the two aromatic rings are inclined to one another by 81.06 (15)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains propagating along the [10-1] direction. The chains are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane. Within the sheets, there are N—H⋯π interactions present, and C—H⋯π interactions link the sheets to form a three-dimensional structure.

Keywords: crystal structure; benzodiazepine; cis isomer; hydrogen bonding; N—H⋯π interactions; C—H⋯π interactions.

CCDC reference: 1518908

Structure description

1,5-Benzodiazepine derivatives have been used as therapeutics for viral infections and cardiovascular disorder (Jacob et al., 2011 ; Maleki et al., 2014 ). They are active against potassium blockers (Claremon et al., 1996 ) and are also employed as intermediates for the synthesis of several heterocyclic compounds (Minnih et al., 2014 ; Ahabchane et al., 1999 ). As part of our studies in this area, we now describe the synthesis and crystal structure of the title compound, Fig. 1.

Figure 1
The molecular structure of the title compound, with the atom labelling and 50% probability ellipsoids.

The seven-membered ring (N1/N2/C1/C6–C9) adopts a twist-boat conformation [puckering parameters: Q(2) = 0.571 (3) Å, Q(3) = 0.375 (3) Å, φ(2) = 230.7 (3)° and φ(3) = 326.7 (5)°; total puckering amplitude Q = 0.682 (3) Å]. The dihedral angle between the aromatic rings, C1–C6 and C10–C15, is 81.06 (15)°. There is possibly an intramolecular O1—H1⋯O2 hydrogen bond (Table 1), but the small O—H⋯O angle of 122 (4)° would indicate considerable strain.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (4)	2.01 (4)	2.556 (3)	122 (4)
N2—H2A⋯O1ⁱ	0.88 (4)	2.09 (4)	2.922 (3)	157 (3)
C8—H8⋯O2ⁱⁱ	0.99 (4)	2.57 (4)	3.395 (4)	141 (3)
C12—H12⋯Cg1ⁱⁱⁱ	0.99 (4)	2.85 (3)	3.696 (4)	144 (3)
N1—H1A⋯Cg2ⁱⁱ	0.99 (5)	2.63 (3)	3.457 (3)	149 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

In the crystal, molecules are linked by N2—H2A⋯O1ⁱ hydrogen bonds, forming chains propagating along [10 $[\overline{1}]$ ]; see Table 1 and Fig. 2. The chains are linked by C8—H8⋯O2ⁱⁱ hydrogen bonds, forming sheets parallel to the ac plane (Table 1 and Fig. 2). Within the sheets there are N—H⋯π interactions present, and C—H⋯π interactions link the sheets to form a three-dimensional structure (Table 1 and Fig. 3).

Figure 2
The crystal packing of the title compound, viewed along the a-axis direction. Hydrogen bonds are shown as dashed lines (see Table 1

Figure 3
Details of the intermolecular N—H⋯O (blue dotted lines) and C—H⋯O (black dotted line) hydrogen bonds, as well as the N—H⋯π(ring) (purple dotted line) and C—H⋯π(ring) (orange dotted lines) interactions. [Symmetry codes: (i) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z; (ii) $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z; (iii) 1 − x, 1 − y, 1 − z); (iv) 1 + x, y, z.]

Synthesis and crystallization

A mixture of o-phenylenediamine 1 (0.03 mol) and ethyl glycidate (0.03 mol) was refluxed in 80 ml of xylene for 48 h. The resulting crude mixture was left at room temperature overnight. The trans diastereoisomer which precipitated was filtered. The filtrate was concentrated under reduced pressure and the oil obtained was chromatographed on a silica gel column with a mixture of ether/chloroform (50/50) as eluent, and gave the trans and cis isomers, with a predominance of the trans isomers. The cis isomer was recrystallized from ethanol solution 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	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	5.519 (2), 21.594 (8), 9.917 (4)
β (°)	90.405 (5)
V (Å³)	1181.9 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.17 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.69, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	10886, 2955, 2064
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.211, 1.10
No. of reflections	2955
No. of parameters	228
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.37
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: 1518908

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616018794/su4096sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018794/su4096Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018794/su4096Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018794/su4096Isup4.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).

3-Hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top

Crystal data top

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.519 (2) Å	Cell parameters from 2522 reflections
b = 21.594 (8) Å	θ = 2.3–27.3°
c = 9.917 (4) Å	µ = 0.10 mm⁻¹
β = 90.405 (5)°	T = 100 K
V = 1181.9 (7) Å³	Plate, colourless
Z = 4	0.41 × 0.17 × 0.09 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2955 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.5°, θ_min = 1.9°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −28→28
T_min = 0.69, T_max = 0.99	l = −13→13
10886 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)] = 0.084	Hydrogen site location: difference Fourier map
wR(F²) = 0.211	All H-atom parameters refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0375P)² + 2.6752P] where P = (F_o² + 2F_c²)/3
2955 reflections	(Δ/σ)_max = 0.002
228 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
O1	0.7374 (4)	0.22601 (11)	0.6710 (2)	0.0243 (5)
H1	0.597 (8)	0.2125 (19)	0.656 (4)	0.037 (11)*
O2	0.3865 (4)	0.24635 (11)	0.5074 (2)	0.0259 (5)
N1	1.0082 (5)	0.36774 (14)	0.5379 (3)	0.0231 (6)
H1A	1.152 (8)	0.385 (2)	0.567 (4)	0.043 (12)*
N2	0.5741 (5)	0.31730 (13)	0.3793 (3)	0.0224 (6)
H2A	0.447 (6)	0.3124 (15)	0.326 (3)	0.016 (8)*
C1	0.7618 (5)	0.35486 (15)	0.3285 (3)	0.0207 (6)
C2	0.7369 (6)	0.37111 (16)	0.1921 (3)	0.0231 (7)
H2	0.605 (7)	0.3557 (16)	0.148 (4)	0.023 (9)*
C3	0.8982 (6)	0.40866 (16)	0.1277 (3)	0.0257 (7)
H3	0.872 (7)	0.4181 (18)	0.037 (4)	0.035 (10)*
C4	1.0966 (6)	0.43153 (17)	0.1999 (3)	0.0263 (7)
H4	1.206 (7)	0.4591 (17)	0.161 (4)	0.027 (9)*
C5	1.1238 (5)	0.41670 (16)	0.3341 (3)	0.0238 (7)
H5	1.271 (7)	0.4331 (16)	0.387 (4)	0.025 (9)*
C6	0.9597 (5)	0.37839 (15)	0.4029 (3)	0.0205 (6)
C7	0.8692 (5)	0.33250 (15)	0.6340 (3)	0.0208 (7)
H7	0.985 (6)	0.3219 (15)	0.709 (3)	0.015 (8)*
C8	0.7900 (5)	0.27039 (15)	0.5704 (3)	0.0213 (7)
H8	0.923 (7)	0.2558 (16)	0.512 (4)	0.025 (9)*
C9	0.5674 (5)	0.27720 (15)	0.4819 (3)	0.0193 (6)
C10	0.6631 (5)	0.36864 (15)	0.6969 (3)	0.0209 (7)
C11	0.5912 (6)	0.42582 (16)	0.6492 (3)	0.0241 (7)
H11	0.668 (6)	0.4453 (15)	0.572 (3)	0.019 (8)*
C12	0.4053 (6)	0.45873 (17)	0.7111 (3)	0.0257 (7)
H12	0.354 (6)	0.4998 (16)	0.676 (4)	0.021 (9)*
C13	0.2881 (6)	0.43370 (17)	0.8217 (3)	0.0257 (7)
H13	0.159 (7)	0.4587 (17)	0.864 (4)	0.031 (10)*
C14	0.3598 (6)	0.37627 (17)	0.8703 (3)	0.0270 (7)
H14	0.286 (8)	0.3569 (19)	0.943 (4)	0.041 (11)*
C15	0.5472 (6)	0.34412 (17)	0.8103 (3)	0.0253 (7)
H15	0.589 (7)	0.3010 (19)	0.842 (4)	0.032 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0168 (11)	0.0391 (14)	0.0168 (11)	−0.0029 (10)	−0.0052 (9)	0.0048 (9)
O2	0.0156 (10)	0.0420 (14)	0.0200 (11)	−0.0051 (9)	−0.0028 (8)	0.0034 (10)
N1	0.0114 (11)	0.0413 (17)	0.0167 (13)	−0.0052 (11)	0.0007 (9)	−0.0008 (11)
N2	0.0141 (12)	0.0399 (17)	0.0133 (12)	−0.0030 (11)	−0.0017 (9)	0.0015 (11)
C1	0.0126 (13)	0.0320 (17)	0.0176 (14)	0.0016 (12)	0.0017 (11)	−0.0017 (12)
C2	0.0187 (15)	0.0354 (18)	0.0152 (14)	0.0005 (13)	−0.0026 (11)	−0.0017 (12)
C3	0.0230 (16)	0.0355 (19)	0.0185 (16)	0.0031 (13)	0.0024 (12)	0.0001 (13)
C4	0.0196 (15)	0.0359 (19)	0.0235 (17)	−0.0016 (14)	0.0066 (12)	0.0009 (14)
C5	0.0126 (13)	0.0367 (19)	0.0221 (16)	0.0002 (12)	0.0021 (11)	−0.0022 (13)
C6	0.0133 (13)	0.0322 (17)	0.0159 (14)	0.0024 (12)	0.0022 (10)	−0.0023 (12)
C7	0.0126 (13)	0.0355 (18)	0.0143 (14)	−0.0015 (12)	−0.0006 (11)	0.0006 (12)
C8	0.0147 (14)	0.0342 (18)	0.0150 (14)	−0.0014 (12)	0.0011 (11)	0.0018 (12)
C9	0.0120 (13)	0.0321 (17)	0.0136 (14)	0.0000 (11)	−0.0010 (10)	−0.0010 (11)
C10	0.0149 (14)	0.0347 (18)	0.0130 (13)	−0.0015 (12)	−0.0014 (10)	−0.0025 (12)
C11	0.0227 (15)	0.0329 (18)	0.0169 (15)	−0.0036 (13)	0.0018 (12)	−0.0001 (13)
C12	0.0229 (16)	0.0340 (19)	0.0203 (16)	−0.0002 (13)	0.0022 (12)	−0.0002 (13)
C13	0.0176 (15)	0.039 (2)	0.0207 (16)	0.0010 (13)	0.0008 (12)	−0.0034 (14)
C14	0.0243 (16)	0.038 (2)	0.0191 (16)	0.0009 (14)	0.0032 (12)	0.0017 (14)
C15	0.0205 (15)	0.038 (2)	0.0177 (15)	0.0005 (14)	−0.0002 (12)	0.0022 (13)

Geometric parameters (Å, º) top

O1—C8	1.415 (4)	C5—H5	1.03 (4)
O1—H1	0.84 (4)	C7—C10	1.517 (4)
O2—C9	1.228 (4)	C7—C8	1.544 (5)
N1—C6	1.383 (4)	C7—H7	1.00 (3)
N1—C7	1.444 (4)	C8—C9	1.512 (4)
N1—H1A	0.93 (5)	C8—H8	0.99 (4)
N2—C9	1.337 (4)	C10—C11	1.380 (5)
N2—C1	1.412 (4)	C10—C15	1.402 (4)
N2—H2A	0.88 (4)	C11—C12	1.394 (5)
C1—C2	1.403 (4)	C11—H11	0.98 (3)
C1—C6	1.409 (4)	C12—C13	1.387 (5)
C2—C3	1.366 (5)	C12—H12	0.99 (4)
C2—H2	0.91 (4)	C13—C14	1.387 (5)
C3—C4	1.394 (5)	C13—H13	0.99 (4)
C3—H3	0.94 (4)	C14—C15	1.384 (5)
C4—C5	1.376 (5)	C14—H14	0.93 (4)
C4—H4	0.93 (4)	C15—H15	1.01 (4)
C5—C6	1.407 (4)

C8—O1—H1	108 (3)	C10—C7—H7	106.8 (19)
C6—N1—C7	128.8 (3)	C8—C7—H7	106.3 (18)
C6—N1—H1A	113 (3)	O1—C8—C9	107.8 (2)
C7—N1—H1A	118 (3)	O1—C8—C7	111.1 (2)
C9—N2—C1	131.9 (3)	C9—C8—C7	112.3 (3)
C9—N2—H2A	111 (2)	O1—C8—H8	111 (2)
C1—N2—H2A	116 (2)	C9—C8—H8	107 (2)
C2—C1—C6	119.0 (3)	C7—C8—H8	108 (2)
C2—C1—N2	114.9 (3)	O2—C9—N2	122.3 (3)
C6—C1—N2	126.1 (3)	O2—C9—C8	119.1 (3)
C3—C2—C1	122.6 (3)	N2—C9—C8	118.6 (3)
C3—C2—H2	121 (2)	C11—C10—C15	118.8 (3)
C1—C2—H2	117 (2)	C11—C10—C7	122.3 (3)
C2—C3—C4	118.8 (3)	C15—C10—C7	118.9 (3)
C2—C3—H3	119 (2)	C10—C11—C12	121.1 (3)
C4—C3—H3	122 (3)	C10—C11—H11	122 (2)
C5—C4—C3	119.6 (3)	C12—C11—H11	117 (2)
C5—C4—H4	119 (2)	C13—C12—C11	119.9 (3)
C3—C4—H4	122 (2)	C13—C12—H12	119 (2)
C4—C5—C6	122.7 (3)	C11—C12—H12	121 (2)
C4—C5—H5	120 (2)	C12—C13—C14	119.3 (3)
C6—C5—H5	118 (2)	C12—C13—H13	118 (2)
N1—C6—C5	116.5 (3)	C14—C13—H13	123 (2)
N1—C6—C1	126.3 (3)	C15—C14—C13	120.7 (3)
C5—C6—C1	117.2 (3)	C15—C14—H14	116 (3)
N1—C7—C10	113.8 (3)	C13—C14—H14	123 (3)
N1—C7—C8	109.8 (2)	C14—C15—C10	120.2 (3)
C10—C7—C8	113.8 (2)	C14—C15—H15	120 (2)
N1—C7—H7	105.7 (19)	C10—C15—H15	120 (2)

C9—N2—C1—C2	155.0 (3)	C10—C7—C8—C9	47.4 (3)
C9—N2—C1—C6	−27.6 (5)	C1—N2—C9—O2	−176.8 (3)
C6—C1—C2—C3	0.5 (5)	C1—N2—C9—C8	4.0 (5)
N2—C1—C2—C3	178.1 (3)	O1—C8—C9—O2	0.4 (4)
C1—C2—C3—C4	0.4 (5)	C7—C8—C9—O2	−122.2 (3)
C2—C3—C4—C5	−0.9 (5)	O1—C8—C9—N2	179.6 (3)
C3—C4—C5—C6	0.7 (5)	C7—C8—C9—N2	57.0 (4)
C7—N1—C6—C5	177.8 (3)	N1—C7—C10—C11	10.6 (4)
C7—N1—C6—C1	−1.9 (5)	C8—C7—C10—C11	−116.2 (3)
C4—C5—C6—N1	−179.5 (3)	N1—C7—C10—C15	−167.2 (3)
C4—C5—C6—C1	0.2 (5)	C8—C7—C10—C15	66.0 (4)
C2—C1—C6—N1	178.9 (3)	C15—C10—C11—C12	−0.6 (5)
N2—C1—C6—N1	1.6 (5)	C7—C10—C11—C12	−178.3 (3)
C2—C1—C6—C5	−0.7 (4)	C10—C11—C12—C13	−0.7 (5)
N2—C1—C6—C5	−178.1 (3)	C11—C12—C13—C14	0.7 (5)
C6—N1—C7—C10	−83.5 (4)	C12—C13—C14—C15	0.4 (5)
C6—N1—C7—C8	45.3 (4)	C13—C14—C15—C10	−1.7 (5)
N1—C7—C8—O1	157.8 (2)	C11—C10—C15—C14	1.7 (5)
C10—C7—C8—O1	−73.4 (3)	C7—C10—C15—C14	179.5 (3)
N1—C7—C8—C9	−81.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (4)	2.01 (4)	2.556 (3)	122 (4)
N2—H2A···O1ⁱ	0.88 (4)	2.09 (4)	2.922 (3)	157 (3)
C8—H8···O2ⁱⁱ	0.99 (4)	2.57 (4)	3.395 (4)	141 (3)
C12—H12···Cg1ⁱⁱⁱ	0.99 (4)	2.85 (3)	3.696 (4)	144 (3)
N1—H1A···Cg2ⁱⁱ	0.99 (5)	2.63 (3)	3.457 (3)	149 (3)

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

Acknowledgements

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

References

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