7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexa­hydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

Tamazyan, R.; Ayvazyan, A.; Martirosyan, A.; Harutyunyan, G.; Martirosyan, V.

doi:10.1107/S160053680800408X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o587

doi:10.1107/S160053680800408X

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7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

Rafael Tamazyan,^a ^* Armen Ayvazyan,^a Ashot Martirosyan,^b Gohar Harutyunyan ^b and Vahan Martirosyan ^b

^aMolecular Structure Research Center, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia, and ^bInstitute of Fine Organic Chemistry, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia
^*Correspondence e-mail: rafael@msrc.am

(Received 29 January 2008; accepted 8 February 2008; online 13 February 2008)

The title compound, C₁₈H₁₅ClN₂O₂, is a potential human immunodeficiency virus type-1 (HIV-1) non-nucleoside reverse transcriptase inhibitor. The pyrrolidine ring adopts an envelope and the diazepine ring a boat conformation. In the crystal structure, two isomers (R and S) form centrosymmetric dimers via N—H⋯O hydrogen bonds.

Related literature

For details of the pharmacological properties of this family of compounds, see: De Clercq (1996 ). For the crystal structures of some analogues of the title compound, see: Karapetyan et al. (2002 ); Tamazyan et al. (2002 , 2007 ). For reference structural data, see Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₅ClN₂O₂
M_r = 326.77
Triclinic, $[P \overline 1]$
a = 8.9749 (18) Å
b = 9.2184 (18) Å
c = 9.912 (2) Å
α = 86.90 (3)°
β = 71.35 (3)°
γ = 88.27 (3)°
V = 775.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 (2) K
0.35 × 0.32 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
7347 measured reflections
4514 independent reflections
3148 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
4514 reflections
268 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O12ⁱ	0.85 (2)	2.35 (2)	2.997 (2)	133 (2)
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: DATCOL in CAD-4 (Enraf–Nonius, 1988 ); cell refinement: LS in CAD-4; data reduction: HELENA (Spek, 1997 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800408X/sj2462sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800408X/sj2462Isup2.hkl

checkCIF report

Comment top

Interest in X-ray structural investigation of title compound, (I), Fig. 1, is stimulated by its potentially HIV-1 RT inhibition properties. These compounds belong to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs).

All intramolecular interatomic distances in molecule are in good agreement with their mean statistical values (Allen et al., 1987). In the crystal structure dimers are formed by (R and S) optical isomers of molecules of (I) via O12···H4ⁱ—N4ⁱ and O12ⁱ···H4—N4 double hydrogen bonding (Table 1, Fig.2).

Related literature top

For details of the pharmacological properties of this family of compounds, see: De Clercq (1996). For the crystal structures of some analogues of the title compound, see: Karapetyan et al. (2002); Tamazyan et al. (2002, 2007). For reference structural data, see Allen et al. (1987).

Experimental top

A solution of 2-phenyl-2-pyrrolidinecarboxylic acid (0.01 mol) and 6-chloro-1,4-dihydro-2H-3,1-benzoxazine-2,4-dione (0.01 mol) in dry DMF (5 ml) was boiled for 4 h. After cooling in an ice bath the title compound formed as a colourless precipitate and was separated by filtration and washed with ethylacetate. The compound as synthesized was a racemic mixture. Crystals were grown from an ethanol solution of the compound.

Computing details top

Data collection: DATCOL in CAD-4 (Enraf–Nonius, 1988); cell refinement: LS in CAD-4 (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
	Fig. 2. The formation dimers of molecules via hydrogen bonding. For clarity only those H atoms participating in hydrogen bonding are depicted. Symmetry code: (i) 2 - x, -y, 2 - z

7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexahydro-1H- pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione top

Crystal data top

C₁₈H₁₅ClN₂O₂	Z = 2
M_r = 326.77	F(000) = 340
Triclinic, P1	D_x = 1.399 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9749 (18) Å	Cell parameters from 22 reflections
b = 9.2184 (18) Å	θ = 12.6–16.6°
c = 9.912 (2) Å	µ = 0.26 mm⁻¹
α = 86.90 (3)°	T = 293 K
β = 71.35 (3)°	Prism, colourless
γ = 88.27 (3)°	0.35 × 0.32 × 0.28 mm
V = 775.8 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.035
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.2°
Graphite monochromator	h = −12→12
θ/2θ scans	k = −12→12
7347 measured reflections	l = −13→13
4514 independent reflections	3 standard reflections every 180 min
3148 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.121	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0496P)² + 0.2193P] where P = (F_o² + 2F_c²)/3
4514 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₈H₁₅ClN₂O₂	γ = 88.27 (3)°
M_r = 326.77	V = 775.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.9749 (18) Å	Mo Kα radiation
b = 9.2184 (18) Å	µ = 0.26 mm⁻¹
c = 9.912 (2) Å	T = 293 K
α = 86.90 (3)°	0.35 × 0.32 × 0.28 mm
β = 71.35 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.035
7347 measured reflections	3 standard reflections every 180 min
4514 independent reflections	intensity decay: none
3148 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	All H-atom parameters refined
S = 1.02	Δρ_max = 0.27 e Å⁻³
4514 reflections	Δρ_min = −0.31 e Å⁻³
268 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C2	0.70626 (17)	0.27403 (17)	1.00932 (16)	0.0333 (3)
C3	0.66409 (19)	0.11255 (18)	1.04089 (17)	0.0389 (3)
C5	0.91077 (18)	0.04305 (16)	0.85230 (16)	0.0343 (3)
C6	0.9468 (2)	−0.05252 (19)	0.74145 (19)	0.0432 (4)
C7	1.0802 (2)	−0.0350 (2)	0.6255 (2)	0.0488 (4)
C8	1.1788 (2)	0.0798 (2)	0.61835 (19)	0.0470 (4)
C9	1.1492 (2)	0.1717 (2)	0.72885 (19)	0.0418 (4)
C10	1.01455 (17)	0.15430 (16)	0.84775 (16)	0.0332 (3)
C11	0.99809 (17)	0.25083 (15)	0.96767 (16)	0.0319 (3)
C14	0.8259 (2)	0.37447 (19)	1.17444 (18)	0.0391 (3)
C15	0.6494 (2)	0.3646 (2)	1.24567 (19)	0.0493 (4)
C16	0.5879 (2)	0.3677 (2)	1.11921 (19)	0.0448 (4)
C17	0.71935 (17)	0.32632 (16)	0.85722 (16)	0.0335 (3)
C18	0.8016 (2)	0.45256 (19)	0.79868 (18)	0.0405 (4)
C19	0.8104 (2)	0.5045 (2)	0.6632 (2)	0.0519 (4)
C20	0.7365 (3)	0.4332 (2)	0.5842 (2)	0.0571 (5)
C21	0.6523 (3)	0.3101 (2)	0.6421 (2)	0.0562 (5)
C22	0.6436 (2)	0.2556 (2)	0.7781 (2)	0.0439 (4)
Cl	1.33908 (7)	0.10803 (8)	0.46554 (6)	0.0735 (2)
H4	0.745 (2)	−0.072 (2)	0.987 (2)	0.052 (6)*
H6	0.874 (2)	−0.135 (2)	0.747 (2)	0.047 (5)*
H7	1.101 (3)	−0.097 (2)	0.551 (2)	0.062 (6)*
H9	1.219 (2)	0.246 (2)	0.725 (2)	0.049 (5)*
H18	0.851 (2)	0.504 (2)	0.853 (2)	0.048 (5)*
H19	0.864 (3)	0.590 (3)	0.625 (2)	0.065 (7)*
H20	0.745 (3)	0.481 (2)	0.482 (3)	0.064 (6)*
H21	0.599 (3)	0.259 (2)	0.595 (2)	0.058 (6)*
H22	0.584 (2)	0.174 (2)	0.816 (2)	0.051 (6)*
H14A	0.856 (2)	0.473 (2)	1.1500 (19)	0.040 (5)*
H15A	0.608 (3)	0.445 (3)	1.311 (2)	0.065 (6)*
H16A	0.596 (2)	0.467 (2)	1.080 (2)	0.052 (6)*
H14B	0.886 (2)	0.328 (2)	1.233 (2)	0.048 (5)*
H15B	0.623 (2)	0.270 (2)	1.301 (2)	0.054 (6)*
H16B	0.484 (3)	0.331 (2)	1.139 (2)	0.055 (6)*
N1	0.85316 (15)	0.29356 (14)	1.04452 (13)	0.0327 (3)
N4	0.77286 (16)	0.01605 (16)	0.96731 (15)	0.0390 (3)
O12	1.11592 (13)	0.28878 (12)	0.99545 (13)	0.0410 (3)
O13	0.54222 (16)	0.07208 (16)	1.12946 (15)	0.0604 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0302 (7)	0.0378 (8)	0.0323 (7)	−0.0007 (6)	−0.0102 (5)	−0.0035 (6)
C3	0.0373 (8)	0.0440 (9)	0.0352 (8)	−0.0102 (6)	−0.0106 (6)	−0.0001 (6)
C5	0.0389 (8)	0.0298 (7)	0.0351 (7)	0.0016 (6)	−0.0134 (6)	0.0008 (6)
C6	0.0543 (10)	0.0354 (8)	0.0433 (9)	0.0004 (7)	−0.0199 (8)	−0.0040 (7)
C7	0.0610 (11)	0.0468 (10)	0.0399 (9)	0.0125 (8)	−0.0178 (8)	−0.0093 (8)
C8	0.0423 (9)	0.0553 (11)	0.0373 (8)	0.0095 (8)	−0.0055 (7)	0.0000 (8)
C9	0.0352 (8)	0.0438 (9)	0.0437 (9)	0.0006 (7)	−0.0092 (7)	0.0006 (7)
C10	0.0324 (7)	0.0316 (7)	0.0359 (7)	0.0017 (5)	−0.0118 (6)	−0.0001 (6)
C11	0.0342 (7)	0.0263 (7)	0.0361 (7)	−0.0030 (5)	−0.0131 (6)	0.0040 (5)
C14	0.0480 (9)	0.0360 (8)	0.0367 (8)	0.0009 (7)	−0.0174 (7)	−0.0070 (7)
C15	0.0494 (10)	0.0602 (12)	0.0365 (9)	0.0050 (9)	−0.0102 (7)	−0.0112 (8)
C16	0.0394 (9)	0.0540 (11)	0.0407 (9)	0.0087 (8)	−0.0115 (7)	−0.0118 (8)
C17	0.0310 (7)	0.0363 (8)	0.0343 (7)	0.0047 (6)	−0.0119 (6)	−0.0050 (6)
C18	0.0417 (9)	0.0405 (9)	0.0418 (9)	−0.0001 (7)	−0.0168 (7)	−0.0032 (7)
C19	0.0563 (11)	0.0507 (11)	0.0463 (10)	−0.0007 (9)	−0.0147 (8)	0.0080 (8)
C20	0.0711 (13)	0.0641 (13)	0.0382 (9)	0.0087 (10)	−0.0213 (9)	−0.0014 (9)
C21	0.0687 (13)	0.0618 (12)	0.0508 (11)	0.0060 (10)	−0.0354 (10)	−0.0148 (9)
C22	0.0462 (9)	0.0440 (9)	0.0467 (9)	−0.0005 (7)	−0.0215 (8)	−0.0068 (8)
Cl	0.0554 (3)	0.0986 (5)	0.0498 (3)	0.0051 (3)	0.0065 (2)	−0.0053 (3)
N1	0.0349 (6)	0.0337 (6)	0.0318 (6)	−0.0002 (5)	−0.0134 (5)	−0.0037 (5)
N4	0.0418 (7)	0.0314 (7)	0.0417 (7)	−0.0078 (5)	−0.0106 (6)	0.0026 (6)
O12	0.0371 (6)	0.0362 (6)	0.0532 (7)	−0.0047 (4)	−0.0189 (5)	−0.0019 (5)
O13	0.0519 (8)	0.0631 (9)	0.0522 (8)	−0.0217 (7)	0.0050 (6)	−0.0049 (6)

Geometric parameters (Å, º) top

C2—N1	1.4858 (19)	C14—C15	1.517 (3)
C2—C17	1.527 (2)	C14—H14A	0.956 (19)
C2—C3	1.538 (2)	C14—H14B	0.99 (2)
C2—C16	1.539 (2)	C15—C16	1.522 (3)
C3—O13	1.217 (2)	C15—H15A	0.99 (2)
C3—N4	1.356 (2)	C15—H15B	1.00 (2)
C5—C10	1.395 (2)	C16—H16A	0.97 (2)
C5—C6	1.396 (2)	C16—H16B	0.96 (2)
C5—N4	1.407 (2)	C17—C22	1.387 (2)
C6—C7	1.375 (3)	C17—C18	1.393 (2)
C6—H6	1.010 (19)	C18—C19	1.380 (3)
C7—C8	1.385 (3)	C18—H18	0.95 (2)
C7—H7	0.93 (2)	C19—C20	1.378 (3)
C8—C9	1.374 (3)	C19—H19	0.94 (2)
C8—Cl	1.7370 (19)	C20—C21	1.376 (3)
C9—C10	1.398 (2)	C20—H20	1.06 (2)
C9—H9	0.93 (2)	C21—C22	1.392 (3)
C10—C11	1.490 (2)	C21—H21	0.92 (2)
C11—O12	1.2391 (18)	C22—H22	0.92 (2)
C11—N1	1.340 (2)	N4—H4	0.85 (2)
C14—N1	1.472 (2)

N1—C2—C17	113.17 (12)	C14—C15—C16	102.64 (15)
N1—C2—C3	106.65 (12)	C14—C15—H15A	111.5 (13)
C17—C2—C3	113.09 (13)	C16—C15—H15A	113.8 (13)
N1—C2—C16	101.84 (12)	C14—C15—H15B	110.0 (12)
C17—C2—C16	111.26 (13)	C16—C15—H15B	109.7 (12)
C3—C2—C16	110.18 (14)	H15A—C15—H15B	109.1 (18)
O13—C3—N4	121.24 (16)	C15—C16—C2	104.63 (14)
O13—C3—C2	122.47 (16)	C15—C16—H16A	107.3 (12)
N4—C3—C2	116.26 (13)	C2—C16—H16A	107.6 (12)
C10—C5—C6	119.46 (15)	C15—C16—H16B	115.7 (13)
C10—C5—N4	123.50 (14)	C2—C16—H16B	109.7 (13)
C6—C5—N4	116.96 (15)	H16A—C16—H16B	111.4 (18)
C7—C6—C5	120.84 (17)	C22—C17—C18	118.84 (15)
C7—C6—H6	119.9 (11)	C22—C17—C2	121.50 (15)
C5—C6—H6	119.3 (11)	C18—C17—C2	119.56 (14)
C6—C7—C8	119.40 (17)	C19—C18—C17	120.52 (17)
C6—C7—H7	120.2 (14)	C19—C18—H18	119.7 (12)
C8—C7—H7	120.4 (14)	C17—C18—H18	119.8 (12)
C9—C8—C7	120.77 (17)	C20—C19—C18	120.54 (19)
C9—C8—Cl	120.40 (15)	C20—C19—H19	119.1 (14)
C7—C8—Cl	118.82 (15)	C18—C19—H19	120.3 (14)
C8—C9—C10	120.23 (17)	C21—C20—C19	119.41 (18)
C8—C9—H9	120.2 (12)	C21—C20—H20	124.0 (12)
C10—C9—H9	119.6 (12)	C19—C20—H20	116.5 (12)
C5—C10—C9	119.18 (15)	C20—C21—C22	120.71 (19)
C5—C10—C11	123.97 (14)	C20—C21—H21	123.0 (13)
C9—C10—C11	116.69 (14)	C22—C21—H21	116.3 (14)
O12—C11—N1	121.43 (14)	C17—C22—C21	119.96 (18)
O12—C11—C10	120.38 (14)	C17—C22—H22	120.9 (13)
N1—C11—C10	118.18 (13)	C21—C22—H22	119.1 (13)
N1—C14—C15	103.15 (14)	C11—N1—C14	121.27 (13)
N1—C14—H14A	110.2 (11)	C11—N1—C2	126.30 (12)
C15—C14—H14A	110.6 (11)	C14—N1—C2	112.36 (12)
N1—C14—H14B	109.6 (11)	C3—N4—C5	128.71 (14)
C15—C14—H14B	112.6 (11)	C3—N4—H4	113.7 (14)
H14A—C14—H14B	110.4 (15)	C5—N4—H4	116.9 (14)

N1—C2—C3—O13	118.43 (17)	C3—C2—C17—C22	23.3 (2)
C17—C2—C3—O13	−116.54 (18)	C16—C2—C17—C22	−101.29 (18)
C16—C2—C3—O13	8.7 (2)	N1—C2—C17—C18	−38.96 (19)
N1—C2—C3—N4	−59.63 (17)	C3—C2—C17—C18	−160.38 (14)
C17—C2—C3—N4	65.40 (18)	C16—C2—C17—C18	75.00 (18)
C16—C2—C3—N4	−169.39 (14)	C22—C17—C18—C19	−1.4 (2)
C10—C5—C6—C7	−2.5 (2)	C2—C17—C18—C19	−177.78 (16)
N4—C5—C6—C7	−179.40 (15)	C17—C18—C19—C20	0.7 (3)
C5—C6—C7—C8	−0.6 (3)	C18—C19—C20—C21	0.6 (3)
C6—C7—C8—C9	3.3 (3)	C19—C20—C21—C22	−1.2 (3)
C6—C7—C8—Cl	−175.46 (14)	C18—C17—C22—C21	0.8 (3)
C7—C8—C9—C10	−2.9 (3)	C2—C17—C22—C21	177.10 (16)
Cl—C8—C9—C10	175.88 (13)	C20—C21—C22—C17	0.5 (3)
C6—C5—C10—C9	2.9 (2)	O12—C11—N1—C14	−6.6 (2)
N4—C5—C10—C9	179.60 (14)	C10—C11—N1—C14	172.75 (13)
C6—C5—C10—C11	−172.22 (14)	O12—C11—N1—C2	170.27 (13)
N4—C5—C10—C11	4.5 (2)	C10—C11—N1—C2	−10.4 (2)
C8—C9—C10—C5	−0.3 (2)	C15—C14—N1—C11	−165.56 (14)
C8—C9—C10—C11	175.20 (15)	C15—C14—N1—C2	17.18 (18)
C5—C10—C11—O12	141.38 (15)	C17—C2—N1—C11	−50.6 (2)
C9—C10—C11—O12	−33.9 (2)	C3—C2—N1—C11	74.38 (18)
C5—C10—C11—N1	−38.0 (2)	C16—C2—N1—C11	−170.11 (15)
C9—C10—C11—N1	146.80 (14)	C17—C2—N1—C14	126.50 (14)
N1—C14—C15—C16	−34.22 (19)	C3—C2—N1—C14	−108.52 (14)
C14—C15—C16—C2	39.5 (2)	C16—C2—N1—C14	6.98 (17)
N1—C2—C16—C15	−28.50 (18)	O13—C3—N4—C5	172.76 (16)
C17—C2—C16—C15	−149.37 (15)	C2—C3—N4—C5	−9.1 (2)
C3—C2—C16—C15	84.38 (18)	C10—C5—N4—C3	43.9 (2)
N1—C2—C17—C22	144.75 (15)	C6—C5—N4—C3	−139.36 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O12ⁱ	0.85 (2)	2.35 (2)	2.997 (2)	133 (2)

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClN₂O₂
M_r	326.77
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9749 (18), 9.2184 (18), 9.912 (2)
α, β, γ (°)	86.90 (3), 71.35 (3), 88.27 (3)
V (Å³)	775.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.32 × 0.28

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7347, 4514, 3148
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.02
No. of reflections	4514
No. of parameters	268
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31

Computer programs: DATCOL in CAD-4 (Enraf–Nonius, 1988), LS in CAD-4 (Enraf–Nonius, 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O12ⁱ	0.85 (2)	2.35 (2)	2.997 (2)	133 (2)

Symmetry code: (i) −x+2, −y, −z+2.

Acknowledgements

This research was carried out under the framework of the Armenian Science and Education Foundation (ANSEF grant No. PS-chemorg-907). The authors express their thanks to ANSEF.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
De Clercq, E. (1996). Rev. Med. Virol. 6, 97–117. CrossRef PubMed CAS Web of Science Google Scholar
Enraf–Nonius (1988). CAD-4 Manual. Version 5.0. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Karapetyan, H., Tamazyan, R., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o399–o401. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (1997). HELENA. University of Utrecht, The Netherlands. Google Scholar
Tamazyan, R., Ayvazyan, A., Martirosyan, A., Martirosyan, V. & Schinazi, R. (2007). Acta Cryst. E63, o3967. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tamazyan, R., Karapetyan, H., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o386–o388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 3| March 2008| Page o587

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

7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexa­hydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione