1-(4-Bromo­benzo­yl)-2-phenyl­pyrrolidine-2-carboxamide

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

doi:10.1107/S1600536808003954

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o580

doi:10.1107/S1600536808003954

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1-(4-Bromobenzoyl)-2-phenylpyrrolidine-2-carboxamide

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

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

(Received 31 January 2008; accepted 6 February 2008; online 13 February 2008)

In the title compound, C₁₈H₁₇BrN₂O₂, which is a potential human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor, the pyrrolidine ring exhibits an envelope conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds [N⋯O = 2.861 (3) Å] link the molecules into centrosymmetric dimers.

Related literature

For related crystal structures, see: Karapetyan et al. (2002 ); Tamazyan et al. (2002 , 2007 ). For details of the synthesis, see: Martirosyan et al. (2000 , 2004 ). For potential pharmacological applications, see: De Clercq (1996 ).

Experimental

Crystal data

C₁₈H₁₇BrN₂O₂
M_r = 373.25
Monoclinic, P 2₁ /c
a = 9.5707 (19) Å
b = 13.738 (3) Å
c = 13.302 (3) Å
β = 96.99 (2)°
V = 1736.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 260 (2) K
0.14 mm (radius)

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: for a sphere (SHELXTL; Sheldrick, 2008 ) T_min = 0.612, T_max = 0.617
8356 measured reflections
4180 independent reflections
2941 reflections with I > 2σ(I)
R_int = 0.050
3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.118
S = 1.02
4180 reflections
216 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7b⋯O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a⋯O8ⁱ	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: DATACOL 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/S1600536808003954/cv2386sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003954/cv2386Isup2.hkl

checkCIF report

Comment top

The title compound, (I), belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs), which exhibit potential HIV-1 RT inhibition properties (De Clercq, 1996).

In (I) (Fig. 1), all bond lengths and angles are in good agreement with those observed in the related compounds (Karapetyan et al., 2002; Tamazyan et al., 2002, 2007). Both H atoms of amide group, H7b and H7a, respectively, are involved in intra- and intermolecular N—H···O hydrogen bonds (Table 1). The latter one links the molecules into centrosymmetric dimers (Fig. 2).

Related literature top

For related crystal structures, see: Karapetyan et al. (2002); Tamazyan et al. (2002, 2007). For details of the synthesis, see Martirosyan et al. (2000, 2004). For potential pharmacological applications, see De Clercq (1996).

Experimental top

The title compound was synthesized by cycloalkylation of N1-(3-chloropropyl)-N1-cyano(phenyl)methyl-4-bromobenzamide in phase transfer catalyses condition to 1-(4-bromobenzoyl)-2-phenyl-2-pyrrolidinecarbonitrile and then by hydrolizes with concentric sulfuric acid (Martirosyan et al., 2000, 2004). The compound as synthesized is a racemic mixture of optical isomers (R and S) of 1-(4-bromobenzoyl)-2-phenyl-2-pyrrolidinecarboxamide molecule. The crystals were grown from methanol solution. The suitable sample with spherical shape of the size ~0.28 mm was prepared and selected for X-ray diffraction experiment.

Computing details top

Data collection: DATACOL 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. The molecular structure of (I) showing the atomic numbering and displacement ellipsoids at the 50% probability level. H atoms omitted for clarity.
	Fig. 2. Hydrogen-bonded (dashed lines) dimer in the crystal structure of (I) [symmetry code: (i) -x, 1 - y, 1 - z]. Only H atoms participating in hydrogen-bonding are shown.

1-(4-Bromobenzoyl)-2-phenylpyrrolidine-2-carboxamide top

Crystal data top

C₁₈H₁₇BrN₂O₂	F(000) = 760
M_r = 373.25	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5707 (19) Å	θ = 13–16°
b = 13.738 (3) Å	µ = 2.38 mm⁻¹
c = 13.302 (3) Å	T = 260 K
β = 96.99 (2)°	Spherical, colourless
V = 1736.0 (6) Å³	0.28 × 0.28 × 0.28 × 0.14 (radius) mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2941 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
θ/2θ scans	h = −12→12
Absorption correction: for a sphere (SHELXTL; Sheldrick, 2008)	k = 0→18
T_min = 0.612, T_max = 0.617	l = −17→17
8356 measured reflections	3 standard reflections every 180 min
4180 independent reflections	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) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0458P)² + 1.2016P] where P = (F_o² + 2F_c²)/3
4180 reflections	(Δ/σ)_max = 0.001
216 parameters	Δρ_max = 0.87 e Å⁻³
10 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

C₁₈H₁₇BrN₂O₂	V = 1736.0 (6) Å³
M_r = 373.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5707 (19) Å	µ = 2.38 mm⁻¹
b = 13.738 (3) Å	T = 260 K
c = 13.302 (3) Å	0.28 × 0.28 × 0.28 × 0.14 (radius) mm
β = 96.99 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2941 reflections with I > 2σ(I)
Absorption correction: for a sphere (SHELXTL; Sheldrick, 2008)	R_int = 0.050
T_min = 0.612, T_max = 0.617	3 standard reflections every 180 min
8356 measured reflections	intensity decay: none
4180 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	10 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.87 e Å⁻³
4180 reflections	Δρ_min = −0.89 e Å⁻³
216 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
Br1	0.68968 (4)	1.01480 (3)	0.85408 (3)	0.07187 (17)
C1	−0.0555 (2)	0.71666 (16)	0.64026 (16)	0.0217 (4)
N2	0.08435 (19)	0.75423 (14)	0.68588 (13)	0.0230 (4)
C3	0.1138 (3)	0.7265 (2)	0.79443 (18)	0.0372 (6)
H3A	0.1112	0.7831	0.8379	0.045*
H3B	0.2051	0.6955	0.8084	0.045*
C4	−0.0033 (3)	0.65609 (19)	0.80987 (18)	0.0330 (5)
H4A	−0.0257	0.6581	0.8790	0.040*
H4B	0.0215	0.5900	0.7935	0.040*
C5	−0.1249 (3)	0.69388 (18)	0.73599 (17)	0.0277 (5)
H5A	−0.1656	0.7520	0.7620	0.033*
H5B	−0.1977	0.6449	0.7224	0.033*
C6	−0.0375 (2)	0.62094 (16)	0.58089 (16)	0.0225 (5)
N7	0.0475 (3)	0.62518 (17)	0.50977 (16)	0.0310 (5)
H7A	0.060 (3)	0.572 (2)	0.477 (2)	0.026 (7)*
H7B	0.089 (3)	0.677 (2)	0.502 (2)	0.038 (8)*
O8	−0.1011 (2)	0.54709 (12)	0.60012 (14)	0.0357 (4)
C9	−0.1430 (2)	0.78995 (16)	0.57304 (17)	0.0245 (5)
C10	−0.1242 (3)	0.88979 (18)	0.5831 (2)	0.0333 (5)
H10	−0.0515	0.9139	0.6291	0.040*
C11	−0.2120 (3)	0.9539 (2)	0.5257 (2)	0.0448 (7)
H11	−0.1975	1.0206	0.5328	0.054*
C12	−0.3217 (3)	0.9190 (2)	0.4578 (2)	0.0484 (8)
H12	−0.3811	0.9621	0.4193	0.058*
C13	−0.3422 (3)	0.8208 (2)	0.4475 (2)	0.0454 (7)
H13	−0.4160	0.7973	0.4021	0.055*
C14	−0.2534 (3)	0.75578 (19)	0.50447 (19)	0.0341 (6)
H14	−0.2680	0.6891	0.4966	0.041*
C15	0.1780 (2)	0.79997 (16)	0.63414 (17)	0.0244 (5)
O16	0.16487 (18)	0.80521 (12)	0.54045 (12)	0.0298 (4)
C17	0.3019 (2)	0.84793 (17)	0.69371 (18)	0.0264 (5)
C18	0.4350 (3)	0.8311 (2)	0.6659 (2)	0.0356 (6)
H18	0.4463	0.7867	0.6148	0.043*
C19	0.5505 (3)	0.8797 (2)	0.7137 (2)	0.0441 (7)
H19	0.6397	0.8679	0.6955	0.053*
C20	0.5317 (3)	0.9461 (2)	0.7890 (2)	0.0412 (7)
C21	0.4003 (3)	0.9652 (2)	0.8166 (2)	0.0410 (6)
H21	0.3892	1.0110	0.8666	0.049*
C22	0.2853 (3)	0.91537 (19)	0.7691 (2)	0.0337 (6)
H22	0.1962	0.9271	0.7877	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0470 (2)	0.0818 (3)	0.0793 (3)	−0.02922 (18)	−0.02262 (18)	0.0072 (2)
C1	0.0249 (10)	0.0220 (11)	0.0184 (10)	−0.0011 (8)	0.0038 (8)	−0.0017 (8)
N2	0.0263 (9)	0.0274 (10)	0.0154 (9)	−0.0030 (8)	0.0033 (7)	−0.0008 (7)
C3	0.0455 (15)	0.0498 (16)	0.0152 (11)	−0.0080 (12)	−0.0002 (10)	0.0018 (11)
C4	0.0441 (14)	0.0370 (14)	0.0188 (11)	−0.0031 (11)	0.0070 (10)	0.0039 (10)
C5	0.0329 (12)	0.0292 (12)	0.0229 (11)	0.0000 (10)	0.0108 (9)	−0.0012 (9)
C6	0.0273 (11)	0.0230 (11)	0.0170 (10)	0.0020 (9)	0.0014 (8)	0.0005 (8)
N7	0.0464 (13)	0.0213 (11)	0.0280 (11)	−0.0039 (10)	0.0159 (9)	−0.0048 (9)
O8	0.0492 (11)	0.0245 (9)	0.0365 (10)	−0.0080 (8)	0.0176 (8)	−0.0047 (7)
C9	0.0266 (11)	0.0263 (11)	0.0216 (11)	0.0033 (9)	0.0070 (9)	0.0019 (9)
C10	0.0359 (13)	0.0281 (13)	0.0367 (14)	0.0033 (10)	0.0076 (11)	0.0004 (11)
C11	0.0519 (17)	0.0289 (13)	0.0556 (19)	0.0102 (12)	0.0146 (15)	0.0123 (13)
C12	0.0484 (17)	0.0498 (18)	0.0472 (17)	0.0196 (14)	0.0065 (14)	0.0200 (14)
C13	0.0398 (15)	0.0563 (19)	0.0375 (16)	0.0111 (13)	−0.0064 (12)	0.0058 (13)
C14	0.0359 (13)	0.0332 (13)	0.0324 (13)	0.0040 (11)	0.0011 (11)	−0.0017 (11)
C15	0.0282 (11)	0.0221 (11)	0.0237 (11)	0.0022 (9)	0.0063 (9)	−0.0015 (9)
O16	0.0383 (9)	0.0314 (9)	0.0208 (8)	−0.0058 (7)	0.0078 (7)	−0.0010 (7)
C17	0.0257 (11)	0.0270 (11)	0.0267 (11)	0.0000 (9)	0.0042 (9)	0.0001 (10)
C18	0.0310 (13)	0.0372 (14)	0.0398 (15)	0.0024 (11)	0.0095 (11)	−0.0016 (11)
C19	0.0244 (12)	0.0528 (17)	0.0552 (18)	0.0022 (11)	0.0060 (12)	0.0068 (15)
C20	0.0299 (13)	0.0445 (15)	0.0453 (16)	−0.0118 (11)	−0.0107 (11)	0.0070 (13)
C21	0.0430 (15)	0.0394 (15)	0.0392 (15)	−0.0072 (12)	−0.0001 (12)	−0.0086 (12)
C22	0.0287 (12)	0.0357 (13)	0.0374 (14)	−0.0013 (10)	0.0064 (10)	−0.0093 (11)

Geometric parameters (Å, º) top

Br1—C20	1.899 (3)	C10—C11	1.382 (4)
C1—N2	1.493 (3)	C10—H10	0.9300
C1—C9	1.527 (3)	C11—C12	1.385 (5)
C1—C5	1.538 (3)	C11—H11	0.9300
C1—C6	1.554 (3)	C12—C13	1.368 (5)
N2—C15	1.350 (3)	C12—H12	0.9300
N2—C3	1.487 (3)	C13—C14	1.392 (4)
C3—C4	1.513 (4)	C13—H13	0.9300
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—O16	1.239 (3)
C4—C5	1.520 (3)	C15—C17	1.496 (3)
C4—H4A	0.9700	C17—C18	1.388 (3)
C4—H4B	0.9700	C17—C22	1.389 (3)
C5—H5A	0.9700	C18—C19	1.378 (4)
C5—H5B	0.9700	C18—H18	0.9300
C6—O8	1.226 (3)	C19—C20	1.383 (4)
C6—N7	1.321 (3)	C19—H19	0.9300
N7—H7A	0.86 (3)	C20—C21	1.378 (4)
N7—H7B	0.83 (3)	C21—C22	1.383 (4)
C9—C10	1.388 (3)	C21—H21	0.9300
C9—C14	1.391 (3)	C22—H22	0.9300

N2—C1—C9	114.23 (18)	C11—C10—C9	121.0 (3)
N2—C1—C5	100.93 (17)	C11—C10—H10	119.5
C9—C1—C5	110.99 (18)	C9—C10—H10	119.5
N2—C1—C6	110.43 (17)	C10—C11—C12	120.1 (3)
C9—C1—C6	110.32 (17)	C10—C11—H11	120.0
C5—C1—C6	109.54 (18)	C12—C11—H11	120.0
C15—N2—C3	123.7 (2)	C13—C12—C11	119.6 (3)
C15—N2—C1	124.89 (18)	C13—C12—H12	120.2
C3—N2—C1	111.14 (18)	C11—C12—H12	120.2
N2—C3—C4	103.87 (19)	C12—C13—C14	120.6 (3)
N2—C3—H3A	111.0	C12—C13—H13	119.7
C4—C3—H3A	111.0	C14—C13—H13	119.7
N2—C3—H3B	111.0	C9—C14—C13	120.3 (3)
C4—C3—H3B	111.0	C9—C14—H14	119.8
H3A—C3—H3B	109.0	C13—C14—H14	119.8
C3—C4—C5	102.4 (2)	O16—C15—N2	123.2 (2)
C3—C4—H4A	111.3	O16—C15—C17	118.9 (2)
C5—C4—H4A	111.3	N2—C15—C17	117.9 (2)
C3—C4—H4B	111.3	C18—C17—C22	119.5 (2)
C5—C4—H4B	111.3	C18—C17—C15	118.6 (2)
H4A—C4—H4B	109.2	C22—C17—C15	121.5 (2)
C4—C5—C1	103.39 (19)	C19—C18—C17	120.5 (3)
C4—C5—H5A	111.1	C19—C18—H18	119.8
C1—C5—H5A	111.1	C17—C18—H18	119.8
C4—C5—H5B	111.1	C18—C19—C20	119.1 (3)
C1—C5—H5B	111.1	C18—C19—H19	120.5
H5A—C5—H5B	109.1	C20—C19—H19	120.5
O8—C6—N7	123.4 (2)	C21—C20—C19	121.5 (2)
O8—C6—C1	120.3 (2)	C21—C20—Br1	119.0 (2)
N7—C6—C1	116.3 (2)	C19—C20—Br1	119.5 (2)
C6—N7—H7A	117.1 (18)	C20—C21—C22	119.0 (3)
C6—N7—H7B	119 (2)	C20—C21—H21	120.5
H7A—N7—H7B	124 (3)	C22—C21—H21	120.5
C10—C9—C14	118.4 (2)	C21—C22—C17	120.4 (2)
C10—C9—C1	122.7 (2)	C21—C22—H22	119.8
C14—C9—C1	118.7 (2)	C17—C22—H22	119.8

C9—C1—N2—C15	−49.1 (3)	C1—C9—C10—C11	−175.3 (2)
C5—C1—N2—C15	−168.3 (2)	C9—C10—C11—C12	0.7 (4)
C6—C1—N2—C15	75.9 (3)	C10—C11—C12—C13	−0.2 (5)
C9—C1—N2—C3	136.3 (2)	C11—C12—C13—C14	−0.3 (5)
C5—C1—N2—C3	17.2 (2)	C10—C9—C14—C13	0.1 (4)
C6—C1—N2—C3	−98.6 (2)	C1—C9—C14—C13	175.0 (2)
C15—N2—C3—C4	−165.7 (2)	C12—C13—C14—C9	0.3 (4)
C1—N2—C3—C4	9.0 (3)	C3—N2—C15—O16	164.8 (2)
N2—C3—C4—C5	−31.7 (3)	C1—N2—C15—O16	−9.1 (3)
C3—C4—C5—C1	43.1 (2)	C3—N2—C15—C17	−16.3 (3)
N2—C1—C5—C4	−36.6 (2)	C1—N2—C15—C17	169.74 (19)
C9—C1—C5—C4	−158.09 (19)	O16—C15—C17—C18	−48.8 (3)
C6—C1—C5—C4	79.8 (2)	N2—C15—C17—C18	132.3 (2)
N2—C1—C6—O8	125.4 (2)	O16—C15—C17—C22	125.0 (3)
C9—C1—C6—O8	−107.4 (2)	N2—C15—C17—C22	−53.9 (3)
C5—C1—C6—O8	15.1 (3)	C22—C17—C18—C19	1.0 (4)
N2—C1—C6—N7	−55.3 (3)	C15—C17—C18—C19	174.9 (2)
C9—C1—C6—N7	71.9 (3)	C17—C18—C19—C20	−0.6 (4)
C5—C1—C6—N7	−165.6 (2)	C18—C19—C20—C21	−0.5 (4)
N2—C1—C9—C10	−23.9 (3)	C18—C19—C20—Br1	−179.2 (2)
C5—C1—C9—C10	89.4 (3)	C19—C20—C21—C22	1.2 (4)
C6—C1—C9—C10	−149.0 (2)	Br1—C20—C21—C22	179.9 (2)
N2—C1—C9—C14	161.4 (2)	C20—C21—C22—C17	−0.8 (4)
C5—C1—C9—C14	−85.3 (3)	C18—C17—C22—C21	−0.3 (4)
C6—C1—C9—C14	36.3 (3)	C15—C17—C22—C21	−174.0 (2)
C14—C9—C10—C11	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7b···O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a···O8ⁱ	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇BrN₂O₂
M_r	373.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	260
a, b, c (Å)	9.5707 (19), 13.738 (3), 13.302 (3)
β (°)	96.99 (2)
V (Å³)	1736.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.28 × 0.28 × 0.28 × 0.14 (radius)

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	For a sphere (SHELXTL; Sheldrick, 2008)
T_min, T_max	0.612, 0.617
No. of measured, independent and observed [I > 2σ(I)] reflections	8356, 4180, 2941
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.02
No. of reflections	4180
No. of parameters	216
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.89

Computer programs: DATACOL 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
N7—H7b···O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a···O8ⁱ	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

This work was supported by the Armenian Science and Education Foundation (ANSEF) (grant No. PS-chemorg-907).

References

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