1-Methyl-3-(4-chloro­benzo­yl)imidazo[1,2-a]pyridin-1-ium-2-olate

Rybakov, V.B.; Babaev, E.V.

doi:10.1107/S1600536811039614

organic compounds

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Volume 67| Part 10| October 2011| Page o2814

https://doi.org/10.1107/S1600536811039614

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1-Methyl-3-(4-chlorobenzoyl)imidazo[1,2-a]pyridin-1-ium-2-olate

Victor B. Rybakov ^a ^* and Eugene V. Babaev ^a

^aDepartament of Chemistry, Moscow State University, 119992 Moscow, Russian Federation
^*Correspondence e-mail: rybakov20021@yandex.ru

(Received 12 September 2011; accepted 27 September 2011; online 30 September 2011)

In the molecule of the title compound, C₁₅H₁₁ClN₂O₂, the nine-membered heterobicycle is approximately planar [largest deviation from least-squares plane = 0.012 (2) Å] and forms a dihedral angle of 51.14 (8)° with the plane of the 4-chlorophenyl group. There is a non-classical intramolecular hydrogen bond between the pyridine α-H atom and the O atom of the benzoyl group. The crystal structure is stabilized by weak C—H⋯O and C—H⋯Cl interactions involving the `olate' O atom and the Cl atom attached to the benzoyl group as acceptors.

Related literature

For related structures, see: Friedman et al. (1978 ); Rybakov et al. (1999 , 2000a ,b , 2001 , 2002 ). For the synthesis of 1-methyl-2-oxo-2,3-dihydroimidazopyridinium perchlorate, see: Sych & Gorb (1976 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₅H₁₁ClN₂O₂
M_r = 286.71
Monoclinic, P 2₁ /c
a = 8.190 (8) Å
b = 13.914 (3) Å
c = 11.675 (4) Å
β = 102.38 (2)°
V = 1299.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 295 K
0.30 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
2675 measured reflections
2546 independent reflections
1486 reflections with I > 2σ(I)
R_int = 0.042
1 standard reflections every 200 reflections intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.107
S = 0.94
2546 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O30	0.93	2.30	2.863 (3)	119
C8—H8⋯O2ⁱ	0.93	2.47	3.291 (4)	148
C32—H32⋯Cl34ⁱⁱ	0.93	2.93	3.794 (3)	155
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811039614/yk2022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039614/yk2022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811039614/yk2022Isup3.cml

checkCIF report

Comment top

Early we described crystal structures of "pyridylglycine" I (Rybakov et al., 1999) (Fig. 1) and the product of its cyclocondensation – 2-oxoimidazo[1,2-a]pyridine II (Rybakov et al., 2000a) (Fig. 1). According to Sych & Gorb (1976), we have also performed selective N–methylation of II and investigated the molecular and crystal structures of the resulting salt III (Rybakov et al., 2000b) (Fig. 1). In the present paper we continue the sequence I-II-III and report the molecular structure of the acylated derivative of the compound III - the mesoionic 1-methyl-3-(p–chlorobenzoyl)imidazo[1,2-a] pyridinium-2-olate IV (Fig. 1). The acylation of III was performed by using of 4-chlorobenzoyl chloride in the presence of triethylamine leading to green crystals of the derivative IV with the 60% yield.

The molecular structure of the mesoionic compound IV (Fig. 2) displays some remarkable features early observed for analogous fused imidazopyridines (Friedman et al., 1978) and oxazolopyridines (Rybakov et al., 2001; Rybakov et al., 2002). In particular, in the moiety O10═ C30—C3—C2═O2 the bonds length C3—C30 and C2—C3 correspond to single bonds (~1.43 Å), whereas the bonds length C30═O30 and C2═ O2 (~1.23 Å) correspond to double bonds, thus displaying the unusual ylide-like pattern of the imidazolone fragment. On the other hand, the sequence C5═C6–C7═C8 displays alternation of the bonds length, thus corresponding to quasi-diene fragment of the pyridine ring. These facts seem to be common to the entire class of azolopyridinium-2-olates. The intramolecular interaction C5—H5···O30 with parameters H5···O30 = 2.296 Å, C5···O30 = 2.863 (3)Å and angle C5—H5···O30 = 118.83° (Table 1) is found. The molecules in crystal are linked by weak intermolecular interactions: C8—H8···O2ⁱ with parameters H8···O2ⁱ = 2.466 Å, C8···O2ⁱ = 3.291 (4)Å and angle C8—H8···O2ⁱ = 147.86°; C32—H32···Cl34ⁱⁱ with parameters H32···Cl34ⁱⁱ = 2.931 Å, C32···Cl34 = 3.794 (3)Å and angle C32—H32···Cl34ⁱⁱ = 154.93°. Symmetry codes: (i) -x, y + 1/2, -z + 1/2; (ii) -x + 1, y + 1/2, -z + 1/2.

Related literature top

For related structures, see: Friedman et al. (1978); Rybakov et al. (1999, 2000a,b, 2001, (2002). For the synthesis of 1-methyl-2-oxo-2,3-dihydroimidazopyridinium perchlorate, see: Sych & Gorb (1976). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

1-Methyl-2-oxo-2,3-dihydroimidazopyridinium perchlorate III was obtained as described by Sych & Gorb (1976) (Fig. 2). In order to obtain 1-methyl-3-(4-chlorobenzoyl)imidazo[1,2-a]pyridinium-2-olate IV, triethylamine (2.24 ml, 0.016 mol) was added slowly to the solution of 2.0 g (8 mmol) III in 10 ml of acetonitrile, and 1.4 g (8 mmol) of 4-chlorobenzoil chloride was added to the obtained mixture. The reaction flask was stirred at room temperature for 1 h and then kept overnight. The precipitate was filtered and recrystallized from isopropyl alcohol. The yield was 1.3 g (60%). M.p. 479–481 K. ¹H NMR spectra (DMSO-d₆, p.p.m.): 9.96 (d, 1H, 9-H), 7.85 (dd, 1H, 8-H), 7.68 (m, 2H, p-ClPh), 7.61 (d, 1H, 6-H), 7.44 (m, 2H, p-ClPh), 7.34 (dd, 1H, 7-H), 3.38 (s, 3H, 4-Me). The numbering of protons is given according to the atoms numbering on Fig. 1.

Structure description top

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4 Software (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Synthesis path for IV.
	Fig. 2. ORTEP-3 (Farrugia, 1997) plot of the molecule IV with the atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

1-Methyl-3-(4-chlorobenzoyl)imidazo[1,2-a]pyridin-1-ium-2-olate top

Crystal data top

C₁₅H₁₁ClN₂O₂	F(000) = 592
M_r = 286.71	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 479–481 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.190 (8) Å	Cell parameters from 25 reflections
b = 13.914 (3) Å	θ = 13.0–14.8°
c = 11.675 (4) Å	µ = 0.30 mm⁻¹
β = 102.38 (2)°	T = 295 K
V = 1299.5 (14) Å³	Prism, green
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.042
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.3°
Graphite monochromator	h = −10→9
non–profiled ω scans	k = 0→17
2675 measured reflections	l = 0→14
2546 independent reflections	1 standard reflections every 200 reflections
1486 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0433P)²] where P = (F_o² + 2F_c²)/3
2546 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₁ClN₂O₂	V = 1299.5 (14) Å³
M_r = 286.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.190 (8) Å	µ = 0.30 mm⁻¹
b = 13.914 (3) Å	T = 295 K
c = 11.675 (4) Å	0.30 × 0.30 × 0.30 mm
β = 102.38 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.042
2675 measured reflections	1 standard reflections every 200 reflections
2546 independent reflections	intensity decay: 2%
1486 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.94	Δρ_max = 0.15 e Å⁻³
2546 reflections	Δρ_min = −0.26 e Å⁻³
182 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.0863 (3)	0.54749 (15)	0.22101 (19)	0.0505 (6)
C2	0.1226 (3)	0.45544 (18)	0.1820 (2)	0.0449 (6)
O2	0.0815 (2)	0.38150 (13)	0.22548 (16)	0.0594 (5)
C3	0.2076 (3)	0.47398 (16)	0.0895 (2)	0.0424 (6)
N4	0.2102 (2)	0.57470 (13)	0.07555 (17)	0.0416 (5)
C5	0.2755 (3)	0.62878 (19)	−0.0013 (2)	0.0521 (7)
H5	0.3244	0.5997	−0.0574	0.063*
C6	0.2675 (4)	0.7264 (2)	0.0060 (3)	0.0646 (9)
H6	0.3118	0.7641	−0.0457	0.078*
C7	0.1947 (4)	0.7704 (2)	0.0887 (3)	0.0690 (9)
H7	0.1903	0.8371	0.0920	0.083*
C8	0.1292 (4)	0.71635 (19)	0.1653 (3)	0.0609 (8)
H8	0.0801	0.7453	0.2213	0.073*
C9	0.1377 (3)	0.61773 (18)	0.1577 (2)	0.0469 (6)
C11	−0.0063 (4)	0.5623 (2)	0.3124 (3)	0.0725 (9)
H11A	0.0696	0.5797	0.3840	0.109*
H11B	−0.0636	0.5041	0.3240	0.109*
H11C	−0.0863	0.6129	0.2895	0.109*
C30	0.2748 (3)	0.40950 (17)	0.0162 (2)	0.0459 (6)
O30	0.3115 (3)	0.43543 (13)	−0.07607 (15)	0.0659 (6)
C31	0.3064 (3)	0.30759 (17)	0.0552 (2)	0.0390 (6)
C32	0.3762 (3)	0.28280 (17)	0.1699 (2)	0.0451 (6)
H32	0.3955	0.3304	0.2271	0.054*
C33	0.4177 (3)	0.18918 (18)	0.2012 (2)	0.0463 (6)
H33	0.4654	0.1733	0.2785	0.056*
C34	0.3869 (3)	0.11962 (17)	0.1154 (2)	0.0450 (6)
Cl34	0.43791 (11)	0.00078 (5)	0.15427 (8)	0.0725 (3)
C35	0.3144 (3)	0.14142 (17)	0.0010 (2)	0.0478 (7)
H35	0.2914	0.0931	−0.0552	0.057*
C36	0.2766 (3)	0.23515 (18)	−0.0291 (2)	0.0460 (7)
H36	0.2305	0.2507	−0.1068	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0450 (14)	0.0641 (14)	0.0448 (14)	0.0060 (11)	0.0150 (12)	−0.0039 (12)
C2	0.0378 (16)	0.0555 (15)	0.0389 (15)	0.0004 (12)	0.0023 (13)	−0.0033 (13)
O2	0.0603 (13)	0.0647 (12)	0.0568 (13)	−0.0035 (10)	0.0208 (11)	0.0127 (10)
C3	0.0415 (15)	0.0452 (13)	0.0396 (15)	0.0000 (11)	0.0071 (13)	0.0030 (11)
N4	0.0339 (12)	0.0468 (11)	0.0409 (12)	0.0017 (9)	0.0012 (10)	0.0011 (10)
C5	0.0418 (17)	0.0627 (17)	0.0506 (17)	0.0017 (13)	0.0071 (14)	0.0112 (14)
C6	0.050 (2)	0.0561 (17)	0.082 (2)	−0.0012 (14)	0.0015 (18)	0.0165 (16)
C7	0.056 (2)	0.0515 (17)	0.089 (3)	0.0079 (15)	−0.0079 (19)	−0.0010 (18)
C8	0.0476 (19)	0.0582 (17)	0.072 (2)	0.0084 (14)	0.0022 (17)	−0.0111 (16)
C9	0.0372 (16)	0.0568 (15)	0.0460 (17)	0.0101 (12)	0.0071 (13)	−0.0063 (13)
C11	0.069 (2)	0.098 (2)	0.057 (2)	0.0132 (18)	0.0286 (18)	−0.0073 (18)
C30	0.0430 (16)	0.0554 (16)	0.0382 (16)	−0.0002 (12)	0.0060 (13)	0.0004 (12)
O30	0.0985 (17)	0.0675 (12)	0.0383 (11)	0.0132 (11)	0.0289 (12)	0.0086 (10)
C31	0.0336 (14)	0.0519 (14)	0.0291 (14)	0.0011 (11)	0.0012 (11)	−0.0001 (11)
C32	0.0471 (17)	0.0500 (14)	0.0359 (15)	−0.0021 (12)	0.0037 (13)	−0.0056 (12)
C33	0.0409 (16)	0.0557 (15)	0.0392 (15)	0.0044 (12)	0.0019 (12)	0.0035 (13)
C34	0.0362 (15)	0.0475 (14)	0.0536 (17)	0.0070 (11)	0.0149 (14)	0.0050 (13)
Cl34	0.0791 (6)	0.0543 (4)	0.0870 (7)	0.0176 (4)	0.0246 (5)	0.0101 (4)
C35	0.0469 (17)	0.0510 (15)	0.0434 (16)	0.0013 (12)	0.0055 (13)	−0.0132 (13)
C36	0.0412 (16)	0.0596 (16)	0.0343 (15)	0.0038 (12)	0.0016 (13)	−0.0043 (12)

Geometric parameters (Å, º) top

Cl34—C34	1.742 (2)	C5—H5	0.9300
N4—C5	1.365 (3)	C30—O30	1.233 (3)
N4—C9	1.370 (3)	C30—C31	1.495 (3)
N4—C3	1.412 (3)	C31—C32	1.382 (3)
C2—C3	1.428 (3)	C31—C36	1.393 (3)
C3—C30	1.429 (3)	C32—C33	1.376 (3)
C2—O2	1.226 (3)	C32—H32	0.9300
C2—N1	1.412 (3)	C33—C34	1.377 (3)
N1—C9	1.346 (3)	C33—H33	0.9300
N1—C11	1.450 (3)	C34—C35	1.374 (3)
C9—C8	1.378 (3)	C35—C36	1.369 (3)
C8—C7	1.364 (4)	C35—H35	0.9300
C8—H8	0.9300	C36—H36	0.9300
C7—C6	1.382 (4)	C11—H11A	0.9600
C7—H7	0.9300	C11—H11B	0.9600
C6—C5	1.364 (4)	C11—H11C	0.9600
C6—H6	0.9300

C5—N4—C9	120.6 (2)	O30—C30—C3	122.5 (2)
C5—N4—C3	129.8 (2)	O30—C30—C31	119.0 (2)
C9—N4—C3	109.5 (2)	C3—C30—C31	118.5 (2)
N4—C3—C2	106.7 (2)	C32—C31—C36	118.5 (2)
N4—C3—C30	122.5 (2)	C32—C31—C30	122.7 (2)
C2—C3—C30	130.7 (2)	C36—C31—C30	118.6 (2)
O2—C2—N1	122.1 (2)	C33—C32—C31	121.4 (2)
O2—C2—C3	133.4 (2)	C33—C32—H32	119.3
N1—C2—C3	104.5 (2)	C31—C32—H32	119.3
C9—N1—C2	111.7 (2)	C32—C33—C34	118.4 (2)
C9—N1—C11	125.1 (2)	C32—C33—H33	120.8
C2—N1—C11	123.1 (2)	C34—C33—H33	120.8
N1—C9—N4	107.5 (2)	C35—C34—C33	121.7 (2)
N1—C9—C8	131.5 (3)	C35—C34—Cl34	119.5 (2)
N4—C9—C8	121.0 (3)	C33—C34—Cl34	118.8 (2)
C7—C8—C9	118.4 (3)	C36—C35—C34	119.1 (2)
C7—C8—H8	120.8	C36—C35—H35	120.4
C9—C8—H8	120.8	C34—C35—H35	120.4
C8—C7—C6	120.2 (3)	C35—C36—C31	120.8 (2)
C8—C7—H7	119.9	C35—C36—H36	119.6
C6—C7—H7	119.9	C31—C36—H36	119.6
C5—C6—C7	121.3 (3)	N1—C11—H11A	109.5
C5—C6—H6	119.4	N1—C11—H11B	109.5
C7—C6—H6	119.4	N1—C11—H11C	109.5
C6—C5—N4	118.5 (3)	H11A—C11—H11B	109.5
C6—C5—H5	120.7	H11A—C11—H11C	109.5
N4—C5—H5	120.7	H11B—C11—H11C	109.5

C5—N4—C3—C2	−179.6 (2)	C8—C7—C6—C5	0.1 (5)
C9—N4—C3—C2	2.5 (3)	C7—C6—C5—N4	−0.2 (4)
C5—N4—C3—C30	−2.0 (4)	C9—N4—C5—C6	0.3 (4)
C9—N4—C3—C30	−179.9 (2)	C3—N4—C5—C6	−177.5 (2)
N4—C3—C2—O2	176.9 (3)	N4—C3—C30—O30	−13.5 (4)
C30—C3—C2—O2	−0.5 (5)	C2—C3—C30—O30	163.5 (3)
N4—C3—C2—N1	−2.5 (3)	N4—C3—C30—C31	164.6 (2)
C30—C3—C2—N1	−179.8 (3)	C2—C3—C30—C31	−18.4 (4)
O2—C2—N1—C9	−177.7 (2)	O30—C30—C31—C32	136.1 (3)
C3—C2—N1—C9	1.8 (3)	C3—C30—C31—C32	−42.1 (4)
O2—C2—N1—C11	−2.0 (4)	O30—C30—C31—C36	−38.7 (4)
C3—C2—N1—C11	177.5 (2)	C3—C30—C31—C36	143.1 (2)
C2—N1—C9—N4	−0.3 (3)	C36—C31—C32—C33	0.7 (4)
C11—N1—C9—N4	−175.9 (2)	C30—C31—C32—C33	−174.1 (2)
C2—N1—C9—C8	−179.5 (3)	C31—C32—C33—C34	−0.5 (4)
C11—N1—C9—C8	4.9 (5)	C32—C33—C34—C35	−0.9 (4)
C5—N4—C9—N1	−179.5 (2)	C32—C33—C34—Cl34	−179.66 (19)
C3—N4—C9—N1	−1.4 (3)	C33—C34—C35—C36	2.0 (4)
C5—N4—C9—C8	−0.2 (4)	Cl34—C34—C35—C36	−179.18 (19)
C3—N4—C9—C8	177.9 (3)	C34—C35—C36—C31	−1.8 (4)
N1—C9—C8—C7	179.3 (3)	C32—C31—C36—C35	0.5 (4)
N4—C9—C8—C7	0.1 (4)	C30—C31—C36—C35	175.5 (2)
C9—C8—C7—C6	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O30	0.93	2.30	2.863 (3)	119
C8—H8···O2ⁱ	0.93	2.47	3.291 (4)	148
C32—H32···Cl34ⁱⁱ	0.93	2.93	3.794 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClN₂O₂
M_r	286.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.190 (8), 13.914 (3), 11.675 (4)
β (°)	102.38 (2)
V (Å³)	1299.5 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2675, 2546, 1486
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.107, 0.94
No. of reflections	2546
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O30	0.93	2.296	2.863 (3)	118.83
C8—H8···O2ⁱ	0.93	2.466	3.291 (4)	147.86
C32—H32···Cl34ⁱⁱ	0.93	2.931	3.794 (3)	154.93

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

Acknowledgements

The authors are indebted to I. V. Dlinnykh for the preparation of title compound. The authors wish to thank Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database ver. 5.32 (Allen, 2002).

References

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