(3RS)-S-[1-(3-Chloro­phen­yl)-2-oxopyr­roli­din-3-yl]thio­uronium bromide

Hanusek, J.; Sedlák, M.; Drabina, P.; Ružička, A.

doi:10.1107/S1600536809001603

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o411-o412

doi:10.1107/S1600536809001603

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(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]thiouronium bromide

Jiří Hanusek,^a ^* Miloš Sedlák,^a Pavel Drabina ^a and Aleš Ružička ^b

^aInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, nám. Čs. legií 565, Pardubice 532 10, Czech Republic, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, nám. Čs. legií 565, Pardubice 532 10, Czech Republic
^*Correspondence e-mail: jiri.hanusek@upce.cz

(Received 16 October 2008; accepted 13 January 2009; online 28 January 2009)

In the title molecular salt, C₁₁H₁₃ClN₃OS⁺·Br⁻, the C—N bond lengths in the –S–C(NH₂)₂ fragment indicate partial double-bond character of these bonds. The constituent ions are connected by N—H⋯Br bridges into Z-shaped chains. The supramolecular architecture of the structure can be described by being composed of these chains interlocked by additional C—H⋯Br short contacts. An intramolecular N—H⋯O=C bridge, as well as weak C—H⋯O hydrogen bonds, are also present in the structure.

Related literature

For the preparation and reactivity of isothiuronium salts, see: Hanusek et al. (2004 ); Sedlák et al. (2002 , 2003 ). For related structures, see: Bel'skii et al. (1985 ); Cotton et al. (2006 ); Hanusek et al. (2009 ); Ishii et al. (2000 ); L'abbe et al. (1980 ); Luger et al. (1996 ); Rovnyak et al. (1995 ); Vijayan & Mani (1977 ).

Experimental

Crystal data

C₁₁H₁₃ClN₃OS⁺·Br⁻
M_r = 350.66
Monoclinic, P 2₁ /c
a = 15.7379 (9) Å
b = 6.4250 (5) Å
c = 15.0531 (7) Å
β = 117.329 (5)°
V = 1352.22 (16) Å³
Z = 4
Mo Kα radiation
μ = 3.38 mm⁻¹
T = 150 (2) K
0.29 × 0.12 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: gaussian (Coppens, 1970 ) T_min = 0.542, T_max = 0.873
15769 measured reflections
3095 independent reflections
2214 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.096
S = 1.15
3095 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AB⋯Br1	0.88	2.43	3.290 (3)	166
N2A—H2AA⋯Br1ⁱ	0.88	2.68	3.452 (3)	147
N2A—H2AA⋯Br1ⁱⁱ	0.88	2.91	3.426 (3)	119
N3A—H3AA⋯Br1ⁱ	0.88	2.44	3.273 (3)	158
N3A—H3AB⋯O1	0.88	2.12	2.823 (4)	137
C2—H2A⋯O1ⁱⁱⁱ	0.99	2.57	3.352 (5)	137
C3—H3B⋯Br1^iv	0.99	3.01	3.737 (4)	131
C10—H10⋯O1	0.95	2.22	2.852 (5)	124
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001603/fb2122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001603/fb2122Isup2.hkl

checkCIF report

Comment top

In our previous papers (Sedlák et al., 2002, 2003; Hanusek et al., 2004) we have reported that substituted S-(1-phenylpyrrolidin-2-on-3-yl)isothiuronium salts undergo an intramolecular recyclization reaction in a weak basic medium. During this reaction the γ-lactam cycle is split while a thiazolidine cycle, i.e. a substituted 2-imino-5-[2-(phenylamino)ethyl]thiazolidin-4-one, is formed.

A further interest has been provoked by a discovery (Sedlák et al., 2002, 2003; Hanusek et al., 2004) that N-unsubstituted isothiuronium salts undergo a transformation involving only a general base catalysis whereas in the case of N,N'-dimethylisothiuronium salts such a transformation is catalyzed by both acid and base buffer components.

In continuation of our above mentioned studies, the crystal structures of (3RS)-S-[1-(3-chlorophenyl)pyrrolidin-2-on-3-yl]isothiuronium bromide (Scheme 1, Figs. 1-3) and its N,N'-dimethyl derivative (Hanusek et al., 2009) were determined and the influence of the methyl substituents bound to the isothiuronium moiety was examined.

There is a limited number of X-ray structures of isothiouronium salts reported in the literature. Eleven of these are the compounds of the S–C(NH₂)₂ type with no replacement of the hydrogens that are pertinent to the –NH₂ group (e.g. Vijayan et al., 1977; Bel'skii et al., 1985; Ishii et al., 2000). The rest are the compounds where both nitrogen atoms are connected to a chain thus forming five- to eight-membered rings (e.g. Rovnyak et al., 1995; Cotton et al., 2006; Luger et al., 1996). There is only one example of a disubstituted acyclic species, N-methyl- N'-phenyl-S-sulfomethylisothiourea (L'abbe et al., 1980).

In the title structure and its N,N'-dimethyl derivative the respective interplanar angles between the S–C(NHR)₂ group and the heterocyclic rings are almost the same: 66.7 (1) ° and 71.3 (1) °. The S1–C11 distance (1.749 (4) Å) in the title structure fits to the literature range 1.717–1.760 Å - cf. 1.770 (4) Å in N,N'-dimethyl derivative. The C11–N2 and C11–N3 distances also agree to the literature range that is 1.258 - 1.326 Å. (In the title compound these distances are 1.312 (5), 1.296 (5) Å, respectively, while in the N,N'-dimethyl derivative these distances are 1.308 (5), 1.308 (5) Å, respectively).

These C-N bond lengths in the S–C(NH₂)₂ fragment of the title structure reveal a partly double bond character of these bonds. This is in accordance with planarity of this fragment. (The groups -NH₂ were therefore duly constrained during refinement.)

The interatomic angles C4–S1–C11 (104.56 (18)°) and N2–C11–N3 (122.0 (4)°) in the title compound are similar to those in the related N,N'-dimethyl derivative (98.75 (18)° and 122.6 (4)°, respectively) and also fall into the literature range which is 99.2–105.5° and 108.0—123.5°, respectively. The twist angles about the N1–C5 bonds, which show a mutual orientation of both rings, are 7.8 (1) and 29.7 (1) ° in the title compound and its N,N'-dimethyl derivative, respectively.

All the known isothiouronium cations reveal hydrogen bonding in the crystal structure. Also in the packing of the molecules of the title compound and its N,N'-dimethyl derivative such interactions are present. All the NH₂ hydrogen atoms are donated to the bromine atoms except for H3AB. Those with the shortest Br···H distances form infinite chains via the N2-H2AB···Br···H3AA-N3 motifs (Figs. 2 and 3; Tab. 1) with the angle H2AB···Br1···H3AA equal to 100.7 (1)°. There is also present an intramolecular N–H···O=C contact (Tab. 1, Fig. 2). The crystal packing can be described as H-bonded interlocked Z- shaped ribbons caused by the presence of additional short contacts C–H···Br (Fig. 3).

Related literature top

For the preparation and reactivity of isothiuronium salts, see: Hanusek et al. (2004); Sedlák et al. (2002, 2003). For related structures, see: Bel'skii et al. (1985); Cotton et al. (2006); Hanusek et al. (2009); Ishii et al. (2000); L'abbe et al. (1980); Luger et al. (1996); Rovnyak et al. (1995); Vijayan & Mani (1977).

Experimental top

The title compound was synthesized according to Hanusek et al. (2004) from saturated acetone solutions of the racemic 3-bromo-1-(3-chlorophenyl)pyrrolidin-2-one and thiourea. Suitable single crystals (plates) were grown directly from the reaction mixture. Their average size was 0.2×0.1×0.02 mm.

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule with the displacement ellipsoids shown on 50% probability level. The H atoms are shown with arbitrary radius.
	Fig. 2. View of the motif of the structure with the hydrogen bonding.
	Fig. 3. View of the unit cell along the axis c. The H bonding is depicted. Symmetry codes for Br1c: x, -1+y, z; for Br1d: 1-x, -1/2+y, 3/2-z; for another isothiuronium fragment: x, 1+y, z.

(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]thiouronium bromide top

Crystal data top

C₁₁H₁₃ClN₃OS⁺·Br⁻	F(000) = 704
M_r = 350.66	D_x = 1.722 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15779 reflections
a = 15.7379 (9) Å	θ = 1–27.5°
b = 6.4250 (5) Å	µ = 3.38 mm⁻¹
c = 15.0531 (7) Å	T = 150 K
β = 117.329 (5)°	Plate, colourless
V = 1352.22 (16) Å³	0.29 × 0.12 × 0.03 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	3095 independent reflections
Radiation source: fine-focus sealed tube	2214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ and ω scans	h = −20→20
Absorption correction: gaussian (Coppens, 1970)	k = −7→8
T_min = 0.542, T_max = 0.873	l = −19→19
15769 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0236P)² + 1.6718P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
3095 reflections	Δρ_max = 0.48 e Å⁻³
164 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
52 constraints	Extinction coefficient: 0.0036 (5)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₃ClN₃OS⁺·Br⁻	V = 1352.22 (16) Å³
M_r = 350.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.7379 (9) Å	µ = 3.38 mm⁻¹
b = 6.4250 (5) Å	T = 150 K
c = 15.0531 (7) Å	0.29 × 0.12 × 0.03 mm
β = 117.329 (5)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	3095 independent reflections
Absorption correction: gaussian (Coppens, 1970)	2214 reflections with I > 2σ(I)
T_min = 0.542, T_max = 0.873	R_int = 0.097
15769 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.15	Δρ_max = 0.48 e Å⁻³
3095 reflections	Δρ_min = −0.47 e Å⁻³
164 parameters

Special details top

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
Br1	0.48049 (3)	0.45589 (6)	0.65892 (3)	0.04086 (16)
S1	0.34553 (7)	0.14593 (15)	0.41198 (8)	0.0339 (2)
Cl1	−0.19436 (7)	0.30572 (19)	−0.02926 (9)	0.0532 (3)
O1	0.21265 (19)	−0.2562 (4)	0.2711 (2)	0.0450 (7)
C5	0.0464 (3)	0.0076 (6)	0.1482 (3)	0.0295 (8)
C6	−0.0184 (3)	0.1577 (6)	0.0890 (3)	0.0330 (9)
H6	0.0040	0.2871	0.0774	0.040*
C4	0.3119 (3)	0.0455 (6)	0.2870 (3)	0.0346 (9)
H4	0.3640	−0.0404	0.2852	0.042*
C11	0.3880 (2)	−0.0716 (6)	0.4901 (3)	0.0291 (8)
C2	0.1792 (3)	0.2598 (6)	0.1780 (3)	0.0372 (10)
H2A	0.1660	0.3657	0.2179	0.045*
H2B	0.1480	0.3027	0.1069	0.045*
C1	0.2191 (3)	−0.0747 (6)	0.2493 (3)	0.0329 (9)
C10	0.0120 (3)	−0.1790 (7)	0.1662 (3)	0.0398 (10)
H10	0.0552	−0.2828	0.2072	0.048*
C8	−0.1500 (3)	−0.0645 (7)	0.0639 (3)	0.0422 (10)
H8	−0.2169	−0.0891	0.0349	0.051*
C7	−0.1148 (3)	0.1186 (7)	0.0473 (3)	0.0375 (9)
C9	−0.0854 (3)	−0.2119 (7)	0.1239 (3)	0.0459 (11)
H9	−0.1085	−0.3394	0.1364	0.055*
C3	0.2862 (3)	0.2309 (7)	0.2163 (3)	0.0410 (10)
H3A	0.3216	0.3568	0.2522	0.049*
H3B	0.3012	0.2018	0.1605	0.049*
N2A	0.4287 (2)	−0.0308 (5)	0.5862 (2)	0.0359 (8)
H2AA	0.4517	−0.1329	0.6299	0.043*
H2AB	0.4331	0.0986	0.6070	0.043*
N1	0.1455 (2)	0.0527 (5)	0.1902 (2)	0.0301 (7)
N3A	0.3800 (2)	−0.2598 (5)	0.4563 (3)	0.0387 (8)
H3AA	0.4023	−0.3650	0.4982	0.046*
H3AB	0.3523	−0.2825	0.3914	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0583 (3)	0.0267 (2)	0.0360 (2)	−0.00529 (19)	0.0203 (2)	−0.00053 (19)
S1	0.0371 (5)	0.0258 (5)	0.0328 (5)	0.0008 (4)	0.0109 (4)	−0.0016 (4)
Cl1	0.0390 (6)	0.0562 (7)	0.0584 (7)	0.0075 (5)	0.0172 (5)	0.0116 (6)
O1	0.0468 (17)	0.0269 (16)	0.0439 (18)	−0.0033 (13)	0.0059 (13)	0.0010 (13)
C5	0.032 (2)	0.030 (2)	0.027 (2)	−0.0057 (15)	0.0133 (16)	−0.0075 (16)
C6	0.036 (2)	0.030 (2)	0.034 (2)	−0.0026 (17)	0.0161 (17)	0.0017 (17)
C4	0.034 (2)	0.037 (2)	0.032 (2)	−0.0007 (18)	0.0144 (17)	0.0001 (19)
C11	0.0234 (18)	0.025 (2)	0.039 (2)	−0.0001 (15)	0.0141 (16)	−0.0007 (17)
C2	0.037 (2)	0.030 (2)	0.040 (2)	−0.0071 (17)	0.0141 (18)	0.0067 (18)
C1	0.038 (2)	0.030 (2)	0.027 (2)	0.0000 (17)	0.0123 (17)	−0.0043 (17)
C10	0.040 (2)	0.036 (2)	0.038 (2)	−0.0058 (18)	0.0143 (19)	0.0043 (19)
C8	0.035 (2)	0.056 (3)	0.034 (2)	−0.014 (2)	0.0140 (18)	−0.002 (2)
C7	0.038 (2)	0.043 (2)	0.033 (2)	0.0007 (19)	0.0176 (18)	−0.0003 (19)
C9	0.048 (2)	0.041 (3)	0.047 (3)	−0.015 (2)	0.020 (2)	0.004 (2)
C3	0.038 (2)	0.048 (3)	0.038 (2)	−0.0066 (19)	0.0177 (19)	0.007 (2)
N2A	0.0434 (19)	0.0261 (16)	0.0307 (19)	−0.0003 (15)	0.0104 (15)	−0.0017 (15)
N1	0.0291 (16)	0.0265 (16)	0.0319 (18)	−0.0045 (14)	0.0116 (14)	−0.0010 (14)
N3A	0.049 (2)	0.0262 (18)	0.0327 (19)	0.0049 (15)	0.0117 (16)	−0.0026 (15)

Geometric parameters (Å, º) top

S1—C11	1.749 (4)	C2—H2A	0.9900
S1—C4	1.822 (4)	C2—H2B	0.9900
Cl1—C7	1.737 (4)	C1—N1	1.363 (5)
O1—C1	1.228 (4)	C10—C9	1.379 (6)
C5—C6	1.389 (5)	C10—H10	0.9500
C5—C10	1.392 (5)	C8—C7	1.371 (6)
C5—N1	1.418 (4)	C8—C9	1.380 (6)
C6—C7	1.374 (5)	C8—H8	0.9500
C6—H6	0.9500	C9—H9	0.9500
C4—C1	1.514 (5)	C3—H3A	0.9900
C4—C3	1.523 (5)	C3—H3B	0.9900
C4—H4	1.0000	N2A—H2AA	0.8800
C11—N3A	1.296 (5)	N2A—H2AB	0.8800
C11—N2A	1.312 (5)	N3A—H3AA	0.8800
C2—N1	1.475 (5)	N3A—H3AB	0.8800
C2—C3	1.520 (5)

C11—S1—C4	104.56 (18)	C9—C10—H10	120.3
C6—C5—C10	119.1 (3)	C5—C10—H10	120.3
C6—C5—N1	118.5 (3)	C7—C8—C9	118.0 (4)
C10—C5—N1	122.4 (3)	C7—C8—H8	121.0
C7—C6—C5	119.9 (4)	C9—C8—H8	121.0
C7—C6—H6	120.1	C8—C7—C6	121.9 (4)
C5—C6—H6	120.1	C8—C7—Cl1	119.1 (3)
C1—C4—C3	103.7 (3)	C6—C7—Cl1	119.0 (3)
C1—C4—S1	109.9 (3)	C10—C9—C8	121.8 (4)
C3—C4—S1	107.6 (3)	C10—C9—H9	119.1
C1—C4—H4	111.8	C8—C9—H9	119.1
C3—C4—H4	111.8	C2—C3—C4	104.7 (3)
S1—C4—H4	111.8	C2—C3—H3A	110.8
N3A—C11—N2A	122.0 (4)	C4—C3—H3A	110.8
N3A—C11—S1	122.9 (3)	C2—C3—H3B	110.8
N2A—C11—S1	115.1 (3)	C4—C3—H3B	110.8
N1—C2—C3	104.0 (3)	H3A—C3—H3B	108.9
N1—C2—H2A	111.0	C11—N2A—H2AA	120.0
C3—C2—H2A	111.0	C11—N2A—H2AB	120.0
N1—C2—H2B	111.0	H2AA—N2A—H2AB	120.0
C3—C2—H2B	111.0	C1—N1—C5	126.8 (3)
H2A—C2—H2B	109.0	C1—N1—C2	112.1 (3)
O1—C1—N1	126.5 (4)	C5—N1—C2	120.9 (3)
O1—C1—C4	124.6 (4)	C11—N3A—H3AA	120.0
N1—C1—C4	108.8 (3)	C11—N3A—H3AB	120.0
C9—C10—C5	119.4 (4)	H3AA—N3A—H3AB	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AB···Br1	0.88	2.43	3.290 (3)	166
N2A—H2AA···Br1ⁱ	0.88	2.68	3.452 (3)	147
N2A—H2AA···Br1ⁱⁱ	0.88	2.91	3.426 (3)	119
N3A—H3AA···Br1ⁱ	0.88	2.44	3.273 (3)	158
N3A—H3AB···O1	0.88	2.12	2.823 (4)	137
C2—H2A···O1ⁱⁱⁱ	0.99	2.57	3.352 (5)	137
C3—H3B···Br1^iv	0.99	3.01	3.737 (4)	131
C10—H10···O1	0.95	2.22	2.852 (5)	124

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃ClN₃OS⁺·Br⁻
M_r	350.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.7379 (9), 6.4250 (5), 15.0531 (7)
β (°)	117.329 (5)
V (Å³)	1352.22 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.38
Crystal size (mm)	0.29 × 0.12 × 0.03

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.542, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	15769, 3095, 2214
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.096, 1.15
No. of reflections	3095
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.47

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AB···Br1	0.88	2.43	3.290 (3)	165.9
N2A—H2AA···Br1ⁱ	0.88	2.68	3.452 (3)	146.8
N2A—H2AA···Br1ⁱⁱ	0.88	2.91	3.426 (3)	119.3
N3A—H3AA···Br1ⁱ	0.88	2.44	3.273 (3)	157.9
N3A—H3AB···O1	0.88	2.12	2.823 (4)	136.6
C2—H2A···O1ⁱⁱⁱ	0.99	2.57	3.352 (5)	137
C3—H3B···Br1^iv	0.99	3.01	3.737 (4)	131
C10—H10···O1	0.95	2.22	2.852 (5)	123.5

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Ministry of Education, Youth and Sports of the Czech Republic for financial support of this work within the framework of research project MSM 0021627501.

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