Sodium N-bromo-2,4-dichloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Fuess, H.

doi:10.1107/S1600536807033144

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Sodium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate

B. T. Gowda, M. Tokarčík, J. Kožíšek and H. Fuess

The title compound [systematic name: μ₂-aqua-diaquabis(μ₃-N-bromo-2,4-dichlorobenzenesulfonamidato)disodium(I)], Na⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O, crystallizes with two sodium cations, two N-bromo-2,4-dichlorobenzenesulfonamidate anions and three water molecules in the asymmetric unit, similar to sodium N-bromobenzenesulfonamidate, sodium N-bromo-4-chlorobenzenesulfonamidate and sodium N-bromo-2-methyl-4-chlorobenzenesulfonamidate. A crystallographic twofold rotation axis passes through one of the water molecules. There is no interaction between the nitrogen atoms and sodium ions. The sodium ion shows octahedral coordination by three O atoms of water molecules and by three sulfonyl O atoms of three different N-bromo-2,4-dichlorobenzenesulfonamidate anions. The S—N distance of 1.590 (6) Å is consistent with an S=N double bond. The Na⁺ ion coordination in the structure gives rise to several hydrogen bonds between water molecules and N or Br atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033144/dn2212sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033144/dn2212Isup2.hkl Contains datablock I

CCDC reference: 614775

checkCIF report

Key indicators

Single-crystal X-ray study
T = 304 K
Mean (C-C) = 0.011 Å
R factor = 0.062
wR factor = 0.177
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.37 Ratio

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of N-bromo-arylsulfonamides is of interest due to their diverse characteristics (Usha & Gowda, 2006). In the present work, the structure of sodium N-bromo-2,4-dichloro-benzenesulfonamidate (NaNB24DCBSA) has been determined to explore the substituent effects on the solid state structures of arylsulfonamides and N-halo arylsulfonamidates (Gowda et al., 2007a,b; Gowda, Savitha et al. 2007; Gowda, Usha et al., 2007). The structure of NaNB24DCBSA (Fig. 1) is similar to those of sodium N-chloro-2,4-dichloro-benzenesulfonamidate (NaNC24DCBSA) (Gowda, Savitha et al., 2007), sodium N-bromo-benzenesulfonamidate (NaNBBSA) (Gowda et al., 2007d), sodium N-bromo-4-chloro- benzenesulfonamidate (NaNB4CBSA) (Gowda et al., 2007a) and sodium N-bromo-2-methyl-4-chloro-benzenesulfonamidate (Gowda et al., 2007b). NaNB24DCBSA crystallizes with two sodium cations, two N-bromo-2,4-dichloro-benzenesulfonamidate anions and three water molecules in the asymmetric unit. One of the water molecules is located on a special position. Further, the sodium ion shows octahedral coordination by three O atoms of three different water molecules and by three sulfonyl O atoms of three different N-bromo-2,4-dichloro-benzenesulfonamidate anions. There is no interaction between the nitrogen and sodium ions in the molecule. The S—N distances of N1—S1, 1.590 (6)Å is consistent with a S—N double bond and in agreement with those observed with NaNBBSA, NaNB4CBSA, NaNB2M4CBSA and NaNC24DCBSA. The Na+ ion coordination in the structure gives rise to several hydrogen bonding between water hydrogen, oxygen and nitrogen or bromine atoms in the molecule (Table 1).

Related literature top

For related literature, see: Gowda et al. (2007a,b); Gowda, Savitha et al. (2007); Gowda & Usha (2003); Gowda, Usha et al. (2007); Usha & Gowda (2006).

Experimental top

The title compound was prepared according to the literature method (Gowda & Usha, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda & Usha, 2003). Single crystals of the title compound were obtained from its aqueous solution and used for X-ray diffraction studies at room temperature.

Structure description top

For related literature, see: Gowda et al. (2007a,b); Gowda, Savitha et al. (2007); Gowda & Usha (2003); Gowda, Usha et al. (2007); Usha & Gowda (2006).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Diamond (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. ORTEP view of the title compound showing the atom labelling scheme. H atoms are represented as small spheres of arbitrary radii. Water molecule Ow3 is located on a two fold axis (1/2, 1/2 + y, 1/4). Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1 - x, y, 1/2 - z].

Sodium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate top

Crystal data top

Na⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O	F(000) = 1384
M_r = 707.96	D_x = 2.067 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2198 reflections
a = 11.1170 (15) Å	θ = 2.5–26.4°
b = 6.780 (1) Å	µ = 4.29 mm⁻¹
c = 30.567 (4) Å	T = 304 K
β = 99.124 (15)°	Plate, yellow
V = 2274.8 (6) Å³	0.60 × 0.33 × 0.11 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2094 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Rotation method data acquisition using ω and phi scans	θ_max = 26.0°, θ_min = 5.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003; Clark & Reid, 1995)	h = −13→13
T_min = 0.195, T_max = 0.627	k = −8→8
3121 measured reflections	l = −36→37
2200 independent 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0925P)² + 47.8P] where P = (F_o² + 2F_c²)/3
2200 reflections	(Δ/σ)_max = 0.002
148 parameters	Δρ_max = 1.06 e Å⁻³
5 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

Na⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O	V = 2274.8 (6) Å³
M_r = 707.96	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.1170 (15) Å	µ = 4.29 mm⁻¹
b = 6.780 (1) Å	T = 304 K
c = 30.567 (4) Å	0.60 × 0.33 × 0.11 mm
β = 99.124 (15)°

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2200 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003; Clark & Reid, 1995)	2094 reflections with I > 2σ(I)
T_min = 0.195, T_max = 0.627	R_int = 0.065
3121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	5 restraints
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0925P)² + 47.8P] where P = (F_o² + 2F_c²)/3
2200 reflections	Δρ_max = 1.06 e Å⁻³
148 parameters	Δρ_min = −1.00 e Å⁻³

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
C1	0.3275 (6)	0.1809 (9)	0.1192 (2)	0.0183 (12)
C2	0.4084 (7)	0.1212 (10)	0.0912 (2)	0.0219 (13)
C3	0.3665 (8)	0.0504 (11)	0.0492 (2)	0.0319 (17)
H3	0.4213	0.0098	0.031	0.038*
C4	0.2426 (8)	0.0402 (11)	0.0345 (3)	0.0354 (18)
C5	0.1588 (7)	0.0946 (12)	0.0613 (3)	0.0354 (18)
H5	0.0755	0.0843	0.0514	0.042*
C6	0.2028 (6)	0.1643 (11)	0.1032 (3)	0.0279 (16)
H6	0.1475	0.2018	0.1215	0.033*
N1	0.4651 (5)	0.4579 (8)	0.17108 (18)	0.0203 (11)
O1	0.4400 (5)	0.1331 (7)	0.20070 (16)	0.0254 (10)
O2	0.2573 (5)	0.3374 (8)	0.18720 (17)	0.0292 (12)
O3W	0.5	−0.2706 (11)	0.25	0.0289 (15)
H31	0.529 (8)	−0.332 (12)	0.275 (2)	0.035*
O4W	0.7099 (5)	0.3237 (9)	0.20865 (19)	0.0318 (12)
H41	0.745 (8)	0.302 (11)	0.187 (2)	0.038*
H42	0.647 (5)	0.369 (10)	0.196 (3)	0.038*
S1	0.37118 (14)	0.2828 (2)	0.17335 (5)	0.0174 (4)
Na1	0.6445 (3)	−0.0014 (4)	0.23596 (10)	0.0287 (6)
Cl1	0.56406 (16)	0.1333 (3)	0.10764 (7)	0.0358 (5)
Cl2	0.1903 (3)	−0.0354 (3)	−0.01953 (7)	0.0553 (7)
Br1	0.39296 (7)	0.65862 (11)	0.13323 (2)	0.0301 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.019 (3)	0.018 (3)	0.018 (3)	−0.003 (2)	0.001 (2)	0.000 (2)
C2	0.033 (4)	0.019 (3)	0.014 (3)	0.003 (3)	0.006 (3)	0.000 (2)
C3	0.055 (5)	0.018 (3)	0.024 (4)	0.006 (3)	0.010 (3)	−0.008 (3)
C4	0.051 (5)	0.016 (3)	0.033 (4)	−0.004 (3)	−0.010 (4)	−0.003 (3)
C5	0.029 (4)	0.033 (4)	0.038 (4)	−0.005 (3)	−0.012 (3)	−0.003 (3)
C6	0.020 (3)	0.031 (4)	0.032 (4)	−0.004 (3)	−0.001 (3)	0.001 (3)
N1	0.019 (3)	0.019 (3)	0.022 (3)	0.000 (2)	0.003 (2)	0.003 (2)
O1	0.029 (2)	0.024 (2)	0.023 (2)	0.002 (2)	0.001 (2)	0.0059 (19)
O2	0.023 (2)	0.041 (3)	0.027 (3)	0.007 (2)	0.014 (2)	−0.005 (2)
O3W	0.041 (4)	0.025 (4)	0.018 (3)	0	−0.003 (3)	0
O4W	0.022 (3)	0.038 (3)	0.036 (3)	0.002 (2)	0.005 (2)	0.000 (2)
S1	0.0200 (7)	0.0177 (7)	0.0153 (7)	0.0002 (6)	0.0051 (6)	0.0010 (6)
Na1	0.0290 (14)	0.0299 (15)	0.0292 (15)	0.0037 (12)	0.0107 (12)	−0.0006 (12)
Cl1	0.0228 (8)	0.0442 (11)	0.0429 (11)	0.0029 (7)	0.0124 (7)	−0.0097 (9)
Cl2	0.0911 (19)	0.0350 (11)	0.0295 (10)	0.0023 (12)	−0.0216 (11)	−0.0077 (8)
Br1	0.0347 (5)	0.0246 (4)	0.0323 (4)	0.0024 (3)	0.0090 (3)	0.0059 (3)

Geometric parameters (Å, º) top

C1—C2	1.397 (9)	O1—Na1	2.526 (6)
C1—C6	1.399 (9)	O2—S1	1.445 (5)
C1—S1	1.788 (7)	O2—Na1ⁱⁱ	2.363 (5)
C2—C3	1.380 (10)	O3W—Na1	2.513 (6)
C2—Cl1	1.726 (7)	O3W—Na1ⁱ	2.513 (6)
C3—C4	1.381 (12)	O3W—H31	0.88 (5)
C3—H3	0.93	O4W—Na1ⁱⁱⁱ	2.454 (6)
C4—C5	1.386 (13)	O4W—Na1	2.505 (7)
C4—Cl2	1.739 (8)	O4W—H41	0.82 (5)
C5—C6	1.378 (11)	O4W—H42	0.80 (5)
C5—H5	0.93	Na1—O2^iv	2.363 (5)
C6—H6	0.93	Na1—O4W^v	2.454 (6)
N1—S1	1.590 (6)	Na1—O1ⁱ	2.458 (6)
N1—Br1	1.881 (5)	Na1—Na1ⁱ	3.455 (5)
O1—S1	1.453 (5)	Na1—Na1ⁱⁱⁱ	4.134 (3)
O1—Na1ⁱ	2.458 (6)	Na1—Na1^v	4.134 (3)

C2—C1—C6	117.4 (6)	N1—S1—C1	109.4 (3)
C2—C1—S1	124.9 (5)	O2^iv—Na1—O4W^v	81.6 (2)
C6—C1—S1	117.7 (5)	O2^iv—Na1—O1ⁱ	167.5 (2)
C3—C2—C1	121.1 (7)	O4W^v—Na1—O1ⁱ	85.9 (2)
C3—C2—Cl1	117.6 (6)	O2^iv—Na1—O4W	89.2 (2)
C1—C2—Cl1	121.4 (5)	O4W^v—Na1—O4W	117.42 (17)
C2—C3—C4	119.5 (7)	O1ⁱ—Na1—O4W	95.9 (2)
C2—C3—H3	120.2	O2^iv—Na1—O3W	100.9 (2)
C4—C3—H3	120.2	O4W^v—Na1—O3W	84.32 (17)
C3—C4—C5	121.5 (7)	O1ⁱ—Na1—O3W	78.48 (17)
C3—C4—Cl2	119.4 (7)	O4W—Na1—O3W	157.4 (2)
C5—C4—Cl2	119.1 (6)	O2^iv—Na1—O1	115.4 (2)
C6—C5—C4	117.9 (7)	O4W^v—Na1—O1	156.8 (2)
C6—C5—H5	121.1	O1ⁱ—Na1—O1	76.8 (2)
C4—C5—H5	121.1	O4W—Na1—O1	80.15 (19)
C5—C6—C1	122.6 (7)	O3W—Na1—O1	77.22 (17)
C5—C6—H6	118.7	O2^iv—Na1—Na1ⁱ	139.86 (18)
C1—C6—H6	118.7	O4W^v—Na1—Na1ⁱ	111.49 (17)
S1—N1—Br1	110.4 (3)	O1ⁱ—Na1—Na1ⁱ	46.95 (13)
S1—O1—Na1ⁱ	118.7 (3)	O4W—Na1—Na1ⁱ	114.39 (14)
S1—O1—Na1	148.6 (3)	O3W—Na1—Na1ⁱ	46.58 (13)
Na1ⁱ—O1—Na1	87.74 (18)	O1—Na1—Na1ⁱ	45.31 (13)
S1—O2—Na1ⁱⁱ	151.7 (3)	O2^iv—Na1—Na1ⁱⁱⁱ	99.78 (18)
Na1—O3W—Na1ⁱ	86.8 (3)	O4W^v—Na1—Na1ⁱⁱⁱ	87.84 (18)
Na1—O3W—H31	109 (6)	O1ⁱ—Na1—Na1ⁱⁱⁱ	78.90 (14)
Na1ⁱ—O3W—H31	111 (6)	O4W—Na1—Na1ⁱⁱⁱ	33.14 (13)
Na1ⁱⁱⁱ—O4W—Na1	112.9 (2)	O3W—Na1—Na1ⁱⁱⁱ	156.51 (15)
Na1ⁱⁱⁱ—O4W—H41	106 (6)	O1—Na1—Na1ⁱⁱⁱ	103.59 (13)
Na1—O4W—H41	108 (5)	Na1ⁱ—Na1—Na1ⁱⁱⁱ	117.89 (8)
Na1ⁱⁱⁱ—O4W—H42	125 (6)	O2^iv—Na1—Na1^v	53.92 (15)
Na1—O4W—H42	103 (5)	O4W^v—Na1—Na1^v	33.93 (15)
H41—O4W—H42	100 (10)	O1ⁱ—Na1—Na1^v	114.58 (17)
O2—S1—O1	114.6 (3)	O4W—Na1—Na1^v	127.28 (18)
O2—S1—N1	115.7 (3)	O3W—Na1—Na1^v	74.09 (12)
O1—S1—N1	104.9 (3)	O1—Na1—Na1^v	145.79 (16)
O2—S1—C1	104.4 (3)	Na1ⁱ—Na1—Na1^v	117.89 (8)
O1—S1—C1	107.7 (3)	Na1ⁱⁱⁱ—Na1—Na1^v	110.17 (13)

C6—C1—C2—C3	0.5 (10)	C6—C1—S1—N1	−127.7 (5)
S1—C1—C2—C3	−177.7 (5)	Na1ⁱⁱⁱ—O4W—Na1—O2^iv	−109.4 (3)
C6—C1—C2—Cl1	−179.5 (5)	Na1ⁱⁱⁱ—O4W—Na1—O4W^v	−29.3 (3)
S1—C1—C2—Cl1	2.3 (9)	Na1ⁱⁱⁱ—O4W—Na1—O1ⁱ	59.1 (2)
C1—C2—C3—C4	0.7 (11)	Na1ⁱⁱⁱ—O4W—Na1—O3W	133.3 (4)
Cl1—C2—C3—C4	−179.3 (6)	Na1ⁱⁱⁱ—O4W—Na1—O1	134.6 (3)
C2—C3—C4—C5	−1.8 (12)	Na1ⁱⁱⁱ—O4W—Na1—Na1ⁱ	104.2 (2)
C2—C3—C4—Cl2	176.3 (5)	Na1ⁱⁱⁱ—O4W—Na1—Na1^v	−68.1 (3)
C3—C4—C5—C6	1.6 (12)	Na1ⁱ—O3W—Na1—O2^iv	−152.8 (2)
Cl2—C4—C5—C6	−176.5 (6)	Na1ⁱ—O3W—Na1—O4W^v	126.95 (18)
C4—C5—C6—C1	−0.3 (12)	Na1ⁱ—O3W—Na1—O1ⁱ	39.98 (13)
C2—C1—C6—C5	−0.7 (11)	Na1ⁱ—O3W—Na1—O4W	−37.6 (5)
S1—C1—C6—C5	177.6 (6)	Na1ⁱ—O3W—Na1—O1	−38.90 (13)
Na1ⁱⁱ—O2—S1—O1	73.5 (8)	Na1ⁱ—O3W—Na1—Na1ⁱⁱⁱ	55.8 (3)
Na1ⁱⁱ—O2—S1—N1	−48.8 (8)	Na1ⁱ—O3W—Na1—Na1^v	159.94 (14)
Na1ⁱⁱ—O2—S1—C1	−169.0 (7)	S1—O1—Na1—O2^iv	−74.9 (6)
Na1ⁱ—O1—S1—O2	0.2 (4)	Na1ⁱ—O1—Na1—O2^iv	136.06 (18)
Na1—O1—S1—O2	−143.9 (6)	S1—O1—Na1—O4W^v	150.9 (6)
Na1ⁱ—O1—S1—N1	128.2 (3)	Na1ⁱ—O1—Na1—O4W^v	1.8 (6)
Na1—O1—S1—N1	−16.0 (7)	S1—O1—Na1—O1ⁱ	108.0 (5)
Na1ⁱ—O1—S1—C1	−115.4 (3)	Na1ⁱ—O1—Na1—O1ⁱ	−41.1 (2)
Na1—O1—S1—C1	100.5 (6)	S1—O1—Na1—O4W	9.5 (6)
Br1—N1—S1—O2	−56.7 (4)	Na1ⁱ—O1—Na1—O4W	−139.6 (2)
Br1—N1—S1—O1	176.0 (3)	S1—O1—Na1—O3W	−171.0 (6)
Br1—N1—S1—C1	60.8 (4)	Na1ⁱ—O1—Na1—O3W	39.91 (15)
C2—C1—S1—O2	174.8 (6)	S1—O1—Na1—Na1ⁱ	149.1 (7)
C6—C1—S1—O2	−3.4 (6)	S1—O1—Na1—Na1ⁱⁱⁱ	33.1 (6)
C2—C1—S1—O1	−63.0 (6)	Na1ⁱ—O1—Na1—Na1ⁱⁱⁱ	−115.97 (17)
C6—C1—S1—O1	118.8 (6)	S1—O1—Na1—Na1^v	−137.5 (5)
C2—C1—S1—N1	50.5 (7)	Na1ⁱ—O1—Na1—Na1^v	73.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H42···N1	0.80 (5)	2.13 (5)	2.925 (8)	169 (8)
O3W—H31···N1^vi	0.88 (5)	2.18 (6)	3.010 (7)	158 (8)
O3W—H31···Br1^vi	0.88 (5)	2.81 (6)	3.6109 (13)	152 (8)
O4W—H41···Br1^iv	0.82 (5)	2.69 (5)	3.493 (6)	165 (8)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O
M_r	707.96
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	304
a, b, c (Å)	11.1170 (15), 6.780 (1), 30.567 (4)
β (°)	99.124 (15)
V (Å³)	2274.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.29
Crystal size (mm)	0.60 × 0.33 × 0.11

Data collection
Diffractometer	Oxford Diffraction Xcalibur CCD
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2003; Clark & Reid, 1995)
T_min, T_max	0.195, 0.627
No. of measured, independent and observed [I > 2σ(I)] reflections	3121, 2200, 2094
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.177, 1.09
No. of reflections	2200
No. of parameters	148
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0925P)² + 47.8P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.06, −1.00

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), CrysAlis RED, SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Diamond (Brandenburg, 2002), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H42···N1	0.80 (5)	2.13 (5)	2.925 (8)	169 (8)
O3W—H31···N1ⁱ	0.88 (5)	2.18 (6)	3.010 (7)	158 (8)
O3W—H31···Br1ⁱ	0.88 (5)	2.81 (6)	3.6109 (13)	152 (8)
O4W—H41···Br1ⁱⁱ	0.82 (5)	2.69 (5)	3.493 (6)	165 (8)

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

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