2-Amino-4-tert-butyl-5-(2-chloro­benz­yl)thia­zol-3-ium bromide

Cao, G.; Hu, A.-X.; Xu, J.-J.; Xia, L.

doi:10.1107/S1600536807018065

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2-Amino-4-tert-butyl-5-(2-chlorobenzyl)thiazol-3-ium bromide

G. Cao, A.-X. Hu, J.-J. Xu and L. Xia

As part of a search for potent fungicidal agents, the title compound, C₁₄H₁₈ClN₂S⁺·Br⁻, has been synthesized. The dihedral angle between the planes of the thiazole and the chlorophenyl ring is 95.1 (2)°. The molecules are connecteded by N—H

Br hydrogen bonds. The tert-butyl group shows rotational disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018065/bt2341sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018065/bt2341Isup2.hkl Contains datablock I

CCDC reference: 647603

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.053
wR factor = 0.158
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.53
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H6AC    ..       1.93 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

2-Amino-4-arylthiazoles have been utilized extensively by chemists due to their pharmaceutical importance in drug design and extensive application in organic synthesis (Marcantonio et al., 2002). The biological utility of 2-amino-4-arylthiazoles is wide-ranging, especially because of their antifungal activities. Two 2-Amino-4-arylthiazoles crystal structures were reported before (He et al., 2006; Xu et al., 2007). The title compound (I) was prepared as part of an ongoing investigation on the synthesis and structural properties of 2-amino-4-arylthiazole derivatives.

The dihedral angle between the chlorophenyl and thiazole ring planes is 95.1 (2)°. The molecules are linked by N–H···Br hydrogen bonds.

Related literature top

For related literature, see: He et al. (2006); Marcantonio et al. (2002); Xu et al. (2007).

Experimental top

1-(2-Chlorophenyl)-4,4-dimethylpentan-3-one (0.0067 mol) was dissolved in 267 ml e thanol and the mixture was stirred and heated to reflux. Cupric bromide (0.133 mol) was added to the reaction mixture in batches and the course of the reaction was followed by TLC analysis. After the reaction had finished, the mixture was filtered and concentrated in vacuo. The resulting residue was taken up in dichloromethane, washed with 10% hydrochloric acid, then washed with water until the solution was neutral, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2-bromo-1-(2-chlorophenyl)-4,4-dimethylpentan-3-one, yield 90.8%. Then a solution of thiourea (0.03 mol) and the bromide (0.03 mol) in ethanol (82 ml) was refluxed for 9 h. The solvent was evaporated and the precipitate formed was filtered out, dried, giving white crystals of (I), yield 63.2%. The crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

Structure description top

The dihedral angle between the chlorophenyl and thiazole ring planes is 95.1 (2)°. The molecules are linked by N–H···Br hydrogen bonds.

For related literature, see: He et al. (2006); Marcantonio et al. (2002); Xu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids, H atoms are drawn as spheres of arbitrary radii. Only the major occupied sites of the disordered tert-butyl group are shown.
	Fig. 2. The packing of (I), viewed down the a axis, showing the N—H···Br hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted. Only the major occupied sites of the disordered tert-butyl group are shown.

2-Amino-4-tert-butyl-5-(2-chlorobenzyl)thiazol-3-ium bromide top

Crystal data top

C₁₄H₁₈ClN₂S⁺·Br⁻	F(000) = 736
M_r = 361.72	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4663 reflections
a = 9.4439 (5) Å	θ = 2.2–26.9°
b = 14.5569 (8) Å	µ = 2.80 mm⁻¹
c = 12.1926 (6) Å	T = 173 K
β = 102.988 (1)°	Block, colorless
V = 1633.28 (15) Å³	0.48 × 0.39 × 0.32 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.302, T_max = 0.407	k = −17→17
10068 measured reflections	l = −14→15

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0807P)² + 4.4972P] where P = (F_o² + 2F_c²)/3
3203 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 2.10 e Å⁻³
117 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

C₁₄H₁₈ClN₂S⁺·Br⁻	V = 1633.28 (15) Å³
M_r = 361.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4439 (5) Å	µ = 2.80 mm⁻¹
b = 14.5569 (8) Å	T = 173 K
c = 12.1926 (6) Å	0.48 × 0.39 × 0.32 mm
β = 102.988 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3203 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2545 reflections with I > 2σ(I)
T_min = 0.302, T_max = 0.407	R_int = 0.023
10068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	117 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.05	Δρ_max = 2.10 e Å⁻³
3203 reflections	Δρ_min = −0.83 e Å⁻³
200 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	Occ. (<1)
Br1	0.70549 (6)	0.19049 (4)	0.14190 (4)	0.0487 (2)
S1	0.41454 (15)	0.14640 (11)	0.47178 (11)	0.0561 (4)
Cl1	−0.00232 (19)	0.19312 (14)	0.40805 (16)	0.0836 (6)
C1	0.5088 (5)	0.1765 (3)	0.3711 (4)	0.0423 (11)
C2	0.3359 (5)	0.0752 (3)	0.2738 (4)	0.0406 (10)
C3	0.2996 (5)	0.0735 (4)	0.3747 (4)	0.0475 (12)
C4	0.2775 (6)	0.0254 (4)	0.1637 (4)	0.0462 (11)
C5	0.2212 (12)	0.0923 (6)	0.0703 (7)	0.091 (3)	0.852 (10)
H5A	0.1405	0.1275	0.0878	0.136*	0.852 (10)
H5B	0.1871	0.0588	−0.0004	0.136*	0.852 (10)
H5C	0.2993	0.1345	0.0625	0.136*	0.852 (10)
C6	0.4073 (9)	−0.0285 (6)	0.1333 (8)	0.075 (2)	0.852 (10)
H6A	0.4581	−0.0637	0.1990	0.112*	0.852 (10)
H6B	0.4749	0.0150	0.1111	0.112*	0.852 (10)
H6C	0.3699	−0.0707	0.0708	0.112*	0.852 (10)
C7	0.1650 (9)	−0.0479 (6)	0.1718 (7)	0.067 (2)	0.852 (10)
H7A	0.0774	−0.0185	0.1859	0.101*	0.852 (10)
H7B	0.2051	−0.0900	0.2337	0.101*	0.852 (10)
H7C	0.1401	−0.0824	0.1010	0.101*	0.852 (10)
C5A	0.112 (4)	0.066 (3)	0.122 (4)	0.069 (8)	0.148 (10)
H5AA	0.0729	0.0799	0.1884	0.104*	0.148 (10)
H5AB	0.0506	0.0200	0.0758	0.104*	0.148 (10)
H5AC	0.1142	0.1220	0.0785	0.104*	0.148 (10)
C6A	0.357 (4)	0.026 (3)	0.086 (3)	0.060 (8)	0.148 (10)
H6AA	0.3259	0.0769	0.0342	0.090*	0.148 (10)
H6AB	0.3425	−0.0323	0.0446	0.090*	0.148 (10)
H6AC	0.4594	0.0329	0.1231	0.090*	0.148 (10)
C7A	0.245 (5)	−0.076 (3)	0.205 (4)	0.064 (8)	0.148 (10)
H7AA	0.1514	−0.0756	0.2271	0.096*	0.148 (10)
H7AB	0.3222	−0.0931	0.2702	0.096*	0.148 (10)
H7AC	0.2422	−0.1197	0.1441	0.096*	0.148 (10)
C8	0.1870 (7)	0.0204 (4)	0.4199 (5)	0.0593 (15)
H8A	0.0939	0.0208	0.3631	0.071*
H8B	0.2190	−0.0442	0.4329	0.071*
C9	0.1633 (5)	0.0608 (3)	0.5289 (4)	0.0444 (11)
C10	0.0812 (5)	0.1407 (4)	0.5319 (5)	0.0507 (13)
C11	0.0658 (6)	0.1785 (4)	0.6355 (5)	0.0529 (14)
H11	0.0107	0.2328	0.6376	0.064*
C12	0.1315 (6)	0.1350 (4)	0.7312 (5)	0.0559 (14)
H12	0.1241	0.1603	0.8015	0.067*
C13	0.2078 (7)	0.0564 (4)	0.7296 (5)	0.0600 (15)
H13	0.2507	0.0263	0.7982	0.072*
C14	0.2227 (6)	0.0206 (4)	0.6304 (5)	0.0537 (13)
H14	0.2766	−0.0346	0.6311	0.064*
N1	0.4537 (4)	0.1344 (3)	0.2742 (3)	0.0370 (8)
H1	0.4889	0.1430	0.2140	0.044*
N2	0.6226 (5)	0.2309 (3)	0.3875 (4)	0.0559 (12)
H2A	0.6671	0.2412	0.3325	0.067*
H2B	0.6545	0.2571	0.4535	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0529 (3)	0.0666 (4)	0.0289 (3)	−0.0152 (2)	0.0142 (2)	0.0046 (2)
S1	0.0563 (8)	0.0763 (10)	0.0442 (7)	−0.0278 (7)	0.0294 (6)	−0.0254 (7)
Cl1	0.0602 (9)	0.1074 (14)	0.0811 (12)	0.0073 (9)	0.0117 (8)	0.0524 (10)
C1	0.043 (3)	0.047 (3)	0.042 (3)	−0.010 (2)	0.019 (2)	−0.015 (2)
C2	0.035 (2)	0.049 (3)	0.041 (2)	−0.011 (2)	0.0145 (19)	−0.010 (2)
C3	0.047 (3)	0.056 (3)	0.043 (3)	−0.015 (2)	0.018 (2)	−0.015 (2)
C4	0.048 (3)	0.055 (3)	0.034 (2)	−0.010 (2)	0.0058 (19)	−0.008 (2)
C5	0.123 (7)	0.078 (5)	0.055 (4)	−0.003 (4)	−0.017 (4)	0.003 (4)
C6	0.065 (4)	0.083 (5)	0.078 (5)	−0.013 (3)	0.019 (4)	−0.044 (4)
C7	0.067 (4)	0.083 (5)	0.054 (4)	−0.034 (4)	0.019 (3)	−0.022 (3)
C5A	0.062 (9)	0.074 (11)	0.068 (12)	0.009 (9)	0.006 (8)	−0.009 (9)
C6A	0.063 (10)	0.067 (12)	0.052 (11)	−0.005 (8)	0.019 (8)	−0.007 (8)
C7A	0.070 (12)	0.061 (9)	0.062 (12)	−0.005 (8)	0.015 (9)	−0.003 (8)
C8	0.060 (3)	0.070 (4)	0.056 (3)	−0.024 (3)	0.031 (3)	−0.012 (3)
C9	0.038 (2)	0.050 (3)	0.052 (3)	−0.008 (2)	0.027 (2)	−0.006 (2)
C10	0.038 (3)	0.062 (3)	0.053 (3)	−0.010 (2)	0.012 (2)	0.022 (3)
C11	0.049 (3)	0.044 (3)	0.075 (4)	0.007 (2)	0.033 (3)	0.003 (3)
C12	0.064 (3)	0.064 (4)	0.048 (3)	−0.002 (3)	0.030 (3)	0.001 (3)
C13	0.061 (3)	0.071 (4)	0.051 (3)	0.006 (3)	0.019 (3)	0.012 (3)
C14	0.046 (3)	0.051 (3)	0.067 (4)	0.008 (2)	0.018 (3)	0.006 (3)
N1	0.039 (2)	0.044 (2)	0.0305 (18)	−0.0094 (17)	0.0129 (15)	−0.0109 (16)
N2	0.059 (3)	0.068 (3)	0.049 (2)	−0.034 (2)	0.029 (2)	−0.029 (2)

Geometric parameters (Å, º) top

S1—C1	1.727 (5)	C5A—H5AB	0.9800
S1—C3	1.768 (5)	C5A—H5AC	0.9800
Cl1—C10	1.717 (5)	C6A—H6AA	0.9800
C1—N2	1.314 (6)	C6A—H6AB	0.9800
C1—N1	1.329 (6)	C6A—H6AC	0.9800
C2—C3	1.349 (6)	C7A—H7AA	0.9800
C2—N1	1.407 (6)	C7A—H7AB	0.9800
C2—C4	1.516 (6)	C7A—H7AC	0.9800
C3—C8	1.515 (7)	C8—C9	1.514 (7)
C4—C6A	1.33 (3)	C8—H8A	0.9900
C4—C5	1.502 (9)	C8—H8B	0.9900
C4—C7	1.525 (8)	C9—C14	1.369 (8)
C4—C6	1.568 (9)	C9—C10	1.403 (8)
C4—C7A	1.61 (3)	C10—C11	1.415 (8)
C4—C5A	1.64 (3)	C11—C12	1.349 (8)
C5—H5A	0.9800	C11—H11	0.9500
C5—H5B	0.9800	C12—C13	1.355 (8)
C5—H5C	0.9800	C12—H12	0.9500
C6—H6A	0.9800	C13—C14	1.353 (8)
C6—H6B	0.9800	C13—H13	0.9500
C6—H6C	0.9800	C14—H14	0.9500
C7—H7A	0.9800	N1—H1	0.8800
C7—H7B	0.9800	N2—H2A	0.8800
C7—H7C	0.9800	N2—H2B	0.8800
C5A—H5AA	0.9800

C1—S1—C3	90.8 (2)	C4—C5A—H5AB	109.5
N2—C1—N1	123.8 (4)	H5AA—C5A—H5AB	109.5
N2—C1—S1	125.4 (4)	C4—C5A—H5AC	109.5
N1—C1—S1	110.7 (3)	H5AA—C5A—H5AC	109.5
C3—C2—N1	111.7 (4)	H5AB—C5A—H5AC	109.5
C3—C2—C4	133.1 (4)	C4—C6A—H6AA	109.5
N1—C2—C4	115.2 (4)	C4—C6A—H6AB	109.5
C2—C3—C8	133.1 (5)	H6AA—C6A—H6AB	109.5
C2—C3—S1	110.9 (4)	C4—C6A—H6AC	109.5
C8—C3—S1	116.0 (4)	H6AA—C6A—H6AC	109.5
C6A—C4—C5	68 (2)	H6AB—C6A—H6AC	109.5
C6A—C4—C2	118.5 (18)	C4—C7A—H7AA	109.5
C5—C4—C2	111.0 (5)	C4—C7A—H7AB	109.5
C6A—C4—C7	124.1 (18)	H7AA—C7A—H7AB	109.5
C5—C4—C7	111.7 (6)	C4—C7A—H7AC	109.5
C2—C4—C7	113.4 (5)	H7AA—C7A—H7AC	109.5
C5—C4—C6	107.9 (7)	H7AB—C7A—H7AC	109.5
C2—C4—C6	107.5 (5)	C9—C8—C3	112.1 (4)
C7—C4—C6	104.9 (6)	C9—C8—H8A	109.2
C6A—C4—C7A	114 (2)	C3—C8—H8A	109.2
C5—C4—C7A	140.6 (19)	C9—C8—H8B	109.2
C2—C4—C7A	102.4 (17)	C3—C8—H8B	109.2
C6—C4—C7A	80.2 (17)	H8A—C8—H8B	107.9
C6A—C4—C5A	115 (2)	C14—C9—C10	116.6 (5)
C5—C4—C5A	51.9 (16)	C14—C9—C8	121.0 (5)
C2—C4—C5A	103.4 (16)	C10—C9—C8	122.4 (5)
C7—C4—C5A	69.0 (17)	C9—C10—C11	120.9 (5)
C6—C4—C5A	148.1 (16)	C9—C10—Cl1	119.5 (4)
C7A—C4—C5A	101 (2)	C11—C10—Cl1	119.6 (4)
C4—C5—H5A	109.5	C12—C11—C10	118.1 (5)
C4—C5—H5B	109.5	C12—C11—H11	121.0
H5A—C5—H5B	109.5	C10—C11—H11	121.0
C4—C5—H5C	109.5	C11—C12—C13	121.8 (5)
H5A—C5—H5C	109.5	C11—C12—H12	119.1
H5B—C5—H5C	109.5	C13—C12—H12	119.1
C4—C6—H6A	109.5	C14—C13—C12	120.0 (6)
C4—C6—H6B	109.5	C14—C13—H13	120.0
H6A—C6—H6B	109.5	C12—C13—H13	120.0
C4—C6—H6C	109.5	C13—C14—C9	122.7 (5)
H6A—C6—H6C	109.5	C13—C14—H14	118.7
H6B—C6—H6C	109.5	C9—C14—H14	118.7
C4—C7—H7A	109.5	C1—N1—C2	115.9 (4)
C4—C7—H7B	109.5	C1—N1—H1	122.1
H7A—C7—H7B	109.5	C2—N1—H1	122.1
C4—C7—H7C	109.5	C1—N2—H2A	120.0
H7A—C7—H7C	109.5	C1—N2—H2B	120.0
H7B—C7—H7C	109.5	H2A—N2—H2B	120.0
C4—C5A—H5AA	109.5

C3—S1—C1—N2	−177.2 (5)	C2—C3—C8—C9	−165.2 (6)
C3—S1—C1—N1	0.5 (4)	S1—C3—C8—C9	17.5 (7)
N1—C2—C3—C8	−177.7 (6)	C3—C8—C9—C14	−102.7 (6)
C4—C2—C3—C8	0.9 (11)	C3—C8—C9—C10	76.8 (7)
N1—C2—C3—S1	−0.3 (6)	C14—C9—C10—C11	1.9 (7)
C4—C2—C3—S1	178.3 (5)	C8—C9—C10—C11	−177.6 (5)
C1—S1—C3—C2	−0.1 (5)	C14—C9—C10—Cl1	−177.7 (4)
C1—S1—C3—C8	177.8 (5)	C8—C9—C10—Cl1	2.8 (7)
C3—C2—C4—C6A	−165 (2)	C9—C10—C11—C12	−0.4 (8)
N1—C2—C4—C6A	14 (2)	Cl1—C10—C11—C12	179.3 (4)
C3—C2—C4—C5	119.8 (8)	C10—C11—C12—C13	−1.5 (9)
N1—C2—C4—C5	−61.6 (7)	C11—C12—C13—C14	1.7 (9)
C3—C2—C4—C7	−6.8 (10)	C12—C13—C14—C9	0.0 (9)
N1—C2—C4—C7	171.7 (6)	C10—C9—C14—C13	−1.7 (8)
C3—C2—C4—C6	−122.3 (7)	C8—C9—C14—C13	177.8 (5)
N1—C2—C4—C6	56.2 (7)	N2—C1—N1—C2	177.0 (5)
C3—C2—C4—C7A	−38.8 (19)	S1—C1—N1—C2	−0.8 (6)
N1—C2—C4—C7A	139.8 (18)	C3—C2—N1—C1	0.7 (7)
C3—C2—C4—C5A	65.8 (19)	C4—C2—N1—C1	−178.2 (4)
N1—C2—C4—C5A	−115.6 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Br1ⁱ	0.88	2.36	3.232 (4)	169
N2—H2A···Br1	0.88	2.54	3.314 (4)	147
N1—H1···Br1	0.88	2.50	3.262 (4)	146

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈ClN₂S⁺·Br⁻
M_r	361.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.4439 (5), 14.5569 (8), 12.1926 (6)
β (°)	102.988 (1)
V (Å³)	1633.28 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.80
Crystal size (mm)	0.48 × 0.39 × 0.32

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.302, 0.407
No. of measured, independent and observed [I > 2σ(I)] reflections	10068, 3203, 2545
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.158, 1.05
No. of reflections	3203
No. of parameters	200
No. of restraints	117
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.10, −0.83

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Br1ⁱ	0.88	2.36	3.232 (4)	168.8
N2—H2A···Br1	0.88	2.54	3.314 (4)	146.9
N1—H1···Br1	0.88	2.50	3.262 (4)	145.6

Symmetry code: (i) x, −y+1/2, z+1/2.

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