5,5′-(1,3-Phenyl­enedimethyl­ene)bis­(2-amino-4-tert-butyl­thia­zol-3-ium) dibromide monohydrate

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

doi:10.1107/S1600536807018296

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5,5′-(1,3-Phenylenedimethylene)bis(2-amino-4-tert-butylthiazol-3-ium) dibromide monohydrate

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

Geometric parameters of the title salt, C₂₂H₃₂N₄S₂²⁺·2Br⁻·H₂O, are in the usual ranges. The crystal packing is stabilized by N–H

O, N–H

Br and O–H

Br hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018296/bt2340sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018296/bt2340Isup2.hkl Contains datablock I

CCDC reference: 647602

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R factor = 0.030
wR factor = 0.112
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4A    ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Br

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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 2-aminothiazole group is a common functionality in medicinal chemistry. It is known to be a ligand of estrogen receptors, as well as a novel class of adenosine receptor antagonists. Some are also used as fungicide, inhibiting in vivo the growth of Xanthomonas, as an ingredient of herbicides or as schistosomicidal drugs (Saïd El et al., 2002). Two 2-aminothiazoles crystal structures were reported (He et al., 2006; Xu et al., 2007). We report here the synthesis and structure of the title 2-aminothiazoles derivative 5,5'-(1,3-phenylenebis(methylene))bis(2-amino-4-tert-butylthiazol-3-ium) dibromide monohydrate (I).

The molecular structure of (I) is illustrated in Fig.1. The dihedral angles between the central aromatic ring and the two thiazole rings are 76.7 (2) and 80.4 (2)°. The crystal packing is stabilized by N–H···O, N–H···Br and O–H···Br hydrogen bonds.

Related literature top

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

Experimental top

5,5'-(1,3-Phenylene)bis(2,2-dimethylpentan-3-one) (0.033 mol) was dissolved in 200 ml e thanol and the mixture was stirred and heated to reflux. Cupric bromide (0.132 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 (30 mL three times), then washed with water until the solution was neutral, dried over anhydrous sodium sulfate and concentrated in vacuo to give 5,5'-(1,3-phenylene)bis(4-bromo-2,2- dimethylpentan-3-one), yield 90.8%. Then a solution of thiourea (0.055 mol) and cupric bromide (0.028 mol) in ethanol (65 ml) was refluxed for 9 h. The solvent was evaporated and the precipitate formed was filtered off, dried, giving colourless crystals of (I), yield 63.2%. M.p. 463.6–464.5 K.

The crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

Structure description top

For related literature, see: He et al. (2006); Saïd El et 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.

5,5'-(1,3-Phenylenedimethylene)bis(2-amino-4-tert-butylthiazol-3-ium) dibromide monohydrate top

Crystal data top

C₂₂H₃₂N₄S₂²⁺·2(Br⁻)·H₂O	Z = 2
M_r = 594.47	F(000) = 608
Triclinic, P1	D_x = 1.517 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9104 (5) Å	Cell parameters from 4865 reflections
b = 9.9136 (5) Å	θ = 2.5–27.0°
c = 15.8574 (8) Å	µ = 3.30 mm⁻¹
α = 87.742 (1)°	T = 173 K
β = 78.019 (1)°	Block, colourless
γ = 71.805 (1)°	0.48 × 0.38 × 0.16 mm
V = 1301.24 (12) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	4962 independent reflections
Radiation source: fine-focus sealed tube	3929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.248, T_max = 0.590	k = −12→12
9833 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.057P)² + 1.5162P] where P = (F_o² + 2F_c²)/3
4962 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.75 e Å⁻³
3 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₃₂N₄S₂²⁺·2(Br⁻)·H₂O	γ = 71.805 (1)°
M_r = 594.47	V = 1301.24 (12) Å³
Triclinic, P1	Z = 2
a = 8.9104 (5) Å	Mo Kα radiation
b = 9.9136 (5) Å	µ = 3.30 mm⁻¹
c = 15.8574 (8) Å	T = 173 K
α = 87.742 (1)°	0.48 × 0.38 × 0.16 mm
β = 78.019 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4962 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3929 reflections with I > 2σ(I)
T_min = 0.248, T_max = 0.590	R_int = 0.024
9833 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	3 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.75 e Å⁻³
4962 reflections	Δρ_min = −0.43 e Å⁻³
292 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	0.25498 (5)	1.24569 (4)	1.18698 (2)	0.02619 (12)
Br2	0.55055 (6)	0.84294 (4)	0.39514 (3)	0.03703 (14)
S1	0.22272 (12)	0.85025 (10)	0.96410 (6)	0.0236 (2)
S2	0.44511 (11)	0.64652 (10)	0.72660 (6)	0.0206 (2)
C1	0.2366 (4)	0.9915 (4)	1.0193 (2)	0.0203 (8)
C2	0.1230 (4)	0.8691 (4)	1.1295 (2)	0.0186 (7)
C3	0.1364 (4)	0.7853 (4)	1.0620 (2)	0.0202 (8)
C4	0.0552 (4)	0.8669 (4)	1.2255 (2)	0.0221 (8)
C5	−0.0800 (5)	1.0070 (4)	1.2520 (3)	0.0324 (10)
H5A	−0.0359	1.0864	1.2405	0.049*
H5B	−0.1266	1.0067	1.3136	0.049*
H5C	−0.1640	1.0174	1.2187	0.049*
C6	0.1913 (5)	0.8533 (5)	1.2740 (3)	0.0364 (10)
H6A	0.2746	0.7612	1.2594	0.055*
H6B	0.1475	0.8603	1.3362	0.055*
H6C	0.2388	0.9297	1.2573	0.055*
C7	−0.0139 (6)	0.7448 (5)	1.2501 (3)	0.0336 (10)
H7A	−0.0946	0.7479	1.2158	0.050*
H7B	−0.0647	0.7538	1.3115	0.050*
H7C	0.0732	0.6543	1.2386	0.050*
C8	0.0896 (5)	0.6526 (4)	1.0542 (3)	0.0281 (9)
H8A	0.0995	0.5981	1.1075	0.034*
H8B	−0.0250	0.6808	1.0491	0.034*
C9	0.1919 (4)	0.5578 (4)	0.9776 (2)	0.0215 (8)
C10	0.1505 (4)	0.5771 (4)	0.8974 (2)	0.0200 (8)
H10	0.0555	0.6504	0.8908	0.024*
C11	0.2456 (4)	0.4908 (4)	0.8263 (2)	0.0182 (7)
C12	0.3822 (5)	0.3825 (4)	0.8373 (3)	0.0245 (8)
H12	0.4462	0.3210	0.7899	0.029*
C13	0.4262 (5)	0.3631 (4)	0.9168 (3)	0.0267 (9)
H13	0.5213	0.2898	0.9233	0.032*
C14	0.3320 (5)	0.4501 (4)	0.9872 (3)	0.0244 (8)
H14	0.3626	0.4365	1.0416	0.029*
C15	0.2030 (5)	0.5180 (4)	0.7381 (2)	0.0230 (8)
H15A	0.0853	0.5649	0.7452	0.028*
H15B	0.2305	0.4261	0.7069	0.028*
C16	0.2921 (4)	0.6108 (4)	0.6849 (2)	0.0193 (7)
C17	0.2797 (4)	0.6721 (4)	0.6087 (2)	0.0194 (7)
C18	0.4898 (4)	0.7414 (4)	0.6372 (2)	0.0211 (8)
C19	0.1713 (5)	0.6716 (4)	0.5460 (2)	0.0226 (8)
C20	0.0880 (6)	0.8264 (5)	0.5248 (3)	0.0393 (11)
H20A	0.0201	0.8782	0.5776	0.059*
H20B	0.0209	0.8277	0.4828	0.059*
H20C	0.1700	0.8717	0.5004	0.059*
C21	0.2753 (5)	0.5883 (5)	0.4639 (3)	0.0318 (9)
H21A	0.3551	0.6347	0.4371	0.048*
H21B	0.2064	0.5859	0.4236	0.048*
H21C	0.3311	0.4911	0.4785	0.048*
C22	0.0409 (5)	0.6038 (5)	0.5842 (3)	0.0368 (11)
H22A	0.0917	0.5035	0.5950	0.055*
H22B	−0.0304	0.6113	0.5437	0.055*
H22C	−0.0222	0.6532	0.6387	0.055*
N1	0.1818 (4)	0.9832 (3)	1.10288 (19)	0.0204 (6)
H1A	0.1822	1.0465	1.1402	0.024*
N2	0.2944 (4)	1.0916 (3)	0.9839 (2)	0.0284 (8)
H2A	0.2988	1.1597	1.0163	0.034*
H2B	0.3290	1.0906	0.9277	0.034*
N3	0.3936 (4)	0.7450 (3)	0.58320 (19)	0.0193 (6)
H3A	0.4003	0.7903	0.5344	0.023*
N4	0.6064 (4)	0.8003 (3)	0.6226 (2)	0.0269 (7)
H4A	0.6239	0.8455	0.5745	0.032*
H4B	0.6666	0.7943	0.6610	0.032*
O1W	0.4233 (4)	1.0337 (3)	0.80968 (19)	0.0356 (7)
H1B	0.432 (5)	1.054 (5)	0.7559 (10)	0.043*
H1C	0.513 (3)	0.971 (4)	0.814 (2)	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0306 (2)	0.0268 (2)	0.0245 (2)	−0.01054 (17)	−0.01016 (16)	−0.00086 (15)
Br2	0.0494 (3)	0.0318 (2)	0.0241 (2)	−0.0117 (2)	0.00306 (19)	0.00451 (17)
S1	0.0337 (5)	0.0247 (5)	0.0150 (4)	−0.0140 (4)	−0.0037 (4)	0.0005 (4)
S2	0.0254 (5)	0.0225 (4)	0.0181 (4)	−0.0113 (4)	−0.0083 (4)	0.0029 (3)
C1	0.0217 (19)	0.0184 (17)	0.0213 (19)	−0.0062 (15)	−0.0059 (15)	0.0018 (14)
C2	0.0203 (18)	0.0198 (17)	0.0158 (17)	−0.0053 (15)	−0.0052 (14)	−0.0011 (14)
C3	0.0233 (19)	0.0264 (19)	0.0134 (17)	−0.0107 (16)	−0.0053 (14)	0.0050 (14)
C4	0.024 (2)	0.028 (2)	0.0159 (18)	−0.0114 (16)	−0.0016 (15)	0.0003 (15)
C5	0.033 (2)	0.035 (2)	0.024 (2)	−0.0055 (19)	−0.0003 (17)	−0.0074 (17)
C6	0.033 (2)	0.059 (3)	0.020 (2)	−0.017 (2)	−0.0093 (18)	0.009 (2)
C7	0.049 (3)	0.037 (2)	0.018 (2)	−0.024 (2)	0.0030 (18)	−0.0007 (17)
C8	0.036 (2)	0.027 (2)	0.023 (2)	−0.0152 (18)	−0.0002 (17)	−0.0008 (16)
C9	0.025 (2)	0.0196 (18)	0.0246 (19)	−0.0163 (16)	−0.0022 (16)	0.0018 (15)
C10	0.0200 (18)	0.0158 (17)	0.0247 (19)	−0.0071 (15)	−0.0040 (15)	0.0030 (14)
C11	0.0250 (19)	0.0178 (17)	0.0157 (17)	−0.0124 (15)	−0.0047 (15)	0.0022 (13)
C12	0.025 (2)	0.0180 (18)	0.029 (2)	−0.0059 (16)	−0.0005 (16)	−0.0035 (15)
C13	0.027 (2)	0.0209 (19)	0.036 (2)	−0.0083 (16)	−0.0126 (18)	0.0084 (16)
C14	0.033 (2)	0.0241 (19)	0.025 (2)	−0.0180 (17)	−0.0120 (17)	0.0107 (16)
C15	0.028 (2)	0.0255 (19)	0.0192 (19)	−0.0127 (16)	−0.0061 (16)	0.0005 (15)
C16	0.0208 (18)	0.0202 (18)	0.0171 (17)	−0.0050 (15)	−0.0060 (14)	−0.0023 (14)
C17	0.0186 (18)	0.0173 (17)	0.0206 (18)	−0.0036 (14)	−0.0027 (15)	−0.0033 (14)
C18	0.0218 (19)	0.0186 (17)	0.0194 (18)	−0.0027 (15)	−0.0026 (15)	0.0011 (14)
C19	0.026 (2)	0.0261 (19)	0.0170 (18)	−0.0064 (16)	−0.0087 (15)	−0.0010 (15)
C20	0.044 (3)	0.029 (2)	0.038 (3)	0.006 (2)	−0.022 (2)	−0.0026 (19)
C21	0.033 (2)	0.035 (2)	0.026 (2)	−0.0091 (19)	−0.0047 (18)	−0.0092 (18)
C22	0.033 (2)	0.062 (3)	0.023 (2)	−0.021 (2)	−0.0126 (18)	0.001 (2)
N1	0.0249 (16)	0.0202 (15)	0.0178 (15)	−0.0091 (13)	−0.0041 (13)	−0.0023 (12)
N2	0.039 (2)	0.0273 (17)	0.0233 (17)	−0.0194 (16)	−0.0014 (15)	0.0008 (14)
N3	0.0250 (16)	0.0194 (15)	0.0151 (15)	−0.0075 (13)	−0.0072 (13)	0.0025 (12)
N4	0.0320 (19)	0.0346 (19)	0.0218 (17)	−0.0197 (16)	−0.0089 (14)	0.0063 (14)
O1W	0.0374 (18)	0.0344 (17)	0.0258 (15)	−0.0018 (14)	−0.0016 (13)	0.0029 (13)

Geometric parameters (Å, º) top

S1—C1	1.730 (4)	C12—H12	0.9500
S1—C3	1.775 (4)	C13—C14	1.389 (6)
S2—C18	1.717 (4)	C13—H13	0.9500
S2—C16	1.765 (4)	C14—H14	0.9500
C1—N2	1.312 (5)	C15—C16	1.518 (5)
C1—N1	1.322 (5)	C15—H15A	0.9900
C2—C3	1.344 (5)	C15—H15B	0.9900
C2—N1	1.406 (5)	C16—C17	1.341 (5)
C2—C4	1.519 (5)	C17—N3	1.407 (5)
C3—C8	1.515 (5)	C17—C19	1.524 (5)
C4—C7	1.524 (5)	C18—N4	1.320 (5)
C4—C5	1.532 (5)	C18—N3	1.324 (5)
C4—C6	1.535 (6)	C19—C22	1.527 (6)
C5—H5A	0.9800	C19—C21	1.530 (5)
C5—H5B	0.9800	C19—C20	1.540 (5)
C5—H5C	0.9800	C20—H20A	0.9800
C6—H6A	0.9800	C20—H20B	0.9800
C6—H6B	0.9800	C20—H20C	0.9800
C6—H6C	0.9800	C21—H21A	0.9800
C7—H7A	0.9800	C21—H21B	0.9800
C7—H7B	0.9800	C21—H21C	0.9800
C7—H7C	0.9800	C22—H22A	0.9800
C8—C9	1.511 (5)	C22—H22B	0.9800
C8—H8A	0.9900	C22—H22C	0.9800
C8—H8B	0.9900	N1—H1A	0.8800
C9—C10	1.386 (5)	N2—H2A	0.8800
C9—C14	1.398 (5)	N2—H2B	0.8800
C10—C11	1.395 (5)	N3—H3A	0.8800
C10—H10	0.9500	N4—H4A	0.8800
C11—C12	1.387 (5)	N4—H4B	0.8800
C11—C15	1.517 (5)	O1W—H1B	0.860 (10)
C12—C13	1.386 (6)	O1W—H1C	0.86 (3)

C1—S1—C3	90.67 (17)	C13—C14—C9	119.7 (4)
C18—S2—C16	90.78 (18)	C13—C14—H14	120.2
N2—C1—N1	124.8 (3)	C9—C14—H14	120.2
N2—C1—S1	125.2 (3)	C11—C15—C16	112.0 (3)
N1—C1—S1	110.0 (3)	C11—C15—H15A	109.2
C3—C2—N1	111.1 (3)	C16—C15—H15A	109.2
C3—C2—C4	133.6 (3)	C11—C15—H15B	109.2
N1—C2—C4	115.3 (3)	C16—C15—H15B	109.2
C2—C3—C8	132.8 (3)	H15A—C15—H15B	107.9
C2—C3—S1	111.1 (3)	C17—C16—C15	132.2 (3)
C8—C3—S1	116.1 (3)	C17—C16—S2	110.9 (3)
C2—C4—C7	113.0 (3)	C15—C16—S2	116.9 (3)
C2—C4—C5	108.3 (3)	C16—C17—N3	111.6 (3)
C7—C4—C5	108.4 (3)	C16—C17—C19	131.8 (3)
C2—C4—C6	108.4 (3)	N3—C17—C19	116.6 (3)
C7—C4—C6	108.8 (3)	N4—C18—N3	124.1 (3)
C5—C4—C6	109.8 (3)	N4—C18—S2	125.1 (3)
C4—C5—H5A	109.5	N3—C18—S2	110.8 (3)
C4—C5—H5B	109.5	C17—C19—C22	112.0 (3)
H5A—C5—H5B	109.5	C17—C19—C21	108.8 (3)
C4—C5—H5C	109.5	C22—C19—C21	109.0 (3)
H5A—C5—H5C	109.5	C17—C19—C20	108.5 (3)
H5B—C5—H5C	109.5	C22—C19—C20	108.4 (4)
C4—C6—H6A	109.5	C21—C19—C20	110.2 (3)
C4—C6—H6B	109.5	C19—C20—H20A	109.5
H6A—C6—H6B	109.5	C19—C20—H20B	109.5
C4—C6—H6C	109.5	H20A—C20—H20B	109.5
H6A—C6—H6C	109.5	C19—C20—H20C	109.5
H6B—C6—H6C	109.5	H20A—C20—H20C	109.5
C4—C7—H7A	109.5	H20B—C20—H20C	109.5
C4—C7—H7B	109.5	C19—C21—H21A	109.5
H7A—C7—H7B	109.5	C19—C21—H21B	109.5
C4—C7—H7C	109.5	H21A—C21—H21B	109.5
H7A—C7—H7C	109.5	C19—C21—H21C	109.5
H7B—C7—H7C	109.5	H21A—C21—H21C	109.5
C9—C8—C3	113.2 (3)	H21B—C21—H21C	109.5
C9—C8—H8A	108.9	C19—C22—H22A	109.5
C3—C8—H8A	108.9	C19—C22—H22B	109.5
C9—C8—H8B	108.9	H22A—C22—H22B	109.5
C3—C8—H8B	108.9	C19—C22—H22C	109.5
H8A—C8—H8B	107.8	H22A—C22—H22C	109.5
C10—C9—C14	119.3 (3)	H22B—C22—H22C	109.5
C10—C9—C8	121.1 (3)	C1—N1—C2	117.1 (3)
C14—C9—C8	119.7 (4)	C1—N1—H1A	121.4
C9—C10—C11	121.3 (3)	C2—N1—H1A	121.4
C9—C10—H10	119.4	C1—N2—H2A	120.0
C11—C10—H10	119.4	C1—N2—H2B	120.0
C12—C11—C10	118.8 (3)	H2A—N2—H2B	120.0
C12—C11—C15	120.6 (3)	C18—N3—C17	115.9 (3)
C10—C11—C15	120.6 (3)	C18—N3—H3A	122.0
C13—C12—C11	120.5 (4)	C17—N3—H3A	122.0
C13—C12—H12	119.7	C18—N4—H4A	120.0
C11—C12—H12	119.7	C18—N4—H4B	120.0
C12—C13—C14	120.4 (4)	H4A—N4—H4B	120.0
C12—C13—H13	119.8	H1B—O1W—H1C	106 (4)
C14—C13—H13	119.8

C3—S1—C1—N2	−179.9 (4)	C8—C9—C14—C13	−179.9 (3)
C3—S1—C1—N1	0.8 (3)	C12—C11—C15—C16	−84.1 (4)
N1—C2—C3—C8	−178.6 (4)	C10—C11—C15—C16	94.0 (4)
C4—C2—C3—C8	−0.3 (8)	C11—C15—C16—C17	−172.4 (4)
N1—C2—C3—S1	−0.2 (4)	C11—C15—C16—S2	9.0 (4)
C4—C2—C3—S1	178.0 (3)	C18—S2—C16—C17	−1.1 (3)
C1—S1—C3—C2	−0.3 (3)	C18—S2—C16—C15	177.8 (3)
C1—S1—C3—C8	178.4 (3)	C15—C16—C17—N3	−177.7 (4)
C3—C2—C4—C7	−0.9 (6)	S2—C16—C17—N3	0.9 (4)
N1—C2—C4—C7	177.3 (3)	C15—C16—C17—C19	−0.1 (7)
C3—C2—C4—C5	−121.0 (5)	S2—C16—C17—C19	178.6 (3)
N1—C2—C4—C5	57.2 (4)	C16—S2—C18—N4	−177.6 (3)
C3—C2—C4—C6	119.9 (5)	C16—S2—C18—N3	1.0 (3)
N1—C2—C4—C6	−61.9 (4)	C16—C17—C19—C22	8.7 (6)
C2—C3—C8—C9	−153.1 (4)	N3—C17—C19—C22	−173.8 (3)
S1—C3—C8—C9	28.6 (5)	C16—C17—C19—C21	−111.9 (4)
C3—C8—C9—C10	−88.1 (4)	N3—C17—C19—C21	65.6 (4)
C3—C8—C9—C14	91.0 (4)	C16—C17—C19—C20	128.3 (4)
C14—C9—C10—C11	0.2 (5)	N3—C17—C19—C20	−54.2 (4)
C8—C9—C10—C11	179.3 (3)	N2—C1—N1—C2	179.5 (4)
C9—C10—C11—C12	1.2 (5)	S1—C1—N1—C2	−1.1 (4)
C9—C10—C11—C15	−176.9 (3)	C3—C2—N1—C1	0.9 (5)
C10—C11—C12—C13	−2.0 (5)	C4—C2—N1—C1	−177.7 (3)
C15—C11—C12—C13	176.2 (3)	N4—C18—N3—C17	178.0 (3)
C11—C12—C13—C14	1.4 (6)	S2—C18—N3—C17	−0.6 (4)
C12—C13—C14—C9	0.0 (6)	C16—C17—N3—C18	−0.2 (4)
C10—C9—C14—C13	−0.8 (5)	C19—C17—N3—C18	−178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.88	2.45	3.266 (3)	155
N2—H2A···Br1	0.88	2.78	3.523 (3)	143
N2—H2B···O1W	0.88	1.91	2.770 (4)	164
N3—H3A···Br2	0.88	2.46	3.268 (3)	153
N4—H4B···Br1ⁱ	0.88	2.63	3.456 (3)	157
O1W—H1B···Br2ⁱⁱ	0.86 (1)	2.56 (1)	3.413 (3)	170 (4)
O1W—H1C···Br1ⁱ	0.86 (3)	2.47 (4)	3.315 (3)	167 (4)

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

Experimental details

Crystal data
Chemical formula	C₂₂H₃₂N₄S₂²⁺·2(Br⁻)·H₂O
M_r	594.47
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.9104 (5), 9.9136 (5), 15.8574 (8)
α, β, γ (°)	87.742 (1), 78.019 (1), 71.805 (1)
V (Å³)	1301.24 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.30
Crystal size (mm)	0.48 × 0.38 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.248, 0.590
No. of measured, independent and observed [I > 2σ(I)] reflections	9833, 4962, 3929
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.112, 1.10
No. of reflections	4962
No. of parameters	292
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.43

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
N1—H1A···Br1	0.88	2.45	3.266 (3)	155.1
N2—H2A···Br1	0.88	2.78	3.523 (3)	142.8
N2—H2B···O1W	0.88	1.91	2.770 (4)	164.4
N3—H3A···Br2	0.88	2.46	3.268 (3)	152.7
N4—H4B···Br1ⁱ	0.88	2.63	3.456 (3)	156.9
O1W—H1B···Br2ⁱⁱ	0.860 (10)	2.563 (13)	3.413 (3)	170 (4)
O1W—H1C···Br1ⁱ	0.86 (3)	2.47 (4)	3.315 (3)	167 (4)

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

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