Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018296/bt2340sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018296/bt2340Isup2.hkl |
CCDC reference: 647602
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
For related literature, see: He et al. (2006); Saïd El et et al. (2002); Xu et al. (2007).
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.
All H atoms with exception of the water H atoms were refined using a riding model with N—H distances of 0.88 A° and C— H distances ranging from 0.95to 0.99Å and with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(Cmethyl). The coordinates of the water H atoms were refined with an O—H distance restraint of 0.86 (1) Å, a H—H distance restraint of 1.38 (1) Å, and Uiso(H) = 1.2Ueq(O).
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.
For related literature, see: He et al. (2006); Saïd El et et al. (2002); Xu et al. (2007).
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.
Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids. |
C22H32N4S22+·2(Br−)·H2O | Z = 2 |
Mr = 594.47 | F(000) = 608 |
Triclinic, P1 | Dx = 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 |
Bruker SMART 1000 CCD diffractometer | 4962 independent reflections |
Radiation source: fine-focus sealed tube | 3929 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 26.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.248, Tmax = 0.590 | k = −12→12 |
9833 measured reflections | l = −19→19 |
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(Fo2) + (0.057P)2 + 1.5162P] where P = (Fo2 + 2Fc2)/3 |
4962 reflections | (Δ/σ)max = 0.001 |
292 parameters | Δρmax = 0.75 e Å−3 |
3 restraints | Δρmin = −0.43 e Å−3 |
C22H32N4S22+·2(Br−)·H2O | γ = 71.805 (1)° |
Mr = 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)° |
Bruker SMART 1000 CCD diffractometer | 4962 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3929 reflections with I > 2σ(I) |
Tmin = 0.248, Tmax = 0.590 | Rint = 0.024 |
9833 measured reflections |
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 | Δρmax = 0.75 e Å−3 |
4962 reflections | Δρmin = −0.43 e Å−3 |
292 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.248, 0.590 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9833, 4962, 3929 |
Rint | 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 |
Δρmax, Δρmin (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.
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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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.