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The structure of the title compound, C7H5N3O2S·H2O, comprises mol­ecules of the thia­zole in an extensive hydrogen-bonding network with lattice water molecules. The essentially planar thia­zole forms centrosymmetric, hydrogen-bonded dimers via a pair of N—H...N (H...N 2.11 Å) associations. The second amino H atom hydrogen bonds to the water O atom, while the water associates to one nitro O atom and two other water molecules. Complexity in the hydrogen-bonding network arises because the water mol­ecule is close to an inversion centre, thus producing an Ow...Ow interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016938/lh6001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016938/lh6001Isup2.hkl
Contains datablock I

CCDC reference: 198971

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.105
  • Data-to-parameter ratio = 11.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

A multitude of crystal structures of 2-aminobenzo-1,3-thiazole, and its derivatives, have been determined and provide an interesting subset of compounds in the 2-amino-1,3-thiazole range. Of the structures reported, most are pure organics that have fragments attached to the amino N atom. The structure of 2-aminobenzo-1,3-thiazole itself is unknown, but of the ring-substituted compounds, the structures of the 6-fluoro (Jai-nhuknan et al., 1997), and both 4-nitro (Lokaj et al., 1996) and 6-nitro (Glidewell et al., 2001) analogues have been determined. In these three cases, the recorded hydrogen-bonding patterns are noteworthy, as well as the bond distances in the two nitro derivatives. In 2-amino-4-nitrobenzo-1,3-thiazole, the C2—N21 and C2—N3 distances are equal to within 2σ [1.315 (2) and 1.312 (2) Å, respectively], a feature indicating complete π-electron delocalization. The bond distances in 2-amino-6-nitrobenzo-1,3-thiazole are less equal [1.331 (3) and 1.321 (3) Å], whereas for 2-amino-6-fluorobenzo-1,3-thiazole [1.358 (2) and 1.295 (2) Å] the bond distances are more acentric than the average values [1.336 (17) and 1.313 (11) Å; Allen et al., 1987]. The hydrogen-bonding patterns in all three structures includes a dimer formation about the N21—H···N3 association and for both nitro analogues at least one nitro O atom is also involved in the hydrogen-bonding array. In this paper, the single-crystal structure of 2-amino-6-nitrobenzo-1,3-thiazole hydrate, (I), is reported as an addition to the non-hydrate structure. The hydrate structure was obtained from attempts to produce adducts of 2-amino-6-nitrobenzo-1,3-thiazole with aromatic carboxylic acids, as done for 2-aminobenzo-1,3-thiazole (Lynch et al., 1998, 1999).

The structure of (I) (Fig. 1) comprises the thiazole molecule associated in an extensive hydrogen-bonded network with the water molecule. Hydrogen-bonding geometries are listed in Table 2. The bond lengths across the N21—C2—N3 site show a similar pattern as in the 4-nitro analogue, with both bond lengths being equal [1.320 (3) Å]. The formation of dimers via the N21—H···N3 association is expected for these types of compounds, but the location of the water molecule so near to a symmetry element provides an interesting hydrogen-bonding network (Fig. 2). The water network extends parallel to the a axis, while the thiazoles are inclined to the (100) plane. The water O atom is bound by the second amino H atom, while H1W associates to a nitroO atom. The suggested position of H2W allows for a three-centre association, linking two symmetry-generated water molecules.

Experimental top

Crystals of the title compound were separated from a partially evaporated ethanol solution containing an equimolar amount of 3-aminobenzoic acid.

Refinement top

All thiazole H atoms were included in the refinement, at calculated positions, as riding models, with C—H set to 0.95 Å and N—H set to 0.88 Å. H1W was initially located on difference syntheses, while H2W was generated at the most probable position based on the position of H1W and the position of adjacent symmetry-generated water molecules. Both H1W and H2W were restrained to an O—H distance of 0.83 Å and an H···H distance of 1.35 Å, while displacement parameters were refined as riding models.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram for the title compound. Hydrogen-bonding associations are shown as dotted lines.
2-Amino-6-nitrobenzo-1,3-thiazole hydrate top
Crystal data top
C7H5N3O2S·H2OF(000) = 440
Mr = 213.22Dx = 1.621 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5386 reflections
a = 3.8930 (2) Åθ = 2.9–32.0°
b = 10.8743 (5) ŵ = 0.35 mm1
c = 20.6378 (8) ÅT = 150 K
β = 91.335 (4)°Block, yellow
V = 873.44 (7) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
1504 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode1247 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 9.091 pixels mm-1θmax = 25.0°, θmin = 3.5°
ϕ and ω scansh = 44
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1212
Tmin = 0.933, Tmax = 0.970l = 2024
5105 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.3321P]
where P = (Fo2 + 2Fc2)/3
1504 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.32 e Å3
2 restraintsΔρmin = 0.25 e Å3
Crystal data top
C7H5N3O2S·H2OV = 873.44 (7) Å3
Mr = 213.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 3.8930 (2) ŵ = 0.35 mm1
b = 10.8743 (5) ÅT = 150 K
c = 20.6378 (8) Å0.20 × 0.15 × 0.10 mm
β = 91.335 (4)°
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
1504 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
1247 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.970Rint = 0.037
5105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0392 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.14Δρmax = 0.32 e Å3
1504 reflectionsΔρmin = 0.25 e Å3
133 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.04243 (15)0.76601 (5)0.09002 (3)0.0302 (2)
C20.2356 (5)0.64834 (19)0.04280 (10)0.0278 (5)
N210.3748 (5)0.67345 (17)0.01460 (9)0.0339 (5)
H210.47290.61460.03770.042*
H220.36950.74900.02980.042*
N30.2317 (5)0.53787 (16)0.06927 (9)0.0284 (5)
C40.0054 (6)0.4381 (2)0.16807 (11)0.0302 (5)
H40.08530.35910.15500.038*
C50.1677 (6)0.4525 (2)0.22604 (11)0.0301 (5)
H50.20850.38330.25330.038*
C60.2843 (6)0.56838 (19)0.24521 (10)0.0273 (5)
N610.4724 (5)0.58028 (17)0.30589 (9)0.0322 (5)
O610.5502 (5)0.48605 (15)0.33659 (8)0.0417 (5)
O620.5517 (5)0.68351 (15)0.32564 (8)0.0439 (5)
C70.2336 (5)0.67269 (19)0.20707 (10)0.0274 (5)
H70.31540.75110.22060.034*
C80.0599 (5)0.65679 (19)0.14898 (10)0.0260 (5)
C90.0638 (6)0.5403 (2)0.12820 (11)0.0262 (5)
O1W0.2649 (10)0.0608 (2)0.03261 (11)0.1058 (12)
H1W0.3060.0400.07090.132*
H2W0.2210.0090.00530.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0355 (4)0.0179 (3)0.0371 (4)0.0024 (2)0.0021 (3)0.0003 (2)
C20.0273 (12)0.0211 (12)0.0353 (13)0.0017 (9)0.0043 (9)0.0047 (9)
N210.0433 (12)0.0199 (10)0.0382 (12)0.0002 (9)0.0036 (9)0.0029 (8)
N30.0273 (11)0.0206 (10)0.0376 (11)0.0008 (8)0.0048 (8)0.0028 (8)
C40.0299 (13)0.0168 (11)0.0441 (14)0.0021 (9)0.0060 (10)0.0015 (9)
C50.0318 (13)0.0173 (11)0.0413 (14)0.0018 (9)0.0055 (10)0.0030 (9)
C60.0235 (12)0.0248 (12)0.0340 (13)0.0019 (9)0.0057 (9)0.0003 (9)
N610.0316 (11)0.0247 (11)0.0404 (12)0.0015 (9)0.0029 (8)0.0002 (8)
O610.0582 (12)0.0261 (9)0.0406 (10)0.0036 (8)0.0046 (8)0.0067 (7)
O620.0571 (12)0.0253 (9)0.0487 (11)0.0038 (8)0.0135 (8)0.0025 (8)
C70.0252 (12)0.0181 (11)0.0388 (13)0.0010 (9)0.0040 (9)0.0025 (9)
C80.0241 (12)0.0169 (11)0.0371 (13)0.0008 (9)0.0056 (9)0.0011 (9)
C90.0217 (11)0.0218 (11)0.0351 (13)0.0001 (9)0.0046 (9)0.0031 (9)
O1W0.223 (4)0.0400 (14)0.0523 (15)0.0334 (17)0.0421 (19)0.0132 (10)
Geometric parameters (Å, º) top
S1—C81.740 (2)C5—H50.95
S1—C21.766 (2)C6—C71.392 (3)
C2—N31.320 (3)C6—N611.442 (3)
C2—N211.320 (3)N61—O621.231 (2)
N21—H210.88N61—O611.239 (2)
N21—H220.88C7—C81.373 (3)
N3—C91.367 (3)C7—H70.95
C4—C51.368 (3)C8—C91.418 (3)
C4—C91.399 (3)O1W—H1W0.84
C4—H40.95O1W—H2W0.81
C5—C61.394 (3)
C8—S1—C288.80 (10)C7—C6—N61118.72 (19)
N3—C2—N21124.1 (2)C5—C6—N61118.90 (19)
N3—C2—S1115.50 (17)O62—N61—O61121.9 (2)
N21—C2—S1120.40 (16)O62—N61—C6119.20 (18)
C2—N21—H21120.0O61—N61—C6118.91 (18)
C2—N21—H22120.0C8—C7—C6116.8 (2)
H21—N21—H22120.0C8—C7—H7121.6
C2—N3—C9110.56 (18)C6—C7—H7121.6
C5—C4—C9119.6 (2)C7—C8—C9122.23 (19)
C5—C4—H4120.2C7—C8—S1128.65 (17)
C9—C4—H4120.2C9—C8—S1109.12 (16)
C4—C5—C6120.2 (2)N3—C9—C4125.2 (2)
C4—C5—H5119.9N3—C9—C8115.99 (19)
C6—C5—H5119.9C4—C9—C8118.9 (2)
C7—C6—C5122.4 (2)H1W—O1W—H2W120
C8—S1—C2—N31.44 (17)C6—C7—C8—C90.0 (3)
C8—S1—C2—N21179.22 (19)C6—C7—C8—S1179.32 (16)
N21—C2—N3—C9178.79 (19)C2—S1—C8—C7178.9 (2)
S1—C2—N3—C91.9 (2)C2—S1—C8—C90.53 (15)
C9—C4—C5—C60.1 (3)C2—N3—C9—C4178.1 (2)
C4—C5—C6—C70.4 (3)C2—N3—C9—C81.5 (3)
C4—C5—C6—N61178.67 (19)C5—C4—C9—N3179.75 (19)
C7—C6—N61—O627.6 (3)C5—C4—C9—C80.2 (3)
C5—C6—N61—O62174.1 (2)C7—C8—C9—N3179.88 (19)
C7—C6—N61—O61172.27 (19)S1—C8—C9—N30.4 (2)
C5—C6—N61—O616.0 (3)C7—C8—C9—C40.3 (3)
C5—C6—C7—C80.3 (3)S1—C8—C9—C4179.16 (16)
N61—C6—C7—C8178.58 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.882.112.970 (3)165
N21—H22···O1Wii0.882.112.946 (3)159
O1W—H1W···O61iii0.842.062.894 (3)175
O1W—H2W···O1Wiv0.812.172.772 (6)132
O1W—H2W···O1Wv0.812.302.651 (8)107
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z; (iii) x+1, y1/2, z+1/2; (iv) x, y, z; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC7H5N3O2S·H2O
Mr213.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)3.8930 (2), 10.8743 (5), 20.6378 (8)
β (°) 91.335 (4)
V3)873.44 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker–Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.933, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
5105, 1504, 1247
Rint0.037
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.105, 1.14
No. of reflections1504
No. of parameters133
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.25

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Selected bond lengths (Å) top
S1—C81.740 (2)C2—N31.320 (3)
S1—C21.766 (2)C2—N211.320 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.882.112.970 (3)165
N21—H22···O1Wii0.882.112.946 (3)159
O1W—H1W···O61iii0.842.062.894 (3)175
O1W—H2W···O1Wiv0.812.172.772 (6)132
O1W—H2W···O1Wv0.812.302.651 (8)107
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z; (iii) x+1, y1/2, z+1/2; (iv) x, y, z; (v) x+1, y, z.
 

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