6-Meth­yl-N-(3-oxo-1-thia-4-aza­spiro­[4.4]non-4-yl)imidazo[2,1-b][1,3]thia­zole-5-carboxamide monohydrate

The title compound, C₁₄H₁₆N₄O₂S₂·H₂O, is a member of a new series of imidazo[2,1-b]thia­zoles. The crystal packing is stabilized by inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.076
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

6-Methyl-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)imidazo[2,1-b][1,3]thiazole- 5-carboxamide monohydrate

Crystal data

C14H16N4O2S2·H2O	F(000) = 1488
Mr = 354.46	Dx = 1.400 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 338 reflections
a = 12.959 (5) Å	θ = 6.0–20.0°
b = 10.908 (5) Å	µ = 0.34 mm^−1
c = 23.797 (5) Å	T = 100 K
V = 3364 (2) Å^3	Prism, colourless
Z = 8	0.35 × 0.24 × 0.14 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	4118 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 9 pixels mm^-1	θmax = 28.5°, θmin = 3.4°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −14→14
Tmin = 0.891, Tmax = 0.955	l = −29→31
32544 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0323P)^2 + 1.4591P] where P = (Fo^2 + 2Fc^2)/3
4118 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.47312 (4)	0.72384 (3)	0.53705 (1)	0.0296 (1)
S2	0.62994 (3)	−0.04989 (3)	0.71710 (2)	0.0256 (1)
O1	0.62905 (8)	0.31537 (9)	0.62365 (4)	0.0229 (3)
O2	0.61153 (9)	0.03329 (10)	0.55917 (4)	0.0318 (3)
O3	0.35228 (9)	0.10205 (10)	0.53984 (4)	0.0245 (3)
N1	0.34127 (10)	0.53845 (11)	0.57934 (5)	0.0233 (4)
N2	0.51176 (9)	0.50768 (10)	0.57351 (4)	0.0182 (3)
N3	0.48705 (9)	0.18938 (10)	0.62017 (5)	0.0168 (3)
N4	0.54470 (9)	0.09398 (10)	0.64301 (4)	0.0171 (3)
C1	0.27995 (12)	0.34277 (14)	0.62162 (7)	0.0286 (5)
C2	0.36446 (11)	0.42210 (12)	0.59894 (6)	0.0206 (4)
C3	0.43119 (12)	0.58534 (12)	0.56448 (5)	0.0220 (4)
C4	0.59970 (14)	0.66950 (14)	0.53885 (6)	0.0291 (5)
C5	0.60822 (12)	0.55494 (13)	0.55886 (6)	0.0228 (4)
C6	0.46929 (11)	0.39983 (12)	0.59538 (5)	0.0171 (4)
C7	0.53737 (10)	0.29958 (11)	0.61324 (5)	0.0163 (3)
C8	0.60205 (11)	0.01971 (12)	0.60988 (6)	0.0221 (4)
C9	0.64814 (15)	−0.08377 (15)	0.64338 (7)	0.0324 (5)
C10	0.53538 (11)	0.07321 (11)	0.70366 (5)	0.0161 (4)
C11	0.42530 (11)	0.03973 (13)	0.72272 (6)	0.0219 (4)
C12	0.41831 (14)	0.08223 (16)	0.78454 (6)	0.0302 (5)
C13	0.52176 (13)	0.14569 (14)	0.79753 (6)	0.0261 (4)
C14	0.56245 (12)	0.18480 (12)	0.73989 (5)	0.0210 (4)
H1A	0.3052 (15)	0.2898 (16)	0.6527 (8)	0.0380*
H1B	0.2214 (15)	0.3942 (16)	0.6323 (8)	0.0380*
H1C	0.2572 (14)	0.2897 (16)	0.5926 (8)	0.0380*
H3	0.4388 (14)	0.1629 (16)	0.5950 (7)	0.0310*
H4	0.6507 (14)	0.7222 (16)	0.5269 (7)	0.0310*
H5	0.6653 (14)	0.5075 (16)	0.5643 (7)	0.0310*
H9A	0.6102 (13)	−0.1615 (17)	0.6319 (7)	0.0310*
H9B	0.7186 (15)	−0.0884 (15)	0.6367 (7)	0.0310*
H11A	0.3757 (13)	0.0873 (16)	0.6972 (7)	0.0310*
H11B	0.4108 (14)	−0.0484 (17)	0.7161 (7)	0.0310*
H12A	0.3607 (14)	0.1372 (16)	0.7894 (7)	0.0310*
H12B	0.4064 (13)	0.0166 (16)	0.8080 (8)	0.0310*
H13A	0.5147 (13)	0.2149 (16)	0.8240 (7)	0.0310*
H13B	0.5742 (14)	0.0916 (16)	0.8143 (7)	0.0310*
H14A	0.6366 (14)	0.2048 (15)	0.7387 (7)	0.0310*
H14B	0.5200 (13)	0.2584 (16)	0.7262 (7)	0.0310*
H31	0.3706 (15)	0.0553 (18)	0.5128 (9)	0.042 (6)*
H32	0.2979 (17)	0.0806 (19)	0.5512 (9)	0.044 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0495 (3)	0.0205 (2)	0.0189 (2)	0.0087 (2)	−0.0009 (2)	0.0051 (1)
S2	0.0266 (2)	0.0198 (2)	0.0304 (2)	0.0081 (1)	−0.0033 (2)	0.0043 (1)
O1	0.0168 (5)	0.0232 (5)	0.0288 (5)	0.0012 (4)	−0.0023 (4)	0.0054 (4)
O2	0.0398 (7)	0.0324 (6)	0.0233 (5)	0.0066 (5)	0.0123 (5)	−0.0038 (4)
O3	0.0221 (6)	0.0290 (5)	0.0223 (5)	−0.0104 (5)	0.0057 (4)	−0.0071 (4)
N1	0.0240 (7)	0.0234 (6)	0.0224 (6)	0.0086 (5)	−0.0079 (5)	−0.0063 (5)
N2	0.0233 (7)	0.0176 (5)	0.0138 (5)	0.0042 (5)	−0.0022 (4)	0.0002 (4)
N3	0.0178 (6)	0.0174 (5)	0.0153 (5)	0.0031 (4)	−0.0032 (4)	0.0001 (4)
N4	0.0195 (6)	0.0154 (5)	0.0163 (5)	0.0049 (4)	−0.0004 (4)	−0.0008 (4)
C1	0.0179 (8)	0.0257 (8)	0.0421 (9)	0.0013 (6)	−0.0005 (7)	−0.0089 (7)
C2	0.0212 (8)	0.0204 (6)	0.0201 (6)	0.0047 (5)	−0.0056 (5)	−0.0068 (5)
C3	0.0321 (9)	0.0200 (6)	0.0138 (6)	0.0085 (6)	−0.0063 (5)	−0.0017 (5)
C4	0.0400 (10)	0.0275 (7)	0.0197 (6)	−0.0016 (7)	0.0061 (6)	0.0052 (6)
C5	0.0276 (8)	0.0240 (7)	0.0169 (6)	0.0001 (6)	0.0032 (5)	0.0031 (5)
C6	0.0182 (7)	0.0178 (6)	0.0153 (6)	0.0007 (5)	−0.0028 (5)	−0.0011 (5)
C7	0.0164 (7)	0.0192 (6)	0.0134 (5)	0.0027 (5)	0.0006 (5)	0.0003 (5)
C8	0.0202 (8)	0.0201 (6)	0.0261 (7)	0.0016 (5)	0.0058 (6)	−0.0029 (5)
C9	0.0351 (10)	0.0269 (8)	0.0353 (8)	0.0132 (7)	0.0156 (7)	0.0028 (7)
C10	0.0180 (7)	0.0142 (6)	0.0161 (6)	0.0026 (5)	−0.0009 (5)	0.0019 (5)
C11	0.0203 (8)	0.0231 (7)	0.0223 (7)	−0.0007 (6)	0.0005 (6)	0.0048 (5)
C12	0.0348 (10)	0.0342 (8)	0.0217 (7)	0.0006 (7)	0.0085 (6)	0.0051 (6)
C13	0.0357 (9)	0.0273 (7)	0.0154 (6)	0.0044 (7)	−0.0016 (6)	0.0004 (6)
C14	0.0263 (8)	0.0190 (6)	0.0176 (6)	0.0004 (6)	−0.0027 (6)	−0.0013 (5)

Geometric parameters (Å, º)

S1—C3	1.7332 (16)	C8—C9	1.505 (2)
S1—C4	1.745 (2)	C10—C14	1.5323 (19)
S2—C9	1.8082 (19)	C10—C11	1.541 (2)
S2—C10	1.8458 (16)	C11—C12	1.545 (2)
O1—C7	1.2258 (17)	C12—C13	1.540 (3)
O2—C8	1.2220 (18)	C13—C14	1.530 (2)
O3—H31	0.86 (2)	C1—H1C	0.948 (18)
O3—H32	0.79 (2)	C1—H1B	0.977 (19)
N1—C2	1.3851 (19)	C1—H1A	0.994 (19)
N1—C3	1.321 (2)	C4—H4	0.921 (18)
N2—C5	1.396 (2)	C5—H5	0.912 (18)
N2—C3	1.3616 (19)	C9—H9A	1.018 (18)
N2—C6	1.3992 (18)	C9—H9B	0.928 (19)
N3—N4	1.3916 (17)	C11—H11A	1.025 (17)
N3—C7	1.3775 (18)	C11—H11B	0.992 (18)
N4—C10	1.4659 (17)	C12—H12B	0.921 (18)
N4—C8	1.3529 (19)	C12—H12A	0.965 (18)
N3—H3	0.913 (17)	C13—H13A	0.988 (17)
C1—C2	1.497 (2)	C13—H13B	0.985 (18)
C2—C6	1.383 (2)	C14—H14B	1.026 (17)
C4—C5	1.342 (2)	C14—H14A	0.986 (18)
C6—C7	1.4679 (19)
S1···C7^i	3.588 (2)	C8···O1	3.261 (2)
S1···O3^i	3.475 (2)	C9···O1^viii	3.125 (3)
S1···C6^i	3.508 (2)	C13···C3^iii	3.404 (2)
S2···N4	2.6060 (16)	C13···N2^iii	3.446 (2)
S1···H9A^ii	3.133 (17)	C14···O1	3.229 (2)
S2···H13B	2.873 (17)	C14···C7	3.280 (2)
S2···H14B^iii	3.157 (17)	C1···H3	2.914 (18)
O1···N2	2.852 (2)	C2···H32^ix	2.95 (2)
O1···N4	2.6905 (19)	C2···H13B^vii	2.883 (17)
O1···C5	3.046 (2)	C2···H3	2.988 (18)
O1···C8	3.261 (2)	C3···H13A^vii	3.087 (17)
O1···C14	3.229 (2)	C3···H32^ix	2.99 (2)
O1···C9^iv	3.125 (3)	C3···H13B^vii	2.886 (17)
O2···O3^v	2.8197 (19)	C4···H9A^ii	2.884 (18)
O2···N3	2.758 (2)	C6···H12B^vii	3.083 (18)
O2···C7	3.319 (2)	C6···H13B^vii	3.052 (17)
O3···C4^i	3.179 (2)	C7···H5	3.041 (18)
O3···S1^i	3.475 (2)	C7···H14B	2.735 (17)
O3···C1	3.400 (2)	C8···H31^v	3.05 (2)
O3···N1^vi	2.767 (2)	H1A···N3	2.712 (19)
O3···N3	2.759 (2)	H1C···O3	2.699 (18)
O3···O2^v	2.8197 (19)	H1C···H32	2.54 (3)
O1···H9B^iv	2.258 (19)	H3···O2	2.781 (18)
O1···H14B	2.888 (17)	H3···O3	1.850 (17)
O1···H5	2.571 (17)	H3···C1	2.914 (18)
O1···H12B^vii	2.770 (18)	H3···C2	2.988 (18)
O2···H5^viii	2.908 (18)	H3···H31	2.45 (3)
O2···H31^v	1.98 (2)	H3···H32	2.29 (3)
O2···H3	2.781 (18)	H4···O3^i	2.490 (17)
O3···H3	1.850 (17)	H5···O2^iv	2.908 (18)
O3···H4^i	2.490 (17)	H5···H9B^iv	2.52 (2)
O3···H1C	2.699 (18)	H5···C7	3.041 (18)
N1···O3^ix	2.767 (2)	H5···O1	2.571 (17)
N1···N2	2.239 (2)	H9A···S1^x	3.133 (17)
N2···O1	2.852 (2)	H9A···C4^x	2.884 (18)
N2···C13^vii	3.446 (2)	H9A···H13A^iii	2.35 (2)
N3···O3	2.759 (2)	H9B···O1^viii	2.258 (19)
N3···O2	2.758 (2)	H9B···H5^viii	2.52 (2)
N3···C1	3.163 (2)	H11A···N3	2.585 (17)
N4···O1	2.6905 (19)	H12B···O1^iii	2.770 (18)
N4···S2	2.6060 (16)	H12B···C6^iii	3.083 (18)
N1···H13B^vii	2.818 (17)	H13A···H9A^vii	2.35 (2)
N1···H32^ix	1.98 (2)	H13A···C3^iii	3.087 (17)
N3···H1A	2.712 (19)	H13B···S2	2.873 (17)
N3···H11A	2.585 (17)	H13B···C3^iii	2.886 (17)
N3···H14B	2.668 (17)	H13B···C6^iii	3.052 (17)
C1···O3	3.400 (2)	H13B···N1^iii	2.818 (17)
C1···N3	3.163 (2)	H13B···C2^iii	2.883 (17)
C2···C4^i	3.459 (3)	H14B···O1	2.888 (17)
C3···C13^vii	3.404 (2)	H14B···S2^vii	3.157 (17)
C3···C5^i	3.349 (2)	H14B···N3	2.668 (17)
C4···C2^i	3.459 (3)	H14B···C7	2.735 (17)
C4···C6^i	3.402 (2)	H31···H3	2.45 (3)
C4···O3^i	3.179 (2)	H31···O2^v	1.98 (2)
C5···C3^i	3.349 (2)	H31···C8^v	3.05 (2)
C5···O1	3.046 (2)	H32···H1C	2.54 (3)
C6···C4^i	3.402 (2)	H32···H3	2.29 (3)
C6···S1^i	3.508 (2)	H32···N1^vi	1.98 (2)
C7···C14	3.280 (2)	H32···C2^vi	2.95 (2)
C7···S1^i	3.588 (2)	H32···C3^vi	2.99 (2)
C7···O2	3.319 (2)
C3—S1—C4	89.39 (7)	C11—C12—C13	105.96 (12)
C9—S2—C10	93.85 (7)	C12—C13—C14	104.20 (12)
H31—O3—H32	109 (2)	C10—C14—C13	101.77 (11)
C2—N1—C3	104.69 (12)	C2—C1—H1A	111.3 (11)
C3—N2—C5	114.67 (11)	C2—C1—H1C	108.5 (11)
C3—N2—C6	106.27 (11)	H1A—C1—H1B	113.3 (16)
C5—N2—C6	139.06 (12)	C2—C1—H1B	109.3 (11)
N4—N3—C7	116.44 (11)	H1B—C1—H1C	107.4 (16)
N3—N4—C8	121.01 (10)	H1A—C1—H1C	106.8 (15)
N3—N4—C10	117.12 (10)	C5—C4—H4	129.2 (11)
C8—N4—C10	121.77 (11)	S1—C4—H4	117.1 (11)
C7—N3—H3	121.5 (11)	N2—C5—H5	118.8 (11)
N4—N3—H3	112.8 (11)	C4—C5—H5	130.2 (11)
N1—C2—C6	110.70 (12)	S2—C9—H9B	107.8 (10)
N1—C2—C1	119.50 (13)	C8—C9—H9A	106.9 (10)
C1—C2—C6	129.76 (13)	S2—C9—H9A	111.6 (10)
N1—C3—N2	113.16 (12)	H9A—C9—H9B	112.6 (14)
S1—C3—N2	111.18 (11)	C8—C9—H9B	109.9 (10)
S1—C3—N1	135.64 (12)	C10—C11—H11A	106.6 (10)
S1—C4—C5	113.73 (13)	C10—C11—H11B	111.0 (10)
N2—C5—C4	111.02 (14)	C12—C11—H11B	115.5 (10)
N2—C6—C2	105.16 (11)	H11A—C11—H11B	106.1 (14)
N2—C6—C7	119.84 (12)	C12—C11—H11A	112.1 (10)
C2—C6—C7	134.72 (12)	C11—C12—H12B	110.7 (12)
O1—C7—N3	123.87 (12)	C13—C12—H12A	111.7 (11)
N3—C7—C6	113.59 (11)	C13—C12—H12B	111.9 (11)
O1—C7—C6	122.44 (12)	H12A—C12—H12B	106.3 (15)
O2—C8—C9	125.03 (13)	C11—C12—H12A	110.3 (10)
N4—C8—C9	111.00 (12)	C12—C13—H13B	114.4 (10)
O2—C8—N4	123.93 (13)	C14—C13—H13A	113.0 (10)
S2—C9—C8	107.98 (11)	C12—C13—H13A	113.0 (10)
S2—C10—C14	109.17 (9)	H13A—C13—H13B	105.3 (14)
S2—C10—N4	103.20 (8)	C14—C13—H13B	107.0 (10)
C11—C10—C14	103.57 (11)	C10—C14—H14A	112.5 (10)
S2—C10—C11	113.03 (9)	C10—C14—H14B	108.7 (10)
N4—C10—C11	113.75 (11)	C13—C14—H14B	108.5 (9)
N4—C10—C14	114.35 (10)	H14A—C14—H14B	109.9 (14)
C10—C11—C12	105.27 (12)	C13—C14—H14A	115.1 (10)
C3—S1—C4—C5	−0.02 (12)	N3—N4—C10—S2	−175.64 (9)
C4—S1—C3—N2	0.17 (10)	C8—N4—C10—C14	126.50 (14)
C4—S1—C3—N1	178.87 (15)	C8—N4—C10—C11	−114.78 (14)
C9—S2—C10—C11	111.17 (10)	C10—N4—C8—O2	179.64 (13)
C9—S2—C10—C14	−134.14 (10)	N3—N4—C8—O2	3.5 (2)
C9—S2—C10—N4	−12.14 (10)	N3—N4—C10—C14	−57.19 (16)
C10—S2—C9—C8	13.87 (12)	N3—N4—C8—C9	−174.09 (12)
C2—N1—C3—N2	−0.52 (15)	C1—C2—C6—C7	−3.2 (3)
C2—N1—C3—S1	−179.20 (12)	C1—C2—C6—N2	−176.91 (14)
C3—N1—C2—C1	177.80 (13)	N1—C2—C6—C7	174.60 (13)
C3—N1—C2—C6	−0.26 (15)	N1—C2—C6—N2	0.89 (15)
C6—N2—C5—C4	179.73 (14)	S1—C4—C5—N2	−0.12 (17)
C6—N2—C3—N1	1.07 (14)	N2—C6—C7—N3	−164.32 (11)
C5—N2—C6—C7	4.5 (2)	C2—C6—C7—N3	22.7 (2)
C5—N2—C3—N1	−179.29 (11)	C2—C6—C7—O1	−153.75 (15)
C3—N2—C5—C4	0.26 (16)	N2—C6—C7—O1	19.25 (18)
C3—N2—C6—C7	−176.00 (11)	N4—C8—C9—S2	−11.53 (16)
C3—N2—C6—C2	−1.15 (13)	O2—C8—C9—S2	170.95 (13)
C5—N2—C6—C2	179.35 (14)	C11—C10—C14—C13	42.92 (13)
C6—N2—C3—S1	−179.91 (8)	N4—C10—C14—C13	167.26 (12)
C5—N2—C3—S1	−0.28 (13)	N4—C10—C11—C12	−153.44 (11)
N4—N3—C7—O1	3.27 (18)	S2—C10—C11—C12	89.30 (12)
C7—N3—N4—C8	−87.27 (15)	S2—C10—C14—C13	−77.74 (12)
N4—N3—C7—C6	−173.10 (10)	C14—C10—C11—C12	−28.71 (13)
C7—N3—N4—C10	96.40 (14)	C10—C11—C12—C13	3.50 (15)
C8—N4—C10—S2	8.05 (15)	C11—C12—C13—C14	23.08 (16)
C10—N4—C8—C9	2.08 (18)	C12—C13—C14—C10	−40.72 (14)
N3—N4—C10—C11	61.52 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.913 (17)	1.850 (17)	2.759 (2)	174.0 (17)
O3—H31···O2^v	0.86 (2)	1.98 (2)	2.8197 (19)	167.1 (19)
O3—H32···N1^vi	0.79 (2)	1.98 (2)	2.767 (2)	176 (2)

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