The title compound, C10H12N4OS·H2O, was obtained from 6-methylimidazo[2,1-b]thiazole-5-carbohydrazide and 2-propanone. The crystal structure is stabilized by intra- and intermolecular hydrogen-bond interactions.
Supporting information
CCDC reference: 269560
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.107
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
6-Methyl-
N'-(1-methylethylidene)imidazo[2,1-
b][1,3]thiazole-5-carbohydrazide monohydrate
top
Crystal data top
C10H12N4OS·H2O | F(000) = 536 |
Mr = 254.32 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 15184 reflections |
a = 10.0955 (7) Å | θ = 2.2–27.3° |
b = 9.8500 (6) Å | µ = 0.26 mm−1 |
c = 13.3756 (8) Å | T = 293 K |
β = 111.226 (5)° | Plate, pale yellow |
V = 1239.85 (14) Å3 | 0.38 × 0.24 × 0.08 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 2771 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2217 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.3°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.908, Tmax = 0.980 | l = −17→17 |
15514 measured reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2624P] where P = (Fo2 + 2Fc2)/3 |
2771 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.59015 (5) | 0.08917 (5) | 0.11281 (4) | 0.0509 (2) | |
O1 | 0.96493 (14) | 0.48573 (13) | 0.17495 (12) | 0.0507 (4) | |
N1 | 0.76703 (16) | 0.10191 (15) | −0.00967 (12) | 0.0427 (4) | |
N2 | 0.79432 (14) | 0.24803 (14) | 0.12330 (11) | 0.0351 (4) | |
N3 | 1.11971 (16) | 0.38670 (15) | 0.10899 (12) | 0.0391 (4) | |
N4 | 1.22016 (15) | 0.48839 (14) | 0.15339 (12) | 0.0411 (4) | |
C1 | 0.9522 (2) | 0.1793 (2) | −0.07879 (15) | 0.0482 (6) | |
C2 | 0.87804 (18) | 0.18860 (16) | −0.00035 (13) | 0.0375 (5) | |
C3 | 0.72089 (18) | 0.14103 (17) | 0.06647 (13) | 0.0385 (5) | |
C4 | 0.6426 (2) | 0.2149 (2) | 0.20978 (17) | 0.0510 (6) | |
C5 | 0.75030 (19) | 0.29057 (19) | 0.20577 (15) | 0.0431 (5) | |
C6 | 0.89932 (17) | 0.27927 (16) | 0.08240 (13) | 0.0349 (5) | |
C7 | 0.99670 (17) | 0.39293 (16) | 0.12722 (13) | 0.0355 (5) | |
C8 | 1.32008 (18) | 0.49642 (17) | 0.11652 (14) | 0.0417 (5) | |
C9 | 1.4316 (2) | 0.6011 (2) | 0.1661 (2) | 0.0667 (8) | |
C10 | 1.3341 (2) | 0.4123 (2) | 0.02807 (17) | 0.0524 (6) | |
O2 | 0.27396 (16) | 0.13305 (14) | 0.14617 (13) | 0.0518 (5) | |
H1A | 0.98100 | 0.26840 | −0.09190 | 0.0720* | |
H1B | 0.88880 | 0.14140 | −0.14490 | 0.0720* | |
H1C | 1.03440 | 0.12230 | −0.05000 | 0.0720* | |
H3 | 1.146 (2) | 0.309 (2) | 0.1008 (19) | 0.056 (6)* | |
H4 | 0.589 (3) | 0.223 (2) | 0.258 (2) | 0.071 (7)* | |
H5 | 0.800 (2) | 0.366 (2) | 0.2505 (17) | 0.046 (5)* | |
H9A | 1.40840 | 0.65070 | 0.21930 | 0.1000* | |
H9B | 1.43610 | 0.66250 | 0.11160 | 0.1000* | |
H9C | 1.52200 | 0.55740 | 0.19910 | 0.1000* | |
H10A | 1.36870 | 0.32370 | 0.05500 | 0.0790* | |
H10B | 1.39960 | 0.45500 | 0.00090 | 0.0790* | |
H10C | 1.24300 | 0.40400 | −0.02850 | 0.0790* | |
H2A | 0.268 (3) | 0.055 (3) | 0.108 (2) | 0.074 (7)* | |
H2B | 0.291 (3) | 0.098 (3) | 0.206 (3) | 0.086 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0482 (3) | 0.0513 (3) | 0.0616 (3) | −0.0116 (2) | 0.0300 (2) | −0.0020 (2) |
O1 | 0.0501 (7) | 0.0455 (7) | 0.0661 (8) | −0.0052 (6) | 0.0327 (7) | −0.0171 (6) |
N1 | 0.0454 (8) | 0.0413 (7) | 0.0445 (8) | −0.0056 (6) | 0.0200 (7) | −0.0058 (6) |
N2 | 0.0352 (7) | 0.0366 (7) | 0.0376 (7) | 0.0007 (5) | 0.0180 (6) | 0.0003 (5) |
N3 | 0.0382 (7) | 0.0366 (7) | 0.0479 (8) | −0.0051 (6) | 0.0220 (6) | −0.0071 (6) |
N4 | 0.0405 (7) | 0.0389 (7) | 0.0464 (8) | −0.0076 (6) | 0.0188 (6) | −0.0057 (6) |
C1 | 0.0543 (10) | 0.0532 (10) | 0.0452 (10) | −0.0051 (8) | 0.0277 (8) | −0.0083 (8) |
C2 | 0.0391 (8) | 0.0383 (8) | 0.0380 (8) | −0.0006 (6) | 0.0175 (7) | −0.0014 (6) |
C3 | 0.0375 (8) | 0.0377 (8) | 0.0421 (9) | −0.0022 (6) | 0.0166 (7) | 0.0009 (7) |
C4 | 0.0532 (11) | 0.0568 (11) | 0.0551 (11) | −0.0033 (9) | 0.0341 (9) | −0.0013 (9) |
C5 | 0.0451 (9) | 0.0477 (10) | 0.0426 (9) | −0.0014 (8) | 0.0232 (8) | −0.0040 (7) |
C6 | 0.0339 (8) | 0.0364 (8) | 0.0380 (8) | 0.0000 (6) | 0.0173 (6) | 0.0009 (6) |
C7 | 0.0373 (8) | 0.0353 (8) | 0.0366 (8) | 0.0010 (6) | 0.0165 (6) | 0.0008 (6) |
C8 | 0.0372 (8) | 0.0430 (9) | 0.0459 (9) | −0.0035 (7) | 0.0164 (7) | 0.0020 (7) |
C9 | 0.0523 (12) | 0.0687 (14) | 0.0832 (16) | −0.0220 (10) | 0.0294 (12) | −0.0131 (12) |
C10 | 0.0479 (10) | 0.0613 (12) | 0.0577 (11) | −0.0047 (9) | 0.0307 (9) | −0.0026 (9) |
O2 | 0.0678 (9) | 0.0382 (7) | 0.0501 (8) | 0.0060 (6) | 0.0222 (7) | 0.0017 (6) |
Geometric parameters (Å, º) top
S1—C3 | 1.7262 (19) | C4—C5 | 1.335 (3) |
S1—C4 | 1.732 (2) | C6—C7 | 1.467 (2) |
O1—C7 | 1.222 (2) | C8—C10 | 1.493 (3) |
O2—H2A | 0.91 (3) | C8—C9 | 1.493 (3) |
O2—H2B | 0.83 (4) | C1—H1A | 0.9600 |
N1—C2 | 1.378 (2) | C1—H1B | 0.9600 |
N1—C3 | 1.321 (2) | C1—H1C | 0.9600 |
N2—C5 | 1.395 (2) | C4—H4 | 0.98 (3) |
N2—C3 | 1.353 (2) | C5—H5 | 0.97 (2) |
N2—C6 | 1.392 (2) | C9—H9B | 0.9600 |
N3—C7 | 1.351 (3) | C9—H9C | 0.9600 |
N3—N4 | 1.396 (2) | C9—H9A | 0.9600 |
N4—C8 | 1.276 (3) | C10—H10C | 0.9600 |
N3—H3 | 0.83 (2) | C10—H10A | 0.9600 |
C1—C2 | 1.496 (3) | C10—H10B | 0.9600 |
C2—C6 | 1.377 (2) | | |
| | | |
S1···O2 | 3.4069 (18) | C1···H3 | 2.80 (2) |
S1···S1i | 3.3954 (7) | C2···H3 | 2.81 (2) |
S1···O1ii | 3.2480 (16) | C2···H2Ai | 2.91 (3) |
S1···H5ii | 2.82 (2) | C3···H9Bv | 3.0300 |
S1···H10Aiii | 3.1100 | C3···H2Ai | 3.06 (3) |
O1···N2 | 2.840 (2) | C4···H10Aiii | 2.9900 |
O1···N4 | 2.695 (2) | C6···H9Aix | 2.9500 |
O1···C5 | 3.034 (2) | C7···H9Aix | 3.0700 |
O1···C4iv | 3.141 (3) | C7···H5 | 3.02 (2) |
O1···S1iv | 3.2480 (16) | C7···H10Cv | 3.0500 |
O1···O2iv | 3.196 (2) | C10···H3 | 2.63 (2) |
O1···C10v | 3.400 (3) | H1A···N3 | 2.8000 |
O2···N4ii | 3.018 (2) | H1A···H3 | 2.5400 |
O2···N1i | 2.883 (2) | H1A···O1v | 2.8000 |
O2···C10iii | 3.335 (3) | H1B···N4xi | 2.9100 |
O2···N3iii | 2.890 (2) | H1C···O2vi | 2.8500 |
O2···O1ii | 3.196 (2) | H1C···N1vii | 2.8900 |
O2···S1 | 3.4069 (18) | H2A···C2i | 2.91 (3) |
O1···H5 | 2.53 (2) | H2A···C3i | 3.06 (3) |
O1···H10Cv | 2.5400 | H2A···N1i | 1.98 (3) |
O1···H2Biv | 2.64 (3) | H2B···N4ii | 2.21 (4) |
O1···H1Av | 2.8000 | H2B···O1ii | 2.64 (3) |
O1···H4iv | 2.63 (2) | H3···C1 | 2.80 (2) |
O2···H3iii | 2.12 (2) | H3···O2vi | 2.12 (2) |
O2···H1Ciii | 2.8500 | H3···C10 | 2.63 (2) |
O2···H10Aiii | 2.6000 | H3···H1A | 2.5400 |
N1···N2 | 2.226 (2) | H3···C2 | 2.81 (2) |
N1···O2i | 2.883 (2) | H3···H10C | 2.4600 |
N2···O1 | 2.840 (2) | H3···H10A | 2.5400 |
N3···C1 | 3.204 (2) | H4···O1ii | 2.63 (2) |
N3···O2vi | 2.890 (2) | H5···S1iv | 2.82 (2) |
N4···O1 | 2.695 (2) | H5···C7 | 3.02 (2) |
N4···O2iv | 3.018 (2) | H5···O1 | 2.53 (2) |
N1···H1Cvii | 2.8900 | H9A···C6x | 2.9500 |
N1···H2Ai | 1.98 (3) | H9A···C7x | 3.0700 |
N3···H10A | 2.9200 | H9B···H10B | 2.4700 |
N3···H10C | 2.5700 | H9B···C3v | 3.0300 |
N3···H1A | 2.8000 | H10A···N3 | 2.9200 |
N4···H2Biv | 2.21 (4) | H10A···S1vi | 3.1100 |
N4···H1Bviii | 2.9100 | H10A···O2vi | 2.6000 |
C1···N3 | 3.204 (2) | H10A···C4vi | 2.9900 |
C4···O1ii | 3.141 (3) | H10A···H3 | 2.5400 |
C5···O1 | 3.034 (2) | H10B···H9B | 2.4700 |
C5···C9ix | 3.570 (3) | H10B···H10Bxii | 2.2200 |
C6···C8v | 3.550 (2) | H10C···C7v | 3.0500 |
C8···C6v | 3.550 (2) | H10C···N3 | 2.5700 |
C9···C5x | 3.570 (3) | H10C···H3 | 2.4600 |
C10···O1v | 3.400 (3) | H10C···O1v | 2.5400 |
C10···O2vi | 3.335 (3) | | |
| | | |
C3—S1—C4 | 89.49 (9) | N4—C8—C10 | 125.96 (17) |
H2A—O2—H2B | 98 (3) | C9—C8—C10 | 117.57 (17) |
C2—N1—C3 | 104.57 (14) | C2—C1—H1B | 109.00 |
C3—N2—C6 | 106.96 (14) | C2—C1—H1C | 110.00 |
C5—N2—C6 | 138.64 (15) | H1A—C1—H1B | 109.00 |
C3—N2—C5 | 114.32 (15) | H1A—C1—H1C | 109.00 |
N4—N3—C7 | 117.67 (14) | H1B—C1—H1C | 109.00 |
N3—N4—C8 | 115.75 (15) | C2—C1—H1A | 109.00 |
C7—N3—H3 | 115.1 (15) | S1—C4—H4 | 117.2 (14) |
N4—N3—H3 | 120.0 (15) | C5—C4—H4 | 129.1 (14) |
N1—C2—C1 | 119.71 (15) | C4—C5—H5 | 130.4 (13) |
N1—C2—C6 | 111.08 (16) | N2—C5—H5 | 118.4 (13) |
C1—C2—C6 | 129.14 (17) | C8—C9—H9A | 109.00 |
S1—C3—N2 | 111.31 (13) | C8—C9—H9B | 109.00 |
N1—C3—N2 | 112.70 (16) | H9A—C9—H9B | 109.00 |
S1—C3—N1 | 135.99 (14) | H9A—C9—H9C | 110.00 |
S1—C4—C5 | 113.69 (16) | C8—C9—H9C | 109.00 |
N2—C5—C4 | 111.18 (17) | H9B—C9—H9C | 109.00 |
N2—C6—C7 | 120.07 (14) | C8—C10—H10B | 109.00 |
C2—C6—C7 | 135.21 (17) | C8—C10—H10C | 109.00 |
N2—C6—C2 | 104.66 (15) | C8—C10—H10A | 109.00 |
N3—C7—C6 | 114.54 (15) | H10A—C10—H10C | 109.00 |
O1—C7—C6 | 121.35 (17) | H10B—C10—H10C | 110.00 |
O1—C7—N3 | 124.09 (16) | H10A—C10—H10B | 109.00 |
N4—C8—C9 | 116.47 (16) | | |
| | | |
C3—S1—C4—C5 | 0.57 (17) | C3—N2—C5—C4 | −0.4 (2) |
C4—S1—C3—N2 | −0.75 (14) | N4—N3—C7—C6 | −177.24 (14) |
C4—S1—C3—N1 | 178.8 (2) | C7—N3—N4—C8 | −165.58 (16) |
C2—N1—C3—N2 | 0.59 (19) | N4—N3—C7—O1 | 4.2 (3) |
C3—N1—C2—C1 | −176.61 (16) | N3—N4—C8—C10 | 3.1 (3) |
C3—N1—C2—C6 | 0.56 (19) | N3—N4—C8—C9 | −177.69 (16) |
C2—N1—C3—S1 | −178.93 (16) | N1—C2—C6—C7 | −178.57 (18) |
C5—N2—C6—C2 | 178.1 (2) | C1—C2—C6—C7 | −1.8 (3) |
C3—N2—C6—C7 | 179.39 (15) | N1—C2—C6—N2 | −1.42 (19) |
C3—N2—C6—C2 | 1.70 (18) | C1—C2—C6—N2 | 175.41 (17) |
C5—N2—C3—S1 | 0.79 (19) | S1—C4—C5—N2 | −0.2 (2) |
C6—N2—C3—S1 | 178.15 (11) | C2—C6—C7—N3 | −24.5 (3) |
C6—N2—C5—C4 | −176.55 (19) | C2—C6—C7—O1 | 154.1 (2) |
C6—N2—C3—N1 | −1.5 (2) | N2—C6—C7—N3 | 158.71 (15) |
C5—N2—C6—C7 | −4.3 (3) | N2—C6—C7—O1 | −22.7 (2) |
C5—N2—C3—N1 | −178.85 (15) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+2, −y+1, −z; (vi) x+1, y, z; (vii) −x+2, −y, −z; (viii) x+1/2, −y+1/2, z+1/2; (ix) −x+5/2, y−1/2, −z+1/2; (x) −x+5/2, y+1/2, −z+1/2; (xi) x−1/2, −y+1/2, z−1/2; (xii) −x+3, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N1i | 0.91 (3) | 1.98 (3) | 2.883 (2) | 172 (3) |
O2—H2B···N4ii | 0.83 (4) | 2.21 (4) | 3.018 (2) | 166 (3) |
N3—H3···O2vi | 0.83 (2) | 2.12 (2) | 2.890 (2) | 155 (2) |
C5—H5···O1 | 0.97 (2) | 2.53 (2) | 3.034 (2) | 112.2 (15) |
C5—H5···S1iv | 0.97 (2) | 2.82 (2) | 3.782 (2) | 172.0 (17) |
C10—H10C···O1v | 0.96 | 2.54 | 3.400 (3) | 149 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+2, −y+1, −z; (vi) x+1, y, z. |