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Acta Cryst. (2005). E61, o718-o720
https://doi.org/10.1107/S160053680500509X
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6-Methyl-N'-(1-methyl­ethyl­idene)­imidazo­[2,1-b][1,3]­thia­zole-5-carbohydrazide monohydrate

M. Akkurt, S. Ö. Yildirim, F. Ur, Z. Cesur, N. Cesur and O. Büyükgüngör
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.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500509X/fl6148sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500509X/fl6148Isup2.hkl
Contains datablock I

CCDC reference: 269560

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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
Computing details top

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·H2OF(000) = 536
Mr = 254.32Dx = 1.362 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 15184 reflections
a = 10.0955 (7) Åθ = 2.2–27.3°
b = 9.8500 (6) ŵ = 0.26 mm−1
c = 13.3756 (8) ÅT = 293 K
β = 111.226 (5)°Plate, pale yellow
V = 1239.85 (14) Å30.38 × 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 focus2217 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.054
Detector resolution: 6.67 pixels mm-1θmax = 27.3°, θmin = 2.2°
ω scansh = −12→12
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)		k = −12→12
Tmin = 0.908, Tmax = 0.980l = −17→17
15514 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) = 0.107H 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 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −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
xyzUiso*/Ueq
S10.59015 (5)0.08917 (5)0.11281 (4)0.0509 (2)
O10.96493 (14)0.48573 (13)0.17495 (12)0.0507 (4)
N10.76703 (16)0.10191 (15)−0.00967 (12)0.0427 (4)
N20.79432 (14)0.24803 (14)0.12330 (11)0.0351 (4)
N31.11971 (16)0.38670 (15)0.10899 (12)0.0391 (4)
N41.22016 (15)0.48839 (14)0.15339 (12)0.0411 (4)
C10.9522 (2)0.1793 (2)−0.07879 (15)0.0482 (6)
C20.87804 (18)0.18860 (16)−0.00035 (13)0.0375 (5)
C30.72089 (18)0.14103 (17)0.06647 (13)0.0385 (5)
C40.6426 (2)0.2149 (2)0.20978 (17)0.0510 (6)
C50.75030 (19)0.29057 (19)0.20577 (15)0.0431 (5)
C60.89932 (17)0.27927 (16)0.08240 (13)0.0349 (5)
C70.99670 (17)0.39293 (16)0.12722 (13)0.0355 (5)
C81.32008 (18)0.49642 (17)0.11652 (14)0.0417 (5)
C91.4316 (2)0.6011 (2)0.1661 (2)0.0667 (8)
C101.3341 (2)0.4123 (2)0.02807 (17)0.0524 (6)
O20.27396 (16)0.13305 (14)0.14617 (13)0.0518 (5)
H1A0.981000.26840−0.091900.0720*
H1B0.888800.14140−0.144900.0720*
H1C1.034400.12230−0.050000.0720*
H31.146 (2)0.309 (2)0.1008 (19)0.056 (6)*
H40.589 (3)0.223 (2)0.258 (2)0.071 (7)*
H50.800 (2)0.366 (2)0.2505 (17)0.046 (5)*
H9A1.408400.650700.219300.1000*
H9B1.436100.662500.111600.1000*
H9C1.522000.557400.199100.1000*
H10A1.368700.323700.055000.0790*
H10B1.399600.455000.000900.0790*
H10C1.243000.40400−0.028500.0790*
H2A0.268 (3)0.055 (3)0.108 (2)0.074 (7)*
H2B0.291 (3)0.098 (3)0.206 (3)0.086 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0482 (3)0.0513 (3)0.0616 (3)−0.0116 (2)0.0300 (2)−0.0020 (2)
O10.0501 (7)0.0455 (7)0.0661 (8)−0.0052 (6)0.0327 (7)−0.0171 (6)
N10.0454 (8)0.0413 (7)0.0445 (8)−0.0056 (6)0.0200 (7)−0.0058 (6)
N20.0352 (7)0.0366 (7)0.0376 (7)0.0007 (5)0.0180 (6)0.0003 (5)
N30.0382 (7)0.0366 (7)0.0479 (8)−0.0051 (6)0.0220 (6)−0.0071 (6)
N40.0405 (7)0.0389 (7)0.0464 (8)−0.0076 (6)0.0188 (6)−0.0057 (6)
C10.0543 (10)0.0532 (10)0.0452 (10)−0.0051 (8)0.0277 (8)−0.0083 (8)
C20.0391 (8)0.0383 (8)0.0380 (8)−0.0006 (6)0.0175 (7)−0.0014 (6)
C30.0375 (8)0.0377 (8)0.0421 (9)−0.0022 (6)0.0166 (7)0.0009 (7)
C40.0532 (11)0.0568 (11)0.0551 (11)−0.0033 (9)0.0341 (9)−0.0013 (9)
C50.0451 (9)0.0477 (10)0.0426 (9)−0.0014 (8)0.0232 (8)−0.0040 (7)
C60.0339 (8)0.0364 (8)0.0380 (8)0.0000 (6)0.0173 (6)0.0009 (6)
C70.0373 (8)0.0353 (8)0.0366 (8)0.0010 (6)0.0165 (6)0.0008 (6)
C80.0372 (8)0.0430 (9)0.0459 (9)−0.0035 (7)0.0164 (7)0.0020 (7)
C90.0523 (12)0.0687 (14)0.0832 (16)−0.0220 (10)0.0294 (12)−0.0131 (12)
C100.0479 (10)0.0613 (12)0.0577 (11)−0.0047 (9)0.0307 (9)−0.0026 (9)
O20.0678 (9)0.0382 (7)0.0501 (8)0.0060 (6)0.0222 (7)0.0017 (6)
Geometric parameters (Å, º) top
S1—C31.7262 (19)C4—C51.335 (3)
S1—C41.732 (2)C6—C71.467 (2)
O1—C71.222 (2)C8—C101.493 (3)
O2—H2A0.91 (3)C8—C91.493 (3)
O2—H2B0.83 (4)C1—H1A0.9600
N1—C21.378 (2)C1—H1B0.9600
N1—C31.321 (2)C1—H1C0.9600
N2—C51.395 (2)C4—H40.98 (3)
N2—C31.353 (2)C5—H50.97 (2)
N2—C61.392 (2)C9—H9B0.9600
N3—C71.351 (3)C9—H9C0.9600
N3—N41.396 (2)C9—H9A0.9600
N4—C81.276 (3)C10—H10C0.9600
N3—H30.83 (2)C10—H10A0.9600
C1—C21.496 (3)C10—H10B0.9600
C2—C61.377 (2)
S1···O23.4069 (18)C1···H32.80 (2)
S1···S1i3.3954 (7)C2···H32.81 (2)
S1···O1ii3.2480 (16)C2···H2Ai2.91 (3)
S1···H5ii2.82 (2)C3···H9Bv3.0300
S1···H10Aiii3.1100C3···H2Ai3.06 (3)
O1···N22.840 (2)C4···H10Aiii2.9900
O1···N42.695 (2)C6···H9Aix2.9500
O1···C53.034 (2)C7···H9Aix3.0700
O1···C4iv3.141 (3)C7···H53.02 (2)
O1···S1iv3.2480 (16)C7···H10Cv3.0500
O1···O2iv3.196 (2)C10···H32.63 (2)
O1···C10v3.400 (3)H1A···N32.8000
O2···N4ii3.018 (2)H1A···H32.5400
O2···N1i2.883 (2)H1A···O1v2.8000
O2···C10iii3.335 (3)H1B···N4xi2.9100
O2···N3iii2.890 (2)H1C···O2vi2.8500
O2···O1ii3.196 (2)H1C···N1vii2.8900
O2···S13.4069 (18)H2A···C2i2.91 (3)
O1···H52.53 (2)H2A···C3i3.06 (3)
O1···H10Cv2.5400H2A···N1i1.98 (3)
O1···H2Biv2.64 (3)H2B···N4ii2.21 (4)
O1···H1Av2.8000H2B···O1ii2.64 (3)
O1···H4iv2.63 (2)H3···C12.80 (2)
O2···H3iii2.12 (2)H3···O2vi2.12 (2)
O2···H1Ciii2.8500H3···C102.63 (2)
O2···H10Aiii2.6000H3···H1A2.5400
N1···N22.226 (2)H3···C22.81 (2)
N1···O2i2.883 (2)H3···H10C2.4600
N2···O12.840 (2)H3···H10A2.5400
N3···C13.204 (2)H4···O1ii2.63 (2)
N3···O2vi2.890 (2)H5···S1iv2.82 (2)
N4···O12.695 (2)H5···C73.02 (2)
N4···O2iv3.018 (2)H5···O12.53 (2)
N1···H1Cvii2.8900H9A···C6x2.9500
N1···H2Ai1.98 (3)H9A···C7x3.0700
N3···H10A2.9200H9B···H10B2.4700
N3···H10C2.5700H9B···C3v3.0300
N3···H1A2.8000H10A···N32.9200
N4···H2Biv2.21 (4)H10A···S1vi3.1100
N4···H1Bviii2.9100H10A···O2vi2.6000
C1···N33.204 (2)H10A···C4vi2.9900
C4···O1ii3.141 (3)H10A···H32.5400
C5···O13.034 (2)H10B···H9B2.4700
C5···C9ix3.570 (3)H10B···H10Bxii2.2200
C6···C8v3.550 (2)H10C···C7v3.0500
C8···C6v3.550 (2)H10C···N32.5700
C9···C5x3.570 (3)H10C···H32.4600
C10···O1v3.400 (3)H10C···O1v2.5400
C10···O2vi3.335 (3)
C3—S1—C489.49 (9)N4—C8—C10125.96 (17)
H2A—O2—H2B98 (3)C9—C8—C10117.57 (17)
C2—N1—C3104.57 (14)C2—C1—H1B109.00
C3—N2—C6106.96 (14)C2—C1—H1C110.00
C5—N2—C6138.64 (15)H1A—C1—H1B109.00
C3—N2—C5114.32 (15)H1A—C1—H1C109.00
N4—N3—C7117.67 (14)H1B—C1—H1C109.00
N3—N4—C8115.75 (15)C2—C1—H1A109.00
C7—N3—H3115.1 (15)S1—C4—H4117.2 (14)
N4—N3—H3120.0 (15)C5—C4—H4129.1 (14)
N1—C2—C1119.71 (15)C4—C5—H5130.4 (13)
N1—C2—C6111.08 (16)N2—C5—H5118.4 (13)
C1—C2—C6129.14 (17)C8—C9—H9A109.00
S1—C3—N2111.31 (13)C8—C9—H9B109.00
N1—C3—N2112.70 (16)H9A—C9—H9B109.00
S1—C3—N1135.99 (14)H9A—C9—H9C110.00
S1—C4—C5113.69 (16)C8—C9—H9C109.00
N2—C5—C4111.18 (17)H9B—C9—H9C109.00
N2—C6—C7120.07 (14)C8—C10—H10B109.00
C2—C6—C7135.21 (17)C8—C10—H10C109.00
N2—C6—C2104.66 (15)C8—C10—H10A109.00
N3—C7—C6114.54 (15)H10A—C10—H10C109.00
O1—C7—C6121.35 (17)H10B—C10—H10C110.00
O1—C7—N3124.09 (16)H10A—C10—H10B109.00
N4—C8—C9116.47 (16)
C3—S1—C4—C50.57 (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—N1178.8 (2)C7—N3—N4—C8−165.58 (16)
C2—N1—C3—N20.59 (19)N4—N3—C7—O14.2 (3)
C3—N1—C2—C1−176.61 (16)N3—N4—C8—C103.1 (3)
C3—N1—C2—C60.56 (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—C2178.1 (2)C1—C2—C6—C7−1.8 (3)
C3—N2—C6—C7179.39 (15)N1—C2—C6—N2−1.42 (19)
C3—N2—C6—C21.70 (18)C1—C2—C6—N2175.41 (17)
C5—N2—C3—S10.79 (19)S1—C4—C5—N2−0.2 (2)
C6—N2—C3—S1178.15 (11)C2—C6—C7—N3−24.5 (3)
C6—N2—C5—C4−176.55 (19)C2—C6—C7—O1154.1 (2)
C6—N2—C3—N1−1.5 (2)N2—C6—C7—N3158.71 (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···AD—HH···AD···AD—H···A
O2—H2A···N1i0.91 (3)1.98 (3)2.883 (2)172 (3)
O2—H2B···N4ii0.83 (4)2.21 (4)3.018 (2)166 (3)
N3—H3···O2vi0.83 (2)2.12 (2)2.890 (2)155 (2)
C5—H5···O10.97 (2)2.53 (2)3.034 (2)112.2 (15)
C5—H5···S1iv0.97 (2)2.82 (2)3.782 (2)172.0 (17)
C10—H10C···O1v0.962.543.400 (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.
 

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