3-Methyl-4-(7-methylthiazolo[3,2-a]pyrimidin-5-yl)-2-phenyl-1H-pyrazol-5-one dihydrate

The structure of the title compound, C₁₇H₁₄N₄OS·2H₂O, has been established by an X-ray crystallographic study. It crystallizes with two water molecules which are involved in two intramolecular and one intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.048
• wR factor = 0.068
• Data-to-parameter ratio = 8.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          rouge

CRYSC_01  Alert C No recognised colour has been given for crystal colour.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.38
         From the CIF: _reflns_number_total               1759
         Count of symmetry unique reflns         1793
         Completeness (_total/calc)             98.10%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus (Mackay et al., 1999); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: maXus.

3-Methyl-4-(7-methylthiazolo[3,2-a]pyrimidin-5-yl)-2-phenyl-1H-pyrazol-5-one dihydrate

Crystal data

C17H14N4OS·2H2O	Dx = 1.403 Mg m^−3
Mr = 358.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 11.974 reflections
a = 10.0535 (2) Å	θ = 1–25.3°
b = 10.9029 (3) Å	µ = 0.22 mm^−1
c = 15.4808 (5) Å	T = 298 K
V = 1696.89 (8) Å^3	Prisme, rouge
Z = 4	0.50 × 0.40 × 0.30 mm
F(000) = 752

Data collection

KappaCCD diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 25.4°
φ scan	h = 0→11
1851 measured reflections	k = 0→13
1759 independent reflections	l = 0→19
1726 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom, diff
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.068	Weighting scheme based on measured s.u.'s w = 1 /[σ^2(Fo^2) + 0.03Fo^2]
S = 1.86	(Δ/σ)max = 0.008
1726 reflections	Δρmax = 0.41 e Å^−3
213 parameters	Δρmin = −0.81 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.29350 (2)	0.524390 (18)	0.207952 (13)	0.03785 (5)*
O17	0.1861 (17)	0.7045 (14)	0.1803 (11)	0.0366 (3)
O24	0.36576 (7)	0.74276 (7)	0.31752 (4)	0.0600 (4)
O25	0.26024 (9)	0.77902 (6)	0.48815 (5)	0.0757 (5)
N3	−0.13838 (6)	0.70939 (5)	0.19417 (4)	0.0267 (3)
N6	−0.32606 (6)	0.74093 (6)	0.28683 (4)	0.0340 (3)
N11	0.16487 (6)	1.00027 (5)	0.09123 (4)	0.0308 (3)
N12	0.22914 (7)	0.88971 (7)	0.10855 (5)	0.0286 (3)
C2	−0.25302 (8)	0.67288 (7)	0.23491 (5)	0.0297 (3)
C4	−0.08615 (9)	0.61977 (7)	0.13880 (5)	0.0346 (4)
C5	−0.15852 (9)	0.51627 (7)	0.13991 (5)	0.0386 (4)
C7	−0.28203 (8)	0.85484 (7)	0.29990 (5)	0.0351 (4)
C8	−0.16830 (8)	0.90095 (7)	0.25935 (5)	0.0337 (4)
C9	−0.09181 (7)	0.82945 (6)	0.20527 (5)	0.0280 (4)
C10	−0.35667 (11)	0.93188 (8)	0.36299 (6)	0.0519 (5)
C13	0.14839 (8)	0.80716 (6)	0.15224 (5)	0.0286 (4)
C14	0.02441 (8)	0.86994 (6)	0.16126 (5)	0.0287 (4)
C15	0.04552 (8)	0.98855 (7)	0.12474 (5)	0.0305 (4)
C16	−0.05120 (9)	1.09263 (7)	0.11622 (6)	0.0414 (4)
C18	0.36713 (8)	0.87873 (6)	0.08993 (5)	0.0275 (4)
C19	0.44390 (8)	0.98406 (8)	0.08217 (5)	0.0387 (4)
C20	0.57781 (9)	0.97353 (9)	0.06292 (6)	0.0464 (5)
C21	0.63724 (9)	0.85982 (9)	0.05180 (5)	0.0443 (5)
C22	0.56009 (9)	0.75577 (9)	0.05942 (5)	0.0417 (5)
C23	0.42648 (9)	0.76447 (7)	0.07916 (5)	0.0342 (4)
H4	−0.0090	0.6253	0.1024	0.054561*
H5	−0.1328	0.4476	0.1049	0.058620*
H8	−0.1422	0.9851	0.2680	0.053746*
H19	0.4041	1.0638	0.0889	0.058702*
H20	0.6310	1.0463	0.0572	0.066406*
H21	0.7304	0.8528	0.0394	0.064324*
H22	0.5986	0.6761	0.0508	0.061689*
H23	0.3743	0.6914	0.0861	0.054236*
H10A	−0.3172	1.0116	0.3673	0.071882*
H10B	−0.3542	0.8927	0.4185	0.071882*
H10C	−0.4474	0.9400	0.3445	0.071882*
H16A	−0.0077	1.1604	0.0886	0.061369*
H16B	−0.0810	1.1171	0.1726	0.061369*
H16C	−0.1262	1.0675	0.0822	0.0614*
H24A	0.4704	0.7399	0.3079	0.080*
H24B	0.3205	0.7047	0.2732	0.080*
H25A	0.3192	0.7738	0.4363	0.0957*
H25B	0.2685	0.8594	0.5217	0.0957*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O17	0.0370	0.0275 (3)	0.0454 (3)	0.0015 (2)	0.0009 (2)	0.0066 (2)
O24	0.0519 (4)	0.0760 (5)	0.0522 (4)	−0.0044 (4)	−0.0044 (3)	0.0008 (4)
O25	0.0975 (7)	0.0544 (4)	0.0754 (5)	−0.0244 (4)	0.0125 (4)	−0.0210 (4)
N3	0.0267 (3)	0.0233 (3)	0.0302 (3)	−0.0042 (3)	0.0001 (3)	0.0002 (2)
N6	0.0306 (4)	0.0311 (3)	0.0404 (3)	−0.0037 (3)	0.0047 (3)	0.0011 (3)
N11	0.0267 (4)	0.0256 (3)	0.0402 (3)	−0.0023 (2)	−0.0011 (3)	0.0058 (3)
N12	0.0244 (4)	0.0252 (3)	0.0362 (3)	0.0012 (3)	0.0032 (3)	0.0035 (3)
C2	0.0282 (4)	0.0276 (4)	0.0332 (4)	−0.0032 (3)	−0.0032 (3)	0.0043 (3)
C4	0.0418 (5)	0.0285 (4)	0.0333 (4)	0.0002 (3)	0.0042 (3)	−0.0036 (3)
C5	0.0476 (5)	0.0283 (4)	0.0400 (4)	−0.0028 (4)	−0.0037 (3)	−0.0051 (3)
C7	0.0331 (4)	0.0308 (4)	0.0414 (4)	0.0041 (4)	−0.0009 (4)	0.0005 (3)
C8	0.0373 (5)	0.0226 (4)	0.0413 (4)	−0.0032 (3)	0.0013 (3)	−0.0016 (3)
C9	0.0302 (4)	0.0211 (3)	0.0328 (4)	−0.0038 (3)	−0.0036 (3)	0.0035 (3)
C10	0.0460 (6)	0.0427 (5)	0.0669 (6)	0.0021 (4)	0.0155 (5)	−0.0072 (4)
C13	0.0335 (4)	0.0224 (4)	0.0297 (4)	−0.0030 (3)	−0.0006 (3)	−0.0018 (3)
C14	0.0293 (4)	0.0230 (4)	0.0339 (4)	−0.0027 (3)	0.0012 (3)	−0.0018 (3)
C15	0.0307 (4)	0.0258 (4)	0.0350 (4)	−0.0047 (3)	−0.0022 (3)	0.0000 (3)
C16	0.0381 (5)	0.0313 (4)	0.0547 (5)	0.0063 (4)	−0.0035 (4)	0.0058 (4)
C18	0.0262 (4)	0.0266 (4)	0.0297 (4)	−0.0046 (3)	0.0017 (3)	−0.0012 (3)
C19	0.0344 (5)	0.0325 (4)	0.0492 (5)	−0.0032 (4)	0.0044 (4)	−0.0086 (4)
C20	0.0345 (5)	0.0488 (5)	0.0559 (5)	−0.0134 (4)	0.0046 (4)	−0.0095 (5)
C21	0.0296 (5)	0.0610 (6)	0.0424 (5)	0.0030 (4)	0.0014 (4)	−0.0043 (4)
C22	0.0406 (5)	0.0490 (5)	0.0354 (4)	0.0124 (4)	0.0031 (4)	0.0023 (4)
C23	0.0385 (5)	0.0295 (4)	0.0347 (4)	0.0052 (3)	0.0034 (3)	0.0052 (3)

Geometric parameters (Å, º)

S1—C2	1.7207 (7)	C7—C8	1.3980 (11)
S1—C5	1.7202 (9)	C7—C10	1.4908 (11)
O17—C13	1.259 (16)	C8—C9	1.3785 (11)
N3—C2	1.3727 (9)	C9—C14	1.4229 (10)
N3—C4	1.4019 (9)	C13—C14	1.4289 (10)
N3—C9	1.4008 (9)	C14—C15	1.4272 (10)
N6—C2	1.3176 (10)	C15—C16	1.5002 (11)
N6—C7	1.3339 (10)	C18—C19	1.3890 (11)
N11—N12	1.3937 (5)	C18—C23	1.3913 (11)
N11—C15	1.3135 (9)	C19—C20	1.3836 (12)
N12—C13	1.3881 (7)	C20—C21	1.3870 (13)
N12—C18	1.4220 (8)	C21—C22	1.3794 (13)
C4—C5	1.3429 (11)	C22—C23	1.3809 (12)
C2—S1—C5	90.59 (4)	N3—C9—C14	120.38 (7)
C2—N3—C4	113.16 (6)	C8—C9—C14	124.99 (7)
C2—N3—C9	119.69 (6)	O17—C13—N12	124.6 (8)
C4—N3—C9	126.94 (7)	O17—C13—C14	130.9 (8)
C2—N6—C7	115.59 (7)	N12—C13—C14	104.31 (5)
N12—N11—C15	105.27 (5)	C9—C14—C13	127.91 (6)
N11—N12—C13	112.55 (4)	C9—C14—C15	126.37 (7)
N11—N12—C18	119.09 (4)	C13—C14—C15	105.41 (6)
C13—N12—C18	127.94 (4)	N11—C15—C14	112.36 (6)
S1—C2—N3	111.10 (5)	N11—C15—C16	118.94 (7)
S1—C2—N6	123.09 (6)	C14—C15—C16	128.59 (7)
N3—C2—N6	125.80 (7)	N12—C18—C19	119.35 (6)
N3—C4—C5	112.02 (7)	N12—C18—C23	121.21 (6)
S1—C5—C4	113.08 (6)	C19—C18—C23	119.45 (8)
N6—C7—C8	122.56 (7)	C18—C19—C20	119.39 (9)
N6—C7—C10	117.19 (7)	C19—C20—C21	121.34 (9)
C8—C7—C10	120.21 (7)	C20—C21—C22	118.84 (8)
C7—C8—C9	121.71 (7)	C21—C22—C23	120.63 (8)
N3—C9—C8	114.62 (7)	C18—C23—C22	120.35 (8)