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.
Supporting information
CCDC reference: 170294
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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-1
H-pyrazol-5-one dihydrate
top
Crystal data top
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) Å3 | Prisme, rouge |
Z = 4 | 0.50 × 0.40 × 0.30 mm |
F(000) = 752 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom, diff |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.068 | Weighting scheme based on measured s.u.'s w = 1 /[σ2(Fo2) + 0.03Fo2] |
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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |