3-(3-Hydroxy­propyl)-6-(p-tolyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]­thia­diazine dihydrate

In the title compound, C₁₄H₁₆N₄OS·2H₂O, the five-membered triazole ring makes a dihedral angle of 13.2 (2)° with the six-membered thia­diazole ring. This latter ring is almost planar, with a maximum deviation from the mean plane of 0.357 (2) Å for the methyl­ene C atom. The crystal packing is stabilized by intermolecular O—H...N and O—H...O hydrogen bonds involving the two solvent water mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.072
• wR factor = 0.157
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1     ..  H3B     ..       2.11 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

3-(3-Hydroxypropyl)-6-(4-methylphenyl)-7H-1,2,4-triazolo [3,4-b][1,3,4]thiadiazine dihydrate

Crystal data

C14H16N4OS·2H2O	F(000) = 688
Mr = 324.40	Dx = 1.326 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1273 reflections
a = 12.7018 (12) Å	θ = 3.0–21.6°
b = 7.3602 (7) Å	µ = 0.22 mm^−1
c = 17.3967 (17) Å	T = 298 K
β = 92.612 (2)°	Rod, colourless
V = 1624.7 (3) Å^3	0.48 × 0.16 × 0.15 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2921 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→15
Tmin = 0.903, Tmax = 0.958	k = −8→8
8314 measured reflections	l = −14→20

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.7142P] where P = (Fo^2 + 2Fc^2)/3
2921 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.27 e Å^−3
6 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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	0.75729 (8)	0.01928 (14)	0.42808 (5)	0.0612 (3)
O1	1.1519 (2)	0.0288 (3)	0.80555 (16)	0.0694 (8)
H1	1.2048	−0.0137	0.7870	0.104*
O2	0.0290 (2)	0.4303 (3)	0.62199 (14)	0.0682 (8)
O3	0.3352 (2)	0.8878 (4)	0.75313 (19)	0.0813 (9)
N1	0.80952 (19)	0.1861 (3)	0.59227 (14)	0.0420 (6)
N2	0.86106 (18)	0.0329 (3)	0.56629 (14)	0.0391 (6)
N3	0.9003 (2)	−0.2096 (4)	0.50056 (15)	0.0522 (7)
N4	0.9549 (2)	−0.2141 (4)	0.57239 (15)	0.0463 (7)
C1	0.5761 (3)	0.9549 (5)	0.6463 (3)	0.0800 (13)
H1A	0.5401	1.0151	0.6038	0.120*
H1B	0.6302	1.0331	0.6679	0.120*
H1C	0.5268	0.9268	0.6848	0.120*
C2	0.6258 (3)	0.7798 (5)	0.6183 (2)	0.0588 (10)
C3	0.5969 (3)	0.7070 (5)	0.5481 (2)	0.0642 (11)
H3	0.5457	0.7658	0.5173	0.077*
C4	0.6413 (3)	0.5491 (5)	0.5217 (2)	0.0563 (9)
H4	0.6197	0.5035	0.4737	0.068*
C5	0.7176 (2)	0.4580 (4)	0.56588 (19)	0.0434 (8)
C6	0.7479 (3)	0.5322 (5)	0.6368 (2)	0.0517 (9)
H6	0.7993	0.4742	0.6676	0.062*
C7	0.7033 (3)	0.6892 (5)	0.6621 (2)	0.0596 (10)
H7	0.7255	0.7363	0.7098	0.072*
C8	0.7684 (2)	0.2896 (4)	0.53914 (18)	0.0422 (8)
C9	0.7778 (3)	0.2549 (5)	0.45486 (19)	0.0536 (9)
H9A	0.8473	0.2920	0.4402	0.064*
H9B	0.7265	0.3293	0.4263	0.064*
C10	0.8447 (2)	−0.0617 (4)	0.49931 (18)	0.0424 (8)
C11	0.9306 (2)	−0.0698 (4)	0.61050 (17)	0.0384 (7)
C12	0.9717 (3)	−0.0149 (4)	0.68842 (18)	0.0510 (9)
H12A	0.9132	0.0233	0.7185	0.061*
H12B	1.0184	0.0884	0.6836	0.061*
C13	1.0306 (3)	−0.1652 (5)	0.73052 (19)	0.0524 (9)
H13A	0.9836	−0.2678	0.7361	0.063*
H13B	1.0884	−0.2048	0.7000	0.063*
C14	1.0737 (3)	−0.1081 (5)	0.8090 (2)	0.0617 (10)
H14A	1.0163	−0.0635	0.8387	0.074*
H14B	1.1037	−0.2133	0.8354	0.074*
H2A	0.007 (3)	0.532 (3)	0.6094 (19)	0.074*
H2B	0.047 (3)	0.368 (4)	0.5850 (16)	0.074*
H3A	0.335 (3)	0.780 (3)	0.7371 (18)	0.074*
H3B	0.363 (3)	0.897 (4)	0.7972 (13)	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0673 (6)	0.0676 (7)	0.0467 (6)	0.0036 (5)	−0.0195 (4)	0.0025 (5)
O1	0.0751 (18)	0.0611 (17)	0.0694 (19)	0.0044 (14)	−0.0243 (15)	−0.0094 (14)
O2	0.095 (2)	0.0467 (16)	0.0613 (17)	0.0139 (15)	−0.0094 (15)	0.0004 (13)
O3	0.080 (2)	0.073 (2)	0.088 (2)	0.0059 (17)	−0.0244 (17)	0.0008 (17)
N1	0.0401 (14)	0.0420 (15)	0.0435 (16)	0.0024 (12)	−0.0025 (12)	0.0051 (13)
N2	0.0412 (14)	0.0369 (15)	0.0386 (15)	0.0035 (12)	−0.0038 (12)	0.0038 (12)
N3	0.0612 (18)	0.0491 (18)	0.0454 (17)	0.0046 (15)	−0.0084 (14)	−0.0047 (14)
N4	0.0525 (16)	0.0407 (16)	0.0448 (16)	0.0040 (13)	−0.0066 (13)	0.0006 (13)
C1	0.073 (3)	0.056 (3)	0.113 (4)	0.014 (2)	0.025 (3)	−0.008 (2)
C2	0.052 (2)	0.048 (2)	0.078 (3)	−0.0004 (18)	0.019 (2)	0.007 (2)
C3	0.054 (2)	0.058 (2)	0.080 (3)	0.0163 (19)	0.000 (2)	0.016 (2)
C4	0.055 (2)	0.057 (2)	0.056 (2)	0.0086 (18)	−0.0070 (17)	0.0043 (18)
C5	0.0378 (17)	0.046 (2)	0.047 (2)	0.0014 (14)	0.0019 (15)	0.0113 (16)
C6	0.0474 (19)	0.053 (2)	0.054 (2)	0.0084 (16)	−0.0021 (17)	0.0071 (18)
C7	0.062 (2)	0.056 (2)	0.062 (2)	−0.0007 (19)	0.0068 (19)	−0.0031 (19)
C8	0.0326 (16)	0.047 (2)	0.0465 (19)	0.0000 (14)	−0.0014 (14)	0.0091 (16)
C9	0.054 (2)	0.061 (2)	0.047 (2)	0.0144 (17)	0.0080 (16)	0.0176 (17)
C10	0.0454 (18)	0.045 (2)	0.0364 (18)	−0.0041 (15)	−0.0041 (14)	0.0015 (15)
C11	0.0400 (17)	0.0357 (18)	0.0388 (18)	−0.0009 (14)	−0.0049 (14)	0.0055 (14)
C12	0.061 (2)	0.045 (2)	0.046 (2)	0.0108 (17)	−0.0106 (16)	−0.0015 (16)
C13	0.065 (2)	0.045 (2)	0.046 (2)	−0.0007 (17)	−0.0092 (17)	0.0099 (16)
C14	0.075 (3)	0.063 (2)	0.046 (2)	0.007 (2)	−0.0118 (19)	0.0037 (19)

Geometric parameters (Å, º)

S1—C10	1.732 (3)	C3—C4	1.380 (5)
S1—C9	1.811 (4)	C3—H3	0.9300
O1—C14	1.418 (4)	C4—C5	1.383 (4)
O1—H1	0.8200	C4—H4	0.9300
O2—H2A	0.826 (17)	C5—C6	1.387 (4)
O2—H2B	0.832 (17)	C5—C8	1.482 (4)
O3—H3A	0.838 (17)	C6—C7	1.369 (5)
O3—H3B	0.832 (17)	C6—H6	0.9300
N1—C8	1.290 (4)	C7—H7	0.9300
N1—N2	1.389 (3)	C8—C9	1.498 (5)
N2—C10	1.365 (4)	C9—H9A	0.9700
N2—C11	1.371 (3)	C9—H9B	0.9700
N3—C10	1.297 (4)	C11—C12	1.486 (4)
N3—N4	1.402 (4)	C12—C13	1.507 (4)
N4—C11	1.297 (4)	C12—H12A	0.9700
C1—C2	1.525 (5)	C12—H12B	0.9700
C1—H1A	0.9600	C13—C14	1.507 (4)
C1—H1B	0.9600	C13—H13A	0.9700
C1—H1C	0.9600	C13—H13B	0.9700
C2—C3	1.367 (5)	C14—H14A	0.9700
C2—C7	1.389 (5)	C14—H14B	0.9700
C10—S1—C9	93.76 (16)	N1—C8—C5	115.9 (3)
C14—O1—H1	109.5	N1—C8—C9	123.6 (3)
H2A—O2—H2B	114 (2)	C5—C8—C9	120.3 (3)
H3A—O3—H3B	112 (2)	C8—C9—S1	113.5 (2)
C8—N1—N2	115.3 (3)	C8—C9—H9A	108.9
C10—N2—C11	105.4 (3)	S1—C9—H9A	108.9
C10—N2—N1	129.5 (2)	C8—C9—H9B	108.9
C11—N2—N1	124.5 (2)	S1—C9—H9B	108.9
C10—N3—N4	106.4 (3)	H9A—C9—H9B	107.7
C11—N4—N3	108.4 (2)	N3—C10—N2	110.6 (3)
C2—C1—H1A	109.5	N3—C10—S1	129.2 (3)
C2—C1—H1B	109.5	N2—C10—S1	120.2 (2)
H1A—C1—H1B	109.5	N4—C11—N2	109.1 (3)
C2—C1—H1C	109.5	N4—C11—C12	127.4 (3)
H1A—C1—H1C	109.5	N2—C11—C12	123.5 (3)
H1B—C1—H1C	109.5	C11—C12—C13	112.9 (3)
C3—C2—C7	117.2 (3)	C11—C12—H12A	109.0
C3—C2—C1	121.2 (4)	C13—C12—H12A	109.0
C7—C2—C1	121.6 (4)	C11—C12—H12B	109.0
C2—C3—C4	122.0 (3)	C13—C12—H12B	109.0
C2—C3—H3	119.0	H12A—C12—H12B	107.8
C4—C3—H3	119.0	C14—C13—C12	112.8 (3)
C3—C4—C5	120.7 (4)	C14—C13—H13A	109.0
C3—C4—H4	119.7	C12—C13—H13A	109.0
C5—C4—H4	119.7	C14—C13—H13B	109.0
C4—C5—C6	117.5 (3)	C12—C13—H13B	109.0
C4—C5—C8	122.4 (3)	H13A—C13—H13B	107.8
C6—C5—C8	120.1 (3)	O1—C14—C13	112.7 (3)
C7—C6—C5	121.2 (3)	O1—C14—H14A	109.0
C7—C6—H6	119.4	C13—C14—H14A	109.0
C5—C6—H6	119.4	O1—C14—H14B	109.0
C6—C7—C2	121.4 (4)	C13—C14—H14B	109.0
C6—C7—H7	119.3	H14A—C14—H14B	107.8
C2—C7—H7	119.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2^i	0.83 (2)	1.93 (2)	2.730 (4)	160 (4)
O3—H3A···O1^ii	0.84 (2)	2.01 (2)	2.840 (4)	174 (4)
O2—H2B···N3^iii	0.83 (2)	2.03 (2)	2.858 (4)	176 (4)
O2—H2A···N4^iv	0.83 (2)	2.07 (2)	2.899 (4)	177 (3)
O1—H1···O3^v	0.82	1.93	2.743 (4)	175

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