3-[6-(4-Meth­oxyphen­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-3-yl]propan-1-ol

In the title compound, C₁₄H₁₆N₄O₂S, the six-membered thiadiazine ring adopts a distorted boat conformation. O—H...N hydrogen bonds link the mol­ecules into centrosymmetric dimers and enhance the stability of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.062
• wR factor = 0.137
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact  H6     ..  H9B     ..       1.93 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 5 Informative message, check

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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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

3-[6-(4-Methoxy-phenyl)-7H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazin-3-yl]-propan-1-ol

Crystal data

C14H16N4O2S	F(000) = 640
Mr = 304.38	Dx = 1.391 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1971 reflections
a = 7.6166 (7) Å	θ = 2.7–24.3°
b = 12.8582 (12) Å	µ = 0.23 mm^−1
c = 15.9198 (13) Å	T = 298 K
β = 111.228 (4)°	Block, colourless
V = 1453.3 (2) Å^3	0.25 × 0.17 × 0.16 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2556 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
Tmin = 0.944, Tmax = 0.959	k = −15→11
7493 measured reflections	l = −15→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.734P] where P = (Fo^2 + 2Fc^2)/3
2556 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.31 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	1.11651 (11)	0.94360 (6)	0.75106 (5)	0.0484 (3)
O1	0.4317 (3)	1.29997 (16)	0.34746 (14)	0.0615 (7)
O2	0.7299 (3)	0.53043 (15)	0.33859 (13)	0.0545 (6)
H2	0.7836	0.4740	0.3466	0.065*
N1	0.8681 (3)	0.89994 (15)	0.54673 (14)	0.0337 (5)
N2	0.9609 (3)	0.82075 (15)	0.60587 (14)	0.0339 (5)
N3	1.1541 (4)	0.73633 (18)	0.72224 (15)	0.0461 (6)
N4	1.0843 (4)	0.66829 (18)	0.64868 (16)	0.0477 (6)
C1	0.3593 (5)	1.2855 (3)	0.2525 (2)	0.0627 (10)
H1A	0.4610	1.2704	0.2323	0.094*
H1B	0.2962	1.3478	0.2237	0.094*
H1C	0.2717	1.2286	0.2373	0.094*
C2	0.5332 (4)	1.2211 (2)	0.39987 (19)	0.0418 (7)
C3	0.5565 (4)	1.1240 (2)	0.36866 (18)	0.0393 (7)
H3	0.5039	1.1090	0.3074	0.047*
C4	0.6580 (4)	1.0491 (2)	0.42867 (18)	0.0395 (7)
H4	0.6727	0.9838	0.4069	0.047*
C5	0.7391 (4)	1.06830 (19)	0.52069 (18)	0.0328 (6)
C6	0.7164 (4)	1.1669 (2)	0.55045 (19)	0.0475 (8)
H6	0.7696	1.1823	0.6116	0.057*
C7	0.6167 (5)	1.2422 (2)	0.4911 (2)	0.0553 (9)
H7	0.6051	1.3082	0.5125	0.066*
C8	0.8415 (3)	0.98471 (19)	0.58290 (17)	0.0316 (6)
C9	0.8928 (4)	1.0002 (2)	0.68300 (18)	0.0434 (7)
H9A	0.7948	0.9700	0.7007	0.052*
H9B	0.8965	1.0742	0.6954	0.052*
C10	1.0780 (4)	0.8261 (2)	0.69417 (17)	0.0357 (6)
C11	0.9708 (4)	0.7201 (2)	0.58061 (17)	0.0381 (6)
C12	0.8598 (5)	0.6788 (2)	0.48922 (19)	0.0462 (8)
H12A	0.9427	0.6699	0.4557	0.055*
H12B	0.7641	0.7292	0.4573	0.055*
C13	0.7654 (4)	0.5756 (2)	0.49244 (19)	0.0409 (7)
H13A	0.8612	0.5229	0.5178	0.049*
H13B	0.6935	0.5821	0.5315	0.049*
C14	0.6358 (4)	0.5415 (2)	0.3997 (2)	0.0507 (8)
H14A	0.5784	0.4756	0.4047	0.061*
H14B	0.5357	0.5923	0.3761	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0535 (5)	0.0455 (5)	0.0338 (4)	−0.0003 (3)	0.0010 (3)	−0.0080 (3)
O1	0.0816 (16)	0.0413 (12)	0.0495 (13)	0.0248 (11)	0.0094 (12)	0.0031 (10)
O2	0.0859 (16)	0.0385 (11)	0.0416 (12)	0.0138 (11)	0.0262 (12)	0.0022 (9)
N1	0.0420 (13)	0.0260 (11)	0.0304 (11)	0.0031 (9)	0.0100 (10)	0.0023 (9)
N2	0.0433 (13)	0.0283 (12)	0.0273 (11)	0.0001 (9)	0.0093 (10)	0.0020 (9)
N3	0.0568 (16)	0.0428 (14)	0.0321 (13)	0.0052 (12)	0.0082 (11)	0.0051 (11)
N4	0.0646 (17)	0.0363 (13)	0.0357 (13)	0.0074 (12)	0.0104 (12)	0.0036 (11)
C1	0.077 (2)	0.0504 (19)	0.0457 (19)	0.0195 (17)	0.0048 (17)	0.0105 (15)
C2	0.0443 (16)	0.0353 (15)	0.0442 (16)	0.0084 (12)	0.0140 (13)	0.0037 (13)
C3	0.0472 (16)	0.0369 (15)	0.0307 (14)	0.0006 (12)	0.0103 (12)	−0.0021 (12)
C4	0.0535 (18)	0.0293 (14)	0.0344 (15)	0.0033 (12)	0.0142 (13)	−0.0034 (11)
C5	0.0352 (14)	0.0308 (14)	0.0352 (14)	−0.0012 (11)	0.0161 (12)	−0.0010 (11)
C6	0.062 (2)	0.0393 (16)	0.0332 (15)	0.0090 (14)	0.0079 (14)	−0.0074 (12)
C7	0.078 (2)	0.0341 (16)	0.0464 (18)	0.0146 (15)	0.0143 (17)	−0.0095 (13)
C8	0.0328 (14)	0.0322 (14)	0.0296 (13)	−0.0024 (11)	0.0110 (11)	−0.0013 (11)
C9	0.0542 (18)	0.0412 (16)	0.0329 (15)	0.0086 (13)	0.0136 (14)	0.0004 (12)
C10	0.0381 (15)	0.0375 (15)	0.0276 (14)	−0.0018 (12)	0.0073 (12)	0.0015 (11)
C11	0.0504 (17)	0.0295 (14)	0.0328 (14)	0.0024 (12)	0.0133 (13)	0.0034 (12)
C12	0.068 (2)	0.0310 (15)	0.0343 (15)	0.0025 (13)	0.0120 (14)	−0.0003 (12)
C13	0.0489 (17)	0.0373 (15)	0.0390 (16)	0.0028 (13)	0.0190 (13)	−0.0011 (12)
C14	0.057 (2)	0.0430 (17)	0.0493 (18)	−0.0045 (14)	0.0162 (16)	−0.0057 (14)

Geometric parameters (Å, º)

S1—C10	1.731 (3)	C4—C5	1.390 (4)
S1—C9	1.808 (3)	C4—H4	0.9300
O1—C2	1.362 (3)	C5—C6	1.386 (4)
O1—C1	1.422 (4)	C5—C8	1.478 (4)
O2—C14	1.409 (4)	C6—C7	1.374 (4)
O2—H2	0.8200	C6—H6	0.9300
N1—C8	1.283 (3)	C7—H7	0.9300
N1—N2	1.393 (3)	C8—C9	1.510 (4)
N2—C11	1.365 (3)	C9—H9A	0.9700
N2—C10	1.367 (3)	C9—H9B	0.9700
N3—C10	1.297 (3)	C11—C12	1.491 (4)
N3—N4	1.403 (3)	C12—C13	1.518 (4)
N4—C11	1.299 (3)	C12—H12A	0.9700
C1—H1A	0.9600	C12—H12B	0.9700
C1—H1B	0.9600	C13—C14	1.514 (4)
C1—H1C	0.9600	C13—H13A	0.9700
C2—C3	1.379 (4)	C13—H13B	0.9700
C2—C7	1.386 (4)	C14—H14A	0.9700
C3—C4	1.379 (4)	C14—H14B	0.9700
C3—H3	0.9300
C10—S1—C9	95.36 (13)	N1—C8—C5	116.6 (2)
C2—O1—C1	118.0 (2)	N1—C8—C9	124.3 (2)
C14—O2—H2	109.4	C5—C8—C9	118.9 (2)
C8—N1—N2	116.2 (2)	C8—C9—S1	113.99 (19)
C11—N2—C10	105.4 (2)	C8—C9—H9A	108.8
C11—N2—N1	124.2 (2)	S1—C9—H9A	108.8
C10—N2—N1	129.8 (2)	C8—C9—H9B	108.8
C10—N3—N4	106.3 (2)	S1—C9—H9B	108.8
C11—N4—N3	108.2 (2)	H9A—C9—H9B	107.6
O1—C1—H1A	109.5	N3—C10—N2	110.7 (2)
O1—C1—H1B	109.5	N3—C10—S1	128.8 (2)
H1A—C1—H1B	109.5	N2—C10—S1	120.42 (19)
O1—C1—H1C	109.5	N4—C11—N2	109.4 (2)
H1A—C1—H1C	109.5	N4—C11—C12	127.0 (2)
H1B—C1—H1C	109.5	N2—C11—C12	123.6 (2)
O1—C2—C3	124.9 (3)	C11—C12—C13	112.7 (2)
O1—C2—C7	116.1 (2)	C11—C12—H12A	109.0
C3—C2—C7	119.0 (3)	C13—C12—H12A	109.0
C2—C3—C4	119.7 (2)	C11—C12—H12B	109.0
C2—C3—H3	120.1	C13—C12—H12B	109.0
C4—C3—H3	120.1	H12A—C12—H12B	107.8
C3—C4—C5	122.0 (2)	C14—C13—C12	111.7 (2)
C3—C4—H4	119.0	C14—C13—H13A	109.3
C5—C4—H4	119.0	C12—C13—H13A	109.3
C6—C5—C4	117.4 (2)	C14—C13—H13B	109.3
C6—C5—C8	122.5 (2)	C12—C13—H13B	109.3
C4—C5—C8	120.1 (2)	H13A—C13—H13B	107.9
C7—C6—C5	121.1 (3)	O2—C14—C13	112.8 (3)
C7—C6—H6	119.5	O2—C14—H14A	109.0
C5—C6—H6	119.5	C13—C14—H14A	109.0
C6—C7—C2	120.8 (3)	O2—C14—H14B	109.0
C6—C7—H7	119.6	C13—C14—H14B	109.0
C2—C7—H7	119.6	H14A—C14—H14B	107.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N4^i	0.82	2.08	2.892 (3)	173

Symmetry code: (i) −x+2, −y+1, −z+1.