2-(Hydroxy­meth­yl)-1,2-benzothia­zol-3(2H)-one

In the title compound, C₈H₇NO₂S, the benzisothia­zolone ring system is planar, with a maximum deviation from the mean plane of 0.038 (2) Å for the N atom. Weak inter­molecular hydrogen bonds and a π–π stacking inter­action stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.058
• wR factor = 0.105
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-(Hydroxymethyl)-1,2-benzothiazol-3(2H)-one

Crystal data

C8H7NO2S	Dx = 1.517 Mg m^−3
Mr = 181.21	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 25 reflections
Hall symbol: -I 4ad	θ = 4–14°
a = 17.856 (7) Å	µ = 0.36 mm^−1
c = 9.955 (2) Å	T = 293 K
V = 3174.0 (19) Å^3	Block, colourless
Z = 16	0.25 × 0.20 × 0.18 mm
F(000) = 1504

Data collection

Enraf–Nonius CAD-4 diffractometer	1365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −22→22
Tmin = 0.915, Tmax = 0.942	l = 0→11
6764 measured reflections	3 standard reflections every 100 reflections
1704 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0408P)^2 + 0.6111P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1704 reflections	Δρmax = 0.29 e Å^−3
110 parameters	Δρmin = −0.99 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (5)

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	−0.01025 (2)	0.11419 (2)	0.12334 (5)	0.04674 (19)
O1	0.06724 (8)	0.08761 (9)	0.42000 (13)	0.0650 (4)
H1A	0.1128	0.0874	0.4102	0.097*
O2	0.14645 (8)	−0.02828 (7)	0.16187 (13)	0.0540 (4)
N1	0.04400 (9)	0.04672 (8)	0.19722 (13)	0.0439 (4)
C1	0.03993 (10)	0.10531 (9)	−0.02487 (17)	0.0406 (4)
C2	0.02821 (12)	0.14419 (10)	−0.14524 (19)	0.0517 (5)
H2A	−0.0107	0.1785	−0.1540	0.062*
C3	0.07628 (14)	0.12975 (11)	−0.25013 (19)	0.0603 (5)
H3A	0.0692	0.1547	−0.3312	0.072*
C4	0.13541 (13)	0.07883 (11)	−0.2389 (2)	0.0588 (5)
H4A	0.1671	0.0709	−0.3117	0.071*
C5	0.14708 (11)	0.04030 (11)	−0.12068 (18)	0.0485 (4)
H5A	0.1864	0.0064	−0.1127	0.058*
C6	0.09833 (10)	0.05344 (9)	−0.01292 (16)	0.0390 (4)
C7	0.10122 (9)	0.01855 (9)	0.12034 (16)	0.0408 (4)
C8	0.03552 (12)	0.03202 (12)	0.34027 (17)	0.0532 (5)
H8A	−0.0174	0.0280	0.3613	0.064*
H8B	0.0589	−0.0156	0.3615	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0411 (3)	0.0424 (3)	0.0567 (3)	0.00230 (16)	0.0075 (2)	−0.00037 (19)
O1	0.0545 (8)	0.0875 (11)	0.0529 (7)	−0.0075 (7)	0.0012 (7)	−0.0216 (8)
O2	0.0602 (8)	0.0452 (7)	0.0567 (7)	0.0100 (6)	−0.0042 (7)	0.0008 (6)
N1	0.0483 (8)	0.0413 (7)	0.0422 (7)	0.0000 (6)	0.0035 (7)	0.0003 (6)
C1	0.0416 (8)	0.0349 (8)	0.0452 (8)	−0.0072 (6)	−0.0026 (7)	−0.0047 (7)
C2	0.0576 (11)	0.0425 (9)	0.0550 (10)	−0.0026 (8)	−0.0095 (9)	0.0044 (8)
C3	0.0845 (15)	0.0534 (11)	0.0429 (9)	−0.0113 (10)	−0.0058 (10)	0.0064 (9)
C4	0.0757 (14)	0.0551 (11)	0.0455 (10)	−0.0118 (10)	0.0117 (10)	−0.0080 (9)
C5	0.0525 (10)	0.0463 (10)	0.0467 (9)	−0.0020 (8)	0.0050 (8)	−0.0111 (8)
C6	0.0426 (8)	0.0345 (8)	0.0401 (8)	−0.0052 (6)	−0.0007 (7)	−0.0080 (7)
C7	0.0423 (8)	0.0355 (8)	0.0447 (8)	−0.0028 (7)	−0.0034 (7)	−0.0064 (7)
C8	0.0555 (11)	0.0601 (12)	0.0440 (9)	−0.0097 (9)	0.0050 (9)	0.0013 (9)

Geometric parameters (Å, º)

S1—N1	1.7119 (17)	C3—C4	1.398 (3)
S1—C1	1.7335 (18)	C3—H3A	0.9300
O1—C8	1.391 (2)	C4—C5	1.379 (3)
O1—H1A	0.8200	C4—H4A	0.9300
O2—C7	1.234 (2)	C5—C6	1.401 (2)
N1—C7	1.372 (2)	C5—H5A	0.9300
N1—C8	1.456 (2)	C6—C7	1.467 (2)
C1—C6	1.400 (3)	C7—O2	1.234 (2)
C1—C2	1.401 (2)	C8—H8A	0.9700
C2—C3	1.376 (3)	C8—H8B	0.9700
C2—H2A	0.9300
N1—S1—C1	90.51 (8)	C4—C5—C6	118.42 (19)
C8—O1—H1A	109.5	C4—C5—H5A	120.8
C7—N1—C8	123.83 (16)	C6—C5—H5A	120.8
C7—N1—S1	116.09 (11)	C1—C6—C5	120.57 (16)
C8—N1—S1	119.23 (13)	C1—C6—C7	112.60 (15)
C6—C1—C2	120.80 (17)	C5—C6—C7	126.83 (16)
C6—C1—S1	111.91 (13)	O2—C7—N1	123.30 (15)
C2—C1—S1	127.28 (14)	O2—C7—N1	123.30 (15)
C3—C2—C1	117.59 (18)	O2—C7—C6	127.89 (16)
C3—C2—H2A	121.2	O2—C7—C6	127.89 (16)
C1—C2—H2A	121.2	N1—C7—C6	108.81 (14)
C2—C3—C4	122.18 (18)	O1—C8—N1	112.77 (15)
C2—C3—H3A	118.9	O1—C8—H8A	109.0
C4—C3—H3A	118.9	N1—C8—H8A	109.0
C5—C4—C3	120.45 (19)	O1—C8—H8B	109.0
C5—C4—H4A	119.8	N1—C8—H8B	109.0
C3—C4—H4A	119.8	H8A—C8—H8B	107.8
C1—S1—N1—C7	2.77 (13)	C8—N1—C7—O2	7.9 (3)
C1—S1—N1—C8	172.64 (14)	S1—N1—C7—O2	177.29 (14)
N1—S1—C1—C6	−2.26 (13)	C8—N1—C7—O2	7.9 (3)
N1—S1—C1—C2	179.03 (16)	S1—N1—C7—O2	177.29 (14)
C6—C1—C2—C3	−0.3 (3)	C8—N1—C7—C6	−171.76 (16)
S1—C1—C2—C3	178.27 (14)	S1—N1—C7—C6	−2.41 (17)
C1—C2—C3—C4	−0.5 (3)	C1—C6—C7—O2	−179.08 (17)
C2—C3—C4—C5	0.7 (3)	C5—C6—C7—O2	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C1—C6—C7—O2	−179.08 (17)
C2—C1—C6—C5	1.1 (3)	C5—C6—C7—O2	0.0 (3)
S1—C1—C6—C5	−177.74 (12)	C1—C6—C7—N1	0.60 (19)
C2—C1—C6—C7	−179.84 (15)	C5—C6—C7—N1	179.64 (16)
S1—C1—C6—C7	1.36 (18)	C7—N1—C8—O1	94.6 (2)
C4—C5—C6—C1	−0.9 (3)	S1—N1—C8—O1	−74.5 (2)
C4—C5—C6—C7	−179.87 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^i	0.82	1.97	2.774 (2)	169
C5—H5A···O2^ii	0.93	2.57	3.492 (3)	171

Symmetry codes: (i) y+1/4, −x+1/4, z+1/4; (ii) −y+1/4, x−1/4, z−1/4.