1-(1,3-Benzothia­zol-2-yl)propan-2-ol

In the title compound, C₁₀H₁₁NOS, the asymmetric unit contains two mol­ecules. The structure is stabilized by an inter­molecular O—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.118
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C9      ..       5.13 su
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   3 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(1,3-Benzothiazol-2-yl)propan-2-ol

Crystal data

C10H11NOS	F(000) = 816
Mr = 193.27	Dx = 1.326 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2240 reflections
a = 15.7702 (11) Å	θ = 1.7–27.2°
b = 7.8856 (4) Å	µ = 0.29 mm^−1
c = 15.8703 (11) Å	T = 296 K
β = 101.135 (5)°	Prism, pale yellow
V = 1936.4 (2) Å^3	0.68 × 0.56 × 0.43 mm
Z = 8

Data collection

Stoe IPDS-II diffractometer	4258 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3250 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.043
Detector resolution: 6.67 pixels mm^-1	θmax = 27.1°, θmin = 1.7°
ω scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.826, Tmax = 0.885	l = −20→18
17123 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.2309P] where P = (Fo^2 + 2Fc^2)/3
4258 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.32 e Å^−3
2 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.18127 (3)	0.10546 (6)	0.28014 (3)	0.0542 (1)
O1	0.07658 (9)	0.09987 (18)	0.41205 (9)	0.0642 (4)
N1	0.08596 (9)	0.28209 (19)	0.16132 (9)	0.0519 (5)
C1	0.22502 (11)	0.1627 (2)	0.19236 (11)	0.0490 (5)
C2	0.30722 (12)	0.1299 (3)	0.17535 (13)	0.0590 (6)
C3	0.32610 (13)	0.1909 (3)	0.10017 (14)	0.0655 (7)
C4	0.26575 (14)	0.2828 (3)	0.04226 (13)	0.0664 (7)
C5	0.18496 (13)	0.3161 (3)	0.05865 (12)	0.0602 (6)
C6	0.16431 (11)	0.2560 (2)	0.13473 (11)	0.0491 (5)
C7	0.08656 (11)	0.2121 (2)	0.23534 (10)	0.0495 (5)
C8	0.01102 (12)	0.2203 (3)	0.27915 (11)	0.0595 (6)
C9	0.03257 (13)	0.2468 (3)	0.37487 (12)	0.0602 (6)
C10	−0.04725 (18)	0.2791 (4)	0.41193 (16)	0.0950 (10)
S2	0.29327 (4)	0.43417 (8)	0.65498 (4)	0.0724 (2)
O2	0.41827 (9)	0.14528 (18)	0.56104 (9)	0.0631 (5)
N2	0.18180 (10)	0.2370 (2)	0.56476 (9)	0.0551 (5)
C11	0.20449 (12)	0.3772 (2)	0.69804 (12)	0.0574 (6)
C12	0.18186 (16)	0.4225 (3)	0.77549 (14)	0.0713 (8)
C13	0.10616 (17)	0.3615 (3)	0.79323 (14)	0.0754 (8)
C14	0.05238 (15)	0.2576 (3)	0.73574 (15)	0.0716 (8)
C15	0.07439 (13)	0.2112 (3)	0.65936 (13)	0.0634 (7)
C16	0.15138 (11)	0.2713 (2)	0.63985 (11)	0.0518 (5)
C17	0.25361 (12)	0.3131 (3)	0.56409 (12)	0.0578 (6)
C18	0.29949 (13)	0.3046 (3)	0.49012 (13)	0.0674 (7)
C19	0.39659 (13)	0.2959 (3)	0.51236 (13)	0.0639 (7)
C20	0.43577 (16)	0.2956 (4)	0.43281 (16)	0.0876 (10)
H1	0.1108 (19)	0.133 (4)	0.4670 (16)	0.125 (11)*
H2	0.34780	0.06860	0.21380	0.0710*
H3	0.38040	0.17040	0.08760	0.0790*
H4	0.28030	0.32230	−0.00830	0.0800*
H5	0.14490	0.37750	0.01970	0.0720*
H8A	−0.02140	0.11560	0.26770	0.0710*
H8B	−0.02640	0.31200	0.25380	0.0710*
H9	0.07130	0.34460	0.38730	0.0720*
H10A	−0.07710	0.37660	0.38470	0.1420*
H10B	−0.03080	0.29920	0.47250	0.1420*
H10C	−0.08460	0.18200	0.40210	0.1420*
H11	0.4740 (14)	0.159 (3)	0.5843 (17)	0.095 (8)*
H12	0.21740	0.49260	0.81420	0.0860*
H13	0.09030	0.39020	0.84490	0.0910*
H14	0.00080	0.21900	0.74910	0.0860*
H15	0.03840	0.14070	0.62120	0.0760*
H18A	0.28340	0.40370	0.45430	0.0810*
H18B	0.27870	0.20570	0.45600	0.0810*
H19	0.41840	0.39410	0.54780	0.0770*
H20A	0.41470	0.19960	0.39780	0.1310*
H20B	0.49760	0.28920	0.44910	0.1310*
H20C	0.42000	0.39810	0.40090	0.1310*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0511 (2)	0.0640 (3)	0.0452 (2)	0.0084 (2)	0.0039 (2)	0.0089 (2)
O1	0.0642 (8)	0.0715 (8)	0.0539 (7)	0.0044 (7)	0.0043 (6)	0.0015 (6)
N1	0.0471 (8)	0.0606 (9)	0.0449 (7)	0.0019 (6)	0.0010 (6)	0.0050 (6)
C1	0.0480 (9)	0.0504 (9)	0.0464 (9)	−0.0009 (7)	0.0033 (7)	−0.0022 (7)
C2	0.0509 (10)	0.0647 (11)	0.0602 (11)	0.0043 (9)	0.0079 (8)	−0.0009 (9)
C3	0.0554 (11)	0.0741 (12)	0.0690 (12)	−0.0032 (10)	0.0173 (9)	−0.0036 (10)
C4	0.0692 (13)	0.0763 (13)	0.0567 (11)	−0.0104 (10)	0.0193 (9)	0.0021 (10)
C5	0.0617 (11)	0.0678 (12)	0.0492 (10)	−0.0029 (9)	0.0061 (8)	0.0094 (9)
C6	0.0478 (9)	0.0524 (9)	0.0454 (8)	−0.0027 (7)	0.0048 (7)	0.0002 (7)
C7	0.0473 (9)	0.0557 (10)	0.0425 (8)	−0.0003 (7)	0.0011 (7)	0.0000 (7)
C8	0.0494 (10)	0.0758 (12)	0.0520 (10)	0.0060 (9)	0.0063 (8)	0.0065 (9)
C9	0.0630 (11)	0.0654 (11)	0.0530 (10)	0.0086 (9)	0.0134 (8)	0.0051 (9)
C10	0.0975 (19)	0.120 (2)	0.0762 (15)	0.0432 (17)	0.0385 (14)	0.0162 (15)
S2	0.0609 (3)	0.0779 (4)	0.0718 (3)	−0.0158 (3)	−0.0037 (2)	−0.0089 (3)
O2	0.0543 (8)	0.0663 (8)	0.0623 (8)	−0.0049 (6)	−0.0049 (6)	0.0113 (6)
N2	0.0494 (8)	0.0610 (9)	0.0506 (8)	0.0035 (7)	−0.0013 (6)	−0.0050 (7)
C11	0.0579 (10)	0.0523 (10)	0.0558 (10)	0.0043 (8)	−0.0047 (8)	−0.0065 (8)
C12	0.0876 (16)	0.0623 (12)	0.0585 (11)	0.0051 (11)	0.0003 (11)	−0.0145 (9)
C13	0.0944 (17)	0.0737 (14)	0.0592 (12)	0.0234 (13)	0.0175 (11)	−0.0040 (10)
C14	0.0641 (12)	0.0803 (14)	0.0728 (13)	0.0108 (11)	0.0190 (10)	0.0047 (11)
C15	0.0560 (11)	0.0668 (12)	0.0635 (11)	−0.0013 (9)	0.0017 (9)	−0.0035 (9)
C16	0.0505 (9)	0.0505 (9)	0.0506 (9)	0.0057 (7)	0.0004 (7)	−0.0037 (7)
C17	0.0515 (10)	0.0624 (11)	0.0545 (10)	0.0065 (8)	−0.0020 (8)	0.0042 (8)
C18	0.0586 (11)	0.0832 (14)	0.0569 (11)	0.0062 (10)	0.0025 (9)	0.0108 (10)
C19	0.0600 (11)	0.0651 (12)	0.0650 (12)	−0.0023 (9)	0.0082 (9)	0.0128 (9)
C20	0.0774 (15)	0.1073 (19)	0.0823 (16)	0.0123 (14)	0.0259 (13)	0.0288 (14)

Geometric parameters (Å, º)

S1—C1	1.7297 (18)	C8—H8A	0.9700
S1—C7	1.7416 (18)	C8—H8B	0.9700
S2—C11	1.732 (2)	C9—H9	0.9800
S2—C17	1.742 (2)	C10—H10B	0.9600
O1—C9	1.419 (3)	C10—H10A	0.9600
O1—H1	0.97 (3)	C10—H10C	0.9600
O2—C19	1.422 (3)	C11—C12	1.391 (3)
O2—H11	0.89 (2)	C11—C16	1.398 (2)
N1—C6	1.396 (2)	C12—C13	1.366 (4)
N1—C7	1.296 (2)	C13—C14	1.387 (3)
N2—C16	1.394 (2)	C14—C15	1.373 (3)
N2—C17	1.284 (3)	C15—C16	1.393 (3)
C1—C2	1.398 (3)	C17—C18	1.495 (3)
C1—C6	1.399 (2)	C18—C19	1.505 (3)
C2—C3	1.371 (3)	C19—C20	1.509 (3)
C3—C4	1.392 (3)	C12—H12	0.9300
C4—C5	1.374 (3)	C13—H13	0.9300
C5—C6	1.393 (3)	C14—H14	0.9300
C7—C8	1.492 (3)	C15—H15	0.9300
C8—C9	1.506 (3)	C18—H18A	0.9700
C9—C10	1.510 (4)	C18—H18B	0.9700
C2—H2	0.9300	C19—H19	0.9800
C3—H3	0.9300	C20—H20A	0.9600
C4—H4	0.9300	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
S1···O1	2.9061 (15)	C17···H1	2.85 (3)
S1···N1	2.5808 (15)	H1···N2	1.91 (3)
S2···N2	2.5662 (17)	H1···C16	2.91 (3)
S1···H18B	3.0200	H1···C17	2.85 (3)
S2···H19	2.8600	H2···C7^iv	3.0500
S2···H8A^i	3.1400	H3···H10B^ix	2.5200
O1···N2	2.871 (2)	H5···O2^vii	2.5700
O1···S1	2.9061 (15)	H8A···C15^iii	3.0100
O2···C13^ii	3.294 (3)	H8A···S2^v	3.1400
O2···N1^i	2.869 (2)	H8A···C14^iii	2.9800
O1···H15^iii	2.6100	H8A···H10C	2.5800
O2···H13^ii	2.5200	H8B···C13^viii	2.9000
O2···H5^iv	2.5700	H8B···H10A	2.4200
N1···O2^v	2.869 (2)	H10A···H8B	2.4200
N1···S1	2.5808 (15)	H10A···C16^viii	3.0100
N2···O1	2.871 (2)	H10A···C11^viii	2.9200
N2···S2	2.5662 (17)	H10B···H3^x	2.5200
N2···C9	3.448 (2)	H10C···H8A	2.5800
N1···H11^v	2.00 (2)	H11···H20B	2.4700
N2···H1	1.91 (3)	H11···N1^i	2.00 (2)
C9···N2	3.448 (2)	H11···C6^i	3.03 (2)
C13···O2^vi	3.294 (3)	H11···C7^i	2.88 (3)
C1···H18A^iv	3.0800	H12···C16^vi	3.0100
C2···H18A^iv	2.8800	H13···O2^vi	2.5200
C3···H18A^iv	2.8800	H15···O1^iii	2.6100
C4···H18A^iv	3.0900	H18A···H20C	2.4600
C6···H11^v	3.03 (2)	H18A···C1^vii	3.0800
C7···H11^v	2.88 (3)	H18A···C2^vii	2.8800
C7···H2^vii	3.0500	H18A···C3^vii	2.8800
C11···H10A^viii	2.9200	H18A···C4^vii	3.0900
C13···H8B^viii	2.9000	H18B···S1	3.0200
C14···H8A^iii	2.9800	H18B···H20A	2.4900
C15···H8A^iii	3.0100	H19···S2	2.8600
C16···H10A^viii	3.0100	H20A···H18B	2.4900
C16···H1	2.91 (3)	H20B···H11	2.4700
C16···H12^ii	3.0100	H20C···H18A	2.4600
C1—S1—C7	89.38 (8)	H10B—C10—H10C	109.00
C11—S2—C17	89.78 (9)	C9—C10—H10A	109.00
C9—O1—H1	107.3 (18)	H10A—C10—H10B	109.00
C19—O2—H11	103.8 (16)	S2—C11—C12	130.32 (16)
C6—N1—C7	111.05 (15)	S2—C11—C16	108.74 (13)
C16—N2—C17	111.48 (15)	C12—C11—C16	120.93 (18)
S1—C1—C6	109.56 (13)	C11—C12—C13	118.4 (2)
C2—C1—C6	120.94 (17)	C12—C13—C14	121.3 (2)
S1—C1—C2	129.50 (14)	C13—C14—C15	120.8 (2)
C1—C2—C3	117.92 (19)	C14—C15—C16	119.0 (2)
C2—C3—C4	121.4 (2)	N2—C16—C15	125.63 (16)
C3—C4—C5	121.01 (19)	C11—C16—C15	119.56 (17)
C4—C5—C6	118.66 (19)	N2—C16—C11	114.80 (16)
N1—C6—C5	125.50 (16)	S2—C17—C18	121.60 (15)
N1—C6—C1	114.45 (15)	N2—C17—C18	123.18 (18)
C1—C6—C5	120.05 (17)	S2—C17—N2	115.19 (14)
N1—C7—C8	122.48 (16)	C17—C18—C19	116.28 (17)
S1—C7—C8	121.98 (12)	O2—C19—C20	111.03 (19)
S1—C7—N1	115.54 (13)	C18—C19—C20	111.49 (18)
C7—C8—C9	115.54 (16)	O2—C19—C18	107.00 (17)
O1—C9—C10	110.68 (18)	C11—C12—H12	121.00
C8—C9—C10	111.94 (18)	C13—C12—H12	121.00
O1—C9—C8	107.65 (17)	C12—C13—H13	119.00
C3—C2—H2	121.00	C14—C13—H13	119.00
C1—C2—H2	121.00	C13—C14—H14	120.00
C2—C3—H3	119.00	C15—C14—H14	120.00
C4—C3—H3	119.00	C14—C15—H15	120.00
C5—C4—H4	119.00	C16—C15—H15	120.00
C3—C4—H4	120.00	C17—C18—H18A	108.00
C4—C5—H5	121.00	C17—C18—H18B	108.00
C6—C5—H5	121.00	C19—C18—H18A	108.00
C9—C8—H8B	108.00	C19—C18—H18B	108.00
C7—C8—H8B	108.00	H18A—C18—H18B	107.00
C7—C8—H8A	108.00	O2—C19—H19	109.00
H8A—C8—H8B	107.00	C18—C19—H19	109.00
C9—C8—H8A	108.00	C20—C19—H19	109.00
C8—C9—H9	109.00	C19—C20—H20A	109.00
O1—C9—H9	109.00	C19—C20—H20B	109.00
C10—C9—H9	109.00	C19—C20—H20C	109.00
C9—C10—H10B	109.00	H20A—C20—H20B	110.00
C9—C10—H10C	109.00	H20A—C20—H20C	109.00
H10A—C10—H10C	109.00	H20B—C20—H20C	109.00
C7—S1—C1—C2	178.29 (19)	C2—C3—C4—C5	0.2 (4)
C7—S1—C1—C6	−0.99 (13)	C3—C4—C5—C6	0.0 (3)
C1—S1—C7—C8	−179.63 (16)	C4—C5—C6—C1	−0.5 (3)
C1—S1—C7—N1	1.00 (14)	C4—C5—C6—N1	178.65 (19)
C17—S2—C11—C12	−179.3 (2)	S1—C7—C8—C9	40.5 (2)
C11—S2—C17—N2	−0.11 (17)	N1—C7—C8—C9	−140.15 (19)
C17—S2—C11—C16	−0.29 (14)	C7—C8—C9—O1	−66.5 (2)
C11—S2—C17—C18	178.03 (19)	C7—C8—C9—C10	171.6 (2)
C6—N1—C7—C8	179.96 (17)	S2—C11—C16—C15	−178.64 (15)
C6—N1—C7—S1	−0.67 (18)	S2—C11—C16—N2	0.63 (19)
C7—N1—C6—C5	−179.32 (18)	C12—C11—C16—N2	179.74 (17)
C7—N1—C6—C1	−0.1 (2)	C12—C11—C16—C15	0.5 (3)
C16—N2—C17—C18	−177.63 (19)	S2—C11—C12—C13	178.62 (17)
C16—N2—C17—S2	0.5 (2)	C16—C11—C12—C13	−0.3 (3)
C17—N2—C16—C15	178.5 (2)	C11—C12—C13—C14	−0.4 (4)
C17—N2—C16—C11	−0.7 (2)	C12—C13—C14—C15	0.8 (4)
C2—C1—C6—N1	−178.49 (17)	C13—C14—C15—C16	−0.6 (3)
C6—C1—C2—C3	−0.5 (3)	C14—C15—C16—C11	0.0 (3)
S1—C1—C6—C5	−179.91 (15)	C14—C15—C16—N2	−179.22 (19)
S1—C1—C6—N1	0.86 (18)	S2—C17—C18—C19	39.7 (3)
S1—C1—C2—C3	−179.71 (16)	N2—C17—C18—C19	−142.3 (2)
C2—C1—C6—C5	0.7 (3)	C17—C18—C19—O2	60.9 (2)
C1—C2—C3—C4	0.0 (3)	C17—C18—C19—C20	−177.5 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.97 (3)	1.91 (3)	2.871 (2)	169 (3)