2-(Tosyl­amino)butan-1-ol

In the title compound, C₁₁H₁₇NO₃S, the crystal packing is stabilized by O—H...O and N—H...O hydrogen bonds and inter­molecular π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.116
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_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
   2 ALERT level G = General alerts; check

   2 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
   1 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-(tosylamino)butan-1-ol

Crystal data

C11H17NO3S	Z = 2
Mr = 243.32	F(000) = 260
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4659 (4) Å	Cell parameters from 1375 reflections
b = 7.0150 (5) Å	θ = 3.0–25.0°
c = 14.2483 (9) Å	µ = 0.26 mm^−1
α = 101.720 (1)°	T = 293 K
β = 97.962 (1)°	Block, colorless
γ = 99.015 (1)°	0.26 × 0.25 × 0.21 mm
V = 615.22 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 28.0°, θmin = 3.0°
ω scans	h = −8→8
7043 measured reflections	k = −9→9
2810 independent reflections	l = −18→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.0989P] where P = (Fo^2 + 2Fc^2)/3
2810 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.29 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
C1	0.8688 (5)	0.8344 (4)	1.09134 (16)	0.1010 (9)
H1A	0.7822	0.8760	1.1383	0.152*
H1B	0.9626	0.9481	1.0834	0.152*
H1C	0.9511	0.7445	1.1136	0.152*
C2	0.7275 (3)	0.7311 (3)	0.99470 (12)	0.0668 (5)
C3	0.5207 (4)	0.7559 (2)	0.97604 (13)	0.0657 (5)
H3	0.4659	0.8325	1.0243	0.079*
C4	0.3916 (3)	0.6687 (2)	0.88634 (12)	0.0526 (3)
H4	0.2532	0.6903	0.8740	0.063*
C5	0.4704 (2)	0.5497 (2)	0.81586 (9)	0.0414 (3)
C6	0.6768 (2)	0.5181 (3)	0.83400 (12)	0.0572 (4)
H6	0.7296	0.4355	0.7872	0.069*
C7	0.8030 (3)	0.6114 (3)	0.92310 (14)	0.0680 (5)
H7	0.9427	0.5930	0.9351	0.082*
C8	0.3857 (2)	0.74592 (19)	0.61599 (10)	0.0417 (3)
H8	0.3487	0.8125	0.6771	0.050*
C9	0.2068 (2)	0.7411 (2)	0.53348 (10)	0.0444 (3)
H9A	0.0736	0.6719	0.5447	0.053*
H9B	0.1915	0.8753	0.5306	0.053*
C10	0.5975 (2)	0.8617 (2)	0.60420 (11)	0.0491 (3)
H10A	0.6466	0.7867	0.5494	0.059*
H10B	0.5745	0.9863	0.5890	0.059*
C11	0.7701 (3)	0.9051 (3)	0.69369 (14)	0.0715 (5)
H11A	0.7195	0.9718	0.7493	0.107*
H11B	0.8940	0.9881	0.6836	0.107*
H11C	0.8059	0.7829	0.7048	0.107*
N1	0.40513 (18)	0.54197 (16)	0.62258 (8)	0.0422 (3)
H1	0.4703	0.4765	0.5822	0.051*
O1	0.10298 (16)	0.48354 (19)	0.70791 (8)	0.0569 (3)
O2	0.3324 (2)	0.23450 (16)	0.67757 (9)	0.0599 (3)
O3	0.25579 (16)	0.64213 (17)	0.44431 (7)	0.0511 (3)
H3A	0.1475	0.6080	0.4028	0.077*
S1	0.31055 (5)	0.43745 (5)	0.70127 (2)	0.04199 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.128 (2)	0.0835 (15)	0.0618 (12)	−0.0342 (14)	−0.0331 (12)	0.0243 (11)
C2	0.0799 (12)	0.0587 (9)	0.0494 (9)	−0.0182 (8)	−0.0113 (8)	0.0234 (7)
C3	0.0928 (13)	0.0485 (8)	0.0477 (8)	0.0034 (8)	0.0072 (8)	0.0038 (7)
C4	0.0566 (8)	0.0489 (8)	0.0505 (8)	0.0092 (6)	0.0087 (6)	0.0085 (6)
C5	0.0394 (6)	0.0456 (7)	0.0387 (6)	0.0035 (5)	0.0041 (5)	0.0137 (5)
C6	0.0463 (8)	0.0840 (11)	0.0472 (8)	0.0184 (7)	0.0075 (6)	0.0246 (8)
C7	0.0466 (8)	0.0984 (14)	0.0595 (10)	0.0012 (8)	−0.0049 (7)	0.0383 (10)
C8	0.0452 (7)	0.0389 (6)	0.0385 (6)	0.0059 (5)	0.0040 (5)	0.0070 (5)
C9	0.0400 (6)	0.0469 (7)	0.0476 (7)	0.0097 (5)	0.0066 (5)	0.0132 (6)
C10	0.0483 (7)	0.0445 (7)	0.0467 (7)	−0.0038 (6)	−0.0022 (6)	0.0096 (6)
C11	0.0591 (10)	0.0742 (11)	0.0634 (11)	−0.0132 (8)	−0.0158 (8)	0.0127 (9)
N1	0.0474 (6)	0.0418 (6)	0.0384 (5)	0.0087 (5)	0.0091 (4)	0.0102 (4)
O1	0.0355 (5)	0.0794 (8)	0.0529 (6)	0.0033 (5)	0.0033 (4)	0.0172 (5)
O2	0.0775 (8)	0.0408 (5)	0.0579 (6)	0.0011 (5)	0.0109 (5)	0.0119 (5)
O3	0.0395 (5)	0.0681 (7)	0.0407 (5)	0.0084 (4)	−0.0009 (4)	0.0081 (5)
S1	0.0395 (2)	0.0437 (2)	0.0398 (2)	0.00121 (13)	0.00299 (13)	0.01052 (14)

Geometric parameters (Å, º)

C1—C2	1.515 (2)	C8—C10	1.5278 (19)
C1—H1A	0.9600	C8—H8	0.9800
C1—H1B	0.9600	C9—O3	1.421 (2)
C1—H1C	0.9600	C9—H9A	0.9700
C2—C3	1.371 (3)	C9—H9B	0.9700
C2—C7	1.379 (3)	C10—C11	1.519 (2)
C3—C4	1.390 (2)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.378 (2)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—C6	1.385 (2)	C11—H11C	0.9600
C5—S1	1.7634 (13)	N1—S1	1.598 (1)
C6—C7	1.384 (2)	N1—H1	0.8600
C6—H6	0.9300	O1—S1	1.440 (1)
C7—H7	0.9300	O2—S1	1.429 (1)
C8—N1	1.476 (2)	O3—H3A	0.8200
C8—C9	1.5220 (19)
C2—C1—H1A	109.5	C10—C8—H8	108.0
C2—C1—H1B	109.5	O3—C9—C8	108.89 (11)
H1A—C1—H1B	109.5	O3—C9—H9A	109.9
C2—C1—H1C	109.5	C8—C9—H9A	109.9
H1A—C1—H1C	109.5	O3—C9—H9B	109.9
H1B—C1—H1C	109.5	C8—C9—H9B	109.9
C3—C2—C7	118.31 (15)	H9A—C9—H9B	108.3
C3—C2—C1	120.5 (2)	C11—C10—C8	113.85 (13)
C7—C2—C1	121.2 (2)	C11—C10—H10A	108.8
C2—C3—C4	121.26 (17)	C8—C10—H10A	108.8
C2—C3—H3	119.4	C11—C10—H10B	108.8
C4—C3—H3	119.4	C8—C10—H10B	108.8
C5—C4—C3	119.40 (16)	H10A—C10—H10B	107.7
C5—C4—H4	120.3	C10—C11—H11A	109.5
C3—C4—H4	120.3	C10—C11—H11B	109.5
C4—C5—C6	120.35 (14)	H11A—C11—H11B	109.5
C4—C5—S1	120.45 (11)	C10—C11—H11C	109.5
C6—C5—S1	119.20 (12)	H11A—C11—H11C	109.5
C7—C6—C5	118.76 (16)	H11B—C11—H11C	109.5
C7—C6—H6	120.6	C8—N1—S1	123.0 (1)
C5—C6—H6	120.6	C8—N1—H1	118.5
C2—C7—C6	121.86 (17)	S1—N1—H1	118.5
C2—C7—H7	119.1	C9—O3—H3A	109.5
C6—C7—H7	119.1	O2—S1—O1	119.2 (1)
N1—C8—C9	110.09 (11)	O2—S1—N1	107.4 (1)
N1—C8—C10	110.63 (11)	O1—S1—N1	108.3 (1)
C9—C8—C10	111.98 (11)	O2—S1—C5	107.8 (1)
N1—C8—H8	108.0	O1—S1—C5	105.9 (1)
C9—C8—H8	108.0	N1—S1—C5	107.7 (1)
C7—C2—C3—C4	−2.1 (3)	C9—C8—C10—C11	168.70 (14)
C1—C2—C3—C4	177.37 (17)	C9—C8—N1—S1	−100.7 (1)
C2—C3—C4—C5	2.1 (3)	C10—C8—N1—S1	135.0 (1)
C3—C4—C5—C6	−0.3 (2)	C8—N1—S1—O2	172.04 (10)
C3—C4—C5—S1	−179.88 (12)	C8—N1—S1—O1	42.10 (12)
C4—C5—C6—C7	−1.5 (2)	C8—N1—S1—C5	−72.1 (1)
S1—C5—C6—C7	178.14 (13)	C4—C5—S1—O2	−133.92 (13)
C3—C2—C7—C6	0.3 (3)	C6—C5—S1—O2	46.48 (14)
C1—C2—C7—C6	−179.18 (17)	C4—C5—S1—O1	−5.28 (14)
C5—C6—C7—C2	1.5 (3)	C6—C5—S1—O1	175.12 (12)
N1—C8—C9—O3	−61.34 (14)	C4—C5—S1—N1	110.5 (1)
C10—C8—C9—O3	62.18 (15)	C6—C5—S1—N1	−69.1 (1)
N1—C8—C10—C11	−68.08 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.49	2.867 (2)	105
O3—H3A···O1^i	0.82	2.02	2.837 (2)	175
N1—H1···O3^ii	0.86	2.12	2.890 (2)	149

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