3-Hydr­oxy-N,N-dimethyl-3-(2-thien­yl)propanamine

The title compound, C₉H₁₅NOS, was prepared by the reduction of 2-thienyl 2-(dimethyl­amino)ethyl ketone hydro­chloride with sodium borohydride. In the crystal structure, O—H...N hydrogen bonds link pairs of mol­ecules into centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       5.37 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); 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 1997); software used to prepare material for publication: SHELXTL.

3-Hydroxy-N,N-dimethyl-3-(2-thienyl)propanamine

Crystal data

C9H15NOS	Z = 2
Mr = 185.28	F(000) = 200
Triclinic, P1	Dx = 1.238 Mg m^−3
Hall symbol: -P 1	Melting point: 72 K
a = 6.0670 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6467 (17) Å	Cell parameters from 1735 reflections
c = 11.678 (3) Å	θ = 2.8–26.3°
α = 96.004 (4)°	µ = 0.28 mm^−1
β = 104.036 (3)°	T = 294 K
γ = 105.835 (3)°	Block, colorless
V = 497.11 (19) Å^3	0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1726 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→6
Tmin = 0.936, Tmax = 0.951	k = −9→8
2505 measured reflections	l = −7→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.2073P] where P = (Fo^2 + 2Fc^2)/3
1726 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.30 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	0.35251 (9)	0.82014 (8)	0.66420 (5)	0.0566 (2)
N1	0.8591 (3)	0.6573 (2)	1.18681 (13)	0.0387 (4)
O1	0.3229 (2)	0.72991 (19)	0.90804 (12)	0.0432 (3)
H1	0.283 (4)	0.6152 (14)	0.8841 (19)	0.052 (6)*
C1	0.4888 (4)	0.7829 (3)	0.55696 (19)	0.0615 (6)
H1A	0.4280	0.7871	0.4765	0.074*
C2	0.6940 (4)	0.7466 (3)	0.60159 (18)	0.0558 (5)
H2	0.7918	0.7233	0.5556	0.067*
C3	0.7449 (3)	0.7479 (3)	0.72740 (16)	0.0417 (4)
H3	0.8802	0.7257	0.7725	0.050*
C4	0.5742 (3)	0.7853 (2)	0.77489 (16)	0.0366 (4)
C5	0.5612 (3)	0.8076 (2)	0.90226 (16)	0.0369 (4)
H5	0.6091	0.9405	0.9333	0.044*
C6	0.7360 (3)	0.7296 (3)	0.98200 (16)	0.0393 (4)
H6A	0.6895	0.5969	0.9554	0.047*
H6B	0.8946	0.7831	0.9738	0.047*
C7	0.7429 (3)	0.7702 (3)	1.11331 (16)	0.0409 (4)
H7A	0.8282	0.9000	1.1454	0.049*
H7B	0.5808	0.7470	1.1189	0.049*
C8	1.1123 (3)	0.7003 (3)	1.19142 (19)	0.0495 (5)
H8A	1.1932	0.8285	1.2253	0.074*
H8B	1.1263	0.6749	1.1117	0.074*
H8C	1.1831	0.6254	1.2403	0.074*
C9	0.8357 (4)	0.6885 (3)	1.30837 (18)	0.0561 (5)
H9A	0.9032	0.6093	1.3546	0.084*
H9B	0.6698	0.6614	1.3048	0.084*
H9C	0.9188	0.8153	1.3456	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0442 (3)	0.0737 (4)	0.0543 (3)	0.0249 (3)	0.0073 (2)	0.0198 (3)
N1	0.0371 (8)	0.0416 (8)	0.0353 (8)	0.0095 (6)	0.0098 (6)	0.0064 (6)
O1	0.0338 (7)	0.0482 (8)	0.0513 (8)	0.0149 (6)	0.0168 (6)	0.0080 (6)
C1	0.0625 (14)	0.0762 (15)	0.0397 (11)	0.0149 (11)	0.0076 (10)	0.0181 (10)
C2	0.0544 (12)	0.0751 (15)	0.0423 (11)	0.0224 (11)	0.0189 (10)	0.0108 (10)
C3	0.0410 (10)	0.0479 (10)	0.0396 (10)	0.0181 (8)	0.0116 (8)	0.0103 (8)
C4	0.0335 (9)	0.0341 (9)	0.0401 (9)	0.0084 (7)	0.0076 (7)	0.0094 (7)
C5	0.0336 (9)	0.0347 (9)	0.0434 (10)	0.0116 (7)	0.0114 (7)	0.0071 (7)
C6	0.0344 (9)	0.0461 (10)	0.0405 (10)	0.0153 (8)	0.0125 (8)	0.0089 (8)
C7	0.0386 (9)	0.0468 (10)	0.0380 (10)	0.0162 (8)	0.0098 (8)	0.0051 (8)
C8	0.0379 (10)	0.0509 (11)	0.0571 (12)	0.0139 (8)	0.0074 (9)	0.0131 (9)
C9	0.0636 (13)	0.0633 (13)	0.0395 (11)	0.0161 (11)	0.0147 (10)	0.0098 (9)

Geometric parameters (Å, º)

S1—C1	1.700 (2)	C5—C6	1.526 (2)
S1—C4	1.7248 (18)	C5—H5	0.9800
N1—C9	1.462 (2)	C6—C7	1.520 (2)
N1—C8	1.467 (2)	C6—H6A	0.9700
N1—C7	1.474 (2)	C6—H6B	0.9700
O1—C5	1.427 (2)	C7—H7A	0.9700
O1—H1	0.841 (10)	C7—H7B	0.9700
C1—C2	1.343 (3)	C8—H8A	0.9600
C1—H1A	0.9300	C8—H8B	0.9600
C2—C3	1.424 (3)	C8—H8C	0.9600
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.367 (3)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.503 (3)
C1—S1—C4	92.22 (10)	C7—C6—H6A	109.2
C9—N1—C8	109.83 (15)	C5—C6—H6A	109.2
C9—N1—C7	109.72 (15)	C7—C6—H6B	109.2
C8—N1—C7	111.46 (15)	C5—C6—H6B	109.2
C5—O1—H1	107.6 (15)	H6A—C6—H6B	107.9
C2—C1—S1	112.36 (16)	N1—C7—C6	112.78 (15)
C2—C1—H1A	123.8	N1—C7—H7A	109.0
S1—C1—H1A	123.8	C6—C7—H7A	109.0
C1—C2—C3	112.33 (19)	N1—C7—H7B	109.0
C1—C2—H2	123.8	C6—C7—H7B	109.0
C3—C2—H2	123.8	H7A—C7—H7B	107.8
C4—C3—C2	112.95 (17)	N1—C8—H8A	109.5
C4—C3—H3	123.5	N1—C8—H8B	109.5
C2—C3—H3	123.5	H8A—C8—H8B	109.5
C3—C4—C5	130.68 (16)	N1—C8—H8C	109.5
C3—C4—S1	110.14 (14)	H8A—C8—H8C	109.5
C5—C4—S1	119.11 (13)	H8B—C8—H8C	109.5
O1—C5—C4	111.38 (14)	N1—C9—H9A	109.5
O1—C5—C6	111.81 (14)	N1—C9—H9B	109.5
C4—C5—C6	111.74 (14)	H9A—C9—H9B	109.5
O1—C5—H5	107.2	N1—C9—H9C	109.5
C4—C5—H5	107.2	H9A—C9—H9C	109.5
C6—C5—H5	107.2	H9B—C9—H9C	109.5
C7—C6—C5	111.91 (14)
C4—S1—C1—C2	−0.37 (19)	S1—C4—C5—O1	41.05 (19)
S1—C1—C2—C3	0.2 (3)	C3—C4—C5—C6	−16.5 (3)
C1—C2—C3—C4	0.1 (3)	S1—C4—C5—C6	166.90 (12)
C2—C3—C4—C5	−177.21 (18)	O1—C5—C6—C7	−60.5 (2)
C2—C3—C4—S1	−0.4 (2)	C4—C5—C6—C7	173.85 (14)
C1—S1—C4—C3	0.43 (15)	C9—N1—C7—C6	−173.74 (15)
C1—S1—C4—C5	177.67 (15)	C8—N1—C7—C6	64.4 (2)
C3—C4—C5—O1	−142.38 (19)	C5—C6—C7—N1	164.99 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	0.84 (1)	2.02 (1)	2.855 (2)	172 (2)

Symmetry code: (i) −x+1, −y+1, −z+2.