(2-Amino­ethoxy)­bis(2-thienyl)­boron

In the five-membered ring in the title compound, (2-amino­ethoxy)­bis(2-thienyl)­boron, C₁₀H₁₂BNOS_2, the B atom is four-coordinate with dimensions N-B 1.654 (3), O-B 1.479 (3), and C-B 1.606 (3) and 1.609 (3) Å. An intermolecular hydrogen bond between an amino H atom and the ethoxy O atom links the mol­ecules into infinite chains along the a axis. Only one of the two amino H atoms is involved in hydrogen bonding because there is only the one acceptor atom, the ethoxy O atom, and the molecular geometry precludes formation of a second hydrogen bond by the second amino H atom.

S1. Comment

Examination of the title structure, (I), with PLATON (Spek, 1999) showed that there were no solvent-accessible voids in the crystal lattice.

S2. Experimental

The title compound was prepared according to a published procedure (Coutts & Musgrave, 1970) from 2-aminoethanol and bis(2-thienyl)boronic acid, which was obtained from (BuO)₃B and 2-BrMg-thiophene (m.p. 474–476 K, literature value, 473–475 K).

S3. Refinement

Molecule (I) crystallized in the orthorhombic system; space group Pbca from the systematic absences. H atoms were treated as riding atoms with C—H 0.95–0.99 Å and N—H 0.92 Å.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

2-aminoethoxybis(2-thienyl)boron

Crystal data

C10H12BNOS2	Dx = 1.407 Mg m^−3
Mr = 237.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2562 reflections
a = 10.0818 (3) Å	θ = 2.5–27.4°
b = 16.1220 (7) Å	µ = 0.45 mm^−1
c = 13.7747 (6) Å	T = 150 K
V = 2238.92 (15) Å^3	Plate, colourless
Z = 8	0.20 × 0.15 × 0.05 mm
F(000) = 992

Data collection

KappaCCD diffractometer	2562 independent reflections
Radiation source: fine-focus sealed X-ray tube	1888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
ϕ scans and ω scans with κ offsets	θmax = 27.4°, θmin = 2.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −12→12
Tmin = 0.916, Tmax = 0.978	k = −20→20
15841 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.4651P] where P = (Fo^2 + 2Fc^2)/3
2562 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

Experimental. Kappa CCD diffractometer using the following programs. Collect: Data collection software (Hooft, 1998) [Hooft, R. (1998). Nonius BV, Delft, The Netherlands] is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski & Minor, 1997) and indexing and data collection software package and a scaling package, SCALEPACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package (Blessing, 1995, 1997). High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. Low temperature data is collected using an Oxford Cryosystems cryostream (Cosier & Glazer, 1986) [Cosier, J. & Glazer, A·M. (1986). J. Appl. Cryst. 19, 105–107].

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
B1	0.2005 (2)	0.77317 (16)	0.78854 (17)	0.0166 (5)
O1	0.09766 (13)	0.82259 (9)	0.73835 (10)	0.0182 (4)
C2	0.1625 (2)	0.88239 (14)	0.67879 (17)	0.0207 (5)
C3	0.2743 (2)	0.83492 (15)	0.63053 (17)	0.0238 (5)
N4	0.32380 (16)	0.77975 (11)	0.70973 (12)	0.0169 (4)
C11	0.15234 (19)	0.67842 (14)	0.79599 (16)	0.0177 (5)
S21	0.21872 (6)	0.60900 (4)	0.87773 (4)	0.0262 (2)
C31	0.1280 (2)	0.52804 (14)	0.83476 (17)	0.0251 (5)
C41	0.0481 (2)	0.55123 (15)	0.76071 (16)	0.0236 (5)
C51	0.0590 (2)	0.63764 (13)	0.73645 (15)	0.0149 (4)
C12	0.2500 (2)	0.81494 (14)	0.88827 (15)	0.0177 (5)
S22	0.14147 (5)	0.87648 (4)	0.95348 (4)	0.0289 (2)
C32	0.2563 (2)	0.89848 (16)	1.04121 (16)	0.0285 (6)
C42	0.3727 (2)	0.86063 (15)	1.02297 (16)	0.0245 (5)
C52	0.3689 (2)	0.81230 (14)	0.93712 (16)	0.0194 (5)
H2A	0.1977	0.9286	0.7185	0.025*
H2B	0.1007	0.9052	0.6297	0.025*
H3A	0.2413	0.8021	0.5748	0.029*
H3B	0.3448	0.8730	0.6078	0.029*
H4A	0.3979	0.8021	0.7385	0.020*
H4B	0.3450	0.7282	0.6857	0.020*
H31	0.1328	0.4732	0.8597	0.030*
H41	−0.0095	0.5140	0.7279	0.028*
H51	0.0094	0.6640	0.6866	0.018*
H32	0.2400	0.9330	1.0958	0.034*
H42	0.4488	0.8658	1.0632	0.029*
H52	0.4425	0.7807	0.9151	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0122 (11)	0.0200 (13)	0.0175 (12)	−0.0004 (9)	0.0008 (9)	0.0010 (10)
O1	0.0127 (7)	0.0204 (8)	0.0216 (8)	−0.0010 (6)	0.0001 (6)	0.0028 (6)
C2	0.0177 (10)	0.0179 (12)	0.0265 (12)	−0.0013 (9)	−0.0015 (9)	0.0043 (10)
C3	0.0202 (11)	0.0289 (13)	0.0222 (12)	0.0032 (10)	0.0025 (9)	0.0074 (10)
N4	0.0139 (8)	0.0187 (10)	0.0182 (9)	0.0012 (7)	−0.0001 (7)	0.0001 (7)
C11	0.0144 (10)	0.0206 (12)	0.0181 (11)	0.0014 (8)	0.0037 (9)	0.0007 (9)
S21	0.0229 (3)	0.0270 (4)	0.0287 (4)	−0.0004 (2)	−0.0017 (2)	0.0045 (3)
C31	0.0257 (12)	0.0175 (12)	0.0321 (14)	0.0025 (9)	0.0066 (10)	0.0011 (10)
C41	0.0217 (11)	0.0229 (13)	0.0262 (12)	−0.0049 (10)	0.0052 (10)	−0.0046 (10)
C51	0.0156 (10)	0.0127 (11)	0.0163 (10)	−0.0024 (8)	0.0078 (8)	−0.0023 (8)
C12	0.0180 (10)	0.0163 (11)	0.0188 (11)	−0.0026 (8)	0.0012 (9)	0.0012 (9)
S22	0.0204 (3)	0.0370 (4)	0.0294 (4)	0.0007 (2)	0.0032 (2)	−0.0107 (3)
C32	0.0368 (14)	0.0306 (14)	0.0180 (12)	−0.0101 (11)	0.0040 (10)	−0.0071 (10)
C42	0.0259 (12)	0.0277 (13)	0.0199 (12)	−0.0106 (10)	−0.0044 (9)	0.0036 (10)
C52	0.0173 (10)	0.0210 (13)	0.0197 (11)	−0.0031 (9)	0.0019 (9)	0.0031 (9)

Geometric parameters (Å, º)

B1—O1	1.479 (3)	S21—C31	1.700 (2)
B1—C11	1.606 (3)	C31—C41	1.352 (3)
B1—C12	1.609 (3)	C41—C51	1.437 (3)
B1—N4	1.654 (3)	C12—C52	1.375 (3)
O1—C2	1.425 (2)	C12—S22	1.729 (2)
C2—C3	1.516 (3)	S22—C32	1.711 (2)
C3—N4	1.493 (3)	C32—C42	1.346 (3)
C11—C51	1.411 (3)	C42—C52	1.417 (3)
C11—S21	1.723 (2)
O1—B1—C11	109.30 (16)	B1—C11—S21	122.84 (15)
O1—B1—C12	113.03 (18)	C31—S21—C11	93.56 (11)
C11—B1—C12	115.93 (19)	C41—C31—S21	111.76 (18)
O1—B1—N4	100.69 (16)	C31—C41—C51	113.5 (2)
C11—B1—N4	109.27 (17)	C11—C51—C41	111.55 (19)
C12—B1—N4	107.46 (16)	C52—C12—B1	132.5 (2)
C2—O1—B1	108.20 (15)	C52—C12—S22	108.38 (16)
O1—C2—C3	104.59 (17)	B1—C12—S22	119.15 (15)
N4—C3—C2	103.24 (17)	C32—S22—C12	93.30 (11)
C3—N4—B1	105.45 (15)	C42—C32—S22	111.35 (18)
C51—C11—B1	127.42 (19)	C32—C42—C52	112.4 (2)
C51—C11—S21	109.65 (16)	C12—C52—C42	114.5 (2)
C11—B1—O1—C2	−142.97 (17)	S21—C31—C41—C51	0.0 (2)
C12—B1—O1—C2	86.3 (2)	B1—C11—C51—C41	175.93 (19)
N4—B1—O1—C2	−28.0 (2)	S21—C11—C51—C41	−0.6 (2)
B1—O1—C2—C3	43.5 (2)	C31—C41—C51—C11	0.4 (3)
O1—C2—C3—N4	−39.4 (2)	O1—B1—C12—C52	−150.7 (2)
C2—C3—N4—B1	21.1 (2)	C11—B1—C12—C52	82.0 (3)
O1—B1—N4—C3	2.8 (2)	N4—B1—C12—C52	−40.5 (3)
C11—B1—N4—C3	117.79 (19)	O1—B1—C12—S22	29.4 (2)
C12—B1—N4—C3	−115.65 (19)	C11—B1—C12—S22	−97.9 (2)
O1—B1—C11—C51	23.2 (3)	N4—B1—C12—S22	139.55 (15)
C12—B1—C11—C51	152.31 (19)	C52—C12—S22—C32	1.18 (18)
N4—B1—C11—C51	−86.1 (2)	B1—C12—S22—C32	−178.89 (18)
O1—B1—C11—S21	−160.72 (14)	C12—S22—C32—C42	−0.35 (19)
C12—B1—C11—S21	−31.6 (2)	S22—C32—C42—C52	−0.6 (3)
N4—B1—C11—S21	90.0 (2)	B1—C12—C52—C42	178.3 (2)
C51—C11—S21—C31	0.50 (16)	S22—C12—C52—C42	−1.7 (2)
B1—C11—S21—C31	−176.21 (17)	C32—C42—C52—C12	1.6 (3)
C11—S21—C31—C41	−0.28 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1^i	0.92	2.07	2.935 (2)	157

Symmetry code: (i) x+1/2, y, −z+3/2.