Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000482/qb0168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000482/qb0168Isup2.hkl |
CCDC reference: 142942
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).
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.
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).
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) Å3 | Plate, colourless |
Z = 8 | 0.20 × 0.15 × 0.05 mm |
F(000) = 992 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0636P)2 + 0.4651P] where P = (Fo2 + 2Fc2)/3 |
2562 reflections | (Δ/σ)max = 0.001 |
136 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C10H12BNOS2 | V = 2238.92 (15) Å3 |
Mr = 237.14 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.0818 (3) Å | µ = 0.45 mm−1 |
b = 16.1220 (7) Å | T = 150 K |
c = 13.7747 (6) Å | 0.20 × 0.15 × 0.05 mm |
KappaCCD diffractometer | 2562 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | 1888 reflections with I > 2σ(I) |
Tmin = 0.916, Tmax = 0.978 | Rint = 0.084 |
15841 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.55 e Å−3 |
2562 reflections | Δρmin = −0.47 e Å−3 |
136 parameters |
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]. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1i | 0.92 | 2.07 | 2.935 (2) | 157 |
Symmetry code: (i) x+1/2, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C10H12BNOS2 |
Mr | 237.14 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 150 |
a, b, c (Å) | 10.0818 (3), 16.1220 (7), 13.7747 (6) |
V (Å3) | 2238.92 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.45 |
Crystal size (mm) | 0.20 × 0.15 × 0.05 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995, 1997) |
Tmin, Tmax | 0.916, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15841, 2562, 1888 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.122, 1.06 |
No. of reflections | 2562 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.47 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Examination of the title structure, (I), with PLATON (Spek, 1999) showed that there were no solvent-accessible voids in the crystal lattice.