Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005483/wk6013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005483/wk6013Isup2.hkl |
CCDC reference: 242299
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995) and SADABS (Sheldrick, 2002); program(s) used to solve structure: Bruker, SHELXTL; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXS97.
C10H13NO2 | Dx = 1.345 Mg m−3 |
Mr = 179.21 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8192 reflections |
a = 6.6561 (2) Å | θ = 3.5–31.3° |
b = 11.1986 (3) Å | µ = 0.09 mm−1 |
c = 11.8739 (3) Å | T = 183 K |
V = 885.07 (4) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.25 × 0.10 mm |
F(000) = 384 |
Siemens SMART CCD diffractometer | 1854 independent reflections |
Radiation source: fine-focus sealed tube | 1611 reflections with F2 > 2σ(F2) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 32.9°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −10→10 |
Tmin = 0.976, Tmax = 0.991 | k = −17→17 |
15853 measured reflections | l = −17→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0663P)2 + 0.14P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.010 |
1854 reflections | Δρmax = 0.29 e Å−3 |
118 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
Refinement. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped witha Siemens LT-2 A low temperature device. A sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). Exposure time was 20 sec per frame. The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I>10σ(I) after integration of all the frames data using SAINT(Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2002) based on the multiscan method of Blessing (1995). The structure was solved by direct method (Bruker, 1997) and refined by full-matrix least squares on all F2 data using SHELXL97 (Sheldrick, 1997). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.39618 (18) | 0.75038 (11) | 0.11274 (10) | 0.0327 (3) | |
C2 | 0.2399 (3) | 0.66340 (17) | 0.09652 (14) | 0.0327 (3) | |
H2A | 0.2503 | 0.6266 | 0.0209 | 0.039* | |
H2B | 0.1058 | 0.7009 | 0.1041 | 0.039* | |
C3 | 0.2716 (2) | 0.57184 (14) | 0.18662 (14) | 0.0301 (3) | |
H3 | 0.1990 | 0.4992 | 0.1932 | 0.036* | |
C4 | 0.4170 (2) | 0.60737 (13) | 0.25620 (12) | 0.0254 (3) | |
C5 | 0.5189 (3) | 0.54894 (13) | 0.35435 (13) | 0.0285 (3) | |
H5A | 0.4660 | 0.4671 | 0.3650 | 0.034* | |
H5B | 0.4932 | 0.5952 | 0.4239 | 0.034* | |
C6 | 0.7460 (3) | 0.54432 (14) | 0.33031 (15) | 0.0312 (3) | |
H6 | 0.7733 | 0.4854 | 0.2689 | 0.037* | |
C7 | 0.8790 (4) | 0.51595 (19) | 0.4326 (2) | 0.0543 (6) | |
H7A | 0.7971 | 0.4830 | 0.4949 | 0.065* | |
H7B | 0.9836 | 0.4569 | 0.4123 | 0.065* | |
C8 | 0.9739 (3) | 0.63293 (17) | 0.46703 (15) | 0.0397 (4) | |
H8A | 1.1192 | 0.6222 | 0.4816 | 0.048* | |
H8B | 0.9095 | 0.6643 | 0.5361 | 0.048* | |
C9 | 0.9409 (2) | 0.71731 (14) | 0.36935 (13) | 0.0283 (3) | |
N10 | 0.8156 (2) | 0.66315 (12) | 0.29566 (12) | 0.0292 (3) | |
C11 | 0.7250 (2) | 0.72000 (14) | 0.19825 (13) | 0.0277 (3) | |
H11A | 0.7551 | 0.6733 | 0.1295 | 0.033* | |
H11B | 0.7804 | 0.8014 | 0.1886 | 0.033* | |
C12 | 0.4967 (2) | 0.72641 (13) | 0.21673 (12) | 0.0252 (3) | |
H12 | 0.4640 | 0.7898 | 0.2731 | 0.030* | |
O13 | 1.0101 (2) | 0.81856 (11) | 0.35866 (12) | 0.0405 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0304 (5) | 0.0366 (6) | 0.0311 (5) | −0.0048 (5) | −0.0075 (5) | 0.0099 (5) |
C2 | 0.0237 (7) | 0.0409 (8) | 0.0336 (7) | −0.0018 (7) | −0.0036 (6) | 0.0028 (7) |
C3 | 0.0261 (7) | 0.0306 (7) | 0.0336 (7) | −0.0025 (6) | 0.0009 (6) | 0.0003 (6) |
C4 | 0.0258 (6) | 0.0239 (6) | 0.0265 (6) | 0.0000 (5) | 0.0030 (5) | 0.0005 (5) |
C5 | 0.0348 (8) | 0.0218 (6) | 0.0289 (7) | −0.0016 (6) | −0.0001 (6) | 0.0035 (5) |
C6 | 0.0338 (8) | 0.0219 (6) | 0.0380 (8) | −0.0007 (6) | −0.0077 (7) | 0.0038 (6) |
C7 | 0.0543 (12) | 0.0394 (10) | 0.0693 (14) | −0.0067 (9) | −0.0313 (11) | 0.0219 (10) |
C8 | 0.0494 (11) | 0.0383 (9) | 0.0314 (7) | 0.0006 (8) | −0.0111 (8) | 0.0015 (6) |
C9 | 0.0281 (7) | 0.0273 (6) | 0.0296 (7) | 0.0015 (5) | −0.0025 (6) | −0.0031 (6) |
N10 | 0.0290 (6) | 0.0240 (5) | 0.0346 (7) | −0.0020 (5) | −0.0081 (5) | 0.0043 (5) |
C11 | 0.0275 (7) | 0.0284 (7) | 0.0272 (6) | −0.0030 (6) | −0.0028 (6) | 0.0029 (6) |
C12 | 0.0286 (6) | 0.0230 (6) | 0.0239 (6) | 0.0008 (5) | −0.0015 (5) | 0.0014 (5) |
O13 | 0.0444 (7) | 0.0295 (6) | 0.0476 (7) | −0.0074 (5) | −0.0121 (6) | −0.0015 (5) |
O1—C12 | 1.4296 (18) | C6—H6 | 1.0000 |
O1—C2 | 1.438 (2) | C7—C8 | 1.511 (3) |
C2—C3 | 1.497 (2) | C7—H7A | 0.9900 |
C2—H2A | 0.9900 | C7—H7B | 0.9900 |
C2—H2B | 0.9900 | C8—C9 | 1.512 (2) |
C3—C4 | 1.333 (2) | C8—H8A | 0.9900 |
C3—H3 | 0.9500 | C8—H8B | 0.9900 |
C4—C5 | 1.499 (2) | C9—O13 | 1.230 (2) |
C4—C12 | 1.509 (2) | C9—N10 | 1.353 (2) |
C5—C6 | 1.539 (2) | N10—C11 | 1.451 (2) |
C5—H5A | 0.9900 | C11—C12 | 1.538 (2) |
C5—H5B | 0.9900 | C11—H11A | 0.9900 |
C6—N10 | 1.468 (2) | C11—H11B | 0.9900 |
C6—C7 | 1.536 (3) | C12—H12 | 1.0000 |
C12—O1—C2 | 109.09 (11) | C8—C7—H7B | 110.5 |
O1—C2—C3 | 105.43 (13) | C6—C7—H7B | 110.5 |
O1—C2—H2A | 110.7 | H7A—C7—H7B | 108.7 |
C3—C2—H2A | 110.7 | C7—C8—C9 | 105.88 (15) |
O1—C2—H2B | 110.7 | C7—C8—H8A | 110.6 |
C3—C2—H2B | 110.7 | C9—C8—H8A | 110.6 |
H2A—C2—H2B | 108.8 | C7—C8—H8B | 110.6 |
C4—C3—C2 | 109.94 (14) | C9—C8—H8B | 110.6 |
C4—C3—H3 | 125.0 | H8A—C8—H8B | 108.7 |
C2—C3—H3 | 125.0 | O13—C9—N10 | 125.26 (15) |
C3—C4—C5 | 132.86 (14) | O13—C9—C8 | 126.93 (15) |
C3—C4—C12 | 109.04 (13) | N10—C9—C8 | 107.78 (14) |
C5—C4—C12 | 117.89 (13) | C9—N10—C11 | 125.09 (13) |
C4—C5—C6 | 108.37 (13) | C9—N10—C6 | 114.81 (13) |
C4—C5—H5A | 110.0 | C11—N10—C6 | 119.36 (13) |
C6—C5—H5A | 110.0 | N10—C11—C12 | 108.50 (12) |
C4—C5—H5B | 110.0 | N10—C11—H11A | 110.0 |
C6—C5—H5B | 110.0 | C12—C11—H11A | 110.0 |
H5A—C5—H5B | 108.4 | N10—C11—H11B | 110.0 |
N10—C6—C7 | 103.16 (14) | C12—C11—H11B | 110.0 |
N10—C6—C5 | 109.34 (13) | H11A—C11—H11B | 108.4 |
C7—C6—C5 | 115.22 (17) | O1—C12—C4 | 105.64 (12) |
N10—C6—H6 | 109.6 | O1—C12—C11 | 110.37 (12) |
C7—C6—H6 | 109.6 | C4—C12—C11 | 110.53 (13) |
C5—C6—H6 | 109.6 | O1—C12—H12 | 110.1 |
C8—C7—C6 | 106.00 (14) | C4—C12—H12 | 110.1 |
C8—C7—H7A | 110.5 | C11—C12—H12 | 110.1 |
C6—C7—H7A | 110.5 | ||
C12—O1—C2—C3 | −9.32 (17) | C8—C9—N10—C6 | 1.2 (2) |
O1—C2—C3—C4 | 6.16 (19) | C7—C6—N10—C9 | −10.3 (2) |
C2—C3—C4—C5 | −175.19 (16) | C5—C6—N10—C9 | 112.80 (16) |
C2—C3—C4—C12 | −0.70 (18) | C7—C6—N10—C11 | 179.03 (17) |
C3—C4—C5—C6 | 122.46 (19) | C5—C6—N10—C11 | −57.90 (19) |
C12—C4—C5—C6 | −51.64 (18) | C9—N10—C11—C12 | −113.89 (17) |
C4—C5—C6—N10 | 50.02 (17) | C6—N10—C11—C12 | 55.77 (19) |
C4—C5—C6—C7 | 165.62 (14) | C2—O1—C12—C4 | 8.94 (16) |
N10—C6—C7—C8 | 14.8 (2) | C2—O1—C12—C11 | 128.43 (14) |
C5—C6—C7—C8 | −104.2 (2) | C3—C4—C12—O1 | −5.06 (17) |
C6—C7—C8—C9 | −14.6 (2) | C5—C4—C12—O1 | 170.37 (13) |
C7—C8—C9—O13 | −173.1 (2) | C3—C4—C12—C11 | −124.44 (15) |
C7—C8—C9—N10 | 8.7 (2) | C5—C4—C12—C11 | 50.99 (17) |
O13—C9—N10—C11 | −7.0 (3) | N10—C11—C12—O1 | −163.97 (12) |
C8—C9—N10—C11 | 171.29 (15) | N10—C11—C12—C4 | −47.48 (16) |
O13—C9—N10—C6 | −177.09 (17) |