Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019883/ac6057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019883/ac6057Isup2.hkl |
CCDC reference: 225719
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PARST (Nardelli, 1983).
C12H13NO3 | F(000) = 232 |
Mr = 219.23 | Dx = 1.364 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.521 (1) Å | Cell parameters from 2050 reflections |
b = 5.1143 (6) Å | θ = 2.4–28.3° |
c = 12.401 (2) Å | µ = 0.10 mm−1 |
β = 99.098 (2)° | T = 120 K |
V = 533.6 (1) Å3 | Needle, colourless |
Z = 2 | 0.50 × 0.06 × 0.03 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1385 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 1339 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 1.7° |
ω–scan | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −6→6 |
Tmin = 0.843, Tmax = 0.997 | l = −16→16 |
4798 measured reflections |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0819P)2 + 0.0481P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
1385 reflections | Δρmax = 0.40 e Å−3 |
146 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (16) |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.4095 (0.0066) x - 2.9265 (0.0048) y + 2.5256 (0.0123) z = 2.7150 (0.0066) * 0.0054 (0.0017) C11 * -0.0075 (0.0018) C12 * 0.0032 (0.0018) C13 * 0.0033 (0.0019) C14 * -0.0054 (0.0021) C15 * 0.0011 (0.0019) C16 Rms deviation of fitted atoms = 0.0048 7.9709 (0.0023) x - 0.7992 (0.0054) y + 2.0477 (0.0098) z = 2.9788 (0.0029) Angle to previous plane (with approximate e.s.d.) = 26.28 (0.11) * 0.0075 (0.0010) C11 * -0.0023 (0.0018) C17 * -0.0025 (0.0007) O17 * -0.0127 (0.0014) N1 * 0.0100 (0.0010) C1A Rms deviation of fitted atoms = 0.0081 5.7289 (0.0073) x - 3.6501 (0.0042) y - 3.7238 (0.0127) z = 0.5615 (0.0033) Angle to previous plane (with approximate e.s.d.) = 47.30 (0.09) * 0.1757 (0.0014) C1A * -0.1476 (0.0013) C2B * 0.0615 (0.0014) O3G * 0.0539 (0.0014) C5 * -0.1436 (0.0014) C4B 0.1712 (0.0035) O5 - 1.5442 (0.0034) C3G Rms deviation of fitted atoms = 0.1265 |
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. |
x | y | z | Uiso*/Ueq | ||
C11 | 0.2577 (2) | 0.0418 (5) | 0.47163 (17) | 0.0178 (4) | |
C12 | 0.3287 (3) | 0.2528 (6) | 0.53074 (18) | 0.0243 (5) | |
H1 | 0.3930 | 0.3708 | 0.4978 | 0.029* | |
C13 | 0.3057 (3) | 0.2915 (6) | 0.63838 (19) | 0.0307 (6) | |
H2 | 0.3558 | 0.4341 | 0.6793 | 0.037* | |
C14 | 0.2099 (3) | 0.1224 (6) | 0.68542 (18) | 0.0321 (6) | |
H3 | 0.1941 | 0.1490 | 0.7588 | 0.039* | |
C15 | 0.1367 (4) | −0.0862 (6) | 0.6262 (2) | 0.0371 (7) | |
H4 | 0.0699 | −0.2008 | 0.6587 | 0.045* | |
C16 | 0.1609 (3) | −0.1277 (5) | 0.5190 (2) | 0.0294 (5) | |
H5 | 0.1115 | −0.2714 | 0.4785 | 0.035* | |
C17 | 0.2804 (2) | −0.0139 (4) | 0.35645 (16) | 0.0164 (4) | |
O17 | 0.2676 (2) | −0.2382 (3) | 0.31889 (13) | 0.0225 (4) | |
N1 | 0.3150 (2) | 0.1897 (4) | 0.29617 (14) | 0.0167 (4) | |
H6 | 0.3212 | 0.3484 | 0.3239 | 0.020* | |
C1A | 0.3422 (2) | 0.1467 (4) | 0.18473 (15) | 0.0154 (4) | |
H7 | 0.4202 | 0.0006 | 0.1846 | 0.018* | |
C2B | 0.1896 (3) | 0.0788 (5) | 0.10329 (16) | 0.0199 (5) | |
H8 | 0.1774 | −0.1155 | 0.0984 | 0.024* | |
O3G | 0.22233 (18) | 0.1791 (4) | −0.00082 (11) | 0.0237 (4) | |
C3G | 0.0385 (3) | 0.1974 (6) | 0.12968 (19) | 0.0277 (5) | |
H9 | 0.0560 | 0.3830 | 0.1472 | 0.042* | |
H10 | 0.0070 | 0.1066 | 0.1925 | 0.042* | |
H11 | −0.0458 | 0.1797 | 0.0665 | 0.042* | |
C4B | 0.4059 (3) | 0.3862 (5) | 0.13356 (16) | 0.0189 (4) | |
H12 | 0.3660 | 0.5491 | 0.1628 | 0.023* | |
H13 | 0.5235 | 0.3886 | 0.1467 | 0.023* | |
C5 | 0.3422 (3) | 0.3549 (5) | 0.01343 (18) | 0.0211 (5) | |
O5 | 0.3829 (2) | 0.4643 (4) | −0.06277 (13) | 0.0318 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0199 (9) | 0.0187 (10) | 0.0153 (9) | 0.0042 (8) | 0.0047 (7) | 0.0007 (8) |
C12 | 0.0243 (10) | 0.0306 (12) | 0.0183 (9) | −0.0030 (10) | 0.0041 (8) | −0.0040 (10) |
C13 | 0.0308 (11) | 0.0418 (16) | 0.0185 (10) | 0.0030 (11) | 0.0003 (9) | −0.0084 (11) |
C14 | 0.0366 (13) | 0.0460 (17) | 0.0146 (10) | 0.0104 (12) | 0.0068 (9) | 0.0005 (11) |
C15 | 0.0511 (16) | 0.0389 (16) | 0.0264 (12) | −0.0038 (13) | 0.0216 (11) | 0.0046 (12) |
C16 | 0.0397 (13) | 0.0259 (12) | 0.0250 (11) | −0.0045 (12) | 0.0129 (10) | −0.0002 (11) |
C17 | 0.0180 (9) | 0.0156 (10) | 0.0165 (9) | 0.0005 (8) | 0.0053 (7) | −0.0009 (8) |
O17 | 0.0337 (8) | 0.0147 (7) | 0.0211 (8) | −0.0003 (7) | 0.0103 (6) | −0.0019 (7) |
N1 | 0.0260 (8) | 0.0117 (8) | 0.0136 (8) | 0.0002 (7) | 0.0065 (6) | −0.0018 (6) |
C1A | 0.0225 (10) | 0.0119 (9) | 0.0130 (8) | −0.0010 (8) | 0.0070 (7) | −0.0023 (8) |
C2B | 0.0265 (11) | 0.0190 (10) | 0.0148 (9) | −0.0063 (9) | 0.0056 (8) | −0.0001 (8) |
O3G | 0.0297 (8) | 0.0285 (9) | 0.0139 (7) | −0.0050 (8) | 0.0064 (6) | 0.0013 (7) |
C3G | 0.0218 (10) | 0.0373 (14) | 0.0247 (10) | −0.0011 (11) | 0.0056 (8) | 0.0046 (11) |
C4B | 0.0268 (10) | 0.0140 (9) | 0.0174 (9) | −0.0018 (8) | 0.0083 (8) | −0.0013 (8) |
C5 | 0.0257 (10) | 0.0216 (10) | 0.0180 (9) | 0.0018 (9) | 0.0097 (8) | 0.0016 (8) |
O5 | 0.0414 (10) | 0.0354 (11) | 0.0213 (8) | −0.0047 (8) | 0.0136 (7) | 0.0064 (8) |
C11—C12 | 1.388 (3) | N1—H6 | 0.8800 |
C11—C16 | 1.389 (3) | C1A—C4B | 1.519 (3) |
C11—C17 | 1.499 (3) | C1A—C2B | 1.554 (3) |
C12—C13 | 1.394 (3) | C1A—H7 | 1.0000 |
C12—H1 | 0.9500 | C2B—O3G | 1.457 (2) |
C13—C14 | 1.380 (4) | C2B—C3G | 1.505 (3) |
C13—H2 | 0.9500 | C2B—H8 | 1.0000 |
C14—C15 | 1.386 (4) | O3G—C5 | 1.351 (3) |
C14—H3 | 0.9500 | C3G—H9 | 0.9800 |
C15—C16 | 1.393 (3) | C3G—H10 | 0.9800 |
C15—H4 | 0.9500 | C3G—H11 | 0.9800 |
C16—H5 | 0.9500 | C4B—C5 | 1.511 (3) |
C17—O17 | 1.236 (3) | C4B—H12 | 0.9900 |
C17—N1 | 1.342 (3) | C4B—H13 | 0.9900 |
N1—C1A | 1.454 (2) | C5—O5 | 1.196 (3) |
C12—C11—C16 | 120.0 (2) | C4B—C1A—C2B | 103.1 (2) |
C12—C11—C17 | 122.7 (2) | N1—C1A—H7 | 108.7 |
C16—C11—C17 | 117.4 (2) | C4B—C1A—H7 | 108.7 |
C11—C12—C13 | 120.0 (2) | C2B—C1A—H7 | 108.7 |
C11—C12—H1 | 120.0 | O3G—C2B—C3G | 109.9 (2) |
C13—C12—H1 | 120.0 | O3G—C2B—C1A | 103.9 (2) |
C14—C13—C12 | 119.9 (2) | C3G—C2B—C1A | 115.2 (2) |
C14—C13—H2 | 120.1 | O3G—C2B—H8 | 109.2 |
C12—C13—H2 | 120.1 | C3G—C2B—H8 | 109.2 |
C13—C14—C15 | 120.3 (2) | C1A—C2B—H8 | 109.2 |
C13—C14—H3 | 119.8 | C5—O3G—C2B | 111.4 (2) |
C15—C14—H3 | 119.8 | C2B—C3G—H9 | 109.5 |
C14—C15—C16 | 120.0 (2) | C2B—C3G—H10 | 109.5 |
C14—C15—H4 | 120.0 | H9—C3G—H10 | 109.5 |
C16—C15—H4 | 120.0 | C2B—C3G—H11 | 109.5 |
C11—C16—C15 | 119.7 (2) | H9—C3G—H11 | 109.5 |
C11—C16—H5 | 120.1 | H10—C3G—H11 | 109.5 |
C15—C16—H5 | 120.1 | C5—C4B—C1A | 103.3 (2) |
O17—C17—N1 | 121.6 (2) | C5—C4B—H12 | 111.1 |
O17—C17—C11 | 121.2 (2) | C1A—C4B—H12 | 111.1 |
N1—C17—C11 | 117.2 (2) | C5—C4B—H13 | 111.1 |
C17—N1—C1A | 119.6 (2) | C1A—C4B—H13 | 111.1 |
C17—N1—H6 | 120.2 | H12—C4B—H13 | 109.1 |
C1A—N1—H6 | 120.2 | O5—C5—O3G | 121.0 (2) |
N1—C1A—C4B | 113.3 (2) | O5—C5—C4B | 128.8 (2) |
N1—C1A—C2B | 114.1 (2) | O3G—C5—C4B | 110.2 (2) |
C16—C11—C12—C13 | 1.3 (4) | C17—N1—C1A—C4B | −170.66 (18) |
C17—C11—C12—C13 | −178.7 (2) | C17—N1—C1A—C2B | 71.8 (2) |
C11—C12—C13—C14 | −1.1 (4) | N1—C1A—C2B—O3G | 150.75 (17) |
C12—C13—C14—C15 | 0.1 (4) | C4B—C1A—C2B—O3G | 27.4 (2) |
C13—C14—C15—C16 | 0.7 (4) | N1—C1A—C2B—C3G | 30.5 (3) |
C12—C11—C16—C15 | −0.5 (4) | C4B—C1A—C2B—C3G | −92.9 (2) |
C17—C11—C16—C15 | 179.5 (2) | C3G—C2B—O3G—C5 | 105.5 (2) |
C14—C15—C16—C11 | −0.5 (4) | C1A—C2B—O3G—C5 | −18.2 (2) |
C12—C11—C17—O17 | 153.7 (2) | N1—C1A—C4B—C5 | −150.28 (18) |
C16—C11—C17—O17 | −26.3 (3) | C2B—C1A—C4B—C5 | −26.4 (2) |
C12—C11—C17—N1 | −26.4 (3) | C2B—O3G—C5—O5 | −177.8 (2) |
C16—C11—C17—N1 | 153.6 (2) | C2B—O3G—C5—C4B | 1.1 (3) |
O17—C17—N1—C1A | −1.6 (3) | C1A—C4B—C5—O5 | −164.4 (2) |
C11—C17—N1—C1A | 178.53 (18) | C1A—C4B—C5—O3G | 16.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H6···O17i | 0.88 | 2.16 | 2.973 (3) | 153 |
Symmetry code: (i) x, y+1, z. |