Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009819/ob6136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009819/ob6136Isup2.hkl |
CCDC reference: 189896
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: XSHELL (Bruker, 2000); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C10H7NO3 | F(000) = 392 |
Mr = 189.17 | Dx = 1.489 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 753 reflections |
a = 3.864 (1) Å | θ = 2.0–23.3° |
b = 10.691 (3) Å | µ = 0.11 mm−1 |
c = 20.461 (5) Å | T = 168 K |
β = 93.036 (5)° | Needle, orange |
V = 844.0 (4) Å3 | 0.18 × 0.08 × 0.08 mm |
Z = 4 |
Bruker AXS/CCD diffractometer | 1685 independent reflections |
Radiation source: fine-focus sealed tube | 1252 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω and φ scans | θmax = 26.2°, θmin = 2.0° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999) | h = −4→3 |
Tmin = 0.94, Tmax = 0.99 | k = −13→13 |
4735 measured reflections | l = −20→25 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3 |
1685 reflections | (Δ/σ)max = 0.002 |
131 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Experimental. The preliminary unit cell and crystal orientation were determined based on reflections gathered from three sets of 100 frames each, chosen to cover a wide range of reciprocal space. Refined cell parameters were computed after hemishere data collection on the basis of the setting angles of 750 reflections with a resolution limit of 0.9 Angstroms. |
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. Hydrogen atom positions were idealized, and rode on the atoms they were attached to during refinement. These idealized hydrogen atoms had their isotropic temperature factors fixed at 1.2 or 1.5 times the equivalent isotropic U of the C atoms for which they were bonded. The H1 hydrogen was the exception in that it was located by difference fourier maps. H1 had its atom positions and isotropic temperature factor refined. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.9576 (4) | 0.79013 (12) | 0.89665 (6) | 0.0278 (3) | |
O1 | 1.0150 (4) | 0.85985 (13) | 0.62777 (6) | 0.0407 (4) | |
O2 | 1.1984 (4) | 0.59224 (11) | 0.90592 (6) | 0.0447 (4) | |
O3 | 0.7053 (3) | 0.97718 (11) | 0.92632 (6) | 0.0413 (4) | |
C1 | 0.9769 (4) | 0.80945 (14) | 0.82757 (8) | 0.0261 (4) | |
C2 | 1.1316 (4) | 0.91655 (14) | 0.80432 (8) | 0.0274 (4) | |
H2 | 1.2277 | 0.9771 | 0.8340 | 0.033* | |
C3 | 1.1450 (4) | 0.93448 (14) | 0.73764 (8) | 0.0279 (4) | |
H3 | 1.2494 | 1.0079 | 0.7214 | 0.033* | |
C4 | 1.0065 (4) | 0.84577 (14) | 0.69429 (8) | 0.0280 (4) | |
C5 | 0.8548 (4) | 0.73834 (15) | 0.71754 (8) | 0.0292 (4) | |
H5 | 0.7636 | 0.6769 | 0.6878 | 0.035* | |
C6 | 0.8370 (4) | 0.72122 (14) | 0.78416 (8) | 0.0283 (4) | |
H6 | 0.7284 | 0.6486 | 0.8003 | 0.034* | |
C7 | 1.0593 (5) | 0.68185 (16) | 0.92998 (8) | 0.0323 (4) | |
C8 | 0.9693 (5) | 0.69943 (17) | 0.99896 (8) | 0.0362 (4) | |
H8 | 1.0083 | 0.6401 | 1.0331 | 0.043* | |
C9 | 0.8264 (5) | 0.81044 (17) | 1.00529 (8) | 0.0354 (4) | |
H9 | 0.7455 | 0.8441 | 1.0446 | 0.042* | |
C10 | 0.8131 (4) | 0.87416 (16) | 0.94066 (8) | 0.0310 (4) | |
H1 | 1.110 (6) | 0.932 (2) | 0.6196 (11) | 0.060 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0329 (8) | 0.0254 (7) | 0.0256 (8) | 0.0023 (6) | 0.0056 (6) | −0.0005 (5) |
O1 | 0.0550 (9) | 0.0392 (8) | 0.0281 (7) | −0.0096 (6) | 0.0058 (6) | 0.0014 (6) |
O2 | 0.0641 (9) | 0.0326 (7) | 0.0382 (8) | 0.0133 (6) | 0.0101 (6) | 0.0005 (6) |
O3 | 0.0481 (8) | 0.0353 (7) | 0.0404 (8) | 0.0097 (6) | 0.0015 (6) | −0.0081 (6) |
C1 | 0.0260 (9) | 0.0251 (8) | 0.0275 (9) | 0.0038 (7) | 0.0037 (7) | 0.0002 (7) |
C2 | 0.0273 (9) | 0.0236 (8) | 0.0312 (9) | 0.0018 (7) | 0.0001 (7) | −0.0044 (7) |
C3 | 0.0271 (9) | 0.0235 (8) | 0.0332 (9) | −0.0003 (7) | 0.0030 (7) | 0.0045 (7) |
C4 | 0.0281 (9) | 0.0310 (9) | 0.0251 (9) | 0.0032 (7) | 0.0030 (7) | 0.0000 (7) |
C5 | 0.0293 (9) | 0.0273 (8) | 0.0307 (9) | −0.0018 (7) | 0.0009 (7) | −0.0051 (7) |
C6 | 0.0277 (9) | 0.0232 (8) | 0.0344 (10) | −0.0012 (7) | 0.0052 (7) | 0.0002 (7) |
C7 | 0.0353 (10) | 0.0299 (9) | 0.0317 (10) | −0.0013 (8) | 0.0030 (7) | −0.0008 (7) |
C8 | 0.0430 (11) | 0.0395 (10) | 0.0263 (10) | −0.0029 (8) | 0.0046 (8) | 0.0043 (8) |
C9 | 0.0369 (10) | 0.0409 (10) | 0.0285 (10) | −0.0018 (8) | 0.0050 (7) | −0.0051 (8) |
C10 | 0.0273 (9) | 0.0327 (9) | 0.0331 (10) | −0.0008 (7) | 0.0027 (7) | −0.0079 (7) |
N1—C7 | 1.390 (2) | C3—C4 | 1.386 (2) |
N1—C10 | 1.408 (2) | C3—H3 | 0.9500 |
N1—C1 | 1.434 (2) | C4—C5 | 1.385 (2) |
O1—C4 | 1.371 (2) | C5—C6 | 1.381 (2) |
O1—H1 | 0.87 (2) | C5—H5 | 0.9500 |
O2—C7 | 1.215 (2) | C6—H6 | 0.9500 |
O3—C10 | 1.208 (2) | C7—C8 | 1.483 (2) |
C1—C6 | 1.386 (2) | C8—C9 | 1.318 (2) |
C1—C2 | 1.387 (2) | C8—H8 | 0.9500 |
C2—C3 | 1.381 (2) | C9—C10 | 1.486 (2) |
C2—H2 | 0.9500 | C9—H9 | 0.9500 |
C7—N1—C10 | 109.22 (14) | C6—C5—H5 | 120.2 |
C7—N1—C1 | 125.12 (13) | C4—C5—H5 | 120.2 |
C10—N1—C1 | 125.55 (13) | C5—C6—C1 | 120.30 (15) |
C4—O1—H1 | 108.7 (14) | C5—C6—H6 | 119.9 |
C6—C1—C2 | 120.17 (15) | C1—C6—H6 | 119.9 |
C6—C1—N1 | 119.66 (14) | O2—C7—N1 | 125.29 (16) |
C2—C1—N1 | 120.17 (14) | O2—C7—C8 | 128.05 (16) |
C3—C2—C1 | 119.51 (15) | N1—C7—C8 | 106.66 (14) |
C3—C2—H2 | 120.2 | C9—C8—C7 | 109.16 (16) |
C1—C2—H2 | 120.2 | C9—C8—H8 | 125.4 |
C2—C3—C4 | 120.24 (15) | C7—C8—H8 | 125.4 |
C2—C3—H3 | 119.9 | C8—C9—C10 | 108.67 (15) |
C4—C3—H3 | 119.9 | C8—C9—H9 | 125.7 |
O1—C4—C5 | 117.69 (15) | C10—C9—H9 | 125.7 |
O1—C4—C3 | 122.09 (15) | O3—C10—N1 | 124.72 (16) |
C5—C4—C3 | 120.22 (15) | O3—C10—C9 | 128.99 (15) |
C6—C5—C4 | 119.55 (15) | N1—C10—C9 | 106.29 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.87 (2) | 1.95 (2) | 2.820 (2) | 175.17 (15) |
Symmetry code: (i) −x+5/2, y+1/2, −z+3/2. |