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In the title compound, C
10H
7NO
3, the malamute ring is rotated by 52.75 (5)° with respect to the phenyl ring. There is a weak O—H
O intermolecular hydrogen bond between the hydroxyl group and one of the malamute O atoms, with an O
O distance of 2.820 (2) Å.
Supporting information
CCDC reference: 189896
Key indicators
- Single-crystal X-ray study
- T = 168 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.100
- Data-to-parameter ratio = 12.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
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.
Crystal data top
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 | |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
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