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In the title compound, C10H7NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009819/ob6136sup1.cif
Contains datablocks mar037s, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009819/ob6136Isup2.hkl
Contains datablock I

CCDC reference: 189896

Key indicators

  • Single-crystal X-ray study
  • T = 168 K
  • Mean [sigma](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








Computing details top

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.

(I) top
Crystal data top
C10H7NO3F(000) = 392
Mr = 189.17Dx = 1.489 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 753 reflections
a = 3.864 (1) Åθ = 2.0–23.3°
b = 10.691 (3) ŵ = 0.11 mm1
c = 20.461 (5) ÅT = 168 K
β = 93.036 (5)°Needle, orange
V = 844.0 (4) Å30.18 × 0.08 × 0.08 mm
Z = 4
Data collection top
Bruker AXS/CCD
diffractometer
1685 independent reflections
Radiation source: fine-focus sealed tube1252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω and φ scansθmax = 26.2°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1999)
h = 43
Tmin = 0.94, Tmax = 0.99k = 1313
4735 measured reflectionsl = 2025
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H 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 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
N10.9576 (4)0.79013 (12)0.89665 (6)0.0278 (3)
O11.0150 (4)0.85985 (13)0.62777 (6)0.0407 (4)
O21.1984 (4)0.59224 (11)0.90592 (6)0.0447 (4)
O30.7053 (3)0.97718 (11)0.92632 (6)0.0413 (4)
C10.9769 (4)0.80945 (14)0.82757 (8)0.0261 (4)
C21.1316 (4)0.91655 (14)0.80432 (8)0.0274 (4)
H21.22770.97710.83400.033*
C31.1450 (4)0.93448 (14)0.73764 (8)0.0279 (4)
H31.24941.00790.72140.033*
C41.0065 (4)0.84577 (14)0.69429 (8)0.0280 (4)
C50.8548 (4)0.73834 (15)0.71754 (8)0.0292 (4)
H50.76360.67690.68780.035*
C60.8370 (4)0.72122 (14)0.78416 (8)0.0283 (4)
H60.72840.64860.80030.034*
C71.0593 (5)0.68185 (16)0.92998 (8)0.0323 (4)
C80.9693 (5)0.69943 (17)0.99896 (8)0.0362 (4)
H81.00830.64011.03310.043*
C90.8264 (5)0.81044 (17)1.00529 (8)0.0354 (4)
H90.74550.84411.04460.042*
C100.8131 (4)0.87416 (16)0.94066 (8)0.0310 (4)
H11.110 (6)0.932 (2)0.6196 (11)0.060 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0329 (8)0.0254 (7)0.0256 (8)0.0023 (6)0.0056 (6)0.0005 (5)
O10.0550 (9)0.0392 (8)0.0281 (7)0.0096 (6)0.0058 (6)0.0014 (6)
O20.0641 (9)0.0326 (7)0.0382 (8)0.0133 (6)0.0101 (6)0.0005 (6)
O30.0481 (8)0.0353 (7)0.0404 (8)0.0097 (6)0.0015 (6)0.0081 (6)
C10.0260 (9)0.0251 (8)0.0275 (9)0.0038 (7)0.0037 (7)0.0002 (7)
C20.0273 (9)0.0236 (8)0.0312 (9)0.0018 (7)0.0001 (7)0.0044 (7)
C30.0271 (9)0.0235 (8)0.0332 (9)0.0003 (7)0.0030 (7)0.0045 (7)
C40.0281 (9)0.0310 (9)0.0251 (9)0.0032 (7)0.0030 (7)0.0000 (7)
C50.0293 (9)0.0273 (8)0.0307 (9)0.0018 (7)0.0009 (7)0.0051 (7)
C60.0277 (9)0.0232 (8)0.0344 (10)0.0012 (7)0.0052 (7)0.0002 (7)
C70.0353 (10)0.0299 (9)0.0317 (10)0.0013 (8)0.0030 (7)0.0008 (7)
C80.0430 (11)0.0395 (10)0.0263 (10)0.0029 (8)0.0046 (8)0.0043 (8)
C90.0369 (10)0.0409 (10)0.0285 (10)0.0018 (8)0.0050 (7)0.0051 (8)
C100.0273 (9)0.0327 (9)0.0331 (10)0.0008 (7)0.0027 (7)0.0079 (7)
Geometric parameters (Å, º) top
N1—C71.390 (2)C3—C41.386 (2)
N1—C101.408 (2)C3—H30.9500
N1—C11.434 (2)C4—C51.385 (2)
O1—C41.371 (2)C5—C61.381 (2)
O1—H10.87 (2)C5—H50.9500
O2—C71.215 (2)C6—H60.9500
O3—C101.208 (2)C7—C81.483 (2)
C1—C61.386 (2)C8—C91.318 (2)
C1—C21.387 (2)C8—H80.9500
C2—C31.381 (2)C9—C101.486 (2)
C2—H20.9500C9—H90.9500
C7—N1—C10109.22 (14)C6—C5—H5120.2
C7—N1—C1125.12 (13)C4—C5—H5120.2
C10—N1—C1125.55 (13)C5—C6—C1120.30 (15)
C4—O1—H1108.7 (14)C5—C6—H6119.9
C6—C1—C2120.17 (15)C1—C6—H6119.9
C6—C1—N1119.66 (14)O2—C7—N1125.29 (16)
C2—C1—N1120.17 (14)O2—C7—C8128.05 (16)
C3—C2—C1119.51 (15)N1—C7—C8106.66 (14)
C3—C2—H2120.2C9—C8—C7109.16 (16)
C1—C2—H2120.2C9—C8—H8125.4
C2—C3—C4120.24 (15)C7—C8—H8125.4
C2—C3—H3119.9C8—C9—C10108.67 (15)
C4—C3—H3119.9C8—C9—H9125.7
O1—C4—C5117.69 (15)C10—C9—H9125.7
O1—C4—C3122.09 (15)O3—C10—N1124.72 (16)
C5—C4—C3120.22 (15)O3—C10—C9128.99 (15)
C6—C5—C4119.55 (15)N1—C10—C9106.29 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.87 (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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