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The molecule of the title compound, C8H7ClO3, is almost planar, and there are intramolecular O—H...O, C—H...O and C—H...Cl interactions. The mol­ecules are connected by O—H...O and C—H...O interactions, forming two-dimensional networks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022372/ob6302sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022372/ob6302Isup2.hkl
Contains datablock I

CCDC reference: 226977

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.098
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. Cl = 3.28 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C8H7ClO3F(000) = 384
Mr = 186.59Dx = 1.590 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7841 reflections
a = 6.4910 (5) Åθ = 3.5–27.3°
b = 14.2605 (13) ŵ = 0.45 mm1
c = 8.5148 (9) ÅT = 293 K
β = 98.457 (3)°Prism, colorless
V = 779.60 (12) Å30.26 × 0.22 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1391 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.026
ω scansθmax = 27.3°, θmin = 2.8°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.888, Tmax = 0.923k = 1818
3309 measured reflectionsl = 1010
1755 independent reflections
Refinement top
Refinement on F2All H-atom parameters refined
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0509P)2 + 0.1956P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.036(Δ/σ)max < 0.001
wR(F2) = 0.098Δρmax = 0.28 e Å3
S = 1.01Δρmin = 0.23 e Å3
1755 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
138 parametersExtinction coefficient: 0.0081 (19)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.45643 (8)0.09990 (3)0.08475 (6)0.04703 (18)
O10.0221 (2)0.35347 (8)0.27022 (16)0.0426 (3)
O20.1146 (2)0.17317 (9)0.22546 (18)0.0458 (4)
O30.8072 (2)0.32254 (10)0.09200 (17)0.0508 (4)
C10.5252 (3)0.28639 (12)0.0432 (2)0.0333 (4)
C20.4010 (3)0.21799 (11)0.10152 (19)0.0315 (4)
C30.2322 (3)0.24144 (11)0.17545 (19)0.0323 (4)
C40.1883 (3)0.33706 (11)0.1944 (2)0.0331 (4)
C50.3100 (3)0.40532 (12)0.1387 (2)0.0408 (4)
C60.4749 (3)0.37954 (13)0.0640 (2)0.0408 (4)
C70.7016 (3)0.26397 (14)0.0393 (2)0.0418 (4)
C80.0375 (4)0.44944 (16)0.2855 (3)0.0542 (6)
H20.036 (5)0.1932 (19)0.277 (3)0.077 (9)*
H50.276 (3)0.4717 (15)0.153 (2)0.052 (6)*
H60.551 (3)0.4274 (14)0.028 (2)0.043 (5)*
H70.737 (4)0.2011 (17)0.058 (3)0.063 (7)*
H8A0.067 (5)0.4799 (19)0.182 (3)0.082 (9)*
H8B0.162 (4)0.4465 (17)0.336 (3)0.063 (7)*
H8C0.066 (4)0.4835 (18)0.349 (3)0.074 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0513 (3)0.0316 (2)0.0625 (3)0.00517 (19)0.0229 (2)0.00370 (19)
C10.0299 (8)0.0374 (9)0.0341 (9)0.0003 (7)0.0098 (7)0.0002 (7)
C20.0329 (9)0.0294 (8)0.0334 (8)0.0018 (6)0.0088 (7)0.0021 (6)
C30.0334 (9)0.0311 (8)0.0341 (8)0.0014 (6)0.0105 (7)0.0011 (6)
C40.0321 (8)0.0344 (8)0.0345 (9)0.0020 (7)0.0107 (7)0.0031 (7)
C50.0444 (10)0.0300 (9)0.0510 (11)0.0002 (8)0.0172 (8)0.0023 (7)
C60.0407 (10)0.0349 (9)0.0504 (11)0.0044 (8)0.0186 (8)0.0026 (7)
C70.0376 (10)0.0454 (10)0.0454 (10)0.0011 (8)0.0160 (8)0.0022 (8)
C80.0498 (12)0.0439 (11)0.0735 (16)0.0095 (10)0.0243 (12)0.0115 (11)
O10.0406 (7)0.0394 (7)0.0528 (8)0.0053 (6)0.0238 (6)0.0027 (6)
O20.0463 (8)0.0346 (7)0.0634 (9)0.0036 (6)0.0313 (7)0.0014 (6)
O30.0414 (8)0.0579 (8)0.0584 (9)0.0033 (6)0.0255 (6)0.0010 (7)
Geometric parameters (Å, º) top
Cl—C21.7322 (16)C7—H70.94 (2)
C1—C71.464 (2)C8—H8A0.98 (3)
C2—C31.383 (2)C8—H8B0.97 (3)
C2—C11.402 (2)C8—H8C0.93 (3)
C3—C41.407 (2)C8—O11.433 (2)
C4—C51.381 (2)O1—C41.357 (2)
C5—H50.98 (2)O2—C31.344 (2)
C6—C51.373 (2)O2—H20.77 (3)
C6—C11.385 (2)O3—C71.208 (2)
C6—H60.92 (2)
C1—C2—Cl120.67 (13)C6—C1—C7119.09 (16)
C1—C6—H6121.3 (13)C6—C5—H5121.1 (13)
C1—C7—H7121.0 (15)O1—C4—C5125.24 (15)
C2—C1—C7123.30 (16)O1—C4—C3114.20 (14)
C2—C3—C4118.27 (15)O1—C8—H8C111.6 (16)
C3—C2—C1121.90 (15)O1—C8—H8A111.2 (16)
C3—C2—Cl117.42 (13)O1—C8—H8B104.6 (15)
C3—O2—H2111 (2)O2—C3—C2119.60 (15)
C4—C5—H5119.2 (13)O2—C3—C4122.13 (15)
C4—O1—C8116.88 (15)O3—C7—C1123.63 (18)
C5—C4—C3120.55 (15)O3—C7—H7115.3 (15)
C5—C6—C1122.01 (16)H8A—C8—H8B111 (2)
C5—C6—H6116.7 (13)H8A—C8—H8C109 (2)
C6—C1—C2117.61 (15)H8B—C8—H8C110 (2)
C6—C5—C4119.64 (16)
Cl—C2—C1—C6178.51 (14)C2—C3—C4—C50.7 (3)
Cl—C2—C1—C72.3 (2)C2—C3—C4—O1179.03 (15)
Cl—C2—C3—C4178.16 (13)C3—C2—C1—C60.9 (3)
Cl—C2—C3—O22.4 (2)C3—C2—C1—C7178.31 (17)
O1—C4—C5—C6179.83 (18)C3—C4—C5—C60.1 (3)
O2—C3—C4—O11.5 (3)C5—C6—C1—C20.0 (3)
O2—C3—C4—C5178.67 (17)C5—C6—C1—C7179.21 (18)
C1—C2—C3—O2178.21 (16)C6—C1—C7—O30.4 (3)
C1—C2—C3—C41.2 (3)C8—O1—C4—C53.5 (3)
C1—C6—C5—C40.5 (3)C8—O1—C4—C3176.69 (18)
C2—C1—C7—O3178.81 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.77 (3)2.29 (3)2.6802 (18)113 (2)
O2—H2···O3i0.77 (3)2.00 (3)2.7044 (18)152 (3)
C6—H6···O30.92 (2)2.56 (2)2.814 (2)96.4 (14)
C7—H7···Cl0.94 (2)2.74 (2)3.101 (2)103.3 (17)
C7—H7···O1ii0.94 (2)2.64 (2)3.280 (2)125.6 (18)
C8—H8A···O2iii0.98 (3)2.90 (3)3.229 (3)101.0 (17)
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x+1, y+1/2, z1/2; (iii) x, y+1/2, z+1/2.
 

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