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The asymmetric unit of the title compound, C8H3ClO3, contains two mol­ecules. The molecular packing is controlled by C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001230/dn6115sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001230/dn6115Isup2.hkl
Contains datablock I

CCDC reference: 234892

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.104
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H6 .. O6 = 3.03 Ang.
Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O6 = 3.08 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C16 = 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O1 = 2.80 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O6 = 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O2 = 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O1 = 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O2 = 2.81 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O4 = 2.61 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 2 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 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994_; cell refinement: CAD-4 EXPRESS; data reduction: DATARED (Harms & Wocadlo, 1995); 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
C8H3ClO3Z = 4
Mr = 182.55F(000) = 368
Triclinic, P1Dx = 1.604 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.929 (2) ÅCell parameters from 4173 reflections
b = 7.854 (1) Åθ = 1.5–27.2°
c = 14.262 (2) ŵ = 0.46 mm1
α = 77.69 (1)°T = 293 K
β = 88.09 (1)°Prism, colourless
γ = 85.48 (2)°0.4 × 0.2 × 0.1 mm
V = 755.8 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.015
ω/2θ scansθmax = 27.2°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements)
North et al., 1968
h = 18
Tmin = 0.837, Tmax = 0.955k = 1010
4173 measured reflectionsl = 1818
3336 independent reflections3 standard reflections every 100 reflections
2184 reflections with I > 2σ(I) intensity decay: 0.5%
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.2624P]
where P = (Fo2 + 2Fc2)/3
3336 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
C10.3212 (3)0.2193 (3)0.85605 (15)0.0462 (5)
C20.4936 (3)0.1266 (3)0.84215 (14)0.0469 (5)
C30.6503 (3)0.1204 (3)0.89992 (16)0.0528 (5)
H30.76700.05910.89020.063*
C40.6240 (3)0.2103 (3)0.97325 (16)0.0533 (5)
C50.4491 (3)0.2986 (3)0.98969 (16)0.0553 (5)
H50.43570.35351.04150.066*
C60.2959 (3)0.3059 (3)0.93035 (16)0.0530 (5)
H60.17910.36710.93990.064*
C70.1873 (4)0.2005 (3)0.78186 (16)0.0562 (5)
C80.4676 (4)0.0412 (3)0.76166 (16)0.0597 (6)
C90.2340 (3)0.3788 (2)0.38328 (14)0.0422 (4)
C100.1032 (3)0.3352 (3)0.32357 (14)0.0441 (4)
C110.0642 (3)0.2581 (3)0.35791 (16)0.0518 (5)
H110.15240.22860.31740.062*
C120.0931 (3)0.2275 (3)0.45612 (17)0.0528 (5)
C130.0390 (3)0.2679 (3)0.51685 (16)0.0579 (6)
H130.01520.24270.58270.069*
C140.2058 (3)0.3453 (3)0.48115 (15)0.0533 (5)
H140.29530.37360.52150.064*
C150.3910 (3)0.4619 (3)0.32289 (16)0.0512 (5)
C160.1766 (3)0.3868 (3)0.22439 (16)0.0540 (5)
O10.0252 (3)0.2577 (3)0.76504 (14)0.0765 (5)
O20.2818 (3)0.0922 (2)0.72697 (11)0.0641 (4)
O30.5714 (3)0.0572 (3)0.72757 (14)0.0879 (6)
O40.5314 (2)0.5253 (2)0.34222 (13)0.0731 (5)
O50.3512 (2)0.4620 (2)0.22825 (10)0.0567 (4)
O60.1155 (3)0.3741 (3)0.15003 (12)0.0785 (5)
Cl10.30224 (10)0.13513 (10)0.50506 (6)0.0845 (3)
Cl20.81385 (10)0.21374 (10)1.04831 (5)0.0795 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0473 (11)0.0417 (10)0.0475 (11)0.0075 (9)0.0040 (9)0.0042 (9)
C20.0518 (12)0.0405 (10)0.0449 (11)0.0058 (9)0.0086 (9)0.0021 (8)
C30.0446 (11)0.0497 (12)0.0578 (13)0.0057 (9)0.0070 (9)0.0026 (10)
C40.0542 (13)0.0529 (12)0.0503 (12)0.0210 (10)0.0024 (10)0.0013 (10)
C50.0653 (15)0.0520 (12)0.0511 (12)0.0184 (11)0.0076 (10)0.0122 (10)
C60.0528 (13)0.0477 (12)0.0586 (13)0.0069 (10)0.0097 (10)0.0120 (10)
C70.0587 (14)0.0532 (13)0.0541 (13)0.0092 (11)0.0000 (11)0.0042 (10)
C80.0762 (16)0.0512 (13)0.0489 (12)0.0014 (12)0.0086 (11)0.0069 (10)
C90.0400 (10)0.0396 (10)0.0460 (11)0.0013 (8)0.0027 (8)0.0080 (8)
C100.0401 (10)0.0464 (11)0.0451 (11)0.0019 (8)0.0010 (8)0.0098 (9)
C110.0408 (11)0.0557 (13)0.0608 (13)0.0037 (9)0.0013 (9)0.0162 (10)
C120.0429 (11)0.0456 (11)0.0639 (14)0.0039 (9)0.0117 (10)0.0026 (10)
C130.0614 (14)0.0592 (13)0.0460 (12)0.0116 (11)0.0070 (10)0.0026 (10)
C140.0565 (13)0.0552 (13)0.0475 (12)0.0037 (10)0.0086 (10)0.0112 (10)
C150.0454 (11)0.0486 (12)0.0566 (13)0.0031 (9)0.0060 (9)0.0035 (9)
C160.0465 (12)0.0666 (14)0.0493 (12)0.0016 (10)0.0008 (9)0.0141 (10)
O10.0567 (11)0.0894 (13)0.0811 (12)0.0020 (9)0.0135 (9)0.0121 (10)
O20.0776 (11)0.0635 (10)0.0526 (9)0.0048 (9)0.0064 (8)0.0148 (8)
O30.1097 (16)0.0810 (13)0.0739 (12)0.0203 (12)0.0118 (11)0.0300 (10)
O40.0592 (10)0.0780 (12)0.0802 (12)0.0255 (9)0.0098 (9)0.0039 (9)
O50.0487 (8)0.0681 (10)0.0497 (9)0.0089 (7)0.0043 (6)0.0031 (7)
O60.0704 (11)0.1223 (16)0.0468 (9)0.0112 (11)0.0055 (8)0.0251 (10)
Cl10.0555 (4)0.0787 (5)0.1069 (6)0.0068 (3)0.0290 (4)0.0040 (4)
Cl20.0710 (4)0.0875 (5)0.0768 (4)0.0327 (4)0.0188 (3)0.0020 (3)
Geometric parameters (Å, º) top
C1—C61.376 (3)C9—C101.374 (3)
C1—C21.380 (3)C9—C141.374 (3)
C1—C71.468 (3)C9—C151.470 (3)
C2—C31.376 (3)C10—C111.378 (3)
C2—C81.470 (3)C10—C161.471 (3)
C3—C41.382 (3)C11—C121.380 (3)
C3—H30.9300C11—H110.9300
C4—C51.387 (3)C12—C131.380 (3)
C4—Cl21.729 (2)C12—Cl11.731 (2)
C5—C61.370 (3)C13—C141.380 (3)
C5—H50.9300C13—H130.9300
C6—H60.9300C14—H140.9300
C7—O11.189 (3)C15—O41.193 (3)
C7—O21.388 (3)C15—O51.386 (3)
C8—O31.183 (3)C16—O61.181 (3)
C8—O21.393 (3)C16—O51.395 (3)
C6—C1—C2121.4 (2)C10—C9—C15107.64 (18)
C6—C1—C7130.8 (2)C14—C9—C15130.80 (19)
C2—C1—C7107.75 (19)C9—C10—C11122.18 (19)
C3—C2—C1121.8 (2)C9—C10—C16107.88 (18)
C3—C2—C8130.6 (2)C11—C10—C16129.9 (2)
C1—C2—C8107.5 (2)C10—C11—C12115.9 (2)
C2—C3—C4116.1 (2)C10—C11—H11122.0
C2—C3—H3121.9C12—C11—H11122.0
C4—C3—H3121.9C13—C12—C11122.3 (2)
C3—C4—C5122.3 (2)C13—C12—Cl1118.71 (18)
C3—C4—Cl2119.58 (19)C11—C12—Cl1118.95 (18)
C5—C4—Cl2118.08 (18)C12—C13—C14120.9 (2)
C6—C5—C4120.6 (2)C12—C13—H13119.5
C6—C5—H5119.7C14—C13—H13119.5
C4—C5—H5119.7C9—C14—C13117.1 (2)
C5—C6—C1117.6 (2)C9—C14—H14121.5
C5—C6—H6121.2C13—C14—H14121.5
C1—C6—H6121.2O4—C15—O5120.5 (2)
O1—C7—O2120.5 (2)O4—C15—C9131.7 (2)
O1—C7—C1131.8 (2)O5—C15—C9107.71 (17)
O2—C7—C1107.7 (2)O6—C16—O5120.5 (2)
O3—C8—O2120.8 (2)O6—C16—C10132.2 (2)
O3—C8—C2131.6 (3)O5—C16—C10107.27 (18)
O2—C8—C2107.58 (19)C7—O2—C8109.44 (18)
C10—C9—C14121.56 (19)C15—O5—C16109.48 (16)
C6—C1—C2—C31.9 (3)C9—C10—C11—C120.1 (3)
C7—C1—C2—C3179.21 (18)C16—C10—C11—C12179.3 (2)
C6—C1—C2—C8176.22 (19)C10—C11—C12—C131.3 (3)
C7—C1—C2—C82.6 (2)C10—C11—C12—Cl1178.70 (15)
C1—C2—C3—C40.8 (3)C11—C12—C13—C141.4 (3)
C8—C2—C3—C4176.9 (2)Cl1—C12—C13—C14178.54 (17)
C2—C3—C4—C51.5 (3)C10—C9—C14—C130.8 (3)
C2—C3—C4—Cl2178.79 (15)C15—C9—C14—C13178.4 (2)
C3—C4—C5—C62.7 (3)C12—C13—C14—C90.3 (3)
Cl2—C4—C5—C6177.56 (16)C10—C9—C15—O4177.3 (2)
C4—C5—C6—C11.5 (3)C14—C9—C15—O42.0 (4)
C2—C1—C6—C50.7 (3)C10—C9—C15—O51.3 (2)
C7—C1—C6—C5179.3 (2)C14—C9—C15—O5179.3 (2)
C6—C1—C7—O12.0 (4)C9—C10—C16—O6179.2 (3)
C2—C1—C7—O1179.3 (2)C11—C10—C16—O61.4 (4)
C6—C1—C7—O2176.9 (2)C9—C10—C16—O50.4 (2)
C2—C1—C7—O21.8 (2)C11—C10—C16—O5179.0 (2)
C3—C2—C8—O32.1 (4)O1—C7—O2—C8179.2 (2)
C1—C2—C8—O3175.8 (3)C1—C7—O2—C80.1 (2)
C3—C2—C8—O2179.4 (2)O3—C8—O2—C7177.1 (2)
C1—C2—C8—O22.6 (2)C2—C8—O2—C71.5 (2)
C14—C9—C10—C111.0 (3)O4—C15—O5—C16177.8 (2)
C15—C9—C10—C11178.46 (19)C9—C15—O5—C161.1 (2)
C14—C9—C10—C16179.56 (19)O6—C16—O5—C15179.9 (2)
C15—C9—C10—C161.0 (2)C10—C16—O5—C150.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.803.292 (3)114
C6—H6···O6ii0.933.033.466 (3)111
C6—H6···O6iii0.932.893.690 (3)145
C11—H11···O2iv0.932.943.675 (3)137
C13—H13···O10.932.633.522 (3)161
C13—H13···O20.932.813.453 (3)127
C14—H14···O4v0.932.613.519 (3)166
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x, y, z+1; (v) x+1, y+1, z+1.
 

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