Buy article online - an online subscription or single-article purchase is required to access this article.
The asymmetric unit of the title compound, C
8H
3ClO
3, contains two molecules. The molecular packing is controlled by C—H
O hydrogen bonding.
Supporting information
CCDC reference: 234892
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
C8H3ClO3 | Z = 4 |
Mr = 182.55 | F(000) = 368 |
Triclinic, P1 | Dx = 1.604 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.929 (2) Å | Cell parameters from 4173 reflections |
b = 7.854 (1) Å | θ = 1.5–27.2° |
c = 14.262 (2) Å | µ = 0.46 mm−1 |
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 scans | θmax = 27.2°, θmin = 1.5° |
Absorption correction: empirical (using intensity measurements) North et al., 1968 | h = −1→8 |
Tmin = 0.837, Tmax = 0.955 | k = −10→10 |
4173 measured reflections | l = −18→18 |
3336 independent reflections | 3 standard reflections every 100 reflections |
2184 reflections with I > 2σ(I) | intensity decay: 0.5% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3212 (3) | 0.2193 (3) | 0.85605 (15) | 0.0462 (5) | |
C2 | 0.4936 (3) | 0.1266 (3) | 0.84215 (14) | 0.0469 (5) | |
C3 | 0.6503 (3) | 0.1204 (3) | 0.89992 (16) | 0.0528 (5) | |
H3 | 0.7670 | 0.0591 | 0.8902 | 0.063* | |
C4 | 0.6240 (3) | 0.2103 (3) | 0.97325 (16) | 0.0533 (5) | |
C5 | 0.4491 (3) | 0.2986 (3) | 0.98969 (16) | 0.0553 (5) | |
H5 | 0.4357 | 0.3535 | 1.0415 | 0.066* | |
C6 | 0.2959 (3) | 0.3059 (3) | 0.93035 (16) | 0.0530 (5) | |
H6 | 0.1791 | 0.3671 | 0.9399 | 0.064* | |
C7 | 0.1873 (4) | 0.2005 (3) | 0.78186 (16) | 0.0562 (5) | |
C8 | 0.4676 (4) | 0.0412 (3) | 0.76166 (16) | 0.0597 (6) | |
C9 | 0.2340 (3) | 0.3788 (2) | 0.38328 (14) | 0.0422 (4) | |
C10 | 0.1032 (3) | 0.3352 (3) | 0.32357 (14) | 0.0441 (4) | |
C11 | −0.0642 (3) | 0.2581 (3) | 0.35791 (16) | 0.0518 (5) | |
H11 | −0.1524 | 0.2286 | 0.3174 | 0.062* | |
C12 | −0.0931 (3) | 0.2275 (3) | 0.45612 (17) | 0.0528 (5) | |
C13 | 0.0390 (3) | 0.2679 (3) | 0.51685 (16) | 0.0579 (6) | |
H13 | 0.0152 | 0.2427 | 0.5827 | 0.069* | |
C14 | 0.2058 (3) | 0.3453 (3) | 0.48115 (15) | 0.0533 (5) | |
H14 | 0.2953 | 0.3736 | 0.5215 | 0.064* | |
C15 | 0.3910 (3) | 0.4619 (3) | 0.32289 (16) | 0.0512 (5) | |
C16 | 0.1766 (3) | 0.3868 (3) | 0.22439 (16) | 0.0540 (5) | |
O1 | 0.0252 (3) | 0.2577 (3) | 0.76504 (14) | 0.0765 (5) | |
O2 | 0.2818 (3) | 0.0922 (2) | 0.72697 (11) | 0.0641 (4) | |
O3 | 0.5714 (3) | −0.0572 (3) | 0.72757 (14) | 0.0879 (6) | |
O4 | 0.5314 (2) | 0.5253 (2) | 0.34222 (13) | 0.0731 (5) | |
O5 | 0.3512 (2) | 0.4620 (2) | 0.22825 (10) | 0.0567 (4) | |
O6 | 0.1155 (3) | 0.3741 (3) | 0.15003 (12) | 0.0785 (5) | |
Cl1 | −0.30224 (10) | 0.13513 (10) | 0.50506 (6) | 0.0845 (3) | |
Cl2 | 0.81385 (10) | 0.21374 (10) | 1.04831 (5) | 0.0795 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0473 (11) | 0.0417 (10) | 0.0475 (11) | −0.0075 (9) | 0.0040 (9) | −0.0042 (9) |
C2 | 0.0518 (12) | 0.0405 (10) | 0.0449 (11) | −0.0058 (9) | 0.0086 (9) | −0.0021 (8) |
C3 | 0.0446 (11) | 0.0497 (12) | 0.0578 (13) | −0.0057 (9) | 0.0070 (9) | 0.0026 (10) |
C4 | 0.0542 (13) | 0.0529 (12) | 0.0503 (12) | −0.0210 (10) | −0.0024 (10) | 0.0013 (10) |
C5 | 0.0653 (15) | 0.0520 (12) | 0.0511 (12) | −0.0184 (11) | 0.0076 (10) | −0.0122 (10) |
C6 | 0.0528 (13) | 0.0477 (12) | 0.0586 (13) | −0.0069 (10) | 0.0097 (10) | −0.0120 (10) |
C7 | 0.0587 (14) | 0.0532 (13) | 0.0541 (13) | −0.0092 (11) | 0.0000 (11) | −0.0042 (10) |
C8 | 0.0762 (16) | 0.0512 (13) | 0.0489 (12) | −0.0014 (12) | 0.0086 (11) | −0.0069 (10) |
C9 | 0.0400 (10) | 0.0396 (10) | 0.0460 (11) | 0.0013 (8) | −0.0027 (8) | −0.0080 (8) |
C10 | 0.0401 (10) | 0.0464 (11) | 0.0451 (11) | 0.0019 (8) | −0.0010 (8) | −0.0098 (9) |
C11 | 0.0408 (11) | 0.0557 (13) | 0.0608 (13) | −0.0037 (9) | −0.0013 (9) | −0.0162 (10) |
C12 | 0.0429 (11) | 0.0456 (11) | 0.0639 (14) | 0.0039 (9) | 0.0117 (10) | −0.0026 (10) |
C13 | 0.0614 (14) | 0.0592 (13) | 0.0460 (12) | 0.0116 (11) | 0.0070 (10) | −0.0026 (10) |
C14 | 0.0565 (13) | 0.0552 (13) | 0.0475 (12) | 0.0037 (10) | −0.0086 (10) | −0.0112 (10) |
C15 | 0.0454 (11) | 0.0486 (12) | 0.0566 (13) | −0.0031 (9) | −0.0060 (9) | −0.0035 (9) |
C16 | 0.0465 (12) | 0.0666 (14) | 0.0493 (12) | −0.0016 (10) | −0.0008 (9) | −0.0141 (10) |
O1 | 0.0567 (11) | 0.0894 (13) | 0.0811 (12) | −0.0020 (9) | −0.0135 (9) | −0.0121 (10) |
O2 | 0.0776 (11) | 0.0635 (10) | 0.0526 (9) | −0.0048 (9) | −0.0064 (8) | −0.0148 (8) |
O3 | 0.1097 (16) | 0.0810 (13) | 0.0739 (12) | 0.0203 (12) | 0.0118 (11) | −0.0300 (10) |
O4 | 0.0592 (10) | 0.0780 (12) | 0.0802 (12) | −0.0255 (9) | −0.0098 (9) | −0.0039 (9) |
O5 | 0.0487 (8) | 0.0681 (10) | 0.0497 (9) | −0.0089 (7) | 0.0043 (6) | −0.0031 (7) |
O6 | 0.0704 (11) | 0.1223 (16) | 0.0468 (9) | −0.0112 (11) | −0.0055 (8) | −0.0251 (10) |
Cl1 | 0.0555 (4) | 0.0787 (5) | 0.1069 (6) | −0.0068 (3) | 0.0290 (4) | 0.0040 (4) |
Cl2 | 0.0710 (4) | 0.0875 (5) | 0.0768 (4) | −0.0327 (4) | −0.0188 (3) | 0.0020 (3) |
Geometric parameters (Å, º) top
C1—C6 | 1.376 (3) | C9—C10 | 1.374 (3) |
C1—C2 | 1.380 (3) | C9—C14 | 1.374 (3) |
C1—C7 | 1.468 (3) | C9—C15 | 1.470 (3) |
C2—C3 | 1.376 (3) | C10—C11 | 1.378 (3) |
C2—C8 | 1.470 (3) | C10—C16 | 1.471 (3) |
C3—C4 | 1.382 (3) | C11—C12 | 1.380 (3) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.387 (3) | C12—C13 | 1.380 (3) |
C4—Cl2 | 1.729 (2) | C12—Cl1 | 1.731 (2) |
C5—C6 | 1.370 (3) | C13—C14 | 1.380 (3) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—O1 | 1.189 (3) | C15—O4 | 1.193 (3) |
C7—O2 | 1.388 (3) | C15—O5 | 1.386 (3) |
C8—O3 | 1.183 (3) | C16—O6 | 1.181 (3) |
C8—O2 | 1.393 (3) | C16—O5 | 1.395 (3) |
| | | |
C6—C1—C2 | 121.4 (2) | C10—C9—C15 | 107.64 (18) |
C6—C1—C7 | 130.8 (2) | C14—C9—C15 | 130.80 (19) |
C2—C1—C7 | 107.75 (19) | C9—C10—C11 | 122.18 (19) |
C3—C2—C1 | 121.8 (2) | C9—C10—C16 | 107.88 (18) |
C3—C2—C8 | 130.6 (2) | C11—C10—C16 | 129.9 (2) |
C1—C2—C8 | 107.5 (2) | C10—C11—C12 | 115.9 (2) |
C2—C3—C4 | 116.1 (2) | C10—C11—H11 | 122.0 |
C2—C3—H3 | 121.9 | C12—C11—H11 | 122.0 |
C4—C3—H3 | 121.9 | C13—C12—C11 | 122.3 (2) |
C3—C4—C5 | 122.3 (2) | C13—C12—Cl1 | 118.71 (18) |
C3—C4—Cl2 | 119.58 (19) | C11—C12—Cl1 | 118.95 (18) |
C5—C4—Cl2 | 118.08 (18) | C12—C13—C14 | 120.9 (2) |
C6—C5—C4 | 120.6 (2) | C12—C13—H13 | 119.5 |
C6—C5—H5 | 119.7 | C14—C13—H13 | 119.5 |
C4—C5—H5 | 119.7 | C9—C14—C13 | 117.1 (2) |
C5—C6—C1 | 117.6 (2) | C9—C14—H14 | 121.5 |
C5—C6—H6 | 121.2 | C13—C14—H14 | 121.5 |
C1—C6—H6 | 121.2 | O4—C15—O5 | 120.5 (2) |
O1—C7—O2 | 120.5 (2) | O4—C15—C9 | 131.7 (2) |
O1—C7—C1 | 131.8 (2) | O5—C15—C9 | 107.71 (17) |
O2—C7—C1 | 107.7 (2) | O6—C16—O5 | 120.5 (2) |
O3—C8—O2 | 120.8 (2) | O6—C16—C10 | 132.2 (2) |
O3—C8—C2 | 131.6 (3) | O5—C16—C10 | 107.27 (18) |
O2—C8—C2 | 107.58 (19) | C7—O2—C8 | 109.44 (18) |
C10—C9—C14 | 121.56 (19) | C15—O5—C16 | 109.48 (16) |
| | | |
C6—C1—C2—C3 | −1.9 (3) | C9—C10—C11—C12 | 0.1 (3) |
C7—C1—C2—C3 | 179.21 (18) | C16—C10—C11—C12 | −179.3 (2) |
C6—C1—C2—C8 | 176.22 (19) | C10—C11—C12—C13 | −1.3 (3) |
C7—C1—C2—C8 | −2.6 (2) | C10—C11—C12—Cl1 | 178.70 (15) |
C1—C2—C3—C4 | 0.8 (3) | C11—C12—C13—C14 | 1.4 (3) |
C8—C2—C3—C4 | −176.9 (2) | Cl1—C12—C13—C14 | −178.54 (17) |
C2—C3—C4—C5 | 1.5 (3) | C10—C9—C14—C13 | −0.8 (3) |
C2—C3—C4—Cl2 | −178.79 (15) | C15—C9—C14—C13 | 178.4 (2) |
C3—C4—C5—C6 | −2.7 (3) | C12—C13—C14—C9 | −0.3 (3) |
Cl2—C4—C5—C6 | 177.56 (16) | C10—C9—C15—O4 | 177.3 (2) |
C4—C5—C6—C1 | 1.5 (3) | C14—C9—C15—O4 | −2.0 (4) |
C2—C1—C6—C5 | 0.7 (3) | C10—C9—C15—O5 | −1.3 (2) |
C7—C1—C6—C5 | 179.3 (2) | C14—C9—C15—O5 | 179.3 (2) |
C6—C1—C7—O1 | 2.0 (4) | C9—C10—C16—O6 | 179.2 (3) |
C2—C1—C7—O1 | −179.3 (2) | C11—C10—C16—O6 | −1.4 (4) |
C6—C1—C7—O2 | −176.9 (2) | C9—C10—C16—O5 | −0.4 (2) |
C2—C1—C7—O2 | 1.8 (2) | C11—C10—C16—O5 | 179.0 (2) |
C3—C2—C8—O3 | 2.1 (4) | O1—C7—O2—C8 | −179.2 (2) |
C1—C2—C8—O3 | −175.8 (3) | C1—C7—O2—C8 | −0.1 (2) |
C3—C2—C8—O2 | −179.4 (2) | O3—C8—O2—C7 | 177.1 (2) |
C1—C2—C8—O2 | 2.6 (2) | C2—C8—O2—C7 | −1.5 (2) |
C14—C9—C10—C11 | 1.0 (3) | O4—C15—O5—C16 | −177.8 (2) |
C15—C9—C10—C11 | −178.46 (19) | C9—C15—O5—C16 | 1.1 (2) |
C14—C9—C10—C16 | −179.56 (19) | O6—C16—O5—C15 | 179.9 (2) |
C15—C9—C10—C16 | 1.0 (2) | C10—C16—O5—C15 | −0.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.80 | 3.292 (3) | 114 |
C6—H6···O6ii | 0.93 | 3.03 | 3.466 (3) | 111 |
C6—H6···O6iii | 0.93 | 2.89 | 3.690 (3) | 145 |
C11—H11···O2iv | 0.93 | 2.94 | 3.675 (3) | 137 |
C13—H13···O1 | 0.93 | 2.63 | 3.522 (3) | 161 |
C13—H13···O2 | 0.93 | 2.81 | 3.453 (3) | 127 |
C14—H14···O4v | 0.93 | 2.61 | 3.519 (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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.