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The structure of the carboxylic acid derivative of the new substituted open-cage system, 4,7-dichlorotricyclo[3.1.1.03,6]heptane-2-carboxylic acid, C8H8Cl2O2, shows that the carboxyl C atom has close contacts with C atoms of the cage system. Hydrogen bonds from the carboxylic acid functional groups of adjoining molecules form centrosymmetric dimers.
Supporting information
CCDC reference: 193749
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.110
- Data-to-parameter ratio = 13.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05
Absolute value of the parameter shift to su ratio given 0.053
Additional refinement cycles may be required.
PLAT_320 Alert C Check Hybridisation of C(1) in main residue ?
PLAT_320 Alert C Check Hybridisation of C(3) in main residue ?
PLAT_320 Alert C Check Hybridisation of C(5) in main residue ?
PLAT_320 Alert C Check Hybridisation of C(6) in main residue ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4,7-dichlorotricyclo[3.1.1.0
3,6]heptane-2-carboxylic acid
top
Crystal data top
C8H8Cl2O2 | F(000) = 848 |
Mr = 207.04 | Dx = 1.545 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.497 (7) Å | Cell parameters from 786 reflections |
b = 9.036 (3) Å | θ = 2.3–28.1° |
c = 10.084 (3) Å | µ = 0.68 mm−1 |
β = 114.673 (6)° | T = 294 K |
V = 1779.9 (10) Å3 | Irregular plate, colourless |
Z = 8 | 0.42 × 0.40 × 0.10 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 1822 independent reflections |
Radiation source: fine-focus sealed tube | 1512 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: integration (Wuensch & Prewett, 1965) | h = −24→26 |
Tmin = 0.740, Tmax = 0.935 | k = −11→6 |
5852 measured reflections | l = −12→9 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0521P)2 + 1.6743P] where P = (Fo2 + 2Fc2)/3 |
1822 reflections | (Δ/σ)max = 0.053 |
140 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.32 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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C | 0.69894 (11) | 0.3240 (2) | 0.8074 (2) | 0.0463 (5) | |
O1 | 0.67660 (9) | 0.3515 (2) | 0.90279 (18) | 0.0651 (5) | |
H1O | 0.698 (2) | 0.329 (4) | 0.979 (4) | 0.098* | |
O2 | 0.75173 (9) | 0.2508 (2) | 0.83185 (18) | 0.0691 (5) | |
C1 | 0.57922 (11) | 0.3803 (2) | 0.5909 (2) | 0.0501 (5) | |
H1 | 0.5564 (13) | 0.462 (3) | 0.610 (3) | 0.054 (6)* | |
C2 | 0.65817 (11) | 0.3850 (2) | 0.6576 (2) | 0.0481 (5) | |
H2 | 0.6734 (12) | 0.491 (3) | 0.661 (2) | 0.053 (6)* | |
C3 | 0.65920 (11) | 0.3098 (2) | 0.5222 (2) | 0.0481 (5) | |
H3 | 0.6939 (12) | 0.340 (3) | 0.491 (3) | 0.050 (6)* | |
C4 | 0.64305 (12) | 0.1441 (2) | 0.5147 (2) | 0.0485 (5) | |
H4 | 0.6661 (11) | 0.084 (2) | 0.600 (2) | 0.043 (5)* | |
Cl4 | 0.65773 (4) | 0.06093 (9) | 0.36914 (8) | 0.0810 (3) | |
C5 | 0.56682 (12) | 0.1774 (3) | 0.4653 (2) | 0.0506 (5) | |
H5 | 0.5357 (14) | 0.118 (3) | 0.397 (3) | 0.062 (7)* | |
C6 | 0.58089 (12) | 0.3426 (3) | 0.4415 (2) | 0.0534 (6) | |
H6 | 0.5604 (13) | 0.397 (3) | 0.360 (3) | 0.057 (7)* | |
C7 | 0.55132 (11) | 0.2249 (3) | 0.5938 (3) | 0.0510 (5) | |
H7 | 0.5703 (12) | 0.166 (3) | 0.685 (3) | 0.048 (6)* | |
Cl7 | 0.46051 (3) | 0.23276 (9) | 0.53865 (9) | 0.0782 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C | 0.0440 (11) | 0.0449 (10) | 0.0419 (11) | −0.0037 (9) | 0.0101 (9) | −0.0055 (8) |
O1 | 0.0570 (10) | 0.0853 (13) | 0.0431 (9) | 0.0195 (9) | 0.0111 (7) | −0.0046 (8) |
O2 | 0.0531 (10) | 0.1012 (14) | 0.0477 (9) | 0.0232 (9) | 0.0157 (8) | 0.0024 (9) |
C1 | 0.0481 (12) | 0.0449 (11) | 0.0468 (12) | 0.0083 (9) | 0.0096 (9) | 0.0072 (9) |
C2 | 0.0484 (12) | 0.0389 (11) | 0.0473 (11) | −0.0038 (9) | 0.0104 (9) | 0.0014 (8) |
C3 | 0.0461 (11) | 0.0529 (12) | 0.0415 (11) | −0.0094 (9) | 0.0143 (9) | 0.0045 (9) |
C4 | 0.0513 (12) | 0.0486 (12) | 0.0441 (11) | −0.0024 (10) | 0.0186 (9) | −0.0032 (9) |
Cl4 | 0.0805 (5) | 0.0957 (5) | 0.0758 (5) | −0.0176 (4) | 0.0415 (4) | −0.0349 (4) |
C5 | 0.0464 (12) | 0.0514 (12) | 0.0465 (12) | −0.0096 (10) | 0.0120 (10) | −0.0008 (10) |
C6 | 0.0512 (12) | 0.0543 (13) | 0.0420 (11) | −0.0021 (10) | 0.0069 (10) | 0.0141 (10) |
C7 | 0.0406 (11) | 0.0558 (13) | 0.0531 (12) | 0.0064 (9) | 0.0162 (9) | 0.0133 (10) |
Cl7 | 0.0464 (4) | 0.0873 (5) | 0.1000 (6) | 0.0056 (3) | 0.0297 (4) | 0.0200 (4) |
Geometric parameters (Å, º) top
C—O2 | 1.246 (3) | C3—C6 | 1.562 (3) |
C—O1 | 1.266 (3) | C3—H3 | 0.96 (2) |
C—C2 | 1.500 (3) | C4—C5 | 1.531 (3) |
O1—H1O | 0.74 (4) | C4—Cl4 | 1.791 (2) |
C1—C7 | 1.532 (3) | C4—H4 | 0.96 (2) |
C1—C2 | 1.543 (3) | C5—C7 | 1.527 (3) |
C1—C6 | 1.559 (3) | C5—C6 | 1.561 (3) |
C1—H1 | 0.95 (2) | C5—H5 | 0.91 (3) |
C2—C3 | 1.533 (3) | C6—H6 | 0.90 (3) |
C2—H2 | 1.01 (2) | C7—Cl7 | 1.794 (2) |
C3—C4 | 1.532 (3) | C7—H7 | 0.99 (2) |
| | | |
O2—C—O1 | 123.8 (2) | C5—C4—Cl4 | 110.30 (16) |
O2—C—C2 | 119.7 (2) | C3—C4—Cl4 | 109.66 (16) |
O1—C—C2 | 116.5 (2) | C5—C4—H4 | 119.2 (13) |
C—O1—H1O | 118 (3) | C3—C4—H4 | 119.2 (13) |
C7—C1—C2 | 112.65 (17) | Cl4—C4—H4 | 106.9 (13) |
C7—C1—C6 | 89.15 (17) | C7—C5—C4 | 111.24 (18) |
C2—C1—C6 | 87.86 (17) | C7—C5—C6 | 89.25 (18) |
C7—C1—H1 | 118.0 (14) | C4—C5—C6 | 89.34 (17) |
C2—C1—H1 | 117.2 (15) | C7—C5—H5 | 117.3 (16) |
C6—C1—H1 | 126.0 (14) | C4—C5—H5 | 118.6 (17) |
C—C2—C3 | 120.99 (19) | C6—C5—H5 | 125.0 (16) |
C—C2—C1 | 120.21 (19) | C1—C6—C5 | 88.63 (16) |
C3—C2—C1 | 91.24 (16) | C1—C6—C3 | 89.58 (16) |
C—C2—H2 | 105.8 (14) | C5—C6—C3 | 88.56 (17) |
C3—C2—H2 | 108.8 (13) | C1—C6—H6 | 124.0 (16) |
C1—C2—H2 | 108.9 (14) | C5—C6—H6 | 127.8 (16) |
C4—C3—C2 | 112.91 (17) | C3—C6—H6 | 126.2 (16) |
C4—C3—C6 | 89.24 (16) | C5—C7—C1 | 90.89 (17) |
C2—C3—C6 | 88.10 (17) | C5—C7—Cl7 | 110.04 (16) |
C4—C3—H3 | 116.7 (14) | C1—C7—Cl7 | 110.01 (15) |
C2—C3—H3 | 118.1 (14) | C5—C7—H7 | 119.0 (13) |
C6—C3—H3 | 126.1 (14) | C1—C7—H7 | 119.7 (13) |
C5—C4—C3 | 90.76 (17) | Cl7—C7—H7 | 106.4 (13) |
| | | |
O2—C—C2—C3 | 26.8 (3) | C7—C1—C6—C5 | −10.76 (16) |
O1—C—C2—C3 | −153.2 (2) | C2—C1—C6—C5 | 101.94 (16) |
O2—C—C2—C1 | 139.1 (2) | C7—C1—C6—C3 | −99.32 (16) |
O1—C—C2—C1 | −40.9 (3) | C2—C1—C6—C3 | 13.38 (16) |
C7—C1—C2—C | −52.9 (3) | C7—C5—C6—C1 | 10.79 (16) |
C6—C1—C2—C | −141.1 (2) | C4—C5—C6—C1 | −100.47 (16) |
C7—C1—C2—C3 | 74.6 (2) | C7—C5—C6—C3 | 100.40 (17) |
C6—C1—C2—C3 | −13.64 (16) | C4—C5—C6—C3 | −10.86 (17) |
C—C2—C3—C4 | 52.1 (3) | C4—C3—C6—C1 | 99.49 (16) |
C1—C2—C3—C4 | −74.8 (2) | C2—C3—C6—C1 | −13.46 (16) |
C—C2—C3—C6 | 140.5 (2) | C4—C3—C6—C5 | 10.85 (17) |
C1—C2—C3—C6 | 13.61 (16) | C2—C3—C6—C5 | −102.10 (17) |
C2—C3—C4—C5 | 76.6 (2) | C4—C5—C7—C1 | 78.0 (2) |
C6—C3—C4—C5 | −11.06 (17) | C6—C5—C7—C1 | −10.98 (16) |
C2—C3—C4—Cl4 | −171.53 (15) | C4—C5—C7—Cl7 | −170.28 (15) |
C6—C3—C4—Cl4 | 100.85 (17) | C6—C5—C7—Cl7 | 100.73 (16) |
C3—C4—C5—C7 | −77.9 (2) | C2—C1—C7—C5 | −76.3 (2) |
Cl4—C4—C5—C7 | 170.80 (15) | C6—C1—C7—C5 | 10.99 (16) |
C3—C4—C5—C6 | 11.07 (17) | C2—C1—C7—Cl7 | 171.93 (16) |
Cl4—C4—C5—C6 | −100.26 (17) | C6—C1—C7—Cl7 | −100.74 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.74 (4) | 1.90 (4) | 2.636 (3) | 173 (4) |
Symmetry code: (i) −x+3/2, −y+1/2, −z+2. |
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