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organic compounds
In the crystal structure of the title compound, C13H19ClO8, extensive intermolecular hydrogen bonding leads to a three-dimensional network, but the Cl substituent is not involved in these interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024706/sg2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024706/sg2041Isup2.hkl |
CCDC reference: 618324
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.033
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.50 From the CIF: _reflns_number_total 3896 Count of symmetry unique reflns 2235 Completeness (_total/calc) 174.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1661 Fraction of Friedel pairs measured 0.743 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.
Crystal data top
C13H19ClO8 | F(000) = 712 |
Mr = 338.74 | Dx = 1.465 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2300 reflections |
a = 7.3407 (5) Å | θ = 3–29° |
b = 13.5532 (14) Å | µ = 0.29 mm−1 |
c = 15.4384 (9) Å | T = 173 K |
V = 1536.0 (2) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.26 × 0.22 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2801 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.075 |
φ and ω scans | θmax = 28.5°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.93, Tmax = 0.94 | k = −18→18 |
46023 measured reflections | l = −20→20 |
3896 independent reflections |
Refinement top
Refinement on F | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = [1-(Fo-Fc)2/36σ2(F)]2/[2.46To(x)-
0.945T1(x) + 1.98T2(x)-0.132T3(x) + 0.288T4(x)],
where Ti are the Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994) |
wR(F2) = 0.033 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.20 e Å−3 |
2801 reflections | Δρmin = −0.18 e Å−3 |
200 parameters | Absolute structure: Flack (1983), with 1663 Friedel-pairs |
0 restraints | Absolute structure parameter: −0.01 (6) |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.17803 (9) | 0.77456 (5) | 0.70851 (3) | 0.0462 | |
C1 | −0.0403 (2) | 0.66542 (13) | 0.97976 (10) | 0.0218 | |
C2 | −0.1299 (2) | 0.56750 (12) | 0.99970 (10) | 0.0214 | |
C3 | 0.0022 (2) | 0.49744 (12) | 0.95621 (10) | 0.0190 | |
C4 | 0.1855 (2) | 0.54351 (12) | 0.97671 (10) | 0.0203 | |
C5 | 0.3353 (2) | 0.52188 (13) | 0.91281 (11) | 0.0254 | |
C6 | −0.0506 (3) | 0.79044 (13) | 0.87353 (12) | 0.0250 | |
C7 | −0.1898 (3) | 0.83112 (14) | 0.81275 (11) | 0.0284 | |
C8 | 0.3415 (3) | 0.63447 (13) | 0.79545 (12) | 0.0271 | |
C9 | 0.2838 (3) | 0.64797 (17) | 0.70370 (13) | 0.0392 | |
C10 | −0.1312 (2) | 0.33920 (13) | 0.95749 (10) | 0.0221 | |
C11 | −0.1098 (3) | 0.23765 (13) | 0.99245 (13) | 0.0278 | |
C12 | −0.2618 (3) | 0.50901 (14) | 1.13072 (11) | 0.0263 | |
C13 | −0.2348 (3) | 0.50509 (18) | 1.22664 (12) | 0.0394 | |
O1 | −0.09964 (18) | 0.69256 (9) | 0.89716 (8) | 0.0253 | |
O2 | 0.15018 (16) | 0.64701 (9) | 0.98146 (8) | 0.0236 | |
O3 | 0.28216 (16) | 0.54702 (9) | 0.82603 (8) | 0.0249 | |
O4 | 0.4309 (2) | 0.69079 (12) | 0.83609 (10) | 0.0433 | |
O5 | −0.00059 (17) | 0.39937 (8) | 0.99004 (8) | 0.0217 | |
O6 | −0.24413 (18) | 0.36722 (10) | 0.90784 (9) | 0.0292 | |
O7 | −0.12075 (17) | 0.55489 (10) | 1.09188 (8) | 0.0254 | |
O8 | −0.3907 (2) | 0.47818 (12) | 1.09234 (9) | 0.0400 | |
H11 | −0.0696 | 0.7170 | 1.0195 | 0.0220* | |
H21 | −0.2546 | 0.5586 | 0.9826 | 0.0223* | |
H31 | −0.0280 | 0.4906 | 0.8969 | 0.0203* | |
H41 | 0.2332 | 0.5153 | 1.0283 | 0.0211* | |
H51 | 0.4399 | 0.5610 | 0.9276 | 0.0273* | |
H52 | 0.3669 | 0.4531 | 0.9154 | 0.0273* | |
H61 | −0.0414 | 0.8301 | 0.9241 | 0.0262* | |
H62 | 0.0651 | 0.7895 | 0.8448 | 0.0262* | |
H71 | −0.1673 | 0.9007 | 0.8067 | 0.0298* | |
H72 | −0.3079 | 0.8211 | 0.8378 | 0.0298* | |
H91 | 0.1637 | 0.6213 | 0.6961 | 0.0483* | |
H92 | 0.2829 | 0.7170 | 0.6898 | 0.0483* | |
H93 | 0.3673 | 0.6142 | 0.6661 | 0.0483* | |
H111 | −0.0198 | 0.2029 | 0.9592 | 0.0346* | |
H112 | −0.0718 | 0.2409 | 1.0519 | 0.0346* | |
H113 | −0.2241 | 0.2035 | 0.9887 | 0.0346* | |
H131 | −0.1188 | 0.5344 | 1.2399 | 0.0420* | |
H132 | −0.3303 | 0.5423 | 1.2536 | 0.0420* | |
H133 | −0.2373 | 0.4382 | 1.2470 | 0.0420* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0582 (3) | 0.0568 (3) | 0.0236 (2) | 0.0061 (3) | 0.0007 (2) | 0.0029 (2) |
C1 | 0.0245 (8) | 0.0220 (8) | 0.0190 (7) | 0.0015 (7) | −0.0001 (6) | −0.0002 (6) |
C2 | 0.0208 (8) | 0.0247 (8) | 0.0187 (7) | −0.0017 (7) | −0.0017 (6) | 0.0027 (6) |
C3 | 0.0226 (8) | 0.0183 (8) | 0.0160 (7) | −0.0027 (6) | −0.0019 (6) | 0.0030 (6) |
C4 | 0.0216 (8) | 0.0203 (8) | 0.0190 (7) | −0.0009 (6) | −0.0034 (7) | 0.0024 (6) |
C5 | 0.0230 (8) | 0.0275 (9) | 0.0257 (8) | 0.0036 (7) | 0.0007 (7) | 0.0049 (7) |
C6 | 0.0284 (9) | 0.0196 (9) | 0.0271 (8) | 0.0003 (7) | 0.0014 (7) | 0.0019 (7) |
C7 | 0.0332 (10) | 0.0258 (9) | 0.0263 (8) | 0.0046 (8) | 0.0047 (8) | 0.0043 (7) |
C8 | 0.0274 (9) | 0.0257 (8) | 0.0281 (8) | 0.0017 (7) | 0.0107 (8) | 0.0006 (7) |
C9 | 0.0468 (13) | 0.0418 (12) | 0.0289 (9) | 0.0053 (9) | 0.0040 (9) | 0.0082 (9) |
C10 | 0.0246 (8) | 0.0227 (8) | 0.0190 (7) | −0.0027 (7) | 0.0038 (7) | −0.0015 (6) |
C11 | 0.0295 (9) | 0.0223 (8) | 0.0317 (9) | −0.0044 (7) | 0.0002 (7) | 0.0032 (7) |
C12 | 0.0321 (9) | 0.0210 (8) | 0.0257 (8) | 0.0053 (7) | 0.0086 (7) | 0.0022 (7) |
C13 | 0.0486 (12) | 0.0459 (12) | 0.0237 (9) | 0.0094 (10) | 0.0109 (8) | 0.0042 (8) |
O1 | 0.0335 (7) | 0.0199 (6) | 0.0226 (6) | −0.0014 (5) | −0.0056 (5) | 0.0032 (5) |
O2 | 0.0225 (6) | 0.0198 (6) | 0.0284 (6) | −0.0036 (5) | −0.0016 (5) | −0.0023 (5) |
O3 | 0.0280 (6) | 0.0262 (6) | 0.0205 (6) | −0.0012 (5) | 0.0023 (5) | 0.0010 (5) |
O4 | 0.0523 (9) | 0.0409 (9) | 0.0367 (8) | −0.0211 (7) | 0.0091 (7) | −0.0027 (7) |
O5 | 0.0258 (6) | 0.0183 (5) | 0.0209 (6) | −0.0030 (5) | −0.0037 (5) | 0.0027 (4) |
O6 | 0.0300 (7) | 0.0267 (6) | 0.0309 (7) | −0.0054 (5) | −0.0079 (6) | 0.0018 (5) |
O7 | 0.0274 (6) | 0.0321 (7) | 0.0166 (5) | −0.0012 (5) | 0.0014 (5) | 0.0010 (5) |
O8 | 0.0378 (8) | 0.0497 (9) | 0.0325 (7) | −0.0160 (7) | 0.0052 (6) | 0.0058 (7) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.7847 (19) | C7—H72 | 0.959 |
C1—C2 | 1.513 (2) | C8—C9 | 1.490 (3) |
C1—O1 | 1.397 (2) | C8—O3 | 1.348 (2) |
C1—O2 | 1.421 (2) | C8—O4 | 1.186 (2) |
C1—H11 | 0.955 | C9—H91 | 0.960 |
C2—C3 | 1.515 (2) | C9—H92 | 0.960 |
C2—O7 | 1.435 (2) | C9—H93 | 0.960 |
C2—H21 | 0.960 | C10—C11 | 1.487 (2) |
C3—C4 | 1.516 (2) | C10—O5 | 1.355 (2) |
C3—O5 | 1.428 (2) | C10—O6 | 1.191 (2) |
C3—H31 | 0.946 | C11—H111 | 0.960 |
C4—C5 | 1.506 (2) | C11—H112 | 0.960 |
C4—O2 | 1.428 (2) | C11—H113 | 0.960 |
C4—H41 | 0.950 | C12—C13 | 1.495 (3) |
C5—O3 | 1.436 (2) | C12—O7 | 1.348 (2) |
C5—H52 | 0.961 | C12—O8 | 1.192 (2) |
C6—C7 | 1.493 (3) | C13—H132 | 0.958 |
C6—O1 | 1.422 (2) | C13—H133 | 0.960 |
C6—H62 | 0.958 | ||
C2—C1—O1 | 106.34 (13) | C6—C7—H72 | 108.3 |
C2—C1—O2 | 105.66 (14) | Cl1—C7—H72 | 110.3 |
O1—C1—O2 | 111.71 (13) | C9—C8—O3 | 110.43 (17) |
C2—C1—H11 | 114.5 | C9—C8—O4 | 125.54 (18) |
O1—C1—H11 | 108.9 | O3—C8—O4 | 124.01 (18) |
O2—C1—H11 | 109.8 | C8—C9—H91 | 109.4 |
C1—C2—C3 | 100.45 (14) | C8—C9—H92 | 109.5 |
C1—C2—O7 | 106.62 (13) | H91—C9—H92 | 109.5 |
C3—C2—O7 | 109.57 (13) | C8—C9—H93 | 109.5 |
C1—C2—H21 | 117.9 | H91—C9—H93 | 109.5 |
C3—C2—H21 | 114.2 | H92—C9—H93 | 109.5 |
O7—C2—H21 | 107.6 | C11—C10—O5 | 110.36 (14) |
C2—C3—C4 | 102.56 (13) | C11—C10—O6 | 127.02 (16) |
C2—C3—O5 | 114.33 (13) | O5—C10—O6 | 122.62 (16) |
C4—C3—O5 | 108.65 (13) | C10—C11—H111 | 109.4 |
C2—C3—H31 | 109.9 | C10—C11—H112 | 109.6 |
C4—C3—H31 | 116.8 | H111—C11—H112 | 109.5 |
O5—C3—H31 | 105.0 | C10—C11—H113 | 109.4 |
C3—C4—C5 | 115.53 (14) | H111—C11—H113 | 109.5 |
C3—C4—O2 | 104.72 (13) | H112—C11—H113 | 109.5 |
C5—C4—O2 | 110.94 (13) | C13—C12—O7 | 110.78 (18) |
C3—C4—H41 | 109.7 | C13—C12—O8 | 125.82 (18) |
C5—C4—H41 | 101.6 | O7—C12—O8 | 123.38 (16) |
O2—C4—H41 | 114.8 | C12—C13—H132 | 108.3 |
C4—C5—O3 | 111.48 (14) | C12—C13—H133 | 110.9 |
C4—C5—H52 | 109.7 | H132—C13—H133 | 109.9 |
O3—C5—H52 | 109.5 | C6—O1—C1 | 113.63 (13) |
C7—C6—O1 | 109.42 (15) | C4—O2—C1 | 110.50 (12) |
C7—C6—H62 | 108.7 | C5—O3—C8 | 116.57 (14) |
O1—C6—H62 | 109.3 | C3—O5—C10 | 115.77 (13) |
C6—C7—Cl1 | 112.03 (13) | C2—O7—C12 | 117.38 (14) |
Intermolecular C—H···O interactions (Å, °) in (I) top
H···O | C···O | H—C···O | |
C1—H11···O4i | 2.56 | 3.453 (2) | 157 |
C9—H92···O6ii | 2.55 | 3.447 (3) | 156 |
C11—H113···O5iii | 2.48 | 3.428 (2) | 168 |
C7—H72···O4iv | 2.61 | 3.391 (3) | 139 |
C6—H61···O2v | 2.71 | 3.249 (2) | 117 |
Symmetry codes: (i) -1/2+x, 3/2-y, 2-z; (ii) -x, 1/2+y, 3/2-z; (iii) -1/2+x, 1/2-y, 2-z; (iv) x-1, y, z; (v) -1/2+x, 3/2-y, 2-z. |
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