Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033045/bt6565sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033045/bt6565Isup2.hkl |
CCDC reference: 262479
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.150
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997) and PLUTON (Spek, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C9H16O4 | Z = 2 |
Mr = 188.22 | F(000) = 204 |
Triclinic, P1 | Dx = 1.145 Mg m−3 |
Hall symbol: -P 1 | Melting point: 432 K |
a = 7.683 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.549 (1) Å | Cell parameters from 3369 reflections |
c = 9.382 (1) Å | θ = 5–55° |
α = 76.249 (2)° | µ = 0.09 mm−1 |
β = 70.140 (2)° | T = 293 K |
γ = 72.355 (2)° | Block, colourless |
V = 546.05 (12) Å3 | 0.55 × 0.22 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 2261 independent reflections |
Radiation source: fine-focus sealed tube | 1784 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 27.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.977, Tmax = 0.989 | k = −10→11 |
5840 measured reflections | l = −12→12 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0805P)2 + 0.0901P] where P = (Fo2 + 2Fc2)/3 |
2261 reflections | (Δ/σ)max < 0.001 |
126 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = -0.80858(0.00061) m2 = 0.58695(0.00074) m3 = -0.04113(0.00319) D = -2.45341(0.01993) Atom d s d/s (d/s)**2 C2 * -0.0049 0.0016 - 2.988 8.929 C7 * 0.0064 0.0019 3.405 11.596 C8 * 0.0165 0.0030 5.578 31.111 C9 * -0.0226 0.0035 - 6.509 42.367 C3 1.2007 0.0018 673.727 453907.656 C1 0.1351 0.0017 77.893 6067.362 ============ Sum((d/s)**2) for starred atoms 94.004 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 2 m1 = 0.66339(0.00070) m2 = 0.73921(0.00047) m3 = -0.11617(0.00266) D = 5.02160(0.01959) Atom d s d/s (d/s)**2 C2 * -0.0040 0.0016 - 2.454 6.023 C4 * 0.0048 0.0017 2.812 7.910 C5 * 0.0057 0.0020 2.791 7.791 C6 * -0.0109 0.0027 - 4.051 16.412 C1 - 1.2935 0.0017 - 758.805 575784.375 C3 - 0.0502 0.0017 - 28.886 834.402 ============ Sum((d/s)**2) for starred atoms 38.136 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 3 m1 = 0.56743(0.00075) m2 = 0.82342(0.00052) m3 = -0.00125(0.00084) D = 5.55989(0.00462) Atom d s d/s (d/s)**2 C2 * 0.0022 0.0016 1.355 1.837 C3 * -0.0088 0.0017 - 5.133 26.345 O2 * 0.0024 0.0016 1.523 2.321 O4 * 0.0022 0.0014 1.622 2.632 C7 1.3285 0.0018 750.870 563805.125 C4 - 0.2488 0.0017 - 147.142 21650.768 ============ Sum((d/s)**2) for starred atoms 33.135 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 4 m1 = 0.68202(0.00075) m2 = -0.72881(0.00070) m3 = -0.06078(0.00094) D = 0.67894(0.00888) Atom d s d/s (d/s)**2 C2 * 0.0026 0.0016 1.620 2.623 C1 * -0.0105 0.0017 - 6.119 37.447 O3 * 0.0032 0.0015 2.128 4.529 O1 * 0.0032 0.0016 1.942 3.773 C7 - 0.3378 0.0018 - 185.574 34437.633 C4 1.3846 0.0017 809.940 656002.313 ============ Sum((d/s)**2) for starred atoms 48.372 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 84.39 (0.06) 95.61 (0.06) 1 3 88.59 (0.06) 91.41 (0.06) 1 4 12.38 (0.11) 167.62 (0.11) 2 3 9.85 (0.11) 170.15 (0.11) 2 4 85.46 (0.06) 94.54 (0.06) 3 4 77.70 (0.06) 102.30 (0.06) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0860 (2) | 0.07364 (18) | 0.79604 (14) | 0.0766 (5) | |
O2 | −0.03567 (18) | 0.44811 (19) | 0.71039 (15) | 0.0784 (5) | |
O3 | 0.1097 (2) | 0.13697 (17) | 1.00235 (13) | 0.0745 (4) | |
O4 | 0.20931 (16) | 0.39020 (17) | 0.50464 (12) | 0.0706 (4) | |
C1 | 0.1404 (2) | 0.1565 (2) | 0.86526 (17) | 0.0512 (4) | |
C2 | 0.2539 (2) | 0.27809 (19) | 0.75464 (16) | 0.0491 (4) | |
C3 | 0.1413 (2) | 0.3764 (2) | 0.64235 (17) | 0.0538 (4) | |
C4 | 0.4476 (2) | 0.1756 (2) | 0.66546 (17) | 0.0533 (4) | |
H4A | 0.4227 | 0.1063 | 0.6101 | 0.064* | |
H4B | 0.5164 | 0.2520 | 0.5901 | 0.064* | |
C5 | 0.5761 (3) | 0.0656 (2) | 0.7608 (2) | 0.0655 (5) | |
H5A | 0.6061 | 0.1335 | 0.8142 | 0.079* | |
H5B | 0.5093 | −0.0116 | 0.8370 | 0.079* | |
C6 | 0.7584 (3) | −0.0302 (3) | 0.6626 (3) | 0.0911 (7) | |
H6A | 0.8364 | −0.0989 | 0.7261 | 0.137* | |
H6B | 0.8259 | 0.0459 | 0.5884 | 0.137* | |
H6C | 0.7291 | −0.0988 | 0.6107 | 0.137* | |
C7 | 0.2733 (2) | 0.3985 (2) | 0.84349 (18) | 0.0576 (4) | |
H7A | 0.1474 | 0.4486 | 0.9053 | 0.069* | |
H7B | 0.3481 | 0.3359 | 0.9127 | 0.069* | |
C8 | 0.3661 (4) | 0.5356 (3) | 0.7421 (3) | 0.0910 (7) | |
H8A | 0.4900 | 0.4855 | 0.6776 | 0.109* | |
H8B | 0.2887 | 0.6007 | 0.6755 | 0.109* | |
C9 | 0.3916 (5) | 0.6487 (3) | 0.8279 (3) | 0.1129 (9) | |
H9A | 0.4502 | 0.7321 | 0.7566 | 0.169* | |
H9B | 0.4715 | 0.5860 | 0.8918 | 0.169* | |
H9C | 0.2694 | 0.7009 | 0.8905 | 0.169* | |
H1 | 0.026 (4) | 0.006 (3) | 0.856 (3) | 0.108 (8)* | |
H2 | −0.094 (4) | 0.508 (3) | 0.642 (3) | 0.101 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1062 (11) | 0.0927 (10) | 0.0492 (7) | −0.0677 (9) | −0.0236 (7) | 0.0136 (6) |
O2 | 0.0509 (7) | 0.1039 (10) | 0.0483 (7) | −0.0003 (6) | −0.0057 (5) | 0.0108 (7) |
O3 | 0.0966 (10) | 0.0984 (10) | 0.0427 (7) | −0.0646 (8) | −0.0189 (6) | 0.0148 (6) |
O4 | 0.0534 (7) | 0.0920 (9) | 0.0435 (7) | −0.0091 (6) | −0.0073 (5) | 0.0107 (6) |
C1 | 0.0504 (8) | 0.0590 (9) | 0.0436 (8) | −0.0238 (7) | −0.0150 (7) | 0.0091 (6) |
C2 | 0.0456 (8) | 0.0553 (8) | 0.0411 (8) | −0.0204 (7) | −0.0074 (6) | 0.0057 (6) |
C3 | 0.0475 (8) | 0.0579 (9) | 0.0445 (8) | −0.0185 (7) | −0.0054 (6) | 0.0089 (6) |
C4 | 0.0491 (9) | 0.0610 (9) | 0.0457 (8) | −0.0169 (7) | −0.0101 (7) | −0.0010 (7) |
C5 | 0.0606 (10) | 0.0743 (11) | 0.0641 (11) | −0.0102 (8) | −0.0250 (8) | −0.0127 (9) |
C6 | 0.0683 (13) | 0.1114 (17) | 0.0927 (15) | 0.0091 (12) | −0.0359 (11) | −0.0354 (13) |
C7 | 0.0573 (9) | 0.0600 (10) | 0.0492 (9) | −0.0237 (8) | −0.0031 (7) | −0.0028 (7) |
C8 | 0.1131 (18) | 0.0881 (14) | 0.0772 (14) | −0.0656 (14) | −0.0043 (12) | −0.0034 (11) |
C9 | 0.132 (2) | 0.0840 (16) | 0.124 (2) | −0.0580 (16) | −0.0058 (17) | −0.0237 (15) |
O1—C1 | 1.297 (2) | C5—H5A | 0.9700 |
O1—H1 | 0.83 (3) | C5—H5B | 0.9700 |
O2—C3 | 1.313 (2) | C6—H6A | 0.9600 |
O2—H2 | 0.88 (3) | C6—H6B | 0.9600 |
O3—C1 | 1.2056 (18) | C6—H6C | 0.9600 |
O4—C3 | 1.2093 (18) | C7—C8 | 1.517 (2) |
C1—C2 | 1.5297 (19) | C7—H7A | 0.9700 |
C2—C3 | 1.524 (2) | C7—H7B | 0.9700 |
C2—C7 | 1.537 (2) | C8—C9 | 1.487 (3) |
C2—C4 | 1.547 (2) | C8—H8A | 0.9700 |
C4—C5 | 1.515 (2) | C8—H8B | 0.9700 |
C4—H4A | 0.9700 | C9—H9A | 0.9600 |
C4—H4B | 0.9700 | C9—H9B | 0.9600 |
C5—C6 | 1.506 (3) | C9—H9C | 0.9600 |
C1—O1—H1 | 113.2 (18) | H5A—C5—H5B | 108.0 |
C3—O2—H2 | 110.4 (17) | C5—C6—H6A | 109.5 |
O3—C1—O1 | 123.73 (14) | C5—C6—H6B | 109.5 |
O3—C1—C2 | 123.18 (14) | H6A—C6—H6B | 109.5 |
O1—C1—C2 | 113.06 (13) | C5—C6—H6C | 109.5 |
C3—C2—C1 | 107.15 (12) | H6A—C6—H6C | 109.5 |
C3—C2—C7 | 109.01 (13) | H6B—C6—H6C | 109.5 |
C1—C2—C7 | 109.91 (12) | C8—C7—C2 | 114.01 (14) |
C3—C2—C4 | 109.01 (12) | C8—C7—H7A | 108.8 |
C1—C2—C4 | 107.97 (13) | C2—C7—H7A | 108.8 |
C7—C2—C4 | 113.58 (13) | C8—C7—H7B | 108.8 |
O4—C3—O2 | 123.42 (15) | C2—C7—H7B | 108.8 |
O4—C3—C2 | 123.45 (14) | H7A—C7—H7B | 107.6 |
O2—C3—C2 | 113.11 (13) | C9—C8—C7 | 114.15 (19) |
C5—C4—C2 | 116.08 (13) | C9—C8—H8A | 108.7 |
C5—C4—H4A | 108.3 | C7—C8—H8A | 108.7 |
C2—C4—H4A | 108.3 | C9—C8—H8B | 108.7 |
C5—C4—H4B | 108.3 | C7—C8—H8B | 108.7 |
C2—C4—H4B | 108.3 | H8A—C8—H8B | 107.6 |
H4A—C4—H4B | 107.4 | C8—C9—H9A | 109.5 |
C6—C5—C4 | 111.42 (16) | C8—C9—H9B | 109.5 |
C6—C5—H5A | 109.3 | H9A—C9—H9B | 109.5 |
C4—C5—H5A | 109.3 | C8—C9—H9C | 109.5 |
C6—C5—H5B | 109.3 | H9A—C9—H9C | 109.5 |
C4—C5—H5B | 109.3 | H9B—C9—H9C | 109.5 |
O3—C1—C2—C3 | −133.23 (17) | C7—C2—C3—O2 | −64.83 (17) |
O1—C1—C2—C3 | 48.74 (18) | C4—C2—C3—O2 | 170.68 (14) |
O3—C1—C2—C7 | −14.9 (2) | C3—C2—C4—C5 | −178.15 (14) |
O1—C1—C2—C7 | 167.06 (14) | C1—C2—C4—C5 | −62.07 (18) |
O3—C1—C2—C4 | 109.48 (18) | C7—C2—C4—C5 | 60.09 (18) |
O1—C1—C2—C4 | −68.55 (17) | C2—C4—C5—C6 | 178.96 (16) |
C1—C2—C3—O4 | −127.53 (17) | C3—C2—C7—C8 | −56.9 (2) |
C7—C2—C3—O4 | 113.56 (18) | C1—C2—C7—C8 | −174.03 (17) |
C4—C2—C3—O4 | −10.9 (2) | C4—C2—C7—C8 | 64.9 (2) |
C1—C2—C3—O2 | 54.07 (18) | C2—C7—C8—C9 | −177.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.83 (3) | 1.85 (3) | 2.678 (2) | 176 (3) |
O2—H2···O4ii | 0.87 (3) | 1.80 (3) | 2.673 (2) | 175 (3) |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x, −y+1, −z+1. |