Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003461/ci2002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003461/ci2002Isup2.hkl |
CCDC reference: 601137
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - C14 .. 7.27 su
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.645 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.58 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.64 e/A 3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C18H18O4 | F(000) = 632 |
Mr = 298.32 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5611 reflections |
a = 13.5136 (4) Å | θ = 2.8–25.0° |
b = 7.8414 (3) Å | µ = 0.09 mm−1 |
c = 14.9854 (5) Å | T = 120 K |
β = 109.823 (2)° | Rhombohedral, yellow |
V = 1493.84 (9) Å3 | 0.68 × 0.66 × 0.48 mm |
Z = 4 |
Brucker SMART APEX2 CCD area-detector diffractometer | 2632 independent reflections |
Radiation source: fine-focus sealed tube | 2394 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.8° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −9→9 |
Tmin = 0.862, Tmax = 0.957 | l = −17→17 |
13327 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.034P)2 + 1.0117P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2632 reflections | Δρmax = 0.65 e Å−3 |
203 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0095 (13) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.04274 (8) | 0.30260 (13) | 0.49490 (7) | 0.0269 (3) | |
O2 | 0.30832 (8) | 0.64014 (14) | 0.17284 (7) | 0.0254 (3) | |
O3 | 0.47653 (8) | 0.79725 (13) | 0.29036 (7) | 0.0243 (3) | |
O4 | 0.51875 (8) | 0.80019 (13) | 0.47994 (7) | 0.0262 (3) | |
C1 | 0.18572 (11) | 0.49287 (18) | 0.72405 (10) | 0.0224 (3) | |
H1 | 0.2409 | 0.5494 | 0.7100 | 0.027* | |
C2 | 0.18054 (11) | 0.50241 (19) | 0.81491 (10) | 0.0244 (3) | |
H2 | 0.2316 | 0.5665 | 0.8624 | 0.029* | |
C3 | 0.10126 (11) | 0.41885 (19) | 0.83652 (10) | 0.0241 (3) | |
H3 | 0.0978 | 0.4255 | 0.8987 | 0.029* | |
C4 | 0.02679 (11) | 0.32519 (19) | 0.76682 (10) | 0.0251 (3) | |
H4 | −0.0273 | 0.2669 | 0.7816 | 0.030* | |
C5 | 0.03117 (11) | 0.31655 (18) | 0.67607 (10) | 0.0229 (3) | |
H5 | −0.0203 | 0.2527 | 0.6288 | 0.027* | |
C6 | 0.11053 (11) | 0.40087 (17) | 0.65322 (10) | 0.0199 (3) | |
C7 | 0.11017 (11) | 0.38856 (18) | 0.55327 (10) | 0.0206 (3) | |
C8 | 0.19210 (11) | 0.47937 (18) | 0.52712 (10) | 0.0219 (3) | |
H8 | 0.2445 | 0.5423 | 0.5741 | 0.026* | |
C9 | 0.19381 (11) | 0.47465 (18) | 0.43858 (10) | 0.0215 (3) | |
H9 | 0.1393 | 0.4115 | 0.3938 | 0.026* | |
C10 | 0.27044 (11) | 0.55594 (18) | 0.40290 (10) | 0.0203 (3) | |
C11 | 0.25183 (11) | 0.55209 (18) | 0.30529 (10) | 0.0210 (3) | |
H11 | 0.1916 | 0.4949 | 0.2642 | 0.025* | |
C12 | 0.32140 (11) | 0.63196 (18) | 0.26823 (9) | 0.0202 (3) | |
C13 | 0.41110 (11) | 0.71328 (18) | 0.32859 (10) | 0.0201 (3) | |
C14 | 0.42983 (11) | 0.71604 (18) | 0.42681 (10) | 0.0203 (3) | |
C15 | 0.35989 (11) | 0.63815 (18) | 0.46358 (10) | 0.0207 (3) | |
H15 | 0.3727 | 0.6406 | 0.5299 | 0.025* | |
C16 | 0.21490 (13) | 0.5707 (2) | 0.10838 (10) | 0.0329 (4) | |
H16A | 0.2149 | 0.5851 | 0.0434 | 0.049* | |
H16B | 0.1540 | 0.6299 | 0.1153 | 0.049* | |
H16C | 0.2110 | 0.4490 | 0.1217 | 0.049* | |
C17 | 0.57785 (12) | 0.7181 (2) | 0.31140 (11) | 0.0286 (4) | |
H17A | 0.6197 | 0.7824 | 0.2809 | 0.043* | |
H17B | 0.5688 | 0.6007 | 0.2875 | 0.043* | |
H17C | 0.6141 | 0.7171 | 0.3802 | 0.043* | |
C18 | 0.54150 (12) | 0.8014 (2) | 0.58011 (10) | 0.0288 (4) | |
H18A | 0.6072 | 0.8636 | 0.6107 | 0.043* | |
H18B | 0.5490 | 0.6838 | 0.6037 | 0.043* | |
H18C | 0.4840 | 0.8574 | 0.5947 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0271 (6) | 0.0286 (6) | 0.0257 (5) | −0.0064 (5) | 0.0096 (4) | −0.0061 (4) |
O2 | 0.0264 (5) | 0.0313 (6) | 0.0195 (5) | 0.0008 (4) | 0.0090 (4) | 0.0041 (4) |
O3 | 0.0244 (5) | 0.0257 (6) | 0.0239 (5) | −0.0005 (4) | 0.0097 (4) | 0.0055 (4) |
O4 | 0.0291 (6) | 0.0281 (6) | 0.0229 (5) | −0.0058 (5) | 0.0107 (4) | −0.0003 (4) |
C1 | 0.0223 (7) | 0.0206 (7) | 0.0254 (7) | −0.0013 (6) | 0.0093 (6) | 0.0006 (6) |
C2 | 0.0260 (7) | 0.0227 (7) | 0.0228 (7) | −0.0005 (6) | 0.0058 (6) | −0.0010 (6) |
C3 | 0.0285 (8) | 0.0238 (7) | 0.0212 (7) | 0.0041 (6) | 0.0099 (6) | 0.0041 (6) |
C4 | 0.0220 (7) | 0.0267 (8) | 0.0279 (8) | 0.0005 (6) | 0.0101 (6) | 0.0062 (6) |
C5 | 0.0200 (7) | 0.0228 (7) | 0.0238 (7) | −0.0002 (6) | 0.0048 (6) | 0.0027 (6) |
C6 | 0.0194 (7) | 0.0171 (7) | 0.0229 (7) | 0.0034 (6) | 0.0067 (6) | 0.0022 (6) |
C7 | 0.0196 (7) | 0.0175 (7) | 0.0237 (7) | 0.0030 (6) | 0.0060 (6) | 0.0006 (6) |
C8 | 0.0205 (7) | 0.0215 (7) | 0.0228 (7) | −0.0006 (6) | 0.0063 (6) | −0.0004 (6) |
C9 | 0.0207 (7) | 0.0187 (7) | 0.0238 (7) | 0.0010 (6) | 0.0057 (6) | 0.0000 (6) |
C10 | 0.0215 (7) | 0.0178 (7) | 0.0216 (7) | 0.0032 (6) | 0.0073 (6) | 0.0012 (6) |
C11 | 0.0202 (7) | 0.0197 (7) | 0.0212 (7) | 0.0012 (6) | 0.0046 (6) | −0.0015 (6) |
C12 | 0.0246 (7) | 0.0192 (7) | 0.0164 (7) | 0.0051 (6) | 0.0064 (6) | 0.0008 (5) |
C13 | 0.0217 (7) | 0.0179 (7) | 0.0214 (7) | 0.0029 (6) | 0.0083 (6) | 0.0033 (6) |
C14 | 0.0191 (7) | 0.0178 (7) | 0.0216 (7) | 0.0005 (6) | 0.0036 (5) | −0.0005 (6) |
C15 | 0.0237 (7) | 0.0209 (7) | 0.0174 (7) | 0.0021 (6) | 0.0066 (6) | 0.0011 (6) |
C16 | 0.0408 (9) | 0.0370 (9) | 0.0190 (7) | −0.0053 (8) | 0.0076 (7) | −0.0022 (7) |
C17 | 0.0245 (8) | 0.0358 (9) | 0.0276 (8) | −0.0001 (7) | 0.0114 (6) | 0.0014 (7) |
C18 | 0.0285 (8) | 0.0322 (9) | 0.0214 (8) | −0.0059 (7) | 0.0028 (6) | −0.0030 (6) |
O1—C7 | 1.2285 (17) | C8—H8 | 0.95 |
O2—C12 | 1.3810 (16) | C9—C10 | 1.463 (2) |
O2—C16 | 1.4129 (19) | C9—H9 | 0.95 |
O3—C13 | 1.3737 (17) | C10—C11 | 1.3980 (19) |
O3—C17 | 1.4376 (18) | C10—C15 | 1.399 (2) |
O4—C14 | 1.3654 (17) | C11—C12 | 1.392 (2) |
O4—C18 | 1.4265 (17) | C11—H11 | 0.95 |
C1—C2 | 1.389 (2) | C12—C13 | 1.397 (2) |
C1—C6 | 1.396 (2) | C13—C14 | 1.4065 (19) |
C1—H1 | 0.95 | C14—C15 | 1.387 (2) |
C2—C3 | 1.385 (2) | C15—H15 | 0.95 |
C2—H2 | 0.95 | C16—H16A | 0.98 |
C3—C4 | 1.389 (2) | C16—H16B | 0.98 |
C3—H3 | 0.95 | C16—H16C | 0.98 |
C4—C5 | 1.383 (2) | C17—H17A | 0.98 |
C4—H4 | 0.95 | C17—H17B | 0.98 |
C5—C6 | 1.398 (2) | C17—H17C | 0.98 |
C5—H5 | 0.95 | C18—H18A | 0.98 |
C6—C7 | 1.4992 (19) | C18—H18B | 0.98 |
C7—C8 | 1.477 (2) | C18—H18C | 0.98 |
C8—C9 | 1.335 (2) | ||
C12—O2—C16 | 117.44 (11) | C12—C11—C10 | 120.10 (13) |
C13—O3—C17 | 113.67 (11) | C12—C11—H11 | 120.0 |
C14—O4—C18 | 116.73 (11) | C10—C11—H11 | 120.0 |
C2—C1—C6 | 120.52 (13) | O2—C12—C11 | 124.54 (12) |
C2—C1—H1 | 119.7 | O2—C12—C13 | 115.31 (12) |
C6—C1—H1 | 119.7 | C11—C12—C13 | 120.14 (12) |
C3—C2—C1 | 120.26 (14) | O3—C13—C12 | 119.26 (12) |
C3—C2—H2 | 119.9 | O3—C13—C14 | 121.07 (12) |
C1—C2—H2 | 119.9 | C12—C13—C14 | 119.57 (13) |
C2—C3—C4 | 119.66 (13) | O4—C14—C15 | 124.38 (12) |
C2—C3—H3 | 120.2 | O4—C14—C13 | 115.35 (12) |
C4—C3—H3 | 120.2 | C15—C14—C13 | 120.26 (13) |
C5—C4—C3 | 120.24 (13) | C14—C15—C10 | 119.98 (13) |
C5—C4—H4 | 119.9 | C14—C15—H15 | 120.0 |
C3—C4—H4 | 119.9 | C10—C15—H15 | 120.0 |
C4—C5—C6 | 120.67 (13) | O2—C16—H16A | 109.5 |
C4—C5—H5 | 119.7 | O2—C16—H16B | 109.5 |
C6—C5—H5 | 119.7 | H16A—C16—H16B | 109.5 |
C1—C6—C5 | 118.64 (13) | O2—C16—H16C | 109.5 |
C1—C6—C7 | 123.23 (12) | H16A—C16—H16C | 109.5 |
C5—C6—C7 | 118.13 (12) | H16B—C16—H16C | 109.5 |
O1—C7—C8 | 121.16 (13) | O3—C17—H17A | 109.5 |
O1—C7—C6 | 119.80 (12) | O3—C17—H17B | 109.5 |
C8—C7—C6 | 119.03 (12) | H17A—C17—H17B | 109.5 |
C9—C8—C7 | 121.16 (13) | O3—C17—H17C | 109.5 |
C9—C8—H8 | 119.4 | H17A—C17—H17C | 109.5 |
C7—C8—H8 | 119.4 | H17B—C17—H17C | 109.5 |
C8—C9—C10 | 127.16 (13) | O4—C18—H18A | 109.5 |
C8—C9—H9 | 116.4 | O4—C18—H18B | 109.5 |
C10—C9—H9 | 116.4 | H18A—C18—H18B | 109.5 |
C11—C10—C15 | 119.94 (13) | O4—C18—H18C | 109.5 |
C11—C10—C9 | 118.34 (12) | H18A—C18—H18C | 109.5 |
C15—C10—C9 | 121.72 (12) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | 0.8 (2) | C16—O2—C12—C13 | −175.46 (13) |
C1—C2—C3—C4 | 0.0 (2) | C10—C11—C12—O2 | −177.82 (12) |
C2—C3—C4—C5 | −0.6 (2) | C10—C11—C12—C13 | 1.3 (2) |
C3—C4—C5—C6 | 0.3 (2) | C17—O3—C13—C12 | −112.18 (14) |
C2—C1—C6—C5 | −1.0 (2) | C17—O3—C13—C14 | 71.41 (16) |
C2—C1—C6—C7 | 178.63 (13) | O2—C12—C13—O3 | 1.79 (18) |
C4—C5—C6—C1 | 0.5 (2) | C11—C12—C13—O3 | −177.39 (12) |
C4—C5—C6—C7 | −179.18 (13) | O2—C12—C13—C14 | 178.25 (12) |
C1—C6—C7—O1 | 178.60 (13) | C11—C12—C13—C14 | −0.9 (2) |
C5—C6—C7—O1 | −1.75 (19) | C18—O4—C14—C15 | 2.2 (2) |
C1—C6—C7—C8 | −0.8 (2) | C18—O4—C14—C13 | −178.36 (12) |
C5—C6—C7—C8 | 178.85 (12) | O3—C13—C14—O4 | −2.85 (19) |
O1—C7—C8—C9 | 1.8 (2) | C12—C13—C14—O4 | −179.25 (12) |
C6—C7—C8—C9 | −178.78 (13) | O3—C13—C14—C15 | 176.58 (12) |
C7—C8—C9—C10 | −179.13 (13) | C12—C13—C14—C15 | 0.2 (2) |
C8—C9—C10—C11 | −172.83 (14) | O4—C14—C15—C10 | 179.57 (13) |
C8—C9—C10—C15 | 6.3 (2) | C13—C14—C15—C10 | 0.2 (2) |
C15—C10—C11—C12 | −0.9 (2) | C11—C10—C15—C14 | 0.2 (2) |
C9—C10—C11—C12 | 178.28 (12) | C9—C10—C15—C14 | −178.98 (13) |
C16—O2—C12—C11 | 3.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.95 | 2.56 | 3.248 (2) | 129 |
C9—H9···O1 | 0.95 | 2.46 | 2.805 (2) | 101 |
C17—H17C···O4 | 0.98 | 2.37 | 2.966 (2) | 118 |
C2—H2···Cgii | 0.95 | 2.76 | 3.500 (2) | 135 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z+1/2. |
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