The title compound, C
15H
22O
2, crystallizes in the monoclinic space group
P2
1/
c, with two molecules in the asymmetric unit related by a non-crystallographic inversion centre. The O—H
O hydrogen bonding is exclusively intramolecular.
Supporting information
CCDC reference: 239143
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.053
- wR factor = 0.146
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 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: COLLECT (Nonius, 1998); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVAL14 (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
3,5-di-
tert-butyl-2-hydroxybenzaldehyde
top
Crystal data top
C15H22O2 | F(000) = 1024 |
Mr = 234.33 | Least Squares Treatment of 25 SET4 setting angles. |
Monoclinic, P21/c | Dx = 1.115 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.627 (1) Å | Cell parameters from 56 reflections |
b = 10.1214 (7) Å | θ = 4.0–18.3° |
c = 25.461 (2) Å | µ = 0.07 mm−1 |
β = 111.326 (3)° | T = 150 K |
V = 2791.1 (4) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.10 × 0.10 mm |
Data collection top
Nonius KappaCCD diffractometer | 4178 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.063 |
Graphite monochromator | θmax = 26.5°, θmin = 1.7° |
Detector resolution: 18.4 pixels mm-1 | h = −14→14 |
φ and ω scans | k = −12→12 |
28855 measured reflections | l = −31→31 |
5782 independent reflections | |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0694P)2 + 1.0702P] where P = (Fo2 + 2Fc2)/3 |
5782 reflections | (Δ/σ)max < 0.001 |
358 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
0 constraints | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | Occ. (<1) |
O3 | 0.05469 (11) | 0.58351 (12) | 0.25345 (5) | 0.0400 (4) | |
O4 | 0.14002 (11) | 0.65291 (11) | 0.17592 (5) | 0.0318 (4) | |
C16 | 0.06343 (15) | 0.46869 (17) | 0.23992 (7) | 0.0310 (5) | |
C17 | 0.10307 (14) | 0.42828 (15) | 0.19448 (6) | 0.0242 (5) | |
C18 | 0.10537 (14) | 0.29377 (15) | 0.18269 (6) | 0.0249 (5) | |
C19 | 0.14227 (14) | 0.25093 (14) | 0.13983 (6) | 0.0222 (4) | |
C20 | 0.17529 (14) | 0.34792 (14) | 0.10863 (6) | 0.0218 (4) | |
C21 | 0.17493 (13) | 0.48333 (14) | 0.11826 (6) | 0.0216 (4) | |
C22 | 0.13873 (13) | 0.52287 (14) | 0.16290 (7) | 0.0230 (4) | |
C23 | 0.14686 (15) | 0.10371 (15) | 0.12602 (7) | 0.0269 (5) | |
C24 | 0.2773 (3) | 0.0679 (2) | 0.12946 (15) | 0.0423 (10) | 0.696 (3) |
C25 | 0.1091 (3) | 0.0141 (2) | 0.16444 (12) | 0.0437 (10) | 0.696 (3) |
C26 | 0.0568 (3) | 0.0797 (2) | 0.06482 (11) | 0.0370 (8) | 0.696 (3) |
C27 | 0.21264 (14) | 0.58495 (14) | 0.08260 (7) | 0.0254 (4) | |
C28 | 0.32707 (16) | 0.66135 (17) | 0.12018 (8) | 0.0337 (5) | |
C29 | 0.10537 (17) | 0.68104 (16) | 0.05447 (8) | 0.0356 (5) | |
C30 | 0.24443 (17) | 0.51942 (16) | 0.03554 (7) | 0.0331 (5) | |
C24A | 0.2244 (8) | 0.0309 (6) | 0.1821 (3) | 0.052 (3) | 0.304 (3) |
C25A | 0.0151 (6) | 0.0490 (6) | 0.1072 (3) | 0.045 (2) | 0.304 (3) |
C26A | 0.2021 (8) | 0.0757 (6) | 0.0829 (3) | 0.048 (3) | 0.304 (3) |
O1 | 0.44413 (12) | 0.28484 (12) | 0.24092 (5) | 0.0400 (4) | |
O2 | 0.35678 (11) | 0.21365 (11) | 0.31776 (5) | 0.0320 (4) | |
C1 | 0.43296 (15) | 0.39938 (17) | 0.25400 (7) | 0.0313 (5) | |
C2 | 0.38928 (14) | 0.43908 (15) | 0.29836 (6) | 0.0232 (5) | |
C3 | 0.38316 (14) | 0.57356 (15) | 0.30901 (6) | 0.0240 (5) | |
C4 | 0.34309 (13) | 0.61643 (14) | 0.35105 (6) | 0.0227 (4) | |
C5 | 0.31350 (14) | 0.51900 (15) | 0.38298 (7) | 0.0251 (5) | |
C6 | 0.31904 (14) | 0.38357 (15) | 0.37473 (7) | 0.0248 (5) | |
C7 | 0.35523 (14) | 0.34401 (14) | 0.33018 (6) | 0.0231 (4) | |
C8 | 0.33727 (15) | 0.76439 (15) | 0.36271 (7) | 0.0274 (5) | |
C9 | 0.46935 (18) | 0.81790 (18) | 0.38711 (9) | 0.0453 (6) | |
C10 | 0.2720 (2) | 0.79241 (18) | 0.40363 (9) | 0.0489 (7) | |
C11 | 0.2680 (2) | 0.83824 (17) | 0.30757 (8) | 0.0471 (7) | |
C12 | 0.28823 (16) | 0.28196 (16) | 0.41254 (7) | 0.0319 (5) | |
C13 | 0.39972 (18) | 0.19048 (17) | 0.43969 (8) | 0.0391 (6) | |
C14 | 0.2601 (2) | 0.34849 (19) | 0.46063 (9) | 0.0499 (7) | |
C15 | 0.17470 (18) | 0.20140 (19) | 0.37759 (9) | 0.0464 (7) | |
H20 | 0.1997 | 0.3192 | 0.0787 | 0.026* | |
H24A | 0.3360 | 0.0846 | 0.1677 | 0.063* | 0.696 (3) |
H24B | 0.2994 | 0.1219 | 0.1026 | 0.063* | 0.696 (3) |
H24C | 0.2800 | −0.0258 | 0.1203 | 0.063* | 0.696 (3) |
H4 | 0.112 (2) | 0.656 (2) | 0.2037 (11) | 0.071 (8)* | |
H16 | 0.0427 | 0.4011 | 0.2608 | 0.037* | |
H18 | 0.0812 | 0.2310 | 0.2044 | 0.030* | |
H26A | 0.0583 | −0.0140 | 0.0554 | 0.055* | 0.696 (3) |
H26B | 0.0822 | 0.1333 | 0.0388 | 0.055* | 0.696 (3) |
H26C | −0.0270 | 0.1046 | 0.0615 | 0.055* | 0.696 (3) |
H28A | 0.3961 | 0.5999 | 0.1363 | 0.051* | |
H28B | 0.3090 | 0.7048 | 0.1507 | 0.051* | |
H28C | 0.3491 | 0.7281 | 0.0976 | 0.051* | |
H29A | 0.1302 | 0.7456 | 0.0319 | 0.053* | |
H29B | 0.0842 | 0.7272 | 0.0836 | 0.053* | |
H29C | 0.0334 | 0.6316 | 0.0300 | 0.053* | |
H30A | 0.3138 | 0.4584 | 0.0520 | 0.050* | |
H30B | 0.2674 | 0.5874 | 0.0137 | 0.050* | |
H30C | 0.1725 | 0.4704 | 0.0107 | 0.050* | |
H25A | 0.1154 | −0.0783 | 0.1542 | 0.065* | 0.696 (3) |
H25B | 0.0236 | 0.0334 | 0.1604 | 0.065* | 0.696 (3) |
H25C | 0.1636 | 0.0290 | 0.2036 | 0.065* | 0.696 (3) |
H24D | 0.2206 | −0.0646 | 0.1755 | 0.077* | 0.304 (3) |
H24E | 0.1906 | 0.0515 | 0.2112 | 0.077* | 0.304 (3) |
H24F | 0.3104 | 0.0604 | 0.1946 | 0.077* | 0.304 (3) |
H25D | 0.0159 | −0.0455 | 0.0990 | 0.067* | 0.304 (3) |
H25E | −0.0374 | 0.0957 | 0.0732 | 0.067* | 0.304 (3) |
H25F | −0.0174 | 0.0619 | 0.1373 | 0.067* | 0.304 (3) |
H26D | 0.2849 | 0.1144 | 0.0949 | 0.072* | 0.304 (3) |
H26E | 0.1501 | 0.1144 | 0.0467 | 0.072* | 0.304 (3) |
H26F | 0.2076 | −0.0200 | 0.0786 | 0.072* | 0.304 (3) |
H1 | 0.4545 | 0.4674 | 0.2336 | 0.038* | |
H2 | 0.384 (2) | 0.209 (2) | 0.2897 (10) | 0.054 (6)* | |
H3 | 0.4068 | 0.6365 | 0.2871 | 0.029* | |
H5 | 0.2877 | 0.5474 | 0.4125 | 0.030* | |
H9A | 0.5155 | 0.7707 | 0.4220 | 0.068* | |
H9B | 0.4673 | 0.9124 | 0.3951 | 0.068* | |
H9C | 0.5097 | 0.8049 | 0.3598 | 0.068* | |
H10A | 0.3177 | 0.7508 | 0.4400 | 0.073* | |
H10B | 0.1880 | 0.7564 | 0.3884 | 0.073* | |
H10C | 0.2682 | 0.8881 | 0.4088 | 0.073* | |
H11A | 0.2684 | 0.9332 | 0.3152 | 0.071* | |
H11B | 0.1826 | 0.8066 | 0.2917 | 0.071* | |
H11C | 0.3088 | 0.8221 | 0.2806 | 0.071* | |
H13A | 0.3812 | 0.1280 | 0.4649 | 0.059* | |
H13B | 0.4720 | 0.2435 | 0.4613 | 0.059* | |
H13C | 0.4171 | 0.1417 | 0.4102 | 0.059* | |
H14A | 0.1878 | 0.4060 | 0.4449 | 0.075* | |
H14B | 0.3314 | 0.4013 | 0.4835 | 0.075* | |
H14C | 0.2432 | 0.2807 | 0.4843 | 0.075* | |
H15A | 0.1038 | 0.2606 | 0.3616 | 0.070* | |
H15B | 0.1564 | 0.1359 | 0.4018 | 0.070* | |
H15C | 0.1912 | 0.1562 | 0.3470 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0435 (7) | 0.0401 (7) | 0.0436 (7) | −0.0028 (6) | 0.0246 (6) | −0.0161 (6) |
O4 | 0.0399 (7) | 0.0202 (6) | 0.0405 (7) | −0.0015 (5) | 0.0209 (6) | −0.0074 (5) |
C16 | 0.0277 (9) | 0.0375 (9) | 0.0299 (9) | −0.0026 (7) | 0.0130 (7) | −0.0054 (7) |
C17 | 0.0215 (8) | 0.0274 (8) | 0.0243 (8) | −0.0013 (6) | 0.0092 (6) | −0.0037 (6) |
C18 | 0.0248 (8) | 0.0259 (8) | 0.0247 (8) | −0.0029 (6) | 0.0097 (6) | 0.0018 (6) |
C19 | 0.0226 (7) | 0.0190 (7) | 0.0243 (8) | −0.0004 (6) | 0.0078 (6) | −0.0003 (6) |
C20 | 0.0242 (8) | 0.0206 (7) | 0.0222 (8) | 0.0010 (6) | 0.0103 (6) | −0.0007 (6) |
C21 | 0.0194 (7) | 0.0205 (7) | 0.0243 (8) | 0.0009 (6) | 0.0072 (6) | 0.0011 (6) |
C22 | 0.0199 (8) | 0.0190 (7) | 0.0292 (8) | 0.0006 (6) | 0.0078 (6) | −0.0034 (6) |
C23 | 0.0360 (9) | 0.0172 (7) | 0.0297 (9) | −0.0007 (7) | 0.0147 (7) | 0.0006 (6) |
C24 | 0.0384 (16) | 0.0234 (13) | 0.065 (2) | 0.0067 (11) | 0.0187 (15) | −0.0048 (13) |
C25 | 0.074 (2) | 0.0206 (12) | 0.0456 (17) | −0.0018 (13) | 0.0328 (17) | 0.0045 (11) |
C26 | 0.0477 (16) | 0.0219 (12) | 0.0365 (14) | −0.0040 (11) | 0.0095 (12) | −0.0027 (10) |
C27 | 0.0296 (8) | 0.0182 (7) | 0.0303 (8) | −0.0002 (6) | 0.0132 (7) | 0.0023 (6) |
C28 | 0.0323 (9) | 0.0287 (9) | 0.0429 (10) | −0.0069 (7) | 0.0169 (8) | −0.0009 (7) |
C29 | 0.0396 (10) | 0.0254 (8) | 0.0405 (10) | 0.0053 (7) | 0.0130 (8) | 0.0093 (7) |
C30 | 0.0458 (10) | 0.0257 (8) | 0.0340 (9) | −0.0014 (7) | 0.0220 (8) | 0.0042 (7) |
C24A | 0.079 (6) | 0.023 (3) | 0.041 (4) | 0.017 (3) | 0.008 (4) | 0.003 (3) |
C25A | 0.044 (4) | 0.027 (3) | 0.066 (5) | −0.011 (3) | 0.022 (3) | −0.010 (3) |
C26A | 0.078 (6) | 0.018 (3) | 0.068 (5) | −0.005 (3) | 0.052 (5) | −0.008 (3) |
O1 | 0.0505 (8) | 0.0392 (7) | 0.0365 (7) | 0.0054 (6) | 0.0231 (6) | −0.0096 (6) |
O2 | 0.0412 (7) | 0.0205 (6) | 0.0376 (7) | 0.0023 (5) | 0.0183 (6) | −0.0049 (5) |
C1 | 0.0335 (9) | 0.0347 (9) | 0.0282 (9) | 0.0008 (7) | 0.0142 (7) | −0.0020 (7) |
C2 | 0.0230 (8) | 0.0257 (8) | 0.0212 (8) | 0.0005 (6) | 0.0084 (6) | −0.0019 (6) |
C3 | 0.0244 (8) | 0.0232 (8) | 0.0247 (8) | −0.0010 (6) | 0.0092 (6) | 0.0021 (6) |
C4 | 0.0215 (8) | 0.0213 (7) | 0.0243 (8) | 0.0002 (6) | 0.0071 (6) | −0.0014 (6) |
C5 | 0.0290 (8) | 0.0248 (8) | 0.0248 (8) | 0.0012 (6) | 0.0138 (7) | −0.0018 (6) |
C6 | 0.0252 (8) | 0.0225 (8) | 0.0288 (8) | 0.0015 (6) | 0.0124 (7) | 0.0029 (6) |
C7 | 0.0221 (8) | 0.0193 (7) | 0.0264 (8) | 0.0012 (6) | 0.0070 (6) | −0.0023 (6) |
C8 | 0.0334 (9) | 0.0199 (8) | 0.0304 (9) | −0.0005 (7) | 0.0133 (7) | −0.0023 (6) |
C9 | 0.0451 (11) | 0.0296 (9) | 0.0562 (12) | −0.0053 (8) | 0.0126 (10) | −0.0111 (9) |
C10 | 0.0699 (14) | 0.0272 (9) | 0.0634 (14) | 0.0037 (9) | 0.0408 (12) | −0.0065 (9) |
C11 | 0.0669 (14) | 0.0248 (9) | 0.0432 (11) | 0.0093 (9) | 0.0123 (10) | 0.0020 (8) |
C12 | 0.0407 (10) | 0.0227 (8) | 0.0407 (10) | 0.0044 (7) | 0.0249 (8) | 0.0073 (7) |
C13 | 0.0491 (11) | 0.0328 (9) | 0.0409 (10) | 0.0106 (8) | 0.0230 (9) | 0.0136 (8) |
C14 | 0.0805 (15) | 0.0346 (10) | 0.0578 (13) | 0.0137 (10) | 0.0530 (12) | 0.0146 (9) |
C15 | 0.0413 (11) | 0.0352 (10) | 0.0695 (14) | −0.0030 (8) | 0.0284 (10) | 0.0107 (10) |
Geometric parameters (Å, º) top
O3—C16 | 1.227 (2) | C28—H28A | 0.9797 |
O4—C22 | 1.3560 (18) | C28—H28B | 0.9799 |
O4—H4 | 0.88 (3) | C28—H28C | 0.9796 |
O1—C1 | 1.226 (2) | C29—H29A | 0.9804 |
O2—C7 | 1.3584 (18) | C29—H29B | 0.9807 |
O2—H2 | 0.88 (2) | C29—H29C | 0.9796 |
C16—C17 | 1.451 (2) | C30—H30B | 0.9808 |
C17—C18 | 1.397 (2) | C30—H30C | 0.9802 |
C17—C22 | 1.406 (2) | C30—H30A | 0.9807 |
C18—C19 | 1.380 (2) | C1—C2 | 1.453 (2) |
C19—C20 | 1.401 (2) | C2—C7 | 1.404 (2) |
C19—C23 | 1.536 (2) | C2—C3 | 1.395 (2) |
C20—C21 | 1.393 (2) | C3—C4 | 1.383 (2) |
C21—C22 | 1.406 (2) | C4—C5 | 1.398 (2) |
C21—C27 | 1.538 (2) | C4—C8 | 1.533 (2) |
C23—C24 | 1.531 (4) | C5—C6 | 1.392 (2) |
C23—C25 | 1.512 (3) | C6—C7 | 1.404 (2) |
C23—C26 | 1.548 (3) | C6—C12 | 1.537 (2) |
C23—C24A | 1.568 (7) | C8—C10 | 1.522 (3) |
C23—C26A | 1.487 (9) | C8—C11 | 1.535 (2) |
C23—C25A | 1.533 (8) | C8—C9 | 1.531 (3) |
C27—C29 | 1.538 (2) | C12—C14 | 1.533 (3) |
C27—C30 | 1.528 (2) | C12—C15 | 1.531 (3) |
C27—C28 | 1.536 (3) | C12—C13 | 1.537 (3) |
C16—H16 | 0.9497 | C1—H1 | 0.9493 |
C18—H18 | 0.9493 | C3—H3 | 0.9508 |
C20—H20 | 0.9503 | C5—H5 | 0.9495 |
C24—H24B | 0.9799 | C9—H9A | 0.9791 |
C24—H24A | 0.9793 | C9—H9B | 0.9800 |
C24—H24C | 0.9799 | C9—H9C | 0.9789 |
C24A—H24D | 0.9793 | C10—H10A | 0.9795 |
C24A—H24E | 0.9791 | C10—H10B | 0.9806 |
C24A—H24F | 0.9792 | C10—H10C | 0.9806 |
C25—H25A | 0.9807 | C11—H11A | 0.9802 |
C25—H25C | 0.9792 | C11—H11B | 0.9797 |
C25—H25B | 0.9811 | C11—H11C | 0.9799 |
C25A—H25F | 0.9787 | C13—H13A | 0.9792 |
C25A—H25E | 0.9803 | C13—H13B | 0.9801 |
C25A—H25D | 0.9798 | C13—H13C | 0.9791 |
C26—H26C | 0.9798 | C14—H14A | 0.9803 |
C26—H26B | 0.9812 | C14—H14B | 0.9802 |
C26—H26A | 0.9799 | C14—H14C | 0.9791 |
C26A—H26E | 0.9814 | C15—H15A | 0.9799 |
C26A—H26D | 0.9796 | C15—H15B | 0.9799 |
C26A—H26F | 0.9795 | C15—H15C | 0.9805 |
| | | |
O1···O2 | 2.6122 (18) | H11C···H3 | 2.1720 |
O2···C15 | 3.027 (3) | H13A···H14C | 2.4049 |
O2···O1 | 2.6122 (18) | H13A···H15B | 2.5228 |
O2···C13 | 2.969 (2) | H13B···H14B | 2.4929 |
O3···C4 | 3.387 (2) | H13C···O2 | 2.3154 |
O3···C25i | 3.374 (4) | H13C···C7 | 2.7920 |
O3···O4 | 2.6075 (18) | H13C···H9Bx | 2.4572 |
O4···O3 | 2.6075 (18) | H13C···H15C | 2.5368 |
O4···C29 | 2.983 (2) | H14A···H25Ei | 2.5240 |
O4···C28 | 2.999 (2) | H14A···C25Ai | 2.6727 |
O1···H9Cii | 2.8120 | H14A···H25Di | 2.2746 |
O1···H3ii | 2.5820 | H14A···H5 | 2.1851 |
O1···H24F | 2.7632 | H14A···H15A | 2.4721 |
O1···H2 | 1.80 (2) | H14A···C5 | 2.7578 |
O1···H24A | 2.7311 | H14B···C5 | 2.7614 |
O2···H13C | 2.3154 | H14B···H5 | 2.2460 |
O2···H28Aii | 2.9162 | H14B···H13B | 2.4929 |
O2···H15C | 2.3751 | H14C···H13A | 2.4049 |
O3···H11B | 2.6842 | H14C···H15B | 2.4570 |
O3···H25Bi | 2.7110 | H14C···H26Eiv | 2.4646 |
O3···H18i | 2.6664 | H14C···C26Aiv | 3.0848 |
O3···H4 | 1.79 (2) | H15A···H14A | 2.4721 |
O4···H25Aiii | 2.7702 | H15A···O4v | 2.8578 |
O4···H28B | 2.3379 | H15B···H13A | 2.5228 |
O4···H29B | 2.3243 | H15B···H14C | 2.4570 |
O4···H15Ai | 2.8578 | H15C···O2 | 2.3751 |
C1···C17 | 3.587 (3) | H15C···H13C | 2.5368 |
C1···C22 | 3.588 (2) | H15C···C7 | 2.8334 |
C2···C17 | 3.418 (2) | H16···H18 | 2.3862 |
C2···C16 | 3.544 (3) | H18···H16 | 2.3862 |
C4···O3 | 3.387 (2) | H18···H24E | 2.1882 |
C7···C16 | 3.566 (2) | H18···H25B | 2.2711 |
C13···O2 | 2.969 (2) | H18···C25 | 2.4900 |
C14···C26Aiv | 3.502 (8) | H18···C24A | 2.8078 |
C15···O2 | 3.027 (3) | H18···C25A | 2.9539 |
C16···C7 | 3.566 (2) | H18···H25C | 2.2611 |
C16···C2 | 3.544 (3) | H18···O3v | 2.6664 |
C17···C2 | 3.418 (2) | H18···H25F | 2.3954 |
C17···C1 | 3.587 (3) | H20···C26A | 2.4666 |
C22···C1 | 3.588 (2) | H20···H30C | 2.2453 |
C25···O3v | 3.374 (4) | H20···C24 | 2.8470 |
C26···C26vi | 3.474 (4) | H20···H26D | 2.2696 |
C26A···C14vii | 3.502 (8) | H20···H26E | 2.2252 |
C28···O4 | 2.999 (2) | H20···H24B | 2.2779 |
C29···O4 | 2.983 (2) | H20···H26B | 2.3301 |
C1···H2 | 2.29 (2) | H20···H30A | 2.2052 |
C3···H11C | 2.6728 | H20···C30 | 2.4496 |
C3···H9C | 2.8170 | H20···C26 | 2.8869 |
C5···H10A | 2.7501 | H24A···O1 | 2.7311 |
C5···H14B | 2.7614 | H24A···H25C | 2.5500 |
C5···H14A | 2.7578 | H24B···H20 | 2.2779 |
C5···H10B | 2.8405 | H24B···H26B | 2.4588 |
C7···H13C | 2.7920 | H24B···C20 | 2.7387 |
C7···H15C | 2.8334 | H24C···H26A | 2.5082 |
C9···H3 | 3.0062 | H24C···H25A | 2.4272 |
C9···H30Aviii | 2.8177 | H24D···H25D | 2.4746 |
C10···H30Bix | 3.0734 | H24D···H26F | 2.4581 |
C10···H5 | 2.4908 | H24E···C18 | 2.6455 |
C11···H3 | 2.7671 | H24E···H25F | 2.4678 |
C14···H26Eiv | 2.9356 | H24E···H18 | 2.1882 |
C14···H5 | 2.4380 | H24F···O1 | 2.7632 |
C16···H4 | 2.27 (2) | H24F···H26D | 2.5066 |
C18···H25B | 2.7890 | H25A···H26A | 2.4449 |
C18···H25F | 2.7715 | H25A···H24C | 2.4272 |
C18···H25C | 2.7679 | H25A···O4x | 2.7702 |
C18···H24E | 2.6455 | H25B···H26C | 2.4757 |
C20···H30C | 2.7742 | H25B···C18 | 2.7890 |
C20···H26E | 2.7969 | H25B···H18 | 2.2711 |
C20···H26B | 2.7662 | H25B···O3v | 2.7110 |
C20···H26D | 2.7671 | H25C···H18 | 2.2611 |
C20···H30A | 2.7589 | H25C···H24A | 2.5500 |
C20···H24B | 2.7387 | H25C···C18 | 2.7679 |
C22···H29B | 2.7973 | H25D···H14Av | 2.2746 |
C22···H28B | 2.8024 | H25D···H24D | 2.4746 |
C24···H20 | 2.8470 | H25D···H29Bx | 2.5107 |
C24A···H18 | 2.8078 | H25D···H26F | 2.4791 |
C25···H18 | 2.4900 | H25E···H26E | 2.5126 |
C25A···H14Av | 2.6727 | H25E···H14Av | 2.5240 |
C25A···H18 | 2.9539 | H25F···C18 | 2.7715 |
C26···H20 | 2.8869 | H25F···H18 | 2.3954 |
C26···H26Avi | 2.9365 | H25F···H24E | 2.4678 |
C26A···H20 | 2.4666 | H26A···H25A | 2.4449 |
C26A···H14Cvii | 3.0848 | H26A···H24C | 2.5082 |
C30···H20 | 2.4496 | H26A···C26vi | 2.9365 |
H1···H3 | 2.3753 | H26B···H24B | 2.4588 |
H2···O1 | 1.80 (2) | H26B···C20 | 2.7662 |
H2···C1 | 2.29 (2) | H26B···H20 | 2.3301 |
H3···C11 | 2.7671 | H26C···H25B | 2.4757 |
H3···H1 | 2.3753 | H26D···H20 | 2.2696 |
H3···C9 | 3.0062 | H26D···C20 | 2.7671 |
H3···H9C | 2.4803 | H26D···H24F | 2.5066 |
H3···H11C | 2.1720 | H26E···H25E | 2.5126 |
H3···O1viii | 2.5820 | H26E···C20 | 2.7969 |
H4···O3 | 1.79 (2) | H26E···H20 | 2.2252 |
H4···H11B | 2.5845 | H26E···C14vii | 2.9356 |
H4···C16 | 2.27 (2) | H26E···H14Cvii | 2.4646 |
H5···C10 | 2.4908 | H26F···H24D | 2.4581 |
H5···C14 | 2.4380 | H26F···H25D | 2.4791 |
H5···H10A | 2.1616 | H28A···H30A | 2.4657 |
H5···H14A | 2.1851 | H28A···O2viii | 2.9162 |
H5···H14B | 2.2460 | H28B···O4 | 2.3379 |
H5···H10B | 2.3828 | H28B···H29B | 2.5600 |
H9A···H10A | 2.5112 | H28B···C22 | 2.8024 |
H9B···H30Aviii | 2.4526 | H28C···H29A | 2.4921 |
H9B···H13Ciii | 2.4572 | H28C···H30B | 2.4531 |
H9B···H10C | 2.4755 | H29A···H30B | 2.4209 |
H9B···H11A | 2.4716 | H29A···H28C | 2.4921 |
H9C···H3 | 2.4803 | H29B···H28B | 2.5600 |
H9C···H11C | 2.4752 | H29B···O4 | 2.3243 |
H9C···O1viii | 2.8120 | H29B···C22 | 2.7973 |
H9C···C3 | 2.8170 | H29B···H25Diii | 2.5107 |
H10A···H5 | 2.1616 | H29C···H30Cxi | 2.4630 |
H10A···H9A | 2.5112 | H29C···H30C | 2.4692 |
H10A···C5 | 2.7501 | H30A···C20 | 2.7589 |
H10B···H11B | 2.4923 | H30A···H28A | 2.4657 |
H10B···C5 | 2.8405 | H30A···C9ii | 2.8177 |
H10B···H5 | 2.3828 | H30A···H20 | 2.2052 |
H10C···H11A | 2.4273 | H30A···H9Bii | 2.4526 |
H10C···H9B | 2.4755 | H30B···C10xii | 3.0734 |
H11A···H9B | 2.4716 | H30B···H29A | 2.4209 |
H11A···H10C | 2.4273 | H30B···H28C | 2.4531 |
H11B···H10B | 2.4923 | H30C···C20 | 2.7742 |
H11B···H4 | 2.5845 | H30C···H29Cxi | 2.4630 |
H11B···O3 | 2.6842 | H30C···H20 | 2.2453 |
H11C···H9C | 2.4752 | H30C···H29C | 2.4692 |
H11C···C3 | 2.6728 | | |
| | | |
C22—O4—H4 | 104.9 (13) | H28A—C28—H28B | 109.39 |
C7—O2—H2 | 106.2 (13) | C27—C29—H29B | 109.46 |
O3—C16—C17 | 125.00 (16) | C27—C29—H29C | 109.49 |
C16—C17—C18 | 118.86 (14) | H29A—C29—H29B | 109.52 |
C18—C17—C22 | 120.54 (14) | H29A—C29—H29C | 109.46 |
C16—C17—C22 | 120.61 (14) | H29B—C29—H29C | 109.46 |
C17—C18—C19 | 120.81 (14) | C27—C29—H29A | 109.43 |
C18—C19—C23 | 122.18 (14) | C27—C30—H30C | 109.44 |
C20—C19—C23 | 120.68 (14) | H30B—C30—H30C | 109.49 |
C18—C19—C20 | 117.15 (13) | H30A—C30—H30B | 109.44 |
C19—C20—C21 | 124.79 (14) | H30A—C30—H30C | 109.45 |
C20—C21—C27 | 122.32 (13) | C27—C30—H30B | 109.48 |
C20—C21—C22 | 116.32 (13) | C27—C30—H30A | 109.52 |
C22—C21—C27 | 121.36 (13) | O1—C1—C2 | 125.03 (16) |
O4—C22—C21 | 119.60 (14) | C1—C2—C3 | 118.55 (14) |
C17—C22—C21 | 120.37 (13) | C3—C2—C7 | 120.76 (14) |
O4—C22—C17 | 120.03 (14) | C1—C2—C7 | 120.69 (14) |
C19—C23—C25 | 113.04 (15) | C2—C3—C4 | 120.79 (14) |
C19—C23—C24 | 109.44 (15) | C3—C4—C8 | 120.48 (14) |
C19—C23—C25A | 107.9 (3) | C5—C4—C8 | 122.60 (14) |
C19—C23—C26 | 108.39 (14) | C3—C4—C5 | 116.87 (14) |
C24—C23—C25 | 109.62 (19) | C4—C5—C6 | 124.90 (15) |
C24—C23—C26 | 108.3 (2) | C5—C6—C12 | 122.02 (15) |
C25—C23—C26 | 107.93 (19) | C7—C6—C12 | 121.44 (13) |
C24A—C23—C25A | 107.1 (4) | C5—C6—C7 | 116.53 (14) |
C24A—C23—C26A | 108.9 (4) | O2—C7—C6 | 119.89 (14) |
C25A—C23—C26A | 110.6 (4) | C2—C7—C6 | 120.06 (13) |
C19—C23—C26A | 114.5 (3) | O2—C7—C2 | 120.05 (14) |
C19—C23—C24A | 107.7 (3) | C4—C8—C9 | 108.41 (14) |
C21—C27—C29 | 109.94 (14) | C4—C8—C10 | 112.50 (14) |
C21—C27—C30 | 112.02 (12) | C9—C8—C10 | 109.42 (15) |
C28—C27—C30 | 107.78 (15) | C9—C8—C11 | 108.31 (15) |
C29—C27—C30 | 107.21 (14) | C4—C8—C11 | 110.12 (13) |
C28—C27—C29 | 110.12 (13) | C10—C8—C11 | 108.00 (16) |
C21—C27—C28 | 109.72 (13) | C6—C12—C14 | 111.85 (14) |
O3—C16—H16 | 117.48 | C6—C12—C15 | 109.89 (14) |
C17—C16—H16 | 117.52 | C6—C12—C13 | 109.52 (16) |
C19—C18—H18 | 119.56 | C13—C12—C15 | 110.38 (14) |
C17—C18—H18 | 119.63 | C14—C12—C15 | 107.99 (17) |
C19—C20—H20 | 117.62 | C13—C12—C14 | 107.17 (15) |
C21—C20—H20 | 117.59 | O1—C1—H1 | 117.52 |
C23—C24—H24B | 109.50 | C2—C1—H1 | 117.45 |
C23—C24—H24C | 109.42 | C2—C3—H3 | 119.58 |
C23—C24—H24A | 109.50 | C4—C3—H3 | 119.63 |
H24A—C24—H24C | 109.43 | C4—C5—H5 | 117.52 |
H24B—C24—H24C | 109.54 | C6—C5—H5 | 117.58 |
H24A—C24—H24B | 109.44 | C8—C9—H9A | 109.48 |
C23—C24A—H24E | 109.45 | C8—C9—H9B | 109.45 |
C23—C24A—H24F | 109.49 | C8—C9—H9C | 109.47 |
H24D—C24A—H24F | 109.50 | H9A—C9—H9B | 109.55 |
H24E—C24A—H24F | 109.42 | H9A—C9—H9C | 109.44 |
H24D—C24A—H24E | 109.55 | H9B—C9—H9C | 109.44 |
C23—C24A—H24D | 109.42 | C8—C10—H10A | 109.45 |
H25A—C25—H25C | 109.53 | C8—C10—H10B | 109.44 |
C23—C25—H25B | 109.53 | C8—C10—H10C | 109.51 |
C23—C25—H25A | 109.44 | H10A—C10—H10B | 109.50 |
H25A—C25—H25B | 109.44 | H10A—C10—H10C | 109.46 |
C23—C25—H25C | 109.50 | H10B—C10—H10C | 109.46 |
H25B—C25—H25C | 109.38 | C8—C11—H11A | 109.46 |
C23—C25A—H25F | 109.49 | C8—C11—H11B | 109.51 |
C23—C25A—H25D | 109.48 | C8—C11—H11C | 109.46 |
H25D—C25A—H25E | 109.49 | H11A—C11—H11B | 109.47 |
C23—C25A—H25E | 109.42 | H11A—C11—H11C | 109.50 |
H25E—C25A—H25F | 109.48 | H11B—C11—H11C | 109.44 |
H25D—C25A—H25F | 109.48 | C12—C13—H13A | 109.47 |
H26B—C26—H26C | 109.48 | C12—C13—H13B | 109.47 |
C23—C26—H26B | 109.47 | C12—C13—H13C | 109.53 |
C23—C26—H26C | 109.50 | H13A—C13—H13B | 109.49 |
C23—C26—H26A | 109.42 | H13A—C13—H13C | 109.45 |
H26A—C26—H26C | 109.48 | H13B—C13—H13C | 109.43 |
H26A—C26—H26B | 109.47 | C12—C14—H14A | 109.56 |
H26D—C26A—H26E | 109.46 | C12—C14—H14B | 109.51 |
C23—C26A—H26F | 109.53 | C12—C14—H14C | 109.43 |
C23—C26A—H26D | 109.44 | H14A—C14—H14B | 109.46 |
C23—C26A—H26E | 109.47 | H14A—C14—H14C | 109.47 |
H26D—C26A—H26F | 109.49 | H14B—C14—H14C | 109.40 |
H26E—C26A—H26F | 109.43 | C12—C15—H15A | 109.45 |
C27—C28—H28B | 109.46 | C12—C15—H15B | 109.46 |
H28B—C28—H28C | 109.46 | C12—C15—H15C | 109.50 |
H28A—C28—H28C | 109.54 | H15A—C15—H15B | 109.44 |
C27—C28—H28A | 109.48 | H15A—C15—H15C | 109.47 |
C27—C28—H28C | 109.50 | H15B—C15—H15C | 109.51 |
| | | |
O3—C16—C17—C22 | 1.9 (3) | O1—C1—C2—C3 | 179.07 (17) |
O3—C16—C17—C18 | −178.20 (17) | O1—C1—C2—C7 | −0.3 (3) |
C16—C17—C22—O4 | 2.1 (2) | C7—C2—C3—C4 | −0.2 (2) |
C18—C17—C22—C21 | 1.2 (2) | C1—C2—C7—O2 | −3.4 (2) |
C16—C17—C22—C21 | −178.85 (15) | C3—C2—C7—O2 | 177.25 (15) |
C18—C17—C22—O4 | −177.83 (15) | C3—C2—C7—C6 | −2.5 (2) |
C22—C17—C18—C19 | −0.2 (2) | C1—C2—C7—C6 | 176.84 (16) |
C16—C17—C18—C19 | 179.92 (17) | C1—C2—C3—C4 | −179.52 (15) |
C17—C18—C19—C20 | −0.8 (2) | C2—C3—C4—C8 | 179.68 (15) |
C17—C18—C19—C23 | 179.52 (15) | C2—C3—C4—C5 | 2.0 (2) |
C18—C19—C23—C26 | 118.8 (2) | C8—C4—C5—C6 | −178.97 (16) |
C18—C19—C23—C24 | −123.3 (2) | C3—C4—C5—C6 | −1.4 (3) |
C18—C19—C23—C25 | −0.9 (3) | C3—C4—C8—C11 | 50.3 (2) |
C18—C19—C20—C21 | 0.8 (2) | C3—C4—C8—C9 | −68.05 (19) |
C23—C19—C20—C21 | −179.50 (15) | C3—C4—C8—C10 | 170.80 (16) |
C20—C19—C23—C26 | −60.9 (2) | C5—C4—C8—C11 | −132.23 (18) |
C20—C19—C23—C24 | 57.0 (2) | C5—C4—C8—C10 | −11.7 (2) |
C20—C19—C23—C25 | 179.51 (19) | C5—C4—C8—C9 | 109.44 (18) |
C19—C20—C21—C27 | 179.79 (15) | C4—C5—C6—C12 | 178.40 (16) |
C19—C20—C21—C22 | 0.2 (2) | C4—C5—C6—C7 | −1.1 (3) |
C20—C21—C22—C17 | −1.2 (2) | C12—C6—C7—O2 | 3.8 (2) |
C27—C21—C22—O4 | −1.8 (2) | C5—C6—C7—O2 | −176.69 (15) |
C20—C21—C22—O4 | 177.86 (14) | C5—C6—C7—C2 | 3.0 (2) |
C22—C21—C27—C28 | 62.1 (2) | C5—C6—C12—C14 | −3.5 (2) |
C22—C21—C27—C29 | −59.17 (19) | C5—C6—C12—C15 | 116.39 (18) |
C22—C21—C27—C30 | −178.26 (15) | C7—C6—C12—C13 | 57.3 (2) |
C27—C21—C22—C17 | 179.17 (15) | C7—C6—C12—C14 | 175.98 (17) |
C20—C21—C27—C28 | −117.52 (17) | C7—C6—C12—C15 | −64.1 (2) |
C20—C21—C27—C29 | 121.24 (16) | C12—C6—C7—C2 | −176.51 (15) |
C20—C21—C27—C30 | 2.2 (2) | C5—C6—C12—C13 | −122.20 (18) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+1/2, z+1/2; (v) −x, y−1/2, −z+1/2; (vi) −x, −y, −z; (vii) x, −y+1/2, z−1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) x, −y+3/2, z+1/2; (x) x, y−1, z; (xi) −x, −y+1, −z; (xii) x, −y+3/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.88 (2) | 1.80 (2) | 2.6122 (18) | 151.5 (19) |
O4—H4···O3 | 0.88 (3) | 1.79 (2) | 2.6075 (18) | 153.7 (19) |