The title compound [systematic name: 2-hydroxy-5-methyl-2,4,6-cycloheptatrien-1-one], C
8H
8O
2, has two independent molecules in the asymmetric unit, which are linked into a dimer by a pair of intermolecular O—H
O hydrogen bonds. The crystal packing is consolidated by π–π, C—H
π and C—H
O interactions.
Supporting information
CCDC reference: 636788
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.002 Å
- R factor = 0.039
- wR factor = 0.109
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
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Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et
al., 2002); software used to prepare material for publication: CrystalStructure.
2-hydroxy-5-methyl-2,4,6-cycloheptatrien-1-one
top
Crystal data top
C8H8O2 | F(000) = 576.00 |
Mr = 136.15 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 3212 reflections |
a = 13.628 (3) Å | θ = 3.2–27.5° |
b = 7.1352 (14) Å | µ = 0.10 mm−1 |
c = 14.663 (3) Å | T = 153 K |
β = 110.1031 (11)° | Prism, colourless |
V = 1338.9 (5) Å3 | 0.18 × 0.15 × 0.12 mm |
Z = 8 | |
Data collection top
Rigaku Saturn diffractometer | 2143 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.036 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −17→17 |
Tmin = 0.939, Tmax = 0.988 | k = −8→9 |
10387 measured reflections | l = −18→14 |
3054 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[0.0007Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.25 e Å−3 |
3054 reflections | Δρmin = −0.22 e Å−3 |
203 parameters | |
Special details top
Refinement. Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.70585 (7) | 0.35352 (15) | 0.78154 (7) | 0.0346 (2) | |
O2 | 0.56648 (8) | 0.37165 (15) | 0.60946 (7) | 0.0340 (2) | |
O3 | 0.76150 (7) | 0.36046 (15) | 0.59148 (7) | 0.0353 (2) | |
O4 | 0.87887 (8) | 0.21659 (16) | 0.75555 (7) | 0.0323 (2) | |
C1 | 0.61290 (10) | 0.35616 (18) | 0.77955 (10) | 0.0248 (3) | |
C2 | 0.53141 (10) | 0.36824 (19) | 0.68467 (10) | 0.0253 (3) | |
C3 | 0.42559 (10) | 0.3786 (2) | 0.66276 (10) | 0.0294 (3) | |
C4 | 0.36498 (11) | 0.37736 (19) | 0.72344 (10) | 0.0290 (3) | |
C5 | 0.39403 (11) | 0.36133 (18) | 0.82229 (10) | 0.0266 (3) | |
C6 | 0.49885 (11) | 0.34478 (19) | 0.88568 (10) | 0.0281 (3) | |
C7 | 0.59059 (11) | 0.3442 (2) | 0.86788 (10) | 0.0287 (3) | |
C8 | 0.31104 (12) | 0.3580 (2) | 0.86874 (12) | 0.0369 (4) | |
C9 | 0.84963 (10) | 0.30574 (19) | 0.59327 (9) | 0.0248 (3) | |
C10 | 0.91986 (10) | 0.22804 (19) | 0.68452 (9) | 0.0243 (3) | |
C11 | 1.02070 (11) | 0.16859 (19) | 0.70683 (10) | 0.0273 (3) | |
C12 | 1.08565 (11) | 0.15710 (19) | 0.65003 (10) | 0.0271 (3) | |
C13 | 1.06513 (10) | 0.20409 (19) | 0.55478 (10) | 0.0257 (3) | |
C14 | 0.96811 (10) | 0.27459 (19) | 0.49218 (9) | 0.0261 (3) | |
C15 | 0.87782 (10) | 0.31644 (19) | 0.50797 (9) | 0.0258 (3) | |
C16 | 1.14871 (11) | 0.1775 (2) | 0.51031 (11) | 0.0320 (3) | |
H1 | 0.6419 (17) | 0.372 (3) | 0.6336 (15) | 0.082 (7)* | |
H2 | 0.3865 | 0.3892 | 0.5954 | 0.034* | |
H3 | 0.2918 | 0.3884 | 0.6904 | 0.035* | |
H4 | 0.5065 | 0.3300 | 0.9522 | 0.035* | |
H5 | 0.6512 | 0.3356 | 0.9244 | 0.034* | |
H6 | 0.3291 | 0.4428 | 0.9219 | 0.048* | |
H7 | 0.3058 | 0.2348 | 0.8913 | 0.048* | |
H8 | 0.2458 | 0.3935 | 0.8222 | 0.048* | |
H9 | 0.8106 (17) | 0.265 (3) | 0.7349 (15) | 0.072 (6)* | |
H10 | 1.0525 | 0.1284 | 0.7722 | 0.033* | |
H11 | 1.1538 | 0.1092 | 0.6826 | 0.032* | |
H12 | 0.9656 | 0.2947 | 0.4274 | 0.032* | |
H13 | 0.8232 | 0.3611 | 0.4524 | 0.031* | |
H14 | 1.2052 | 0.1090 | 0.5539 | 0.041* | |
H15 | 1.1207 | 0.1103 | 0.4511 | 0.041* | |
H16 | 1.1729 | 0.2964 | 0.4979 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0226 (5) | 0.0525 (6) | 0.0307 (5) | −0.0012 (4) | 0.0116 (4) | −0.0059 (4) |
O2 | 0.0290 (5) | 0.0529 (6) | 0.0227 (5) | −0.0010 (4) | 0.0121 (4) | 0.0001 (4) |
O3 | 0.0266 (5) | 0.0508 (6) | 0.0308 (5) | 0.0069 (4) | 0.0127 (4) | 0.0052 (4) |
O4 | 0.0316 (5) | 0.0466 (6) | 0.0215 (5) | 0.0039 (4) | 0.0128 (4) | 0.0006 (4) |
C1 | 0.0230 (6) | 0.0262 (6) | 0.0264 (6) | −0.0009 (5) | 0.0101 (5) | −0.0033 (5) |
C2 | 0.0283 (6) | 0.0267 (6) | 0.0243 (6) | −0.0019 (5) | 0.0132 (5) | −0.0012 (5) |
C3 | 0.0243 (6) | 0.0386 (8) | 0.0239 (6) | −0.0014 (6) | 0.0066 (5) | 0.0000 (6) |
C4 | 0.0214 (6) | 0.0345 (7) | 0.0310 (7) | −0.0020 (5) | 0.0089 (5) | −0.0014 (6) |
C5 | 0.0268 (6) | 0.0242 (6) | 0.0329 (7) | −0.0010 (5) | 0.0154 (5) | −0.0019 (5) |
C6 | 0.0329 (7) | 0.0323 (7) | 0.0230 (6) | 0.0018 (6) | 0.0146 (5) | 0.0000 (5) |
C7 | 0.0256 (6) | 0.0372 (7) | 0.0224 (6) | 0.0037 (6) | 0.0070 (5) | −0.0020 (5) |
C8 | 0.0331 (7) | 0.0455 (9) | 0.0391 (8) | −0.0010 (7) | 0.0216 (6) | −0.0031 (7) |
C9 | 0.0238 (6) | 0.0270 (6) | 0.0240 (6) | −0.0025 (5) | 0.0088 (5) | −0.0018 (5) |
C10 | 0.0281 (6) | 0.0257 (6) | 0.0204 (6) | −0.0023 (5) | 0.0102 (5) | −0.0034 (5) |
C11 | 0.0299 (7) | 0.0326 (7) | 0.0195 (6) | 0.0029 (6) | 0.0084 (5) | 0.0019 (5) |
C12 | 0.0249 (6) | 0.0277 (7) | 0.0279 (7) | 0.0016 (5) | 0.0079 (5) | −0.0015 (5) |
C13 | 0.0281 (6) | 0.0223 (6) | 0.0287 (6) | −0.0038 (5) | 0.0126 (5) | −0.0054 (5) |
C14 | 0.0303 (7) | 0.0284 (6) | 0.0210 (6) | −0.0051 (5) | 0.0105 (5) | −0.0026 (5) |
C15 | 0.0257 (6) | 0.0292 (7) | 0.0208 (6) | −0.0032 (5) | 0.0060 (5) | 0.0003 (5) |
C16 | 0.0321 (7) | 0.0333 (7) | 0.0366 (7) | −0.0027 (6) | 0.0196 (6) | −0.0049 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2571 (17) | C13—C16 | 1.506 (2) |
O2—C2 | 1.344 (2) | C14—C15 | 1.361 (2) |
O3—C9 | 1.2545 (17) | O2—H1 | 0.97 (2) |
O4—C10 | 1.3429 (19) | O4—H9 | 0.94 (2) |
C1—C2 | 1.4540 (16) | C3—H2 | 0.950 |
C1—C7 | 1.431 (2) | C4—H3 | 0.950 |
C2—C3 | 1.3674 (18) | C6—H4 | 0.950 |
C3—C4 | 1.407 (2) | C7—H5 | 0.950 |
C4—C5 | 1.370 (2) | C8—H6 | 0.950 |
C5—C6 | 1.4162 (17) | C8—H7 | 0.950 |
C5—C8 | 1.508 (2) | C8—H8 | 0.950 |
C6—C7 | 1.362 (2) | C11—H10 | 0.950 |
C9—C10 | 1.4606 (16) | C12—H11 | 0.950 |
C9—C15 | 1.431 (2) | C14—H12 | 0.950 |
C10—C11 | 1.3662 (19) | C15—H13 | 0.950 |
C11—C12 | 1.411 (2) | C16—H14 | 0.950 |
C12—C13 | 1.368 (2) | C16—H15 | 0.950 |
C13—C14 | 1.4175 (16) | C16—H16 | 0.950 |
| | | |
O1···O3 | 3.1299 (15) | H3···C13xii | 3.317 |
O1···O4 | 2.6976 (15) | H3···C16xii | 3.082 |
O1···C4i | 3.5258 (17) | H3···H9v | 3.382 |
O1···C12ii | 3.4369 (16) | H3···H11xii | 2.716 |
O1···C15iii | 3.5549 (14) | H3···H13iv | 2.789 |
O2···O2iv | 3.5977 (13) | H3···H14xii | 2.784 |
O2···O3 | 2.7606 (15) | H3···H16xii | 2.806 |
O2···C6v | 3.4983 (17) | H4···O2i | 3.447 |
O2···C6vi | 3.4528 (17) | H4···O2iii | 2.600 |
O3···O1 | 3.1299 (15) | H4···C2iii | 3.598 |
O3···O2 | 2.7606 (15) | H4···C6xiii | 3.341 |
O4···O1 | 2.6976 (15) | H4···H1iii | 3.030 |
O4···C11ii | 3.4727 (17) | H4···H2iii | 3.450 |
O4···C12ii | 3.4014 (17) | H4···H4xiii | 2.838 |
O4···C14iii | 3.2589 (15) | H4···H6xiii | 2.866 |
C1···C3i | 3.5923 (19) | H5···O3iii | 2.772 |
C1···C4i | 3.4312 (18) | H5···C3i | 3.527 |
C2···C6v | 3.5360 (19) | H5···C9iii | 3.139 |
C3···C1v | 3.5923 (19) | H5···C15iii | 3.100 |
C3···C7v | 3.349 (2) | H5···C16ii | 3.537 |
C4···O1v | 3.5258 (17) | H5···H1iii | 3.448 |
C4···C1v | 3.4312 (18) | H5···H2i | 3.223 |
C6···O2i | 3.4983 (17) | H5···H6xiii | 2.690 |
C6···O2iii | 3.4528 (17) | H5···H13iii | 2.640 |
C6···C2i | 3.5360 (19) | H5···H14ii | 2.703 |
C7···C3i | 3.349 (2) | H5···H15ii | 3.597 |
C8···C16vii | 3.525 (2) | H6···O2v | 3.471 |
C10···C11ii | 3.4911 (18) | H6···O3v | 3.206 |
C11···O4viii | 3.4727 (17) | H6···C6xiii | 3.348 |
C11···C10viii | 3.4911 (18) | H6···C7xiii | 3.270 |
C12···O1viii | 3.4369 (16) | H6···C9v | 3.509 |
C12···O4viii | 3.4014 (17) | H6···C16vii | 3.263 |
C13···C13ix | 3.5005 (18) | H6···H1v | 3.227 |
C13···C14ix | 3.4829 (19) | H6···H2iii | 3.366 |
C14···O4vi | 3.2589 (15) | H6···H4xiii | 2.866 |
C14···C13ix | 3.4829 (19) | H6···H5xiii | 2.690 |
C14···C14x | 3.3194 (19) | H6···H9v | 3.346 |
C14···C15x | 3.5954 (19) | H6···H14vii | 2.996 |
C14···C16ix | 3.592 (2) | H6···H15vii | 3.038 |
C15···O1vi | 3.5549 (14) | H6···H16vii | 3.211 |
C15···C14x | 3.5954 (19) | H7···O2i | 3.123 |
C15···C16ix | 3.544 (2) | H7···O3i | 2.864 |
C16···C8xi | 3.525 (2) | H7···C16vii | 3.255 |
C16···C14ix | 3.592 (2) | H7···H1i | 2.743 |
C16···C15ix | 3.544 (2) | H7···H2iii | 2.948 |
O1···H3i | 3.343 | H7···H10xii | 3.377 |
O1···H9 | 1.89 (2) | H7···H11xii | 3.178 |
O1···H11ii | 2.563 | H7···H14vii | 3.325 |
O1···H13iii | 2.902 | H7···H15vii | 3.143 |
O1···H14ii | 2.933 | H7···H16vii | 2.779 |
O2···H4v | 3.447 | H8···O3v | 3.577 |
O2···H4vi | 2.600 | H8···O4v | 2.858 |
O2···H6i | 3.471 | H8···C10v | 3.264 |
O2···H7v | 3.123 | H8···C11xii | 3.359 |
O2···H9 | 3.29 (2) | H8···C12xii | 3.193 |
O3···H1 | 1.93 (2) | H8···C16vii | 3.482 |
O3···H2iv | 3.312 | H8···H9v | 2.809 |
O3···H5vi | 2.772 | H8···H10xii | 3.120 |
O3···H6i | 3.206 | H8···H11xii | 2.849 |
O3···H7v | 2.864 | H8···H15vii | 2.949 |
O3···H8i | 3.577 | H8···H16vii | 3.349 |
O3···H10ii | 3.255 | H9···O1 | 1.89 (2) |
O3···H11ii | 3.581 | H9···O2 | 3.29 (2) |
O3···H16x | 3.053 | H9···C1 | 3.05 (2) |
O4···H1 | 3.30 (2) | H9···C8i | 3.43 (2) |
O4···H3i | 3.576 | H9···C11ii | 3.60 (2) |
O4···H8i | 2.858 | H9···C12ii | 3.32 (2) |
O4···H10ii | 3.152 | H9···H1 | 2.39 (2) |
O4···H11ii | 3.024 | H9···H3i | 3.382 |
O4···H12iii | 2.388 | H9···H6i | 3.346 |
O4···H13iii | 3.274 | H9···H8i | 2.809 |
C1···H3i | 3.553 | H9···H10ii | 3.215 |
C1···H9 | 3.05 (2) | H9···H11ii | 2.705 |
C1···H11ii | 3.530 | H9···H12iii | 2.917 |
C1···H13iii | 3.471 | H9···H13iii | 3.262 |
C1···H14ii | 3.347 | H10···O3viii | 3.255 |
C2···H4vi | 3.598 | H10···O4viii | 3.152 |
C3···H5v | 3.527 | H10···C9viii | 3.027 |
C3···H14xii | 3.460 | H10···C10viii | 2.923 |
C3···H16xii | 3.510 | H10···C11viii | 3.473 |
C4···H11xii | 3.335 | H10···C16iii | 3.561 |
C4···H13iv | 3.487 | H10···H7xiv | 3.377 |
C4···H14xii | 3.297 | H10···H8xiv | 3.120 |
C4···H16xii | 3.488 | H10···H9viii | 3.215 |
C6···H2i | 3.576 | H10···H12iii | 2.955 |
C6···H4xiii | 3.341 | H10···H15iii | 3.090 |
C6···H6xiii | 3.348 | H10···H16iii | 3.195 |
C7···H2i | 3.288 | H11···O1viii | 2.563 |
C7···H6xiii | 3.270 | H11···O3viii | 3.581 |
C7···H13iii | 3.321 | H11···O4viii | 3.024 |
C7···H14ii | 3.230 | H11···C1viii | 3.530 |
C8···H1i | 3.53 (2) | H11···C4xiv | 3.335 |
C8···H2iii | 3.587 | H11···C8xiv | 3.343 |
C8···H9v | 3.43 (2) | H11···H1viii | 3.567 |
C8···H11xii | 3.343 | H11···H3xiv | 2.716 |
C8···H14vii | 3.492 | H11···H7xiv | 3.178 |
C8···H15vii | 3.224 | H11···H8xiv | 2.849 |
C8···H16vii | 3.285 | H11···H9viii | 2.705 |
C9···H1 | 3.12 (2) | H11···H12ix | 3.427 |
C9···H5vi | 3.139 | H12···O4vi | 2.388 |
C9···H6i | 3.509 | H12···C10vi | 3.401 |
C9···H10ii | 3.027 | H12···C11vi | 3.572 |
C9···H14ix | 3.586 | H12···C12ix | 3.409 |
C9···H15ix | 3.095 | H12···C14x | 3.304 |
C9···H16x | 3.108 | H12···C15x | 3.429 |
C10···H8i | 3.264 | H12···H9vi | 2.917 |
C10···H10ii | 2.923 | H12···H10vi | 2.955 |
C10···H12iii | 3.401 | H12···H11ix | 3.427 |
C10···H15ix | 3.054 | H12···H12x | 3.553 |
C11···H8xiv | 3.359 | H13···O1vi | 2.902 |
C11···H9viii | 3.60 (2) | H13···O4vi | 3.274 |
C11···H10ii | 3.473 | H13···C1vi | 3.471 |
C11···H12iii | 3.572 | H13···C4iv | 3.487 |
C11···H15ix | 3.157 | H13···C7vi | 3.321 |
C12···H3xiv | 3.135 | H13···C13x | 3.473 |
C12···H8xiv | 3.193 | H13···C16x | 3.338 |
C12···H9viii | 3.32 (2) | H13···H2iv | 3.233 |
C12···H12ix | 3.409 | H13···H3iv | 2.789 |
C12···H15ix | 3.298 | H13···H5vi | 2.640 |
C13···H3xiv | 3.317 | H13···H9vi | 3.262 |
C13···H13x | 3.473 | H13···H14ix | 3.374 |
C13···H15ix | 3.362 | H13···H16x | 2.546 |
C14···H12x | 3.304 | H14···O1viii | 2.933 |
C14···H14ix | 3.525 | H14···C1viii | 3.347 |
C14···H15ix | 3.223 | H14···C3xiv | 3.460 |
C15···H5vi | 3.100 | H14···C4xiv | 3.297 |
C15···H12x | 3.429 | H14···C7viii | 3.230 |
C15···H14ix | 3.257 | H14···C8xi | 3.492 |
C15···H15ix | 3.102 | H14···C9ix | 3.586 |
C15···H16x | 2.842 | H14···C14ix | 3.525 |
C16···H2xiv | 3.400 | H14···C15ix | 3.257 |
C16···H3xiv | 3.082 | H14···H2xiv | 3.072 |
C16···H5viii | 3.537 | H14···H3xiv | 2.784 |
C16···H6xi | 3.263 | H14···H5viii | 2.703 |
C16···H7xi | 3.255 | H14···H6xi | 2.996 |
C16···H8xi | 3.482 | H14···H7xi | 3.325 |
C16···H10vi | 3.561 | H14···H13ix | 3.374 |
C16···H13x | 3.338 | H15···C8xi | 3.224 |
H1···O3 | 1.93 (2) | H15···C9ix | 3.095 |
H1···O4 | 3.30 (2) | H15···C10ix | 3.054 |
H1···C8v | 3.53 (2) | H15···C11ix | 3.157 |
H1···C9 | 3.12 (2) | H15···C12ix | 3.298 |
H1···H4vi | 3.030 | H15···C13ix | 3.362 |
H1···H5vi | 3.448 | H15···C14ix | 3.223 |
H1···H6i | 3.227 | H15···C15ix | 3.102 |
H1···H7v | 2.743 | H15···H5viii | 3.597 |
H1···H9 | 2.39 (2) | H15···H6xi | 3.038 |
H1···H11ii | 3.567 | H15···H7xi | 3.143 |
H2···O3iv | 3.312 | H15···H8xi | 2.949 |
H2···C6v | 3.576 | H15···H10vi | 3.090 |
H2···C7v | 3.288 | H16···O3x | 3.053 |
H2···C8vi | 3.587 | H16···C3xiv | 3.510 |
H2···C16xii | 3.400 | H16···C4xiv | 3.488 |
H2···H4vi | 3.450 | H16···C8xi | 3.285 |
H2···H5v | 3.223 | H16···C9x | 3.108 |
H2···H6vi | 3.366 | H16···C15x | 2.842 |
H2···H7vi | 2.948 | H16···H2xiv | 2.844 |
H2···H13iv | 3.233 | H16···H3xiv | 2.806 |
H2···H14xii | 3.072 | H16···H6xi | 3.211 |
H2···H16xii | 2.844 | H16···H7xi | 2.779 |
H3···O1v | 3.343 | H16···H8xi | 3.349 |
H3···O4v | 3.576 | H16···H10vi | 3.195 |
H3···C1v | 3.553 | H16···H13x | 2.546 |
H3···C12xii | 3.135 | | |
| | | |
O1—C1—C2 | 117.08 (13) | C2—C3—H2 | 114.7 |
O1—C1—C7 | 120.26 (11) | C4—C3—H2 | 114.6 |
C2—C1—C7 | 122.65 (12) | C3—C4—H3 | 114.7 |
O2—C2—C1 | 114.58 (12) | C5—C4—H3 | 114.7 |
O2—C2—C3 | 116.73 (11) | C5—C6—H4 | 114.4 |
C1—C2—C3 | 128.68 (14) | C7—C6—H4 | 114.3 |
C2—C3—C4 | 130.70 (12) | C1—C7—H5 | 113.7 |
C3—C4—C5 | 130.60 (12) | C6—C7—H5 | 114.4 |
C4—C5—C6 | 124.12 (15) | C5—C8—H6 | 109.7 |
C4—C5—C8 | 119.37 (12) | C5—C8—H7 | 109.2 |
C6—C5—C8 | 116.50 (12) | C5—C8—H8 | 109.5 |
C5—C6—C7 | 131.27 (14) | H6—C8—H7 | 109.5 |
C1—C7—C6 | 131.89 (11) | H6—C8—H8 | 109.5 |
O3—C9—C10 | 117.29 (13) | H7—C8—H8 | 109.5 |
O3—C9—C15 | 120.51 (10) | C10—C11—H10 | 114.0 |
C10—C9—C15 | 122.18 (12) | C12—C11—H10 | 114.6 |
O4—C10—C9 | 114.66 (11) | C11—C12—H11 | 115.3 |
O4—C10—C11 | 116.60 (11) | C13—C12—H11 | 115.0 |
C9—C10—C11 | 128.73 (14) | C13—C14—H12 | 114.0 |
C10—C11—C12 | 131.32 (12) | C15—C14—H12 | 114.4 |
C11—C12—C13 | 129.69 (12) | C9—C15—H13 | 113.6 |
C12—C13—C14 | 124.45 (14) | C14—C15—H13 | 114.5 |
C12—C13—C16 | 119.42 (11) | C13—C16—H14 | 109.4 |
C14—C13—C16 | 116.11 (12) | C13—C16—H15 | 109.5 |
C13—C14—C15 | 131.62 (13) | C13—C16—H16 | 109.5 |
C9—C15—C14 | 131.83 (10) | H14—C16—H15 | 109.5 |
C2—O2—H1 | 109.4 (14) | H14—C16—H16 | 109.5 |
C10—O4—H9 | 110.9 (14) | H15—C16—H16 | 109.5 |
| | | |
O1—C1—C2—O2 | 1.19 (17) | O3—C9—C10—O4 | 2.94 (17) |
O1—C1—C2—C3 | −177.96 (13) | O3—C9—C10—C11 | −176.20 (13) |
O1—C1—C7—C6 | 179.68 (14) | O3—C9—C15—C14 | 176.88 (14) |
C2—C1—C7—C6 | −1.5 (2) | C10—C9—C15—C14 | −4.5 (2) |
C7—C1—C2—O2 | −177.69 (12) | C15—C9—C10—O4 | −175.71 (12) |
C7—C1—C2—C3 | 3.2 (2) | C15—C9—C10—C11 | 5.2 (2) |
O2—C2—C3—C4 | 179.56 (13) | O4—C10—C11—C12 | 178.27 (13) |
C1—C2—C3—C4 | −1.3 (2) | C9—C10—C11—C12 | −2.6 (2) |
C2—C3—C4—C5 | −1.6 (2) | C10—C11—C12—C13 | 0.3 (2) |
C3—C4—C5—C6 | 1.1 (2) | C11—C12—C13—C14 | −1.0 (2) |
C3—C4—C5—C8 | −178.03 (14) | C11—C12—C13—C16 | −179.76 (13) |
C4—C5—C6—C7 | 1.4 (2) | C12—C13—C14—C15 | 2.0 (2) |
C8—C5—C6—C7 | −179.44 (14) | C16—C13—C14—C15 | −179.27 (14) |
C5—C6—C7—C1 | −1.4 (2) | C13—C14—C15—C9 | 0.7 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+3/2; (vi) x, −y+1/2, z−1/2; (vii) x−1, −y+1/2, z+1/2; (viii) −x+2, y−1/2, −z+3/2; (ix) −x+2, −y, −z+1; (x) −x+2, −y+1, −z+1; (xi) x+1, −y+1/2, z−1/2; (xii) x−1, y, z; (xiii) −x+1, −y+1, −z+2; (xiv) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 0.97 (2) | 2.04 (2) | 2.5877 (12) | 113.7 (19) |
O2—H1···O3 | 0.97 (2) | 1.93 (2) | 2.7606 (15) | 142.3 (19) |
O4—H9···O1 | 0.94 (2) | 1.89 (2) | 2.6976 (15) | 142.4 (19) |
O4—H9···O3 | 0.94 (2) | 2.09 (2) | 2.5989 (12) | 112.6 (19) |
C6—H4···O2iii | 0.95 | 2.60 | 3.4528 (17) | 150 |
C12—H11···O1viii | 0.95 | 2.56 | 3.4369 (16) | 153 |
C14—H12···O4vi | 0.95 | 2.39 | 3.2589 (15) | 152 |
Symmetry codes: (iii) x, −y+1/2, z+1/2; (vi) x, −y+1/2, z−1/2; (viii) −x+2, y−1/2, −z+3/2. |