The title compound, C
15H
16O
3, has two molecules in the asymmetric unit. The cyclohex-2-enone ring has an envelope conformation in both molecules. The crystal exhibits twinning. The molecular packing in the crystal structure is determined by weak intermolecular C—H

O interactions.
Supporting information
CCDC reference: 613756
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.122
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C14 .. 6.26 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C29 .. 5.14 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C29
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
5 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
(
R,
S)-5-Carboxymethyl-5-phenyl-3-methylcyclohex-2-enone
top
Crystal data top
C15H16O3 | Z = 4 |
Mr = 244.29 | F(000) = 520.00 |
Triclinic, P1 | Dx = 1.247 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 9.317 (4) Å | Cell parameters from 9544 reflections |
b = 12.332 (5) Å | θ = 3.3–27.5° |
c = 12.734 (5) Å | µ = 0.09 mm−1 |
α = 67.495 (16)° | T = 298 K |
β = 84.826 (16)° | Block, colourless |
γ = 74.278 (16)° | 0.27 × 0.26 × 0.17 mm |
V = 1300.9 (9) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.023 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −12→12 |
12919 measured reflections | k = −15→15 |
5900 independent reflections | l = −14→16 |
3491 reflections with F2 > 2.0σ(F2) | |
Refinement top
Refinement on F2 | w = 1/[0.0008Fo2 + 1.0000σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max < 0.001 |
wR(F2) = 0.122 | Δρmax = 0.22 e Å−3 |
S = 1.02 | Δρmin = −0.15 e Å−3 |
5900 reflections | Extinction correction: Larson (1970) Crystallographic Computing eq. 22 |
336 parameters | Extinction coefficient: 66 (15) |
H-atom parameters constrained | |
Special details top
Geometry. The crystal is a twin. It has a chiral centre at the position 5 of the
cyclohex-2-enone ring. |
Refinement. Refinement 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 | 0.56135 (14) | 0.83556 (11) | 0.81733 (12) | 0.0776 (4) | |
O2 | 0.20420 (14) | 0.77551 (12) | 0.89822 (10) | 0.0824 (4) | |
O3 | 0.04497 (12) | 0.79912 (11) | 0.76893 (10) | 0.0634 (3) | |
O4 | 0.47407 (14) | 0.22112 (12) | 0.60890 (11) | 0.0744 (4) | |
O5 | 0.86986 (13) | 0.23755 (12) | 0.59558 (10) | 0.0812 (4) | |
O6 | 0.98248 (12) | 0.18918 (10) | 0.75794 (9) | 0.0604 (3) | |
C1 | 0.29760 (14) | 0.70313 (12) | 0.74777 (11) | 0.0377 (3) | |
C2 | 0.27651 (14) | 0.57566 (12) | 0.77622 (12) | 0.0409 (3) | |
C3 | 0.22295 (17) | 0.54393 (12) | 0.69685 (12) | 0.0475 (4) | |
C4 | 0.20191 (19) | 0.42869 (14) | 0.72653 (16) | 0.0595 (5) | |
C5 | 0.2357 (2) | 0.34468 (14) | 0.83414 (17) | 0.0658 (5) | |
C6 | 0.2890 (2) | 0.37448 (16) | 0.91324 (16) | 0.0681 (5) | |
C7 | 0.3085 (2) | 0.48899 (13) | 0.88477 (12) | 0.0574 (5) | |
C8 | 0.45087 (17) | 0.69681 (12) | 0.78720 (13) | 0.0514 (4) | |
C9 | 0.47753 (18) | 0.81977 (13) | 0.75878 (14) | 0.0536 (4) | |
C10 | 0.40459 (18) | 0.91716 (13) | 0.65692 (13) | 0.0525 (4) | |
C11 | 0.31618 (17) | 0.90070 (12) | 0.59109 (12) | 0.0476 (4) | |
C12 | 0.28085 (18) | 0.78065 (12) | 0.62072 (12) | 0.0462 (4) | |
C13 | 0.2476 (2) | 0.99865 (14) | 0.48327 (13) | 0.0695 (5) | |
C14 | 0.17923 (16) | 0.76294 (12) | 0.81404 (11) | 0.0420 (4) | |
C15 | −0.0752 (2) | 0.8486 (2) | 0.8312 (2) | 0.0875 (7) | |
C16 | 0.73419 (16) | 0.31345 (12) | 0.73434 (11) | 0.0400 (3) | |
C17 | 0.76983 (16) | 0.43231 (12) | 0.72063 (12) | 0.0440 (4) | |
C18 | 0.81498 (17) | 0.45133 (13) | 0.81127 (13) | 0.0514 (4) | |
C19 | 0.84956 (19) | 0.55841 (16) | 0.79571 (17) | 0.0624 (5) | |
C20 | 0.8394 (2) | 0.64751 (16) | 0.69083 (18) | 0.0675 (5) | |
C21 | 0.7930 (2) | 0.63127 (18) | 0.60140 (18) | 0.0886 (7) | |
C22 | 0.7588 (2) | 0.52464 (17) | 0.61592 (14) | 0.0775 (6) | |
C23 | 0.59465 (17) | 0.33725 (13) | 0.66544 (12) | 0.0490 (4) | |
C24 | 0.54867 (18) | 0.22373 (14) | 0.68188 (13) | 0.0508 (4) | |
C25 | 0.59101 (18) | 0.12138 (13) | 0.78781 (12) | 0.0528 (4) | |
C26 | 0.66125 (18) | 0.12660 (12) | 0.87171 (12) | 0.0486 (4) | |
C27 | 0.70954 (18) | 0.23752 (12) | 0.85852 (12) | 0.0469 (4) | |
C28 | 0.6949 (2) | 0.02476 (14) | 0.98382 (13) | 0.0692 (5) | |
C29 | 0.86691 (16) | 0.24303 (12) | 0.68704 (12) | 0.0424 (4) | |
C30 | 1.1155 (2) | 0.12498 (18) | 0.71811 (16) | 0.0750 (6) | |
H3 | 0.2009 | 0.6003 | 0.6231 | 0.057* | |
H4 | 0.1647 | 0.4086 | 0.6730 | 0.071* | |
H5 | 0.2225 | 0.2673 | 0.8536 | 0.079* | |
H6 | 0.3121 | 0.3172 | 0.9865 | 0.082* | |
H7 | 0.3439 | 0.5084 | 0.9395 | 0.069* | |
H10 | 0.4203 | 0.9938 | 0.6370 | 0.063* | |
H18 | 0.8221 | 0.3912 | 0.8836 | 0.062* | |
H19 | 0.8801 | 0.5696 | 0.8576 | 0.075* | |
H20 | 0.8641 | 0.7191 | 0.6805 | 0.081* | |
H21 | 0.7842 | 0.6926 | 0.5296 | 0.106* | |
H22 | 0.7275 | 0.5150 | 0.5535 | 0.093* | |
H25 | 0.5683 | 0.0491 | 0.7978 | 0.063* | |
H81 | 0.4590 | 0.6540 | 0.8690 | 0.062* | |
H82 | 0.5267 | 0.6522 | 0.7509 | 0.062* | |
H121 | 0.1788 | 0.7956 | 0.5973 | 0.055* | |
H122 | 0.3479 | 0.7360 | 0.5797 | 0.055* | |
H131 | 0.2742 | 0.9708 | 0.4216 | 0.083* | |
H132 | 0.2833 | 1.0691 | 0.4687 | 0.083* | |
H133 | 0.1411 | 1.0192 | 0.4901 | 0.083* | |
H151 | −0.0590 | 0.8024 | 0.9112 | 0.105* | |
H152 | −0.1682 | 0.8443 | 0.8082 | 0.105* | |
H153 | −0.0780 | 0.9317 | 0.8155 | 0.105* | |
H231 | 0.6144 | 0.3762 | 0.5855 | 0.059* | |
H232 | 0.5130 | 0.3913 | 0.6882 | 0.059* | |
H271 | 0.8022 | 0.2122 | 0.9007 | 0.056* | |
H272 | 0.6332 | 0.2876 | 0.8895 | 0.056* | |
H281 | 0.7998 | 0.0026 | 1.0003 | 0.083* | |
H282 | 0.6668 | −0.0438 | 0.9818 | 0.083* | |
H283 | 0.6399 | 0.0497 | 1.0418 | 0.083* | |
H301 | 1.0888 | 0.0789 | 0.6804 | 0.090* | |
H302 | 1.1806 | 0.0710 | 0.7816 | 0.090* | |
H303 | 1.1655 | 0.1823 | 0.6659 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0721 (8) | 0.0675 (8) | 0.1041 (10) | −0.0249 (6) | −0.0267 (7) | −0.0330 (7) |
O2 | 0.0799 (9) | 0.1225 (11) | 0.0564 (7) | −0.0104 (8) | −0.0045 (6) | −0.0554 (8) |
O3 | 0.0399 (6) | 0.0862 (8) | 0.0786 (8) | −0.0071 (5) | 0.0000 (5) | −0.0524 (7) |
O4 | 0.0795 (9) | 0.0811 (8) | 0.0747 (8) | −0.0286 (7) | −0.0189 (6) | −0.0325 (7) |
O5 | 0.0715 (8) | 0.1235 (11) | 0.0515 (7) | 0.0004 (7) | −0.0036 (5) | −0.0522 (7) |
O6 | 0.0539 (6) | 0.0713 (7) | 0.0514 (6) | 0.0056 (5) | −0.0088 (5) | −0.0305 (5) |
C1 | 0.0397 (7) | 0.0364 (7) | 0.0381 (7) | −0.0108 (5) | 0.0002 (5) | −0.0142 (6) |
C2 | 0.0385 (7) | 0.0390 (7) | 0.0451 (8) | −0.0102 (6) | 0.0041 (6) | −0.0162 (6) |
C3 | 0.0487 (8) | 0.0449 (8) | 0.0502 (8) | −0.0132 (6) | 0.0003 (7) | −0.0182 (7) |
C4 | 0.0603 (10) | 0.0516 (9) | 0.0786 (12) | −0.0205 (8) | 0.0035 (9) | −0.0338 (9) |
C5 | 0.0684 (11) | 0.0425 (9) | 0.0863 (13) | −0.0221 (8) | 0.0109 (10) | −0.0207 (9) |
C6 | 0.0797 (13) | 0.0483 (9) | 0.0628 (11) | −0.0205 (9) | −0.0008 (9) | −0.0032 (8) |
C7 | 0.0691 (11) | 0.0509 (9) | 0.0496 (9) | −0.0206 (8) | −0.0035 (8) | −0.0114 (7) |
C8 | 0.0432 (8) | 0.0446 (8) | 0.0655 (10) | −0.0110 (7) | −0.0067 (7) | −0.0183 (7) |
C9 | 0.0420 (8) | 0.0507 (9) | 0.0731 (11) | −0.0127 (7) | −0.0017 (7) | −0.0276 (8) |
C10 | 0.0509 (9) | 0.0432 (8) | 0.0672 (10) | −0.0180 (7) | 0.0092 (7) | −0.0226 (8) |
C11 | 0.0522 (9) | 0.0417 (8) | 0.0464 (8) | −0.0137 (6) | 0.0109 (7) | −0.0149 (7) |
C12 | 0.0560 (9) | 0.0474 (8) | 0.0390 (7) | −0.0181 (7) | 0.0059 (6) | −0.0181 (6) |
C13 | 0.0901 (14) | 0.0534 (10) | 0.0558 (10) | −0.0222 (9) | 0.0024 (9) | −0.0084 (8) |
C14 | 0.0481 (8) | 0.0410 (7) | 0.0383 (7) | −0.0145 (6) | 0.0005 (6) | −0.0142 (6) |
C15 | 0.0498 (11) | 0.1063 (16) | 0.1244 (18) | −0.0131 (10) | 0.0252 (11) | −0.0724 (15) |
C16 | 0.0472 (8) | 0.0384 (7) | 0.0353 (7) | −0.0121 (6) | 0.0015 (5) | −0.0141 (6) |
C17 | 0.0461 (8) | 0.0406 (7) | 0.0468 (8) | −0.0126 (6) | 0.0019 (6) | −0.0174 (7) |
C18 | 0.0548 (9) | 0.0464 (8) | 0.0545 (9) | −0.0138 (7) | −0.0052 (7) | −0.0187 (7) |
C19 | 0.0580 (10) | 0.0601 (10) | 0.0800 (12) | −0.0174 (8) | −0.0080 (9) | −0.0345 (10) |
C20 | 0.0632 (11) | 0.0489 (10) | 0.0943 (14) | −0.0233 (8) | −0.0060 (10) | −0.0232 (10) |
C21 | 0.135 (2) | 0.0626 (12) | 0.0674 (12) | −0.0527 (13) | −0.0118 (12) | −0.0018 (10) |
C22 | 0.1237 (18) | 0.0644 (11) | 0.0501 (10) | −0.0479 (11) | −0.0086 (10) | −0.0094 (9) |
C23 | 0.0485 (9) | 0.0469 (8) | 0.0497 (8) | −0.0108 (7) | −0.0026 (7) | −0.0162 (7) |
C24 | 0.0481 (9) | 0.0561 (9) | 0.0554 (9) | −0.0155 (7) | 0.0021 (7) | −0.0275 (8) |
C25 | 0.0592 (10) | 0.0477 (9) | 0.0594 (9) | −0.0217 (7) | 0.0080 (7) | −0.0247 (8) |
C26 | 0.0566 (9) | 0.0450 (8) | 0.0446 (8) | −0.0169 (7) | 0.0121 (7) | −0.0173 (7) |
C27 | 0.0590 (9) | 0.0475 (8) | 0.0384 (7) | −0.0163 (7) | 0.0064 (6) | −0.0199 (6) |
C28 | 0.0930 (15) | 0.0577 (10) | 0.0511 (10) | −0.0259 (10) | 0.0081 (9) | −0.0110 (8) |
C29 | 0.0487 (8) | 0.0433 (8) | 0.0361 (7) | −0.0144 (6) | −0.0004 (6) | −0.0139 (6) |
C30 | 0.0547 (11) | 0.0817 (13) | 0.0786 (13) | 0.0045 (9) | 0.0004 (9) | −0.0342 (11) |
Geometric parameters (Å, º) top
O1—C9 | 1.226 (2) | C25—C26 | 1.332 (2) |
O2—C14 | 1.191 (2) | C26—C27 | 1.499 (2) |
O3—C14 | 1.3132 (18) | C26—C28 | 1.4861 (18) |
O3—C15 | 1.447 (2) | C3—H3 | 0.930 |
O4—C24 | 1.224 (2) | C4—H4 | 0.930 |
O5—C29 | 1.190 (2) | C5—H5 | 0.930 |
O6—C29 | 1.3207 (17) | C6—H6 | 0.930 |
O6—C30 | 1.443 (2) | C7—H7 | 0.930 |
C1—C2 | 1.536 (2) | C8—H81 | 0.970 |
C1—C8 | 1.528 (2) | C8—H82 | 0.970 |
C1—C12 | 1.5286 (17) | C10—H10 | 0.930 |
C1—C14 | 1.530 (2) | C12—H121 | 0.970 |
C2—C3 | 1.387 (2) | C12—H122 | 0.970 |
C2—C7 | 1.3830 (18) | C13—H131 | 0.960 |
C3—C4 | 1.388 (2) | C13—H132 | 0.960 |
C4—C5 | 1.365 (2) | C13—H133 | 0.960 |
C5—C6 | 1.367 (3) | C15—H151 | 0.960 |
C6—C7 | 1.376 (2) | C15—H152 | 0.960 |
C8—C9 | 1.503 (2) | C15—H153 | 0.960 |
C9—C10 | 1.4529 (19) | C18—H18 | 0.930 |
C10—C11 | 1.330 (2) | C19—H19 | 0.930 |
C11—C12 | 1.502 (2) | C20—H20 | 0.930 |
C11—C13 | 1.4910 (19) | C21—H21 | 0.930 |
C16—C17 | 1.532 (2) | C22—H22 | 0.930 |
C16—C23 | 1.532 (2) | C23—H231 | 0.970 |
C16—C27 | 1.5322 (17) | C23—H232 | 0.970 |
C16—C29 | 1.526 (2) | C25—H25 | 0.930 |
C17—C18 | 1.383 (2) | C27—H271 | 0.970 |
C17—C22 | 1.3726 (19) | C27—H272 | 0.970 |
C18—C19 | 1.380 (2) | C28—H281 | 0.960 |
C19—C20 | 1.358 (2) | C28—H282 | 0.960 |
C20—C21 | 1.354 (3) | C28—H283 | 0.960 |
C21—C22 | 1.377 (3) | C30—H301 | 0.960 |
C23—C24 | 1.507 (2) | C30—H302 | 0.960 |
C24—C25 | 1.4461 (19) | C30—H303 | 0.960 |
| | | |
O1···C6 | 3.539 (2) | H20···C3 | 3.428 |
O1···C15 | 3.457 (2) | H20···C13 | 3.228 |
O1···C25 | 3.484 (2) | H20···C15 | 3.096 |
O2···C27 | 3.204 (2) | H20···H3 | 3.231 |
O3···C20 | 3.444 (2) | H20···H82 | 3.420 |
O4···C12 | 3.547 (2) | H20···H121 | 3.283 |
O4···C21 | 3.419 (2) | H20···H131 | 3.436 |
O5···C12 | 3.309 (2) | H20···H132 | 2.655 |
C3···C19 | 3.573 (2) | H20···H133 | 3.116 |
C3···C20 | 3.451 (2) | H20···H152 | 2.590 |
C4···C19 | 3.438 (2) | H21···O4 | 2.824 |
C6···O1 | 3.539 (2) | H21···C30 | 3.326 |
C10···C30 | 3.441 (2) | H21···H4 | 3.219 |
C12···O4 | 3.547 (2) | H21···H82 | 3.506 |
C12···O5 | 3.309 (2) | H21···H132 | 2.842 |
C15···O1 | 3.457 (2) | H21···H301 | 3.458 |
C19···C3 | 3.573 (2) | H21···H303 | 2.458 |
C19···C4 | 3.438 (2) | H22···O4 | 3.261 |
C20···O3 | 3.444 (2) | H22···C3 | 3.497 |
C20···C3 | 3.451 (2) | H22···C4 | 3.399 |
C21···O4 | 3.419 (2) | H22···H3 | 3.031 |
C25···O1 | 3.484 (2) | H22···H4 | 2.850 |
C27···O2 | 3.204 (2) | H22···H231 | 3.459 |
C30···C10 | 3.441 (2) | H22···H232 | 3.598 |
O1···H6 | 2.628 | H25···O1 | 2.567 |
O1···H20 | 3.448 | H25···C9 | 3.378 |
O1···H25 | 2.567 | H25···C10 | 3.502 |
O1···H131 | 3.590 | H25···C15 | 3.511 |
O1···H152 | 2.541 | H25···C28 | 3.553 |
O1···H282 | 3.334 | H25···H10 | 2.940 |
O1···H283 | 2.939 | H25···H131 | 3.100 |
O2···H18 | 2.790 | H25···H152 | 2.977 |
O2···H271 | 2.616 | H25···H153 | 3.210 |
O2···H272 | 2.949 | H25···H282 | 3.393 |
O2···H281 | 3.436 | H25···H283 | 2.844 |
O2···H283 | 3.240 | H25···H302 | 3.568 |
O2···H302 | 3.319 | H81···C7 | 3.543 |
O3···H19 | 3.353 | H81···H6 | 3.111 |
O3···H20 | 2.679 | H81···H7 | 2.899 |
O3···H133 | 3.489 | H81···H272 | 3.405 |
O3···H301 | 3.324 | H82···C17 | 3.154 |
O4···H4 | 3.425 | H82···C18 | 3.042 |
O4···H10 | 2.863 | H82···C19 | 2.938 |
O4···H21 | 2.824 | H82···C20 | 2.936 |
O4···H22 | 3.261 | H82···C21 | 3.004 |
O4···H122 | 2.754 | H82···C22 | 3.108 |
O4···H131 | 2.964 | H82···H18 | 3.559 |
O4···H303 | 3.021 | H82···H19 | 3.414 |
O5···H3 | 2.746 | H82···H20 | 3.420 |
O5···H121 | 2.735 | H82···H21 | 3.506 |
O5···H122 | 3.018 | H121···O5 | 2.735 |
O5···H131 | 3.286 | H121···H20 | 3.283 |
O6···H4 | 3.361 | H121···H133 | 3.209 |
O6···H5 | 3.157 | H122···O4 | 2.754 |
O6···H153 | 3.170 | H122···O5 | 3.018 |
O6···H281 | 3.484 | H122···C23 | 3.528 |
C2···H232 | 3.173 | H122···C24 | 3.269 |
C3···H20 | 3.428 | H122···H231 | 2.880 |
C3···H22 | 3.497 | H131···O1 | 3.590 |
C3···H232 | 2.864 | H131···O4 | 2.964 |
C4···H22 | 3.399 | H131···O5 | 3.286 |
C4···H232 | 2.836 | H131···C10 | 3.537 |
C4···H303 | 3.514 | H131···C15 | 3.480 |
C5···H151 | 3.559 | H131···C24 | 3.177 |
C5···H232 | 3.095 | H131···C25 | 3.305 |
C5···H282 | 3.463 | H131···H10 | 2.981 |
C6···H19 | 3.406 | H131···H20 | 3.436 |
C6···H151 | 3.505 | H131···H25 | 3.100 |
C6···H232 | 3.363 | H131···H152 | 2.989 |
C6···H272 | 3.120 | H131···H153 | 3.306 |
C7···H19 | 3.494 | H132···C9 | 3.562 |
C7···H81 | 3.543 | H132···C10 | 3.204 |
C7···H232 | 3.398 | H132···C20 | 3.235 |
C7···H272 | 3.342 | H132···C21 | 3.335 |
C9···H6 | 3.518 | H132···H10 | 3.001 |
C9···H25 | 3.378 | H132···H20 | 2.655 |
C9···H132 | 3.562 | H132···H21 | 2.842 |
C9···H152 | 3.527 | H132···H152 | 3.450 |
C9···H283 | 3.452 | H132···H301 | 3.133 |
C10···H25 | 3.502 | H132···H303 | 3.289 |
C10···H131 | 3.537 | H133···O3 | 3.489 |
C10···H132 | 3.204 | H133···C30 | 3.577 |
C10···H301 | 3.137 | H133···H20 | 3.116 |
C10···H302 | 3.168 | H133···H121 | 3.209 |
C10···H303 | 3.458 | H133···H133 | 2.767 |
C11···H301 | 3.093 | H133···H152 | 3.534 |
C13···H10 | 3.335 | H133···H301 | 2.759 |
C13···H20 | 3.228 | H133···H303 | 3.591 |
C13···H152 | 3.506 | H151···C5 | 3.559 |
C13···H301 | 3.148 | H151···C6 | 3.505 |
C14···H18 | 3.583 | H151···C28 | 3.432 |
C14···H301 | 3.492 | H151···H5 | 3.154 |
C15···H6 | 3.511 | H151···H6 | 3.048 |
C15···H19 | 3.462 | H151···H18 | 3.287 |
C15···H20 | 3.096 | H151···H19 | 3.389 |
C15···H25 | 3.511 | H151···H271 | 3.459 |
C15···H131 | 3.480 | H151···H281 | 3.038 |
C15···H281 | 3.329 | H151···H282 | 3.033 |
C15···H282 | 3.257 | H152···O1 | 2.541 |
C15···H301 | 3.426 | H152···C9 | 3.527 |
C17···H82 | 3.154 | H152···C13 | 3.506 |
C18···H4 | 3.569 | H152···C19 | 3.549 |
C18···H7 | 3.531 | H152···C20 | 3.286 |
C18···H82 | 3.042 | H152···C25 | 3.471 |
C19···H4 | 3.594 | H152···H6 | 3.070 |
C19···H7 | 3.589 | H152···H19 | 3.110 |
C19···H82 | 2.938 | H152···H20 | 2.590 |
C19···H152 | 3.549 | H152···H25 | 2.977 |
C20···H3 | 3.350 | H152···H131 | 2.989 |
C20···H82 | 2.936 | H152···H132 | 3.450 |
C20···H132 | 3.235 | H152···H133 | 3.534 |
C20···H152 | 3.286 | H152···H282 | 3.118 |
C21···H82 | 3.004 | H153···O6 | 3.170 |
C21···H132 | 3.335 | H153···C25 | 3.281 |
C21···H303 | 3.358 | H153···C26 | 3.167 |
C22···H4 | 3.499 | H153···C28 | 3.184 |
C22···H82 | 3.108 | H153···C29 | 3.457 |
C23···H122 | 3.528 | H153···C30 | 3.182 |
C24···H122 | 3.269 | H153···H25 | 3.210 |
C24···H131 | 3.177 | H153···H131 | 3.306 |
C25···H10 | 3.593 | H153···H281 | 2.856 |
C25···H131 | 3.305 | H153···H282 | 3.070 |
C25···H152 | 3.471 | H153···H301 | 2.707 |
C25···H153 | 3.281 | H153···H302 | 3.229 |
C25···H283 | 3.450 | H231···H3 | 2.993 |
C26···H153 | 3.167 | H231···H22 | 3.459 |
C28···H5 | 3.305 | H231···H122 | 2.880 |
C28···H25 | 3.553 | H231···H231 | 3.291 |
C28···H151 | 3.432 | H232···C2 | 3.173 |
C28···H153 | 3.184 | H232···C3 | 2.864 |
C28···H282 | 3.314 | H232···C4 | 2.836 |
C28···H283 | 3.556 | H232···C5 | 3.095 |
C28···H302 | 2.975 | H232···C6 | 3.363 |
C29···H153 | 3.457 | H232···C7 | 3.398 |
C30···H4 | 3.473 | H232···H3 | 3.244 |
C30···H5 | 3.260 | H232···H4 | 3.212 |
C30···H10 | 3.164 | H232···H5 | 3.584 |
C30···H21 | 3.326 | H232···H22 | 3.598 |
C30···H133 | 3.577 | H271···O2 | 2.616 |
C30···H153 | 3.182 | H271···H151 | 3.459 |
C30···H281 | 3.387 | H272···O2 | 2.949 |
C30···H283 | 3.569 | H272···C6 | 3.120 |
H3···O5 | 2.746 | H272···C7 | 3.342 |
H3···C20 | 3.350 | H272···H6 | 3.114 |
H3···H20 | 3.231 | H272···H7 | 3.482 |
H3···H22 | 3.031 | H272···H81 | 3.405 |
H3···H231 | 2.993 | H281···O2 | 3.436 |
H3···H232 | 3.244 | H281···O6 | 3.484 |
H4···O4 | 3.425 | H281···C15 | 3.329 |
H4···O6 | 3.361 | H281···C30 | 3.387 |
H4···C18 | 3.569 | H281···H5 | 3.185 |
H4···C19 | 3.594 | H281···H151 | 3.038 |
H4···C22 | 3.499 | H281···H153 | 2.856 |
H4···C30 | 3.473 | H281···H302 | 2.578 |
H4···H21 | 3.219 | H282···O1 | 3.334 |
H4···H22 | 2.850 | H282···C5 | 3.463 |
H4···H232 | 3.212 | H282···C15 | 3.257 |
H4···H303 | 2.826 | H282···C28 | 3.314 |
H5···O6 | 3.157 | H282···H5 | 2.735 |
H5···C28 | 3.305 | H282···H6 | 3.191 |
H5···C30 | 3.260 | H282···H25 | 3.393 |
H5···H151 | 3.154 | H282···H151 | 3.033 |
H5···H232 | 3.584 | H282···H152 | 3.118 |
H5···H281 | 3.185 | H282···H153 | 3.070 |
H5···H282 | 2.735 | H282···H282 | 3.056 |
H5···H283 | 3.508 | H282···H283 | 2.923 |
H5···H302 | 3.021 | H282···H302 | 3.310 |
H5···H303 | 3.089 | H283···O1 | 2.939 |
H6···O1 | 2.628 | H283···O2 | 3.240 |
H6···C9 | 3.518 | H283···C9 | 3.452 |
H6···C15 | 3.511 | H283···C25 | 3.450 |
H6···H19 | 3.037 | H283···C28 | 3.556 |
H6···H81 | 3.111 | H283···C30 | 3.569 |
H6···H151 | 3.048 | H283···H5 | 3.508 |
H6···H152 | 3.070 | H283···H25 | 2.844 |
H6···H272 | 3.114 | H283···H282 | 2.923 |
H6···H282 | 3.191 | H283···H283 | 3.558 |
H7···C18 | 3.531 | H283···H302 | 2.615 |
H7···C19 | 3.589 | H301···O3 | 3.324 |
H7···H7 | 3.332 | H301···C10 | 3.137 |
H7···H18 | 3.076 | H301···C11 | 3.093 |
H7···H19 | 3.189 | H301···C13 | 3.148 |
H7···H81 | 2.899 | H301···C14 | 3.492 |
H7···H272 | 3.482 | H301···C15 | 3.426 |
H10···O4 | 2.863 | H301···H10 | 3.054 |
H10···C13 | 3.335 | H301···H21 | 3.458 |
H10···C25 | 3.593 | H301···H132 | 3.133 |
H10···C30 | 3.164 | H301···H133 | 2.759 |
H10···H25 | 2.940 | H301···H153 | 2.707 |
H10···H131 | 2.981 | H302···O2 | 3.319 |
H10···H132 | 3.001 | H302···C10 | 3.168 |
H10···H301 | 3.054 | H302···C28 | 2.975 |
H10···H302 | 2.955 | H302···H5 | 3.021 |
H10···H303 | 2.946 | H302···H10 | 2.955 |
H18···O2 | 2.790 | H302···H25 | 3.568 |
H18···C14 | 3.583 | H302···H153 | 3.229 |
H18···H7 | 3.076 | H302···H281 | 2.578 |
H18···H82 | 3.559 | H302···H282 | 3.310 |
H18···H151 | 3.287 | H302···H283 | 2.615 |
H19···O3 | 3.353 | H303···O4 | 3.021 |
H19···C6 | 3.406 | H303···C4 | 3.514 |
H19···C7 | 3.494 | H303···C10 | 3.458 |
H19···C15 | 3.462 | H303···C21 | 3.358 |
H19···H6 | 3.037 | H303···H4 | 2.826 |
H19···H7 | 3.189 | H303···H5 | 3.089 |
H19···H82 | 3.414 | H303···H10 | 2.946 |
H19···H151 | 3.389 | H303···H21 | 2.458 |
H19···H152 | 3.110 | H303···H132 | 3.289 |
H20···O1 | 3.448 | H303···H133 | 3.591 |
H20···O3 | 2.679 | | |
| | | |
C14—O3—C15 | 116.39 (15) | C7—C6—H6 | 119.9 |
C29—O6—C30 | 116.65 (13) | C2—C7—H7 | 119.4 |
C2—C1—C8 | 111.37 (10) | C6—C7—H7 | 119.4 |
C2—C1—C12 | 112.88 (14) | C1—C8—H81 | 108.5 |
C2—C1—C14 | 106.39 (11) | C1—C8—H82 | 108.5 |
C8—C1—C12 | 107.95 (12) | C9—C8—H81 | 108.5 |
C8—C1—C14 | 108.05 (13) | C9—C8—H82 | 108.5 |
C12—C1—C14 | 110.11 (9) | H81—C8—H82 | 109.5 |
C1—C2—C3 | 122.22 (11) | C9—C10—H10 | 118.8 |
C1—C2—C7 | 119.85 (15) | C11—C10—H10 | 118.8 |
C3—C2—C7 | 117.91 (15) | C1—C12—H121 | 108.6 |
C2—C3—C4 | 120.56 (13) | C1—C12—H122 | 108.6 |
C3—C4—C5 | 120.2 (2) | C11—C12—H121 | 108.6 |
C4—C5—C6 | 119.92 (18) | C11—C12—H122 | 108.6 |
C5—C6—C7 | 120.19 (15) | H121—C12—H122 | 109.5 |
C2—C7—C6 | 121.20 (18) | C11—C13—H131 | 109.5 |
C1—C8—C9 | 113.14 (11) | C11—C13—H132 | 109.5 |
O1—C9—C8 | 121.05 (13) | C11—C13—H133 | 109.5 |
O1—C9—C10 | 121.73 (16) | H131—C13—H132 | 109.5 |
C8—C9—C10 | 117.17 (17) | H131—C13—H133 | 109.5 |
C9—C10—C11 | 122.42 (16) | H132—C13—H133 | 109.5 |
C10—C11—C12 | 121.60 (12) | O3—C15—H151 | 109.5 |
C10—C11—C13 | 122.57 (16) | O3—C15—H152 | 109.5 |
C12—C11—C13 | 115.83 (16) | O3—C15—H153 | 109.5 |
C1—C12—C11 | 113.06 (14) | H151—C15—H152 | 109.5 |
O2—C14—O3 | 122.74 (14) | H151—C15—H153 | 109.5 |
O2—C14—C1 | 124.28 (13) | H152—C15—H153 | 109.5 |
O3—C14—C1 | 112.98 (13) | C17—C18—H18 | 119.6 |
C17—C16—C23 | 111.39 (10) | C19—C18—H18 | 119.6 |
C17—C16—C27 | 112.53 (13) | C18—C19—H19 | 119.7 |
C17—C16—C29 | 106.44 (12) | C20—C19—H19 | 119.7 |
C23—C16—C27 | 108.04 (12) | C19—C20—H20 | 120.3 |
C23—C16—C29 | 108.26 (13) | C21—C20—H20 | 120.3 |
C27—C16—C29 | 110.11 (10) | C20—C21—H21 | 119.7 |
C16—C17—C18 | 122.24 (11) | C22—C21—H21 | 119.7 |
C16—C17—C22 | 120.48 (17) | C17—C22—H22 | 119.3 |
C18—C17—C22 | 117.28 (17) | C21—C22—H22 | 119.3 |
C17—C18—C19 | 120.86 (14) | C16—C23—H231 | 108.4 |
C18—C19—C20 | 120.5 (2) | C16—C23—H232 | 108.4 |
C19—C20—C21 | 119.4 (2) | C24—C23—H231 | 108.4 |
C20—C21—C22 | 120.51 (17) | C24—C23—H232 | 108.4 |
C17—C22—C21 | 121.4 (2) | H231—C23—H232 | 109.5 |
C16—C23—C24 | 113.60 (11) | C24—C25—H25 | 118.7 |
O4—C24—C23 | 120.40 (13) | C26—C25—H25 | 118.7 |
O4—C24—C25 | 121.99 (18) | C16—C27—H271 | 108.6 |
C23—C24—C25 | 117.57 (16) | C16—C27—H272 | 108.6 |
C24—C25—C26 | 122.52 (17) | C26—C27—H271 | 108.6 |
C25—C26—C27 | 121.46 (12) | C26—C27—H272 | 108.6 |
C25—C26—C28 | 122.66 (16) | H271—C27—H272 | 109.5 |
C27—C26—C28 | 115.88 (15) | C26—C28—H281 | 109.5 |
C16—C27—C26 | 112.89 (14) | C26—C28—H282 | 109.5 |
O5—C29—O6 | 122.31 (13) | C26—C28—H283 | 109.5 |
O5—C29—C16 | 124.80 (12) | H281—C28—H282 | 109.5 |
O6—C29—C16 | 112.87 (13) | H281—C28—H283 | 109.5 |
C2—C3—H3 | 119.7 | H282—C28—H283 | 109.5 |
C4—C3—H3 | 119.7 | O6—C30—H301 | 109.5 |
C3—C4—H4 | 119.9 | O6—C30—H302 | 109.5 |
C5—C4—H4 | 119.9 | O6—C30—H303 | 109.5 |
C4—C5—H5 | 120.0 | H301—C30—H302 | 109.5 |
C6—C5—H5 | 120.0 | H301—C30—H303 | 109.5 |
C5—C6—H6 | 119.9 | H302—C30—H303 | 109.5 |
| | | |
C15—O3—C14—O2 | −4.0 (2) | C10—C11—C12—C1 | 24.1 (2) |
C15—O3—C14—C1 | 175.59 (14) | C13—C11—C12—C1 | −156.62 (13) |
C30—O6—C29—O5 | 1.5 (2) | C17—C16—C23—C24 | −176.24 (12) |
C30—O6—C29—C16 | −177.29 (14) | C23—C16—C17—C18 | 138.26 (14) |
C2—C1—C8—C9 | 178.77 (13) | C23—C16—C17—C22 | −42.22 (19) |
C8—C1—C2—C3 | −131.95 (14) | C17—C16—C27—C26 | 174.86 (11) |
C8—C1—C2—C7 | 49.37 (18) | C27—C16—C17—C18 | 16.75 (18) |
C2—C1—C12—C11 | −174.33 (11) | C27—C16—C17—C22 | −163.73 (15) |
C12—C1—C2—C3 | −10.33 (18) | C17—C16—C29—O5 | −100.91 (19) |
C12—C1—C2—C7 | 170.99 (13) | C17—C16—C29—O6 | 77.80 (14) |
C2—C1—C14—O2 | 104.06 (17) | C29—C16—C17—C18 | −103.94 (15) |
C2—C1—C14—O3 | −75.56 (13) | C29—C16—C17—C22 | 75.58 (17) |
C14—C1—C2—C3 | 110.54 (14) | C23—C16—C27—C26 | 51.47 (16) |
C14—C1—C2—C7 | −68.14 (16) | C27—C16—C23—C24 | −52.15 (17) |
C8—C1—C12—C11 | −50.80 (16) | C23—C16—C29—O5 | 18.9 (2) |
C12—C1—C8—C9 | 54.32 (18) | C23—C16—C29—O6 | −162.36 (12) |
C8—C1—C14—O2 | −15.62 (18) | C29—C16—C23—C24 | 67.07 (15) |
C8—C1—C14—O3 | 164.76 (11) | C27—C16—C29—O5 | 136.85 (17) |
C14—C1—C8—C9 | −64.73 (15) | C27—C16—C29—O6 | −44.44 (19) |
C12—C1—C14—O2 | −133.30 (16) | C29—C16—C27—C26 | −66.58 (17) |
C12—C1—C14—O3 | 47.08 (18) | C16—C17—C18—C19 | 178.51 (13) |
C14—C1—C12—C11 | 66.94 (17) | C16—C17—C22—C21 | −178.77 (18) |
C1—C2—C3—C4 | −178.40 (13) | C18—C17—C22—C21 | 0.8 (2) |
C1—C2—C7—C6 | 179.17 (14) | C22—C17—C18—C19 | −1.0 (2) |
C3—C2—C7—C6 | 0.4 (2) | C17—C18—C19—C20 | 0.2 (2) |
C7—C2—C3—C4 | 0.3 (2) | C18—C19—C20—C21 | 0.9 (2) |
C2—C3—C4—C5 | −0.8 (2) | C19—C20—C21—C22 | −1.1 (3) |
C3—C4—C5—C6 | 0.7 (2) | C20—C21—C22—C17 | 0.3 (3) |
C4—C5—C6—C7 | 0.1 (2) | C16—C23—C24—O4 | −156.11 (15) |
C5—C6—C7—C2 | −0.6 (2) | C16—C23—C24—C25 | 26.2 (2) |
C1—C8—C9—O1 | 151.74 (15) | O4—C24—C25—C26 | −174.21 (16) |
C1—C8—C9—C10 | −30.6 (2) | C23—C24—C25—C26 | 3.5 (2) |
O1—C9—C10—C11 | 178.37 (16) | C24—C25—C26—C27 | −3.9 (2) |
C8—C9—C10—C11 | 0.8 (2) | C24—C25—C26—C28 | 175.33 (15) |
C9—C10—C11—C12 | 2.6 (2) | C25—C26—C27—C16 | −25.3 (2) |
C9—C10—C11—C13 | −176.68 (15) | C28—C26—C27—C16 | 155.46 (13) |