In the title compound, molecules are linked together by O—H
O and C—H
O hydrogen bonds, forming zigzag chains that are parallel to the (001) plane and run along the
b-axis direction. van der Waals interactions between these chains along the
a and
c axes maintain the molecular packing.
Supporting information
CCDC reference: 2254247
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X H5O ..H27A . 1.86 Ang.
x,y,z = 1_555 Check
Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X H5O ..H26C . 1.91 Ang.
x,y,z = 1_555 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 3 Report
Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing .............. 0.00010 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing .............. 0.00017 Ang.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 51 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 20 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).
2,2'-[(3,5-Di-
tert-butyl-4-hydroxyphenyl)methanediyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)
top
Crystal data top
C31H44O5 | F(000) = 1080 |
Mr = 496.66 | Dx = 1.189 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 12.40591 (9) Å | Cell parameters from 41183 reflections |
b = 10.98934 (10) Å | θ = 3.6–77.8° |
c = 20.58063 (17) Å | µ = 0.63 mm−1 |
β = 98.4293 (7)° | T = 100 K |
V = 2775.50 (4) Å3 | Prism, colourless |
Z = 4 | 0.33 × 0.21 × 0.18 mm |
Data collection top
XtaLAB Synergy, Dualflex, HyPix diffractometer | 5540 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.047 |
φ and ω scans | θmax = 77.9°, θmin = 3.6° |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022) | h = −13→15 |
Tmin = 0.362, Tmax = 1.000 | k = −13→13 |
61789 measured reflections | l = −26→26 |
5870 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.9674P] where P = (Fo2 + 2Fc2)/3 |
5870 reflections | (Δ/σ)max = 0.001 |
347 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.67352 (6) | 0.68092 (7) | 0.79581 (4) | 0.02223 (17) | |
H1O | 0.7151 (15) | 0.6706 (16) | 0.7621 (9) | 0.046 (5)* | |
O2 | 0.39003 (6) | 0.48506 (8) | 0.65828 (4) | 0.02641 (18) | |
O3 | 0.47791 (6) | 0.57142 (7) | 0.55974 (4) | 0.02175 (17) | |
H3O | 0.4532 (15) | 0.5356 (17) | 0.5969 (9) | 0.049 (5)* | |
O4 | 0.79022 (6) | 0.69306 (7) | 0.69970 (3) | 0.01951 (16) | |
O5 | 0.99582 (6) | 0.26695 (8) | 0.81386 (4) | 0.02279 (17) | |
H5O | 1.0464 (15) | 0.2572 (16) | 0.7907 (9) | 0.041 (4)* | |
C1 | 0.61903 (8) | 0.51072 (9) | 0.68241 (5) | 0.0160 (2) | |
H1 | 0.5758 | 0.4455 | 0.6566 | 0.019* | |
C2 | 0.54278 (8) | 0.56043 (9) | 0.72776 (5) | 0.0171 (2) | |
C3 | 0.57463 (8) | 0.63356 (9) | 0.78073 (5) | 0.0186 (2) | |
C4 | 0.50033 (9) | 0.66692 (11) | 0.82932 (6) | 0.0245 (2) | |
H4A | 0.4701 | 0.7491 | 0.8186 | 0.029* | |
H4B | 0.5435 | 0.6707 | 0.8737 | 0.029* | |
C5 | 0.40583 (9) | 0.57748 (10) | 0.83053 (5) | 0.0217 (2) | |
C6 | 0.35058 (9) | 0.56319 (12) | 0.75965 (6) | 0.0265 (2) | |
H6A | 0.2947 | 0.4985 | 0.7579 | 0.032* | |
H6B | 0.3127 | 0.6401 | 0.7454 | 0.032* | |
C7 | 0.42799 (9) | 0.53188 (10) | 0.71194 (5) | 0.0211 (2) | |
C8 | 0.32572 (10) | 0.62886 (12) | 0.87359 (6) | 0.0307 (3) | |
H8A | 0.3632 | 0.6401 | 0.9185 | 0.046* | |
H8B | 0.2650 | 0.5719 | 0.8739 | 0.046* | |
H8C | 0.2977 | 0.7073 | 0.8559 | 0.046* | |
C9 | 0.44652 (10) | 0.45389 (12) | 0.85835 (6) | 0.0304 (3) | |
H9A | 0.4965 | 0.4189 | 0.8307 | 0.046* | |
H9B | 0.3844 | 0.3991 | 0.8590 | 0.046* | |
H9C | 0.4848 | 0.4646 | 0.9031 | 0.046* | |
C10 | 0.64598 (8) | 0.60075 (9) | 0.63062 (5) | 0.0162 (2) | |
C11 | 0.57732 (8) | 0.61877 (9) | 0.57293 (5) | 0.0176 (2) | |
C12 | 0.60567 (8) | 0.69745 (10) | 0.51805 (5) | 0.0197 (2) | |
H12A | 0.5757 | 0.7800 | 0.5224 | 0.024* | |
H12B | 0.5709 | 0.6634 | 0.4756 | 0.024* | |
C13 | 0.72887 (8) | 0.70697 (10) | 0.51767 (5) | 0.0192 (2) | |
C14 | 0.78192 (8) | 0.74319 (10) | 0.58701 (5) | 0.0193 (2) | |
H14A | 0.8614 | 0.7292 | 0.5905 | 0.023* | |
H14B | 0.7707 | 0.8315 | 0.5926 | 0.023* | |
C15 | 0.74074 (8) | 0.67709 (9) | 0.64281 (5) | 0.0169 (2) | |
C16 | 0.75463 (10) | 0.80530 (11) | 0.46958 (6) | 0.0266 (2) | |
H16A | 0.7221 | 0.8826 | 0.4804 | 0.040* | |
H16B | 0.7244 | 0.7814 | 0.4247 | 0.040* | |
H16C | 0.8338 | 0.8148 | 0.4728 | 0.040* | |
C17 | 0.77368 (9) | 0.58492 (10) | 0.49695 (5) | 0.0231 (2) | |
H17A | 0.8532 | 0.5899 | 0.5002 | 0.035* | |
H17B | 0.7422 | 0.5667 | 0.4515 | 0.035* | |
H17C | 0.7543 | 0.5202 | 0.5259 | 0.035* | |
C18 | 0.72031 (8) | 0.44419 (9) | 0.71819 (5) | 0.0169 (2) | |
C19 | 0.80443 (8) | 0.41235 (9) | 0.68346 (5) | 0.0176 (2) | |
H19 | 0.7982 | 0.4341 | 0.6384 | 0.021* | |
C20 | 0.89755 (8) | 0.34983 (9) | 0.71204 (5) | 0.0174 (2) | |
C21 | 0.90520 (8) | 0.32072 (9) | 0.77939 (5) | 0.0177 (2) | |
C22 | 0.82019 (8) | 0.34622 (9) | 0.81580 (5) | 0.0175 (2) | |
C23 | 0.72883 (8) | 0.40755 (9) | 0.78330 (5) | 0.0177 (2) | |
H23 | 0.6702 | 0.4248 | 0.8068 | 0.021* | |
C24 | 0.98864 (9) | 0.31798 (10) | 0.67141 (5) | 0.0206 (2) | |
C25 | 0.95624 (10) | 0.35071 (13) | 0.59845 (5) | 0.0307 (3) | |
H25A | 0.8885 | 0.3087 | 0.5811 | 0.046* | |
H25B | 1.0142 | 0.3255 | 0.5738 | 0.046* | |
H25C | 0.9454 | 0.4388 | 0.5941 | 0.046* | |
C26 | 1.09148 (9) | 0.39337 (11) | 0.69613 (6) | 0.0249 (2) | |
H26A | 1.0742 | 0.4803 | 0.6916 | 0.037* | |
H26B | 1.1491 | 0.3734 | 0.6700 | 0.037* | |
H26C | 1.1164 | 0.3743 | 0.7424 | 0.037* | |
C27 | 1.01253 (9) | 0.17986 (11) | 0.67306 (6) | 0.0249 (2) | |
H27A | 1.0304 | 0.1529 | 0.7188 | 0.037* | |
H27B | 1.0742 | 0.1632 | 0.6496 | 0.037* | |
H27C | 0.9481 | 0.1359 | 0.6519 | 0.037* | |
C28 | 0.82892 (9) | 0.31386 (10) | 0.88945 (5) | 0.0190 (2) | |
C29 | 0.72191 (9) | 0.33977 (11) | 0.91629 (5) | 0.0248 (2) | |
H29A | 0.7048 | 0.4267 | 0.9118 | 0.037* | |
H29B | 0.7299 | 0.3167 | 0.9628 | 0.037* | |
H29C | 0.6628 | 0.2924 | 0.8914 | 0.037* | |
C30 | 0.85384 (9) | 0.17769 (10) | 0.90225 (5) | 0.0221 (2) | |
H30A | 0.7966 | 0.1284 | 0.8769 | 0.033* | |
H30B | 0.8564 | 0.1604 | 0.9492 | 0.033* | |
H30C | 0.9244 | 0.1578 | 0.8888 | 0.033* | |
C31 | 0.91838 (9) | 0.39252 (10) | 0.92908 (5) | 0.0235 (2) | |
H31A | 0.9879 | 0.3783 | 0.9130 | 0.035* | |
H31B | 0.9254 | 0.3705 | 0.9757 | 0.035* | |
H31C | 0.8987 | 0.4787 | 0.9237 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0206 (4) | 0.0269 (4) | 0.0198 (4) | −0.0059 (3) | 0.0049 (3) | −0.0048 (3) |
O2 | 0.0183 (4) | 0.0367 (5) | 0.0231 (4) | −0.0052 (3) | −0.0008 (3) | −0.0003 (3) |
O3 | 0.0160 (4) | 0.0296 (4) | 0.0183 (4) | −0.0029 (3) | −0.0017 (3) | −0.0008 (3) |
O4 | 0.0183 (4) | 0.0242 (4) | 0.0154 (3) | −0.0040 (3) | 0.0005 (3) | −0.0014 (3) |
O5 | 0.0179 (4) | 0.0335 (4) | 0.0168 (3) | 0.0085 (3) | 0.0021 (3) | 0.0044 (3) |
C1 | 0.0152 (5) | 0.0165 (5) | 0.0156 (4) | −0.0006 (4) | 0.0002 (3) | −0.0001 (4) |
C2 | 0.0156 (5) | 0.0178 (5) | 0.0178 (5) | 0.0016 (4) | 0.0017 (4) | 0.0031 (4) |
C3 | 0.0178 (5) | 0.0184 (5) | 0.0196 (5) | 0.0007 (4) | 0.0030 (4) | 0.0029 (4) |
C4 | 0.0252 (6) | 0.0245 (5) | 0.0254 (5) | −0.0009 (4) | 0.0093 (4) | −0.0035 (4) |
C5 | 0.0180 (5) | 0.0250 (5) | 0.0231 (5) | 0.0034 (4) | 0.0061 (4) | 0.0048 (4) |
C6 | 0.0157 (5) | 0.0384 (7) | 0.0255 (6) | 0.0018 (4) | 0.0034 (4) | 0.0043 (5) |
C7 | 0.0175 (5) | 0.0236 (5) | 0.0215 (5) | 0.0004 (4) | 0.0008 (4) | 0.0044 (4) |
C8 | 0.0269 (6) | 0.0366 (7) | 0.0312 (6) | 0.0074 (5) | 0.0129 (5) | 0.0055 (5) |
C9 | 0.0268 (6) | 0.0315 (6) | 0.0352 (6) | 0.0062 (5) | 0.0124 (5) | 0.0131 (5) |
C10 | 0.0162 (5) | 0.0165 (5) | 0.0157 (4) | 0.0008 (4) | 0.0015 (4) | −0.0007 (3) |
C11 | 0.0169 (5) | 0.0182 (5) | 0.0173 (5) | 0.0016 (4) | 0.0009 (4) | −0.0022 (4) |
C12 | 0.0198 (5) | 0.0221 (5) | 0.0161 (5) | 0.0021 (4) | −0.0007 (4) | 0.0009 (4) |
C13 | 0.0203 (5) | 0.0225 (5) | 0.0145 (5) | 0.0002 (4) | 0.0015 (4) | 0.0016 (4) |
C14 | 0.0191 (5) | 0.0210 (5) | 0.0177 (5) | −0.0030 (4) | 0.0022 (4) | 0.0002 (4) |
C15 | 0.0165 (5) | 0.0180 (5) | 0.0159 (4) | 0.0018 (4) | 0.0016 (4) | −0.0009 (4) |
C16 | 0.0274 (6) | 0.0315 (6) | 0.0210 (5) | −0.0006 (5) | 0.0033 (4) | 0.0075 (4) |
C17 | 0.0234 (5) | 0.0273 (6) | 0.0185 (5) | 0.0028 (4) | 0.0033 (4) | −0.0015 (4) |
C18 | 0.0160 (5) | 0.0163 (5) | 0.0177 (5) | 0.0002 (4) | 0.0005 (4) | 0.0001 (4) |
C19 | 0.0189 (5) | 0.0190 (5) | 0.0147 (4) | 0.0002 (4) | 0.0015 (4) | 0.0004 (4) |
C20 | 0.0165 (5) | 0.0188 (5) | 0.0166 (5) | 0.0005 (4) | 0.0017 (4) | −0.0007 (4) |
C21 | 0.0167 (5) | 0.0184 (5) | 0.0170 (5) | 0.0018 (4) | −0.0003 (4) | 0.0011 (4) |
C22 | 0.0193 (5) | 0.0175 (5) | 0.0155 (5) | 0.0004 (4) | 0.0017 (4) | 0.0007 (4) |
C23 | 0.0168 (5) | 0.0183 (5) | 0.0182 (5) | 0.0012 (4) | 0.0036 (4) | 0.0004 (4) |
C24 | 0.0178 (5) | 0.0278 (6) | 0.0164 (5) | 0.0046 (4) | 0.0032 (4) | 0.0019 (4) |
C25 | 0.0249 (6) | 0.0499 (8) | 0.0182 (5) | 0.0127 (5) | 0.0067 (4) | 0.0051 (5) |
C26 | 0.0192 (5) | 0.0281 (6) | 0.0279 (5) | 0.0018 (4) | 0.0048 (4) | 0.0071 (4) |
C27 | 0.0223 (5) | 0.0286 (6) | 0.0235 (5) | 0.0050 (4) | 0.0024 (4) | −0.0053 (4) |
C28 | 0.0211 (5) | 0.0209 (5) | 0.0151 (5) | 0.0025 (4) | 0.0029 (4) | 0.0012 (4) |
C29 | 0.0258 (6) | 0.0315 (6) | 0.0184 (5) | 0.0060 (4) | 0.0072 (4) | 0.0039 (4) |
C30 | 0.0265 (5) | 0.0211 (5) | 0.0186 (5) | 0.0018 (4) | 0.0028 (4) | 0.0031 (4) |
C31 | 0.0272 (6) | 0.0237 (5) | 0.0189 (5) | 0.0006 (4) | 0.0011 (4) | −0.0018 (4) |
Geometric parameters (Å, º) top
O1—C3 | 1.3268 (13) | C14—H14B | 0.9900 |
O1—H1O | 0.930 (19) | C16—H16A | 0.9800 |
O2—C7 | 1.2466 (14) | C16—H16B | 0.9800 |
O3—C11 | 1.3293 (13) | C16—H16C | 0.9800 |
O3—H3O | 0.950 (19) | C17—H17A | 0.9800 |
O4—C15 | 1.2521 (12) | C17—H17B | 0.9800 |
O5—C21 | 1.3720 (12) | C17—H17C | 0.9800 |
O5—H5O | 0.848 (19) | C18—C23 | 1.3882 (14) |
C1—C2 | 1.5241 (14) | C18—C19 | 1.3931 (14) |
C1—C10 | 1.5270 (14) | C19—C20 | 1.3977 (14) |
C1—C18 | 1.5442 (13) | C19—H19 | 0.9500 |
C1—H1 | 1.0000 | C20—C21 | 1.4121 (14) |
C2—C3 | 1.3654 (15) | C20—C24 | 1.5414 (14) |
C2—C7 | 1.4479 (14) | C21—C22 | 1.4085 (14) |
C3—C4 | 1.5015 (14) | C22—C23 | 1.4014 (14) |
C4—C5 | 1.5329 (15) | C22—C28 | 1.5453 (13) |
C4—H4A | 0.9900 | C23—H23 | 0.9500 |
C4—H4B | 0.9900 | C24—C25 | 1.5390 (14) |
C5—C6 | 1.5262 (16) | C24—C26 | 1.5436 (16) |
C5—C9 | 1.5305 (15) | C24—C27 | 1.5459 (16) |
C5—C8 | 1.5329 (15) | C25—H25A | 0.9800 |
C6—C7 | 1.5104 (15) | C25—H25B | 0.9800 |
C6—H6A | 0.9900 | C25—H25C | 0.9800 |
C6—H6B | 0.9900 | C26—H26A | 0.9800 |
C8—H8A | 0.9800 | C26—H26B | 0.9800 |
C8—H8B | 0.9800 | C26—H26C | 0.9800 |
C8—H8C | 0.9800 | C27—H27A | 0.9800 |
C9—H9A | 0.9800 | C27—H27B | 0.9800 |
C9—H9B | 0.9800 | C27—H27C | 0.9800 |
C9—H9C | 0.9800 | C28—C29 | 1.5373 (14) |
C10—C11 | 1.3703 (14) | C28—C31 | 1.5423 (15) |
C10—C15 | 1.4361 (14) | C28—C30 | 1.5429 (14) |
C11—C12 | 1.5044 (14) | C29—H29A | 0.9800 |
C12—C13 | 1.5332 (14) | C29—H29B | 0.9800 |
C12—H12A | 0.9900 | C29—H29C | 0.9800 |
C12—H12B | 0.9900 | C30—H30A | 0.9800 |
C13—C16 | 1.5305 (15) | C30—H30B | 0.9800 |
C13—C14 | 1.5338 (14) | C30—H30C | 0.9800 |
C13—C17 | 1.5360 (15) | C31—H31A | 0.9800 |
C14—C15 | 1.5098 (14) | C31—H31B | 0.9800 |
C14—H14A | 0.9900 | C31—H31C | 0.9800 |
| | | |
C3—O1—H1O | 111.9 (11) | H16A—C16—H16B | 109.5 |
C11—O3—H3O | 113.4 (11) | C13—C16—H16C | 109.5 |
C21—O5—H5O | 112.4 (12) | H16A—C16—H16C | 109.5 |
C2—C1—C10 | 114.48 (8) | H16B—C16—H16C | 109.5 |
C2—C1—C18 | 114.35 (8) | C13—C17—H17A | 109.5 |
C10—C1—C18 | 113.17 (8) | C13—C17—H17B | 109.5 |
C2—C1—H1 | 104.4 | H17A—C17—H17B | 109.5 |
C10—C1—H1 | 104.4 | C13—C17—H17C | 109.5 |
C18—C1—H1 | 104.4 | H17A—C17—H17C | 109.5 |
C3—C2—C7 | 117.84 (9) | H17B—C17—H17C | 109.5 |
C3—C2—C1 | 124.54 (9) | C23—C18—C19 | 117.75 (9) |
C7—C2—C1 | 117.58 (9) | C23—C18—C1 | 122.62 (9) |
O1—C3—C2 | 124.54 (9) | C19—C18—C1 | 119.51 (9) |
O1—C3—C4 | 112.67 (9) | C18—C19—C20 | 122.87 (9) |
C2—C3—C4 | 122.78 (10) | C18—C19—H19 | 118.6 |
C3—C4—C5 | 113.58 (9) | C20—C19—H19 | 118.6 |
C3—C4—H4A | 108.9 | C19—C20—C21 | 117.18 (9) |
C5—C4—H4A | 108.9 | C19—C20—C24 | 120.65 (9) |
C3—C4—H4B | 108.9 | C21—C20—C24 | 122.14 (9) |
C5—C4—H4B | 108.9 | O5—C21—C22 | 115.54 (9) |
H4A—C4—H4B | 107.7 | O5—C21—C20 | 122.49 (9) |
C6—C5—C9 | 110.09 (10) | C22—C21—C20 | 121.96 (9) |
C6—C5—C4 | 106.73 (9) | C23—C22—C21 | 117.25 (9) |
C9—C5—C4 | 111.35 (9) | C23—C22—C28 | 120.95 (9) |
C6—C5—C8 | 110.61 (9) | C21—C22—C28 | 121.73 (9) |
C9—C5—C8 | 108.47 (9) | C18—C23—C22 | 122.82 (9) |
C4—C5—C8 | 109.60 (10) | C18—C23—H23 | 118.6 |
C7—C6—C5 | 113.92 (9) | C22—C23—H23 | 118.6 |
C7—C6—H6A | 108.8 | C25—C24—C20 | 111.64 (9) |
C5—C6—H6A | 108.8 | C25—C24—C26 | 106.33 (9) |
C7—C6—H6B | 108.8 | C20—C24—C26 | 109.60 (9) |
C5—C6—H6B | 108.8 | C25—C24—C27 | 105.83 (9) |
H6A—C6—H6B | 107.7 | C20—C24—C27 | 111.38 (9) |
O2—C7—C2 | 121.33 (10) | C26—C24—C27 | 111.91 (9) |
O2—C7—C6 | 118.45 (10) | C24—C25—H25A | 109.5 |
C2—C7—C6 | 120.18 (10) | C24—C25—H25B | 109.5 |
C5—C8—H8A | 109.5 | H25A—C25—H25B | 109.5 |
C5—C8—H8B | 109.5 | C24—C25—H25C | 109.5 |
H8A—C8—H8B | 109.5 | H25A—C25—H25C | 109.5 |
C5—C8—H8C | 109.5 | H25B—C25—H25C | 109.5 |
H8A—C8—H8C | 109.5 | C24—C26—H26A | 109.5 |
H8B—C8—H8C | 109.5 | C24—C26—H26B | 109.5 |
C5—C9—H9A | 109.5 | H26A—C26—H26B | 109.5 |
C5—C9—H9B | 109.5 | C24—C26—H26C | 109.5 |
H9A—C9—H9B | 109.5 | H26A—C26—H26C | 109.5 |
C5—C9—H9C | 109.5 | H26B—C26—H26C | 109.5 |
H9A—C9—H9C | 109.5 | C24—C27—H27A | 109.5 |
H9B—C9—H9C | 109.5 | C24—C27—H27B | 109.5 |
C11—C10—C15 | 117.13 (9) | H27A—C27—H27B | 109.5 |
C11—C10—C1 | 121.77 (9) | C24—C27—H27C | 109.5 |
C15—C10—C1 | 120.93 (8) | H27A—C27—H27C | 109.5 |
O3—C11—C10 | 124.11 (9) | H27B—C27—H27C | 109.5 |
O3—C11—C12 | 112.55 (8) | C29—C28—C31 | 107.37 (9) |
C10—C11—C12 | 123.32 (9) | C29—C28—C30 | 106.28 (9) |
C11—C12—C13 | 112.71 (8) | C31—C28—C30 | 110.04 (9) |
C11—C12—H12A | 109.1 | C29—C28—C22 | 111.71 (8) |
C13—C12—H12A | 109.0 | C31—C28—C22 | 109.34 (8) |
C11—C12—H12B | 109.0 | C30—C28—C22 | 111.97 (8) |
C13—C12—H12B | 109.1 | C28—C29—H29A | 109.5 |
H12A—C12—H12B | 107.8 | C28—C29—H29B | 109.5 |
C16—C13—C12 | 110.75 (9) | H29A—C29—H29B | 109.5 |
C16—C13—C14 | 108.46 (9) | C28—C29—H29C | 109.5 |
C12—C13—C14 | 107.76 (8) | H29A—C29—H29C | 109.5 |
C16—C13—C17 | 108.58 (9) | H29B—C29—H29C | 109.5 |
C12—C13—C17 | 110.09 (9) | C28—C30—H30A | 109.5 |
C14—C13—C17 | 111.20 (8) | C28—C30—H30B | 109.5 |
C15—C14—C13 | 115.84 (9) | H30A—C30—H30B | 109.5 |
C15—C14—H14A | 108.3 | C28—C30—H30C | 109.5 |
C13—C14—H14A | 108.3 | H30A—C30—H30C | 109.5 |
C15—C14—H14B | 108.3 | H30B—C30—H30C | 109.5 |
C13—C14—H14B | 108.3 | C28—C31—H31A | 109.5 |
H14A—C14—H14B | 107.4 | C28—C31—H31B | 109.5 |
O4—C15—C10 | 121.45 (9) | H31A—C31—H31B | 109.5 |
O4—C15—C14 | 118.02 (9) | C28—C31—H31C | 109.5 |
C10—C15—C14 | 120.51 (9) | H31A—C31—H31C | 109.5 |
C13—C16—H16A | 109.5 | H31B—C31—H31C | 109.5 |
C13—C16—H16B | 109.5 | | |
| | | |
C10—C1—C2—C3 | −80.31 (12) | C11—C10—C15—O4 | 159.09 (10) |
C18—C1—C2—C3 | 52.59 (13) | C1—C10—C15—O4 | −16.20 (15) |
C10—C1—C2—C7 | 97.16 (11) | C11—C10—C15—C14 | −19.37 (14) |
C18—C1—C2—C7 | −129.95 (9) | C1—C10—C15—C14 | 165.34 (9) |
C7—C2—C3—O1 | −170.29 (10) | C13—C14—C15—O4 | 171.74 (9) |
C1—C2—C3—O1 | 7.17 (16) | C13—C14—C15—C10 | −9.75 (14) |
C7—C2—C3—C4 | 10.96 (15) | C2—C1—C18—C23 | 14.42 (14) |
C1—C2—C3—C4 | −171.58 (9) | C10—C1—C18—C23 | 147.93 (10) |
O1—C3—C4—C5 | −156.69 (9) | C2—C1—C18—C19 | −169.61 (9) |
C2—C3—C4—C5 | 22.20 (15) | C10—C1—C18—C19 | −36.10 (13) |
C3—C4—C5—C6 | −51.77 (12) | C23—C18—C19—C20 | −2.46 (15) |
C3—C4—C5—C9 | 68.40 (12) | C1—C18—C19—C20 | −178.62 (9) |
C3—C4—C5—C8 | −171.58 (9) | C18—C19—C20—C21 | −1.08 (15) |
C9—C5—C6—C7 | −69.22 (12) | C18—C19—C20—C24 | −179.42 (10) |
C4—C5—C6—C7 | 51.76 (13) | C19—C20—C21—O5 | −175.48 (9) |
C8—C5—C6—C7 | 170.91 (10) | C24—C20—C21—O5 | 2.84 (16) |
C3—C2—C7—O2 | 166.72 (10) | C19—C20—C21—C22 | 3.91 (15) |
C1—C2—C7—O2 | −10.92 (15) | C24—C20—C21—C22 | −177.77 (10) |
C3—C2—C7—C6 | −10.86 (15) | O5—C21—C22—C23 | 176.38 (9) |
C1—C2—C7—C6 | 171.50 (9) | C20—C21—C22—C23 | −3.06 (15) |
C5—C6—C7—O2 | 159.86 (10) | O5—C21—C22—C28 | −0.72 (14) |
C5—C6—C7—C2 | −22.50 (15) | C20—C21—C22—C28 | 179.85 (9) |
C2—C1—C10—C11 | −82.41 (12) | C19—C18—C23—C22 | 3.40 (15) |
C18—C1—C10—C11 | 144.14 (9) | C1—C18—C23—C22 | 179.43 (9) |
C2—C1—C10—C15 | 92.66 (11) | C21—C22—C23—C18 | −0.72 (15) |
C18—C1—C10—C15 | −40.79 (12) | C28—C22—C23—C18 | 176.40 (10) |
C15—C10—C11—O3 | −167.64 (9) | C19—C20—C24—C25 | −6.12 (15) |
C1—C10—C11—O3 | 7.61 (15) | C21—C20—C24—C25 | 175.62 (10) |
C15—C10—C11—C12 | 10.77 (15) | C19—C20—C24—C26 | 111.43 (11) |
C1—C10—C11—C12 | −173.97 (9) | C21—C20—C24—C26 | −66.83 (13) |
O3—C11—C12—C13 | −155.18 (9) | C19—C20—C24—C27 | −124.18 (10) |
C10—C11—C12—C13 | 26.24 (14) | C21—C20—C24—C27 | 57.56 (13) |
C11—C12—C13—C16 | −169.61 (9) | C23—C22—C28—C29 | 8.36 (14) |
C11—C12—C13—C14 | −51.12 (11) | C21—C22—C28—C29 | −174.66 (10) |
C11—C12—C13—C17 | 70.30 (11) | C23—C22—C28—C31 | −110.35 (11) |
C16—C13—C14—C15 | 163.76 (9) | C21—C22—C28—C31 | 66.63 (12) |
C12—C13—C14—C15 | 43.82 (12) | C23—C22—C28—C30 | 127.43 (10) |
C17—C13—C14—C15 | −76.92 (11) | C21—C22—C28—C30 | −55.59 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4 | 0.930 (19) | 1.711 (19) | 2.6201 (11) | 164.7 (17) |
O3—H3O···O2 | 0.950 (19) | 1.68 (2) | 2.6174 (11) | 170.3 (17) |
O5—H5O···O4i | 0.848 (19) | 2.128 (18) | 2.8285 (11) | 139.7 (16) |
C14—H14A···O5ii | 0.99 | 2.48 | 3.1912 (12) | 128 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2. |
Summary of short interatomic contacts (Å) in the title compound topH4B···H16B | 2.39 | x, 3/2 - y, 1/2 + z |
H4A···H1 | 2.31 | 1 - x, 1/2 + y, 3/2 - z |
H17B···O2 | 2.65 | 1 - x, 1 - y, 1 - z |
O4···H5O | 2.12 | 2 - x, 1/2 + y, 3/2 - z |
C17···H30B | 3.10 | x, 1/2 - y, -1/2 + z |
H26C···H6A | 2.58 | 1 + x, y, z |
H25B···H17A | 2.57 | 2 - x, 1 - y, 1 - z |