The molecular conformation is stabilized by an intramolecular O—H

O hydrogen bond between the hydroxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit.
Supporting information
CCDC reference: 2061379
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact H12A ..H14A . 1.97 Ang.
x,y,z = 1_555 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B ..O2 . 2.66 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 3 Report
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 2 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for O3A --C15 . 12.5 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for C16 --C17A . 11.5 s.u.
PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 6% Note
PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C14 - C15 . 1.51 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 81 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 19 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
8 ALERT level G = General information/check it is not something unexpected
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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Ethyl
2-[9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodecahydroacridin-10-yl]acetate
top
Crystal data top
C27H33NO5 | F(000) = 968 |
Mr = 451.54 | Dx = 1.229 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.5289 (2) Å | Cell parameters from 3784 reflections |
b = 18.6653 (5) Å | θ = 4.0–71.4° |
c = 13.8046 (3) Å | µ = 0.68 mm−1 |
β = 96.410 (2)° | T = 173 K |
V = 2439.93 (10) Å3 | Plate, yellow |
Z = 4 | 0.48 × 0.22 × 0.08 mm |
Data collection top
Rigaku Oxford Diffraction EOS diffractometer | 4648 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 3949 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.2°, θmin = 4.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysalisPro; Rigaku OD, 2015) | k = −22→14 |
Tmin = 0.861, Tmax = 1.000 | l = −16→16 |
9527 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.6477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4648 reflections | Δρmax = 0.27 e Å−3 |
313 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | |
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 | Occ. (<1) |
O1 | 0.65518 (12) | 0.22713 (7) | 0.50403 (8) | 0.0373 (3) | |
O2 | 0.21715 (14) | 0.36821 (7) | 0.51857 (8) | 0.0426 (3) | |
O3 | 0.3445 (5) | 0.11473 (19) | 0.83632 (16) | 0.0636 (11) | 0.777 (9) |
O3A | 0.2813 (17) | 0.1388 (6) | 0.8394 (7) | 0.0636 (11) | 0.223 (9) |
O4 | 0.35606 (14) | 0.14006 (6) | 0.99586 (9) | 0.0406 (3) | |
O5 | 0.41985 (13) | 0.19489 (7) | 0.39430 (8) | 0.0389 (3) | |
H5 | 0.4887 | 0.2122 | 0.4300 | 0.058* | |
N1 | 0.44568 (13) | 0.24991 (6) | 0.79603 (8) | 0.0236 (2) | |
C1 | 0.54686 (14) | 0.22154 (7) | 0.74277 (10) | 0.0228 (3) | |
C2 | 0.66871 (16) | 0.18305 (8) | 0.79873 (11) | 0.0292 (3) | |
H2A | 0.6309 | 0.1464 | 0.8407 | 0.035* | |
H2B | 0.7234 | 0.2179 | 0.8419 | 0.035* | |
C3 | 0.76892 (16) | 0.14645 (9) | 0.73461 (12) | 0.0328 (3) | |
C4 | 0.79512 (16) | 0.19849 (9) | 0.65285 (12) | 0.0356 (4) | |
H4A | 0.8424 | 0.2421 | 0.6814 | 0.043* | |
H4B | 0.8587 | 0.1758 | 0.6098 | 0.043* | |
C5 | 0.65908 (16) | 0.21917 (8) | 0.59366 (11) | 0.0286 (3) | |
C6 | 0.53718 (15) | 0.23162 (8) | 0.64433 (10) | 0.0245 (3) | |
C7 | 0.40195 (15) | 0.25806 (8) | 0.58758 (10) | 0.0244 (3) | |
H7 | 0.4283 | 0.2880 | 0.5323 | 0.029* | |
C8 | 0.32755 (14) | 0.30588 (7) | 0.65354 (10) | 0.0237 (3) | |
C9 | 0.22950 (16) | 0.35939 (8) | 0.60657 (11) | 0.0291 (3) | |
C10 | 0.14223 (16) | 0.40152 (9) | 0.67124 (12) | 0.0323 (3) | |
H10A | 0.0581 | 0.3731 | 0.6833 | 0.039* | |
H10B | 0.1091 | 0.4463 | 0.6376 | 0.039* | |
C11 | 0.22671 (16) | 0.42010 (8) | 0.76873 (11) | 0.0280 (3) | |
C12 | 0.27846 (15) | 0.34965 (8) | 0.81805 (10) | 0.0263 (3) | |
H12A | 0.3461 | 0.3608 | 0.8758 | 0.032* | |
H12B | 0.1970 | 0.3245 | 0.8411 | 0.032* | |
C13 | 0.34886 (14) | 0.30040 (7) | 0.75185 (10) | 0.0222 (3) | |
C14 | 0.43949 (15) | 0.22835 (8) | 0.89738 (10) | 0.0256 (3) | |
H14A | 0.3858 | 0.2646 | 0.9304 | 0.031* | |
H14B | 0.5365 | 0.2265 | 0.9315 | 0.031* | |
C15 | 0.37019 (19) | 0.15605 (9) | 0.90423 (12) | 0.0368 (4) | |
C16 | 0.2856 (3) | 0.07304 (12) | 1.01388 (17) | 0.0641 (7) | |
H16A | 0.3553 | 0.0335 | 1.0218 | 0.077* | 0.725 (5) |
H16B | 0.2146 | 0.0615 | 0.9581 | 0.077* | 0.725 (5) |
H16C | 0.2872 | 0.0420 | 0.9559 | 0.077* | 0.275 (5) |
H16D | 0.3405 | 0.0485 | 1.0693 | 0.077* | 0.275 (5) |
C17 | 0.2157 (4) | 0.08124 (19) | 1.1040 (3) | 0.0665 (9) | 0.725 (5) |
H17A | 0.2875 | 0.0880 | 1.1598 | 0.100* | 0.725 (5) |
H17B | 0.1604 | 0.0381 | 1.1141 | 0.100* | 0.725 (5) |
H17C | 0.1530 | 0.1230 | 1.0976 | 0.100* | 0.725 (5) |
C17A | 0.1551 (11) | 0.0790 (5) | 1.0331 (8) | 0.0665 (9) | 0.275 (5) |
H17D | 0.1499 | 0.1142 | 1.0853 | 0.100* | 0.275 (5) |
H17E | 0.1217 | 0.0324 | 1.0541 | 0.100* | 0.275 (5) |
H17F | 0.0956 | 0.0947 | 0.9745 | 0.100* | 0.275 (5) |
C18 | 0.30828 (15) | 0.19663 (8) | 0.54418 (10) | 0.0258 (3) | |
C19 | 0.32270 (16) | 0.16932 (9) | 0.45105 (11) | 0.0307 (3) | |
C20 | 0.23375 (19) | 0.11504 (10) | 0.41156 (13) | 0.0405 (4) | |
H20 | 0.2428 | 0.0976 | 0.3479 | 0.049* | |
C21 | 0.13242 (18) | 0.08647 (9) | 0.46441 (14) | 0.0410 (4) | |
H21 | 0.0723 | 0.0493 | 0.4371 | 0.049* | |
C22 | 0.11833 (17) | 0.11164 (9) | 0.55659 (13) | 0.0356 (4) | |
H22 | 0.0494 | 0.0916 | 0.5933 | 0.043* | |
C23 | 0.20564 (16) | 0.16652 (8) | 0.59556 (11) | 0.0295 (3) | |
H23 | 0.1949 | 0.1839 | 0.6590 | 0.035* | |
C24 | 0.7045 (2) | 0.07682 (10) | 0.69143 (15) | 0.0469 (4) | |
H24A | 0.6894 | 0.0436 | 0.7443 | 0.070* | |
H24B | 0.7688 | 0.0550 | 0.6493 | 0.070* | |
H24C | 0.6139 | 0.0872 | 0.6531 | 0.070* | |
C25 | 0.9082 (2) | 0.12973 (11) | 0.79789 (14) | 0.0468 (4) | |
H25A | 0.9533 | 0.1746 | 0.8214 | 0.070* | |
H25B | 0.9713 | 0.1036 | 0.7590 | 0.070* | |
H25C | 0.8887 | 0.1003 | 0.8537 | 0.070* | |
C26 | 0.13320 (19) | 0.45952 (9) | 0.83469 (13) | 0.0405 (4) | |
H26A | 0.0495 | 0.4305 | 0.8424 | 0.061* | |
H26B | 0.1038 | 0.5057 | 0.8052 | 0.061* | |
H26C | 0.1864 | 0.4677 | 0.8987 | 0.061* | |
C27 | 0.35163 (17) | 0.46822 (8) | 0.75087 (12) | 0.0340 (3) | |
H27A | 0.4061 | 0.4799 | 0.8133 | 0.051* | |
H27B | 0.3163 | 0.5125 | 0.7187 | 0.051* | |
H27C | 0.4123 | 0.4431 | 0.7092 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0375 (6) | 0.0503 (7) | 0.0266 (6) | −0.0016 (5) | 0.0144 (4) | −0.0032 (5) |
O2 | 0.0548 (7) | 0.0469 (7) | 0.0249 (6) | 0.0155 (6) | −0.0006 (5) | 0.0006 (5) |
O3 | 0.114 (3) | 0.0437 (16) | 0.0360 (8) | −0.0364 (17) | 0.0192 (12) | −0.0122 (10) |
O3A | 0.114 (3) | 0.0437 (16) | 0.0360 (8) | −0.0364 (17) | 0.0192 (12) | −0.0122 (10) |
O4 | 0.0571 (7) | 0.0352 (6) | 0.0317 (6) | −0.0098 (5) | 0.0158 (5) | 0.0055 (5) |
O5 | 0.0448 (6) | 0.0485 (7) | 0.0245 (5) | 0.0025 (5) | 0.0080 (5) | −0.0075 (5) |
N1 | 0.0288 (6) | 0.0242 (6) | 0.0189 (5) | 0.0020 (5) | 0.0069 (4) | −0.0005 (4) |
C1 | 0.0248 (6) | 0.0203 (6) | 0.0241 (7) | −0.0020 (5) | 0.0064 (5) | −0.0023 (5) |
C2 | 0.0305 (7) | 0.0316 (7) | 0.0257 (7) | 0.0041 (6) | 0.0035 (6) | −0.0014 (6) |
C3 | 0.0324 (8) | 0.0323 (8) | 0.0344 (8) | 0.0071 (6) | 0.0065 (6) | −0.0027 (6) |
C4 | 0.0290 (8) | 0.0417 (9) | 0.0382 (9) | 0.0041 (6) | 0.0125 (6) | −0.0014 (7) |
C5 | 0.0309 (7) | 0.0280 (7) | 0.0287 (7) | −0.0025 (6) | 0.0109 (6) | −0.0038 (6) |
C6 | 0.0269 (7) | 0.0244 (7) | 0.0233 (7) | −0.0005 (5) | 0.0073 (5) | −0.0025 (5) |
C7 | 0.0303 (7) | 0.0246 (7) | 0.0190 (6) | 0.0010 (6) | 0.0065 (5) | −0.0012 (5) |
C8 | 0.0260 (6) | 0.0226 (7) | 0.0233 (7) | −0.0010 (5) | 0.0059 (5) | −0.0021 (5) |
C9 | 0.0312 (7) | 0.0294 (7) | 0.0261 (7) | 0.0006 (6) | 0.0010 (6) | −0.0025 (6) |
C10 | 0.0304 (7) | 0.0318 (8) | 0.0345 (8) | 0.0063 (6) | 0.0028 (6) | −0.0016 (6) |
C11 | 0.0327 (7) | 0.0243 (7) | 0.0277 (7) | 0.0043 (6) | 0.0072 (6) | −0.0017 (6) |
C12 | 0.0323 (7) | 0.0241 (7) | 0.0236 (7) | 0.0020 (6) | 0.0088 (5) | −0.0016 (5) |
C13 | 0.0245 (6) | 0.0195 (6) | 0.0232 (7) | −0.0018 (5) | 0.0064 (5) | −0.0010 (5) |
C14 | 0.0325 (7) | 0.0267 (7) | 0.0187 (6) | 0.0019 (6) | 0.0068 (5) | 0.0003 (5) |
C15 | 0.0492 (9) | 0.0353 (8) | 0.0269 (8) | −0.0090 (7) | 0.0085 (6) | 0.0001 (6) |
C16 | 0.0987 (18) | 0.0460 (12) | 0.0520 (12) | −0.0294 (12) | 0.0280 (12) | 0.0052 (9) |
C17 | 0.082 (2) | 0.0543 (16) | 0.070 (2) | −0.0088 (15) | 0.0384 (17) | 0.0188 (17) |
C17A | 0.082 (2) | 0.0543 (16) | 0.070 (2) | −0.0088 (15) | 0.0384 (17) | 0.0188 (17) |
C18 | 0.0286 (7) | 0.0242 (7) | 0.0239 (7) | 0.0051 (5) | −0.0003 (5) | −0.0014 (5) |
C19 | 0.0338 (8) | 0.0323 (8) | 0.0256 (7) | 0.0080 (6) | 0.0015 (6) | −0.0029 (6) |
C20 | 0.0479 (9) | 0.0391 (9) | 0.0326 (8) | 0.0063 (7) | −0.0039 (7) | −0.0137 (7) |
C21 | 0.0388 (9) | 0.0307 (8) | 0.0503 (10) | 0.0005 (7) | −0.0097 (7) | −0.0093 (7) |
C22 | 0.0344 (8) | 0.0281 (8) | 0.0434 (9) | 0.0008 (6) | −0.0001 (7) | 0.0019 (7) |
C23 | 0.0328 (7) | 0.0274 (7) | 0.0280 (7) | 0.0026 (6) | 0.0021 (6) | −0.0002 (6) |
C24 | 0.0588 (11) | 0.0312 (9) | 0.0514 (11) | 0.0062 (8) | 0.0094 (8) | −0.0059 (8) |
C25 | 0.0405 (10) | 0.0533 (11) | 0.0463 (10) | 0.0185 (8) | 0.0037 (8) | −0.0019 (8) |
C26 | 0.0469 (10) | 0.0344 (8) | 0.0418 (9) | 0.0118 (7) | 0.0124 (7) | −0.0053 (7) |
C27 | 0.0409 (8) | 0.0247 (7) | 0.0363 (8) | −0.0019 (6) | 0.0034 (6) | 0.0005 (6) |
Geometric parameters (Å, º) top
O1—C5 | 1.2426 (19) | C12—C13 | 1.5057 (18) |
O2—C9 | 1.2185 (19) | C14—H14A | 0.9900 |
O3—C15 | 1.217 (3) | C14—H14B | 0.9900 |
O3A—C15 | 1.205 (11) | C14—C15 | 1.510 (2) |
O4—C15 | 1.321 (2) | C16—H16A | 0.9900 |
O4—C16 | 1.454 (2) | C16—H16B | 0.9900 |
O5—H5 | 0.8400 | C16—H16C | 0.9900 |
O5—C19 | 1.364 (2) | C16—H16D | 0.9900 |
N1—C1 | 1.3816 (18) | C16—C17 | 1.483 (4) |
N1—C13 | 1.4091 (18) | C16—C17A | 1.305 (9) |
N1—C14 | 1.4633 (17) | C17—H17A | 0.9800 |
C1—C2 | 1.504 (2) | C17—H17B | 0.9800 |
C1—C6 | 1.365 (2) | C17—H17C | 0.9800 |
C2—H2A | 0.9900 | C17A—H17D | 0.9800 |
C2—H2B | 0.9900 | C17A—H17E | 0.9800 |
C2—C3 | 1.533 (2) | C17A—H17F | 0.9800 |
C3—C4 | 1.531 (2) | C18—C19 | 1.404 (2) |
C3—C24 | 1.530 (2) | C18—C23 | 1.389 (2) |
C3—C25 | 1.537 (2) | C19—C20 | 1.392 (2) |
C4—H4A | 0.9900 | C20—H20 | 0.9500 |
C4—H4B | 0.9900 | C20—C21 | 1.381 (3) |
C4—C5 | 1.504 (2) | C21—H21 | 0.9500 |
C5—C6 | 1.4401 (19) | C21—C22 | 1.377 (3) |
C6—C7 | 1.514 (2) | C22—H22 | 0.9500 |
C7—H7 | 1.0000 | C22—C23 | 1.390 (2) |
C7—C8 | 1.5074 (18) | C23—H23 | 0.9500 |
C7—C18 | 1.5334 (19) | C24—H24A | 0.9800 |
C8—C9 | 1.468 (2) | C24—H24B | 0.9800 |
C8—C13 | 1.354 (2) | C24—H24C | 0.9800 |
C9—C10 | 1.507 (2) | C25—H25A | 0.9800 |
C10—H10A | 0.9900 | C25—H25B | 0.9800 |
C10—H10B | 0.9900 | C25—H25C | 0.9800 |
C10—C11 | 1.529 (2) | C26—H26A | 0.9800 |
C11—C12 | 1.537 (2) | C26—H26B | 0.9800 |
C11—C26 | 1.532 (2) | C26—H26C | 0.9800 |
C11—C27 | 1.533 (2) | C27—H27A | 0.9800 |
C12—H12A | 0.9900 | C27—H27B | 0.9800 |
C12—H12B | 0.9900 | C27—H27C | 0.9800 |
| | | |
C15—O4—C16 | 117.16 (15) | O3—C15—O4 | 124.13 (18) |
C19—O5—H5 | 109.5 | O3—C15—C14 | 124.71 (17) |
C1—N1—C13 | 119.22 (11) | O3A—C15—O4 | 120.8 (5) |
C1—N1—C14 | 120.56 (12) | O3A—C15—C14 | 117.9 (5) |
C13—N1—C14 | 120.23 (11) | O4—C15—C14 | 110.73 (13) |
N1—C1—C2 | 117.03 (12) | O4—C16—H16A | 110.0 |
C6—C1—N1 | 120.23 (13) | O4—C16—H16B | 110.0 |
C6—C1—C2 | 122.68 (13) | O4—C16—H16C | 108.4 |
C1—C2—H2A | 108.7 | O4—C16—H16D | 108.4 |
C1—C2—H2B | 108.7 | O4—C16—C17 | 108.3 (2) |
C1—C2—C3 | 114.28 (12) | H16A—C16—H16B | 108.4 |
H2A—C2—H2B | 107.6 | H16C—C16—H16D | 107.5 |
C3—C2—H2A | 108.7 | C17—C16—H16A | 110.0 |
C3—C2—H2B | 108.7 | C17—C16—H16B | 110.0 |
C2—C3—C25 | 108.42 (13) | C17A—C16—O4 | 115.5 (4) |
C4—C3—C2 | 107.84 (13) | C17A—C16—H16C | 108.4 |
C4—C3—C25 | 110.27 (14) | C17A—C16—H16D | 108.4 |
C24—C3—C2 | 110.77 (14) | C16—C17—H17A | 109.5 |
C24—C3—C4 | 110.08 (14) | C16—C17—H17B | 109.5 |
C24—C3—C25 | 109.43 (15) | C16—C17—H17C | 109.5 |
C3—C4—H4A | 109.4 | H17A—C17—H17B | 109.5 |
C3—C4—H4B | 109.4 | H17A—C17—H17C | 109.5 |
H4A—C4—H4B | 108.0 | H17B—C17—H17C | 109.5 |
C5—C4—C3 | 111.22 (13) | C16—C17A—H17D | 109.5 |
C5—C4—H4A | 109.4 | C16—C17A—H17E | 109.5 |
C5—C4—H4B | 109.4 | C16—C17A—H17F | 109.5 |
O1—C5—C4 | 119.99 (13) | H17D—C17A—H17E | 109.5 |
O1—C5—C6 | 121.89 (14) | H17D—C17A—H17F | 109.5 |
C6—C5—C4 | 118.08 (13) | H17E—C17A—H17F | 109.5 |
C1—C6—C5 | 119.53 (13) | C19—C18—C7 | 121.14 (13) |
C1—C6—C7 | 121.28 (12) | C23—C18—C7 | 121.01 (13) |
C5—C6—C7 | 119.16 (12) | C23—C18—C19 | 117.85 (14) |
C6—C7—H7 | 107.8 | O5—C19—C18 | 122.76 (14) |
C6—C7—C18 | 112.53 (11) | O5—C19—C20 | 116.89 (14) |
C8—C7—C6 | 108.12 (11) | C20—C19—C18 | 120.34 (15) |
C8—C7—H7 | 107.8 | C19—C20—H20 | 119.8 |
C8—C7—C18 | 112.73 (11) | C21—C20—C19 | 120.35 (15) |
C18—C7—H7 | 107.8 | C21—C20—H20 | 119.8 |
C9—C8—C7 | 117.07 (12) | C20—C21—H21 | 119.9 |
C13—C8—C7 | 122.19 (13) | C22—C21—C20 | 120.17 (15) |
C13—C8—C9 | 120.73 (13) | C22—C21—H21 | 119.9 |
O2—C9—C8 | 121.20 (14) | C21—C22—H22 | 120.2 |
O2—C9—C10 | 121.44 (14) | C21—C22—C23 | 119.56 (16) |
C8—C9—C10 | 117.34 (13) | C23—C22—H22 | 120.2 |
C9—C10—H10A | 109.3 | C18—C23—C22 | 121.71 (14) |
C9—C10—H10B | 109.3 | C18—C23—H23 | 119.1 |
C9—C10—C11 | 111.62 (12) | C22—C23—H23 | 119.1 |
H10A—C10—H10B | 108.0 | C3—C24—H24A | 109.5 |
C11—C10—H10A | 109.3 | C3—C24—H24B | 109.5 |
C11—C10—H10B | 109.3 | C3—C24—H24C | 109.5 |
C10—C11—C12 | 107.90 (12) | H24A—C24—H24B | 109.5 |
C10—C11—C26 | 110.38 (13) | H24A—C24—H24C | 109.5 |
C10—C11—C27 | 109.47 (13) | H24B—C24—H24C | 109.5 |
C26—C11—C12 | 109.08 (12) | C3—C25—H25A | 109.5 |
C26—C11—C27 | 109.14 (13) | C3—C25—H25B | 109.5 |
C27—C11—C12 | 110.87 (12) | C3—C25—H25C | 109.5 |
C11—C12—H12A | 108.9 | H25A—C25—H25B | 109.5 |
C11—C12—H12B | 108.9 | H25A—C25—H25C | 109.5 |
H12A—C12—H12B | 107.7 | H25B—C25—H25C | 109.5 |
C13—C12—C11 | 113.34 (12) | C11—C26—H26A | 109.5 |
C13—C12—H12A | 108.9 | C11—C26—H26B | 109.5 |
C13—C12—H12B | 108.9 | C11—C26—H26C | 109.5 |
N1—C13—C12 | 117.39 (12) | H26A—C26—H26B | 109.5 |
C8—C13—N1 | 120.15 (12) | H26A—C26—H26C | 109.5 |
C8—C13—C12 | 122.36 (13) | H26B—C26—H26C | 109.5 |
N1—C14—H14A | 109.3 | C11—C27—H27A | 109.5 |
N1—C14—H14B | 109.3 | C11—C27—H27B | 109.5 |
N1—C14—C15 | 111.74 (12) | C11—C27—H27C | 109.5 |
H14A—C14—H14B | 107.9 | H27A—C27—H27B | 109.5 |
C15—C14—H14A | 109.3 | H27A—C27—H27C | 109.5 |
C15—C14—H14B | 109.3 | H27B—C27—H27C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1 | 0.84 | 1.81 | 2.6319 (17) | 166 |
C2—H2A···O2i | 0.99 | 2.52 | 3.1663 (19) | 123 |
C2—H2B···O5i | 0.99 | 2.53 | 3.457 (2) | 157 |
C12—H12B···O1ii | 0.99 | 2.52 | 3.2708 (17) | 133 |
C14—H14A···O1ii | 0.99 | 2.53 | 3.3299 (18) | 138 |
C14—H14B···O2i | 0.99 | 2.66 | 3.473 (2) | 140 |
C27—H27B···O3iii | 0.98 | 2.51 | 3.452 (3) | 161 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2. |
Short H···H interatomic contacts (Å) in the title compound topContact | Distance | Symmetry operation |
H21···H27A | 2.26 | -1/2 + x, 1/2 - y, -1/2 + z |
H22···H27A | 2.46 | 1/2 - x, -1/2 + y, 3/2 - z |
H22···H4B | 2.43 | -1 + x, y, z |