In the title compound, C
30H
24N
2O·0.5C
4H
8O
2, the piperidone ring adopts the chair conformation and all the phenyl rings are equatorially oriented. The ethyl acetate molecule is present as a space filler and does not participate in the hydrogen-bonding network. The crystal structure is stabilized through C—H
N and C—H
O hydrogen bonds. No significant C—H
π and π–π interactions are observed.
Supporting information
CCDC reference: 604948
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.067
- wR factor = 0.188
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C8
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 73
C6 -N1 -C7 -N2 91.00 3.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 74
C2 -N1 -C7 -N2 -130.00 3.00 1.555 1.555 1.555 1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
6 ALERT type 4 Improvement, methodology, query or suggestion
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.
J. Suresh, R.V. Krishnakumar, S. Natarajan have
contributed to the crystallization, structure solution
and analysis, respectively.
V.P. Alex Raja and S. Perumal have contributed to the
synthesis of the compound under study.
A. Mostad have contributed to the X-ray intensity data
collection using SMART APEX CCD diffractometer.
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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
4-Oxo-2,3,5,6-tetraphenylpiperidine-1-carbonitrile ethyl acetate hemisolvate
top
Crystal data top
C30H24N2O·0.5C4H8O2 | F(000) = 1000 |
Mr = 472.56 | Dx = 1.178 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6611 reflections |
a = 9.3887 (3) Å | θ = 2–23° |
b = 10.6241 (4) Å | µ = 0.07 mm−1 |
c = 26.7247 (10) Å | T = 105 K |
β = 92.232 (2)° | Block, colourless |
V = 2663.67 (17) Å3 | 0.26 × 0.18 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 6596 independent reflections |
Radiation source: fine-focus sealed tube | 5640 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −12→12 |
Tmin = 0.97, Tmax = 0.99 | k = −14→14 |
40759 measured reflections | l = −35→35 |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0737P)2 + 2.1461P] where P = (Fo2 + 2Fc2)/3 |
6596 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.46 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) 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) |
O1 | 0.04789 (14) | 0.00962 (15) | 0.16462 (5) | 0.0379 (3) | |
N1 | 0.37233 (15) | 0.21068 (14) | 0.22197 (5) | 0.0236 (3) | |
N2 | 0.5316 (2) | 0.38502 (19) | 0.25107 (7) | 0.0422 (4) | |
C2 | 0.35442 (17) | 0.19334 (16) | 0.16675 (6) | 0.0231 (3) | |
H2 | 0.2843 | 0.2544 | 0.1536 | 0.028* | |
C3 | 0.29627 (17) | 0.05854 (16) | 0.15663 (6) | 0.0229 (3) | |
H3 | 0.3671 | −0.0011 | 0.1704 | 0.027* | |
C4 | 0.15975 (18) | 0.04043 (16) | 0.18499 (6) | 0.0249 (3) | |
C5 | 0.17797 (17) | 0.06278 (15) | 0.24111 (6) | 0.0228 (3) | |
H5 | 0.2477 | 0.0013 | 0.2542 | 0.027* | |
C6 | 0.24167 (17) | 0.19602 (16) | 0.25125 (6) | 0.0227 (3) | |
H6 | 0.1717 | 0.2596 | 0.2401 | 0.027* | |
C21 | 0.49415 (18) | 0.21525 (17) | 0.14176 (6) | 0.0258 (3) | |
C22 | 0.5014 (2) | 0.30455 (19) | 0.10375 (7) | 0.0360 (4) | |
H22 | 0.4209 | 0.3510 | 0.0942 | 0.043* | |
C23 | 0.6291 (3) | 0.3243 (2) | 0.08012 (9) | 0.0462 (5) | |
H23 | 0.6333 | 0.3833 | 0.0545 | 0.055* | |
C24 | 0.7490 (2) | 0.2568 (2) | 0.09442 (9) | 0.0454 (5) | |
H24 | 0.8343 | 0.2715 | 0.0789 | 0.054* | |
C25 | 0.7431 (2) | 0.1670 (2) | 0.13200 (8) | 0.0403 (5) | |
H25 | 0.8239 | 0.1207 | 0.1413 | 0.048* | |
C26 | 0.61552 (19) | 0.1463 (2) | 0.15572 (7) | 0.0327 (4) | |
H26 | 0.6114 | 0.0862 | 0.1809 | 0.039* | |
C31 | 0.27867 (19) | 0.03343 (17) | 0.10105 (6) | 0.0266 (3) | |
C32 | 0.1788 (2) | 0.0978 (2) | 0.07103 (7) | 0.0359 (4) | |
H32 | 0.1190 | 0.1563 | 0.0853 | 0.043* | |
C33 | 0.1679 (3) | 0.0751 (2) | 0.01975 (8) | 0.0451 (5) | |
H33 | 0.1010 | 0.1187 | −0.0002 | 0.054* | |
C34 | 0.2556 (3) | −0.0116 (3) | −0.00149 (8) | 0.0547 (7) | |
H34 | 0.2481 | −0.0268 | −0.0358 | 0.066* | |
C35 | 0.3539 (4) | −0.0756 (3) | 0.02779 (9) | 0.0629 (8) | |
H35 | 0.4133 | −0.1341 | 0.0133 | 0.075* | |
C36 | 0.3658 (3) | −0.0538 (2) | 0.07909 (8) | 0.0450 (5) | |
H36 | 0.4327 | −0.0982 | 0.0987 | 0.054* | |
C51 | 0.04357 (18) | 0.04548 (16) | 0.26973 (6) | 0.0255 (3) | |
C52 | 0.0447 (2) | −0.03692 (17) | 0.31024 (7) | 0.0298 (4) | |
H52 | 0.1260 | −0.0838 | 0.3182 | 0.036* | |
C53 | −0.0751 (2) | −0.0495 (2) | 0.33877 (8) | 0.0375 (4) | |
H53 | −0.0730 | −0.1040 | 0.3660 | 0.045* | |
C54 | −0.1973 (2) | 0.0186 (2) | 0.32698 (8) | 0.0403 (5) | |
H54 | −0.2777 | 0.0089 | 0.3459 | 0.048* | |
C55 | −0.1994 (2) | 0.1016 (2) | 0.28677 (8) | 0.0391 (5) | |
H55 | −0.2811 | 0.1481 | 0.2788 | 0.047* | |
C56 | −0.07939 (19) | 0.11489 (19) | 0.25840 (7) | 0.0323 (4) | |
H56 | −0.0812 | 0.1707 | 0.2316 | 0.039* | |
C61 | 0.27605 (18) | 0.21387 (16) | 0.30663 (6) | 0.0244 (3) | |
C62 | 0.1967 (2) | 0.29970 (19) | 0.33330 (7) | 0.0336 (4) | |
H62 | 0.1278 | 0.3488 | 0.3167 | 0.040* | |
C63 | 0.2200 (2) | 0.3121 (2) | 0.38468 (8) | 0.0429 (5) | |
H63 | 0.1655 | 0.3684 | 0.4025 | 0.051* | |
C64 | 0.3237 (2) | 0.2414 (2) | 0.40938 (7) | 0.0406 (5) | |
H64 | 0.3391 | 0.2500 | 0.4438 | 0.049* | |
C65 | 0.4055 (2) | 0.15696 (19) | 0.38286 (7) | 0.0355 (4) | |
H65 | 0.4763 | 0.1100 | 0.3995 | 0.043* | |
C66 | 0.3814 (2) | 0.14289 (17) | 0.33148 (7) | 0.0298 (4) | |
H66 | 0.4356 | 0.0862 | 0.3138 | 0.036* | |
C7 | 0.45636 (19) | 0.30697 (17) | 0.23683 (6) | 0.0281 (4) | |
O2 | 0.7380 (5) | 0.4781 (5) | −0.04242 (18) | 0.0847 (15) | 0.50 |
O3 | 0.9563 (7) | 0.4577 (6) | −0.0094 (2) | 0.0918 (17) | 0.50 |
C8 | 0.8461 (7) | 0.4248 (7) | −0.0392 (3) | 0.0639 (19) | 0.50 |
C9 | 0.8777 (10) | 0.3046 (7) | −0.0676 (3) | 0.086 (2) | 0.50 |
H9A | 0.7972 | 0.2824 | −0.0890 | 0.129* | 0.50 |
H9B | 0.9595 | 0.3175 | −0.0874 | 0.129* | 0.50 |
H9C | 0.8969 | 0.2379 | −0.0440 | 0.129* | 0.50 |
C10 | 0.9363 (11) | 0.5677 (10) | 0.0207 (4) | 0.109 (3) | 0.50 |
H10A | 0.8837 | 0.5463 | 0.0496 | 0.131* | 0.50 |
H10B | 0.8827 | 0.6295 | 0.0017 | 0.131* | 0.50 |
C11 | 1.0785 (12) | 0.6199 (14) | 0.0366 (4) | 0.115 (4) | 0.50 |
H11A | 1.0649 | 0.6935 | 0.0567 | 0.173* | 0.50 |
H11B | 1.1313 | 0.5582 | 0.0559 | 0.173* | 0.50 |
H11C | 1.1303 | 0.6421 | 0.0076 | 0.173* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0290 (7) | 0.0501 (9) | 0.0345 (7) | −0.0139 (6) | 0.0001 (5) | −0.0057 (6) |
N1 | 0.0217 (6) | 0.0242 (7) | 0.0250 (7) | −0.0043 (5) | 0.0025 (5) | −0.0028 (5) |
N2 | 0.0429 (10) | 0.0480 (11) | 0.0360 (9) | −0.0228 (8) | 0.0055 (7) | −0.0085 (8) |
C2 | 0.0222 (7) | 0.0225 (8) | 0.0245 (7) | −0.0003 (6) | 0.0003 (6) | −0.0006 (6) |
C3 | 0.0214 (7) | 0.0221 (7) | 0.0249 (7) | 0.0007 (6) | −0.0007 (6) | −0.0008 (6) |
C4 | 0.0244 (8) | 0.0219 (8) | 0.0284 (8) | −0.0012 (6) | 0.0017 (6) | 0.0003 (6) |
C5 | 0.0216 (7) | 0.0203 (7) | 0.0264 (8) | −0.0004 (6) | 0.0007 (6) | 0.0006 (6) |
C6 | 0.0212 (7) | 0.0215 (7) | 0.0256 (7) | 0.0002 (6) | 0.0031 (6) | −0.0005 (6) |
C21 | 0.0262 (8) | 0.0263 (8) | 0.0251 (8) | −0.0023 (6) | 0.0036 (6) | −0.0046 (6) |
C22 | 0.0438 (11) | 0.0288 (9) | 0.0359 (10) | 0.0009 (8) | 0.0110 (8) | 0.0012 (7) |
C23 | 0.0567 (14) | 0.0377 (11) | 0.0457 (12) | −0.0075 (10) | 0.0231 (10) | 0.0007 (9) |
C24 | 0.0377 (11) | 0.0523 (13) | 0.0474 (12) | −0.0138 (10) | 0.0189 (9) | −0.0169 (10) |
C25 | 0.0246 (9) | 0.0552 (13) | 0.0409 (10) | −0.0006 (9) | 0.0009 (8) | −0.0149 (9) |
C26 | 0.0269 (9) | 0.0413 (10) | 0.0299 (9) | −0.0001 (8) | −0.0005 (7) | −0.0043 (8) |
C31 | 0.0277 (8) | 0.0264 (8) | 0.0256 (8) | −0.0039 (7) | 0.0003 (6) | −0.0017 (6) |
C32 | 0.0371 (10) | 0.0387 (10) | 0.0314 (9) | 0.0021 (8) | −0.0040 (7) | 0.0003 (8) |
C33 | 0.0563 (13) | 0.0468 (12) | 0.0310 (10) | −0.0046 (10) | −0.0114 (9) | 0.0048 (9) |
C34 | 0.0864 (19) | 0.0522 (14) | 0.0254 (9) | −0.0033 (13) | −0.0005 (11) | −0.0064 (9) |
C35 | 0.091 (2) | 0.0616 (17) | 0.0362 (12) | 0.0231 (15) | 0.0075 (12) | −0.0152 (11) |
C36 | 0.0550 (13) | 0.0459 (12) | 0.0338 (10) | 0.0181 (10) | −0.0005 (9) | −0.0081 (9) |
C51 | 0.0242 (8) | 0.0261 (8) | 0.0262 (8) | −0.0042 (6) | 0.0004 (6) | −0.0016 (6) |
C52 | 0.0298 (9) | 0.0268 (8) | 0.0325 (9) | −0.0056 (7) | −0.0014 (7) | 0.0023 (7) |
C53 | 0.0396 (10) | 0.0386 (11) | 0.0343 (9) | −0.0132 (9) | 0.0024 (8) | 0.0055 (8) |
C54 | 0.0308 (9) | 0.0517 (13) | 0.0390 (10) | −0.0113 (9) | 0.0095 (8) | 0.0007 (9) |
C55 | 0.0244 (9) | 0.0514 (12) | 0.0417 (11) | 0.0014 (8) | 0.0024 (8) | 0.0012 (9) |
C56 | 0.0271 (9) | 0.0383 (10) | 0.0317 (9) | 0.0007 (7) | 0.0016 (7) | 0.0045 (7) |
C61 | 0.0244 (8) | 0.0230 (8) | 0.0262 (8) | −0.0026 (6) | 0.0038 (6) | −0.0020 (6) |
C62 | 0.0342 (9) | 0.0323 (9) | 0.0346 (9) | 0.0040 (8) | 0.0046 (7) | −0.0054 (7) |
C63 | 0.0479 (12) | 0.0451 (12) | 0.0363 (10) | 0.0019 (10) | 0.0097 (9) | −0.0131 (9) |
C64 | 0.0493 (12) | 0.0468 (12) | 0.0258 (9) | −0.0106 (10) | 0.0037 (8) | −0.0065 (8) |
C65 | 0.0380 (10) | 0.0341 (10) | 0.0339 (9) | −0.0037 (8) | −0.0056 (8) | 0.0028 (8) |
C66 | 0.0319 (9) | 0.0272 (9) | 0.0304 (9) | 0.0001 (7) | 0.0016 (7) | −0.0020 (7) |
C7 | 0.0296 (8) | 0.0293 (9) | 0.0258 (8) | −0.0039 (7) | 0.0043 (6) | −0.0010 (7) |
O2 | 0.079 (3) | 0.098 (4) | 0.077 (3) | 0.039 (3) | 0.003 (2) | 0.004 (3) |
O3 | 0.068 (4) | 0.102 (5) | 0.106 (5) | 0.030 (3) | 0.001 (3) | 0.001 (4) |
C8 | 0.056 (3) | 0.073 (4) | 0.064 (4) | 0.025 (3) | 0.019 (3) | 0.035 (3) |
C9 | 0.104 (6) | 0.062 (4) | 0.094 (5) | 0.024 (4) | 0.020 (5) | 0.025 (4) |
C10 | 0.101 (7) | 0.109 (7) | 0.117 (7) | 0.007 (6) | 0.006 (6) | −0.007 (6) |
C11 | 0.130 (11) | 0.133 (11) | 0.083 (7) | −0.028 (9) | 0.010 (7) | 0.039 (7) |
Geometric parameters (Å, º) top
O1—C4 | 1.209 (2) | C52—H52 | 0.9300 |
N1—C7 | 1.342 (2) | C53—C54 | 1.382 (3) |
N1—C6 | 1.489 (2) | C53—H53 | 0.9300 |
N1—C2 | 1.490 (2) | C54—C55 | 1.389 (3) |
N2—C7 | 1.145 (2) | C54—H54 | 0.9300 |
C2—C21 | 1.513 (2) | C55—C56 | 1.390 (3) |
C2—C3 | 1.553 (2) | C55—H55 | 0.9300 |
C2—H2 | 0.9800 | C56—H56 | 0.9300 |
C3—C31 | 1.512 (2) | C61—C62 | 1.392 (2) |
C3—C4 | 1.526 (2) | C61—C66 | 1.392 (3) |
C3—H3 | 0.9800 | C62—C63 | 1.388 (3) |
C4—C5 | 1.521 (2) | C62—H62 | 0.9300 |
C5—C51 | 1.512 (2) | C63—C64 | 1.378 (3) |
C5—C6 | 1.556 (2) | C63—H63 | 0.9300 |
C5—H5 | 0.9800 | C64—C65 | 1.393 (3) |
C6—C61 | 1.514 (2) | C64—H64 | 0.9300 |
C6—H6 | 0.9800 | C65—C66 | 1.391 (3) |
C21—C26 | 1.393 (3) | C65—H65 | 0.9300 |
C21—C22 | 1.394 (3) | C66—H66 | 0.9300 |
C22—C23 | 1.392 (3) | O2—C8 | 1.162 (7) |
C22—H22 | 0.9300 | O3—C10i | 1.098 (10) |
C23—C24 | 1.376 (4) | O3—C11i | 1.139 (14) |
C23—H23 | 0.9300 | O3—O3i | 1.303 (14) |
C24—C25 | 1.388 (4) | O3—C8 | 1.328 (11) |
C24—H24 | 0.9300 | O3—C10 | 1.434 (12) |
C25—C26 | 1.394 (3) | C8—C11i | 0.853 (13) |
C25—H25 | 0.9300 | C8—C9 | 1.521 (12) |
C26—H26 | 0.9300 | C9—C11i | 1.214 (15) |
C31—C36 | 1.382 (3) | C9—H9A | 0.9600 |
C31—C32 | 1.389 (3) | C9—H9B | 0.9599 |
C32—C33 | 1.391 (3) | C9—H9C | 0.9600 |
C32—H32 | 0.9300 | C10—O3i | 1.098 (10) |
C33—C34 | 1.373 (4) | C10—C11 | 1.492 (9) |
C33—H33 | 0.9300 | C10—H10A | 0.9599 |
C34—C35 | 1.368 (4) | C10—H10B | 0.9599 |
C34—H34 | 0.9300 | C11—C8i | 0.853 (13) |
C35—C36 | 1.391 (3) | C11—O3i | 1.139 (14) |
C35—H35 | 0.9300 | C11—C9i | 1.214 (15) |
C36—H36 | 0.9300 | C11—H11A | 0.9601 |
C51—C52 | 1.392 (2) | C11—H11B | 0.9601 |
C51—C56 | 1.393 (3) | C11—H11C | 0.9600 |
C52—C53 | 1.389 (3) | | |
| | | |
C7—N1—C6 | 114.26 (13) | C31—C36—C35 | 120.3 (2) |
C7—N1—C2 | 115.44 (13) | C31—C36—H36 | 119.9 |
C6—N1—C2 | 116.36 (13) | C35—C36—H36 | 119.9 |
N1—C2—C21 | 110.59 (13) | C52—C51—C56 | 118.88 (16) |
N1—C2—C3 | 108.17 (13) | C52—C51—C5 | 119.26 (16) |
C21—C2—C3 | 111.72 (13) | C56—C51—C5 | 121.77 (16) |
N1—C2—H2 | 108.8 | C53—C52—C51 | 120.36 (18) |
C21—C2—H2 | 108.8 | C53—C52—H52 | 119.8 |
C3—C2—H2 | 108.8 | C51—C52—H52 | 119.8 |
C31—C3—C4 | 113.82 (14) | C54—C53—C52 | 120.48 (18) |
C31—C3—C2 | 110.99 (14) | C54—C53—H53 | 119.8 |
C4—C3—C2 | 109.04 (13) | C52—C53—H53 | 119.8 |
C31—C3—H3 | 107.6 | C53—C54—C55 | 119.65 (18) |
C4—C3—H3 | 107.6 | C53—C54—H54 | 120.2 |
C2—C3—H3 | 107.6 | C55—C54—H54 | 120.2 |
O1—C4—C5 | 123.26 (15) | C54—C55—C56 | 119.96 (19) |
O1—C4—C3 | 122.81 (15) | C54—C55—H55 | 120.0 |
C5—C4—C3 | 113.92 (13) | C56—C55—H55 | 120.0 |
C51—C5—C4 | 114.56 (13) | C55—C56—C51 | 120.67 (18) |
C51—C5—C6 | 110.19 (13) | C55—C56—H56 | 119.7 |
C4—C5—C6 | 109.95 (13) | C51—C56—H56 | 119.7 |
C51—C5—H5 | 107.3 | C62—C61—C66 | 119.70 (16) |
C4—C5—H5 | 107.3 | C62—C61—C6 | 118.99 (16) |
C6—C5—H5 | 107.3 | C66—C61—C6 | 121.26 (15) |
N1—C6—C61 | 110.61 (13) | C63—C62—C61 | 120.13 (19) |
N1—C6—C5 | 108.82 (13) | C63—C62—H62 | 119.9 |
C61—C6—C5 | 110.47 (13) | C61—C62—H62 | 119.9 |
N1—C6—H6 | 109.0 | C64—C63—C62 | 120.21 (19) |
C61—C6—H6 | 109.0 | C64—C63—H63 | 119.9 |
C5—C6—H6 | 109.0 | C62—C63—H63 | 119.9 |
C26—C21—C22 | 119.38 (17) | C63—C64—C65 | 120.07 (18) |
C26—C21—C2 | 121.00 (16) | C63—C64—H64 | 120.0 |
C22—C21—C2 | 119.61 (16) | C65—C64—H64 | 120.0 |
C23—C22—C21 | 120.0 (2) | C66—C65—C64 | 119.99 (19) |
C23—C22—H22 | 120.0 | C66—C65—H65 | 120.0 |
C21—C22—H22 | 120.0 | C64—C65—H65 | 120.0 |
C24—C23—C22 | 120.4 (2) | C65—C66—C61 | 119.88 (17) |
C24—C23—H23 | 119.8 | C65—C66—H66 | 120.1 |
C22—C23—H23 | 119.8 | C61—C66—H66 | 120.1 |
C23—C24—C25 | 120.24 (19) | N2—C7—N1 | 176.6 (2) |
C23—C24—H24 | 119.9 | C8—O3—C10 | 115.7 (7) |
C25—C24—H24 | 119.9 | O2—C8—O3 | 125.1 (8) |
C24—C25—C26 | 119.8 (2) | O2—C8—C9 | 123.9 (8) |
C24—C25—H25 | 120.1 | O3—C8—C9 | 111.0 (6) |
C26—C25—H25 | 120.1 | C8—C9—H9A | 109.9 |
C21—C26—C25 | 120.23 (19) | C8—C9—H9B | 109.3 |
C21—C26—H26 | 119.9 | H9A—C9—H9B | 109.5 |
C25—C26—H26 | 119.9 | C8—C9—H9C | 109.2 |
C36—C31—C32 | 118.79 (17) | H9A—C9—H9C | 109.5 |
C36—C31—C3 | 119.46 (16) | H9B—C9—H9C | 109.5 |
C32—C31—C3 | 121.74 (16) | O3—C10—C11 | 109.1 (11) |
C31—C32—C33 | 120.4 (2) | O3—C10—H10A | 109.9 |
C31—C32—H32 | 119.8 | C11—C10—H10A | 110.0 |
C33—C32—H32 | 119.8 | O3—C10—H10B | 109.8 |
C34—C33—C32 | 120.1 (2) | C11—C10—H10B | 109.9 |
C34—C33—H33 | 120.0 | H10A—C10—H10B | 108.2 |
C32—C33—H33 | 120.0 | C10—C11—H11A | 108.9 |
C35—C34—C33 | 120.0 (2) | C10—C11—H11B | 109.7 |
C35—C34—H34 | 120.0 | H11A—C11—H11B | 109.5 |
C33—C34—H34 | 120.0 | C10—C11—H11C | 109.8 |
C34—C35—C36 | 120.5 (2) | H11A—C11—H11C | 109.5 |
C34—C35—H35 | 119.7 | H11B—C11—H11C | 109.5 |
C36—C35—H35 | 119.7 | | |
| | | |
C7—N1—C2—C21 | 40.0 (2) | C2—C3—C31—C32 | −66.5 (2) |
C6—N1—C2—C21 | 178.07 (14) | C36—C31—C32—C33 | −0.5 (3) |
C7—N1—C2—C3 | 162.67 (14) | C3—C31—C32—C33 | 178.20 (18) |
C6—N1—C2—C3 | −59.28 (17) | C31—C32—C33—C34 | 0.2 (3) |
N1—C2—C3—C31 | −178.71 (13) | C32—C33—C34—C35 | −0.1 (4) |
C21—C2—C3—C31 | −56.75 (18) | C33—C34—C35—C36 | 0.1 (5) |
N1—C2—C3—C4 | 55.14 (16) | C32—C31—C36—C35 | 0.5 (4) |
C21—C2—C3—C4 | 177.10 (13) | C3—C31—C36—C35 | −178.2 (2) |
C31—C3—C4—O1 | −0.5 (2) | C34—C35—C36—C31 | −0.3 (5) |
C2—C3—C4—O1 | 124.05 (18) | C4—C5—C51—C52 | 125.65 (17) |
C31—C3—C4—C5 | 178.70 (14) | C6—C5—C51—C52 | −109.76 (18) |
C2—C3—C4—C5 | −56.80 (18) | C4—C5—C51—C56 | −57.9 (2) |
O1—C4—C5—C51 | −1.0 (2) | C6—C5—C51—C56 | 66.7 (2) |
C3—C4—C5—C51 | 179.87 (14) | C56—C51—C52—C53 | 0.0 (3) |
O1—C4—C5—C6 | −125.70 (18) | C5—C51—C52—C53 | 176.58 (16) |
C3—C4—C5—C6 | 55.15 (18) | C51—C52—C53—C54 | 0.7 (3) |
C7—N1—C6—C61 | −42.45 (19) | C52—C53—C54—C55 | −1.0 (3) |
C2—N1—C6—C61 | 179.02 (13) | C53—C54—C55—C56 | 0.5 (3) |
C7—N1—C6—C5 | −163.98 (14) | C54—C55—C56—C51 | 0.2 (3) |
C2—N1—C6—C5 | 57.49 (18) | C52—C51—C56—C55 | −0.5 (3) |
C51—C5—C6—N1 | −179.14 (13) | C5—C51—C56—C55 | −176.94 (18) |
C4—C5—C6—N1 | −51.94 (17) | N1—C6—C61—C62 | 127.54 (17) |
C51—C5—C6—C61 | 59.25 (17) | C5—C6—C61—C62 | −111.91 (18) |
C4—C5—C6—C61 | −173.55 (13) | N1—C6—C61—C66 | −54.9 (2) |
N1—C2—C21—C26 | 56.7 (2) | C5—C6—C61—C66 | 65.7 (2) |
C3—C2—C21—C26 | −63.9 (2) | C66—C61—C62—C63 | −1.6 (3) |
N1—C2—C21—C22 | −124.17 (17) | C6—C61—C62—C63 | 175.97 (18) |
C3—C2—C21—C22 | 115.27 (18) | C61—C62—C63—C64 | 1.3 (3) |
C26—C21—C22—C23 | −0.1 (3) | C62—C63—C64—C65 | 0.0 (3) |
C2—C21—C22—C23 | −179.22 (18) | C63—C64—C65—C66 | −0.8 (3) |
C21—C22—C23—C24 | −0.6 (3) | C64—C65—C66—C61 | 0.4 (3) |
C22—C23—C24—C25 | 1.1 (3) | C62—C61—C66—C65 | 0.8 (3) |
C23—C24—C25—C26 | −0.8 (3) | C6—C61—C66—C65 | −176.74 (16) |
C22—C21—C26—C25 | 0.3 (3) | C6—N1—C7—N2 | 91 (3) |
C2—C21—C26—C25 | 179.45 (17) | C2—N1—C7—N2 | −130 (3) |
C24—C25—C26—C21 | 0.1 (3) | C10—O3—C8—O2 | 0.1 (11) |
C4—C3—C31—C36 | −124.4 (2) | C10—O3—C8—C9 | −177.8 (7) |
C2—C3—C31—C36 | 112.2 (2) | C8—O3—C10—C11 | −158.9 (8) |
C4—C3—C31—C32 | 57.0 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N2ii | 0.98 | 2.57 | 3.433 (2) | 147 |
C5—H5···N2ii | 0.98 | 2.42 | 3.317 (2) | 152 |
C25—H25···O1iii | 0.93 | 2.47 | 3.399 (3) | 176 |
C62—H62···O1iv | 0.93 | 2.44 | 3.203 (2) | 139 |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x+1, y, z; (iv) −x, y+1/2, −z+1/2. |