organic compounds
There are two independent molecules in the asymmetric unit of the title N-substituted oxindole, C22H26N2O2, which was obtained unexpectedly. The heterocyclic rings in both molecules adopt N-envelope conformations and the isoindole ring systems are essentially planar.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002085/lh2289sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002085/lh22894bsup2.hkl |
CCDC reference: 636745
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.145
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.143 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.20 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H4C .. H4C .. 2.14 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5-methyl-1-(3,3,5-trimethyl-2-p-tolyl-1,2-oxazolidin-5-yl)-1H-indol-3(2H)-one top
Crystal data top
C22H26N2O2 | F(000) = 1504 |
Mr = 350.45 | Dx = 1.206 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 32322 reflections |
a = 19.390 (3) Å | θ = 2.8–27.4° |
b = 14.037 (3) Å | µ = 0.08 mm−1 |
c = 14.266 (5) Å | T = 173 K |
β = 96.057 (8)° | Block, colorless |
V = 3861.2 (17) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 8 |
Data collection top
Nonius KappaCCD diffractometer | 8752 independent reflections |
Radiation source: fine-focus sealed tube | 3897 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.143 |
ω and φ scans | θmax = 27.4°, θmin = 2.8° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −25→25 |
Tmin = 0.982, Tmax = 0.986 | k = −18→18 |
32322 measured reflections | l = −17→18 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
8752 reflections | (Δ/σ)max = 0.001 |
479 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.44225 (7) | 0.62775 (11) | 0.83886 (9) | 0.0444 (4) | |
O2 | 0.25011 (7) | 0.50396 (11) | 0.88091 (9) | 0.0445 (4) | |
N1 | 0.43897 (9) | 0.61052 (12) | 0.73666 (11) | 0.0372 (5) | |
N2 | 0.32321 (8) | 0.63167 (13) | 0.86456 (10) | 0.0345 (4) | |
C1 | 0.38682 (11) | 0.57223 (16) | 0.86811 (14) | 0.0411 (6) | |
C2 | 0.37772 (12) | 0.49014 (16) | 0.79706 (14) | 0.0444 (6) | |
H2A | 0.3821 | 0.4279 | 0.8297 | 0.053* | |
H2B | 0.3318 | 0.4935 | 0.7597 | 0.053* | |
C3 | 0.43595 (12) | 0.50368 (15) | 0.73392 (14) | 0.0422 (6) | |
C4 | 0.40759 (12) | 0.5441 (2) | 0.96945 (14) | 0.0620 (8) | |
H4A | 0.3682 | 0.5138 | 0.9953 | 0.074* | |
H4B | 0.4216 | 0.6009 | 1.0065 | 0.074* | |
H4C | 0.4465 | 0.4992 | 0.9723 | 0.074* | |
C5 | 0.41468 (13) | 0.47047 (17) | 0.63323 (14) | 0.0555 (7) | |
H5A | 0.4055 | 0.4018 | 0.6331 | 0.067* | |
H5B | 0.4522 | 0.4839 | 0.5942 | 0.067* | |
H5C | 0.3726 | 0.5044 | 0.6077 | 0.067* | |
C6 | 0.50321 (12) | 0.45589 (18) | 0.77373 (16) | 0.0562 (7) | |
H6A | 0.4960 | 0.3869 | 0.7773 | 0.067* | |
H6B | 0.5175 | 0.4809 | 0.8370 | 0.067* | |
H6C | 0.5395 | 0.4691 | 0.7326 | 0.067* | |
C7 | 0.49840 (12) | 0.65435 (16) | 0.70256 (15) | 0.0431 (6) | |
C8 | 0.49241 (14) | 0.67518 (17) | 0.60675 (16) | 0.0556 (7) | |
H8A | 0.4499 | 0.6632 | 0.5691 | 0.067* | |
C9 | 0.54760 (17) | 0.71301 (19) | 0.5661 (2) | 0.0695 (8) | |
H9A | 0.5427 | 0.7256 | 0.5003 | 0.083* | |
C10 | 0.60921 (17) | 0.73297 (19) | 0.6179 (2) | 0.0698 (9) | |
C11 | 0.61402 (14) | 0.71581 (18) | 0.7149 (2) | 0.0672 (8) | |
H11A | 0.6557 | 0.7317 | 0.7528 | 0.081* | |
C12 | 0.55934 (12) | 0.67598 (17) | 0.75749 (18) | 0.0534 (7) | |
H12A | 0.5639 | 0.6639 | 0.8234 | 0.064* | |
C13 | 0.25987 (11) | 0.58980 (17) | 0.87571 (12) | 0.0342 (5) | |
C14 | 0.20735 (10) | 0.66829 (14) | 0.88163 (13) | 0.0336 (5) | |
H14A | 0.1706 | 0.6651 | 0.8279 | 0.040* | |
H14B | 0.1856 | 0.6643 | 0.9412 | 0.040* | |
C15 | 0.24879 (11) | 0.75707 (15) | 0.87804 (12) | 0.0314 (5) | |
C16 | 0.22894 (12) | 0.85102 (16) | 0.88018 (12) | 0.0383 (6) | |
H16A | 0.1814 | 0.8666 | 0.8818 | 0.046* | |
C17 | 0.27795 (13) | 0.92347 (16) | 0.87994 (14) | 0.0444 (6) | |
C18 | 0.34625 (13) | 0.89743 (17) | 0.87672 (14) | 0.0491 (6) | |
H18A | 0.3803 | 0.9463 | 0.8783 | 0.059* | |
C19 | 0.36791 (12) | 0.80311 (17) | 0.87121 (14) | 0.0455 (6) | |
H19A | 0.4152 | 0.7877 | 0.8672 | 0.055* | |
C20 | 0.31786 (11) | 0.73262 (16) | 0.87172 (12) | 0.0345 (5) | |
C21 | 0.67054 (17) | 0.7724 (2) | 0.5720 (2) | 0.1019 (12) | |
H21A | 0.7063 | 0.7942 | 0.6210 | 0.122* | |
H21B | 0.6551 | 0.8260 | 0.5311 | 0.122* | |
H21C | 0.6897 | 0.7224 | 0.5344 | 0.122* | |
C22 | 0.25677 (14) | 1.02618 (17) | 0.88451 (16) | 0.0624 (7) | |
H22A | 0.2904 | 1.0661 | 0.8560 | 0.075* | |
H22B | 0.2554 | 1.0448 | 0.9505 | 0.075* | |
H22C | 0.2107 | 1.0346 | 0.8501 | 0.075* | |
O1' | 0.04778 (7) | 0.66518 (9) | 0.66785 (8) | 0.0344 (4) | |
O2' | 0.23338 (7) | 0.52758 (11) | 0.61424 (9) | 0.0418 (4) | |
N1' | 0.04802 (8) | 0.63046 (12) | 0.76539 (10) | 0.0321 (4) | |
N2' | 0.16636 (8) | 0.65966 (11) | 0.63872 (10) | 0.0286 (4) | |
C1' | 0.09873 (10) | 0.60879 (15) | 0.62836 (13) | 0.0321 (5) | |
C2' | 0.10210 (11) | 0.51568 (15) | 0.68555 (13) | 0.0371 (5) | |
H2C | 0.0939 | 0.4599 | 0.6434 | 0.045* | |
H2D | 0.1479 | 0.5086 | 0.7227 | 0.045* | |
C3' | 0.04472 (11) | 0.52487 (15) | 0.75030 (13) | 0.0347 (5) | |
C4' | 0.07507 (11) | 0.59882 (16) | 0.52427 (12) | 0.0430 (6) | |
H4D | 0.1074 | 0.5576 | 0.4948 | 0.052* | |
H4E | 0.0739 | 0.6618 | 0.4944 | 0.052* | |
H4F | 0.0286 | 0.5706 | 0.5161 | 0.052* | |
C6' | −0.02510 (11) | 0.49005 (16) | 0.70353 (14) | 0.0438 (6) | |
H6D | −0.0221 | 0.4220 | 0.6893 | 0.053* | |
H6E | −0.0373 | 0.5255 | 0.6450 | 0.053* | |
H6F | −0.0608 | 0.5003 | 0.7463 | 0.053* | |
C5' | 0.06274 (12) | 0.47386 (16) | 0.84412 (13) | 0.0453 (6) | |
H5D | 0.0671 | 0.4054 | 0.8329 | 0.054* | |
H5E | 0.0259 | 0.4849 | 0.8849 | 0.054* | |
H5F | 0.1067 | 0.4986 | 0.8748 | 0.054* | |
C7' | −0.00959 (11) | 0.67316 (14) | 0.80430 (14) | 0.0344 (5) | |
C8' | −0.00602 (13) | 0.67675 (16) | 0.90212 (14) | 0.0473 (6) | |
H8B | 0.0338 | 0.6528 | 0.9392 | 0.057* | |
C9' | −0.05983 (15) | 0.71484 (19) | 0.94553 (18) | 0.0600 (7) | |
H9B | −0.0575 | 0.7139 | 1.0124 | 0.072* | |
C10' | −0.11647 (15) | 0.75392 (17) | 0.89506 (19) | 0.0568 (7) | |
C11' | −0.11992 (13) | 0.75240 (17) | 0.79699 (18) | 0.0556 (7) | |
H11B | −0.1589 | 0.7794 | 0.7606 | 0.067* | |
C12' | −0.06666 (12) | 0.71158 (16) | 0.75165 (16) | 0.0442 (6) | |
H12B | −0.0697 | 0.7103 | 0.6848 | 0.053* | |
C13' | 0.22753 (11) | 0.61367 (16) | 0.62476 (13) | 0.0323 (5) | |
C14' | 0.28425 (10) | 0.68730 (14) | 0.62381 (13) | 0.0320 (5) | |
H14C | 0.3192 | 0.6801 | 0.6792 | 0.038* | |
H14D | 0.3077 | 0.6825 | 0.5656 | 0.038* | |
C15' | 0.24614 (10) | 0.77932 (14) | 0.62739 (12) | 0.0288 (5) | |
C16' | 0.26977 (11) | 0.87179 (15) | 0.62464 (12) | 0.0344 (5) | |
H16B | 0.3179 | 0.8840 | 0.6242 | 0.041* | |
C17' | 0.22291 (12) | 0.94767 (15) | 0.62250 (13) | 0.0364 (5) | |
C18' | 0.15322 (11) | 0.92652 (15) | 0.62377 (13) | 0.0388 (6) | |
H18B | 0.1209 | 0.9776 | 0.6202 | 0.047* | |
C19' | 0.12823 (11) | 0.83401 (14) | 0.63003 (13) | 0.0344 (5) | |
H19B | 0.0803 | 0.8219 | 0.6328 | 0.041* | |
C20' | 0.17579 (10) | 0.76044 (14) | 0.63208 (12) | 0.0274 (5) | |
C21' | −0.17547 (15) | 0.79733 (19) | 0.9430 (2) | 0.0816 (10) | |
H21D | −0.1923 | 0.7507 | 0.9864 | 0.098* | |
H21E | −0.2134 | 0.8151 | 0.8952 | 0.098* | |
H21F | −0.1588 | 0.8542 | 0.9783 | 0.098* | |
C22' | 0.24768 (13) | 1.04884 (16) | 0.61666 (16) | 0.0532 (7) | |
H22D | 0.2174 | 1.0910 | 0.6487 | 0.064* | |
H22E | 0.2465 | 1.0677 | 0.5504 | 0.064* | |
H22F | 0.2953 | 1.0538 | 0.6471 | 0.064* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0320 (9) | 0.0660 (11) | 0.0367 (8) | 0.0038 (8) | 0.0113 (7) | −0.0083 (7) |
O2 | 0.0445 (10) | 0.0419 (11) | 0.0495 (9) | 0.0037 (8) | 0.0161 (7) | 0.0014 (7) |
N1 | 0.0376 (11) | 0.0456 (12) | 0.0304 (10) | 0.0056 (9) | 0.0131 (8) | −0.0012 (8) |
N2 | 0.0284 (11) | 0.0441 (12) | 0.0317 (9) | 0.0065 (9) | 0.0070 (7) | −0.0044 (8) |
C1 | 0.0302 (13) | 0.0587 (16) | 0.0362 (12) | 0.0085 (12) | 0.0123 (10) | 0.0051 (11) |
C2 | 0.0454 (14) | 0.0440 (15) | 0.0467 (13) | 0.0115 (12) | 0.0194 (11) | 0.0066 (11) |
C3 | 0.0471 (15) | 0.0375 (15) | 0.0453 (13) | 0.0122 (12) | 0.0198 (11) | 0.0053 (10) |
C4 | 0.0400 (15) | 0.107 (2) | 0.0399 (14) | 0.0226 (15) | 0.0079 (11) | 0.0138 (13) |
C5 | 0.0683 (18) | 0.0484 (16) | 0.0542 (15) | 0.0046 (14) | 0.0265 (13) | −0.0087 (12) |
C6 | 0.0520 (17) | 0.0579 (17) | 0.0636 (15) | 0.0226 (14) | 0.0293 (13) | 0.0147 (13) |
C7 | 0.0408 (15) | 0.0391 (15) | 0.0524 (14) | 0.0093 (12) | 0.0192 (11) | −0.0005 (11) |
C8 | 0.0647 (19) | 0.0528 (17) | 0.0538 (16) | 0.0045 (14) | 0.0263 (13) | 0.0059 (12) |
C9 | 0.088 (2) | 0.0553 (19) | 0.0736 (19) | 0.0042 (17) | 0.0474 (18) | 0.0051 (14) |
C10 | 0.074 (2) | 0.0400 (17) | 0.107 (2) | 0.0085 (16) | 0.061 (2) | 0.0056 (16) |
C11 | 0.0434 (17) | 0.0509 (18) | 0.112 (2) | 0.0011 (14) | 0.0284 (16) | −0.0053 (16) |
C12 | 0.0376 (15) | 0.0550 (17) | 0.0702 (17) | 0.0065 (13) | 0.0181 (13) | 0.0002 (13) |
C13 | 0.0325 (13) | 0.0464 (16) | 0.0243 (11) | 0.0022 (11) | 0.0064 (9) | −0.0020 (10) |
C14 | 0.0296 (12) | 0.0467 (15) | 0.0250 (11) | 0.0043 (11) | 0.0053 (9) | −0.0041 (9) |
C15 | 0.0325 (13) | 0.0419 (15) | 0.0208 (10) | 0.0031 (11) | 0.0072 (9) | −0.0006 (9) |
C16 | 0.0433 (14) | 0.0470 (16) | 0.0262 (11) | 0.0062 (12) | 0.0111 (10) | 0.0002 (10) |
C17 | 0.0588 (17) | 0.0435 (16) | 0.0345 (12) | 0.0009 (13) | 0.0219 (11) | −0.0013 (10) |
C18 | 0.0589 (18) | 0.0493 (17) | 0.0431 (14) | −0.0138 (14) | 0.0245 (12) | −0.0076 (11) |
C19 | 0.0396 (15) | 0.0590 (18) | 0.0403 (13) | −0.0041 (13) | 0.0151 (11) | −0.0077 (11) |
C20 | 0.0338 (13) | 0.0459 (15) | 0.0250 (11) | 0.0012 (11) | 0.0082 (9) | −0.0043 (9) |
C21 | 0.097 (3) | 0.053 (2) | 0.172 (3) | 0.0007 (18) | 0.095 (2) | 0.001 (2) |
C22 | 0.086 (2) | 0.0483 (17) | 0.0597 (15) | −0.0018 (15) | 0.0368 (14) | 0.0022 (13) |
O1' | 0.0359 (9) | 0.0395 (9) | 0.0294 (7) | −0.0017 (7) | 0.0115 (6) | 0.0044 (6) |
O2' | 0.0466 (10) | 0.0330 (10) | 0.0487 (9) | 0.0004 (8) | 0.0185 (7) | −0.0012 (7) |
N1' | 0.0371 (11) | 0.0343 (11) | 0.0263 (9) | −0.0045 (8) | 0.0104 (7) | 0.0002 (7) |
N2' | 0.0303 (10) | 0.0285 (11) | 0.0282 (9) | −0.0048 (8) | 0.0081 (7) | −0.0014 (7) |
C1' | 0.0310 (12) | 0.0358 (13) | 0.0312 (11) | −0.0040 (10) | 0.0108 (9) | −0.0034 (9) |
C2' | 0.0437 (14) | 0.0336 (13) | 0.0363 (11) | −0.0068 (11) | 0.0151 (10) | −0.0025 (9) |
C3' | 0.0409 (13) | 0.0318 (13) | 0.0327 (11) | −0.0073 (10) | 0.0102 (9) | −0.0011 (9) |
C4' | 0.0456 (15) | 0.0536 (16) | 0.0306 (12) | −0.0133 (12) | 0.0079 (10) | −0.0065 (10) |
C6' | 0.0485 (15) | 0.0450 (15) | 0.0405 (12) | −0.0152 (12) | 0.0164 (10) | −0.0064 (10) |
C5' | 0.0578 (16) | 0.0404 (14) | 0.0403 (12) | −0.0048 (12) | 0.0176 (11) | 0.0046 (10) |
C7' | 0.0368 (13) | 0.0316 (13) | 0.0365 (12) | −0.0062 (11) | 0.0115 (10) | −0.0032 (9) |
C8' | 0.0579 (16) | 0.0487 (16) | 0.0378 (13) | −0.0066 (13) | 0.0166 (11) | −0.0090 (11) |
C9' | 0.081 (2) | 0.0552 (18) | 0.0496 (15) | −0.0041 (16) | 0.0328 (15) | −0.0090 (12) |
C10' | 0.070 (2) | 0.0343 (15) | 0.0750 (19) | −0.0071 (14) | 0.0476 (16) | −0.0053 (13) |
C11' | 0.0451 (16) | 0.0458 (17) | 0.0789 (19) | 0.0032 (13) | 0.0208 (13) | 0.0073 (13) |
C12' | 0.0441 (15) | 0.0431 (15) | 0.0481 (14) | −0.0015 (12) | 0.0177 (12) | 0.0035 (11) |
C13' | 0.0379 (14) | 0.0345 (14) | 0.0259 (11) | 0.0007 (11) | 0.0101 (9) | 0.0011 (9) |
C14' | 0.0306 (12) | 0.0413 (14) | 0.0250 (11) | −0.0013 (10) | 0.0064 (9) | 0.0025 (9) |
C15' | 0.0317 (13) | 0.0346 (14) | 0.0204 (10) | −0.0028 (10) | 0.0045 (8) | 0.0005 (8) |
C16' | 0.0370 (13) | 0.0397 (15) | 0.0277 (11) | −0.0087 (11) | 0.0094 (9) | −0.0025 (9) |
C17' | 0.0479 (15) | 0.0302 (13) | 0.0334 (12) | −0.0044 (12) | 0.0155 (10) | −0.0030 (9) |
C18' | 0.0428 (15) | 0.0338 (14) | 0.0421 (13) | 0.0034 (11) | 0.0155 (10) | 0.0002 (10) |
C19' | 0.0337 (13) | 0.0361 (14) | 0.0352 (12) | −0.0017 (11) | 0.0117 (9) | −0.0003 (9) |
C20' | 0.0319 (13) | 0.0308 (13) | 0.0202 (10) | −0.0026 (10) | 0.0055 (8) | −0.0005 (8) |
C21' | 0.091 (2) | 0.0499 (18) | 0.117 (2) | 0.0037 (17) | 0.071 (2) | −0.0021 (16) |
C22' | 0.0627 (17) | 0.0409 (15) | 0.0608 (15) | −0.0079 (13) | 0.0282 (13) | −0.0058 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.425 (2) | O1'—C1' | 1.427 (2) |
O1—N1 | 1.473 (2) | O1'—N1' | 1.474 (2) |
O2—C13 | 1.223 (2) | O2'—C13' | 1.224 (2) |
N1—C7 | 1.436 (3) | N1'—C7' | 1.430 (2) |
N1—C3 | 1.501 (3) | N1'—C3' | 1.498 (3) |
N2—C13 | 1.386 (3) | N2'—C13' | 1.383 (2) |
N2—C20 | 1.425 (3) | N2'—C20' | 1.431 (2) |
N2—C1 | 1.486 (3) | N2'—C1' | 1.487 (2) |
C1—C4 | 1.512 (3) | C1'—C4' | 1.514 (3) |
C1—C2 | 1.532 (3) | C1'—C2' | 1.539 (3) |
C2—C3 | 1.529 (3) | C2'—C3' | 1.525 (3) |
C2—H2A | 0.9900 | C2'—H2C | 0.9900 |
C2—H2B | 0.9900 | C2'—H2D | 0.9900 |
C3—C6 | 1.522 (3) | C3'—C6' | 1.525 (3) |
C3—C5 | 1.525 (3) | C3'—C5' | 1.526 (3) |
C4—H4A | 0.9800 | C4'—H4D | 0.9800 |
C4—H4B | 0.9800 | C4'—H4E | 0.9800 |
C4—H4C | 0.9800 | C4'—H4F | 0.9800 |
C5—H5A | 0.9800 | C6'—H6D | 0.9800 |
C5—H5B | 0.9800 | C6'—H6E | 0.9800 |
C5—H5C | 0.9800 | C6'—H6F | 0.9800 |
C6—H6A | 0.9800 | C5'—H5D | 0.9800 |
C6—H6B | 0.9800 | C5'—H5E | 0.9800 |
C6—H6C | 0.9800 | C5'—H5F | 0.9800 |
C7—C12 | 1.381 (3) | C7'—C12' | 1.380 (3) |
C7—C8 | 1.391 (3) | C7'—C8' | 1.391 (3) |
C8—C9 | 1.376 (3) | C8'—C9' | 1.376 (3) |
C8—H8A | 0.9500 | C8'—H8B | 0.9500 |
C9—C10 | 1.366 (4) | C9'—C10' | 1.363 (4) |
C9—H9A | 0.9500 | C9'—H9B | 0.9500 |
C10—C11 | 1.397 (4) | C10'—C11' | 1.394 (3) |
C10—C21 | 1.521 (3) | C10'—C21' | 1.521 (3) |
C11—C12 | 1.394 (3) | C11'—C12' | 1.398 (3) |
C11—H11A | 0.9500 | C11'—H11B | 0.9500 |
C12—H12A | 0.9500 | C12'—H12B | 0.9500 |
C13—C14 | 1.509 (3) | C13'—C14' | 1.510 (3) |
C14—C15 | 1.487 (3) | C14'—C15' | 1.492 (3) |
C14—H14A | 0.9900 | C14'—H14C | 0.9900 |
C14—H14B | 0.9900 | C14'—H14D | 0.9900 |
C15—C16 | 1.375 (3) | C15'—C16' | 1.378 (3) |
C15—C20 | 1.395 (3) | C15'—C20' | 1.398 (3) |
C16—C17 | 1.392 (3) | C16'—C17' | 1.398 (3) |
C16—H16A | 0.9500 | C16'—H16B | 0.9500 |
C17—C18 | 1.379 (3) | C17'—C18' | 1.385 (3) |
C17—C22 | 1.502 (3) | C17'—C22' | 1.504 (3) |
C18—C19 | 1.394 (3) | C18'—C19' | 1.392 (3) |
C18—H18A | 0.9500 | C18'—H18B | 0.9500 |
C19—C20 | 1.386 (3) | C19'—C20' | 1.383 (3) |
C19—H19A | 0.9500 | C19'—H19B | 0.9500 |
C21—H21A | 0.9800 | C21'—H21D | 0.9800 |
C21—H21B | 0.9800 | C21'—H21E | 0.9800 |
C21—H21C | 0.9800 | C21'—H21F | 0.9800 |
C22—H22A | 0.9800 | C22'—H22D | 0.9800 |
C22—H22B | 0.9800 | C22'—H22E | 0.9800 |
C22—H22C | 0.9800 | C22'—H22F | 0.9800 |
C1—O1—N1 | 104.18 (14) | C1'—O1'—N1' | 104.82 (13) |
C7—N1—O1 | 108.22 (15) | C7'—N1'—O1' | 107.64 (14) |
C7—N1—C3 | 116.73 (16) | C7'—N1'—C3' | 116.56 (16) |
O1—N1—C3 | 100.80 (14) | O1'—N1'—C3' | 101.29 (12) |
C13—N2—C20 | 109.96 (17) | C13'—N2'—C20' | 109.53 (16) |
C13—N2—C1 | 120.04 (18) | C13'—N2'—C1' | 121.49 (17) |
C20—N2—C1 | 128.49 (18) | C20'—N2'—C1' | 125.86 (16) |
O1—C1—N2 | 109.38 (17) | O1'—C1'—N2' | 109.53 (15) |
O1—C1—C4 | 106.86 (17) | O1'—C1'—C4' | 106.72 (16) |
N2—C1—C4 | 108.42 (16) | N2'—C1'—C4' | 108.35 (15) |
O1—C1—C2 | 104.79 (16) | O1'—C1'—C2' | 104.73 (15) |
N2—C1—C2 | 111.26 (17) | N2'—C1'—C2' | 111.57 (16) |
C4—C1—C2 | 115.9 (2) | C4'—C1'—C2' | 115.67 (17) |
C3—C2—C1 | 104.81 (18) | C3'—C2'—C1' | 104.86 (16) |
C3—C2—H2A | 110.8 | C3'—C2'—H2C | 110.8 |
C1—C2—H2A | 110.8 | C1'—C2'—H2C | 110.8 |
C3—C2—H2B | 110.8 | C3'—C2'—H2D | 110.8 |
C1—C2—H2B | 110.8 | C1'—C2'—H2D | 110.8 |
H2A—C2—H2B | 108.9 | H2C—C2'—H2D | 108.8 |
N1—C3—C6 | 113.64 (19) | N1'—C3'—C2' | 98.51 (15) |
N1—C3—C5 | 109.62 (17) | N1'—C3'—C6' | 113.73 (18) |
C6—C3—C5 | 110.65 (18) | C2'—C3'—C6' | 112.25 (17) |
N1—C3—C2 | 97.93 (16) | N1'—C3'—C5' | 109.63 (16) |
C6—C3—C2 | 112.48 (18) | C2'—C3'—C5' | 112.18 (18) |
C5—C3—C2 | 111.95 (19) | C6'—C3'—C5' | 110.12 (17) |
C1—C4—H4A | 109.5 | C1'—C4'—H4D | 109.5 |
C1—C4—H4B | 109.5 | C1'—C4'—H4E | 109.5 |
H4A—C4—H4B | 109.5 | H4D—C4'—H4E | 109.5 |
C1—C4—H4C | 109.5 | C1'—C4'—H4F | 109.5 |
H4A—C4—H4C | 109.5 | H4D—C4'—H4F | 109.5 |
H4B—C4—H4C | 109.5 | H4E—C4'—H4F | 109.5 |
C3—C5—H5A | 109.5 | C3'—C6'—H6D | 109.5 |
C3—C5—H5B | 109.5 | C3'—C6'—H6E | 109.5 |
H5A—C5—H5B | 109.5 | H6D—C6'—H6E | 109.5 |
C3—C5—H5C | 109.5 | C3'—C6'—H6F | 109.5 |
H5A—C5—H5C | 109.5 | H6D—C6'—H6F | 109.5 |
H5B—C5—H5C | 109.5 | H6E—C6'—H6F | 109.5 |
C3—C6—H6A | 109.5 | C3'—C5'—H5D | 109.5 |
C3—C6—H6B | 109.5 | C3'—C5'—H5E | 109.5 |
H6A—C6—H6B | 109.5 | H5D—C5'—H5E | 109.5 |
C3—C6—H6C | 109.5 | C3'—C5'—H5F | 109.5 |
H6A—C6—H6C | 109.5 | H5D—C5'—H5F | 109.5 |
H6B—C6—H6C | 109.5 | H5E—C5'—H5F | 109.5 |
C12—C7—C8 | 119.3 (2) | C12'—C7'—C8' | 119.0 (2) |
C12—C7—N1 | 124.8 (2) | C12'—C7'—N1' | 124.52 (18) |
C8—C7—N1 | 115.9 (2) | C8'—C7'—N1' | 116.51 (19) |
C9—C8—C7 | 120.5 (3) | C9'—C8'—C7' | 120.4 (2) |
C9—C8—H8A | 119.8 | C9'—C8'—H8B | 119.8 |
C7—C8—H8A | 119.8 | C7'—C8'—H8B | 119.8 |
C10—C9—C8 | 121.7 (3) | C10'—C9'—C8' | 121.7 (2) |
C10—C9—H9A | 119.1 | C10'—C9'—H9B | 119.2 |
C8—C9—H9A | 119.1 | C8'—C9'—H9B | 119.2 |
C9—C10—C11 | 117.6 (3) | C9'—C10'—C11' | 118.3 (2) |
C9—C10—C21 | 121.4 (3) | C9'—C10'—C21' | 121.7 (3) |
C11—C10—C21 | 121.0 (3) | C11'—C10'—C21' | 119.9 (3) |
C12—C11—C10 | 121.8 (3) | C10'—C11'—C12' | 120.7 (2) |
C12—C11—H11A | 119.1 | C10'—C11'—H11B | 119.6 |
C10—C11—H11A | 119.1 | C12'—C11'—H11B | 119.6 |
C7—C12—C11 | 119.0 (2) | C7'—C12'—C11' | 119.8 (2) |
C7—C12—H12A | 120.5 | C7'—C12'—H12B | 120.1 |
C11—C12—H12A | 120.5 | C11'—C12'—H12B | 120.1 |
O2—C13—N2 | 124.7 (2) | O2'—C13'—N2' | 124.77 (19) |
O2—C13—C14 | 127.3 (2) | O2'—C13'—C14' | 126.7 (2) |
N2—C13—C14 | 107.96 (19) | N2'—C13'—C14' | 108.56 (18) |
C15—C14—C13 | 103.87 (17) | C15'—C14'—C13' | 103.20 (17) |
C15—C14—H14A | 111.0 | C15'—C14'—H14C | 111.1 |
C13—C14—H14A | 111.0 | C13'—C14'—H14C | 111.1 |
C15—C14—H14B | 111.0 | C15'—C14'—H14D | 111.1 |
C13—C14—H14B | 111.0 | C13'—C14'—H14D | 111.1 |
H14A—C14—H14B | 109.0 | H14C—C14'—H14D | 109.1 |
C16—C15—C20 | 120.7 (2) | C16'—C15'—C20' | 120.59 (19) |
C16—C15—C14 | 130.51 (19) | C16'—C15'—C14' | 130.32 (19) |
C20—C15—C14 | 108.79 (18) | C20'—C15'—C14' | 109.07 (17) |
C15—C16—C17 | 120.5 (2) | C15'—C16'—C17' | 120.0 (2) |
C15—C16—H16A | 119.7 | C15'—C16'—H16B | 120.0 |
C17—C16—H16A | 119.7 | C17'—C16'—H16B | 120.0 |
C18—C17—C16 | 117.7 (2) | C18'—C17'—C16' | 117.96 (19) |
C18—C17—C22 | 121.6 (2) | C18'—C17'—C22' | 121.4 (2) |
C16—C17—C22 | 120.7 (2) | C16'—C17'—C22' | 120.7 (2) |
C17—C18—C19 | 123.4 (2) | C17'—C18'—C19' | 123.2 (2) |
C17—C18—H18A | 118.3 | C17'—C18'—H18B | 118.4 |
C19—C18—H18A | 118.3 | C19'—C18'—H18B | 118.4 |
C20—C19—C18 | 117.5 (2) | C20'—C19'—C18' | 117.5 (2) |
C20—C19—H19A | 121.2 | C20'—C19'—H19B | 121.2 |
C18—C19—H19A | 121.2 | C18'—C19'—H19B | 121.2 |
C19—C20—C15 | 120.1 (2) | C19'—C20'—C15' | 120.61 (19) |
C19—C20—N2 | 130.8 (2) | C19'—C20'—N2' | 130.55 (19) |
C15—C20—N2 | 109.08 (18) | C15'—C20'—N2' | 108.84 (17) |
C10—C21—H21A | 109.5 | C10'—C21'—H21D | 109.5 |
C10—C21—H21B | 109.5 | C10'—C21'—H21E | 109.5 |
H21A—C21—H21B | 109.5 | H21D—C21'—H21E | 109.5 |
C10—C21—H21C | 109.5 | C10'—C21'—H21F | 109.5 |
H21A—C21—H21C | 109.5 | H21D—C21'—H21F | 109.5 |
H21B—C21—H21C | 109.5 | H21E—C21'—H21F | 109.5 |
C17—C22—H22A | 109.5 | C17'—C22'—H22D | 109.5 |
C17—C22—H22B | 109.5 | C17'—C22'—H22E | 109.5 |
H22A—C22—H22B | 109.5 | H22D—C22'—H22E | 109.5 |
C17—C22—H22C | 109.5 | C17'—C22'—H22F | 109.5 |
H22A—C22—H22C | 109.5 | H22D—C22'—H22F | 109.5 |
H22B—C22—H22C | 109.5 | H22E—C22'—H22F | 109.5 |
C1—O1—N1—C7 | −172.94 (16) | C1'—O1'—N1'—C7' | −170.79 (15) |
C1—O1—N1—C3 | −49.92 (18) | C1'—O1'—N1'—C3' | −47.98 (17) |
N1—O1—C1—N2 | −91.77 (17) | N1'—O1'—C1'—N2' | −94.07 (16) |
N1—O1—C1—C4 | 151.06 (16) | N1'—O1'—C1'—C4' | 148.85 (15) |
N1—O1—C1—C2 | 27.59 (19) | N1'—O1'—C1'—C2' | 25.71 (18) |
C13—N2—C1—O1 | 170.00 (15) | C13'—N2'—C1'—O1' | 166.29 (15) |
C20—N2—C1—O1 | −25.5 (2) | C20'—N2'—C1'—O1' | −35.8 (2) |
C13—N2—C1—C4 | −73.8 (2) | C13'—N2'—C1'—C4' | −77.7 (2) |
C20—N2—C1—C4 | 90.7 (2) | C20'—N2'—C1'—C4' | 80.2 (2) |
C13—N2—C1—C2 | 54.7 (2) | C13'—N2'—C1'—C2' | 50.8 (2) |
C20—N2—C1—C2 | −140.79 (18) | C20'—N2'—C1'—C2' | −151.31 (16) |
O1—C1—C2—C3 | 4.1 (2) | O1'—C1'—C2'—C3' | 5.2 (2) |
N2—C1—C2—C3 | 122.16 (18) | N2'—C1'—C2'—C3' | 123.58 (17) |
C4—C1—C2—C3 | −113.4 (2) | C4'—C1'—C2'—C3' | −111.98 (19) |
C7—N1—C3—C6 | 47.6 (2) | C7'—N1'—C3'—C2' | 164.90 (16) |
O1—N1—C3—C6 | −69.31 (19) | O1'—N1'—C3'—C2' | 48.46 (16) |
C7—N1—C3—C5 | −76.8 (2) | C7'—N1'—C3'—C6' | 46.0 (2) |
O1—N1—C3—C5 | 166.30 (16) | O1'—N1'—C3'—C6' | −70.48 (18) |
C7—N1—C3—C2 | 166.44 (17) | C7'—N1'—C3'—C5' | −77.8 (2) |
O1—N1—C3—C2 | 49.53 (18) | O1'—N1'—C3'—C5' | 165.76 (15) |
C1—C2—C3—N1 | −32.8 (2) | C1'—C2'—C3'—N1' | −32.80 (19) |
C1—C2—C3—C6 | 87.0 (2) | C1'—C2'—C3'—C6' | 87.2 (2) |
C1—C2—C3—C5 | −147.72 (18) | C1'—C2'—C3'—C5' | −148.13 (17) |
O1—N1—C7—C12 | 22.3 (3) | O1'—N1'—C7'—C12' | 20.1 (3) |
C3—N1—C7—C12 | −90.5 (3) | C3'—N1'—C7'—C12' | −92.8 (2) |
O1—N1—C7—C8 | −158.02 (18) | O1'—N1'—C7'—C8' | −158.76 (17) |
C3—N1—C7—C8 | 89.2 (2) | C3'—N1'—C7'—C8' | 88.4 (2) |
C12—C7—C8—C9 | 2.9 (4) | C12'—C7'—C8'—C9' | 2.4 (3) |
N1—C7—C8—C9 | −176.8 (2) | N1'—C7'—C8'—C9' | −178.6 (2) |
C7—C8—C9—C10 | −1.2 (4) | C7'—C8'—C9'—C10' | −3.0 (4) |
C8—C9—C10—C11 | −1.5 (4) | C8'—C9'—C10'—C11' | 1.7 (4) |
C8—C9—C10—C21 | 178.4 (2) | C8'—C9'—C10'—C21' | −179.1 (2) |
C9—C10—C11—C12 | 2.7 (4) | C9'—C10'—C11'—C12' | 0.1 (4) |
C21—C10—C11—C12 | −177.3 (2) | C21'—C10'—C11'—C12' | −179.1 (2) |
C8—C7—C12—C11 | −1.7 (3) | C8'—C7'—C12'—C11' | −0.6 (3) |
N1—C7—C12—C11 | 178.0 (2) | N1'—C7'—C12'—C11' | −179.4 (2) |
C10—C11—C12—C7 | −1.1 (4) | C10'—C11'—C12'—C7' | −0.7 (4) |
C20—N2—C13—O2 | −173.54 (18) | C20'—N2'—C13'—O2' | −170.16 (17) |
C1—N2—C13—O2 | −6.4 (3) | C1'—N2'—C13'—O2' | −9.0 (3) |
C20—N2—C13—C14 | 5.5 (2) | C20'—N2'—C13'—C14' | 9.24 (19) |
C1—N2—C13—C14 | 172.68 (15) | C1'—N2'—C13'—C14' | 170.36 (15) |
O2—C13—C14—C15 | 176.01 (18) | O2'—C13'—C14'—C15' | 173.00 (18) |
N2—C13—C14—C15 | −3.04 (19) | N2'—C13'—C14'—C15' | −6.39 (19) |
C13—C14—C15—C16 | 179.57 (18) | C13'—C14'—C15'—C16' | −177.19 (18) |
C13—C14—C15—C20 | −0.56 (19) | C13'—C14'—C15'—C20' | 1.22 (19) |
C20—C15—C16—C17 | −2.6 (3) | C20'—C15'—C16'—C17' | −2.7 (3) |
C14—C15—C16—C17 | 177.24 (18) | C14'—C15'—C16'—C17' | 175.56 (17) |
C15—C16—C17—C18 | 0.5 (3) | C15'—C16'—C17'—C18' | 0.3 (3) |
C15—C16—C17—C22 | −178.60 (18) | C15'—C16'—C17'—C22' | −178.22 (17) |
C16—C17—C18—C19 | 1.8 (3) | C16'—C17'—C18'—C19' | 2.1 (3) |
C22—C17—C18—C19 | −179.1 (2) | C22'—C17'—C18'—C19' | −179.36 (18) |
C17—C18—C19—C20 | −1.9 (3) | C17'—C18'—C19'—C20' | −2.0 (3) |
C18—C19—C20—C15 | −0.3 (3) | C18'—C19'—C20'—C15' | −0.4 (3) |
C18—C19—C20—N2 | 178.12 (18) | C18'—C19'—C20'—N2' | 179.55 (17) |
C16—C15—C20—C19 | 2.5 (3) | C16'—C15'—C20'—C19' | 2.7 (3) |
C14—C15—C20—C19 | −177.39 (17) | C14'—C15'—C20'—C19' | −175.86 (16) |
C16—C15—C20—N2 | −176.23 (15) | C16'—C15'—C20'—N2' | −177.21 (15) |
C14—C15—C20—N2 | 3.9 (2) | C14'—C15'—C20'—N2' | 4.19 (19) |
C13—N2—C20—C19 | 175.44 (19) | C13'—N2'—C20'—C19' | 171.53 (18) |
C1—N2—C20—C19 | 9.7 (3) | C1'—N2'—C20'—C19' | 11.4 (3) |
C13—N2—C20—C15 | −6.0 (2) | C13'—N2'—C20'—C15' | −8.52 (19) |
C1—N2—C20—C15 | −171.75 (17) | C1'—N2'—C20'—C15' | −168.62 (15) |