Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056170/cv2168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056170/cv2168Isup2.hkl |
CCDC reference: 636228
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.119
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 30 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: enCIFer (Allen et al., 2004).
C38H33NO | Z = 2 |
Mr = 519.65 | F(000) = 552 |
Triclinic, P1 | Dx = 1.202 Mg m−3 |
Hall symbol: -P 1 | Melting point: 428 K |
a = 10.1507 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1701 (3) Å | Cell parameters from 6037 reflections |
c = 14.3299 (3) Å | θ = 1–27.5° |
α = 91.3388 (16)° | µ = 0.07 mm−1 |
β = 100.0688 (17)° | T = 150 K |
γ = 115.4451 (11)° | Prism, colourless |
V = 1435.69 (6) Å3 | 0.4 × 0.25 × 0.18 mm |
Nonius KappaCCD area-detector diffractometer | 4982 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
Detector resolution: 9.091 pixels mm-1 | h = −13→13 |
φ and ω scans to fill the Ewald sphere | k = −14→14 |
23210 measured reflections | l = −18→18 |
6577 independent reflections |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4091P] where P = (Fo2 + 2Fc2)/3 |
6577 reflections | (Δ/σ)max < 0.001 |
367 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 7.69 (m, 2H), 7.29 (m, 2H), 7.13–7.00 (m, 20H), 3.34 (s, 2H), 1.97 (s, 6H); IR (TlBr disc, ν, cm-1): 3439 (br versus), 3050 (m), 2925 (s), 2847 (m), 2777 (w), 1598 (s), 1574 (m), 1489 (s), 1442 (s), 1368 (w), 1313 (w), 1251 (s), 1174 (s), 1134 (w), 1103 (m), 1072 (m), 1029 (m), 1010 (m), 924 (m), 873 (w), 811 (m), 784 (s), 745 (versus), 698 (versus), 667 (m), 620 (w), 573 (m), 554 (s), 457 (m); Raman (quartz capillary, cm-1): 3061 (m), 3051 (m), 2997 (w), 2960 (m), 2821 (w), 2778 (w), 1632 (m), 1607 (versus), 1598 (s), 1581 (s), 1566 (m), 1497 (m), 1441 (w), 1336 (m), 1326 (m), 1307 (m), 1177 (w), 1156 (w), 1003 (s), 980 (s), 924 (m), 404 (m), 152 (m), 125 (s), 108 (s), 85 (s). Elemental analysis, calculated for C38H33NO: C 87.83, H 6.40, N 2.70%; found: C 88.02, H 6.44, N 2.66%. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.43538 (14) | 0.46360 (12) | 0.18545 (8) | 0.0215 (3) | |
C2 | 0.58389 (14) | 0.46480 (12) | 0.23292 (9) | 0.0213 (3) | |
C3 | 0.65320 (14) | 0.56303 (12) | 0.30562 (9) | 0.0211 (3) | |
C4 | 0.56418 (14) | 0.63871 (12) | 0.31017 (9) | 0.0213 (3) | |
C5 | 0.44190 (14) | 0.58764 (12) | 0.23854 (9) | 0.0220 (3) | |
C11 | 0.30835 (14) | 0.33460 (12) | 0.20779 (9) | 0.0216 (3) | |
C12 | 0.19779 (14) | 0.23205 (13) | 0.14002 (9) | 0.0247 (3) | |
C13 | 0.09481 (16) | 0.11987 (14) | 0.17302 (10) | 0.0338 (3) | |
H13 | 0.0221 | 0.0512 | 0.1286 | 0.041* | |
C14 | 0.09672 (17) | 0.10696 (15) | 0.26840 (11) | 0.0369 (4) | |
H14 | 0.0266 | 0.0310 | 0.2878 | 0.044* | |
C15 | 0.20399 (16) | 0.20822 (14) | 0.33494 (10) | 0.0303 (3) | |
H15 | 0.2065 | 0.2016 | 0.3997 | 0.036* | |
C16 | 0.30750 (15) | 0.31942 (13) | 0.30443 (9) | 0.0255 (3) | |
H16 | 0.3796 | 0.3870 | 0.3499 | 0.031* | |
C17 | 0.17914 (15) | 0.23150 (14) | 0.03303 (9) | 0.0270 (3) | |
H17A | 0.0891 | 0.1535 | 0.0030 | 0.032* | |
H17B | 0.1667 | 0.3098 | 0.0150 | 0.032* | |
C18 | 0.32977 (18) | 0.11478 (15) | 0.02145 (11) | 0.0359 (3) | |
H18A | 0.2396 | 0.0349 | −0.0015 | 0.054* | |
H18B | 0.3580 | 0.1197 | 0.0895 | 0.054* | |
H18C | 0.4078 | 0.1136 | −0.0074 | 0.054* | |
C19 | 0.28084 (18) | 0.23510 (16) | −0.10642 (10) | 0.0401 (4) | |
H19A | 0.3655 | 0.2381 | −0.1293 | 0.060* | |
H19B | 0.2677 | 0.3132 | −0.1210 | 0.060* | |
H19C | 0.1933 | 0.1569 | −0.1368 | 0.060* | |
C21 | 0.63257 (14) | 0.36414 (13) | 0.20549 (9) | 0.0247 (3) | |
C22 | 0.67269 (16) | 0.35842 (15) | 0.11780 (10) | 0.0327 (3) | |
H22 | 0.6645 | 0.4159 | 0.0737 | 0.039* | |
C23 | 0.72488 (19) | 0.26679 (18) | 0.09629 (13) | 0.0464 (4) | |
H23 | 0.7525 | 0.2639 | 0.0380 | 0.056* | |
C24 | 0.7360 (2) | 0.18026 (19) | 0.16077 (14) | 0.0545 (5) | |
H24 | 0.7718 | 0.1197 | 0.1462 | 0.065* | |
C25 | 0.6939 (2) | 0.18334 (18) | 0.24712 (13) | 0.0524 (5) | |
H25 | 0.7000 | 0.1241 | 0.2903 | 0.063* | |
C26 | 0.64259 (18) | 0.27481 (15) | 0.26905 (11) | 0.0365 (4) | |
H26 | 0.6144 | 0.2766 | 0.3272 | 0.044* | |
C31 | 0.79909 (14) | 0.59737 (12) | 0.36954 (9) | 0.0225 (3) | |
C32 | 0.81595 (16) | 0.60790 (13) | 0.46826 (9) | 0.0279 (3) | |
H32 | 0.7337 | 0.5909 | 0.4954 | 0.034* | |
C33 | 0.95460 (17) | 0.64359 (14) | 0.52677 (10) | 0.0344 (3) | |
H33 | 0.9648 | 0.6502 | 0.5927 | 0.041* | |
C34 | 1.07694 (17) | 0.66909 (15) | 0.48706 (11) | 0.0363 (4) | |
H34 | 1.1697 | 0.6932 | 0.5263 | 0.044* | |
C35 | 1.06244 (16) | 0.65899 (15) | 0.38939 (11) | 0.0361 (3) | |
H35 | 1.1452 | 0.6764 | 0.3628 | 0.043* | |
C36 | 0.92423 (15) | 0.62287 (14) | 0.33098 (10) | 0.0300 (3) | |
H36 | 0.9148 | 0.6155 | 0.2651 | 0.036* | |
C41 | 0.60974 (14) | 0.75458 (12) | 0.38148 (9) | 0.0221 (3) | |
C42 | 0.74949 (15) | 0.86359 (13) | 0.39185 (10) | 0.0273 (3) | |
H42 | 0.8164 | 0.8614 | 0.3558 | 0.033* | |
C43 | 0.78964 (17) | 0.97496 (14) | 0.45527 (11) | 0.0332 (3) | |
H43 | 0.8822 | 1.0477 | 0.4607 | 0.040* | |
C44 | 0.69194 (18) | 0.97781 (15) | 0.51037 (11) | 0.0365 (4) | |
H44 | 0.7185 | 1.0527 | 0.5527 | 0.044* | |
C45 | 0.55438 (17) | 0.86916 (15) | 0.50260 (10) | 0.0336 (3) | |
H45 | 0.4893 | 0.8707 | 0.5404 | 0.040* | |
C46 | 0.51348 (15) | 0.75822 (14) | 0.43874 (9) | 0.0267 (3) | |
H46 | 0.4210 | 0.6855 | 0.4340 | 0.032* | |
C51 | 0.33635 (14) | 0.64322 (13) | 0.20588 (9) | 0.0241 (3) | |
C52 | 0.38298 (16) | 0.78141 (14) | 0.21629 (10) | 0.0304 (3) | |
H52 | 0.4817 | 0.8378 | 0.2439 | 0.037* | |
C53 | 0.28544 (18) | 0.83556 (16) | 0.18632 (11) | 0.0363 (3) | |
H53 | 0.3182 | 0.9274 | 0.1955 | 0.044* | |
C54 | 0.13909 (18) | 0.75359 (16) | 0.14273 (11) | 0.0369 (4) | |
H54 | 0.0731 | 0.7898 | 0.1228 | 0.044* | |
C55 | 0.09216 (17) | 0.61756 (16) | 0.12915 (11) | 0.0350 (3) | |
H55 | −0.0055 | 0.5622 | 0.0987 | 0.042* | |
C56 | 0.18886 (15) | 0.56253 (15) | 0.16035 (10) | 0.0300 (3) | |
H56 | 0.1551 | 0.4706 | 0.1509 | 0.036* | |
N1 | 0.30531 (13) | 0.23068 (11) | −0.00318 (8) | 0.0279 (3) | |
O1 | 0.42618 (10) | 0.48103 (9) | 0.08751 (6) | 0.0247 (2) | |
H1 | 0.410 (2) | 0.398 (2) | 0.0569 (14) | 0.063 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0218 (6) | 0.0211 (6) | 0.0182 (6) | 0.0068 (5) | 0.0027 (5) | 0.0013 (5) |
C2 | 0.0202 (6) | 0.0212 (6) | 0.0208 (6) | 0.0069 (5) | 0.0058 (5) | 0.0027 (5) |
C3 | 0.0209 (6) | 0.0208 (6) | 0.0202 (6) | 0.0073 (5) | 0.0056 (5) | 0.0029 (5) |
C4 | 0.0219 (6) | 0.0183 (6) | 0.0213 (6) | 0.0060 (5) | 0.0061 (5) | 0.0021 (5) |
C5 | 0.0212 (6) | 0.0198 (6) | 0.0230 (6) | 0.0064 (5) | 0.0066 (5) | 0.0036 (5) |
C11 | 0.0204 (6) | 0.0200 (6) | 0.0234 (6) | 0.0080 (5) | 0.0046 (5) | 0.0026 (5) |
C12 | 0.0220 (7) | 0.0239 (6) | 0.0245 (6) | 0.0069 (5) | 0.0046 (5) | 0.0014 (5) |
C13 | 0.0283 (7) | 0.0266 (7) | 0.0331 (8) | −0.0003 (6) | 0.0073 (6) | −0.0017 (6) |
C14 | 0.0361 (8) | 0.0276 (7) | 0.0368 (8) | 0.0012 (6) | 0.0161 (7) | 0.0054 (6) |
C15 | 0.0348 (8) | 0.0311 (7) | 0.0262 (7) | 0.0132 (6) | 0.0122 (6) | 0.0060 (6) |
C16 | 0.0255 (7) | 0.0249 (7) | 0.0238 (6) | 0.0090 (6) | 0.0048 (5) | 0.0013 (5) |
C17 | 0.0232 (7) | 0.0244 (7) | 0.0242 (7) | 0.0039 (6) | −0.0001 (5) | −0.0006 (5) |
C18 | 0.0375 (8) | 0.0282 (7) | 0.0382 (8) | 0.0108 (7) | 0.0090 (7) | −0.0015 (6) |
C19 | 0.0421 (9) | 0.0341 (8) | 0.0237 (7) | −0.0020 (7) | 0.0073 (6) | −0.0012 (6) |
C21 | 0.0205 (6) | 0.0232 (6) | 0.0253 (7) | 0.0067 (5) | 0.0007 (5) | −0.0046 (5) |
C22 | 0.0296 (8) | 0.0331 (8) | 0.0312 (7) | 0.0099 (6) | 0.0074 (6) | −0.0041 (6) |
C23 | 0.0414 (9) | 0.0525 (10) | 0.0467 (10) | 0.0227 (8) | 0.0100 (7) | −0.0165 (8) |
C24 | 0.0570 (12) | 0.0545 (11) | 0.0597 (12) | 0.0394 (10) | −0.0051 (9) | −0.0214 (9) |
C25 | 0.0718 (13) | 0.0457 (10) | 0.0475 (10) | 0.0411 (10) | −0.0076 (9) | −0.0061 (8) |
C26 | 0.0465 (9) | 0.0341 (8) | 0.0301 (8) | 0.0220 (7) | 0.0002 (7) | −0.0022 (6) |
C31 | 0.0232 (7) | 0.0182 (6) | 0.0242 (6) | 0.0088 (5) | 0.0014 (5) | −0.0010 (5) |
C32 | 0.0309 (7) | 0.0261 (7) | 0.0255 (7) | 0.0129 (6) | 0.0025 (5) | −0.0014 (5) |
C33 | 0.0434 (9) | 0.0295 (7) | 0.0268 (7) | 0.0181 (7) | −0.0062 (6) | −0.0036 (6) |
C34 | 0.0298 (8) | 0.0284 (7) | 0.0429 (9) | 0.0130 (6) | −0.0114 (6) | −0.0059 (6) |
C35 | 0.0234 (7) | 0.0339 (8) | 0.0464 (9) | 0.0104 (6) | 0.0026 (6) | −0.0018 (7) |
C36 | 0.0255 (7) | 0.0319 (7) | 0.0289 (7) | 0.0102 (6) | 0.0036 (6) | −0.0003 (6) |
C41 | 0.0234 (7) | 0.0204 (6) | 0.0223 (6) | 0.0103 (5) | 0.0021 (5) | 0.0019 (5) |
C42 | 0.0259 (7) | 0.0234 (7) | 0.0306 (7) | 0.0091 (6) | 0.0057 (5) | 0.0030 (5) |
C43 | 0.0332 (8) | 0.0198 (7) | 0.0384 (8) | 0.0074 (6) | −0.0009 (6) | 0.0000 (6) |
C44 | 0.0488 (9) | 0.0261 (7) | 0.0342 (8) | 0.0195 (7) | 0.0002 (7) | −0.0055 (6) |
C45 | 0.0426 (9) | 0.0349 (8) | 0.0308 (7) | 0.0235 (7) | 0.0096 (6) | 0.0006 (6) |
C46 | 0.0267 (7) | 0.0248 (7) | 0.0286 (7) | 0.0115 (6) | 0.0054 (5) | 0.0024 (5) |
C51 | 0.0245 (7) | 0.0272 (7) | 0.0213 (6) | 0.0115 (6) | 0.0057 (5) | 0.0029 (5) |
C52 | 0.0294 (7) | 0.0274 (7) | 0.0317 (7) | 0.0114 (6) | 0.0019 (6) | 0.0045 (6) |
C53 | 0.0425 (9) | 0.0320 (8) | 0.0380 (8) | 0.0212 (7) | 0.0032 (7) | 0.0069 (6) |
C54 | 0.0389 (9) | 0.0478 (9) | 0.0345 (8) | 0.0290 (8) | 0.0060 (7) | 0.0092 (7) |
C55 | 0.0249 (7) | 0.0453 (9) | 0.0345 (8) | 0.0169 (7) | 0.0022 (6) | 0.0015 (7) |
C56 | 0.0251 (7) | 0.0307 (7) | 0.0322 (7) | 0.0110 (6) | 0.0046 (6) | −0.0002 (6) |
N1 | 0.0297 (6) | 0.0249 (6) | 0.0213 (5) | 0.0050 (5) | 0.0051 (5) | −0.0004 (4) |
O1 | 0.0280 (5) | 0.0217 (5) | 0.0187 (4) | 0.0064 (4) | 0.0033 (4) | 0.0022 (4) |
C1—O1 | 1.4138 (15) | C24—C25 | 1.382 (3) |
C1—C5 | 1.5353 (17) | C24—H24 | 0.9300 |
C1—C2 | 1.5360 (18) | C25—C26 | 1.383 (2) |
C1—C11 | 1.5527 (17) | C25—H25 | 0.9300 |
C2—C3 | 1.3458 (17) | C26—H26 | 0.9300 |
C2—C21 | 1.4790 (18) | C31—C32 | 1.3910 (18) |
C3—C31 | 1.4834 (18) | C31—C36 | 1.3935 (19) |
C3—C4 | 1.4866 (18) | C32—C33 | 1.390 (2) |
C4—C5 | 1.3559 (18) | C32—H32 | 0.9300 |
C4—C41 | 1.4805 (17) | C33—C34 | 1.378 (2) |
C5—C51 | 1.4704 (19) | C33—H33 | 0.9300 |
C11—C16 | 1.4003 (18) | C34—C35 | 1.378 (2) |
C11—C12 | 1.4060 (17) | C34—H34 | 0.9300 |
C12—C13 | 1.4006 (19) | C35—C36 | 1.385 (2) |
C12—C17 | 1.5111 (18) | C35—H35 | 0.9300 |
C13—C14 | 1.375 (2) | C36—H36 | 0.9300 |
C13—H13 | 0.9300 | C41—C46 | 1.3937 (18) |
C14—C15 | 1.379 (2) | C41—C42 | 1.3967 (18) |
C14—H14 | 0.9300 | C42—C43 | 1.3861 (19) |
C15—C16 | 1.3793 (19) | C42—H42 | 0.9300 |
C15—H15 | 0.9300 | C43—C44 | 1.381 (2) |
C16—H16 | 0.9300 | C43—H43 | 0.9300 |
C17—N1 | 1.4669 (18) | C44—C45 | 1.385 (2) |
C17—H17A | 0.9700 | C44—H44 | 0.9300 |
C17—H17B | 0.9700 | C45—C46 | 1.3847 (19) |
C18—N1 | 1.4592 (19) | C45—H45 | 0.9300 |
C18—H18A | 0.9600 | C46—H46 | 0.9300 |
C18—H18B | 0.9600 | C51—C56 | 1.3968 (19) |
C18—H18C | 0.9600 | C51—C52 | 1.4021 (19) |
C19—N1 | 1.4623 (17) | C52—C53 | 1.381 (2) |
C19—H19A | 0.9600 | C52—H52 | 0.9300 |
C19—H19B | 0.9600 | C53—C54 | 1.384 (2) |
C19—H19C | 0.9600 | C53—H53 | 0.9300 |
C21—C26 | 1.390 (2) | C54—C55 | 1.380 (2) |
C21—C22 | 1.3952 (19) | C54—H54 | 0.9300 |
C22—C23 | 1.390 (2) | C55—C56 | 1.385 (2) |
C22—H22 | 0.9300 | C55—H55 | 0.9300 |
C23—C24 | 1.378 (3) | C56—H56 | 0.9300 |
C23—H23 | 0.9300 | O1—H1 | 0.95 (2) |
O1—C1—C5 | 108.35 (10) | C25—C24—H24 | 120.0 |
O1—C1—C2 | 112.76 (10) | C24—C25—C26 | 119.73 (17) |
C5—C1—C2 | 102.06 (10) | C24—C25—H25 | 120.1 |
O1—C1—C11 | 114.75 (10) | C26—C25—H25 | 120.1 |
C5—C1—C11 | 110.80 (10) | C25—C26—C21 | 121.03 (15) |
C2—C1—C11 | 107.39 (10) | C25—C26—H26 | 119.5 |
C3—C2—C21 | 126.81 (12) | C21—C26—H26 | 119.5 |
C3—C2—C1 | 109.60 (11) | C32—C31—C36 | 118.38 (12) |
C21—C2—C1 | 123.40 (10) | C32—C31—C3 | 121.64 (12) |
C2—C3—C31 | 126.51 (12) | C36—C31—C3 | 119.96 (11) |
C2—C3—C4 | 109.40 (11) | C33—C32—C31 | 120.61 (14) |
C31—C3—C4 | 124.03 (11) | C33—C32—H32 | 119.7 |
C5—C4—C41 | 127.01 (12) | C31—C32—H32 | 119.7 |
C5—C4—C3 | 109.56 (11) | C34—C33—C32 | 119.98 (14) |
C41—C4—C3 | 123.40 (11) | C34—C33—H33 | 120.0 |
C4—C5—C51 | 128.44 (12) | C32—C33—H33 | 120.0 |
C4—C5—C1 | 109.00 (11) | C33—C34—C35 | 120.26 (13) |
C51—C5—C1 | 122.27 (11) | C33—C34—H34 | 119.9 |
C16—C11—C12 | 117.97 (12) | C35—C34—H34 | 119.9 |
C16—C11—C1 | 116.21 (11) | C34—C35—C36 | 119.83 (14) |
C12—C11—C1 | 125.81 (11) | C34—C35—H35 | 120.1 |
C13—C12—C11 | 118.19 (12) | C36—C35—H35 | 120.1 |
C13—C12—C17 | 116.18 (12) | C35—C36—C31 | 120.92 (13) |
C11—C12—C17 | 125.64 (12) | C35—C36—H36 | 119.5 |
C14—C13—C12 | 122.76 (13) | C31—C36—H36 | 119.5 |
C14—C13—H13 | 118.6 | C46—C41—C42 | 118.54 (12) |
C12—C13—H13 | 118.6 | C46—C41—C4 | 120.81 (12) |
C13—C14—C15 | 119.12 (13) | C42—C41—C4 | 120.65 (12) |
C13—C14—H14 | 120.4 | C43—C42—C41 | 120.76 (13) |
C15—C14—H14 | 120.4 | C43—C42—H42 | 119.6 |
C16—C15—C14 | 119.35 (13) | C41—C42—H42 | 119.6 |
C16—C15—H15 | 120.3 | C44—C43—C42 | 119.93 (14) |
C14—C15—H15 | 120.3 | C44—C43—H43 | 120.0 |
C15—C16—C11 | 122.61 (12) | C42—C43—H43 | 120.0 |
C15—C16—H16 | 118.7 | C43—C44—C45 | 119.99 (13) |
C11—C16—H16 | 118.7 | C43—C44—H44 | 120.0 |
N1—C17—C12 | 113.43 (11) | C45—C44—H44 | 120.0 |
N1—C17—H17A | 108.9 | C46—C45—C44 | 120.21 (14) |
C12—C17—H17A | 108.9 | C46—C45—H45 | 119.9 |
N1—C17—H17B | 108.9 | C44—C45—H45 | 119.9 |
C12—C17—H17B | 108.9 | C45—C46—C41 | 120.54 (13) |
H17A—C17—H17B | 107.7 | C45—C46—H46 | 119.7 |
N1—C18—H18A | 109.5 | C41—C46—H46 | 119.7 |
N1—C18—H18B | 109.5 | C56—C51—C52 | 117.40 (13) |
H18A—C18—H18B | 109.5 | C56—C51—C5 | 122.03 (12) |
N1—C18—H18C | 109.5 | C52—C51—C5 | 120.52 (12) |
H18A—C18—H18C | 109.5 | C53—C52—C51 | 121.40 (14) |
H18B—C18—H18C | 109.5 | C53—C52—H52 | 119.3 |
N1—C19—H19A | 109.5 | C51—C52—H52 | 119.3 |
N1—C19—H19B | 109.5 | C52—C53—C54 | 120.21 (14) |
H19A—C19—H19B | 109.5 | C52—C53—H53 | 119.9 |
N1—C19—H19C | 109.5 | C54—C53—H53 | 119.9 |
H19A—C19—H19C | 109.5 | C55—C54—C53 | 119.28 (14) |
H19B—C19—H19C | 109.5 | C55—C54—H54 | 120.4 |
C26—C21—C22 | 118.73 (13) | C53—C54—H54 | 120.4 |
C26—C21—C2 | 119.68 (12) | C54—C55—C56 | 120.77 (14) |
C22—C21—C2 | 121.57 (13) | C54—C55—H55 | 119.6 |
C23—C22—C21 | 120.02 (15) | C56—C55—H55 | 119.6 |
C23—C22—H22 | 120.0 | C55—C56—C51 | 120.89 (14) |
C21—C22—H22 | 120.0 | C55—C56—H56 | 119.6 |
C24—C23—C22 | 120.40 (16) | C51—C56—H56 | 119.6 |
C24—C23—H23 | 119.8 | C18—N1—C19 | 110.77 (12) |
C22—C23—H23 | 119.8 | C18—N1—C17 | 111.60 (11) |
C23—C24—C25 | 120.08 (16) | C19—N1—C17 | 109.89 (12) |
C23—C24—H24 | 120.0 | C1—O1—H1 | 105.0 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.95 (2) | 1.80 (2) | 2.7089 (14) | 157.6 (18) |
C1—C2 | 1.536 (2) | Cp—Ph1 | 88.38 (8) |
C2—C3 | 1.3458 (18) | Cp—Ph2 | 65.43 (8) |
C3—C4 | 1.487 (2) | Cp—Ph3 | 56.26 (7) |
C1—O1 | 1.4138 (14) | Cp—Ph4 | 54.26 (7) |
C2—C1—C5 | 102.06 (10) | Cp—Ph5 | 32.59 (7) |
O1—C1—C11 | 114.76 (10) |
Cp is the cyclopentadiene ring plane defined by atoms C1–C5. Ph1, Ph2, Ph3, Ph4 and Ph5 are the aromatic ring planes defined by atoms C11–C16, C21–C26, C31–C36, C41–C46 and C51–C56, respectively. |