The crystal structure of the title compound, C
34H
31NO
8, is stabilized by intramolecular C—H
O and N—H
O hydrogen bonds, intermolecular C—H
O hydrogen bonds, and C—H
π and π–π interactions.
Supporting information
CCDC reference: 100268
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.134
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: P3 (Siemens, 1995); cell refinement: P3; data reduction: XDISK (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1995); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
Ethyl 4-benzyloxycarbonyl-5-[2,2-bis(benzyloxycarbonyl)vinyl]-
3-methylpyrrole-2-carboxylate
top
Crystal data top
C34H31NO8 | Z = 2 |
Mr = 581.60 | F(000) = 612 |
Triclinic, P1 | Dx = 1.327 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.966 (3) Å | Cell parameters from 35 reflections |
b = 12.037 (3) Å | θ = 18–22° |
c = 14.349 (4) Å | µ = 0.10 mm−1 |
α = 72.09 (2)° | T = 130 K |
β = 83.67 (2)° | Needle, colorless |
γ = 82.02 (2)° | 0.40 × 0.20 × 0.16 mm |
V = 1455.5 (8) Å3 | |
Data collection top
Siemens R3m/V diffractometer | Rint = 0.032 |
Radiation source: fine-focus sealed tube | θmax = 26.1°, θmin = 1.5° |
Graphite monochromator | h = −10→11 |
ω scans | k = −13→14 |
5965 measured reflections | l = 0→17 |
5727 independent reflections | 2 standard reflections every 198 reflections |
3812 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4579P] where P = (Fo2 + 2Fc2)/3 |
5727 reflections | (Δ/σ)max < 0.001 |
394 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 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. The only Alert generated by CIFCHECK "Large Non-Solvent H
Ueq(max)/Ueq(min)" refers to the pyrrole nitrogen which was
refined with free isotropic variables. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.3986 (2) | 0.65391 (17) | 0.46627 (15) | 0.0241 (4) | |
H1 | 0.417 (3) | 0.689 (2) | 0.401 (2) | 0.045 (8)* | |
C2 | 0.4492 (3) | 0.6851 (2) | 0.53999 (17) | 0.0245 (5) | |
C3 | 0.3974 (3) | 0.6123 (2) | 0.62985 (17) | 0.0250 (5) | |
C4 | 0.3121 (3) | 0.5337 (2) | 0.60797 (17) | 0.0255 (5) | |
C5 | 0.3140 (3) | 0.5627 (2) | 0.50431 (17) | 0.0241 (5) | |
C21 | 0.5417 (3) | 0.7831 (2) | 0.51643 (18) | 0.0274 (5) | |
C22 | 0.6489 (3) | 0.9302 (2) | 0.3853 (2) | 0.0349 (6) | |
H22A | 0.7467 | 0.9147 | 0.4156 | 0.042* | |
H22B | 0.5882 | 0.9969 | 0.4032 | 0.042* | |
C23 | 0.6741 (4) | 0.9582 (3) | 0.2764 (2) | 0.0592 (9) | |
H23A | 0.7224 | 1.0308 | 0.2500 | 0.089* | |
H23B | 0.5769 | 0.9684 | 0.2478 | 0.089* | |
H23C | 0.7396 | 0.8936 | 0.2598 | 0.089* | |
O1 | 0.5865 (2) | 0.82078 (16) | 0.57616 (13) | 0.0394 (5) | |
O2 | 0.56877 (19) | 0.82627 (15) | 0.41928 (12) | 0.0324 (4) | |
C31 | 0.4282 (3) | 0.6200 (2) | 0.72878 (18) | 0.0341 (6) | |
H31A | 0.4989 | 0.6782 | 0.7200 | 0.051* | |
H31B | 0.4723 | 0.5431 | 0.7684 | 0.051* | |
H31C | 0.3334 | 0.6435 | 0.7622 | 0.051* | |
C41 | 0.2374 (3) | 0.4364 (2) | 0.67671 (17) | 0.0271 (5) | |
C42 | 0.2000 (4) | 0.3226 (3) | 0.84204 (19) | 0.0461 (8) | |
H42A | 0.2040 | 0.2562 | 0.8145 | 0.055* | |
H42B | 0.0930 | 0.3461 | 0.8598 | 0.055* | |
C43 | 0.2886 (3) | 0.2858 (2) | 0.93153 (18) | 0.0359 (6) | |
C44 | 0.3212 (3) | 0.3679 (3) | 0.9744 (2) | 0.0449 (7) | |
H44A | 0.2923 | 0.4491 | 0.9446 | 0.054* | |
C45 | 0.3956 (4) | 0.3324 (3) | 1.0603 (2) | 0.0512 (8) | |
H45A | 0.4164 | 0.3892 | 1.0893 | 0.061* | |
C46 | 0.4393 (4) | 0.2148 (3) | 1.1036 (2) | 0.0518 (8) | |
H46A | 0.4896 | 0.1902 | 1.1627 | 0.062* | |
C47 | 0.4098 (3) | 0.1334 (3) | 1.0608 (2) | 0.0486 (8) | |
H47A | 0.4407 | 0.0525 | 1.0903 | 0.058* | |
C48 | 0.3354 (3) | 0.1681 (3) | 0.9752 (2) | 0.0435 (7) | |
H48A | 0.3164 | 0.1109 | 0.9461 | 0.052* | |
O3 | 0.1597 (2) | 0.37514 (17) | 0.65541 (13) | 0.0499 (6) | |
O4 | 0.2645 (2) | 0.42071 (16) | 0.76981 (12) | 0.0365 (5) | |
C51 | 0.2419 (3) | 0.5062 (2) | 0.44904 (17) | 0.0239 (5) | |
H51A | 0.1971 | 0.4390 | 0.4895 | 0.029* | |
C52 | 0.2236 (3) | 0.5273 (2) | 0.35209 (17) | 0.0243 (5) | |
C53 | 0.2834 (3) | 0.6262 (2) | 0.27221 (17) | 0.0257 (5) | |
C54 | 0.2637 (3) | 0.7467 (2) | 0.10814 (17) | 0.0346 (6) | |
H54A | 0.3711 | 0.7227 | 0.0920 | 0.041* | |
H54B | 0.2561 | 0.8227 | 0.1225 | 0.041* | |
C55 | 0.1712 (3) | 0.7582 (2) | 0.02377 (17) | 0.0320 (6) | |
C56 | 0.1446 (3) | 0.6592 (3) | −0.0002 (2) | 0.0437 (7) | |
H56A | 0.1847 | 0.5834 | 0.0374 | 0.052* | |
C57 | 0.0602 (3) | 0.6703 (3) | −0.0785 (2) | 0.0521 (8) | |
H57A | 0.0424 | 0.6024 | −0.0943 | 0.063* | |
C58 | 0.0018 (3) | 0.7806 (3) | −0.1338 (2) | 0.0521 (9) | |
H58A | −0.0560 | 0.7883 | −0.1875 | 0.063* | |
C59 | 0.0270 (4) | 0.8784 (3) | −0.1112 (2) | 0.0562 (9) | |
H59A | −0.0129 | 0.9540 | −0.1494 | 0.067* | |
C510 | 0.1114 (3) | 0.8673 (3) | −0.0321 (2) | 0.0448 (7) | |
H51B | 0.1279 | 0.9356 | −0.0165 | 0.054* | |
C511 | 0.1485 (3) | 0.4407 (2) | 0.32338 (17) | 0.0275 (6) | |
C512 | 0.0169 (3) | 0.2719 (2) | 0.38549 (18) | 0.0306 (6) | |
H51C | 0.1015 | 0.2234 | 0.3613 | 0.037* | |
H51D | −0.0591 | 0.2987 | 0.3358 | 0.037* | |
C513 | −0.0535 (3) | 0.2000 (2) | 0.48200 (18) | 0.0267 (5) | |
C514 | −0.1459 (3) | 0.1165 (2) | 0.48142 (19) | 0.0319 (6) | |
H51E | −0.1659 | 0.1076 | 0.4206 | 0.038* | |
C515 | −0.2093 (3) | 0.0463 (2) | 0.5681 (2) | 0.0346 (6) | |
H51F | −0.2717 | −0.0107 | 0.5664 | 0.041* | |
C516 | −0.1819 (3) | 0.0590 (2) | 0.6570 (2) | 0.0344 (6) | |
H51G | −0.2254 | 0.0112 | 0.7167 | 0.041* | |
C517 | −0.0898 (3) | 0.1424 (2) | 0.65813 (19) | 0.0331 (6) | |
H51H | −0.0705 | 0.1515 | 0.7190 | 0.040* | |
C518 | −0.0260 (3) | 0.2123 (2) | 0.57148 (18) | 0.0289 (6) | |
H51I | 0.0369 | 0.2688 | 0.5732 | 0.035* | |
O5 | 0.39028 (19) | 0.67604 (15) | 0.27607 (12) | 0.0324 (4) | |
O6 | 0.20362 (19) | 0.65771 (15) | 0.19251 (12) | 0.0310 (4) | |
O7 | 0.1580 (2) | 0.42779 (16) | 0.24258 (13) | 0.0408 (5) | |
O8 | 0.07145 (19) | 0.37182 (14) | 0.40061 (12) | 0.0309 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0195 (10) | 0.0238 (11) | 0.0280 (11) | 0.0022 (9) | −0.0036 (9) | −0.0075 (9) |
C2 | 0.0199 (12) | 0.0226 (12) | 0.0326 (13) | 0.0036 (10) | −0.0047 (10) | −0.0123 (10) |
C3 | 0.0219 (13) | 0.0241 (13) | 0.0294 (13) | 0.0026 (10) | −0.0016 (10) | −0.0105 (10) |
C4 | 0.0240 (13) | 0.0221 (12) | 0.0300 (13) | 0.0040 (10) | −0.0042 (10) | −0.0092 (10) |
C5 | 0.0201 (12) | 0.0216 (13) | 0.0291 (13) | 0.0033 (10) | −0.0043 (10) | −0.0067 (10) |
C21 | 0.0244 (13) | 0.0258 (13) | 0.0325 (14) | 0.0023 (11) | −0.0029 (11) | −0.0110 (11) |
C22 | 0.0313 (15) | 0.0246 (14) | 0.0466 (16) | −0.0078 (12) | 0.0010 (12) | −0.0068 (12) |
C23 | 0.067 (2) | 0.057 (2) | 0.0482 (19) | −0.0239 (18) | −0.0005 (17) | −0.0022 (16) |
O1 | 0.0453 (12) | 0.0379 (11) | 0.0398 (11) | −0.0115 (9) | −0.0065 (9) | −0.0144 (9) |
O2 | 0.0317 (10) | 0.0320 (10) | 0.0350 (10) | −0.0088 (8) | 0.0004 (8) | −0.0108 (8) |
C31 | 0.0347 (15) | 0.0366 (15) | 0.0348 (14) | −0.0082 (12) | −0.0040 (12) | −0.0140 (12) |
C41 | 0.0240 (13) | 0.0276 (13) | 0.0296 (13) | 0.0047 (11) | −0.0054 (10) | −0.0107 (11) |
C42 | 0.0535 (19) | 0.0542 (19) | 0.0312 (15) | −0.0262 (16) | −0.0030 (13) | −0.0046 (13) |
C43 | 0.0382 (16) | 0.0427 (17) | 0.0262 (13) | −0.0118 (13) | 0.0054 (12) | −0.0088 (12) |
C44 | 0.0533 (19) | 0.0419 (17) | 0.0412 (16) | 0.0060 (14) | −0.0115 (14) | −0.0169 (13) |
C45 | 0.060 (2) | 0.054 (2) | 0.0446 (18) | 0.0059 (17) | −0.0137 (16) | −0.0249 (15) |
C46 | 0.057 (2) | 0.055 (2) | 0.0399 (17) | 0.0021 (17) | −0.0148 (15) | −0.0090 (15) |
C47 | 0.0491 (19) | 0.0436 (18) | 0.0462 (18) | 0.0031 (15) | −0.0031 (15) | −0.0070 (14) |
C48 | 0.0486 (18) | 0.0453 (18) | 0.0402 (16) | −0.0142 (15) | 0.0054 (14) | −0.0172 (14) |
O3 | 0.0730 (15) | 0.0491 (13) | 0.0310 (10) | −0.0313 (12) | −0.0097 (10) | −0.0042 (9) |
O4 | 0.0422 (11) | 0.0413 (11) | 0.0277 (9) | −0.0150 (9) | −0.0018 (8) | −0.0081 (8) |
C51 | 0.0194 (12) | 0.0215 (12) | 0.0284 (13) | 0.0006 (10) | −0.0010 (10) | −0.0052 (10) |
C52 | 0.0214 (12) | 0.0243 (13) | 0.0258 (12) | 0.0023 (10) | −0.0023 (10) | −0.0073 (10) |
C53 | 0.0253 (13) | 0.0255 (13) | 0.0263 (13) | 0.0031 (11) | −0.0011 (10) | −0.0107 (10) |
C54 | 0.0357 (15) | 0.0373 (16) | 0.0276 (13) | −0.0069 (13) | 0.0013 (11) | −0.0052 (11) |
C55 | 0.0297 (14) | 0.0384 (16) | 0.0230 (13) | −0.0013 (12) | 0.0021 (11) | −0.0042 (11) |
C56 | 0.0439 (18) | 0.0461 (18) | 0.0418 (16) | 0.0135 (14) | −0.0096 (14) | −0.0198 (14) |
C57 | 0.0478 (19) | 0.071 (2) | 0.0449 (18) | 0.0074 (17) | −0.0097 (15) | −0.0314 (17) |
C58 | 0.0340 (17) | 0.089 (3) | 0.0306 (15) | 0.0006 (17) | −0.0025 (13) | −0.0166 (17) |
C59 | 0.0432 (19) | 0.064 (2) | 0.0420 (18) | −0.0003 (17) | −0.0085 (15) | 0.0116 (16) |
C510 | 0.0392 (17) | 0.0443 (18) | 0.0416 (16) | −0.0061 (14) | −0.0017 (13) | 0.0012 (13) |
C511 | 0.0271 (13) | 0.0274 (14) | 0.0277 (13) | 0.0013 (11) | −0.0027 (11) | −0.0092 (11) |
C512 | 0.0317 (14) | 0.0268 (14) | 0.0379 (14) | −0.0040 (11) | −0.0035 (12) | −0.0156 (11) |
C513 | 0.0220 (13) | 0.0215 (13) | 0.0367 (14) | 0.0048 (10) | −0.0025 (11) | −0.0118 (11) |
C514 | 0.0283 (14) | 0.0277 (14) | 0.0424 (15) | −0.0009 (11) | −0.0032 (12) | −0.0154 (12) |
C515 | 0.0274 (14) | 0.0234 (14) | 0.0519 (17) | −0.0019 (11) | −0.0059 (12) | −0.0090 (12) |
C516 | 0.0299 (14) | 0.0249 (14) | 0.0416 (15) | 0.0010 (11) | 0.0019 (12) | −0.0031 (12) |
C517 | 0.0340 (15) | 0.0284 (14) | 0.0353 (14) | 0.0025 (12) | −0.0049 (12) | −0.0088 (12) |
C518 | 0.0259 (13) | 0.0214 (13) | 0.0398 (15) | −0.0011 (11) | −0.0048 (11) | −0.0095 (11) |
O5 | 0.0302 (10) | 0.0373 (11) | 0.0305 (9) | −0.0090 (8) | −0.0001 (8) | −0.0096 (8) |
O6 | 0.0290 (10) | 0.0344 (10) | 0.0253 (9) | −0.0044 (8) | −0.0008 (7) | −0.0028 (7) |
O7 | 0.0534 (13) | 0.0420 (12) | 0.0320 (10) | −0.0128 (10) | −0.0002 (9) | −0.0161 (9) |
O8 | 0.0333 (10) | 0.0299 (10) | 0.0329 (10) | −0.0101 (8) | 0.0035 (8) | −0.0136 (8) |
Geometric parameters (Å, º) top
N1—C5 | 1.360 (3) | C51—C52 | 1.359 (3) |
N1—C2 | 1.365 (3) | C51—H51A | 0.9500 |
N1—H1 | 0.91 (3) | C52—C53 | 1.490 (3) |
C2—C3 | 1.390 (3) | C52—C511 | 1.494 (3) |
C2—C21 | 1.469 (3) | C53—O5 | 1.214 (3) |
C3—C4 | 1.420 (3) | C53—O6 | 1.342 (3) |
C3—C31 | 1.508 (3) | C54—O6 | 1.456 (3) |
C4—C5 | 1.418 (3) | C54—C55 | 1.503 (3) |
C4—C41 | 1.468 (3) | C54—H54A | 0.9900 |
C5—C51 | 1.440 (3) | C54—H54B | 0.9900 |
C21—O1 | 1.211 (3) | C55—C510 | 1.381 (4) |
C21—O2 | 1.337 (3) | C55—C56 | 1.395 (4) |
C22—O2 | 1.455 (3) | C56—C57 | 1.386 (4) |
C22—C23 | 1.492 (4) | C56—H56A | 0.9500 |
C22—H22A | 0.9900 | C57—C58 | 1.384 (4) |
C22—H22B | 0.9900 | C57—H57A | 0.9500 |
C23—H23A | 0.9800 | C58—C59 | 1.367 (5) |
C23—H23B | 0.9800 | C58—H58A | 0.9500 |
C23—H23C | 0.9800 | C59—C510 | 1.396 (4) |
C31—H31A | 0.9800 | C59—H59A | 0.9500 |
C31—H31B | 0.9800 | C510—H51B | 0.9500 |
C31—H31C | 0.9800 | C511—O7 | 1.209 (3) |
C41—O3 | 1.204 (3) | C511—O8 | 1.348 (3) |
C41—O4 | 1.335 (3) | C512—O8 | 1.443 (3) |
C42—O4 | 1.452 (3) | C512—C513 | 1.512 (3) |
C42—C43 | 1.501 (4) | C512—H51C | 0.9900 |
C42—H42A | 0.9900 | C512—H51D | 0.9900 |
C42—H42B | 0.9900 | C513—C518 | 1.389 (3) |
C43—C48 | 1.386 (4) | C513—C514 | 1.391 (3) |
C43—C44 | 1.391 (4) | C514—C515 | 1.384 (4) |
C44—C45 | 1.387 (4) | C514—H51E | 0.9500 |
C44—H44A | 0.9500 | C515—C516 | 1.383 (4) |
C45—C46 | 1.380 (4) | C515—H51F | 0.9500 |
C45—H45A | 0.9500 | C516—C517 | 1.390 (4) |
C46—C47 | 1.373 (4) | C516—H51G | 0.9500 |
C46—H46A | 0.9500 | C517—C518 | 1.384 (4) |
C47—C48 | 1.385 (4) | C517—H51H | 0.9500 |
C47—H47A | 0.9500 | C518—H51I | 0.9500 |
C48—H48A | 0.9500 | | |
| | | |
C5—N1—C2 | 110.2 (2) | C41—O4—C42 | 115.66 (19) |
C5—N1—H1 | 124.4 (18) | C52—C51—C5 | 134.5 (2) |
C2—N1—H1 | 125.4 (18) | C52—C51—H51A | 112.8 |
N1—C2—C3 | 109.1 (2) | C5—C51—H51A | 112.8 |
N1—C2—C21 | 120.0 (2) | C51—C52—C53 | 124.3 (2) |
C3—C2—C21 | 130.9 (2) | C51—C52—C511 | 117.7 (2) |
C2—C3—C4 | 106.2 (2) | C53—C52—C511 | 117.9 (2) |
C2—C3—C31 | 125.1 (2) | O5—C53—O6 | 121.9 (2) |
C4—C3—C31 | 128.8 (2) | O5—C53—C52 | 125.8 (2) |
C5—C4—C3 | 107.6 (2) | O6—C53—C52 | 112.3 (2) |
C5—C4—C41 | 124.1 (2) | O6—C54—C55 | 107.1 (2) |
C3—C4—C41 | 128.2 (2) | O6—C54—H54A | 110.3 |
N1—C5—C4 | 106.9 (2) | C55—C54—H54A | 110.3 |
N1—C5—C51 | 126.1 (2) | O6—C54—H54B | 110.3 |
C4—C5—C51 | 127.0 (2) | C55—C54—H54B | 110.3 |
O1—C21—O2 | 124.3 (2) | H54A—C54—H54B | 108.6 |
O1—C21—C2 | 125.1 (2) | C510—C55—C56 | 118.5 (3) |
O2—C21—C2 | 110.5 (2) | C510—C55—C54 | 120.6 (3) |
O2—C22—C23 | 106.9 (2) | C56—C55—C54 | 120.9 (2) |
O2—C22—H22A | 110.3 | C57—C56—C55 | 120.6 (3) |
C23—C22—H22A | 110.3 | C57—C56—H56A | 119.7 |
O2—C22—H22B | 110.3 | C55—C56—H56A | 119.7 |
C23—C22—H22B | 110.3 | C58—C57—C56 | 119.9 (3) |
H22A—C22—H22B | 108.6 | C58—C57—H57A | 120.1 |
C22—C23—H23A | 109.5 | C56—C57—H57A | 120.1 |
C22—C23—H23B | 109.5 | C59—C58—C57 | 120.2 (3) |
H23A—C23—H23B | 109.5 | C59—C58—H58A | 119.9 |
C22—C23—H23C | 109.5 | C57—C58—H58A | 119.9 |
H23A—C23—H23C | 109.5 | C58—C59—C510 | 120.0 (3) |
H23B—C23—H23C | 109.5 | C58—C59—H59A | 120.0 |
C21—O2—C22 | 116.25 (19) | C510—C59—H59A | 120.0 |
C3—C31—H31A | 109.5 | C55—C510—C59 | 120.8 (3) |
C3—C31—H31B | 109.5 | C55—C510—H51B | 119.6 |
H31A—C31—H31B | 109.5 | C59—C510—H51B | 119.6 |
C3—C31—H31C | 109.5 | O7—C511—O8 | 122.2 (2) |
H31A—C31—H31C | 109.5 | O7—C511—C52 | 125.9 (2) |
H31B—C31—H31C | 109.5 | O8—C511—C52 | 111.85 (19) |
O3—C41—O4 | 121.5 (2) | O8—C512—C513 | 108.70 (19) |
O3—C41—C4 | 126.2 (2) | O8—C512—H51C | 109.9 |
O4—C41—C4 | 112.3 (2) | C513—C512—H51C | 109.9 |
O4—C42—C43 | 108.8 (2) | O8—C512—H51D | 109.9 |
O4—C42—H42A | 109.9 | C513—C512—H51D | 109.9 |
C43—C42—H42A | 109.9 | H51C—C512—H51D | 108.3 |
O4—C42—H42B | 109.9 | C518—C513—C514 | 118.8 (2) |
C43—C42—H42B | 109.9 | C518—C513—C512 | 122.3 (2) |
H42A—C42—H42B | 108.3 | C514—C513—C512 | 118.9 (2) |
C48—C43—C44 | 118.5 (3) | C515—C514—C513 | 121.0 (2) |
C48—C43—C42 | 120.4 (3) | C515—C514—H51E | 119.5 |
C44—C43—C42 | 121.1 (3) | C513—C514—H51E | 119.5 |
C45—C44—C43 | 120.6 (3) | C516—C515—C514 | 120.0 (2) |
C45—C44—H44A | 119.7 | C516—C515—H51F | 120.0 |
C43—C44—H44A | 119.7 | C514—C515—H51F | 120.0 |
C46—C45—C44 | 120.1 (3) | C515—C516—C517 | 119.3 (2) |
C46—C45—H45A | 119.9 | C515—C516—H51G | 120.4 |
C44—C45—H45A | 119.9 | C517—C516—H51G | 120.4 |
C47—C46—C45 | 119.6 (3) | C518—C517—C516 | 120.7 (2) |
C47—C46—H46A | 120.2 | C518—C517—H51H | 119.7 |
C45—C46—H46A | 120.2 | C516—C517—H51H | 119.7 |
C46—C47—C48 | 120.7 (3) | C517—C518—C513 | 120.2 (2) |
C46—C47—H47A | 119.7 | C517—C518—H51I | 119.9 |
C48—C47—H47A | 119.7 | C513—C518—H51I | 119.9 |
C47—C48—C43 | 120.5 (3) | C53—O6—C54 | 115.38 (19) |
C47—C48—H48A | 119.8 | C511—O8—C512 | 116.52 (18) |
C43—C48—H48A | 119.8 | | |
| | | |
C5—N1—C2—C3 | 0.2 (3) | C43—C42—O4—C41 | 156.7 (2) |
C5—N1—C2—C21 | −179.1 (2) | N1—C5—C51—C52 | −6.2 (4) |
N1—C2—C3—C4 | 0.2 (3) | C4—C5—C51—C52 | 174.5 (3) |
C21—C2—C3—C4 | 179.5 (2) | C5—C51—C52—C53 | 0.5 (4) |
N1—C2—C3—C31 | −179.4 (2) | C5—C51—C52—C511 | 175.9 (2) |
C21—C2—C3—C31 | −0.1 (4) | C51—C52—C53—O5 | 24.6 (4) |
C2—C3—C4—C5 | −0.6 (3) | C511—C52—C53—O5 | −150.8 (2) |
C31—C3—C4—C5 | 179.0 (2) | C51—C52—C53—O6 | −154.5 (2) |
C2—C3—C4—C41 | 177.6 (2) | C511—C52—C53—O6 | 30.1 (3) |
C31—C3—C4—C41 | −2.8 (4) | O6—C54—C55—C510 | 130.6 (3) |
C2—N1—C5—C4 | −0.6 (3) | O6—C54—C55—C56 | −49.8 (3) |
C2—N1—C5—C51 | −180.0 (2) | C510—C55—C56—C57 | 0.1 (4) |
C3—C4—C5—N1 | 0.7 (3) | C54—C55—C56—C57 | −179.5 (3) |
C41—C4—C5—N1 | −177.6 (2) | C55—C56—C57—C58 | 0.2 (5) |
C3—C4—C5—C51 | −179.9 (2) | C56—C57—C58—C59 | −0.1 (5) |
C41—C4—C5—C51 | 1.8 (4) | C57—C58—C59—C510 | −0.2 (5) |
N1—C2—C21—O1 | 176.7 (2) | C56—C55—C510—C59 | −0.4 (4) |
C3—C2—C21—O1 | −2.6 (4) | C54—C55—C510—C59 | 179.2 (3) |
N1—C2—C21—O2 | −2.8 (3) | C58—C59—C510—C55 | 0.5 (5) |
C3—C2—C21—O2 | 178.0 (2) | C51—C52—C511—O7 | −159.2 (3) |
O1—C21—O2—C22 | −4.3 (4) | C53—C52—C511—O7 | 16.4 (4) |
C2—C21—O2—C22 | 175.1 (2) | C51—C52—C511—O8 | 17.8 (3) |
C23—C22—O2—C21 | 176.8 (2) | C53—C52—C511—O8 | −166.5 (2) |
C5—C4—C41—O3 | −5.9 (4) | O8—C512—C513—C518 | −17.3 (3) |
C3—C4—C41—O3 | 176.1 (3) | O8—C512—C513—C514 | 164.4 (2) |
C5—C4—C41—O4 | 174.0 (2) | C518—C513—C514—C515 | −0.3 (4) |
C3—C4—C41—O4 | −4.0 (3) | C512—C513—C514—C515 | 178.1 (2) |
O4—C42—C43—C48 | −133.2 (3) | C513—C514—C515—C516 | 0.4 (4) |
O4—C42—C43—C44 | 49.0 (4) | C514—C515—C516—C517 | −0.3 (4) |
C48—C43—C44—C45 | −1.6 (4) | C515—C516—C517—C518 | 0.0 (4) |
C42—C43—C44—C45 | 176.2 (3) | C516—C517—C518—C513 | 0.1 (4) |
C43—C44—C45—C46 | 0.6 (5) | C514—C513—C518—C517 | 0.0 (4) |
C44—C45—C46—C47 | 0.5 (5) | C512—C513—C518—C517 | −178.3 (2) |
C45—C46—C47—C48 | −0.6 (5) | O5—C53—O6—C54 | 6.2 (3) |
C46—C47—C48—C43 | −0.4 (5) | C52—C53—O6—C54 | −174.7 (2) |
C44—C43—C48—C47 | 1.5 (4) | C55—C54—O6—C53 | 172.9 (2) |
C42—C43—C48—C47 | −176.4 (3) | O7—C511—O8—C512 | 7.8 (3) |
O3—C41—O4—C42 | 2.6 (4) | C52—C511—O8—C512 | −169.39 (19) |
C4—C41—O4—C42 | −177.3 (2) | C513—C512—O8—C511 | 175.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5 | 0.91 (3) | 1.89 (3) | 2.668 (3) | 142 (2) |
C22—H22B···O1i | 0.99 | 2.59 | 3.570 (3) | 171 |
C515—H51F···O1ii | 0.95 | 2.50 | 3.445 (3) | 173 |
C518—H51I···O3 | 0.95 | 2.42 | 3.297 (3) | 154 |
C518—H51I···O8 | 0.95 | 2.41 | 2.750 (3) | 101 |
C51—H51A···O3 | 0.95 | 2.27 | 2.961 (3) | 129 |
C51—H51A···O8 | 0.95 | 2.18 | 2.655 (3) | 110 |
C31—H31A···O1 | 0.98 | 2.38 | 3.109 (3) | 131 |
C31—H31B···O4 | 0.98 | 2.53 | 2.859 (3) | 100 |
C54—H54A···Cg | 0.99 | 2.69 | 3.607 (3) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y−1, z. |