The molecule of the title compound, C
30H
48N
4O
4, displays approximate twofold symmetry. The four amide groups are arranged such that four intramolecular N—H
O hydrogen bonds are formed.
Supporting information
CCDC reference: 221674
Key indicators
- Single-crystal X-ray study
- T = 143 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.103
- Data-to-parameter ratio = 17.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_320 Alert C Check Hybridisation of C5 in Main Residue . ?
PLAT_320 Alert C Check Hybridisation of C7 in Main Residue . ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
3-Isopropylidene-tetracyclo[3.2.0.0
2,7.0
4,5]heptane- 1,5,6,7-tetracarboxylic
acid tetrakis(
tert-butylamide)
top
Crystal data top
C30H48N4O4 | Z = 2 |
Mr = 528.72 | F(000) = 576 |
Triclinic, P1 | Dx = 1.127 Mg m−3 |
a = 9.9831 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.2324 (10) Å | Cell parameters from 5756 reflections |
c = 13.9644 (10) Å | θ = 2–28° |
α = 92.574 (3)° | µ = 0.08 mm−1 |
β = 106.831 (3)° | T = 143 K |
γ = 105.554 (3)° | Prism, colourless |
V = 1558.5 (2) Å3 | 0.40 × 0.29 × 0.17 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 4684 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.4°, θmin = 1.5° |
Detector resolution: 8.192 pixels mm-1 | h = −12→12 |
ω–scan | k = −15→15 |
14409 measured reflections | l = −17→17 |
6352 independent reflections | |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3 |
6352 reflections | (Δ/σ)max < 0.001 |
373 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.18 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 | |
O1 | 0.60747 (11) | 0.47639 (8) | 0.64218 (8) | 0.0417 (3) | |
O2 | 0.43366 (10) | 0.10456 (7) | 0.70203 (7) | 0.0356 (2) | |
O3 | 0.17048 (11) | 0.23915 (8) | 0.87880 (7) | 0.0347 (2) | |
O4 | 0.28301 (11) | 0.59070 (7) | 0.77216 (7) | 0.0351 (2) | |
N1 | 0.49918 (15) | 0.60357 (9) | 0.68437 (9) | 0.0370 (3) | |
H01 | 0.4307 (18) | 0.6122 (13) | 0.7077 (12) | 0.045 (5)* | |
N2 | 0.60441 (12) | 0.26198 (10) | 0.68533 (8) | 0.0309 (3) | |
H02 | 0.6165 (16) | 0.3373 (14) | 0.6724 (11) | 0.042 (4)* | |
N3 | 0.25743 (12) | 0.10357 (9) | 0.82410 (9) | 0.0295 (3) | |
H03 | 0.3045 (17) | 0.0890 (12) | 0.7853 (11) | 0.036 (4)* | |
N4 | 0.26571 (12) | 0.47241 (9) | 0.89138 (8) | 0.0261 (2) | |
H04 | 0.2378 (15) | 0.3975 (13) | 0.8985 (11) | 0.034 (4)* | |
C1 | 0.37739 (14) | 0.40315 (10) | 0.66910 (9) | 0.0259 (3) | |
C2 | 0.21965 (14) | 0.40172 (11) | 0.61595 (9) | 0.0269 (3) | |
H2 | 0.1981 | 0.4715 | 0.5886 | 0.032* | |
C3 | 0.13231 (14) | 0.28643 (11) | 0.56195 (9) | 0.0268 (3) | |
C4 | 0.20270 (13) | 0.21392 (11) | 0.62881 (9) | 0.0256 (3) | |
H4 | 0.1666 | 0.1286 | 0.6122 | 0.031* | |
C5 | 0.36551 (13) | 0.27441 (10) | 0.67752 (9) | 0.0250 (3) | |
C6 | 0.25752 (13) | 0.26996 (10) | 0.73879 (9) | 0.0241 (3) | |
C7 | 0.26756 (13) | 0.39779 (10) | 0.72941 (9) | 0.0245 (3) | |
C8 | 0.02138 (15) | 0.25601 (12) | 0.47614 (10) | 0.0336 (3) | |
C9 | −0.05601 (18) | 0.13288 (13) | 0.43273 (11) | 0.0448 (4) | |
H9A | −0.0320 | 0.1157 | 0.3716 | 0.054* | |
H9B | −0.1620 | 0.1192 | 0.4159 | 0.054* | |
H9C | −0.0245 | 0.0834 | 0.4824 | 0.054* | |
C10 | −0.03578 (19) | 0.34118 (14) | 0.41501 (12) | 0.0501 (4) | |
H10A | 0.0248 | 0.4189 | 0.4459 | 0.060* | |
H10B | −0.1371 | 0.3320 | 0.4131 | 0.060* | |
H10C | −0.0324 | 0.3282 | 0.3461 | 0.060* | |
C11 | 0.50598 (15) | 0.49833 (11) | 0.66517 (9) | 0.0299 (3) | |
C12 | 0.60886 (19) | 0.71080 (12) | 0.68096 (11) | 0.0453 (4) | |
C13 | 0.7567 (2) | 0.71772 (17) | 0.75515 (17) | 0.0929 (9) | |
H13A | 0.7502 | 0.7201 | 0.8239 | 0.112* | |
H13B | 0.8297 | 0.7872 | 0.7502 | 0.112* | |
H13C | 0.7857 | 0.6503 | 0.7393 | 0.112* | |
C14 | 0.6179 (2) | 0.71641 (14) | 0.57472 (13) | 0.0539 (5) | |
H14A | 0.6548 | 0.6547 | 0.5561 | 0.065* | |
H14B | 0.6845 | 0.7905 | 0.5718 | 0.065* | |
H14C | 0.5203 | 0.7077 | 0.5276 | 0.065* | |
C15 | 0.5523 (3) | 0.80717 (14) | 0.71019 (15) | 0.0763 (7) | |
H15A | 0.4612 | 0.8052 | 0.6580 | 0.092* | |
H15B | 0.6257 | 0.8810 | 0.7165 | 0.092* | |
H15C | 0.5335 | 0.7974 | 0.7749 | 0.092* | |
C16 | 0.47254 (14) | 0.20635 (11) | 0.68937 (9) | 0.0275 (3) | |
C17 | 0.72657 (15) | 0.21211 (13) | 0.69405 (11) | 0.0380 (3) | |
C18 | 0.85528 (18) | 0.31059 (16) | 0.68948 (16) | 0.0623 (5) | |
H18A | 0.8279 | 0.3419 | 0.6257 | 0.075* | |
H18B | 0.9396 | 0.2824 | 0.6937 | 0.075* | |
H18C | 0.8810 | 0.3707 | 0.7461 | 0.075* | |
C19 | 0.6843 (2) | 0.11741 (15) | 0.60645 (13) | 0.0530 (4) | |
H19A | 0.5974 | 0.0574 | 0.6077 | 0.064* | |
H19B | 0.7655 | 0.0848 | 0.6129 | 0.064* | |
H19C | 0.6628 | 0.1493 | 0.5425 | 0.064* | |
C20 | 0.76546 (18) | 0.16537 (16) | 0.79443 (12) | 0.0522 (4) | |
H20A | 0.7890 | 0.2264 | 0.8498 | 0.063* | |
H20B | 0.8504 | 0.1371 | 0.8013 | 0.063* | |
H20C | 0.6820 | 0.1025 | 0.7967 | 0.063* | |
C21 | 0.22703 (13) | 0.20304 (10) | 0.82121 (9) | 0.0250 (3) | |
C22 | 0.22689 (15) | 0.02095 (11) | 0.89486 (10) | 0.0327 (3) | |
C23 | 0.3111 (2) | 0.07463 (14) | 1.00274 (12) | 0.0579 (5) | |
H23A | 0.4162 | 0.0989 | 1.0113 | 0.069* | |
H23B | 0.2911 | 0.0185 | 1.0486 | 0.069* | |
H23C | 0.2805 | 0.1413 | 1.0183 | 0.069* | |
C24 | 0.06388 (17) | −0.01849 (14) | 0.88008 (14) | 0.0526 (4) | |
H24A | 0.0337 | 0.0453 | 0.9029 | 0.063* | |
H24B | 0.0423 | −0.0815 | 0.9194 | 0.063* | |
H24C | 0.0102 | −0.0447 | 0.8084 | 0.063* | |
C25 | 0.2765 (2) | −0.08014 (14) | 0.86738 (14) | 0.0584 (5) | |
H25A | 0.2157 | −0.1174 | 0.7992 | 0.070* | |
H25B | 0.2665 | −0.1351 | 0.9157 | 0.070* | |
H25C | 0.3792 | −0.0529 | 0.8696 | 0.070* | |
C26 | 0.27135 (13) | 0.49490 (10) | 0.80019 (9) | 0.0258 (3) | |
C27 | 0.26760 (14) | 0.55655 (11) | 0.97165 (10) | 0.0293 (3) | |
C28 | 0.40649 (15) | 0.65728 (12) | 0.99792 (11) | 0.0386 (3) | |
H28A | 0.4924 | 0.6291 | 1.0182 | 0.046* | |
H28B | 0.4088 | 0.7102 | 1.0536 | 0.046* | |
H28C | 0.4076 | 0.6973 | 0.9388 | 0.046* | |
C29 | 0.26686 (18) | 0.49287 (13) | 1.06292 (11) | 0.0411 (4) | |
H29A | 0.1808 | 0.4253 | 1.0446 | 0.049* | |
H29B | 0.2634 | 0.5435 | 1.1180 | 0.049* | |
H29C | 0.3559 | 0.4689 | 1.0849 | 0.049* | |
C30 | 0.13083 (15) | 0.59655 (13) | 0.93642 (11) | 0.0369 (3) | |
H30A | 0.1324 | 0.6359 | 0.8770 | 0.044* | |
H30B | 0.1291 | 0.6493 | 0.9907 | 0.044* | |
H30C | 0.0433 | 0.5302 | 0.9190 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0352 (6) | 0.0344 (6) | 0.0560 (7) | 0.0060 (4) | 0.0180 (5) | 0.0118 (5) |
O2 | 0.0387 (5) | 0.0269 (5) | 0.0475 (6) | 0.0150 (4) | 0.0172 (5) | 0.0105 (4) |
O3 | 0.0436 (6) | 0.0286 (5) | 0.0371 (5) | 0.0105 (4) | 0.0202 (5) | 0.0080 (4) |
O4 | 0.0531 (6) | 0.0251 (5) | 0.0318 (5) | 0.0170 (4) | 0.0146 (5) | 0.0076 (4) |
N1 | 0.0546 (8) | 0.0225 (6) | 0.0326 (7) | 0.0023 (6) | 0.0199 (6) | 0.0048 (5) |
N2 | 0.0299 (6) | 0.0304 (6) | 0.0344 (6) | 0.0116 (5) | 0.0102 (5) | 0.0060 (5) |
N3 | 0.0331 (6) | 0.0264 (6) | 0.0310 (6) | 0.0105 (5) | 0.0106 (5) | 0.0103 (5) |
N4 | 0.0310 (6) | 0.0225 (6) | 0.0247 (6) | 0.0091 (5) | 0.0075 (5) | 0.0033 (4) |
C1 | 0.0303 (7) | 0.0228 (6) | 0.0230 (6) | 0.0074 (5) | 0.0064 (5) | 0.0040 (5) |
C2 | 0.0336 (7) | 0.0240 (6) | 0.0230 (6) | 0.0116 (5) | 0.0055 (5) | 0.0063 (5) |
C3 | 0.0307 (7) | 0.0250 (6) | 0.0252 (7) | 0.0106 (5) | 0.0073 (5) | 0.0038 (5) |
C4 | 0.0271 (7) | 0.0221 (6) | 0.0252 (7) | 0.0069 (5) | 0.0050 (5) | 0.0028 (5) |
C5 | 0.0271 (7) | 0.0219 (6) | 0.0248 (6) | 0.0072 (5) | 0.0063 (5) | 0.0041 (5) |
C6 | 0.0238 (6) | 0.0225 (6) | 0.0244 (6) | 0.0072 (5) | 0.0045 (5) | 0.0040 (5) |
C7 | 0.0282 (7) | 0.0226 (6) | 0.0226 (6) | 0.0088 (5) | 0.0058 (5) | 0.0058 (5) |
C8 | 0.0370 (8) | 0.0338 (7) | 0.0275 (7) | 0.0141 (6) | 0.0035 (6) | 0.0013 (6) |
C9 | 0.0465 (9) | 0.0399 (9) | 0.0350 (8) | 0.0122 (7) | −0.0049 (7) | −0.0032 (7) |
C10 | 0.0621 (11) | 0.0454 (9) | 0.0338 (8) | 0.0252 (8) | −0.0070 (8) | 0.0036 (7) |
C11 | 0.0343 (7) | 0.0275 (7) | 0.0217 (6) | 0.0039 (6) | 0.0043 (6) | 0.0046 (5) |
C12 | 0.0654 (11) | 0.0246 (7) | 0.0311 (8) | −0.0067 (7) | 0.0110 (7) | 0.0054 (6) |
C13 | 0.0863 (16) | 0.0510 (12) | 0.0777 (15) | −0.0306 (11) | −0.0245 (12) | 0.0175 (11) |
C14 | 0.0733 (12) | 0.0411 (9) | 0.0480 (10) | 0.0039 (8) | 0.0307 (9) | 0.0146 (8) |
C15 | 0.142 (2) | 0.0254 (9) | 0.0626 (12) | 0.0041 (10) | 0.0536 (13) | 0.0041 (8) |
C16 | 0.0307 (7) | 0.0288 (7) | 0.0231 (6) | 0.0115 (6) | 0.0062 (5) | 0.0024 (5) |
C17 | 0.0333 (8) | 0.0446 (8) | 0.0429 (8) | 0.0199 (7) | 0.0143 (6) | 0.0065 (7) |
C18 | 0.0376 (9) | 0.0656 (12) | 0.0920 (15) | 0.0187 (9) | 0.0291 (10) | 0.0156 (11) |
C19 | 0.0644 (11) | 0.0609 (11) | 0.0494 (10) | 0.0344 (9) | 0.0266 (9) | 0.0074 (8) |
C20 | 0.0470 (10) | 0.0731 (12) | 0.0449 (9) | 0.0371 (9) | 0.0083 (8) | 0.0122 (9) |
C21 | 0.0219 (6) | 0.0230 (6) | 0.0247 (6) | 0.0034 (5) | 0.0021 (5) | 0.0035 (5) |
C22 | 0.0368 (8) | 0.0244 (7) | 0.0318 (7) | 0.0047 (6) | 0.0058 (6) | 0.0119 (6) |
C23 | 0.0730 (12) | 0.0404 (9) | 0.0361 (9) | −0.0009 (8) | −0.0049 (8) | 0.0175 (7) |
C24 | 0.0439 (9) | 0.0422 (9) | 0.0619 (11) | −0.0021 (7) | 0.0137 (8) | 0.0201 (8) |
C25 | 0.0827 (13) | 0.0401 (9) | 0.0656 (12) | 0.0313 (9) | 0.0276 (10) | 0.0275 (9) |
C26 | 0.0261 (6) | 0.0252 (7) | 0.0256 (7) | 0.0101 (5) | 0.0048 (5) | 0.0036 (5) |
C27 | 0.0324 (7) | 0.0299 (7) | 0.0259 (7) | 0.0110 (6) | 0.0086 (6) | 0.0002 (5) |
C28 | 0.0351 (8) | 0.0368 (8) | 0.0374 (8) | 0.0071 (6) | 0.0069 (6) | −0.0078 (6) |
C29 | 0.0519 (9) | 0.0474 (9) | 0.0293 (8) | 0.0199 (7) | 0.0157 (7) | 0.0053 (7) |
C30 | 0.0359 (8) | 0.0402 (8) | 0.0377 (8) | 0.0162 (6) | 0.0124 (6) | 0.0005 (6) |
Geometric parameters (Å, º) top
O1—C11 | 1.2362 (16) | C13—H13B | 0.9800 |
O2—C16 | 1.2379 (15) | C13—H13C | 0.9800 |
O3—C21 | 1.2350 (15) | C14—H14A | 0.9800 |
O4—C26 | 1.2387 (15) | C14—H14B | 0.9800 |
N1—C11 | 1.3267 (18) | C14—H14C | 0.9800 |
N1—C12 | 1.4789 (18) | C15—H15A | 0.9800 |
N1—H01 | 0.866 (16) | C15—H15B | 0.9800 |
N2—C16 | 1.3287 (17) | C15—H15C | 0.9800 |
N2—C17 | 1.4811 (17) | C17—C20 | 1.523 (2) |
N2—H02 | 0.930 (16) | C17—C19 | 1.526 (2) |
N3—C21 | 1.3302 (16) | C17—C18 | 1.527 (2) |
N3—C22 | 1.4799 (16) | C18—H18A | 0.9800 |
N3—H03 | 0.854 (16) | C18—H18B | 0.9800 |
N4—C26 | 1.3285 (16) | C18—H18C | 0.9800 |
N4—C27 | 1.4799 (16) | C19—H19A | 0.9800 |
N4—H04 | 0.903 (15) | C19—H19B | 0.9800 |
C1—C11 | 1.5005 (18) | C19—H19C | 0.9800 |
C1—C2 | 1.5291 (18) | C20—H20A | 0.9800 |
C1—C7 | 1.5546 (18) | C20—H20B | 0.9800 |
C1—C5 | 1.5597 (16) | C20—H20C | 0.9800 |
C2—C3 | 1.4772 (18) | C22—C23 | 1.513 (2) |
C2—C7 | 1.5237 (17) | C22—C24 | 1.516 (2) |
C2—H2 | 1.0000 | C22—C25 | 1.522 (2) |
C3—C8 | 1.3309 (18) | C23—H23A | 0.9800 |
C3—C4 | 1.4767 (17) | C23—H23B | 0.9800 |
C4—C5 | 1.5237 (17) | C23—H23C | 0.9800 |
C4—C6 | 1.5316 (17) | C24—H24A | 0.9800 |
C4—H4 | 1.0000 | C24—H24B | 0.9800 |
C5—C16 | 1.4998 (17) | C24—H24C | 0.9800 |
C5—C6 | 1.5505 (17) | C25—H25A | 0.9800 |
C6—C21 | 1.4971 (17) | C25—H25B | 0.9800 |
C6—C7 | 1.5537 (16) | C25—H25C | 0.9800 |
C7—C26 | 1.4961 (17) | C27—C29 | 1.5241 (19) |
C8—C9 | 1.502 (2) | C27—C28 | 1.5245 (19) |
C8—C10 | 1.5021 (19) | C27—C30 | 1.5285 (19) |
C9—H9A | 0.9800 | C28—H28A | 0.9800 |
C9—H9B | 0.9800 | C28—H28B | 0.9800 |
C9—H9C | 0.9800 | C28—H28C | 0.9800 |
C10—H10A | 0.9800 | C29—H29A | 0.9800 |
C10—H10B | 0.9800 | C29—H29B | 0.9800 |
C10—H10C | 0.9800 | C29—H29C | 0.9800 |
C12—C14 | 1.516 (2) | C30—H30A | 0.9800 |
C12—C13 | 1.516 (3) | C30—H30B | 0.9800 |
C12—C15 | 1.524 (2) | C30—H30C | 0.9800 |
C13—H13A | 0.9800 | | |
| | | |
C11—N1—C12 | 125.83 (14) | C12—C15—H15A | 109.5 |
C11—N1—H01 | 118.4 (11) | C12—C15—H15B | 109.5 |
C12—N1—H01 | 115.3 (11) | H15A—C15—H15B | 109.5 |
C16—N2—C17 | 125.57 (12) | C12—C15—H15C | 109.5 |
C16—N2—H02 | 115.3 (9) | H15A—C15—H15C | 109.5 |
C17—N2—H02 | 119.1 (9) | H15B—C15—H15C | 109.5 |
C21—N3—C22 | 125.12 (12) | O2—C16—N2 | 124.86 (12) |
C21—N3—H03 | 117.1 (10) | O2—C16—C5 | 119.03 (11) |
C22—N3—H03 | 117.6 (10) | N2—C16—C5 | 116.11 (11) |
C26—N4—C27 | 124.96 (11) | N2—C17—C20 | 110.13 (12) |
C26—N4—H04 | 115.6 (9) | N2—C17—C19 | 109.98 (12) |
C27—N4—H04 | 117.9 (9) | C20—C17—C19 | 110.40 (13) |
C11—C1—C2 | 121.94 (11) | N2—C17—C18 | 105.64 (12) |
C11—C1—C7 | 131.31 (11) | C20—C17—C18 | 110.12 (14) |
C2—C1—C7 | 59.22 (8) | C19—C17—C18 | 110.46 (14) |
C11—C1—C5 | 128.87 (11) | C17—C18—H18A | 109.5 |
C2—C1—C5 | 103.65 (10) | C17—C18—H18B | 109.5 |
C7—C1—C5 | 90.15 (9) | H18A—C18—H18B | 109.5 |
C3—C2—C7 | 110.03 (10) | C17—C18—H18C | 109.5 |
C3—C2—C1 | 110.17 (10) | H18A—C18—H18C | 109.5 |
C7—C2—C1 | 61.23 (8) | H18B—C18—H18C | 109.5 |
C3—C2—H2 | 120.4 | C17—C19—H19A | 109.5 |
C7—C2—H2 | 120.4 | C17—C19—H19B | 109.5 |
C1—C2—H2 | 120.4 | H19A—C19—H19B | 109.5 |
C8—C3—C4 | 129.46 (12) | C17—C19—H19C | 109.5 |
C8—C3—C2 | 129.68 (12) | H19A—C19—H19C | 109.5 |
C4—C3—C2 | 100.86 (10) | H19B—C19—H19C | 109.5 |
C3—C4—C5 | 110.45 (10) | C17—C20—H20A | 109.5 |
C3—C4—C6 | 110.26 (10) | C17—C20—H20B | 109.5 |
C5—C4—C6 | 60.99 (8) | H20A—C20—H20B | 109.5 |
C3—C4—H4 | 120.3 | C17—C20—H20C | 109.5 |
C5—C4—H4 | 120.3 | H20A—C20—H20C | 109.5 |
C6—C4—H4 | 120.3 | H20B—C20—H20C | 109.5 |
C16—C5—C4 | 119.22 (10) | O3—C21—N3 | 123.94 (12) |
C16—C5—C6 | 126.12 (10) | O3—C21—C6 | 119.61 (11) |
C4—C5—C6 | 59.76 (8) | N3—C21—C6 | 116.36 (11) |
C16—C5—C1 | 133.63 (11) | N3—C22—C23 | 110.44 (11) |
C4—C5—C1 | 103.53 (10) | N3—C22—C24 | 109.76 (11) |
C6—C5—C1 | 89.62 (9) | C23—C22—C24 | 110.46 (14) |
C21—C6—C4 | 121.26 (10) | N3—C22—C25 | 105.83 (12) |
C21—C6—C5 | 133.07 (10) | C23—C22—C25 | 110.59 (13) |
C4—C6—C5 | 59.25 (8) | C24—C22—C25 | 109.66 (13) |
C21—C6—C7 | 128.32 (11) | C22—C23—H23A | 109.5 |
C4—C6—C7 | 103.36 (9) | C22—C23—H23B | 109.5 |
C5—C6—C7 | 90.53 (9) | H23A—C23—H23B | 109.5 |
C26—C7—C2 | 119.96 (10) | C22—C23—H23C | 109.5 |
C26—C7—C6 | 133.30 (11) | H23A—C23—H23C | 109.5 |
C2—C7—C6 | 104.02 (10) | H23B—C23—H23C | 109.5 |
C26—C7—C1 | 124.74 (11) | C22—C24—H24A | 109.5 |
C2—C7—C1 | 59.56 (8) | C22—C24—H24B | 109.5 |
C6—C7—C1 | 89.69 (9) | H24A—C24—H24B | 109.5 |
C3—C8—C9 | 122.18 (12) | C22—C24—H24C | 109.5 |
C3—C8—C10 | 123.03 (13) | H24A—C24—H24C | 109.5 |
C9—C8—C10 | 114.79 (12) | H24B—C24—H24C | 109.5 |
C8—C9—H9A | 109.5 | C22—C25—H25A | 109.5 |
C8—C9—H9B | 109.5 | C22—C25—H25B | 109.5 |
H9A—C9—H9B | 109.5 | H25A—C25—H25B | 109.5 |
C8—C9—H9C | 109.5 | C22—C25—H25C | 109.5 |
H9A—C9—H9C | 109.5 | H25A—C25—H25C | 109.5 |
H9B—C9—H9C | 109.5 | H25B—C25—H25C | 109.5 |
C8—C10—H10A | 109.5 | O4—C26—N4 | 124.08 (12) |
C8—C10—H10B | 109.5 | O4—C26—C7 | 119.07 (11) |
H10A—C10—H10B | 109.5 | N4—C26—C7 | 116.82 (11) |
C8—C10—H10C | 109.5 | N4—C27—C29 | 105.65 (11) |
H10A—C10—H10C | 109.5 | N4—C27—C28 | 110.38 (11) |
H10B—C10—H10C | 109.5 | C29—C27—C28 | 109.59 (12) |
O1—C11—N1 | 124.05 (13) | N4—C27—C30 | 109.21 (11) |
O1—C11—C1 | 120.21 (12) | C29—C27—C30 | 110.74 (12) |
N1—C11—C1 | 115.71 (13) | C28—C27—C30 | 111.13 (11) |
N1—C12—C14 | 110.00 (12) | C27—C28—H28A | 109.5 |
N1—C12—C13 | 109.94 (13) | C27—C28—H28B | 109.5 |
C14—C12—C13 | 110.85 (17) | H28A—C28—H28B | 109.5 |
N1—C12—C15 | 105.49 (14) | C27—C28—H28C | 109.5 |
C14—C12—C15 | 109.47 (13) | H28A—C28—H28C | 109.5 |
C13—C12—C15 | 110.95 (16) | H28B—C28—H28C | 109.5 |
C12—C13—H13A | 109.5 | C27—C29—H29A | 109.5 |
C12—C13—H13B | 109.5 | C27—C29—H29B | 109.5 |
H13A—C13—H13B | 109.5 | H29A—C29—H29B | 109.5 |
C12—C13—H13C | 109.5 | C27—C29—H29C | 109.5 |
H13A—C13—H13C | 109.5 | H29A—C29—H29C | 109.5 |
H13B—C13—H13C | 109.5 | H29B—C29—H29C | 109.5 |
C12—C14—H14A | 109.5 | C27—C30—H30A | 109.5 |
C12—C14—H14B | 109.5 | C27—C30—H30B | 109.5 |
H14A—C14—H14B | 109.5 | H30A—C30—H30B | 109.5 |
C12—C14—H14C | 109.5 | C27—C30—H30C | 109.5 |
H14A—C14—H14C | 109.5 | H30A—C30—H30C | 109.5 |
H14B—C14—H14C | 109.5 | H30B—C30—H30C | 109.5 |
| | | |
C11—C1—C2—C3 | 135.33 (12) | C2—C1—C7—C26 | −107.30 (13) |
C7—C1—C2—C3 | −102.39 (11) | C5—C1—C7—C26 | 146.85 (11) |
C5—C1—C2—C3 | −20.52 (13) | C11—C1—C7—C2 | 107.24 (15) |
C11—C1—C2—C7 | −122.28 (13) | C5—C1—C7—C2 | −105.85 (10) |
C5—C1—C2—C7 | 81.87 (10) | C11—C1—C7—C6 | −146.25 (13) |
C7—C2—C3—C8 | 147.41 (14) | C2—C1—C7—C6 | 106.51 (9) |
C1—C2—C3—C8 | −146.91 (14) | C5—C1—C7—C6 | 0.66 (9) |
C7—C2—C3—C4 | −33.09 (13) | C4—C3—C8—C9 | 1.3 (2) |
C1—C2—C3—C4 | 32.58 (13) | C2—C3—C8—C9 | −179.38 (14) |
C8—C3—C4—C5 | 146.62 (14) | C4—C3—C8—C10 | −178.44 (14) |
C2—C3—C4—C5 | −32.87 (13) | C2—C3—C8—C10 | 0.9 (2) |
C8—C3—C4—C6 | −147.83 (14) | C12—N1—C11—O1 | 0.5 (2) |
C2—C3—C4—C6 | 32.67 (13) | C12—N1—C11—C1 | −177.32 (12) |
C3—C4—C5—C16 | −140.42 (11) | C2—C1—C11—O1 | −130.25 (13) |
C6—C4—C5—C16 | 117.11 (12) | C7—C1—C11—O1 | 154.52 (13) |
C3—C4—C5—C6 | 102.46 (11) | C5—C1—C11—O1 | 19.0 (2) |
C3—C4—C5—C1 | 20.98 (13) | C2—C1—C11—N1 | 47.65 (17) |
C6—C4—C5—C1 | −81.48 (10) | C7—C1—C11—N1 | −27.58 (19) |
C11—C1—C5—C16 | 3.6 (2) | C5—C1—C11—N1 | −163.06 (12) |
C2—C1—C5—C16 | 157.16 (13) | C11—N1—C12—C14 | 62.8 (2) |
C7—C1—C5—C16 | −144.58 (14) | C11—N1—C12—C13 | −59.5 (2) |
C11—C1—C5—C4 | −153.75 (12) | C11—N1—C12—C15 | −179.19 (15) |
C2—C1—C5—C4 | −0.23 (12) | C17—N2—C16—O2 | 0.7 (2) |
C7—C1—C5—C4 | 58.03 (10) | C17—N2—C16—C5 | −179.33 (12) |
C11—C1—C5—C6 | 147.56 (13) | C4—C5—C16—O2 | −31.00 (17) |
C2—C1—C5—C6 | −58.92 (10) | C6—C5—C16—O2 | 41.16 (18) |
C7—C1—C5—C6 | −0.66 (9) | C1—C5—C16—O2 | 174.36 (12) |
C3—C4—C6—C21 | 132.58 (12) | C4—C5—C16—N2 | 149.03 (11) |
C5—C4—C6—C21 | −124.64 (13) | C6—C5—C16—N2 | −138.80 (12) |
C3—C4—C6—C5 | −102.78 (11) | C1—C5—C16—N2 | −5.6 (2) |
C3—C4—C6—C7 | −20.27 (13) | C16—N2—C17—C20 | −58.67 (18) |
C5—C4—C6—C7 | 82.51 (9) | C16—N2—C17—C19 | 63.23 (18) |
C16—C5—C6—C21 | −0.2 (2) | C16—N2—C17—C18 | −177.55 (14) |
C4—C5—C6—C21 | 105.69 (15) | C22—N3—C21—O3 | 0.9 (2) |
C1—C5—C6—C21 | −148.37 (13) | C22—N3—C21—C6 | −175.86 (11) |
C16—C5—C6—C4 | −105.91 (13) | C4—C6—C21—O3 | −127.28 (13) |
C1—C5—C6—C4 | 105.94 (9) | C5—C6—C21—O3 | 157.28 (13) |
C16—C5—C6—C7 | 148.81 (12) | C7—C6—C21—O3 | 18.26 (19) |
C4—C5—C6—C7 | −105.28 (9) | C4—C6—C21—N3 | 49.60 (16) |
C1—C5—C6—C7 | 0.66 (9) | C5—C6—C21—N3 | −25.85 (19) |
C3—C2—C7—C26 | −142.28 (12) | C7—C6—C21—N3 | −164.86 (11) |
C1—C2—C7—C26 | 115.10 (13) | C21—N3—C22—C23 | −61.86 (18) |
C3—C2—C7—C6 | 21.43 (13) | C21—N3—C22—C24 | 60.16 (17) |
C1—C2—C7—C6 | −81.19 (10) | C21—N3—C22—C25 | 178.42 (13) |
C3—C2—C7—C1 | 102.62 (11) | C27—N4—C26—O4 | 2.1 (2) |
C21—C6—C7—C26 | 9.6 (2) | C27—N4—C26—C7 | −179.76 (11) |
C4—C6—C7—C26 | 159.82 (13) | C2—C7—C26—O4 | −23.46 (18) |
C5—C6—C7—C26 | −141.74 (14) | C6—C7—C26—O4 | 178.49 (12) |
C21—C6—C7—C2 | −150.87 (12) | C1—C7—C26—O4 | 48.36 (17) |
C4—C6—C7—C2 | −0.68 (12) | C2—C7—C26—N4 | 158.29 (11) |
C5—C6—C7—C2 | 57.76 (10) | C6—C7—C26—N4 | 0.2 (2) |
C21—C6—C7—C1 | 150.71 (12) | C1—C7—C26—N4 | −129.89 (13) |
C4—C6—C7—C1 | −59.11 (10) | C26—N4—C27—C29 | −177.27 (12) |
C5—C6—C7—C1 | −0.66 (9) | C26—N4—C27—C28 | −58.87 (16) |
C11—C1—C7—C26 | −0.1 (2) | C26—N4—C27—C30 | 63.58 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O4 | 0.866 (16) | 1.906 (17) | 2.7481 (17) | 163.7 (15) |
N2—H02···O1 | 0.930 (16) | 1.790 (16) | 2.7116 (15) | 170.5 (14) |
N3—H03···O2 | 0.854 (16) | 1.951 (16) | 2.7799 (16) | 163.2 (14) |
N4—H04···O3 | 0.903 (15) | 1.851 (15) | 2.7350 (14) | 165.8 (13) |