The molecule of the title compound, C
38H
56N
4O
4, displays approximate twofold symmetry. The four amide groups are arranged such that four intramolecular N—H
O hydrogen bonds are formed. The molecules are linked into dimers by bifurcated (C—H)
2O interactions.
Supporting information
CCDC reference: 221671
Key indicators
- Single-crystal X-ray study
- T = 143 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_320 Alert C Check Hybridisation of C1 in Main Residue . ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 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-isopropylidenetetracyclo[3.2.0.0
2,7.0
4,5]heptane- 1,5,6,7-tetracarboxylic
acid tetrakis(cyclohexylamide)
top
Crystal data top
C38H56N4O4 | Z = 2 |
Mr = 632.87 | F(000) = 688 |
Triclinic, P1 | Dx = 1.208 Mg m−3 |
a = 10.1995 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6467 (16) Å | Cell parameters from 6008 reflections |
c = 15.206 (2) Å | θ = 2–28° |
α = 87.126 (3)° | µ = 0.08 mm−1 |
β = 77.132 (3)° | T = 143 K |
γ = 81.300 (3)° | Tablet, colourless |
V = 1740.5 (4) Å3 | 0.38 × 0.33 × 0.19 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 5126 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.4°, θmin = 1.4° |
Detector resolution: 8.192 pixels mm-1 | h = −12→12 |
ω scans | k = −14→14 |
15921 measured reflections | l = −19→19 |
7098 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1495P] where P = (Fo2 + 2Fc2)/3 |
7098 reflections | (Δ/σ)max = 0.001 |
433 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. 3-Isopropylidene-tetracyclo[3.2.0.02,7.04,5]heptane- 1,5,6,7-tetracarboxylic
acid tetrakis(cyclohexylamide) |
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 | 0.15459 (11) | 0.39917 (8) | 0.16088 (7) | 0.0287 (2) | |
O2 | 0.34661 (11) | 0.20025 (8) | 0.38288 (7) | 0.0292 (2) | |
O3 | 0.61172 (10) | 0.49388 (8) | 0.38177 (6) | 0.0249 (2) | |
O4 | 0.42131 (10) | 0.68948 (9) | 0.15772 (7) | 0.0290 (2) | |
N1 | 0.22496 (12) | 0.24171 (10) | 0.24092 (8) | 0.0237 (3) | |
H01 | 0.2594 (18) | 0.2184 (15) | 0.2895 (12) | 0.041 (5)* | |
N2 | 0.51995 (12) | 0.27909 (11) | 0.41313 (8) | 0.0254 (3) | |
H02 | 0.5586 (17) | 0.3438 (16) | 0.4091 (11) | 0.038 (5)* | |
N3 | 0.59840 (12) | 0.62321 (11) | 0.26646 (8) | 0.0251 (3) | |
H03 | 0.5415 (17) | 0.6567 (14) | 0.2296 (11) | 0.034 (4)* | |
N4 | 0.28627 (12) | 0.58752 (10) | 0.10339 (7) | 0.0225 (3) | |
H04 | 0.2337 (19) | 0.5252 (16) | 0.1158 (12) | 0.047 (5)* | |
C1 | 0.25948 (13) | 0.42979 (12) | 0.28042 (9) | 0.0203 (3) | |
C2 | 0.17811 (14) | 0.54797 (11) | 0.30926 (9) | 0.0198 (3) | |
H2 | 0.0987 | 0.5802 | 0.2827 | 0.024* | |
C3 | 0.17503 (13) | 0.56681 (11) | 0.40519 (9) | 0.0189 (3) | |
C4 | 0.30991 (13) | 0.50526 (11) | 0.41309 (9) | 0.0191 (3) | |
H4 | 0.3394 | 0.5026 | 0.4717 | 0.023* | |
C5 | 0.35107 (14) | 0.40152 (11) | 0.35031 (9) | 0.0199 (3) | |
C6 | 0.41198 (13) | 0.51615 (12) | 0.32369 (8) | 0.0203 (3) | |
C7 | 0.32190 (14) | 0.54361 (12) | 0.25335 (9) | 0.0204 (3) | |
C8 | 0.07612 (14) | 0.62359 (11) | 0.46717 (9) | 0.0212 (3) | |
C9 | 0.08406 (15) | 0.63024 (13) | 0.56416 (9) | 0.0258 (3) | |
H9A | 0.1723 | 0.5903 | 0.5724 | 0.031* | |
H9B | 0.0113 | 0.5929 | 0.6026 | 0.031* | |
H9C | 0.0738 | 0.7118 | 0.5808 | 0.031* | |
C10 | −0.05349 (15) | 0.68437 (13) | 0.44507 (10) | 0.0295 (3) | |
H10A | −0.0458 | 0.6843 | 0.3797 | 0.035* | |
H10B | −0.0701 | 0.7647 | 0.4658 | 0.035* | |
H10C | −0.1292 | 0.6438 | 0.4753 | 0.035* | |
C11 | 0.20902 (13) | 0.35430 (12) | 0.22199 (9) | 0.0200 (3) | |
C12 | 0.18365 (14) | 0.15460 (12) | 0.19075 (9) | 0.0239 (3) | |
H12 | 0.1640 | 0.1912 | 0.1333 | 0.029* | |
C13 | 0.30049 (16) | 0.05515 (13) | 0.16765 (11) | 0.0333 (4) | |
H13A | 0.3289 | 0.0252 | 0.2236 | 0.040* | |
H13B | 0.3789 | 0.0846 | 0.1272 | 0.040* | |
C14 | 0.26051 (17) | −0.04366 (14) | 0.12184 (12) | 0.0378 (4) | |
H14A | 0.2435 | −0.0164 | 0.0621 | 0.045* | |
H14B | 0.3365 | −0.1088 | 0.1121 | 0.045* | |
C15 | 0.13397 (18) | −0.08646 (13) | 0.17825 (11) | 0.0374 (4) | |
H15A | 0.1080 | −0.1477 | 0.1454 | 0.045* | |
H15B | 0.1534 | −0.1207 | 0.2357 | 0.045* | |
C16 | 0.01751 (17) | 0.01281 (14) | 0.19792 (11) | 0.0356 (4) | |
H16A | −0.0628 | −0.0159 | 0.2368 | 0.043* | |
H16B | −0.0072 | 0.0423 | 0.1407 | 0.043* | |
C17 | 0.05586 (16) | 0.11165 (13) | 0.24489 (10) | 0.0306 (3) | |
H17A | −0.0201 | 0.1768 | 0.2536 | 0.037* | |
H17B | 0.0705 | 0.0843 | 0.3051 | 0.037* | |
C18 | 0.40760 (14) | 0.28438 (12) | 0.38233 (8) | 0.0199 (3) | |
C19 | 0.57800 (14) | 0.17537 (12) | 0.45736 (9) | 0.0222 (3) | |
H19 | 0.5069 | 0.1231 | 0.4756 | 0.027* | |
C20 | 0.70010 (16) | 0.10923 (13) | 0.39436 (10) | 0.0295 (3) | |
H20A | 0.7675 | 0.1623 | 0.3707 | 0.035* | |
H20B | 0.6707 | 0.0811 | 0.3425 | 0.035* | |
C21 | 0.76632 (17) | 0.00616 (14) | 0.44261 (10) | 0.0342 (4) | |
H21A | 0.7033 | −0.0522 | 0.4583 | 0.041* | |
H21B | 0.8497 | −0.0305 | 0.4013 | 0.041* | |
C22 | 0.80250 (17) | 0.04123 (15) | 0.52738 (12) | 0.0401 (4) | |
H22A | 0.8748 | 0.0914 | 0.5112 | 0.048* | |
H22B | 0.8383 | −0.0290 | 0.5589 | 0.048* | |
C23 | 0.68006 (19) | 0.10589 (14) | 0.58981 (11) | 0.0390 (4) | |
H23A | 0.7079 | 0.1322 | 0.6429 | 0.047* | |
H23B | 0.6118 | 0.0529 | 0.6114 | 0.047* | |
C24 | 0.61671 (17) | 0.21061 (13) | 0.54174 (9) | 0.0293 (3) | |
H24A | 0.5347 | 0.2494 | 0.5832 | 0.035* | |
H24B | 0.6821 | 0.2669 | 0.5252 | 0.035* | |
C25 | 0.55041 (13) | 0.54306 (12) | 0.32541 (9) | 0.0199 (3) | |
C26 | 0.73020 (15) | 0.66198 (14) | 0.26104 (10) | 0.0312 (4) | |
H26 | 0.7704 | 0.6242 | 0.3114 | 0.037* | |
C27 | 0.71256 (19) | 0.79387 (16) | 0.27086 (12) | 0.0451 (4) | |
H27A | 0.6444 | 0.8165 | 0.3268 | 0.054* | |
H27B | 0.7999 | 0.8169 | 0.2764 | 0.054* | |
C28 | 0.6670 (2) | 0.85841 (16) | 0.19085 (16) | 0.0580 (6) | |
H28A | 0.6644 | 0.9429 | 0.1974 | 0.070* | |
H28B | 0.5741 | 0.8441 | 0.1901 | 0.070* | |
C29 | 0.7632 (2) | 0.81915 (19) | 0.10185 (14) | 0.0592 (6) | |
H29A | 0.7268 | 0.8575 | 0.0509 | 0.071* | |
H29B | 0.8530 | 0.8432 | 0.0991 | 0.071* | |
C30 | 0.77975 (18) | 0.68988 (18) | 0.09251 (11) | 0.0465 (5) | |
H30A | 0.8468 | 0.6667 | 0.0362 | 0.056* | |
H30B | 0.6919 | 0.6667 | 0.0883 | 0.056* | |
C31 | 0.82703 (16) | 0.62738 (16) | 0.17207 (11) | 0.0387 (4) | |
H31A | 0.9184 | 0.6456 | 0.1732 | 0.046* | |
H31B | 0.8346 | 0.5425 | 0.1647 | 0.046* | |
C32 | 0.34906 (14) | 0.61144 (12) | 0.16647 (9) | 0.0209 (3) | |
C33 | 0.28573 (14) | 0.65902 (12) | 0.02159 (8) | 0.0212 (3) | |
H33 | 0.2791 | 0.7420 | 0.0382 | 0.025* | |
C34 | 0.16058 (16) | 0.64622 (16) | −0.01210 (10) | 0.0366 (4) | |
H34A | 0.0788 | 0.6685 | 0.0360 | 0.044* | |
H34B | 0.1630 | 0.5639 | −0.0266 | 0.044* | |
C35 | 0.15090 (18) | 0.7216 (2) | −0.09558 (11) | 0.0500 (5) | |
H35A | 0.0724 | 0.7057 | −0.1190 | 0.060* | |
H35B | 0.1349 | 0.8044 | −0.0789 | 0.060* | |
C36 | 0.27857 (18) | 0.69924 (17) | −0.16885 (10) | 0.0420 (4) | |
H36A | 0.2866 | 0.6203 | −0.1926 | 0.050* | |
H36B | 0.2721 | 0.7557 | −0.2191 | 0.050* | |
C37 | 0.40359 (17) | 0.70969 (16) | −0.13409 (10) | 0.0396 (4) | |
H37A | 0.4013 | 0.7913 | −0.1177 | 0.048* | |
H37B | 0.4855 | 0.6886 | −0.1824 | 0.048* | |
C38 | 0.41236 (16) | 0.63067 (15) | −0.05174 (10) | 0.0341 (4) | |
H38A | 0.4221 | 0.5485 | −0.0690 | 0.041* | |
H38B | 0.4933 | 0.6414 | −0.0290 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0404 (6) | 0.0234 (5) | 0.0288 (5) | −0.0085 (5) | −0.0196 (5) | 0.0036 (4) |
O2 | 0.0373 (6) | 0.0238 (5) | 0.0317 (6) | −0.0083 (5) | −0.0171 (5) | 0.0063 (4) |
O3 | 0.0244 (5) | 0.0281 (5) | 0.0247 (5) | −0.0058 (4) | −0.0105 (4) | 0.0048 (4) |
O4 | 0.0340 (6) | 0.0294 (6) | 0.0279 (5) | −0.0096 (5) | −0.0143 (5) | 0.0079 (4) |
N1 | 0.0314 (7) | 0.0205 (6) | 0.0225 (6) | −0.0027 (5) | −0.0135 (5) | −0.0004 (5) |
N2 | 0.0256 (7) | 0.0191 (6) | 0.0340 (7) | −0.0043 (5) | −0.0127 (5) | 0.0072 (5) |
N3 | 0.0245 (7) | 0.0331 (7) | 0.0204 (6) | −0.0086 (5) | −0.0089 (5) | 0.0056 (5) |
N4 | 0.0289 (7) | 0.0229 (6) | 0.0168 (6) | −0.0061 (5) | −0.0069 (5) | 0.0039 (5) |
C1 | 0.0196 (7) | 0.0203 (7) | 0.0208 (7) | −0.0009 (5) | −0.0054 (6) | −0.0015 (5) |
C2 | 0.0209 (7) | 0.0189 (7) | 0.0204 (7) | −0.0024 (5) | −0.0067 (6) | 0.0007 (5) |
C3 | 0.0210 (7) | 0.0169 (7) | 0.0195 (7) | −0.0048 (5) | −0.0053 (5) | 0.0013 (5) |
C4 | 0.0217 (7) | 0.0197 (7) | 0.0158 (6) | −0.0036 (5) | −0.0039 (5) | 0.0011 (5) |
C5 | 0.0217 (7) | 0.0205 (7) | 0.0172 (6) | −0.0012 (6) | −0.0051 (5) | −0.0009 (5) |
C6 | 0.0208 (7) | 0.0244 (7) | 0.0150 (6) | −0.0022 (6) | −0.0031 (5) | −0.0004 (5) |
C7 | 0.0214 (7) | 0.0212 (7) | 0.0180 (7) | −0.0003 (6) | −0.0049 (6) | 0.0003 (5) |
C8 | 0.0228 (7) | 0.0182 (7) | 0.0224 (7) | −0.0040 (6) | −0.0033 (6) | −0.0008 (5) |
C9 | 0.0253 (8) | 0.0275 (8) | 0.0230 (7) | −0.0049 (6) | 0.0000 (6) | −0.0051 (6) |
C10 | 0.0255 (8) | 0.0294 (8) | 0.0301 (8) | 0.0031 (6) | −0.0031 (6) | −0.0027 (6) |
C11 | 0.0187 (7) | 0.0218 (7) | 0.0190 (7) | −0.0025 (6) | −0.0032 (5) | −0.0013 (5) |
C12 | 0.0314 (8) | 0.0198 (7) | 0.0227 (7) | −0.0042 (6) | −0.0102 (6) | −0.0015 (6) |
C13 | 0.0321 (9) | 0.0250 (8) | 0.0439 (9) | −0.0027 (7) | −0.0103 (7) | −0.0057 (7) |
C14 | 0.0411 (10) | 0.0248 (8) | 0.0470 (10) | −0.0011 (7) | −0.0085 (8) | −0.0107 (7) |
C15 | 0.0528 (11) | 0.0222 (8) | 0.0428 (10) | −0.0104 (7) | −0.0192 (8) | 0.0002 (7) |
C16 | 0.0361 (9) | 0.0336 (9) | 0.0397 (9) | −0.0130 (7) | −0.0077 (7) | −0.0033 (7) |
C17 | 0.0331 (9) | 0.0309 (8) | 0.0284 (8) | −0.0067 (7) | −0.0055 (7) | −0.0047 (6) |
C18 | 0.0232 (7) | 0.0207 (7) | 0.0148 (6) | −0.0015 (6) | −0.0028 (5) | −0.0006 (5) |
C19 | 0.0227 (7) | 0.0189 (7) | 0.0258 (7) | −0.0033 (6) | −0.0081 (6) | 0.0064 (6) |
C20 | 0.0374 (9) | 0.0261 (8) | 0.0220 (7) | 0.0024 (7) | −0.0050 (6) | 0.0011 (6) |
C21 | 0.0352 (9) | 0.0264 (8) | 0.0344 (8) | 0.0066 (7) | −0.0020 (7) | 0.0044 (7) |
C22 | 0.0382 (10) | 0.0339 (9) | 0.0522 (11) | −0.0028 (7) | −0.0240 (8) | 0.0164 (8) |
C23 | 0.0589 (11) | 0.0354 (9) | 0.0273 (8) | −0.0039 (8) | −0.0226 (8) | 0.0057 (7) |
C24 | 0.0410 (9) | 0.0248 (8) | 0.0213 (7) | −0.0020 (7) | −0.0071 (7) | 0.0006 (6) |
C25 | 0.0208 (7) | 0.0229 (7) | 0.0153 (6) | −0.0022 (6) | −0.0029 (5) | −0.0027 (5) |
C26 | 0.0307 (8) | 0.0416 (9) | 0.0267 (8) | −0.0173 (7) | −0.0118 (7) | 0.0101 (7) |
C27 | 0.0486 (11) | 0.0472 (11) | 0.0447 (10) | −0.0254 (9) | −0.0072 (8) | −0.0071 (8) |
C28 | 0.0569 (13) | 0.0299 (10) | 0.0952 (17) | −0.0139 (9) | −0.0306 (12) | 0.0101 (10) |
C29 | 0.0608 (13) | 0.0714 (14) | 0.0543 (12) | −0.0304 (11) | −0.0254 (11) | 0.0356 (11) |
C30 | 0.0386 (10) | 0.0752 (14) | 0.0286 (9) | −0.0247 (9) | −0.0038 (7) | 0.0053 (9) |
C31 | 0.0250 (8) | 0.0467 (10) | 0.0451 (10) | −0.0119 (7) | −0.0049 (7) | 0.0021 (8) |
C32 | 0.0215 (7) | 0.0207 (7) | 0.0190 (7) | −0.0001 (6) | −0.0035 (6) | 0.0011 (5) |
C33 | 0.0275 (8) | 0.0201 (7) | 0.0150 (6) | −0.0009 (6) | −0.0048 (6) | 0.0031 (5) |
C34 | 0.0281 (8) | 0.0594 (11) | 0.0224 (8) | −0.0087 (8) | −0.0067 (7) | 0.0107 (7) |
C35 | 0.0335 (10) | 0.0823 (15) | 0.0345 (9) | −0.0053 (9) | −0.0149 (8) | 0.0222 (9) |
C36 | 0.0517 (11) | 0.0560 (11) | 0.0196 (8) | −0.0109 (9) | −0.0107 (7) | 0.0109 (7) |
C37 | 0.0350 (9) | 0.0546 (11) | 0.0240 (8) | −0.0044 (8) | 0.0005 (7) | 0.0127 (8) |
C38 | 0.0256 (8) | 0.0460 (10) | 0.0261 (8) | 0.0015 (7) | −0.0031 (6) | 0.0093 (7) |
Geometric parameters (Å, º) top
O1—C11 | 1.2401 (16) | C16—H16B | 0.9900 |
O2—C18 | 1.2363 (17) | C17—H17A | 0.9900 |
O3—C25 | 1.2389 (16) | C17—H17B | 0.9900 |
O4—C32 | 1.2384 (17) | C19—C24 | 1.516 (2) |
N1—C11 | 1.3219 (18) | C19—C20 | 1.521 (2) |
N1—C12 | 1.4625 (17) | C19—H19 | 1.0000 |
N1—H01 | 0.900 (18) | C20—C21 | 1.524 (2) |
N2—C18 | 1.3233 (18) | C20—H20A | 0.9900 |
N2—C19 | 1.4635 (17) | C20—H20B | 0.9900 |
N2—H02 | 0.895 (18) | C21—C22 | 1.508 (2) |
N3—C25 | 1.3317 (18) | C21—H21A | 0.9900 |
N3—C26 | 1.4657 (19) | C21—H21B | 0.9900 |
N3—H03 | 0.927 (17) | C22—C23 | 1.512 (2) |
N4—C32 | 1.3275 (17) | C22—H22A | 0.9900 |
N4—C33 | 1.4622 (17) | C22—H22B | 0.9900 |
N4—H04 | 0.953 (19) | C23—C24 | 1.524 (2) |
C1—C11 | 1.4988 (18) | C23—H23A | 0.9900 |
C1—C2 | 1.5259 (19) | C23—H23B | 0.9900 |
C1—C7 | 1.5543 (19) | C24—H24A | 0.9900 |
C1—C5 | 1.5572 (18) | C24—H24B | 0.9900 |
C2—C3 | 1.4788 (18) | C26—C31 | 1.519 (2) |
C2—C7 | 1.5175 (19) | C26—C27 | 1.530 (2) |
C2—H2 | 1.0000 | C26—H26 | 1.0000 |
C3—C8 | 1.3343 (19) | C27—C28 | 1.522 (3) |
C3—C4 | 1.4791 (19) | C27—H27A | 0.9900 |
C4—C5 | 1.5268 (18) | C27—H27B | 0.9900 |
C4—C6 | 1.5298 (18) | C28—C29 | 1.529 (3) |
C4—H4 | 1.0000 | C28—H28A | 0.9900 |
C5—C18 | 1.5004 (18) | C28—H28B | 0.9900 |
C5—C6 | 1.5545 (19) | C29—C30 | 1.500 (3) |
C6—C25 | 1.4978 (19) | C29—H29A | 0.9900 |
C6—C7 | 1.5509 (18) | C29—H29B | 0.9900 |
C7—C32 | 1.4982 (18) | C30—C31 | 1.514 (2) |
C8—C10 | 1.5008 (19) | C30—H30A | 0.9900 |
C8—C9 | 1.5014 (19) | C30—H30B | 0.9900 |
C9—H9A | 0.9800 | C31—H31A | 0.9900 |
C9—H9B | 0.9800 | C31—H31B | 0.9900 |
C9—H9C | 0.9800 | C33—C34 | 1.507 (2) |
C10—H10A | 0.9800 | C33—C38 | 1.512 (2) |
C10—H10B | 0.9800 | C33—H33 | 1.0000 |
C10—H10C | 0.9800 | C34—C35 | 1.519 (2) |
C12—C17 | 1.518 (2) | C34—H34A | 0.9900 |
C12—C13 | 1.524 (2) | C34—H34B | 0.9900 |
C12—H12 | 1.0000 | C35—C36 | 1.512 (3) |
C13—C14 | 1.525 (2) | C35—H35A | 0.9900 |
C13—H13A | 0.9900 | C35—H35B | 0.9900 |
C13—H13B | 0.9900 | C36—C37 | 1.508 (2) |
C14—C15 | 1.519 (2) | C36—H36A | 0.9900 |
C14—H14A | 0.9900 | C36—H36B | 0.9900 |
C14—H14B | 0.9900 | C37—C38 | 1.527 (2) |
C15—C16 | 1.516 (2) | C37—H37A | 0.9900 |
C15—H15A | 0.9900 | C37—H37B | 0.9900 |
C15—H15B | 0.9900 | C38—H38A | 0.9900 |
C16—C17 | 1.527 (2) | C38—H38B | 0.9900 |
C16—H16A | 0.9900 | | |
| | | |
C11—N1—C12 | 124.02 (12) | N2—C19—H19 | 108.4 |
C11—N1—H01 | 117.3 (11) | C24—C19—H19 | 108.4 |
C12—N1—H01 | 118.6 (11) | C20—C19—H19 | 108.4 |
C18—N2—C19 | 123.04 (12) | C19—C20—C21 | 111.42 (12) |
C18—N2—H02 | 117.5 (11) | C19—C20—H20A | 109.3 |
C19—N2—H02 | 119.4 (11) | C21—C20—H20A | 109.3 |
C25—N3—C26 | 123.43 (12) | C19—C20—H20B | 109.3 |
C25—N3—H03 | 116.0 (10) | C21—C20—H20B | 109.3 |
C26—N3—H03 | 120.5 (10) | H20A—C20—H20B | 108.0 |
C32—N4—C33 | 122.40 (12) | C22—C21—C20 | 112.27 (13) |
C32—N4—H04 | 117.1 (11) | C22—C21—H21A | 109.2 |
C33—N4—H04 | 120.2 (11) | C20—C21—H21A | 109.2 |
C11—C1—C2 | 119.79 (11) | C22—C21—H21B | 109.2 |
C11—C1—C7 | 128.02 (11) | C20—C21—H21B | 109.2 |
C2—C1—C7 | 59.02 (9) | H21A—C21—H21B | 107.9 |
C11—C1—C5 | 132.38 (11) | C21—C22—C23 | 111.15 (13) |
C2—C1—C5 | 103.77 (10) | C21—C22—H22A | 109.4 |
C7—C1—C5 | 89.55 (10) | C23—C22—H22A | 109.4 |
C3—C2—C7 | 110.32 (11) | C21—C22—H22B | 109.4 |
C3—C2—C1 | 109.86 (11) | C23—C22—H22B | 109.4 |
C7—C2—C1 | 61.42 (9) | H22A—C22—H22B | 108.0 |
C3—C2—H2 | 120.4 | C22—C23—C24 | 110.96 (13) |
C7—C2—H2 | 120.4 | C22—C23—H23A | 109.4 |
C1—C2—H2 | 120.4 | C24—C23—H23A | 109.4 |
C8—C3—C2 | 128.92 (12) | C22—C23—H23B | 109.4 |
C8—C3—C4 | 130.05 (12) | C24—C23—H23B | 109.4 |
C2—C3—C4 | 101.04 (11) | H23A—C23—H23B | 108.0 |
C3—C4—C5 | 110.15 (11) | C19—C24—C23 | 111.47 (12) |
C3—C4—C6 | 109.42 (11) | C19—C24—H24A | 109.3 |
C5—C4—C6 | 61.14 (9) | C23—C24—H24A | 109.3 |
C3—C4—H4 | 120.6 | C19—C24—H24B | 109.3 |
C5—C4—H4 | 120.6 | C23—C24—H24B | 109.3 |
C6—C4—H4 | 120.6 | H24A—C24—H24B | 108.0 |
C18—C5—C4 | 121.36 (11) | O3—C25—N3 | 123.74 (13) |
C18—C5—C6 | 133.19 (12) | O3—C25—C6 | 119.69 (12) |
C4—C5—C6 | 59.53 (8) | N3—C25—C6 | 116.53 (12) |
C18—C5—C1 | 128.07 (11) | N3—C26—C31 | 110.80 (12) |
C4—C5—C1 | 103.73 (10) | N3—C26—C27 | 110.47 (13) |
C6—C5—C1 | 90.21 (10) | C31—C26—C27 | 109.57 (13) |
C25—C6—C4 | 118.91 (11) | N3—C26—H26 | 108.6 |
C25—C6—C7 | 132.13 (11) | C31—C26—H26 | 108.6 |
C4—C6—C7 | 103.97 (11) | C27—C26—H26 | 108.6 |
C25—C6—C5 | 129.19 (12) | C28—C27—C26 | 112.03 (14) |
C4—C6—C5 | 59.33 (8) | C28—C27—H27A | 109.2 |
C7—C6—C5 | 89.78 (10) | C26—C27—H27A | 109.2 |
C32—C7—C2 | 120.34 (11) | C28—C27—H27B | 109.2 |
C32—C7—C6 | 128.80 (12) | C26—C27—H27B | 109.2 |
C2—C7—C6 | 103.83 (10) | H27A—C27—H27B | 107.9 |
C32—C7—C1 | 132.80 (12) | C27—C28—C29 | 111.24 (16) |
C2—C7—C1 | 59.56 (9) | C27—C28—H28A | 109.4 |
C6—C7—C1 | 90.45 (10) | C29—C28—H28A | 109.4 |
C3—C8—C10 | 122.13 (12) | C27—C28—H28B | 109.4 |
C3—C8—C9 | 123.10 (12) | C29—C28—H28B | 109.4 |
C10—C8—C9 | 114.77 (12) | H28A—C28—H28B | 108.0 |
C8—C9—H9A | 109.5 | C30—C29—C28 | 111.36 (15) |
C8—C9—H9B | 109.5 | C30—C29—H29A | 109.4 |
H9A—C9—H9B | 109.5 | C28—C29—H29A | 109.4 |
C8—C9—H9C | 109.5 | C30—C29—H29B | 109.4 |
H9A—C9—H9C | 109.5 | C28—C29—H29B | 109.4 |
H9B—C9—H9C | 109.5 | H29A—C29—H29B | 108.0 |
C8—C10—H10A | 109.5 | C29—C30—C31 | 111.21 (15) |
C8—C10—H10B | 109.5 | C29—C30—H30A | 109.4 |
H10A—C10—H10B | 109.5 | C31—C30—H30A | 109.4 |
C8—C10—H10C | 109.5 | C29—C30—H30B | 109.4 |
H10A—C10—H10C | 109.5 | C31—C30—H30B | 109.4 |
H10B—C10—H10C | 109.5 | H30A—C30—H30B | 108.0 |
O1—C11—N1 | 124.17 (13) | C30—C31—C26 | 111.95 (14) |
O1—C11—C1 | 119.63 (12) | C30—C31—H31A | 109.2 |
N1—C11—C1 | 116.19 (12) | C26—C31—H31A | 109.2 |
N1—C12—C17 | 110.63 (11) | C30—C31—H31B | 109.2 |
N1—C12—C13 | 108.98 (12) | C26—C31—H31B | 109.2 |
C17—C12—C13 | 111.38 (12) | H31A—C31—H31B | 107.9 |
N1—C12—H12 | 108.6 | O4—C32—N4 | 123.06 (12) |
C17—C12—H12 | 108.6 | O4—C32—C7 | 120.21 (12) |
C13—C12—H12 | 108.6 | N4—C32—C7 | 116.63 (12) |
C12—C13—C14 | 111.82 (13) | N4—C33—C34 | 108.57 (12) |
C12—C13—H13A | 109.3 | N4—C33—C38 | 113.61 (11) |
C14—C13—H13A | 109.3 | C34—C33—C38 | 110.74 (12) |
C12—C13—H13B | 109.3 | N4—C33—H33 | 107.9 |
C14—C13—H13B | 109.3 | C34—C33—H33 | 107.9 |
H13A—C13—H13B | 107.9 | C38—C33—H33 | 107.9 |
C15—C14—C13 | 111.47 (13) | C33—C34—C35 | 111.46 (14) |
C15—C14—H14A | 109.3 | C33—C34—H34A | 109.3 |
C13—C14—H14A | 109.3 | C35—C34—H34A | 109.3 |
C15—C14—H14B | 109.3 | C33—C34—H34B | 109.3 |
C13—C14—H14B | 109.3 | C35—C34—H34B | 109.3 |
H14A—C14—H14B | 108.0 | H34A—C34—H34B | 108.0 |
C16—C15—C14 | 110.50 (13) | C36—C35—C34 | 111.95 (15) |
C16—C15—H15A | 109.5 | C36—C35—H35A | 109.2 |
C14—C15—H15A | 109.5 | C34—C35—H35A | 109.2 |
C16—C15—H15B | 109.5 | C36—C35—H35B | 109.2 |
C14—C15—H15B | 109.5 | C34—C35—H35B | 109.2 |
H15A—C15—H15B | 108.1 | H35A—C35—H35B | 107.9 |
C15—C16—C17 | 111.20 (13) | C37—C36—C35 | 111.54 (14) |
C15—C16—H16A | 109.4 | C37—C36—H36A | 109.3 |
C17—C16—H16A | 109.4 | C35—C36—H36A | 109.3 |
C15—C16—H16B | 109.4 | C37—C36—H36B | 109.3 |
C17—C16—H16B | 109.4 | C35—C36—H36B | 109.3 |
H16A—C16—H16B | 108.0 | H36A—C36—H36B | 108.0 |
C12—C17—C16 | 111.79 (12) | C36—C37—C38 | 111.32 (14) |
C12—C17—H17A | 109.3 | C36—C37—H37A | 109.4 |
C16—C17—H17A | 109.3 | C38—C37—H37A | 109.4 |
C12—C17—H17B | 109.3 | C36—C37—H37B | 109.4 |
C16—C17—H17B | 109.3 | C38—C37—H37B | 109.4 |
H17A—C17—H17B | 107.9 | H37A—C37—H37B | 108.0 |
O2—C18—N2 | 123.31 (13) | C33—C38—C37 | 110.07 (12) |
O2—C18—C5 | 120.24 (12) | C33—C38—H38A | 109.6 |
N2—C18—C5 | 116.36 (12) | C37—C38—H38A | 109.6 |
N2—C19—C24 | 109.22 (11) | C33—C38—H38B | 109.6 |
N2—C19—C20 | 111.59 (11) | C37—C38—H38B | 109.6 |
C24—C19—C20 | 110.83 (12) | H38A—C38—H38B | 108.2 |
| | | |
C11—C1—C2—C3 | 138.11 (12) | C7—C1—C11—O1 | −34.0 (2) |
C7—C1—C2—C3 | −102.93 (12) | C5—C1—C11—O1 | −168.41 (13) |
C5—C1—C2—C3 | −21.93 (14) | C2—C1—C11—N1 | −140.90 (13) |
C11—C1—C2—C7 | −118.96 (13) | C7—C1—C11—N1 | 146.87 (13) |
C5—C1—C2—C7 | 81.00 (10) | C5—C1—C11—N1 | 12.4 (2) |
C7—C2—C3—C8 | 147.78 (14) | C11—N1—C12—C17 | −105.53 (15) |
C1—C2—C3—C8 | −146.33 (14) | C11—N1—C12—C13 | 131.70 (14) |
C7—C2—C3—C4 | −32.59 (13) | N1—C12—C13—C14 | 175.38 (13) |
C1—C2—C3—C4 | 33.29 (13) | C17—C12—C13—C14 | 53.06 (17) |
C8—C3—C4—C5 | 147.19 (14) | C12—C13—C14—C15 | −54.80 (18) |
C2—C3—C4—C5 | −32.43 (13) | C13—C14—C15—C16 | 56.37 (18) |
C8—C3—C4—C6 | −147.38 (14) | C14—C15—C16—C17 | −56.67 (18) |
C2—C3—C4—C6 | 33.00 (13) | N1—C12—C17—C16 | −174.86 (12) |
C3—C4—C5—C18 | −133.49 (13) | C13—C12—C17—C16 | −53.50 (17) |
C6—C4—C5—C18 | 124.85 (14) | C15—C16—C17—C12 | 55.70 (18) |
C3—C4—C5—C6 | 101.67 (12) | C19—N2—C18—O2 | −4.8 (2) |
C3—C4—C5—C1 | 19.68 (14) | C19—N2—C18—C5 | 171.89 (12) |
C6—C4—C5—C1 | −81.99 (11) | C4—C5—C18—O2 | 117.87 (14) |
C11—C1—C5—C18 | −4.4 (2) | C6—C5—C18—O2 | −166.16 (13) |
C2—C1—C5—C18 | 151.99 (13) | C1—C5—C18—O2 | −28.3 (2) |
C7—C1—C5—C18 | −150.15 (13) | C4—C5—C18—N2 | −58.95 (17) |
C11—C1—C5—C4 | −155.06 (14) | C6—C5—C18—N2 | 17.0 (2) |
C2—C1—C5—C4 | 1.30 (13) | C1—C5—C18—N2 | 154.90 (13) |
C7—C1—C5—C4 | 59.17 (11) | C18—N2—C19—C24 | −134.34 (14) |
C11—C1—C5—C6 | 146.35 (14) | C18—N2—C19—C20 | 102.78 (16) |
C2—C1—C5—C6 | −57.29 (11) | N2—C19—C20—C21 | 175.97 (13) |
C7—C1—C5—C6 | 0.58 (10) | C24—C19—C20—C21 | 54.01 (17) |
C3—C4—C6—C25 | 136.36 (12) | C19—C20—C21—C22 | −53.91 (18) |
C5—C4—C6—C25 | −120.78 (14) | C20—C21—C22—C23 | 54.58 (19) |
C3—C4—C6—C7 | −21.62 (14) | C21—C22—C23—C24 | −55.53 (19) |
C5—C4—C6—C7 | 81.25 (11) | N2—C19—C24—C23 | −179.05 (13) |
C3—C4—C6—C5 | −102.87 (12) | C20—C19—C24—C23 | −55.72 (17) |
C18—C5—C6—C25 | −2.0 (2) | C22—C23—C24—C19 | 56.61 (18) |
C4—C5—C6—C25 | 103.99 (15) | C26—N3—C25—O3 | 0.5 (2) |
C1—C5—C6—C25 | −150.15 (13) | C26—N3—C25—C6 | 178.21 (13) |
C18—C5—C6—C4 | −106.02 (16) | C4—C6—C25—O3 | 42.36 (18) |
C1—C5—C6—C4 | 105.85 (10) | C7—C6—C25—O3 | −167.02 (13) |
C18—C5—C6—C7 | 147.55 (14) | C5—C6—C25—O3 | −30.1 (2) |
C4—C5—C6—C7 | −106.44 (10) | C4—C6—C25—N3 | −135.48 (13) |
C1—C5—C6—C7 | −0.58 (10) | C7—C6—C25—N3 | 15.1 (2) |
C3—C2—C7—C32 | −133.13 (13) | C5—C6—C25—N3 | 152.06 (13) |
C1—C2—C7—C32 | 124.70 (14) | C25—N3—C26—C31 | 114.08 (15) |
C3—C2—C7—C6 | 19.94 (14) | C25—N3—C26—C27 | −124.30 (15) |
C1—C2—C7—C6 | −82.23 (11) | N3—C26—C27—C28 | −67.47 (18) |
C3—C2—C7—C1 | 102.17 (12) | C31—C26—C27—C28 | 54.87 (19) |
C25—C6—C7—C32 | −2.8 (2) | C26—C27—C28—C29 | −54.3 (2) |
C4—C6—C7—C32 | 150.94 (13) | C27—C28—C29—C30 | 54.2 (2) |
C5—C6—C7—C32 | −150.84 (13) | C28—C29—C30—C31 | −55.5 (2) |
C25—C6—C7—C2 | −152.70 (14) | C29—C30—C31—C26 | 57.38 (19) |
C4—C6—C7—C2 | 1.03 (13) | N3—C26—C31—C30 | 65.98 (18) |
C5—C6—C7—C2 | 59.26 (11) | C27—C26—C31—C30 | −56.17 (18) |
C25—C6—C7—C1 | 148.62 (14) | C33—N4—C32—O4 | −6.4 (2) |
C4—C6—C7—C1 | −57.64 (11) | C33—N4—C32—C7 | 169.92 (12) |
C5—C6—C7—C1 | 0.58 (10) | C2—C7—C32—O4 | 117.39 (15) |
C11—C1—C7—C32 | 0.7 (2) | C6—C7—C32—O4 | −28.3 (2) |
C2—C1—C7—C32 | −104.73 (16) | C1—C7—C32—O4 | −167.58 (13) |
C5—C1—C7—C32 | 148.88 (14) | C2—C7—C32—N4 | −59.03 (17) |
C11—C1—C7—C2 | 105.44 (15) | C6—C7—C32—N4 | 155.32 (13) |
C5—C1—C7—C2 | −106.40 (10) | C1—C7—C32—N4 | 16.0 (2) |
C11—C1—C7—C6 | −148.75 (13) | C32—N4—C33—C34 | −153.87 (13) |
C2—C1—C7—C6 | 105.82 (10) | C32—N4—C33—C38 | 82.45 (17) |
C5—C1—C7—C6 | −0.58 (10) | N4—C33—C34—C35 | 178.12 (14) |
C2—C3—C8—C10 | −2.4 (2) | C38—C33—C34—C35 | −56.50 (19) |
C4—C3—C8—C10 | 178.04 (14) | C33—C34—C35—C36 | 53.8 (2) |
C2—C3—C8—C9 | 176.49 (13) | C34—C35—C36—C37 | −52.9 (2) |
C4—C3—C8—C9 | −3.0 (2) | C35—C36—C37—C38 | 54.7 (2) |
C12—N1—C11—O1 | 1.7 (2) | N4—C33—C38—C37 | −179.62 (13) |
C12—N1—C11—C1 | −179.23 (12) | C34—C33—C38—C37 | 57.89 (18) |
C2—C1—C11—O1 | 38.25 (18) | C36—C37—C38—C33 | −57.17 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O2 | 0.900 (18) | 1.824 (18) | 2.7091 (15) | 167.4 (17) |
N2—H02···O3 | 0.895 (18) | 1.907 (19) | 2.7841 (16) | 166.2 (16) |
N3—H03···O4 | 0.927 (17) | 1.804 (17) | 2.7153 (15) | 167.2 (15) |
N4—H04···O1 | 0.953 (19) | 1.81 (2) | 2.7490 (16) | 166.5 (16) |
C4—H4···O3i | 1.00 | 2.39 | 3.3890 (16) | 174 |
C9—H9A···O3i | 0.98 | 2.50 | 3.4717 (18) | 170 |
C14—H14B···O4ii | 0.99 | 2.50 | 3.367 (2) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z. |