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The title compound, C
26H
40N
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 layers by bifurcated (C—H)
2O interactions.
Supporting information
CCDC reference: 217471
Key indicators
- Single-crystal X-ray study
- T = 143 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.104
- Data-to-parameter ratio = 16.5
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 ?
PLAT_320 Alert C Check Hybridisation of C6 in Main Residue ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound was prepared according to Winkler (2002) and recrystallized from a solution in dichloromethane/methanol by evaporation.
H atoms bonded to N atoms were refined freely. Methyl H atoms were located in difference syntheses, idealized (C—H 0.98 Å and H—C—H 109.5°) and refined on the basis of rigid groups allowed to rotate but not tip. H atoms were included using a riding model with fixed C—H bond lengths of 1.00 (methine) or 0.95 Å (aromatic); Uiso(H) values were fixed at 1.2Ueq of the parent atom.
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.
N,
N',
N'',
N'''-3-isopropylidenetetracyclo[3.2.0.0
2,7.0
4,5]heptane- 1,5,6,7-tetracarboxamide
top
Crystal data top
C26H40N4O4 | F(000) = 1024 |
Mr = 472.62 | Dx = 1.174 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3354 (18) Å | Cell parameters from 6314 reflections |
b = 12.1987 (16) Å | θ = 2.2–28.5° |
c = 16.981 (2) Å | µ = 0.08 mm−1 |
β = 104.454 (4)° | T = 143 K |
V = 2674.9 (6) Å3 | Prism, yellow |
Z = 4 | 0.42 × 0.17 × 0.16 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 4203 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.4°, θmin = 1.6° |
Detector resolution: 8.192 pixels mm-1 | h = −16→16 |
ω scans | k = −15→15 |
35207 measured reflections | l = −21→21 |
5478 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6537P] where P = (Fo2 + 2Fc2)/3 |
5478 reflections | (Δ/σ)max < 0.001 |
333 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C26H40N4O4 | V = 2674.9 (6) Å3 |
Mr = 472.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.3354 (18) Å | µ = 0.08 mm−1 |
b = 12.1987 (16) Å | T = 143 K |
c = 16.981 (2) Å | 0.42 × 0.17 × 0.16 mm |
β = 104.454 (4)° | |
Data collection top
Bruker SMART 1000 CCD diffractometer | 4203 reflections with I > 2σ(I) |
35207 measured reflections | Rint = 0.037 |
5478 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.25 e Å−3 |
5478 reflections | Δρmin = −0.19 e Å−3 |
333 parameters | |
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 | 0.40156 (7) | 0.71048 (9) | 0.33737 (6) | 0.0340 (2) | |
O2 | 0.11914 (7) | 0.47992 (8) | 0.25825 (6) | 0.0306 (2) | |
O3 | 0.11756 (7) | 0.43277 (8) | 0.52907 (5) | 0.0283 (2) | |
O4 | 0.40345 (8) | 0.65406 (9) | 0.60557 (6) | 0.0370 (3) | |
N1 | 0.29696 (9) | 0.58874 (10) | 0.25556 (7) | 0.0293 (3) | |
H01 | 0.2397 (13) | 0.5487 (14) | 0.2502 (10) | 0.041 (4)* | |
N2 | 0.06824 (8) | 0.40171 (9) | 0.36231 (7) | 0.0252 (2) | |
H02 | 0.0734 (12) | 0.4042 (13) | 0.4150 (11) | 0.040 (5)* | |
N3 | 0.25291 (9) | 0.51234 (10) | 0.61771 (7) | 0.0305 (3) | |
H03 | 0.3059 (13) | 0.5612 (14) | 0.6196 (10) | 0.043 (5)* | |
N4 | 0.46474 (8) | 0.72064 (10) | 0.50320 (7) | 0.0279 (3) | |
H04 | 0.4506 (13) | 0.7248 (14) | 0.4494 (11) | 0.044 (5)* | |
C1 | 0.25436 (10) | 0.64815 (10) | 0.37850 (8) | 0.0247 (3) | |
C2 | 0.23236 (10) | 0.75299 (10) | 0.41968 (7) | 0.0232 (3) | |
H2 | 0.2698 | 0.8224 | 0.4139 | 0.028* | |
C3 | 0.12181 (10) | 0.75539 (10) | 0.42154 (7) | 0.0222 (3) | |
C4 | 0.10115 (10) | 0.63777 (10) | 0.43070 (7) | 0.0219 (3) | |
H4 | 0.0310 | 0.6123 | 0.4340 | 0.026* | |
C5 | 0.16563 (10) | 0.56943 (11) | 0.38656 (8) | 0.0243 (3) | |
C6 | 0.19863 (10) | 0.58233 (11) | 0.48110 (8) | 0.0246 (3) | |
C7 | 0.28756 (10) | 0.66050 (11) | 0.47355 (8) | 0.0253 (3) | |
C8 | 0.05700 (10) | 0.84005 (11) | 0.41577 (8) | 0.0250 (3) | |
C9 | −0.05506 (11) | 0.82621 (12) | 0.41536 (9) | 0.0306 (3) | |
H9A | −0.0700 | 0.7483 | 0.4206 | 0.037* | |
H9B | −0.0986 | 0.8545 | 0.3642 | 0.037* | |
H9C | −0.0696 | 0.8668 | 0.4611 | 0.037* | |
C10 | 0.09022 (12) | 0.95642 (11) | 0.40749 (9) | 0.0331 (3) | |
H10A | 0.1638 | 0.9578 | 0.4077 | 0.040* | |
H10B | 0.0794 | 1.0000 | 0.4531 | 0.040* | |
H10C | 0.0492 | 0.9873 | 0.3563 | 0.040* | |
C11 | 0.32395 (10) | 0.65085 (11) | 0.32153 (8) | 0.0245 (3) | |
C12 | 0.35941 (11) | 0.57854 (13) | 0.19609 (8) | 0.0340 (3) | |
H12 | 0.4100 | 0.6405 | 0.2041 | 0.041* | |
C13 | 0.28954 (14) | 0.58536 (16) | 0.11088 (9) | 0.0470 (4) | |
H13A | 0.2385 | 0.5259 | 0.1028 | 0.056* | |
H13B | 0.3313 | 0.5785 | 0.0711 | 0.056* | |
H13C | 0.2536 | 0.6561 | 0.1036 | 0.056* | |
C14 | 0.41852 (15) | 0.47190 (18) | 0.20974 (11) | 0.0578 (5) | |
H14A | 0.4632 | 0.4703 | 0.2651 | 0.069* | |
H14B | 0.4611 | 0.4655 | 0.1706 | 0.069* | |
H14C | 0.3696 | 0.4106 | 0.2024 | 0.069* | |
C15 | 0.11694 (9) | 0.47874 (10) | 0.33112 (8) | 0.0231 (3) | |
C16 | 0.01322 (10) | 0.31093 (11) | 0.31338 (8) | 0.0261 (3) | |
H16 | −0.0248 | 0.3405 | 0.2592 | 0.031* | |
C17 | −0.06524 (12) | 0.26435 (13) | 0.35519 (10) | 0.0371 (4) | |
H17A | −0.0294 | 0.2373 | 0.4092 | 0.045* | |
H17B | −0.1026 | 0.2038 | 0.3227 | 0.045* | |
H17C | −0.1144 | 0.3218 | 0.3607 | 0.045* | |
C18 | 0.08837 (12) | 0.22424 (12) | 0.29976 (11) | 0.0393 (4) | |
H18A | 0.1392 | 0.2577 | 0.2742 | 0.047* | |
H18B | 0.0503 | 0.1668 | 0.2641 | 0.047* | |
H18C | 0.1242 | 0.1920 | 0.3521 | 0.047* | |
C19 | 0.18784 (10) | 0.50196 (11) | 0.54487 (8) | 0.0240 (3) | |
C20 | 0.24770 (11) | 0.44230 (13) | 0.68687 (8) | 0.0347 (3) | |
H20 | 0.1742 | 0.4183 | 0.6796 | 0.042* | |
C21 | 0.27845 (15) | 0.51000 (17) | 0.76390 (10) | 0.0526 (5) | |
H21A | 0.3485 | 0.5391 | 0.7699 | 0.063* | |
H21B | 0.2771 | 0.4638 | 0.8109 | 0.063* | |
H21C | 0.2297 | 0.5709 | 0.7607 | 0.063* | |
C22 | 0.31397 (14) | 0.34113 (15) | 0.68934 (11) | 0.0479 (4) | |
H22A | 0.2892 | 0.2993 | 0.6389 | 0.057* | |
H22B | 0.3095 | 0.2955 | 0.7359 | 0.057* | |
H22C | 0.3861 | 0.3630 | 0.6948 | 0.057* | |
C23 | 0.39074 (10) | 0.67671 (11) | 0.53276 (8) | 0.0258 (3) | |
C24 | 0.56923 (10) | 0.73967 (13) | 0.55390 (9) | 0.0333 (3) | |
H24 | 0.5642 | 0.7614 | 0.6096 | 0.040* | |
C25 | 0.61711 (13) | 0.83351 (15) | 0.51756 (11) | 0.0489 (4) | |
H25A | 0.6190 | 0.8149 | 0.4618 | 0.059* | |
H25B | 0.6877 | 0.8465 | 0.5504 | 0.059* | |
H25C | 0.5755 | 0.8999 | 0.5170 | 0.059* | |
C26 | 0.63320 (13) | 0.63621 (16) | 0.56064 (13) | 0.0581 (5) | |
H26A | 0.5998 | 0.5777 | 0.5844 | 0.070* | |
H26B | 0.7026 | 0.6499 | 0.5955 | 0.070* | |
H26C | 0.6387 | 0.6140 | 0.5064 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0344 (5) | 0.0450 (6) | 0.0251 (5) | −0.0151 (5) | 0.0120 (4) | −0.0058 (4) |
O2 | 0.0344 (5) | 0.0320 (5) | 0.0261 (5) | −0.0097 (4) | 0.0088 (4) | −0.0027 (4) |
O3 | 0.0302 (5) | 0.0299 (5) | 0.0257 (5) | −0.0036 (4) | 0.0086 (4) | 0.0055 (4) |
O4 | 0.0338 (5) | 0.0468 (6) | 0.0282 (5) | −0.0094 (5) | 0.0038 (4) | 0.0061 (5) |
N1 | 0.0283 (6) | 0.0334 (7) | 0.0296 (6) | −0.0085 (5) | 0.0134 (5) | −0.0064 (5) |
N2 | 0.0282 (6) | 0.0256 (6) | 0.0220 (6) | −0.0060 (5) | 0.0069 (5) | −0.0036 (5) |
N3 | 0.0297 (6) | 0.0345 (7) | 0.0272 (6) | −0.0055 (5) | 0.0071 (5) | 0.0076 (5) |
N4 | 0.0239 (6) | 0.0356 (7) | 0.0225 (6) | −0.0055 (5) | 0.0024 (5) | −0.0001 (5) |
C1 | 0.0285 (7) | 0.0217 (7) | 0.0261 (7) | −0.0020 (5) | 0.0105 (5) | −0.0008 (5) |
C2 | 0.0288 (7) | 0.0204 (6) | 0.0202 (6) | −0.0028 (5) | 0.0059 (5) | −0.0006 (5) |
C3 | 0.0281 (6) | 0.0217 (7) | 0.0167 (6) | −0.0016 (5) | 0.0054 (5) | −0.0006 (5) |
C4 | 0.0236 (6) | 0.0221 (6) | 0.0204 (6) | 0.0006 (5) | 0.0060 (5) | 0.0008 (5) |
C5 | 0.0235 (6) | 0.0235 (7) | 0.0274 (7) | −0.0008 (5) | 0.0088 (5) | −0.0024 (5) |
C6 | 0.0236 (6) | 0.0253 (7) | 0.0254 (7) | 0.0016 (5) | 0.0073 (5) | 0.0049 (5) |
C7 | 0.0253 (7) | 0.0229 (7) | 0.0271 (7) | −0.0014 (5) | 0.0055 (5) | 0.0031 (5) |
C8 | 0.0338 (7) | 0.0226 (7) | 0.0180 (6) | 0.0024 (5) | 0.0054 (5) | −0.0013 (5) |
C9 | 0.0338 (7) | 0.0275 (7) | 0.0311 (7) | 0.0084 (6) | 0.0094 (6) | 0.0014 (6) |
C10 | 0.0429 (8) | 0.0213 (7) | 0.0333 (8) | 0.0030 (6) | 0.0063 (6) | −0.0013 (6) |
C11 | 0.0271 (7) | 0.0242 (7) | 0.0233 (7) | −0.0006 (5) | 0.0085 (5) | 0.0034 (5) |
C12 | 0.0336 (7) | 0.0427 (9) | 0.0299 (7) | −0.0099 (6) | 0.0157 (6) | −0.0081 (7) |
C13 | 0.0538 (10) | 0.0597 (11) | 0.0305 (8) | 0.0054 (8) | 0.0164 (7) | 0.0060 (8) |
C14 | 0.0526 (10) | 0.0841 (15) | 0.0399 (10) | 0.0276 (10) | 0.0176 (8) | 0.0008 (9) |
C15 | 0.0212 (6) | 0.0220 (7) | 0.0261 (7) | 0.0016 (5) | 0.0062 (5) | −0.0021 (5) |
C16 | 0.0288 (7) | 0.0230 (7) | 0.0253 (7) | −0.0047 (5) | 0.0046 (5) | −0.0012 (5) |
C17 | 0.0357 (8) | 0.0370 (8) | 0.0408 (9) | −0.0128 (6) | 0.0135 (7) | −0.0055 (7) |
C18 | 0.0421 (9) | 0.0256 (8) | 0.0533 (10) | −0.0034 (6) | 0.0178 (7) | −0.0060 (7) |
C19 | 0.0232 (6) | 0.0249 (7) | 0.0261 (7) | 0.0046 (5) | 0.0101 (5) | 0.0042 (5) |
C20 | 0.0334 (7) | 0.0456 (9) | 0.0252 (7) | −0.0046 (7) | 0.0075 (6) | 0.0113 (6) |
C21 | 0.0587 (11) | 0.0705 (13) | 0.0286 (8) | −0.0065 (9) | 0.0110 (8) | 0.0026 (8) |
C22 | 0.0521 (10) | 0.0500 (10) | 0.0423 (9) | 0.0062 (8) | 0.0130 (8) | 0.0203 (8) |
C23 | 0.0268 (7) | 0.0225 (7) | 0.0273 (7) | 0.0002 (5) | 0.0051 (5) | 0.0012 (5) |
C24 | 0.0238 (7) | 0.0445 (9) | 0.0294 (7) | −0.0061 (6) | 0.0025 (6) | −0.0015 (6) |
C25 | 0.0374 (9) | 0.0568 (11) | 0.0493 (10) | −0.0189 (8) | 0.0045 (7) | 0.0029 (8) |
C26 | 0.0333 (9) | 0.0588 (12) | 0.0777 (14) | 0.0079 (8) | 0.0053 (9) | 0.0096 (10) |
Geometric parameters (Å, º) top
O1—C11 | 1.2384 (16) | C10—H10B | 0.9800 |
O2—C15 | 1.2451 (16) | C10—H10C | 0.9800 |
O3—C19 | 1.2398 (16) | C12—C14 | 1.509 (2) |
O4—C23 | 1.2364 (16) | C12—C13 | 1.515 (2) |
N1—C11 | 1.3256 (17) | C12—H12 | 1.0000 |
N1—C12 | 1.4659 (17) | C13—H13A | 0.9800 |
N1—H01 | 0.892 (17) | C13—H13B | 0.9800 |
N2—C15 | 1.3255 (17) | C13—H13C | 0.9800 |
N2—C16 | 1.4666 (17) | C14—H14A | 0.9800 |
N2—H02 | 0.881 (17) | C14—H14B | 0.9800 |
N3—C19 | 1.3278 (17) | C14—H14C | 0.9800 |
N3—C20 | 1.4679 (18) | C16—C18 | 1.514 (2) |
N3—H03 | 0.919 (18) | C16—C17 | 1.5141 (19) |
N4—C23 | 1.3268 (17) | C16—H16 | 1.0000 |
N4—C24 | 1.4622 (17) | C17—H17A | 0.9800 |
N4—H04 | 0.888 (18) | C17—H17B | 0.9800 |
C1—C11 | 1.4988 (18) | C17—H17C | 0.9800 |
C1—C2 | 1.5209 (18) | C18—H18A | 0.9800 |
C1—C5 | 1.5563 (17) | C18—H18B | 0.9800 |
C1—C7 | 1.5707 (18) | C18—H18C | 0.9800 |
C2—C3 | 1.4828 (18) | C20—C22 | 1.512 (2) |
C2—C7 | 1.5217 (18) | C20—C21 | 1.514 (2) |
C2—H2 | 1.0000 | C20—H20 | 1.0000 |
C3—C8 | 1.3345 (18) | C21—H21A | 0.9800 |
C3—C4 | 1.4765 (18) | C21—H21B | 0.9800 |
C4—C5 | 1.5224 (17) | C21—H21C | 0.9800 |
C4—C6 | 1.5245 (17) | C22—H22A | 0.9800 |
C4—H4 | 1.0000 | C22—H22B | 0.9800 |
C5—C15 | 1.4922 (18) | C22—H22C | 0.9800 |
C5—C6 | 1.5630 (18) | C24—C26 | 1.512 (2) |
C6—C19 | 1.4941 (18) | C24—C25 | 1.515 (2) |
C6—C7 | 1.5517 (17) | C24—H24 | 1.0000 |
C7—C23 | 1.5009 (18) | C25—H25A | 0.9800 |
C8—C9 | 1.5021 (19) | C25—H25B | 0.9800 |
C8—C10 | 1.5041 (19) | C25—H25C | 0.9800 |
C9—H9A | 0.9800 | C26—H26A | 0.9800 |
C9—H9B | 0.9800 | C26—H26B | 0.9800 |
C9—H9C | 0.9800 | C26—H26C | 0.9800 |
C10—H10A | 0.9800 | | |
| | | |
C11—N1—C12 | 123.34 (12) | C12—C13—H13A | 109.5 |
C11—N1—H01 | 116.4 (11) | C12—C13—H13B | 109.5 |
C12—N1—H01 | 120.1 (11) | H13A—C13—H13B | 109.5 |
C15—N2—C16 | 122.32 (11) | C12—C13—H13C | 109.5 |
C15—N2—H02 | 117.4 (11) | H13A—C13—H13C | 109.5 |
C16—N2—H02 | 120.2 (11) | H13B—C13—H13C | 109.5 |
C19—N3—C20 | 122.64 (12) | C12—C14—H14A | 109.5 |
C19—N3—H03 | 114.4 (10) | C12—C14—H14B | 109.5 |
C20—N3—H03 | 122.6 (10) | H14A—C14—H14B | 109.5 |
C23—N4—C24 | 122.06 (12) | C12—C14—H14C | 109.5 |
C23—N4—H04 | 115.2 (11) | H14A—C14—H14C | 109.5 |
C24—N4—H04 | 121.6 (11) | H14B—C14—H14C | 109.5 |
C11—C1—C2 | 119.99 (11) | O2—C15—N2 | 122.73 (12) |
C11—C1—C5 | 132.62 (11) | O2—C15—C5 | 120.26 (12) |
C2—C1—C5 | 103.91 (10) | N2—C15—C5 | 116.93 (11) |
C11—C1—C7 | 126.88 (11) | N2—C16—C18 | 110.94 (11) |
C2—C1—C7 | 58.95 (8) | N2—C16—C17 | 108.92 (11) |
C5—C1—C7 | 89.67 (9) | C18—C16—C17 | 111.76 (12) |
C3—C2—C1 | 109.47 (10) | N2—C16—H16 | 108.4 |
C3—C2—C7 | 109.64 (10) | C18—C16—H16 | 108.4 |
C1—C2—C7 | 62.16 (9) | C17—C16—H16 | 108.4 |
C3—C2—H2 | 120.6 | C16—C17—H17A | 109.5 |
C1—C2—H2 | 120.6 | C16—C17—H17B | 109.5 |
C7—C2—H2 | 120.6 | H17A—C17—H17B | 109.5 |
C8—C3—C4 | 128.71 (12) | C16—C17—H17C | 109.5 |
C8—C3—C2 | 130.00 (12) | H17A—C17—H17C | 109.5 |
C4—C3—C2 | 101.29 (10) | H17B—C17—H17C | 109.5 |
C3—C4—C5 | 109.70 (10) | C16—C18—H18A | 109.5 |
C3—C4—C6 | 109.56 (10) | C16—C18—H18B | 109.5 |
C5—C4—C6 | 61.73 (8) | H18A—C18—H18B | 109.5 |
C3—C4—H4 | 120.6 | C16—C18—H18C | 109.5 |
C5—C4—H4 | 120.6 | H18A—C18—H18C | 109.5 |
C6—C4—H4 | 120.6 | H18B—C18—H18C | 109.5 |
C15—C5—C4 | 120.42 (11) | O3—C19—N3 | 123.33 (12) |
C15—C5—C1 | 128.51 (11) | O3—C19—C6 | 119.62 (11) |
C4—C5—C1 | 103.92 (10) | N3—C19—C6 | 116.99 (12) |
C15—C5—C6 | 133.58 (11) | N3—C20—C22 | 110.68 (12) |
C4—C5—C6 | 59.20 (8) | N3—C20—C21 | 108.47 (13) |
C1—C5—C6 | 90.16 (9) | C22—C20—C21 | 113.00 (14) |
C19—C6—C4 | 118.36 (10) | N3—C20—H20 | 108.2 |
C19—C6—C7 | 132.61 (11) | C22—C20—H20 | 108.2 |
C4—C6—C7 | 104.07 (10) | C21—C20—H20 | 108.2 |
C19—C6—C5 | 128.68 (11) | C20—C21—H21A | 109.5 |
C4—C6—C5 | 59.07 (8) | C20—C21—H21B | 109.5 |
C7—C6—C5 | 90.12 (9) | H21A—C21—H21B | 109.5 |
C23—C7—C2 | 122.01 (11) | C20—C21—H21C | 109.5 |
C23—C7—C6 | 128.12 (11) | H21A—C21—H21C | 109.5 |
C2—C7—C6 | 103.91 (10) | H21B—C21—H21C | 109.5 |
C23—C7—C1 | 132.62 (11) | C20—C22—H22A | 109.5 |
C2—C7—C1 | 58.89 (8) | C20—C22—H22B | 109.5 |
C6—C7—C1 | 90.05 (9) | H22A—C22—H22B | 109.5 |
C3—C8—C9 | 122.59 (12) | C20—C22—H22C | 109.5 |
C3—C8—C10 | 122.46 (12) | H22A—C22—H22C | 109.5 |
C9—C8—C10 | 114.93 (12) | H22B—C22—H22C | 109.5 |
C8—C9—H9A | 109.5 | O4—C23—N4 | 122.64 (12) |
C8—C9—H9B | 109.5 | O4—C23—C7 | 120.95 (12) |
H9A—C9—H9B | 109.5 | N4—C23—C7 | 116.35 (12) |
C8—C9—H9C | 109.5 | N4—C24—C26 | 110.42 (13) |
H9A—C9—H9C | 109.5 | N4—C24—C25 | 108.46 (12) |
H9B—C9—H9C | 109.5 | C26—C24—C25 | 111.98 (14) |
C8—C10—H10A | 109.5 | N4—C24—H24 | 108.6 |
C8—C10—H10B | 109.5 | C26—C24—H24 | 108.6 |
H10A—C10—H10B | 109.5 | C25—C24—H24 | 108.6 |
C8—C10—H10C | 109.5 | C24—C25—H25A | 109.5 |
H10A—C10—H10C | 109.5 | C24—C25—H25B | 109.5 |
H10B—C10—H10C | 109.5 | H25A—C25—H25B | 109.5 |
O1—C11—N1 | 123.72 (12) | C24—C25—H25C | 109.5 |
O1—C11—C1 | 119.42 (12) | H25A—C25—H25C | 109.5 |
N1—C11—C1 | 116.85 (11) | H25B—C25—H25C | 109.5 |
N1—C12—C14 | 109.40 (13) | C24—C26—H26A | 109.5 |
N1—C12—C13 | 109.48 (12) | C24—C26—H26B | 109.5 |
C14—C12—C13 | 111.55 (14) | H26A—C26—H26B | 109.5 |
N1—C12—H12 | 108.8 | C24—C26—H26C | 109.5 |
C14—C12—H12 | 108.8 | H26A—C26—H26C | 109.5 |
C13—C12—H12 | 108.8 | H26B—C26—H26C | 109.5 |
| | | |
C11—C1—C2—C3 | 140.03 (12) | C5—C6—C7—C1 | 0.22 (9) |
C5—C1—C2—C3 | −21.47 (13) | C11—C1—C7—C23 | −0.5 (2) |
C7—C1—C2—C3 | −102.50 (11) | C2—C1—C7—C23 | −106.62 (16) |
C11—C1—C2—C7 | −117.47 (13) | C5—C1—C7—C23 | 146.88 (14) |
C5—C1—C2—C7 | 81.03 (10) | C11—C1—C7—C2 | 106.12 (14) |
C1—C2—C3—C8 | −145.96 (13) | C5—C1—C7—C2 | −106.50 (10) |
C7—C2—C3—C8 | 147.60 (13) | C11—C1—C7—C6 | −147.60 (13) |
C1—C2—C3—C4 | 33.44 (13) | C2—C1—C7—C6 | 106.27 (10) |
C7—C2—C3—C4 | −32.99 (13) | C5—C1—C7—C6 | −0.22 (9) |
C8—C3—C4—C5 | 146.38 (13) | C4—C3—C8—C9 | −1.9 (2) |
C2—C3—C4—C5 | −33.03 (13) | C2—C3—C8—C9 | 177.32 (12) |
C8—C3—C4—C6 | −147.62 (13) | C4—C3—C8—C10 | 179.33 (12) |
C2—C3—C4—C6 | 32.97 (13) | C2—C3—C8—C10 | −1.4 (2) |
C3—C4—C5—C15 | −132.31 (12) | C12—N1—C11—O1 | 3.8 (2) |
C6—C4—C5—C15 | 125.49 (13) | C12—N1—C11—C1 | −177.04 (12) |
C3—C4—C5—C1 | 20.49 (13) | C2—C1—C11—O1 | 38.23 (18) |
C6—C4—C5—C1 | −81.70 (10) | C5—C1—C11—O1 | −166.51 (13) |
C3—C4—C5—C6 | 102.19 (11) | C7—C1—C11—O1 | −33.62 (19) |
C11—C1—C5—C15 | −7.7 (2) | C2—C1—C11—N1 | −141.00 (13) |
C2—C1—C5—C15 | 150.40 (12) | C5—C1—C11—N1 | 14.3 (2) |
C7—C1—C5—C15 | −151.80 (13) | C7—C1—C11—N1 | 147.16 (13) |
C11—C1—C5—C4 | −157.44 (13) | C11—N1—C12—C14 | 101.65 (16) |
C2—C1—C5—C4 | 0.63 (13) | C11—N1—C12—C13 | −135.82 (15) |
C7—C1—C5—C4 | 58.43 (11) | C16—N2—C15—O2 | 0.33 (19) |
C11—C1—C5—C6 | 144.35 (14) | C16—N2—C15—C5 | 177.17 (11) |
C2—C1—C5—C6 | −57.58 (11) | C4—C5—C15—O2 | 121.03 (13) |
C7—C1—C5—C6 | 0.22 (9) | C1—C5—C15—O2 | −24.4 (2) |
C3—C4—C6—C19 | 137.28 (12) | C6—C5—C15—O2 | −164.08 (13) |
C5—C4—C6—C19 | −120.30 (13) | C4—C5—C15—N2 | −55.89 (17) |
C3—C4—C6—C7 | −20.92 (13) | C1—C5—C15—N2 | 158.64 (12) |
C5—C4—C6—C7 | 81.51 (10) | C6—C5—C15—N2 | 19.0 (2) |
C3—C4—C6—C5 | −102.42 (11) | C15—N2—C16—C18 | 77.86 (16) |
C15—C5—C6—C19 | −1.0 (2) | C15—N2—C16—C17 | −158.72 (12) |
C4—C5—C6—C19 | 103.28 (14) | C20—N3—C19—O3 | 0.0 (2) |
C1—C5—C6—C19 | −150.55 (13) | C20—N3—C19—C6 | 177.04 (12) |
C15—C5—C6—C4 | −104.27 (15) | C4—C6—C19—O3 | 44.37 (17) |
C1—C5—C6—C4 | 106.17 (10) | C7—C6—C19—O3 | −164.94 (13) |
C15—C5—C6—C7 | 149.33 (14) | C5—C6—C19—O3 | −27.21 (19) |
C4—C5—C6—C7 | −106.39 (10) | C4—C6—C19—N3 | −132.78 (13) |
C1—C5—C6—C7 | −0.22 (9) | C7—C6—C19—N3 | 17.9 (2) |
C3—C2—C7—C23 | −134.03 (12) | C5—C6—C19—N3 | 155.65 (12) |
C1—C2—C7—C23 | 123.74 (14) | C19—N3—C20—C22 | 89.94 (16) |
C3—C2—C7—C6 | 20.76 (13) | C19—N3—C20—C21 | −145.56 (14) |
C1—C2—C7—C6 | −81.46 (10) | C24—N4—C23—O4 | 3.7 (2) |
C3—C2—C7—C1 | 102.22 (11) | C24—N4—C23—C7 | −179.21 (12) |
C19—C6—C7—C23 | −0.9 (2) | C2—C7—C23—O4 | 125.20 (14) |
C4—C6—C7—C23 | 152.71 (13) | C6—C7—C23—O4 | −23.1 (2) |
C5—C6—C7—C23 | −149.25 (13) | C1—C7—C23—O4 | −159.44 (13) |
C19—C6—C7—C2 | −153.60 (13) | C2—C7—C23—N4 | −51.96 (18) |
C4—C6—C7—C2 | 0.04 (13) | C6—C7—C23—N4 | 159.75 (13) |
C5—C6—C7—C2 | 58.08 (11) | C1—C7—C23—N4 | 23.4 (2) |
C19—C6—C7—C1 | 148.55 (14) | C23—N4—C24—C26 | 83.35 (18) |
C4—C6—C7—C1 | −57.81 (11) | C23—N4—C24—C25 | −153.60 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O2 | 0.892 (17) | 1.849 (18) | 2.7279 (15) | 168.3 (16) |
N2—H02···O3 | 0.881 (17) | 1.910 (17) | 2.7686 (15) | 164.3 (15) |
N3—H03···O4 | 0.919 (18) | 1.785 (18) | 2.6959 (16) | 170.6 (15) |
N4—H04···O1 | 0.888 (18) | 1.858 (18) | 2.7331 (16) | 168.1 (16) |
C9—H9B···O2i | 0.98 | 2.54 | 3.4176 (17) | 149 |
C10—H10C···O2i | 0.98 | 2.58 | 3.4461 (18) | 148 |
C4—H4···O3ii | 1.00 | 2.29 | 3.2723 (16) | 167 |
C9—H9A···O3ii | 0.98 | 2.51 | 3.4581 (17) | 164 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C26H40N4O4 |
Mr | 472.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 143 |
a, b, c (Å) | 13.3354 (18), 12.1987 (16), 16.981 (2) |
β (°) | 104.454 (4) |
V (Å3) | 2674.9 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.42 × 0.17 × 0.16 |
|
Data collection |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35207, 5478, 4203 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.104, 1.04 |
No. of reflections | 5478 |
No. of parameters | 333 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.19 |
Selected geometric parameters (Å, º) topC1—C2 | 1.5209 (18) | C3—C8 | 1.3345 (18) |
C1—C5 | 1.5563 (17) | C3—C4 | 1.4765 (18) |
C1—C7 | 1.5707 (18) | C4—C5 | 1.5224 (17) |
C2—C3 | 1.4828 (18) | C4—C6 | 1.5245 (17) |
C2—C7 | 1.5217 (18) | C5—C6 | 1.5630 (18) |
| | | |
C11—C1—C2 | 119.99 (11) | C4—C5—C1 | 103.92 (10) |
C11—C1—C5 | 132.62 (11) | C15—C5—C6 | 133.58 (11) |
C2—C1—C5 | 103.91 (10) | C4—C5—C6 | 59.20 (8) |
C11—C1—C7 | 126.88 (11) | C1—C5—C6 | 90.16 (9) |
C2—C1—C7 | 58.95 (8) | C19—C6—C4 | 118.36 (10) |
C5—C1—C7 | 89.67 (9) | C19—C6—C7 | 132.61 (11) |
C3—C2—C1 | 109.47 (10) | C4—C6—C7 | 104.07 (10) |
C3—C2—C7 | 109.64 (10) | C19—C6—C5 | 128.68 (11) |
C1—C2—C7 | 62.16 (9) | C4—C6—C5 | 59.07 (8) |
C8—C3—C4 | 128.71 (12) | C7—C6—C5 | 90.12 (9) |
C8—C3—C2 | 130.00 (12) | C23—C7—C2 | 122.01 (11) |
C4—C3—C2 | 101.29 (10) | C23—C7—C6 | 128.12 (11) |
C3—C4—C5 | 109.70 (10) | C2—C7—C6 | 103.91 (10) |
C3—C4—C6 | 109.56 (10) | C23—C7—C1 | 132.62 (11) |
C5—C4—C6 | 61.73 (8) | C2—C7—C1 | 58.89 (8) |
C15—C5—C4 | 120.42 (11) | C6—C7—C1 | 90.05 (9) |
C15—C5—C1 | 128.51 (11) | | |
| | | |
C2—C1—C11—O1 | 38.23 (18) | C4—C6—C19—O3 | 44.37 (17) |
C5—C1—C11—O1 | −166.51 (13) | C7—C6—C19—O3 | −164.94 (13) |
C7—C1—C11—O1 | −33.62 (19) | C5—C6—C19—O3 | −27.21 (19) |
C2—C1—C11—N1 | −141.00 (13) | C4—C6—C19—N3 | −132.78 (13) |
C5—C1—C11—N1 | 14.3 (2) | C7—C6—C19—N3 | 17.9 (2) |
C7—C1—C11—N1 | 147.16 (13) | C5—C6—C19—N3 | 155.65 (12) |
C4—C5—C15—O2 | 121.03 (13) | C2—C7—C23—O4 | 125.20 (14) |
C1—C5—C15—O2 | −24.4 (2) | C6—C7—C23—O4 | −23.1 (2) |
C6—C5—C15—O2 | −164.08 (13) | C1—C7—C23—O4 | −159.44 (13) |
C4—C5—C15—N2 | −55.89 (17) | C2—C7—C23—N4 | −51.96 (18) |
C1—C5—C15—N2 | 158.64 (12) | C6—C7—C23—N4 | 159.75 (13) |
C6—C5—C15—N2 | 19.0 (2) | C1—C7—C23—N4 | 23.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O2 | 0.892 (17) | 1.849 (18) | 2.7279 (15) | 168.3 (16) |
N2—H02···O3 | 0.881 (17) | 1.910 (17) | 2.7686 (15) | 164.3 (15) |
N3—H03···O4 | 0.919 (18) | 1.785 (18) | 2.6959 (16) | 170.6 (15) |
N4—H04···O1 | 0.888 (18) | 1.858 (18) | 2.7331 (16) | 168.1 (16) |
C9—H9B···O2i | 0.98 | 2.54 | 3.4176 (17) | 149 |
C10—H10C···O2i | 0.98 | 2.58 | 3.4461 (18) | 148 |
C4—H4···O3ii | 1.00 | 2.29 | 3.2723 (16) | 167 |
C9—H9A···O3ii | 0.98 | 2.51 | 3.4581 (17) | 164 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1. |
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This structure determination forms part of a short series of structures of norbornadiene and quadricyclane tetra-amides. Introductory material was presented in the previous paper (Winkler et al., 2003). Here we present the structure of the title compound, (I), a tetrakis(secondary amide) derivative of quadricyclane.
The molecule (Fig. 1) possesses approximate twofold symmetry. Molecular dimensions, including those of the strained quadricyclane system (Table 1), may be considered normal. The four amide groups are arranged such that four intramolecular hydrogen bonds (Table 2) of the type N—H···O are formed, in the same pattern as reported in the previous paper.
The molecules are connected to form layers perpendicular to the yz plane by two bifurcated intermolecular hydrogen bond systems (C—H)2···O of graph set R21(7) (Fig. 2). One of the H···O interactions, H4···O3, is very short, with a normalized H···O distance of only 2.21 Å.