The title compound, C
30H
26N
2O
4, crystallizes in space group
P2
1/
n, with two crystallographically independent molecules in the asymmetric unit. Two of the phenyl rings are perpendicular to one another. The molecular structure is influenced by strong N—H
O, N—H
N and C—H
O intramolecular interactions, and the crystal structure is stabilized by C—H
O and C—H
π intermolecular interactions.
Supporting information
CCDC reference: 222920
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.056
- wR factor = 0.166
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
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In high-dilution conditions, benzene 1,2-dioxy bis(ethanoyl chloride) (1 mmol) and ortho phenylene diamine (1 mmol) were cyclized in chloroform in the presence of triethylamine, affording the title compound. A single-crystal of (I) suitable for X-ray analysis was obtained by recrystallization from chloroform/methanol (1:1) by slow evaporation.
H atoms were positioned geometrically and were treated as riding on their parent C atoms, with aromatic C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å, ethylene C—H distances of 0.97 Å and N—H distances of 0.86 Å, and with Uiso(H) values of 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms. The methyl groups were allowed to rotate but not to tip.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
30,31-Dimethyl-3,26-dioxa-11,18- diazapentacyclo[26.4.0.0
4,9.0
12,17.0
20,25]dotriconta- 1(32),4,6,8,12,14,16,20,22,24,28,30-dodecaene-10,19-dione
top
Crystal data top
C30H26N2O4 | F(000) = 2016 |
Mr = 478.53 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5463 reflections |
a = 15.5767 (9) Å | θ = 2.3–21.7° |
b = 15.7746 (9) Å | µ = 0.09 mm−1 |
c = 20.5721 (12) Å | T = 293 K |
β = 102.541 (1)° | Block, colourless |
V = 4934.3 (5) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 8 | |
Data collection top
CCD Area Detector diffractometer | 6259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 28.1°, θmin = 1.5° |
ω scans | h = −19→20 |
30895 measured reflections | k = −18→20 |
11480 independent reflections | l = −20→27 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0872P)2 + 0.0307P] where P = (Fo2 + 2Fc2)/3 |
11480 reflections | (Δ/σ)max < 0.001 |
653 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C30H26N2O4 | V = 4934.3 (5) Å3 |
Mr = 478.53 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.5767 (9) Å | µ = 0.09 mm−1 |
b = 15.7746 (9) Å | T = 293 K |
c = 20.5721 (12) Å | 0.24 × 0.20 × 0.16 mm |
β = 102.541 (1)° | |
Data collection top
CCD Area Detector diffractometer | 6259 reflections with I > 2σ(I) |
30895 measured reflections | Rint = 0.031 |
11480 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.30 e Å−3 |
11480 reflections | Δρmin = −0.22 e Å−3 |
653 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 | |
N1A | 1.41506 (10) | 0.26652 (10) | 0.20245 (9) | 0.0563 (4) | |
H1A | 1.3706 | 0.2703 | 0.2208 | 0.068* | |
C2A | 1.49701 (13) | 0.24200 (12) | 0.24294 (11) | 0.0542 (5) | |
C3A | 1.55136 (15) | 0.18642 (13) | 0.21823 (13) | 0.0682 (6) | |
H3A | 1.5329 | 0.1647 | 0.1755 | 0.082* | |
C4A | 1.63108 (17) | 0.16332 (16) | 0.25554 (16) | 0.0816 (8) | |
H4A | 1.6676 | 0.1276 | 0.2378 | 0.098* | |
C5A | 1.65724 (16) | 0.19269 (16) | 0.31909 (16) | 0.0827 (8) | |
H5A | 1.7118 | 0.1771 | 0.3446 | 0.099* | |
C6A | 1.60285 (14) | 0.24586 (15) | 0.34607 (13) | 0.0720 (6) | |
H6A | 1.6201 | 0.2640 | 0.3900 | 0.086* | |
C7A | 1.52261 (12) | 0.27191 (12) | 0.30736 (11) | 0.0549 (5) | |
N8A | 1.46891 (10) | 0.33039 (10) | 0.33343 (9) | 0.0570 (4) | |
H8A | 1.4136 | 0.3196 | 0.3272 | 0.068* | |
C9A | 1.49889 (13) | 0.40151 (14) | 0.36718 (11) | 0.0592 (5) | |
O10A | 1.57672 (11) | 0.41851 (12) | 0.38070 (11) | 0.1051 (7) | |
C11A | 1.43422 (13) | 0.46196 (13) | 0.38580 (10) | 0.0537 (5) | |
C12A | 1.46969 (15) | 0.53779 (15) | 0.41337 (12) | 0.0719 (6) | |
H12A | 1.5301 | 0.5460 | 0.4204 | 0.086* | |
C13A | 1.41855 (17) | 0.60089 (16) | 0.43058 (13) | 0.0815 (7) | |
H13A | 1.4441 | 0.6507 | 0.4498 | 0.098* | |
C14A | 1.32947 (17) | 0.58986 (15) | 0.41915 (13) | 0.0777 (7) | |
H14A | 1.2942 | 0.6332 | 0.4296 | 0.093* | |
C15A | 1.29151 (15) | 0.51564 (13) | 0.39251 (12) | 0.0694 (6) | |
H15A | 1.2309 | 0.5086 | 0.3853 | 0.083* | |
C16A | 1.34357 (13) | 0.45106 (12) | 0.37634 (11) | 0.0556 (5) | |
O17A | 1.30940 (9) | 0.37462 (8) | 0.35071 (8) | 0.0691 (4) | |
C18A | 1.21888 (14) | 0.35825 (14) | 0.35052 (15) | 0.0810 (8) | |
H18A | 1.1814 | 0.3925 | 0.3167 | 0.097* | |
H18B | 1.2068 | 0.3728 | 0.3934 | 0.097* | |
C19A | 1.20025 (13) | 0.26572 (13) | 0.33624 (13) | 0.0603 (6) | |
C20A | 1.20751 (14) | 0.21119 (14) | 0.38939 (12) | 0.0651 (6) | |
H20A | 1.2277 | 0.2326 | 0.4321 | 0.078* | |
C21A | 1.18620 (14) | 0.12599 (14) | 0.38216 (11) | 0.0610 (6) | |
C22A | 1.15514 (14) | 0.09469 (13) | 0.31802 (12) | 0.0607 (6) | |
C23A | 1.14963 (14) | 0.14877 (14) | 0.26506 (11) | 0.0605 (5) | |
H23A | 1.1304 | 0.1272 | 0.2223 | 0.073* | |
C24A | 1.17141 (12) | 0.23407 (13) | 0.27226 (12) | 0.0597 (6) | |
C25A | 1.15893 (14) | 0.28620 (15) | 0.21030 (13) | 0.0751 (7) | |
H25A | 1.1121 | 0.2625 | 0.1763 | 0.090* | |
H25B | 1.1428 | 0.3437 | 0.2194 | 0.090* | |
O26A | 1.24030 (8) | 0.28655 (9) | 0.18736 (8) | 0.0655 (4) | |
C27A | 1.23625 (13) | 0.31209 (12) | 0.12305 (11) | 0.0550 (5) | |
C28A | 1.15879 (15) | 0.33791 (15) | 0.08110 (13) | 0.0757 (7) | |
H28A | 1.1070 | 0.3392 | 0.0967 | 0.091* | |
C29A | 1.15754 (19) | 0.36159 (17) | 0.01695 (14) | 0.0874 (8) | |
H29A | 1.1047 | 0.3773 | −0.0111 | 0.105* | |
C30A | 1.2330 (2) | 0.36229 (18) | −0.00600 (13) | 0.0899 (8) | |
H30A | 1.2323 | 0.3803 | −0.0492 | 0.108* | |
C31A | 1.30961 (17) | 0.33647 (15) | 0.03457 (12) | 0.0732 (7) | |
H31A | 1.3607 | 0.3363 | 0.0181 | 0.088* | |
C32A | 1.31416 (13) | 0.31043 (12) | 0.09975 (10) | 0.0540 (5) | |
C33A | 1.40273 (13) | 0.28413 (13) | 0.13726 (11) | 0.0580 (5) | |
O34A | 1.46308 (10) | 0.28107 (14) | 0.10817 (9) | 0.1012 (6) | |
C35A | 1.1961 (2) | 0.06967 (17) | 0.44247 (13) | 0.0960 (9) | |
H35A | 1.2185 | 0.1023 | 0.4819 | 0.144* | |
H35B | 1.2362 | 0.0245 | 0.4393 | 0.144* | |
H35C | 1.1398 | 0.0464 | 0.4447 | 0.144* | |
C36A | 1.1282 (2) | 0.00294 (15) | 0.30620 (14) | 0.0945 (9) | |
H36A | 1.1005 | −0.0050 | 0.2602 | 0.142* | |
H36B | 1.0876 | −0.0118 | 0.3335 | 0.142* | |
H36C | 1.1793 | −0.0326 | 0.3175 | 0.142* | |
N1B | 0.88809 (10) | 0.40621 (10) | 0.13123 (8) | 0.0505 (4) | |
H1B | 0.8380 | 0.4213 | 0.1385 | 0.061* | |
C2B | 0.95973 (11) | 0.46529 (12) | 0.14452 (10) | 0.0475 (5) | |
C3B | 0.99447 (14) | 0.49495 (14) | 0.09276 (11) | 0.0631 (6) | |
H3B | 0.9699 | 0.4779 | 0.0495 | 0.076* | |
C4B | 1.06496 (16) | 0.54942 (15) | 0.10411 (12) | 0.0720 (7) | |
H4B | 1.0874 | 0.5699 | 0.0688 | 0.086* | |
C5B | 1.10161 (14) | 0.57313 (13) | 0.16786 (13) | 0.0662 (6) | |
H5B | 1.1502 | 0.6089 | 0.1758 | 0.079* | |
C6B | 1.06844 (13) | 0.54542 (13) | 0.22019 (11) | 0.0584 (5) | |
H6B | 1.0942 | 0.5627 | 0.2632 | 0.070* | |
C7B | 0.99572 (12) | 0.49097 (12) | 0.20941 (10) | 0.0468 (5) | |
N8B | 0.95594 (10) | 0.46265 (10) | 0.26080 (8) | 0.0536 (4) | |
H8B | 0.9053 | 0.4390 | 0.2485 | 0.064* | |
C9B | 0.98793 (12) | 0.46823 (12) | 0.32704 (10) | 0.0499 (5) | |
O10B | 1.06118 (10) | 0.49574 (12) | 0.35058 (8) | 0.0830 (5) | |
C11B | 0.93044 (12) | 0.43761 (11) | 0.37200 (9) | 0.0471 (4) | |
C12B | 0.97500 (14) | 0.42029 (13) | 0.43672 (10) | 0.0615 (6) | |
H12B | 1.0355 | 0.4286 | 0.4482 | 0.074* | |
C13B | 0.93258 (18) | 0.39137 (15) | 0.48411 (11) | 0.0748 (7) | |
H13B | 0.9638 | 0.3803 | 0.5272 | 0.090* | |
C14B | 0.84369 (17) | 0.37911 (15) | 0.46705 (12) | 0.0728 (7) | |
H14B | 0.8144 | 0.3591 | 0.4988 | 0.087* | |
C15B | 0.79676 (14) | 0.39594 (14) | 0.40363 (11) | 0.0630 (6) | |
H15B | 0.7363 | 0.3870 | 0.3929 | 0.076* | |
C16B | 0.83928 (12) | 0.42612 (11) | 0.35563 (10) | 0.0482 (5) | |
O17B | 0.79584 (8) | 0.44641 (9) | 0.29236 (7) | 0.0611 (4) | |
C18B | 0.70183 (13) | 0.43428 (16) | 0.27477 (13) | 0.0807 (7) | |
H18C | 0.6773 | 0.4429 | 0.3137 | 0.097* | |
H18D | 0.6888 | 0.3767 | 0.2592 | 0.097* | |
C19B | 0.66083 (12) | 0.49536 (13) | 0.22132 (11) | 0.0553 (5) | |
C20B | 0.64862 (14) | 0.57815 (15) | 0.24098 (11) | 0.0629 (6) | |
H20B | 0.6695 | 0.5930 | 0.2854 | 0.075* | |
C21B | 0.60674 (14) | 0.63908 (13) | 0.19726 (12) | 0.0612 (6) | |
C22B | 0.57653 (13) | 0.61750 (13) | 0.13133 (11) | 0.0561 (5) | |
C23B | 0.58890 (13) | 0.53525 (14) | 0.11191 (11) | 0.0579 (5) | |
H23B | 0.5688 | 0.5209 | 0.0674 | 0.069* | |
C24B | 0.62958 (12) | 0.47352 (12) | 0.15534 (11) | 0.0529 (5) | |
C25B | 0.63240 (13) | 0.38470 (13) | 0.13043 (13) | 0.0712 (7) | |
H25C | 0.6151 | 0.3454 | 0.1615 | 0.085* | |
H25D | 0.5917 | 0.3787 | 0.0877 | 0.085* | |
O26B | 0.72018 (8) | 0.36591 (8) | 0.12353 (8) | 0.0620 (4) | |
C27B | 0.73532 (12) | 0.28645 (12) | 0.10082 (10) | 0.0490 (5) | |
C28B | 0.67016 (14) | 0.22507 (13) | 0.08635 (11) | 0.0632 (6) | |
H28B | 0.6133 | 0.2373 | 0.0908 | 0.076* | |
C29B | 0.69013 (15) | 0.14582 (14) | 0.06528 (11) | 0.0683 (6) | |
H29B | 0.6468 | 0.1042 | 0.0568 | 0.082* | |
C30B | 0.77274 (16) | 0.12772 (14) | 0.05678 (12) | 0.0737 (7) | |
H30B | 0.7857 | 0.0745 | 0.0421 | 0.088* | |
C31B | 0.83654 (15) | 0.18956 (13) | 0.07031 (12) | 0.0688 (6) | |
H31B | 0.8926 | 0.1773 | 0.0641 | 0.083* | |
C32B | 0.81995 (12) | 0.26955 (12) | 0.09296 (10) | 0.0508 (5) | |
C33B | 0.89683 (13) | 0.32842 (13) | 0.10781 (12) | 0.0621 (6) | |
O34B | 0.96723 (11) | 0.30439 (11) | 0.09933 (15) | 0.1351 (10) | |
C35B | 0.5943 (2) | 0.72788 (15) | 0.22187 (16) | 0.1033 (10) | |
H35D | 0.6144 | 0.7299 | 0.2694 | 0.155* | |
H35E | 0.5331 | 0.7427 | 0.2102 | 0.155* | |
H35F | 0.6275 | 0.7673 | 0.2016 | 0.155* | |
C36B | 0.52947 (17) | 0.68101 (17) | 0.08125 (13) | 0.0884 (8) | |
H36D | 0.5096 | 0.6536 | 0.0390 | 0.133* | |
H36E | 0.5690 | 0.7262 | 0.0767 | 0.133* | |
H36F | 0.4799 | 0.7036 | 0.0962 | 0.133* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0443 (9) | 0.0631 (11) | 0.0662 (12) | 0.0092 (8) | 0.0223 (8) | 0.0008 (9) |
C2A | 0.0427 (11) | 0.0493 (12) | 0.0750 (15) | 0.0038 (9) | 0.0225 (10) | 0.0068 (11) |
C3A | 0.0622 (14) | 0.0558 (13) | 0.0956 (17) | 0.0138 (11) | 0.0365 (13) | 0.0066 (12) |
C4A | 0.0652 (16) | 0.0695 (16) | 0.121 (2) | 0.0260 (13) | 0.0443 (16) | 0.0229 (16) |
C5A | 0.0488 (14) | 0.0816 (18) | 0.119 (2) | 0.0239 (12) | 0.0214 (15) | 0.0359 (17) |
C6A | 0.0513 (13) | 0.0757 (16) | 0.0872 (17) | 0.0092 (11) | 0.0112 (12) | 0.0212 (13) |
C7A | 0.0392 (11) | 0.0502 (11) | 0.0780 (15) | 0.0052 (9) | 0.0183 (10) | 0.0126 (11) |
N8A | 0.0365 (9) | 0.0571 (10) | 0.0771 (12) | −0.0004 (7) | 0.0119 (8) | −0.0037 (9) |
C9A | 0.0417 (12) | 0.0742 (14) | 0.0642 (13) | −0.0079 (10) | 0.0173 (10) | −0.0047 (11) |
O10A | 0.0477 (10) | 0.1178 (15) | 0.1543 (18) | −0.0185 (9) | 0.0318 (11) | −0.0527 (13) |
C11A | 0.0489 (12) | 0.0578 (12) | 0.0566 (12) | −0.0074 (9) | 0.0161 (9) | −0.0001 (10) |
C12A | 0.0594 (14) | 0.0723 (16) | 0.0857 (17) | −0.0161 (12) | 0.0197 (12) | −0.0149 (13) |
C13A | 0.0814 (18) | 0.0646 (15) | 0.103 (2) | −0.0197 (13) | 0.0302 (15) | −0.0248 (14) |
C14A | 0.0825 (18) | 0.0551 (14) | 0.106 (2) | −0.0027 (12) | 0.0435 (15) | −0.0084 (13) |
C15A | 0.0578 (13) | 0.0544 (13) | 0.1035 (19) | −0.0026 (10) | 0.0342 (13) | −0.0023 (12) |
C16A | 0.0505 (12) | 0.0493 (12) | 0.0711 (14) | −0.0048 (9) | 0.0222 (10) | 0.0004 (10) |
O17A | 0.0430 (8) | 0.0535 (9) | 0.1170 (13) | −0.0083 (6) | 0.0310 (8) | −0.0137 (8) |
C18A | 0.0462 (13) | 0.0594 (14) | 0.145 (2) | −0.0071 (10) | 0.0374 (14) | −0.0100 (14) |
C19A | 0.0394 (11) | 0.0535 (13) | 0.0945 (18) | −0.0049 (9) | 0.0289 (11) | −0.0040 (12) |
C20A | 0.0548 (13) | 0.0679 (15) | 0.0768 (16) | −0.0085 (11) | 0.0237 (11) | −0.0154 (12) |
C21A | 0.0607 (13) | 0.0609 (14) | 0.0674 (15) | 0.0000 (10) | 0.0271 (11) | −0.0004 (11) |
C22A | 0.0628 (14) | 0.0529 (12) | 0.0721 (15) | −0.0021 (10) | 0.0272 (11) | −0.0048 (11) |
C23A | 0.0560 (13) | 0.0664 (14) | 0.0627 (14) | −0.0003 (10) | 0.0208 (10) | −0.0009 (11) |
C24A | 0.0369 (11) | 0.0592 (13) | 0.0891 (17) | 0.0034 (9) | 0.0269 (11) | 0.0104 (12) |
C25A | 0.0494 (13) | 0.0790 (16) | 0.1055 (19) | 0.0147 (11) | 0.0359 (13) | 0.0319 (14) |
O26A | 0.0419 (8) | 0.0758 (10) | 0.0832 (11) | 0.0064 (7) | 0.0230 (7) | 0.0221 (8) |
C27A | 0.0496 (12) | 0.0446 (11) | 0.0723 (14) | −0.0010 (9) | 0.0168 (10) | 0.0078 (10) |
C28A | 0.0520 (14) | 0.0741 (16) | 0.100 (2) | 0.0104 (11) | 0.0149 (13) | 0.0258 (14) |
C29A | 0.0741 (19) | 0.0882 (18) | 0.090 (2) | 0.0060 (14) | −0.0033 (15) | 0.0157 (16) |
C30A | 0.096 (2) | 0.107 (2) | 0.0629 (16) | 0.0003 (17) | 0.0076 (15) | −0.0001 (15) |
C31A | 0.0741 (17) | 0.0861 (17) | 0.0627 (15) | −0.0037 (13) | 0.0221 (13) | −0.0130 (13) |
C32A | 0.0508 (12) | 0.0508 (11) | 0.0622 (14) | −0.0061 (9) | 0.0164 (10) | −0.0099 (10) |
C33A | 0.0435 (11) | 0.0645 (13) | 0.0703 (15) | −0.0076 (9) | 0.0220 (10) | −0.0118 (11) |
O34A | 0.0494 (10) | 0.1789 (19) | 0.0812 (12) | 0.0041 (11) | 0.0271 (9) | 0.0058 (12) |
C35A | 0.123 (3) | 0.093 (2) | 0.0774 (18) | −0.0022 (17) | 0.0316 (17) | 0.0133 (16) |
C36A | 0.132 (3) | 0.0547 (15) | 0.101 (2) | −0.0114 (15) | 0.0346 (18) | −0.0093 (14) |
N1B | 0.0390 (9) | 0.0563 (10) | 0.0585 (10) | −0.0017 (7) | 0.0160 (7) | −0.0051 (8) |
C2B | 0.0367 (10) | 0.0502 (11) | 0.0580 (12) | −0.0002 (8) | 0.0155 (9) | 0.0008 (9) |
C3B | 0.0653 (14) | 0.0712 (14) | 0.0576 (13) | −0.0074 (11) | 0.0241 (11) | 0.0002 (11) |
C4B | 0.0747 (16) | 0.0763 (16) | 0.0765 (17) | −0.0141 (13) | 0.0412 (13) | 0.0042 (13) |
C5B | 0.0533 (13) | 0.0632 (14) | 0.0890 (18) | −0.0152 (10) | 0.0309 (12) | −0.0008 (12) |
C6B | 0.0482 (12) | 0.0635 (13) | 0.0663 (14) | −0.0104 (10) | 0.0184 (10) | −0.0027 (11) |
C7B | 0.0393 (10) | 0.0485 (11) | 0.0559 (12) | −0.0021 (8) | 0.0173 (9) | 0.0025 (9) |
N8B | 0.0461 (9) | 0.0642 (10) | 0.0518 (10) | −0.0174 (8) | 0.0133 (8) | −0.0002 (8) |
C9B | 0.0387 (11) | 0.0546 (11) | 0.0558 (13) | 0.0003 (9) | 0.0086 (9) | 0.0014 (10) |
O10B | 0.0442 (9) | 0.1323 (15) | 0.0684 (10) | −0.0206 (9) | 0.0032 (7) | 0.0109 (10) |
C11B | 0.0509 (11) | 0.0417 (10) | 0.0490 (12) | −0.0006 (8) | 0.0119 (9) | −0.0007 (9) |
C12B | 0.0611 (14) | 0.0678 (14) | 0.0533 (13) | −0.0074 (11) | 0.0071 (10) | −0.0017 (11) |
C13B | 0.0875 (19) | 0.0886 (17) | 0.0458 (13) | −0.0125 (14) | 0.0089 (12) | 0.0045 (12) |
C14B | 0.0871 (18) | 0.0809 (16) | 0.0587 (15) | −0.0070 (13) | 0.0343 (13) | 0.0082 (12) |
C15B | 0.0562 (13) | 0.0712 (14) | 0.0666 (15) | −0.0014 (11) | 0.0247 (11) | 0.0108 (11) |
C16B | 0.0477 (11) | 0.0466 (11) | 0.0521 (12) | 0.0026 (8) | 0.0145 (9) | 0.0041 (9) |
O17B | 0.0356 (7) | 0.0847 (10) | 0.0632 (9) | 0.0008 (6) | 0.0112 (6) | 0.0241 (8) |
C18B | 0.0411 (12) | 0.0984 (18) | 0.1003 (19) | −0.0049 (12) | 0.0103 (12) | 0.0401 (15) |
C19B | 0.0335 (10) | 0.0616 (13) | 0.0722 (15) | 0.0013 (9) | 0.0148 (10) | 0.0169 (11) |
C20B | 0.0535 (13) | 0.0773 (16) | 0.0590 (13) | −0.0089 (11) | 0.0147 (10) | −0.0020 (12) |
C21B | 0.0548 (13) | 0.0577 (13) | 0.0754 (16) | 0.0006 (10) | 0.0239 (11) | 0.0006 (12) |
C22B | 0.0434 (11) | 0.0581 (13) | 0.0708 (15) | 0.0054 (9) | 0.0210 (10) | 0.0116 (11) |
C23B | 0.0450 (11) | 0.0729 (15) | 0.0570 (13) | 0.0023 (10) | 0.0138 (9) | −0.0028 (11) |
C24B | 0.0328 (10) | 0.0537 (12) | 0.0753 (15) | 0.0016 (8) | 0.0185 (10) | −0.0010 (11) |
C25B | 0.0405 (12) | 0.0618 (14) | 0.116 (2) | 0.0016 (10) | 0.0268 (12) | −0.0124 (13) |
O26B | 0.0394 (8) | 0.0512 (8) | 0.1001 (11) | −0.0010 (6) | 0.0255 (7) | −0.0127 (8) |
C27B | 0.0417 (10) | 0.0474 (11) | 0.0575 (12) | 0.0026 (8) | 0.0102 (9) | 0.0008 (9) |
C28B | 0.0472 (12) | 0.0588 (13) | 0.0845 (16) | −0.0041 (10) | 0.0166 (11) | −0.0073 (11) |
C29B | 0.0620 (15) | 0.0581 (14) | 0.0822 (16) | −0.0113 (11) | 0.0097 (12) | −0.0074 (12) |
C30B | 0.0699 (16) | 0.0510 (13) | 0.0987 (18) | 0.0043 (11) | 0.0150 (13) | −0.0148 (12) |
C31B | 0.0525 (13) | 0.0562 (13) | 0.0996 (18) | 0.0078 (10) | 0.0209 (12) | −0.0087 (12) |
C32B | 0.0418 (11) | 0.0494 (11) | 0.0605 (12) | 0.0037 (8) | 0.0098 (9) | 0.0006 (9) |
C33B | 0.0384 (11) | 0.0563 (13) | 0.0929 (16) | 0.0031 (9) | 0.0172 (10) | −0.0056 (12) |
O34B | 0.0498 (11) | 0.0799 (12) | 0.286 (3) | −0.0069 (9) | 0.0598 (15) | −0.0536 (15) |
C35B | 0.126 (3) | 0.0609 (16) | 0.130 (3) | 0.0005 (16) | 0.043 (2) | −0.0191 (16) |
C36B | 0.0767 (18) | 0.0877 (18) | 0.104 (2) | 0.0227 (14) | 0.0268 (15) | 0.0353 (16) |
Geometric parameters (Å, º) top
N1A—C33A | 1.342 (3) | N1B—C33B | 1.336 (2) |
N1A—C2A | 1.418 (2) | N1B—C2B | 1.434 (2) |
N1A—H1A | 0.8600 | N1B—H1B | 0.8600 |
C2A—C7A | 1.381 (3) | C2B—C3B | 1.377 (3) |
C2A—C3A | 1.389 (3) | C2B—C7B | 1.391 (3) |
C3A—C4A | 1.360 (3) | C3B—C4B | 1.374 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.363 (4) | C4B—C5B | 1.364 (3) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.390 (3) | C5B—C6B | 1.363 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—C7A | 1.390 (3) | C6B—C7B | 1.400 (3) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—N8A | 1.426 (2) | C7B—N8B | 1.409 (2) |
N8A—C9A | 1.348 (3) | N8B—C9B | 1.348 (2) |
N8A—H8A | 0.8600 | N8B—H8B | 0.8600 |
C9A—O10A | 1.213 (2) | C9B—O10B | 1.218 (2) |
C9A—C11A | 1.496 (3) | C9B—C11B | 1.500 (3) |
C11A—C12A | 1.386 (3) | C11B—C12B | 1.388 (3) |
C11A—C16A | 1.394 (3) | C11B—C16B | 1.398 (3) |
C12A—C13A | 1.368 (3) | C12B—C13B | 1.369 (3) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.367 (3) | C13B—C14B | 1.366 (3) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.371 (3) | C14B—C15B | 1.376 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.387 (3) | C15B—C16B | 1.387 (3) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—O17A | 1.376 (2) | C16B—O17B | 1.368 (2) |
O17A—C18A | 1.433 (2) | O17B—C18B | 1.443 (2) |
C18A—C19A | 1.505 (3) | C18B—C19B | 1.497 (3) |
C18A—H18A | 0.9700 | C18B—H18C | 0.9700 |
C18A—H18B | 0.9700 | C18B—H18D | 0.9700 |
C19A—C20A | 1.376 (3) | C19B—C24B | 1.382 (3) |
C19A—C24A | 1.388 (3) | C19B—C20B | 1.392 (3) |
C20A—C21A | 1.385 (3) | C20B—C21B | 1.380 (3) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.393 (3) | C21B—C22B | 1.378 (3) |
C21A—C35A | 1.506 (3) | C21B—C35B | 1.516 (3) |
C22A—C23A | 1.372 (3) | C22B—C23B | 1.383 (3) |
C22A—C36A | 1.512 (3) | C22B—C36B | 1.508 (3) |
C23A—C24A | 1.388 (3) | C23B—C24B | 1.379 (3) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—C25A | 1.494 (3) | C24B—C25B | 1.496 (3) |
C25A—O26A | 1.445 (2) | C25B—O26B | 1.436 (2) |
C25A—H25A | 0.9700 | C25B—H25C | 0.9700 |
C25A—H25B | 0.9700 | C25B—H25D | 0.9700 |
O26A—C27A | 1.371 (2) | O26B—C27B | 1.376 (2) |
C27A—C28A | 1.384 (3) | C27B—C28B | 1.387 (3) |
C27A—C32A | 1.398 (3) | C27B—C32B | 1.388 (2) |
C28A—C29A | 1.368 (3) | C28B—C29B | 1.381 (3) |
C28A—H28A | 0.9300 | C28B—H28B | 0.9300 |
C29A—C30A | 1.358 (4) | C29B—C30B | 1.366 (3) |
C29A—H29A | 0.9300 | C29B—H29B | 0.9300 |
C30A—C31A | 1.362 (4) | C30B—C31B | 1.377 (3) |
C30A—H30A | 0.9300 | C30B—H30B | 0.9300 |
C31A—C32A | 1.389 (3) | C31B—C32B | 1.389 (3) |
C31A—H31A | 0.9300 | C31B—H31B | 0.9300 |
C32A—C33A | 1.486 (3) | C32B—C33B | 1.494 (3) |
C33A—O34A | 1.220 (2) | C33B—O34B | 1.208 (2) |
C35A—H35A | 0.9600 | C35B—H35D | 0.9600 |
C35A—H35B | 0.9600 | C35B—H35E | 0.9600 |
C35A—H35C | 0.9600 | C35B—H35F | 0.9600 |
C36A—H36A | 0.9600 | C36B—H36D | 0.9600 |
C36A—H36B | 0.9600 | C36B—H36E | 0.9600 |
C36A—H36C | 0.9600 | C36B—H36F | 0.9600 |
| | | |
C33A—N1A—C2A | 123.96 (16) | C33B—N1B—C2B | 121.99 (15) |
C33A—N1A—H1A | 118.0 | C33B—N1B—H1B | 119.0 |
C2A—N1A—H1A | 118.0 | C2B—N1B—H1B | 119.0 |
C7A—C2A—C3A | 119.6 (2) | C3B—C2B—C7B | 119.9 (2) |
C7A—C2A—N1A | 120.4 (2) | C3B—C2B—N1B | 119.6 (2) |
C3A—C2A—N1A | 120.0 (2) | C7B—C2B—N1B | 120.5 (2) |
C4A—C3A—C2A | 121.1 (2) | C4B—C3B—C2B | 121.0 (2) |
C4A—C3A—H3A | 119.4 | C4B—C3B—H3B | 119.5 |
C2A—C3A—H3A | 119.4 | C2B—C3B—H3B | 119.5 |
C5A—C4A—C3A | 119.8 (2) | C5B—C4B—C3B | 119.2 (2) |
C5A—C4A—H4A | 120.1 | C5B—C4B—H4B | 120.4 |
C3A—C4A—H4A | 120.1 | C3B—C4B—H4B | 120.4 |
C4A—C5A—C6A | 120.4 (2) | C4B—C5B—C6B | 121.3 (2) |
C4A—C5A—H5A | 119.8 | C4B—C5B—H5B | 119.3 |
C6A—C5A—H5A | 119.8 | C6B—C5B—H5B | 119.3 |
C5A—C6A—C7A | 120.0 (2) | C5B—C6B—C7B | 120.3 (2) |
C5A—C6A—H6A | 120.0 | C5B—C6B—H6B | 119.9 |
C7A—C6A—H6A | 120.0 | C7B—C6B—H6B | 119.9 |
C2A—C7A—C6A | 119.00 (19) | C2B—C7B—C6B | 118.3 (2) |
C2A—C7A—N8A | 120.7 (2) | C2B—C7B—N8B | 118.4 (2) |
C6A—C7A—N8A | 120.2 (2) | C6B—C7B—N8B | 123.2 (2) |
C9A—N8A—C7A | 124.48 (17) | C9B—N8B—C7B | 127.67 (16) |
C9A—N8A—H8A | 117.8 | C9B—N8B—H8B | 116.2 |
C7A—N8A—H8A | 117.8 | C7B—N8B—H8B | 116.2 |
O10A—C9A—N8A | 121.26 (19) | O10B—C9B—N8B | 122.25 (18) |
O10A—C9A—C11A | 119.7 (2) | O10B—C9B—C11B | 120.16 (18) |
N8A—C9A—C11A | 119.02 (17) | N8B—C9B—C11B | 117.58 (17) |
C12A—C11A—C16A | 117.73 (19) | C12B—C11B—C16B | 118.40 (18) |
C12A—C11A—C9A | 115.1 (2) | C12B—C11B—C9B | 114.4 (2) |
C16A—C11A—C9A | 127.1 (2) | C16B—C11B—C9B | 127.2 (2) |
C13A—C12A—C11A | 122.1 (2) | C13B—C12B—C11B | 122.0 (2) |
C13A—C12A—H12A | 119.0 | C13B—C12B—H12B | 119.0 |
C11A—C12A—H12A | 119.0 | C11B—C12B—H12B | 119.0 |
C12A—C13A—C14A | 119.3 (2) | C14B—C13B—C12B | 118.9 (2) |
C12A—C13A—H13A | 120.4 | C14B—C13B—H13B | 120.6 |
C14A—C13A—H13A | 120.4 | C12B—C13B—H13B | 120.6 |
C15A—C14A—C13A | 120.7 (2) | C13B—C14B—C15B | 121.1 (2) |
C15A—C14A—H14A | 119.6 | C13B—C14B—H14B | 119.5 |
C13A—C14A—H14A | 119.6 | C15B—C14B—H14B | 119.5 |
C14A—C15A—C16A | 119.9 (2) | C14B—C15B—C16B | 120.3 (2) |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 119.9 |
C16A—C15A—H15A | 120.0 | C16B—C15B—H15B | 119.9 |
O17A—C16A—C15A | 122.5 (2) | O17B—C16B—C15B | 122.9 (2) |
O17A—C16A—C11A | 117.2 (2) | O17B—C16B—C11B | 117.8 (2) |
C15A—C16A—C11A | 120.23 (19) | C15B—C16B—C11B | 119.33 (18) |
C16A—O17A—C18A | 117.2 (2) | C16B—O17B—C18B | 118.2 (2) |
O17A—C18A—C19A | 108.87 (16) | O17B—C18B—C19B | 110.29 (16) |
O17A—C18A—H18A | 109.9 | O17B—C18B—H18C | 109.6 |
C19A—C18A—H18A | 109.9 | C19B—C18B—H18C | 109.6 |
O17A—C18A—H18B | 109.9 | O17B—C18B—H18D | 109.6 |
C19A—C18A—H18B | 109.9 | C19B—C18B—H18D | 109.6 |
H18A—C18A—H18B | 108.3 | H18C—C18B—H18D | 108.1 |
C20A—C19A—C24A | 118.84 (19) | C24B—C19B—C20B | 118.53 (19) |
C20A—C19A—C18A | 118.2 (2) | C24B—C19B—C18B | 124.3 (2) |
C24A—C19A—C18A | 122.9 (2) | C20B—C19B—C18B | 117.0 (2) |
C19A—C20A—C21A | 123.0 (2) | C21B—C20B—C19B | 122.6 (2) |
C19A—C20A—H20A | 118.5 | C21B—C20B—H20B | 118.7 |
C21A—C20A—H20A | 118.5 | C19B—C20B—H20B | 118.7 |
C20A—C21A—C22A | 118.1 (2) | C20B—C21B—C22B | 118.8 (2) |
C20A—C21A—C35A | 120.3 (2) | C20B—C21B—C35B | 120.2 (2) |
C22A—C21A—C35A | 121.5 (2) | C22B—C21B—C35B | 121.0 (2) |
C23A—C22A—C21A | 118.7 (2) | C21B—C22B—C23B | 118.5 (2) |
C23A—C22A—C36A | 120.0 (2) | C21B—C22B—C36B | 121.3 (2) |
C21A—C22A—C36A | 121.2 (2) | C23B—C22B—C36B | 120.2 (2) |
C22A—C23A—C24A | 123.1 (2) | C24B—C23B—C22B | 123.3 (2) |
C22A—C23A—H23A | 118.4 | C24B—C23B—H23B | 118.4 |
C24A—C23A—H23A | 118.4 | C22B—C23B—H23B | 118.4 |
C23A—C24A—C19A | 118.1 (2) | C23B—C24B—C19B | 118.32 (19) |
C23A—C24A—C25A | 117.3 (2) | C23B—C24B—C25B | 118.9 (2) |
C19A—C24A—C25A | 124.5 (2) | C19B—C24B—C25B | 122.6 (2) |
O26A—C25A—C24A | 108.66 (16) | O26B—C25B—C24B | 109.06 (16) |
O26A—C25A—H25A | 110.0 | O26B—C25B—H25C | 109.9 |
C24A—C25A—H25A | 110.0 | C24B—C25B—H25C | 109.9 |
O26A—C25A—H25B | 110.0 | O26B—C25B—H25D | 109.9 |
C24A—C25A—H25B | 110.0 | C24B—C25B—H25D | 109.9 |
H25A—C25A—H25B | 108.3 | H25C—C25B—H25D | 108.3 |
C27A—O26A—C25A | 117.2 (2) | C27B—O26B—C25B | 117.3 (1) |
O26A—C27A—C28A | 122.7 (2) | O26B—C27B—C28B | 122.5 (2) |
O26A—C27A—C32A | 117.6 (2) | O26B—C27B—C32B | 116.8 (2) |
C28A—C27A—C32A | 119.7 (2) | C28B—C27B—C32B | 120.65 (18) |
C29A—C28A—C27A | 120.7 (2) | C29B—C28B—C27B | 119.7 (2) |
C29A—C28A—H28A | 119.7 | C29B—C28B—H28B | 120.2 |
C27A—C28A—H28A | 119.7 | C27B—C28B—H28B | 120.2 |
C30A—C29A—C28A | 120.4 (3) | C30B—C29B—C28B | 120.8 (2) |
C30A—C29A—H29A | 119.8 | C30B—C29B—H29B | 119.6 |
C28A—C29A—H29A | 119.8 | C28B—C29B—H29B | 119.6 |
C29A—C30A—C31A | 119.6 (3) | C29B—C30B—C31B | 119.0 (2) |
C29A—C30A—H30A | 120.2 | C29B—C30B—H30B | 120.5 |
C31A—C30A—H30A | 120.2 | C31B—C30B—H30B | 120.5 |
C30A—C31A—C32A | 122.3 (2) | C30B—C31B—C32B | 122.2 (2) |
C30A—C31A—H31A | 118.9 | C30B—C31B—H31B | 118.9 |
C32A—C31A—H31A | 118.9 | C32B—C31B—H31B | 118.9 |
C31A—C32A—C27A | 117.3 (2) | C27B—C32B—C31B | 117.66 (18) |
C31A—C32A—C33A | 115.5 (2) | C27B—C32B—C33B | 126.6 (2) |
C27A—C32A—C33A | 127.2 (2) | C31B—C32B—C33B | 115.7 (2) |
O34A—C33A—N1A | 121.6 (2) | O34B—C33B—N1B | 120.46 (19) |
O34A—C33A—C32A | 118.9 (2) | O34B—C33B—C32B | 119.20 (19) |
N1A—C33A—C32A | 119.47 (16) | N1B—C33B—C32B | 120.33 (16) |
C21A—C35A—H35A | 109.5 | C21B—C35B—H35D | 109.5 |
C21A—C35A—H35B | 109.5 | C21B—C35B—H35E | 109.5 |
H35A—C35A—H35B | 109.5 | H35D—C35B—H35E | 109.5 |
C21A—C35A—H35C | 109.5 | C21B—C35B—H35F | 109.5 |
H35A—C35A—H35C | 109.5 | H35D—C35B—H35F | 109.5 |
H35B—C35A—H35C | 109.5 | H35E—C35B—H35F | 109.5 |
C22A—C36A—H36A | 109.5 | C22B—C36B—H36D | 109.5 |
C22A—C36A—H36B | 109.5 | C22B—C36B—H36E | 109.5 |
H36A—C36A—H36B | 109.5 | H36D—C36B—H36E | 109.5 |
C22A—C36A—H36C | 109.5 | C22B—C36B—H36F | 109.5 |
H36A—C36A—H36C | 109.5 | H36D—C36B—H36F | 109.5 |
H36B—C36A—H36C | 109.5 | H36E—C36B—H36F | 109.5 |
| | | |
C33A—N1A—C2A—C7A | 140.8 (2) | C33B—N1B—C2B—C3B | 64.6 (3) |
C33A—N1A—C2A—C3A | −40.3 (3) | C33B—N1B—C2B—C7B | −113.7 (2) |
C7A—C2A—C3A—C4A | −2.5 (3) | C7B—C2B—C3B—C4B | 0.4 (3) |
N1A—C2A—C3A—C4A | 178.60 (19) | N1B—C2B—C3B—C4B | −177.8 (2) |
C2A—C3A—C4A—C5A | 2.2 (4) | C2B—C3B—C4B—C5B | 1.0 (4) |
C3A—C4A—C5A—C6A | 0.2 (4) | C3B—C4B—C5B—C6B | −1.5 (4) |
C4A—C5A—C6A—C7A | −2.4 (4) | C4B—C5B—C6B—C7B | 0.5 (3) |
C3A—C2A—C7A—C6A | 0.3 (3) | C3B—C2B—C7B—C6B | −1.5 (3) |
N1A—C2A—C7A—C6A | 179.21 (18) | N1B—C2B—C7B—C6B | 176.82 (17) |
C3A—C2A—C7A—N8A | 178.65 (17) | C3B—C2B—C7B—N8B | 177.00 (18) |
N1A—C2A—C7A—N8A | −2.5 (3) | N1B—C2B—C7B—N8B | −4.7 (3) |
C5A—C6A—C7A—C2A | 2.1 (3) | C5B—C6B—C7B—C2B | 1.0 (3) |
C5A—C6A—C7A—N8A | −176.27 (19) | C5B—C6B—C7B—N8B | −177.37 (19) |
C2A—C7A—N8A—C9A | −133.1 (2) | C2B—C7B—N8B—C9B | 168.17 (19) |
C6A—C7A—N8A—C9A | 45.2 (3) | C6B—C7B—N8B—C9B | −13.5 (3) |
C7A—N8A—C9A—O10A | −3.8 (3) | C7B—N8B—C9B—O10B | −4.5 (3) |
C7A—N8A—C9A—C11A | 173.82 (18) | C7B—N8B—C9B—C11B | 176.59 (17) |
O10A—C9A—C11A—C12A | 4.9 (3) | O10B—C9B—C11B—C12B | −18.0 (3) |
N8A—C9A—C11A—C12A | −172.78 (19) | N8B—C9B—C11B—C12B | 160.96 (17) |
O10A—C9A—C11A—C16A | −177.4 (2) | O10B—C9B—C11B—C16B | 161.3 (2) |
N8A—C9A—C11A—C16A | 4.9 (3) | N8B—C9B—C11B—C16B | −19.7 (3) |
C16A—C11A—C12A—C13A | −0.5 (3) | C16B—C11B—C12B—C13B | 1.0 (3) |
C9A—C11A—C12A—C13A | 177.4 (2) | C9B—C11B—C12B—C13B | −179.7 (2) |
C11A—C12A—C13A—C14A | −1.3 (4) | C11B—C12B—C13B—C14B | 0.1 (4) |
C12A—C13A—C14A—C15A | 1.8 (4) | C12B—C13B—C14B—C15B | −0.5 (4) |
C13A—C14A—C15A—C16A | −0.5 (4) | C13B—C14B—C15B—C16B | −0.2 (4) |
C14A—C15A—C16A—O17A | 178.7 (2) | C14B—C15B—C16B—O17B | −177.97 (19) |
C14A—C15A—C16A—C11A | −1.3 (3) | C14B—C15B—C16B—C11B | 1.3 (3) |
C12A—C11A—C16A—O17A | −178.19 (19) | C12B—C11B—C16B—O17B | 177.64 (17) |
C9A—C11A—C16A—O17A | 4.2 (3) | C9B—C11B—C16B—O17B | −1.6 (3) |
C12A—C11A—C16A—C15A | 1.8 (3) | C12B—C11B—C16B—C15B | −1.6 (3) |
C9A—C11A—C16A—C15A | −175.8 (2) | C9B—C11B—C16B—C15B | 179.08 (19) |
C15A—C16A—O17A—C18A | −9.4 (3) | C15B—C16B—O17B—C18B | −1.1 (3) |
C11A—C16A—O17A—C18A | 170.6 (2) | C11B—C16B—O17B—C18B | 179.60 (18) |
C16A—O17A—C18A—C19A | −166.8 (2) | C16B—O17B—C18B—C19B | 151.96 (19) |
O17A—C18A—C19A—C20A | 93.2 (2) | O17B—C18B—C19B—C24B | 105.4 (2) |
O17A—C18A—C19A—C24A | −90.5 (3) | O17B—C18B—C19B—C20B | −79.0 (2) |
C24A—C19A—C20A—C21A | −0.9 (3) | C24B—C19B—C20B—C21B | −0.1 (3) |
C18A—C19A—C20A—C21A | 175.51 (19) | C18B—C19B—C20B—C21B | −175.94 (19) |
C19A—C20A—C21A—C22A | −0.7 (3) | C19B—C20B—C21B—C22B | −0.7 (3) |
C19A—C20A—C21A—C35A | 179.7 (2) | C19B—C20B—C21B—C35B | 179.1 (2) |
C20A—C21A—C22A—C23A | 2.0 (3) | C20B—C21B—C22B—C23B | 0.5 (3) |
C35A—C21A—C22A—C23A | −178.5 (2) | C35B—C21B—C22B—C23B | −179.3 (2) |
C20A—C21A—C22A—C36A | −178.3 (2) | C20B—C21B—C22B—C36B | 179.4 (2) |
C35A—C21A—C22A—C36A | 1.3 (3) | C35B—C21B—C22B—C36B | −0.4 (3) |
C21A—C22A—C23A—C24A | −1.7 (3) | C21B—C22B—C23B—C24B | 0.4 (3) |
C36A—C22A—C23A—C24A | 178.5 (2) | C36B—C22B—C23B—C24B | −178.5 (2) |
C22A—C23A—C24A—C19A | 0.1 (3) | C22B—C23B—C24B—C19B | −1.1 (3) |
C22A—C23A—C24A—C25A | −177.69 (18) | C22B—C23B—C24B—C25B | 174.56 (17) |
C20A—C19A—C24A—C23A | 1.2 (3) | C20B—C19B—C24B—C23B | 0.9 (3) |
C18A—C19A—C24A—C23A | −175.05 (17) | C18B—C19B—C24B—C23B | 176.48 (18) |
C20A—C19A—C24A—C25A | 178.83 (17) | C20B—C19B—C24B—C25B | −174.56 (17) |
C18A—C19A—C24A—C25A | 2.6 (3) | C18B—C19B—C24B—C25B | 1.0 (3) |
C23A—C24A—C25A—O26A | −92.3 (2) | C23B—C24B—C25B—O26B | 106.7 (2) |
C19A—C24A—C25A—O26A | 90.1 (2) | C19B—C24B—C25B—O26B | −77.8 (2) |
C24A—C25A—O26A—C27A | 163.72 (18) | C24B—C25B—O26B—C27B | −179.83 (18) |
C25A—O26A—C27A—C28A | 0.9 (3) | C25B—O26B—C27B—C28B | −1.5 (3) |
C25A—O26A—C27A—C32A | −178.26 (18) | C25B—O26B—C27B—C32B | 178.65 (19) |
O26A—C27A—C28A—C29A | −179.0 (2) | O26B—C27B—C28B—C29B | −178.41 (19) |
C32A—C27A—C28A—C29A | 0.2 (3) | C32B—C27B—C28B—C29B | 1.4 (3) |
C27A—C28A—C29A—C30A | −1.8 (4) | C27B—C28B—C29B—C30B | −1.8 (4) |
C28A—C29A—C30A—C31A | 2.2 (4) | C28B—C29B—C30B—C31B | 0.8 (4) |
C29A—C30A—C31A—C32A | −1.1 (4) | C29B—C30B—C31B—C32B | 0.6 (4) |
C30A—C31A—C32A—C27A | −0.4 (3) | O26B—C27B—C32B—C31B | 179.77 (18) |
C30A—C31A—C32A—C33A | 179.9 (2) | C28B—C27B—C32B—C31B | 0.0 (3) |
O26A—C27A—C32A—C31A | −179.93 (18) | O26B—C27B—C32B—C33B | 1.2 (3) |
C28A—C27A—C32A—C31A | 0.9 (3) | C28B—C27B—C32B—C33B | −178.6 (2) |
O26A—C27A—C32A—C33A | −0.3 (3) | C30B—C31B—C32B—C27B | −1.0 (3) |
C28A—C27A—C32A—C33A | −179.5 (2) | C30B—C31B—C32B—C33B | 177.8 (2) |
C2A—N1A—C33A—O34A | −0.9 (3) | C2B—N1B—C33B—O34B | 2.7 (4) |
C2A—N1A—C33A—C32A | −179.15 (17) | C2B—N1B—C33B—C32B | −178.43 (18) |
C31A—C32A—C33A—O34A | −5.2 (3) | C27B—C32B—C33B—O34B | 179.0 (2) |
C27A—C32A—C33A—O34A | 175.2 (2) | C31B—C32B—C33B—O34B | 0.3 (3) |
C31A—C32A—C33A—N1A | 173.10 (19) | C27B—C32B—C33B—N1B | 0.1 (3) |
C27A—C32A—C33A—N1A | −6.5 (3) | C31B—C32B—C33B—N1B | −178.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O26A | 0.86 | 2.01 | 2.691 (2) | 135 |
N1B—H1B···O26B | 0.86 | 2.00 | 2.662 (2) | 134 |
N8A—H8A···O17A | 0.86 | 1.99 | 2.677 (2) | 136 |
N8B—H8B···O17B | 0.86 | 2.10 | 2.722 (2) | 129 |
N8B—H8B···N1B | 0.86 | 2.42 | 2.791 (3) | 106 |
C3A—H3A···O34A | 0.93 | 2.41 | 2.809 (4) | 106 |
C6A—H6A···O10A | 0.93 | 2.53 | 2.866 (4) | 102 |
C6B—H6B···O10B | 0.93 | 2.24 | 2.820 (3) | 120 |
C12A—H12A···O10A | 0.93 | 2.34 | 2.694 (3) | 102 |
C12B—H12B···O10B | 0.93 | 2.38 | 2.719 (3) | 101 |
C15A—H15A···O10B | 0.93 | 2.59 | 3.517 (3) | 173 |
C28A—H28A···O34B | 0.93 | 2.25 | 3.132 (3) | 156 |
C15B—H15B···O10Ai | 0.93 | 2.49 | 3.376 (3) | 158 |
C18B—H18C···O10Ai | 0.97 | 2.33 | 3.233 (3) | 154 |
C25B—H25C···O34Ai | 0.97 | 2.59 | 3.052 (3) | 109 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C30H26N2O4 |
Mr | 478.53 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 15.5767 (9), 15.7746 (9), 20.5721 (12) |
β (°) | 102.541 (1) |
V (Å3) | 4934.3 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.20 × 0.16 |
|
Data collection |
Diffractometer | CCD Area Detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30895, 11480, 6259 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.662 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.166, 0.99 |
No. of reflections | 11480 |
No. of parameters | 653 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.22 |
Selected geometric parameters (Å, º) topN1A—C33A | 1.342 (3) | N1B—C33B | 1.336 (2) |
N1A—C2A | 1.418 (2) | N1B—C2B | 1.434 (2) |
C7A—N8A | 1.426 (2) | C7B—N8B | 1.409 (2) |
N8A—C9A | 1.348 (3) | N8B—C9B | 1.348 (2) |
C9A—O10A | 1.213 (2) | C9B—O10B | 1.218 (2) |
C33A—O34A | 1.220 (2) | C33B—O34B | 1.208 (2) |
| | | |
O17A—C16A—C15A | 122.5 (2) | O17B—C16B—C15B | 122.9 (2) |
O17A—C16A—C11A | 117.2 (2) | O17B—C16B—C11B | 117.8 (2) |
C23A—C24A—C25A | 117.3 (2) | C23B—C24B—C25B | 118.9 (2) |
C19A—C24A—C25A | 124.5 (2) | C19B—C24B—C25B | 122.6 (2) |
| | | |
C33A—N1A—C2A—C3A | −40.3 (3) | C33B—N1B—C2B—C3B | 64.6 (3) |
C6A—C7A—N8A—C9A | 45.2 (3) | C6B—C7B—N8B—C9B | −13.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O26A | 0.86 | 2.01 | 2.691 (2) | 135 |
N1B—H1B···O26B | 0.86 | 2.00 | 2.662 (2) | 134 |
N8A—H8A···O17A | 0.86 | 1.99 | 2.677 (2) | 136 |
N8B—H8B···O17B | 0.86 | 2.10 | 2.722 (2) | 129 |
N8B—H8B···N1B | 0.86 | 2.42 | 2.791 (3) | 106 |
C3A—H3A···O34A | 0.93 | 2.41 | 2.809 (4) | 106 |
C6A—H6A···O10A | 0.93 | 2.53 | 2.866 (4) | 102 |
C6B—H6B···O10B | 0.93 | 2.24 | 2.820 (3) | 120 |
C12A—H12A···O10A | 0.93 | 2.34 | 2.694 (3) | 102 |
C12B—H12B···O10B | 0.93 | 2.38 | 2.719 (3) | 101 |
C15A—H15A···O10B | 0.93 | 2.59 | 3.517 (3) | 173 |
C28A—H28A···O34B | 0.93 | 2.25 | 3.132 (3) | 156 |
C15B—H15B···O10Ai | 0.93 | 2.49 | 3.376 (3) | 158 |
C18B—H18C···O10Ai | 0.97 | 2.33 | 3.233 (3) | 154 |
C25B—H25C···O34Ai | 0.97 | 2.59 | 3.052 (3) | 109 |
Symmetry code: (i) x−1, y, z. |
Cyclophane derivatives constitute a novel building block for the potent human immuno deficiency virus (HIV) protease inhibitor (Ettmayer et al., 1996). Cyclophane derivatives act catalytically as cholesterol shuttles to accelerate the exchange of free cholesterol between cells and serum lipo proteins (Christian et al., 1999). Cyclophane derivatives act as potential reversal agents of muscle relaxants by chemical chelation (Cameron et al., 2002). The importance of cyclophane derivatives prompted us to undertake the structure analysis of the title compound, (I).
The asymmetric unit of (I) contains two molecules (A and B), with similar bond lengths and angles.
The C—C bond lengths in the phenyl rings (A, B, C and D) are comparable to the reported literature value of 1.384 (13) Å. All of the C—N bond lengths in both of the molecules also agree with the reported literature values [Csp2—N = 1.339 (16) Å and Cphenyl—N = 1.419 (17) Å; Allen et al., 1987].
The exocyclic angles around atoms C16 and C24 show considerable asymmetry, with the O17—C16—C15 angle [122.4 (2)° for molecule A and 122.9 (2)° for molecule B] being wider than the O17—C16—C11 angle [117.2 (2)° for molecule A and 117.8 (2)° for molecule B], and the C19—C24—C25 angle [124.5 (2)° for molecule A and 122.6 (2)° for molecule B] being wider than the C23—C24—C25 angle [117.3 (2) for molecule A and 118.9 (2)° for molecule B]. This asymmetry may be due to the short contacts between H15A—H18B (2.19 Å), H15B—H18C (1.90 Å), H18A—H25B (2.11 Å) and H25C—H18B (2.14 Å).
The values of the C33—N1—C2—C3 [−40.3 (3) for molecule A and 64.6 (3) for molecule B] and C6—C7—N8—C9 [45.2 (3) for molecule A and −13.5 (3) for molecule B] torsion angles indicate that the two amide groups are twisted from the plane of phenyl ring A, with dihedral angles of 39.6 (1) and 44.3 (2)° for molecule A and 66.5 (2) and 14.9 (1)° for molecule B.
Rings B and D are perpendicular to one another, the dihedral angle between their planes being 87.0 (1)° for molecule A and 90.0 (1)° for molecule B. The dihedral angle between rings B and C is 84.8 (1)° for molecule A and 86.8 (1)° for molecule B, indicating that these two phenyl rings are almost perpendicular to one another.
In addition to the van der Waals interactions, the molecular structure is influenced by N—H···O, N—H···N and C—H···O intramolecular interactions. The packing of the molecule is stabilized by C—H···O intermolecular interactions which run along the ab plane (Fig. 2). In addition, symmetry-related molecules are also linked by weak C—H···π intermolecular interactions, such that atom H5B is 2.91 Å from the centroid of ring D at (3/2 − x,1/2 + y,1/2 − z), with a C5—H5B···Centroid angle of 161° and a C5—H5B···Centroid distance of 3.801 (3) Å.