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The title compound, C
31H
26N
2O
5, is a compound with a spiro junction between β-lactam and isatin ring systems. Its four- and five-membered rings are nearly planar, with maximum deviations of −0.020 (1) and 0.050 (1) Å for their carbonyl C atoms, respectively. The dihedral angle between these two rings is 86.44 (5)°. The crystal structure is stabilized by intramolecular C—H
O hydrogen-bonding and van der Waals interactions.
Supporting information
CCDC reference: 298560
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.102
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1'-Benzyl-1-(2,4-dimethoxyphenyl)-3-phenoxyspiro[azetidine-2,3'(3
H)-
indole]-2',4(1
H)-dione
top
Crystal data top
C31H26N2O5 | F(000) = 1064 |
Mr = 506.54 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 29809 reflections |
a = 9.3547 (7) Å | θ = 1.5–27.3° |
b = 10.0777 (5) Å | µ = 0.09 mm−1 |
c = 28.193 (2) Å | T = 296 K |
β = 106.838 (5)° | Prism, colourless |
V = 2543.9 (3) Å3 | 0.65 × 0.50 × 0.29 mm |
Z = 4 | |
Data collection top
Stoe IPDS2 diffractometer | 3963 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.042 |
Plane graphite monochromator | θmax = 26.0°, θmin = 1.5° |
Detector resolution: 6.67 pixels mm-1 | h = −11→11 |
ω scans | k = −12→12 |
26901 measured reflections | l = −34→32 |
4995 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) = 0.102 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3 |
4995 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | 0.95416 (14) | 0.67625 (14) | 0.19705 (4) | 0.0786 (5) | |
O2 | 0.55625 (10) | 0.71175 (11) | 0.26976 (3) | 0.0596 (3) | |
O3 | 0.80723 (12) | 0.35519 (10) | 0.38761 (4) | 0.0621 (3) | |
O4 | 0.76729 (10) | 0.57925 (10) | 0.45598 (3) | 0.0544 (3) | |
O5 | 0.36250 (10) | 0.53244 (10) | 0.33181 (4) | 0.0583 (3) | |
N1 | 0.69568 (11) | 0.54774 (10) | 0.34503 (4) | 0.0442 (3) | |
N2 | 0.38854 (12) | 0.75608 (11) | 0.34947 (4) | 0.0496 (3) | |
C1 | 0.75775 (13) | 0.57277 (12) | 0.30565 (4) | 0.0427 (3) | |
C2 | 0.69042 (14) | 0.66317 (13) | 0.26816 (4) | 0.0469 (4) | |
C3 | 0.76040 (16) | 0.69623 (15) | 0.23289 (5) | 0.0550 (5) | |
C4 | 0.89409 (16) | 0.63559 (15) | 0.23342 (5) | 0.0552 (5) | |
C5 | 0.95712 (16) | 0.54108 (15) | 0.26855 (5) | 0.0555 (4) | |
C6 | 0.88915 (15) | 0.51206 (13) | 0.30494 (5) | 0.0501 (4) | |
C7 | 0.4928 (2) | 0.8191 (2) | 0.23834 (7) | 0.0902 (8) | |
C8 | 1.0946 (2) | 0.6237 (2) | 0.19742 (7) | 0.0877 (8) | |
C9 | 0.73437 (14) | 0.45600 (13) | 0.38230 (5) | 0.0479 (4) | |
C10 | 0.65669 (14) | 0.53296 (13) | 0.41431 (4) | 0.0478 (4) | |
C11 | 0.60872 (13) | 0.63263 (12) | 0.36927 (4) | 0.0427 (3) | |
C12 | 0.64376 (13) | 0.77630 (13) | 0.37747 (4) | 0.0443 (4) | |
C13 | 0.50926 (14) | 0.84504 (13) | 0.36617 (5) | 0.0481 (4) | |
C14 | 0.50455 (17) | 0.98114 (14) | 0.36987 (6) | 0.0620 (5) | |
C15 | 0.64002 (19) | 1.04751 (15) | 0.38574 (6) | 0.0672 (6) | |
C16 | 0.77351 (17) | 0.98085 (15) | 0.39705 (6) | 0.0623 (5) | |
C17 | 0.77726 (15) | 0.84352 (14) | 0.39294 (5) | 0.0527 (4) | |
C18 | 0.43872 (14) | 0.63018 (13) | 0.34634 (4) | 0.0453 (4) | |
C19 | 0.23167 (15) | 0.79080 (15) | 0.34186 (5) | 0.0564 (4) | |
C20 | 0.19641 (14) | 0.80358 (14) | 0.39054 (5) | 0.0531 (4) | |
C21 | 0.18966 (17) | 0.92623 (16) | 0.41186 (7) | 0.0661 (5) | |
C22 | 0.1649 (2) | 0.93601 (19) | 0.45779 (7) | 0.0764 (6) | |
C23 | 0.14289 (19) | 0.8231 (2) | 0.48240 (7) | 0.0743 (6) | |
C24 | 0.14658 (18) | 0.70103 (18) | 0.46115 (6) | 0.0689 (6) | |
C25 | 0.17384 (16) | 0.69098 (15) | 0.41587 (6) | 0.0600 (5) | |
C26 | 0.72311 (15) | 0.63499 (13) | 0.49433 (5) | 0.0494 (4) | |
C27 | 0.58004 (17) | 0.67325 (16) | 0.49109 (5) | 0.0612 (5) | |
C28 | 0.54888 (19) | 0.72269 (17) | 0.53283 (6) | 0.0695 (6) | |
C29 | 0.6591 (2) | 0.73257 (17) | 0.57692 (6) | 0.0709 (6) | |
C30 | 0.8030 (2) | 0.69784 (16) | 0.57925 (6) | 0.0682 (5) | |
C31 | 0.83645 (17) | 0.64991 (14) | 0.53810 (5) | 0.0580 (4) | |
H3 | 0.71800 | 0.75910 | 0.20880 | 0.0660* | |
H5 | 1.04400 | 0.49740 | 0.26790 | 0.0670* | |
H6 | 0.93310 | 0.45040 | 0.32940 | 0.0600* | |
H7A | 0.47170 | 0.79190 | 0.20440 | 0.1080* | |
H7B | 0.56170 | 0.89210 | 0.24450 | 0.1080* | |
H7C | 0.40180 | 0.84630 | 0.24480 | 0.1080* | |
H8A | 1.08640 | 0.52940 | 0.19270 | 0.1050* | |
H8B | 1.16640 | 0.64290 | 0.22870 | 0.1050* | |
H8C | 1.12640 | 0.66320 | 0.17120 | 0.1050* | |
H10 | 0.57390 | 0.48590 | 0.42170 | 0.0570* | |
H14 | 0.41430 | 1.02670 | 0.36200 | 0.0740* | |
H15 | 0.64030 | 1.13940 | 0.38880 | 0.0810* | |
H16 | 0.86250 | 1.02810 | 0.40760 | 0.0750* | |
H17 | 0.86770 | 0.79820 | 0.40040 | 0.0630* | |
H19A | 0.16860 | 0.72290 | 0.32190 | 0.0680* | |
H19B | 0.21010 | 0.87410 | 0.32400 | 0.0680* | |
H21 | 0.20190 | 1.00300 | 0.39510 | 0.0790* | |
H22 | 0.16310 | 1.01890 | 0.47210 | 0.0920* | |
H23 | 0.12570 | 0.82960 | 0.51320 | 0.0890* | |
H24 | 0.13060 | 0.62470 | 0.47740 | 0.0830* | |
H25 | 0.17720 | 0.60770 | 0.40200 | 0.0720* | |
H27 | 0.50490 | 0.66610 | 0.46120 | 0.0730* | |
H28 | 0.45220 | 0.74940 | 0.53090 | 0.0830* | |
H29 | 0.63660 | 0.76260 | 0.60510 | 0.0850* | |
H30 | 0.87840 | 0.70690 | 0.60890 | 0.0820* | |
H31 | 0.93420 | 0.62780 | 0.53970 | 0.0700* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0800 (8) | 0.1029 (9) | 0.0666 (7) | 0.0120 (7) | 0.0429 (6) | 0.0176 (6) |
O2 | 0.0524 (5) | 0.0734 (7) | 0.0540 (5) | 0.0198 (5) | 0.0172 (4) | 0.0191 (5) |
O3 | 0.0726 (6) | 0.0502 (6) | 0.0650 (6) | 0.0150 (5) | 0.0222 (5) | 0.0123 (4) |
O4 | 0.0477 (5) | 0.0716 (6) | 0.0419 (5) | 0.0029 (4) | 0.0099 (4) | 0.0010 (4) |
O5 | 0.0511 (5) | 0.0541 (6) | 0.0667 (6) | −0.0073 (4) | 0.0123 (4) | −0.0100 (5) |
N1 | 0.0462 (5) | 0.0439 (5) | 0.0435 (5) | 0.0057 (4) | 0.0146 (4) | 0.0040 (4) |
N2 | 0.0397 (5) | 0.0485 (6) | 0.0591 (6) | 0.0021 (5) | 0.0120 (5) | −0.0014 (5) |
C1 | 0.0437 (6) | 0.0441 (6) | 0.0398 (6) | −0.0016 (5) | 0.0111 (5) | −0.0011 (5) |
C2 | 0.0446 (6) | 0.0526 (7) | 0.0422 (6) | 0.0033 (5) | 0.0105 (5) | 0.0001 (5) |
C3 | 0.0579 (8) | 0.0640 (9) | 0.0433 (7) | 0.0039 (7) | 0.0148 (6) | 0.0083 (6) |
C4 | 0.0568 (8) | 0.0668 (9) | 0.0457 (7) | −0.0028 (7) | 0.0208 (6) | −0.0013 (6) |
C5 | 0.0499 (7) | 0.0625 (8) | 0.0571 (8) | 0.0037 (6) | 0.0204 (6) | −0.0031 (6) |
C6 | 0.0490 (7) | 0.0521 (7) | 0.0483 (7) | 0.0047 (6) | 0.0126 (5) | 0.0036 (6) |
C7 | 0.0831 (12) | 0.1040 (15) | 0.0881 (12) | 0.0444 (11) | 0.0323 (10) | 0.0472 (11) |
C8 | 0.0815 (12) | 0.1158 (16) | 0.0823 (12) | 0.0073 (11) | 0.0500 (10) | 0.0075 (11) |
C9 | 0.0495 (7) | 0.0447 (7) | 0.0481 (7) | 0.0010 (6) | 0.0118 (5) | 0.0049 (5) |
C10 | 0.0472 (7) | 0.0515 (7) | 0.0434 (6) | −0.0008 (6) | 0.0112 (5) | 0.0045 (5) |
C11 | 0.0424 (6) | 0.0445 (6) | 0.0413 (6) | 0.0018 (5) | 0.0124 (5) | 0.0006 (5) |
C12 | 0.0438 (6) | 0.0462 (7) | 0.0433 (6) | 0.0001 (5) | 0.0131 (5) | 0.0004 (5) |
C13 | 0.0462 (7) | 0.0462 (7) | 0.0534 (7) | −0.0007 (5) | 0.0168 (5) | 0.0003 (5) |
C14 | 0.0580 (8) | 0.0474 (8) | 0.0835 (10) | 0.0049 (6) | 0.0250 (7) | 0.0001 (7) |
C15 | 0.0722 (10) | 0.0463 (8) | 0.0896 (11) | −0.0079 (7) | 0.0338 (9) | −0.0055 (7) |
C16 | 0.0567 (8) | 0.0584 (9) | 0.0746 (10) | −0.0143 (7) | 0.0235 (7) | −0.0095 (7) |
C17 | 0.0458 (7) | 0.0568 (8) | 0.0563 (7) | −0.0041 (6) | 0.0162 (6) | −0.0034 (6) |
C18 | 0.0448 (6) | 0.0478 (7) | 0.0430 (6) | −0.0002 (5) | 0.0124 (5) | −0.0010 (5) |
C19 | 0.0410 (7) | 0.0602 (8) | 0.0642 (8) | 0.0062 (6) | 0.0091 (6) | 0.0021 (7) |
C20 | 0.0367 (6) | 0.0543 (8) | 0.0663 (8) | 0.0034 (5) | 0.0119 (6) | −0.0021 (6) |
C21 | 0.0583 (8) | 0.0557 (9) | 0.0875 (11) | −0.0012 (7) | 0.0260 (8) | −0.0057 (8) |
C22 | 0.0713 (10) | 0.0709 (11) | 0.0906 (12) | −0.0057 (8) | 0.0290 (9) | −0.0259 (9) |
C23 | 0.0659 (10) | 0.0896 (13) | 0.0681 (10) | 0.0022 (9) | 0.0207 (8) | −0.0080 (9) |
C24 | 0.0636 (9) | 0.0708 (10) | 0.0734 (10) | 0.0080 (8) | 0.0214 (8) | 0.0089 (8) |
C25 | 0.0528 (8) | 0.0527 (8) | 0.0746 (9) | 0.0056 (6) | 0.0185 (7) | 0.0003 (7) |
C26 | 0.0550 (7) | 0.0491 (7) | 0.0430 (6) | 0.0016 (6) | 0.0127 (5) | 0.0050 (5) |
C27 | 0.0543 (8) | 0.0751 (10) | 0.0517 (7) | 0.0049 (7) | 0.0116 (6) | 0.0020 (7) |
C28 | 0.0687 (10) | 0.0733 (10) | 0.0703 (10) | 0.0088 (8) | 0.0263 (8) | −0.0039 (8) |
C29 | 0.0945 (12) | 0.0630 (9) | 0.0579 (9) | 0.0041 (9) | 0.0264 (8) | −0.0088 (7) |
C30 | 0.0828 (11) | 0.0607 (9) | 0.0510 (8) | 0.0063 (8) | 0.0036 (7) | −0.0058 (7) |
C31 | 0.0578 (8) | 0.0565 (8) | 0.0524 (7) | 0.0035 (6) | 0.0044 (6) | −0.0003 (6) |
Geometric parameters (Å, º) top
O1—C4 | 1.3671 (19) | C23—C24 | 1.373 (3) |
O1—C8 | 1.414 (2) | C24—C25 | 1.376 (2) |
O2—C2 | 1.3601 (17) | C26—C27 | 1.370 (2) |
O2—C7 | 1.415 (2) | C26—C31 | 1.383 (2) |
O3—C9 | 1.2083 (17) | C27—C28 | 1.385 (2) |
O4—C10 | 1.4015 (15) | C28—C29 | 1.370 (2) |
O4—C26 | 1.3836 (16) | C29—C30 | 1.374 (3) |
O5—C18 | 1.2154 (16) | C30—C31 | 1.374 (2) |
N1—C1 | 1.4166 (16) | C3—H3 | 0.9300 |
N1—C9 | 1.3673 (17) | C5—H5 | 0.9300 |
N1—C11 | 1.4774 (16) | C6—H6 | 0.9300 |
N2—C13 | 1.4116 (18) | C7—H7A | 0.9600 |
N2—C18 | 1.3645 (17) | C7—H7B | 0.9600 |
N2—C19 | 1.4627 (19) | C7—H7C | 0.9600 |
C1—C2 | 1.3993 (17) | C8—H8A | 0.9600 |
C1—C6 | 1.3784 (19) | C8—H8B | 0.9600 |
C2—C3 | 1.3804 (19) | C8—H8C | 0.9600 |
C3—C4 | 1.388 (2) | C10—H10 | 0.9800 |
C4—C5 | 1.378 (2) | C14—H14 | 0.9300 |
C5—C6 | 1.386 (2) | C15—H15 | 0.9300 |
C9—C10 | 1.5244 (18) | C16—H16 | 0.9300 |
C10—C11 | 1.5788 (16) | C17—H17 | 0.9300 |
C11—C12 | 1.4877 (18) | C19—H19A | 0.9700 |
C11—C18 | 1.5336 (18) | C19—H19B | 0.9700 |
C12—C13 | 1.3901 (19) | C21—H21 | 0.9300 |
C12—C17 | 1.3759 (19) | C22—H22 | 0.9300 |
C13—C14 | 1.3772 (19) | C23—H23 | 0.9300 |
C14—C15 | 1.388 (2) | C24—H24 | 0.9300 |
C15—C16 | 1.372 (2) | C25—H25 | 0.9300 |
C16—C17 | 1.390 (2) | C27—H27 | 0.9300 |
C19—C20 | 1.5071 (19) | C28—H28 | 0.9300 |
C20—C21 | 1.384 (2) | C29—H29 | 0.9300 |
C20—C25 | 1.389 (2) | C30—H30 | 0.9300 |
C21—C22 | 1.383 (3) | C31—H31 | 0.9300 |
C22—C23 | 1.379 (3) | | |
| | | |
O2···C11 | 2.8195 (14) | C19···H14 | 2.8900 |
O2···N1 | 2.7079 (14) | C21···H14 | 3.0200 |
O2···N2 | 3.1231 (15) | C22···H16x | 2.9200 |
O2···C18 | 2.8145 (15) | C23···H28 | 2.9200 |
O2···C12 | 2.9790 (14) | C23···H17x | 2.9300 |
O2···C13 | 3.1746 (16) | C24···H17x | 2.8500 |
O3···O4 | 3.0612 (14) | C24···H28 | 3.0000 |
O3···C6 | 3.0909 (18) | C25···H27 | 3.0000 |
O3···C31i | 3.3846 (19) | C25···H17x | 2.9700 |
O4···N1 | 3.0200 (14) | C26···H24v | 2.9500 |
O4···O3 | 3.0612 (14) | C27···H10 | 2.7100 |
O4···C17 | 3.2181 (17) | C28···H10v | 2.8700 |
O5···N1 | 3.0338 (15) | C29···H21xi | 2.9700 |
O1···H30ii | 2.6500 | C31···H24v | 2.8300 |
O3···H15iii | 2.6800 | H3···C7 | 2.5500 |
O3···H31i | 2.6800 | H3···H7A | 2.3000 |
O3···H6 | 2.4700 | H3···H7B | 2.4100 |
O3···H8Civ | 2.7300 | H5···C8 | 2.5200 |
O4···H24v | 2.7600 | H5···H8A | 2.2900 |
O5···H10 | 2.7700 | H5···H8B | 2.3300 |
O5···H19A | 2.6000 | H6···O3 | 2.4700 |
O5···H7Bvi | 2.8300 | H6···C9 | 2.7000 |
N1···O2 | 2.7079 (14) | H7A···C3 | 2.7600 |
N1···O4 | 3.0200 (14) | H7A···H3 | 2.3000 |
N1···O5 | 3.0338 (15) | H7B···C3 | 2.7900 |
N1···C7vi | 3.397 (2) | H7B···H3 | 2.4100 |
N2···O2 | 3.1231 (15) | H7B···O5vii | 2.8300 |
C1···C7vi | 3.447 (2) | H7C···C1vii | 2.8700 |
C2···C12 | 3.4303 (16) | H8A···C5 | 2.7500 |
C6···O3 | 3.0909 (18) | H8A···H5 | 2.2900 |
C7···N1vii | 3.397 (2) | H8B···C5 | 2.7200 |
C7···C13 | 3.572 (2) | H8B···H5 | 2.3300 |
C7···C1vii | 3.447 (2) | H8C···O3viii | 2.7300 |
C8···C16iv | 3.549 (3) | H8C···C16iv | 3.0000 |
C11···C27 | 3.5453 (18) | H10···O5 | 2.7700 |
C11···O2 | 2.8195 (14) | H10···C27 | 2.7100 |
C12···C26 | 3.4665 (18) | H10···H27 | 2.3200 |
C12···C2 | 3.4303 (16) | H10···C28v | 2.8700 |
C12···C27 | 3.5779 (18) | H14···C19 | 2.8900 |
C12···O2 | 2.9790 (14) | H14···C21 | 3.0200 |
C13···O2 | 3.1746 (16) | H14···H19B | 2.4400 |
C13···C7 | 3.572 (2) | H14···H21 | 2.4400 |
C14···C21 | 3.522 (2) | H14···H29xi | 2.4200 |
C14···C20 | 3.581 (2) | H15···O3xii | 2.6800 |
C16···C8viii | 3.549 (3) | H16···C22ix | 2.9200 |
C16···C22ix | 3.593 (3) | H17···C23ix | 2.9300 |
C17···O4 | 3.2181 (17) | H17···C24ix | 2.8500 |
C18···O2 | 2.8145 (15) | H17···C25ix | 2.9700 |
C20···C14 | 3.581 (2) | H19A···O5 | 2.6000 |
C21···C14 | 3.522 (2) | H19A···C5x | 2.7900 |
C22···C16x | 3.593 (3) | H19A···H25 | 2.5200 |
C24···C31v | 3.540 (2) | H19B···C14 | 2.8900 |
C26···C12 | 3.4665 (18) | H19B···H14 | 2.4400 |
C27···C12 | 3.5779 (18) | H19B···H21 | 2.4100 |
C27···C11 | 3.5453 (18) | H19B···C4vii | 3.1000 |
C31···C24v | 3.540 (2) | H21···H14 | 2.4400 |
C31···O3i | 3.3846 (19) | H21···H19B | 2.4100 |
C1···H7Cvi | 2.8700 | H21···C29xi | 2.9700 |
C3···H7A | 2.7600 | H23···C16xi | 3.0900 |
C3···H7B | 2.7900 | H24···O4v | 2.7600 |
C4···H19Bvi | 3.1000 | H24···C26v | 2.9500 |
C5···H8A | 2.7500 | H24···C31v | 2.8300 |
C5···H8B | 2.7200 | H25···H19A | 2.5200 |
C5···H19Aix | 2.7900 | H27···C10 | 2.5800 |
C7···H3 | 2.5500 | H27···C11 | 3.0400 |
C8···H5 | 2.5200 | H27···C25 | 3.0000 |
C9···H6 | 2.7000 | H27···H10 | 2.3200 |
C10···H27 | 2.5800 | H28···C23 | 2.9200 |
C11···H27 | 3.0400 | H28···C24 | 3.0000 |
C14···H19B | 2.8900 | H29···C14xi | 3.0700 |
C14···H29xi | 3.0700 | H29···H14xi | 2.4200 |
C16···H23xi | 3.0900 | H30···O1xiii | 2.6500 |
C16···H8Cviii | 3.0000 | H31···O3i | 2.6800 |
| | | |
C4—O1—C8 | 117.72 (13) | C27—C28—C29 | 120.61 (17) |
C2—O2—C7 | 118.57 (12) | C28—C29—C30 | 119.64 (16) |
C10—O4—C26 | 118.37 (11) | C29—C30—C31 | 120.59 (16) |
C1—N1—C9 | 130.19 (11) | C26—C31—C30 | 119.25 (15) |
C1—N1—C11 | 131.68 (10) | C2—C3—H3 | 120.00 |
C9—N1—C11 | 95.44 (10) | C4—C3—H3 | 120.00 |
C13—N2—C18 | 110.80 (11) | C4—C5—H5 | 121.00 |
C13—N2—C19 | 124.66 (11) | C6—C5—H5 | 120.00 |
C18—N2—C19 | 124.21 (12) | C1—C6—H6 | 119.00 |
N1—C1—C2 | 120.72 (11) | C5—C6—H6 | 119.00 |
N1—C1—C6 | 120.14 (11) | O2—C7—H7A | 109.00 |
C2—C1—C6 | 119.09 (11) | O2—C7—H7B | 110.00 |
O2—C2—C1 | 115.28 (11) | O2—C7—H7C | 109.00 |
O2—C2—C3 | 124.87 (12) | H7A—C7—H7B | 109.00 |
C1—C2—C3 | 119.84 (13) | H7A—C7—H7C | 109.00 |
C2—C3—C4 | 119.99 (13) | H7B—C7—H7C | 109.00 |
O1—C4—C3 | 115.14 (13) | O1—C8—H8A | 109.00 |
O1—C4—C5 | 124.28 (14) | O1—C8—H8B | 109.00 |
C3—C4—C5 | 120.59 (14) | O1—C8—H8C | 109.00 |
C4—C5—C6 | 119.05 (14) | H8A—C8—H8B | 109.00 |
C1—C6—C5 | 121.30 (12) | H8A—C8—H8C | 110.00 |
O3—C9—N1 | 132.69 (13) | H8B—C8—H8C | 109.00 |
O3—C9—C10 | 134.66 (13) | O4—C10—H10 | 115.00 |
N1—C9—C10 | 92.61 (10) | C9—C10—H10 | 115.00 |
O4—C10—C9 | 107.63 (11) | C11—C10—H10 | 115.00 |
O4—C10—C11 | 115.55 (10) | C13—C14—H14 | 121.00 |
C9—C10—C11 | 85.45 (9) | C15—C14—H14 | 121.00 |
N1—C11—C10 | 86.41 (9) | C14—C15—H15 | 119.00 |
N1—C11—C12 | 120.62 (10) | C16—C15—H15 | 119.00 |
N1—C11—C18 | 116.00 (10) | C15—C16—H16 | 120.00 |
C10—C11—C12 | 119.72 (9) | C17—C16—H16 | 120.00 |
C10—C11—C18 | 110.32 (10) | C12—C17—H17 | 121.00 |
C12—C11—C18 | 103.65 (10) | C16—C17—H17 | 121.00 |
C11—C12—C13 | 107.78 (11) | N2—C19—H19A | 109.00 |
C11—C12—C17 | 131.86 (12) | N2—C19—H19B | 109.00 |
C13—C12—C17 | 120.36 (12) | C20—C19—H19A | 109.00 |
N2—C13—C12 | 110.09 (11) | C20—C19—H19B | 109.00 |
N2—C13—C14 | 128.15 (13) | H19A—C19—H19B | 108.00 |
C12—C13—C14 | 121.71 (13) | C20—C21—H21 | 120.00 |
C13—C14—C15 | 117.27 (14) | C22—C21—H21 | 120.00 |
C14—C15—C16 | 121.59 (14) | C21—C22—H22 | 120.00 |
C15—C16—C17 | 120.76 (15) | C23—C22—H22 | 120.00 |
C12—C17—C16 | 118.30 (13) | C22—C23—H23 | 120.00 |
O5—C18—N2 | 126.59 (13) | C24—C23—H23 | 120.00 |
O5—C18—C11 | 126.20 (12) | C23—C24—H24 | 120.00 |
N2—C18—C11 | 106.97 (11) | C25—C24—H24 | 120.00 |
N2—C19—C20 | 111.21 (11) | C20—C25—H25 | 119.00 |
C19—C20—C21 | 121.43 (13) | C24—C25—H25 | 120.00 |
C19—C20—C25 | 120.29 (13) | C26—C27—H27 | 120.00 |
C21—C20—C25 | 118.26 (14) | C28—C27—H27 | 121.00 |
C20—C21—C22 | 120.75 (16) | C27—C28—H28 | 120.00 |
C21—C22—C23 | 120.14 (17) | C29—C28—H28 | 120.00 |
C22—C23—C24 | 119.57 (17) | C28—C29—H29 | 120.00 |
C23—C24—C25 | 120.37 (16) | C30—C29—H29 | 120.00 |
C20—C25—C24 | 120.89 (15) | C29—C30—H30 | 120.00 |
O4—C26—C27 | 124.70 (12) | C31—C30—H30 | 120.00 |
O4—C26—C31 | 114.60 (13) | C26—C31—H31 | 120.00 |
C27—C26—C31 | 120.71 (13) | C30—C31—H31 | 120.00 |
C26—C27—C28 | 119.12 (14) | | |
| | | |
C8—O1—C4—C3 | 176.41 (14) | N1—C9—C10—O4 | −113.01 (11) |
C8—O1—C4—C5 | −4.0 (2) | C9—C10—C11—C12 | −125.69 (12) |
C7—O2—C2—C1 | 169.83 (13) | C9—C10—C11—C18 | 114.23 (10) |
C7—O2—C2—C3 | −10.5 (2) | O4—C10—C11—N1 | 105.18 (11) |
C26—O4—C10—C11 | 96.20 (13) | C9—C10—C11—N1 | −2.20 (9) |
C10—O4—C26—C27 | −13.86 (19) | O4—C10—C11—C18 | −138.39 (11) |
C10—O4—C26—C31 | 165.82 (12) | O4—C10—C11—C12 | −18.31 (17) |
C26—O4—C10—C9 | −170.38 (11) | C10—C11—C18—O5 | −53.77 (16) |
C9—N1—C11—C18 | −108.43 (11) | C12—C11—C18—O5 | 176.89 (12) |
C1—N1—C11—C18 | 89.26 (15) | N1—C11—C18—N2 | −142.96 (10) |
C9—N1—C11—C10 | 2.45 (10) | C12—C11—C18—N2 | −8.40 (12) |
C11—N1—C9—C10 | −2.54 (10) | N1—C11—C12—C13 | 138.12 (11) |
C11—N1—C1—C2 | −30.17 (19) | C10—C11—C12—C13 | −117.16 (12) |
C1—N1—C11—C12 | −37.17 (18) | C18—C11—C12—C17 | −173.55 (13) |
C1—N1—C11—C10 | −159.85 (13) | N1—C11—C18—O5 | 42.33 (17) |
C11—N1—C1—C6 | 147.17 (13) | C10—C11—C12—C17 | 63.08 (18) |
C1—N1—C9—C10 | 160.18 (12) | N1—C11—C12—C17 | −41.64 (18) |
C9—N1—C11—C12 | 125.14 (11) | C10—C11—C18—N2 | 120.94 (11) |
C9—N1—C1—C6 | −9.5 (2) | C18—C11—C12—C13 | 6.21 (12) |
C11—N1—C9—O3 | 179.69 (16) | C13—C12—C17—C16 | 0.23 (19) |
C9—N1—C1—C2 | 173.16 (13) | C17—C12—C13—C14 | 0.1 (2) |
C1—N1—C9—O3 | −17.6 (2) | C17—C12—C13—N2 | 177.78 (11) |
C18—N2—C19—C20 | 97.83 (14) | C11—C12—C17—C16 | 179.97 (12) |
C19—N2—C13—C14 | −12.7 (2) | C11—C12—C13—N2 | −2.01 (14) |
C13—N2—C19—C20 | −74.98 (16) | C11—C12—C13—C14 | −179.65 (13) |
C19—N2—C18—O5 | 8.6 (2) | C12—C13—C14—C15 | −0.4 (2) |
C18—N2—C13—C14 | 173.70 (14) | N2—C13—C14—C15 | −177.62 (14) |
C19—N2—C13—C12 | 169.89 (11) | C13—C14—C15—C16 | 0.4 (2) |
C13—N2—C18—O5 | −177.69 (12) | C14—C15—C16—C17 | 0.0 (3) |
C19—N2—C18—C11 | −166.05 (11) | C15—C16—C17—C12 | −0.3 (2) |
C13—N2—C18—C11 | 7.63 (13) | N2—C19—C20—C25 | −78.69 (17) |
C18—N2—C13—C12 | −3.75 (15) | N2—C19—C20—C21 | 99.51 (16) |
C6—C1—C2—O2 | 175.79 (11) | C21—C20—C25—C24 | −0.5 (2) |
N1—C1—C6—C5 | −175.93 (12) | C19—C20—C21—C22 | −176.59 (15) |
C2—C1—C6—C5 | 1.5 (2) | C19—C20—C25—C24 | 177.78 (14) |
N1—C1—C2—O2 | −6.85 (17) | C25—C20—C21—C22 | 1.6 (2) |
N1—C1—C2—C3 | 173.51 (12) | C20—C21—C22—C23 | −1.6 (3) |
C6—C1—C2—C3 | −3.86 (19) | C21—C22—C23—C24 | 0.4 (3) |
O2—C2—C3—C4 | −176.86 (13) | C22—C23—C24—C25 | 0.8 (3) |
C1—C2—C3—C4 | 2.8 (2) | C23—C24—C25—C20 | −0.7 (3) |
C2—C3—C4—C5 | 0.8 (2) | C27—C26—C31—C30 | 3.1 (2) |
C2—C3—C4—O1 | −179.61 (13) | O4—C26—C31—C30 | −176.60 (13) |
C3—C4—C5—C6 | −3.2 (2) | C31—C26—C27—C28 | −2.4 (2) |
O1—C4—C5—C6 | 177.25 (14) | O4—C26—C27—C28 | 177.27 (14) |
C4—C5—C6—C1 | 2.1 (2) | C26—C27—C28—C29 | −0.4 (2) |
O3—C9—C10—O4 | 64.7 (2) | C27—C28—C29—C30 | 2.5 (3) |
N1—C9—C10—C11 | 2.37 (10) | C28—C29—C30—C31 | −1.8 (3) |
O3—C9—C10—C11 | −179.93 (17) | C29—C30—C31—C26 | −1.0 (2) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y−1, z; (iv) −x+2, y−1/2, −z+1/2; (v) −x+1, −y+1, −z+1; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+2, y+1/2, −z+1/2; (ix) x+1, y, z; (x) x−1, y, z; (xi) −x+1, −y+2, −z+1; (xii) x, y+1, z; (xiii) x, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3 | 0.93 | 2.47 | 3.0909 (18) | 124 |
C19—H19A···O5 | 0.97 | 2.60 | 2.9254 (18) | 100 |
Dihedral angles (°) between the planes of the ring systems of (I) topRings | A | B | C | D | E |
A | | 26.81 (5) | 84.60 (5) | 35.01 (6) | 54.04 (5) |
B | | | 69.26 (4) | 57.04 (5) | 51.12 (5) |
C | | | | 81.68 (4) | 64.88 (4) |
D | | | | | 85.54 (5) |
The ring systems are A (N1/C9–C11), B (C1–C6), C (C13–C17/C12/C11/C18/N2),
D (C20–C25) and E (C26–C31). |
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