In the title compound, C18H26N4O4, the bridgehead N atom is located toward the inside of the cage and the displacement from the aromatic ring is 4.2110 (13) Å. The three C atoms adjacent to the bridgehead N atom are disordered with roughly equal occupancy between two sets of positions.
Supporting information
CCDC reference: 177219
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.116
- Data-to-parameter ratio = 14.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Siemens, 1996); cell refinement: SAINT; data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2001).
3,5,8,19-Tetraaza-2,9,18-trione-[5
5,13][11]metacyclophane monohydrate
top
Crystal data top
C18H24N4O3·H2O | F(000) = 776 |
Mr = 362.43 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 11459 reflections |
a = 9.3436 (8) Å | θ = 2.1–28.3° |
b = 13.4554 (12) Å | µ = 0.10 mm−1 |
c = 14.2888 (12) Å | T = 298 K |
β = 94.748 (2)° | Plate, colorless |
V = 1790.3 (3) Å3 | 0.5 × 0.35 × 0.25 mm |
Z = 4 | |
Data collection top
CCD area detector diffractometer | 2794 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
Graphite monochromator | θmax = 28.3°, θmin = 2.1° |
φ and ω scans | h = −12→8 |
11459 measured reflections | k = −17→17 |
4316 independent reflections | l = −18→19 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0871P] where P = (Fo2 + 2Fc2)/3 |
4316 reflections | (Δ/σ)max = 0.002 |
295 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 | Occ. (<1) |
O1 | 0.30412 (14) | 1.00794 (9) | −0.07705 (8) | 0.0657 (5) | |
O2 | 0.55060 (12) | 0.71597 (10) | 0.38548 (7) | 0.0586 (4) | |
O3 | 0.10149 (13) | 0.51426 (10) | 0.14048 (9) | 0.0628 (5) | |
N | 0.11802 (11) | 0.81686 (9) | 0.17809 (8) | 0.0352 (4) | |
N1 | 0.28539 (15) | 0.91248 (11) | 0.04910 (9) | 0.0460 (4) | |
N2 | 0.37479 (13) | 0.73510 (11) | 0.27019 (9) | 0.0449 (5) | |
N3 | 0.05146 (14) | 0.64347 (10) | 0.04433 (9) | 0.0416 (4) | |
C1 | 0.1412 (3) | 0.9259 (2) | 0.1779 (2) | 0.0442 (10) | 0.527 (3) |
C2 | 0.1199 (3) | 0.7762 (3) | 0.26965 (19) | 0.0457 (10) | 0.527 (3) |
C3 | −0.0214 (3) | 0.7968 (2) | 0.1207 (2) | 0.0430 (10) | 0.527 (3) |
C4 | 0.17556 (18) | 0.96932 (13) | 0.09021 (13) | 0.0517 (5) | |
C5 | 0.26724 (17) | 0.77481 (13) | 0.32671 (10) | 0.0476 (5) | |
C6 | −0.05292 (15) | 0.68939 (13) | 0.09992 (11) | 0.0448 (5) | |
C7 | 0.33745 (16) | 0.93241 (12) | −0.03227 (10) | 0.0419 (5) | |
C8 | 0.50883 (16) | 0.71157 (11) | 0.30184 (10) | 0.0397 (5) | |
C9 | 0.12280 (15) | 0.56057 (11) | 0.06912 (10) | 0.0394 (5) | |
C10 | 0.44457 (17) | 0.85959 (12) | −0.06695 (10) | 0.0452 (5) | |
C11 | 0.61011 (15) | 0.67943 (13) | 0.22977 (10) | 0.0440 (5) | |
C12 | 0.23802 (16) | 0.52953 (12) | 0.00620 (10) | 0.0427 (5) | |
C13 | 0.45930 (15) | 0.76359 (11) | −0.01214 (9) | 0.0365 (4) | |
C14 | 0.54648 (15) | 0.75839 (12) | 0.07174 (10) | 0.0381 (4) | |
C15 | 0.54160 (13) | 0.67648 (11) | 0.13075 (10) | 0.0365 (4) | |
C16 | 0.45057 (15) | 0.59806 (12) | 0.10344 (10) | 0.0375 (4) | |
C17 | 0.36057 (14) | 0.60276 (11) | 0.02132 (9) | 0.0356 (4) | |
C18 | 0.36816 (15) | 0.68439 (11) | −0.03682 (10) | 0.0366 (4) | |
C1P | 0.0615 (4) | 0.9004 (3) | 0.1263 (3) | 0.0456 (11) | 0.473 (3) |
C2P | 0.1752 (3) | 0.8470 (3) | 0.2763 (2) | 0.0424 (10) | 0.473 (3) |
C3P | 0.0087 (3) | 0.7392 (3) | 0.1899 (2) | 0.0412 (10) | 0.473 (3) |
O1W | 0.3533 (2) | 1.05659 (15) | −0.26470 (12) | 0.0974 (8) | |
H1A | 0.05500 | 0.95780 | 0.19680 | 0.0530* | 0.527 (3) |
H1B | 0.21850 | 0.94150 | 0.22520 | 0.0530* | 0.527 (3) |
H2N | 0.3493 (19) | 0.7325 (14) | 0.2103 (13) | 0.060 (5)* | |
H3A | −0.09910 | 0.82390 | 0.15380 | 0.0520* | 0.527 (3) |
H3B | −0.02050 | 0.83220 | 0.06160 | 0.0520* | 0.527 (3) |
H3N | 0.0706 (19) | 0.6719 (14) | −0.0053 (14) | 0.059 (6)* | |
H1N | 0.3033 (19) | 0.8557 (15) | 0.0727 (13) | 0.063 (6)* | |
H2A | 0.08430 | 0.70850 | 0.26450 | 0.0550* | 0.527 (3) |
H2B | 0.05360 | 0.81380 | 0.30460 | 0.0550* | 0.527 (3) |
H5B | 0.26190 | 0.73420 | 0.38240 | 0.0570* | 0.527 (3) |
H6A | −0.05500 | 0.65350 | 0.15870 | 0.0540* | 0.527 (3) |
H6B | −0.14730 | 0.68400 | 0.06660 | 0.0540* | 0.527 (3) |
H10A | 0.41620 | 0.84400 | −0.13210 | 0.0540* | |
H10B | 0.53780 | 0.89160 | −0.06470 | 0.0540* | |
H11A | 0.69100 | 0.72480 | 0.23240 | 0.0530* | |
H11B | 0.64710 | 0.61380 | 0.24640 | 0.0530* | |
H12A | 0.27120 | 0.46290 | 0.02210 | 0.0510* | |
H12B | 0.19990 | 0.53010 | −0.05900 | 0.0510* | |
H14 | 0.6043 (17) | 0.8165 (12) | 0.0905 (11) | 0.044 (4)* | |
H16 | 0.4443 (15) | 0.5404 (12) | 0.1449 (10) | 0.038 (4)* | |
H18 | 0.3049 (16) | 0.6893 (11) | −0.0925 (11) | 0.041 (4)* | |
H4A | 0.20870 | 1.03700 | 0.10100 | 0.0620* | 0.527 (3) |
H4B | 0.08990 | 0.97140 | 0.04700 | 0.0620* | 0.527 (3) |
H5A | 0.29350 | 0.84180 | 0.34650 | 0.0570* | 0.527 (3) |
H4PA | 0.13050 | 1.01430 | 0.04360 | 0.0620* | 0.473 (3) |
H4PB | 0.21890 | 1.00880 | 0.14180 | 0.0620* | 0.473 (3) |
H5PA | 0.31440 | 0.80600 | 0.38220 | 0.0570* | 0.473 (3) |
H5PB | 0.20880 | 0.72070 | 0.34720 | 0.0570* | 0.473 (3) |
H6PA | −0.12080 | 0.63900 | 0.11610 | 0.0540* | 0.473 (3) |
H6PB | −0.10580 | 0.73870 | 0.06150 | 0.0540* | 0.473 (3) |
H11P | 0.00260 | 0.93870 | 0.16590 | 0.0550* | 0.473 (3) |
H12P | −0.00020 | 0.87680 | 0.07300 | 0.0550* | 0.473 (3) |
H21P | 0.22840 | 0.90850 | 0.27230 | 0.0510* | 0.473 (3) |
H22P | 0.09420 | 0.86040 | 0.31270 | 0.0510* | 0.473 (3) |
H31P | −0.06970 | 0.76890 | 0.22050 | 0.0500* | 0.473 (3) |
H32P | 0.05130 | 0.68840 | 0.23150 | 0.0500* | 0.473 (3) |
H1W | 0.346 (3) | 1.040 (2) | −0.208 (2) | 0.128 (11)* | |
H2W | 0.447 (5) | 1.038 (4) | −0.274 (3) | 0.21 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0837 (9) | 0.0546 (8) | 0.0609 (8) | 0.0104 (6) | 0.0190 (7) | 0.0241 (6) |
O2 | 0.0577 (7) | 0.0788 (9) | 0.0364 (6) | 0.0024 (6) | −0.0132 (5) | −0.0043 (5) |
O3 | 0.0653 (8) | 0.0652 (9) | 0.0595 (7) | 0.0076 (6) | 0.0151 (6) | 0.0227 (6) |
N | 0.0314 (6) | 0.0373 (7) | 0.0370 (6) | −0.0019 (5) | 0.0035 (5) | −0.0007 (5) |
N1 | 0.0525 (8) | 0.0406 (8) | 0.0466 (7) | 0.0089 (6) | 0.0147 (6) | 0.0100 (6) |
N2 | 0.0380 (7) | 0.0668 (10) | 0.0292 (6) | 0.0056 (6) | −0.0013 (5) | −0.0047 (6) |
N3 | 0.0437 (7) | 0.0427 (8) | 0.0381 (7) | −0.0018 (6) | 0.0010 (6) | 0.0016 (6) |
C1 | 0.0463 (17) | 0.0406 (18) | 0.0476 (17) | −0.0002 (13) | 0.0159 (15) | −0.0104 (13) |
C2 | 0.0443 (16) | 0.057 (2) | 0.0372 (15) | −0.0008 (15) | 0.0115 (12) | 0.0021 (14) |
C3 | 0.0336 (14) | 0.0476 (19) | 0.0473 (16) | 0.0026 (12) | −0.0002 (12) | −0.0006 (14) |
C4 | 0.0515 (9) | 0.0389 (9) | 0.0666 (10) | 0.0057 (7) | 0.0160 (8) | 0.0044 (8) |
C5 | 0.0452 (8) | 0.0643 (11) | 0.0331 (7) | 0.0002 (7) | 0.0029 (6) | −0.0076 (7) |
C6 | 0.0339 (7) | 0.0498 (10) | 0.0500 (9) | −0.0036 (7) | 0.0001 (6) | −0.0035 (7) |
C7 | 0.0443 (8) | 0.0411 (9) | 0.0402 (8) | −0.0076 (7) | 0.0027 (6) | 0.0053 (7) |
C8 | 0.0398 (8) | 0.0419 (9) | 0.0357 (7) | −0.0044 (6) | −0.0068 (6) | −0.0002 (6) |
C9 | 0.0372 (7) | 0.0398 (9) | 0.0398 (8) | −0.0089 (6) | −0.0053 (6) | −0.0019 (7) |
C10 | 0.0509 (9) | 0.0491 (10) | 0.0369 (8) | −0.0063 (7) | 0.0106 (7) | 0.0031 (7) |
C11 | 0.0307 (7) | 0.0566 (10) | 0.0432 (8) | 0.0023 (7) | −0.0056 (6) | −0.0007 (7) |
C12 | 0.0464 (8) | 0.0386 (9) | 0.0423 (8) | −0.0052 (7) | −0.0011 (6) | −0.0077 (7) |
C13 | 0.0344 (7) | 0.0412 (9) | 0.0350 (7) | 0.0002 (6) | 0.0095 (6) | −0.0014 (6) |
C14 | 0.0313 (7) | 0.0430 (9) | 0.0407 (7) | −0.0040 (6) | 0.0065 (6) | −0.0043 (7) |
C15 | 0.0268 (6) | 0.0455 (9) | 0.0372 (7) | 0.0037 (6) | 0.0022 (5) | −0.0033 (6) |
C16 | 0.0394 (8) | 0.0356 (8) | 0.0375 (7) | 0.0031 (6) | 0.0023 (6) | 0.0009 (6) |
C17 | 0.0351 (7) | 0.0360 (8) | 0.0360 (7) | 0.0010 (6) | 0.0047 (6) | −0.0093 (6) |
C18 | 0.0350 (7) | 0.0444 (9) | 0.0303 (7) | 0.0007 (6) | 0.0029 (6) | −0.0034 (6) |
C1P | 0.0421 (19) | 0.045 (2) | 0.0498 (19) | 0.0079 (15) | 0.0040 (16) | 0.0041 (16) |
C2P | 0.0383 (17) | 0.048 (2) | 0.0412 (17) | −0.0008 (15) | 0.0055 (13) | −0.0125 (15) |
C3P | 0.0359 (15) | 0.048 (2) | 0.0406 (17) | −0.0072 (14) | 0.0082 (13) | −0.0013 (15) |
O1W | 0.1187 (15) | 0.1181 (16) | 0.0557 (9) | 0.0230 (11) | 0.0097 (9) | 0.0136 (9) |
Geometric parameters (Å, º) top
O1—C7 | 1.227 (2) | C16—C17 | 1.3873 (19) |
O2—C8 | 1.2276 (17) | C17—C18 | 1.383 (2) |
O3—C9 | 1.2252 (19) | C1—H1B | 0.9704 |
O1W—H1W | 0.85 (3) | C1—H1A | 0.9705 |
O1W—H2W | 0.93 (5) | C1P—H11P | 0.9696 |
N—C3 | 1.505 (3) | C1P—H12P | 0.9698 |
N—C1 | 1.483 (3) | C2—H2B | 0.9697 |
N—C2 | 1.417 (3) | C2—H2A | 0.9705 |
N—C3P | 1.481 (4) | C2P—H21P | 0.9694 |
N—C2P | 1.515 (3) | C2P—H22P | 0.9700 |
N—C1P | 1.423 (4) | C3—H3B | 0.9702 |
N1—C4 | 1.443 (2) | C3—H3A | 0.9698 |
N1—C7 | 1.324 (2) | C3P—H31P | 0.9698 |
N2—C8 | 1.3340 (19) | C3P—H32P | 0.9694 |
N2—C5 | 1.443 (2) | C4—H4B | 0.9699 |
N3—C6 | 1.446 (2) | C4—H4PA | 0.9699 |
N3—C9 | 1.332 (2) | C4—H4A | 0.9701 |
N1—H1N | 0.85 (2) | C4—H4PB | 0.9696 |
N2—H2N | 0.870 (18) | C5—H5A | 0.9701 |
N3—H3N | 0.84 (2) | C5—H5B | 0.9700 |
C1—C4 | 1.443 (3) | C5—H5PA | 0.9701 |
C1P—C4 | 1.534 (4) | C5—H5PB | 0.9698 |
C2—C5 | 1.541 (3) | C6—H6A | 0.9704 |
C2P—C5 | 1.449 (4) | C6—H6B | 0.9696 |
C3—C6 | 1.500 (3) | C6—H6PA | 0.9694 |
C3P—C6 | 1.520 (3) | C6—H6PB | 0.9700 |
C7—C10 | 1.513 (2) | C10—H10A | 0.9695 |
C8—C11 | 1.518 (2) | C10—H10B | 0.9699 |
C9—C12 | 1.517 (2) | C11—H11B | 0.9706 |
C10—C13 | 1.511 (2) | C11—H11A | 0.9699 |
C11—C15 | 1.504 (2) | C12—H12A | 0.9695 |
C12—C17 | 1.513 (2) | C12—H12B | 0.9695 |
C13—C18 | 1.391 (2) | C14—H14 | 0.975 (16) |
C13—C14 | 1.3940 (19) | C16—H16 | 0.981 (16) |
C14—C15 | 1.391 (2) | C18—H18 | 0.953 (15) |
C15—C16 | 1.391 (2) | | |
| | | |
O1···O1W | 2.834 (2) | H2A···C6 | 2.5964 |
O1W···O3i | 2.940 (2) | H2A···H10Aiv | 2.3522 |
O1W···O1 | 2.834 (2) | H2A···H6A | 2.0497 |
O2···C18ii | 3.3599 (19) | H2A···C10iv | 2.9774 |
O2···N3ii | 2.9540 (18) | H2B···H1A | 2.4760 |
O3···C3P | 3.242 (4) | H2B···H3A | 2.4876 |
O3···C2Piii | 3.228 (4) | H2B···C13iv | 3.0165 |
O3···O1Wiv | 2.940 (2) | H2B···C18iv | 2.9643 |
O1···H1W | 1.99 (3) | H2N···C14 | 2.835 (18) |
O1···H14v | 2.525 (16) | H2N···C15 | 2.330 (18) |
O1···H4B | 2.8244 | H2N···C16 | 2.596 (19) |
O1···H4PA | 2.4645 | H2N···H1N | 2.58 (3) |
O1···H4A | 2.7921 | H2N···N | 2.451 (18) |
O1···H10Bv | 2.7597 | H2W···O3i | 2.09 (5) |
O1W···H12Bvi | 2.5520 | H5PA···O2 | 2.5146 |
O2···H5PA | 2.5146 | H3A···H2B | 2.4876 |
O2···H5B | 2.7054 | H3A···H1A | 2.3559 |
O2···H3Nii | 2.17 (2) | H3B···C4 | 2.6083 |
O2···H3Bii | 2.7333 | H3B···O2vii | 2.7333 |
O2···H18ii | 2.692 (15) | H3B···H3N | 2.5348 |
O3···H6PA | 2.6707 | H3B···H4B | 2.1567 |
O3···H32P | 2.7391 | H3N···O2vii | 2.168 (19) |
O3···H5Aiii | 2.5203 | H3N···H3B | 2.5348 |
O3···H2Wiv | 2.09 (5) | H3N···H12B | 2.4171 |
O3···H1Biii | 2.6337 | H3N···C17 | 2.860 (18) |
O3···H21Piii | 2.4035 | H3N···C18 | 2.858 (18) |
O3···H6A | 2.4039 | H5PB···C3P | 2.8131 |
N···N1 | 2.8240 (18) | H5PB···C10iv | 3.0444 |
N···N2 | 2.8593 (17) | H5PB···H32P | 2.1645 |
N···N3 | 3.0473 (18) | H5PB···H10Biv | 2.5988 |
N1···C14 | 3.198 (2) | H4A···O1 | 2.7921 |
N1···C18 | 3.418 (2) | H4B···O1 | 2.8244 |
N1···N | 2.8240 (18) | H4B···H4Bxii | 2.2012 |
N2···N | 2.8593 (17) | H4B···C3 | 2.8091 |
N2···C14 | 3.3861 (19) | H4B···H3B | 2.1567 |
N2···C16 | 3.140 (2) | H6PA···O3 | 2.6707 |
N3···N | 3.0473 (18) | H6PA···H12Bix | 2.5078 |
N3···C18 | 3.3124 (19) | H6PA···C12ix | 3.0131 |
N3···O2vii | 2.9540 (18) | H5A···O3viii | 2.5203 |
N···H1N | 2.443 (18) | H5A···H12Aviii | 2.5949 |
N···H2N | 2.451 (18) | H5A···H1B | 2.2569 |
C2···C10iv | 3.479 (4) | H5A···C1 | 2.9226 |
C2P···O3viii | 3.228 (4) | H5B···O2 | 2.7054 |
C3P···O3 | 3.242 (4) | H6PB···H12P | 2.1039 |
C7···C7v | 3.595 (2) | H6PB···C1P | 2.7920 |
C9···C9ix | 3.328 (2) | H6A···H2A | 2.0497 |
C10···C2i | 3.479 (4) | H6A···C2 | 2.7351 |
C14···N2 | 3.3861 (19) | H6A···O3 | 2.4039 |
C14···N1 | 3.198 (2) | H6B···H12Aix | 2.5711 |
C16···N2 | 3.140 (2) | H6B···C14x | 3.0378 |
C18···N3 | 3.3124 (19) | H10A···H18 | 2.4149 |
C18···N1 | 3.418 (2) | H10A···C2i | 2.9413 |
C18···O2vii | 3.3599 (19) | H10A···H2Ai | 2.3522 |
C1···H5A | 2.9226 | H10A···H32Pi | 2.4473 |
C1P···H6PB | 2.7920 | H10A···C3Pi | 2.9720 |
C2···H10Aiv | 2.9413 | H10B···H5PBi | 2.5988 |
C2···H6A | 2.7351 | H10B···C7v | 2.9358 |
C2P···H4PB | 2.9546 | H10B···O1v | 2.7597 |
C2P···H16viii | 3.081 (16) | H10B···H14 | 2.4692 |
C3···H4B | 2.8091 | H11A···H14 | 2.4531 |
C3P···H11Ax | 3.0849 | H11A···H31Pxi | 2.3331 |
C3P···H5PB | 2.8131 | H11A···C3Pxi | 3.0849 |
C3P···H10Aiv | 2.9720 | H11B···H16 | 2.4929 |
C4···H21P | 2.7332 | H11P···H22P | 2.4383 |
C4···H3B | 2.6083 | H11P···H31P | 2.5243 |
C5···H32P | 2.6113 | H11P···H21P | 2.5292 |
C5···H1B | 2.6893 | H12A···H16 | 2.5124 |
C6···H2A | 2.5964 | H12A···H6Bix | 2.5711 |
C6···H12P | 2.6040 | H12A···H5Aiii | 2.5949 |
C7···H1W | 2.91 (3) | H12B···O1Wxiii | 2.5520 |
C7···H10Bv | 2.9358 | H12B···H6PAix | 2.5078 |
C9···H32P | 3.0074 | H12B···H3N | 2.4171 |
C10···H2Ai | 2.9774 | H12B···H18 | 2.4203 |
C10···H5PBi | 3.0444 | H12P···C6 | 2.6040 |
C12···H6PAix | 3.0131 | H12P···H6PB | 2.1039 |
C13···H2Bi | 3.0165 | H12P···H4PAxii | 2.4636 |
C13···H1N | 2.329 (19) | H14···H11A | 2.4531 |
C14···H6Bxi | 3.0378 | H14···O1v | 2.525 (16) |
C14···H2N | 2.835 (18) | H14···H1Wv | 2.58 (3) |
C14···H1N | 2.623 (19) | H14···H10B | 2.4692 |
C15···H2N | 2.330 (18) | H16···H22Piii | 2.5295 |
C16···H2N | 2.596 (19) | H16···H12A | 2.5124 |
C17···H3N | 2.860 (18) | H16···H1Aiii | 2.5197 |
C18···H3N | 2.858 (18) | H16···H11B | 2.4929 |
C18···H2Bi | 2.9643 | H16···C2Piii | 3.081 (16) |
C18···H1N | 2.88 (2) | H18···H12B | 2.4203 |
H4PA···H12Pxii | 2.4636 | H18···O2vii | 2.692 (15) |
H4PA···O1 | 2.4645 | H18···H10A | 2.4149 |
H1A···H2B | 2.4760 | H21P···H11P | 2.5292 |
H1A···H3A | 2.3559 | H21P···C4 | 2.7332 |
H1A···H16viii | 2.5197 | H21P···H4PB | 2.2976 |
H1B···C5 | 2.6893 | H21P···O3viii | 2.4035 |
H1B···O3viii | 2.6337 | H22P···H16viii | 2.5295 |
H1B···H5A | 2.2569 | H22P···H11P | 2.4383 |
H1N···C13 | 2.329 (19) | H22P···H31P | 2.2940 |
H1N···N | 2.443 (18) | H31P···H11Ax | 2.3331 |
H1N···C18 | 2.88 (2) | H31P···H11P | 2.5243 |
H1N···H2N | 2.58 (3) | H31P···H22P | 2.2940 |
H1N···C14 | 2.623 (19) | H32P···O3 | 2.7391 |
H1W···C7 | 2.91 (3) | H32P···C5 | 2.6113 |
H1W···H14v | 2.58 (3) | H32P···C9 | 3.0074 |
H1W···O1 | 1.99 (3) | H32P···H5PB | 2.1645 |
H4PB···H21P | 2.2976 | H32P···H10Aiv | 2.4473 |
H4PB···C2P | 2.9546 | | |
| | | |
H1W—O1W—H2W | 103 (3) | C5—C2—H2B | 108.34 |
C1—N—C2 | 113.1 (2) | N—C2—H2B | 108.33 |
C1—N—C3 | 107.24 (17) | H21P—C2P—H22P | 107.43 |
C1P—N—C2P | 110.9 (2) | C5—C2P—H21P | 108.39 |
C1P—N—C3P | 112.8 (2) | C5—C2P—H22P | 108.38 |
C2—N—C3 | 112.20 (18) | N—C2P—H22P | 108.39 |
C2P—N—C3P | 106.09 (18) | N—C2P—H21P | 108.49 |
C4—N1—C7 | 125.12 (14) | C6—C3—H3B | 108.45 |
C5—N2—C8 | 125.17 (13) | H3A—C3—H3B | 107.50 |
C6—N3—C9 | 123.84 (13) | N—C3—H3A | 108.42 |
C4—N1—H1N | 116.1 (12) | C6—C3—H3A | 108.43 |
C7—N1—H1N | 117.2 (12) | N—C3—H3B | 108.46 |
C8—N2—H2N | 119.8 (12) | C6—C3P—H32P | 108.38 |
C5—N2—H2N | 114.8 (12) | C6—C3P—H31P | 108.40 |
C6—N3—H3N | 118.1 (13) | H31P—C3P—H32P | 107.53 |
C9—N3—H3N | 118.0 (13) | N—C3P—H31P | 108.33 |
N—C1—C4 | 116.4 (2) | N—C3P—H32P | 108.38 |
N—C1P—C4 | 114.5 (3) | C1—C4—H4A | 109.46 |
N—C2—C5 | 115.8 (2) | N1—C4—H4A | 109.50 |
N—C2P—C5 | 115.5 (3) | N1—C4—H4B | 109.47 |
N—C3—C6 | 115.32 (19) | N1—C4—H4PA | 109.52 |
N—C3P—C6 | 115.5 (2) | C1—C4—H4B | 109.47 |
N1—C4—C1 | 110.84 (17) | H4A—C4—H4B | 108.05 |
N1—C4—C1P | 110.71 (19) | C1P—C4—H4PA | 109.51 |
N2—C5—C2P | 112.47 (16) | C1P—C4—H4PB | 109.49 |
N2—C5—C2 | 109.97 (15) | H4PA—C4—H4PB | 108.08 |
N3—C6—C3 | 112.96 (16) | N1—C4—H4PB | 109.48 |
N3—C6—C3P | 115.30 (15) | N2—C5—H5B | 109.64 |
O1—C7—C10 | 120.77 (13) | N2—C5—H5PA | 109.11 |
N1—C7—C10 | 117.22 (14) | N2—C5—H5A | 109.64 |
O1—C7—N1 | 121.98 (15) | C2—C5—H5A | 109.65 |
O2—C8—C11 | 120.56 (13) | C2—C5—H5B | 109.67 |
O2—C8—N2 | 122.18 (14) | H5A—C5—H5B | 108.25 |
N2—C8—C11 | 117.27 (12) | C2P—C5—H5PA | 109.09 |
N3—C9—C12 | 115.90 (13) | C2P—C5—H5PB | 109.12 |
O3—C9—C12 | 121.69 (14) | H5PA—C5—H5PB | 107.88 |
O3—C9—N3 | 122.34 (14) | N2—C5—H5PB | 109.06 |
C7—C10—C13 | 114.72 (12) | N3—C6—H6A | 108.99 |
C8—C11—C15 | 113.89 (12) | N3—C6—H6B | 109.00 |
C9—C12—C17 | 107.57 (12) | N3—C6—H6PA | 108.45 |
C14—C13—C18 | 118.77 (13) | N3—C6—H6PB | 108.45 |
C10—C13—C18 | 119.73 (12) | C3—C6—H6A | 109.02 |
C10—C13—C14 | 120.68 (13) | C3—C6—H6B | 108.97 |
C13—C14—C15 | 120.99 (14) | H6A—C6—H6B | 107.77 |
C14—C15—C16 | 118.76 (13) | C3P—C6—H6PA | 108.43 |
C11—C15—C16 | 119.12 (13) | C3P—C6—H6PB | 108.46 |
C11—C15—C14 | 121.10 (13) | H6PA—C6—H6PB | 107.50 |
C15—C16—C17 | 121.10 (14) | C7—C10—H10A | 108.59 |
C12—C17—C16 | 119.33 (13) | C7—C10—H10B | 108.55 |
C12—C17—C18 | 120.50 (12) | C13—C10—H10A | 108.58 |
C16—C17—C18 | 119.13 (13) | C13—C10—H10B | 108.63 |
C13—C18—C17 | 121.13 (13) | H10A—C10—H10B | 107.54 |
C10—C13—C16 | 171.00 (10) | C8—C11—H11B | 108.81 |
C11—C15—C18 | 168.92 (10) | C15—C11—H11A | 108.82 |
C12—C17—C14 | 167.97 (10) | C15—C11—H11B | 108.75 |
N—C1—H1B | 108.25 | H11A—C11—H11B | 107.62 |
C4—C1—H1A | 108.18 | C8—C11—H11A | 108.78 |
N—C1—H1A | 108.20 | C9—C12—H12A | 110.15 |
H1A—C1—H1B | 107.31 | C17—C12—H12A | 110.20 |
C4—C1—H1B | 108.12 | C17—C12—H12B | 110.22 |
C4—C1P—H12P | 108.56 | C9—C12—H12B | 110.18 |
H11P—C1P—H12P | 107.64 | H12A—C12—H12B | 108.51 |
C4—C1P—H11P | 108.58 | C15—C14—H14 | 120.9 (9) |
N—C1P—H11P | 108.69 | C13—C14—H14 | 117.8 (9) |
N—C1P—H12P | 108.70 | C15—C16—H16 | 119.8 (9) |
H2A—C2—H2B | 107.41 | C17—C16—H16 | 119.0 (9) |
N—C2—H2A | 108.33 | C13—C18—H18 | 118.9 (9) |
C5—C2—H2A | 108.32 | C17—C18—H18 | 119.8 (9) |
| | | |
C2—N—C1—C4 | 165.4 (2) | N—C1—C4—N1 | −46.8 (3) |
C3—N—C1—C4 | −70.3 (2) | N—C2—C5—N2 | −48.0 (3) |
C1—N—C2—C5 | −70.1 (3) | N—C3—C6—N3 | −62.6 (2) |
C3—N—C2—C5 | 168.4 (2) | N1—C7—C10—C13 | 10.2 (2) |
C1—N—C3—C6 | 170.93 (19) | O1—C7—C10—C13 | −171.80 (14) |
C2—N—C3—C6 | −64.2 (3) | N2—C8—C11—C15 | −1.4 (2) |
C7—N1—C4—C1 | 178.50 (18) | O2—C8—C11—C15 | 179.11 (14) |
C4—N1—C7—O1 | 6.4 (3) | N3—C9—C12—C17 | 70.72 (16) |
C4—N1—C7—C10 | −175.59 (14) | O3—C9—C12—C17 | −106.26 (16) |
C8—N2—C5—C2 | −170.7 (2) | C7—C10—C13—C14 | −82.12 (17) |
C5—N2—C8—O2 | 4.8 (3) | C7—C10—C13—C18 | 87.39 (16) |
C5—N2—C8—C11 | −174.66 (15) | C8—C11—C15—C14 | 92.19 (16) |
C9—N3—C6—C3 | 126.16 (18) | C8—C11—C15—C16 | −76.12 (18) |
C6—N3—C9—O3 | 2.6 (2) | C9—C12—C17—C16 | 74.19 (17) |
C6—N3—C9—C12 | −174.34 (13) | C9—C12—C17—C18 | −94.07 (15) |
C1—N—C2—H2A | 168.07 | C18—C13—C14—C15 | −0.9 (2) |
C1—N—C2—H2B | 51.85 | C10—C13—C14—C15 | 168.67 (13) |
C3—N—C2—H2A | 46.57 | C10—C13—C18—C17 | −168.07 (13) |
C3—N—C2—H2B | −69.65 | C14—C13—C18—C17 | 1.6 (2) |
C1—N—C3—H3A | −67.32 | C13—C14—C15—C11 | −166.64 (13) |
C1—N—C3—H3B | 49.12 | C13—C14—C15—C16 | 1.7 (2) |
C2—N—C3—H3A | 57.50 | C14—C15—C16—C17 | −3.2 (2) |
C2—N—C3—H3B | 173.94 | C11—C15—C16—C17 | 165.38 (13) |
C3—N—C1—H1B | 167.68 | C15—C16—C17—C12 | −164.54 (13) |
C2—N—C1—H1A | −72.56 | C15—C16—C17—C18 | 3.9 (2) |
C2—N—C1—H1B | 43.42 | C16—C17—C18—C13 | −3.1 (2) |
C3—N—C1—H1A | 51.69 | C12—C17—C18—C13 | 165.20 (13) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+3/2, z+1/2; (v) −x+1, −y+2, −z; (vi) −x+1/2, y+1/2, −z−1/2; (vii) x−1/2, −y+3/2, z−1/2; (viii) −x+1/2, y+1/2, −z+1/2; (ix) −x, −y+1, −z; (x) x−1, y, z; (xi) x+1, y, z; (xii) −x, −y+2, −z; (xiii) −x+1/2, y−1/2, −z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N | 0.85 (2) | 2.443 (18) | 2.8240 (18) | 108.2 (14) |
O1W—H1W···O1 | 0.85 (3) | 1.99 (3) | 2.834 (2) | 173 (3) |
N2—H2N···N | 0.870 (18) | 2.451 (18) | 2.8593 (17) | 109.4 (14) |
O1W—H2W···O3i | 0.93 (5) | 2.09 (5) | 2.940 (2) | 151 (4) |
N3—H3N···O2vii | 0.84 (2) | 2.168 (19) | 2.9540 (18) | 156.3 (17) |
C5—H5A···O3viii | 0.97 | 2.52 | 3.465 (2) | 165 |
C6—H6A···O3 | 0.97 | 2.40 | 2.799 (2) | 104 |
C12—H12B···O1Wxiii | 0.97 | 2.55 | 3.504 (2) | 167 |
C14—H14···O1v | 0.975 (16) | 2.525 (16) | 3.438 (2) | 155.9 (13) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (v) −x+1, −y+2, −z; (vii) x−1/2, −y+3/2, z−1/2; (viii) −x+1/2, y+1/2, −z+1/2; (xiii) −x+1/2, y−1/2, −z−1/2. |