Buy article online - an online subscription or single-article purchase is required to access this article.
The structures of the cocrystalline adducts of 3-nitrophenol (3-NP) with 1,3,5,7-tetraazatricyclo[3.3.1.1
3,7]decane [HMTA, (
1)] as the 2:1:1 hydrate, 2C
6H
5NO
3·C
6H
12N
4·H
2O, (
1a), with 1,3,6,8-tetraazatricyclo[4.3.1.1
3,8]undecane [TATU (
2)] as the 2:1 cocrystal, 2C
6H
5NO
3·C
7H
14N
4, (
2a), and with 1,3,6,8-tetraazatricyclo[4.4.1.1
3,8]dodecane [TATD, (
3)] as the 2:1 cocrystal, 2C
6H
5NO
3·C
8H
16N
4, (
3a), are reported. In the binary crystals (
2a) and (
3a), the 3-nitrophenol molecules are linked
via O—H
N hydrogen bonds into aminal cage azaadamantanes. In (
1a), the structure is stabilized by O—H
N and O—H
O hydrogen bonds, and generates ternary cocrystals. There are C—H
O hydrogen bonds present in all three cocrystals, and in (
1a), there are also C—H
O and C—H
π interactions present. The presence of an ethylene bridge in the structures of (
2) and (
3) defines the formation of a hydrogen-bonded motif in the supramolecular architectures of (
2a) and (
3a). The differences in the C—N bond lengths of the aminal cage structures, as a result of hyperconjugative interactions and electron delocalization, were analysed. These three cocrystals were obtained by the solvent-free assisted grinding method. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation from a mixture of hexanes.
Supporting information
CCDC references: 1868031; 1964999; 1964998
For all structures, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015) for (1a), (2a); SHELXL2014 (Sheldrick, 2015) for (3a). For all structures, molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008). Software used to prepare material for publication: SHELXL for (1a), (3a); SHELXL2018 (Sheldrick, 2015) for (2a).
3-Nitrophenol–1,3,5,7-tetraazatricyclo[3.3.1.1
3,7]decane–water (2:1:1) (1a)
top
Crystal data top
2C6H5NO3·C6H12N4·H2O | F(000) = 920 |
Mr = 436.43 | Dx = 1.427 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6765 (6) Å | Cell parameters from 8615 reflections |
b = 28.819 (3) Å | θ = 2.4–25.5° |
c = 6.8163 (4) Å | µ = 0.11 mm−1 |
β = 104.395 (5)° | T = 173 K |
V = 2031.5 (2) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.25 × 0.23 mm |
Data collection top
Stoe IPDS II two-circle diffractometer | 3024 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.030 |
ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −12→12 |
Tmin = 0.678, Tmax = 1.000 | k = −32→34 |
8615 measured reflections | l = −8→8 |
3559 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0402P)2 + 1.5429P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.136 | (Δ/σ)max < 0.001 |
S = 1.24 | Δρmax = 0.19 e Å−3 |
3559 reflections | Δρmin = −0.19 e Å−3 |
297 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0076 (14) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.5573 (2) | 0.67919 (7) | 0.7511 (4) | 0.0366 (5) | |
N2 | 0.4781 (2) | 0.60884 (7) | 0.5599 (3) | 0.0327 (5) | |
N3 | 0.33305 (19) | 0.65519 (7) | 0.7072 (3) | 0.0332 (5) | |
N4 | 0.5062 (2) | 0.61043 (7) | 0.9282 (3) | 0.0331 (5) | |
C1 | 0.5915 (3) | 0.65086 (10) | 0.9378 (4) | 0.0401 (7) | |
H1A | 0.681983 | 0.640054 | 0.959915 | 0.048* | |
H1B | 0.586100 | 0.670411 | 1.054823 | 0.048* | |
C2 | 0.5156 (3) | 0.58242 (9) | 0.7514 (4) | 0.0322 (6) | |
H2A | 0.458936 | 0.554902 | 0.741831 | 0.039* | |
H2B | 0.605653 | 0.571291 | 0.771096 | 0.039* | |
C3 | 0.3720 (2) | 0.62791 (9) | 0.8928 (4) | 0.0359 (6) | |
H3A | 0.312399 | 0.601265 | 0.884507 | 0.043* | |
H3B | 0.364706 | 0.647336 | 1.009225 | 0.043* | |
C4 | 0.5646 (3) | 0.64920 (10) | 0.5797 (4) | 0.0382 (7) | |
H4A | 0.541298 | 0.667554 | 0.453018 | 0.046* | |
H4B | 0.654635 | 0.638251 | 0.598163 | 0.046* | |
C5 | 0.4215 (2) | 0.69446 (9) | 0.7219 (5) | 0.0373 (6) | |
H5A | 0.414552 | 0.714399 | 0.836998 | 0.045* | |
H5B | 0.395893 | 0.713233 | 0.596619 | 0.045* | |
C6 | 0.3447 (3) | 0.62584 (10) | 0.5374 (4) | 0.0384 (7) | |
H6A | 0.317536 | 0.643770 | 0.410031 | 0.046* | |
H6B | 0.285698 | 0.598956 | 0.527655 | 0.046* | |
O1 | 0.67092 (17) | 0.76454 (7) | 0.7865 (3) | 0.0385 (5) | |
H1 | 0.651 (3) | 0.7352 (13) | 0.787 (5) | 0.055 (10)* | |
N11 | 1.1070 (2) | 0.70433 (8) | 1.0448 (3) | 0.0353 (5) | |
O11 | 1.0675 (2) | 0.66478 (7) | 1.0085 (4) | 0.0513 (6) | |
O12 | 1.22130 (18) | 0.71336 (7) | 1.1252 (4) | 0.0513 (6) | |
C11 | 0.8000 (2) | 0.76995 (9) | 0.8651 (4) | 0.0285 (5) | |
C12 | 0.8856 (2) | 0.73314 (8) | 0.9132 (4) | 0.0286 (5) | |
H12 | 0.856114 | 0.701995 | 0.892213 | 0.034* | |
C13 | 1.0151 (2) | 0.74298 (9) | 0.9928 (4) | 0.0290 (6) | |
C14 | 1.0635 (2) | 0.78777 (9) | 1.0261 (4) | 0.0338 (6) | |
H14 | 1.152891 | 0.793388 | 1.082108 | 0.041* | |
C15 | 0.9763 (3) | 0.82382 (9) | 0.9747 (4) | 0.0346 (6) | |
H15 | 1.006319 | 0.854908 | 0.994883 | 0.042* | |
C16 | 0.8464 (2) | 0.81552 (9) | 0.8945 (4) | 0.0322 (6) | |
H16 | 0.788122 | 0.840830 | 0.859155 | 0.039* | |
O2 | 0.7877 (2) | 0.50228 (8) | 0.3853 (3) | 0.0440 (5) | |
H2 | 0.716 (4) | 0.5208 (14) | 0.345 (6) | 0.072 (12)* | |
C21 | 0.8154 (2) | 0.48511 (9) | 0.2156 (4) | 0.0318 (6) | |
N21 | 1.0827 (2) | 0.41888 (8) | 0.0861 (4) | 0.0424 (6) | |
O21 | 1.1452 (2) | 0.40915 (8) | 0.2579 (4) | 0.0583 (6) | |
O22 | 1.1177 (2) | 0.40958 (8) | −0.0674 (4) | 0.0554 (6) | |
C22 | 0.9311 (2) | 0.46097 (9) | 0.2370 (4) | 0.0336 (6) | |
H22 | 0.988755 | 0.456605 | 0.366383 | 0.040* | |
C23 | 0.9595 (2) | 0.44357 (8) | 0.0639 (4) | 0.0329 (6) | |
C24 | 0.8798 (3) | 0.44897 (9) | −0.1276 (4) | 0.0354 (6) | |
H24 | 0.902966 | 0.436865 | −0.243325 | 0.043* | |
C25 | 0.7648 (3) | 0.47265 (9) | −0.1451 (4) | 0.0356 (6) | |
H25 | 0.707599 | 0.476886 | −0.274972 | 0.043* | |
C26 | 0.7322 (2) | 0.49024 (8) | 0.0246 (4) | 0.0314 (6) | |
H26 | 0.652246 | 0.505971 | 0.010350 | 0.038* | |
O1W | 0.5718 (2) | 0.55333 (8) | 0.2806 (3) | 0.0446 (5) | |
H1WA | 0.536 (5) | 0.5697 (17) | 0.356 (8) | 0.104 (17)* | |
H1WB | 0.558 (4) | 0.5722 (16) | 0.165 (8) | 0.098 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0253 (11) | 0.0278 (11) | 0.0552 (15) | 0.0004 (9) | 0.0070 (10) | 0.0017 (10) |
N2 | 0.0364 (12) | 0.0321 (12) | 0.0299 (12) | 0.0056 (9) | 0.0087 (9) | 0.0007 (9) |
N3 | 0.0241 (11) | 0.0283 (11) | 0.0467 (13) | 0.0025 (9) | 0.0075 (9) | 0.0030 (10) |
N4 | 0.0338 (12) | 0.0310 (11) | 0.0350 (12) | 0.0066 (9) | 0.0094 (9) | 0.0021 (9) |
C1 | 0.0293 (13) | 0.0375 (15) | 0.0474 (17) | 0.0020 (11) | −0.0017 (12) | −0.0074 (13) |
C2 | 0.0349 (14) | 0.0260 (13) | 0.0361 (14) | 0.0038 (11) | 0.0095 (11) | 0.0015 (11) |
C3 | 0.0336 (14) | 0.0325 (14) | 0.0448 (16) | 0.0028 (11) | 0.0157 (12) | 0.0005 (12) |
C4 | 0.0348 (14) | 0.0378 (15) | 0.0471 (17) | 0.0044 (12) | 0.0196 (12) | 0.0100 (13) |
C5 | 0.0292 (14) | 0.0248 (13) | 0.0578 (18) | 0.0036 (11) | 0.0107 (12) | 0.0028 (12) |
C6 | 0.0310 (14) | 0.0368 (14) | 0.0419 (16) | 0.0005 (11) | −0.0014 (11) | −0.0006 (12) |
O1 | 0.0287 (10) | 0.0300 (10) | 0.0527 (12) | −0.0047 (8) | 0.0023 (8) | 0.0034 (9) |
N11 | 0.0332 (12) | 0.0336 (12) | 0.0403 (13) | −0.0012 (10) | 0.0117 (10) | −0.0003 (10) |
O11 | 0.0469 (12) | 0.0291 (11) | 0.0753 (16) | 0.0001 (9) | 0.0103 (11) | −0.0006 (10) |
O12 | 0.0274 (10) | 0.0466 (12) | 0.0761 (16) | 0.0010 (9) | 0.0058 (10) | −0.0008 (11) |
C11 | 0.0275 (13) | 0.0297 (13) | 0.0297 (13) | −0.0043 (10) | 0.0097 (10) | −0.0011 (10) |
C12 | 0.0333 (13) | 0.0258 (12) | 0.0282 (13) | −0.0069 (10) | 0.0104 (10) | −0.0009 (10) |
C13 | 0.0276 (13) | 0.0287 (13) | 0.0322 (14) | −0.0009 (10) | 0.0106 (10) | −0.0005 (10) |
C14 | 0.0281 (13) | 0.0341 (14) | 0.0393 (15) | −0.0064 (11) | 0.0088 (11) | −0.0038 (11) |
C15 | 0.0381 (15) | 0.0276 (13) | 0.0404 (15) | −0.0078 (11) | 0.0140 (12) | −0.0045 (11) |
C16 | 0.0354 (14) | 0.0268 (13) | 0.0366 (15) | −0.0021 (11) | 0.0132 (11) | −0.0007 (11) |
O2 | 0.0449 (12) | 0.0533 (13) | 0.0325 (11) | 0.0168 (10) | 0.0074 (9) | 0.0002 (9) |
C21 | 0.0325 (13) | 0.0279 (13) | 0.0352 (14) | 0.0011 (11) | 0.0089 (11) | 0.0008 (11) |
N21 | 0.0312 (12) | 0.0274 (12) | 0.0700 (18) | −0.0008 (10) | 0.0149 (13) | −0.0004 (12) |
O21 | 0.0364 (11) | 0.0552 (14) | 0.0786 (17) | 0.0150 (10) | 0.0055 (11) | 0.0075 (12) |
O22 | 0.0455 (12) | 0.0463 (13) | 0.0844 (17) | 0.0045 (10) | 0.0347 (12) | −0.0059 (12) |
C22 | 0.0289 (13) | 0.0288 (13) | 0.0407 (15) | −0.0018 (11) | 0.0042 (11) | 0.0039 (11) |
C23 | 0.0277 (13) | 0.0214 (12) | 0.0510 (17) | −0.0010 (10) | 0.0124 (11) | 0.0000 (11) |
C24 | 0.0377 (14) | 0.0300 (14) | 0.0405 (15) | −0.0017 (11) | 0.0134 (12) | −0.0047 (11) |
C25 | 0.0359 (14) | 0.0329 (14) | 0.0364 (15) | −0.0009 (11) | 0.0057 (11) | 0.0006 (11) |
C26 | 0.0294 (13) | 0.0261 (13) | 0.0383 (15) | 0.0038 (10) | 0.0074 (11) | 0.0036 (11) |
O1W | 0.0502 (12) | 0.0507 (13) | 0.0350 (11) | 0.0204 (10) | 0.0147 (10) | 0.0040 (10) |
Geometric parameters (Å, º) top
N1—C4 | 1.471 (4) | N11—C13 | 1.469 (3) |
N1—C1 | 1.479 (4) | C11—C12 | 1.385 (4) |
N1—C5 | 1.481 (3) | C11—C16 | 1.400 (4) |
N2—C4 | 1.470 (3) | C12—C13 | 1.383 (3) |
N2—C2 | 1.478 (3) | C12—H12 | 0.9500 |
N2—C6 | 1.478 (3) | C13—C14 | 1.388 (4) |
N3—C3 | 1.459 (3) | C14—C15 | 1.381 (4) |
N3—C5 | 1.461 (3) | C14—H14 | 0.9500 |
N3—C6 | 1.464 (4) | C15—C16 | 1.379 (4) |
N4—C1 | 1.470 (4) | C15—H15 | 0.9500 |
N4—C2 | 1.474 (3) | C16—H16 | 0.9500 |
N4—C3 | 1.481 (3) | O2—C21 | 1.357 (3) |
C1—H1A | 0.9900 | O2—H2 | 0.92 (4) |
C1—H1B | 0.9900 | C21—C26 | 1.389 (4) |
C2—H2A | 0.9900 | C21—C22 | 1.394 (4) |
C2—H2B | 0.9900 | N21—O22 | 1.225 (3) |
C3—H3A | 0.9900 | N21—O21 | 1.227 (3) |
C3—H3B | 0.9900 | N21—C23 | 1.470 (3) |
C4—H4A | 0.9900 | C22—C23 | 1.383 (4) |
C4—H4B | 0.9900 | C22—H22 | 0.9500 |
C5—H5A | 0.9900 | C23—C24 | 1.378 (4) |
C5—H5B | 0.9900 | C24—C25 | 1.384 (4) |
C6—H6A | 0.9900 | C24—H24 | 0.9500 |
C6—H6B | 0.9900 | C25—C26 | 1.384 (4) |
O1—C11 | 1.358 (3) | C25—H25 | 0.9500 |
O1—H1 | 0.87 (4) | C26—H26 | 0.9500 |
N11—O11 | 1.219 (3) | O1W—H1WA | 0.85 (5) |
N11—O12 | 1.234 (3) | O1W—H1WB | 0.94 (5) |
| | | |
C4—N1—C1 | 108.0 (2) | H6A—C6—H6B | 107.9 |
C4—N1—C5 | 108.1 (2) | C11—O1—H1 | 109 (2) |
C1—N1—C5 | 107.7 (2) | O11—N11—O12 | 122.8 (2) |
C4—N2—C2 | 107.5 (2) | O11—N11—C13 | 118.9 (2) |
C4—N2—C6 | 108.3 (2) | O12—N11—C13 | 118.3 (2) |
C2—N2—C6 | 107.8 (2) | O1—C11—C12 | 123.4 (2) |
C3—N3—C5 | 108.5 (2) | O1—C11—C16 | 116.9 (2) |
C3—N3—C6 | 108.2 (2) | C12—C11—C16 | 119.7 (2) |
C5—N3—C6 | 108.7 (2) | C13—C12—C11 | 118.1 (2) |
C1—N4—C2 | 107.7 (2) | C13—C12—H12 | 120.9 |
C1—N4—C3 | 107.5 (2) | C11—C12—H12 | 120.9 |
C2—N4—C3 | 108.2 (2) | C12—C13—C14 | 123.4 (2) |
N4—C1—N1 | 112.4 (2) | C12—C13—N11 | 118.8 (2) |
N4—C1—H1A | 109.1 | C14—C13—N11 | 117.8 (2) |
N1—C1—H1A | 109.1 | C15—C14—C13 | 117.3 (2) |
N4—C1—H1B | 109.1 | C15—C14—H14 | 121.4 |
N1—C1—H1B | 109.1 | C13—C14—H14 | 121.4 |
H1A—C1—H1B | 107.9 | C16—C15—C14 | 121.2 (2) |
N4—C2—N2 | 112.4 (2) | C16—C15—H15 | 119.4 |
N4—C2—H2A | 109.1 | C14—C15—H15 | 119.4 |
N2—C2—H2A | 109.1 | C15—C16—C11 | 120.3 (2) |
N4—C2—H2B | 109.1 | C15—C16—H16 | 119.9 |
N2—C2—H2B | 109.1 | C11—C16—H16 | 119.9 |
H2A—C2—H2B | 107.9 | C21—O2—H2 | 107 (2) |
N3—C3—N4 | 112.3 (2) | O2—C21—C26 | 122.4 (2) |
N3—C3—H3A | 109.1 | O2—C21—C22 | 117.9 (2) |
N4—C3—H3A | 109.1 | C26—C21—C22 | 119.7 (2) |
N3—C3—H3B | 109.1 | O22—N21—O21 | 123.8 (3) |
N4—C3—H3B | 109.1 | O22—N21—C23 | 118.2 (3) |
H3A—C3—H3B | 107.9 | O21—N21—C23 | 118.0 (3) |
N2—C4—N1 | 112.5 (2) | C23—C22—C21 | 117.9 (2) |
N2—C4—H4A | 109.1 | C23—C22—H22 | 121.0 |
N1—C4—H4A | 109.1 | C21—C22—H22 | 121.0 |
N2—C4—H4B | 109.1 | C24—C23—C22 | 123.5 (2) |
N1—C4—H4B | 109.1 | C24—C23—N21 | 118.6 (3) |
H4A—C4—H4B | 107.8 | C22—C23—N21 | 117.9 (2) |
N3—C5—N1 | 111.9 (2) | C23—C24—C25 | 117.6 (3) |
N3—C5—H5A | 109.2 | C23—C24—H24 | 121.2 |
N1—C5—H5A | 109.2 | C25—C24—H24 | 121.2 |
N3—C5—H5B | 109.2 | C24—C25—C26 | 120.7 (2) |
N1—C5—H5B | 109.2 | C24—C25—H25 | 119.7 |
H5A—C5—H5B | 107.9 | C26—C25—H25 | 119.7 |
N3—C6—N2 | 112.2 (2) | C25—C26—C21 | 120.6 (2) |
N3—C6—H6A | 109.2 | C25—C26—H26 | 119.7 |
N2—C6—H6A | 109.2 | C21—C26—H26 | 119.7 |
N3—C6—H6B | 109.2 | H1WA—O1W—H1WB | 101 (4) |
N2—C6—H6B | 109.2 | | |
| | | |
C2—N4—C1—N1 | 58.2 (3) | C11—C12—C13—C14 | −0.2 (4) |
C3—N4—C1—N1 | −58.2 (3) | C11—C12—C13—N11 | 179.9 (2) |
C4—N1—C1—N4 | −58.1 (3) | O11—N11—C13—C12 | 3.1 (4) |
C5—N1—C1—N4 | 58.4 (3) | O12—N11—C13—C12 | −176.4 (2) |
C1—N4—C2—N2 | −58.9 (3) | O11—N11—C13—C14 | −176.8 (2) |
C3—N4—C2—N2 | 57.1 (3) | O12—N11—C13—C14 | 3.7 (4) |
C4—N2—C2—N4 | 59.0 (3) | C12—C13—C14—C15 | −0.5 (4) |
C6—N2—C2—N4 | −57.5 (3) | N11—C13—C14—C15 | 179.4 (2) |
C5—N3—C3—N4 | −59.0 (3) | C13—C14—C15—C16 | 0.4 (4) |
C6—N3—C3—N4 | 58.8 (3) | C14—C15—C16—C11 | 0.5 (4) |
C1—N4—C3—N3 | 58.3 (3) | O1—C11—C16—C15 | 179.7 (2) |
C2—N4—C3—N3 | −57.7 (3) | C12—C11—C16—C15 | −1.2 (4) |
C2—N2—C4—N1 | −58.7 (3) | O2—C21—C22—C23 | −179.8 (2) |
C6—N2—C4—N1 | 57.4 (3) | C26—C21—C22—C23 | 1.0 (4) |
C1—N1—C4—N2 | 58.4 (3) | C21—C22—C23—C24 | 0.2 (4) |
C5—N1—C4—N2 | −57.9 (3) | C21—C22—C23—N21 | 178.9 (2) |
C3—N3—C5—N1 | 58.9 (3) | O22—N21—C23—C24 | 9.7 (3) |
C6—N3—C5—N1 | −58.6 (3) | O21—N21—C23—C24 | −171.0 (2) |
C4—N1—C5—N3 | 58.2 (3) | O22—N21—C23—C22 | −169.1 (2) |
C1—N1—C5—N3 | −58.2 (3) | O21—N21—C23—C22 | 10.2 (3) |
C3—N3—C6—N2 | −59.5 (3) | C22—C23—C24—C25 | −0.8 (4) |
C5—N3—C6—N2 | 58.2 (3) | N21—C23—C24—C25 | −179.5 (2) |
C4—N2—C6—N3 | −57.3 (3) | C23—C24—C25—C26 | 0.2 (4) |
C2—N2—C6—N3 | 58.7 (3) | C24—C25—C26—C21 | 1.1 (4) |
O1—C11—C12—C13 | −179.9 (2) | O2—C21—C26—C25 | 179.2 (2) |
C16—C11—C12—C13 | 1.0 (4) | C22—C21—C26—C25 | −1.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.87 (4) | 1.89 (4) | 2.727 (3) | 162 (3) |
O2—H2···O1W | 0.92 (4) | 1.76 (4) | 2.677 (3) | 175 (4) |
O1W—H1WA···N2 | 0.85 (5) | 2.00 (5) | 2.852 (3) | 172 (5) |
O1W—H1WB···N4i | 0.94 (5) | 1.92 (5) | 2.852 (3) | 173 (4) |
C1—H1A···O22ii | 0.99 | 2.53 | 3.476 (3) | 161 |
C1—H1B···O1iii | 0.99 | 2.47 | 3.363 (3) | 149 |
C4—H4B···O21ii | 0.99 | 2.52 | 3.457 (3) | 158 |
C14—H14···N3iv | 0.95 | 2.41 | 3.278 (3) | 152 |
Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y+1, −z+1; (iii) x, −y+3/2, z+1/2; (iv) x+1, −y+3/2, z+1/2. |
3-Nitrophenol–1,3,6,8-tetraazatricyclo[4.3.1.1
3,8]undecane (2:1) (2a)
top
Crystal data top
C7H14N4·2C6H5NO3 | F(000) = 456 |
Mr = 432.44 | Dx = 1.413 Mg m−3 |
Monoclinic, Cm | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2053 (7) Å | Cell parameters from 8351 reflections |
b = 25.253 (2) Å | θ = 3.4–27.8° |
c = 6.5134 (6) Å | µ = 0.11 mm−1 |
β = 120.939 (6)° | T = 173 K |
V = 1016.52 (17) Å3 | Plate, yellow |
Z = 2 | 0.23 × 0.17 × 0.08 mm |
Data collection top
Stoe IPDS II two-circle diffractometer | 2119 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.036 |
ω scans | θmax = 27.6°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.529, Tmax = 1.000 | k = −32→32 |
8351 measured reflections | l = −8→8 |
2401 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.17 e Å−3 |
2401 reflections | Δρmin = −0.19 e Å−3 |
149 parameters | Absolute structure: Flack x determined using 883 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
2 restraints | Absolute structure parameter: −1.8 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5286 (3) | 0.16364 (8) | 0.7582 (3) | 0.0347 (5) | |
H1 | 0.530 (6) | 0.1304 (15) | 0.718 (6) | 0.042 (9)* | |
O2 | 0.5119 (4) | 0.37561 (9) | 0.3797 (4) | 0.0585 (7) | |
O3 | 0.5330 (4) | 0.35709 (9) | 0.7134 (4) | 0.0495 (6) | |
N1 | 0.5539 (4) | 0.05764 (9) | 0.7291 (4) | 0.0322 (5) | |
N2 | 0.8694 (6) | 0.000000 | 1.0000 (6) | 0.0405 (8) | |
N3 | 0.5526 (6) | 0.000000 | 1.0384 (6) | 0.0380 (8) | |
N11 | 0.5176 (4) | 0.34371 (9) | 0.5246 (4) | 0.0361 (6) | |
C1 | 0.7924 (5) | 0.04855 (11) | 0.8566 (6) | 0.0392 (7) | |
H1A | 0.837407 | 0.047695 | 0.736394 | 0.047* | |
H1B | 0.865436 | 0.079135 | 0.963243 | 0.047* | |
C2 | 0.4302 (6) | 0.03087 (11) | 0.4979 (5) | 0.0403 (7) | |
H2A | 0.486413 | 0.042928 | 0.395508 | 0.048* | |
H2B | 0.278114 | 0.042929 | 0.421294 | 0.048* | |
C3 | 0.4749 (5) | 0.04851 (11) | 0.8952 (5) | 0.0376 (7) | |
H3A | 0.517924 | 0.079087 | 1.005633 | 0.045* | |
H3B | 0.314779 | 0.047512 | 0.801087 | 0.045* | |
C4 | 0.7891 (8) | 0.000000 | 1.1659 (7) | 0.0430 (10) | |
H4A | 0.844458 | −0.031708 | 1.269749 | 0.052* | 0.5 |
H4B | 0.844459 | 0.031708 | 1.269750 | 0.052* | 0.5 |
C11 | 0.5156 (4) | 0.19734 (10) | 0.5904 (4) | 0.0246 (5) | |
C12 | 0.5266 (4) | 0.25136 (11) | 0.6409 (4) | 0.0258 (5) | |
H12 | 0.546383 | 0.263450 | 0.788997 | 0.031* | |
C13 | 0.5077 (4) | 0.28686 (10) | 0.4689 (4) | 0.0267 (5) | |
C14 | 0.4793 (4) | 0.27170 (11) | 0.2496 (4) | 0.0301 (6) | |
H14 | 0.466071 | 0.297122 | 0.135315 | 0.036* | |
C15 | 0.4711 (4) | 0.21778 (11) | 0.2049 (4) | 0.0298 (5) | |
H15 | 0.453845 | 0.205983 | 0.057549 | 0.036* | |
C16 | 0.4876 (4) | 0.18075 (10) | 0.3706 (4) | 0.0276 (5) | |
H16 | 0.479787 | 0.144038 | 0.335216 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0577 (13) | 0.0219 (9) | 0.0310 (9) | 0.0006 (9) | 0.0274 (9) | 0.0025 (7) |
O2 | 0.0795 (19) | 0.0290 (12) | 0.0552 (14) | −0.0007 (11) | 0.0261 (13) | 0.0148 (10) |
O3 | 0.0660 (15) | 0.0305 (11) | 0.0626 (14) | −0.0020 (10) | 0.0405 (12) | −0.0109 (11) |
N1 | 0.0488 (14) | 0.0221 (10) | 0.0312 (11) | 0.0011 (10) | 0.0245 (10) | 0.0017 (9) |
N2 | 0.043 (2) | 0.0312 (17) | 0.0422 (19) | 0.000 | 0.0187 (16) | 0.000 |
N3 | 0.067 (2) | 0.0230 (15) | 0.0340 (16) | 0.000 | 0.0327 (17) | 0.000 |
N11 | 0.0346 (13) | 0.0232 (11) | 0.0461 (15) | 0.0018 (9) | 0.0175 (11) | 0.0030 (10) |
C1 | 0.0489 (17) | 0.0279 (14) | 0.0464 (16) | −0.0057 (12) | 0.0284 (14) | −0.0011 (11) |
C2 | 0.0609 (19) | 0.0271 (15) | 0.0302 (13) | 0.0047 (12) | 0.0215 (13) | 0.0031 (10) |
C3 | 0.059 (2) | 0.0246 (13) | 0.0409 (15) | 0.0027 (12) | 0.0343 (15) | 0.0000 (11) |
C4 | 0.066 (3) | 0.028 (2) | 0.0284 (18) | 0.000 | 0.0198 (19) | 0.000 |
C11 | 0.0256 (12) | 0.0249 (12) | 0.0232 (11) | 0.0006 (10) | 0.0123 (9) | 0.0015 (9) |
C12 | 0.0263 (12) | 0.0261 (12) | 0.0237 (11) | 0.0009 (10) | 0.0120 (9) | −0.0003 (9) |
C13 | 0.0249 (12) | 0.0230 (12) | 0.0289 (11) | 0.0010 (9) | 0.0114 (10) | 0.0015 (9) |
C14 | 0.0286 (13) | 0.0333 (13) | 0.0266 (12) | 0.0024 (11) | 0.0129 (10) | 0.0076 (10) |
C15 | 0.0275 (13) | 0.0381 (14) | 0.0234 (11) | 0.0004 (11) | 0.0127 (10) | −0.0002 (10) |
C16 | 0.0308 (13) | 0.0245 (12) | 0.0279 (12) | −0.0002 (10) | 0.0154 (11) | −0.0039 (10) |
Geometric parameters (Å, º) top
O1—C11 | 1.350 (3) | C2—H2A | 0.9900 |
O1—H1 | 0.88 (4) | C2—H2B | 0.9900 |
O2—N11 | 1.225 (3) | C3—H3A | 0.9900 |
O3—N11 | 1.224 (3) | C3—H3B | 0.9900 |
N1—C2 | 1.463 (4) | C4—H4A | 0.9900 |
N1—C3 | 1.477 (3) | C4—H4B | 0.9900 |
N1—C1 | 1.493 (4) | C11—C12 | 1.396 (3) |
N2—C4 | 1.465 (5) | C11—C16 | 1.403 (3) |
N2—C1i | 1.466 (3) | C12—C13 | 1.386 (3) |
N2—C1 | 1.466 (3) | C12—H12 | 0.9500 |
N3—C4 | 1.462 (6) | C13—C14 | 1.388 (4) |
N3—C3i | 1.465 (3) | C14—C15 | 1.387 (4) |
N3—C3 | 1.465 (3) | C14—H14 | 0.9500 |
N11—C13 | 1.474 (3) | C15—C16 | 1.386 (4) |
C1—H1A | 0.9900 | C15—H15 | 0.9500 |
C1—H1B | 0.9900 | C16—H16 | 0.9500 |
C2—C2i | 1.559 (6) | | |
| | | |
C11—O1—H1 | 111 (2) | N3—C3—H3B | 108.4 |
C2—N1—C3 | 114.9 (2) | N1—C3—H3B | 108.4 |
C2—N1—C1 | 114.8 (2) | H3A—C3—H3B | 107.5 |
C3—N1—C1 | 109.6 (2) | N3—C4—N2 | 111.6 (3) |
C4—N2—C1i | 107.8 (2) | N3—C4—H4A | 109.3 |
C4—N2—C1 | 107.8 (2) | N2—C4—H4A | 109.3 |
C1i—N2—C1 | 113.4 (3) | N3—C4—H4B | 109.3 |
C4—N3—C3i | 108.3 (2) | N2—C4—H4B | 109.3 |
C4—N3—C3 | 108.3 (2) | H4A—C4—H4B | 108.0 |
C3i—N3—C3 | 113.5 (3) | O1—C11—C12 | 117.0 (2) |
O3—N11—O2 | 122.8 (3) | O1—C11—C16 | 123.5 (2) |
O3—N11—C13 | 119.0 (2) | C12—C11—C16 | 119.5 (2) |
O2—N11—C13 | 118.2 (2) | C13—C12—C11 | 118.1 (2) |
N2—C1—N1 | 115.7 (2) | C13—C12—H12 | 120.9 |
N2—C1—H1A | 108.4 | C11—C12—H12 | 120.9 |
N1—C1—H1A | 108.4 | C12—C13—C14 | 123.7 (2) |
N2—C1—H1B | 108.4 | C12—C13—N11 | 117.3 (2) |
N1—C1—H1B | 108.4 | C14—C13—N11 | 119.0 (2) |
H1A—C1—H1B | 107.4 | C15—C14—C13 | 117.0 (2) |
N1—C2—C2i | 117.53 (13) | C15—C14—H14 | 121.5 |
N1—C2—H2A | 107.9 | C13—C14—H14 | 121.5 |
C2i—C2—H2A | 107.9 | C16—C15—C14 | 121.4 (2) |
N1—C2—H2B | 107.9 | C16—C15—H15 | 119.3 |
C2i—C2—H2B | 107.9 | C14—C15—H15 | 119.3 |
H2A—C2—H2B | 107.2 | C15—C16—C11 | 120.2 (2) |
N3—C3—N1 | 115.6 (2) | C15—C16—H16 | 119.9 |
N3—C3—H3A | 108.4 | C11—C16—H16 | 119.9 |
N1—C3—H3A | 108.4 | | |
| | | |
C4—N2—C1—N1 | −54.3 (3) | O1—C11—C12—C13 | −178.3 (2) |
C1i—N2—C1—N1 | 65.0 (4) | C16—C11—C12—C13 | 0.4 (3) |
C2—N1—C1—N2 | −84.3 (3) | C11—C12—C13—C14 | −0.2 (4) |
C3—N1—C1—N2 | 46.9 (3) | C11—C12—C13—N11 | 179.4 (2) |
C3—N1—C2—C2i | −64.1 (2) | O3—N11—C13—C12 | −2.9 (3) |
C1—N1—C2—C2i | 64.4 (2) | O2—N11—C13—C12 | 176.5 (3) |
C4—N3—C3—N1 | 54.7 (3) | O3—N11—C13—C14 | 176.8 (3) |
C3i—N3—C3—N1 | −65.6 (4) | O2—N11—C13—C14 | −3.9 (4) |
C2—N1—C3—N3 | 84.2 (3) | C12—C13—C14—C15 | −0.4 (4) |
C1—N1—C3—N3 | −46.8 (3) | N11—C13—C14—C15 | 180.0 (2) |
C3i—N3—C4—N2 | 61.73 (19) | C13—C14—C15—C16 | 0.9 (4) |
C3—N3—C4—N2 | −61.73 (19) | C14—C15—C16—C11 | −0.7 (4) |
C1i—N2—C4—N3 | −61.4 (2) | O1—C11—C16—C15 | 178.6 (3) |
C1—N2—C4—N3 | 61.4 (2) | C12—C11—C16—C15 | 0.1 (3) |
Symmetry code: (i) x, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.88 (4) | 1.84 (4) | 2.696 (3) | 162 (3) |
C4—H4A···O2ii | 0.99 | 2.56 | 3.476 (3) | 154 |
C4—H4B···O2iii | 0.99 | 2.56 | 3.476 (3) | 154 |
C15—H15···O1iv | 0.95 | 2.51 | 3.427 (3) | 161 |
Symmetry codes: (ii) x+1/2, y−1/2, z+1; (iii) x+1/2, −y+1/2, z+1; (iv) x, y, z−1. |
3-Nitrophenol–1,3,6,8-tetraazatricyclo[4.4.1.1
3,8]dodecane (2:1) (3a)
top
Crystal data top
C8H16N4·2C6H5NO3 | F(000) = 944 |
Mr = 446.47 | Dx = 1.421 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.159 (3) Å | Cell parameters from 11125 reflections |
b = 6.4931 (4) Å | θ = 3.5–25.8° |
c = 12.8070 (14) Å | µ = 0.11 mm−1 |
β = 106.338 (8)° | T = 173 K |
V = 2087.5 (4) Å3 | Plate, yellow |
Z = 4 | 0.26 × 0.24 × 0.09 mm |
Data collection top
Stoe IPDS II two-circle diffractometer | 3297 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.027 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −31→31 |
Tmin = 0.582, Tmax = 1.000 | k = −7→7 |
11125 measured reflections | l = −15→15 |
3505 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0416P)2 + 1.2092P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max < 0.001 |
wR(F2) = 0.087 | Δρmax = 0.14 e Å−3 |
S = 1.08 | Δρmin = −0.15 e Å−3 |
3505 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
298 parameters | Extinction coefficient: 0.0087 (10) |
2 restraints | Absolute structure: Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (9) |
Hydrogen site location: mixed | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.44528 (9) | 0.2931 (4) | 0.4785 (2) | 0.0231 (5) | |
N2 | 0.55900 (10) | 0.3302 (3) | 0.5346 (2) | 0.0244 (5) | |
N3 | 0.50770 (10) | 0.0032 (4) | 0.4661 (2) | 0.0252 (5) | |
N4 | 0.49760 (9) | 0.3696 (4) | 0.3449 (2) | 0.0247 (5) | |
C1 | 0.47168 (12) | 0.4020 (5) | 0.5808 (3) | 0.0337 (7) | |
H1A | 0.4651 | 0.3234 | 0.6419 | 0.040* | |
H1B | 0.4545 | 0.5383 | 0.5791 | 0.040* | |
C2 | 0.53212 (12) | 0.4353 (5) | 0.6047 (3) | 0.0370 (8) | |
H2A | 0.5386 | 0.5850 | 0.6008 | 0.044* | |
H2B | 0.5491 | 0.3915 | 0.6806 | 0.044* | |
C3 | 0.45716 (12) | 0.0699 (4) | 0.4817 (3) | 0.0272 (6) | |
H3A | 0.4553 | 0.0166 | 0.5530 | 0.033* | |
H3B | 0.4283 | 0.0022 | 0.4252 | 0.033* | |
C4 | 0.45002 (11) | 0.4014 (4) | 0.3795 (2) | 0.0264 (6) | |
H4A | 0.4190 | 0.3613 | 0.3185 | 0.032* | |
H4B | 0.4468 | 0.5510 | 0.3914 | 0.032* | |
C5 | 0.55491 (12) | 0.1024 (4) | 0.5363 (3) | 0.0305 (7) | |
H5A | 0.5863 | 0.0452 | 0.5177 | 0.037* | |
H5B | 0.5578 | 0.0605 | 0.6121 | 0.037* | |
C6 | 0.54774 (12) | 0.4195 (5) | 0.4247 (3) | 0.0300 (7) | |
H6A | 0.5496 | 0.5712 | 0.4327 | 0.036* | |
H6B | 0.5769 | 0.3776 | 0.3940 | 0.036* | |
C7 | 0.50771 (14) | −0.0199 (5) | 0.3531 (3) | 0.0351 (7) | |
H7A | 0.4801 | −0.1218 | 0.3180 | 0.042* | |
H7B | 0.5426 | −0.0771 | 0.3516 | 0.042* | |
C8 | 0.49764 (13) | 0.1784 (5) | 0.2851 (2) | 0.0306 (7) | |
H8A | 0.5252 | 0.1892 | 0.2461 | 0.037* | |
H8B | 0.4628 | 0.1655 | 0.2296 | 0.037* | |
N11 | 0.15684 (11) | 0.4297 (6) | 0.3322 (2) | 0.0422 (8) | |
O11 | 0.33946 (9) | 0.2081 (4) | 0.4343 (2) | 0.0402 (6) | |
H11 | 0.3734 (18) | 0.252 (7) | 0.449 (3) | 0.048 (11)* | |
O12 | 0.14277 (10) | 0.2493 (5) | 0.3334 (2) | 0.0594 (8) | |
O13 | 0.12521 (9) | 0.5734 (5) | 0.2996 (2) | 0.0596 (8) | |
C11 | 0.30418 (11) | 0.3667 (5) | 0.4201 (2) | 0.0267 (6) | |
C12 | 0.25005 (12) | 0.3201 (5) | 0.3832 (2) | 0.0308 (7) | |
H12 | 0.2383 | 0.1823 | 0.3668 | 0.037* | |
C13 | 0.21382 (11) | 0.4798 (6) | 0.3711 (2) | 0.0310 (7) | |
C14 | 0.22866 (13) | 0.6835 (6) | 0.3947 (3) | 0.0355 (8) | |
H14 | 0.2028 | 0.7896 | 0.3859 | 0.043* | |
C15 | 0.28227 (14) | 0.7260 (5) | 0.4311 (3) | 0.0358 (7) | |
H15 | 0.2936 | 0.8642 | 0.4477 | 0.043* | |
C16 | 0.32020 (12) | 0.5711 (5) | 0.4442 (3) | 0.0316 (7) | |
H16 | 0.3570 | 0.6039 | 0.4696 | 0.038* | |
N21 | 0.84474 (10) | 0.5845 (5) | 0.6896 (2) | 0.0377 (7) | |
O21 | 0.66682 (9) | 0.3172 (3) | 0.6068 (2) | 0.0402 (7) | |
H21 | 0.635 (2) | 0.344 (7) | 0.582 (4) | 0.061 (14)* | |
O22 | 0.86017 (10) | 0.4093 (4) | 0.6811 (3) | 0.0532 (8) | |
O23 | 0.87489 (10) | 0.7320 (5) | 0.7172 (3) | 0.0589 (8) | |
C21 | 0.69850 (11) | 0.4855 (4) | 0.6209 (2) | 0.0258 (6) | |
C22 | 0.75329 (11) | 0.4526 (5) | 0.6475 (3) | 0.0281 (7) | |
H22 | 0.7674 | 0.3168 | 0.6548 | 0.034* | |
C23 | 0.78669 (12) | 0.6217 (5) | 0.6629 (2) | 0.0274 (6) | |
C24 | 0.76851 (13) | 0.8228 (5) | 0.6538 (3) | 0.0322 (7) | |
H24 | 0.7925 | 0.9360 | 0.6656 | 0.039* | |
C25 | 0.71378 (13) | 0.8522 (5) | 0.6266 (3) | 0.0319 (7) | |
H25 | 0.6999 | 0.9883 | 0.6186 | 0.038* | |
C26 | 0.67895 (12) | 0.6860 (5) | 0.6109 (2) | 0.0274 (7) | |
H26 | 0.6416 | 0.7093 | 0.5932 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0177 (11) | 0.0254 (12) | 0.0264 (12) | 0.0001 (9) | 0.0063 (10) | 0.0009 (10) |
N2 | 0.0196 (11) | 0.0234 (12) | 0.0282 (13) | 0.0034 (10) | 0.0035 (9) | −0.0021 (10) |
N3 | 0.0234 (11) | 0.0203 (11) | 0.0318 (13) | 0.0001 (9) | 0.0074 (10) | 0.0028 (10) |
N4 | 0.0224 (11) | 0.0237 (12) | 0.0267 (12) | 0.0002 (9) | 0.0051 (9) | 0.0059 (10) |
C1 | 0.0282 (15) | 0.0410 (18) | 0.0323 (17) | 0.0010 (14) | 0.0091 (13) | −0.0085 (14) |
C2 | 0.0280 (15) | 0.049 (2) | 0.0329 (17) | −0.0013 (14) | 0.0065 (13) | −0.0157 (15) |
C3 | 0.0233 (14) | 0.0270 (14) | 0.0329 (15) | 0.0012 (12) | 0.0106 (12) | 0.0100 (13) |
C4 | 0.0228 (13) | 0.0239 (14) | 0.0301 (15) | 0.0042 (11) | 0.0034 (12) | 0.0055 (12) |
C5 | 0.0225 (13) | 0.0243 (15) | 0.0391 (17) | 0.0031 (12) | −0.0005 (12) | 0.0061 (13) |
C6 | 0.0231 (14) | 0.0289 (15) | 0.0358 (17) | −0.0049 (11) | 0.0048 (12) | 0.0068 (13) |
C7 | 0.0417 (18) | 0.0287 (16) | 0.0390 (18) | −0.0035 (13) | 0.0178 (15) | −0.0049 (13) |
C8 | 0.0297 (15) | 0.0364 (18) | 0.0252 (15) | 0.0032 (12) | 0.0069 (12) | 0.0012 (12) |
N11 | 0.0211 (13) | 0.076 (2) | 0.0289 (14) | −0.0010 (14) | 0.0055 (11) | −0.0050 (14) |
O11 | 0.0204 (11) | 0.0334 (12) | 0.0642 (17) | −0.0017 (10) | 0.0076 (11) | −0.0007 (11) |
O12 | 0.0291 (13) | 0.084 (2) | 0.0609 (18) | −0.0197 (14) | 0.0050 (12) | −0.0018 (15) |
O13 | 0.0238 (13) | 0.095 (2) | 0.0580 (18) | 0.0156 (14) | 0.0078 (12) | −0.0007 (16) |
C11 | 0.0220 (14) | 0.0308 (15) | 0.0266 (15) | 0.0019 (11) | 0.0054 (12) | 0.0014 (12) |
C12 | 0.0258 (15) | 0.0383 (18) | 0.0288 (16) | −0.0042 (13) | 0.0084 (12) | −0.0022 (13) |
C13 | 0.0203 (14) | 0.052 (2) | 0.0208 (15) | 0.0022 (14) | 0.0062 (12) | −0.0016 (13) |
C14 | 0.0275 (15) | 0.049 (2) | 0.0308 (17) | 0.0090 (14) | 0.0097 (13) | −0.0038 (15) |
C15 | 0.0384 (17) | 0.0337 (18) | 0.0357 (18) | 0.0006 (14) | 0.0113 (14) | −0.0048 (14) |
C16 | 0.0227 (14) | 0.0407 (19) | 0.0301 (16) | −0.0035 (13) | 0.0052 (12) | −0.0029 (14) |
N21 | 0.0237 (13) | 0.0477 (18) | 0.0387 (15) | −0.0027 (13) | 0.0039 (11) | 0.0018 (14) |
O21 | 0.0184 (11) | 0.0252 (12) | 0.0715 (18) | 0.0016 (9) | 0.0036 (12) | −0.0019 (11) |
O22 | 0.0256 (12) | 0.0537 (17) | 0.073 (2) | 0.0081 (12) | 0.0027 (12) | 0.0022 (14) |
O23 | 0.0296 (13) | 0.0651 (18) | 0.077 (2) | −0.0200 (13) | 0.0070 (13) | −0.0159 (16) |
C21 | 0.0238 (14) | 0.0236 (15) | 0.0273 (16) | 0.0030 (12) | 0.0030 (11) | −0.0006 (12) |
C22 | 0.0249 (15) | 0.0262 (16) | 0.0310 (15) | 0.0056 (12) | 0.0043 (12) | 0.0002 (12) |
C23 | 0.0221 (14) | 0.0343 (16) | 0.0227 (14) | −0.0029 (12) | 0.0014 (11) | −0.0012 (12) |
C24 | 0.0380 (18) | 0.0298 (17) | 0.0303 (15) | −0.0084 (13) | 0.0120 (14) | −0.0043 (13) |
C25 | 0.0427 (18) | 0.0228 (14) | 0.0301 (16) | 0.0049 (13) | 0.0101 (14) | −0.0001 (12) |
C26 | 0.0259 (15) | 0.0279 (16) | 0.0282 (15) | 0.0077 (12) | 0.0074 (12) | 0.0029 (12) |
Geometric parameters (Å, º) top
N1—C1 | 1.478 (4) | N11—O12 | 1.229 (5) |
N1—C3 | 1.481 (4) | N11—O13 | 1.239 (4) |
N1—C4 | 1.484 (4) | N11—C13 | 1.469 (4) |
N2—C2 | 1.457 (4) | O11—C11 | 1.360 (4) |
N2—C6 | 1.473 (4) | O11—H11 | 0.90 (5) |
N2—C5 | 1.484 (4) | C11—C12 | 1.394 (4) |
N3—C7 | 1.455 (4) | C11—C16 | 1.400 (4) |
N3—C3 | 1.457 (4) | C12—C13 | 1.384 (5) |
N3—C5 | 1.457 (4) | C12—H12 | 0.9500 |
N4—C4 | 1.449 (4) | C13—C14 | 1.388 (5) |
N4—C6 | 1.455 (4) | C14—C15 | 1.376 (5) |
N4—C8 | 1.459 (4) | C14—H14 | 0.9500 |
C1—C2 | 1.539 (4) | C15—C16 | 1.389 (5) |
C1—H1A | 0.9900 | C15—H15 | 0.9500 |
C1—H1B | 0.9900 | C16—H16 | 0.9500 |
C2—H2A | 0.9900 | N21—O22 | 1.222 (4) |
C2—H2B | 0.9900 | N21—O23 | 1.228 (4) |
C3—H3A | 0.9900 | N21—C23 | 1.480 (4) |
C3—H3B | 0.9900 | O21—C21 | 1.353 (4) |
C4—H4A | 0.9900 | O21—H21 | 0.83 (5) |
C4—H4B | 0.9900 | C21—C26 | 1.391 (4) |
C5—H5A | 0.9900 | C21—C22 | 1.393 (4) |
C5—H5B | 0.9900 | C22—C23 | 1.383 (4) |
C6—H6A | 0.9900 | C22—H22 | 0.9500 |
C6—H6B | 0.9900 | C23—C24 | 1.383 (4) |
C7—C8 | 1.535 (5) | C24—C25 | 1.388 (5) |
C7—H7A | 0.9900 | C24—H24 | 0.9500 |
C7—H7B | 0.9900 | C25—C26 | 1.390 (4) |
C8—H8A | 0.9900 | C25—H25 | 0.9500 |
C8—H8B | 0.9900 | C26—H26 | 0.9500 |
| | | |
C1—N1—C3 | 113.7 (2) | C8—C7—H7B | 108.4 |
C1—N1—C4 | 113.6 (2) | H7A—C7—H7B | 107.5 |
C3—N1—C4 | 114.8 (2) | N4—C8—C7 | 116.2 (3) |
C2—N2—C6 | 113.8 (2) | N4—C8—H8A | 108.2 |
C2—N2—C5 | 114.1 (3) | C7—C8—H8A | 108.2 |
C6—N2—C5 | 114.2 (2) | N4—C8—H8B | 108.2 |
C7—N3—C3 | 114.9 (2) | C7—C8—H8B | 108.2 |
C7—N3—C5 | 115.0 (2) | H8A—C8—H8B | 107.4 |
C3—N3—C5 | 115.3 (3) | O12—N11—O13 | 123.2 (3) |
C4—N4—C6 | 115.8 (2) | O12—N11—C13 | 119.1 (3) |
C4—N4—C8 | 114.2 (2) | O13—N11—C13 | 117.7 (3) |
C6—N4—C8 | 115.1 (2) | C11—O11—H11 | 112 (3) |
N1—C1—C2 | 116.2 (3) | O11—C11—C12 | 117.9 (3) |
N1—C1—H1A | 108.2 | O11—C11—C16 | 122.6 (3) |
C2—C1—H1A | 108.2 | C12—C11—C16 | 119.5 (3) |
N1—C1—H1B | 108.2 | C13—C12—C11 | 118.3 (3) |
C2—C1—H1B | 108.2 | C13—C12—H12 | 120.9 |
H1A—C1—H1B | 107.4 | C11—C12—H12 | 120.9 |
N2—C2—C1 | 117.3 (3) | C12—C13—C14 | 123.3 (3) |
N2—C2—H2A | 108.0 | C12—C13—N11 | 118.0 (3) |
C1—C2—H2A | 108.0 | C14—C13—N11 | 118.7 (3) |
N2—C2—H2B | 108.0 | C15—C14—C13 | 117.5 (3) |
C1—C2—H2B | 108.0 | C15—C14—H14 | 121.3 |
H2A—C2—H2B | 107.2 | C13—C14—H14 | 121.3 |
N3—C3—N1 | 118.6 (2) | C14—C15—C16 | 121.4 (3) |
N3—C3—H3A | 107.7 | C14—C15—H15 | 119.3 |
N1—C3—H3A | 107.7 | C16—C15—H15 | 119.3 |
N3—C3—H3B | 107.7 | C15—C16—C11 | 120.0 (3) |
N1—C3—H3B | 107.7 | C15—C16—H16 | 120.0 |
H3A—C3—H3B | 107.1 | C11—C16—H16 | 120.0 |
N4—C4—N1 | 118.6 (2) | O22—N21—O23 | 123.4 (3) |
N4—C4—H4A | 107.7 | O22—N21—C23 | 118.4 (3) |
N1—C4—H4A | 107.7 | O23—N21—C23 | 118.2 (3) |
N4—C4—H4B | 107.7 | C21—O21—H21 | 113 (3) |
N1—C4—H4B | 107.7 | O21—C21—C26 | 123.2 (3) |
H4A—C4—H4B | 107.1 | O21—C21—C22 | 117.3 (3) |
N3—C5—N2 | 118.9 (2) | C26—C21—C22 | 119.5 (3) |
N3—C5—H5A | 107.6 | C23—C22—C21 | 118.6 (3) |
N2—C5—H5A | 107.6 | C23—C22—H22 | 120.7 |
N3—C5—H5B | 107.6 | C21—C22—H22 | 120.7 |
N2—C5—H5B | 107.6 | C22—C23—C24 | 123.3 (3) |
H5A—C5—H5B | 107.0 | C22—C23—N21 | 118.0 (3) |
N4—C6—N2 | 118.8 (2) | C24—C23—N21 | 118.7 (3) |
N4—C6—H6A | 107.6 | C23—C24—C25 | 117.2 (3) |
N2—C6—H6A | 107.6 | C23—C24—H24 | 121.4 |
N4—C6—H6B | 107.6 | C25—C24—H24 | 121.4 |
N2—C6—H6B | 107.6 | C24—C25—C26 | 121.1 (3) |
H6A—C6—H6B | 107.0 | C24—C25—H25 | 119.4 |
N3—C7—C8 | 115.4 (3) | C26—C25—H25 | 119.4 |
N3—C7—H7A | 108.4 | C25—C26—C21 | 120.3 (3) |
C8—C7—H7A | 108.4 | C25—C26—H26 | 119.9 |
N3—C7—H7B | 108.4 | C21—C26—H26 | 119.9 |
| | | |
C3—N1—C1—C2 | 72.9 (4) | C16—C11—C12—C13 | 0.4 (5) |
C4—N1—C1—C2 | −60.8 (4) | C11—C12—C13—C14 | −0.5 (5) |
C6—N2—C2—C1 | 73.0 (4) | C11—C12—C13—N11 | 180.0 (3) |
C5—N2—C2—C1 | −60.6 (4) | O12—N11—C13—C12 | 15.0 (4) |
N1—C1—C2—N2 | −9.3 (5) | O13—N11—C13—C12 | −165.0 (3) |
C7—N3—C3—N1 | −85.0 (3) | O12—N11—C13—C14 | −164.5 (3) |
C5—N3—C3—N1 | 52.3 (4) | O13—N11—C13—C14 | 15.5 (4) |
C1—N1—C3—N3 | −79.7 (3) | C12—C13—C14—C15 | 0.4 (5) |
C4—N1—C3—N3 | 53.5 (3) | N11—C13—C14—C15 | 179.9 (3) |
C6—N4—C4—N1 | −57.2 (3) | C13—C14—C15—C16 | −0.2 (5) |
C8—N4—C4—N1 | 80.0 (3) | C14—C15—C16—C11 | 0.1 (5) |
C1—N1—C4—N4 | 84.3 (3) | O11—C11—C16—C15 | −178.1 (3) |
C3—N1—C4—N4 | −48.9 (3) | C12—C11—C16—C15 | −0.2 (5) |
C7—N3—C5—N2 | 80.1 (4) | O21—C21—C22—C23 | −179.7 (3) |
C3—N3—C5—N2 | −57.2 (4) | C26—C21—C22—C23 | −0.1 (4) |
C2—N2—C5—N3 | 84.1 (4) | C21—C22—C23—C24 | 0.2 (5) |
C6—N2—C5—N3 | −49.2 (4) | C21—C22—C23—N21 | −179.2 (3) |
C4—N4—C6—N2 | 51.8 (3) | O22—N21—C23—C22 | 10.5 (5) |
C8—N4—C6—N2 | −85.1 (3) | O23—N21—C23—C22 | −170.7 (3) |
C2—N2—C6—N4 | −79.0 (3) | O22—N21—C23—C24 | −168.9 (3) |
C5—N2—C6—N4 | 54.5 (4) | O23—N21—C23—C24 | 9.9 (5) |
C3—N3—C7—C8 | 63.2 (3) | C22—C23—C24—C25 | −0.6 (5) |
C5—N3—C7—C8 | −74.3 (3) | N21—C23—C24—C25 | 178.8 (3) |
C4—N4—C8—C7 | −75.2 (3) | C23—C24—C25—C26 | 0.9 (5) |
C6—N4—C8—C7 | 62.4 (4) | C24—C25—C26—C21 | −0.8 (5) |
N3—C7—C8—N4 | 9.3 (4) | O21—C21—C26—C25 | 179.9 (3) |
O11—C11—C12—C13 | 178.4 (3) | C22—C21—C26—C25 | 0.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N1 | 0.90 (5) | 1.83 (5) | 2.722 (3) | 170 (4) |
O21—H21···N2 | 0.83 (5) | 1.90 (5) | 2.711 (3) | 164 (5) |
C15—H15···O11i | 0.95 | 2.56 | 3.465 (4) | 158 |
C25—H25···O21i | 0.95 | 2.29 | 3.243 (4) | 178 |
Symmetry code: (i) x, y+1, z. |
Selected bond lengths (Å) for the aminal cages structures
(1)–(3) of (1a), (2a) and (3a) topHMTA is 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
and TATD is 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane. |
Parameter | (1a) | (2a) | (3a) | HMTAa | TATDb |
α1 | 1.471 (4) | 1.493 (4) | 1.481 (4) | 1.462 (5) | 1.456 (2) |
α2 | 1.481 (3) | 1.477 (3) | 1.484 (4) | 1.462 (5) | 1.456 (2) |
α3 | 1.479 (4) | 1.463 (4) | 1.478 (4) | 1.462 (5) | 1.459 (5) |
β1 | 1.470 (3) | 1.466 (3) | 1.484 (4) | 1.462 (5) | 1.456 (2) |
β2 | 1.478 (3) | 1.466 (3) | 1.473 (4) | 1.462 (5) | 1.456 (2) |
β3 | 1.478 (3) | 1.465 (5) | 1.457 (4) | 1.462 (5) | 1.459 (5) |
γ1 | 1.461 (3) | 1.465 (3) | 1.457 (4) | 1.462 (5) | 1.456 (2) |
γ2 | 1.464 (4) | 1.465 (3) | 1.457 (4) | 1.462 (5) | 1.456 (2) |
γ3 | 1.459 (3) | 1.462 (6) | 1.455 (4) | 1.462 (5) | 1.459 (5) |
δ1 | 1.470 (4) | | 1.449 (4) | 1.462 (5) | 1.456 (2) |
δ2 | 1.474 (3) | | 1.455 (4) | 1.462 (5) | 1.456 (2) |
δ3 | 1.481 (3) | | 1.459 (4) | 1.462 (5) | 1.459 (5) |
References: (a) Terpstra et al. (1993); (b) Rivera
et al. (2014). |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.