organic compounds
3,3′-(Dodecane-1,12-diyl)bis(1-methylimidazolium) 5,5′-azotetrazolate heptahydrate
aUniversity of Innsbruck, Faculty of Chemistry and Pharmacy, Innrain 80–82, 6020 Innsbruck, Austria
*Correspondence e-mail: gerhard.laus@uibk.ac.at
The title compound, C20H36N4·C2N10·7H2O, was obtained by reaction of 1-methylimidazole with 1,12-dibromododecane, followed by repeated ion metathesis (bromide → sulfate → azotetrazolate). An intricate network of hydrogen bonds is formed between anions and water molecules, leading to a layered arrangement parallel to (101).
Keywords: crystal structure; azotetrazolate; dianion; dication; imidazole.
CCDC reference: 1571912
Structure description
Two heterocyclic cations joined by hydrocarbon linkage chains and paired with different anions constitute a new class of ionic liquids. Dicationic imidazolium-based ionic liquids exhibit superior thermal stabilities compared to those of traditional ionic liquids (Anderson et al., 2005). Coincidentally, heterocyclic dianions are of interest as components for nitrogen-rich salts (Laus et al., 2016) or potential explosives (Singh et al., 2006). A combination of these dications and dianions was presumed to furnish products with interesting structural attributes. Repeated ion metathesis (bromide → sulfate → azotetrazolate) was successfully employed for the synthesis of the desired salts, the of one of which is reported here.
In the ) which can be adequately described by graph-set symbols (Etter, 1990; Etter et al., 1990). One azotetrazolate dianion is surrounded by various water molecules enclosing pairs of R44(10), R33(11) and R77(16) ring motifs each, as well as one R44(9) and one R77(15) ring motif (Fig. 1). The planar dianion [the maximum deviation from the least-squares plane is 0.027 (2) Å for N9] and seven water molecules are located near the (101) plane, whereas the bar-shaped dications are found above and beneath this layer (Fig. 2). The dihedral angle between the two 1-methylimidazolium moieties in the dication is 8.57 (15)°.
of the title hydrated salt, an intricate network of O—H⋯O and O—H⋯N hydrogen-bonded anions and water molecules is observed (Table 1Related structures of geminal dications with traditional anions (Anderson et al., 2005) as well as related azotetrazolate salts with traditional cations (Laus et al., 2012) have been reported.
Synthesis and crystallization
Silver sulfate (156 mg, 0.50 mmol) was added to a solution of 3,3′-(dodecane-1,12-diyl)bis(1-methylimidazolium) bromide (246 mg, 0.50 mmol; Tadesse et al., 2012) in water (5 ml). The mixture was stirred at 323 K for 10 min and ultrasonicated for 5 min. Subsequently, the precipitate was removed by centrifugation. Barium 5,5′-azotetrazolate pentahydrate (196 mg, 0.50 mmol; Hammerl et al., 2002) was added to the supernatant, and the mixture was again stirred at 323 K for 10 min and ultrasonicated for 5 min. After centrifugation, the supernatant solution was filtered (0.45 µm) and taken to dryness in a rotary evaporator under reduced pressure, the temperature not exceeding 323 K. The yellow residue was recrystallized from hot water, collected by filtration and vacuum-dried to yield 280 mg (90%) of the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 9.29 (s, 2H), 7.81 (s, 2H), 7.73 (s, 2H), 4.18 (t, J = 7.2 Hz, 4H), 3.88 (s, 6H), 1.74 (m, 4H), 1.17 (m, 16H). 13C NMR (DMSO-d6, 75 MHz): δ 173.5, 136.7, 123.6, 122.3, 48.8, 35.8, 29.4, 28.8, 28.7, 28.3, 25.4. IR (neat): ν 3351 s, 2919 m, 2855 m, 1651 w, 1588 m, 1473 m, 1394 m, 1163 s, 732 m cm−1.
Refinement
Crystal data, data collection and structure . Hydrogen atoms bound to water molecules were found from difference maps and were included in the with distance restraints of d(O—H) = 0.82 Å. Three reflections, (101), (202) and (505), were omitted because of poor agreement between calculated and observed intensities.
details are summarized in Table 2
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Structural data
CCDC reference: 1571912
https://doi.org/10.1107/S241431461701255X/wm4055sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461701255X/wm4055Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461701255X/wm4055Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S241431461701255X/wm4055Isup4.cml
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008).C20H36N4·C2N10·7H2O | F(000) = 672 |
Mr = 622.76 | Dx = 1.243 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2847 (3) Å | Cell parameters from 9972 reflections |
b = 8.9932 (4) Å | θ = 2.4–25.6° |
c = 25.3962 (11) Å | µ = 0.10 mm−1 |
β = 91.062 (1)° | T = 183 K |
V = 1663.49 (12) Å3 | Prism, colourless |
Z = 2 | 0.17 × 0.12 × 0.08 mm |
Bruker D8 QUEST PHOTON 100 diffractometer | 6171 independent reflections |
Radiation source: Incoatec Microfocus | 5428 reflections with I > 2σ(I) |
Multi layered optics monochromator | Rint = 0.032 |
Detector resolution: 10.4 pixels mm-1 | θmax = 25.5°, θmin = 2.4° |
φ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −10→10 |
Tmin = 0.848, Tmax = 0.888 | l = −30→28 |
29637 measured reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1318P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max < 0.001 |
wR(F2) = 0.081 | Δρmax = 0.17 e Å−3 |
S = 1.04 | Δρmin = −0.15 e Å−3 |
6171 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
447 parameters | Extinction coefficient: 0.026 (2) |
15 restraints | Absolute structure: Flack x determined using 2270 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
Hydrogen site location: mixed | Absolute structure parameter: −0.2 (4) |
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. |
Refinement. Hydrogens at water molecules O1–O7 were found and refined with bond restraints (d=83 (2)pm). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8692 (3) | 0.4847 (2) | 0.12571 (8) | 0.0307 (5) | |
N2 | 0.8791 (3) | 0.6275 (2) | 0.11135 (8) | 0.0373 (5) | |
N3 | 0.8434 (3) | 0.7122 (2) | 0.15240 (8) | 0.0400 (5) | |
N4 | 0.8089 (3) | 0.6279 (2) | 0.19435 (8) | 0.0340 (5) | |
N5 | 0.8068 (3) | 0.3557 (2) | 0.20434 (8) | 0.0261 (4) | |
N6 | 0.7696 (3) | 0.3769 (2) | 0.25202 (7) | 0.0263 (4) | |
N7 | 0.7674 (3) | 0.1051 (2) | 0.26322 (8) | 0.0329 (5) | |
N8 | 0.7297 (3) | 0.0225 (2) | 0.30551 (8) | 0.0378 (5) | |
N9 | 0.6900 (3) | 0.1093 (2) | 0.34584 (8) | 0.0336 (5) | |
N10 | 0.7021 (3) | 0.2510 (2) | 0.33069 (7) | 0.0292 (5) | |
N11 | 0.5418 (3) | 1.5010 (2) | −0.02519 (7) | 0.0305 (5) | |
N12 | 0.5847 (3) | 1.4521 (2) | −0.10701 (8) | 0.0348 (5) | |
N13 | −0.1024 (3) | 1.2390 (2) | 0.58176 (7) | 0.0290 (5) | |
N14 | −0.1585 (3) | 1.3001 (2) | 0.66194 (7) | 0.0307 (5) | |
C1 | 0.8260 (3) | 0.4893 (3) | 0.17634 (8) | 0.0251 (5) | |
C2 | 0.7486 (3) | 0.2445 (3) | 0.28024 (8) | 0.0241 (5) | |
C3 | 0.4658 (3) | 1.5052 (3) | −0.07287 (9) | 0.0349 (6) | |
H3 | 0.3458 | 1.5405 | −0.0813 | 0.042* | |
C4 | 0.7151 (3) | 1.4425 (3) | −0.02907 (10) | 0.0353 (6) | |
H4 | 0.8004 | 1.4263 | −0.0009 | 0.042* | |
C5 | 0.7411 (3) | 1.4128 (3) | −0.07982 (10) | 0.0380 (6) | |
H5 | 0.8490 | 1.3717 | −0.0945 | 0.046* | |
C6 | 0.5567 (4) | 1.4409 (4) | −0.16425 (10) | 0.0505 (8) | |
H6A | 0.4453 | 1.4954 | −0.1747 | 0.076* | |
H6B | 0.5433 | 1.3362 | −0.1742 | 0.076* | |
H6C | 0.6626 | 1.4837 | −0.1820 | 0.076* | |
C7 | 0.4564 (4) | 1.5521 (3) | 0.02358 (10) | 0.0381 (6) | |
H7A | 0.3320 | 1.5906 | 0.0152 | 0.046* | |
H7B | 0.5299 | 1.6347 | 0.0387 | 0.046* | |
C8 | 0.4423 (3) | 1.4289 (3) | 0.06399 (9) | 0.0320 (6) | |
H8A | 0.5644 | 1.3825 | 0.0694 | 0.038* | |
H8B | 0.3569 | 1.3515 | 0.0506 | 0.038* | |
C9 | 0.3744 (3) | 1.4871 (3) | 0.11621 (9) | 0.0338 (6) | |
H9A | 0.4631 | 1.5613 | 0.1301 | 0.041* | |
H9B | 0.2556 | 1.5384 | 0.1102 | 0.041* | |
C10 | 0.3493 (4) | 1.3665 (3) | 0.15710 (9) | 0.0319 (6) | |
H10A | 0.4637 | 1.3074 | 0.1600 | 0.038* | |
H10B | 0.2498 | 1.2990 | 0.1450 | 0.038* | |
C11 | 0.3028 (3) | 1.4261 (3) | 0.21137 (9) | 0.0311 (6) | |
H11A | 0.1935 | 1.4910 | 0.2079 | 0.037* | |
H11B | 0.4063 | 1.4883 | 0.2243 | 0.037* | |
C12 | 0.2647 (3) | 1.3067 (3) | 0.25226 (9) | 0.0309 (5) | |
H12A | 0.1618 | 1.2437 | 0.2394 | 0.037* | |
H12B | 0.3744 | 1.2424 | 0.2563 | 0.037* | |
C13 | 0.2169 (3) | 1.3705 (3) | 0.30569 (9) | 0.0313 (6) | |
H13A | 0.3160 | 1.4393 | 0.3171 | 0.038* | |
H13B | 0.1026 | 1.4294 | 0.3018 | 0.038* | |
C14 | 0.1903 (3) | 1.2553 (3) | 0.34859 (9) | 0.0300 (5) | |
H14A | 0.3072 | 1.2013 | 0.3546 | 0.036* | |
H14B | 0.0971 | 1.1822 | 0.3365 | 0.036* | |
C15 | 0.1296 (3) | 1.3233 (3) | 0.40039 (9) | 0.0303 (6) | |
H15A | 0.2243 | 1.3950 | 0.4126 | 0.036* | |
H15B | 0.0145 | 1.3795 | 0.3939 | 0.036* | |
C16 | 0.0977 (4) | 1.2114 (3) | 0.44382 (9) | 0.0314 (6) | |
H16A | 0.2131 | 1.1564 | 0.4511 | 0.038* | |
H16B | 0.0039 | 1.1387 | 0.4318 | 0.038* | |
C17 | 0.0341 (3) | 1.2848 (3) | 0.49451 (9) | 0.0311 (6) | |
H17A | 0.1332 | 1.3493 | 0.5087 | 0.037* | |
H17B | −0.0740 | 1.3483 | 0.4866 | 0.037* | |
C18 | −0.0161 (4) | 1.1707 (3) | 0.53555 (9) | 0.0332 (6) | |
H18A | −0.1018 | 1.0974 | 0.5196 | 0.040* | |
H18B | 0.0961 | 1.1169 | 0.5472 | 0.040* | |
C19 | −0.0403 (3) | 1.2306 (3) | 0.63118 (9) | 0.0319 (6) | |
H19 | 0.0699 | 1.1829 | 0.6426 | 0.038* | |
C20 | −0.2646 (3) | 1.3162 (3) | 0.58112 (9) | 0.0349 (6) | |
H20 | −0.3385 | 1.3386 | 0.5509 | 0.042* | |
C21 | −0.2997 (3) | 1.3544 (3) | 0.63103 (9) | 0.0336 (6) | |
H21 | −0.4030 | 1.4088 | 0.6428 | 0.040* | |
C22 | −0.1416 (4) | 1.3157 (4) | 0.71928 (9) | 0.0455 (7) | |
H22A | −0.0381 | 1.2557 | 0.7323 | 0.068* | |
H22B | −0.2549 | 1.2815 | 0.7356 | 0.068* | |
H22C | −0.1204 | 1.4204 | 0.7283 | 0.068* | |
O1 | 1.1165 (3) | 0.2885 (3) | −0.01317 (9) | 0.0604 (6) | |
H11O | 1.119 (5) | 0.234 (4) | −0.0413 (12) | 0.081 (13)* | |
H12O | 1.057 (6) | 0.238 (6) | 0.0114 (16) | 0.13 (2)* | |
O2 | 0.9157 (3) | 0.1993 (3) | 0.07677 (9) | 0.0511 (6) | |
H21O | 0.900 (4) | 0.283 (3) | 0.0887 (12) | 0.053 (10)* | |
H22O | 0.950 (6) | 0.140 (5) | 0.1007 (15) | 0.114 (19)* | |
O3 | 0.9542 (3) | 0.0143 (2) | 0.16588 (9) | 0.0564 (6) | |
H31O | 0.904 (5) | 0.056 (5) | 0.1916 (12) | 0.090 (14)* | |
H32O | 0.911 (6) | −0.073 (4) | 0.1609 (18) | 0.112 (17)* | |
O4 | 0.6059 (3) | −0.2736 (2) | 0.28580 (8) | 0.0447 (5) | |
H41O | 0.656 (4) | −0.187 (3) | 0.2911 (13) | 0.060 (10)* | |
H42O | 0.664 (4) | −0.308 (4) | 0.2595 (10) | 0.060 (10)* | |
O5 | 0.6601 (3) | −0.4551 (2) | 0.37380 (8) | 0.0422 (5) | |
H51O | 0.624 (6) | −0.400 (4) | 0.3475 (13) | 0.095 (15)* | |
H52O | 0.672 (4) | −0.539 (3) | 0.3618 (13) | 0.054 (10)* | |
O6 | 0.5478 (3) | −0.5538 (3) | 0.47071 (8) | 0.0532 (6) | |
H61O | 0.564 (5) | −0.507 (4) | 0.4400 (11) | 0.075 (11)* | |
H62O | 0.492 (5) | −0.493 (4) | 0.4895 (13) | 0.069 (11)* | |
O7 | 0.4008 (3) | −0.3607 (3) | 0.54270 (8) | 0.0468 (5) | |
H71O | 0.431 (6) | −0.270 (3) | 0.5374 (16) | 0.091 (15)* | |
H72O | 0.383 (5) | −0.379 (4) | 0.5748 (10) | 0.071 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0356 (11) | 0.0304 (11) | 0.0264 (10) | 0.0008 (9) | 0.0036 (8) | 0.0002 (9) |
N2 | 0.0483 (14) | 0.0328 (13) | 0.0310 (12) | 0.0018 (10) | 0.0074 (10) | 0.0034 (10) |
N3 | 0.0570 (14) | 0.0296 (12) | 0.0337 (12) | −0.0005 (10) | 0.0102 (10) | 0.0017 (10) |
N4 | 0.0458 (13) | 0.0280 (12) | 0.0285 (11) | 0.0005 (10) | 0.0061 (9) | 0.0009 (9) |
N5 | 0.0272 (11) | 0.0263 (11) | 0.0249 (11) | 0.0000 (8) | 0.0023 (8) | −0.0034 (8) |
N6 | 0.0249 (10) | 0.0282 (10) | 0.0258 (11) | 0.0016 (8) | 0.0012 (8) | −0.0014 (9) |
N7 | 0.0431 (13) | 0.0273 (11) | 0.0284 (11) | −0.0015 (9) | 0.0082 (9) | −0.0021 (9) |
N8 | 0.0508 (13) | 0.0284 (12) | 0.0346 (12) | −0.0033 (10) | 0.0087 (10) | −0.0013 (10) |
N9 | 0.0404 (13) | 0.0298 (12) | 0.0308 (11) | −0.0021 (10) | 0.0087 (9) | −0.0015 (9) |
N10 | 0.0330 (11) | 0.0275 (11) | 0.0274 (10) | −0.0006 (9) | 0.0048 (8) | −0.0024 (9) |
N11 | 0.0325 (11) | 0.0330 (12) | 0.0261 (10) | 0.0009 (9) | 0.0051 (8) | 0.0020 (9) |
N12 | 0.0386 (12) | 0.0405 (13) | 0.0257 (10) | −0.0052 (10) | 0.0059 (9) | 0.0022 (10) |
N13 | 0.0368 (11) | 0.0258 (10) | 0.0245 (10) | 0.0034 (9) | 0.0052 (8) | 0.0009 (9) |
N14 | 0.0346 (11) | 0.0345 (11) | 0.0231 (10) | −0.0019 (10) | 0.0049 (8) | −0.0005 (9) |
C1 | 0.0243 (12) | 0.0254 (12) | 0.0257 (12) | 0.0012 (10) | 0.0016 (9) | −0.0028 (10) |
C2 | 0.0241 (12) | 0.0244 (12) | 0.0240 (11) | 0.0008 (10) | 0.0022 (9) | −0.0028 (10) |
C3 | 0.0347 (14) | 0.0412 (15) | 0.0290 (13) | 0.0039 (12) | 0.0013 (11) | 0.0046 (12) |
C4 | 0.0285 (13) | 0.0418 (15) | 0.0357 (13) | −0.0005 (11) | 0.0028 (10) | 0.0046 (12) |
C5 | 0.0319 (14) | 0.0433 (15) | 0.0393 (14) | −0.0016 (12) | 0.0118 (11) | 0.0033 (12) |
C6 | 0.065 (2) | 0.062 (2) | 0.0253 (13) | −0.0115 (16) | 0.0055 (13) | −0.0008 (13) |
C7 | 0.0430 (15) | 0.0424 (15) | 0.0290 (14) | 0.0076 (13) | 0.0060 (11) | −0.0012 (12) |
C8 | 0.0321 (14) | 0.0374 (14) | 0.0268 (12) | −0.0042 (11) | 0.0024 (10) | −0.0016 (11) |
C9 | 0.0314 (13) | 0.0431 (15) | 0.0269 (12) | 0.0022 (12) | 0.0026 (10) | −0.0026 (12) |
C10 | 0.0294 (13) | 0.0412 (15) | 0.0251 (12) | −0.0046 (11) | 0.0012 (10) | −0.0030 (11) |
C11 | 0.0275 (12) | 0.0411 (14) | 0.0246 (12) | −0.0004 (11) | 0.0022 (10) | −0.0036 (11) |
C12 | 0.0272 (13) | 0.0393 (14) | 0.0265 (12) | −0.0009 (11) | 0.0025 (9) | −0.0022 (11) |
C13 | 0.0308 (13) | 0.0380 (14) | 0.0253 (12) | −0.0026 (11) | 0.0041 (10) | −0.0032 (11) |
C14 | 0.0263 (12) | 0.0378 (14) | 0.0260 (12) | 0.0021 (10) | 0.0030 (9) | 0.0001 (11) |
C15 | 0.0310 (13) | 0.0354 (14) | 0.0245 (12) | 0.0024 (11) | 0.0037 (10) | 0.0003 (10) |
C16 | 0.0340 (14) | 0.0326 (14) | 0.0277 (13) | 0.0054 (11) | 0.0061 (10) | 0.0002 (11) |
C17 | 0.0375 (14) | 0.0283 (12) | 0.0279 (12) | 0.0033 (11) | 0.0050 (10) | 0.0029 (11) |
C18 | 0.0447 (15) | 0.0281 (13) | 0.0270 (13) | 0.0069 (11) | 0.0078 (11) | 0.0012 (11) |
C19 | 0.0357 (14) | 0.0333 (13) | 0.0270 (13) | 0.0020 (11) | 0.0036 (10) | 0.0047 (11) |
C20 | 0.0359 (14) | 0.0392 (14) | 0.0296 (13) | 0.0070 (12) | 0.0008 (10) | 0.0052 (11) |
C21 | 0.0343 (14) | 0.0346 (13) | 0.0322 (13) | 0.0050 (11) | 0.0074 (10) | 0.0010 (11) |
C22 | 0.0520 (17) | 0.0611 (19) | 0.0234 (13) | −0.0051 (15) | 0.0041 (11) | −0.0045 (13) |
O1 | 0.0662 (15) | 0.0664 (15) | 0.0485 (13) | −0.0007 (13) | −0.0049 (11) | −0.0205 (13) |
O2 | 0.0565 (13) | 0.0432 (13) | 0.0536 (14) | 0.0068 (11) | −0.0016 (11) | −0.0204 (12) |
O3 | 0.0778 (15) | 0.0367 (12) | 0.0560 (13) | −0.0055 (11) | 0.0364 (12) | −0.0107 (11) |
O4 | 0.0577 (13) | 0.0309 (11) | 0.0463 (12) | −0.0036 (10) | 0.0217 (10) | −0.0080 (9) |
O5 | 0.0539 (12) | 0.0330 (11) | 0.0397 (11) | −0.0008 (10) | 0.0039 (9) | −0.0105 (10) |
O6 | 0.0789 (16) | 0.0460 (13) | 0.0349 (11) | 0.0130 (11) | 0.0050 (10) | −0.0038 (10) |
O7 | 0.0619 (13) | 0.0476 (13) | 0.0312 (11) | 0.0055 (10) | 0.0102 (9) | −0.0005 (10) |
N1—C1 | 1.330 (3) | C11—C12 | 1.523 (3) |
N1—N2 | 1.337 (3) | C11—H11A | 0.9900 |
N2—N3 | 1.321 (3) | C11—H11B | 0.9900 |
N3—N4 | 1.335 (3) | C12—C13 | 1.520 (3) |
N4—C1 | 1.334 (3) | C12—H12A | 0.9900 |
N5—N6 | 1.260 (3) | C12—H12B | 0.9900 |
N5—C1 | 1.405 (3) | C13—C14 | 1.518 (3) |
N6—C2 | 1.399 (3) | C13—H13A | 0.9900 |
N7—C2 | 1.335 (3) | C13—H13B | 0.9900 |
N7—N8 | 1.338 (3) | C14—C15 | 1.524 (3) |
N8—N9 | 1.324 (3) | C14—H14A | 0.9900 |
N9—N10 | 1.335 (3) | C14—H14B | 0.9900 |
N10—C2 | 1.333 (3) | C15—C16 | 1.514 (3) |
N11—C3 | 1.323 (3) | C15—H15A | 0.9900 |
N11—C4 | 1.373 (3) | C15—H15B | 0.9900 |
N11—C7 | 1.470 (3) | C16—C17 | 1.526 (3) |
N12—C3 | 1.326 (3) | C16—H16A | 0.9900 |
N12—C5 | 1.368 (3) | C16—H16B | 0.9900 |
N12—C6 | 1.468 (3) | C17—C18 | 1.512 (3) |
N13—C19 | 1.329 (3) | C17—H17A | 0.9900 |
N13—C20 | 1.370 (3) | C17—H17B | 0.9900 |
N13—C18 | 1.475 (3) | C18—H18A | 0.9900 |
N14—C19 | 1.330 (3) | C18—H18B | 0.9900 |
N14—C21 | 1.372 (3) | C19—H19 | 0.9500 |
N14—C22 | 1.466 (3) | C20—C21 | 1.342 (3) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.333 (3) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—H22A | 0.9800 |
C5—H5 | 0.9500 | C22—H22B | 0.9800 |
C6—H6A | 0.9800 | C22—H22C | 0.9800 |
C6—H6B | 0.9800 | O1—H11O | 0.87 (2) |
C6—H6C | 0.9800 | O1—H12O | 0.89 (3) |
C7—C8 | 1.515 (4) | O2—H21O | 0.82 (2) |
C7—H7A | 0.9900 | O2—H22O | 0.84 (3) |
C7—H7B | 0.9900 | O3—H31O | 0.84 (2) |
C8—C9 | 1.517 (3) | O3—H32O | 0.85 (3) |
C8—H8A | 0.9900 | O4—H41O | 0.87 (2) |
C8—H8B | 0.9900 | O4—H42O | 0.85 (2) |
C9—C10 | 1.515 (4) | O5—H51O | 0.87 (2) |
C9—H9A | 0.9900 | O5—H52O | 0.82 (2) |
C9—H9B | 0.9900 | O6—H61O | 0.90 (2) |
C10—C11 | 1.522 (3) | O6—H62O | 0.84 (2) |
C10—H10A | 0.9900 | O7—H71O | 0.86 (3) |
C10—H10B | 0.9900 | O7—H72O | 0.84 (2) |
C1—N1—N2 | 104.39 (19) | C12—C11—H11A | 108.6 |
N3—N2—N1 | 109.03 (19) | C10—C11—H11B | 108.6 |
N2—N3—N4 | 110.2 (2) | C12—C11—H11B | 108.6 |
C1—N4—N3 | 103.69 (19) | H11A—C11—H11B | 107.6 |
N6—N5—C1 | 112.44 (18) | C13—C12—C11 | 113.0 (2) |
N5—N6—C2 | 112.98 (18) | C13—C12—H12A | 109.0 |
C2—N7—N8 | 103.75 (19) | C11—C12—H12A | 109.0 |
N9—N8—N7 | 110.2 (2) | C13—C12—H12B | 109.0 |
N8—N9—N10 | 108.86 (19) | C11—C12—H12B | 109.0 |
C2—N10—N9 | 104.76 (18) | H12A—C12—H12B | 107.8 |
C3—N11—C4 | 108.4 (2) | C14—C13—C12 | 114.7 (2) |
C3—N11—C7 | 125.9 (2) | C14—C13—H13A | 108.6 |
C4—N11—C7 | 125.75 (19) | C12—C13—H13A | 108.6 |
C3—N12—C5 | 108.1 (2) | C14—C13—H13B | 108.6 |
C3—N12—C6 | 126.3 (2) | C12—C13—H13B | 108.6 |
C5—N12—C6 | 125.6 (2) | H13A—C13—H13B | 107.6 |
C19—N13—C20 | 108.58 (19) | C13—C14—C15 | 112.9 (2) |
C19—N13—C18 | 125.8 (2) | C13—C14—H14A | 109.0 |
C20—N13—C18 | 125.6 (2) | C15—C14—H14A | 109.0 |
C19—N14—C21 | 108.55 (19) | C13—C14—H14B | 109.0 |
C19—N14—C22 | 125.8 (2) | C15—C14—H14B | 109.0 |
C21—N14—C22 | 125.6 (2) | H14A—C14—H14B | 107.8 |
N1—C1—N4 | 112.7 (2) | C16—C15—C14 | 114.4 (2) |
N1—C1—N5 | 119.4 (2) | C16—C15—H15A | 108.7 |
N4—C1—N5 | 127.95 (19) | C14—C15—H15A | 108.7 |
N10—C2—N7 | 112.4 (2) | C16—C15—H15B | 108.7 |
N10—C2—N6 | 119.17 (19) | C14—C15—H15B | 108.7 |
N7—C2—N6 | 128.38 (19) | H15A—C15—H15B | 107.6 |
N11—C3—N12 | 108.7 (2) | C15—C16—C17 | 112.3 (2) |
N11—C3—H3 | 125.6 | C15—C16—H16A | 109.1 |
N12—C3—H3 | 125.6 | C17—C16—H16A | 109.1 |
C5—C4—N11 | 107.1 (2) | C15—C16—H16B | 109.1 |
C5—C4—H4 | 126.5 | C17—C16—H16B | 109.1 |
N11—C4—H4 | 126.5 | H16A—C16—H16B | 107.9 |
C4—C5—N12 | 107.7 (2) | C18—C17—C16 | 111.7 (2) |
C4—C5—H5 | 126.2 | C18—C17—H17A | 109.3 |
N12—C5—H5 | 126.2 | C16—C17—H17A | 109.3 |
N12—C6—H6A | 109.5 | C18—C17—H17B | 109.3 |
N12—C6—H6B | 109.5 | C16—C17—H17B | 109.3 |
H6A—C6—H6B | 109.5 | H17A—C17—H17B | 107.9 |
N12—C6—H6C | 109.5 | N13—C18—C17 | 112.2 (2) |
H6A—C6—H6C | 109.5 | N13—C18—H18A | 109.2 |
H6B—C6—H6C | 109.5 | C17—C18—H18A | 109.2 |
N11—C7—C8 | 112.2 (2) | N13—C18—H18B | 109.2 |
N11—C7—H7A | 109.2 | C17—C18—H18B | 109.2 |
C8—C7—H7A | 109.2 | H18A—C18—H18B | 107.9 |
N11—C7—H7B | 109.2 | N13—C19—N14 | 108.4 (2) |
C8—C7—H7B | 109.2 | N13—C19—H19 | 125.8 |
H7A—C7—H7B | 107.9 | N14—C19—H19 | 125.8 |
C7—C8—C9 | 111.5 (2) | C21—C20—N13 | 107.3 (2) |
C7—C8—H8A | 109.3 | C21—C20—H20 | 126.3 |
C9—C8—H8A | 109.3 | N13—C20—H20 | 126.3 |
C7—C8—H8B | 109.3 | C20—C21—N14 | 107.2 (2) |
C9—C8—H8B | 109.3 | C20—C21—H21 | 126.4 |
H8A—C8—H8B | 108.0 | N14—C21—H21 | 126.4 |
C10—C9—C8 | 113.4 (2) | N14—C22—H22A | 109.5 |
C10—C9—H9A | 108.9 | N14—C22—H22B | 109.5 |
C8—C9—H9A | 108.9 | H22A—C22—H22B | 109.5 |
C10—C9—H9B | 108.9 | N14—C22—H22C | 109.5 |
C8—C9—H9B | 108.9 | H22A—C22—H22C | 109.5 |
H9A—C9—H9B | 107.7 | H22B—C22—H22C | 109.5 |
C9—C10—C11 | 113.6 (2) | H11O—O1—H12O | 108 (4) |
C9—C10—H10A | 108.8 | H21O—O2—H22O | 111 (4) |
C11—C10—H10A | 108.8 | H31O—O3—H32O | 111 (4) |
C9—C10—H10B | 108.8 | H41O—O4—H42O | 103 (3) |
C11—C10—H10B | 108.8 | H51O—O5—H52O | 106 (4) |
H10A—C10—H10B | 107.7 | H61O—O6—H62O | 105 (3) |
C10—C11—C12 | 114.6 (2) | H71O—O7—H72O | 113 (4) |
C10—C11—H11A | 108.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11O···N2i | 0.87 (3) | 2.02 (3) | 2.884 (3) | 174 (3) |
O1—H12O···O2 | 0.89 (5) | 2.00 (4) | 2.850 (3) | 159 (4) |
O2—H22O···O3 | 0.84 (4) | 2.00 (4) | 2.819 (3) | 162 (4) |
O2—H21O···N1 | 0.82 (3) | 2.06 (3) | 2.875 (3) | 174 (3) |
O3—H32O···N3ii | 0.85 (4) | 2.00 (4) | 2.853 (3) | 172 (4) |
O3—H31O···N7 | 0.84 (4) | 2.14 (3) | 2.959 (3) | 165 (4) |
O4—H42O···N4ii | 0.86 (3) | 2.06 (3) | 2.914 (3) | 175 (3) |
O4—H41O···N8 | 0.87 (3) | 1.99 (3) | 2.853 (3) | 171 (3) |
O5—H52O···N10ii | 0.82 (3) | 2.06 (3) | 2.879 (3) | 179 (3) |
O5—H51O···O4 | 0.87 (3) | 1.94 (3) | 2.790 (3) | 166 (4) |
O6—H61O···O5 | 0.90 (3) | 1.89 (3) | 2.755 (3) | 161 (3) |
O6—H62O···O7 | 0.84 (4) | 1.93 (3) | 2.753 (3) | 169 (3) |
O7—H71O···O6iii | 0.86 (3) | 1.96 (3) | 2.807 (4) | 169 (4) |
O7—H72O···N9iv | 0.84 (3) | 2.10 (3) | 2.931 (3) | 170 (3) |
Symmetry codes: (i) −x+2, y−1/2, −z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1. |
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