The crystal structures of the solid form of solvated 2,6-bis(1H-imidazol-2-yl)pyridine (H2dimpy) trihydrate, C11H9N5·3H2O·[+solvent], I, and its hydrate hydrochloride salt 2-[6-(1H-imidazol-2-yl)pyridin-2-yl]-1H-imidazol-3-ium chloride trihydrate, C11H10N5+·Cl−·3H2O, II, are reported and analysed in detail, along with potentiometric and spectrophotometric titrations for evaluation of the acid–base equilibria and proton-coupled electron-transfer reactions. Compound I crystallizes in the high-symmetry trigonal space group P3221 with an atypical formation of solvent-accessible voids, as a consequence of the 32 screw axis in the crystallographic c-axis direction, which are probably occupied by uncharacterized disordered solvent molecules. Additionally, the trihydrated chloride salt crystallizes in the conventional monoclinic space group P21/c without the formation of solvent-accessible voids. The acid–base equilibria of H2dimpy were studied by potentiometric and spectrophotometric titrations, and the results suggest the formation of H3dimpy+ (pKa1 = 5.40) and H4dimpy2+ (pKa2 = 3.98), with the electrochemical behaviour of these species showing two consecutive irreversible proton-coupled electron-transfer reactions. Density functional theory (DFT) calculations corroborate the interpretation of the experimental results and support the assignment of the electrochemical behaviour.
Supporting information
CCDC references: 1915852; 1915851
For both structures, data collection: APEX3 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008).
2,6-Bis(1
H-imidazol-2-yl)pyridine trihydrate (H2dimpyI)
top
Crystal data top
C11H9N5·3H2O·[+solvent] | Dx = 1.127 Mg m−3 |
Mr = 265.28 | Cu Kα radiation, λ = 1.54178 Å |
Trigonal, P3221 | Cell parameters from 3604 reflections |
a = 18.6043 (5) Å | θ = 2.7–68.5° |
c = 3.9112 (1) Å | µ = 0.71 mm−1 |
V = 1172.38 (7) Å3 | T = 150 K |
Z = 3 | Needle, colourless |
F(000) = 420 | 0.42 × 0.07 × 0.06 mm |
Data collection top
Bruker APEX CCD detector diffractometer | 1416 independent reflections |
Radiation source: fine-focus sealed tube | 1375 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.035 |
φ and ω scans | θmax = 68.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −22→22 |
Tmin = 0.589, Tmax = 0.753 | k = −21→11 |
4574 measured reflections | l = −4→4 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.0039P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.19 e Å−3 |
1416 reflections | Δρmin = −0.18 e Å−3 |
107 parameters | Absolute structure: Flack x determined using 610 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
13 restraints | Absolute structure parameter: −0.06 (13) |
Primary atom site location: dual | |
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) |
C1 | 0.82009 (12) | 0.40541 (14) | 0.3290 (4) | 0.0424 (5) | |
H1 | 0.810118 | 0.449603 | 0.278080 | 0.051* | |
C2 | 0.77089 (11) | 0.32375 (13) | 0.2485 (4) | 0.0439 (5) | |
H2 | 0.719764 | 0.301261 | 0.128372 | 0.053* | |
C3 | 0.87644 (11) | 0.33371 (12) | 0.5186 (4) | 0.0376 (4) | |
C4 | 0.93872 (11) | 0.31921 (12) | 0.6842 (4) | 0.0393 (5) | |
C5 | 0.93498 (13) | 0.24231 (13) | 0.6823 (5) | 0.0488 (5) | |
H5 | 0.889499 | 0.195000 | 0.581093 | 0.059* | |
C6 | 1.000000 | 0.23727 (18) | 0.833333 | 0.0563 (7) | |
H6 | 1.000000 | 0.186204 | 0.833331 | 0.068* | |
N1 | 0.88686 (9) | 0.41061 (10) | 0.4985 (3) | 0.0371 (4) | |
H1A | 0.929205 | 0.456226 | 0.580214 | 0.045* | |
N2 | 0.80616 (10) | 0.27824 (10) | 0.3670 (4) | 0.0434 (4) | |
N3 | 1.000000 | 0.38611 (12) | 0.833333 | 0.0357 (5) | |
O1 | 1.000000 | 0.56592 (11) | 0.833333 | 0.0498 (5) | |
H1B | 0.984190 | 0.590942 | 0.977527 | 0.075* | |
O2B | 0.7265 (2) | 0.1091 (2) | 0.420 (4) | 0.126 (4) | 0.710 (16) |
H2BA | 0.753917 | 0.088908 | 0.317271 | 0.189* | 0.710 (16) |
H2BB | 0.762778 | 0.161343 | 0.450509 | 0.189* | 0.710 (16) |
O2A | 0.7301 (4) | 0.1159 (4) | 0.160 (3) | 0.059 (3) | 0.290 (16) |
H2AA | 0.735540 | 0.091151 | −0.018624 | 0.089* | 0.290 (16) |
H2AB | 0.770014 | 0.167082 | 0.141571 | 0.089* | 0.290 (16) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0340 (9) | 0.0561 (12) | 0.0319 (7) | 0.0187 (9) | 0.0036 (6) | 0.0041 (7) |
C2 | 0.0340 (9) | 0.0572 (12) | 0.0333 (8) | 0.0175 (8) | 0.0007 (6) | −0.0024 (7) |
C3 | 0.0302 (8) | 0.0444 (9) | 0.0303 (8) | 0.0126 (7) | 0.0070 (6) | −0.0016 (6) |
C4 | 0.0334 (9) | 0.0448 (10) | 0.0336 (8) | 0.0150 (8) | 0.0094 (7) | 0.0010 (7) |
C5 | 0.0433 (12) | 0.0431 (10) | 0.0536 (11) | 0.0167 (9) | 0.0053 (9) | −0.0019 (8) |
C6 | 0.0581 (18) | 0.0482 (11) | 0.0658 (17) | 0.0291 (9) | 0.0001 (14) | 0.0001 (7) |
N1 | 0.0275 (7) | 0.0437 (8) | 0.0320 (6) | 0.0117 (6) | 0.0047 (5) | 0.0009 (6) |
N2 | 0.0343 (7) | 0.0484 (9) | 0.0364 (7) | 0.0122 (7) | 0.0029 (5) | −0.0061 (6) |
N3 | 0.0298 (10) | 0.0420 (9) | 0.0312 (9) | 0.0149 (5) | 0.0072 (7) | 0.0036 (3) |
O1 | 0.0377 (10) | 0.0433 (8) | 0.0665 (13) | 0.0189 (5) | −0.0007 (8) | −0.0004 (4) |
O2B | 0.0570 (19) | 0.0463 (17) | 0.261 (13) | 0.0153 (14) | −0.052 (4) | −0.027 (3) |
O2A | 0.049 (3) | 0.040 (3) | 0.084 (6) | 0.019 (2) | −0.024 (3) | −0.014 (3) |
Geometric parameters (Å, º) top
C1—H1 | 0.9500 | C5—H5 | 0.9500 |
C1—C2 | 1.362 (3) | C5—C6 | 1.391 (3) |
C1—N1 | 1.368 (3) | C6—H6 | 0.9500 |
C2—H2 | 0.9500 | N1—H1A | 0.8800 |
C2—N2 | 1.385 (3) | O1—H1Bi | 0.87 |
C3—C4 | 1.465 (3) | O1—H1B | 0.8708 |
C3—N1 | 1.347 (3) | O2B—H2BA | 0.8693 |
C3—N2 | 1.333 (3) | O2B—H2BB | 0.8699 |
C4—C5 | 1.397 (3) | O2A—H2AA | 0.8711 |
C4—N3 | 1.330 (2) | O2A—H2AB | 0.8700 |
| | | |
C2—C1—H1 | 127.1 | C6—C5—C4 | 117.8 (2) |
C2—C1—N1 | 105.72 (18) | C6—C5—H5 | 121.1 |
N1—C1—H1 | 127.1 | C5i—C6—C5 | 119.7 (3) |
C1—C2—H2 | 124.9 | C5i—C6—H6 | 120.2 |
C1—C2—N2 | 110.18 (16) | C5—C6—H6 | 120.2 |
N2—C2—H2 | 124.9 | C1—N1—H1A | 126.0 |
N1—C3—C4 | 120.95 (17) | C3—N1—C1 | 108.06 (16) |
N2—C3—C4 | 127.88 (18) | C3—N1—H1A | 126.0 |
N2—C3—N1 | 111.15 (18) | C3—N2—C2 | 104.88 (16) |
C5—C4—C3 | 123.15 (18) | C4—N3—C4i | 119.1 (2) |
N3—C4—C3 | 114.09 (18) | H1B—O1—H1Bi | 90.6 |
N3—C4—C5 | 122.75 (18) | H2BA—O2B—H2BB | 104.6 |
C4—C5—H5 | 121.1 | H2AA—O2A—H2AB | 104.4 |
| | | |
C1—C2—N2—C3 | 0.12 (19) | N1—C1—C2—N2 | 0.22 (19) |
C2—C1—N1—C3 | −0.47 (17) | N1—C3—C4—C5 | −173.49 (15) |
C3—C4—C5—C6 | 176.78 (13) | N1—C3—C4—N3 | 5.7 (2) |
C3—C4—N3—C4i | −177.97 (15) | N1—C3—N2—C2 | −0.43 (17) |
C4—C3—N1—C1 | 179.33 (14) | N2—C3—C4—C5 | 5.0 (3) |
C4—C3—N2—C2 | −179.08 (15) | N2—C3—C4—N3 | −175.81 (13) |
C4—C5—C6—C5i | 1.07 (11) | N2—C3—N1—C1 | 0.58 (17) |
C5—C4—N3—C4i | 1.18 (12) | N3—C4—C5—C6 | −2.3 (2) |
Symmetry code: (i) −x+2, −x+y+1, −z+5/3. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.88 | 2.05 | 2.900 (2) | 163 |
O1—H1B···O2Bii | 0.87 | 2.07 | 2.823 (5) | 144 |
O1—H1B···O2Aii | 0.87 | 2.19 | 2.719 (7) | 119 |
O2B—H2BB···N2 | 0.87 | 1.93 | 2.734 (4) | 153 |
O2A—H2AB···N2 | 0.87 | 2.03 | 2.740 (7) | 138 |
Symmetry code: (ii) −y+1, x−y, z+2/3. |
2-[6-(1
H-Imidazol-2-yl)pyridin-2-yl]-1
H-imidazol-3-ium chloride
trihydrate (II)
top
Crystal data top
C11H10N5+·Cl−·3H2O | F(000) = 632 |
Mr = 301.74 | Dx = 1.404 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 6.6577 (5) Å | Cell parameters from 51 reflections |
b = 22.6308 (16) Å | θ = 2.4–19.1° |
c = 9.7566 (7) Å | µ = 2.53 mm−1 |
β = 103.845 (3)° | T = 150 K |
V = 1427.31 (18) Å3 | Needle, colorless |
Z = 4 | 0.21 × 0.12 × 0.06 mm |
Data collection top
Bruker APEX CCD detector diffractometer | 2337 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.037 |
phi and ω scans | θmax = 66.6°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −7→7 |
Tmin = 0.541, Tmax = 0.753 | k = −26→26 |
12948 measured reflections | l = −10→11 |
2501 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.3908P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2501 reflections | Δρmax = 0.19 e Å−3 |
208 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | |
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 | |
Cl1 | 0.12492 (5) | 0.11289 (2) | 0.19035 (3) | 0.02985 (13) | |
N1 | 0.23324 (18) | 0.15345 (5) | 0.50852 (13) | 0.0242 (3) | |
H1 | 0.209 (3) | 0.1367 (8) | 0.4320 (19) | 0.029* | |
N2 | 0.32601 (18) | 0.16788 (5) | 0.73294 (13) | 0.0238 (3) | |
H2 | 0.363 (2) | 0.1621 (8) | 0.8221 (19) | 0.029* | |
N3 | 0.25814 (16) | 0.03224 (5) | 0.52905 (12) | 0.0207 (2) | |
N4 | 0.16978 (18) | −0.02797 (6) | 0.27592 (13) | 0.0264 (3) | |
H4 | 0.164 (3) | 0.0095 (8) | 0.2606 (19) | 0.032* | |
N5 | 0.21873 (18) | −0.11532 (5) | 0.38022 (14) | 0.0284 (3) | |
C1 | 0.2362 (2) | 0.21322 (6) | 0.52931 (16) | 0.0301 (3) | |
H1A | 0.202959 | 0.242704 | 0.458158 | 0.036* | |
C2 | 0.2952 (2) | 0.22247 (6) | 0.66969 (16) | 0.0292 (3) | |
H2A | 0.312323 | 0.259679 | 0.716116 | 0.035* | |
C3 | 0.28748 (19) | 0.12627 (6) | 0.63302 (14) | 0.0211 (3) | |
C4 | 0.29992 (18) | 0.06222 (6) | 0.65134 (14) | 0.0203 (3) | |
C5 | 0.3499 (2) | 0.03559 (6) | 0.78353 (15) | 0.0253 (3) | |
H5 | 0.377869 | 0.058487 | 0.867563 | 0.030* | |
C6 | 0.3575 (2) | −0.02556 (6) | 0.78827 (16) | 0.0293 (3) | |
H6 | 0.390061 | −0.045476 | 0.876542 | 0.035* | |
C7 | 0.3175 (2) | −0.05737 (6) | 0.66416 (15) | 0.0271 (3) | |
H7 | 0.324146 | −0.099307 | 0.665627 | 0.032* | |
C8 | 0.26720 (19) | −0.02676 (6) | 0.53637 (15) | 0.0217 (3) | |
C9 | 0.21986 (19) | −0.05725 (6) | 0.40025 (15) | 0.0231 (3) | |
C10 | 0.1339 (2) | −0.06927 (7) | 0.17056 (16) | 0.0316 (3) | |
H10 | 0.095412 | −0.062150 | 0.071766 | 0.038* | |
C11 | 0.1645 (2) | −0.12247 (7) | 0.23613 (17) | 0.0326 (4) | |
H11 | 0.150535 | −0.159532 | 0.189061 | 0.039* | |
O1 | 0.70136 (19) | 0.21532 (5) | 0.43975 (13) | 0.0386 (3) | |
H1B | 0.726 (3) | 0.2432 (10) | 0.503 (2) | 0.058* | |
H1C | 0.728 (3) | 0.1862 (10) | 0.494 (2) | 0.058* | |
O2 | 0.4310 (2) | 0.14867 (5) | 0.01164 (11) | 0.0345 (3) | |
H2B | 0.344 (3) | 0.1399 (9) | 0.064 (2) | 0.052* | |
H2C | 0.531 (3) | 0.1656 (10) | 0.063 (2) | 0.052* | |
O3 | 0.76769 (18) | 0.20389 (5) | 0.17490 (12) | 0.0348 (3) | |
H3A | 0.868 (3) | 0.1834 (10) | 0.182 (2) | 0.052* | |
H3B | 0.756 (3) | 0.2116 (9) | 0.259 (2) | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0355 (2) | 0.0303 (2) | 0.0229 (2) | 0.00122 (13) | 0.00543 (15) | 0.00105 (13) |
N1 | 0.0294 (6) | 0.0225 (6) | 0.0205 (6) | −0.0018 (5) | 0.0054 (5) | −0.0005 (5) |
N2 | 0.0294 (6) | 0.0204 (6) | 0.0220 (6) | −0.0016 (4) | 0.0067 (5) | −0.0017 (5) |
N3 | 0.0171 (5) | 0.0209 (6) | 0.0236 (6) | −0.0005 (4) | 0.0040 (4) | −0.0009 (4) |
N4 | 0.0261 (6) | 0.0254 (6) | 0.0267 (6) | −0.0006 (5) | 0.0042 (5) | −0.0039 (5) |
N5 | 0.0262 (6) | 0.0233 (6) | 0.0360 (7) | −0.0026 (4) | 0.0076 (5) | −0.0072 (5) |
C1 | 0.0390 (8) | 0.0205 (7) | 0.0318 (8) | −0.0010 (6) | 0.0107 (6) | 0.0046 (6) |
C2 | 0.0387 (8) | 0.0181 (7) | 0.0329 (8) | −0.0027 (6) | 0.0128 (6) | −0.0016 (6) |
C3 | 0.0180 (6) | 0.0233 (7) | 0.0224 (7) | −0.0008 (5) | 0.0055 (5) | −0.0009 (5) |
C4 | 0.0155 (6) | 0.0215 (7) | 0.0235 (7) | −0.0002 (5) | 0.0041 (5) | −0.0016 (5) |
C5 | 0.0258 (7) | 0.0257 (7) | 0.0227 (7) | 0.0008 (5) | 0.0026 (5) | −0.0009 (6) |
C6 | 0.0341 (8) | 0.0262 (7) | 0.0258 (7) | 0.0018 (6) | 0.0035 (6) | 0.0054 (6) |
C7 | 0.0286 (7) | 0.0198 (6) | 0.0312 (8) | 0.0008 (5) | 0.0042 (6) | 0.0012 (6) |
C8 | 0.0151 (6) | 0.0219 (7) | 0.0280 (7) | −0.0009 (5) | 0.0050 (5) | −0.0022 (5) |
C9 | 0.0177 (6) | 0.0228 (6) | 0.0284 (7) | −0.0015 (5) | 0.0049 (5) | −0.0025 (6) |
C10 | 0.0289 (8) | 0.0388 (9) | 0.0264 (8) | −0.0030 (6) | 0.0051 (6) | −0.0106 (6) |
C11 | 0.0284 (7) | 0.0308 (8) | 0.0381 (9) | −0.0041 (6) | 0.0071 (7) | −0.0148 (7) |
O1 | 0.0539 (7) | 0.0298 (6) | 0.0310 (6) | 0.0030 (5) | 0.0083 (5) | −0.0031 (5) |
O2 | 0.0469 (7) | 0.0338 (6) | 0.0238 (5) | −0.0080 (5) | 0.0101 (5) | −0.0031 (4) |
O3 | 0.0395 (6) | 0.0338 (6) | 0.0305 (6) | 0.0071 (5) | 0.0073 (5) | 0.0053 (5) |
Geometric parameters (Å, º) top
N1—H1 | 0.818 (18) | C4—C5 | 1.3899 (19) |
N1—C1 | 1.3672 (18) | C5—H5 | 0.9500 |
N1—C3 | 1.3321 (18) | C5—C6 | 1.385 (2) |
N2—H2 | 0.856 (18) | C6—H6 | 0.9500 |
N2—C2 | 1.3742 (19) | C6—C7 | 1.379 (2) |
N2—C3 | 1.3354 (18) | C7—H7 | 0.9500 |
N3—C4 | 1.3426 (17) | C7—C8 | 1.395 (2) |
N3—C8 | 1.3376 (17) | C8—C9 | 1.4625 (19) |
N4—H4 | 0.861 (19) | C10—H10 | 0.9500 |
N4—C9 | 1.3521 (19) | C10—C11 | 1.356 (2) |
N4—C10 | 1.3674 (19) | C11—H11 | 0.9500 |
N5—C9 | 1.3286 (18) | O1—H1B | 0.87 (2) |
N5—C11 | 1.375 (2) | O1—H1C | 0.84 (2) |
C1—H1A | 0.9500 | O2—H2B | 0.88 (2) |
C1—C2 | 1.348 (2) | O2—H2C | 0.82 (2) |
C2—H2A | 0.9500 | O3—H3A | 0.80 (2) |
C3—C4 | 1.4604 (18) | O3—H3B | 0.86 (2) |
| | | |
C1—N1—H1 | 125.9 (12) | C6—C5—C4 | 117.58 (13) |
C3—N1—H1 | 124.8 (12) | C6—C5—H5 | 121.2 |
C3—N1—C1 | 109.29 (12) | C5—C6—H6 | 120.2 |
C2—N2—H2 | 124.7 (12) | C7—C6—C5 | 119.63 (13) |
C3—N2—H2 | 126.3 (12) | C7—C6—H6 | 120.2 |
C3—N2—C2 | 108.91 (12) | C6—C7—H7 | 120.7 |
C8—N3—C4 | 117.38 (12) | C6—C7—C8 | 118.69 (13) |
C9—N4—H4 | 129.1 (12) | C8—C7—H7 | 120.7 |
C9—N4—C10 | 107.50 (13) | N3—C8—C7 | 122.78 (13) |
C10—N4—H4 | 123.4 (12) | N3—C8—C9 | 115.17 (12) |
C9—N5—C11 | 104.94 (12) | C7—C8—C9 | 122.05 (12) |
N1—C1—H1A | 126.4 | N4—C9—C8 | 122.47 (12) |
C2—C1—N1 | 107.14 (13) | N5—C9—N4 | 111.18 (12) |
C2—C1—H1A | 126.4 | N5—C9—C8 | 126.35 (13) |
N2—C2—H2A | 126.5 | N4—C10—H10 | 127.1 |
C1—C2—N2 | 107.02 (12) | C11—C10—N4 | 105.83 (14) |
C1—C2—H2A | 126.5 | C11—C10—H10 | 127.1 |
N1—C3—N2 | 107.63 (12) | N5—C11—H11 | 124.7 |
N1—C3—C4 | 124.40 (12) | C10—C11—N5 | 110.55 (13) |
N2—C3—C4 | 127.97 (12) | C10—C11—H11 | 124.7 |
N3—C4—C3 | 113.53 (12) | H1B—O1—H1C | 99 (2) |
N3—C4—C5 | 123.93 (12) | H2B—O2—H2C | 107 (2) |
C5—C4—C3 | 122.54 (12) | H3A—O3—H3B | 107 (2) |
C4—C5—H5 | 121.2 | | |
| | | |
N1—C1—C2—N2 | −0.46 (17) | C4—N3—C8—C7 | 0.00 (19) |
N1—C3—C4—N3 | 2.26 (18) | C4—N3—C8—C9 | 179.85 (11) |
N1—C3—C4—C5 | −177.58 (12) | C4—C5—C6—C7 | 0.5 (2) |
N2—C3—C4—N3 | −177.85 (12) | C5—C6—C7—C8 | −0.9 (2) |
N2—C3—C4—C5 | 2.3 (2) | C6—C7—C8—N3 | 0.7 (2) |
N3—C4—C5—C6 | 0.3 (2) | C6—C7—C8—C9 | −179.12 (12) |
N3—C8—C9—N4 | −0.23 (18) | C7—C8—C9—N4 | 179.61 (13) |
N3—C8—C9—N5 | 179.97 (12) | C7—C8—C9—N5 | −0.2 (2) |
N4—C10—C11—N5 | 0.03 (16) | C8—N3—C4—C3 | 179.65 (11) |
C1—N1—C3—N2 | −0.29 (15) | C8—N3—C4—C5 | −0.51 (18) |
C1—N1—C3—C4 | 179.62 (12) | C9—N4—C10—C11 | −0.15 (15) |
C2—N2—C3—N1 | 0.00 (15) | C9—N5—C11—C10 | 0.10 (16) |
C2—N2—C3—C4 | −179.91 (13) | C10—N4—C9—N5 | 0.22 (15) |
C3—N1—C1—C2 | 0.48 (17) | C10—N4—C9—C8 | −179.60 (12) |
C3—N2—C2—C1 | 0.29 (16) | C11—N5—C9—N4 | −0.20 (15) |
C3—C4—C5—C6 | −179.91 (12) | C11—N5—C9—C8 | 179.62 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.82 (2) | 2.35 (2) | 3.1508 (13) | 166 (2) |
N2—H2···O2i | 0.86 (2) | 1.82 (2) | 2.6762 (17) | 178 (2) |
N4—H4···Cl1 | 0.86 (2) | 2.43 (2) | 3.2907 (13) | 174 (2) |
O1—H1B···O3ii | 0.87 (2) | 2.03 (2) | 2.8839 (16) | 169 (2) |
O1—H1C···N5iii | 0.84 (2) | 2.00 (2) | 2.8359 (18) | 178 (2) |
O2—H2B···Cl1 | 0.88 (2) | 2.21 (2) | 3.0900 (13) | 177 (2) |
O2—H2C···O3 | 0.82 (2) | 1.90 (2) | 2.7230 (17) | 177 (2) |
O3—H3A···Cl1iv | 0.80 (2) | 2.33 (2) | 3.1223 (12) | 171 (2) |
O3—H3B···O1 | 0.86 (2) | 1.89 (2) | 2.7359 (17) | 169 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z. |