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The organic–inorganic hybrid compound 4-aminopyridinium tetraaquabis(sulfato)iron(III), (C
5H
7N
2)[Fe
III(H
2O)
4(SO
4)
2] (4apFeS), was obtained by slow evaporation of the solvent at room temperature and characterized by single-crystal X-ray diffraction in the temperature range from 290 to 80 K. Differential scanning calorimetry revealed that the title compound undergoes a sequence of three reversible phase transitions, which has been verified by variable-temperature X-ray diffraction analysis during cooling–heating cycles over the temperature ranges 290–100–290 K. In the room-temperature phase (I), space group
C2/
c, oxygen atoms from the closest Fe-atom environment (octahedral) were disordered over two equivalent positions around a twofold axis. Two intermediate phases (II), (III) were solved and refined as incommensurately modulated structures, employing the superspace formalism applied to single-crystal X-ray diffraction data. Both structures can be described in the (3+1)-dimensional monoclinic
X2/
c(α,0,γ)0
s superspace group (where
X is ½, ½, 0, ½) with modulation wavevectors
q = (0.2943, 0, 0.5640) and
q = (0.3366, 0, 0.5544) for phases (II) and (III), respectively. The completely ordered low-temperature phase (IV) was refined with the twinning model in the triclinic
P space group, revealing the existence of two domains. The dynamics of the disordered anionic substructure in the 4apFeS crystal seems to play an essential role in the phase transition mechanisms. The discrete organic moieties were found to be fully ordered even at room temperature.
Supporting information
B-IncStrDB reference: 15592EoXXcr
CCDC references: 1960573; 1960574; 1960575
Data collection: CrysAlis PRO 1.171.39.12b (Rigaku OD, 2015) for PhaseII, PhaseIII; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for PhaseIV. Cell refinement: CrysAlis PRO 1.171.39.12b (Rigaku OD, 2015) for PhaseII, PhaseIII; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for PhaseIV. Data reduction: CrysAlis PRO 1.171.39.12b (Rigaku OD, 2015) for PhaseII, PhaseIII; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for PhaseIV. Program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2015) for PhaseIV. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for PhaseIV. Molecular graphics: Diamond 2.1c (Brandenburg, 1997) for PhaseIV. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for PhaseIV.
Crystal data top
FeS2O12N2C5H15 | Z = 4 |
Mr = 415.1 | F(000) = 852 |
Monoclinic, X2/c(α0γ)0s† | Dx = 1.974 Mg m−3 |
q = 0.294300a* + 0.564000c* | Mo Kα radiation, λ = 0.71073 Å |
a = 12.1601 (3) Å | Cell parameters from 6734 reflections |
b = 17.2511 (3) Å | θ = 3.4–29.3° |
c = 6.7758 (2) Å | µ = 1.45 mm−1 |
β = 100.715 (2)° | T = 245 K |
V = 1396.61 (6) Å3 | 0.51 × 0.44 × 0.30 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, x2, −x3+1/2, −x4+1/2; (3) −x1, −x2, −x3, −x4; (4) x1, −x2, x3+1/2, x4+1/2; (5) x1+1/2, x2+1/2, x3, x4+1/2; (6) −x1+1/2, x2+1/2, −x3+1/2, −x4; (7) −x1+1/2, −x2+1/2, −x3, −x4+1/2; (8) x1+1/2, −x2+1/2, x3+1/2, x4.
|
Data collection top
Xcalibur, Atlas diffractometer | 5303 independent reflections |
Radiation source: X-ray tube | 2856 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.6249 pixels mm-1 | θmax = 29.6°, θmin = 3.0° |
ω scans | h = −16→17 |
Absorption correction: analytical CrysAlisPro 1.171.39.12b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −23→22 |
Tmin = 0.586, Tmax = 0.751 | l = −9→9 |
23230 measured reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
wR(F2) = 0.089 | (Δ/σ)max = 3.804 |
S = 1.34 | Δρmax = 1.24 e Å−3 |
5303 reflections | Δρmin = −0.61 e Å−3 |
384 parameters | Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction coefficient: 5408.21 |
41 constraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.5 | 0.356897 (15) | 0.25 | 0.01310 (9) | |
S1 | 0.33286 (3) | 0.351013 (19) | −0.19593 (5) | 0.01402 (11) | |
O2s | 0.22908 (8) | 0.34282 (6) | −0.11998 (17) | 0.0264 (4) | |
O4s | 0.33393 (13) | 0.42245 (6) | −0.3114 (2) | 0.0277 (4) | |
O3s | 0.35027 (13) | 0.28467 (7) | −0.3189 (2) | 0.0258 (7) | |
O6w | 0.6044 (2) | 0.27668 (14) | 0.1791 (4) | 0.0317 (9) | |
O5w1 | 0.5921 (7) | 0.4411 (3) | 0.1541 (10) | 0.0516 (12) | 0.5 |
O5w2 | 0.6067 (6) | 0.4360 (3) | 0.1756 (8) | 0.0213 (10) | 0.5 |
N1 | 0.5 | 0.08806 (12) | 0.25 | 0.0280 (8) | |
O1b1 | 0.4271 (5) | 0.3484 (4) | −0.0265 (8) | 0.0204 (8) | 0.5 |
O1b2 | 0.4281 (5) | 0.3630 (5) | −0.0241 (8) | 0.045 (2) | 0.5 |
N2 | 0.5 | −0.14851 (10) | 0.25 | 0.0282 (7) | |
C1 | 0.5 | 0.01091 (12) | 0.25 | 0.0200 (6) | |
C2 | 0.39963 (12) | −0.03151 (9) | 0.2237 (2) | 0.0267 (5) | |
C3 | 0.40199 (13) | −0.11030 (9) | 0.2261 (2) | 0.0294 (5) | |
H1c2 | 0.329214 | −0.00477 | 0.204043 | 0.032* | |
H1c3 | 0.333185 | −0.138886 | 0.21059 | 0.0352* | |
H1n1 | 0.544 (5) | 0.108 (3) | 0.293 (7) | 0.033620 (2)* | 0.5 |
H2n1 | 0.559 (5) | 0.113 (3) | 0.242 (7) | 0.033620 (2)* | 0.5 |
H1n2 | 0.5 | −0.198938 | 0.25 | 0.0338* | |
H1o6w | 0.6228 (18) | 0.2806 (12) | 0.069 (4) | 0.016 (9)* | |
H2o6w | 0.642 (3) | 0.2512 (15) | 0.243 (5) | 0.000 (8)* | |
H1o5w1 | 0.605 (3) | 0.436 (2) | 0.094 (6) | −0.030 (6)* | 0.5 |
H2o5w1 | 0.629 (3) | 0.508 (3) | 0.239 (6) | −0.010 (8)* | 0.5 |
H1o5w2 | 0.631 (2) | 0.437 (2) | 0.123 (7) | −0.012 (7)* | 0.5 |
H2o5w2 | 0.630 (3) | 0.515 (3) | 0.239 (5) | −0.001 (8)* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01362 (15) | 0.01408 (15) | 0.01110 (16) | 0 | 0.00098 (12) | 0 |
S1 | 0.01275 (17) | 0.01712 (18) | 0.01179 (19) | 0.00005 (12) | 0.00129 (14) | 0.00043 (12) |
O2s | 0.0172 (5) | 0.0314 (6) | 0.0327 (7) | −0.0009 (4) | 0.0106 (5) | 0.0004 (5) |
O4s | 0.0431 (7) | 0.0153 (5) | 0.0270 (7) | −0.0005 (5) | 0.0128 (6) | 0.0016 (5) |
O3s | 0.0422 (12) | 0.0150 (9) | 0.0232 (15) | 0.0015 (8) | 0.0137 (10) | −0.0003 (10) |
O6w | 0.0359 (15) | 0.0348 (15) | 0.0279 (15) | 0.0201 (10) | 0.0147 (12) | 0.0082 (9) |
O5w1 | 0.094 (2) | 0.0295 (19) | 0.0460 (15) | −0.0328 (19) | 0.0502 (16) | −0.0181 (14) |
O5w2 | 0.0245 (19) | 0.0222 (14) | 0.0176 (18) | −0.0090 (12) | 0.0046 (13) | −0.0011 (11) |
N1 | 0.0214 (12) | 0.0180 (10) | 0.0435 (15) | 0 | 0.0032 (11) | 0 |
O1b1 | 0.0235 (9) | 0.019 (2) | 0.0152 (9) | 0.0029 (16) | −0.0046 (7) | −0.0039 (15) |
O1b2 | 0.019 (2) | 0.101 (6) | 0.0140 (15) | 0.001 (3) | −0.0031 (12) | 0.005 (2) |
N2 | 0.0348 (11) | 0.0140 (9) | 0.0336 (12) | 0 | 0.0009 (10) | 0 |
C1 | 0.0206 (10) | 0.0192 (10) | 0.0204 (11) | 0 | 0.0040 (9) | 0 |
C2 | 0.0171 (7) | 0.0241 (8) | 0.0379 (10) | 0.0008 (6) | 0.0026 (7) | −0.0008 (7) |
C3 | 0.0232 (8) | 0.0260 (8) | 0.0378 (10) | −0.0061 (7) | 0.0027 (7) | −0.0011 (7) |
Geometric parameters (Å, º) top | Average | Minimum | Maximum |
Fe1—O6w | 2.00 (2) | 1.94 (3) | 2.04 (3) |
Fe1—O6wi | 2.00 (2) | 1.93 (3) | 2.04 (3) |
Fe1—O5w1 | 2.01 (4) | 1.98 (6) | 2.02 (6) |
Fe1—O5w1i | 2.01 (4) | 1.98 (6) | 2.02 (6) |
Fe1—O5w2 | 2.033 (17) | 1.997 (18) | 2.074 (18) |
Fe1—O5w2i | 2.032 (17) | 1.996 (18) | 2.070 (18) |
Fe1—O1b1 | 1.946 (8) | 1.914 (8) | 2.001 (8) |
Fe1—O1b1i | 1.947 (8) | 1.914 (8) | 1.998 (8) |
Fe1—O1b2 | 1.917 (18) | 1.90 (3) | 1.93 (3) |
Fe1—O1b2i | 1.917 (18) | 1.90 (3) | 1.93 (3) |
Fe1—H1o5w1 | 2.33 (10) | 1.73 (10) | 2.68 (10) |
Fe1—H1o5w1i | 2.32 (10) | 1.76 (10) | 2.68 (10) |
S1—O2s | 1.4568 (18) | 1.4550 (18) | 1.4594 (18) |
S1—O4s | 1.468 (2) | 1.459 (2) | 1.481 (2) |
S1—O3s | 1.46 (2) | 1.45 (3) | 1.48 (3) |
S1—O1b1 | 1.506 (8) | 1.476 (8) | 1.582 (8) |
S1—O1b2 | 1.486 (18) | 1.48 (3) | 1.51 (3) |
S1—H2o5w1ii | 2.50 (12) | 1.36 (13) | 3.05 (13) |
S1—H2o5w2ii | 2.49 (13) | 1.07 (15) | 3.18 (15) |
O4s—H2o5w1ii | 1.46 (11) | 0.11 (13) | 2.10 (13) |
O4s—H2o5w2ii | 1.34 (13) | 0.11 (15) | 1.97 (15) |
O6w—H1o6w | 0.84 (13) | 0.43 (16) | 1.25 (16) |
O6w—H2o6w | 0.72 (8) | 0.13 (10) | 1.41 (10) |
O5w1—H1o5w1 | 0.73 (11) | 0.37 (12) | 1.07 (12) |
O5w1—H2o5w1 | 1.35 (12) | 0.59 (13) | 3.56 (13) |
O5w2—H1o5w1 | 0.59 (10) | 0.53 (10) | 0.65 (10) |
O5w2—H1o5w2 | 0.83 (11) | 0.46 (12) | 1.20 (12) |
O5w2—H2o5w2 | 1.40 (13) | 0.66 (15) | 3.36 (15) |
N1—C1 | 1.331 (3) | 1.330 (4) | 1.332 (4) |
N1—H1n1 | 0.66 (6) | 0.65 (6) | 0.66 (6) |
N1—H1n1i | 0.66 (6) | 0.65 (6) | 0.66 (6) |
N1—H2n1 | 0.85 (6) | 0.85 (6) | 0.85 (6) |
N1—H2n1i | 0.85 (6) | 0.85 (6) | 0.85 (6) |
N2—C3 | 1.345 (3) | 1.344 (3) | 1.346 (3) |
N2—C3i | 1.345 (3) | 1.344 (3) | 1.346 (3) |
N2—H1n2 | 0.9 (17) | 0.9 (17) | 0.9 (17) |
C1—C2 | 1.406 (3) | 1.404 (3) | 1.408 (3) |
C1—C2i | 1.406 (3) | 1.404 (3) | 1.408 (3) |
C2—C3 | 1.360 (3) | 1.358 (3) | 1.361 (3) |
C2—H1c2 | 1.0 (13) | 1.0 (13) | 1.0 (13) |
C3—H1c3 | 1.0 (14) | 1.0 (14) | 1.0 (14) |
H1n1—H2n1 | 0.43 (8) | 0.43 (8) | 0.44 (8) |
H1o5w1—H2o5w1 | 1.68 (15) | 0.89 (16) | 3.41 (16) |
H1o5w2—H2o5w2 | 1.52 (16) | 0.93 (18) | 2.20 (18) |
| | | |
O6w—Fe1—O6wi | 91.9 (10) | 88.6 (9) | 94.4 (9) |
O6w—Fe1—O5w1 | 88.9 (9) | 85.9 (8) | 91.1 (9) |
O6w—Fe1—O5w1i | 175.9 (8) | 171.5 (7) | 178.9 (9) |
O6w—Fe1—O5w2 | 88.9 (9) | 87.4 (8) | 96.0 (8) |
O6w—Fe1—O5w2i | 176.2 (8) | 168.0 (7) | 178.3 (8) |
O6w—Fe1—O1b1 | 86.8 (7) | 81.4 (6) | 100.2 (6) |
O6w—Fe1—O1b1i | 90.9 (7) | 83.2 (6) | 101.5 (6) |
O6w—Fe1—O1b2 | 88.4 (7) | 82.3 (6) | 97.0 (6) |
O6w—Fe1—O1b2i | 92.1 (7) | 88.3 (6) | 98.1 (6) |
O6w—Fe1—H1o5w1 | 83 (2) | 76 (2) | 108 (3) |
O6w—Fe1—H1o5w1i | 164 (2) | 156 (2) | 172 (2) |
O6wi—Fe1—O5w1 | 175.9 (8) | 171.6 (7) | 178.9 (9) |
O6wi—Fe1—O5w1i | 88.8 (9) | 85.9 (8) | 91.1 (9) |
O6wi—Fe1—O5w2 | 176.1 (8) | 167.6 (7) | 178.4 (9) |
O6wi—Fe1—O5w2i | 88.9 (9) | 87.4 (9) | 95.7 (8) |
O6wi—Fe1—O1b1 | 90.9 (7) | 83.4 (6) | 101.6 (6) |
O6wi—Fe1—O1b1i | 86.8 (7) | 81.4 (6) | 100.0 (6) |
O6wi—Fe1—O1b2 | 92.1 (7) | 88.3 (7) | 98.1 (6) |
O6wi—Fe1—O1b2i | 88.4 (7) | 82.3 (6) | 97.0 (6) |
O6wi—Fe1—H1o5w1 | 164 (2) | 156 (2) | 172 (2) |
O6wi—Fe1—H1o5w1i | 83 (2) | 76 (2) | 105 (3) |
O5w1—Fe1—O5w1i | 88.6 (10) | 88.1 (8) | 89.7 (14) |
O5w1—Fe1—O5w2i | 93.5 (16) | 91.7 (12) | 94.5 (15) |
O5w1—Fe1—O1b1 | 86.1 (10) | 73.0 (13) | 91.4 (13) |
O5w1—Fe1—O1b1i | 95.3 (8) | 85.6 (9) | 104.1 (13) |
O5w1—Fe1—O1b2i | 92.9 (13) | 86.5 (10) | 101.0 (13) |
O5w1—Fe1—H1o5w1 | 16 (2) | 10 (2) | 21 (3) |
O5w1i—Fe1—O5w2 | 93.6 (16) | 91.8 (12) | 94.5 (15) |
O5w1i—Fe1—O1b1 | 95.3 (8) | 85.4 (9) | 104.0 (13) |
O5w1i—Fe1—O1b1i | 86.1 (10) | 73.1 (13) | 91.4 (13) |
O5w1i—Fe1—O1b2 | 93.1 (13) | 86.6 (10) | 101.2 (13) |
O5w1i—Fe1—H1o5w1i | 16 (2) | 10 (2) | 21 (2) |
O5w2—Fe1—O5w2i | 88.3 (7) | 84.6 (7) | 90.4 (7) |
O5w2—Fe1—O1b1i | 97.2 (5) | 96.4 (5) | 99.1 (5) |
O5w2—Fe1—O1b2 | 85.0 (5) | 71.7 (5) | 89.6 (5) |
O5w2—Fe1—O1b2i | 95.4 (5) | 85.6 (5) | 107.0 (5) |
O5w2—Fe1—H1o5w1i | 92 (2) | 75 (3) | 102.2 (19) |
O5w2i—Fe1—O1b1 | 97.2 (5) | 96.5 (5) | 98.9 (5) |
O5w2i—Fe1—O1b2 | 95.1 (5) | 85.6 (5) | 106.8 (5) |
O5w2i—Fe1—O1b2i | 85.1 (5) | 72.0 (5) | 89.6 (5) |
O5w2i—Fe1—H1o5w1 | 92 (2) | 73 (3) | 102.4 (19) |
O1b1—Fe1—O1b1i | 177.0 (4) | 175.2 (4) | 178.1 (4) |
O1b1—Fe1—O1b2i | 172.0 (5) | 164.7 (5) | 175.7 (4) |
O1b1—Fe1—H1o5w1 | 78 (2) | 72.3 (19) | 95 (3) |
O1b1i—Fe1—O1b2 | 171.8 (5) | 164.3 (5) | 175.7 (4) |
O1b1i—Fe1—H1o5w1i | 78 (2) | 72.3 (19) | 93 (3) |
O1b2—Fe1—O1b2i | 175.9 (9) | 174.6 (11) | 177.7 (11) |
O1b2—Fe1—H1o5w1i | 103 (2) | 99 (3) | 104 (2) |
O1b2i—Fe1—H1o5w1 | 103 (3) | 98 (3) | 104 (2) |
O2s—S1—O4s | 111.36 (12) | 111.02 (12) | 111.62 (12) |
O2s—S1—O3s | 110.5 (9) | 107.3 (9) | 112.6 (9) |
O2s—S1—O1b1 | 109.6 (4) | 107.1 (4) | 110.6 (3) |
O2s—S1—O1b2 | 108.9 (4) | 105.2 (4) | 111.6 (4) |
O2s—S1—H2o5w1ii | 110 (3) | 101 (4) | 113 (2) |
O2s—S1—H2o5w2ii | 108 (2) | 104.9 (18) | 114 (4) |
O4s—S1—O3s | 110.1 (9) | 102.6 (8) | 117.5 (8) |
O4s—S1—O1b1 | 108.0 (4) | 95.7 (4) | 117.8 (4) |
O4s—S1—O1b2 | 105.7 (5) | 95.8 (5) | 111.3 (5) |
O4s—S1—H2o5w1ii | 29 (2) | 3(4) | 39.2 (16) |
O4s—S1—H2o5w2ii | 22 (2) | 3(4) | 39 (6) |
O3s—S1—O1b1 | 107.5 (9) | 100.9 (8) | 124.9 (11) |
O3s—S1—O1b2 | 109.1 (9) | 100.4 (9) | 123.0 (11) |
O3s—S1—H2o5w1ii | 127 (3) | 86 (5) | 141 (2) |
O3s—S1—H2o5w2ii | 125 (3) | 70 (6) | 135 (2) |
O1b1—S1—H2o5w2ii | 97 (2) | 92.0 (16) | 131 (5) |
O1b2—S1—H2o5w1ii | 85 (2) | 69.4 (19) | 132 (4) |
H2o5w1ii—S1—H2o5w2ii | 58 (6) | 48 (6) | 67 (6) |
S1—O4s—H2o5w1ii | 115 (7) | 67 (7) | 140 (30) |
S1—O4s—H2o5w2ii | 118 (7) | 30 (30) | 135 (3) |
H2o5w1ii—O4s—H2o5w2ii | 173 (7) | 173 (6) | 174 (7) |
Fe1—O6w—H1o6w | 117 (13) | 108 (17) | 130 (20) |
Fe1—O6w—H2o6w | 130 (12) | 125 (5) | 140 (40) |
H1o6w—O6w—H2o6w | 107 (17) | 80 (11) | 120 (11) |
Fe1—O5w1—H1o5w1 | 106 (8) | 59 (7) | 118 (6) |
Fe1—O5w1—H2o5w1 | 129 (7) | 124 (6) | 133 (5) |
H1o5w1—O5w1—H2o5w1 | 105 (12) | 63 (11) | 114 (12) |
Fe1—O5w2—H1o5w1 | 69 (8) | 68 (7) | 70 (9) |
Fe1—O5w2—H1o5w2 | 118 (7) | 81 (4) | 178 (13) |
Fe1—O5w2—H2o5w2 | 129 (5) | 124 (6) | 134 (8) |
H1o5w2—O5w2—H2o5w2 | 88 (9) | 37 (9) | 113 (10) |
C1—N1—H1n1 | 122 (5) | 122 (5) | 123 (5) |
C1—N1—H1n1i | 122 (5) | 122 (5) | 123 (5) |
C1—N1—H2n1 | 121 (4) | 120 (4) | 121 (4) |
C1—N1—H2n1i | 121 (4) | 120 (4) | 121 (4) |
H1n1—N1—H1n1i | 116 (7) | 115 (7) | 117 (7) |
H1n1—N1—H2n1 | 30 (6) | 30 (5) | 30 (6) |
H1n1—N1—H2n1i | 109 (6) | 108 (6) | 110 (6) |
H1n1i—N1—H2n1 | 109 (6) | 108 (6) | 110 (6) |
H1n1i—N1—H2n1i | 30 (6) | 30 (5) | 30 (6) |
H2n1—N1—H2n1i | 119 (5) | 118 (5) | 119 (5) |
Fe1—O1b1—S1 | 148.2 (6) | 134.8 (6) | 155.9 (6) |
Fe1—O1b2—S1 | 153.5 (15) | 150 (2) | 158 (2) |
C3—N2—C3i | 121.3 (2) | 121.3 (2) | 121.3 (2) |
C3—N2—H1n2 | 119.34 | 119.33 | 119.35 |
C3i—N2—H1n2 | 119.34 | 119.33 | 119.35 |
N1—C1—C2 | 121.37 (17) | 121.32 (14) | 121.42 (14) |
N1—C1—C2i | 121.37 (17) | 121.32 (14) | 121.42 (14) |
C2—C1—C2i | 117.3 (2) | 117.2 (3) | 117.3 (3) |
C1—C2—C3 | 120.2 (2) | 120.1 (2) | 120.3 (2) |
C1—C2—H1c2 | 119.9 | 119.85 | 119.94 |
C3—C2—H1c2 | 119.9 | 119.85 | 119.94 |
N2—C3—C2 | 120.5 (2) | 120.5 (2) | 120.5 (2) |
N2—C3—H1c3 | 119.75 | 119.73 | 119.77 |
C2—C3—H1c3 | 119.75 | 119.73 | 119.77 |
N1—H1n1—H2n1 | 101 (10) | 100 (10) | 101 (10) |
N1—H2n1—H1n1 | 49 (9) | 49 (9) | 50 (9) |
Fe1—H1o5w1—O5w1 | 58 (8) | 42 (4) | 101 (11) |
Fe1—H1o5w1—O5w2 | 93 (10) | 92 (9) | 94 (11) |
Fe1—H1o5w1—H2o5w1 | 96 (6) | 68 (6) | 148 (9) |
O5w1—H1o5w1—H2o5w1 | 47 (9) | 25 (5) | 84 (13) |
S1ii—H2o5w1—O4sii | 36 (7) | 24 (2) | 90 (17) |
S1ii—H2o5w1—O5w1 | 144 (8) | 91 (5) | 159 (10) |
S1ii—H2o5w1—H1o5w1 | 126 (7) | 98 (5) | 168 (9) |
O4sii—H2o5w1—O5w1 | 151 (14) | 16 (6) | 179 (14) |
O4sii—H2o5w1—H1o5w1 | 136 (12) | 14 (8) | 170 (11) |
O5w1—H2o5w1—H1o5w1 | 28 (6) | 8(2) | 43 (8) |
O5w2—H1o5w2—H2o5w2 | 59 (8) | 27 (5) | 132 (11) |
S1ii—H2o5w2—O4sii | 41 (8) | 19.0 (15) | 150 (60) |
S1ii—H2o5w2—O5w2 | 151 (8) | 101 (7) | 162 (10) |
S1ii—H2o5w2—H1o5w2 | 131 (8) | 119 (7) | 156 (9) |
O4sii—H2o5w2—O5w2 | 150 (14) | 10 (7) | 180 (11) |
O4sii—H2o5w2—H1o5w2 | 142 (13) | 30 (50) | 159 (16) |
O5w2—H2o5w2—H1o5w2 | 33 (5) | 10 (2) | 53 (8) |
Symmetry codes: (i) −x1+1, x2, −x3+1/2, −x4+1/2; (ii) −x1+1, −x2+1, −x3, −x4. |
Crystal data top
C5N2O12S2FeH15 | Z = 4 |
Mr = 415.1 | F(000) = 852 |
Monoclinic, X2/c(α0γ)0s† | Dx = 1.979 Mg m−3 |
q = 0.336600a* + 0.554400c* | Mo Kα radiation, λ = 0.71073 Å |
a = 12.175 (11) Å | Cell parameters from 7559 reflections |
b = 17.217 (5) Å | θ = 3.4–29.3° |
c = 6.769 (2) Å | µ = 1.45 mm−1 |
β = 100.87 (4)° | T = 195 K |
V = 1393.4 (14) Å3 | 0.51 × 0.44 × 0.30 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, x2, −x3+1/2, −x4+1/2; (3) −x1, −x2, −x3, −x4; (4) x1, −x2, x3+1/2, x4+1/2; (5) x1+1/2, x2+1/2, x3, x4+1/2; (6) −x1+1/2, x2+1/2, −x3+1/2, −x4; (7) −x1+1/2, −x2+1/2, −x3, −x4+1/2; (8) x1+1/2, −x2+1/2, x3+1/2, x4.
|
Data collection top
Xcalibur, Atlas diffractometer | 5282 independent reflections |
Radiation source: X-ray tube | 3721 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 10.6249 pixels mm-1 | θmax = 29.6°, θmin = 2.4° |
ω scans | h = −17→16 |
Absorption correction: gaussian Jana2006 | k = −23→22 |
Tmin = 0.583, Tmax = 0.752 | l = −9→9 |
23241 measured reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
wR(F2) = 0.075 | (Δ/σ)max = 0.047 |
S = 2.01 | Δρmax = 0.76 e Å−3 |
5282 reflections | Δρmin = −0.45 e Å−3 |
343 parameters | Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
7 restraints | Extinction coefficient: 5320 (160) |
105 constraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 1 | 0.643241 (12) | 0.25 | 0.01092 (8) | |
S1 | 0.83288 (2) | 0.649134 (15) | −0.19644 (4) | 0.01169 (9) | |
O1b1 | 0.92703 (17) | 0.66428 (13) | −0.0272 (3) | 0.0292 (5) | 0.5 |
O1b2 | 0.92889 (17) | 0.62694 (10) | −0.0238 (3) | 0.0236 (4) | 0.5 |
O2s | 0.72909 (7) | 0.65734 (5) | −0.11977 (13) | 0.0213 (3) | |
O3s | 0.85049 (7) | 0.71561 (5) | −0.31897 (12) | 0.0227 (3) | |
O5w1 | 1.08154 (17) | 0.55665 (9) | 0.1413 (2) | 0.0317 (5) | 0.5 |
O5w2 | 1.11916 (17) | 0.56749 (8) | 0.1928 (2) | 0.0214 (4) | 0.5 |
O6w | 1.10435 (9) | 0.72361 (6) | 0.17929 (15) | 0.0239 (3) | |
O4s | 0.83380 (9) | 0.57748 (5) | −0.31196 (16) | 0.0209 (6) | |
N1 | 0.5 | 0.41157 (8) | 0.25 | 0.0222 (5) | |
N2 | 0.5 | 0.64870 (8) | 0.25 | 0.0229 (5) | |
C1 | 0.5 | 0.48873 (9) | 0.25 | 0.0170 (5) | |
C2 | 0.39927 (10) | 0.53146 (7) | 0.22442 (19) | 0.0222 (4) | |
C3 | 0.40184 (10) | 0.61031 (7) | 0.22710 (19) | 0.0245 (4) | |
H1c2 | 0.328874 | 0.504717 | 0.205097 | 0.0266* | |
H1c3 | 0.333164 | 0.638985 | 0.212572 | 0.0294* | |
H1n1 | 0.5581 (16) | 0.3871 (16) | 0.224 (4) | 0.0267 (4)* | 0.5 |
H2n1 | 0.4409 (15) | 0.3878 (16) | 0.186 (4) | 0.0267 (4)* | 0.5 |
H1n2 | 0.5 | 0.699228 | 0.25 | 0.0275* | |
H1o6w | 1.1217 (12) | 0.7187 (8) | 0.0715 (13) | 0.0287 (13)* | |
H1o5w1 | 1.1032 (17) | 0.5621 (11) | 0.0374 (18) | 0.038033 (2)* | 0.5 |
H2o5w1 | 1.1076 (15) | 0.5181 (7) | 0.198 (3) | 0.038033 (2)* | 0.5 |
H2o6w | 1.1446 (10) | 0.7517 (7) | 0.2552 (16) | 0.0287 (16)* | |
H1o5w2 | 1.1302 (16) | 0.5700 (10) | 0.0799 (14) | 0.0256 (14)* | 0.5 |
H2o5w2 | 1.1252 (15) | 0.5231 (5) | 0.228 (3) | 0.0256 (3)* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01136 (12) | 0.01141 (13) | 0.00961 (14) | 0 | 0.00097 (9) | 0 |
S1 | 0.01085 (14) | 0.01380 (15) | 0.01008 (16) | −0.00005 (10) | 0.00111 (11) | −0.00030 (10) |
O1b1 | 0.0172 (7) | 0.0541 (9) | 0.0137 (7) | −0.0033 (8) | −0.0038 (5) | 0.0035 (8) |
O1b2 | 0.0168 (6) | 0.0384 (8) | 0.0130 (7) | 0.0050 (7) | −0.0036 (5) | −0.0052 (7) |
O2s | 0.0145 (4) | 0.0261 (5) | 0.0250 (5) | 0.0003 (3) | 0.0079 (4) | −0.0006 (4) |
O3s | 0.0343 (5) | 0.0140 (4) | 0.0222 (5) | −0.0001 (4) | 0.0118 (4) | 0.0018 (3) |
O5w1 | 0.0564 (11) | 0.0190 (7) | 0.0272 (8) | 0.0183 (7) | 0.0270 (8) | 0.0088 (6) |
O5w2 | 0.0288 (8) | 0.0179 (7) | 0.0201 (7) | 0.0101 (6) | 0.0113 (6) | 0.0058 (5) |
O6w | 0.0289 (5) | 0.0275 (5) | 0.0174 (5) | −0.0162 (4) | 0.0099 (4) | −0.0063 (4) |
O4s | 0.0318 (11) | 0.0132 (7) | 0.0190 (12) | 0.0003 (7) | 0.0080 (8) | −0.0010 (7) |
N1 | 0.0172 (7) | 0.0149 (7) | 0.0334 (9) | 0 | 0.0018 (7) | 0 |
N2 | 0.0279 (8) | 0.0120 (7) | 0.0272 (9) | 0 | 0.0009 (7) | 0 |
C1 | 0.0172 (8) | 0.0168 (8) | 0.0167 (8) | 0 | 0.0028 (7) | 0 |
C2 | 0.0144 (5) | 0.0201 (6) | 0.0311 (7) | −0.0006 (5) | 0.0023 (5) | −0.0001 (5) |
C3 | 0.0201 (6) | 0.0218 (6) | 0.0304 (7) | 0.0049 (5) | 0.0020 (6) | 0.0007 (5) |
Geometric parameters (Å, º) top | Average | Minimum | Maximum |
Fe1—O1b1 | 1.937 (6) | 1.926 (9) | 1.950 (9) |
Fe1—O1b1i | 1.937 (6) | 1.926 (9) | 1.950 (9) |
Fe1—O1b2 | 1.929 (6) | 1.904 (9) | 1.937 (9) |
Fe1—O1b2i | 1.929 (6) | 1.904 (9) | 1.937 (9) |
Fe1—O5w1 | 2.012 (7) | 2.002 (10) | 2.028 (10) |
Fe1—O5w1i | 2.012 (7) | 2.002 (10) | 2.028 (10) |
Fe1—O5w2 | 2.032 (7) | 2.023 (11) | 2.058 (11) |
Fe1—O5w2i | 2.031 (7) | 2.023 (11) | 2.058 (11) |
Fe1—O6w | 2.007 (6) | 1.979 (8) | 2.036 (8) |
Fe1—O6wi | 2.007 (6) | 1.978 (8) | 2.036 (8) |
S1—O1b1 | 1.493 (6) | 1.476 (9) | 1.514 (9) |
S1—O1b2 | 1.503 (6) | 1.483 (8) | 1.551 (8) |
S1—O2s | 1.462 (3) | 1.460 (3) | 1.465 (3) |
S1—O3s | 1.4612 (14) | 1.4518 (14) | 1.4746 (14) |
S1—O4s | 1.47 (2) | 1.47 (3) | 1.48 (3) |
O5w1—H1o5w1 | 0.801 (18) | 0.80 (2) | 0.80 (2) |
O5w1—H2o5w1 | 0.801 (16) | 0.801 (18) | 0.801 (18) |
O5w2—H1o5w2 | 0.801 (14) | 0.801 (16) | 0.801 (16) |
O5w2—H2o5w2 | 0.801 (11) | 0.801 (12) | 0.801 (12) |
O6w—H1o6w | 0.801 (12) | 0.801 (12) | 0.801 (12) |
O6w—H2o6w | 0.801 (13) | 0.801 (13) | 0.801 (13) |
N1—C1 | 1.328 (3) | 1.322 (3) | 1.335 (3) |
N1—H1n1 | 0.87 (2) | 0.87 (2) | 0.87 (2) |
N1—H1n1ii | 0.87 (2) | 0.87 (2) | 0.87 (2) |
N1—H2n1 | 0.87 (2) | 0.86 (2) | 0.88 (2) |
N1—H2n1ii | 0.87 (2) | 0.86 (2) | 0.88 (2) |
N2—C3 | 1.349 (3) | 1.348 (3) | 1.350 (3) |
N2—C3ii | 1.349 (3) | 1.348 (3) | 1.350 (3) |
N2—H1n2 | 0.9 (17) | 0.9 (17) | 0.9 (17) |
C1—C2 | 1.413 (3) | 1.410 (4) | 1.416 (4) |
C1—C2ii | 1.413 (3) | 1.410 (4) | 1.416 (4) |
C2—C3 | 1.358 (3) | 1.358 (3) | 1.358 (3) |
C2—H1c2 | 1.0 (13) | 1.0 (13) | 1.0 (13) |
C3—H1c3 | 1.0 (14) | 1.0 (14) | 1.0 (14) |
H1n1—H2n1ii | 0.61 (4) | 0.60 (4) | 0.61 (4) |
| | | |
O1b1—Fe1—O1b2i | 177.5 (2) | 174.9 (3) | 178.6 (3) |
O1b1—Fe1—O5w1 | 87.5 (2) | 87.09 (18) | 88.6 (3) |
O1b1—Fe1—O5w2i | 96.0 (2) | 93.7 (3) | 96.6 (2) |
O1b1—Fe1—O6w | 85.1 (2) | 80.2 (3) | 86.82 (14) |
O1b1—Fe1—O6wi | 89.0 (2) | 85.1 (3) | 90.35 (13) |
O1b1i—Fe1—O1b2 | 177.5 (2) | 174.9 (3) | 178.6 (3) |
O1b1i—Fe1—O5w1i | 87.5 (2) | 87.09 (18) | 88.6 (3) |
O1b1i—Fe1—O5w2 | 96.0 (2) | 93.7 (3) | 96.6 (2) |
O1b1i—Fe1—O6w | 89.0 (2) | 85.1 (3) | 90.35 (13) |
O1b1i—Fe1—O6wi | 85.1 (2) | 80.2 (3) | 86.82 (14) |
O1b2—Fe1—O5w1i | 94.01 (19) | 92.6 (2) | 95.3 (2) |
O1b2—Fe1—O5w2 | 85.87 (19) | 85.01 (15) | 88.1 (2) |
O1b2—Fe1—O6w | 89.6 (2) | 88.7 (3) | 91.4 (2) |
O1b2—Fe1—O6wi | 93.0 (2) | 91.7 (2) | 96.3 (2) |
O1b2i—Fe1—O5w1 | 94.00 (19) | 92.6 (2) | 95.3 (2) |
O1b2i—Fe1—O5w2i | 85.85 (19) | 85.01 (15) | 88.1 (2) |
O1b2i—Fe1—O6w | 92.9 (2) | 91.7 (2) | 96.3 (2) |
O1b2i—Fe1—O6wi | 89.5 (2) | 88.7 (3) | 91.4 (2) |
O5w1—Fe1—O5w2i | 90.9 (2) | 89.83 (13) | 92.49 (13) |
O5w1—Fe1—O6w | 90.4 (3) | 89.1 (3) | 93.18 (18) |
O5w1—Fe1—O6wi | 175.6 (2) | 171.29 (15) | 177.4 (2) |
O5w1i—Fe1—O5w2 | 90.9 (2) | 89.83 (13) | 92.48 (13) |
O5w1i—Fe1—O6w | 175.5 (2) | 171.30 (15) | 177.4 (2) |
O5w1i—Fe1—O6wi | 90.4 (3) | 89.1 (3) | 93.19 (18) |
O5w2—Fe1—O6w | 86.8 (2) | 82.13 (18) | 88.7 (3) |
O5w2—Fe1—O6wi | 177.10 (19) | 173.04 (16) | 178.60 (18) |
O5w2i—Fe1—O6w | 177.09 (19) | 173.01 (16) | 178.60 (18) |
O5w2i—Fe1—O6wi | 86.9 (2) | 82.11 (18) | 88.7 (3) |
O6w—Fe1—O6wi | 91.8 (2) | 91.6 (2) | 92.4 (3) |
O1b1—S1—O2s | 109.0 (3) | 108.0 (3) | 109.4 (4) |
O1b1—S1—O3s | 105.0 (3) | 96.9 (3) | 109.76 (19) |
O1b1—S1—O4s | 110.2 (9) | 104.9 (8) | 119.1 (9) |
O1b2—S1—O2s | 109.4 (3) | 108.47 (18) | 110.6 (3) |
O1b2—S1—O3s | 110.1 (2) | 107.13 (15) | 117.6 (3) |
O1b2—S1—O4s | 104.8 (9) | 100.8 (9) | 106.3 (9) |
O2s—S1—O3s | 110.62 (8) | 110.08 (8) | 111.03 (8) |
O2s—S1—O4s | 111.3 (9) | 109.7 (9) | 112.0 (9) |
O3s—S1—O4s | 110.4 (10) | 106.2 (10) | 112.2 (10) |
Fe1—O1b1—S1 | 150.3 (4) | 145.7 (6) | 152.5 (3) |
Fe1—O1b2—S1 | 148.9 (4) | 143.7 (5) | 150.8 (2) |
Fe1—O5w1—H1o5w1 | 120.0 (15) | 117.9 (14) | 120.9 (16) |
Fe1—O5w1—H2o5w1 | 128.4 (15) | 127.6 (16) | 130.1 (13) |
H1o5w1—O5w1—H2o5w1 | 111 (2) | 111 (2) | 111 (2) |
Fe1—O5w2—H1o5w2 | 113.9 (14) | 113.0 (13) | 114.2 (15) |
Fe1—O5w2—H2o5w2 | 125.6 (16) | 124.3 (14) | 126.2 (18) |
H1o5w2—O5w2—H2o5w2 | 108.4 (19) | 108.4 (19) | 108.4 (19) |
Fe1—O6w—H1o6w | 115.5 (12) | 113.0 (12) | 118.3 (12) |
Fe1—O6w—H2o6w | 127.1 (10) | 121.9 (9) | 131.5 (10) |
H1o6w—O6w—H2o6w | 114.4 (15) | 114.4 (16) | 114.4 (16) |
C1—N1—H1n1 | 119.0 (17) | 118.7 (17) | 119.3 (17) |
C1—N1—H1n1ii | 119.0 (17) | 118.7 (17) | 119.3 (17) |
C1—N1—H2n1 | 118.1 (17) | 117.3 (17) | 118.9 (17) |
C1—N1—H2n1ii | 118.1 (17) | 117.3 (17) | 118.9 (17) |
H1n1—N1—H1n1ii | 122 (2) | 122 (2) | 122 (2) |
H1n1—N1—H2n1 | 107 (2) | 107 (2) | 108 (2) |
H1n1—N1—H2n1ii | 41 (2) | 40 (2) | 41 (2) |
H1n1ii—N1—H2n1 | 41 (2) | 40 (2) | 41 (2) |
H1n1ii—N1—H2n1ii | 107 (2) | 107 (2) | 108 (2) |
H2n1—N1—H2n1ii | 124 (2) | 123 (2) | 125 (2) |
C3—N2—C3ii | 121.31 (17) | 121.2 (2) | 121.4 (2) |
C3—N2—H1n2 | 119.34 | 119.31 | 119.38 |
C3ii—N2—H1n2 | 119.34 | 119.31 | 119.38 |
N1—C1—C2 | 121.39 (13) | 120.66 (16) | 122.13 (16) |
N1—C1—C2ii | 121.39 (13) | 120.66 (16) | 122.13 (16) |
C2—C1—C2ii | 117.22 (18) | 117.1 (2) | 117.3 (2) |
C1—C2—C3 | 120.12 (17) | 120.03 (17) | 120.22 (17) |
C1—C2—H1c2 | 119.94 | 119.89 | 119.98 |
C3—C2—H1c2 | 119.94 | 119.89 | 119.99 |
N2—C3—C2 | 120.60 (18) | 120.56 (17) | 120.65 (17) |
N2—C3—H1c3 | 119.7 | 119.68 | 119.72 |
C2—C3—H1c3 | 119.7 | 119.67 | 119.72 |
N1—H1n1—H2n1ii | 70 (3) | 69 (3) | 70 (3) |
N1—H2n1—H1n1ii | 70 (3) | 69 (3) | 70 (3) |
Symmetry codes: (i) −x1+2, x2, −x3+1/2, −x4+1/2; (ii) −x1+1, x2, −x3+1/2, −x4+1/2. |
Crystal data top
C5H15FeN2O12S2 | Z = 4 |
Mr = 415.16 | F(000) = 852 |
Triclinic, P1 | Dx = 1.997 Mg m−3 |
a = 10.516 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.873 (4) Å | Cell parameters from 2322 reflections |
c = 13.099 (4) Å | θ = 2.4–29.3° |
α = 65.34 (3)° | µ = 1.46 mm−1 |
β = 77.51 (3)° | T = 80 K |
γ = 68.73 (3)° | Block, yellow |
V = 1381.0 (9) Å3 | 0.47 × 0.40 × 0.27 mm |
Data collection top
Xcalibur, Atlas diffractometer | 5963 reflections with I > 2σ(I) |
Detector resolution: 10.6249 pixels mm-1 | Rint = 0.018 |
ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: analytical CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −12→12 |
Tmin = 0.592, Tmax = 0.764 | k = −14→14 |
7895 measured reflections | l = −16→16 |
7895 independent reflections | |
Refinement top
Refinement on F2 | 28 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
7895 reflections | Δρmax = 0.36 e Å−3 |
446 parameters | Δρmin = −0.60 e Å−3 |
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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.85489 (5) | 0.80465 (5) | 0.05110 (4) | 0.00606 (9) | |
O11W | 0.8995 (2) | 0.7303 (2) | −0.06833 (19) | 0.0149 (5) | |
H11A | 0.895 (3) | 0.659 (2) | −0.062 (2) | 0.022* | |
H11B | 0.917 (3) | 0.785 (2) | −0.1299 (18) | 0.022* | |
O12W | 1.0244 (2) | 0.8607 (2) | −0.00306 (17) | 0.0180 (5) | |
H12A | 1.090 (2) | 0.848 (2) | 0.032 (2) | 0.027* | |
H12B | 1.035 (3) | 0.899 (2) | −0.0698 (16) | 0.027* | |
O13W | 0.81186 (18) | 0.87453 (18) | 0.17633 (15) | 0.0121 (4) | |
H13A | 0.797 (2) | 0.821 (2) | 0.2440 (16) | 0.018* | |
H13B | 0.855 (3) | 0.909 (2) | 0.196 (2) | 0.018* | |
O14W | 0.6785 (2) | 0.7595 (2) | 0.10258 (19) | 0.0129 (5) | |
H14A | 0.600 (2) | 0.812 (2) | 0.078 (2) | 0.019* | |
H14B | 0.659 (3) | 0.716 (2) | 0.1693 (16) | 0.019* | |
S11 | 1.02552 (8) | 0.49807 (7) | 0.19250 (6) | 0.00594 (17) | |
O11 | 0.94714 (15) | 0.63949 (14) | 0.16268 (12) | 0.0119 (3) | |
O12 | 1.1177 (2) | 0.4786 (2) | 0.09617 (18) | 0.0117 (5) | |
O13 | 1.1034 (2) | 0.4622 (2) | 0.28774 (19) | 0.0105 (5) | |
O14 | 0.9275 (2) | 0.4234 (2) | 0.2238 (2) | 0.0120 (5) | |
S12 | 0.67609 (8) | 1.10656 (8) | −0.09414 (6) | 0.00639 (18) | |
O15 | 0.75980 (15) | 0.96622 (14) | −0.06330 (12) | 0.0140 (3) | |
O16 | 0.7677 (2) | 1.1834 (2) | −0.10813 (19) | 0.0129 (5) | |
O17 | 0.6192 (2) | 1.14596 (19) | −0.19994 (18) | 0.0115 (5) | |
O18 | 0.5663 (2) | 1.1188 (2) | −0.00516 (19) | 0.0106 (5) | |
Fe2 | 0.14147 (5) | 0.69703 (5) | 0.44620 (4) | 0.00613 (9) | |
O21W | 0.12655 (18) | 0.67397 (18) | 0.30560 (15) | 0.0138 (4) | |
H21A | 0.160 (2) | 0.717 (2) | 0.2402 (16) | 0.021* | |
H21B | 0.126 (3) | 0.607 (2) | 0.299 (2) | 0.021* | |
O22W | 0.3376 (2) | 0.69092 (19) | 0.39982 (19) | 0.0136 (5) | |
H22A | 0.406 (2) | 0.656 (2) | 0.433 (2) | 0.020* | |
H22B | 0.359 (3) | 0.750 (2) | 0.3361 (18) | 0.020* | |
O23W | 0.1403 (2) | 0.73612 (19) | 0.58166 (18) | 0.0106 (5) | |
H23A | 0.129 (3) | 0.8129 (19) | 0.576 (2) | 0.016* | |
H23B | 0.106 (3) | 0.690 (2) | 0.6342 (18) | 0.016* | |
O24W | −0.05504 (19) | 0.69447 (17) | 0.49652 (16) | 0.0105 (4) | |
H24A | −0.062 (3) | 0.645 (2) | 0.5571 (17) | 0.016* | |
H24B | −0.108 (2) | 0.697 (2) | 0.4532 (19) | 0.016* | |
S21 | 0.30787 (8) | 0.39157 (8) | 0.58710 (7) | 0.00705 (17) | |
O21 | 0.19184 (14) | 0.51098 (14) | 0.53521 (12) | 0.0121 (3) | |
O22 | 0.4257 (2) | 0.3861 (2) | 0.50322 (18) | 0.0105 (5) | |
O23 | 0.34297 (19) | 0.39600 (19) | 0.68592 (18) | 0.0114 (5) | |
O24 | 0.2543 (2) | 0.2805 (2) | 0.61826 (19) | 0.0101 (5) | |
S22 | −0.01189 (8) | 1.01117 (7) | 0.31362 (6) | 0.00706 (19) | |
O25 | 0.09707 (15) | 0.88340 (14) | 0.35703 (13) | 0.0125 (3) | |
O26 | 0.0580 (2) | 1.11249 (19) | 0.27131 (19) | 0.0102 (5) | |
O27 | −0.0733 (2) | 1.0135 (2) | 0.22243 (18) | 0.0126 (5) | |
O28 | −0.1149 (2) | 1.0298 (2) | 0.40460 (19) | 0.0125 (6) | |
N11 | 0.6558 (3) | 0.4454 (3) | 0.1977 (3) | 0.0104 (4) | |
H11 | 0.7086 | 0.4706 | 0.2218 | 0.013* | |
C12 | 0.7124 (4) | 0.3670 (4) | 0.1404 (3) | 0.0134 (9) | |
H12 | 0.8092 | 0.3391 | 0.1273 | 0.016* | |
C13 | 0.6372 (4) | 0.3262 (4) | 0.1007 (3) | 0.0114 (8) | |
H13 | 0.6801 | 0.2693 | 0.0609 | 0.014* | |
C14 | 0.4888 (5) | 0.3704 (5) | 0.1195 (4) | 0.0103 (4) | |
N14 | 0.4103 (3) | 0.3316 (3) | 0.0820 (3) | 0.0122 (4) | |
H14C | 0.3208 | 0.3574 | 0.0954 | 0.015* | |
H14D | 0.4480 | 0.2800 | 0.0439 | 0.015* | |
C15 | 0.4343 (4) | 0.4506 (4) | 0.1793 (3) | 0.0124 (9) | |
H15 | 0.3378 | 0.4813 | 0.1930 | 0.015* | |
C16 | 0.5167 (4) | 0.4877 (4) | 0.2198 (3) | 0.0127 (8) | |
H16 | 0.4778 | 0.5418 | 0.2624 | 0.015* | |
N21 | 0.3527 (3) | 0.0502 (3) | 0.2988 (3) | 0.0124 (4) | |
H21 | 0.3015 | 0.0243 | 0.2737 | 0.015* | |
C22 | 0.4918 (4) | 0.0105 (4) | 0.2774 (3) | 0.0126 (9) | |
H22 | 0.5327 | −0.0428 | 0.2342 | 0.015* | |
C23 | 0.5721 (4) | 0.0488 (4) | 0.3193 (3) | 0.0119 (9) | |
H23 | 0.6688 | 0.0197 | 0.3060 | 0.014* | |
C24 | 0.5145 (4) | 0.1282 (5) | 0.3797 (4) | 0.0097 (4) | |
N24 | 0.5907 (3) | 0.1685 (3) | 0.4186 (3) | 0.0128 (4) | |
H24C | 0.6803 | 0.1441 | 0.4055 | 0.015* | |
H24D | 0.5513 | 0.2194 | 0.4571 | 0.015* | |
C25 | 0.3660 (4) | 0.1699 (4) | 0.3980 (3) | 0.0131 (9) | |
H25 | 0.3211 | 0.2261 | 0.4382 | 0.016* | |
C26 | 0.2936 (4) | 0.1276 (4) | 0.3572 (3) | 0.0142 (9) | |
H26 | 0.1968 | 0.1536 | 0.3702 | 0.017* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0051 (3) | 0.0058 (2) | 0.0068 (3) | −0.00186 (18) | −0.00046 (19) | −0.00176 (16) |
O11W | 0.0279 (12) | 0.0102 (11) | 0.0083 (9) | −0.0088 (9) | 0.0026 (8) | −0.0045 (8) |
O12W | 0.0152 (10) | 0.0302 (13) | 0.0087 (9) | −0.0165 (9) | −0.0027 (8) | 0.0016 (9) |
O13W | 0.0186 (10) | 0.0124 (10) | 0.0086 (9) | −0.0088 (8) | 0.0010 (8) | −0.0046 (8) |
O14W | 0.0106 (9) | 0.0195 (12) | 0.0090 (9) | −0.0082 (9) | −0.0008 (7) | −0.0025 (9) |
S11 | 0.0060 (3) | 0.0058 (4) | 0.0063 (3) | −0.0023 (3) | −0.0004 (3) | −0.0021 (3) |
O11 | 0.0138 (8) | 0.0065 (8) | 0.0111 (8) | 0.0009 (7) | −0.0020 (6) | −0.0022 (6) |
O12 | 0.0113 (12) | 0.0139 (13) | 0.0082 (11) | −0.0022 (10) | 0.0018 (9) | −0.0051 (9) |
O13 | 0.0099 (10) | 0.0111 (10) | 0.0116 (9) | −0.0034 (8) | −0.0009 (7) | −0.0050 (7) |
O14 | 0.0089 (9) | 0.0158 (11) | 0.0122 (9) | −0.0061 (8) | −0.0021 (7) | −0.0034 (8) |
S12 | 0.0060 (3) | 0.0064 (4) | 0.0065 (3) | −0.0013 (3) | −0.0009 (3) | −0.0024 (3) |
O15 | 0.0139 (8) | 0.0106 (9) | 0.0131 (8) | 0.0007 (7) | −0.0020 (6) | −0.0035 (7) |
O16 | 0.0130 (10) | 0.0173 (12) | 0.0103 (10) | −0.0083 (9) | −0.0020 (8) | −0.0033 (9) |
O17 | 0.0149 (10) | 0.0099 (11) | 0.0090 (9) | −0.0055 (8) | −0.0015 (7) | −0.0011 (8) |
O18 | 0.0083 (12) | 0.0158 (13) | 0.0115 (11) | −0.0041 (10) | 0.0015 (9) | −0.0093 (10) |
Fe2 | 0.0050 (3) | 0.0061 (2) | 0.0068 (3) | −0.00194 (18) | −0.00057 (19) | −0.00165 (16) |
O21W | 0.0234 (11) | 0.0149 (11) | 0.0083 (9) | −0.0122 (9) | −0.0003 (8) | −0.0043 (8) |
O22W | 0.0071 (9) | 0.0140 (12) | 0.0114 (10) | −0.0015 (9) | −0.0025 (7) | 0.0024 (9) |
O23W | 0.0172 (11) | 0.0073 (11) | 0.0079 (9) | −0.0056 (8) | 0.0011 (8) | −0.0026 (8) |
O24W | 0.0090 (9) | 0.0132 (10) | 0.0092 (9) | −0.0056 (8) | −0.0016 (7) | −0.0018 (8) |
S21 | 0.0063 (3) | 0.0061 (4) | 0.0079 (3) | −0.0013 (3) | 0.0002 (3) | −0.0027 (3) |
O21 | 0.0097 (8) | 0.0109 (8) | 0.0142 (8) | −0.0036 (7) | −0.0013 (6) | −0.0029 (6) |
O22 | 0.0089 (12) | 0.0144 (13) | 0.0100 (11) | −0.0035 (10) | 0.0007 (9) | −0.0069 (9) |
O23 | 0.0112 (10) | 0.0145 (12) | 0.0092 (9) | −0.0054 (8) | −0.0023 (8) | −0.0031 (8) |
O24 | 0.0137 (10) | 0.0080 (11) | 0.0092 (9) | −0.0054 (8) | −0.0019 (7) | −0.0016 (8) |
S22 | 0.0074 (3) | 0.0061 (4) | 0.0064 (3) | −0.0019 (3) | −0.0002 (3) | −0.0013 (3) |
O25 | 0.0109 (8) | 0.0082 (8) | 0.0138 (8) | 0.0000 (7) | −0.0011 (6) | −0.0021 (7) |
O26 | 0.0150 (10) | 0.0089 (11) | 0.0109 (9) | −0.0077 (8) | −0.0014 (7) | −0.0041 (8) |
O27 | 0.0159 (11) | 0.0164 (11) | 0.0092 (10) | −0.0093 (9) | −0.0031 (8) | −0.0034 (8) |
O28 | 0.0110 (13) | 0.0125 (12) | 0.0097 (11) | −0.0006 (10) | 0.0011 (9) | −0.0036 (9) |
N11 | 0.0072 (12) | 0.0110 (11) | 0.0127 (11) | −0.0029 (9) | −0.0049 (9) | −0.0020 (8) |
C12 | 0.0095 (18) | 0.014 (2) | 0.016 (2) | −0.0037 (15) | −0.0030 (15) | −0.0040 (16) |
C13 | 0.0061 (18) | 0.0085 (19) | 0.0155 (19) | 0.0012 (15) | 0.0007 (15) | −0.0043 (16) |
C14 | 0.007 (2) | 0.0102 (15) | 0.0089 (16) | −0.0030 (11) | −0.0019 (12) | 0.0020 (10) |
N14 | 0.0075 (17) | 0.0146 (13) | 0.0202 (15) | −0.0051 (10) | 0.0026 (11) | −0.0120 (9) |
C15 | 0.0080 (18) | 0.016 (2) | 0.0160 (19) | −0.0055 (16) | −0.0004 (15) | −0.0067 (17) |
C16 | 0.0101 (18) | 0.011 (2) | 0.0132 (19) | −0.0013 (14) | −0.0009 (14) | −0.0028 (16) |
N21 | 0.0093 (13) | 0.0135 (11) | 0.0148 (11) | −0.0047 (9) | −0.0046 (9) | −0.0029 (8) |
C22 | 0.0099 (18) | 0.013 (2) | 0.0130 (19) | −0.0015 (15) | 0.0014 (14) | −0.0053 (16) |
C23 | 0.0072 (17) | 0.015 (2) | 0.0160 (19) | −0.0062 (15) | 0.0009 (15) | −0.0064 (17) |
C24 | 0.0048 (19) | 0.0103 (16) | 0.0084 (16) | −0.0019 (11) | −0.0017 (11) | 0.0019 (10) |
N24 | 0.0084 (17) | 0.0144 (13) | 0.0210 (15) | −0.0053 (10) | 0.0022 (11) | −0.0117 (9) |
C25 | 0.0065 (18) | 0.013 (2) | 0.018 (2) | 0.0000 (15) | 0.0014 (16) | −0.0079 (17) |
C26 | 0.0088 (18) | 0.019 (2) | 0.016 (2) | −0.0043 (16) | −0.0002 (15) | −0.0079 (17) |
Geometric parameters (Å, º) top
Fe1—O11 | 1.9401 (18) | S21—O23 | 1.446 (2) |
Fe1—O15 | 1.9451 (18) | S21—O22 | 1.470 (2) |
Fe1—O11W | 1.995 (2) | S21—O24 | 1.488 (2) |
Fe1—O12W | 2.011 (2) | S21—O21 | 1.5034 (18) |
Fe1—O14W | 2.015 (2) | S22—O28 | 1.460 (2) |
Fe1—O13W | 2.031 (2) | S22—O27 | 1.462 (3) |
O11W—H11A | 0.828 (18) | S22—O26 | 1.484 (2) |
O11W—H11B | 0.832 (18) | S22—O25 | 1.4961 (18) |
O12W—H12A | 0.852 (19) | N11—C12 | 1.330 (5) |
O12W—H12B | 0.804 (18) | N11—C16 | 1.371 (5) |
O13W—H13A | 0.868 (18) | N11—H11 | 0.8800 |
O13W—H13B | 0.836 (19) | C12—C13 | 1.341 (5) |
O14W—H14A | 0.867 (19) | C12—H12 | 0.9500 |
O14W—H14B | 0.835 (18) | C13—C14 | 1.456 (6) |
S11—O12 | 1.462 (2) | C13—H13 | 0.9500 |
S11—O13 | 1.467 (3) | C14—N14 | 1.332 (2) |
S11—O14 | 1.481 (2) | C14—C15 | 1.372 (6) |
S11—O11 | 1.4964 (18) | N14—H14C | 0.8800 |
S12—O17 | 1.453 (2) | N14—H14D | 0.8800 |
S12—O18 | 1.466 (2) | C15—C16 | 1.377 (5) |
S12—O16 | 1.488 (3) | C15—H15 | 0.9500 |
S12—O15 | 1.4975 (18) | C16—H16 | 0.9500 |
Fe2—O21 | 1.9465 (18) | N21—C26 | 1.335 (5) |
Fe2—O25 | 1.9514 (18) | N21—C22 | 1.368 (5) |
Fe2—O22W | 2.003 (2) | N21—H21 | 0.8800 |
Fe2—O23W | 2.009 (2) | C22—C23 | 1.381 (5) |
Fe2—O21W | 2.0171 (19) | C22—H22 | 0.9500 |
Fe2—O24W | 2.036 (2) | C23—C24 | 1.372 (6) |
O21W—H21A | 0.867 (18) | C23—H23 | 0.9500 |
O21W—H21B | 0.838 (19) | C24—N24 | 1.337 (2) |
O22W—H22A | 0.808 (18) | C24—C25 | 1.456 (6) |
O22W—H22B | 0.887 (18) | N24—H24C | 0.8800 |
O23W—H23A | 0.846 (18) | N24—H24D | 0.8800 |
O23W—H23B | 0.786 (18) | C25—C26 | 1.340 (6) |
O24W—H24A | 0.773 (18) | C25—H25 | 0.9500 |
O24W—H24B | 0.863 (18) | C26—H26 | 0.9500 |
| | | |
O11—Fe1—O15 | 177.57 (7) | Fe2—O23W—H23A | 120.9 (19) |
O11—Fe1—O11W | 92.71 (8) | Fe2—O23W—H23B | 109 (2) |
O15—Fe1—O11W | 85.35 (9) | H23A—O23W—H23B | 120 (3) |
O11—Fe1—O12W | 93.61 (8) | Fe2—O24W—H24A | 113 (2) |
O15—Fe1—O12W | 87.83 (8) | Fe2—O24W—H24B | 122.9 (17) |
O11W—Fe1—O12W | 89.22 (9) | H24A—O24W—H24B | 112 (3) |
O11—Fe1—O14W | 89.35 (9) | O23—S21—O22 | 110.76 (15) |
O15—Fe1—O14W | 89.26 (9) | O23—S21—O24 | 110.81 (13) |
O11W—Fe1—O14W | 92.19 (7) | O22—S21—O24 | 111.56 (15) |
O12W—Fe1—O14W | 176.66 (9) | O23—S21—O21 | 109.73 (11) |
O11—Fe1—O13W | 85.48 (8) | O22—S21—O21 | 108.90 (11) |
O15—Fe1—O13W | 96.45 (8) | O24—S21—O21 | 104.89 (12) |
O11W—Fe1—O13W | 178.18 (8) | S21—O21—Fe2 | 144.75 (10) |
O12W—Fe1—O13W | 91.11 (7) | O28—S22—O27 | 110.94 (16) |
O14W—Fe1—O13W | 87.57 (8) | O28—S22—O26 | 109.94 (15) |
Fe1—O11W—H11A | 127 (2) | O27—S22—O26 | 110.83 (13) |
Fe1—O11W—H11B | 109 (2) | O28—S22—O25 | 110.10 (12) |
H11A—O11W—H11B | 123 (3) | O27—S22—O25 | 108.87 (12) |
Fe1—O12W—H12A | 131.0 (19) | O26—S22—O25 | 106.04 (12) |
Fe1—O12W—H12B | 116 (2) | S22—O25—Fe2 | 147.48 (10) |
H12A—O12W—H12B | 113 (3) | C12—N11—C16 | 121.33 (17) |
Fe1—O13W—H13A | 116.6 (17) | C12—N11—H11 | 119.3 |
Fe1—O13W—H13B | 131 (2) | C16—N11—H11 | 119.3 |
H13A—O13W—H13B | 95 (3) | N11—C12—C13 | 122.1 (4) |
Fe1—O14W—H14A | 124.4 (18) | N11—C12—H12 | 119.0 |
Fe1—O14W—H14B | 123 (2) | C13—C12—H12 | 119.0 |
H14A—O14W—H14B | 104 (3) | C12—C13—C14 | 119.0 (4) |
O12—S11—O13 | 110.68 (16) | C12—C13—H13 | 120.5 |
O12—S11—O14 | 110.09 (16) | C14—C13—H13 | 120.5 |
O13—S11—O14 | 111.55 (13) | N14—C14—C15 | 121.9 (5) |
O12—S11—O11 | 109.71 (11) | N14—C14—C13 | 120.9 (5) |
O13—S11—O11 | 105.85 (12) | C15—C14—C13 | 117.21 (18) |
O14—S11—O11 | 108.85 (12) | C14—N14—H14C | 120.0 |
S11—O11—Fe1 | 148.86 (10) | C14—N14—H14D | 120.0 |
O17—S12—O18 | 110.48 (14) | H14C—N14—H14D | 120.0 |
O17—S12—O16 | 110.52 (12) | C14—C15—C16 | 121.3 (4) |
O18—S12—O16 | 111.59 (16) | C14—C15—H15 | 119.3 |
O17—S12—O15 | 106.79 (12) | C16—C15—H15 | 119.3 |
O18—S12—O15 | 108.82 (12) | N11—C16—C15 | 119.1 (4) |
O16—S12—O15 | 108.50 (12) | N11—C16—H16 | 120.5 |
S12—O15—Fe1 | 148.09 (10) | C15—C16—H16 | 120.5 |
O21—Fe2—O25 | 178.14 (7) | C26—N21—C22 | 120.97 (17) |
O21—Fe2—O22W | 92.16 (8) | C26—N21—H21 | 119.5 |
O25—Fe2—O22W | 86.06 (8) | C22—N21—H21 | 119.5 |
O21—Fe2—O23W | 91.07 (8) | N21—C22—C23 | 119.4 (4) |
O25—Fe2—O23W | 88.43 (8) | N21—C22—H22 | 120.3 |
O22W—Fe2—O23W | 92.40 (7) | C23—C22—H22 | 120.3 |
O21—Fe2—O21W | 93.49 (8) | C24—C23—C22 | 121.1 (4) |
O25—Fe2—O21W | 87.12 (8) | C24—C23—H23 | 119.5 |
O22W—Fe2—O21W | 90.87 (8) | C22—C23—H23 | 119.5 |
O23W—Fe2—O21W | 174.29 (8) | N24—C24—C23 | 121.7 (5) |
O21—Fe2—O24W | 85.32 (8) | N24—C24—C25 | 120.8 (5) |
O25—Fe2—O24W | 96.46 (8) | C23—C24—C25 | 117.40 (18) |
O22W—Fe2—O24W | 177.46 (8) | C24—N24—H24C | 120.0 |
O23W—Fe2—O24W | 87.98 (8) | C24—N24—H24D | 120.0 |
O21W—Fe2—O24W | 88.96 (7) | H24C—N24—H24D | 120.0 |
Fe2—O21W—H21A | 121.4 (17) | C26—C25—C24 | 118.8 (4) |
Fe2—O21W—H21B | 129 (2) | C26—C25—H25 | 120.6 |
H21A—O21W—H21B | 104 (3) | C24—C25—H25 | 120.6 |
Fe2—O22W—H22A | 133.4 (19) | N21—C26—C25 | 122.4 (4) |
Fe2—O22W—H22B | 120.1 (18) | N21—C26—H26 | 118.8 |
H22A—O22W—H22B | 104 (3) | C25—C26—H26 | 118.8 |
| | | |
O12—S11—O11—Fe1 | 36.7 (3) | C12—C13—C14—N14 | −179.6 (4) |
O13—S11—O11—Fe1 | 156.16 (19) | C12—C13—C14—C15 | −1.1 (8) |
O14—S11—O11—Fe1 | −83.8 (2) | N14—C14—C15—C16 | 178.5 (4) |
O17—S12—O15—Fe1 | −165.54 (18) | C13—C14—C15—C16 | 0.0 (8) |
O18—S12—O15—Fe1 | −46.3 (2) | C12—N11—C16—C15 | −1.6 (7) |
O16—S12—O15—Fe1 | 75.3 (2) | C14—C15—C16—N11 | 1.4 (7) |
O23—S21—O21—Fe2 | 74.87 (19) | C26—N21—C22—C23 | 1.5 (7) |
O22—S21—O21—Fe2 | −46.5 (2) | N21—C22—C23—C24 | −1.4 (7) |
O24—S21—O21—Fe2 | −166.06 (17) | C22—C23—C24—N24 | −178.4 (4) |
O28—S22—O25—Fe2 | 46.8 (2) | C22—C23—C24—C25 | 0.1 (8) |
O27—S22—O25—Fe2 | −75.0 (2) | N24—C24—C25—C26 | 179.7 (4) |
O26—S22—O25—Fe2 | 165.68 (18) | C23—C24—C25—C26 | 1.1 (8) |
C16—N11—C12—C13 | 0.5 (8) | C22—N21—C26—C25 | −0.3 (8) |
N11—C12—C13—C14 | 0.8 (7) | C24—C25—C26—N21 | −1.1 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11W—H11A···O12i | 0.83 (2) | 1.93 (2) | 2.726 (4) | 162 (3) |
O11W—H11B···O26ii | 0.83 (2) | 1.77 (2) | 2.589 (3) | 169 (3) |
O12W—H12A···O16iii | 0.85 (2) | 1.81 (2) | 2.662 (3) | 178 (3) |
O12W—H12B···O27ii | 0.80 (2) | 1.86 (2) | 2.662 (3) | 175 (3) |
O13W—H13A···O24iv | 0.87 (2) | 1.80 (2) | 2.664 (3) | 173 (2) |
O13W—H13B···O27v | 0.84 (2) | 1.85 (2) | 2.672 (3) | 169 (3) |
O14W—H14A···O18ii | 0.87 (2) | 1.91 (2) | 2.743 (3) | 160 (3) |
O14W—H14B···O23iv | 0.84 (2) | 1.81 (2) | 2.627 (3) | 168 (3) |
O21W—H21A···O16ii | 0.867 (18) | 1.830 (18) | 2.695 (3) | 175 (3) |
O21W—H21B···O13vi | 0.838 (19) | 1.885 (19) | 2.720 (3) | 174 (3) |
O22W—H22A···O22iv | 0.808 (18) | 1.93 (2) | 2.719 (4) | 166 (3) |
O22W—H22B···O17ii | 0.887 (18) | 1.716 (19) | 2.589 (3) | 167 (3) |
O23W—H23A···O28vii | 0.846 (18) | 1.941 (19) | 2.773 (3) | 167 (3) |
O23W—H23B···O14iv | 0.786 (18) | 1.838 (19) | 2.599 (3) | 163 (3) |
O24W—H24A···O13iv | 0.773 (18) | 1.948 (19) | 2.717 (3) | 172 (3) |
O24W—H24B···O24viii | 0.863 (18) | 1.850 (19) | 2.698 (3) | 167 (2) |
N11—H11···O14 | 0.88 | 2.17 | 2.856 (3) | 135 |
N11—H11···O23iv | 0.88 | 2.23 | 2.880 (3) | 131 |
N14—H14C···O12vi | 0.88 | 2.10 | 2.945 (5) | 161 |
N14—H14D···O18ix | 0.88 | 2.14 | 2.994 (4) | 164 |
C15—H15···O13vi | 0.95 | 2.55 | 3.439 (5) | 155 |
C16—H16···O23iv | 0.95 | 2.56 | 3.050 (5) | 113 |
N21—H21···O17x | 0.88 | 2.40 | 3.006 (4) | 126 |
N21—H21···O26ix | 0.88 | 2.39 | 2.980 (4) | 125 |
C22—H22···O17x | 0.95 | 2.54 | 3.083 (5) | 117 |
N24—H24C···O28xi | 0.88 | 2.09 | 2.938 (5) | 162 |
N24—H24D···O22 | 0.88 | 2.19 | 3.036 (4) | 162 |
C25—H25···O24 | 0.95 | 2.59 | 3.464 (5) | 154 |
C26—H26···O26ix | 0.95 | 2.43 | 3.022 (5) | 120 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x+2, −y+2, −z; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z; (vi) x−1, y, z; (vii) −x, −y+2, −z+1; (viii) −x, −y+1, −z+1; (ix) x, y−1, z; (x) −x+1, −y+1, −z; (xi) x+1, y−1, z. |
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