Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810200976X/na0136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136VIIsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136VIIIsup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810200976X/na0136IXsup10.hkl |
CCDC references: 195783; 195784; 195785; 195786; 195787; 195788; 195789; 195790; 195791
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXS97 (Sheldrick, 1997) for (VI). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXL97 (Sheldrick, 1997) for (VI). Molecular graphics: PLATON (Spek, 2002) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); ORTEP (Johnson, 1976), PLATON (Spek, 2001) for (VI). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX); SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for (VI).
C12H9FeO4·C2H8N | F(000) = 1328 |
Mr = 319.14 | Dx = 1.532 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3330 reflections |
a = 30.9616 (7) Å | θ = 2.7–27.5° |
b = 7.8147 (2) Å | µ = 1.10 mm−1 |
c = 12.1521 (3) Å | T = 150 K |
β = 109.7090 (12)° | Plate, red |
V = 2768.02 (12) Å3 | 0.22 × 0.20 × 0.12 mm |
Z = 8 |
Kappa-CCD diffractometer | 3166 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→40 |
Tmin = 0.794, Tmax = 0.879 | k = 0→10 |
15103 measured reflections | l = −15→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0222P)2 + 2.8956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3166 reflections | Δρmax = 0.37 e Å−3 |
185 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (2) |
C12H9FeO4·C2H8N | V = 2768.02 (12) Å3 |
Mr = 319.14 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.9616 (7) Å | µ = 1.10 mm−1 |
b = 7.8147 (2) Å | T = 150 K |
c = 12.1521 (3) Å | 0.22 × 0.20 × 0.12 mm |
β = 109.7090 (12)° |
Kappa-CCD diffractometer | 3166 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2798 reflections with I > 2σ(I) |
Tmin = 0.794, Tmax = 0.879 | Rint = 0.037 |
15103 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.37 e Å−3 |
3166 reflections | Δρmin = −0.40 e Å−3 |
185 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.073283 (7) | 0.23380 (3) | 0.063813 (17) | 0.01601 (9) | |
O11 | 0.11059 (4) | −0.21272 (17) | 0.06292 (13) | 0.0335 (3) | |
O12 | 0.16924 (4) | −0.06958 (17) | 0.03685 (11) | 0.0296 (3) | |
O21 | 0.19647 (4) | 0.31124 (17) | 0.25411 (11) | 0.0291 (3) | |
O22 | 0.16856 (4) | 0.56051 (15) | 0.17781 (11) | 0.0278 (3) | |
C11 | 0.09509 (5) | 0.0543 (2) | −0.02694 (13) | 0.0191 (3) | |
C12 | 0.10535 (6) | 0.2210 (2) | −0.05816 (14) | 0.0230 (3) | |
C13 | 0.06356 (6) | 0.3133 (2) | −0.10393 (14) | 0.0278 (4) | |
C14 | 0.02720 (6) | 0.2027 (2) | −0.10166 (14) | 0.0265 (4) | |
C15 | 0.04633 (5) | 0.0433 (2) | −0.05385 (13) | 0.0217 (3) | |
C16 | 0.12893 (5) | −0.0801 (2) | 0.02701 (14) | 0.0215 (3) | |
C21 | 0.11681 (5) | 0.3551 (2) | 0.20673 (13) | 0.0195 (3) | |
C22 | 0.07472 (5) | 0.4493 (2) | 0.15962 (14) | 0.0225 (3) | |
C23 | 0.03824 (6) | 0.3403 (2) | 0.16286 (14) | 0.0258 (4) | |
C24 | 0.05739 (6) | 0.1807 (2) | 0.21129 (13) | 0.0254 (4) | |
C25 | 0.10567 (6) | 0.1893 (2) | 0.23841 (13) | 0.0228 (3) | |
C26 | 0.16358 (5) | 0.4120 (2) | 0.21347 (13) | 0.0197 (3) | |
N1 | 0.25184 (5) | 0.53407 (19) | 0.13712 (12) | 0.0249 (3) | |
C1 | 0.22769 (6) | 0.5521 (3) | 0.00978 (16) | 0.0313 (4) | |
C2 | 0.28054 (6) | 0.3796 (3) | 0.16778 (17) | 0.0346 (4) | |
H11 | 0.1314 | −0.2811 | 0.0995 | 0.050* | |
H12 | 0.1351 | 0.2634 | −0.0498 | 0.028* | |
H13 | 0.0604 | 0.4281 | −0.1312 | 0.033* | |
H14 | −0.0045 | 0.2312 | −0.1278 | 0.032* | |
H15 | 0.0299 | −0.0534 | −0.0418 | 0.026* | |
H22 | 0.0717 | 0.5636 | 0.1314 | 0.027* | |
H23 | 0.0066 | 0.3694 | 0.1371 | 0.031* | |
H24 | 0.0407 | 0.0846 | 0.2234 | 0.030* | |
H25 | 0.1269 | 0.1001 | 0.2719 | 0.027* | |
H1A | 0.2700 | 0.6287 | 0.1638 | 0.030* | |
H1B | 0.2305 | 0.5307 | 0.1745 | 0.030* | |
H1C | 0.2503 | 0.5610 | −0.0304 | 0.047* | |
H1D | 0.2087 | 0.6555 | −0.0053 | 0.047* | |
H1E | 0.2082 | 0.4518 | −0.0193 | 0.047* | |
H2A | 0.2612 | 0.2779 | 0.1423 | 0.052* | |
H2B | 0.2960 | 0.3752 | 0.2526 | 0.052* | |
H2C | 0.3036 | 0.3827 | 0.1288 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01708 (13) | 0.01735 (13) | 0.01438 (13) | 0.00061 (8) | 0.00634 (9) | 0.00050 (8) |
O11 | 0.0233 (6) | 0.0232 (7) | 0.0537 (8) | 0.0039 (5) | 0.0127 (6) | 0.0136 (6) |
O12 | 0.0203 (6) | 0.0303 (7) | 0.0405 (7) | 0.0035 (5) | 0.0134 (5) | 0.0026 (5) |
O21 | 0.0208 (6) | 0.0267 (6) | 0.0355 (7) | 0.0041 (5) | 0.0041 (5) | 0.0060 (5) |
O22 | 0.0214 (5) | 0.0190 (6) | 0.0424 (7) | −0.0002 (5) | 0.0100 (5) | 0.0054 (5) |
C11 | 0.0201 (7) | 0.0216 (8) | 0.0168 (7) | 0.0013 (6) | 0.0077 (6) | −0.0020 (6) |
C12 | 0.0291 (8) | 0.0245 (9) | 0.0211 (8) | 0.0022 (7) | 0.0159 (7) | 0.0026 (6) |
C13 | 0.0400 (10) | 0.0280 (9) | 0.0188 (8) | 0.0092 (8) | 0.0144 (7) | 0.0069 (7) |
C14 | 0.0243 (8) | 0.0345 (10) | 0.0173 (8) | 0.0075 (7) | 0.0026 (6) | −0.0017 (7) |
C15 | 0.0203 (7) | 0.0256 (8) | 0.0179 (7) | 0.0003 (6) | 0.0046 (6) | −0.0046 (6) |
C16 | 0.0226 (8) | 0.0202 (8) | 0.0227 (8) | 0.0010 (6) | 0.0089 (6) | −0.0026 (6) |
C21 | 0.0209 (7) | 0.0209 (8) | 0.0170 (7) | −0.0026 (6) | 0.0068 (6) | −0.0032 (6) |
C22 | 0.0232 (8) | 0.0214 (8) | 0.0253 (8) | 0.0009 (6) | 0.0115 (6) | −0.0049 (6) |
C23 | 0.0222 (8) | 0.0339 (10) | 0.0252 (8) | −0.0015 (7) | 0.0131 (7) | −0.0073 (7) |
C24 | 0.0294 (8) | 0.0325 (10) | 0.0169 (7) | −0.0106 (7) | 0.0113 (6) | −0.0024 (7) |
C25 | 0.0272 (8) | 0.0248 (8) | 0.0152 (7) | −0.0036 (7) | 0.0056 (6) | 0.0011 (6) |
C26 | 0.0200 (7) | 0.0198 (8) | 0.0180 (7) | −0.0006 (6) | 0.0048 (6) | −0.0023 (6) |
N1 | 0.0239 (7) | 0.0235 (7) | 0.0293 (7) | −0.0062 (6) | 0.0115 (6) | −0.0061 (6) |
C1 | 0.0283 (9) | 0.0323 (10) | 0.0317 (9) | −0.0008 (7) | 0.0082 (7) | 0.0008 (8) |
C2 | 0.0335 (10) | 0.0296 (10) | 0.0379 (10) | 0.0004 (8) | 0.0084 (8) | 0.0028 (8) |
Fe1—C11 | 2.0353 (15) | C14—H14 | 0.95 |
Fe1—C21 | 2.0378 (15) | C15—H15 | 0.95 |
Fe1—C15 | 2.0379 (16) | C21—C25 | 1.426 (2) |
Fe1—C22 | 2.0392 (16) | C21—C22 | 1.437 (2) |
Fe1—C12 | 2.0459 (15) | C21—C26 | 1.490 (2) |
Fe1—C25 | 2.0477 (15) | C22—C23 | 1.426 (2) |
Fe1—C23 | 2.0492 (16) | C22—H22 | 0.95 |
Fe1—C14 | 2.0501 (16) | C23—C24 | 1.421 (3) |
Fe1—C13 | 2.0538 (16) | C23—H23 | 0.95 |
Fe1—C24 | 2.0545 (15) | C24—C25 | 1.420 (2) |
O11—C16 | 1.324 (2) | C24—H24 | 0.95 |
O11—H11 | 0.84 | C25—H25 | 0.95 |
O12—C16 | 1.2157 (19) | N1—C2 | 1.471 (2) |
O21—C26 | 1.2495 (19) | N1—C1 | 1.481 (2) |
O22—C26 | 1.267 (2) | N1—H1A | 0.92 |
C11—C12 | 1.423 (2) | N1—H1B | 0.92 |
C11—C15 | 1.435 (2) | C1—H1C | 0.98 |
C11—C16 | 1.472 (2) | C1—H1D | 0.98 |
C12—C13 | 1.421 (2) | C1—H1E | 0.98 |
C12—H12 | 0.95 | C2—H2A | 0.98 |
C13—C14 | 1.427 (3) | C2—H2B | 0.98 |
C13—H13 | 0.95 | C2—H2C | 0.98 |
C14—C15 | 1.418 (2) | ||
C11—Fe1—C21 | 122.52 (6) | C15—C14—Fe1 | 69.25 (9) |
C11—Fe1—C15 | 41.27 (6) | C13—C14—Fe1 | 69.80 (9) |
C21—Fe1—C15 | 159.14 (7) | C15—C14—H14 | 125.8 |
C11—Fe1—C22 | 158.62 (6) | C13—C14—H14 | 125.8 |
C21—Fe1—C22 | 41.27 (6) | Fe1—C14—H14 | 126.8 |
C15—Fe1—C22 | 158.26 (6) | C14—C15—C11 | 107.61 (15) |
C11—Fe1—C12 | 40.80 (6) | C14—C15—Fe1 | 70.17 (9) |
C21—Fe1—C12 | 107.28 (7) | C11—C15—Fe1 | 69.27 (9) |
C15—Fe1—C12 | 68.90 (7) | C14—C15—H15 | 126.2 |
C22—Fe1—C12 | 122.10 (7) | C11—C15—H15 | 126.2 |
C11—Fe1—C25 | 107.97 (7) | Fe1—C15—H15 | 125.9 |
C21—Fe1—C25 | 40.87 (6) | O12—C16—O11 | 124.09 (15) |
C15—Fe1—C25 | 123.00 (7) | O12—C16—C11 | 123.26 (15) |
C22—Fe1—C25 | 68.89 (7) | O11—C16—C11 | 112.65 (13) |
C12—Fe1—C25 | 123.69 (7) | C25—C21—C22 | 107.67 (14) |
C11—Fe1—C23 | 159.45 (7) | C25—C21—C26 | 125.09 (14) |
C21—Fe1—C23 | 68.87 (6) | C22—C21—C26 | 127.08 (15) |
C15—Fe1—C23 | 122.43 (7) | C25—C21—Fe1 | 69.94 (9) |
C22—Fe1—C23 | 40.82 (7) | C22—C21—Fe1 | 69.42 (9) |
C12—Fe1—C23 | 158.09 (7) | C26—C21—Fe1 | 122.45 (10) |
C25—Fe1—C23 | 68.39 (7) | C23—C22—C21 | 107.66 (15) |
C11—Fe1—C14 | 68.61 (6) | C23—C22—Fe1 | 69.97 (9) |
C21—Fe1—C14 | 158.83 (7) | C21—C22—Fe1 | 69.31 (9) |
C15—Fe1—C14 | 40.58 (7) | C23—C22—H22 | 126.2 |
C22—Fe1—C14 | 122.12 (7) | C21—C22—H22 | 126.2 |
C12—Fe1—C14 | 68.34 (7) | Fe1—C22—H22 | 126.1 |
C25—Fe1—C14 | 158.73 (7) | C24—C23—C22 | 108.19 (14) |
C23—Fe1—C14 | 107.04 (7) | C24—C23—Fe1 | 69.94 (9) |
C11—Fe1—C13 | 68.59 (7) | C22—C23—Fe1 | 69.21 (9) |
C21—Fe1—C13 | 122.60 (7) | C24—C23—H23 | 125.9 |
C15—Fe1—C13 | 68.67 (7) | C22—C23—H23 | 125.9 |
C22—Fe1—C13 | 106.53 (7) | Fe1—C23—H23 | 126.5 |
C12—Fe1—C13 | 40.55 (7) | C25—C24—C23 | 108.30 (15) |
C25—Fe1—C13 | 159.46 (7) | C25—C24—Fe1 | 69.49 (9) |
C23—Fe1—C13 | 122.05 (7) | C23—C24—Fe1 | 69.54 (9) |
C14—Fe1—C13 | 40.69 (7) | C25—C24—H24 | 125.8 |
C11—Fe1—C24 | 123.66 (7) | C23—C24—H24 | 125.8 |
C21—Fe1—C24 | 68.57 (6) | Fe1—C24—H24 | 126.7 |
C15—Fe1—C24 | 107.61 (7) | C24—C25—C21 | 108.18 (15) |
C22—Fe1—C24 | 68.55 (7) | C24—C25—Fe1 | 70.01 (9) |
C12—Fe1—C24 | 160.00 (7) | C21—C25—Fe1 | 69.19 (9) |
C25—Fe1—C24 | 40.50 (7) | C24—C25—H25 | 125.9 |
C23—Fe1—C24 | 40.51 (7) | C21—C25—H25 | 125.9 |
C14—Fe1—C24 | 122.65 (7) | Fe1—C25—H25 | 126.5 |
C13—Fe1—C24 | 158.26 (7) | O21—C26—O22 | 122.38 (14) |
C16—O11—H11 | 109.5 | O21—C26—C21 | 118.76 (15) |
C12—C11—C15 | 107.85 (14) | O22—C26—C21 | 118.86 (14) |
C12—C11—C16 | 125.64 (14) | C2—N1—C1 | 113.08 (14) |
C15—C11—C16 | 126.48 (15) | C2—N1—H1A | 109.0 |
C12—C11—Fe1 | 70.00 (9) | C1—N1—H1A | 109.0 |
C15—C11—Fe1 | 69.46 (9) | C2—N1—H1B | 109.0 |
C16—C11—Fe1 | 124.52 (11) | C1—N1—H1B | 109.0 |
C13—C12—C11 | 108.26 (15) | H1A—N1—H1B | 107.8 |
C13—C12—Fe1 | 70.02 (9) | N1—C1—H1C | 109.5 |
C11—C12—Fe1 | 69.20 (9) | N1—C1—H1D | 109.5 |
C13—C12—H12 | 125.9 | H1C—C1—H1D | 109.5 |
C11—C12—H12 | 125.9 | N1—C1—H1E | 109.5 |
Fe1—C12—H12 | 126.5 | H1C—C1—H1E | 109.5 |
C12—C13—C14 | 107.80 (16) | H1D—C1—H1E | 109.5 |
C12—C13—Fe1 | 69.43 (9) | N1—C2—H2A | 109.5 |
C14—C13—Fe1 | 69.52 (9) | N1—C2—H2B | 109.5 |
C12—C13—H13 | 126.1 | H2A—C2—H2B | 109.5 |
C14—C13—H13 | 126.1 | N1—C2—H2C | 109.5 |
Fe1—C13—H13 | 126.5 | H2A—C2—H2C | 109.5 |
C15—C14—C13 | 108.48 (14) | H2B—C2—H2C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O22i | 0.84 | 1.74 | 2.573 (2) | 172 |
N1—H1A···O21ii | 0.92 | 1.85 | 2.752 (2) | 168 |
N1—H1B···O21 | 0.92 | 2.38 | 3.104 (2) | 135 |
N1—H1B···O22 | 0.92 | 1.95 | 2.792 (2) | 152 |
C2—H2B···O12ii | 0.95 | 2.46 | 3.420 (2) | 168 |
C22—H22···O11iii | 0.95 | 2.42 | 3.236 (2) | 143 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z. |
C12H9FeO4·C6H13N2 | Z = 2 |
Mr = 386.23 | F(000) = 404 |
Triclinic, P1 | Dx = 1.556 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4666 (3) Å | Cell parameters from 2733 reflections |
b = 10.7846 (5) Å | θ = 2.9–25.1° |
c = 11.3184 (6) Å | µ = 0.94 mm−1 |
α = 104.897 (2)° | T = 150 K |
β = 99.153 (2)° | Plate, colourless |
γ = 105.238 (2)° | 0.16 × 0.16 × 0.01 mm |
V = 824.32 (7) Å3 |
Kappa-CCD diffractometer | 2910 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2244 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ scans, and ω scans with κ offsets | θmax = 25.1°, θmin = 2.9° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→8 |
Tmin = 0.864, Tmax = 0.995 | k = −12→12 |
7460 measured reflections | l = −13→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2)P)2 + 0.1851P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2910 reflections | Δρmax = 0.31 e Å−3 |
229 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.006 (2) |
C12H9FeO4·C6H13N2 | γ = 105.238 (2)° |
Mr = 386.23 | V = 824.32 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4666 (3) Å | Mo Kα radiation |
b = 10.7846 (5) Å | µ = 0.94 mm−1 |
c = 11.3184 (6) Å | T = 150 K |
α = 104.897 (2)° | 0.16 × 0.16 × 0.01 mm |
β = 99.153 (2)° |
Kappa-CCD diffractometer | 2910 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2244 reflections with I > 2σ(I) |
Tmin = 0.864, Tmax = 0.995 | Rint = 0.051 |
7460 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.31 e Å−3 |
2910 reflections | Δρmin = −0.33 e Å−3 |
229 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 4.4254 (0.0092) x - 2.1637 (0.0152) y + 7.6272 (0.0125) z = 3.0620 (0.0039) * 0.0011 (0.0007) C11 * -0.0041 (0.0024) C16 * 0.0014 (0.0008) O11 * 0.0015 (0.0009) O12 Rms deviation of fitted atoms = 0.0023 4.5076 (0.0055) x - 3.7218 (0.0151) y + 7.7967 (0.0077) z = 2.7193 (0.0039) Angle to previous plane (with approximate e.s.d.) = 8.62 (0.19) * 0.0122 (0.0024) C11 * 0.0077 (0.0019) C12 * -0.0076 (0.0019) C13 * -0.0072 (0.0020) C14 * 0.0079 (0.0020) C15 * -0.0130 (0.0015) C16 Rms deviation of fitted atoms = 0.0096 - 4.5981 (0.0056) x + 4.5159 (0.0147) y - 7.6925 (0.0078) z = 0.7516 (0.0043) Angle to previous plane (with approximate e.s.d.) = 4.62 (0.16) * 0.0090 (0.0025) C21 * 0.0026 (0.0019) C22 * -0.0014 (0.0020) C23 * -0.0086 (0.0020) C24 * 0.0072 (0.0020) C25 * -0.0090 (0.0016) C26 Rms deviation of fitted atoms = 0.0070 - 4.3773 (0.0090) x + 6.0686 (0.0131) y - 7.7568 (0.0126) z = 1.1857 (0.0067) Angle to previous plane (with approximate e.s.d.) = 9.63 (1/5) * 0.0018 (0.0007) C21 * -0.0065 (0.0024) C26 * 0.0022 (0.0008) O21 * 0.0024 (0.0009) O22 Rms deviation of fitted atoms = 0.0037 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.32110 (6) | 0.24425 (4) | 0.06814 (4) | 0.02345 (17) | |
O11 | 0.1571 (3) | 0.1644 (2) | 0.35714 (19) | 0.0291 (5) | |
O12 | 0.2241 (4) | 0.3854 (2) | 0.3810 (2) | 0.0393 (6) | |
O21 | 0.5234 (3) | 0.3261 (2) | −0.1933 (2) | 0.0332 (5) | |
O22 | 0.3650 (3) | 0.1045 (2) | −0.2774 (2) | 0.0431 (6) | |
C11 | 0.3810 (4) | 0.2606 (3) | 0.2544 (3) | 0.0229 (6) | |
C12 | 0.4036 (4) | 0.1373 (3) | 0.1820 (3) | 0.0253 (7) | |
C13 | 0.5444 (4) | 0.1735 (3) | 0.1159 (3) | 0.0270 (7) | |
C14 | 0.6095 (4) | 0.3160 (3) | 0.1463 (3) | 0.0301 (7) | |
C15 | 0.5095 (4) | 0.3707 (3) | 0.2322 (3) | 0.0284 (7) | |
C21 | 0.2601 (4) | 0.2331 (3) | −0.1175 (3) | 0.0247 (7) | |
C22 | 0.2519 (4) | 0.3579 (3) | −0.0385 (3) | 0.0262 (7) | |
C23 | 0.1093 (4) | 0.3244 (3) | 0.0276 (3) | 0.0315 (7) | |
C24 | 0.0317 (5) | 0.1824 (3) | −0.0084 (3) | 0.0330 (8) | |
C25 | 0.1227 (4) | 0.1251 (3) | −0.0986 (3) | 0.0295 (7) | |
C16 | 0.2454 (4) | 0.2752 (3) | 0.3366 (3) | 0.0269 (7) | |
C26 | 0.3911 (4) | 0.2172 (3) | −0.2028 (3) | 0.0264 (7) | |
N1 | −0.0527 (3) | 0.2175 (2) | 0.5114 (2) | 0.0233 (5) | |
N2 | −0.2646 (3) | 0.2748 (2) | 0.6570 (2) | 0.0241 (6) | |
C31 | −0.1138 (4) | 0.1069 (3) | 0.5663 (3) | 0.0250 (7) | |
C32 | −0.2368 (5) | 0.1432 (3) | 0.6579 (3) | 0.0289 (7) | |
C41 | −0.2242 (4) | 0.2338 (3) | 0.4390 (3) | 0.0286 (7) | |
C42 | −0.3560 (4) | 0.2656 (3) | 0.5268 (3) | 0.0276 (7) | |
C51 | 0.0553 (4) | 0.3454 (3) | 0.6147 (3) | 0.0279 (7) | |
C52 | −0.0765 (4) | 0.3825 (3) | 0.7004 (3) | 0.0281 (7) | |
H11 | 0.0862 | 0.1809 | 0.4057 | 0.044* | 0.50 |
H21 | 0.5968 | 0.3069 | −0.2390 | 0.050* | 0.50 |
H12 | 0.3365 | 0.0482 | 0.1790 | 0.030* | |
H13 | 0.5880 | 0.1122 | 0.0603 | 0.032* | |
H14 | 0.7041 | 0.3666 | 0.1147 | 0.036* | |
H15 | 0.5255 | 0.4639 | 0.2682 | 0.034* | |
H22 | 0.3277 | 0.4465 | −0.0317 | 0.031* | |
H23 | 0.0723 | 0.3873 | 0.0864 | 0.038* | |
H24 | −0.0654 | 0.1334 | 0.0225 | 0.040* | |
H25 | 0.0968 | 0.0313 | −0.1392 | 0.035* | |
H1 | 0.0252 | 0.1963 | 0.4581 | 0.028* | 0.50 |
H2 | −0.3423 | 0.2958 | 0.7105 | 0.029* | 0.50 |
H31A | 0.0003 | 0.0928 | 0.6115 | 0.030* | |
H31B | −0.1884 | 0.0218 | 0.4980 | 0.030* | |
H32A | −0.3624 | 0.0714 | 0.6323 | 0.035* | |
H32B | −0.1726 | 0.1502 | 0.7441 | 0.035* | |
H41A | −0.2942 | 0.1495 | 0.3686 | 0.034* | |
H41B | −0.1846 | 0.3083 | 0.4032 | 0.034* | |
H42A | −0.3774 | 0.3523 | 0.5266 | 0.033* | |
H42B | −0.4816 | 0.1933 | 0.4962 | 0.033* | |
H51A | 0.1012 | 0.4191 | 0.5788 | 0.033* | |
H51B | 0.1679 | 0.3341 | 0.6647 | 0.033* | |
H52A | −0.0172 | 0.3929 | 0.7885 | 0.034* | |
H52B | −0.0939 | 0.4697 | 0.6977 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0216 (3) | 0.0279 (3) | 0.0201 (2) | 0.00585 (19) | 0.00421 (17) | 0.00887 (18) |
O11 | 0.0321 (13) | 0.0293 (12) | 0.0292 (12) | 0.0095 (10) | 0.0156 (10) | 0.0104 (9) |
O12 | 0.0606 (17) | 0.0307 (13) | 0.0414 (13) | 0.0239 (12) | 0.0295 (12) | 0.0162 (10) |
O21 | 0.0377 (14) | 0.0322 (13) | 0.0365 (13) | 0.0136 (11) | 0.0213 (11) | 0.0123 (10) |
O22 | 0.0378 (15) | 0.0381 (14) | 0.0391 (13) | 0.0034 (11) | 0.0144 (11) | −0.0061 (11) |
C11 | 0.0192 (16) | 0.0279 (16) | 0.0199 (14) | 0.0047 (13) | 0.0022 (12) | 0.0088 (12) |
C12 | 0.0261 (17) | 0.0245 (16) | 0.0252 (16) | 0.0073 (14) | 0.0036 (13) | 0.0102 (13) |
C13 | 0.0229 (17) | 0.0350 (18) | 0.0241 (15) | 0.0102 (14) | 0.0082 (13) | 0.0087 (13) |
C14 | 0.0233 (17) | 0.0388 (19) | 0.0291 (16) | 0.0063 (15) | 0.0052 (13) | 0.0165 (14) |
C15 | 0.0257 (17) | 0.0269 (17) | 0.0276 (16) | 0.0035 (14) | 0.0008 (13) | 0.0087 (13) |
C21 | 0.0240 (17) | 0.0288 (17) | 0.0210 (14) | 0.0108 (14) | 0.0033 (13) | 0.0065 (13) |
C22 | 0.0253 (17) | 0.0290 (17) | 0.0241 (15) | 0.0090 (14) | 0.0011 (13) | 0.0104 (13) |
C23 | 0.0274 (18) | 0.046 (2) | 0.0239 (16) | 0.0179 (16) | 0.0073 (14) | 0.0092 (14) |
C24 | 0.0234 (17) | 0.048 (2) | 0.0275 (16) | 0.0073 (15) | 0.0072 (14) | 0.0141 (15) |
C25 | 0.0284 (18) | 0.0313 (17) | 0.0248 (16) | 0.0057 (15) | 0.0014 (14) | 0.0090 (13) |
C16 | 0.0274 (18) | 0.0316 (18) | 0.0199 (15) | 0.0070 (15) | 0.0009 (13) | 0.0106 (13) |
C26 | 0.0254 (18) | 0.0323 (18) | 0.0216 (15) | 0.0100 (15) | 0.0044 (13) | 0.0087 (14) |
N1 | 0.0251 (14) | 0.0252 (13) | 0.0202 (12) | 0.0081 (11) | 0.0072 (11) | 0.0068 (10) |
N2 | 0.0277 (15) | 0.0266 (14) | 0.0242 (13) | 0.0133 (12) | 0.0104 (11) | 0.0107 (11) |
C31 | 0.0236 (17) | 0.0240 (16) | 0.0282 (16) | 0.0078 (13) | 0.0072 (13) | 0.0087 (13) |
C32 | 0.0360 (19) | 0.0273 (17) | 0.0332 (17) | 0.0140 (15) | 0.0148 (15) | 0.0180 (14) |
C41 | 0.0298 (18) | 0.0367 (18) | 0.0222 (15) | 0.0135 (15) | 0.0050 (13) | 0.0121 (14) |
C42 | 0.0261 (17) | 0.0313 (17) | 0.0259 (16) | 0.0112 (14) | 0.0021 (13) | 0.0104 (13) |
C51 | 0.0263 (17) | 0.0249 (16) | 0.0301 (16) | 0.0060 (14) | 0.0062 (14) | 0.0071 (13) |
C52 | 0.0312 (18) | 0.0287 (17) | 0.0213 (15) | 0.0110 (14) | 0.0020 (13) | 0.0041 (13) |
Fe1—C11 | 2.036 (3) | C22—H22 | 0.95 |
Fe1—C12 | 2.062 (3) | C23—C24 | 1.409 (5) |
Fe1—C13 | 2.061 (3) | C23—H23 | 0.95 |
Fe1—C14 | 2.046 (3) | C24—C25 | 1.415 (4) |
Fe1—C15 | 2.036 (3) | C24—H24 | 0.95 |
Fe1—C21 | 2.043 (3) | C25—H25 | 0.95 |
Fe1—C22 | 2.030 (3) | N1—C31 | 1.483 (4) |
Fe1—C23 | 2.038 (3) | N1—C41 | 1.483 (4) |
Fe1—C24 | 2.053 (3) | N1—C51 | 1.486 (4) |
Fe1—C25 | 2.066 (3) | N1—H1 | 0.93 |
O11—C16 | 1.301 (4) | N2—C52 | 1.481 (4) |
O11—H11 | 0.84 | N2—C42 | 1.489 (4) |
O12—C16 | 1.228 (3) | N2—C32 | 1.489 (3) |
O21—C26 | 1.288 (4) | N2—H2 | 0.93 |
O21—H21 | 0.84 | C31—C32 | 1.535 (4) |
O22—C26 | 1.235 (3) | C31—H31A | 0.99 |
C11—C15 | 1.423 (4) | C31—H31B | 0.99 |
C11—C12 | 1.439 (4) | C32—H32A | 0.99 |
C11—C16 | 1.491 (4) | C32—H32B | 0.99 |
C12—C13 | 1.415 (4) | C41—C42 | 1.545 (4) |
C12—H12 | 0.95 | C41—H41A | 0.99 |
C13—C14 | 1.414 (4) | C41—H41B | 0.99 |
C13—H13 | 0.95 | C42—H42A | 0.99 |
C14—C15 | 1.420 (4) | C42—H42B | 0.99 |
C14—H14 | 0.95 | C51—C52 | 1.542 (4) |
C15—H15 | 0.95 | C51—H51A | 0.99 |
C21—C25 | 1.423 (4) | C51—H51B | 0.99 |
C21—C22 | 1.434 (4) | C52—H52A | 0.99 |
C21—C26 | 1.490 (4) | C52—H52B | 0.99 |
C22—C23 | 1.419 (4) | ||
C16—O11—H11 | 109.5 | C51—N1—H1 | 109.6 |
C26—O21—H21 | 109.5 | C52—N2—C42 | 109.0 (2) |
C15—C11—C12 | 107.9 (3) | C52—N2—C32 | 109.4 (2) |
C15—C11—C16 | 124.4 (3) | C42—N2—C32 | 109.9 (2) |
C12—C11—C16 | 127.7 (3) | C52—N2—H2 | 109.5 |
C13—C12—C11 | 107.4 (3) | C42—N2—H2 | 109.5 |
C13—C12—H12 | 126.3 | C32—N2—H2 | 109.5 |
C11—C12—H12 | 126.3 | N1—C31—C32 | 110.0 (2) |
C14—C13—C12 | 108.6 (2) | N1—C31—H31A | 109.7 |
C14—C13—H13 | 125.7 | C32—C31—H31A | 109.7 |
C12—C13—H13 | 125.7 | N1—C31—H31B | 109.7 |
C13—C14—C15 | 108.4 (3) | C32—C31—H31B | 109.7 |
C13—C14—H14 | 125.8 | H31A—C31—H31B | 108.2 |
C15—C14—H14 | 125.8 | N2—C32—C31 | 109.3 (2) |
C14—C15—C11 | 107.7 (3) | N2—C32—H32A | 109.8 |
C14—C15—H15 | 126.2 | C31—C32—H32A | 109.8 |
C11—C15—H15 | 126.2 | N2—C32—H32B | 109.8 |
C25—C21—C22 | 107.9 (3) | C31—C32—H32B | 109.8 |
C25—C21—C26 | 125.4 (3) | H32A—C32—H32B | 108.3 |
C22—C21—C26 | 126.7 (3) | N1—C41—C42 | 109.6 (2) |
C23—C22—C21 | 107.2 (3) | N1—C41—H41A | 109.7 |
C23—C22—H22 | 126.4 | C42—C41—H41A | 109.7 |
C21—C22—H22 | 126.4 | N1—C41—H41B | 109.7 |
C24—C23—C22 | 108.6 (3) | H41A—C41—H41B | 108.2 |
C24—C23—H23 | 125.7 | N2—C42—C41 | 109.2 (2) |
C22—C23—H23 | 125.7 | N2—C42—H42A | 109.8 |
C23—C24—C25 | 108.5 (3) | C41—C42—H42A | 109.8 |
C23—C24—H24 | 125.7 | N2—C42—H42B | 109.8 |
C25—C24—H24 | 125.7 | C41—C42—H42B | 109.8 |
C24—C25—C21 | 107.8 (3) | H42A—C42—H42B | 108.3 |
C24—C25—H25 | 126.1 | N1—C51—C52 | 109.4 (2) |
C21—C25—H25 | 126.1 | N1—C51—H51A | 109.8 |
O12—C16—O11 | 124.3 (3) | C52—C51—H51A | 109.8 |
O12—C16—C11 | 120.8 (3) | N1—C51—H51B | 109.8 |
O11—C16—C11 | 114.9 (2) | C52—C51—H51B | 109.8 |
O22—C26—O21 | 124.9 (3) | H51A—C51—H51B | 108.3 |
O22—C26—C21 | 119.2 (3) | N2—C52—C51 | 109.6 (2) |
O21—C26—C21 | 115.8 (3) | N2—C52—H52A | 109.7 |
C31—N1—C41 | 109.3 (2) | C51—C52—H52A | 109.7 |
C31—N1—C51 | 109.2 (2) | N2—C52—H52B | 109.7 |
C41—N1—C51 | 109.6 (2) | C51—C52—H52B | 109.7 |
C31—N1—H1 | 109.6 | H52A—C52—H52B | 108.2 |
C41—N1—H1 | 109.6 | ||
C15—C11—C12—C13 | −0.4 (3) | C22—C21—C26—O22 | −170.6 (3) |
C16—C11—C12—C13 | 178.0 (3) | C25—C21—C26—O21 | −170.4 (3) |
C11—C12—C13—C14 | 0.2 (3) | C22—C21—C26—O21 | 8.2 (4) |
C12—C13—C14—C15 | 0.0 (3) | C41—N1—C31—C32 | −61.9 (3) |
C13—C14—C15—C11 | −0.2 (3) | C51—N1—C31—C32 | 58.0 (3) |
C12—C11—C15—C14 | 0.3 (3) | C52—N2—C32—C31 | −61.7 (3) |
C16—C11—C15—C14 | −178.1 (3) | C42—N2—C32—C31 | 57.9 (3) |
C25—C21—C22—C23 | −0.1 (3) | N1—C31—C32—N2 | 3.2 (3) |
C26—C21—C22—C23 | −178.9 (3) | C31—N1—C41—C42 | 58.6 (3) |
C21—C22—C23—C24 | 0.5 (3) | C51—N1—C41—C42 | −61.1 (3) |
C22—C23—C24—C25 | −0.7 (3) | C52—N2—C42—C41 | 59.0 (3) |
C23—C24—C25—C21 | 0.7 (3) | C32—N2—C42—C41 | −60.9 (3) |
C22—C21—C25—C24 | −0.4 (3) | N1—C41—C42—N2 | 2.1 (3) |
C26—C21—C25—C24 | 178.4 (3) | C31—N1—C51—C52 | −61.8 (3) |
C15—C11—C16—O12 | 7.3 (4) | C41—N1—C51—C52 | 57.9 (3) |
C12—C11—C16—O12 | −170.9 (3) | C42—N2—C52—C51 | −62.3 (3) |
C15—C11—C16—O11 | −171.9 (3) | C32—N2—C52—C51 | 57.9 (3) |
C12—C11—C16—O11 | 9.9 (4) | N1—C51—C52—N2 | 3.4 (3) |
C25—C21—C26—O22 | 10.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N1 | 0.84 | 1.74 | 2.580 (3) | 178 |
N1—H1···O11 | 0.93 | 1.65 | 2.580 (3) | 176 |
O21—H21···N2i | 0.84 | 1.72 | 2.552 (3) | 174 |
N2—H2···O21ii | 0.93 | 1.62 | 2.552 (3) | 177 |
C31—H31B···O22iii | 0.99 | 2.47 | 3.373 (4) | 152 |
C52—H52B···O12iv | 0.99 | 2.33 | 3.262 (4) | 157 |
Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1; (iii) −x, −y, −z; (iv) −x, −y+1, −z+1. |
C12H8FeO4·2(C4H10NO)·H2O | F(000) = 984 |
Mr = 466.31 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3487 reflections |
a = 7.4018 (2) Å | θ = 2.6–27.5° |
b = 9.2018 (3) Å | µ = 0.79 mm−1 |
c = 30.3884 (11) Å | T = 150 K |
β = 101.0630 (15)° | Block, red |
V = 2031.29 (11) Å3 | 0.18 × 0.14 × 0.14 mm |
Z = 4 |
Kappa-CCD diffractometer | 4458 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2882 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→9 |
Tmin = 0.871, Tmax = 0.898 | k = −11→0 |
10444 measured reflections | l = −39→37 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0295P)2 + 0.1109P] where P = (Fo2 + 2Fc2)/3 |
4458 reflections | (Δ/σ)max = 0.001 |
279 parameters | Δρmax = 0.39 e Å−3 |
2 restraints | Δρmin = −0.37 e Å−3 |
C12H8FeO4·2(C4H10NO)·H2O | V = 2031.29 (11) Å3 |
Mr = 466.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4018 (2) Å | µ = 0.79 mm−1 |
b = 9.2018 (3) Å | T = 150 K |
c = 30.3884 (11) Å | 0.18 × 0.14 × 0.14 mm |
β = 101.0630 (15)° |
Kappa-CCD diffractometer | 4458 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2882 reflections with I > 2σ(I) |
Tmin = 0.871, Tmax = 0.898 | Rint = 0.047 |
10444 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 2 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.39 e Å−3 |
4458 reflections | Δρmin = −0.37 e Å−3 |
279 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.42731 (5) | 0.70161 (4) | 0.176443 (12) | 0.01882 (13) | |
O11 | 0.0248 (3) | 0.5202 (2) | 0.09370 (6) | 0.0312 (5) | |
O12 | 0.2350 (3) | 0.5993 (2) | 0.05505 (6) | 0.0341 (5) | |
C11 | 0.2140 (3) | 0.7175 (3) | 0.12270 (9) | 0.0202 (6) | |
C12 | 0.3461 (4) | 0.8298 (3) | 0.12145 (9) | 0.0241 (7) | |
C13 | 0.3614 (4) | 0.9138 (3) | 0.16104 (9) | 0.0259 (7) | |
C14 | 0.2401 (3) | 0.8548 (3) | 0.18693 (9) | 0.0239 (6) | |
C15 | 0.1489 (3) | 0.7341 (3) | 0.16371 (9) | 0.0223 (6) | |
C16 | 0.1555 (4) | 0.6031 (3) | 0.08781 (9) | 0.0264 (7) | |
O21 | 0.3229 (3) | 0.30737 (19) | 0.15252 (7) | 0.0329 (5) | |
O22 | 0.5476 (2) | 0.3492 (2) | 0.11441 (6) | 0.0291 (5) | |
C21 | 0.5347 (3) | 0.4971 (3) | 0.17726 (9) | 0.0190 (6) | |
C22 | 0.6679 (3) | 0.6031 (3) | 0.17008 (9) | 0.0201 (6) | |
C23 | 0.6982 (3) | 0.6982 (3) | 0.20727 (9) | 0.0214 (6) | |
C24 | 0.5863 (3) | 0.6531 (3) | 0.23775 (9) | 0.0225 (6) | |
C25 | 0.4842 (3) | 0.5294 (3) | 0.21933 (9) | 0.0214 (6) | |
C26 | 0.4592 (4) | 0.3758 (3) | 0.14612 (9) | 0.0250 (7) | |
O31 | −0.1271 (3) | 0.03813 (19) | 0.19230 (6) | 0.0309 (5) | |
C32 | −0.1750 (4) | 0.0391 (3) | 0.14437 (9) | 0.0298 (7) | |
C33 | −0.0587 (4) | 0.1465 (3) | 0.12451 (9) | 0.0254 (7) | |
N34 | −0.0829 (3) | 0.2936 (2) | 0.14246 (7) | 0.0225 (5) | |
C35 | −0.0394 (4) | 0.2928 (3) | 0.19249 (9) | 0.0259 (7) | |
C36 | −0.1540 (4) | 0.1780 (3) | 0.20964 (9) | 0.0290 (7) | |
O41 | 0.3349 (3) | 0.1157 (3) | −0.04061 (7) | 0.0464 (6) | |
C42 | 0.3282 (5) | 0.2720 (4) | −0.03898 (11) | 0.0518 (10) | |
C43 | 0.4041 (4) | 0.3271 (3) | 0.00655 (11) | 0.0422 (9) | |
N44 | 0.3103 (3) | 0.2630 (2) | 0.03983 (7) | 0.0278 (6) | |
C45 | 0.3066 (4) | 0.1025 (3) | 0.03686 (10) | 0.0349 (8) | |
C46 | 0.2294 (4) | 0.0577 (4) | −0.01085 (12) | 0.0497 (10) | |
O5 | −0.0697 (3) | 0.3196 (2) | 0.02889 (7) | 0.0316 (5) | |
H12 | 0.4124 | 0.8454 | 0.0980 | 0.029* | |
H13 | 0.4397 | 0.9954 | 0.1688 | 0.031* | |
H14 | 0.2225 | 0.8902 | 0.2152 | 0.029* | |
H15 | 0.0600 | 0.6745 | 0.1737 | 0.027* | |
H22 | 0.7257 | 0.6084 | 0.1448 | 0.024* | |
H23 | 0.7798 | 0.7789 | 0.2112 | 0.026* | |
H24 | 0.5806 | 0.6977 | 0.2656 | 0.027* | |
H25 | 0.3977 | 0.4772 | 0.2326 | 0.026* | |
H32A | −0.3066 | 0.0650 | 0.1350 | 0.036* | |
H32B | −0.1572 | −0.0594 | 0.1328 | 0.036* | |
H33A | 0.0725 | 0.1178 | 0.1322 | 0.030* | |
H33B | −0.0962 | 0.1471 | 0.0914 | 0.030* | |
H34A | −0.2024 | 0.3238 | 0.1328 | 0.027* | |
H34B | −0.0065 | 0.3581 | 0.1318 | 0.027* | |
H35A | −0.0666 | 0.3893 | 0.2041 | 0.031* | |
H35B | 0.0930 | 0.2720 | 0.2031 | 0.031* | |
H36A | −0.1214 | 0.1750 | 0.2428 | 0.035* | |
H36B | −0.2857 | 0.2046 | 0.2012 | 0.035* | |
H42A | 0.1991 | 0.3047 | −0.0481 | 0.062* | |
H42B | 0.3997 | 0.3129 | −0.0605 | 0.062* | |
H43A | 0.5371 | 0.3041 | 0.0143 | 0.051* | |
H43B | 0.3906 | 0.4341 | 0.0070 | 0.051* | |
H44A | 0.1916 | 0.2976 | 0.0355 | 0.033* | |
H44B | 0.3695 | 0.2904 | 0.0680 | 0.033* | |
H45A | 0.2292 | 0.0626 | 0.0572 | 0.042* | |
H45B | 0.4328 | 0.0635 | 0.0462 | 0.042* | |
H46A | 0.2286 | −0.0497 | −0.0130 | 0.060* | |
H46B | 0.1008 | 0.0923 | −0.0194 | 0.060* | |
H51 | −0.049 (4) | 0.398 (3) | 0.0446 (9) | 0.038 (6)* | |
H52 | −0.128 (4) | 0.346 (3) | 0.0032 (8) | 0.038 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0177 (2) | 0.0177 (2) | 0.0210 (2) | 0.00055 (17) | 0.00330 (17) | 0.00050 (18) |
O11 | 0.0350 (12) | 0.0283 (11) | 0.0283 (12) | −0.0081 (9) | 0.0008 (10) | 0.0003 (9) |
O12 | 0.0323 (12) | 0.0477 (14) | 0.0220 (11) | 0.0012 (10) | 0.0041 (10) | −0.0052 (10) |
C11 | 0.0164 (14) | 0.0224 (15) | 0.0207 (15) | 0.0024 (12) | 0.0004 (12) | 0.0031 (12) |
C12 | 0.0254 (15) | 0.0229 (16) | 0.0243 (16) | 0.0041 (12) | 0.0057 (13) | 0.0070 (13) |
C13 | 0.0272 (16) | 0.0152 (15) | 0.0360 (18) | −0.0014 (12) | 0.0081 (14) | 0.0008 (13) |
C14 | 0.0234 (15) | 0.0224 (15) | 0.0263 (16) | 0.0054 (12) | 0.0056 (14) | −0.0023 (13) |
C15 | 0.0145 (14) | 0.0227 (15) | 0.0296 (17) | 0.0008 (12) | 0.0038 (13) | 0.0034 (13) |
C16 | 0.0236 (16) | 0.0289 (17) | 0.0234 (17) | 0.0070 (14) | −0.0036 (14) | 0.0029 (14) |
O21 | 0.0292 (11) | 0.0246 (11) | 0.0453 (13) | −0.0097 (9) | 0.0077 (10) | −0.0048 (10) |
O22 | 0.0233 (10) | 0.0340 (11) | 0.0291 (12) | 0.0031 (9) | 0.0027 (9) | −0.0123 (9) |
C21 | 0.0156 (14) | 0.0175 (14) | 0.0227 (15) | 0.0022 (11) | 0.0006 (12) | −0.0003 (12) |
C22 | 0.0153 (13) | 0.0227 (15) | 0.0222 (15) | 0.0022 (12) | 0.0035 (12) | −0.0001 (12) |
C23 | 0.0154 (14) | 0.0197 (14) | 0.0283 (16) | −0.0025 (12) | 0.0024 (12) | −0.0015 (13) |
C24 | 0.0259 (16) | 0.0203 (15) | 0.0186 (15) | 0.0012 (12) | −0.0025 (13) | 0.0001 (12) |
C25 | 0.0201 (15) | 0.0199 (15) | 0.0238 (16) | 0.0035 (12) | 0.0036 (13) | 0.0054 (12) |
C26 | 0.0222 (15) | 0.0208 (16) | 0.0280 (17) | 0.0061 (13) | −0.0049 (14) | 0.0019 (13) |
O31 | 0.0419 (12) | 0.0251 (11) | 0.0267 (12) | 0.0036 (9) | 0.0090 (10) | 0.0040 (9) |
C32 | 0.0319 (17) | 0.0265 (16) | 0.0303 (18) | −0.0008 (14) | 0.0045 (14) | −0.0026 (14) |
C33 | 0.0274 (16) | 0.0257 (15) | 0.0235 (16) | 0.0043 (13) | 0.0059 (13) | 0.0004 (13) |
N34 | 0.0174 (12) | 0.0235 (13) | 0.0262 (14) | −0.0018 (10) | 0.0035 (10) | 0.0041 (11) |
C35 | 0.0254 (16) | 0.0272 (16) | 0.0242 (16) | 0.0030 (13) | 0.0024 (13) | −0.0022 (13) |
C36 | 0.0328 (17) | 0.0304 (18) | 0.0259 (17) | 0.0036 (14) | 0.0109 (14) | 0.0011 (13) |
O41 | 0.0445 (14) | 0.0612 (16) | 0.0342 (13) | 0.0135 (12) | 0.0093 (11) | −0.0138 (12) |
C42 | 0.056 (2) | 0.063 (3) | 0.041 (2) | 0.035 (2) | 0.0210 (19) | 0.0170 (19) |
C43 | 0.043 (2) | 0.0301 (19) | 0.061 (2) | −0.0024 (15) | 0.0278 (19) | 0.0041 (17) |
N44 | 0.0240 (13) | 0.0340 (14) | 0.0237 (14) | 0.0045 (11) | 0.0006 (11) | −0.0042 (11) |
C45 | 0.0429 (19) | 0.0266 (17) | 0.039 (2) | 0.0064 (15) | 0.0169 (16) | 0.0087 (15) |
C46 | 0.041 (2) | 0.039 (2) | 0.069 (3) | −0.0100 (16) | 0.012 (2) | −0.0268 (19) |
O5 | 0.0329 (13) | 0.0318 (13) | 0.0279 (13) | 0.0033 (10) | 0.0005 (11) | −0.0011 (10) |
Fe1—C12 | 2.039 (3) | O31—C36 | 1.419 (3) |
Fe1—C22 | 2.041 (2) | O31—C32 | 1.432 (3) |
Fe1—C21 | 2.041 (2) | C32—C33 | 1.511 (3) |
Fe1—C25 | 2.044 (3) | C32—H32A | 0.99 |
Fe1—C15 | 2.044 (2) | C32—H32B | 0.99 |
Fe1—C23 | 2.044 (3) | C33—N34 | 1.483 (3) |
Fe1—C14 | 2.044 (2) | C33—H33A | 0.99 |
Fe1—C13 | 2.044 (3) | C33—H33B | 0.99 |
Fe1—C11 | 2.048 (3) | N34—C35 | 1.492 (3) |
Fe1—C24 | 2.053 (3) | N34—H34A | 0.92 |
O11—C16 | 1.271 (3) | N34—H34B | 0.92 |
O12—C16 | 1.250 (3) | C35—C36 | 1.508 (3) |
C11—C15 | 1.428 (3) | C35—H35A | 0.99 |
C11—C12 | 1.428 (3) | C35—H35B | 0.99 |
C11—C16 | 1.498 (4) | C36—H36A | 0.99 |
C12—C13 | 1.416 (4) | C36—H36B | 0.99 |
C12—H12 | 0.95 | O41—C46 | 1.409 (3) |
C13—C14 | 1.411 (3) | O41—C42 | 1.440 (4) |
C13—H13 | 0.95 | C42—C43 | 1.480 (5) |
C14—C15 | 1.415 (4) | C42—H42A | 0.99 |
C14—H14 | 0.95 | C42—H42B | 0.99 |
C15—H15 | 0.95 | C43—N44 | 1.457 (3) |
O21—C26 | 1.236 (3) | C43—H43A | 0.99 |
O22—C26 | 1.288 (3) | C43—H43B | 0.99 |
C21—C25 | 1.430 (3) | N44—C45 | 1.479 (3) |
C21—C22 | 1.433 (3) | N44—H44A | 0.92 |
C21—C26 | 1.500 (4) | N44—H44B | 0.92 |
C22—C23 | 1.413 (3) | C45—C46 | 1.510 (4) |
C22—H22 | 0.95 | C45—H45A | 0.99 |
C23—C24 | 1.418 (3) | C45—H45B | 0.99 |
C23—H23 | 0.95 | C46—H46A | 0.99 |
C24—C25 | 1.420 (3) | C46—H46B | 0.99 |
C24—H24 | 0.95 | O5—H51 | 0.86 (2) |
C25—H25 | 0.95 | O5—H52 | 0.85 (2) |
C15—C11—C12 | 107.0 (2) | C33—N34—H34A | 109.5 |
C15—C11—C16 | 126.4 (2) | C35—N34—H34A | 109.5 |
C12—C11—C16 | 126.6 (2) | C33—N34—H34B | 109.5 |
C13—C12—C11 | 108.4 (2) | C35—N34—H34B | 109.5 |
C13—C12—H12 | 125.8 | H34A—N34—H34B | 108.1 |
C11—C12—H12 | 125.8 | N34—C35—C36 | 109.3 (2) |
C14—C13—C12 | 107.9 (2) | N34—C35—H35A | 109.8 |
C14—C13—H13 | 126.0 | C36—C35—H35A | 109.8 |
C12—C13—H13 | 126.0 | N34—C35—H35B | 109.8 |
C13—C14—C15 | 108.5 (2) | C36—C35—H35B | 109.8 |
C13—C14—H14 | 125.8 | H35A—C35—H35B | 108.3 |
C15—C14—H14 | 125.8 | O31—C36—C35 | 112.3 (2) |
C14—C15—C11 | 108.1 (2) | O31—C36—H36A | 109.2 |
C14—C15—H15 | 125.9 | C35—C36—H36A | 109.2 |
C11—C15—H15 | 125.9 | O31—C36—H36B | 109.2 |
O12—C16—O11 | 125.6 (3) | C35—C36—H36B | 109.2 |
O12—C16—C11 | 117.8 (2) | H36A—C36—H36B | 107.9 |
O11—C16—C11 | 116.5 (2) | C46—O41—C42 | 109.3 (2) |
C25—C21—C22 | 107.5 (2) | O41—C42—C43 | 111.4 (3) |
C25—C21—C26 | 126.1 (2) | O41—C42—H42A | 109.3 |
C22—C21—C26 | 126.4 (2) | C43—C42—H42A | 109.3 |
C23—C22—C21 | 107.9 (2) | O41—C42—H42B | 109.3 |
C23—C22—H22 | 126.0 | C43—C42—H42B | 109.3 |
C21—C22—H22 | 126.0 | H42A—C42—H42B | 108.0 |
C22—C23—C24 | 108.5 (2) | N44—C43—C42 | 111.4 (3) |
C22—C23—H23 | 125.7 | N44—C43—H43A | 109.4 |
C24—C23—H23 | 125.7 | C42—C43—H43A | 109.4 |
C23—C24—C25 | 108.1 (2) | N44—C43—H43B | 109.4 |
C23—C24—H24 | 125.9 | C42—C43—H43B | 109.4 |
C25—C24—H24 | 125.9 | H43A—C43—H43B | 108.0 |
C24—C25—C21 | 107.9 (2) | C43—N44—C45 | 111.6 (2) |
C24—C25—H25 | 126.0 | C43—N44—H44A | 109.3 |
C21—C25—H25 | 126.0 | C45—N44—H44A | 109.3 |
O21—C26—O22 | 124.6 (3) | C43—N44—H44B | 109.3 |
O21—C26—C21 | 119.8 (2) | C45—N44—H44B | 109.3 |
O22—C26—C21 | 115.6 (2) | H44A—N44—H44B | 108.0 |
C36—O31—C32 | 110.3 (2) | N44—C45—C46 | 109.3 (2) |
O31—C32—C33 | 111.2 (2) | N44—C45—H45A | 109.8 |
O31—C32—H32A | 109.4 | C46—C45—H45A | 109.8 |
C33—C32—H32A | 109.4 | N44—C45—H45B | 109.8 |
O31—C32—H32B | 109.4 | C46—C45—H45B | 109.8 |
C33—C32—H32B | 109.4 | H45A—C45—H45B | 108.3 |
H32A—C32—H32B | 108.0 | O41—C46—C45 | 111.0 (2) |
N34—C33—C32 | 109.4 (2) | O41—C46—H46A | 109.4 |
N34—C33—H33A | 109.8 | C45—C46—H46A | 109.4 |
C32—C33—H33A | 109.8 | O41—C46—H46B | 109.4 |
N34—C33—H33B | 109.8 | C45—C46—H46B | 109.4 |
C32—C33—H33B | 109.8 | H46A—C46—H46B | 108.0 |
H33A—C33—H33B | 108.2 | H51—O5—H52 | 106 (3) |
C33—N34—C35 | 110.6 (2) | ||
C15—C11—C12—C13 | −0.1 (3) | C26—C21—C25—C24 | −179.5 (2) |
C16—C11—C12—C13 | −179.6 (2) | C25—C21—C26—O21 | 11.3 (4) |
C11—C12—C13—C14 | 0.0 (3) | C22—C21—C26—O21 | −167.7 (2) |
C12—C13—C14—C15 | 0.1 (3) | C25—C21—C26—O22 | −167.3 (2) |
C13—C14—C15—C11 | −0.1 (3) | C22—C21—C26—O22 | 13.7 (4) |
C12—C11—C15—C14 | 0.1 (3) | C36—O31—C32—C33 | 59.8 (3) |
C16—C11—C15—C14 | 179.7 (2) | O31—C32—C33—N34 | −58.1 (3) |
C15—C11—C16—O12 | −175.8 (2) | C32—C33—N34—C35 | 55.6 (3) |
C12—C11—C16—O12 | 3.7 (4) | C33—N34—C35—C36 | −54.5 (3) |
C15—C11—C16—O11 | 6.0 (4) | C32—O31—C36—C35 | −59.4 (3) |
C12—C11—C16—O11 | −174.5 (2) | N34—C35—C36—O31 | 56.6 (3) |
C25—C21—C22—C23 | 0.1 (3) | C46—O41—C42—C43 | 60.5 (3) |
C26—C21—C22—C23 | 179.2 (2) | O41—C42—C43—N44 | −55.6 (3) |
C21—C22—C23—C24 | 0.2 (3) | C42—C43—N44—C45 | 52.0 (3) |
C22—C23—C24—C25 | −0.4 (3) | C43—N44—C45—C46 | −52.5 (3) |
C23—C24—C25—C21 | 0.5 (3) | C42—O41—C46—C45 | −61.9 (3) |
C22—C21—C25—C24 | −0.3 (3) | N44—C45—C46—O41 | 58.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N34—H34A···O22i | 0.92 | 1.84 | 2.752 (3) | 170 |
N34—H34B···O11 | 0.92 | 1.93 | 2.763 (3) | 150 |
N44—H44A···O5 | 0.92 | 1.92 | 2.817 (3) | 166 |
N44—H44B···O22 | 0.92 | 1.82 | 2.706 (3) | 162 |
O5—H51···O11 | 0.86 (2) | 1.86 (2) | 2.692 (3) | 160 (3) |
O5—H52···O12ii | 0.85 (2) | 1.86 (2) | 2.715 (3) | 175 (3) |
C45—H45B···O41iii | 0.95 | 2.41 | 3.312 (4) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z. |
C12H10FeO4·C10H8N2 | Z = 2 |
Mr = 430.23 | F(000) = 444 |
Triclinic, P1 | Dx = 1.584 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9500 (2) Å | Cell parameters from 3636 reflections |
b = 10.7645 (3) Å | θ = 3.0–27.5° |
c = 12.5260 (4) Å | µ = 0.87 mm−1 |
α = 97.8780 (11)° | T = 150 K |
β = 92.0960 (11)° | Needle, colourless |
γ = 102.9980 (13)° | 0.24 × 0.13 × 0.11 mm |
V = 902.27 (5) Å3 |
Kappa-CCD diffractometer | 4096 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3141 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→9 |
Tmin = 0.818, Tmax = 0.910 | k = −13→13 |
10111 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2)P)2 + 0.5387P] where P = (Fo2 + 2Fc2)/3 |
4096 reflections | (Δ/σ)max < 0.001 |
264 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C12H10FeO4·C10H8N2 | γ = 102.9980 (13)° |
Mr = 430.23 | V = 902.27 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9500 (2) Å | Mo Kα radiation |
b = 10.7645 (3) Å | µ = 0.87 mm−1 |
c = 12.5260 (4) Å | T = 150 K |
α = 97.8780 (11)° | 0.24 × 0.13 × 0.11 mm |
β = 92.0960 (11)° |
Kappa-CCD diffractometer | 4096 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 3141 reflections with I > 2σ(I) |
Tmin = 0.818, Tmax = 0.910 | Rint = 0.039 |
10111 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.52 e Å−3 |
4096 reflections | Δρmin = −0.32 e Å−3 |
264 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.2653 (0.0069) x - 3.5191 (0.0109) y + 10.7675 (0.0072) z = 4.3998 (0.0034) * -0.0002 (0.0005) C11 * 0.0008 (0.0018) C16 * -0.0003 (0.0006) O11 * -0.0003 (0.0007) O12 Rms deviation of fitted atoms = 0.0005 3.5493 (0.0040) x - 3.4626 (0.0111) y + 10.4749 (0.0046) z = 4.4266 (0.0036) Angle to previous plane (with approximate e.s.d.) = 2.74 (0.12) * -0.0343 (0.0018) C11 * -0.0182 (0.0014) C12 * 0.0195 (0.0015) C13 * 0.0169 (0.0015) C14 * -0.0176 (0.0015) C15 * 0.0336 (0.0012) C16 Rms deviation of fitted atoms = 0.0245 3.7346 (0.0040) x - 3.3918 (0.0108) y + 10.2690 (0.0048) z = 7.6945 (0.0037) Angle to previous plane (with approximate e.s.d.) = 1.87 (0.10) * 0.0001 (0.0018) C21 * -0.0042 (0.0014) C22 * 0.0043 (0.0014) C23 * -0.0011 (0.0015) C24 * -0.0010 (0.0015) C25 * 0.0019 (0.0011) C26 Rms deviation of fitted atoms = 0.0027 3.5968 (0.0066) x - 4.8169 (0.0102) y + 10.1178 (0.0081) z = 7.1948 (0.0072) Angle to previous plane (with approximate e.s.d.) = 8.37 (0.13) * 0.0023 (0.0005) C21 * -0.0080 (0.0017) C26 * 0.0026 (0.0006) O21 * 0.0031 (0.0007) O22 Rms deviation of fitted atoms = 0.0046 ######################################################################## 3.8270 (0.0031) x - 2.2163 (0.0092) y + 10.1842 (0.0040) z = 5.1846 (0.0042) * -0.0047 (0.0015) N31 * -0.0013 (0.0015) C32 * 0.0063 (0.0016) C33 * -0.0019 (0.0018) C34 * 0.0036 (0.0016) C35 * 0.0016 (0.0015) C36 * -0.0036 (0.0012) C44 Rms deviation of fitted atoms = 0.0037 3.0262 (0.0037) x - 6.6685 (0.0074) y + 9.7591 (0.0049) z = 2.9563 (0.0066) Angle to previous plane (with approximate e.s.d.) = 27.63 (0.07) * 0.0001 (0.0015) N41 * -0.0017 (0.0016) C42 * 0.0019 (0.0016) C43 * 0.0003 (0.0017) C44 * -0.0002 (0.0016) C45 * 0.0005 (0.0015) C46 * -0.0008 (0.0012) C34 Rms deviation of fitted atoms = 0.0010 |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.31696 (4) | 0.24252 (3) | 0.55276 (2) | 0.01873 (10) | |
O11 | 0.6320 (2) | 0.35237 (14) | 0.33209 (14) | 0.0275 (4) | |
O12 | 0.5330 (2) | 0.13754 (15) | 0.29189 (14) | 0.0312 (4) | |
C11 | 0.3279 (3) | 0.2510 (2) | 0.39120 (17) | 0.0192 (4) | |
C12 | 0.2826 (3) | 0.3657 (2) | 0.44600 (18) | 0.0209 (5) | |
C13 | 0.1047 (3) | 0.3289 (2) | 0.49770 (19) | 0.0260 (5) | |
C14 | 0.0387 (3) | 0.1920 (2) | 0.47458 (19) | 0.0268 (5) | |
C15 | 0.1745 (3) | 0.1438 (2) | 0.40932 (18) | 0.0242 (5) | |
C16 | 0.5063 (3) | 0.2405 (2) | 0.33376 (17) | 0.0208 (5) | |
O21 | 0.0087 (2) | 0.15354 (15) | 0.78138 (14) | 0.0292 (4) | |
O22 | 0.1424 (2) | 0.36437 (15) | 0.83426 (14) | 0.0306 (4) | |
C21 | 0.3123 (3) | 0.2429 (2) | 0.71594 (17) | 0.0190 (4) | |
C22 | 0.3467 (3) | 0.1235 (2) | 0.66359 (18) | 0.0213 (5) | |
C23 | 0.5231 (3) | 0.1524 (2) | 0.60982 (18) | 0.0235 (5) | |
C24 | 0.5975 (3) | 0.2883 (2) | 0.62711 (19) | 0.0258 (5) | |
C25 | 0.4686 (3) | 0.3442 (2) | 0.69248 (18) | 0.0226 (5) | |
C26 | 0.1470 (3) | 0.2604 (2) | 0.78200 (18) | 0.0219 (5) | |
N31 | 0.9423 (3) | 0.31428 (18) | 0.22291 (15) | 0.0232 (4) | |
C32 | 0.9606 (3) | 0.1937 (2) | 0.19010 (18) | 0.0244 (5) | |
C33 | 1.1110 (3) | 0.1660 (2) | 0.12832 (18) | 0.0231 (5) | |
C34 | 1.2512 (3) | 0.2660 (2) | 0.09661 (17) | 0.0188 (4) | |
C35 | 1.2322 (3) | 0.3914 (2) | 0.13157 (18) | 0.0227 (5) | |
C36 | 1.0784 (3) | 0.4108 (2) | 0.19338 (18) | 0.0240 (5) | |
N41 | 1.7214 (3) | 0.19475 (18) | −0.09777 (15) | 0.0240 (4) | |
C42 | 1.7425 (3) | 0.3055 (2) | −0.02883 (19) | 0.0248 (5) | |
C43 | 1.5958 (3) | 0.3322 (2) | 0.03527 (18) | 0.0232 (5) | |
C44 | 1.4148 (3) | 0.2423 (2) | 0.02979 (17) | 0.0190 (4) | |
C45 | 1.3938 (3) | 0.1278 (2) | −0.04199 (18) | 0.0226 (5) | |
C46 | 1.5487 (3) | 0.1086 (2) | −0.10305 (18) | 0.0236 (5) | |
H11 | 0.7304 | 0.3401 | 0.2988 | 0.041* | |
H12 | 0.3583 | 0.4513 | 0.4475 | 0.025* | |
H13 | 0.0408 | 0.3855 | 0.5403 | 0.031* | |
H14 | −0.0773 | 0.1418 | 0.4990 | 0.032* | |
H15 | 0.1659 | 0.0557 | 0.3822 | 0.029* | |
H21 | −0.0812 | 0.1694 | 0.8204 | 0.044* | |
H22 | 0.2655 | 0.0400 | 0.6648 | 0.026* | |
H23 | 0.5818 | 0.0914 | 0.5691 | 0.028* | |
H24 | 0.7139 | 0.3337 | 0.5995 | 0.031* | |
H25 | 0.4834 | 0.4337 | 0.7166 | 0.027* | |
H32 | 0.8659 | 0.1239 | 0.2103 | 0.029* | |
H33 | 1.1186 | 0.0791 | 0.1076 | 0.028* | |
H35 | 1.3249 | 0.4631 | 0.1128 | 0.027* | |
H36 | 1.0683 | 0.4968 | 0.2162 | 0.029* | |
H42 | 1.8643 | 0.3680 | −0.0243 | 0.030* | |
H43 | 1.6176 | 0.4114 | 0.0830 | 0.028* | |
H45 | 1.2736 | 0.0636 | −0.0487 | 0.027* | |
H46 | 1.5316 | 0.0302 | −0.1513 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01734 (16) | 0.02063 (17) | 0.01844 (17) | 0.00387 (12) | 0.00389 (12) | 0.00388 (12) |
O11 | 0.0237 (8) | 0.0247 (8) | 0.0348 (10) | 0.0044 (7) | 0.0160 (7) | 0.0046 (7) |
O12 | 0.0339 (9) | 0.0237 (8) | 0.0357 (10) | 0.0083 (7) | 0.0122 (8) | −0.0025 (7) |
C11 | 0.0177 (10) | 0.0235 (11) | 0.0163 (11) | 0.0037 (9) | 0.0015 (9) | 0.0040 (9) |
C12 | 0.0209 (11) | 0.0220 (11) | 0.0213 (11) | 0.0065 (9) | 0.0032 (9) | 0.0051 (9) |
C13 | 0.0213 (11) | 0.0329 (13) | 0.0275 (13) | 0.0121 (10) | 0.0048 (10) | 0.0064 (11) |
C14 | 0.0154 (11) | 0.0365 (13) | 0.0274 (13) | 0.0002 (10) | 0.0021 (9) | 0.0106 (11) |
C15 | 0.0252 (12) | 0.0224 (11) | 0.0214 (12) | −0.0008 (9) | −0.0019 (9) | 0.0022 (9) |
C16 | 0.0235 (11) | 0.0226 (11) | 0.0172 (11) | 0.0053 (9) | 0.0032 (9) | 0.0055 (9) |
O21 | 0.0239 (9) | 0.0279 (9) | 0.0346 (10) | 0.0030 (7) | 0.0144 (7) | 0.0026 (7) |
O22 | 0.0337 (9) | 0.0258 (9) | 0.0332 (10) | 0.0100 (7) | 0.0123 (8) | 0.0001 (7) |
C21 | 0.0201 (11) | 0.0221 (11) | 0.0152 (10) | 0.0055 (9) | 0.0019 (9) | 0.0030 (9) |
C22 | 0.0234 (11) | 0.0197 (11) | 0.0224 (11) | 0.0073 (9) | 0.0026 (9) | 0.0042 (9) |
C23 | 0.0220 (11) | 0.0283 (12) | 0.0230 (12) | 0.0122 (10) | 0.0045 (9) | 0.0021 (10) |
C24 | 0.0168 (11) | 0.0324 (13) | 0.0279 (13) | 0.0028 (10) | 0.0027 (9) | 0.0081 (10) |
C25 | 0.0242 (11) | 0.0197 (11) | 0.0216 (12) | 0.0019 (9) | −0.0006 (9) | 0.0011 (9) |
C26 | 0.0239 (12) | 0.0260 (12) | 0.0181 (11) | 0.0084 (10) | 0.0033 (9) | 0.0061 (9) |
N31 | 0.0205 (10) | 0.0309 (10) | 0.0196 (10) | 0.0081 (8) | 0.0041 (8) | 0.0045 (8) |
C32 | 0.0233 (12) | 0.0273 (12) | 0.0226 (12) | 0.0035 (10) | 0.0034 (9) | 0.0071 (10) |
C33 | 0.0233 (11) | 0.0224 (11) | 0.0245 (12) | 0.0064 (9) | 0.0036 (9) | 0.0050 (9) |
C34 | 0.0177 (10) | 0.0233 (11) | 0.0156 (10) | 0.0050 (9) | 0.0006 (8) | 0.0036 (9) |
C35 | 0.0213 (11) | 0.0240 (11) | 0.0222 (11) | 0.0036 (9) | 0.0038 (9) | 0.0036 (9) |
C36 | 0.0245 (12) | 0.0241 (11) | 0.0239 (12) | 0.0081 (10) | 0.0036 (10) | 0.0005 (10) |
N41 | 0.0217 (10) | 0.0310 (10) | 0.0213 (10) | 0.0088 (8) | 0.0038 (8) | 0.0057 (8) |
C42 | 0.0195 (11) | 0.0276 (12) | 0.0257 (12) | 0.0019 (9) | 0.0024 (9) | 0.0045 (10) |
C43 | 0.0216 (11) | 0.0253 (11) | 0.0224 (12) | 0.0056 (9) | 0.0021 (9) | 0.0021 (9) |
C44 | 0.0192 (11) | 0.0240 (11) | 0.0156 (10) | 0.0072 (9) | 0.0011 (9) | 0.0053 (9) |
C45 | 0.0206 (11) | 0.0232 (11) | 0.0224 (12) | 0.0028 (9) | 0.0010 (9) | 0.0017 (9) |
C46 | 0.0258 (12) | 0.0256 (12) | 0.0198 (11) | 0.0077 (10) | 0.0031 (9) | 0.0021 (9) |
Fe1—C11 | 2.042 (2) | C22—C23 | 1.414 (3) |
Fe1—C12 | 2.052 (2) | C22—H22 | 0.95 |
Fe1—C13 | 2.058 (2) | C23—C24 | 1.421 (3) |
Fe1—C14 | 2.059 (2) | C23—H23 | 0.95 |
Fe1—C15 | 2.052 (2) | C24—C25 | 1.413 (3) |
Fe1—C21 | 2.045 (2) | C24—H24 | 0.95 |
Fe1—C22 | 2.049 (2) | C25—H25 | 0.95 |
Fe1—C23 | 2.060 (2) | N31—C36 | 1.341 (3) |
Fe1—C24 | 2.054 (2) | N31—C32 | 1.343 (3) |
Fe1—C25 | 2.048 (2) | C32—C33 | 1.384 (3) |
O11—C16 | 1.323 (3) | C32—H32 | 0.95 |
O11—H11 | 0.84 | C33—C34 | 1.392 (3) |
O12—C16 | 1.216 (3) | C33—H33 | 0.95 |
C11—C12 | 1.433 (3) | C34—C35 | 1.398 (3) |
C11—C15 | 1.434 (3) | C34—C44 | 1.484 (3) |
C11—C16 | 1.474 (3) | C35—C36 | 1.379 (3) |
C12—C13 | 1.419 (3) | C35—H35 | 0.95 |
C12—H12 | 0.95 | C36—H36 | 0.95 |
C13—C14 | 1.426 (3) | N41—C46 | 1.334 (3) |
C13—H13 | 0.95 | N41—C42 | 1.349 (3) |
C14—C15 | 1.411 (3) | C42—C43 | 1.377 (3) |
C14—H14 | 0.95 | C42—H42 | 0.95 |
C15—H15 | 0.95 | C43—C44 | 1.397 (3) |
O21—C26 | 1.322 (3) | C43—H43 | 0.95 |
O21—H21 | 0.84 | C44—C45 | 1.398 (3) |
O22—C26 | 1.225 (3) | C45—C46 | 1.380 (3) |
C21—C25 | 1.426 (3) | C45—H45 | 0.95 |
C21—C22 | 1.434 (3) | C46—H46 | 0.95 |
C21—C26 | 1.471 (3) | ||
C16—O11—H11 | 109.5 | O22—C26—O21 | 123.8 (2) |
C12—C11—C15 | 107.57 (19) | O22—C26—C21 | 122.4 (2) |
C12—C11—C16 | 127.4 (2) | O21—C26—C21 | 113.81 (19) |
C15—C11—C16 | 124.84 (19) | C36—N31—C32 | 117.1 (2) |
C13—C12—C11 | 107.91 (19) | N31—C32—C33 | 123.1 (2) |
C13—C12—H12 | 126.0 | N31—C32—H32 | 118.4 |
C11—C12—H12 | 126.0 | C33—C32—H32 | 118.4 |
C12—C13—C14 | 108.0 (2) | C32—C33—C34 | 119.8 (2) |
C12—C13—H13 | 126.0 | C32—C33—H33 | 120.1 |
C14—C13—H13 | 126.0 | C34—C33—H33 | 120.1 |
C15—C14—C13 | 108.5 (2) | C33—C34—C35 | 116.8 (2) |
C15—C14—H14 | 125.7 | C33—C34—C44 | 122.26 (19) |
C13—C14—H14 | 125.7 | C35—C34—C44 | 120.9 (2) |
C14—C15—C11 | 108.0 (2) | C36—C35—C34 | 119.8 (2) |
C14—C15—H15 | 126.0 | C36—C35—H35 | 120.1 |
C11—C15—H15 | 126.0 | C34—C35—H35 | 120.1 |
O12—C16—O11 | 123.7 (2) | N31—C36—C35 | 123.3 (2) |
O12—C16—C11 | 122.3 (2) | N31—C36—H36 | 118.3 |
O11—C16—C11 | 113.93 (18) | C35—C36—H36 | 118.3 |
C26—O21—H21 | 109.5 | C46—N41—C42 | 117.4 (2) |
C25—C21—C22 | 107.62 (19) | N41—C42—C43 | 123.0 (2) |
C25—C21—C26 | 125.3 (2) | N41—C42—H42 | 118.5 |
C22—C21—C26 | 127.1 (2) | C43—C42—H42 | 118.5 |
C23—C22—C21 | 107.72 (19) | C42—C43—C44 | 119.7 (2) |
C23—C22—H22 | 126.1 | C42—C43—H43 | 120.2 |
C21—C22—H22 | 126.1 | C44—C43—H43 | 120.2 |
C22—C23—C24 | 108.35 (19) | C43—C44—C45 | 117.0 (2) |
C22—C23—H23 | 125.8 | C43—C44—C34 | 122.1 (2) |
C24—C23—H23 | 125.8 | C45—C44—C34 | 121.0 (2) |
C25—C24—C23 | 108.3 (2) | C46—C45—C44 | 119.6 (2) |
C25—C24—H24 | 125.9 | C46—C45—H45 | 120.2 |
C23—C24—H24 | 125.9 | C44—C45—H45 | 120.2 |
C24—C25—C21 | 108.04 (19) | N41—C46—C45 | 123.3 (2) |
C24—C25—H25 | 126.0 | N41—C46—H46 | 118.3 |
C21—C25—H25 | 126.0 | C45—C46—H46 | 118.3 |
C15—C11—C12—C13 | 0.5 (2) | C22—C21—C26—O21 | −7.5 (3) |
C16—C11—C12—C13 | −174.8 (2) | C36—N31—C32—C33 | −0.1 (3) |
C11—C12—C13—C14 | −0.4 (2) | N31—C32—C33—C34 | −0.6 (3) |
C12—C13—C14—C15 | 0.2 (2) | C32—C33—C34—C35 | 1.0 (3) |
C13—C14—C15—C11 | 0.1 (2) | C32—C33—C34—C44 | −179.58 (19) |
C12—C11—C15—C14 | −0.4 (2) | C33—C34—C35—C36 | −0.7 (3) |
C16—C11—C15—C14 | 175.06 (19) | C44—C34—C35—C36 | 179.84 (19) |
C12—C11—C16—O12 | 178.1 (2) | C32—N31—C36—C35 | 0.4 (3) |
C15—C11—C16—O12 | 3.6 (3) | C34—C35—C36—N31 | 0.0 (3) |
C12—C11—C16—O11 | −2.0 (3) | C46—N41—C42—C43 | 0.2 (3) |
C15—C11—C16—O11 | −176.55 (19) | N41—C42—C43—C44 | −0.3 (3) |
C25—C21—C22—C23 | 0.5 (2) | C42—C43—C44—C45 | 0.2 (3) |
C26—C21—C22—C23 | −179.62 (19) | C42—C43—C44—C34 | −179.8 (2) |
C21—C22—C23—C24 | −0.6 (2) | C33—C34—C44—C43 | −152.0 (2) |
C22—C23—C24—C25 | 0.5 (2) | C35—C34—C44—C43 | 27.5 (3) |
C23—C24—C25—C21 | −0.2 (2) | C33—C34—C44—C45 | 28.0 (3) |
C22—C21—C25—C24 | −0.2 (2) | C35—C34—C44—C45 | −152.5 (2) |
C26—C21—C25—C24 | 179.94 (19) | C43—C44—C45—C46 | 0.0 (3) |
C25—C21—C26—O22 | −9.2 (3) | C34—C44—C45—C46 | 179.98 (19) |
C22—C21—C26—O22 | 170.9 (2) | C42—N41—C46—C45 | 0.0 (3) |
C25—C21—C26—O21 | 172.33 (19) | C44—C45—C46—N41 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N31 | 0.84 | 1.83 | 2.674 (2) | 179 |
O21—H21···N41i | 0.84 | 1.79 | 2.629 (2) | 177 |
C46—H46···O12ii | 0.95 | 2.30 | 3.232 (3) | 169 |
Symmetry codes: (i) x−2, y, z+1; (ii) −x+2, −y, −z. |
2(C8H20N)·C12H8FeO4 | Z = 1 |
Mr = 532.53 | F(000) = 288 |
Triclinic, P1 | Dx = 1.227 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3490 (2) Å | Cell parameters from 2871 reflections |
b = 9.6089 (4) Å | θ = 3.8–27.6° |
c = 12.1674 (4) Å | µ = 0.56 mm−1 |
α = 98.738 (2)° | T = 150 K |
β = 100.380 (2)° | Needle, red |
γ = 91.2290 (17)° | 0.26 × 0.08 × 0.06 mm |
V = 720.76 (4) Å3 |
Kappa-CCD diffractometer | 3268 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2589 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ scans, and ω scans with κ offsets | θmax = 27.6°, θmin = 3.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→8 |
Tmin = 0.869, Tmax = 0.967 | k = −12→12 |
8932 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2)P)2 + 0.2558P] where P = (Fo2 + 2Fc2)/3 |
3268 reflections | (Δ/σ)max < 0.001 |
162 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
2(C8H20N)·C12H8FeO4 | γ = 91.2290 (17)° |
Mr = 532.53 | V = 720.76 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.3490 (2) Å | Mo Kα radiation |
b = 9.6089 (4) Å | µ = 0.56 mm−1 |
c = 12.1674 (4) Å | T = 150 K |
α = 98.738 (2)° | 0.26 × 0.08 × 0.06 mm |
β = 100.380 (2)° |
Kappa-CCD diffractometer | 3268 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2589 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.967 | Rint = 0.052 |
8932 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.24 e Å−3 |
3268 reflections | Δρmin = −0.43 e Å−3 |
162 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.5000 | 0.5000 | 0.5000 | 0.02658 (13) | |
O1 | 0.9473 (2) | 0.72654 (15) | 0.43589 (13) | 0.0354 (3) | |
O2 | 0.6430 (2) | 0.83945 (13) | 0.42000 (11) | 0.0293 (3) | |
C11 | 0.6244 (3) | 0.5893 (2) | 0.38335 (15) | 0.0261 (4) | |
C12 | 0.3985 (3) | 0.5645 (2) | 0.34866 (16) | 0.0304 (4) | |
C13 | 0.3506 (4) | 0.4183 (2) | 0.33936 (17) | 0.0370 (5) | |
C14 | 0.5446 (4) | 0.3520 (2) | 0.36860 (17) | 0.0365 (5) | |
C15 | 0.7148 (3) | 0.4555 (2) | 0.39480 (16) | 0.0308 (5) | |
C16 | 0.7476 (3) | 0.7277 (2) | 0.41509 (15) | 0.0257 (4) | |
N1 | 1.2366 (3) | 0.92556 (17) | 0.41638 (13) | 0.0301 (4) | |
C2 | 1.1906 (3) | 0.9643 (2) | 0.30100 (17) | 0.0357 (5) | |
C3 | 0.9882 (3) | 1.0425 (2) | 0.28109 (16) | 0.0328 (5) | |
C4 | 0.9350 (4) | 1.0776 (2) | 0.16095 (16) | 0.0369 (5) | |
C5 | 0.7296 (4) | 1.1544 (2) | 0.14079 (16) | 0.0377 (5) | |
C6 | 0.6625 (4) | 1.1891 (2) | 0.02176 (16) | 0.0376 (5) | |
C7 | 0.4543 (4) | 1.2645 (2) | 0.00761 (17) | 0.0380 (5) | |
C8 | 0.3851 (4) | 1.3087 (3) | −0.10810 (18) | 0.0428 (5) | |
C9 | 0.1770 (4) | 1.3844 (3) | −0.1190 (2) | 0.0508 (6) | |
H12 | 0.2975 | 0.6341 | 0.3343 | 0.036* | |
H13 | 0.2119 | 0.3725 | 0.3173 | 0.044* | |
H14 | 0.5583 | 0.2541 | 0.3704 | 0.044* | |
H15 | 0.8626 | 0.4395 | 0.4162 | 0.037* | |
H1A | 1.2503 | 1.0051 | 0.4689 | 0.045* | |
H1B | 1.3607 | 0.8794 | 0.4252 | 0.045* | |
H1C | 1.1271 | 0.8685 | 0.4257 | 0.045* | |
H2A | 1.1773 | 0.8775 | 0.2443 | 0.043* | |
H2B | 1.3123 | 1.0238 | 0.2904 | 0.043* | |
H3A | 1.0039 | 1.1312 | 0.3359 | 0.039* | |
H3B | 0.8676 | 0.9846 | 0.2948 | 0.039* | |
H4A | 1.0545 | 1.1368 | 0.1476 | 0.044* | |
H4B | 0.9214 | 0.9891 | 0.1060 | 0.044* | |
H5A | 0.7461 | 1.2435 | 0.1951 | 0.045* | |
H5B | 0.6125 | 1.0960 | 0.1575 | 0.045* | |
H6A | 0.7772 | 1.2494 | 0.0048 | 0.045* | |
H6B | 0.6456 | 1.1007 | −0.0334 | 0.045* | |
H7A | 0.4697 | 1.3496 | 0.0661 | 0.046* | |
H7B | 0.3393 | 1.2018 | 0.0214 | 0.046* | |
H8A | 0.4997 | 1.3714 | −0.1223 | 0.051* | |
H8B | 0.3680 | 1.2238 | −0.1669 | 0.051* | |
H9A | 0.0616 | 1.3219 | −0.1075 | 0.076* | |
H9B | 0.1416 | 1.4107 | −0.1946 | 0.076* | |
H9C | 0.1932 | 1.4694 | −0.0618 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0305 (3) | 0.0229 (2) | 0.0289 (2) | −0.00310 (17) | 0.01549 (17) | 0.00093 (15) |
O1 | 0.0202 (8) | 0.0331 (8) | 0.0558 (9) | −0.0014 (6) | 0.0097 (7) | 0.0134 (7) |
O2 | 0.0237 (7) | 0.0253 (7) | 0.0400 (7) | −0.0013 (6) | 0.0081 (6) | 0.0064 (6) |
C11 | 0.0272 (10) | 0.0277 (10) | 0.0253 (9) | −0.0028 (8) | 0.0114 (8) | 0.0031 (7) |
C12 | 0.0282 (11) | 0.0315 (10) | 0.0312 (10) | −0.0066 (9) | 0.0087 (8) | 0.0011 (8) |
C13 | 0.0414 (13) | 0.0350 (11) | 0.0342 (11) | −0.0144 (10) | 0.0159 (9) | −0.0039 (9) |
C14 | 0.0532 (15) | 0.0235 (10) | 0.0375 (11) | −0.0051 (10) | 0.0268 (10) | −0.0016 (8) |
C15 | 0.0370 (12) | 0.0265 (10) | 0.0341 (10) | 0.0028 (9) | 0.0211 (9) | 0.0035 (8) |
C16 | 0.0256 (11) | 0.0294 (10) | 0.0251 (9) | −0.0002 (8) | 0.0104 (8) | 0.0074 (8) |
N1 | 0.0243 (9) | 0.0280 (9) | 0.0389 (9) | −0.0017 (7) | 0.0094 (7) | 0.0044 (7) |
C2 | 0.0346 (12) | 0.0377 (12) | 0.0374 (11) | −0.0034 (10) | 0.0145 (9) | 0.0049 (9) |
C3 | 0.0340 (12) | 0.0333 (11) | 0.0325 (10) | −0.0024 (9) | 0.0107 (9) | 0.0051 (8) |
C4 | 0.0427 (13) | 0.0383 (12) | 0.0323 (10) | −0.0006 (10) | 0.0153 (9) | 0.0040 (9) |
C5 | 0.0448 (13) | 0.0425 (12) | 0.0284 (10) | 0.0009 (10) | 0.0126 (9) | 0.0069 (9) |
C6 | 0.0483 (14) | 0.0391 (12) | 0.0274 (10) | 0.0005 (10) | 0.0128 (9) | 0.0045 (9) |
C7 | 0.0433 (13) | 0.0423 (12) | 0.0301 (10) | −0.0025 (10) | 0.0101 (9) | 0.0072 (9) |
C8 | 0.0527 (15) | 0.0455 (13) | 0.0329 (11) | 0.0022 (11) | 0.0119 (10) | 0.0099 (9) |
C9 | 0.0487 (15) | 0.0605 (16) | 0.0443 (13) | 0.0004 (13) | 0.0058 (11) | 0.0153 (12) |
Fe1—C11i | 2.0297 (18) | N1—H1C | 0.91 |
Fe1—C11 | 2.0297 (18) | C2—C3 | 1.503 (3) |
Fe1—C12i | 2.031 (2) | C2—H2A | 0.99 |
Fe1—C12 | 2.031 (2) | C2—H2B | 0.99 |
Fe1—C14 | 2.0364 (18) | C3—C4 | 1.530 (3) |
Fe1—C14i | 2.0365 (18) | C3—H3A | 0.99 |
Fe1—C15 | 2.0416 (17) | C3—H3B | 0.99 |
Fe1—C15i | 2.0416 (17) | C4—C5 | 1.512 (3) |
Fe1—C13i | 2.042 (2) | C4—H4A | 0.99 |
Fe1—C13 | 2.042 (2) | C4—H4B | 0.99 |
O1—C16 | 1.248 (2) | C5—C6 | 1.524 (3) |
O2—C16 | 1.274 (2) | C5—H5A | 0.99 |
C11—C12 | 1.424 (3) | C5—H5B | 0.99 |
C11—C15 | 1.435 (3) | C6—C7 | 1.516 (3) |
C11—C16 | 1.489 (3) | C6—H6A | 0.99 |
C12—C13 | 1.415 (3) | C6—H6B | 0.99 |
C12—H12 | 0.95 | C7—C8 | 1.524 (3) |
C13—C14 | 1.412 (3) | C7—H7A | 0.99 |
C13—H13 | 0.95 | C7—H7B | 0.99 |
C14—C15 | 1.411 (3) | C8—C9 | 1.517 (3) |
C14—H14 | 0.95 | C8—H8A | 0.99 |
C15—H15 | 0.95 | C8—H8B | 0.99 |
N1—C2 | 1.487 (3) | C9—H9A | 0.98 |
N1—H1A | 0.91 | C9—H9B | 0.98 |
N1—H1B | 0.91 | C9—H9C | 0.98 |
C12—C11—C15 | 107.36 (18) | C5—C4—C3 | 112.36 (16) |
C12—C11—C16 | 127.73 (17) | C5—C4—H4A | 109.1 |
C15—C11—C16 | 124.59 (18) | C3—C4—H4A | 109.1 |
C13—C12—C11 | 108.14 (19) | C5—C4—H4B | 109.1 |
C13—C12—H12 | 125.9 | C3—C4—H4B | 109.1 |
C11—C12—H12 | 125.9 | H4A—C4—H4B | 107.9 |
C14—C13—C12 | 108.15 (19) | C4—C5—C6 | 115.42 (17) |
C14—C13—H13 | 125.9 | C4—C5—H5A | 108.4 |
C12—C13—H13 | 125.9 | C6—C5—H5A | 108.4 |
C15—C14—C13 | 108.66 (18) | C4—C5—H5B | 108.4 |
C15—C14—H14 | 125.7 | C6—C5—H5B | 108.4 |
C13—C14—H14 | 125.7 | H5A—C5—H5B | 107.5 |
C14—C15—C11 | 107.69 (18) | C7—C6—C5 | 112.40 (17) |
C14—C15—H15 | 126.2 | C7—C6—H6A | 109.1 |
C11—C15—H15 | 126.2 | C5—C6—H6A | 109.1 |
O1—C16—O2 | 124.14 (18) | C7—C6—H6B | 109.1 |
O1—C16—C11 | 117.73 (16) | C5—C6—H6B | 109.1 |
O2—C16—C11 | 118.14 (17) | H6A—C6—H6B | 107.9 |
C2—N1—H1A | 109.5 | C6—C7—C8 | 114.74 (17) |
C2—N1—H1B | 109.5 | C6—C7—H7A | 108.6 |
H1A—N1—H1B | 109.5 | C8—C7—H7A | 108.6 |
C2—N1—H1C | 109.5 | C6—C7—H7B | 108.6 |
H1A—N1—H1C | 109.5 | C8—C7—H7B | 108.6 |
H1B—N1—H1C | 109.5 | H7A—C7—H7B | 107.6 |
N1—C2—C3 | 112.27 (16) | C9—C8—C7 | 113.28 (18) |
N1—C2—H2A | 109.2 | C9—C8—H8A | 108.9 |
C3—C2—H2A | 109.2 | C7—C8—H8A | 108.9 |
N1—C2—H2B | 109.2 | C9—C8—H8B | 108.9 |
C3—C2—H2B | 109.2 | C7—C8—H8B | 108.9 |
H2A—C2—H2B | 107.9 | H8A—C8—H8B | 107.7 |
C2—C3—C4 | 112.55 (16) | C8—C9—H9A | 109.5 |
C2—C3—H3A | 109.1 | C8—C9—H9B | 109.5 |
C4—C3—H3A | 109.1 | H9A—C9—H9B | 109.5 |
C2—C3—H3B | 109.1 | C8—C9—H9C | 109.5 |
C4—C3—H3B | 109.1 | H9A—C9—H9C | 109.5 |
H3A—C3—H3B | 107.8 | H9B—C9—H9C | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2ii | 0.91 | 1.88 | 2.767 (2) | 165 |
N1—H1B···O2iii | 0.91 | 1.85 | 2.721 (2) | 159 |
N1—H1C···O1 | 0.91 | 1.79 | 2.689 (2) | 168 |
Symmetry codes: (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z. |
C12H9FeO4·C5H12N | F(000) = 752 |
Mr = 359.20 | Dx = 1.542 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2442 reflections |
a = 5.9880 (3) Å | θ = 3.5–25.1° |
b = 19.4750 (12) Å | µ = 1.00 mm−1 |
c = 13.4340 (9) Å | T = 150 K |
β = 99.058 (3)° | Needle, orange |
V = 1547.09 (16) Å3 | 0.30 × 0.15 × 0.12 mm |
Z = 4 |
Kappa-CCD diffractometer | 2694 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1926 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ϕ scans,and ω scans with κ offsets | θmax = 25.1°, θmin = 3.5° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→7 |
Tmin = 0.755, Tmax = 0.890 | k = 0→23 |
7828 measured reflections | l = −16→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0363P)2 + 0.139P] where P = (Fo2 + 2Fc2)/3 |
2694 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
C12H9FeO4·C5H12N | V = 1547.09 (16) Å3 |
Mr = 359.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.9880 (3) Å | µ = 1.00 mm−1 |
b = 19.4750 (12) Å | T = 150 K |
c = 13.4340 (9) Å | 0.30 × 0.15 × 0.12 mm |
β = 99.058 (3)° |
Kappa-CCD diffractometer | 2694 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 1926 reflections with I > 2σ(I) |
Tmin = 0.755, Tmax = 0.890 | Rint = 0.068 |
7828 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.56 e Å−3 |
2694 reflections | Δρmin = −0.66 e Å−3 |
210 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.5413 (0.0092) x - 4.9557 (0.0327) y + 12.5824 (0.0078) z = 2.4597 (0.0143) * -0.0006 (0.0007) C11 * 0.0020 (0.0026) C16 * -0.0007 (0.0009) O11 * -0.0007 (0.0010) O12 Rms deviation of fitted atoms = 0.0011 - 0.8059 (0.0087) x - 5.4999 (0.0191) y + 12.8852 (0.0039) z = 1.6580 (0.0118) Angle to previous plane (with approximate e.s.d.) = 13.04 (11) * 0.0372 (0.0027) C11 * 0.0223 (0.0022) C12 * -0.0247 (0.0022) C13 * -0.0150 (0.0022) C14 * 0.0167 (0.0022) C15 * -0.0364 (0.0018) C16 - 1.6401 (0.0013) Fe1 Rms deviation of fitted atoms = 0.0268 1.1873 (0.0086) x + 4.6054 (0.0205) y - 13.0383 (0.0034) z = 1.2893 (0.0110) Angle to previous plane (with approximate e.s.d.) = 4.50 (9) * 0.0080 (0.0027) C21 * 0.0028 (0.0022) C22 * -0.0041 (0.0022) C23 * -0.0016 (0.0022) C24 * 0.0011 (0.0021) C25 * -0.0063 (0.0017) C26 - 1.6454 (0.0013) Fe1 Rms deviation of fitted atoms = 0.0047 1.2813 (0.0089) x + 4.5169 (0.0339) y - 13.0412 (0.0057) z = 1.2887 (0.0231) Angle to previous plane (with approximate e.s.d.) = 0.95 (11) * 0.0026 (0.0008) C21 * -0.0089 (0.0026) C26 * 0.0029 (0.0009) O21 * 0.0034 (0.0010) O22 Rms deviation of fitted atoms = 0.0052 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.40895 (8) | 0.51052 (3) | 0.24488 (3) | 0.02042 (17) | |
O11 | 0.3972 (4) | 0.31674 (14) | 0.3031 (2) | 0.0318 (6) | |
O12 | 0.7474 (4) | 0.35619 (14) | 0.30357 (17) | 0.0286 (6) | |
O21 | 0.4328 (4) | 0.70154 (15) | 0.1865 (2) | 0.0365 (7) | |
O22 | 0.7901 (4) | 0.66341 (14) | 0.20833 (16) | 0.0290 (6) | |
C11 | 0.4700 (5) | 0.43238 (19) | 0.3455 (2) | 0.0206 (8) | |
C12 | 0.2404 (6) | 0.4552 (2) | 0.3397 (2) | 0.0234 (8) | |
C13 | 0.2431 (6) | 0.5254 (2) | 0.3662 (2) | 0.0262 (9) | |
C14 | 0.4730 (6) | 0.5463 (2) | 0.3903 (2) | 0.0251 (8) | |
C15 | 0.6128 (6) | 0.4893 (2) | 0.3772 (2) | 0.0229 (8) | |
C16 | 0.5474 (6) | 0.3641 (2) | 0.3155 (2) | 0.0235 (8) | |
C21 | 0.4918 (5) | 0.5861 (2) | 0.1523 (2) | 0.0231 (8) | |
C22 | 0.6216 (6) | 0.52565 (19) | 0.1432 (2) | 0.0233 (8) | |
C23 | 0.4703 (6) | 0.4713 (2) | 0.1107 (2) | 0.0281 (9) | |
C24 | 0.2453 (6) | 0.4978 (2) | 0.0994 (2) | 0.0270 (9) | |
C25 | 0.2580 (6) | 0.5682 (2) | 0.1252 (2) | 0.0269 (9) | |
C26 | 0.5852 (6) | 0.6531 (2) | 0.1856 (2) | 0.0247 (8) | |
N1 | 0.9448 (4) | 0.26877 (17) | 0.1826 (2) | 0.0272 (8) | |
C2 | 1.0158 (6) | 0.3250 (2) | 0.1200 (3) | 0.0327 (9) | |
C3 | 1.1703 (6) | 0.2980 (2) | 0.0494 (3) | 0.0346 (10) | |
C4 | 1.0587 (6) | 0.2405 (2) | −0.0159 (3) | 0.0354 (10) | |
C5 | 0.9776 (6) | 0.1844 (2) | 0.0489 (3) | 0.0331 (10) | |
C6 | 0.8275 (6) | 0.2126 (2) | 0.1191 (3) | 0.0327 (9) | |
H11 | 0.4601 | 0.2786 | 0.2987 | 0.048* | 0.50 |
H21 | 0.4960 | 0.7401 | 0.1889 | 0.055* | 0.50 |
H12 | 0.1092 | 0.4278 | 0.3213 | 0.028* | |
H13 | 0.1143 | 0.5536 | 0.3677 | 0.031* | |
H14 | 0.5241 | 0.5909 | 0.4116 | 0.030* | |
H15 | 0.7734 | 0.4891 | 0.3876 | 0.028* | |
H22 | 0.7818 | 0.5224 | 0.1565 | 0.028* | |
H23 | 0.5113 | 0.4253 | 0.0986 | 0.034* | |
H24 | 0.1106 | 0.4725 | 0.0782 | 0.032* | |
H25 | 0.1333 | 0.5984 | 0.1247 | 0.032* | |
H1A | 0.8492 | 0.2861 | 0.2238 | 0.033* | |
H1B | 1.0699 | 0.2511 | 0.2230 | 0.033* | |
H2A | 1.0961 | 0.3608 | 0.1643 | 0.039* | |
H2B | 0.8805 | 0.3463 | 0.0800 | 0.039* | |
H3A | 1.2088 | 0.3358 | 0.0059 | 0.041* | |
H3B | 1.3125 | 0.2810 | 0.0895 | 0.041* | |
H4A | 1.1679 | 0.2208 | −0.0563 | 0.043* | |
H4B | 0.9286 | 0.2588 | −0.0630 | 0.043* | |
H5A | 0.8932 | 0.1494 | 0.0046 | 0.040* | |
H5B | 1.1101 | 0.1617 | 0.0888 | 0.040* | |
H6A | 0.6863 | 0.2306 | 0.0794 | 0.039* | |
H6B | 0.7866 | 0.1754 | 0.1631 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0210 (3) | 0.0192 (3) | 0.0213 (3) | 0.0000 (2) | 0.00432 (18) | 0.0012 (2) |
O11 | 0.0259 (14) | 0.0178 (17) | 0.0525 (16) | 0.0016 (11) | 0.0086 (12) | 0.0021 (13) |
O12 | 0.0230 (14) | 0.0246 (18) | 0.0396 (14) | 0.0021 (11) | 0.0099 (10) | −0.0014 (12) |
O21 | 0.0274 (14) | 0.0218 (19) | 0.0606 (17) | −0.0023 (12) | 0.0077 (12) | 0.0025 (14) |
O22 | 0.0240 (14) | 0.0280 (18) | 0.0349 (13) | −0.0022 (11) | 0.0037 (10) | 0.0009 (12) |
C11 | 0.0257 (19) | 0.016 (2) | 0.0203 (17) | −0.0012 (15) | 0.0058 (13) | −0.0017 (15) |
C12 | 0.0266 (19) | 0.021 (2) | 0.0241 (17) | −0.0010 (16) | 0.0094 (14) | 0.0003 (15) |
C13 | 0.028 (2) | 0.023 (3) | 0.0296 (19) | 0.0054 (16) | 0.0096 (14) | −0.0031 (16) |
C14 | 0.036 (2) | 0.017 (2) | 0.0229 (17) | −0.0042 (17) | 0.0071 (14) | −0.0026 (16) |
C15 | 0.0254 (18) | 0.022 (2) | 0.0216 (17) | 0.0002 (16) | 0.0059 (13) | −0.0007 (15) |
C16 | 0.026 (2) | 0.023 (3) | 0.0213 (17) | −0.0004 (16) | 0.0050 (14) | 0.0051 (15) |
C21 | 0.0256 (19) | 0.023 (2) | 0.0209 (17) | −0.0005 (15) | 0.0037 (14) | 0.0065 (16) |
C22 | 0.031 (2) | 0.023 (3) | 0.0180 (16) | −0.0029 (16) | 0.0077 (13) | 0.0015 (15) |
C23 | 0.041 (2) | 0.021 (3) | 0.0232 (18) | 0.0000 (17) | 0.0080 (15) | 0.0002 (16) |
C24 | 0.032 (2) | 0.025 (3) | 0.0220 (17) | −0.0047 (16) | −0.0026 (14) | 0.0035 (16) |
C25 | 0.028 (2) | 0.024 (3) | 0.0277 (18) | −0.0002 (16) | 0.0014 (14) | 0.0088 (17) |
C26 | 0.031 (2) | 0.022 (2) | 0.0226 (17) | 0.0016 (16) | 0.0097 (15) | 0.0080 (15) |
N1 | 0.0235 (16) | 0.030 (2) | 0.0298 (16) | 0.0051 (13) | 0.0076 (12) | 0.0027 (14) |
C2 | 0.035 (2) | 0.030 (3) | 0.033 (2) | −0.0021 (18) | 0.0044 (16) | 0.0000 (18) |
C3 | 0.037 (2) | 0.038 (3) | 0.031 (2) | −0.0081 (19) | 0.0099 (16) | −0.0007 (18) |
C4 | 0.041 (2) | 0.037 (3) | 0.030 (2) | −0.001 (2) | 0.0106 (16) | 0.0023 (18) |
C5 | 0.042 (2) | 0.028 (3) | 0.029 (2) | 0.0018 (18) | 0.0056 (16) | −0.0008 (17) |
C6 | 0.029 (2) | 0.034 (3) | 0.035 (2) | −0.0050 (17) | 0.0043 (15) | 0.0009 (18) |
Fe1—C11 | 2.030 (3) | C21—C25 | 1.433 (5) |
Fe1—C12 | 2.051 (3) | C21—C26 | 1.462 (5) |
Fe1—C13 | 2.058 (3) | C22—C23 | 1.416 (5) |
Fe1—C14 | 2.053 (3) | C22—H22 | 0.95 |
Fe1—C15 | 2.033 (3) | C23—C24 | 1.429 (5) |
Fe1—C21 | 2.038 (3) | C23—H23 | 0.95 |
Fe1—C22 | 2.030 (3) | C24—C25 | 1.413 (5) |
Fe1—C23 | 2.043 (3) | C24—H24 | 0.95 |
Fe1—C24 | 2.058 (3) | C25—H25 | 0.95 |
Fe1—C25 | 2.051 (3) | N1—C2 | 1.484 (5) |
O11—C16 | 1.281 (4) | N1—C6 | 1.492 (5) |
O11—H11 | 0.84 | N1—H1A | 0.92 |
O12—C16 | 1.243 (4) | N1—H1B | 0.92 |
O21—C26 | 1.314 (4) | C2—C3 | 1.519 (5) |
O21—H21 | 0.84 | C2—H2A | 0.99 |
O22—C26 | 1.233 (4) | C2—H2B | 0.99 |
C11—C15 | 1.423 (5) | C3—C4 | 1.512 (5) |
C11—C12 | 1.436 (4) | C3—H3A | 0.99 |
C11—C16 | 1.484 (5) | C3—H3B | 0.99 |
C12—C13 | 1.412 (5) | C4—C5 | 1.522 (5) |
C12—H12 | 0.95 | C4—H4A | 0.99 |
C13—C14 | 1.423 (5) | C4—H4B | 0.99 |
C13—H13 | 0.95 | C5—C6 | 1.506 (5) |
C14—C15 | 1.418 (5) | C5—H5A | 0.99 |
C14—H14 | 0.95 | C5—H5B | 0.99 |
C15—H15 | 0.95 | C6—H6A | 0.99 |
C21—C22 | 1.426 (5) | C6—H6B | 0.99 |
C16—O11—H11 | 109.5 | O21—C26—C21 | 114.3 (3) |
C26—O21—H21 | 109.5 | C2—N1—C6 | 111.6 (3) |
C15—C11—C12 | 107.5 (3) | C2—N1—H1A | 109.3 |
C15—C11—C16 | 125.5 (3) | C6—N1—H1A | 109.3 |
C12—C11—C16 | 126.8 (3) | C2—N1—H1B | 109.3 |
C13—C12—C11 | 108.2 (3) | C6—N1—H1B | 109.3 |
C13—C12—H12 | 125.9 | H1A—N1—H1B | 108.0 |
C11—C12—H12 | 125.9 | N1—C2—C3 | 110.8 (3) |
C12—C13—C14 | 107.9 (3) | N1—C2—H2A | 109.5 |
C12—C13—H13 | 126.1 | C3—C2—H2A | 109.5 |
C14—C13—H13 | 126.1 | N1—C2—H2B | 109.5 |
C15—C14—C13 | 108.4 (3) | C3—C2—H2B | 109.5 |
C15—C14—H14 | 125.8 | H2A—C2—H2B | 108.1 |
C13—C14—H14 | 125.8 | C4—C3—C2 | 111.2 (3) |
C14—C15—C11 | 108.0 (3) | C4—C3—H3A | 109.4 |
C14—C15—H15 | 126.0 | C2—C3—H3A | 109.4 |
C11—C15—H15 | 126.0 | C4—C3—H3B | 109.4 |
O12—C16—O11 | 124.4 (4) | C2—C3—H3B | 109.4 |
O12—C16—C11 | 119.7 (3) | H3A—C3—H3B | 108.0 |
O11—C16—C11 | 116.0 (3) | C3—C4—C5 | 110.6 (3) |
C22—C21—C25 | 107.6 (3) | C3—C4—H4A | 109.5 |
C22—C21—C26 | 125.2 (3) | C5—C4—H4A | 109.5 |
C25—C21—C26 | 127.3 (3) | C3—C4—H4B | 109.5 |
C23—C22—C21 | 108.2 (3) | C5—C4—H4B | 109.5 |
C23—C22—H22 | 125.9 | H4A—C4—H4B | 108.1 |
C21—C22—H22 | 125.9 | C6—C5—C4 | 111.9 (3) |
C22—C23—C24 | 108.0 (3) | C6—C5—H5A | 109.2 |
C22—C23—H23 | 126.0 | C4—C5—H5A | 109.2 |
C24—C23—H23 | 126.0 | C6—C5—H5B | 109.2 |
C25—C24—C23 | 108.1 (3) | C4—C5—H5B | 109.2 |
C25—C24—H24 | 125.9 | H5A—C5—H5B | 107.9 |
C23—C24—H24 | 125.9 | N1—C6—C5 | 110.6 (3) |
C24—C25—C21 | 108.1 (3) | N1—C6—H6A | 109.5 |
C24—C25—H25 | 126.0 | C5—C6—H6A | 109.5 |
C21—C25—H25 | 126.0 | N1—C6—H6B | 109.5 |
O22—C26—O21 | 123.1 (4) | C5—C6—H6B | 109.5 |
O22—C26—C21 | 122.6 (3) | H6A—C6—H6B | 108.1 |
C15—C11—C12—C13 | 0.8 (4) | C22—C23—C24—C25 | −0.2 (4) |
C16—C11—C12—C13 | −174.2 (3) | C23—C24—C25—C21 | 0.3 (4) |
C11—C12—C13—C14 | −1.0 (4) | C22—C21—C25—C24 | −0.3 (4) |
C12—C13—C14—C15 | 0.9 (4) | C26—C21—C25—C24 | −179.1 (3) |
C13—C14—C15—C11 | −0.4 (4) | C22—C21—C26—O22 | 0.7 (5) |
C12—C11—C15—C14 | −0.2 (4) | C25—C21—C26—O22 | 179.3 (3) |
C16—C11—C15—C14 | 174.8 (3) | C22—C21—C26—O21 | 178.9 (3) |
C15—C11—C16—O12 | −9.9 (5) | C25—C21—C26—O21 | −2.5 (5) |
C12—C11—C16—O12 | 164.2 (3) | C6—N1—C2—C3 | −57.8 (4) |
C15—C11—C16—O11 | 170.5 (3) | N1—C2—C3—C4 | 56.0 (4) |
C12—C11—C16—O11 | −15.4 (5) | C2—C3—C4—C5 | −53.7 (4) |
C25—C21—C22—C23 | 0.1 (4) | C3—C4—C5—C6 | 53.9 (4) |
C26—C21—C22—C23 | 178.9 (3) | C2—N1—C6—C5 | 57.5 (4) |
C21—C22—C23—C24 | 0.1 (4) | C4—C5—C6—N1 | −55.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O21i | 0.84 | 1.63 | 2.459 (4) | 168 |
O21—H21···O11ii | 0.84 | 1.62 | 2.459 (4) | 176 |
N1—H1A···O12 | 0.92 | 1.89 | 2.746 (4) | 153 |
N1—H1B···O22iii | 0.92 | 2.06 | 2.854 (4) | 144 |
N1—H1B···O11iv | 0.92 | 2.44 | 3.074 (4) | 126 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) x+1, y, z. |
2(C12H24N)·2(C12H9FeO4)·C4H8O | Z = 2 |
Mr = 982.83 | F(000) = 1048 |
Triclinic, P1 | Dx = 1.335 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3588 (2) Å | Cell parameters from 9949 reflections |
b = 11.9612 (2) Å | θ = 2.7–27.5° |
c = 22.7731 (5) Å | µ = 0.65 mm−1 |
α = 74.9690 (8)° | T = 150 K |
β = 78.0660 (8)° | Plate, colourless |
γ = 64.459 (1)° | 0.26 × 0.20 × 0.08 mm |
V = 2444.18 (8) Å3 |
Kappa-CCD diffractometer | 11044 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 8558 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→13 |
Tmin = 0.849, Tmax = 0.950 | k = −13→15 |
27832 measured reflections | l = −28→29 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0239P)2 + 1.6289P] where P = (Fo2 + 2Fc2)/3 |
11044 reflections | (Δ/σ)max = 0.001 |
603 parameters | Δρmax = 0.57 e Å−3 |
10 restraints | Δρmin = −0.58 e Å−3 |
2(C12H24N)·2(C12H9FeO4)·C4H8O | γ = 64.459 (1)° |
Mr = 982.83 | V = 2444.18 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.3588 (2) Å | Mo Kα radiation |
b = 11.9612 (2) Å | µ = 0.65 mm−1 |
c = 22.7731 (5) Å | T = 150 K |
α = 74.9690 (8)° | 0.26 × 0.20 × 0.08 mm |
β = 78.0660 (8)° |
Kappa-CCD diffractometer | 11044 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 8558 reflections with I > 2σ(I) |
Tmin = 0.849, Tmax = 0.950 | Rint = 0.041 |
27832 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 10 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.57 e Å−3 |
11044 reflections | Δρmin = −0.58 e Å−3 |
603 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.03245 (3) | 0.12869 (3) | 0.370175 (12) | 0.01792 (8) | |
O11 | 0.12239 (17) | 0.06052 (18) | 0.21144 (7) | 0.0397 (4) | |
O12 | 0.32174 (15) | −0.05894 (16) | 0.25783 (7) | 0.0304 (4) | |
C11 | 0.1014 (2) | −0.0064 (2) | 0.31891 (9) | 0.0225 (4) | |
C12 | −0.0526 (2) | 0.0460 (2) | 0.33075 (11) | 0.0278 (5) | |
C13 | −0.0879 (3) | 0.0224 (2) | 0.39513 (11) | 0.0329 (5) | |
C14 | 0.0424 (3) | −0.0432 (2) | 0.42303 (10) | 0.0319 (5) | |
C15 | 0.1594 (2) | −0.0606 (2) | 0.37613 (9) | 0.0254 (4) | |
C16 | 0.1804 (2) | 0.0031 (2) | 0.25759 (9) | 0.0247 (4) | |
O21 | −0.34311 (14) | 0.35434 (14) | 0.40857 (6) | 0.0249 (3) | |
O22 | −0.24112 (15) | 0.33844 (14) | 0.48926 (6) | 0.0253 (3) | |
C21 | −0.0901 (2) | 0.29670 (19) | 0.39814 (9) | 0.0199 (4) | |
C22 | 0.0462 (2) | 0.2399 (2) | 0.42194 (10) | 0.0229 (4) | |
C23 | 0.1567 (2) | 0.2232 (2) | 0.37190 (10) | 0.0250 (4) | |
C24 | 0.0885 (2) | 0.2705 (2) | 0.31726 (10) | 0.0260 (5) | |
C25 | −0.0623 (2) | 0.3148 (2) | 0.33285 (9) | 0.0221 (4) | |
C26 | −0.2344 (2) | 0.33094 (19) | 0.43497 (9) | 0.0198 (4) | |
Fe2 | 0.63588 (3) | 0.11465 (3) | 0.195009 (13) | 0.02250 (8) | |
O31 | 0.5031 (2) | 0.21839 (19) | 0.34718 (8) | 0.0436 (5) | |
O32 | 0.64905 (17) | 0.31658 (16) | 0.30278 (7) | 0.0304 (4) | |
C31 | 0.5440 (2) | 0.2642 (2) | 0.23888 (11) | 0.0306 (5) | |
C32 | 0.6258 (3) | 0.2945 (2) | 0.18338 (11) | 0.0377 (6) | |
C33 | 0.5695 (4) | 0.2832 (3) | 0.13454 (13) | 0.0520 (8) | |
C34 | 0.4544 (3) | 0.2474 (3) | 0.15952 (15) | 0.0600 (10) | |
C35 | 0.4374 (3) | 0.2338 (3) | 0.22408 (14) | 0.0477 (7) | |
C36 | 0.5633 (2) | 0.2624 (2) | 0.30180 (10) | 0.0270 (5) | |
O41 | 0.46241 (15) | −0.06496 (15) | 0.14921 (6) | 0.0253 (3) | |
O42 | 0.61331 (17) | −0.02892 (17) | 0.06996 (6) | 0.0345 (4) | |
C41 | 0.6686 (2) | −0.04426 (19) | 0.16732 (9) | 0.0208 (4) | |
C42 | 0.6471 (2) | −0.0623 (2) | 0.23285 (9) | 0.0265 (5) | |
C43 | 0.7568 (2) | −0.0439 (2) | 0.25246 (10) | 0.0269 (5) | |
C44 | 0.8455 (2) | −0.0133 (2) | 0.20003 (10) | 0.0273 (5) | |
C45 | 0.7919 (2) | −0.0141 (2) | 0.14758 (10) | 0.0248 (4) | |
C46 | 0.5755 (2) | −0.04586 (19) | 0.12602 (9) | 0.0206 (4) | |
N1 | 0.31194 (18) | −0.03105 (17) | 0.05214 (7) | 0.0222 (4) | |
C51 | 0.2853 (2) | −0.1480 (2) | 0.06043 (9) | 0.0221 (4) | |
C52 | 0.4286 (2) | −0.2569 (2) | 0.04948 (11) | 0.0315 (5) | |
C53 | 0.4099 (3) | −0.3804 (2) | 0.05894 (12) | 0.0397 (6) | |
C54 | 0.3284 (3) | −0.4082 (2) | 0.12098 (13) | 0.0426 (6) | |
C55 | 0.1872 (3) | −0.2973 (2) | 0.13105 (11) | 0.0358 (5) | |
C56 | 0.2094 (2) | −0.1764 (2) | 0.12371 (10) | 0.0275 (5) | |
C61 | 0.1857 (2) | 0.0877 (2) | 0.06407 (9) | 0.0231 (4) | |
C62 | 0.2378 (3) | 0.1942 (2) | 0.04921 (12) | 0.0356 (5) | |
C63 | 0.1150 (3) | 0.3137 (2) | 0.06687 (14) | 0.0468 (7) | |
C64 | −0.0158 (3) | 0.3507 (3) | 0.03413 (13) | 0.0459 (7) | |
C65 | −0.0620 (3) | 0.2415 (2) | 0.04533 (12) | 0.0375 (6) | |
C66 | 0.0609 (2) | 0.1224 (2) | 0.02820 (10) | 0.0281 (5) | |
N2 | −0.63244 (17) | 0.44786 (16) | 0.46051 (7) | 0.0179 (3) | |
C71 | −0.6584 (2) | 0.34962 (19) | 0.51241 (9) | 0.0197 (4) | |
C72 | −0.5645 (2) | 0.3253 (2) | 0.56173 (9) | 0.0228 (4) | |
C73 | −0.5786 (2) | 0.2219 (2) | 0.61526 (9) | 0.0279 (5) | |
C74 | −0.5446 (3) | 0.1008 (2) | 0.59320 (10) | 0.0328 (5) | |
C75 | −0.6430 (3) | 0.1278 (2) | 0.54523 (11) | 0.0311 (5) | |
C76 | −0.6265 (2) | 0.2292 (2) | 0.49090 (10) | 0.0260 (5) | |
C81 | −0.7119 (2) | 0.48702 (19) | 0.40520 (9) | 0.0190 (4) | |
C82 | −0.6713 (2) | 0.5891 (2) | 0.36063 (9) | 0.0261 (5) | |
C83 | −0.7492 (3) | 0.6353 (2) | 0.30357 (10) | 0.0345 (5) | |
C84 | −0.9115 (3) | 0.6822 (2) | 0.32008 (11) | 0.0347 (5) | |
C85 | −0.9512 (2) | 0.5802 (2) | 0.36476 (11) | 0.0312 (5) | |
C86 | −0.8746 (2) | 0.5335 (2) | 0.42240 (10) | 0.0255 (4) | |
O91A | 0.7958 (10) | 0.5121 (11) | 0.1629 (7) | 0.123 (3) | 0.50 |
C92A | 0.6765 (13) | 0.576 (2) | 0.2008 (9) | 0.089 (3) | 0.50 |
C93A | 0.6920 (19) | 0.6318 (16) | 0.2478 (10) | 0.055 (2) | 0.50 |
C94A | 0.848 (2) | 0.602 (2) | 0.2269 (6) | 0.051 (2) | 0.50 |
C95A | 0.9111 (11) | 0.5309 (9) | 0.1753 (4) | 0.091 (2) | 0.50 |
O91B | 0.7322 (10) | 0.5721 (11) | 0.1513 (8) | 0.123 (3) | 0.50 |
C92B | 0.6257 (14) | 0.602 (2) | 0.2008 (8) | 0.089 (3) | 0.50 |
C93B | 0.7154 (18) | 0.6061 (16) | 0.2416 (9) | 0.055 (2) | 0.50 |
C94B | 0.853 (2) | 0.619 (2) | 0.2136 (6) | 0.051 (2) | 0.50 |
C95B | 0.8442 (11) | 0.6088 (9) | 0.1500 (4) | 0.091 (2) | 0.50 |
H12 | 0.3613 | −0.0567 | 0.2217 | 0.046* | |
H12A | −0.1189 | 0.0886 | 0.3010 | 0.033* | |
H13 | −0.1824 | 0.0463 | 0.4160 | 0.040* | |
H14 | 0.0498 | −0.0707 | 0.4657 | 0.038* | |
H15 | 0.2586 | −0.1013 | 0.3819 | 0.030* | |
H22 | 0.0605 | 0.2170 | 0.4640 | 0.028* | |
H23 | 0.2574 | 0.1872 | 0.3746 | 0.030* | |
H24 | 0.1364 | 0.2721 | 0.2769 | 0.031* | |
H25 | −0.1328 | 0.3502 | 0.3049 | 0.027* | |
H32 | 0.6498 | 0.3206 | 0.3390 | 0.046* | |
H32A | 0.7042 | 0.3180 | 0.1798 | 0.045* | |
H33 | 0.6038 | 0.2973 | 0.0924 | 0.062* | |
H34 | 0.3967 | 0.2343 | 0.1368 | 0.072* | |
H35 | 0.3683 | 0.2091 | 0.2521 | 0.057* | |
H42 | 0.5726 | −0.0830 | 0.2586 | 0.032* | |
H43 | 0.7688 | −0.0509 | 0.2937 | 0.032* | |
H44 | 0.9264 | 0.0046 | 0.2000 | 0.033* | |
H45 | 0.8314 | 0.0026 | 0.1064 | 0.030* | |
H1A | 0.3522 | −0.0151 | 0.0126 | 0.027* | |
H1B | 0.3795 | −0.0481 | 0.0774 | 0.027* | |
H51 | 0.2224 | −0.1346 | 0.0291 | 0.027* | |
H52A | 0.4948 | −0.2665 | 0.0779 | 0.038* | |
H52B | 0.4724 | −0.2378 | 0.0072 | 0.038* | |
H53A | 0.3569 | −0.3755 | 0.0262 | 0.048* | |
H53B | 0.5058 | −0.4507 | 0.0558 | 0.048* | |
H54A | 0.3091 | −0.4836 | 0.1234 | 0.051* | |
H54B | 0.3887 | −0.4273 | 0.1537 | 0.051* | |
H55A | 0.1402 | −0.3163 | 0.1727 | 0.043* | |
H55B | 0.1224 | −0.2848 | 0.1013 | 0.043* | |
H56A | 0.1152 | −0.1053 | 0.1292 | 0.033* | |
H56B | 0.2681 | −0.1861 | 0.1554 | 0.033* | |
H61 | 0.1507 | 0.0752 | 0.1087 | 0.028* | |
H62A | 0.2699 | 0.2104 | 0.0050 | 0.043* | |
H62B | 0.3204 | 0.1697 | 0.0721 | 0.043* | |
H63A | 0.0881 | 0.2989 | 0.1116 | 0.056* | |
H63B | 0.1478 | 0.3837 | 0.0560 | 0.056* | |
H64A | 0.0075 | 0.3765 | −0.0103 | 0.055* | |
H64B | −0.0963 | 0.4238 | 0.0489 | 0.055* | |
H65A | −0.1423 | 0.2663 | 0.0210 | 0.045* | |
H65B | −0.0975 | 0.2234 | 0.0891 | 0.045* | |
H66A | 0.0283 | 0.0524 | 0.0379 | 0.034* | |
H66B | 0.0919 | 0.1374 | −0.0162 | 0.034* | |
H2A | −0.5354 | 0.4182 | 0.4476 | 0.021* | |
H2B | −0.6555 | 0.5190 | 0.4758 | 0.021* | |
H71 | −0.7617 | 0.3844 | 0.5297 | 0.024* | |
H72A | −0.5935 | 0.4042 | 0.5768 | 0.027* | |
H72B | −0.4627 | 0.2998 | 0.5439 | 0.027* | |
H73A | −0.6778 | 0.2515 | 0.6362 | 0.033* | |
H73B | −0.5116 | 0.2040 | 0.6451 | 0.033* | |
H74A | −0.4429 | 0.0669 | 0.5753 | 0.039* | |
H74B | −0.5584 | 0.0364 | 0.6283 | 0.039* | |
H75A | −0.7443 | 0.1566 | 0.5639 | 0.037* | |
H75B | −0.6189 | 0.0492 | 0.5307 | 0.037* | |
H76A | −0.5272 | 0.1980 | 0.4702 | 0.031* | |
H76B | −0.6936 | 0.2473 | 0.4611 | 0.031* | |
H81 | −0.6790 | 0.4125 | 0.3853 | 0.023* | |
H82A | −0.5660 | 0.5549 | 0.3488 | 0.031* | |
H82B | −0.6967 | 0.6609 | 0.3809 | 0.031* | |
H83A | −0.7253 | 0.7046 | 0.2764 | 0.041* | |
H83B | −0.7161 | 0.5655 | 0.2811 | 0.041* | |
H84A | −0.9462 | 0.7577 | 0.3387 | 0.042* | |
H84B | −0.9591 | 0.7068 | 0.2825 | 0.042* | |
H85A | −0.9252 | 0.5083 | 0.3445 | 0.037* | |
H85B | −1.0566 | 0.6142 | 0.3763 | 0.037* | |
H86A | −0.9078 | 0.6030 | 0.4451 | 0.031* | |
H86B | −0.8984 | 0.4638 | 0.4493 | 0.031* | |
H92A | 0.6307 | 0.5167 | 0.2218 | 0.107* | 0.50 |
H92B | 0.6071 | 0.6451 | 0.1740 | 0.107* | 0.50 |
H93A | 0.6749 | 0.5873 | 0.2899 | 0.066* | 0.50 |
H93B | 0.6321 | 0.7235 | 0.2434 | 0.066* | 0.50 |
H94A | 0.9037 | 0.5524 | 0.2622 | 0.061* | 0.50 |
H94B | 0.8614 | 0.6826 | 0.2140 | 0.061* | 0.50 |
H95A | 0.9467 | 0.5807 | 0.1391 | 0.109* | 0.50 |
H95B | 0.9915 | 0.4492 | 0.1878 | 0.109* | 0.50 |
H92C | 0.5881 | 0.5356 | 0.2180 | 0.107* | 0.50 |
H92D | 0.5451 | 0.6847 | 0.1901 | 0.107* | 0.50 |
H93C | 0.7387 | 0.5278 | 0.2732 | 0.066* | 0.50 |
H93D | 0.6570 | 0.6777 | 0.2628 | 0.066* | 0.50 |
H94C | 0.9375 | 0.5492 | 0.2320 | 0.061* | 0.50 |
H94D | 0.8516 | 0.7012 | 0.2151 | 0.061* | 0.50 |
H95C | 0.8266 | 0.6914 | 0.1221 | 0.109* | 0.50 |
H95D | 0.9364 | 0.5459 | 0.1346 | 0.109* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01794 (14) | 0.02138 (16) | 0.01627 (14) | −0.00914 (12) | 0.00154 (10) | −0.00702 (11) |
O11 | 0.0310 (9) | 0.0623 (12) | 0.0193 (8) | −0.0093 (8) | −0.0044 (7) | −0.0127 (8) |
O12 | 0.0217 (7) | 0.0444 (10) | 0.0191 (7) | −0.0088 (7) | 0.0033 (6) | −0.0083 (7) |
C11 | 0.0215 (10) | 0.0245 (11) | 0.0243 (10) | −0.0100 (9) | 0.0010 (8) | −0.0105 (9) |
C12 | 0.0239 (11) | 0.0313 (12) | 0.0362 (12) | −0.0134 (10) | 0.0009 (9) | −0.0187 (10) |
C13 | 0.0328 (12) | 0.0319 (13) | 0.0416 (13) | −0.0212 (11) | 0.0157 (10) | −0.0201 (11) |
C14 | 0.0445 (14) | 0.0231 (12) | 0.0248 (11) | −0.0149 (11) | 0.0090 (10) | −0.0067 (9) |
C15 | 0.0299 (11) | 0.0213 (11) | 0.0213 (10) | −0.0073 (9) | 0.0012 (8) | −0.0064 (8) |
C16 | 0.0249 (10) | 0.0304 (12) | 0.0229 (11) | −0.0114 (9) | −0.0011 (8) | −0.0126 (9) |
O21 | 0.0179 (7) | 0.0336 (9) | 0.0242 (7) | −0.0082 (6) | −0.0003 (6) | −0.0125 (6) |
O22 | 0.0260 (8) | 0.0285 (8) | 0.0205 (7) | −0.0068 (7) | −0.0006 (6) | −0.0122 (6) |
C21 | 0.0213 (10) | 0.0195 (10) | 0.0220 (10) | −0.0096 (8) | −0.0016 (8) | −0.0074 (8) |
C22 | 0.0221 (10) | 0.0253 (11) | 0.0258 (11) | −0.0101 (9) | −0.0028 (8) | −0.0111 (9) |
C23 | 0.0203 (10) | 0.0275 (12) | 0.0333 (12) | −0.0129 (9) | −0.0006 (9) | −0.0115 (9) |
C24 | 0.0245 (11) | 0.0286 (12) | 0.0266 (11) | −0.0152 (10) | 0.0032 (8) | −0.0048 (9) |
C25 | 0.0214 (10) | 0.0229 (11) | 0.0221 (10) | −0.0100 (9) | −0.0026 (8) | −0.0021 (8) |
C26 | 0.0206 (10) | 0.0168 (10) | 0.0228 (10) | −0.0072 (8) | −0.0002 (8) | −0.0075 (8) |
Fe2 | 0.02154 (16) | 0.02532 (17) | 0.01983 (15) | −0.00557 (13) | −0.00336 (11) | −0.00890 (12) |
O31 | 0.0497 (11) | 0.0608 (12) | 0.0368 (10) | −0.0366 (10) | 0.0163 (8) | −0.0271 (9) |
O32 | 0.0331 (8) | 0.0430 (10) | 0.0226 (8) | −0.0199 (8) | −0.0020 (6) | −0.0114 (7) |
C31 | 0.0240 (11) | 0.0321 (13) | 0.0335 (12) | −0.0015 (10) | −0.0072 (9) | −0.0168 (10) |
C32 | 0.0571 (16) | 0.0236 (12) | 0.0276 (12) | −0.0083 (12) | −0.0091 (11) | −0.0075 (10) |
C33 | 0.083 (2) | 0.0289 (14) | 0.0350 (14) | −0.0045 (15) | −0.0273 (14) | −0.0073 (11) |
C34 | 0.0558 (18) | 0.0449 (17) | 0.070 (2) | 0.0200 (15) | −0.0444 (16) | −0.0379 (16) |
C35 | 0.0213 (12) | 0.0577 (18) | 0.0694 (19) | −0.0009 (12) | −0.0089 (12) | −0.0446 (16) |
C36 | 0.0186 (10) | 0.0318 (12) | 0.0316 (12) | −0.0066 (9) | 0.0025 (9) | −0.0178 (10) |
O41 | 0.0242 (7) | 0.0386 (9) | 0.0188 (7) | −0.0172 (7) | −0.0001 (6) | −0.0082 (6) |
O42 | 0.0371 (9) | 0.0574 (11) | 0.0152 (7) | −0.0252 (9) | 0.0020 (6) | −0.0097 (7) |
C41 | 0.0206 (10) | 0.0214 (10) | 0.0201 (10) | −0.0070 (8) | −0.0029 (8) | −0.0055 (8) |
C42 | 0.0303 (11) | 0.0340 (13) | 0.0188 (10) | −0.0177 (10) | −0.0052 (8) | −0.0003 (9) |
C43 | 0.0289 (11) | 0.0316 (12) | 0.0220 (10) | −0.0119 (10) | −0.0087 (9) | −0.0038 (9) |
C44 | 0.0182 (10) | 0.0334 (13) | 0.0329 (12) | −0.0079 (9) | −0.0024 (8) | −0.0152 (10) |
C45 | 0.0222 (10) | 0.0301 (12) | 0.0235 (10) | −0.0109 (9) | 0.0037 (8) | −0.0115 (9) |
C46 | 0.0224 (10) | 0.0208 (10) | 0.0177 (9) | −0.0065 (8) | −0.0018 (8) | −0.0061 (8) |
N1 | 0.0251 (9) | 0.0299 (10) | 0.0161 (8) | −0.0152 (8) | −0.0014 (7) | −0.0048 (7) |
C51 | 0.0244 (10) | 0.0261 (11) | 0.0181 (10) | −0.0118 (9) | −0.0020 (8) | −0.0052 (8) |
C52 | 0.0288 (12) | 0.0339 (13) | 0.0280 (12) | −0.0086 (10) | 0.0003 (9) | −0.0092 (10) |
C53 | 0.0413 (14) | 0.0291 (13) | 0.0420 (14) | −0.0066 (11) | −0.0014 (11) | −0.0114 (11) |
C54 | 0.0487 (16) | 0.0257 (13) | 0.0474 (15) | −0.0125 (12) | −0.0060 (12) | −0.0007 (11) |
C55 | 0.0397 (13) | 0.0332 (13) | 0.0345 (13) | −0.0193 (11) | 0.0005 (10) | −0.0019 (10) |
C56 | 0.0304 (11) | 0.0286 (12) | 0.0223 (10) | −0.0128 (10) | 0.0028 (9) | −0.0051 (9) |
C61 | 0.0303 (11) | 0.0254 (11) | 0.0157 (9) | −0.0126 (9) | −0.0034 (8) | −0.0042 (8) |
C62 | 0.0434 (14) | 0.0314 (13) | 0.0388 (13) | −0.0188 (11) | −0.0152 (11) | −0.0024 (10) |
C63 | 0.0640 (18) | 0.0288 (14) | 0.0527 (17) | −0.0166 (13) | −0.0202 (14) | −0.0089 (12) |
C64 | 0.0550 (17) | 0.0294 (14) | 0.0487 (16) | −0.0097 (13) | −0.0164 (13) | −0.0041 (12) |
C65 | 0.0316 (12) | 0.0354 (14) | 0.0409 (14) | −0.0071 (11) | −0.0066 (10) | −0.0091 (11) |
C66 | 0.0282 (11) | 0.0318 (12) | 0.0267 (11) | −0.0133 (10) | −0.0044 (9) | −0.0064 (9) |
N2 | 0.0180 (8) | 0.0197 (9) | 0.0158 (8) | −0.0067 (7) | −0.0016 (6) | −0.0050 (7) |
C71 | 0.0213 (10) | 0.0219 (10) | 0.0156 (9) | −0.0100 (8) | 0.0001 (7) | −0.0023 (8) |
C72 | 0.0259 (10) | 0.0259 (11) | 0.0167 (9) | −0.0103 (9) | −0.0037 (8) | −0.0035 (8) |
C73 | 0.0284 (11) | 0.0313 (12) | 0.0175 (10) | −0.0093 (10) | −0.0024 (8) | 0.0009 (9) |
C74 | 0.0348 (13) | 0.0277 (12) | 0.0278 (12) | −0.0110 (10) | 0.0008 (10) | 0.0019 (9) |
C75 | 0.0367 (13) | 0.0239 (12) | 0.0332 (12) | −0.0155 (10) | 0.0009 (10) | −0.0041 (9) |
C76 | 0.0314 (11) | 0.0261 (12) | 0.0240 (11) | −0.0149 (10) | −0.0023 (9) | −0.0051 (9) |
C81 | 0.0197 (10) | 0.0205 (10) | 0.0159 (9) | −0.0058 (8) | −0.0031 (7) | −0.0053 (8) |
C82 | 0.0285 (11) | 0.0277 (12) | 0.0220 (10) | −0.0122 (10) | −0.0046 (8) | −0.0013 (9) |
C83 | 0.0406 (13) | 0.0377 (14) | 0.0240 (11) | −0.0168 (11) | −0.0089 (10) | 0.0023 (10) |
C84 | 0.0393 (13) | 0.0287 (13) | 0.0348 (13) | −0.0085 (11) | −0.0188 (10) | −0.0011 (10) |
C85 | 0.0251 (11) | 0.0350 (13) | 0.0351 (12) | −0.0087 (10) | −0.0102 (9) | −0.0098 (10) |
C86 | 0.0206 (10) | 0.0309 (12) | 0.0252 (11) | −0.0091 (9) | −0.0026 (8) | −0.0077 (9) |
O91A | 0.123 (7) | 0.148 (10) | 0.125 (6) | −0.047 (7) | −0.009 (6) | −0.086 (8) |
C92A | 0.071 (9) | 0.061 (8) | 0.111 (4) | −0.007 (7) | −0.039 (7) | 0.012 (5) |
C93A | 0.063 (5) | 0.015 (6) | 0.072 (4) | −0.002 (4) | 0.013 (4) | −0.023 (4) |
C94A | 0.068 (2) | 0.034 (5) | 0.047 (5) | −0.021 (3) | −0.017 (4) | 0.010 (5) |
C95A | 0.120 (7) | 0.059 (4) | 0.083 (5) | −0.040 (5) | 0.021 (4) | −0.015 (4) |
O91B | 0.123 (7) | 0.148 (10) | 0.125 (6) | −0.047 (7) | −0.009 (6) | −0.086 (8) |
C92B | 0.071 (9) | 0.061 (8) | 0.111 (4) | −0.007 (7) | −0.039 (7) | 0.012 (5) |
C93B | 0.063 (5) | 0.015 (6) | 0.072 (4) | −0.002 (4) | 0.013 (4) | −0.023 (4) |
C94B | 0.068 (2) | 0.034 (5) | 0.047 (5) | −0.021 (3) | −0.017 (4) | 0.010 (5) |
C95B | 0.120 (7) | 0.059 (4) | 0.083 (5) | −0.040 (5) | 0.021 (4) | −0.015 (4) |
Fe1—C12 | 2.025 (2) | C55—C56 | 1.523 (3) |
Fe1—C25 | 2.030 (2) | C55—H55A | 0.9900 |
Fe1—C11 | 2.030 (2) | C55—H55B | 0.9900 |
Fe1—C24 | 2.041 (2) | C56—H56A | 0.9900 |
Fe1—C21 | 2.046 (2) | C56—H56B | 0.9900 |
Fe1—C13 | 2.048 (2) | C61—C66 | 1.520 (3) |
Fe1—C15 | 2.055 (2) | C61—C62 | 1.524 (3) |
Fe1—C22 | 2.055 (2) | C61—H61 | 1.0000 |
Fe1—C23 | 2.058 (2) | C62—C63 | 1.530 (4) |
Fe1—C14 | 2.067 (2) | C62—H62A | 0.9900 |
O11—C16 | 1.212 (3) | C62—H62B | 0.9900 |
O12—C16 | 1.326 (3) | C63—C64 | 1.522 (4) |
O12—H12 | 0.8400 | C63—H63A | 0.9900 |
C11—C15 | 1.424 (3) | C63—H63B | 0.9900 |
C11—C12 | 1.435 (3) | C64—C65 | 1.522 (4) |
C11—C16 | 1.469 (3) | C64—H64A | 0.9900 |
C12—C13 | 1.420 (3) | C64—H64B | 0.9900 |
C12—H12A | 0.9500 | C65—C66 | 1.523 (3) |
C13—C14 | 1.423 (4) | C65—H65A | 0.9900 |
C13—H13 | 0.9500 | C65—H65B | 0.9900 |
C14—C15 | 1.420 (3) | C66—H66A | 0.9900 |
C14—H14 | 0.9500 | C66—H66B | 0.9900 |
C15—H15 | 0.9500 | N2—C71 | 1.507 (2) |
O21—C26 | 1.276 (2) | N2—C81 | 1.508 (2) |
O22—C26 | 1.248 (2) | N2—H2A | 0.9200 |
C21—C22 | 1.430 (3) | N2—H2B | 0.9200 |
C21—C25 | 1.432 (3) | C71—C76 | 1.520 (3) |
C21—C26 | 1.496 (3) | C71—C72 | 1.526 (3) |
C22—C23 | 1.425 (3) | C71—H71 | 1.0000 |
C22—H22 | 0.9500 | C72—C73 | 1.529 (3) |
C23—C24 | 1.422 (3) | C72—H72A | 0.9900 |
C23—H23 | 0.9500 | C72—H72B | 0.9900 |
C24—C25 | 1.415 (3) | C73—C74 | 1.529 (3) |
C24—H24 | 0.9500 | C73—H73A | 0.9900 |
C25—H25 | 0.9500 | C73—H73B | 0.9900 |
Fe2—C35 | 2.024 (2) | C74—C75 | 1.527 (3) |
Fe2—C34 | 2.024 (3) | C74—H74A | 0.9900 |
Fe2—C41 | 2.026 (2) | C74—H74B | 0.9900 |
Fe2—C42 | 2.030 (2) | C75—C76 | 1.531 (3) |
Fe2—C45 | 2.036 (2) | C75—H75A | 0.9900 |
Fe2—C31 | 2.042 (2) | C75—H75B | 0.9900 |
Fe2—C33 | 2.047 (3) | C76—H76A | 0.9900 |
Fe2—C44 | 2.053 (2) | C76—H76B | 0.9900 |
Fe2—C43 | 2.054 (2) | C81—C82 | 1.524 (3) |
Fe2—C32 | 2.057 (2) | C81—C86 | 1.527 (3) |
O31—C36 | 1.212 (3) | C81—H81 | 1.0000 |
O32—C36 | 1.312 (3) | C82—C83 | 1.524 (3) |
O32—H32 | 0.8400 | C82—H82A | 0.9900 |
C31—C35 | 1.425 (3) | C82—H82B | 0.9900 |
C31—C32 | 1.425 (3) | C83—C84 | 1.522 (3) |
C31—C36 | 1.481 (3) | C83—H83A | 0.9900 |
C32—C33 | 1.418 (4) | C83—H83B | 0.9900 |
C32—H32A | 0.9500 | C84—C85 | 1.519 (3) |
C33—C34 | 1.400 (5) | C84—H84A | 0.9900 |
C33—H33 | 0.9500 | C84—H84B | 0.9900 |
C34—C35 | 1.419 (4) | C85—C86 | 1.528 (3) |
C34—H34 | 0.9500 | C85—H85A | 0.9900 |
C35—H35 | 0.9500 | C85—H85B | 0.9900 |
O41—C46 | 1.271 (2) | C86—H86A | 0.9900 |
O42—C46 | 1.246 (2) | C86—H86B | 0.9900 |
C41—C45 | 1.427 (3) | O91A—C92A | 1.395 (8) |
C41—C42 | 1.435 (3) | O91A—C95A | 1.401 (8) |
C41—C46 | 1.489 (3) | C92A—C93A | 1.464 (9) |
C42—C43 | 1.420 (3) | C92A—H92A | 0.9900 |
C42—H42 | 0.9500 | C92A—H92B | 0.9900 |
C43—C44 | 1.419 (3) | C93A—C94A | 1.499 (8) |
C43—H43 | 0.9500 | C93A—H93A | 0.9900 |
C44—C45 | 1.421 (3) | C93A—H93B | 0.9900 |
C44—H44 | 0.9500 | C94A—C95A | 1.502 (9) |
C45—H45 | 0.9500 | C94A—H94A | 0.9900 |
N1—C51 | 1.498 (3) | C94A—H94B | 0.9900 |
N1—C61 | 1.501 (3) | C95A—H95A | 0.9900 |
N1—H1A | 0.9200 | C95A—H95B | 0.9900 |
N1—H1B | 0.9200 | O91B—C95B | 1.400 (8) |
C51—C52 | 1.520 (3) | O91B—C92B | 1.405 (9) |
C51—C56 | 1.522 (3) | C92B—C93B | 1.465 (9) |
C51—H51 | 1.0000 | C92B—H92C | 0.9900 |
C52—C53 | 1.527 (3) | C92B—H92D | 0.9900 |
C52—H52A | 0.9900 | C93B—C94B | 1.489 (9) |
C52—H52B | 0.9900 | C93B—H93C | 0.9900 |
C53—C54 | 1.525 (4) | C93B—H93D | 0.9900 |
C53—H53A | 0.9900 | C94B—C95B | 1.506 (9) |
C53—H53B | 0.9900 | C94B—H94C | 0.9900 |
C54—C55 | 1.516 (4) | C94B—H94D | 0.9900 |
C54—H54A | 0.9900 | C95B—H95C | 0.9900 |
C54—H54B | 0.9900 | C95B—H95D | 0.9900 |
C16—O12—H12 | 109.5 | C64—C65—C66 | 112.1 (2) |
C15—C11—C12 | 108.09 (18) | C64—C65—H65A | 109.2 |
C15—C11—C16 | 127.77 (19) | C66—C65—H65A | 109.2 |
C12—C11—C16 | 124.1 (2) | C64—C65—H65B | 109.2 |
C13—C12—C11 | 107.5 (2) | C66—C65—H65B | 109.2 |
C13—C12—H12A | 126.3 | H65A—C65—H65B | 107.9 |
C11—C12—H12A | 126.3 | C61—C66—C65 | 108.86 (19) |
C12—C13—C14 | 108.33 (19) | C61—C66—H66A | 109.9 |
C12—C13—H13 | 125.8 | C65—C66—H66A | 109.9 |
C14—C13—H13 | 125.8 | C61—C66—H66B | 109.9 |
C15—C14—C13 | 108.3 (2) | C65—C66—H66B | 109.9 |
C15—C14—H14 | 125.9 | H66A—C66—H66B | 108.3 |
C13—C14—H14 | 125.9 | C71—N2—C81 | 117.77 (15) |
C14—C15—C11 | 107.8 (2) | C71—N2—H2A | 107.9 |
C14—C15—H15 | 126.1 | C81—N2—H2A | 107.9 |
C11—C15—H15 | 126.1 | C71—N2—H2B | 107.9 |
O11—C16—O12 | 123.43 (19) | C81—N2—H2B | 107.9 |
O11—C16—C11 | 123.5 (2) | H2A—N2—H2B | 107.2 |
O12—C16—C11 | 113.07 (18) | N2—C71—C76 | 111.50 (15) |
C22—C21—C25 | 107.30 (17) | N2—C71—C72 | 107.53 (15) |
C22—C21—C26 | 126.06 (18) | C76—C71—C72 | 111.77 (17) |
C25—C21—C26 | 126.64 (18) | N2—C71—H71 | 108.7 |
C23—C22—C21 | 108.47 (18) | C76—C71—H71 | 108.7 |
C23—C22—H22 | 125.8 | C72—C71—H71 | 108.7 |
C21—C22—H22 | 125.8 | C71—C72—C73 | 111.24 (17) |
C24—C23—C22 | 107.37 (18) | C71—C72—H72A | 109.4 |
C24—C23—H23 | 126.3 | C73—C72—H72A | 109.4 |
C22—C23—H23 | 126.3 | C71—C72—H72B | 109.4 |
C25—C24—C23 | 108.87 (18) | C73—C72—H72B | 109.4 |
C25—C24—H24 | 125.6 | H72A—C72—H72B | 108.0 |
C23—C24—H24 | 125.6 | C72—C73—C74 | 111.03 (17) |
C24—C25—C21 | 107.98 (18) | C72—C73—H73A | 109.4 |
C24—C25—H25 | 126.0 | C74—C73—H73A | 109.4 |
C21—C25—H25 | 126.0 | C72—C73—H73B | 109.4 |
O22—C26—O21 | 124.19 (18) | C74—C73—H73B | 109.4 |
O22—C26—C21 | 117.57 (18) | H73A—C73—H73B | 108.0 |
O21—C26—C21 | 118.20 (17) | C75—C74—C73 | 110.10 (19) |
C36—O32—H32 | 109.5 | C75—C74—H74A | 109.6 |
C35—C31—C32 | 108.1 (2) | C73—C74—H74A | 109.6 |
C35—C31—C36 | 124.4 (2) | C75—C74—H74B | 109.6 |
C32—C31—C36 | 127.6 (2) | C73—C74—H74B | 109.6 |
C33—C32—C31 | 107.9 (3) | H74A—C74—H74B | 108.2 |
C33—C32—H32A | 126.1 | C74—C75—C76 | 110.92 (18) |
C31—C32—H32A | 126.1 | C74—C75—H75A | 109.5 |
C34—C33—C32 | 107.8 (3) | C76—C75—H75A | 109.5 |
C34—C33—H33 | 126.1 | C74—C75—H75B | 109.5 |
C32—C33—H33 | 126.1 | C76—C75—H75B | 109.5 |
C33—C34—C35 | 109.4 (2) | H75A—C75—H75B | 108.0 |
C33—C34—H34 | 125.3 | C71—C76—C75 | 110.41 (17) |
C35—C34—H34 | 125.3 | C71—C76—H76A | 109.6 |
C34—C35—C31 | 106.8 (3) | C75—C76—H76A | 109.6 |
C34—C35—H35 | 126.6 | C71—C76—H76B | 109.6 |
C31—C35—H35 | 126.6 | C75—C76—H76B | 109.6 |
O31—C36—O32 | 124.1 (2) | H76A—C76—H76B | 108.1 |
O31—C36—C31 | 123.3 (2) | N2—C81—C82 | 107.62 (16) |
O32—C36—C31 | 112.63 (19) | N2—C81—C86 | 111.78 (15) |
C45—C41—C42 | 107.24 (18) | C82—C81—C86 | 111.40 (17) |
C45—C41—C46 | 125.05 (18) | N2—C81—H81 | 108.7 |
C42—C41—C46 | 127.54 (18) | C82—C81—H81 | 108.7 |
C43—C42—C41 | 107.98 (18) | C86—C81—H81 | 108.7 |
C43—C42—H42 | 126.0 | C81—C82—C83 | 110.88 (18) |
C41—C42—H42 | 126.0 | C81—C82—H82A | 109.5 |
C44—C43—C42 | 108.40 (19) | C83—C82—H82A | 109.5 |
C44—C43—H43 | 125.8 | C81—C82—H82B | 109.5 |
C42—C43—H43 | 125.8 | C83—C82—H82B | 109.5 |
C43—C44—C45 | 107.93 (18) | H82A—C82—H82B | 108.1 |
C43—C44—H44 | 126.0 | C84—C83—C82 | 111.14 (19) |
C45—C44—H44 | 126.0 | C84—C83—H83A | 109.4 |
C44—C45—C41 | 108.43 (18) | C82—C83—H83A | 109.4 |
C44—C45—H45 | 125.8 | C84—C83—H83B | 109.4 |
C41—C45—H45 | 125.8 | C82—C83—H83B | 109.4 |
O42—C46—O41 | 123.09 (19) | H83A—C83—H83B | 108.0 |
O42—C46—C41 | 117.89 (18) | C85—C84—C83 | 110.7 (2) |
O41—C46—C41 | 119.02 (17) | C85—C84—H84A | 109.5 |
C51—N1—C61 | 117.83 (15) | C83—C84—H84A | 109.5 |
C51—N1—H1A | 107.8 | C85—C84—H84B | 109.5 |
C61—N1—H1A | 107.8 | C83—C84—H84B | 109.5 |
C51—N1—H1B | 107.8 | H84A—C84—H84B | 108.1 |
C61—N1—H1B | 107.8 | C84—C85—C86 | 111.87 (19) |
H1A—N1—H1B | 107.2 | C84—C85—H85A | 109.2 |
N1—C51—C52 | 108.53 (16) | C86—C85—H85A | 109.2 |
N1—C51—C56 | 111.25 (16) | C84—C85—H85B | 109.2 |
C52—C51—C56 | 111.32 (18) | C86—C85—H85B | 109.2 |
N1—C51—H51 | 108.6 | H85A—C85—H85B | 107.9 |
C52—C51—H51 | 108.6 | C81—C86—C85 | 110.01 (17) |
C56—C51—H51 | 108.6 | C81—C86—H86A | 109.7 |
C51—C52—C53 | 111.36 (19) | C85—C86—H86A | 109.7 |
C51—C52—H52A | 109.4 | C81—C86—H86B | 109.7 |
C53—C52—H52A | 109.4 | C85—C86—H86B | 109.7 |
C51—C52—H52B | 109.4 | H86A—C86—H86B | 108.2 |
C53—C52—H52B | 109.4 | C92A—O91A—C95A | 105.9 (12) |
H52A—C52—H52B | 108.0 | O91A—C92A—C93A | 121.0 (13) |
C54—C53—C52 | 111.9 (2) | O91A—C92A—H92A | 107.1 |
C54—C53—H53A | 109.2 | C93A—C92A—H92A | 107.1 |
C52—C53—H53A | 109.2 | O91A—C92A—H92B | 107.1 |
C54—C53—H53B | 109.2 | C93A—C92A—H92B | 107.1 |
C52—C53—H53B | 109.2 | H92A—C92A—H92B | 106.8 |
H53A—C53—H53B | 107.9 | C92A—C93A—C94A | 93.0 (13) |
C55—C54—C53 | 111.4 (2) | C92A—C93A—H93A | 113.1 |
C55—C54—H54A | 109.3 | C94A—C93A—H93A | 113.1 |
C53—C54—H54A | 109.3 | C92A—C93A—H93B | 113.1 |
C55—C54—H54B | 109.3 | C94A—C93A—H93B | 113.1 |
C53—C54—H54B | 109.3 | H93A—C93A—H93B | 110.5 |
H54A—C54—H54B | 108.0 | C93A—C94A—C95A | 115.7 (13) |
C54—C55—C56 | 111.7 (2) | C93A—C94A—H94A | 108.3 |
C54—C55—H55A | 109.3 | C95A—C94A—H94A | 108.3 |
C56—C55—H55A | 109.3 | C93A—C94A—H94B | 108.3 |
C54—C55—H55B | 109.3 | C95A—C94A—H94B | 108.3 |
C56—C55—H55B | 109.3 | H94A—C94A—H94B | 107.4 |
H55A—C55—H55B | 107.9 | O91A—C95A—C94A | 103.9 (11) |
C51—C56—C55 | 109.82 (18) | O91A—C95A—H95A | 111.0 |
C51—C56—H56A | 109.7 | C94A—C95A—H95A | 111.0 |
C55—C56—H56A | 109.7 | O91A—C95A—H95B | 111.0 |
C51—C56—H56B | 109.7 | C94A—C95A—H95B | 111.0 |
C55—C56—H56B | 109.7 | H95A—C95A—H95B | 109.0 |
H56A—C56—H56B | 108.2 | C95B—O91B—C92B | 113.4 (13) |
N1—C61—C66 | 113.53 (17) | O91B—C92B—C93B | 97.4 (13) |
N1—C61—C62 | 108.10 (17) | O91B—C92B—H92C | 112.3 |
C66—C61—C62 | 110.52 (18) | C93B—C92B—H92C | 112.3 |
N1—C61—H61 | 108.2 | O91B—C92B—H92D | 112.3 |
C66—C61—H61 | 108.2 | C93B—C92B—H92D | 112.3 |
C62—C61—H61 | 108.2 | H92C—C92B—H92D | 109.9 |
C61—C62—C63 | 109.4 (2) | C92B—C93B—C94B | 117.6 (17) |
C61—C62—H62A | 109.8 | C92B—C93B—H93C | 107.9 |
C63—C62—H62A | 109.8 | C94B—C93B—H93C | 107.9 |
C61—C62—H62B | 109.8 | C92B—C93B—H93D | 107.9 |
C63—C62—H62B | 109.8 | C94B—C93B—H93D | 107.9 |
H62A—C62—H62B | 108.2 | H93C—C93B—H93D | 107.2 |
C64—C63—C62 | 110.9 (2) | C93B—C94B—C95B | 96.3 (13) |
C64—C63—H63A | 109.5 | C93B—C94B—H94C | 112.5 |
C62—C63—H63A | 109.5 | C95B—C94B—H94C | 112.5 |
C64—C63—H63B | 109.5 | C93B—C94B—H94D | 112.5 |
C62—C63—H63B | 109.5 | C95B—C94B—H94D | 112.5 |
H63A—C63—H63B | 108.0 | H94C—C94B—H94D | 110.0 |
C63—C64—C65 | 111.2 (2) | O91B—C95B—C94B | 109.5 (12) |
C63—C64—H64A | 109.4 | O91B—C95B—H95C | 109.8 |
C65—C64—H64A | 109.4 | C94B—C95B—H95C | 109.8 |
C63—C64—H64B | 109.4 | O91B—C95B—H95D | 109.8 |
C65—C64—H64B | 109.4 | C94B—C95B—H95D | 109.8 |
H64A—C64—H64B | 108.0 | H95C—C95B—H95D | 108.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O41 | 0.84 | 1.76 | 2.600 (2) | 174 |
O32—H32···O21i | 0.84 | 1.76 | 2.587 (2) | 170 |
N1—H1A···O42ii | 0.92 | 1.82 | 2.720 (2) | 166 |
N1—H1B···O41 | 0.92 | 1.93 | 2.810 (2) | 161 |
N2—H2A···O21 | 0.92 | 1.91 | 2.822 (2) | 170 |
N2—H2B···O22iii | 0.92 | 1.86 | 2.751 (2) | 162 |
C44—H44···O11 | 0.95 | 2.47 | 3.418 (3) | 173 |
C61—H61···O11 | 1.00 | 2.27 | 3.241 (2) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z; (iii) −x−1, −y+1, −z+1. |
2(C6H21N4)·3(C12H8FeO4) | Z = 2 |
Mr = 1114.64 | F(000) = 1168 |
Triclinic, P1 | Dx = 1.245 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7360 (19) Å | Cell parameters from 7818 reflections |
b = 13.661 (3) Å | θ = 2.6–25.0° |
c = 22.855 (5) Å | µ = 0.78 mm−1 |
α = 97.51 (3)° | T = 150 K |
β = 99.09 (3)° | Block, orange |
γ = 91.11 (3)° | 0.35 × 0.30 × 0.28 mm |
V = 2973.3 (10) Å3 |
Kappa-CCD diffractometer | 10158 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 8024 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ scans, and ω scans with κ offsets | θmax = 25.1°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→11 |
Tmin = 0.772, Tmax = 0.811 | k = −16→16 |
20136 measured reflections | l = −27→26 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0523P)2 + 7.1596P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
10158 reflections | Δρmax = 0.66 e Å−3 |
647 parameters | Δρmin = −0.66 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0130 (10) |
2(C6H21N4)·3(C12H8FeO4) | γ = 91.11 (3)° |
Mr = 1114.64 | V = 2973.3 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.7360 (19) Å | Mo Kα radiation |
b = 13.661 (3) Å | µ = 0.78 mm−1 |
c = 22.855 (5) Å | T = 150 K |
α = 97.51 (3)° | 0.35 × 0.30 × 0.28 mm |
β = 99.09 (3)° |
Kappa-CCD diffractometer | 10158 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 8024 reflections with I > 2σ(I) |
Tmin = 0.772, Tmax = 0.811 | Rint = 0.039 |
20136 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.66 e Å−3 |
10158 reflections | Δρmin = −0.66 e Å−3 |
647 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.30868 (7) | 0.96569 (5) | 0.21472 (3) | 0.0424 (2) | |
O11 | 0.2573 (3) | 1.1392 (2) | 0.09543 (14) | 0.0411 (7) | |
O12 | 0.3769 (3) | 1.0143 (2) | 0.05822 (14) | 0.0390 (7) | |
O21 | 0.6103 (4) | 0.7958 (3) | 0.21831 (17) | 0.0569 (9) | |
O22 | 0.4632 (4) | 0.7464 (3) | 0.27557 (19) | 0.0619 (10) | |
C11 | 0.2310 (4) | 0.9830 (3) | 0.1283 (2) | 0.0357 (10) | |
C12 | 0.1312 (5) | 1.0104 (4) | 0.1665 (2) | 0.0463 (12) | |
H12 | 0.0922 | 1.0734 | 0.1724 | 0.056* | |
C13 | 0.1004 (6) | 0.9273 (4) | 0.1939 (2) | 0.0563 (14) | |
H13 | 0.0370 | 0.9246 | 0.2213 | 0.068* | |
C14 | 0.1810 (6) | 0.8491 (4) | 0.1731 (2) | 0.0545 (14) | |
H14 | 0.1807 | 0.7846 | 0.1844 | 0.065* | |
C15 | 0.2624 (5) | 0.8823 (4) | 0.1326 (2) | 0.0444 (11) | |
H15 | 0.3259 | 0.8446 | 0.1123 | 0.053* | |
C16 | 0.2921 (4) | 1.0518 (3) | 0.0924 (2) | 0.0356 (10) | |
C21 | 0.4772 (5) | 0.9143 (3) | 0.2643 (2) | 0.0407 (11) | |
C22 | 0.5180 (5) | 0.9962 (4) | 0.2370 (2) | 0.0483 (12) | |
H22 | 0.5837 | 0.9945 | 0.2103 | 0.058* | |
C23 | 0.4463 (6) | 1.0795 (4) | 0.2558 (3) | 0.0626 (16) | |
H23 | 0.4536 | 1.1430 | 0.2437 | 0.075* | |
C24 | 0.3624 (7) | 1.0522 (5) | 0.2954 (3) | 0.0700 (18) | |
H24 | 0.3033 | 1.0947 | 0.3154 | 0.084* | |
C25 | 0.3793 (6) | 0.9501 (5) | 0.3014 (2) | 0.0578 (14) | |
H25 | 0.3337 | 0.9130 | 0.3256 | 0.069* | |
C26 | 0.5190 (5) | 0.8115 (4) | 0.2516 (2) | 0.0486 (12) | |
Fe2 | 0.23326 (6) | 0.43954 (5) | 0.28011 (3) | 0.0393 (2) | |
O31 | −0.0187 (3) | 0.4953 (3) | 0.38901 (15) | 0.0491 (8) | |
O32 | 0.1750 (3) | 0.5876 (3) | 0.42889 (14) | 0.0458 (8) | |
O41 | 0.4395 (4) | 0.3952 (3) | 0.43707 (15) | 0.0557 (9) | |
O42 | 0.5632 (3) | 0.4860 (2) | 0.38805 (14) | 0.0433 (8) | |
C31 | 0.1233 (4) | 0.5438 (4) | 0.3231 (2) | 0.0413 (11) | |
C32 | 0.0392 (5) | 0.4966 (4) | 0.2694 (2) | 0.0446 (11) | |
H32 | −0.0469 | 0.4611 | 0.2670 | 0.054* | |
C33 | 0.1067 (5) | 0.5121 (4) | 0.2203 (2) | 0.0505 (13) | |
H33 | 0.0742 | 0.4884 | 0.1794 | 0.061* | |
C34 | 0.2312 (5) | 0.5693 (4) | 0.2435 (2) | 0.0499 (12) | |
H34 | 0.2962 | 0.5911 | 0.2206 | 0.060* | |
C35 | 0.2423 (5) | 0.5885 (4) | 0.3061 (2) | 0.0421 (11) | |
H35 | 0.3163 | 0.6249 | 0.3325 | 0.050* | |
C36 | 0.0910 (5) | 0.5414 (4) | 0.3841 (2) | 0.0430 (11) | |
C41 | 0.3857 (4) | 0.3744 (3) | 0.3332 (2) | 0.0377 (10) | |
C42 | 0.2540 (5) | 0.3200 (4) | 0.3259 (2) | 0.0462 (12) | |
H42 | 0.2049 | 0.3077 | 0.3571 | 0.055* | |
C43 | 0.2112 (5) | 0.2884 (4) | 0.2645 (2) | 0.0501 (13) | |
H43 | 0.1279 | 0.2511 | 0.2474 | 0.060* | |
C44 | 0.3118 (5) | 0.3211 (4) | 0.2325 (2) | 0.0484 (12) | |
H44 | 0.3085 | 0.3095 | 0.1904 | 0.058* | |
C45 | 0.4189 (5) | 0.3744 (4) | 0.2746 (2) | 0.0456 (12) | |
H45 | 0.4997 | 0.4051 | 0.2653 | 0.055* | |
C46 | 0.4684 (5) | 0.4210 (4) | 0.3898 (2) | 0.0417 (11) | |
Fe3 | 0.77350 (6) | 0.23400 (5) | 0.11280 (3) | 0.03136 (18) | |
O51 | 0.5590 (3) | 0.2963 (2) | −0.03067 (13) | 0.0349 (7) | |
O52 | 0.6734 (3) | 0.4374 (2) | 0.01215 (15) | 0.0434 (8) | |
O61 | 0.5337 (3) | 0.4461 (2) | 0.14935 (13) | 0.0371 (7) | |
O62 | 0.7172 (3) | 0.4676 (2) | 0.22235 (13) | 0.0402 (7) | |
C51 | 0.7764 (4) | 0.2901 (3) | 0.03431 (19) | 0.0331 (9) | |
C52 | 0.7968 (4) | 0.1864 (3) | 0.02636 (19) | 0.0338 (10) | |
H52 | 0.7388 | 0.1379 | −0.0005 | 0.041* | |
C53 | 0.9191 (4) | 0.1685 (3) | 0.0656 (2) | 0.0379 (10) | |
H53 | 0.9586 | 0.1061 | 0.0691 | 0.045* | |
C54 | 0.9720 (4) | 0.2603 (3) | 0.0988 (2) | 0.0371 (10) | |
H54 | 1.0521 | 0.2697 | 0.1290 | 0.045* | |
C55 | 0.8850 (4) | 0.3353 (3) | 0.07926 (19) | 0.0339 (9) | |
H55 | 0.8971 | 0.4039 | 0.0936 | 0.041* | |
C56 | 0.6621 (4) | 0.3458 (3) | 0.00297 (19) | 0.0347 (10) | |
C61 | 0.6625 (4) | 0.3061 (3) | 0.17278 (19) | 0.0349 (10) | |
C62 | 0.5766 (4) | 0.2311 (3) | 0.1341 (2) | 0.0346 (10) | |
H62 | 0.4930 | 0.2412 | 0.1084 | 0.041* | |
C63 | 0.6363 (5) | 0.1395 (3) | 0.1405 (2) | 0.0378 (10) | |
H63 | 0.6000 | 0.0771 | 0.1200 | 0.045* | |
C64 | 0.7615 (5) | 0.1567 (4) | 0.1831 (2) | 0.0413 (11) | |
H64 | 0.8232 | 0.1077 | 0.1957 | 0.050* | |
C65 | 0.7772 (4) | 0.2583 (3) | 0.20319 (19) | 0.0361 (10) | |
H65 | 0.8512 | 0.2901 | 0.2320 | 0.043* | |
C66 | 0.6370 (4) | 0.4138 (3) | 0.18199 (19) | 0.0339 (10) | |
N1 | 0.7217 (4) | 0.7140 (3) | 0.43242 (18) | 0.0438 (9) | |
N11 | 0.8165 (4) | 0.5232 (3) | 0.47494 (18) | 0.0471 (10) | |
H11A | 0.7298 | 0.5215 | 0.4530 | 0.071* | |
H11B | 0.8199 | 0.4772 | 0.5005 | 0.071* | |
H11C | 0.8800 | 0.5097 | 0.4500 | 0.071* | |
N12 | 0.4467 (4) | 0.6463 (3) | 0.45247 (18) | 0.0460 (10) | |
H12A | 0.4941 | 0.6045 | 0.4293 | 0.069* | |
H12B | 0.3536 | 0.6330 | 0.4412 | 0.069* | |
H12C | 0.4718 | 0.6379 | 0.4915 | 0.069* | |
N13 | 0.6477 (4) | 0.6083 (3) | 0.30607 (18) | 0.0461 (10) | |
H13A | 0.6267 | 0.5749 | 0.3356 | 0.069* | |
H13B | 0.6670 | 0.5645 | 0.2751 | 0.069* | |
H13C | 0.5739 | 0.6441 | 0.2930 | 0.069* | |
C71 | 0.8577 (5) | 0.7011 (4) | 0.4689 (2) | 0.0515 (13) | |
H71A | 0.8913 | 0.7649 | 0.4932 | 0.062* | |
H71B | 0.9260 | 0.6818 | 0.4421 | 0.062* | |
C72 | 0.8492 (5) | 0.6234 (4) | 0.5098 (2) | 0.0500 (13) | |
H72A | 0.9390 | 0.6230 | 0.5370 | 0.060* | |
H72B | 0.7760 | 0.6400 | 0.5346 | 0.060* | |
C73 | 0.6323 (5) | 0.7768 (4) | 0.4678 (2) | 0.0510 (13) | |
H73A | 0.6517 | 0.8473 | 0.4648 | 0.061* | |
H73B | 0.6543 | 0.7672 | 0.5104 | 0.061* | |
C74 | 0.4803 (5) | 0.7504 (4) | 0.4449 (3) | 0.0546 (13) | |
H74A | 0.4223 | 0.7956 | 0.4670 | 0.066* | |
H74B | 0.4588 | 0.7585 | 0.4020 | 0.066* | |
C75 | 0.7404 (6) | 0.7547 (4) | 0.3780 (2) | 0.0515 (13) | |
H75A | 0.8183 | 0.8048 | 0.3875 | 0.062* | |
H75B | 0.6550 | 0.7881 | 0.3631 | 0.062* | |
C76 | 0.7706 (5) | 0.6756 (4) | 0.3295 (2) | 0.0495 (12) | |
H76A | 0.7986 | 0.7072 | 0.2963 | 0.059* | |
H76B | 0.8492 | 0.6370 | 0.3457 | 0.059* | |
N2 | 0.7918 (3) | 0.7285 (3) | 0.05812 (16) | 0.0330 (8) | |
N21 | 0.6106 (4) | 0.6365 (3) | 0.13459 (16) | 0.0364 (8) | |
H21A | 0.6019 | 0.6898 | 0.1620 | 0.055* | |
H21B | 0.5695 | 0.5821 | 0.1447 | 0.055* | |
H21C | 0.5687 | 0.6479 | 0.0977 | 0.055* | |
N22 | 0.5830 (4) | 0.8869 (3) | 0.03410 (17) | 0.0363 (8) | |
H22A | 0.5919 | 0.9042 | −0.0023 | 0.054* | |
H22B | 0.5195 | 0.9254 | 0.0503 | 0.054* | |
H22C | 0.5538 | 0.8223 | 0.0297 | 0.054* | |
N23 | 0.6267 (3) | 0.6014 (3) | −0.04096 (16) | 0.0330 (8) | |
H23A | 0.6353 | 0.5391 | −0.0311 | 0.050* | |
H23B | 0.5696 | 0.5994 | −0.0767 | 0.050* | |
H23C | 0.5900 | 0.6400 | −0.0122 | 0.050* | |
C81 | 0.8366 (4) | 0.7083 (3) | 0.1200 (2) | 0.0381 (10) | |
H81A | 0.8202 | 0.7667 | 0.1481 | 0.046* | |
H81B | 0.9377 | 0.6972 | 0.1261 | 0.046* | |
C82 | 0.7603 (4) | 0.6197 (4) | 0.1336 (2) | 0.0403 (11) | |
H82A | 0.7692 | 0.5628 | 0.1030 | 0.048* | |
H82B | 0.8039 | 0.6029 | 0.1729 | 0.048* | |
C83 | 0.8248 (4) | 0.8322 (3) | 0.0520 (2) | 0.0352 (10) | |
H83A | 0.8269 | 0.8378 | 0.0094 | 0.042* | |
H83B | 0.9186 | 0.8521 | 0.0748 | 0.042* | |
C84 | 0.7204 (5) | 0.9015 (3) | 0.0744 (2) | 0.0407 (11) | |
H84A | 0.7085 | 0.8898 | 0.1152 | 0.049* | |
H84B | 0.7555 | 0.9707 | 0.0767 | 0.049* | |
C85 | 0.8559 (4) | 0.6593 (3) | 0.01572 (19) | 0.0339 (9) | |
H85A | 0.8681 | 0.5952 | 0.0312 | 0.041* | |
H85B | 0.9491 | 0.6863 | 0.0124 | 0.041* | |
C86 | 0.7666 (4) | 0.6434 (3) | −0.04556 (19) | 0.0345 (10) | |
H86A | 0.7564 | 0.7070 | −0.0618 | 0.041* | |
H86B | 0.8118 | 0.5974 | −0.0732 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0430 (4) | 0.0423 (4) | 0.0419 (4) | 0.0067 (3) | 0.0022 (3) | 0.0111 (3) |
O11 | 0.0368 (17) | 0.0353 (18) | 0.053 (2) | 0.0066 (13) | 0.0065 (14) | 0.0145 (14) |
O12 | 0.0325 (16) | 0.0409 (18) | 0.0456 (18) | 0.0077 (13) | 0.0090 (14) | 0.0091 (14) |
O21 | 0.051 (2) | 0.054 (2) | 0.066 (2) | 0.0088 (17) | 0.0113 (18) | 0.0069 (18) |
O22 | 0.047 (2) | 0.048 (2) | 0.094 (3) | 0.0021 (17) | 0.005 (2) | 0.029 (2) |
C11 | 0.030 (2) | 0.035 (2) | 0.044 (3) | 0.0034 (18) | 0.0034 (18) | 0.0148 (19) |
C12 | 0.035 (3) | 0.054 (3) | 0.051 (3) | 0.007 (2) | 0.004 (2) | 0.013 (2) |
C13 | 0.046 (3) | 0.072 (4) | 0.055 (3) | −0.007 (3) | 0.007 (2) | 0.026 (3) |
C14 | 0.056 (3) | 0.055 (3) | 0.051 (3) | −0.010 (3) | −0.006 (2) | 0.022 (3) |
C15 | 0.049 (3) | 0.039 (3) | 0.042 (3) | 0.003 (2) | −0.003 (2) | 0.008 (2) |
C16 | 0.026 (2) | 0.040 (3) | 0.040 (2) | −0.0004 (18) | −0.0017 (18) | 0.012 (2) |
C21 | 0.042 (3) | 0.039 (3) | 0.041 (3) | 0.004 (2) | 0.000 (2) | 0.011 (2) |
C22 | 0.044 (3) | 0.049 (3) | 0.049 (3) | 0.000 (2) | −0.005 (2) | 0.012 (2) |
C23 | 0.068 (4) | 0.046 (3) | 0.066 (4) | 0.006 (3) | −0.015 (3) | 0.010 (3) |
C24 | 0.073 (4) | 0.075 (4) | 0.053 (4) | 0.033 (3) | −0.008 (3) | −0.006 (3) |
C25 | 0.054 (3) | 0.082 (4) | 0.039 (3) | 0.013 (3) | 0.006 (2) | 0.016 (3) |
C26 | 0.040 (3) | 0.052 (3) | 0.054 (3) | 0.004 (2) | −0.001 (2) | 0.014 (2) |
Fe2 | 0.0290 (3) | 0.0533 (4) | 0.0357 (4) | 0.0034 (3) | 0.0044 (3) | 0.0069 (3) |
O31 | 0.0326 (18) | 0.069 (2) | 0.049 (2) | 0.0017 (16) | 0.0112 (14) | 0.0132 (17) |
O32 | 0.0376 (18) | 0.060 (2) | 0.0402 (18) | 0.0056 (15) | 0.0054 (14) | 0.0090 (16) |
O41 | 0.046 (2) | 0.085 (3) | 0.0369 (19) | −0.0026 (18) | 0.0024 (15) | 0.0175 (18) |
O42 | 0.0349 (17) | 0.053 (2) | 0.0413 (18) | 0.0013 (15) | 0.0020 (14) | 0.0093 (15) |
C31 | 0.028 (2) | 0.054 (3) | 0.042 (3) | 0.010 (2) | 0.0010 (19) | 0.011 (2) |
C32 | 0.029 (2) | 0.053 (3) | 0.052 (3) | 0.006 (2) | 0.002 (2) | 0.012 (2) |
C33 | 0.043 (3) | 0.065 (4) | 0.043 (3) | 0.008 (2) | −0.003 (2) | 0.016 (2) |
C34 | 0.043 (3) | 0.062 (3) | 0.049 (3) | 0.003 (2) | 0.010 (2) | 0.021 (2) |
C35 | 0.033 (2) | 0.050 (3) | 0.044 (3) | 0.005 (2) | 0.005 (2) | 0.013 (2) |
C36 | 0.030 (2) | 0.058 (3) | 0.043 (3) | 0.013 (2) | 0.007 (2) | 0.011 (2) |
C41 | 0.031 (2) | 0.043 (3) | 0.040 (2) | 0.0058 (19) | 0.0070 (18) | 0.004 (2) |
C42 | 0.036 (3) | 0.057 (3) | 0.047 (3) | 0.008 (2) | 0.008 (2) | 0.008 (2) |
C43 | 0.037 (3) | 0.058 (3) | 0.050 (3) | 0.001 (2) | 0.000 (2) | −0.003 (2) |
C44 | 0.040 (3) | 0.062 (3) | 0.041 (3) | 0.011 (2) | 0.005 (2) | 0.001 (2) |
C45 | 0.027 (2) | 0.070 (3) | 0.040 (3) | 0.006 (2) | 0.0077 (19) | 0.005 (2) |
C46 | 0.029 (2) | 0.059 (3) | 0.040 (3) | 0.009 (2) | 0.0083 (19) | 0.012 (2) |
Fe3 | 0.0230 (3) | 0.0364 (4) | 0.0360 (4) | 0.0036 (2) | 0.0045 (2) | 0.0096 (3) |
O51 | 0.0247 (15) | 0.0382 (17) | 0.0419 (17) | 0.0013 (12) | 0.0022 (12) | 0.0102 (13) |
O52 | 0.0391 (18) | 0.0339 (19) | 0.058 (2) | 0.0016 (13) | −0.0009 (15) | 0.0176 (15) |
O61 | 0.0316 (16) | 0.0424 (18) | 0.0371 (17) | 0.0041 (13) | 0.0029 (13) | 0.0074 (13) |
O62 | 0.0326 (16) | 0.0478 (19) | 0.0380 (17) | −0.0018 (14) | 0.0017 (13) | 0.0035 (14) |
C51 | 0.024 (2) | 0.041 (3) | 0.037 (2) | 0.0018 (17) | 0.0066 (17) | 0.0125 (19) |
C52 | 0.027 (2) | 0.039 (3) | 0.037 (2) | 0.0095 (18) | 0.0066 (17) | 0.0067 (19) |
C53 | 0.030 (2) | 0.042 (3) | 0.045 (3) | 0.0105 (19) | 0.0081 (19) | 0.016 (2) |
C54 | 0.025 (2) | 0.048 (3) | 0.041 (3) | 0.0032 (19) | 0.0050 (18) | 0.015 (2) |
C55 | 0.025 (2) | 0.038 (2) | 0.040 (2) | −0.0009 (17) | 0.0048 (17) | 0.0106 (19) |
C56 | 0.025 (2) | 0.045 (3) | 0.037 (2) | 0.0070 (19) | 0.0078 (18) | 0.015 (2) |
C61 | 0.028 (2) | 0.044 (3) | 0.035 (2) | 0.0036 (18) | 0.0072 (18) | 0.0100 (19) |
C62 | 0.026 (2) | 0.040 (3) | 0.041 (2) | −0.0014 (18) | 0.0080 (18) | 0.0103 (19) |
C63 | 0.038 (2) | 0.031 (2) | 0.047 (3) | 0.0035 (19) | 0.010 (2) | 0.0086 (19) |
C64 | 0.036 (2) | 0.044 (3) | 0.048 (3) | 0.009 (2) | 0.009 (2) | 0.017 (2) |
C65 | 0.033 (2) | 0.044 (3) | 0.033 (2) | 0.0052 (19) | 0.0079 (18) | 0.0107 (19) |
C66 | 0.027 (2) | 0.043 (3) | 0.034 (2) | 0.0031 (18) | 0.0101 (18) | 0.0074 (19) |
N1 | 0.039 (2) | 0.048 (2) | 0.046 (2) | 0.0072 (18) | 0.0060 (17) | 0.0104 (18) |
N11 | 0.033 (2) | 0.066 (3) | 0.043 (2) | 0.0044 (19) | 0.0042 (17) | 0.013 (2) |
N12 | 0.037 (2) | 0.055 (3) | 0.046 (2) | 0.0082 (18) | 0.0042 (18) | 0.0120 (19) |
N13 | 0.051 (2) | 0.048 (2) | 0.042 (2) | 0.0085 (19) | 0.0082 (18) | 0.0152 (19) |
C71 | 0.037 (3) | 0.072 (4) | 0.044 (3) | 0.005 (2) | 0.005 (2) | 0.007 (3) |
C72 | 0.041 (3) | 0.068 (4) | 0.042 (3) | 0.008 (2) | 0.004 (2) | 0.015 (2) |
C73 | 0.047 (3) | 0.047 (3) | 0.059 (3) | 0.004 (2) | 0.010 (2) | 0.003 (2) |
C74 | 0.048 (3) | 0.054 (3) | 0.064 (3) | 0.017 (2) | 0.008 (3) | 0.013 (3) |
C75 | 0.051 (3) | 0.054 (3) | 0.050 (3) | 0.002 (2) | 0.005 (2) | 0.013 (2) |
C76 | 0.045 (3) | 0.058 (3) | 0.049 (3) | 0.005 (2) | 0.010 (2) | 0.020 (2) |
N2 | 0.0277 (18) | 0.035 (2) | 0.037 (2) | 0.0030 (15) | 0.0038 (15) | 0.0092 (15) |
N21 | 0.033 (2) | 0.041 (2) | 0.036 (2) | 0.0029 (16) | 0.0051 (15) | 0.0131 (16) |
N22 | 0.0320 (19) | 0.031 (2) | 0.049 (2) | 0.0073 (15) | 0.0097 (16) | 0.0095 (16) |
N23 | 0.0257 (18) | 0.035 (2) | 0.039 (2) | 0.0030 (14) | 0.0011 (15) | 0.0102 (16) |
C81 | 0.030 (2) | 0.048 (3) | 0.036 (2) | 0.0014 (19) | 0.0020 (18) | 0.011 (2) |
C82 | 0.033 (2) | 0.049 (3) | 0.040 (3) | 0.004 (2) | 0.0031 (19) | 0.014 (2) |
C83 | 0.032 (2) | 0.030 (2) | 0.045 (3) | 0.0009 (18) | 0.0041 (19) | 0.0124 (19) |
C84 | 0.037 (2) | 0.040 (3) | 0.045 (3) | 0.004 (2) | 0.003 (2) | 0.008 (2) |
C85 | 0.024 (2) | 0.035 (2) | 0.044 (2) | 0.0030 (17) | 0.0048 (18) | 0.0103 (19) |
C86 | 0.028 (2) | 0.037 (3) | 0.040 (2) | 0.0009 (18) | 0.0076 (18) | 0.0079 (19) |
Fe1—C25 | 2.032 (5) | O62—C66 | 1.254 (5) |
Fe1—C21 | 2.033 (5) | C51—C55 | 1.421 (6) |
Fe1—C14 | 2.035 (5) | C51—C52 | 1.427 (6) |
Fe1—C22 | 2.042 (5) | C51—C56 | 1.501 (6) |
Fe1—C24 | 2.043 (6) | C52—C53 | 1.419 (6) |
Fe1—C15 | 2.044 (5) | C52—H52 | 0.95 |
Fe1—C11 | 2.047 (4) | C53—C54 | 1.419 (7) |
Fe1—C12 | 2.047 (5) | C53—H53 | 0.95 |
Fe1—C13 | 2.050 (5) | C54—C55 | 1.414 (6) |
Fe1—C23 | 2.057 (6) | C54—H54 | 0.95 |
O11—C16 | 1.244 (5) | C55—H55 | 0.95 |
O12—C16 | 1.292 (5) | C61—C62 | 1.424 (6) |
O21—C26 | 1.263 (6) | C61—C65 | 1.435 (6) |
O22—C26 | 1.260 (6) | C61—C66 | 1.491 (6) |
C11—C12 | 1.429 (7) | C62—C63 | 1.405 (6) |
C11—C15 | 1.429 (6) | C62—H62 | 0.95 |
C11—C16 | 1.498 (6) | C63—C64 | 1.430 (6) |
C12—C13 | 1.415 (7) | C63—H63 | 0.95 |
C12—H12 | 0.95 | C64—C65 | 1.402 (7) |
C13—C14 | 1.415 (8) | C64—H64 | 0.95 |
C13—H13 | 0.95 | C65—H65 | 0.95 |
C14—C15 | 1.420 (7) | N1—C75 | 1.463 (6) |
C14—H14 | 0.95 | N1—C71 | 1.475 (6) |
C15—H15 | 0.95 | N1—C73 | 1.489 (6) |
C21—C25 | 1.426 (7) | N11—C72 | 1.493 (7) |
C21—C22 | 1.428 (7) | N11—H11A | 0.91 |
C21—C26 | 1.475 (7) | N11—H11B | 0.91 |
C22—C23 | 1.402 (8) | N11—H11C | 0.91 |
C22—H22 | 0.95 | N12—C74 | 1.491 (7) |
C23—C24 | 1.390 (9) | N12—H12A | 0.91 |
C23—H23 | 0.95 | N12—H12B | 0.91 |
C24—C25 | 1.428 (8) | N12—H12C | 0.91 |
C24—H24 | 0.95 | N13—C76 | 1.480 (6) |
C25—H25 | 0.95 | N13—H13A | 0.91 |
Fe2—C35 | 2.040 (5) | N13—H13B | 0.91 |
Fe2—C31 | 2.040 (5) | N13—H13C | 0.91 |
Fe2—C45 | 2.045 (5) | C71—C72 | 1.514 (7) |
Fe2—C42 | 2.049 (5) | C71—H71A | 0.99 |
Fe2—C43 | 2.050 (5) | C71—H71B | 0.99 |
Fe2—C32 | 2.049 (5) | C72—H72A | 0.99 |
Fe2—C34 | 2.056 (5) | C72—H72B | 0.99 |
Fe2—C41 | 2.057 (4) | C73—C74 | 1.509 (7) |
Fe2—C33 | 2.059 (5) | C73—H73A | 0.99 |
Fe2—C44 | 2.058 (5) | C73—H73B | 0.99 |
O31—C36 | 1.258 (6) | C74—H74A | 0.99 |
O32—C36 | 1.288 (6) | C74—H74B | 0.99 |
O41—C46 | 1.250 (6) | C75—C76 | 1.512 (7) |
O42—C46 | 1.277 (6) | C75—H75A | 0.99 |
C31—C35 | 1.429 (7) | C75—H75B | 0.99 |
C31—C32 | 1.430 (7) | C76—H76A | 0.99 |
C31—C36 | 1.482 (7) | C76—H76B | 0.99 |
C32—C33 | 1.424 (7) | N2—C81 | 1.475 (5) |
C32—H32 | 0.95 | N2—C83 | 1.476 (5) |
C33—C34 | 1.419 (7) | N2—C85 | 1.482 (5) |
C33—H33 | 0.95 | N21—C82 | 1.482 (5) |
C34—C35 | 1.405 (7) | N21—H21A | 0.91 |
C34—H34 | 0.95 | N21—H21B | 0.91 |
C35—H35 | 0.95 | N21—H21C | 0.91 |
C41—C45 | 1.426 (6) | N22—C84 | 1.494 (5) |
C41—C42 | 1.445 (7) | N22—H22A | 0.91 |
C41—C46 | 1.471 (6) | N22—H22B | 0.91 |
C42—C43 | 1.406 (7) | N22—H22C | 0.91 |
C42—H42 | 0.95 | N23—C86 | 1.492 (5) |
C43—C44 | 1.410 (7) | N23—H23A | 0.91 |
C43—H43 | 0.95 | N23—H23B | 0.91 |
C44—C45 | 1.419 (7) | N23—H23C | 0.91 |
C44—H44 | 0.95 | C81—C82 | 1.499 (6) |
C45—H45 | 0.95 | C81—H81A | 0.99 |
Fe3—C54 | 2.041 (4) | C81—H81B | 0.99 |
Fe3—C55 | 2.040 (4) | C82—H82A | 0.99 |
Fe3—C61 | 2.043 (4) | C82—H82B | 0.99 |
Fe3—C65 | 2.043 (4) | C83—C84 | 1.506 (6) |
Fe3—C51 | 2.045 (4) | C83—H83A | 0.99 |
Fe3—C52 | 2.047 (4) | C83—H83B | 0.99 |
Fe3—C64 | 2.052 (5) | C84—H84A | 0.99 |
Fe3—C62 | 2.052 (4) | C84—H84B | 0.99 |
Fe3—C53 | 2.062 (4) | C85—C86 | 1.514 (6) |
Fe3—C63 | 2.065 (5) | C85—H85A | 0.99 |
O51—C56 | 1.285 (5) | C85—H85B | 0.99 |
O52—C56 | 1.240 (5) | C86—H86A | 0.99 |
O61—C66 | 1.277 (5) | C86—H86B | 0.99 |
C12—C11—C15 | 107.9 (4) | C72—N11—H11A | 109.5 |
C12—C11—C16 | 124.2 (4) | C72—N11—H11B | 109.5 |
C15—C11—C16 | 127.8 (4) | H11A—N11—H11B | 109.5 |
C13—C12—C11 | 108.2 (5) | C72—N11—H11C | 109.5 |
C13—C12—H12 | 125.9 | H11A—N11—H11C | 109.5 |
C11—C12—H12 | 125.9 | H11B—N11—H11C | 109.5 |
C12—C13—C14 | 107.7 (5) | C74—N12—H12A | 109.5 |
C12—C13—H13 | 126.2 | C74—N12—H12B | 109.5 |
C14—C13—H13 | 126.2 | H12A—N12—H12B | 109.5 |
C13—C14—C15 | 109.2 (5) | C74—N12—H12C | 109.5 |
C13—C14—H14 | 125.4 | H12A—N12—H12C | 109.5 |
C15—C14—H14 | 125.4 | H12B—N12—H12C | 109.5 |
C14—C15—C11 | 107.0 (5) | C76—N13—H13A | 109.5 |
C14—C15—H15 | 126.5 | C76—N13—H13B | 109.5 |
C11—C15—H15 | 126.5 | H13A—N13—H13B | 109.5 |
O11—C16—O12 | 123.8 (4) | C76—N13—H13C | 109.5 |
O11—C16—C11 | 119.8 (4) | H13A—N13—H13C | 109.5 |
O12—C16—C11 | 116.4 (4) | H13B—N13—H13C | 109.5 |
C25—C21—C22 | 106.4 (5) | N1—C71—C72 | 112.0 (4) |
C25—C21—C26 | 127.3 (5) | N1—C71—H71A | 109.2 |
C22—C21—C26 | 126.1 (5) | C72—C71—H71A | 109.2 |
C23—C22—C21 | 109.5 (5) | N1—C71—H71B | 109.2 |
C23—C22—H22 | 125.3 | C72—C71—H71B | 109.2 |
C21—C22—H22 | 125.3 | H71A—C71—H71B | 107.9 |
C24—C23—C22 | 107.6 (5) | N11—C72—C71 | 111.2 (4) |
C24—C23—H23 | 126.2 | N11—C72—H72A | 109.4 |
C22—C23—H23 | 126.2 | C71—C72—H72A | 109.4 |
C23—C24—C25 | 109.2 (5) | N11—C72—H72B | 109.4 |
C23—C24—H24 | 125.4 | C71—C72—H72B | 109.4 |
C25—C24—H24 | 125.4 | H72A—C72—H72B | 108.0 |
C21—C25—C24 | 107.3 (5) | N1—C73—C74 | 110.5 (4) |
C21—C25—H25 | 126.4 | N1—C73—H73A | 109.5 |
C24—C25—H25 | 126.4 | C74—C73—H73A | 109.5 |
O22—C26—O21 | 125.0 (5) | N1—C73—H73B | 109.5 |
O22—C26—C21 | 117.8 (5) | C74—C73—H73B | 109.5 |
O21—C26—C21 | 117.2 (5) | H73A—C73—H73B | 108.1 |
C35—C31—C32 | 107.2 (4) | N12—C74—C73 | 110.5 (4) |
C35—C31—C36 | 128.2 (4) | N12—C74—H74A | 109.6 |
C32—C31—C36 | 124.6 (4) | C73—C74—H74A | 109.6 |
C33—C32—C31 | 108.2 (4) | N12—C74—H74B | 109.6 |
C33—C32—H32 | 125.9 | C73—C74—H74B | 109.6 |
C31—C32—H32 | 125.9 | H74A—C74—H74B | 108.1 |
C34—C33—C32 | 107.6 (4) | N1—C75—C76 | 112.0 (4) |
C34—C33—H33 | 126.2 | N1—C75—H75A | 109.2 |
C32—C33—H33 | 126.2 | C76—C75—H75A | 109.2 |
C35—C34—C33 | 108.7 (4) | N1—C75—H75B | 109.2 |
C35—C34—H34 | 125.6 | C76—C75—H75B | 109.2 |
C33—C34—H34 | 125.6 | H75A—C75—H75B | 107.9 |
C34—C35—C31 | 108.4 (4) | N13—C76—C75 | 111.6 (4) |
C34—C35—H35 | 125.8 | N13—C76—H76A | 109.3 |
C31—C35—H35 | 125.8 | C75—C76—H76A | 109.3 |
O31—C36—O32 | 123.8 (4) | N13—C76—H76B | 109.3 |
O31—C36—C31 | 117.6 (4) | C75—C76—H76B | 109.3 |
O32—C36—C31 | 118.6 (4) | H76A—C76—H76B | 108.0 |
C45—C41—C42 | 106.3 (4) | C81—N2—C83 | 111.2 (3) |
C45—C41—C46 | 126.9 (4) | C81—N2—C85 | 110.3 (3) |
C42—C41—C46 | 126.8 (4) | C83—N2—C85 | 111.2 (3) |
C43—C42—C41 | 108.1 (4) | C82—N21—H21A | 109.5 |
C43—C42—H42 | 125.9 | C82—N21—H21B | 109.5 |
C41—C42—H42 | 125.9 | H21A—N21—H21B | 109.5 |
C42—C43—C44 | 109.0 (4) | C82—N21—H21C | 109.5 |
C42—C43—H43 | 125.5 | H21A—N21—H21C | 109.5 |
C44—C43—H43 | 125.5 | H21B—N21—H21C | 109.5 |
C43—C44—C45 | 107.6 (4) | C84—N22—H22A | 109.5 |
C43—C44—H44 | 126.2 | C84—N22—H22B | 109.5 |
C45—C44—H44 | 126.2 | H22A—N22—H22B | 109.5 |
C44—C45—C41 | 108.9 (4) | C84—N22—H22C | 109.5 |
C44—C45—H45 | 125.5 | H22A—N22—H22C | 109.5 |
C41—C45—H45 | 125.5 | H22B—N22—H22C | 109.5 |
O41—C46—O42 | 123.9 (4) | C86—N23—H23A | 109.5 |
O41—C46—C41 | 117.4 (4) | C86—N23—H23B | 109.5 |
O42—C46—C41 | 118.7 (4) | H23A—N23—H23B | 109.5 |
C55—C51—C52 | 107.8 (4) | C86—N23—H23C | 109.5 |
C55—C51—C56 | 123.9 (4) | H23A—N23—H23C | 109.5 |
C52—C51—C56 | 128.3 (4) | H23B—N23—H23C | 109.5 |
C53—C52—C51 | 107.8 (4) | N2—C81—C82 | 112.2 (4) |
C53—C52—H52 | 126.1 | N2—C81—H81A | 109.2 |
C51—C52—H52 | 126.1 | C82—C81—H81A | 109.2 |
C54—C53—C52 | 108.0 (4) | N2—C81—H81B | 109.2 |
C54—C53—H53 | 126.0 | C82—C81—H81B | 109.2 |
C52—C53—H53 | 126.0 | H81A—C81—H81B | 107.9 |
C55—C54—C53 | 108.2 (4) | N21—C82—C81 | 112.5 (4) |
C55—C54—H54 | 125.9 | N21—C82—H82A | 109.1 |
C53—C54—H54 | 125.9 | C81—C82—H82A | 109.1 |
C54—C55—C51 | 108.1 (4) | N21—C82—H82B | 109.1 |
C54—C55—H55 | 126.0 | C81—C82—H82B | 109.1 |
C51—C55—H55 | 126.0 | H82A—C82—H82B | 107.8 |
O52—C56—O51 | 124.5 (4) | N2—C83—C84 | 112.2 (4) |
O52—C56—C51 | 117.2 (4) | N2—C83—H83A | 109.2 |
O51—C56—C51 | 118.4 (4) | C84—C83—H83A | 109.2 |
C62—C61—C65 | 107.1 (4) | N2—C83—H83B | 109.2 |
C62—C61—C66 | 127.0 (4) | C84—C83—H83B | 109.2 |
C65—C61—C66 | 125.8 (4) | H83A—C83—H83B | 107.9 |
C63—C62—C61 | 108.5 (4) | N22—C84—C83 | 111.0 (4) |
C63—C62—H62 | 125.8 | N22—C84—H84A | 109.4 |
C61—C62—H62 | 125.8 | C83—C84—H84A | 109.4 |
C62—C63—C64 | 108.0 (4) | N22—C84—H84B | 109.4 |
C62—C63—H63 | 126.0 | C83—C84—H84B | 109.4 |
C64—C63—H63 | 126.0 | H84A—C84—H84B | 108.0 |
C65—C64—C63 | 108.1 (4) | N2—C85—C86 | 111.2 (3) |
C65—C64—H64 | 125.9 | N2—C85—H85A | 109.4 |
C63—C64—H64 | 125.9 | C86—C85—H85A | 109.4 |
C64—C65—C61 | 108.2 (4) | N2—C85—H85B | 109.4 |
C64—C65—H65 | 125.9 | C86—C85—H85B | 109.4 |
C61—C65—H65 | 125.9 | H85A—C85—H85B | 108.0 |
O62—C66—O61 | 123.5 (4) | N23—C86—C85 | 109.6 (3) |
O62—C66—C61 | 118.0 (4) | N23—C86—H86A | 109.7 |
O61—C66—C61 | 118.5 (4) | C85—C86—H86A | 109.7 |
C75—N1—C71 | 110.6 (4) | N23—C86—H86B | 109.7 |
C75—N1—C73 | 111.4 (4) | C85—C86—H86B | 109.7 |
C71—N1—C73 | 110.9 (4) | H86A—C86—H86B | 108.2 |
C15—C11—C12—C13 | −0.4 (5) | C45—C41—C46—O42 | 16.6 (7) |
C16—C11—C12—C13 | −178.6 (4) | C42—C41—C46—O42 | −162.9 (4) |
C11—C12—C13—C14 | 0.3 (6) | C55—C51—C52—C53 | −1.0 (5) |
C12—C13—C14—C15 | 0.0 (6) | C56—C51—C52—C53 | 179.8 (4) |
C13—C14—C15—C11 | −0.2 (6) | C51—C52—C53—C54 | 1.5 (5) |
C12—C11—C15—C14 | 0.3 (5) | C52—C53—C54—C55 | −1.4 (5) |
C16—C11—C15—C14 | 178.5 (4) | C53—C54—C55—C51 | 0.8 (5) |
C12—C11—C16—O11 | 0.8 (7) | C52—C51—C55—C54 | 0.2 (5) |
C15—C11—C16—O11 | −177.1 (4) | C56—C51—C55—C54 | 179.4 (4) |
C12—C11—C16—O12 | −177.2 (4) | C55—C51—C56—O52 | 8.7 (6) |
C15—C11—C16—O12 | 4.9 (7) | C52—C51—C56—O52 | −172.2 (4) |
C25—C21—C22—C23 | −0.9 (6) | C55—C51—C56—O51 | −170.4 (4) |
C26—C21—C22—C23 | 173.9 (5) | C52—C51—C56—O51 | 8.7 (7) |
C21—C22—C23—C24 | 1.1 (6) | C65—C61—C62—C63 | 0.1 (5) |
C22—C23—C24—C25 | −0.8 (6) | C66—C61—C62—C63 | −178.1 (4) |
C22—C21—C25—C24 | 0.4 (6) | C61—C62—C63—C64 | −0.4 (5) |
C26—C21—C25—C24 | −174.3 (5) | C62—C63—C64—C65 | 0.6 (5) |
C23—C24—C25—C21 | 0.2 (6) | C63—C64—C65—C61 | −0.6 (5) |
C25—C21—C26—O22 | 0.2 (8) | C62—C61—C65—C64 | 0.3 (5) |
C22—C21—C26—O22 | −173.5 (5) | C66—C61—C65—C64 | 178.5 (4) |
C25—C21—C26—O21 | −178.5 (5) | C62—C61—C66—O62 | 173.0 (4) |
C22—C21—C26—O21 | 7.8 (7) | C65—C61—C66—O62 | −4.8 (6) |
C35—C31—C32—C33 | 0.2 (5) | C62—C61—C66—O61 | −5.6 (6) |
C36—C31—C32—C33 | −177.7 (4) | C65—C61—C66—O61 | 176.6 (4) |
C31—C32—C33—C34 | −0.5 (6) | C75—N1—C71—C72 | −156.2 (4) |
C32—C33—C34—C35 | 0.6 (6) | C73—N1—C71—C72 | 79.7 (5) |
C33—C34—C35—C31 | −0.5 (6) | N1—C71—C72—N11 | 66.2 (5) |
C32—C31—C35—C34 | 0.1 (5) | C75—N1—C73—C74 | 84.5 (5) |
C36—C31—C35—C34 | 178.0 (5) | C71—N1—C73—C74 | −151.8 (4) |
C35—C31—C36—O31 | −178.1 (4) | N1—C73—C74—N12 | 62.8 (6) |
C32—C31—C36—O31 | −0.5 (7) | C71—N1—C75—C76 | 82.2 (5) |
C35—C31—C36—O32 | 2.9 (7) | C73—N1—C75—C76 | −154.0 (4) |
C32—C31—C36—O32 | −179.5 (4) | N1—C75—C76—N13 | 68.8 (5) |
C45—C41—C42—C43 | 0.2 (5) | C83—N2—C81—C82 | 158.5 (4) |
C46—C41—C42—C43 | 179.9 (5) | C85—N2—C81—C82 | −77.7 (4) |
C41—C42—C43—C44 | 0.0 (6) | N2—C81—C82—N21 | −67.7 (5) |
C42—C43—C44—C45 | −0.3 (6) | C81—N2—C83—C84 | −79.6 (4) |
C43—C44—C45—C41 | 0.4 (6) | C85—N2—C83—C84 | 157.0 (4) |
C42—C41—C45—C44 | −0.4 (5) | N2—C83—C84—N22 | −69.7 (5) |
C46—C41—C45—C44 | 180.0 (4) | C81—N2—C85—C86 | 153.0 (3) |
C45—C41—C46—O41 | −164.5 (5) | C83—N2—C85—C86 | −83.2 (4) |
C42—C41—C46—O41 | 16.0 (7) | N2—C85—C86—N23 | −59.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···O42 | 0.91 | 2.02 | 2.902 (5) | 162 |
N11—H11B···O32i | 0.91 | 1.93 | 2.819 (5) | 164 |
N11—H11C···O31ii | 0.91 | 1.82 | 2.720 (5) | 168 |
N12—H12A···O42 | 0.91 | 1.95 | 2.834 (5) | 163 |
N12—H12B···O32 | 0.91 | 1.80 | 2.699 (5) | 168 |
N12—H12C···O41i | 0.91 | 1.84 | 2.727 (5) | 165 |
N13—H13A···O42 | 0.91 | 1.97 | 2.869 (5) | 170 |
N13—H13B···O62 | 0.91 | 1.80 | 2.704 (5) | 171 |
N13—H13C···O22 | 0.91 | 1.83 | 2.711 (6) | 163 |
N21—H21A···O21 | 0.91 | 1.80 | 2.704 (6) | 172 |
N21—H21B···O61 | 0.91 | 1.90 | 2.770 (5) | 158 |
N21—H21C···O51iii | 0.91 | 2.05 | 2.933 (5) | 162 |
N22—H22A···O12iv | 0.91 | 1.86 | 2.722 (5) | 158 |
N22—H22B···O12 | 0.91 | 1.88 | 2.756 (5) | 161 |
N22—H22C···O51iii | 0.91 | 1.94 | 2.822 (5) | 161 |
N23—H23A···O52 | 0.91 | 1.82 | 2.697 (5) | 161 |
N23—H23B···O61iii | 0.91 | 1.83 | 2.705 (5) | 162 |
N23—H23C···O51iii | 0.91 | 2.02 | 2.887 (5) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z. |
C12H8FeO4·2(C8H12NO) | Z = 3 |
Mr = 548.41 | F(000) = 864 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6828 (4) Å | Cell parameters from 8309 reflections |
b = 13.2119 (4) Å | θ = 2.6–27.5° |
c = 14.3107 (4) Å | µ = 0.62 mm−1 |
α = 64.4870 (14)° | T = 150 K |
β = 68.4460 (12)° | Block, colourless |
γ = 72.2550 (15)° | 0.08 × 0.06 × 0.04 mm |
V = 1981.88 (10) Å3 |
Kappa-CCD diffractometer | 8904 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6112 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 2.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→16 |
Tmin = 0.952, Tmax = 0.976 | k = −15→17 |
24541 measured reflections | l = −16→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.6258P] where P = (Fo2 + 2Fc2)/3 |
8904 reflections | (Δ/σ)max = 0.001 |
508 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
C12H8FeO4·2(C8H12NO) | γ = 72.2550 (15)° |
Mr = 548.41 | V = 1981.88 (10) Å3 |
Triclinic, P1 | Z = 3 |
a = 12.6828 (4) Å | Mo Kα radiation |
b = 13.2119 (4) Å | µ = 0.62 mm−1 |
c = 14.3107 (4) Å | T = 150 K |
α = 64.4870 (14)° | 0.08 × 0.06 × 0.04 mm |
β = 68.4460 (12)° |
Kappa-CCD diffractometer | 8904 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 6112 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.976 | Rint = 0.081 |
24541 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.33 e Å−3 |
8904 reflections | Δρmin = −0.53 e Å−3 |
508 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.5000 | 0.5000 | 0.5000 | 0.03466 (17) | |
O11 | 0.64743 (18) | 0.5780 (2) | 0.19810 (18) | 0.0418 (5) | |
O12 | 0.73846 (18) | 0.4126 (2) | 0.29094 (18) | 0.0423 (5) | |
C11 | 0.5397 (2) | 0.4636 (3) | 0.3658 (3) | 0.0345 (6) | |
C12 | 0.4322 (3) | 0.5411 (3) | 0.3767 (3) | 0.0393 (7) | |
C13 | 0.3556 (3) | 0.4869 (3) | 0.4752 (3) | 0.0436 (8) | |
C14 | 0.4136 (3) | 0.3766 (3) | 0.5268 (3) | 0.0461 (8) | |
C15 | 0.5273 (3) | 0.3622 (3) | 0.4583 (3) | 0.0396 (7) | |
C16 | 0.6489 (2) | 0.4869 (3) | 0.2793 (3) | 0.0351 (7) | |
Fe2 | 0.30134 (4) | 0.21908 (4) | 0.22305 (4) | 0.03451 (15) | |
O21 | 0.01879 (18) | 0.4501 (2) | 0.2086 (2) | 0.0445 (6) | |
O22 | 0.1150 (2) | 0.44640 (19) | 0.04559 (19) | 0.0455 (6) | |
O31 | −0.00173 (18) | 0.15718 (19) | 0.29968 (19) | 0.0403 (5) | |
O32 | 0.07540 (18) | 0.19165 (18) | 0.12346 (18) | 0.0396 (5) | |
C21 | 0.2213 (2) | 0.3844 (2) | 0.1706 (2) | 0.0327 (6) | |
C22 | 0.3330 (3) | 0.3674 (3) | 0.0980 (3) | 0.0399 (7) | |
C23 | 0.4154 (3) | 0.3289 (3) | 0.1567 (3) | 0.0460 (8) | |
C24 | 0.3568 (3) | 0.3208 (3) | 0.2642 (3) | 0.0471 (8) | |
C25 | 0.2368 (3) | 0.3550 (3) | 0.2737 (3) | 0.0372 (7) | |
C26 | 0.1108 (3) | 0.4292 (2) | 0.1394 (3) | 0.0341 (6) | |
C31 | 0.2010 (3) | 0.1177 (2) | 0.2347 (3) | 0.0345 (6) | |
C32 | 0.3085 (3) | 0.1093 (3) | 0.1547 (3) | 0.0407 (7) | |
C33 | 0.3980 (3) | 0.0691 (3) | 0.2051 (3) | 0.0490 (9) | |
C34 | 0.3468 (3) | 0.0533 (3) | 0.3162 (3) | 0.0493 (9) | |
C35 | 0.2256 (3) | 0.0826 (3) | 0.3352 (3) | 0.0405 (7) | |
C36 | 0.0841 (3) | 0.1593 (2) | 0.2171 (3) | 0.0349 (7) | |
O4 | 0.5101 (2) | 0.7786 (2) | 0.1328 (2) | 0.0516 (6) | |
N4 | 0.1317 (2) | 0.6528 (2) | −0.1188 (2) | 0.0368 (6) | |
C41 | 0.4278 (3) | 0.7639 (3) | 0.1014 (3) | 0.0404 (7) | |
C42 | 0.3532 (3) | 0.8596 (3) | 0.0560 (3) | 0.0476 (8) | |
C43 | 0.2681 (3) | 0.8476 (3) | 0.0231 (3) | 0.0448 (8) | |
C44 | 0.2571 (3) | 0.7413 (3) | 0.0343 (3) | 0.0359 (7) | |
C45 | 0.3328 (3) | 0.6467 (3) | 0.0803 (2) | 0.0348 (6) | |
C46 | 0.4173 (3) | 0.6573 (3) | 0.1136 (3) | 0.0380 (7) | |
C47 | 0.1666 (3) | 0.7253 (3) | −0.0015 (3) | 0.0369 (7) | |
C48 | 0.2194 (3) | 0.6877 (3) | −0.0980 (3) | 0.0376 (7) | |
O5 | −0.06574 (19) | 0.50782 (18) | 0.37573 (18) | 0.0388 (5) | |
N5 | 0.1251 (2) | 0.7140 (2) | 0.5740 (2) | 0.0361 (6) | |
C51 | −0.0257 (3) | 0.5924 (2) | 0.3772 (2) | 0.0324 (6) | |
C52 | 0.0846 (3) | 0.6160 (3) | 0.3168 (3) | 0.0355 (7) | |
C53 | 0.1226 (3) | 0.7011 (3) | 0.3218 (3) | 0.0375 (7) | |
C54 | 0.0517 (3) | 0.7647 (2) | 0.3858 (2) | 0.0342 (6) | |
C55 | −0.0593 (3) | 0.7420 (3) | 0.4425 (3) | 0.0352 (6) | |
C56 | −0.0981 (3) | 0.6567 (3) | 0.4389 (3) | 0.0362 (7) | |
C57 | 0.0969 (3) | 0.8515 (3) | 0.3964 (3) | 0.0386 (7) | |
C58 | 0.1795 (3) | 0.7938 (3) | 0.4677 (3) | 0.0380 (7) | |
O6 | −0.1973 (2) | 0.0811 (2) | 0.3588 (2) | 0.0550 (7) | |
N6 | −0.1415 (2) | −0.3574 (2) | 0.1038 (2) | 0.0362 (6) | |
C61 | −0.2004 (3) | 0.0201 (3) | 0.3031 (3) | 0.0416 (7) | |
C62 | −0.3023 (3) | −0.0154 (3) | 0.3276 (3) | 0.0482 (8) | |
C63 | −0.3098 (3) | −0.0774 (3) | 0.2737 (3) | 0.0445 (8) | |
C64 | −0.2157 (3) | −0.1058 (3) | 0.1946 (3) | 0.0387 (7) | |
C65 | −0.1142 (3) | −0.0692 (3) | 0.1723 (3) | 0.0383 (7) | |
C66 | −0.1058 (3) | −0.0066 (3) | 0.2246 (3) | 0.0383 (7) | |
C67 | −0.2212 (3) | −0.1742 (3) | 0.1357 (3) | 0.0415 (7) | |
C68 | −0.1494 (3) | −0.2918 (3) | 0.1689 (3) | 0.0360 (7) | |
H12 | 0.4156 | 0.6155 | 0.3266 | 0.047* | |
H13 | 0.2781 | 0.5187 | 0.5026 | 0.052* | |
H14 | 0.3822 | 0.3224 | 0.5946 | 0.055* | |
H15 | 0.5849 | 0.2962 | 0.4721 | 0.048* | |
H22 | 0.3488 | 0.3798 | 0.0241 | 0.048* | |
H23 | 0.4964 | 0.3114 | 0.1285 | 0.055* | |
H24 | 0.3917 | 0.2967 | 0.3206 | 0.056* | |
H25 | 0.1775 | 0.3577 | 0.3372 | 0.045* | |
H32 | 0.3179 | 0.1276 | 0.0805 | 0.049* | |
H33 | 0.4781 | 0.0552 | 0.1710 | 0.059* | |
H34 | 0.3873 | 0.0273 | 0.3689 | 0.059* | |
H35 | 0.1707 | 0.0795 | 0.4023 | 0.049* | |
H4 | 0.5482 | 0.7148 | 0.1607 | 0.077* | |
H4A | 0.1103 | 0.5881 | −0.0638 | 0.055* | |
H4B | 0.1620 | 0.6397 | −0.1817 | 0.055* | |
H4C | 0.0690 | 0.7094 | −0.1235 | 0.055* | |
H42 | 0.3600 | 0.9330 | 0.0474 | 0.057* | |
H43 | 0.2170 | 0.9132 | −0.0074 | 0.054* | |
H45 | 0.3263 | 0.5732 | 0.0890 | 0.042* | |
H46 | 0.4679 | 0.5916 | 0.1447 | 0.046* | |
H47A | 0.1122 | 0.7979 | −0.0204 | 0.044* | |
H47B | 0.1225 | 0.6675 | 0.0590 | 0.044* | |
H48A | 0.2510 | 0.7511 | −0.1624 | 0.045* | |
H48B | 0.2835 | 0.6229 | −0.0843 | 0.045* | |
H5 | −0.0320 | 0.4977 | 0.3170 | 0.058* | |
H5A | 0.0687 | 0.7542 | 0.6125 | 0.054* | |
H5B | 0.1792 | 0.6723 | 0.6104 | 0.054* | |
H5C | 0.0942 | 0.6666 | 0.5646 | 0.054* | |
H52 | 0.1335 | 0.5740 | 0.2724 | 0.043* | |
H53 | 0.1980 | 0.7164 | 0.2811 | 0.045* | |
H55 | −0.1096 | 0.7860 | 0.4847 | 0.042* | |
H56 | −0.1740 | 0.6423 | 0.4787 | 0.043* | |
H57A | 0.0315 | 0.9017 | 0.4280 | 0.046* | |
H57B | 0.1376 | 0.8994 | 0.3241 | 0.046* | |
H58A | 0.2498 | 0.7517 | 0.4315 | 0.046* | |
H58B | 0.2026 | 0.8527 | 0.4779 | 0.046* | |
H6 | −0.1378 | 0.1109 | 0.3281 | 0.082* | |
H6A | −0.1236 | −0.3131 | 0.0327 | 0.054* | |
H6B | −0.2103 | −0.3792 | 0.1229 | 0.054* | |
H6C | −0.0857 | −0.4203 | 0.1159 | 0.054* | |
H62 | −0.3674 | 0.0027 | 0.3814 | 0.058* | |
H63 | −0.3804 | −0.1011 | 0.2910 | 0.053* | |
H65 | −0.0485 | −0.0880 | 0.1193 | 0.046* | |
H66 | −0.0356 | 0.0181 | 0.2070 | 0.046* | |
H67A | −0.1925 | −0.1344 | 0.0571 | 0.050* | |
H67B | −0.3022 | −0.1810 | 0.1517 | 0.050* | |
H68A | −0.0709 | −0.2845 | 0.1611 | 0.043* | |
H68B | −0.1837 | −0.3342 | 0.2458 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0281 (3) | 0.0440 (4) | 0.0328 (3) | −0.0093 (3) | −0.0053 (3) | −0.0153 (3) |
O11 | 0.0281 (11) | 0.0560 (13) | 0.0377 (13) | −0.0078 (10) | −0.0087 (10) | −0.0138 (11) |
O12 | 0.0286 (11) | 0.0573 (14) | 0.0395 (13) | 0.0041 (10) | −0.0113 (10) | −0.0224 (11) |
C11 | 0.0280 (14) | 0.0436 (16) | 0.0354 (17) | −0.0067 (12) | −0.0078 (13) | −0.0177 (14) |
C12 | 0.0293 (15) | 0.0526 (19) | 0.0396 (18) | −0.0049 (13) | −0.0109 (14) | −0.0202 (15) |
C13 | 0.0273 (15) | 0.064 (2) | 0.047 (2) | −0.0156 (15) | −0.0019 (14) | −0.0283 (17) |
C14 | 0.0436 (19) | 0.053 (2) | 0.045 (2) | −0.0191 (16) | −0.0067 (16) | −0.0180 (16) |
C15 | 0.0348 (16) | 0.0423 (17) | 0.0452 (19) | −0.0072 (13) | −0.0095 (14) | −0.0198 (15) |
C16 | 0.0285 (15) | 0.0496 (18) | 0.0335 (17) | −0.0036 (13) | −0.0095 (13) | −0.0218 (15) |
Fe2 | 0.0273 (2) | 0.0365 (2) | 0.0425 (3) | −0.00190 (17) | −0.0135 (2) | −0.0158 (2) |
O21 | 0.0290 (11) | 0.0578 (14) | 0.0564 (15) | 0.0017 (10) | −0.0135 (11) | −0.0338 (12) |
O22 | 0.0512 (14) | 0.0494 (13) | 0.0388 (13) | −0.0059 (11) | −0.0202 (11) | −0.0139 (11) |
O31 | 0.0336 (11) | 0.0471 (12) | 0.0465 (14) | −0.0077 (9) | −0.0084 (10) | −0.0242 (11) |
O32 | 0.0350 (11) | 0.0447 (12) | 0.0413 (13) | −0.0070 (9) | −0.0133 (10) | −0.0150 (10) |
C21 | 0.0279 (14) | 0.0352 (15) | 0.0358 (16) | −0.0060 (12) | −0.0066 (13) | −0.0149 (13) |
C22 | 0.0341 (16) | 0.0402 (17) | 0.0419 (18) | −0.0074 (13) | −0.0055 (14) | −0.0151 (14) |
C23 | 0.0286 (16) | 0.0453 (18) | 0.064 (2) | −0.0095 (13) | −0.0101 (16) | −0.0202 (17) |
C24 | 0.0402 (18) | 0.052 (2) | 0.061 (2) | −0.0043 (15) | −0.0258 (18) | −0.0242 (18) |
C25 | 0.0359 (16) | 0.0401 (16) | 0.0427 (18) | −0.0058 (13) | −0.0149 (14) | −0.0183 (14) |
C26 | 0.0354 (16) | 0.0312 (14) | 0.0404 (18) | −0.0040 (12) | −0.0142 (14) | −0.0152 (13) |
C31 | 0.0349 (16) | 0.0299 (14) | 0.0411 (17) | −0.0036 (12) | −0.0131 (14) | −0.0141 (13) |
C32 | 0.0361 (17) | 0.0412 (17) | 0.051 (2) | −0.0002 (13) | −0.0169 (15) | −0.0230 (15) |
C33 | 0.0337 (17) | 0.0428 (18) | 0.075 (3) | 0.0051 (14) | −0.0208 (18) | −0.0285 (18) |
C34 | 0.050 (2) | 0.0402 (18) | 0.062 (2) | 0.0020 (15) | −0.0342 (19) | −0.0135 (17) |
C35 | 0.0437 (18) | 0.0348 (16) | 0.0462 (19) | −0.0049 (13) | −0.0197 (16) | −0.0125 (14) |
C36 | 0.0332 (16) | 0.0318 (15) | 0.0446 (19) | −0.0046 (12) | −0.0137 (14) | −0.0165 (13) |
O4 | 0.0463 (14) | 0.0534 (14) | 0.0676 (18) | −0.0097 (11) | −0.0303 (13) | −0.0201 (13) |
N4 | 0.0341 (13) | 0.0436 (14) | 0.0339 (14) | 0.0002 (11) | −0.0120 (11) | −0.0176 (12) |
C41 | 0.0361 (17) | 0.0469 (18) | 0.0448 (19) | −0.0088 (14) | −0.0155 (15) | −0.0177 (15) |
C42 | 0.049 (2) | 0.0347 (16) | 0.066 (2) | −0.0061 (14) | −0.0267 (19) | −0.0157 (16) |
C43 | 0.0461 (19) | 0.0394 (17) | 0.050 (2) | −0.0033 (14) | −0.0257 (17) | −0.0096 (15) |
C44 | 0.0321 (15) | 0.0413 (16) | 0.0349 (17) | −0.0065 (13) | −0.0098 (13) | −0.0137 (13) |
C45 | 0.0322 (15) | 0.0370 (15) | 0.0365 (17) | −0.0057 (12) | −0.0100 (13) | −0.0144 (13) |
C46 | 0.0318 (16) | 0.0425 (17) | 0.0369 (17) | −0.0022 (13) | −0.0098 (14) | −0.0145 (14) |
C47 | 0.0294 (15) | 0.0442 (17) | 0.0392 (17) | −0.0011 (13) | −0.0120 (13) | −0.0182 (14) |
C48 | 0.0301 (15) | 0.0466 (17) | 0.0385 (17) | −0.0034 (13) | −0.0129 (14) | −0.0168 (14) |
O5 | 0.0411 (12) | 0.0435 (12) | 0.0376 (12) | −0.0130 (10) | −0.0107 (10) | −0.0161 (10) |
N5 | 0.0364 (14) | 0.0377 (13) | 0.0371 (15) | −0.0047 (11) | −0.0138 (12) | −0.0141 (11) |
C51 | 0.0334 (15) | 0.0323 (14) | 0.0326 (16) | −0.0057 (12) | −0.0139 (13) | −0.0087 (12) |
C52 | 0.0311 (15) | 0.0407 (16) | 0.0365 (17) | −0.0051 (12) | −0.0082 (13) | −0.0173 (14) |
C53 | 0.0301 (15) | 0.0425 (16) | 0.0397 (18) | −0.0071 (13) | −0.0096 (14) | −0.0141 (14) |
C54 | 0.0358 (16) | 0.0330 (14) | 0.0354 (16) | −0.0044 (12) | −0.0164 (14) | −0.0092 (13) |
C55 | 0.0316 (15) | 0.0390 (16) | 0.0351 (17) | −0.0022 (12) | −0.0102 (13) | −0.0151 (13) |
C56 | 0.0305 (15) | 0.0453 (17) | 0.0340 (17) | −0.0076 (13) | −0.0088 (13) | −0.0145 (14) |
C57 | 0.0416 (17) | 0.0352 (15) | 0.0389 (18) | −0.0075 (13) | −0.0164 (15) | −0.0083 (13) |
C58 | 0.0380 (17) | 0.0405 (16) | 0.0391 (18) | −0.0103 (13) | −0.0131 (14) | −0.0132 (14) |
O6 | 0.0454 (14) | 0.0706 (17) | 0.0645 (17) | −0.0182 (12) | −0.0037 (13) | −0.0424 (15) |
N6 | 0.0285 (12) | 0.0410 (14) | 0.0402 (15) | −0.0056 (10) | −0.0081 (11) | −0.0171 (12) |
C61 | 0.0388 (17) | 0.0432 (17) | 0.049 (2) | −0.0064 (14) | −0.0146 (16) | −0.0202 (15) |
C62 | 0.0349 (17) | 0.053 (2) | 0.059 (2) | −0.0071 (15) | −0.0066 (16) | −0.0284 (18) |
C63 | 0.0306 (16) | 0.0473 (18) | 0.060 (2) | −0.0067 (14) | −0.0139 (16) | −0.0216 (17) |
C64 | 0.0367 (16) | 0.0360 (16) | 0.0474 (19) | −0.0033 (13) | −0.0197 (15) | −0.0139 (14) |
C65 | 0.0362 (16) | 0.0400 (16) | 0.0393 (18) | −0.0060 (13) | −0.0131 (14) | −0.0129 (14) |
C66 | 0.0334 (16) | 0.0406 (16) | 0.0432 (19) | −0.0051 (13) | −0.0139 (14) | −0.0151 (14) |
C67 | 0.0413 (17) | 0.0407 (17) | 0.051 (2) | −0.0023 (14) | −0.0249 (16) | −0.0171 (15) |
C68 | 0.0325 (15) | 0.0425 (16) | 0.0380 (17) | −0.0064 (13) | −0.0138 (14) | −0.0158 (14) |
Fe1—C11i | 2.028 (3) | N4—H4C | 0.91 |
Fe1—C11 | 2.028 (3) | C41—C46 | 1.384 (4) |
Fe1—C12 | 2.038 (3) | C41—C42 | 1.389 (4) |
Fe1—C12i | 2.038 (3) | C42—C43 | 1.398 (4) |
Fe1—C15 | 2.047 (3) | C42—H42 | 0.95 |
Fe1—C15i | 2.047 (3) | C43—C44 | 1.389 (4) |
Fe1—C13i | 2.058 (3) | C43—H43 | 0.95 |
Fe1—C13 | 2.058 (3) | C44—C45 | 1.393 (4) |
Fe1—C14 | 2.062 (3) | C44—C47 | 1.515 (4) |
Fe1—C14i | 2.062 (3) | C45—C46 | 1.386 (4) |
O11—C16 | 1.264 (4) | C45—H45 | 0.95 |
O12—C16 | 1.265 (3) | C46—H46 | 0.95 |
C11—C15 | 1.421 (5) | C47—C48 | 1.521 (4) |
C11—C12 | 1.435 (4) | C47—H47A | 0.99 |
C11—C16 | 1.489 (4) | C47—H47B | 0.99 |
C12—C13 | 1.412 (5) | C48—H48A | 0.99 |
C12—H12 | 0.95 | C48—H48B | 0.99 |
C13—C14 | 1.424 (5) | O5—C51 | 1.371 (3) |
C13—H13 | 0.95 | O5—H5 | 0.84 |
C14—C15 | 1.425 (5) | N5—C58 | 1.480 (4) |
C14—H14 | 0.95 | N5—H5A | 0.91 |
C15—H15 | 0.95 | N5—H5B | 0.91 |
Fe2—C31 | 2.032 (3) | N5—H5C | 0.91 |
Fe2—C22 | 2.033 (3) | C51—C56 | 1.386 (4) |
Fe2—C32 | 2.036 (3) | C51—C52 | 1.395 (4) |
Fe2—C21 | 2.040 (3) | C52—C53 | 1.388 (4) |
Fe2—C35 | 2.044 (3) | C52—H52 | 0.95 |
Fe2—C23 | 2.045 (3) | C53—C54 | 1.396 (4) |
Fe2—C34 | 2.047 (3) | C53—H53 | 0.95 |
Fe2—C25 | 2.051 (3) | C54—C55 | 1.392 (4) |
Fe2—C24 | 2.052 (3) | C54—C57 | 1.510 (4) |
Fe2—C33 | 2.054 (3) | C55—C56 | 1.386 (4) |
O21—C26 | 1.268 (4) | C55—H55 | 0.95 |
O22—C26 | 1.244 (4) | C56—H56 | 0.95 |
O31—C36 | 1.276 (4) | C57—C58 | 1.532 (4) |
O32—C36 | 1.256 (4) | C57—H57A | 0.99 |
C21—C25 | 1.428 (4) | C57—H57B | 0.99 |
C21—C22 | 1.437 (4) | C58—H58A | 0.99 |
C21—C26 | 1.496 (4) | C58—H58B | 0.99 |
C22—C23 | 1.417 (5) | O6—C61 | 1.372 (4) |
C22—H22 | 0.95 | O6—H6 | 0.84 |
C23—C24 | 1.414 (5) | N6—C68 | 1.485 (4) |
C23—H23 | 0.95 | N6—H6A | 0.91 |
C24—C25 | 1.422 (4) | N6—H6B | 0.91 |
C24—H24 | 0.95 | N6—H6C | 0.91 |
C25—H25 | 0.95 | C61—C62 | 1.382 (5) |
C31—C35 | 1.430 (4) | C61—C66 | 1.385 (5) |
C31—C32 | 1.433 (5) | C62—C63 | 1.385 (5) |
C31—C36 | 1.491 (4) | C62—H62 | 0.95 |
C32—C33 | 1.413 (4) | C63—C64 | 1.395 (5) |
C32—H32 | 0.95 | C63—H63 | 0.95 |
C33—C34 | 1.426 (6) | C64—C65 | 1.392 (4) |
C33—H33 | 0.95 | C64—C67 | 1.508 (4) |
C34—C35 | 1.418 (5) | C65—C66 | 1.380 (4) |
C34—H34 | 0.95 | C65—H65 | 0.95 |
C35—H35 | 0.95 | C66—H66 | 0.95 |
O4—C41 | 1.369 (4) | C67—C68 | 1.512 (4) |
O4—H4 | 0.84 | C67—H67A | 0.99 |
N4—C48 | 1.486 (4) | C67—H67B | 0.99 |
N4—H4A | 0.91 | C68—H68A | 0.99 |
N4—H4B | 0.91 | C68—H68B | 0.99 |
C15—C11—C12 | 107.7 (3) | C48—C47—H47B | 109.2 |
C15—C11—C16 | 125.0 (3) | H47A—C47—H47B | 107.9 |
C12—C11—C16 | 127.1 (3) | N4—C48—C47 | 110.7 (2) |
C13—C12—C11 | 107.8 (3) | N4—C48—H48A | 109.5 |
C13—C12—H12 | 126.1 | C47—C48—H48A | 109.5 |
C11—C12—H12 | 126.1 | N4—C48—H48B | 109.5 |
C12—C13—C14 | 108.7 (3) | C47—C48—H48B | 109.5 |
C12—C13—H13 | 125.6 | H48A—C48—H48B | 108.1 |
C14—C13—H13 | 125.6 | C51—O5—H5 | 109.5 |
C13—C14—C15 | 107.5 (3) | C58—N5—H5A | 109.5 |
C13—C14—H14 | 126.2 | C58—N5—H5B | 109.5 |
C15—C14—H14 | 126.2 | H5A—N5—H5B | 109.5 |
C11—C15—C14 | 108.3 (3) | C58—N5—H5C | 109.5 |
C11—C15—H15 | 125.9 | H5A—N5—H5C | 109.5 |
C14—C15—H15 | 125.9 | H5B—N5—H5C | 109.5 |
O11—C16—O12 | 123.5 (3) | O5—C51—C56 | 118.6 (3) |
O11—C16—C11 | 118.9 (3) | O5—C51—C52 | 121.6 (3) |
O12—C16—C11 | 117.5 (3) | C56—C51—C52 | 119.7 (3) |
C25—C21—C22 | 107.7 (3) | C53—C52—C51 | 119.9 (3) |
C25—C21—C26 | 127.6 (3) | C53—C52—H52 | 120.1 |
C22—C21—C26 | 124.6 (3) | C51—C52—H52 | 120.1 |
C23—C22—C21 | 107.6 (3) | C52—C53—C54 | 121.0 (3) |
C23—C22—H22 | 126.2 | C52—C53—H53 | 119.5 |
C21—C22—H22 | 126.2 | C54—C53—H53 | 119.5 |
C24—C23—C22 | 108.5 (3) | C55—C54—C53 | 118.0 (3) |
C24—C23—H23 | 125.7 | C55—C54—C57 | 121.5 (3) |
C22—C23—H23 | 125.7 | C53—C54—C57 | 120.4 (3) |
C23—C24—C25 | 108.4 (3) | C56—C55—C54 | 121.5 (3) |
C23—C24—H24 | 125.8 | C56—C55—H55 | 119.2 |
C25—C24—H24 | 125.8 | C54—C55—H55 | 119.2 |
C24—C25—C21 | 107.7 (3) | C55—C56—C51 | 119.8 (3) |
C24—C25—H25 | 126.1 | C55—C56—H56 | 120.1 |
C21—C25—H25 | 126.1 | C51—C56—H56 | 120.1 |
O22—C26—O21 | 123.6 (3) | C54—C57—C58 | 111.4 (2) |
O22—C26—C21 | 117.8 (3) | C54—C57—H57A | 109.4 |
O21—C26—C21 | 118.6 (3) | C58—C57—H57A | 109.4 |
C35—C31—C32 | 107.8 (3) | C54—C57—H57B | 109.4 |
C35—C31—C36 | 125.5 (3) | C58—C57—H57B | 109.4 |
C32—C31—C36 | 126.6 (3) | H57A—C57—H57B | 108.0 |
C33—C32—C31 | 108.2 (3) | N5—C58—C57 | 111.2 (3) |
C33—C32—H32 | 125.9 | N5—C58—H58A | 109.4 |
C31—C32—H32 | 125.9 | C57—C58—H58A | 109.4 |
C32—C33—C34 | 107.9 (3) | N5—C58—H58B | 109.4 |
C32—C33—H33 | 126.1 | C57—C58—H58B | 109.4 |
C34—C33—H33 | 126.1 | H58A—C58—H58B | 108.0 |
C35—C34—C33 | 108.7 (3) | C61—O6—H6 | 109.5 |
C35—C34—H34 | 125.7 | C68—N6—H6A | 109.5 |
C33—C34—H34 | 125.7 | C68—N6—H6B | 109.5 |
C34—C35—C31 | 107.5 (3) | H6A—N6—H6B | 109.5 |
C34—C35—H35 | 126.2 | C68—N6—H6C | 109.5 |
C31—C35—H35 | 126.2 | H6A—N6—H6C | 109.5 |
O32—C36—O31 | 123.9 (3) | H6B—N6—H6C | 109.5 |
O32—C36—C31 | 118.8 (3) | O6—C61—C62 | 117.9 (3) |
O31—C36—C31 | 117.2 (3) | O6—C61—C66 | 122.3 (3) |
C41—O4—H4 | 109.5 | C62—C61—C66 | 119.8 (3) |
C48—N4—H4A | 109.5 | C61—C62—C63 | 120.1 (3) |
C48—N4—H4B | 109.5 | C61—C62—H62 | 120.0 |
H4A—N4—H4B | 109.5 | C63—C62—H62 | 120.0 |
C48—N4—H4C | 109.5 | C62—C63—C64 | 121.3 (3) |
H4A—N4—H4C | 109.5 | C62—C63—H63 | 119.3 |
H4B—N4—H4C | 109.5 | C64—C63—H63 | 119.3 |
O4—C41—C46 | 122.0 (3) | C65—C64—C63 | 117.1 (3) |
O4—C41—C42 | 118.3 (3) | C65—C64—C67 | 120.4 (3) |
C46—C41—C42 | 119.7 (3) | C63—C64—C67 | 122.4 (3) |
C41—C42—C43 | 119.7 (3) | C66—C65—C64 | 122.1 (3) |
C41—C42—H42 | 120.1 | C66—C65—H65 | 118.9 |
C43—C42—H42 | 120.1 | C64—C65—H65 | 118.9 |
C44—C43—C42 | 121.1 (3) | C65—C66—C61 | 119.5 (3) |
C44—C43—H43 | 119.4 | C65—C66—H66 | 120.3 |
C42—C43—H43 | 119.4 | C61—C66—H66 | 120.3 |
C43—C44—C45 | 117.9 (3) | C64—C67—C68 | 110.7 (2) |
C43—C44—C47 | 122.5 (3) | C64—C67—H67A | 109.5 |
C45—C44—C47 | 119.6 (3) | C68—C67—H67A | 109.5 |
C46—C45—C44 | 121.6 (3) | C64—C67—H67B | 109.5 |
C46—C45—H45 | 119.2 | C68—C67—H67B | 109.5 |
C44—C45—H45 | 119.2 | H67A—C67—H67B | 108.1 |
C41—C46—C45 | 119.9 (3) | N6—C68—C67 | 112.5 (2) |
C41—C46—H46 | 120.1 | N6—C68—H68A | 109.1 |
C45—C46—H46 | 120.1 | C67—C68—H68A | 109.1 |
C44—C47—C48 | 112.1 (2) | N6—C68—H68B | 109.1 |
C44—C47—H47A | 109.2 | C67—C68—H68B | 109.1 |
C48—C47—H47A | 109.2 | H68A—C68—H68B | 107.8 |
C44—C47—H47B | 109.2 | ||
C15—C11—C12—C13 | 0.1 (3) | C42—C43—C44—C45 | 0.6 (5) |
C16—C11—C12—C13 | −174.7 (3) | C42—C43—C44—C47 | −179.4 (3) |
C11—C12—C13—C14 | 0.4 (3) | C43—C44—C45—C46 | −0.4 (5) |
C12—C13—C14—C15 | −0.7 (4) | C47—C44—C45—C46 | 179.6 (3) |
C12—C11—C15—C14 | −0.5 (3) | O4—C41—C46—C45 | −179.8 (3) |
C16—C11—C15—C14 | 174.4 (3) | C42—C41—C46—C45 | 0.2 (5) |
C13—C14—C15—C11 | 0.7 (3) | C44—C45—C46—C41 | 0.0 (5) |
C15—C11—C16—O11 | 176.4 (3) | C43—C44—C47—C48 | 111.5 (4) |
C12—C11—C16—O11 | −9.7 (4) | C45—C44—C47—C48 | −68.6 (4) |
C15—C11—C16—O12 | −2.8 (4) | C44—C47—C48—N4 | 169.8 (3) |
C12—C11—C16—O12 | 171.1 (3) | O5—C51—C52—C53 | −179.0 (3) |
C25—C21—C22—C23 | −0.5 (3) | C56—C51—C52—C53 | 2.2 (4) |
C26—C21—C22—C23 | 177.5 (3) | C51—C52—C53—C54 | −0.6 (5) |
C21—C22—C23—C24 | 0.5 (4) | C52—C53—C54—C55 | −1.4 (4) |
C22—C23—C24—C25 | −0.3 (4) | C52—C53—C54—C57 | 175.8 (3) |
C23—C24—C25—C21 | 0.0 (4) | C53—C54—C55—C56 | 2.0 (4) |
C22—C21—C25—C24 | 0.3 (3) | C57—C54—C55—C56 | −175.3 (3) |
C26—C21—C25—C24 | −177.6 (3) | C54—C55—C56—C51 | −0.4 (4) |
C25—C21—C26—O22 | −177.7 (3) | O5—C51—C56—C55 | 179.4 (3) |
C22—C21—C26—O22 | 4.7 (4) | C52—C51—C56—C55 | −1.7 (4) |
C25—C21—C26—O21 | 3.8 (4) | C55—C54—C57—C58 | 103.4 (3) |
C22—C21—C26—O21 | −173.7 (3) | C53—C54—C57—C58 | −73.7 (4) |
C35—C31—C32—C33 | 0.2 (3) | C54—C57—C58—N5 | −54.5 (4) |
C36—C31—C32—C33 | 178.3 (3) | O6—C61—C62—C63 | −179.9 (3) |
C31—C32—C33—C34 | −0.4 (4) | C66—C61—C62—C63 | 0.0 (5) |
C32—C33—C34—C35 | 0.5 (4) | C61—C62—C63—C64 | 0.2 (5) |
C33—C34—C35—C31 | −0.3 (4) | C62—C63—C64—C65 | 0.1 (5) |
C32—C31—C35—C34 | 0.1 (3) | C62—C63—C64—C67 | 179.3 (3) |
C36—C31—C35—C34 | −178.0 (3) | C63—C64—C65—C66 | −0.7 (5) |
C35—C31—C36—O32 | 177.3 (3) | C67—C64—C65—C66 | −179.9 (3) |
C32—C31—C36—O32 | −0.5 (4) | C64—C65—C66—C61 | 0.9 (5) |
C35—C31—C36—O31 | −4.3 (4) | O6—C61—C66—C65 | 179.3 (3) |
C32—C31—C36—O31 | 178.0 (3) | C62—C61—C66—C65 | −0.5 (5) |
O4—C41—C42—C43 | 180.0 (3) | C65—C64—C67—C68 | 69.2 (4) |
C46—C41—C42—C43 | 0.0 (6) | C63—C64—C67—C68 | −110.0 (3) |
C41—C42—C43—C44 | −0.4 (6) | C64—C67—C68—N6 | −173.4 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O11 | 0.84 | 1.85 | 2.679 (3) | 170 |
N4—H4A···O22 | 0.91 | 1.85 | 2.734 (4) | 162 |
N4—H4B···O12ii | 0.91 | 1.86 | 2.742 (3) | 162 |
N4—H4C···O32iii | 0.91 | 1.90 | 2.801 (3) | 171 |
O5—H5···O21 | 0.84 | 1.75 | 2.577 (3) | 166 |
N5—H5A···O31iv | 0.91 | 1.88 | 2.749 (3) | 158 |
N5—H5B···O12i | 0.91 | 1.83 | 2.726 (3) | 168 |
N5—H5C···O5iv | 0.91 | 2.18 | 2.968 (3) | 145 |
O6—H6···O31 | 0.84 | 1.85 | 2.669 (3) | 164 |
N6—H6A···O32v | 0.91 | 2.11 | 3.009 (4) | 170 |
N6—H6B···O11vi | 0.91 | 1.85 | 2.731 (3) | 164 |
N6—H6C···O21vii | 0.91 | 2.10 | 2.941 (3) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) −x, −y+1, −z+1; (v) −x, −y, −z; (vi) x−1, y−1, z; (vii) x, y−1, z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C12H9FeO4·C2H8N | C12H9FeO4·C6H13N2 | C12H8FeO4·2(C4H10NO)·H2O | C12H10FeO4·C10H8N2 |
Mr | 319.14 | 386.23 | 466.31 | 430.23 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 30.9616 (7), 7.8147 (2), 12.1521 (3) | 7.4666 (3), 10.7846 (5), 11.3184 (6) | 7.4018 (2), 9.2018 (3), 30.3884 (11) | 6.9500 (2), 10.7645 (3), 12.5260 (4) |
α, β, γ (°) | 90, 109.7090 (12), 90 | 104.897 (2), 99.153 (2), 105.238 (2) | 90, 101.0630 (15), 90 | 97.8780 (11), 92.0960 (11), 102.9980 (13) |
V (Å3) | 2768.02 (12) | 824.32 (7) | 2031.29 (11) | 902.27 (5) |
Z | 8 | 2 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 1.10 | 0.94 | 0.79 | 0.87 |
Crystal size (mm) | 0.22 × 0.20 × 0.12 | 0.16 × 0.16 × 0.01 | 0.18 × 0.14 × 0.14 | 0.24 × 0.13 × 0.11 |
Data collection | ||||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.794, 0.879 | 0.864, 0.995 | 0.871, 0.898 | 0.818, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15103, 3166, 2798 | 7460, 2910, 2244 | 10444, 4458, 2882 | 10111, 4096, 3141 |
Rint | 0.037 | 0.051 | 0.047 | 0.039 |
(sin θ/λ)max (Å−1) | 0.650 | 0.596 | 0.649 | 0.650 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.072, 1.03 | 0.040, 0.097, 1.03 | 0.047, 0.100, 1.03 | 0.038, 0.089, 1.03 |
No. of reflections | 3166 | 2910 | 4458 | 4096 |
No. of parameters | 185 | 229 | 279 | 264 |
No. of restraints | 0 | 0 | 2 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.40 | 0.31, −0.33 | 0.39, −0.37 | 0.52, −0.32 |
(V) | (VI) | (VII) | (VIII) | |
Crystal data | ||||
Chemical formula | 2(C8H20N)·C12H8FeO4 | C12H9FeO4·C5H12N | 2(C12H24N)·2(C12H9FeO4)·C4H8O | 2(C6H21N4)·3(C12H8FeO4) |
Mr | 532.53 | 359.20 | 982.83 | 1114.64 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 6.3490 (2), 9.6089 (4), 12.1674 (4) | 5.9880 (3), 19.4750 (12), 13.4340 (9) | 10.3588 (2), 11.9612 (2), 22.7731 (5) | 9.7360 (19), 13.661 (3), 22.855 (5) |
α, β, γ (°) | 98.738 (2), 100.380 (2), 91.2290 (17) | 90, 99.058 (3), 90 | 74.9690 (8), 78.0660 (8), 64.459 (1) | 97.51 (3), 99.09 (3), 91.11 (3) |
V (Å3) | 720.76 (4) | 1547.09 (16) | 2444.18 (8) | 2973.3 (10) |
Z | 1 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.56 | 1.00 | 0.65 | 0.78 |
Crystal size (mm) | 0.26 × 0.08 × 0.06 | 0.30 × 0.15 × 0.12 | 0.26 × 0.20 × 0.08 | 0.35 × 0.30 × 0.28 |
Data collection | ||||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.869, 0.967 | 0.755, 0.890 | 0.849, 0.950 | 0.772, 0.811 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8932, 3268, 2589 | 7828, 2694, 1926 | 27832, 11044, 8558 | 20136, 10158, 8024 |
Rint | 0.052 | 0.068 | 0.041 | 0.039 |
(sin θ/λ)max (Å−1) | 0.651 | 0.596 | 0.649 | 0.597 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.091, 1.07 | 0.045, 0.107, 1.05 | 0.041, 0.102, 1.03 | 0.062, 0.160, 1.09 |
No. of reflections | 3268 | 2694 | 11044 | 10158 |
No. of parameters | 162 | 210 | 603 | 647 |
No. of restraints | 0 | 0 | 10 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.43 | 0.56, −0.66 | 0.57, −0.58 | 0.66, −0.66 |
(IX) | |
Crystal data | |
Chemical formula | C12H8FeO4·2(C8H12NO) |
Mr | 548.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 12.6828 (4), 13.2119 (4), 14.3107 (4) |
α, β, γ (°) | 64.4870 (14), 68.4460 (12), 72.2550 (15) |
V (Å3) | 1981.88 (10) |
Z | 3 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.08 × 0.06 × 0.04 |
Data collection | |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.952, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24541, 8904, 6112 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.150, 1.03 |
No. of reflections | 8904 |
No. of parameters | 508 |
No. of restraints | 0 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.53 |
Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002), ORTEP (Johnson, 1976), PLATON (Spek, 2001), SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O22i | 0.84 | 1.74 | 2.573 (2) | 172 |
N1—H1A···O21ii | 0.92 | 1.85 | 2.752 (2) | 168 |
N1—H1B···O21 | 0.92 | 2.38 | 3.104 (2) | 135 |
N1—H1B···O22 | 0.92 | 1.95 | 2.792 (2) | 152 |
C2—H2B···O12ii | 0.95 | 2.46 | 3.420 (2) | 168 |
C22—H22···O11iii | 0.95 | 2.42 | 3.236 (2) | 143 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N1 | 0.84 | 1.74 | 2.580 (3) | 178 |
N1—H1···O11 | 0.93 | 1.65 | 2.580 (3) | 176 |
O21—H21···N2i | 0.84 | 1.72 | 2.552 (3) | 174 |
N2—H2···O21ii | 0.93 | 1.62 | 2.552 (3) | 177 |
C31—H31B···O22iii | 0.99 | 2.47 | 3.373 (4) | 152 |
C52—H52B···O12iv | 0.99 | 2.33 | 3.262 (4) | 157 |
Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1; (iii) −x, −y, −z; (iv) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N34—H34A···O22i | 0.920 | 1.84 | 2.752 (3) | 170 |
N34—H34B···O11 | 0.920 | 1.93 | 2.763 (3) | 150 |
N44—H44A···O5 | 0.920 | 1.92 | 2.817 (3) | 166 |
N44—H44B···O22 | 0.920 | 1.82 | 2.706 (3) | 162 |
O5—H51···O11 | 0.86 (2) | 1.86 (2) | 2.692 (3) | 160 (3) |
O5—H52···O12ii | 0.85 (2) | 1.86 (2) | 2.715 (3) | 175 (3) |
C45—H45B···O41iii | 0.95 | 2.41 | 3.312 (4) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N31 | 0.84 | 1.83 | 2.674 (2) | 179 |
O21—H21···N41i | 0.84 | 1.79 | 2.629 (2) | 177 |
C46—H46···O12ii | 0.95 | 2.30 | 3.232 (3) | 169 |
Symmetry codes: (i) x−2, y, z+1; (ii) −x+2, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.91 | 1.88 | 2.767 (2) | 165 |
N1—H1B···O2ii | 0.91 | 1.85 | 2.721 (2) | 159 |
N1—H1C···O1 | 0.91 | 1.79 | 2.689 (2) | 168 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O21i | 0.84 | 1.63 | 2.459 (4) | 168 |
O21—H21···O11ii | 0.84 | 1.62 | 2.459 (4) | 176 |
N1—H1A···O12 | 0.92 | 1.89 | 2.746 (4) | 153 |
N1—H1B···O22iii | 0.92 | 2.06 | 2.854 (4) | 144 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O41 | 0.84 | 1.76 | 2.600 (2) | 174 |
O32—H32···O21i | 0.84 | 1.76 | 2.587 (2) | 170 |
N1—H1A···O42ii | 0.92 | 1.82 | 2.720 (2) | 166 |
N1—H1B···O41 | 0.92 | 1.93 | 2.810 (2) | 161 |
N2—H2A···O21 | 0.92 | 1.91 | 2.822 (2) | 170 |
N2—H2B···O22iii | 0.92 | 1.86 | 2.751 (2) | 162 |
C44—H44···O11 | 0.95 | 2.47 | 3.418 (3) | 173 |
C61—H61···O11 | 1.00 | 2.27 | 3.241 (2) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z; (iii) −x−1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···O42 | 0.91 | 2.02 | 2.902 (5) | 162 |
N11—H11B···O32i | 0.91 | 1.93 | 2.819 (5) | 164 |
N11—H11C···O31ii | 0.91 | 1.82 | 2.720 (5) | 168 |
N12—H12A···O42 | 0.91 | 1.95 | 2.834 (5) | 163 |
N12—H12B···O32 | 0.91 | 1.80 | 2.699 (5) | 168 |
N12—H12C···O41i | 0.91 | 1.84 | 2.727 (5) | 165 |
N13—H13A···O42 | 0.91 | 1.97 | 2.869 (5) | 170 |
N13—H13B···O62 | 0.91 | 1.80 | 2.704 (5) | 171 |
N13—H13C···O22 | 0.91 | 1.83 | 2.711 (6) | 163 |
N21—H21A···O21 | 0.91 | 1.80 | 2.704 (6) | 172 |
N21—H21B···O61 | 0.91 | 1.90 | 2.770 (5) | 158 |
N21—H21C···O51iii | 0.91 | 2.05 | 2.933 (5) | 162 |
N22—H22A···O12iv | 0.91 | 1.86 | 2.722 (5) | 158 |
N22—H22B···O12 | 0.91 | 1.88 | 2.756 (5) | 161 |
N22—H22C···O51iii | 0.91 | 1.94 | 2.822 (5) | 161 |
N23—H23A···O52 | 0.91 | 1.82 | 2.697 (5) | 161 |
N23—H23B···O61iii | 0.91 | 1.83 | 2.705 (5) | 162 |
N23—H23C···O51iii | 0.91 | 2.02 | 2.887 (5) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O11 | 0.84 | 1.85 | 2.679 (3) | 170 |
N4—H4A···O22 | 0.91 | 1.85 | 2.734 (4) | 162 |
N4—H4B···O12i | 0.91 | 1.86 | 2.742 (3) | 162 |
N4—H4C···O32ii | 0.91 | 1.90 | 2.801 (3) | 171 |
O5—H5···O21 | 0.84 | 1.75 | 2.577 (3) | 166 |
N5—H5A···O31iii | 0.91 | 1.88 | 2.749 (3) | 158 |
N5—H5B···O12iv | 0.91 | 1.83 | 2.726 (3) | 168 |
N5—H5C···O5iii | 0.91 | 2.18 | 2.968 (3) | 145 |
O6—H6···O31 | 0.84 | 1.85 | 2.669 (3) | 164 |
N6—H6A···O32v | 0.91 | 2.11 | 3.009 (4) | 170 |
N6—H6B···O11vi | 0.91 | 1.85 | 2.731 (3) | 164 |
N6—H6C···O21vii | 0.91 | 2.10 | 2.941 (3) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x, −y, −z; (vi) x−1, y−1, z; (vii) x, y−1, z. |
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