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In the adduct ferrocene-1,1'-diylbis(diphenylmethanol)-1,2-bis(4-pyridyl)ethene (1/1), [Fe(C
18H
15O)
2]·C
12H
10N
2, there is an intramolecular O-H
O hydrogen bond in the ferrocenediol component and a single O-H
N hydrogen bond linking the diol to the diamine, which is disordered over two sets of sites, so forming a finite monomeric adduct. In the adduct ferrocene-1,1'-diylbis(diphenylmethanol)-1,6-diaminohexane (2/1), 2[Fe(C
18H
15O)
2]·C
6H
16N
2, the amine lies across a centre of inversion in space group
P. There is an intramolecular O-H
O hydrogen bond in the ferrocenediol, and the molecular components are linked by O-H
N and N-H
O hydrogen bonds, one of each type, into a
C(13)[
R(12)] chain of rings.
Supporting information
CCDC references: 180123; 180124
For each adduct, equimolar quantities of the ferrocenediol and the appropriate
diamine were separately dissolved in methanol. The component solutions were
mixed and the mixtures were set aside to crystallize, producing analytically
pure (I) and (II). Analyses, compound (I): found C 78.7, H 5.3, N 3.7%;
C48H40FeN2O2 requires C 78.7, H 5.5, N 3.8%; compound (II): found C
76.4, H 6.4, N 2.3%; C78H76Fe2N2O4 requires C 77.0, H 6.3, N 2.3%.
Crystals suitable for single-crystal X-ray diffraction were selected directly
from the analytical samples.
Compounds (I) and (II) both crystallize in the triclinic system; for each, space
group P1 was assumed and subsequently confirmed by the analysis. In
compound (I), the amine component is disordered over two sets of sites; the
minor component was refined with a common isotropic displacement parameter for
all the C and N atoms. All H atoms were treated as riding, with C—H =
0.95–0.99 Å, N—H = 0.91 Å and O—H = 0.84 Å.
For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).
(I) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,2-bis(4'-pyridyl)ethene (1/1)
top
Crystal data top
[Fe(C18H15O)2]·C12H10N2 | Z = 2 |
Mr = 732.67 | F(000) = 768 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6393 (4) Å | Cell parameters from 6061 reflections |
b = 11.4219 (5) Å | θ = 2.6–25.0° |
c = 17.7338 (10) Å | µ = 0.46 mm−1 |
α = 76.7680 (18)° | T = 150 K |
β = 87.4580 (17)° | Block, orange |
γ = 74.064 (3)° | 0.23 × 0.16 × 0.14 mm |
V = 1827.24 (15) Å3 | |
Data collection top
KappaCCD diffractometer | 6460 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4709 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ϕ scans, and ω scans with κ offsets | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = 0→11 |
Tmin = 0.902, Tmax = 0.939 | k = −12→13 |
16969 measured reflections | l = −20→21 |
Refinement top
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0328P)2 + 1.2945P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6460 reflections | Δρmax = 0.55 e Å−3 |
526 parameters | Δρmin = −0.48 e Å−3 |
64 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0044 (10) |
Crystal data top
[Fe(C18H15O)2]·C12H10N2 | γ = 74.064 (3)° |
Mr = 732.67 | V = 1827.24 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6393 (4) Å | Mo Kα radiation |
b = 11.4219 (5) Å | µ = 0.46 mm−1 |
c = 17.7338 (10) Å | T = 150 K |
α = 76.7680 (18)° | 0.23 × 0.16 × 0.14 mm |
β = 87.4580 (17)° | |
Data collection top
KappaCCD diffractometer | 6460 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 4709 reflections with I > 2σ(I) |
Tmin = 0.902, Tmax = 0.939 | Rint = 0.060 |
16969 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 64 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.55 e Å−3 |
6460 reflections | Δρmin = −0.48 e Å−3 |
526 parameters | |
Special details top
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. No transmission coefficients are available from the program (only scale
factors for each frame). The scale factors in the experimental table are
calculated from the 'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.58624 (4) | 0.72258 (4) | 0.81709 (2) | 0.02481 (15) | |
O1 | 0.5773 (2) | 0.4707 (2) | 0.73149 (12) | 0.0306 (5) | |
O2 | 0.3278 (2) | 0.66740 (19) | 0.69347 (11) | 0.0268 (5) | |
C1 | 0.7158 (3) | 0.4598 (3) | 0.76479 (18) | 0.0284 (7) | |
C11 | 0.6947 (3) | 0.5387 (3) | 0.82439 (17) | 0.0265 (7) | |
C12 | 0.5780 (3) | 0.5494 (3) | 0.87751 (17) | 0.0284 (7) | |
C13 | 0.5986 (3) | 0.6217 (3) | 0.92872 (18) | 0.0312 (7) | |
C14 | 0.7287 (3) | 0.6560 (3) | 0.90870 (17) | 0.0302 (7) | |
C15 | 0.7882 (3) | 0.6049 (3) | 0.84492 (17) | 0.0285 (7) | |
C2 | 0.2741 (3) | 0.7655 (3) | 0.73402 (16) | 0.0234 (6) | |
C21 | 0.4007 (3) | 0.8128 (3) | 0.75196 (17) | 0.0240 (7) | |
C22 | 0.4134 (3) | 0.8753 (3) | 0.81122 (18) | 0.0275 (7) | |
C23 | 0.5449 (3) | 0.9119 (3) | 0.80049 (19) | 0.0307 (7) | |
C24 | 0.6126 (3) | 0.8723 (3) | 0.73557 (18) | 0.0314 (7) | |
C25 | 0.5257 (3) | 0.8115 (3) | 0.70495 (17) | 0.0274 (7) | |
C31 | 0.7682 (3) | 0.3196 (3) | 0.80226 (19) | 0.0296 (7) | |
C32 | 0.7704 (3) | 0.2725 (3) | 0.8817 (2) | 0.0357 (8) | |
C33 | 0.7966 (3) | 0.1445 (3) | 0.9128 (2) | 0.0395 (8) | |
C34 | 0.8236 (3) | 0.0621 (3) | 0.8644 (2) | 0.0380 (8) | |
C35 | 0.8293 (3) | 0.1063 (3) | 0.7853 (2) | 0.0397 (8) | |
C36 | 0.8018 (3) | 0.2339 (3) | 0.7548 (2) | 0.0350 (8) | |
C41 | 0.8173 (3) | 0.4988 (3) | 0.70036 (18) | 0.0298 (7) | |
C42 | 0.7654 (3) | 0.5625 (3) | 0.62633 (19) | 0.0345 (8) | |
C43 | 0.8581 (4) | 0.5985 (3) | 0.5686 (2) | 0.0428 (9) | |
C44 | 1.0041 (4) | 0.5698 (3) | 0.5850 (2) | 0.0454 (9) | |
C45 | 1.0576 (4) | 0.5061 (3) | 0.6580 (2) | 0.0424 (9) | |
C46 | 0.9654 (3) | 0.4701 (3) | 0.7156 (2) | 0.0352 (8) | |
C51 | 0.1590 (3) | 0.8709 (3) | 0.68255 (16) | 0.0254 (7) | |
C52 | 0.1677 (3) | 0.9924 (3) | 0.66032 (19) | 0.0359 (8) | |
C53 | 0.0621 (4) | 1.0847 (3) | 0.6122 (2) | 0.0446 (9) | |
C54 | −0.0529 (3) | 1.0549 (3) | 0.58558 (19) | 0.0409 (9) | |
C55 | −0.0630 (3) | 0.9329 (3) | 0.60755 (18) | 0.0366 (8) | |
C56 | 0.0408 (3) | 0.8416 (3) | 0.65594 (17) | 0.0309 (7) | |
C61 | 0.2069 (3) | 0.7107 (3) | 0.80876 (16) | 0.0232 (6) | |
C62 | 0.2243 (3) | 0.5828 (3) | 0.83339 (17) | 0.0266 (7) | |
C63 | 0.1710 (3) | 0.5339 (3) | 0.90432 (18) | 0.0311 (7) | |
C64 | 0.0995 (3) | 0.6124 (3) | 0.95085 (18) | 0.0329 (8) | |
C65 | 0.0752 (3) | 0.7401 (3) | 0.92526 (17) | 0.0307 (7) | |
C66 | 0.1271 (3) | 0.7898 (3) | 0.85407 (17) | 0.0283 (7) | |
N71 | 0.3676 (7) | 0.7351 (6) | 0.53449 (17) | 0.0402 (16) | 0.601 (5) |
C72 | 0.4124 (5) | 0.8394 (5) | 0.5108 (3) | 0.0446 (17) | 0.601 (5) |
C73 | 0.4835 (6) | 0.8597 (5) | 0.4412 (2) | 0.0390 (16) | 0.601 (5) |
C74 | 0.5088 (8) | 0.7760 (5) | 0.3929 (4) | 0.0359 (17) | 0.601 (5) |
C75 | 0.4566 (7) | 0.6713 (6) | 0.4150 (3) | 0.0359 (16) | 0.601 (5) |
C76 | 0.3889 (10) | 0.6565 (8) | 0.4861 (3) | 0.0307 (15) | 0.601 (5) |
C77 | 0.5887 (5) | 0.8000 (4) | 0.31690 (19) | 0.0370 (15) | 0.601 (5) |
N81 | 0.7652 (5) | 0.8689 (6) | 0.0404 (3) | 0.0402 (14) | 0.601 (5) |
C82 | 0.6355 (6) | 0.8445 (7) | 0.0431 (3) | 0.0438 (19) | 0.601 (5) |
C83 | 0.5804 (7) | 0.7959 (7) | 0.11334 (15) | 0.0354 (15) | 0.601 (5) |
C84 | 0.6463 (4) | 0.7841 (6) | 0.1839 (2) | 0.0309 (14) | 0.601 (5) |
C85 | 0.7778 (4) | 0.8131 (5) | 0.1786 (2) | 0.0251 (13) | 0.601 (5) |
C86 | 0.8357 (6) | 0.8535 (7) | 0.10747 (18) | 0.0359 (15) | 0.601 (5) |
C87 | 0.5802 (4) | 0.7417 (4) | 0.26059 (15) | 0.0331 (14) | 0.601 (5) |
N71A | 0.4009 (11) | 0.7434 (11) | 0.5397 (2) | 0.0297 (10)* | 0.399 (5) |
C72A | 0.4710 (8) | 0.8256 (8) | 0.5011 (4) | 0.0297 (10)* | 0.399 (5) |
C73A | 0.5226 (10) | 0.8304 (9) | 0.4264 (4) | 0.0297 (10)* | 0.399 (5) |
C74A | 0.4971 (15) | 0.7452 (12) | 0.3876 (8) | 0.0297 (10)* | 0.399 (5) |
C75A | 0.4243 (14) | 0.6614 (14) | 0.4280 (6) | 0.0297 (10)* | 0.399 (5) |
C76A | 0.3781 (19) | 0.6581 (15) | 0.5036 (6) | 0.0297 (10)* | 0.399 (5) |
C77A | 0.5395 (7) | 0.7481 (7) | 0.3036 (3) | 0.0297 (10)* | 0.399 (5) |
N81A | 0.7340 (10) | 0.8570 (10) | 0.0263 (6) | 0.0297 (10)* | 0.399 (5) |
C82A | 0.6172 (12) | 0.8216 (10) | 0.0569 (5) | 0.0297 (10)* | 0.399 (5) |
C83A | 0.5900 (13) | 0.7940 (12) | 0.1357 (4) | 0.0297 (10)* | 0.399 (5) |
C84A | 0.6884 (9) | 0.8008 (12) | 0.1884 (6) | 0.0297 (10)* | 0.399 (5) |
C85A | 0.8115 (10) | 0.8345 (11) | 0.1590 (4) | 0.0297 (10)* | 0.399 (5) |
C86A | 0.8251 (12) | 0.8656 (12) | 0.0791 (4) | 0.0297 (10)* | 0.399 (5) |
C87A | 0.6540 (7) | 0.7869 (7) | 0.2746 (3) | 0.0297 (10)* | 0.399 (5) |
H1 | 0.5248 | 0.5442 | 0.7270 | 0.046* | |
H2 | 0.3342 | 0.6987 | 0.6462 | 0.040* | |
H12 | 0.4996 | 0.5137 | 0.8782 | 0.034* | |
H13 | 0.5365 | 0.6436 | 0.9694 | 0.037* | |
H14 | 0.7688 | 0.7047 | 0.9337 | 0.036* | |
H15 | 0.8754 | 0.6132 | 0.8200 | 0.034* | |
H22 | 0.3461 | 0.8901 | 0.8511 | 0.033* | |
H23 | 0.5799 | 0.9553 | 0.8318 | 0.037* | |
H24 | 0.7019 | 0.8843 | 0.7154 | 0.038* | |
H25 | 0.5467 | 0.7760 | 0.6609 | 0.033* | |
H32 | 0.7537 | 0.3283 | 0.9156 | 0.043* | |
H33 | 0.7960 | 0.1140 | 0.9673 | 0.047* | |
H34 | 0.8382 | −0.0248 | 0.8855 | 0.046* | |
H35 | 0.8520 | 0.0497 | 0.7520 | 0.048* | |
H36 | 0.8059 | 0.2636 | 0.7004 | 0.042* | |
H42 | 0.6652 | 0.5818 | 0.6148 | 0.041* | |
H43 | 0.8212 | 0.6426 | 0.5182 | 0.051* | |
H44 | 1.0676 | 0.5942 | 0.5458 | 0.055* | |
H45 | 1.1580 | 0.4866 | 0.6691 | 0.051* | |
H46 | 1.0033 | 0.4256 | 0.7657 | 0.042* | |
H52 | 0.2470 | 1.0138 | 0.6780 | 0.043* | |
H53 | 0.0696 | 1.1680 | 0.5979 | 0.054* | |
H54 | −0.1246 | 1.1172 | 0.5525 | 0.049* | |
H55 | −0.1420 | 0.9118 | 0.5892 | 0.044* | |
H56 | 0.0318 | 0.7587 | 0.6711 | 0.037* | |
H62 | 0.2731 | 0.5284 | 0.8016 | 0.032* | |
H63 | 0.1838 | 0.4463 | 0.9208 | 0.037* | |
H64 | 0.0671 | 0.5787 | 1.0003 | 0.039* | |
H65 | 0.0228 | 0.7943 | 0.9564 | 0.037* | |
H66 | 0.1083 | 0.8778 | 0.8363 | 0.034* | |
H72 | 0.3953 | 0.8993 | 0.5419 | 0.053* | 0.601 (5) |
H73 | 0.5157 | 0.9330 | 0.4261 | 0.047* | 0.601 (5) |
H75 | 0.4666 | 0.6130 | 0.3832 | 0.043* | 0.601 (5) |
H76 | 0.3545 | 0.5844 | 0.5020 | 0.037* | 0.601 (5) |
H77 | 0.6456 | 0.8575 | 0.3095 | 0.044* | 0.601 (5) |
H82 | 0.5815 | 0.8607 | −0.0034 | 0.053* | 0.601 (5) |
H83 | 0.4949 | 0.7698 | 0.1132 | 0.042* | 0.601 (5) |
H85 | 0.8293 | 0.8052 | 0.2248 | 0.030* | 0.601 (5) |
H86 | 0.9269 | 0.8708 | 0.1060 | 0.043* | 0.601 (5) |
H87 | 0.5344 | 0.6761 | 0.2685 | 0.040* | 0.601 (5) |
H72A | 0.4864 | 0.8851 | 0.5272 | 0.036* | 0.399 (5) |
H73A | 0.5732 | 0.8895 | 0.4027 | 0.036* | 0.399 (5) |
H75A | 0.4049 | 0.6029 | 0.4024 | 0.036* | 0.399 (5) |
H76A | 0.3315 | 0.5972 | 0.5294 | 0.036* | 0.399 (5) |
H77A | 0.4837 | 0.7221 | 0.2711 | 0.036* | 0.399 (5) |
H82A | 0.5488 | 0.8151 | 0.0222 | 0.036* | 0.399 (5) |
H83A | 0.5049 | 0.7706 | 0.1534 | 0.036* | 0.399 (5) |
H85A | 0.8845 | 0.8362 | 0.1927 | 0.036* | 0.399 (5) |
H86A | 0.9055 | 0.8956 | 0.0600 | 0.036* | 0.399 (5) |
H87A | 0.7148 | 0.8060 | 0.3081 | 0.036* | 0.399 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0211 (2) | 0.0260 (3) | 0.0252 (3) | −0.00347 (17) | 0.00008 (17) | −0.00507 (19) |
O1 | 0.0255 (11) | 0.0264 (12) | 0.0386 (13) | −0.0024 (9) | −0.0046 (9) | −0.0096 (11) |
O2 | 0.0272 (11) | 0.0287 (12) | 0.0231 (11) | −0.0050 (9) | 0.0031 (9) | −0.0067 (9) |
C1 | 0.0222 (15) | 0.0264 (17) | 0.0346 (18) | −0.0021 (12) | −0.0020 (13) | −0.0079 (14) |
C11 | 0.0238 (15) | 0.0230 (17) | 0.0271 (16) | −0.0006 (12) | −0.0025 (12) | −0.0008 (13) |
C12 | 0.0250 (16) | 0.0262 (17) | 0.0303 (17) | −0.0043 (13) | −0.0030 (13) | −0.0014 (14) |
C13 | 0.0285 (17) | 0.0328 (19) | 0.0271 (17) | −0.0008 (14) | −0.0016 (13) | −0.0053 (15) |
C14 | 0.0241 (16) | 0.0335 (19) | 0.0308 (18) | −0.0041 (13) | −0.0051 (13) | −0.0064 (15) |
C15 | 0.0235 (15) | 0.0311 (18) | 0.0279 (17) | −0.0037 (13) | −0.0027 (13) | −0.0046 (14) |
C2 | 0.0216 (14) | 0.0227 (16) | 0.0232 (16) | −0.0021 (12) | 0.0005 (12) | −0.0045 (13) |
C21 | 0.0213 (15) | 0.0206 (16) | 0.0261 (16) | −0.0019 (12) | 0.0002 (12) | −0.0019 (13) |
C22 | 0.0247 (15) | 0.0257 (17) | 0.0294 (17) | −0.0027 (13) | 0.0020 (13) | −0.0063 (14) |
C23 | 0.0277 (16) | 0.0256 (18) | 0.0385 (19) | −0.0059 (13) | −0.0021 (14) | −0.0075 (15) |
C24 | 0.0239 (16) | 0.0307 (18) | 0.0368 (19) | −0.0080 (13) | −0.0003 (14) | −0.0012 (15) |
C25 | 0.0231 (15) | 0.0293 (18) | 0.0246 (16) | −0.0021 (13) | 0.0019 (12) | −0.0022 (14) |
C31 | 0.0206 (15) | 0.0253 (17) | 0.0395 (19) | −0.0016 (12) | −0.0017 (13) | −0.0055 (15) |
C32 | 0.0320 (17) | 0.0283 (19) | 0.043 (2) | −0.0001 (14) | −0.0064 (15) | −0.0086 (16) |
C33 | 0.0340 (18) | 0.033 (2) | 0.043 (2) | −0.0027 (15) | −0.0057 (15) | 0.0017 (17) |
C34 | 0.0259 (17) | 0.0259 (19) | 0.057 (2) | −0.0020 (14) | −0.0038 (15) | −0.0051 (17) |
C35 | 0.0313 (18) | 0.031 (2) | 0.056 (2) | −0.0032 (14) | 0.0010 (16) | −0.0154 (18) |
C36 | 0.0305 (17) | 0.0293 (19) | 0.042 (2) | −0.0041 (14) | −0.0019 (14) | −0.0066 (16) |
C41 | 0.0306 (17) | 0.0243 (17) | 0.0344 (18) | −0.0029 (13) | 0.0020 (14) | −0.0123 (15) |
C42 | 0.0352 (18) | 0.0335 (19) | 0.0367 (19) | −0.0061 (14) | 0.0036 (15) | −0.0160 (16) |
C43 | 0.052 (2) | 0.042 (2) | 0.035 (2) | −0.0144 (17) | 0.0102 (16) | −0.0103 (17) |
C44 | 0.049 (2) | 0.047 (2) | 0.045 (2) | −0.0171 (18) | 0.0199 (18) | −0.0214 (19) |
C45 | 0.0318 (18) | 0.042 (2) | 0.057 (2) | −0.0089 (16) | 0.0106 (17) | −0.0226 (19) |
C46 | 0.0309 (17) | 0.0333 (19) | 0.042 (2) | −0.0051 (14) | 0.0042 (15) | −0.0137 (16) |
C51 | 0.0239 (15) | 0.0292 (18) | 0.0197 (15) | −0.0025 (13) | 0.0012 (12) | −0.0042 (13) |
C52 | 0.0331 (18) | 0.033 (2) | 0.0383 (19) | −0.0090 (14) | −0.0051 (15) | −0.0010 (16) |
C53 | 0.044 (2) | 0.032 (2) | 0.047 (2) | −0.0045 (16) | −0.0053 (17) | 0.0064 (17) |
C54 | 0.0340 (19) | 0.046 (2) | 0.0294 (19) | 0.0043 (16) | −0.0034 (15) | 0.0009 (17) |
C55 | 0.0273 (17) | 0.050 (2) | 0.0281 (18) | −0.0009 (15) | −0.0062 (13) | −0.0114 (16) |
C56 | 0.0291 (16) | 0.0331 (19) | 0.0290 (17) | −0.0049 (14) | 0.0003 (13) | −0.0080 (15) |
C61 | 0.0178 (14) | 0.0286 (17) | 0.0219 (15) | −0.0059 (12) | −0.0016 (12) | −0.0032 (13) |
C62 | 0.0217 (15) | 0.0303 (18) | 0.0261 (16) | −0.0060 (13) | −0.0012 (12) | −0.0036 (14) |
C63 | 0.0240 (15) | 0.0338 (19) | 0.0318 (18) | −0.0104 (14) | −0.0026 (13) | 0.0036 (15) |
C64 | 0.0234 (16) | 0.047 (2) | 0.0248 (17) | −0.0096 (14) | −0.0013 (13) | −0.0007 (16) |
C65 | 0.0210 (15) | 0.040 (2) | 0.0257 (17) | −0.0027 (13) | 0.0026 (12) | −0.0051 (15) |
C66 | 0.0232 (15) | 0.0296 (18) | 0.0283 (17) | −0.0034 (13) | −0.0007 (13) | −0.0034 (14) |
N71 | 0.046 (4) | 0.037 (3) | 0.036 (3) | −0.009 (3) | −0.007 (2) | −0.008 (2) |
C72 | 0.035 (4) | 0.055 (4) | 0.037 (3) | −0.005 (3) | 0.001 (3) | −0.007 (3) |
C73 | 0.046 (4) | 0.028 (4) | 0.045 (4) | −0.009 (3) | −0.001 (3) | −0.011 (3) |
C74 | 0.038 (3) | 0.032 (5) | 0.034 (4) | −0.012 (3) | −0.006 (3) | 0.005 (3) |
C75 | 0.032 (5) | 0.033 (4) | 0.039 (4) | −0.002 (3) | −0.001 (3) | −0.009 (3) |
C76 | 0.037 (3) | 0.036 (3) | 0.018 (4) | −0.007 (3) | 0.003 (3) | −0.007 (3) |
C77 | 0.035 (3) | 0.038 (4) | 0.040 (4) | −0.011 (3) | 0.002 (3) | −0.011 (3) |
N81 | 0.032 (3) | 0.061 (4) | 0.032 (3) | −0.016 (3) | −0.002 (3) | −0.014 (3) |
C82 | 0.044 (4) | 0.076 (6) | 0.028 (4) | −0.040 (4) | 0.023 (3) | −0.019 (4) |
C83 | 0.031 (3) | 0.043 (4) | 0.028 (4) | −0.003 (3) | −0.005 (3) | −0.008 (4) |
C84 | 0.020 (3) | 0.031 (4) | 0.039 (4) | −0.002 (3) | 0.008 (3) | −0.010 (3) |
C85 | 0.014 (3) | 0.033 (3) | 0.019 (3) | 0.000 (2) | 0.008 (2) | 0.005 (2) |
C86 | 0.034 (3) | 0.042 (4) | 0.024 (3) | −0.007 (3) | −0.001 (3) | 0.003 (4) |
C87 | 0.030 (3) | 0.035 (3) | 0.034 (3) | −0.006 (2) | 0.010 (2) | −0.013 (3) |
Geometric parameters (Å, º) top
Fe1—C24 | 2.038 (3) | C54—C55 | 1.387 (5) |
Fe1—C14 | 2.040 (3) | C54—H54 | 0.95 |
Fe1—C13 | 2.040 (3) | C55—C56 | 1.385 (4) |
Fe1—C22 | 2.041 (3) | C55—H55 | 0.95 |
Fe1—C23 | 2.041 (3) | C56—H56 | 0.95 |
Fe1—C12 | 2.044 (3) | C61—C62 | 1.390 (4) |
Fe1—C25 | 2.044 (3) | C61—C66 | 1.396 (4) |
Fe1—C15 | 2.046 (3) | C62—C63 | 1.392 (4) |
Fe1—C11 | 2.050 (3) | C62—H62 | 0.95 |
Fe1—C21 | 2.054 (3) | C63—C64 | 1.382 (4) |
O1—C1 | 1.447 (3) | C63—H63 | 0.95 |
O1—H1 | 0.84 | C64—C65 | 1.381 (5) |
O2—C2 | 1.435 (3) | C64—H64 | 0.95 |
O2—H2 | 0.84 | C65—C66 | 1.392 (4) |
C1—C11 | 1.512 (4) | C65—H65 | 0.95 |
C1—C31 | 1.536 (4) | C66—H66 | 0.95 |
C1—C41 | 1.539 (4) | N71—C72 | 1.3492 (10) |
C11—C15 | 1.431 (4) | N71—C76 | 1.3496 (10) |
C11—C12 | 1.432 (4) | C72—C73 | 1.3882 (10) |
C12—C13 | 1.413 (4) | C72—H72 | 0.95 |
C12—H12 | 0.95 | C73—C74 | 1.3917 (10) |
C13—C14 | 1.420 (4) | C73—H73 | 0.95 |
C13—H13 | 0.95 | C74—C75 | 1.3911 (10) |
C14—C15 | 1.417 (4) | C74—C77 | 1.529 (5) |
C14—H14 | 0.95 | C75—C76 | 1.3895 (10) |
C15—H15 | 0.95 | C75—H75 | 0.95 |
C2—C61 | 1.528 (4) | C76—H76 | 0.95 |
C2—C21 | 1.535 (4) | C77—C87 | 1.3376 (10) |
C2—C51 | 1.538 (4) | C77—H77 | 0.95 |
C21—C22 | 1.426 (4) | N81—C86 | 1.3493 (10) |
C21—C25 | 1.433 (4) | N81—C82 | 1.3497 (10) |
C22—C23 | 1.431 (4) | C82—C83 | 1.3887 (10) |
C22—H22 | 0.95 | C82—H82 | 0.95 |
C23—C24 | 1.402 (4) | C83—C84 | 1.3909 (10) |
C23—H23 | 0.95 | C83—H83 | 0.95 |
C24—C25 | 1.419 (4) | C84—C85 | 1.3899 (10) |
C24—H24 | 0.95 | C84—C87 | 1.511 (4) |
C25—H25 | 0.95 | C85—C86 | 1.3890 (10) |
C31—C32 | 1.388 (4) | C85—H85 | 0.95 |
C31—C36 | 1.396 (4) | C86—H86 | 0.95 |
C32—C33 | 1.394 (5) | C87—H87 | 0.95 |
C32—H32 | 0.95 | N71A—C72A | 1.3496 (10) |
C33—C34 | 1.380 (5) | N71A—C76A | 1.3498 (10) |
C33—H33 | 0.95 | C72A—C73A | 1.3896 (10) |
C34—C35 | 1.382 (5) | C72A—H72A | 0.95 |
C34—H34 | 0.95 | C73A—C74A | 1.3907 (10) |
C35—C36 | 1.387 (5) | C73A—H73A | 0.95 |
C35—H35 | 0.95 | C74A—C75A | 1.3907 (10) |
C36—H36 | 0.95 | C74A—C77A | 1.522 (10) |
C41—C42 | 1.387 (4) | C75A—C76A | 1.3896 (10) |
C41—C46 | 1.398 (4) | C75A—H75A | 0.95 |
C42—C43 | 1.395 (5) | C76A—H76A | 0.95 |
C42—H42 | 0.95 | C77A—C87A | 1.3390 (10) |
C43—C44 | 1.382 (5) | C77A—H77A | 0.95 |
C43—H43 | 0.95 | N81A—C86A | 1.3493 (10) |
C44—C45 | 1.376 (5) | N81A—C82A | 1.3495 (10) |
C44—H44 | 0.95 | C82A—C83A | 1.3896 (10) |
C45—C46 | 1.389 (5) | C82A—H82A | 0.95 |
C45—H45 | 0.95 | C83A—C84A | 1.3904 (10) |
C46—H46 | 0.95 | C83A—H83A | 0.95 |
C51—C52 | 1.377 (4) | C84A—C85A | 1.3900 (10) |
C51—C56 | 1.401 (4) | C84A—C87A | 1.531 (8) |
C52—C53 | 1.397 (4) | C85A—C86A | 1.3894 (10) |
C52—H52 | 0.95 | C85A—H85A | 0.95 |
C53—C54 | 1.376 (5) | C86A—H86A | 0.95 |
C53—H53 | 0.95 | C87A—H87A | 0.95 |
| | | |
C1—O1—H1 | 109.5 | C55—C56—H56 | 119.9 |
C2—O2—H2 | 109.5 | C51—C56—H56 | 119.9 |
O1—C1—C11 | 109.4 (2) | C62—C61—C66 | 118.8 (3) |
O1—C1—C31 | 102.4 (2) | C62—C61—C2 | 121.4 (3) |
C11—C1—C31 | 111.8 (2) | C66—C61—C2 | 119.7 (3) |
O1—C1—C41 | 109.9 (2) | C61—C62—C63 | 120.5 (3) |
C11—C1—C41 | 111.7 (2) | C61—C62—H62 | 119.7 |
C31—C1—C41 | 111.3 (2) | C63—C62—H62 | 119.7 |
C15—C11—C12 | 106.7 (3) | C64—C63—C62 | 120.1 (3) |
C15—C11—C1 | 129.0 (3) | C64—C63—H63 | 119.9 |
C12—C11—C1 | 124.0 (3) | C62—C63—H63 | 119.9 |
C13—C12—C11 | 108.7 (3) | C65—C64—C63 | 119.8 (3) |
C13—C12—H12 | 125.6 | C65—C64—H64 | 120.1 |
C11—C12—H12 | 125.6 | C63—C64—H64 | 120.1 |
C12—C13—C14 | 107.9 (3) | C64—C65—C66 | 120.3 (3) |
C12—C13—H13 | 126.0 | C64—C65—H65 | 119.8 |
C14—C13—H13 | 126.0 | C66—C65—H65 | 119.8 |
C15—C14—C13 | 108.1 (3) | C65—C66—C61 | 120.2 (3) |
C15—C14—H14 | 125.9 | C65—C66—H66 | 119.9 |
C13—C14—H14 | 125.9 | C61—C66—H66 | 119.9 |
C14—C15—C11 | 108.5 (3) | C72—N71—C76 | 117.0 (4) |
C14—C15—H15 | 125.8 | N71—C72—C73 | 120.4 (5) |
C11—C15—H15 | 125.8 | N71—C72—H72 | 119.8 |
O2—C2—C61 | 107.6 (2) | C73—C72—H72 | 119.8 |
O2—C2—C21 | 108.6 (2) | C72—C73—C74 | 122.0 (6) |
C61—C2—C21 | 110.8 (2) | C72—C73—H73 | 119.0 |
O2—C2—C51 | 108.6 (2) | C74—C73—H73 | 119.0 |
C61—C2—C51 | 110.2 (2) | C75—C74—C73 | 117.9 (7) |
C21—C2—C51 | 111.0 (2) | C75—C74—C77 | 121.1 (3) |
C22—C21—C25 | 106.8 (3) | C73—C74—C77 | 120.9 (3) |
C22—C21—C2 | 128.6 (3) | C76—C75—C74 | 116.6 (7) |
C25—C21—C2 | 124.3 (3) | C76—C75—H75 | 121.7 |
C21—C22—C23 | 108.4 (3) | C74—C75—H75 | 121.7 |
C21—C22—H22 | 125.8 | N71—C76—C75 | 126.0 (7) |
C23—C22—H22 | 125.8 | N71—C76—H76 | 117.0 |
C24—C23—C22 | 107.8 (3) | C75—C76—H76 | 117.0 |
C24—C23—H23 | 126.1 | C87—C77—C74 | 121.4 (3) |
C22—C23—H23 | 126.1 | C87—C77—H77 | 119.3 |
C23—C24—C25 | 108.7 (3) | C74—C77—H77 | 119.3 |
C23—C24—H24 | 125.7 | C86—N81—C82 | 118.8 (6) |
C25—C24—H24 | 125.7 | N81—C82—C83 | 120.7 (6) |
C24—C25—C21 | 108.2 (3) | N81—C82—H82 | 119.7 |
C24—C25—H25 | 125.9 | C83—C82—H82 | 119.7 |
C21—C25—H25 | 125.9 | C82—C83—C84 | 122.1 (6) |
C32—C31—C36 | 117.6 (3) | C82—C83—H83 | 119.0 |
C32—C31—C1 | 122.9 (3) | C84—C83—H83 | 119.0 |
C36—C31—C1 | 119.1 (3) | C85—C84—C83 | 115.1 (5) |
C31—C32—C33 | 121.1 (3) | C85—C84—C87 | 122.6 (3) |
C31—C32—H32 | 119.5 | C83—C84—C87 | 122.3 (3) |
C33—C32—H32 | 119.5 | C86—C85—C84 | 121.6 (5) |
C34—C33—C32 | 120.1 (3) | C86—C85—H85 | 119.2 |
C34—C33—H33 | 119.9 | C84—C85—H85 | 119.2 |
C32—C33—H33 | 119.9 | N81—C86—C85 | 121.4 (5) |
C33—C34—C35 | 119.8 (3) | N81—C86—H86 | 119.3 |
C33—C34—H34 | 120.1 | C85—C86—H86 | 119.3 |
C35—C34—H34 | 120.1 | C77—C87—C84 | 117.3 (3) |
C34—C35—C36 | 119.7 (3) | C77—C87—H87 | 121.3 |
C34—C35—H35 | 120.2 | C84—C87—H87 | 121.3 |
C36—C35—H35 | 120.2 | C72A—N71A—C76A | 118.1 (7) |
C35—C36—C31 | 121.6 (3) | N71A—C72A—C73A | 125.4 (8) |
C35—C36—H36 | 119.2 | N71A—C72A—H72A | 117.3 |
C31—C36—H36 | 119.2 | C73A—C72A—H72A | 117.3 |
C42—C41—C46 | 118.4 (3) | C72A—C73A—C74A | 117.3 (11) |
C42—C41—C1 | 121.4 (3) | C72A—C73A—H73A | 121.4 |
C46—C41—C1 | 120.2 (3) | C74A—C73A—H73A | 121.4 |
C41—C42—C43 | 120.9 (3) | C75A—C74A—C73A | 116.6 (14) |
C41—C42—H42 | 119.5 | C75A—C74A—C77A | 121.6 (7) |
C43—C42—H42 | 119.5 | C73A—C74A—C77A | 121.7 (7) |
C44—C43—C42 | 119.7 (3) | C76A—C75A—C74A | 123.9 (16) |
C44—C43—H43 | 120.1 | C76A—C75A—H75A | 118.0 |
C42—C43—H43 | 120.1 | C74A—C75A—H75A | 118.0 |
C45—C44—C43 | 120.1 (3) | N71A—C76A—C75A | 118.6 (13) |
C45—C44—H44 | 119.9 | N71A—C76A—H76A | 120.7 |
C43—C44—H44 | 119.9 | C75A—C76A—H76A | 120.7 |
C44—C45—C46 | 120.2 (3) | C87A—C77A—C74A | 121.1 (5) |
C44—C45—H45 | 119.9 | C87A—C77A—H77A | 119.5 |
C46—C45—H45 | 119.9 | C74A—C77A—H77A | 119.5 |
C45—C46—C41 | 120.6 (3) | C86A—N81A—C82A | 114.2 (12) |
C45—C46—H46 | 119.7 | N81A—C82A—C83A | 124.6 (12) |
C41—C46—H46 | 119.7 | N81A—C82A—H82A | 117.7 |
C52—C51—C56 | 118.4 (3) | C83A—C82A—H82A | 117.7 |
C52—C51—C2 | 123.2 (3) | C82A—C83A—C84A | 119.5 (12) |
C56—C51—C2 | 118.4 (3) | C82A—C83A—H83A | 120.3 |
C51—C52—C53 | 121.3 (3) | C84A—C83A—H83A | 120.3 |
C51—C52—H52 | 119.4 | C85A—C84A—C83A | 117.5 (11) |
C53—C52—H52 | 119.4 | C85A—C84A—C87A | 121.0 (5) |
C54—C53—C52 | 120.0 (3) | C83A—C84A—C87A | 121.1 (6) |
C54—C53—H53 | 120.0 | C86A—C85A—C84A | 118.3 (10) |
C52—C53—H53 | 120.0 | C86A—C85A—H85A | 120.8 |
C53—C54—C55 | 119.3 (3) | C84A—C85A—H85A | 120.8 |
C53—C54—H54 | 120.4 | N81A—C86A—C85A | 125.7 (11) |
C55—C54—H54 | 120.4 | N81A—C86A—H86A | 117.1 |
C56—C55—C54 | 120.7 (3) | C85A—C86A—H86A | 117.1 |
C56—C55—H55 | 119.6 | C77A—C87A—C84A | 120.9 (5) |
C54—C55—H55 | 119.6 | C77A—C87A—H87A | 119.5 |
C55—C56—C51 | 120.3 (3) | C84A—C87A—H87A | 119.5 |
| | | |
O1—C1—C11—C15 | −147.2 (3) | C51—C52—C53—C54 | −0.6 (5) |
C31—C1—C11—C15 | 100.1 (3) | C52—C53—C54—C55 | 0.6 (5) |
C41—C1—C11—C15 | −25.3 (4) | C53—C54—C55—C56 | 0.2 (5) |
O1—C1—C11—C12 | 39.6 (4) | C54—C55—C56—C51 | −0.9 (5) |
C31—C1—C11—C12 | −73.1 (3) | C52—C51—C56—C55 | 0.9 (4) |
C41—C1—C11—C12 | 161.5 (3) | C2—C51—C56—C55 | −178.0 (3) |
C15—C11—C12—C13 | 0.7 (3) | O2—C2—C61—C62 | 10.1 (3) |
C1—C11—C12—C13 | 175.1 (3) | C21—C2—C61—C62 | −108.5 (3) |
C11—C12—C13—C14 | −0.5 (3) | C51—C2—C61—C62 | 128.3 (3) |
C12—C13—C14—C15 | 0.1 (3) | O2—C2—C61—C66 | −170.6 (2) |
C13—C14—C15—C11 | 0.3 (3) | C21—C2—C61—C66 | 70.9 (3) |
C12—C11—C15—C14 | −0.6 (3) | C51—C2—C61—C66 | −52.3 (3) |
C1—C11—C15—C14 | −174.7 (3) | C66—C61—C62—C63 | −4.0 (4) |
O2—C2—C21—C22 | −156.5 (3) | C2—C61—C62—C63 | 175.4 (2) |
C61—C2—C21—C22 | −38.6 (4) | C61—C62—C63—C64 | 0.3 (4) |
C51—C2—C21—C22 | 84.2 (4) | C62—C63—C64—C65 | 2.9 (4) |
O2—C2—C21—C25 | 30.0 (4) | C63—C64—C65—C66 | −2.4 (4) |
C61—C2—C21—C25 | 147.9 (3) | C64—C65—C66—C61 | −1.4 (4) |
C51—C2—C21—C25 | −89.3 (3) | C62—C61—C66—C65 | 4.5 (4) |
C25—C21—C22—C23 | 0.0 (3) | C2—C61—C66—C65 | −174.9 (2) |
C2—C21—C22—C23 | −174.4 (3) | C76—N71—C72—C73 | −3.1 (8) |
C21—C22—C23—C24 | −0.1 (3) | N71—C72—C73—C74 | 1.2 (8) |
C22—C23—C24—C25 | 0.2 (3) | C72—C73—C74—C75 | 2.0 (11) |
C23—C24—C25—C21 | −0.1 (3) | C72—C73—C74—C77 | −179.4 (5) |
C22—C21—C25—C24 | 0.1 (3) | C73—C74—C75—C76 | −3.0 (12) |
C2—C21—C25—C24 | 174.8 (3) | C77—C74—C75—C76 | 178.3 (8) |
O1—C1—C31—C32 | −106.4 (3) | C72—N71—C76—C75 | 2.0 (12) |
C11—C1—C31—C32 | 10.6 (4) | C74—C75—C76—N71 | 1.1 (14) |
C41—C1—C31—C32 | 136.2 (3) | C73—C74—C77—C87 | −161.5 (6) |
O1—C1—C31—C36 | 67.0 (3) | C75—C74—C77—C87 | 17.1 (10) |
C11—C1—C31—C36 | −176.0 (2) | C86—N81—C82—C83 | −4.6 (9) |
C41—C1—C31—C36 | −50.4 (3) | N81—C82—C83—C84 | 7.8 (9) |
C36—C31—C32—C33 | −3.8 (4) | C82—C83—C84—C85 | −5.9 (9) |
C1—C31—C32—C33 | 169.7 (3) | C82—C83—C84—C87 | 174.7 (6) |
C31—C32—C33—C34 | 1.2 (5) | C83—C84—C85—C86 | 1.4 (10) |
C32—C33—C34—C35 | 2.2 (5) | C87—C84—C85—C86 | −179.2 (6) |
C33—C34—C35—C36 | −2.7 (5) | C82—N81—C86—C85 | 0.2 (10) |
C34—C35—C36—C31 | 0.0 (5) | C84—C85—C86—N81 | 1.4 (11) |
C32—C31—C36—C35 | 3.2 (4) | C74—C77—C87—C84 | 172.0 (5) |
C1—C31—C36—C35 | −170.6 (3) | C83—C84—C87—C77 | −139.5 (6) |
O1—C1—C41—C42 | 14.2 (4) | C85—C84—C87—C77 | 41.2 (8) |
C11—C1—C41—C42 | −107.4 (3) | C76A—N71A—C72A—C73A | 0.0 (13) |
C31—C1—C41—C42 | 126.9 (3) | N71A—C72A—C73A—C74A | 1.4 (13) |
O1—C1—C41—C46 | −165.7 (3) | C72A—C73A—C74A—C75A | −1.1 (19) |
C11—C1—C41—C46 | 72.7 (4) | C72A—C73A—C74A—C77A | 175.6 (9) |
C31—C1—C41—C46 | −52.9 (4) | C73A—C74A—C75A—C76A | −1 (3) |
C46—C41—C42—C43 | −0.8 (5) | C77A—C74A—C75A—C76A | −177.3 (14) |
C1—C41—C42—C43 | 179.3 (3) | C72A—N71A—C76A—C75A | −2 (2) |
C41—C42—C43—C44 | 0.4 (5) | C74A—C75A—C76A—N71A | 2 (3) |
C42—C43—C44—C45 | −0.1 (5) | C73A—C74A—C77A—C87A | 31.1 (18) |
C43—C44—C45—C46 | 0.1 (5) | C75A—C74A—C77A—C87A | −152.3 (13) |
C44—C45—C46—C41 | −0.5 (5) | C86A—N81A—C82A—C83A | −0.8 (13) |
C42—C41—C46—C45 | 0.8 (5) | N81A—C82A—C83A—C84A | −0.8 (13) |
C1—C41—C46—C45 | −179.3 (3) | C82A—C83A—C84A—C85A | −0.6 (18) |
O2—C2—C51—C52 | −122.8 (3) | C82A—C83A—C84A—C87A | 172.4 (9) |
C61—C2—C51—C52 | 119.6 (3) | C83A—C84A—C85A—C86A | 3 (2) |
C21—C2—C51—C52 | −3.5 (4) | C87A—C84A—C85A—C86A | −169.6 (11) |
O2—C2—C51—C56 | 56.1 (3) | C82A—N81A—C86A—C85A | 4 (2) |
C61—C2—C51—C56 | −61.5 (3) | C84A—C85A—C86A—N81A | −6 (2) |
C21—C2—C51—C56 | 175.4 (2) | C74A—C77A—C87A—C84A | −174.5 (10) |
C56—C51—C52—C53 | −0.2 (5) | C83A—C84A—C87A—C77A | 10.8 (16) |
C2—C51—C52—C53 | 178.7 (3) | C85A—C84A—C87A—C77A | −176.5 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.05 | 2.787 (3) | 147 |
O2—H2···N71 | 0.84 | 1.96 | 2.786 (4) | 168 |
(II) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,6-diaminohexane
top
Crystal data top
[Fe(C18H15O)2]2·C6H16N2 | Z = 1 |
Mr = 1217.11 | F(000) = 642 |
Triclinic, P1 | Dx = 1.307 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2027 (2) Å | Cell parameters from 6769 reflections |
b = 11.7067 (2) Å | θ = 3.0–27.6° |
c = 14.6172 (3) Å | µ = 0.52 mm−1 |
α = 84.9780 (9)° | T = 150 K |
β = 70.2454 (8)° | Block, orange |
γ = 70.3612 (8)° | 0.40 × 0.30 × 0.28 mm |
V = 1546.88 (5) Å3 | |
Data collection top
KappaCCD diffractometer | 7106 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6398 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ϕ scans, and ω scans with κ offsets | θmax = 27.6°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = 0→13 |
Tmin = 0.818, Tmax = 0.867 | k = −13→15 |
23031 measured reflections | l = −17→19 |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0288P)2 + 0.7055P] where P = (Fo2 + 2Fc2)/3 |
7106 reflections | (Δ/σ)max = 0.002 |
391 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Crystal data top
[Fe(C18H15O)2]2·C6H16N2 | γ = 70.3612 (8)° |
Mr = 1217.11 | V = 1546.88 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.2027 (2) Å | Mo Kα radiation |
b = 11.7067 (2) Å | µ = 0.52 mm−1 |
c = 14.6172 (3) Å | T = 150 K |
α = 84.9780 (9)° | 0.40 × 0.30 × 0.28 mm |
β = 70.2454 (8)° | |
Data collection top
KappaCCD diffractometer | 7106 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 6398 reflections with I > 2σ(I) |
Tmin = 0.818, Tmax = 0.867 | Rint = 0.032 |
23031 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.30 e Å−3 |
7106 reflections | Δρmin = −0.49 e Å−3 |
391 parameters | |
Special details top
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. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 1.102756 (19) | 0.603013 (16) | 0.118594 (13) | 0.01850 (6) | |
O1 | 1.22021 (12) | 0.38833 (9) | 0.28265 (7) | 0.0288 (2) | |
O2 | 1.07938 (10) | 0.61792 (8) | 0.37540 (7) | 0.02193 (19) | |
C11 | 1.23957 (14) | 0.42780 (11) | 0.11478 (9) | 0.0199 (2) | |
C12 | 1.32152 (14) | 0.50991 (12) | 0.09818 (10) | 0.0238 (3) | |
C13 | 1.30528 (15) | 0.57778 (13) | 0.01473 (11) | 0.0272 (3) | |
C14 | 1.21479 (16) | 0.53766 (12) | −0.02141 (10) | 0.0256 (3) | |
C15 | 1.17368 (15) | 0.44508 (12) | 0.04011 (9) | 0.0217 (3) | |
C16 | 1.23792 (14) | 0.33436 (12) | 0.19344 (10) | 0.0214 (3) | |
C21 | 1.00859 (14) | 0.71657 (11) | 0.24063 (9) | 0.0198 (2) | |
C22 | 1.01670 (16) | 0.78399 (12) | 0.15362 (10) | 0.0246 (3) | |
C23 | 0.93524 (16) | 0.74973 (13) | 0.10425 (11) | 0.0286 (3) | |
C24 | 0.87772 (15) | 0.66159 (14) | 0.15982 (11) | 0.0281 (3) | |
C25 | 0.92310 (14) | 0.64044 (12) | 0.24339 (10) | 0.0231 (3) | |
C26 | 1.06110 (14) | 0.72875 (11) | 0.32413 (9) | 0.0193 (2) | |
C31 | 1.38735 (15) | 0.23218 (12) | 0.16780 (11) | 0.0232 (3) | |
C32 | 1.47966 (16) | 0.20220 (13) | 0.07243 (12) | 0.0311 (3) | |
C33 | 1.61345 (18) | 0.10722 (15) | 0.05239 (14) | 0.0412 (4) | |
C34 | 1.65518 (18) | 0.04294 (15) | 0.12717 (16) | 0.0433 (4) | |
C35 | 1.56311 (19) | 0.07138 (14) | 0.22220 (15) | 0.0404 (4) | |
C36 | 1.42965 (17) | 0.16554 (13) | 0.24287 (12) | 0.0313 (3) | |
C41 | 1.11510 (15) | 0.27965 (12) | 0.20722 (10) | 0.0241 (3) | |
C42 | 1.12952 (17) | 0.19521 (13) | 0.13971 (11) | 0.0291 (3) | |
C43 | 1.0161 (2) | 0.14910 (15) | 0.15039 (13) | 0.0387 (4) | |
C44 | 0.8879 (2) | 0.18578 (18) | 0.22908 (16) | 0.0489 (5) | |
C45 | 0.8743 (2) | 0.26717 (19) | 0.29748 (17) | 0.0539 (5) | |
C46 | 0.98691 (18) | 0.31386 (15) | 0.28673 (13) | 0.0379 (4) | |
C51 | 0.94642 (14) | 0.83301 (11) | 0.39521 (10) | 0.0210 (3) | |
C52 | 0.82726 (17) | 0.91660 (13) | 0.37523 (11) | 0.0303 (3) | |
C53 | 0.72539 (18) | 1.00727 (15) | 0.44409 (12) | 0.0376 (4) | |
C54 | 0.74232 (18) | 1.01431 (14) | 0.53279 (12) | 0.0364 (4) | |
C55 | 0.86129 (19) | 0.93061 (15) | 0.55342 (11) | 0.0348 (3) | |
C56 | 0.96293 (17) | 0.84131 (13) | 0.48512 (11) | 0.0286 (3) | |
C61 | 1.20986 (14) | 0.75042 (12) | 0.28661 (9) | 0.0210 (3) | |
C62 | 1.21892 (15) | 0.86237 (12) | 0.24903 (10) | 0.0246 (3) | |
C63 | 1.35396 (17) | 0.88200 (14) | 0.21146 (11) | 0.0304 (3) | |
C64 | 1.48202 (17) | 0.79038 (15) | 0.21195 (12) | 0.0348 (3) | |
C65 | 1.47408 (16) | 0.67947 (15) | 0.25065 (12) | 0.0339 (3) | |
C66 | 1.33900 (15) | 0.65931 (13) | 0.28788 (11) | 0.0270 (3) | |
N1 | 0.81471 (13) | 0.60480 (11) | 0.50091 (9) | 0.0276 (3) | |
C2 | 0.67658 (16) | 0.68502 (13) | 0.48746 (11) | 0.0287 (3) | |
C3 | 0.54495 (16) | 0.63958 (14) | 0.53022 (12) | 0.0317 (3) | |
C4 | 0.56871 (16) | 0.51897 (14) | 0.48401 (12) | 0.0320 (3) | |
H1 | 1.1696 | 0.4620 | 0.2854 | 0.043* | |
H2 | 0.9972 | 0.6174 | 0.4142 | 0.033* | |
H12 | 1.3773 | 0.5178 | 0.1363 | 0.029* | |
H13 | 1.3476 | 0.6392 | −0.0121 | 0.033* | |
H14 | 1.1865 | 0.5673 | −0.0769 | 0.031* | |
H15 | 1.1132 | 0.4024 | 0.0328 | 0.026* | |
H22 | 1.0672 | 0.8414 | 0.1323 | 0.029* | |
H23 | 0.9221 | 0.7808 | 0.0445 | 0.034* | |
H24 | 0.8191 | 0.6234 | 0.1440 | 0.034* | |
H25 | 0.9005 | 0.5850 | 0.2928 | 0.028* | |
H32 | 1.4517 | 0.2465 | 0.0206 | 0.037* | |
H33 | 1.6758 | 0.0869 | −0.0130 | 0.049* | |
H34 | 1.7469 | −0.0207 | 0.1135 | 0.052* | |
H35 | 1.5912 | 0.0263 | 0.2737 | 0.048* | |
H36 | 1.3671 | 0.1845 | 0.3084 | 0.038* | |
H42 | 1.2178 | 0.1689 | 0.0858 | 0.035* | |
H43 | 1.0268 | 0.0923 | 0.1035 | 0.046* | |
H44 | 0.8097 | 0.1553 | 0.2361 | 0.059* | |
H45 | 0.7871 | 0.2914 | 0.3523 | 0.065* | |
H46 | 0.9760 | 0.3698 | 0.3343 | 0.045* | |
H52 | 0.8144 | 0.9124 | 0.3143 | 0.036* | |
H53 | 0.6440 | 1.0644 | 0.4296 | 0.045* | |
H54 | 0.6731 | 1.0760 | 0.5794 | 0.044* | |
H55 | 0.8732 | 0.9345 | 0.6147 | 0.042* | |
H56 | 1.0448 | 0.7851 | 0.4996 | 0.034* | |
H62 | 1.1316 | 0.9260 | 0.2491 | 0.029* | |
H63 | 1.3585 | 0.9584 | 0.1854 | 0.036* | |
H64 | 1.5745 | 0.8034 | 0.1860 | 0.042* | |
H65 | 1.5615 | 0.6167 | 0.2518 | 0.041* | |
H66 | 1.3349 | 0.5830 | 0.3143 | 0.032* | |
H1A | 0.8128 | 0.6161 | 0.5622 | 0.041* | |
H1B | 0.8242 | 0.5261 | 0.4919 | 0.041* | |
H2A | 0.6938 | 0.6962 | 0.4169 | 0.034* | |
H2B | 0.6512 | 0.7655 | 0.5176 | 0.034* | |
H3A | 0.4567 | 0.7013 | 0.5209 | 0.038* | |
H3B | 0.5258 | 0.6298 | 0.6010 | 0.038* | |
H4A | 0.6016 | 0.5255 | 0.4124 | 0.038* | |
H4B | 0.6484 | 0.4549 | 0.5011 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01683 (10) | 0.01760 (10) | 0.01911 (10) | −0.00334 (7) | −0.00503 (7) | −0.00244 (7) |
O1 | 0.0383 (6) | 0.0212 (5) | 0.0238 (5) | −0.0009 (4) | −0.0143 (4) | −0.0038 (4) |
O2 | 0.0215 (4) | 0.0191 (4) | 0.0229 (5) | −0.0048 (4) | −0.0064 (4) | 0.0015 (4) |
C11 | 0.0167 (6) | 0.0180 (6) | 0.0204 (6) | −0.0017 (5) | −0.0034 (5) | −0.0037 (5) |
C12 | 0.0161 (6) | 0.0224 (6) | 0.0291 (7) | −0.0040 (5) | −0.0040 (5) | −0.0043 (5) |
C13 | 0.0223 (6) | 0.0235 (7) | 0.0278 (7) | −0.0070 (5) | 0.0016 (5) | −0.0012 (5) |
C14 | 0.0290 (7) | 0.0235 (6) | 0.0182 (6) | −0.0047 (5) | −0.0034 (5) | −0.0020 (5) |
C15 | 0.0233 (6) | 0.0198 (6) | 0.0197 (6) | −0.0043 (5) | −0.0058 (5) | −0.0042 (5) |
C16 | 0.0215 (6) | 0.0192 (6) | 0.0217 (6) | −0.0033 (5) | −0.0074 (5) | −0.0022 (5) |
C21 | 0.0169 (6) | 0.0183 (6) | 0.0212 (6) | −0.0014 (5) | −0.0056 (5) | −0.0045 (5) |
C22 | 0.0285 (7) | 0.0173 (6) | 0.0256 (7) | −0.0016 (5) | −0.0113 (6) | −0.0024 (5) |
C23 | 0.0290 (7) | 0.0253 (7) | 0.0273 (7) | 0.0043 (6) | −0.0152 (6) | −0.0062 (5) |
C24 | 0.0172 (6) | 0.0338 (7) | 0.0307 (7) | −0.0012 (5) | −0.0083 (6) | −0.0131 (6) |
C25 | 0.0166 (6) | 0.0259 (6) | 0.0234 (7) | −0.0048 (5) | −0.0029 (5) | −0.0060 (5) |
C26 | 0.0197 (6) | 0.0173 (6) | 0.0200 (6) | −0.0044 (5) | −0.0068 (5) | −0.0006 (5) |
C31 | 0.0204 (6) | 0.0176 (6) | 0.0334 (7) | −0.0051 (5) | −0.0113 (6) | −0.0024 (5) |
C32 | 0.0261 (7) | 0.0245 (7) | 0.0366 (8) | −0.0032 (6) | −0.0071 (6) | −0.0026 (6) |
C33 | 0.0271 (8) | 0.0307 (8) | 0.0524 (11) | −0.0008 (6) | −0.0027 (7) | −0.0079 (7) |
C34 | 0.0260 (8) | 0.0256 (8) | 0.0745 (13) | 0.0020 (6) | −0.0202 (8) | −0.0063 (8) |
C35 | 0.0381 (9) | 0.0271 (8) | 0.0630 (12) | −0.0023 (7) | −0.0336 (9) | 0.0014 (7) |
C36 | 0.0333 (8) | 0.0253 (7) | 0.0388 (8) | −0.0052 (6) | −0.0199 (7) | −0.0008 (6) |
C41 | 0.0226 (6) | 0.0212 (6) | 0.0269 (7) | −0.0063 (5) | −0.0082 (5) | 0.0059 (5) |
C42 | 0.0311 (7) | 0.0295 (7) | 0.0295 (7) | −0.0134 (6) | −0.0112 (6) | 0.0051 (6) |
C43 | 0.0460 (10) | 0.0366 (8) | 0.0461 (10) | −0.0237 (7) | −0.0233 (8) | 0.0118 (7) |
C44 | 0.0371 (9) | 0.0474 (10) | 0.0700 (13) | −0.0274 (8) | −0.0172 (9) | 0.0157 (9) |
C45 | 0.0319 (9) | 0.0516 (11) | 0.0645 (13) | −0.0195 (8) | 0.0068 (9) | 0.0016 (9) |
C46 | 0.0315 (8) | 0.0334 (8) | 0.0395 (9) | −0.0115 (7) | 0.0012 (7) | −0.0008 (7) |
C51 | 0.0203 (6) | 0.0191 (6) | 0.0217 (6) | −0.0066 (5) | −0.0034 (5) | −0.0028 (5) |
C52 | 0.0304 (7) | 0.0270 (7) | 0.0274 (7) | −0.0004 (6) | −0.0097 (6) | −0.0044 (6) |
C53 | 0.0343 (8) | 0.0294 (8) | 0.0364 (9) | 0.0045 (6) | −0.0086 (7) | −0.0073 (6) |
C54 | 0.0376 (8) | 0.0280 (7) | 0.0313 (8) | −0.0041 (6) | 0.0001 (7) | −0.0109 (6) |
C55 | 0.0420 (9) | 0.0355 (8) | 0.0242 (7) | −0.0103 (7) | −0.0077 (7) | −0.0085 (6) |
C56 | 0.0301 (7) | 0.0286 (7) | 0.0264 (7) | −0.0066 (6) | −0.0104 (6) | −0.0040 (6) |
C61 | 0.0207 (6) | 0.0228 (6) | 0.0195 (6) | −0.0064 (5) | −0.0063 (5) | −0.0037 (5) |
C62 | 0.0240 (7) | 0.0226 (6) | 0.0271 (7) | −0.0067 (5) | −0.0085 (6) | −0.0022 (5) |
C63 | 0.0303 (7) | 0.0290 (7) | 0.0334 (8) | −0.0142 (6) | −0.0078 (6) | 0.0004 (6) |
C64 | 0.0236 (7) | 0.0399 (9) | 0.0410 (9) | −0.0139 (6) | −0.0062 (6) | −0.0024 (7) |
C65 | 0.0209 (7) | 0.0360 (8) | 0.0418 (9) | −0.0054 (6) | −0.0101 (6) | −0.0002 (7) |
C66 | 0.0235 (7) | 0.0258 (7) | 0.0309 (7) | −0.0058 (5) | −0.0102 (6) | 0.0001 (6) |
N1 | 0.0270 (6) | 0.0301 (6) | 0.0263 (6) | −0.0112 (5) | −0.0084 (5) | 0.0027 (5) |
C2 | 0.0256 (7) | 0.0280 (7) | 0.0292 (7) | −0.0079 (6) | −0.0057 (6) | 0.0004 (6) |
C3 | 0.0247 (7) | 0.0320 (8) | 0.0340 (8) | −0.0086 (6) | −0.0039 (6) | −0.0028 (6) |
C4 | 0.0257 (7) | 0.0330 (8) | 0.0361 (8) | −0.0101 (6) | −0.0071 (6) | −0.0026 (6) |
Geometric parameters (Å, º) top
Fe1—C23 | 2.0301 (13) | C35—H35 | 0.95 |
Fe1—C22 | 2.0390 (13) | C36—H36 | 0.95 |
Fe1—C15 | 2.0419 (12) | C41—C46 | 1.387 (2) |
Fe1—C24 | 2.0454 (14) | C41—C42 | 1.395 (2) |
Fe1—C14 | 2.0458 (13) | C42—C43 | 1.392 (2) |
Fe1—C11 | 2.0498 (12) | C42—H42 | 0.95 |
Fe1—C13 | 2.0517 (14) | C43—C44 | 1.382 (3) |
Fe1—C25 | 2.0540 (13) | C43—H43 | 0.95 |
Fe1—C12 | 2.0567 (13) | C44—C45 | 1.383 (3) |
Fe1—C21 | 2.0665 (12) | C44—H44 | 0.95 |
O1—C16 | 1.4284 (15) | C45—C46 | 1.389 (3) |
O1—H1 | 0.84 | C45—H45 | 0.95 |
O2—C26 | 1.4288 (15) | C46—H46 | 0.95 |
O2—H2 | 0.84 | C51—C52 | 1.3824 (19) |
C11—C12 | 1.4298 (19) | C51—C56 | 1.3957 (19) |
C11—C15 | 1.4319 (18) | C52—C53 | 1.399 (2) |
C11—C16 | 1.5159 (18) | C52—H52 | 0.95 |
C12—C13 | 1.423 (2) | C53—C54 | 1.377 (2) |
C12—H12 | 0.95 | C53—H53 | 0.95 |
C13—C14 | 1.420 (2) | C54—C55 | 1.386 (2) |
C13—H13 | 0.95 | C54—H54 | 0.95 |
C14—C15 | 1.428 (2) | C55—C56 | 1.385 (2) |
C14—H14 | 0.95 | C55—H55 | 0.95 |
C15—H15 | 0.95 | C56—H56 | 0.95 |
C16—C31 | 1.5369 (17) | C61—C66 | 1.3937 (18) |
C16—C41 | 1.5386 (19) | C61—C62 | 1.3961 (19) |
C21—C22 | 1.4298 (19) | C62—C63 | 1.390 (2) |
C21—C25 | 1.4315 (18) | C62—H62 | 0.95 |
C21—C26 | 1.5235 (17) | C63—C64 | 1.386 (2) |
C22—C23 | 1.4327 (19) | C63—H63 | 0.95 |
C22—H22 | 0.95 | C64—C65 | 1.387 (2) |
C23—C24 | 1.417 (2) | C64—H64 | 0.95 |
C23—H23 | 0.95 | C65—C66 | 1.393 (2) |
C24—C25 | 1.421 (2) | C65—H65 | 0.95 |
C24—H24 | 0.95 | C66—H66 | 0.95 |
C25—H25 | 0.95 | N1—C2 | 1.4738 (18) |
C26—C61 | 1.5299 (18) | N1—H1A | 0.91 |
C26—C51 | 1.5422 (17) | N1—H1B | 0.91 |
C31—C32 | 1.389 (2) | C2—C3 | 1.527 (2) |
C31—C36 | 1.394 (2) | C2—H2A | 0.99 |
C32—C33 | 1.397 (2) | C2—H2B | 0.99 |
C32—H32 | 0.95 | C3—C4 | 1.528 (2) |
C33—C34 | 1.378 (3) | C3—H3A | 0.99 |
C33—H33 | 0.95 | C3—H3B | 0.99 |
C34—C35 | 1.383 (3) | C4—C4i | 1.523 (3) |
C34—H34 | 0.95 | C4—H4A | 0.99 |
C35—C36 | 1.390 (2) | C4—H4B | 0.99 |
| | | |
C16—O1—H1 | 109.5 | C44—C43—H43 | 120.0 |
C26—O2—H2 | 109.5 | C42—C43—H43 | 120.0 |
C12—C11—C15 | 107.41 (12) | C43—C44—C45 | 119.44 (16) |
C12—C11—C16 | 123.97 (12) | C43—C44—H44 | 120.3 |
C15—C11—C16 | 128.43 (12) | C45—C44—H44 | 120.3 |
C13—C12—C11 | 108.35 (12) | C44—C45—C46 | 120.60 (18) |
C13—C12—H12 | 125.8 | C44—C45—H45 | 119.7 |
C11—C12—H12 | 125.8 | C46—C45—H45 | 119.7 |
C14—C13—C12 | 108.09 (12) | C41—C46—C45 | 120.63 (17) |
C14—C13—H13 | 126.0 | C41—C46—H46 | 119.7 |
C12—C13—H13 | 126.0 | C45—C46—H46 | 119.7 |
C13—C14—C15 | 108.14 (12) | C52—C51—C56 | 118.63 (12) |
C13—C14—H14 | 125.9 | C52—C51—C26 | 123.48 (12) |
C15—C14—H14 | 125.9 | C56—C51—C26 | 117.87 (12) |
C14—C15—C11 | 108.02 (12) | C51—C52—C53 | 120.47 (14) |
C14—C15—H15 | 126.0 | C51—C52—H52 | 119.8 |
C11—C15—H15 | 126.0 | C53—C52—H52 | 119.8 |
O1—C16—C11 | 109.85 (10) | C54—C53—C52 | 120.44 (15) |
O1—C16—C31 | 105.48 (10) | C54—C53—H53 | 119.8 |
C11—C16—C31 | 110.30 (11) | C52—C53—H53 | 119.8 |
O1—C16—C41 | 110.49 (11) | C53—C54—C55 | 119.40 (14) |
C11—C16—C41 | 111.26 (11) | C53—C54—H54 | 120.3 |
C31—C16—C41 | 109.31 (10) | C55—C54—H54 | 120.3 |
C22—C21—C25 | 107.19 (11) | C56—C55—C54 | 120.29 (14) |
C22—C21—C26 | 129.21 (12) | C56—C55—H55 | 119.9 |
C25—C21—C26 | 123.22 (12) | C54—C55—H55 | 119.9 |
C21—C22—C23 | 107.99 (13) | C55—C56—C51 | 120.77 (14) |
C21—C22—H22 | 126.0 | C55—C56—H56 | 119.6 |
C23—C22—H22 | 126.0 | C51—C56—H56 | 119.6 |
C24—C23—C22 | 108.21 (12) | C66—C61—C62 | 118.54 (13) |
C24—C23—H23 | 125.9 | C66—C61—C26 | 121.19 (12) |
C22—C23—H23 | 125.9 | C62—C61—C26 | 120.26 (11) |
C23—C24—C25 | 107.97 (12) | C63—C62—C61 | 120.92 (13) |
C23—C24—H24 | 126.0 | C63—C62—H62 | 119.5 |
C25—C24—H24 | 126.0 | C61—C62—H62 | 119.5 |
C24—C25—C21 | 108.63 (13) | C64—C63—C62 | 120.12 (14) |
C24—C25—H25 | 125.7 | C64—C63—H63 | 119.9 |
C21—C25—H25 | 125.7 | C62—C63—H63 | 119.9 |
O2—C26—C21 | 108.43 (10) | C63—C64—C65 | 119.47 (14) |
O2—C26—C61 | 107.96 (10) | C63—C64—H64 | 120.3 |
C21—C26—C61 | 111.27 (11) | C65—C64—H64 | 120.3 |
O2—C26—C51 | 108.67 (10) | C64—C65—C66 | 120.55 (14) |
C21—C26—C51 | 110.63 (10) | C64—C65—H65 | 119.7 |
C61—C26—C51 | 109.79 (10) | C66—C65—H65 | 119.7 |
C32—C31—C36 | 119.04 (13) | C65—C66—C61 | 120.38 (14) |
C32—C31—C16 | 122.26 (12) | C65—C66—H66 | 119.8 |
C36—C31—C16 | 118.68 (13) | C61—C66—H66 | 119.8 |
C31—C32—C33 | 120.31 (15) | C2—N1—H1A | 109.5 |
C31—C32—H32 | 119.8 | C2—N1—H1B | 109.5 |
C33—C32—H32 | 119.8 | H1A—N1—H1B | 109.5 |
C34—C33—C32 | 120.21 (17) | N1—C2—C3 | 114.98 (12) |
C34—C33—H33 | 119.9 | N1—C2—H2A | 108.5 |
C32—C33—H33 | 119.9 | C3—C2—H2A | 108.5 |
C33—C34—C35 | 119.80 (14) | N1—C2—H2B | 108.5 |
C33—C34—H34 | 120.1 | C3—C2—H2B | 108.5 |
C35—C34—H34 | 120.1 | H2A—C2—H2B | 107.5 |
C34—C35—C36 | 120.42 (16) | C2—C3—C4 | 112.94 (12) |
C34—C35—H35 | 119.8 | C2—C3—H3A | 109.0 |
C36—C35—H35 | 119.8 | C4—C3—H3A | 109.0 |
C35—C36—C31 | 120.21 (16) | C2—C3—H3B | 109.0 |
C35—C36—H36 | 119.9 | C4—C3—H3B | 109.0 |
C31—C36—H36 | 119.9 | H3A—C3—H3B | 107.8 |
C46—C41—C42 | 118.45 (14) | C4i—C4—C3 | 113.48 (16) |
C46—C41—C16 | 120.72 (13) | C4i—C4—H4A | 108.9 |
C42—C41—C16 | 120.84 (13) | C3—C4—H4A | 108.9 |
C43—C42—C41 | 120.77 (15) | C4i—C4—H4B | 108.9 |
C43—C42—H42 | 119.6 | C3—C4—H4B | 108.9 |
C41—C42—H42 | 119.6 | H4A—C4—H4B | 107.7 |
C44—C43—C42 | 120.08 (17) | | |
| | | |
C15—C11—C12—C13 | 0.49 (14) | C31—C16—C41—C46 | 133.38 (14) |
C16—C11—C12—C13 | 175.90 (11) | O1—C16—C41—C42 | −162.76 (12) |
C11—C12—C13—C14 | −0.55 (15) | C11—C16—C41—C42 | 74.95 (15) |
C12—C13—C14—C15 | 0.40 (15) | C31—C16—C41—C42 | −47.10 (17) |
C13—C14—C15—C11 | −0.09 (15) | C46—C41—C42—C43 | 1.9 (2) |
C12—C11—C15—C14 | −0.25 (14) | C16—C41—C42—C43 | −177.65 (13) |
C16—C11—C15—C14 | −175.38 (12) | C41—C42—C43—C44 | −0.7 (2) |
C12—C11—C16—O1 | 45.02 (16) | C42—C43—C44—C45 | −0.9 (3) |
C15—C11—C16—O1 | −140.59 (13) | C43—C44—C45—C46 | 1.2 (3) |
C12—C11—C16—C31 | −70.83 (15) | C42—C41—C46—C45 | −1.5 (2) |
C15—C11—C16—C31 | 103.56 (15) | C16—C41—C46—C45 | 178.03 (16) |
C12—C11—C16—C41 | 167.69 (12) | C44—C45—C46—C41 | 0.0 (3) |
C15—C11—C16—C41 | −17.92 (18) | O2—C26—C51—C52 | −130.03 (14) |
C25—C21—C22—C23 | 0.54 (14) | C21—C26—C51—C52 | −11.09 (18) |
C26—C21—C22—C23 | −172.45 (12) | C61—C26—C51—C52 | 112.09 (15) |
C21—C22—C23—C24 | −0.25 (15) | O2—C26—C51—C56 | 48.62 (16) |
C22—C23—C24—C25 | −0.15 (15) | C21—C26—C51—C56 | 167.55 (12) |
C23—C24—C25—C21 | 0.49 (15) | C61—C26—C51—C56 | −69.26 (15) |
C22—C21—C25—C24 | −0.64 (14) | C56—C51—C52—C53 | −0.2 (2) |
C26—C21—C25—C24 | 172.87 (11) | C26—C51—C52—C53 | 178.47 (14) |
C22—C21—C26—O2 | −159.11 (12) | C51—C52—C53—C54 | −0.1 (3) |
C25—C21—C26—O2 | 28.89 (16) | C52—C53—C54—C55 | 0.0 (3) |
C22—C21—C26—C61 | −40.52 (17) | C53—C54—C55—C56 | 0.5 (3) |
C25—C21—C26—C61 | 147.48 (12) | C54—C55—C56—C51 | −0.9 (2) |
C22—C21—C26—C51 | 81.81 (16) | C52—C51—C56—C55 | 0.7 (2) |
C25—C21—C26—C51 | −90.19 (14) | C26—C51—C56—C55 | −178.05 (14) |
O1—C16—C31—C32 | −144.88 (13) | O2—C26—C61—C66 | 12.33 (16) |
C11—C16—C31—C32 | −26.32 (17) | C21—C26—C61—C66 | −106.54 (14) |
C41—C16—C31—C32 | 96.30 (15) | C51—C26—C61—C66 | 130.65 (13) |
O1—C16—C31—C36 | 36.75 (16) | O2—C26—C61—C62 | −168.48 (11) |
C11—C16—C31—C36 | 155.31 (12) | C21—C26—C61—C62 | 72.65 (15) |
C41—C16—C31—C36 | −82.07 (15) | C51—C26—C61—C62 | −50.17 (16) |
C36—C31—C32—C33 | −0.5 (2) | C66—C61—C62—C63 | 1.5 (2) |
C16—C31—C32—C33 | −178.90 (14) | C26—C61—C62—C63 | −177.67 (12) |
C31—C32—C33—C34 | −0.3 (3) | C61—C62—C63—C64 | −0.8 (2) |
C32—C33—C34—C35 | 1.1 (3) | C62—C63—C64—C65 | −0.4 (2) |
C33—C34—C35—C36 | −0.9 (3) | C63—C64—C65—C66 | 0.7 (2) |
C34—C35—C36—C31 | 0.1 (2) | C64—C65—C66—C61 | 0.1 (2) |
C32—C31—C36—C35 | 0.7 (2) | C62—C61—C66—C65 | −1.2 (2) |
C16—C31—C36—C35 | 179.09 (13) | C26—C61—C66—C65 | 178.01 (13) |
O1—C16—C41—C46 | 17.73 (18) | N1—C2—C3—C4 | −61.89 (18) |
C11—C16—C41—C46 | −104.57 (15) | C2—C3—C4—C4i | −172.22 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.09 | 2.8021 (13) | 142 |
O2—H2···N1 | 0.84 | 1.91 | 2.7499 (16) | 176 |
N1—H1A···O1ii | 0.91 | 2.18 | 3.0669 (16) | 166 |
Symmetry code: (ii) −x+2, −y+1, −z+1. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | [Fe(C18H15O)2]·C12H10N2 | [Fe(C18H15O)2]2·C6H16N2 |
Mr | 732.67 | 1217.11 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 |
a, b, c (Å) | 9.6393 (4), 11.4219 (5), 17.7338 (10) | 10.2027 (2), 11.7067 (2), 14.6172 (3) |
α, β, γ (°) | 76.7680 (18), 87.4580 (17), 74.064 (3) | 84.9780 (9), 70.2454 (8), 70.3612 (8) |
V (Å3) | 1827.24 (15) | 1546.88 (5) |
Z | 2 | 1 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.46 | 0.52 |
Crystal size (mm) | 0.23 × 0.16 × 0.14 | 0.40 × 0.30 × 0.28 |
|
Data collection |
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.902, 0.939 | 0.818, 0.867 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16969, 6460, 4709 | 23031, 7106, 6398 |
Rint | 0.060 | 0.032 |
(sin θ/λ)max (Å−1) | 0.596 | 0.651 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.125, 1.03 | 0.032, 0.082, 1.03 |
No. of reflections | 6460 | 7106 |
No. of parameters | 526 | 391 |
No. of restraints | 64 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.48 | 0.30, −0.49 |
Selected torsion angles (º) for (I) topC73—C74—C77—C87 | −161.5 (6) | C73A—C74A—C77A—C87A | 31.1 (18) |
C75—C74—C77—C87 | 17.1 (10) | C75A—C74A—C77A—C87A | −152.3 (13) |
C83—C84—C87—C77 | −139.5 (6) | C83A—C84A—C87A—C77A | 10.8 (16) |
C85—C84—C87—C77 | 41.2 (8) | C85A—C84A—C87A—C77A | −176.5 (11) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.05 | 2.787 (3) | 147 |
O2—H2···N71 | 0.84 | 1.96 | 2.786 (4) | 168 |
Selected torsion angles (º) for (II) topN1—C2—C3—C4 | −61.89 (18) | C2—C3—C4—C4i | −172.22 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 | 2.09 | 2.8021 (13) | 142 |
O2—H2···N1 | 0.84 | 1.91 | 2.7499 (16) | 176 |
N1—H1A···O1ii | 0.91 | 2.18 | 3.0669 (16) | 166 |
Symmetry code: (ii) −x+2, −y+1, −z+1. |
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The organometallic diol ferrocene-1,1'-diylbis(diphenylmethanol), [Fe(C5H4CPh2OH)2], forms a 1: 1 hydrogen-bonded adduct with 4,4'-bipyridyl in which only half of the bipyridyl molecules are involved in the supramolecular aggregation; this takes the form of a finite centrosymmetric three-component aggregate diol–diamine–diol, while the remainder of the bipyridyl molecules occupy isolated sites within the structure (Glidewell et al., 1994). By contrast, the 1:1 adduct formed by this diol with 1,2-bis(4-pyridyl)ethane crystallizes as a finite monomeric adduct in which one of the N atoms plays no part in the hydrogen bonding (Zakaria et al., 2001). The 1:1 adduct formed by the ferrocenediol with 1,2-diaminoethane, by contrast, exhibits a much more complex structure, in the form of two independent four-molecule aggregates, (diol)2.(diamine)2, both of which are centrosymmetric, but which exhibit different patterns of hydrogen bonds (Zakaria et al., 2001). Continuing this theme, we have now synthesized and structurally characterized two further adducts with related diamines, the 1:1 adduct with trans-1,2-bis(4-pyridyl)ethene, [Fe(C18H15O)2]·C12H10N2, (I), and the 2:1 adduct with 1,6-diaminohexane, 2[Fe(C18H15O)2]·C6H16N2, (II).
Compound (I) consists of finite 1:1 aggregates (Fig. 1); in addition to an intermolecular O—H···O hydrogen bond within the diol (Table 2), there is an O—H···N hydrogen bond linking the molecular components. By contrast with the fully ordered diamine in the analogous 1,2-bis(4-pyridyl)ethane adduct, in (I), the 1,2-bis(4-pyridyl)ethene molecules exhibit orientational disorder over two sets of sites, of a type previously observed in the 1:1 adduct of this diamine with 4,4'-sulfonyldiphenol (Ferguson et al., 1999). The two sets of sites, whose refined site-occupation factors are 0.601 (5) and 0.399 (5), can be most simply envisaged as resulting from a 180° rotation about a line which approximates to the N···N vector, so that the heteroaromatic ring position are similar in the two orientations, but the two central C═C bonds are nearly orthogonal. In neither orientation of the diamine does the remote N act as a hydrogen-bond acceptor.
In compound (II), the 1,6-diaminohexane component lies across a centre of inversion in space group P1, selected for the sake of convenience as that at (1/2, 1/2, 1/2), while the ferrocenediol lies in a general position. There is the usual intramolecular O—H···O hydrogen bond within the ferrocenediol, and the free hydroxyl group forms an O—H···N hydrogen bond with the amine (Table 4); a centrosymmetric three-molecule diol–diamine–diol aggregate thus results. In addition, the amino N1 atom at (x, y, z), which is a component of the three-molecule aggregate centred at (1/2, 1/2, 1/2), acts as a hydrogen-bond donor, via H1A, to O1 at (2 - x, 1 - y, 1 - z), which is a component of the aggregate centred at (1.5, 1/2, 1/2); N1 at (2 - x, 1 - y, 1 - z), in turn, acts as donor to O1 at (x, y, z), producing a centrosymmetric R66(12) ring centred at (1, 1/2, 1/2). The symmetry-related N1 atom in the aggregate centred at (1/2, 1/2, 1/2) is at (1 - x, 1 - y, 1 - z), and this acts as a hydrogen-bond donor to O1 at (-1 + x, y, z), part of the aggregate centred at (-0.5, 1/2, 1/2). Propagation of this N—H···O hydrogen bond thus generates a C33(13)[R66(12)] chain of rings running parallel to the [100] direction; in this chain, the R66(12) rings are centred at (n, 1/2, 1/2) (n = zero or integer), while the diamines linking the R66(12) rings are centred at (n + 1/2, 1/2, 1/2) (n = zero or integer) (Fig. 3). The second H atom of the amino group, H1B, plays no role in the hydrogen bonding.
The pairwise linking of the ferrocenediol molecules into centrosymmetric R66(12) rings by pairs of X—H units, which can act as both donors and acceptors of hydrogen bonds, observed here for X = N, has also been observed in the finite 1:1 adduct formed between the ferrocenediol and methanol, when X = O (Ferguson et al., 1993). The overall ribbon-like structure of (II) has the hydrogen-bonded rings along the centre of the ribbon, with the ferrocenyl and phenyl units on the periphery. This arrangement effectively precludes the formation of any hydrogen bonds, hard or soft, between adjacent chains, and thus possibly accounts for the non-participation in the hydrogen bonding of H1B. In much the same way, in the finite zero-dimensional aggregates formed in the adduct of the ferrocenediol with 1,2-diaminoethane, the polar hydrogen-bonded core of each aggregate is prevented by the lipophilic organic substituents from interaction with the polar cores of adjacent aggregates.
In compound (I), both components of the amine are significantly non-planar (Table 1), and in compound (II), the terminal N—C—C—C fragment of the amine does not adopt the trans-planar conformation observed for the C—C–C—-C fragments (Table 3). The bond lengths and angles show no unexpected features.