Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055407/bh2142sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055407/bh2142Isup2.hkl |
CCDC reference: 672625
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.076
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C13 .. 5.63 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (3) 3.93
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Abuhijleh & Woods (1992); Beer (1992); Beer & Smith (1997); Li et al. (2006); Long (1995); Mammano et al. (1977); Miller & Epstein (1994); Nguyen et al. (1999); Seiler & Dunitz (1979); Takusagawa & Koetzle (1979).
All reagents were commercially available and of analytical grade. Diacetylferrocene (0.54 g, 2 mmol) and carbohydrazide (0.18 g, 2 mmol) were mixed in ethanol (15 ml). Five drops of acetic acid were added and the solution was refluxed for 4 h. Then, the solution was cooled to room temperature. Subsequently the dark-red solid formed was filtered off, washed with ethanol and dried in vacuo (yield: 96%). Analysis calculated for C30H36Fe2N8O4: C 52.60, H 5.26, N 16.36%; found: C 52.44, H 5.24, N 16.26%.
All H atoms bonded to C atoms were positioned geometrically and refined as riding to their carrier atoms, with C—H = 0.96–0.98 Å and Uiso(H) = 1.2Ueq(carrier C) for cyclopentadienyl and Uiso(H) = 1.5Ueq(carrier C) for methyl groups. H atoms for amine groups and water molecule were found in a difference map and refined with free coordinates and Uiso(H) = 1.2Ueq(carrier N) or Uiso(H) = 1.5Ueq(O1W).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), with atom displacement ellipsoids drawn at the 50% probability level. |
[Fe2(C15H16N4O)2]·2H2O | F(000) = 1424 |
Mr = 684.37 | Dx = 1.523 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 398 reflections |
a = 28.708 (4) Å | θ = 1.7–28.1° |
b = 7.9756 (11) Å | µ = 1.02 mm−1 |
c = 15.305 (2) Å | T = 293 K |
β = 121.576 (2)° | Irregular, red |
V = 2985.5 (7) Å3 | 0.20 × 0.18 × 0.16 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2636 independent reflections |
Radiation source: fine-focus sealed tube | 1718 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
0.3° wide ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −22→34 |
Tmin = 0.822, Tmax = 0.853 | k = −9→9 |
7443 measured reflections | l = −18→17 |
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) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0303P)2] where P = (Fo2 + 2Fc2)/3 |
2636 reflections | (Δ/σ)max < 0.001 |
213 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
[Fe2(C15H16N4O)2]·2H2O | V = 2985.5 (7) Å3 |
Mr = 684.37 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 28.708 (4) Å | µ = 1.02 mm−1 |
b = 7.9756 (11) Å | T = 293 K |
c = 15.305 (2) Å | 0.20 × 0.18 × 0.16 mm |
β = 121.576 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 2636 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1718 reflections with I > 2σ(I) |
Tmin = 0.822, Tmax = 0.853 | Rint = 0.070 |
7443 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.38 e Å−3 |
2636 reflections | Δρmin = −0.25 e Å−3 |
213 parameters |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.177935 (16) | 0.15125 (6) | 0.29805 (3) | 0.03626 (15) | |
N1 | 0.05413 (9) | 0.3357 (3) | 0.05970 (17) | 0.0385 (6) | |
O1 | 0.03726 (8) | 0.4466 (3) | −0.12140 (14) | 0.0466 (6) | |
C1 | 0.21068 (14) | 0.0616 (5) | 0.2179 (3) | 0.0588 (10) | |
H1A | 0.2170 | 0.1263 | 0.1706 | 0.071* | |
N2 | 0.00660 (10) | 0.3018 (3) | −0.03320 (19) | 0.0403 (7) | |
H2N | −0.0201 (12) | 0.258 (4) | −0.033 (2) | 0.048* | |
C2 | 0.24803 (13) | 0.0413 (5) | 0.3234 (3) | 0.0577 (10) | |
H2A | 0.2848 | 0.0901 | 0.3624 | 0.069* | |
N3 | −0.04608 (10) | 0.3296 (3) | −0.20789 (18) | 0.0414 (7) | |
H3N | −0.0501 (12) | 0.371 (4) | −0.264 (2) | 0.050* | |
C3 | 0.22351 (12) | −0.0580 (4) | 0.3637 (3) | 0.0498 (9) | |
H3A | 0.2402 | −0.0909 | 0.4357 | 0.060* | |
N4 | −0.08668 (10) | 0.2442 (3) | −0.20452 (18) | 0.0384 (6) | |
C4 | 0.16983 (12) | −0.1025 (4) | 0.2821 (2) | 0.0400 (8) | |
C5 | 0.16302 (13) | −0.0266 (4) | 0.1917 (2) | 0.0477 (9) | |
H5A | 0.1302 | −0.0338 | 0.1229 | 0.057* | |
C6 | 0.12439 (12) | 0.2452 (4) | 0.3353 (2) | 0.0392 (8) | |
H6A | 0.1012 | 0.1788 | 0.3515 | 0.047* | |
C7 | 0.17748 (13) | 0.3007 (4) | 0.4061 (2) | 0.0453 (9) | |
H7A | 0.1977 | 0.2797 | 0.4801 | 0.054* | |
C8 | 0.19695 (13) | 0.3893 (4) | 0.3529 (2) | 0.0473 (9) | |
H8A | 0.2330 | 0.4420 | 0.3833 | 0.057* | |
C9 | 0.15578 (12) | 0.3895 (4) | 0.2476 (2) | 0.0443 (9) | |
H9A | 0.1582 | 0.4430 | 0.1925 | 0.053* | |
C10 | 0.11016 (12) | 0.2996 (4) | 0.2359 (2) | 0.0365 (8) | |
C11 | 0.05932 (12) | 0.2640 (4) | 0.1388 (2) | 0.0356 (7) | |
C12 | 0.01811 (12) | 0.1501 (4) | 0.1399 (2) | 0.0523 (9) | |
H12A | 0.0057 | 0.0696 | 0.0855 | 0.079* | |
H12B | −0.0124 | 0.2151 | 0.1303 | 0.079* | |
H12C | 0.0346 | 0.0928 | 0.2045 | 0.079* | |
C13 | 0.00185 (13) | 0.3665 (4) | −0.1192 (2) | 0.0388 (8) | |
C14 | −0.12873 (13) | 0.1977 (4) | −0.2894 (2) | 0.0400 (8) | |
C15 | −0.13729 (14) | 0.2308 (4) | −0.3935 (2) | 0.0597 (10) | |
H15A | −0.1691 | 0.1713 | −0.4445 | 0.090* | |
H15B | −0.1059 | 0.1935 | −0.3948 | 0.090* | |
H15C | −0.1424 | 0.3489 | −0.4077 | 0.090* | |
O1W | 0.11076 (12) | 0.6713 (4) | 0.03268 (19) | 0.0670 (8) | |
H1WB | 0.1098 (17) | 0.667 (6) | 0.082 (3) | 0.100* | |
H1WA | 0.0909 (16) | 0.601 (5) | −0.007 (3) | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0310 (3) | 0.0420 (3) | 0.0316 (3) | −0.0025 (2) | 0.0135 (2) | −0.0047 (2) |
N1 | 0.0337 (15) | 0.0457 (16) | 0.0271 (14) | −0.0024 (12) | 0.0098 (12) | −0.0014 (13) |
O1 | 0.0437 (14) | 0.0591 (15) | 0.0347 (13) | −0.0169 (12) | 0.0190 (11) | −0.0079 (11) |
C1 | 0.058 (2) | 0.071 (3) | 0.065 (3) | −0.013 (2) | 0.044 (2) | −0.023 (2) |
N2 | 0.0344 (17) | 0.0492 (19) | 0.0279 (14) | −0.0059 (12) | 0.0099 (13) | 0.0005 (13) |
C2 | 0.030 (2) | 0.066 (3) | 0.075 (3) | −0.0046 (18) | 0.027 (2) | −0.025 (2) |
N3 | 0.0398 (16) | 0.0489 (18) | 0.0268 (15) | −0.0068 (14) | 0.0115 (14) | 0.0002 (13) |
C3 | 0.0325 (19) | 0.050 (2) | 0.048 (2) | 0.0086 (16) | 0.0080 (17) | −0.0084 (18) |
N4 | 0.0344 (16) | 0.0410 (16) | 0.0315 (15) | −0.0029 (12) | 0.0115 (13) | −0.0023 (12) |
C4 | 0.038 (2) | 0.036 (2) | 0.036 (2) | 0.0024 (14) | 0.0127 (17) | −0.0087 (14) |
C5 | 0.046 (2) | 0.056 (2) | 0.040 (2) | −0.0061 (17) | 0.0216 (17) | −0.0167 (17) |
C6 | 0.040 (2) | 0.047 (2) | 0.0307 (18) | 0.0049 (15) | 0.0182 (16) | −0.0014 (15) |
C7 | 0.049 (2) | 0.047 (2) | 0.0292 (18) | 0.0089 (16) | 0.0132 (17) | −0.0038 (15) |
C8 | 0.041 (2) | 0.044 (2) | 0.041 (2) | −0.0066 (15) | 0.0112 (17) | −0.0093 (16) |
C9 | 0.042 (2) | 0.044 (2) | 0.0358 (19) | −0.0049 (15) | 0.0128 (16) | 0.0078 (15) |
C10 | 0.038 (2) | 0.041 (2) | 0.0254 (17) | 0.0064 (14) | 0.0130 (15) | 0.0015 (14) |
C11 | 0.0341 (19) | 0.0357 (18) | 0.0328 (18) | 0.0046 (14) | 0.0146 (15) | −0.0004 (15) |
C12 | 0.043 (2) | 0.061 (2) | 0.045 (2) | −0.0050 (18) | 0.0174 (17) | 0.0080 (18) |
C13 | 0.043 (2) | 0.037 (2) | 0.0298 (18) | 0.0005 (16) | 0.0144 (16) | −0.0053 (15) |
C14 | 0.039 (2) | 0.0340 (19) | 0.0343 (19) | 0.0040 (14) | 0.0104 (16) | −0.0012 (14) |
C15 | 0.059 (2) | 0.063 (3) | 0.038 (2) | −0.0139 (19) | 0.0119 (18) | −0.0026 (18) |
O1W | 0.0757 (19) | 0.076 (2) | 0.0496 (18) | −0.0255 (14) | 0.0330 (16) | −0.0168 (15) |
Fe1—C9 | 2.024 (3) | N4—C14 | 1.280 (3) |
Fe1—C1 | 2.026 (3) | C4—C5 | 1.426 (4) |
Fe1—C5 | 2.028 (3) | C4—C14i | 1.456 (4) |
Fe1—C8 | 2.032 (3) | C5—H5A | 0.9800 |
Fe1—C3 | 2.032 (3) | C6—C7 | 1.401 (4) |
Fe1—C4 | 2.037 (3) | C6—C10 | 1.421 (4) |
Fe1—C2 | 2.037 (3) | C6—H6A | 0.9800 |
Fe1—C10 | 2.038 (3) | C7—C8 | 1.396 (4) |
Fe1—C6 | 2.042 (3) | C7—H7A | 0.9800 |
Fe1—C7 | 2.043 (3) | C8—C9 | 1.414 (4) |
N1—C11 | 1.275 (3) | C8—H8A | 0.9800 |
N1—N2 | 1.387 (3) | C9—C10 | 1.419 (4) |
O1—C13 | 1.216 (3) | C9—H9A | 0.9800 |
C1—C5 | 1.397 (4) | C10—C11 | 1.465 (4) |
C1—C2 | 1.403 (4) | C11—C12 | 1.498 (4) |
C1—H1A | 0.9800 | C12—H12A | 0.9600 |
N2—C13 | 1.352 (4) | C12—H12B | 0.9600 |
N2—H2N | 0.84 (3) | C12—H12C | 0.9600 |
C2—C3 | 1.399 (5) | C14—C4i | 1.456 (4) |
C2—H2A | 0.9800 | C14—C15 | 1.503 (4) |
N3—C13 | 1.366 (4) | C15—H15A | 0.9600 |
N3—N4 | 1.374 (3) | C15—H15B | 0.9600 |
N3—H3N | 0.87 (3) | C15—H15C | 0.9600 |
C3—C4 | 1.430 (4) | O1W—H1WB | 0.78 (4) |
C3—H3A | 0.9800 | O1W—H1WA | 0.80 (4) |
C9—Fe1—C1 | 104.65 (14) | C4—C3—H3A | 125.8 |
C9—Fe1—C5 | 117.27 (13) | Fe1—C3—H3A | 125.8 |
C1—Fe1—C5 | 40.32 (12) | C14—N4—N3 | 118.2 (3) |
C9—Fe1—C8 | 40.82 (11) | C5—C4—C3 | 106.2 (3) |
C1—Fe1—C8 | 118.07 (14) | C5—C4—C14i | 126.2 (3) |
C5—Fe1—C8 | 152.04 (14) | C3—C4—C14i | 127.5 (3) |
C9—Fe1—C3 | 162.16 (13) | C5—C4—Fe1 | 69.12 (18) |
C1—Fe1—C3 | 68.09 (15) | C3—C4—Fe1 | 69.24 (17) |
C5—Fe1—C3 | 68.48 (13) | C14i—C4—Fe1 | 123.7 (2) |
C8—Fe1—C3 | 126.80 (13) | C1—C5—C4 | 108.6 (3) |
C9—Fe1—C4 | 153.31 (12) | C1—C5—Fe1 | 69.78 (18) |
C1—Fe1—C4 | 68.71 (14) | C4—C5—Fe1 | 69.81 (17) |
C5—Fe1—C4 | 41.07 (12) | C1—C5—H5A | 125.7 |
C8—Fe1—C4 | 165.25 (12) | C4—C5—H5A | 125.7 |
C3—Fe1—C4 | 41.15 (11) | Fe1—C5—H5A | 125.7 |
C9—Fe1—C2 | 123.95 (15) | C7—C6—C10 | 108.5 (3) |
C1—Fe1—C2 | 40.40 (13) | C7—C6—Fe1 | 70.02 (18) |
C5—Fe1—C2 | 67.93 (13) | C10—C6—Fe1 | 69.47 (17) |
C8—Fe1—C2 | 107.38 (14) | C7—C6—H6A | 125.7 |
C3—Fe1—C2 | 40.22 (13) | C10—C6—H6A | 125.7 |
C4—Fe1—C2 | 68.56 (13) | Fe1—C6—H6A | 125.7 |
C9—Fe1—C10 | 40.91 (12) | C8—C7—C6 | 108.3 (3) |
C1—Fe1—C10 | 123.67 (14) | C8—C7—Fe1 | 69.50 (18) |
C5—Fe1—C10 | 106.42 (12) | C6—C7—Fe1 | 69.87 (17) |
C8—Fe1—C10 | 68.56 (12) | C8—C7—H7A | 125.8 |
C3—Fe1—C10 | 156.62 (13) | C6—C7—H7A | 125.8 |
C4—Fe1—C10 | 119.98 (12) | Fe1—C7—H7A | 125.8 |
C2—Fe1—C10 | 160.94 (14) | C7—C8—C9 | 108.3 (3) |
C9—Fe1—C6 | 68.27 (13) | C7—C8—Fe1 | 70.42 (18) |
C1—Fe1—C6 | 162.62 (13) | C9—C8—Fe1 | 69.30 (17) |
C5—Fe1—C6 | 127.40 (13) | C7—C8—H8A | 125.8 |
C8—Fe1—C6 | 67.67 (13) | C9—C8—H8A | 125.8 |
C3—Fe1—C6 | 123.19 (14) | Fe1—C8—H8A | 125.8 |
C4—Fe1—C6 | 110.05 (13) | C8—C9—C10 | 108.0 (3) |
C2—Fe1—C6 | 156.61 (13) | C8—C9—Fe1 | 69.88 (17) |
C10—Fe1—C6 | 40.78 (11) | C10—C9—Fe1 | 70.08 (17) |
C9—Fe1—C7 | 68.12 (13) | C8—C9—H9A | 126.0 |
C1—Fe1—C7 | 153.75 (14) | C10—C9—H9A | 126.0 |
C5—Fe1—C7 | 165.66 (14) | Fe1—C9—H9A | 126.0 |
C8—Fe1—C7 | 40.08 (12) | C9—C10—C6 | 106.9 (3) |
C3—Fe1—C7 | 110.74 (13) | C9—C10—C11 | 126.1 (3) |
C4—Fe1—C7 | 128.88 (13) | C6—C10—C11 | 127.0 (3) |
C2—Fe1—C7 | 121.40 (13) | C9—C10—Fe1 | 69.02 (17) |
C10—Fe1—C7 | 68.29 (12) | C6—C10—Fe1 | 69.75 (16) |
C6—Fe1—C7 | 40.11 (11) | C11—C10—Fe1 | 124.1 (2) |
C11—N1—N2 | 116.7 (3) | N1—C11—C10 | 115.8 (3) |
C5—C1—C2 | 108.4 (3) | N1—C11—C12 | 125.6 (3) |
C5—C1—Fe1 | 69.90 (18) | C10—C11—C12 | 118.7 (3) |
C2—C1—Fe1 | 70.23 (19) | C11—C12—H12A | 109.5 |
C5—C1—H1A | 125.8 | C11—C12—H12B | 109.5 |
C2—C1—H1A | 125.8 | H12A—C12—H12B | 109.5 |
Fe1—C1—H1A | 125.8 | C11—C12—H12C | 109.5 |
C13—N2—N1 | 117.8 (3) | H12A—C12—H12C | 109.5 |
C13—N2—H2N | 122 (2) | H12B—C12—H12C | 109.5 |
N1—N2—H2N | 119 (2) | O1—C13—N2 | 124.6 (3) |
C3—C2—C1 | 108.4 (3) | O1—C13—N3 | 120.5 (3) |
C3—C2—Fe1 | 69.70 (18) | N2—C13—N3 | 114.9 (3) |
C1—C2—Fe1 | 69.38 (19) | N4—C14—C4i | 116.4 (3) |
C3—C2—H2A | 125.8 | N4—C14—C15 | 124.6 (3) |
C1—C2—H2A | 125.8 | C4i—C14—C15 | 118.9 (3) |
Fe1—C2—H2A | 125.8 | C14—C15—H15A | 109.5 |
C13—N3—N4 | 120.1 (3) | C14—C15—H15B | 109.5 |
C13—N3—H3N | 116 (2) | H15A—C15—H15B | 109.5 |
N4—N3—H3N | 123 (2) | C14—C15—H15C | 109.5 |
C2—C3—C4 | 108.4 (3) | H15A—C15—H15C | 109.5 |
C2—C3—Fe1 | 70.1 (2) | H15B—C15—H15C | 109.5 |
C4—C3—Fe1 | 69.61 (17) | H1WB—O1W—H1WA | 109 (4) |
C2—C3—H3A | 125.8 |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N4 | 0.84 (3) | 2.30 (3) | 2.628 (3) | 104 (2) |
N3—H3N···O1ii | 0.87 (3) | 2.06 (3) | 2.908 (3) | 164 (3) |
O1W—H1WA···O1 | 0.80 (4) | 2.04 (4) | 2.831 (3) | 172 (4) |
O1W—H1WB···N4iii | 0.78 (4) | 2.39 (4) | 3.123 (4) | 156 (4) |
Symmetry codes: (ii) −x, y, −z−1/2; (iii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Fe2(C15H16N4O)2]·2H2O |
Mr | 684.37 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 28.708 (4), 7.9756 (11), 15.305 (2) |
β (°) | 121.576 (2) |
V (Å3) | 2985.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.02 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.822, 0.853 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7443, 2636, 1718 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.076, 0.81 |
No. of reflections | 2636 |
No. of parameters | 213 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.25 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N4 | 0.84 (3) | 2.30 (3) | 2.628 (3) | 104 (2) |
N3—H3N···O1i | 0.87 (3) | 2.06 (3) | 2.908 (3) | 164 (3) |
O1W—H1WA···O1 | 0.80 (4) | 2.04 (4) | 2.831 (3) | 172 (4) |
O1W—H1WB···N4ii | 0.78 (4) | 2.39 (4) | 3.123 (4) | 156 (4) |
Symmetry codes: (i) −x, y, −z−1/2; (ii) −x, −y+1, −z. |
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Much attention has been paid to the chemistry of ferrocene complexes because of their potential applications in material sciences, such as molecular sensors (Beer, 1992; Beer & Smith, 1997), molecular magnetic devices (Miller & Epstein, 1994) and nonlinear optical materials (Nguyen et al., 1999; Long, 1995). In continuation of our research work in the assembly and properties of ferrocene-containing Schiff base compounds (Li et al., 2006), we report here the crystal structure analysis of a bis-ferrocene Schiff base compound, (I).
The compound is a cyclic bis-ferrocene complex lying on an inversion centre. The asymmetric unit is completed with a lattice water molecule. The Fe—Cring bond lengths range from 2.024 (3) to 2.043 (3) Å (average: 2.034 Å) and are within the expected range (Seiler & Dunitz, 1979; Mammano et al., 1977). The average intra C≐C bond length and C≐ C≐C angle in cyclopentadienyl groups are 1.411 Å and 108°, which are similar to dimensions reported in the literature (Abuhijleh & Woods, 1992; Takusagawa & Koetzle, 1979). The cyclopentadienyl rings in each ferrocenyl fragment are planar and nearly parallel, with a dihedral angle of 3.7 ° at Fe1. The bond lengths N1—C11 and N4—C14 are within the normal range for C═N double bonds, while the N2—C13 and N3—C13 bond lengths suggest that they are single N—C bonds. In addition, the bond length C13═O1 is 1.216 (3) Å, consistent with a carbonyl functionality. Moreover, N1—N2 and N3—N4 bond distances are within the normal range for N—N single bonds. The two side chains are parallel by symmetry, with a torsion angle C11—C10···C4—C14i of about -61.6 ° [symmetry code: (i) -x, -y, -z].
In the crystal structure, molecules are connected by four different kinds of intra- and intermolecular hydrogen bonds. Besides the intramolecular N2—H2N···N4 and the intermolecular N3—H3N···O1ii interaction present in the ligand [symmetry code: (ii) -x, y, -z - 1/2], there are two hydrogen bonds involving the water molecule.