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The title complex, [Fe(C19H27N10)](ClO4)3·2H2O, is a new polymorph of an iron(II) Schiff base complex of tris­(2-amino­ethyl)methyl­ammonium with imidazole-2-carboxaldehyde. The octa­hedral FeII atom is bound to three facial imidazole N atoms with average Fe-Nimidazole and Fe-Nimine bond distances of 1.963 (5) and 1.951 (5) Å, respectively. The central N atom of the tripodal ligand is outside the bonding distance at 3.92 Å. The crystal packing is stabilized by the hydrogen-bonding inter­actions between the two water mol­ecules (acceptor) and two of the three imidazole NH groups (donor). The third imidazole NH group (donor) forms a hydrogen bond to one of the three perchlorate counter-ions (acceptor).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061673/tk2214sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061673/tk2214Isup2.hkl
Contains datablock I

CCDC reference: 630724

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.108
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1W1 .. H3BB .. 1.94 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1W1 ... ? PLAT432_ALERT_2_B Short Inter X...Y Contact O23 .. C3A .. 2.86 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact O33 .. C3B .. 2.89 Ang.
Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl3 PLAT432_ALERT_2_C Short Inter X...Y Contact O23 .. C .. 3.01 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 31 PLAT731_ALERT_1_C Bond Calc 0.87(4), Rep 0.866(19) ...... 2.11 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.80(5), Rep 0.807(19) ...... 2.63 su-Ra O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.80(5), Rep 0.807(19) ...... 2.63 su-Ra O1W -H2# 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Iron(II) and iron(III) Schiff base complexes of tris(2-aminoethyl)amine (tren) with imidazole carboxaldehyde have displayed spin crossover behavior (Brewer et al., 2006). Further, it has been demonstrated that the distance between the Fe atom and the central tren-N atom, Nap, is an indicator of spin-state (Brewer et al., 2006). Shorter distances correlate with high spin and longer distances with low spin. Quarternization of Nap, as observed in the title complex, (I), results in an elongated Fe—Nap distance due to both the conformation of the Nap atom (inverted away from the Fe atom) and the repulsive forces between the positively charged atoms (Brewer et al., 2005). Recently, it was shown that (I), without the methyl group on Nap, could serve as a bidentate hydrogen bond donor to the perchlorate anion of potassium perchlorate using the adjacent imidazole-NH and imine-CH H atoms to give supramolecular complexes (Brewer et al., 2007). Since the present molecule possesses this same structural feature, the reaction of it with potassium perchlorate was investigated. The reaction did not yield the desired product but gave (I) as a polymorph (Brewer et al., 2007). The structure of the iron cation differs from the original report in that the three arms of the ligand are not identical. In addition, the hydrogen bonding interactions with coordinated water and perchlorate are significantly different. Investigation of these effects on the spin crossover process and reactivity of the complex will be aided by the structural characterization of this new polymorph. In view of the importance of the spin crossover phenomenom and supramolecular systems, the present paper reports the crystal structure of (I) (Fig. 1).

The octahedral iron(II) atom is bound to three facial imidazole-N atoms whose average Fe–N bond distances for the imidazole- and imine-N atoms are 1.963 (5)Å and 1.951 (5) Å, respectively. The central N atom of the tripodal ligand is outside the bonding distance at 3.92 Å. Crystal packing is stabilized by the hydrogen bonding interactions between the two water molecules (acceptor) and two of the three imidazole NH groups (donor). The third imidazole NH group (donor) hydrogen bonds to one of the three perchlorate counterions (acceptor) (Table 1 & Fig. 2).

Related literature top

For the synthesis, see: Brewer et al. (2005). For related structures, see: Brewer et al. (2006, 2007).

Experimental top

Complex (I) was synthesized as previously described (Brewer et al., 2005) and was recrystallized from methanol solution in the presence of equimolal potassium perchlorate. The resulting crystals were analyzed by X-ray diffraction.

Refinement top

The positional parameters of the water-bound H atoms were refined with Uiso(H) = 1.17–1.49Ueq(C,N); see Table 1 for distances. The remaining H atoms were included in the riding model approximation with N—H = 0.88Å and C—H = 0.95 to 0.99 Å, and with Uiso(H) = 1.17–1.49Ueq(C,N).

Structure description top

Iron(II) and iron(III) Schiff base complexes of tris(2-aminoethyl)amine (tren) with imidazole carboxaldehyde have displayed spin crossover behavior (Brewer et al., 2006). Further, it has been demonstrated that the distance between the Fe atom and the central tren-N atom, Nap, is an indicator of spin-state (Brewer et al., 2006). Shorter distances correlate with high spin and longer distances with low spin. Quarternization of Nap, as observed in the title complex, (I), results in an elongated Fe—Nap distance due to both the conformation of the Nap atom (inverted away from the Fe atom) and the repulsive forces between the positively charged atoms (Brewer et al., 2005). Recently, it was shown that (I), without the methyl group on Nap, could serve as a bidentate hydrogen bond donor to the perchlorate anion of potassium perchlorate using the adjacent imidazole-NH and imine-CH H atoms to give supramolecular complexes (Brewer et al., 2007). Since the present molecule possesses this same structural feature, the reaction of it with potassium perchlorate was investigated. The reaction did not yield the desired product but gave (I) as a polymorph (Brewer et al., 2007). The structure of the iron cation differs from the original report in that the three arms of the ligand are not identical. In addition, the hydrogen bonding interactions with coordinated water and perchlorate are significantly different. Investigation of these effects on the spin crossover process and reactivity of the complex will be aided by the structural characterization of this new polymorph. In view of the importance of the spin crossover phenomenom and supramolecular systems, the present paper reports the crystal structure of (I) (Fig. 1).

The octahedral iron(II) atom is bound to three facial imidazole-N atoms whose average Fe–N bond distances for the imidazole- and imine-N atoms are 1.963 (5)Å and 1.951 (5) Å, respectively. The central N atom of the tripodal ligand is outside the bonding distance at 3.92 Å. Crystal packing is stabilized by the hydrogen bonding interactions between the two water molecules (acceptor) and two of the three imidazole NH groups (donor). The third imidazole NH group (donor) hydrogen bonds to one of the three perchlorate counterions (acceptor) (Table 1 & Fig. 2).

For the synthesis, see: Brewer et al. (2005). For related structures, see: Brewer et al. (2006, 2007).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of the cation in (I), showing atom labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Partial packing diagram for (I), viewed down the b axis. Dashed lines indicate C–H···O (water & perchlorate) hydrogen bonds.
{Tris[2-(imidazol-2-ylmethylimino)ethyl]methylammonium}iron(II) tris(perchlorate) dihydrate top
Crystal data top
[Fe(C19H27N10)](ClO4)3·2H2OF(000) = 3232
Mr = 785.74Dx = 1.707 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9963 reflections
a = 13.9630 (18) Åθ = 2.2–28.9°
b = 11.7810 (15) ŵ = 0.84 mm1
c = 37.182 (5) ÅT = 173 K
V = 6116.4 (14) Å3Chunk, dark-red
Z = 80.54 × 0.45 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8324 independent reflections
Radiation source: fine-focus sealed tube6601 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 29.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.682, Tmax = 0.904k = 1613
65065 measured reflectionsl = 5151
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0471P)2 + 5.7069P]
where P = (Fo2 + 2Fc2)/3
8324 reflections(Δ/σ)max = 0.001
436 parametersΔρmax = 0.76 e Å3
6 restraintsΔρmin = 0.62 e Å3
Crystal data top
[Fe(C19H27N10)](ClO4)3·2H2OV = 6116.4 (14) Å3
Mr = 785.74Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.9630 (18) ŵ = 0.84 mm1
b = 11.7810 (15) ÅT = 173 K
c = 37.182 (5) Å0.54 × 0.45 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8324 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6601 reflections with I > 2σ(I)
Tmin = 0.682, Tmax = 0.904Rint = 0.054
65065 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0416 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.76 e Å3
8324 reflectionsΔρmin = 0.62 e Å3
436 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe0.542493 (19)0.51159 (2)0.110991 (7)0.01627 (7)
Cl10.32256 (4)0.00301 (5)0.015096 (15)0.02982 (12)
Cl20.24581 (4)0.63667 (5)0.208500 (15)0.02861 (12)
Cl30.57715 (4)0.00513 (5)0.181644 (16)0.03151 (13)
O110.3162 (2)0.0909 (2)0.01088 (7)0.0756 (8)
O120.23275 (13)0.05400 (18)0.01888 (6)0.0489 (5)
O130.39474 (14)0.07620 (18)0.00529 (6)0.0526 (5)
O140.34756 (14)0.05377 (19)0.04951 (5)0.0494 (5)
O210.23376 (18)0.51820 (17)0.21519 (7)0.0598 (6)
O220.19608 (18)0.6630 (2)0.17533 (6)0.0610 (6)
O230.34507 (13)0.66157 (19)0.20374 (6)0.0505 (5)
O240.20629 (13)0.70357 (17)0.23716 (5)0.0437 (5)
O310.50024 (19)0.0216 (2)0.15709 (7)0.0687 (7)
O320.61507 (15)0.10022 (17)0.19422 (8)0.0617 (6)
O330.65127 (16)0.06867 (16)0.16416 (7)0.0570 (6)
O340.53883 (17)0.06912 (18)0.21060 (6)0.0576 (6)
O1W0.96601 (19)0.4969 (3)0.08139 (9)0.1023 (13)
H1W10.983 (4)0.562 (3)0.0904 (16)0.153*
H1W21.003 (4)0.489 (5)0.0650 (12)0.153*
O2W0.28606 (16)0.98531 (17)0.12333 (6)0.0461 (5)
H2W10.287 (3)1.024 (3)0.1051 (6)0.069*
H2W20.304 (3)1.029 (3)0.1392 (7)0.069*
N0.56728 (13)0.38916 (15)0.20854 (4)0.0215 (3)
N1A0.54566 (12)0.61049 (14)0.15322 (4)0.0190 (3)
N2A0.44316 (12)0.61938 (14)0.09684 (5)0.0199 (3)
N3A0.36892 (13)0.78081 (16)0.10830 (5)0.0269 (4)
H3AB0.35170.84400.11920.032*
N1B0.65376 (12)0.42147 (14)0.12542 (4)0.0193 (3)
N2B0.64328 (12)0.60169 (14)0.08733 (4)0.0198 (3)
N3B0.79608 (13)0.61176 (17)0.07239 (5)0.0288 (4)
H3BB0.85730.59470.07070.035*
N1C0.45107 (12)0.40472 (14)0.13101 (4)0.0192 (3)
N2C0.52259 (12)0.41612 (14)0.06825 (4)0.0198 (3)
N3C0.44957 (15)0.26827 (17)0.04444 (5)0.0304 (4)
H3CB0.41210.20860.04220.036*
C0.57789 (18)0.3404 (2)0.24639 (6)0.0301 (5)
H0A0.57690.25730.24520.045*
H0B0.52480.36690.26150.045*
H0C0.63880.36560.25680.045*
C1A0.56992 (16)0.51802 (17)0.21406 (5)0.0236 (4)
H1AA0.50370.54270.21950.028*
H1AB0.60840.53270.23590.028*
C2A0.60808 (15)0.59560 (17)0.18461 (5)0.0220 (4)
H2AA0.62050.67120.19520.026*
H2AB0.67020.56500.17620.026*
C3A0.49249 (15)0.69994 (17)0.15189 (5)0.0214 (4)
H3AA0.49210.75670.17010.026*
C4A0.43400 (14)0.70505 (17)0.12017 (5)0.0209 (4)
C5A0.33456 (16)0.7412 (2)0.07621 (6)0.0301 (5)
H5AA0.28750.77640.06150.036*
C6A0.38088 (15)0.64128 (19)0.06928 (6)0.0258 (4)
H6AA0.37140.59470.04870.031*
C1B0.65416 (15)0.34079 (18)0.18863 (6)0.0238 (4)
H1BA0.70860.39240.19340.029*
H1BB0.67000.26740.20010.029*
C2B0.65151 (15)0.32028 (17)0.14818 (5)0.0221 (4)
H2BA0.70680.27180.14170.026*
H2BB0.59260.27710.14250.026*
C3B0.73460 (15)0.45056 (18)0.11120 (5)0.0221 (4)
H3BA0.79220.40880.11440.027*
C4B0.72866 (14)0.55230 (18)0.09009 (5)0.0219 (4)
C5B0.65706 (16)0.69750 (18)0.06694 (6)0.0243 (4)
H5BA0.60890.75070.06050.029*
C6B0.75165 (17)0.7035 (2)0.05749 (6)0.0300 (5)
H6BA0.78090.76090.04330.036*
C1C0.47042 (15)0.34435 (18)0.19572 (6)0.0233 (4)
H1CA0.48110.26700.18610.028*
H1CB0.42910.33630.21720.028*
C2C0.41328 (14)0.40958 (18)0.16763 (5)0.0217 (4)
H2CA0.34700.37970.16740.026*
H2CB0.41000.49010.17510.026*
C3C0.41876 (15)0.32709 (18)0.10959 (6)0.0243 (4)
H3CA0.37230.27230.11650.029*
C4C0.46053 (15)0.33235 (18)0.07423 (6)0.0244 (4)
C5C0.55206 (15)0.40500 (19)0.03331 (6)0.0245 (4)
H5CA0.59640.45330.02140.029*
C6C0.50736 (18)0.3132 (2)0.01838 (6)0.0310 (5)
H6CA0.51500.28580.00550.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.01808 (13)0.01279 (13)0.01794 (13)0.00035 (10)0.00077 (10)0.00083 (10)
Cl10.0326 (3)0.0217 (3)0.0352 (3)0.0011 (2)0.0064 (2)0.0012 (2)
Cl20.0264 (2)0.0239 (3)0.0356 (3)0.00118 (19)0.0062 (2)0.0030 (2)
Cl30.0313 (3)0.0234 (3)0.0399 (3)0.0000 (2)0.0070 (2)0.0013 (2)
O110.118 (2)0.0463 (14)0.0629 (15)0.0105 (14)0.0153 (15)0.0256 (12)
O120.0305 (9)0.0428 (11)0.0734 (14)0.0057 (8)0.0084 (9)0.0190 (10)
O130.0387 (11)0.0425 (12)0.0765 (15)0.0111 (9)0.0060 (10)0.0037 (10)
O140.0471 (11)0.0592 (13)0.0418 (11)0.0193 (10)0.0031 (9)0.0152 (10)
O210.0761 (16)0.0259 (10)0.0775 (16)0.0005 (10)0.0343 (13)0.0033 (10)
O220.0761 (16)0.0557 (14)0.0512 (12)0.0259 (12)0.0215 (11)0.0124 (10)
O230.0311 (9)0.0589 (13)0.0615 (13)0.0122 (9)0.0157 (9)0.0303 (10)
O240.0441 (10)0.0425 (11)0.0447 (10)0.0049 (9)0.0181 (8)0.0097 (8)
O310.0615 (15)0.0787 (18)0.0660 (16)0.0064 (13)0.0182 (12)0.0026 (13)
O320.0452 (12)0.0272 (10)0.113 (2)0.0029 (9)0.0029 (12)0.0131 (11)
O330.0592 (13)0.0294 (10)0.0824 (16)0.0085 (9)0.0369 (12)0.0004 (10)
O340.0787 (16)0.0403 (12)0.0538 (13)0.0004 (11)0.0307 (11)0.0083 (10)
O1W0.0430 (14)0.185 (4)0.079 (2)0.0426 (19)0.0211 (13)0.056 (2)
O2W0.0545 (12)0.0397 (11)0.0442 (11)0.0104 (10)0.0002 (10)0.0089 (9)
N0.0263 (8)0.0185 (8)0.0196 (8)0.0007 (7)0.0005 (7)0.0020 (6)
N1A0.0221 (8)0.0159 (8)0.0190 (8)0.0029 (6)0.0008 (6)0.0002 (6)
N2A0.0207 (8)0.0163 (8)0.0227 (8)0.0005 (6)0.0009 (6)0.0007 (6)
N3A0.0275 (9)0.0192 (9)0.0340 (10)0.0054 (7)0.0034 (8)0.0025 (7)
N1B0.0221 (8)0.0155 (8)0.0203 (8)0.0013 (6)0.0020 (6)0.0021 (6)
N2B0.0230 (8)0.0168 (8)0.0195 (8)0.0023 (6)0.0008 (6)0.0013 (6)
N3B0.0237 (9)0.0324 (10)0.0304 (9)0.0048 (8)0.0048 (7)0.0049 (8)
N1C0.0198 (8)0.0161 (8)0.0218 (8)0.0002 (6)0.0013 (6)0.0000 (6)
N2C0.0227 (8)0.0158 (8)0.0209 (8)0.0024 (6)0.0001 (6)0.0013 (6)
N3C0.0373 (10)0.0250 (10)0.0288 (9)0.0055 (8)0.0040 (8)0.0109 (8)
C0.0424 (13)0.0268 (11)0.0212 (10)0.0012 (10)0.0011 (9)0.0066 (8)
C1A0.0323 (10)0.0193 (10)0.0193 (9)0.0004 (8)0.0019 (8)0.0014 (7)
C2A0.0267 (10)0.0177 (9)0.0217 (9)0.0037 (8)0.0044 (8)0.0026 (7)
C3A0.0268 (10)0.0150 (9)0.0224 (9)0.0010 (7)0.0047 (8)0.0023 (7)
C4A0.0212 (9)0.0170 (9)0.0243 (10)0.0005 (7)0.0040 (7)0.0015 (7)
C5A0.0277 (11)0.0297 (12)0.0329 (12)0.0038 (9)0.0022 (9)0.0069 (9)
C6A0.0246 (10)0.0276 (11)0.0251 (10)0.0010 (8)0.0022 (8)0.0025 (8)
C1B0.0246 (10)0.0214 (10)0.0254 (10)0.0031 (8)0.0014 (8)0.0038 (8)
C2B0.0254 (10)0.0163 (9)0.0245 (10)0.0025 (8)0.0021 (8)0.0021 (7)
C3B0.0213 (9)0.0220 (10)0.0231 (9)0.0014 (8)0.0009 (8)0.0022 (8)
C4B0.0218 (9)0.0231 (10)0.0209 (9)0.0026 (8)0.0033 (7)0.0012 (8)
C5B0.0301 (10)0.0191 (10)0.0236 (10)0.0033 (8)0.0012 (8)0.0022 (8)
C6B0.0344 (12)0.0275 (12)0.0279 (10)0.0087 (9)0.0032 (9)0.0049 (9)
C1C0.0250 (10)0.0211 (10)0.0238 (10)0.0045 (8)0.0026 (8)0.0025 (8)
C2C0.0199 (9)0.0213 (10)0.0241 (10)0.0008 (8)0.0039 (8)0.0003 (8)
C3C0.0240 (10)0.0195 (10)0.0293 (10)0.0046 (8)0.0004 (8)0.0019 (8)
C4C0.0273 (10)0.0197 (10)0.0261 (10)0.0011 (8)0.0039 (8)0.0056 (8)
C5C0.0292 (10)0.0229 (10)0.0213 (9)0.0046 (8)0.0007 (8)0.0019 (8)
C6C0.0384 (12)0.0309 (12)0.0236 (10)0.0044 (10)0.0027 (9)0.0080 (9)
Geometric parameters (Å, º) top
Fe—N1C1.9414 (17)N1C—C3C1.294 (3)
Fe—N2A1.9528 (17)N1C—C2C1.461 (3)
Fe—N1A1.9559 (17)N2C—C4C1.332 (3)
Fe—N1B1.9567 (17)N2C—C5C1.369 (3)
Fe—N2C1.9665 (17)N3C—C4C1.349 (3)
Fe—N2B1.9701 (17)N3C—C6C1.368 (3)
Cl1—O111.418 (2)N3C—H3CB0.8800
Cl1—O131.421 (2)C—H0A0.9800
Cl1—O121.4295 (19)C—H0B0.9800
Cl1—O141.4548 (19)C—H0C0.9800
Cl2—O231.4277 (18)C1A—C2A1.523 (3)
Cl2—O211.428 (2)C1A—H1AA0.9900
Cl2—O241.4357 (18)C1A—H1AB0.9900
Cl2—O221.449 (2)C2A—H2AA0.9900
Cl3—O341.419 (2)C2A—H2AB0.9900
Cl3—O321.428 (2)C3A—C4A1.436 (3)
Cl3—O331.4330 (19)C3A—H3AA0.9500
Cl3—O311.444 (2)C5A—C6A1.368 (3)
O1W—H1W10.866 (19)C5A—H5AA0.9500
O1W—H1W20.807 (19)C6A—H6AA0.9500
O2W—H2W10.820 (17)C1B—C2B1.524 (3)
O2W—H2W20.821 (18)C1B—H1BA0.9900
N—C1.527 (3)C1B—H1BB0.9900
N—C1C1.528 (3)C2B—H2BA0.9900
N—C1B1.531 (3)C2B—H2BB0.9900
N—C1A1.532 (3)C3B—C4B1.435 (3)
N1A—C3A1.290 (3)C3B—H3BA0.9500
N1A—C2A1.467 (2)C5B—C6B1.369 (3)
N2A—C4A1.337 (3)C5B—H5BA0.9500
N2A—C6A1.368 (3)C6B—H6BA0.9500
N3A—C4A1.348 (3)C1C—C2C1.523 (3)
N3A—C5A1.368 (3)C1C—H1CA0.9900
N3A—H3AB0.8800C1C—H1CB0.9900
N1B—C3B1.293 (3)C2C—H2CA0.9900
N1B—C2B1.462 (3)C2C—H2CB0.9900
N2B—C4B1.330 (3)C3C—C4C1.440 (3)
N2B—C5B1.373 (3)C3C—H3CA0.9500
N3B—C4B1.345 (3)C5C—C6C1.367 (3)
N3B—C6B1.364 (3)C5C—H5CA0.9500
N3B—H3BB0.8800C6C—H6CA0.9500
N1C—Fe—N2A93.33 (7)H0B—C—H0C109.5
N1C—Fe—N1A95.36 (7)C2A—C1A—N120.44 (17)
N2A—Fe—N1A81.09 (7)C2A—C1A—H1AA107.2
N1C—Fe—N1B93.73 (7)N—C1A—H1AA107.2
N2A—Fe—N1B172.17 (7)C2A—C1A—H1AB107.2
N1A—Fe—N1B94.88 (7)N—C1A—H1AB107.2
N1C—Fe—N2C81.14 (7)H1AA—C1A—H1AB106.8
N2A—Fe—N2C93.08 (7)N1A—C2A—C1A115.85 (17)
N1A—Fe—N2C173.05 (7)N1A—C2A—H2AA108.3
N1B—Fe—N2C91.34 (7)C1A—C2A—H2AA108.3
N1C—Fe—N2B172.05 (7)N1A—C2A—H2AB108.3
N2A—Fe—N2B92.10 (7)C1A—C2A—H2AB108.3
N1A—Fe—N2B91.22 (7)H2AA—C2A—H2AB107.4
N1B—Fe—N2B81.23 (7)N1A—C3A—C4A113.15 (18)
N2C—Fe—N2B92.77 (7)N1A—C3A—H3AA123.4
O11—Cl1—O13110.43 (16)C4A—C3A—H3AA123.4
O11—Cl1—O12110.79 (16)N2A—C4A—N3A110.61 (18)
O13—Cl1—O12109.80 (12)N2A—C4A—C3A116.54 (18)
O11—Cl1—O14108.29 (15)N3A—C4A—C3A132.85 (19)
O13—Cl1—O14108.99 (13)C6A—C5A—N3A106.98 (19)
O12—Cl1—O14108.48 (12)C6A—C5A—H5AA126.5
O23—Cl2—O21109.69 (14)N3A—C5A—H5AA126.5
O23—Cl2—O24110.63 (11)C5A—C6A—N2A108.8 (2)
O21—Cl2—O24111.22 (13)C5A—C6A—H6AA125.6
O23—Cl2—O22108.41 (15)N2A—C6A—H6AA125.6
O21—Cl2—O22107.53 (15)C2B—C1B—N121.13 (17)
O24—Cl2—O22109.27 (13)C2B—C1B—H1BA107.0
O34—Cl3—O32110.68 (15)N—C1B—H1BA107.0
O34—Cl3—O33109.81 (13)C2B—C1B—H1BB107.0
O32—Cl3—O33109.56 (13)N—C1B—H1BB107.0
O34—Cl3—O31108.37 (16)H1BA—C1B—H1BB106.8
O32—Cl3—O31107.02 (15)N1B—C2B—C1B116.20 (17)
O33—Cl3—O31111.37 (16)N1B—C2B—H2BA108.2
H1W1—O1W—H1W2103 (3)C1B—C2B—H2BA108.2
H2W1—O2W—H2W2104 (2)N1B—C2B—H2BB108.2
C—N—C1C104.07 (16)C1B—C2B—H2BB108.2
C—N—C1B103.21 (16)H2BA—C2B—H2BB107.4
C1C—N—C1B114.95 (16)N1B—C3B—C4B113.24 (18)
C—N—C1A104.30 (16)N1B—C3B—H3BA123.4
C1C—N—C1A113.92 (16)C4B—C3B—H3BA123.4
C1B—N—C1A114.49 (16)N2B—C4B—N3B111.19 (19)
C3A—N1A—C2A118.04 (17)N2B—C4B—C3B117.34 (18)
C3A—N1A—Fe116.28 (14)N3B—C4B—C3B131.4 (2)
C2A—N1A—Fe125.51 (13)C6B—C5B—N2B108.64 (19)
C4A—N2A—C6A106.42 (17)C6B—C5B—H5BA125.7
C4A—N2A—Fe112.58 (14)N2B—C5B—H5BA125.7
C6A—N2A—Fe140.88 (15)N3B—C6B—C5B107.06 (19)
C4A—N3A—C5A107.23 (18)N3B—C6B—H6BA126.5
C4A—N3A—H3AB126.4C5B—C6B—H6BA126.5
C5A—N3A—H3AB126.4C2C—C1C—N120.22 (17)
C3B—N1B—C2B118.14 (17)C2C—C1C—H1CA107.3
C3B—N1B—Fe115.93 (14)N—C1C—H1CA107.3
C2B—N1B—Fe125.72 (13)C2C—C1C—H1CB107.3
C4B—N2B—C5B106.05 (17)N—C1C—H1CB107.3
C4B—N2B—Fe111.71 (13)H1CA—C1C—H1CB106.9
C5B—N2B—Fe142.13 (15)N1C—C2C—C1C115.48 (17)
C4B—N3B—C6B107.04 (19)N1C—C2C—H2CA108.4
C4B—N3B—H3BB126.5C1C—C2C—H2CA108.4
C6B—N3B—H3BB126.5N1C—C2C—H2CB108.4
C3C—N1C—C2C118.37 (17)C1C—C2C—H2CB108.4
C3C—N1C—Fe116.85 (14)H2CA—C2C—H2CB107.5
C2C—N1C—Fe124.70 (13)N1C—C3C—C4C112.98 (18)
C4C—N2C—C5C106.43 (17)N1C—C3C—H3CA123.5
C4C—N2C—Fe112.39 (14)C4C—C3C—H3CA123.5
C5C—N2C—Fe141.17 (15)N2C—C4C—N3C110.58 (19)
C4C—N3C—C6C107.37 (19)N2C—C4C—C3C116.60 (18)
C4C—N3C—H3CB126.3N3C—C4C—C3C132.8 (2)
C6C—N3C—H3CB126.3C6C—C5C—N2C108.9 (2)
N—C—H0A109.5C6C—C5C—H5CA125.5
N—C—H0B109.5N2C—C5C—H5CA125.5
H0A—C—H0B109.5C5C—C6C—N3C106.71 (19)
N—C—H0C109.5C5C—C6C—H6CA126.6
H0A—C—H0C109.5N3C—C6C—H6CA126.6
N1C—Fe—N1A—C3A98.03 (15)Fe—N1A—C3A—C4A4.9 (2)
N2A—Fe—N1A—C3A5.49 (15)C6A—N2A—C4A—N3A0.5 (2)
N1B—Fe—N1A—C3A167.75 (15)Fe—N2A—C4A—N3A176.30 (13)
N2B—Fe—N1A—C3A86.44 (15)C6A—N2A—C4A—C3A179.43 (18)
N2A—Fe—N1A—C2A179.28 (16)Fe—N2A—C4A—C3A3.7 (2)
N1B—Fe—N1A—C2A7.49 (16)C5A—N3A—C4A—N2A0.6 (2)
N2B—Fe—N1A—C2A88.79 (16)C5A—N3A—C4A—C3A179.4 (2)
N1C—Fe—N2A—C4A99.71 (14)N1A—C3A—C4A—N2A0.7 (3)
N1A—Fe—N2A—C4A4.80 (14)N1A—C3A—C4A—N3A179.3 (2)
N2C—Fe—N2A—C4A178.99 (14)C4A—N3A—C5A—C6A0.4 (2)
N2B—Fe—N2A—C4A86.10 (14)N3A—C5A—C6A—N2A0.0 (2)
N1C—Fe—N2A—C6A85.1 (2)C4A—N2A—C6A—C5A0.3 (2)
N1A—Fe—N2A—C6A180.0 (2)Fe—N2A—C6A—C5A175.06 (17)
N2C—Fe—N2A—C6A3.8 (2)C—N—C1B—C2B151.74 (19)
N2B—Fe—N2A—C6A89.1 (2)C1C—N—C1B—C2B39.1 (3)
N1C—Fe—N1B—C3B167.02 (15)C1A—N—C1B—C2B95.6 (2)
N1A—Fe—N1B—C3B97.27 (15)C3B—N1B—C2B—C1B99.6 (2)
N2C—Fe—N1B—C3B85.81 (15)Fe—N1B—C2B—C1B85.8 (2)
N2B—Fe—N1B—C3B6.79 (15)N—C1B—C2B—N1B72.2 (2)
N1C—Fe—N1B—C2B7.71 (16)C2B—N1B—C3B—C4B178.72 (17)
N1A—Fe—N1B—C2B88.00 (16)Fe—N1B—C3B—C4B6.1 (2)
N2C—Fe—N1B—C2B88.92 (16)C5B—N2B—C4B—N3B0.2 (2)
N2B—Fe—N1B—C2B178.48 (16)Fe—N2B—C4B—N3B177.05 (14)
N2A—Fe—N2B—C4B178.30 (14)C5B—N2B—C4B—C3B178.36 (18)
N1A—Fe—N2B—C4B100.57 (14)Fe—N2B—C4B—C3B4.4 (2)
N1B—Fe—N2B—C4B5.82 (14)C6B—N3B—C4B—N2B0.1 (2)
N2C—Fe—N2B—C4B85.11 (14)C6B—N3B—C4B—C3B178.4 (2)
N2A—Fe—N2B—C5B2.7 (2)N1B—C3B—C4B—N2B1.0 (3)
N1A—Fe—N2B—C5B83.8 (2)N1B—C3B—C4B—N3B177.2 (2)
N1B—Fe—N2B—C5B178.5 (2)C4B—N2B—C5B—C6B0.4 (2)
N2C—Fe—N2B—C5B90.5 (2)Fe—N2B—C5B—C6B175.37 (17)
N2A—Fe—N1C—C3C91.28 (16)C4B—N3B—C6B—C5B0.4 (3)
N1A—Fe—N1C—C3C172.62 (16)N2B—C5B—C6B—N3B0.5 (3)
N1B—Fe—N1C—C3C92.11 (16)C—N—C1C—C2C153.57 (18)
N2C—Fe—N1C—C3C1.33 (15)C1B—N—C1C—C2C94.3 (2)
N2A—Fe—N1C—C2C85.53 (16)C1A—N—C1C—C2C40.6 (2)
N1A—Fe—N1C—C2C4.18 (16)C3C—N1C—C2C—C1C93.2 (2)
N1B—Fe—N1C—C2C91.09 (16)Fe—N1C—C2C—C1C90.1 (2)
N2C—Fe—N1C—C2C178.13 (16)N—C1C—C2C—N1C72.7 (2)
N1C—Fe—N2C—C4C0.15 (14)C2C—N1C—C3C—C4C179.14 (18)
N2A—Fe—N2C—C4C92.75 (15)Fe—N1C—C3C—C4C2.1 (2)
N1B—Fe—N2C—C4C93.72 (15)C5C—N2C—C4C—N3C0.1 (2)
N2B—Fe—N2C—C4C175.00 (15)Fe—N2C—C4C—N3C179.40 (14)
N2A—Fe—N2C—C5C88.0 (2)C5C—N2C—C4C—C3C179.55 (18)
N1B—Fe—N2C—C5C85.6 (2)Fe—N2C—C4C—C3C0.9 (2)
N2B—Fe—N2C—C5C4.3 (2)C6C—N3C—C4C—N2C0.1 (3)
C—N—C1A—C2A150.83 (19)C6C—N3C—C4C—C3C179.7 (2)
C1C—N—C1A—C2A96.4 (2)N1C—C3C—C4C—N2C2.0 (3)
C1B—N—C1A—C2A38.8 (3)N1C—C3C—C4C—N3C178.4 (2)
C3A—N1A—C2A—C1A98.1 (2)C4C—N2C—C5C—C6C0.3 (2)
Fe—N1A—C2A—C1A86.8 (2)Fe—N2C—C5C—C6C178.98 (18)
N—C1A—C2A—N1A73.3 (2)N2C—C5C—C6C—N3C0.4 (3)
C2A—N1A—C3A—C4A179.54 (17)C4C—N3C—C6C—C5C0.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W2···O14i0.81 (2)2.29 (4)2.938 (3)138 (5)
O2W—H2W1···O14ii0.82 (2)2.26 (2)2.987 (3)148 (4)
O2W—H2W2···O22iii0.82 (2)2.07 (2)2.861 (3)160 (4)
N3A—H3AB···O2W0.881.912.730 (3)155
N3B—H3BB···O1W0.881.952.752 (3)152
N3C—H3CB···O140.882.052.907 (3)163
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x, y+1, z; (iii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Fe(C19H27N10)](ClO4)3·2H2O
Mr785.74
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)13.9630 (18), 11.7810 (15), 37.182 (5)
V3)6116.4 (14)
Z8
Radiation typeMo Kα
µ (mm1)0.84
Crystal size (mm)0.54 × 0.45 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.682, 0.904
No. of measured, independent and
observed [I > 2σ(I)] reflections
65065, 8324, 6601
Rint0.054
(sin θ/λ)max1)0.689
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.108, 1.04
No. of reflections8324
No. of parameters436
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.76, 0.62

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W2···O14i0.807 (19)2.29 (4)2.938 (3)138 (5)
O2W—H2W1···O14ii0.820 (17)2.26 (2)2.987 (3)148 (4)
O2W—H2W2···O22iii0.821 (18)2.07 (2)2.861 (3)160 (4)
N3A—H3AB···O2W0.881.912.730 (3)155
N3B—H3BB···O1W0.881.952.752 (3)152
N3C—H3CB···O140.882.052.907 (3)163
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x, y+1, z; (iii) x+1/2, y+1/2, z.
 

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