Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040391/gg2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040391/gg2037Isup2.hkl |
CCDC reference: 660147
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in solvent or counterion
- R factor = 0.060
- wR factor = 0.204
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact C6 .. O6B .. 2.87 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 40 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.63 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 176
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Al-Noaimi, Yap & Crutchley (2004); Barigelletti et al. (2000); Chamchoumis & Potvin (1999); Collin et al. (1991); Duboc et al. (2006); Schubert et al. (2006); Steiner (1997); Uma et al. (2005); Wang et al. (2007); Wilkinson et al. (2004); Yucesan et al. (2005); Yutaka et al. (2005).
4'-(4-Methylphenyl)-2,2':6',2"-terpyridine (ttp) was prepared by an improved Kröhnke condensation method (Wang et al., 2007; Collin et al., 1991). A mixture of Mn(ClO4)2.6H2O (1 mmol), ttp (2 mmol) and H2O/MeOH (10 ml; 1:1) was placed in a 25 ml of Teflon-lined stainless steel vessel and heated under autogenous pressure at 432 K for 4 days, followed by cooling to room temperature at a rate of 5 K/h. Yellow block crystals of the title complex (I) were obtained in a yield of 38% based on Mn.
Each of the two [ClO4]- moieties was disordered and they were split into two sets of positions, with occupancy ratios of 0.505:0.495 and 0.738:0.262. The intra Cl—O and O—O distances were restrained to be 1.44 (1) and 2.35 (2) Å, respectively. Carbon-bound H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93 to 0.97 Å, with Uiso(H) = 1.2 or 1.5 Ueq(C).
Terpyridines are a family of widely used ligands (Schubert et al. 2006). Whereas a large number of metal derivatives of terpyridine and its substituted derivatives have been reported, there are few examples of metal derivatives of 4'-(4-methylphenyl)-2,2':6',2"-terpyridine ligand (denoted as ttp), and examples of crystal structure reports are limited to those of ruthenium (Chamchoumis & Potvin, 1999; Barigelletti et al., 2000; Al-Noaimi et al., 2004), copper (Uma et al., 2005; Yucesan et al., 2005), iridium (Yutaka et al., 2005; Wilkinson et al., 2004) and manganese (Duboc et al., 2006). The complex of Duboc et al. is [Mn(ttp)Cl2], in which Mn(II) is penta-coordinated. Here we report the title structure (I) from a hydrothermal reaction of manganese perchlorate and ttp.
As illustrated in Fig. 1, the Mn(II) centre is coordinated by six N atoms from two ttp ligands, and displays a distorted octahedral geometry. The tri-coordinating mode of the ttp ligands restricts the three pyridyl rings of each ttp and the central Mn(II) ion are very close to be coplanar. Such two planes are almost perpendicular with a dihedral angle of 89.1 (5)°. The two tolyl groups are twisted out of their connected terpyridyl moieties by 35.62 (4)° and 20.23 (6)°, respectively. Both perchlorate anions are disordered and were refined with two sets of disordered O atom positions for each. There are several C—H···O hydrogen bonds (Steiner, 1997) between the ttp ligand and the neighbouring perchloartes which involve the cations and counter-anions (Table 1).
For related literature, see: Al-Noaimi, Yap & Crutchley (2004); Barigelletti et al. (2000); Chamchoumis & Potvin (1999); Collin et al. (1991); Duboc et al. (2006); Schubert et al. (2006); Steiner (1997); Uma et al. (2005); Wang et al. (2007); Wilkinson et al. (2004); Yucesan et al. (2005); Yutaka et al. (2005).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
[Mn(C22H17N3)2](ClO4)2 | F(000) = 1852 |
Mr = 900.61 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8356 reflections |
a = 18.2372 (4) Å | θ = 1.4–28.0° |
b = 15.4778 (4) Å | µ = 0.50 mm−1 |
c = 15.9465 (4) Å | T = 293 K |
β = 110.339 (2)° | Block, yellow |
V = 4220.60 (18) Å3 | 0.25 × 0.19 × 0.16 mm |
Z = 4 |
Bruker APEXII area-detector diffractometer | 8296 independent reflections |
Radiation source: fine-focus sealed tube | 4836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
φ and ω scans | θmax = 26.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→22 |
Tmin = 0.885, Tmax = 0.924 | k = −17→19 |
45630 measured reflections | l = −19→19 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.1047P)2] where P = (Fo2 + 2Fc2)/3 |
8296 reflections | (Δ/σ)max = 0.002 |
644 parameters | Δρmax = 0.44 e Å−3 |
176 restraints | Δρmin = −0.46 e Å−3 |
[Mn(C22H17N3)2](ClO4)2 | V = 4220.60 (18) Å3 |
Mr = 900.61 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.2372 (4) Å | µ = 0.50 mm−1 |
b = 15.4778 (4) Å | T = 293 K |
c = 15.9465 (4) Å | 0.25 × 0.19 × 0.16 mm |
β = 110.339 (2)° |
Bruker APEXII area-detector diffractometer | 8296 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4836 reflections with I > 2σ(I) |
Tmin = 0.885, Tmax = 0.924 | Rint = 0.090 |
45630 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 176 restraints |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.44 e Å−3 |
8296 reflections | Δρmin = −0.46 e Å−3 |
644 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7202 (3) | 0.6693 (3) | 0.4596 (3) | 0.0771 (15) | |
H1 | 0.7742 | 0.6747 | 0.4759 | 0.092* | |
C2 | 0.6874 (4) | 0.6750 (4) | 0.5240 (4) | 0.0880 (17) | |
H2 | 0.7185 | 0.6837 | 0.5835 | 0.106* | |
C3 | 0.6072 (4) | 0.6677 (4) | 0.4998 (4) | 0.0935 (18) | |
H3 | 0.5835 | 0.6707 | 0.5428 | 0.112* | |
C4 | 0.5628 (3) | 0.6559 (4) | 0.4110 (4) | 0.0846 (17) | |
H4 | 0.5087 | 0.6517 | 0.3935 | 0.102* | |
C5 | 0.5989 (3) | 0.6504 (3) | 0.3479 (3) | 0.0557 (12) | |
C6 | 0.5569 (3) | 0.6388 (3) | 0.2515 (3) | 0.0545 (11) | |
C7 | 0.4766 (3) | 0.6394 (3) | 0.2116 (3) | 0.0626 (13) | |
H7 | 0.4456 | 0.6481 | 0.2465 | 0.075* | |
C8 | 0.4413 (3) | 0.6272 (3) | 0.1198 (3) | 0.0644 (13) | |
C9 | 0.4919 (3) | 0.6151 (3) | 0.0721 (3) | 0.0632 (13) | |
H9 | 0.4712 | 0.6055 | 0.0108 | 0.076* | |
C10 | 0.5717 (3) | 0.6171 (3) | 0.1141 (3) | 0.0550 (12) | |
C11 | 0.6290 (3) | 0.6082 (3) | 0.0682 (3) | 0.0583 (12) | |
C12 | 0.6073 (3) | 0.5995 (3) | −0.0238 (3) | 0.0698 (14) | |
H12 | 0.5548 | 0.5968 | −0.0596 | 0.084* | |
C13 | 0.6650 (4) | 0.5951 (4) | −0.0612 (3) | 0.0809 (16) | |
H13 | 0.6516 | 0.5887 | −0.1227 | 0.097* | |
C14 | 0.7417 (3) | 0.6002 (4) | −0.0077 (4) | 0.0814 (16) | |
H14 | 0.7812 | 0.5977 | −0.0319 | 0.098* | |
C15 | 0.7593 (3) | 0.6092 (3) | 0.0832 (3) | 0.0757 (15) | |
H15 | 0.8116 | 0.6133 | 0.1195 | 0.091* | |
C16 | 0.3552 (3) | 0.6262 (3) | 0.0749 (4) | 0.0742 (15) | |
C17 | 0.3057 (3) | 0.6089 (3) | 0.1227 (4) | 0.0838 (17) | |
H17 | 0.3266 | 0.6005 | 0.1842 | 0.101* | |
C18 | 0.2248 (3) | 0.6042 (4) | 0.0786 (5) | 0.096 (2) | |
H18 | 0.1924 | 0.5940 | 0.1115 | 0.115* | |
C19 | 0.1920 (4) | 0.6145 (4) | −0.0137 (6) | 0.105 (2) | |
C20 | 0.2407 (4) | 0.6317 (5) | −0.0603 (5) | 0.125 (3) | |
H20 | 0.2196 | 0.6388 | −0.1220 | 0.150* | |
C21 | 0.3212 (4) | 0.6388 (4) | −0.0173 (5) | 0.112 (2) | |
H21 | 0.3528 | 0.6522 | −0.0504 | 0.134* | |
C22 | 0.1048 (4) | 0.6031 (6) | −0.0606 (6) | 0.164 (4) | |
H22A | 0.0907 | 0.5443 | −0.0545 | 0.247* | |
H22B | 0.0913 | 0.6168 | −0.1229 | 0.247* | |
H22C | 0.0772 | 0.6410 | −0.0342 | 0.247* | |
C23 | 0.7323 (3) | 0.8362 (4) | 0.2579 (3) | 0.0607 (12) | |
H23 | 0.6790 | 0.8301 | 0.2466 | 0.073* | |
C24 | 0.7615 (3) | 0.9169 (4) | 0.2579 (3) | 0.0695 (14) | |
H24 | 0.7287 | 0.9647 | 0.2473 | 0.083* | |
C25 | 0.8405 (3) | 0.9271 (4) | 0.2737 (4) | 0.0836 (16) | |
H25 | 0.8618 | 0.9815 | 0.2730 | 0.100* | |
C26 | 0.8870 (3) | 0.8537 (4) | 0.2909 (4) | 0.0765 (15) | |
H26 | 0.9405 | 0.8585 | 0.3024 | 0.092* | |
C27 | 0.8542 (3) | 0.7738 (3) | 0.2908 (3) | 0.0526 (11) | |
C28 | 0.8998 (3) | 0.6925 (3) | 0.3100 (3) | 0.0511 (11) | |
C29 | 0.9783 (3) | 0.6870 (3) | 0.3250 (3) | 0.0569 (12) | |
H29 | 1.0057 | 0.7368 | 0.3214 | 0.068* | |
C30 | 1.0176 (3) | 0.6093 (3) | 0.3452 (3) | 0.0576 (12) | |
C31 | 0.9733 (3) | 0.5368 (3) | 0.3503 (3) | 0.0643 (13) | |
H31 | 0.9970 | 0.4829 | 0.3646 | 0.077* | |
C32 | 0.8946 (3) | 0.5458 (3) | 0.3341 (3) | 0.0582 (12) | |
C33 | 0.8412 (3) | 0.4725 (3) | 0.3363 (3) | 0.0661 (13) | |
C34 | 0.8671 (4) | 0.3912 (4) | 0.3655 (5) | 0.097 (2) | |
H34 | 0.9202 | 0.3784 | 0.3847 | 0.117* | |
C35 | 0.8139 (4) | 0.3288 (4) | 0.3663 (5) | 0.113 (2) | |
H35 | 0.8307 | 0.2731 | 0.3853 | 0.135* | |
C36 | 0.7364 (4) | 0.3486 (4) | 0.3390 (5) | 0.105 (2) | |
H36 | 0.6997 | 0.3072 | 0.3397 | 0.126* | |
C37 | 0.7140 (3) | 0.4313 (4) | 0.3104 (4) | 0.0926 (18) | |
H37 | 0.6611 | 0.4449 | 0.2911 | 0.111* | |
C38 | 1.1023 (3) | 0.6038 (3) | 0.3604 (3) | 0.0613 (13) | |
C39 | 1.1345 (3) | 0.6565 (3) | 0.3126 (3) | 0.0739 (15) | |
H39 | 1.1023 | 0.6930 | 0.2689 | 0.089* | |
C40 | 1.2146 (3) | 0.6558 (4) | 0.3292 (4) | 0.0788 (15) | |
H40 | 1.2348 | 0.6917 | 0.2959 | 0.095* | |
C41 | 1.2643 (3) | 0.6038 (4) | 0.3929 (4) | 0.0776 (15) | |
C42 | 1.2313 (3) | 0.5503 (4) | 0.4403 (4) | 0.0874 (18) | |
H42 | 1.2636 | 0.5144 | 0.4846 | 0.105* | |
C43 | 1.1523 (3) | 0.5490 (4) | 0.4233 (3) | 0.0802 (16) | |
H43 | 1.1318 | 0.5107 | 0.4544 | 0.096* | |
C44 | 1.3513 (3) | 0.6065 (4) | 0.4123 (4) | 0.108 (2) | |
H44A | 1.3619 | 0.6388 | 0.3664 | 0.162* | |
H44B | 1.3708 | 0.5486 | 0.4137 | 0.162* | |
H44C | 1.3767 | 0.6336 | 0.4692 | 0.162* | |
Mn1 | 0.73059 (4) | 0.63041 (5) | 0.26895 (4) | 0.0557 (3) | |
N1 | 0.6769 (2) | 0.6561 (2) | 0.3723 (2) | 0.0605 (10) | |
N2 | 0.6036 (2) | 0.6273 (2) | 0.2033 (2) | 0.0541 (9) | |
N3 | 0.7050 (2) | 0.6124 (2) | 0.1215 (2) | 0.0605 (10) | |
N4 | 0.7769 (2) | 0.7645 (2) | 0.2734 (2) | 0.0548 (9) | |
N5 | 0.8585 (2) | 0.6222 (2) | 0.3133 (2) | 0.0542 (9) | |
N6 | 0.7649 (2) | 0.4934 (3) | 0.3088 (3) | 0.0692 (11) | |
Cl1A | 0.9435 (4) | 0.7412 (4) | 0.5646 (5) | 0.103 (2) | 0.505 (7) |
Cl2A | 0.50345 (19) | 0.9028 (2) | 0.1940 (2) | 0.0725 (12) | 0.739 (9) |
O1A | 0.8876 (6) | 0.7478 (8) | 0.6104 (6) | 0.155 (4) | 0.505 (7) |
O2A | 1.0179 (6) | 0.7748 (10) | 0.6119 (10) | 0.200 (7) | 0.505 (7) |
O3A | 0.9374 (5) | 0.6574 (5) | 0.5272 (6) | 0.119 (4) | 0.505 (7) |
O4A | 0.9015 (7) | 0.8002 (7) | 0.4925 (7) | 0.164 (5) | 0.505 (7) |
O5A | 0.5726 (3) | 0.9584 (4) | 0.2206 (5) | 0.106 (2) | 0.739 (9) |
O6A | 0.5221 (5) | 0.8284 (4) | 0.1549 (6) | 0.131 (3) | 0.739 (9) |
O7A | 0.4830 (5) | 0.8790 (7) | 0.2698 (5) | 0.134 (3) | 0.739 (9) |
O8A | 0.4411 (3) | 0.9499 (5) | 0.1343 (4) | 0.121 (3) | 0.739 (9) |
Cl1B | 0.9560 (5) | 0.7580 (7) | 0.5794 (7) | 0.164 (4) | 0.495 (7) |
Cl2B | 0.5018 (10) | 0.8960 (11) | 0.2035 (11) | 0.167 (7) | 0.261 (9) |
O1B | 0.9831 (7) | 0.7036 (7) | 0.6559 (6) | 0.146 (4) | 0.495 (7) |
O2B | 1.0134 (6) | 0.7686 (8) | 0.5385 (8) | 0.151 (5) | 0.495 (7) |
O3B | 0.8915 (9) | 0.7227 (15) | 0.5115 (11) | 0.291 (9) | 0.495 (7) |
O4B | 0.9392 (9) | 0.8412 (9) | 0.6074 (10) | 0.228 (6) | 0.495 (7) |
O5B | 0.5485 (16) | 0.9575 (18) | 0.1749 (18) | 0.197 (10) | 0.261 (9) |
O6B | 0.5510 (11) | 0.8237 (12) | 0.2409 (19) | 0.168 (9) | 0.261 (9) |
O7B | 0.4791 (13) | 0.9387 (15) | 0.2706 (14) | 0.139 (8) | 0.261 (9) |
O8B | 0.4373 (11) | 0.867 (2) | 0.1298 (13) | 0.176 (9) | 0.261 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.087 (4) | 0.077 (4) | 0.063 (3) | 0.000 (3) | 0.021 (3) | 0.004 (3) |
C2 | 0.120 (5) | 0.088 (4) | 0.061 (3) | −0.009 (4) | 0.037 (4) | 0.001 (3) |
C3 | 0.129 (6) | 0.091 (5) | 0.085 (4) | −0.001 (4) | 0.069 (4) | 0.002 (3) |
C4 | 0.088 (4) | 0.099 (5) | 0.077 (4) | −0.006 (3) | 0.041 (3) | −0.010 (3) |
C5 | 0.062 (3) | 0.053 (3) | 0.060 (3) | −0.006 (2) | 0.031 (2) | −0.001 (2) |
C6 | 0.056 (3) | 0.049 (3) | 0.062 (3) | −0.001 (2) | 0.026 (2) | 0.000 (2) |
C7 | 0.056 (3) | 0.059 (3) | 0.082 (3) | −0.005 (2) | 0.036 (3) | 0.003 (3) |
C8 | 0.065 (3) | 0.045 (3) | 0.082 (3) | −0.004 (2) | 0.023 (3) | 0.004 (2) |
C9 | 0.066 (3) | 0.058 (3) | 0.062 (3) | −0.009 (2) | 0.019 (2) | −0.005 (2) |
C10 | 0.060 (3) | 0.050 (3) | 0.056 (3) | −0.012 (2) | 0.021 (2) | −0.006 (2) |
C11 | 0.070 (3) | 0.055 (3) | 0.057 (3) | −0.014 (2) | 0.031 (2) | −0.005 (2) |
C12 | 0.076 (3) | 0.071 (4) | 0.068 (3) | −0.021 (3) | 0.032 (3) | −0.013 (3) |
C13 | 0.108 (5) | 0.082 (4) | 0.066 (3) | −0.021 (3) | 0.046 (3) | −0.017 (3) |
C14 | 0.095 (4) | 0.083 (4) | 0.085 (4) | −0.019 (3) | 0.056 (3) | −0.022 (3) |
C15 | 0.073 (3) | 0.092 (4) | 0.073 (3) | −0.010 (3) | 0.039 (3) | −0.015 (3) |
C16 | 0.059 (3) | 0.057 (3) | 0.096 (4) | −0.004 (3) | 0.014 (3) | 0.011 (3) |
C17 | 0.059 (3) | 0.080 (4) | 0.115 (4) | −0.001 (3) | 0.034 (3) | −0.006 (3) |
C18 | 0.059 (4) | 0.074 (4) | 0.155 (6) | 0.002 (3) | 0.038 (4) | −0.012 (4) |
C19 | 0.061 (4) | 0.084 (5) | 0.147 (6) | 0.005 (3) | 0.009 (4) | 0.013 (4) |
C20 | 0.076 (5) | 0.131 (7) | 0.136 (6) | −0.001 (4) | −0.004 (4) | 0.050 (5) |
C21 | 0.073 (4) | 0.121 (6) | 0.126 (5) | −0.006 (4) | 0.015 (4) | 0.047 (4) |
C22 | 0.065 (4) | 0.175 (9) | 0.206 (9) | 0.011 (5) | −0.014 (5) | 0.010 (7) |
C23 | 0.066 (3) | 0.062 (4) | 0.063 (3) | 0.010 (3) | 0.034 (2) | 0.003 (2) |
C24 | 0.074 (4) | 0.061 (4) | 0.082 (3) | 0.019 (3) | 0.038 (3) | 0.011 (3) |
C25 | 0.089 (4) | 0.049 (4) | 0.126 (5) | 0.004 (3) | 0.054 (4) | 0.007 (3) |
C26 | 0.055 (3) | 0.062 (4) | 0.116 (4) | 0.002 (3) | 0.034 (3) | 0.007 (3) |
C27 | 0.053 (3) | 0.053 (3) | 0.056 (3) | −0.001 (2) | 0.025 (2) | −0.001 (2) |
C28 | 0.054 (3) | 0.050 (3) | 0.051 (2) | 0.001 (2) | 0.021 (2) | −0.001 (2) |
C29 | 0.054 (3) | 0.053 (3) | 0.066 (3) | −0.002 (2) | 0.024 (2) | 0.003 (2) |
C30 | 0.059 (3) | 0.057 (3) | 0.059 (3) | 0.003 (2) | 0.022 (2) | −0.001 (2) |
C31 | 0.060 (3) | 0.055 (3) | 0.080 (3) | 0.011 (3) | 0.026 (2) | 0.003 (3) |
C32 | 0.060 (3) | 0.053 (3) | 0.065 (3) | 0.002 (2) | 0.025 (2) | 0.000 (2) |
C33 | 0.059 (3) | 0.058 (4) | 0.084 (3) | 0.000 (3) | 0.030 (3) | 0.001 (3) |
C34 | 0.083 (4) | 0.054 (4) | 0.160 (6) | 0.010 (3) | 0.050 (4) | 0.015 (4) |
C35 | 0.111 (6) | 0.059 (4) | 0.175 (7) | −0.007 (4) | 0.059 (5) | 0.019 (4) |
C36 | 0.088 (5) | 0.069 (5) | 0.167 (6) | −0.015 (4) | 0.058 (4) | 0.009 (4) |
C37 | 0.072 (4) | 0.067 (4) | 0.147 (5) | −0.011 (3) | 0.049 (4) | 0.010 (4) |
C38 | 0.054 (3) | 0.064 (3) | 0.069 (3) | 0.003 (2) | 0.025 (2) | −0.003 (3) |
C39 | 0.057 (3) | 0.079 (4) | 0.089 (4) | 0.007 (3) | 0.029 (3) | 0.014 (3) |
C40 | 0.062 (3) | 0.087 (4) | 0.089 (4) | 0.000 (3) | 0.029 (3) | 0.007 (3) |
C41 | 0.054 (3) | 0.090 (4) | 0.089 (4) | 0.000 (3) | 0.026 (3) | −0.010 (3) |
C42 | 0.065 (4) | 0.107 (5) | 0.082 (4) | 0.026 (3) | 0.015 (3) | 0.012 (3) |
C43 | 0.068 (4) | 0.092 (4) | 0.081 (3) | 0.016 (3) | 0.028 (3) | 0.016 (3) |
C44 | 0.057 (4) | 0.144 (6) | 0.125 (5) | 0.005 (4) | 0.033 (3) | −0.009 (4) |
Mn1 | 0.0487 (4) | 0.0608 (5) | 0.0601 (4) | −0.0020 (3) | 0.0222 (3) | −0.0027 (3) |
N1 | 0.067 (3) | 0.061 (3) | 0.057 (2) | −0.003 (2) | 0.025 (2) | 0.0038 (19) |
N2 | 0.059 (2) | 0.054 (2) | 0.054 (2) | −0.0068 (18) | 0.0249 (18) | −0.0054 (17) |
N3 | 0.059 (2) | 0.067 (3) | 0.060 (2) | −0.010 (2) | 0.027 (2) | −0.0097 (19) |
N4 | 0.053 (2) | 0.059 (3) | 0.058 (2) | 0.0064 (19) | 0.0251 (17) | −0.0008 (18) |
N5 | 0.059 (2) | 0.046 (3) | 0.061 (2) | −0.001 (2) | 0.0239 (18) | −0.0036 (18) |
N6 | 0.063 (3) | 0.056 (3) | 0.095 (3) | −0.007 (2) | 0.037 (2) | 0.003 (2) |
Cl1A | 0.064 (3) | 0.143 (4) | 0.086 (3) | 0.013 (3) | 0.006 (2) | −0.028 (3) |
Cl2A | 0.065 (2) | 0.077 (2) | 0.0813 (19) | 0.0177 (15) | 0.0326 (15) | 0.0062 (14) |
O1A | 0.154 (8) | 0.206 (11) | 0.118 (7) | 0.024 (8) | 0.065 (6) | −0.052 (7) |
O2A | 0.100 (7) | 0.234 (13) | 0.211 (13) | −0.002 (8) | −0.017 (7) | −0.091 (11) |
O3A | 0.098 (6) | 0.144 (7) | 0.096 (6) | 0.034 (5) | 0.008 (5) | −0.042 (5) |
O4A | 0.158 (9) | 0.174 (9) | 0.138 (8) | 0.041 (8) | 0.025 (6) | 0.035 (7) |
O5A | 0.082 (4) | 0.100 (5) | 0.127 (5) | −0.011 (3) | 0.024 (3) | −0.002 (4) |
O6A | 0.168 (7) | 0.068 (4) | 0.194 (7) | 0.002 (4) | 0.111 (6) | −0.016 (4) |
O7A | 0.110 (5) | 0.213 (10) | 0.094 (4) | 0.014 (6) | 0.056 (4) | 0.030 (5) |
O8A | 0.094 (4) | 0.132 (6) | 0.115 (4) | 0.031 (4) | 0.010 (3) | 0.026 (4) |
Cl1B | 0.086 (5) | 0.301 (10) | 0.098 (4) | 0.035 (5) | 0.024 (4) | −0.063 (5) |
Cl2B | 0.116 (12) | 0.184 (15) | 0.182 (14) | 0.005 (9) | 0.029 (9) | −0.003 (11) |
O1B | 0.160 (9) | 0.198 (10) | 0.123 (7) | −0.022 (7) | 0.104 (6) | −0.049 (6) |
O2B | 0.128 (8) | 0.193 (11) | 0.157 (9) | 0.048 (7) | 0.079 (7) | 0.047 (8) |
O3B | 0.176 (11) | 0.421 (19) | 0.226 (13) | −0.096 (14) | 0.006 (10) | −0.041 (13) |
O4B | 0.201 (12) | 0.299 (13) | 0.179 (11) | 0.104 (11) | 0.060 (9) | −0.021 (9) |
O5B | 0.177 (19) | 0.208 (19) | 0.20 (2) | −0.025 (15) | 0.061 (14) | 0.009 (16) |
O6B | 0.111 (13) | 0.149 (15) | 0.215 (19) | 0.007 (10) | 0.020 (12) | −0.020 (13) |
O7B | 0.105 (13) | 0.121 (16) | 0.167 (15) | −0.005 (11) | 0.018 (10) | −0.009 (12) |
O8B | 0.126 (14) | 0.22 (2) | 0.152 (15) | 0.008 (13) | 0.017 (11) | −0.020 (14) |
C1—N1 | 1.357 (6) | C28—N5 | 1.334 (5) |
C1—C2 | 1.359 (7) | C28—C29 | 1.370 (6) |
C1—H1 | 0.9300 | C29—C30 | 1.380 (6) |
C2—C3 | 1.382 (7) | C29—H29 | 0.9300 |
C2—H2 | 0.9300 | C30—C31 | 1.403 (6) |
C3—C4 | 1.377 (7) | C30—C38 | 1.480 (6) |
C3—H3 | 0.9300 | C31—C32 | 1.373 (6) |
C4—C5 | 1.383 (7) | C31—H31 | 0.9300 |
C4—H4 | 0.9300 | C32—N5 | 1.339 (5) |
C5—N1 | 1.341 (5) | C32—C33 | 1.503 (6) |
C5—C6 | 1.472 (6) | C33—N6 | 1.346 (6) |
C6—N2 | 1.343 (5) | C33—C34 | 1.368 (7) |
C6—C7 | 1.379 (6) | C34—C35 | 1.373 (8) |
C7—C8 | 1.392 (7) | C34—H34 | 0.9300 |
C7—H7 | 0.9300 | C35—C36 | 1.360 (8) |
C8—C9 | 1.398 (7) | C35—H35 | 0.9300 |
C8—C16 | 1.481 (7) | C36—C37 | 1.372 (8) |
C9—C10 | 1.374 (6) | C36—H36 | 0.9300 |
C9—H9 | 0.9300 | C37—N6 | 1.342 (6) |
C10—N2 | 1.346 (5) | C37—H37 | 0.9300 |
C10—C11 | 1.476 (6) | C38—C39 | 1.379 (7) |
C11—N3 | 1.352 (6) | C38—C43 | 1.386 (6) |
C11—C12 | 1.386 (6) | C39—C40 | 1.391 (6) |
C12—C13 | 1.380 (7) | C39—H39 | 0.9300 |
C12—H12 | 0.9300 | C40—C41 | 1.364 (7) |
C13—C14 | 1.365 (7) | C40—H40 | 0.9300 |
C13—H13 | 0.9300 | C41—C42 | 1.391 (8) |
C14—C15 | 1.377 (7) | C41—C44 | 1.508 (7) |
C14—H14 | 0.9300 | C42—C43 | 1.371 (7) |
C15—N3 | 1.333 (6) | C42—H42 | 0.9300 |
C15—H15 | 0.9300 | C43—H43 | 0.9300 |
C16—C17 | 1.395 (7) | C44—H44A | 0.9600 |
C16—C21 | 1.397 (8) | C44—H44B | 0.9600 |
C17—C18 | 1.397 (7) | C44—H44C | 0.9600 |
C17—H17 | 0.9300 | Mn1—N2 | 2.185 (4) |
C18—C19 | 1.392 (9) | Mn1—N5 | 2.193 (4) |
C18—H18 | 0.9300 | Mn1—N1 | 2.225 (4) |
C19—C20 | 1.368 (10) | Mn1—N4 | 2.233 (4) |
C19—C22 | 1.514 (8) | Mn1—N6 | 2.240 (4) |
C20—C21 | 1.392 (8) | Mn1—N3 | 2.250 (4) |
C20—H20 | 0.9300 | Cl1A—O2A | 1.404 (8) |
C21—H21 | 0.9300 | Cl1A—O3A | 1.416 (8) |
C22—H22A | 0.9600 | Cl1A—O1A | 1.448 (8) |
C22—H22B | 0.9600 | Cl1A—O4A | 1.459 (8) |
C22—H22C | 0.9600 | Cl2A—O6A | 1.406 (6) |
C23—N4 | 1.347 (6) | Cl2A—O8A | 1.407 (5) |
C23—C24 | 1.358 (7) | Cl2A—O7A | 1.431 (6) |
C23—H23 | 0.9300 | Cl2A—O5A | 1.462 (5) |
C24—C25 | 1.382 (7) | Cl1B—O3B | 1.403 (9) |
C24—H24 | 0.9300 | Cl1B—O1B | 1.422 (9) |
C25—C26 | 1.388 (7) | Cl1B—O2B | 1.423 (9) |
C25—H25 | 0.9300 | Cl1B—O4B | 1.430 (9) |
C26—C27 | 1.373 (6) | Cl2B—O8B | 1.416 (10) |
C26—H26 | 0.9300 | Cl2B—O6B | 1.430 (10) |
C27—N4 | 1.347 (5) | Cl2B—O7B | 1.435 (10) |
C27—C28 | 1.481 (6) | Cl2B—O5B | 1.452 (10) |
N1—C1—C2 | 122.2 (5) | C31—C32—C33 | 124.2 (4) |
N1—C1—H1 | 118.9 | N6—C33—C34 | 121.8 (5) |
C2—C1—H1 | 118.9 | N6—C33—C32 | 114.7 (4) |
C1—C2—C3 | 119.0 (5) | C34—C33—C32 | 123.5 (5) |
C1—C2—H2 | 120.5 | C33—C34—C35 | 119.3 (6) |
C3—C2—H2 | 120.5 | C33—C34—H34 | 120.3 |
C4—C3—C2 | 119.0 (5) | C35—C34—H34 | 120.3 |
C4—C3—H3 | 120.5 | C36—C35—C34 | 119.8 (6) |
C2—C3—H3 | 120.5 | C36—C35—H35 | 120.1 |
C3—C4—C5 | 119.9 (5) | C34—C35—H35 | 120.1 |
C3—C4—H4 | 120.1 | C35—C36—C37 | 118.2 (6) |
C5—C4—H4 | 120.1 | C35—C36—H36 | 120.9 |
N1—C5—C4 | 120.7 (4) | C37—C36—H36 | 120.9 |
N1—C5—C6 | 115.2 (4) | N6—C37—C36 | 123.1 (5) |
C4—C5—C6 | 124.1 (5) | N6—C37—H37 | 118.4 |
N2—C6—C7 | 121.3 (4) | C36—C37—H37 | 118.4 |
N2—C6—C5 | 114.2 (4) | C39—C38—C43 | 117.6 (5) |
C7—C6—C5 | 124.4 (4) | C39—C38—C30 | 119.7 (4) |
C6—C7—C8 | 120.9 (5) | C43—C38—C30 | 122.7 (5) |
C6—C7—H7 | 119.5 | C38—C39—C40 | 120.7 (5) |
C8—C7—H7 | 119.5 | C38—C39—H39 | 119.6 |
C7—C8—C9 | 116.0 (4) | C40—C39—H39 | 119.6 |
C7—C8—C16 | 122.3 (5) | C41—C40—C39 | 121.9 (5) |
C9—C8—C16 | 121.7 (5) | C41—C40—H40 | 119.0 |
C10—C9—C8 | 121.3 (4) | C39—C40—H40 | 119.0 |
C10—C9—H9 | 119.3 | C40—C41—C42 | 117.0 (5) |
C8—C9—H9 | 119.3 | C40—C41—C44 | 121.1 (6) |
N2—C10—C9 | 120.8 (4) | C42—C41—C44 | 121.9 (5) |
N2—C10—C11 | 114.5 (4) | C43—C42—C41 | 121.6 (5) |
C9—C10—C11 | 124.7 (4) | C43—C42—H42 | 119.2 |
N3—C11—C12 | 121.6 (4) | C41—C42—H42 | 119.2 |
N3—C11—C10 | 115.6 (4) | C42—C43—C38 | 121.1 (5) |
C12—C11—C10 | 122.8 (4) | C42—C43—H43 | 119.5 |
C13—C12—C11 | 118.8 (5) | C38—C43—H43 | 119.5 |
C13—C12—H12 | 120.6 | N2—Mn1—N5 | 169.82 (13) |
C11—C12—H12 | 120.6 | N2—Mn1—N1 | 72.13 (13) |
C14—C13—C12 | 119.7 (5) | N5—Mn1—N1 | 117.65 (13) |
C14—C13—H13 | 120.1 | N2—Mn1—N4 | 111.21 (13) |
C12—C13—H13 | 120.1 | N5—Mn1—N4 | 72.26 (14) |
C13—C14—C15 | 118.5 (5) | N1—Mn1—N4 | 94.00 (13) |
C13—C14—H14 | 120.7 | N2—Mn1—N6 | 105.07 (14) |
C15—C14—H14 | 120.7 | N5—Mn1—N6 | 72.12 (14) |
N3—C15—C14 | 123.2 (5) | N1—Mn1—N6 | 96.33 (14) |
N3—C15—H15 | 118.4 | N4—Mn1—N6 | 143.71 (14) |
C14—C15—H15 | 118.4 | N2—Mn1—N3 | 72.32 (14) |
C17—C16—C21 | 117.8 (5) | N5—Mn1—N3 | 98.07 (14) |
C17—C16—C8 | 121.1 (5) | N1—Mn1—N3 | 144.22 (14) |
C21—C16—C8 | 121.0 (6) | N4—Mn1—N3 | 94.98 (13) |
C16—C17—C18 | 120.4 (6) | N6—Mn1—N3 | 96.61 (14) |
C16—C17—H17 | 119.8 | C5—N1—C1 | 119.2 (4) |
C18—C17—H17 | 119.8 | C5—N1—Mn1 | 118.0 (3) |
C19—C18—C17 | 121.1 (6) | C1—N1—Mn1 | 122.5 (3) |
C19—C18—H18 | 119.5 | C6—N2—C10 | 119.5 (4) |
C17—C18—H18 | 119.5 | C6—N2—Mn1 | 120.0 (3) |
C20—C19—C18 | 118.4 (6) | C10—N2—Mn1 | 120.4 (3) |
C20—C19—C22 | 121.5 (7) | C15—N3—C11 | 118.1 (4) |
C18—C19—C22 | 120.1 (7) | C15—N3—Mn1 | 124.6 (3) |
C19—C20—C21 | 121.3 (7) | C11—N3—Mn1 | 117.3 (3) |
C19—C20—H20 | 119.3 | C27—N4—C23 | 118.2 (4) |
C21—C20—H20 | 119.3 | C27—N4—Mn1 | 117.6 (3) |
C20—C21—C16 | 120.9 (7) | C23—N4—Mn1 | 124.2 (3) |
C20—C21—H21 | 119.5 | C28—N5—C32 | 119.6 (4) |
C16—C21—H21 | 119.5 | C28—N5—Mn1 | 119.5 (3) |
N4—C23—C24 | 123.1 (5) | C32—N5—Mn1 | 120.5 (3) |
N4—C23—H23 | 118.5 | C37—N6—C33 | 117.7 (5) |
C24—C23—H23 | 118.5 | C37—N6—Mn1 | 123.9 (4) |
C23—C24—C25 | 119.3 (5) | C33—N6—Mn1 | 118.3 (3) |
C23—C24—H24 | 120.4 | O2A—Cl1A—O3A | 119.0 (8) |
C25—C24—H24 | 120.4 | O2A—Cl1A—O1A | 114.9 (9) |
C24—C25—C26 | 118.0 (5) | O3A—Cl1A—O1A | 108.1 (7) |
C24—C25—H25 | 121.0 | O2A—Cl1A—O4A | 109.7 (9) |
C26—C25—H25 | 121.0 | O3A—Cl1A—O4A | 107.5 (8) |
C27—C26—C25 | 120.0 (5) | O1A—Cl1A—O4A | 94.8 (7) |
C27—C26—H26 | 120.0 | O6A—Cl2A—O8A | 112.8 (5) |
C25—C26—H26 | 120.0 | O6A—Cl2A—O7A | 109.8 (5) |
N4—C27—C26 | 121.4 (4) | O8A—Cl2A—O7A | 108.6 (5) |
N4—C27—C28 | 115.0 (4) | O6A—Cl2A—O5A | 107.1 (4) |
C26—C27—C28 | 123.5 (4) | O8A—Cl2A—O5A | 107.7 (4) |
N5—C28—C29 | 120.9 (4) | O7A—Cl2A—O5A | 111.0 (5) |
N5—C28—C27 | 114.7 (4) | O3B—Cl1B—O1B | 112.3 (12) |
C29—C28—C27 | 124.4 (4) | O3B—Cl1B—O2B | 104.1 (10) |
C28—C29—C30 | 121.4 (4) | O1B—Cl1B—O2B | 111.7 (8) |
C28—C29—H29 | 119.3 | O3B—Cl1B—O4B | 112.2 (11) |
C30—C29—H29 | 119.3 | O1B—Cl1B—O4B | 108.3 (9) |
C29—C30—C31 | 116.6 (4) | O2B—Cl1B—O4B | 108.1 (10) |
C29—C30—C38 | 121.1 (4) | O8B—Cl2B—O6B | 108.5 (13) |
C31—C30—C38 | 122.3 (4) | O8B—Cl2B—O7B | 113.2 (13) |
C32—C31—C30 | 119.6 (4) | O6B—Cl2B—O7B | 110.5 (13) |
C32—C31—H31 | 120.2 | O8B—Cl2B—O5B | 110.9 (14) |
C30—C31—H31 | 120.2 | O6B—Cl2B—O5B | 106.9 (13) |
N5—C32—C31 | 121.9 (4) | O7B—Cl2B—O5B | 106.6 (13) |
N5—C32—C33 | 113.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3B | 0.93 | 2.15 | 3.055 (15) | 165 |
C3—H3···O6Ai | 0.93 | 2.42 | 3.347 (9) | 176 |
C13—H13···O5Aii | 0.93 | 2.52 | 3.400 (9) | 158 |
C15—H15···O4Bii | 0.93 | 2.50 | 3.260 (16) | 139 |
C22—H22C···O2Biii | 0.96 | 2.37 | 3.324 (14) | 177 |
C23—H23···O6B | 0.93 | 2.31 | 3.23 (2) | 171 |
C34—H34···O3Aiv | 0.93 | 2.55 | 3.458 (11) | 167 |
C34—H34···O1Biv | 0.93 | 2.44 | 3.223 (12) | 142 |
C37—H37···O8Av | 0.93 | 2.54 | 3.255 (9) | 134 |
C37—H37···O7Bv | 0.93 | 2.40 | 3.31 (2) | 164 |
C39—H39···O2Aii | 0.93 | 2.49 | 3.341 (12) | 152 |
C44—H44C···O8Bvi | 0.96 | 2.41 | 3.30 (2) | 153 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C22H17N3)2](ClO4)2 |
Mr | 900.61 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 18.2372 (4), 15.4778 (4), 15.9465 (4) |
β (°) | 110.339 (2) |
V (Å3) | 4220.60 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.25 × 0.19 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.885, 0.924 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45630, 8296, 4836 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.204, 0.98 |
No. of reflections | 8296 |
No. of parameters | 644 |
No. of restraints | 176 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.46 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3B | 0.93 | 2.15 | 3.055 (15) | 165 |
C3—H3···O6Ai | 0.93 | 2.42 | 3.347 (9) | 176 |
C13—H13···O5Aii | 0.93 | 2.52 | 3.400 (9) | 158 |
C15—H15···O4Bii | 0.93 | 2.50 | 3.260 (16) | 139 |
C22—H22C···O2Biii | 0.96 | 2.37 | 3.324 (14) | 177 |
C23—H23···O6B | 0.93 | 2.31 | 3.23 (2) | 171 |
C34—H34···O3Aiv | 0.93 | 2.55 | 3.458 (11) | 167 |
C34—H34···O1Biv | 0.93 | 2.44 | 3.223 (12) | 142 |
C37—H37···O8Av | 0.93 | 2.54 | 3.255 (9) | 134 |
C37—H37···O7Bv | 0.93 | 2.40 | 3.31 (2) | 164 |
C39—H39···O2Aii | 0.93 | 2.49 | 3.341 (12) | 152 |
C44—H44C···O8Bvi | 0.96 | 2.41 | 3.30 (2) | 153 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x+1, −y+3/2, z+1/2. |
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Terpyridines are a family of widely used ligands (Schubert et al. 2006). Whereas a large number of metal derivatives of terpyridine and its substituted derivatives have been reported, there are few examples of metal derivatives of 4'-(4-methylphenyl)-2,2':6',2"-terpyridine ligand (denoted as ttp), and examples of crystal structure reports are limited to those of ruthenium (Chamchoumis & Potvin, 1999; Barigelletti et al., 2000; Al-Noaimi et al., 2004), copper (Uma et al., 2005; Yucesan et al., 2005), iridium (Yutaka et al., 2005; Wilkinson et al., 2004) and manganese (Duboc et al., 2006). The complex of Duboc et al. is [Mn(ttp)Cl2], in which Mn(II) is penta-coordinated. Here we report the title structure (I) from a hydrothermal reaction of manganese perchlorate and ttp.
As illustrated in Fig. 1, the Mn(II) centre is coordinated by six N atoms from two ttp ligands, and displays a distorted octahedral geometry. The tri-coordinating mode of the ttp ligands restricts the three pyridyl rings of each ttp and the central Mn(II) ion are very close to be coplanar. Such two planes are almost perpendicular with a dihedral angle of 89.1 (5)°. The two tolyl groups are twisted out of their connected terpyridyl moieties by 35.62 (4)° and 20.23 (6)°, respectively. Both perchlorate anions are disordered and were refined with two sets of disordered O atom positions for each. There are several C—H···O hydrogen bonds (Steiner, 1997) between the ttp ligand and the neighbouring perchloartes which involve the cations and counter-anions (Table 1).