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In the title complex, [Mn(C22H17N3)2](ClO4)2, the MnN6 coordination geometry is distorted octa­hedral, involving the six N atoms of two 4′-(4-methyl­phenyl)-2,2′:6′,2′′-terpyridine (ttp) ligands. The two chelated ttp planes are almost perpendicular, with a dihedral angle of 89.1 (5)°. The packing involves inter­molecular C—H...O hydrogen bonds between the ttp ligands and perchlorate anions. The latter are disordered over two positions, one with almost equal occupancy and the other in a ratio of ca 0.7:0.3.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040391/gg2037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040391/gg2037Isup2.hkl
Contains datablock I

CCDC reference: 660147

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the numbering scheme and displacement ellipsoids drawn at the 20% probability level. Only one set of disordered positions for each perchlorate is displayed for clarity.
Bis[4'-(4-methylphenyl)-2,2':6',2''-terpyridine-κ3N,N', N'']manganese(II) bis(perchlorate) top
Crystal data top
[Mn(C22H17N3)2](ClO4)2F(000) = 1852
Mr = 900.61Dx = 1.417 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8356 reflections
a = 18.2372 (4) Åθ = 1.4–28.0°
b = 15.4778 (4) ŵ = 0.50 mm1
c = 15.9465 (4) ÅT = 293 K
β = 110.339 (2)°Block, yellow
V = 4220.60 (18) Å30.25 × 0.19 × 0.16 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer
8296 independent reflections
Radiation source: fine-focus sealed tube4836 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
φ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.885, Tmax = 0.924k = 1719
45630 measured reflectionsl = 1919
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H-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 parametersΔρmax = 0.44 e Å3
176 restraintsΔρmin = 0.46 e Å3
Crystal data top
[Mn(C22H17N3)2](ClO4)2V = 4220.60 (18) Å3
Mr = 900.61Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.2372 (4) ŵ = 0.50 mm1
b = 15.4778 (4) ÅT = 293 K
c = 15.9465 (4) Å0.25 × 0.19 × 0.16 mm
β = 110.339 (2)°
Data collection top
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 = 0.924Rint = 0.090
45630 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060176 restraints
wR(F2) = 0.204H-atom parameters constrained
S = 0.98Δρmax = 0.44 e Å3
8296 reflectionsΔρmin = 0.46 e Å3
644 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*/UeqOcc. (<1)
C10.7202 (3)0.6693 (3)0.4596 (3)0.0771 (15)
H10.77420.67470.47590.092*
C20.6874 (4)0.6750 (4)0.5240 (4)0.0880 (17)
H20.71850.68370.58350.106*
C30.6072 (4)0.6677 (4)0.4998 (4)0.0935 (18)
H30.58350.67070.54280.112*
C40.5628 (3)0.6559 (4)0.4110 (4)0.0846 (17)
H40.50870.65170.39350.102*
C50.5989 (3)0.6504 (3)0.3479 (3)0.0557 (12)
C60.5569 (3)0.6388 (3)0.2515 (3)0.0545 (11)
C70.4766 (3)0.6394 (3)0.2116 (3)0.0626 (13)
H70.44560.64810.24650.075*
C80.4413 (3)0.6272 (3)0.1198 (3)0.0644 (13)
C90.4919 (3)0.6151 (3)0.0721 (3)0.0632 (13)
H90.47120.60550.01080.076*
C100.5717 (3)0.6171 (3)0.1141 (3)0.0550 (12)
C110.6290 (3)0.6082 (3)0.0682 (3)0.0583 (12)
C120.6073 (3)0.5995 (3)0.0238 (3)0.0698 (14)
H120.55480.59680.05960.084*
C130.6650 (4)0.5951 (4)0.0612 (3)0.0809 (16)
H130.65160.58870.12270.097*
C140.7417 (3)0.6002 (4)0.0077 (4)0.0814 (16)
H140.78120.59770.03190.098*
C150.7593 (3)0.6092 (3)0.0832 (3)0.0757 (15)
H150.81160.61330.11950.091*
C160.3552 (3)0.6262 (3)0.0749 (4)0.0742 (15)
C170.3057 (3)0.6089 (3)0.1227 (4)0.0838 (17)
H170.32660.60050.18420.101*
C180.2248 (3)0.6042 (4)0.0786 (5)0.096 (2)
H180.19240.59400.11150.115*
C190.1920 (4)0.6145 (4)0.0137 (6)0.105 (2)
C200.2407 (4)0.6317 (5)0.0603 (5)0.125 (3)
H200.21960.63880.12200.150*
C210.3212 (4)0.6388 (4)0.0173 (5)0.112 (2)
H210.35280.65220.05040.134*
C220.1048 (4)0.6031 (6)0.0606 (6)0.164 (4)
H22A0.09070.54430.05450.247*
H22B0.09130.61680.12290.247*
H22C0.07720.64100.03420.247*
C230.7323 (3)0.8362 (4)0.2579 (3)0.0607 (12)
H230.67900.83010.24660.073*
C240.7615 (3)0.9169 (4)0.2579 (3)0.0695 (14)
H240.72870.96470.24730.083*
C250.8405 (3)0.9271 (4)0.2737 (4)0.0836 (16)
H250.86180.98150.27300.100*
C260.8870 (3)0.8537 (4)0.2909 (4)0.0765 (15)
H260.94050.85850.30240.092*
C270.8542 (3)0.7738 (3)0.2908 (3)0.0526 (11)
C280.8998 (3)0.6925 (3)0.3100 (3)0.0511 (11)
C290.9783 (3)0.6870 (3)0.3250 (3)0.0569 (12)
H291.00570.73680.32140.068*
C301.0176 (3)0.6093 (3)0.3452 (3)0.0576 (12)
C310.9733 (3)0.5368 (3)0.3503 (3)0.0643 (13)
H310.99700.48290.36460.077*
C320.8946 (3)0.5458 (3)0.3341 (3)0.0582 (12)
C330.8412 (3)0.4725 (3)0.3363 (3)0.0661 (13)
C340.8671 (4)0.3912 (4)0.3655 (5)0.097 (2)
H340.92020.37840.38470.117*
C350.8139 (4)0.3288 (4)0.3663 (5)0.113 (2)
H350.83070.27310.38530.135*
C360.7364 (4)0.3486 (4)0.3390 (5)0.105 (2)
H360.69970.30720.33970.126*
C370.7140 (3)0.4313 (4)0.3104 (4)0.0926 (18)
H370.66110.44490.29110.111*
C381.1023 (3)0.6038 (3)0.3604 (3)0.0613 (13)
C391.1345 (3)0.6565 (3)0.3126 (3)0.0739 (15)
H391.10230.69300.26890.089*
C401.2146 (3)0.6558 (4)0.3292 (4)0.0788 (15)
H401.23480.69170.29590.095*
C411.2643 (3)0.6038 (4)0.3929 (4)0.0776 (15)
C421.2313 (3)0.5503 (4)0.4403 (4)0.0874 (18)
H421.26360.51440.48460.105*
C431.1523 (3)0.5490 (4)0.4233 (3)0.0802 (16)
H431.13180.51070.45440.096*
C441.3513 (3)0.6065 (4)0.4123 (4)0.108 (2)
H44A1.36190.63880.36640.162*
H44B1.37080.54860.41370.162*
H44C1.37670.63360.46920.162*
Mn10.73059 (4)0.63041 (5)0.26895 (4)0.0557 (3)
N10.6769 (2)0.6561 (2)0.3723 (2)0.0605 (10)
N20.6036 (2)0.6273 (2)0.2033 (2)0.0541 (9)
N30.7050 (2)0.6124 (2)0.1215 (2)0.0605 (10)
N40.7769 (2)0.7645 (2)0.2734 (2)0.0548 (9)
N50.8585 (2)0.6222 (2)0.3133 (2)0.0542 (9)
N60.7649 (2)0.4934 (3)0.3088 (3)0.0692 (11)
Cl1A0.9435 (4)0.7412 (4)0.5646 (5)0.103 (2)0.505 (7)
Cl2A0.50345 (19)0.9028 (2)0.1940 (2)0.0725 (12)0.739 (9)
O1A0.8876 (6)0.7478 (8)0.6104 (6)0.155 (4)0.505 (7)
O2A1.0179 (6)0.7748 (10)0.6119 (10)0.200 (7)0.505 (7)
O3A0.9374 (5)0.6574 (5)0.5272 (6)0.119 (4)0.505 (7)
O4A0.9015 (7)0.8002 (7)0.4925 (7)0.164 (5)0.505 (7)
O5A0.5726 (3)0.9584 (4)0.2206 (5)0.106 (2)0.739 (9)
O6A0.5221 (5)0.8284 (4)0.1549 (6)0.131 (3)0.739 (9)
O7A0.4830 (5)0.8790 (7)0.2698 (5)0.134 (3)0.739 (9)
O8A0.4411 (3)0.9499 (5)0.1343 (4)0.121 (3)0.739 (9)
Cl1B0.9560 (5)0.7580 (7)0.5794 (7)0.164 (4)0.495 (7)
Cl2B0.5018 (10)0.8960 (11)0.2035 (11)0.167 (7)0.261 (9)
O1B0.9831 (7)0.7036 (7)0.6559 (6)0.146 (4)0.495 (7)
O2B1.0134 (6)0.7686 (8)0.5385 (8)0.151 (5)0.495 (7)
O3B0.8915 (9)0.7227 (15)0.5115 (11)0.291 (9)0.495 (7)
O4B0.9392 (9)0.8412 (9)0.6074 (10)0.228 (6)0.495 (7)
O5B0.5485 (16)0.9575 (18)0.1749 (18)0.197 (10)0.261 (9)
O6B0.5510 (11)0.8237 (12)0.2409 (19)0.168 (9)0.261 (9)
O7B0.4791 (13)0.9387 (15)0.2706 (14)0.139 (8)0.261 (9)
O8B0.4373 (11)0.867 (2)0.1298 (13)0.176 (9)0.261 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.087 (4)0.077 (4)0.063 (3)0.000 (3)0.021 (3)0.004 (3)
C20.120 (5)0.088 (4)0.061 (3)0.009 (4)0.037 (4)0.001 (3)
C30.129 (6)0.091 (5)0.085 (4)0.001 (4)0.069 (4)0.002 (3)
C40.088 (4)0.099 (5)0.077 (4)0.006 (3)0.041 (3)0.010 (3)
C50.062 (3)0.053 (3)0.060 (3)0.006 (2)0.031 (2)0.001 (2)
C60.056 (3)0.049 (3)0.062 (3)0.001 (2)0.026 (2)0.000 (2)
C70.056 (3)0.059 (3)0.082 (3)0.005 (2)0.036 (3)0.003 (3)
C80.065 (3)0.045 (3)0.082 (3)0.004 (2)0.023 (3)0.004 (2)
C90.066 (3)0.058 (3)0.062 (3)0.009 (2)0.019 (2)0.005 (2)
C100.060 (3)0.050 (3)0.056 (3)0.012 (2)0.021 (2)0.006 (2)
C110.070 (3)0.055 (3)0.057 (3)0.014 (2)0.031 (2)0.005 (2)
C120.076 (3)0.071 (4)0.068 (3)0.021 (3)0.032 (3)0.013 (3)
C130.108 (5)0.082 (4)0.066 (3)0.021 (3)0.046 (3)0.017 (3)
C140.095 (4)0.083 (4)0.085 (4)0.019 (3)0.056 (3)0.022 (3)
C150.073 (3)0.092 (4)0.073 (3)0.010 (3)0.039 (3)0.015 (3)
C160.059 (3)0.057 (3)0.096 (4)0.004 (3)0.014 (3)0.011 (3)
C170.059 (3)0.080 (4)0.115 (4)0.001 (3)0.034 (3)0.006 (3)
C180.059 (4)0.074 (4)0.155 (6)0.002 (3)0.038 (4)0.012 (4)
C190.061 (4)0.084 (5)0.147 (6)0.005 (3)0.009 (4)0.013 (4)
C200.076 (5)0.131 (7)0.136 (6)0.001 (4)0.004 (4)0.050 (5)
C210.073 (4)0.121 (6)0.126 (5)0.006 (4)0.015 (4)0.047 (4)
C220.065 (4)0.175 (9)0.206 (9)0.011 (5)0.014 (5)0.010 (7)
C230.066 (3)0.062 (4)0.063 (3)0.010 (3)0.034 (2)0.003 (2)
C240.074 (4)0.061 (4)0.082 (3)0.019 (3)0.038 (3)0.011 (3)
C250.089 (4)0.049 (4)0.126 (5)0.004 (3)0.054 (4)0.007 (3)
C260.055 (3)0.062 (4)0.116 (4)0.002 (3)0.034 (3)0.007 (3)
C270.053 (3)0.053 (3)0.056 (3)0.001 (2)0.025 (2)0.001 (2)
C280.054 (3)0.050 (3)0.051 (2)0.001 (2)0.021 (2)0.001 (2)
C290.054 (3)0.053 (3)0.066 (3)0.002 (2)0.024 (2)0.003 (2)
C300.059 (3)0.057 (3)0.059 (3)0.003 (2)0.022 (2)0.001 (2)
C310.060 (3)0.055 (3)0.080 (3)0.011 (3)0.026 (2)0.003 (3)
C320.060 (3)0.053 (3)0.065 (3)0.002 (2)0.025 (2)0.000 (2)
C330.059 (3)0.058 (4)0.084 (3)0.000 (3)0.030 (3)0.001 (3)
C340.083 (4)0.054 (4)0.160 (6)0.010 (3)0.050 (4)0.015 (4)
C350.111 (6)0.059 (4)0.175 (7)0.007 (4)0.059 (5)0.019 (4)
C360.088 (5)0.069 (5)0.167 (6)0.015 (4)0.058 (4)0.009 (4)
C370.072 (4)0.067 (4)0.147 (5)0.011 (3)0.049 (4)0.010 (4)
C380.054 (3)0.064 (3)0.069 (3)0.003 (2)0.025 (2)0.003 (3)
C390.057 (3)0.079 (4)0.089 (4)0.007 (3)0.029 (3)0.014 (3)
C400.062 (3)0.087 (4)0.089 (4)0.000 (3)0.029 (3)0.007 (3)
C410.054 (3)0.090 (4)0.089 (4)0.000 (3)0.026 (3)0.010 (3)
C420.065 (4)0.107 (5)0.082 (4)0.026 (3)0.015 (3)0.012 (3)
C430.068 (4)0.092 (4)0.081 (3)0.016 (3)0.028 (3)0.016 (3)
C440.057 (4)0.144 (6)0.125 (5)0.005 (4)0.033 (3)0.009 (4)
Mn10.0487 (4)0.0608 (5)0.0601 (4)0.0020 (3)0.0222 (3)0.0027 (3)
N10.067 (3)0.061 (3)0.057 (2)0.003 (2)0.025 (2)0.0038 (19)
N20.059 (2)0.054 (2)0.054 (2)0.0068 (18)0.0249 (18)0.0054 (17)
N30.059 (2)0.067 (3)0.060 (2)0.010 (2)0.027 (2)0.0097 (19)
N40.053 (2)0.059 (3)0.058 (2)0.0064 (19)0.0251 (17)0.0008 (18)
N50.059 (2)0.046 (3)0.061 (2)0.001 (2)0.0239 (18)0.0036 (18)
N60.063 (3)0.056 (3)0.095 (3)0.007 (2)0.037 (2)0.003 (2)
Cl1A0.064 (3)0.143 (4)0.086 (3)0.013 (3)0.006 (2)0.028 (3)
Cl2A0.065 (2)0.077 (2)0.0813 (19)0.0177 (15)0.0326 (15)0.0062 (14)
O1A0.154 (8)0.206 (11)0.118 (7)0.024 (8)0.065 (6)0.052 (7)
O2A0.100 (7)0.234 (13)0.211 (13)0.002 (8)0.017 (7)0.091 (11)
O3A0.098 (6)0.144 (7)0.096 (6)0.034 (5)0.008 (5)0.042 (5)
O4A0.158 (9)0.174 (9)0.138 (8)0.041 (8)0.025 (6)0.035 (7)
O5A0.082 (4)0.100 (5)0.127 (5)0.011 (3)0.024 (3)0.002 (4)
O6A0.168 (7)0.068 (4)0.194 (7)0.002 (4)0.111 (6)0.016 (4)
O7A0.110 (5)0.213 (10)0.094 (4)0.014 (6)0.056 (4)0.030 (5)
O8A0.094 (4)0.132 (6)0.115 (4)0.031 (4)0.010 (3)0.026 (4)
Cl1B0.086 (5)0.301 (10)0.098 (4)0.035 (5)0.024 (4)0.063 (5)
Cl2B0.116 (12)0.184 (15)0.182 (14)0.005 (9)0.029 (9)0.003 (11)
O1B0.160 (9)0.198 (10)0.123 (7)0.022 (7)0.104 (6)0.049 (6)
O2B0.128 (8)0.193 (11)0.157 (9)0.048 (7)0.079 (7)0.047 (8)
O3B0.176 (11)0.421 (19)0.226 (13)0.096 (14)0.006 (10)0.041 (13)
O4B0.201 (12)0.299 (13)0.179 (11)0.104 (11)0.060 (9)0.021 (9)
O5B0.177 (19)0.208 (19)0.20 (2)0.025 (15)0.061 (14)0.009 (16)
O6B0.111 (13)0.149 (15)0.215 (19)0.007 (10)0.020 (12)0.020 (13)
O7B0.105 (13)0.121 (16)0.167 (15)0.005 (11)0.018 (10)0.009 (12)
O8B0.126 (14)0.22 (2)0.152 (15)0.008 (13)0.017 (11)0.020 (14)
Geometric parameters (Å, º) top
C1—N11.357 (6)C28—N51.334 (5)
C1—C21.359 (7)C28—C291.370 (6)
C1—H10.9300C29—C301.380 (6)
C2—C31.382 (7)C29—H290.9300
C2—H20.9300C30—C311.403 (6)
C3—C41.377 (7)C30—C381.480 (6)
C3—H30.9300C31—C321.373 (6)
C4—C51.383 (7)C31—H310.9300
C4—H40.9300C32—N51.339 (5)
C5—N11.341 (5)C32—C331.503 (6)
C5—C61.472 (6)C33—N61.346 (6)
C6—N21.343 (5)C33—C341.368 (7)
C6—C71.379 (6)C34—C351.373 (8)
C7—C81.392 (7)C34—H340.9300
C7—H70.9300C35—C361.360 (8)
C8—C91.398 (7)C35—H350.9300
C8—C161.481 (7)C36—C371.372 (8)
C9—C101.374 (6)C36—H360.9300
C9—H90.9300C37—N61.342 (6)
C10—N21.346 (5)C37—H370.9300
C10—C111.476 (6)C38—C391.379 (7)
C11—N31.352 (6)C38—C431.386 (6)
C11—C121.386 (6)C39—C401.391 (6)
C12—C131.380 (7)C39—H390.9300
C12—H120.9300C40—C411.364 (7)
C13—C141.365 (7)C40—H400.9300
C13—H130.9300C41—C421.391 (8)
C14—C151.377 (7)C41—C441.508 (7)
C14—H140.9300C42—C431.371 (7)
C15—N31.333 (6)C42—H420.9300
C15—H150.9300C43—H430.9300
C16—C171.395 (7)C44—H44A0.9600
C16—C211.397 (8)C44—H44B0.9600
C17—C181.397 (7)C44—H44C0.9600
C17—H170.9300Mn1—N22.185 (4)
C18—C191.392 (9)Mn1—N52.193 (4)
C18—H180.9300Mn1—N12.225 (4)
C19—C201.368 (10)Mn1—N42.233 (4)
C19—C221.514 (8)Mn1—N62.240 (4)
C20—C211.392 (8)Mn1—N32.250 (4)
C20—H200.9300Cl1A—O2A1.404 (8)
C21—H210.9300Cl1A—O3A1.416 (8)
C22—H22A0.9600Cl1A—O1A1.448 (8)
C22—H22B0.9600Cl1A—O4A1.459 (8)
C22—H22C0.9600Cl2A—O6A1.406 (6)
C23—N41.347 (6)Cl2A—O8A1.407 (5)
C23—C241.358 (7)Cl2A—O7A1.431 (6)
C23—H230.9300Cl2A—O5A1.462 (5)
C24—C251.382 (7)Cl1B—O3B1.403 (9)
C24—H240.9300Cl1B—O1B1.422 (9)
C25—C261.388 (7)Cl1B—O2B1.423 (9)
C25—H250.9300Cl1B—O4B1.430 (9)
C26—C271.373 (6)Cl2B—O8B1.416 (10)
C26—H260.9300Cl2B—O6B1.430 (10)
C27—N41.347 (5)Cl2B—O7B1.435 (10)
C27—C281.481 (6)Cl2B—O5B1.452 (10)
N1—C1—C2122.2 (5)C31—C32—C33124.2 (4)
N1—C1—H1118.9N6—C33—C34121.8 (5)
C2—C1—H1118.9N6—C33—C32114.7 (4)
C1—C2—C3119.0 (5)C34—C33—C32123.5 (5)
C1—C2—H2120.5C33—C34—C35119.3 (6)
C3—C2—H2120.5C33—C34—H34120.3
C4—C3—C2119.0 (5)C35—C34—H34120.3
C4—C3—H3120.5C36—C35—C34119.8 (6)
C2—C3—H3120.5C36—C35—H35120.1
C3—C4—C5119.9 (5)C34—C35—H35120.1
C3—C4—H4120.1C35—C36—C37118.2 (6)
C5—C4—H4120.1C35—C36—H36120.9
N1—C5—C4120.7 (4)C37—C36—H36120.9
N1—C5—C6115.2 (4)N6—C37—C36123.1 (5)
C4—C5—C6124.1 (5)N6—C37—H37118.4
N2—C6—C7121.3 (4)C36—C37—H37118.4
N2—C6—C5114.2 (4)C39—C38—C43117.6 (5)
C7—C6—C5124.4 (4)C39—C38—C30119.7 (4)
C6—C7—C8120.9 (5)C43—C38—C30122.7 (5)
C6—C7—H7119.5C38—C39—C40120.7 (5)
C8—C7—H7119.5C38—C39—H39119.6
C7—C8—C9116.0 (4)C40—C39—H39119.6
C7—C8—C16122.3 (5)C41—C40—C39121.9 (5)
C9—C8—C16121.7 (5)C41—C40—H40119.0
C10—C9—C8121.3 (4)C39—C40—H40119.0
C10—C9—H9119.3C40—C41—C42117.0 (5)
C8—C9—H9119.3C40—C41—C44121.1 (6)
N2—C10—C9120.8 (4)C42—C41—C44121.9 (5)
N2—C10—C11114.5 (4)C43—C42—C41121.6 (5)
C9—C10—C11124.7 (4)C43—C42—H42119.2
N3—C11—C12121.6 (4)C41—C42—H42119.2
N3—C11—C10115.6 (4)C42—C43—C38121.1 (5)
C12—C11—C10122.8 (4)C42—C43—H43119.5
C13—C12—C11118.8 (5)C38—C43—H43119.5
C13—C12—H12120.6N2—Mn1—N5169.82 (13)
C11—C12—H12120.6N2—Mn1—N172.13 (13)
C14—C13—C12119.7 (5)N5—Mn1—N1117.65 (13)
C14—C13—H13120.1N2—Mn1—N4111.21 (13)
C12—C13—H13120.1N5—Mn1—N472.26 (14)
C13—C14—C15118.5 (5)N1—Mn1—N494.00 (13)
C13—C14—H14120.7N2—Mn1—N6105.07 (14)
C15—C14—H14120.7N5—Mn1—N672.12 (14)
N3—C15—C14123.2 (5)N1—Mn1—N696.33 (14)
N3—C15—H15118.4N4—Mn1—N6143.71 (14)
C14—C15—H15118.4N2—Mn1—N372.32 (14)
C17—C16—C21117.8 (5)N5—Mn1—N398.07 (14)
C17—C16—C8121.1 (5)N1—Mn1—N3144.22 (14)
C21—C16—C8121.0 (6)N4—Mn1—N394.98 (13)
C16—C17—C18120.4 (6)N6—Mn1—N396.61 (14)
C16—C17—H17119.8C5—N1—C1119.2 (4)
C18—C17—H17119.8C5—N1—Mn1118.0 (3)
C19—C18—C17121.1 (6)C1—N1—Mn1122.5 (3)
C19—C18—H18119.5C6—N2—C10119.5 (4)
C17—C18—H18119.5C6—N2—Mn1120.0 (3)
C20—C19—C18118.4 (6)C10—N2—Mn1120.4 (3)
C20—C19—C22121.5 (7)C15—N3—C11118.1 (4)
C18—C19—C22120.1 (7)C15—N3—Mn1124.6 (3)
C19—C20—C21121.3 (7)C11—N3—Mn1117.3 (3)
C19—C20—H20119.3C27—N4—C23118.2 (4)
C21—C20—H20119.3C27—N4—Mn1117.6 (3)
C20—C21—C16120.9 (7)C23—N4—Mn1124.2 (3)
C20—C21—H21119.5C28—N5—C32119.6 (4)
C16—C21—H21119.5C28—N5—Mn1119.5 (3)
N4—C23—C24123.1 (5)C32—N5—Mn1120.5 (3)
N4—C23—H23118.5C37—N6—C33117.7 (5)
C24—C23—H23118.5C37—N6—Mn1123.9 (4)
C23—C24—C25119.3 (5)C33—N6—Mn1118.3 (3)
C23—C24—H24120.4O2A—Cl1A—O3A119.0 (8)
C25—C24—H24120.4O2A—Cl1A—O1A114.9 (9)
C24—C25—C26118.0 (5)O3A—Cl1A—O1A108.1 (7)
C24—C25—H25121.0O2A—Cl1A—O4A109.7 (9)
C26—C25—H25121.0O3A—Cl1A—O4A107.5 (8)
C27—C26—C25120.0 (5)O1A—Cl1A—O4A94.8 (7)
C27—C26—H26120.0O6A—Cl2A—O8A112.8 (5)
C25—C26—H26120.0O6A—Cl2A—O7A109.8 (5)
N4—C27—C26121.4 (4)O8A—Cl2A—O7A108.6 (5)
N4—C27—C28115.0 (4)O6A—Cl2A—O5A107.1 (4)
C26—C27—C28123.5 (4)O8A—Cl2A—O5A107.7 (4)
N5—C28—C29120.9 (4)O7A—Cl2A—O5A111.0 (5)
N5—C28—C27114.7 (4)O3B—Cl1B—O1B112.3 (12)
C29—C28—C27124.4 (4)O3B—Cl1B—O2B104.1 (10)
C28—C29—C30121.4 (4)O1B—Cl1B—O2B111.7 (8)
C28—C29—H29119.3O3B—Cl1B—O4B112.2 (11)
C30—C29—H29119.3O1B—Cl1B—O4B108.3 (9)
C29—C30—C31116.6 (4)O2B—Cl1B—O4B108.1 (10)
C29—C30—C38121.1 (4)O8B—Cl2B—O6B108.5 (13)
C31—C30—C38122.3 (4)O8B—Cl2B—O7B113.2 (13)
C32—C31—C30119.6 (4)O6B—Cl2B—O7B110.5 (13)
C32—C31—H31120.2O8B—Cl2B—O5B110.9 (14)
C30—C31—H31120.2O6B—Cl2B—O5B106.9 (13)
N5—C32—C31121.9 (4)O7B—Cl2B—O5B106.6 (13)
N5—C32—C33113.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O3B0.932.153.055 (15)165
C3—H3···O6Ai0.932.423.347 (9)176
C13—H13···O5Aii0.932.523.400 (9)158
C15—H15···O4Bii0.932.503.260 (16)139
C22—H22C···O2Biii0.962.373.324 (14)177
C23—H23···O6B0.932.313.23 (2)171
C34—H34···O3Aiv0.932.553.458 (11)167
C34—H34···O1Biv0.932.443.223 (12)142
C37—H37···O8Av0.932.543.255 (9)134
C37—H37···O7Bv0.932.403.31 (2)164
C39—H39···O2Aii0.932.493.341 (12)152
C44—H44C···O8Bvi0.962.413.30 (2)153
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x1, y+3/2, z1/2; (iv) x+2, y+1, z+1; (v) x+1, y1/2, z+1/2; (vi) x+1, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Mn(C22H17N3)2](ClO4)2
Mr900.61
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)18.2372 (4), 15.4778 (4), 15.9465 (4)
β (°) 110.339 (2)
V3)4220.60 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.50
Crystal size (mm)0.25 × 0.19 × 0.16
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.885, 0.924
No. of measured, independent and
observed [I > 2σ(I)] reflections
45630, 8296, 4836
Rint0.090
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.204, 0.98
No. of reflections8296
No. of parameters644
No. of restraints176
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.46

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O3B0.932.153.055 (15)165
C3—H3···O6Ai0.932.423.347 (9)176
C13—H13···O5Aii0.932.523.400 (9)158
C15—H15···O4Bii0.932.503.260 (16)139
C22—H22C···O2Biii0.962.373.324 (14)177
C23—H23···O6B0.932.313.23 (2)171
C34—H34···O3Aiv0.932.553.458 (11)167
C34—H34···O1Biv0.932.443.223 (12)142
C37—H37···O8Av0.932.543.255 (9)134
C37—H37···O7Bv0.932.403.31 (2)164
C39—H39···O2Aii0.932.493.341 (12)152
C44—H44C···O8Bvi0.962.413.30 (2)153
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x1, y+3/2, z1/2; (iv) x+2, y+1, z+1; (v) x+1, y1/2, z+1/2; (vi) x+1, y+3/2, z+1/2.
 

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