Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056644/kp2141sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056644/kp2141Isup2.hkl |
CCDC reference: 672664
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.121
- Data-to-parameter ratio = 22.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1600 Deg. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - Cl1 .. 7.74 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C43
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 2.18 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn2 (2) 2.20
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 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 2 ALERT type 5 Informative message, check
For related literature, see: Babik & Fink (2003); Esteruelas et al. (2003); Fan et al. (2005); Gibson et al. (2001); Jiang et al. (2005); Marganian et al. (1995); Mentes et al. (2001); Nishio (2004); Pradhan et al. (2003); Reardon et al. (2002); Trivedi et al. (2007).
For related literature, see: Štefanić et al. (2006).
The ligand Plep (2,6-bis[(1-phenylimino)ethyl]pyridine) was prepared in high yield from condensation of two equivalents of aniline with one equivalent of 2,6-diacetylpyridine in methanol according to the reported paper (Babik et al., 2003). The title complex was synthesized in good yield by treating MnCl2·4H2O with Plep in a mixture solution. To a solution of Plep (0.5 mmol) in a methanol-dichloromethane mixture (1:1 v/v; 10 ml), a solution of MnCl2·4H2O (0.5 mmol) in methanol (10 ml) was added dropwise at 353 K. After stirring for 2 h, the mixture was allowed to cool to room temperature and filtrated. The resultant filtrate was left to stand to evaporate slowly at room temperature. Red single crystals of (I) suitable for X-ray structure analysis were obtained after a week (yield 72%).
Hydrogen atoms attached to carbon atoms were positioned geometrically and treated as riding, with C—H = 0.95 Å, and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
[MnCl2(C21H19N3)]·0.5CH2Cl2 | V = 2248.6 (9) Å3 |
Mr = 481.70 | Z = 4 |
Triclinic, P1 | F(000) = 984 |
Hall symbol: -P 1 | Dx = 1.423 Mg m−3 |
a = 9.007 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.834 (3) Å | θ = 2.1–29.2° |
c = 20.139 (5) Å | µ = 0.96 mm−1 |
α = 79.582 (16)° | T = 273 K |
β = 79.230 (16)° | Block, yellow |
γ = 86.698 (16)° | 0.42 × 0.38 × 0.22 mm |
Bruker SMART CCD area-detector diffractometer | 11765 independent reflections |
Radiation source: fine-focus sealed tube | 7352 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
phi and ω scans | θmax = 29.2°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.678, Tmax = 0.808 | k = −17→17 |
25241 measured reflections | l = −27→27 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0593P)2] where P = (Fo2 + 2Fc2)/3 |
11765 reflections | (Δ/σ)max = 0.001 |
518 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
[MnCl2(C21H19N3)]·0.5CH2Cl2 | γ = 86.698 (16)° |
Mr = 481.70 | V = 2248.6 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.007 (2) Å | Mo Kα radiation |
b = 12.834 (3) Å | µ = 0.96 mm−1 |
c = 20.139 (5) Å | T = 273 K |
α = 79.582 (16)° | 0.42 × 0.38 × 0.22 mm |
β = 79.230 (16)° |
Bruker SMART CCD area-detector diffractometer | 11765 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7352 reflections with I > 2σ(I) |
Tmin = 0.678, Tmax = 0.808 | Rint = 0.034 |
25241 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.41 e Å−3 |
11765 reflections | Δρmin = −0.51 e Å−3 |
518 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 | ||
Mn1 | 0.35408 (4) | 0.98111 (3) | 0.193164 (17) | 0.04029 (10) | |
Mn2 | 0.67731 (4) | 0.39071 (3) | 0.267042 (17) | 0.04065 (10) | |
Cl1 | 0.29641 (8) | 1.11792 (5) | 0.25620 (3) | 0.06043 (18) | |
Cl2 | 0.18473 (7) | 0.94877 (6) | 0.12561 (3) | 0.06250 (19) | |
Cl3 | 0.78757 (8) | 0.47289 (5) | 0.34005 (3) | 0.05625 (17) | |
Cl4 | 0.51865 (9) | 0.49654 (6) | 0.20323 (4) | 0.0730 (2) | |
N1 | 0.3060 (2) | 0.83597 (15) | 0.27966 (10) | 0.0459 (5) | |
N2 | 0.5600 (2) | 0.88241 (14) | 0.19373 (9) | 0.0415 (4) | |
N3 | 0.5413 (2) | 1.06172 (15) | 0.10978 (9) | 0.0432 (4) | |
N4 | 0.8875 (2) | 0.37159 (16) | 0.18821 (9) | 0.0469 (5) | |
N5 | 0.7246 (2) | 0.22045 (14) | 0.26773 (9) | 0.0400 (4) | |
N6 | 0.5066 (2) | 0.29645 (15) | 0.35063 (9) | 0.0442 (4) | |
C1 | 0.1026 (3) | 0.8939 (2) | 0.36272 (13) | 0.0524 (6) | |
H1A | 0.1568 | 0.9540 | 0.3614 | 0.063* | |
C2 | −0.0366 (3) | 0.8788 (2) | 0.40499 (13) | 0.0606 (7) | |
H2A | −0.0749 | 0.9280 | 0.4330 | 0.073* | |
C3 | −0.1182 (3) | 0.7924 (2) | 0.40592 (15) | 0.0641 (7) | |
H3A | −0.2115 | 0.7823 | 0.4348 | 0.077* | |
C4 | −0.0632 (3) | 0.7205 (2) | 0.36453 (16) | 0.0675 (8) | |
H4A | −0.1201 | 0.6622 | 0.3648 | 0.081* | |
C5 | 0.0767 (3) | 0.7338 (2) | 0.32223 (14) | 0.0618 (7) | |
H5A | 0.1133 | 0.6849 | 0.2938 | 0.074* | |
C6 | 0.1615 (3) | 0.81979 (19) | 0.32230 (12) | 0.0468 (6) | |
C7 | 0.4155 (3) | 0.76982 (18) | 0.28844 (12) | 0.0493 (6) | |
C8 | 0.4137 (4) | 0.6754 (2) | 0.34480 (15) | 0.0736 (9) | |
H8A | 0.3219 | 0.6770 | 0.3777 | 0.110* | |
H8B | 0.4988 | 0.6772 | 0.3670 | 0.110* | |
H8C | 0.4191 | 0.6116 | 0.3258 | 0.110* | |
C9 | 0.5596 (3) | 0.79176 (18) | 0.23885 (12) | 0.0452 (5) | |
C10 | 0.6860 (3) | 0.7250 (2) | 0.23775 (15) | 0.0597 (7) | |
H10A | 0.6848 | 0.6622 | 0.2692 | 0.072* | |
C11 | 0.8119 (3) | 0.7522 (2) | 0.19015 (16) | 0.0629 (7) | |
H11A | 0.8974 | 0.7078 | 0.1887 | 0.075* | |
C12 | 0.8130 (3) | 0.8461 (2) | 0.14377 (14) | 0.0556 (6) | |
H12A | 0.8985 | 0.8656 | 0.1110 | 0.067* | |
C13 | 0.6840 (3) | 0.91029 (18) | 0.14731 (11) | 0.0428 (5) | |
C14 | 0.6706 (3) | 1.01542 (19) | 0.10174 (11) | 0.0431 (5) | |
C15 | 0.8071 (3) | 1.0581 (3) | 0.05254 (13) | 0.0656 (8) | |
H15A | 0.7916 | 1.1324 | 0.0369 | 0.098* | |
H15B | 0.8245 | 1.0216 | 0.0140 | 0.098* | |
H15C | 0.8933 | 1.0476 | 0.0750 | 0.098* | |
C16 | 0.5139 (3) | 1.16236 (18) | 0.06797 (12) | 0.0456 (5) | |
C17 | 0.4990 (4) | 1.1675 (2) | 0.00081 (14) | 0.0649 (8) | |
H17A | 0.5132 | 1.1070 | −0.0192 | 0.078* | |
C18 | 0.4625 (4) | 1.2638 (3) | −0.03660 (16) | 0.0795 (10) | |
H18A | 0.4505 | 1.2676 | −0.0819 | 0.095* | |
C19 | 0.4439 (3) | 1.3538 (2) | −0.00793 (18) | 0.0748 (9) | |
H19A | 0.4202 | 1.4183 | −0.0337 | 0.090* | |
C20 | 0.4601 (4) | 1.3486 (2) | 0.05816 (17) | 0.0723 (8) | |
H20A | 0.4476 | 1.4096 | 0.0776 | 0.087* | |
C21 | 0.4951 (3) | 1.2528 (2) | 0.09685 (14) | 0.0594 (7) | |
H21A | 0.5060 | 1.2496 | 0.1422 | 0.071* | |
C22 | 1.0981 (3) | 0.4912 (2) | 0.16725 (16) | 0.0692 (8) | |
H22A | 1.1349 | 0.4509 | 0.2042 | 0.083* | |
C23 | 1.1739 (4) | 0.5794 (3) | 0.13071 (19) | 0.0850 (10) | |
H23A | 1.2624 | 0.5978 | 0.1427 | 0.102* | |
C24 | 1.1207 (4) | 0.6395 (3) | 0.07757 (19) | 0.0864 (10) | |
H24A | 1.1725 | 0.6990 | 0.0530 | 0.104* | |
C25 | 0.9915 (5) | 0.6126 (3) | 0.06016 (16) | 0.0916 (11) | |
H25A | 0.9556 | 0.6541 | 0.0233 | 0.110* | |
C26 | 0.9113 (4) | 0.5241 (3) | 0.09653 (14) | 0.0720 (8) | |
H26A | 0.8212 | 0.5073 | 0.0852 | 0.086* | |
C27 | 0.9686 (3) | 0.4623 (2) | 0.14951 (12) | 0.0502 (6) | |
C28 | 0.9344 (3) | 0.27781 (19) | 0.18030 (11) | 0.0445 (5) | |
C29 | 1.0691 (3) | 0.2511 (2) | 0.13030 (14) | 0.0658 (8) | |
H29A | 1.1044 | 0.3142 | 0.0992 | 0.099* | |
H29B | 1.0418 | 0.2009 | 0.1049 | 0.099* | |
H29C | 1.1478 | 0.2208 | 0.1546 | 0.099* | |
C30 | 0.8454 (3) | 0.18943 (19) | 0.22606 (11) | 0.0428 (5) | |
C31 | 0.8853 (3) | 0.0831 (2) | 0.22799 (12) | 0.0497 (6) | |
H31A | 0.9702 | 0.0626 | 0.1988 | 0.060* | |
C32 | 0.7970 (3) | 0.0084 (2) | 0.27390 (13) | 0.0561 (7) | |
H32A | 0.8215 | −0.0634 | 0.2758 | 0.067* | |
C33 | 0.6722 (3) | 0.04079 (19) | 0.31688 (13) | 0.0506 (6) | |
H33A | 0.6113 | −0.0085 | 0.3481 | 0.061* | |
C34 | 0.6392 (3) | 0.14914 (18) | 0.31264 (11) | 0.0426 (5) | |
C35 | 0.5134 (3) | 0.19527 (19) | 0.35903 (11) | 0.0424 (5) | |
C36 | 0.4090 (3) | 0.1228 (2) | 0.41136 (13) | 0.0565 (6) | |
H36A | 0.3307 | 0.1639 | 0.4348 | 0.085* | |
H36B | 0.4648 | 0.0823 | 0.4439 | 0.085* | |
H36C | 0.3647 | 0.0757 | 0.3890 | 0.085* | |
C37 | 0.3959 (3) | 0.35222 (18) | 0.39241 (12) | 0.0441 (5) | |
C38 | 0.4284 (3) | 0.3792 (2) | 0.45107 (13) | 0.0553 (6) | |
H38A | 0.5189 | 0.3559 | 0.4653 | 0.066* | |
C39 | 0.3277 (3) | 0.4405 (2) | 0.48881 (14) | 0.0657 (8) | |
H39A | 0.3502 | 0.4583 | 0.5285 | 0.079* | |
C40 | 0.1955 (3) | 0.4750 (2) | 0.46821 (17) | 0.0690 (8) | |
H40A | 0.1277 | 0.5167 | 0.4936 | 0.083* | |
C41 | 0.1622 (3) | 0.4480 (2) | 0.40971 (17) | 0.0695 (8) | |
H41A | 0.0713 | 0.4714 | 0.3959 | 0.083* | |
C42 | 0.2621 (3) | 0.3866 (2) | 0.37111 (14) | 0.0595 (7) | |
H42A | 0.2393 | 0.3689 | 0.3314 | 0.071* | |
Cl6 | 0.99171 (12) | 0.17671 (8) | 0.38588 (6) | 0.1018 (3) | |
Cl5 | 0.72467 (12) | 0.14750 (10) | 0.49217 (6) | 0.1190 (4) | |
C43 | 0.8709 (4) | 0.2322 (3) | 0.44971 (18) | 0.0885 (11) | |
H43A | 0.9287 | 0.2475 | 0.4827 | 0.106* | |
H43B | 0.8280 | 0.2985 | 0.4291 | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.03806 (19) | 0.0390 (2) | 0.04186 (19) | 0.00085 (14) | −0.00693 (15) | −0.00276 (14) |
Mn2 | 0.0428 (2) | 0.03747 (19) | 0.04098 (19) | 0.00176 (15) | −0.00385 (15) | −0.00964 (14) |
Cl1 | 0.0791 (5) | 0.0531 (4) | 0.0491 (3) | −0.0070 (3) | −0.0059 (3) | −0.0130 (3) |
Cl2 | 0.0499 (4) | 0.0848 (5) | 0.0605 (4) | 0.0028 (3) | −0.0144 (3) | −0.0298 (4) |
Cl3 | 0.0696 (4) | 0.0470 (4) | 0.0574 (4) | −0.0032 (3) | −0.0213 (3) | −0.0121 (3) |
Cl4 | 0.0699 (5) | 0.0828 (5) | 0.0667 (4) | 0.0132 (4) | −0.0267 (4) | −0.0038 (4) |
N1 | 0.0496 (12) | 0.0384 (11) | 0.0475 (11) | −0.0032 (9) | −0.0089 (9) | −0.0009 (9) |
N2 | 0.0405 (10) | 0.0401 (11) | 0.0449 (10) | 0.0007 (8) | −0.0101 (9) | −0.0076 (8) |
N3 | 0.0438 (11) | 0.0404 (11) | 0.0439 (10) | −0.0035 (9) | −0.0066 (9) | −0.0036 (8) |
N4 | 0.0459 (11) | 0.0478 (12) | 0.0439 (11) | 0.0017 (9) | −0.0027 (9) | −0.0064 (9) |
N5 | 0.0418 (10) | 0.0401 (10) | 0.0386 (10) | 0.0025 (8) | −0.0061 (8) | −0.0103 (8) |
N6 | 0.0437 (11) | 0.0417 (11) | 0.0468 (11) | −0.0028 (9) | −0.0026 (9) | −0.0120 (9) |
C1 | 0.0571 (16) | 0.0448 (14) | 0.0533 (14) | −0.0106 (12) | −0.0076 (12) | −0.0026 (11) |
C2 | 0.0630 (17) | 0.0587 (17) | 0.0544 (15) | −0.0043 (14) | 0.0007 (13) | −0.0056 (13) |
C3 | 0.0553 (16) | 0.0644 (19) | 0.0639 (17) | −0.0095 (14) | −0.0015 (14) | 0.0046 (14) |
C4 | 0.0642 (18) | 0.0578 (18) | 0.079 (2) | −0.0228 (14) | −0.0129 (16) | −0.0020 (15) |
C5 | 0.0661 (18) | 0.0535 (16) | 0.0653 (17) | −0.0138 (14) | −0.0055 (14) | −0.0117 (13) |
C6 | 0.0501 (14) | 0.0416 (13) | 0.0456 (13) | −0.0081 (11) | −0.0105 (11) | 0.0044 (10) |
C7 | 0.0605 (16) | 0.0365 (13) | 0.0499 (14) | −0.0014 (11) | −0.0140 (12) | −0.0003 (10) |
C8 | 0.078 (2) | 0.0533 (17) | 0.076 (2) | 0.0044 (15) | −0.0087 (16) | 0.0166 (15) |
C9 | 0.0509 (14) | 0.0342 (12) | 0.0515 (13) | 0.0019 (10) | −0.0148 (11) | −0.0054 (10) |
C10 | 0.0646 (18) | 0.0428 (15) | 0.0724 (18) | 0.0090 (13) | −0.0223 (15) | −0.0047 (13) |
C11 | 0.0535 (16) | 0.0557 (17) | 0.083 (2) | 0.0182 (13) | −0.0188 (15) | −0.0195 (15) |
C12 | 0.0443 (14) | 0.0606 (17) | 0.0638 (16) | 0.0062 (12) | −0.0096 (12) | −0.0186 (13) |
C13 | 0.0419 (13) | 0.0454 (13) | 0.0449 (12) | 0.0016 (10) | −0.0126 (10) | −0.0139 (10) |
C14 | 0.0400 (12) | 0.0535 (14) | 0.0373 (12) | −0.0054 (11) | −0.0063 (10) | −0.0109 (10) |
C15 | 0.0464 (15) | 0.093 (2) | 0.0502 (15) | −0.0072 (14) | −0.0017 (12) | 0.0020 (14) |
C16 | 0.0402 (12) | 0.0420 (13) | 0.0505 (14) | −0.0042 (10) | −0.0036 (10) | −0.0010 (11) |
C17 | 0.090 (2) | 0.0509 (16) | 0.0559 (16) | −0.0101 (15) | −0.0222 (15) | −0.0024 (13) |
C18 | 0.102 (3) | 0.071 (2) | 0.0669 (19) | −0.0221 (19) | −0.0379 (18) | 0.0134 (16) |
C19 | 0.068 (2) | 0.0527 (18) | 0.093 (2) | −0.0084 (15) | −0.0178 (18) | 0.0203 (17) |
C20 | 0.082 (2) | 0.0432 (16) | 0.081 (2) | −0.0026 (15) | 0.0051 (17) | −0.0039 (15) |
C21 | 0.0735 (19) | 0.0482 (16) | 0.0524 (15) | −0.0087 (13) | −0.0024 (13) | −0.0051 (12) |
C22 | 0.0572 (17) | 0.0667 (19) | 0.078 (2) | −0.0042 (14) | −0.0166 (15) | 0.0077 (15) |
C23 | 0.0566 (19) | 0.074 (2) | 0.114 (3) | −0.0117 (16) | −0.0070 (19) | 0.007 (2) |
C24 | 0.080 (2) | 0.071 (2) | 0.089 (2) | −0.0100 (19) | 0.014 (2) | 0.0105 (19) |
C25 | 0.116 (3) | 0.084 (2) | 0.0591 (19) | −0.001 (2) | −0.010 (2) | 0.0201 (17) |
C26 | 0.082 (2) | 0.077 (2) | 0.0534 (16) | −0.0032 (17) | −0.0150 (15) | 0.0025 (15) |
C27 | 0.0477 (14) | 0.0513 (15) | 0.0464 (13) | 0.0062 (11) | 0.0013 (11) | −0.0076 (11) |
C28 | 0.0428 (13) | 0.0506 (15) | 0.0396 (12) | 0.0081 (11) | −0.0086 (10) | −0.0082 (10) |
C29 | 0.0608 (17) | 0.0638 (18) | 0.0624 (17) | 0.0138 (14) | 0.0088 (13) | −0.0088 (14) |
C30 | 0.0444 (13) | 0.0476 (14) | 0.0389 (12) | 0.0062 (10) | −0.0090 (10) | −0.0143 (10) |
C31 | 0.0551 (15) | 0.0509 (15) | 0.0454 (13) | 0.0126 (12) | −0.0108 (11) | −0.0167 (11) |
C32 | 0.0729 (18) | 0.0424 (14) | 0.0591 (16) | 0.0070 (13) | −0.0206 (14) | −0.0185 (12) |
C33 | 0.0613 (16) | 0.0382 (13) | 0.0538 (14) | −0.0039 (11) | −0.0111 (12) | −0.0101 (11) |
C34 | 0.0465 (13) | 0.0430 (13) | 0.0420 (12) | −0.0033 (10) | −0.0120 (10) | −0.0125 (10) |
C35 | 0.0411 (12) | 0.0468 (14) | 0.0402 (12) | −0.0066 (10) | −0.0065 (10) | −0.0093 (10) |
C36 | 0.0606 (16) | 0.0530 (15) | 0.0531 (15) | −0.0113 (13) | −0.0036 (12) | −0.0053 (12) |
C37 | 0.0392 (12) | 0.0433 (13) | 0.0468 (13) | −0.0052 (10) | 0.0036 (10) | −0.0105 (10) |
C38 | 0.0465 (14) | 0.0660 (17) | 0.0536 (15) | 0.0008 (12) | −0.0014 (12) | −0.0202 (13) |
C39 | 0.0591 (18) | 0.078 (2) | 0.0592 (16) | −0.0128 (15) | 0.0119 (14) | −0.0289 (15) |
C40 | 0.0517 (17) | 0.0612 (18) | 0.086 (2) | −0.0069 (14) | 0.0236 (15) | −0.0270 (16) |
C41 | 0.0387 (14) | 0.071 (2) | 0.090 (2) | 0.0062 (13) | 0.0023 (14) | −0.0081 (17) |
C42 | 0.0469 (15) | 0.0693 (18) | 0.0630 (16) | −0.0022 (13) | −0.0078 (13) | −0.0148 (14) |
Cl6 | 0.0934 (7) | 0.0891 (7) | 0.1316 (8) | 0.0004 (5) | −0.0274 (6) | −0.0354 (6) |
Cl5 | 0.1017 (8) | 0.1494 (10) | 0.1039 (7) | −0.0284 (7) | −0.0426 (6) | 0.0162 (7) |
C43 | 0.105 (3) | 0.065 (2) | 0.099 (3) | 0.0036 (19) | −0.042 (2) | −0.0026 (18) |
Mn1—N2 | 2.1856 (19) | C17—C18 | 1.383 (4) |
Mn1—N3 | 2.291 (2) | C17—H17A | 0.9300 |
Mn1—N1 | 2.3084 (19) | C18—C19 | 1.371 (5) |
Mn1—Cl2 | 2.3244 (8) | C18—H18A | 0.9300 |
Mn1—Cl1 | 2.3279 (9) | C19—C20 | 1.355 (4) |
Mn2—N5 | 2.2001 (19) | C19—H19A | 0.9300 |
Mn2—N4 | 2.265 (2) | C20—C21 | 1.385 (4) |
Mn2—N6 | 2.274 (2) | C20—H20A | 0.9300 |
Mn2—Cl4 | 2.3174 (9) | C21—H21A | 0.9300 |
Mn2—Cl3 | 2.3426 (8) | C22—C27 | 1.371 (4) |
N1—C7 | 1.280 (3) | C22—C23 | 1.374 (4) |
N1—C6 | 1.423 (3) | C22—H22A | 0.9300 |
N2—C13 | 1.336 (3) | C23—C24 | 1.349 (4) |
N2—C9 | 1.340 (3) | C23—H23A | 0.9300 |
N3—C14 | 1.273 (3) | C24—C25 | 1.357 (5) |
N3—C16 | 1.444 (3) | C24—H24A | 0.9300 |
N4—C28 | 1.280 (3) | C25—C26 | 1.395 (5) |
N4—C27 | 1.433 (3) | C25—H25A | 0.9300 |
N5—C34 | 1.330 (3) | C26—C27 | 1.373 (4) |
N5—C30 | 1.333 (3) | C26—H26A | 0.9300 |
N6—C35 | 1.278 (3) | C28—C29 | 1.491 (3) |
N6—C37 | 1.427 (3) | C28—C30 | 1.493 (3) |
C1—C2 | 1.380 (4) | C29—H29A | 0.9600 |
C1—C6 | 1.382 (4) | C29—H29B | 0.9600 |
C1—H1A | 0.9300 | C29—H29C | 0.9600 |
C2—C3 | 1.361 (4) | C30—C31 | 1.386 (3) |
C2—H2A | 0.9300 | C31—C32 | 1.378 (4) |
C3—C4 | 1.365 (4) | C31—H31A | 0.9300 |
C3—H3A | 0.9300 | C32—C33 | 1.378 (4) |
C4—C5 | 1.383 (4) | C32—H32A | 0.9300 |
C4—H4A | 0.9300 | C33—C34 | 1.396 (3) |
C5—C6 | 1.378 (3) | C33—H33A | 0.9300 |
C5—H5A | 0.9300 | C34—C35 | 1.495 (3) |
C7—C9 | 1.489 (4) | C35—C36 | 1.495 (3) |
C7—C8 | 1.502 (3) | C36—H36A | 0.9600 |
C8—H8A | 0.9600 | C36—H36B | 0.9600 |
C8—H8B | 0.9600 | C36—H36C | 0.9600 |
C8—H8C | 0.9600 | C37—C38 | 1.375 (3) |
C9—C10 | 1.385 (3) | C37—C42 | 1.376 (3) |
C10—C11 | 1.359 (4) | C38—C39 | 1.377 (4) |
C10—H10A | 0.9300 | C38—H38A | 0.9300 |
C11—C12 | 1.384 (4) | C39—C40 | 1.358 (4) |
C11—H11A | 0.9300 | C39—H39A | 0.9300 |
C12—C13 | 1.383 (3) | C40—C41 | 1.374 (4) |
C12—H12A | 0.9300 | C40—H40A | 0.9300 |
C13—C14 | 1.501 (3) | C41—C42 | 1.383 (4) |
C14—C15 | 1.490 (3) | C41—H41A | 0.9300 |
C15—H15A | 0.9600 | C42—H42A | 0.9300 |
C15—H15B | 0.9600 | Cl6—C43 | 1.750 (4) |
C15—H15C | 0.9600 | Cl5—C43 | 1.748 (4) |
C16—C17 | 1.373 (3) | C43—H43A | 0.9700 |
C16—C21 | 1.378 (4) | C43—H43B | 0.9700 |
N2—Mn1—N3 | 71.44 (7) | C21—C16—N3 | 119.5 (2) |
N2—Mn1—N1 | 71.40 (7) | C16—C17—C18 | 119.1 (3) |
N3—Mn1—N1 | 142.81 (7) | C16—C17—H17A | 120.4 |
N2—Mn1—Cl2 | 118.40 (5) | C18—C17—H17A | 120.4 |
N3—Mn1—Cl2 | 100.02 (5) | C19—C18—C17 | 120.9 (3) |
N1—Mn1—Cl2 | 98.81 (6) | C19—C18—H18A | 119.5 |
N2—Mn1—Cl1 | 123.33 (5) | C17—C18—H18A | 119.5 |
N3—Mn1—Cl1 | 98.45 (6) | C20—C19—C18 | 119.7 (3) |
N1—Mn1—Cl1 | 100.39 (6) | C20—C19—H19A | 120.1 |
Cl2—Mn1—Cl1 | 118.26 (3) | C18—C19—H19A | 120.1 |
N5—Mn2—N4 | 71.49 (7) | C19—C20—C21 | 120.4 (3) |
N5—Mn2—N6 | 70.90 (7) | C19—C20—H20A | 119.8 |
N4—Mn2—N6 | 142.25 (7) | C21—C20—H20A | 119.8 |
N5—Mn2—Cl4 | 125.72 (5) | C16—C21—C20 | 119.8 (3) |
N4—Mn2—Cl4 | 103.15 (6) | C16—C21—H21A | 120.1 |
N6—Mn2—Cl4 | 101.10 (6) | C20—C21—H21A | 120.1 |
N5—Mn2—Cl3 | 117.98 (5) | C27—C22—C23 | 120.4 (3) |
N4—Mn2—Cl3 | 98.18 (6) | C27—C22—H22A | 119.8 |
N6—Mn2—Cl3 | 96.48 (5) | C23—C22—H22A | 119.8 |
Cl4—Mn2—Cl3 | 116.25 (3) | C24—C23—C22 | 120.5 (3) |
C7—N1—C6 | 120.6 (2) | C24—C23—H23A | 119.8 |
C7—N1—Mn1 | 117.35 (16) | C22—C23—H23A | 119.8 |
C6—N1—Mn1 | 122.06 (14) | C23—C24—C25 | 119.7 (3) |
C13—N2—C9 | 120.1 (2) | C23—C24—H24A | 120.1 |
C13—N2—Mn1 | 119.96 (15) | C25—C24—H24A | 120.1 |
C9—N2—Mn1 | 119.85 (16) | C24—C25—C26 | 121.2 (3) |
C14—N3—C16 | 121.0 (2) | C24—C25—H25A | 119.4 |
C14—N3—Mn1 | 117.94 (15) | C26—C25—H25A | 119.4 |
C16—N3—Mn1 | 121.07 (14) | C27—C26—C25 | 118.4 (3) |
C28—N4—C27 | 120.8 (2) | C27—C26—H26A | 120.8 |
C28—N4—Mn2 | 118.48 (16) | C25—C26—H26A | 120.8 |
C27—N4—Mn2 | 120.73 (15) | C22—C27—C26 | 119.8 (3) |
C34—N5—C30 | 120.3 (2) | C22—C27—N4 | 120.6 (2) |
C34—N5—Mn2 | 120.13 (15) | C26—C27—N4 | 119.5 (2) |
C30—N5—Mn2 | 119.46 (15) | N4—C28—C29 | 125.5 (2) |
C35—N6—C37 | 122.1 (2) | N4—C28—C30 | 115.9 (2) |
C35—N6—Mn2 | 119.02 (16) | C29—C28—C30 | 118.6 (2) |
C37—N6—Mn2 | 118.89 (14) | C28—C29—H29A | 109.5 |
C2—C1—C6 | 120.0 (2) | C28—C29—H29B | 109.5 |
C2—C1—H1A | 120.0 | H29A—C29—H29B | 109.5 |
C6—C1—H1A | 120.0 | C28—C29—H29C | 109.5 |
C3—C2—C1 | 120.3 (3) | H29A—C29—H29C | 109.5 |
C3—C2—H2A | 119.9 | H29B—C29—H29C | 109.5 |
C1—C2—H2A | 119.9 | N5—C30—C31 | 121.4 (2) |
C2—C3—C4 | 120.1 (3) | N5—C30—C28 | 114.6 (2) |
C2—C3—H3A | 119.9 | C31—C30—C28 | 123.9 (2) |
C4—C3—H3A | 119.9 | C32—C31—C30 | 118.9 (2) |
C3—C4—C5 | 120.4 (3) | C32—C31—H31A | 120.5 |
C3—C4—H4A | 119.8 | C30—C31—H31A | 120.5 |
C5—C4—H4A | 119.8 | C33—C32—C31 | 119.5 (2) |
C6—C5—C4 | 119.8 (3) | C33—C32—H32A | 120.3 |
C6—C5—H5A | 120.1 | C31—C32—H32A | 120.3 |
C4—C5—H5A | 120.1 | C32—C33—C34 | 118.7 (2) |
C5—C6—C1 | 119.3 (2) | C32—C33—H33A | 120.6 |
C5—C6—N1 | 121.4 (2) | C34—C33—H33A | 120.6 |
C1—C6—N1 | 119.3 (2) | N5—C34—C33 | 121.2 (2) |
N1—C7—C9 | 116.1 (2) | N5—C34—C35 | 114.5 (2) |
N1—C7—C8 | 126.4 (2) | C33—C34—C35 | 124.2 (2) |
C9—C7—C8 | 117.5 (2) | N6—C35—C34 | 115.4 (2) |
C7—C8—H8A | 109.5 | N6—C35—C36 | 125.2 (2) |
C7—C8—H8B | 109.5 | C34—C35—C36 | 119.4 (2) |
H8A—C8—H8B | 109.5 | C35—C36—H36A | 109.5 |
C7—C8—H8C | 109.5 | C35—C36—H36B | 109.5 |
H8A—C8—H8C | 109.5 | H36A—C36—H36B | 109.5 |
H8B—C8—H8C | 109.5 | C35—C36—H36C | 109.5 |
N2—C9—C10 | 120.9 (2) | H36A—C36—H36C | 109.5 |
N2—C9—C7 | 115.2 (2) | H36B—C36—H36C | 109.5 |
C10—C9—C7 | 123.9 (2) | C38—C37—C42 | 119.9 (2) |
C11—C10—C9 | 119.2 (2) | C38—C37—N6 | 119.8 (2) |
C11—C10—H10A | 120.4 | C42—C37—N6 | 120.0 (2) |
C9—C10—H10A | 120.4 | C37—C38—C39 | 120.4 (3) |
C10—C11—C12 | 120.0 (2) | C37—C38—H38A | 119.8 |
C10—C11—H11A | 120.0 | C39—C38—H38A | 119.8 |
C12—C11—H11A | 120.0 | C40—C39—C38 | 120.2 (3) |
C13—C12—C11 | 118.5 (3) | C40—C39—H39A | 119.9 |
C13—C12—H12A | 120.7 | C38—C39—H39A | 119.9 |
C11—C12—H12A | 120.7 | C39—C40—C41 | 119.7 (3) |
N2—C13—C12 | 121.2 (2) | C39—C40—H40A | 120.1 |
N2—C13—C14 | 114.5 (2) | C41—C40—H40A | 120.1 |
C12—C13—C14 | 124.3 (2) | C40—C41—C42 | 120.9 (3) |
N3—C14—C15 | 125.5 (2) | C40—C41—H41A | 119.5 |
N3—C14—C13 | 116.0 (2) | C42—C41—H41A | 119.5 |
C15—C14—C13 | 118.6 (2) | C37—C42—C41 | 118.9 (3) |
C14—C15—H15A | 109.5 | C37—C42—H42A | 120.6 |
C14—C15—H15B | 109.5 | C41—C42—H42A | 120.6 |
H15A—C15—H15B | 109.5 | Cl5—C43—Cl6 | 111.9 (2) |
C14—C15—H15C | 109.5 | Cl5—C43—H43A | 109.2 |
H15A—C15—H15C | 109.5 | Cl6—C43—H43A | 109.2 |
H15B—C15—H15C | 109.5 | Cl5—C43—H43B | 109.2 |
C17—C16—C21 | 120.0 (2) | Cl6—C43—H43B | 109.2 |
C17—C16—N3 | 120.4 (2) | H43A—C43—H43B | 107.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Cl3i | 0.93 | 2.77 | 3.668 (3) | 163 |
C10—H10A···Cl3 | 0.93 | 2.79 | 3.675 (3) | 160 |
C43—H43B···Cl3 | 0.97 | 2.66 | 3.587 (4) | 161 |
C15—H15B···Cl2ii | 0.96 | 2.78 | 3.592 (3) | 142 |
C31—H31A···Cl2iii | 0.93 | 2.73 | 3.629 (3) | 164 |
C29—H29C···Cl1iii | 0.96 | 2.75 | 3.676 (3) | 162 |
C36—H36C···Cl1iv | 0.96 | 2.81 | 3.473 (3) | 127 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z; (iii) x+1, y−1, z; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [MnCl2(C21H19N3)]·0.5CH2Cl2 |
Mr | 481.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 9.007 (2), 12.834 (3), 20.139 (5) |
α, β, γ (°) | 79.582 (16), 79.230 (16), 86.698 (16) |
V (Å3) | 2248.6 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.42 × 0.38 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.678, 0.808 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25241, 11765, 7352 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.687 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.121, 1.00 |
No. of reflections | 11765 |
No. of parameters | 518 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.51 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Mn1—N2 | 2.1856 (19) | Mn2—N5 | 2.2001 (19) |
Mn1—N3 | 2.291 (2) | Mn2—N4 | 2.265 (2) |
Mn1—N1 | 2.3084 (19) | Mn2—N6 | 2.274 (2) |
Mn1—Cl2 | 2.3244 (8) | Mn2—Cl4 | 2.3174 (9) |
Mn1—Cl1 | 2.3279 (9) | Mn2—Cl3 | 2.3426 (8) |
N2—Mn1—N3 | 71.44 (7) | N5—Mn2—N4 | 71.49 (7) |
N2—Mn1—N1 | 71.40 (7) | N5—Mn2—N6 | 70.90 (7) |
N3—Mn1—N1 | 142.81 (7) | N4—Mn2—N6 | 142.25 (7) |
N2—Mn1—Cl2 | 118.40 (5) | N5—Mn2—Cl4 | 125.72 (5) |
N3—Mn1—Cl2 | 100.02 (5) | N4—Mn2—Cl4 | 103.15 (6) |
N1—Mn1—Cl2 | 98.81 (6) | N6—Mn2—Cl4 | 101.10 (6) |
N2—Mn1—Cl1 | 123.33 (5) | N5—Mn2—Cl3 | 117.98 (5) |
N3—Mn1—Cl1 | 98.45 (6) | N4—Mn2—Cl3 | 98.18 (6) |
N1—Mn1—Cl1 | 100.39 (6) | N6—Mn2—Cl3 | 96.48 (5) |
Cl2—Mn1—Cl1 | 118.26 (3) | Cl4—Mn2—Cl3 | 116.25 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Cl3i | 0.93 | 2.77 | 3.668 (3) | 163 |
C10—H10A···Cl3 | 0.93 | 2.79 | 3.675 (3) | 160 |
C43—H43B···Cl3 | 0.97 | 2.66 | 3.587 (4) | 161 |
C15—H15B···Cl2ii | 0.96 | 2.78 | 3.592 (3) | 142 |
C31—H31A···Cl2iii | 0.93 | 2.73 | 3.629 (3) | 164 |
C29—H29C···Cl1iii | 0.96 | 2.75 | 3.676 (3) | 162 |
C36—H36C···Cl1iv | 0.96 | 2.81 | 3.473 (3) | 127 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z; (iii) x+1, y−1, z; (iv) x, y−1, z. |
C—H···Cga | H···Cg | C···Cg | γb | C—H···Cg) |
C11—H11A···Cg(C22→C27) | 2.85 | 3.604 (3) | 10.09 | 139 |
C32—H32A···Cg(N2→C13)i | 2.93 | 3.473 (3) | 6.10 | 119 |
C32—H32A···Cg(C1→C6)ii | 2.98 | 3.620 (3) | 12.23 | 127 |
Notes: Cga = centroid of the six-membered ring. γb = angle defined by a line connecting the centroid of the six-membered ring with H atom and the normal to the six-membered ring. Symmetry codes: (i) x,-1+y,z; (ii) 1+x,-1+y,z. |
π···π contacts | Cg···Cg | αa | βb | Cg···Plane |
Cg(C22A→C27A)···Cg(C22B→C27B) | 5.195 (2) | 0.00 | 47.30 | 3.523 |
Notes: αa = angle between the planes of the two aromatic rings. βb = angle between Cg···Cg line and normal to the plane of the first aromatic ring. |
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In recent years, many researchers focused on metal complexes based on Schiff base ligands derived from 2,6-diacetylpyridine due to their antimicrobial, cytotoxic, antioxidant, especially their catalytic activities (Reardon et al., 2002; Esteruelas et al., 2003; Pradhan et al.. 2003; Gibson et al.. 2001). The related metal complexes were synthesized from the condensation of 2,6-diacetylpyridine and aniline and were reported last several years (Marganian et al., 1995; Mentes et al., 2001; Trivedi et al.. 2007; Jiang et al.. 2005). Here, we report on the synthesis and crystal structure of analogous Mn(II) complex, (I). The title compound, (I), (Fig. 1) is isostructural with the the analogous nickel(II) complex (Fan et al., 2005). Each Mn(II) atom is coordinated by three N atoms (pyridyl N and two imino N atoms) from Plep Schiff base and two Cl anions, disposed in a distorted trigonal-bipyramid geometry as suggest the bond lengths and three trans angles at Mn(II) (Table 1). The pyridyl N atom and two Cl anions are disposed in the equatorial plane and the aptical position is occupied by two imino N atoms. In each Mn(Plep)Cl2 molecule, the Mn—N(pyridyl) bond is significantly shorter than the Mn—N(imino) bond, with the formal double bond character of the imino bonds N3—C14, N1—C7, N4—C28 and N6—C35 [C=N distances in the range 1.273 (3) to 1.280 (3) Å]. Each of two Mn(II) atoms is coplanar with the N3-ligand plane with the deviations from the plane by 0.0149 Å and 0.0289 Å, respectively. The molecules are held together by intermolecular hydrogen bond C—H···Cl (Table 2a), CH···π (Table 2 b), and p\- pιnteractions (Table 2c) forming a three-dimensional network (Fig. 2). The phenyl ring C4 and pyridyl ring C10 donate H atoms to Cl3 to form C—H···Cli and C—H···Clii hydrogen bonds, respectively [symmetry codes i = -1 + x, y, z; ii = x, y, z]. The Cl3 also accepts H atom from solvent dichloromethane C43 to form C—H···Clii hydrogen bond. Similarly, Cl2 accepts H atoms from C15 and C31 to form C—H···Cliii and C—H···CliV hydrogen bonds [symmetry codes iii = 1 - x, 2 - y, -z; iv = 1 + x, -1 + y, z]. In addition, methyl C29 and C36 atoms donate H atoms to Cl1 to form C—H···Cliv and C—H···Clv hydrogen bonds [symmetry codes v = x, -1 + y, z] (Table 2a, Fig. 2). In addition, the CH···π interaction between methyl group C8 and C11 of the aromatic ring, and p\- pιnteractions between the aromatic rings C22→C27 and C37→ C42 of the Plep (Table 2c, Fig. 2) are pronounced in this crystal structure. To classify these interactions the numerical criteria given in the literature were used (Štefanić et al., 2006; Nishio et al., 2004).