Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058783/rk2061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058783/rk2061Isup2.hkl |
CCDC reference: 672729
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.005 Å
- R factor = 0.052
- wR factor = 0.129
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1D ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Calderazzo et al. (2003); Gross et al. (2000); Liao et al. (2000); Meng et al. (2006a,b); Xu et al. (2003); Yu et al. (2006).
All reagents and solvents were used as obtained without further purification. Compound I was synthesized by refluxing stoichiometric quantities (1:1 molar ratio) of IDB (0.28 g, 1.0 mmol) and manganese(II) chloride tetrahydrate (0.20 g, 1 mmol) in methanol (20 ml) at 333 K for 2 h. The solution was cooled to room temperature, filtered and evaporated to obtain the product (yield 40%). Block colourless crystals of I suitable for X-ray single-crystal diffraction were grown by slow evaporation of the methanol solution.
H atoms bonded to carbon atoms were located at the geometrical positions with C–H = 0.93Å (aromatic), 0.97Å (methylene) and 0.96Å (methyl); Uĩso~(H) = 1.2U~eq~(aromatic and methylene C) and 1.5Ueq(methyl C). All the other H atoms were located from the difference maps with the constraints of Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O) and the N (or O)–H distances were refined freely. Cg1 is the centroid defined by phenyl atoms C11/C16.
Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
[MnCl2(C16H15N5)(CH4O)] | F(000) = 892 |
Mr = 435.21 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 752 reflections |
a = 7.2064 (6) Å | θ = 2.6–21.0° |
b = 13.8208 (11) Å | µ = 0.99 mm−1 |
c = 19.3825 (15) Å | T = 297 K |
β = 100.608 (2)° | Block, colorless |
V = 1897.5 (3) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4112 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2639 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
0.3° wide ω–scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; (Sheldrick, 2001) | h = −9→9 |
Tmin = 0.826, Tmax = 0.907 | k = −17→17 |
14752 measured reflections | l = −23→24 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0669P)2] where P = (Fo2 + 2Fc2)/3 |
4112 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
[MnCl2(C16H15N5)(CH4O)] | V = 1897.5 (3) Å3 |
Mr = 435.21 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2064 (6) Å | µ = 0.99 mm−1 |
b = 13.8208 (11) Å | T = 297 K |
c = 19.3825 (15) Å | 0.20 × 0.10 × 0.10 mm |
β = 100.608 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 4112 independent reflections |
Absorption correction: multi-scan (SADABS; (Sheldrick, 2001) | 2639 reflections with I > 2σ(I) |
Tmin = 0.826, Tmax = 0.907 | Rint = 0.068 |
14752 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.52 e Å−3 |
4112 reflections | Δρmin = −0.35 e Å−3 |
248 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 > 2σ(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 | 0.91501 (7) | 0.48326 (3) | 0.21677 (3) | 0.03220 (17) | |
C1 | 0.8660 (5) | 0.6318 (2) | 0.08502 (18) | 0.0388 (8) | |
H1A | 0.9896 | 0.6395 | 0.0726 | 0.047* | |
H1B | 0.7838 | 0.6819 | 0.0612 | 0.047* | |
C2 | 0.7881 (5) | 0.5346 (2) | 0.06223 (17) | 0.0342 (8) | |
C3 | 0.6897 (5) | 0.4104 (2) | −0.00642 (17) | 0.0350 (8) | |
C4 | 0.6300 (5) | 0.3455 (3) | −0.06046 (19) | 0.0431 (9) | |
H4 | 0.6173 | 0.3638 | −0.1073 | 0.052* | |
C5 | 0.5906 (5) | 0.2535 (3) | −0.0419 (2) | 0.0479 (10) | |
H5 | 0.5513 | 0.2080 | −0.0769 | 0.058* | |
C6 | 0.6082 (5) | 0.2261 (3) | 0.0288 (2) | 0.0476 (10) | |
H6 | 0.5803 | 0.1628 | 0.0396 | 0.057* | |
C7 | 0.6658 (5) | 0.2910 (3) | 0.08260 (19) | 0.0433 (9) | |
H7 | 0.6758 | 0.2729 | 0.1294 | 0.052* | |
C8 | 0.7082 (5) | 0.3840 (2) | 0.06417 (17) | 0.0338 (8) | |
C9 | 1.0263 (6) | 0.7083 (3) | 0.19505 (18) | 0.0469 (10) | |
H9A | 0.9746 | 0.7732 | 0.1950 | 0.056* | |
H9B | 1.1301 | 0.7096 | 0.1696 | 0.056* | |
C10 | 1.0954 (5) | 0.6761 (2) | 0.26850 (17) | 0.0372 (8) | |
C11 | 1.2508 (5) | 0.6760 (2) | 0.37731 (19) | 0.0392 (9) | |
C12 | 1.3639 (6) | 0.6942 (3) | 0.4423 (2) | 0.0540 (11) | |
H12 | 1.4338 | 0.7509 | 0.4511 | 0.065* | |
C13 | 1.3668 (6) | 0.6248 (3) | 0.4922 (2) | 0.0564 (11) | |
H13 | 1.4383 | 0.6353 | 0.5366 | 0.068* | |
C14 | 1.2677 (6) | 0.5393 (3) | 0.4793 (2) | 0.0557 (11) | |
H14 | 1.2742 | 0.4939 | 0.5151 | 0.067* | |
C15 | 1.1584 (6) | 0.5197 (3) | 0.4140 (2) | 0.0461 (9) | |
H15 | 1.0923 | 0.4619 | 0.4052 | 0.055* | |
C16 | 1.1519 (5) | 0.5898 (2) | 0.36275 (18) | 0.0368 (8) | |
C17 | 0.6031 (7) | 0.5393 (5) | 0.3127 (3) | 0.0925 (18) | |
H17A | 0.7198 | 0.5321 | 0.3454 | 0.139* | |
H17B | 0.5121 | 0.4941 | 0.3241 | 0.139* | |
H17C | 0.5565 | 0.6040 | 0.3153 | 0.139* | |
Cl1 | 1.22979 (12) | 0.45919 (6) | 0.16820 (5) | 0.0397 (2) | |
Cl2 | 0.92642 (16) | 0.32687 (7) | 0.27362 (5) | 0.0570 (3) | |
N1 | 0.8810 (4) | 0.6417 (2) | 0.16111 (15) | 0.0381 (7) | |
H1D | 0.779 (3) | 0.660 (3) | 0.1722 (18) | 0.046* | |
N2 | 0.7420 (4) | 0.5069 (2) | −0.00540 (15) | 0.0390 (7) | |
H2A | 0.753 (5) | 0.543 (2) | −0.0413 (14) | 0.047* | |
N3 | 0.7698 (4) | 0.46425 (19) | 0.10614 (14) | 0.0341 (7) | |
N4 | 1.2130 (4) | 0.7290 (2) | 0.31645 (17) | 0.0445 (8) | |
H4A | 1.238 (5) | 0.7869 (15) | 0.3082 (18) | 0.053* | |
N5 | 1.0545 (4) | 0.59134 (19) | 0.29307 (14) | 0.0344 (7) | |
O1 | 0.6339 (4) | 0.5209 (2) | 0.24405 (15) | 0.0537 (8) | |
H1C | 0.538 (7) | 0.498 (3) | 0.222 (3) | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0362 (3) | 0.0311 (3) | 0.0296 (3) | −0.0019 (2) | 0.0069 (2) | 0.0009 (2) |
C1 | 0.037 (2) | 0.039 (2) | 0.041 (2) | 0.0014 (16) | 0.0091 (16) | 0.0113 (16) |
C2 | 0.032 (2) | 0.039 (2) | 0.0318 (19) | 0.0018 (15) | 0.0055 (15) | 0.0052 (15) |
C3 | 0.0258 (19) | 0.047 (2) | 0.0329 (19) | 0.0029 (15) | 0.0074 (15) | −0.0024 (16) |
C4 | 0.040 (2) | 0.055 (2) | 0.036 (2) | 0.0002 (18) | 0.0122 (17) | −0.0039 (17) |
C5 | 0.046 (2) | 0.054 (2) | 0.045 (2) | −0.0026 (19) | 0.0109 (18) | −0.0135 (19) |
C6 | 0.044 (2) | 0.043 (2) | 0.057 (3) | −0.0089 (18) | 0.0147 (19) | −0.0004 (19) |
C7 | 0.045 (2) | 0.048 (2) | 0.038 (2) | −0.0049 (18) | 0.0123 (17) | 0.0033 (17) |
C8 | 0.0249 (18) | 0.044 (2) | 0.0323 (18) | −0.0026 (15) | 0.0045 (14) | 0.0004 (15) |
C9 | 0.062 (3) | 0.035 (2) | 0.046 (2) | −0.0116 (18) | 0.015 (2) | 0.0004 (17) |
C10 | 0.044 (2) | 0.034 (2) | 0.036 (2) | −0.0037 (15) | 0.0146 (17) | −0.0064 (15) |
C11 | 0.035 (2) | 0.039 (2) | 0.044 (2) | −0.0013 (16) | 0.0108 (17) | −0.0080 (17) |
C12 | 0.045 (3) | 0.058 (3) | 0.058 (3) | −0.007 (2) | 0.005 (2) | −0.021 (2) |
C13 | 0.053 (3) | 0.058 (3) | 0.052 (3) | 0.007 (2) | −0.007 (2) | −0.011 (2) |
C14 | 0.061 (3) | 0.058 (3) | 0.047 (2) | 0.012 (2) | 0.004 (2) | 0.004 (2) |
C15 | 0.050 (2) | 0.039 (2) | 0.049 (2) | 0.0008 (18) | 0.0064 (19) | −0.0021 (18) |
C16 | 0.036 (2) | 0.038 (2) | 0.038 (2) | 0.0001 (15) | 0.0099 (16) | −0.0084 (16) |
C17 | 0.066 (3) | 0.147 (5) | 0.072 (3) | −0.011 (3) | 0.033 (3) | −0.042 (3) |
Cl1 | 0.0371 (5) | 0.0421 (5) | 0.0412 (5) | 0.0014 (4) | 0.0109 (4) | 0.0014 (4) |
Cl2 | 0.0804 (8) | 0.0424 (6) | 0.0490 (6) | −0.0045 (5) | 0.0138 (5) | 0.0134 (4) |
N1 | 0.0419 (19) | 0.0393 (17) | 0.0360 (17) | −0.0008 (14) | 0.0150 (14) | −0.0014 (13) |
N2 | 0.0452 (19) | 0.0418 (18) | 0.0307 (17) | 0.0015 (14) | 0.0088 (14) | 0.0059 (13) |
N3 | 0.0335 (17) | 0.0389 (16) | 0.0287 (15) | 0.0015 (12) | 0.0026 (12) | 0.0006 (12) |
N4 | 0.052 (2) | 0.0340 (17) | 0.050 (2) | −0.0144 (15) | 0.0159 (16) | −0.0113 (15) |
N5 | 0.0339 (17) | 0.0329 (16) | 0.0373 (16) | −0.0025 (12) | 0.0087 (13) | −0.0051 (12) |
O1 | 0.0311 (15) | 0.077 (2) | 0.0546 (18) | −0.0044 (14) | 0.0127 (13) | −0.0170 (15) |
Mn1—N5 | 2.209 (3) | C9—C10 | 1.487 (5) |
Mn1—N3 | 2.222 (3) | C9—H9A | 0.9700 |
Mn1—O1 | 2.247 (3) | C9—H9B | 0.9700 |
Mn1—Cl2 | 2.4207 (10) | C10—N5 | 1.318 (4) |
Mn1—N1 | 2.434 (3) | C10—N4 | 1.351 (4) |
Mn1—Cl1 | 2.6322 (10) | C11—N4 | 1.373 (5) |
C1—N1 | 1.465 (4) | C11—C16 | 1.390 (5) |
C1—C2 | 1.492 (5) | C11—C12 | 1.391 (5) |
C1—H1A | 0.9700 | C12—C13 | 1.361 (6) |
C1—H1B | 0.9700 | C12—H12 | 0.9300 |
C2—N3 | 1.314 (4) | C13—C14 | 1.379 (6) |
C2—N2 | 1.347 (4) | C13—H13 | 0.9300 |
C3—N2 | 1.385 (4) | C14—C15 | 1.389 (5) |
C3—C4 | 1.386 (5) | C14—H14 | 0.9300 |
C3—C8 | 1.399 (4) | C15—C16 | 1.383 (5) |
C4—C5 | 1.365 (5) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—N5 | 1.403 (4) |
C5—C6 | 1.405 (5) | C17—O1 | 1.412 (5) |
C5—H5 | 0.9300 | C17—H17A | 0.9600 |
C6—C7 | 1.380 (5) | C17—H17B | 0.9600 |
C6—H6 | 0.9300 | C17—H17C | 0.9600 |
C7—C8 | 1.383 (5) | N1—H1D | 0.839 (18) |
C7—H7 | 0.9300 | N2—H2A | 0.871 (18) |
C8—N3 | 1.399 (4) | N4—H4A | 0.842 (18) |
C9—N1 | 1.457 (4) | O1—H1C | 0.80 (5) |
N5—Mn1—N3 | 143.27 (10) | N5—C10—N4 | 112.7 (3) |
N5—Mn1—O1 | 90.26 (10) | N5—C10—C9 | 123.7 (3) |
N3—Mn1—O1 | 88.26 (10) | N4—C10—C9 | 123.6 (3) |
N5—Mn1—Cl2 | 109.02 (8) | N4—C11—C16 | 105.6 (3) |
N3—Mn1—Cl2 | 107.71 (8) | N4—C11—C12 | 132.2 (3) |
O1—Mn1—Cl2 | 93.23 (8) | C16—C11—C12 | 122.2 (4) |
N5—Mn1—N1 | 71.61 (10) | C13—C12—C11 | 116.5 (4) |
N3—Mn1—N1 | 71.79 (10) | C13—C12—H12 | 121.8 |
O1—Mn1—N1 | 82.78 (10) | C11—C12—H12 | 121.8 |
Cl2—Mn1—N1 | 175.97 (8) | C12—C13—C14 | 122.4 (4) |
N5—Mn1—Cl1 | 90.52 (7) | C12—C13—H13 | 118.8 |
N3—Mn1—Cl1 | 85.63 (8) | C14—C13—H13 | 118.8 |
O1—Mn1—Cl1 | 170.78 (8) | C13—C14—C15 | 121.3 (4) |
Cl2—Mn1—Cl1 | 95.20 (4) | C13—C14—H14 | 119.3 |
N1—Mn1—Cl1 | 88.75 (7) | C15—C14—H14 | 119.3 |
N1—C1—C2 | 109.6 (3) | C16—C15—C14 | 117.2 (4) |
N1—C1—H1A | 109.7 | C16—C15—H15 | 121.4 |
C2—C1—H1A | 109.7 | C14—C15—H15 | 121.4 |
N1—C1—H1B | 109.7 | C15—C16—C11 | 120.4 (3) |
C2—C1—H1B | 109.7 | C15—C16—N5 | 130.3 (3) |
H1A—C1—H1B | 108.2 | C11—C16—N5 | 109.3 (3) |
N3—C2—N2 | 112.5 (3) | O1—C17—H17A | 109.5 |
N3—C2—C1 | 123.5 (3) | O1—C17—H17B | 109.5 |
N2—C2—C1 | 123.8 (3) | H17A—C17—H17B | 109.5 |
N2—C3—C4 | 132.8 (3) | O1—C17—H17C | 109.5 |
N2—C3—C8 | 105.1 (3) | H17A—C17—H17C | 109.5 |
C4—C3—C8 | 122.1 (3) | H17B—C17—H17C | 109.5 |
C5—C4—C3 | 117.0 (3) | C9—N1—C1 | 115.3 (3) |
C5—C4—H4 | 121.5 | C9—N1—Mn1 | 111.3 (2) |
C3—C4—H4 | 121.5 | C1—N1—Mn1 | 110.2 (2) |
C4—C5—C6 | 121.5 (4) | C9—N1—H1D | 107 (3) |
C4—C5—H5 | 119.3 | C1—N1—H1D | 112 (3) |
C6—C5—H5 | 119.3 | Mn1—N1—H1D | 100 (3) |
C7—C6—C5 | 121.5 (4) | C2—N2—C3 | 107.8 (3) |
C7—C6—H6 | 119.2 | C2—N2—H2A | 125 (2) |
C5—C6—H6 | 119.2 | C3—N2—H2A | 127 (2) |
C6—C7—C8 | 117.3 (3) | C2—N3—C8 | 105.6 (3) |
C6—C7—H7 | 121.4 | C2—N3—Mn1 | 116.9 (2) |
C8—C7—H7 | 121.4 | C8—N3—Mn1 | 134.2 (2) |
C7—C8—C3 | 120.6 (3) | C10—N4—C11 | 107.6 (3) |
C7—C8—N3 | 130.4 (3) | C10—N4—H4A | 121 (2) |
C3—C8—N3 | 108.9 (3) | C11—N4—H4A | 131 (2) |
N1—C9—C10 | 109.2 (3) | C10—N5—C16 | 104.8 (3) |
N1—C9—H9A | 109.8 | C10—N5—Mn1 | 117.6 (2) |
C10—C9—H9A | 109.8 | C16—N5—Mn1 | 136.0 (2) |
N1—C9—H9B | 109.8 | C17—O1—Mn1 | 124.6 (3) |
C10—C9—H9B | 109.8 | C17—O1—H1C | 107 (4) |
H9A—C9—H9B | 108.3 | Mn1—O1—H1C | 121 (4) |
N1—C1—C2—N3 | −11.2 (5) | C1—C2—N3—C8 | −175.0 (3) |
N1—C1—C2—N2 | 173.9 (3) | N2—C2—N3—Mn1 | 162.9 (2) |
N2—C3—C4—C5 | 179.5 (4) | C1—C2—N3—Mn1 | −12.5 (4) |
C8—C3—C4—C5 | −0.4 (5) | C7—C8—N3—C2 | −179.7 (4) |
C3—C4—C5—C6 | 0.6 (5) | C3—C8—N3—C2 | −0.4 (4) |
C4—C5—C6—C7 | 0.0 (6) | C7—C8—N3—Mn1 | 22.3 (5) |
C5—C6—C7—C8 | −0.8 (5) | C3—C8—N3—Mn1 | −158.4 (2) |
C6—C7—C8—C3 | 1.0 (5) | N5—Mn1—N3—C2 | 14.7 (3) |
C6—C7—C8—N3 | −179.8 (3) | O1—Mn1—N3—C2 | 102.8 (3) |
N2—C3—C8—C7 | 179.7 (3) | Cl2—Mn1—N3—C2 | −164.4 (2) |
C4—C3—C8—C7 | −0.4 (5) | N1—Mn1—N3—C2 | 19.8 (2) |
N2—C3—C8—N3 | 0.3 (4) | Cl1—Mn1—N3—C2 | −70.3 (2) |
C4—C3—C8—N3 | −179.8 (3) | N5—Mn1—N3—C8 | 170.7 (3) |
N1—C9—C10—N5 | 11.3 (5) | O1—Mn1—N3—C8 | −101.2 (3) |
N1—C9—C10—N4 | −171.4 (3) | Cl2—Mn1—N3—C8 | −8.3 (3) |
N4—C11—C12—C13 | 179.2 (4) | N1—Mn1—N3—C8 | 175.9 (3) |
C16—C11—C12—C13 | −2.7 (6) | Cl1—Mn1—N3—C8 | 85.7 (3) |
C11—C12—C13—C14 | 1.7 (6) | N5—C10—N4—C11 | −0.7 (4) |
C12—C13—C14—C15 | −0.1 (7) | C9—C10—N4—C11 | −178.3 (3) |
C13—C14—C15—C16 | −0.6 (6) | C16—C11—N4—C10 | 0.5 (4) |
C14—C15—C16—C11 | −0.4 (5) | C12—C11—N4—C10 | 178.9 (4) |
C14—C15—C16—N5 | −179.5 (4) | N4—C10—N5—C16 | 0.7 (4) |
N4—C11—C16—C15 | −179.3 (3) | C9—C10—N5—C16 | 178.2 (3) |
C12—C11—C16—C15 | 2.1 (5) | N4—C10—N5—Mn1 | −167.3 (2) |
N4—C11—C16—N5 | −0.1 (4) | C9—C10—N5—Mn1 | 10.2 (4) |
C12—C11—C16—N5 | −178.7 (3) | C15—C16—N5—C10 | 178.8 (4) |
C10—C9—N1—C1 | −150.7 (3) | C11—C16—N5—C10 | −0.4 (4) |
C10—C9—N1—Mn1 | −24.3 (4) | C15—C16—N5—Mn1 | −16.6 (6) |
C2—C1—N1—C9 | 153.1 (3) | C11—C16—N5—Mn1 | 164.3 (2) |
C2—C1—N1—Mn1 | 26.1 (3) | N3—Mn1—N5—C10 | −12.2 (3) |
N5—Mn1—N1—C9 | 22.7 (2) | O1—Mn1—N5—C10 | −99.7 (3) |
N3—Mn1—N1—C9 | −154.0 (3) | Cl2—Mn1—N5—C10 | 166.8 (2) |
O1—Mn1—N1—C9 | 115.4 (2) | N1—Mn1—N5—C10 | −17.4 (2) |
Cl1—Mn1—N1—C9 | −68.2 (2) | Cl1—Mn1—N5—C10 | 71.2 (2) |
N5—Mn1—N1—C1 | 151.9 (2) | N3—Mn1—N5—C16 | −175.4 (3) |
N3—Mn1—N1—C1 | −24.8 (2) | O1—Mn1—N5—C16 | 97.2 (3) |
O1—Mn1—N1—C1 | −115.4 (2) | Cl2—Mn1—N5—C16 | 3.7 (3) |
Cl1—Mn1—N1—C1 | 61.0 (2) | N1—Mn1—N5—C16 | 179.5 (3) |
N3—C2—N2—C3 | −0.3 (4) | Cl1—Mn1—N5—C16 | −92.0 (3) |
C1—C2—N2—C3 | 175.1 (3) | N5—Mn1—O1—C17 | −40.7 (4) |
C4—C3—N2—C2 | −180.0 (4) | N3—Mn1—O1—C17 | 176.0 (4) |
C8—C3—N2—C2 | 0.0 (4) | Cl2—Mn1—O1—C17 | 68.4 (4) |
N2—C2—N3—C8 | 0.4 (4) | N1—Mn1—O1—C17 | −112.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···Cl1i | 0.84 (2) | 2.43 (2) | 3.215 (3) | 156 (3) |
N2—H2A···Cl1ii | 0.87 (2) | 2.49 (3) | 3.233 (3) | 144 (3) |
O1—H1C···Cl1iii | 0.80 (5) | 2.34 (5) | 3.129 (3) | 168 (5) |
C6—H6···Cg1iv | 0.93 | 2.75 | 3.354 (5) | 124 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) x−1, y, z; (iv) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [MnCl2(C16H15N5)(CH4O)] |
Mr | 435.21 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 7.2064 (6), 13.8208 (11), 19.3825 (15) |
β (°) | 100.608 (2) |
V (Å3) | 1897.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; (Sheldrick, 2001) |
Tmin, Tmax | 0.826, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14752, 4112, 2639 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.129, 0.95 |
No. of reflections | 4112 |
No. of parameters | 248 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.52, −0.35 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···Cl1i | 0.842 (18) | 2.43 (2) | 3.215 (3) | 156 (3) |
N2—H2A···Cl1ii | 0.871 (18) | 2.49 (3) | 3.233 (3) | 144 (3) |
O1—H1C···Cl1iii | 0.80 (5) | 2.34 (5) | 3.129 (3) | 168 (5) |
C6—H6···Cg1iv | 0.93 | 2.75 | 3.354 (5) | 124 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) x−1, y, z; (iv) −x+3/2, y−1/2, −z+1/2. |
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Di(2-benzimidazolylmethyl)imine (IDB) is a very often used organic N-containing ligand in preparing for metal model complexes aming to mimic the active sites found in natural metalloproteins (Calderazzo et al., 2003; Xu et al., 2003; Gross et al., 2000). In a continuation of our studies on the molecular and supramolecular structure in IDB-containing analogas (Meng et al., 2006a, 2006b; Yu et al., 2006; Liao et al., 2000), now we report the structure of the I.
Compound I have similar unit-cell parameters to the earlier reported ferrous complex (Calderazzo et al., 2003). However, except for the discussion of the metal coordination bond lengths and bond angles in earlier paper, no any description involved with the crystall packing has been given. As expected, the Mn(II) cation in I displays a distorted octahedral coordination geometry which is very simiar to the recently reported analog in which the coordinated ethanol molecule is displaced by methanol here (Yu et al., 2006). Atoms N1/N3/N5/Cl2 from the equatorial plane and the axial positions are occupied by methanol O atom and the Cl1 anion (Fig.1). The Mn—Namine distance is about 0.22Å longer than those between the Mn—Nimine distance. The Mn—Cl bond length involving the axial atom Cl1 is about 0.21Å longer than that involving the equatorial atom Cl2.
In the supramolecular structrue formed by a combination of N(O)···Cl1 hydrogen bonds, C–H···π and π···π interactions, molecules are linked into a three-dimensional network which can be easily analyzed in terms of several substructures listed below.
Firstly, methanol O1 atom in the initial molecule (x, y, z) acting as H-bonding donor, via H1C, to the equatorial Cl1iii atom so forming by tranlation a one-dimensional chain running parallel to the [1 0 0] direction. Similarly, imine N4 atom in the initial molecule acts as H-bonding donor to another Cl1i atom, producing the other one-dimensional chains along the [0 1 0] direction, but this time generated by the 21 axis. These two types of H-bondings suffices linked the molecules I into a two-dimensional network (Fig.2) running parallel to the [0 0 1] direction.
Secondly, the third H-bonding N2–H2A···Cl1ii linked the reference and symmetry related molecules into a centrosymmetric R22(16) ring centered at (1, 1/2, 0). Propagation by inversion of this interaction then generates the simple three-dimensional network (Fig.3).
The crystal packing is stablized by C–H···π and π–π interactions. The initial N2/N3/C2/C3/C8 imidazole ring and N2iv/N3iv/C2iv/C3iv/C8iv have an interplanar spacing of 3.343 (1) Å; the ring-centroid separation is 3.728 (3) Å, corresponding to a ring offset of 1.650 (1) Å. Symmetry codes: (i) 5/2 - x, 1/2 + y, 1/2 - z; (ii) 2 - x,1 - y,-z; (iii) x - 1, y, z; (iv) 1 - x, 1 - y,-z.