Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038421/bi2218sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038421/bi2218Isup2.hkl |
CCDC reference: 660072
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.058
- wR factor = 0.172
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 PLAT793_ALERT_1_G Check the Absolute Configuration of N1 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of N3 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of N4 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (9) 3.28 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn2 (9) 3.30
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
To a solution of Mn(CH3COO)3·2H2O (0.55 g, 2.05 mmol) and 1,4,8,11-tetraazacyclotetradecane (0.40 g, 2.00 mmol) in EtOH (30 ml) were added 20 drops of perchloric acid (60%) and the mixture was stirred for 8 h at room temparature. The resulting precipitate was separated by filtration, washed with EtOH and diethyl ether, then dried to give a yellow powder (0.72 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a MeOH solution.
H atoms on N and C atoms were positioned geometrically and allowed to ride on their respective carrier atoms [N—H = 0.91 Å, C—H = 0.97 or 0.96 Å and Uiso(H) = 1.2Ueq(N or C) or 1.5Ueq(methyl C)]. The H atoms of the water were located from difference maps then allowed to ride on their parent O atom in the final cycles of refinement.
The structure of the title compound contains two chemically equivalent, but crystallographically independent, cationic complexes, both located with their central MnIII atom on a centre of inversion (Fig. 1). In both cations, the MnIII atom is six-coordinated in a distorted octahedral geometry by two O atoms from acetato anions occupying axial positions and four N atoms from 1,4,8,11-tetraazacyclotetradecane (cyclam) occupying equatorial positions (mean lengths: Mn—N 2.036 Å, Mn—O 2.123 Å). The compound displays intra- and intermolecular hydrogen bonding (Fig. 2 & Table 1).
For some related MnIII cyclam complexes, see: Mossin et al. (2005).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXL97.
[Mn(C2H3O2)2(C10H24N4)]ClO4·H2O | F(000) = 1032 |
Mr = 490.83 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2981 reflections |
a = 16.0734 (17) Å | θ = 2.4–24.9° |
b = 8.5147 (9) Å | µ = 0.78 mm−1 |
c = 17.3393 (18) Å | T = 293 K |
β = 113.446 (2)° | Prism, yellow |
V = 2177.1 (4) Å3 | 0.26 × 0.25 × 0.15 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 4452 independent reflections |
Radiation source: fine-focus sealed tube | 3154 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −20→19 |
Tmin = 0.747, Tmax = 0.889 | k = −7→10 |
12476 measured reflections | l = −15→21 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.082P)2 + 1.5997P] where P = (Fo2 + 2Fc2)/3 |
4452 reflections | (Δ/σ)max < 0.001 |
269 parameters | Δρmax = 1.20 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
[Mn(C2H3O2)2(C10H24N4)]ClO4·H2O | V = 2177.1 (4) Å3 |
Mr = 490.83 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.0734 (17) Å | µ = 0.78 mm−1 |
b = 8.5147 (9) Å | T = 293 K |
c = 17.3393 (18) Å | 0.26 × 0.25 × 0.15 mm |
β = 113.446 (2)° |
Bruker SMART 1000 CCD diffractometer | 4452 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3154 reflections with I > 2σ(I) |
Tmin = 0.747, Tmax = 0.889 | Rint = 0.029 |
12476 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.06 | Δρmax = 1.20 e Å−3 |
4452 reflections | Δρmin = −0.66 e Å−3 |
269 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 | 0.0000 | 1.0000 | 0.0000 | 0.0269 (2) | |
O1 | −0.07775 (17) | 0.8393 (3) | 0.03744 (17) | 0.0394 (6) | |
O2 | 0.0207 (2) | 0.6979 (4) | 0.1400 (2) | 0.0601 (9) | |
N1 | 0.0091 (2) | 1.1441 (3) | 0.09685 (19) | 0.0374 (7) | |
H1 | −0.0110 | 1.0882 | 0.1308 | 0.045* | |
N2 | 0.11842 (19) | 0.8864 (4) | 0.06720 (19) | 0.0356 (7) | |
H2 | 0.1057 | 0.8123 | 0.0987 | 0.043* | |
C1 | −0.0573 (3) | 1.2712 (5) | 0.0589 (3) | 0.0525 (12) | |
H1A | −0.0330 | 1.3467 | 0.0315 | 0.063* | |
H1B | −0.0702 | 1.3254 | 0.1021 | 0.063* | |
C2 | 0.1008 (3) | 1.2034 (5) | 0.1507 (3) | 0.0510 (11) | |
H2A | 0.0970 | 1.2659 | 0.1960 | 0.061* | |
H2B | 0.1225 | 1.2709 | 0.1176 | 0.061* | |
C3 | 0.1673 (3) | 1.0717 (6) | 0.1874 (3) | 0.0556 (12) | |
H3A | 0.1418 | 0.9987 | 0.2150 | 0.067* | |
H3B | 0.2222 | 1.1149 | 0.2301 | 0.067* | |
C4 | 0.1927 (3) | 0.9818 (5) | 0.1251 (3) | 0.0533 (12) | |
H4A | 0.2120 | 1.0556 | 0.0928 | 0.064* | |
H4B | 0.2438 | 0.9139 | 0.1555 | 0.064* | |
C5 | 0.1431 (3) | 0.8011 (5) | 0.0045 (3) | 0.0499 (11) | |
H5A | 0.1874 | 0.7199 | 0.0320 | 0.060* | |
H5B | 0.1691 | 0.8731 | −0.0232 | 0.060* | |
C6 | −0.0578 (3) | 0.7385 (4) | 0.0952 (3) | 0.0364 (9) | |
C7 | −0.1366 (3) | 0.6656 (5) | 0.1080 (3) | 0.0509 (11) | |
H7A | −0.1144 | 0.5987 | 0.1566 | 0.076* | |
H7B | −0.1719 | 0.6046 | 0.0594 | 0.076* | |
H7C | −0.1737 | 0.7468 | 0.1162 | 0.076* | |
Mn2 | 0.5000 | 0.0000 | 0.0000 | 0.0314 (2) | |
O3 | 0.39455 (17) | −0.1607 (3) | −0.06614 (18) | 0.0443 (7) | |
O4 | 0.26686 (18) | −0.0244 (3) | −0.1028 (2) | 0.0506 (8) | |
N3 | 0.4109 (2) | 0.1552 (4) | 0.0126 (2) | 0.0403 (8) | |
H3 | 0.3546 | 0.1194 | −0.0207 | 0.048* | |
N4 | 0.5073 (2) | −0.0929 (4) | 0.1113 (2) | 0.0420 (8) | |
H4 | 0.5579 | −0.0522 | 0.1523 | 0.050* | |
C8 | 0.4055 (3) | 0.3291 (5) | −0.1034 (3) | 0.0600 (13) | |
H8A | 0.3962 | 0.4382 | −0.1210 | 0.072* | |
H8B | 0.3516 | 0.2714 | −0.1382 | 0.072* | |
C9 | 0.4157 (3) | 0.3193 (5) | −0.0138 (3) | 0.0526 (12) | |
H9A | 0.4735 | 0.3645 | 0.0223 | 0.063* | |
H9B | 0.3682 | 0.3806 | −0.0071 | 0.063* | |
C10 | 0.4189 (3) | 0.1401 (6) | 0.1013 (3) | 0.0557 (12) | |
H10A | 0.4714 | 0.1980 | 0.1387 | 0.067* | |
H10B | 0.3654 | 0.1834 | 0.1062 | 0.067* | |
C11 | 0.4283 (3) | −0.0287 (6) | 0.1249 (3) | 0.0565 (12) | |
H11A | 0.4377 | −0.0403 | 0.1834 | 0.068* | |
H11B | 0.3737 | −0.0852 | 0.0906 | 0.068* | |
C12 | 0.5150 (3) | −0.2662 (5) | 0.1197 (3) | 0.0545 (12) | |
H12A | 0.4595 | −0.3137 | 0.0802 | 0.065* | |
H12B | 0.5219 | −0.2958 | 0.1759 | 0.065* | |
C13 | 0.3090 (2) | −0.1448 (4) | −0.1038 (2) | 0.0366 (9) | |
C14 | 0.2588 (3) | −0.2852 (5) | −0.1506 (3) | 0.0576 (13) | |
H14A | 0.1997 | −0.2540 | −0.1899 | 0.086* | |
H14B | 0.2527 | −0.3599 | −0.1117 | 0.086* | |
H14C | 0.2916 | −0.3321 | −0.1804 | 0.086* | |
Cl | 0.31158 (9) | 0.51504 (14) | 0.17560 (8) | 0.0584 (3) | |
O5 | 0.3699 (4) | 0.6269 (7) | 0.2282 (4) | 0.135 (2) | |
O6 | 0.3098 (4) | 0.5158 (6) | 0.0945 (3) | 0.1171 (18) | |
O7 | 0.2216 (3) | 0.5651 (6) | 0.1679 (3) | 0.1184 (17) | |
O8 | 0.3259 (3) | 0.3683 (5) | 0.2134 (3) | 0.1128 (16) | |
O9 | 0.0709 (2) | 0.5285 (3) | 0.28972 (19) | 0.0508 (8) | |
H9WA | 0.0613 | 0.5829 | 0.2434 | 0.073 (16)* | |
H9WB | 0.1307 | 0.5167 | 0.3184 | 0.10 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0259 (4) | 0.0280 (4) | 0.0273 (4) | 0.0048 (3) | 0.0111 (3) | 0.0044 (3) |
O1 | 0.0397 (15) | 0.0389 (15) | 0.0398 (15) | −0.0022 (12) | 0.0162 (13) | 0.0127 (12) |
O2 | 0.0449 (18) | 0.074 (2) | 0.067 (2) | 0.0167 (15) | 0.0273 (16) | 0.0418 (17) |
N1 | 0.049 (2) | 0.0316 (17) | 0.0346 (18) | 0.0024 (14) | 0.0195 (15) | 0.0019 (13) |
N2 | 0.0284 (16) | 0.0414 (18) | 0.0381 (18) | 0.0093 (13) | 0.0143 (14) | 0.0161 (14) |
C1 | 0.077 (3) | 0.039 (2) | 0.053 (3) | 0.020 (2) | 0.038 (3) | 0.004 (2) |
C2 | 0.059 (3) | 0.047 (3) | 0.042 (2) | −0.015 (2) | 0.016 (2) | −0.009 (2) |
C3 | 0.043 (3) | 0.071 (3) | 0.037 (2) | −0.012 (2) | −0.002 (2) | 0.002 (2) |
C4 | 0.031 (2) | 0.073 (3) | 0.050 (3) | 0.002 (2) | 0.010 (2) | 0.019 (2) |
C5 | 0.048 (3) | 0.059 (3) | 0.051 (3) | 0.030 (2) | 0.029 (2) | 0.020 (2) |
C6 | 0.046 (2) | 0.030 (2) | 0.041 (2) | −0.0015 (17) | 0.0254 (19) | 0.0028 (17) |
C7 | 0.054 (3) | 0.048 (3) | 0.060 (3) | −0.006 (2) | 0.032 (2) | 0.008 (2) |
Mn2 | 0.0239 (4) | 0.0317 (4) | 0.0368 (5) | 0.0003 (3) | 0.0103 (3) | −0.0059 (3) |
O3 | 0.0288 (14) | 0.0404 (16) | 0.0572 (19) | −0.0048 (11) | 0.0104 (13) | −0.0111 (13) |
O4 | 0.0306 (15) | 0.0455 (18) | 0.068 (2) | −0.0027 (12) | 0.0112 (14) | −0.0175 (14) |
N3 | 0.0263 (16) | 0.0394 (19) | 0.051 (2) | 0.0003 (14) | 0.0104 (15) | −0.0141 (15) |
N4 | 0.0379 (18) | 0.046 (2) | 0.0399 (19) | −0.0079 (15) | 0.0129 (15) | −0.0059 (15) |
C8 | 0.053 (3) | 0.038 (2) | 0.072 (3) | 0.007 (2) | 0.007 (2) | 0.009 (2) |
C9 | 0.036 (2) | 0.035 (2) | 0.078 (3) | 0.0042 (18) | 0.014 (2) | −0.012 (2) |
C10 | 0.047 (3) | 0.064 (3) | 0.064 (3) | 0.001 (2) | 0.031 (2) | −0.022 (2) |
C11 | 0.054 (3) | 0.074 (3) | 0.053 (3) | −0.007 (2) | 0.034 (2) | −0.008 (2) |
C12 | 0.052 (3) | 0.048 (3) | 0.056 (3) | −0.004 (2) | 0.013 (2) | 0.010 (2) |
C13 | 0.031 (2) | 0.037 (2) | 0.043 (2) | −0.0075 (17) | 0.0159 (18) | −0.0045 (17) |
C14 | 0.035 (2) | 0.045 (3) | 0.082 (4) | −0.0107 (19) | 0.013 (2) | −0.016 (2) |
Cl | 0.0691 (8) | 0.0525 (7) | 0.0457 (6) | 0.0054 (6) | 0.0145 (6) | 0.0030 (5) |
O5 | 0.131 (4) | 0.141 (5) | 0.128 (5) | −0.054 (4) | 0.047 (4) | −0.053 (4) |
O6 | 0.146 (4) | 0.147 (4) | 0.059 (3) | 0.073 (3) | 0.042 (3) | 0.010 (3) |
O7 | 0.092 (3) | 0.142 (4) | 0.137 (4) | 0.043 (3) | 0.062 (3) | 0.036 (4) |
O8 | 0.128 (4) | 0.089 (3) | 0.113 (4) | 0.017 (3) | 0.038 (3) | 0.035 (3) |
O9 | 0.0491 (19) | 0.062 (2) | 0.0436 (17) | 0.0016 (14) | 0.0206 (15) | 0.0116 (15) |
Mn1—N1i | 2.037 (3) | Mn2—N4 | 2.045 (3) |
Mn1—N1 | 2.037 (3) | Mn2—O3ii | 2.124 (2) |
Mn1—N2 | 2.038 (3) | Mn2—O3 | 2.124 (2) |
Mn1—N2i | 2.038 (3) | O3—C13 | 1.274 (4) |
Mn1—O1i | 2.122 (2) | O4—C13 | 1.232 (4) |
Mn1—O1 | 2.122 (2) | N3—C9 | 1.482 (5) |
O1—C6 | 1.260 (4) | N3—C10 | 1.497 (6) |
O2—C6 | 1.239 (5) | N3—H3 | 0.910 |
N1—C1 | 1.478 (5) | N4—C12 | 1.483 (5) |
N1—C2 | 1.485 (5) | N4—C11 | 1.485 (5) |
N1—H1 | 0.910 | N4—H4 | 0.910 |
N2—C4 | 1.463 (5) | C8—C9 | 1.498 (7) |
N2—C5 | 1.487 (5) | C8—C12ii | 1.511 (6) |
N2—H2 | 0.910 | C8—H8A | 0.970 |
C1—C5i | 1.511 (6) | C8—H8B | 0.970 |
C1—H1A | 0.970 | C9—H9A | 0.970 |
C1—H1B | 0.970 | C9—H9B | 0.970 |
C2—C3 | 1.505 (6) | C10—C11 | 1.486 (6) |
C2—H2A | 0.970 | C10—H10A | 0.970 |
C2—H2B | 0.970 | C10—H10B | 0.970 |
C3—C4 | 1.507 (7) | C11—H11A | 0.970 |
C3—H3A | 0.970 | C11—H11B | 0.970 |
C3—H3B | 0.970 | C12—C8ii | 1.511 (6) |
C4—H4A | 0.970 | C12—H12A | 0.970 |
C4—H4B | 0.970 | C12—H12B | 0.970 |
C5—C1i | 1.511 (6) | C13—C14 | 1.490 (5) |
C5—H5A | 0.970 | C14—H14A | 0.960 |
C5—H5B | 0.970 | C14—H14B | 0.960 |
C6—C7 | 1.503 (5) | C14—H14C | 0.960 |
C7—H7A | 0.960 | Cl—O8 | 1.386 (4) |
C7—H7B | 0.960 | Cl—O5 | 1.391 (5) |
C7—H7C | 0.960 | Cl—O6 | 1.395 (5) |
Mn2—N3ii | 2.023 (3) | Cl—O7 | 1.462 (4) |
Mn2—N3 | 2.023 (3) | O9—H9WA | 0.89 |
Mn2—N4ii | 2.045 (3) | O9—H9WB | 0.90 |
N1i—Mn1—N1 | 180.00 (18) | N3—Mn2—N4 | 85.90 (14) |
N1i—Mn1—N2 | 85.98 (13) | N4ii—Mn2—N4 | 180.0 (2) |
N1—Mn1—N2 | 94.02 (13) | N3ii—Mn2—O3ii | 91.82 (11) |
N1i—Mn1—N2i | 94.02 (13) | N3—Mn2—O3ii | 88.18 (11) |
N1—Mn1—N2i | 85.98 (13) | N4ii—Mn2—O3ii | 89.66 (12) |
N2—Mn1—N2i | 180.00 (12) | N4—Mn2—O3ii | 90.34 (12) |
N1i—Mn1—O1i | 89.66 (12) | N3ii—Mn2—O3 | 88.18 (11) |
N1—Mn1—O1i | 90.34 (12) | N3—Mn2—O3 | 91.82 (11) |
N2—Mn1—O1i | 87.21 (11) | N4ii—Mn2—O3 | 90.34 (12) |
N2i—Mn1—O1i | 92.79 (11) | N4—Mn2—O3 | 89.66 (12) |
N1i—Mn1—O1 | 90.34 (12) | O3ii—Mn2—O3 | 180.0 |
N1—Mn1—O1 | 89.66 (12) | C13—O3—Mn2 | 132.5 (2) |
N2—Mn1—O1 | 92.79 (11) | C9—N3—C10 | 113.8 (3) |
N2i—Mn1—O1 | 87.21 (11) | C9—N3—Mn2 | 117.2 (3) |
O1i—Mn1—O1 | 180.00 (13) | C10—N3—Mn2 | 106.2 (2) |
C6—O1—Mn1 | 133.5 (3) | C9—N3—H3 | 106.3 |
C1—N1—C2 | 113.0 (3) | C10—N3—H3 | 106.3 |
C1—N1—Mn1 | 105.8 (2) | Mn2—N3—H3 | 106.3 |
C2—N1—Mn1 | 116.8 (2) | C12—N4—C11 | 113.2 (3) |
C1—N1—H1 | 106.9 | C12—N4—Mn2 | 116.7 (3) |
C2—N1—H1 | 106.9 | C11—N4—Mn2 | 106.0 (3) |
Mn1—N1—H1 | 106.9 | C12—N4—H4 | 106.8 |
C4—N2—C5 | 113.0 (3) | C11—N4—H4 | 106.8 |
C4—N2—Mn1 | 116.8 (2) | Mn2—N4—H4 | 106.8 |
C5—N2—Mn1 | 105.9 (2) | C9—C8—C12ii | 114.9 (4) |
C4—N2—H2 | 106.9 | C9—C8—H8A | 108.5 |
C5—N2—H2 | 106.9 | C12ii—C8—H8A | 108.5 |
Mn1—N2—H2 | 106.9 | C9—C8—H8B | 108.5 |
N1—C1—C5i | 108.3 (3) | C12ii—C8—H8B | 108.5 |
N1—C1—H1A | 110.0 | H8A—C8—H8B | 107.5 |
C5i—C1—H1A | 110.0 | N3—C9—C8 | 112.0 (3) |
N1—C1—H1B | 110.0 | N3—C9—H9A | 109.2 |
C5i—C1—H1B | 110.0 | C8—C9—H9A | 109.2 |
H1A—C1—H1B | 108.4 | N3—C9—H9B | 109.2 |
N1—C2—C3 | 111.9 (3) | C8—C9—H9B | 109.2 |
N1—C2—H2A | 109.2 | H9A—C9—H9B | 107.9 |
C3—C2—H2A | 109.2 | C11—C10—N3 | 108.9 (3) |
N1—C2—H2B | 109.2 | C11—C10—H10A | 109.9 |
C3—C2—H2B | 109.2 | N3—C10—H10A | 109.9 |
H2A—C2—H2B | 107.9 | C11—C10—H10B | 109.9 |
C2—C3—C4 | 115.2 (4) | N3—C10—H10B | 109.9 |
C2—C3—H3A | 108.5 | H10A—C10—H10B | 108.3 |
C4—C3—H3A | 108.5 | N4—C11—C10 | 108.2 (4) |
C2—C3—H3B | 108.5 | N4—C11—H11A | 110.1 |
C4—C3—H3B | 108.5 | C10—C11—H11A | 110.1 |
H3A—C3—H3B | 107.5 | N4—C11—H11B | 110.1 |
N2—C4—C3 | 113.2 (3) | C10—C11—H11B | 110.1 |
N2—C4—H4A | 108.9 | H11A—C11—H11B | 108.4 |
C3—C4—H4A | 108.9 | N4—C12—C8ii | 112.2 (4) |
N2—C4—H4B | 108.9 | N4—C12—H12A | 109.2 |
C3—C4—H4B | 108.9 | C8ii—C12—H12A | 109.2 |
H4A—C4—H4B | 107.8 | N4—C12—H12B | 109.2 |
N2—C5—C1i | 107.4 (3) | C8ii—C12—H12B | 109.2 |
N2—C5—H5A | 110.2 | H12A—C12—H12B | 107.9 |
C1i—C5—H5A | 110.2 | O4—C13—O3 | 124.7 (3) |
N2—C5—H5B | 110.2 | O4—C13—C14 | 119.6 (3) |
C1i—C5—H5B | 110.2 | O3—C13—C14 | 115.7 (3) |
H5A—C5—H5B | 108.5 | C13—C14—H14A | 109.5 |
O2—C6—O1 | 124.1 (3) | C13—C14—H14B | 109.5 |
O2—C6—C7 | 120.0 (3) | H14A—C14—H14B | 109.5 |
O1—C6—C7 | 115.9 (4) | C13—C14—H14C | 109.5 |
C6—C7—H7A | 109.5 | H14A—C14—H14C | 109.5 |
C6—C7—H7B | 109.5 | H14B—C14—H14C | 109.5 |
H7A—C7—H7B | 109.5 | O8—Cl—O5 | 111.4 (4) |
C6—C7—H7C | 109.5 | O8—Cl—O6 | 114.4 (3) |
H7A—C7—H7C | 109.5 | O5—Cl—O6 | 113.3 (4) |
H7B—C7—H7C | 109.5 | O8—Cl—O7 | 106.1 (3) |
N3ii—Mn2—N3 | 180.00 (19) | O5—Cl—O7 | 104.2 (4) |
N3ii—Mn2—N4ii | 85.90 (14) | O6—Cl—O7 | 106.5 (3) |
N3—Mn2—N4ii | 94.10 (14) | H9WA—O9—H9WB | 108.9 |
N3ii—Mn2—N4 | 94.10 (14) | ||
N1i—Mn1—O1—C6 | 102.2 (4) | N3ii—Mn2—O3—C13 | −162.3 (4) |
N1—Mn1—O1—C6 | −77.8 (4) | N3—Mn2—O3—C13 | 17.7 (4) |
N2—Mn1—O1—C6 | 16.2 (4) | N4ii—Mn2—O3—C13 | −76.4 (4) |
N2i—Mn1—O1—C6 | −163.8 (4) | N4—Mn2—O3—C13 | 103.6 (4) |
N2—Mn1—N1—C1 | 165.2 (3) | N4ii—Mn2—N3—C9 | −38.1 (3) |
N2i—Mn1—N1—C1 | −14.8 (3) | N4—Mn2—N3—C9 | 141.9 (3) |
O1i—Mn1—N1—C1 | 77.9 (3) | O3ii—Mn2—N3—C9 | 51.4 (3) |
O1—Mn1—N1—C1 | −102.1 (3) | O3—Mn2—N3—C9 | −128.6 (3) |
N2—Mn1—N1—C2 | 38.4 (3) | N4ii—Mn2—N3—C10 | −166.6 (3) |
N2i—Mn1—N1—C2 | −141.6 (3) | N4—Mn2—N3—C10 | 13.4 (3) |
O1i—Mn1—N1—C2 | −48.8 (3) | O3ii—Mn2—N3—C10 | −77.1 (3) |
O1—Mn1—N1—C2 | 131.2 (3) | O3—Mn2—N3—C10 | 102.9 (3) |
N1i—Mn1—N2—C4 | 142.1 (3) | N3ii—Mn2—N4—C12 | −37.6 (3) |
N1—Mn1—N2—C4 | −37.9 (3) | N3—Mn2—N4—C12 | 142.4 (3) |
O1i—Mn1—N2—C4 | 52.2 (3) | O3ii—Mn2—N4—C12 | −129.4 (3) |
O1—Mn1—N2—C4 | −127.8 (3) | O3—Mn2—N4—C12 | 50.6 (3) |
N1i—Mn1—N2—C5 | 15.3 (3) | N3ii—Mn2—N4—C11 | −164.7 (3) |
N1—Mn1—N2—C5 | −164.7 (3) | N3—Mn2—N4—C11 | 15.3 (3) |
O1i—Mn1—N2—C5 | −74.5 (3) | O3ii—Mn2—N4—C11 | 103.5 (3) |
O1—Mn1—N2—C5 | 105.5 (3) | O3—Mn2—N4—C11 | −76.5 (3) |
C2—N1—C1—C5i | 171.3 (3) | C10—N3—C9—C8 | −178.8 (3) |
Mn1—N1—C1—C5i | 42.3 (4) | Mn2—N3—C9—C8 | 56.4 (4) |
C1—N1—C2—C3 | −179.1 (4) | C12ii—C8—C9—N3 | −70.3 (5) |
Mn1—N1—C2—C3 | −56.0 (4) | C9—N3—C10—C11 | −170.8 (3) |
N1—C2—C3—C4 | 69.2 (5) | Mn2—N3—C10—C11 | −40.4 (4) |
C5—N2—C4—C3 | 178.6 (3) | C12—N4—C11—C10 | −170.8 (4) |
Mn1—N2—C4—C3 | 55.4 (4) | Mn2—N4—C11—C10 | −41.7 (4) |
C2—C3—C4—N2 | −69.4 (5) | N3—C10—C11—N4 | 55.9 (5) |
C4—N2—C5—C1i | −171.3 (3) | C11—N4—C12—C8ii | 178.6 (4) |
Mn1—N2—C5—C1i | −42.3 (3) | Mn2—N4—C12—C8ii | 55.2 (4) |
Mn1—O1—C6—O2 | −9.6 (6) | Mn2—O3—C13—O4 | −6.9 (6) |
Mn1—O1—C6—C7 | 170.8 (3) | Mn2—O3—C13—C14 | 174.0 (3) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O9iii | 0.91 | 2.04 | 2.916 (4) | 163 |
N2—H2···O2 | 0.91 | 2.03 | 2.865 (4) | 153 |
N3—H3···O4 | 0.91 | 1.98 | 2.831 (4) | 155 |
N4—H4···O5iv | 0.91 | 2.46 | 3.283 (7) | 151 |
N4—H4···O8iv | 0.91 | 2.43 | 3.171 (6) | 139 |
O9—H9WA···O2 | 0.89 | 1.92 | 2.794 (4) | 171 |
O9—H9WB···O4v | 0.90 | 2.07 | 2.954 (4) | 170 |
Symmetry codes: (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C2H3O2)2(C10H24N4)]ClO4·H2O |
Mr | 490.83 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.0734 (17), 8.5147 (9), 17.3393 (18) |
β (°) | 113.446 (2) |
V (Å3) | 2177.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.78 |
Crystal size (mm) | 0.26 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.747, 0.889 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12476, 4452, 3154 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.172, 1.06 |
No. of reflections | 4452 |
No. of parameters | 269 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.20, −0.66 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O9i | 0.91 | 2.04 | 2.916 (4) | 162.6 |
N2—H2···O2 | 0.91 | 2.03 | 2.865 (4) | 152.9 |
N3—H3···O4 | 0.91 | 1.98 | 2.831 (4) | 155.1 |
N4—H4···O5ii | 0.91 | 2.46 | 3.283 (7) | 150.6 |
N4—H4···O8ii | 0.91 | 2.43 | 3.171 (6) | 138.6 |
O9—H9WA···O2 | 0.89 | 1.92 | 2.794 (4) | 171.0 |
O9—H9WB···O4iii | 0.90 | 2.07 | 2.954 (4) | 169.5 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2. |
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The structure of the title compound contains two chemically equivalent, but crystallographically independent, cationic complexes, both located with their central MnIII atom on a centre of inversion (Fig. 1). In both cations, the MnIII atom is six-coordinated in a distorted octahedral geometry by two O atoms from acetato anions occupying axial positions and four N atoms from 1,4,8,11-tetraazacyclotetradecane (cyclam) occupying equatorial positions (mean lengths: Mn—N 2.036 Å, Mn—O 2.123 Å). The compound displays intra- and intermolecular hydrogen bonding (Fig. 2 & Table 1).