Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042249/rk2035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042249/rk2035Isup2.hkl |
CCDC reference: 663555
Key indicators
- Single-crystal X-ray study
- T = 243 K
- Mean (C-C) = 0.009 Å
- R factor = 0.044
- wR factor = 0.137
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.07 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 2.853 Test value = 2.625 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 2.85 e/A PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.92 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C27 - C28 .. 6.60 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C7 - C12 ... 1.43 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C9 - C10 ... 1.42 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 79.00 A 3
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C25 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C30 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 2.14 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn2 (2) 1.93
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 14 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 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
For some other Mn(bpic) complexes, see: Lu et al. (2006); Schoumacker et al. (2003).
A solution of MnBr2 (0.37 g, 1.72 mmol) and N,N'-bis(2-pyridylmethylidene)-1,2-diiminocyclohexane (0.50 g, 1.71 mmol) in EtOH (30 ml) was stirred for 1 h at room temparature. After add of diethyl ether to the solution, the formed precipitate was separated by filtration and washed with acetone and dried under vacuum, to give a dark yellow powder (0.45 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a EtOH solution. MS (FAB): m/z 426, 428 [Mn(bpic)Br+]; IR (KBr): 3376 cm-1 (broad).
H atoms were positioned geometrically and allowed to ride on their respective carrier atoms [C—H = 0.94, 0.98 or 0.99 Å and Uiso(H) = 1.2Ueq(C)]. The H atoms of the water ligands were located from Fourier difference maps, but not refined [Uiso(H) = 0.08 Å2].
The CIF check program indicates a high ratio of the maximum and minimum residual density (4.07) in the structure and solvent accessible voids of 79 Å3. All these factors indicate a strong likelihood of disordered solvent molecule MeOH in the structure. However, the solvent molecule could neither be located nor refined, because the highest difference peak (2.85 e Å-3) lies on a special position (0, 0, 0) with the site occupation factor 0.5. The distance between this peak and the nearest atom is 1.433 Å.
The crystal structure of the title compound, [MnBr2(C18H20N4)][MnBr(C18H20N4)(H2O)2]Br, consists of two different MnII complexes in an asymmetric unit (Fig. 1). In one neutral complex, Mn2+ ion is six-coordinated in a distorted octahedral environment by four N atoms from the tetradentate ligand N,N'-bis(2-pyridylmethylidene)-1,2-diiminocyclohexane (bpic) occupying equatorial positions and two Br atoms occupying axial positions. Within the equatorial plane, the chelating angles lie in the range of 70.69 (16)–71.98 (16)°. The apical Br1—Mn1—Br2 bond angle is 151.60 (4)°. In the other cation complex, Mn2+ ion is seven-coordinated in an approximately pentagonal bipyramidal structure by four N atoms from bpic, one Br atom and two O atoms from water ligands. The four N atoms and one O atom occupy the equatorial positions, and the Br atom and one O atom lie in the axial positions. Within the equatorial plane, the chelating angles lie in the range of 68.66 (17)–69.23 (16)°. The apical Br3—Mn2—O1 bond angle is 170.10 (10)°. The compound displays intermolecular hydrogen bonds between the O atoms and the Br atoms (Br1, Br4) (Fig. 2). Moreover, there are intermolecular π–π interactions between the adjacent pyridine rings. The distances between Cg1 (the centroid of six-membered ring N1–C5) and Cg4iii [ring N8–C36; symmetry code: (iii) 1 - x, 1 - y, -z], and between Cg2 (ring N4–C18) and Cg3iv [ring N5–C23; symmetry code: (iv) 1 - x, 2 - y, 1 - z] are 3.604 Å and 3.680 Å, repectively, with the respective dihedral angles between the ring planes 4.7° and 5.0°.
For some other Mn(bpic) complexes, see: Lu et al. (2006); Schoumacker et al. (2003).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 1997).
[MnBr(C18H20N4)(H2O)2]Br·[MnBr2(C18H20N4)] | Z = 2 |
Mr = 1050.27 | F(000) = 1044 |
Triclinic, P1 | Dx = 1.706 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8283 (9) Å | Cell parameters from 4110 reflections |
b = 12.4842 (9) Å | θ = 2.2–26.3° |
c = 14.134 (1) Å | µ = 4.57 mm−1 |
α = 97.971 (1)° | T = 243 K |
β = 91.017 (1)° | Plate, yellow |
γ = 98.036 (1)° | 0.15 × 0.10 × 0.10 mm |
V = 2045.2 (3) Å3 |
Bruker SMART 1000 CCD area-detector diffractometer | 8169 independent reflections |
Radiation source: fine-focus sealed tube | 5661 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −14→13 |
Tmin = 0.520, Tmax = 0.633 | k = −15→15 |
12149 measured reflections | l = −17→16 |
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) = 0.137 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0737P)2] where P = (Fo2 + 2Fc2)/3 |
8169 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 2.85 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
[MnBr(C18H20N4)(H2O)2]Br·[MnBr2(C18H20N4)] | γ = 98.036 (1)° |
Mr = 1050.27 | V = 2045.2 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.8283 (9) Å | Mo Kα radiation |
b = 12.4842 (9) Å | µ = 4.57 mm−1 |
c = 14.134 (1) Å | T = 243 K |
α = 97.971 (1)° | 0.15 × 0.10 × 0.10 mm |
β = 91.017 (1)° |
Bruker SMART 1000 CCD area-detector diffractometer | 8169 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5661 reflections with I > 2σ(I) |
Tmin = 0.520, Tmax = 0.633 | Rint = 0.019 |
12149 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | Δρmax = 2.85 e Å−3 |
8169 reflections | Δρmin = −0.70 e Å−3 |
469 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 | 0.76129 (7) | 0.66873 (7) | 0.07222 (6) | 0.0291 (2) | |
Br1 | 0.97942 (5) | 0.75164 (5) | 0.12675 (4) | 0.03992 (17) | |
Br2 | 0.56467 (5) | 0.68502 (6) | −0.00236 (4) | 0.04501 (18) | |
N1 | 0.8298 (4) | 0.6500 (4) | −0.0837 (3) | 0.0302 (10) | |
N2 | 0.8074 (4) | 0.5001 (4) | 0.0341 (3) | 0.0385 (12) | |
N3 | 0.7153 (4) | 0.5746 (4) | 0.1928 (3) | 0.0358 (11) | |
N4 | 0.7117 (4) | 0.7889 (4) | 0.1988 (3) | 0.0314 (10) | |
C1 | 0.8331 (5) | 0.7196 (5) | −0.1462 (4) | 0.0418 (15) | |
H1 | 0.8147 | 0.7899 | −0.1260 | 0.050* | |
C2 | 0.8623 (5) | 0.6940 (6) | −0.2398 (5) | 0.0487 (17) | |
H2 | 0.8610 | 0.7451 | −0.2826 | 0.058* | |
C3 | 0.8929 (5) | 0.5949 (5) | −0.2694 (4) | 0.0441 (15) | |
H3 | 0.9143 | 0.5764 | −0.3327 | 0.053* | |
C4 | 0.8921 (5) | 0.5211 (5) | −0.2047 (4) | 0.0376 (14) | |
H4 | 0.9141 | 0.4519 | −0.2226 | 0.045* | |
C5 | 0.8588 (4) | 0.5516 (4) | −0.1147 (4) | 0.0310 (12) | |
C6 | 0.8508 (5) | 0.4744 (5) | −0.0451 (4) | 0.0370 (14) | |
H6 | 0.8775 | 0.4067 | −0.0594 | 0.044* | |
C7 | 0.8060 (7) | 0.4325 (6) | 0.1111 (5) | 0.068 (2) | |
H7 | 0.8790 | 0.4593 | 0.1478 | 0.081* | |
C8 | 0.8103 (6) | 0.3115 (5) | 0.0798 (5) | 0.0511 (17) | |
H8A | 0.7484 | 0.2820 | 0.0323 | 0.061* | |
H8B | 0.8831 | 0.3024 | 0.0497 | 0.061* | |
C9 | 0.7984 (8) | 0.2488 (7) | 0.1641 (6) | 0.089 (3) | |
H9A | 0.7780 | 0.1711 | 0.1394 | 0.107* | |
H9B | 0.8734 | 0.2577 | 0.1971 | 0.107* | |
C10 | 0.7176 (8) | 0.2776 (6) | 0.2329 (6) | 0.084 (3) | |
H10A | 0.7332 | 0.2456 | 0.2904 | 0.101* | |
H10B | 0.6415 | 0.2434 | 0.2075 | 0.101* | |
C11 | 0.7136 (5) | 0.3963 (5) | 0.2621 (4) | 0.0383 (14) | |
H11A | 0.7776 | 0.4269 | 0.3072 | 0.046* | |
H11B | 0.6425 | 0.4055 | 0.2949 | 0.046* | |
C12 | 0.7199 (7) | 0.4588 (6) | 0.1767 (5) | 0.064 (2) | |
H12 | 0.6478 | 0.4288 | 0.1398 | 0.077* | |
C13 | 0.6838 (4) | 0.6249 (5) | 0.2698 (4) | 0.0324 (13) | |
H13 | 0.6667 | 0.5880 | 0.3226 | 0.039* | |
C14 | 0.6747 (4) | 0.7403 (5) | 0.2754 (4) | 0.0328 (13) | |
C15 | 0.6282 (4) | 0.7954 (5) | 0.3528 (4) | 0.0360 (13) | |
H15 | 0.6035 | 0.7593 | 0.4044 | 0.043* | |
C16 | 0.6186 (5) | 0.9029 (5) | 0.3537 (4) | 0.0411 (15) | |
H16 | 0.5872 | 0.9424 | 0.4059 | 0.049* | |
C17 | 0.6555 (5) | 0.9524 (5) | 0.2770 (5) | 0.0426 (15) | |
H17 | 0.6496 | 1.0265 | 0.2755 | 0.051* | |
C18 | 0.7022 (5) | 0.8907 (5) | 0.2007 (4) | 0.0398 (14) | |
H18 | 0.7278 | 0.9254 | 0.1484 | 0.048* | |
Mn2 | 0.25348 (7) | 0.76805 (6) | 0.42552 (6) | 0.0291 (2) | |
Br3 | 0.42980 (5) | 0.81252 (5) | 0.54720 (4) | 0.03697 (16) | |
Br4 | 0.12914 (5) | 0.36444 (5) | 0.52829 (5) | 0.04494 (18) | |
N5 | 0.1501 (4) | 0.8781 (4) | 0.5369 (3) | 0.0335 (11) | |
N6 | 0.2646 (4) | 0.9444 (4) | 0.3879 (3) | 0.0326 (11) | |
N7 | 0.3127 (4) | 0.7766 (4) | 0.2688 (3) | 0.0364 (11) | |
N8 | 0.3411 (4) | 0.6112 (4) | 0.3653 (4) | 0.0376 (12) | |
C19 | 0.0984 (5) | 0.8510 (5) | 0.6154 (4) | 0.0404 (14) | |
H19 | 0.0938 | 0.7783 | 0.6273 | 0.048* | |
C20 | 0.0512 (5) | 0.9247 (6) | 0.6804 (5) | 0.0453 (15) | |
H20 | 0.0175 | 0.9019 | 0.7353 | 0.054* | |
C21 | 0.0538 (5) | 1.0317 (5) | 0.6639 (5) | 0.0420 (15) | |
H21 | 0.0215 | 1.0826 | 0.7065 | 0.050* | |
C22 | 0.1053 (5) | 1.0610 (5) | 0.5828 (4) | 0.0393 (14) | |
H22 | 0.1074 | 1.1326 | 0.5685 | 0.047* | |
C23 | 0.1544 (4) | 0.9839 (5) | 0.5219 (4) | 0.0332 (13) | |
C24 | 0.2162 (4) | 1.0140 (5) | 0.4385 (4) | 0.0345 (13) | |
H24 | 0.2196 | 1.0852 | 0.4229 | 0.041* | |
C25 | 0.3296 (5) | 0.9712 (5) | 0.3049 (4) | 0.0364 (14) | |
H25 | 0.4117 | 0.9753 | 0.3224 | 0.044* | |
C26 | 0.3135 (5) | 1.0776 (5) | 0.2695 (5) | 0.0504 (17) | |
H26A | 0.2326 | 1.0770 | 0.2530 | 0.061* | |
H26B | 0.3372 | 1.1390 | 0.3203 | 0.061* | |
C27 | 0.3832 (6) | 1.0917 (7) | 0.1833 (6) | 0.069 (2) | |
H27A | 0.3719 | 1.1604 | 0.1609 | 0.083* | |
H27B | 0.4644 | 1.0962 | 0.2011 | 0.083* | |
C28 | 0.3511 (7) | 0.9993 (6) | 0.1042 (5) | 0.066 (2) | |
H28A | 0.3979 | 1.0110 | 0.0490 | 0.079* | |
H28B | 0.2707 | 0.9962 | 0.0844 | 0.079* | |
C29 | 0.3693 (6) | 0.8919 (6) | 0.1379 (5) | 0.0551 (18) | |
H29A | 0.4505 | 0.8932 | 0.1537 | 0.066* | |
H29B | 0.3458 | 0.8311 | 0.0866 | 0.066* | |
C30 | 0.2990 (5) | 0.8754 (5) | 0.2262 (4) | 0.0376 (14) | |
H30 | 0.2172 | 0.8716 | 0.2076 | 0.045* | |
C31 | 0.3557 (5) | 0.6978 (5) | 0.2261 (4) | 0.0422 (15) | |
H31 | 0.3795 | 0.6999 | 0.1632 | 0.051* | |
C32 | 0.3693 (4) | 0.6028 (5) | 0.2731 (4) | 0.0373 (14) | |
C33 | 0.4082 (5) | 0.5137 (5) | 0.2263 (5) | 0.0474 (17) | |
H33 | 0.4260 | 0.5104 | 0.1615 | 0.057* | |
C34 | 0.4213 (5) | 0.4281 (6) | 0.2752 (6) | 0.058 (2) | |
H34 | 0.4455 | 0.3643 | 0.2438 | 0.069* | |
C35 | 0.3987 (5) | 0.4372 (5) | 0.3691 (6) | 0.0561 (19) | |
H35 | 0.4105 | 0.3812 | 0.4046 | 0.067* | |
C36 | 0.3580 (5) | 0.5294 (5) | 0.4122 (5) | 0.0437 (15) | |
H36 | 0.3415 | 0.5346 | 0.4774 | 0.052* | |
O1 | 0.0812 (3) | 0.7290 (3) | 0.3424 (3) | 0.0405 (10) | |
H1W | 0.0595 | 0.7353 | 0.2792 | 0.080* | |
H2W | 0.0187 | 0.7035 | 0.3659 | 0.080* | |
O2 | 0.1481 (3) | 0.6340 (3) | 0.5022 (3) | 0.0424 (10) | |
H3W | 0.1576 | 0.5634 | 0.5037 | 0.080* | |
H4W | 0.0767 | 0.6311 | 0.5019 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0353 (5) | 0.0276 (5) | 0.0254 (5) | 0.0090 (4) | 0.0041 (3) | 0.0021 (3) |
Br1 | 0.0350 (3) | 0.0481 (4) | 0.0344 (3) | 0.0081 (3) | 0.0011 (2) | −0.0039 (3) |
Br2 | 0.0384 (3) | 0.0614 (4) | 0.0355 (4) | 0.0150 (3) | −0.0011 (3) | 0.0000 (3) |
N1 | 0.033 (2) | 0.031 (3) | 0.027 (3) | 0.006 (2) | 0.0000 (19) | 0.005 (2) |
N2 | 0.054 (3) | 0.029 (3) | 0.036 (3) | 0.012 (2) | 0.016 (2) | 0.008 (2) |
N3 | 0.051 (3) | 0.031 (3) | 0.028 (3) | 0.013 (2) | 0.006 (2) | 0.003 (2) |
N4 | 0.032 (2) | 0.031 (3) | 0.031 (3) | 0.009 (2) | 0.002 (2) | −0.002 (2) |
C1 | 0.045 (4) | 0.043 (4) | 0.040 (4) | 0.009 (3) | 0.006 (3) | 0.012 (3) |
C2 | 0.051 (4) | 0.063 (5) | 0.037 (4) | 0.004 (3) | 0.005 (3) | 0.025 (3) |
C3 | 0.042 (4) | 0.061 (4) | 0.028 (3) | 0.004 (3) | 0.006 (3) | 0.002 (3) |
C4 | 0.037 (3) | 0.045 (4) | 0.030 (3) | 0.008 (3) | 0.005 (3) | 0.000 (3) |
C5 | 0.030 (3) | 0.031 (3) | 0.030 (3) | 0.003 (2) | 0.002 (2) | 0.001 (2) |
C6 | 0.046 (3) | 0.029 (3) | 0.037 (4) | 0.012 (3) | 0.010 (3) | −0.001 (3) |
C7 | 0.118 (7) | 0.042 (4) | 0.056 (5) | 0.034 (4) | 0.041 (5) | 0.023 (4) |
C8 | 0.080 (5) | 0.035 (4) | 0.044 (4) | 0.020 (3) | 0.021 (3) | 0.011 (3) |
C9 | 0.148 (9) | 0.050 (5) | 0.091 (7) | 0.047 (5) | 0.056 (6) | 0.039 (5) |
C10 | 0.153 (9) | 0.041 (4) | 0.067 (6) | 0.019 (5) | 0.039 (6) | 0.026 (4) |
C11 | 0.041 (3) | 0.038 (3) | 0.037 (4) | 0.006 (3) | 0.002 (3) | 0.010 (3) |
C12 | 0.119 (6) | 0.039 (4) | 0.041 (4) | 0.029 (4) | 0.024 (4) | 0.012 (3) |
C13 | 0.034 (3) | 0.039 (3) | 0.023 (3) | 0.002 (2) | 0.002 (2) | 0.003 (3) |
C14 | 0.022 (3) | 0.042 (3) | 0.031 (3) | 0.006 (2) | −0.002 (2) | −0.007 (3) |
C15 | 0.028 (3) | 0.044 (4) | 0.033 (3) | 0.004 (3) | 0.000 (2) | −0.006 (3) |
C16 | 0.027 (3) | 0.051 (4) | 0.040 (4) | 0.008 (3) | −0.003 (3) | −0.012 (3) |
C17 | 0.036 (3) | 0.035 (3) | 0.053 (4) | 0.013 (3) | −0.012 (3) | −0.010 (3) |
C18 | 0.041 (3) | 0.038 (4) | 0.039 (4) | 0.009 (3) | −0.001 (3) | −0.001 (3) |
Mn2 | 0.0316 (4) | 0.0273 (5) | 0.0282 (5) | 0.0064 (3) | 0.0025 (3) | 0.0012 (4) |
Br3 | 0.0360 (3) | 0.0412 (4) | 0.0322 (3) | 0.0084 (3) | −0.0008 (2) | −0.0028 (3) |
Br4 | 0.0395 (3) | 0.0471 (4) | 0.0506 (4) | 0.0006 (3) | −0.0001 (3) | 0.0213 (3) |
N5 | 0.034 (3) | 0.032 (3) | 0.034 (3) | 0.007 (2) | −0.002 (2) | 0.000 (2) |
N6 | 0.028 (2) | 0.036 (3) | 0.033 (3) | 0.002 (2) | −0.001 (2) | 0.006 (2) |
N7 | 0.032 (3) | 0.043 (3) | 0.030 (3) | 0.001 (2) | 0.004 (2) | −0.004 (2) |
N8 | 0.035 (3) | 0.033 (3) | 0.042 (3) | 0.005 (2) | 0.003 (2) | −0.006 (2) |
C19 | 0.043 (3) | 0.036 (4) | 0.039 (4) | 0.003 (3) | 0.004 (3) | 0.001 (3) |
C20 | 0.038 (3) | 0.058 (4) | 0.037 (4) | 0.005 (3) | 0.005 (3) | 0.000 (3) |
C21 | 0.033 (3) | 0.041 (4) | 0.047 (4) | 0.010 (3) | −0.001 (3) | −0.013 (3) |
C22 | 0.037 (3) | 0.033 (3) | 0.046 (4) | 0.014 (3) | −0.013 (3) | −0.007 (3) |
C23 | 0.030 (3) | 0.032 (3) | 0.037 (3) | 0.009 (2) | −0.006 (2) | −0.001 (3) |
C24 | 0.030 (3) | 0.030 (3) | 0.043 (4) | 0.002 (2) | −0.006 (3) | 0.006 (3) |
C25 | 0.030 (3) | 0.042 (4) | 0.039 (4) | 0.004 (3) | −0.001 (3) | 0.013 (3) |
C26 | 0.042 (4) | 0.053 (4) | 0.061 (5) | 0.004 (3) | 0.004 (3) | 0.029 (4) |
C27 | 0.048 (4) | 0.086 (6) | 0.086 (6) | 0.011 (4) | 0.007 (4) | 0.056 (5) |
C28 | 0.079 (5) | 0.079 (6) | 0.041 (4) | 0.000 (4) | 0.010 (4) | 0.025 (4) |
C29 | 0.055 (4) | 0.075 (5) | 0.031 (4) | 0.000 (4) | 0.005 (3) | 0.007 (3) |
C30 | 0.034 (3) | 0.049 (4) | 0.029 (3) | 0.001 (3) | −0.001 (2) | 0.008 (3) |
C31 | 0.034 (3) | 0.056 (4) | 0.031 (3) | 0.000 (3) | 0.005 (3) | −0.007 (3) |
C32 | 0.027 (3) | 0.039 (4) | 0.039 (4) | −0.002 (2) | −0.001 (3) | −0.012 (3) |
C33 | 0.030 (3) | 0.048 (4) | 0.056 (4) | 0.003 (3) | 0.007 (3) | −0.022 (3) |
C34 | 0.035 (4) | 0.041 (4) | 0.088 (6) | 0.006 (3) | 0.009 (4) | −0.021 (4) |
C35 | 0.041 (4) | 0.035 (4) | 0.090 (6) | 0.003 (3) | 0.002 (4) | 0.006 (4) |
C36 | 0.040 (3) | 0.034 (4) | 0.056 (4) | 0.008 (3) | 0.005 (3) | 0.001 (3) |
O1 | 0.037 (2) | 0.049 (3) | 0.034 (2) | −0.0017 (19) | 0.0005 (17) | 0.0084 (19) |
O2 | 0.038 (2) | 0.034 (2) | 0.058 (3) | 0.0068 (18) | 0.004 (2) | 0.011 (2) |
Mn1—N3 | 2.234 (4) | Mn2—N7 | 2.346 (5) |
Mn1—N2 | 2.245 (5) | Mn2—N8 | 2.403 (5) |
Mn1—N4 | 2.309 (4) | Mn2—N5 | 2.408 (5) |
Mn1—N1 | 2.354 (4) | Mn2—Br3 | 2.6268 (10) |
Mn1—Br2 | 2.5818 (10) | N5—C19 | 1.338 (7) |
Mn1—Br1 | 2.6988 (10) | N5—C23 | 1.361 (7) |
N1—C1 | 1.320 (7) | N6—C24 | 1.256 (7) |
N1—C5 | 1.339 (7) | N6—C25 | 1.465 (7) |
N2—C6 | 1.259 (7) | N7—C31 | 1.256 (7) |
N2—C7 | 1.466 (8) | N7—C30 | 1.473 (7) |
N3—C13 | 1.268 (7) | N8—C36 | 1.327 (7) |
N3—C12 | 1.441 (8) | N8—C32 | 1.345 (7) |
N4—C18 | 1.289 (7) | C19—C20 | 1.389 (8) |
N4—C14 | 1.363 (7) | C19—H19 | 0.9400 |
C1—C2 | 1.379 (9) | C20—C21 | 1.384 (9) |
C1—H1 | 0.9400 | C20—H20 | 0.9400 |
C2—C3 | 1.350 (9) | C21—C22 | 1.377 (8) |
C2—H2 | 0.9400 | C21—H21 | 0.9400 |
C3—C4 | 1.384 (8) | C22—C23 | 1.395 (8) |
C3—H3 | 0.9400 | C22—H22 | 0.9400 |
C4—C5 | 1.358 (7) | C23—C24 | 1.464 (8) |
C4—H4 | 0.9400 | C24—H24 | 0.9400 |
C5—C6 | 1.466 (7) | C25—C30 | 1.515 (8) |
C6—H6 | 0.9400 | C25—C26 | 1.517 (8) |
C7—C12 | 1.431 (9) | C25—H25 | 0.9900 |
C7—C8 | 1.522 (9) | C26—C27 | 1.501 (9) |
C7—H7 | 0.9900 | C26—H26A | 0.9800 |
C8—C9 | 1.513 (9) | C26—H26B | 0.9800 |
C8—H8A | 0.9800 | C27—C28 | 1.493 (11) |
C8—H8B | 0.9800 | C27—H27A | 0.9800 |
C9—C10 | 1.421 (10) | C27—H27B | 0.9800 |
C9—H9A | 0.9800 | C28—C29 | 1.524 (9) |
C9—H9B | 0.9800 | C28—H28A | 0.9800 |
C10—C11 | 1.490 (9) | C28—H28B | 0.9800 |
C10—H10A | 0.9800 | C29—C30 | 1.534 (8) |
C10—H10B | 0.9800 | C29—H29A | 0.9800 |
C11—C12 | 1.523 (8) | C29—H29B | 0.9800 |
C11—H11A | 0.9800 | C30—H30 | 0.9900 |
C11—H11B | 0.9800 | C31—C32 | 1.463 (9) |
C12—H12 | 0.9900 | C31—H31 | 0.9400 |
C13—C14 | 1.450 (8) | C32—C33 | 1.356 (8) |
C13—H13 | 0.9400 | C33—C34 | 1.374 (10) |
C14—C15 | 1.375 (7) | C33—H33 | 0.9400 |
C15—C16 | 1.361 (8) | C34—C35 | 1.351 (10) |
C15—H15 | 0.9400 | C34—H34 | 0.9400 |
C16—C17 | 1.369 (8) | C35—C36 | 1.379 (9) |
C16—H16 | 0.9400 | C35—H35 | 0.9400 |
C17—C18 | 1.405 (8) | C36—H36 | 0.9400 |
C17—H17 | 0.9400 | O1—H1W | 0.942 |
C18—H18 | 0.9400 | O1—H2W | 0.855 |
Mn2—O1 | 2.291 (4) | O2—H3W | 0.907 |
Mn2—N6 | 2.322 (4) | O2—H4W | 0.840 |
Mn2—O2 | 2.344 (4) | ||
N3—Mn1—N2 | 71.68 (16) | O1—Mn2—N8 | 100.81 (15) |
N3—Mn1—N4 | 71.98 (16) | N6—Mn2—N8 | 134.05 (16) |
N2—Mn1—N4 | 142.60 (17) | O2—Mn2—N8 | 79.55 (15) |
N3—Mn1—N1 | 142.22 (16) | N7—Mn2—N8 | 68.79 (17) |
N2—Mn1—N1 | 70.69 (16) | O1—Mn2—N5 | 83.30 (15) |
N4—Mn1—N1 | 145.68 (16) | N6—Mn2—N5 | 69.23 (16) |
N3—Mn1—Br2 | 102.99 (12) | O2—Mn2—N5 | 78.73 (14) |
N2—Mn1—Br2 | 111.61 (14) | N7—Mn2—N5 | 134.79 (16) |
N4—Mn1—Br2 | 84.99 (11) | N8—Mn2—N5 | 156.11 (16) |
N1—Mn1—Br2 | 87.70 (11) | O1—Mn2—Br3 | 170.10 (10) |
N3—Mn1—Br1 | 99.48 (13) | N6—Mn2—Br3 | 95.07 (11) |
N2—Mn1—Br1 | 91.76 (13) | O2—Mn2—Br3 | 97.15 (11) |
N4—Mn1—Br1 | 85.68 (11) | N7—Mn2—Br3 | 110.61 (12) |
N1—Mn1—Br1 | 85.05 (11) | N8—Mn2—Br3 | 84.23 (12) |
Br2—Mn1—Br1 | 151.60 (4) | N5—Mn2—Br3 | 88.70 (11) |
C1—N1—C5 | 116.7 (5) | C19—N5—C23 | 116.6 (5) |
C1—N1—Mn1 | 128.4 (4) | C19—N5—Mn2 | 128.2 (4) |
C5—N1—Mn1 | 114.6 (3) | C23—N5—Mn2 | 114.9 (4) |
C6—N2—C7 | 122.4 (5) | C24—N6—C25 | 121.7 (5) |
C6—N2—Mn1 | 119.7 (4) | C24—N6—Mn2 | 120.0 (4) |
C7—N2—Mn1 | 116.8 (4) | C25—N6—Mn2 | 118.3 (3) |
C13—N3—C12 | 124.0 (5) | C31—N7—C30 | 123.4 (5) |
C13—N3—Mn1 | 118.6 (4) | C31—N7—Mn2 | 118.6 (4) |
C12—N3—Mn1 | 117.4 (4) | C30—N7—Mn2 | 118.0 (3) |
C18—N4—C14 | 117.6 (5) | C36—N8—C32 | 117.2 (5) |
C18—N4—Mn1 | 128.0 (4) | C36—N8—Mn2 | 126.4 (4) |
C14—N4—Mn1 | 113.9 (3) | C32—N8—Mn2 | 116.2 (4) |
N1—C1—C2 | 122.9 (6) | N5—C19—C20 | 123.4 (6) |
N1—C1—H1 | 118.5 | N5—C19—H19 | 118.3 |
C2—C1—H1 | 118.5 | C20—C19—H19 | 118.3 |
C3—C2—C1 | 119.5 (6) | C21—C20—C19 | 119.8 (6) |
C3—C2—H2 | 120.3 | C21—C20—H20 | 120.1 |
C1—C2—H2 | 120.3 | C19—C20—H20 | 120.1 |
C2—C3—C4 | 118.6 (6) | C22—C21—C20 | 117.7 (6) |
C2—C3—H3 | 120.7 | C22—C21—H21 | 121.1 |
C4—C3—H3 | 120.7 | C20—C21—H21 | 121.1 |
C5—C4—C3 | 118.2 (6) | C21—C22—C23 | 119.7 (6) |
C5—C4—H4 | 120.9 | C21—C22—H22 | 120.2 |
C3—C4—H4 | 120.9 | C23—C22—H22 | 120.2 |
N1—C5—C4 | 124.0 (5) | N5—C23—C22 | 122.8 (5) |
N1—C5—C6 | 115.8 (5) | N5—C23—C24 | 116.1 (5) |
C4—C5—C6 | 120.2 (5) | C22—C23—C24 | 121.1 (5) |
N2—C6—C5 | 118.9 (5) | N6—C24—C23 | 119.7 (5) |
N2—C6—H6 | 120.5 | N6—C24—H24 | 120.1 |
C5—C6—H6 | 120.5 | C23—C24—H24 | 120.1 |
C12—C7—N2 | 109.7 (6) | N6—C25—C30 | 106.7 (4) |
C12—C7—C8 | 116.5 (6) | N6—C25—C26 | 116.5 (5) |
N2—C7—C8 | 115.7 (6) | C30—C25—C26 | 110.7 (5) |
C12—C7—H7 | 104.5 | N6—C25—H25 | 107.5 |
N2—C7—H7 | 104.5 | C30—C25—H25 | 107.5 |
C8—C7—H7 | 104.5 | C26—C25—H25 | 107.5 |
C9—C8—C7 | 110.9 (6) | C27—C26—C25 | 110.0 (6) |
C9—C8—H8A | 109.5 | C27—C26—H26A | 109.7 |
C7—C8—H8A | 109.5 | C25—C26—H26A | 109.7 |
C9—C8—H8B | 109.5 | C27—C26—H26B | 109.7 |
C7—C8—H8B | 109.5 | C25—C26—H26B | 109.7 |
H8A—C8—H8B | 108.1 | H26A—C26—H26B | 108.2 |
C10—C9—C8 | 117.2 (6) | C28—C27—C26 | 111.7 (6) |
C10—C9—H9A | 108.0 | C28—C27—H27A | 109.3 |
C8—C9—H9A | 108.0 | C26—C27—H27A | 109.3 |
C10—C9—H9B | 108.0 | C28—C27—H27B | 109.3 |
C8—C9—H9B | 108.0 | C26—C27—H27B | 109.3 |
H9A—C9—H9B | 107.2 | H27A—C27—H27B | 107.9 |
C9—C10—C11 | 117.2 (6) | C27—C28—C29 | 109.8 (6) |
C9—C10—H10A | 108.0 | C27—C28—H28A | 109.7 |
C11—C10—H10A | 108.0 | C29—C28—H28A | 109.7 |
C9—C10—H10B | 108.0 | C27—C28—H28B | 109.7 |
C11—C10—H10B | 108.0 | C29—C28—H28B | 109.7 |
H10A—C10—H10B | 107.2 | H28A—C28—H28B | 108.2 |
C10—C11—C12 | 111.9 (6) | C28—C29—C30 | 109.7 (6) |
C10—C11—H11A | 109.2 | C28—C29—H29A | 109.7 |
C12—C11—H11A | 109.2 | C30—C29—H29A | 109.7 |
C10—C11—H11B | 109.2 | C28—C29—H29B | 109.7 |
C12—C11—H11B | 109.2 | C30—C29—H29B | 109.7 |
H11A—C11—H11B | 107.9 | H29A—C29—H29B | 108.2 |
C7—C12—N3 | 111.6 (6) | N7—C30—C25 | 106.3 (4) |
C7—C12—C11 | 114.3 (6) | N7—C30—C29 | 115.4 (5) |
N3—C12—C11 | 118.8 (6) | C25—C30—C29 | 110.8 (5) |
C7—C12—H12 | 103.3 | N7—C30—H30 | 108.0 |
N3—C12—H12 | 103.3 | C25—C30—H30 | 108.0 |
C11—C12—H12 | 103.3 | C29—C30—H30 | 108.0 |
N3—C13—C14 | 119.0 (5) | N7—C31—C32 | 120.8 (5) |
N3—C13—H13 | 120.5 | N7—C31—H31 | 119.6 |
C14—C13—H13 | 120.5 | C32—C31—H31 | 119.6 |
N4—C14—C15 | 122.6 (5) | N8—C32—C33 | 123.0 (6) |
N4—C14—C13 | 116.1 (5) | N8—C32—C31 | 115.2 (5) |
C15—C14—C13 | 121.3 (5) | C33—C32—C31 | 121.9 (6) |
C16—C15—C14 | 119.2 (6) | C32—C33—C34 | 119.0 (6) |
C16—C15—H15 | 120.4 | C32—C33—H33 | 120.5 |
C14—C15—H15 | 120.4 | C34—C33—H33 | 120.5 |
C15—C16—C17 | 118.6 (6) | C35—C34—C33 | 118.9 (6) |
C15—C16—H16 | 120.7 | C35—C34—H34 | 120.6 |
C17—C16—H16 | 120.7 | C33—C34—H34 | 120.6 |
C16—C17—C18 | 118.9 (6) | C34—C35—C36 | 119.3 (7) |
C16—C17—H17 | 120.5 | C34—C35—H35 | 120.3 |
C18—C17—H17 | 120.5 | C36—C35—H35 | 120.3 |
N4—C18—C17 | 123.1 (6) | N8—C36—C35 | 122.5 (6) |
N4—C18—H18 | 118.4 | N8—C36—H36 | 118.7 |
C17—C18—H18 | 118.4 | C35—C36—H36 | 118.7 |
O1—Mn2—N6 | 87.55 (15) | Mn2—O1—H1W | 132.4 |
O1—Mn2—O2 | 75.62 (14) | Mn2—O1—H2W | 124.1 |
N6—Mn2—O2 | 145.34 (14) | H1W—O1—H2W | 103.6 |
O1—Mn2—N7 | 79.24 (15) | Mn2—O2—H3W | 130.0 |
N6—Mn2—N7 | 68.66 (17) | Mn2—O2—H4W | 118.0 |
O2—Mn2—N7 | 134.59 (16) | H3W—O2—H4W | 102.6 |
N3—Mn1—N1—C1 | 168.5 (4) | N8—Mn2—N5—C19 | −6.7 (7) |
N2—Mn1—N1—C1 | 174.0 (5) | Br3—Mn2—N5—C19 | −79.2 (5) |
N4—Mn1—N1—C1 | −17.5 (6) | O1—Mn2—N5—C23 | −91.6 (4) |
Br2—Mn1—N1—C1 | 60.1 (5) | N6—Mn2—N5—C23 | −1.7 (4) |
Br1—Mn1—N1—C1 | −92.4 (5) | O2—Mn2—N5—C23 | −168.2 (4) |
N3—Mn1—N1—C5 | −4.7 (5) | N7—Mn2—N5—C23 | −24.0 (5) |
N2—Mn1—N1—C5 | 0.8 (4) | N8—Mn2—N5—C23 | 166.8 (4) |
N4—Mn1—N1—C5 | 169.3 (3) | Br3—Mn2—N5—C23 | 94.3 (4) |
Br2—Mn1—N1—C5 | −113.1 (4) | O1—Mn2—N6—C24 | 84.1 (4) |
Br1—Mn1—N1—C5 | 94.4 (4) | O2—Mn2—N6—C24 | 24.1 (6) |
N3—Mn1—N2—C6 | 179.6 (5) | N7—Mn2—N6—C24 | 163.5 (5) |
N4—Mn1—N2—C6 | −166.2 (4) | N8—Mn2—N6—C24 | −173.2 (4) |
N1—Mn1—N2—C6 | 3.1 (5) | N5—Mn2—N6—C24 | 0.4 (4) |
Br2—Mn1—N2—C6 | 82.5 (5) | Br3—Mn2—N6—C24 | −86.3 (4) |
Br1—Mn1—N2—C6 | −81.0 (5) | O1—Mn2—N6—C25 | −96.3 (4) |
N3—Mn1—N2—C7 | −12.1 (5) | O2—Mn2—N6—C25 | −156.4 (3) |
N4—Mn1—N2—C7 | 2.1 (6) | N7—Mn2—N6—C25 | −16.9 (4) |
N1—Mn1—N2—C7 | 171.4 (5) | N8—Mn2—N6—C25 | 6.4 (5) |
Br2—Mn1—N2—C7 | −109.2 (5) | N5—Mn2—N6—C25 | 180.0 (4) |
Br1—Mn1—N2—C7 | 87.3 (5) | Br3—Mn2—N6—C25 | 93.3 (4) |
N2—Mn1—N3—C13 | 171.8 (5) | O1—Mn2—N7—C31 | −103.1 (4) |
N4—Mn1—N3—C13 | 0.8 (4) | N6—Mn2—N7—C31 | 165.3 (5) |
N1—Mn1—N3—C13 | 177.2 (4) | O2—Mn2—N7—C31 | −46.0 (5) |
Br2—Mn1—N3—C13 | −79.5 (4) | N8—Mn2—N7—C31 | 3.0 (4) |
Br1—Mn1—N3—C13 | 83.1 (4) | N5—Mn2—N7—C31 | −172.3 (4) |
N2—Mn1—N3—C12 | −10.2 (5) | Br3—Mn2—N7—C31 | 77.9 (4) |
N4—Mn1—N3—C12 | 178.8 (5) | O1—Mn2—N7—C30 | 77.8 (4) |
N1—Mn1—N3—C12 | −4.8 (6) | N6—Mn2—N7—C30 | −13.7 (4) |
Br2—Mn1—N3—C12 | 98.6 (5) | O2—Mn2—N7—C30 | 135.0 (4) |
Br1—Mn1—N3—C12 | −98.9 (5) | N8—Mn2—N7—C30 | −176.0 (4) |
N3—Mn1—N4—C18 | −175.0 (5) | N5—Mn2—N7—C30 | 8.7 (5) |
N2—Mn1—N4—C18 | 170.8 (4) | Br3—Mn2—N7—C30 | −101.1 (4) |
N1—Mn1—N4—C18 | 8.9 (6) | O1—Mn2—N8—C36 | −107.4 (5) |
Br2—Mn1—N4—C18 | −69.6 (5) | N6—Mn2—N8—C36 | 155.4 (4) |
Br1—Mn1—N4—C18 | 83.6 (5) | O2—Mn2—N8—C36 | −34.4 (5) |
N3—Mn1—N4—C14 | −3.9 (3) | N7—Mn2—N8—C36 | 178.7 (5) |
N2—Mn1—N4—C14 | −18.1 (5) | N5—Mn2—N8—C36 | −9.5 (7) |
N1—Mn1—N4—C14 | 180.0 (3) | Br3—Mn2—N8—C36 | 64.0 (5) |
Br2—Mn1—N4—C14 | 101.5 (3) | O1—Mn2—N8—C32 | 68.2 (4) |
Br1—Mn1—N4—C14 | −105.3 (3) | N6—Mn2—N8—C32 | −28.9 (5) |
C5—N1—C1—C2 | 1.3 (8) | O2—Mn2—N8—C32 | 141.2 (4) |
Mn1—N1—C1—C2 | −171.8 (4) | N7—Mn2—N8—C32 | −5.6 (4) |
N1—C1—C2—C3 | −2.3 (10) | N5—Mn2—N8—C32 | 166.1 (4) |
C1—C2—C3—C4 | 1.0 (9) | Br3—Mn2—N8—C32 | −120.4 (4) |
C2—C3—C4—C5 | 1.0 (9) | C23—N5—C19—C20 | −0.4 (8) |
C1—N1—C5—C4 | 0.9 (8) | Mn2—N5—C19—C20 | 173.0 (4) |
Mn1—N1—C5—C4 | 175.0 (4) | N5—C19—C20—C21 | 1.7 (9) |
C1—N1—C5—C6 | −178.0 (5) | C19—C20—C21—C22 | −0.8 (9) |
Mn1—N1—C5—C6 | −4.0 (6) | C20—C21—C22—C23 | −1.3 (8) |
C3—C4—C5—N1 | −2.1 (8) | C19—N5—C23—C22 | −1.7 (8) |
C3—C4—C5—C6 | 176.8 (5) | Mn2—N5—C23—C22 | −176.0 (4) |
C7—N2—C6—C5 | −174.0 (6) | C19—N5—C23—C24 | 177.0 (5) |
Mn1—N2—C6—C5 | −6.4 (7) | Mn2—N5—C23—C24 | 2.7 (6) |
N1—C5—C6—N2 | 6.9 (8) | C21—C22—C23—N5 | 2.6 (8) |
C4—C5—C6—N2 | −172.0 (6) | C21—C22—C23—C24 | −176.0 (5) |
C6—N2—C7—C12 | −159.9 (7) | C25—N6—C24—C23 | −178.7 (5) |
Mn1—N2—C7—C12 | 32.1 (9) | Mn2—N6—C24—C23 | 0.9 (7) |
C6—N2—C7—C8 | −25.6 (10) | N5—C23—C24—N6 | −2.5 (8) |
Mn1—N2—C7—C8 | 166.4 (5) | C22—C23—C24—N6 | 176.3 (5) |
C12—C7—C8—C9 | −44.1 (10) | C24—N6—C25—C30 | −137.7 (5) |
N2—C7—C8—C9 | −175.2 (7) | Mn2—N6—C25—C30 | 42.7 (5) |
C7—C8—C9—C10 | 40.7 (12) | C24—N6—C25—C26 | −13.6 (8) |
C8—C9—C10—C11 | −42.9 (13) | Mn2—N6—C25—C26 | 166.9 (4) |
C9—C10—C11—C12 | 43.4 (11) | N6—C25—C26—C27 | −178.6 (6) |
N2—C7—C12—N3 | −39.5 (10) | C30—C25—C26—C27 | −56.6 (7) |
C8—C7—C12—N3 | −173.4 (6) | C25—C26—C27—C28 | 58.7 (8) |
N2—C7—C12—C11 | −177.8 (6) | C26—C27—C28—C29 | −59.5 (8) |
C8—C7—C12—C11 | 48.3 (10) | C27—C28—C29—C30 | 57.6 (8) |
C13—N3—C12—C7 | −150.9 (7) | C31—N7—C30—C25 | −139.5 (5) |
Mn1—N3—C12—C7 | 31.2 (9) | Mn2—N7—C30—C25 | 39.5 (5) |
C13—N3—C12—C11 | −14.7 (10) | C31—N7—C30—C29 | −16.2 (8) |
Mn1—N3—C12—C11 | 167.4 (5) | Mn2—N7—C30—C29 | 162.7 (4) |
C10—C11—C12—C7 | −45.7 (10) | N6—C25—C30—N7 | −49.9 (5) |
C10—C11—C12—N3 | 179.1 (7) | C26—C25—C30—N7 | −177.6 (4) |
C12—N3—C13—C14 | −175.5 (6) | N6—C25—C30—C29 | −176.0 (5) |
Mn1—N3—C13—C14 | 2.4 (7) | C26—C25—C30—C29 | 56.3 (6) |
C18—N4—C14—C15 | 0.2 (8) | C28—C29—C30—N7 | −177.4 (5) |
Mn1—N4—C14—C15 | −171.8 (4) | C28—C29—C30—C25 | −56.6 (7) |
C18—N4—C14—C13 | 178.5 (5) | C30—N7—C31—C32 | 178.7 (5) |
Mn1—N4—C14—C13 | 6.4 (6) | Mn2—N7—C31—C32 | −0.3 (7) |
N3—C13—C14—N4 | −6.0 (7) | C36—N8—C32—C33 | 3.1 (8) |
N3—C13—C14—C15 | 172.2 (5) | Mn2—N8—C32—C33 | −172.9 (4) |
N4—C14—C15—C16 | −0.1 (8) | C36—N8—C32—C31 | −176.4 (5) |
C13—C14—C15—C16 | −178.2 (5) | Mn2—N8—C32—C31 | 7.5 (6) |
C14—C15—C16—C17 | 0.1 (8) | N7—C31—C32—N8 | −5.0 (8) |
C15—C16—C17—C18 | −0.2 (8) | N7—C31—C32—C33 | 175.4 (5) |
C14—N4—C18—C17 | −0.4 (8) | N8—C32—C33—C34 | −0.9 (9) |
Mn1—N4—C18—C17 | 170.4 (4) | C31—C32—C33—C34 | 178.7 (5) |
C16—C17—C18—N4 | 0.4 (9) | C32—C33—C34—C35 | −2.3 (9) |
O1—Mn2—N5—C19 | 94.9 (5) | C33—C34—C35—C36 | 3.1 (10) |
N6—Mn2—N5—C19 | −175.2 (5) | C32—N8—C36—C35 | −2.3 (8) |
O2—Mn2—N5—C19 | 18.3 (5) | Mn2—N8—C36—C35 | 173.4 (4) |
N7—Mn2—N5—C19 | 162.5 (4) | C34—C35—C36—N8 | −0.8 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1W···Br1i | 0.942 | 2.38 | 3.320 (4) | 172.3 |
O1—H2W···Br4ii | 0.855 | 2.46 | 3.291 (4) | 165.0 |
O2—H3W···Br4 | 0.907 | 2.53 | 3.413 (4) | 163.8 |
O2—H4W···Br4ii | 0.840 | 2.47 | 3.303 (4) | 169.2 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [MnBr(C18H20N4)(H2O)2]Br·[MnBr2(C18H20N4)] |
Mr | 1050.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 243 |
a, b, c (Å) | 11.8283 (9), 12.4842 (9), 14.134 (1) |
α, β, γ (°) | 97.971 (1), 91.017 (1), 98.036 (1) |
V (Å3) | 2045.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 4.57 |
Crystal size (mm) | 0.15 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.520, 0.633 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12149, 8169, 5661 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.137, 1.00 |
No. of reflections | 8169 |
No. of parameters | 469 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.85, −0.70 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1W···Br1i | 0.942 | 2.38 | 3.320 (4) | 172.3 |
O1—H2W···Br4ii | 0.855 | 2.46 | 3.291 (4) | 165.0 |
O2—H3W···Br4 | 0.907 | 2.53 | 3.413 (4) | 163.8 |
O2—H4W···Br4ii | 0.840 | 2.47 | 3.303 (4) | 169.2 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1. |
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The crystal structure of the title compound, [MnBr2(C18H20N4)][MnBr(C18H20N4)(H2O)2]Br, consists of two different MnII complexes in an asymmetric unit (Fig. 1). In one neutral complex, Mn2+ ion is six-coordinated in a distorted octahedral environment by four N atoms from the tetradentate ligand N,N'-bis(2-pyridylmethylidene)-1,2-diiminocyclohexane (bpic) occupying equatorial positions and two Br atoms occupying axial positions. Within the equatorial plane, the chelating angles lie in the range of 70.69 (16)–71.98 (16)°. The apical Br1—Mn1—Br2 bond angle is 151.60 (4)°. In the other cation complex, Mn2+ ion is seven-coordinated in an approximately pentagonal bipyramidal structure by four N atoms from bpic, one Br atom and two O atoms from water ligands. The four N atoms and one O atom occupy the equatorial positions, and the Br atom and one O atom lie in the axial positions. Within the equatorial plane, the chelating angles lie in the range of 68.66 (17)–69.23 (16)°. The apical Br3—Mn2—O1 bond angle is 170.10 (10)°. The compound displays intermolecular hydrogen bonds between the O atoms and the Br atoms (Br1, Br4) (Fig. 2). Moreover, there are intermolecular π–π interactions between the adjacent pyridine rings. The distances between Cg1 (the centroid of six-membered ring N1–C5) and Cg4iii [ring N8–C36; symmetry code: (iii) 1 - x, 1 - y, -z], and between Cg2 (ring N4–C18) and Cg3iv [ring N5–C23; symmetry code: (iv) 1 - x, 2 - y, 1 - z] are 3.604 Å and 3.680 Å, repectively, with the respective dihedral angles between the ring planes 4.7° and 5.0°.