metal-organic compounds
The crystal structure of the title compound, [Mn(C20H16Br4N2O2)(H2O)2](ClO4)·2H2O, has been determined. The mononuclear complex affords an elongated octahedral MnN2O4 coordination geometry with the four donor atoms of the tetradentate chiral Schiff base in the equatorial plane and with two aqua ligands in axial positions with Mn—O = 2.278 (9) and 2.269 (10) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009062/sj6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009062/sj6054Isup2.hkl |
CCDC reference: 270544
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.016 Å
- H-atom completeness 67%
- R factor = 0.042
- wR factor = 0.122
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O9
Author Response: H atoms of the aqua ligands, O3 and O4, and solvents, O9 and O10, were not included, since they could not be observed in difference Fourier maps, nor located uniquely by considering hydrogen-bonding features. |
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O10
Author Response: H atoms of the aqua ligands, O3 and O4, and solvents, O9 and O10, were not included, since they could not be observed in difference Fourier maps, nor located uniquely by considering hydrogen-bonding features. |
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.246 0.307 Tmin and Tmax expected: 0.133 0.307 RR = 1.850 Please check that your absorption correction is appropriate. PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.00 Sigma PLAT060_ALERT_3_B Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.79 PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 16 PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. O9 .. 2.80 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O4 .. O10 .. 2.68 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O7 .. O10 .. 2.82 Ang.
Alert level C CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O8 .. 3.12 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br3 .. O3 .. 3.34 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. C18 .. 3.13 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H24 Br4 Cl1 Mn1 N2 O10 Atom count from the _atom_site data: C20 H16 Br4 Cl1 Mn1 N2 O10 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C20 H24 Br4 Cl Mn N2 O10 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 40.00 40.00 0.00 H 48.00 32.00 16.00 Br 8.00 8.00 0.00 Cl 2.00 2.00 0.00 Mn 2.00 2.00 0.00 N 4.00 4.00 0.00 O 20.00 20.00 0.00 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.56 From the CIF: _reflns_number_total 3620 Count of symmetry unique reflns 3628 Completeness (_total/calc) 99.78% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Diaqua[(1R,2R)-N,N'-bis(3,5-dibromosalicylidene)cyclohexane-1,2-diamine-
κ4O,N,N',O']manganese(III) perchlorate
dihydrate top
Crystal data top
[Mn(C20H16Br4N2O2)(H2O)2](ClO4)·2H2O | F(000) = 824 |
Mr = 854.34 | Dx = 1.893 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 13.270 (5) Å | θ = 10.0–11.5° |
b = 11.612 (5) Å | µ = 5.91 mm−1 |
c = 10.530 (6) Å | T = 297 K |
β = 112.48 (3)° | Prism, brown |
V = 1499.3 (13) Å3 | 0.60 × 0.30 × 0.20 mm |
Z = 2 |
Data collection top
Rigaku AFC-7R diffractometer | 2220 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating-anode generator | Rint = 0.000 |
Graphite monochromator | θmax = 27.6°, θmin = 2.7° |
ω–2θ scans | h = 0→17 |
Absorption correction: ψ scans (North et al., 1968) | k = 0→15 |
Tmin = 0.246, Tmax = 0.307 | l = −13→12 |
3620 measured reflections | 3 standard reflections every 150 reflections |
3620 independent reflections | intensity decay: 1.5% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0574P)2 + 1.5653P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.57 e Å−3 |
3620 reflections | Δρmin = −0.48 e Å−3 |
344 parameters | Extinction correction: SHELXL97 |
1 restraint | Extinction coefficient: 0.0006 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.02 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.61145 (9) | 0.29033 (12) | 0.79728 (12) | 0.0650 (4) | |
Br2 | 0.37427 (12) | 0.12004 (13) | 1.10154 (13) | 0.0753 (4) | |
Br3 | 0.27669 (11) | 0.57468 (12) | −0.24055 (12) | 0.0669 (4) | |
Br4 | 0.56602 (9) | 0.40042 (16) | 0.26340 (15) | 0.0857 (5) | |
Mn1 | 0.26958 (10) | 0.36269 (14) | 0.41721 (15) | 0.0429 (4) | |
Cl1 | 0.0604 (3) | 0.7457 (3) | 0.1910 (4) | 0.0717 (9) | |
O1 | 0.3846 (5) | 0.3377 (7) | 0.5880 (6) | 0.0514 (18) | |
O2 | 0.3609 (5) | 0.3713 (8) | 0.3165 (7) | 0.0550 (19) | |
O3 | 0.2860 (6) | 0.5570 (8) | 0.4478 (8) | 0.066 (2) | |
O4 | 0.2652 (8) | 0.1682 (8) | 0.3959 (10) | 0.082 (3) | |
O5 | 0.056 (2) | 0.6842 (15) | 0.2980 (17) | 0.227 (12) | |
O6 | 0.013 (2) | 0.8478 (19) | 0.1928 (17) | 0.217 (11) | |
O7 | 0.012 (3) | 0.6968 (17) | 0.0648 (16) | 0.257 (14) | |
O8 | 0.1584 (15) | 0.762 (4) | 0.215 (3) | 0.38 (3) | |
O9 | 0.5078 (14) | 0.1607 (19) | 0.4647 (15) | 0.184 (8) | |
O10 | 0.0973 (14) | 0.0794 (15) | 0.1843 (17) | 0.157 (6) | |
N1 | 0.1600 (6) | 0.3546 (8) | 0.5016 (8) | 0.0463 (19) | |
N2 | 0.1372 (6) | 0.3859 (7) | 0.2486 (8) | 0.0412 (18) | |
C1 | 0.3792 (7) | 0.2927 (10) | 0.6997 (10) | 0.043 (2) | |
C2 | 0.4753 (8) | 0.2633 (9) | 0.8110 (10) | 0.047 (2) | |
C3 | 0.4752 (9) | 0.2167 (10) | 0.9316 (10) | 0.052 (3) | |
H3 | 0.5405 | 0.2017 | 1.0049 | 0.063* | |
C4 | 0.3761 (9) | 0.1927 (9) | 0.9418 (10) | 0.049 (3) | |
C5 | 0.2791 (9) | 0.2182 (10) | 0.8375 (11) | 0.054 (3) | |
H5 | 0.2135 | 0.2014 | 0.8460 | 0.065* | |
C6 | 0.2799 (7) | 0.2699 (9) | 0.7177 (10) | 0.041 (2) | |
C7 | 0.1768 (8) | 0.3078 (10) | 0.6191 (10) | 0.049 (3) | |
H7 | 0.1163 | 0.2978 | 0.6421 | 0.058* | |
C8 | 0.0541 (7) | 0.4021 (11) | 0.4129 (10) | 0.055 (3) | |
H8 | 0.0620 | 0.4861 | 0.4140 | 0.066* | |
C9 | −0.0433 (8) | 0.3754 (17) | 0.4535 (13) | 0.088 (5) | |
H9A | −0.0522 | 0.2927 | 0.4577 | 0.107* | |
H9B | −0.0305 | 0.4075 | 0.5434 | 0.107* | |
C10 | −0.1450 (9) | 0.428 (2) | 0.3471 (15) | 0.120 (9) | |
H10A | −0.2073 | 0.4071 | 0.3692 | 0.146* | |
H10B | −0.1383 | 0.5109 | 0.3517 | 0.146* | |
C11 | −0.1654 (9) | 0.3899 (19) | 0.2058 (16) | 0.102 (6) | |
H11A | −0.2290 | 0.4299 | 0.1427 | 0.123* | |
H11B | −0.1816 | 0.3082 | 0.1981 | 0.123* | |
C12 | −0.0698 (7) | 0.4121 (14) | 0.1637 (12) | 0.071 (4) | |
H12A | −0.0838 | 0.3772 | 0.0749 | 0.085* | |
H12B | −0.0607 | 0.4943 | 0.1558 | 0.085* | |
C13 | 0.0318 (7) | 0.3625 (10) | 0.2684 (10) | 0.049 (2) | |
H13 | 0.0222 | 0.2787 | 0.2668 | 0.059* | |
C14 | 0.1361 (8) | 0.4245 (10) | 0.1330 (10) | 0.047 (2) | |
H14 | 0.0685 | 0.4402 | 0.0645 | 0.056* | |
C15 | 0.2319 (7) | 0.4455 (10) | 0.1013 (10) | 0.046 (2) | |
C16 | 0.2125 (9) | 0.4946 (10) | −0.0276 (10) | 0.050 (3) | |
H16 | 0.1424 | 0.5155 | −0.0858 | 0.060* | |
C17 | 0.2997 (9) | 0.5114 (10) | −0.0662 (11) | 0.051 (3) | |
C18 | 0.4045 (9) | 0.4786 (10) | 0.0173 (11) | 0.052 (3) | |
H18 | 0.4615 | 0.4847 | −0.0131 | 0.062* | |
C19 | 0.4225 (8) | 0.4365 (10) | 0.1473 (11) | 0.052 (3) | |
C20 | 0.3376 (8) | 0.4186 (10) | 0.1930 (10) | 0.045 (2) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0407 (5) | 0.0847 (9) | 0.0635 (7) | 0.0068 (6) | 0.0133 (5) | 0.0052 (7) |
Br2 | 0.0949 (10) | 0.0769 (9) | 0.0591 (7) | 0.0160 (8) | 0.0350 (7) | 0.0234 (7) |
Br3 | 0.0902 (9) | 0.0619 (8) | 0.0560 (6) | −0.0087 (7) | 0.0362 (6) | 0.0044 (6) |
Br4 | 0.0396 (5) | 0.1338 (15) | 0.0862 (9) | 0.0024 (8) | 0.0270 (6) | 0.0149 (9) |
Mn1 | 0.0310 (6) | 0.0544 (10) | 0.0440 (7) | 0.0013 (7) | 0.0150 (6) | 0.0069 (7) |
Cl1 | 0.0703 (18) | 0.067 (2) | 0.081 (2) | 0.0189 (17) | 0.0327 (16) | 0.0082 (17) |
O1 | 0.038 (3) | 0.070 (5) | 0.044 (4) | 0.006 (3) | 0.014 (3) | 0.015 (3) |
O2 | 0.035 (3) | 0.079 (5) | 0.052 (4) | 0.004 (4) | 0.018 (3) | 0.007 (4) |
O3 | 0.059 (5) | 0.066 (6) | 0.072 (5) | 0.003 (4) | 0.024 (4) | 0.007 (4) |
O4 | 0.092 (7) | 0.063 (6) | 0.095 (7) | −0.004 (5) | 0.043 (6) | −0.008 (5) |
O5 | 0.47 (4) | 0.109 (12) | 0.115 (12) | 0.017 (17) | 0.123 (17) | 0.022 (10) |
O6 | 0.31 (3) | 0.193 (18) | 0.134 (13) | 0.166 (19) | 0.075 (15) | 0.042 (13) |
O7 | 0.51 (4) | 0.133 (14) | 0.090 (10) | −0.06 (2) | 0.079 (17) | −0.028 (10) |
O8 | 0.115 (14) | 0.71 (8) | 0.38 (4) | −0.01 (3) | 0.16 (2) | 0.02 (5) |
O9 | 0.149 (12) | 0.27 (2) | 0.119 (11) | 0.116 (15) | 0.037 (9) | 0.035 (13) |
O10 | 0.166 (13) | 0.111 (11) | 0.161 (13) | −0.021 (11) | 0.028 (11) | −0.011 (11) |
N1 | 0.033 (4) | 0.056 (5) | 0.047 (4) | 0.009 (4) | 0.012 (3) | 0.006 (4) |
N2 | 0.031 (3) | 0.045 (5) | 0.048 (4) | −0.001 (4) | 0.015 (3) | −0.001 (4) |
C1 | 0.038 (4) | 0.045 (6) | 0.044 (5) | 0.004 (5) | 0.015 (4) | −0.001 (5) |
C2 | 0.041 (5) | 0.047 (7) | 0.050 (5) | 0.004 (5) | 0.012 (4) | 0.000 (5) |
C3 | 0.057 (6) | 0.050 (7) | 0.047 (6) | 0.018 (5) | 0.017 (5) | 0.013 (5) |
C4 | 0.066 (7) | 0.040 (6) | 0.039 (5) | 0.015 (5) | 0.018 (5) | 0.007 (5) |
C5 | 0.066 (7) | 0.054 (7) | 0.051 (6) | 0.005 (6) | 0.031 (5) | 0.001 (5) |
C6 | 0.039 (4) | 0.039 (6) | 0.051 (5) | 0.009 (4) | 0.023 (4) | 0.004 (5) |
C7 | 0.042 (5) | 0.058 (7) | 0.052 (6) | 0.006 (5) | 0.026 (4) | 0.010 (5) |
C8 | 0.031 (4) | 0.075 (8) | 0.057 (6) | −0.001 (5) | 0.014 (4) | 0.023 (6) |
C9 | 0.046 (6) | 0.157 (15) | 0.074 (8) | 0.005 (9) | 0.037 (6) | 0.040 (10) |
C10 | 0.038 (6) | 0.24 (3) | 0.085 (10) | 0.031 (10) | 0.031 (6) | 0.075 (14) |
C11 | 0.039 (6) | 0.168 (18) | 0.094 (10) | −0.004 (9) | 0.018 (6) | 0.047 (12) |
C12 | 0.030 (5) | 0.112 (11) | 0.059 (6) | −0.007 (6) | 0.005 (4) | 0.008 (7) |
C13 | 0.034 (4) | 0.051 (6) | 0.052 (6) | −0.007 (5) | 0.006 (4) | 0.009 (5) |
C14 | 0.038 (5) | 0.058 (7) | 0.039 (5) | 0.000 (5) | 0.009 (4) | −0.002 (5) |
C15 | 0.037 (5) | 0.048 (6) | 0.055 (6) | −0.002 (4) | 0.020 (4) | −0.007 (5) |
C16 | 0.051 (6) | 0.050 (7) | 0.044 (5) | −0.001 (5) | 0.013 (5) | −0.009 (5) |
C17 | 0.057 (6) | 0.050 (6) | 0.050 (6) | −0.013 (5) | 0.025 (5) | −0.006 (5) |
C18 | 0.052 (6) | 0.054 (7) | 0.054 (6) | −0.011 (5) | 0.024 (5) | −0.003 (5) |
C19 | 0.039 (5) | 0.063 (7) | 0.057 (6) | −0.004 (5) | 0.021 (5) | −0.002 (6) |
C20 | 0.039 (5) | 0.050 (6) | 0.044 (5) | −0.003 (5) | 0.015 (4) | −0.005 (5) |
Geometric parameters (Å, º) top
Br1—C2 | 1.893 (10) | C6—C7 | 1.435 (14) |
Br2—C4 | 1.891 (10) | C7—H7 | 0.9300 |
Br3—C17 | 1.891 (11) | C8—C13 | 1.506 (15) |
Br4—C19 | 1.875 (10) | C8—C9 | 1.540 (13) |
Mn1—O1 | 1.884 (6) | C8—H8 | 0.9800 |
Mn1—O2 | 1.893 (6) | C9—C10 | 1.513 (18) |
Mn1—N1 | 1.975 (8) | C9—H9A | 0.9700 |
Mn1—N2 | 1.981 (8) | C9—H9B | 0.9700 |
Mn1—O4 | 2.269 (10) | C10—C11 | 1.47 (2) |
Mn1—O3 | 2.278 (9) | C10—H10A | 0.9700 |
Cl1—O8 | 1.241 (17) | C10—H10B | 0.9700 |
Cl1—O6 | 1.348 (16) | C11—C12 | 1.518 (16) |
Cl1—O5 | 1.355 (17) | C11—H11A | 0.9700 |
Cl1—O7 | 1.360 (16) | C11—H11B | 0.9700 |
O1—C1 | 1.314 (11) | C12—C13 | 1.492 (14) |
O2—C20 | 1.335 (12) | C12—H12A | 0.9700 |
N1—C7 | 1.290 (12) | C12—H12B | 0.9700 |
N1—C8 | 1.466 (12) | C13—H13 | 0.9800 |
N2—C14 | 1.293 (13) | C14—C15 | 1.452 (13) |
N2—C13 | 1.516 (12) | C14—H14 | 0.9300 |
C1—C2 | 1.405 (13) | C15—C20 | 1.401 (13) |
C1—C6 | 1.425 (13) | C15—C16 | 1.403 (15) |
C2—C3 | 1.381 (14) | C16—C17 | 1.378 (14) |
C3—C4 | 1.388 (15) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.385 (16) |
C4—C5 | 1.367 (15) | C18—C19 | 1.385 (15) |
C5—C6 | 1.401 (14) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.399 (14) |
O1—Mn1—O2 | 94.8 (3) | C13—C8—H8 | 107.2 |
O1—Mn1—N1 | 91.7 (3) | C9—C8—H8 | 107.2 |
O2—Mn1—N1 | 173.4 (3) | C10—C9—C8 | 108.6 (10) |
O1—Mn1—N2 | 173.5 (3) | C10—C9—H9A | 110.0 |
O2—Mn1—N2 | 91.6 (3) | C8—C9—H9A | 110.0 |
N1—Mn1—N2 | 81.8 (3) | C10—C9—H9B | 110.0 |
O1—Mn1—O4 | 85.5 (4) | C8—C9—H9B | 110.0 |
O2—Mn1—O4 | 89.7 (4) | H9A—C9—H9B | 108.3 |
N1—Mn1—O4 | 90.1 (4) | C11—C10—C9 | 113.3 (15) |
N2—Mn1—O4 | 93.8 (4) | C11—C10—H10A | 108.9 |
O1—Mn1—O3 | 91.1 (3) | C9—C10—H10A | 108.9 |
O2—Mn1—O3 | 88.8 (3) | C11—C10—H10B | 108.9 |
N1—Mn1—O3 | 91.8 (4) | C9—C10—H10B | 108.9 |
N2—Mn1—O3 | 89.8 (3) | H10A—C10—H10B | 107.7 |
O4—Mn1—O3 | 176.2 (3) | C10—C11—C12 | 113.1 (12) |
O8—Cl1—O6 | 109 (2) | C10—C11—H11A | 109.0 |
O8—Cl1—O5 | 107 (2) | C12—C11—H11A | 109.0 |
O6—Cl1—O5 | 106.3 (13) | C10—C11—H11B | 109.0 |
O8—Cl1—O7 | 109.4 (19) | C12—C11—H11B | 109.0 |
O6—Cl1—O7 | 109.4 (14) | H11A—C11—H11B | 107.8 |
O5—Cl1—O7 | 116.0 (12) | C13—C12—C11 | 109.8 (10) |
C1—O1—Mn1 | 127.9 (6) | C13—C12—H12A | 109.7 |
C20—O2—Mn1 | 127.5 (6) | C11—C12—H12A | 109.7 |
C7—N1—C8 | 122.8 (8) | C13—C12—H12B | 109.7 |
C7—N1—Mn1 | 124.4 (6) | C11—C12—H12B | 109.7 |
C8—N1—Mn1 | 112.7 (6) | H12A—C12—H12B | 108.2 |
C14—N2—C13 | 120.9 (7) | C12—C13—C8 | 113.7 (10) |
C14—N2—Mn1 | 125.3 (6) | C12—C13—N2 | 116.7 (9) |
C13—N2—Mn1 | 113.6 (6) | C8—C13—N2 | 104.4 (7) |
O1—C1—C2 | 120.0 (8) | C12—C13—H13 | 107.2 |
O1—C1—C6 | 124.3 (8) | C8—C13—H13 | 107.2 |
C2—C1—C6 | 115.8 (9) | N2—C13—H13 | 107.2 |
C3—C2—C1 | 122.8 (9) | N2—C14—C15 | 125.4 (9) |
C3—C2—Br1 | 118.2 (7) | N2—C14—H14 | 117.3 |
C1—C2—Br1 | 119.0 (8) | C15—C14—H14 | 117.3 |
C2—C3—C4 | 118.9 (9) | C20—C15—C16 | 121.5 (9) |
C2—C3—H3 | 120.5 | C20—C15—C14 | 122.5 (9) |
C4—C3—H3 | 120.5 | C16—C15—C14 | 116.0 (9) |
C5—C4—C3 | 121.6 (9) | C17—C16—C15 | 118.6 (10) |
C5—C4—Br2 | 118.9 (9) | C17—C16—H16 | 120.7 |
C3—C4—Br2 | 119.5 (7) | C15—C16—H16 | 120.7 |
C4—C5—C6 | 119.2 (10) | C16—C17—C18 | 121.7 (10) |
C4—C5—H5 | 120.4 | C16—C17—Br3 | 120.0 (8) |
C6—C5—H5 | 120.4 | C18—C17—Br3 | 118.2 (8) |
C5—C6—C1 | 121.7 (9) | C19—C18—C17 | 118.4 (10) |
C5—C6—C7 | 116.7 (9) | C19—C18—H18 | 120.8 |
C1—C6—C7 | 121.4 (9) | C17—C18—H18 | 120.8 |
N1—C7—C6 | 126.2 (9) | C18—C19—C20 | 122.3 (10) |
N1—C7—H7 | 116.9 | C18—C19—Br4 | 118.1 (7) |
C6—C7—H7 | 116.9 | C20—C19—Br4 | 119.5 (8) |
N1—C8—C13 | 107.4 (8) | O2—C20—C19 | 118.6 (9) |
N1—C8—C9 | 116.7 (9) | O2—C20—C15 | 124.1 (8) |
C13—C8—C9 | 110.9 (9) | C19—C20—C15 | 117.1 (9) |
N1—C8—H8 | 107.2 | ||
Br1—C2—C1—O1 | 0 (1) | N1—Mn1—O1—C1 | 19.8 (9) |
Br1—C2—C1—C6 | −179.9 (8) | N1—Mn1—N2—C13 | −11.0 (7) |
Br1—C2—C3—C4 | −177.9 (8) | N1—Mn1—N2—C14 | 164.5 (10) |
Br2—C4—C3—C2 | 176.0 (8) | N1—C7—C6—C1 | 6 (1) |
Br2—C4—C5—C6 | −178.7 (8) | N1—C7—C6—C5 | −178 (1) |
Br3—C17—C16—C15 | 178.8 (8) | N1—C8—C9—C10 | −177 (1) |
Br3—C17—C18—C19 | 177.5 (9) | N1—C8—C13—N2 | −47 (1) |
Br4—C19—C18—C17 | −176.5 (9) | N1—C8—C13—C12 | −175 (1) |
Br4—C19—C20—O2 | −2 (1) | N2—Mn1—O2—C20 | 20.7 (9) |
Br4—C19—C20—C15 | −179.1 (8) | N2—Mn1—N1—C7 | 159.8 (10) |
Mn1—O1—C1—C2 | 169.7 (8) | N2—Mn1—N1—C8 | −17.1 (7) |
Mn1—O1—C1—C6 | −10 (1) | N2—C13—C8—C9 | −175 (1) |
Mn1—O2—C20—C15 | −16 (1) | N2—C13—C12—C11 | −174 (1) |
Mn1—O2—C20—C19 | 167.6 (8) | N2—C14—C15—C16 | −176 (1) |
Mn1—N1—C7—C6 | 10 (1) | N2—C14—C15—C20 | 3 (1) |
Mn1—N1—C8—C9 | 166.5 (10) | C1—C2—C3—C4 | 3 (1) |
Mn1—N1—C8—C13 | 41 (1) | C1—C6—C5—C4 | 2 (1) |
Mn1—N2—C13—C8 | 34 (1) | C2—C1—C6—C5 | −1 (1) |
Mn1—N2—C13—C12 | 161.3 (9) | C2—C1—C6—C7 | 172 (1) |
Mn1—N2—C14—C15 | 7 (1) | C2—C3—C4—C5 | −2 (1) |
O1—Mn1—O2—C20 | −160.1 (9) | C3—C2—C1—C6 | 0 (1) |
O1—Mn1—N1—C7 | −19.6 (9) | C3—C4—C5—C6 | 0 (1) |
O1—Mn1—N1—C8 | 163.6 (8) | C4—C5—C6—C7 | −172 (1) |
O1—C1—C2—C3 | 179 (1) | C6—C7—N1—C8 | −173 (1) |
O1—C1—C6—C5 | 177 (1) | C7—N1—C8—C9 | −10 (1) |
O1—C1—C6—C7 | −7 (1) | C7—N1—C8—C13 | −135 (1) |
O2—Mn1—O1—C1 | −159.5 (9) | C8—C9—C10—C11 | 55 (2) |
O2—Mn1—N2—C13 | 168.3 (7) | C8—C13—N2—C14 | −140 (1) |
O2—Mn1—N2—C14 | −16.1 (9) | C8—C13—C12—C11 | −53 (1) |
O2—C20—C15—C14 | 0 (1) | C9—C8—C13—C12 | 56 (1) |
O2—C20—C15—C16 | −179 (1) | C9—C10—C11—C12 | −55 (2) |
O2—C20—C19—C18 | 176 (1) | C10—C9—C8—C13 | −54 (1) |
O3—Mn1—O1—C1 | 111.6 (9) | C10—C11—C12—C13 | 52 (2) |
O3—Mn1—O2—C20 | −69.1 (9) | C12—C13—N2—C14 | −14 (1) |
O3—Mn1—N1—C7 | −110.7 (9) | C13—N2—C14—C15 | −177 (1) |
O3—Mn1—N1—C8 | 72.4 (8) | C14—C15—C16—C17 | −176 (1) |
O3—Mn1—N2—C13 | −102.8 (7) | C14—C15—C20—C19 | 176 (1) |
O3—Mn1—N2—C14 | 72.7 (9) | C15—C16—C17—C18 | 1 (1) |
O4—Mn1—O1—C1 | −70.2 (9) | C15—C20—C19—C18 | 0 (1) |
O4—Mn1—O2—C20 | 114.5 (9) | C16—C15—C20—C19 | −3 (1) |
O4—Mn1—N1—C7 | 65.9 (9) | C16—C17—C18—C19 | −5 (1) |
O4—Mn1—N1—C8 | −110.9 (8) | C17—C16—C15—C20 | 3 (1) |
O4—Mn1—N2—C13 | 78.6 (8) | C17—C18—C19—C20 | 4 (1) |
O4—Mn1—N2—C14 | −105.9 (9) | C17—C18—C19—C20 | 4 (1) |