Diaqua­[(1R,2R)-N,N′-bis­(3,5-dibromo­salicylidene)cyclo­hexa­ne-1,2-diamine-κ⁴O,N,N′,O′]manganese(III) perchlorate dihydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](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

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

Crystal data

[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) Å^3	0.60 × 0.30 × 0.20 mm
Z = 2

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 1.5653P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)