Aqua­[N,N′-ethyl­ene­bis(5-nitro­salicylidene­iminato)]­methanol­manganese(III) perchlorate

The title compound, [Mn(C₁₆H₁₂N₄O₆)(CH₄O)(H₂O)]ClO₄, arose as an unexpected oxidation product, and contains an Mn^III cation coordinated by an equatorial salen-type ligand and Jahn–Teller-distorted axially coordinated water and methanol mol­ecules. A network of O—H...O and O—H...N hydrogen bonds helps to establish the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.146
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.82(3), Rep    0.820(5) ......       6.00 su-Rat
              O1W  -H1W2    1.555   1.555
PLAT732_ALERT_1_B Angle   Calc      110(4), Rep    110.2(9) ......       4.44 su-Rat
              H1W1 -O1W  -H1W2    1.555   1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.82(3), Rep    0.820(5) ......       6.00 su-Rat
              O1W  -H2#     1.555   1.555

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.837     0.947
            Tmin and Tmax expected:      0.747     0.947
            RR =      1.120
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.13
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         Cl
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            O1W -MN  -O1M -C1M  -109.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            O1B -MN  -N1A -C7A   177.00  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            O1A -MN  -N1B -C7B   173.50  0.70   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         17
PLAT731_ALERT_1_C Bond    Calc     0.82(2), Rep    0.818(5) ......       4.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(2), Rep    0.818(5) ......       4.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.11(3), Rep   2.105(14) ......       2.14 su-Rat
              H1#  -O52B    1.555   1.565
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl O4

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   6 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua[N,N'-ethylenebis(5-nitrosalicylideneiminato)]methanolmanganese(III) perchlorate

Crystal data

[Mn(C16H12N4O6)(CH4O)(H2O)]ClO4	Z = 2
Mr = 560.74	F(000) = 572
Triclinic, P1	Dx = 1.657 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3102 (15) Å	Cell parameters from 36 reflections
b = 10.3320 (16) Å	θ = 2.5–11.4°
c = 13.995 (2) Å	µ = 0.78 mm^−1
α = 84.549 (13)°	T = 293 K
β = 79.701 (15)°	Plate, pale brown
γ = 72.128 (12)°	0.49 × 0.32 × 0.07 mm
V = 1124.2 (3) Å^3

Data collection

Siemens P4S diffractometer	3452 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
2θ/ω scans	h = −10→0
Absorption correction: ψ scan (North et al., 1968)	k = −13→12
Tmin = 0.837, Tmax = 0.947	l = −18→17
5181 measured reflections	3 standard reflections every 97 reflections
5169 independent reflections	intensity decay: 0.01%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.3336P] where P = (Fo^2 + 2Fc^2)/3
5169 reflections	(Δ/σ)max = 0.023
324 parameters	Δρmax = 0.45 e Å^−3
4 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mn	0.12669 (7)	0.24444 (5)	0.26710 (4)	0.03583 (16)
Cl	−0.29676 (13)	0.25177 (11)	0.04343 (7)	0.0549 (3)
O11A	−0.2816 (7)	0.1147 (4)	0.0725 (3)	0.1263 (17)
O12A	−0.3641 (5)	0.3297 (5)	0.1266 (3)	0.1171 (16)
O13A	−0.4084 (5)	0.2944 (5)	−0.0245 (3)	0.1071 (15)
O14A	−0.1339 (4)	0.2635 (5)	0.0023 (3)	0.1000 (13)
O1A	0.1237 (3)	0.3581 (2)	0.36624 (17)	0.0437 (6)
O1B	0.0515 (3)	0.1093 (2)	0.35038 (17)	0.0426 (6)
O1M	0.3991 (4)	0.1309 (3)	0.2782 (2)	0.0608 (8)
H1M	0.4080	0.0496	0.2785	0.091*
O1W	−0.1522 (3)	0.3528 (3)	0.2586 (2)	0.0576 (7)
H1W1	−0.169 (5)	0.4327 (14)	0.269 (4)	0.086*
H1W2	−0.237 (3)	0.343 (4)	0.242 (4)	0.086*
O51A	0.3951 (5)	0.8342 (3)	0.4380 (3)	0.0805 (10)
O52A	0.4334 (4)	0.8450 (3)	0.2809 (2)	0.0629 (8)
O51B	−0.1670 (5)	−0.3357 (3)	0.1785 (2)	0.0741 (10)
O52B	−0.2365 (4)	−0.3765 (3)	0.3314 (2)	0.0591 (8)
N1A	0.1967 (4)	0.3741 (3)	0.1655 (2)	0.0378 (6)
N1B	0.1518 (4)	0.1390 (3)	0.1513 (2)	0.0399 (7)
N5A	0.3891 (4)	0.7926 (3)	0.3607 (3)	0.0548 (9)
N5B	−0.1797 (4)	−0.3093 (3)	0.2628 (3)	0.0472 (8)
C1A	0.2560 (4)	0.5162 (3)	0.2725 (3)	0.0377 (8)
C2A	0.1936 (4)	0.4578 (3)	0.3617 (3)	0.0392 (8)
C3A	0.2029 (5)	0.5099 (4)	0.4484 (3)	0.0513 (10)
H3AA	0.1646	0.4709	0.5073	0.062*
C4A	0.2673 (5)	0.6175 (4)	0.4490 (3)	0.0523 (10)
H4AA	0.2711	0.6515	0.5074	0.063*
C5A	0.3268 (5)	0.6750 (4)	0.3607 (3)	0.0464 (9)
C6A	0.3240 (5)	0.6254 (3)	0.2740 (3)	0.0416 (8)
H6AA	0.3670	0.6636	0.2159	0.050*
C7A	0.2505 (4)	0.4735 (3)	0.1793 (3)	0.0394 (8)
H7AA	0.2887	0.5212	0.1247	0.047*
C8A	0.1869 (5)	0.3430 (4)	0.0659 (3)	0.0479 (9)
H8AA	0.2619	0.3813	0.0184	0.058*
H8AB	0.0708	0.3810	0.0524	0.058*
C1B	0.0112 (4)	−0.0237 (3)	0.2302 (2)	0.0368 (7)
C2B	−0.0058 (4)	0.0134 (3)	0.3268 (2)	0.0369 (7)
C3B	−0.0846 (5)	−0.0596 (4)	0.4023 (3)	0.0442 (8)
H3BA	−0.0972	−0.0367	0.4665	0.053*
C4B	−0.1423 (5)	−0.1631 (4)	0.3823 (3)	0.0440 (8)
H4BA	−0.1925	−0.2108	0.4324	0.053*
C5B	−0.1250 (4)	−0.1963 (3)	0.2860 (3)	0.0401 (8)
C6B	−0.0506 (5)	−0.1294 (3)	0.2116 (3)	0.0415 (8)
H6BA	−0.0405	−0.1537	0.1479	0.050*
C7B	0.0950 (5)	0.0379 (4)	0.1482 (3)	0.0414 (8)
H7BA	0.1091	0.0014	0.0880	0.050*
C8B	0.2421 (5)	0.1904 (4)	0.0615 (3)	0.0487 (9)
H8BA	0.2111	0.1637	0.0044	0.058*
H8BB	0.3652	0.1540	0.0588	0.058*
C1M	0.5077 (8)	0.1502 (6)	0.3363 (5)	0.102 (2)
H1MA	0.6238	0.1201	0.3036	0.152*
H1MB	0.4966	0.0988	0.3967	0.152*
H1MC	0.4779	0.2451	0.3489	0.152*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn	0.0452 (3)	0.0325 (3)	0.0352 (3)	−0.0201 (2)	−0.0057 (2)	−0.0003 (2)
Cl	0.0525 (6)	0.0666 (7)	0.0466 (6)	−0.0197 (5)	−0.0081 (4)	−0.0010 (5)
O11A	0.178 (5)	0.074 (3)	0.117 (4)	−0.024 (3)	−0.033 (3)	0.017 (2)
O12A	0.086 (3)	0.147 (4)	0.113 (3)	−0.014 (3)	−0.003 (2)	−0.072 (3)
O13A	0.092 (3)	0.167 (4)	0.089 (3)	−0.077 (3)	−0.050 (2)	0.056 (3)
O14A	0.058 (2)	0.168 (4)	0.082 (3)	−0.045 (2)	−0.0004 (18)	−0.021 (3)
O1A	0.0562 (16)	0.0422 (13)	0.0402 (13)	−0.0279 (12)	−0.0027 (11)	−0.0038 (10)
O1B	0.0619 (16)	0.0394 (13)	0.0364 (13)	−0.0284 (12)	−0.0099 (11)	−0.0011 (10)
O1M	0.0549 (17)	0.0520 (17)	0.079 (2)	−0.0131 (14)	−0.0237 (15)	−0.0046 (15)
O1W	0.0494 (17)	0.0429 (15)	0.085 (2)	−0.0138 (13)	−0.0175 (15)	−0.0106 (15)
O51A	0.109 (3)	0.075 (2)	0.082 (2)	−0.057 (2)	−0.010 (2)	−0.0262 (18)
O52A	0.075 (2)	0.0443 (15)	0.079 (2)	−0.0336 (15)	−0.0085 (16)	−0.0012 (15)
O51B	0.118 (3)	0.070 (2)	0.0542 (19)	−0.059 (2)	−0.0028 (18)	−0.0179 (16)
O52B	0.077 (2)	0.0438 (15)	0.0672 (19)	−0.0357 (15)	−0.0137 (15)	0.0083 (13)
N1A	0.0425 (16)	0.0380 (15)	0.0372 (15)	−0.0191 (13)	−0.0062 (12)	0.0017 (12)
N1B	0.0477 (17)	0.0402 (16)	0.0357 (15)	−0.0207 (13)	−0.0022 (13)	−0.0033 (12)
N5A	0.058 (2)	0.0392 (18)	0.075 (3)	−0.0207 (16)	−0.0147 (18)	−0.0091 (17)
N5B	0.0519 (19)	0.0351 (16)	0.060 (2)	−0.0188 (14)	−0.0114 (16)	−0.0013 (15)
C1A	0.0381 (19)	0.0307 (17)	0.046 (2)	−0.0126 (14)	−0.0089 (15)	0.0008 (14)
C2A	0.0404 (19)	0.0326 (17)	0.046 (2)	−0.0133 (15)	−0.0051 (15)	−0.0065 (15)
C3A	0.067 (3)	0.049 (2)	0.045 (2)	−0.027 (2)	−0.0099 (19)	−0.0033 (17)
C4A	0.066 (3)	0.051 (2)	0.047 (2)	−0.024 (2)	−0.0111 (19)	−0.0098 (18)
C5A	0.041 (2)	0.0349 (19)	0.069 (3)	−0.0153 (16)	−0.0127 (18)	−0.0110 (17)
C6A	0.043 (2)	0.0353 (18)	0.049 (2)	−0.0167 (16)	−0.0068 (16)	0.0026 (15)
C7A	0.046 (2)	0.0349 (18)	0.0398 (19)	−0.0180 (15)	−0.0057 (15)	0.0059 (14)
C8A	0.066 (3)	0.051 (2)	0.038 (2)	−0.034 (2)	−0.0091 (17)	0.0026 (16)
C1B	0.0427 (19)	0.0288 (16)	0.0414 (19)	−0.0138 (14)	−0.0083 (15)	−0.0007 (14)
C2B	0.0396 (19)	0.0324 (17)	0.0413 (19)	−0.0125 (15)	−0.0113 (15)	0.0012 (14)
C3B	0.059 (2)	0.043 (2)	0.0373 (19)	−0.0234 (18)	−0.0098 (17)	0.0011 (15)
C4B	0.052 (2)	0.0390 (19)	0.045 (2)	−0.0216 (17)	−0.0066 (17)	0.0040 (16)
C5B	0.0414 (19)	0.0299 (17)	0.052 (2)	−0.0137 (15)	−0.0099 (16)	−0.0021 (15)
C6B	0.054 (2)	0.0360 (18)	0.0393 (19)	−0.0183 (16)	−0.0086 (16)	−0.0031 (15)
C7B	0.051 (2)	0.0400 (19)	0.0390 (19)	−0.0202 (17)	−0.0066 (16)	−0.0061 (15)
C8B	0.061 (2)	0.058 (2)	0.0362 (19)	−0.034 (2)	−0.0022 (17)	−0.0044 (17)
C1M	0.087 (4)	0.075 (4)	0.151 (6)	−0.011 (3)	−0.063 (4)	−0.008 (4)

Geometric parameters (Å, º)

Mn—O1A	1.893 (2)	C1A—C7A	1.430 (5)
Mn—O1B	1.914 (2)	C2A—C3A	1.397 (5)
Mn—N1B	1.982 (3)	C3A—C4A	1.375 (5)
Mn—N1A	1.994 (3)	C3A—H3AA	0.9300
Mn—O1M	2.233 (3)	C4A—C5A	1.395 (6)
Mn—O1W	2.263 (3)	C4A—H4AA	0.9300
Cl—O13A	1.395 (3)	C5A—C6A	1.369 (5)
Cl—O12A	1.409 (4)	C6A—H6AA	0.9300
Cl—O14A	1.409 (3)	C7A—H7AA	0.9300
Cl—O11A	1.410 (4)	C8A—C8B	1.505 (5)
O1A—C2A	1.320 (4)	C8A—H8AA	0.9700
O1B—C2B	1.313 (4)	C8A—H8AB	0.9700
O1M—C1M	1.385 (6)	C1B—C6B	1.405 (4)
O1M—H1M	0.8200	C1B—C2B	1.411 (5)
O1W—H1W1	0.818 (5)	C1B—C7B	1.433 (5)
O1W—H1W2	0.820 (5)	C2B—C3B	1.421 (5)
O51A—N5A	1.216 (4)	C3B—C4B	1.368 (5)
O52A—N5A	1.239 (4)	C3B—H3BA	0.9300
O51B—N5B	1.215 (4)	C4B—C5B	1.394 (5)
O52B—N5B	1.240 (4)	C4B—H4BA	0.9300
N1A—C7A	1.281 (4)	C5B—C6B	1.357 (5)
N1A—C8A	1.482 (4)	C6B—H6BA	0.9300
N1B—C7B	1.279 (4)	C7B—H7BA	0.9300
N1B—C8B	1.485 (4)	C8B—H8BA	0.9700
N5A—C5A	1.459 (4)	C8B—H8BB	0.9700
N5B—C5B	1.458 (4)	C1M—H1MA	0.9600
C1A—C6A	1.411 (5)	C1M—H1MB	0.9600
C1A—C2A	1.418 (5)	C1M—H1MC	0.9600
O1A—Mn—O1B	96.90 (10)	C3A—C4A—H4AA	120.4
O1A—Mn—N1B	171.73 (11)	C5A—C4A—H4AA	120.4
O1B—Mn—N1B	90.91 (11)	C6A—C5A—C4A	121.3 (3)
O1A—Mn—N1A	90.69 (11)	C6A—C5A—N5A	119.3 (4)
O1B—Mn—N1A	172.11 (11)	C4A—C5A—N5A	119.4 (3)
N1B—Mn—N1A	81.61 (11)	C5A—C6A—C1A	120.0 (3)
O1A—Mn—O1M	89.58 (11)	C5A—C6A—H6AA	120.0
O1B—Mn—O1M	90.50 (11)	C1A—C6A—H6AA	120.0
N1B—Mn—O1M	87.64 (12)	N1A—C7A—C1A	124.6 (3)
N1A—Mn—O1M	91.72 (12)	N1A—C7A—H7AA	117.7
O1A—Mn—O1W	91.05 (11)	C1A—C7A—H7AA	117.7
O1B—Mn—O1W	87.43 (11)	N1A—C8A—C8B	106.9 (3)
N1B—Mn—O1W	92.00 (12)	N1A—C8A—H8AA	110.3
N1A—Mn—O1W	90.28 (12)	C8B—C8A—H8AA	110.3
O1M—Mn—O1W	177.89 (11)	N1A—C8A—H8AB	110.3
O13A—Cl—O12A	109.6 (3)	C8B—C8A—H8AB	110.3
O13A—Cl—O14A	110.1 (2)	H8AA—C8A—H8AB	108.6
O12A—Cl—O14A	110.9 (3)	C6B—C1B—C2B	119.7 (3)
O13A—Cl—O11A	109.3 (3)	C6B—C1B—C7B	116.9 (3)
O12A—Cl—O11A	107.7 (3)	C2B—C1B—C7B	123.4 (3)
O14A—Cl—O11A	109.1 (3)	O1B—C2B—C1B	123.3 (3)
C2A—O1A—Mn	129.3 (2)	O1B—C2B—C3B	118.6 (3)
C2B—O1B—Mn	128.4 (2)	C1B—C2B—C3B	118.1 (3)
C1M—O1M—Mn	130.6 (3)	C4B—C3B—C2B	121.1 (3)
C1M—O1M—H1M	109.5	C4B—C3B—H3BA	119.4
Mn—O1M—H1M	106.9	C2B—C3B—H3BA	119.4
Mn—O1W—H1W1	107 (3)	C3B—C4B—C5B	119.3 (3)
Mn—O1W—H1W2	142 (3)	C3B—C4B—H4BA	120.3
H1W1—O1W—H1W2	110.2 (9)	C5B—C4B—H4BA	120.3
C7A—N1A—C8A	120.4 (3)	C6B—C5B—C4B	121.6 (3)
C7A—N1A—Mn	126.6 (2)	C6B—C5B—N5B	117.8 (3)
C8A—N1A—Mn	113.0 (2)	C4B—C5B—N5B	120.5 (3)
C7B—N1B—C8B	120.0 (3)	C5B—C6B—C1B	120.2 (3)
C7B—N1B—Mn	126.3 (2)	C5B—C6B—H6BA	119.9
C8B—N1B—Mn	113.7 (2)	C1B—C6B—H6BA	119.9
O51A—N5A—O52A	123.4 (3)	N1B—C7B—C1B	125.2 (3)
O51A—N5A—C5A	119.0 (4)	N1B—C7B—H7BA	117.4
O52A—N5A—C5A	117.6 (3)	C1B—C7B—H7BA	117.4
O51B—N5B—O52B	122.3 (3)	N1B—C8B—C8A	106.3 (3)
O51B—N5B—C5B	119.9 (3)	N1B—C8B—H8BA	110.5
O52B—N5B—C5B	117.8 (3)	C8A—C8B—H8BA	110.5
C6A—C1A—C2A	119.2 (3)	N1B—C8B—H8BB	110.5
C6A—C1A—C7A	117.0 (3)	C8A—C8B—H8BB	110.5
C2A—C1A—C7A	123.8 (3)	H8BA—C8B—H8BB	108.7
O1A—C2A—C3A	118.7 (3)	O1M—C1M—H1MA	109.5
O1A—C2A—C1A	122.7 (3)	O1M—C1M—H1MB	109.5
C3A—C2A—C1A	118.6 (3)	H1MA—C1M—H1MB	109.5
C4A—C3A—C2A	121.7 (4)	O1M—C1M—H1MC	109.5
C4A—C3A—H3AA	119.1	H1MA—C1M—H1MC	109.5
C2A—C3A—H3AA	119.1	H1MB—C1M—H1MC	109.5
C3A—C4A—C5A	119.1 (4)
O1B—Mn—O1A—C2A	165.2 (3)	C3A—C4A—C5A—N5A	177.6 (4)
N1A—Mn—O1A—C2A	−17.0 (3)	O51A—N5A—C5A—C6A	−178.2 (4)
O1M—Mn—O1A—C2A	74.7 (3)	O52A—N5A—C5A—C6A	1.8 (5)
O1W—Mn—O1A—C2A	−107.3 (3)	O51A—N5A—C5A—C4A	3.3 (6)
O1A—Mn—O1B—C2B	165.4 (3)	O52A—N5A—C5A—C4A	−176.7 (4)
N1B—Mn—O1B—C2B	−17.3 (3)	C4A—C5A—C6A—C1A	1.7 (6)
O1M—Mn—O1B—C2B	−105.0 (3)	N5A—C5A—C6A—C1A	−176.7 (3)
O1W—Mn—O1B—C2B	74.6 (3)	C2A—C1A—C6A—C5A	−1.0 (5)
O1A—Mn—O1M—C1M	−1.4 (5)	C7A—C1A—C6A—C5A	177.4 (3)
O1B—Mn—O1M—C1M	−98.3 (5)	C8A—N1A—C7A—C1A	176.5 (3)
N1B—Mn—O1M—C1M	170.8 (5)	Mn—N1A—C7A—C1A	−5.6 (5)
N1A—Mn—O1M—C1M	89.2 (5)	C6A—C1A—C7A—N1A	178.2 (3)
O1W—Mn—O1M—C1M	−109 (3)	C2A—C1A—C7A—N1A	−3.5 (6)
O1A—Mn—N1A—C7A	12.8 (3)	C7A—N1A—C8A—C8B	141.1 (3)
O1B—Mn—N1A—C7A	177.0 (7)	Mn—N1A—C8A—C8B	−37.1 (4)
N1B—Mn—N1A—C7A	−164.1 (3)	Mn—O1B—C2B—C1B	13.6 (5)
O1M—Mn—N1A—C7A	−76.8 (3)	Mn—O1B—C2B—C3B	−168.3 (2)
O1W—Mn—N1A—C7A	103.9 (3)	C6B—C1B—C2B—O1B	178.6 (3)
O1A—Mn—N1A—C8A	−169.1 (2)	C7B—C1B—C2B—O1B	1.0 (5)
N1B—Mn—N1A—C8A	13.9 (2)	C6B—C1B—C2B—C3B	0.5 (5)
O1M—Mn—N1A—C8A	101.3 (2)	C7B—C1B—C2B—C3B	−177.1 (3)
O1W—Mn—N1A—C8A	−78.1 (2)	O1B—C2B—C3B—C4B	−178.1 (3)
O1A—Mn—N1B—C7B	173.5 (7)	C1B—C2B—C3B—C4B	0.1 (5)
O1B—Mn—N1B—C7B	12.6 (3)	C2B—C3B—C4B—C5B	−0.7 (6)
N1A—Mn—N1B—C7B	−164.9 (3)	C3B—C4B—C5B—C6B	0.7 (6)
O1M—Mn—N1B—C7B	103.0 (3)	C3B—C4B—C5B—N5B	177.8 (3)
O1W—Mn—N1B—C7B	−74.9 (3)	O51B—N5B—C5B—C6B	−4.2 (5)
O1B—Mn—N1B—C8B	−169.3 (3)	O52B—N5B—C5B—C6B	175.0 (3)
N1A—Mn—N1B—C8B	13.2 (3)	O51B—N5B—C5B—C4B	178.6 (4)
O1M—Mn—N1B—C8B	−78.9 (3)	O52B—N5B—C5B—C4B	−2.2 (5)
O1W—Mn—N1B—C8B	103.2 (3)	C4B—C5B—C6B—C1B	−0.1 (6)
Mn—O1A—C2A—C3A	−167.7 (3)	N5B—C5B—C6B—C1B	−177.2 (3)
Mn—O1A—C2A—C1A	13.8 (5)	C2B—C1B—C6B—C5B	−0.5 (5)
C6A—C1A—C2A—O1A	178.0 (3)	C7B—C1B—C6B—C5B	177.3 (3)
C7A—C1A—C2A—O1A	−0.2 (6)	C8B—N1B—C7B—C1B	177.8 (3)
C6A—C1A—C2A—C3A	−0.5 (5)	Mn—N1B—C7B—C1B	−4.2 (5)
C7A—C1A—C2A—C3A	−178.8 (3)	C6B—C1B—C7B—N1B	176.7 (4)
O1A—C2A—C3A—C4A	−177.2 (4)	C2B—C1B—C7B—N1B	−5.6 (6)
C1A—C2A—C3A—C4A	1.4 (6)	C7B—N1B—C8B—C8A	141.9 (3)
C2A—C3A—C4A—C5A	−0.8 (6)	Mn—N1B—C8B—C8A	−36.4 (4)
C3A—C4A—C5A—C6A	−0.8 (6)	N1A—C8A—C8B—N1B	45.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1M···O52A^i	0.82	2.06	2.877 (4)	179
O1W—H1W1···O52B^ii	0.82 (1)	2.11 (1)	2.905 (4)	166 (5)
O1W—H1W2···O12A	0.82 (1)	2.12 (3)	2.842 (5)	148 (5)

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.