Aqua-{6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}(4-hydroxy-benzoato)manganese(III).

The title compound, [Mn(C(18)H(18)N(2)O(4))(C(7)H(5)O(3))(H(2)O)], was synthesized by a template reaction of ethane-1,2-diamine and 3-methoxy-salicylaldehyde in presence of manganese(II) 4-hydroxy-benzoate. The Jahn-Teller-distorted manganese(III) centre has an octa-hedral geometry. Extensive O-H⋯O hydrogen-bonding inter-actions generate a two-dimensional sheet structure parallel to (103).

Related literature

For background to the coordination chemistry of manganese, see: Christou (2005 ▶); Yocum & Pecoraro (1999 ▶); McEvoy & Brudvig (2006 ▶); Pecoraro (1992 ▶). For the structures of manganese complexes containing Schiff base and carboxyl­ate ligands, see: Bermejo et al. (2006 ▶); Hulme et al. (1997 ▶); Zhang & Janiak (2001 ▶).

Experimental

Crystal data

[Mn(C18H18N2O4)(C7H5O3)(H2O)]

M = 536.41

Monoclinic,

a = 8.5988 (3) Å

b = 13.5524 (5) Å

c = 21.1335 (8) Å

β = 93.280 (2)°

V = 2458.75 (16) Å3

Z = 4

Cu Kα radiation

μ = 4.82 mm−1

T = 100 K

0.43 × 0.38 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2004 ▶) T min = 0.229, T max = 0.388

26252 measured reflections

4259 independent reflections

3766 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.04

4259 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032553/bt5032sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032553/bt5032Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C18H18N2O4)(C7H5O3)(H2O)]	F(000) = 1112
Mr = 536.41	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 305 reflections
a = 8.5988 (3) Å	θ = 9.7–72.7°
b = 13.5524 (5) Å	µ = 4.82 mm−1
c = 21.1335 (8) Å	T = 100 K
β = 93.280 (2)°	Block, red
V = 2458.75 (16) Å3	0.43 × 0.38 × 0.24 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	3766 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω and ψ scans	θmax = 67.0°, θmin = 3.9°
Absorption correction: numerical (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.229, Tmax = 0.388	k = −16→16
26252 measured reflections	l = −25→23

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.482P] where P = (Fo2 + 2Fc2)/3
4259 reflections	(Δ/σ)max = 0.001
329 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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	0.00260 (3)	0.572439 (18)	0.395095 (12)	0.03435 (10)
O1	0.16793 (14)	0.49020 (9)	0.42468 (6)	0.0441 (3)
O2	0.00908 (13)	0.65071 (8)	0.46877 (5)	0.0385 (3)
O3	−0.17820 (15)	0.46814 (10)	0.43826 (6)	0.0462 (3)
H1W	−0.2082	0.4929	0.4719	0.069*
H2W	−0.1324	0.4183	0.4539	0.069*
O4	0.13396 (16)	0.68020 (10)	0.34910 (7)	0.0579 (4)
O5	0.2768 (2)	0.61403 (11)	0.27687 (9)	0.0759 (5)
O6	0.38532 (16)	0.39868 (11)	0.49052 (8)	0.0605 (4)
O7	0.11387 (16)	0.74947 (10)	0.56553 (6)	0.0552 (4)
O8	0.56714 (18)	1.04617 (10)	0.31546 (7)	0.0569 (4)
H8	0.6043	1.0592	0.2805	0.085*
N1	−0.03465 (18)	0.49221 (11)	0.31755 (7)	0.0437 (4)
N2	−0.18769 (17)	0.64264 (11)	0.36080 (7)	0.0404 (3)
C1	0.2130 (2)	0.40534 (13)	0.40135 (9)	0.0434 (4)
C2	0.3325 (2)	0.35296 (14)	0.43583 (10)	0.0504 (5)
C3	0.3854 (3)	0.26389 (16)	0.41349 (13)	0.0669 (7)
H3A	0.4667	0.2299	0.4367	0.080*
C4	0.3210 (3)	0.22341 (17)	0.35735 (13)	0.0716 (7)
H4	0.3571	0.1617	0.3428	0.086*
C5	0.2069 (3)	0.27213 (16)	0.32360 (12)	0.0648 (6)
H5	0.1640	0.2442	0.2852	0.078*
C6	0.1502 (2)	0.36359 (14)	0.34428 (9)	0.0486 (5)
C7	0.0319 (3)	0.41113 (14)	0.30509 (9)	0.0503 (5)
H7	0.0001	0.3795	0.2664	0.060*
C8	−0.1493 (3)	0.53742 (16)	0.27184 (9)	0.0567 (5)
H8A	−0.1983	0.4862	0.2439	0.068*
H8B	−0.0976	0.5861	0.2451	0.068*
C9	−0.2707 (2)	0.58766 (16)	0.30925 (9)	0.0528 (5)
H9A	−0.3339	0.6332	0.2817	0.063*
H9B	−0.3410	0.5381	0.3268	0.063*
C10	−0.2353 (2)	0.72627 (14)	0.37993 (9)	0.0438 (4)
H10	−0.3219	0.7552	0.3569	0.053*
C11	−0.1684 (2)	0.77993 (13)	0.43343 (9)	0.0418 (4)
C12	−0.2294 (3)	0.87431 (15)	0.44637 (11)	0.0568 (5)
H12	−0.3083	0.9018	0.4184	0.068*
C13	−0.1765 (3)	0.92618 (15)	0.49826 (12)	0.0620 (6)
H13	−0.2186	0.9895	0.5063	0.074*
C14	−0.0609 (3)	0.88696 (15)	0.53968 (10)	0.0554 (5)
H14	−0.0246	0.9235	0.5759	0.067*
C15	0.0010 (2)	0.79578 (13)	0.52835 (9)	0.0431 (4)
C16	−0.05175 (19)	0.73910 (12)	0.47489 (8)	0.0363 (4)
C17	0.5190 (2)	0.35790 (19)	0.52483 (14)	0.0759 (8)
H17A	0.4945	0.2914	0.5395	0.114*
H17B	0.5477	0.3999	0.5614	0.114*
H17C	0.6063	0.3546	0.4970	0.114*
C18	0.1804 (3)	0.8014 (2)	0.61902 (12)	0.0785 (7)
H18A	0.2285	0.8625	0.6049	0.118*
H18B	0.2598	0.7601	0.6411	0.118*
H18C	0.0988	0.8173	0.6479	0.118*
C19	0.2422 (2)	0.68274 (13)	0.31186 (9)	0.0416 (4)
C20	0.33056 (19)	0.77892 (12)	0.31102 (8)	0.0363 (4)
C21	0.3153 (2)	0.84743 (13)	0.35946 (8)	0.0418 (4)
H21	0.2480	0.8334	0.3924	0.050*
C22	0.3962 (2)	0.93532 (14)	0.36026 (9)	0.0443 (4)
H22	0.3863	0.9805	0.3942	0.053*
C23	0.4923 (2)	0.95794 (13)	0.31152 (9)	0.0404 (4)
C24	0.5079 (2)	0.89109 (13)	0.26270 (8)	0.0408 (4)
H24	0.5728	0.9061	0.2291	0.049*
C25	0.4281 (2)	0.80217 (13)	0.26320 (8)	0.0392 (4)
H25	0.4407	0.7561	0.2300	0.047*

	U11	U22	U33	U12	U13	U23
Mn1	0.03304 (16)	0.03382 (16)	0.03536 (16)	−0.00183 (11)	−0.00532 (11)	−0.00038 (11)
O1	0.0386 (7)	0.0387 (7)	0.0539 (7)	0.0051 (5)	−0.0062 (6)	−0.0046 (6)
O2	0.0397 (6)	0.0372 (6)	0.0374 (6)	0.0035 (5)	−0.0080 (5)	−0.0011 (5)
O3	0.0461 (7)	0.0452 (7)	0.0467 (7)	−0.0033 (6)	−0.0027 (6)	0.0103 (6)
O4	0.0593 (9)	0.0451 (7)	0.0719 (9)	−0.0112 (6)	0.0266 (7)	−0.0016 (7)
O5	0.0862 (12)	0.0505 (9)	0.0951 (12)	−0.0120 (8)	0.0399 (10)	−0.0203 (9)
O6	0.0405 (8)	0.0569 (8)	0.0830 (11)	0.0106 (6)	−0.0075 (7)	0.0137 (8)
O7	0.0569 (8)	0.0565 (8)	0.0497 (7)	−0.0026 (7)	−0.0175 (6)	−0.0100 (6)
O8	0.0603 (9)	0.0460 (7)	0.0651 (9)	−0.0143 (7)	0.0111 (7)	−0.0042 (7)
N1	0.0502 (9)	0.0412 (8)	0.0392 (8)	−0.0086 (7)	−0.0021 (7)	−0.0021 (7)
N2	0.0379 (8)	0.0449 (9)	0.0371 (7)	−0.0047 (6)	−0.0085 (6)	0.0066 (6)
C1	0.0378 (9)	0.0355 (9)	0.0581 (11)	0.0001 (7)	0.0132 (8)	0.0047 (8)
C2	0.0412 (10)	0.0435 (10)	0.0679 (13)	0.0014 (8)	0.0146 (9)	0.0104 (9)
C3	0.0585 (13)	0.0509 (12)	0.0944 (18)	0.0176 (10)	0.0311 (13)	0.0254 (13)
C4	0.0944 (18)	0.0417 (12)	0.0826 (17)	0.0110 (12)	0.0400 (15)	0.0024 (12)
C5	0.0864 (17)	0.0414 (11)	0.0694 (14)	−0.0010 (11)	0.0304 (13)	−0.0017 (10)
C6	0.0570 (12)	0.0366 (9)	0.0541 (11)	−0.0043 (8)	0.0186 (9)	−0.0033 (8)
C7	0.0621 (13)	0.0444 (11)	0.0449 (10)	−0.0118 (9)	0.0073 (9)	−0.0065 (8)
C8	0.0667 (14)	0.0609 (12)	0.0401 (10)	−0.0046 (11)	−0.0168 (10)	−0.0015 (9)
C9	0.0493 (12)	0.0608 (12)	0.0458 (10)	−0.0047 (9)	−0.0201 (9)	0.0019 (9)
C10	0.0368 (9)	0.0456 (10)	0.0481 (10)	0.0038 (8)	−0.0059 (8)	0.0119 (8)
C11	0.0382 (9)	0.0382 (9)	0.0487 (10)	0.0010 (7)	−0.0006 (8)	0.0060 (8)
C12	0.0538 (12)	0.0460 (11)	0.0704 (14)	0.0108 (9)	0.0013 (10)	0.0096 (10)
C13	0.0704 (15)	0.0392 (11)	0.0774 (15)	0.0079 (10)	0.0126 (12)	−0.0028 (10)
C14	0.0654 (13)	0.0431 (11)	0.0581 (12)	−0.0072 (10)	0.0063 (10)	−0.0081 (10)
C15	0.0423 (10)	0.0422 (10)	0.0448 (10)	−0.0070 (8)	0.0008 (8)	−0.0009 (8)
C16	0.0333 (8)	0.0353 (9)	0.0404 (9)	−0.0037 (7)	0.0031 (7)	0.0027 (7)
C17	0.0381 (12)	0.0765 (16)	0.112 (2)	0.0059 (10)	−0.0078 (12)	0.0371 (15)
C18	0.0805 (17)	0.0893 (18)	0.0625 (14)	−0.0134 (14)	−0.0233 (13)	−0.0233 (13)
C19	0.0412 (10)	0.0394 (9)	0.0440 (10)	0.0015 (8)	0.0007 (8)	0.0025 (8)
C20	0.0319 (8)	0.0391 (9)	0.0374 (9)	0.0023 (7)	−0.0010 (7)	0.0045 (7)
C21	0.0402 (10)	0.0481 (10)	0.0374 (9)	−0.0012 (8)	0.0049 (7)	0.0027 (8)
C22	0.0486 (11)	0.0456 (10)	0.0387 (9)	−0.0015 (8)	0.0012 (8)	−0.0048 (8)
C23	0.0354 (9)	0.0396 (9)	0.0455 (10)	−0.0014 (7)	−0.0028 (8)	0.0044 (8)
C24	0.0346 (9)	0.0463 (10)	0.0420 (9)	0.0024 (8)	0.0055 (7)	0.0066 (8)
C25	0.0383 (9)	0.0406 (9)	0.0386 (9)	0.0033 (7)	0.0031 (7)	−0.0004 (7)

Mn1—O2	1.8821 (11)	C8—C9	1.507 (3)
Mn1—O1	1.8848 (12)	C8—H8A	0.9900
Mn1—N1	1.9774 (15)	C8—H8B	0.9900
Mn1—N2	1.9930 (14)	C9—H9A	0.9900
Mn1—O4	2.1164 (13)	C9—H9B	0.9900
Mn1—O3	2.3257 (12)	C10—C11	1.437 (3)
O1—C1	1.318 (2)	C10—H10	0.9500
O2—C16	1.316 (2)	C11—C16	1.407 (2)
O3—H1W	0.8400	C11—C12	1.415 (3)
O3—H2W	0.8401	C12—C13	1.359 (3)
O4—C19	1.253 (2)	C12—H12	0.9500
O5—C19	1.236 (2)	C13—C14	1.392 (3)
O6—C2	1.366 (3)	C13—H13	0.9500
O6—C17	1.435 (2)	C14—C15	1.372 (3)
O7—C15	1.366 (2)	C14—H14	0.9500
O7—C18	1.424 (2)	C15—C16	1.419 (2)
O8—C23	1.358 (2)	C17—H17A	0.9800
O8—H8	0.8400	C17—H17B	0.9800
N1—C7	1.274 (2)	C17—H17C	0.9800
N1—C8	1.474 (2)	C18—H18A	0.9800
N2—C10	1.278 (2)	C18—H18B	0.9800
N2—C9	1.470 (2)	C18—H18C	0.9800
C1—C6	1.411 (3)	C19—C20	1.509 (2)
C1—C2	1.416 (3)	C20—C25	1.386 (2)
C2—C3	1.383 (3)	C20—C21	1.394 (2)
C3—C4	1.393 (4)	C21—C22	1.379 (3)
C3—H3A	0.9500	C21—H21	0.9500
C4—C5	1.352 (4)	C22—C23	1.391 (3)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.410 (3)	C23—C24	1.385 (3)
C5—H5	0.9500	C24—C25	1.387 (3)
C6—C7	1.428 (3)	C24—H24	0.9500
C7—H7	0.9500	C25—H25	0.9500
O2—Mn1—O1	94.17 (5)	C8—C9—H9A	110.3
O2—Mn1—N1	172.37 (6)	N2—C9—H9B	110.3
O1—Mn1—N1	91.90 (6)	C8—C9—H9B	110.3
O2—Mn1—N2	90.95 (6)	H9A—C9—H9B	108.5
O1—Mn1—N2	172.26 (6)	N2—C10—C11	125.20 (16)
N1—Mn1—N2	82.56 (6)	N2—C10—H10	117.4
O2—Mn1—O4	89.99 (5)	C11—C10—H10	117.4
O1—Mn1—O4	98.52 (6)	C16—C11—C12	119.61 (18)
N1—Mn1—O4	93.68 (6)	C16—C11—C10	122.03 (16)
N2—Mn1—O4	87.26 (6)	C12—C11—C10	118.25 (17)
O2—Mn1—O3	90.40 (5)	C13—C12—C11	120.9 (2)
O1—Mn1—O3	91.09 (5)	C13—C12—H12	119.6
N1—Mn1—O3	84.87 (6)	C11—C12—H12	119.6
N2—Mn1—O3	83.08 (5)	C12—C13—C14	120.26 (19)
O4—Mn1—O3	170.33 (5)	C12—C13—H13	119.9
C1—O1—Mn1	128.61 (12)	C14—C13—H13	119.9
C16—O2—Mn1	126.94 (10)	C15—C14—C13	120.29 (19)
Mn1—O3—H1W	109.5	C15—C14—H14	119.9
Mn1—O3—H2W	109.5	C13—C14—H14	119.9
H1W—O3—H2W	98.5	O7—C15—C14	125.68 (17)
C19—O4—Mn1	137.94 (13)	O7—C15—C16	113.16 (15)
C2—O6—C17	118.09 (18)	C14—C15—C16	121.16 (18)
C15—O7—C18	118.02 (17)	O2—C16—C11	124.73 (15)
C23—O8—H8	109.5	O2—C16—C15	117.41 (15)
C7—N1—C8	120.99 (16)	C11—C16—C15	117.83 (16)
C7—N1—Mn1	126.33 (14)	O6—C17—H17A	109.5
C8—N1—Mn1	112.66 (12)	O6—C17—H17B	109.5
C10—N2—C9	122.20 (16)	H17A—C17—H17B	109.5
C10—N2—Mn1	125.41 (12)	O6—C17—H17C	109.5
C9—N2—Mn1	112.39 (12)	H17A—C17—H17C	109.5
O1—C1—C6	124.27 (17)	H17B—C17—H17C	109.5
O1—C1—C2	117.72 (18)	O7—C18—H18A	109.5
C6—C1—C2	118.01 (18)	O7—C18—H18B	109.5
O6—C2—C3	125.8 (2)	H18A—C18—H18B	109.5
O6—C2—C1	113.84 (17)	O7—C18—H18C	109.5
C3—C2—C1	120.4 (2)	H18A—C18—H18C	109.5
C2—C3—C4	120.8 (2)	H18B—C18—H18C	109.5
C2—C3—H3A	119.6	O5—C19—O4	124.60 (18)
C4—C3—H3A	119.6	O5—C19—C20	120.33 (16)
C5—C4—C3	119.9 (2)	O4—C19—C20	115.06 (16)
C5—C4—H4	120.0	C25—C20—C21	118.07 (16)
C3—C4—H4	120.0	C25—C20—C19	122.08 (16)
C4—C5—C6	121.3 (2)	C21—C20—C19	119.86 (15)
C4—C5—H5	119.4	C22—C21—C20	121.03 (16)
C6—C5—H5	119.4	C22—C21—H21	119.5
C5—C6—C1	119.7 (2)	C20—C21—H21	119.5
C5—C6—C7	117.6 (2)	C21—C22—C23	120.13 (17)
C1—C6—C7	122.67 (17)	C21—C22—H22	119.9
N1—C7—C6	125.66 (18)	C23—C22—H22	119.9
N1—C7—H7	117.2	O8—C23—C24	123.75 (16)
C6—C7—H7	117.2	O8—C23—C22	116.63 (17)
N1—C8—C9	107.53 (16)	C24—C23—C22	119.62 (16)
N1—C8—H8A	110.2	C23—C24—C25	119.58 (16)
C9—C8—H8A	110.2	C23—C24—H24	120.2
N1—C8—H8B	110.2	C25—C24—H24	120.2
C9—C8—H8B	110.2	C20—C25—C24	121.55 (16)
H8A—C8—H8B	108.5	C20—C25—H25	119.2
N2—C9—C8	107.24 (16)	C24—C25—H25	119.2
N2—C9—H9A	110.3
O2—Mn1—O1—C1	167.31 (14)	Mn1—N1—C7—C6	−1.8 (3)
N1—Mn1—O1—C1	−8.07 (15)	C5—C6—C7—N1	177.95 (19)
O4—Mn1—O1—C1	−102.08 (15)	C1—C6—C7—N1	−3.2 (3)
O3—Mn1—O1—C1	76.83 (14)	C7—N1—C8—C9	145.79 (18)
O1—Mn1—O2—C16	162.00 (13)	Mn1—N1—C8—C9	−35.67 (19)
N2—Mn1—O2—C16	−23.80 (14)	C10—N2—C9—C8	143.81 (18)
O4—Mn1—O2—C16	63.46 (14)	Mn1—N2—C9—C8	−35.78 (19)
O3—Mn1—O2—C16	−106.88 (13)	N1—C8—C9—N2	45.1 (2)
O2—Mn1—O4—C19	140.4 (2)	C9—N2—C10—C11	174.25 (17)
O1—Mn1—O4—C19	46.2 (2)	Mn1—N2—C10—C11	−6.2 (3)
N1—Mn1—O4—C19	−46.3 (2)	N2—C10—C11—C16	−7.3 (3)
N2—Mn1—O4—C19	−128.6 (2)	N2—C10—C11—C12	176.57 (18)
O1—Mn1—N1—C7	6.06 (17)	C16—C11—C12—C13	0.2 (3)
N2—Mn1—N1—C7	−168.52 (17)	C10—C11—C12—C13	176.4 (2)
O4—Mn1—N1—C7	104.73 (16)	C11—C12—C13—C14	0.0 (3)
O3—Mn1—N1—C7	−84.86 (16)	C12—C13—C14—C15	0.2 (3)
O1—Mn1—N1—C8	−172.39 (13)	C18—O7—C15—C14	−3.6 (3)
N2—Mn1—N1—C8	13.03 (13)	C18—O7—C15—C16	177.24 (18)
O4—Mn1—N1—C8	−73.72 (13)	C13—C14—C15—O7	−179.66 (19)
O3—Mn1—N1—C8	96.69 (13)	C13—C14—C15—C16	−0.6 (3)
O2—Mn1—N2—C10	17.80 (15)	Mn1—O2—C16—C11	18.7 (2)
N1—Mn1—N2—C10	−166.21 (16)	Mn1—O2—C16—C15	−163.44 (12)
O4—Mn1—N2—C10	−72.14 (15)	C12—C11—C16—O2	177.39 (17)
O3—Mn1—N2—C10	108.09 (15)	C10—C11—C16—O2	1.3 (3)
O2—Mn1—N2—C9	−162.63 (13)	C12—C11—C16—C15	−0.5 (3)
N1—Mn1—N2—C9	13.36 (13)	C10—C11—C16—C15	−176.59 (16)
O4—Mn1—N2—C9	107.43 (13)	O7—C15—C16—O2	1.9 (2)
O3—Mn1—N2—C9	−72.34 (13)	C14—C15—C16—O2	−177.34 (17)
Mn1—O1—C1—C6	5.9 (3)	O7—C15—C16—C11	179.91 (15)
Mn1—O1—C1—C2	−174.29 (12)	C14—C15—C16—C11	0.7 (3)
C17—O6—C2—C3	7.6 (3)	Mn1—O4—C19—O5	21.3 (3)
C17—O6—C2—C1	−172.48 (17)	Mn1—O4—C19—C20	−159.68 (14)
O1—C1—C2—O6	0.6 (2)	O5—C19—C20—C25	14.1 (3)
C6—C1—C2—O6	−179.62 (16)	O4—C19—C20—C25	−164.99 (17)
O1—C1—C2—C3	−179.53 (17)	O5—C19—C20—C21	−165.88 (18)
C6—C1—C2—C3	0.3 (3)	O4—C19—C20—C21	15.1 (2)
O6—C2—C3—C4	178.98 (19)	C25—C20—C21—C22	−0.8 (3)
C1—C2—C3—C4	−0.9 (3)	C19—C20—C21—C22	179.17 (17)
C2—C3—C4—C5	1.0 (3)	C20—C21—C22—C23	1.5 (3)
C3—C4—C5—C6	−0.4 (3)	C21—C22—C23—O8	179.52 (17)
C4—C5—C6—C1	−0.2 (3)	C21—C22—C23—C24	−0.9 (3)
C4—C5—C6—C7	178.7 (2)	O8—C23—C24—C25	179.18 (16)
O1—C1—C6—C5	−179.94 (17)	C22—C23—C24—C25	−0.4 (3)
C2—C1—C6—C5	0.2 (3)	C21—C20—C25—C24	−0.5 (3)
O1—C1—C6—C7	1.3 (3)	C19—C20—C25—C24	179.53 (15)
C2—C1—C6—C7	−178.54 (17)	C23—C24—C25—C20	1.1 (3)
C8—N1—C7—C6	176.51 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O5i	0.84	1.79	2.599 (2)	161
O3—H2W···O7ii	0.84	2.32	3.0025 (19)	139
O3—H2W···O2ii	0.84	2.11	2.8711 (17)	150
O3—H1W···O6ii	0.84	2.29	3.000 (2)	142
O3—H1W···O1ii	0.84	2.21	2.9475 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O5i	0.84	1.79	2.599 (2)	161
O3—H2W⋯O7ii	0.84	2.32	3.0025 (19)	139
O3—H2W⋯O2ii	0.84	2.11	2.8711 (17)	150
O3—H1W⋯O6ii	0.84	2.29	3.000 (2)	142
O3—H1W⋯O1ii	0.84	2.21	2.9475 (18)	147

Symmetry codes: (i) ; (ii) .