Hexa-μ(2)-benzoato-bis-(2,2'-bipyrid-yl)trimanganese(II) monohydrate.

The complex molecule of the title compound, [Mn(3)(C(7)H(5)O(2))(6)(C(10)H(8)N(2))(2)]·H(2)O, contains a linear array of divalent manganese ions. The central Mn(II) atom, which is located on a crystallographic inversion center, is coordinated octa-hedrally by six benzoate O atoms. The two terminal Mn(II) ions are six-coordinated by four benzoate O atoms and two N atoms of 2,2'-bipyridyl. The central Mn(II) atom and the terminal Mn(II) ions are bridged by four benzoate ligands in a bidentate fashion, whereas the other two carboxyl-ate ligands form bridges through one O atom only and chelate the terminal Mn(II) atom. The mol-ecules pack together via van der Waals attractions and C-H⋯O hydrogen bonds.

Related literature

For general background, see: Mukhopadhyay et al. (2002 ▶) and references therein; Gatteschi et al. (2003 ▶) and references therein; Yao et al. (2006 ▶); Ma et al. (2007 ▶). For related literature, see: Desiraju et al. (2002 ▶) and references therein. For related structures, see: Ménage et al. (1991 ▶); Tangoulis et al. (1996 ▶); Fernández et al. (2002 ▶).

Experimental

Crystal data

[Mn3(C7H5O2)6(C10H8N2)2]·H2O

M = 1221.86

Triclinic,

a = 11.2312 (5) Å

b = 11.7544 (2) Å

c = 11.994 (3) Å

α = 72.046 (3)°

β = 71.094 (1)°

γ = 80.418 (2)°

V = 1421.1 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 291 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.841, T max = 0.932

11367 measured reflections

5553 independent reflections

4007 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.138

S = 1.08

5553 reflections

382 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012518/rk2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012518/rk2087Isup2.hkl

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

[Mn3(C7H5O2)6(C10H8N2)2]·H2O	Z = 1
Mr = 1221.86	F000 = 627
Triclinic, P1	Dx = 1.428 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.2312 (5) Å	Cell parameters from 4735 reflections
b = 11.7544 (2) Å	θ = 2.1–26.5º
c = 11.994 (3) Å	µ = 0.73 mm−1
α = 72.046 (3)º	T = 291 (2) K
β = 71.0940 (10)º	Block, dark–brown
γ = 80.418 (2)º	0.30 × 0.20 × 0.10 mm
V = 1421.1 (4) Å3

Bruker SMART APEX CCD diffractometer	5553 independent reflections
Radiation source: Sealed tube	4007 reflections with I > 2σ(I)
Monochromator: Ggraphite	Rint = 0.036
T = 291(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.841, Tmax = 0.932	k = −14→14
11367 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: Full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
5553 reflections	Δρmax = 0.29 e Å−3
382 parameters	Δρmin = −0.70 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
C1	0.7698 (3)	0.7996 (3)	0.3087 (3)	0.0385 (8)
C2	0.8860 (4)	0.7842 (4)	0.2269 (4)	0.0525 (10)
H2	0.9590	0.7944	0.2423	0.063*
C3	0.8943 (4)	0.7532 (4)	0.1208 (4)	0.0589 (11)
H3	0.9724	0.7449	0.0644	0.071*
C4	0.7860 (4)	0.7353 (4)	0.1005 (4)	0.0572 (10)
H4	0.7914	0.7139	0.0304	0.069*
C5	0.6702 (4)	0.7485 (4)	0.1825 (4)	0.0546 (10)
H5	0.5980	0.7351	0.1678	0.066*
C6	0.6594 (4)	0.7815 (3)	0.2865 (4)	0.0496 (9)
H6	0.5805	0.7916	0.3411	0.060*
C7	0.7607 (3)	0.8311 (3)	0.4229 (3)	0.0369 (7)
C8	0.7418 (3)	1.2525 (3)	0.5247 (3)	0.0364 (7)
C9	0.8542 (3)	1.2741 (3)	0.5377 (4)	0.0454 (9)
H9	0.9084	1.2099	0.5641	0.054*
C10	0.8856 (4)	1.3894 (4)	0.5120 (4)	0.0489 (9)
H10	0.9613	1.4029	0.5199	0.059*
C11	0.8053 (4)	1.4850 (3)	0.4745 (4)	0.0503 (9)
H11	0.8251	1.5630	0.4598	0.060*
C12	0.6939 (4)	1.4641 (3)	0.4587 (4)	0.0519 (10)
H12	0.6410	1.5284	0.4301	0.062*
C13	0.6621 (3)	1.3488 (3)	0.4851 (3)	0.0401 (8)
H13	0.5867	1.3355	0.4763	0.048*
C14	0.7122 (3)	1.1261 (3)	0.5471 (3)	0.0312 (6)
C15	0.3814 (3)	0.9013 (3)	0.9078 (3)	0.0361 (7)
C16	0.4312 (4)	0.8754 (3)	1.0053 (3)	0.0448 (8)
H16	0.5171	0.8538	0.9926	0.054*
C17	0.3569 (4)	0.8806 (3)	1.1204 (3)	0.0471 (9)
H17	0.3920	0.8627	1.1847	0.056*
C18	0.2299 (4)	0.9127 (4)	1.1389 (3)	0.0513 (10)
H18	0.1788	0.9167	1.2163	0.062*
C19	0.1785 (4)	0.9388 (4)	1.0444 (3)	0.0513 (10)
H19	0.0926	0.9603	1.0576	0.062*
C20	0.2541 (3)	0.9332 (3)	0.9284 (3)	0.0450 (8)
H20	0.2185	0.9511	0.8644	0.054*
C21	0.4675 (3)	0.9023 (3)	0.7814 (3)	0.0355 (7)
C22	0.9965 (3)	0.8848 (4)	0.6997 (3)	0.0449 (8)
H22	0.9783	0.9660	0.6664	0.054*
C23	1.1066 (4)	0.8490 (4)	0.7370 (4)	0.0521 (9)
H23	1.1606	0.9051	0.7286	0.063*
C24	1.1315 (4)	0.7329 (4)	0.7846 (4)	0.0543 (10)
H24	1.2029	0.7072	0.8114	0.065*
C25	1.0518 (4)	0.6497 (4)	0.7947 (4)	0.0577 (11)
H25	1.0705	0.5682	0.8264	0.069*
C26	0.9434 (4)	0.6893 (4)	0.7568 (4)	0.0491 (9)
C27	0.8531 (4)	0.6079 (3)	0.7629 (4)	0.0534 (10)
C28	0.8616 (5)	0.4857 (4)	0.8167 (4)	0.0660 (12)
H28	0.9259	0.4506	0.8522	0.079*
C29	0.7743 (4)	0.4173 (4)	0.8172 (4)	0.0615 (12)
H29	0.7790	0.3352	0.8540	0.074*
C30	0.6809 (4)	0.4675 (4)	0.7648 (4)	0.0605 (11)
H30	0.6216	0.4210	0.7649	0.073*
C31	0.6762 (4)	0.5914 (4)	0.7106 (4)	0.0562 (10)
H31	0.6119	0.6273	0.6754	0.067*
Mn1	0.5000	1.0000	0.5000	0.03159 (18)
Mn2	0.74951 (5)	0.86247 (4)	0.63436 (5)	0.03183 (15)
N1	0.9164 (3)	0.8058 (3)	0.7104 (3)	0.0423 (7)
N2	0.7615 (3)	0.6596 (3)	0.7081 (3)	0.0508 (8)
O1	0.6536 (2)	0.8502 (2)	0.4961 (2)	0.0391 (5)
O2	0.8604 (2)	0.8344 (2)	0.4472 (2)	0.0439 (6)
O3	0.6136 (2)	1.1124 (2)	0.5272 (2)	0.0458 (6)
O4	0.7876 (2)	1.0433 (2)	0.5852 (2)	0.0423 (6)
O5	0.5826 (2)	0.8747 (2)	0.7718 (2)	0.0441 (6)
O6	0.4186 (2)	0.9293 (2)	0.6956 (2)	0.0419 (6)
O1W	0.4239 (7)	0.4880 (6)	0.9786 (6)	0.0601 (16)	0.50
H1A	0.477 (11)	0.463 (9)	1.019 (11)	0.072*	0.50
H1B	0.369 (10)	0.538 (9)	1.009 (9)	0.072*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0372 (17)	0.0400 (18)	0.0360 (18)	0.0098 (15)	−0.0094 (14)	−0.0151 (15)
C2	0.049 (2)	0.050 (2)	0.046 (2)	0.0097 (18)	−0.0083 (17)	−0.0080 (18)
C3	0.058 (3)	0.064 (3)	0.048 (2)	0.016 (2)	−0.015 (2)	−0.018 (2)
C4	0.057 (2)	0.052 (2)	0.055 (2)	0.0120 (19)	−0.015 (2)	−0.013 (2)
C5	0.058 (2)	0.051 (2)	0.053 (2)	0.0051 (19)	−0.015 (2)	−0.0171 (19)
C6	0.051 (2)	0.050 (2)	0.050 (2)	−0.0006 (18)	−0.0131 (18)	−0.0185 (18)
C7	0.0314 (17)	0.0371 (17)	0.0416 (18)	0.0034 (13)	−0.0111 (14)	−0.0123 (15)
C8	0.0300 (16)	0.0370 (17)	0.0381 (17)	−0.0062 (14)	−0.0056 (13)	−0.0073 (14)
C9	0.0373 (19)	0.043 (2)	0.057 (2)	−0.0079 (16)	−0.0130 (17)	−0.0125 (17)
C10	0.051 (2)	0.052 (2)	0.053 (2)	−0.0175 (18)	−0.0137 (18)	−0.0209 (18)
C11	0.058 (2)	0.037 (2)	0.058 (2)	−0.0135 (18)	−0.0113 (19)	−0.0169 (17)
C12	0.053 (2)	0.037 (2)	0.054 (2)	0.0064 (18)	−0.0139 (19)	−0.0031 (17)
C13	0.045 (2)	0.0393 (18)	0.0344 (18)	−0.0028 (15)	−0.0203 (15)	0.0019 (14)
C14	0.0278 (15)	0.0362 (16)	0.0293 (16)	−0.0020 (13)	−0.0063 (12)	−0.0109 (13)
C15	0.0365 (18)	0.0329 (16)	0.0335 (16)	−0.0069 (14)	−0.0056 (13)	−0.0040 (13)
C16	0.046 (2)	0.051 (2)	0.0355 (18)	0.0003 (17)	−0.0087 (16)	−0.0147 (16)
C17	0.057 (2)	0.051 (2)	0.0338 (18)	−0.0042 (18)	−0.0148 (17)	−0.0104 (16)
C18	0.057 (2)	0.052 (2)	0.0324 (19)	0.0003 (19)	0.0024 (17)	−0.0137 (17)
C19	0.046 (2)	0.055 (2)	0.038 (2)	0.0038 (18)	−0.0014 (16)	−0.0083 (17)
C20	0.0410 (19)	0.054 (2)	0.0337 (19)	−0.0038 (16)	−0.0095 (15)	−0.0038 (16)
C21	0.0381 (18)	0.0377 (17)	0.0316 (17)	−0.0053 (14)	−0.0087 (14)	−0.0109 (13)
C22	0.0337 (18)	0.058 (2)	0.045 (2)	−0.0045 (16)	−0.0126 (16)	−0.0150 (18)
C23	0.044 (2)	0.055 (2)	0.055 (2)	−0.0048 (18)	−0.0130 (18)	−0.0110 (19)
C24	0.049 (2)	0.055 (2)	0.051 (2)	0.0158 (19)	−0.0130 (18)	−0.0155 (19)
C25	0.050 (2)	0.056 (2)	0.052 (2)	0.014 (2)	−0.0111 (19)	−0.0068 (19)
C26	0.046 (2)	0.055 (2)	0.043 (2)	0.0117 (18)	−0.0175 (17)	−0.0133 (18)
C27	0.053 (2)	0.038 (2)	0.057 (2)	0.0160 (18)	−0.0121 (19)	−0.0095 (18)
C28	0.066 (3)	0.048 (2)	0.069 (3)	−0.004 (2)	−0.023 (2)	0.007 (2)
C29	0.061 (3)	0.049 (2)	0.059 (3)	−0.011 (2)	−0.020 (2)	0.013 (2)
C30	0.052 (2)	0.051 (2)	0.067 (3)	−0.017 (2)	−0.018 (2)	0.006 (2)
C31	0.059 (3)	0.054 (2)	0.056 (3)	−0.014 (2)	−0.026 (2)	−0.002 (2)
Mn1	0.0309 (4)	0.0296 (4)	0.0336 (4)	−0.0016 (3)	−0.0084 (3)	−0.0091 (3)
Mn2	0.0282 (3)	0.0330 (3)	0.0353 (3)	0.00136 (19)	−0.0123 (2)	−0.0091 (2)
N1	0.0362 (16)	0.0501 (18)	0.0422 (16)	0.0069 (13)	−0.0157 (13)	−0.0155 (14)
N2	0.0525 (19)	0.0386 (17)	0.057 (2)	−0.0001 (15)	−0.0145 (16)	−0.0105 (15)
O1	0.0311 (12)	0.0478 (14)	0.0392 (13)	0.0059 (10)	−0.0112 (10)	−0.0167 (11)
O2	0.0318 (12)	0.0555 (15)	0.0466 (14)	0.0069 (11)	−0.0138 (11)	−0.0200 (12)
O3	0.0367 (13)	0.0517 (15)	0.0519 (15)	−0.0090 (11)	−0.0094 (11)	−0.0190 (12)
O4	0.0375 (13)	0.0357 (13)	0.0546 (16)	−0.0019 (10)	−0.0179 (12)	−0.0095 (11)
O5	0.0388 (14)	0.0503 (15)	0.0379 (13)	0.0044 (11)	−0.0074 (10)	−0.0124 (11)
O6	0.0432 (13)	0.0556 (15)	0.0260 (12)	−0.0107 (11)	−0.0074 (10)	−0.0091 (11)
O1W	0.060 (4)	0.049 (3)	0.064 (4)	−0.005 (3)	−0.009 (3)	−0.015 (3)

C1—C2	1.378 (5)	C19—H19	0.9300
C1—C6	1.411 (5)	C20—H20	0.9300
C1—C7	1.494 (5)	C21—O6	1.251 (4)
C2—C3	1.400 (6)	C21—O5	1.256 (4)
C2—H2	0.9300	C22—N1	1.348 (5)
C3—C4	1.375 (6)	C22—C23	1.406 (5)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.372 (6)	C23—C24	1.327 (6)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.380 (6)	C24—C25	1.386 (6)
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.395 (6)
C7—O2	1.254 (4)	C25—H25	0.9300
C7—O1	1.271 (4)	C26—N1	1.334 (5)
C7—Mn2	2.634 (4)	C26—C27	1.478 (6)
C8—C13	1.384 (5)	C27—N2	1.358 (5)
C8—C9	1.394 (5)	C27—C28	1.382 (6)
C8—C14	1.499 (5)	C28—C29	1.365 (7)
C9—C10	1.374 (5)	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.355 (6)
C10—C11	1.375 (6)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.400 (6)
C11—C12	1.396 (6)	C30—H30	0.9300
C11—H11	0.9300	C31—N2	1.334 (5)
C12—C13	1.374 (5)	C31—H31	0.9300
C12—H12	0.9300	Mn1—O3i	2.139 (2)
C13—H13	0.9300	Mn1—O3	2.139 (2)
C14—O3	1.251 (4)	Mn1—O6i	2.166 (2)
C14—O4	1.254 (4)	Mn1—O6	2.166 (2)
C15—C20	1.377 (5)	Mn1—O1	2.251 (2)
C15—C16	1.385 (5)	Mn1—O1i	2.251 (2)
C15—C21	1.509 (5)	Mn2—O5	2.075 (2)
C16—C17	1.377 (5)	Mn2—O4	2.101 (2)
C16—H16	0.9300	Mn2—N1	2.259 (3)
C17—C18	1.376 (6)	Mn2—N2	2.271 (3)
C17—H17	0.9300	Mn2—O2	2.282 (3)
C18—C19	1.366 (6)	Mn2—O1	2.300 (2)
C18—H18	0.9300	O1W—H1A	0.85 (13)
C19—C20	1.390 (5)	O1W—H1B	0.85 (10)
C2—C1—C6	119.8 (3)	C25—C24—H24	119.7
C2—C1—C7	120.3 (3)	C24—C25—C26	119.3 (4)
C6—C1—C7	119.9 (3)	C24—C25—H25	120.4
C1—C2—C3	120.1 (4)	C26—C25—H25	120.4
C1—C2—H2	120.0	N1—C26—C25	120.8 (4)
C3—C2—H2	120.0	N1—C26—C27	115.7 (3)
C4—C3—C2	119.5 (4)	C25—C26—C27	123.5 (4)
C4—C3—H3	120.2	N2—C27—C28	120.9 (4)
C2—C3—H3	120.2	N2—C27—C26	115.9 (3)
C5—C4—C3	120.7 (4)	C28—C27—C26	123.2 (4)
C5—C4—H4	119.6	C29—C28—C27	119.2 (4)
C3—C4—H4	119.6	C29—C28—H28	120.4
C4—C5—C6	120.8 (4)	C27—C28—H28	120.4
C4—C5—H5	119.6	C30—C29—C28	120.8 (4)
C6—C5—H5	119.6	C30—C29—H29	119.6
C5—C6—C1	119.0 (4)	C28—C29—H29	119.6
C5—C6—H6	120.5	C29—C30—C31	118.2 (4)
C1—C6—H6	120.5	C29—C30—H30	120.9
O2—C7—O1	120.7 (3)	C31—C30—H30	120.9
O2—C7—C1	118.8 (3)	N2—C31—C30	121.8 (4)
O1—C7—C1	120.5 (3)	N2—C31—H31	119.1
O2—C7—Mn2	60.01 (18)	C30—C31—H31	119.1
O1—C7—Mn2	60.82 (17)	O3i—Mn1—O3	180.0
C1—C7—Mn2	174.0 (2)	O3i—Mn1—O6i	91.63 (10)
C13—C8—C9	119.1 (3)	O3—Mn1—O6i	88.37 (10)
C13—C8—C14	121.0 (3)	O3i—Mn1—O6	88.37 (10)
C9—C8—C14	119.8 (3)	O3—Mn1—O6	91.63 (10)
C10—C9—C8	120.6 (4)	O6i—Mn1—O6	180.000 (1)
C10—C9—H9	119.7	O3i—Mn1—O1	87.97 (9)
C8—C9—H9	119.7	O3—Mn1—O1	92.03 (9)
C9—C10—C11	120.2 (4)	O6i—Mn1—O1	88.49 (9)
C9—C10—H10	119.9	O6—Mn1—O1	91.51 (9)
C11—C10—H10	119.9	O3i—Mn1—O1i	92.03 (9)
C10—C11—C12	119.6 (3)	O3—Mn1—O1i	87.97 (9)
C10—C11—H11	120.2	O6i—Mn1—O1i	91.51 (9)
C12—C11—H11	120.2	O6—Mn1—O1i	88.49 (9)
C13—C12—C11	120.3 (3)	O1—Mn1—O1i	180.000 (1)
C13—C12—H12	119.9	O5—Mn2—O4	96.34 (10)
C11—C12—H12	119.9	O5—Mn2—N1	111.32 (11)
C12—C13—C8	120.3 (3)	O4—Mn2—N1	90.61 (11)
C12—C13—H13	119.9	O5—Mn2—N2	90.34 (11)
C8—C13—H13	119.9	O4—Mn2—N2	162.30 (11)
O3—C14—O4	125.6 (3)	N1—Mn2—N2	71.69 (12)
O3—C14—C8	116.9 (3)	O5—Mn2—O2	152.16 (10)
O4—C14—C8	117.5 (3)	O4—Mn2—O2	94.63 (10)
C20—C15—C16	118.3 (3)	N1—Mn2—O2	94.03 (10)
C20—C15—C21	121.6 (3)	N2—Mn2—O2	86.83 (11)
C16—C15—C21	120.0 (3)	O5—Mn2—O1	95.16 (9)
C17—C16—C15	121.7 (4)	O4—Mn2—O1	105.17 (9)
C17—C16—H16	119.2	N1—Mn2—O1	147.59 (9)
C15—C16—H16	119.2	N2—Mn2—O1	90.47 (11)
C18—C17—C16	119.1 (4)	O2—Mn2—O1	57.22 (8)
C18—C17—H17	120.4	O5—Mn2—C7	123.82 (10)
C16—C17—H17	120.4	O4—Mn2—C7	102.37 (11)
C19—C18—C17	120.3 (4)	N1—Mn2—C7	120.78 (10)
C19—C18—H18	119.8	N2—Mn2—C7	87.25 (12)
C17—C18—H18	119.8	O2—Mn2—C7	28.41 (9)
C18—C19—C20	120.3 (4)	O1—Mn2—C7	28.86 (9)
C18—C19—H19	119.8	C26—N1—C22	118.7 (3)
C20—C19—H19	119.8	C26—N1—Mn2	118.9 (3)
C15—C20—C19	120.3 (4)	C22—N1—Mn2	122.1 (2)
C15—C20—H20	119.9	C31—N2—C27	119.1 (4)
C19—C20—H20	119.9	C31—N2—Mn2	123.1 (3)
O6—C21—O5	125.6 (3)	C27—N2—Mn2	117.4 (3)
O6—C21—C15	117.7 (3)	C7—O1—Mn1	136.2 (2)
O5—C21—C15	116.7 (3)	C7—O1—Mn2	90.3 (2)
N1—C22—C23	122.5 (4)	Mn1—O1—Mn2	104.10 (9)
N1—C22—H22	118.8	C7—O2—Mn2	91.6 (2)
C23—C22—H22	118.8	C14—O3—Mn1	149.7 (2)
C24—C23—C22	118.2 (4)	C14—O4—Mn2	121.3 (2)
C24—C23—H23	120.9	C21—O5—Mn2	138.0 (2)
C22—C23—H23	120.9	C21—O6—Mn1	130.7 (2)
C23—C24—C25	120.5 (4)	H1A—O1W—H1B	109 (10)
C23—C24—H24	119.7

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.93	2.56	3.458 (5)	161
C9—H9···O2ii	0.93	2.53	3.287 (5)	139
C22—H22···O4	0.93	2.55	3.149 (5)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.93	2.56	3.458 (5)	161
C9—H9⋯O2ii	0.93	2.53	3.287 (5)	139
C22—H22⋯O4	0.93	2.55	3.149 (5)	122

Symmetry codes: (i) ; (ii) .