Hexakis(1H-imidazole-κN)mangan-ese(II) triaqua-tris(1H-imidazole-κN)manganese(II) bis-(naphthalene-1,4-dicarboxyl-ate).

In the crystal structure of the title compound, [Mn(C(3)H(4)N(2))(6)][Mn(C(3)H(4)N(2))(3)(H(2)O)(3)](C(12)H(6)O(4))(2), there are uncoordinated naphthalene-dicarboxyl-ate dianions and two kinds of Mn(II) complex cations, both assuming a distorted octa-hedral geometry. One Mn(II) cation is located on an inversion center and is coordinated by six imidazole mol-ecules, while the other Mn(II) cation is located on a twofold rotation axis and is coordinated by three water mol-ecules and three imidazole units. The naphthalene-dicarboxyl-ate dianions are linked to both Mn(II) complex cations via O-H⋯O and N-H⋯O hydrogen bonding, but no π-π stacking is observed between aromatic rings in the crystal structure.

Related literature

For general background, see: Su & Xu (2004 ▶); Liu et al. (2004 ▶). For a related structure, see: Derissen et al. (1979 ▶).

Experimental

Crystal data

[Mn(C3H4N2)6][Mn(C3H4N2)3(H2O)3](C12H6O4)2

M = 1205.0

Orthorhombic,

a = 29.605 (4) Å

b = 9.4619 (12) Å

c = 20.534 (3) Å

V = 5752.0 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 295 (2) K

0.33 × 0.30 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.790, T max = 0.912

61105 measured reflections

5131 independent reflections

4174 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.07

5131 reflections

367 parameters

5 restraints

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −0.66 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011677/sg2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011677/sg2237Isup2.hkl

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

[Mn(C3H4N2)6][Mn(C3H4N2)3(H2O1)3](C12H6O4)2	F000 = 2496
Mr = 1205.0	Dx = 1.391 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 6856 reflections
a = 29.605 (4) Å	θ = 3.0–24.0º
b = 9.4619 (12) Å	µ = 0.51 mm−1
c = 20.534 (3) Å	T = 295 (2) K
V = 5752.0 (14) Å3	Prism, yellow
Z = 4	0.33 × 0.30 × 0.18 mm

Rigaku R-AXIS RAPID IP diffractometer	5131 independent reflections
Radiation source: fine-focus sealed tube	4174 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
Detector resolution: 10.0 pixels mm-1	θmax = 25.2º
T = 295(2) K	θmin = 1.4º
ω scans	h = −35→35
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −11→10
Tmin = 0.790, Tmax = 0.912	l = −24→24
61105 measured reflections

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0611P)2 + 4.7866P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
5131 reflections	Δρmax = 1.06 e Å−3
367 parameters	Δρmin = −0.66 e Å−3
5 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
Mn1	0.5000	0.0000	0.5000	0.04145 (18)
Mn2	0.7500	0.7500	0.54180 (3)	0.04268 (18)
N1	0.53293 (9)	0.2142 (3)	0.50330 (12)	0.0505 (6)
N2	0.58426 (10)	0.3776 (3)	0.48747 (15)	0.0678 (8)
H2N	0.6061	0.4234	0.4696	0.081*
N3	0.54774 (8)	−0.0725 (3)	0.57988 (12)	0.0485 (6)
N4	0.58594 (9)	−0.2212 (3)	0.64106 (13)	0.0560 (7)
H4N	0.5943	−0.2989	0.6591	0.067*
N5	0.44833 (8)	0.0685 (3)	0.57579 (12)	0.0520 (6)
N6	0.41219 (10)	0.0705 (3)	0.66934 (14)	0.0634 (8)
H6N	0.4064	0.0574	0.7099	0.076*
N7	0.71986 (9)	0.9721 (3)	0.54032 (13)	0.0562 (7)
N8	0.69433 (10)	1.1818 (3)	0.56814 (17)	0.0687 (8)
H8N	0.6860	1.2514	0.5923	0.082*
O1	0.65926 (8)	0.0707 (2)	0.13121 (11)	0.0653 (6)
O2	0.60909 (8)	−0.0251 (2)	0.19895 (10)	0.0606 (6)
O3	0.69820 (10)	0.6144 (3)	0.35534 (12)	0.0948 (10)
O4	0.65304 (8)	0.5144 (3)	0.42532 (10)	0.0657 (7)
O1W	0.68093 (7)	0.6472 (2)	0.53876 (9)	0.0512 (5)
H1A	0.6718	0.6126	0.4983	0.077*
H1B	0.6757	0.5844	0.5679	0.077*
O2W	0.7500	0.7500	0.43813 (13)	0.0597 (8)
H2A	0.7658	0.8011	0.4125	0.090*
C1	0.56746 (13)	0.2553 (4)	0.46893 (18)	0.0675 (10)
H1	0.5792	0.2031	0.4345	0.081*
C2	0.56039 (16)	0.4160 (5)	0.5397 (3)	0.0967 (15)
H2	0.5651	0.4958	0.5653	0.116*
C3	0.52808 (14)	0.3172 (4)	0.5483 (2)	0.0817 (12)
H3	0.5059	0.3196	0.5804	0.098*
C4	0.55176 (11)	−0.2037 (3)	0.60003 (16)	0.0558 (8)
H4	0.5327	−0.2765	0.5869	0.067*
C5	0.60497 (13)	−0.0920 (4)	0.6489 (2)	0.0779 (11)
H5	0.6295	−0.0697	0.6753	0.094*
C6	0.58146 (12)	−0.0023 (4)	0.6111 (2)	0.0712 (10)
H6	0.5874	0.0938	0.6069	0.085*
C7	0.44988 (11)	0.0350 (4)	0.63811 (16)	0.0580 (8)
H7	0.4745	−0.0083	0.6579	0.070*
C8	0.38476 (13)	0.1312 (5)	0.6245 (2)	0.0810 (12)
H8	0.3560	0.1675	0.6318	0.097*
C9	0.40725 (12)	0.1289 (4)	0.56727 (19)	0.0736 (11)
H9	0.3962	0.1636	0.5280	0.088*
C10	0.71022 (13)	1.0575 (4)	0.58866 (18)	0.0663 (9)
H10	0.7140	1.0341	0.6323	0.080*
C11	0.69375 (15)	1.1776 (5)	0.5028 (2)	0.0842 (12)
H11	0.6844	1.2493	0.4749	0.101*
C12	0.70935 (15)	1.0492 (4)	0.4858 (2)	0.0819 (12)
H12	0.7125	1.0174	0.4432	0.098*
C20	0.65821 (10)	0.4142 (3)	0.31930 (14)	0.0459 (7)
C21	0.69273 (10)	0.3442 (4)	0.28942 (16)	0.0609 (9)
H21	0.7224	0.3681	0.2995	0.073*
C22	0.68436 (10)	0.2363 (4)	0.24350 (16)	0.0576 (9)
H22	0.7086	0.1916	0.2235	0.069*
C23	0.64154 (9)	0.1962 (3)	0.22789 (13)	0.0438 (6)
C24	0.60419 (9)	0.2703 (3)	0.25621 (13)	0.0406 (6)
C25	0.55847 (10)	0.2406 (3)	0.23935 (15)	0.0506 (7)
H25	0.5523	0.1678	0.2103	0.061*
C26	0.52392 (10)	0.3157 (4)	0.26466 (16)	0.0619 (9)
H26	0.4944	0.2929	0.2533	0.074*
C27	0.53196 (11)	0.4280 (4)	0.30797 (17)	0.0636 (9)
H27	0.5079	0.4804	0.3243	0.076*
C28	0.57517 (11)	0.4599 (3)	0.32607 (16)	0.0536 (8)
H28	0.5802	0.5339	0.3550	0.064*
C29	0.61259 (9)	0.3822 (3)	0.30145 (13)	0.0408 (6)
C30	0.67030 (11)	0.5228 (3)	0.37099 (15)	0.0523 (8)
C31	0.63602 (10)	0.0715 (3)	0.18193 (14)	0.0482 (7)
N9	0.7500	0.7500	0.64847 (19)	0.0789 (9)
N10	0.7681 (2)	0.7068 (7)	0.7487 (3)	0.0789 (9)	0.50
H10A	0.7842	0.7041	0.7834	0.095*	0.50
C13	0.78353 (16)	0.7509 (9)	0.6908 (2)	0.0789 (9)	0.50
H13	0.8131	0.7777	0.6819	0.095*	0.50
C14	0.7240 (2)	0.6669 (9)	0.7465 (3)	0.0789 (9)	0.50
H14	0.7053	0.6331	0.7794	0.095*	0.50
C15	0.71499 (17)	0.6904 (9)	0.6824 (3)	0.0789 (9)	0.50
H15	0.6874	0.6679	0.6633	0.095*	0.50

	U11	U22	U33	U12	U13	U23
Mn1	0.0469 (3)	0.0377 (4)	0.0398 (3)	0.0007 (3)	0.0026 (2)	0.0047 (3)
Mn2	0.0572 (4)	0.0383 (4)	0.0326 (3)	−0.0074 (3)	0.000	0.000
N1	0.0579 (15)	0.0432 (15)	0.0503 (15)	−0.0055 (12)	−0.0004 (12)	0.0041 (11)
N2	0.0686 (18)	0.0568 (19)	0.078 (2)	−0.0232 (15)	−0.0048 (16)	0.0047 (16)
N3	0.0525 (14)	0.0432 (15)	0.0498 (14)	0.0048 (11)	−0.0035 (11)	0.0045 (12)
N4	0.0600 (15)	0.0519 (17)	0.0560 (16)	0.0127 (13)	−0.0053 (13)	0.0106 (13)
N5	0.0556 (15)	0.0499 (15)	0.0506 (15)	0.0027 (12)	0.0090 (12)	0.0023 (12)
N6	0.0746 (18)	0.0633 (19)	0.0524 (16)	−0.0028 (15)	0.0200 (14)	−0.0069 (14)
N7	0.0631 (16)	0.0419 (15)	0.0637 (17)	−0.0015 (13)	0.0016 (13)	−0.0002 (13)
N8	0.0686 (18)	0.0457 (17)	0.092 (2)	0.0059 (14)	0.0175 (17)	−0.0035 (16)
O1	0.0891 (16)	0.0559 (14)	0.0509 (13)	−0.0123 (12)	0.0252 (12)	−0.0153 (11)
O2	0.0784 (15)	0.0518 (14)	0.0516 (13)	−0.0218 (12)	0.0107 (11)	−0.0151 (10)
O3	0.129 (2)	0.102 (2)	0.0540 (14)	−0.077 (2)	0.0049 (14)	−0.0151 (14)
O4	0.0837 (16)	0.0693 (16)	0.0441 (13)	−0.0292 (13)	0.0057 (11)	−0.0172 (11)
O1W	0.0607 (12)	0.0498 (13)	0.0431 (11)	−0.0133 (10)	0.0037 (9)	0.0033 (9)
O2W	0.082 (2)	0.065 (2)	0.0327 (14)	−0.0347 (17)	0.000	0.000
C1	0.080 (2)	0.056 (2)	0.066 (2)	−0.0206 (19)	0.0131 (19)	−0.0044 (18)
C2	0.106 (3)	0.059 (3)	0.125 (4)	−0.019 (2)	0.012 (3)	−0.031 (3)
C3	0.086 (3)	0.062 (2)	0.097 (3)	−0.013 (2)	0.020 (2)	−0.025 (2)
C4	0.0620 (19)	0.0449 (19)	0.061 (2)	−0.0002 (15)	−0.0067 (16)	0.0078 (15)
C5	0.076 (2)	0.061 (2)	0.097 (3)	0.003 (2)	−0.040 (2)	0.003 (2)
C6	0.073 (2)	0.047 (2)	0.093 (3)	−0.0006 (17)	−0.028 (2)	0.0060 (19)
C7	0.0611 (19)	0.065 (2)	0.0476 (18)	0.0006 (16)	0.0089 (15)	−0.0035 (16)
C8	0.067 (2)	0.091 (3)	0.085 (3)	0.021 (2)	0.025 (2)	0.000 (2)
C9	0.070 (2)	0.083 (3)	0.069 (2)	0.025 (2)	0.0110 (18)	0.013 (2)
C10	0.087 (3)	0.045 (2)	0.067 (2)	0.0017 (18)	0.0127 (19)	−0.0015 (17)
C11	0.097 (3)	0.065 (3)	0.091 (3)	0.026 (2)	−0.004 (2)	0.012 (2)
C12	0.112 (3)	0.067 (3)	0.067 (2)	0.024 (2)	−0.012 (2)	0.003 (2)
C20	0.0513 (16)	0.0452 (17)	0.0412 (15)	−0.0115 (13)	−0.0016 (12)	−0.0077 (13)
C21	0.0435 (16)	0.075 (2)	0.064 (2)	−0.0141 (16)	0.0012 (15)	−0.0213 (18)
C22	0.0449 (16)	0.068 (2)	0.0602 (19)	−0.0042 (15)	0.0068 (14)	−0.0221 (17)
C23	0.0480 (15)	0.0454 (16)	0.0381 (14)	−0.0061 (13)	0.0019 (12)	−0.0092 (13)
C24	0.0451 (14)	0.0417 (16)	0.0349 (14)	−0.0035 (12)	−0.0039 (11)	−0.0011 (12)
C25	0.0477 (16)	0.0563 (19)	0.0478 (16)	−0.0046 (14)	−0.0075 (13)	−0.0063 (15)
C26	0.0437 (17)	0.081 (2)	0.061 (2)	0.0022 (16)	−0.0135 (15)	−0.0003 (19)
C27	0.0534 (18)	0.073 (2)	0.065 (2)	0.0204 (17)	−0.0030 (16)	−0.0065 (18)
C28	0.0619 (19)	0.0467 (18)	0.0523 (18)	0.0082 (15)	−0.0063 (15)	−0.0082 (14)
C29	0.0477 (15)	0.0372 (15)	0.0376 (14)	−0.0013 (12)	−0.0026 (11)	−0.0007 (12)
C30	0.0614 (18)	0.0502 (19)	0.0452 (18)	−0.0130 (15)	−0.0087 (14)	−0.0049 (14)
C31	0.0528 (16)	0.0450 (18)	0.0468 (17)	−0.0051 (14)	−0.0005 (13)	−0.0089 (13)
N9	0.101 (2)	0.087 (2)	0.0486 (13)	0.0064 (19)	0.000	0.000
N10	0.101 (2)	0.087 (2)	0.0486 (13)	0.0064 (19)	0.000	0.000
C13	0.101 (2)	0.087 (2)	0.0486 (13)	0.0064 (19)	0.000	0.000
C14	0.101 (2)	0.087 (2)	0.0486 (13)	0.0064 (19)	0.000	0.000
C15	0.101 (2)	0.087 (2)	0.0486 (13)	0.0064 (19)	0.000	0.000

Mn1—N1i	2.250 (3)	C4—H4	0.9300
Mn1—N1	2.250 (3)	C5—C6	1.344 (5)
Mn1—N3i	2.271 (2)	C5—H5	0.9300
Mn1—N3	2.271 (2)	C6—H6	0.9300
Mn1—N5i	2.276 (2)	C7—H7	0.9300
Mn1—N5	2.276 (2)	C8—C9	1.351 (5)
Mn2—N7ii	2.283 (3)	C8—H8	0.9300
Mn2—N7	2.283 (3)	C9—H9	0.9300
Mn2—N9	2.190 (4)	C10—H10	0.9300
Mn2—O1Wii	2.265 (2)	C11—C12	1.346 (6)
Mn2—O1W	2.265 (2)	C11—H11	0.9300
Mn2—O2W	2.129 (3)	C12—H12	0.9300
N1—C1	1.302 (4)	C20—C21	1.363 (4)
N1—C3	1.352 (4)	C20—C29	1.432 (4)
N2—C1	1.316 (4)	C20—C30	1.521 (4)
N2—C2	1.335 (5)	C21—C22	1.412 (4)
N2—H2N	0.8600	C21—H21	0.9300
N3—C4	1.314 (4)	C22—C23	1.362 (4)
N3—C6	1.360 (4)	C22—H22	0.9300
N4—C4	1.327 (4)	C23—C24	1.433 (4)
N4—C5	1.356 (5)	C23—C31	1.520 (4)
N4—H4N	0.8600	C24—C25	1.425 (4)
N5—C7	1.319 (4)	C24—C29	1.430 (4)
N5—C9	1.355 (4)	C25—C26	1.350 (4)
N6—C7	1.330 (4)	C25—H25	0.9300
N6—C8	1.355 (5)	C26—C27	1.406 (5)
N6—H6N	0.8600	C26—H26	0.9300
N7—C10	1.312 (4)	C27—C28	1.366 (5)
N7—C12	1.372 (5)	C27—H27	0.9300
N8—C10	1.335 (5)	C28—C29	1.423 (4)
N8—C11	1.342 (5)	C28—H28	0.9300
N8—H8N	0.8600	N9—C13	1.3195 (10)
O1—C31	1.248 (3)	N9—C13ii	1.3195 (10)
O2—C31	1.262 (4)	N9—C15ii	1.3703 (10)
O3—C30	1.239 (4)	N9—C15	1.3703 (10)
O4—C30	1.230 (4)	N10—C13	1.3400 (10)
O1W—H1A	0.9331	N10—C14	1.3597 (11)
O1W—H1B	0.8576	N10—H10A	0.8600
O2W—H2A	0.8542	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.3603 (11)
C2—C3	1.349 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—H3	0.9300
N1i—Mn1—N1	180.00 (12)	C5—C6—N3	110.1 (3)
N1i—Mn1—N3i	88.89 (9)	C5—C6—H6	124.9
N1—Mn1—N3i	91.11 (9)	N3—C6—H6	124.9
N1i—Mn1—N3	91.11 (9)	N5—C7—N6	112.2 (3)
N1—Mn1—N3	88.89 (9)	N5—C7—H7	123.9
N3i—Mn1—N3	180.00 (8)	N6—C7—H7	123.9
N1i—Mn1—N5i	90.80 (9)	C9—C8—N6	106.8 (3)
N1—Mn1—N5i	89.20 (9)	C9—C8—H8	126.6
N3i—Mn1—N5i	90.60 (9)	N6—C8—H8	126.6
N3—Mn1—N5i	89.40 (9)	C8—C9—N5	109.7 (3)
N1i—Mn1—N5	89.20 (9)	C8—C9—H9	125.2
N1—Mn1—N5	90.80 (9)	N5—C9—H9	125.2
N3i—Mn1—N5	89.40 (9)	N7—C10—N8	112.4 (3)
N3—Mn1—N5	90.60 (9)	N7—C10—H10	123.8
N5i—Mn1—N5	180.00 (9)	N8—C10—H10	123.8
O2W—Mn2—N9	180.000 (1)	N8—C11—C12	106.4 (4)
O2W—Mn2—O1Wii	88.42 (5)	N8—C11—H11	126.8
N9—Mn2—O1Wii	91.58 (5)	C12—C11—H11	126.8
O2W—Mn2—O1W	88.42 (5)	C11—C12—N7	110.2 (4)
N9—Mn2—O1W	91.58 (5)	C11—C12—H12	124.9
O1Wii—Mn2—O1W	176.85 (10)	N7—C12—H12	124.9
O2W—Mn2—N7ii	89.24 (7)	C21—C20—C29	119.3 (3)
N9—Mn2—N7ii	90.76 (7)	C21—C20—C30	117.8 (3)
O1Wii—Mn2—N7ii	92.42 (9)	C29—C20—C30	122.9 (3)
O1W—Mn2—N7ii	87.54 (9)	C20—C21—C22	121.3 (3)
O2W—Mn2—N7	89.24 (7)	C20—C21—H21	119.3
N9—Mn2—N7	90.76 (7)	C22—C21—H21	119.3
O1Wii—Mn2—N7	87.54 (9)	C23—C22—C21	121.5 (3)
O1W—Mn2—N7	92.42 (9)	C23—C22—H22	119.3
N7ii—Mn2—N7	178.48 (14)	C21—C22—H22	119.3
C1—N1—C3	103.8 (3)	C22—C23—C24	119.1 (3)
C1—N1—Mn1	126.4 (2)	C22—C23—C31	117.6 (3)
C3—N1—Mn1	128.6 (2)	C24—C23—C31	123.3 (2)
C1—N2—C2	105.8 (3)	C25—C24—C29	118.0 (3)
C1—N2—H2N	127.1	C25—C24—C23	122.5 (3)
C2—N2—H2N	127.1	C29—C24—C23	119.4 (2)
C4—N3—C6	104.3 (3)	C26—C25—C24	121.5 (3)
C4—N3—Mn1	124.7 (2)	C26—C25—H25	119.3
C6—N3—Mn1	130.6 (2)	C24—C25—H25	119.3
C4—N4—C5	106.3 (3)	C25—C26—C27	120.9 (3)
C4—N4—H4N	126.9	C25—C26—H26	119.6
C5—N4—H4N	126.9	C27—C26—H26	119.6
C7—N5—C9	104.9 (3)	C28—C27—C26	119.9 (3)
C7—N5—Mn1	124.8 (2)	C28—C27—H27	120.1
C9—N5—Mn1	129.4 (2)	C26—C27—H27	120.1
C7—N6—C8	106.4 (3)	C27—C28—C29	121.2 (3)
C7—N6—H6N	126.8	C27—C28—H28	119.4
C8—N6—H6N	126.8	C29—C28—H28	119.4
C10—N7—C12	103.9 (3)	C28—C29—C24	118.6 (3)
C10—N7—Mn2	130.0 (2)	C28—C29—C20	122.3 (3)
C12—N7—Mn2	126.1 (2)	C24—C29—C20	119.1 (2)
C10—N8—C11	107.1 (3)	O4—C30—O3	123.9 (3)
C10—N8—H8N	126.5	O4—C30—C20	119.4 (3)
C11—N8—H8N	126.5	O3—C30—C20	116.7 (3)
Mn2—O1W—H1A	116.0	O1—C31—O2	125.1 (3)
Mn2—O1W—H1B	116.3	O1—C31—C23	117.6 (3)
H1A—O1W—H1B	109.0	O2—C31—C23	117.3 (3)
Mn2—O2W—H2A	128.0	C13—N9—C15	103.7 (4)
N1—C1—N2	113.7 (3)	C13—N9—Mn2	131.2 (3)
N1—C1—H1	123.1	C15—N9—Mn2	120.6 (3)
N2—C1—H1	123.1	C13—N10—C14	112.6 (6)
N2—C2—C3	107.0 (4)	C13—N10—H10A	123.7
N2—C2—H2	126.5	C14—N10—H10A	123.7
C3—C2—H2	126.5	N9—C13—N10	109.0 (5)
C2—C3—N1	109.5 (4)	N9—C13—H13	125.5
C2—C3—H3	125.2	N10—C13—H13	125.5
N1—C3—H3	125.2	N10—C14—C15	100.0 (6)
N3—C4—N4	112.7 (3)	N10—C14—H14	130.0
N3—C4—H4	123.6	C15—C14—H14	130.0
N4—C4—H4	123.6	C14—C15—N9	114.3 (5)
C6—C5—N4	106.6 (3)	C14—C15—H15	122.9
C6—C5—H5	126.7	N9—C15—H15	122.9
N4—C5—H5	126.7

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4	0.93	1.85	2.772 (3)	170
O1W—H1B···O1iii	0.86	2.02	2.875 (3)	175
O2W—H2A···O3ii	0.85	1.78	2.624 (3)	172
N2—H2N···O4	0.86	1.87	2.730 (4)	176
N4—H4N···O2iv	0.86	1.91	2.765 (3)	177
N6—H6N···O2i	0.86	1.95	2.810 (4)	178
N8—H8N···O1v	0.86	2.02	2.870 (4)	167
N10—H10A···O3vi	0.86	1.78	2.560 (7)	150

Table 1

Selected bond lengths (Å)

Mn1—N1	2.250 (3)
Mn1—N3	2.271 (2)
Mn1—N5	2.276 (2)
Mn2—N7	2.283 (3)
Mn2—N9	2.190 (4)
Mn2—O1W	2.265 (2)
Mn2—O2W	2.129 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O4	0.93	1.85	2.772 (3)	170
O1W—H1B⋯O1i	0.86	2.02	2.875 (3)	175
O2W—H2A⋯O3ii	0.85	1.78	2.624 (3)	172
N2—H2N⋯O4	0.86	1.87	2.730 (4)	176
N4—H4N⋯O2iii	0.86	1.91	2.765 (3)	177
N6—H6N⋯O2iv	0.86	1.95	2.810 (4)	178
N8—H8N⋯O1v	0.86	2.02	2.870 (4)	167
N10—H10A⋯O3vi	0.86	1.78	2.560 (7)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .