Poly[diaqua-(μ(4)-2,5-dicarb-oxy-benzene-1,4-dicarboxyl-ato-κ(4)O(1):O(2):O(4):O(5))(μ(2)-2,5-dicarb-oxy-benzene-1,4-dicarboxyl-ato-κ(2)O(1):O(4))bis-(1,10-phenanthroline-κ(2)N,N')dimanganese(II)].

In the title compound, [Mn(2)(C(10)H(4)O(8))(2)(C(12)H(8)N(2))(2)(H(2)O)(2)](n), the Mn(2+) ion has a slightly distorted octa-hedral N(2)O(4) coordination geometry being coordinated by one aqua O atom, two N atoms of the chelating 1,10-phenanthroline ligand and three carboxyl O atoms from three 2,5-dicarb-oxy-benzene-1,4-dicarboxyl-ate (H(2)btec(2-)) ligands. The H(2)btec(2-) anion exhibits two different coordination modes, viz. μ(2) and μ(4). Both of the H(2)btec(2-) anions are located on special positions (inversion centers). The μ(4)-anion bridges adjacent Mn(II) atoms, forming a chain along the a axis. Adjacent chains are further bridged by μ(2)-anions, resulting in a two-dimensional layered polymer parallel to (011). In the crystal, extensive carb-oxy-carboxyl-ate O-H⋯O and water-carboxyl-ate O-H⋯O inter-actions lead to the formation of a three-dimensional supra-molecular network.

Related literature

For isotypic structures, see: Hu et al. (2004 ▶); Yu et al. (2007 ▶). For background to manganese complexes and phenanthroline complexes, see: Zhu et al. (2006 ▶); Zhong et al. (2009 ▶); Cui et al. (2010 ▶); Zhong (2011 ▶). For background to coordination polymers, see: Batten & Robson (1998 ▶); Fabelo et al. (2008 ▶); Liu et al. (2007 ▶); Li et al. (2003 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Mn2(C10H4O8)2(C12H8N2)2(H2O)2]

M = 1010.58

Triclinic,

a = 9.880 (2) Å

b = 10.246 (2) Å

c = 11.272 (2) Å

α = 86.29 (3)°

β = 71.82 (3)°

γ = 65.32 (3)°

V = 982.2 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.74 mm−1

T = 223 K

0.50 × 0.50 × 0.30 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB: Jacobson, 1998 ▶) T min = 0.710, T max = 0.810

9376 measured reflections

4403 independent reflections

3757 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.05

4403 reflections

315 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035441/zq2172sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035441/zq2172Isup2.hkl

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

[Mn2(C10H4O8)2(C12H8N2)2(H2O)2]	Z = 1
Mr = 1010.58	F(000) = 514
Triclinic, P1	Dx = 1.708 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.880 (2) Å	Cell parameters from 4733 reflections
b = 10.246 (2) Å	θ = 3.5–27.5°
c = 11.272 (2) Å	µ = 0.74 mm−1
α = 86.29 (3)°	T = 223 K
β = 71.82 (3)°	Prism, pale yellow
γ = 65.32 (3)°	0.50 × 0.50 × 0.30 mm
V = 982.2 (5) Å3

Rigaku Mercury CCD diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	3757 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.025
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −11→12
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −12→13
Tmin = 0.710, Tmax = 0.810	l = −13→14
9376 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0441P)2] where P = (Fo2 + 2Fc2)/3
4403 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.45 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	0.03585 (3)	0.13877 (2)	0.76264 (2)	0.01653 (9)
O1	−0.07365 (14)	0.18231 (12)	0.61328 (10)	0.0203 (2)
O1W	0.19967 (17)	−0.06467 (13)	0.65855 (13)	0.0287 (3)
H1WB	0.235 (3)	−0.112 (2)	0.709 (2)	0.048 (7)*
H1WA	0.191 (3)	−0.113 (2)	0.610 (2)	0.051 (7)*
O2	−0.20089 (15)	0.27574 (12)	0.47561 (11)	0.0251 (3)
O3	−0.36828 (15)	0.48967 (13)	0.70890 (11)	0.0289 (3)
O4	−0.38216 (15)	0.71264 (12)	0.71302 (12)	0.0344 (3)
H4	−0.4697	0.7305	0.7625	0.052*
O5	−0.16064 (13)	−0.06578 (11)	1.09959 (10)	0.0196 (2)
O6	−0.32453 (13)	0.16588 (11)	1.15378 (10)	0.0201 (2)
O7	−0.15899 (14)	0.08266 (12)	0.86097 (10)	0.0230 (3)
O8	−0.24706 (16)	0.05474 (14)	0.70863 (10)	0.0302 (3)
H8	−0.1745	0.0730	0.6647	0.045*
N1	−0.10378 (17)	0.35804 (14)	0.86211 (12)	0.0201 (3)
N2	0.19008 (17)	0.25423 (14)	0.69255 (12)	0.0200 (3)
C1	−0.2460 (2)	0.40702 (19)	0.94468 (16)	0.0277 (4)
H1A	−0.2977	0.3468	0.9626	0.033*
C2	−0.3227 (3)	0.5448 (2)	1.00651 (18)	0.0380 (5)
H2A	−0.4231	0.5759	1.0636	0.046*
C3	−0.2453 (3)	0.63274 (19)	0.98044 (18)	0.0389 (5)
H3A	−0.2940	0.7250	1.0199	0.047*
C4	−0.0943 (2)	0.58473 (18)	0.89512 (16)	0.0298 (4)
C5	−0.0026 (3)	0.6674 (2)	0.86821 (19)	0.0396 (5)
H5A	−0.0461	0.7597	0.9068	0.048*
C6	0.1431 (3)	0.6146 (2)	0.78925 (19)	0.0394 (5)
H6A	0.1996	0.6706	0.7747	0.047*
C7	0.2162 (2)	0.4723 (2)	0.72534 (16)	0.0298 (4)
C8	0.3693 (3)	0.4120 (2)	0.64430 (18)	0.0376 (5)
H8A	0.4301	0.4641	0.6276	0.045*
C9	0.4304 (2)	0.2758 (2)	0.58920 (19)	0.0386 (5)
H9A	0.5329	0.2340	0.5354	0.046*
C10	0.3351 (2)	0.2004 (2)	0.61544 (17)	0.0289 (4)
H10A	0.3762	0.1085	0.5768	0.035*
C11	0.1296 (2)	0.38922 (17)	0.74896 (15)	0.0211 (4)
C12	−0.0266 (2)	0.44510 (17)	0.83610 (15)	0.0212 (4)
C13	0.08667 (19)	0.36364 (16)	0.44035 (14)	0.0169 (3)
H13A	0.1458	0.2719	0.3997	0.020*
C14	−0.06214 (19)	0.39624 (16)	0.52328 (13)	0.0152 (3)
C15	−0.15027 (19)	0.53453 (16)	0.58379 (14)	0.0161 (3)
C16	−0.39312 (18)	0.02498 (15)	1.04387 (13)	0.0144 (3)
C17	−0.37723 (18)	0.02458 (15)	0.91572 (14)	0.0149 (3)
C18	−0.48391 (18)	−0.00020 (15)	0.87421 (13)	0.0156 (3)
H16A	−0.4723	−0.0001	0.7891	0.019*
C19	−0.12121 (19)	0.27874 (16)	0.53878 (13)	0.0159 (3)
C20	−0.3108 (2)	0.57403 (17)	0.67429 (14)	0.0190 (3)
C21	−0.28096 (18)	0.04445 (16)	1.10044 (13)	0.0149 (3)
C22	−0.25052 (19)	0.05606 (16)	0.82447 (14)	0.0168 (3)

	U11	U22	U33	U12	U13	U23
Mn1	0.01545 (15)	0.01648 (14)	0.02046 (14)	−0.00844 (11)	−0.00689 (10)	0.00152 (9)
O1	0.0245 (7)	0.0232 (6)	0.0220 (6)	−0.0159 (5)	−0.0120 (5)	0.0094 (5)
O1W	0.0373 (9)	0.0203 (6)	0.0300 (7)	−0.0062 (6)	−0.0199 (6)	−0.0032 (6)
O2	0.0358 (8)	0.0259 (6)	0.0276 (6)	−0.0192 (6)	−0.0205 (6)	0.0070 (5)
O3	0.0233 (7)	0.0290 (6)	0.0343 (7)	−0.0167 (6)	0.0000 (6)	−0.0006 (5)
O4	0.0216 (7)	0.0234 (6)	0.0446 (8)	−0.0094 (6)	0.0095 (6)	−0.0094 (6)
O5	0.0162 (6)	0.0204 (6)	0.0216 (6)	−0.0043 (5)	−0.0095 (5)	−0.0006 (4)
O6	0.0176 (6)	0.0187 (6)	0.0255 (6)	−0.0074 (5)	−0.0079 (5)	−0.0029 (5)
O7	0.0228 (7)	0.0365 (7)	0.0204 (6)	−0.0216 (6)	−0.0092 (5)	0.0078 (5)
O8	0.0372 (8)	0.0556 (8)	0.0172 (6)	−0.0376 (7)	−0.0102 (5)	0.0109 (5)
N1	0.0202 (8)	0.0203 (7)	0.0195 (7)	−0.0068 (6)	−0.0082 (6)	0.0016 (5)
N2	0.0200 (8)	0.0213 (7)	0.0218 (7)	−0.0109 (6)	−0.0079 (6)	0.0041 (5)
C1	0.0222 (10)	0.0311 (9)	0.0241 (8)	−0.0055 (8)	−0.0072 (7)	−0.0014 (7)
C2	0.0318 (12)	0.0358 (11)	0.0286 (10)	0.0032 (9)	−0.0086 (9)	−0.0069 (8)
C3	0.0505 (14)	0.0212 (9)	0.0299 (10)	0.0043 (9)	−0.0186 (10)	−0.0056 (8)
C4	0.0493 (13)	0.0180 (8)	0.0249 (9)	−0.0098 (8)	−0.0217 (9)	0.0030 (7)
C5	0.0750 (18)	0.0220 (9)	0.0355 (11)	−0.0236 (11)	−0.0320 (12)	0.0078 (8)
C6	0.0758 (18)	0.0343 (10)	0.0394 (11)	−0.0414 (12)	−0.0366 (12)	0.0188 (9)
C7	0.0478 (13)	0.0364 (10)	0.0284 (9)	−0.0322 (10)	−0.0249 (9)	0.0169 (8)
C8	0.0450 (13)	0.0556 (13)	0.0389 (11)	−0.0404 (11)	−0.0245 (10)	0.0220 (10)
C9	0.0246 (11)	0.0605 (14)	0.0360 (10)	−0.0250 (10)	−0.0091 (9)	0.0158 (10)
C10	0.0230 (10)	0.0335 (10)	0.0291 (9)	−0.0128 (8)	−0.0063 (8)	0.0066 (8)
C11	0.0299 (10)	0.0228 (8)	0.0201 (8)	−0.0158 (8)	−0.0149 (7)	0.0074 (6)
C12	0.0304 (10)	0.0165 (8)	0.0198 (8)	−0.0084 (7)	−0.0145 (7)	0.0038 (6)
C13	0.0190 (9)	0.0149 (7)	0.0179 (7)	−0.0075 (6)	−0.0064 (6)	0.0006 (6)
C14	0.0179 (9)	0.0176 (7)	0.0146 (7)	−0.0097 (6)	−0.0082 (6)	0.0040 (6)
C15	0.0163 (8)	0.0184 (8)	0.0150 (7)	−0.0076 (6)	−0.0063 (6)	0.0024 (6)
C16	0.0143 (8)	0.0121 (7)	0.0181 (7)	−0.0055 (6)	−0.0067 (6)	0.0007 (6)
C17	0.0139 (8)	0.0144 (7)	0.0172 (7)	−0.0066 (6)	−0.0049 (6)	0.0022 (6)
C18	0.0167 (9)	0.0168 (7)	0.0142 (7)	−0.0073 (6)	−0.0057 (6)	0.0021 (6)
C19	0.0159 (9)	0.0166 (7)	0.0137 (7)	−0.0076 (6)	−0.0015 (6)	−0.0004 (6)
C20	0.0175 (9)	0.0222 (8)	0.0182 (7)	−0.0087 (7)	−0.0061 (7)	0.0003 (6)
C21	0.0147 (8)	0.0193 (8)	0.0133 (7)	−0.0101 (7)	−0.0038 (6)	0.0025 (6)
C22	0.0166 (9)	0.0171 (7)	0.0186 (7)	−0.0087 (7)	−0.0061 (6)	0.0033 (6)

Mn1—O1W	2.1576 (17)	C4—C12	1.408 (2)
Mn1—O5i	2.1830 (12)	C4—C5	1.437 (3)
Mn1—O7	2.1852 (13)	C5—C6	1.331 (3)
Mn1—O1	2.2001 (12)	C5—H5A	0.9300
Mn1—N2	2.2314 (14)	C6—C7	1.448 (3)
Mn1—N1	2.2317 (17)	C6—H6A	0.9300
O1—C19	1.2858 (19)	C7—C8	1.391 (3)
O1W—H1WB	0.79 (2)	C7—C11	1.402 (2)
O1W—H1WA	0.80 (2)	C8—C9	1.368 (3)
O2—C19	1.2250 (19)	C8—H8A	0.9300
O3—C20	1.2040 (19)	C9—C10	1.405 (3)
O4—C20	1.325 (2)	C9—H9A	0.9300
O4—H4	0.8200	C10—H10A	0.9300
O5—C21	1.250 (2)	C11—C12	1.437 (3)
O5—Mn1i	2.1830 (12)	C13—C14	1.385 (2)
O6—C21	1.2581 (18)	C13—C15ii	1.400 (2)
O7—C22	1.2304 (19)	C13—H13A	0.9300
O8—C22	1.2963 (18)	C14—C15	1.398 (2)
O8—H8	0.8200	C14—C19	1.522 (2)
N1—C1	1.322 (2)	C15—C13ii	1.400 (2)
N1—C12	1.363 (2)	C15—C20	1.493 (2)
N2—C10	1.318 (2)	C16—C18iii	1.386 (2)
N2—C11	1.364 (2)	C16—C17	1.404 (2)
C1—C2	1.399 (3)	C16—C21	1.522 (2)
C1—H1A	0.9300	C17—C18	1.393 (2)
C2—C3	1.372 (3)	C17—C22	1.490 (2)
C2—H2A	0.9300	C18—C16iii	1.386 (2)
C3—C4	1.395 (3)	C18—H16A	0.9300
C3—H3A	0.9300
O1W—Mn1—O5i	85.93 (5)	C8—C7—C6	123.54 (17)
O1W—Mn1—O7	99.43 (6)	C11—C7—C6	118.32 (19)
O5i—Mn1—O7	96.43 (5)	C9—C8—C7	119.84 (17)
O1W—Mn1—O1	86.66 (6)	C9—C8—H8A	120.1
O5i—Mn1—O1	172.36 (4)	C7—C8—H8A	120.1
O7—Mn1—O1	82.92 (4)	C8—C9—C10	118.7 (2)
O1W—Mn1—N2	96.43 (6)	C8—C9—H9A	120.6
O5i—Mn1—N2	84.21 (5)	C10—C9—H9A	120.6
O7—Mn1—N2	164.13 (5)	N2—C10—C9	122.82 (18)
O1—Mn1—N2	98.51 (5)	N2—C10—H10A	118.6
O1W—Mn1—N1	171.56 (5)	C9—C10—H10A	118.6
O5i—Mn1—N1	91.39 (5)	N2—C11—C7	121.88 (17)
O7—Mn1—N1	88.81 (6)	N2—C11—C12	118.21 (14)
O1—Mn1—N1	96.21 (5)	C7—C11—C12	119.90 (16)
N2—Mn1—N1	75.32 (6)	N1—C12—C4	121.70 (17)
C19—O1—Mn1	141.94 (10)	N1—C12—C11	118.23 (14)
Mn1—O1W—H1WB	103.6 (17)	C4—C12—C11	120.05 (16)
Mn1—O1W—H1WA	131.1 (18)	C14—C13—C15ii	121.62 (14)
H1WB—O1W—H1WA	111 (2)	C14—C13—H13A	119.2
C20—O4—H4	109.5	C15ii—C13—H13A	119.2
C21—O5—Mn1i	131.34 (10)	C13—C14—C15	118.80 (14)
C22—O7—Mn1	132.25 (10)	C13—C14—C19	117.00 (13)
C22—O8—H8	109.5	C15—C14—C19	124.16 (14)
C1—N1—C12	118.72 (15)	C14—C15—C13ii	119.58 (15)
C1—N1—Mn1	127.15 (12)	C14—C15—C20	120.56 (14)
C12—N1—Mn1	114.05 (11)	C13ii—C15—C20	119.85 (14)
C10—N2—C11	118.60 (15)	C18iii—C16—C17	118.29 (14)
C10—N2—Mn1	126.98 (11)	C18iii—C16—C21	116.70 (12)
C11—N2—Mn1	113.96 (11)	C17—C16—C21	124.95 (14)
N1—C1—C2	123.36 (18)	C18—C17—C16	119.83 (14)
N1—C1—H1A	118.3	C18—C17—C22	119.82 (13)
C2—C1—H1A	118.3	C16—C17—C22	120.31 (14)
C3—C2—C1	118.06 (19)	C16iii—C18—C17	121.88 (13)
C3—C2—H2A	121.0	C16iii—C18—H16A	119.1
C1—C2—H2A	121.0	C17—C18—H16A	119.1
C2—C3—C4	120.50 (17)	O2—C19—O1	124.21 (14)
C2—C3—H3A	119.8	O2—C19—C14	119.47 (13)
C4—C3—H3A	119.8	O1—C19—C14	116.15 (13)
C3—C4—C12	117.66 (17)	O3—C20—O4	123.94 (16)
C3—C4—C5	123.69 (17)	O3—C20—C15	123.99 (15)
C12—C4—C5	118.61 (19)	O4—C20—C15	112.06 (13)
C6—C5—C4	121.33 (18)	O5—C21—O6	125.93 (14)
C6—C5—H5A	119.3	O5—C21—C16	116.50 (13)
C4—C5—H5A	119.3	O6—C21—C16	117.22 (14)
C5—C6—C7	121.77 (17)	O7—C22—O8	124.29 (14)
C5—C6—H6A	119.1	O7—C22—C17	120.20 (13)
C7—C6—H6A	119.1	O8—C22—C17	115.50 (14)
C8—C7—C11	118.12 (17)
O1W—Mn1—O1—C19	−130.08 (17)	C6—C7—C11—N2	−179.99 (15)
O7—Mn1—O1—C19	129.98 (17)	C8—C7—C11—C12	177.39 (15)
N2—Mn1—O1—C19	−34.06 (17)	C6—C7—C11—C12	−0.9 (2)
N1—Mn1—O1—C19	41.96 (17)	C1—N1—C12—C4	0.2 (2)
O1W—Mn1—O7—C22	−69.40 (15)	Mn1—N1—C12—C4	−176.96 (12)
O5i—Mn1—O7—C22	−156.33 (14)	C1—N1—C12—C11	178.22 (14)
O1—Mn1—O7—C22	16.00 (14)	Mn1—N1—C12—C11	1.03 (18)
N2—Mn1—O7—C22	112.2 (2)	C3—C4—C12—N1	−1.0 (2)
N1—Mn1—O7—C22	112.41 (15)	C5—C4—C12—N1	176.62 (15)
O5i—Mn1—N1—C1	−95.99 (14)	C3—C4—C12—C11	−178.99 (15)
O7—Mn1—N1—C1	0.42 (14)	C5—C4—C12—C11	−1.3 (2)
O1—Mn1—N1—C1	83.16 (14)	N2—C11—C12—N1	2.8 (2)
N2—Mn1—N1—C1	−179.63 (15)	C7—C11—C12—N1	−176.29 (14)
O5i—Mn1—N1—C12	80.91 (11)	N2—C11—C12—C4	−179.13 (14)
O7—Mn1—N1—C12	177.32 (11)	C7—C11—C12—C4	1.7 (2)
O1—Mn1—N1—C12	−99.93 (11)	C15ii—C13—C14—C15	0.1 (2)
N2—Mn1—N1—C12	−2.73 (10)	C15ii—C13—C14—C19	177.97 (13)
O1W—Mn1—N2—C10	−2.02 (15)	C13—C14—C15—C13ii	−0.1 (2)
O5i—Mn1—N2—C10	83.21 (14)	C19—C14—C15—C13ii	−177.80 (13)
O7—Mn1—N2—C10	176.37 (15)	C13—C14—C15—C20	−179.72 (13)
O1—Mn1—N2—C10	−89.58 (15)	C19—C14—C15—C20	2.6 (2)
N1—Mn1—N2—C10	176.18 (15)	C18iii—C16—C17—C18	0.1 (2)
O1W—Mn1—N2—C11	−174.03 (11)	C21—C16—C17—C18	177.34 (13)
O5i—Mn1—N2—C11	−88.80 (11)	C18iii—C16—C17—C22	177.73 (13)
O7—Mn1—N2—C11	4.4 (2)	C21—C16—C17—C22	−5.0 (2)
O1—Mn1—N2—C11	98.40 (11)	C16—C17—C18—C16iii	−0.1 (2)
N1—Mn1—N2—C11	4.17 (10)	C22—C17—C18—C16iii	−177.74 (14)
C12—N1—C1—C2	0.6 (3)	Mn1—O1—C19—O2	−168.79 (11)
Mn1—N1—C1—C2	177.34 (13)	Mn1—O1—C19—C14	16.0 (2)
N1—C1—C2—C3	−0.5 (3)	C13—C14—C19—O2	−93.97 (19)
C1—C2—C3—C4	−0.4 (3)	C15—C14—C19—O2	83.76 (19)
C2—C3—C4—C12	1.1 (3)	C13—C14—C19—O1	81.52 (17)
C2—C3—C4—C5	−176.44 (17)	C15—C14—C19—O1	−100.75 (18)
C3—C4—C5—C6	177.60 (18)	C14—C15—C20—O3	6.7 (2)
C12—C4—C5—C6	0.1 (3)	C13ii—C15—C20—O3	−172.92 (15)
C4—C5—C6—C7	0.8 (3)	C14—C15—C20—O4	−173.91 (14)
C5—C6—C7—C8	−178.54 (18)	C13ii—C15—C20—O4	6.5 (2)
C5—C6—C7—C11	−0.4 (3)	Mn1i—O5—C21—O6	31.1 (2)
C11—C7—C8—C9	0.8 (3)	Mn1i—O5—C21—C16	−141.87 (11)
C6—C7—C8—C9	178.96 (17)	C18iii—C16—C21—O5	93.87 (17)
C7—C8—C9—C10	0.6 (3)	C17—C16—C21—O5	−83.45 (18)
C11—N2—C10—C9	0.2 (3)	C18iii—C16—C21—O6	−79.70 (17)
Mn1—N2—C10—C9	−171.46 (13)	C17—C16—C21—O6	102.98 (18)
C8—C9—C10—N2	−1.1 (3)	Mn1—O7—C22—O8	0.8 (2)
C10—N2—C11—C7	1.2 (2)	Mn1—O7—C22—C17	−178.26 (10)
Mn1—N2—C11—C7	173.95 (12)	C18—C17—C22—O7	177.64 (14)
C10—N2—C11—C12	−177.90 (15)	C16—C17—C22—O7	0.0 (2)
Mn1—N2—C11—C12	−5.16 (18)	C18—C17—C22—O8	−1.5 (2)
C8—C7—C11—N2	−1.7 (2)	C16—C17—C22—O8	−179.20 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O1	0.82	1.75	2.5176 (16)	155
O4—H4···O6iv	0.82	1.81	2.592 (2)	158
O1W—H1WB···O6i	0.79 (2)	1.95 (3)	2.7108 (19)	160 (2)
O1W—H1WA···O2v	0.80 (2)	1.94 (2)	2.7117 (18)	162 (2)

Table 1

Selected bond lengths (Å)

Mn1—O1W	2.1576 (17)
Mn1—O5i	2.1830 (12)
Mn1—O7	2.1852 (13)
Mn1—O1	2.2001 (12)
Mn1—N2	2.2314 (14)
Mn1—N1	2.2317 (17)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O1	0.82	1.75	2.5176 (16)	155
O4—H4⋯O6ii	0.82	1.81	2.592 (2)	158
O1W—H1WB⋯O6i	0.79 (2)	1.95 (3)	2.7108 (19)	160 (2)
O1W—H1WA⋯O2iii	0.80 (2)	1.94 (2)	2.7117 (18)	162 (2)

Symmetry codes: (i) ; (ii) ; (iii) .