catena-Poly[[[aqua-(1,10-phenanthroline-κ(2)N,N')manganese(II)]-{μ-4,4'-[(4-carb-oxy-benz-yl)nitrilo]-dibenzoato-κ(4)O,O':O'',O'''}] monohydrate].

The title compound, {[Mn(C(22)H(15)NO(6))(C(12)H(8)N(2))(H(2)O]·H(2)O}(n), was obtained under solvothermal conditions. The Mn(2+) cation exhibits a distorted penta-gonal-bipyramidal MnN(2)O(5) coordination sphere with the water O atom and one of the phenanthroline N atoms in the axial positions. The cation is bridged by the doubly deprotonated 4,4'-[(4-carb--oxy-benz-yl)nitrilo]-dibenzoate ligand, generating a polymeric chain parallel to [100]. O-H⋯O hydrogen bonding, as well as π-π inter-actions between neighbouring phenanthroline ligands, with centroid-centroid distances of 3.695 (1) Å, lead to the construction of a three-dimensional network.

Related literature

For background to compounds with metal-organic-framework structures (MOFs), see: Corma et al. (2010 ▶); Feng et al. (2009 ▶); Lin et al. (2010 ▶); Ma et al. (2010 ▶); Sarma et al. (2011 ▶).

Experimental

Crystal data

[Mn(C22H15NO6)(C12H8N2)(H2O]·H2O

M = 660.53

Monoclinic,

a = 15.142 (2) Å

b = 9.6734 (13) Å

c = 21.313 (3) Å

β = 107.445 (3)°

V = 2978.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 273 K

0.32 × 0.27 × 0.23 mm

Data collection

Bruker APEX SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.851, T max = 0.891

14335 measured reflections

5235 independent reflections

3488 reflections with I > 2σ(I)

R int = 0.102

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.156

S = 0.95

5235 reflections

410 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016819/wm2618sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016819/wm2618Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016819/wm2618Isup3.cdx

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

[Mn(C22H15NO6)(C12H8N2)(H2O]·H2O	F(000) = 1364
Mr = 660.53	Dx = 1.473 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2883 reflections
a = 15.142 (2) Å	θ = 2.3–27.9°
b = 9.6734 (13) Å	µ = 0.50 mm−1
c = 21.313 (3) Å	T = 273 K
β = 107.445 (3)°	Block, colorless
V = 2978.4 (7) Å3	0.32 × 0.27 × 0.23 mm
Z = 4

Bruker APEX SMART CCD diffractometer	5235 independent reflections
Radiation source: fine-focus sealed tube	3488 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.102
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→17
Tmin = 0.851, Tmax = 0.891	k = −11→11
14335 measured reflections	l = −25→15

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0787P)2] where P = (Fo2 + 2Fc2)/3
5235 reflections	(Δ/σ)max = 0.001
410 parameters	Δρmax = 0.62 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
C1	0.3740 (2)	0.7528 (3)	0.29214 (19)	0.0385 (8)
C2	0.2736 (2)	0.7716 (3)	0.25997 (18)	0.0412 (8)
C3	0.2389 (3)	0.7855 (4)	0.1934 (2)	0.0543 (10)
H3	0.2792	0.7920	0.1681	0.065*
C4	0.1436 (3)	0.7902 (4)	0.1629 (2)	0.0606 (11)
H4	0.1210	0.7955	0.1173	0.073*
C5	0.0817 (2)	0.7869 (4)	0.2000 (2)	0.0528 (10)
C6	0.1170 (2)	0.7801 (4)	0.2663 (2)	0.0531 (10)
H6	0.0773	0.7823	0.2922	0.064*
C7	0.2110 (2)	0.7702 (3)	0.2959 (2)	0.0478 (9)
H7	0.2332	0.7622	0.3415	0.057*
C8	−0.0824 (3)	0.7829 (4)	0.2049 (2)	0.0564 (10)
C9	−0.1346 (3)	0.8984 (4)	0.2073 (2)	0.0589 (11)
H9	−0.1226	0.9813	0.1893	0.071*
C10	−0.2044 (3)	0.8919 (4)	0.2363 (2)	0.0524 (10)
H10	−0.2394	0.9702	0.2375	0.063*
C11	−0.2229 (2)	0.7697 (3)	0.26370 (17)	0.0415 (8)
C12	−0.3046 (3)	0.7581 (4)	0.28836 (19)	0.0469 (9)
C13	−0.1686 (2)	0.6567 (4)	0.2626 (2)	0.0511 (10)
H13	−0.1787	0.5747	0.2822	0.061*
C14	−0.0992 (3)	0.6628 (4)	0.2329 (2)	0.0609 (11)
H14	−0.0639	0.5847	0.2319	0.073*
C15	−0.0547 (3)	0.7657 (4)	0.1000 (2)	0.0675 (12)
H15A	−0.0172	0.8111	0.0764	0.081*
H15B	−0.1161	0.8062	0.0855	0.081*
C16	−0.0618 (3)	0.6100 (4)	0.0825 (2)	0.0592 (11)
C17	−0.1327 (3)	0.5656 (5)	0.0317 (3)	0.0939 (17)
H17	−0.1743	0.6293	0.0064	0.113*
C18	−0.1442 (3)	0.4278 (5)	0.0170 (3)	0.099 (2)
H18	−0.1964	0.3987	−0.0160	0.119*
C19	−0.0806 (3)	0.3322 (4)	0.0497 (2)	0.0566 (10)
C20	−0.0882 (3)	0.1837 (5)	0.0329 (2)	0.0652 (12)
C21	−0.0069 (3)	0.3772 (5)	0.0987 (2)	0.0753 (13)
H21	0.0383	0.3148	0.1211	0.090*
C22	0.0016 (3)	0.5167 (4)	0.1156 (2)	0.0707 (13)
H22	0.0517	0.5462	0.1502	0.085*
C23	0.5734 (3)	1.0407 (4)	0.3660 (2)	0.0578 (10)
H23	0.5594	1.0478	0.3205	0.069*
C24	0.5840 (3)	1.1605 (4)	0.4018 (3)	0.0762 (14)
H24	0.5780	1.2461	0.3810	0.091*
C25	0.6034 (4)	1.1522 (4)	0.4681 (3)	0.0815 (15)
H25	0.6106	1.2325	0.4931	0.098*
C26	0.6127 (3)	1.0233 (4)	0.4988 (2)	0.0615 (11)
C27	0.6320 (3)	1.0064 (5)	0.5675 (2)	0.0796 (14)
H27	0.6385	1.0839	0.5943	0.096*
C28	0.6411 (3)	0.8794 (5)	0.5946 (2)	0.0787 (14)
H28	0.6543	0.8709	0.6399	0.094*
C29	0.6310 (3)	0.7583 (4)	0.55564 (19)	0.0551 (10)
C30	0.6373 (3)	0.6263 (5)	0.5807 (2)	0.0684 (12)
H30	0.6486	0.6131	0.6256	0.082*
C31	0.6274 (4)	0.5170 (5)	0.5410 (2)	0.0806 (15)
H31	0.6317	0.4276	0.5577	0.097*
C32	0.6105 (3)	0.5400 (4)	0.4740 (2)	0.0673 (12)
H32	0.6062	0.4634	0.4469	0.081*
C33	0.6116 (2)	0.7712 (4)	0.48698 (16)	0.0406 (8)
C34	0.6021 (2)	0.9068 (3)	0.45838 (18)	0.0439 (9)
Mn1	0.55471 (3)	0.71229 (5)	0.33754 (2)	0.03684 (19)
N1	0.58186 (19)	0.9152 (3)	0.39227 (14)	0.0423 (7)
N2	0.60042 (19)	0.6619 (3)	0.44679 (14)	0.0415 (7)
N3	−0.0154 (2)	0.7910 (4)	0.16835 (18)	0.0635 (9)
O1	0.43035 (16)	0.7798 (2)	0.26018 (12)	0.0466 (6)
O2	0.40297 (16)	0.7085 (2)	0.34972 (13)	0.0504 (6)
O3	−0.37284 (18)	0.8342 (3)	0.26431 (14)	0.0684 (8)
O4	−0.30488 (16)	0.6694 (3)	0.33120 (14)	0.0535 (7)
O8	0.8366 (2)	0.9035 (3)	0.94467 (16)	0.0802 (9)*
H8A	0.7988	0.8752	0.9089	0.096*
H8B	0.8773	0.8417	0.9599	0.120*
O9	0.52533 (15)	0.4896 (2)	0.31171 (12)	0.0470 (6)
H9B	0.5622	0.4606	0.2914	0.056*
H9A	0.4717	0.4808	0.2883	0.070*
O11	−0.0275 (3)	0.1014 (3)	0.0524 (2)	0.1007 (13)
O12	−0.1701 (2)	0.1488 (3)	−0.00651 (18)	0.0895 (11)
H12	−0.1699	0.0666	−0.0158	0.134*

	U11	U22	U33	U12	U13	U23
C1	0.041 (2)	0.0294 (17)	0.047 (2)	−0.0021 (14)	0.0158 (18)	−0.0031 (16)
C2	0.041 (2)	0.0359 (19)	0.046 (2)	−0.0024 (15)	0.0128 (18)	−0.0018 (17)
C3	0.053 (2)	0.067 (3)	0.046 (2)	−0.002 (2)	0.018 (2)	−0.001 (2)
C4	0.057 (3)	0.078 (3)	0.040 (2)	0.001 (2)	0.003 (2)	0.001 (2)
C5	0.039 (2)	0.054 (2)	0.066 (3)	−0.0064 (18)	0.018 (2)	0.000 (2)
C6	0.043 (2)	0.059 (2)	0.060 (3)	−0.0049 (18)	0.019 (2)	0.003 (2)
C7	0.043 (2)	0.049 (2)	0.054 (2)	−0.0046 (17)	0.0185 (19)	0.0010 (18)
C8	0.059 (2)	0.056 (2)	0.067 (3)	0.003 (2)	0.040 (2)	0.000 (2)
C9	0.069 (3)	0.051 (2)	0.067 (3)	−0.001 (2)	0.035 (2)	0.009 (2)
C10	0.054 (2)	0.046 (2)	0.061 (3)	0.0094 (17)	0.023 (2)	−0.0004 (19)
C11	0.042 (2)	0.044 (2)	0.038 (2)	0.0005 (16)	0.0124 (17)	−0.0012 (17)
C12	0.045 (2)	0.054 (2)	0.042 (2)	0.0016 (17)	0.0130 (18)	−0.0084 (19)
C13	0.053 (2)	0.045 (2)	0.063 (3)	0.0002 (18)	0.029 (2)	0.0066 (19)
C14	0.067 (3)	0.047 (2)	0.084 (3)	0.0106 (19)	0.045 (2)	0.007 (2)
C15	0.059 (3)	0.080 (3)	0.063 (3)	−0.001 (2)	0.018 (2)	0.004 (2)
C16	0.063 (3)	0.064 (3)	0.057 (3)	0.003 (2)	0.027 (2)	0.000 (2)
C17	0.068 (3)	0.086 (4)	0.110 (5)	0.004 (3)	0.001 (3)	−0.013 (3)
C18	0.069 (3)	0.077 (4)	0.136 (6)	−0.002 (3)	0.007 (3)	−0.036 (3)
C19	0.060 (3)	0.061 (3)	0.055 (3)	−0.011 (2)	0.027 (2)	−0.009 (2)
C20	0.065 (3)	0.073 (3)	0.060 (3)	−0.011 (2)	0.022 (2)	−0.016 (2)
C21	0.082 (3)	0.072 (3)	0.064 (3)	−0.001 (2)	0.010 (3)	−0.007 (3)
C22	0.071 (3)	0.069 (3)	0.062 (3)	−0.016 (2)	0.004 (2)	−0.016 (2)
C23	0.075 (3)	0.047 (2)	0.054 (3)	−0.001 (2)	0.024 (2)	0.005 (2)
C24	0.112 (4)	0.037 (2)	0.081 (4)	−0.006 (2)	0.032 (3)	0.001 (2)
C25	0.125 (4)	0.043 (3)	0.073 (4)	−0.006 (3)	0.024 (3)	−0.015 (3)
C26	0.082 (3)	0.055 (3)	0.047 (3)	−0.006 (2)	0.018 (2)	−0.015 (2)
C27	0.110 (4)	0.074 (3)	0.049 (3)	−0.011 (3)	0.015 (3)	−0.027 (3)
C28	0.100 (4)	0.095 (4)	0.033 (2)	−0.006 (3)	0.008 (2)	−0.015 (3)
C29	0.063 (3)	0.065 (3)	0.036 (2)	−0.003 (2)	0.013 (2)	−0.003 (2)
C30	0.086 (3)	0.079 (3)	0.037 (2)	0.001 (3)	0.015 (2)	0.015 (2)
C31	0.125 (4)	0.061 (3)	0.051 (3)	0.001 (3)	0.019 (3)	0.020 (2)
C32	0.112 (4)	0.045 (2)	0.044 (3)	0.003 (2)	0.022 (2)	0.001 (2)
C33	0.042 (2)	0.050 (2)	0.0301 (19)	−0.0005 (16)	0.0098 (16)	−0.0036 (17)
C34	0.049 (2)	0.044 (2)	0.037 (2)	−0.0039 (16)	0.0098 (18)	−0.0060 (17)
Mn1	0.0429 (3)	0.0387 (3)	0.0309 (3)	0.0016 (2)	0.0141 (2)	−0.0008 (2)
N1	0.0543 (18)	0.0370 (16)	0.0385 (18)	−0.0025 (13)	0.0183 (15)	0.0005 (13)
N2	0.0516 (18)	0.0366 (16)	0.0367 (17)	0.0020 (13)	0.0141 (14)	0.0019 (14)
N3	0.054 (2)	0.083 (3)	0.060 (2)	−0.0020 (18)	0.0272 (18)	0.0002 (19)
O1	0.0400 (14)	0.0557 (15)	0.0485 (15)	0.0001 (11)	0.0202 (12)	0.0087 (12)
O2	0.0480 (15)	0.0593 (16)	0.0463 (17)	0.0040 (12)	0.0176 (13)	0.0083 (13)
O3	0.0496 (17)	0.101 (2)	0.0576 (19)	0.0240 (15)	0.0211 (14)	0.0105 (17)
O4	0.0480 (15)	0.0631 (16)	0.0564 (17)	0.0011 (12)	0.0260 (13)	0.0070 (14)
O9	0.0466 (14)	0.0496 (14)	0.0474 (15)	−0.0012 (11)	0.0180 (12)	−0.0133 (12)
O11	0.094 (3)	0.069 (2)	0.120 (3)	0.0039 (19)	0.002 (2)	−0.022 (2)
O12	0.081 (2)	0.076 (2)	0.105 (3)	−0.0160 (17)	0.018 (2)	−0.027 (2)

C1—O2	1.249 (4)	C21—C22	1.394 (5)
C1—O1	1.268 (4)	C21—H21	0.9300
C1—C2	1.480 (5)	C22—H22	0.9300
C2—C3	1.363 (5)	C23—N1	1.327 (4)
C2—C7	1.387 (5)	C23—C24	1.370 (6)
C3—C4	1.395 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.357 (6)
C4—C5	1.397 (6)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.396 (6)
C5—C6	1.354 (6)	C25—H25	0.9300
C5—N3	1.423 (5)	C26—C34	1.398 (5)
C6—C7	1.376 (5)	C26—C27	1.413 (6)
C6—H6	0.9300	C27—C28	1.347 (6)
C7—H7	0.9300	C27—H27	0.9300
C8—C14	1.364 (5)	C28—C29	1.417 (6)
C8—C9	1.380 (5)	C28—H28	0.9300
C8—N3	1.454 (5)	C29—C30	1.377 (6)
C9—C10	1.376 (5)	C29—C33	1.409 (5)
C9—H9	0.9300	C30—C31	1.334 (6)
C10—C11	1.384 (5)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.390 (6)
C11—C13	1.372 (5)	C31—H31	0.9300
C11—C12	1.486 (5)	C32—N2	1.302 (4)
C12—O3	1.247 (4)	C32—H32	0.9300
C12—O4	1.254 (4)	C33—N2	1.340 (4)
C13—C14	1.381 (5)	C33—C34	1.436 (5)
C13—H13	0.9300	C34—N1	1.352 (4)
C14—H14	0.9300	Mn1—O1	2.198 (2)
C15—N3	1.420 (5)	Mn1—O4i	2.210 (2)
C15—C16	1.548 (6)	Mn1—O9	2.235 (2)
C15—H15A	0.9700	Mn1—N1	2.258 (3)
C15—H15B	0.9700	Mn1—N2	2.274 (3)
C16—C17	1.346 (6)	Mn1—O2	2.389 (2)
C16—C22	1.352 (5)	Mn1—O3i	2.461 (3)
C17—C18	1.368 (6)	O3—Mn1ii	2.461 (3)
C17—H17	0.9300	O4—Mn1ii	2.210 (2)
C18—C19	1.367 (6)	O8—H8A	0.8501
C18—H18	0.9300	O8—H8B	0.8500
C19—C21	1.351 (5)	O9—H9B	0.8501
C19—C20	1.477 (6)	O9—H9A	0.8200
C20—O11	1.193 (5)	O12—H12	0.8199
C20—O12	1.316 (5)
O2—C1—O1	120.3 (3)	C25—C24—C23	118.8 (4)
O2—C1—C2	120.4 (3)	C25—C24—H24	120.6
O1—C1—C2	119.2 (3)	C23—C24—H24	120.6
C3—C2—C7	117.5 (3)	C24—C25—C26	120.1 (4)
C3—C2—C1	121.1 (4)	C24—C25—H25	119.9
C7—C2—C1	121.4 (3)	C26—C25—H25	119.9
C2—C3—C4	120.7 (4)	C25—C26—C34	117.0 (4)
C2—C3—H3	119.6	C25—C26—C27	123.3 (4)
C4—C3—H3	119.6	C34—C26—C27	119.7 (4)
C3—C4—C5	120.7 (4)	C28—C27—C26	120.8 (4)
C3—C4—H4	119.6	C28—C27—H27	119.6
C5—C4—H4	119.6	C26—C27—H27	119.6
C6—C5—C4	118.1 (3)	C27—C28—C29	121.6 (4)
C6—C5—N3	121.7 (4)	C27—C28—H28	119.2
C4—C5—N3	120.2 (4)	C29—C28—H28	119.2
C5—C6—C7	120.8 (4)	C30—C29—C33	117.0 (4)
C5—C6—H6	119.6	C30—C29—C28	123.8 (4)
C7—C6—H6	119.6	C33—C29—C28	119.2 (4)
C6—C7—C2	122.0 (4)	C31—C30—C29	120.5 (4)
C6—C7—H7	119.0	C31—C30—H30	119.7
C2—C7—H7	119.0	C29—C30—H30	119.7
C14—C8—C9	119.2 (4)	C30—C31—C32	118.4 (4)
C14—C8—N3	122.2 (4)	C30—C31—H31	120.8
C9—C8—N3	118.4 (4)	C32—C31—H31	120.8
C10—C9—C8	120.4 (4)	N2—C32—C31	124.3 (4)
C10—C9—H9	119.8	N2—C32—H32	117.9
C8—C9—H9	119.8	C31—C32—H32	117.9
C9—C10—C11	120.6 (3)	N2—C33—C29	122.8 (3)
C9—C10—H10	119.7	N2—C33—C34	118.2 (3)
C11—C10—H10	119.7	C29—C33—C34	119.0 (3)
C13—C11—C10	118.3 (3)	N1—C34—C26	122.9 (3)
C13—C11—C12	120.8 (3)	N1—C34—C33	117.4 (3)
C10—C11—C12	120.6 (3)	C26—C34—C33	119.7 (3)
O3—C12—O4	121.3 (4)	O1—Mn1—O4i	129.32 (10)
O3—C12—C11	119.0 (4)	O1—Mn1—O9	92.24 (9)
O4—C12—C11	119.6 (3)	O4i—Mn1—O9	85.88 (9)
C11—C13—C14	121.1 (3)	O1—Mn1—N1	96.41 (10)
C11—C13—H13	119.5	O4i—Mn1—N1	99.52 (10)
C14—C13—H13	119.5	O9—Mn1—N1	163.23 (10)
C8—C14—C13	120.3 (4)	O1—Mn1—N2	139.57 (10)
C8—C14—H14	119.8	O4i—Mn1—N2	91.11 (10)
C13—C14—H14	119.8	O9—Mn1—N2	91.28 (9)
N3—C15—C16	113.1 (4)	N1—Mn1—N2	72.85 (10)
N3—C15—H15A	109.0	O1—Mn1—O2	56.65 (9)
C16—C15—H15A	109.0	O4i—Mn1—O2	168.03 (9)
N3—C15—H15B	109.0	O9—Mn1—O2	83.40 (8)
C16—C15—H15B	109.0	N1—Mn1—O2	89.38 (9)
H15A—C15—H15B	107.8	N2—Mn1—O2	83.85 (9)
C17—C16—C22	118.5 (4)	O1—Mn1—O3i	80.00 (9)
C17—C16—C15	119.0 (4)	O4i—Mn1—O3i	55.33 (9)
C22—C16—C15	122.4 (4)	O9—Mn1—O3i	113.53 (10)
C16—C17—C18	120.8 (5)	N1—Mn1—O3i	82.21 (10)
C16—C17—H17	119.6	N2—Mn1—O3i	134.06 (10)
C18—C17—H17	119.6	O2—Mn1—O3i	134.63 (9)
C19—C18—C17	121.4 (5)	C23—N1—C34	117.3 (3)
C19—C18—H18	119.3	C23—N1—Mn1	126.7 (3)
C17—C18—H18	119.3	C34—N1—Mn1	115.8 (2)
C21—C19—C18	117.9 (4)	C32—N2—C33	117.0 (3)
C21—C19—C20	119.2 (4)	C32—N2—Mn1	127.5 (3)
C18—C19—C20	122.9 (4)	C33—N2—Mn1	115.3 (2)
O11—C20—O12	122.1 (4)	C15—N3—C5	122.5 (4)
O11—C20—C19	124.7 (4)	C15—N3—C8	113.3 (3)
O12—C20—C19	113.2 (4)	C5—N3—C8	122.1 (4)
C19—C21—C22	120.2 (4)	C1—O1—Mn1	95.7 (2)
C19—C21—H21	119.9	C1—O2—Mn1	87.3 (2)
C22—C21—H21	119.9	C12—O3—Mn1ii	85.9 (2)
C16—C22—C21	121.0 (4)	C12—O4—Mn1ii	97.4 (2)
C16—C22—H22	119.5	H8A—O8—H8B	109.5
C21—C22—H22	119.5	Mn1—O9—H9B	109.3
N1—C23—C24	123.9 (4)	Mn1—O9—H9A	109.8
N1—C23—H23	118.0	H9B—O9—H9A	109.8
C24—C23—H23	118.0	C20—O12—H12	109.4

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O4iii	0.85	1.96	2.798 (4)	170
O8—H8B···O11iv	0.85	2.43	2.872 (5)	113
O9—H9B···O1v	0.85	2.09	2.745 (3)	134
O9—H9A···O3vi	0.82	2.12	2.824 (3)	144
O12—H12···O8vii	0.82	1.81	2.605 (4)	165

Table 1

Selected bond lengths (Å)

Mn1—O1	2.198 (2)
Mn1—O4i	2.210 (2)
Mn1—O9	2.235 (2)
Mn1—N1	2.258 (3)
Mn1—N2	2.274 (3)
Mn1—O2	2.389 (2)
Mn1—O3i	2.461 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O4ii	0.85	1.96	2.798 (4)	170
O8—H8B⋯O11iii	0.85	2.43	2.872 (5)	113
O9—H9B⋯O1iv	0.85	2.09	2.745 (3)	134
O9—H9A⋯O3v	0.82	2.12	2.824 (3)	144
O12—H12⋯O8vi	0.82	1.81	2.605 (4)	165

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