Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ato)manganese(II)]-μ(3)-4,4'-oxydibenzoato] monohydrate].

In the title compound, {[Mn(C(16)H(18)N(3)O(3))(C(14)H(8)O(5))]·H(2)O}(n), the unique Mn(II) ion is coordinated by two O atoms from a chelating 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ate ligand and three O atoms from three 4,4'-oxydibenzoate ligands, forming a distorted square-pyramidal coordination environment. In the crystal structure, centrosymmetric dinuclear manganese units are linked via 4,4'-oxydibenzoate ligands into one-dimensional chains; these chains are, in turn, connected via inter-molecular N-H⋯O and O-H⋯O hydrogen bonds to form a two-dimensional supra-molecular network. The O atom of the solvent water mol-ecule is disordered over two sites with equal occupancies; the attached H atoms are common to both sites.

Related literature

For general background, see: Xiao et al. (2005 ▶). For a related structure, see: An et al. (2007 ▶).

Experimental

Crystal data

[Mn(C16H18N3O3)(C14H8O5)]·H2O

M = 648.49

Triclinic,

a = 10.208 (5) Å

b = 11.915 (5) Å

c = 13.202 (5) Å

α = 100.751 (5)°

β = 112.010 (5)°

γ = 102.318 (5)°

V = 1390.1 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.55 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.908

13533 measured reflections

6236 independent reflections

5434 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.129

S = 1.05

6236 reflections

407 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807060825/lh2564sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060825/lh2564Isup2.hkl

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

[Mn(C16H18N3O3)(C14H8O5)]·H2O	Z = 2
Mr = 648.49	F000 = 670
Triclinic, P1	Dx = 1.549 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.208 (5) Å	Cell parameters from 13533 reflections
b = 11.915 (5) Å	θ = 3.2–27.5º
c = 13.202 (5) Å	µ = 0.55 mm−1
α = 100.751 (5)º	T = 298 (2) K
β = 112.010 (5)º	Block, colorless
γ = 102.318 (5)º	0.23 × 0.20 × 0.18 mm
V = 1390.1 (10) Å3

Bruker SMART APEX CCD area-detector diffractometer	6236 independent reflections
Radiation source: fine-focus sealed tube	5434 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 298(2) K	θmax = 27.5º
ω scans	θmin = 3.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.885, Tmax = 0.908	k = −14→15
13533 measured reflections	l = −17→17

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0863P)2 + 0.3678P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
6236 reflections	Δρmax = 0.55 e Å−3
407 parameters	Δρmin = −0.35 e Å−3
6 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	0.87296 (3)	0.44003 (2)	0.32348 (2)	0.02128 (10)
C1	1.1128 (2)	0.82195 (16)	0.49788 (16)	0.0247 (4)
C2	1.1270 (2)	0.90958 (17)	0.59100 (16)	0.0264 (4)
H2A	1.0997	0.8865	0.6456	0.032*
C3	1.1812 (2)	1.03007 (17)	0.60306 (16)	0.0273 (4)
H3A	1.1903	1.0879	0.6654	0.033*
C4	1.2219 (2)	1.06439 (16)	0.52159 (17)	0.0262 (4)
C5	1.2094 (2)	0.97946 (18)	0.42831 (18)	0.0314 (4)
H5A	1.2378	1.0029	0.3743	0.038*
C6	1.1536 (2)	0.85872 (17)	0.41711 (18)	0.0297 (4)
H6A	1.1432	0.8010	0.3541	0.036*
C7	1.0531 (2)	0.69147 (17)	0.48503 (18)	0.0264 (4)
C8	1.4875 (2)	1.36779 (17)	0.38123 (17)	0.0265 (4)
C9	1.3520 (2)	1.37948 (19)	0.37526 (19)	0.0323 (4)
H9A	1.3122	1.4316	0.3380	0.039*
C10	1.2758 (2)	1.31470 (19)	0.42401 (19)	0.0315 (4)
H10A	1.1860	1.3237	0.4205	0.038*
C11	1.3354 (2)	1.23664 (16)	0.47793 (17)	0.0280 (4)
C12	1.4669 (2)	1.21939 (18)	0.48114 (18)	0.0329 (4)
H12A	1.5031	1.1635	0.5143	0.039*
C13	1.5432 (2)	1.28651 (19)	0.43436 (18)	0.0303 (4)
H13A	1.6331	1.2773	0.4384	0.036*
C14	1.5780 (2)	1.44426 (18)	0.33786 (18)	0.0298 (4)
C15	0.72279 (18)	0.18861 (15)	0.16263 (14)	0.0198 (3)
C16	0.84417 (19)	0.18967 (15)	0.13214 (15)	0.0208 (3)
C17	0.8599 (2)	0.08327 (16)	0.08805 (16)	0.0247 (4)
H17A	0.9375	0.0866	0.0669	0.030*
C18	0.65597 (18)	−0.03553 (15)	0.10430 (14)	0.0201 (3)
C19	0.62933 (18)	0.06987 (15)	0.14683 (14)	0.0195 (3)
C20	0.51069 (19)	0.06089 (16)	0.17796 (15)	0.0224 (3)
H20A	0.4918	0.1299	0.2068	0.027*
C21	0.42376 (19)	−0.04923 (17)	0.16565 (16)	0.0239 (4)
C22	0.44917 (19)	−0.15747 (15)	0.12569 (15)	0.0216 (3)
C23	0.56632 (19)	−0.14844 (15)	0.09490 (15)	0.0208 (3)
H23A	0.5859	−0.2178	0.0677	0.025*
C24	0.3535 (2)	−0.28055 (17)	0.22389 (17)	0.0278 (4)
H24A	0.3440	−0.2084	0.2647	0.033*
H24B	0.4467	−0.2906	0.2713	0.033*
C25	0.2255 (2)	−0.38815 (17)	0.20169 (19)	0.0303 (4)
H25A	0.2272	−0.3970	0.2737	0.036*
H25B	0.1318	−0.3765	0.1578	0.036*
C26	0.2411 (2)	−0.48454 (17)	0.02785 (17)	0.0314 (4)
H26A	0.1473	−0.4761	−0.0203	0.038*
H26B	0.2525	−0.5562	−0.0121	0.038*
C27	0.3680 (2)	−0.37514 (16)	0.04987 (16)	0.0271 (4)
H27A	0.4625	−0.3864	0.0925	0.032*
H27B	0.3646	−0.3653	−0.0223	0.032*
C28	0.95504 (19)	0.30350 (15)	0.14442 (16)	0.0230 (4)
C29	0.8106 (2)	−0.13254 (17)	0.02814 (19)	0.0298 (4)
H29A	0.8568	−0.1147	−0.0216	0.036*
H29B	0.7203	−0.1998	−0.0167	0.036*
C30	0.9141 (3)	−0.1668 (2)	0.1229 (2)	0.0460 (6)
H30A	0.9362	−0.2358	0.0915	0.069*
H30B	0.8681	−0.1855	0.1718	0.069*
H30C	1.0044	−0.1010	0.1665	0.069*
F1	0.30490 (14)	−0.05557 (11)	0.18978 (12)	0.0368 (3)
N1	0.77241 (17)	−0.02611 (13)	0.07263 (14)	0.0234 (3)
N2	0.35453 (17)	−0.26761 (13)	0.11516 (13)	0.0232 (3)
N3	0.23945 (18)	−0.49768 (14)	0.13743 (14)	0.0272 (3)
H3B	0.1626	−0.5617	0.1228	0.033*
H3C	0.3240	−0.5105	0.1802	0.033*
O1	1.01455 (17)	0.61842 (12)	0.38860 (14)	0.0356 (3)
O2	1.04421 (16)	0.66314 (13)	0.56977 (14)	0.0323 (3)
O3	1.71509 (15)	1.46076 (13)	0.38222 (13)	0.0342 (3)
O4	1.51348 (18)	1.48909 (17)	0.26125 (17)	0.0451 (4)
O5	1.26452 (19)	1.18672 (13)	0.53831 (14)	0.0360 (3)
O6	0.69325 (14)	0.28045 (11)	0.19922 (12)	0.0260 (3)
O7	0.96748 (15)	0.40179 (12)	0.20826 (12)	0.0291 (3)
O8	1.03114 (17)	0.29361 (12)	0.08966 (14)	0.0366 (4)
O1W	0.7413 (5)	0.5678 (6)	0.2066 (4)	0.0338 (16)	0.50 (2)
H1	0.8224	0.6189	0.2575	0.051*
H2	0.6698	0.5411	0.2226	0.051*
O1W'	0.7286 (5)	0.6219 (15)	0.2009 (4)	0.064 (3)	0.50 (2)

	U11	U22	U33	U12	U13	U23
Mn1	0.02024 (16)	0.01816 (15)	0.02471 (16)	0.00072 (10)	0.01335 (11)	0.00295 (11)
C1	0.0233 (9)	0.0223 (9)	0.0277 (9)	0.0064 (7)	0.0100 (7)	0.0088 (7)
C2	0.0276 (9)	0.0303 (10)	0.0235 (9)	0.0084 (7)	0.0120 (7)	0.0111 (7)
C3	0.0333 (10)	0.0251 (9)	0.0217 (9)	0.0085 (7)	0.0113 (7)	0.0047 (7)
C4	0.0290 (10)	0.0202 (8)	0.0281 (9)	0.0054 (7)	0.0120 (7)	0.0074 (7)
C5	0.0406 (11)	0.0261 (9)	0.0300 (10)	0.0049 (8)	0.0209 (8)	0.0080 (8)
C6	0.0356 (11)	0.0235 (9)	0.0302 (10)	0.0053 (7)	0.0184 (8)	0.0039 (7)
C7	0.0199 (9)	0.0237 (9)	0.0373 (10)	0.0071 (7)	0.0136 (7)	0.0098 (8)
C8	0.0223 (9)	0.0252 (9)	0.0318 (10)	0.0059 (7)	0.0130 (7)	0.0071 (7)
C9	0.0314 (11)	0.0360 (11)	0.0426 (12)	0.0168 (8)	0.0214 (9)	0.0214 (9)
C10	0.0287 (10)	0.0331 (10)	0.0395 (11)	0.0105 (8)	0.0193 (8)	0.0149 (9)
C11	0.0343 (10)	0.0203 (8)	0.0271 (9)	0.0026 (7)	0.0152 (8)	0.0047 (7)
C12	0.0404 (11)	0.0278 (10)	0.0330 (10)	0.0144 (8)	0.0149 (9)	0.0122 (8)
C13	0.0237 (9)	0.0321 (10)	0.0357 (11)	0.0115 (7)	0.0123 (8)	0.0096 (8)
C14	0.0269 (10)	0.0271 (9)	0.0386 (11)	0.0086 (7)	0.0189 (8)	0.0070 (8)
C15	0.0185 (8)	0.0178 (8)	0.0187 (8)	0.0002 (6)	0.0073 (6)	0.0038 (6)
C16	0.0178 (8)	0.0193 (8)	0.0235 (8)	−0.0016 (6)	0.0115 (6)	0.0050 (6)
C17	0.0220 (9)	0.0221 (8)	0.0302 (9)	0.0002 (6)	0.0164 (7)	0.0048 (7)
C18	0.0184 (8)	0.0195 (8)	0.0205 (8)	0.0010 (6)	0.0092 (6)	0.0052 (6)
C19	0.0185 (8)	0.0190 (8)	0.0188 (8)	0.0012 (6)	0.0086 (6)	0.0050 (6)
C20	0.0212 (9)	0.0207 (8)	0.0248 (8)	0.0026 (6)	0.0128 (7)	0.0041 (7)
C21	0.0171 (8)	0.0268 (9)	0.0292 (9)	0.0013 (6)	0.0150 (7)	0.0072 (7)
C22	0.0208 (8)	0.0192 (8)	0.0206 (8)	−0.0018 (6)	0.0085 (6)	0.0067 (6)
C23	0.0186 (8)	0.0170 (8)	0.0247 (8)	0.0009 (6)	0.0103 (6)	0.0048 (6)
C24	0.0331 (10)	0.0230 (9)	0.0271 (9)	0.0009 (7)	0.0165 (8)	0.0084 (7)
C25	0.0330 (11)	0.0257 (9)	0.0395 (11)	0.0051 (8)	0.0238 (9)	0.0133 (8)
C26	0.0347 (11)	0.0220 (9)	0.0281 (10)	−0.0059 (7)	0.0127 (8)	0.0050 (7)
C27	0.0311 (10)	0.0205 (8)	0.0254 (9)	−0.0025 (7)	0.0143 (7)	0.0051 (7)
C28	0.0219 (9)	0.0187 (8)	0.0270 (9)	−0.0015 (6)	0.0141 (7)	0.0052 (7)
C29	0.0315 (10)	0.0193 (8)	0.0406 (11)	0.0031 (7)	0.0237 (8)	0.0011 (7)
C30	0.0532 (15)	0.0436 (13)	0.0495 (14)	0.0252 (11)	0.0262 (12)	0.0118 (11)
F1	0.0323 (7)	0.0301 (6)	0.0591 (8)	0.0045 (5)	0.0345 (6)	0.0122 (6)
N1	0.0222 (7)	0.0173 (7)	0.0319 (8)	0.0020 (5)	0.0167 (6)	0.0039 (6)
N2	0.0238 (8)	0.0188 (7)	0.0248 (8)	−0.0020 (5)	0.0126 (6)	0.0070 (6)
N3	0.0251 (8)	0.0222 (7)	0.0341 (9)	0.0002 (6)	0.0152 (7)	0.0111 (6)
O1	0.0395 (8)	0.0201 (6)	0.0445 (9)	0.0001 (6)	0.0227 (7)	0.0043 (6)
O2	0.0312 (7)	0.0333 (7)	0.0440 (8)	0.0142 (6)	0.0213 (6)	0.0214 (6)
O3	0.0235 (7)	0.0362 (8)	0.0410 (8)	0.0066 (6)	0.0180 (6)	0.0017 (6)
O4	0.0338 (9)	0.0575 (10)	0.0628 (11)	0.0180 (7)	0.0291 (8)	0.0375 (9)
O5	0.0542 (10)	0.0213 (7)	0.0401 (8)	0.0064 (6)	0.0314 (7)	0.0087 (6)
O6	0.0214 (6)	0.0181 (6)	0.0350 (7)	0.0007 (5)	0.0144 (5)	0.0017 (5)
O7	0.0322 (7)	0.0191 (6)	0.0358 (8)	−0.0029 (5)	0.0232 (6)	0.0017 (5)
O8	0.0412 (9)	0.0226 (7)	0.0504 (9)	−0.0047 (6)	0.0370 (7)	0.0003 (6)
O1W	0.0325 (17)	0.036 (2)	0.0339 (17)	0.0081 (9)	0.0168 (11)	0.0111 (9)
O1W'	0.051 (3)	0.092 (8)	0.057 (3)	0.018 (3)	0.028 (2)	0.035 (3)

Mn1—O3i	2.0723 (16)	C18—C19	1.401 (2)
Mn1—O2ii	2.0997 (15)	C18—C23	1.411 (2)
Mn1—O1	2.1028 (16)	C19—C20	1.408 (2)
Mn1—O7	2.1170 (15)	C20—C21	1.360 (2)
Mn1—O6	2.1827 (14)	C20—H20A	0.9300
C1—C6	1.390 (3)	C21—F1	1.356 (2)
C1—C2	1.395 (3)	C21—C22	1.414 (3)
C1—C7	1.496 (3)	C22—C23	1.390 (3)
C2—C3	1.379 (3)	C22—N2	1.402 (2)
C2—H2A	0.9300	C23—H23A	0.9300
C3—C4	1.387 (3)	C24—N2	1.476 (2)
C3—H3A	0.9300	C24—C25	1.515 (3)
C4—O5	1.378 (2)	C24—H24A	0.9700
C4—C5	1.385 (3)	C24—H24B	0.9700
C5—C6	1.387 (3)	C25—N3	1.483 (3)
C5—H5A	0.9300	C25—H25A	0.9700
C6—H6A	0.9300	C25—H25B	0.9700
C7—O2	1.256 (3)	C26—N3	1.490 (3)
C7—O1	1.264 (3)	C26—C27	1.523 (2)
C8—C9	1.393 (3)	C26—H26A	0.9700
C8—C13	1.394 (3)	C26—H26B	0.9700
C8—C14	1.498 (3)	C27—N2	1.468 (2)
C9—C10	1.386 (3)	C27—H27A	0.9700
C9—H9A	0.9300	C27—H27B	0.9700
C10—C11	1.380 (3)	C28—O8	1.252 (2)
C10—H10A	0.9300	C28—O7	1.259 (2)
C11—C12	1.387 (3)	C29—N1	1.487 (2)
C11—O5	1.392 (2)	C29—C30	1.494 (3)
C12—C13	1.381 (3)	C29—H29A	0.9700
C12—H12A	0.9300	C29—H29B	0.9700
C13—H13A	0.9300	C30—H30A	0.9600
C14—O3	1.251 (3)	C30—H30B	0.9600
C14—O4	1.263 (3)	C30—H30C	0.9600
C15—O6	1.255 (2)	N3—H3B	0.9000
C15—C16	1.437 (2)	N3—H3C	0.9000
C15—C19	1.456 (2)	O2—Mn1ii	2.0997 (15)
C16—C17	1.361 (3)	O3—Mn1iii	2.0723 (16)
C16—C28	1.507 (2)	O1W—H1	0.8501
C17—N1	1.344 (2)	O1W—H2	0.8500
C17—H17A	0.9300	O1W'—H1	0.9823
C18—N1	1.390 (2)	O1W'—H2	1.1648
O3i—Mn1—O2ii	94.25 (7)	C19—C20—H20A	120.1
O3i—Mn1—O1	99.66 (7)	F1—C21—C20	118.42 (16)
O2ii—Mn1—O1	110.98 (7)	F1—C21—C22	118.55 (15)
O3i—Mn1—O7	159.82 (6)	C20—C21—C22	123.01 (16)
O2ii—Mn1—O7	98.92 (6)	C23—C22—N2	123.11 (16)
O1—Mn1—O7	89.87 (6)	C23—C22—C21	117.17 (15)
O3i—Mn1—O6	83.01 (6)	N2—C22—C21	119.69 (16)
O2ii—Mn1—O6	90.64 (6)	C22—C23—C18	120.92 (16)
O1—Mn1—O6	157.82 (6)	C22—C23—H23A	119.5
O7—Mn1—O6	81.62 (6)	C18—C23—H23A	119.5
C6—C1—C2	118.53 (18)	N2—C24—C25	110.46 (16)
C6—C1—C7	121.02 (17)	N2—C24—H24A	109.6
C2—C1—C7	120.45 (18)	C25—C24—H24A	109.6
C3—C2—C1	120.77 (18)	N2—C24—H24B	109.6
C3—C2—H2A	119.6	C25—C24—H24B	109.6
C1—C2—H2A	119.6	H24A—C24—H24B	108.1
C2—C3—C4	119.57 (18)	N3—C25—C24	109.14 (16)
C2—C3—H3A	120.2	N3—C25—H25A	109.9
C4—C3—H3A	120.2	C24—C25—H25A	109.9
O5—C4—C5	124.49 (18)	N3—C25—H25B	109.9
O5—C4—C3	114.36 (17)	C24—C25—H25B	109.9
C5—C4—C3	121.01 (18)	H25A—C25—H25B	108.3
C4—C5—C6	118.62 (19)	N3—C26—C27	110.69 (15)
C4—C5—H5A	120.7	N3—C26—H26A	109.5
C6—C5—H5A	120.7	C27—C26—H26A	109.5
C5—C6—C1	121.51 (18)	N3—C26—H26B	109.5
C5—C6—H6A	119.2	C27—C26—H26B	109.5
C1—C6—H6A	119.2	H26A—C26—H26B	108.1
O2—C7—O1	125.27 (18)	N2—C27—C26	109.42 (16)
O2—C7—C1	117.92 (18)	N2—C27—H27A	109.8
O1—C7—C1	116.81 (18)	C26—C27—H27A	109.8
C9—C8—C13	118.67 (19)	N2—C27—H27B	109.8
C9—C8—C14	121.97 (18)	C26—C27—H27B	109.8
C13—C8—C14	119.29 (17)	H27A—C27—H27B	108.2
C10—C9—C8	121.04 (19)	O8—C28—O7	123.65 (15)
C10—C9—H9A	119.5	O8—C28—C16	116.83 (16)
C8—C9—H9A	119.5	O7—C28—C16	119.52 (16)
C11—C10—C9	118.86 (19)	N1—C29—C30	111.51 (17)
C11—C10—H10A	120.6	N1—C29—H29A	109.3
C9—C10—H10A	120.6	C30—C29—H29A	109.3
C10—C11—C12	121.40 (19)	N1—C29—H29B	109.3
C10—C11—O5	116.02 (19)	C30—C29—H29B	109.3
C12—C11—O5	122.25 (19)	H29A—C29—H29B	108.0
C13—C12—C11	119.01 (19)	C29—C30—H30A	109.5
C13—C12—H12A	120.5	C29—C30—H30B	109.5
C11—C12—H12A	120.5	H30A—C30—H30B	109.5
C12—C13—C8	120.93 (19)	C29—C30—H30C	109.5
C12—C13—H13A	119.5	H30A—C30—H30C	109.5
C8—C13—H13A	119.5	H30B—C30—H30C	109.5
O3—C14—O4	124.1 (2)	C17—N1—C18	119.41 (15)
O3—C14—C8	116.81 (19)	C17—N1—C29	117.84 (15)
O4—C14—C8	119.05 (18)	C18—N1—C29	122.66 (15)
O6—C15—C16	124.88 (15)	C22—N2—C27	115.72 (15)
O6—C15—C19	119.88 (16)	C22—N2—C24	114.10 (14)
C16—C15—C19	115.23 (15)	C27—N2—C24	111.64 (15)
C17—C16—C15	119.13 (15)	C25—N3—C26	110.69 (15)
C17—C16—C28	117.57 (16)	C25—N3—H3B	109.5
C15—C16—C28	123.30 (16)	C26—N3—H3B	109.5
N1—C17—C16	125.34 (17)	C25—N3—H3C	109.5
N1—C17—H17A	117.3	C26—N3—H3C	109.5
C16—C17—H17A	117.3	H3B—N3—H3C	108.1
N1—C18—C19	118.70 (15)	C7—O1—Mn1	127.16 (13)
N1—C18—C23	121.14 (16)	C7—O2—Mn1ii	139.01 (13)
C19—C18—C23	120.16 (16)	C14—O3—Mn1iii	136.07 (15)
C18—C19—C20	118.98 (16)	C4—O5—C11	120.98 (16)
C18—C19—C15	122.11 (16)	C15—O6—Mn1	119.80 (11)
C20—C19—C15	118.89 (16)	C28—O7—Mn1	131.03 (11)
C21—C20—C19	119.72 (17)	H1—O1W—H2	120.8
C21—C20—H20A	120.1	H1—O1W'—H2	86.6

D—H···A	D—H	H···A	D···A	D—H···A
O1W'—H2···O3i	1.16	2.40	3.359 (14)	138
O1W'—H2···O4i	1.16	1.87	2.874 (12)	142
N3—H3B···O8i	0.90	1.80	2.694 (3)	169
N3—H3C···O4iv	0.90	1.83	2.716 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W′—H2⋯O3i	1.16	2.40	3.359 (14)	138
O1W′—H2⋯O4i	1.16	1.87	2.874 (12)	142
N3—H3B⋯O8i	0.90	1.80	2.694 (3)	169
N3—H3C⋯O4ii	0.90	1.83	2.716 (3)	169

Symmetry codes: (i) ; (ii) .