Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato)manganese(II)]-μ3-4,4′-oxydibenzoato] monohydrate]

Hong, J.

doi:10.1107/S1600536807060825

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m21

https://doi.org/10.1107/S1600536807060825

Open

access

Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato)manganese(II)]-μ₃-4,4′-oxydibenzoato] monohydrate]

Jun Hong ^a ^*

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: junhong000@hotmail.com

(Received 8 November 2007; accepted 19 November 2007; online 6 December 2007)

In the title compound, {[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O}_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-dihydroquinoline-3-carboxylate 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 intermolecular N—H⋯O and O—H⋯O hydrogen bonds to form a two-dimensional supramolecular network. The O atom of the solvent water molecule 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_r = 648.49
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.129
S = 1.05
6236 reflections
407 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) x-1, y-1, z; (ii) x-1, y-2, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060825/lh2564Isup2.hkl

checkCIF report

Comment top

Norfloxacin [1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid, Hcf] is a member of a class of quinolones that is used to treat infections (Xiao et al. 2005; An et al. 2007). As a part of our ongoing investigations in this field, we report here the crystal structure of the title compound. In the crystal structure of the title compound, the Mn atoms are coordinated by three oxygen atoms of one Hcf ligand, one 4,4'-oxydibenzoate ligand and one oxygen atom from one symmetry related 4,4'-oxydibenzoate within a distorted square-pyramidal geometry (Figure 1). In the crystal structure, dinuclear manganese units are linked via the 4,4'-oxydibenzoate anions into a one-dimensional chain running along [-2, -3, 2]. Finally, one-dimensional chains are connected with N—H···O and O—H···O hydrogen bonds to form a two-dimensional supramolecular network.

Related literature top

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

Experimental top

The title compound was prepared by a hydrothermal method. A mixture of MnCl₂ (0.07 g 0.5 mmol), norfloxacin (0.16 g 0.5 mmol), 4,4'-oxy-bisbenzoic acid (0.13 g 0.5 mmol) and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 h under autogenous pressure. Single crystals of were obtained after cooling to room temperature.

Structure description top

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

Computing details top

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.

Figures top

Fig. 1. Part of the crystal structure with labeling and displacement ellipsoids drawn at the 50% probability level. [Symmetry code: i = x - 1,y - 1,z; ii = -x + 2,-y + 1,-z + 1]. The disorder is not showm.

catena-Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline- 3-carboxylato-κ²O³,O⁴)manganese(II)]-µ-4,4'-oxydibenzoato- κ³O,O':O''] monohydrate] top

Crystal data top

[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O	Z = 2
M_r = 648.49	F(000) = 670
Triclinic, P1	D_x = 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 = 3.2–27.5°
c = 13.202 (5) Å	µ = 0.55 mm⁻¹
α = 100.751 (5)°	T = 298 K
β = 112.010 (5)°	Block, colorless
γ = 102.318 (5)°	0.23 × 0.20 × 0.18 mm
V = 1390.1 (10) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6236 independent reflections
Radiation source: fine-focus sealed tube	5434 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.885, T_max = 0.908	k = −14→15
13533 measured reflections	l = −17→17

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0863P)² + 0.3678P] where P = (F_o² + 2F_c²)/3
6236 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.55 e Å⁻³
6 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O	γ = 102.318 (5)°
M_r = 648.49	V = 1390.1 (10) Å³
Triclinic, P1	Z = 2
a = 10.208 (5) Å	Mo Kα radiation
b = 11.915 (5) Å	µ = 0.55 mm⁻¹
c = 13.202 (5) Å	T = 298 K
α = 100.751 (5)°	0.23 × 0.20 × 0.18 mm
β = 112.010 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6236 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5434 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.908	R_int = 0.031
13533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	6 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
6236 reflections	Δρ_min = −0.35 e Å⁻³
407 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry codes: (i) x−1, y−1, z; (ii) −x+2, −y+1, −z+1; (iii) x+1, y+1, z.

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.90	1.83	2.716 (3)	169

Symmetry codes: (i) x−1, y−1, z; (iv) x−1, y−2, z.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O
M_r	648.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.208 (5), 11.915 (5), 13.202 (5)
α, β, γ (°)	100.751 (5), 112.010 (5), 102.318 (5)
V (Å³)	1390.1 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.23 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.885, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	13533, 6236, 5434
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.129, 1.05
No. of reflections	6236
No. of parameters	407
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) x−1, y−2, z.

Acknowledgements

The authors thank Jilin Normal University for supporting this work.

References

An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Xiao, D.-R., Wang, E.-B., An, H.-Y., Su, Z.-M., Li, Y.-G., Gao, L., Sun, C.-Y. & Xu, L. (2005). Chem. Eur. J. 11, 6673–6686. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.