Poly[[diaqua­(ethanol)bis­(μ3-pyridine-2,3-dicarboxyl­ato)dimanganese(II)] monohydrate]

Zhao, Y.-Q.

doi:10.1107/S1600536809031948

metal-organic compounds

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Volume 65| Part 9| September 2009| Page m1092

doi:10.1107/S1600536809031948

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Poly[[diaqua(ethanol)bis(μ₃-pyridine-2,3-dicarboxylato)dimanganese(II)] monohydrate]

Yan-Qing Zhao ^a ^*

^aDepartment of Chemistry, Liaoning Medical University, Jinzhou 121001, People's Republic of China
^*Correspondence e-mail: wuhua2009@yahoo.com.cn

(Received 18 July 2009; accepted 12 August 2009; online 19 August 2009)

The title compound, {[Mn₂(C₇H₃NO₄)₂(C₂H₅OH)(H₂O)₂]·H₂O}_n, is a three-dimensional polymer. There are two symmetry-independent Mn^II centres with different coordination environments: one Mn^II atom is coordinated by four O atoms from four ligands and two N atoms from two ligands, the other Mn^II atom is coordinated by three O atoms from two ligands, two water O atoms and the O atom of an ethanol molecule. The crystal structure is stabilized by O—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Li & Li (2004 ).

Experimental

Crystal data

[Mn₂(C₇H₃NO₄)₂(C₂H₆O)(H₂O)₂]·H₂O
M_r = 540.20
Triclinic, $[P \overline 1]$
a = 8.4972 (3) Å
b = 10.2676 (4) Å
c = 12.6508 (4) Å
α = 72.661 (3)°
β = 74.859 (3)°
γ = 70.588 (3)°
V = 977.43 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 293 K
0.34 × 0.23 × 0.19 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.765, T_max = 0.876 (expected range = 0.674–0.772)
11238 measured reflections
4623 independent reflections
3432 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.124
S = 1.04
4623 reflections
310 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O3ⁱ	0.827 (18)	2.29 (3)	3.083 (3)	161 (5)
O1W—H1B⋯O1	0.872 (18)	2.51 (4)	2.847 (4)	104 (3)
O1W—H1B⋯O3Wⁱ	0.872 (18)	2.63 (5)	3.034 (4)	109 (4)
O2W—H2B⋯O5ⁱⁱ	0.833 (18)	1.91 (2)	2.730 (3)	168 (5)
O3W—H3B⋯O1W	0.777 (16)	2.14 (2)	2.893 (4)	162 (3)
O3W—H3A⋯O6ⁱⁱ	0.793 (16)	1.99 (2)	2.699 (3)	150 (4)
O9—H9A⋯O8ⁱⁱⁱ	0.821 (19)	2.10 (3)	2.776 (3)	140 (3)
O9—H9A⋯O4^iv	0.821 (19)	2.319 (18)	3.006 (3)	142 (3)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y+1, z; (iii) -x+2, -y+1, -z; (iv) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031948/bt5015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031948/bt5015Isup2.hkl

checkCIF report

Comment top

The title compound possesses two crystallographically unique manganese cations (Fig. 1, Table 1). The Mn(1) cation :is coordinated by four oxygen atoms from four L ligands and two N atoms from two L ligands. Mn(2) cation is coordinated by three oxygen atoms from two L ligands, two water molecules and one ethanol molecule . The Mn—O and Mn—N distances are within the normal range observed in the structure of Li & Li (2004). In the title compound, the manganese centres are bridged by L ligands to form an infinite two-dimensional layer structure. Further, the water molecules and ethanol are involved in formation of hydrogen-bonding interations, leading to a three-dimensional structure.

Related literature top

For a relatedstructure, see: Li & Li (2004).

Experimental top

A mixture of pyridine-2,3-dicarboxylic acid (0.05 g, 0.3 mmol), MnAc₂.4H₂O (0.07 g, 0.3 mmol), EtOH (3 ml) and H₂O (7 ml) was sealed in a 17 ml Teflon-lined stainless-steel cotainer. The container was heated to 140 °C and held at this temperature for 72 h. It was then cooled to room temperature at a rate of 10 °C.h^-1. The colorless blocks were collected in 35% yield.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Anisotropic displacement ellipsoid (30%) plot of the title compound showing the coordination environment around the Mn atoms. [symmetry code: (A) -x + 3, -y + 1, -z; (B) -x + 2, -y + 1,-z + 1; (c) -x + 2, -y + 1, -z].

Poly[[diaqua(ethanol)bis(µ₃-pyridine-2,3-dicarboxylato)dimanganese(II)] monohydrate] top

Crystal data top

[Mn₂(C₇H₃NO₄)₂(C₂H₆O)(H₂O)₂]·H₂O	Z = 2
M_r = 540.20	F(000) = 548
Triclinic, P1	D_x = 1.835 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4972 (3) Å	Cell parameters from 4623 reflections
b = 10.2676 (4) Å	θ = 1.7–29.3°
c = 12.6508 (4) Å	µ = 1.36 mm⁻¹
α = 72.661 (3)°	T = 293 K
β = 74.859 (3)°	Block, colorless
γ = 70.588 (3)°	0.34 × 0.23 × 0.19 mm
V = 977.43 (6) Å³

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	4623 independent reflections
Radiation source: fine-focus sealed tube	3432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.3°, θ_min = 1.7°
ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −11→14
T_min = 0.765, T_max = 0.876	l = −17→16
11238 measured reflections

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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0787P)²] where P = (F_o² + 2F_c²)/3
4623 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 0.72 e Å⁻³
10 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Mn₂(C₇H₃NO₄)₂(C₂H₆O)(H₂O)₂]·H₂O	γ = 70.588 (3)°
M_r = 540.20	V = 977.43 (6) Å³
Triclinic, P1	Z = 2
a = 8.4972 (3) Å	Mo Kα radiation
b = 10.2676 (4) Å	µ = 1.36 mm⁻¹
c = 12.6508 (4) Å	T = 293 K
α = 72.661 (3)°	0.34 × 0.23 × 0.19 mm
β = 74.859 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	4623 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	3432 reflections with I > 2σ(I)
T_min = 0.765, T_max = 0.876	R_int = 0.023
11238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	10 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.72 e Å⁻³
4623 reflections	Δρ_min = −0.89 e Å⁻³
310 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
Mn1	1.27969 (5)	0.49235 (4)	0.24918 (3)	0.02484 (13)
Mn2	0.59087 (5)	0.85545 (4)	0.26515 (3)	0.02779 (14)
C1	0.7656 (3)	0.5490 (3)	0.4552 (2)	0.0231 (5)
C2	0.7464 (4)	0.4128 (3)	0.4991 (2)	0.0308 (6)
H2	0.6522	0.3986	0.5534	0.037*
C3	0.8660 (4)	0.2984 (3)	0.4627 (3)	0.0336 (7)
H3	0.8522	0.2074	0.4900	0.040*
C4	1.0063 (4)	0.3234 (3)	0.3846 (3)	0.0336 (7)
H4	1.0883	0.2469	0.3604	0.040*
C5	0.9105 (3)	0.5653 (3)	0.3738 (2)	0.0228 (5)
C6	0.9532 (3)	0.7047 (3)	0.3163 (2)	0.0230 (5)
C7	0.6300 (3)	0.6661 (3)	0.5036 (2)	0.0247 (6)
C8	1.2344 (5)	0.6470 (3)	−0.1599 (3)	0.0461 (9)
H8	1.2322	0.6728	−0.2366	0.055*
C9	1.3034 (4)	0.5069 (3)	−0.1091 (2)	0.0262 (6)
C10	1.3014 (3)	0.4728 (3)	0.0062 (2)	0.0248 (6)
C11	1.1694 (6)	0.7478 (4)	−0.0978 (3)	0.0575 (11)
H11	1.1259	0.8428	−0.1317	0.069*
C12	1.1699 (5)	0.7052 (3)	0.0170 (3)	0.0510 (10)
H12	1.1226	0.7727	0.0600	0.061*
C13	1.3785 (4)	0.3243 (3)	0.0709 (2)	0.0280 (6)
C14	1.3882 (4)	0.4007 (3)	−0.1817 (2)	0.0247 (6)
C15	0.1882 (8)	0.9931 (7)	0.2423 (7)	0.112 (2)
H17A	0.1739	1.0126	0.1650	0.135*
H17B	0.2214	1.0725	0.2473	0.135*
C16	0.0088 (13)	1.0105 (12)	0.3108 (9)	0.186 (4)
H18A	−0.0615	1.1033	0.2827	0.279*
H18B	0.0118	0.9994	0.3884	0.279*
H18C	−0.0368	0.9399	0.3044	0.279*
N1	1.0296 (3)	0.4528 (2)	0.34232 (19)	0.0269 (5)
N2	1.2358 (3)	0.5708 (2)	0.06771 (19)	0.0311 (5)
O1	0.5328 (3)	0.7618 (2)	0.44223 (16)	0.0346 (5)
O2	0.6140 (3)	0.6560 (2)	0.60686 (16)	0.0359 (5)
O3	0.8368 (3)	0.8183 (2)	0.31103 (17)	0.0329 (5)
O9	0.3290 (3)	0.8821 (3)	0.2514 (3)	0.0522 (7)
O4	1.1066 (2)	0.6962 (2)	0.27672 (16)	0.0301 (4)
O3W	0.5052 (4)	1.0585 (2)	0.3092 (2)	0.0479 (6)
O5	1.4375 (3)	0.2271 (2)	0.02105 (17)	0.0443 (6)
O6	1.3777 (3)	0.3112 (2)	0.17400 (15)	0.0346 (5)
O1W	0.2771 (5)	0.9922 (4)	0.5189 (3)	0.0725 (9)
O7	1.3037 (3)	0.3305 (2)	−0.19511 (16)	0.0308 (4)
O8	1.5393 (3)	0.3966 (2)	−0.22933 (17)	0.0375 (5)
O2W	0.6507 (4)	0.9652 (3)	0.0894 (2)	0.0520 (6)
H9A	0.316 (3)	0.806 (3)	0.253 (4)	0.078*
H3A	0.502 (6)	1.1229 (18)	0.2557 (19)	0.078*
H1A	0.224 (6)	1.047 (3)	0.561 (3)	0.078*
H1B	0.312 (6)	0.911 (3)	0.565 (3)	0.078*
H3B	0.444 (5)	1.058 (3)	0.367 (2)	0.078*
H2B	0.575 (4)	1.039 (3)	0.070 (3)	0.078*
H2A	0.735 (4)	0.957 (5)	0.034 (3)	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0302 (2)	0.0226 (2)	0.0194 (2)	−0.00310 (17)	−0.00298 (15)	−0.00753 (16)
Mn2	0.0325 (2)	0.0222 (2)	0.0268 (2)	−0.00084 (18)	−0.01131 (17)	−0.00549 (17)
C1	0.0275 (13)	0.0246 (14)	0.0169 (11)	−0.0044 (11)	−0.0081 (10)	−0.0041 (10)
C2	0.0356 (16)	0.0301 (16)	0.0276 (14)	−0.0129 (13)	−0.0044 (12)	−0.0045 (12)
C3	0.0442 (18)	0.0216 (14)	0.0356 (15)	−0.0107 (13)	−0.0084 (13)	−0.0044 (12)
C4	0.0388 (17)	0.0234 (15)	0.0388 (16)	−0.0042 (12)	−0.0078 (13)	−0.0117 (12)
C5	0.0274 (13)	0.0202 (13)	0.0212 (12)	−0.0025 (10)	−0.0097 (10)	−0.0051 (10)
C6	0.0282 (14)	0.0227 (13)	0.0202 (12)	−0.0050 (11)	−0.0074 (10)	−0.0078 (10)
C7	0.0280 (14)	0.0244 (14)	0.0221 (13)	−0.0078 (11)	−0.0059 (10)	−0.0040 (11)
C8	0.071 (2)	0.0328 (18)	0.0285 (15)	0.0059 (16)	−0.0250 (15)	−0.0073 (13)
C9	0.0315 (14)	0.0242 (14)	0.0237 (13)	−0.0045 (11)	−0.0094 (11)	−0.0065 (11)
C10	0.0270 (13)	0.0227 (14)	0.0240 (13)	−0.0031 (11)	−0.0061 (10)	−0.0071 (10)
C11	0.094 (3)	0.0254 (18)	0.0385 (18)	0.0162 (18)	−0.0316 (19)	−0.0071 (15)
C12	0.080 (3)	0.0265 (17)	0.0387 (18)	0.0139 (16)	−0.0243 (17)	−0.0165 (14)
C13	0.0343 (15)	0.0239 (14)	0.0243 (13)	−0.0040 (12)	−0.0064 (11)	−0.0070 (11)
C14	0.0335 (15)	0.0207 (13)	0.0177 (12)	−0.0019 (11)	−0.0094 (10)	−0.0034 (10)
C15	0.076 (4)	0.094 (5)	0.180 (7)	−0.020 (3)	−0.040 (4)	−0.038 (5)
C16	0.156 (9)	0.191 (10)	0.215 (11)	−0.085 (8)	−0.053 (8)	0.007 (8)
N1	0.0295 (12)	0.0221 (12)	0.0276 (11)	−0.0033 (9)	−0.0053 (9)	−0.0078 (9)
N2	0.0400 (14)	0.0230 (12)	0.0258 (12)	0.0030 (10)	−0.0099 (10)	−0.0088 (10)
O1	0.0335 (11)	0.0334 (12)	0.0268 (10)	0.0020 (9)	−0.0081 (8)	−0.0024 (8)
O2	0.0414 (12)	0.0378 (12)	0.0232 (10)	0.0020 (10)	−0.0093 (8)	−0.0110 (9)
O3	0.0318 (11)	0.0210 (10)	0.0471 (12)	−0.0023 (8)	−0.0143 (9)	−0.0089 (9)
O9	0.0416 (13)	0.0287 (13)	0.0922 (19)	0.0047 (10)	−0.0303 (13)	−0.0227 (13)
O4	0.0300 (10)	0.0247 (10)	0.0336 (10)	−0.0071 (8)	0.0011 (8)	−0.0102 (8)
O3W	0.0725 (18)	0.0252 (12)	0.0428 (13)	0.0015 (12)	−0.0236 (13)	−0.0089 (10)
O5	0.0772 (17)	0.0218 (11)	0.0275 (11)	0.0061 (10)	−0.0203 (11)	−0.0094 (9)
O6	0.0564 (14)	0.0230 (10)	0.0195 (9)	0.0006 (9)	−0.0126 (9)	−0.0058 (8)
O1W	0.078 (2)	0.083 (2)	0.074 (2)	−0.0251 (19)	−0.0054 (17)	−0.0475 (18)
O7	0.0334 (11)	0.0302 (11)	0.0317 (10)	−0.0053 (9)	−0.0095 (8)	−0.0120 (9)
O8	0.0367 (12)	0.0396 (12)	0.0402 (12)	−0.0140 (10)	0.0035 (9)	−0.0199 (10)
O2W	0.0574 (16)	0.0420 (15)	0.0408 (13)	−0.0039 (12)	−0.0133 (11)	0.0058 (11)

Geometric parameters (Å, º) top

Mn1—O8ⁱ	2.127 (2)	C9—C10	1.392 (4)
Mn1—O6	2.1612 (19)	C9—C14	1.510 (4)
Mn1—O2ⁱⁱ	2.178 (2)	C10—N2	1.339 (3)
Mn1—O4	2.1874 (19)	C10—C13	1.515 (4)
Mn1—N1	2.247 (2)	C11—C12	1.386 (5)
Mn1—N2	2.281 (2)	C11—H11	0.9300
Mn2—O1	2.1542 (19)	C12—N2	1.333 (4)
Mn2—O3W	2.158 (2)	C12—H12	0.9300
Mn2—O7ⁱⁱⁱ	2.1653 (19)	C13—O5	1.235 (3)
Mn2—O2W	2.184 (2)	C13—O6	1.269 (3)
Mn2—O3	2.195 (2)	C14—O7	1.244 (3)
Mn2—O9	2.196 (3)	C14—O8	1.260 (3)
C1—C2	1.390 (4)	C15—O9	1.353 (6)
C1—C5	1.406 (4)	C15—C16	1.526 (11)
C1—C7	1.516 (4)	C15—H17A	0.9700
C2—C3	1.382 (4)	C15—H17B	0.9700
C2—H2	0.9300	C16—H18A	0.9600
C3—C4	1.378 (4)	C16—H18B	0.9600
C3—H3	0.9300	C16—H18C	0.9600
C4—N1	1.337 (4)	O2—Mn1ⁱⁱ	2.178 (2)
C4—H4	0.9300	O9—H9A	0.821 (19)
C5—N1	1.344 (3)	O3W—H3A	0.793 (16)
C5—C6	1.515 (4)	O3W—H3B	0.777 (16)
C6—O3	1.251 (3)	O1W—H1A	0.827 (18)
C6—O4	1.252 (3)	O1W—H1B	0.872 (18)
C7—O2	1.254 (3)	O7—Mn2ⁱⁱⁱ	2.1653 (19)
C7—O1	1.262 (3)	O8—Mn1ⁱ	2.127 (2)
C8—C11	1.368 (5)	O2W—H2B	0.833 (18)
C8—C9	1.383 (4)	O2W—H2A	0.863 (18)
C8—H8	0.9300

O8ⁱ—Mn1—O6	113.83 (8)	C8—C9—C10	117.8 (2)
O8ⁱ—Mn1—O2ⁱⁱ	87.96 (9)	C8—C9—C14	118.9 (2)
O6—Mn1—O2ⁱⁱ	84.30 (7)	C10—C9—C14	123.1 (2)
O8ⁱ—Mn1—O4	80.75 (8)	N2—C10—C9	122.1 (3)
O6—Mn1—O4	155.64 (8)	N2—C10—C13	114.9 (2)
O2ⁱⁱ—Mn1—O4	116.80 (7)	C9—C10—C13	122.9 (2)
O8ⁱ—Mn1—N1	146.77 (8)	C8—C11—C12	118.4 (3)
O6—Mn1—N1	98.13 (9)	C8—C11—H11	120.8
O2ⁱⁱ—Mn1—N1	86.36 (8)	C12—C11—H11	120.8
O4—Mn1—N1	72.82 (8)	N2—C12—C11	122.3 (3)
O8ⁱ—Mn1—N2	96.47 (9)	N2—C12—H12	118.8
O6—Mn1—N2	72.70 (8)	C11—C12—H12	118.8
O2ⁱⁱ—Mn1—N2	156.42 (8)	O5—C13—O6	125.1 (3)
O4—Mn1—N2	86.78 (8)	O5—C13—C10	119.0 (2)
N1—Mn1—N2	101.68 (9)	O6—C13—C10	115.9 (2)
O1—Mn2—O3W	87.17 (9)	O7—C14—O8	125.0 (2)
O1—Mn2—O7ⁱⁱⁱ	101.72 (8)	O7—C14—C9	118.8 (2)
O3W—Mn2—O7ⁱⁱⁱ	170.69 (9)	O8—C14—C9	116.0 (2)
O1—Mn2—O2W	175.41 (10)	O9—C15—C16	130.6 (7)
O3W—Mn2—O2W	88.54 (10)	O9—C15—H17A	104.6
O7ⁱⁱⁱ—Mn2—O2W	82.49 (9)	C16—C15—H17A	104.6
O1—Mn2—O3	80.79 (8)	O9—C15—H17B	104.6
O3W—Mn2—O3	89.55 (9)	C16—C15—H17B	104.6
O7ⁱⁱⁱ—Mn2—O3	89.15 (8)	H17A—C15—H17B	105.7
O2W—Mn2—O3	97.54 (10)	C15—C16—H18A	109.5
O1—Mn2—O9	89.22 (10)	C15—C16—H18B	109.5
O3W—Mn2—O9	88.39 (10)	H18A—C16—H18B	109.5
O7ⁱⁱⁱ—Mn2—O9	94.44 (8)	C15—C16—H18C	109.5
O2W—Mn2—O9	92.30 (11)	H18A—C16—H18C	109.5
O3—Mn2—O9	169.89 (10)	H18B—C16—H18C	109.5
C2—C1—C5	117.7 (2)	C4—N1—C5	119.6 (2)
C2—C1—C7	116.3 (2)	C4—N1—Mn1	123.72 (19)
C5—C1—C7	125.9 (2)	C5—N1—Mn1	115.42 (18)
C3—C2—C1	120.6 (3)	C12—N2—C10	119.0 (2)
C3—C2—H2	119.7	C12—N2—Mn1	125.7 (2)
C1—C2—H2	119.7	C10—N2—Mn1	114.86 (18)
C4—C3—C2	117.9 (3)	C7—O1—Mn2	128.11 (17)
C4—C3—H3	121.1	C7—O2—Mn1ⁱⁱ	138.53 (18)
C2—C3—H3	121.1	C6—O3—Mn2	125.46 (18)
N1—C4—C3	122.9 (3)	C15—O9—Mn2	134.9 (3)
N1—C4—H4	118.6	C15—O9—H9A	114.7 (19)
C3—C4—H4	118.6	Mn2—O9—H9A	110.5 (19)
N1—C5—C1	121.3 (2)	C6—O4—Mn1	119.19 (17)
N1—C5—C6	113.3 (2)	Mn2—O3W—H3A	112.5 (18)
C1—C5—C6	125.5 (2)	Mn2—O3W—H3B	112.7 (18)
O3—C6—O4	124.6 (3)	H3A—O3W—H3B	127 (3)
O3—C6—C5	119.3 (2)	C13—O6—Mn1	121.35 (17)
O4—C6—C5	116.0 (2)	H1A—O1W—H1B	103 (3)
O2—C7—O1	123.2 (2)	C14—O7—Mn2ⁱⁱⁱ	124.82 (17)
O2—C7—C1	116.6 (2)	C14—O8—Mn1ⁱ	138.76 (18)
O1—C7—C1	120.0 (2)	Mn2—O2W—H2B	113 (3)
C11—C8—C9	120.3 (3)	Mn2—O2W—H2A	137 (3)
C11—C8—H8	119.9	H2B—O2W—H2A	109 (3)
C9—C8—H8	119.9

C5—C1—C2—C3	−0.4 (4)	C9—C10—N2—Mn1	−172.4 (2)
C7—C1—C2—C3	−178.2 (3)	C13—C10—N2—Mn1	5.5 (3)
C1—C2—C3—C4	2.0 (5)	O8ⁱ—Mn1—N2—C12	−63.8 (3)
C2—C3—C4—N1	−0.9 (5)	O6—Mn1—N2—C12	−176.8 (3)
C2—C1—C5—N1	−2.4 (4)	O2ⁱⁱ—Mn1—N2—C12	−163.6 (3)
C7—C1—C5—N1	175.2 (3)	O4—Mn1—N2—C12	16.5 (3)
C2—C1—C5—C6	179.8 (2)	N1—Mn1—N2—C12	88.2 (3)
C7—C1—C5—C6	−2.6 (4)	O8ⁱ—Mn1—N2—C10	108.1 (2)
N1—C5—C6—O3	158.8 (2)	O6—Mn1—N2—C10	−4.9 (2)
C1—C5—C6—O3	−23.2 (4)	O2ⁱⁱ—Mn1—N2—C10	8.3 (4)
N1—C5—C6—O4	−21.0 (3)	O4—Mn1—N2—C10	−171.6 (2)
C1—C5—C6—O4	156.9 (3)	N1—Mn1—N2—C10	−99.8 (2)
C2—C1—C7—O2	61.3 (4)	O2—C7—O1—Mn2	150.7 (2)
C5—C1—C7—O2	−116.2 (3)	C1—C7—O1—Mn2	−34.5 (4)
C2—C1—C7—O1	−113.9 (3)	O3W—Mn2—O1—C7	−124.0 (3)
C5—C1—C7—O1	68.6 (4)	O7ⁱⁱⁱ—Mn2—O1—C7	53.2 (3)
C11—C8—C9—C10	1.0 (6)	O2W—Mn2—O1—C7	−103.1 (11)
C11—C8—C9—C14	−174.5 (4)	O3—Mn2—O1—C7	−34.0 (2)
C8—C9—C10—N2	−0.1 (5)	O9—Mn2—O1—C7	147.5 (2)
C14—C9—C10—N2	175.3 (3)	O1—C7—O2—Mn1ⁱⁱ	171.5 (2)
C8—C9—C10—C13	−177.8 (3)	C1—C7—O2—Mn1ⁱⁱ	−3.5 (4)
C14—C9—C10—C13	−2.4 (4)	O4—C6—O3—Mn2	134.9 (2)
C9—C8—C11—C12	−1.9 (7)	C5—C6—O3—Mn2	−44.9 (3)
C8—C11—C12—N2	2.0 (7)	O1—Mn2—O3—C6	85.2 (2)
N2—C10—C13—O5	178.0 (3)	O3W—Mn2—O3—C6	172.4 (2)
C9—C10—C13—O5	−4.2 (5)	O7ⁱⁱⁱ—Mn2—O3—C6	−16.8 (2)
N2—C10—C13—O6	−2.6 (4)	O2W—Mn2—O3—C6	−99.1 (2)
C9—C10—C13—O6	175.3 (3)	O9—Mn2—O3—C6	94.2 (5)
C8—C9—C14—O7	−94.3 (4)	C16—C15—O9—Mn2	−127.9 (8)
C10—C9—C14—O7	90.4 (3)	O1—Mn2—O9—C15	103.6 (6)
C8—C9—C14—O8	82.0 (4)	O3W—Mn2—O9—C15	16.4 (6)
C10—C9—C14—O8	−93.4 (3)	O7ⁱⁱⁱ—Mn2—O9—C15	−154.7 (6)
C3—C4—N1—C5	−1.8 (4)	O2W—Mn2—O9—C15	−72.1 (6)
C3—C4—N1—Mn1	164.6 (2)	O3—Mn2—O9—C15	94.7 (7)
C1—C5—N1—C4	3.5 (4)	O3—C6—O4—Mn1	−162.1 (2)
C6—C5—N1—C4	−178.5 (2)	C5—C6—O4—Mn1	17.7 (3)
C1—C5—N1—Mn1	−164.02 (19)	O8ⁱ—Mn1—O4—C6	−167.4 (2)
C6—C5—N1—Mn1	14.0 (3)	O6—Mn1—O4—C6	63.3 (3)
O8ⁱ—Mn1—N1—C4	−132.7 (2)	O2ⁱⁱ—Mn1—O4—C6	−84.4 (2)
O6—Mn1—N1—C4	31.7 (2)	N1—Mn1—O4—C6	−7.78 (19)
O2ⁱⁱ—Mn1—N1—C4	−52.0 (2)	N2—Mn1—O4—C6	95.5 (2)
O4—Mn1—N1—C4	−171.6 (2)	O5—C13—O6—Mn1	177.4 (3)
N2—Mn1—N1—C4	105.6 (2)	C10—C13—O6—Mn1	−2.1 (3)
O8ⁱ—Mn1—N1—C5	34.2 (3)	O8ⁱ—Mn1—O6—C13	−85.8 (2)
O6—Mn1—N1—C5	−161.41 (19)	O2ⁱⁱ—Mn1—O6—C13	−171.0 (2)
O2ⁱⁱ—Mn1—N1—C5	114.9 (2)	O4—Mn1—O6—C13	37.5 (3)
O4—Mn1—N1—C5	−4.62 (18)	N1—Mn1—O6—C13	103.5 (2)
N2—Mn1—N1—C5	−87.50 (19)	N2—Mn1—O6—C13	3.7 (2)
C11—C12—N2—C10	−1.1 (6)	O8—C14—O7—Mn2ⁱⁱⁱ	17.6 (4)
C11—C12—N2—Mn1	170.5 (3)	C9—C14—O7—Mn2ⁱⁱⁱ	−166.56 (17)
C9—C10—N2—C12	0.2 (5)	O7—C14—O8—Mn1ⁱ	170.8 (2)
C13—C10—N2—C12	178.0 (3)	C9—C14—O8—Mn1ⁱ	−5.2 (4)

Symmetry codes: (i) −x+3, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O3^iv	0.83 (2)	2.29 (3)	3.083 (3)	161 (5)
O1W—H1B···O1	0.87 (2)	2.51 (4)	2.847 (4)	104 (3)
O1W—H1B···O3W^iv	0.87 (2)	2.63 (5)	3.034 (4)	109 (4)
O2W—H2B···O5^v	0.83 (2)	1.91 (2)	2.730 (3)	168 (5)
O3W—H3B···O1W	0.78 (2)	2.14 (2)	2.893 (4)	162 (3)
O3W—H3A···O6^v	0.79 (2)	1.99 (2)	2.699 (3)	150 (4)
O9—H9A···O8ⁱⁱⁱ	0.82 (2)	2.10 (3)	2.776 (3)	140 (3)
O9—H9A···O4^vi	0.82 (2)	2.32 (2)	3.006 (3)	142 (3)

Symmetry codes: (iii) −x+2, −y+1, −z; (iv) −x+1, −y+2, −z+1; (v) x−1, y+1, z; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Mn₂(C₇H₃NO₄)₂(C₂H₆O)(H₂O)₂]·H₂O
M_r	540.20
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4972 (3), 10.2676 (4), 12.6508 (4)
α, β, γ (°)	72.661 (3), 74.859 (3), 70.588 (3)
V (Å³)	977.43 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.34 × 0.23 × 0.19

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.765, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	11238, 4623, 3432
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.124, 1.04
No. of reflections	4623
No. of parameters	310
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.89

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O3ⁱ	0.827 (18)	2.29 (3)	3.083 (3)	161 (5)
O1W—H1B···O1	0.872 (18)	2.51 (4)	2.847 (4)	104 (3)
O1W—H1B···O3Wⁱ	0.872 (18)	2.63 (5)	3.034 (4)	109 (4)
O2W—H2B···O5ⁱⁱ	0.833 (18)	1.91 (2)	2.730 (3)	168 (5)
O3W—H3B···O1W	0.777 (16)	2.14 (2)	2.893 (4)	162 (3)
O3W—H3A···O6ⁱⁱ	0.793 (16)	1.99 (2)	2.699 (3)	150 (4)
O9—H9A···O8ⁱⁱⁱ	0.821 (19)	2.10 (3)	2.776 (3)	140 (3)
O9—H9A···O4^iv	0.821 (19)	2.319 (18)	3.006 (3)	142 (3)

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

Acknowledgements

The authors thank the Science Foundation of Liaoning Medical University for supporting this work.

References

Li, L.-J. & Li, Y. (2004). J. Mol. Struct. pp. 199–203. Web of Science CSD CrossRef Google Scholar
Oxford Diffraction (2006). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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