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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1092.
Published online 2009 August 19. doi:  10.1107/S1600536809031948
PMCID: PMC2970155

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

Abstract

The title compound, {[Mn2(C7H3NO4)2(C2H5OH)(H2O)2]·H2O}n, is a three-dimensional polymer. There are two symmetry-independent MnII centres with different coordination environments: one MnII atom is coordinated by four O atoms from four ligands and two N atoms from two ligands, the other MnII 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 [triangle]).

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Object name is e-65-m1092-scheme1.jpg

Experimental

Crystal data

  • [Mn2(C7H3NO4)2(C2H6O)(H2O)2]·H2O
  • M r = 540.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1092-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.124
  • S = 1.04
  • 4623 reflections
  • 310 parameters
  • 10 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.72 e Å−3
  • Δρmin = −0.89 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H)= 1.2Ueq(C). H-atoms bonded to water molecules were located in a different Fourier map and refined isotropically.

Figures

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].

Crystal data

[Mn2(C7H3NO4)2(C2H6O)(H2O)2]·H2OZ = 2
Mr = 540.20F(000) = 548
Triclinic, P1Dx = 1.835 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4972 (3) ÅCell parameters from 4623 reflections
b = 10.2676 (4) Åθ = 1.7–29.3°
c = 12.6508 (4) ŵ = 1.36 mm1
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

Oxford Diffraction Gemini R Ultra diffractometer4623 independent reflections
Radiation source: fine-focus sealed tube3432 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 29.3°, θmin = 1.7°
ω scansh = −10→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −11→14
Tmin = 0.765, Tmax = 0.876l = −17→16
11238 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0787P)2] where P = (Fo2 + 2Fc2)/3
4623 reflections(Δ/σ)max = 0.001
310 parametersΔρmax = 0.72 e Å3
10 restraintsΔρmin = −0.89 e Å3

Special details

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)

xyzUiso*/Ueq
Mn11.27969 (5)0.49235 (4)0.24918 (3)0.02484 (13)
Mn20.59087 (5)0.85545 (4)0.26515 (3)0.02779 (14)
C10.7656 (3)0.5490 (3)0.4552 (2)0.0231 (5)
C20.7464 (4)0.4128 (3)0.4991 (2)0.0308 (6)
H20.65220.39860.55340.037*
C30.8660 (4)0.2984 (3)0.4627 (3)0.0336 (7)
H30.85220.20740.49000.040*
C41.0063 (4)0.3234 (3)0.3846 (3)0.0336 (7)
H41.08830.24690.36040.040*
C50.9105 (3)0.5653 (3)0.3738 (2)0.0228 (5)
C60.9532 (3)0.7047 (3)0.3163 (2)0.0230 (5)
C70.6300 (3)0.6661 (3)0.5036 (2)0.0247 (6)
C81.2344 (5)0.6470 (3)−0.1599 (3)0.0461 (9)
H81.23220.6728−0.23660.055*
C91.3034 (4)0.5069 (3)−0.1091 (2)0.0262 (6)
C101.3014 (3)0.4728 (3)0.0062 (2)0.0248 (6)
C111.1694 (6)0.7478 (4)−0.0978 (3)0.0575 (11)
H111.12590.8428−0.13170.069*
C121.1699 (5)0.7052 (3)0.0170 (3)0.0510 (10)
H121.12260.77270.06000.061*
C131.3785 (4)0.3243 (3)0.0709 (2)0.0280 (6)
C141.3882 (4)0.4007 (3)−0.1817 (2)0.0247 (6)
C150.1882 (8)0.9931 (7)0.2423 (7)0.112 (2)
H17A0.17391.01260.16500.135*
H17B0.22141.07250.24730.135*
C160.0088 (13)1.0105 (12)0.3108 (9)0.186 (4)
H18A−0.06151.10330.28270.279*
H18B0.01180.99940.38840.279*
H18C−0.03680.93990.30440.279*
N11.0296 (3)0.4528 (2)0.34232 (19)0.0269 (5)
N21.2358 (3)0.5708 (2)0.06771 (19)0.0311 (5)
O10.5328 (3)0.7618 (2)0.44223 (16)0.0346 (5)
O20.6140 (3)0.6560 (2)0.60686 (16)0.0359 (5)
O30.8368 (3)0.8183 (2)0.31103 (17)0.0329 (5)
O90.3290 (3)0.8821 (3)0.2514 (3)0.0522 (7)
O41.1066 (2)0.6962 (2)0.27672 (16)0.0301 (4)
O3W0.5052 (4)1.0585 (2)0.3092 (2)0.0479 (6)
O51.4375 (3)0.2271 (2)0.02105 (17)0.0443 (6)
O61.3777 (3)0.3112 (2)0.17400 (15)0.0346 (5)
O1W0.2771 (5)0.9922 (4)0.5189 (3)0.0725 (9)
O71.3037 (3)0.3305 (2)−0.19511 (16)0.0308 (4)
O81.5393 (3)0.3966 (2)−0.22933 (17)0.0375 (5)
O2W0.6507 (4)0.9652 (3)0.0894 (2)0.0520 (6)
H9A0.316 (3)0.806 (3)0.253 (4)0.078*
H3A0.502 (6)1.1229 (18)0.2557 (19)0.078*
H1A0.224 (6)1.047 (3)0.561 (3)0.078*
H1B0.312 (6)0.911 (3)0.565 (3)0.078*
H3B0.444 (5)1.058 (3)0.367 (2)0.078*
H2B0.575 (4)1.039 (3)0.070 (3)0.078*
H2A0.735 (4)0.957 (5)0.034 (3)0.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0302 (2)0.0226 (2)0.0194 (2)−0.00310 (17)−0.00298 (15)−0.00753 (16)
Mn20.0325 (2)0.0222 (2)0.0268 (2)−0.00084 (18)−0.01131 (17)−0.00549 (17)
C10.0275 (13)0.0246 (14)0.0169 (11)−0.0044 (11)−0.0081 (10)−0.0041 (10)
C20.0356 (16)0.0301 (16)0.0276 (14)−0.0129 (13)−0.0044 (12)−0.0045 (12)
C30.0442 (18)0.0216 (14)0.0356 (15)−0.0107 (13)−0.0084 (13)−0.0044 (12)
C40.0388 (17)0.0234 (15)0.0388 (16)−0.0042 (12)−0.0078 (13)−0.0117 (12)
C50.0274 (13)0.0202 (13)0.0212 (12)−0.0025 (10)−0.0097 (10)−0.0051 (10)
C60.0282 (14)0.0227 (13)0.0202 (12)−0.0050 (11)−0.0074 (10)−0.0078 (10)
C70.0280 (14)0.0244 (14)0.0221 (13)−0.0078 (11)−0.0059 (10)−0.0040 (11)
C80.071 (2)0.0328 (18)0.0285 (15)0.0059 (16)−0.0250 (15)−0.0073 (13)
C90.0315 (14)0.0242 (14)0.0237 (13)−0.0045 (11)−0.0094 (11)−0.0065 (11)
C100.0270 (13)0.0227 (14)0.0240 (13)−0.0031 (11)−0.0061 (10)−0.0071 (10)
C110.094 (3)0.0254 (18)0.0385 (18)0.0162 (18)−0.0316 (19)−0.0071 (15)
C120.080 (3)0.0265 (17)0.0387 (18)0.0139 (16)−0.0243 (17)−0.0165 (14)
C130.0343 (15)0.0239 (14)0.0243 (13)−0.0040 (12)−0.0064 (11)−0.0070 (11)
C140.0335 (15)0.0207 (13)0.0177 (12)−0.0019 (11)−0.0094 (10)−0.0034 (10)
C150.076 (4)0.094 (5)0.180 (7)−0.020 (3)−0.040 (4)−0.038 (5)
C160.156 (9)0.191 (10)0.215 (11)−0.085 (8)−0.053 (8)0.007 (8)
N10.0295 (12)0.0221 (12)0.0276 (11)−0.0033 (9)−0.0053 (9)−0.0078 (9)
N20.0400 (14)0.0230 (12)0.0258 (12)0.0030 (10)−0.0099 (10)−0.0088 (10)
O10.0335 (11)0.0334 (12)0.0268 (10)0.0020 (9)−0.0081 (8)−0.0024 (8)
O20.0414 (12)0.0378 (12)0.0232 (10)0.0020 (10)−0.0093 (8)−0.0110 (9)
O30.0318 (11)0.0210 (10)0.0471 (12)−0.0023 (8)−0.0143 (9)−0.0089 (9)
O90.0416 (13)0.0287 (13)0.0922 (19)0.0047 (10)−0.0303 (13)−0.0227 (13)
O40.0300 (10)0.0247 (10)0.0336 (10)−0.0071 (8)0.0011 (8)−0.0102 (8)
O3W0.0725 (18)0.0252 (12)0.0428 (13)0.0015 (12)−0.0236 (13)−0.0089 (10)
O50.0772 (17)0.0218 (11)0.0275 (11)0.0061 (10)−0.0203 (11)−0.0094 (9)
O60.0564 (14)0.0230 (10)0.0195 (9)0.0006 (9)−0.0126 (9)−0.0058 (8)
O1W0.078 (2)0.083 (2)0.074 (2)−0.0251 (19)−0.0054 (17)−0.0475 (18)
O70.0334 (11)0.0302 (11)0.0317 (10)−0.0053 (9)−0.0095 (8)−0.0120 (9)
O80.0367 (12)0.0396 (12)0.0402 (12)−0.0140 (10)0.0035 (9)−0.0199 (10)
O2W0.0574 (16)0.0420 (15)0.0408 (13)−0.0039 (12)−0.0133 (11)0.0058 (11)

Geometric parameters (Å, °)

Mn1—O8i2.127 (2)C9—C101.392 (4)
Mn1—O62.1612 (19)C9—C141.510 (4)
Mn1—O2ii2.178 (2)C10—N21.339 (3)
Mn1—O42.1874 (19)C10—C131.515 (4)
Mn1—N12.247 (2)C11—C121.386 (5)
Mn1—N22.281 (2)C11—H110.9300
Mn2—O12.1542 (19)C12—N21.333 (4)
Mn2—O3W2.158 (2)C12—H120.9300
Mn2—O7iii2.1653 (19)C13—O51.235 (3)
Mn2—O2W2.184 (2)C13—O61.269 (3)
Mn2—O32.195 (2)C14—O71.244 (3)
Mn2—O92.196 (3)C14—O81.260 (3)
C1—C21.390 (4)C15—O91.353 (6)
C1—C51.406 (4)C15—C161.526 (11)
C1—C71.516 (4)C15—H17A0.9700
C2—C31.382 (4)C15—H17B0.9700
C2—H20.9300C16—H18A0.9600
C3—C41.378 (4)C16—H18B0.9600
C3—H30.9300C16—H18C0.9600
C4—N11.337 (4)O2—Mn1ii2.178 (2)
C4—H40.9300O9—H9A0.821 (19)
C5—N11.344 (3)O3W—H3A0.793 (16)
C5—C61.515 (4)O3W—H3B0.777 (16)
C6—O31.251 (3)O1W—H1A0.827 (18)
C6—O41.252 (3)O1W—H1B0.872 (18)
C7—O21.254 (3)O7—Mn2iii2.1653 (19)
C7—O11.262 (3)O8—Mn1i2.127 (2)
C8—C111.368 (5)O2W—H2B0.833 (18)
C8—C91.383 (4)O2W—H2A0.863 (18)
C8—H80.9300
O8i—Mn1—O6113.83 (8)C8—C9—C10117.8 (2)
O8i—Mn1—O2ii87.96 (9)C8—C9—C14118.9 (2)
O6—Mn1—O2ii84.30 (7)C10—C9—C14123.1 (2)
O8i—Mn1—O480.75 (8)N2—C10—C9122.1 (3)
O6—Mn1—O4155.64 (8)N2—C10—C13114.9 (2)
O2ii—Mn1—O4116.80 (7)C9—C10—C13122.9 (2)
O8i—Mn1—N1146.77 (8)C8—C11—C12118.4 (3)
O6—Mn1—N198.13 (9)C8—C11—H11120.8
O2ii—Mn1—N186.36 (8)C12—C11—H11120.8
O4—Mn1—N172.82 (8)N2—C12—C11122.3 (3)
O8i—Mn1—N296.47 (9)N2—C12—H12118.8
O6—Mn1—N272.70 (8)C11—C12—H12118.8
O2ii—Mn1—N2156.42 (8)O5—C13—O6125.1 (3)
O4—Mn1—N286.78 (8)O5—C13—C10119.0 (2)
N1—Mn1—N2101.68 (9)O6—C13—C10115.9 (2)
O1—Mn2—O3W87.17 (9)O7—C14—O8125.0 (2)
O1—Mn2—O7iii101.72 (8)O7—C14—C9118.8 (2)
O3W—Mn2—O7iii170.69 (9)O8—C14—C9116.0 (2)
O1—Mn2—O2W175.41 (10)O9—C15—C16130.6 (7)
O3W—Mn2—O2W88.54 (10)O9—C15—H17A104.6
O7iii—Mn2—O2W82.49 (9)C16—C15—H17A104.6
O1—Mn2—O380.79 (8)O9—C15—H17B104.6
O3W—Mn2—O389.55 (9)C16—C15—H17B104.6
O7iii—Mn2—O389.15 (8)H17A—C15—H17B105.7
O2W—Mn2—O397.54 (10)C15—C16—H18A109.5
O1—Mn2—O989.22 (10)C15—C16—H18B109.5
O3W—Mn2—O988.39 (10)H18A—C16—H18B109.5
O7iii—Mn2—O994.44 (8)C15—C16—H18C109.5
O2W—Mn2—O992.30 (11)H18A—C16—H18C109.5
O3—Mn2—O9169.89 (10)H18B—C16—H18C109.5
C2—C1—C5117.7 (2)C4—N1—C5119.6 (2)
C2—C1—C7116.3 (2)C4—N1—Mn1123.72 (19)
C5—C1—C7125.9 (2)C5—N1—Mn1115.42 (18)
C3—C2—C1120.6 (3)C12—N2—C10119.0 (2)
C3—C2—H2119.7C12—N2—Mn1125.7 (2)
C1—C2—H2119.7C10—N2—Mn1114.86 (18)
C4—C3—C2117.9 (3)C7—O1—Mn2128.11 (17)
C4—C3—H3121.1C7—O2—Mn1ii138.53 (18)
C2—C3—H3121.1C6—O3—Mn2125.46 (18)
N1—C4—C3122.9 (3)C15—O9—Mn2134.9 (3)
N1—C4—H4118.6C15—O9—H9A114.7 (19)
C3—C4—H4118.6Mn2—O9—H9A110.5 (19)
N1—C5—C1121.3 (2)C6—O4—Mn1119.19 (17)
N1—C5—C6113.3 (2)Mn2—O3W—H3A112.5 (18)
C1—C5—C6125.5 (2)Mn2—O3W—H3B112.7 (18)
O3—C6—O4124.6 (3)H3A—O3W—H3B127 (3)
O3—C6—C5119.3 (2)C13—O6—Mn1121.35 (17)
O4—C6—C5116.0 (2)H1A—O1W—H1B103 (3)
O2—C7—O1123.2 (2)C14—O7—Mn2iii124.82 (17)
O2—C7—C1116.6 (2)C14—O8—Mn1i138.76 (18)
O1—C7—C1120.0 (2)Mn2—O2W—H2B113 (3)
C11—C8—C9120.3 (3)Mn2—O2W—H2A137 (3)
C11—C8—H8119.9H2B—O2W—H2A109 (3)
C9—C8—H8119.9
C5—C1—C2—C3−0.4 (4)C9—C10—N2—Mn1−172.4 (2)
C7—C1—C2—C3−178.2 (3)C13—C10—N2—Mn15.5 (3)
C1—C2—C3—C42.0 (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—N1175.2 (3)O4—Mn1—N2—C1216.5 (3)
C2—C1—C5—C6179.8 (2)N1—Mn1—N2—C1288.2 (3)
C7—C1—C5—C6−2.6 (4)O8i—Mn1—N2—C10108.1 (2)
N1—C5—C6—O3158.8 (2)O6—Mn1—N2—C10−4.9 (2)
C1—C5—C6—O3−23.2 (4)O2ii—Mn1—N2—C108.3 (4)
N1—C5—C6—O4−21.0 (3)O4—Mn1—N2—C10−171.6 (2)
C1—C5—C6—O4156.9 (3)N1—Mn1—N2—C10−99.8 (2)
C2—C1—C7—O261.3 (4)O2—C7—O1—Mn2150.7 (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—O168.6 (4)O7iii—Mn2—O1—C753.2 (3)
C11—C8—C9—C101.0 (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—C7147.5 (2)
C14—C9—C10—N2175.3 (3)O1—C7—O2—Mn1ii171.5 (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—Mn2134.9 (2)
C9—C8—C11—C12−1.9 (7)C5—C6—O3—Mn2−44.9 (3)
C8—C11—C12—N22.0 (7)O1—Mn2—O3—C685.2 (2)
N2—C10—C13—O5178.0 (3)O3W—Mn2—O3—C6172.4 (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—O6175.3 (3)O9—Mn2—O3—C694.2 (5)
C8—C9—C14—O7−94.3 (4)C16—C15—O9—Mn2−127.9 (8)
C10—C9—C14—O790.4 (3)O1—Mn2—O9—C15103.6 (6)
C8—C9—C14—O882.0 (4)O3W—Mn2—O9—C1516.4 (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—Mn1164.6 (2)O3—Mn2—O9—C1594.7 (7)
C1—C5—N1—C43.5 (4)O3—C6—O4—Mn1−162.1 (2)
C6—C5—N1—C4−178.5 (2)C5—C6—O4—Mn117.7 (3)
C1—C5—N1—Mn1−164.02 (19)O8i—Mn1—O4—C6−167.4 (2)
C6—C5—N1—Mn114.0 (3)O6—Mn1—O4—C663.3 (3)
O8i—Mn1—N1—C4−132.7 (2)O2ii—Mn1—O4—C6−84.4 (2)
O6—Mn1—N1—C431.7 (2)N1—Mn1—O4—C6−7.78 (19)
O2ii—Mn1—N1—C4−52.0 (2)N2—Mn1—O4—C695.5 (2)
O4—Mn1—N1—C4−171.6 (2)O5—C13—O6—Mn1177.4 (3)
N2—Mn1—N1—C4105.6 (2)C10—C13—O6—Mn1−2.1 (3)
O8i—Mn1—N1—C534.2 (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—C5114.9 (2)O4—Mn1—O6—C1337.5 (3)
O4—Mn1—N1—C5−4.62 (18)N1—Mn1—O6—C13103.5 (2)
N2—Mn1—N1—C5−87.50 (19)N2—Mn1—O6—C133.7 (2)
C11—C12—N2—C10−1.1 (6)O8—C14—O7—Mn2iii17.6 (4)
C11—C12—N2—Mn1170.5 (3)C9—C14—O7—Mn2iii−166.56 (17)
C9—C10—N2—C120.2 (5)O7—C14—O8—Mn1i170.8 (2)
C13—C10—N2—C12178.0 (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, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···O3iv0.83 (2)2.29 (3)3.083 (3)161 (5)
O1W—H1B···O10.87 (2)2.51 (4)2.847 (4)104 (3)
O1W—H1B···O3Wiv0.87 (2)2.63 (5)3.034 (4)109 (4)
O2W—H2B···O5v0.83 (2)1.91 (2)2.730 (3)168 (5)
O3W—H3B···O1W0.78 (2)2.14 (2)2.893 (4)162 (3)
O3W—H3A···O6v0.79 (2)1.99 (2)2.699 (3)150 (4)
O9—H9A···O8iii0.82 (2)2.10 (3)2.776 (3)140 (3)
O9—H9A···O4vi0.82 (2)2.32 (2)3.006 (3)142 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5015).

References

  • Li, L.-J. & Li, Y. (2004). J. Mol. Struct. pp. 199–203.
  • Oxford Diffraction (2006). CrysAlis RED and CrysAlis CCD Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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