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Poly[aqua­bis­(μ4-naphthalene-1,4-di­carboxyl­ato)(1,10-phenanthroline-5,6-dione)dimanganese(II)]

aDepartment of Basic Science, Tianjin Agricultural University, Tjianjin 300384, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: congfangdi666@yahoo.com.cn

(Received 1 November 2009; accepted 4 November 2009; online 7 November 2009)

The three-dimensional coordination polymer, [Mn2(C12H6O4)2(C12H6N2O2)(H2O)]n, features a water-coord­inated MnII ion and an N-heterocycle-chelated MnII ion, both in six-coordinate octa­hedral geometries. Of the two rigid dianions, one is bonded to four MnII ions, with each of the O atoms being connected to a different metal ion. The other dianion uses one carboxyl­ate group to chelate to one MnII ion and its other carboxyl­ate group to bind to two MnII ions.

Related literature

For similiar manganese naphthalene-1,4-dicarboxyl­ate polymers, see: Boeckmann et al. (2009[Boeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m421.]); Li et al. (2008[Li, H.-D., Li, X.-Y., Xu, M.-L. & Ng, S. W. (2008). Acta Cryst. E64, m701-m702.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn2(C12H6O4)2(C12H6N2O2)(H2O)]

  • Mr = 766.42

  • Monoclinic, P 21 /c

  • a = 8.4393 (8) Å

  • b = 19.2477 (18) Å

  • c = 19.2504 (19) Å

  • β = 101.781 (1)°

  • V = 3061.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.90 mm−1

  • T = 293 K

  • 0.27 × 0.26 × 0.20 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.794, Tmax = 0.841

  • 16986 measured reflections

  • 6015 independent reflections

  • 4853 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.03

  • 6015 reflections

  • 466 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Selected bond lengths (Å)

Mn1—O1 2.106 (2)
Mn1—O4i 2.137 (2)
Mn1—O5 2.190 (2)
Mn1—O6 2.545 (2)
Mn1—O7ii 2.182 (2)
Mn1—O1W 2.157 (2)
Mn2—O2 2.125 (2)
Mn2—O3iii 2.173 (2)
Mn2—O5 2.192 (2)
Mn2—O8ii 2.104 (2)
Mn2—N1 2.273 (2)
Mn2—N2 2.268 (2)
Symmetry codes: (i) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For similiar manganese naphthalene-1,4-dicarboxylate polymers, see: Boeckmann et al. (2009); Li et al. (2008).

Experimental top

Manganese dichloride tetrahydrate (0.5 mmol, 0.099 g), naphthalene-1,4-dicarboxylic acid (0.5 mmol, 0.108 g), phenanthrene-9,10-dione (0.5 mmol, 0.104 g) and water (12 ml) were heated in a Teflon-lined, stainless-steel Parr bomb at 433 K for 3 days. Yellow crystals were isolated from the cool bomb in 40% yield.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C-H = 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The water H atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85 (1) Å and H···H 1.39 (1) Å; their Uiso values were set to 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of a part of the polymeric three-dimensional structure of Mn2(H2O)(C12H6O4)2(C12H6N2O2) at the 50% probability level; H atoms are drawn as spheres of arbitrary radius. Symmetry codes are given in Table 1.
Poly[aquabis(µ4-naphthalene-1,4-dicarboxylato)(1,10-phenanthroline- 5,6-dione)dimanganese(II)] top
Crystal data top
[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]F(000) = 1552
Mr = 766.42Dx = 1.663 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5446 reflections
a = 8.4393 (8) Åθ = 2.1–25.7°
b = 19.2477 (18) ŵ = 0.90 mm1
c = 19.2504 (19) ÅT = 293 K
β = 101.781 (1)°Block, yellow
V = 3061.1 (5) Å30.27 × 0.26 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer
6015 independent reflections
Radiation source: fine-focus sealed tube4853 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 26.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.794, Tmax = 0.841k = 1523
16986 measured reflectionsl = 2322
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.1115P]
where P = (Fo2 + 2Fc2)/3
6015 reflections(Δ/σ)max = 0.001
466 parametersΔρmax = 0.40 e Å3
3 restraintsΔρmin = 0.24 e Å3
Crystal data top
[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]V = 3061.1 (5) Å3
Mr = 766.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4393 (8) ŵ = 0.90 mm1
b = 19.2477 (18) ÅT = 293 K
c = 19.2504 (19) Å0.27 × 0.26 × 0.20 mm
β = 101.781 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer
6015 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4853 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.841Rint = 0.025
16986 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0363 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.40 e Å3
6015 reflectionsΔρmin = 0.24 e Å3
466 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.67563 (4)0.723418 (17)0.635261 (16)0.02973 (10)
Mn20.32185 (4)0.688473 (16)0.694983 (16)0.02825 (10)
O10.49411 (18)0.71363 (9)0.54284 (8)0.0435 (4)
O20.2654 (2)0.69971 (10)0.58282 (8)0.0491 (4)
O30.09036 (18)0.76369 (9)0.19849 (8)0.0381 (4)
O40.14651 (18)0.76639 (9)0.23115 (8)0.0448 (4)
O50.55827 (18)0.64436 (7)0.68920 (9)0.0371 (4)
O60.7185 (2)0.59280 (10)0.63001 (11)0.0591 (5)
O70.4054 (2)0.32857 (10)0.84788 (10)0.0574 (5)
O80.5400 (2)0.27848 (8)0.77449 (11)0.0557 (5)
O90.0460 (3)0.40503 (13)0.83873 (16)0.1069 (9)
O100.2619 (3)0.45832 (15)0.95212 (15)0.1063 (10)
O1W0.8607 (2)0.75106 (16)0.57777 (10)0.0787 (7)
H1W10.949 (3)0.754 (2)0.6082 (16)0.118*
H1W20.851 (4)0.7853 (14)0.5499 (17)0.118*
N10.1895 (2)0.58539 (10)0.69258 (11)0.0396 (5)
N20.3748 (2)0.64538 (10)0.80699 (10)0.0356 (4)
C10.3440 (3)0.71125 (12)0.53511 (11)0.0334 (5)
C20.2493 (2)0.72461 (11)0.46106 (11)0.0306 (5)
C30.2775 (3)0.68379 (11)0.40590 (11)0.0328 (5)
H30.35020.64700.41510.039*
C40.1973 (2)0.69744 (11)0.33599 (11)0.0303 (5)
H40.21980.67030.29930.036*
C50.0864 (2)0.74994 (12)0.32073 (10)0.0291 (5)
C60.0551 (2)0.79415 (12)0.37652 (11)0.0312 (5)
C70.1407 (2)0.78174 (11)0.44707 (11)0.0310 (5)
C80.1222 (3)0.82974 (13)0.50106 (12)0.0406 (6)
H80.17850.82250.54730.049*
C90.0237 (3)0.88607 (14)0.48629 (14)0.0512 (7)
H90.01490.91740.52210.061*
C100.0644 (3)0.89695 (15)0.41734 (14)0.0543 (7)
H100.13360.93490.40790.065*
C110.0502 (3)0.85250 (13)0.36358 (13)0.0434 (6)
H110.10990.86050.31810.052*
C120.0036 (3)0.76148 (11)0.24480 (11)0.0303 (5)
C130.6211 (3)0.58948 (11)0.66943 (12)0.0335 (5)
C140.5764 (3)0.52226 (11)0.69999 (12)0.0352 (5)
C150.6256 (3)0.51188 (12)0.77124 (13)0.0437 (6)
H150.68300.54670.79900.052*
C160.5917 (3)0.44982 (12)0.80367 (13)0.0410 (6)
H160.63030.44330.85200.049*
C170.5020 (3)0.39879 (11)0.76437 (12)0.0341 (5)
C180.4411 (3)0.40882 (11)0.69041 (12)0.0342 (5)
C190.4819 (3)0.47085 (11)0.65730 (12)0.0347 (5)
C200.4218 (3)0.47993 (14)0.58366 (13)0.0462 (6)
H200.44740.52010.56140.055*
C210.3261 (3)0.43017 (15)0.54474 (14)0.0551 (7)
H210.29030.43610.49610.066*
C220.2825 (3)0.37081 (15)0.57776 (15)0.0556 (7)
H220.21500.33810.55100.067*
C230.3369 (3)0.35979 (13)0.64828 (14)0.0461 (6)
H230.30580.31990.66930.055*
C240.4799 (3)0.33048 (12)0.79864 (13)0.0393 (5)
C250.0982 (3)0.55711 (14)0.63501 (15)0.0518 (7)
H250.08970.58000.59190.062*
C260.0150 (3)0.49487 (16)0.63629 (19)0.0671 (9)
H260.04660.47620.59490.081*
C270.0261 (4)0.46209 (15)0.6996 (2)0.0687 (9)
H270.02830.42040.70190.082*
C280.1182 (3)0.49066 (13)0.76087 (17)0.0523 (7)
C290.1999 (3)0.55246 (11)0.75504 (13)0.0383 (5)
C300.1294 (4)0.45708 (16)0.8302 (2)0.0719 (10)
C310.2429 (3)0.48801 (17)0.89331 (19)0.0677 (9)
C320.3262 (3)0.55354 (14)0.88447 (15)0.0497 (7)
C330.3028 (3)0.58499 (12)0.81738 (13)0.0377 (5)
C340.4268 (4)0.58562 (17)0.94055 (15)0.0600 (8)
H340.44240.56630.98570.072*
C350.5043 (3)0.64632 (16)0.92973 (14)0.0558 (7)
H350.57500.66790.96680.067*
C360.4743 (3)0.67442 (13)0.86218 (13)0.0436 (6)
H360.52610.71560.85480.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02579 (17)0.0373 (2)0.02387 (18)0.00187 (13)0.00003 (13)0.00353 (13)
Mn20.02932 (18)0.02970 (19)0.02565 (18)0.00156 (13)0.00545 (13)0.00262 (13)
O10.0295 (8)0.0699 (12)0.0270 (9)0.0000 (8)0.0040 (7)0.0044 (8)
O20.0406 (9)0.0801 (13)0.0252 (9)0.0001 (9)0.0033 (7)0.0107 (8)
O30.0312 (8)0.0585 (11)0.0239 (8)0.0072 (7)0.0039 (6)0.0004 (7)
O40.0277 (8)0.0786 (13)0.0251 (8)0.0072 (8)0.0019 (6)0.0002 (8)
O50.0374 (8)0.0267 (8)0.0477 (10)0.0047 (6)0.0099 (7)0.0071 (7)
O60.0663 (12)0.0533 (12)0.0682 (13)0.0105 (9)0.0383 (11)0.0109 (9)
O70.0712 (13)0.0504 (11)0.0552 (12)0.0088 (9)0.0237 (10)0.0068 (9)
O80.0668 (12)0.0262 (9)0.0721 (13)0.0113 (8)0.0099 (10)0.0051 (8)
O90.114 (2)0.0741 (17)0.139 (3)0.0251 (15)0.0409 (19)0.0406 (16)
O100.0751 (16)0.128 (2)0.116 (2)0.0035 (15)0.0201 (15)0.0892 (19)
O1W0.0413 (11)0.160 (2)0.0328 (11)0.0267 (13)0.0040 (9)0.0165 (12)
N10.0353 (10)0.0389 (11)0.0448 (12)0.0035 (8)0.0086 (9)0.0023 (9)
N20.0357 (10)0.0387 (11)0.0330 (11)0.0031 (8)0.0083 (8)0.0026 (8)
C10.0356 (12)0.0398 (13)0.0233 (11)0.0000 (9)0.0026 (9)0.0007 (9)
C20.0242 (10)0.0420 (13)0.0235 (11)0.0037 (9)0.0001 (8)0.0032 (9)
C30.0305 (11)0.0364 (13)0.0293 (12)0.0020 (9)0.0007 (9)0.0014 (9)
C40.0304 (11)0.0338 (12)0.0252 (11)0.0024 (9)0.0020 (9)0.0028 (9)
C50.0248 (10)0.0380 (12)0.0226 (11)0.0055 (9)0.0001 (8)0.0018 (9)
C60.0232 (10)0.0442 (13)0.0258 (11)0.0001 (9)0.0037 (8)0.0008 (9)
C70.0240 (10)0.0448 (14)0.0236 (11)0.0022 (9)0.0038 (8)0.0021 (9)
C80.0403 (13)0.0570 (16)0.0241 (12)0.0035 (11)0.0055 (10)0.0014 (10)
C90.0518 (15)0.0654 (18)0.0377 (15)0.0130 (13)0.0122 (12)0.0118 (12)
C100.0486 (15)0.0658 (19)0.0469 (16)0.0253 (13)0.0062 (12)0.0052 (13)
C110.0372 (12)0.0580 (17)0.0318 (13)0.0132 (11)0.0002 (10)0.0000 (11)
C120.0310 (11)0.0355 (12)0.0219 (11)0.0039 (9)0.0004 (9)0.0004 (9)
C130.0337 (11)0.0319 (12)0.0332 (12)0.0033 (9)0.0031 (10)0.0039 (9)
C140.0400 (12)0.0270 (12)0.0389 (13)0.0067 (9)0.0091 (10)0.0036 (9)
C150.0567 (15)0.0306 (13)0.0404 (14)0.0062 (11)0.0019 (12)0.0007 (10)
C160.0550 (15)0.0309 (13)0.0340 (13)0.0014 (11)0.0022 (11)0.0038 (10)
C170.0378 (12)0.0262 (12)0.0384 (13)0.0066 (9)0.0077 (10)0.0020 (9)
C180.0360 (12)0.0272 (12)0.0388 (13)0.0066 (9)0.0062 (10)0.0024 (10)
C190.0380 (12)0.0298 (12)0.0363 (13)0.0097 (9)0.0078 (10)0.0004 (10)
C200.0523 (15)0.0468 (15)0.0387 (14)0.0083 (12)0.0073 (12)0.0026 (11)
C210.0618 (17)0.0634 (19)0.0360 (15)0.0086 (14)0.0007 (13)0.0053 (13)
C220.0544 (16)0.0535 (17)0.0525 (17)0.0014 (13)0.0044 (13)0.0174 (14)
C230.0445 (14)0.0357 (14)0.0539 (16)0.0023 (11)0.0002 (12)0.0077 (11)
C240.0377 (12)0.0315 (13)0.0448 (15)0.0028 (10)0.0008 (11)0.0046 (11)
C250.0448 (14)0.0533 (17)0.0558 (17)0.0035 (12)0.0062 (13)0.0083 (13)
C260.0498 (16)0.0559 (19)0.091 (3)0.0129 (14)0.0027 (16)0.0235 (18)
C270.0528 (17)0.0409 (17)0.112 (3)0.0162 (13)0.0163 (18)0.0035 (18)
C280.0421 (14)0.0373 (14)0.082 (2)0.0015 (11)0.0219 (14)0.0063 (14)
C290.0315 (11)0.0315 (12)0.0556 (16)0.0040 (9)0.0176 (11)0.0029 (11)
C300.0629 (19)0.0480 (18)0.113 (3)0.0073 (15)0.038 (2)0.0318 (18)
C310.0480 (16)0.072 (2)0.089 (2)0.0135 (15)0.0276 (16)0.0460 (19)
C320.0446 (14)0.0553 (17)0.0543 (17)0.0139 (12)0.0216 (13)0.0246 (13)
C330.0342 (12)0.0353 (13)0.0478 (14)0.0081 (10)0.0179 (11)0.0093 (11)
C340.0582 (17)0.080 (2)0.0435 (16)0.0232 (16)0.0148 (14)0.0234 (15)
C350.0564 (17)0.070 (2)0.0379 (15)0.0158 (15)0.0016 (13)0.0003 (13)
C360.0443 (14)0.0463 (15)0.0389 (14)0.0045 (11)0.0057 (11)0.0002 (11)
Geometric parameters (Å, º) top
Mn1—O12.106 (2)C8—C91.361 (4)
Mn1—O4i2.137 (2)C8—H80.93
Mn1—O52.190 (2)C9—C101.398 (4)
Mn1—O62.545 (2)C9—H90.93
Mn1—O7ii2.182 (2)C10—C111.367 (3)
Mn1—O1W2.157 (2)C10—H100.93
Mn2—O22.125 (2)C11—H110.93
Mn2—O3iii2.173 (2)C13—C141.501 (3)
Mn2—O52.192 (2)C14—C151.364 (3)
Mn2—O8ii2.104 (2)C14—C191.422 (3)
Mn2—N12.273 (2)C15—C161.404 (3)
Mn2—N22.268 (2)C15—H150.93
O1—C11.246 (3)C16—C171.370 (3)
O2—C11.258 (3)C16—H160.93
O3—C121.265 (2)C17—C181.425 (3)
O3—Mn2iv2.1733 (15)C17—C241.500 (3)
O4—C121.244 (3)C18—C231.425 (3)
O4—Mn1v2.1371 (15)C18—C191.428 (3)
O5—C131.274 (3)C19—C201.416 (3)
O6—C131.229 (3)C20—C211.373 (4)
O7—C241.240 (3)C20—H200.93
O7—Mn1vi2.1818 (18)C21—C221.393 (4)
O8—C241.254 (3)C21—H210.93
O8—Mn2vi2.1039 (17)C22—C231.358 (4)
O9—C301.254 (4)C22—H220.93
O10—C311.249 (4)C23—H230.93
O1W—H1W10.852 (10)C25—C261.392 (4)
O1W—H1W20.844 (10)C25—H250.93
N1—C251.330 (3)C26—C271.359 (5)
N1—C291.346 (3)C26—H260.93
N2—C361.335 (3)C27—C281.387 (4)
N2—C331.346 (3)C27—H270.93
C1—C21.507 (3)C28—C291.391 (3)
C2—C31.380 (3)C28—C301.469 (4)
C2—C71.421 (3)C29—C331.470 (3)
C3—C41.403 (3)C30—C311.507 (5)
C3—H30.93C31—C321.471 (4)
C4—C51.367 (3)C32—C341.376 (4)
C4—H40.93C32—C331.403 (3)
C5—C61.436 (3)C34—C351.375 (4)
C5—C121.502 (3)C34—H340.93
C6—C71.422 (3)C35—C361.383 (4)
C6—C111.422 (3)C35—H350.93
C7—C81.423 (3)C36—H360.93
O1—Mn1—O4i178.03 (6)O4—C12—O3124.03 (19)
O1—Mn1—O1W93.82 (7)O4—C12—C5117.92 (18)
O4i—Mn1—O1W88.06 (7)O3—C12—C5118.02 (18)
O1—Mn1—O7ii90.73 (7)O6—C13—O5120.8 (2)
O4i—Mn1—O7ii88.43 (7)O6—C13—C14122.7 (2)
O1W—Mn1—O7ii97.43 (10)O5—C13—C14116.39 (19)
O1—Mn1—O590.97 (6)C15—C14—C19119.9 (2)
O4i—Mn1—O587.72 (6)C15—C14—C13118.1 (2)
O1W—Mn1—O5149.28 (9)C19—C14—C13122.0 (2)
O7ii—Mn1—O5112.85 (6)C14—C15—C16121.6 (2)
O8ii—Mn2—O2101.33 (7)C14—C15—H15119.2
O8ii—Mn2—O3iii95.33 (7)C16—C15—H15119.2
O2—Mn2—O3iii88.39 (6)C17—C16—C15120.3 (2)
O8ii—Mn2—O582.81 (7)C17—C16—H16119.9
O2—Mn2—O590.31 (6)C15—C16—H16119.9
O3iii—Mn2—O5177.48 (6)C16—C17—C18120.0 (2)
O8ii—Mn2—N292.59 (7)C16—C17—C24119.4 (2)
O2—Mn2—N2164.37 (7)C18—C17—C24120.4 (2)
O3iii—Mn2—N297.43 (6)C17—C18—C23122.3 (2)
O5—Mn2—N284.37 (6)C17—C18—C19119.3 (2)
O8ii—Mn2—N1165.15 (8)C23—C18—C19118.5 (2)
O2—Mn2—N193.49 (7)C20—C19—C14122.5 (2)
O3iii—Mn2—N185.94 (7)C20—C19—C18118.7 (2)
O5—Mn2—N196.29 (6)C14—C19—C18118.8 (2)
N2—Mn2—N172.58 (7)C21—C20—C19120.7 (2)
C1—O1—Mn1130.60 (14)C21—C20—H20119.6
C1—O2—Mn2135.86 (15)C19—C20—H20119.6
C12—O3—Mn2iv133.60 (14)C20—C21—C22120.3 (3)
C12—O4—Mn1v134.03 (14)C20—C21—H21119.9
C13—O5—Mn1100.28 (13)C22—C21—H21119.9
C13—O5—Mn2140.78 (14)C23—C22—C21121.2 (3)
Mn1—O5—Mn2105.04 (6)C23—C22—H22119.4
C24—O7—Mn1vi111.36 (16)C21—C22—H22119.4
C24—O8—Mn2vi142.85 (18)C22—C23—C18120.6 (3)
Mn1—O1W—H1W1107 (3)C22—C23—H23119.7
Mn1—O1W—H1W2122 (3)C18—C23—H23119.7
H1W1—O1W—H1W2110.1 (17)O7—C24—O8124.5 (2)
C25—N1—C29118.2 (2)O7—C24—C17119.4 (2)
C25—N1—Mn2124.95 (18)O8—C24—C17116.1 (2)
C29—N1—Mn2116.78 (15)N1—C25—C26123.1 (3)
C36—N2—C33118.2 (2)N1—C25—H25118.5
C36—N2—Mn2124.99 (16)C26—C25—H25118.5
C33—N2—Mn2116.75 (15)C27—C26—C25118.2 (3)
O1—C1—O2126.5 (2)C27—C26—H26120.9
O1—C1—C2115.88 (18)C25—C26—H26120.9
O2—C1—C2117.64 (19)C26—C27—C28120.2 (3)
C3—C2—C7120.04 (19)C26—C27—H27119.9
C3—C2—C1119.28 (19)C28—C27—H27119.9
C7—C2—C1120.53 (19)C27—C28—C29118.1 (3)
C2—C3—C4120.4 (2)C27—C28—C30121.3 (3)
C2—C3—H3119.8C29—C28—C30120.6 (3)
C4—C3—H3119.8N1—C29—C28122.1 (2)
C5—C4—C3121.3 (2)N1—C29—C33116.7 (2)
C5—C4—H4119.3C28—C29—C33121.2 (2)
C3—C4—H4119.3O9—C30—C28122.4 (4)
C4—C5—C6119.96 (19)O9—C30—C31119.5 (3)
C4—C5—C12118.68 (19)C28—C30—C31118.1 (3)
C6—C5—C12121.32 (19)O10—C31—C32121.4 (3)
C7—C6—C11118.5 (2)O10—C31—C30119.5 (3)
C7—C6—C5118.63 (19)C32—C31—C30119.1 (3)
C11—C6—C5122.7 (2)C34—C32—C33118.5 (3)
C6—C7—C2119.54 (19)C34—C32—C31121.8 (3)
C6—C7—C8118.6 (2)C33—C32—C31119.7 (3)
C2—C7—C8121.8 (2)N2—C33—C32121.8 (2)
C9—C8—C7121.2 (2)N2—C33—C29117.1 (2)
C9—C8—H8119.4C32—C33—C29121.1 (2)
C7—C8—H8119.4C35—C34—C32119.9 (2)
C8—C9—C10120.1 (2)C35—C34—H34120.0
C8—C9—H9120.0C32—C34—H34120.0
C10—C9—H9120.0C34—C35—C36118.2 (3)
C11—C10—C9120.9 (2)C34—C35—H35120.9
C11—C10—H10119.6C36—C35—H35120.9
C9—C10—H10119.6N2—C36—C35123.3 (3)
C10—C11—C6120.7 (2)N2—C36—H36118.3
C10—C11—H11119.7C35—C36—H36118.3
C6—C11—H11119.7
O1w—Mn1—O1—C1164.4 (2)Mn1—O5—C13—O60.3 (3)
O7ii—Mn1—O1—C166.9 (2)Mn2—O5—C13—O6129.4 (2)
O5—Mn1—O1—C146.0 (2)Mn1—O5—C13—C14176.44 (16)
O8ii—Mn2—O2—C151.2 (3)Mn2—O5—C13—C1453.8 (3)
O3iii—Mn2—O2—C1146.4 (2)O6—C13—C14—C15111.3 (3)
O5—Mn2—O2—C131.5 (2)O5—C13—C14—C1565.5 (3)
N2—Mn2—O2—C1101.3 (3)O6—C13—C14—C1970.4 (3)
N1—Mn2—O2—C1127.8 (2)O5—C13—C14—C19112.9 (2)
O1—Mn1—O5—C1386.84 (14)C19—C14—C15—C163.0 (4)
O4i—Mn1—O5—C1394.63 (14)C13—C14—C15—C16178.6 (2)
O1w—Mn1—O5—C1312.3 (2)C14—C15—C16—C172.5 (4)
O7ii—Mn1—O5—C13178.04 (13)C15—C16—C17—C180.7 (3)
O1—Mn1—O5—Mn262.92 (7)C15—C16—C17—C24174.5 (2)
O4i—Mn1—O5—Mn2115.60 (7)C16—C17—C18—C23175.0 (2)
O1w—Mn1—O5—Mn2162.08 (11)C24—C17—C18—C239.8 (3)
O7ii—Mn1—O5—Mn228.27 (10)C16—C17—C18—C193.3 (3)
O8ii—Mn2—O5—C13172.7 (2)C24—C17—C18—C19171.9 (2)
O2—Mn2—O5—C1371.3 (2)C15—C14—C19—C20177.4 (2)
N2—Mn2—O5—C1394.0 (2)C13—C14—C19—C200.9 (3)
N1—Mn2—O5—C1322.2 (2)C15—C14—C19—C180.3 (3)
O8ii—Mn2—O5—Mn144.29 (8)C13—C14—C19—C18178.62 (19)
O2—Mn2—O5—Mn157.10 (8)C17—C18—C19—C20179.5 (2)
N2—Mn2—O5—Mn1137.63 (8)C23—C18—C19—C202.2 (3)
N1—Mn2—O5—Mn1150.64 (7)C17—C18—C19—C142.8 (3)
O8ii—Mn2—N1—C25176.3 (3)C23—C18—C19—C14175.6 (2)
O2—Mn2—N1—C257.4 (2)C14—C19—C20—C21177.6 (2)
O3iii—Mn2—N1—C2580.76 (19)C18—C19—C20—C210.0 (3)
O5—Mn2—N1—C2598.1 (2)C19—C20—C21—C222.0 (4)
N2—Mn2—N1—C25179.9 (2)C20—C21—C22—C231.9 (4)
O8ii—Mn2—N1—C290.9 (4)C21—C22—C23—C180.3 (4)
O2—Mn2—N1—C29175.46 (16)C17—C18—C23—C22179.4 (2)
O3iii—Mn2—N1—C2996.40 (16)C19—C18—C23—C222.3 (3)
O5—Mn2—N1—C2984.77 (16)Mn1vi—O7—C24—O818.2 (3)
N2—Mn2—N1—C292.70 (15)Mn1vi—O7—C24—C17161.82 (17)
O8ii—Mn2—N2—C364.72 (19)Mn2vi—O8—C24—O745.2 (4)
O2—Mn2—N2—C36148.4 (2)Mn2vi—O8—C24—C17134.8 (2)
O3iii—Mn2—N2—C36100.44 (18)C16—C17—C24—O764.1 (3)
O5—Mn2—N2—C3677.79 (18)C18—C17—C24—O7120.7 (3)
N1—Mn2—N2—C36176.2 (2)C16—C17—C24—O8115.9 (3)
O8ii—Mn2—N2—C33177.08 (15)C18—C17—C24—O859.3 (3)
O2—Mn2—N2—C3329.8 (3)C29—N1—C25—C260.8 (4)
O3iii—Mn2—N2—C3381.36 (15)Mn2—N1—C25—C26177.9 (2)
O5—Mn2—N2—C33100.41 (15)N1—C25—C26—C270.9 (4)
N1—Mn2—N2—C331.99 (14)C25—C26—C27—C280.1 (5)
Mn1—O1—C1—O216.1 (4)C26—C27—C28—C291.2 (4)
Mn1—O1—C1—C2163.06 (14)C26—C27—C28—C30178.7 (3)
Mn2—O2—C1—O17.0 (4)C25—N1—C29—C280.4 (3)
Mn2—O2—C1—C2172.07 (16)Mn2—N1—C29—C28177.00 (17)
O1—C1—C2—C356.6 (3)C25—N1—C29—C33179.6 (2)
O2—C1—C2—C3124.2 (2)Mn2—N1—C29—C333.1 (2)
O1—C1—C2—C7118.8 (2)C27—C28—C29—N11.3 (4)
O2—C1—C2—C760.4 (3)C30—C28—C29—N1178.5 (2)
C7—C2—C3—C41.2 (3)C27—C28—C29—C33178.6 (2)
C1—C2—C3—C4176.65 (19)C30—C28—C29—C331.6 (4)
C2—C3—C4—C51.8 (3)C27—C28—C30—O96.6 (5)
C3—C4—C5—C62.5 (3)C29—C28—C30—O9173.2 (3)
C3—C4—C5—C12179.48 (19)C27—C28—C30—C31174.9 (3)
C4—C5—C6—C70.3 (3)C29—C28—C30—C315.2 (4)
C12—C5—C6—C7178.25 (19)O9—C30—C31—O105.6 (5)
C4—C5—C6—C11175.6 (2)C28—C30—C31—O10175.9 (3)
C12—C5—C6—C112.4 (3)O9—C30—C31—C32173.1 (3)
C11—C6—C7—C2178.6 (2)C28—C30—C31—C325.4 (4)
C5—C6—C7—C22.6 (3)O10—C31—C32—C341.0 (4)
C11—C6—C7—C82.4 (3)C30—C31—C32—C34177.7 (3)
C5—C6—C7—C8173.62 (19)O10—C31—C32—C33179.5 (3)
C3—C2—C7—C63.4 (3)C30—C31—C32—C331.9 (4)
C1—C2—C7—C6178.75 (19)C36—N2—C33—C321.9 (3)
C3—C2—C7—C8172.7 (2)Mn2—N2—C33—C32179.80 (17)
C1—C2—C7—C82.6 (3)C36—N2—C33—C29177.2 (2)
C6—C7—C8—C90.7 (3)Mn2—N2—C33—C291.2 (2)
C2—C7—C8—C9176.8 (2)C34—C32—C33—N20.5 (3)
C7—C8—C9—C101.3 (4)C31—C32—C33—N2179.1 (2)
C8—C9—C10—C111.6 (4)C34—C32—C33—C29178.5 (2)
C9—C10—C11—C60.1 (4)C31—C32—C33—C291.9 (3)
C7—C6—C11—C102.2 (4)N1—C29—C33—N21.3 (3)
C5—C6—C11—C10173.7 (2)C28—C29—C33—N2178.8 (2)
Mn1v—O4—C12—O32.2 (4)N1—C29—C33—C32177.8 (2)
Mn1v—O4—C12—C5175.79 (15)C28—C29—C33—C322.2 (3)
Mn2iv—O3—C12—O4139.82 (19)C33—C32—C34—C351.4 (4)
Mn2iv—O3—C12—C542.2 (3)C31—C32—C34—C35179.0 (2)
C4—C5—C12—O4130.1 (2)C32—C34—C35—C361.8 (4)
C6—C5—C12—O451.9 (3)C33—N2—C36—C351.4 (3)
C4—C5—C12—O348.0 (3)Mn2—N2—C36—C35179.60 (18)
C6—C5—C12—O3130.0 (2)C34—C35—C36—N20.4 (4)
Symmetry codes: (i) x+1, y+3/2, z+1/2; (ii) x+1, y+1/2, z+3/2; (iii) x, y+3/2, z+1/2; (iv) x, y+3/2, z1/2; (v) x1, y+3/2, z1/2; (vi) x+1, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O3i0.85 (1)1.93 (2)2.720 (2)155 (3)
Symmetry code: (i) x+1, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]
Mr766.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.4393 (8), 19.2477 (18), 19.2504 (19)
β (°) 101.781 (1)
V3)3061.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.27 × 0.26 × 0.20
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.794, 0.841
No. of measured, independent and
observed [I > 2σ(I)] reflections
16986, 6015, 4853
Rint0.025
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.096, 1.03
No. of reflections6015
No. of parameters466
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
Mn1—O12.106 (2)Mn2—O22.125 (2)
Mn1—O4i2.137 (2)Mn2—O3iii2.173 (2)
Mn1—O52.190 (2)Mn2—O52.192 (2)
Mn1—O62.545 (2)Mn2—O8ii2.104 (2)
Mn1—O7ii2.182 (2)Mn2—N12.273 (2)
Mn1—O1W2.157 (2)Mn2—N22.268 (2)
Symmetry codes: (i) x+1, y+3/2, z+1/2; (ii) x+1, y+1/2, z+3/2; (iii) x, y+3/2, z+1/2.
 

Acknowledgements

The authors thank Tianjin Agricultural University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBoeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m421.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, H.-D., Li, X.-Y., Xu, M.-L. & Ng, S. W. (2008). Acta Cryst. E64, m701–m702.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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