metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Aqua­(4-nitro­phthalato-κO1)bis­­[2-(1H-pyrazol-3-yl-κN2)pyridine-κN]­mangan­ese(II) hemihydrate

aCollege of Chemistry and Biology, Beihua University, Jilin 132013, People's Republic of China
*Correspondence e-mail: nilei_bh@163.com

(Received 28 August 2010; accepted 8 November 2010; online 13 November 2010)

In the title compound, [Mn(C8H3NO6)(C8H7N3)2(H2O)]·0.5H2O, the Mn2+ ion is octa­hedrally coordinated by two 2-(1H-pyrazol-3-yl)pyridine ligands, one 4-nitro­phthalate ligand and one coordinated water mol­ecule leading to an overall MnN4O2 coordination environment. The two 2-(1H-pyrazol-3-yl)pyridine ligands, which deviate from planarity by 0.0187 (2) and 0.0601 (2) Å, make a dihedral angle of 81.90 (6)°. An intra­molecular N—H⋯O hydrogen bond occurs. Inter­molecular ππ stacking inter­actions with a face-to-face separation of 3.61 (1) Å between the 2-(1H-pyrazol-3-yl)pyridine ligands is observed. Additionally, O—H⋯O hydrogen bonding involving the uncoordinated water (which is situated on an inversion center), coordinated water mol­ecules and 2-(1H-pyrazol-3-yl)pyridine ligands leads to a three-dimensional network in the crystal structure.

Related literature

For the use of 4-nitro-phthalic acid for metal-organic frameworks, see: Xu et al. (2009[Xu, B.-Y., Xie, T., Lu, S.-J., Xue, B. & Li, W. (2009). Acta Cryst. E65, m856-m857.]); Guo & Guo (2007[Guo, M.-L. & Guo, C.-H. (2007). Acta Cryst. C63, m595-m597.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C8H3NO6)(C8H7N3)2(H2O)]·0.5H2O

  • Mr = 581.41

  • Triclinic, [P \overline 1]

  • a = 10.5996 (7) Å

  • b = 11.2654 (7) Å

  • c = 11.9493 (7) Å

  • α = 96.275 (2)°

  • β = 112.485 (2)°

  • γ = 96.902 (2)°

  • V = 1289.94 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.57 mm−1

  • T = 294 K

  • 0.12 × 0.10 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.956

  • 13775 measured reflections

  • 4492 independent reflections

  • 4112 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.00

  • 4492 reflections

  • 364 parameters

  • 3 restraints

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

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H2W⋯O4i 0.82 (2) 1.80 (2) 2.615 (2) 171 (3)
N1—H1A⋯O1 0.86 1.86 2.644 (3) 152
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The synthesis of metal-organic frameworks (MOFs) has attracted continuous research interest not only because of their appealing structural and topological novelty, but also due to their unusual optical, electronic, magnetic, and catalytic properties, as well as their potential medical application (Xu et al. (2009); Guo & Guo (2007)). Here, we describe the synthesis and structural characterization of the title compound.

Single crystal X-ray diffraction analysis revealed that the asymmetric unit of the title compound, [(Mn(C8H7N3)2(C8H3NO6)(H2O)] × 0.5 H2O, consists of one Mn2+ ion that is octahedrally coordinated by two 2-(1H-pyrazol-3-yl)-pyridine ligands, one 4-nitro-phthalato ligand and one coordinated water molecule leading to an overall MnN4O2 coordination environment (Figure 1). Deviations of the two 2-(1H-pyrazol-3-yl)-pyridine moieties from planarity are 0.0187 (2) and 0.0601 (2) Å, respectively. The dihedral angle between the two 3-(2-pyridyl)-1H-pyrazole planes is 81.90 (6)°. The Mn-N and Mn-O bond distances are in the range of 2.200 (2)—2.359 (2) and 2.126 (2)—2.162 (2) Å, respectively. Intermolecular π-π stacking interactions with a face-to-face separation of 3.61 (1) Å between the 2-(1H-pyrazol-3-yl)-pyridine ligands is observed. Additionally, extensive hydrogen bonding involving solvent water (which are situated at a crystallographic center of inversion), coordinated water molecules and 2-(1H-pyrazol-3-yl)-pyridine ligands leads to a three dimensional network in the crystal structure (Figure 2).

Related literature top

For the use of 4-nitro-phthalic acid for metal-organic frameworks, see: Xu et al. (2009); Guo & Guo (2007).

Experimental top

A mixture of manganese sulfate hydrate (0.33 mmol, 0.050 g), 2-(1H-pyrazol-3-yl)-pyridine (0.32 mmoL, 0.05 g), and 4-nitrophthalic acid (0.24 mmoL, 0.05 g), gadolinium(III) nitrate pentahydrate (0.12 mmoL, 0.05 g), and 14 ml H2O was sealed in a 25 ml Teflon-lined stainless steel autoclave at 433 K for three days. Pink crystals suitable for the X-ray experiment were obtained after cooling down to room temperature (yield: 76%). Anal. Calc. for C48H40Mn2N14O15: C 49.53, H 3.44, N 16.85%; Found: C 49.36, H 3.32, N 16.72%.

Refinement top

All hydrogen atoms bound to carbon were refined using a riding model with C—H = 0.93 Å and Uiso = 1.2Ueq (C). The H atoms of the coordinated water molecule were located from difference density maps and were refined with d(O—H) = 0.83 (2) Å, and with a fixed Uiso of 0.80 Å2. Refinement of the H atoms of lattice water did not result in a reasonable model since there is only 0.5 water situated at a crystallographic center of inversion. Hydrogen positions would therefore have to be split. Hence corresponding hydrogen positions were excluded from the final refinement.

Structure description top

The synthesis of metal-organic frameworks (MOFs) has attracted continuous research interest not only because of their appealing structural and topological novelty, but also due to their unusual optical, electronic, magnetic, and catalytic properties, as well as their potential medical application (Xu et al. (2009); Guo & Guo (2007)). Here, we describe the synthesis and structural characterization of the title compound.

Single crystal X-ray diffraction analysis revealed that the asymmetric unit of the title compound, [(Mn(C8H7N3)2(C8H3NO6)(H2O)] × 0.5 H2O, consists of one Mn2+ ion that is octahedrally coordinated by two 2-(1H-pyrazol-3-yl)-pyridine ligands, one 4-nitro-phthalato ligand and one coordinated water molecule leading to an overall MnN4O2 coordination environment (Figure 1). Deviations of the two 2-(1H-pyrazol-3-yl)-pyridine moieties from planarity are 0.0187 (2) and 0.0601 (2) Å, respectively. The dihedral angle between the two 3-(2-pyridyl)-1H-pyrazole planes is 81.90 (6)°. The Mn-N and Mn-O bond distances are in the range of 2.200 (2)—2.359 (2) and 2.126 (2)—2.162 (2) Å, respectively. Intermolecular π-π stacking interactions with a face-to-face separation of 3.61 (1) Å between the 2-(1H-pyrazol-3-yl)-pyridine ligands is observed. Additionally, extensive hydrogen bonding involving solvent water (which are situated at a crystallographic center of inversion), coordinated water molecules and 2-(1H-pyrazol-3-yl)-pyridine ligands leads to a three dimensional network in the crystal structure (Figure 2).

For the use of 4-nitro-phthalic acid for metal-organic frameworks, see: Xu et al. (2009); Guo & Guo (2007).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound, displayed with hydrogen bonds as dashed lines.
Aqua(4-nitrophthalato-κO1)bis[2-(1H-pyrazol-3-yl- κN2)pyridine-κN]manganese(II) hemihydrate top
Crystal data top
[Mn(C8H3NO6)(C8H7N3)2(H2O)]·0.5H2OZ = 2
Mr = 581.41F(000) = 594
Triclinic, P1Dx = 1.497 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5996 (7) ÅCell parameters from 4492 reflections
b = 11.2654 (7) Åθ = 1.9–25.0°
c = 11.9493 (7) ŵ = 0.57 mm1
α = 96.275 (2)°T = 294 K
β = 112.485 (2)°Block, pink
γ = 96.902 (2)°0.12 × 0.10 × 0.08 mm
V = 1289.94 (14) Å3
Data collection top
Bruker APEXII CCD
diffractometer
4492 independent reflections
Radiation source: fine-focus sealed tube4112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1212
Tmin = 0.935, Tmax = 0.956k = 1312
13775 measured reflectionsl = 1414
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.065P)2 + 0.6953P]
where P = (Fo2 + 2Fc2)/3
4492 reflections(Δ/σ)max = 0.001
364 parametersΔρmax = 0.67 e Å3
3 restraintsΔρmin = 0.56 e Å3
Crystal data top
[Mn(C8H3NO6)(C8H7N3)2(H2O)]·0.5H2Oγ = 96.902 (2)°
Mr = 581.41V = 1289.94 (14) Å3
Triclinic, P1Z = 2
a = 10.5996 (7) ÅMo Kα radiation
b = 11.2654 (7) ŵ = 0.57 mm1
c = 11.9493 (7) ÅT = 294 K
α = 96.275 (2)°0.12 × 0.10 × 0.08 mm
β = 112.485 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
4492 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4112 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.956Rint = 0.016
13775 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.67 e Å3
4492 reflectionsΔρmin = 0.56 e Å3
364 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
xyzUiso*/Ueq
C10.7173 (4)0.2731 (3)0.9226 (3)0.0712 (8)
H10.63430.25680.93230.085*
C20.8448 (4)0.3131 (3)1.0143 (3)0.0697 (8)
H20.86680.32941.09830.084*
C30.9359 (3)0.3247 (2)0.9554 (2)0.0518 (6)
C41.0853 (3)0.3638 (2)1.0005 (2)0.0537 (6)
C51.1703 (4)0.4045 (3)1.1239 (2)0.0695 (8)
H51.13280.40731.18280.083*
C61.3098 (4)0.4403 (3)1.1578 (3)0.0831 (10)
H61.36800.46731.24010.100*
C71.3632 (4)0.4362 (3)1.0692 (3)0.0802 (9)
H71.45760.46071.09030.096*
C81.2730 (3)0.3948 (3)0.9483 (3)0.0670 (7)
H81.30900.39160.88840.080*
C91.3004 (3)0.2422 (3)0.5695 (3)0.0635 (7)
H91.36740.26620.54030.076*
C101.2660 (3)0.1287 (3)0.5905 (3)0.0611 (7)
H101.30370.06040.57860.073*
C111.1618 (2)0.13717 (19)0.63382 (19)0.0406 (4)
C121.0839 (2)0.04615 (18)0.67283 (18)0.0404 (4)
C131.0928 (3)0.0766 (2)0.6586 (2)0.0526 (6)
H131.14900.10490.62170.063*
C141.0177 (3)0.1549 (2)0.6995 (3)0.0663 (7)
H141.02180.23720.69060.080*
C150.9309 (3)0.0111 (2)0.7633 (3)0.0688 (8)
H150.87470.04050.79950.083*
C160.9367 (4)0.1107 (3)0.7536 (3)0.0761 (8)
H160.88610.16200.78340.091*
C170.6605 (2)0.2144 (2)0.5118 (2)0.0513 (6)
C180.5813 (2)0.1929 (2)0.3746 (2)0.0427 (5)
C190.4714 (3)0.0954 (2)0.3232 (2)0.0572 (6)
H190.44380.05230.37460.069*
C200.4030 (3)0.0616 (2)0.1979 (3)0.0619 (7)
H200.32940.00340.16390.074*
C210.4462 (2)0.1264 (2)0.1246 (2)0.0545 (6)
C220.5544 (2)0.2235 (2)0.1721 (2)0.0479 (5)
H220.58200.26480.11970.058*
C230.6216 (2)0.25915 (18)0.29779 (19)0.0400 (4)
C240.7320 (2)0.3719 (2)0.3445 (2)0.0462 (5)
Mn10.97367 (3)0.28597 (3)0.71009 (3)0.03701 (12)
N10.7320 (2)0.26121 (19)0.8159 (2)0.0564 (5)
H1A0.66500.23660.74500.068*
N20.8652 (2)0.29291 (17)0.83442 (17)0.0485 (4)
N31.1369 (2)0.35929 (18)0.91298 (18)0.0528 (5)
N41.22077 (19)0.31285 (17)0.59823 (18)0.0474 (4)
H41.22400.38840.59190.057*
N51.13476 (17)0.25018 (15)0.63847 (16)0.0393 (4)
N61.0021 (2)0.08928 (16)0.72337 (18)0.0467 (4)
N70.3749 (3)0.0899 (3)0.0097 (2)0.0805 (7)
O10.5935 (2)0.2119 (4)0.5746 (2)0.1504 (16)
O20.78795 (15)0.22449 (14)0.54996 (14)0.0475 (4)
O30.7370 (2)0.44475 (15)0.43391 (16)0.0596 (4)
O40.8061 (2)0.38723 (19)0.2870 (2)0.0791 (6)
O50.4122 (3)0.1463 (3)0.0749 (2)0.1086 (9)
O60.2814 (4)0.0044 (3)0.0487 (3)0.1654 (18)
O1W0.96188 (16)0.46463 (14)0.66095 (15)0.0479 (4)
O2W0.50000.50000.50000.208 (3)
H1W0.9011 (17)0.454 (3)0.5913 (10)0.080*
H2W1.0347 (14)0.507 (2)0.670 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.097 (2)0.0723 (18)0.0770 (19)0.0202 (16)0.0667 (19)0.0216 (15)
C20.109 (2)0.0717 (18)0.0557 (16)0.0283 (17)0.0556 (18)0.0216 (13)
C30.0855 (18)0.0398 (11)0.0455 (12)0.0208 (11)0.0388 (12)0.0118 (9)
C40.0838 (18)0.0380 (12)0.0446 (12)0.0213 (11)0.0277 (12)0.0100 (9)
C50.106 (2)0.0573 (16)0.0450 (14)0.0253 (15)0.0264 (15)0.0096 (12)
C60.104 (3)0.0694 (19)0.0505 (16)0.0196 (18)0.0035 (17)0.0064 (14)
C70.073 (2)0.076 (2)0.0705 (19)0.0113 (16)0.0083 (16)0.0066 (15)
C80.0655 (17)0.0692 (17)0.0592 (16)0.0113 (14)0.0192 (13)0.0037 (13)
C90.0590 (15)0.0756 (18)0.0797 (18)0.0222 (13)0.0481 (14)0.0230 (14)
C100.0679 (16)0.0625 (16)0.0775 (17)0.0340 (13)0.0465 (14)0.0217 (13)
C110.0430 (11)0.0413 (11)0.0400 (11)0.0145 (9)0.0174 (9)0.0070 (8)
C120.0442 (11)0.0390 (11)0.0347 (10)0.0117 (9)0.0112 (9)0.0057 (8)
C130.0630 (14)0.0435 (12)0.0492 (13)0.0197 (11)0.0175 (11)0.0072 (10)
C140.0842 (19)0.0372 (13)0.0728 (17)0.0156 (12)0.0235 (15)0.0146 (12)
C150.0821 (19)0.0506 (14)0.101 (2)0.0164 (13)0.0608 (17)0.0260 (14)
C160.092 (2)0.0478 (15)0.105 (2)0.0101 (14)0.0540 (19)0.0311 (15)
C170.0418 (12)0.0668 (15)0.0513 (13)0.0064 (10)0.0257 (10)0.0111 (11)
C180.0337 (10)0.0464 (12)0.0515 (12)0.0080 (9)0.0206 (9)0.0084 (9)
C190.0470 (13)0.0583 (14)0.0676 (16)0.0026 (11)0.0259 (12)0.0176 (12)
C200.0428 (13)0.0561 (15)0.0722 (17)0.0106 (11)0.0149 (12)0.0028 (12)
C210.0420 (12)0.0584 (14)0.0500 (13)0.0027 (10)0.0089 (10)0.0010 (11)
C220.0416 (11)0.0532 (13)0.0472 (12)0.0032 (10)0.0170 (10)0.0096 (10)
C230.0338 (10)0.0382 (11)0.0475 (11)0.0056 (8)0.0162 (9)0.0067 (9)
C240.0433 (11)0.0391 (11)0.0504 (12)0.0008 (9)0.0143 (10)0.0085 (10)
Mn10.0428 (2)0.03495 (19)0.03942 (19)0.00804 (13)0.02298 (15)0.00565 (13)
N10.0672 (13)0.0579 (12)0.0593 (12)0.0069 (10)0.0432 (11)0.0088 (9)
N20.0655 (12)0.0437 (10)0.0483 (11)0.0105 (9)0.0356 (10)0.0075 (8)
N30.0663 (13)0.0466 (11)0.0465 (11)0.0141 (9)0.0234 (10)0.0048 (8)
N40.0476 (10)0.0460 (10)0.0576 (11)0.0075 (8)0.0302 (9)0.0124 (8)
N50.0414 (9)0.0379 (9)0.0432 (9)0.0072 (7)0.0221 (8)0.0062 (7)
N60.0541 (11)0.0376 (9)0.0570 (11)0.0102 (8)0.0298 (9)0.0121 (8)
N70.0622 (15)0.0935 (19)0.0578 (15)0.0044 (14)0.0031 (12)0.0036 (14)
O10.0515 (13)0.342 (5)0.0589 (13)0.015 (2)0.0337 (11)0.016 (2)
O20.0402 (8)0.0541 (9)0.0470 (8)0.0068 (7)0.0177 (7)0.0041 (7)
O30.0743 (12)0.0413 (9)0.0559 (10)0.0013 (8)0.0228 (9)0.0036 (8)
O40.0715 (13)0.0731 (13)0.0920 (14)0.0272 (10)0.0501 (12)0.0099 (11)
O50.0866 (17)0.167 (3)0.0508 (12)0.0142 (17)0.0190 (12)0.0042 (14)
O60.160 (3)0.160 (3)0.0776 (18)0.088 (3)0.0201 (19)0.0018 (18)
O1W0.0464 (9)0.0414 (8)0.0532 (9)0.0005 (7)0.0182 (7)0.0109 (7)
O2W0.190 (6)0.278 (8)0.248 (8)0.101 (6)0.165 (6)0.066 (6)
Geometric parameters (Å, º) top
C1—N11.338 (3)C15—H150.9300
C1—C21.357 (5)C16—H160.9300
C1—H10.9300C17—O11.216 (3)
C2—C31.398 (4)C17—O21.235 (3)
C2—H20.9300C17—C181.504 (3)
C3—N21.332 (3)C18—C191.393 (3)
C3—C41.456 (4)C18—C231.398 (3)
C4—N31.352 (3)C19—C201.375 (4)
C4—C51.390 (4)C19—H190.9300
C5—C61.370 (5)C20—C211.370 (4)
C5—H50.9300C20—H200.9300
C6—C71.378 (5)C21—C221.378 (3)
C6—H60.9300C21—N71.473 (3)
C7—C81.382 (4)C22—C231.380 (3)
C7—H70.9300C22—H220.9300
C8—N31.334 (4)C23—C241.511 (3)
C8—H80.9300C24—O41.235 (3)
C9—N41.337 (3)C24—O31.253 (3)
C9—C101.364 (4)Mn1—O22.1255 (15)
C9—H90.9300Mn1—O1W2.1619 (15)
C10—C111.396 (3)Mn1—N22.1995 (17)
C10—H100.9300Mn1—N52.2401 (16)
C11—N51.338 (3)Mn1—N62.2861 (18)
C11—C121.465 (3)Mn1—N32.359 (2)
C12—N61.338 (3)N1—N21.339 (3)
C12—C131.393 (3)N1—H1A0.8600
C13—C141.370 (4)N4—N51.347 (2)
C13—H130.9300N4—H40.8600
C14—C161.364 (4)N7—O61.203 (4)
C14—H140.9300N7—O51.203 (4)
C15—N61.334 (3)O1W—H1W0.820 (12)
C15—C161.375 (4)O1W—H2W0.82 (2)
N1—C1—C2108.0 (3)C18—C19—H19119.5
N1—C1—H1126.0C21—C20—C19118.2 (2)
C2—C1—H1126.0C21—C20—H20120.9
C1—C2—C3105.2 (2)C19—C20—H20120.9
C1—C2—H2127.4C20—C21—C22122.3 (2)
C3—C2—H2127.4C20—C21—N7118.6 (2)
N2—C3—C2109.7 (3)C22—C21—N7119.0 (2)
N2—C3—C4117.4 (2)C21—C22—C23119.7 (2)
C2—C3—C4132.9 (2)C21—C22—H22120.2
N3—C4—C5121.6 (3)C23—C22—H22120.2
N3—C4—C3115.1 (2)C22—C23—C18119.03 (19)
C5—C4—C3123.3 (2)C22—C23—C24117.40 (19)
C6—C5—C4119.2 (3)C18—C23—C24123.52 (19)
C6—C5—H5120.4O4—C24—O3125.3 (2)
C4—C5—H5120.4O4—C24—C23116.6 (2)
C5—C6—C7119.5 (3)O3—C24—C23118.0 (2)
C5—C6—H6120.2O2—Mn1—O1W86.45 (6)
C7—C6—H6120.2O2—Mn1—N293.74 (7)
C6—C7—C8118.3 (3)O1W—Mn1—N299.70 (7)
C6—C7—H7120.9O2—Mn1—N5101.41 (6)
C8—C7—H7120.9O1W—Mn1—N595.17 (6)
N3—C8—C7123.3 (3)N2—Mn1—N5159.38 (7)
N3—C8—H8118.3O2—Mn1—N689.68 (7)
C7—C8—H8118.3O1W—Mn1—N6166.14 (7)
N4—C9—C10108.0 (2)N2—Mn1—N693.83 (7)
N4—C9—H9126.0N5—Mn1—N672.55 (6)
C10—C9—H9126.0O2—Mn1—N3164.44 (7)
C9—C10—C11105.0 (2)O1W—Mn1—N394.04 (7)
C9—C10—H10127.5N2—Mn1—N370.82 (8)
C11—C10—H10127.5N5—Mn1—N394.05 (7)
N5—C11—C10110.3 (2)N6—Mn1—N393.24 (7)
N5—C11—C12118.75 (18)C1—N1—N2110.7 (2)
C10—C11—C12131.0 (2)C1—N1—H1A124.6
N6—C12—C13121.9 (2)N2—N1—H1A124.6
N6—C12—C11115.00 (18)C3—N2—N1106.40 (18)
C13—C12—C11123.1 (2)C3—N2—Mn1120.74 (17)
C14—C13—C12119.1 (2)N1—N2—Mn1132.63 (15)
C14—C13—H13120.5C8—N3—C4118.0 (2)
C12—C13—H13120.5C8—N3—Mn1126.27 (17)
C16—C14—C13119.2 (2)C4—N3—Mn1115.70 (17)
C16—C14—H14120.4C9—N4—N5111.07 (19)
C13—C14—H14120.4C9—N4—H4124.5
N6—C15—C16123.2 (3)N5—N4—H4124.5
N6—C15—H15118.4C11—N5—N4105.65 (16)
C16—C15—H15118.4C11—N5—Mn1116.41 (13)
C14—C16—C15118.9 (3)N4—N5—Mn1137.92 (13)
C14—C16—H16120.6C15—N6—C12117.8 (2)
C15—C16—H16120.6C15—N6—Mn1125.06 (16)
O1—C17—O2125.8 (2)C12—N6—Mn1116.60 (14)
O1—C17—C18117.3 (2)O6—N7—O5123.3 (3)
O2—C17—C18116.67 (19)O6—N7—C21117.6 (3)
C19—C18—C23119.6 (2)O5—N7—C21119.1 (3)
C19—C18—C17117.4 (2)C17—O2—Mn1142.44 (15)
C23—C18—C17122.66 (19)Mn1—O1W—H1W106 (2)
C20—C19—C18121.1 (2)Mn1—O1W—H2W117 (2)
C20—C19—H19119.5H1W—O1W—H2W115 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···O4i0.82 (2)1.80 (2)2.615 (2)171 (3)
N1—H1A···O10.861.862.644 (3)152
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Mn(C8H3NO6)(C8H7N3)2(H2O)]·0.5H2O
Mr581.41
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)10.5996 (7), 11.2654 (7), 11.9493 (7)
α, β, γ (°)96.275 (2), 112.485 (2), 96.902 (2)
V3)1289.94 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.57
Crystal size (mm)0.12 × 0.10 × 0.08
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.935, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
13775, 4492, 4112
Rint0.016
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 1.00
No. of reflections4492
No. of parameters364
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.67, 0.56

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···O4i0.82 (2)1.80 (2)2.615 (2)171 (3)
N1—H1A···O10.861.862.644 (3)151.7
Symmetry code: (i) x+2, y+1, z+1.
 

Acknowledgements

The authors acknowledge financial support from the Science Foundation of Beihua University.

References

First citationBruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.  Google Scholar
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGuo, M.-L. & Guo, C.-H. (2007). Acta Cryst. C63, m595–m597.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXu, B.-Y., Xie, T., Lu, S.-J., Xue, B. & Li, W. (2009). Acta Cryst. E65, m856–m857.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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