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The reaction of manganese(II) nitrate with the proton-transfer compound piperazinediium pyridine-2,6-dicarboxyl­ate, or (pipzH2)(pydc), in aqueous solution leads to the formation of the title compound, (C4H12N2)[Mn(C7H3NO4)2]·6H2O. The anion is a six-coordinate complex with a distorted octa­hedral geometry around the central atom. In the crystal structure, intra- and inter­molecular O—H...O and N—H...O hydrogen bonds connect the various components into a supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032521/hk2106sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032521/hk2106Isup2.hkl
Contains datablock I

CCDC reference: 621368

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.131
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

Piperazinediium bis(pyridine-2,6-dicarboxylato)manganate(II) hexahydrate top
Crystal data top
(C4H12N2)[Mn(C7H3NO4)2]·6H2OF(000) = 1212
Mr = 581.40Dx = 1.523 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 17671 reflections
a = 13.553 (3) Åθ = 2.5–27.6°
b = 8.4219 (19) ŵ = 0.60 mm1
c = 22.215 (5) ÅT = 150 K
V = 2535.7 (10) Å3Block, yellow
Z = 40.36 × 0.35 × 0.25 mm
Data collection top
Bruker SMART 1000
diffractometer
2902 independent reflections
Radiation source: fine-focus sealed tube2003 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 100 pixels mm-1θmax = 27.5°, θmin = 1.8°
ω scansh = 1717
Absorption correction: multi-scan
SADABS (Sheldrick, 1998)
k = 1010
Tmin = 0.814, Tmax = 0.865l = 2828
20178 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0874P)2 + 0.3048P]
where P = (Fo2 + 2Fc2)/3
2902 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.34 e Å3
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
Mn10.50000.78378 (6)0.25000.03363 (17)
N10.34181 (13)0.7985 (2)0.23799 (7)0.0294 (4)
N20.51209 (13)1.1300 (2)0.04065 (8)0.0332 (4)
H2B0.46001.10410.06750.040*
H2A0.54061.22750.05330.040*
O10.42991 (12)0.61671 (19)0.31635 (7)0.0435 (4)
O20.28808 (14)0.5661 (2)0.36452 (8)0.0519 (5)
O30.35595 (12)1.04607 (19)0.11112 (7)0.0413 (4)
O40.47074 (12)0.95117 (19)0.17335 (7)0.0417 (4)
O50.00940 (14)0.9460 (2)0.08147 (11)0.0610 (6)
H5A0.01410.99750.11670.073*
H5B0.06631.00640.07150.073*
O60.17616 (14)1.1367 (3)0.05585 (9)0.0793 (7)
H6A0.23691.10430.07330.095*
H6B0.19771.15460.01570.095*
O70.19740 (13)0.80028 (19)0.43455 (7)0.0473 (4)
H7A0.22430.72160.40870.057*
H7B0.18990.88990.40900.057*
C10.33795 (18)0.6271 (3)0.32298 (10)0.0377 (5)
C20.28219 (16)0.7209 (2)0.27593 (10)0.0319 (5)
C30.18050 (17)0.7283 (3)0.27005 (11)0.0384 (5)
H30.13850.67510.29770.046*
C40.14187 (18)0.8151 (3)0.22290 (11)0.0417 (6)
H40.07240.82080.21740.050*
C50.20429 (17)0.8937 (3)0.18360 (10)0.0393 (5)
H50.17840.95280.15080.047*
C60.30487 (16)0.8847 (2)0.19298 (9)0.0303 (5)
C70.38326 (16)0.9668 (2)0.15584 (9)0.0329 (5)
C80.46699 (18)1.1547 (3)0.01973 (10)0.0374 (5)
H8A0.51881.18480.04900.045*
H8B0.41831.24210.01770.045*
C90.58337 (16)0.9960 (3)0.04024 (11)0.0381 (5)
H9A0.61060.98070.08120.046*
H9B0.63881.02100.01280.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0273 (3)0.0402 (3)0.0334 (3)0.0000.00125 (19)0.000
N10.0303 (10)0.0305 (9)0.0275 (9)0.0008 (7)0.0021 (7)0.0003 (7)
N20.0351 (10)0.0305 (9)0.0339 (10)0.0065 (8)0.0034 (7)0.0029 (8)
O10.0394 (10)0.0479 (10)0.0431 (9)0.0008 (7)0.0011 (7)0.0122 (8)
O20.0592 (11)0.0478 (10)0.0488 (10)0.0092 (9)0.0190 (9)0.0197 (8)
O30.0397 (9)0.0508 (10)0.0335 (8)0.0036 (8)0.0030 (7)0.0128 (7)
O40.0310 (8)0.0521 (10)0.0418 (9)0.0029 (7)0.0012 (7)0.0131 (8)
O50.0584 (12)0.0507 (11)0.0738 (13)0.0105 (9)0.0143 (10)0.0217 (10)
O60.0445 (11)0.130 (2)0.0633 (13)0.0084 (12)0.0049 (10)0.0358 (13)
O70.0601 (11)0.0390 (9)0.0429 (10)0.0028 (8)0.0089 (8)0.0058 (7)
C10.0458 (14)0.0316 (12)0.0359 (12)0.0019 (10)0.0037 (10)0.0019 (9)
C20.0367 (12)0.0297 (11)0.0293 (11)0.0009 (9)0.0043 (9)0.0018 (9)
C30.0357 (13)0.0422 (13)0.0372 (12)0.0066 (10)0.0084 (10)0.0010 (10)
C40.0286 (12)0.0554 (15)0.0412 (13)0.0007 (11)0.0013 (10)0.0037 (11)
C50.0350 (12)0.0493 (13)0.0336 (12)0.0027 (10)0.0032 (9)0.0025 (10)
C60.0315 (11)0.0328 (11)0.0265 (10)0.0006 (9)0.0005 (9)0.0014 (8)
C70.0337 (12)0.0350 (12)0.0299 (11)0.0003 (9)0.0028 (9)0.0000 (9)
C80.0419 (12)0.0330 (11)0.0373 (12)0.0007 (10)0.0002 (10)0.0015 (10)
C90.0337 (12)0.0422 (13)0.0383 (12)0.0011 (10)0.0012 (9)0.0026 (10)
Geometric parameters (Å, º) top
Mn1—N12.1640 (19)O6—H6B0.9499
Mn1—N1i2.1640 (19)O7—H7A0.9499
Mn1—O4i2.2458 (16)O7—H7B0.9500
Mn1—O42.2458 (16)C1—C21.513 (3)
Mn1—O1i2.2484 (16)C2—C31.386 (3)
Mn1—O12.2484 (16)C3—C41.380 (4)
N1—C61.333 (3)C3—H30.9500
N1—C21.338 (3)C4—C51.384 (3)
N2—C91.486 (3)C4—H40.9500
N2—C81.489 (3)C5—C61.381 (3)
N2—H2B0.9500C5—H50.9500
N2—H2A0.9500C6—C71.512 (3)
O1—C11.258 (3)C8—C9ii1.511 (3)
O2—C11.254 (3)C8—H8A0.9900
O3—C71.253 (3)C8—H8B0.9900
O4—C71.255 (3)C9—C8ii1.511 (3)
O5—H5A0.9501C9—H9A0.9900
O5—H5B0.9500C9—H9B0.9900
O6—H6A0.9500
N1—Mn1—N1i173.44 (9)O1—C1—C2116.77 (19)
N1—Mn1—O4i103.44 (6)N1—C2—C3121.3 (2)
N1i—Mn1—O4i72.28 (6)N1—C2—C1112.87 (19)
N1—Mn1—O472.28 (6)C3—C2—C1125.8 (2)
N1i—Mn1—O4103.44 (6)C4—C3—C2118.2 (2)
O4i—Mn1—O4102.24 (9)C4—C3—H3120.9
N1—Mn1—O1i111.94 (6)C2—C3—H3120.9
N1i—Mn1—O1i72.43 (6)C3—C4—C5120.0 (2)
O4i—Mn1—O1i144.61 (6)C3—C4—H4120.0
O4—Mn1—O1i88.30 (6)C5—C4—H4120.0
N1—Mn1—O172.42 (6)C6—C5—C4118.8 (2)
N1i—Mn1—O1111.94 (6)C6—C5—H5120.6
O4i—Mn1—O188.30 (6)C4—C5—H5120.6
O4—Mn1—O1144.61 (6)N1—C6—C5120.9 (2)
O1i—Mn1—O1102.52 (9)N1—C6—C7113.22 (18)
C6—N1—C2120.77 (19)C5—C6—C7125.86 (19)
C6—N1—Mn1119.71 (14)O3—C7—O4125.5 (2)
C2—N1—Mn1119.52 (14)O3—C7—C6117.95 (19)
C9—N2—C8111.55 (18)O4—C7—C6116.54 (18)
C9—N2—H2B108.2N2—C8—C9ii109.87 (19)
C8—N2—H2B107.1N2—C8—H8A109.7
C9—N2—H2A113.2C9ii—C8—H8A109.7
C8—N2—H2A108.3N2—C8—H8B109.7
H2B—N2—H2A108.3C9ii—C8—H8B109.7
C1—O1—Mn1116.87 (14)H8A—C8—H8B108.2
C7—O4—Mn1117.88 (14)N2—C9—C8ii110.25 (18)
H5A—O5—H5B102.6N2—C9—H9A109.6
H6A—O6—H6B99.3C8ii—C9—H9A109.6
H7A—O7—H7B103.5N2—C9—H9B109.6
O2—C1—O1126.3 (2)C8ii—C9—H9B109.6
O2—C1—C2116.9 (2)H9A—C9—H9B108.1
O4i—Mn1—N1—C6102.17 (15)Mn1—N1—C2—C11.3 (2)
O4—Mn1—N1—C63.40 (15)O2—C1—C2—N1171.8 (2)
O1i—Mn1—N1—C677.27 (16)O1—C1—C2—N18.7 (3)
O1—Mn1—N1—C6174.01 (16)O2—C1—C2—C39.0 (3)
O4i—Mn1—N1—C277.80 (16)O1—C1—C2—C3170.4 (2)
O4—Mn1—N1—C2176.57 (16)N1—C2—C3—C41.6 (3)
O1i—Mn1—N1—C2102.77 (16)C1—C2—C3—C4177.5 (2)
O1—Mn1—N1—C26.02 (15)C2—C3—C4—C51.0 (4)
N1—Mn1—O1—C111.07 (16)C3—C4—C5—C60.7 (4)
N1i—Mn1—O1—C1163.72 (16)C2—N1—C6—C51.3 (3)
O1i—Mn1—O1—C1120.40 (18)Mn1—N1—C6—C5178.78 (16)
O4i—Mn1—O1—C193.61 (17)C2—N1—C6—C7178.59 (18)
O1i—Mn1—O4—C7108.16 (16)Mn1—N1—C6—C71.4 (2)
O4i—Mn1—O4—C7105.93 (17)C4—C5—C6—N11.8 (3)
O4—Mn1—O1—C115.3 (2)C4—C5—C6—C7178.0 (2)
N1—Mn1—O4—C75.53 (16)Mn1—O4—C7—O3174.50 (16)
N1i—Mn1—O4—C7179.64 (15)Mn1—O4—C7—C66.7 (2)
O1—Mn1—O4—C71.3 (2)N1—C6—C7—O3177.47 (18)
Mn1—O1—C1—O2166.47 (19)C5—C6—C7—O32.7 (3)
Mn1—O1—C1—C214.1 (3)N1—C6—C7—O43.6 (3)
C6—N1—C2—C30.5 (3)C5—C6—C7—O4176.2 (2)
Mn1—N1—C2—C3179.50 (16)C9—N2—C8—C9ii57.4 (2)
C6—N1—C2—C1178.69 (18)C8—N2—C9—C8ii57.6 (3)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O30.951.782.725 (2)174
N2—H2A···O5iii0.952.062.826 (3)137
N2—H2A···O7iv0.952.232.944 (2)131
O5—H5A···O1v0.951.952.895 (3)174
O5—H5B···O60.951.882.830 (3)176
O6—H6A···O30.951.882.833 (3)177
O6—H6B···O7vi0.951.842.761 (3)162
O7—H7A···O20.951.852.797 (2)174
O7—H7B···O2iii0.951.812.733 (2)164
Symmetry codes: (iii) x+1/2, y+1/2, z; (iv) x+1/2, y+1/2, z+1/2; (v) x1/2, y+1/2, z+1/2; (vi) x, y+2, z1/2.
 

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