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The Zr atom in the title compound, {(C5H11N2)[Zr(C2O4)3]}n, is chelated by four oxalate groups in a square-antiprismatic geometry. Bridging by one of the three oxalate groups in the asymmetric unit gives rises to a helical tris­(oxalato)­zirconate chain that propagates along the b axis of the unit cell. The dications surround the chains and are tightly hydrogen bonded to them, resulting in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003806/hb6152sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003806/hb6152Isup2.hkl
Contains datablock I

CCDC reference: 269576

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.019
  • wR factor = 0.054
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C6 ... 1.54 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[N-methylpiperazinium(2+) [[bis(oxalato-κ2-O,O')zirconate(IV)]-µ2-oxalato-κ4O,O':O'',O''']] top
Crystal data top
(C5H11N2)[Zr(C2O4)3]F(000) = 920
Mr = 457.46Dx = 2.098 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5754 reflections
a = 9.5936 (5) Åθ = 2.4–28.5°
b = 11.3569 (5) ŵ = 0.84 mm1
c = 13.9792 (7) ÅT = 295 K
β = 108.023 (1)°Prism, colorless
V = 1448.4 (1) Å30.38 × 0.29 × 0.20 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
3273 independent reflections
Radiation source: fine-focus sealed tube3114 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1212
Tmin = 0.712, Tmax = 0.850k = 1414
15328 measured reflectionsl = 1817
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)] = 0.019Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.054H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.033P)2 + 0.4993P]
where P = (Fo2 + 2Fc2)/3
3273 reflections(Δ/σ)max = 0.001
247 parametersΔρmax = 0.32 e Å3
3 restraintsΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zr10.40531 (1)0.61472 (1)0.23939 (1)0.01225 (6)
O10.6077 (1)0.4936 (1)0.2636 (1)0.0186 (2)
O20.6764 (1)0.3025 (1)0.2752 (1)0.0180 (2)
O30.3347 (1)0.4277 (1)0.2314 (1)0.0186 (2)
O40.4056 (1)0.2390 (1)0.2481 (1)0.0177 (2)
O50.2496 (1)0.6116 (1)0.3232 (1)0.0192 (2)
O60.2142 (1)0.6073 (1)0.4741 (1)0.0330 (3)
O70.5241 (1)0.6283 (1)0.3955 (1)0.0221 (2)
O80.5242 (1)0.6361 (1)0.5547 (1)0.0266 (2)
O90.1869 (1)0.6149 (1)0.1280 (1)0.0210 (2)
O100.0619 (1)0.6209 (1)0.0358 (1)0.0337 (3)
O110.4349 (1)0.6068 (1)0.0951 (1)0.0221 (2)
O120.3312 (2)0.6238 (1)0.0715 (1)0.0340 (3)
N10.8003 (1)0.7599 (1)0.5989 (1)0.0249 (3)
N21.0445 (1)0.6961 (1)0.7717 (1)0.0266 (3)
C10.5861 (1)0.3860 (1)0.2638 (1)0.0149 (3)
C20.4290 (1)0.3470 (1)0.2471 (1)0.0150 (2)
C30.2933 (2)0.6142 (1)0.4214 (1)0.0196 (3)
C40.4613 (2)0.6275 (1)0.4648 (1)0.0187 (3)
C50.1762 (2)0.6175 (1)0.0343 (1)0.0214 (3)
C60.3253 (2)0.6163 (1)0.0135 (1)0.0213 (3)
C70.9129 (2)0.6723 (1)0.5911 (1)0.0286 (3)
C80.9829 (2)0.6096 (1)0.6899 (1)0.0301 (4)
C90.9313 (2)0.7801 (2)0.7814 (1)0.0279 (3)
C100.8637 (2)0.8440 (1)0.6834 (1)0.0260 (3)
C110.7405 (2)0.8263 (2)0.5022 (1)0.0348 (4)
H110.731 (2)0.719 (2)0.607 (1)0.035 (5)*
H211.112 (2)0.737 (2)0.759 (1)0.035 (5)*
H221.075 (2)0.662 (2)0.829 (1)0.048 (6)*
H7a0.98830.71250.57070.034*
H7b0.86710.61470.53980.034*
H8a0.91020.56130.70650.036*
H8b1.06040.55830.68350.036*
H9a0.97550.83660.83410.034*
H9b0.85580.73780.80010.034*
H10a0.78710.89610.69010.031*
H10b0.93780.89190.66810.031*
H11a0.69960.77180.44830.052*
H11b0.81800.87000.48880.052*
H11c0.66560.87960.50760.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zr10.01299 (8)0.01007 (8)0.01343 (8)0.00006 (4)0.00371 (5)0.00019 (4)
O10.0182 (5)0.0121 (5)0.0257 (5)0.0010 (3)0.0072 (4)0.0002 (3)
O20.0170 (4)0.0125 (4)0.0254 (5)0.0008 (3)0.0080 (4)0.0002 (4)
O30.0157 (4)0.0121 (4)0.0270 (5)0.0007 (3)0.0053 (4)0.0005 (4)
O40.0167 (5)0.0113 (5)0.0250 (5)0.0007 (3)0.0063 (4)0.0006 (3)
O50.0181 (5)0.0217 (5)0.0179 (5)0.0013 (4)0.0055 (4)0.0016 (3)
O60.0306 (6)0.0469 (7)0.0269 (6)0.0023 (5)0.0168 (5)0.0001 (5)
O70.0185 (5)0.0306 (5)0.0165 (5)0.0007 (4)0.0045 (4)0.0009 (4)
O80.0305 (6)0.0311 (5)0.0163 (5)0.0037 (5)0.0044 (4)0.0005 (4)
O90.0179 (5)0.0241 (5)0.0189 (5)0.0001 (4)0.0026 (4)0.0007 (4)
O100.0255 (6)0.0451 (7)0.0232 (6)0.0029 (5)0.0030 (5)0.0052 (5)
O110.0221 (5)0.0270 (5)0.0174 (5)0.0019 (4)0.0065 (4)0.0007 (4)
O120.0432 (7)0.0413 (7)0.0186 (5)0.0057 (5)0.0112 (5)0.0031 (4)
N10.0201 (6)0.0265 (6)0.0244 (6)0.0067 (5)0.0016 (5)0.0043 (5)
N20.0183 (6)0.0319 (7)0.0262 (7)0.0038 (5)0.0019 (5)0.0055 (5)
C10.0163 (7)0.0148 (7)0.0141 (6)0.0001 (4)0.0056 (5)0.0002 (4)
C20.0170 (6)0.0148 (6)0.0132 (6)0.0005 (5)0.0049 (5)0.0002 (5)
C30.0233 (7)0.0162 (6)0.0204 (7)0.0002 (5)0.0080 (6)0.0001 (5)
C40.0232 (7)0.0147 (6)0.0177 (6)0.0001 (5)0.0056 (5)0.0005 (5)
C50.0250 (7)0.0158 (7)0.0204 (7)0.0002 (5)0.0026 (6)0.0013 (5)
C60.0282 (8)0.0160 (7)0.0191 (7)0.0014 (5)0.0063 (6)0.0004 (5)
C70.0344 (8)0.0233 (7)0.0262 (7)0.0039 (6)0.0066 (6)0.0026 (6)
C80.0285 (8)0.0222 (8)0.0355 (9)0.0031 (6)0.0040 (7)0.0030 (6)
C90.0217 (7)0.0384 (9)0.0233 (7)0.0040 (6)0.0063 (6)0.0023 (6)
C100.0226 (7)0.0263 (7)0.0281 (7)0.0019 (6)0.0063 (6)0.0023 (6)
C110.0358 (9)0.0329 (9)0.0275 (8)0.0070 (7)0.0022 (7)0.0093 (7)
Geometric parameters (Å, º) top
Zr1—O12.318 (1)N1—C111.499 (2)
Zr1—O2i2.260 (1)N2—C91.483 (2)
Zr1—O32.222 (1)N2—C81.484 (2)
Zr1—O4i2.263 (1)C1—C21.517 (2)
Zr1—O52.165 (1)C3—C41.544 (2)
Zr1—O72.132 (1)C5—C61.545 (2)
Zr1—O92.190 (1)C7—C81.514 (2)
Zr1—O112.124 (1)C9—C101.509 (2)
O1—C11.240 (2)N1—H110.85 (1)
O2—C11.261 (2)N2—H210.86 (1)
O3—C21.258 (2)N2—H220.86 (1)
O4—C21.248 (2)C7—H7a0.97
O5—C31.306 (2)C7—H7b0.97
O6—C31.212 (2)C8—H8a0.97
O7—C41.289 (2)C8—H8b0.97
O8—C41.218 (2)C9—H9a0.97
O9—C51.281 (2)C9—H9b0.97
O10—C51.225 (2)C10—H10a0.97
O11—C61.295 (2)C10—H10b0.97
O12—C61.210 (2)C11—H11a0.96
N1—C101.494 (2)C11—H11b0.96
N1—C71.497 (2)C11—H11c0.96
O1—Zr1—O2i145.59 (3)O5—C3—C4111.8 (1)
O1—Zr1—O370.63 (3)O8—C4—O7125.3 (1)
O1—Zr1—O4i75.13 (4)O8—C4—C3122.4 (1)
O1—Zr1—O5126.76 (3)O7—C4—C3112.3 (1)
O1—Zr1—O774.66 (4)O10—C5—O9125.9 (2)
O1—Zr1—O9132.70 (3)O10—C5—C6120.1 (1)
O1—Zr1—O1176.18 (4)O9—C5—C6114.0 (1)
O2i—Zr1—O3143.72 (4)O12—C6—O11126.8 (2)
O2i—Zr1—O4i70.46 (3)O12—C6—C5120.8 (1)
O2i—Zr1—O577.67 (3)O11—C6—C5112.4 (1)
O2i—Zr1—O794.87 (4)N1—C7—C8111.9 (1)
O2i—Zr1—O972.92 (3)N2—C8—C7110.5 (1)
O2i—Zr1—O1195.67 (4)N2—C9—C10110.3 (1)
O3—Zr1—O4i145.59 (3)N1—C10—C9111.5 (1)
O3—Zr1—O576.15 (3)C10—N1—H11113 (1)
O3—Zr1—O7100.27 (4)C7—N1—H11105 (1)
O3—Zr1—O975.85 (3)C11—N1—H11107 (1)
O3—Zr1—O1192.30 (4)C9—N2—H21107 (1)
O4i—Zr1—O5129.76 (3)C8—N2—H21110 (1)
O4i—Zr1—O773.39 (4)C9—N2—H22105 (2)
O4i—Zr1—O9128.49 (3)C8—N2—H22111 (2)
O4i—Zr1—O1176.12 (4)H21—N2—H22112 (2)
O5—Zr1—O771.76 (4)N1—C7—H7a109.2
O5—Zr1—O973.52 (4)C8—C7—H7a109.2
O5—Zr1—O11146.14 (4)N1—C7—H7b109.2
O7—Zr1—O9144.93 (4)C8—C7—H7b109.2
O7—Zr1—O11142.09 (4)H7a—C7—H7b107.9
O9—Zr1—O1172.80 (4)N2—C8—H8a109.6
C1—O1—Zr1116.9 (1)C7—C8—H8a109.6
C1—O2—Zr1ii119.5 (1)N2—C8—H8b109.6
C2—O3—Zr1119.7 (1)C7—C8—H8b109.6
C2—O4—Zr1ii118.1 (1)H8a—C8—H8b108.1
C3—O5—Zr1121.2 (1)N2—C9—H9a109.6
C4—O7—Zr1122.9 (1)C10—C9—H9a109.6
C5—O9—Zr1118.9 (1)N2—C9—H9b109.6
C6—O11—Zr1121.5 (1)C10—C9—H9b109.6
C10—N1—C7110.8 (1)H9a—C9—H9b108.1
C10—N1—C11109.9 (1)N1—C10—H10a109.3
C7—N1—C11110.6 (1)C9—C10—H10a109.3
C9—N2—C8111.6 (1)N1—C10—H10b109.3
O1—C1—O2129.2 (1)C9—C10—H10b109.3
O1—C1—C2116.5 (1)H10a—C10—H10b108.0
O2—C1—C2114.3 (1)N1—C11—H11a109.5
O4—C2—O3126.5 (1)N1—C11—H11b109.5
O4—C2—C1117.3 (1)H11a—C11—H11b109.5
O3—C2—C1116.2 (1)N1—C11—H11c109.5
O6—C3—O5125.4 (1)H11a—C11—H11c109.5
O6—C3—C4122.8 (1)H11b—C11—H11c109.5
O11—Zr1—O1—C199.3 (1)O2i—Zr1—O11—C663.8 (1)
O7—Zr1—O1—C1105.2 (1)O4i—Zr1—O11—C6132.1 (1)
O5—Zr1—O1—C152.8 (1)O1—Zr1—O11—C6150.1 (1)
O9—Zr1—O1—C149.2 (1)Zr1—O1—C1—O2179.9 (1)
O3—Zr1—O1—C11.9 (1)Zr1—O1—C1—C20.6 (1)
O2i—Zr1—O1—C1179.0 (1)Zr1ii—O2—C1—O1175.8 (1)
O4i—Zr1—O1—C1178.4 (1)Zr1ii—O2—C1—C23.5 (1)
O11—Zr1—O3—C277.7 (1)Zr1ii—O4—C2—O3173.0 (1)
O7—Zr1—O3—C266.4 (1)Zr1ii—O4—C2—C15.4 (1)
O5—Zr1—O3—C2134.6 (1)Zr1—O3—C2—O4177.7 (1)
O9—Zr1—O3—C2149.3 (1)Zr1—O3—C2—C14.0 (2)
O2i—Zr1—O3—C2179.5 (1)O1—C1—C2—O4179.3 (1)
O4i—Zr1—O3—C29.1 (1)O2—C1—C2—O41.3 (2)
O1—Zr1—O3—C23.2 (1)O1—C1—C2—O32.1 (2)
O11—Zr1—O5—C3176.3 (1)O2—C1—C2—O3177.3 (1)
O7—Zr1—O5—C32.6 (1)Zr1—O5—C3—O6176.4 (1)
O9—Zr1—O5—C3177.6 (1)Zr1—O5—C3—C43.6 (1)
O3—Zr1—O5—C3103.4 (1)Zr1—O7—C4—O8179.3 (1)
O2i—Zr1—O5—C3102.0 (1)Zr1—O7—C4—C30.7 (2)
O4i—Zr1—O5—C350.8 (1)O6—C3—C4—O82.7 (2)
O1—Zr1—O5—C351.0 (1)O5—C3—C4—O8177.3 (1)
O11—Zr1—O7—C4178.2 (1)O6—C3—C4—O7177.3 (1)
O5—Zr1—O7—C40.8 (1)O5—C3—C4—O72.7 (2)
O9—Zr1—O7—C49.2 (1)Zr1—O9—C5—O10178.1 (1)
O3—Zr1—O7—C470.8 (1)Zr1—O9—C5—C61.9 (1)
O2i—Zr1—O7—C476.1 (1)Zr1—O11—C6—O12172.7 (1)
O4i—Zr1—O7—C4144.0 (1)Zr1—O11—C6—C57.2 (1)
O1—Zr1—O7—C4137.3 (1)O10—C5—C6—O123.3 (2)
O11—Zr1—O9—C54.1 (1)O9—C5—C6—O12176.7 (1)
O7—Zr1—O9—C5171.2 (1)O10—C5—C6—O11176.8 (1)
O5—Zr1—O9—C5179.5 (1)O9—C5—C6—O113.2 (2)
O3—Zr1—O9—C5101.1 (1)C10—N1—C7—C854.0 (2)
O2i—Zr1—O9—C597.7 (1)C11—N1—C7—C8176.1 (1)
O4i—Zr1—O9—C551.4 (1)C9—N2—C8—C756.7 (2)
O1—Zr1—O9—C555.3 (1)N1—C7—C8—N254.7 (2)
O7—Zr1—O11—C6169.3 (1)C8—N2—C9—C1057.7 (2)
O5—Zr1—O11—C612.4 (1)C7—N1—C10—C954.8 (2)
O9—Zr1—O11—C66.3 (1)C11—N1—C10—C9177.4 (1)
O3—Zr1—O11—C680.7 (1)N2—C9—C10—N156.6 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O80.85 (1)2.11 (1)2.892 (2)153 (2)
N2—H21···O2iii0.86 (1)2.27 (2)2.948 (2)136 (2)
N2—H21···O5iv0.86 (1)2.19 (2)2.879 (2)137 (2)
N2—H22···O10v0.86 (1)1.99 (1)2.780 (2)153 (2)
N2—H22···O12v0.86 (1)2.46 (2)3.052 (2)127 (2)
Symmetry codes: (iii) x+2, y+1, z+1; (iv) x+1, y+3/2, z+1/2; (v) x+1, y, z+1.
 

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