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The title molecular complex, [Zn(H2O)6](ClO4)2·2C6H8N2O2, consists of neutral 2,5-di­methyl­pyrazine 1,4-dioxide mol­ecules, a hexa­aqua­zinc(II) cation and perchlorate anions, linked through Coulombic attraction and hydrogen bonding. Half the neutral molecules lie in general positions, and the other half are on inversion centers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001005/rn6035sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001005/rn6035Isup2.hkl
Contains datablock I

CCDC reference: 254313

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.054
  • wR factor = 0.141
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Hexaaquazinc(II) bis(perchlorate) 2,5-dimethylpyrazine 1,4-dioxide top
Crystal data top
[Zn(H2O)6](ClO4)2·2C6H8N2O2Dx = 1.678 Mg m3
Mr = 652.65Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 3876 reflections
a = 19.700 (4) Åθ = 2.9–24.2°
b = 13.097 (3) ŵ = 1.24 mm1
c = 20.021 (4) ÅT = 298 K
V = 5166 (2) Å3Rectangular, colorless
Z = 80.50 × 0.15 × 0.11 mm
F(000) = 2688
Data collection top
Bruker SMART CCD area-detector
diffractometer
4805 independent reflections
Radiation source: fine-focus sealed tube3802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
φ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.575, Tmax = 0.875k = 1515
26350 measured reflectionsl = 2422
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0678P)2 + 6.6643P]
where P = (Fo2 + 2Fc2)/3
4805 reflections(Δ/σ)max < 0.001
386 parametersΔρmax = 0.88 e Å3
30 restraintsΔρmin = 0.82 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
Zn10.24282 (2)0.75739 (3)0.48509 (2)0.02657 (17)
C10.3768 (3)0.5835 (5)0.2617 (3)0.0646 (17)
H1A0.36960.63720.29360.097*
H1B0.39450.61190.22110.097*
H1C0.40850.53500.27950.097*
C20.3119 (2)0.5322 (4)0.2478 (2)0.0378 (10)
C30.2826 (2)0.5271 (3)0.1859 (2)0.0401 (11)
H30.30470.55750.15000.048*
C40.1893 (2)0.4364 (3)0.2270 (2)0.0368 (10)
C50.1236 (3)0.3861 (5)0.2141 (3)0.0604 (15)
H5A0.09310.43390.19360.091*
H5B0.10460.36270.25550.091*
H5C0.13030.32900.18480.091*
C60.2192 (2)0.4410 (3)0.2885 (2)0.0366 (10)
H60.19710.41060.32440.044*
C70.0412 (3)0.5774 (5)0.3727 (3)0.0734 (18)
H7A0.07410.63050.37920.110*
H7B0.00280.60430.34910.110*
H7C0.06110.52300.34710.110*
C80.0189 (2)0.5375 (4)0.4386 (2)0.0420 (11)
C90.0467 (2)0.4574 (4)0.5394 (3)0.0456 (12)
H90.07930.42800.56700.055*
C100.4747 (3)0.3845 (5)0.1182 (3)0.0653 (17)
H10A0.44760.42460.14820.098*
H10B0.51680.36710.13950.098*
H10C0.45070.32320.10670.098*
C110.4886 (2)0.4440 (3)0.0570 (2)0.0339 (10)
C120.4479 (2)0.5405 (4)0.0322 (2)0.0393 (11)
H120.41120.56940.05450.047*
N10.27856 (19)0.4871 (3)0.29934 (16)0.0322 (8)
N20.2231 (2)0.4798 (3)0.17510 (16)0.0341 (8)
N30.43600 (17)0.4850 (3)0.02299 (18)0.0321 (8)
N40.06549 (18)0.4933 (3)0.4796 (2)0.0408 (10)
H1O10.2051 (16)0.575 (3)0.450 (2)0.058 (16)*
H2O10.269 (2)0.585 (4)0.420 (3)0.09 (2)*
H1O20.335 (2)0.8595 (19)0.439 (2)0.060 (17)*
H2O20.3548 (19)0.760 (3)0.424 (3)0.09 (2)*
H1O30.306 (3)0.732 (4)0.5947 (11)0.08 (2)*
H2O30.331 (3)0.6576 (19)0.552 (3)0.09 (2)*
H1O40.2640 (18)0.934 (3)0.546 (2)0.08 (2)*
H2O40.1980 (12)0.937 (3)0.522 (2)0.048 (15)*
H1O50.1287 (11)0.726 (4)0.547 (3)0.067 (19)*
H2O50.170 (3)0.650 (3)0.573 (3)0.10 (2)*
H1O60.181 (2)0.8622 (15)0.3969 (19)0.051 (16)*
H2O60.168 (3)0.761 (2)0.3804 (15)0.059 (17)*
Cl20.15380 (7)0.72754 (9)0.23571 (5)0.0434 (3)
Cl30.49517 (6)0.73504 (9)0.40086 (6)0.0451 (3)
O10.23885 (17)0.6142 (2)0.44341 (17)0.0400 (7)
O20.32216 (14)0.8031 (3)0.42184 (15)0.0341 (7)
O30.31702 (18)0.7189 (3)0.55470 (15)0.0443 (8)
O40.23451 (16)0.9029 (2)0.52279 (16)0.0380 (7)
O50.16874 (18)0.7038 (3)0.54975 (18)0.0522 (9)
O60.17265 (15)0.8030 (2)0.41183 (14)0.0319 (6)
O70.30531 (17)0.4890 (2)0.35946 (14)0.0409 (8)
O80.19709 (17)0.4766 (2)0.11459 (14)0.0436 (8)
O90.12848 (15)0.4852 (3)0.4603 (2)0.0551 (10)
O100.37358 (14)0.4718 (3)0.04396 (17)0.0457 (8)
O110.1177 (3)0.8140 (3)0.2567 (2)0.0848 (14)
O120.2061 (3)0.7601 (4)0.1915 (2)0.0924 (16)
O130.1854 (2)0.6805 (3)0.29209 (16)0.0659 (11)
O140.1130 (2)0.6567 (3)0.2022 (2)0.0832 (13)
O150.43744 (19)0.6800 (3)0.4210 (2)0.0805 (14)
O160.5251 (3)0.7815 (5)0.4575 (3)0.137 (2)
O170.5446 (3)0.6701 (4)0.3779 (3)0.1030 (16)
O180.4767 (3)0.8159 (4)0.3614 (3)0.1128 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0273 (3)0.0288 (3)0.0236 (3)0.00279 (19)0.00136 (18)0.00036 (19)
C10.068 (4)0.083 (4)0.043 (3)0.033 (3)0.001 (3)0.008 (3)
C20.047 (3)0.038 (3)0.028 (2)0.006 (2)0.004 (2)0.0003 (19)
C30.056 (3)0.038 (3)0.026 (2)0.011 (2)0.009 (2)0.0038 (19)
C40.049 (3)0.035 (3)0.027 (2)0.003 (2)0.0099 (19)0.0003 (18)
C50.062 (4)0.074 (4)0.045 (3)0.025 (3)0.007 (3)0.003 (3)
C60.051 (3)0.034 (2)0.025 (2)0.003 (2)0.010 (2)0.0050 (18)
C70.063 (4)0.077 (5)0.080 (4)0.001 (3)0.010 (3)0.012 (4)
C80.034 (2)0.035 (3)0.057 (3)0.002 (2)0.004 (2)0.007 (2)
C90.032 (2)0.038 (3)0.067 (3)0.000 (2)0.002 (2)0.008 (2)
C100.047 (3)0.088 (5)0.062 (3)0.001 (3)0.004 (3)0.037 (3)
C110.027 (2)0.036 (3)0.039 (2)0.0003 (18)0.0057 (18)0.0049 (19)
C120.028 (2)0.041 (3)0.050 (3)0.0003 (19)0.008 (2)0.014 (2)
N10.047 (2)0.0266 (19)0.0229 (18)0.0045 (16)0.0052 (16)0.0014 (14)
N20.050 (2)0.032 (2)0.0201 (18)0.0020 (17)0.0046 (16)0.0002 (14)
N30.0230 (18)0.0293 (19)0.044 (2)0.0007 (14)0.0016 (15)0.0036 (16)
N40.026 (2)0.028 (2)0.068 (3)0.0003 (15)0.0049 (19)0.0132 (19)
Cl20.0613 (8)0.0381 (6)0.0309 (6)0.0019 (5)0.0054 (5)0.0006 (5)
Cl30.0337 (6)0.0397 (7)0.0620 (8)0.0016 (5)0.0005 (5)0.0041 (6)
O10.0419 (19)0.0301 (17)0.0478 (19)0.0040 (15)0.0103 (16)0.0065 (15)
O20.0281 (16)0.0409 (19)0.0334 (16)0.0001 (14)0.0032 (13)0.0004 (15)
O30.052 (2)0.053 (2)0.0281 (17)0.0195 (17)0.0078 (15)0.0059 (15)
O40.0334 (17)0.0350 (17)0.0456 (19)0.0084 (14)0.0085 (15)0.0151 (14)
O50.045 (2)0.057 (2)0.054 (2)0.0132 (17)0.0245 (17)0.0272 (19)
O60.0352 (16)0.0339 (18)0.0265 (15)0.0012 (14)0.0012 (13)0.0016 (14)
O70.061 (2)0.0409 (19)0.0205 (15)0.0058 (15)0.0018 (14)0.0004 (13)
O80.059 (2)0.049 (2)0.0231 (15)0.0102 (16)0.0006 (14)0.0003 (14)
O90.0248 (17)0.044 (2)0.097 (3)0.0015 (14)0.0146 (18)0.0124 (19)
O100.0227 (16)0.048 (2)0.067 (2)0.0014 (13)0.0084 (15)0.0159 (17)
O110.113 (4)0.062 (3)0.080 (3)0.034 (3)0.026 (3)0.013 (2)
O120.103 (4)0.130 (4)0.044 (2)0.046 (3)0.002 (2)0.023 (2)
O130.099 (3)0.063 (3)0.0348 (19)0.026 (2)0.0054 (19)0.0057 (18)
O140.090 (3)0.073 (3)0.087 (3)0.023 (2)0.022 (3)0.019 (2)
O150.041 (2)0.066 (3)0.134 (4)0.0044 (18)0.002 (2)0.041 (3)
O160.121 (5)0.146 (6)0.144 (5)0.009 (4)0.017 (4)0.077 (5)
O170.101 (3)0.090 (3)0.118 (3)0.017 (2)0.048 (2)0.002 (2)
O180.106 (3)0.108 (3)0.125 (3)0.004 (2)0.011 (2)0.043 (2)
Geometric parameters (Å, º) top
Zn1—O12.054 (3)C10—H10A0.9600
Zn1—O42.056 (3)C10—H10B0.9600
Zn1—O52.073 (3)C10—H10C0.9600
Zn1—O32.081 (3)C11—N31.352 (5)
Zn1—O22.099 (3)C11—C12ii1.359 (6)
Zn1—O62.102 (3)C12—N31.343 (5)
C1—C21.471 (7)C12—C11ii1.359 (6)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600N1—O71.314 (4)
C1—H1C0.9600N2—O81.316 (4)
C2—N11.358 (5)N3—O101.311 (4)
C2—C31.369 (6)N4—O91.304 (5)
C3—N21.343 (6)Cl2—O141.398 (4)
C3—H30.9300Cl2—O111.402 (4)
C4—N21.359 (5)Cl2—O121.424 (4)
C4—C61.366 (6)Cl2—O131.428 (3)
C4—C51.475 (7)Cl3—O181.371 (5)
C5—H5A0.9600Cl3—O171.372 (5)
C5—H5B0.9600Cl3—O151.406 (4)
C5—H5C0.9600Cl3—O161.416 (6)
C6—N11.335 (6)O1—H1O10.85 (3)
C6—H60.9300O1—H2O10.85 (5)
C7—C81.486 (7)O2—H1O20.85 (3)
C7—H7A0.9600O2—H2O20.86 (4)
C7—H7B0.9600O3—H1O30.85 (3)
C7—H7C0.9600O3—H2O30.85 (3)
C8—N41.361 (6)O4—H1O40.85 (4)
C8—C9i1.367 (6)O4—H2O40.85 (3)
C9—N41.339 (6)O5—H1O50.84 (3)
C9—C8i1.367 (6)O5—H2O50.85 (5)
C9—H90.9300O6—H1O60.849 (11)
C10—C111.478 (6)O6—H2O60.84 (3)
O1—Zn1—O4172.84 (13)H10A—C10—H10B109.5
O1—Zn1—O585.30 (15)C11—C10—H10C109.5
O4—Zn1—O591.61 (15)H10A—C10—H10C109.5
O1—Zn1—O394.47 (14)H10B—C10—H10C109.5
O4—Zn1—O391.97 (13)N3—C11—C12ii117.5 (4)
O5—Zn1—O389.68 (15)N3—C11—C10119.0 (4)
O1—Zn1—O292.51 (13)C12ii—C11—C10123.5 (4)
O4—Zn1—O290.94 (13)N3—C12—C11ii122.8 (4)
O5—Zn1—O2175.98 (13)N3—C12—H12118.6
O3—Zn1—O287.13 (13)C11ii—C12—H12118.6
O1—Zn1—O687.18 (13)O7—N1—C6120.6 (3)
O4—Zn1—O686.59 (12)O7—N1—C2119.6 (4)
O5—Zn1—O693.95 (14)C6—N1—C2119.8 (4)
O3—Zn1—O6176.13 (13)O8—N2—C3120.1 (3)
O2—Zn1—O689.30 (12)O8—N2—C4119.9 (4)
C2—C1—H1A109.5C3—N2—C4119.9 (4)
C2—C1—H1B109.5O10—N3—C12119.9 (3)
H1A—C1—H1B109.5O10—N3—C11120.4 (4)
C2—C1—H1C109.5C12—N3—C11119.7 (4)
H1A—C1—H1C109.5O9—N4—C9120.0 (4)
H1B—C1—H1C109.5O9—N4—C8119.8 (4)
N1—C2—C3117.6 (4)C9—N4—C8120.2 (4)
N1—C2—C1118.3 (4)O14—Cl2—O11112.8 (3)
C3—C2—C1124.0 (4)O14—Cl2—O12108.4 (3)
N2—C3—C2122.3 (4)O11—Cl2—O12108.2 (3)
N2—C3—H3118.8O14—Cl2—O13110.0 (3)
C2—C3—H3118.8O11—Cl2—O13109.4 (2)
N2—C4—C6117.3 (4)O12—Cl2—O13107.8 (3)
N2—C4—C5118.9 (4)O18—Cl3—O17118.3 (3)
C6—C4—C5123.8 (4)O18—Cl3—O15110.3 (3)
C4—C5—H5A109.5O17—Cl3—O15110.6 (3)
C4—C5—H5B109.5O18—Cl3—O16103.9 (4)
H5A—C5—H5B109.5O17—Cl3—O16103.8 (4)
C4—C5—H5C109.5O15—Cl3—O16109.1 (4)
H5A—C5—H5C109.5Zn1—O1—H1O1121 (3)
H5B—C5—H5C109.5Zn1—O1—H2O1128 (3)
N1—C6—C4123.0 (4)H1O1—O1—H2O1111 (3)
N1—C6—H6118.5Zn1—O2—H1O2104 (3)
C4—C6—H6118.5Zn1—O2—H2O2110 (4)
C8—C7—H7A109.5H1O2—O2—H2O2109 (3)
C8—C7—H7B109.5Zn1—O3—H1O3113 (4)
H7A—C7—H7B109.5Zn1—O3—H2O3115 (4)
C8—C7—H7C109.5H1O3—O3—H2O3109 (3)
H7A—C7—H7C109.5Zn1—O4—H1O4126 (3)
H7B—C7—H7C109.5Zn1—O4—H2O4123 (3)
N4—C8—C9i117.7 (5)H1O4—O4—H2O4110 (3)
N4—C8—C7119.1 (4)Zn1—O5—H1O5120 (3)
C9i—C8—C7123.2 (5)Zn1—O5—H2O5127 (4)
N4—C9—C8i122.2 (5)H1O5—O5—H2O5112 (3)
N4—C9—H9118.9Zn1—O6—H1O6112 (3)
C8i—C9—H9118.9Zn1—O6—H2O6114 (3)
C11—C10—H10A109.5H1O6—O6—H2O6111 (3)
C11—C10—H10B109.5
N1—C2—C3—N20.0 (7)C6—C4—N2—C31.7 (6)
C1—C2—C3—N2179.8 (5)C5—C4—N2—C3179.1 (5)
N2—C4—C6—N11.1 (7)C11ii—C12—N3—O10179.3 (4)
C5—C4—C6—N1179.7 (5)C11ii—C12—N3—C111.4 (8)
C4—C6—N1—O7179.7 (4)C12ii—C11—N3—O10179.3 (4)
C4—C6—N1—C20.0 (7)C10—C11—N3—O100.3 (6)
C3—C2—N1—O7179.1 (4)C12ii—C11—N3—C121.3 (7)
C1—C2—N1—O71.1 (7)C10—C11—N3—C12179.1 (5)
C3—C2—N1—C60.6 (6)C8i—C9—N4—O9178.8 (4)
C1—C2—N1—C6179.2 (5)C8i—C9—N4—C80.6 (8)
C2—C3—N2—O8179.8 (4)C9i—C8—N4—O9178.9 (4)
C2—C3—N2—C41.2 (7)C7—C8—N4—O91.0 (7)
C6—C4—N2—O8179.3 (4)C9i—C8—N4—C90.6 (7)
C5—C4—N2—O80.1 (6)C7—C8—N4—C9179.6 (5)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1O3···O12iii0.85 (3)1.95 (2)2.789 (5)168 (5)
O4—H1O4···O8iii0.85 (4)1.96 (2)2.772 (4)160 (5)
O5—H2O5···O8iv0.85 (5)1.93 (5)2.754 (5)165 (5)
O1—H2O1···O70.85 (5)1.89 (5)2.688 (4)157 (5)
O6—H2O6···O130.84 (3)2.08 (2)2.895 (5)161 (5)
O2—H2O2···O150.86 (4)1.94 (4)2.785 (5)171 (6)
O2—H2O2···Cl30.86 (4)2.82 (4)3.548 (3)144 (5)
O5—H1O5···O16v0.84 (3)2.04 (2)2.839 (8)157 (5)
O4—H2O4···O10iii0.85 (3)1.90 (2)2.721 (4)163 (4)
O3—H2O3···O10iv0.85 (3)1.90 (3)2.744 (5)173 (6)
O1—H1O1···O90.85 (3)1.93 (4)2.774 (4)177 (5)
O6—H1O6···O7vi0.85 (1)1.84 (1)2.688 (4)175 (5)
O2—H1O2···O9vi0.85 (3)1.85 (2)2.688 (5)169 (5)
Symmetry codes: (iii) x+1/2, y+3/2, z+1/2; (iv) x, y+1, z+1/2; (v) x1/2, y+3/2, z+1; (vi) x+1/2, y+1/2, z.
 

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