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The formula unit of the title one-dimensional coordination polymer, {[Zn(C13H12F2N6O)2(H2O)2](ClO4)2}n, which is twice the asymmetric unit, contains a ZnII ion on an inversion centre, two fluconazole [or 2-(2,4-difluoro­phenyl)-1,3-bis­(1,2,4-triazol-1-yl)propan-2-ol] ligands, two water mol­ecules and two perchlorate anions. The fluconazole ligands connect the ZnII atoms through their N4 atoms in a head-to-tail fashion, resulting in the formation of a one-dimensional cationic macrocyclic chain structure. These one-dimensional cationic chains are connected by hydrogen bonds into a two-dimensional layer structure. There is also a π–π supra­molecular inter­action of the benzene rings of the flucanozole ligands between the chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049506/kj2034sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049506/kj2034Isup2.hkl
Contains datablock I

CCDC reference: 633899

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.075
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.82 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O3 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O4 .. 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O4 .. 2.64 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.820 Tmax scaled 0.820 Tmin scaled 0.716 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

catena-Poly[[[diaquazinc(II)]-bis[µ-2-(2,4-difluorophenyl)-1,3- bis(1,2,4-triazol-1-yl)propan-2-ol)-κ2N4:N4]] perchlorate] top
Crystal data top
[Zn(C13H12F2N6O)2(H2O)2](ClO4)2Z = 1
Mr = 912.87F(000) = 464
Triclinic, P1Dx = 1.793 Mg m3
a = 7.9134 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.986 (2) ÅCell parameters from 2716 reflections
c = 11.494 (3) Åθ = 2.2–27.7°
α = 90.194 (3)°µ = 0.99 mm1
β = 94.070 (3)°T = 293 K
γ = 111.031 (3)°Block, colourless
V = 845.2 (3) Å30.28 × 0.22 × 0.20 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2952 independent reflections
Radiation source: fine-focus sealed tube2658 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 69
Tmin = 0.873, Tmax = 1.000k = 1110
4602 measured reflectionsl = 1313
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0422P)2 + 0.2716P]
where P = (Fo2 + 2Fc2)/3
2952 reflections(Δ/σ)max < 0.001
260 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.35 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
Zn10.50000.50000.00000.02152 (11)
F11.2887 (2)0.50104 (16)0.63408 (13)0.0647 (5)
F21.16771 (17)0.19999 (15)0.30452 (12)0.0473 (3)
O10.60706 (19)0.08401 (16)0.34878 (13)0.0350 (3)
H10.52880.01090.31960.053*
O20.72744 (18)0.64946 (14)0.08118 (12)0.0314 (3)
H2A0.81740.63430.10670.047*
H2B0.73880.73740.08110.047*
N10.7889 (2)0.25400 (16)0.15982 (14)0.0229 (3)
N20.9354 (2)0.37890 (17)0.15970 (15)0.0280 (4)
N30.6820 (2)0.41046 (16)0.08685 (13)0.0239 (3)
N40.6735 (2)0.17969 (16)0.27884 (14)0.0253 (4)
N50.5058 (2)0.25305 (19)0.31415 (16)0.0365 (4)
N60.5466 (2)0.34817 (16)0.14618 (14)0.0260 (4)
C10.6420 (3)0.2753 (2)0.11605 (17)0.0266 (4)
H1A0.52650.20490.10700.032*
C20.8627 (3)0.4689 (2)0.11595 (17)0.0267 (4)
H20.93010.56520.10580.032*
C30.8055 (3)0.11828 (19)0.19334 (16)0.0244 (4)
H3A0.92460.11990.17630.029*
H3B0.71560.04100.14650.029*
C40.7802 (3)0.08710 (19)0.32280 (17)0.0255 (4)
C50.8018 (3)0.05812 (19)0.34866 (17)0.0287 (4)
H5A0.92440.05010.33450.034*
H5B0.78610.07750.43060.034*
C60.6950 (3)0.2379 (2)0.17973 (17)0.0277 (4)
H60.79960.20570.13960.033*
C70.4361 (3)0.3521 (2)0.23173 (19)0.0349 (5)
H70.31940.42010.23190.042*
C80.9186 (3)0.20013 (19)0.40559 (16)0.0263 (4)
C90.8633 (3)0.2536 (2)0.50221 (18)0.0378 (5)
H90.74070.22140.51520.045*
C100.9879 (4)0.3540 (3)0.5793 (2)0.0464 (6)
H100.94940.38830.64380.056*
C111.1666 (3)0.4015 (2)0.5597 (2)0.0418 (6)
C121.2307 (3)0.3528 (2)0.46725 (19)0.0386 (5)
H121.35370.38600.45500.046*
C131.1030 (3)0.2517 (2)0.39339 (18)0.0312 (5)
Cl10.21778 (6)0.92409 (5)0.12612 (4)0.02932 (13)
O30.2001 (3)0.9231 (2)0.24779 (16)0.0707 (6)
O40.3915 (2)0.9218 (2)0.10479 (18)0.0557 (5)
O50.0805 (2)0.80299 (17)0.06879 (17)0.0522 (5)
O60.2018 (3)1.05152 (17)0.07847 (17)0.0559 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02002 (17)0.01680 (17)0.02804 (18)0.00764 (12)0.00165 (12)0.00142 (12)
F10.0731 (11)0.0518 (9)0.0558 (9)0.0125 (8)0.0285 (8)0.0253 (7)
F20.0345 (7)0.0589 (9)0.0464 (8)0.0146 (6)0.0019 (6)0.0151 (7)
O10.0280 (8)0.0325 (8)0.0433 (9)0.0091 (6)0.0034 (7)0.0027 (6)
O20.0244 (7)0.0222 (7)0.0479 (9)0.0076 (6)0.0085 (6)0.0073 (6)
N10.0225 (8)0.0165 (7)0.0282 (8)0.0063 (6)0.0027 (6)0.0021 (6)
N20.0231 (8)0.0198 (8)0.0385 (9)0.0057 (7)0.0039 (7)0.0030 (7)
N30.0246 (8)0.0180 (8)0.0290 (8)0.0084 (6)0.0021 (7)0.0016 (6)
N40.0283 (9)0.0173 (8)0.0289 (8)0.0074 (7)0.0012 (7)0.0020 (6)
N50.0332 (10)0.0323 (10)0.0389 (10)0.0047 (8)0.0084 (8)0.0026 (8)
N60.0268 (9)0.0190 (8)0.0319 (9)0.0087 (7)0.0015 (7)0.0001 (7)
C10.0211 (10)0.0203 (9)0.0358 (11)0.0053 (8)0.0037 (8)0.0018 (8)
C20.0252 (10)0.0185 (9)0.0344 (11)0.0060 (8)0.0006 (8)0.0023 (8)
C30.0282 (10)0.0177 (9)0.0283 (10)0.0106 (8)0.0033 (8)0.0009 (7)
C40.0262 (10)0.0209 (9)0.0287 (10)0.0083 (8)0.0007 (8)0.0011 (8)
C50.0350 (11)0.0207 (10)0.0275 (10)0.0084 (8)0.0071 (8)0.0017 (8)
C60.0266 (10)0.0222 (9)0.0339 (11)0.0083 (8)0.0020 (8)0.0012 (8)
C70.0276 (11)0.0308 (11)0.0416 (12)0.0045 (9)0.0055 (9)0.0050 (9)
C80.0338 (11)0.0184 (9)0.0255 (10)0.0090 (8)0.0026 (8)0.0028 (7)
C90.0436 (13)0.0369 (12)0.0325 (11)0.0140 (10)0.0031 (10)0.0023 (9)
C100.0629 (17)0.0436 (13)0.0329 (12)0.0205 (12)0.0017 (11)0.0107 (10)
C110.0560 (16)0.0287 (11)0.0341 (12)0.0112 (11)0.0173 (11)0.0068 (9)
C120.0373 (13)0.0324 (12)0.0400 (13)0.0074 (10)0.0100 (10)0.0008 (9)
C130.0381 (12)0.0285 (10)0.0271 (10)0.0132 (9)0.0028 (9)0.0005 (8)
Cl10.0274 (3)0.0216 (2)0.0368 (3)0.00609 (19)0.0030 (2)0.00065 (19)
O30.1006 (17)0.0764 (14)0.0422 (10)0.0375 (13)0.0202 (11)0.0050 (10)
O40.0288 (9)0.0580 (11)0.0804 (13)0.0154 (8)0.0055 (8)0.0015 (9)
O50.0389 (9)0.0290 (9)0.0741 (12)0.0051 (7)0.0022 (8)0.0076 (8)
O60.0667 (12)0.0287 (9)0.0732 (12)0.0210 (8)0.0097 (10)0.0049 (8)
Geometric parameters (Å, º) top
Zn1—N32.1438 (15)C1—H1A0.9300
Zn1—N3i2.1438 (15)C2—H20.9300
Zn1—O2i2.1580 (13)C3—C41.534 (3)
Zn1—O22.1580 (13)C3—H3A0.9700
Zn1—N6ii2.1797 (16)C3—H3B0.9700
Zn1—N6iii2.1797 (16)C4—C81.529 (3)
F1—C111.357 (2)C4—C51.547 (3)
F2—C131.353 (2)C5—H5A0.9700
O1—C41.412 (2)C5—H5B0.9700
O1—H10.8200C6—H60.9300
O2—H2A0.8502C7—H70.9300
O2—H2B0.8502C8—C131.380 (3)
N1—C11.321 (2)C8—C91.394 (3)
N1—N21.364 (2)C9—C101.386 (3)
N1—C31.458 (2)C9—H90.9300
N2—C21.313 (2)C10—C111.357 (4)
N3—C11.322 (2)C10—H100.9300
N3—C21.352 (2)C11—C121.369 (3)
N4—C61.326 (3)C12—C131.379 (3)
N4—N51.358 (2)C12—H120.9300
N4—C51.463 (2)Cl1—O31.4149 (19)
N5—C71.307 (3)Cl1—O41.4216 (18)
N6—C61.321 (2)Cl1—O51.4236 (16)
N6—C71.353 (3)Cl1—O61.4304 (17)
N6—Zn1iv2.1797 (16)
N3—Zn1—N3i180.0H3A—C3—H3B107.7
N3—Zn1—O2i91.14 (6)O1—C4—C8106.58 (16)
N3i—Zn1—O2i88.86 (6)O1—C4—C3109.51 (15)
N3—Zn1—O288.86 (6)C8—C4—C3113.67 (15)
N3i—Zn1—O291.14 (6)O1—C4—C5111.05 (16)
O2i—Zn1—O2180.00 (7)C8—C4—C5107.14 (15)
N3—Zn1—N6ii89.87 (6)C3—C4—C5108.88 (16)
N3i—Zn1—N6ii90.13 (6)N4—C5—C4114.06 (15)
O2i—Zn1—N6ii90.14 (6)N4—C5—H5A108.7
O2—Zn1—N6ii89.86 (6)C4—C5—H5A108.7
N3—Zn1—N6iii90.13 (6)N4—C5—H5B108.7
N3i—Zn1—N6iii89.87 (6)C4—C5—H5B108.7
O2i—Zn1—N6iii89.86 (6)H5A—C5—H5B107.6
O2—Zn1—N6iii90.14 (6)N6—C6—N4110.25 (18)
N6ii—Zn1—N6iii180.00 (6)N6—C6—H6124.9
C4—O1—H1109.5N4—C6—H6124.9
Zn1—O2—H2A128.1N5—C7—N6114.97 (19)
Zn1—O2—H2B118.2N5—C7—H7122.5
H2A—O2—H2B113.3N6—C7—H7122.5
C1—N1—N2109.65 (15)C13—C8—C9115.86 (18)
C1—N1—C3127.63 (15)C13—C8—C4123.48 (18)
N2—N1—C3122.44 (15)C9—C8—C4120.62 (18)
C2—N2—N1102.31 (15)C10—C9—C8121.2 (2)
C1—N3—C2102.74 (15)C10—C9—H9119.4
C1—N3—Zn1126.28 (13)C8—C9—H9119.4
C2—N3—Zn1130.75 (12)C11—C10—C9119.3 (2)
C6—N4—N5109.76 (16)C11—C10—H10120.4
C6—N4—C5129.36 (17)C9—C10—H10120.4
N5—N4—C5120.86 (16)C10—C11—F1119.5 (2)
C7—N5—N4102.41 (17)C10—C11—C12122.7 (2)
C6—N6—C7102.61 (17)F1—C11—C12117.8 (2)
C6—N6—Zn1iv128.88 (14)C11—C12—C13116.3 (2)
C7—N6—Zn1iv128.24 (13)C11—C12—H12121.8
N1—C1—N3110.57 (16)C13—C12—H12121.8
N1—C1—H1A124.7F2—C13—C12116.1 (2)
N3—C1—H1A124.7F2—C13—C8119.25 (18)
N2—C2—N3114.72 (17)C12—C13—C8124.6 (2)
N2—C2—H2122.6O3—Cl1—O4109.45 (13)
N3—C2—H2122.6O3—Cl1—O5110.80 (12)
N1—C3—C4113.30 (15)O4—Cl1—O5109.41 (11)
N1—C3—H3A108.9O3—Cl1—O6110.12 (12)
C4—C3—H3A108.9O4—Cl1—O6108.51 (12)
N1—C3—H3B108.9O5—Cl1—O6108.52 (11)
C4—C3—H3B108.9
C1—N1—N2—C20.8 (2)C3—C4—C5—N458.7 (2)
C3—N1—N2—C2175.16 (17)C7—N6—C6—N40.2 (2)
O2i—Zn1—N3—C131.54 (17)Zn1iv—N6—C6—N4174.52 (12)
O2—Zn1—N3—C1148.46 (17)N5—N4—C6—N60.3 (2)
N6ii—Zn1—N3—C158.61 (17)C5—N4—C6—N6178.85 (16)
N6iii—Zn1—N3—C1121.39 (17)N4—N5—C7—N60.2 (2)
O2i—Zn1—N3—C2155.00 (17)C6—N6—C7—N50.0 (2)
O2—Zn1—N3—C225.00 (17)Zn1iv—N6—C7—N5174.38 (14)
N6ii—Zn1—N3—C2114.85 (18)O1—C4—C8—C13168.36 (18)
N6iii—Zn1—N3—C265.15 (18)C3—C4—C8—C1347.6 (2)
C6—N4—N5—C70.3 (2)C5—C4—C8—C1372.7 (2)
C5—N4—N5—C7178.94 (17)O1—C4—C8—C914.1 (2)
N2—N1—C1—N30.5 (2)C3—C4—C8—C9134.79 (19)
C3—N1—C1—N3174.51 (17)C5—C4—C8—C9104.9 (2)
C2—N3—C1—N10.0 (2)C13—C8—C9—C100.9 (3)
Zn1—N3—C1—N1174.95 (12)C4—C8—C9—C10178.66 (19)
N1—N2—C2—N30.8 (2)C8—C9—C10—C110.5 (4)
C1—N3—C2—N20.5 (2)C9—C10—C11—F1179.2 (2)
Zn1—N3—C2—N2174.06 (13)C9—C10—C11—C121.1 (4)
C1—N1—C3—C493.6 (2)C10—C11—C12—C130.3 (3)
N2—N1—C3—C493.1 (2)F1—C11—C12—C13179.97 (19)
N1—C3—C4—O158.8 (2)C11—C12—C13—F2177.73 (18)
N1—C3—C4—C860.3 (2)C11—C12—C13—C81.3 (3)
N1—C3—C4—C5179.62 (15)C9—C8—C13—F2177.14 (18)
C6—N4—C5—C495.2 (2)C4—C8—C13—F20.5 (3)
N5—N4—C5—C486.4 (2)C9—C8—C13—C121.8 (3)
O1—C4—C5—N462.0 (2)C4—C8—C13—C12179.53 (19)
C8—C4—C5—N4177.99 (16)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3iv0.822.503.169 (3)139
O1—H1···O4iv0.822.643.272 (3)135
O2—H2B···O6v0.851.992.833 (2)173
O2—H2A···N2vi0.852.142.983 (2)173
C1—H1A···O4iv0.932.643.368 (3)136
C1—H1A···O6iv0.932.473.392 (3)171
C2—H2···O5vii0.932.293.227 (3)176
C3—H3B···O4iv0.972.423.243 (3)143
C5—H5A···O3viii0.972.563.501 (4)164
C6—H6···O5viii0.932.393.280 (3)159
Symmetry codes: (iv) x, y1, z; (v) x+1, y+2, z; (vi) x+2, y+1, z; (vii) x+1, y, z; (viii) x+1, y1, z.
 

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