catena-Poly[[[diaqua­zinc(II)]-bis­[μ-2-(2,4-difluoro­phenyl)-1,3-bis­(1,2,4-triazol-1-yl)propan-2-ol-κ²N⁴:N⁴]] bis(perchlorate)]

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 Zn^II 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 Zn^II 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.

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

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]

Crystal data

[Zn(C13H12F2N6O)2(H2O)2](ClO4)2	Z = 1
Mr = 912.87	F(000) = 464
Triclinic, P1	Dx = 1.793 Mg m^−3
a = 7.9134 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.986 (2) Å	Cell parameters from 2716 reflections
c = 11.494 (3) Å	θ = 2.2–27.7°
α = 90.194 (3)°	µ = 0.99 mm^−1
β = 94.070 (3)°	T = 293 K
γ = 111.031 (3)°	Block, colourless
V = 845.2 (3) Å^3	0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	2658 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→9
Tmin = 0.873, Tmax = 1.000	k = −11→10
4602 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0422P)^2 + 0.2716P] where P = (Fo^2 + 2Fc^2)/3
2952 reflections	(Δ/σ)max < 0.001
260 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.5000	0.0000	0.02152 (11)
F1	1.2887 (2)	0.50104 (16)	0.63408 (13)	0.0647 (5)
F2	1.16771 (17)	0.19999 (15)	0.30452 (12)	0.0473 (3)
O1	0.60706 (19)	0.08401 (16)	0.34878 (13)	0.0350 (3)
H1	0.5288	0.0109	0.3196	0.053*
O2	0.72744 (18)	0.64946 (14)	−0.08118 (12)	0.0314 (3)
H2A	0.8174	0.6343	−0.1067	0.047*
H2B	0.7388	0.7374	−0.0811	0.047*
N1	0.7889 (2)	0.25400 (16)	0.15982 (14)	0.0229 (3)
N2	0.9354 (2)	0.37890 (17)	0.15970 (15)	0.0280 (4)
N3	0.6820 (2)	0.41046 (16)	0.08685 (13)	0.0239 (3)
N4	0.6735 (2)	−0.17969 (16)	0.27884 (14)	0.0253 (4)
N5	0.5058 (2)	−0.25305 (19)	0.31415 (16)	0.0365 (4)
N6	0.5466 (2)	−0.34817 (16)	0.14618 (14)	0.0260 (4)
C1	0.6420 (3)	0.2753 (2)	0.11605 (17)	0.0266 (4)
H1A	0.5265	0.2049	0.1070	0.032*
C2	0.8627 (3)	0.4689 (2)	0.11595 (17)	0.0267 (4)
H2	0.9301	0.5652	0.1058	0.032*
C3	0.8055 (3)	0.11828 (19)	0.19334 (16)	0.0244 (4)
H3A	0.9246	0.1199	0.1763	0.029*
H3B	0.7156	0.0410	0.1465	0.029*
C4	0.7802 (3)	0.08710 (19)	0.32280 (17)	0.0255 (4)
C5	0.8018 (3)	−0.05812 (19)	0.34866 (17)	0.0287 (4)
H5A	0.9244	−0.0501	0.3345	0.034*
H5B	0.7861	−0.0775	0.4306	0.034*
C6	0.6950 (3)	−0.2379 (2)	0.17973 (17)	0.0277 (4)
H6	0.7996	−0.2057	0.1396	0.033*
C7	0.4361 (3)	−0.3521 (2)	0.23173 (19)	0.0349 (5)
H7	0.3194	−0.4201	0.2319	0.042*
C8	0.9186 (3)	0.20013 (19)	0.40559 (16)	0.0263 (4)
C9	0.8633 (3)	0.2536 (2)	0.50221 (18)	0.0378 (5)
H9	0.7407	0.2214	0.5152	0.045*
C10	0.9879 (4)	0.3540 (3)	0.5793 (2)	0.0464 (6)
H10	0.9494	0.3883	0.6438	0.056*
C11	1.1666 (3)	0.4015 (2)	0.5597 (2)	0.0418 (6)
C12	1.2307 (3)	0.3528 (2)	0.46725 (19)	0.0386 (5)
H12	1.3537	0.3860	0.4550	0.046*
C13	1.1030 (3)	0.2517 (2)	0.39339 (18)	0.0312 (5)
Cl1	0.21778 (6)	0.92409 (5)	0.12612 (4)	0.02932 (13)
O3	0.2001 (3)	0.9231 (2)	0.24779 (16)	0.0707 (6)
O4	0.3915 (2)	0.9218 (2)	0.10479 (18)	0.0557 (5)
O5	0.0805 (2)	0.80299 (17)	0.06879 (17)	0.0522 (5)
O6	0.2018 (3)	1.05152 (17)	0.07847 (17)	0.0559 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02002 (17)	0.01680 (17)	0.02804 (18)	0.00764 (12)	−0.00165 (12)	0.00142 (12)
F1	0.0731 (11)	0.0518 (9)	0.0558 (9)	0.0125 (8)	−0.0285 (8)	−0.0253 (7)
F2	0.0345 (7)	0.0589 (9)	0.0464 (8)	0.0146 (6)	0.0019 (6)	−0.0151 (7)
O1	0.0280 (8)	0.0325 (8)	0.0433 (9)	0.0091 (6)	0.0034 (7)	−0.0027 (6)
O2	0.0244 (7)	0.0222 (7)	0.0479 (9)	0.0076 (6)	0.0085 (6)	0.0073 (6)
N1	0.0225 (8)	0.0165 (7)	0.0282 (8)	0.0063 (6)	−0.0027 (6)	0.0021 (6)
N2	0.0231 (8)	0.0198 (8)	0.0385 (9)	0.0057 (7)	−0.0039 (7)	0.0030 (7)
N3	0.0246 (8)	0.0180 (8)	0.0290 (8)	0.0084 (6)	−0.0021 (7)	0.0016 (6)
N4	0.0283 (9)	0.0173 (8)	0.0289 (8)	0.0074 (7)	−0.0012 (7)	0.0020 (6)
N5	0.0332 (10)	0.0323 (10)	0.0389 (10)	0.0047 (8)	0.0084 (8)	−0.0026 (8)
N6	0.0268 (9)	0.0190 (8)	0.0319 (9)	0.0087 (7)	−0.0015 (7)	0.0001 (7)
C1	0.0211 (10)	0.0203 (9)	0.0358 (11)	0.0053 (8)	−0.0037 (8)	0.0018 (8)
C2	0.0252 (10)	0.0185 (9)	0.0344 (11)	0.0060 (8)	−0.0006 (8)	0.0023 (8)
C3	0.0282 (10)	0.0177 (9)	0.0283 (10)	0.0106 (8)	−0.0033 (8)	0.0009 (7)
C4	0.0262 (10)	0.0209 (9)	0.0287 (10)	0.0083 (8)	−0.0007 (8)	0.0011 (8)
C5	0.0350 (11)	0.0207 (10)	0.0275 (10)	0.0084 (8)	−0.0071 (8)	0.0017 (8)
C6	0.0266 (10)	0.0222 (9)	0.0339 (11)	0.0083 (8)	0.0020 (8)	0.0012 (8)
C7	0.0276 (11)	0.0308 (11)	0.0416 (12)	0.0045 (9)	0.0055 (9)	−0.0050 (9)
C8	0.0338 (11)	0.0184 (9)	0.0255 (10)	0.0090 (8)	−0.0026 (8)	0.0028 (7)
C9	0.0436 (13)	0.0369 (12)	0.0325 (11)	0.0140 (10)	0.0031 (10)	−0.0023 (9)
C10	0.0629 (17)	0.0436 (13)	0.0329 (12)	0.0205 (12)	−0.0017 (11)	−0.0107 (10)
C11	0.0560 (16)	0.0287 (11)	0.0341 (12)	0.0112 (11)	−0.0173 (11)	−0.0068 (9)
C12	0.0373 (13)	0.0324 (12)	0.0400 (13)	0.0074 (10)	−0.0100 (10)	0.0008 (9)
C13	0.0381 (12)	0.0285 (10)	0.0271 (10)	0.0132 (9)	−0.0028 (9)	−0.0005 (8)
Cl1	0.0274 (3)	0.0216 (2)	0.0368 (3)	0.00609 (19)	0.0030 (2)	0.00065 (19)
O3	0.1006 (17)	0.0764 (14)	0.0422 (10)	0.0375 (13)	0.0202 (11)	0.0050 (10)
O4	0.0288 (9)	0.0580 (11)	0.0804 (13)	0.0154 (8)	0.0055 (8)	−0.0015 (9)
O5	0.0389 (9)	0.0290 (9)	0.0741 (12)	−0.0051 (7)	0.0022 (8)	−0.0076 (8)
O6	0.0667 (12)	0.0287 (9)	0.0732 (12)	0.0210 (8)	−0.0097 (10)	0.0049 (8)

Geometric parameters (Å, º)

Zn1—N3	2.1438 (15)	C1—H1A	0.9300
Zn1—N3^i	2.1438 (15)	C2—H2	0.9300
Zn1—O2^i	2.1580 (13)	C3—C4	1.534 (3)
Zn1—O2	2.1580 (13)	C3—H3A	0.9700
Zn1—N6^ii	2.1797 (16)	C3—H3B	0.9700
Zn1—N6^iii	2.1797 (16)	C4—C8	1.529 (3)
F1—C11	1.357 (2)	C4—C5	1.547 (3)
F2—C13	1.353 (2)	C5—H5A	0.9700
O1—C4	1.412 (2)	C5—H5B	0.9700
O1—H1	0.8200	C6—H6	0.9300
O2—H2A	0.8502	C7—H7	0.9300
O2—H2B	0.8502	C8—C13	1.380 (3)
N1—C1	1.321 (2)	C8—C9	1.394 (3)
N1—N2	1.364 (2)	C9—C10	1.386 (3)
N1—C3	1.458 (2)	C9—H9	0.9300
N2—C2	1.313 (2)	C10—C11	1.357 (4)
N3—C1	1.322 (2)	C10—H10	0.9300
N3—C2	1.352 (2)	C11—C12	1.369 (3)
N4—C6	1.326 (3)	C12—C13	1.379 (3)
N4—N5	1.358 (2)	C12—H12	0.9300
N4—C5	1.463 (2)	Cl1—O3	1.4149 (19)
N5—C7	1.307 (3)	Cl1—O4	1.4216 (18)
N6—C6	1.321 (2)	Cl1—O5	1.4236 (16)
N6—C7	1.353 (3)	Cl1—O6	1.4304 (17)
N6—Zn1^iv	2.1797 (16)
N3—Zn1—N3^i	180.0	H3A—C3—H3B	107.7
N3—Zn1—O2^i	91.14 (6)	O1—C4—C8	106.58 (16)
N3^i—Zn1—O2^i	88.86 (6)	O1—C4—C3	109.51 (15)
N3—Zn1—O2	88.86 (6)	C8—C4—C3	113.67 (15)
N3^i—Zn1—O2	91.14 (6)	O1—C4—C5	111.05 (16)
O2^i—Zn1—O2	180.00 (7)	C8—C4—C5	107.14 (15)
N3—Zn1—N6^ii	89.87 (6)	C3—C4—C5	108.88 (16)
N3^i—Zn1—N6^ii	90.13 (6)	N4—C5—C4	114.06 (15)
O2^i—Zn1—N6^ii	90.14 (6)	N4—C5—H5A	108.7
O2—Zn1—N6^ii	89.86 (6)	C4—C5—H5A	108.7
N3—Zn1—N6^iii	90.13 (6)	N4—C5—H5B	108.7
N3^i—Zn1—N6^iii	89.87 (6)	C4—C5—H5B	108.7
O2^i—Zn1—N6^iii	89.86 (6)	H5A—C5—H5B	107.6
O2—Zn1—N6^iii	90.14 (6)	N6—C6—N4	110.25 (18)
N6^ii—Zn1—N6^iii	180.00 (6)	N6—C6—H6	124.9
C4—O1—H1	109.5	N4—C6—H6	124.9
Zn1—O2—H2A	128.1	N5—C7—N6	114.97 (19)
Zn1—O2—H2B	118.2	N5—C7—H7	122.5
H2A—O2—H2B	113.3	N6—C7—H7	122.5
C1—N1—N2	109.65 (15)	C13—C8—C9	115.86 (18)
C1—N1—C3	127.63 (15)	C13—C8—C4	123.48 (18)
N2—N1—C3	122.44 (15)	C9—C8—C4	120.62 (18)
C2—N2—N1	102.31 (15)	C10—C9—C8	121.2 (2)
C1—N3—C2	102.74 (15)	C10—C9—H9	119.4
C1—N3—Zn1	126.28 (13)	C8—C9—H9	119.4
C2—N3—Zn1	130.75 (12)	C11—C10—C9	119.3 (2)
C6—N4—N5	109.76 (16)	C11—C10—H10	120.4
C6—N4—C5	129.36 (17)	C9—C10—H10	120.4
N5—N4—C5	120.86 (16)	C10—C11—F1	119.5 (2)
C7—N5—N4	102.41 (17)	C10—C11—C12	122.7 (2)
C6—N6—C7	102.61 (17)	F1—C11—C12	117.8 (2)
C6—N6—Zn1^iv	128.88 (14)	C11—C12—C13	116.3 (2)
C7—N6—Zn1^iv	128.24 (13)	C11—C12—H12	121.8
N1—C1—N3	110.57 (16)	C13—C12—H12	121.8
N1—C1—H1A	124.7	F2—C13—C12	116.1 (2)
N3—C1—H1A	124.7	F2—C13—C8	119.25 (18)
N2—C2—N3	114.72 (17)	C12—C13—C8	124.6 (2)
N2—C2—H2	122.6	O3—Cl1—O4	109.45 (13)
N3—C2—H2	122.6	O3—Cl1—O5	110.80 (12)
N1—C3—C4	113.30 (15)	O4—Cl1—O5	109.41 (11)
N1—C3—H3A	108.9	O3—Cl1—O6	110.12 (12)
C4—C3—H3A	108.9	O4—Cl1—O6	108.51 (12)
N1—C3—H3B	108.9	O5—Cl1—O6	108.52 (11)
C4—C3—H3B	108.9
C1—N1—N2—C2	0.8 (2)	C3—C4—C5—N4	−58.7 (2)
C3—N1—N2—C2	175.16 (17)	C7—N6—C6—N4	−0.2 (2)
O2^i—Zn1—N3—C1	31.54 (17)	Zn1^iv—N6—C6—N4	−174.52 (12)
O2—Zn1—N3—C1	−148.46 (17)	N5—N4—C6—N6	0.3 (2)
N6^ii—Zn1—N3—C1	−58.61 (17)	C5—N4—C6—N6	178.85 (16)
N6^iii—Zn1—N3—C1	121.39 (17)	N4—N5—C7—N6	0.2 (2)
O2^i—Zn1—N3—C2	−155.00 (17)	C6—N6—C7—N5	0.0 (2)
O2—Zn1—N3—C2	25.00 (17)	Zn1^iv—N6—C7—N5	174.38 (14)
N6^ii—Zn1—N3—C2	114.85 (18)	O1—C4—C8—C13	−168.36 (18)
N6^iii—Zn1—N3—C2	−65.15 (18)	C3—C4—C8—C13	−47.6 (2)
C6—N4—N5—C7	−0.3 (2)	C5—C4—C8—C13	72.7 (2)
C5—N4—N5—C7	−178.94 (17)	O1—C4—C8—C9	14.1 (2)
N2—N1—C1—N3	−0.5 (2)	C3—C4—C8—C9	134.79 (19)
C3—N1—C1—N3	−174.51 (17)	C5—C4—C8—C9	−104.9 (2)
C2—N3—C1—N1	0.0 (2)	C13—C8—C9—C10	0.9 (3)
Zn1—N3—C1—N1	174.95 (12)	C4—C8—C9—C10	178.66 (19)
N1—N2—C2—N3	−0.8 (2)	C8—C9—C10—C11	0.5 (4)
C1—N3—C2—N2	0.5 (2)	C9—C10—C11—F1	179.2 (2)
Zn1—N3—C2—N2	−174.06 (13)	C9—C10—C11—C12	−1.1 (4)
C1—N1—C3—C4	−93.6 (2)	C10—C11—C12—C13	0.3 (3)
N2—N1—C3—C4	93.1 (2)	F1—C11—C12—C13	179.97 (19)
N1—C3—C4—O1	58.8 (2)	C11—C12—C13—F2	−177.73 (18)
N1—C3—C4—C8	−60.3 (2)	C11—C12—C13—C8	1.3 (3)
N1—C3—C4—C5	−179.62 (15)	C9—C8—C13—F2	177.14 (18)
C6—N4—C5—C4	95.2 (2)	C4—C8—C13—F2	−0.5 (3)
N5—N4—C5—C4	−86.4 (2)	C9—C8—C13—C12	−1.8 (3)
O1—C4—C5—N4	62.0 (2)	C4—C8—C13—C12	−179.53 (19)
C8—C4—C5—N4	177.99 (16)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z; (iii) x, y+1, z; (iv) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^iv	0.82	2.50	3.169 (3)	139
O1—H1···O4^iv	0.82	2.64	3.272 (3)	135
O2—H2B···O6^v	0.85	1.99	2.833 (2)	173
O2—H2A···N2^vi	0.85	2.14	2.983 (2)	173
C1—H1A···O4^iv	0.93	2.64	3.368 (3)	136
C1—H1A···O6^iv	0.93	2.47	3.392 (3)	171
C2—H2···O5^vii	0.93	2.29	3.227 (3)	176
C3—H3B···O4^iv	0.97	2.42	3.243 (3)	143
C5—H5A···O3^viii	0.97	2.56	3.501 (4)	164
C6—H6···O5^viii	0.93	2.39	3.280 (3)	159

Symmetry codes: (iv) x, y−1, z; (v) −x+1, −y+2, −z; (vi) −x+2, −y+1, −z; (vii) x+1, y, z; (viii) x+1, y−1, z.