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In the title compound, [Zn(C11H26N4)(C11H9S)]ClO4, the ZnII atom is five-coordinated by four N atoms from a neutral 1,4,8,12-tetra­azacyclo­penta­decane aza-macrocycle mol­ecule, and one S atom from an azulenylmethane­thiol­ate ligand. Only monomers are found in the crystal. The coordination geometry can be described as trigonal bipyramidal, with the thiol­ate group in an equatorial position. The Zn—N and Zn—S distances are in the usual ranges for this type of complex.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047514/hy2083sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047514/hy2083Isup2.hkl
Contains datablock I

CCDC reference: 674234

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in solvent or counterion
  • R factor = 0.049
  • wR factor = 0.138
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O43 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O44 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.90 Deg. O41 -CL -O41A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.30 Deg. O42 -CL -O42A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.80 Deg. O43 -CL -O43A 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 5858 Count of symmetry unique reflns 3325 Completeness (_total/calc) 176.18% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2533 Fraction of Friedel pairs measured 0.762 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

Comment top

The title compound belongs to a series of zinc thiolate complexes with azamacrocyclic ligands (Notni, Görls et al., 2006), which are potent model systems for a number of zinc enzymes (Schenk et al., 2006). These compounds possess nucleophilic p-methylthiolate or phenylmethylthiolate residues, the nucleophilicity of which is influenced by the nature of the macrocyclic ligand (Notni, Schenk et al., 2006; Notni et al., 2007). In order to gain insight into the electronic properties of the sulfur atom, azulenylmethyl derivatives were believed to allow a qualitative estimation of electron density at the thiolate sulfur employing VIS spectroscopy. However, the project failed since most of the desired complexes were elusive due to degradation processes during synthesis.

In crystalline form, the title compound is air-stable for several months. The crystal structure of the title compound contains a monovalent zinc(II) complex cation and a discrete perchlorate anion as shown in Fig. 1. Within the cation, the ZnII atom is coordinated by four N atoms and one S atom. Whether the coordination polyhedron can be assigned to tetragonal-pyramidal or trigonal-bipyramidal type is a question, which has been discussed in detail before (Notni, Görls et al., 2006). Following the argumentation given therein, we consider the title structure being trigonal-bipyramidal since pairs of opposing short Zn—N bond lengths [2.134 (4) and 2.139 (4) Å] as well as long Zn—N bond lengths [2.235 (3) and 2.272 (4) Å] are found. This is the largest difference between short and long Zn—N bond distances found for this type of zinc complexes (Notni, Görls et al., 2006; Salter et al., 2005). The pair of long N—Zn—N bonds is considered the axis of the trigonal bipyramid, the thiolate group thus being found in the equatorial position. The Zn—S bond length of 2.280 (1)Å is within the usual range for this kind of compounds (2.27–2.32 Å). The N atoms in these complexes are chiral in nature and the absolute configuration could be determined. In analogy to similar zinc–thiolate complexes of 1,4,8,12-tetraazacyclopentadecane, the N-bound H atoms are found in (+ – – –) positions ('+' denotes the H atom being positioned at the thiolate side of the macrocycle and '–' at the opposite side).

Related literature top

For related literature, see: Notni, Görls et al. (2006); Notni, Schenk et al. (2006); Notni et al. (2007); Salter et al. (2005); Schenk et al. (2006).

Experimental top

The title compound was prepared according to the published procedure (Notni, Görls et al., 2006). A solution of zinc perchlorate hexahydrate (0.750 g, 2 mmol) and 1,4,8,12,tetraazacyclopentadecane (0.430 g, 2 mmol) in methanol (20 ml) was heated for 15 min. Then a solution of potassium hydroxide (0.112 g, 2 mmol) and 1-azulenylmethylthiol (0.350 g, 2 mmol) in methanol (5 ml) was added dropwise, whereupon a fine-crystalline precipitate of potassium perchlorate was obtained. This was filtered off, and from the remaining deep-blue solution, blue needle crystals of the title compound precipitated after 5 min which were collected on a filter funnel and dried in vacuum. Yield 66% (0.731 g). m. p. 473.5–475.5 K. Analysis, calculated for C22H35ClN4O4SZn: C 47.83, H 6.39, N 10.14, S 5.80, Cl 6.42%; Found: C 47.81, H 6.42, N 9.94, S 5.70, Cl 6.49%.

Refinement top

H atoms were positioned geometrically and refined as riding, with C—H = 0.95Å (CH) and 0.99Å (CH2), and N—H = 0.93Å and Uiso(H) = 1.2Ueq(C, N). O atoms of the perchlorate group are disordered and they were refined isotropically.

Structure description top

The title compound belongs to a series of zinc thiolate complexes with azamacrocyclic ligands (Notni, Görls et al., 2006), which are potent model systems for a number of zinc enzymes (Schenk et al., 2006). These compounds possess nucleophilic p-methylthiolate or phenylmethylthiolate residues, the nucleophilicity of which is influenced by the nature of the macrocyclic ligand (Notni, Schenk et al., 2006; Notni et al., 2007). In order to gain insight into the electronic properties of the sulfur atom, azulenylmethyl derivatives were believed to allow a qualitative estimation of electron density at the thiolate sulfur employing VIS spectroscopy. However, the project failed since most of the desired complexes were elusive due to degradation processes during synthesis.

In crystalline form, the title compound is air-stable for several months. The crystal structure of the title compound contains a monovalent zinc(II) complex cation and a discrete perchlorate anion as shown in Fig. 1. Within the cation, the ZnII atom is coordinated by four N atoms and one S atom. Whether the coordination polyhedron can be assigned to tetragonal-pyramidal or trigonal-bipyramidal type is a question, which has been discussed in detail before (Notni, Görls et al., 2006). Following the argumentation given therein, we consider the title structure being trigonal-bipyramidal since pairs of opposing short Zn—N bond lengths [2.134 (4) and 2.139 (4) Å] as well as long Zn—N bond lengths [2.235 (3) and 2.272 (4) Å] are found. This is the largest difference between short and long Zn—N bond distances found for this type of zinc complexes (Notni, Görls et al., 2006; Salter et al., 2005). The pair of long N—Zn—N bonds is considered the axis of the trigonal bipyramid, the thiolate group thus being found in the equatorial position. The Zn—S bond length of 2.280 (1)Å is within the usual range for this kind of compounds (2.27–2.32 Å). The N atoms in these complexes are chiral in nature and the absolute configuration could be determined. In analogy to similar zinc–thiolate complexes of 1,4,8,12-tetraazacyclopentadecane, the N-bound H atoms are found in (+ – – –) positions ('+' denotes the H atom being positioned at the thiolate side of the macrocycle and '–' at the opposite side).

For related literature, see: Notni, Görls et al. (2006); Notni, Schenk et al. (2006); Notni et al. (2007); Salter et al. (2005); Schenk et al. (2006).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. The perchlorate anion was omitted for clarity. H atoms have been omitted except those attached to N atoms.
[(1-Azulenyl)methanethiolato-κS](1,4,8,12-tetraazacyclopentadecane-\k4N)zinc(II) perchlorate top
Crystal data top
[Zn(C11H26N4)(C11H9S)]ClO4F(000) = 1160
Mr = 552.42Dx = 1.434 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 18270 reflections
a = 8.0795 (1) Åθ = 2.3–27.5°
b = 13.7163 (3) ŵ = 1.18 mm1
c = 23.0913 (5) ÅT = 183 K
V = 2559.00 (8) Å3Prism, blue
Z = 40.06 × 0.06 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
4978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
φ and ω scansh = 109
18270 measured reflectionsk = 1717
5858 independent reflectionsl = 2829
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0822P)2 + 1.0799P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.038
5858 reflectionsΔρmax = 0.73 e Å3
295 parametersΔρmin = 0.65 e Å3
0 restraintsAbsolute structure: Flack (1983), 2541 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.002 (16)
Crystal data top
[Zn(C11H26N4)(C11H9S)]ClO4V = 2559.00 (8) Å3
Mr = 552.42Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.0795 (1) ŵ = 1.18 mm1
b = 13.7163 (3) ÅT = 183 K
c = 23.0913 (5) Å0.06 × 0.06 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
4978 reflections with I > 2σ(I)
18270 measured reflectionsRint = 0.060
5858 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.138Δρmax = 0.73 e Å3
S = 1.04Δρmin = 0.65 e Å3
5858 reflectionsAbsolute structure: Flack (1983), 2541 Friedel pairs
295 parametersAbsolute structure parameter: 0.002 (16)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn0.54052 (5)0.85174 (3)0.645222 (17)0.03886 (13)
S0.38553 (14)0.73185 (7)0.60351 (5)0.0489 (2)
N10.5011 (5)0.8137 (3)0.74001 (15)0.0618 (11)
H1C0.41440.76910.74000.074*
N20.3875 (5)0.9714 (3)0.67100 (19)0.0631 (10)
H2C0.45801.02370.67790.076*
N30.5965 (5)0.9402 (3)0.56637 (15)0.0554 (9)
H3C0.65220.99650.57760.067*
N40.8012 (4)0.8308 (3)0.65356 (15)0.0541 (9)
H4C0.84610.89260.65890.065*
C10.4320 (9)0.9025 (4)0.7666 (2)0.084 (2)
H1A0.52230.94920.77510.100*
H1B0.37670.88580.80350.100*
C20.3087 (8)0.9488 (5)0.7257 (3)0.0865 (19)
H2A0.21520.90350.71910.104*
H2B0.26431.00930.74320.104*
C30.2676 (7)1.0040 (6)0.6259 (3)0.095 (2)
H3A0.19841.05670.64230.113*
H3B0.19340.94880.61640.113*
C40.3464 (8)1.0407 (5)0.5699 (3)0.0880 (19)
H4A0.25741.06560.54440.106*
H4B0.41931.09640.57950.106*
C50.4450 (8)0.9681 (4)0.5367 (2)0.0724 (14)
H5A0.37670.90920.53010.087*
H5B0.47340.99590.49840.087*
C60.7047 (7)0.8838 (4)0.5260 (2)0.0691 (14)
H6A0.71890.92140.48970.083*
H6B0.64950.82160.51610.083*
C70.8750 (7)0.8621 (5)0.5518 (2)0.0780 (16)
H7A0.94700.83630.52060.094*
H7B0.92420.92410.56520.094*
C80.8765 (7)0.7925 (4)0.6002 (2)0.0718 (14)
H8A0.99250.77380.60840.086*
H8B0.81630.73290.58840.086*
C90.8607 (6)0.7707 (5)0.7035 (2)0.0704 (14)
H9A0.98310.77220.70430.084*
H9B0.82590.70230.69760.084*
C100.7948 (7)0.8062 (5)0.7619 (2)0.0766 (16)
H10A0.87120.78470.79290.092*
H10B0.79290.87840.76200.092*
C110.6270 (9)0.7697 (5)0.7749 (2)0.0811 (17)
H11A0.62470.69820.76880.097*
H11B0.60200.78210.81620.097*
C120.4652 (7)0.6230 (3)0.6411 (2)0.0608 (11)
H12A0.58630.62940.64650.073*
H12B0.41350.61820.67990.073*
C130.4289 (5)0.5323 (3)0.60742 (18)0.0495 (10)
C140.2793 (5)0.4818 (3)0.60754 (16)0.0422 (8)
C150.1353 (6)0.5078 (3)0.63574 (18)0.0547 (10)
H15A0.14180.56570.65820.066*
C160.0175 (7)0.4616 (4)0.6360 (2)0.0653 (12)
H16A0.10210.49420.65710.078*
C170.0651 (7)0.3740 (4)0.6098 (2)0.0698 (13)
H17A0.17560.35370.61690.084*
C180.0282 (8)0.3127 (4)0.5746 (2)0.0692 (13)
H18A0.02730.25580.56140.083*
C190.1875 (7)0.3225 (4)0.5565 (2)0.0665 (13)
H19A0.22660.27230.53170.080*
C200.2998 (6)0.3947 (3)0.5689 (2)0.0546 (10)
C210.4628 (8)0.4009 (4)0.5486 (3)0.0780 (16)
H21A0.51430.35560.52320.094*
C220.5374 (7)0.4838 (4)0.5715 (3)0.0699 (13)
H22A0.64740.50420.56350.084*
Cl0.79877 (18)0.11964 (9)0.68485 (6)0.0683 (3)
O410.8208 (14)0.2153 (8)0.7006 (5)0.091 (3)*0.575 (13)
O420.6918 (15)0.0533 (10)0.7147 (5)0.114 (4)*0.575 (13)
O430.918 (3)0.0559 (17)0.6803 (12)0.221 (9)*0.575 (13)
O440.8335 (15)0.0986 (8)0.6292 (5)0.122 (4)*0.575 (13)
O41A0.823 (3)0.2011 (15)0.7194 (9)0.126 (7)*0.425 (13)
O42A0.6508 (15)0.0964 (10)0.7185 (5)0.082 (3)*0.425 (13)
O43A0.961 (2)0.0861 (11)0.7227 (7)0.120 (5)*0.425 (13)
O44A0.7107 (19)0.1457 (11)0.6300 (6)0.116 (5)*0.425 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0422 (2)0.0405 (2)0.0338 (2)0.00398 (19)0.00309 (18)0.00221 (17)
S0.0618 (6)0.0410 (5)0.0440 (5)0.0080 (4)0.0168 (5)0.0002 (4)
N10.079 (3)0.069 (2)0.0373 (17)0.025 (2)0.0085 (17)0.0057 (17)
N20.054 (2)0.056 (2)0.079 (3)0.0016 (19)0.008 (2)0.015 (2)
N30.071 (2)0.059 (2)0.0365 (17)0.0173 (19)0.0119 (16)0.0113 (15)
N40.0449 (16)0.069 (2)0.0479 (19)0.0047 (17)0.0017 (15)0.0041 (17)
C10.114 (5)0.085 (4)0.052 (3)0.037 (4)0.032 (3)0.025 (3)
C20.070 (3)0.094 (4)0.096 (5)0.003 (3)0.027 (3)0.033 (4)
C30.055 (3)0.107 (5)0.121 (5)0.022 (3)0.019 (3)0.033 (4)
C40.089 (4)0.080 (4)0.095 (5)0.007 (3)0.035 (4)0.015 (3)
C50.085 (4)0.073 (3)0.059 (3)0.001 (3)0.017 (3)0.018 (2)
C60.083 (3)0.088 (4)0.037 (2)0.004 (3)0.014 (2)0.003 (2)
C70.066 (3)0.117 (5)0.051 (3)0.017 (3)0.015 (2)0.014 (3)
C80.062 (3)0.089 (4)0.064 (3)0.005 (3)0.012 (2)0.008 (3)
C90.054 (3)0.082 (3)0.075 (3)0.003 (3)0.024 (2)0.008 (3)
C100.083 (4)0.092 (4)0.055 (3)0.003 (3)0.032 (3)0.001 (3)
C110.111 (5)0.086 (4)0.047 (3)0.019 (4)0.007 (3)0.014 (3)
C120.086 (3)0.044 (2)0.053 (2)0.009 (2)0.025 (3)0.0027 (18)
C130.057 (2)0.0449 (19)0.046 (2)0.0006 (18)0.0149 (18)0.0022 (17)
C140.055 (2)0.0375 (18)0.0337 (17)0.0030 (17)0.0042 (16)0.0017 (15)
C150.075 (3)0.050 (2)0.038 (2)0.008 (2)0.002 (2)0.0029 (18)
C160.067 (3)0.075 (3)0.054 (3)0.004 (3)0.012 (2)0.005 (2)
C170.065 (3)0.077 (3)0.067 (3)0.011 (3)0.007 (2)0.017 (3)
C180.083 (3)0.059 (3)0.066 (3)0.022 (3)0.007 (3)0.002 (2)
C190.075 (3)0.052 (2)0.073 (3)0.007 (2)0.004 (3)0.012 (2)
C200.068 (3)0.044 (2)0.052 (2)0.001 (2)0.001 (2)0.0080 (18)
C210.064 (3)0.067 (3)0.103 (4)0.006 (3)0.016 (3)0.032 (3)
C220.056 (2)0.068 (3)0.086 (3)0.005 (3)0.003 (3)0.005 (3)
Cl0.0732 (7)0.0494 (6)0.0825 (8)0.0190 (5)0.0227 (7)0.0145 (6)
Geometric parameters (Å, º) top
Zn—N42.134 (4)C9—C101.530 (8)
Zn—N22.139 (4)C9—H9A0.9900
Zn—N32.235 (3)C9—H9B0.9900
Zn—N12.272 (4)C10—C111.476 (9)
Zn—S2.2804 (10)C10—H10A0.9900
S—C121.843 (4)C10—H10B0.9900
N1—C111.431 (8)C11—H11A0.9900
N1—C11.474 (7)C11—H11B0.9900
N1—H1C0.9300C12—C131.496 (6)
N2—C21.448 (8)C12—H12A0.9900
N2—C31.491 (8)C12—H12B0.9900
N2—H2C0.9300C13—C221.379 (7)
N3—C51.454 (7)C13—C141.393 (6)
N3—C61.494 (7)C14—C151.380 (6)
N3—H3C0.9300C14—C201.500 (6)
N4—C81.472 (6)C15—C161.388 (7)
N4—C91.496 (6)C15—H15A0.9500
N4—H4C0.9300C16—C171.400 (8)
C1—C21.512 (10)C16—H16A0.9500
C1—H1A0.9900C17—C181.390 (8)
C1—H1B0.9900C17—H17A0.9500
C2—H2A0.9900C18—C191.360 (8)
C2—H2B0.9900C18—H18A0.9500
C3—C41.527 (10)C19—C201.374 (7)
C3—H3A0.9900C19—H19A0.9500
C3—H3B0.9900C20—C211.401 (8)
C4—C51.488 (10)C21—C221.392 (7)
C4—H4A0.9900C21—H21A0.9500
C4—H4B0.9900C22—H22A0.9500
C5—H5A0.9900Cl—O431.31 (2)
C5—H5B0.9900Cl—O441.345 (12)
C6—C71.529 (8)Cl—O411.373 (11)
C6—H6A0.9900Cl—O41A1.39 (2)
C6—H6B0.9900Cl—O421.432 (12)
C7—C81.469 (8)Cl—O42A1.461 (11)
C7—H7A0.9900Cl—O44A1.496 (15)
C7—H7B0.9900Cl—O43A1.640 (16)
C8—H8A0.9900O43—O441.48 (3)
C8—H8B0.9900
N4—Zn—N2130.42 (16)N4—C9—H9A109.0
N4—Zn—N386.95 (15)C10—C9—H9A109.0
N2—Zn—N385.81 (17)N4—C9—H9B109.0
N4—Zn—N191.17 (15)C10—C9—H9B109.0
N2—Zn—N180.05 (17)H9A—C9—H9B107.8
N3—Zn—N1159.70 (15)C11—C10—C9113.0 (5)
N4—Zn—S118.88 (11)C11—C10—H10A109.0
N2—Zn—S110.70 (12)C9—C10—H10A109.0
N3—Zn—S99.13 (10)C11—C10—H10B109.0
N1—Zn—S99.46 (11)C9—C10—H10B109.0
C12—S—Zn101.15 (14)H10A—C10—H10B107.8
C11—N1—C1112.6 (5)N1—C11—C10113.3 (4)
C11—N1—Zn122.7 (3)N1—C11—H11A108.9
C1—N1—Zn105.3 (3)C10—C11—H11A108.9
C11—N1—H1C104.9N1—C11—H11B108.9
C1—N1—H1C104.9C10—C11—H11B108.9
Zn—N1—H1C104.9H11A—C11—H11B107.7
C2—N2—C3112.8 (5)C13—C12—S111.1 (3)
C2—N2—Zn109.4 (4)C13—C12—H12A109.4
C3—N2—Zn114.3 (4)S—C12—H12A109.4
C2—N2—H2C106.6C13—C12—H12B109.4
C3—N2—H2C106.6S—C12—H12B109.4
Zn—N2—H2C106.6H12A—C12—H12B108.0
C5—N3—C6109.5 (4)C22—C13—C14108.2 (4)
C5—N3—Zn110.9 (3)C22—C13—C12126.1 (4)
C6—N3—Zn110.2 (3)C14—C13—C12125.7 (4)
C5—N3—H3C108.7C15—C14—C13127.1 (4)
C6—N3—H3C108.7C15—C14—C20125.4 (4)
Zn—N3—H3C108.7C13—C14—C20107.4 (4)
C8—N4—C9108.4 (4)C14—C15—C16129.4 (4)
C8—N4—Zn112.4 (3)C14—C15—H15A115.3
C9—N4—Zn117.4 (3)C16—C15—H15A115.3
C8—N4—H4C105.9C15—C16—C17129.3 (5)
C9—N4—H4C105.9C15—C16—H16A115.3
Zn—N4—H4C105.9C17—C16—H16A115.3
N1—C1—C2109.7 (4)C18—C17—C16128.6 (5)
N1—C1—H1A109.7C18—C17—H17A115.7
C2—C1—H1A109.7C16—C17—H17A115.7
N1—C1—H1B109.7C19—C18—C17129.3 (5)
C2—C1—H1B109.7C19—C18—H18A115.4
H1A—C1—H1B108.2C17—C18—H18A115.4
N2—C2—C1110.2 (5)C18—C19—C20129.2 (5)
N2—C2—H2A109.6C18—C19—H19A115.4
C1—C2—H2A109.6C20—C19—H19A115.4
N2—C2—H2B109.6C19—C20—C21126.5 (5)
C1—C2—H2B109.6C19—C20—C14128.7 (5)
H2A—C2—H2B108.1C21—C20—C14104.8 (4)
N2—C3—C4114.8 (5)C22—C21—C20109.2 (5)
N2—C3—H3A108.6C22—C21—H21A125.4
C4—C3—H3A108.6C20—C21—H21A125.4
N2—C3—H3B108.6C13—C22—C21110.4 (5)
C4—C3—H3B108.6C13—C22—H22A124.8
H3A—C3—H3B107.5C21—C22—H22A124.8
C5—C4—C3116.0 (5)O43—Cl—O4468.0 (13)
C5—C4—H4A108.3O43—Cl—O41124.5 (12)
C3—C4—H4A108.3O44—Cl—O41115.5 (7)
C5—C4—H4B108.3O43—Cl—O41A119.0 (15)
C3—C4—H4B108.3O44—Cl—O41A133.9 (10)
H4A—C4—H4B107.4O41—Cl—O41A19.9 (9)
N3—C5—C4112.5 (5)O43—Cl—O4293.4 (11)
N3—C5—H5A109.1O44—Cl—O42116.7 (7)
C4—C5—H5A109.1O41—Cl—O42123.9 (8)
N3—C5—H5B109.1O41A—Cl—O42108.6 (11)
C4—C5—H5B109.1O43—Cl—O42A120.1 (11)
H5A—C5—H5B107.8O44—Cl—O42A129.2 (7)
N3—C6—C7112.6 (4)O41—Cl—O42A100.0 (8)
N3—C6—H6A109.1O41A—Cl—O42A89.0 (11)
C7—C6—H6A109.1O42—Cl—O42A27.3 (6)
N3—C6—H6B109.1O43—Cl—O44A116.3 (14)
C7—C6—H6B109.1O44—Cl—O44A48.9 (6)
H6A—C6—H6B107.8O41—Cl—O44A93.2 (8)
C8—C7—C6115.5 (5)O41A—Cl—O44A111.1 (11)
C8—C7—H7A108.4O42—Cl—O44A105.8 (7)
C6—C7—H7A108.4O42A—Cl—O44A96.5 (7)
C8—C7—H7B108.4O43—Cl—O43A42.8 (11)
C6—C7—H7B108.4O44—Cl—O43A106.4 (8)
H7A—C7—H7B107.5O41—Cl—O43A91.3 (8)
C7—C8—N4113.7 (5)O41A—Cl—O43A78.9 (11)
C7—C8—H8A108.8O42—Cl—O43A92.7 (7)
N4—C8—H8A108.8O42A—Cl—O43A107.9 (7)
C7—C8—H8B108.8O44A—Cl—O43A154.0 (8)
N4—C8—H8B108.8Cl—O43—O4457.3 (11)
H8A—C8—H8B107.7Cl—O44—O4354.7 (10)
N4—C9—C10113.1 (5)

Experimental details

Crystal data
Chemical formula[Zn(C11H26N4)(C11H9S)]ClO4
Mr552.42
Crystal system, space groupOrthorhombic, P212121
Temperature (K)183
a, b, c (Å)8.0795 (1), 13.7163 (3), 23.0913 (5)
V3)2559.00 (8)
Z4
Radiation typeMo Kα
µ (mm1)1.18
Crystal size (mm)0.06 × 0.06 × 0.05
Data collection
DiffractometerNonius KappaCCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18270, 5858, 4978
Rint0.060
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.138, 1.04
No. of reflections5858
No. of parameters295
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 0.65
Absolute structureFlack (1983), 2541 Friedel pairs
Absolute structure parameter0.002 (16)

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1990).

Selected geometric parameters (Å, º) top
Zn—N42.134 (4)Zn—N12.272 (4)
Zn—N22.139 (4)Zn—S2.2804 (10)
Zn—N32.235 (3)
N4—Zn—N2130.42 (16)N3—Zn—N1159.70 (15)
N4—Zn—N386.95 (15)N4—Zn—S118.88 (11)
N2—Zn—N385.81 (17)N2—Zn—S110.70 (12)
N4—Zn—N191.17 (15)N3—Zn—S99.13 (10)
N2—Zn—N180.05 (17)N1—Zn—S99.46 (11)
 

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