[(1-Azulen-yl)methane-thiol-ato-κS](1,4,8,12-tetra-azacyclo-penta-decane-κN)zinc(II) perchlorate.

In the title compound, [Zn(C(11)H(26)N(4))(C(11)H(9)S)]ClO(4), the Zn(II) atom is five-coordinated by four N atoms from a neutral 1,4,8,12-tetra-azacyclo-penta-decane aza-macrocycle mol-ecule, and one S atom from an azulenylmethane-thiol-ate ligand. Only monomers are found in the crystal. The coordination geometry can be described as trigonal bipyramidal, with the thiol-ate group in an equatorial position. The Zn-N and Zn-S distances are in the usual ranges for this type of complex.

Related literature

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

Crystal data

[Zn(C11n class="CellLine">H26N4)(C11H9S)]ClO4

M = 552.42

Orthorhombic,

a = 8.0795 (1) Å

b = 13.7163 (3) Å

c = 23.0913 (5) Å

V = 2559.00 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.18 mm−1

T = 183 (2) K

0.06 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

18270 measured reflections

5858 independent reflections

4978 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.138

S = 1.04

5858 reflections

295 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.65 e Å−3

Absolute structure: Flack (1983 ▶), 2541 Friedel pairs

Flack parameter: 0.002 (16)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807047514/hy2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807047514/hy2083Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C11H26N4)(C11H9S)]ClO4	F000 = 1160
Mr = 552.42	Dx = 1.434 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18270 reflections
a = 8.0795 (1) Å	θ = 2.3–27.5º
b = 13.7163 (3) Å	µ = 1.18 mm−1
c = 23.0913 (5) Å	T = 183 (2) K
V = 2559.00 (8) Å3	Prism, blue
Z = 4	0.06 × 0.06 × 0.05 mm

Nonius KappaCCD diffractometer	4978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Monochromator: graphite	θmax = 27.5º
T = 183(2) K	θmin = 2.3º
φ and ω scans	h = −10→9
Absorption correction: none	k = −17→17
18270 measured reflections	l = −28→29
5858 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0822P)2 + 1.0799P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138	(Δ/σ)max = 0.038
S = 1.04	Δρmax = 0.73 e Å−3
5858 reflections	Δρmin = −0.65 e Å−3
295 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2541 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.002 (16)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn	0.54052 (5)	0.85174 (3)	0.645222 (17)	0.03886 (13)
S	0.38553 (14)	0.73185 (7)	0.60351 (5)	0.0489 (2)
N1	0.5011 (5)	0.8137 (3)	0.74001 (15)	0.0618 (11)
H1C	0.4144	0.7691	0.7400	0.074*
N2	0.3875 (5)	0.9714 (3)	0.67100 (19)	0.0631 (10)
H2C	0.4580	1.0237	0.6779	0.076*
N3	0.5965 (5)	0.9402 (3)	0.56637 (15)	0.0554 (9)
H3C	0.6522	0.9965	0.5776	0.067*
N4	0.8012 (4)	0.8308 (3)	0.65356 (15)	0.0541 (9)
H4C	0.8461	0.8926	0.6589	0.065*
C1	0.4320 (9)	0.9025 (4)	0.7666 (2)	0.084 (2)
H1A	0.5223	0.9492	0.7751	0.100*
H1B	0.3767	0.8858	0.8035	0.100*
C2	0.3087 (8)	0.9488 (5)	0.7257 (3)	0.0865 (19)
H2A	0.2152	0.9035	0.7191	0.104*
H2B	0.2643	1.0093	0.7432	0.104*
C3	0.2676 (7)	1.0040 (6)	0.6259 (3)	0.095 (2)
H3A	0.1984	1.0567	0.6423	0.113*
H3B	0.1934	0.9488	0.6164	0.113*
C4	0.3464 (8)	1.0407 (5)	0.5699 (3)	0.0880 (19)
H4A	0.2574	1.0656	0.5444	0.106*
H4B	0.4193	1.0964	0.5795	0.106*
C5	0.4450 (8)	0.9681 (4)	0.5367 (2)	0.0724 (14)
H5A	0.3767	0.9092	0.5301	0.087*
H5B	0.4734	0.9959	0.4984	0.087*
C6	0.7047 (7)	0.8838 (4)	0.5260 (2)	0.0691 (14)
H6A	0.7189	0.9214	0.4897	0.083*
H6B	0.6495	0.8216	0.5161	0.083*
C7	0.8750 (7)	0.8621 (5)	0.5518 (2)	0.0780 (16)
H7A	0.9470	0.8363	0.5206	0.094*
H7B	0.9242	0.9241	0.5652	0.094*
C8	0.8765 (7)	0.7925 (4)	0.6002 (2)	0.0718 (14)
H8A	0.9925	0.7738	0.6084	0.086*
H8B	0.8163	0.7329	0.5884	0.086*
C9	0.8607 (6)	0.7707 (5)	0.7035 (2)	0.0704 (14)
H9A	0.9831	0.7722	0.7043	0.084*
H9B	0.8259	0.7023	0.6976	0.084*
C10	0.7948 (7)	0.8062 (5)	0.7619 (2)	0.0766 (16)
H10A	0.8712	0.7847	0.7929	0.092*
H10B	0.7929	0.8784	0.7620	0.092*
C11	0.6270 (9)	0.7697 (5)	0.7749 (2)	0.0811 (17)
H11A	0.6247	0.6982	0.7688	0.097*
H11B	0.6020	0.7821	0.8162	0.097*
C12	0.4652 (7)	0.6230 (3)	0.6411 (2)	0.0608 (11)
H12A	0.5863	0.6294	0.6465	0.073*
H12B	0.4135	0.6182	0.6799	0.073*
C13	0.4289 (5)	0.5323 (3)	0.60742 (18)	0.0495 (10)
C14	0.2793 (5)	0.4818 (3)	0.60754 (16)	0.0422 (8)
C15	0.1353 (6)	0.5078 (3)	0.63574 (18)	0.0547 (10)
H15A	0.1418	0.5657	0.6582	0.066*
C16	−0.0175 (7)	0.4616 (4)	0.6360 (2)	0.0653 (12)
H16A	−0.1021	0.4942	0.6571	0.078*
C17	−0.0651 (7)	0.3740 (4)	0.6098 (2)	0.0698 (13)
H17A	−0.1756	0.3537	0.6169	0.084*
C18	0.0282 (8)	0.3127 (4)	0.5746 (2)	0.0692 (13)
H18A	−0.0273	0.2558	0.5614	0.083*
C19	0.1875 (7)	0.3225 (4)	0.5565 (2)	0.0665 (13)
H19A	0.2266	0.2723	0.5317	0.080*
C20	0.2998 (6)	0.3947 (3)	0.5689 (2)	0.0546 (10)
C21	0.4628 (8)	0.4009 (4)	0.5486 (3)	0.0780 (16)
H21A	0.5143	0.3556	0.5232	0.094*
C22	0.5374 (7)	0.4838 (4)	0.5715 (3)	0.0699 (13)
H22A	0.6474	0.5042	0.5635	0.084*
Cl	0.79877 (18)	0.11964 (9)	0.68485 (6)	0.0683 (3)
O41	0.8208 (14)	0.2153 (8)	0.7006 (5)	0.091 (3)*	0.575 (13)
O42	0.6918 (15)	0.0533 (10)	0.7147 (5)	0.114 (4)*	0.575 (13)
O43	0.918 (3)	0.0559 (17)	0.6803 (12)	0.221 (9)*	0.575 (13)
O44	0.8335 (15)	0.0986 (8)	0.6292 (5)	0.122 (4)*	0.575 (13)
O41A	0.823 (3)	0.2011 (15)	0.7194 (9)	0.126 (7)*	0.425 (13)
O42A	0.6508 (15)	0.0964 (10)	0.7185 (5)	0.082 (3)*	0.425 (13)
O43A	0.961 (2)	0.0861 (11)	0.7227 (7)	0.120 (5)*	0.425 (13)
O44A	0.7107 (19)	0.1457 (11)	0.6300 (6)	0.116 (5)*	0.425 (13)

	U11	U22	U33	U12	U13	U23
Zn	0.0422 (2)	0.0405 (2)	0.0338 (2)	−0.00398 (19)	−0.00309 (18)	−0.00221 (17)
S	0.0618 (6)	0.0410 (5)	0.0440 (5)	−0.0080 (4)	−0.0168 (5)	−0.0002 (4)
N1	0.079 (3)	0.069 (2)	0.0373 (17)	−0.025 (2)	0.0085 (17)	−0.0057 (17)
N2	0.054 (2)	0.056 (2)	0.079 (3)	−0.0016 (19)	0.008 (2)	−0.015 (2)
N3	0.071 (2)	0.059 (2)	0.0365 (17)	−0.0173 (19)	−0.0119 (16)	0.0113 (15)
N4	0.0449 (16)	0.069 (2)	0.0479 (19)	−0.0047 (17)	0.0017 (15)	−0.0041 (17)
C1	0.114 (5)	0.085 (4)	0.052 (3)	−0.037 (4)	0.032 (3)	−0.025 (3)
C2	0.070 (3)	0.094 (4)	0.096 (5)	−0.003 (3)	0.027 (3)	−0.033 (4)
C3	0.055 (3)	0.107 (5)	0.121 (5)	0.022 (3)	−0.019 (3)	−0.033 (4)
C4	0.089 (4)	0.080 (4)	0.095 (5)	0.007 (3)	−0.035 (4)	0.015 (3)
C5	0.085 (4)	0.073 (3)	0.059 (3)	0.001 (3)	−0.017 (3)	0.018 (2)
C6	0.083 (3)	0.088 (4)	0.037 (2)	−0.004 (3)	0.014 (2)	0.003 (2)
C7	0.066 (3)	0.117 (5)	0.051 (3)	−0.017 (3)	0.015 (2)	−0.014 (3)
C8	0.062 (3)	0.089 (4)	0.064 (3)	−0.005 (3)	0.012 (2)	−0.008 (3)
C9	0.054 (3)	0.082 (3)	0.075 (3)	0.003 (3)	−0.024 (2)	0.008 (3)
C10	0.083 (4)	0.092 (4)	0.055 (3)	0.003 (3)	−0.032 (3)	0.001 (3)
C11	0.111 (5)	0.086 (4)	0.047 (3)	−0.019 (4)	−0.007 (3)	0.014 (3)
C12	0.086 (3)	0.044 (2)	0.053 (2)	−0.009 (2)	−0.025 (3)	0.0027 (18)
C13	0.057 (2)	0.0449 (19)	0.046 (2)	−0.0006 (18)	−0.0149 (18)	0.0022 (17)
C14	0.055 (2)	0.0375 (18)	0.0337 (17)	0.0030 (17)	−0.0042 (16)	0.0017 (15)
C15	0.075 (3)	0.050 (2)	0.038 (2)	0.008 (2)	0.002 (2)	0.0029 (18)
C16	0.067 (3)	0.075 (3)	0.054 (3)	0.004 (3)	0.012 (2)	0.005 (2)
C17	0.065 (3)	0.077 (3)	0.067 (3)	−0.011 (3)	0.007 (2)	0.017 (3)
C18	0.083 (3)	0.059 (3)	0.066 (3)	−0.022 (3)	−0.007 (3)	−0.002 (2)
C19	0.075 (3)	0.052 (2)	0.073 (3)	−0.007 (2)	−0.004 (3)	−0.012 (2)
C20	0.068 (3)	0.044 (2)	0.052 (2)	0.001 (2)	0.001 (2)	−0.0080 (18)
C21	0.064 (3)	0.067 (3)	0.103 (4)	−0.006 (3)	0.016 (3)	−0.032 (3)
C22	0.056 (2)	0.068 (3)	0.086 (3)	−0.005 (3)	−0.003 (3)	−0.005 (3)
Cl	0.0732 (7)	0.0494 (6)	0.0825 (8)	−0.0190 (5)	0.0227 (7)	−0.0145 (6)

Zn—N4	2.134 (4)	C9—C10	1.530 (8)
Zn—N2	2.139 (4)	C9—H9A	0.9900
Zn—N3	2.235 (3)	C9—H9B	0.9900
Zn—N1	2.272 (4)	C10—C11	1.476 (9)
Zn—S	2.2804 (10)	C10—H10A	0.9900
S—C12	1.843 (4)	C10—H10B	0.9900
N1—C11	1.431 (8)	C11—H11A	0.9900
N1—C1	1.474 (7)	C11—H11B	0.9900
N1—H1C	0.9300	C12—C13	1.496 (6)
N2—C2	1.448 (8)	C12—H12A	0.9900
N2—C3	1.491 (8)	C12—H12B	0.9900
N2—H2C	0.9300	C13—C22	1.379 (7)
N3—C5	1.454 (7)	C13—C14	1.393 (6)
N3—C6	1.494 (7)	C14—C15	1.380 (6)
N3—H3C	0.9300	C14—C20	1.500 (6)
N4—C8	1.472 (6)	C15—C16	1.388 (7)
N4—C9	1.496 (6)	C15—H15A	0.9500
N4—H4C	0.9300	C16—C17	1.400 (8)
C1—C2	1.512 (10)	C16—H16A	0.9500
C1—H1A	0.9900	C17—C18	1.390 (8)
C1—H1B	0.9900	C17—H17A	0.9500
C2—H2A	0.9900	C18—C19	1.360 (8)
C2—H2B	0.9900	C18—H18A	0.9500
C3—C4	1.527 (10)	C19—C20	1.374 (7)
C3—H3A	0.9900	C19—H19A	0.9500
C3—H3B	0.9900	C20—C21	1.401 (8)
C4—C5	1.488 (10)	C21—C22	1.392 (7)
C4—H4A	0.9900	C21—H21A	0.9500
C4—H4B	0.9900	C22—H22A	0.9500
C5—H5A	0.9900	Cl—O43	1.31 (2)
C5—H5B	0.9900	Cl—O44	1.345 (12)
C6—C7	1.529 (8)	Cl—O41	1.373 (11)
C6—H6A	0.9900	Cl—O41A	1.39 (2)
C6—H6B	0.9900	Cl—O42	1.432 (12)
C7—C8	1.469 (8)	Cl—O42A	1.461 (11)
C7—H7A	0.9900	Cl—O44A	1.496 (15)
C7—H7B	0.9900	Cl—O43A	1.640 (16)
C8—H8A	0.9900	O43—O44	1.48 (3)
C8—H8B	0.9900
N4—Zn—N2	130.42 (16)	N4—C9—H9A	109.0
N4—Zn—N3	86.95 (15)	C10—C9—H9A	109.0
N2—Zn—N3	85.81 (17)	N4—C9—H9B	109.0
N4—Zn—N1	91.17 (15)	C10—C9—H9B	109.0
N2—Zn—N1	80.05 (17)	H9A—C9—H9B	107.8
N3—Zn—N1	159.70 (15)	C11—C10—C9	113.0 (5)
N4—Zn—S	118.88 (11)	C11—C10—H10A	109.0
N2—Zn—S	110.70 (12)	C9—C10—H10A	109.0
N3—Zn—S	99.13 (10)	C11—C10—H10B	109.0
N1—Zn—S	99.46 (11)	C9—C10—H10B	109.0
C12—S—Zn	101.15 (14)	H10A—C10—H10B	107.8
C11—N1—C1	112.6 (5)	N1—C11—C10	113.3 (4)
C11—N1—Zn	122.7 (3)	N1—C11—H11A	108.9
C1—N1—Zn	105.3 (3)	C10—C11—H11A	108.9
C11—N1—H1C	104.9	N1—C11—H11B	108.9
C1—N1—H1C	104.9	C10—C11—H11B	108.9
Zn—N1—H1C	104.9	H11A—C11—H11B	107.7
C2—N2—C3	112.8 (5)	C13—C12—S	111.1 (3)
C2—N2—Zn	109.4 (4)	C13—C12—H12A	109.4
C3—N2—Zn	114.3 (4)	S—C12—H12A	109.4
C2—N2—H2C	106.6	C13—C12—H12B	109.4
C3—N2—H2C	106.6	S—C12—H12B	109.4
Zn—N2—H2C	106.6	H12A—C12—H12B	108.0
C5—N3—C6	109.5 (4)	C22—C13—C14	108.2 (4)
C5—N3—Zn	110.9 (3)	C22—C13—C12	126.1 (4)
C6—N3—Zn	110.2 (3)	C14—C13—C12	125.7 (4)
C5—N3—H3C	108.7	C15—C14—C13	127.1 (4)
C6—N3—H3C	108.7	C15—C14—C20	125.4 (4)
Zn—N3—H3C	108.7	C13—C14—C20	107.4 (4)
C8—N4—C9	108.4 (4)	C14—C15—C16	129.4 (4)
C8—N4—Zn	112.4 (3)	C14—C15—H15A	115.3
C9—N4—Zn	117.4 (3)	C16—C15—H15A	115.3
C8—N4—H4C	105.9	C15—C16—C17	129.3 (5)
C9—N4—H4C	105.9	C15—C16—H16A	115.3
Zn—N4—H4C	105.9	C17—C16—H16A	115.3
N1—C1—C2	109.7 (4)	C18—C17—C16	128.6 (5)
N1—C1—H1A	109.7	C18—C17—H17A	115.7
C2—C1—H1A	109.7	C16—C17—H17A	115.7
N1—C1—H1B	109.7	C19—C18—C17	129.3 (5)
C2—C1—H1B	109.7	C19—C18—H18A	115.4
H1A—C1—H1B	108.2	C17—C18—H18A	115.4
N2—C2—C1	110.2 (5)	C18—C19—C20	129.2 (5)
N2—C2—H2A	109.6	C18—C19—H19A	115.4
C1—C2—H2A	109.6	C20—C19—H19A	115.4
N2—C2—H2B	109.6	C19—C20—C21	126.5 (5)
C1—C2—H2B	109.6	C19—C20—C14	128.7 (5)
H2A—C2—H2B	108.1	C21—C20—C14	104.8 (4)
N2—C3—C4	114.8 (5)	C22—C21—C20	109.2 (5)
N2—C3—H3A	108.6	C22—C21—H21A	125.4
C4—C3—H3A	108.6	C20—C21—H21A	125.4
N2—C3—H3B	108.6	C13—C22—C21	110.4 (5)
C4—C3—H3B	108.6	C13—C22—H22A	124.8
H3A—C3—H3B	107.5	C21—C22—H22A	124.8
C5—C4—C3	116.0 (5)	O43—Cl—O44	68.0 (13)
C5—C4—H4A	108.3	O43—Cl—O41	124.5 (12)
C3—C4—H4A	108.3	O44—Cl—O41	115.5 (7)
C5—C4—H4B	108.3	O43—Cl—O41A	119.0 (15)
C3—C4—H4B	108.3	O44—Cl—O41A	133.9 (10)
H4A—C4—H4B	107.4	O41—Cl—O41A	19.9 (9)
N3—C5—C4	112.5 (5)	O43—Cl—O42	93.4 (11)
N3—C5—H5A	109.1	O44—Cl—O42	116.7 (7)
C4—C5—H5A	109.1	O41—Cl—O42	123.9 (8)
N3—C5—H5B	109.1	O41A—Cl—O42	108.6 (11)
C4—C5—H5B	109.1	O43—Cl—O42A	120.1 (11)
H5A—C5—H5B	107.8	O44—Cl—O42A	129.2 (7)
N3—C6—C7	112.6 (4)	O41—Cl—O42A	100.0 (8)
N3—C6—H6A	109.1	O41A—Cl—O42A	89.0 (11)
C7—C6—H6A	109.1	O42—Cl—O42A	27.3 (6)
N3—C6—H6B	109.1	O43—Cl—O44A	116.3 (14)
C7—C6—H6B	109.1	O44—Cl—O44A	48.9 (6)
H6A—C6—H6B	107.8	O41—Cl—O44A	93.2 (8)
C8—C7—C6	115.5 (5)	O41A—Cl—O44A	111.1 (11)
C8—C7—H7A	108.4	O42—Cl—O44A	105.8 (7)
C6—C7—H7A	108.4	O42A—Cl—O44A	96.5 (7)
C8—C7—H7B	108.4	O43—Cl—O43A	42.8 (11)
C6—C7—H7B	108.4	O44—Cl—O43A	106.4 (8)
H7A—C7—H7B	107.5	O41—Cl—O43A	91.3 (8)
C7—C8—N4	113.7 (5)	O41A—Cl—O43A	78.9 (11)
C7—C8—H8A	108.8	O42—Cl—O43A	92.7 (7)
N4—C8—H8A	108.8	O42A—Cl—O43A	107.9 (7)
C7—C8—H8B	108.8	O44A—Cl—O43A	154.0 (8)
N4—C8—H8B	108.8	Cl—O43—O44	57.3 (11)
H8A—C8—H8B	107.7	Cl—O44—O43	54.7 (10)
N4—C9—C10	113.1 (5)

Zn—N4	2.134 (4)
Zn—N2	2.139 (4)
Zn—N3	2.235 (3)
Zn—N1	2.272 (4)
Zn—S	2.2804 (10)

N4—Zn—N2	130.42 (16)
N4—Zn—N3	86.95 (15)
N2—Zn—N3	85.81 (17)
N4—Zn—N1	91.17 (15)
N2—Zn—N1	80.05 (17)
N3—Zn—N1	159.70 (15)
N4—Zn—S	118.88 (11)
N2—Zn—S	110.70 (12)
N3—Zn—S	99.13 (10)
N1—Zn—S	99.46 (11)