Diammonium tetra-kis-(iso-thio-cyanato)-zincate-1,4,10,13,16-hexa-oxa-cyclo-octa-deca-ne-water (1/2/1).

The title compound, (NH4)2[Zn(NCS)4]·2C12H24O6·H2O, the result of the reaction of ammonium thio-cyanate, 18-crown-6 and zinc(II) chloride in aqueous solution, exhibits an unusual supra-molecular structure. The Zn atom, two of the thio-cyanate chains and a water mol-ecule, disordered over two positions, lie on a mirror plane. The macrocycle adopts a conformation with approximate D 3d symmetry. The ammonium mol-ecules are contained within the bowl of the macrocycle via extensive N-H⋯O hydrogen bonds and the complex mol-ecules are linked via N-H⋯S hydrogen bonds, forming chains along the c-axis direction. The macrocycle is disordered over two positions [refined occupancy ratio = 0.666 (8):0.334 (8)]. The S atoms of two iso-thio-cyanate ligands are disordered within and about the mirror plane.

Related literature

For background to crown ether/ammonium ion complexes, see: Fender et al. (2002 ▶); Kryatova et al. (2004 ▶); Akutagawa et al. (2002 ▶); Ramesh et al. (2012 ▶).

Experimental

Crystal data

(NH4)2[Zn(NCS)4]·2C12H24O6·H2O

M = 880.41

Orthorhombic,

a = 22.7875 (12) Å

b = 23.6254 (12) Å

c = 8.5593 (5) Å

V = 4608.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.802, T max = 0.861

24101 measured reflections

4641 independent reflections

2467 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.175

S = 1.00

4641 reflections

454 parameters

276 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019739/su2617sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019739/su2617Isup2.hkl

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

(NH4)2[Zn(NCS)4]·2C12H24O6·H2O	F(000) = 1864
Mr = 880.41	Dx = 1.269 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5119 reflections
a = 22.7875 (12) Å	θ = 2.6–26.7°
b = 23.6254 (12) Å	µ = 0.77 mm−1
c = 8.5593 (5) Å	T = 293 K
V = 4608.0 (4) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	2467 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω and φ scan	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −24→28
Tmin = 0.802, Tmax = 0.861	k = −19→29
24101 measured reflections	l = −10→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0932P)2 + 0.2607P] where P = (Fo2 + 2Fc2)/3
4641 reflections	(Δ/σ)max = 0.001
454 parameters	Δρmax = 0.72 e Å−3
276 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.51074 (15)	0.13492 (16)	0.9699 (5)	0.0534 (10)
C2	0.6728 (3)	0.2500	0.7518 (7)	0.0668 (16)
C3	0.4978 (4)	0.2500	0.4932 (11)	0.094 (2)
O1	0.6093 (3)	0.0412 (3)	0.5640 (8)	0.086 (2)	0.666 (8)
O2	0.6025 (4)	−0.0710 (3)	0.4650 (8)	0.082 (2)	0.666 (8)
O3	0.6681 (3)	−0.1007 (3)	0.1940 (9)	0.079 (2)	0.666 (8)
O4	0.6950 (3)	−0.0163 (3)	−0.0249 (8)	0.0798 (19)	0.666 (8)
O5	0.6998 (3)	0.0974 (4)	0.0798 (7)	0.083 (2)	0.666 (8)
O6	0.6318 (3)	0.1232 (3)	0.3415 (9)	0.092 (2)	0.666 (8)
C4	0.6209 (4)	0.1375 (4)	0.4993 (11)	0.103 (3)	0.666 (8)
H4A	0.6025	0.1744	0.5053	0.124*	0.666 (8)
H4B	0.6576	0.1388	0.5567	0.124*	0.666 (8)
C5	0.5811 (4)	0.0935 (4)	0.5696 (12)	0.106 (3)	0.666 (8)
H5A	0.5721	0.1034	0.6770	0.127*	0.666 (8)
H5B	0.5446	0.0918	0.5115	0.127*	0.666 (8)
C6	0.5761 (5)	0.0013 (5)	0.6449 (14)	0.097 (4)	0.666 (8)
H6A	0.5363	0.0007	0.6046	0.116*	0.666 (8)
H6B	0.5745	0.0110	0.7549	0.116*	0.666 (8)
C7	0.6040 (4)	−0.0556 (5)	0.6243 (9)	0.102 (3)	0.666 (8)
H7A	0.6443	−0.0544	0.6603	0.122*	0.666 (8)
H7B	0.5831	−0.0835	0.6859	0.122*	0.666 (8)
C8	0.6256 (5)	−0.1260 (4)	0.4391 (12)	0.103 (3)	0.666 (8)
H8A	0.6009	−0.1539	0.4898	0.123*	0.666 (8)
H8B	0.6646	−0.1286	0.4840	0.123*	0.666 (8)
C9	0.6284 (4)	−0.1378 (4)	0.2670 (12)	0.094 (3)	0.666 (8)
H9A	0.6407	−0.1766	0.2500	0.113*	0.666 (8)
H9B	0.5897	−0.1331	0.2214	0.113*	0.666 (8)
C10	0.6751 (5)	−0.1127 (5)	0.0337 (12)	0.093 (4)	0.666 (8)
H10A	0.6377	−0.1093	−0.0199	0.111*	0.666 (8)
H10B	0.6895	−0.1510	0.0198	0.111*	0.666 (8)
C11	0.7185 (4)	−0.0709 (4)	−0.0321 (10)	0.091 (3)	0.666 (8)
H11A	0.7547	−0.0724	0.0273	0.109*	0.666 (8)
H11B	0.7273	−0.0805	−0.1397	0.109*	0.666 (8)
C12	0.7343 (5)	0.0238 (5)	−0.0886 (15)	0.094 (4)	0.666 (8)
H12A	0.7426	0.0148	−0.1969	0.113*	0.666 (8)
H12B	0.7709	0.0237	−0.0308	0.113*	0.666 (8)
C13	0.7052 (4)	0.0806 (5)	−0.0767 (10)	0.098 (3)	0.666 (8)
H13A	0.7282	0.1084	−0.1333	0.118*	0.666 (8)
H13B	0.6666	0.0788	−0.1241	0.118*	0.666 (8)
C14	0.6687 (5)	0.1489 (5)	0.0924 (14)	0.107 (4)	0.666 (8)
H14A	0.6296	0.1447	0.0488	0.129*	0.666 (8)
H14B	0.6889	0.1785	0.0351	0.129*	0.666 (8)
C15	0.6647 (5)	0.1645 (4)	0.2617 (13)	0.107 (3)	0.666 (8)
H15A	0.7038	0.1669	0.3062	0.128*	0.666 (8)
H15B	0.6460	0.2012	0.2726	0.128*	0.666 (8)
O1'	0.6101 (6)	0.0748 (7)	0.5055 (18)	0.095 (4)	0.334 (8)
O2'	0.5880 (8)	−0.0418 (7)	0.489 (2)	0.094 (4)	0.334 (8)
O3'	0.6481 (6)	−0.1061 (6)	0.2641 (16)	0.073 (4)	0.334 (8)
O4'	0.6913 (5)	−0.0500 (6)	0.0013 (14)	0.062 (3)	0.334 (8)
O5'	0.7128 (6)	0.0659 (6)	0.0284 (19)	0.082 (4)	0.334 (8)
O6'	0.6437 (7)	0.1284 (6)	0.2342 (19)	0.103 (5)	0.334 (8)
C4'	0.6350 (10)	0.1591 (9)	0.373 (2)	0.115 (6)	0.334 (8)
H4'1	0.6223	0.1974	0.3495	0.138*	0.334 (8)
H4'2	0.6714	0.1613	0.4319	0.138*	0.334 (8)
C5'	0.5891 (10)	0.1293 (8)	0.468 (3)	0.118 (7)	0.334 (8)
H5'1	0.5809	0.1504	0.5623	0.142*	0.334 (8)
H5'2	0.5531	0.1263	0.4079	0.142*	0.334 (8)
C6'	0.5720 (9)	0.0449 (9)	0.604 (2)	0.103 (6)	0.334 (8)
H6'1	0.5334	0.0432	0.5563	0.124*	0.334 (8)
H6'2	0.5683	0.0649	0.7024	0.124*	0.334 (8)
C7'	0.5935 (12)	−0.0141 (10)	0.634 (2)	0.098 (7)	0.334 (8)
H7'1	0.6340	−0.0137	0.6686	0.118*	0.334 (8)
H7'2	0.5697	−0.0326	0.7132	0.118*	0.334 (8)
C8'	0.6053 (10)	−0.0980 (7)	0.513 (2)	0.094 (6)	0.334 (8)
H8'1	0.5787	−0.1159	0.5865	0.113*	0.334 (8)
H8'2	0.6444	−0.0987	0.5586	0.113*	0.334 (8)
C9'	0.6055 (9)	−0.1305 (8)	0.363 (2)	0.093 (6)	0.334 (8)
H9'1	0.6148	−0.1699	0.3822	0.112*	0.334 (8)
H9'2	0.5671	−0.1285	0.3139	0.112*	0.334 (8)
C10'	0.6499 (6)	−0.1330 (6)	0.1179 (19)	0.071 (4)	0.334 (8)
H10C	0.6134	−0.1267	0.0621	0.085*	0.334 (8)
H10D	0.6553	−0.1735	0.1312	0.085*	0.334 (8)
C11'	0.7003 (6)	−0.1085 (6)	0.028 (3)	0.058 (4)	0.334 (8)
H11C	0.7365	−0.1139	0.0858	0.070*	0.334 (8)
H11D	0.7041	−0.1279	−0.0716	0.070*	0.334 (8)
C12'	0.7390 (6)	−0.0224 (7)	−0.0687 (18)	0.080 (4)	0.334 (8)
H12C	0.7514	−0.0431	−0.1608	0.096*	0.334 (8)
H12D	0.7717	−0.0209	0.0038	0.096*	0.334 (8)
C13'	0.7211 (12)	0.0367 (9)	−0.114 (2)	0.082 (6)	0.334 (8)
H13C	0.7515	0.0547	−0.1755	0.098*	0.334 (8)
H13D	0.6850	0.0362	−0.1738	0.098*	0.334 (8)
C14'	0.6902 (10)	0.1195 (6)	−0.007 (3)	0.105 (6)	0.334 (8)
H14C	0.6521	0.1152	−0.0563	0.125*	0.334 (8)
H14D	0.7160	0.1382	−0.0809	0.125*	0.334 (8)
C15'	0.6838 (11)	0.1560 (10)	0.135 (3)	0.105 (7)	0.334 (8)
H15C	0.7213	0.1605	0.1871	0.127*	0.334 (8)
H15D	0.6692	0.1932	0.1067	0.127*	0.334 (8)
N1	0.52011 (15)	0.18067 (14)	0.9297 (4)	0.0703 (10)
N2	0.6247 (3)	0.2500	0.7865 (7)	0.0768 (16)
N3	0.5010 (3)	0.2500	0.6166 (7)	0.0796 (16)
N4	0.61488 (17)	0.01292 (18)	0.2144 (5)	0.0594 (9)
S1	0.49673 (5)	0.07035 (4)	1.02060 (15)	0.0704 (4)
S2	0.7443 (4)	0.2500	0.740 (7)	0.100 (6)	0.39 (9)
S2A	0.7397 (6)	0.2500	0.684 (5)	0.098 (5)	0.61 (9)
S3	0.5017 (4)	0.2703 (4)	0.3036 (5)	0.138 (3)	0.376 (9)
S3A	0.4660 (14)	0.2500	0.3119 (17)	0.161 (7)	0.248 (18)
Zn1	0.54016 (3)	0.2500	0.82110 (8)	0.0587 (3)
O1W	0.3179 (18)	0.2500	0.361 (5)	0.328 (15)	0.425 (15)
O2W	0.3443 (14)	0.2500	0.199 (3)	0.328 (15)	0.575 (15)
H1W	0.31 (2)	0.2500	0.258 (11)	0.492*	0.425 (15)
H2W	0.289 (15)	0.2500	0.43 (4)	0.492*	0.425 (15)
H3W	0.327 (15)	0.2500	0.29 (2)	0.492*	0.575 (15)
H4W	0.384 (3)	0.2500	0.19 (5)	0.492*	0.575 (15)
H4E	0.609 (2)	−0.0122 (17)	0.288 (4)	0.11 (2)*
H4F	0.5826 (12)	0.016 (2)	0.160 (5)	0.099 (18)*
H4G	0.6438 (14)	0.0081 (19)	0.148 (4)	0.097 (17)*
H4H	0.624 (2)	0.0393 (16)	0.282 (5)	0.11 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.048 (2)	0.053 (2)	0.059 (3)	0.0033 (18)	0.0027 (18)	0.004 (2)
C2	0.089 (5)	0.043 (3)	0.069 (4)	0.000	0.003 (4)	0.000
C3	0.110 (6)	0.090 (5)	0.083 (6)	0.000	−0.001 (5)	0.000
O1	0.080 (4)	0.112 (5)	0.067 (4)	0.007 (4)	0.016 (3)	−0.017 (4)
O2	0.097 (5)	0.083 (5)	0.065 (4)	−0.013 (4)	−0.009 (3)	0.026 (4)
O3	0.085 (5)	0.073 (4)	0.081 (5)	0.002 (3)	−0.018 (4)	−0.011 (4)
O4	0.061 (4)	0.113 (5)	0.065 (4)	0.007 (4)	0.013 (3)	−0.003 (4)
O5	0.082 (4)	0.087 (5)	0.080 (5)	−0.003 (4)	−0.014 (3)	0.031 (4)
O6	0.110 (4)	0.070 (4)	0.097 (6)	0.012 (3)	−0.008 (4)	−0.008 (4)
C4	0.108 (7)	0.098 (7)	0.102 (7)	0.038 (6)	−0.010 (6)	−0.047 (6)
C5	0.094 (6)	0.137 (8)	0.086 (7)	0.031 (7)	0.011 (5)	−0.042 (7)
C6	0.096 (8)	0.139 (10)	0.056 (6)	−0.014 (7)	0.023 (5)	−0.013 (6)
C7	0.114 (6)	0.133 (8)	0.059 (6)	−0.031 (6)	0.004 (5)	0.023 (6)
C8	0.120 (8)	0.084 (6)	0.105 (8)	−0.019 (6)	−0.026 (6)	0.030 (6)
C9	0.105 (7)	0.057 (5)	0.119 (9)	0.002 (5)	−0.032 (6)	−0.006 (6)
C10	0.092 (9)	0.089 (7)	0.097 (7)	0.030 (6)	−0.022 (7)	−0.033 (6)
C11	0.078 (6)	0.131 (9)	0.063 (5)	0.038 (7)	0.002 (5)	−0.034 (6)
C12	0.061 (6)	0.155 (10)	0.068 (7)	−0.007 (6)	0.017 (5)	0.000 (8)
C13	0.085 (6)	0.138 (9)	0.072 (6)	−0.023 (6)	0.007 (5)	0.022 (7)
C14	0.122 (7)	0.075 (7)	0.124 (9)	−0.010 (6)	−0.040 (7)	0.036 (7)
C15	0.129 (7)	0.058 (5)	0.133 (9)	0.009 (5)	−0.017 (7)	0.012 (6)
O1'	0.087 (7)	0.101 (10)	0.097 (10)	0.023 (8)	0.017 (7)	−0.039 (8)
O2'	0.098 (9)	0.108 (11)	0.075 (8)	−0.022 (8)	−0.004 (7)	0.019 (8)
O3'	0.072 (8)	0.053 (6)	0.094 (10)	−0.012 (6)	−0.007 (6)	0.004 (7)
O4'	0.047 (6)	0.076 (8)	0.063 (7)	0.009 (6)	0.018 (5)	−0.014 (7)
O5'	0.086 (8)	0.095 (9)	0.066 (8)	−0.023 (7)	−0.022 (7)	0.027 (8)
O6'	0.123 (10)	0.056 (7)	0.129 (14)	0.007 (6)	−0.046 (9)	−0.009 (8)
C4'	0.141 (13)	0.061 (10)	0.143 (16)	0.026 (10)	−0.024 (12)	−0.034 (11)
C5'	0.112 (12)	0.095 (11)	0.147 (15)	0.034 (11)	−0.015 (12)	−0.051 (11)
C6'	0.106 (12)	0.123 (14)	0.081 (11)	−0.001 (12)	0.026 (10)	−0.014 (11)
C7'	0.102 (13)	0.123 (14)	0.070 (12)	−0.014 (12)	0.020 (10)	0.002 (12)
C8'	0.104 (11)	0.094 (12)	0.084 (12)	−0.036 (10)	0.006 (10)	0.031 (10)
C9'	0.113 (12)	0.075 (10)	0.091 (13)	−0.040 (9)	−0.017 (10)	0.024 (10)
C10'	0.063 (8)	0.051 (7)	0.099 (11)	0.007 (6)	−0.011 (8)	−0.016 (8)
C11'	0.044 (9)	0.058 (8)	0.074 (9)	0.003 (7)	−0.007 (7)	−0.024 (7)
C12'	0.087 (10)	0.102 (11)	0.052 (9)	−0.019 (9)	0.017 (7)	−0.023 (9)
C13'	0.083 (12)	0.114 (13)	0.049 (10)	−0.023 (11)	0.004 (9)	0.022 (9)
C14'	0.124 (12)	0.084 (11)	0.106 (13)	−0.024 (10)	−0.035 (11)	0.035 (11)
C15'	0.140 (13)	0.057 (9)	0.120 (16)	−0.020 (10)	−0.046 (12)	0.011 (10)
N1	0.087 (2)	0.0477 (19)	0.076 (3)	−0.0038 (17)	0.0057 (19)	0.0091 (19)
N2	0.069 (3)	0.063 (3)	0.099 (5)	0.000	0.015 (3)	0.000
N3	0.110 (5)	0.068 (3)	0.060 (4)	0.000	0.009 (4)	0.000
N4	0.061 (3)	0.067 (2)	0.051 (3)	0.007 (2)	−0.001 (2)	−0.002 (2)
S1	0.0688 (7)	0.0521 (6)	0.0903 (9)	−0.0072 (5)	−0.0075 (6)	0.0253 (6)
S2	0.080 (5)	0.099 (5)	0.121 (17)	0.000	0.029 (5)	0.000
S2A	0.070 (3)	0.104 (3)	0.121 (12)	0.000	0.025 (4)	0.000
S3	0.149 (6)	0.198 (9)	0.067 (3)	−0.007 (4)	−0.005 (3)	0.016 (3)
S3A	0.234 (17)	0.175 (14)	0.076 (7)	0.000	0.019 (11)	0.000
Zn1	0.0725 (5)	0.0362 (3)	0.0674 (5)	0.000	0.0085 (4)	0.000
O1W	0.39 (3)	0.34 (2)	0.25 (3)	0.000	−0.20 (3)	0.000
O2W	0.39 (3)	0.34 (2)	0.25 (3)	0.000	−0.20 (3)	0.000

C1—N1	1.154 (4)	O2'—C7'	1.410 (10)
C1—S1	1.618 (4)	O3'—C10'	1.405 (10)
C2—N2	1.136 (7)	O3'—C9'	1.410 (10)
C2—S2A	1.631 (9)	O4'—C12'	1.403 (9)
C2—S2	1.632 (10)	O4'—C11'	1.414 (10)
C3—N3	1.058 (8)	O5'—C14'	1.403 (10)
C3—S3i	1.695 (10)	O5'—C13'	1.409 (10)
C3—S3	1.695 (10)	O6'—C15'	1.406 (10)
C3—S3A	1.714 (12)	O6'—C4'	1.409 (10)
O1—C6	1.393 (9)	C4'—C5'	1.497 (10)
O1—C5	1.394 (8)	C4'—H4'1	0.9700
O2—C7	1.411 (8)	C4'—H4'2	0.9700
O2—C8	1.420 (8)	C5'—H5'1	0.9700
O3—C9	1.406 (8)	C5'—H5'2	0.9700
O3—C10	1.410 (8)	C6'—C7'	1.501 (10)
O4—C11	1.398 (7)	C6'—H6'1	0.9700
O4—C12	1.411 (9)	C6'—H6'2	0.9700
O5—C13	1.402 (8)	C7'—H7'1	0.9700
O5—C14	1.413 (9)	C7'—H7'2	0.9700
O6—C15	1.407 (8)	C8'—C9'	1.500 (10)
O6—C4	1.414 (8)	C8'—H8'1	0.9700
C4—C5	1.504 (8)	C8'—H8'2	0.9700
C4—H4A	0.9700	C9'—H9'1	0.9700
C4—H4B	0.9700	C9'—H9'2	0.9700
C5—H5A	0.9700	C10'—C11'	1.500 (10)
C5—H5B	0.9700	C10'—H10C	0.9700
C6—C7	1.499 (9)	C10'—H10D	0.9700
C6—H6A	0.9700	C11'—H11C	0.9700
C6—H6B	0.9700	C11'—H11D	0.9700
C7—H7A	0.9700	C12'—C13'	1.506 (10)
C7—H7B	0.9700	C12'—H12C	0.9700
C8—C9	1.501 (8)	C12'—H12D	0.9700
C8—H8A	0.9700	C13'—H13C	0.9700
C8—H8B	0.9700	C13'—H13D	0.9700
C9—H9A	0.9700	C14'—C15'	1.499 (10)
C9—H9B	0.9700	C14'—H14C	0.9700
C10—C11	1.507 (8)	C14'—H14D	0.9700
C10—H10A	0.9700	C15'—H15C	0.9700
C10—H10B	0.9700	C15'—H15D	0.9700
C11—H11A	0.9700	N1—Zn1	1.938 (3)
C11—H11B	0.9700	N2—Zn1	1.948 (6)
C12—C13	1.501 (8)	N3—Zn1	1.964 (7)
C12—H12A	0.9700	N4—H4E	0.873 (10)
C12—H12B	0.9700	N4—H4F	0.874 (10)
C13—H13A	0.9700	N4—H4G	0.878 (10)
C13—H13B	0.9700	N4—H4H	0.878 (10)
C14—C15	1.497 (9)	S3—S3i	0.957 (17)
C14—H14A	0.9700	Zn1—N1i	1.938 (3)
C14—H14B	0.9700	O1W—H1W	0.900 (11)
C15—H15A	0.9700	O1W—H2W	0.899 (10)
C15—H15B	0.9700	O1W—H3W	0.61 (7)
O1'—C6'	1.401 (10)	O2W—H1W	0.9 (5)
O1'—C5'	1.411 (10)	O2W—H3W	0.900 (10)
O2'—C8'	1.401 (10)	O2W—H4W	0.898 (11)
N1—C1—S1	178.1 (4)	O6'—C4'—H4'1	110.1
N2—C2—S2A	174.3 (16)	C5'—C4'—H4'1	110.1
N2—C2—S2	168 (2)	O6'—C4'—H4'2	110.1
N3—C3—S3i	162.2 (5)	C5'—C4'—H4'2	110.1
N3—C3—S3	162.2 (5)	H4'1—C4'—H4'2	108.4
N3—C3—S3A	158.9 (13)	O1'—C5'—C4'	108.5 (17)
C6—O1—C5	109.4 (8)	O1'—C5'—H5'1	110.0
C7—O2—C8	112.2 (8)	C4'—C5'—H5'1	110.0
C9—O3—C10	112.3 (7)	O1'—C5'—H5'2	110.0
C11—O4—C12	111.0 (8)	C4'—C5'—H5'2	110.0
C13—O5—C14	111.2 (9)	H5'1—C5'—H5'2	108.4
C15—O6—C4	113.1 (9)	O1'—C6'—C7'	112 (2)
O6—C4—C5	108.9 (7)	O1'—C6'—H6'1	109.3
O6—C4—H4A	109.9	C7'—C6'—H6'1	109.3
C5—C4—H4A	109.9	O1'—C6'—H6'2	109.3
O6—C4—H4B	109.9	C7'—C6'—H6'2	109.3
C5—C4—H4B	109.9	H6'1—C6'—H6'2	108.0
H4A—C4—H4B	108.3	O2'—C7'—C6'	104.5 (18)
O1—C5—C4	108.7 (9)	O2'—C7'—H7'1	110.8
O1—C5—H5A	110.0	C6'—C7'—H7'1	110.8
C4—C5—H5A	110.0	O2'—C7'—H7'2	110.8
O1—C5—H5B	110.0	C6'—C7'—H7'2	110.8
C4—C5—H5B	110.0	H7'1—C7'—H7'2	108.9
H5A—C5—H5B	108.3	O2'—C8'—C9'	110.9 (17)
O1—C6—C7	108.6 (8)	O2'—C8'—H8'1	109.5
O1—C6—H6A	110.0	C9'—C8'—H8'1	109.5
C7—C6—H6A	110.0	O2'—C8'—H8'2	109.5
O1—C6—H6B	110.0	C9'—C8'—H8'2	109.5
C7—C6—H6B	110.0	H8'1—C8'—H8'2	108.0
H6A—C6—H6B	108.4	O3'—C9'—C8'	107.9 (14)
O2—C7—C6	109.5 (9)	O3'—C9'—H9'1	110.1
O2—C7—H7A	109.8	C8'—C9'—H9'1	110.1
C6—C7—H7A	109.8	O3'—C9'—H9'2	110.1
O2—C7—H7B	109.8	C8'—C9'—H9'2	110.1
C6—C7—H7B	109.8	H9'1—C9'—H9'2	108.4
H7A—C7—H7B	108.2	O3'—C10'—C11'	107.8 (15)
O2—C8—C9	109.8 (7)	O3'—C10'—H10C	110.1
O2—C8—H8A	109.7	C11'—C10'—H10C	110.1
C9—C8—H8A	109.7	O3'—C10'—H10D	110.1
O2—C8—H8B	109.7	C11'—C10'—H10D	110.1
C9—C8—H8B	109.7	H10C—C10'—H10D	108.5
H8A—C8—H8B	108.2	O4'—C11'—C10'	110.3 (12)
O3—C9—C8	110.4 (8)	O4'—C11'—H11C	109.6
O3—C9—H9A	109.6	C10'—C11'—H11C	109.6
C8—C9—H9A	109.6	O4'—C11'—H11D	109.6
O3—C9—H9B	109.6	C10'—C11'—H11D	109.6
C8—C9—H9B	109.6	H11C—C11'—H11D	108.1
H9A—C9—H9B	108.1	O4'—C12'—C13'	109.3 (18)
O3—C10—C11	107.8 (8)	O4'—C12'—H12C	109.8
O3—C10—H10A	110.2	C13'—C12'—H12C	109.8
C11—C10—H10A	110.2	O4'—C12'—H12D	109.8
O3—C10—H10B	110.2	C13'—C12'—H12D	109.8
C11—C10—H10B	110.2	H12C—C12'—H12D	108.3
H10A—C10—H10B	108.5	O5'—C13'—C12'	105.6 (15)
O4—C11—C10	109.8 (9)	O5'—C13'—H13C	110.6
O4—C11—H11A	109.7	C12'—C13'—H13C	110.6
C10—C11—H11A	109.7	O5'—C13'—H13D	110.6
O4—C11—H11B	109.7	C12'—C13'—H13D	110.6
C10—C11—H11B	109.7	H13C—C13'—H13D	108.8
H11A—C11—H11B	108.2	O5'—C14'—C15'	112 (2)
O4—C12—C13	107.1 (9)	O5'—C14'—H14C	109.1
O4—C12—H12A	110.3	C15'—C14'—H14C	109.1
C13—C12—H12A	110.3	O5'—C14'—H14D	109.1
O4—C12—H12B	110.3	C15'—C14'—H14D	109.1
C13—C12—H12B	110.3	H14C—C14'—H14D	107.9
H12A—C12—H12B	108.6	O6'—C15'—C14'	106.6 (19)
O5—C13—C12	110.9 (11)	O6'—C15'—H15C	110.4
O5—C13—H13A	109.5	C14'—C15'—H15C	110.4
C12—C13—H13A	109.5	O6'—C15'—H15D	110.4
O5—C13—H13B	109.5	C14'—C15'—H15D	110.4
C12—C13—H13B	109.5	H15C—C15'—H15D	108.6
H13A—C13—H13B	108.0	C1—N1—Zn1	168.0 (4)
O5—C14—C15	108.4 (9)	C2—N2—Zn1	173.6 (6)
O5—C14—H14A	110.0	C3—N3—Zn1	157.0 (7)
C15—C14—H14A	110.0	H4E—N4—H4F	109 (5)
O5—C14—H14B	110.0	H4E—N4—H4G	119 (5)
C15—C14—H14B	110.0	H4F—N4—H4G	107 (5)
H14A—C14—H14B	108.4	H4E—N4—H4H	92 (5)
O6—C15—C14	109.4 (11)	H4F—N4—H4H	120 (5)
O6—C15—H15A	109.8	H4G—N4—H4H	110 (5)
C14—C15—H15A	109.8	S3i—S3—C3	73.6 (3)
O6—C15—H15B	109.8	N1—Zn1—N1i	115.4 (2)
C14—C15—H15B	109.8	N1—Zn1—N2	107.82 (13)
H15A—C15—H15B	108.2	N1i—Zn1—N2	107.82 (13)
C6'—O1'—C5'	112.8 (17)	N1—Zn1—N3	108.70 (13)
C8'—O2'—C7'	106.5 (15)	N1i—Zn1—N3	108.70 (13)
C10'—O3'—C9'	111.7 (14)	N2—Zn1—N3	108.2 (2)
C12'—O4'—C11'	114.2 (14)	H1W—O1W—H2W	120 (2)
C14'—O5'—C13'	107.7 (17)	H2W—O1W—H3W	152 (10)
C15'—O6'—C4'	111.2 (18)	H1W—O2W—H4W	152 (10)
O6'—C4'—C5'	108 (2)	H3W—O2W—H4W	121 (2)
C15—O6—C4—C5	174.9 (8)	O1'—C6'—C7'—O2'	−68 (3)
C6—O1—C5—C4	173.1 (8)	C7'—O2'—C8'—C9'	−175.8 (18)
O6—C4—C5—O1	61.5 (10)	C10'—O3'—C9'—C8'	−178.1 (15)
C5—O1—C6—C7	174.5 (8)	O2'—C8'—C9'—O3'	64 (2)
C8—O2—C7—C6	−176.9 (8)	C9'—O3'—C10'—C11'	−174.2 (15)
O1—C6—C7—O2	−63.5 (11)	C12'—O4'—C11'—C10'	174.0 (14)
C7—O2—C8—C9	−174.4 (8)	O3'—C10'—C11'—O4'	−62.7 (18)
C10—O3—C9—C8	176.1 (8)	C11'—O4'—C12'—C13'	171.2 (15)
O2—C8—C9—O3	64.5 (10)	C14'—O5'—C13'—C12'	−174.0 (16)
C9—O3—C10—C11	−179.8 (8)	O4'—C12'—C13'—O5'	68 (2)
C12—O4—C11—C10	−178.8 (9)	C13'—O5'—C14'—C15'	−175.8 (19)
O3—C10—C11—O4	−65.3 (10)	C4'—O6'—C15'—C14'	179.3 (18)
C11—O4—C12—C13	179.6 (8)	O5'—C14'—C15'—O6'	−62 (2)
C14—O5—C13—C12	−175.7 (9)	S3i—C3—N3—Zn1	67 (3)
O4—C12—C13—O5	67.7 (11)	S3—C3—N3—Zn1	−67 (3)
C13—O5—C14—C15	−179.8 (8)	S3A—C3—N3—Zn1	180.0
C4—O6—C15—C14	−174.1 (8)	N3—C3—S3—S3i	156 (3)
O5—C14—C15—O6	−63.7 (11)	S3A—C3—S3—S3i	−62.2 (12)
C15'—O6'—C4'—C5'	176.4 (18)	C1—N1—Zn1—N1i	170.5 (15)
C6'—O1'—C5'—C4'	175.5 (17)	C1—N1—Zn1—N2	−69.0 (17)
O6'—C4'—C5'—O1'	62 (2)	C1—N1—Zn1—N3	48.1 (17)
C5'—O1'—C6'—C7'	176.4 (18)	C3—N3—Zn1—N1	−116.85 (12)
C8'—O2'—C7'—C6'	−177.5 (18)	C3—N3—Zn1—N1i	116.85 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4H···O1	0.88 (1)	2.44 (4)	3.069 (8)	129 (4)
N4—H4E···O2	0.87 (1)	2.06 (1)	2.934 (8)	176 (5)
N4—H4G···O4	0.88 (1)	1.97 (2)	2.829 (7)	166 (4)
N4—H4G···O5	0.88 (1)	2.53 (4)	3.010 (8)	115 (3)
N4—H4H···O6	0.88 (1)	2.05 (3)	2.850 (8)	150 (5)
N4—H4F···S1ii	0.87 (1)	2.63 (2)	3.441 (4)	156 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4H⋯O1	0.88 (1)	2.44 (4)	3.069 (8)	129 (4)
N4—H4E⋯O2	0.87 (1)	2.06 (1)	2.934 (8)	176 (5)
N4—H4G⋯O4	0.88 (1)	1.97 (2)	2.829 (7)	166 (4)
N4—H4G⋯O5	0.88 (1)	2.53 (4)	3.010 (8)	115 (3)
N4—H4H⋯O6	0.88 (1)	2.05 (3)	2.850 (8)	150 (5)
N4—H4F⋯S1i	0.87 (1)	2.63 (2)	3.441 (4)	156 (4)

Symmetry code: (i) .