Bis(1,10-phenanthroline-κ(2) N,N')(sulfato-κO)zinc(II) propane-1,2-diol monosolvate.

In the title compound, [Zn(SO4)(C12H8N2)2]·C3H8O2, the Zn(II) ion is in a distorted square-pyramidal coordination environment composed of four N atoms from two chelating 1,10-phenanthroline ligands and one O atom from a monodentate sulfate ligand. The Zn(II) ion lies on a twofold rotation axis. The sulfate ligand and propane-1,2-diol mol-ecules are disordered across the twofold rotation axis. The dihedral angle between the two chelating N2C2 groups is 83.26 (13)°. In the crystal, the complex mol-ecule and the propane-1,2-diol mol-ecule are connected through a pair of O-H⋯O hydrogen bonds.

Related literature

For the ethane-1,2-diol solvate of the title complex, see: Zhu et al. (2006 ▶) and for the propane-1,3-diol solvate of the title complex, see: Cui et al. (2010 ▶). For related structures and background references, see: Batten & Robson (1998 ▶); Zhang et al. (2010 ▶); Zhong (2010 ▶); Zhong et al. (2011 ▶).

Experimental

Crystal data

[Zn(SO4)(C12H8N2)2]·C3H8O2

M = 597.93

Monoclinic,

a = 17.3913 (10) Å

b = 12.9247 (7) Å

c = 13.2214 (7) Å

β = 123.248 (5)°

V = 2485.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.13 mm−1

T = 223 K

0.35 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.968, T max = 1.000

5735 measured reflections

2191 independent reflections

1878 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.06

2191 reflections

186 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302610X/lh5651sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302610X/lh5651Isup2.hkl

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

[Zn(SO4)(C12H8N2)2]·C3H8O2	F(000) = 1232
Mr = 597.93	Dx = 1.598 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2296 reflections
a = 17.3913 (10) Å	θ = 3.5–28.8°
b = 12.9247 (7) Å	µ = 1.13 mm−1
c = 13.2214 (7) Å	T = 223 K
β = 123.248 (5)°	Block, colourless
V = 2485.4 (2) Å3	0.35 × 0.20 × 0.15 mm
Z = 4

Rigaku Mercury CCD diffractometer	2191 independent reflections
Radiation source: fine-focus sealed tube	1878 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.035
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.8°
ω scans	h = −20→20
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −15→14
Tmin = 0.968, Tmax = 1.000	l = −14→15
5735 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0486P)2 + 2.9011P] where P = (Fo2 + 2Fc2)/3
2191 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.73 e Å−3
4 restraints	Δρmin = −0.54 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)
Zn1	0.0000	0.30049 (4)	0.2500	0.02159 (19)
S1	0.0034 (2)	0.54103 (11)	0.2316 (3)	0.0167 (6)	0.50
O1	0.0136 (3)	0.4449 (3)	0.3022 (4)	0.0257 (5)	0.50
O2	−0.0007 (3)	0.5122 (3)	0.1220 (4)	0.0257 (5)	0.50
O3	0.0811 (6)	0.6077 (9)	0.3077 (9)	0.0257 (5)	0.50
O4	−0.0835 (7)	0.5935 (8)	0.1998 (10)	0.0257 (5)	0.50
O5	0.0562 (14)	0.7871 (13)	0.1824 (16)	0.046 (2)	0.50
H5	0.0423	0.7309	0.1988	0.069*	0.50
O6	−0.0460 (14)	0.7974 (14)	0.3059 (16)	0.046 (2)	0.50
H6	−0.0423	0.7429	0.2756	0.069*	0.50
N1	0.09382 (15)	0.27777 (19)	0.1947 (2)	0.0222 (6)
N2	0.10269 (16)	0.2072 (2)	0.3926 (2)	0.0228 (6)
C1	0.0913 (2)	0.3167 (2)	0.1003 (3)	0.0261 (7)
H1A	0.0459	0.3660	0.0520	0.031*
C2	0.1535 (2)	0.2875 (3)	0.0694 (3)	0.0284 (7)
H2A	0.1497	0.3170	0.0018	0.034*
C3	0.2194 (2)	0.2159 (3)	0.1382 (3)	0.0297 (8)
H3A	0.2607	0.1947	0.1173	0.036*
C4	0.2257 (2)	0.1735 (2)	0.2406 (3)	0.0248 (7)
C5	0.2950 (2)	0.1021 (3)	0.3207 (3)	0.0284 (7)
H5A	0.3380	0.0786	0.3038	0.034*
C6	0.3001 (2)	0.0674 (3)	0.4204 (3)	0.0293 (8)
H6A	0.3465	0.0202	0.4719	0.035*
C7	0.2354 (2)	0.1019 (2)	0.4489 (3)	0.0242 (7)
C8	0.2402 (2)	0.0709 (3)	0.5542 (3)	0.0303 (8)
H8A	0.2858	0.0244	0.6088	0.036*
C9	0.1776 (2)	0.1094 (3)	0.5760 (3)	0.0338 (8)
H9A	0.1805	0.0906	0.6466	0.041*
C10	0.1096 (2)	0.1765 (3)	0.4932 (3)	0.0297 (8)
H10A	0.0665	0.2014	0.5091	0.036*
C11	0.16579 (19)	0.1707 (2)	0.3712 (3)	0.0219 (7)
C12	0.16033 (19)	0.2076 (2)	0.2646 (3)	0.0209 (7)
C13	0.0615 (9)	0.8631 (8)	0.2607 (13)	0.082 (2)	0.50
H13A	0.0782	0.9287	0.2404	0.098*	0.50
H13B	0.1113	0.8448	0.3432	0.098*	0.50
C14	−0.0247 (9)	0.8802 (6)	0.2597 (14)	0.082 (2)	0.50
H14A	−0.0759	0.8875	0.1739	0.098*	0.50
C15	−0.0222 (8)	0.9778 (6)	0.3227 (11)	0.082 (2)	0.50
H15A	−0.0019	1.0347	0.2950	0.123*	0.50
H15B	0.0202	0.9693	0.4093	0.123*	0.50
H15C	−0.0832	0.9925	0.3046	0.123*	0.50

	U11	U22	U33	U12	U13	U23
Zn1	0.0229 (3)	0.0194 (3)	0.0300 (3)	0.000	0.0193 (2)	0.000
S1	0.0167 (8)	0.0184 (7)	0.0179 (19)	−0.0003 (7)	0.0114 (10)	0.0012 (7)
O1	0.0256 (9)	0.0259 (17)	0.0295 (12)	0.0019 (12)	0.0175 (9)	0.0001 (12)
O2	0.0256 (9)	0.0259 (17)	0.0295 (12)	0.0019 (12)	0.0175 (9)	0.0001 (12)
O3	0.0256 (9)	0.0259 (17)	0.0295 (12)	0.0019 (12)	0.0175 (9)	0.0001 (12)
O4	0.0256 (9)	0.0259 (17)	0.0295 (12)	0.0019 (12)	0.0175 (9)	0.0001 (12)
O5	0.077 (4)	0.033 (3)	0.070 (3)	−0.001 (3)	0.067 (3)	−0.004 (3)
O6	0.077 (4)	0.033 (3)	0.070 (3)	−0.001 (3)	0.067 (3)	−0.004 (3)
N1	0.0208 (12)	0.0242 (14)	0.0252 (14)	0.0010 (11)	0.0150 (11)	0.0031 (11)
N2	0.0233 (13)	0.0260 (15)	0.0242 (14)	−0.0001 (11)	0.0162 (11)	−0.0012 (11)
C1	0.0269 (16)	0.0261 (18)	0.0290 (18)	0.0022 (14)	0.0176 (14)	0.0056 (14)
C2	0.0328 (17)	0.034 (2)	0.0276 (18)	0.0024 (15)	0.0223 (15)	0.0040 (15)
C3	0.0285 (17)	0.036 (2)	0.0334 (19)	0.0027 (15)	0.0226 (15)	−0.0001 (15)
C4	0.0247 (15)	0.0268 (18)	0.0260 (17)	0.0018 (13)	0.0159 (14)	−0.0026 (14)
C5	0.0256 (15)	0.0322 (19)	0.0317 (19)	0.0062 (14)	0.0183 (14)	−0.0049 (15)
C6	0.0281 (16)	0.0296 (19)	0.0315 (19)	0.0078 (14)	0.0171 (15)	0.0004 (14)
C7	0.0252 (15)	0.0253 (17)	0.0220 (16)	−0.0016 (13)	0.0129 (13)	−0.0025 (13)
C8	0.0309 (17)	0.031 (2)	0.0263 (18)	0.0050 (14)	0.0140 (15)	0.0049 (14)
C9	0.0384 (18)	0.044 (2)	0.0231 (18)	0.0017 (17)	0.0198 (16)	0.0039 (16)
C10	0.0302 (16)	0.038 (2)	0.0285 (19)	0.0045 (15)	0.0208 (15)	0.0007 (15)
C11	0.0248 (15)	0.0199 (16)	0.0251 (17)	−0.0014 (13)	0.0163 (14)	−0.0029 (13)
C12	0.0198 (14)	0.0196 (16)	0.0259 (17)	−0.0012 (13)	0.0141 (13)	−0.0024 (13)
C13	0.134 (8)	0.031 (3)	0.146 (6)	−0.012 (3)	0.119 (6)	−0.008 (4)
C14	0.134 (8)	0.031 (3)	0.146 (6)	−0.012 (3)	0.119 (6)	−0.008 (4)
C15	0.134 (8)	0.031 (3)	0.146 (6)	−0.012 (3)	0.119 (6)	−0.008 (4)

Zn1—O1	1.959 (4)	N2—C11	1.358 (4)
Zn1—O1i	1.959 (4)	C1—C2	1.402 (4)
Zn1—N2i	2.123 (3)	C1—H1A	0.9400
Zn1—N2	2.123 (3)	C2—C3	1.362 (5)
Zn1—N1	2.142 (2)	C2—H2A	0.9400
Zn1—N1i	2.142 (2)	C3—C4	1.408 (4)
S1—O1i	1.298 (5)	C3—H3A	0.9400
S1—O4i	1.355 (11)	C4—C12	1.408 (4)
S1—O3	1.446 (11)	C4—C5	1.424 (4)
S1—O2	1.459 (4)	C5—C6	1.348 (5)
S1—O4	1.492 (12)	C5—H5A	0.9400
S1—O1	1.505 (4)	C6—C7	1.440 (4)
S1—O3i	1.529 (12)	C6—H6A	0.9400
S1—O2i	1.998 (4)	C7—C11	1.396 (4)
O1—S1i	1.298 (4)	C7—C8	1.407 (4)
O1—O2i	1.435 (6)	C8—C9	1.362 (4)
O2—O1i	1.435 (6)	C8—H8A	0.9400
O2—S1i	1.998 (4)	C9—C10	1.389 (5)
O3—O4i	0.223 (14)	C9—H9A	0.9400
O3—S1i	1.529 (12)	C10—H10A	0.9400
O4—O3i	0.223 (14)	C11—C12	1.441 (4)
O4—S1i	1.355 (11)	C13—C14	1.508 (8)
O5—C13	1.394 (9)	C13—H13A	0.9800
O5—H5	0.8300	C13—H13B	0.9800
O6—C14	1.380 (8)	C14—C15	1.499 (9)
O6—H6	0.8300	C14—H14A	0.9900
N1—C1	1.324 (4)	C15—H15A	0.9700
N1—C12	1.357 (4)	C15—H15B	0.9700
N2—C10	1.329 (4)	C15—H15C	0.9700
O1—Zn1—N2i	137.27 (13)	C10—N2—C11	117.7 (3)
O1i—Zn1—N2i	110.38 (13)	C10—N2—Zn1	129.0 (2)
O1—Zn1—N2	110.38 (13)	C11—N2—Zn1	113.3 (2)
O1i—Zn1—N2	137.27 (13)	N1—C1—C2	122.7 (3)
N2i—Zn1—N2	110.75 (14)	N1—C1—H1A	118.6
O1—Zn1—N1	106.45 (13)	C2—C1—H1A	118.6
O1i—Zn1—N1	88.75 (13)	C3—C2—C1	119.3 (3)
N2i—Zn1—N1	92.67 (9)	C3—C2—H2A	120.3
N2—Zn1—N1	78.32 (9)	C1—C2—H2A	120.3
O1—Zn1—N1i	88.75 (13)	C2—C3—C4	120.0 (3)
O1i—Zn1—N1i	106.45 (13)	C2—C3—H3A	120.0
N2i—Zn1—N1i	78.32 (9)	C4—C3—H3A	120.0
N2—Zn1—N1i	92.67 (9)	C3—C4—C12	116.6 (3)
N1—Zn1—N1i	164.24 (14)	C3—C4—C5	123.7 (3)
O1i—S1—O4i	131.8 (5)	C12—C4—C5	119.6 (3)
O1i—S1—O3	139.5 (5)	C6—C5—C4	121.2 (3)
O4i—S1—O2	105.4 (5)	C6—C5—H5A	119.4
O3—S1—O2	111.2 (5)	C4—C5—H5A	119.4
O1i—S1—O4	109.5 (5)	C5—C6—C7	120.7 (3)
O4i—S1—O4	118.1 (7)	C5—C6—H6A	119.6
O3—S1—O4	109.9 (3)	C7—C6—H6A	119.6
O2—S1—O4	110.2 (5)	C11—C7—C8	117.8 (3)
O4i—S1—O1	105.6 (6)	C11—C7—C6	119.5 (3)
O3—S1—O1	108.2 (6)	C8—C7—C6	122.7 (3)
O2—S1—O1	109.3 (2)	C9—C8—C7	119.0 (3)
O4—S1—O1	107.9 (3)	C9—C8—H8A	120.5
O1i—S1—O3i	115.3 (5)	C7—C8—H8A	120.5
O4i—S1—O3i	112.9 (3)	C8—C9—C10	119.7 (3)
O3—S1—O3i	104.9 (7)	C8—C9—H9A	120.2
O2—S1—O3i	107.0 (5)	C10—C9—H9A	120.2
O1—S1—O3i	116.1 (3)	N2—C10—C9	123.1 (3)
O1i—S1—O2i	91.9 (2)	N2—C10—H10A	118.5
O4i—S1—O2i	90.3 (5)	C9—C10—H10A	118.5
O3—S1—O2i	86.9 (5)	N2—C11—C7	122.8 (3)
O2—S1—O2i	154.2 (3)	N2—C11—C12	117.5 (3)
O4—S1—O2i	78.4 (4)	C7—C11—C12	119.7 (3)
O3i—S1—O2i	84.5 (4)	N1—C12—C4	123.3 (3)
O1i—O1—S1i	74.3 (2)	N1—C12—C11	117.4 (2)
O1i—O1—O2i	134.1 (3)	C4—C12—C11	119.2 (3)
S1i—O1—O2i	64.3 (3)	O5—C13—C14	115.9 (14)
O1i—O1—S1	56.15 (18)	O5—C13—H13A	108.3
O2i—O1—S1	85.6 (3)	C14—C13—H13A	108.3
O1i—O1—Zn1	72.35 (12)	O5—C13—H13B	108.3
S1i—O1—Zn1	146.1 (3)	C14—C13—H13B	108.3
O2i—O1—Zn1	142.0 (3)	H13A—C13—H13B	107.4
S1—O1—Zn1	128.1 (2)	O6—C14—C15	109.9 (13)
O1i—O2—S1	53.3 (2)	O6—C14—C13	112.9 (16)
O1i—O2—S1i	48.7 (2)	C15—C14—C13	113.1 (8)
O4i—O3—S1	62 (5)	O6—C14—H14A	106.9
O4i—O3—S1i	76 (6)	C15—C14—H14A	106.9
O3i—O4—S1i	110 (5)	C13—C14—H14A	106.9
O3i—O4—S1	95 (6)	C14—C15—H15A	109.5
C13—O5—H5	109.5	C14—C15—H15B	109.5
C14—O6—H6	109.5	H15A—C15—H15B	109.5
C1—N1—C12	118.1 (2)	C14—C15—H15C	109.5
C1—N1—Zn1	129.2 (2)	H15A—C15—H15C	109.5
C12—N1—Zn1	112.58 (19)	H15B—C15—H15C	109.5
S1i—S1—O1—O1i	144.5 (10)	O2i—S1—O3—S1i	−14.0 (4)
O4i—S1—O1—O1i	−132.2 (5)	S1i—S1—O4—O3i	132 (6)
O3—S1—O1—O1i	−140.5 (5)	O1i—S1—O4—O3i	−135 (6)
O2—S1—O1—O1i	−19.2 (4)	O4i—S1—O4—O3i	53 (6)
O4—S1—O1—O1i	100.7 (6)	O3—S1—O4—O3i	54 (7)
O3i—S1—O1—O1i	101.9 (7)	O2—S1—O4—O3i	−69 (6)
O2i—S1—O1—O1i	153.1 (5)	O1—S1—O4—O3i	172 (6)
O1i—S1—O1—S1i	−144.5 (10)	O2i—S1—O4—O3i	137 (6)
O4i—S1—O1—S1i	83.3 (9)	O1i—S1—O4—S1i	92.8 (5)
O3—S1—O1—S1i	75.1 (8)	O4i—S1—O4—S1i	−79.2 (8)
O2—S1—O1—S1i	−163.7 (10)	O3—S1—O4—S1i	−77.5 (7)
O4—S1—O1—S1i	−43.8 (8)	O2—S1—O4—S1i	159.6 (5)
O3i—S1—O1—S1i	−42.6 (8)	O1—S1—O4—S1i	40.3 (5)
O2i—S1—O1—S1i	8.7 (8)	O3i—S1—O4—S1i	−132 (6)
S1i—S1—O1—O2i	−8.7 (8)	O2i—S1—O4—S1i	4.9 (4)
O1i—S1—O1—O2i	−153.1 (5)	O1—Zn1—N1—C1	−68.4 (3)
O4i—S1—O1—O2i	74.7 (4)	O1i—Zn1—N1—C1	−37.4 (3)
O3—S1—O1—O2i	66.4 (4)	N2i—Zn1—N1—C1	72.9 (3)
O2—S1—O1—O2i	−172.3 (2)	N2—Zn1—N1—C1	−176.4 (3)
O4—S1—O1—O2i	−52.5 (6)	N1i—Zn1—N1—C1	127.4 (3)
O3i—S1—O1—O2i	−51.2 (6)	O1—Zn1—N1—C12	116.5 (2)
S1i—S1—O1—Zn1	152.2 (8)	O1i—Zn1—N1—C12	147.5 (2)
O1i—S1—O1—Zn1	7.8 (2)	N2i—Zn1—N1—C12	−102.2 (2)
O4i—S1—O1—Zn1	−124.4 (4)	N2—Zn1—N1—C12	8.5 (2)
O3—S1—O1—Zn1	−132.7 (4)	N1i—Zn1—N1—C12	−47.68 (19)
O2—S1—O1—Zn1	−11.4 (5)	O1—Zn1—N2—C10	72.9 (3)
O4—S1—O1—Zn1	108.4 (6)	O1i—Zn1—N2—C10	101.2 (3)
O3i—S1—O1—Zn1	109.7 (6)	N2i—Zn1—N2—C10	−95.3 (3)
O2i—S1—O1—Zn1	160.9 (4)	N1—Zn1—N2—C10	176.3 (3)
N2i—Zn1—O1—O1i	−50.2 (4)	N1i—Zn1—N2—C10	−16.8 (3)
N2—Zn1—O1—O1i	146.2 (3)	O1—Zn1—N2—C11	−111.1 (2)
N1—Zn1—O1—O1i	62.8 (4)	O1i—Zn1—N2—C11	−82.9 (3)
N1i—Zn1—O1—O1i	−121.4 (4)	N2i—Zn1—N2—C11	80.7 (2)
O1i—Zn1—O1—S1i	11.1 (3)	N1—Zn1—N2—C11	−7.7 (2)
N2i—Zn1—O1—S1i	−39.1 (6)	N1i—Zn1—N2—C11	159.2 (2)
N2—Zn1—O1—S1i	157.3 (5)	C12—N1—C1—C2	0.8 (5)
N1—Zn1—O1—S1i	73.9 (5)	Zn1—N1—C1—C2	−174.1 (2)
N1i—Zn1—O1—S1i	−110.3 (5)	N1—C1—C2—C3	0.3 (5)
O1i—Zn1—O1—O2i	141.2 (8)	C1—C2—C3—C4	−1.3 (5)
N2i—Zn1—O1—O2i	91.0 (5)	C2—C3—C4—C12	1.2 (5)
N2—Zn1—O1—O2i	−72.6 (5)	C2—C3—C4—C5	−176.9 (3)
N1—Zn1—O1—O2i	−155.9 (5)	C3—C4—C5—C6	177.1 (3)
N1i—Zn1—O1—O2i	19.8 (5)	C12—C4—C5—C6	−1.0 (5)
O1i—Zn1—O1—S1	−6.76 (18)	C4—C5—C6—C7	−0.1 (5)
N2i—Zn1—O1—S1	−56.9 (4)	C5—C6—C7—C11	1.0 (5)
N2—Zn1—O1—S1	139.5 (3)	C5—C6—C7—C8	−177.5 (3)
N1—Zn1—O1—S1	56.1 (3)	C11—C7—C8—C9	−0.3 (5)
N1i—Zn1—O1—S1	−128.2 (3)	C6—C7—C8—C9	178.2 (3)
S1i—S1—O2—O1i	−30 (2)	C7—C8—C9—C10	1.2 (5)
O4i—S1—O2—O1i	129.5 (6)	C11—N2—C10—C9	−0.2 (5)
O3—S1—O2—O1i	135.8 (6)	Zn1—N2—C10—C9	175.6 (2)
O4—S1—O2—O1i	−102.0 (4)	C8—C9—C10—N2	−1.0 (5)
O1—S1—O2—O1i	16.4 (4)	C10—N2—C11—C7	1.2 (4)
O3i—S1—O2—O1i	−110.1 (4)	Zn1—N2—C11—C7	−175.3 (2)
O2i—S1—O2—O1i	3.7 (5)	C10—N2—C11—C12	−177.5 (3)
O1i—S1—O2—S1i	30 (2)	Zn1—N2—C11—C12	6.1 (3)
O4i—S1—O2—S1i	159 (2)	C8—C7—C11—N2	−0.9 (5)
O3—S1—O2—S1i	165 (2)	C6—C7—C11—N2	−179.5 (3)
O4—S1—O2—S1i	−72 (2)	C8—C7—C11—C12	177.7 (3)
O1—S1—O2—S1i	46 (2)	C6—C7—C11—C12	−0.9 (4)
O3i—S1—O2—S1i	−81 (2)	C1—N1—C12—C4	−0.8 (4)
O2i—S1—O2—S1i	33.3 (16)	Zn1—N1—C12—C4	174.9 (2)
S1i—S1—O3—O4i	128 (7)	C1—N1—C12—C11	176.2 (3)
O1i—S1—O3—O4i	25 (8)	Zn1—N1—C12—C11	−8.1 (3)
O2—S1—O3—O4i	−47 (7)	C3—C4—C12—N1	−0.2 (5)
O4—S1—O3—O4i	−169 (7)	C5—C4—C12—N1	178.0 (3)
O1—S1—O3—O4i	73 (7)	C3—C4—C12—C11	−177.1 (3)
O3i—S1—O3—O4i	−162 (7)	C5—C4—C12—C11	1.1 (4)
O2i—S1—O3—O4i	114 (7)	N2—C11—C12—N1	1.5 (4)
O1i—S1—O3—S1i	−103.3 (8)	C7—C11—C12—N1	−177.3 (3)
O4i—S1—O3—S1i	−128 (7)	N2—C11—C12—C4	178.6 (3)
O2—S1—O3—S1i	−175.2 (6)	C7—C11—C12—C4	−0.1 (4)
O4—S1—O3—S1i	62.4 (7)	O5—C13—C14—O6	67.9 (12)
O1—S1—O3—S1i	−55.1 (4)	O5—C13—C14—C15	−166.6 (14)
O3i—S1—O3—S1i	69.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3	0.83	2.00	2.74 (3)	149
O6—H6···O4	0.83	2.11	2.89 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O3	0.83	2.00	2.74 (3)	149
O6—H6⋯O4	0.83	2.11	2.89 (2)	155