Three overcrowded zinc(II) complexes with potentially hexa­dentate poly­pyridyl ligands

In each of [N,N,N′,N′-tetra­kis(2-pyridyl­methyl)­ethane-1,2-diamine-κ⁶N]zinc(II) bis(perchlorate) 0.67-hydrate, [Zn(C₂₆H₂₈N₆)](ClO₄)₂·0.67H₂O, (I), [N,N,N′-tris­(2-pyridylmethyl)-N′-(2-quinolyl­methyl)­ethane-1,2-diamine-κ⁶N]zinc(II) bis(perchlorate), [Zn(C₃₀H₃₀N₆)](ClO₄)₂, (II), and [N,N′-bis­(2-pyri­dyl­methyl)-N,N′-bis­(2-quinolyl­methyl)­ethane-1,2-diamine-κ⁶N]zinc(II) bis(perchlorate) monohydrate, [Zn(C₃₄H₃₂N₆)](ClO₄)₂·H₂O, (III), the Zn atom is coordinated to all six N atoms of the ligand. Compound (I) has one complex cation in a general position and one on a twofold axis. The coordination environments are inter­mediate between a regular octa­hedron and a penta­gonal bipyramid which lacks one equatorial bond; complexes (II) and (III) are shown to be closer to the latter description. The quinolyl groups are in equatorial positions and the deviation from octa­hedral geometry increases with the number of these groups. This study demonstrates the systematic changes in the geometry at the central Zn atom as the overlap between the ligands increases.

S1. Comment

Ligands based on N,N,N',N'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine (tpen) are potentially hexadentate, but some metal atoms such as chromium(III) also form complexes in which only five or four N atoms are coordinated (Eriksen et al., 1999). Recently, this type of hexadentate ligand, with all four of the pyridyl groups replaced by quinonyl groups, has attracted interest as a fluorescent sensor for zinc(II) (Mikata et al., 2005). This work reports the structures of three zinc(II) complexes with the tpen ligand and with ligands in which an intermediate number of pyridyl groups have been replaced by quinonyl groups (see scheme). The three zinc(II) complexes with the tpen ligand, (I), the qtpen ligand, (II) [qtpen is N-mono(2-quinolmethyl)-N,N',N'-tris(2-pyridylmethyl)ethane-1,2-diamine], and the bqpben ligand, (III) [bqpben is N,N'-bis(2-quinolmethyl)-N,N',-bis(2-pyridylmethyl)ethane-1,2-diamine], have all been isolated as perchlorate salts. In each of the three cations, all six N atoms are coordinated to Zn^II.

Compound (I), [Zn(tpen)](ClO₄)₂·0.67H₂O (Fig 1), crystallizes with one complex cation in a general position and with one on a twofold rotation axis. The perchlorate ions and the water molecule are all in general positions. The structure is very similar to that of [Zn(tpen)](ClO₄)₂·0.67CH₃OH, (IV) (Mikata et al., 2005), which differs from (I) only in the solvate molecule being methanol. For compounds (II), [Zn(qtpen)](ClO₄)₂ (Fig 2), and (III), [Zn(bqbpen)](ClO₄)₂·H₂O (Fig 3), the coordination around Zn^II is very similar to that in [Zn(tpen)]²⁺, with the quinonyl groups in the equatorial positions. Both sp³ N atoms have the S configuration for the crystal studied. There is an intramolecular C—H..π bond involving atom H3 of an axial pyridine group and the phenyl ring of the equatorial quinonyl group in (II).

The coordination polyhedron around the Zn^II centres is irregular (Tables 4 and 5) and is closer to being a pentagonal bipyramid, with N3—Zn1—N6 as the axis and with one equatorial bond lacking, than it is to being a regular octahedron. The two possibilities were compared by constructing an observed polyhedron with unit bond lengths and calculating the r.m.s. values, δ_oct, of the deviations of the positions, δ, from those of an ideal octahedron with bond angles all 90° and those, δ_pbp, of an ideal pentagonal bipyramid with eight bond angles of 90°, three of 72° and one of 144°. These calculations gave δ_oct = 0.191 (38) and 0.185 (18) Å and δ_pbp = 0.172 (7) and 0.151 (8) Å for the two [Zn(tpen)]²⁺ cations in (I), δ_oct = 0.198 (24) Å and δ_pbp = 0.133 (4) Å for the [Zn(qtpen)]²⁺ cation in (II), and δ_oct = 0.217 (32) Å and δ_pbp = 0.102 (3) Å for the [Zn(bqbpen)]²⁺ cation in (III).

Another aspect of the introduction of quinonyl groups in the equatorial plane is an increase of the N4—Zn—N5 angle from 119.5 (1) and 121.0 (1)° in [Zn(tpen)]²⁺, to 125.04 (1)° in [Zn(qtpen)]²⁺ and 129.8 (1)° in [Zn(bqbpen)]²⁺. This distortion is accompanied by a twisting of the equatorial aromatic groups out of the plane defined by the Zn^II atom and the four equatorial N atoms. The twist angle is in the range 8.2 (2)–10.7 (3)° for the pyridine rings in the two [Zn(tpen)]²⁺ cations and is 14.6 (2)° in (II). The quinoline ring systems are twisted even more, by 22.0 (2)° in (II), and by 23.5 (2) and 25.8 (2)° in (III). The Zn—N bond lengths vary between 2.082 (3) and 2.236 (3) Å in the four complex cations. The variation of the Zn—N bond lengths from Zn^II to the N atoms of the ethane-1,2-diamine part of the ligands behaves normally, but the bond lengths to the aromatic ligands are much more irregular, particularly when the ligand with four quinonyl groups, (IV) (Mikata et al., 2005) is included in the comparisons. This last complex, (IV), also exhibits overcrowding of the axial quinonyl groups, resulting in very long bonds to the axial N atoms of the ligands of 2.401 (2) and 2.371 (2) Å, compared with an average of 2.138 (1) Å here for (II) and (III). Generally, the bond lengths to the axial N atoms decrease as the number of equatorial quinonyl groups increases. This general observation is more specific when the correlation between the lengths d_eq and d_ax is considered (Fig. 4): for a given cation in a general position, the longest axial bond is paired with that of the closest equatorial aromatic system. This almost linear correlation, shown in Fig. 4 (gradient −0.823, regression coefficient −0.964 for eight points), may be explained by the interaction between an H atom of the axial pyridyl group and the π-system of the closest equatorial aromatic system. For the cations in special positions, there are two aromatic systems which are equally close and the points for these lie below the regression line.

In compound (I), the Zn and Cl atoms and the water molecules pack in layers perpendicular to the b axis at y = ±1/4. Within the layers, the cations form zigzag chains parallel to the (101) direction (Fig. 5). The two independent cations are linked by C—H···π hydrogen bonds and the cation which is in a general position is hydrogen-bonded to a symmetry-related cation. These hydrogen bonds link the cations into infinite chains, and these chains are separated by perchlorate ions and water molecules. In the layer at y = ±3/4, the chains are displaced by c/2 so that they are above the perchlorate ions of the neighbouring layer. The packing interactions are hydrogen bonds of the O—H···O(perchlorate) and C—H···π types (Table 1).

In (II), the cations lie in layers parallel to the (101) plane; intermolecular C—H···π hydrogen bonds link pairs of cations (Fig. 6). The dimers are close-packed within these layers and are almost superimposed on those of the neighbouring layer. The perchlorate ions are located between the layers so that the packing utilizes C—H···O and C—H···π interactions (Table 2).

In (III), the cations pack alternately up the 2₁ screw axes parallel to b at (0, y, 1/4) and (1/2, y, 3/4), giving close-packed columns with the perchlorate ions and water molecules in the spaces between these columns (Fig. 7). The axial Zn—N bonds are parallel to b, resulting in open channels parallel to the b axis. C—H···π bonds link the cation columns along the 2₁ axis. The C—H···π, O—H···O(perchlorate) and C—H···O interactions are listed in Table 3.

In a large proportion of their salts, perchlorate anions tend to be disordered, which results in large apparent displacement parameters. Here, in ccompounds (I) and (II) [Should this be (III)?], which are both hydrates, the water molecules are hydrogen-bonded to two perchlorate ions, ensuring the anions are ordered. In the anhydrous compound, (III) [Should this be (II)?], one of the perchlorate ions (Cl1) was so disordered that it was modelled as two interpenetrating regular tetrahedra, but even then the U₃/U₁ value was unrealistically high.

S2. Experimental

Caution: Perchlorate salts and ethanolic solutions of perchlorate salts are potentially explosive, and should be handled accordingly.

For [Zn(tpen)](ClO₄)₂·2H₂O, a solution of zinc perchlorate hexahydrate (0.896 g, 2.4 mmol) in absolute ethanol (15 ml) was added slowly to a solution of tpen (1 g, 2.4 mmol) in absolute ethanol (10 ml). The mixture was stirred for 30 min at 333 K and then cooled to room temperature. The white crystals which formed were filtered off and washed with ethanol (5 ml) (yield 1.49 g, 92%). The crystals were recrystallized from a mixture of water and ethanol (1:1 v/v). Analysis, found: C 45.36, H 3.94, N 12.09, Cl 9.51%; calculated for {[C₂₆H₂₈N₆Zn](ClO₄)₂}₃·2H₂O: C 44.56, H 4.22, N 11.99, Cl 10.18%.

For [Zn(qtpen](ClO₄)₂, a solution of zinc perchlorate hexahydrate (0.785 g, 2.11 mmol) in absolute ethanol (12 ml) was added slowly to a solution of qtpen (1 g, 2.11 mmol) in absolute ethanol (12 ml), which was heated to 323 K. The mixture was cooled to room temperature and the white crystals which formed were filtered off and washed with ice-cold ethanol (4 ml) (yield 1.4 g, 94%). The crystals were dissolved in boiling water, filtered and cooled to room temperature (yield 1.3 g, 85%). Analysis, found: C 48.83, H 3.79, N 11.37, Cl 9.43%; calculated for [C₃₀H₃₀N₆Zn](ClO₄)₂: C 44.77, H 4.09, N 11.37, Cl 9.60%.

For [Zn(bqbpen)](ClO₄)₂·H₂O, a solution of zinc perchlorate hexahydrate (0.524 g, 1.4 mmol) in absolute ethanol (10 ml) was added slowly to a solution of bqbppen (0.74 g, 1.4 mmol) in absolute ethanol (12 ml), which was heated to 333 K. The mixture was cooled to room temperature and the white crystals which formed were filtered off and washed with ethanol (5 ml) (yield 1 g, 90%). The crystals were dissolved in boiling water, filtered and cooled to room temperature. Analysis, found: C 51.17, H 4.03, N 10.47, Cl 8.73%; calculated for [C₃₄H₃₂N₆Zn](ClO₄)₂·H₂O: C 50.60, H 4.25, N 10.41, Cl 8.79%.

S3. Refinement

Water-bound H atoms were refined isotropically [Range of O—H distances?]. [Contradicts CIF data tables - O-bound H atoms in (I), (II) and (III) are constrained] Carbon-bound H atoms were fixed in calculated positions, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). In (II), one of the perchlorate groups is disordered and was modelled as two interpenetrating regular tetrahedra with a common Cl—O distance and combined occupancy factors of unity for the two tetrahedra. For (III), a Rogers parameter (Rogers, 1981) refined to 0.93 (2), defining the cation as chiral with the Δ configuration in the crystal studied.

Computing details

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1997) and KRYSTAL (Hazell, 1995); program(s) used to refine structure: ORFLS (Busing et al., 1962; modified) and KRYSTAL (Hazell, 1995); molecular graphics: ORTEPIII (Burnett and Johnson, 1996), KRYSTAL (Hazell, 1995) and PLATON (Spek, 2003); software used to prepare material for publication: KRYSTAL (Hazell, 1995).

Figures

	Fig. 1. A view of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Most H atoms have been omitted for clarity. The perclorate Cl3 atom is drawn at (1 − x, 1 + y, 3/2 − z) to avoid overlap. Intramolecular C—H···π and O—H···O hydrogen bonds are represented by dashed lines. [Symmetry code: (i) 1 − x, y, 1/2 − z; (ii) x, 1 − y, −1/2 + z.]
	Fig. 2. A view of (II) showing the atom-labelling scheme; atoms Cl1 and Cl1' are superimposed. Displacement ellipsoids are shown at the 50% probability levels. Most H atoms have been omitted for clarity. The intramolecular C—H···π bond is represented by a dashed line.
	Fig. 3. A view of (III), showing the atom-labelling scheme. Perchlorate groups are drawn at (x − 1, y, z). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 4. The correlation between equatorial and axial Zn—N bond lengths for which the distance between an H atom of an axial pyridyl group and the closest equatorial aromatic π-system is lowest. Filled circles: this work; filled squares: compound (IV), [Zn(tpen)]^2+ (Mikata et al., 2005). Points for the cations in special positions are shown as open circles for (I) and squares for (IV).
	Fig. 5. A packing diagram for (I), showing the slice (y = 0 to 1/2) perpendicular to the b axis. Intermolecular C—H···π bonds are shown as dashed lines. H atoms have been omitted, except for those of the water molecule and those of the C—H···π bonds.
	Fig. 6. Packing diagram for (II), showing the slice (0, y, 0) to (1/2, y, 1/2) parallel to {1 0 1}. Intermolecular C—H···π bonds are shown as dashed lines. H atoms have been omitted except for those of the C—H···π bonds.
	Fig. 7. Unit-cell contents of (III), viewed down the b axis. H atoms have been omitted for clarity except for those of the water molecule.

(I) [N,N,N',N'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine-κ⁶N]zinc(II) diperchlorate 0.67-hydrate

Crystal data

[Zn(C26H28N6)](ClO4)2·0.67H2O	F(000) = 4328.0
Mr = 700.86	Dx = 1.603 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8192 reflections
a = 41.064 (3) Å	θ = 1.8–29.8°
b = 9.3590 (7) Å	µ = 1.09 mm^−1
c = 23.785 (2) Å	T = 120 K
β = 107.625 (2)°	Block, colourless
V = 8711.9 (12) Å^3	0.41 × 0.26 × 0.08 mm
Z = 12

Data collection

Siemens SMART CCD area-detector diffractometer	10019 independent reflections
Radiation source: x-ray tube	6179 reflections with I > 2.5σ(I)
Graphite monochromator	Rint = 0.063
ω rotation scans with narrow frames	θmax = 27.5°, θmin = 1.8°
Absorption correction: integration (XPREP; Siemens, 1995)	h = −54→54
Tmin = 0.681, Tmax = 0.919	k = −12→13
41218 measured reflections	l = −31→24

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.038	w = 1/{[σcs(F^2) + B + (1 + A)F^2]^1/2-|F|}^2 where A = 0.03 and B = 0.5
S = 0.99	(Δ/σ)max = 0.003
6179 reflections	Δρmax = 0.55 (4) e Å^−3
591 parameters	Δρmin = −0.35 (4) e Å^−3

Special details

Refinement. Sfls: F calc weight full matrix

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.669763 (9)	0.24994 (4)	0.59094 (2)	0.0202 (2)
Zn2	0.500000	0.29968 (6)	0.25000	0.0198 (3)
Cl1	0.67788 (2)	0.73073 (8)	0.71405 (4)	0.0229 (5)
Cl2	0.65166 (2)	0.72043 (10)	0.37534 (4)	0.0340 (6)
Cl3	0.50834 (2)	0.18391 (9)	0.60638 (4)	0.0237 (5)
O1	0.67150 (7)	0.5941 (3)	0.7357 (1)	0.041 (2)
O2	0.68619 (6)	0.8302 (3)	0.7628 (1)	0.038 (2)
O3	0.70622 (7)	0.7204 (3)	0.6908 (1)	0.042 (2)
O4	0.64802 (7)	0.7790 (3)	0.6701 (1)	0.043 (2)
O5	0.64101 (10)	0.8245 (4)	0.4101 (2)	0.083 (3)
O6	0.67075 (10)	0.6158 (4)	0.4146 (1)	0.079 (3)
O7	0.67339 (9)	0.7924 (4)	0.3491 (2)	0.083 (3)
O8	0.62397 (9)	0.6672 (4)	0.3322 (2)	0.099 (3)
O9	0.52684 (10)	0.0782 (3)	0.5876 (2)	0.090 (4)
O10	0.47742 (8)	0.2089 (4)	0.5588 (1)	0.066 (2)
O11	0.49856 (7)	0.1390 (3)	0.6557 (1)	0.047 (2)
O12	0.52683 (6)	0.3153 (3)	0.6170 (1)	0.037 (2)
O13	0.67950 (9)	0.3237 (3)	0.3802 (1)	0.070 (3)
N1	0.70714 (6)	0.2480 (3)	0.6789 (1)	0.022 (2)
N2	0.63440 (7)	0.2006 (3)	0.6401 (1)	0.022 (2)
N3	0.69408 (7)	0.0359 (3)	0.5919 (1)	0.023 (2)
N4	0.71103 (7)	0.3500 (3)	0.5728 (1)	0.021 (2)
N5	0.62857 (7)	0.1795 (3)	0.5215 (1)	0.024 (2)
N6	0.64201 (7)	0.4533 (3)	0.5839 (1)	0.022 (2)
N7	0.53684 (7)	0.4778 (3)	0.2745 (1)	0.026 (2)
N8	0.54605 (7)	0.1897 (3)	0.2613 (1)	0.022 (2)
N9	0.50799 (7)	0.3136 (3)	0.3445 (1)	0.022 (2)
C1	0.68679 (8)	0.2502 (4)	0.7206 (1)	0.026 (2)
C2	0.65616 (9)	0.1520 (4)	0.6990 (2)	0.025 (2)
C3	0.68734 (9)	−0.0610 (4)	0.5482 (2)	0.028 (2)
C4	0.70974 (10)	−0.1679 (4)	0.5452 (2)	0.034 (3)
C5	0.74100 (10)	−0.1735 (4)	0.5879 (2)	0.036 (3)
C6	0.74845 (9)	−0.0753 (4)	0.6334 (2)	0.029 (2)
C7	0.72385 (9)	0.0251 (3)	0.6352 (2)	0.024 (2)
C8	0.72962 (9)	0.1215 (4)	0.6873 (2)	0.034 (2)
C9	0.71683 (9)	0.3664 (4)	0.5206 (2)	0.025 (2)
C10	0.74628 (9)	0.4261 (4)	0.5151 (2)	0.028 (2)
C11	0.77120 (9)	0.4707 (4)	0.5657 (2)	0.028 (2)
C12	0.76535 (8)	0.4556 (4)	0.6193 (2)	0.025 (2)
C13	0.73520 (8)	0.3954 (3)	0.6218 (2)	0.022 (2)
C14	0.72656 (8)	0.3807 (3)	0.6789 (2)	0.023 (2)
C15	0.62333 (9)	0.1965 (4)	0.4633 (2)	0.029 (2)
C16	0.59540 (9)	0.1404 (4)	0.4216 (2)	0.029 (2)
C17	0.57175 (9)	0.0648 (4)	0.4400 (2)	0.030 (2)
C18	0.57622 (9)	0.0506 (3)	0.4995 (2)	0.026 (2)
C19	0.60513 (8)	0.1087 (3)	0.5396 (2)	0.021 (2)
C20	0.61315 (9)	0.0846 (4)	0.6056 (2)	0.028 (2)
C21	0.64351 (8)	0.5609 (4)	0.5472 (2)	0.026 (2)
C22	0.61850 (9)	0.6630 (4)	0.5286 (2)	0.027 (2)
C23	0.59037 (9)	0.6551 (4)	0.5490 (2)	0.027 (2)
C24	0.58833 (8)	0.5447 (4)	0.5867 (2)	0.025 (2)
C25	0.61449 (8)	0.4460 (3)	0.6031 (1)	0.021 (2)
C26	0.61381 (9)	0.3276 (4)	0.6455 (2)	0.028 (2)
C27	0.51785 (10)	0.6051 (4)	0.2461 (2)	0.034 (2)
C28	0.55232 (9)	0.0490 (4)	0.2699 (2)	0.025 (2)
C29	0.58431 (9)	−0.0096 (4)	0.2788 (2)	0.033 (2)
C30	0.61089 (10)	0.0805 (4)	0.2795 (2)	0.040 (3)
C31	0.60482 (9)	0.2250 (4)	0.2706 (2)	0.036 (3)
C32	0.57228 (9)	0.2768 (4)	0.2613 (1)	0.025 (2)
C33	0.56386 (9)	0.4335 (4)	0.2490 (2)	0.031 (2)
C34	0.49215 (8)	0.2348 (4)	0.3758 (2)	0.026 (2)
C35	0.49819 (9)	0.2522 (4)	0.4356 (2)	0.030 (2)
C36	0.52075 (10)	0.3562 (4)	0.4645 (2)	0.033 (2)
C37	0.53750 (10)	0.4362 (4)	0.4331 (2)	0.031 (2)
C38	0.53074 (9)	0.4111 (3)	0.3733 (2)	0.024 (2)
C39	0.55044 (10)	0.4926 (4)	0.3396 (2)	0.031 (2)
H131	0.67449	0.4113	0.3848	0.100*
H132	0.68475	0.2974	0.3494	0.100*
H1a	0.67911	0.3449	0.7235	0.031*
H1b	0.70061	0.2190	0.7583	0.031*
H2a	0.66377	0.0572	0.6961	0.031*
H2b	0.64326	0.1542	0.7261	0.031*
H3	0.66609	−0.0554	0.5179	0.034*
H4	0.70375	−0.2365	0.5143	0.041*
H5	0.75729	−0.2440	0.5861	0.043*
H6	0.77001	−0.0765	0.6630	0.035*
H8a	0.72641	0.0670	0.7188	0.041*
H8b	0.75257	0.1544	0.6976	0.041*
H9	0.69983	0.3353	0.4859	0.030*
H10	0.74950	0.4366	0.4774	0.033*
H11	0.79198	0.5111	0.5633	0.034*
H12	0.78200	0.4865	0.6544	0.030*
H14a	0.74711	0.3782	0.7109	0.028*
H14b	0.71318	0.4602	0.6833	0.028*
H15	0.63956	0.2492	0.4505	0.035*
H16	0.59244	0.1536	0.3808	0.035*
H17	0.55255	0.0228	0.4120	0.035*
H18	0.55972	0.0016	0.5129	0.031*
H20a	0.59231	0.0801	0.6151	0.033*
H20b	0.62505	−0.0033	0.6157	0.033*
H21	0.66290	0.5666	0.5334	0.031*
H22	0.62045	0.7369	0.5024	0.033*
H23	0.57270	0.7244	0.5374	0.033*
H24	0.56920	0.5372	0.6011	0.030*
H26a	0.62244	0.3638	0.6845	0.034*
H26b	0.59077	0.2982	0.6384	0.034*
H27a	0.51435	0.6080	0.2048	0.041*
H27b	0.52802	0.6920	0.2635	0.041*
H28	0.53392	−0.0126	0.2699	0.030*
H29	0.58789	−0.1096	0.2844	0.039*
H30	0.63327	0.0435	0.2860	0.048*
H31	0.62298	0.2882	0.2710	0.043*
H33a	0.58381	0.4889	0.2660	0.037*
H33b	0.55617	0.4486	0.2075	0.037*
H34	0.47618	0.1643	0.3558	0.031*
H35	0.48696	0.1934	0.4565	0.036*
H36	0.52471	0.3726	0.5055	0.040*
H37	0.55346	0.5076	0.4523	0.037*
H39a	0.55007	0.5910	0.3492	0.037*
H39b	0.57336	0.4591	0.3518	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0177 (2)	0.0188 (2)	0.0225 (2)	−0.0002 (2)	0.0036 (2)	−0.0001 (2)
Zn2	0.0251 (3)	0.0150 (3)	0.0184 (3)	0.0000	0.0052 (2)	0.0000
Cl1	0.0232 (4)	0.0160 (4)	0.0287 (5)	0.0033 (3)	0.0066 (4)	0.0012 (4)
Cl2	0.0298 (5)	0.0363 (6)	0.0357 (6)	0.0027 (4)	0.0095 (4)	0.0016 (4)
Cl3	0.0272 (5)	0.0200 (4)	0.0271 (5)	−0.0035 (4)	0.0128 (4)	−0.0017 (4)
O1	0.057 (2)	0.020 (1)	0.059 (2)	0.002 (1)	0.034 (2)	0.008 (1)
O2	0.036 (2)	0.034 (2)	0.036 (2)	0.002 (1)	0.000 (1)	−0.014 (1)
O3	0.043 (2)	0.037 (2)	0.057 (2)	0.006 (1)	0.031 (1)	0.010 (1)
O4	0.042 (2)	0.037 (2)	0.037 (2)	0.010 (1)	−0.006 (1)	−0.004 (1)
O5	0.115 (3)	0.075 (3)	0.074 (3)	0.037 (2)	0.054 (2)	−0.003 (2)
O6	0.111 (3)	0.060 (2)	0.057 (2)	0.035 (2)	0.012 (2)	0.015 (2)
O7	0.071 (2)	0.113 (3)	0.071 (3)	−0.034 (2)	0.033 (2)	0.006 (2)
O8	0.066 (2)	0.064 (2)	0.129 (4)	−0.025 (2)	−0.027 (2)	−0.017 (2)
O9	0.125 (3)	0.037 (2)	0.153 (4)	0.000 (2)	0.109 (3)	−0.015 (2)
O10	0.057 (2)	0.077 (2)	0.048 (2)	−0.027 (2)	−0.011 (2)	0.017 (2)
O11	0.072 (2)	0.044 (2)	0.032 (2)	−0.028 (2)	0.028 (2)	−0.006 (1)
O12	0.042 (2)	0.030 (1)	0.042 (2)	−0.016 (1)	0.018 (1)	−0.003 (1)
O13	0.108 (3)	0.052 (2)	0.041 (2)	0.012 (2)	0.011 (2)	−0.007 (2)
N1	0.023 (1)	0.016 (1)	0.026 (2)	0.002 (1)	0.003 (1)	0.000 (1)
N2	0.022 (1)	0.020 (1)	0.023 (2)	0.002 (1)	0.004 (1)	0.006 (1)
N3	0.022 (2)	0.017 (1)	0.028 (2)	−0.003 (1)	0.008 (1)	−0.004 (1)
N4	0.019 (1)	0.018 (1)	0.025 (2)	0.002 (1)	0.004 (1)	−0.002 (1)
N5	0.021 (1)	0.025 (2)	0.025 (2)	−0.002 (1)	0.005 (1)	0.001 (1)
N6	0.019 (1)	0.019 (1)	0.026 (2)	−0.001 (1)	0.006 (1)	0.002 (1)
N7	0.038 (2)	0.019 (2)	0.019 (2)	−0.005 (1)	0.007 (1)	−0.001 (1)
N8	0.024 (2)	0.022 (1)	0.017 (2)	−0.002 (1)	0.005 (1)	0.000 (1)
N9	0.028 (2)	0.020 (1)	0.018 (2)	0.000 (1)	0.006 (1)	0.001 (1)
C1	0.028 (2)	0.023 (2)	0.023 (2)	0.000 (2)	0.003 (1)	0.004 (2)
C2	0.029 (2)	0.022 (2)	0.023 (2)	−0.001 (2)	0.005 (2)	0.007 (2)
C3	0.030 (2)	0.023 (2)	0.036 (2)	−0.010 (2)	0.017 (2)	−0.006 (2)
C4	0.051 (3)	0.015 (2)	0.047 (3)	−0.009 (2)	0.031 (2)	−0.006 (2)
C5	0.046 (2)	0.016 (2)	0.058 (3)	0.007 (2)	0.034 (2)	0.007 (2)
C6	0.027 (2)	0.021 (2)	0.043 (3)	0.004 (2)	0.016 (2)	0.012 (2)
C7	0.024 (2)	0.015 (2)	0.033 (2)	−0.001 (1)	0.011 (2)	0.004 (2)
C8	0.034 (2)	0.024 (2)	0.038 (3)	0.010 (2)	−0.001 (2)	0.000 (2)
C9	0.029 (2)	0.023 (2)	0.024 (2)	0.000 (2)	0.007 (2)	−0.002 (2)
C10	0.032 (2)	0.024 (2)	0.032 (2)	0.001 (2)	0.015 (2)	−0.001 (2)
C11	0.022 (2)	0.024 (2)	0.041 (3)	0.000 (2)	0.011 (2)	0.003 (2)
C12	0.020 (2)	0.021 (2)	0.031 (2)	0.001 (1)	0.005 (2)	−0.001 (2)
C13	0.021 (2)	0.015 (2)	0.028 (2)	0.005 (1)	0.005 (2)	−0.001 (1)
C14	0.020 (2)	0.020 (2)	0.028 (2)	−0.001 (1)	0.004 (2)	−0.006 (2)
C15	0.028 (2)	0.030 (2)	0.029 (2)	−0.002 (2)	0.009 (2)	0.000 (2)
C16	0.025 (2)	0.035 (2)	0.023 (2)	0.001 (2)	0.002 (2)	−0.004 (2)
C17	0.023 (2)	0.026 (2)	0.032 (2)	−0.004 (2)	−0.001 (2)	−0.006 (2)
C18	0.025 (2)	0.019 (2)	0.032 (2)	−0.004 (1)	0.007 (2)	0.002 (2)
C19	0.020 (2)	0.017 (2)	0.025 (2)	0.002 (1)	0.003 (2)	0.001 (1)
C20	0.026 (2)	0.023 (2)	0.031 (2)	−0.006 (2)	0.005 (2)	0.004 (2)
C21	0.023 (2)	0.023 (2)	0.033 (2)	−0.003 (2)	0.008 (2)	0.002 (2)
C22	0.030 (2)	0.019 (2)	0.029 (2)	−0.003 (2)	0.002 (2)	0.006 (2)
C23	0.024 (2)	0.019 (2)	0.033 (2)	0.004 (1)	−0.001 (2)	−0.001 (2)
C24	0.022 (2)	0.024 (2)	0.030 (2)	−0.001 (1)	0.007 (2)	−0.003 (2)
C25	0.021 (2)	0.018 (2)	0.022 (2)	−0.002 (1)	0.004 (2)	−0.003 (1)
C26	0.028 (2)	0.026 (2)	0.034 (2)	0.004 (2)	0.015 (2)	0.006 (2)
C27	0.057 (3)	0.013 (2)	0.029 (2)	−0.007 (2)	0.009 (2)	0.002 (2)
C28	0.027 (2)	0.022 (2)	0.025 (2)	−0.004 (2)	0.006 (2)	−0.004 (2)
C29	0.032 (2)	0.030 (2)	0.037 (2)	0.005 (2)	0.012 (2)	−0.007 (2)
C30	0.029 (2)	0.048 (3)	0.046 (3)	0.002 (2)	0.017 (2)	−0.015 (2)
C31	0.030 (2)	0.041 (3)	0.041 (2)	−0.009 (2)	0.017 (2)	−0.012 (2)
C32	0.032 (2)	0.026 (2)	0.019 (2)	−0.007 (2)	0.011 (2)	−0.005 (1)
C33	0.035 (2)	0.032 (2)	0.026 (2)	−0.013 (2)	0.010 (2)	−0.001 (2)
C34	0.028 (2)	0.024 (2)	0.026 (2)	0.002 (2)	0.008 (2)	0.001 (2)
C35	0.035 (2)	0.033 (2)	0.027 (2)	0.005 (2)	0.015 (2)	0.005 (2)
C36	0.048 (2)	0.031 (2)	0.020 (2)	0.005 (2)	0.010 (2)	−0.004 (2)
C37	0.041 (2)	0.025 (2)	0.023 (2)	−0.002 (2)	0.004 (2)	−0.004 (2)
C38	0.032 (2)	0.019 (2)	0.019 (2)	0.004 (2)	0.004 (2)	0.000 (1)
C39	0.042 (2)	0.023 (2)	0.026 (2)	−0.010 (2)	0.009 (2)	−0.007 (2)

Geometric parameters (Å, º)

Zn1—N1	2.188 (3)	C21—C22	1.374 (5)
Zn1—N2	2.173 (3)	C22—C23	1.384 (5)
Zn1—N3	2.236 (3)	C23—C24	1.387 (5)
Zn1—N4	2.092 (3)	C24—C25	1.380 (4)
Zn1—N5	2.082 (3)	C25—C26	1.504 (5)
Zn1—N6	2.199 (3)	C27—C27^i	1.532 (8)
Zn2—N7	2.208 (3)	C28—C29	1.380 (5)
Zn2—N7^i	2.208 (3)	C29—C30	1.376 (5)
Zn2—N8	2.097 (3)	C30—C31	1.380 (5)
Zn2—N8^i	2.097 (3)	C31—C32	1.375 (5)
Zn2—N9	2.175 (3)	C32—C33	1.515 (5)
Zn2—N9^i	2.175 (3)	C34—C35	1.377 (5)
Cl1—O1	1.432 (2)	C35—C36	1.376 (5)
Cl1—O2	1.446 (2)	C36—C37	1.380 (5)
Cl1—O3	1.435 (2)	C37—C38	1.384 (5)
Cl1—O4	1.423 (2)	C38—C39	1.507 (5)
Cl2—O5	1.430 (3)	O13—H131	0.860
Cl2—O6	1.415 (3)	O13—H132	0.860
Cl2—O7	1.406 (3)	C1—H1a	0.950
Cl2—O8	1.374 (3)	C1—H1b	0.950
Cl3—O9	1.401 (3)	C2—H2b	0.950
Cl3—O10	1.441 (3)	C2—H2a	0.950
Cl3—O11	1.414 (3)	C3—H3	0.950
Cl3—O12	1.428 (2)	C4—H4	0.950
N1—C14	1.476 (4)	C5—H5	0.950
N1—C8	1.477 (4)	C6—H6	0.950
N1—C1	1.478 (4)	C8—H8a	0.950
N2—C20	1.476 (4)	C8—H8b	0.950
N2—C2	1.486 (4)	C9—H9	0.950
N2—C26	1.487 (4)	C10—H10	0.950
N3—C7	1.343 (4)	C11—H11	0.950
N3—C3	1.343 (4)	C12—H12	0.950
N4—C9	1.342 (4)	C14—H14a	0.950
N4—C13	1.351 (4)	C14—H14b	0.950
N5—C19	1.342 (4)	C15—H15	0.950
N5—C15	1.345 (4)	C16—H16	0.950
N6—C25	1.342 (4)	C17—H17	0.950
N6—C21	1.347 (4)	C18—H18	0.950
N7—C27	1.471 (4)	C20—H20a	0.950
N7—C33	1.477 (5)	C20—H20b	0.950
N7—C39	1.485 (4)	C21—H21	0.950
N8—C28	1.345 (4)	C22—H22	0.950
N8—C32	1.350 (4)	C23—H23	0.950
N9—C38	1.337 (4)	C24—H24	0.950
N9—C34	1.346 (4)	C26—H26a	0.950
C1—C2	1.516 (4)	C26—H26b	0.950
C3—C4	1.376 (5)	C27—H27a	0.950
C4—C5	1.375 (5)	C27—H27b	0.950
C5—C6	1.382 (5)	C28—H28	0.950
C6—C7	1.390 (4)	C29—H29	0.950
C7—C8	1.492 (5)	C30—H30	0.950
C9—C10	1.375 (5)	C31—H31	0.950
C10—C11	1.387 (5)	C33—H33b	0.950
C11—C12	1.375 (5)	C33—H33a	0.950
C12—C13	1.378 (4)	C34—H34	0.950
C13—C14	1.510 (5)	C35—H35	0.950
C15—C16	1.373 (5)	C36—H36	0.950
C16—C17	1.376 (5)	C37—H37	0.950
C17—C18	1.375 (5)	C39—H39a	0.950
C18—C19	1.389 (4)	C39—H39b	0.950
C19—C20	1.521 (5)
N1—Zn1—N2	82.7 (1)	N6—C25—C26	117.0 (3)
N1—Zn1—N3	78.5 (1)	C24—C25—C26	120.7 (3)
N1—Zn1—N4	79.8 (1)	N2—C26—C25	113.9 (3)
N1—Zn1—N5	157.3 (1)	N7—C27—C27^i	109.8 (3)
N1—Zn1—N6	106.1 (1)	N8—C28—C29	122.9 (3)
N2—Zn1—N3	100.0 (1)	C28—C29—C30	118.2 (3)
N2—Zn1—N4	157.1 (1)	C29—C30—C31	119.6 (3)
N2—Zn1—N5	81.1 (1)	C30—C31—C32	119.4 (3)
N2—Zn1—N6	79.0 (1)	N8—C32—C31	121.6 (3)
N3—Zn1—N4	90.9 (1)	N8—C32—C33	116.7 (3)
N3—Zn1—N5	88.7 (1)	C31—C32—C33	121.7 (3)
N3—Zn1—N6	175.0 (1)	N7—C33—C32	110.4 (3)
N4—Zn1—N5	119.5 (1)	N9—C34—C35	122.6 (3)
N4—Zn1—N6	91.7 (1)	C34—C35—C36	119.0 (3)
N5—Zn1—N6	86.3 (1)	C35—C36—C37	118.9 (3)
N7—Zn2—N7^i	81.9 (1)	C36—C37—C38	119.1 (3)
N7—Zn2—N8	79.5 (1)	N9—C38—C37	122.3 (3)
N7^i—Zn2—N8^i	79.5 (1)	N9—C38—C39	118.5 (3)
N7—Zn2—N8^i	157.5 (1)	C37—C38—C39	119.2 (3)
N7^i—Zn2—N8	157.5 (1)	N7—C39—C38	114.5 (3)
N7—Zn2—N9	78.7 (1)	H131—O13—H132	120.7
N7^i—Zn2—N9^i	78.7 (1)	H1a—C1—H1b	109.5
N7^i—Zn2—N9	96.0 (1)	N1—C1—H1a	109.3
N7—Zn2—N9^i	96.0 (1)	C2—C1—H1a	109.3
N8—Zn2—N8^i	121.2 (1)	N1—C1—H1b	109.3
N8—Zn2—N9	92.8 (1)	C2—C1—H1b	109.3
N8^i—Zn2—N9^i	92.8 (1)	H2a—C2—H2b	109.5
N8—Zn2—N9^i	90.6 (1)	N2—C2—H2b	109.5
N8^i—Zn2—N9	90.6 (1)	C1—C2—H2b	109.5
N9—Zn2—N9^i	173.1 (1)	N2—C2—H2a	109.5
Zn1—N1—C1	105.4 (2)	C1—C2—H2a	109.5
Zn1—N1—C8	111.4 (2)	N3—C3—H3	118.4
Zn1—N1—C14	102.5 (2)	C4—C3—H3	118.4
Zn1—N2—C20	103.6 (2)	C5—C4—H4	120.7
Zn1—N2—C2	105.3 (2)	C3—C4—H4	120.7
Zn1—N3—C7	112.0 (2)	C4—C5—H5	120.4
Zn1—N2—C26	111.5 (2)	C6—C5—H5	120.3
Zn1—N3—C3	127.6 (2)	C5—C6—H6	120.6
Zn1—N4—C9	128.6 (2)	C7—C6—H6	120.5
Zn1—N4—C13	113.1 (2)	H8a—C8—H8b	109.5
Zn1—N5—C15	128.2 (2)	N1—C8—H8a	107.8
Zn1—N5—C19	113.0 (2)	C7—C8—H8a	107.9
Zn1—N6—C25	113.6 (2)	N1—C8—H8b	107.8
Zn1—N6—C21	124.9 (2)	C7—C8—H8b	107.8
Zn2—N7—C27	105.3 (2)	N4—C9—H9	118.6
Zn2—N7—C33	102.7 (2)	C10—C9—H9	118.6
Zn2—N7—C39	110.9 (2)	C9—C10—H10	120.7
Zn2—N8—C28	128.6 (2)	C11—C10—H10	120.7
Zn2—N8—C32	113.1 (2)	C12—C11—H11	120.5
Zn2—N9—C34	126.2 (2)	C10—C11—H11	120.5
Zn2—N9—C38	115.7 (2)	C11—C12—H12	120.2
O1—Cl1—O2	108.1 (2)	C13—C12—H12	120.2
O1—Cl1—O3	109.7 (2)	H14a—C14—H14b	109.5
O1—Cl1—O4	109.7 (2)	N1—C14—H14a	109.2
O2—Cl1—O3	109.3 (2)	C13—C14—H14a	109.2
O2—Cl1—O4	109.1 (1)	N1—C14—H14b	109.2
O3—Cl1—O4	110.9 (2)	C13—C14—H14b	109.2
O5—Cl2—O6	107.2 (2)	N5—C15—H15	118.8
O5—Cl2—O7	106.1 (2)	C16—C15—H15	118.8
O5—Cl2—O8	110.5 (2)	C15—C16—H16	120.6
O6—Cl2—O7	109.0 (2)	C17—C16—H16	120.6
O6—Cl2—O8	114.2 (2)	C18—C17—H17	120.3
O7—Cl2—O8	109.6 (3)	C16—C17—H17	120.4
O9—Cl3—O10	107.4 (2)	C17—C18—H18	120.4
O9—Cl3—O11	111.9 (2)	C19—C18—H18	120.4
O9—Cl3—O12	110.7 (2)	H20a—C20—H20b	109.5
O10—Cl3—O11	107.2 (2)	N2—C20—H20a	108.9
O10—Cl3—O12	107.1 (2)	C19—C20—H20a	108.9
O11—Cl3—O12	112.3 (2)	N2—C20—H20b	108.9
C8—N1—C14	111.0 (3)	C19—C20—H20b	108.9
C1—N1—C14	113.8 (3)	N6—C21—H21	118.2
C1—N1—C8	112.2 (3)	C22—C21—H21	118.2
C2—N2—C20	112.6 (3)	C21—C22—H22	120.9
C20—N2—C26	112.3 (3)	C23—C22—H22	120.9
C2—N2—C26	111.1 (3)	C22—C23—H23	120.4
C3—N3—C7	118.0 (3)	C24—C23—H23	120.4
C9—N4—C13	118.2 (3)	C25—C24—H24	120.4
C15—N5—C19	118.8 (3)	C23—C24—H24	120.5
C21—N6—C25	117.8 (3)	H26a—C26—H26b	109.5
C27—N7—C33	113.5 (3)	N2—C26—H26a	108.4
C27—N7—C39	112.5 (3)	C25—C26—H26a	108.4
C33—N7—C39	111.3 (3)	N2—C26—H26b	108.3
C28—N8—C32	118.3 (3)	C25—C26—H26b	108.3
C34—N9—C38	118.1 (3)	H27a—C27—H27b	109.4
N1—C1—C2	110.1 (3)	N7—C27—H27a	113.1
N2—C2—C1	109.5 (3)	C27^i—C27—H27a	105.9
N3—C3—C4	123.1 (3)	N7—C27—H27b	113.1
C3—C4—C5	118.6 (3)	C27^i—C27—H27b	105.0
C4—C5—C6	119.3 (3)	N8—C28—H28	118.6
C5—C6—C7	118.9 (3)	C29—C28—H28	118.6
N3—C7—C6	121.9 (3)	C30—C29—H29	120.9
N3—C7—C8	118.1 (3)	C28—C29—H29	120.9
C6—C7—C8	120.0 (3)	C29—C30—H30	120.2
N1—C8—C7	115.9 (3)	C31—C30—H30	120.2
N4—C9—C10	122.9 (3)	C32—C31—H31	120.3
C9—C10—C11	118.6 (3)	C30—C31—H31	120.3
C10—C11—C12	118.9 (3)	H33a—C33—H33b	109.5
C11—C12—C13	119.6 (3)	N7—C33—H33b	109.3
N4—C13—C12	121.8 (3)	C32—C33—H33b	109.3
N4—C13—C14	115.8 (3)	N7—C33—H33a	109.3
C12—C13—C14	122.4 (3)	C32—C33—H33a	109.2
N1—C14—C13	110.6 (3)	N9—C34—H34	118.7
N5—C15—C16	122.4 (3)	C35—C34—H34	118.7
C15—C16—C17	118.9 (4)	C36—C35—H35	120.5
C16—C17—C18	119.3 (3)	C34—C35—H35	120.5
C17—C18—C19	119.2 (3)	C35—C36—H36	120.5
N5—C19—C18	121.3 (3)	C37—C36—H36	120.6
N5—C19—C20	116.9 (3)	C36—C37—H37	120.4
C18—C19—C20	121.6 (3)	C38—C37—H37	120.4
N2—C20—C19	111.8 (3)	H39a—C39—H39b	109.5
N6—C21—C22	123.5 (3)	N7—C39—H39a	108.2
C21—C22—C23	118.1 (3)	C38—C39—H39a	108.2
C22—C23—C24	119.1 (3)	N7—C39—H39b	108.2
C23—C24—C25	119.1 (3)	C38—C39—H39b	108.2
N6—C25—C24	122.3 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O13—H131···O6	0.86	2.06	2.907 (5)	167
O13—H132···O2^ii	0.86	2.40	3.227 (4)	162
C1—H1a···O1	0.95	2.38	3.320 (5)	169
C9—H9···O13	0.95	2.40	3.250 (5)	149
C12—H12···O2^iii	0.95	2.48	3.134 (5)	126
C14—H14b···O3	0.95	2.46	3.321 (4)	150
C20—H20a···O9	0.95	2.57	3.439 (6)	153
C20—H20b···O4^iv	0.95	2.44	3.355 (5)	160
C26—H26b···O12	0.95	2.52	3.430 (5)	160
C27—H27a···O12^ii	0.95	2.41	3.287 (5)	154
C33—H33a···O8	0.95	2.53	3.440 (6)	160
C35—H35···O10	0.95	2.58	3.315 (5)	134
C10—H10···Cg3^v	0.95	2.70	3.546 (5)	148
C16—H16···Cg8	0.95	2.52	3.454 (5)	167

Symmetry codes: (ii) x, −y+1, z−1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, y−1, z; (v) −x+3/2, −y+1/2, −z+1.

(II) [N,N,N'-tris(2-pyridylmethyl)-N'-(2-quinolmethyl)ethane-1,2-diamine-κ⁶N]- diperchlorate

Crystal data

[Zn(C30H30N6)](ClO4)2	F(000) = 1520
Mr = 738.91	Dx = 1.620 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7829 reflections
a = 13.231 (2) Å	θ = 1.9–29.7°
b = 15.147 (2) Å	µ = 1.05 mm^−1
c = 15.167 (2) Å	T = 120 K
β = 94.634 (3)°	Block, colourless
V = 3029.5 (7) Å^3	0.60 × 0.42 × 0.28 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	6946 independent reflections
Radiation source: x-ray tube	4838 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.026
ω rotation scans with narrow frames	θmax = 27.5°, θmin = 1.9°
Absorption correction: integration (XPREP; Siemens, 1995	h = −17→17
Tmin = 0.596, Tmax = 0.778	k = −19→19
25310 measured reflections	l = −19→19

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	78 constraints
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.035	w = 1/{[σcs(F^2) + B (1 + A)F^2]^1/2-|F|}^2 where A = 0.03 and B = 5.7
S = 1.00	(Δ/σ)max = 0.001
4838 reflections	Δρmax = 1.43 (7) e Å^−3
402 parameters	Δρmin = −1.18 (7) e Å^−3

Special details

Refinement. Sfls: F calc weight full matrix

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.67198 (2)	0.11561 (2)	0.83858 (2)	0.0157 (1)
Cl1	0.2116 (2)	0.0433 (1)	0.5866 (1)	0.0266 (2)	0.294 (9)
O1	0.2147 (7)	−0.0109 (5)	0.6631 (4)	0.0399 (6)	0.294
O2	0.2772 (8)	0.1166 (5)	0.6029 (7)	0.0632 (10)	0.294
O3	0.1111 (4)	0.0737 (7)	0.5658 (7)	0.0563 (10)	0.294
O4	0.2436 (9)	−0.0063 (6)	0.5145 (4)	0.0615 (9)	0.294
Cl1'	0.2100 (1)	0.0434 (1)	0.5853 (1)	0.0266 (2)	0.706
O1'	0.2310 (3)	−0.0208 (2)	0.6525 (2)	0.0431 (6)	0.706
O2'	0.2278 (5)	0.1290 (1)	0.6213 (2)	0.0697 (12)	0.706
O3'	0.1071 (1)	0.0362 (4)	0.5515 (2)	0.0574 (11)	0.706
O4'	0.2741 (3)	0.0290 (3)	0.5160 (2)	0.0507 (9)	0.706
Cl2	0.39008 (5)	−0.31530 (4)	0.53154 (4)	0.0214 (3)
O5	0.4330 (2)	−0.3127 (2)	0.6212 (1)	0.046 (1)
O6	0.4700 (1)	−0.3226 (1)	0.4729 (1)	0.036 (1)
O7	0.3345 (2)	−0.2347 (1)	0.5125 (1)	0.030 (1)
O8	0.3222 (2)	−0.3887 (1)	0.5180 (2)	0.041 (1)
N1	0.7250 (2)	0.2502 (1)	0.8678 (1)	0.019 (1)
N2	0.6726 (2)	0.1639 (1)	0.6998 (1)	0.020 (1)
N3	0.5283 (2)	0.1819 (1)	0.8551 (1)	0.021 (1)
N4	0.7129 (2)	0.1115 (1)	0.9807 (1)	0.019 (1)
N5	0.5916 (2)	0.0141 (1)	0.7643 (1)	0.018 (1)
N6	0.8150 (2)	0.0660 (1)	0.8061 (1)	0.019 (1)
C1	0.7563 (2)	0.2863 (2)	0.7838 (2)	0.023 (1)
C2	0.6802 (2)	0.2614 (2)	0.7070 (2)	0.023 (1)
C3	0.4341 (2)	0.1490 (2)	0.8376 (2)	0.025 (1)
C4	0.3474 (2)	0.1974 (2)	0.8460 (2)	0.028 (1)
C5	0.3574 (2)	0.2838 (2)	0.8747 (2)	0.029 (1)
C6	0.4532 (2)	0.3189 (2)	0.8924 (2)	0.025 (1)
C7	0.5378 (2)	0.2662 (2)	0.8819 (2)	0.021 (1)
C8	0.6431 (2)	0.3023 (2)	0.9037 (2)	0.023 (1)
C9	0.6830 (2)	0.0557 (2)	1.0427 (2)	0.022 (1)
C10	0.7189 (2)	0.0604 (2)	1.1306 (2)	0.023 (1)
C11	0.7866 (2)	0.1269 (2)	1.1568 (2)	0.023 (1)
C12	0.8161 (2)	0.1857 (2)	1.0945 (2)	0.023 (1)
C13	0.7786 (2)	0.1764 (2)	1.0066 (2)	0.019 (1)
C14	0.8101 (2)	0.2387 (2)	0.9358 (2)	0.021 (1)
C15	0.5645 (2)	−0.0669 (2)	0.7956 (2)	0.019 (1)
C16	0.4904 (2)	−0.1203 (2)	0.7492 (2)	0.021 (1)
C17	0.4502 (2)	−0.0902 (2)	0.6649 (2)	0.024 (1)
C18	0.4819 (2)	−0.0120 (2)	0.6328 (2)	0.023 (1)
C19	0.5515 (2)	0.0405 (2)	0.6854 (2)	0.020 (1)
C20	0.5765 (2)	0.1326 (2)	0.6552 (2)	0.023 (1)
C21	0.8826 (2)	0.0224 (2)	0.8616 (2)	0.022 (1)
C22	0.9733 (2)	−0.0086 (2)	0.8355 (2)	0.026 (1)
C23	0.9966 (2)	0.0062 (2)	0.7492 (2)	0.028 (1)
C24	0.9274 (2)	0.0493 (2)	0.6920 (2)	0.025 (1)
C25	0.8369 (2)	0.0786 (2)	0.7221 (2)	0.020 (1)
C26	0.7599 (2)	0.1246 (2)	0.6587 (2)	0.024 (1)
C27	0.4600 (2)	−0.1999 (2)	0.7885 (2)	0.026 (1)
C28	0.5042 (2)	−0.2259 (2)	0.8691 (2)	0.027 (1)
C29	0.5825 (2)	−0.1756 (2)	0.9121 (2)	0.026 (1)
C30	0.6127 (2)	−0.0976 (2)	0.8765 (2)	0.023 (1)
H1a	0.8211	0.2632	0.7733	0.028*
H1b	0.7603	0.3488	0.7882	0.028*
H2a	0.6157	0.2852	0.7170	0.027*
H2b	0.7020	0.2848	0.6536	0.027*
H3	0.4272	0.0894	0.8184	0.030*
H4	0.2822	0.1720	0.8326	0.034*
H5	0.2991	0.3188	0.8819	0.035*
H6	0.4615	0.3784	0.9118	0.030*
H8a	0.6454	0.3605	0.8805	0.028*
H8b	0.6554	0.3043	0.9662	0.028*
H9	0.6349	0.0111	1.0252	0.026*
H10	0.6976	0.0189	1.1722	0.028*
H11	0.8124	0.1318	1.2169	0.028*
H12	0.8617	0.2323	1.1114	0.027*
H14a	0.8280	0.2943	0.9616	0.026*
H14b	0.8668	0.2148	0.9094	0.026*
H17	0.4013	−0.1248	0.6309	0.029*
H18	0.4574	0.0074	0.5755	0.028*
H20a	0.5819	0.1320	0.5931	0.027*
H20b	0.5235	0.1716	0.6685	0.027*
H21	0.8669	0.0126	0.9209	0.027*
H22	1.0191	−0.0395	0.8760	0.032*
H23	1.0595	−0.0131	0.7300	0.033*
H24	0.9412	0.0589	0.6322	0.030*
H26a	0.7937	0.1706	0.6301	0.028*
H26b	0.7345	0.0827	0.6159	0.028*
H27	0.4088	−0.2355	0.7588	0.031*
H28	0.4816	−0.2783	0.8960	0.033*
H29	0.6151	−0.1958	0.9664	0.032*
H30	0.6658	−0.0641	0.9062	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0164 (1)	0.0161 (1)	0.0146 (1)	−0.0007 (1)	0.0007 (1)	−0.0002 (1)
Cl1	0.0301 (2)	0.0212 (2)	0.0297 (2)	0.0026 (1)	0.0098 (1)	0.0053 (1)
O1	0.0290 (7)	0.0488 (6)	0.0433 (3)	0.0041 (5)	0.0108 (4)	0.0247 (4)
O2	0.0828 (12)	0.0511 (7)	0.0546 (11)	−0.0367 (10)	−0.0012 (7)	0.0095 (5)
O3	0.0346 (2)	0.0852 (16)	0.0520 (7)	0.0196 (6)	0.0201 (3)	0.0437 (9)
O4	0.0930 (13)	0.0489 (8)	0.0463 (4)	0.0185 (8)	0.0289 (6)	−0.0058 (5)
Cl1'	0.0301 (2)	0.0212 (2)	0.0297 (2)	0.0026 (1)	0.0098 (1)	0.0053 (1)
O1'	0.0353 (9)	0.0453 (4)	0.0505 (4)	0.0087 (4)	0.0147 (4)	0.0276 (4)
O2'	0.1189 (19)	0.0294 (2)	0.0626 (8)	−0.0135 (5)	0.0176 (9)	−0.0092 (3)
O3'	0.0336 (2)	0.0949 (17)	0.0437 (7)	−0.0137 (4)	0.0027 (3)	0.0389 (8)
O4'	0.0517 (7)	0.0644 (13)	0.0393 (4)	0.0241 (8)	0.0236 (5)	0.0147 (6)
Cl2	0.0239 (3)	0.0223 (3)	0.0177 (3)	0.0006 (3)	0.0005 (2)	−0.0024 (2)
O5	0.070 (2)	0.044 (1)	0.021 (1)	0.017 (1)	−0.012 (1)	−0.004 (1)
O6	0.023 (1)	0.049 (1)	0.038 (1)	0.003 (1)	0.008 (1)	−0.009 (1)
O7	0.032 (1)	0.028 (1)	0.029 (1)	0.007 (1)	0.004 (1)	0.004 (1)
O8	0.044 (1)	0.030 (1)	0.051 (1)	−0.013 (1)	0.015 (1)	−0.012 (1)
N1	0.019 (1)	0.019 (1)	0.018 (1)	−0.001 (1)	0.000 (1)	0.001 (1)
N2	0.020 (1)	0.022 (1)	0.017 (1)	−0.001 (1)	0.001 (1)	0.003 (1)
N3	0.019 (1)	0.023 (1)	0.021 (1)	−0.001 (1)	0.003 (1)	0.000 (1)
N4	0.022 (1)	0.019 (1)	0.017 (1)	0.000 (1)	0.001 (1)	−0.001 (1)
N5	0.019 (1)	0.019 (1)	0.017 (1)	0.000 (1)	0.001 (1)	−0.001 (1)
N6	0.020 (1)	0.019 (1)	0.018 (1)	0.000 (1)	0.002 (1)	0.000 (1)
C1	0.025 (1)	0.020 (1)	0.025 (1)	−0.004 (1)	0.003 (1)	0.004 (1)
C2	0.026 (1)	0.022 (1)	0.021 (1)	−0.001 (1)	0.002 (1)	0.006 (1)
C3	0.021 (1)	0.030 (1)	0.024 (1)	−0.003 (1)	0.003 (1)	0.000 (1)
C4	0.020 (1)	0.039 (2)	0.025 (1)	−0.001 (1)	0.003 (1)	0.008 (1)
C5	0.025 (1)	0.034 (2)	0.028 (1)	0.010 (1)	0.009 (1)	0.014 (1)
C6	0.030 (1)	0.023 (1)	0.022 (1)	0.006 (1)	0.008 (1)	0.008 (1)
C7	0.025 (1)	0.021 (1)	0.016 (1)	0.001 (1)	0.004 (1)	0.003 (1)
C8	0.027 (1)	0.019 (1)	0.024 (1)	0.001 (1)	0.002 (1)	−0.002 (1)
C9	0.025 (1)	0.020 (1)	0.021 (1)	−0.003 (1)	0.005 (1)	−0.003 (1)
C10	0.027 (1)	0.022 (1)	0.020 (1)	0.003 (1)	0.006 (1)	0.001 (1)
C11	0.025 (1)	0.026 (1)	0.019 (1)	0.005 (1)	−0.001 (1)	−0.002 (1)
C12	0.021 (1)	0.023 (1)	0.024 (1)	0.002 (1)	−0.001 (1)	−0.004 (1)
C13	0.017 (1)	0.019 (1)	0.020 (1)	0.002 (1)	0.001 (1)	−0.001 (1)
C14	0.020 (1)	0.021 (1)	0.023 (1)	−0.004 (1)	−0.002 (1)	−0.001 (1)
C15	0.021 (1)	0.017 (1)	0.019 (1)	0.001 (1)	0.005 (1)	−0.003 (1)
C16	0.020 (1)	0.020 (1)	0.024 (1)	0.000 (1)	0.005 (1)	−0.005 (1)
C17	0.021 (1)	0.026 (1)	0.026 (1)	−0.001 (1)	−0.001 (1)	−0.007 (1)
C18	0.022 (1)	0.030 (1)	0.018 (1)	0.002 (1)	−0.003 (1)	−0.002 (1)
C19	0.020 (1)	0.023 (1)	0.018 (1)	0.000 (1)	0.002 (1)	−0.001 (1)
C20	0.023 (1)	0.025 (1)	0.019 (1)	0.001 (1)	−0.003 (1)	0.004 (1)
C21	0.026 (1)	0.021 (1)	0.020 (1)	0.000 (1)	0.000 (1)	0.001 (1)
C22	0.026 (1)	0.021 (1)	0.031 (1)	0.006 (1)	0.002 (1)	0.002 (1)
C23	0.026 (1)	0.024 (1)	0.034 (2)	0.005 (1)	0.009 (1)	0.000 (1)
C24	0.030 (1)	0.020 (1)	0.026 (1)	0.000 (1)	0.009 (1)	0.000 (1)
C25	0.023 (1)	0.017 (1)	0.021 (1)	−0.003 (1)	0.003 (1)	−0.002 (1)
C26	0.024 (1)	0.028 (1)	0.019 (1)	0.000 (1)	0.005 (1)	0.002 (1)
C27	0.026 (1)	0.021 (1)	0.030 (1)	−0.003 (1)	0.005 (1)	−0.007 (1)
C28	0.036 (2)	0.017 (1)	0.031 (1)	−0.001 (1)	0.011 (1)	−0.002 (1)
C29	0.038 (2)	0.021 (1)	0.021 (1)	0.004 (1)	0.004 (1)	0.000 (1)
C30	0.028 (1)	0.019 (1)	0.021 (1)	0.001 (1)	0.002 (1)	−0.003 (1)

Geometric parameters (Å, º)

Zn1—N1	2.189 (2)	C15—C30	1.415 (4)
Zn1—N2	2.229 (2)	C16—C27	1.416 (4)
Zn1—N3	2.182 (2)	C16—C17	1.419 (4)
Zn1—N4	2.181 (2)	C17—C18	1.360 (4)
Zn1—N5	2.138 (2)	C18—C19	1.412 (4)
Zn1—N6	2.131 (2)	C19—C20	1.514 (4)
Cl1—O1	1.419 (2)	C21—C22	1.376 (4)
Cl1—O2	1.419 (1)	C22—C23	1.386 (4)
Cl1—O3	1.419 (1)	C23—C24	1.375 (4)
Cl1—O4	1.419 (1)	C24—C25	1.388 (4)
Cl1'—O1'	1.419 (2)	C25—C26	1.514 (4)
Cl1'—O2'	1.419 (1)	C27—C28	1.370 (4)
Cl1'—O3'	1.419 (1)	C28—C29	1.404 (4)
Cl1'—O4'	1.419 (1)	C29—C30	1.371 (4)
Cl2—O5	1.432 (2)	C1—H1a	0.95
Cl2—O6	1.439 (2)	C1—H1b	0.95
Cl2—O7	1.442 (2)	C2—H2a	0.95
Cl2—O8	1.433 (2)	C2—H2b	0.95
N1—C1	1.476 (3)	C3—H3	0.95
N1—C8	1.480 (3)	C4—H4	0.95
N1—C14	1.474 (3)	C5—H5	0.95
N2—C2	1.484 (3)	C6—H6	0.95
N2—C20	1.469 (3)	C8—H8a	0.95
N2—C26	1.480 (3)	C8—H8b	0.95
N3—C3	1.349 (3)	C9—H9	0.95
N3—C7	1.342 (3)	C10—H10	0.95
N4—C9	1.347 (3)	C11—H11	0.95
N4—C13	1.349 (3)	C12—H12	0.95
N5—C15	1.374 (3)	C14—H14a	0.95
N5—C19	1.331 (3)	C14—H14b	0.95
N6—C21	1.349 (3)	C17—H17	0.95
N6—C25	1.343 (3)	C18—H18	0.95
C1—C2	1.525 (4)	C20—H20a	0.95
C3—C4	1.377 (4)	C20—H20b	0.95
C4—C5	1.382 (4)	C21—H21	0.95
C5—C6	1.381 (4)	C22—H22	0.95
C6—C7	1.394 (4)	C23—H23	0.95
C7—C8	1.508 (4)	C24—H24	0.95
C9—C10	1.380 (4)	C26—H26a	0.95
C10—C11	1.384 (4)	C26—H26b	0.95
C11—C12	1.378 (4)	C27—H27	0.95
C12—C13	1.392 (3)	C28—H28	0.95
C13—C14	1.514 (4)	C29—H29	0.95
C15—C16	1.415 (4)	C30—H30	0.95
N1—Zn1—N2	81.96 (8)	N5—C19—C18	122.2 (2)
N1—Zn1—N3	79.40 (8)	N5—C19—C20	117.9 (2)
N1—Zn1—N4	77.10 (8)	C18—C19—C20	119.8 (2)
N1—Zn1—N5	156.04 (8)	N2—C20—C19	111.1 (2)
N1—Zn1—N6	95.70 (8)	N6—C21—C22	122.5 (2)
N2—Zn1—N3	91.57 (8)	C21—C22—C23	118.8 (2)
N2—Zn1—N4	157.43 (8)	C22—C23—C24	119.1 (2)
N2—Zn1—N5	77.16 (8)	C23—C24—C25	119.4 (2)
N2—Zn1—N6	80.01 (8)	N6—C25—C24	121.6 (2)
N3—Zn1—N4	92.77 (8)	N6—C25—C26	118.8 (2)
N3—Zn1—N5	89.47 (8)	C24—C25—C26	119.5 (2)
N3—Zn1—N6	170.83 (8)	N2—C26—C25	115.2 (2)
N4—Zn1—N5	125.00 (8)	C16—C27—C28	120.4 (2)
N4—Zn1—N6	93.69 (8)	C27—C28—C29	120.2 (2)
N5—Zn1—N6	92.16 (8)	C28—C29—C30	120.9 (2)
Zn1—N1—C1	106.2 (1)	C15—C30—C29	119.9 (2)
Zn1—N1—C8	109.8 (2)	H1a—C1—H1b	109.4
Zn1—N1—C14	104.3 (1)	N1—C1—H1b	109.1
Zn1—N2—C2	105.2 (1)	C2—C1—H1b	109.2
Zn1—N2—C20	105.1 (1)	N1—C1—H1a	109.1
Zn1—N2—C26	109.2 (1)	C2—C1—H1a	109.2
Zn1—N3—C3	127.3 (2)	H2a—C2—H2b	109.4
Zn1—N3—C7	114.3 (2)	N2—C2—H2a	109.4
Zn1—N4—C9	130.2 (2)	C1—C2—H2a	109.4
Zn1—N4—C13	111.7 (2)	N2—C2—H2b	109.4
Zn1—N5—C15	126.3 (2)	C1—C2—H2b	109.3
Zn1—N5—C19	113.8 (2)	N3—C3—H3	118.4
Zn1—N6—C21	125.8 (2)	C4—C3—H3	118.3
Zn1—N6—C25	115.6 (2)	C3—C4—H4	120.9
O1—Cl1—O2	109.47 (2)	C5—C4—H4	120.8
O1—Cl1—O3	109.47 (2)	C6—C5—H5	120.3
O1—Cl1—O4	109.47 (2)	C4—C5—H5	120.4
O2—Cl1—O3	109.47 (1)	C5—C6—H6	120.4
O2—Cl1—O4	109.47 (1)	C7—C6—H6	120.3
O3—Cl1—O4	109.47 (6)	H8a—C8—H8b	109.4
O1'—Cl1'—O2'	109.47 (2)	N1—C8—H8b	108.2
O1'—Cl1'—O3'	109.47 (2)	C7—C8—H8b	108.2
O1'—Cl1'—O4'	109.47 (2)	N1—C8—H8a	108.2
O2'—Cl1'—O3'	109.47 (1)	C7—C8—H8a	108.2
O2'—Cl1'—O4'	109.47 (1)	N4—C9—H9	118.5
O3'—Cl1'—O4'	109.47 (6)	C10—C9—H9	118.5
O5—Cl2—O6	109.5 (1)	C9—C10—H10	120.6
O5—Cl2—O7	108.8 (1)	C11—C10—H10	120.7
O5—Cl2—O8	110.7 (1)	C12—C11—H11	120.5
O6—Cl2—O7	109.3 (1)	C10—C11—H11	120.5
O6—Cl2—O8	109.6 (1)	C11—C12—H12	120.3
O7—Cl2—O8	108.9 (1)	C13—C12—H12	120.2
C1—N1—C8	112.6 (2)	H14a—C14—H14b	109.4
C1—N1—C14	113.3 (2)	N1—C14—H14a	109.6
C8—N1—C14	110.3 (2)	C13—C14—H14a	109.6
C2—N2—C20	113.9 (2)	N1—C14—H14b	109.5
C2—N2—C26	112.4 (2)	C13—C14—H14b	109.4
C20—N2—C26	110.6 (2)	C18—C17—H17	120.1
C3—N3—C7	118.3 (2)	C16—C17—H17	120.0
C9—N4—C13	118.2 (2)	C17—C18—H18	120.2
C15—N5—C19	118.9 (2)	C19—C18—H18	120.1
C21—N6—C25	118.6 (2)	H20a—C20—H20b	109.4
N1—C1—C2	110.7 (2)	N2—C20—H20a	109.2
N2—C2—C1	109.9 (2)	C19—C20—H20a	109.0
N3—C3—C4	123.3 (3)	N2—C20—H20b	109.1
C3—C4—C5	118.3 (3)	C19—C20—H20b	109.0
C4—C5—C6	119.3 (3)	N6—C21—H21	118.7
C5—C6—C7	119.3 (3)	C22—C21—H21	118.8
N3—C7—C6	121.5 (2)	C21—C22—H22	120.4
N3—C7—C8	118.3 (2)	C23—C22—H22	120.8
C6—C7—C8	120.2 (2)	C24—C23—H23	120.5
N1—C8—C7	114.6 (2)	C22—C23—H23	120.5
N4—C9—C10	123.0 (2)	C23—C24—H24	120.4
C9—C10—C11	118.6 (2)	C25—C24—H24	120.2
C10—C11—C12	119.1 (2)	H26a—C26—H26b	109.3
C11—C12—C13	119.5 (2)	N2—C26—H26b	108.2
N4—C13—C12	121.6 (2)	C25—C26—H26b	108.0
N4—C13—C14	117.2 (2)	N2—C26—H26a	108.1
C12—C13—C14	121.2 (2)	C25—C26—H26a	108.0
N1—C14—C13	109.3 (2)	C28—C27—H27	119.7
N5—C15—C16	121.9 (2)	C16—C27—H27	119.9
N5—C15—C30	118.8 (2)	C27—C28—H28	119.8
C16—C15—C30	119.3 (2)	C29—C28—H28	120.0
C15—C16—C27	119.1 (2)	C30—C29—H29	119.5
C15—C16—C17	117.3 (2)	C28—C29—H29	119.6
C17—C16—C27	123.6 (2)	C29—C30—H30	120.1
C16—C17—C18	119.9 (2)	C15—C30—H30	120.0
C17—C18—C19	119.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1′^i	0.95	2.51	3.194 (4)	129
C17—H17···O7	0.95	2.55	3.448 (3)	157
C18—H18···O4′	0.95	2.54	3.209 (3)	128
C20—H20a···O7^ii	0.95	2.55	3.276 (3)	134
C21—H21···O8^iii	0.95	2.49	3.266 (3)	139
C27—H27···O5	0.95	2.43	3.053 (3)	123
C3—H3···Cg5	0.95	2.85	3.639 (3)	141
C29—H29···Cg3^iv	0.95	2.79	3.538 (3)	136

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y−1/2, z+1/2; (iv) −x+1, −y, −z+2.

(III) [N,N'-bis(2-pyridylmethyl)-N,N'-bis(2-quinolmethyl)ethane-1,2-diamine-κ⁶N]- zinc(II) diperchlorate monohydrate

Crystal data

[Zn(C34H32N6)](ClO4)2·H2O	F(000) = 1664
Mr = 806.99	Dx = 1.573 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8135 reflections
a = 11.891 (3) Å	θ = 1.9–29.7°
b = 12.022 (3) Å	µ = 0.94 mm^−1
c = 23.838 (5) Å	T = 120 K
V = 3407.8 (14) Å^3	Block, colourless
Z = 4	0.54 × 0.38 × 0.30 mm

Data collection

Siemens SMART CCD area-detector diffractometer	7803 independent reflections
Radiation source: x-ray tube	6872 reflections with I > 2.5σ(I)
Graphite monochromator	Rint = 0.064
ω rotation scans with narrow frames	θmax = 27.5°, θmin = 1.9°
Absorption correction: integration (XPREP; Siemens, 1995)	h = −15→15
Tmin = 0.664, Tmax = 0.774	k = −15→15
28487 measured reflections	l = −24→30

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/{[σcs(F^2) + B + (1 + A)F^2]^1/2-|F|}^2 where A = 0.03 and B = 0.51
wR(F^2) = 0.038	(Δ/σ)max = 0.006
S = 1.00	Δρmax = 1.15 (9) e Å^−3
6872 reflections	Δρmin = −0.59 (9) e Å^−3
470 parameters	Absolute structure: Rogers factor refined for 2959 Bijvoet pairs where both members have I > 3σ(I) For the crystal studied, N1 and N2 have the S configuration
0 restraints	Rogers parameter: 0.93 (2)

Special details

Refinement. Sfls: F calc weight full matrix

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.34767 (3)	0.90694 (3)	0.64272 (1)	0.0220 (1)
Cl1	−0.01330 (7)	0.18957 (6)	0.53900 (3)	0.0296 (4)
Cl2	−0.14471 (9)	0.66346 (8)	0.63062 (3)	0.0469 (5)
O1	−0.0131 (2)	0.1406 (2)	0.5940 (1)	0.039 (1)
O2	−0.1191 (2)	0.1693 (2)	0.5115 (1)	0.042 (1)
O3	0.0035 (3)	0.3083 (2)	0.5441 (1)	0.069 (2)
O4	0.0760 (2)	0.1426 (2)	0.5066 (1)	0.046 (1)
O5	−0.0618 (2)	0.6516 (3)	0.6743 (1)	0.063 (2)
O6	−0.1735 (4)	0.5589 (2)	0.6069 (1)	0.094 (3)
O7	−0.2457 (3)	0.7122 (4)	0.6558 (1)	0.090 (3)
O8	−0.1056 (3)	0.7368 (2)	0.5880 (1)	0.058 (2)
O9	0.0754 (3)	0.4863 (3)	0.6044 (2)	0.098 (3)
N1	0.3494 (2)	0.9623 (2)	0.5545 (1)	0.028 (1)
N2	0.1809 (2)	0.8480 (2)	0.6149 (1)	0.028 (1)
N3	0.2940 (2)	1.0734 (2)	0.6553 (1)	0.024 (1)
N4	0.5234 (2)	0.9624 (2)	0.6291 (1)	0.026 (1)
N5	0.2633 (2)	0.8509 (2)	0.7207 (1)	0.023 (1)
N6	0.3915 (2)	0.7409 (2)	0.6222 (1)	0.028 (1)
C1	0.2576 (3)	0.9044 (3)	0.5244 (1)	0.036 (2)
C2	0.1546 (3)	0.9019 (3)	0.5610 (1)	0.032 (1)
C3	0.2599 (2)	1.1198 (2)	0.7036 (1)	0.027 (2)
C4	0.2200 (3)	1.2268 (3)	0.7072 (1)	0.032 (2)
C5	0.2135 (3)	1.2883 (2)	0.6580 (1)	0.033 (2)
C6	0.2484 (3)	1.2431 (2)	0.6081 (1)	0.028 (2)
C7	0.2897 (2)	1.1339 (2)	0.6079 (1)	0.024 (1)
C8	0.3347 (3)	1.0855 (3)	0.5542 (1)	0.030 (1)
C9	0.6073 (3)	0.9875 (2)	0.6674 (1)	0.025 (1)
C10	0.7217 (3)	0.9980 (2)	0.6511 (1)	0.033 (2)
C11	0.7477 (3)	0.9877 (3)	0.5936 (2)	0.045 (2)
C12	0.6637 (3)	0.9702 (3)	0.5564 (1)	0.042 (2)
C13	0.5524 (3)	0.9570 (3)	0.5751 (1)	0.030 (2)
C14	0.4617 (3)	0.9317 (3)	0.5328 (1)	0.034 (2)
C15	0.3089 (2)	0.8255 (2)	0.7719 (1)	0.024 (1)
C16	0.2416 (3)	0.8177 (2)	0.8211 (1)	0.030 (2)
C17	0.1250 (3)	0.8307 (3)	0.8149 (1)	0.039 (2)
C18	0.0797 (3)	0.8480 (3)	0.7630 (1)	0.038 (2)
C19	0.1510 (3)	0.8586 (2)	0.7165 (1)	0.028 (1)
C20	0.1025 (3)	0.8815 (2)	0.6596 (1)	0.030 (2)
C21	0.4961 (3)	0.6962 (3)	0.6216 (1)	0.034 (2)
C22	0.5174 (3)	0.5904 (3)	0.6021 (1)	0.039 (2)
C23	0.4290 (4)	0.5278 (3)	0.5829 (1)	0.046 (2)
C24	0.3210 (3)	0.5700 (3)	0.5840 (1)	0.038 (2)
C25	0.3041 (3)	0.6785 (3)	0.6048 (1)	0.031 (2)
C26	0.1870 (3)	0.7247 (2)	0.6101 (1)	0.033 (2)
C27	0.2937 (3)	0.7944 (3)	0.8728 (1)	0.036 (2)
C28	0.4064 (3)	0.7766 (3)	0.8756 (1)	0.036 (2)
C29	0.4729 (3)	0.7802 (2)	0.8269 (1)	0.032 (2)
C30	0.4256 (3)	0.8045 (2)	0.7763 (1)	0.028 (2)
C31	0.8035 (3)	1.0221 (3)	0.6929 (2)	0.038 (2)
C32	0.7733 (3)	1.0346 (3)	0.7475 (1)	0.036 (2)
C33	0.6599 (3)	1.0269 (2)	0.7630 (1)	0.033 (2)
C34	0.5787 (3)	1.0049 (2)	0.7241 (1)	0.027 (2)
H91	0.0330	0.4263	0.5883	0.100*
H92	0.0117	0.5266	0.6205	0.100*
H1a	0.2411	0.9428	0.4906	0.043*
H1b	0.2801	0.8304	0.5159	0.043*
H2a	0.0968	0.8613	0.5425	0.039*
H2b	0.1298	0.9758	0.5676	0.039*
H3	0.2635	1.0765	0.7369	0.032*
H4	0.1977	1.2577	0.7421	0.038*
H5	0.1847	1.3621	0.6589	0.039*
H6	0.2445	1.2849	0.5743	0.033*
H8a	0.4059	1.1184	0.5469	0.036*
H8b	0.2841	1.1040	0.5248	0.036*
H11	0.8233	0.9929	0.5812	0.054*
H12	0.6800	0.9668	0.5175	0.050*
H14a	0.4627	0.8543	0.5247	0.041*
H14b	0.4760	0.9726	0.4995	0.041*
H17	0.0775	0.8275	0.8469	0.046*
H18	0.0005	0.8528	0.7584	0.045*
H20a	0.0876	0.9589	0.6563	0.037*
H20b	0.0343	0.8411	0.6555	0.037*
H21	0.5572	0.7396	0.6351	0.041*
H22	0.5917	0.5614	0.6019	0.047*
H23	0.4421	0.4549	0.5689	0.055*
H24	0.2593	0.5269	0.5709	0.046*
H26a	0.1535	0.6934	0.6427	0.040*
H26b	0.1454	0.7028	0.5779	0.040*
H27	0.2497	0.7910	0.9061	0.043*
H28	0.4407	0.7617	0.9108	0.043*
H29	0.5512	0.7655	0.8293	0.038*
H30	0.4715	0.8075	0.7437	0.033*
H31	0.8802	1.0296	0.6826	0.046*
H32	0.8290	1.0486	0.7751	0.043*
H33	0.6392	1.0371	0.8011	0.040*
H34	0.5022	1.0013	0.7353	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0254 (1)	0.0231 (1)	0.0175 (1)	0.0017 (1)	−0.0007 (1)	0.0002 (1)
Cl1	0.0334 (4)	0.0305 (4)	0.0249 (3)	0.0062 (3)	−0.0065 (3)	0.0009 (3)
Cl2	0.0551 (5)	0.0530 (5)	0.0326 (4)	−0.0194 (5)	−0.0010 (4)	−0.0058 (3)
O1	0.043 (1)	0.050 (1)	0.023 (1)	0.004 (1)	−0.002 (1)	0.002 (1)
O2	0.035 (1)	0.054 (1)	0.038 (1)	0.009 (1)	−0.014 (1)	−0.008 (1)
O3	0.097 (2)	0.028 (1)	0.083 (2)	0.004 (1)	−0.040 (2)	0.002 (1)
O4	0.039 (1)	0.071 (2)	0.027 (1)	0.015 (1)	0.004 (1)	0.010 (1)
O5	0.049 (2)	0.080 (2)	0.059 (2)	−0.012 (1)	−0.007 (1)	0.018 (2)
O6	0.176 (4)	0.045 (2)	0.060 (2)	−0.027 (2)	−0.033 (2)	0.002 (1)
O7	0.056 (2)	0.148 (4)	0.065 (2)	0.017 (2)	0.004 (2)	−0.006 (2)
O8	0.073 (2)	0.052 (2)	0.049 (2)	−0.014 (1)	−0.004 (1)	0.005 (1)
O9	0.084 (3)	0.069 (2)	0.142 (4)	0.001 (2)	−0.023 (3)	0.002 (2)
N1	0.036 (1)	0.030 (1)	0.019 (1)	0.004 (1)	−0.001 (1)	−0.001 (1)
N2	0.031 (1)	0.027 (1)	0.025 (1)	0.001 (1)	−0.007 (1)	0.002 (1)
N3	0.025 (1)	0.027 (1)	0.020 (1)	−0.002 (1)	0.003 (1)	−0.001 (1)
N4	0.031 (1)	0.027 (1)	0.019 (1)	0.005 (1)	0.003 (1)	0.001 (1)
N5	0.026 (1)	0.020 (1)	0.023 (1)	0.001 (1)	0.001 (1)	0.001 (1)
N6	0.036 (1)	0.029 (1)	0.020 (1)	0.007 (1)	−0.001 (1)	−0.002 (1)
C1	0.053 (2)	0.034 (2)	0.021 (1)	0.003 (2)	−0.012 (1)	0.001 (1)
C2	0.036 (2)	0.033 (1)	0.028 (1)	0.004 (2)	−0.013 (1)	0.003 (1)
C3	0.028 (2)	0.027 (2)	0.025 (1)	−0.003 (1)	0.004 (1)	−0.001 (1)
C4	0.032 (2)	0.031 (2)	0.033 (2)	0.000 (1)	0.007 (1)	−0.005 (1)
C5	0.033 (2)	0.023 (1)	0.041 (2)	−0.001 (1)	0.001 (1)	−0.002 (1)
C6	0.027 (2)	0.026 (1)	0.030 (2)	−0.003 (1)	−0.005 (1)	0.005 (1)
C7	0.023 (2)	0.023 (1)	0.026 (1)	0.000 (1)	−0.003 (1)	0.001 (1)
C8	0.039 (2)	0.031 (1)	0.021 (1)	0.002 (2)	0.000 (1)	0.002 (1)
C9	0.031 (2)	0.023 (1)	0.021 (1)	0.001 (1)	0.001 (1)	0.001 (1)
C10	0.035 (2)	0.030 (2)	0.034 (2)	0.001 (1)	0.003 (1)	0.005 (1)
C11	0.033 (2)	0.057 (2)	0.043 (2)	0.003 (2)	0.017 (2)	0.008 (2)
C12	0.044 (2)	0.055 (2)	0.027 (2)	0.000 (2)	0.018 (2)	0.000 (1)
C13	0.039 (2)	0.030 (2)	0.022 (1)	0.005 (1)	0.006 (1)	0.001 (1)
C14	0.047 (2)	0.038 (2)	0.017 (1)	0.011 (1)	0.002 (1)	0.000 (1)
C15	0.032 (2)	0.018 (1)	0.021 (1)	0.000 (1)	0.002 (1)	0.000 (1)
C16	0.042 (2)	0.024 (1)	0.025 (1)	−0.003 (1)	0.006 (1)	0.001 (1)
C17	0.036 (2)	0.047 (2)	0.033 (2)	0.002 (1)	0.015 (1)	0.003 (1)
C18	0.026 (2)	0.043 (2)	0.044 (2)	0.001 (1)	0.007 (1)	0.005 (2)
C19	0.029 (1)	0.023 (1)	0.031 (1)	0.001 (1)	−0.001 (1)	0.001 (1)
C20	0.028 (2)	0.029 (2)	0.035 (2)	0.001 (1)	−0.005 (1)	0.003 (1)
C21	0.038 (2)	0.038 (2)	0.027 (1)	0.014 (2)	0.004 (1)	0.001 (1)
C22	0.047 (2)	0.040 (2)	0.031 (2)	0.018 (2)	0.006 (1)	0.000 (2)
C23	0.075 (3)	0.035 (2)	0.027 (2)	0.020 (2)	−0.004 (2)	−0.007 (1)
C24	0.058 (2)	0.033 (2)	0.023 (1)	0.010 (1)	−0.014 (1)	−0.005 (1)
C25	0.046 (2)	0.028 (1)	0.018 (1)	0.005 (1)	−0.010 (1)	−0.003 (1)
C26	0.043 (2)	0.025 (1)	0.032 (2)	0.001 (1)	−0.012 (1)	−0.003 (1)
C27	0.054 (2)	0.036 (2)	0.019 (2)	−0.004 (2)	0.005 (1)	0.001 (1)
C28	0.055 (2)	0.031 (2)	0.022 (2)	−0.005 (2)	−0.009 (1)	0.001 (1)
C29	0.037 (2)	0.029 (2)	0.029 (2)	0.005 (1)	−0.007 (1)	0.000 (1)
C30	0.033 (2)	0.027 (1)	0.024 (1)	0.000 (1)	0.000 (1)	0.000 (1)
C31	0.028 (2)	0.035 (2)	0.051 (2)	−0.001 (1)	−0.002 (2)	0.006 (2)
C32	0.038 (2)	0.031 (2)	0.040 (2)	−0.005 (1)	−0.013 (2)	0.004 (1)
C33	0.044 (2)	0.028 (1)	0.028 (1)	−0.003 (2)	−0.003 (2)	−0.001 (1)
C34	0.031 (2)	0.027 (1)	0.023 (1)	0.002 (1)	0.001 (1)	0.002 (1)

Geometric parameters (Å, º)

Zn1—N1	2.205 (2)	C22—C23	1.371 (5)
Zn1—N2	2.208 (2)	C23—C24	1.382 (5)
Zn1—N3	2.122 (2)	C24—C25	1.410 (4)
Zn1—N4	2.217 (3)	C25—C26	1.505 (5)
Zn1—N5	2.217 (2)	C27—C16	1.407 (4)
Zn1—N6	2.121 (2)	C28—C27	1.359 (5)
Cl1—O1	1.437 (2)	C29—C28	1.405 (5)
Cl1—O2	1.440 (2)	C30—C29	1.364 (4)
Cl1—O3	1.447 (3)	C31—C10	1.422 (5)
Cl1—O4	1.429 (2)	C32—C31	1.357 (5)
Cl2—O5	1.441 (3)	C33—C32	1.401 (5)
Cl2—O6	1.421 (3)	C34—C33	1.365 (4)
Cl2—O8	1.423 (3)	O9—H91	0.96
Cl2—O7	1.465 (3)	O9—H92	0.98
N1—C1	1.481 (4)	C2—H2b	0.95
N1—C8	1.492 (4)	C2—H2a	0.95
N1—C14	1.478 (4)	C1—H1b	0.95
N2—C2	1.474 (4)	C1—H1a	0.95
N2—C20	1.473 (4)	C30—H30	0.95
N2—C26	1.489 (4)	C29—H29	0.95
N3—C3	1.342 (4)	C28—H28	0.95
N3—C7	1.346 (4)	C27—H27	0.95
N4—C9	1.385 (4)	C17—H17	0.95
N4—C13	1.336 (4)	C18—H18	0.95
N5—C15	1.371 (4)	C20—H20a	0.95
N5—C19	1.343 (4)	C20—H20b	0.95
N6—C21	1.355 (4)	C21—H21	0.95
N6—C25	1.347 (4)	C22—H22	0.95
C1—C2	1.504 (5)	C23—H23	0.95
C3—C4	1.374 (4)	C24—H24	0.95
C4—C5	1.388 (4)	C26—H26a	0.95
C5—C6	1.374 (4)	C26—H26b	0.95
C6—C7	1.401 (4)	C34—H34	0.95
C7—C8	1.505 (4)	C33—H33	0.95
C9—C10	1.420 (4)	C32—H32	0.95
C9—C34	1.410 (4)	C31—H31	0.95
C10—C11	1.411 (5)	C11—H11	0.95
C11—C12	1.352 (5)	C12—H12	0.95
C12—C13	1.404 (5)	C14—H14b	0.95
C13—C14	1.507 (4)	C14—H14a	0.95
C15—C30	1.415 (4)	C3—H3	0.95
C15—C16	1.423 (4)	C4—H4	0.95
C16—C17	1.404 (5)	C5—H5	0.95
C17—C18	1.366 (5)	C6—H6	0.95
C18—C19	1.401 (4)	C8—H8b	0.95
C19—C20	1.499 (4)	C8—H8a	0.95
C21—C22	1.378 (5)
N1—Zn1—N2	79.6 (1)	C9—C10—C31	118.8 (3)
N1—Zn1—N3	81.57 (9)	C31—C10—C11	123.3 (3)
N1—Zn1—N4	76.18 (9)	C10—C11—C12	119.3 (3)
N1—Zn1—N5	153.5 (1)	C11—C12—C13	120.4 (3)
N1—Zn1—N6	93.57 (9)	C12—C13—C14	119.1 (3)
N2—Zn1—N3	94.32 (9)	C30—C15—C16	118.7 (3)
N2—Zn1—N4	154.04 (9)	C15—C16—C17	117.5 (3)
N2—Zn1—N5	75.40 (9)	C27—C16—C17	123.3 (3)
N2—Zn1—N6	81.3 (1)	C15—C16—C27	119.2 (3)
N3—Zn1—N4	91.16 (9)	C16—C17—C18	120.1 (3)
N3—Zn1—N5	91.81 (8)	C17—C18—C19	119.5 (3)
N3—Zn1—N6	174.03 (9)	C18—C19—C20	120.0 (3)
N4—Zn1—N5	129.82 (8)	C21—C22—C23	118.6 (3)
N4—Zn1—N6	91.04 (9)	C22—C23—C24	120.3 (3)
N5—Zn1—N6	91.04 (9)	C23—C24—C25	118.6 (3)
Zn1—N1—C1	108.3 (2)	C24—C25—C26	120.2 (3)
Zn1—N1—C2	80.9 (1)	C28—C27—C16	120.5 (3)
Zn1—N1—C8	107.7 (2)	C29—C28—C27	120.6 (3)
Zn1—N1—C13	79.2 (1)	C30—C29—C28	120.4 (3)
Zn1—N1—C14	105.5 (2)	C15—C30—C29	120.5 (3)
Zn1—N2—C1	80.8 (1)	C32—C31—C10	120.9 (3)
Zn1—N2—C2	108.2 (2)	C33—C32—C31	120.0 (3)
Zn1—N2—C26	107.4 (2)	C34—C33—C32	121.0 (3)
Zn1—N2—C19	79.5 (1)	C9—C34—C33	120.7 (3)
Zn1—N2—C20	105.3 (2)	H91—O9—H92	97.0
Zn1—N3—C3	127.2 (2)	H2a—C2—H2b	109.5
Zn1—N3—C4	155.8 (1)	N2—C2—H2b	109.4
Zn1—N3—C6	143.7 (1)	C1—C2—H2b	109.4
Zn1—N3—C7	113.7 (2)	N2—C2—H2a	109.3
Zn1—N3—C8	81.8 (1)	C1—C2—H2a	109.3
Zn1—N4—C9	130.5 (2)	H1a—C1—H1b	109.5
Zn1—N4—C12	140.3 (1)	N1—C1—H1b	109.6
Zn1—N4—C10	158.0 (1)	C2—C1—H1b	109.6
Zn1—N4—C14	78.9 (1)	N1—C1—H1a	109.6
Zn1—N4—C34	100.6 (1)	C2—C1—H1a	109.5
Zn1—N5—C19	111.5 (2)	C29—C30—H30	119.7
Zn1—N5—C15	129.5 (2)	C15—C30—H30	119.8
Zn1—N5—C18	140.1 (1)	C30—C29—H29	119.8
Zn1—N5—C30	99.7 (1)	C28—C29—H29	119.8
Zn1—N5—C20	78.9 (1)	C27—C28—H28	119.7
Zn1—N5—C16	156.9 (1)	C29—C28—H28	119.6
Zn1—N6—C21	127.0 (2)	C28—C27—H27	119.7
Zn1—N4—C13	111.7 (2)	C16—C27—H27	119.8
Zn1—N6—C22	155.6 (2)	C18—C17—H17	120.0
Zn1—N6—C24	143.9 (1)	C16—C17—H17	119.9
Zn1—N6—C25	113.9 (2)	C17—C18—H18	120.2
Zn1—N6—C26	81.9 (1)	C19—C18—H18	120.2
O1—Cl1—O2	110.4 (2)	H20a—C20—H20b	109.5
O1—Cl1—O3	109.1 (2)	N2—C20—H20a	109.1
O1—Cl1—O4	109.2 (1)	C19—C20—H20a	109.1
O2—Cl1—O3	109.0 (2)	N2—C20—H20b	109.0
O2—Cl1—O4	109.7 (1)	C19—C20—H20b	109.0
O3—Cl1—O4	109.4 (2)	N6—C21—H21	118.7
O5—Cl2—O6	111.4 (2)	C22—C21—H21	118.7
O5—Cl2—O7	107.7 (2)	C23—C22—H22	120.7
O5—Cl2—O8	110.7 (2)	C21—C22—H22	120.7
O6—Cl2—O7	108.6 (3)	C22—C23—H23	119.8
O6—Cl2—O8	110.0 (2)	C24—C23—H23	119.9
O7—Cl2—O8	108.2 (2)	C23—C24—H24	120.7
C1—N1—C8	112.2 (2)	C25—C24—H24	120.7
C1—N1—C14	112.3 (2)	H26a—C26—H26b	109.5
C14—N1—C8	110.5 (2)	N2—C26—H26a	108.1
C2—N2—C20	112.1 (2)	C25—C26—H26a	108.2
C2—N2—C26	112.5 (2)	N2—C26—H26b	108.2
C20—N2—C26	111.0 (2)	C25—C26—H26b	108.1
C3—N3—C7	119.0 (2)	C33—C34—H34	119.7
C9—N4—C13	117.3 (3)	C9—C34—H34	119.6
C15—N5—C19	118.4 (2)	C34—C33—H33	119.5
C21—N6—C25	119.0 (3)	C32—C33—H33	119.6
N1—C1—C2	109.2 (2)	C31—C32—H32	120.0
N1—C8—C7	114.9 (2)	C33—C32—H32	120.0
N1—C14—C13	111.3 (2)	C32—C31—H31	119.5
N2—C2—C1	109.9 (2)	C10—C31—H31	119.6
N2—C20—C19	111.2 (2)	C12—C11—H11	120.4
N2—C26—C25	114.7 (3)	C10—C11—H11	120.3
N3—C3—C4	123.1 (3)	C11—C12—H12	119.8
N3—C7—C6	121.1 (3)	C13—C12—H12	119.8
N3—C7—C8	119.5 (2)	H14a—C14—H14b	109.4
N4—C9—C10	122.1 (3)	N1—C14—H14b	109.1
N4—C9—C34	119.3 (3)	C13—C14—H14b	109.0
N4—C13—C12	122.9 (3)	N1—C14—H14a	109.0
N4—C13—C14	118.0 (3)	C13—C14—H14a	109.0
N5—C15—C16	121.8 (3)	N3—C3—H3	118.4
N5—C15—C30	119.5 (3)	C4—C3—H3	118.5
N5—C19—C18	122.4 (3)	C3—C4—H4	121.1
N5—C19—C20	117.6 (3)	C5—C4—H4	121.1
N6—C21—C22	122.6 (3)	C6—C5—H5	119.9
N6—C25—C24	120.9 (3)	C4—C5—H5	119.9
N6—C25—C26	118.9 (3)	C5—C6—H6	120.7
C3—C4—C5	117.8 (3)	C7—C6—H6	120.6
C4—C5—C6	120.2 (3)	H8a—C8—H8b	109.4
C5—C6—C7	118.7 (3)	N1—C8—H8b	108.1
C6—C7—C8	119.3 (3)	C7—C8—H8b	108.1
C34—C9—C10	118.6 (3)	N1—C8—H8a	108.1
C9—C10—C11	117.8 (3)	C7—C8—H8a	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H91···O3	0.96	1.80	2.716 (5)	158
O9—H92···O5	0.98	2.16	3.064 (5)	153
O9—H92···O6	0.98	2.26	3.086 (6)	142
C1—H1a···O6^i	0.95	2.54	3.265 (4)	134
C2—H2b···O4^ii	0.95	2.56	3.306 (4)	136
C4—H4···O7^iii	0.95	2.56	3.285 (3)	133
C5—H5···O9^ii	0.95	2.37	3.162 (5)	141
C8—H8b···O4^ii	0.95	2.55	3.350 (4)	141
C20—H20b···O5	0.95	2.59	3.403 (4)	144
C21—H21···O7^iv	0.95	2.42	3.183 (5)	137
C23—H23···O2^v	0.95	2.54	3.318 (4)	140
C24—H24···O9	0.95	2.38	3.127 (5)	135
C28—H28···O4^vi	0.95	2.56	3.277 (4)	132
C29—H29···Cg3^vii	0.95	2.55	3.479 (4)	166
C33—H33···Cg9^viii	0.95	2.63	3.544 (3)	161

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x, y+1, z; (iii) −x, y+1/2, −z+3/2; (iv) x+1, y, z; (v) x+1/2, −y+1/2, −z+1; (vi) −x+1/2, −y+1, z+1/2; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+1, y+1/2, −z+3/2.