Crystal structures of zinc(II) coordination complexes with iso­quinoline N-oxide

Groneck, E.N.; Peek, N.; Lynch, W.E.; Padgett, C.W.

doi:10.1107/S2056989025000180

research communications

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ISSN: 2056-9890

Volume 81| Part 2| February 2025| Pages 132-139

https://doi.org/10.1107/S2056989025000180

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Crystal structures of zinc(II) coordination complexes with isoquinoline N-oxide

Erin N. Groneck,^a Nathan Peek,^a Will E. Lynch ^a and Clifford W. Padgett ^a ^*

^aDepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, Armstrong Campus, 11935 Abercorn Street, Savannah GA 31419, USA
^*Correspondence e-mail: cpadgett@georgiasouthern.edu

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 31 December 2024; accepted 8 January 2025; online 14 January 2025)

The reaction of one equivalent of zinc(II) halide salts with two equivalents of isoquinoline N-oxide (iQNO; C₉H₇NO) in methanol yields compounds of the general formula [ZnX₂(iQNO)₂], with X = Cl⁻ (I), Br⁻ (II) and I⁻ (III). However, starting with zinc(II) perchlorate or nitrate leads to the formation of complex ions with the compositions [Zn(iQNO)₆](X)₂ for X = ClO₄⁻ (IV), and [Zn(iQNO)(H₂O)₅](iQNO)₂X₂ for X = NO₃⁻ (V). Complexes (I), (II) and (III), namely dichloridobis(isoquinoline N-oxide-κO)zinc(II) [ZnCl₂(C₉H₇NO)₂], dibromidobis(isoquinoline N-oxide-κO)zinc(II) [ZnBr₂(C₉H₇NO)₂], and diiodidobis(isoquinoline N-oxide-κO)zinc(II) [ZnI₂(C₉H₇NO)₂], each exhibit a distorted tetrahedral coordination geometry around the zinc(II) ion coordinated by two iQNO ligands bound through the oxygen atom and two halide ions. The zinc ion lies on a crystallographic twofold axis in the bromo complex. The X—Zn—X bond angles are approximately 15–17° larger than the O—Zn—O bond angles resulting in the observed tetrahedral distortion. In complex (IV), hexakis(isoquinoline N-oxide-κO)zinc(II) bis(perchlorate), [Zn(C₉H₇NO)₆](ClO₄)₂, the zinc(II) ion occupies a special position with 3 site symmetry and is octahedrally coordinated by six iQNO ligands, albeit with slight distortions evidenced by a spread of cis bond angles from 85.82 (4) to 94.18 (4)°. The chlorine atom of the perchlorate anion lies on a crystallographic threefold axis. Finally, complex (V) crystallizes with a pseudo-octahedral geometry; pentaaqua(isoquinoline N-oxide-κO)zinc(II) dinitrate–isoquinoline N-oxide (1/2), [Zn(C₉H₇NO)(H₂O)₅](NO₃)₂·2(C₉H₇NO). The nitrate ions and non-coordinated iQNO molecules engage in π-stacking and hydrogen-bonding interactions with the coordinated water molecules. The iQNO—Zn—O equatorial bond angles range from 88.98 (9) to 94.90 (9)°, with the largest deviation from a perfect octahedral angle attributed to the influence of a weak C—H⋯O (from water) interaction (2.287 Å) involving the bound iQNO ligand.

Keywords: crystal structure; zinc(II) coordination complex; isoquinoline N-oxide; Hirshfeld surface analysis.

CCDC references: 2415566; 2415565; 2415564; 2415563; 2415562

1. Chemical context

There is a great deal of interest in the chemistry of N-oxides due to their ubiquity in nature, recent advances in pharmaceutical chemistry (see, for example, Kobus et al., 2024 ), and their important roles in synthesis and materials science (e.g., Ang et al., 2024 ; Larin & Fershtat, 2022 ). Functional features of importance include the highly polar N—O bond, which is capable of forming strong interactions with cations. Aromatic N-oxides are more stable and have a slightly higher bond order than their aliphatic counterparts, as they allow for back-donation of electron density into the π* orbital (Lukomska et al., 2015 ; Greenberg et al., 2020 ). Recently, the effect of isoquinolinequinone N-oxides as potent anticancer agents has also been reported (Kruschel et al., 2024 ).

Transformations involving N-oxides and transition metals include both the synthesis and reactivity of these complexes (see, for example, Eppenson, 2003 ; Moustafa et al., 2014 ). These transformations take advantage of the Lewis acid/base properties of metals and the polar N-oxide ligands. Owing to this, there is considerable interest in metal complexes that bind N-oxides and their structures. We have previously reported the structures of zinc(II) halide complexes with quinoline N-oxide (QNO) (Padgett et al., 2022 ). In the present study, we extend our work on QNO zinc complexes to isoquinoline N-oxide (iQNO) complexes. Herein, we report five iQNO/zinc(II) complexes containing chloride, bromide, iodide, perchlorate, and nitrate anions.

The three zinc(II) halide complexes can be formulated as mononuclear Zn(X)₂(iQNO)₂ species in a distorted tetrahedral environment. The non-coordinating perchlorate and nitrate derivatives yield significantly different complexes. The perchlorate complex is hexacoordinated, with six iQNO molecules bound to the metal ion in a pseudo-octahedral environment, formulated as [Zn(iQNO)₆](ClO₄)₂. The nitrate derivative is also six-coordinate but features five water molecules and one iQNO ligand in the coordination sphere, with two π-stacked iQNOs and two nitrate anions present in the structure.

2. Structural commentary

Compound (I) crystallizes in the triclinic space group P $[\overline{1}]$ (Fig. 1) and exhibits a distorted tetrahedral coordination environment around the Zn center. The Cl—Zn—Cl bond angle is 117.35 (6)° and the O—Zn—O angle is 101.78 (13)°. The Zn—O bond distances are 1.999 (3) Å (Zn1—O1) and 1.968 (3) Å (Zn1—O2), while the Zn—Cl bond distances are 2.2088 (14) Å (Zn1—Cl1) and 2.2147 (13) Å (Zn1—Cl2).

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

The bromide analog, complex (II), crystallizes in the monoclinic space group C2/c, with the zinc ion lying on a crystallographic twofold axis. The Zn1—Br1 bond distance is 2.3476 (7) Å, whereas the Zn1—O1 bond distance is 1.995 (4) Å. The Br1—Zn1—Br1ⁱ [symmetry code: (i) 1 − x, y, $[{1\over 2}]$ − z) bond angle is more open at 119.21 (5)° compared to the O1—Zn1—O1ⁱ bond angle of 101.6 (3)° in the pseudo-tetrahedral environment (Fig. 2).

Figure 2
The molecular structure of (II) with displacement ellipsoids drawn at the 50% probability level.

For the iodide derivative, complex (III), which crystallizes in the triclinic space group P $[\overline{1}]$ (Fig. 3), the pseudo-tetrahedral coordination environment seen in (I) is preserved. The I1—Zn1—I2 bond angle is even more open at 122.378 (14)°, with Zn1—I1 and Zn1—I2 bond distances of 2.5591 (4) Å and 2.5504 (4) Å, respectively. The O1—Zn1—O2 bond angle is compressed at 103.62 (9)°, with Zn1—O1 and Zn1—O2 bond distances of 2.0130 (19) Å and 2.016 (2) Å, respectively.

Figure 3
The molecular structure of (III) with displacement ellipsoids drawn at the 50% probability level.

Complex (IV), the perchlorate derivative, crystallizes in the trigonal space group R $[\overline{3}]$ (Fig. 4) and adopts a pseudo-octahedral arrangement around the Zn^II center, coordinated by six iQNO molecules. Two perchlorate ions reside in the lattice. The O1—Zn1—O1′ bond angles range from 85.82 (4) to 94.18 (4)°, and the associated Zn1—O1 bond distances are 2.1008 (11) Å.

Figure 4
The molecular structure of (IV) with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms removed for clarity.

Compound (V) crystallizes in the triclinic space group P $[\overline{1}]$ and exhibits a pseudo-octahedral arrangement around the Zn^II center (Fig. 5). Of the five water molecules coordinated to the zinc ion, the equatorial Zn1—O bond distances range from 2.015 (2) Å to 2.130 (2) Å, while the axial Zn1—O7 bond distance is slightly longer at 2.174 (2) Å. The iQNO ligand is coordinated via O1 [Zn1—O1 = 2.1078 (19) Å], a distance comparable to the Zn—O bonds to water.

Figure 5
The molecular structure of (V) with displacement ellipsoids drawn at the 50% probability level.

The coordinated iQNO ligands participate in π–π stacking interactions. The centroid-to-centroid distances between aromatic rings lie in the range of approximately 3.66–3.97 Å. Hydrogen bonding in compound (V) is also notable. The nitrate ion associated with N4 (bearing atoms O9, O10 and O11) accepts hydrogen bonds from water molecules O6 [O6⋯O9 = 2.723 (3) Å] and O8 [O8⋯O10 = 2.808 (3) Å]. Similarly, the nitrate ion associated with N5 (O12, O13, O14) accepts a hydrogen bond from O8 [O8⋯O12 = 2.710 (3) Å]. The iQNO ligands also participate in hydrogen bonding: O2 and O3 from the iQNO moieties accept hydrogen bonds from O6 and O4, respectively [O6⋯O2 = 2.651 (3) Å; O4⋯O3 = 2.634 (3) Å] (Table 1).

Table 1
Hydrogen-bond geometry (Å, °) for (V)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O9	0.82 (2)	1.91 (2)	2.723 (3)	173 (4)
O5—H5A⋯O13ⁱⁱ	0.83 (2)	2.04 (2)	2.861 (3)	168 (3)
O8—H8A⋯O10	0.83 (2)	2.00 (2)	2.808 (3)	164 (4)
O5—H5B⋯O9ⁱⁱⁱ	0.83 (2)	1.98 (2)	2.802 (3)	171 (4)
O6—H6B⋯O2	0.82 (2)	1.84 (2)	2.651 (3)	177 (3)
O7—H7A⋯O3ⁱⁱ	0.82 (2)	2.03 (2)	2.798 (3)	156 (3)
O8—H8B⋯O12	0.83 (2)	1.88 (2)	2.710 (3)	179 (4)
O7—H7B⋯O2ⁱⁱⁱ	0.82 (2)	1.94 (2)	2.755 (3)	173 (4)
O4—H4A⋯O3	0.82 (2)	1.81 (2)	2.634 (3)	176 (5)
O4—H4B⋯O12ⁱⁱ	0.81 (2)	1.93 (2)	2.729 (3)	169 (4)
Symmetry codes: (ii) ; (iii) .

3. Supramolecular features

Figs. 6–10 show the crystal packing of compounds (I)–(V), respectively. In the packing of (I), (II), (III), and (IV) the packing is consolidated by van der Waals interactions and π–π stacking. In the case of (V), there is an additional network of intermolecular O—H⋯O hydrogen bonds.

Figure 6
A view along the a-axis direction of the crystal packing of (I).

Figure 7
A view along the c-axis direction of the crystal packing of (II).

Figure 8
A view along the a-axis direction of the crystal packing of (III).

Figure 9
A view along the b-axis direction of the crystal packing of (IV).

Figure 10
A view along the a-axis direction of the crystal packing of (V).

In (I), several π–π contacts are observed between inversion-related rings, with centroid–centroid distances ranging from 3.835 (3) to 3.966 (3) Å (Table 2). These interactions stack the molecules into layered ribbons that extend along the b-axis direction. Compound (II) also exhibits aromatic stacking. Cg2⋯Cg2ⁱ contacts [3.634 (5) Å; symmetry code: (i) $[{1\over 2}]$ − x, $[{3\over 2}]$ − y, 1 − z] and Cg1⋯Cg1ⁱⁱ contacts [3.666 (4) Å; symmetry code: (ii) 1 − x, 2 − y, 1 − z] form columnar arrays running through the crystal. One set of columns runs along the [110] direction, and the other along the [1 $[\overline{1}]$ 0] direction. Similarly, in (III), several strong π–π interactions are observed: Cg2⋯Cg2ⁱ = 3.802 (3) Å [symmetry code: (i) 1 − x, −y, −z], Cg3⋯Cg3ⁱⁱ = 3.632 (2) Å [symmetry code: (ii) 1 − x, 1 − y, 1 − z], and Cg4⋯Cg4ⁱⁱⁱ = 3.681 (2) Å [symmetry code: (iii) 1 − x, 2 − y, 1 − z]. These interactions result in columnar arrays running along the b-axis direction, with the columns connected by additional π–π interactions to form sheets in the bc plane.

Table 2
Centroid distances (Å) for (I)

Cg–Cg4 are the centroids of the N1/C1/C2/C7–C9, N2/C10–C12/C17/C18, C2–C7 and C12–C17 rings, respectively.

Cg1⋯Cg1ⁱ	3.928 (4)	Cg3⋯Cg3ⁱⁱ	3.845 (4)
Cg1⋯Cg3ⁱ	3.966 (3)	Cg4⋯Cg4^iv	3.681 (4)
Cg1⋯Cg3ⁱⁱ	3.835 (3)	Cg4⋯Cg2ⁱⁱⁱ	3.940 (3)
Cg2⋯Cg2ⁱⁱⁱ	3.437 (3)	Cg4⋯Cg2^iv	3.906 (3)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

In contrast, (IV) exhibits fewer and weaker contacts, with Cg2⋯Cg1ⁱ at 3.9288 (13) Å [symmetry code: (i) 1 − x, 1 − y, 1 − z] being the only observed π–π stacking interaction. Compound (V) has multiple π–π contacts, with centroid–centroid distances ranging from 3.7374 (19) to 3.969 (2) Å (Table 3). In addition to aromatic stacking, (V) is also consolidated by hydrogen bonds involving coordinated water molecules and nitrate anions. Notable examples include O6—H6A⋯O9 [O⋯O = 2.723 (3) Å], O6—H6B⋯O2 [2.651 (3) Å], O5—H5A⋯O13ⁱⁱ [2.861 (3) Å], O5—H5B⋯O9ⁱⁱⁱ [2.802 (3) Å], and O8—H8B⋯O12 [2.710 (3) Å]. These hydrogen bonds, with D—H⋯A angles often approaching linearity [e.g., 177 (3)° for O6—H6B⋯O2], tie the complexes together into a robust three-dimensional network [symmetry codes: (ii) −x + 1, −y + 1, −z + 1; (iii) −x + 1, −y, –z + 1].

Table 3
Centroid distances (Å) for (V)

Cg1, Cg2, Cg4, Cg5, Cg7 and Cg8 are the centroids of the N1/C1–C3/C8/C9, C3–C8, N2/C10–C12/C17/C18, C12–C17, N3/C19–C21/C26/C27 and C21–C26 rings, respectively.

Cg1⋯Cg4	3.839 (2)	Cg2⋯Cg8	3.969 (2)
Cg1⋯Cg7	3.893 (2)	Cg4⋯Cg7ⁱ	3.943 (2)
Cg1⋯Cg8	3.8500 (19)	Cg5⋯Cg7ⁱ	3.7374 (19)
Cg2⋯Cg4	3.6617 (19)	Cg5⋯Cg8ⁱ	3.968 (2)
Cg2⋯Cg5	3.823 (2)
Symmetry code: (i) .

4. Hirshfeld surface analysis

The intermolecular interactions were further investigated by quantitative analysis of the Hirshfeld surfaces using CrystalExplorer 21 (Spackman et al., 2021 ), and visualized via two-dimensional fingerprint plots (McKinnon et al., 2007 ). Figs. 11, 12 and 13 show the Hirshfeld surfaces of molecules (I)–(III), each mapped with the function d_norm, which is the sum of the distances from a surface point to the nearest interior (d_i) and exterior (d_e) atoms, normalized by the van der Waals (vdW) radii of the corresponding atoms (r_vdW). Contacts shorter than the sums of vdW radii are shown in red, those longer in blue, and those approximately equal to vdW in white.

Figure 11
Hirshfeld surface for (I) mapped over d_norm.

Figure 12
Hirshfeld surface for (II) mapped over d_norm.

Figure 13
Hirshfeld surface for (III) mapped over d_norm.

For (I), (II), and (III), the most intense red spots correspond to C—H⋯X and C—H⋯O interactions. In (I), the short contact C10—H10⋯O2(2 − x, 1 − y, −z) has an H⋯O distance of 2.447 (3) Å. Additional short contacts include C11—H11⋯Cl2(2 − x, −y, −z) at 2.8305 (13) Å and C8—H8⋯Cl2(2 − x, 1 − y, 1 − z) at 2.8649 (13) Å. In (II), the most significant short contacts are C5—H5⋯Br1( $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z) at 2.9832 (6) Å and C4—H4⋯O1( $[{1\over 2}]$ + x, − $[{1\over 2}]$ + y, z) at 2.670 (4) Å. In (III), the short contacts C4—H4⋯O1(x, 1 + y, z) at 2.669 (2) Å and C18—H18⋯O2(2 − x, 1 − y, 1 − z) at 2.566 (2) Å are also observed. All of these short contacts can be regarded as weak hydrogen bonds (Steiner, 1998 ).

In (IV), (Fig. 14), the shortest contacts correspond to C—H⋯O interactions, primarily C4—H4⋯O3( $[{2\over 3}]$ + y − x, $[{4\over 3}]$ − x, $[{1\over 3}]$ + z) at 2.4079 (18) Å. In (V), (Fig. 15), the closest contacts are the hydrogen bonds between IQNO and the water molecules, and between the nitrate ions and water described above; there are also weak hydrogen bonds involving C1—H1⋯O2(−x, 1 − y, 1 − z) at 2.319 (2) Å and C19—H19⋯O1(−x, 1 − y, 1 − z) at 2.402 (2) Å.

Figure 14
Hirshfeld surface for (IV) mapped over d_norm.

Figure 15
Hirshfeld surface for (V) mapped over d_norm.

Analysis of the two-dimensional fingerprint plots (Table 4) indicates that H⋯H contacts are the most common in all five structures. In (I)–(III), the X⋯H contacts constitute the second-highest contribution, which increases in the order (I) < (II) < (III), contributing 29.0%, 30.9%, and 31.1%, respectively. In (IV) and (V), the Hirshfeld surface for the Zn complex was used in the analysis, and O⋯H contacts form the second-highest contribution, contributing 24.5%, 37.6%, and 31.1%, respectively. No short halogen⋯halogen contacts are observed in (I)–(III).

Table 4
Contributions of selected intermolecular contacts (%) to the Hirshfeld surfaces of (I)–(V)

Compound	(I)	(II)	(III)	(IV)	(V)
H⋯H	30.9	27.8	28.0	41.8	40.6
H⋯X/X⋯H	29.0	30.9	31.1	–	–
C⋯H/H⋯C	13.3	20.1	17.2	22.0	8.6
C⋯C	11.3	6.6	7.0	6.0	8.5
O⋯H/H⋯O	8.8	8.3	7.9	24.5	37.6

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.42, update September 2022; Groom et al., 2016 ) for isoquinoline N-oxide returned 14 unique entries. Of these 14, only 5 were bound directly to metal atoms. The most closely related to these complexes are cobalt(II) [CSD refcodes PINNUX (Munn et al., 2014 ) and QIWWEB (Kawamura et al., 2019 )], niobium(III) (QARFAU; Sperlich & Kockerling, 2022 ), zinc(II) (UWIPAS; Oberda et al., 2011 ), and osmium(VIII) (XONBIP; Calabrese et al., 2024 ).

When the seven hydrogen atoms are removed in the substructure search, the number of unique entries increases to 72, with four additional metal-bound examples not mentioned above. These include a 1-sulfanyl-isoquinoline ruthenium(II) complex (MUTSAY; Kladnik et al., 2020 ), a 1-(oxy)-3-isoquinoline-N-oxide-carboxamidato derivative with indium(III) (VOLNIU; Seitz et al., 2008 ), a sodium derivative of iQNO with amino/crown ether attachment (ZEXCAG; Suwińska, 1995 ), and a europium(II) iQNO derivative modified with a cyclic bipyridyl (ZODXIZ; Paul-Roth et al., 1995 ).

6. Synthesis and crystallization

The title compounds were all synthesized in a similar manner. The zinc salt was dissolved in ∼10 ml of methanol, and then isoquinoline N-oxide (iQNO) was added in one portion. The solutions were stirred for 5 minutes, and the solvent was allowed to evaporate, resulting in crystalline solids over time.

Compound (I) was prepared by adding ZnCl₂ (0.0463 g, 0.340 mmol, purchased from Strem Chemicals) to a small portion of methanol to dissolve, and adding 0.100 g of iQNO (0.689 mmol, purchased from Aldrich/Millipore) in a 1:2 zinc(II):iQNO mole ratio. The solution was stirred for approximately 10 minutes, at which time the solution was covered with parafilm, and the solvent was allowed to evaporate at 295 K. Yield: 0.123 g (84.1%).

Compound (II) was synthesized by placing 0.0818 g (0.340 mmol, purchased from Alfa Aesar) of ZnBr₂·0.86H₂O in a small beaker and dissolving it in minimal amounts of methanol. iQNO (0.100 g, 0.689 mmol, purchased from Aldrich/Millipore) was added in one portion. The mixture was stirred for 10 minutes, covered with parafilm, and allowed to evaporate at 295 K. Yield: 0.138 g (75.9%).

For compound (III), a similar technique was used. ZnI₂ (0.109 g, 0.340 mmol, purchased from Aldrich/Millipore) was placed in a beaker, and methanol was added to dissolve it completely. iQNO (0.100 g, 0.689 mmol, purchased from Aldrich/Millipore) was added in one portion. The mixture was stirred for 10 minutes, covered with parafilm, and allowed to evaporate at 295 K. Yield: 0.146 g (69.8%).

Complex (IV) was prepared in a 1:4 zinc(II):iQNO ratio by dissolving 0.0633 g (0.0170 mmol, purchased from Aldrich/Millipore) of Zn(ClO₄)₂·6H₂O in methanol and adding 0.100 g (0.689 mmol) of iQNO in one portion. The solution was stirred for 10 minutes, and the solvent was evaporated to a minimum amount of liquid. This liquid was redissolved in tetrahydrofuran, dried over MgSO₄, and the solvent was evaporated. The resulting solid was dissolved in acetonitrile, which was allowed to evaporate at room temperature, yielding the product. Yield: 0.0423 g (32.4% based on iQNO).

Compound (V) was synthesized by dissolving 0.0994 g (0.340 mmol, purchased from Alfa Aesar) of Zn(NO₃)₂^.6H₂O in methanol and adding 0.100 g of iQNO (0.689 mmol) in a 1:2 ratio. The same procedure as outlined for (IV) was followed, with a final yield of 0.0642 g (39.1% based on iQNO).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. All carbon-bound H atoms were positioned geometrically and refined as riding: C—H = 0.95–0.98 Å with U_iso(H) = 1.2U_eq(C).

Table 5
Experimental details

	(I)	(II)	(III)	(IV)	(V)
Crystal data
Chemical formula	[ZnCl₂(C₉H₇NO)₂]	[ZnBr₂(C₉H₇NO)₂]	[ZnI₂(C₉H₇NO)₂]	[Zn(C₉H₇NO)₆](ClO₄)₂	[Zn(C₉H₇NO)(H₂O)₅](NO₃)₂·2C₉H₇NO
M_r	426.58	515.50	609.48	1135.20	714.94
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, C2/c	Triclinic, P $[\overline{1}]$	Trigonal, R $[\overline{3}]$	Triclinic, P $[\overline{1}]$
Temperature (K)	293	170	170	170	170
a, b, c (Å)	7.5164 (5), 7.8002 (5), 15.1156 (10)	17.1095 (10), 7.2020 (6), 14.9534 (11)	7.7325 (3), 8.9596 (4), 14.8297 (9)	12.8217 (4), 12.8217 (4), 26.5684 (9)	9.7360 (9), 11.5910 (9), 14.6381 (10)
α, β, γ (°)	96.172 (6), 92.052 (5), 96.284 (5)	90, 96.472 (6), 90	93.205 (4), 99.873 (4), 104.852 (4)	90, 90, 120	74.352 (6), 74.620 (7), 81.633 (7)
V (Å³)	874.77 (10)	1830.9 (2)	972.98 (9)	3782.6 (3)	1528.8 (2)
Z	2	4	2	3	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	1.72	5.72	4.45	0.67	0.88
Crystal size (mm)	0.4 × 0.3 × 0.1	0.2 × 0.2 × 0.2	0.32 × 0.13 × 0.06	0.2 × 0.2 × 0.15	0.7 × 0.2 × 0.04

Data collection
Diffractometer	XtaLAB Synergy, HyPix3000	XtaLAB Mini	XtaLAB Mini	XtaLAB Mini	XtaLAB Mini
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.929, 1.000	0.358, 1.000	0.535, 1.000	0.914, 1.000	0.752, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4838, 3207, 2357	2980, 1671, 1402	8495, 3563, 3152	11238, 1545, 1450	13628, 5599, 4252
R_int	0.029	0.044	0.016	0.017	0.047
(sin θ/λ)_max (Å⁻¹)	0.602	0.602	0.602	0.602	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 1.06	0.052, 0.141, 1.03	0.020, 0.048, 1.03	0.028, 0.077, 1.06	0.044, 0.106, 1.04
No. of reflections	3207	1671	3563	1545	5599
No. of parameters	226	114	226	117	464
No. of restraints	0	0	0	0	10
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.30	0.83, −0.96	0.59, −0.39	0.30, −0.25	0.51, −0.48
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 2415566; 2415565; 2415564; 2415563; 2415562

Crystal structure: contains datablocks I, II, III, IV, V. DOI: https://doi.org/10.1107/S2056989025000180/hb8119sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025000180/hb8119Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989025000180/hb8119IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989025000180/hb8119IIIsup4.hkl

Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989025000180/hb8119IVsup5.hkl

Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2056989025000180/hb8119Vsup6.hkl

checkCIF report

Computing details top

Dichloridobis(isoquinoline N-oxide-κO)zinc(II) (I) top

Crystal data top

[ZnCl₂(C₉H₇NO)₂]	Z = 2
M_r = 426.58	F(000) = 432
Triclinic, P1	D_x = 1.620 Mg m⁻³
a = 7.5164 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8002 (5) Å	Cell parameters from 520 reflections
c = 15.1156 (10) Å	θ = 2.7–22.6°
α = 96.172 (6)°	µ = 1.72 mm⁻¹
β = 92.052 (5)°	T = 293 K
γ = 96.284 (5)°	Irregular, clear colourless
V = 874.77 (10) Å³	0.4 × 0.3 × 0.1 mm

Data collection top

XtaLAB Synergy, HyPix3000 diffractometer	3207 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source	2357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 25.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −9→9
T_min = 0.929, T_max = 1.000	k = −9→8
4838 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0519P)² + 0.0439P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3207 reflections	Δρ_max = 0.55 e Å⁻³
226 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.94135 (7)	0.67381 (7)	0.23426 (3)	0.0471 (2)
Cl2	1.10215 (18)	0.47387 (17)	0.27790 (8)	0.0642 (4)
Cl1	1.0537 (2)	0.94814 (17)	0.26629 (9)	0.0698 (4)
O2	0.8996 (4)	0.6204 (4)	0.10445 (19)	0.0526 (8)
O1	0.6934 (4)	0.6319 (5)	0.27690 (19)	0.0628 (9)
N2	0.7659 (5)	0.6628 (4)	0.0538 (2)	0.0433 (9)
N1	0.6497 (5)	0.6711 (5)	0.3619 (2)	0.0465 (9)
C1	0.4937 (6)	0.7275 (6)	0.3769 (3)	0.0474 (11)
H1	0.417826	0.742590	0.329117	0.057*
C16	0.3419 (7)	0.8481 (6)	0.0684 (3)	0.0558 (12)
H16	0.340539	0.880666	0.129381	0.067*
C10	0.7735 (6)	0.6177 (6)	−0.0366 (3)	0.0473 (11)
H10	0.870860	0.566543	−0.059286	0.057*
C2	0.4403 (6)	0.7651 (5)	0.4644 (3)	0.0444 (10)
C7	0.5573 (6)	0.7419 (5)	0.5355 (3)	0.0450 (11)
C11	0.6378 (7)	0.6485 (6)	−0.0920 (3)	0.0543 (12)
H11	0.643301	0.618191	−0.152943	0.065*
C18	0.6327 (6)	0.7382 (6)	0.0875 (3)	0.0464 (11)
H18	0.633820	0.769454	0.148655	0.056*
C6	0.5010 (8)	0.7816 (7)	0.6236 (3)	0.0622 (14)
H6	0.575863	0.767927	0.672033	0.075*
C8	0.7216 (6)	0.6805 (6)	0.5152 (3)	0.0528 (12)
H8	0.801520	0.663881	0.561100	0.063*
C3	0.2723 (6)	0.8255 (6)	0.4807 (3)	0.0541 (12)
H3	0.195615	0.841291	0.433315	0.065*
C17	0.4855 (6)	0.7738 (5)	0.0328 (3)	0.0445 (11)
C9	0.7644 (6)	0.6456 (6)	0.4302 (3)	0.0544 (12)
H9	0.873034	0.603814	0.417646	0.065*
C14	0.2034 (7)	0.8278 (7)	−0.0791 (4)	0.0684 (15)
H14	0.108847	0.849968	−0.115940	0.082*
C12	0.4906 (6)	0.7244 (5)	−0.0598 (3)	0.0467 (11)
C15	0.2012 (7)	0.8732 (7)	0.0129 (4)	0.0640 (14)
H15	0.102906	0.921058	0.036766	0.077*
C5	0.3395 (8)	0.8389 (7)	0.6375 (3)	0.0678 (15)
H5	0.304849	0.864656	0.695408	0.081*
C4	0.2242 (7)	0.8599 (7)	0.5655 (3)	0.0626 (14)
H4	0.113135	0.898061	0.576242	0.075*
C13	0.3403 (7)	0.7526 (7)	−0.1148 (3)	0.0615 (13)
H13	0.337385	0.718600	−0.175771	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0432 (3)	0.0575 (4)	0.0421 (3)	0.0109 (2)	0.0037 (2)	0.0062 (2)
Cl2	0.0699 (9)	0.0717 (8)	0.0564 (7)	0.0294 (7)	−0.0025 (6)	0.0127 (6)
Cl1	0.0879 (11)	0.0572 (8)	0.0628 (8)	0.0093 (7)	0.0064 (7)	−0.0027 (6)
O2	0.045 (2)	0.070 (2)	0.0453 (17)	0.0194 (16)	−0.0029 (15)	0.0053 (15)
O1	0.049 (2)	0.101 (3)	0.0377 (17)	0.0051 (18)	0.0113 (15)	0.0018 (17)
N2	0.040 (2)	0.046 (2)	0.044 (2)	0.0067 (17)	0.0032 (17)	0.0074 (17)
N1	0.037 (2)	0.064 (2)	0.039 (2)	0.0006 (17)	0.0053 (17)	0.0110 (18)
C1	0.039 (3)	0.058 (3)	0.045 (2)	0.001 (2)	−0.002 (2)	0.012 (2)
C16	0.051 (3)	0.058 (3)	0.063 (3)	0.011 (2)	0.013 (3)	0.016 (2)
C10	0.051 (3)	0.051 (3)	0.040 (2)	0.009 (2)	0.004 (2)	0.005 (2)
C2	0.040 (3)	0.047 (3)	0.046 (2)	0.003 (2)	0.003 (2)	0.007 (2)
C7	0.046 (3)	0.048 (3)	0.042 (2)	0.001 (2)	0.002 (2)	0.013 (2)
C11	0.062 (3)	0.060 (3)	0.041 (2)	0.008 (2)	0.005 (2)	0.002 (2)
C18	0.051 (3)	0.049 (3)	0.041 (2)	0.008 (2)	0.002 (2)	0.008 (2)
C6	0.074 (4)	0.075 (4)	0.039 (3)	0.011 (3)	0.003 (3)	0.013 (2)
C8	0.043 (3)	0.070 (3)	0.048 (3)	0.007 (2)	−0.004 (2)	0.019 (2)
C3	0.044 (3)	0.065 (3)	0.054 (3)	0.008 (2)	0.002 (2)	0.006 (2)
C17	0.043 (3)	0.045 (3)	0.047 (3)	0.001 (2)	0.008 (2)	0.011 (2)
C9	0.042 (3)	0.073 (3)	0.051 (3)	0.012 (2)	0.006 (2)	0.014 (2)
C14	0.052 (3)	0.069 (4)	0.088 (4)	0.006 (3)	−0.011 (3)	0.030 (3)
C12	0.047 (3)	0.037 (2)	0.056 (3)	0.0006 (19)	0.003 (2)	0.009 (2)
C15	0.042 (3)	0.066 (3)	0.090 (4)	0.012 (2)	0.006 (3)	0.031 (3)
C5	0.080 (4)	0.076 (4)	0.050 (3)	0.013 (3)	0.022 (3)	0.009 (3)
C4	0.058 (3)	0.068 (3)	0.062 (3)	0.013 (3)	0.012 (3)	0.002 (3)
C13	0.064 (4)	0.063 (3)	0.056 (3)	0.003 (3)	−0.011 (3)	0.014 (2)

Geometric parameters (Å, º) top

Zn1—Cl2	2.2147 (13)	C11—H11	0.9300
Zn1—Cl1	2.2088 (14)	C11—C12	1.390 (6)
Zn1—O2	1.968 (3)	C18—H18	0.9300
Zn1—O1	1.999 (3)	C18—C17	1.426 (6)
O2—N2	1.332 (4)	C6—H6	0.9300
O1—N1	1.349 (4)	C6—C5	1.354 (7)
N2—C10	1.378 (5)	C8—H8	0.9300
N2—C18	1.308 (5)	C8—C9	1.343 (6)
N1—C1	1.316 (5)	C3—H3	0.9300
N1—C9	1.366 (6)	C3—C4	1.353 (6)
C1—H1	0.9300	C17—C12	1.414 (6)
C1—C2	1.405 (6)	C9—H9	0.9300
C16—H16	0.9300	C14—H14	0.9300
C16—C17	1.379 (6)	C14—C15	1.400 (7)
C16—C15	1.370 (7)	C14—C13	1.340 (7)
C10—H10	0.9300	C12—C13	1.429 (7)
C10—C11	1.355 (6)	C15—H15	0.9300
C2—C7	1.404 (6)	C5—H5	0.9300
C2—C3	1.416 (6)	C5—C4	1.401 (7)
C7—C6	1.424 (6)	C4—H4	0.9300
C7—C8	1.405 (6)	C13—H13	0.9300

Cg1···Cg1ⁱ	3.928 (4)	Cg3···Cg3ⁱⁱ	3.845 (4)
Cg1···Cg3ⁱ	3.966 (3)	Cg4···Cg4^iv	3.681 (4)
Cg1···Cg3ⁱⁱ	3.835 (3)	Cg4···Cg2ⁱⁱⁱ	3.940 (3)
Cg2···Cg2ⁱⁱⁱ	3.437 (3)	Cg4···Cg2^iv	3.906 (3)

Cl1—Zn1—Cl2	117.35 (6)	C17—C18—H18	119.1
O2—Zn1—Cl2	106.39 (9)	C7—C6—H6	119.7
O2—Zn1—Cl1	109.57 (10)	C5—C6—C7	120.7 (5)
O2—Zn1—O1	101.78 (13)	C5—C6—H6	119.7
O1—Zn1—Cl2	109.07 (12)	C7—C8—H8	119.7
O1—Zn1—Cl1	111.43 (11)	C9—C8—C7	120.6 (4)
N2—O2—Zn1	127.6 (2)	C9—C8—H8	119.7
N1—O1—Zn1	124.0 (3)	C2—C3—H3	120.2
O2—N2—C10	115.9 (3)	C4—C3—C2	119.6 (5)
C18—N2—O2	122.4 (4)	C4—C3—H3	120.2
C18—N2—C10	121.6 (4)	C16—C17—C18	121.8 (4)
O1—N1—C9	119.7 (4)	C16—C17—C12	121.2 (4)
C1—N1—O1	118.8 (4)	C12—C17—C18	116.9 (4)
C1—N1—C9	121.5 (4)	N1—C9—H9	119.7
N1—C1—H1	119.6	C8—C9—N1	120.5 (4)
N1—C1—C2	120.8 (4)	C8—C9—H9	119.7
C2—C1—H1	119.6	C15—C14—H14	119.6
C17—C16—H16	120.4	C13—C14—H14	119.6
C15—C16—H16	120.4	C13—C14—C15	120.8 (5)
C15—C16—C17	119.3 (5)	C11—C12—C17	118.8 (4)
N2—C10—H10	120.3	C11—C12—C13	123.8 (4)
C11—C10—N2	119.4 (4)	C17—C12—C13	117.4 (4)
C11—C10—H10	120.3	C16—C15—C14	120.8 (5)
C1—C2—C3	120.8 (4)	C16—C15—H15	119.6
C7—C2—C1	118.6 (4)	C14—C15—H15	119.6
C7—C2—C3	120.5 (4)	C6—C5—H5	119.6
C2—C7—C6	117.7 (4)	C6—C5—C4	120.7 (5)
C2—C7—C8	117.9 (4)	C4—C5—H5	119.6
C8—C7—C6	124.3 (4)	C3—C4—C5	120.8 (5)
C10—C11—H11	119.2	C3—C4—H4	119.6
C10—C11—C12	121.5 (4)	C5—C4—H4	119.6
C12—C11—H11	119.2	C14—C13—C12	120.4 (5)
N2—C18—H18	119.1	C14—C13—H13	119.8
N2—C18—C17	121.7 (4)	C12—C13—H13	119.8

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

Dibromidobis(isoquinoline N-oxide-κO)zinc(II) (II) top

Crystal data top

[ZnBr₂(C₉H₇NO)₂]	F(000) = 1008
M_r = 515.50	D_x = 1.870 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.1095 (10) Å	Cell parameters from 2412 reflections
b = 7.2020 (6) Å	θ = 2.5–33.1°
c = 14.9534 (11) Å	µ = 5.72 mm⁻¹
β = 96.472 (6)°	T = 170 K
V = 1830.9 (2) Å³	Block, clear colourless
Z = 4	0.2 × 0.2 × 0.2 mm

Data collection top

XtaLAB Mini diffractometer	1671 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1402 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −16→20
T_min = 0.358, T_max = 1.000	k = −8→8
2980 measured reflections	l = −18→17

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0927P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1671 reflections	Δρ_max = 0.83 e Å⁻³
114 parameters	Δρ_min = −0.96 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.60954 (3)	0.37505 (9)	0.21097 (4)	0.0370 (3)
Zn1	0.500000	0.53998 (12)	0.250000	0.0276 (3)
O1	0.5369 (2)	0.7150 (6)	0.3493 (3)	0.0362 (9)
N1	0.4810 (2)	0.7741 (6)	0.3999 (3)	0.0293 (10)
C2	0.3560 (3)	0.9088 (7)	0.4148 (4)	0.0274 (12)
C7	0.3704 (3)	0.8846 (7)	0.5089 (4)	0.0306 (13)
C1	0.4157 (3)	0.8517 (7)	0.3621 (4)	0.0293 (12)
H1	0.408573	0.869682	0.298816	0.035*
C3	0.2848 (3)	0.9829 (8)	0.3750 (5)	0.0357 (13)
H3	0.275439	0.998479	0.311593	0.043*
C9	0.4960 (3)	0.7503 (8)	0.4919 (4)	0.0342 (13)
H9	0.544037	0.695474	0.517045	0.041*
C4	0.2289 (3)	1.0325 (8)	0.4292 (5)	0.0393 (15)
H4	0.180142	1.081746	0.403055	0.047*
C8	0.4426 (3)	0.8049 (7)	0.5454 (4)	0.0325 (12)
H8	0.453412	0.790004	0.608739	0.039*
C6	0.3108 (4)	0.9413 (8)	0.5627 (5)	0.0383 (14)
H6	0.319011	0.929530	0.626322	0.046*
C5	0.2426 (4)	1.0119 (8)	0.5222 (5)	0.0443 (17)
H5	0.202956	1.048433	0.558206	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0276 (4)	0.0536 (4)	0.0301 (4)	0.0097 (2)	0.0041 (2)	−0.0043 (3)
Zn1	0.0200 (5)	0.0393 (5)	0.0237 (5)	0.000	0.0032 (3)	0.000
O1	0.0189 (18)	0.053 (2)	0.037 (2)	0.0036 (17)	0.0060 (15)	−0.013 (2)
N1	0.021 (2)	0.037 (2)	0.030 (3)	−0.0015 (18)	0.0032 (17)	−0.008 (2)
C2	0.023 (3)	0.031 (3)	0.028 (3)	−0.002 (2)	0.000 (2)	0.003 (2)
C7	0.026 (3)	0.035 (3)	0.031 (3)	−0.006 (2)	0.004 (2)	−0.004 (2)
C1	0.025 (3)	0.038 (3)	0.024 (3)	−0.004 (2)	−0.001 (2)	0.000 (2)
C3	0.026 (3)	0.038 (3)	0.042 (4)	−0.004 (2)	0.003 (2)	0.002 (3)
C9	0.027 (3)	0.042 (3)	0.032 (3)	−0.003 (2)	−0.004 (2)	0.003 (3)
C4	0.023 (3)	0.039 (3)	0.056 (4)	0.000 (2)	0.003 (3)	0.002 (3)
C8	0.038 (3)	0.033 (3)	0.024 (3)	−0.001 (2)	−0.005 (2)	0.004 (3)
C6	0.042 (4)	0.037 (3)	0.039 (4)	−0.007 (3)	0.015 (3)	−0.008 (3)
C5	0.028 (3)	0.043 (3)	0.065 (5)	−0.002 (2)	0.022 (3)	−0.011 (3)

Geometric parameters (Å, º) top

Zn1—Br1	2.3476 (7)	C1—H1	0.9500
Zn1—Br1ⁱ	2.3476 (7)	C3—H3	0.9500
Zn1—O1	1.995 (4)	C3—C4	1.369 (8)
Zn1—O1ⁱ	1.995 (4)	C9—H9	0.9500
O1—N1	1.353 (5)	C9—C8	1.340 (8)
N1—C1	1.317 (7)	C4—H4	0.9500
N1—C9	1.381 (8)	C4—C5	1.391 (10)
C2—C7	1.411 (8)	C8—H8	0.9500
C2—C1	1.421 (8)	C6—H6	0.9500
C2—C3	1.400 (8)	C6—C5	1.351 (9)
C7—C8	1.416 (8)	C5—H5	0.9500
C7—C6	1.428 (8)

Br1—Zn1—Br1ⁱ	119.21 (5)	C2—C3—H3	120.7
O1—Zn1—Br1	108.06 (10)	C4—C3—C2	118.6 (6)
O1ⁱ—Zn1—Br1ⁱ	108.06 (10)	C4—C3—H3	120.7
O1—Zn1—Br1ⁱ	109.22 (11)	N1—C9—H9	120.1
O1ⁱ—Zn1—Br1	109.22 (11)	C8—C9—N1	119.7 (5)
O1—Zn1—O1ⁱ	101.6 (3)	C8—C9—H9	120.1
N1—O1—Zn1	115.5 (3)	C3—C4—H4	119.5
O1—N1—C9	117.0 (4)	C3—C4—C5	120.9 (6)
C1—N1—O1	120.8 (5)	C5—C4—H4	119.5
C1—N1—C9	122.2 (5)	C7—C8—H8	119.6
C7—C2—C1	117.4 (5)	C9—C8—C7	120.8 (6)
C3—C2—C7	121.2 (5)	C9—C8—H8	119.6
C3—C2—C1	121.4 (5)	C7—C6—H6	120.3
C2—C7—C8	118.8 (5)	C5—C6—C7	119.3 (6)
C2—C7—C6	118.1 (5)	C5—C6—H6	120.3
C8—C7—C6	123.1 (6)	C4—C5—H5	119.1
N1—C1—C2	120.9 (5)	C6—C5—C4	121.8 (6)
N1—C1—H1	119.5	C6—C5—H5	119.1
C2—C1—H1	119.5

Zn1—O1—N1—C1	−54.2 (6)	C1—N1—C9—C8	0.9 (8)
Zn1—O1—N1—C9	126.2 (4)	C1—C2—C7—C8	−0.2 (7)
O1—N1—C1—C2	178.1 (4)	C1—C2—C7—C6	−180.0 (5)
O1—N1—C9—C8	−179.5 (5)	C1—C2—C3—C4	178.9 (5)
N1—C9—C8—C7	0.9 (8)	C3—C2—C7—C8	178.5 (5)
C2—C7—C8—C9	−1.2 (8)	C3—C2—C7—C6	−1.2 (8)
C2—C7—C6—C5	1.4 (8)	C3—C2—C1—N1	−176.8 (5)
C2—C3—C4—C5	0.7 (9)	C3—C4—C5—C6	−0.5 (10)
C7—C2—C1—N1	2.0 (8)	C9—N1—C1—C2	−2.4 (8)
C7—C2—C3—C4	0.2 (8)	C8—C7—C6—C5	−178.4 (6)
C7—C6—C5—C4	−0.6 (9)	C6—C7—C8—C9	178.6 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

Diiodidobis(isoquinoline N-oxide-κO)zinc(II) (III) top

Crystal data top

[ZnI₂(C₉H₇NO)₂]	Z = 2
M_r = 609.48	F(000) = 576
Triclinic, P1	D_x = 2.080 Mg m⁻³
a = 7.7325 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9596 (4) Å	Cell parameters from 6528 reflections
c = 14.8297 (9) Å	θ = 2.3–33.2°
α = 93.205 (4)°	µ = 4.45 mm⁻¹
β = 99.873 (4)°	T = 170 K
γ = 104.852 (4)°	Irregular, clear colourless
V = 972.98 (9) Å³	0.32 × 0.13 × 0.06 mm

Data collection top

XtaLAB Mini diffractometer	3563 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3152 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 25.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −9→9
T_min = 0.535, T_max = 1.000	k = −10→10
8495 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.020	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0249P)² + 0.3875P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3563 reflections	Δρ_max = 0.59 e Å⁻³
226 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I2	1.04627 (3)	0.42553 (2)	0.19043 (2)	0.03413 (7)
I1	0.93556 (3)	0.87866 (2)	0.26504 (2)	0.03405 (7)
Zn1	0.84695 (4)	0.58158 (4)	0.24874 (2)	0.02607 (9)
O1	0.5914 (3)	0.5206 (2)	0.17439 (15)	0.0331 (5)
O2	0.8155 (3)	0.5066 (2)	0.37215 (14)	0.0324 (5)
N1	0.5043 (3)	0.3742 (3)	0.13534 (16)	0.0242 (5)
N2	0.7414 (3)	0.5881 (3)	0.42719 (16)	0.0261 (5)
C2	0.4420 (3)	0.0990 (3)	0.12990 (19)	0.0242 (6)
C1	0.5366 (4)	0.2500 (3)	0.17229 (19)	0.0252 (6)
H1	0.623861	0.262763	0.227653	0.030*
C7	0.3108 (4)	0.0815 (3)	0.04758 (19)	0.0251 (6)
C9	0.3765 (4)	0.3613 (3)	0.05564 (19)	0.0269 (6)
H9	0.354796	0.452253	0.031520	0.032*
C11	0.5072 (4)	0.7042 (3)	0.45488 (19)	0.0240 (6)
C16	0.6055 (4)	0.7592 (3)	0.54600 (19)	0.0251 (6)
C8	0.2815 (4)	0.2191 (3)	0.01155 (19)	0.0280 (6)
H8	0.195178	0.211549	−0.043598	0.034*
C18	0.8379 (4)	0.6377 (3)	0.5163 (2)	0.0276 (6)
H18	0.949142	0.612186	0.536568	0.033*
C17	0.7732 (4)	0.7228 (3)	0.5744 (2)	0.0280 (6)
H17	0.841205	0.758417	0.634815	0.034*
C15	0.5324 (4)	0.8477 (3)	0.6039 (2)	0.0296 (6)
H15	0.597063	0.886817	0.664503	0.036*
C3	0.4758 (4)	−0.0347 (3)	0.1682 (2)	0.0303 (6)
H3	0.564660	−0.023736	0.222759	0.036*
C12	0.3390 (4)	0.7373 (3)	0.4237 (2)	0.0303 (7)
H12	0.273178	0.700892	0.362968	0.036*
C6	0.2151 (4)	−0.0703 (3)	0.0054 (2)	0.0325 (7)
H6	0.127647	−0.084025	−0.049963	0.039*
C10	0.5825 (4)	0.6174 (3)	0.3969 (2)	0.0277 (6)
H10	0.518886	0.579961	0.335836	0.033*
C14	0.3678 (4)	0.8771 (3)	0.5723 (2)	0.0327 (7)
H14	0.318301	0.935043	0.611757	0.039*
C5	0.2493 (4)	−0.1964 (4)	0.0450 (2)	0.0353 (7)
H5	0.183619	−0.297723	0.017024	0.042*
C4	0.3804 (4)	−0.1793 (3)	0.1265 (2)	0.0345 (7)
H4	0.402405	−0.268730	0.152616	0.041*
C13	0.2717 (4)	0.8220 (3)	0.4818 (2)	0.0322 (7)
H13	0.158657	0.844158	0.460923	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I2	0.03348 (11)	0.03541 (12)	0.03325 (12)	0.00911 (9)	0.00922 (9)	−0.00629 (8)
I1	0.03325 (11)	0.02439 (11)	0.03826 (12)	0.00528 (8)	−0.00469 (9)	−0.00142 (8)
Zn1	0.02493 (17)	0.02467 (17)	0.02604 (18)	0.00437 (13)	0.00288 (14)	−0.00172 (13)
O1	0.0277 (10)	0.0225 (10)	0.0411 (13)	0.0019 (8)	−0.0047 (9)	−0.0058 (9)
O2	0.0413 (12)	0.0327 (11)	0.0313 (11)	0.0188 (9)	0.0145 (10)	0.0053 (9)
N1	0.0209 (11)	0.0216 (12)	0.0275 (13)	0.0023 (9)	0.0039 (10)	−0.0003 (10)
N2	0.0294 (13)	0.0226 (12)	0.0280 (13)	0.0066 (10)	0.0096 (11)	0.0057 (10)
C2	0.0200 (13)	0.0278 (15)	0.0253 (15)	0.0062 (11)	0.0068 (11)	0.0003 (12)
C1	0.0215 (13)	0.0285 (15)	0.0231 (14)	0.0045 (11)	0.0013 (12)	0.0026 (12)
C7	0.0227 (13)	0.0289 (15)	0.0223 (14)	0.0047 (11)	0.0050 (12)	−0.0023 (11)
C9	0.0246 (14)	0.0315 (16)	0.0254 (15)	0.0085 (12)	0.0045 (12)	0.0067 (12)
C11	0.0243 (14)	0.0213 (14)	0.0244 (15)	0.0024 (11)	0.0044 (12)	0.0038 (11)
C16	0.0230 (14)	0.0213 (14)	0.0287 (15)	0.0006 (11)	0.0063 (12)	0.0046 (11)
C8	0.0240 (14)	0.0362 (17)	0.0208 (14)	0.0053 (12)	0.0010 (12)	0.0020 (12)
C18	0.0243 (14)	0.0282 (15)	0.0296 (16)	0.0056 (12)	0.0040 (12)	0.0068 (12)
C17	0.0257 (14)	0.0281 (16)	0.0241 (15)	0.0007 (12)	−0.0020 (12)	0.0018 (12)
C15	0.0324 (16)	0.0294 (16)	0.0242 (15)	0.0018 (12)	0.0084 (13)	0.0016 (12)
C3	0.0298 (15)	0.0335 (17)	0.0282 (16)	0.0098 (13)	0.0045 (13)	0.0041 (13)
C12	0.0261 (15)	0.0293 (16)	0.0303 (16)	0.0023 (12)	−0.0006 (13)	0.0028 (12)
C6	0.0303 (16)	0.0330 (17)	0.0294 (16)	0.0031 (13)	0.0035 (13)	−0.0050 (13)
C10	0.0279 (15)	0.0270 (15)	0.0262 (15)	0.0050 (12)	0.0030 (12)	0.0040 (12)
C14	0.0330 (16)	0.0327 (17)	0.0355 (17)	0.0084 (13)	0.0155 (14)	0.0033 (13)
C5	0.0357 (17)	0.0278 (16)	0.0368 (18)	0.0015 (13)	0.0055 (14)	−0.0061 (13)
C4	0.0390 (17)	0.0294 (17)	0.0379 (18)	0.0112 (13)	0.0114 (15)	0.0055 (13)
C13	0.0241 (15)	0.0352 (17)	0.0383 (18)	0.0075 (13)	0.0081 (13)	0.0087 (13)

Geometric parameters (Å, º) top

I2—Zn1	2.5504 (4)	C16—C17	1.418 (4)
I1—Zn1	2.5591 (4)	C16—C15	1.416 (4)
Zn1—O1	2.0130 (19)	C8—H8	0.9500
Zn1—O2	2.016 (2)	C18—H18	0.9500
O1—N1	1.356 (3)	C18—C17	1.358 (4)
O2—N2	1.355 (3)	C17—H17	0.9500
N1—C1	1.328 (3)	C15—H15	0.9500
N1—C9	1.383 (4)	C15—C14	1.374 (4)
N2—C18	1.388 (4)	C3—H3	0.9500
N2—C10	1.331 (4)	C3—C4	1.367 (4)
C2—C1	1.415 (4)	C12—H12	0.9500
C2—C7	1.420 (4)	C12—C13	1.368 (4)
C2—C3	1.418 (4)	C6—H6	0.9500
C1—H1	0.9500	C6—C5	1.366 (4)
C7—C8	1.426 (4)	C10—H10	0.9500
C7—C6	1.421 (4)	C14—H14	0.9500
C9—H9	0.9500	C14—C13	1.412 (4)
C9—C8	1.361 (4)	C5—H5	0.9500
C11—C16	1.424 (4)	C5—C4	1.412 (4)
C11—C12	1.414 (4)	C4—H4	0.9500
C11—C10	1.418 (4)	C13—H13	0.9500

I2—Zn1—I1	122.378 (14)	C9—C8—H8	119.8
O1—Zn1—I2	112.15 (6)	N2—C18—H18	120.0
O1—Zn1—I1	104.01 (6)	C17—C18—N2	119.9 (3)
O1—Zn1—O2	103.62 (9)	C17—C18—H18	120.0
O2—Zn1—I2	104.06 (6)	C16—C17—H17	119.6
O2—Zn1—I1	109.19 (6)	C18—C17—C16	120.9 (3)
N1—O1—Zn1	123.46 (16)	C18—C17—H17	119.6
N2—O2—Zn1	117.46 (15)	C16—C15—H15	120.0
O1—N1—C9	116.1 (2)	C14—C15—C16	120.0 (3)
C1—N1—O1	122.2 (2)	C14—C15—H15	120.0
C1—N1—C9	121.7 (2)	C2—C3—H3	120.0
O2—N2—C18	117.0 (2)	C4—C3—C2	120.0 (3)
C10—N2—O2	121.1 (2)	C4—C3—H3	120.0
C10—N2—C18	121.9 (2)	C11—C12—H12	120.2
C1—C2—C7	119.2 (3)	C13—C12—C11	119.5 (3)
C1—C2—C3	121.2 (3)	C13—C12—H12	120.2
C3—C2—C7	119.6 (3)	C7—C6—H6	120.2
N1—C1—C2	120.5 (3)	C5—C6—C7	119.7 (3)
N1—C1—H1	119.7	C5—C6—H6	120.2
C2—C1—H1	119.7	N2—C10—C11	120.6 (3)
C2—C7—C8	117.7 (2)	N2—C10—H10	119.7
C2—C7—C6	119.1 (3)	C11—C10—H10	119.7
C6—C7—C8	123.2 (3)	C15—C14—H14	119.7
N1—C9—H9	119.8	C15—C14—C13	120.6 (3)
C8—C9—N1	120.5 (3)	C13—C14—H14	119.7
C8—C9—H9	119.8	C6—C5—H5	119.3
C12—C11—C16	120.0 (3)	C6—C5—C4	121.3 (3)
C12—C11—C10	121.4 (3)	C4—C5—H5	119.3
C10—C11—C16	118.6 (3)	C3—C4—C5	120.3 (3)
C17—C16—C11	118.1 (3)	C3—C4—H4	119.8
C15—C16—C11	118.9 (3)	C5—C4—H4	119.8
C15—C16—C17	123.1 (3)	C12—C13—C14	121.0 (3)
C7—C8—H8	119.8	C12—C13—H13	119.5
C9—C8—C7	120.4 (3)	C14—C13—H13	119.5

Zn1—O1—N1—C1	30.8 (3)	C11—C16—C15—C14	1.0 (4)
Zn1—O1—N1—C9	−150.61 (19)	C11—C12—C13—C14	0.1 (4)
Zn1—O2—N2—C18	−127.1 (2)	C16—C11—C12—C13	−0.1 (4)
Zn1—O2—N2—C10	53.5 (3)	C16—C11—C10—N2	0.1 (4)
O1—N1—C1—C2	179.5 (2)	C16—C15—C14—C13	−1.1 (4)
O1—N1—C9—C8	−179.8 (2)	C8—C7—C6—C5	−179.1 (3)
O2—N2—C18—C17	178.6 (2)	C18—N2—C10—C11	1.2 (4)
O2—N2—C10—C11	−179.4 (2)	C17—C16—C15—C14	−179.2 (3)
N1—C9—C8—C7	0.8 (4)	C15—C16—C17—C18	−179.9 (3)
N2—C18—C17—C16	1.4 (4)	C15—C14—C13—C12	0.5 (4)
C2—C7—C8—C9	−0.3 (4)	C3—C2—C1—N1	179.6 (2)
C2—C7—C6—C5	0.6 (4)	C3—C2—C7—C8	−179.9 (2)
C2—C3—C4—C5	0.6 (4)	C3—C2—C7—C6	0.3 (4)
C1—N1—C9—C8	−1.2 (4)	C12—C11—C16—C17	179.8 (2)
C1—C2—C7—C8	0.2 (4)	C12—C11—C16—C15	−0.4 (4)
C1—C2—C7—C6	−179.6 (2)	C12—C11—C10—N2	179.7 (2)
C1—C2—C3—C4	179.0 (3)	C6—C7—C8—C9	179.4 (3)
C7—C2—C1—N1	−0.5 (4)	C6—C5—C4—C3	0.4 (5)
C7—C2—C3—C4	−0.9 (4)	C10—N2—C18—C17	−2.0 (4)
C7—C6—C5—C4	−0.9 (5)	C10—C11—C16—C17	−0.7 (4)
C9—N1—C1—C2	1.0 (4)	C10—C11—C16—C15	179.1 (2)
C11—C16—C17—C18	−0.1 (4)	C10—C11—C12—C13	−179.7 (3)

Hexakis(isoquinoline N-oxide-κO)zinc(II) bis(perchlorate) (IV) top

Crystal data top

[Zn(C₉H₇NO)₆](ClO₄)₂	D_x = 1.495 Mg m⁻³
M_r = 1135.20	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 13112 reflections
a = 12.8217 (4) Å	θ = 2.4–33.0°
c = 26.5684 (9) Å	µ = 0.67 mm⁻¹
V = 3782.6 (3) Å³	T = 170 K
Z = 3	Prism, clear colourless
F(000) = 1752	0.2 × 0.2 × 0.15 mm

Data collection top

XtaLAB Mini diffractometer	1545 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 25.3°, θ_min = 2.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −15→15
T_min = 0.914, T_max = 1.000	k = −15→15
11238 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0393P)² + 4.8988P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1545 reflections	Δρ_max = 0.30 e Å⁻³
117 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.57812 (14)	0.42465 (14)	0.46049 (6)	0.0306 (3)
H1	0.516846	0.343592	0.466025	0.037*
N1	0.61267 (12)	0.46273 (12)	0.41383 (5)	0.0307 (3)
O1	0.56235 (10)	0.38624 (11)	0.37552 (4)	0.0362 (3)
Zn1	0.666667	0.333333	0.333333	0.03070 (15)
C2	0.63025 (14)	0.50170 (15)	0.50200 (6)	0.0319 (4)
C3	0.59763 (17)	0.45964 (18)	0.55216 (6)	0.0405 (4)
H3	0.538797	0.378022	0.558427	0.049*
C4	0.6517 (2)	0.5376 (2)	0.59144 (7)	0.0517 (5)
H4	0.630487	0.509631	0.625046	0.062*
C5	0.7383 (2)	0.6590 (2)	0.58245 (8)	0.0561 (6)
H5	0.774576	0.711886	0.610150	0.067*
C6	0.77093 (18)	0.70187 (19)	0.53467 (8)	0.0489 (5)
H6	0.829315	0.784090	0.529361	0.059*
C7	0.71806 (15)	0.62420 (15)	0.49288 (7)	0.0363 (4)
C8	0.74836 (16)	0.66040 (15)	0.44206 (7)	0.0393 (4)
H8	0.805433	0.741987	0.434702	0.047*
C9	0.69756 (16)	0.58101 (15)	0.40386 (7)	0.0367 (4)
H9	0.720339	0.606689	0.370095	0.044*
Cl1	1.000000	1.000000	0.38486 (3)	0.03933 (19)
O2	1.000000	1.000000	0.43897 (9)	0.0641 (7)
O3	0.9353 (2)	0.88066 (16)	0.36730 (7)	0.1013 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0301 (8)	0.0300 (8)	0.0354 (8)	0.0177 (7)	0.0042 (6)	0.0021 (6)
N1	0.0319 (7)	0.0323 (7)	0.0308 (7)	0.0183 (6)	0.0013 (5)	−0.0015 (5)
O1	0.0361 (6)	0.0409 (7)	0.0315 (6)	0.0191 (5)	−0.0016 (5)	−0.0074 (5)
Zn1	0.03368 (18)	0.03368 (18)	0.0248 (2)	0.01684 (9)	0.000	0.000
C2	0.0352 (8)	0.0367 (9)	0.0333 (8)	0.0251 (7)	0.0012 (6)	−0.0008 (7)
C3	0.0509 (10)	0.0499 (10)	0.0355 (9)	0.0364 (9)	0.0041 (8)	0.0028 (8)
C4	0.0705 (14)	0.0764 (15)	0.0340 (9)	0.0560 (13)	−0.0039 (9)	−0.0049 (9)
C5	0.0670 (14)	0.0700 (14)	0.0467 (11)	0.0457 (12)	−0.0180 (10)	−0.0249 (10)
C6	0.0466 (11)	0.0447 (11)	0.0599 (13)	0.0263 (9)	−0.0103 (9)	−0.0183 (9)
C7	0.0356 (9)	0.0357 (9)	0.0439 (10)	0.0226 (7)	−0.0020 (7)	−0.0059 (7)
C8	0.0379 (9)	0.0289 (8)	0.0506 (10)	0.0163 (7)	0.0052 (8)	0.0022 (7)
C9	0.0395 (9)	0.0342 (9)	0.0383 (9)	0.0198 (8)	0.0081 (7)	0.0072 (7)
Cl1	0.0419 (3)	0.0419 (3)	0.0343 (4)	0.02093 (13)	0.000	0.000
O2	0.0798 (12)	0.0798 (12)	0.0326 (13)	0.0399 (6)	0.000	0.000
O3	0.148 (2)	0.0507 (10)	0.0655 (11)	0.0199 (11)	−0.0338 (12)	−0.0110 (8)

Geometric parameters (Å, º) top

C1—H1	0.9500	C5—H5	0.9500
C1—N1	1.325 (2)	C5—C6	1.363 (3)
C1—C2	1.407 (2)	C6—H6	0.9500
N1—O1	1.3346 (17)	C6—C7	1.417 (3)
N1—C9	1.380 (2)	C7—C8	1.418 (3)
O1—Zn1	2.1008 (11)	C8—H8	0.9500
C2—C3	1.420 (2)	C8—C9	1.352 (3)
C2—C7	1.423 (2)	C9—H9	0.9500
C3—H3	0.9500	Cl1—O2	1.438 (2)
C3—C4	1.370 (3)	Cl1—O3ⁱ	1.4063 (18)
C4—H4	0.9500	Cl1—O3ⁱⁱ	1.4062 (18)
C4—C5	1.408 (3)	Cl1—O3	1.4063 (18)

N1—C1—H1	119.3	C4—C3—C2	119.50 (19)
N1—C1—C2	121.39 (15)	C4—C3—H3	120.3
C2—C1—H1	119.3	C3—C4—H4	119.7
C1—N1—O1	119.54 (13)	C3—C4—C5	120.60 (19)
C1—N1—C9	121.29 (14)	C5—C4—H4	119.7
O1—N1—C9	119.15 (13)	C4—C5—H5	119.4
N1—O1—Zn1	119.49 (9)	C6—C5—C4	121.12 (18)
O1ⁱⁱⁱ—Zn1—O1^iv	85.82 (4)	C6—C5—H5	119.4
O1^v—Zn1—O1^vi	85.82 (4)	C5—C6—H6	119.9
O1^v—Zn1—O1^iv	180.0	C5—C6—C7	120.2 (2)
O1^vii—Zn1—O1	180.00 (6)	C7—C6—H6	119.9
O1^vii—Zn1—O1^iv	85.82 (4)	C6—C7—C2	118.61 (17)
O1ⁱⁱⁱ—Zn1—O1	85.82 (4)	C6—C7—C8	124.03 (17)
O1^iv—Zn1—O1	94.18 (4)	C8—C7—C2	117.36 (15)
O1^vi—Zn1—O1^iv	94.18 (4)	C7—C8—H8	119.4
O1^vii—Zn1—O1^v	94.18 (4)	C9—C8—C7	121.24 (16)
O1^v—Zn1—O1	85.82 (4)	C9—C8—H8	119.4
O1^vii—Zn1—O1ⁱⁱⁱ	94.18 (4)	N1—C9—H9	119.9
O1^vi—Zn1—O1	94.18 (4)	C8—C9—N1	120.12 (16)
O1^v—Zn1—O1ⁱⁱⁱ	94.18 (4)	C8—C9—H9	119.9
O1^vii—Zn1—O1^vi	85.82 (4)	O3ⁱⁱ—Cl1—O2	109.37 (8)
O1ⁱⁱⁱ—Zn1—O1^vi	180.0	O3ⁱ—Cl1—O2	109.37 (8)
C1—C2—C3	121.52 (16)	O3—Cl1—O2	109.37 (8)
C1—C2—C7	118.53 (15)	O3—Cl1—O3ⁱ	109.58 (8)
C3—C2—C7	119.95 (16)	O3ⁱⁱ—Cl1—O3	109.58 (8)
C2—C3—H3	120.3	O3ⁱⁱ—Cl1—O3ⁱ	109.57 (8)

C1—N1—O1—Zn1	−112.28 (13)	C2—C7—C8—C9	−1.3 (2)
C1—N1—C9—C8	0.8 (2)	C3—C2—C7—C6	−0.2 (2)
C1—C2—C3—C4	179.35 (15)	C3—C2—C7—C8	178.97 (15)
C1—C2—C7—C6	−179.82 (15)	C3—C4—C5—C6	−0.2 (3)
C1—C2—C7—C8	−0.7 (2)	C4—C5—C6—C7	−0.2 (3)
N1—C1—C2—C3	−176.87 (15)	C5—C6—C7—C2	0.4 (3)
N1—C1—C2—C7	2.8 (2)	C5—C6—C7—C8	−178.66 (18)
O1—N1—C9—C8	179.02 (15)	C6—C7—C8—C9	177.79 (17)
C2—C1—N1—O1	178.91 (13)	C7—C2—C3—C4	−0.3 (2)
C2—C1—N1—C9	−2.9 (2)	C7—C8—C9—N1	1.3 (3)
C2—C3—C4—C5	0.5 (3)	C9—N1—O1—Zn1	69.45 (16)

Symmetry codes: (i) −x+y+1, −x+2, z; (ii) −y+2, x−y+1, z; (iii) y+1/3, −x+y+2/3, −z+2/3; (iv) −x+y+1, −x+1, z; (v) x−y+1/3, x−1/3, −z+2/3; (vi) −y+1, x−y, z; (vii) −x+4/3, −y+2/3, −z+2/3.

Pentaaqua(isoquinoline N-oxide-κO)zinc(II) dinitrate–isoquinoline N-oxide (1/2) (V) top

Crystal data top

[Zn(C₉H₇NO)(H₂O)₅](NO₃)₂·2C₉H₇NO	Z = 2
M_r = 714.94	F(000) = 740
Triclinic, P1	D_x = 1.553 Mg m⁻³
a = 9.7360 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5910 (9) Å	Cell parameters from 5791 reflections
c = 14.6381 (10) Å	θ = 1.9–31.6°
α = 74.352 (6)°	µ = 0.88 mm⁻¹
β = 74.620 (7)°	T = 170 K
γ = 81.633 (7)°	Plank, clear whiteish colourless
V = 1528.8 (2) Å³	0.7 × 0.2 × 0.04 mm

Data collection top

XtaLAB Mini diffractometer	5599 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 25.4°, θ_min = 2.1°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −11→11
T_min = 0.752, T_max = 1.000	k = −13→13
13628 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0476P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5599 reflections	Δρ_max = 0.51 e Å⁻³
464 parameters	Δρ_min = −0.48 e Å⁻³
10 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.38957 (4)	0.27598 (3)	0.47321 (2)	0.02573 (12)
O5	0.2972 (3)	0.1986 (2)	0.62110 (16)	0.0336 (5)
O2	0.2233 (2)	−0.03662 (19)	0.45547 (14)	0.0317 (5)
O8	0.5068 (3)	0.3482 (2)	0.32840 (17)	0.0335 (5)
O6	0.4139 (3)	0.1109 (2)	0.44532 (17)	0.0320 (5)
O1	0.1881 (2)	0.3151 (2)	0.43902 (14)	0.0329 (5)
O3	0.2216 (2)	0.63601 (19)	0.43681 (15)	0.0315 (5)
O7	0.5973 (3)	0.2419 (2)	0.5086 (2)	0.0403 (6)
O4	0.3663 (3)	0.4362 (2)	0.50705 (18)	0.0371 (6)
O9	0.6657 (2)	0.0528 (2)	0.32553 (16)	0.0426 (6)
N2	0.1959 (3)	−0.0507 (2)	0.37417 (17)	0.0254 (6)
O10	0.6236 (3)	0.1957 (2)	0.20239 (17)	0.0494 (7)
N1	0.1475 (3)	0.2886 (2)	0.36717 (17)	0.0259 (6)
N3	0.1843 (3)	0.6184 (2)	0.35969 (17)	0.0242 (6)
O14	0.6846 (3)	0.5678 (2)	0.15635 (16)	0.0506 (7)
N5	0.6688 (3)	0.6144 (3)	0.22466 (18)	0.0319 (6)
O12	0.6239 (3)	0.5538 (2)	0.31066 (16)	0.0550 (8)
N4	0.6547 (3)	0.0879 (3)	0.23757 (19)	0.0348 (7)
O13	0.6984 (3)	0.7187 (2)	0.21242 (18)	0.0561 (7)
C21	0.0981 (3)	0.5780 (3)	0.2055 (2)	0.0266 (7)
C8	0.1928 (3)	0.2520 (3)	0.2088 (2)	0.0274 (7)
C27	0.2819 (3)	0.6092 (3)	0.2792 (2)	0.0286 (7)
H27	0.379243	0.616684	0.275509	0.034*
C18	0.3008 (3)	−0.0639 (3)	0.2975 (2)	0.0296 (7)
H18	0.396900	−0.061642	0.299782	0.036*
C10	0.0545 (3)	−0.0545 (3)	0.3745 (2)	0.0302 (7)
H10	−0.019054	−0.045432	0.430116	0.036*
O11	0.6767 (4)	0.0133 (3)	0.1888 (2)	0.0847 (11)
C26	0.2442 (3)	0.5885 (3)	0.1985 (2)	0.0263 (7)
C12	0.1282 (3)	−0.0853 (3)	0.2112 (2)	0.0297 (7)
C17	0.2723 (3)	−0.0813 (3)	0.2125 (2)	0.0286 (7)
C19	0.0419 (3)	0.6089 (3)	0.3690 (2)	0.0287 (7)
H19	−0.026227	0.616785	0.427344	0.034*
C1	0.0028 (3)	0.2796 (3)	0.3813 (2)	0.0307 (7)
H1	−0.061138	0.287856	0.441167	0.037*
C3	0.0448 (3)	0.2453 (3)	0.2200 (2)	0.0299 (7)
C9	0.2384 (3)	0.2747 (3)	0.2853 (2)	0.0290 (7)
H9	0.337290	0.280238	0.277881	0.035*
C11	0.0214 (3)	−0.0713 (3)	0.2949 (2)	0.0326 (8)
H11	−0.075967	−0.073691	0.295508	0.039*
C20	−0.0004 (3)	0.5883 (3)	0.2944 (2)	0.0297 (7)
H20	−0.098808	0.580508	0.301656	0.036*
C2	−0.0479 (4)	0.2589 (3)	0.3095 (2)	0.0340 (8)
H2	−0.147556	0.253496	0.319718	0.041*
C4	−0.0010 (4)	0.2278 (3)	0.1409 (2)	0.0374 (8)
H4	−0.099689	0.223752	0.146368	0.045*
C22	0.0597 (3)	0.5589 (3)	0.1248 (2)	0.0323 (7)
H22	−0.037509	0.551670	0.128068	0.039*
C23	0.1620 (4)	0.5507 (3)	0.0416 (2)	0.0373 (8)
H23	0.135062	0.536953	−0.012121	0.045*
C25	0.3475 (3)	0.5804 (3)	0.1117 (2)	0.0362 (8)
H25	0.445364	0.587591	0.106691	0.043*
C6	0.2425 (4)	0.2205 (3)	0.0467 (2)	0.0375 (8)
H6	0.308229	0.210789	−0.012074	0.045*
C16	0.3825 (4)	−0.0944 (3)	0.1304 (2)	0.0382 (8)
H16	0.479439	−0.092808	0.131277	0.046*
C13	0.0982 (4)	−0.1022 (3)	0.1265 (2)	0.0385 (8)
H13	0.002163	−0.105780	0.124593	0.046*
C5	0.0964 (4)	0.2167 (3)	0.0569 (2)	0.0391 (9)
H5	0.064065	0.206086	0.004116	0.047*
C7	0.2916 (4)	0.2382 (3)	0.1211 (2)	0.0334 (8)
H7	0.390965	0.241266	0.113941	0.040*
C24	0.3058 (4)	0.5622 (3)	0.0347 (2)	0.0397 (8)
H24	0.375070	0.557385	−0.023941	0.048*
C14	0.2070 (4)	−0.1135 (3)	0.0474 (2)	0.0422 (9)
H14	0.185987	−0.124268	−0.009398	0.051*
C15	0.3490 (4)	−0.1093 (3)	0.0494 (2)	0.0433 (9)
H15	0.423278	−0.116850	−0.006267	0.052*
H6A	0.487 (3)	0.088 (3)	0.410 (2)	0.057 (13)*
H5A	0.295 (4)	0.233 (3)	0.665 (2)	0.046 (11)*
H8A	0.556 (3)	0.307 (3)	0.291 (2)	0.055 (13)*
H5B	0.313 (4)	0.1248 (18)	0.641 (3)	0.056 (13)*
H6B	0.356 (3)	0.066 (3)	0.446 (2)	0.039 (10)*
H7A	0.628 (4)	0.286 (3)	0.533 (2)	0.041 (11)*
H8B	0.543 (4)	0.411 (2)	0.323 (3)	0.062 (13)*
H7B	0.649 (4)	0.179 (2)	0.515 (3)	0.073 (15)*
H4A	0.318 (4)	0.497 (3)	0.486 (3)	0.079 (16)*
H4B	0.380 (4)	0.436 (4)	0.5592 (18)	0.062 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0289 (2)	0.0246 (2)	0.0272 (2)	−0.00353 (15)	−0.00874 (15)	−0.00943 (15)
O5	0.0441 (14)	0.0312 (14)	0.0257 (12)	−0.0052 (11)	−0.0049 (11)	−0.0094 (11)
O2	0.0361 (13)	0.0362 (13)	0.0286 (12)	−0.0091 (10)	−0.0067 (10)	−0.0154 (10)
O8	0.0376 (14)	0.0332 (14)	0.0310 (13)	−0.0127 (12)	−0.0019 (11)	−0.0109 (12)
O6	0.0265 (13)	0.0299 (13)	0.0437 (14)	−0.0074 (11)	−0.0004 (11)	−0.0207 (11)
O1	0.0291 (12)	0.0521 (14)	0.0277 (12)	0.0048 (10)	−0.0136 (10)	−0.0240 (11)
O3	0.0353 (12)	0.0362 (13)	0.0333 (12)	0.0011 (10)	−0.0177 (10)	−0.0184 (10)
O7	0.0365 (14)	0.0334 (15)	0.0669 (18)	0.0000 (12)	−0.0282 (13)	−0.0248 (14)
O4	0.0617 (17)	0.0267 (13)	0.0347 (14)	0.0051 (12)	−0.0296 (13)	−0.0138 (11)
O9	0.0489 (15)	0.0452 (15)	0.0289 (13)	0.0084 (12)	−0.0068 (11)	−0.0096 (11)
N2	0.0308 (14)	0.0208 (13)	0.0268 (14)	−0.0059 (11)	−0.0067 (11)	−0.0077 (11)
O10	0.0631 (18)	0.0388 (15)	0.0385 (14)	0.0056 (13)	−0.0096 (12)	−0.0038 (12)
N1	0.0270 (14)	0.0292 (14)	0.0253 (14)	0.0007 (11)	−0.0102 (11)	−0.0104 (11)
N3	0.0291 (14)	0.0204 (13)	0.0276 (14)	0.0007 (11)	−0.0121 (11)	−0.0096 (11)
O14	0.0637 (17)	0.0682 (18)	0.0293 (13)	−0.0233 (14)	−0.0041 (12)	−0.0247 (13)
N5	0.0268 (15)	0.0460 (18)	0.0272 (15)	−0.0063 (13)	−0.0118 (12)	−0.0089 (14)
O12	0.083 (2)	0.0668 (18)	0.0223 (13)	−0.0474 (16)	−0.0046 (13)	−0.0080 (12)
N4	0.0354 (16)	0.0355 (17)	0.0294 (16)	−0.0090 (13)	0.0006 (12)	−0.0058 (14)
O13	0.097 (2)	0.0361 (15)	0.0424 (15)	−0.0149 (14)	−0.0265 (15)	−0.0065 (12)
C21	0.0288 (17)	0.0226 (16)	0.0313 (17)	0.0012 (13)	−0.0132 (14)	−0.0070 (14)
C8	0.0389 (19)	0.0210 (16)	0.0245 (16)	−0.0027 (14)	−0.0121 (14)	−0.0046 (13)
C27	0.0242 (16)	0.0278 (17)	0.0367 (18)	0.0002 (13)	−0.0101 (14)	−0.0110 (15)
C18	0.0246 (17)	0.0276 (17)	0.0344 (18)	−0.0055 (13)	−0.0015 (14)	−0.0075 (14)
C10	0.0247 (17)	0.0311 (17)	0.0336 (18)	−0.0062 (14)	−0.0042 (14)	−0.0067 (15)
O11	0.168 (4)	0.0488 (18)	0.0441 (17)	−0.010 (2)	−0.028 (2)	−0.0203 (15)
C26	0.0245 (16)	0.0235 (16)	0.0329 (17)	0.0024 (13)	−0.0089 (13)	−0.0104 (14)
C12	0.0318 (18)	0.0245 (16)	0.0323 (18)	−0.0048 (14)	−0.0075 (14)	−0.0047 (14)
C17	0.0306 (17)	0.0220 (16)	0.0315 (17)	−0.0034 (14)	−0.0037 (14)	−0.0069 (14)
C19	0.0253 (17)	0.0304 (17)	0.0313 (17)	−0.0019 (14)	−0.0069 (14)	−0.0092 (14)
C1	0.0293 (17)	0.0373 (19)	0.0275 (17)	−0.0056 (15)	−0.0066 (14)	−0.0098 (15)
C3	0.0359 (18)	0.0279 (17)	0.0292 (17)	−0.0090 (14)	−0.0134 (15)	−0.0035 (14)
C9	0.0251 (16)	0.0349 (18)	0.0295 (17)	0.0009 (14)	−0.0094 (14)	−0.0111 (15)
C11	0.0219 (16)	0.0377 (19)	0.0390 (19)	−0.0019 (14)	−0.0085 (14)	−0.0096 (16)
C20	0.0246 (16)	0.0345 (18)	0.0337 (18)	−0.0035 (14)	−0.0094 (14)	−0.0115 (15)
C2	0.0335 (18)	0.0388 (19)	0.0330 (18)	−0.0101 (15)	−0.0115 (15)	−0.0068 (15)
C4	0.045 (2)	0.041 (2)	0.0338 (19)	−0.0122 (17)	−0.0184 (16)	−0.0090 (16)
C22	0.0318 (18)	0.0378 (19)	0.0324 (18)	0.0015 (15)	−0.0126 (15)	−0.0145 (15)
C23	0.047 (2)	0.039 (2)	0.0336 (19)	0.0067 (16)	−0.0180 (16)	−0.0176 (16)
C25	0.0308 (18)	0.0361 (19)	0.043 (2)	0.0015 (15)	−0.0074 (15)	−0.0161 (16)
C6	0.058 (2)	0.0306 (18)	0.0248 (17)	0.0026 (17)	−0.0122 (16)	−0.0096 (15)
C16	0.0348 (19)	0.039 (2)	0.0378 (19)	−0.0065 (16)	0.0015 (15)	−0.0118 (16)
C13	0.045 (2)	0.039 (2)	0.0347 (19)	−0.0059 (17)	−0.0138 (16)	−0.0092 (16)
C5	0.060 (2)	0.0361 (19)	0.0305 (18)	−0.0088 (18)	−0.0225 (18)	−0.0098 (16)
C7	0.0382 (19)	0.0356 (19)	0.0260 (17)	0.0022 (15)	−0.0086 (14)	−0.0082 (15)
C24	0.042 (2)	0.042 (2)	0.0340 (19)	0.0036 (17)	−0.0017 (16)	−0.0191 (17)
C14	0.061 (3)	0.040 (2)	0.0288 (19)	−0.0065 (18)	−0.0103 (17)	−0.0139 (16)
C15	0.056 (2)	0.042 (2)	0.0298 (19)	−0.0083 (18)	0.0004 (17)	−0.0133 (16)

Geometric parameters (Å, º) top

Zn1—O5	2.110 (2)	C18—C17	1.414 (4)
Zn1—O8	2.130 (2)	C10—H10	0.9500
Zn1—O6	2.030 (2)	C10—C11	1.355 (4)
Zn1—O1	2.1078 (19)	C26—C25	1.413 (4)
Zn1—O7	2.174 (2)	C12—C17	1.415 (4)
Zn1—O4	2.015 (2)	C12—C11	1.411 (4)
O5—H5A	0.833 (18)	C12—C13	1.415 (4)
O5—H5B	0.833 (18)	C17—C16	1.409 (4)
O2—N2	1.341 (3)	C19—H19	0.9500
O8—H8A	0.827 (18)	C19—C20	1.352 (4)
O8—H8B	0.832 (19)	C1—H1	0.9500
O6—H6A	0.820 (18)	C1—C2	1.361 (4)
O6—H6B	0.816 (18)	C3—C2	1.414 (4)
O1—N1	1.337 (3)	C3—C4	1.417 (4)
O3—N3	1.346 (3)	C9—H9	0.9500
O7—H7A	0.815 (18)	C11—H11	0.9500
O7—H7B	0.819 (19)	C20—H20	0.9500
O4—H4A	0.821 (19)	C2—H2	0.9500
O4—H4B	0.807 (18)	C4—H4	0.9500
O9—N4	1.270 (3)	C4—C5	1.363 (5)
N2—C18	1.328 (4)	C22—H22	0.9500
N2—C10	1.383 (4)	C22—C23	1.369 (4)
O10—N4	1.242 (3)	C23—H23	0.9500
N1—C1	1.384 (4)	C23—C24	1.400 (5)
N1—C9	1.321 (4)	C25—H25	0.9500
N3—C27	1.322 (4)	C25—C24	1.369 (4)
N3—C19	1.375 (4)	C6—H6	0.9500
O14—N5	1.225 (3)	C6—C5	1.396 (5)
N5—O12	1.261 (3)	C6—C7	1.372 (4)
N5—O13	1.239 (3)	C16—H16	0.9500
N4—O11	1.226 (3)	C16—C15	1.369 (5)
C21—C26	1.420 (4)	C13—H13	0.9500
C21—C20	1.420 (4)	C13—C14	1.368 (4)
C21—C22	1.408 (4)	C5—H5	0.9500
C8—C3	1.418 (4)	C7—H7	0.9500
C8—C9	1.406 (4)	C24—H24	0.9500
C8—C7	1.417 (4)	C14—H14	0.9500
C27—H27	0.9500	C14—C15	1.398 (5)
C27—C26	1.412 (4)	C15—H15	0.9500
C18—H18	0.9500

Cg1···Cg4	3.839 (2)	Cg2···Cg8	3.969 (2)
Cg1···Cg7	3.893 (2)	Cg4···Cg7ⁱ	3.943 (2)
Cg1···Cg8	3.8500 (19)	Cg5···Cg7ⁱ	3.7374 (19)
Cg2···Cg4	3.6617 (19)	Cg5···Cg8ⁱ	3.968 (2)
Cg2···Cg5	3.823 (2)

O5—Zn1—O8	173.16 (9)	C11—C12—C17	117.9 (3)
O5—Zn1—O7	88.42 (10)	C11—C12—C13	123.3 (3)
O8—Zn1—O7	84.75 (10)	C13—C12—C17	118.8 (3)
O6—Zn1—O5	89.30 (10)	C18—C17—C12	118.2 (3)
O6—Zn1—O8	90.14 (10)	C16—C17—C18	121.9 (3)
O6—Zn1—O1	92.38 (9)	C16—C17—C12	119.9 (3)
O6—Zn1—O7	89.52 (9)	N3—C19—H19	120.2
O1—Zn1—O5	91.94 (9)	C20—C19—N3	119.5 (3)
O1—Zn1—O8	94.90 (9)	C20—C19—H19	120.2
O1—Zn1—O7	178.06 (9)	N1—C1—H1	120.0
O4—Zn1—O5	88.47 (10)	C2—C1—N1	120.0 (3)
O4—Zn1—O8	91.93 (10)	C2—C1—H1	120.0
O4—Zn1—O6	177.42 (10)	C2—C3—C8	117.4 (3)
O4—Zn1—O1	88.98 (9)	C2—C3—C4	124.3 (3)
O4—Zn1—O7	89.13 (10)	C4—C3—C8	118.3 (3)
Zn1—O5—H5A	121 (2)	N1—C9—C8	121.9 (3)
Zn1—O5—H5B	117 (3)	N1—C9—H9	119.0
H5A—O5—H5B	110 (4)	C8—C9—H9	119.1
Zn1—O8—H8A	125 (3)	C10—C11—C12	121.5 (3)
Zn1—O8—H8B	113 (3)	C10—C11—H11	119.2
H8A—O8—H8B	113 (4)	C12—C11—H11	119.2
Zn1—O6—H6A	121 (3)	C21—C20—H20	119.1
Zn1—O6—H6B	132 (2)	C19—C20—C21	121.8 (3)
H6A—O6—H6B	103 (4)	C19—C20—H20	119.1
N1—O1—Zn1	128.04 (16)	C1—C2—C3	121.2 (3)
Zn1—O7—H7A	123 (2)	C1—C2—H2	119.4
Zn1—O7—H7B	129 (3)	C3—C2—H2	119.4
H7A—O7—H7B	106 (4)	C3—C4—H4	119.9
Zn1—O4—H4A	127 (3)	C5—C4—C3	120.1 (3)
Zn1—O4—H4B	116 (3)	C5—C4—H4	119.9
H4A—O4—H4B	112 (4)	C21—C22—H22	119.9
O2—N2—C10	117.3 (2)	C23—C22—C21	120.3 (3)
C18—N2—O2	121.3 (2)	C23—C22—H22	119.9
C18—N2—C10	121.3 (3)	C22—C23—H23	119.5
O1—N1—C1	116.4 (2)	C22—C23—C24	120.9 (3)
C9—N1—O1	122.7 (2)	C24—C23—H23	119.5
C9—N1—C1	120.8 (3)	C26—C25—H25	120.2
O3—N3—C19	117.3 (2)	C24—C25—C26	119.6 (3)
C27—N3—O3	120.8 (2)	C24—C25—H25	120.2
C27—N3—C19	121.9 (3)	C5—C6—H6	119.8
O14—N5—O12	119.3 (3)	C7—C6—H6	119.8
O14—N5—O13	122.2 (3)	C7—C6—C5	120.4 (3)
O13—N5—O12	118.5 (3)	C17—C16—H16	120.2
O10—N4—O9	120.2 (3)	C15—C16—C17	119.6 (3)
O11—N4—O9	118.4 (3)	C15—C16—H16	120.2
O11—N4—O10	121.4 (3)	C12—C13—H13	119.9
C20—C21—C26	117.1 (3)	C14—C13—C12	120.2 (3)
C22—C21—C26	118.6 (3)	C14—C13—H13	119.9
C22—C21—C20	124.3 (3)	C4—C5—C6	121.5 (3)
C9—C8—C3	118.7 (3)	C4—C5—H5	119.2
C9—C8—C7	121.1 (3)	C6—C5—H5	119.2
C7—C8—C3	120.2 (3)	C8—C7—H7	120.3
N3—C27—H27	119.4	C6—C7—C8	119.4 (3)
N3—C27—C26	121.2 (3)	C6—C7—H7	120.3
C26—C27—H27	119.4	C23—C24—H24	119.7
N2—C18—H18	119.3	C25—C24—C23	120.6 (3)
N2—C18—C17	121.4 (3)	C25—C24—H24	119.7
C17—C18—H18	119.3	C13—C14—H14	119.7
N2—C10—H10	120.2	C13—C14—C15	120.6 (3)
C11—C10—N2	119.6 (3)	C15—C14—H14	119.7
C11—C10—H10	120.2	C16—C15—C14	121.0 (3)
C27—C26—C21	118.5 (3)	C16—C15—H15	119.5
C27—C26—C25	121.6 (3)	C14—C15—H15	119.5
C25—C26—C21	119.9 (3)

Zn1—O1—N1—C1	155.2 (2)	C17—C16—C15—C14	−0.9 (5)
Zn1—O1—N1—C9	−26.6 (4)	C19—N3—C27—C26	−0.3 (4)
O2—N2—C18—C17	178.6 (3)	C1—N1—C9—C8	0.9 (5)
O2—N2—C10—C11	−178.5 (3)	C3—C8—C9—N1	0.7 (5)
O1—N1—C1—C2	176.7 (3)	C3—C8—C7—C6	1.1 (5)
O1—N1—C9—C8	−177.2 (3)	C3—C4—C5—C6	0.9 (5)
O3—N3—C27—C26	178.8 (2)	C9—N1—C1—C2	−1.5 (5)
O3—N3—C19—C20	−178.4 (3)	C9—C8—C3—C2	−1.6 (4)
N2—C18—C17—C12	−0.5 (4)	C9—C8—C3—C4	177.2 (3)
N2—C18—C17—C16	179.4 (3)	C9—C8—C7—C6	−177.6 (3)
N2—C10—C11—C12	0.1 (5)	C11—C12—C17—C18	0.1 (4)
N1—C1—C2—C3	0.5 (5)	C11—C12—C17—C16	−179.7 (3)
N3—C27—C26—C21	0.2 (4)	C11—C12—C13—C14	179.1 (3)
N3—C27—C26—C25	179.0 (3)	C20—C21—C26—C27	−0.4 (4)
N3—C19—C20—C21	−1.0 (5)	C20—C21—C26—C25	−179.3 (3)
C21—C26—C25—C24	−0.1 (5)	C20—C21—C22—C23	179.7 (3)
C21—C22—C23—C24	−0.7 (5)	C2—C3—C4—C5	179.4 (3)
C8—C3—C2—C1	1.0 (5)	C4—C3—C2—C1	−177.7 (3)
C8—C3—C4—C5	0.6 (5)	C22—C21—C26—C27	179.2 (3)
C27—N3—C19—C20	0.7 (4)	C22—C21—C26—C25	0.3 (4)
C27—C26—C25—C24	−179.0 (3)	C22—C21—C20—C19	−178.7 (3)
C18—N2—C10—C11	−0.5 (4)	C22—C23—C24—C25	0.9 (5)
C18—C17—C16—C15	−179.0 (3)	C13—C12—C17—C18	179.8 (3)
C10—N2—C18—C17	0.6 (4)	C13—C12—C17—C16	−0.1 (5)
C26—C21—C20—C19	0.9 (4)	C13—C12—C11—C10	−179.6 (3)
C26—C21—C22—C23	0.1 (5)	C13—C14—C15—C16	0.3 (5)
C26—C25—C24—C23	−0.5 (5)	C5—C6—C7—C8	0.3 (5)
C12—C17—C16—C15	0.8 (5)	C7—C8—C3—C2	179.6 (3)
C12—C13—C14—C15	0.5 (5)	C7—C8—C3—C4	−1.6 (4)
C17—C12—C11—C10	0.0 (5)	C7—C8—C9—N1	179.5 (3)
C17—C12—C13—C14	−0.6 (5)	C7—C6—C5—C4	−1.4 (5)

Symmetry code: (i) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O9	0.82 (2)	1.91 (2)	2.723 (3)	173 (4)
O5—H5A···O13ⁱⁱ	0.83 (2)	2.04 (2)	2.861 (3)	168 (3)
O8—H8A···O10	0.83 (2)	2.00 (2)	2.808 (3)	164 (4)
O5—H5B···O9ⁱⁱⁱ	0.83 (2)	1.98 (2)	2.802 (3)	171 (4)
O6—H6B···O2	0.82 (2)	1.84 (2)	2.651 (3)	177 (3)
O7—H7A···O3ⁱⁱ	0.82 (2)	2.03 (2)	2.798 (3)	156 (3)
O8—H8B···O12	0.83 (2)	1.88 (2)	2.710 (3)	179 (4)
O7—H7B···O2ⁱⁱⁱ	0.82 (2)	1.94 (2)	2.755 (3)	173 (4)
O4—H4A···O3	0.82 (2)	1.81 (2)	2.634 (3)	176 (5)
O4—H4B···O12ⁱⁱ	0.81 (2)	1.93 (2)	2.729 (3)	169 (4)

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Contributions of selected intermolecular contacts (%) to the Hirshfeld surfaces of (I)–(V) top

Compound	(I)	(II)	(III)	(IV)	(V)
H···H	30.9	27.8	28.0	41.8	40.6
H···X/X···H	29.0	30.9	31.1	–	–
C···H/H···C	13.3	20.1	17.2	22.0	8.6
C···C	11.3	6.6	7.0	6.0	8.5
O···H/H···O	8.8	8.3	7.9	24.5	37.6

Acknowledgements

The authors thank the Department of Biochemistry, Chemistry, and Physics at Georgia Southern University for the financial support of this work.

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of zinc(II) coordination complexes with iso­quinoline N-oxide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structures of zinc(II) coordination complexes with isoquinoline N-oxide

3. Supramolecular features