Five new bis(arylamide)dichloridozinc(II) complexes have been prepared and characterized. All of the complexes contain hydrogen bonds between the amide N—H group and the amide carbonyl oxygen atoms or the chlorine atoms, forming extended networks.
Keywords: ionic co-crystal, co-crystal salt, zinc(II) chloride, benzamide, toluamide
Abstract
Ionic co-crystals are co-crystals between organic molecules and inorganic salt coformers. Co-crystals of pharmaceuticals are of interest to help control polymorph formation and potentially improve stability and other physical properties. We describe the preparation, crystal structures, and hydrogen bonding of five different 2:1 benzamide or toluamide/zinc(II) chloride co-crystal salts, namely, bis(benzamide-κO)dichloridozinc(II), [ZnCl2(C7H7NO)2], dichloridobis(2-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], dichloridobis(3-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], dichloridobis(4-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], and dichloridobis(4-hydroxybenzamide-κO)zinc(II), [ZnCl2(C7H7NO2)2]. All of the complexes contain hydrogen bonds between the amide N—H group and the amide carbonyl oxygen atoms or the chlorine atoms, forming extended networks.
Chemical context
Ionic co-crystals, formed from the combination of inorganic salts and organic molecules, are of interest for their ability to promote or stabilize crystal forms of organic or pharmaceutical molecules (Braga et al., 2011 ▸, 2018 ▸). The chloride salts of magnesium, calcium, and strontium have been shown to form an extensive range of structure types when co-crystallized with drug molecules such as piracetam (Braga et al., 2011 ▸; Song et al., 2018 ▸), etiracetam and levitiracetam (Song et al., 2019 ▸, 2020 ▸), and nicotinamide and isonicotinamide (Braga et al., 2011 ▸; Song et al., 2020 ▸). Sodium bromide and sodium iodide form ionic co-crystals with carbamazepine (Buist & Kennedy, 2014 ▸). More recently, it has been shown that co-crystallization with ionic salts can produce chirally resolved forms when combining lithium halides with l- and dl-histidine (Braga et al., 2016 ▸), magnesium chloride with RS-oxiracetam (Shemchuk et al., 2020 ▸), and zinc chloride with RS-etiracetam (Shemchuk et al., 2018 ▸). Co-crystallization of nefiracetam with zinc chloride produced products with improved solubility and dissolution rates (Buol et al., 2020 ▸).
The current study was undertaken to explore the preparation of ionic co-crystals (alternatively termed co-crystal salts; Grothe, et al., 2016 ▸) using zinc chloride combined with various organic amides (specifically benzamide, 4-hydroxybenzamide, and toluamide) that can serve as models of pharmaceutical molecules.
Structural commentary
Five new zinc complexes, (1) through (5), have been prepared and structurally characterized. All five complexes are 2:1 O-bonded aryl amide:ZnCl2 complexes with approximately tetrahedral zinc(II) centers. The complexes crystallize in five different space groups and form hydrogen-bonding interactions between the amide N—H groups and either an amide oxygen or a zinc-bound chlorido ligand.
Compound (1), bis(benzamide-κO)dichloridozinc(II), [ZnCl2(C7H7NO)2], crystallizes in the P21/n space group with two independent molecules in the asymmetric unit and displays one N—H⋯O and one N—H⋯Cl intramolecular hydrogen bond in each molecule (see Fig. 1 ▸ and Table 1 ▸). A search for non-crystallographic symmetry using PLATON (Spek, 2020 ▸) shows the two independent zinc complexes are related by a rotation of −173.2° and translation by 7.232 Å along the vector [1.000 0.101 0.992]. Alignment of the two residues gave a weighted r.m.s. fit of 0.330 Å.
Figure 1.
Displacement ellipsoid (50%) diagram and atom-numbering scheme of the two independent molecules in (1). N—H⋯O contacts are shown in red and N—H⋯Cl contacts are shown in green.
Table 1. Hydrogen-bond geometry (Å, °) for (1) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1A—H1AA⋯O2A | 0.84 (2) | 2.12 (2) | 2.888 (2) | 152 (3) |
| N1A—H1AB⋯Cl1B i | 0.87 (2) | 2.56 (2) | 3.3644 (15) | 153 (2) |
| N2A—H2AA⋯Cl1A | 0.87 (2) | 2.51 (2) | 3.3281 (15) | 155 (2) |
| N2A—H2AB⋯Cl2A ii | 0.85 (2) | 2.51 (2) | 3.3404 (15) | 164 (2) |
| N1B—H1BA⋯O2B | 0.84 (2) | 2.17 (2) | 2.911 (2) | 147 (2) |
| N1B—H1BB⋯Cl1A | 0.88 (2) | 2.51 (2) | 3.3682 (16) | 167 (2) |
| N2B—H2BA⋯Cl1B | 0.85 (2) | 2.57 (2) | 3.3085 (15) | 146 (2) |
| N2B—H2BB⋯Cl2B iii | 0.85 (2) | 2.48 (2) | 3.3107 (15) | 165 (2) |
Symmetry codes: (i) x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}; (ii) -x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}; (iii) -x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}.
As shown in Fig. 2 ▸, compound (2), dichloridobis(2-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], displays two intramolecular N—H⋯Cl hydrogen bonds to one chlorine atom (see Table 2 ▸) and crystallizes in the P21 space group. Compound (3), dichloridobis(3-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], crystallizes in the C2/c space group with the zinc atom lying on the twofold axis (see Fig. 3 ▸) and, unlike the other compounds in this study, compound (3) does not form any intramolecular hydrogen bonds. Compound (4), dichloridobis(4-methylbenzamide-κO)zinc(II), [ZnCl2(C8H9NO)2], crystallizes in the P21/c space group and compound (5), dichloridobis(4-hydroxybenzamide-κO)zinc(II), [ZnCl2(C7H7NO2)2], crystallizes in the Cc space group and both compounds form two intramolecular hydrogen bonds, one N—H⋯O and one N—H⋯Cl, similar to the interactions found in compound (1) (see Figs. 4 ▸ and 5 ▸ and Tables 4 ▸ and 5 ▸).
Figure 2.
Displacement ellipsoid (50%) diagram and atom-numbering scheme for (2). N—H⋯Cl contacts are shown in green.
Table 2. Hydrogen-bond geometry (Å, °) for (2) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1A⋯Cl2i | 0.82 (2) | 2.57 (2) | 3.2916 (17) | 147 (2) |
| N1—H1B⋯Cl1 | 0.86 (2) | 2.54 (2) | 3.3077 (17) | 150 (2) |
| N2—H2A⋯Cl1 | 0.85 (2) | 2.52 (2) | 3.2667 (16) | 148 (2) |
| N2—H2B⋯O1ii | 0.84 (2) | 2.14 (2) | 2.949 (2) | 163 (2) |
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z.
Figure 3.
Displacement ellipsoid (50%) diagram and atom-numbering scheme for (3). The minor component of the disordered methyl group is not shown for clarity.
Figure 4.
Displacement ellipsoid (50%) diagram and atom-numbering scheme for (4). The N—H⋯O contact is shown in red and the N—H⋯Cl contact is shown in green.
Figure 5.
Displacement ellipsoid (50%) diagram and atom numbering scheme for (5). The N—H⋯O contact is shown in red and the N—H⋯Cl contact is shown in green.
Table 4. Hydrogen-bond geometry (Å, °) for (4) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1A⋯O2 | 0.87 (2) | 2.07 (2) | 2.8753 (19) | 154 (2) |
| N1—H1B⋯Cl2i | 0.86 (2) | 2.49 (2) | 3.2265 (14) | 145 (2) |
| N2—H2A⋯Cl1ii | 0.86 (2) | 2.50 (2) | 3.2956 (16) | 155 (2) |
| N2—H2B⋯Cl2 | 0.87 (2) | 3.05 (2) | 3.6341 (17) | 126 (2) |
Symmetry codes: (i) x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}; (ii) x-1, y, z.
Table 5. Hydrogen-bond geometry (Å, °) for (5) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O3—H3⋯Cl1i | 0.84 (3) | 2.64 (4) | 3.322 (3) | 140 (5) |
| O3—H3⋯Cl2ii | 0.84 (3) | 2.75 (4) | 3.349 (3) | 130 (4) |
| O4—H4⋯Cl2iii | 0.80 (3) | 2.33 (3) | 3.131 (3) | 175 (6) |
| N1—H1A⋯Cl1 | 0.86 (3) | 2.93 (4) | 3.648 (4) | 142 (4) |
| N1—H1B⋯Cl1iv | 0.87 (3) | 2.61 (3) | 3.479 (4) | 173 (4) |
| N2—H2A⋯O1 | 0.84 (3) | 2.15 (3) | 2.924 (5) | 154 (5) |
| N2—H2B⋯Cl2v | 0.84 (3) | 2.77 (4) | 3.405 (4) | 135 (5) |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x+{\script{1\over 2}}, y-{\script{1\over 2}}, z; (iv) x, -y+2, z+{\script{1\over 2}}; (v) x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}.
A comparison of selected bond lengths and bond angles for all five complexes is given in Table 6 ▸. The average zinc–chlorine distance of 2.224 (13) Å compares well with the average of 2.22 (2) Å observed for 27 similar four-coordinate ZnCl2 L 2 complexes (with L = carbonyl oxygen donating ligand) found in a search of the CSD (Version 5.42, May 2021; Groom et al., 2016 ▸). A similar agreement is found for the zinc–oxygen distance with both averages at 1.98 (2) Å. The bond angles in the complexes in this study display an average Cl—Zn—Cl angle of 117 (5)° and an average O—Zn—O angle of 101 (3)°, again quite close to the average angles of 119 (4) and 100 (7)° for the set of comparable molecules.
Table 6. Selected bond lengths and angles (Å, °) for compounds (1) through (5).
| Compound | R / position | Zn—Cl1 | Zn—Cl2 | Zn—O1 | Zn—O2 | Cl—Zn—Cl | O—Zn—O |
|---|---|---|---|---|---|---|---|
| (1)a | H | 2.2294 (4) | 2.2118 (4) | 1.9653 (12) | 2.0040 (13) | 113.726 (18) | 99.75 (5) |
| (1)b | H | 2.2361 (4) | 2.2107 (4) | 1.9632 (12) | 2.0089 (13) | 114.034 (18) | 101.44 (5) |
| (2) | CH3 / ortho | 2.2340 (4) | 2.1947 (5) | 2.0169 (13) | 1.9781 (11) | 125.120 (19) | 103.92 (5) |
| (3)c | CH3 / meta | 2.2341 (4) | 2.2341 (4) | 1.9652 (10) | 1.9652 (10) | 121.25 (2) | 96.12 (6) |
| (4) | CH3 / para | 2.2166 (5) | 2.2170 (5) | 1.9592 (12) | 2.0191 (11) | 115.836 (17) | 101.98 (5) |
| (5) | OH / para | 2.2347 (11) | 2.2305 (11) | 1.980 (3) | 1.954 (3) | 112.84 (4) | 101.21 (12) |
Notes: (a) molecule 1; (b) molecule 2; (c) O1/O2 and Cl1/Cl2 related by symmetry.
Supramolecular features
Each compound displays a unique hydrogen-bonding network, consisting primarily of N—H⋯O and N—H⋯Cl interactions, summarized in Table 1 ▸ through 5. In addition to four intramolecular hydrogen bonds, compound (1) forms four N—H⋯Cl intermolecular hydrogen bonds (two from each independent molecule), forming an extended network as shown in Fig. 6 ▸ and summarized in Table 1 ▸. Compound (2) also utilizes N—H bonds in hydrogen-bonding interactions, two intramolecular and two intermolecular, to form layers within the structure (see Fig. 7 ▸ and Table 2 ▸). Only intermolecular N—H⋯Cl hydrogen bonds are found in compound (3) (shown in Fig. 8 ▸, two interactions per asymmetric unit, four per molecule, see Table 3 ▸) and they combine to form chains that run parallel to the c axis. Compound (4) forms two N—H⋯Cl intermolecular contacts in addition to the two intramolecular hydrogen bonds, resulting in a complex set of layers that run perpendicular to the b axis (see Fig. 9 ▸ and Table 4 ▸). The addition of the 4-hydroxy group in compound (5) results in the greatest number of hydrogen bonds among this set of complexes, as shown in Fig. 10 ▸ and summarized in Table 5 ▸, with two N—H⋯Cl and three O—H⋯Cl intermolecular interactions per molecule.
Figure 6.
Packing diagram of (1) (viewed along b) showing N—H⋯O contacts (red) and N—H⋯Cl contacts (green).
Figure 7.
Packing diagram of (2) (viewed along b) showing N—H⋯O contacts (red) and N—H⋯Cl contacts (green).
Figure 8.
Packing diagram of (3) (viewed along [101]) showing N—H⋯Cl contacts (green). The minor component of the disordered methyl group is not shown for clarity.
Table 3. Hydrogen-bond geometry (Å, °) for (3) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1A⋯Cl1i | 0.85 (2) | 2.56 (2) | 3.2854 (13) | 145 (2) |
| N1—H1B⋯Cl1ii | 0.85 (2) | 2.52 (2) | 3.2979 (13) | 153 (2) |
Symmetry codes: (i) x, -y+1, z-{\script{1\over 2}}; (ii) x, y, z-1.
Figure 9.
Packing diagram of (4) (viewed along a) showing N—H⋯O contacts (red) and N—H⋯Cl contacts (green).
Figure 10.
Packing diagram of (5) (viewed along a) showing N—H⋯O contacts (red) and N—H⋯Cl contacts (green).
Compounds (1), (3), and (5) form π–π interactions between the benzene rings of the benzamide or toluamide groups as summarized in Table 7 ▸. No significant π–π interactions were found for compounds (2) or (4).
Table 7. Summary of π–π interactions (Å, °) in compounds (1), (3), and (5).
α is the dihedral angle between planes. Cg is the centroid of the benzene ring of the benzamide or toluamide molecule.
| Compound | Ring i | Ring j | Cg⋯Cg distance | α |
|---|---|---|---|---|
| (1) | 1 | 4i | 3.9522 (11) | 8.76 (9) |
| (1) | 1 | 4ii | 3.8781 (11) | 8.76 (9) |
| (1) | 3 | 2iii | 3.8195 (10) | 6.27 (8) |
| (3) | 1 | 1iv | 3.7770 (10) | 6.86 (7) |
| (5) | 1 | 2v | 3.760 (3) | 8.0 (2) |
Symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, 2 − y, 1 − z; (iii) {3\over 2} − x, −{1\over 2} + y, {1\over 2} − z; (iv) 1 − x, y, {1\over 2} − z; (v) −{1\over 2} + x, {3\over 2} − y, {1\over 2} + z.
Database survey
A search of the CSD (Version 5.42, May 2021; Groom et al., 2016 ▸) produced a relatively small number of amide-coordinated zinc(II)chloride complexes. One of the earliest is a dichloridobis(dma)zinc(II) complex (CSD refcode: DMAMZN10; Herceg & Fischer, 1974 ▸; dma = N,N-dimethylacetamide). The similar dichloridobis(dmf)zinc(II) (KOBWIH; Suzuki et al., 1991 ▸; dmf = N,N-dimethylformamide) has also been reported. Edwards et al. (1999 ▸, 1998 ▸) investigated the structures of a series of ZnX 2 L 2 complexes that included L = dmf and X = Br and I (FIQBEM, FEXWIO, respectively), the latter of which undergoes a reversible phase transition at 228 K (Edwards et al., 1998 ▸). A similar study (Turnbull et al., 2000 ▸) compared the structures of ZnX 2(dma)2 where X = Cl, Br, I (DMAMZN11, CAHWEO, CAHWAK, respectively). As part of a larger study, Smirnov et al. (2014 ▸) prepared and crystallographically characterized dimethylurea complexes of zinc(II)chloride and zinc(II)bromide (ZZZSAG01, COQXIR) along with bis(piperidine-1-carboxamide) zinc(II)halide complexes (COQWOW, COQVIP), all of which display intramolecular N—H⋯O hydrogen bonding similar to that observed in this study.
A number of zinc(II) iodide complexes, ZnI2 L 2, have been prepared with simple amide ligands, including urea (ACAQAW; Furmanova et al., 2001 ▸), acetamide (VIDBOA; Savinkina et al., 2007 ▸), and formamide (DIYGUO; Savinkina et al., 2008 ▸). Savinkina et al. (2009 ▸) have also prepared a series of ZnI2 L 2 complexes with L = dimethylurea (VUCTUJ), thioacetamide (VUCTOD), and benzamide (VUCVAR).
Three structural studies have prepared zinc(II)chloride complexes with pharmaceutically relevant molecules. Sultana et al. (2016 ▸) prepared bis(4′-methoxyacetanilide)dichloridozinc(II) (EQIGOC). Dichloridobis(nicotinamide)zinc(II) has also been studied (WUKZAD; İde et al., 2002 ▸) but differs from the structures in this report in that the two nicotinamide ligands are N-bonded through the ring nitrogen instead of the amide oxygen. Buol et al. (2020 ▸) describe the preparation and crystal structures of co-crystals obtained from the co-crystallization of nefiracetam with zinc(II)chloride, producing two different structures. In one form (CCDC 2010272), the four-coordinate zinc atom binds to one nefiracetam molecule (via the γ-lactam carbonyl), one water molecule, and two chlorido ligands. In the second form (CCDC 2010264), the zinc bonds to one nefiracetam molecule through the γ-lactam and to a second via the amide carbonyl, forming a cyclic zinc dimer.
Synthesis and crystallization
All reagents were used as received from the manufacturer. Compounds (1) through (5) were prepared by dissolution of the respective components in various solvents [50:50 v:v ratio of water and ethanol (benzamide, 4-hydroxybenzamide), ethanol (o,m,p-toluamide)] followed by slow evaporation. In a typical preparation, a 1:1 stoichiometric ratio of benzamide (0.1352 g) and zinc(II) chloride (0.1336 g) was dissolved in approximately 5 mL of a 50:50 v:v ratio of water and ethanol. Slow evaporation of the resulting solution produced single crystals of compound (1).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 8 ▸. All hydrogen atoms were located in difference maps.
Table 8. Experimental details.
| (1) | (2) | (3) | (4) | (5) | |
|---|---|---|---|---|---|
| Crystal data | |||||
| Chemical formula | [ZnCl2(C7H7NO)2] | [ZnCl2(C8H9NO)2] | [ZnCl2(C8H9NO)2] | [ZnCl2(C8H9NO)2] | [ZnCl2(C7H7NO2)2] |
| M r | 378.54 | 406.59 | 406.59 | 406.59 | 410.54 |
| Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21 | Monoclinic, C2/c | Monoclinic, P21/c | Monoclinic, C c |
| Temperature (K) | 100 | 100 | 100 | 100 | 100 |
| a, b, c (Å) | 20.6241 (11), 7.3309 (4), 20.6485 (11) | 7.3802 (3), 8.2491 (3), 14.5953 (5) | 13.9452 (11), 18.9742 (16), 7.0651 (6) | 6.8376 (4), 17.2694 (9), 14.9856 (7) | 7.0532 (6), 21.3776 (17), 11.1181 (9) |
| β (°) | 90.532 (1) | 97.852 (1) | 108.021 (2) | 96.893 (2) | 106.477 (2) |
| V (Å3) | 3121.8 (3) | 880.23 (6) | 1777.7 (3) | 1756.73 (16) | 1607.5 (2) |
| Z | 8 | 2 | 4 | 4 | 4 |
| Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
| μ (mm−1) | 1.92 | 1.71 | 1.69 | 1.71 | 1.88 |
| Crystal size (mm) | 0.6 × 0.60 × 0.35 | 0.5 × 0.16 × 0.11 | 0.42 × 0.14 × 0.14 | 0.56 × 0.18 × 0.09 | 0.15 × 0.09 × 0.07 |
| Data collection | |||||
| Diffractometer | Bruker APEXII CCD | Bruker APEXII CCD | Bruker APEXII CCD | Bruker APEXII CCD | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.558, 0.746 | 0.478, 0.680 | 0.620, 0.746 | 0.629, 0.746 | 0.673, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 48491, 9668, 9501 | 20749, 5348, 5135 | 12177, 2295, 2023 | 33806, 5376, 4283 | 17255, 4168, 3809 |
| R int | 0.023 | 0.025 | 0.027 | 0.051 | 0.042 |
| (sin θ/λ)max (Å−1) | 0.718 | 0.714 | 0.676 | 0.715 | 0.676 |
| Refinement | |||||
| R[F2 > 2σ(F 2)], wR(F 2), S | 0.022, 0.053, 1.07 | 0.018, 0.039, 1.00 | 0.022, 0.059, 1.05 | 0.031, 0.069, 1.01 | 0.030, 0.065, 1.05 |
| No. of reflections | 9668 | 5348 | 2295 | 5376 | 4168 |
| No. of parameters | 404 | 223 | 113 | 222 | 227 |
| No. of restraints | 8 | 5 | 17 | 4 | 8 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.43, −0.35 | 0.31, −0.24 | 0.39, −0.26 | 0.46, −0.32 | 0.46, −0.29 |
| Absolute structure | – | Refined as an inversion twin. | – | – | Refined as an inversion twin |
| Absolute structure parameter | – | 0.016 (6) | – | – | 0.024 (13) |
All carbon-bonded H atoms were placed in idealized positions using a riding model with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å and U iso(H) = 1.2U eq(C) (aromatic) or U iso(H) = 1.5U eq(C) (methyl). All amide H-atom positions were refined with N—H distances restrained to 0.88 (2) Å and Uiso(H) = 1.5Ueq(N). The hydroxyl H-atom positions in compound (5) were refined with O—H distances restrained to 0.84 (2) Å and U iso(H) = 1.5U eq(N).
Compound (1) was refined as a pseudo-merohedral twin (monoclinic mimicking orthorhombic, since β is close to 90°) with a twin law of (0 0 −1 0 −1 0 −1 0 0) , corresponding to a twofold rotation about the [10
] axis. The twin ratio refined to 0.4825 (5).
The methyl group in compound (3) was modeled as a disordered methyl group with each set of hydrogen atoms rotated by 60° (AFIX 127). The disorder was identified from multiple peaks near C8 in the difference map. The refined occupancies of the two hydrogen atom sets were 0.54 (2):0.46 (2).
Supplementary Material
Crystal structure: contains datablock(s) global, 1, 2, 3, 4, 5. DOI: 10.1107/S2056989021008264/zl5023sup1.cif
Structure factors: contains datablock(s) 1. DOI: 10.1107/S2056989021008264/zl50231sup2.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50231sup7.mol
Structure factors: contains datablock(s) 2. DOI: 10.1107/S2056989021008264/zl50232sup3.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50232sup8.mol
Structure factors: contains datablock(s) 3. DOI: 10.1107/S2056989021008264/zl50233sup4.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50233sup9.mol
Supporting information file. DOI: 10.1107/S2056989021008264/zl50234sup10.mol
Structure factors: contains datablock(s) 4. DOI: 10.1107/S2056989021008264/zl50234sup5.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50235sup11.mol
Structure factors: contains datablock(s) 5. DOI: 10.1107/S2056989021008264/zl50235sup6.hkl
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Bis(benzamide-κO)dichloridozinc(II) (1) . Crystal data
| [ZnCl2(C7H7NO)2] | F(000) = 1536 |
| Mr = 378.54 | Dx = 1.611 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 20.6241 (11) Å | Cell parameters from 9702 reflections |
| b = 7.3309 (4) Å | θ = 6.8–30.5° |
| c = 20.6485 (11) Å | µ = 1.92 mm−1 |
| β = 90.532 (1)° | T = 100 K |
| V = 3121.8 (3) Å3 | Block, clear light colourless |
| Z = 8 | 0.6 × 0.60 × 0.35 mm |
Bis(benzamide-κO)dichloridozinc(II) (1) . Data collection
| Bruker APEXII CCD diffractometer | 9668 independent reflections |
| Radiation source: sealed tube | 9501 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.023 |
| Detector resolution: 8 pixels mm-1 | θmax = 30.7°, θmin = 1.0° |
| ω and φ scans | h = −29→27 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −10→10 |
| Tmin = 0.558, Tmax = 0.746 | l = −29→29 |
| 48491 measured reflections |
Bis(benzamide-κO)dichloridozinc(II) (1) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.022 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.053 | w = 1/[σ2(Fo2) + (0.0256P)2 + 1.2394P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.002 |
| 9668 reflections | Δρmax = 0.43 e Å−3 |
| 404 parameters | Δρmin = −0.34 e Å−3 |
| 8 restraints |
Bis(benzamide-κO)dichloridozinc(II) (1) . Special details
| 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. |
| Refinement. Refined as a 2-component twin. |
Bis(benzamide-κO)dichloridozinc(II) (1) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1A | 0.62741 (2) | 0.74478 (4) | 0.34018 (2) | 0.01179 (4) | |
| Cl1A | 0.69397 (2) | 0.97842 (5) | 0.36146 (2) | 0.01636 (7) | |
| Cl2A | 0.66272 (2) | 0.47923 (6) | 0.37699 (2) | 0.02204 (9) | |
| O1A | 0.53865 (6) | 0.78998 (17) | 0.36973 (6) | 0.0163 (2) | |
| O2A | 0.61465 (6) | 0.73870 (17) | 0.24363 (6) | 0.0163 (2) | |
| N1A | 0.48113 (7) | 0.8093 (2) | 0.27621 (8) | 0.0217 (3) | |
| H1AA | 0.5138 (10) | 0.785 (4) | 0.2536 (12) | 0.033* | |
| H1AB | 0.4458 (10) | 0.824 (3) | 0.2534 (11) | 0.033* | |
| N2A | 0.71341 (7) | 0.8269 (2) | 0.21095 (7) | 0.0189 (3) | |
| H2AA | 0.7218 (12) | 0.869 (3) | 0.2497 (9) | 0.028* | |
| H2AB | 0.7417 (10) | 0.851 (3) | 0.1825 (10) | 0.028* | |
| C1A | 0.42560 (7) | 0.8246 (2) | 0.37895 (8) | 0.0138 (3) | |
| C2A | 0.36411 (9) | 0.7932 (2) | 0.35252 (10) | 0.0188 (3) | |
| H2A | 0.359316 | 0.761280 | 0.308143 | 0.023* | |
| C3A | 0.30976 (9) | 0.8092 (3) | 0.39175 (11) | 0.0251 (4) | |
| H3A | 0.267689 | 0.788739 | 0.374069 | 0.030* | |
| C4A | 0.31709 (9) | 0.8548 (3) | 0.45663 (10) | 0.0257 (4) | |
| H4A | 0.279853 | 0.865296 | 0.483113 | 0.031* | |
| C5A | 0.37808 (9) | 0.8854 (3) | 0.48331 (9) | 0.0245 (4) | |
| H5A | 0.382768 | 0.916605 | 0.527769 | 0.029* | |
| C6A | 0.43205 (8) | 0.8700 (2) | 0.44430 (8) | 0.0188 (3) | |
| H6A | 0.473993 | 0.890556 | 0.462261 | 0.023* | |
| C7A | 0.48516 (7) | 0.8061 (2) | 0.34012 (8) | 0.0137 (3) | |
| C8A | 0.63351 (8) | 0.7328 (2) | 0.13053 (8) | 0.0129 (3) | |
| C9A | 0.67309 (8) | 0.7703 (2) | 0.07743 (8) | 0.0156 (3) | |
| H9A | 0.715796 | 0.815424 | 0.084231 | 0.019* | |
| C10A | 0.64995 (9) | 0.7416 (2) | 0.01464 (9) | 0.0190 (3) | |
| H10A | 0.676912 | 0.767083 | −0.021295 | 0.023* | |
| C11A | 0.58777 (9) | 0.6760 (2) | 0.00452 (8) | 0.0201 (3) | |
| H11A | 0.572142 | 0.656193 | −0.038327 | 0.024* | |
| C12A | 0.54825 (8) | 0.6391 (2) | 0.05687 (8) | 0.0201 (3) | |
| H12A | 0.505440 | 0.595321 | 0.049643 | 0.024* | |
| C13A | 0.57073 (8) | 0.6657 (2) | 0.11984 (8) | 0.0163 (3) | |
| H13A | 0.543606 | 0.638474 | 0.155497 | 0.020* | |
| C14A | 0.65448 (8) | 0.7671 (2) | 0.19832 (8) | 0.0129 (3) | |
| Zn1B | 0.83932 (2) | 0.71554 (2) | 0.62742 (2) | 0.01256 (4) | |
| Cl1B | 0.86157 (2) | 0.48139 (6) | 0.69283 (2) | 0.01790 (8) | |
| Cl2B | 0.87722 (2) | 0.97969 (6) | 0.66307 (2) | 0.02414 (8) | |
| O1B | 0.86683 (6) | 0.67828 (17) | 0.53751 (6) | 0.0176 (2) | |
| O2B | 0.74288 (6) | 0.71225 (17) | 0.61469 (6) | 0.0171 (2) | |
| N1B | 0.77974 (8) | 0.7747 (2) | 0.48074 (8) | 0.0190 (3) | |
| H1BA | 0.7583 (12) | 0.791 (3) | 0.5147 (10) | 0.028* | |
| H1BB | 0.7610 (11) | 0.815 (3) | 0.4453 (9) | 0.028* | |
| N2B | 0.71169 (7) | 0.6279 (2) | 0.71506 (7) | 0.0201 (3) | |
| H2BA | 0.7511 (8) | 0.612 (3) | 0.7260 (11) | 0.030* | |
| H2BB | 0.6836 (10) | 0.585 (3) | 0.7407 (10) | 0.030* | |
| C1B | 0.87943 (7) | 0.7032 (2) | 0.42412 (8) | 0.0134 (3) | |
| C2B | 0.85410 (10) | 0.7395 (2) | 0.36242 (9) | 0.0191 (3) | |
| H2B | 0.810046 | 0.775075 | 0.357395 | 0.023* | |
| C3B | 0.89345 (10) | 0.7234 (3) | 0.30844 (9) | 0.0231 (4) | |
| H3B | 0.876266 | 0.747726 | 0.266478 | 0.028* | |
| C4B | 0.95793 (9) | 0.6716 (3) | 0.31582 (9) | 0.0229 (3) | |
| H4B | 0.984945 | 0.661451 | 0.278984 | 0.028* | |
| C5B | 0.98268 (8) | 0.6349 (2) | 0.37696 (9) | 0.0221 (3) | |
| H5B | 1.026722 | 0.599079 | 0.381792 | 0.027* | |
| C6B | 0.94395 (7) | 0.6499 (2) | 0.43130 (8) | 0.0165 (3) | |
| H6B | 0.961289 | 0.623994 | 0.473079 | 0.020* | |
| C7B | 0.84054 (8) | 0.7192 (2) | 0.48449 (8) | 0.0133 (3) | |
| C8B | 0.63040 (7) | 0.6729 (2) | 0.63094 (8) | 0.0135 (3) | |
| C9B | 0.57871 (8) | 0.6850 (2) | 0.67379 (8) | 0.0176 (3) | |
| H9B | 0.586500 | 0.697499 | 0.718986 | 0.021* | |
| C10B | 0.51568 (8) | 0.6786 (3) | 0.64956 (8) | 0.0189 (3) | |
| H10B | 0.480096 | 0.687201 | 0.678286 | 0.023* | |
| C11B | 0.50456 (8) | 0.6597 (2) | 0.58355 (8) | 0.0196 (3) | |
| H11B | 0.461330 | 0.655944 | 0.567321 | 0.024* | |
| C12B | 0.55602 (8) | 0.6463 (3) | 0.54103 (8) | 0.0197 (3) | |
| H12B | 0.548141 | 0.632735 | 0.495882 | 0.024* | |
| C13B | 0.61889 (8) | 0.6528 (2) | 0.56485 (8) | 0.0164 (3) | |
| H13B | 0.654323 | 0.643623 | 0.535959 | 0.020* | |
| C14B | 0.69873 (8) | 0.6727 (2) | 0.65418 (8) | 0.0151 (3) |
Bis(benzamide-κO)dichloridozinc(II) (1) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1A | 0.00847 (10) | 0.01580 (8) | 0.01112 (10) | 0.00076 (6) | 0.00080 (5) | 0.00048 (6) |
| Cl1A | 0.01556 (17) | 0.01763 (16) | 0.01590 (17) | −0.00279 (13) | 0.00038 (13) | −0.00214 (13) |
| Cl2A | 0.01553 (18) | 0.02015 (18) | 0.0306 (2) | 0.00577 (13) | 0.00699 (15) | 0.00859 (15) |
| O1A | 0.0097 (5) | 0.0253 (6) | 0.0139 (5) | 0.0034 (4) | −0.0001 (4) | −0.0007 (4) |
| O2A | 0.0124 (6) | 0.0253 (6) | 0.0112 (6) | −0.0021 (4) | 0.0016 (4) | −0.0004 (4) |
| N1A | 0.0101 (6) | 0.0408 (9) | 0.0143 (7) | 0.0017 (6) | 0.0003 (5) | 0.0039 (6) |
| N2A | 0.0108 (6) | 0.0342 (8) | 0.0118 (6) | −0.0019 (5) | 0.0012 (4) | −0.0034 (5) |
| C1A | 0.0101 (6) | 0.0145 (7) | 0.0169 (7) | 0.0014 (5) | 0.0035 (5) | 0.0027 (5) |
| C2A | 0.0098 (8) | 0.0244 (8) | 0.0221 (9) | −0.0006 (6) | 0.0017 (6) | 0.0051 (7) |
| C3A | 0.0095 (7) | 0.0296 (9) | 0.0362 (11) | 0.0009 (6) | 0.0040 (7) | 0.0075 (8) |
| C4A | 0.0174 (8) | 0.0252 (9) | 0.0348 (10) | 0.0037 (7) | 0.0140 (7) | 0.0029 (7) |
| C5A | 0.0230 (8) | 0.0269 (9) | 0.0238 (8) | 0.0021 (7) | 0.0106 (6) | −0.0049 (7) |
| C6A | 0.0143 (7) | 0.0217 (8) | 0.0206 (8) | 0.0018 (6) | 0.0041 (6) | −0.0027 (6) |
| C7A | 0.0095 (6) | 0.0150 (7) | 0.0166 (7) | 0.0007 (5) | 0.0020 (5) | 0.0014 (5) |
| C8A | 0.0122 (7) | 0.0160 (7) | 0.0104 (6) | 0.0026 (5) | −0.0005 (5) | −0.0011 (5) |
| C9A | 0.0127 (7) | 0.0215 (8) | 0.0125 (7) | 0.0033 (5) | 0.0017 (5) | −0.0002 (5) |
| C10A | 0.0198 (8) | 0.0233 (8) | 0.0140 (7) | 0.0062 (6) | 0.0012 (6) | 0.0000 (6) |
| C11A | 0.0231 (8) | 0.0223 (8) | 0.0149 (7) | 0.0043 (6) | −0.0027 (6) | −0.0039 (6) |
| C12A | 0.0189 (7) | 0.0218 (8) | 0.0194 (8) | −0.0022 (6) | −0.0035 (6) | −0.0047 (6) |
| C13A | 0.0165 (7) | 0.0178 (7) | 0.0146 (7) | −0.0012 (6) | 0.0006 (5) | −0.0022 (5) |
| C14A | 0.0108 (7) | 0.0166 (7) | 0.0114 (7) | 0.0024 (5) | −0.0002 (5) | 0.0000 (5) |
| Zn1B | 0.01035 (10) | 0.01706 (8) | 0.01029 (10) | 0.00033 (6) | 0.00080 (6) | −0.00034 (6) |
| Cl1B | 0.01485 (17) | 0.01905 (17) | 0.01981 (19) | 0.00226 (12) | −0.00040 (14) | 0.00404 (13) |
| Cl2B | 0.0299 (2) | 0.02135 (17) | 0.0213 (2) | −0.00772 (15) | 0.00810 (15) | −0.00662 (14) |
| O1B | 0.0148 (5) | 0.0277 (6) | 0.0103 (5) | 0.0031 (5) | 0.0004 (4) | −0.0016 (4) |
| O2B | 0.0104 (6) | 0.0269 (6) | 0.0140 (6) | 0.0009 (4) | 0.0028 (4) | 0.0032 (4) |
| N1B | 0.0126 (7) | 0.0326 (8) | 0.0117 (7) | 0.0026 (5) | 0.0015 (5) | 0.0016 (5) |
| N2B | 0.0114 (6) | 0.0358 (8) | 0.0130 (6) | 0.0005 (6) | 0.0010 (5) | 0.0033 (6) |
| C1B | 0.0126 (7) | 0.0150 (7) | 0.0126 (7) | −0.0014 (5) | 0.0023 (5) | −0.0019 (5) |
| C2B | 0.0194 (9) | 0.0240 (8) | 0.0139 (8) | 0.0010 (6) | 0.0000 (6) | 0.0001 (6) |
| C3B | 0.0279 (10) | 0.0283 (9) | 0.0133 (8) | 0.0025 (7) | 0.0047 (7) | 0.0015 (6) |
| C4B | 0.0282 (9) | 0.0234 (8) | 0.0173 (8) | 0.0013 (7) | 0.0108 (6) | −0.0004 (6) |
| C5B | 0.0186 (8) | 0.0254 (8) | 0.0225 (8) | 0.0015 (6) | 0.0077 (6) | −0.0033 (6) |
| C6B | 0.0133 (7) | 0.0197 (7) | 0.0164 (7) | 0.0011 (6) | 0.0030 (5) | −0.0017 (6) |
| C7B | 0.0120 (7) | 0.0158 (7) | 0.0120 (7) | −0.0023 (5) | 0.0016 (5) | −0.0029 (5) |
| C8B | 0.0108 (6) | 0.0152 (7) | 0.0146 (7) | −0.0008 (5) | 0.0002 (5) | −0.0013 (5) |
| C9B | 0.0140 (7) | 0.0224 (8) | 0.0163 (8) | 0.0008 (6) | 0.0013 (6) | −0.0035 (6) |
| C10B | 0.0108 (7) | 0.0268 (8) | 0.0191 (8) | −0.0014 (6) | 0.0032 (5) | −0.0036 (6) |
| C11B | 0.0120 (7) | 0.0252 (8) | 0.0216 (8) | −0.0039 (6) | −0.0030 (6) | −0.0002 (6) |
| C12B | 0.0166 (7) | 0.0282 (9) | 0.0142 (7) | −0.0051 (6) | −0.0021 (5) | 0.0003 (6) |
| C13B | 0.0143 (7) | 0.0198 (7) | 0.0151 (7) | −0.0029 (6) | 0.0011 (5) | 0.0008 (6) |
| C14B | 0.0129 (7) | 0.0176 (7) | 0.0147 (7) | 0.0009 (6) | 0.0023 (5) | −0.0015 (6) |
Bis(benzamide-κO)dichloridozinc(II) (1) . Geometric parameters (Å, º)
| Zn1A—Cl1A | 2.2361 (4) | Zn1B—Cl1B | 2.2294 (4) |
| Zn1A—Cl2A | 2.2107 (4) | Zn1B—Cl2B | 2.2118 (4) |
| Zn1A—O1A | 1.9632 (12) | Zn1B—O1B | 1.9653 (12) |
| Zn1A—O2A | 2.0089 (13) | Zn1B—O2B | 2.0040 (13) |
| O1A—C7A | 1.2618 (19) | O1B—C7B | 1.254 (2) |
| O2A—C14A | 1.268 (2) | O2B—C14B | 1.2617 (19) |
| N1A—H1AA | 0.842 (16) | N1B—H1BA | 0.842 (16) |
| N1A—H1AB | 0.871 (16) | N1B—H1BB | 0.876 (16) |
| N1A—C7A | 1.322 (2) | N1B—C7B | 1.320 (2) |
| N2A—H2AA | 0.874 (16) | N2B—H2BA | 0.850 (16) |
| N2A—H2AB | 0.851 (16) | N2B—H2BB | 0.848 (16) |
| N2A—C14A | 1.316 (2) | N2B—C14B | 1.324 (2) |
| C1A—C2A | 1.395 (2) | C1B—C2B | 1.398 (2) |
| C1A—C6A | 1.395 (2) | C1B—C6B | 1.393 (2) |
| C1A—C7A | 1.479 (2) | C1B—C7B | 1.493 (2) |
| C2A—H2A | 0.9500 | C2B—H2B | 0.9500 |
| C2A—C3A | 1.394 (3) | C2B—C3B | 1.390 (3) |
| C3A—H3A | 0.9500 | C3B—H3B | 0.9500 |
| C3A—C4A | 1.388 (3) | C3B—C4B | 1.390 (3) |
| C4A—H4A | 0.9500 | C4B—H4B | 0.9500 |
| C4A—C5A | 1.387 (3) | C4B—C5B | 1.384 (3) |
| C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
| C5A—C6A | 1.385 (2) | C5B—C6B | 1.388 (2) |
| C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
| C8A—C9A | 1.400 (2) | C8B—C9B | 1.394 (2) |
| C8A—C13A | 1.401 (2) | C8B—C13B | 1.391 (2) |
| C8A—C14A | 1.483 (2) | C8B—C14B | 1.485 (2) |
| C9A—H9A | 0.9500 | C9B—H9B | 0.9500 |
| C9A—C10A | 1.394 (2) | C9B—C10B | 1.389 (2) |
| C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
| C10A—C11A | 1.384 (3) | C10B—C11B | 1.387 (2) |
| C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
| C11A—C12A | 1.386 (2) | C11B—C12B | 1.387 (2) |
| C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
| C12A—C13A | 1.390 (2) | C12B—C13B | 1.383 (2) |
| C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
| Cl2A—Zn1A—Cl1A | 114.035 (18) | Cl2B—Zn1B—Cl1B | 113.726 (18) |
| O1A—Zn1A—Cl1A | 112.47 (4) | O1B—Zn1B—Cl1B | 113.93 (4) |
| O1A—Zn1A—Cl2A | 110.29 (4) | O1B—Zn1B—Cl2B | 109.38 (4) |
| O1A—Zn1A—O2A | 101.44 (5) | O1B—Zn1B—O2B | 99.75 (5) |
| O2A—Zn1A—Cl1A | 106.65 (4) | O2B—Zn1B—Cl1B | 105.59 (4) |
| O2A—Zn1A—Cl2A | 111.18 (4) | O2B—Zn1B—Cl2B | 113.67 (4) |
| C7A—O1A—Zn1A | 132.74 (11) | C7B—O1B—Zn1B | 131.70 (11) |
| C14A—O2A—Zn1A | 130.46 (11) | C14B—O2B—Zn1B | 129.74 (12) |
| H1AA—N1A—H1AB | 113 (3) | H1BA—N1B—H1BB | 115 (3) |
| C7A—N1A—H1AA | 120 (2) | C7B—N1B—H1BA | 120.1 (18) |
| C7A—N1A—H1AB | 125.9 (18) | C7B—N1B—H1BB | 124.4 (17) |
| H2AA—N2A—H2AB | 115 (2) | H2BA—N2B—H2BB | 116 (2) |
| C14A—N2A—H2AA | 118.3 (16) | C14B—N2B—H2BA | 118.1 (17) |
| C14A—N2A—H2AB | 124.9 (16) | C14B—N2B—H2BB | 123.5 (16) |
| C2A—C1A—C7A | 121.96 (15) | C2B—C1B—C7B | 123.15 (15) |
| C6A—C1A—C2A | 119.73 (15) | C6B—C1B—C2B | 119.91 (15) |
| C6A—C1A—C7A | 118.29 (14) | C6B—C1B—C7B | 116.94 (14) |
| C1A—C2A—H2A | 120.3 | C1B—C2B—H2B | 120.0 |
| C3A—C2A—C1A | 119.46 (19) | C3B—C2B—C1B | 119.91 (18) |
| C3A—C2A—H2A | 120.3 | C3B—C2B—H2B | 120.0 |
| C2A—C3A—H3A | 120.0 | C2B—C3B—H3B | 120.0 |
| C4A—C3A—C2A | 120.01 (18) | C2B—C3B—C4B | 120.03 (18) |
| C4A—C3A—H3A | 120.0 | C4B—C3B—H3B | 120.0 |
| C3A—C4A—H4A | 119.6 | C3B—C4B—H4B | 120.1 |
| C5A—C4A—C3A | 120.86 (16) | C5B—C4B—C3B | 119.84 (16) |
| C5A—C4A—H4A | 119.6 | C5B—C4B—H4B | 120.1 |
| C4A—C5A—H5A | 120.4 | C4B—C5B—H5B | 119.6 |
| C6A—C5A—C4A | 119.12 (18) | C4B—C5B—C6B | 120.80 (16) |
| C6A—C5A—H5A | 120.4 | C6B—C5B—H5B | 119.6 |
| C1A—C6A—H6A | 119.6 | C1B—C6B—H6B | 120.3 |
| C5A—C6A—C1A | 120.81 (16) | C5B—C6B—C1B | 119.50 (16) |
| C5A—C6A—H6A | 119.6 | C5B—C6B—H6B | 120.3 |
| O1A—C7A—N1A | 122.15 (15) | O1B—C7B—N1B | 121.88 (15) |
| O1A—C7A—C1A | 118.20 (15) | O1B—C7B—C1B | 118.61 (14) |
| N1A—C7A—C1A | 119.64 (14) | N1B—C7B—C1B | 119.51 (15) |
| C9A—C8A—C13A | 119.37 (15) | C9B—C8B—C14B | 121.61 (14) |
| C9A—C8A—C14A | 122.60 (15) | C13B—C8B—C9B | 120.32 (15) |
| C13A—C8A—C14A | 117.99 (14) | C13B—C8B—C14B | 118.02 (14) |
| C8A—C9A—H9A | 119.9 | C8B—C9B—H9B | 120.4 |
| C10A—C9A—C8A | 120.11 (16) | C10B—C9B—C8B | 119.19 (16) |
| C10A—C9A—H9A | 119.9 | C10B—C9B—H9B | 120.4 |
| C9A—C10A—H10A | 119.9 | C9B—C10B—H10B | 119.9 |
| C11A—C10A—C9A | 120.13 (17) | C11B—C10B—C9B | 120.19 (16) |
| C11A—C10A—H10A | 119.9 | C11B—C10B—H10B | 119.9 |
| C10A—C11A—H11A | 120.0 | C10B—C11B—H11B | 119.7 |
| C10A—C11A—C12A | 120.05 (16) | C10B—C11B—C12B | 120.57 (15) |
| C12A—C11A—H11A | 120.0 | C12B—C11B—H11B | 119.7 |
| C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 120.2 |
| C11A—C12A—C13A | 120.57 (16) | C13B—C12B—C11B | 119.51 (16) |
| C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 120.2 |
| C8A—C13A—H13A | 120.1 | C8B—C13B—H13B | 119.9 |
| C12A—C13A—C8A | 119.76 (15) | C12B—C13B—C8B | 120.22 (15) |
| C12A—C13A—H13A | 120.1 | C12B—C13B—H13B | 119.9 |
| O2A—C14A—N2A | 120.79 (15) | O2B—C14B—N2B | 122.02 (15) |
| O2A—C14A—C8A | 118.92 (15) | O2B—C14B—C8B | 118.66 (15) |
| N2A—C14A—C8A | 120.29 (14) | N2B—C14B—C8B | 119.31 (14) |
| Zn1A—O1A—C7A—N1A | −6.1 (2) | Zn1B—O1B—C7B—N1B | −11.6 (2) |
| Zn1A—O1A—C7A—C1A | 174.83 (11) | Zn1B—O1B—C7B—C1B | 168.80 (11) |
| Zn1A—O2A—C14A—N2A | −7.2 (2) | Zn1B—O2B—C14B—N2B | 1.6 (3) |
| Zn1A—O2A—C14A—C8A | 173.10 (10) | Zn1B—O2B—C14B—C8B | −177.09 (11) |
| C1A—C2A—C3A—C4A | −0.4 (3) | C1B—C2B—C3B—C4B | −0.1 (3) |
| C2A—C1A—C6A—C5A | −0.4 (3) | C2B—C1B—C6B—C5B | 0.6 (2) |
| C2A—C1A—C7A—O1A | −162.09 (15) | C2B—C1B—C7B—O1B | 177.76 (15) |
| C2A—C1A—C7A—N1A | 18.8 (2) | C2B—C1B—C7B—N1B | −1.9 (2) |
| C2A—C3A—C4A—C5A | 0.1 (3) | C2B—C3B—C4B—C5B | 0.5 (3) |
| C3A—C4A—C5A—C6A | 0.0 (3) | C3B—C4B—C5B—C6B | −0.3 (3) |
| C4A—C5A—C6A—C1A | 0.1 (3) | C4B—C5B—C6B—C1B | −0.3 (3) |
| C6A—C1A—C2A—C3A | 0.5 (3) | C6B—C1B—C2B—C3B | −0.4 (3) |
| C6A—C1A—C7A—O1A | 16.1 (2) | C6B—C1B—C7B—O1B | −2.4 (2) |
| C6A—C1A—C7A—N1A | −162.95 (16) | C6B—C1B—C7B—N1B | 177.91 (15) |
| C7A—C1A—C2A—C3A | 178.72 (16) | C7B—C1B—C2B—C3B | 179.38 (16) |
| C7A—C1A—C6A—C5A | −178.66 (16) | C7B—C1B—C6B—C5B | −179.20 (15) |
| C8A—C9A—C10A—C11A | 0.0 (2) | C8B—C9B—C10B—C11B | 0.2 (3) |
| C9A—C8A—C13A—C12A | −0.7 (2) | C9B—C8B—C13B—C12B | 0.5 (3) |
| C9A—C8A—C14A—O2A | 176.29 (15) | C9B—C8B—C14B—O2B | −160.50 (16) |
| C9A—C8A—C14A—N2A | −3.4 (2) | C9B—C8B—C14B—N2B | 20.8 (3) |
| C9A—C10A—C11A—C12A | 0.2 (3) | C9B—C10B—C11B—C12B | 0.2 (3) |
| C10A—C11A—C12A—C13A | −0.7 (3) | C10B—C11B—C12B—C13B | −0.3 (3) |
| C11A—C12A—C13A—C8A | 0.9 (3) | C11B—C12B—C13B—C8B | 0.0 (3) |
| C13A—C8A—C9A—C10A | 0.2 (2) | C13B—C8B—C9B—C10B | −0.6 (3) |
| C13A—C8A—C14A—O2A | −1.6 (2) | C13B—C8B—C14B—O2B | 22.1 (2) |
| C13A—C8A—C14A—N2A | 178.73 (15) | C13B—C8B—C14B—N2B | −156.62 (16) |
| C14A—C8A—C9A—C10A | −177.62 (15) | C14B—C8B—C9B—C10B | −177.92 (16) |
| C14A—C8A—C13A—C12A | 177.25 (15) | C14B—C8B—C13B—C12B | 177.94 (16) |
Bis(benzamide-κO)dichloridozinc(II) (1) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1A—H1AA···O2A | 0.84 (2) | 2.12 (2) | 2.888 (2) | 152 (3) |
| N1A—H1AB···Cl1Bi | 0.87 (2) | 2.56 (2) | 3.3644 (15) | 153 (2) |
| N2A—H2AA···Cl1A | 0.87 (2) | 2.51 (2) | 3.3281 (15) | 155 (2) |
| N2A—H2AB···Cl2Aii | 0.85 (2) | 2.51 (2) | 3.3404 (15) | 164 (2) |
| N1B—H1BA···O2B | 0.84 (2) | 2.17 (2) | 2.911 (2) | 147 (2) |
| N1B—H1BB···Cl1A | 0.88 (2) | 2.51 (2) | 3.3682 (16) | 167 (2) |
| N2B—H2BA···Cl1B | 0.85 (2) | 2.57 (2) | 3.3085 (15) | 146 (2) |
| N2B—H2BB···Cl2Biii | 0.85 (2) | 2.48 (2) | 3.3107 (15) | 165 (2) |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+3/2.
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Crystal data
| [ZnCl2(C8H9NO)2] | F(000) = 416 |
| Mr = 406.59 | Dx = 1.534 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.3802 (3) Å | Cell parameters from 9884 reflections |
| b = 8.2491 (3) Å | θ = 2.8–30.5° |
| c = 14.5953 (5) Å | µ = 1.71 mm−1 |
| β = 97.852 (1)° | T = 100 K |
| V = 880.23 (6) Å3 | Needle, clear light colourless |
| Z = 2 | 0.5 × 0.16 × 0.11 mm |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Data collection
| Bruker APEXII CCD diffractometer | 5348 independent reflections |
| Radiation source: sealed tube | 5135 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.025 |
| Detector resolution: 8 pixels mm-1 | θmax = 30.5°, θmin = 2.8° |
| ω and φ scans | h = −10→10 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −11→11 |
| Tmin = 0.478, Tmax = 0.680 | l = −20→20 |
| 20749 measured reflections |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Refinement
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.018 | w = 1/[σ2(Fo2) + (0.0078P)2] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.039 | (Δ/σ)max < 0.001 |
| S = 1.00 | Δρmax = 0.31 e Å−3 |
| 5348 reflections | Δρmin = −0.24 e Å−3 |
| 223 parameters | Absolute structure: Refined as an inversion twin. |
| 5 restraints | Absolute structure parameter: 0.016 (6) |
| Primary atom site location: dual |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Special details
| 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. |
| Refinement. Refined as a 2-component inversion twin |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.65448 (2) | 0.68146 (2) | 0.17755 (2) | 0.01057 (5) | |
| Cl1 | 0.47230 (6) | 0.60339 (6) | 0.05028 (3) | 0.01680 (9) | |
| Cl2 | 0.81306 (6) | 0.90729 (5) | 0.19165 (3) | 0.01797 (10) | |
| O1 | 0.85119 (17) | 0.51161 (15) | 0.20425 (9) | 0.0127 (2) | |
| O2 | 0.51677 (14) | 0.66731 (18) | 0.28443 (8) | 0.0146 (2) | |
| N1 | 0.7092 (2) | 0.28760 (19) | 0.14025 (13) | 0.0191 (4) | |
| H1A | 0.719 (3) | 0.190 (3) | 0.1287 (15) | 0.029* | |
| H1B | 0.616 (3) | 0.340 (3) | 0.1134 (17) | 0.029* | |
| N2 | 0.2228 (2) | 0.64887 (18) | 0.21691 (10) | 0.0143 (3) | |
| H2A | 0.253 (3) | 0.665 (3) | 0.1637 (13) | 0.021* | |
| H2B | 0.114 (3) | 0.627 (3) | 0.2209 (15) | 0.021* | |
| C1 | 1.0259 (2) | 0.2690 (2) | 0.20486 (12) | 0.0104 (3) | |
| C2 | 1.1130 (2) | 0.1966 (2) | 0.13538 (11) | 0.0133 (3) | |
| C3 | 1.2723 (2) | 0.1092 (2) | 0.16300 (13) | 0.0169 (4) | |
| H3 | 1.334536 | 0.060513 | 0.117218 | 0.020* | |
| C4 | 1.3429 (2) | 0.0912 (2) | 0.25546 (13) | 0.0177 (4) | |
| H4 | 1.451212 | 0.029817 | 0.272382 | 0.021* | |
| C5 | 1.2548 (2) | 0.1629 (3) | 0.32327 (12) | 0.0163 (4) | |
| H5 | 1.301711 | 0.149691 | 0.386746 | 0.020* | |
| C6 | 1.0978 (2) | 0.2542 (2) | 0.29786 (12) | 0.0128 (3) | |
| H6 | 1.039430 | 0.306526 | 0.343897 | 0.015* | |
| C7 | 0.8535 (2) | 0.3634 (2) | 0.18179 (12) | 0.0109 (3) | |
| C8 | 1.0403 (3) | 0.2111 (3) | 0.03369 (13) | 0.0230 (5) | |
| H8A | 1.139556 | 0.190759 | −0.003126 | 0.034* | |
| H8B | 0.991635 | 0.320424 | 0.020737 | 0.034* | |
| H8C | 0.942754 | 0.131322 | 0.017568 | 0.034* | |
| C9 | 0.2906 (2) | 0.6074 (2) | 0.38067 (11) | 0.0112 (3) | |
| C10 | 0.3975 (2) | 0.5094 (2) | 0.44575 (12) | 0.0136 (3) | |
| C11 | 0.3296 (3) | 0.4755 (2) | 0.52821 (13) | 0.0176 (4) | |
| H11 | 0.397722 | 0.406299 | 0.572177 | 0.021* | |
| C12 | 0.1661 (3) | 0.5397 (2) | 0.54805 (13) | 0.0181 (4) | |
| H12 | 0.124588 | 0.515956 | 0.605376 | 0.022* | |
| C13 | 0.0628 (2) | 0.6389 (2) | 0.48400 (13) | 0.0165 (4) | |
| H13 | −0.049035 | 0.684050 | 0.497503 | 0.020* | |
| C14 | 0.1242 (2) | 0.6717 (3) | 0.40001 (11) | 0.0135 (3) | |
| H14 | 0.053015 | 0.737965 | 0.355540 | 0.016* | |
| C15 | 0.3493 (2) | 0.64320 (19) | 0.28939 (12) | 0.0113 (3) | |
| C16 | 0.5780 (3) | 0.4348 (2) | 0.42876 (14) | 0.0190 (4) | |
| H16A | 0.563507 | 0.383911 | 0.367518 | 0.029* | |
| H16B | 0.615433 | 0.352757 | 0.476157 | 0.029* | |
| H16C | 0.671673 | 0.519549 | 0.431646 | 0.029* |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.00830 (8) | 0.01066 (9) | 0.01290 (9) | 0.00019 (8) | 0.00197 (6) | 0.00037 (9) |
| Cl1 | 0.01314 (19) | 0.0252 (2) | 0.01136 (19) | 0.00219 (17) | −0.00077 (14) | 0.00050 (17) |
| Cl2 | 0.0186 (2) | 0.01049 (19) | 0.0251 (2) | −0.00277 (17) | 0.00381 (18) | 0.00124 (18) |
| O1 | 0.0107 (6) | 0.0098 (6) | 0.0171 (6) | 0.0007 (5) | −0.0001 (5) | −0.0020 (5) |
| O2 | 0.0082 (5) | 0.0214 (6) | 0.0143 (5) | −0.0029 (6) | 0.0020 (4) | −0.0005 (6) |
| N1 | 0.0123 (7) | 0.0113 (7) | 0.0318 (10) | 0.0008 (6) | −0.0042 (7) | −0.0047 (7) |
| N2 | 0.0094 (6) | 0.0219 (9) | 0.0117 (7) | −0.0016 (6) | 0.0021 (5) | 0.0013 (6) |
| C1 | 0.0093 (7) | 0.0084 (7) | 0.0136 (8) | −0.0015 (6) | 0.0022 (6) | −0.0001 (6) |
| C2 | 0.0132 (7) | 0.0134 (8) | 0.0138 (7) | −0.0011 (7) | 0.0036 (6) | 0.0006 (8) |
| C3 | 0.0145 (8) | 0.0171 (8) | 0.0207 (9) | 0.0013 (7) | 0.0077 (7) | −0.0026 (8) |
| C4 | 0.0127 (8) | 0.0165 (8) | 0.0237 (10) | 0.0034 (7) | 0.0012 (7) | 0.0018 (8) |
| C5 | 0.0157 (8) | 0.0168 (9) | 0.0153 (8) | 0.0016 (8) | −0.0015 (6) | 0.0019 (8) |
| C6 | 0.0128 (8) | 0.0123 (7) | 0.0137 (8) | −0.0016 (6) | 0.0030 (6) | −0.0023 (6) |
| C7 | 0.0114 (8) | 0.0107 (8) | 0.0108 (8) | −0.0005 (6) | 0.0018 (6) | 0.0016 (6) |
| C8 | 0.0220 (9) | 0.0320 (13) | 0.0154 (9) | 0.0030 (8) | 0.0043 (7) | 0.0001 (8) |
| C9 | 0.0099 (7) | 0.0122 (7) | 0.0117 (8) | −0.0036 (6) | 0.0017 (6) | −0.0022 (7) |
| C10 | 0.0126 (8) | 0.0126 (7) | 0.0147 (8) | −0.0019 (6) | −0.0011 (6) | −0.0009 (7) |
| C11 | 0.0220 (10) | 0.0150 (8) | 0.0149 (9) | −0.0045 (7) | −0.0008 (7) | 0.0014 (7) |
| C12 | 0.0224 (10) | 0.0193 (9) | 0.0137 (9) | −0.0072 (7) | 0.0064 (7) | −0.0015 (7) |
| C13 | 0.0140 (8) | 0.0200 (9) | 0.0164 (8) | −0.0036 (6) | 0.0056 (6) | −0.0041 (7) |
| C14 | 0.0119 (7) | 0.0138 (7) | 0.0148 (7) | −0.0013 (8) | 0.0015 (5) | −0.0016 (8) |
| C15 | 0.0113 (7) | 0.0098 (8) | 0.0128 (8) | 0.0000 (5) | 0.0017 (6) | −0.0008 (6) |
| C16 | 0.0146 (8) | 0.0209 (9) | 0.0212 (10) | 0.0048 (7) | 0.0008 (7) | 0.0036 (8) |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Geometric parameters (Å, º)
| Zn1—Cl1 | 2.2340 (4) | C5—H5 | 0.9500 |
| Zn1—Cl2 | 2.1947 (5) | C5—C6 | 1.389 (2) |
| Zn1—O1 | 2.0169 (13) | C6—H6 | 0.9500 |
| Zn1—O2 | 1.9781 (11) | C8—H8A | 0.9800 |
| O1—C7 | 1.266 (2) | C8—H8B | 0.9800 |
| O2—C15 | 1.2637 (19) | C8—H8C | 0.9800 |
| N1—H1A | 0.82 (2) | C9—C10 | 1.405 (2) |
| N1—H1B | 0.858 (19) | C9—C14 | 1.402 (2) |
| N1—C7 | 1.310 (2) | C9—C15 | 1.486 (2) |
| N2—H2A | 0.847 (18) | C10—C11 | 1.393 (3) |
| N2—H2B | 0.836 (18) | C10—C16 | 1.519 (3) |
| N2—C15 | 1.313 (2) | C11—H11 | 0.9500 |
| C1—C2 | 1.406 (2) | C11—C12 | 1.384 (3) |
| C1—C6 | 1.394 (2) | C12—H12 | 0.9500 |
| C1—C7 | 1.490 (2) | C12—C13 | 1.389 (3) |
| C2—C3 | 1.391 (2) | C13—H13 | 0.9500 |
| C2—C8 | 1.512 (2) | C13—C14 | 1.390 (2) |
| C3—H3 | 0.9500 | C14—H14 | 0.9500 |
| C3—C4 | 1.386 (3) | C16—H16A | 0.9800 |
| C4—H4 | 0.9500 | C16—H16B | 0.9800 |
| C4—C5 | 1.389 (3) | C16—H16C | 0.9800 |
| Cl2—Zn1—Cl1 | 125.120 (19) | N1—C7—C1 | 118.01 (16) |
| O1—Zn1—Cl1 | 107.22 (4) | C2—C8—H8A | 109.5 |
| O1—Zn1—Cl2 | 102.18 (4) | C2—C8—H8B | 109.5 |
| O2—Zn1—Cl1 | 108.84 (3) | C2—C8—H8C | 109.5 |
| O2—Zn1—Cl2 | 107.52 (4) | H8A—C8—H8B | 109.5 |
| O2—Zn1—O1 | 103.91 (5) | H8A—C8—H8C | 109.5 |
| C7—O1—Zn1 | 130.95 (12) | H8B—C8—H8C | 109.5 |
| C15—O2—Zn1 | 131.79 (10) | C10—C9—C15 | 121.02 (15) |
| H1A—N1—H1B | 119 (2) | C14—C9—C10 | 120.54 (16) |
| C7—N1—H1A | 118.0 (15) | C14—C9—C15 | 118.44 (15) |
| C7—N1—H1B | 121.5 (16) | C9—C10—C16 | 123.15 (16) |
| H2A—N2—H2B | 118 (2) | C11—C10—C9 | 117.69 (17) |
| C15—N2—H2A | 119.8 (14) | C11—C10—C16 | 119.12 (16) |
| C15—N2—H2B | 121.5 (15) | C10—C11—H11 | 119.0 |
| C2—C1—C7 | 121.28 (15) | C12—C11—C10 | 122.04 (17) |
| C6—C1—C2 | 120.96 (16) | C12—C11—H11 | 119.0 |
| C6—C1—C7 | 117.75 (16) | C11—C12—H12 | 120.0 |
| C1—C2—C8 | 122.60 (16) | C11—C12—C13 | 119.91 (18) |
| C3—C2—C1 | 117.57 (15) | C13—C12—H12 | 120.0 |
| C3—C2—C8 | 119.84 (16) | C12—C13—H13 | 120.2 |
| C2—C3—H3 | 119.1 | C12—C13—C14 | 119.52 (18) |
| C4—C3—C2 | 121.86 (17) | C14—C13—H13 | 120.2 |
| C4—C3—H3 | 119.1 | C9—C14—H14 | 119.9 |
| C3—C4—H4 | 120.1 | C13—C14—C9 | 120.27 (16) |
| C3—C4—C5 | 119.86 (17) | C13—C14—H14 | 119.9 |
| C5—C4—H4 | 120.1 | O2—C15—N2 | 122.81 (16) |
| C4—C5—H5 | 120.2 | O2—C15—C9 | 119.34 (14) |
| C4—C5—C6 | 119.70 (16) | N2—C15—C9 | 117.86 (15) |
| C6—C5—H5 | 120.2 | C10—C16—H16A | 109.5 |
| C1—C6—H6 | 120.0 | C10—C16—H16B | 109.5 |
| C5—C6—C1 | 120.02 (16) | C10—C16—H16C | 109.5 |
| C5—C6—H6 | 120.0 | H16A—C16—H16B | 109.5 |
| O1—C7—N1 | 122.80 (17) | H16A—C16—H16C | 109.5 |
| O1—C7—C1 | 119.18 (15) | H16B—C16—H16C | 109.5 |
| Zn1—O1—C7—N1 | −6.3 (3) | C7—C1—C6—C5 | 177.87 (16) |
| Zn1—O1—C7—C1 | 174.92 (12) | C8—C2—C3—C4 | −179.24 (17) |
| Zn1—O2—C15—N2 | −11.9 (3) | C9—C10—C11—C12 | −2.2 (3) |
| Zn1—O2—C15—C9 | 168.30 (12) | C10—C9—C14—C13 | −0.1 (3) |
| C1—C2—C3—C4 | 0.9 (3) | C10—C9—C15—O2 | −38.3 (2) |
| C2—C1—C6—C5 | −1.9 (3) | C10—C9—C15—N2 | 141.92 (17) |
| C2—C1—C7—O1 | −119.46 (19) | C10—C11—C12—C13 | 1.1 (3) |
| C2—C1—C7—N1 | 61.7 (2) | C11—C12—C13—C14 | 0.6 (3) |
| C2—C3—C4—C5 | −0.7 (3) | C12—C13—C14—C9 | −1.1 (3) |
| C3—C4—C5—C6 | −0.8 (3) | C14—C9—C10—C11 | 1.7 (3) |
| C4—C5—C6—C1 | 2.1 (3) | C14—C9—C10—C16 | 179.43 (17) |
| C6—C1—C2—C3 | 0.5 (3) | C14—C9—C15—O2 | 142.68 (18) |
| C6—C1—C2—C8 | −179.44 (18) | C14—C9—C15—N2 | −37.1 (2) |
| C6—C1—C7—O1 | 60.7 (2) | C15—C9—C10—C11 | −177.30 (16) |
| C6—C1—C7—N1 | −118.08 (19) | C15—C9—C10—C16 | 0.4 (3) |
| C7—C1—C2—C3 | −179.36 (16) | C15—C9—C14—C13 | 178.94 (16) |
| C7—C1—C2—C8 | 0.7 (3) | C16—C10—C11—C12 | 179.92 (17) |
Dichloridobis(2-methylbenzamide-κO)zinc(II) (2) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···Cl2i | 0.82 (2) | 2.57 (2) | 3.2916 (17) | 147 (2) |
| N1—H1B···Cl1 | 0.86 (2) | 2.54 (2) | 3.3077 (17) | 150 (2) |
| N2—H2A···Cl1 | 0.85 (2) | 2.52 (2) | 3.2667 (16) | 148 (2) |
| N2—H2B···O1ii | 0.84 (2) | 2.14 (2) | 2.949 (2) | 163 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z.
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Crystal data
| [ZnCl2(C8H9NO)2] | F(000) = 832 |
| Mr = 406.59 | Dx = 1.519 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 13.9452 (11) Å | Cell parameters from 6211 reflections |
| b = 18.9742 (16) Å | θ = 3.1–28.7° |
| c = 7.0651 (6) Å | µ = 1.69 mm−1 |
| β = 108.021 (2)° | T = 100 K |
| V = 1777.7 (3) Å3 | Needle, clear light colourless |
| Z = 4 | 0.42 × 0.14 × 0.14 mm |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Data collection
| Bruker APEXII CCD diffractometer | 2295 independent reflections |
| Radiation source: sealed tube | 2023 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.027 |
| Detector resolution: 8 pixels mm-1 | θmax = 28.7°, θmin = 1.9° |
| ω and φ scans | h = −18→18 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −25→25 |
| Tmin = 0.620, Tmax = 0.746 | l = −9→9 |
| 12177 measured reflections |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.022 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0284P)2 + 1.5576P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.001 |
| 2295 reflections | Δρmax = 0.39 e Å−3 |
| 113 parameters | Δρmin = −0.26 e Å−3 |
| 17 restraints |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Special details
| 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. |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Zn1 | 0.500000 | 0.38624 (2) | 0.750000 | 0.01707 (8) | |
| Cl1 | 0.62434 (3) | 0.44400 (2) | 0.97242 (5) | 0.02080 (9) | |
| O1 | 0.56261 (8) | 0.31701 (5) | 0.61793 (15) | 0.0204 (2) | |
| N1 | 0.61233 (10) | 0.38460 (7) | 0.40319 (19) | 0.0202 (3) | |
| H1A | 0.5980 (15) | 0.4225 (9) | 0.452 (3) | 0.030* | |
| H1B | 0.6324 (15) | 0.3898 (10) | 0.302 (3) | 0.030* | |
| C1 | 0.62069 (10) | 0.25740 (7) | 0.3812 (2) | 0.0158 (3) | |
| C2 | 0.61038 (10) | 0.19345 (8) | 0.4691 (2) | 0.0180 (3) | |
| H2 | 0.588635 | 0.193263 | 0.583965 | 0.022* | |
| C3 | 0.63116 (12) | 0.12987 (8) | 0.3927 (2) | 0.0221 (3) | |
| C4 | 0.66207 (12) | 0.13155 (8) | 0.2221 (2) | 0.0247 (3) | |
| H4 | 0.676788 | 0.088681 | 0.167359 | 0.030* | |
| C5 | 0.67144 (12) | 0.19491 (8) | 0.1323 (2) | 0.0234 (3) | |
| H5 | 0.691823 | 0.195033 | 0.015859 | 0.028* | |
| C6 | 0.65141 (11) | 0.25802 (8) | 0.2104 (2) | 0.0187 (3) | |
| H6 | 0.658428 | 0.301380 | 0.148814 | 0.022* | |
| C7 | 0.59708 (10) | 0.32279 (7) | 0.4738 (2) | 0.0158 (3) | |
| C8 | 0.62193 (14) | 0.06111 (9) | 0.4921 (3) | 0.0332 (4) | |
| H8A | 0.630921 | 0.069427 | 0.633494 | 0.050* | 0.54 (2) |
| H8B | 0.673809 | 0.028337 | 0.478992 | 0.050* | 0.54 (2) |
| H8C | 0.555047 | 0.040823 | 0.428655 | 0.050* | 0.54 (2) |
| H8D | 0.608931 | 0.022964 | 0.393933 | 0.050* | 0.46 (2) |
| H8E | 0.566042 | 0.064055 | 0.548436 | 0.050* | 0.46 (2) |
| H8F | 0.684804 | 0.051568 | 0.598773 | 0.050* | 0.46 (2) |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.02315 (13) | 0.01516 (12) | 0.01467 (12) | 0.000 | 0.00842 (9) | 0.000 |
| Cl1 | 0.02732 (19) | 0.01659 (17) | 0.01841 (16) | −0.00333 (13) | 0.00694 (14) | −0.00035 (12) |
| O1 | 0.0265 (6) | 0.0175 (5) | 0.0197 (5) | 0.0021 (4) | 0.0110 (4) | −0.0008 (4) |
| N1 | 0.0259 (7) | 0.0152 (6) | 0.0214 (6) | 0.0015 (5) | 0.0099 (5) | −0.0002 (5) |
| C1 | 0.0121 (6) | 0.0173 (6) | 0.0165 (6) | 0.0004 (5) | 0.0023 (5) | −0.0016 (5) |
| C2 | 0.0148 (7) | 0.0199 (7) | 0.0184 (6) | 0.0015 (5) | 0.0038 (5) | 0.0002 (5) |
| C3 | 0.0189 (7) | 0.0171 (7) | 0.0283 (8) | 0.0006 (5) | 0.0046 (6) | 0.0001 (6) |
| C4 | 0.0234 (8) | 0.0204 (7) | 0.0306 (8) | 0.0008 (6) | 0.0089 (6) | −0.0079 (6) |
| C5 | 0.0216 (7) | 0.0277 (8) | 0.0233 (7) | −0.0005 (6) | 0.0103 (6) | −0.0057 (6) |
| C6 | 0.0170 (7) | 0.0196 (7) | 0.0196 (6) | −0.0007 (5) | 0.0058 (5) | −0.0006 (5) |
| C7 | 0.0130 (6) | 0.0168 (6) | 0.0157 (6) | 0.0004 (5) | 0.0015 (5) | −0.0008 (5) |
| C8 | 0.0398 (10) | 0.0178 (8) | 0.0439 (10) | 0.0011 (7) | 0.0156 (8) | 0.0039 (7) |
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Geometric parameters (Å, º)
| Zn1—Cl1 | 2.2341 (4) | C3—C4 | 1.400 (2) |
| Zn1—Cl1i | 2.2341 (4) | C3—C8 | 1.506 (2) |
| Zn1—O1i | 1.9652 (10) | C4—H4 | 0.9500 |
| Zn1—O1 | 1.9652 (10) | C4—C5 | 1.384 (2) |
| O1—C7 | 1.2581 (16) | C5—H5 | 0.9500 |
| N1—H1A | 0.847 (15) | C5—C6 | 1.383 (2) |
| N1—H1B | 0.848 (15) | C6—H6 | 0.9500 |
| N1—C7 | 1.3173 (18) | C8—H8A | 0.9800 |
| C1—C2 | 1.3906 (19) | C8—H8B | 0.9800 |
| C1—C6 | 1.3998 (19) | C8—H8C | 0.9800 |
| C1—C7 | 1.4863 (19) | C8—H8D | 0.9800 |
| C2—H2 | 0.9500 | C8—H8E | 0.9800 |
| C2—C3 | 1.388 (2) | C8—H8F | 0.9800 |
| Cl1—Zn1—Cl1i | 121.25 (2) | C5—C6—C1 | 119.36 (14) |
| O1i—Zn1—Cl1 | 110.86 (3) | C5—C6—H6 | 120.3 |
| O1—Zn1—Cl1i | 110.86 (3) | O1—C7—N1 | 122.08 (13) |
| O1—Zn1—Cl1 | 107.44 (3) | O1—C7—C1 | 118.40 (12) |
| O1i—Zn1—Cl1i | 107.44 (3) | N1—C7—C1 | 119.53 (12) |
| O1i—Zn1—O1 | 96.12 (6) | C3—C8—H8A | 109.5 |
| C7—O1—Zn1 | 131.54 (9) | C3—C8—H8B | 109.5 |
| H1A—N1—H1B | 114.8 (18) | C3—C8—H8C | 109.5 |
| C7—N1—H1A | 121.2 (13) | C3—C8—H8D | 109.5 |
| C7—N1—H1B | 123.8 (13) | C3—C8—H8E | 109.5 |
| C2—C1—C6 | 119.59 (13) | C3—C8—H8F | 109.5 |
| C2—C1—C7 | 117.67 (12) | H8A—C8—H8B | 109.5 |
| C6—C1—C7 | 122.74 (13) | H8A—C8—H8C | 109.5 |
| C1—C2—H2 | 119.3 | H8A—C8—H8D | 141.1 |
| C3—C2—C1 | 121.45 (13) | H8A—C8—H8E | 56.3 |
| C3—C2—H2 | 119.3 | H8A—C8—H8F | 56.3 |
| C2—C3—C4 | 118.15 (14) | H8B—C8—H8C | 109.5 |
| C2—C3—C8 | 120.88 (15) | H8B—C8—H8D | 56.3 |
| C4—C3—C8 | 120.97 (14) | H8B—C8—H8E | 141.1 |
| C3—C4—H4 | 119.6 | H8B—C8—H8F | 56.3 |
| C5—C4—C3 | 120.80 (14) | H8C—C8—H8D | 56.3 |
| C5—C4—H4 | 119.6 | H8C—C8—H8E | 56.3 |
| C4—C5—H5 | 119.7 | H8C—C8—H8F | 141.1 |
| C6—C5—C4 | 120.65 (14) | H8D—C8—H8E | 109.5 |
| C6—C5—H5 | 119.7 | H8D—C8—H8F | 109.5 |
| C1—C6—H6 | 120.3 | H8E—C8—H8F | 109.5 |
| Zn1—O1—C7—N1 | 12.2 (2) | C3—C4—C5—C6 | 0.7 (2) |
| Zn1—O1—C7—C1 | −167.56 (9) | C4—C5—C6—C1 | −0.5 (2) |
| C1—C2—C3—C4 | −0.7 (2) | C6—C1—C2—C3 | 0.8 (2) |
| C1—C2—C3—C8 | 178.60 (15) | C6—C1—C7—O1 | 174.61 (13) |
| C2—C1—C6—C5 | −0.3 (2) | C6—C1—C7—N1 | −5.2 (2) |
| C2—C1—C7—O1 | −4.73 (19) | C7—C1—C2—C3 | −179.79 (13) |
| C2—C1—C7—N1 | 175.49 (13) | C7—C1—C6—C5 | −179.60 (13) |
| C2—C3—C4—C5 | −0.1 (2) | C8—C3—C4—C5 | −179.35 (15) |
Symmetry code: (i) −x+1, y, −z+3/2.
Dichloridobis(3-methylbenzamide-κO)zinc(II) (3) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···Cl1ii | 0.85 (2) | 2.56 (2) | 3.2854 (13) | 145 (2) |
| N1—H1B···Cl1iii | 0.85 (2) | 2.52 (2) | 3.2979 (13) | 153 (2) |
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, y, z−1.
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Crystal data
| [ZnCl2(C8H9NO)2] | F(000) = 832 |
| Mr = 406.59 | Dx = 1.537 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.8376 (4) Å | Cell parameters from 8511 reflections |
| b = 17.2694 (9) Å | θ = 2.4–30.1° |
| c = 14.9856 (7) Å | µ = 1.71 mm−1 |
| β = 96.893 (2)° | T = 100 K |
| V = 1756.73 (16) Å3 | Needle, clear light colourless |
| Z = 4 | 0.56 × 0.18 × 0.09 mm |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Data collection
| Bruker APEXII CCD diffractometer | 5376 independent reflections |
| Radiation source: sealed tube | 4283 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.051 |
| Detector resolution: 8 pixels mm-1 | θmax = 30.5°, θmin = 1.8° |
| ω and φ scans | h = −9→9 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −24→24 |
| Tmin = 0.629, Tmax = 0.746 | l = −21→21 |
| 33806 measured reflections |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.028P)2 + 0.9244P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 5376 reflections | Δρmax = 0.46 e Å−3 |
| 222 parameters | Δρmin = −0.32 e Å−3 |
| 4 restraints |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Special details
| 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. |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.62040 (3) | 0.33576 (2) | 0.90851 (2) | 0.01257 (6) | |
| Cl1 | 0.77285 (6) | 0.44248 (3) | 0.96142 (3) | 0.01698 (9) | |
| Cl2 | 0.47211 (6) | 0.26784 (3) | 1.00645 (3) | 0.01897 (9) | |
| O1 | 0.80611 (18) | 0.27132 (8) | 0.85157 (8) | 0.0185 (3) | |
| O2 | 0.42159 (16) | 0.36421 (7) | 0.80292 (7) | 0.0138 (2) | |
| N1 | 0.6780 (2) | 0.27321 (10) | 0.70593 (9) | 0.0173 (3) | |
| H1A | 0.581 (3) | 0.3025 (12) | 0.7182 (14) | 0.026* | |
| H1B | 0.679 (3) | 0.2600 (13) | 0.6506 (11) | 0.026* | |
| N2 | 0.1956 (2) | 0.41980 (11) | 0.87969 (10) | 0.0227 (4) | |
| H2A | 0.076 (3) | 0.4331 (14) | 0.8844 (16) | 0.034* | |
| H2B | 0.275 (3) | 0.4161 (14) | 0.9295 (12) | 0.034* | |
| C1 | 0.9836 (2) | 0.20466 (10) | 0.75021 (10) | 0.0121 (3) | |
| C2 | 1.1478 (2) | 0.20012 (10) | 0.81520 (10) | 0.0135 (3) | |
| H2 | 1.145841 | 0.225037 | 0.871603 | 0.016* | |
| C3 | 1.3132 (2) | 0.15949 (10) | 0.79764 (11) | 0.0147 (3) | |
| H3 | 1.424273 | 0.157277 | 0.842184 | 0.018* | |
| C4 | 1.3201 (2) | 0.12177 (10) | 0.71601 (11) | 0.0140 (3) | |
| C5 | 1.1545 (2) | 0.12644 (10) | 0.65131 (11) | 0.0149 (3) | |
| H5 | 1.156387 | 0.101115 | 0.595143 | 0.018* | |
| C6 | 0.9882 (2) | 0.16732 (10) | 0.66776 (10) | 0.0138 (3) | |
| H6 | 0.877513 | 0.169957 | 0.623050 | 0.017* | |
| C7 | 0.8142 (2) | 0.25188 (10) | 0.77107 (10) | 0.0130 (3) | |
| C8 | 1.4980 (3) | 0.07558 (11) | 0.69831 (12) | 0.0200 (4) | |
| H8A | 1.469032 | 0.020189 | 0.702178 | 0.030* | |
| H8B | 1.609350 | 0.088824 | 0.743154 | 0.030* | |
| H8C | 1.531608 | 0.087642 | 0.638088 | 0.030* | |
| C9 | 0.1206 (2) | 0.40383 (10) | 0.71921 (10) | 0.0135 (3) | |
| C10 | 0.1505 (2) | 0.35807 (11) | 0.64562 (11) | 0.0153 (3) | |
| H10 | 0.255602 | 0.321747 | 0.650256 | 0.018* | |
| C11 | 0.0270 (3) | 0.36541 (11) | 0.56531 (11) | 0.0189 (4) | |
| H11 | 0.047805 | 0.333358 | 0.515810 | 0.023* | |
| C12 | −0.1263 (3) | 0.41870 (11) | 0.55606 (12) | 0.0197 (4) | |
| C13 | −0.1537 (3) | 0.46467 (12) | 0.62984 (13) | 0.0250 (4) | |
| H13 | −0.257293 | 0.501643 | 0.624800 | 0.030* | |
| C14 | −0.0324 (3) | 0.45754 (11) | 0.71067 (12) | 0.0217 (4) | |
| H14 | −0.053924 | 0.489388 | 0.760262 | 0.026* | |
| C15 | 0.2540 (2) | 0.39488 (10) | 0.80440 (10) | 0.0131 (3) | |
| C16 | −0.2596 (3) | 0.42661 (13) | 0.46859 (13) | 0.0276 (4) | |
| H16A | −0.220031 | 0.389179 | 0.424975 | 0.041* | |
| H16B | −0.249033 | 0.479199 | 0.445066 | 0.041* | |
| H16C | −0.396095 | 0.416577 | 0.478950 | 0.041* |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.01264 (9) | 0.01536 (11) | 0.00929 (8) | 0.00095 (8) | −0.00036 (6) | −0.00125 (7) |
| Cl1 | 0.01717 (18) | 0.0165 (2) | 0.01668 (18) | −0.00171 (16) | −0.00044 (14) | −0.00253 (15) |
| Cl2 | 0.01998 (19) | 0.0250 (2) | 0.01107 (16) | −0.00528 (17) | −0.00144 (14) | 0.00284 (16) |
| O1 | 0.0177 (6) | 0.0255 (7) | 0.0120 (5) | 0.0070 (5) | 0.0000 (4) | −0.0039 (5) |
| O2 | 0.0119 (5) | 0.0180 (6) | 0.0111 (5) | 0.0022 (5) | −0.0002 (4) | −0.0012 (4) |
| N1 | 0.0164 (7) | 0.0238 (9) | 0.0112 (6) | 0.0065 (6) | −0.0008 (5) | −0.0040 (6) |
| N2 | 0.0158 (7) | 0.0376 (10) | 0.0141 (7) | 0.0066 (7) | −0.0002 (6) | −0.0059 (7) |
| C1 | 0.0123 (7) | 0.0114 (8) | 0.0123 (7) | −0.0012 (6) | 0.0009 (6) | 0.0002 (6) |
| C2 | 0.0147 (7) | 0.0146 (9) | 0.0107 (7) | −0.0008 (6) | −0.0006 (6) | −0.0007 (6) |
| C3 | 0.0133 (7) | 0.0152 (9) | 0.0146 (7) | −0.0004 (6) | −0.0024 (6) | 0.0012 (6) |
| C4 | 0.0129 (7) | 0.0117 (8) | 0.0177 (7) | −0.0005 (6) | 0.0029 (6) | 0.0010 (6) |
| C5 | 0.0173 (8) | 0.0140 (9) | 0.0133 (7) | −0.0001 (7) | 0.0018 (6) | −0.0023 (6) |
| C6 | 0.0141 (7) | 0.0144 (8) | 0.0125 (6) | −0.0001 (6) | −0.0003 (6) | −0.0011 (6) |
| C7 | 0.0128 (7) | 0.0134 (8) | 0.0126 (7) | −0.0022 (6) | 0.0006 (6) | −0.0007 (6) |
| C8 | 0.0151 (8) | 0.0196 (10) | 0.0250 (8) | 0.0023 (7) | 0.0012 (7) | −0.0032 (7) |
| C9 | 0.0127 (7) | 0.0132 (8) | 0.0139 (7) | −0.0006 (6) | −0.0015 (6) | −0.0014 (6) |
| C10 | 0.0147 (7) | 0.0167 (9) | 0.0140 (7) | 0.0023 (6) | 0.0001 (6) | −0.0011 (6) |
| C11 | 0.0214 (8) | 0.0213 (10) | 0.0134 (7) | −0.0010 (7) | −0.0010 (6) | −0.0039 (7) |
| C12 | 0.0194 (8) | 0.0182 (10) | 0.0193 (8) | −0.0021 (7) | −0.0065 (7) | 0.0020 (7) |
| C13 | 0.0219 (9) | 0.0201 (10) | 0.0301 (10) | 0.0084 (8) | −0.0088 (8) | −0.0032 (8) |
| C14 | 0.0221 (9) | 0.0195 (10) | 0.0218 (8) | 0.0060 (7) | −0.0040 (7) | −0.0064 (7) |
| C15 | 0.0132 (7) | 0.0130 (8) | 0.0128 (7) | −0.0016 (6) | 0.0001 (6) | −0.0014 (6) |
| C16 | 0.0282 (10) | 0.0273 (11) | 0.0237 (9) | −0.0014 (8) | −0.0121 (8) | 0.0023 (8) |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Geometric parameters (Å, º)
| Zn1—Cl1 | 2.2166 (5) | C5—H5 | 0.9500 |
| Zn1—Cl2 | 2.2170 (5) | C5—C6 | 1.385 (2) |
| Zn1—O1 | 1.9592 (12) | C6—H6 | 0.9500 |
| Zn1—O2 | 2.0191 (11) | C8—H8A | 0.9800 |
| O1—C7 | 1.2599 (19) | C8—H8B | 0.9800 |
| O2—C15 | 1.265 (2) | C8—H8C | 0.9800 |
| N1—H1A | 0.869 (16) | C9—C10 | 1.392 (2) |
| N1—H1B | 0.861 (15) | C9—C14 | 1.393 (2) |
| N1—C7 | 1.318 (2) | C9—C15 | 1.485 (2) |
| N2—H2A | 0.858 (16) | C10—H10 | 0.9500 |
| N2—H2B | 0.871 (16) | C10—C11 | 1.391 (2) |
| N2—C15 | 1.313 (2) | C11—H11 | 0.9500 |
| C1—C2 | 1.398 (2) | C11—C12 | 1.389 (3) |
| C1—C6 | 1.397 (2) | C12—C13 | 1.392 (3) |
| C1—C7 | 1.480 (2) | C12—C16 | 1.510 (2) |
| C2—H2 | 0.9500 | C13—H13 | 0.9500 |
| C2—C3 | 1.382 (2) | C13—C14 | 1.389 (2) |
| C3—H3 | 0.9500 | C14—H14 | 0.9500 |
| C3—C4 | 1.392 (2) | C16—H16A | 0.9800 |
| C4—C5 | 1.402 (2) | C16—H16B | 0.9800 |
| C4—C8 | 1.505 (2) | C16—H16C | 0.9800 |
| Cl1—Zn1—Cl2 | 115.836 (17) | N1—C7—C1 | 119.92 (14) |
| O1—Zn1—Cl1 | 109.06 (4) | C4—C8—H8A | 109.5 |
| O1—Zn1—Cl2 | 111.08 (4) | C4—C8—H8B | 109.5 |
| O1—Zn1—O2 | 101.98 (5) | C4—C8—H8C | 109.5 |
| O2—Zn1—Cl1 | 108.75 (4) | H8A—C8—H8B | 109.5 |
| O2—Zn1—Cl2 | 109.22 (4) | H8A—C8—H8C | 109.5 |
| C7—O1—Zn1 | 132.35 (11) | H8B—C8—H8C | 109.5 |
| C15—O2—Zn1 | 127.89 (10) | C10—C9—C14 | 119.06 (15) |
| H1A—N1—H1B | 117 (2) | C10—C9—C15 | 119.24 (15) |
| C7—N1—H1A | 119.6 (15) | C14—C9—C15 | 121.69 (15) |
| C7—N1—H1B | 123.4 (15) | C9—C10—H10 | 119.9 |
| H2A—N2—H2B | 117 (2) | C11—C10—C9 | 120.14 (16) |
| C15—N2—H2A | 123.2 (16) | C11—C10—H10 | 119.9 |
| C15—N2—H2B | 119.3 (16) | C10—C11—H11 | 119.4 |
| C2—C1—C7 | 117.86 (14) | C12—C11—C10 | 121.30 (16) |
| C6—C1—C2 | 119.24 (15) | C12—C11—H11 | 119.4 |
| C6—C1—C7 | 122.85 (14) | C11—C12—C13 | 118.05 (15) |
| C1—C2—H2 | 119.9 | C11—C12—C16 | 121.06 (17) |
| C3—C2—C1 | 120.19 (15) | C13—C12—C16 | 120.89 (17) |
| C3—C2—H2 | 119.9 | C12—C13—H13 | 119.4 |
| C2—C3—H3 | 119.3 | C14—C13—C12 | 121.28 (17) |
| C2—C3—C4 | 121.31 (14) | C14—C13—H13 | 119.4 |
| C4—C3—H3 | 119.3 | C9—C14—H14 | 119.9 |
| C3—C4—C5 | 118.12 (15) | C13—C14—C9 | 120.16 (17) |
| C3—C4—C8 | 121.10 (14) | C13—C14—H14 | 119.9 |
| C5—C4—C8 | 120.77 (15) | O2—C15—N2 | 121.42 (14) |
| C4—C5—H5 | 119.4 | O2—C15—C9 | 119.51 (14) |
| C6—C5—C4 | 121.21 (15) | N2—C15—C9 | 119.07 (15) |
| C6—C5—H5 | 119.4 | C12—C16—H16A | 109.5 |
| C1—C6—H6 | 120.0 | C12—C16—H16B | 109.5 |
| C5—C6—C1 | 119.92 (14) | C12—C16—H16C | 109.5 |
| C5—C6—H6 | 120.0 | H16A—C16—H16B | 109.5 |
| O1—C7—N1 | 121.75 (16) | H16A—C16—H16C | 109.5 |
| O1—C7—C1 | 118.33 (14) | H16B—C16—H16C | 109.5 |
| Zn1—O1—C7—N1 | −2.3 (3) | C7—C1—C6—C5 | 177.51 (16) |
| Zn1—O1—C7—C1 | 176.97 (12) | C8—C4—C5—C6 | 178.48 (17) |
| Zn1—O2—C15—N2 | 7.0 (3) | C9—C10—C11—C12 | 0.8 (3) |
| Zn1—O2—C15—C9 | −173.68 (11) | C10—C9—C14—C13 | 0.4 (3) |
| C1—C2—C3—C4 | −0.6 (3) | C10—C9—C15—O2 | 20.4 (2) |
| C2—C1—C6—C5 | 0.0 (3) | C10—C9—C15—N2 | −160.32 (18) |
| C2—C1—C7—O1 | −15.5 (2) | C10—C11—C12—C13 | −0.2 (3) |
| C2—C1—C7—N1 | 163.79 (17) | C10—C11—C12—C16 | 179.77 (18) |
| C2—C3—C4—C5 | 0.4 (3) | C11—C12—C13—C14 | −0.3 (3) |
| C2—C3—C4—C8 | −178.10 (16) | C12—C13—C14—C9 | 0.2 (3) |
| C3—C4—C5—C6 | 0.0 (3) | C14—C9—C10—C11 | −0.9 (3) |
| C4—C5—C6—C1 | −0.2 (3) | C14—C9—C15—O2 | −158.86 (17) |
| C6—C1—C2—C3 | 0.4 (3) | C14—C9—C15—N2 | 20.5 (3) |
| C6—C1—C7—O1 | 166.97 (16) | C15—C9—C10—C11 | 179.83 (16) |
| C6—C1—C7—N1 | −13.8 (3) | C15—C9—C14—C13 | 179.64 (18) |
| C7—C1—C2—C3 | −177.27 (16) | C16—C12—C13—C14 | 179.70 (19) |
Dichloridobis(4-methylbenzamide-κO)zinc(II) (4) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2 | 0.87 (2) | 2.07 (2) | 2.8753 (19) | 154 (2) |
| N1—H1B···Cl2i | 0.86 (2) | 2.49 (2) | 3.2265 (14) | 145 (2) |
| N2—H2A···Cl1ii | 0.86 (2) | 2.50 (2) | 3.2956 (16) | 155 (2) |
| N2—H2B···Cl2 | 0.87 (2) | 3.05 (2) | 3.6341 (17) | 126 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, y, z.
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Crystal data
| [ZnCl2(C7H7NO2)2] | F(000) = 832 |
| Mr = 410.54 | Dx = 1.696 Mg m−3 |
| Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.0532 (6) Å | Cell parameters from 5843 reflections |
| b = 21.3776 (17) Å | θ = 2.7–27.6° |
| c = 11.1181 (9) Å | µ = 1.88 mm−1 |
| β = 106.477 (2)° | T = 100 K |
| V = 1607.5 (2) Å3 | Block, clear light colourless |
| Z = 4 | 0.15 × 0.09 × 0.07 mm |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Data collection
| Bruker APEXII CCD diffractometer | 4168 independent reflections |
| Radiation source: sealed tube | 3809 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.042 |
| Detector resolution: 8 pixels mm-1 | θmax = 28.7°, θmin = 1.9° |
| ω and φ scans | h = −9→9 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −28→28 |
| Tmin = 0.673, Tmax = 0.746 | l = −15→15 |
| 17255 measured reflections |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Refinement
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.023P)2 + 0.9687P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.065 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.46 e Å−3 |
| 4168 reflections | Δρmin = −0.29 e Å−3 |
| 227 parameters | Absolute structure: Refined as an inversion twin |
| 8 restraints | Absolute structure parameter: 0.024 (13) |
| Primary atom site location: dual |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Special details
| 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. |
| Refinement. Refined as a 2-component inversion twin. |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.53881 (5) | 0.85209 (2) | 0.23775 (4) | 0.01454 (12) | |
| Cl1 | 0.73319 (15) | 0.92222 (5) | 0.18199 (9) | 0.0198 (2) | |
| Cl2 | 0.21825 (15) | 0.86831 (5) | 0.14477 (10) | 0.0210 (2) | |
| O1 | 0.5952 (4) | 0.84920 (13) | 0.4225 (3) | 0.0171 (6) | |
| O2 | 0.6040 (5) | 0.76660 (13) | 0.2016 (3) | 0.0202 (6) | |
| O3 | 0.7811 (5) | 0.80301 (14) | 1.0011 (3) | 0.0203 (7) | |
| H3 | 0.833 (7) | 0.828 (2) | 1.059 (4) | 0.030* | |
| O4 | 0.6608 (5) | 0.49561 (14) | −0.0004 (3) | 0.0260 (7) | |
| H4 | 0.681 (8) | 0.4641 (19) | 0.041 (5) | 0.039* | |
| N1 | 0.6218 (6) | 0.95087 (17) | 0.4782 (3) | 0.0188 (8) | |
| H1A | 0.606 (7) | 0.960 (2) | 0.401 (3) | 0.028* | |
| H1B | 0.644 (7) | 0.9847 (17) | 0.524 (4) | 0.028* | |
| N2 | 0.7170 (6) | 0.72093 (18) | 0.3908 (3) | 0.0203 (8) | |
| H2A | 0.711 (8) | 0.7563 (16) | 0.422 (5) | 0.030* | |
| H2B | 0.757 (8) | 0.6873 (17) | 0.428 (4) | 0.030* | |
| C1 | 0.6588 (6) | 0.87096 (18) | 0.6380 (4) | 0.0129 (8) | |
| C2 | 0.7355 (6) | 0.91117 (19) | 0.7389 (4) | 0.0154 (8) | |
| H2 | 0.759638 | 0.953737 | 0.723612 | 0.018* | |
| C3 | 0.7767 (6) | 0.88968 (19) | 0.8609 (4) | 0.0153 (8) | |
| H3A | 0.829009 | 0.917405 | 0.929006 | 0.018* | |
| C4 | 0.7414 (6) | 0.8275 (2) | 0.8836 (4) | 0.0153 (8) | |
| C5 | 0.6645 (6) | 0.78625 (19) | 0.7834 (4) | 0.0157 (8) | |
| H5 | 0.641179 | 0.743710 | 0.799426 | 0.019* | |
| C6 | 0.6234 (6) | 0.80752 (19) | 0.6626 (4) | 0.0156 (8) | |
| H6 | 0.570865 | 0.779649 | 0.594761 | 0.019* | |
| C7 | 0.6229 (6) | 0.89057 (18) | 0.5072 (4) | 0.0135 (8) | |
| C8 | 0.6692 (6) | 0.65874 (18) | 0.2021 (4) | 0.0129 (8) | |
| C9 | 0.7129 (6) | 0.60210 (19) | 0.2654 (4) | 0.0153 (8) | |
| H9 | 0.745040 | 0.601421 | 0.354333 | 0.018* | |
| C10 | 0.7104 (6) | 0.54637 (19) | 0.2002 (4) | 0.0169 (8) | |
| H10 | 0.738364 | 0.507780 | 0.244024 | 0.020* | |
| C11 | 0.6661 (6) | 0.5479 (2) | 0.0692 (4) | 0.0165 (8) | |
| C12 | 0.6224 (6) | 0.6047 (2) | 0.0046 (4) | 0.0178 (9) | |
| H12 | 0.592215 | 0.605752 | −0.084269 | 0.021* | |
| C13 | 0.6238 (6) | 0.65941 (19) | 0.0717 (4) | 0.0154 (8) | |
| H13 | 0.593257 | 0.697989 | 0.028103 | 0.018* | |
| C14 | 0.6644 (6) | 0.71888 (18) | 0.2678 (4) | 0.0137 (8) |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.0211 (2) | 0.0112 (2) | 0.01033 (19) | 0.0013 (2) | 0.00287 (15) | −0.0002 (2) |
| Cl1 | 0.0282 (5) | 0.0143 (5) | 0.0176 (5) | −0.0022 (4) | 0.0078 (4) | 0.0003 (4) |
| Cl2 | 0.0213 (5) | 0.0154 (5) | 0.0225 (5) | 0.0004 (4) | 0.0003 (4) | 0.0000 (4) |
| O1 | 0.0246 (15) | 0.0157 (15) | 0.0100 (14) | 0.0000 (12) | 0.0035 (11) | −0.0003 (11) |
| O2 | 0.0332 (17) | 0.0102 (15) | 0.0194 (15) | 0.0024 (12) | 0.0109 (13) | 0.0015 (11) |
| O3 | 0.0308 (17) | 0.0190 (16) | 0.0090 (14) | −0.0028 (13) | 0.0022 (12) | 0.0018 (11) |
| O4 | 0.0412 (19) | 0.0116 (16) | 0.0236 (17) | 0.0012 (14) | 0.0068 (15) | −0.0021 (12) |
| N1 | 0.031 (2) | 0.0137 (19) | 0.0106 (17) | 0.0004 (16) | 0.0046 (15) | 0.0008 (13) |
| N2 | 0.032 (2) | 0.0143 (19) | 0.0137 (18) | 0.0036 (17) | 0.0043 (16) | −0.0014 (14) |
| C1 | 0.014 (2) | 0.0111 (18) | 0.0125 (18) | 0.0009 (15) | 0.0028 (15) | −0.0019 (15) |
| C2 | 0.018 (2) | 0.012 (2) | 0.017 (2) | 0.0015 (15) | 0.0071 (16) | −0.0013 (15) |
| C3 | 0.020 (2) | 0.014 (2) | 0.0111 (19) | 0.0004 (16) | 0.0025 (15) | −0.0033 (14) |
| C4 | 0.014 (2) | 0.022 (2) | 0.0099 (18) | 0.0026 (16) | 0.0039 (15) | 0.0029 (15) |
| C5 | 0.018 (2) | 0.013 (2) | 0.016 (2) | −0.0004 (16) | 0.0062 (15) | 0.0012 (15) |
| C6 | 0.0155 (19) | 0.015 (2) | 0.016 (2) | −0.0007 (16) | 0.0039 (16) | −0.0026 (16) |
| C7 | 0.0138 (19) | 0.014 (2) | 0.0132 (19) | −0.0013 (15) | 0.0052 (15) | −0.0012 (15) |
| C8 | 0.0136 (18) | 0.0098 (19) | 0.0148 (19) | −0.0006 (14) | 0.0035 (15) | 0.0002 (14) |
| C9 | 0.018 (2) | 0.012 (2) | 0.0148 (19) | −0.0005 (16) | 0.0037 (16) | 0.0013 (15) |
| C10 | 0.021 (2) | 0.0115 (19) | 0.018 (2) | 0.0009 (16) | 0.0044 (16) | 0.0023 (15) |
| C11 | 0.019 (2) | 0.014 (2) | 0.017 (2) | −0.0016 (16) | 0.0038 (16) | −0.0024 (15) |
| C12 | 0.020 (2) | 0.021 (2) | 0.0118 (19) | −0.0001 (17) | 0.0022 (16) | −0.0021 (16) |
| C13 | 0.0163 (19) | 0.013 (2) | 0.016 (2) | −0.0018 (15) | 0.0033 (15) | 0.0020 (15) |
| C14 | 0.0148 (18) | 0.0110 (19) | 0.016 (2) | −0.0023 (15) | 0.0061 (15) | 0.0014 (15) |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Geometric parameters (Å, º)
| Zn1—Cl1 | 2.2347 (11) | C2—H2 | 0.9500 |
| Zn1—Cl2 | 2.2305 (11) | C2—C3 | 1.383 (6) |
| Zn1—O1 | 1.980 (3) | C3—H3A | 0.9500 |
| Zn1—O2 | 1.954 (3) | C3—C4 | 1.388 (6) |
| O1—C7 | 1.266 (5) | C4—C5 | 1.404 (5) |
| O2—C14 | 1.259 (5) | C5—H5 | 0.9500 |
| O3—H3 | 0.84 (3) | C5—C6 | 1.369 (6) |
| O3—C4 | 1.361 (5) | C6—H6 | 0.9500 |
| O4—H4 | 0.80 (3) | C8—C9 | 1.390 (5) |
| O4—C11 | 1.353 (5) | C8—C13 | 1.394 (6) |
| N1—H1A | 0.86 (3) | C8—C14 | 1.483 (5) |
| N1—H1B | 0.87 (3) | C9—H9 | 0.9500 |
| N1—C7 | 1.328 (5) | C9—C10 | 1.392 (6) |
| N2—H2A | 0.84 (3) | C10—H10 | 0.9500 |
| N2—H2B | 0.84 (3) | C10—C11 | 1.400 (6) |
| N2—C14 | 1.313 (5) | C11—C12 | 1.401 (6) |
| C1—C2 | 1.395 (5) | C12—H12 | 0.9500 |
| C1—C6 | 1.419 (5) | C12—C13 | 1.386 (6) |
| C1—C7 | 1.465 (5) | C13—H13 | 0.9500 |
| Cl2—Zn1—Cl1 | 112.84 (4) | C6—C5—C4 | 119.8 (4) |
| O1—Zn1—Cl1 | 110.51 (9) | C6—C5—H5 | 120.1 |
| O1—Zn1—Cl2 | 111.39 (9) | C1—C6—H6 | 119.8 |
| O2—Zn1—Cl1 | 111.83 (10) | C5—C6—C1 | 120.4 (4) |
| O2—Zn1—Cl2 | 108.48 (10) | C5—C6—H6 | 119.8 |
| O2—Zn1—O1 | 101.21 (12) | O1—C7—N1 | 120.6 (4) |
| C7—O1—Zn1 | 133.9 (3) | O1—C7—C1 | 119.0 (4) |
| C14—O2—Zn1 | 134.3 (3) | N1—C7—C1 | 120.4 (4) |
| C4—O3—H3 | 115 (4) | C9—C8—C13 | 119.2 (4) |
| C11—O4—H4 | 113 (4) | C9—C8—C14 | 122.6 (4) |
| H1A—N1—H1B | 111 (5) | C13—C8—C14 | 118.2 (4) |
| C7—N1—H1A | 117 (3) | C8—C9—H9 | 119.5 |
| C7—N1—H1B | 132 (3) | C8—C9—C10 | 120.9 (4) |
| H2A—N2—H2B | 128 (5) | C10—C9—H9 | 119.5 |
| C14—N2—H2A | 116 (4) | C9—C10—H10 | 120.4 |
| C14—N2—H2B | 116 (4) | C9—C10—C11 | 119.2 (4) |
| C2—C1—C6 | 118.9 (4) | C11—C10—H10 | 120.4 |
| C2—C1—C7 | 122.7 (4) | O4—C11—C10 | 122.5 (4) |
| C6—C1—C7 | 118.3 (3) | O4—C11—C12 | 117.2 (4) |
| C1—C2—H2 | 119.7 | C10—C11—C12 | 120.3 (4) |
| C3—C2—C1 | 120.6 (4) | C11—C12—H12 | 120.4 |
| C3—C2—H2 | 119.7 | C13—C12—C11 | 119.3 (4) |
| C2—C3—H3A | 120.1 | C13—C12—H12 | 120.4 |
| C2—C3—C4 | 119.9 (4) | C8—C13—H13 | 119.5 |
| C4—C3—H3A | 120.1 | C12—C13—C8 | 121.1 (4) |
| O3—C4—C3 | 123.0 (4) | C12—C13—H13 | 119.5 |
| O3—C4—C5 | 116.6 (4) | O2—C14—N2 | 122.0 (4) |
| C3—C4—C5 | 120.4 (4) | O2—C14—C8 | 117.8 (3) |
| C4—C5—H5 | 120.1 | N2—C14—C8 | 120.2 (4) |
| Zn1—O1—C7—N1 | −1.8 (6) | C6—C1—C7—N1 | 168.7 (4) |
| Zn1—O1—C7—C1 | 179.0 (3) | C7—C1—C2—C3 | −176.6 (4) |
| Zn1—O2—C14—N2 | −7.0 (6) | C7—C1—C6—C5 | 176.6 (4) |
| Zn1—O2—C14—C8 | 171.2 (3) | C8—C9—C10—C11 | 1.0 (6) |
| O3—C4—C5—C6 | −179.2 (4) | C9—C8—C13—C12 | −0.2 (6) |
| O4—C11—C12—C13 | 179.3 (4) | C9—C8—C14—O2 | −173.0 (4) |
| C1—C2—C3—C4 | −0.1 (6) | C9—C8—C14—N2 | 5.2 (6) |
| C2—C1—C6—C5 | −0.2 (6) | C9—C10—C11—O4 | −180.0 (4) |
| C2—C1—C7—O1 | 164.6 (4) | C9—C10—C11—C12 | −0.8 (6) |
| C2—C1—C7—N1 | −14.6 (6) | C10—C11—C12—C13 | 0.1 (6) |
| C2—C3—C4—O3 | 179.0 (4) | C11—C12—C13—C8 | 0.5 (6) |
| C2—C3—C4—C5 | 0.2 (6) | C13—C8—C9—C10 | −0.5 (6) |
| C3—C4—C5—C6 | −0.3 (6) | C13—C8—C14—O2 | 5.6 (6) |
| C4—C5—C6—C1 | 0.3 (6) | C13—C8—C14—N2 | −176.1 (4) |
| C6—C1—C2—C3 | 0.1 (6) | C14—C8—C9—C10 | 178.1 (4) |
| C6—C1—C7—O1 | −12.0 (6) | C14—C8—C13—C12 | −179.0 (4) |
Dichloridobis(4-hydroxybenzamide-κO)zinc(II) (5) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···Cl1i | 0.84 (3) | 2.64 (4) | 3.322 (3) | 140 (5) |
| O3—H3···Cl2ii | 0.84 (3) | 2.75 (4) | 3.349 (3) | 130 (4) |
| O4—H4···Cl2iii | 0.80 (3) | 2.33 (3) | 3.131 (3) | 175 (6) |
| N1—H1A···Cl1 | 0.86 (3) | 2.93 (4) | 3.648 (4) | 142 (4) |
| N1—H1B···Cl1iv | 0.87 (3) | 2.61 (3) | 3.479 (4) | 173 (4) |
| N2—H2A···O1 | 0.84 (3) | 2.15 (3) | 2.924 (5) | 154 (5) |
| N2—H2B···Cl2v | 0.84 (3) | 2.77 (4) | 3.405 (4) | 135 (5) |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x+1/2, y−1/2, z; (iv) x, −y+2, z+1/2; (v) x+1/2, −y+3/2, z+1/2.
Funding Statement
This work was funded by National Science Foundation, Directorate for Education and Human Resources grant 0942850 to Dean H. Johnston.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, 1, 2, 3, 4, 5. DOI: 10.1107/S2056989021008264/zl5023sup1.cif
Structure factors: contains datablock(s) 1. DOI: 10.1107/S2056989021008264/zl50231sup2.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50231sup7.mol
Structure factors: contains datablock(s) 2. DOI: 10.1107/S2056989021008264/zl50232sup3.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50232sup8.mol
Structure factors: contains datablock(s) 3. DOI: 10.1107/S2056989021008264/zl50233sup4.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50233sup9.mol
Supporting information file. DOI: 10.1107/S2056989021008264/zl50234sup10.mol
Structure factors: contains datablock(s) 4. DOI: 10.1107/S2056989021008264/zl50234sup5.hkl
Supporting information file. DOI: 10.1107/S2056989021008264/zl50235sup11.mol
Structure factors: contains datablock(s) 5. DOI: 10.1107/S2056989021008264/zl50235sup6.hkl
Additional supporting information: crystallographic information; 3D view; checkCIF report