research communications
cis-aquachlorido(rac-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N)chromium(III) tetrachloridozincate trihydrate from synchrotron data
ofaPohang Accelerator Laboratory, POSTECH, Pohang 37673, Republic of Korea, and bDepartment of Chemistry, Andong National University, Andong 36729, Republic of Korea
*Correspondence e-mail: jhchoi@anu.ac.kr
The structure of the title compound, cis-[CrCl(cycb)(H2O)][ZnCl4]·3H2O (cycb is rac-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane; C16H36N4), has been determined from synchrotron data. In the complex cation, the CrIII ion is bound by four N atoms from the tetradentate cycb ligand, a chloride ion and one water molecule in a cis arrangement, displaying a distorted octahedral coordination geometry. The distorted tetrahedral [ZnCl4]2− anion and three additional water molecules remain outside the coordination sphere. The Cr—N(cycb) bond lengths are in the range of 2.0837 (14) to 2.1399 (12) Å while the Cr—Cl and Cr—(OH2) bond lengths are 2.2940 (8) and 2.0082 (13) Å, respectively. The crystal packing is stabilized by hydrogen-bonding interactions between the N—H groups of the macrocyclic ligand, the O—H groups of the water molecules and the Cl atoms of the tetrachloridozincate anion, leading to the formation of a three-dimensional network.
Keywords: crystal structure; synchrotron radiation; macrocyclic chromium(III) complex; chlorido ligand; aqua ligand; cis-geometry; hydrogen bonding.
CCDC reference: 1419197
1. Chemical context
Chromium(III) complexes containing C-meso or racemic-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane (cyca and cycb) ligands are known to exist in trans or cis octahedral coordination geometries when combined with two auxiliary ligands (House et al., 1983; Eriksen & Mønsted, 1983). The cycb ligand readily folds to form the cis isomer while the cyca ligand only folds with difficulty into the trans isomer. There are five conformational trans isomers for the cyclam moiety which differ in the of the sec-NH group (Choi, 2009). Ligands with trans-I, trans-II or trans-V configurations can fold into cis-I, cis-II and cis-V isomers, respectively (Subhan et al., 2011). Infrared and electronic absorption spectral properties are useful in determining the geometric isomers of CrIII complexes with mixed ligands (Choi et al., 2004; Choi & Moon, 2014; Moon & Choi, 2015). However, it should be noted that the geometric assignments based on spectroscopic studies alone are less conclusive. In order to study the molecular structure and crystal packing mode of a complex containing CrIII, the cycb ligand and a ZnCl42− counter-anion, we report herein on the preparation and of cis-[CrCl(cycb)(OH2)]ZnCl4·3H2O, (I).
2. Structural commentary
In the molecular structure of the complex cation, there is one chlorine atom and one water molecule coordinating the CrIII ion with an O1A—Cr1A—Cl1A bond angle of 85.74 (4)°. The rest of the coordination sites are occupied by four nitrogen atoms of the tetradentate macrocyclic cycb ligand, giving rise to a distorted octahedral coordination sphere.
The cycb ligand is folded about the N2A—Cr1A—N4A line and is in its most stable cis-V conformation (Fig. 1). The Cr—N(cycb) bond lengths are in the range 2.0837 (14) to 2.1399 (12) Å, in good agreement with those observed in cis-[Cr(OH)2(cycb)]ClO4·2H2O [2.140–2.142 Å; Bang & Mønsted, 1984], cis-[Cr(NCS)2(cycb)]ClO4·H2O [2.103 (4)–2.147 (4) Å; Byun et al., 2005], cis-[Cr(O2CO)(cycb)]Br·H2O [2.093 (3)–2.115 (3) Å; Dobrzańska, 2005], cis-[Cr(CN)2(cycb)]Cl [2.119 (3)–2.135 (2) Å; Lessard et al., 1992], or cis-[Cr(acac)(cycb)]ClO4·0.5H2O [acac is acetylacetonate; 2.107 (3)–2.133 (3) Å; Byun & Han, 2005]. The Cr—Cl and Cr—(OH2) bond lengths are 2.2940 (8) and 2.0082 (13) Å, respectively. The Cr—Cl bond is slightly shorter than in trans-[CrCl(cyca)(OH2)](NO3)2 [2.307 (2) Å; Temple et al., 1984] or trans-[CrCl2(Me2tn)2]Cl [Me2tn = 2,2-dimethylpropane-1,3-diamine; 2.3253 (7); Choi et al., 2007]. The length of the Cr—(OH2) bond in the title compound is comparable to the values of 2.090 (6) and 1.996 (4) Å found in trans–[CrCl(cyca)(OH2)](NO3)2 (Temple et al., 1984) and trans-[CrF(3,2,3-tet)(OH2)](ClO4)2·H2O (3,2,3-tet = 1,5,8,12-tetraazaundecane; Choi & Lee, 2008), respectively. The Cl1A—Cr1A—N1 and O1A—Cr1A—N3A angles are 170.35 (3) and 172.43 (5)°, respectively. The angles N1A—Cr1A—N2A and N3A—Cr1A—N4A are 87.01 (5) and 87.77 (5)°, reflecting the distorted octahedral coordination sphere. The tetrahedral [ZnCl4]2− anion and three additional water molecules remain outside the coordination sphere of CrIII. The complex anion is distorted due to its involvement in hydrogen-bonding interactions. Zn—Cl bonds in the anion span a range from 2.2569 (7) to 2.3131 (8) Å, and the Cl—Zn—Cl angles from 106.02 (4) to 111.49 (3)°.
3. Supramolecular features
Extensive hydrogen-bonding interactions occur in the ). The supramolecular architecture involves hydrogen-bonding interactions including the N—H groups of the macrocycles, the O—H groups of coordinating and lattice water molecules as donors, and the anion Cl atoms and O atoms of coordinating and lattice water molecules as acceptors, giving rise to a three-dimensional network structure (Fig. 2).
(Table 14. Database survey
A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014) gave 13 hits for CrIII complexes involving the macrocyclic rac-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane ligand. The crystal structures of cis-[Cr(OH)2(cycb)]ClO4·2H2O (Bang & Mønsted, 1984), cis-[Cr(NCS)2(cycb)]ClO4·H2O (Byun et al., 2005), cis-[Cr(O2CO)(cycb)]Br·H2O (Dobrzanska, 2005) cis-[Cr(CN)2(cycb)]Cl (Lessard et al., 1992), cis-[Cr(acac)(cycb)]ClO4·0.5H2O (Byun & Han, 2005), trans–[CrCl(cyca)(OH2)](NO3)2 (Temple et al., 1984) and trans-[Cr(OH)(cyca)(OH2)](ClO4)2·H2O (Goodson et al., 2001) have been reported previously. However, no of the [CrCl(cycb)(OH2)]2+ cationic complex with any anion was found, although the preparation of cis-[CrCl(cycb)(OH2)](ClO4)2·0.4HClO4·3H2O has been reported (Eriksen & Mønsted, 1983).
5. Synthesis and crystallization
All chemicals were reagent grade materials and used without further purification. The starting material, cis-[CrCl2(cycb)]Cl·H2O was prepared according to literature procedures (Eriksen & Mønsted, 1983). Crude cis-[CrCl2(cycb)]Cl·H2O (0.07 g) was dissolved in 4 mL of 0.01 M HCl at 353 K and the 1 mL of 6 M HCl containing 0.15 g of solid ZnCl2 were added to this solution. The mixture was refluxed for 30 min and then cooled to room temperature. The resulting solution was filtered and the filtrate was allowed to stand at room temperature for one day to afford purple crystals of compound (I) suitable for X-ray structural analysis.
6. Refinement
Crystal data, data collection and structure . H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.96–0.98 Å and N—H = 0.98 Å, and with Uiso(H) values of 1.2 or 1.5 × Ueq of the parent atoms. The hydrogen atoms of water molecules were located in difference maps restrained with O—H = 0.84 Å using DFIX and DANG commands.
details are summarized in Table 2
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Supporting information
CCDC reference: 1419197
https://doi.org/10.1107/S2056989015015212/wm5196sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015015212/wm5196Isup2.hkl
Data collection: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983); cell
HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).[CrCl(C16H38N4O)(H2O)][ZnCl4]3H2O | Z = 2 |
Mr = 651.17 | F(000) = 678 |
Triclinic, P1 | Dx = 1.563 Mg m−3 |
a = 9.1010 (18) Å | Synchrotron radiation, λ = 0.610 Å |
b = 9.5830 (19) Å | Cell parameters from 68409 reflections |
c = 17.007 (3) Å | θ = 0.4–33.7° |
α = 81.73 (3)° | µ = 1.16 mm−1 |
β = 75.80 (3)° | T = 260 K |
γ = 74.90 (3)° | Plate, purple |
V = 1383.2 (6) Å3 | 0.22 × 0.16 × 0.08 mm |
ADSC Q210 CCD area detector diffractometer | 7053 reflections with I > 2σ(I) |
Radiation source: PLSII 2D bending magnet | Rint = 0.013 |
ω scan | θmax = 25.0°, θmin = 2.3° |
Absorption correction: empirical (using intensity measurements) (HKL3000sm SCALEAPCK; Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.787, Tmax = 0.917 | k = −13→13 |
14317 measured reflections | l = −23→23 |
7413 independent reflections |
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0439P)2 + 0.7948P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7413 reflections | Δρmax = 0.76 e Å−3 |
310 parameters | Δρmin = −0.56 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cr1A | 0.87300 (2) | 0.33415 (2) | 0.22043 (2) | 0.01468 (5) | |
O1A | 0.69575 (12) | 0.46877 (12) | 0.28842 (7) | 0.0251 (2) | |
H1OA | 0.697 (2) | 0.5566 (12) | 0.2814 (12) | 0.030* | |
H2OA | 0.6213 (18) | 0.456 (2) | 0.3265 (9) | 0.030* | |
N1A | 0.81211 (13) | 0.15969 (13) | 0.30221 (7) | 0.0189 (2) | |
H1NA | 0.8881 | 0.0712 | 0.2837 | 0.023* | |
N2A | 1.05645 (13) | 0.31721 (13) | 0.28159 (7) | 0.0203 (2) | |
H2NA | 1.0888 | 0.4090 | 0.2658 | 0.024* | |
N3A | 1.04622 (12) | 0.20987 (12) | 0.13663 (7) | 0.01725 (19) | |
H3NA | 1.0404 | 0.1085 | 0.1514 | 0.021* | |
N4A | 0.70640 (12) | 0.30026 (12) | 0.15997 (7) | 0.01734 (19) | |
H4NA | 0.6126 | 0.3769 | 0.1762 | 0.021* | |
C1A | 0.65887 (16) | 0.14998 (17) | 0.28964 (9) | 0.0235 (3) | |
H1A1 | 0.5768 | 0.2272 | 0.3153 | 0.028* | |
H1A2 | 0.6365 | 0.0579 | 0.3143 | 0.028* | |
C2A | 0.80792 (17) | 0.16149 (17) | 0.39133 (8) | 0.0240 (3) | |
H2A | 0.7315 | 0.2485 | 0.4116 | 0.029* | |
C3A | 0.7586 (2) | 0.0277 (2) | 0.44022 (11) | 0.0397 (4) | |
H3A1 | 0.6521 | 0.0331 | 0.4397 | 0.060* | |
H3A2 | 0.7689 | 0.0244 | 0.4954 | 0.060* | |
H3A3 | 0.8241 | −0.0582 | 0.4162 | 0.060* | |
C4A | 0.96572 (18) | 0.16400 (17) | 0.40594 (9) | 0.0265 (3) | |
H4A1 | 1.0411 | 0.0803 | 0.3827 | 0.032* | |
H4A2 | 0.9586 | 0.1505 | 0.4643 | 0.032* | |
C5A | 1.03257 (18) | 0.29722 (17) | 0.37339 (9) | 0.0261 (3) | |
C6A | 0.9269 (2) | 0.4363 (2) | 0.40828 (10) | 0.0368 (4) | |
H6A1 | 0.9717 | 0.5170 | 0.3845 | 0.055* | |
H6A2 | 0.9165 | 0.4277 | 0.4662 | 0.055* | |
H6A3 | 0.8260 | 0.4517 | 0.3961 | 0.055* | |
C7A | 1.1889 (2) | 0.2726 (2) | 0.39878 (11) | 0.0404 (4) | |
H7A1 | 1.2530 | 0.1795 | 0.3840 | 0.061* | |
H7A2 | 1.1702 | 0.2759 | 0.4566 | 0.061* | |
H7A3 | 1.2411 | 0.3470 | 0.3716 | 0.061* | |
C8A | 1.18917 (16) | 0.20584 (17) | 0.24069 (9) | 0.0252 (3) | |
H8A1 | 1.1756 | 0.1097 | 0.2626 | 0.030* | |
H8A2 | 1.2858 | 0.2164 | 0.2509 | 0.030* | |
C9A | 1.19721 (15) | 0.22306 (16) | 0.15068 (9) | 0.0227 (3) | |
H9A1 | 1.2163 | 0.3171 | 0.1280 | 0.027* | |
H9A2 | 1.2820 | 0.1488 | 0.1242 | 0.027* | |
C10A | 1.03870 (15) | 0.24351 (15) | 0.04815 (8) | 0.0200 (2) | |
H10A | 1.0335 | 0.3471 | 0.0335 | 0.024* | |
C11A | 1.18404 (18) | 0.15683 (19) | −0.00605 (9) | 0.0297 (3) | |
H11A | 1.2726 | 0.1933 | −0.0057 | 0.045* | |
H11B | 1.1691 | 0.1664 | −0.0607 | 0.045* | |
H11C | 1.2016 | 0.0564 | 0.0142 | 0.045* | |
C12A | 0.89375 (16) | 0.20959 (17) | 0.03353 (8) | 0.0237 (3) | |
H12A | 0.8925 | 0.1108 | 0.0559 | 0.028* | |
H12B | 0.9051 | 0.2119 | −0.0248 | 0.028* | |
C13A | 0.73394 (15) | 0.30643 (16) | 0.06770 (8) | 0.0214 (2) | |
C14A | 0.71987 (19) | 0.46457 (18) | 0.03395 (10) | 0.0304 (3) | |
H14A | 0.6183 | 0.5209 | 0.0569 | 0.046* | |
H14B | 0.7345 | 0.4711 | −0.0242 | 0.046* | |
H14C | 0.7979 | 0.5012 | 0.0480 | 0.046* | |
C15A | 0.60817 (18) | 0.2528 (2) | 0.04261 (10) | 0.0312 (3) | |
H15A | 0.6160 | 0.1523 | 0.0615 | 0.047* | |
H15B | 0.6232 | 0.2639 | −0.0156 | 0.047* | |
H15C | 0.5069 | 0.3087 | 0.0663 | 0.047* | |
C16A | 0.66416 (16) | 0.16285 (16) | 0.19998 (8) | 0.0225 (3) | |
H16A | 0.7403 | 0.0808 | 0.1754 | 0.027* | |
H16B | 0.5631 | 0.1610 | 0.1916 | 0.027* | |
Zn1B | 0.26864 (2) | 0.74837 (2) | 0.24042 (2) | 0.02510 (6) | |
Cl1A | 0.93837 (4) | 0.54067 (4) | 0.15097 (2) | 0.02727 (8) | |
Cl1B | 0.22710 (8) | 0.75375 (7) | 0.37777 (3) | 0.05834 (16) | |
Cl2B | 0.33787 (5) | 0.51602 (4) | 0.20871 (3) | 0.03437 (9) | |
Cl3B | 0.03474 (4) | 0.86751 (4) | 0.20538 (3) | 0.03322 (9) | |
Cl4B | 0.45104 (6) | 0.87103 (6) | 0.17503 (4) | 0.05119 (14) | |
O1W | 0.70053 (18) | 0.75266 (16) | 0.28427 (10) | 0.0450 (3) | |
H1O1 | 0.639 (2) | 0.776 (3) | 0.2521 (13) | 0.054* | |
H2O1 | 0.7866 (17) | 0.766 (3) | 0.2551 (13) | 0.054* | |
O2W | 0.46628 (19) | 0.4464 (2) | 0.41394 (11) | 0.0582 (4) | |
H1O2 | 0.482 (4) | 0.513 (2) | 0.4363 (16) | 0.070* | |
H2O2 | 0.446 (4) | 0.389 (3) | 0.4566 (12) | 0.070* | |
O3W | 0.4581 (3) | 0.2496 (3) | 0.54916 (14) | 0.0858 (7) | |
H1O3 | 0.389 (3) | 0.247 (5) | 0.5950 (13) | 0.103* | |
H2O3 | 0.540 (3) | 0.254 (5) | 0.565 (2) | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1A | 0.01303 (9) | 0.01372 (10) | 0.01588 (9) | −0.00341 (7) | −0.00166 (7) | 0.00118 (7) |
O1A | 0.0238 (5) | 0.0196 (5) | 0.0268 (5) | −0.0031 (4) | 0.0030 (4) | −0.0036 (4) |
N1A | 0.0197 (5) | 0.0179 (5) | 0.0180 (5) | −0.0061 (4) | −0.0029 (4) | 0.0026 (4) |
N2A | 0.0199 (5) | 0.0213 (6) | 0.0211 (5) | −0.0073 (4) | −0.0066 (4) | 0.0018 (4) |
N3A | 0.0140 (4) | 0.0163 (5) | 0.0194 (5) | −0.0034 (4) | −0.0011 (4) | 0.0002 (4) |
N4A | 0.0138 (4) | 0.0179 (5) | 0.0188 (5) | −0.0025 (4) | −0.0030 (4) | 0.0003 (4) |
C1A | 0.0207 (6) | 0.0261 (7) | 0.0243 (6) | −0.0118 (5) | −0.0024 (5) | 0.0033 (5) |
C2A | 0.0271 (6) | 0.0260 (7) | 0.0174 (6) | −0.0083 (5) | −0.0031 (5) | 0.0041 (5) |
C3A | 0.0512 (10) | 0.0427 (10) | 0.0282 (8) | −0.0253 (9) | −0.0096 (7) | 0.0156 (7) |
C4A | 0.0307 (7) | 0.0277 (7) | 0.0212 (6) | −0.0081 (6) | −0.0089 (5) | 0.0054 (5) |
C5A | 0.0309 (7) | 0.0294 (7) | 0.0218 (6) | −0.0109 (6) | −0.0111 (5) | 0.0018 (5) |
C6A | 0.0519 (10) | 0.0344 (9) | 0.0285 (7) | −0.0128 (8) | −0.0108 (7) | −0.0079 (6) |
C7A | 0.0419 (9) | 0.0540 (11) | 0.0353 (8) | −0.0216 (8) | −0.0229 (7) | 0.0080 (8) |
C8A | 0.0169 (5) | 0.0281 (7) | 0.0297 (7) | −0.0023 (5) | −0.0081 (5) | 0.0004 (5) |
C9A | 0.0129 (5) | 0.0260 (7) | 0.0270 (6) | −0.0039 (5) | −0.0023 (4) | −0.0003 (5) |
C10A | 0.0182 (5) | 0.0206 (6) | 0.0179 (5) | −0.0029 (5) | −0.0003 (4) | −0.0005 (4) |
C11A | 0.0228 (6) | 0.0346 (8) | 0.0259 (7) | −0.0015 (6) | 0.0031 (5) | −0.0082 (6) |
C12A | 0.0208 (6) | 0.0283 (7) | 0.0213 (6) | −0.0039 (5) | −0.0033 (5) | −0.0059 (5) |
C13A | 0.0187 (5) | 0.0254 (7) | 0.0192 (6) | −0.0029 (5) | −0.0059 (4) | −0.0001 (5) |
C14A | 0.0292 (7) | 0.0299 (8) | 0.0279 (7) | −0.0032 (6) | −0.0087 (6) | 0.0091 (6) |
C15A | 0.0236 (6) | 0.0428 (9) | 0.0302 (7) | −0.0063 (6) | −0.0121 (6) | −0.0044 (6) |
C16A | 0.0210 (6) | 0.0235 (7) | 0.0250 (6) | −0.0103 (5) | −0.0056 (5) | 0.0016 (5) |
Zn1B | 0.02438 (9) | 0.02053 (9) | 0.02709 (9) | −0.00146 (6) | −0.00336 (6) | −0.00237 (6) |
Cl1A | 0.03019 (17) | 0.02080 (16) | 0.02835 (16) | −0.00789 (13) | −0.00262 (13) | 0.00291 (12) |
Cl1B | 0.0683 (3) | 0.0656 (4) | 0.0287 (2) | 0.0098 (3) | −0.0092 (2) | −0.0134 (2) |
Cl2B | 0.02746 (17) | 0.02228 (18) | 0.0507 (2) | −0.00162 (14) | −0.00473 (15) | −0.00905 (15) |
Cl3B | 0.02720 (17) | 0.02074 (17) | 0.0509 (2) | −0.00139 (13) | −0.01244 (15) | −0.00133 (15) |
Cl4B | 0.0334 (2) | 0.0375 (3) | 0.0755 (4) | −0.01276 (19) | −0.0026 (2) | 0.0102 (2) |
O1W | 0.0402 (7) | 0.0364 (7) | 0.0533 (8) | −0.0088 (6) | 0.0012 (6) | −0.0074 (6) |
O2W | 0.0380 (7) | 0.0645 (11) | 0.0563 (10) | −0.0082 (7) | 0.0090 (7) | 0.0051 (8) |
O3W | 0.0905 (17) | 0.1024 (19) | 0.0614 (13) | −0.0315 (15) | 0.0022 (11) | −0.0132 (12) |
Cr1A—O1A | 2.0082 (13) | C7A—H7A1 | 0.9600 |
Cr1A—N3A | 2.0837 (14) | C7A—H7A2 | 0.9600 |
Cr1A—N1A | 2.1147 (13) | C7A—H7A3 | 0.9600 |
Cr1A—N2A | 2.1352 (12) | C8A—C9A | 1.502 (2) |
Cr1A—N4A | 2.1399 (12) | C8A—H8A1 | 0.9700 |
Cr1A—Cl1A | 2.2940 (8) | C8A—H8A2 | 0.9700 |
O1A—H1OA | 0.835 (9) | C9A—H9A1 | 0.9700 |
O1A—H2OA | 0.835 (9) | C9A—H9A2 | 0.9700 |
N1A—C1A | 1.4896 (17) | C10A—C12A | 1.5217 (19) |
N1A—C2A | 1.5093 (17) | C10A—C11A | 1.529 (2) |
N1A—H1NA | 0.9800 | C10A—H10A | 0.9800 |
N2A—C8A | 1.487 (2) | C11A—H11A | 0.9600 |
N2A—C5A | 1.5134 (18) | C11A—H11B | 0.9600 |
N2A—H2NA | 0.9800 | C11A—H11C | 0.9600 |
N3A—C9A | 1.4905 (16) | C12A—C13A | 1.533 (2) |
N3A—C10A | 1.5074 (17) | C12A—H12A | 0.9700 |
N3A—H3NA | 0.9800 | C12A—H12B | 0.9700 |
N4A—C16A | 1.4909 (17) | C13A—C14A | 1.526 (2) |
N4A—C13A | 1.5221 (17) | C13A—C15A | 1.538 (2) |
N4A—H4NA | 0.9800 | C14A—H14A | 0.9600 |
C1A—C16A | 1.502 (2) | C14A—H14B | 0.9600 |
C1A—H1A1 | 0.9700 | C14A—H14C | 0.9600 |
C1A—H1A2 | 0.9700 | C15A—H15A | 0.9600 |
C2A—C4A | 1.523 (2) | C15A—H15B | 0.9600 |
C2A—C3A | 1.532 (2) | C15A—H15C | 0.9600 |
C2A—H2A | 0.9800 | C16A—H16A | 0.9700 |
C3A—H3A1 | 0.9600 | C16A—H16B | 0.9700 |
C3A—H3A2 | 0.9600 | Zn1B—Cl2B | 2.2569 (7) |
C3A—H3A3 | 0.9600 | Zn1B—Cl4B | 2.2603 (9) |
C4A—C5A | 1.531 (2) | Zn1B—Cl1B | 2.2789 (7) |
C4A—H4A1 | 0.9700 | Zn1B—Cl3B | 2.3131 (8) |
C4A—H4A2 | 0.9700 | O1W—H1O1 | 0.847 (9) |
C5A—C6A | 1.528 (3) | O1W—H2O1 | 0.848 (9) |
C5A—C7A | 1.537 (2) | O2W—H1O2 | 0.845 (10) |
C6A—H6A1 | 0.9600 | O2W—H2O2 | 0.859 (10) |
C6A—H6A2 | 0.9600 | O3W—H1O3 | 0.874 (10) |
C6A—H6A3 | 0.9600 | O3W—H2O3 | 0.870 (10) |
O1A—Cr1A—N3A | 172.43 (5) | H6A1—C6A—H6A2 | 109.5 |
O1A—Cr1A—N1A | 88.19 (5) | C5A—C6A—H6A3 | 109.5 |
N3A—Cr1A—N1A | 97.08 (5) | H6A1—C6A—H6A3 | 109.5 |
O1A—Cr1A—N2A | 101.33 (5) | H6A2—C6A—H6A3 | 109.5 |
N3A—Cr1A—N2A | 84.43 (5) | C5A—C7A—H7A1 | 109.5 |
N1A—Cr1A—N2A | 87.01 (5) | C5A—C7A—H7A2 | 109.5 |
O1A—Cr1A—N4A | 87.37 (5) | H7A1—C7A—H7A2 | 109.5 |
N3A—Cr1A—N4A | 87.77 (5) | C5A—C7A—H7A3 | 109.5 |
N1A—Cr1A—N4A | 84.11 (5) | H7A1—C7A—H7A3 | 109.5 |
N2A—Cr1A—N4A | 167.37 (5) | H7A2—C7A—H7A3 | 109.5 |
O1A—Cr1A—Cl1A | 85.74 (4) | N2A—C8A—C9A | 109.92 (12) |
N3A—Cr1A—Cl1A | 89.71 (4) | N2A—C8A—H8A1 | 109.7 |
N1A—Cr1A—Cl1A | 170.35 (3) | C9A—C8A—H8A1 | 109.7 |
N2A—Cr1A—Cl1A | 86.83 (4) | N2A—C8A—H8A2 | 109.7 |
N4A—Cr1A—Cl1A | 103.07 (4) | C9A—C8A—H8A2 | 109.7 |
Cr1A—O1A—H1OA | 116.7 (14) | H8A1—C8A—H8A2 | 108.2 |
Cr1A—O1A—H2OA | 133.8 (14) | N3A—C9A—C8A | 108.68 (11) |
H1OA—O1A—H2OA | 109.3 (17) | N3A—C9A—H9A1 | 110.0 |
C1A—N1A—C2A | 111.26 (11) | C8A—C9A—H9A1 | 110.0 |
C1A—N1A—Cr1A | 105.43 (8) | N3A—C9A—H9A2 | 110.0 |
C2A—N1A—Cr1A | 118.74 (9) | C8A—C9A—H9A2 | 110.0 |
C1A—N1A—H1NA | 106.9 | H9A1—C9A—H9A2 | 108.3 |
C2A—N1A—H1NA | 106.9 | N3A—C10A—C12A | 110.54 (11) |
Cr1A—N1A—H1NA | 106.9 | N3A—C10A—C11A | 110.80 (12) |
C8A—N2A—C5A | 112.59 (12) | C12A—C10A—C11A | 109.63 (12) |
C8A—N2A—Cr1A | 105.17 (9) | N3A—C10A—H10A | 108.6 |
C5A—N2A—Cr1A | 122.52 (9) | C12A—C10A—H10A | 108.6 |
C8A—N2A—H2NA | 105.0 | C11A—C10A—H10A | 108.6 |
C5A—N2A—H2NA | 105.0 | C10A—C11A—H11A | 109.5 |
Cr1A—N2A—H2NA | 105.0 | C10A—C11A—H11B | 109.5 |
C9A—N3A—C10A | 111.61 (10) | H11A—C11A—H11B | 109.5 |
C9A—N3A—Cr1A | 105.81 (8) | C10A—C11A—H11C | 109.5 |
C10A—N3A—Cr1A | 117.28 (8) | H11A—C11A—H11C | 109.5 |
C9A—N3A—H3NA | 107.2 | H11B—C11A—H11C | 109.5 |
C10A—N3A—H3NA | 107.2 | C10A—C12A—C13A | 118.61 (12) |
Cr1A—N3A—H3NA | 107.2 | C10A—C12A—H12A | 107.7 |
C16A—N4A—C13A | 111.76 (11) | C13A—C12A—H12A | 107.7 |
C16A—N4A—Cr1A | 105.83 (8) | C10A—C12A—H12B | 107.7 |
C13A—N4A—Cr1A | 122.60 (8) | C13A—C12A—H12B | 107.7 |
C16A—N4A—H4NA | 105.1 | H12A—C12A—H12B | 107.1 |
C13A—N4A—H4NA | 105.1 | N4A—C13A—C14A | 108.13 (12) |
Cr1A—N4A—H4NA | 105.1 | N4A—C13A—C12A | 109.83 (11) |
N1A—C1A—C16A | 109.24 (11) | C14A—C13A—C12A | 112.37 (12) |
N1A—C1A—H1A1 | 109.8 | N4A—C13A—C15A | 110.71 (11) |
C16A—C1A—H1A1 | 109.8 | C14A—C13A—C15A | 107.32 (12) |
N1A—C1A—H1A2 | 109.8 | C12A—C13A—C15A | 108.47 (12) |
C16A—C1A—H1A2 | 109.8 | C13A—C14A—H14A | 109.5 |
H1A1—C1A—H1A2 | 108.3 | C13A—C14A—H14B | 109.5 |
N1A—C2A—C4A | 112.13 (11) | H14A—C14A—H14B | 109.5 |
N1A—C2A—C3A | 110.63 (13) | C13A—C14A—H14C | 109.5 |
C4A—C2A—C3A | 108.18 (13) | H14A—C14A—H14C | 109.5 |
N1A—C2A—H2A | 108.6 | H14B—C14A—H14C | 109.5 |
C4A—C2A—H2A | 108.6 | C13A—C15A—H15A | 109.5 |
C3A—C2A—H2A | 108.6 | C13A—C15A—H15B | 109.5 |
C2A—C3A—H3A1 | 109.5 | H15A—C15A—H15B | 109.5 |
C2A—C3A—H3A2 | 109.5 | C13A—C15A—H15C | 109.5 |
H3A1—C3A—H3A2 | 109.5 | H15A—C15A—H15C | 109.5 |
C2A—C3A—H3A3 | 109.5 | H15B—C15A—H15C | 109.5 |
H3A1—C3A—H3A3 | 109.5 | N4A—C16A—C1A | 110.80 (11) |
H3A2—C3A—H3A3 | 109.5 | N4A—C16A—H16A | 109.5 |
C2A—C4A—C5A | 119.11 (12) | C1A—C16A—H16A | 109.5 |
C2A—C4A—H4A1 | 107.5 | N4A—C16A—H16B | 109.5 |
C5A—C4A—H4A1 | 107.5 | C1A—C16A—H16B | 109.5 |
C2A—C4A—H4A2 | 107.5 | H16A—C16A—H16B | 108.1 |
C5A—C4A—H4A2 | 107.5 | Cl2B—Zn1B—Cl4B | 111.49 (3) |
H4A1—C4A—H4A2 | 107.0 | Cl2B—Zn1B—Cl1B | 109.60 (4) |
N2A—C5A—C6A | 108.55 (13) | Cl4B—Zn1B—Cl1B | 110.65 (4) |
N2A—C5A—C4A | 109.66 (12) | Cl2B—Zn1B—Cl3B | 110.73 (3) |
C6A—C5A—C4A | 112.68 (14) | Cl4B—Zn1B—Cl3B | 108.19 (3) |
N2A—C5A—C7A | 110.36 (13) | Cl1B—Zn1B—Cl3B | 106.02 (4) |
C6A—C5A—C7A | 107.49 (14) | H1O1—O1W—H2O1 | 104.5 (18) |
C4A—C5A—C7A | 108.08 (13) | H1O2—O2W—H2O2 | 98.6 (19) |
C5A—C6A—H6A1 | 109.5 | H1O3—O3W—H2O3 | 102 (2) |
C5A—C6A—H6A2 | 109.5 | ||
C2A—N1A—C1A—C16A | 174.65 (12) | Cr1A—N3A—C9A—C8A | 44.64 (12) |
Cr1A—N1A—C1A—C16A | 44.67 (13) | N2A—C8A—C9A—N3A | −58.03 (15) |
C1A—N1A—C2A—C4A | 177.23 (12) | C9A—N3A—C10A—C12A | 172.32 (11) |
Cr1A—N1A—C2A—C4A | −60.17 (15) | Cr1A—N3A—C10A—C12A | −65.41 (13) |
C1A—N1A—C2A—C3A | 56.37 (16) | C9A—N3A—C10A—C11A | 50.58 (15) |
Cr1A—N1A—C2A—C3A | 178.97 (11) | Cr1A—N3A—C10A—C11A | 172.84 (9) |
N1A—C2A—C4A—C5A | 65.83 (18) | N3A—C10A—C12A—C13A | 70.03 (16) |
C3A—C2A—C4A—C5A | −171.90 (14) | C11A—C10A—C12A—C13A | −167.54 (13) |
C8A—N2A—C5A—C6A | 164.61 (12) | C16A—N4A—C13A—C14A | 160.54 (11) |
Cr1A—N2A—C5A—C6A | −68.42 (15) | Cr1A—N4A—C13A—C14A | −72.31 (13) |
C8A—N2A—C5A—C4A | −71.90 (15) | C16A—N4A—C13A—C12A | −76.51 (13) |
Cr1A—N2A—C5A—C4A | 55.07 (15) | Cr1A—N4A—C13A—C12A | 50.64 (14) |
C8A—N2A—C5A—C7A | 47.05 (17) | C16A—N4A—C13A—C15A | 43.25 (15) |
Cr1A—N2A—C5A—C7A | 174.03 (11) | Cr1A—N4A—C13A—C15A | 170.39 (10) |
C2A—C4A—C5A—N2A | −61.30 (18) | C10A—C12A—C13A—N4A | −60.60 (16) |
C2A—C4A—C5A—C6A | 59.73 (18) | C10A—C12A—C13A—C14A | 59.80 (16) |
C2A—C4A—C5A—C7A | 178.35 (14) | C10A—C12A—C13A—C15A | 178.28 (12) |
C5A—N2A—C8A—C9A | 174.68 (11) | C13A—N4A—C16A—C1A | 172.31 (11) |
Cr1A—N2A—C8A—C9A | 38.95 (12) | Cr1A—N4A—C16A—C1A | 36.58 (12) |
C10A—N3A—C9A—C8A | 173.29 (11) | N1A—C1A—C16A—N4A | −56.58 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O1W | 0.84 (1) | 1.90 (1) | 2.7227 (19) | 170 (2) |
O1A—H2OA···O2W | 0.84 (1) | 1.79 (1) | 2.623 (2) | 173 (2) |
N1A—H1NA···Cl3Bi | 0.98 | 2.43 | 3.3748 (18) | 163 |
N2A—H2NA···Cl2Bii | 0.98 | 2.64 | 3.4686 (16) | 142 |
N3A—H3NA···Cl3Bi | 0.98 | 2.37 | 3.3403 (15) | 172 |
N4A—H4NA···Cl2B | 0.98 | 2.48 | 3.4244 (17) | 163 |
O1W—H1O1···Cl4B | 0.85 (1) | 2.33 (1) | 3.165 (2) | 171 (3) |
O1W—H2O1···Cl3Bii | 0.85 (1) | 2.59 (1) | 3.4029 (18) | 160 (2) |
O2W—H2O2···O3W | 0.86 (1) | 1.92 (1) | 2.756 (3) | 165 (3) |
O3W—H1O3···O1Wiii | 0.87 (1) | 2.02 (2) | 2.846 (3) | 158 (3) |
O3W—H2O3···Cl1Biii | 0.87 (1) | 2.52 (1) | 3.383 (3) | 174 (4) |
Symmetry codes: (i) x+1, y−1, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
This research was supported by a grant from 2015 International Academic Exchange Program of Andong National University. The X-ray crystallography experiment at PLS-II BL2D-SMC beamline was supported in part by MSIP and POSTECH.
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