research communications
trans-diammine(1,4,8,11-tetraazacyclotetradecane-κ4N)chromium(III) tetrachloridozincate chloride monohydrate 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 10H24N4)(NH3)2][ZnCl4]Cl·H2O, is comprised of four halves of the CrIII complex cations (the counterparts being generated by application of inversion symmetry), two tetrachloridozincate anions, two chloride anions and two water molecules. Each CrIII ion is coordinated by the four N atoms of the cyclam (1,4,8,11-tetraazacyclotetradecane) ligand in the equatorial plane and by two N atoms of ammine ligands in axial positions, displaying an overall distorted octahedral coordination environment. The Cr—N(cyclam) bond lengths range from 2.0501 (15) to 2.0615 (15) Å, while the Cr—(NH3) bond lengths range from 2.0976 (13) to 2.1062 (13) Å. The macrocyclic cyclam moieties adopt the trans-III conformation with six- and five-membered chelate rings in chair and gauche conformations. The [ZnCl4]2− anions have a slightly distorted tetrahedral shape. In the crystal, the Cl− anions link the complex cations, as well as the solvent water molecules, through N—H⋯Cl and O—H⋯Cl hydrogen-bonding interactions. The supramolecular set-up also includes N—H⋯Cl, C—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonding between N—H or C—H groups of cyclam, ammine N—H and water O—H donor groups, and O atoms of the water molecules, Cl− anions or Cl atoms of the [ZnCl4]2− anions as acceptors, leading to a three-dimensional network structure.
of the title complex salt, [Cr(CKeywords: crystal structure; cyclam; ammine ligand; tetrachloridozincate chloride double salt; trans-III conformation; chromium(III) complex.
CCDC reference: 1456673
1. Chemical context
The cyclam macrocycle (1,4,8,11-tetraazacyclotetradecane, C10H24N4) can adopt both planar (trans) and folded (cis) configurations (Poon & Pun, 1980). There are five conformational trans isomers for the macrocycle, which differ in the of the sec-NH groups (Choi, 2009). The trans-I, trans-II and trans-V conformations can fold to form cis-I, cis-II and cis-V isomers, respectively (Subhan et al., 2011). Recently, it has been reported that cyclam derivatives and their metal complexes exhibit anti-HIV activity (Ronconi & Sadler, 2007; De Clercq, 2010; Ross et al., 2012) whereby the strength of binding to the CXCR4 receptor correlates with the anti-HIV activity. The conformation of the macrocyclic ligand and the orientations of the N—H bonds are very important factors for co-receptor recognition. Therefore, a deeper knowledge of the conformation and crystal packing of metal complexes containing the cyclam ligand has become important in the development of new highly effective anti-HIV drugs that specifially target alternative events in the HIV replicative cycle (De Clercq, 2010). In addition, counter-anionic species play an important role in chemistry, pharmacy and biology (Flores-Velez et al., 1991; Fabbrizzi & Poggi, 2013). As part of a study on the structural and supramolecular features of chromium(III) complex cations with a macrocyclic ligand and with different anions, we report here the structural characterization of trans-[Cr(NH3)2(cyclam)][ZnCl4]Cl·H2O, (I).
2. Structural commentary
Compound (I) is another example containing a trans-[Cr(NH3)2(cyclam)]3+ moiety but with a different double counter-anion (Derwahl et al., 1999). The of (I) comprises four halves of the CrIII complex cations, two tetrachloridozincate anions, two chloride anions and two water molecules. The four Cr atoms are located on crystallographic centers of symmetry. Since the complex cations have molecular Ci symmetry, the cyclam ligand has a trans-III conformation (Fig. 1). In each of the complex cations, the CrIII ion is coordinated by the nitrogen atoms of the cyclam ligand occupying the equatorial sites. Two ammine ligands complete the distorted trans-configured octahedral coordination sphere at the axial positions. The Cr—N bond lengths including the donor atoms of the cyclam ligand range from 2.0501 (15) to 2.0615 (15) Å, comparable to those determined for trans-[CrCl2(cyclam)]2[ZnCl4] (Flores-Velez et al., 1991), trans-[Cr(nic-O)2(cyclam)]ClO4 (nic-O = O-coordinating nicotinate; Choi, 2009), trans-[CrF2(2,2,3-tet)]ClO4 (2,2,3-tet = 1,4,7,11-tetraazaundecane; Choi & Moon, 2014), [Cr(ox)(cyclam)]ClO4 (ox = oxalate; Choi et al., 2004) or [Cr(acac)(cyclam)](ClO4)2·0.5H2O (acac = acetylacetonate; Subhan et al., 2011). However, the Cr—N bond lengths of the secondary amine group of the cyclam ligands are slightly shorter than those of the primary amine group as determined for trans-[CrCl2(Me2tn)2]2ZnCl4 (Me2tn = 2,2-dimethylpropane-1,3-diamine; Choi et al., 2011), trans-[Cr(N3)2(Me2tn)2]ClO4·2H2O (Moon & Choi, 2015), or trans-[Cr(NCS)2(Me2tn)2]SCN·0.5H2O (Choi & Lee, 2009). The Cr—(NH3) bond lengths range from 2.0976 (13) to 2.1062 (13) Å, similar to the average value of 2.095 (3) Å found in trans-[Cr(NH3)2(cyclam)](ClO4)Cl2 (Derwahl et al., 1999). The five-membered chelate rings of the cyclam ligands adopt gauche and six-membered ring chair conformations. The tetrahedral [ZnCl4]2− anion is distorted due to its involvement in hydrogen-bonding interactions. It exhibits Zn—Cl bond lengths ranging from 2.2238 (10) to 2.3232 (8) Å and Cl—Zn—Cl angles from 105.67 (3) to 115.38 (3)°.
3. Supramolecular features
In the crystal, the complex cations are stacked parallel to the a-axis direction. A series of N—H⋯Cl and C—H⋯Cl hydrogen bonds link the cations to neighboring anions. An extensive array of additional N—H⋯O and O—H⋯Cl contacts including the lattice water molecule generates a three-dimensional network (Table 1, Fig. 2).
4. Database survey
A search in the Cambridge Structural Database (Version 5.36, last update May 2015; Groom & Allen, 2014) gave just one hit for a [Cr(NH3)2(cyclam)]3+ unit, viz. the of trans-[Cr(NH3)2(cyclam)](ClO4)Cl2 (Derwahl et al., 1999). This dichloride perchlorate double salt and the title compound show the same trans-III conformation of the cyclam ligand, however with different hydrogen-bonding and crystal packing networks. The of cis-[Cr(NH3)2(cyclam)]I3·H2O was also found (Kukina et al., 1991), but no structure of any double salt of trans-[Cr(NH3)2(cyclam)]3+ with an additional [ZnCl4]2− anion.
5. Synthesis and crystallization
Cyclam and CrCl3(THF)3 were purchased from Stream Chemicals and used as provided. All chemicals were reagent grade materials and used without further purification. The starting material, trans-[Cr(NH3)2(cyclam)](PF6)(NO3)·0.5H2O, was prepared according to a previously described procedure (Kane-Maguire et al., 1985). The hexafluoridophosphate nitrate double salt (0.042 g) was dissolved in 5 ml of 0.01 M HCl and added to 2 ml of 1 M HCl containing 0.12 g of solid ZnCl2. The resulting solution was filtered and allowed to stand at room temperature for five days to give block-like yellow crystals of (I) suitable for X-ray structural analysis.
6. Refinement
Crystal data, data collection and structure . All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.98 Å and N—H = 0.90–0.99 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 and restrained with O—H = 0.84 Å using DFIX and DANG commands (Sheldrick, 2015b).
details are summarized in Table 2
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Supporting information
CCDC reference: 1456673
https://doi.org/10.1107/S205698901600356X/wm5272sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901600356X/wm5272Isup2.hkl
Data collection: PAL BL2D-SMDC Program (Shin et al., 2016); cell
HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).[Cr(C10H24N4)(NH3)2][ZnCl4]Cl·H2O | Z = 4 |
Mr = 547 | F(000) = 1124 |
Triclinic, P1 | Dx = 1.640 Mg m−3 |
a = 9.3980 (19) Å | Synchrotron radiation, λ = 0.620 Å |
b = 14.876 (3) Å | Cell parameters from 76389 reflections |
c = 17.981 (4) Å | θ = 0.4–33.6° |
α = 66.03 (3)° | µ = 1.50 mm−1 |
β = 76.03 (3)° | T = 243 K |
γ = 78.74 (3)° | Block, yellow |
V = 2215.6 (10) Å3 | 0.11 × 0.08 × 0.04 mm |
ADSC Q210 CCD area-detector diffractometer | 11123 reflections with I > 2σ(I) |
Radiation source: PLSII 2D bending magnet | Rint = 0.029 |
ω scan | θmax = 26.0°, θmin = 1.1° |
Absorption correction: empirical (using intensity measurements) (HKL3000sm SCALEPACK; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.850, Tmax = 0.938 | k = −21→21 |
23883 measured reflections | l = −25→25 |
12905 independent reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1347P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
12905 reflections | Δρmax = 0.66 e Å−3 |
455 parameters | Δρmin = −0.76 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cr1A | 0.0000 | 0.5000 | 1.0000 | 0.00997 (6) | |
N1A | −0.05398 (13) | 0.36162 (9) | 1.01590 (7) | 0.0164 (2) | |
H1NA | 0.0293 | 0.3205 | 1.0125 | 0.025* | |
H2NA | −0.1031 | 0.3695 | 0.9761 | 0.025* | |
H3NA | −0.1111 | 0.3358 | 1.0658 | 0.025* | |
N2A | 0.17264 (13) | 0.42870 (9) | 1.06157 (7) | 0.0167 (2) | |
H1A | 0.1790 | 0.3582 | 1.0695 | 0.020* | |
N3A | 0.12143 (13) | 0.51146 (9) | 0.88534 (7) | 0.0157 (2) | |
H2A | 0.1219 | 0.4474 | 0.8806 | 0.019* | |
C1A | 0.12606 (17) | 0.43212 (12) | 1.14593 (9) | 0.0227 (3) | |
H1A1 | 0.1385 | 0.4971 | 1.1438 | 0.027* | |
H1A2 | 0.1870 | 0.3815 | 1.1838 | 0.027* | |
C2A | 0.32146 (16) | 0.46018 (12) | 1.01888 (10) | 0.0238 (3) | |
H2A1 | 0.3946 | 0.4181 | 1.0528 | 0.029* | |
H2A2 | 0.3230 | 0.5286 | 1.0127 | 0.029* | |
C3A | 0.36314 (16) | 0.45343 (13) | 0.93376 (11) | 0.0273 (3) | |
H3A1 | 0.4686 | 0.4605 | 0.9136 | 0.033* | |
H3A2 | 0.3483 | 0.3871 | 0.9400 | 0.033* | |
C4A | 0.27855 (16) | 0.52922 (12) | 0.86811 (9) | 0.0238 (3) | |
H4A1 | 0.2832 | 0.5956 | 0.8656 | 0.029* | |
H4A2 | 0.3257 | 0.5267 | 0.8140 | 0.029* | |
C5A | 0.03428 (17) | 0.58654 (12) | 0.82368 (8) | 0.0218 (3) | |
H5A1 | 0.0693 | 0.5810 | 0.7696 | 0.026* | |
H5A2 | 0.0457 | 0.6533 | 0.8177 | 0.026* | |
Cr2B | 0.5000 | 0.5000 | 0.5000 | 0.01185 (6) | |
N1B | 0.30918 (13) | 0.57334 (9) | 0.54783 (7) | 0.0188 (2) | |
H1NB | 0.2410 | 0.5307 | 0.5761 | 0.028* | |
H2NB | 0.2731 | 0.6239 | 0.5060 | 0.028* | |
H3NB | 0.3315 | 0.5969 | 0.5820 | 0.028* | |
N2B | 0.44033 (14) | 0.36582 (9) | 0.58615 (8) | 0.0204 (2) | |
H1B | 0.5253 | 0.3162 | 0.5812 | 0.024* | |
N3B | 0.62099 (14) | 0.51975 (10) | 0.57270 (8) | 0.0218 (2) | |
H2B | 0.7178 | 0.4803 | 0.5666 | 0.026* | |
C1B | 0.3178 (2) | 0.34242 (13) | 0.55956 (12) | 0.0317 (4) | |
H1B1 | 0.2242 | 0.3773 | 0.5768 | 0.038* | |
H1B2 | 0.3095 | 0.2712 | 0.5856 | 0.038* | |
C2B | 0.40555 (19) | 0.35503 (13) | 0.67422 (10) | 0.0299 (4) | |
H2B1 | 0.3851 | 0.2869 | 0.7092 | 0.036* | |
H2B2 | 0.3163 | 0.3990 | 0.6828 | 0.036* | |
C3B | 0.5303 (2) | 0.37936 (14) | 0.70072 (10) | 0.0318 (4) | |
H3B1 | 0.6206 | 0.3389 | 0.6873 | 0.038* | |
H3B2 | 0.5079 | 0.3591 | 0.7610 | 0.038* | |
C4B | 0.5622 (2) | 0.48701 (14) | 0.66301 (10) | 0.0300 (4) | |
H4B1 | 0.4712 | 0.5291 | 0.6725 | 0.036* | |
H4B2 | 0.6341 | 0.4950 | 0.6907 | 0.036* | |
C5B | 0.6501 (2) | 0.62542 (13) | 0.53436 (12) | 0.0315 (4) | |
H5B1 | 0.7347 | 0.6335 | 0.5531 | 0.038* | |
H5B2 | 0.5640 | 0.6667 | 0.5511 | 0.038* | |
Cr3C | 0.5000 | 1.0000 | 0.0000 | 0.01576 (6) | |
N1C | 0.54753 (15) | 0.84509 (9) | 0.04233 (8) | 0.0240 (3) | |
H1NC | 0.4628 | 0.8170 | 0.0595 | 0.036* | |
H2NC | 0.5966 | 0.8240 | 0.0847 | 0.036* | |
H3NC | 0.6036 | 0.8280 | 0.0009 | 0.036* | |
N2C | 0.63796 (15) | 1.01044 (11) | 0.06889 (8) | 0.0256 (3) | |
H1C | 0.6218 | 1.0801 | 0.0645 | 0.031* | |
N3C | 0.31688 (15) | 0.98526 (10) | 0.09225 (8) | 0.0243 (3) | |
H2C | 0.2794 | 1.0527 | 0.0913 | 0.029* | |
C1C | 0.79153 (19) | 0.99551 (16) | 0.02512 (12) | 0.0362 (4) | |
H1C1 | 0.8224 | 0.9246 | 0.0388 | 0.043* | |
H1C2 | 0.8590 | 1.0222 | 0.0429 | 0.043* | |
C2C | 0.6153 (2) | 0.94799 (15) | 0.15942 (11) | 0.0342 (4) | |
H2C1 | 0.6799 | 0.9657 | 0.1856 | 0.041* | |
H2C2 | 0.6432 | 0.8783 | 0.1669 | 0.041* | |
C3C | 0.4561 (2) | 0.96092 (15) | 0.20207 (10) | 0.0352 (4) | |
H3C1 | 0.4520 | 0.9271 | 0.2619 | 0.042* | |
H3C2 | 0.4278 | 1.0316 | 0.1908 | 0.042* | |
C4C | 0.3413 (2) | 0.92345 (13) | 0.17816 (10) | 0.0323 (4) | |
H4C1 | 0.3738 | 0.8550 | 0.1827 | 0.039* | |
H4C2 | 0.2479 | 0.9238 | 0.2168 | 0.039* | |
C5C | 0.20231 (19) | 0.95212 (15) | 0.06752 (12) | 0.0338 (4) | |
H5C1 | 0.1045 | 0.9676 | 0.0970 | 0.041* | |
H5C2 | 0.2198 | 0.8803 | 0.0822 | 0.041* | |
Cr4D | 0.0000 | 0.0000 | 0.5000 | 0.00919 (6) | |
N1D | 0.22787 (12) | −0.04570 (9) | 0.48598 (7) | 0.0160 (2) | |
H1ND | 0.2753 | −0.0002 | 0.4410 | 0.024* | |
H2ND | 0.2450 | −0.1042 | 0.4798 | 0.024* | |
H3ND | 0.2609 | −0.0523 | 0.5311 | 0.024* | |
N2D | 0.02941 (13) | 0.09509 (9) | 0.55052 (8) | 0.0177 (2) | |
H1D | −0.0667 | 0.1356 | 0.5558 | 0.021* | |
N3D | 0.02438 (12) | 0.10266 (9) | 0.38037 (7) | 0.0155 (2) | |
H2D | −0.0727 | 0.1423 | 0.3738 | 0.019* | |
C1D | 0.05317 (18) | 0.03371 (13) | 0.63680 (10) | 0.0255 (3) | |
H1D1 | 0.0337 | 0.0752 | 0.6695 | 0.031* | |
H1D2 | 0.1555 | 0.0031 | 0.6363 | 0.031* | |
C2D | 0.13974 (19) | 0.16666 (12) | 0.50160 (11) | 0.0284 (3) | |
H2D1 | 0.2385 | 0.1305 | 0.4978 | 0.034* | |
H2D2 | 0.1382 | 0.2108 | 0.5301 | 0.034* | |
C3D | 0.1080 (2) | 0.22836 (12) | 0.41438 (12) | 0.0320 (4) | |
H3D1 | 0.0048 | 0.2573 | 0.4193 | 0.038* | |
H3D2 | 0.1694 | 0.2832 | 0.3893 | 0.038* | |
C4D | 0.13418 (17) | 0.17441 (12) | 0.35548 (10) | 0.0264 (3) | |
H4D1 | 0.1281 | 0.2229 | 0.2994 | 0.032* | |
H4D2 | 0.2337 | 0.1390 | 0.3545 | 0.032* | |
C5D | 0.05122 (17) | 0.04541 (12) | 0.32576 (9) | 0.0238 (3) | |
H5D1 | 0.1536 | 0.0149 | 0.3213 | 0.029* | |
H5D2 | 0.0340 | 0.0896 | 0.2702 | 0.029* | |
Zn1E | 0.61151 (2) | 0.20650 (2) | 0.29082 (2) | 0.02403 (5) | |
Cl1E | 0.53804 (5) | 0.05903 (4) | 0.38072 (3) | 0.04285 (12) | |
Cl2E | 0.72540 (4) | 0.26657 (3) | 0.35901 (2) | 0.02630 (8) | |
Cl3E | 0.79024 (5) | 0.18205 (4) | 0.18756 (3) | 0.03439 (9) | |
Cl4E | 0.43263 (5) | 0.32125 (4) | 0.23927 (3) | 0.04760 (14) | |
Zn2F | 0.01806 (2) | 0.67654 (2) | 0.21094 (2) | 0.02221 (5) | |
Cl1F | −0.02844 (7) | 0.79302 (4) | 0.26421 (3) | 0.04689 (13) | |
Cl2F | 0.00187 (5) | 0.52354 (3) | 0.31592 (2) | 0.02954 (8) | |
Cl3F | −0.16681 (4) | 0.70070 (3) | 0.13702 (2) | 0.02651 (8) | |
Cl4F | 0.23650 (5) | 0.67718 (4) | 0.12345 (3) | 0.03785 (10) | |
Cl1W | 0.72406 (5) | 0.20867 (3) | 0.60004 (2) | 0.02949 (9) | |
Cl2W | 0.20883 (5) | 0.19663 (3) | 0.10707 (3) | 0.03019 (9) | |
O1W | 0.09042 (18) | 0.60251 (13) | 0.43830 (10) | 0.0463 (4) | |
H1O1 | 0.103 (3) | 0.6621 (9) | 0.4071 (13) | 0.056* | |
H2O1 | 0.055 (3) | 0.5784 (17) | 0.4128 (14) | 0.056* | |
O2W | 0.55603 (19) | 0.20704 (13) | 0.07745 (10) | 0.0473 (4) | |
H1O2 | 0.6248 (18) | 0.211 (2) | 0.0971 (15) | 0.057* | |
H2O2 | 0.4729 (15) | 0.215 (2) | 0.1061 (14) | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1A | 0.00887 (12) | 0.00962 (12) | 0.00992 (12) | −0.00051 (9) | −0.00151 (9) | −0.00252 (10) |
N1A | 0.0176 (5) | 0.0146 (5) | 0.0162 (5) | −0.0023 (4) | −0.0015 (4) | −0.0056 (4) |
N2A | 0.0132 (5) | 0.0156 (5) | 0.0202 (5) | 0.0000 (4) | −0.0071 (4) | −0.0043 (5) |
N3A | 0.0147 (5) | 0.0159 (5) | 0.0150 (5) | −0.0033 (4) | 0.0015 (4) | −0.0061 (4) |
C1A | 0.0261 (7) | 0.0253 (7) | 0.0168 (6) | −0.0044 (6) | −0.0111 (5) | −0.0031 (6) |
C2A | 0.0131 (6) | 0.0249 (7) | 0.0320 (8) | −0.0014 (5) | −0.0076 (5) | −0.0078 (6) |
C3A | 0.0127 (6) | 0.0316 (8) | 0.0361 (8) | 0.0008 (6) | 0.0006 (6) | −0.0155 (7) |
C4A | 0.0163 (6) | 0.0289 (8) | 0.0241 (7) | −0.0065 (5) | 0.0062 (5) | −0.0117 (6) |
C5A | 0.0280 (7) | 0.0240 (7) | 0.0113 (6) | −0.0066 (6) | −0.0044 (5) | −0.0021 (5) |
Cr2B | 0.01081 (12) | 0.01190 (13) | 0.01273 (13) | −0.00091 (10) | 0.00002 (10) | −0.00589 (11) |
N1B | 0.0173 (5) | 0.0188 (6) | 0.0183 (5) | 0.0006 (4) | 0.0005 (4) | −0.0081 (5) |
N2B | 0.0189 (6) | 0.0160 (6) | 0.0209 (6) | −0.0024 (4) | 0.0027 (4) | −0.0048 (5) |
N3B | 0.0206 (6) | 0.0259 (6) | 0.0243 (6) | −0.0011 (5) | −0.0058 (5) | −0.0147 (5) |
C1B | 0.0276 (8) | 0.0266 (8) | 0.0400 (9) | −0.0135 (6) | 0.0015 (7) | −0.0115 (7) |
C2B | 0.0306 (8) | 0.0269 (8) | 0.0184 (7) | 0.0007 (6) | 0.0054 (6) | −0.0018 (6) |
C3B | 0.0370 (9) | 0.0351 (9) | 0.0174 (7) | 0.0065 (7) | −0.0056 (6) | −0.0081 (7) |
C4B | 0.0353 (9) | 0.0363 (9) | 0.0230 (7) | 0.0062 (7) | −0.0104 (6) | −0.0175 (7) |
C5B | 0.0338 (9) | 0.0286 (8) | 0.0420 (10) | −0.0100 (7) | −0.0075 (7) | −0.0199 (8) |
Cr3C | 0.01463 (14) | 0.01256 (14) | 0.01522 (14) | 0.00175 (11) | −0.00218 (11) | −0.00211 (11) |
N1C | 0.0272 (6) | 0.0172 (6) | 0.0221 (6) | 0.0031 (5) | −0.0050 (5) | −0.0042 (5) |
N2C | 0.0237 (6) | 0.0261 (7) | 0.0250 (6) | −0.0005 (5) | −0.0076 (5) | −0.0069 (6) |
N3C | 0.0221 (6) | 0.0203 (6) | 0.0228 (6) | 0.0000 (5) | 0.0018 (5) | −0.0048 (5) |
C1C | 0.0201 (7) | 0.0428 (11) | 0.0411 (10) | 0.0004 (7) | −0.0091 (7) | −0.0111 (9) |
C2C | 0.0407 (10) | 0.0337 (9) | 0.0252 (8) | 0.0004 (8) | −0.0146 (7) | −0.0051 (7) |
C3C | 0.0482 (11) | 0.0321 (9) | 0.0191 (7) | −0.0011 (8) | −0.0037 (7) | −0.0061 (7) |
C4C | 0.0388 (9) | 0.0270 (8) | 0.0192 (7) | −0.0024 (7) | 0.0040 (6) | −0.0024 (6) |
C5C | 0.0198 (7) | 0.0373 (10) | 0.0372 (9) | −0.0077 (7) | 0.0014 (6) | −0.0087 (8) |
Cr4D | 0.00721 (11) | 0.00831 (12) | 0.01150 (12) | −0.00106 (9) | −0.00070 (9) | −0.00365 (10) |
N1D | 0.0103 (5) | 0.0159 (5) | 0.0192 (5) | −0.0007 (4) | −0.0014 (4) | −0.0050 (4) |
N2D | 0.0163 (5) | 0.0159 (5) | 0.0249 (6) | −0.0011 (4) | −0.0047 (4) | −0.0116 (5) |
N3D | 0.0123 (5) | 0.0140 (5) | 0.0156 (5) | −0.0012 (4) | −0.0018 (4) | −0.0015 (4) |
C1D | 0.0275 (7) | 0.0327 (8) | 0.0244 (7) | 0.0014 (6) | −0.0093 (6) | −0.0183 (7) |
C2D | 0.0268 (8) | 0.0224 (7) | 0.0427 (9) | −0.0117 (6) | −0.0071 (7) | −0.0145 (7) |
C3D | 0.0342 (9) | 0.0152 (7) | 0.0440 (10) | −0.0122 (6) | −0.0086 (7) | −0.0037 (7) |
C4D | 0.0209 (7) | 0.0220 (7) | 0.0255 (7) | −0.0094 (6) | −0.0011 (6) | 0.0032 (6) |
C5D | 0.0231 (7) | 0.0316 (8) | 0.0140 (6) | 0.0018 (6) | −0.0018 (5) | −0.0090 (6) |
Zn1E | 0.01617 (8) | 0.02918 (10) | 0.01970 (9) | −0.00577 (7) | −0.00537 (6) | 0.00052 (7) |
Cl1E | 0.02366 (19) | 0.0392 (2) | 0.0439 (3) | −0.01488 (18) | −0.00507 (17) | 0.0108 (2) |
Cl2E | 0.02669 (18) | 0.02502 (18) | 0.02753 (18) | 0.00389 (14) | −0.01067 (14) | −0.01004 (15) |
Cl3E | 0.0306 (2) | 0.0393 (2) | 0.02640 (19) | −0.00741 (17) | 0.00146 (15) | −0.00763 (18) |
Cl4E | 0.02096 (19) | 0.0463 (3) | 0.0538 (3) | −0.00297 (18) | −0.01940 (19) | 0.0098 (2) |
Zn2F | 0.02487 (9) | 0.02355 (9) | 0.02018 (9) | −0.00586 (7) | 0.00014 (6) | −0.01115 (7) |
Cl1F | 0.0642 (3) | 0.0419 (3) | 0.0483 (3) | −0.0180 (2) | 0.0050 (2) | −0.0338 (2) |
Cl2F | 0.0346 (2) | 0.02632 (19) | 0.02337 (17) | −0.00454 (15) | −0.00178 (15) | −0.00646 (15) |
Cl3F | 0.02952 (18) | 0.02757 (18) | 0.02467 (17) | 0.00596 (14) | −0.00829 (14) | −0.01429 (15) |
Cl4F | 0.0297 (2) | 0.0382 (2) | 0.0430 (2) | −0.01085 (17) | 0.01168 (17) | −0.0196 (2) |
Cl1W | 0.0332 (2) | 0.02203 (17) | 0.02665 (18) | 0.01129 (15) | −0.00334 (15) | −0.01016 (15) |
Cl2W | 0.0311 (2) | 0.01957 (17) | 0.0317 (2) | 0.00488 (14) | −0.00070 (15) | −0.00768 (15) |
O1W | 0.0420 (8) | 0.0565 (10) | 0.0491 (9) | 0.0026 (7) | −0.0231 (7) | −0.0239 (8) |
O2W | 0.0468 (9) | 0.0571 (10) | 0.0496 (9) | −0.0097 (8) | −0.0099 (7) | −0.0294 (8) |
Cr1A—N2Ai | 2.0553 (13) | N1C—H1NC | 0.9000 |
Cr1A—N2A | 2.0553 (13) | N1C—H2NC | 0.9000 |
Cr1A—N3Ai | 2.0582 (13) | N1C—H3NC | 0.9000 |
Cr1A—N3A | 2.0582 (13) | N2C—C1C | 1.490 (2) |
Cr1A—N1A | 2.1062 (13) | N2C—C2C | 1.496 (2) |
Cr1A—N1Ai | 2.1062 (13) | N2C—H1C | 0.9900 |
N1A—H1NA | 0.9000 | N3C—C5C | 1.489 (2) |
N1A—H2NA | 0.9000 | N3C—C4C | 1.490 (2) |
N1A—H3NA | 0.9000 | N3C—H2C | 0.9900 |
N2A—C2A | 1.4866 (19) | C1C—C5Ciii | 1.517 (3) |
N2A—C1A | 1.4928 (19) | C1C—H1C1 | 0.9800 |
N2A—H1A | 0.9900 | C1C—H1C2 | 0.9800 |
N3A—C4A | 1.4869 (19) | C2C—C3C | 1.522 (3) |
N3A—C5A | 1.491 (2) | C2C—H2C1 | 0.9800 |
N3A—H2A | 0.9900 | C2C—H2C2 | 0.9800 |
C1A—C5Ai | 1.513 (2) | C3C—C4C | 1.521 (3) |
C1A—H1A1 | 0.9800 | C3C—H3C1 | 0.9800 |
C1A—H1A2 | 0.9800 | C3C—H3C2 | 0.9800 |
C2A—C3A | 1.525 (2) | C4C—H4C1 | 0.9800 |
C2A—H2A1 | 0.9800 | C4C—H4C2 | 0.9800 |
C2A—H2A2 | 0.9800 | C5C—C1Ciii | 1.517 (3) |
C3A—C4A | 1.523 (2) | C5C—H5C1 | 0.9800 |
C3A—H3A1 | 0.9800 | C5C—H5C2 | 0.9800 |
C3A—H3A2 | 0.9800 | Cr4D—N2Div | 2.0544 (12) |
C4A—H4A1 | 0.9800 | Cr4D—N2D | 2.0544 (12) |
C4A—H4A2 | 0.9800 | Cr4D—N3D | 2.0593 (14) |
C5A—C1Ai | 1.513 (2) | Cr4D—N3Div | 2.0593 (14) |
C5A—H5A1 | 0.9800 | Cr4D—N1Div | 2.1029 (12) |
C5A—H5A2 | 0.9800 | Cr4D—N1D | 2.1029 (12) |
Cr2B—N2Bii | 2.0501 (15) | N1D—H1ND | 0.9000 |
Cr2B—N2B | 2.0502 (15) | N1D—H2ND | 0.9000 |
Cr2B—N3B | 2.0611 (13) | N1D—H3ND | 0.9000 |
Cr2B—N3Bii | 2.0611 (13) | N2D—C2D | 1.487 (2) |
Cr2B—N1B | 2.0976 (13) | N2D—C1D | 1.492 (2) |
Cr2B—N1Bii | 2.0977 (13) | N2D—H1D | 0.9900 |
N1B—H1NB | 0.9000 | N3D—C4D | 1.491 (2) |
N1B—H2NB | 0.9000 | N3D—C5D | 1.4932 (19) |
N1B—H3NB | 0.9000 | N3D—H2D | 0.9900 |
N2B—C2B | 1.485 (2) | C1D—C5Div | 1.513 (2) |
N2B—C1B | 1.494 (2) | C1D—H1D1 | 0.9800 |
N2B—H1B | 0.9900 | C1D—H1D2 | 0.9800 |
N3B—C4B | 1.486 (2) | C2D—C3D | 1.530 (3) |
N3B—C5B | 1.489 (2) | C2D—H2D1 | 0.9800 |
N3B—H2B | 0.9900 | C2D—H2D2 | 0.9800 |
C1B—C5Bii | 1.525 (3) | C3D—C4D | 1.521 (3) |
C1B—H1B1 | 0.9800 | C3D—H3D1 | 0.9800 |
C1B—H1B2 | 0.9800 | C3D—H3D2 | 0.9800 |
C2B—C3B | 1.519 (3) | C4D—H4D1 | 0.9800 |
C2B—H2B1 | 0.9800 | C4D—H4D2 | 0.9800 |
C2B—H2B2 | 0.9800 | C5D—C1Div | 1.513 (2) |
C3B—C4B | 1.524 (3) | C5D—H5D1 | 0.9800 |
C3B—H3B1 | 0.9800 | C5D—H5D2 | 0.9800 |
C3B—H3B2 | 0.9800 | Zn1E—Cl4E | 2.2238 (10) |
C4B—H4B1 | 0.9800 | Zn1E—Cl1E | 2.2523 (11) |
C4B—H4B2 | 0.9800 | Zn1E—Cl3E | 2.2817 (9) |
C5B—C1Bii | 1.525 (3) | Zn1E—Cl2E | 2.3118 (7) |
C5B—H5B1 | 0.9800 | Zn2F—Cl1F | 2.2275 (7) |
C5B—H5B2 | 0.9800 | Zn2F—Cl4F | 2.2640 (9) |
Cr3C—N3Ciii | 2.0579 (15) | Zn2F—Cl2F | 2.2960 (11) |
Cr3C—N3C | 2.0579 (15) | Zn2F—Cl3F | 2.3232 (8) |
Cr3C—N2Ciii | 2.0615 (15) | O1W—H1O1 | 0.848 (9) |
Cr3C—N2C | 2.0615 (15) | O1W—H2O1 | 0.836 (9) |
Cr3C—N1C | 2.1039 (14) | O2W—H1O2 | 0.832 (9) |
Cr3C—N1Ciii | 2.1039 (14) | O2W—H2O2 | 0.843 (9) |
N2Ai—Cr1A—N2A | 180.0 | N3C—Cr3C—N1C | 90.06 (6) |
N2Ai—Cr1A—N3Ai | 94.49 (5) | N2Ciii—Cr3C—N1C | 88.08 (6) |
N2A—Cr1A—N3Ai | 85.51 (5) | N2C—Cr3C—N1C | 91.92 (6) |
N2Ai—Cr1A—N3A | 85.51 (5) | N3Ciii—Cr3C—N1Ciii | 90.05 (6) |
N2A—Cr1A—N3A | 94.49 (5) | N3C—Cr3C—N1Ciii | 89.94 (6) |
N3Ai—Cr1A—N3A | 180.00 (4) | N2Ciii—Cr3C—N1Ciii | 91.92 (6) |
N2Ai—Cr1A—N1A | 90.76 (5) | N2C—Cr3C—N1Ciii | 88.08 (6) |
N2A—Cr1A—N1A | 89.24 (5) | N1C—Cr3C—N1Ciii | 180.00 (8) |
N3Ai—Cr1A—N1A | 91.07 (6) | Cr3C—N1C—H1NC | 109.5 |
N3A—Cr1A—N1A | 88.93 (6) | Cr3C—N1C—H2NC | 109.5 |
N2Ai—Cr1A—N1Ai | 89.24 (5) | H1NC—N1C—H2NC | 109.5 |
N2A—Cr1A—N1Ai | 90.76 (5) | Cr3C—N1C—H3NC | 109.5 |
N3Ai—Cr1A—N1Ai | 88.93 (6) | H1NC—N1C—H3NC | 109.5 |
N3A—Cr1A—N1Ai | 91.07 (6) | H2NC—N1C—H3NC | 109.5 |
N1A—Cr1A—N1Ai | 180.00 (6) | C1C—N2C—C2C | 113.16 (14) |
Cr1A—N1A—H1NA | 109.5 | C1C—N2C—Cr3C | 106.52 (11) |
Cr1A—N1A—H2NA | 109.5 | C2C—N2C—Cr3C | 117.72 (12) |
H1NA—N1A—H2NA | 109.5 | C1C—N2C—H1C | 106.2 |
Cr1A—N1A—H3NA | 109.5 | C2C—N2C—H1C | 106.2 |
H1NA—N1A—H3NA | 109.5 | Cr3C—N2C—H1C | 106.2 |
H2NA—N1A—H3NA | 109.5 | C5C—N3C—C4C | 113.35 (14) |
C2A—N2A—C1A | 114.29 (12) | C5C—N3C—Cr3C | 107.00 (10) |
C2A—N2A—Cr1A | 117.18 (9) | C4C—N3C—Cr3C | 116.36 (11) |
C1A—N2A—Cr1A | 106.44 (9) | C5C—N3C—H2C | 106.5 |
C2A—N2A—H1A | 106.0 | C4C—N3C—H2C | 106.5 |
C1A—N2A—H1A | 106.0 | Cr3C—N3C—H2C | 106.5 |
Cr1A—N2A—H1A | 106.0 | N2C—C1C—C5Ciii | 109.33 (14) |
C4A—N3A—C5A | 113.52 (12) | N2C—C1C—H1C1 | 109.8 |
C4A—N3A—Cr1A | 117.51 (9) | C5Ciii—C1C—H1C1 | 109.8 |
C5A—N3A—Cr1A | 106.14 (9) | N2C—C1C—H1C2 | 109.8 |
C4A—N3A—H2A | 106.3 | C5Ciii—C1C—H1C2 | 109.8 |
C5A—N3A—H2A | 106.3 | H1C1—C1C—H1C2 | 108.3 |
Cr1A—N3A—H2A | 106.3 | N2C—C2C—C3C | 112.24 (15) |
N2A—C1A—C5Ai | 108.42 (12) | N2C—C2C—H2C1 | 109.2 |
N2A—C1A—H1A1 | 110.0 | C3C—C2C—H2C1 | 109.2 |
C5Ai—C1A—H1A1 | 110.0 | N2C—C2C—H2C2 | 109.2 |
N2A—C1A—H1A2 | 110.0 | C3C—C2C—H2C2 | 109.2 |
C5Ai—C1A—H1A2 | 110.0 | H2C1—C2C—H2C2 | 107.9 |
H1A1—C1A—H1A2 | 108.4 | C4C—C3C—C2C | 116.90 (15) |
N2A—C2A—C3A | 111.60 (13) | C4C—C3C—H3C1 | 108.1 |
N2A—C2A—H2A1 | 109.3 | C2C—C3C—H3C1 | 108.1 |
C3A—C2A—H2A1 | 109.3 | C4C—C3C—H3C2 | 108.1 |
N2A—C2A—H2A2 | 109.3 | C2C—C3C—H3C2 | 108.1 |
C3A—C2A—H2A2 | 109.3 | H3C1—C3C—H3C2 | 107.3 |
H2A1—C2A—H2A2 | 108.0 | N3C—C4C—C3C | 111.92 (15) |
C4A—C3A—C2A | 115.86 (13) | N3C—C4C—H4C1 | 109.2 |
C4A—C3A—H3A1 | 108.3 | C3C—C4C—H4C1 | 109.2 |
C2A—C3A—H3A1 | 108.3 | N3C—C4C—H4C2 | 109.2 |
C4A—C3A—H3A2 | 108.3 | C3C—C4C—H4C2 | 109.2 |
C2A—C3A—H3A2 | 108.3 | H4C1—C4C—H4C2 | 107.9 |
H3A1—C3A—H3A2 | 107.4 | N3C—C5C—C1Ciii | 109.26 (15) |
N3A—C4A—C3A | 112.23 (13) | N3C—C5C—H5C1 | 109.8 |
N3A—C4A—H4A1 | 109.2 | C1Ciii—C5C—H5C1 | 109.8 |
C3A—C4A—H4A1 | 109.2 | N3C—C5C—H5C2 | 109.8 |
N3A—C4A—H4A2 | 109.2 | C1Ciii—C5C—H5C2 | 109.8 |
C3A—C4A—H4A2 | 109.2 | H5C1—C5C—H5C2 | 108.3 |
H4A1—C4A—H4A2 | 107.9 | N2Div—Cr4D—N2D | 180.0 |
N3A—C5A—C1Ai | 108.15 (12) | N2Div—Cr4D—N3D | 85.25 (5) |
N3A—C5A—H5A1 | 110.1 | N2D—Cr4D—N3D | 94.75 (5) |
C1Ai—C5A—H5A1 | 110.1 | N2Div—Cr4D—N3Div | 94.76 (5) |
N3A—C5A—H5A2 | 110.1 | N2D—Cr4D—N3Div | 85.24 (5) |
C1Ai—C5A—H5A2 | 110.1 | N3D—Cr4D—N3Div | 180.0 |
H5A1—C5A—H5A2 | 108.4 | N2Div—Cr4D—N1Div | 89.83 (5) |
N2Bii—Cr2B—N2B | 180.0 | N2D—Cr4D—N1Div | 90.17 (5) |
N2Bii—Cr2B—N3B | 85.91 (6) | N3D—Cr4D—N1Div | 88.87 (6) |
N2B—Cr2B—N3B | 94.09 (6) | N3Div—Cr4D—N1Div | 91.13 (6) |
N2Bii—Cr2B—N3Bii | 94.09 (6) | N2Div—Cr4D—N1D | 90.17 (5) |
N2B—Cr2B—N3Bii | 85.91 (6) | N2D—Cr4D—N1D | 89.83 (5) |
N3B—Cr2B—N3Bii | 180.00 (7) | N3D—Cr4D—N1D | 91.13 (6) |
N2Bii—Cr2B—N1B | 89.22 (6) | N3Div—Cr4D—N1D | 88.87 (6) |
N2B—Cr2B—N1B | 90.78 (6) | N1Div—Cr4D—N1D | 180.0 |
N3B—Cr2B—N1B | 91.36 (5) | Cr4D—N1D—H1ND | 109.5 |
N3Bii—Cr2B—N1B | 88.64 (5) | Cr4D—N1D—H2ND | 109.5 |
N2Bii—Cr2B—N1Bii | 90.78 (6) | H1ND—N1D—H2ND | 109.5 |
N2B—Cr2B—N1Bii | 89.22 (6) | Cr4D—N1D—H3ND | 109.5 |
N3B—Cr2B—N1Bii | 88.64 (5) | H1ND—N1D—H3ND | 109.5 |
N3Bii—Cr2B—N1Bii | 91.36 (5) | H2ND—N1D—H3ND | 109.5 |
N1B—Cr2B—N1Bii | 180.00 (6) | C2D—N2D—C1D | 114.07 (12) |
Cr2B—N1B—H1NB | 109.5 | C2D—N2D—Cr4D | 117.13 (10) |
Cr2B—N1B—H2NB | 109.5 | C1D—N2D—Cr4D | 107.05 (9) |
H1NB—N1B—H2NB | 109.5 | C2D—N2D—H1D | 105.9 |
Cr2B—N1B—H3NB | 109.5 | C1D—N2D—H1D | 105.9 |
H1NB—N1B—H3NB | 109.5 | Cr4D—N2D—H1D | 105.9 |
H2NB—N1B—H3NB | 109.5 | C4D—N3D—C5D | 113.03 (12) |
C2B—N2B—C1B | 112.86 (13) | C4D—N3D—Cr4D | 117.41 (10) |
C2B—N2B—Cr2B | 116.96 (11) | C5D—N3D—Cr4D | 106.16 (9) |
C1B—N2B—Cr2B | 106.88 (10) | C4D—N3D—H2D | 106.5 |
C2B—N2B—H1B | 106.5 | C5D—N3D—H2D | 106.5 |
C1B—N2B—H1B | 106.5 | Cr4D—N3D—H2D | 106.5 |
Cr2B—N2B—H1B | 106.5 | N2D—C1D—C5Div | 108.07 (12) |
C4B—N3B—C5B | 112.83 (13) | N2D—C1D—H1D1 | 110.1 |
C4B—N3B—Cr2B | 117.59 (11) | C5Div—C1D—H1D1 | 110.1 |
C5B—N3B—Cr2B | 106.77 (10) | N2D—C1D—H1D2 | 110.1 |
C4B—N3B—H2B | 106.3 | C5Div—C1D—H1D2 | 110.1 |
C5B—N3B—H2B | 106.3 | H1D1—C1D—H1D2 | 108.4 |
Cr2B—N3B—H2B | 106.3 | N2D—C2D—C3D | 111.55 (13) |
N2B—C1B—C5Bii | 109.12 (14) | N2D—C2D—H2D1 | 109.3 |
N2B—C1B—H1B1 | 109.9 | C3D—C2D—H2D1 | 109.3 |
C5Bii—C1B—H1B1 | 109.9 | N2D—C2D—H2D2 | 109.3 |
N2B—C1B—H1B2 | 109.9 | C3D—C2D—H2D2 | 109.3 |
C5Bii—C1B—H1B2 | 109.9 | H2D1—C2D—H2D2 | 108.0 |
H1B1—C1B—H1B2 | 108.3 | C4D—C3D—C2D | 116.59 (14) |
N2B—C2B—C3B | 112.58 (14) | C4D—C3D—H3D1 | 108.1 |
N2B—C2B—H2B1 | 109.1 | C2D—C3D—H3D1 | 108.1 |
C3B—C2B—H2B1 | 109.1 | C4D—C3D—H3D2 | 108.1 |
N2B—C2B—H2B2 | 109.1 | C2D—C3D—H3D2 | 108.1 |
C3B—C2B—H2B2 | 109.1 | H3D1—C3D—H3D2 | 107.3 |
H2B1—C2B—H2B2 | 107.8 | N3D—C4D—C3D | 111.82 (13) |
C2B—C3B—C4B | 116.95 (15) | N3D—C4D—H4D1 | 109.3 |
C2B—C3B—H3B1 | 108.1 | C3D—C4D—H4D1 | 109.3 |
C4B—C3B—H3B1 | 108.1 | N3D—C4D—H4D2 | 109.3 |
C2B—C3B—H3B2 | 108.1 | C3D—C4D—H4D2 | 109.3 |
C4B—C3B—H3B2 | 108.1 | H4D1—C4D—H4D2 | 107.9 |
H3B1—C3B—H3B2 | 107.3 | N3D—C5D—C1Div | 108.31 (12) |
N3B—C4B—C3B | 112.03 (13) | N3D—C5D—H5D1 | 110.0 |
N3B—C4B—H4B1 | 109.2 | C1Div—C5D—H5D1 | 110.0 |
C3B—C4B—H4B1 | 109.2 | N3D—C5D—H5D2 | 110.0 |
N3B—C4B—H4B2 | 109.2 | C1Div—C5D—H5D2 | 110.0 |
C3B—C4B—H4B2 | 109.2 | H5D1—C5D—H5D2 | 108.4 |
H4B1—C4B—H4B2 | 107.9 | Cl4E—Zn1E—Cl1E | 115.38 (3) |
N3B—C5B—C1Bii | 109.08 (13) | Cl4E—Zn1E—Cl3E | 110.99 (3) |
N3B—C5B—H5B1 | 109.9 | Cl1E—Zn1E—Cl3E | 108.75 (4) |
C1Bii—C5B—H5B1 | 109.9 | Cl4E—Zn1E—Cl2E | 107.79 (3) |
N3B—C5B—H5B2 | 109.9 | Cl1E—Zn1E—Cl2E | 107.77 (3) |
C1Bii—C5B—H5B2 | 109.9 | Cl3E—Zn1E—Cl2E | 105.67 (3) |
H5B1—C5B—H5B2 | 108.3 | Cl1F—Zn2F—Cl4F | 115.32 (3) |
N3Ciii—Cr3C—N3C | 180.00 (6) | Cl1F—Zn2F—Cl2F | 109.63 (3) |
N3Ciii—Cr3C—N2Ciii | 94.32 (6) | Cl4F—Zn2F—Cl2F | 109.79 (4) |
N3C—Cr3C—N2Ciii | 85.68 (6) | Cl1F—Zn2F—Cl3F | 107.62 (3) |
N3Ciii—Cr3C—N2C | 85.68 (6) | Cl4F—Zn2F—Cl3F | 107.31 (2) |
N3C—Cr3C—N2C | 94.32 (6) | Cl2F—Zn2F—Cl3F | 106.77 (4) |
N2Ciii—Cr3C—N2C | 180.0 | H1O1—O1W—H2O1 | 107.9 (19) |
N3Ciii—Cr3C—N1C | 89.94 (6) | H1O2—O2W—H2O2 | 112.1 (19) |
C2A—N2A—C1A—C5Ai | 171.57 (12) | C2C—N2C—C1C—C5Ciii | 170.49 (16) |
Cr1A—N2A—C1A—C5Ai | 40.59 (14) | Cr3C—N2C—C1C—C5Ciii | 39.61 (18) |
C1A—N2A—C2A—C3A | 179.11 (12) | C1C—N2C—C2C—C3C | −177.36 (16) |
Cr1A—N2A—C2A—C3A | −55.38 (15) | Cr3C—N2C—C2C—C3C | −52.33 (19) |
N2A—C2A—C3A—C4A | 70.45 (18) | N2C—C2C—C3C—C4C | 67.1 (2) |
C5A—N3A—C4A—C3A | 178.01 (12) | C5C—N3C—C4C—C3C | −178.55 (14) |
Cr1A—N3A—C4A—C3A | 53.37 (15) | Cr3C—N3C—C4C—C3C | 56.74 (17) |
C2A—C3A—C4A—N3A | −69.39 (18) | C2C—C3C—C4C—N3C | −69.9 (2) |
C4A—N3A—C5A—C1Ai | −172.82 (12) | C4C—N3C—C5C—C1Ciii | −167.98 (14) |
Cr1A—N3A—C5A—C1Ai | −42.24 (13) | Cr3C—N3C—C5C—C1Ciii | −38.36 (16) |
C2B—N2B—C1B—C5Bii | 169.01 (14) | C2D—N2D—C1D—C5Div | −171.39 (12) |
Cr2B—N2B—C1B—C5Bii | 39.06 (15) | Cr4D—N2D—C1D—C5Div | −40.14 (13) |
C1B—N2B—C2B—C3B | −179.75 (14) | C1D—N2D—C2D—C3D | −179.09 (13) |
Cr2B—N2B—C2B—C3B | −55.15 (16) | Cr4D—N2D—C2D—C3D | 54.77 (16) |
N2B—C2B—C3B—C4B | 68.20 (19) | N2D—C2D—C3D—C4D | −70.12 (19) |
C5B—N3B—C4B—C3B | 178.83 (14) | C5D—N3D—C4D—C3D | −177.52 (13) |
Cr2B—N3B—C4B—C3B | 53.86 (17) | Cr4D—N3D—C4D—C3D | −53.38 (16) |
C2B—C3B—C4B—N3B | −67.16 (19) | C2D—C3D—C4D—N3D | 69.25 (19) |
C4B—N3B—C5B—C1Bii | −169.58 (14) | C4D—N3D—C5D—C1Div | 172.59 (12) |
Cr2B—N3B—C5B—C1Bii | −38.92 (16) | Cr4D—N3D—C5D—C1Div | 42.50 (13) |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1NA···Cl3Fv | 0.90 | 2.80 | 3.3602 (16) | 121 |
N1A—H1NA···Cl2Wvi | 0.90 | 2.60 | 3.3363 (18) | 140 |
N1A—H3NA···Cl3Evii | 0.90 | 2.58 | 3.384 (2) | 149 |
N2A—H1A···Cl2Wvi | 0.99 | 2.20 | 3.1754 (15) | 170 |
N3A—H2A···Cl3Fv | 0.99 | 2.30 | 3.2752 (14) | 170 |
C1A—H1A2···Cl4Evi | 0.98 | 2.59 | 3.4739 (19) | 150 |
N1B—H2NB···Cl1Wii | 0.90 | 2.45 | 3.2683 (19) | 152 |
N1B—H2NB···O1W | 0.90 | 2.46 | 3.034 (2) | 122 |
N1B—H3NB···Cl2Eii | 0.90 | 2.57 | 3.3556 (15) | 147 |
N2B—H1B···Cl1W | 0.99 | 2.20 | 3.1704 (17) | 165 |
N3B—H2B···O1Wii | 0.99 | 1.98 | 2.968 (2) | 177 |
N1C—H2NC···Cl3Fviii | 0.90 | 2.68 | 3.4211 (19) | 140 |
N1C—H3NC···Cl2Wix | 0.90 | 2.38 | 3.2673 (17) | 167 |
N1C—H3NC···O2Wix | 0.90 | 2.54 | 2.975 (2) | 111 |
N2C—H1C···O2Wx | 0.99 | 1.96 | 2.932 (2) | 167 |
N3C—H2C···Cl2Wx | 0.99 | 2.23 | 3.2082 (16) | 171 |
C5C—H5C2···Cl4F | 0.98 | 2.79 | 3.761 (2) | 174 |
N1D—H2ND···Cl1Wxi | 0.90 | 2.45 | 3.2796 (15) | 154 |
N1D—H3ND···Cl1Exi | 0.90 | 2.71 | 3.5516 (16) | 156 |
N2D—H1D···Cl1Wxii | 0.99 | 2.19 | 3.1589 (16) | 166 |
N3D—H2D···Cl2Exii | 0.99 | 2.36 | 3.3276 (17) | 166 |
C1D—H1D1···Cl1Fv | 0.98 | 2.66 | 3.6278 (17) | 168 |
C1D—H1D2···Cl1Exi | 0.98 | 2.83 | 3.803 (2) | 172 |
O1W—H1O1···Cl1Wii | 0.85 (1) | 2.70 (2) | 3.341 (2) | 134 (2) |
O1W—H2O1···Cl2F | 0.84 (1) | 2.39 (1) | 3.2066 (17) | 167 (2) |
O2W—H1O2···Cl3E | 0.83 (1) | 2.37 (1) | 3.1763 (19) | 162 (2) |
O2W—H2O2···Cl2W | 0.84 (1) | 2.55 (2) | 3.2009 (19) | 135 (2) |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x, y, z+1; (vii) x−1, y, z+1; (viii) x+1, y, z; (ix) −x+1, −y+1, −z; (x) x, y+1, z; (xi) −x+1, −y, −z+1; (xii) x−1, y, z. |
Acknowledgements
This work was supported by a grant from 2016 Research Funds of Andong National University. The X-ray crystallography experiment at the PLS-II BL2D-SMC beamline was supported in part by MSIP and POSTECH.
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