Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024853/at2299sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024853/at2299Isup2.hkl |
CCDC reference: 650698
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.029
- wR factor = 0.069
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd1 (2) 2.14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
2-(Methylsulfanyl)diazenyl-4-cholorobenzene was prepared by coupling 2-(methylsulfanyl)aniline with 4-nitrosochlorobenzene. The ligand thus obtained was reacted with Na2PdCl4 following a reported method (Mahapatra et al., 1986). The product was purified by coloumn chromatographic technique using silica gel column and methanol and dichloromethane (1: 9 v/v) mixture as eluant. The solvent was evaporated in vacuum to obtain the pure product (yield: 83.9%). Suitable crystals of (I) were grown from a dichloromethane-hexane solution by slow evaporation.
H atoms were included at calculated positions as riding atoms with C–H set to 0.93 Å for (aromatic) and 0.96 Å for (CH3) H atoms, with Uiso(H) = 1.2Ueq(C) (1.5Ueq for methyl group).
Cyclopalladated compounds have numerous applications (Dupont et al., 2005) in organic synthesis, catalysis, photochemistry and metallomesogen chemistry. Although a number of cyclometallated complexes of palladium (Omae, 2004 & Neogi et al., 2006) have been reported in literature, report of palladium complexes with sulfur as an auxiliary donor is relatively sparse (Pal et al., 1992). Against this background, we report here the crystal structure of (I).
The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The palladium atom along with donor set of four atoms lie in an almost plane. Selected bond lengths and bond angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N?N bond length is typical of other cyclopalladated azoarenes (Neogi et al., 2006), unlike that of other free azoarenes containing thioether moiety (Das et al., 2006). The metal carbon bond length, 1.977 (3) Å, is higher than the reported values of other ortho-palladated azoarenes (Bagchi & Bandyopadhyay, 2007). The molecules are found to dimerize through a nonbonded S···S interaction; having S···Si [symmetry code: (i) 1 - x, -y, 1 - z] distance of 3.5162 (17) Å (Chattopadhyay et al., 1991) (Fig. 3). Four inter molecular π—π interactions (Kubo et al., 2005 & Bagchi & Bandyopadhyay, 2007) arrange the molecules in anti parallel fashion (Fig. 4). The Cg3—Cg4ii, Cg3—Cg4iii, Cg4—Cg3ii, Cg4—Cg3iii, [symmetry codes: (ii) -x, 1 - y, 1 - z; (iii) 1 - x, 1 - y, 1-z. Cg3 and Cg4 are the centroids of C1—C6 and C7—C12 rings, respectively.] distances are 3.808 (2), 3.623 (2), 3.808 (2) and 3.623 (2) Å; the corresponding perpendicular distances are 3.462, 3.454, 3.402 and 3.402 Å with slippages of 3.402, 3.402, 3.462 and 3.454 Å, respectively.
For related literature, see: Bagchi & Bandyopadhyay (2007); Chattopadhyay et al. (1991); Das et al. (2006); Dupont et al. (2005); Kubo et al. (2005); Mahapatra et al. (1986); Neogi et al. (2006); Omae (2004); Pal et al. (1992).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
[Pd(C13H10ClN2S)Cl] | Z = 2 |
Mr = 403.59 | F(000) = 396 |
Triclinic, P1 | Dx = 1.952 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.413 (2) Å | Cell parameters from 3745 reflections |
b = 8.768 (3) Å | θ = 2.4–28.0° |
c = 11.051 (3) Å | µ = 1.88 mm−1 |
α = 105.330 (4)° | T = 298 K |
β = 92.875 (5)° | Block, red |
γ = 95.995 (5)° | 0.43 × 0.28 × 0.19 mm |
V = 686.7 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 2416 independent reflections |
Radiation source: fine-focus sealed tube | 2308 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.538, Tmax = 0.701 | k = −10→10 |
6579 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0218P)2 + 0.4766P] where P = (Fo2 + 2Fc2)/3 |
2416 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
[Pd(C13H10ClN2S)Cl] | γ = 95.995 (5)° |
Mr = 403.59 | V = 686.7 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.413 (2) Å | Mo Kα radiation |
b = 8.768 (3) Å | µ = 1.88 mm−1 |
c = 11.051 (3) Å | T = 298 K |
α = 105.330 (4)° | 0.43 × 0.28 × 0.19 mm |
β = 92.875 (5)° |
Bruker SMART CCD area-detector diffractometer | 2416 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2308 reflections with I > 2σ(I) |
Tmin = 0.538, Tmax = 0.701 | Rint = 0.035 |
6579 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.37 e Å−3 |
2416 reflections | Δρmin = −0.43 e Å−3 |
173 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C8 | 0.1472 (5) | 0.7783 (4) | 0.6873 (4) | 0.0399 (8) | |
H8 | 0.1402 | 0.8514 | 0.6402 | 0.048* | |
C13 | 0.2318 (6) | −0.0523 (4) | 0.3667 (4) | 0.0547 (10) | |
H13A | 0.2241 | −0.1112 | 0.4286 | 0.082* | |
H13B | 0.2717 | −0.1173 | 0.2909 | 0.082* | |
H13C | 0.1143 | −0.0227 | 0.3490 | 0.082* | |
C4 | 0.3860 (5) | 0.2481 (5) | 0.0990 (4) | 0.0524 (10) | |
H4 | 0.4078 | 0.2022 | 0.0159 | 0.063* | |
C12 | 0.2017 (4) | 0.5121 (4) | 0.6990 (3) | 0.0324 (7) | |
C11 | 0.1687 (5) | 0.5551 (4) | 0.8249 (3) | 0.0373 (8) | |
H11 | 0.1743 | 0.4828 | 0.8728 | 0.045* | |
Pd1 | 0.28010 (3) | 0.31568 (3) | 0.59178 (2) | 0.03148 (10) | |
S | 0.39237 (12) | 0.12483 (10) | 0.42611 (8) | 0.0373 (2) | |
Cl1 | 0.29394 (16) | 0.18486 (11) | 0.74538 (9) | 0.0551 (3) | |
Cl2 | 0.08874 (16) | 0.76042 (13) | 1.03770 (9) | 0.0599 (3) | |
N1 | 0.2693 (4) | 0.4451 (3) | 0.4709 (3) | 0.0317 (6) | |
N2 | 0.2272 (4) | 0.5860 (3) | 0.5041 (3) | 0.0352 (6) | |
C1 | 0.3113 (4) | 0.3831 (4) | 0.3433 (3) | 0.0326 (7) | |
C9 | 0.1155 (5) | 0.8202 (4) | 0.8127 (4) | 0.0417 (8) | |
H9 | 0.0869 | 0.9214 | 0.8517 | 0.050* | |
C10 | 0.1271 (5) | 0.7082 (4) | 0.8789 (3) | 0.0396 (8) | |
C6 | 0.3623 (4) | 0.2299 (4) | 0.3102 (3) | 0.0344 (7) | |
C7 | 0.1897 (4) | 0.6260 (4) | 0.6309 (3) | 0.0333 (7) | |
C2 | 0.3014 (5) | 0.4691 (4) | 0.2552 (3) | 0.0412 (8) | |
H2 | 0.2690 | 0.5719 | 0.2779 | 0.049* | |
C5 | 0.4002 (5) | 0.1628 (5) | 0.1866 (3) | 0.0451 (9) | |
H5 | 0.4348 | 0.0608 | 0.1633 | 0.054* | |
C3 | 0.3400 (5) | 0.4010 (5) | 0.1337 (4) | 0.0494 (10) | |
H3 | 0.3349 | 0.4587 | 0.0744 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C8 | 0.043 (2) | 0.0319 (18) | 0.047 (2) | 0.0092 (15) | 0.0064 (16) | 0.0120 (16) |
C13 | 0.069 (3) | 0.036 (2) | 0.054 (3) | −0.0035 (19) | −0.008 (2) | 0.0078 (18) |
C4 | 0.053 (2) | 0.072 (3) | 0.0292 (19) | 0.004 (2) | 0.0054 (17) | 0.0081 (19) |
C12 | 0.0320 (17) | 0.0282 (16) | 0.0347 (18) | 0.0041 (13) | 0.0034 (14) | 0.0045 (14) |
C11 | 0.044 (2) | 0.0313 (18) | 0.0349 (19) | 0.0031 (15) | 0.0039 (15) | 0.0058 (15) |
Pd1 | 0.04049 (17) | 0.02465 (15) | 0.02860 (16) | 0.00572 (10) | 0.00310 (11) | 0.00526 (10) |
S | 0.0452 (5) | 0.0335 (4) | 0.0320 (5) | 0.0116 (4) | 0.0017 (4) | 0.0046 (4) |
Cl1 | 0.0936 (8) | 0.0372 (5) | 0.0413 (5) | 0.0175 (5) | 0.0143 (5) | 0.0174 (4) |
Cl2 | 0.0818 (7) | 0.0539 (6) | 0.0375 (5) | 0.0141 (5) | 0.0122 (5) | −0.0027 (4) |
N1 | 0.0318 (15) | 0.0316 (15) | 0.0318 (15) | 0.0033 (11) | 0.0015 (11) | 0.0094 (12) |
N2 | 0.0383 (16) | 0.0286 (14) | 0.0390 (16) | 0.0056 (12) | 0.0035 (12) | 0.0090 (12) |
C1 | 0.0292 (17) | 0.0379 (18) | 0.0287 (17) | 0.0019 (14) | 0.0013 (13) | 0.0065 (14) |
C9 | 0.040 (2) | 0.0311 (18) | 0.051 (2) | 0.0086 (15) | 0.0070 (17) | 0.0035 (16) |
C10 | 0.0392 (19) | 0.0378 (19) | 0.0348 (19) | 0.0017 (15) | 0.0077 (15) | −0.0018 (15) |
C6 | 0.0315 (17) | 0.0387 (18) | 0.0316 (18) | 0.0051 (14) | 0.0024 (14) | 0.0067 (15) |
C7 | 0.0335 (18) | 0.0297 (17) | 0.0350 (18) | 0.0043 (13) | 0.0044 (14) | 0.0055 (14) |
C2 | 0.041 (2) | 0.044 (2) | 0.041 (2) | 0.0051 (16) | 0.0013 (16) | 0.0153 (17) |
C5 | 0.046 (2) | 0.047 (2) | 0.040 (2) | 0.0095 (17) | 0.0063 (16) | 0.0044 (17) |
C3 | 0.048 (2) | 0.065 (3) | 0.039 (2) | 0.0063 (19) | 0.0028 (17) | 0.020 (2) |
C8—C9 | 1.376 (5) | Pd1—Cl1 | 2.2900 (11) |
C8—C7 | 1.392 (5) | Pd1—S | 2.3810 (10) |
C8—H8 | 0.9300 | S—C6 | 1.783 (3) |
C13—S | 1.805 (4) | Cl2—C10 | 1.739 (4) |
C13—H13A | 0.9600 | N1—N2 | 1.270 (4) |
C13—H13B | 0.9600 | N1—C1 | 1.433 (4) |
C13—H13C | 0.9600 | N2—C7 | 1.401 (4) |
C4—C5 | 1.377 (6) | C1—C2 | 1.384 (5) |
C4—C3 | 1.378 (6) | C1—C6 | 1.393 (5) |
C4—H4 | 0.9300 | C9—C10 | 1.377 (5) |
C12—C11 | 1.383 (5) | C9—H9 | 0.9300 |
C12—C7 | 1.407 (5) | C6—C5 | 1.392 (5) |
C12—Pd1 | 1.977 (3) | C2—C3 | 1.375 (5) |
C11—C10 | 1.391 (5) | C2—H2 | 0.9300 |
C11—H11 | 0.9300 | C5—H5 | 0.9300 |
Pd1—N1 | 1.972 (3) | C3—H3 | 0.9300 |
C9—C8—C7 | 119.8 (3) | N2—N1—Pd1 | 121.0 (2) |
C9—C8—H8 | 120.1 | C1—N1—Pd1 | 120.8 (2) |
C7—C8—H8 | 120.1 | N1—N2—C7 | 110.3 (3) |
S—C13—H13A | 109.5 | C2—C1—C6 | 120.5 (3) |
S—C13—H13B | 109.5 | C2—C1—N1 | 122.4 (3) |
H13A—C13—H13B | 109.5 | C6—C1—N1 | 117.1 (3) |
S—C13—H13C | 109.5 | C8—C9—C10 | 118.2 (3) |
H13A—C13—H13C | 109.5 | C8—C9—H9 | 120.9 |
H13B—C13—H13C | 109.5 | C10—C9—H9 | 120.9 |
C5—C4—C3 | 120.5 (4) | C9—C10—C11 | 123.2 (3) |
C5—C4—H4 | 119.8 | C9—C10—Cl2 | 118.6 (3) |
C3—C4—H4 | 119.8 | C11—C10—Cl2 | 118.2 (3) |
C11—C12—C7 | 118.0 (3) | C5—C6—C1 | 119.3 (3) |
C11—C12—Pd1 | 131.4 (3) | C5—C6—S | 119.9 (3) |
C7—C12—Pd1 | 110.4 (2) | C1—C6—S | 120.6 (3) |
C12—C11—C10 | 119.0 (3) | C8—C7—N2 | 119.4 (3) |
C12—C11—H11 | 120.5 | C8—C7—C12 | 121.7 (3) |
C10—C11—H11 | 120.5 | N2—C7—C12 | 118.9 (3) |
N1—Pd1—C12 | 79.36 (13) | C3—C2—C1 | 119.3 (4) |
N1—Pd1—Cl1 | 175.20 (8) | C3—C2—H2 | 120.3 |
C12—Pd1—Cl1 | 96.12 (10) | C1—C2—H2 | 120.3 |
N1—Pd1—S | 85.42 (9) | C4—C5—C6 | 119.7 (4) |
C12—Pd1—S | 164.33 (10) | C4—C5—H5 | 120.2 |
Cl1—Pd1—S | 98.98 (4) | C6—C5—H5 | 120.2 |
C6—S—C13 | 102.51 (17) | C2—C3—C4 | 120.7 (4) |
C6—S—Pd1 | 95.55 (11) | C2—C3—H3 | 119.7 |
C13—S—Pd1 | 112.06 (15) | C4—C3—H3 | 119.7 |
N2—N1—C1 | 118.2 (3) | ||
C7—C12—C11—C10 | −0.6 (5) | C8—C9—C10—Cl2 | 179.6 (3) |
Pd1—C12—C11—C10 | 175.3 (2) | C12—C11—C10—C9 | 0.5 (5) |
C11—C12—Pd1—N1 | −177.7 (3) | C12—C11—C10—Cl2 | −179.3 (2) |
C7—C12—Pd1—N1 | −1.7 (2) | C2—C1—C6—C5 | −1.2 (5) |
C11—C12—Pd1—Cl1 | 0.6 (3) | N1—C1—C6—C5 | 178.4 (3) |
C7—C12—Pd1—Cl1 | 176.7 (2) | C2—C1—C6—S | 175.1 (3) |
C11—C12—Pd1—S | −163.8 (2) | N1—C1—C6—S | −5.3 (4) |
C7—C12—Pd1—S | 12.3 (5) | C13—S—C6—C5 | −62.4 (3) |
N1—Pd1—S—C6 | −5.55 (13) | Pd1—S—C6—C5 | −176.4 (3) |
C12—Pd1—S—C6 | −19.3 (4) | C13—S—C6—C1 | 121.4 (3) |
Cl1—Pd1—S—C6 | 176.39 (11) | Pd1—S—C6—C1 | 7.3 (3) |
N1—Pd1—S—C13 | −111.46 (17) | C9—C8—C7—N2 | −178.1 (3) |
C12—Pd1—S—C13 | −125.2 (4) | C9—C8—C7—C12 | 0.0 (5) |
Cl1—Pd1—S—C13 | 70.47 (15) | N1—N2—C7—C8 | 177.6 (3) |
C12—Pd1—N1—N2 | 1.7 (2) | N1—N2—C7—C12 | −0.5 (4) |
S—Pd1—N1—N2 | −174.5 (2) | C11—C12—C7—C8 | 0.3 (5) |
C12—Pd1—N1—C1 | −179.1 (2) | Pd1—C12—C7—C8 | −176.3 (3) |
S—Pd1—N1—C1 | 4.6 (2) | C11—C12—C7—N2 | 178.4 (3) |
C1—N1—N2—C7 | 179.7 (3) | Pd1—C12—C7—N2 | 1.7 (4) |
Pd1—N1—N2—C7 | −1.2 (3) | C6—C1—C2—C3 | 0.9 (5) |
N2—N1—C1—C2 | −2.2 (5) | N1—C1—C2—C3 | −178.7 (3) |
Pd1—N1—C1—C2 | 178.6 (2) | C3—C4—C5—C6 | 1.9 (6) |
N2—N1—C1—C6 | 178.2 (3) | C1—C6—C5—C4 | −0.3 (5) |
Pd1—N1—C1—C6 | −1.0 (4) | S—C6—C5—C4 | −176.5 (3) |
C7—C8—C9—C10 | 0.0 (5) | C1—C2—C3—C4 | 0.7 (6) |
C8—C9—C10—C11 | −0.2 (5) | C5—C4—C3—C2 | −2.2 (6) |
Experimental details
Crystal data | |
Chemical formula | [Pd(C13H10ClN2S)Cl] |
Mr | 403.59 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.413 (2), 8.768 (3), 11.051 (3) |
α, β, γ (°) | 105.330 (4), 92.875 (5), 95.995 (5) |
V (Å3) | 686.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.43 × 0.28 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.538, 0.701 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6579, 2416, 2308 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.069, 1.13 |
No. of reflections | 2416 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.43 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
C13—S | 1.805 (4) | S—C6 | 1.783 (3) |
C12—Pd1 | 1.977 (3) | Cl2—C10 | 1.739 (4) |
Pd1—N1 | 1.972 (3) | N1—N2 | 1.270 (4) |
Pd1—Cl1 | 2.2900 (11) | N1—C1 | 1.433 (4) |
Pd1—S | 2.3810 (10) | N2—C7 | 1.401 (4) |
N1—Pd1—C12 | 79.36 (13) | C6—S—C13 | 102.51 (17) |
C12—Pd1—Cl1 | 96.12 (10) | N2—N1—C1 | 118.2 (3) |
N1—Pd1—S | 85.42 (9) | N1—N2—C7 | 110.3 (3) |
Cl1—Pd1—S | 98.98 (4) | ||
C13—S—C6—C1 | 121.4 (3) | Pd1—S—C6—C1 | 7.3 (3) |
Cyclopalladated compounds have numerous applications (Dupont et al., 2005) in organic synthesis, catalysis, photochemistry and metallomesogen chemistry. Although a number of cyclometallated complexes of palladium (Omae, 2004 & Neogi et al., 2006) have been reported in literature, report of palladium complexes with sulfur as an auxiliary donor is relatively sparse (Pal et al., 1992). Against this background, we report here the crystal structure of (I).
The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The palladium atom along with donor set of four atoms lie in an almost plane. Selected bond lengths and bond angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N?N bond length is typical of other cyclopalladated azoarenes (Neogi et al., 2006), unlike that of other free azoarenes containing thioether moiety (Das et al., 2006). The metal carbon bond length, 1.977 (3) Å, is higher than the reported values of other ortho-palladated azoarenes (Bagchi & Bandyopadhyay, 2007). The molecules are found to dimerize through a nonbonded S···S interaction; having S···Si [symmetry code: (i) 1 - x, -y, 1 - z] distance of 3.5162 (17) Å (Chattopadhyay et al., 1991) (Fig. 3). Four inter molecular π—π interactions (Kubo et al., 2005 & Bagchi & Bandyopadhyay, 2007) arrange the molecules in anti parallel fashion (Fig. 4). The Cg3—Cg4ii, Cg3—Cg4iii, Cg4—Cg3ii, Cg4—Cg3iii, [symmetry codes: (ii) -x, 1 - y, 1 - z; (iii) 1 - x, 1 - y, 1-z. Cg3 and Cg4 are the centroids of C1—C6 and C7—C12 rings, respectively.] distances are 3.808 (2), 3.623 (2), 3.808 (2) and 3.623 (2) Å; the corresponding perpendicular distances are 3.462, 3.454, 3.402 and 3.402 Å with slippages of 3.402, 3.402, 3.462 and 3.454 Å, respectively.