organic compounds
1-Methyl-3-phenylimidazolidine-2-thione
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com
The 10H12N2S, comprises two molecules, each of which has a twist about the CH2—CH2 bond within the five-membered ring. The major difference between the independent molecules is manifested in the relative orientations of the five- and six-membered rings [dihedral angles between the least-squares planes = 28.03 (11) and 41.54 (11)°]. A network of C—H⋯π interactions consolidates the three-dimensional crystal packing.
of the title cyclic thiourea derivative, CCCDC reference: 987460
Related literature
For the biological activity of phosphinegold(I) species of related molecules, see: Henderson et al. (2006). For the structure of dimethyl-2-imidazolidinethione, see: Chieh & Cheung (1983).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Gans & Shalloway (2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 987460
10.1107/S1600536814003626/hg5384sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003626/hg5384Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003626/hg5384Isup3.cml
In connection with studies of the biological activities of phosphine gold(I) species of functionalized thiourea derivatives (Henderson et al., 2006), the title compound, (I), was synthesised. The crystallographic
contains two independent molecules, Fig. 1. Each molecule is twisted about the CH2—CH2 bond. From the overlay diagram of the S1-containing molecule with the inverted S2-containing molecule, Fig. 2, only a small difference in the relative orientations of the phenyl groups is noted, as quantified in the C2—N2—C5—C10 and C12—N4—C15—C20 torsion angles of 35.6 (3) and -42.8 (3)°, respectively. The twisted conformation in (I) contrasts the near planar structure of the dimethyl-2-imidazolidinethione derivative (Chieh & Cheung, 1983).The three-dimensional crystal packing is sustained by C—H···π interactions, Table 1, involving phenyl- and methyl-H interacting with each of the phenyl rings, with each ring accepting two interactions, Fig. 3.
The title compound, (I), was prepared in two steps. 2-Methylamino ethanol (10 mmol, 0.82 ml) was dissolved in absolute ethanol (5 ml). Phenyl isothiocyanate (10.1 mmol, 1.24 ml) was added drop wise to the solution over 30 mins. The solution changed from colourless to light-yellow and left to stir for 3 h. Distilled water was added to the mixture resulting in a white precipitate. The precipitate was filtered off and washed with distilled water and a small amount of diethyl ether. Yield: 90% (1.8923 g, 8.9981 mmol) of white powder. The crystals are obtained from slow evaporation of this powder in absolute ethanol. M.pt: 375.8–376.0 K. This powder was subsequently used in the next reaction.
1-(2-Hydroxyethyl)-1-methyl-3-phenylthiourea (9.03 mmol, 1.8963 g) was dissolved in dry THF (7 ml). Sodium hydride (9 mmol, 0.36 g) in dry THF (6 ml) was added drop wise at room temperature, under nitrogen and with stirring for 1 h. The solvent was removed and the white powder was washed with diethyl ether, and taken up in DMSO (4 ml). Phenyl isothiocyanate (4 mmol, 0.48 ml) was added drop wise to the solution. The mixture was heated at 323 K and stirred for 5 h. A clear yellow solution was observed which was cooled to room temperature. Cold distilled water was added with further stirring for 30 min. whereupon a yellow precipitate formed. The precipitate was filtered off and washed with water and hexane. Yield: 71% (0.5469 g, 2.8443 mmol) of a white powder. Crystals were obtained by slow evaporation from its absolute ethanol solution; M.pt: 404.7–404.9 K. IR (νmax, cm-1): 2977 and 2899 (CH2), 1085 (C=S), 1613, 1598 and 1565 (aromatic C=C). 1H NMR (CDCl3): δ 3.42 (d, CH3, 6.76 Hz), 3.64 (t, CH2, 4.12 Hz), 3.92 (t, CH2, 4.32 Hz), 7.13 (t, aromatic-H, 7.24 Hz), 7.31 (t, aromatic-H, 7.38 Hz), 7.39 (d, aromatic-H, 7.80 Hz) ppm.
The C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). Owing to poor agreement, two reflections, i.e. (2 0 1) and (4 0 1), were omitted from the final cycles of
The studied crystal is a racemic twin with the minor component being 0.117 (14).Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Gans & Shalloway (2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the two independent molecules comprising the asymmetric unit in (I), showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. Overlay diagram of the S1-containing (red image) and inverted S2-containing (blue) molecules drawn so that the heteroatoms overlap. | |
Fig. 3. A view of the unit-cell contents of (I) in projection down the a axis. The C—H···π interactions are shown as purple dashed lines. |
C10H12N2S | F(000) = 816 |
Mr = 192.28 | Dx = 1.329 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3909 reflections |
a = 7.5159 (1) Å | θ = 4.0–76.3° |
b = 14.0478 (3) Å | µ = 2.59 mm−1 |
c = 18.2050 (3) Å | T = 100 K |
V = 1922.12 (6) Å3 | Prism, colourless |
Z = 8 | 0.20 × 0.10 × 0.05 mm |
Agilent SuperNova Dual diffractometer with an Atlas detector | 3955 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3814 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.026 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 76.5°, θmin = 4.0° |
ω scan | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −16→17 |
Tmin = 0.427, Tmax = 1.000 | l = −22→22 |
7245 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.4944P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3955 reflections | Δρmax = 0.39 e Å−3 |
238 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1665 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.117 (14) |
C10H12N2S | V = 1922.12 (6) Å3 |
Mr = 192.28 | Z = 8 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.5159 (1) Å | µ = 2.59 mm−1 |
b = 14.0478 (3) Å | T = 100 K |
c = 18.2050 (3) Å | 0.20 × 0.10 × 0.05 mm |
Agilent SuperNova Dual diffractometer with an Atlas detector | 3955 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 3814 reflections with I > 2σ(I) |
Tmin = 0.427, Tmax = 1.000 | Rint = 0.026 |
7245 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.090 | Δρmax = 0.39 e Å−3 |
S = 1.08 | Δρmin = −0.26 e Å−3 |
3955 reflections | Absolute structure: Flack (1983), 1665 Friedel pairs |
238 parameters | Absolute structure parameter: 0.117 (14) |
0 restraints |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
S1 | 0.95401 (6) | 0.92442 (3) | 0.80811 (2) | 0.02271 (12) | |
N1 | 0.9949 (2) | 1.11210 (11) | 0.82471 (8) | 0.0216 (3) | |
N2 | 0.9877 (2) | 1.07023 (11) | 0.70835 (8) | 0.0185 (3) | |
C1 | 0.9816 (3) | 1.10938 (15) | 0.90394 (10) | 0.0291 (4) | |
H1A | 0.9392 | 1.0465 | 0.9194 | 0.044* | |
H1B | 0.8978 | 1.1583 | 0.9205 | 0.044* | |
H1C | 1.0989 | 1.1215 | 0.9255 | 0.044* | |
C2 | 0.9780 (3) | 1.03784 (13) | 0.77947 (10) | 0.0188 (4) | |
C3 | 1.0070 (3) | 1.20270 (13) | 0.78616 (10) | 0.0229 (4) | |
H3A | 1.1056 | 1.2422 | 0.8055 | 0.027* | |
H3B | 0.8943 | 1.2389 | 0.7896 | 0.027* | |
C4 | 1.0434 (3) | 1.17071 (13) | 0.70745 (10) | 0.0212 (4) | |
H4A | 0.9724 | 1.2081 | 0.6719 | 0.025* | |
H4B | 1.1711 | 1.1768 | 0.6951 | 0.025* | |
C5 | 0.9852 (2) | 1.01694 (13) | 0.64236 (9) | 0.0185 (4) | |
C6 | 1.0800 (3) | 1.05145 (13) | 0.58225 (10) | 0.0228 (4) | |
H6 | 1.1489 | 1.1078 | 0.5869 | 0.027* | |
C7 | 1.0738 (3) | 1.00333 (15) | 0.51530 (11) | 0.0275 (4) | |
H7 | 1.1380 | 1.0275 | 0.4744 | 0.033* | |
C8 | 0.9753 (3) | 0.92088 (14) | 0.50772 (10) | 0.0278 (4) | |
H8 | 0.9729 | 0.8878 | 0.4622 | 0.033* | |
C9 | 0.8798 (3) | 0.88714 (14) | 0.56760 (11) | 0.0253 (4) | |
H9 | 0.8117 | 0.8305 | 0.5626 | 0.030* | |
C10 | 0.8816 (3) | 0.93438 (13) | 0.63471 (10) | 0.0211 (4) | |
H10 | 0.8137 | 0.9111 | 0.6749 | 0.025* | |
S2 | 1.01213 (7) | 0.84486 (3) | 0.30525 (2) | 0.02324 (12) | |
N4 | 0.9717 (2) | 0.70117 (11) | 0.20545 (8) | 0.0194 (3) | |
N3 | 0.9499 (2) | 0.65787 (11) | 0.32123 (8) | 0.0217 (3) | |
C11 | 0.9083 (3) | 0.66426 (14) | 0.39877 (10) | 0.0261 (4) | |
H11A | 0.9590 | 0.7230 | 0.4190 | 0.039* | |
H11B | 0.9588 | 0.6093 | 0.4245 | 0.039* | |
H11C | 0.7789 | 0.6649 | 0.4053 | 0.039* | |
C12 | 0.9758 (3) | 0.73296 (13) | 0.27636 (9) | 0.0184 (4) | |
C13 | 0.9028 (3) | 0.57188 (14) | 0.28070 (10) | 0.0250 (4) | |
H13A | 0.7737 | 0.5585 | 0.2843 | 0.030* | |
H13B | 0.9700 | 0.5161 | 0.2989 | 0.030* | |
C14 | 0.9557 (3) | 0.59672 (12) | 0.20238 (10) | 0.0216 (4) | |
H14A | 1.0703 | 0.5667 | 0.1888 | 0.026* | |
H14B | 0.8631 | 0.5768 | 0.1669 | 0.026* | |
C15 | 0.9922 (3) | 0.75522 (13) | 0.13998 (9) | 0.0180 (4) | |
C16 | 1.0888 (3) | 0.71622 (13) | 0.08195 (10) | 0.0212 (4) | |
H16 | 1.1459 | 0.6564 | 0.0877 | 0.025* | |
C17 | 1.1016 (3) | 0.76506 (14) | 0.01552 (10) | 0.0231 (4) | |
H17 | 1.1672 | 0.7381 | −0.0239 | 0.028* | |
C18 | 1.0197 (3) | 0.85249 (13) | 0.00654 (9) | 0.0209 (4) | |
H18 | 1.0286 | 0.8854 | −0.0389 | 0.025* | |
C19 | 0.9240 (3) | 0.89183 (13) | 0.06463 (10) | 0.0206 (4) | |
H19 | 0.8682 | 0.9520 | 0.0588 | 0.025* | |
C20 | 0.9095 (2) | 0.84342 (13) | 0.13122 (10) | 0.0189 (3) | |
H20 | 0.8436 | 0.8704 | 0.1705 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0319 (2) | 0.0178 (2) | 0.0185 (2) | −0.00049 (17) | 0.00129 (18) | 0.00386 (16) |
N1 | 0.0280 (8) | 0.0183 (7) | 0.0184 (7) | 0.0008 (7) | 0.0005 (6) | −0.0005 (6) |
N2 | 0.0212 (7) | 0.0165 (7) | 0.0177 (7) | 0.0001 (6) | −0.0003 (6) | 0.0007 (6) |
C1 | 0.0415 (12) | 0.0270 (10) | 0.0188 (9) | 0.0019 (9) | 0.0025 (9) | −0.0023 (7) |
C2 | 0.0175 (9) | 0.0191 (9) | 0.0197 (8) | 0.0014 (7) | 0.0017 (7) | 0.0011 (6) |
C3 | 0.0269 (9) | 0.0189 (9) | 0.0229 (8) | 0.0002 (7) | −0.0001 (8) | −0.0004 (7) |
C4 | 0.0261 (9) | 0.0172 (8) | 0.0204 (8) | −0.0032 (7) | −0.0013 (7) | 0.0016 (7) |
C5 | 0.0210 (9) | 0.0191 (8) | 0.0156 (8) | 0.0053 (7) | −0.0016 (7) | 0.0017 (6) |
C6 | 0.0259 (10) | 0.0220 (9) | 0.0205 (9) | 0.0009 (8) | 0.0006 (8) | 0.0021 (7) |
C7 | 0.0341 (11) | 0.0316 (10) | 0.0167 (8) | 0.0056 (9) | 0.0023 (8) | 0.0034 (7) |
C8 | 0.0380 (11) | 0.0275 (10) | 0.0180 (8) | 0.0081 (9) | −0.0046 (8) | −0.0043 (7) |
C9 | 0.0297 (10) | 0.0208 (9) | 0.0253 (9) | 0.0023 (8) | −0.0070 (8) | −0.0011 (8) |
C10 | 0.0232 (9) | 0.0193 (9) | 0.0208 (9) | 0.0008 (7) | −0.0030 (7) | 0.0034 (7) |
S2 | 0.0349 (3) | 0.0177 (2) | 0.0172 (2) | −0.00294 (18) | 0.00142 (19) | −0.00212 (15) |
N4 | 0.0246 (8) | 0.0157 (7) | 0.0180 (7) | −0.0010 (6) | −0.0006 (7) | −0.0006 (6) |
N3 | 0.0273 (8) | 0.0191 (7) | 0.0187 (7) | −0.0009 (6) | 0.0012 (6) | 0.0009 (6) |
C11 | 0.0337 (10) | 0.0246 (9) | 0.0199 (9) | 0.0006 (9) | 0.0021 (8) | 0.0033 (7) |
C12 | 0.0159 (8) | 0.0199 (8) | 0.0193 (8) | 0.0001 (7) | −0.0005 (7) | 0.0007 (6) |
C13 | 0.0317 (10) | 0.0198 (9) | 0.0237 (9) | −0.0036 (8) | −0.0036 (8) | 0.0034 (7) |
C14 | 0.0262 (9) | 0.0149 (8) | 0.0238 (9) | −0.0007 (7) | 0.0014 (8) | −0.0012 (7) |
C15 | 0.0189 (8) | 0.0177 (8) | 0.0174 (8) | −0.0008 (7) | −0.0014 (7) | −0.0015 (6) |
C16 | 0.0233 (9) | 0.0202 (9) | 0.0199 (9) | 0.0026 (7) | −0.0026 (7) | −0.0029 (7) |
C17 | 0.0239 (9) | 0.0282 (10) | 0.0173 (8) | 0.0013 (8) | 0.0015 (8) | −0.0048 (7) |
C18 | 0.0234 (9) | 0.0238 (9) | 0.0156 (8) | −0.0025 (8) | −0.0006 (7) | 0.0011 (7) |
C19 | 0.0227 (9) | 0.0189 (8) | 0.0201 (8) | 0.0013 (7) | −0.0025 (7) | −0.0006 (7) |
C20 | 0.0193 (8) | 0.0194 (8) | 0.0181 (8) | −0.0005 (7) | 0.0009 (7) | −0.0022 (7) |
S1—C2 | 1.6861 (18) | S2—C12 | 1.6800 (19) |
N1—C2 | 1.335 (2) | N4—C12 | 1.366 (2) |
N1—C1 | 1.446 (2) | N4—C15 | 1.422 (2) |
N1—C3 | 1.456 (2) | N4—C14 | 1.473 (2) |
N2—C2 | 1.374 (2) | N3—C12 | 1.348 (2) |
N2—C5 | 1.416 (2) | N3—C11 | 1.449 (2) |
N2—C4 | 1.472 (2) | N3—C13 | 1.459 (2) |
C1—H1A | 0.9800 | C11—H11A | 0.9800 |
C1—H1B | 0.9800 | C11—H11B | 0.9800 |
C1—H1C | 0.9800 | C11—H11C | 0.9800 |
C3—C4 | 1.526 (2) | C13—C14 | 1.521 (3) |
C3—H3A | 0.9900 | C13—H13A | 0.9900 |
C3—H3B | 0.9900 | C13—H13B | 0.9900 |
C4—H4A | 0.9900 | C14—H14A | 0.9900 |
C4—H4B | 0.9900 | C14—H14B | 0.9900 |
C5—C6 | 1.393 (3) | C15—C16 | 1.394 (3) |
C5—C10 | 1.404 (3) | C15—C20 | 1.395 (3) |
C6—C7 | 1.395 (3) | C16—C17 | 1.394 (3) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C7—C8 | 1.381 (3) | C17—C18 | 1.384 (3) |
C7—H7 | 0.9500 | C17—H17 | 0.9500 |
C8—C9 | 1.389 (3) | C18—C19 | 1.393 (3) |
C8—H8 | 0.9500 | C18—H18 | 0.9500 |
C9—C10 | 1.390 (3) | C19—C20 | 1.394 (2) |
C9—H9 | 0.9500 | C19—H19 | 0.9500 |
C10—H10 | 0.9500 | C20—H20 | 0.9500 |
C2—N1—C1 | 126.02 (17) | C12—N4—C15 | 127.96 (16) |
C2—N1—C3 | 113.05 (15) | C12—N4—C14 | 111.30 (15) |
C1—N1—C3 | 120.53 (16) | C15—N4—C14 | 120.60 (15) |
C2—N2—C5 | 128.59 (15) | C12—N3—C11 | 124.96 (16) |
C2—N2—C4 | 110.05 (15) | C12—N3—C13 | 112.11 (15) |
C5—N2—C4 | 120.09 (15) | C11—N3—C13 | 119.44 (16) |
N1—C1—H1A | 109.5 | N3—C11—H11A | 109.5 |
N1—C1—H1B | 109.5 | N3—C11—H11B | 109.5 |
H1A—C1—H1B | 109.5 | H11A—C11—H11B | 109.5 |
N1—C1—H1C | 109.5 | N3—C11—H11C | 109.5 |
H1A—C1—H1C | 109.5 | H11A—C11—H11C | 109.5 |
H1B—C1—H1C | 109.5 | H11B—C11—H11C | 109.5 |
N1—C2—N2 | 108.51 (16) | N3—C12—N4 | 108.27 (16) |
N1—C2—S1 | 123.89 (14) | N3—C12—S2 | 124.46 (14) |
N2—C2—S1 | 127.58 (14) | N4—C12—S2 | 127.25 (14) |
N1—C3—C4 | 101.90 (14) | N3—C13—C14 | 102.74 (15) |
N1—C3—H3A | 111.4 | N3—C13—H13A | 111.2 |
C4—C3—H3A | 111.4 | C14—C13—H13A | 111.2 |
N1—C3—H3B | 111.4 | N3—C13—H13B | 111.2 |
C4—C3—H3B | 111.4 | C14—C13—H13B | 111.2 |
H3A—C3—H3B | 109.3 | H13A—C13—H13B | 109.1 |
N2—C4—C3 | 102.76 (15) | N4—C14—C13 | 102.37 (15) |
N2—C4—H4A | 111.2 | N4—C14—H14A | 111.3 |
C3—C4—H4A | 111.2 | C13—C14—H14A | 111.3 |
N2—C4—H4B | 111.2 | N4—C14—H14B | 111.3 |
C3—C4—H4B | 111.2 | C13—C14—H14B | 111.3 |
H4A—C4—H4B | 109.1 | H14A—C14—H14B | 109.2 |
C6—C5—C10 | 119.56 (17) | C16—C15—C20 | 119.62 (17) |
C6—C5—N2 | 118.41 (17) | C16—C15—N4 | 118.81 (16) |
C10—C5—N2 | 121.91 (16) | C20—C15—N4 | 121.47 (16) |
C5—C6—C7 | 120.06 (19) | C17—C16—C15 | 120.01 (17) |
C5—C6—H6 | 120.0 | C17—C16—H16 | 120.0 |
C7—C6—H6 | 120.0 | C15—C16—H16 | 120.0 |
C8—C7—C6 | 120.76 (19) | C18—C17—C16 | 120.58 (18) |
C8—C7—H7 | 119.6 | C18—C17—H17 | 119.7 |
C6—C7—H7 | 119.6 | C16—C17—H17 | 119.7 |
C7—C8—C9 | 119.00 (18) | C17—C18—C19 | 119.48 (17) |
C7—C8—H8 | 120.5 | C17—C18—H18 | 120.3 |
C9—C8—H8 | 120.5 | C19—C18—H18 | 120.3 |
C8—C9—C10 | 121.45 (19) | C18—C19—C20 | 120.44 (17) |
C8—C9—H9 | 119.3 | C18—C19—H19 | 119.8 |
C10—C9—H9 | 119.3 | C20—C19—H19 | 119.8 |
C9—C10—C5 | 119.15 (18) | C19—C20—C15 | 119.87 (17) |
C9—C10—H10 | 120.4 | C19—C20—H20 | 120.1 |
C5—C10—H10 | 120.4 | C15—C20—H20 | 120.1 |
C1—N1—C2—N2 | 176.14 (19) | C11—N3—C12—N4 | −166.37 (18) |
C3—N1—C2—N2 | 3.5 (2) | C13—N3—C12—N4 | −7.7 (2) |
C1—N1—C2—S1 | −5.2 (3) | C11—N3—C12—S2 | 15.2 (3) |
C3—N1—C2—S1 | −177.86 (15) | C13—N3—C12—S2 | 173.80 (15) |
C5—N2—C2—N1 | 176.60 (18) | C15—N4—C12—N3 | 179.76 (18) |
C4—N2—C2—N1 | 9.7 (2) | C14—N4—C12—N3 | −4.7 (2) |
C5—N2—C2—S1 | −2.0 (3) | C15—N4—C12—S2 | −1.8 (3) |
C4—N2—C2—S1 | −168.90 (15) | C14—N4—C12—S2 | 173.74 (15) |
C2—N1—C3—C4 | −14.2 (2) | C12—N3—C13—C14 | 16.1 (2) |
C1—N1—C3—C4 | 172.68 (19) | C11—N3—C13—C14 | 176.06 (17) |
C2—N2—C4—C3 | −17.8 (2) | C12—N4—C14—C13 | 14.1 (2) |
C5—N2—C4—C3 | 173.97 (16) | C15—N4—C14—C13 | −169.94 (17) |
N1—C3—C4—N2 | 18.21 (19) | N3—C13—C14—N4 | −17.1 (2) |
C2—N2—C5—C6 | −148.43 (19) | C12—N4—C15—C16 | 140.89 (19) |
C4—N2—C5—C6 | 17.4 (3) | C14—N4—C15—C16 | −34.3 (3) |
C2—N2—C5—C10 | 35.6 (3) | C12—N4—C15—C20 | −42.8 (3) |
C4—N2—C5—C10 | −158.57 (17) | C14—N4—C15—C20 | 141.95 (18) |
C10—C5—C6—C7 | −0.9 (3) | C20—C15—C16—C17 | −0.4 (3) |
N2—C5—C6—C7 | −176.94 (18) | N4—C15—C16—C17 | 175.99 (18) |
C5—C6—C7—C8 | −0.5 (3) | C15—C16—C17—C18 | 0.3 (3) |
C6—C7—C8—C9 | 1.0 (3) | C16—C17—C18—C19 | 0.1 (3) |
C7—C8—C9—C10 | −0.1 (3) | C17—C18—C19—C20 | −0.4 (3) |
C8—C9—C10—C5 | −1.3 (3) | C18—C19—C20—C15 | 0.3 (3) |
C6—C5—C10—C9 | 1.8 (3) | C16—C15—C20—C19 | 0.0 (3) |
N2—C5—C10—C9 | 177.65 (17) | N4—C15—C20—C19 | −176.19 (17) |
Cg1 and Cg2 are the centroids of the C5–C10 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11C···Cg1i | 0.98 | 2.96 | 3.759 (2) | 140 |
C19—H19···Cg1ii | 0.95 | 2.85 | 3.612 (2) | 138 |
C6—H6···Cg2iii | 0.95 | 2.89 | 3.719 (2) | 147 |
C17—H17···Cg2iv | 0.95 | 2.76 | 3.577 (2) | 144 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+3/2, −y+2, z−1/2; (iii) −x+5/2, −y+2, z+1/2; (iv) x+1/2, −y+3/2, −z. |
Cg1 and Cg2 are the centroids of the C5–C10 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11C···Cg1i | 0.98 | 2.96 | 3.759 (2) | 140 |
C19—H19···Cg1ii | 0.95 | 2.85 | 3.612 (2) | 138 |
C6—H6···Cg2iii | 0.95 | 2.89 | 3.719 (2) | 147 |
C17—H17···Cg2iv | 0.95 | 2.76 | 3.577 (2) | 144 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+3/2, −y+2, z−1/2; (iii) −x+5/2, −y+2, z+1/2; (iv) x+1/2, −y+3/2, −z. |
Footnotes
‡Additional correspondence author, e-mail: zana@um.edu.my.
Acknowledgements
We gratefully thank the Ministry of Higher Education (Malaysia) and the University of Malaya for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).
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