organic compounds
N,N,N-tris[(1,3-benzothiazol-2-yl)methyl]amine
ofaDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
*Correspondence e-mail: dmanke@umassd.edu
The title compound, C24H18N4S3, exhibits three near planar benzothiazole systems in a pseudo-C3 conformation. The dihedral angles between the planes of the benzothiazole groups range from 112.56 (4) to 124.68 (4)° In the crystal, molecules are connected to each other through three short C—H⋯N contacts, forming an infinite chain along [100]. The molecules are also linked by π–π interactions with each of the three five-membered thiazole rings. [inter-centroid distance range: 3.614 (1)–4.074 (1) Å, inter-planar distance range: 3.4806 (17)–3.6902 (15) Å, slippage range: 0.759 (3)–1.887 (3) Å].
Keywords: crystal structure; benzothiazoles; C—H⋯N interactions.
CCDC reference: 1425576
1. Related literature
For synthesis of the title compound and a structure of the ligand bound to copper, see: Thompson et al. (1980). For a related organic structure, see: Zhang et al. (2009). For other related structures, see; Bautista & Thompson (1980); Pandey & Mathur (1995). For a study of its use as a ligand in azide–alkyne cycloadditions, see: Rodionov, Presolski, Gardinier et al. (2007); Rodionov, Presolski, Diaz et al. (2007).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1425576
10.1107/S2056989015017417/ff2141sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017417/ff2141Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017417/ff2141Isup3.txt
Supporting information file. DOI: 10.1107/S2056989015017417/ff2141Isup4.cml
Tripodal ligands with nitrogen donors have become a common motif in coordination chemistry. Herein we report the structure of tris(benzothiazolylmethyl)amine. The bond distances and angles of the complex are similar to the previously reported bis(benzothiazol-2-ylmethyl)amine (Zhang et al., 2009). Copper and cobalt complexes of this ligand have been synthesized (Bautista & Thompson, 1980; Thompson et al., 1980, Pandey & Mathur, 1995) and copper complexes have been explored as catalysts for azide-alkyne cycloadditions (Rodionov, Presolski, Diaz, et al., 2007; Rodionov, Presolski, Gardinier, et al. 2007).
The molecular structure of the title compound is shown in Figure 1. The compound possesses three planar benzothiazoles that demonstrate a pseudo-C3 configuration. The planes of the three benzothiazole ligands exhibit dihedral angles of 112.555 (2), 123.744 (2) and 124.677 (3). The structure exhibits infinite chains along [100] which result from three C—H···N short contacts. The packing of the title compound is shown in Figure 2.
The compound was prepared by literature procedure (Thompson et al., 1980). Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a diethyl ether solution.
The structure was solved by
and all non-hydrogen atoms were refined anisotropically by full matrix least squares on F2. Hydrogen atoms were placed in calculated positions and then refined with riding models with C—H lengths of 0.99 Å for (CH2) and 0.95 Å for (CH) with isotropic displacement parameters set to 1.20 times Ueq of the parent C atoms. Diffused solvent (ethyl ether) was treated using Platon (Spek, 2009) program SQUEEZE (found void 157Å3, 48 electrons) and the unit card was adjusted by C4H10O to address issues of chemical formula, molecular and F000 value.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).C24H18N4S3 | Z = 2 |
Mr = 495.66 | F(000) = 518 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6530 (3) Å | Cell parameters from 6510 reflections |
b = 14.3098 (6) Å | θ = 3.1–25.7° |
c = 14.5822 (7) Å | µ = 0.34 mm−1 |
α = 61.471 (1)° | T = 100 K |
β = 88.474 (2)° | Block, yellow |
γ = 79.138 (1)° | 0.15 × 0.12 × 0.10 mm |
V = 1194.61 (9) Å3 |
Bruker APEXII CCD diffractometer | 4691 independent reflections |
Radiation source: fine-focus ROTATING ANODE | 3767 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.0000 |
φ and ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→8 |
Tmin = 0.951, Tmax = 0.967 | k = −15→17 |
4691 measured reflections | l = 0→17 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.0926P] where P = (Fo2 + 2Fc2)/3 |
4691 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C24H18N4S3 | γ = 79.138 (1)° |
Mr = 495.66 | V = 1194.61 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.6530 (3) Å | Mo Kα radiation |
b = 14.3098 (6) Å | µ = 0.34 mm−1 |
c = 14.5822 (7) Å | T = 100 K |
α = 61.471 (1)° | 0.15 × 0.12 × 0.10 mm |
β = 88.474 (2)° |
Bruker APEXII CCD diffractometer | 4691 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3767 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.967 | Rint = 0.0000 |
4691 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.28 e Å−3 |
4691 reflections | Δρmin = −0.29 e Å−3 |
280 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 | ||
S1 | 0.40279 (7) | 0.15702 (4) | 0.47208 (4) | 0.04313 (15) | |
S2 | 0.27604 (8) | 0.38911 (4) | 0.15881 (4) | 0.04461 (16) | |
S3 | 0.25502 (7) | 0.44886 (4) | 0.38876 (5) | 0.04767 (16) | |
N1 | 0.1195 (2) | 0.05355 (12) | 0.57200 (13) | 0.0416 (4) | |
N2 | −0.0211 (2) | 0.34050 (12) | 0.08966 (12) | 0.0405 (4) | |
N3 | −0.1239 (2) | 0.54789 (12) | 0.36542 (12) | 0.0382 (4) | |
N4 | −0.0043 (2) | 0.30973 (12) | 0.34526 (12) | 0.0368 (4) | |
C1 | 0.0012 (3) | 0.19336 (15) | 0.39103 (15) | 0.0418 (5) | |
H1B | 0.0358 | 0.1702 | 0.3375 | 0.050* | |
H1A | −0.1361 | 0.1784 | 0.4139 | 0.050* | |
C2 | 0.1562 (3) | 0.13010 (14) | 0.48240 (15) | 0.0384 (4) | |
C3 | 0.4652 (3) | 0.05555 (14) | 0.60010 (15) | 0.0387 (4) | |
C4 | 0.6507 (3) | 0.01905 (15) | 0.66060 (18) | 0.0483 (5) | |
H4A | 0.7686 | 0.0480 | 0.6318 | 0.058* | |
C5 | 0.6574 (3) | −0.06029 (16) | 0.76342 (18) | 0.0558 (6) | |
H5A | 0.7813 | −0.0853 | 0.8064 | 0.067* | |
C6 | 0.4877 (4) | −0.10437 (17) | 0.8055 (2) | 0.0628 (6) | |
H6A | 0.4962 | −0.1581 | 0.8770 | 0.075* | |
C7 | 0.3052 (3) | −0.07124 (16) | 0.74462 (18) | 0.0570 (6) | |
H7A | 0.1903 | −0.1035 | 0.7731 | 0.068* | |
C8 | 0.2940 (3) | 0.00976 (13) | 0.64160 (16) | 0.0403 (4) | |
C9 | −0.1080 (3) | 0.37025 (16) | 0.23985 (15) | 0.0424 (5) | |
H9A | −0.1536 | 0.4475 | 0.2214 | 0.051* | |
H9B | −0.2311 | 0.3412 | 0.2388 | 0.051* | |
C10 | 0.0308 (3) | 0.36203 (14) | 0.16109 (14) | 0.0374 (4) | |
C11 | 0.3140 (3) | 0.37193 (14) | 0.04962 (14) | 0.0375 (4) | |
C12 | 0.4860 (3) | 0.37765 (15) | −0.00699 (15) | 0.0440 (5) | |
H12A | 0.6035 | 0.3968 | 0.0099 | 0.053* | |
C13 | 0.4821 (3) | 0.35475 (16) | −0.08855 (15) | 0.0473 (5) | |
H13A | 0.5984 | 0.3582 | −0.1284 | 0.057* | |
C14 | 0.3113 (3) | 0.32676 (17) | −0.11319 (16) | 0.0521 (5) | |
H14A | 0.3129 | 0.3104 | −0.1692 | 0.063* | |
C15 | 0.1381 (3) | 0.32219 (17) | −0.05775 (16) | 0.0501 (5) | |
H15A | 0.0205 | 0.3039 | −0.0758 | 0.060* | |
C16 | 0.1393 (3) | 0.34469 (14) | 0.02442 (14) | 0.0377 (4) | |
C17 | −0.0894 (3) | 0.35415 (15) | 0.41340 (16) | 0.0411 (4) | |
H17A | −0.0500 | 0.2993 | 0.4875 | 0.049* | |
H17B | −0.2410 | 0.3719 | 0.4032 | 0.049* | |
C18 | −0.0096 (3) | 0.45492 (15) | 0.38820 (14) | 0.0375 (4) | |
C19 | 0.2093 (3) | 0.58523 (15) | 0.35501 (14) | 0.0385 (4) | |
C20 | 0.3495 (3) | 0.65143 (16) | 0.33751 (17) | 0.0477 (5) | |
H20A | 0.4930 | 0.6233 | 0.3468 | 0.057* | |
C21 | 0.2730 (4) | 0.75976 (17) | 0.30610 (18) | 0.0531 (5) | |
H21A | 0.3657 | 0.8073 | 0.2922 | 0.064* | |
C22 | 0.0642 (3) | 0.80027 (16) | 0.29458 (17) | 0.0521 (5) | |
H22A | 0.0159 | 0.8752 | 0.2726 | 0.062* | |
C23 | −0.0763 (3) | 0.73355 (16) | 0.31451 (17) | 0.0486 (5) | |
H23A | −0.2196 | 0.7617 | 0.3073 | 0.058* | |
C24 | −0.0023 (3) | 0.62444 (14) | 0.34531 (14) | 0.0364 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0398 (3) | 0.0435 (3) | 0.0487 (3) | −0.0190 (2) | 0.0104 (2) | −0.0209 (2) |
S2 | 0.0367 (3) | 0.0614 (3) | 0.0469 (3) | −0.0167 (2) | 0.0027 (2) | −0.0324 (3) |
S3 | 0.0343 (3) | 0.0435 (3) | 0.0722 (4) | −0.0075 (2) | 0.0131 (2) | −0.0339 (3) |
N1 | 0.0365 (9) | 0.0334 (8) | 0.0527 (10) | −0.0113 (7) | 0.0097 (8) | −0.0179 (8) |
N2 | 0.0331 (8) | 0.0457 (9) | 0.0415 (9) | −0.0078 (7) | −0.0041 (7) | −0.0197 (8) |
N3 | 0.0354 (8) | 0.0461 (9) | 0.0381 (9) | −0.0046 (7) | 0.0009 (7) | −0.0253 (7) |
N4 | 0.0352 (8) | 0.0386 (8) | 0.0390 (9) | −0.0090 (7) | 0.0041 (7) | −0.0201 (7) |
C1 | 0.0392 (11) | 0.0432 (10) | 0.0479 (12) | −0.0160 (8) | 0.0061 (9) | −0.0232 (9) |
C2 | 0.0373 (10) | 0.0346 (9) | 0.0504 (12) | −0.0123 (8) | 0.0103 (9) | −0.0247 (9) |
C3 | 0.0369 (10) | 0.0308 (9) | 0.0528 (12) | −0.0070 (8) | 0.0085 (9) | −0.0237 (9) |
C4 | 0.0384 (11) | 0.0405 (10) | 0.0672 (15) | −0.0057 (9) | 0.0051 (10) | −0.0277 (11) |
C5 | 0.0469 (13) | 0.0415 (11) | 0.0648 (15) | 0.0036 (9) | −0.0063 (11) | −0.0183 (11) |
C6 | 0.0592 (15) | 0.0426 (12) | 0.0606 (15) | 0.0021 (11) | 0.0007 (12) | −0.0085 (11) |
C7 | 0.0500 (13) | 0.0374 (11) | 0.0658 (15) | −0.0093 (9) | 0.0130 (11) | −0.0110 (11) |
C8 | 0.0378 (10) | 0.0288 (9) | 0.0525 (12) | −0.0066 (8) | 0.0088 (9) | −0.0184 (9) |
C9 | 0.0331 (10) | 0.0485 (11) | 0.0446 (11) | −0.0055 (8) | −0.0005 (8) | −0.0225 (9) |
C10 | 0.0324 (10) | 0.0362 (9) | 0.0390 (11) | −0.0056 (8) | −0.0043 (8) | −0.0146 (8) |
C11 | 0.0368 (10) | 0.0353 (9) | 0.0334 (10) | −0.0069 (8) | −0.0041 (8) | −0.0109 (8) |
C12 | 0.0406 (11) | 0.0473 (11) | 0.0415 (11) | −0.0137 (9) | 0.0020 (9) | −0.0176 (9) |
C13 | 0.0490 (12) | 0.0500 (12) | 0.0358 (11) | −0.0078 (9) | 0.0037 (9) | −0.0158 (9) |
C14 | 0.0560 (14) | 0.0618 (13) | 0.0373 (11) | −0.0071 (11) | −0.0024 (10) | −0.0244 (10) |
C15 | 0.0468 (12) | 0.0616 (13) | 0.0448 (12) | −0.0143 (10) | −0.0070 (10) | −0.0263 (10) |
C16 | 0.0376 (10) | 0.0362 (9) | 0.0334 (10) | −0.0043 (8) | −0.0069 (8) | −0.0126 (8) |
C17 | 0.0345 (10) | 0.0463 (11) | 0.0481 (12) | −0.0117 (8) | 0.0106 (9) | −0.0261 (9) |
C18 | 0.0350 (10) | 0.0444 (10) | 0.0371 (10) | −0.0087 (8) | 0.0070 (8) | −0.0228 (9) |
C19 | 0.0393 (11) | 0.0428 (10) | 0.0401 (11) | −0.0071 (8) | 0.0080 (8) | −0.0258 (9) |
C20 | 0.0420 (11) | 0.0521 (12) | 0.0616 (13) | −0.0119 (9) | 0.0134 (10) | −0.0368 (11) |
C21 | 0.0573 (14) | 0.0525 (12) | 0.0647 (15) | −0.0193 (10) | 0.0162 (11) | −0.0379 (11) |
C22 | 0.0600 (14) | 0.0419 (11) | 0.0588 (14) | −0.0065 (10) | 0.0019 (11) | −0.0290 (10) |
C23 | 0.0453 (12) | 0.0484 (11) | 0.0535 (13) | 0.0009 (9) | −0.0042 (10) | −0.0290 (10) |
C24 | 0.0387 (10) | 0.0426 (10) | 0.0330 (10) | −0.0058 (8) | 0.0010 (8) | −0.0230 (8) |
S1—C3 | 1.729 (2) | C7—H7A | 0.9500 |
S1—C2 | 1.7415 (18) | C9—C10 | 1.489 (3) |
S2—C11 | 1.729 (2) | C9—H9A | 0.9900 |
S2—C10 | 1.7423 (18) | C9—H9B | 0.9900 |
S3—C19 | 1.7349 (18) | C11—C12 | 1.385 (3) |
S3—C18 | 1.7460 (18) | C11—C16 | 1.403 (3) |
N1—C2 | 1.297 (2) | C12—C13 | 1.378 (3) |
N1—C8 | 1.397 (2) | C12—H12A | 0.9500 |
N2—C10 | 1.290 (2) | C13—C14 | 1.383 (3) |
N2—C16 | 1.401 (2) | C13—H13A | 0.9500 |
N3—C18 | 1.292 (2) | C14—C15 | 1.384 (3) |
N3—C24 | 1.398 (2) | C14—H14A | 0.9500 |
N4—C1 | 1.462 (2) | C15—C16 | 1.382 (3) |
N4—C9 | 1.466 (2) | C15—H15A | 0.9500 |
N4—C17 | 1.466 (2) | C17—C18 | 1.506 (2) |
C1—C2 | 1.493 (3) | C17—H17A | 0.9900 |
C1—H1B | 0.9900 | C17—H17B | 0.9900 |
C1—H1A | 0.9900 | C19—C20 | 1.386 (3) |
C3—C4 | 1.396 (3) | C19—C24 | 1.398 (3) |
C3—C8 | 1.399 (3) | C20—C21 | 1.381 (3) |
C4—C5 | 1.377 (3) | C20—H20A | 0.9500 |
C4—H4A | 0.9500 | C21—C22 | 1.382 (3) |
C5—C6 | 1.382 (3) | C21—H21A | 0.9500 |
C5—H5A | 0.9500 | C22—C23 | 1.388 (3) |
C6—C7 | 1.388 (3) | C22—H22A | 0.9500 |
C6—H6A | 0.9500 | C23—C24 | 1.391 (3) |
C7—C8 | 1.384 (3) | C23—H23A | 0.9500 |
C3—S1—C2 | 89.03 (9) | C12—C11—C16 | 121.21 (18) |
C11—S2—C10 | 89.09 (9) | C12—C11—S2 | 129.24 (15) |
C19—S3—C18 | 89.02 (9) | C16—C11—S2 | 109.49 (14) |
C2—N1—C8 | 110.35 (15) | C13—C12—C11 | 118.16 (19) |
C10—N2—C16 | 110.28 (15) | C13—C12—H12A | 120.9 |
C18—N3—C24 | 110.23 (15) | C11—C12—H12A | 120.9 |
C1—N4—C9 | 111.51 (14) | C12—C13—C14 | 120.96 (19) |
C1—N4—C17 | 112.81 (14) | C12—C13—H13A | 119.5 |
C9—N4—C17 | 112.20 (14) | C14—C13—H13A | 119.5 |
N4—C1—C2 | 110.82 (14) | C13—C14—C15 | 121.1 (2) |
N4—C1—H1B | 109.5 | C13—C14—H14A | 119.4 |
C2—C1—H1B | 109.5 | C15—C14—H14A | 119.4 |
N4—C1—H1A | 109.5 | C16—C15—C14 | 118.71 (19) |
C2—C1—H1A | 109.5 | C16—C15—H15A | 120.6 |
H1B—C1—H1A | 108.1 | C14—C15—H15A | 120.6 |
N1—C2—C1 | 123.72 (17) | C15—C16—N2 | 125.52 (18) |
N1—C2—S1 | 116.22 (15) | C15—C16—C11 | 119.80 (18) |
C1—C2—S1 | 120.06 (13) | N2—C16—C11 | 114.66 (16) |
C4—C3—C8 | 120.91 (18) | N4—C17—C18 | 109.94 (14) |
C4—C3—S1 | 129.40 (15) | N4—C17—H17A | 109.7 |
C8—C3—S1 | 109.69 (14) | C18—C17—H17A | 109.7 |
C5—C4—C3 | 117.91 (19) | N4—C17—H17B | 109.7 |
C5—C4—H4A | 121.0 | C18—C17—H17B | 109.7 |
C3—C4—H4A | 121.0 | H17A—C17—H17B | 108.2 |
C4—C5—C6 | 121.4 (2) | N3—C18—C17 | 124.56 (16) |
C4—C5—H5A | 119.3 | N3—C18—S3 | 116.31 (14) |
C6—C5—H5A | 119.3 | C17—C18—S3 | 119.13 (14) |
C5—C6—C7 | 120.9 (2) | C20—C19—C24 | 121.92 (17) |
C5—C6—H6A | 119.6 | C20—C19—S3 | 128.84 (15) |
C7—C6—H6A | 119.6 | C24—C19—S3 | 109.24 (13) |
C8—C7—C6 | 118.6 (2) | C21—C20—C19 | 117.64 (19) |
C8—C7—H7A | 120.7 | C21—C20—H20A | 121.2 |
C6—C7—H7A | 120.7 | C19—C20—H20A | 121.2 |
C7—C8—N1 | 125.12 (18) | C20—C21—C22 | 121.2 (2) |
C7—C8—C3 | 120.18 (19) | C20—C21—H21A | 119.4 |
N1—C8—C3 | 114.70 (17) | C22—C21—H21A | 119.4 |
N4—C9—C10 | 111.13 (15) | C21—C22—C23 | 121.23 (19) |
N4—C9—H9A | 109.4 | C21—C22—H22A | 119.4 |
C10—C9—H9A | 109.4 | C23—C22—H22A | 119.4 |
N4—C9—H9B | 109.4 | C22—C23—C24 | 118.42 (19) |
C10—C9—H9B | 109.4 | C22—C23—H23A | 120.8 |
H9A—C9—H9B | 108.0 | C24—C23—H23A | 120.8 |
N2—C10—C9 | 124.19 (17) | C23—C24—N3 | 125.21 (17) |
N2—C10—S2 | 116.46 (15) | C23—C24—C19 | 119.57 (17) |
C9—C10—S2 | 119.28 (14) | N3—C24—C19 | 115.20 (16) |
C9—N4—C1—C2 | 163.44 (15) | C11—C12—C13—C14 | 0.0 (3) |
C17—N4—C1—C2 | −69.23 (19) | C12—C13—C14—C15 | 0.8 (3) |
C8—N1—C2—C1 | −179.97 (16) | C13—C14—C15—C16 | −0.9 (3) |
C8—N1—C2—S1 | 0.3 (2) | C14—C15—C16—N2 | −178.09 (17) |
N4—C1—C2—N1 | 132.22 (18) | C14—C15—C16—C11 | 0.3 (3) |
N4—C1—C2—S1 | −48.1 (2) | C10—N2—C16—C15 | 177.63 (18) |
C3—S1—C2—N1 | 0.28 (15) | C10—N2—C16—C11 | −0.8 (2) |
C3—S1—C2—C1 | −179.47 (15) | C12—C11—C16—C15 | 0.5 (3) |
C2—S1—C3—C4 | 179.89 (18) | S2—C11—C16—C15 | −177.11 (15) |
C2—S1—C3—C8 | −0.75 (14) | C12—C11—C16—N2 | 179.05 (16) |
C8—C3—C4—C5 | −2.5 (3) | S2—C11—C16—N2 | 1.42 (19) |
S1—C3—C4—C5 | 176.78 (16) | C1—N4—C17—C18 | 155.22 (15) |
C3—C4—C5—C6 | 1.2 (3) | C9—N4—C17—C18 | −77.82 (19) |
C4—C5—C6—C7 | 1.1 (4) | C24—N3—C18—C17 | −179.50 (16) |
C5—C6—C7—C8 | −2.2 (3) | C24—N3—C18—S3 | 0.4 (2) |
C6—C7—C8—N1 | −178.05 (19) | N4—C17—C18—N3 | 126.01 (19) |
C6—C7—C8—C3 | 0.9 (3) | N4—C17—C18—S3 | −53.8 (2) |
C2—N1—C8—C7 | 178.12 (19) | C19—S3—C18—N3 | 0.05 (15) |
C2—N1—C8—C3 | −0.9 (2) | C19—S3—C18—C17 | 179.91 (15) |
C4—C3—C8—C7 | 1.4 (3) | C18—S3—C19—C20 | −179.60 (19) |
S1—C3—C8—C7 | −177.98 (16) | C18—S3—C19—C24 | −0.43 (14) |
C4—C3—C8—N1 | −179.48 (16) | C24—C19—C20—C21 | −2.3 (3) |
S1—C3—C8—N1 | 1.1 (2) | S3—C19—C20—C21 | 176.77 (16) |
C1—N4—C9—C10 | −79.28 (18) | C19—C20—C21—C22 | 1.3 (3) |
C17—N4—C9—C10 | 153.06 (15) | C20—C21—C22—C23 | 0.2 (3) |
C16—N2—C10—C9 | 176.60 (16) | C21—C22—C23—C24 | −0.8 (3) |
C16—N2—C10—S2 | −0.2 (2) | C22—C23—C24—N3 | −178.19 (18) |
N4—C9—C10—N2 | 133.35 (18) | C22—C23—C24—C19 | −0.2 (3) |
N4—C9—C10—S2 | −49.92 (19) | C18—N3—C24—C23 | 177.37 (18) |
C11—S2—C10—N2 | 0.87 (15) | C18—N3—C24—C19 | −0.7 (2) |
C11—S2—C10—C9 | −176.10 (15) | C20—C19—C24—C23 | 1.8 (3) |
C10—S2—C11—C12 | −178.60 (18) | S3—C19—C24—C23 | −177.46 (14) |
C10—S2—C11—C16 | −1.23 (13) | C20—C19—C24—N3 | 179.98 (17) |
C16—C11—C12—C13 | −0.6 (3) | S3—C19—C24—N3 | 0.7 (2) |
S2—C11—C12—C13 | 176.48 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···N1i | 0.95 | 2.47 | 3.376 (3) | 159 |
C12—H12A···N2i | 0.95 | 2.60 | 3.449 (2) | 150 |
C20—H20A···N3i | 0.95 | 2.54 | 3.490 (3) | 178 |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···N1i | 0.9500 | 2.4700 | 3.376 (3) | 158.9 |
C12—H12A···N2i | 0.9500 | 2.6000 | 3.449 (2) | 149.5 |
C20—H20A···N3i | 0.9500 | 2.5400 | 3.490 (3) | 177.9 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
We gratefully acknowledge support from the National Science Foundation (CHE-1229339 and CHE-1429086).
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