organic compounds
N-[6-(Dimethylamino)-9-phenyl-3H-telluroxanthen-3-ylidene]-N-methylmethanaminium hexafluorophosphate monoclinic polymorph1
a730 Natural Sciences Complex, University at Buffalo, SUNY, Buffalo, NY 14260-3000, USA, and b771 Natural Sciences Complex, University at Buffalo, SUNY, Buffalo, NY 14260-3000, USA
*Correspondence e-mail: jbb6@buffalo.edu
The title compound C23H23N2Te+·PF6−, is a monoclinic polymorph of the previously reported triclinic structure [Calitree et al. (2007). Organometallics, 26, 6248–6257]. In the crystal, parallel offset π–π stacking [shortest centroid–centroid separation = 3.9620 (9) Å] and ionic interactions help to establish the packing.
Keywords: xanthene; dye; rhodamine; telluroxanthene; crystal structure; polymorph.
CCDC reference: 2085596
Structure description
Chalcogen dyes with near-infrared absorption are used in the targeting of mitochondria of tumors (Detty et al., 1990; Leonard et al., 1999) and enhancing the sensitivity of medical imaging (Bedics et al., 2015; Kryman et al., 2016). The title compound crystallizes with a single C23H23N2Te+ telluroxanthene cation and its PF6− counter-ion in the (Fig. 1). The present monoclinic structure is a polymorph of the previously reported triclinic phase (Calitree et al., 2007; Cambridge Structural Database refcode CIRPAV), which was recrystallized from the mixed solvents of acetonitrile and ether.
The mean plane of the pendant phenyl ring (C19–C23) is nearly orthogonal to the plane of the central telluroxanthene ring (C1/C6/C7/C8/C13/Te1), which subtends a dihedral angle of 70.40 (6)°. The amine bonds (C3—N2 and C11—N1) on either side of the nearly planar telluroxanthene core (r.m.s. deviation = 0.035 Å) are almost the same length [1.343 (3) and 1.347 (3) Å, respectively] indicating delocalization of the positive charge of the cation. The crystal packing is shown in Fig. 2. The telluroxanthene cations form centrosymmetric dimer pairs, which π-stack to form columns propagating parallel to [100]. Neighboring columns interact along [010] to form a herringbone pattern when viewed parallel to [001] (Fig. 3).
Synthesis and crystallization
The synthesis of title compound was previously reported (Calitree et al., 2007). The title compound was dissolved in a solution of ethanol and water (70/30) and recrystallized by slow evaporation to give metallic green prisms suitable for X-ray diffraction.
Refinement
Crystal data, data collection, and .
details are summarized in Table 1Structural data
CCDC reference: 2085596
https://doi.org/10.1107/S2414314621005459/hb4384sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621005459/hb4384Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621005459/hb4384Isup3.cml
Data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C23H23N2Te+·PF6− | F(000) = 1184 |
Mr = 600.00 | Dx = 1.766 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7763 (6) Å | Cell parameters from 9937 reflections |
b = 23.9606 (17) Å | θ = 2.5–30.3° |
c = 10.8738 (8) Å | µ = 1.45 mm−1 |
β = 99.256 (2)° | T = 90 K |
V = 2256.8 (3) Å3 | Plate, metallic green |
Z = 4 | 0.6 × 0.5 × 0.05 mm |
Bruker APEXII CCD diffractometer | 6766 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.071 |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | θmax = 33.0°, θmin = 1.7° |
Tmin = 0.689, Tmax = 0.746 | h = −13→12 |
56521 measured reflections | k = −36→36 |
8157 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0237P)2 + 2.0434P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.005 |
8157 reflections | Δρmax = 0.67 e Å−3 |
302 parameters | Δρmin = −0.59 e Å−3 |
0 restraints |
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 | ||
Te1 | 0.37770 (2) | 0.57306 (2) | 0.60576 (2) | 0.01836 (4) | |
P1 | 0.20110 (7) | 0.81612 (2) | 0.40997 (5) | 0.02187 (11) | |
F3 | 0.1105 (2) | 0.77039 (8) | 0.32013 (17) | 0.0596 (6) | |
F4 | 0.3481 (2) | 0.80903 (9) | 0.34268 (19) | 0.0567 (5) | |
N2 | 0.6606 (2) | 0.74434 (7) | 0.42304 (17) | 0.0210 (3) | |
F5 | 0.2897 (2) | 0.86218 (8) | 0.49805 (18) | 0.0576 (5) | |
F2 | 0.0542 (2) | 0.82231 (11) | 0.47618 (17) | 0.0693 (7) | |
F1 | 0.1372 (3) | 0.86213 (8) | 0.30973 (18) | 0.0595 (5) | |
F6 | 0.2649 (3) | 0.77015 (8) | 0.50973 (19) | 0.0644 (6) | |
N1 | 0.0763 (2) | 0.37834 (8) | 0.56622 (18) | 0.0248 (4) | |
C13 | 0.2664 (2) | 0.50923 (8) | 0.49838 (18) | 0.0164 (3) | |
C7 | 0.3079 (2) | 0.55013 (8) | 0.29042 (18) | 0.0156 (3) | |
C1 | 0.4416 (2) | 0.61632 (8) | 0.45709 (17) | 0.0156 (3) | |
C6 | 0.4000 (2) | 0.59734 (8) | 0.33084 (18) | 0.0155 (3) | |
C5 | 0.4606 (2) | 0.63079 (8) | 0.24046 (19) | 0.0189 (4) | |
H5 | 0.441068 | 0.619248 | 0.155810 | 0.023* | |
C12 | 0.2101 (2) | 0.46640 (8) | 0.56335 (19) | 0.0191 (4) | |
H12 | 0.225645 | 0.467975 | 0.651777 | 0.023* | |
C11 | 0.1301 (2) | 0.42024 (8) | 0.5026 (2) | 0.0190 (4) | |
C19 | 0.1629 (2) | 0.57900 (8) | 0.08336 (19) | 0.0188 (4) | |
H19 | 0.119627 | 0.608620 | 0.124457 | 0.023* | |
C18 | 0.2679 (2) | 0.54247 (8) | 0.15202 (17) | 0.0154 (3) | |
C4 | 0.5441 (2) | 0.67792 (9) | 0.26909 (19) | 0.0199 (4) | |
H4 | 0.580399 | 0.698301 | 0.204645 | 0.024* | |
C3 | 0.5786 (2) | 0.69747 (8) | 0.39471 (19) | 0.0171 (4) | |
C9 | 0.1639 (2) | 0.46274 (9) | 0.30664 (19) | 0.0207 (4) | |
H9 | 0.145827 | 0.461284 | 0.218177 | 0.025* | |
C8 | 0.2473 (2) | 0.50933 (8) | 0.36550 (18) | 0.0163 (3) | |
C2 | 0.5249 (2) | 0.66452 (8) | 0.48724 (19) | 0.0186 (4) | |
H2 | 0.546799 | 0.675927 | 0.571915 | 0.022* | |
C10 | 0.1088 (3) | 0.42026 (9) | 0.3704 (2) | 0.0231 (4) | |
H10 | 0.055233 | 0.390205 | 0.325641 | 0.028* | |
C20 | 0.1214 (3) | 0.57237 (9) | −0.04422 (19) | 0.0212 (4) | |
H20 | 0.049254 | 0.597224 | −0.090058 | 0.025* | |
C23 | 0.3309 (2) | 0.49957 (9) | 0.08981 (19) | 0.0195 (4) | |
H23 | 0.402725 | 0.474487 | 0.135230 | 0.023* | |
C22 | 0.2894 (3) | 0.49323 (9) | −0.0381 (2) | 0.0229 (4) | |
H22 | 0.332861 | 0.463846 | −0.079840 | 0.027* | |
C17 | 0.7068 (3) | 0.77967 (9) | 0.3255 (2) | 0.0259 (4) | |
H17A | 0.758035 | 0.756767 | 0.269628 | 0.039* | |
H17B | 0.778070 | 0.808576 | 0.363729 | 0.039* | |
H17C | 0.615117 | 0.797316 | 0.277811 | 0.039* | |
C16 | 0.6824 (3) | 0.76688 (10) | 0.5492 (2) | 0.0278 (5) | |
H16A | 0.582395 | 0.778526 | 0.569750 | 0.042* | |
H16B | 0.751810 | 0.799123 | 0.554501 | 0.042* | |
H16C | 0.727487 | 0.738145 | 0.608176 | 0.042* | |
C21 | 0.1849 (3) | 0.52966 (9) | −0.10492 (19) | 0.0224 (4) | |
H21 | 0.156722 | 0.525308 | −0.192469 | 0.027* | |
C15 | 0.0866 (3) | 0.38130 (10) | 0.7010 (2) | 0.0307 (5) | |
H15A | 0.195362 | 0.381323 | 0.739952 | 0.046* | |
H15B | 0.034410 | 0.348939 | 0.730416 | 0.046* | |
H15C | 0.036942 | 0.415640 | 0.723435 | 0.046* | |
C14 | 0.0003 (3) | 0.32985 (10) | 0.5022 (3) | 0.0327 (5) | |
H14A | −0.104010 | 0.340189 | 0.462121 | 0.049* | |
H14B | −0.006029 | 0.299921 | 0.562561 | 0.049* | |
H14C | 0.059824 | 0.316883 | 0.438780 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Te1 | 0.02524 (7) | 0.01836 (7) | 0.01140 (6) | −0.00151 (5) | 0.00277 (5) | 0.00012 (4) |
P1 | 0.0231 (3) | 0.0232 (3) | 0.0192 (3) | −0.0027 (2) | 0.0032 (2) | 0.0013 (2) |
F3 | 0.0821 (14) | 0.0652 (12) | 0.0340 (9) | −0.0458 (11) | 0.0166 (9) | −0.0173 (9) |
F4 | 0.0367 (9) | 0.0773 (14) | 0.0610 (12) | 0.0056 (9) | 0.0226 (9) | −0.0010 (10) |
N2 | 0.0213 (8) | 0.0186 (8) | 0.0219 (9) | −0.0039 (6) | 0.0003 (7) | −0.0002 (7) |
F5 | 0.0738 (13) | 0.0491 (11) | 0.0467 (11) | −0.0247 (10) | −0.0002 (10) | −0.0150 (9) |
F2 | 0.0339 (9) | 0.146 (2) | 0.0308 (9) | −0.0007 (11) | 0.0147 (7) | −0.0149 (11) |
F1 | 0.0782 (14) | 0.0536 (11) | 0.0438 (10) | 0.0231 (10) | 0.0010 (10) | 0.0201 (9) |
F6 | 0.0841 (15) | 0.0490 (11) | 0.0559 (12) | 0.0037 (10) | −0.0014 (11) | 0.0296 (9) |
N1 | 0.0276 (9) | 0.0207 (8) | 0.0274 (9) | −0.0028 (7) | 0.0082 (8) | 0.0048 (7) |
C13 | 0.0176 (8) | 0.0161 (8) | 0.0159 (8) | 0.0018 (7) | 0.0036 (7) | −0.0004 (7) |
C7 | 0.0162 (8) | 0.0173 (8) | 0.0130 (8) | 0.0011 (7) | 0.0015 (7) | 0.0000 (7) |
C1 | 0.0171 (8) | 0.0174 (8) | 0.0123 (8) | 0.0022 (7) | 0.0026 (7) | 0.0021 (6) |
C6 | 0.0154 (8) | 0.0172 (8) | 0.0136 (8) | 0.0009 (7) | 0.0016 (7) | 0.0003 (7) |
C5 | 0.0201 (9) | 0.0219 (9) | 0.0150 (9) | −0.0005 (7) | 0.0041 (7) | −0.0002 (7) |
C12 | 0.0235 (9) | 0.0189 (9) | 0.0156 (9) | 0.0030 (7) | 0.0052 (7) | 0.0013 (7) |
C11 | 0.0198 (9) | 0.0166 (9) | 0.0211 (9) | 0.0011 (7) | 0.0050 (7) | 0.0030 (7) |
C19 | 0.0217 (9) | 0.0191 (9) | 0.0157 (9) | 0.0019 (7) | 0.0030 (7) | 0.0011 (7) |
C18 | 0.0169 (8) | 0.0164 (8) | 0.0130 (8) | −0.0024 (7) | 0.0024 (7) | 0.0002 (6) |
C4 | 0.0212 (9) | 0.0218 (9) | 0.0166 (9) | −0.0026 (7) | 0.0032 (7) | 0.0011 (7) |
C3 | 0.0156 (8) | 0.0166 (8) | 0.0186 (9) | 0.0010 (7) | 0.0016 (7) | 0.0003 (7) |
C9 | 0.0233 (10) | 0.0236 (10) | 0.0146 (9) | −0.0043 (8) | 0.0010 (7) | −0.0005 (7) |
C8 | 0.0167 (8) | 0.0166 (8) | 0.0155 (8) | 0.0004 (7) | 0.0019 (7) | 0.0005 (7) |
C2 | 0.0223 (9) | 0.0181 (9) | 0.0149 (8) | 0.0000 (7) | 0.0018 (7) | −0.0011 (7) |
C10 | 0.0268 (11) | 0.0212 (10) | 0.0209 (10) | −0.0062 (8) | 0.0024 (8) | −0.0010 (8) |
C20 | 0.0225 (10) | 0.0251 (10) | 0.0156 (9) | 0.0014 (8) | 0.0018 (7) | 0.0031 (7) |
C23 | 0.0207 (9) | 0.0198 (9) | 0.0179 (9) | 0.0024 (7) | 0.0029 (7) | 0.0000 (7) |
C22 | 0.0241 (10) | 0.0252 (10) | 0.0199 (10) | 0.0004 (8) | 0.0052 (8) | −0.0069 (8) |
C17 | 0.0277 (11) | 0.0231 (10) | 0.0272 (11) | −0.0077 (8) | 0.0056 (9) | 0.0013 (9) |
C16 | 0.0341 (12) | 0.0243 (10) | 0.0239 (11) | −0.0074 (9) | 0.0012 (9) | −0.0056 (8) |
C21 | 0.0242 (10) | 0.0304 (11) | 0.0125 (9) | −0.0024 (8) | 0.0022 (7) | −0.0024 (8) |
C15 | 0.0397 (13) | 0.0275 (11) | 0.0291 (12) | 0.0046 (10) | 0.0188 (10) | 0.0083 (9) |
C14 | 0.0342 (12) | 0.0215 (10) | 0.0410 (14) | −0.0079 (9) | 0.0015 (11) | 0.0078 (10) |
Te1—C13 | 2.0711 (19) | C19—C20 | 1.386 (3) |
Te1—C1 | 2.0723 (19) | C18—C23 | 1.393 (3) |
P1—F3 | 1.5930 (17) | C4—H4 | 0.9500 |
P1—F4 | 1.5911 (18) | C4—C3 | 1.430 (3) |
P1—F5 | 1.5813 (17) | C3—C2 | 1.418 (3) |
P1—F2 | 1.5816 (18) | C9—H9 | 0.9500 |
P1—F1 | 1.5877 (17) | C9—C8 | 1.429 (3) |
P1—F6 | 1.5838 (18) | C9—C10 | 1.363 (3) |
N2—C3 | 1.343 (3) | C2—H2 | 0.9500 |
N2—C17 | 1.464 (3) | C10—H10 | 0.9500 |
N2—C16 | 1.458 (3) | C20—H20 | 0.9500 |
N1—C11 | 1.347 (3) | C20—C21 | 1.382 (3) |
N1—C15 | 1.456 (3) | C23—H23 | 0.9500 |
N1—C14 | 1.460 (3) | C23—C22 | 1.388 (3) |
C13—C12 | 1.382 (3) | C22—H22 | 0.9500 |
C13—C8 | 1.428 (3) | C22—C21 | 1.385 (3) |
C7—C6 | 1.419 (3) | C17—H17A | 0.9800 |
C7—C18 | 1.501 (3) | C17—H17B | 0.9800 |
C7—C8 | 1.430 (3) | C17—H17C | 0.9800 |
C1—C6 | 1.436 (3) | C16—H16A | 0.9800 |
C1—C2 | 1.378 (3) | C16—H16B | 0.9800 |
C6—C5 | 1.435 (3) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | C21—H21 | 0.9500 |
C5—C4 | 1.355 (3) | C15—H15A | 0.9800 |
C12—H12 | 0.9500 | C15—H15B | 0.9800 |
C12—C11 | 1.416 (3) | C15—H15C | 0.9800 |
C11—C10 | 1.419 (3) | C14—H14A | 0.9800 |
C19—H19 | 0.9500 | C14—H14B | 0.9800 |
C19—C18 | 1.397 (3) | C14—H14C | 0.9800 |
C13—Te1—C1 | 95.27 (8) | N2—C3—C4 | 121.10 (19) |
F4—P1—F3 | 90.36 (11) | N2—C3—C2 | 122.01 (18) |
F5—P1—F3 | 179.21 (12) | C2—C3—C4 | 116.88 (18) |
F5—P1—F4 | 89.82 (11) | C8—C9—H9 | 118.2 |
F5—P1—F2 | 90.94 (12) | C10—C9—H9 | 118.2 |
F5—P1—F1 | 90.93 (11) | C10—C9—C8 | 123.63 (19) |
F5—P1—F6 | 89.14 (11) | C13—C8—C7 | 125.81 (18) |
F2—P1—F3 | 88.88 (11) | C13—C8—C9 | 114.86 (17) |
F2—P1—F4 | 179.18 (13) | C9—C8—C7 | 119.29 (18) |
F2—P1—F1 | 91.36 (12) | C1—C2—C3 | 121.47 (18) |
F2—P1—F6 | 88.73 (12) | C1—C2—H2 | 119.3 |
F1—P1—F3 | 88.30 (12) | C3—C2—H2 | 119.3 |
F1—P1—F4 | 88.93 (11) | C11—C10—H10 | 119.5 |
F6—P1—F3 | 91.63 (12) | C9—C10—C11 | 121.0 (2) |
F6—P1—F4 | 90.98 (12) | C9—C10—H10 | 119.5 |
F6—P1—F1 | 179.88 (14) | C19—C20—H20 | 119.9 |
C3—N2—C17 | 121.19 (18) | C21—C20—C19 | 120.11 (19) |
C3—N2—C16 | 120.66 (18) | C21—C20—H20 | 119.9 |
C16—N2—C17 | 117.25 (17) | C18—C23—H23 | 119.8 |
C11—N1—C15 | 120.73 (19) | C22—C23—C18 | 120.46 (19) |
C11—N1—C14 | 121.3 (2) | C22—C23—H23 | 119.8 |
C15—N1—C14 | 117.96 (19) | C23—C22—H22 | 120.0 |
C12—C13—Te1 | 115.80 (14) | C21—C22—C23 | 120.09 (19) |
C12—C13—C8 | 121.69 (18) | C21—C22—H22 | 120.0 |
C8—C13—Te1 | 122.50 (14) | N2—C17—H17A | 109.5 |
C6—C7—C18 | 115.97 (16) | N2—C17—H17B | 109.5 |
C6—C7—C8 | 127.88 (18) | N2—C17—H17C | 109.5 |
C8—C7—C18 | 116.15 (17) | H17A—C17—H17B | 109.5 |
C6—C1—Te1 | 121.88 (14) | H17A—C17—H17C | 109.5 |
C2—C1—Te1 | 115.68 (14) | H17B—C17—H17C | 109.5 |
C2—C1—C6 | 122.44 (18) | N2—C16—H16A | 109.5 |
C7—C6—C1 | 126.39 (17) | N2—C16—H16B | 109.5 |
C7—C6—C5 | 119.26 (17) | N2—C16—H16C | 109.5 |
C5—C6—C1 | 114.35 (17) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 118.2 | H16A—C16—H16C | 109.5 |
C4—C5—C6 | 123.68 (19) | H16B—C16—H16C | 109.5 |
C4—C5—H5 | 118.2 | C20—C21—C22 | 120.00 (19) |
C13—C12—H12 | 118.9 | C20—C21—H21 | 120.0 |
C13—C12—C11 | 122.21 (19) | C22—C21—H21 | 120.0 |
C11—C12—H12 | 118.9 | N1—C15—H15A | 109.5 |
N1—C11—C12 | 122.1 (2) | N1—C15—H15B | 109.5 |
N1—C11—C10 | 121.37 (19) | N1—C15—H15C | 109.5 |
C12—C11—C10 | 116.57 (18) | H15A—C15—H15B | 109.5 |
C18—C19—H19 | 119.7 | H15A—C15—H15C | 109.5 |
C20—C19—H19 | 119.7 | H15B—C15—H15C | 109.5 |
C20—C19—C18 | 120.53 (19) | N1—C14—H14A | 109.5 |
C19—C18—C7 | 119.16 (17) | N1—C14—H14B | 109.5 |
C23—C18—C7 | 122.02 (17) | N1—C14—H14C | 109.5 |
C23—C18—C19 | 118.82 (18) | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 119.5 | H14A—C14—H14C | 109.5 |
C5—C4—C3 | 121.07 (19) | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 119.5 | ||
Te1—C13—C12—C11 | 179.33 (15) | C18—C7—C6—C5 | −6.0 (3) |
Te1—C13—C8—C7 | 3.9 (3) | C18—C7—C8—C13 | −177.95 (18) |
Te1—C13—C8—C9 | −178.28 (14) | C18—C7—C8—C9 | 4.3 (3) |
Te1—C1—C6—C7 | 3.0 (3) | C18—C19—C20—C21 | −0.5 (3) |
Te1—C1—C6—C5 | −176.93 (13) | C18—C23—C22—C21 | 0.0 (3) |
Te1—C1—C2—C3 | 178.68 (15) | C4—C3—C2—C1 | −0.9 (3) |
N2—C3—C2—C1 | −179.61 (19) | C8—C13—C12—C11 | −0.2 (3) |
N1—C11—C10—C9 | −179.8 (2) | C8—C7—C6—C1 | −5.3 (3) |
C13—C12—C11—N1 | 179.5 (2) | C8—C7—C6—C5 | 174.64 (19) |
C13—C12—C11—C10 | −0.6 (3) | C8—C7—C18—C19 | 108.2 (2) |
C7—C6—C5—C4 | 177.11 (19) | C8—C7—C18—C23 | −71.0 (2) |
C7—C18—C23—C22 | 179.00 (19) | C8—C9—C10—C11 | 0.8 (3) |
C1—C6—C5—C4 | −3.0 (3) | C2—C1—C6—C7 | −176.38 (19) |
C6—C7—C18—C19 | −71.2 (2) | C2—C1—C6—C5 | 3.7 (3) |
C6—C7—C18—C23 | 109.6 (2) | C10—C9—C8—C13 | −1.5 (3) |
C6—C7—C8—C13 | 1.4 (3) | C10—C9—C8—C7 | 176.5 (2) |
C6—C7—C8—C9 | −176.38 (19) | C20—C19—C18—C7 | −178.77 (19) |
C6—C1—C2—C3 | −1.9 (3) | C20—C19—C18—C23 | 0.5 (3) |
C6—C5—C4—C3 | 0.4 (3) | C23—C22—C21—C20 | −0.1 (3) |
C5—C4—C3—N2 | −179.61 (19) | C17—N2—C3—C4 | 5.2 (3) |
C5—C4—C3—C2 | 1.6 (3) | C17—N2—C3—C2 | −176.13 (19) |
C12—C13—C8—C7 | −176.66 (19) | C16—N2—C3—C4 | 174.0 (2) |
C12—C13—C8—C9 | 1.2 (3) | C16—N2—C3—C2 | −7.3 (3) |
C12—C11—C10—C9 | 0.3 (3) | C15—N1—C11—C12 | 5.5 (3) |
C19—C18—C23—C22 | −0.2 (3) | C15—N1—C11—C10 | −174.4 (2) |
C19—C20—C21—C22 | 0.4 (3) | C14—N1—C11—C12 | −177.2 (2) |
C18—C7—C6—C1 | 174.05 (18) | C14—N1—C11—C10 | 3.0 (3) |
Funding information
Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. DMR-2003932).
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