organic compounds
Ethyl 3-amino-2-cyano-4-(4-methoxyphenyl)-6- methylthieno[2,3-b]pyridine-5-carboxylate
aChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and fDepartment of Chemistry, Faculty of Science, Sana'a University, Yemen
*Correspondence e-mail: s.mohamed@mmu.ac.uk
In the title molecule, C19H17N3O3S, the bicyclic core is planar [maximum deviation = 0.0205 (1) Å] In the crystal, the molecules stack along the a-axis direction through π–π-stacking interactions between the bicyclic units with a small alternation in the interplanar distances along the stack. The stacks are held together by N—H⋯N and C—H⋯O hydrogen bonds. The carboethoxy substituent is disordered over several closely spaced sites and was modeled as having two-component disorder [occupancy ratio 0.548 (16):0.452 (16)]. The final was as a two-component twin.
CCDC reference: 1585896
Structure description
The spectrum of biological activities of thienopyridine derivatives is rather broad and includes antiviral (Schnute et al., 2007; Attaby et al., 2007), antidiabetic (Bahekar et al. 2007), antimicrobial (Abdel-Rahman et al., 2003; Hussein et al. 2000), anti-inflammatory (Madhusudana et al., 2012), antihypertensive (Ribichini et al., 2007), antitumor (Hayakawa et al., 2004), and neurotropic activities (Krauze et al., 1999). As part of our studies in this area, we undertook the synthesis and of the title compound (Fig. 1).
As expected, the bicyclic unit is planar [maximum deviations of −0.0151 (1) and 0.0205 (1) Å for atoms C1 and C6, respectively] while the dihedral angle between the mean planes of the C1/C2/C3/N3/C4/C7 unit and the C8–C13 ring is 65.71 (17)°. In the crystal, the molecules stack in a head-to-tail fashion along the a-axis direction through π–π-stacking interactions between the bicyclic units with the centroid–centroid distances alternating between 3.693 (2) and 3.637 (2) Å along the stack (Fig. 2). The stacks are associated along the a-axis direction by pairwise N2—H2B⋯N1i [symmetry code: (i) −x, −y + 2, −z + 2] hydrogen bonds and along the c-axis direction by pairwise C10—H10⋯O1ii [symmetry code: (ii) −x + 1, −y + 2, −z + 1] hydrogen bonds (Table 1 and Fig. 3).
Synthesis and crystallization
The title compound was prepared by heating equimolar quantities of 5-ethoxycarbonyl-3-cyano-6-methyl-4-(4-methoxyphenyl)pyridine-2(1H)-thione (3.284 g; 10 mmol) and chloroacetonitrile (0.76 g; 10 mmol) in absolute ethanol (30 ml) containing dissolved sodium (0.50 g) under reflux for 20 min. The solid that formed on cooling was collected by filtration and recrystallized from ethanol solution as yellow crystals of the title compound. Yield: 90%, m.p.: 457–458 K.
IR (KBr) cm−1: 3476, 3342 (NH2); 2976 (C—H, aliphatic); 2199 (C≡N); 1729 (C=O); 1H NMR (400 MHz, CDCl3) p.p.m.: 7.27–7.30 (dd, J = 2.4 Hz, 2H, Ar—H), 7.00–7.03 (dd, J = 2.4 Hz, 2H, Ar—H), 4.32 (s, 2H, NH2), 4.01–4.06 (q, J = 7.0 Hz, 2H, OCH2), 3.88 (s, 3H, OCH3), 2.67 (s, 3H, CH3), 0.99–1.03 (t, J = 7.2 Hz, 3H, CH3 of ester); 13C NMR (100 MHz, CDCl3) p.p.m.: 167.5, 161.3, 160.6, 156.3, 149.3, 143.8, 130.0 (CH), 127.6, 125.4, 118.5, 114.7, 114.1 (CH),61.6 (OCH2), 55.4 (OCH3), 23.1 (CH3 at C-6), 13.8 (CH3 of ester group). MS: m/z 367 (M+, 100%), 339 (M±CO, 10%), 322 (M±OEt, 15%), 321 (M± EtOH, 15%). Analysis calculated for C19H17N3O3S (367.1): C, 62.11; H, 4.66; N, 11.44; S, 8.73%. Found: C, 62.00; H, 4.70; N, 11.83; S, 9.02%.
Refinement
Crystal data, data collection and structure . The carboethoxy substituent is disordered over several closely spaced sites and was modeled as having two-component disorder with the disordered atoms lightly restrained with ISOR instructions [occupancy ratio 0.548 (16):0.452 (16)]. Geometrical restraints were also imposed to make the geometries of the two components comparable. The final was as a two-component twin with a 0.945 (7):0.055 (7) domain ratio.
details are summarized in Table 2Structural data
CCDC reference: 1585896
https://doi.org/10.1107/S2414314617016509/hg4031sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016509/hg4031Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016509/hg4031Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C19H17N3O3S | Z = 2 |
Mr = 367.41 | F(000) = 384 |
Triclinic, P1 | Dx = 1.322 Mg m−3 |
a = 7.2713 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 11.3575 (3) Å | Cell parameters from 7181 reflections |
c = 12.7769 (4) Å | θ = 6.7–72.3° |
α = 67.004 (1)° | µ = 1.76 mm−1 |
β = 79.649 (1)° | T = 225 K |
γ = 72.217 (1)° | Plate, yellow |
V = 922.71 (5) Å3 | 0.22 × 0.15 × 0.07 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 13203 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 8440 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.039 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.3°, θmin = 3.8° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −14→14 |
Tmin = 0.70, Tmax = 0.89 | l = −15→15 |
13203 measured reflections |
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)] = 0.067 | Hydrogen site location: mixed |
wR(F2) = 0.210 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0917P)2 + 0.306P] where P = (Fo2 + 2Fc2)/3 |
13203 reflections | (Δ/σ)max = 0.002 |
250 parameters | Δρmax = 0.72 e Å−3 |
31 restraints | Δρmin = −0.75 e Å−3 |
Experimental. Analysis of 887 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about the b* axis. The raw data were processed using the multi- component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
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. |
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 > 2sigma(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. The carboethoxy substituent is disordered over several closely spaced sites and was modeled as a 2-component disorder with the disordered atoms lightly restrained with ISOR instructions. Geometrical restraints were also imposed to make the geometries of the two components comparable. The final refinement was as a 2-component twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.17612 (11) | 0.52232 (7) | 1.16443 (7) | 0.0422 (3) | |
O1 | 0.3137 (5) | 0.9605 (3) | 0.4124 (2) | 0.0686 (8) | |
O2 | 0.5748 (13) | 0.391 (2) | 0.7012 (18) | 0.063 (4) | 0.452 (16) |
O3 | 0.280 (3) | 0.367 (5) | 0.708 (2) | 0.0726 (11) | 0.452 (16) |
O2A | 0.5864 (11) | 0.3522 (19) | 0.7172 (15) | 0.063 (4) | 0.548 (16) |
O3A | 0.276 (2) | 0.364 (4) | 0.714 (2) | 0.0726 (11) | 0.548 (16) |
N1 | 0.0048 (6) | 0.8833 (3) | 1.1436 (3) | 0.0732 (10) | |
N2 | 0.1236 (5) | 0.8287 (3) | 0.8772 (3) | 0.0589 (8) | |
H2A | 0.1775 | 0.8439 | 0.8046 | 0.071* | |
H2B | 0.0903 | 0.9056 | 0.8909 | 0.071* | |
N3 | 0.3041 (4) | 0.3476 (2) | 1.0592 (2) | 0.0395 (6) | |
C1 | 0.2904 (4) | 0.5543 (3) | 0.8421 (3) | 0.0364 (6) | |
C2 | 0.3499 (4) | 0.4209 (3) | 0.8549 (3) | 0.0383 (7) | |
C3 | 0.3555 (4) | 0.3206 (3) | 0.9638 (3) | 0.0398 (7) | |
C4 | 0.2451 (4) | 0.4757 (3) | 1.0464 (3) | 0.0355 (6) | |
C5 | 0.1273 (4) | 0.6884 (3) | 1.0750 (3) | 0.0411 (7) | |
C6 | 0.1604 (4) | 0.7082 (3) | 0.9608 (3) | 0.0391 (7) | |
C7 | 0.2347 (4) | 0.5831 (3) | 0.9426 (2) | 0.0346 (6) | |
C8 | 0.2925 (4) | 0.6600 (3) | 0.7277 (3) | 0.0391 (7) | |
C9 | 0.4199 (5) | 0.7398 (3) | 0.6993 (3) | 0.0471 (8) | |
H9 | 0.5054 | 0.7255 | 0.7527 | 0.056* | |
C10 | 0.4226 (6) | 0.8388 (3) | 0.5946 (3) | 0.0520 (8) | |
H10 | 0.5085 | 0.8922 | 0.5773 | 0.062* | |
C11 | 0.2981 (6) | 0.8604 (3) | 0.5139 (3) | 0.0510 (8) | |
C12 | 0.1734 (6) | 0.7819 (4) | 0.5398 (3) | 0.0537 (9) | |
H12 | 0.0896 | 0.7955 | 0.4857 | 0.064* | |
C13 | 0.1712 (5) | 0.6822 (3) | 0.6461 (3) | 0.0481 (8) | |
H13 | 0.0856 | 0.6287 | 0.6630 | 0.058* | |
C14 | 0.1925 (8) | 0.9851 (6) | 0.3254 (4) | 0.0799 (13) | |
H14A | 0.2187 | 0.9060 | 0.3071 | 0.120* | |
H14B | 0.2190 | 1.0574 | 0.2578 | 0.120* | |
H14C | 0.0577 | 1.0085 | 0.3524 | 0.120* | |
C15 | 0.4197 (5) | 0.3826 (3) | 0.7514 (3) | 0.0453 (7) | |
C16 | 0.319 (2) | 0.3661 (19) | 0.5911 (15) | 0.075 (3) | 0.452 (16) |
H16A | 0.3679 | 0.4421 | 0.5406 | 0.090* | 0.452 (16) |
H16B | 0.4162 | 0.2849 | 0.5901 | 0.090* | 0.452 (16) |
C17 | 0.154 (3) | 0.372 (3) | 0.5549 (19) | 0.122 (5) | 0.452 (16) |
H17A | 0.1770 | 0.3714 | 0.4779 | 0.183* | 0.452 (16) |
H17B | 0.1063 | 0.2963 | 0.6049 | 0.183* | 0.452 (16) |
H17C | 0.0583 | 0.4530 | 0.5555 | 0.183* | 0.452 (16) |
C16A | 0.3287 (18) | 0.3101 (15) | 0.6216 (13) | 0.075 (3) | 0.548 (16) |
H16C | 0.3799 | 0.3740 | 0.5548 | 0.090* | 0.548 (16) |
H16D | 0.4338 | 0.2290 | 0.6459 | 0.090* | 0.548 (16) |
C17A | 0.188 (2) | 0.282 (2) | 0.5890 (16) | 0.122 (5) | 0.548 (16) |
H17D | 0.2394 | 0.2471 | 0.5283 | 0.183* | 0.548 (16) |
H17E | 0.1385 | 0.2159 | 0.6533 | 0.183* | 0.548 (16) |
H17F | 0.0844 | 0.3615 | 0.5619 | 0.183* | 0.548 (16) |
C18 | 0.4230 (6) | 0.1760 (3) | 0.9794 (3) | 0.0541 (9) | |
H18A | 0.4865 | 0.1265 | 1.0501 | 0.081* | |
H18B | 0.5135 | 0.1645 | 0.9162 | 0.081* | |
H18C | 0.3126 | 0.1437 | 0.9819 | 0.081* | |
C19 | 0.0588 (5) | 0.7929 (3) | 1.1170 (3) | 0.0493 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0488 (5) | 0.0409 (4) | 0.0407 (5) | −0.0131 (3) | −0.0006 (3) | −0.0187 (3) |
O1 | 0.097 (2) | 0.0602 (15) | 0.0456 (15) | −0.0313 (14) | −0.0267 (14) | 0.0022 (12) |
O2 | 0.0553 (18) | 0.080 (11) | 0.073 (5) | −0.018 (3) | 0.004 (2) | −0.052 (7) |
O3 | 0.0555 (16) | 0.114 (3) | 0.085 (3) | −0.0209 (15) | −0.0008 (14) | −0.076 (3) |
O2A | 0.0553 (18) | 0.080 (11) | 0.073 (5) | −0.018 (3) | 0.004 (2) | −0.052 (7) |
O3A | 0.0555 (16) | 0.114 (3) | 0.085 (3) | −0.0209 (15) | −0.0008 (14) | −0.076 (3) |
N1 | 0.104 (3) | 0.0515 (18) | 0.070 (2) | −0.0031 (17) | −0.0112 (19) | −0.0381 (17) |
N2 | 0.092 (2) | 0.0312 (13) | 0.0486 (17) | 0.0031 (13) | −0.0180 (15) | −0.0174 (12) |
N3 | 0.0427 (13) | 0.0327 (12) | 0.0458 (15) | −0.0105 (9) | −0.0064 (11) | −0.0148 (11) |
C1 | 0.0378 (14) | 0.0341 (14) | 0.0409 (17) | −0.0071 (10) | −0.0095 (12) | −0.0161 (12) |
C2 | 0.0399 (14) | 0.0359 (14) | 0.0456 (18) | −0.0081 (11) | −0.0073 (12) | −0.0209 (13) |
C3 | 0.0403 (15) | 0.0334 (14) | 0.0505 (19) | −0.0090 (11) | −0.0072 (13) | −0.0189 (13) |
C4 | 0.0323 (13) | 0.0362 (14) | 0.0431 (17) | −0.0094 (10) | −0.0061 (11) | −0.0177 (13) |
C5 | 0.0417 (15) | 0.0393 (15) | 0.0480 (18) | −0.0065 (11) | −0.0056 (13) | −0.0236 (14) |
C6 | 0.0410 (15) | 0.0334 (14) | 0.0467 (18) | −0.0035 (11) | −0.0113 (12) | −0.0193 (13) |
C7 | 0.0354 (14) | 0.0307 (13) | 0.0409 (16) | −0.0055 (10) | −0.0093 (12) | −0.0156 (12) |
C8 | 0.0476 (16) | 0.0341 (14) | 0.0388 (17) | −0.0078 (11) | −0.0084 (12) | −0.0163 (13) |
C9 | 0.0596 (19) | 0.0383 (15) | 0.0479 (19) | −0.0138 (13) | −0.0211 (15) | −0.0121 (14) |
C10 | 0.067 (2) | 0.0438 (17) | 0.049 (2) | −0.0234 (15) | −0.0174 (16) | −0.0078 (15) |
C11 | 0.068 (2) | 0.0427 (16) | 0.043 (2) | −0.0153 (14) | −0.0152 (16) | −0.0105 (15) |
C12 | 0.062 (2) | 0.060 (2) | 0.0431 (19) | −0.0180 (16) | −0.0187 (16) | −0.0156 (16) |
C13 | 0.0539 (18) | 0.0524 (18) | 0.0455 (19) | −0.0200 (14) | −0.0100 (14) | −0.0181 (16) |
C14 | 0.093 (3) | 0.091 (3) | 0.047 (2) | −0.025 (3) | −0.028 (2) | −0.005 (2) |
C15 | 0.0479 (18) | 0.0439 (16) | 0.053 (2) | −0.0080 (12) | −0.0068 (14) | −0.0283 (15) |
C16 | 0.082 (3) | 0.095 (7) | 0.077 (6) | −0.019 (5) | −0.007 (3) | −0.063 (6) |
C17 | 0.131 (7) | 0.178 (12) | 0.111 (8) | −0.054 (9) | −0.007 (5) | −0.098 (10) |
C16A | 0.082 (3) | 0.095 (7) | 0.077 (6) | −0.019 (5) | −0.007 (3) | −0.063 (6) |
C17A | 0.131 (7) | 0.178 (12) | 0.111 (8) | −0.054 (9) | −0.007 (5) | −0.098 (10) |
C18 | 0.070 (2) | 0.0325 (15) | 0.060 (2) | −0.0087 (14) | −0.0082 (17) | −0.0188 (15) |
C19 | 0.0590 (19) | 0.0446 (17) | 0.048 (2) | −0.0074 (14) | −0.0069 (15) | −0.0242 (15) |
S1—C4 | 1.731 (3) | C8—C9 | 1.395 (5) |
S1—C5 | 1.744 (3) | C9—C10 | 1.372 (5) |
O1—C11 | 1.364 (4) | C9—H9 | 0.9400 |
O1—C14 | 1.431 (5) | C10—C11 | 1.395 (5) |
O2—C15 | 1.204 (6) | C10—H10 | 0.9400 |
O3—C15 | 1.321 (5) | C11—C12 | 1.372 (5) |
O3—C16 | 1.479 (10) | C12—C13 | 1.388 (5) |
O2A—C15 | 1.204 (6) | C12—H12 | 0.9400 |
O3A—C15 | 1.320 (5) | C13—H13 | 0.9400 |
O3A—C16A | 1.479 (10) | C14—H14A | 0.9700 |
N1—C19 | 1.142 (5) | C14—H14B | 0.9700 |
N2—C6 | 1.350 (4) | C14—H14C | 0.9700 |
N2—H2A | 0.9099 | C16—C17 | 1.333 (11) |
N2—H2B | 0.9100 | C16—H16A | 0.9800 |
N3—C3 | 1.333 (4) | C16—H16B | 0.9800 |
N3—C4 | 1.336 (4) | C17—H17A | 0.9700 |
C1—C2 | 1.393 (4) | C17—H17B | 0.9700 |
C1—C7 | 1.407 (4) | C17—H17C | 0.9700 |
C1—C8 | 1.487 (4) | C16A—C17A | 1.334 (11) |
C2—C3 | 1.410 (5) | C16A—H16C | 0.9800 |
C2—C15 | 1.506 (4) | C16A—H16D | 0.9800 |
C3—C18 | 1.505 (4) | C17A—H17D | 0.9700 |
C4—C7 | 1.403 (4) | C17A—H17E | 0.9700 |
C5—C6 | 1.373 (5) | C17A—H17F | 0.9700 |
C5—C19 | 1.409 (4) | C18—H18A | 0.9700 |
C6—C7 | 1.453 (4) | C18—H18B | 0.9700 |
C8—C13 | 1.385 (4) | C18—H18C | 0.9700 |
C4—S1—C5 | 89.80 (14) | C8—C13—H13 | 119.3 |
C11—O1—C14 | 117.8 (3) | C12—C13—H13 | 119.3 |
C15—O3—C16 | 116.9 (13) | O1—C14—H14A | 109.5 |
C15—O3A—C16A | 116.4 (11) | O1—C14—H14B | 109.5 |
C6—N2—H2A | 123.3 | H14A—C14—H14B | 109.5 |
C6—N2—H2B | 122.9 | O1—C14—H14C | 109.5 |
H2A—N2—H2B | 108.8 | H14A—C14—H14C | 109.5 |
C3—N3—C4 | 116.4 (3) | H14B—C14—H14C | 109.5 |
C2—C1—C7 | 116.7 (3) | O2A—C15—O3A | 123.2 (7) |
C2—C1—C8 | 121.1 (3) | O2—C15—O3 | 123.0 (8) |
C7—C1—C8 | 122.1 (2) | O2—C15—C2 | 122.7 (10) |
C1—C2—C3 | 121.1 (3) | O2A—C15—C2 | 125.5 (8) |
C1—C2—C15 | 119.6 (3) | O3A—C15—C2 | 110.3 (7) |
C3—C2—C15 | 119.2 (3) | O3—C15—C2 | 112.8 (8) |
N3—C3—C2 | 122.3 (3) | C17—C16—O3 | 108.6 (13) |
N3—C3—C18 | 115.9 (3) | C17—C16—H16A | 110.0 |
C2—C3—C18 | 121.8 (3) | O3—C16—H16A | 110.0 |
N3—C4—C7 | 126.0 (3) | C17—C16—H16B | 110.0 |
N3—C4—S1 | 120.4 (2) | O3—C16—H16B | 110.0 |
C7—C4—S1 | 113.6 (2) | H16A—C16—H16B | 108.3 |
C6—C5—C19 | 123.1 (3) | C16—C17—H17A | 109.5 |
C6—C5—S1 | 114.4 (2) | C16—C17—H17B | 109.5 |
C19—C5—S1 | 122.5 (3) | H17A—C17—H17B | 109.5 |
N2—C6—C5 | 124.0 (3) | C16—C17—H17C | 109.5 |
N2—C6—C7 | 124.9 (3) | H17A—C17—H17C | 109.5 |
C5—C6—C7 | 111.2 (3) | H17B—C17—H17C | 109.5 |
C4—C7—C1 | 117.5 (2) | C17A—C16A—O3A | 117.0 (11) |
C4—C7—C6 | 111.0 (3) | C17A—C16A—H16C | 108.1 |
C1—C7—C6 | 131.5 (3) | O3A—C16A—H16C | 108.1 |
C13—C8—C9 | 117.9 (3) | C17A—C16A—H16D | 108.1 |
C13—C8—C1 | 121.9 (3) | O3A—C16A—H16D | 108.1 |
C9—C8—C1 | 120.2 (3) | H16C—C16A—H16D | 107.3 |
C10—C9—C8 | 121.2 (3) | C16A—C17A—H17D | 109.5 |
C10—C9—H9 | 119.4 | C16A—C17A—H17E | 109.5 |
C8—C9—H9 | 119.4 | H17D—C17A—H17E | 109.5 |
C9—C10—C11 | 120.1 (3) | C16A—C17A—H17F | 109.5 |
C9—C10—H10 | 119.9 | H17D—C17A—H17F | 109.5 |
C11—C10—H10 | 119.9 | H17E—C17A—H17F | 109.5 |
O1—C11—C12 | 125.0 (3) | C3—C18—H18A | 109.5 |
O1—C11—C10 | 115.4 (3) | C3—C18—H18B | 109.5 |
C12—C11—C10 | 119.6 (3) | H18A—C18—H18B | 109.5 |
C11—C12—C13 | 119.9 (3) | C3—C18—H18C | 109.5 |
C11—C12—H12 | 120.0 | H18A—C18—H18C | 109.5 |
C13—C12—H12 | 120.0 | H18B—C18—H18C | 109.5 |
C8—C13—C12 | 121.4 (3) | N1—C19—C5 | 175.4 (4) |
C7—C1—C2—C3 | −0.7 (4) | C5—C6—C7—C1 | −179.3 (3) |
C8—C1—C2—C3 | 177.3 (3) | C2—C1—C8—C13 | 66.5 (4) |
C7—C1—C2—C15 | −177.4 (3) | C7—C1—C8—C13 | −115.6 (3) |
C8—C1—C2—C15 | 0.7 (4) | C2—C1—C8—C9 | −113.1 (3) |
C4—N3—C3—C2 | 0.5 (4) | C7—C1—C8—C9 | 64.9 (4) |
C4—N3—C3—C18 | 179.6 (3) | C13—C8—C9—C10 | 1.2 (5) |
C1—C2—C3—N3 | 0.3 (5) | C1—C8—C9—C10 | −179.3 (3) |
C15—C2—C3—N3 | 176.9 (3) | C8—C9—C10—C11 | −0.7 (6) |
C1—C2—C3—C18 | −178.8 (3) | C14—O1—C11—C12 | −0.7 (6) |
C15—C2—C3—C18 | −2.1 (4) | C14—O1—C11—C10 | 178.6 (4) |
C3—N3—C4—C7 | −0.8 (4) | C9—C10—C11—O1 | −179.4 (3) |
C3—N3—C4—S1 | −179.6 (2) | C9—C10—C11—C12 | −0.1 (6) |
C5—S1—C4—N3 | −179.9 (3) | O1—C11—C12—C13 | 179.6 (4) |
C5—S1—C4—C7 | 1.1 (2) | C10—C11—C12—C13 | 0.4 (6) |
C4—S1—C5—C6 | 0.3 (2) | C9—C8—C13—C12 | −1.0 (5) |
C4—S1—C5—C19 | −179.9 (3) | C1—C8—C13—C12 | 179.5 (3) |
C19—C5—C6—N2 | −2.9 (5) | C11—C12—C13—C8 | 0.2 (6) |
S1—C5—C6—N2 | 176.9 (3) | C16A—O3A—C15—O2A | −3 (4) |
C19—C5—C6—C7 | 178.6 (3) | C16A—O3A—C15—C2 | −173 (2) |
S1—C5—C6—C7 | −1.6 (3) | C16—O3—C15—O2 | −2 (4) |
N3—C4—C7—C1 | 0.4 (4) | C16—O3—C15—C2 | 164 (2) |
S1—C4—C7—C1 | 179.3 (2) | C1—C2—C15—O2 | 73.6 (15) |
N3—C4—C7—C6 | 178.9 (3) | C3—C2—C15—O2 | −103.2 (15) |
S1—C4—C7—C6 | −2.2 (3) | C1—C2—C15—O2A | 96.1 (12) |
C2—C1—C7—C4 | 0.4 (4) | C3—C2—C15—O2A | −80.6 (12) |
C8—C1—C7—C4 | −177.6 (3) | C1—C2—C15—O3A | −94.9 (19) |
C2—C1—C7—C6 | −177.7 (3) | C3—C2—C15—O3A | 88.4 (19) |
C8—C1—C7—C6 | 4.2 (5) | C1—C2—C15—O3 | −93 (2) |
N2—C6—C7—C4 | −176.0 (3) | C3—C2—C15—O3 | 91 (2) |
C5—C6—C7—C4 | 2.4 (4) | C15—O3—C16—C17 | −170 (3) |
N2—C6—C7—C1 | 2.2 (5) | C15—O3A—C16A—C17A | 175 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N1i | 0.91 | 2.17 | 3.030 (4) | 159 |
C10—H10···O1ii | 0.94 | 2.46 | 3.366 (4) | 162 |
C16A—H16D···O1iii | 0.98 | 2.63 | 3.486 (14) | 146 |
C17A—H17E···N1iv | 0.97 | 2.56 | 3.47 (2) | 156 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+2. |
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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