organic compounds
1-[(1-{[(1S,2R,6R,8R,9S)-4,4,11,11-Tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl}-1H-1,2,3-triazol-4-yl)methyl]-2,3-dihydro-1H-indole-2,3-dione
aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco, bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and cLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco
*Correspondence e-mail: amalhaoudi2017@gmail.com
The title compound,C23H26N4O7, adopts a Z-shaped conformation, with a dihedral angle between the mean planes of the dihydroindole and triazole rings of 70.36 (7)°. In the crystal, C—H⋯O interactions connect the molecules into zigzag chains running along the b-axis direction.
Keywords: crystal structure; isatins; triazole; hydrogen bond.
CCDC reference: 1547809
Structure description
Isatins are very useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest. The wide variety of biological activities shown by isatin and its derivatives are relevant to applications as insecticides and fungicides and in a broad range of drug therapies, including anticancer drugs, antibiotics and antidepressants (Bhrigu et al., 2010; da Silva et al., 2001; Ramachandran, 2011; Smitha et al., 2008). As part of our studies in this area, we have undertaken the synthesis and of the title compound (Fig. 1).
The dihedral angle between the mean planes of the C1–C6 and triazole rings is 70.36 (7)°. A Cremer–Pople puckering analysis of the C13–C17,O3 ring gave parameters Q = 0.6549 (16) Å, θ = 99.92 (15)° and φ = 218.02 (15)°. For the O4,C14,C15,O5,C18 ring, the parameters are Q(2) = 0.2959 (17) Å and φ(2) = 307.9 (3)° while for the O6,C16,C17,O7,C21 ring they are Q(2) = 0.2860 (16) Å and φ(2) = 196.1 (3)°. The conformation of the O4,C16,C15,O5,C18 ring is twisted on O5—C18, that of the O6,C16,C17,O7,C21 ring is twisted on O6—C16 and that of the C13⋯C17,O3 ring is best described as a twist–boat.
In the crystal, C—H⋯O interactions (Table 1) connect the molecules into zigzag chains running along the b-axis direction. The crystal packing is shown in Fig. 2.
Synthesis and crystallization
To a solution of 1-(prop-2-yn-1-yl)idoline-2,3-dione (0.2 g, 1.08 mmol) in ethanol (15 ml) was added (3aR,5S,5aR,8aS,8bR)-5-azido-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran (0.46 g, 1.62 mmol). The mixture was stirred under reflux for 24 h. After completion of the reaction (monitored by TLC), the solution was concentrated and the residue was purified by on silica gel by using a 3:1 (v/v) mixture of hexane and ethyl acetate. Crystals were obtained when the solvent was allowed to evaporate. The solid product was purified by recrystallization from ethanol solution to afford yellow crystals in 62% yield.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1547809
https://doi.org/10.1107/S2414314617006708/bt4048sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006708/bt4048Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006708/bt4048Isup3.tif
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006708/bt4048Isup4.cml
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H26N4O7 | F(000) = 992 |
Mr = 470.48 | Dx = 1.365 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54178 Å |
a = 25.6622 (8) Å | Cell parameters from 9918 reflections |
b = 8.7731 (3) Å | θ = 3.5–72.5° |
c = 10.3928 (3) Å | µ = 0.86 mm−1 |
β = 101.847 (1)° | T = 150 K |
V = 2289.96 (13) Å3 | Thick plate, yellow |
Z = 4 | 0.18 × 0.18 × 0.09 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4250 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 4142 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.028 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.5°, θmin = 3.5° |
ω scans | h = −31→31 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −10→10 |
Tmin = 0.86, Tmax = 0.92 | l = −12→12 |
13935 measured reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.4737P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.025 | (Δ/σ)max = 0.001 |
wR(F2) = 0.064 | Δρmax = 0.15 e Å−3 |
S = 1.02 | Δρmin = −0.12 e Å−3 |
4250 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
312 parameters | Extinction coefficient: 0.00122 (12) |
1 restraint | Absolute structure: Flack x determined using 1738 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Hydrogen site location: inferred from neighbouring sites | Absolute structure parameter: 0.06 (5) |
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. H-atoms were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. H atoms were placed in calculated positions (C—H = 0.95–1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.38504 (6) | 0.73451 (17) | −0.11559 (13) | 0.0422 (3) | |
O2 | 0.42118 (5) | 0.46504 (16) | 0.04958 (13) | 0.0361 (3) | |
O3 | 0.63848 (4) | 0.14283 (14) | 0.27385 (11) | 0.0256 (3) | |
O4 | 0.73597 (5) | 0.17670 (15) | 0.17487 (12) | 0.0318 (3) | |
O5 | 0.73377 (5) | −0.07332 (15) | 0.22667 (12) | 0.0306 (3) | |
O6 | 0.70228 (4) | 0.00891 (15) | 0.54268 (10) | 0.0273 (3) | |
O7 | 0.61358 (4) | 0.03958 (17) | 0.45789 (11) | 0.0308 (3) | |
N1 | 0.46396 (6) | 0.65011 (18) | 0.19074 (14) | 0.0285 (3) | |
N2 | 0.57957 (6) | 0.5944 (2) | 0.41853 (16) | 0.0361 (4) | |
N3 | 0.62799 (6) | 0.5552 (2) | 0.40657 (15) | 0.0351 (4) | |
N4 | 0.62257 (5) | 0.46388 (16) | 0.30101 (14) | 0.0263 (3) | |
C1 | 0.46996 (6) | 0.8105 (2) | 0.18610 (17) | 0.0275 (4) | |
C2 | 0.50002 (7) | 0.9035 (2) | 0.28016 (18) | 0.0327 (4) | |
H2 | 0.5212 | 0.8633 | 0.3586 | 0.039* | |
C3 | 0.49773 (7) | 1.0598 (2) | 0.2540 (2) | 0.0364 (4) | |
H3 | 0.5180 | 1.1270 | 0.3165 | 0.044* | |
C4 | 0.46679 (8) | 1.1205 (2) | 0.1399 (2) | 0.0378 (4) | |
H4 | 0.4657 | 1.2277 | 0.1267 | 0.045* | |
C5 | 0.43747 (7) | 1.0249 (2) | 0.04507 (18) | 0.0333 (4) | |
H5 | 0.4165 | 1.0651 | −0.0336 | 0.040* | |
C6 | 0.43983 (6) | 0.8696 (2) | 0.06881 (17) | 0.0284 (4) | |
C7 | 0.41433 (7) | 0.7402 (2) | −0.00880 (17) | 0.0306 (4) | |
C8 | 0.43274 (7) | 0.5968 (2) | 0.07729 (17) | 0.0289 (4) | |
C9 | 0.48516 (7) | 0.5535 (2) | 0.30425 (17) | 0.0308 (4) | |
H9A | 0.4664 | 0.4543 | 0.2936 | 0.037* | |
H9B | 0.4780 | 0.6025 | 0.3847 | 0.037* | |
C10 | 0.54375 (6) | 0.5266 (2) | 0.32078 (15) | 0.0277 (3) | |
C11 | 0.57112 (7) | 0.4422 (2) | 0.24590 (17) | 0.0276 (3) | |
H11 | 0.5568 | 0.3816 | 0.1713 | 0.033* | |
C12 | 0.66918 (6) | 0.3967 (2) | 0.26235 (17) | 0.0283 (3) | |
H12A | 0.7002 | 0.4651 | 0.2885 | 0.034* | |
H12B | 0.6623 | 0.3842 | 0.1657 | 0.034* | |
C13 | 0.68127 (6) | 0.2430 (2) | 0.32814 (15) | 0.0242 (3) | |
H13 | 0.6823 | 0.2549 | 0.4243 | 0.029* | |
C14 | 0.73352 (6) | 0.1746 (2) | 0.31067 (15) | 0.0252 (3) | |
H14 | 0.7641 | 0.2326 | 0.3635 | 0.030* | |
C15 | 0.73768 (6) | 0.0043 (2) | 0.34853 (15) | 0.0259 (3) | |
H15 | 0.7729 | −0.0171 | 0.4074 | 0.031* | |
C16 | 0.69277 (6) | −0.0520 (2) | 0.41186 (15) | 0.0253 (3) | |
H16 | 0.6923 | −0.1660 | 0.4143 | 0.030* | |
C17 | 0.63744 (6) | 0.0097 (2) | 0.34884 (15) | 0.0251 (3) | |
H17 | 0.6167 | −0.0712 | 0.2926 | 0.030* | |
C18 | 0.75196 (7) | 0.0290 (2) | 0.13954 (17) | 0.0307 (4) | |
C19 | 0.81202 (8) | 0.0232 (3) | 0.1570 (2) | 0.0419 (4) | |
H19A | 0.8284 | 0.0425 | 0.2493 | 0.063* | |
H19B | 0.8237 | 0.1011 | 0.1015 | 0.063* | |
H19C | 0.8228 | −0.0777 | 0.1314 | 0.063* | |
C20 | 0.72339 (10) | −0.0058 (3) | 0.00086 (19) | 0.0489 (5) | |
H20A | 0.7321 | −0.1096 | −0.0224 | 0.073* | |
H20B | 0.7346 | 0.0668 | −0.0597 | 0.073* | |
H20C | 0.6849 | 0.0027 | −0.0054 | 0.073* | |
C21 | 0.65171 (6) | 0.0218 (2) | 0.57957 (15) | 0.0286 (4) | |
C22 | 0.65193 (8) | 0.1628 (3) | 0.66276 (19) | 0.0388 (4) | |
H22A | 0.6820 | 0.1581 | 0.7381 | 0.058* | |
H22B | 0.6185 | 0.1685 | 0.6943 | 0.058* | |
H22C | 0.6554 | 0.2533 | 0.6100 | 0.058* | |
C23 | 0.63892 (7) | −0.1216 (2) | 0.64715 (18) | 0.0353 (4) | |
H23A | 0.6392 | −0.2090 | 0.5885 | 0.053* | |
H23B | 0.6036 | −0.1119 | 0.6687 | 0.053* | |
H23C | 0.6657 | −0.1370 | 0.7281 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0486 (8) | 0.0401 (8) | 0.0323 (7) | 0.0053 (6) | −0.0050 (6) | −0.0013 (6) |
O2 | 0.0386 (7) | 0.0316 (7) | 0.0380 (7) | 0.0035 (5) | 0.0075 (5) | −0.0013 (5) |
O3 | 0.0200 (5) | 0.0306 (7) | 0.0244 (5) | −0.0002 (4) | 0.0002 (4) | 0.0016 (5) |
O4 | 0.0384 (7) | 0.0323 (7) | 0.0284 (6) | 0.0081 (5) | 0.0150 (5) | 0.0038 (5) |
O5 | 0.0343 (6) | 0.0291 (6) | 0.0313 (6) | 0.0004 (5) | 0.0140 (5) | −0.0033 (5) |
O6 | 0.0210 (5) | 0.0396 (7) | 0.0210 (5) | 0.0008 (5) | 0.0035 (4) | 0.0016 (5) |
O7 | 0.0204 (5) | 0.0467 (8) | 0.0254 (5) | 0.0041 (5) | 0.0051 (4) | 0.0023 (5) |
N1 | 0.0249 (7) | 0.0316 (8) | 0.0286 (7) | 0.0045 (6) | 0.0044 (5) | 0.0036 (6) |
N2 | 0.0306 (7) | 0.0428 (10) | 0.0335 (8) | 0.0077 (7) | 0.0035 (6) | −0.0068 (7) |
N3 | 0.0297 (7) | 0.0396 (9) | 0.0344 (8) | 0.0064 (6) | 0.0029 (6) | −0.0080 (7) |
N4 | 0.0264 (7) | 0.0260 (7) | 0.0265 (6) | 0.0035 (5) | 0.0056 (5) | 0.0003 (6) |
C1 | 0.0208 (7) | 0.0318 (9) | 0.0313 (9) | 0.0033 (6) | 0.0089 (6) | 0.0013 (7) |
C2 | 0.0234 (7) | 0.0403 (10) | 0.0335 (8) | 0.0035 (7) | 0.0038 (7) | 0.0000 (8) |
C3 | 0.0258 (8) | 0.0386 (11) | 0.0432 (10) | −0.0026 (7) | 0.0036 (7) | −0.0058 (8) |
C4 | 0.0330 (9) | 0.0310 (10) | 0.0490 (11) | 0.0013 (7) | 0.0076 (8) | 0.0007 (8) |
C5 | 0.0301 (8) | 0.0340 (10) | 0.0355 (9) | 0.0051 (7) | 0.0062 (7) | 0.0037 (8) |
C6 | 0.0231 (7) | 0.0326 (9) | 0.0300 (8) | 0.0039 (7) | 0.0065 (6) | 0.0019 (7) |
C7 | 0.0291 (8) | 0.0338 (9) | 0.0297 (8) | 0.0051 (7) | 0.0077 (7) | 0.0011 (7) |
C8 | 0.0253 (7) | 0.0324 (10) | 0.0298 (8) | 0.0039 (7) | 0.0077 (6) | −0.0003 (7) |
C9 | 0.0263 (8) | 0.0383 (10) | 0.0283 (8) | 0.0055 (7) | 0.0069 (6) | 0.0075 (7) |
C10 | 0.0274 (8) | 0.0304 (9) | 0.0249 (7) | 0.0049 (7) | 0.0042 (6) | 0.0033 (7) |
C11 | 0.0267 (7) | 0.0289 (9) | 0.0265 (7) | 0.0013 (6) | 0.0038 (6) | 0.0004 (6) |
C12 | 0.0254 (7) | 0.0297 (9) | 0.0312 (8) | 0.0034 (7) | 0.0094 (6) | 0.0019 (7) |
C13 | 0.0209 (7) | 0.0275 (8) | 0.0236 (7) | −0.0003 (6) | 0.0036 (6) | −0.0010 (6) |
C14 | 0.0216 (7) | 0.0310 (9) | 0.0235 (7) | 0.0003 (6) | 0.0055 (6) | 0.0000 (6) |
C15 | 0.0229 (7) | 0.0310 (9) | 0.0244 (7) | 0.0026 (6) | 0.0060 (6) | 0.0012 (7) |
C16 | 0.0228 (7) | 0.0300 (9) | 0.0232 (7) | 0.0008 (6) | 0.0049 (6) | 0.0004 (6) |
C17 | 0.0213 (7) | 0.0298 (8) | 0.0241 (7) | −0.0016 (6) | 0.0043 (6) | −0.0008 (7) |
C18 | 0.0342 (8) | 0.0318 (9) | 0.0294 (8) | 0.0047 (7) | 0.0141 (7) | 0.0002 (7) |
C19 | 0.0354 (9) | 0.0421 (11) | 0.0542 (11) | 0.0077 (8) | 0.0235 (8) | 0.0085 (10) |
C20 | 0.0599 (13) | 0.0568 (14) | 0.0307 (9) | 0.0035 (11) | 0.0108 (9) | −0.0072 (10) |
C21 | 0.0222 (7) | 0.0407 (10) | 0.0233 (7) | 0.0019 (7) | 0.0053 (6) | 0.0025 (7) |
C22 | 0.0428 (10) | 0.0442 (11) | 0.0311 (9) | 0.0017 (9) | 0.0115 (8) | −0.0043 (8) |
C23 | 0.0305 (8) | 0.0449 (11) | 0.0324 (9) | 0.0003 (8) | 0.0112 (7) | 0.0059 (8) |
O1—C7 | 1.207 (2) | C9—H9A | 0.9900 |
O2—C8 | 1.213 (2) | C9—H9B | 0.9900 |
O3—C17 | 1.408 (2) | C10—C11 | 1.368 (2) |
O3—C13 | 1.4290 (19) | C11—H11 | 0.9500 |
O4—C14 | 1.4256 (19) | C12—C13 | 1.515 (2) |
O4—C18 | 1.430 (2) | C12—H12A | 0.9900 |
O5—C18 | 1.420 (2) | C12—H12B | 0.9900 |
O5—C15 | 1.423 (2) | C13—C14 | 1.514 (2) |
O6—C21 | 1.4313 (18) | C13—H13 | 1.0000 |
O6—C16 | 1.4344 (19) | C14—C15 | 1.543 (2) |
O7—C17 | 1.4189 (19) | C14—H14 | 1.0000 |
O7—C21 | 1.4396 (19) | C15—C16 | 1.522 (2) |
N1—C8 | 1.365 (2) | C15—H15 | 1.0000 |
N1—C1 | 1.418 (2) | C16—C17 | 1.535 (2) |
N1—C9 | 1.464 (2) | C16—H16 | 1.0000 |
N2—N3 | 1.319 (2) | C17—H17 | 1.0000 |
N2—C10 | 1.359 (2) | C18—C20 | 1.508 (3) |
N3—N4 | 1.343 (2) | C18—C19 | 1.515 (2) |
N4—C11 | 1.341 (2) | C19—H19A | 0.9800 |
N4—C12 | 1.462 (2) | C19—H19B | 0.9800 |
C1—C2 | 1.381 (3) | C19—H19C | 0.9800 |
C1—C6 | 1.402 (2) | C20—H20A | 0.9800 |
C2—C3 | 1.396 (3) | C20—H20B | 0.9800 |
C2—H2 | 0.9500 | C20—H20C | 0.9800 |
C3—C4 | 1.391 (3) | C21—C22 | 1.508 (3) |
C3—H3 | 0.9500 | C21—C23 | 1.510 (3) |
C4—C5 | 1.392 (3) | C22—H22A | 0.9800 |
C4—H4 | 0.9500 | C22—H22B | 0.9800 |
C5—C6 | 1.384 (3) | C22—H22C | 0.9800 |
C5—H5 | 0.9500 | C23—H23A | 0.9800 |
C6—C7 | 1.467 (3) | C23—H23B | 0.9800 |
C7—C8 | 1.560 (3) | C23—H23C | 0.9800 |
C9—C10 | 1.497 (2) | ||
C17—O3—C13 | 113.08 (12) | O4—C14—C13 | 109.50 (13) |
C14—O4—C18 | 108.40 (13) | O4—C14—C15 | 104.49 (13) |
C18—O5—C15 | 107.02 (13) | C13—C14—C15 | 111.71 (13) |
C21—O6—C16 | 107.23 (11) | O4—C14—H14 | 110.3 |
C17—O7—C21 | 110.78 (11) | C13—C14—H14 | 110.3 |
C8—N1—C1 | 111.06 (14) | C15—C14—H14 | 110.3 |
C8—N1—C9 | 123.58 (16) | O5—C15—C16 | 107.94 (13) |
C1—N1—C9 | 125.25 (15) | O5—C15—C14 | 104.35 (12) |
N3—N2—C10 | 108.73 (15) | C16—C15—C14 | 113.93 (13) |
N2—N3—N4 | 106.91 (14) | O5—C15—H15 | 110.1 |
C11—N4—N3 | 111.19 (14) | C16—C15—H15 | 110.1 |
C11—N4—C12 | 127.95 (15) | C14—C15—H15 | 110.1 |
N3—N4—C12 | 120.80 (14) | O6—C16—C15 | 107.00 (13) |
C2—C1—C6 | 121.68 (17) | O6—C16—C17 | 103.62 (12) |
C2—C1—N1 | 127.68 (17) | C15—C16—C17 | 114.66 (14) |
C6—C1—N1 | 110.63 (16) | O6—C16—H16 | 110.4 |
C1—C2—C3 | 116.58 (17) | C15—C16—H16 | 110.4 |
C1—C2—H2 | 121.7 | C17—C16—H16 | 110.4 |
C3—C2—H2 | 121.7 | O3—C17—O7 | 110.42 (14) |
C4—C3—C2 | 122.39 (18) | O3—C17—C16 | 114.07 (13) |
C4—C3—H3 | 118.8 | O7—C17—C16 | 103.74 (12) |
C2—C3—H3 | 118.8 | O3—C17—H17 | 109.5 |
C3—C4—C5 | 120.29 (19) | O7—C17—H17 | 109.5 |
C3—C4—H4 | 119.9 | C16—C17—H17 | 109.5 |
C5—C4—H4 | 119.9 | O5—C18—O4 | 105.05 (12) |
C6—C5—C4 | 118.00 (17) | O5—C18—C20 | 108.82 (16) |
C6—C5—H5 | 121.0 | O4—C18—C20 | 108.66 (16) |
C4—C5—H5 | 121.0 | O5—C18—C19 | 111.23 (15) |
C5—C6—C1 | 121.01 (17) | O4—C18—C19 | 109.75 (16) |
C5—C6—C7 | 131.76 (17) | C20—C18—C19 | 112.99 (16) |
C1—C6—C7 | 107.22 (16) | C18—C19—H19A | 109.5 |
O1—C7—C6 | 131.38 (18) | C18—C19—H19B | 109.5 |
O1—C7—C8 | 123.52 (18) | H19A—C19—H19B | 109.5 |
C6—C7—C8 | 105.10 (14) | C18—C19—H19C | 109.5 |
O2—C8—N1 | 127.09 (17) | H19A—C19—H19C | 109.5 |
O2—C8—C7 | 126.99 (16) | H19B—C19—H19C | 109.5 |
N1—C8—C7 | 105.92 (15) | C18—C20—H20A | 109.5 |
N1—C9—C10 | 112.49 (14) | C18—C20—H20B | 109.5 |
N1—C9—H9A | 109.1 | H20A—C20—H20B | 109.5 |
C10—C9—H9A | 109.1 | C18—C20—H20C | 109.5 |
N1—C9—H9B | 109.1 | H20A—C20—H20C | 109.5 |
C10—C9—H9B | 109.1 | H20B—C20—H20C | 109.5 |
H9A—C9—H9B | 107.8 | O6—C21—O7 | 105.27 (11) |
N2—C10—C11 | 108.34 (15) | O6—C21—C22 | 108.76 (15) |
N2—C10—C9 | 121.73 (16) | O7—C21—C22 | 109.68 (16) |
C11—C10—C9 | 129.88 (16) | O6—C21—C23 | 110.75 (15) |
N4—C11—C10 | 104.82 (15) | O7—C21—C23 | 108.99 (14) |
N4—C11—H11 | 127.6 | C22—C21—C23 | 113.10 (14) |
C10—C11—H11 | 127.6 | C21—C22—H22A | 109.5 |
N4—C12—C13 | 109.77 (13) | C21—C22—H22B | 109.5 |
N4—C12—H12A | 109.7 | H22A—C22—H22B | 109.5 |
C13—C12—H12A | 109.7 | C21—C22—H22C | 109.5 |
N4—C12—H12B | 109.7 | H22A—C22—H22C | 109.5 |
C13—C12—H12B | 109.7 | H22B—C22—H22C | 109.5 |
H12A—C12—H12B | 108.2 | C21—C23—H23A | 109.5 |
O3—C13—C14 | 109.68 (14) | C21—C23—H23B | 109.5 |
O3—C13—C12 | 107.43 (13) | H23A—C23—H23B | 109.5 |
C14—C13—C12 | 113.77 (13) | C21—C23—H23C | 109.5 |
O3—C13—H13 | 108.6 | H23A—C23—H23C | 109.5 |
C14—C13—H13 | 108.6 | H23B—C23—H23C | 109.5 |
C12—C13—H13 | 108.6 | ||
C10—N2—N3—N4 | 0.4 (2) | C17—O3—C13—C14 | 71.36 (16) |
N2—N3—N4—C11 | −0.8 (2) | C17—O3—C13—C12 | −164.51 (12) |
N2—N3—N4—C12 | −178.34 (16) | N4—C12—C13—O3 | 67.01 (16) |
C8—N1—C1—C2 | −177.55 (17) | N4—C12—C13—C14 | −171.38 (14) |
C9—N1—C1—C2 | 6.2 (3) | C18—O4—C14—C13 | −131.51 (15) |
C8—N1—C1—C6 | 3.03 (19) | C18—O4—C14—C15 | −11.73 (16) |
C9—N1—C1—C6 | −173.24 (15) | O3—C13—C14—O4 | 69.64 (17) |
C6—C1—C2—C3 | 1.7 (3) | C12—C13—C14—O4 | −50.70 (19) |
N1—C1—C2—C3 | −177.68 (17) | O3—C13—C14—C15 | −45.62 (17) |
C1—C2—C3—C4 | 0.3 (3) | C12—C13—C14—C15 | −165.96 (13) |
C2—C3—C4—C5 | −1.4 (3) | C18—O5—C15—C16 | 147.57 (14) |
C3—C4—C5—C6 | 0.6 (3) | C18—O5—C15—C14 | 26.05 (16) |
C4—C5—C6—C1 | 1.3 (3) | O4—C14—C15—O5 | −8.66 (16) |
C4—C5—C6—C7 | 179.91 (18) | C13—C14—C15—O5 | 109.63 (14) |
C2—C1—C6—C5 | −2.5 (3) | O4—C14—C15—C16 | −126.14 (13) |
N1—C1—C6—C5 | 176.93 (16) | C13—C14—C15—C16 | −7.85 (18) |
C2—C1—C6—C7 | 178.58 (15) | C21—O6—C16—C15 | 152.78 (14) |
N1—C1—C6—C7 | −1.97 (19) | C21—O6—C16—C17 | 31.24 (16) |
C5—C6—C7—O1 | 1.4 (3) | O5—C15—C16—O6 | 171.12 (12) |
C1—C6—C7—O1 | −179.84 (19) | C14—C15—C16—O6 | −73.50 (16) |
C5—C6—C7—C8 | −178.37 (18) | O5—C15—C16—C17 | −74.59 (18) |
C1—C6—C7—C8 | 0.35 (18) | C14—C15—C16—C17 | 40.79 (19) |
C1—N1—C8—O2 | 178.09 (17) | C13—O3—C17—O7 | 80.43 (15) |
C9—N1—C8—O2 | −5.6 (3) | C13—O3—C17—C16 | −35.92 (18) |
C1—N1—C8—C7 | −2.64 (17) | C21—O7—C17—O3 | −114.66 (15) |
C9—N1—C8—C7 | 173.71 (14) | C21—O7—C17—C16 | 7.95 (19) |
O1—C7—C8—O2 | 0.8 (3) | O6—C16—C17—O3 | 96.50 (15) |
C6—C7—C8—O2 | −179.34 (17) | C15—C16—C17—O3 | −19.7 (2) |
O1—C7—C8—N1 | −178.44 (17) | O6—C16—C17—O7 | −23.67 (16) |
C6—C7—C8—N1 | 1.39 (17) | C15—C16—C17—O7 | −139.92 (14) |
C8—N1—C9—C10 | 107.47 (19) | C15—O5—C18—O4 | −33.89 (16) |
C1—N1—C9—C10 | −76.7 (2) | C15—O5—C18—C20 | −150.09 (15) |
N3—N2—C10—C11 | 0.1 (2) | C15—O5—C18—C19 | 84.80 (17) |
N3—N2—C10—C9 | −177.57 (17) | C14—O4—C18—O5 | 28.08 (17) |
N1—C9—C10—N2 | 107.04 (19) | C14—O4—C18—C20 | 144.40 (16) |
N1—C9—C10—C11 | −70.1 (3) | C14—O4—C18—C19 | −91.59 (16) |
N3—N4—C11—C10 | 0.9 (2) | C16—O6—C21—O7 | −26.73 (18) |
C12—N4—C11—C10 | 178.17 (16) | C16—O6—C21—C22 | −144.20 (14) |
N2—C10—C11—N4 | −0.6 (2) | C16—O6—C21—C23 | 90.93 (16) |
C9—C10—C11—N4 | 176.84 (18) | C17—O7—C21—O6 | 10.9 (2) |
C11—N4—C12—C13 | −86.2 (2) | C17—O7—C21—C22 | 127.73 (15) |
N3—N4—C12—C13 | 90.85 (19) | C17—O7—C21—C23 | −107.96 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O1i | 1.00 | 2.50 | 3.386 (2) | 147 |
Symmetry code: (i) −x+1, y−1, −z. |
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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