organic compounds
5-Fluoro-1-[(1-{[(1S,2R,6R,8S,9R)-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
In the title molecule, C23H25FN4O7, the dihedral angle between the indole skeleton (r.m.s. deviation = 0.022 Å) and the triazole moiety is 74.67 (7)°. The molecules pack in a three-dimensional network in the crystal, being linked by C—H⋯O and N—H⋯O hydrogen bonds.
Keywords: crystal structure; triazole; isatin; hydrogen bond.
CCDC reference: 1551162
Structure description
Isatin and its derivatives have received attention in recent years due to their wide variety of biological activities, making them relevant to application as insecticides and fungicides and in a broad range of drug therapies, including as anticancer agents, antibiotics and anti-VIH activities (Malhotra et al., 2011; Ramachandran, 2011; Pandeya et al., 1999). In our work, we are interested in developing new isatin derivatives containing a 1,2,3-triazole nucleus by 1,3-dipolar cycloaddition reactions. As part of this study, we now describe the synthesis and structure of the title compound (Fig. 1).
The r.m.s. deviation of the indole skeleton from planarity is 0.022 Å and the dihedral angle between the mean plane and that of the triazole moiety is 74.67 (7)°. A puckering analysis of the tricyclododecane skeleton gave parameters Q2 = 0.244 (2) Å and φ2 = 266.5 (5)° for the C14/C15/C21/O4/O5 ring, Q2 = 0.305 (2) Å and φ2 = 172.7 (4)° for the C16–C18/O6/O7 ring, and Q = 0.647 (2) Å, θ = 99.1 (2)° and φ = 208.0 (2)° for the C13–C17/O3 ring.
In the crystal (Fig. 2), molecules are linked by weak C—H⋯O and C—H⋯N interactions (Table 1).
Synthesis and crystallization
To a solution of 5-fluoro-1-(prop-2-yn-1-yl)indoline-2,3-dione (0.2 g, 0.98 mmol) in ethanol (15 ml) was added (3aR,5S,5aR,8aS,8bR)-5-azido-2,2,7,7-tetramethyltetrahydro-3aH-di[1,3]dioxolo[4,5-b:4′,5′-d]pyran (0.42 g, 1.47 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 blocks in 62% yield.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1551162
https://doi.org/10.1107/S2414314617007398/hb4145sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617007398/hb4145Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617007398/hb4145Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617007398/hb4145Isup4.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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H25FN4O7 | F(000) = 512 |
Mr = 488.47 | Dx = 1.405 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 11.1688 (2) Å | Cell parameters from 7739 reflections |
b = 9.0576 (2) Å | θ = 3.9–72.4° |
c = 11.9237 (2) Å | µ = 0.94 mm−1 |
β = 106.770 (1)° | T = 150 K |
V = 1154.93 (4) Å3 | Block, yellow |
Z = 2 | 0.22 × 0.14 × 0.12 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4238 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 4039 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.024 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.4°, θmin = 3.9° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −10→10 |
Tmin = 0.85, Tmax = 0.90 | l = −14→14 |
8944 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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.124P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4238 reflections | Δρmax = 0.16 e Å−3 |
320 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 1689 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.16 (7) |
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 - 0.98 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 | ||
F1 | −0.04911 (18) | 0.4129 (2) | 0.95449 (14) | 0.0612 (5) | |
O1 | −0.20772 (16) | 0.2171 (2) | 0.49881 (15) | 0.0453 (4) | |
O2 | −0.0128 (2) | 0.0471 (2) | 0.43373 (18) | 0.0567 (5) | |
O3 | 0.52752 (13) | 0.55460 (16) | 0.80812 (11) | 0.0251 (3) | |
O4 | 0.62417 (15) | 0.7676 (2) | 0.65424 (13) | 0.0366 (4) | |
O5 | 0.68733 (13) | 0.83262 (18) | 0.84705 (12) | 0.0284 (3) | |
O6 | 0.37527 (13) | 0.82992 (17) | 0.87562 (13) | 0.0285 (3) | |
O7 | 0.38313 (14) | 0.58384 (17) | 0.91212 (14) | 0.0318 (3) | |
N1 | 0.10525 (19) | 0.1240 (2) | 0.61668 (17) | 0.0342 (4) | |
N2 | 0.44173 (19) | 0.1415 (2) | 0.63368 (17) | 0.0328 (4) | |
N3 | 0.50589 (18) | 0.2619 (2) | 0.62900 (16) | 0.0308 (4) | |
N4 | 0.42566 (16) | 0.3758 (2) | 0.61216 (15) | 0.0256 (4) | |
C1 | −0.0085 (3) | 0.3410 (3) | 0.8720 (2) | 0.0439 (6) | |
C2 | −0.0915 (2) | 0.3165 (3) | 0.7638 (2) | 0.0381 (5) | |
H2 | −0.1764 | 0.3469 | 0.7454 | 0.046* | |
C3 | −0.0444 (2) | 0.2450 (2) | 0.68326 (19) | 0.0314 (5) | |
C4 | 0.0803 (2) | 0.1984 (3) | 0.71184 (19) | 0.0327 (5) | |
C5 | 0.1617 (2) | 0.2254 (3) | 0.8207 (2) | 0.0440 (6) | |
H5 | 0.2466 | 0.1949 | 0.8400 | 0.053* | |
C6 | 0.1150 (3) | 0.2991 (4) | 0.9015 (2) | 0.0507 (7) | |
H6 | 0.1687 | 0.3206 | 0.9774 | 0.061* | |
C7 | −0.1034 (2) | 0.1984 (3) | 0.5624 (2) | 0.0354 (5) | |
C8 | 0.0000 (2) | 0.1122 (3) | 0.5249 (2) | 0.0374 (5) | |
C9 | 0.2257 (2) | 0.0618 (3) | 0.6191 (2) | 0.0393 (5) | |
H9A | 0.2157 | −0.0017 | 0.5494 | 0.047* | |
H9B | 0.2562 | −0.0008 | 0.6896 | 0.047* | |
C10 | 0.3211 (2) | 0.1795 (2) | 0.62036 (18) | 0.0295 (5) | |
C11 | 0.3094 (2) | 0.3294 (2) | 0.60663 (18) | 0.0280 (4) | |
H11 | 0.2361 | 0.3875 | 0.5957 | 0.034* | |
C12 | 0.4715 (2) | 0.5241 (2) | 0.60179 (18) | 0.0268 (4) | |
H12A | 0.4234 | 0.5671 | 0.5258 | 0.032* | |
H12B | 0.5604 | 0.5187 | 0.6028 | 0.032* | |
C13 | 0.45991 (19) | 0.6235 (2) | 0.70029 (17) | 0.0237 (4) | |
H13 | 0.3698 | 0.6325 | 0.6973 | 0.028* | |
C14 | 0.51263 (19) | 0.7761 (2) | 0.69012 (17) | 0.0254 (4) | |
H14 | 0.4486 | 0.8372 | 0.6330 | 0.030* | |
C15 | 0.55554 (19) | 0.8558 (2) | 0.80891 (18) | 0.0244 (4) | |
H15 | 0.5362 | 0.9636 | 0.7989 | 0.029* | |
C16 | 0.50427 (19) | 0.7914 (2) | 0.90313 (17) | 0.0247 (4) | |
H16 | 0.5510 | 0.8316 | 0.9816 | 0.030* | |
C17 | 0.5044 (2) | 0.6209 (2) | 0.90607 (17) | 0.0259 (4) | |
H17 | 0.5680 | 0.5860 | 0.9788 | 0.031* | |
C18 | 0.3164 (2) | 0.7158 (3) | 0.92364 (19) | 0.0303 (5) | |
C19 | 0.1825 (2) | 0.7038 (3) | 0.8498 (2) | 0.0454 (6) | |
H19A | 0.1800 | 0.6834 | 0.7684 | 0.068* | |
H19B | 0.1391 | 0.7968 | 0.8535 | 0.068* | |
H19C | 0.1414 | 0.6233 | 0.8794 | 0.068* | |
C20 | 0.3298 (3) | 0.7443 (3) | 1.0523 (2) | 0.0410 (6) | |
H20A | 0.2941 | 0.6614 | 1.0846 | 0.061* | |
H20B | 0.2855 | 0.8354 | 1.0601 | 0.061* | |
H20C | 0.4186 | 0.7546 | 1.0952 | 0.061* | |
C21 | 0.7299 (2) | 0.8122 (3) | 0.74624 (18) | 0.0293 (4) | |
C22 | 0.8243 (3) | 0.6889 (4) | 0.7723 (3) | 0.0576 (8) | |
H22A | 0.7871 | 0.6008 | 0.7962 | 0.086* | |
H22B | 0.8978 | 0.7190 | 0.8357 | 0.086* | |
H22C | 0.8496 | 0.6667 | 0.7019 | 0.086* | |
C23 | 0.7782 (3) | 0.9559 (3) | 0.7127 (2) | 0.0521 (7) | |
H23A | 0.8053 | 0.9413 | 0.6423 | 0.078* | |
H23B | 0.8493 | 0.9897 | 0.7771 | 0.078* | |
H23C | 0.7116 | 1.0301 | 0.6970 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0725 (12) | 0.0748 (12) | 0.0426 (9) | −0.0128 (10) | 0.0268 (8) | −0.0144 (8) |
O1 | 0.0361 (10) | 0.0514 (11) | 0.0391 (9) | −0.0054 (8) | −0.0041 (8) | 0.0050 (8) |
O2 | 0.0608 (13) | 0.0598 (13) | 0.0431 (11) | −0.0057 (10) | 0.0046 (9) | −0.0193 (10) |
O3 | 0.0290 (8) | 0.0241 (7) | 0.0210 (7) | 0.0040 (6) | 0.0053 (6) | 0.0022 (5) |
O4 | 0.0339 (9) | 0.0505 (9) | 0.0282 (8) | −0.0157 (7) | 0.0135 (7) | −0.0091 (7) |
O5 | 0.0225 (7) | 0.0365 (8) | 0.0251 (7) | −0.0017 (6) | 0.0051 (5) | −0.0014 (6) |
O6 | 0.0260 (7) | 0.0271 (7) | 0.0334 (8) | 0.0013 (6) | 0.0103 (6) | 0.0016 (6) |
O7 | 0.0352 (8) | 0.0272 (8) | 0.0373 (8) | −0.0035 (6) | 0.0170 (7) | −0.0001 (6) |
N1 | 0.0331 (10) | 0.0325 (10) | 0.0337 (10) | −0.0068 (8) | 0.0045 (8) | −0.0002 (8) |
N2 | 0.0359 (11) | 0.0280 (10) | 0.0345 (10) | 0.0043 (8) | 0.0099 (8) | 0.0009 (7) |
N3 | 0.0335 (10) | 0.0292 (9) | 0.0299 (9) | 0.0051 (7) | 0.0092 (7) | −0.0004 (7) |
N4 | 0.0284 (9) | 0.0257 (9) | 0.0223 (8) | 0.0017 (7) | 0.0070 (7) | −0.0024 (7) |
C1 | 0.0537 (16) | 0.0478 (15) | 0.0340 (12) | −0.0140 (12) | 0.0185 (11) | −0.0038 (11) |
C2 | 0.0396 (13) | 0.0344 (11) | 0.0401 (12) | −0.0070 (10) | 0.0113 (10) | 0.0026 (10) |
C3 | 0.0329 (12) | 0.0283 (11) | 0.0291 (11) | −0.0082 (9) | 0.0025 (9) | 0.0029 (9) |
C4 | 0.0328 (12) | 0.0334 (11) | 0.0293 (10) | −0.0080 (9) | 0.0050 (9) | 0.0049 (9) |
C5 | 0.0339 (13) | 0.0637 (18) | 0.0298 (11) | −0.0094 (11) | 0.0020 (10) | 0.0028 (11) |
C6 | 0.0490 (16) | 0.071 (2) | 0.0270 (12) | −0.0193 (14) | 0.0031 (10) | −0.0022 (12) |
C7 | 0.0348 (13) | 0.0327 (11) | 0.0329 (11) | −0.0094 (9) | 0.0005 (10) | 0.0045 (10) |
C8 | 0.0416 (14) | 0.0323 (12) | 0.0341 (12) | −0.0082 (9) | 0.0042 (10) | −0.0004 (10) |
C9 | 0.0401 (13) | 0.0284 (12) | 0.0490 (14) | −0.0012 (10) | 0.0125 (11) | 0.0033 (10) |
C10 | 0.0330 (12) | 0.0275 (11) | 0.0261 (10) | 0.0004 (8) | 0.0057 (9) | −0.0005 (8) |
C11 | 0.0284 (11) | 0.0265 (10) | 0.0287 (10) | 0.0007 (8) | 0.0074 (8) | −0.0002 (9) |
C12 | 0.0288 (11) | 0.0283 (11) | 0.0230 (9) | −0.0028 (8) | 0.0072 (8) | 0.0006 (8) |
C13 | 0.0229 (10) | 0.0255 (10) | 0.0205 (9) | 0.0010 (7) | 0.0029 (7) | 0.0026 (8) |
C14 | 0.0256 (11) | 0.0269 (10) | 0.0221 (9) | −0.0007 (8) | 0.0044 (8) | 0.0030 (8) |
C15 | 0.0229 (10) | 0.0217 (10) | 0.0263 (10) | −0.0016 (7) | 0.0036 (7) | −0.0004 (8) |
C16 | 0.0237 (10) | 0.0262 (11) | 0.0223 (9) | 0.0000 (7) | 0.0039 (8) | −0.0019 (8) |
C17 | 0.0308 (11) | 0.0255 (10) | 0.0209 (9) | 0.0009 (8) | 0.0067 (8) | 0.0024 (8) |
C18 | 0.0306 (12) | 0.0286 (11) | 0.0339 (11) | −0.0027 (8) | 0.0132 (9) | −0.0015 (9) |
C19 | 0.0295 (13) | 0.0516 (15) | 0.0547 (15) | −0.0071 (11) | 0.0116 (11) | −0.0023 (13) |
C20 | 0.0485 (15) | 0.0424 (14) | 0.0384 (12) | −0.0040 (11) | 0.0228 (11) | −0.0029 (10) |
C21 | 0.0272 (11) | 0.0346 (11) | 0.0267 (10) | −0.0047 (9) | 0.0086 (8) | −0.0027 (9) |
C22 | 0.0545 (18) | 0.070 (2) | 0.0521 (16) | 0.0269 (15) | 0.0212 (13) | 0.0013 (15) |
C23 | 0.0678 (19) | 0.0529 (17) | 0.0401 (14) | −0.0308 (14) | 0.0225 (13) | −0.0071 (12) |
F1—C1 | 1.362 (3) | C9—H9A | 0.9900 |
O1—C7 | 1.204 (3) | C9—H9B | 0.9900 |
O2—C8 | 1.209 (3) | C10—C11 | 1.369 (3) |
O3—C17 | 1.402 (2) | C11—H11 | 0.9500 |
O3—C13 | 1.433 (2) | C12—C13 | 1.515 (3) |
O4—C21 | 1.419 (3) | C12—H12A | 0.9900 |
O4—C14 | 1.431 (2) | C12—H12B | 0.9900 |
O5—C15 | 1.425 (3) | C13—C14 | 1.521 (3) |
O5—C21 | 1.427 (2) | C13—H13 | 1.0000 |
O6—C16 | 1.426 (2) | C14—C15 | 1.538 (3) |
O6—C18 | 1.430 (3) | C14—H14 | 1.0000 |
O7—C17 | 1.418 (3) | C15—C16 | 1.517 (3) |
O7—C18 | 1.436 (3) | C15—H15 | 1.0000 |
N1—C8 | 1.360 (3) | C16—C17 | 1.545 (3) |
N1—C4 | 1.415 (3) | C16—H16 | 1.0000 |
N1—C9 | 1.451 (3) | C17—H17 | 1.0000 |
N2—N3 | 1.315 (3) | C18—C19 | 1.504 (3) |
N2—C10 | 1.355 (3) | C18—C20 | 1.521 (3) |
N3—N4 | 1.343 (3) | C19—H19A | 0.9800 |
N4—C11 | 1.348 (3) | C19—H19B | 0.9800 |
N4—C12 | 1.455 (3) | C19—H19C | 0.9800 |
C1—C2 | 1.372 (4) | C20—H20A | 0.9800 |
C1—C6 | 1.375 (4) | C20—H20B | 0.9800 |
C2—C3 | 1.383 (3) | C20—H20C | 0.9800 |
C2—H2 | 0.9500 | C21—C22 | 1.505 (4) |
C3—C4 | 1.400 (3) | C21—C23 | 1.507 (3) |
C3—C7 | 1.463 (3) | C22—H22A | 0.9800 |
C4—C5 | 1.375 (3) | C22—H22B | 0.9800 |
C5—C6 | 1.392 (4) | C22—H22C | 0.9800 |
C5—H5 | 0.9500 | C23—H23A | 0.9800 |
C6—H6 | 0.9500 | C23—H23B | 0.9800 |
C7—C8 | 1.563 (4) | C23—H23C | 0.9800 |
C9—C10 | 1.504 (3) | ||
C17—O3—C13 | 112.66 (15) | O4—C14—C13 | 111.41 (17) |
C21—O4—C14 | 110.83 (15) | O4—C14—C15 | 103.52 (16) |
C15—O5—C21 | 108.35 (15) | C13—C14—C15 | 112.20 (16) |
C16—O6—C18 | 106.35 (15) | O4—C14—H14 | 109.8 |
C17—O7—C18 | 109.75 (15) | C13—C14—H14 | 109.8 |
C8—N1—C4 | 111.0 (2) | C15—C14—H14 | 109.8 |
C8—N1—C9 | 124.6 (2) | O5—C15—C16 | 106.43 (16) |
C4—N1—C9 | 124.41 (19) | O5—C15—C14 | 104.10 (16) |
N3—N2—C10 | 108.69 (18) | C16—C15—C14 | 114.71 (16) |
N2—N3—N4 | 107.15 (17) | O5—C15—H15 | 110.4 |
N3—N4—C11 | 111.06 (18) | C16—C15—H15 | 110.4 |
N3—N4—C12 | 119.04 (18) | C14—C15—H15 | 110.4 |
C11—N4—C12 | 129.89 (18) | O6—C16—C15 | 107.93 (16) |
F1—C1—C2 | 118.7 (3) | O6—C16—C17 | 104.15 (16) |
F1—C1—C6 | 117.8 (2) | C15—C16—C17 | 113.75 (17) |
C2—C1—C6 | 123.5 (2) | O6—C16—H16 | 110.3 |
C1—C2—C3 | 116.1 (2) | C15—C16—H16 | 110.3 |
C1—C2—H2 | 122.0 | C17—C16—H16 | 110.3 |
C3—C2—H2 | 122.0 | O3—C17—O7 | 110.45 (16) |
C2—C3—C4 | 121.6 (2) | O3—C17—C16 | 114.11 (16) |
C2—C3—C7 | 131.8 (2) | O7—C17—C16 | 104.05 (17) |
C4—C3—C7 | 106.7 (2) | O3—C17—H17 | 109.4 |
C5—C4—C3 | 121.1 (2) | O7—C17—H17 | 109.4 |
C5—C4—N1 | 127.7 (2) | C16—C17—H17 | 109.4 |
C3—C4—N1 | 111.15 (18) | O6—C18—O7 | 104.61 (15) |
C4—C5—C6 | 117.4 (3) | O6—C18—C19 | 108.17 (19) |
C4—C5—H5 | 121.3 | O7—C18—C19 | 109.86 (19) |
C6—C5—H5 | 121.3 | O6—C18—C20 | 110.99 (18) |
C1—C6—C5 | 120.3 (2) | O7—C18—C20 | 109.60 (18) |
C1—C6—H6 | 119.9 | C19—C18—C20 | 113.3 (2) |
C5—C6—H6 | 119.9 | C18—C19—H19A | 109.5 |
O1—C7—C3 | 131.2 (2) | C18—C19—H19B | 109.5 |
O1—C7—C8 | 123.4 (2) | H19A—C19—H19B | 109.5 |
C3—C7—C8 | 105.41 (19) | C18—C19—H19C | 109.5 |
O2—C8—N1 | 127.8 (3) | H19A—C19—H19C | 109.5 |
O2—C8—C7 | 126.6 (2) | H19B—C19—H19C | 109.5 |
N1—C8—C7 | 105.63 (19) | C18—C20—H20A | 109.5 |
N1—C9—C10 | 112.0 (2) | C18—C20—H20B | 109.5 |
N1—C9—H9A | 109.2 | H20A—C20—H20B | 109.5 |
C10—C9—H9A | 109.2 | C18—C20—H20C | 109.5 |
N1—C9—H9B | 109.2 | H20A—C20—H20C | 109.5 |
C10—C9—H9B | 109.2 | H20B—C20—H20C | 109.5 |
H9A—C9—H9B | 107.9 | O4—C21—O5 | 106.43 (16) |
N2—C10—C11 | 108.8 (2) | O4—C21—C22 | 109.0 (2) |
N2—C10—C9 | 119.9 (2) | O5—C21—C22 | 107.85 (19) |
C11—C10—C9 | 131.2 (2) | O4—C21—C23 | 108.8 (2) |
N4—C11—C10 | 104.28 (19) | O5—C21—C23 | 110.09 (19) |
N4—C11—H11 | 127.9 | C22—C21—C23 | 114.3 (2) |
C10—C11—H11 | 127.9 | C21—C22—H22A | 109.5 |
N4—C12—C13 | 111.82 (16) | C21—C22—H22B | 109.5 |
N4—C12—H12A | 109.3 | H22A—C22—H22B | 109.5 |
C13—C12—H12A | 109.3 | C21—C22—H22C | 109.5 |
N4—C12—H12B | 109.3 | H22A—C22—H22C | 109.5 |
C13—C12—H12B | 109.3 | H22B—C22—H22C | 109.5 |
H12A—C12—H12B | 107.9 | C21—C23—H23A | 109.5 |
O3—C13—C12 | 107.23 (16) | C21—C23—H23B | 109.5 |
O3—C13—C14 | 110.57 (16) | H23A—C23—H23B | 109.5 |
C12—C13—C14 | 110.90 (16) | C21—C23—H23C | 109.5 |
O3—C13—H13 | 109.4 | H23A—C23—H23C | 109.5 |
C12—C13—H13 | 109.4 | H23B—C23—H23C | 109.5 |
C14—C13—H13 | 109.4 | ||
C10—N2—N3—N4 | −0.3 (2) | C11—N4—C12—C13 | 64.1 (3) |
N2—N3—N4—C11 | 0.4 (2) | C17—O3—C13—C12 | −168.58 (16) |
N2—N3—N4—C12 | −179.12 (17) | C17—O3—C13—C14 | 70.4 (2) |
F1—C1—C2—C3 | 179.1 (2) | N4—C12—C13—O3 | 57.2 (2) |
C6—C1—C2—C3 | 0.3 (4) | N4—C12—C13—C14 | 177.97 (17) |
C1—C2—C3—C4 | 1.1 (3) | C21—O4—C14—C13 | −111.73 (19) |
C1—C2—C3—C7 | 178.9 (2) | C21—O4—C14—C15 | 9.1 (2) |
C2—C3—C4—C5 | −1.6 (4) | O3—C13—C14—O4 | 79.27 (19) |
C7—C3—C4—C5 | −179.9 (2) | C12—C13—C14—O4 | −39.5 (2) |
C2—C3—C4—N1 | 178.1 (2) | O3—C13—C14—C15 | −36.3 (2) |
C7—C3—C4—N1 | −0.2 (2) | C12—C13—C14—C15 | −155.10 (17) |
C8—N1—C4—C5 | 177.1 (2) | C21—O5—C15—C16 | 148.22 (17) |
C9—N1—C4—C5 | 0.0 (4) | C21—O5—C15—C14 | 26.7 (2) |
C8—N1—C4—C3 | −2.6 (3) | O4—C14—C15—O5 | −21.5 (2) |
C9—N1—C4—C3 | −179.7 (2) | C13—C14—C15—O5 | 98.75 (18) |
C3—C4—C5—C6 | 0.7 (4) | O4—C14—C15—C16 | −137.38 (18) |
N1—C4—C5—C6 | −178.9 (2) | C13—C14—C15—C16 | −17.1 (2) |
F1—C1—C6—C5 | −180.0 (3) | C18—O6—C16—C15 | 151.56 (16) |
C2—C1—C6—C5 | −1.1 (4) | C18—O6—C16—C17 | 30.35 (19) |
C4—C5—C6—C1 | 0.6 (4) | O5—C15—C16—O6 | 172.38 (15) |
C2—C3—C7—O1 | 4.5 (4) | C14—C15—C16—O6 | −73.1 (2) |
C4—C3—C7—O1 | −177.5 (2) | O5—C15—C16—C17 | −72.6 (2) |
C2—C3—C7—C8 | −175.5 (2) | C14—C15—C16—C17 | 41.9 (2) |
C4—C3—C7—C8 | 2.5 (2) | C13—O3—C17—O7 | 73.2 (2) |
C4—N1—C8—O2 | −174.8 (3) | C13—O3—C17—C16 | −43.6 (2) |
C9—N1—C8—O2 | 2.2 (4) | C18—O7—C17—O3 | −128.04 (17) |
C4—N1—C8—C7 | 4.0 (2) | C18—O7—C17—C16 | −5.2 (2) |
C9—N1—C8—C7 | −178.9 (2) | O6—C16—C17—O3 | 105.06 (18) |
O1—C7—C8—O2 | −5.2 (4) | C15—C16—C17—O3 | −12.2 (3) |
C3—C7—C8—O2 | 174.8 (2) | O6—C16—C17—O7 | −15.4 (2) |
O1—C7—C8—N1 | 176.0 (2) | C15—C16—C17—O7 | −132.63 (17) |
C3—C7—C8—N1 | −4.1 (2) | C16—O6—C18—O7 | −33.89 (19) |
C8—N1—C9—C10 | 112.8 (2) | C16—O6—C18—C19 | −150.96 (19) |
C4—N1—C9—C10 | −70.5 (3) | C16—O6—C18—C20 | 84.2 (2) |
N3—N2—C10—C11 | 0.1 (2) | C17—O7—C18—O6 | 23.9 (2) |
N3—N2—C10—C9 | 178.42 (19) | C17—O7—C18—C19 | 139.75 (19) |
N1—C9—C10—N2 | 173.84 (19) | C17—O7—C18—C20 | −95.2 (2) |
N1—C9—C10—C11 | −8.3 (4) | C14—O4—C21—O5 | 6.9 (2) |
N3—N4—C11—C10 | −0.3 (2) | C14—O4—C21—C22 | 123.0 (2) |
C12—N4—C11—C10 | 179.12 (19) | C14—O4—C21—C23 | −111.7 (2) |
N2—C10—C11—N4 | 0.1 (2) | C15—O5—C21—O4 | −21.6 (2) |
C9—C10—C11—N4 | −177.9 (2) | C15—O5—C21—C22 | −138.4 (2) |
N3—N4—C12—C13 | −116.6 (2) | C15—O5—C21—C23 | 96.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O5i | 0.95 | 2.24 | 3.184 (3) | 170 |
C15—H15···N2ii | 1.00 | 2.53 | 3.338 (3) | 138 |
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) x, y+1, z. |
Acknowledgements
The support of NSF–MRI Grant #1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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