organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

CROSSMARK_Color_square_no_text.svg

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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 3 May 2017; accepted 4 May 2017; online 9 May 2017)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M. S. & Ahsan, W. (2010). Int. J. Pharm. Sci. Drug Res. 2, 229-235.]; da Silva et al., 2001[Silva, J. F. M. da, Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]; Ramachandran, 2011[Ramachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289-294.]; Smitha et al., 2008[Smitha, S., Pandeya, S. N., Stables, J. P. & Ganapathy, S. (2008). Sci. Pharm. 76, 621-636.]). As part of our studies in this area, we have undertaken the synthesis and structure determination of the title compound (Fig. 1[link]).

[Figure 1]
Figure 1
The title mol­ecule with the atom-labelling scheme and 50% probability ellipsoids.

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[link]) connect the mol­ecules into zigzag chains running along the b-axis direction. The crystal packing is shown in Fig. 2[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯O1i 1.00 2.50 3.386 (2) 147
Symmetry code: (i) -x+1, y-1, -z.
[Figure 2]
Figure 2
The packing viewed down the b axis. C—H⋯O inter­actions are shown as dotted lines.

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 column chromatography 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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C23H26N4O7
Mr 470.48
Crystal system, space group Monoclinic, C2
Temperature (K) 150
a, b, c (Å) 25.6622 (8), 8.7731 (3), 10.3928 (3)
β (°) 101.847 (1)
V3) 2289.96 (13)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.86
Crystal size (mm) 0.18 × 0.18 × 0.09
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.86, 0.92
No. of measured, independent and observed [I > 2σ(I)] reflections 13935, 4250, 4142
Rint 0.028
(sin θ/λ)max−1) 0.619
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.064, 1.02
No. of reflections 4250
No. of parameters 312
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.15, −0.12
Absolute structure Flack x determined using 1738 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.06 (5)
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

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 top
Crystal data top
C23H26N4O7F(000) = 992
Mr = 470.48Dx = 1.365 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
a = 25.6622 (8) ÅCell parameters from 9918 reflections
b = 8.7731 (3) Åθ = 3.5–72.5°
c = 10.3928 (3) ŵ = 0.86 mm1
β = 101.847 (1)°T = 150 K
V = 2289.96 (13) Å3Thick plate, yellow
Z = 40.18 × 0.18 × 0.09 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
4250 independent reflections
Radiation source: INCOATEC IµS micro–focus source4142 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.028
Detector resolution: 10.4167 pixels mm-1θmax = 72.5°, θmin = 3.5°
ω scansh = 3131
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1010
Tmin = 0.86, Tmax = 0.92l = 1212
13935 measured reflections
Refinement top
Refinement on F2H-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) = 0.064Δρmax = 0.15 e Å3
S = 1.02Δρmin = 0.12 e Å3
4250 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
312 parametersExtinction coefficient: 0.00122 (12)
1 restraintAbsolute structure: Flack x determined using 1738 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sitesAbsolute structure parameter: 0.06 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.38504 (6)0.73451 (17)0.11559 (13)0.0422 (3)
O20.42118 (5)0.46504 (16)0.04958 (13)0.0361 (3)
O30.63848 (4)0.14283 (14)0.27385 (11)0.0256 (3)
O40.73597 (5)0.17670 (15)0.17487 (12)0.0318 (3)
O50.73377 (5)0.07332 (15)0.22667 (12)0.0306 (3)
O60.70228 (4)0.00891 (15)0.54268 (10)0.0273 (3)
O70.61358 (4)0.03958 (17)0.45789 (11)0.0308 (3)
N10.46396 (6)0.65011 (18)0.19074 (14)0.0285 (3)
N20.57957 (6)0.5944 (2)0.41853 (16)0.0361 (4)
N30.62799 (6)0.5552 (2)0.40657 (15)0.0351 (4)
N40.62257 (5)0.46388 (16)0.30101 (14)0.0263 (3)
C10.46996 (6)0.8105 (2)0.18610 (17)0.0275 (4)
C20.50002 (7)0.9035 (2)0.28016 (18)0.0327 (4)
H20.52120.86330.35860.039*
C30.49773 (7)1.0598 (2)0.2540 (2)0.0364 (4)
H30.51801.12700.31650.044*
C40.46679 (8)1.1205 (2)0.1399 (2)0.0378 (4)
H40.46571.22770.12670.045*
C50.43747 (7)1.0249 (2)0.04507 (18)0.0333 (4)
H50.41651.06510.03360.040*
C60.43983 (6)0.8696 (2)0.06881 (17)0.0284 (4)
C70.41433 (7)0.7402 (2)0.00880 (17)0.0306 (4)
C80.43274 (7)0.5968 (2)0.07729 (17)0.0289 (4)
C90.48516 (7)0.5535 (2)0.30425 (17)0.0308 (4)
H9A0.46640.45430.29360.037*
H9B0.47800.60250.38470.037*
C100.54375 (6)0.5266 (2)0.32078 (15)0.0277 (3)
C110.57112 (7)0.4422 (2)0.24590 (17)0.0276 (3)
H110.55680.38160.17130.033*
C120.66918 (6)0.3967 (2)0.26235 (17)0.0283 (3)
H12A0.70020.46510.28850.034*
H12B0.66230.38420.16570.034*
C130.68127 (6)0.2430 (2)0.32814 (15)0.0242 (3)
H130.68230.25490.42430.029*
C140.73352 (6)0.1746 (2)0.31067 (15)0.0252 (3)
H140.76410.23260.36350.030*
C150.73768 (6)0.0043 (2)0.34853 (15)0.0259 (3)
H150.77290.01710.40740.031*
C160.69277 (6)0.0520 (2)0.41186 (15)0.0253 (3)
H160.69230.16600.41430.030*
C170.63744 (6)0.0097 (2)0.34884 (15)0.0251 (3)
H170.61670.07120.29260.030*
C180.75196 (7)0.0290 (2)0.13954 (17)0.0307 (4)
C190.81202 (8)0.0232 (3)0.1570 (2)0.0419 (4)
H19A0.82840.04250.24930.063*
H19B0.82370.10110.10150.063*
H19C0.82280.07770.13140.063*
C200.72339 (10)0.0058 (3)0.00086 (19)0.0489 (5)
H20A0.73210.10960.02240.073*
H20B0.73460.06680.05970.073*
H20C0.68490.00270.00540.073*
C210.65171 (6)0.0218 (2)0.57957 (15)0.0286 (4)
C220.65193 (8)0.1628 (3)0.66276 (19)0.0388 (4)
H22A0.68200.15810.73810.058*
H22B0.61850.16850.69430.058*
H22C0.65540.25330.61000.058*
C230.63892 (7)0.1216 (2)0.64715 (18)0.0353 (4)
H23A0.63920.20900.58850.053*
H23B0.60360.11190.66870.053*
H23C0.66570.13700.72810.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0486 (8)0.0401 (8)0.0323 (7)0.0053 (6)0.0050 (6)0.0013 (6)
O20.0386 (7)0.0316 (7)0.0380 (7)0.0035 (5)0.0075 (5)0.0013 (5)
O30.0200 (5)0.0306 (7)0.0244 (5)0.0002 (4)0.0002 (4)0.0016 (5)
O40.0384 (7)0.0323 (7)0.0284 (6)0.0081 (5)0.0150 (5)0.0038 (5)
O50.0343 (6)0.0291 (6)0.0313 (6)0.0004 (5)0.0140 (5)0.0033 (5)
O60.0210 (5)0.0396 (7)0.0210 (5)0.0008 (5)0.0035 (4)0.0016 (5)
O70.0204 (5)0.0467 (8)0.0254 (5)0.0041 (5)0.0051 (4)0.0023 (5)
N10.0249 (7)0.0316 (8)0.0286 (7)0.0045 (6)0.0044 (5)0.0036 (6)
N20.0306 (7)0.0428 (10)0.0335 (8)0.0077 (7)0.0035 (6)0.0068 (7)
N30.0297 (7)0.0396 (9)0.0344 (8)0.0064 (6)0.0029 (6)0.0080 (7)
N40.0264 (7)0.0260 (7)0.0265 (6)0.0035 (5)0.0056 (5)0.0003 (6)
C10.0208 (7)0.0318 (9)0.0313 (9)0.0033 (6)0.0089 (6)0.0013 (7)
C20.0234 (7)0.0403 (10)0.0335 (8)0.0035 (7)0.0038 (7)0.0000 (8)
C30.0258 (8)0.0386 (11)0.0432 (10)0.0026 (7)0.0036 (7)0.0058 (8)
C40.0330 (9)0.0310 (10)0.0490 (11)0.0013 (7)0.0076 (8)0.0007 (8)
C50.0301 (8)0.0340 (10)0.0355 (9)0.0051 (7)0.0062 (7)0.0037 (8)
C60.0231 (7)0.0326 (9)0.0300 (8)0.0039 (7)0.0065 (6)0.0019 (7)
C70.0291 (8)0.0338 (9)0.0297 (8)0.0051 (7)0.0077 (7)0.0011 (7)
C80.0253 (7)0.0324 (10)0.0298 (8)0.0039 (7)0.0077 (6)0.0003 (7)
C90.0263 (8)0.0383 (10)0.0283 (8)0.0055 (7)0.0069 (6)0.0075 (7)
C100.0274 (8)0.0304 (9)0.0249 (7)0.0049 (7)0.0042 (6)0.0033 (7)
C110.0267 (7)0.0289 (9)0.0265 (7)0.0013 (6)0.0038 (6)0.0004 (6)
C120.0254 (7)0.0297 (9)0.0312 (8)0.0034 (7)0.0094 (6)0.0019 (7)
C130.0209 (7)0.0275 (8)0.0236 (7)0.0003 (6)0.0036 (6)0.0010 (6)
C140.0216 (7)0.0310 (9)0.0235 (7)0.0003 (6)0.0055 (6)0.0000 (6)
C150.0229 (7)0.0310 (9)0.0244 (7)0.0026 (6)0.0060 (6)0.0012 (7)
C160.0228 (7)0.0300 (9)0.0232 (7)0.0008 (6)0.0049 (6)0.0004 (6)
C170.0213 (7)0.0298 (8)0.0241 (7)0.0016 (6)0.0043 (6)0.0008 (7)
C180.0342 (8)0.0318 (9)0.0294 (8)0.0047 (7)0.0141 (7)0.0002 (7)
C190.0354 (9)0.0421 (11)0.0542 (11)0.0077 (8)0.0235 (8)0.0085 (10)
C200.0599 (13)0.0568 (14)0.0307 (9)0.0035 (11)0.0108 (9)0.0072 (10)
C210.0222 (7)0.0407 (10)0.0233 (7)0.0019 (7)0.0053 (6)0.0025 (7)
C220.0428 (10)0.0442 (11)0.0311 (9)0.0017 (9)0.0115 (8)0.0043 (8)
C230.0305 (8)0.0449 (11)0.0324 (9)0.0003 (8)0.0112 (7)0.0059 (8)
Geometric parameters (Å, º) top
O1—C71.207 (2)C9—H9A0.9900
O2—C81.213 (2)C9—H9B0.9900
O3—C171.408 (2)C10—C111.368 (2)
O3—C131.4290 (19)C11—H110.9500
O4—C141.4256 (19)C12—C131.515 (2)
O4—C181.430 (2)C12—H12A0.9900
O5—C181.420 (2)C12—H12B0.9900
O5—C151.423 (2)C13—C141.514 (2)
O6—C211.4313 (18)C13—H131.0000
O6—C161.4344 (19)C14—C151.543 (2)
O7—C171.4189 (19)C14—H141.0000
O7—C211.4396 (19)C15—C161.522 (2)
N1—C81.365 (2)C15—H151.0000
N1—C11.418 (2)C16—C171.535 (2)
N1—C91.464 (2)C16—H161.0000
N2—N31.319 (2)C17—H171.0000
N2—C101.359 (2)C18—C201.508 (3)
N3—N41.343 (2)C18—C191.515 (2)
N4—C111.341 (2)C19—H19A0.9800
N4—C121.462 (2)C19—H19B0.9800
C1—C21.381 (3)C19—H19C0.9800
C1—C61.402 (2)C20—H20A0.9800
C2—C31.396 (3)C20—H20B0.9800
C2—H20.9500C20—H20C0.9800
C3—C41.391 (3)C21—C221.508 (3)
C3—H30.9500C21—C231.510 (3)
C4—C51.392 (3)C22—H22A0.9800
C4—H40.9500C22—H22B0.9800
C5—C61.384 (3)C22—H22C0.9800
C5—H50.9500C23—H23A0.9800
C6—C71.467 (3)C23—H23B0.9800
C7—C81.560 (3)C23—H23C0.9800
C9—C101.497 (2)
C17—O3—C13113.08 (12)O4—C14—C13109.50 (13)
C14—O4—C18108.40 (13)O4—C14—C15104.49 (13)
C18—O5—C15107.02 (13)C13—C14—C15111.71 (13)
C21—O6—C16107.23 (11)O4—C14—H14110.3
C17—O7—C21110.78 (11)C13—C14—H14110.3
C8—N1—C1111.06 (14)C15—C14—H14110.3
C8—N1—C9123.58 (16)O5—C15—C16107.94 (13)
C1—N1—C9125.25 (15)O5—C15—C14104.35 (12)
N3—N2—C10108.73 (15)C16—C15—C14113.93 (13)
N2—N3—N4106.91 (14)O5—C15—H15110.1
C11—N4—N3111.19 (14)C16—C15—H15110.1
C11—N4—C12127.95 (15)C14—C15—H15110.1
N3—N4—C12120.80 (14)O6—C16—C15107.00 (13)
C2—C1—C6121.68 (17)O6—C16—C17103.62 (12)
C2—C1—N1127.68 (17)C15—C16—C17114.66 (14)
C6—C1—N1110.63 (16)O6—C16—H16110.4
C1—C2—C3116.58 (17)C15—C16—H16110.4
C1—C2—H2121.7C17—C16—H16110.4
C3—C2—H2121.7O3—C17—O7110.42 (14)
C4—C3—C2122.39 (18)O3—C17—C16114.07 (13)
C4—C3—H3118.8O7—C17—C16103.74 (12)
C2—C3—H3118.8O3—C17—H17109.5
C3—C4—C5120.29 (19)O7—C17—H17109.5
C3—C4—H4119.9C16—C17—H17109.5
C5—C4—H4119.9O5—C18—O4105.05 (12)
C6—C5—C4118.00 (17)O5—C18—C20108.82 (16)
C6—C5—H5121.0O4—C18—C20108.66 (16)
C4—C5—H5121.0O5—C18—C19111.23 (15)
C5—C6—C1121.01 (17)O4—C18—C19109.75 (16)
C5—C6—C7131.76 (17)C20—C18—C19112.99 (16)
C1—C6—C7107.22 (16)C18—C19—H19A109.5
O1—C7—C6131.38 (18)C18—C19—H19B109.5
O1—C7—C8123.52 (18)H19A—C19—H19B109.5
C6—C7—C8105.10 (14)C18—C19—H19C109.5
O2—C8—N1127.09 (17)H19A—C19—H19C109.5
O2—C8—C7126.99 (16)H19B—C19—H19C109.5
N1—C8—C7105.92 (15)C18—C20—H20A109.5
N1—C9—C10112.49 (14)C18—C20—H20B109.5
N1—C9—H9A109.1H20A—C20—H20B109.5
C10—C9—H9A109.1C18—C20—H20C109.5
N1—C9—H9B109.1H20A—C20—H20C109.5
C10—C9—H9B109.1H20B—C20—H20C109.5
H9A—C9—H9B107.8O6—C21—O7105.27 (11)
N2—C10—C11108.34 (15)O6—C21—C22108.76 (15)
N2—C10—C9121.73 (16)O7—C21—C22109.68 (16)
C11—C10—C9129.88 (16)O6—C21—C23110.75 (15)
N4—C11—C10104.82 (15)O7—C21—C23108.99 (14)
N4—C11—H11127.6C22—C21—C23113.10 (14)
C10—C11—H11127.6C21—C22—H22A109.5
N4—C12—C13109.77 (13)C21—C22—H22B109.5
N4—C12—H12A109.7H22A—C22—H22B109.5
C13—C12—H12A109.7C21—C22—H22C109.5
N4—C12—H12B109.7H22A—C22—H22C109.5
C13—C12—H12B109.7H22B—C22—H22C109.5
H12A—C12—H12B108.2C21—C23—H23A109.5
O3—C13—C14109.68 (14)C21—C23—H23B109.5
O3—C13—C12107.43 (13)H23A—C23—H23B109.5
C14—C13—C12113.77 (13)C21—C23—H23C109.5
O3—C13—H13108.6H23A—C23—H23C109.5
C14—C13—H13108.6H23B—C23—H23C109.5
C12—C13—H13108.6
C10—N2—N3—N40.4 (2)C17—O3—C13—C1471.36 (16)
N2—N3—N4—C110.8 (2)C17—O3—C13—C12164.51 (12)
N2—N3—N4—C12178.34 (16)N4—C12—C13—O367.01 (16)
C8—N1—C1—C2177.55 (17)N4—C12—C13—C14171.38 (14)
C9—N1—C1—C26.2 (3)C18—O4—C14—C13131.51 (15)
C8—N1—C1—C63.03 (19)C18—O4—C14—C1511.73 (16)
C9—N1—C1—C6173.24 (15)O3—C13—C14—O469.64 (17)
C6—C1—C2—C31.7 (3)C12—C13—C14—O450.70 (19)
N1—C1—C2—C3177.68 (17)O3—C13—C14—C1545.62 (17)
C1—C2—C3—C40.3 (3)C12—C13—C14—C15165.96 (13)
C2—C3—C4—C51.4 (3)C18—O5—C15—C16147.57 (14)
C3—C4—C5—C60.6 (3)C18—O5—C15—C1426.05 (16)
C4—C5—C6—C11.3 (3)O4—C14—C15—O58.66 (16)
C4—C5—C6—C7179.91 (18)C13—C14—C15—O5109.63 (14)
C2—C1—C6—C52.5 (3)O4—C14—C15—C16126.14 (13)
N1—C1—C6—C5176.93 (16)C13—C14—C15—C167.85 (18)
C2—C1—C6—C7178.58 (15)C21—O6—C16—C15152.78 (14)
N1—C1—C6—C71.97 (19)C21—O6—C16—C1731.24 (16)
C5—C6—C7—O11.4 (3)O5—C15—C16—O6171.12 (12)
C1—C6—C7—O1179.84 (19)C14—C15—C16—O673.50 (16)
C5—C6—C7—C8178.37 (18)O5—C15—C16—C1774.59 (18)
C1—C6—C7—C80.35 (18)C14—C15—C16—C1740.79 (19)
C1—N1—C8—O2178.09 (17)C13—O3—C17—O780.43 (15)
C9—N1—C8—O25.6 (3)C13—O3—C17—C1635.92 (18)
C1—N1—C8—C72.64 (17)C21—O7—C17—O3114.66 (15)
C9—N1—C8—C7173.71 (14)C21—O7—C17—C167.95 (19)
O1—C7—C8—O20.8 (3)O6—C16—C17—O396.50 (15)
C6—C7—C8—O2179.34 (17)C15—C16—C17—O319.7 (2)
O1—C7—C8—N1178.44 (17)O6—C16—C17—O723.67 (16)
C6—C7—C8—N11.39 (17)C15—C16—C17—O7139.92 (14)
C8—N1—C9—C10107.47 (19)C15—O5—C18—O433.89 (16)
C1—N1—C9—C1076.7 (2)C15—O5—C18—C20150.09 (15)
N3—N2—C10—C110.1 (2)C15—O5—C18—C1984.80 (17)
N3—N2—C10—C9177.57 (17)C14—O4—C18—O528.08 (17)
N1—C9—C10—N2107.04 (19)C14—O4—C18—C20144.40 (16)
N1—C9—C10—C1170.1 (3)C14—O4—C18—C1991.59 (16)
N3—N4—C11—C100.9 (2)C16—O6—C21—O726.73 (18)
C12—N4—C11—C10178.17 (16)C16—O6—C21—C22144.20 (14)
N2—C10—C11—N40.6 (2)C16—O6—C21—C2390.93 (16)
C9—C10—C11—N4176.84 (18)C17—O7—C21—O610.9 (2)
C11—N4—C12—C1386.2 (2)C17—O7—C21—C22127.73 (15)
N3—N4—C12—C1390.85 (19)C17—O7—C21—C23107.96 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O1i1.002.503.386 (2)147
Symmetry code: (i) x+1, y1, 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.

References

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