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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 2| Part 5| May 2017| x170739
https://doi.org/10.1107/S2414314617007398

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

CROSSMARK_Color_square_no_text.svg
Fatima-Zahrae Qachchachi,a Joel T. Mague,b Youssef Kandri Rodi,a Amal Haoudi,a* El Mestafa El Hadramia and El Mokhtar Essassic

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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 May 2017; accepted 19 May 2017; online 26 May 2017)

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.

CCDC reference: 1551162

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

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[Malhotra, S., Balwani, S., Dhawan, A., Singh, B. K., Kumar, S., Thimmulappa, R., Biswal, S., Olsen, C. E., Van der Eycken, E., Prasad, A. K., Ghosh, B. & Parmar, V. S. (2011). Med. Chem. Commun. 2, 743-751.]; Ramachandran, 2011[Ramachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289-294.]; Pandeya et al., 1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Med. Chem. 9, 25-31.]). 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[link]).

[Figure 1]
Figure 1
Perspective view of the mol­ecule with 50% probability displacement ellipsoids.

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[link]), mol­ecules are linked by weak C—H⋯O and C—H⋯N inter­actions (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

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-{\script{1\over 2}}, -z+2]; (ii) x, y+1, z.
[Figure 2]
Figure 2
Packing viewed down the b axis. H atoms have been omitted for clarity.

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 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 blocks 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 C23H25FN4O7
Mr 488.47
Crystal system, space group Monoclinic, P21
Temperature (K) 150
a, b, c (Å) 11.1688 (2), 9.0576 (2), 11.9237 (2)
β (°) 106.770 (1)
V (Å3) 1154.93 (4)
Z 2
Radiation type Cu Kα
μ (mm−1) 0.94
Crystal size (mm) 0.22 × 0.14 × 0.12
 
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 0.85, 0.90
No. of measured, independent and observed [I > 2σ(I)] reflections 8944, 4238, 4039
Rint 0.024
(sin θ/λ)max (Å−1) 0.618
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.074, 1.07
No. of reflections 4238
No. of parameters 320
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.16, −0.21
Absolute structure Flack x determined using 1689 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 −0.16 (7)
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.]), SHELXL2014 (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

CCDC reference: 1551162

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617007398/hb4145sup1.cif

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

checkCIF report


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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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 top
Crystal data top
C23H25FN4O7F(000) = 512
Mr = 488.47Dx = 1.405 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 11.1688 (2) ÅCell parameters from 7739 reflections
b = 9.0576 (2) Åθ = 3.9–72.4°
c = 11.9237 (2) ŵ = 0.94 mm−1
β = 106.770 (1)°T = 150 K
V = 1154.93 (4) Å3Block, yellow
Z = 20.22 × 0.14 × 0.12 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer		4238 independent reflections
Radiation source: INCOATEC IµS micro-focus source4039 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.024
Detector resolution: 10.4167 pixels mm-1θmax = 72.4°, θmin = 3.9°
ω scansh = −13→11
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		k = −10→10
Tmin = 0.85, Tmax = 0.90l = −14→14
8944 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-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 reflectionsΔρmax = 0.16 e Å−3
320 parametersΔρmin = −0.21 e Å−3
1 restraintAbsolute structure: Flack x determined using 1689 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.16 (7)
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 - 0.98 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
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)
O30.52752 (13)0.55460 (16)0.80812 (11)0.0251 (3)
O40.62417 (15)0.7676 (2)0.65424 (13)0.0366 (4)
O50.68733 (13)0.83262 (18)0.84705 (12)0.0284 (3)
O60.37527 (13)0.82992 (17)0.87562 (13)0.0285 (3)
O70.38313 (14)0.58384 (17)0.91212 (14)0.0318 (3)
N10.10525 (19)0.1240 (2)0.61668 (17)0.0342 (4)
N20.44173 (19)0.1415 (2)0.63368 (17)0.0328 (4)
N30.50589 (18)0.2619 (2)0.62900 (16)0.0308 (4)
N40.42566 (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)
H2−0.17640.34690.74540.046*
C3−0.0444 (2)0.2450 (2)0.68326 (19)0.0314 (5)
C40.0803 (2)0.1984 (3)0.71184 (19)0.0327 (5)
C50.1617 (2)0.2254 (3)0.8207 (2)0.0440 (6)
H50.24660.19490.84000.053*
C60.1150 (3)0.2991 (4)0.9015 (2)0.0507 (7)
H60.16870.32060.97740.061*
C7−0.1034 (2)0.1984 (3)0.5624 (2)0.0354 (5)
C80.0000 (2)0.1122 (3)0.5249 (2)0.0374 (5)
C90.2257 (2)0.0618 (3)0.6191 (2)0.0393 (5)
H9A0.2157−0.00170.54940.047*
H9B0.2562−0.00080.68960.047*
C100.3211 (2)0.1795 (2)0.62036 (18)0.0295 (5)
C110.3094 (2)0.3294 (2)0.60663 (18)0.0280 (4)
H110.23610.38750.59570.034*
C120.4715 (2)0.5241 (2)0.60179 (18)0.0268 (4)
H12A0.42340.56710.52580.032*
H12B0.56040.51870.60280.032*
C130.45991 (19)0.6235 (2)0.70029 (17)0.0237 (4)
H130.36980.63250.69730.028*
C140.51263 (19)0.7761 (2)0.69012 (17)0.0254 (4)
H140.44860.83720.63300.030*
C150.55554 (19)0.8558 (2)0.80891 (18)0.0244 (4)
H150.53620.96360.79890.029*
C160.50427 (19)0.7914 (2)0.90313 (17)0.0247 (4)
H160.55100.83160.98160.030*
C170.5044 (2)0.6209 (2)0.90607 (17)0.0259 (4)
H170.56800.58600.97880.031*
C180.3164 (2)0.7158 (3)0.92364 (19)0.0303 (5)
C190.1825 (2)0.7038 (3)0.8498 (2)0.0454 (6)
H19A0.18000.68340.76840.068*
H19B0.13910.79680.85350.068*
H19C0.14140.62330.87940.068*
C200.3298 (3)0.7443 (3)1.0523 (2)0.0410 (6)
H20A0.29410.66141.08460.061*
H20B0.28550.83541.06010.061*
H20C0.41860.75461.09520.061*
C210.7299 (2)0.8122 (3)0.74624 (18)0.0293 (4)
C220.8243 (3)0.6889 (4)0.7723 (3)0.0576 (8)
H22A0.78710.60080.79620.086*
H22B0.89780.71900.83570.086*
H22C0.84960.66670.70190.086*
C230.7782 (3)0.9559 (3)0.7127 (2)0.0521 (7)
H23A0.80530.94130.64230.078*
H23B0.84930.98970.77710.078*
H23C0.71161.03010.69700.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0725 (12)0.0748 (12)0.0426 (9)−0.0128 (10)0.0268 (8)−0.0144 (8)
O10.0361 (10)0.0514 (11)0.0391 (9)−0.0054 (8)−0.0041 (8)0.0050 (8)
O20.0608 (13)0.0598 (13)0.0431 (11)−0.0057 (10)0.0046 (9)−0.0193 (10)
O30.0290 (8)0.0241 (7)0.0210 (7)0.0040 (6)0.0053 (6)0.0022 (5)
O40.0339 (9)0.0505 (9)0.0282 (8)−0.0157 (7)0.0135 (7)−0.0091 (7)
O50.0225 (7)0.0365 (8)0.0251 (7)−0.0017 (6)0.0051 (5)−0.0014 (6)
O60.0260 (7)0.0271 (7)0.0334 (8)0.0013 (6)0.0103 (6)0.0016 (6)
O70.0352 (8)0.0272 (8)0.0373 (8)−0.0035 (6)0.0170 (7)−0.0001 (6)
N10.0331 (10)0.0325 (10)0.0337 (10)−0.0068 (8)0.0045 (8)−0.0002 (8)
N20.0359 (11)0.0280 (10)0.0345 (10)0.0043 (8)0.0099 (8)0.0009 (7)
N30.0335 (10)0.0292 (9)0.0299 (9)0.0051 (7)0.0092 (7)−0.0004 (7)
N40.0284 (9)0.0257 (9)0.0223 (8)0.0017 (7)0.0070 (7)−0.0024 (7)
C10.0537 (16)0.0478 (15)0.0340 (12)−0.0140 (12)0.0185 (11)−0.0038 (11)
C20.0396 (13)0.0344 (11)0.0401 (12)−0.0070 (10)0.0113 (10)0.0026 (10)
C30.0329 (12)0.0283 (11)0.0291 (11)−0.0082 (9)0.0025 (9)0.0029 (9)
C40.0328 (12)0.0334 (11)0.0293 (10)−0.0080 (9)0.0050 (9)0.0049 (9)
C50.0339 (13)0.0637 (18)0.0298 (11)−0.0094 (11)0.0020 (10)0.0028 (11)
C60.0490 (16)0.071 (2)0.0270 (12)−0.0193 (14)0.0031 (10)−0.0022 (12)
C70.0348 (13)0.0327 (11)0.0329 (11)−0.0094 (9)0.0005 (10)0.0045 (10)
C80.0416 (14)0.0323 (12)0.0341 (12)−0.0082 (9)0.0042 (10)−0.0004 (10)
C90.0401 (13)0.0284 (12)0.0490 (14)−0.0012 (10)0.0125 (11)0.0033 (10)
C100.0330 (12)0.0275 (11)0.0261 (10)0.0004 (8)0.0057 (9)−0.0005 (8)
C110.0284 (11)0.0265 (10)0.0287 (10)0.0007 (8)0.0074 (8)−0.0002 (9)
C120.0288 (11)0.0283 (11)0.0230 (9)−0.0028 (8)0.0072 (8)0.0006 (8)
C130.0229 (10)0.0255 (10)0.0205 (9)0.0010 (7)0.0029 (7)0.0026 (8)
C140.0256 (11)0.0269 (10)0.0221 (9)−0.0007 (8)0.0044 (8)0.0030 (8)
C150.0229 (10)0.0217 (10)0.0263 (10)−0.0016 (7)0.0036 (7)−0.0004 (8)
C160.0237 (10)0.0262 (11)0.0223 (9)0.0000 (7)0.0039 (8)−0.0019 (8)
C170.0308 (11)0.0255 (10)0.0209 (9)0.0009 (8)0.0067 (8)0.0024 (8)
C180.0306 (12)0.0286 (11)0.0339 (11)−0.0027 (8)0.0132 (9)−0.0015 (9)
C190.0295 (13)0.0516 (15)0.0547 (15)−0.0071 (11)0.0116 (11)−0.0023 (13)
C200.0485 (15)0.0424 (14)0.0384 (12)−0.0040 (11)0.0228 (11)−0.0029 (10)
C210.0272 (11)0.0346 (11)0.0267 (10)−0.0047 (9)0.0086 (8)−0.0027 (9)
C220.0545 (18)0.070 (2)0.0521 (16)0.0269 (15)0.0212 (13)0.0013 (15)
C230.0678 (19)0.0529 (17)0.0401 (14)−0.0308 (14)0.0225 (13)−0.0071 (12)
Geometric parameters (Å, º) top
F1—C11.362 (3)C9—H9A0.9900
O1—C71.204 (3)C9—H9B0.9900
O2—C81.209 (3)C10—C111.369 (3)
O3—C171.402 (2)C11—H110.9500
O3—C131.433 (2)C12—C131.515 (3)
O4—C211.419 (3)C12—H12A0.9900
O4—C141.431 (2)C12—H12B0.9900
O5—C151.425 (3)C13—C141.521 (3)
O5—C211.427 (2)C13—H131.0000
O6—C161.426 (2)C14—C151.538 (3)
O6—C181.430 (3)C14—H141.0000
O7—C171.418 (3)C15—C161.517 (3)
O7—C181.436 (3)C15—H151.0000
N1—C81.360 (3)C16—C171.545 (3)
N1—C41.415 (3)C16—H161.0000
N1—C91.451 (3)C17—H171.0000
N2—N31.315 (3)C18—C191.504 (3)
N2—C101.355 (3)C18—C201.521 (3)
N3—N41.343 (3)C19—H19A0.9800
N4—C111.348 (3)C19—H19B0.9800
N4—C121.455 (3)C19—H19C0.9800
C1—C21.372 (4)C20—H20A0.9800
C1—C61.375 (4)C20—H20B0.9800
C2—C31.383 (3)C20—H20C0.9800
C2—H20.9500C21—C221.505 (4)
C3—C41.400 (3)C21—C231.507 (3)
C3—C71.463 (3)C22—H22A0.9800
C4—C51.375 (3)C22—H22B0.9800
C5—C61.392 (4)C22—H22C0.9800
C5—H50.9500C23—H23A0.9800
C6—H60.9500C23—H23B0.9800
C7—C81.563 (4)C23—H23C0.9800
C9—C101.504 (3)
C17—O3—C13112.66 (15)O4—C14—C13111.41 (17)
C21—O4—C14110.83 (15)O4—C14—C15103.52 (16)
C15—O5—C21108.35 (15)C13—C14—C15112.20 (16)
C16—O6—C18106.35 (15)O4—C14—H14109.8
C17—O7—C18109.75 (15)C13—C14—H14109.8
C8—N1—C4111.0 (2)C15—C14—H14109.8
C8—N1—C9124.6 (2)O5—C15—C16106.43 (16)
C4—N1—C9124.41 (19)O5—C15—C14104.10 (16)
N3—N2—C10108.69 (18)C16—C15—C14114.71 (16)
N2—N3—N4107.15 (17)O5—C15—H15110.4
N3—N4—C11111.06 (18)C16—C15—H15110.4
N3—N4—C12119.04 (18)C14—C15—H15110.4
C11—N4—C12129.89 (18)O6—C16—C15107.93 (16)
F1—C1—C2118.7 (3)O6—C16—C17104.15 (16)
F1—C1—C6117.8 (2)C15—C16—C17113.75 (17)
C2—C1—C6123.5 (2)O6—C16—H16110.3
C1—C2—C3116.1 (2)C15—C16—H16110.3
C1—C2—H2122.0C17—C16—H16110.3
C3—C2—H2122.0O3—C17—O7110.45 (16)
C2—C3—C4121.6 (2)O3—C17—C16114.11 (16)
C2—C3—C7131.8 (2)O7—C17—C16104.05 (17)
C4—C3—C7106.7 (2)O3—C17—H17109.4
C5—C4—C3121.1 (2)O7—C17—H17109.4
C5—C4—N1127.7 (2)C16—C17—H17109.4
C3—C4—N1111.15 (18)O6—C18—O7104.61 (15)
C4—C5—C6117.4 (3)O6—C18—C19108.17 (19)
C4—C5—H5121.3O7—C18—C19109.86 (19)
C6—C5—H5121.3O6—C18—C20110.99 (18)
C1—C6—C5120.3 (2)O7—C18—C20109.60 (18)
C1—C6—H6119.9C19—C18—C20113.3 (2)
C5—C6—H6119.9C18—C19—H19A109.5
O1—C7—C3131.2 (2)C18—C19—H19B109.5
O1—C7—C8123.4 (2)H19A—C19—H19B109.5
C3—C7—C8105.41 (19)C18—C19—H19C109.5
O2—C8—N1127.8 (3)H19A—C19—H19C109.5
O2—C8—C7126.6 (2)H19B—C19—H19C109.5
N1—C8—C7105.63 (19)C18—C20—H20A109.5
N1—C9—C10112.0 (2)C18—C20—H20B109.5
N1—C9—H9A109.2H20A—C20—H20B109.5
C10—C9—H9A109.2C18—C20—H20C109.5
N1—C9—H9B109.2H20A—C20—H20C109.5
C10—C9—H9B109.2H20B—C20—H20C109.5
H9A—C9—H9B107.9O4—C21—O5106.43 (16)
N2—C10—C11108.8 (2)O4—C21—C22109.0 (2)
N2—C10—C9119.9 (2)O5—C21—C22107.85 (19)
C11—C10—C9131.2 (2)O4—C21—C23108.8 (2)
N4—C11—C10104.28 (19)O5—C21—C23110.09 (19)
N4—C11—H11127.9C22—C21—C23114.3 (2)
C10—C11—H11127.9C21—C22—H22A109.5
N4—C12—C13111.82 (16)C21—C22—H22B109.5
N4—C12—H12A109.3H22A—C22—H22B109.5
C13—C12—H12A109.3C21—C22—H22C109.5
N4—C12—H12B109.3H22A—C22—H22C109.5
C13—C12—H12B109.3H22B—C22—H22C109.5
H12A—C12—H12B107.9C21—C23—H23A109.5
O3—C13—C12107.23 (16)C21—C23—H23B109.5
O3—C13—C14110.57 (16)H23A—C23—H23B109.5
C12—C13—C14110.90 (16)C21—C23—H23C109.5
O3—C13—H13109.4H23A—C23—H23C109.5
C12—C13—H13109.4H23B—C23—H23C109.5
C14—C13—H13109.4
C10—N2—N3—N4−0.3 (2)C11—N4—C12—C1364.1 (3)
N2—N3—N4—C110.4 (2)C17—O3—C13—C12−168.58 (16)
N2—N3—N4—C12−179.12 (17)C17—O3—C13—C1470.4 (2)
F1—C1—C2—C3179.1 (2)N4—C12—C13—O357.2 (2)
C6—C1—C2—C30.3 (4)N4—C12—C13—C14177.97 (17)
C1—C2—C3—C41.1 (3)C21—O4—C14—C13−111.73 (19)
C1—C2—C3—C7178.9 (2)C21—O4—C14—C159.1 (2)
C2—C3—C4—C5−1.6 (4)O3—C13—C14—O479.27 (19)
C7—C3—C4—C5−179.9 (2)C12—C13—C14—O4−39.5 (2)
C2—C3—C4—N1178.1 (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—C5177.1 (2)C21—O5—C15—C16148.22 (17)
C9—N1—C4—C50.0 (4)C21—O5—C15—C1426.7 (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—O598.75 (18)
C3—C4—C5—C60.7 (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—C15151.56 (16)
C2—C1—C6—C5−1.1 (4)C18—O6—C16—C1730.35 (19)
C4—C5—C6—C10.6 (4)O5—C15—C16—O6172.38 (15)
C2—C3—C7—O14.5 (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—C1741.9 (2)
C4—C3—C7—C82.5 (2)C13—O3—C17—O773.2 (2)
C4—N1—C8—O2−174.8 (3)C13—O3—C17—C16−43.6 (2)
C9—N1—C8—O22.2 (4)C18—O7—C17—O3−128.04 (17)
C4—N1—C8—C74.0 (2)C18—O7—C17—C16−5.2 (2)
C9—N1—C8—C7−178.9 (2)O6—C16—C17—O3105.06 (18)
O1—C7—C8—O2−5.2 (4)C15—C16—C17—O3−12.2 (3)
C3—C7—C8—O2174.8 (2)O6—C16—C17—O7−15.4 (2)
O1—C7—C8—N1176.0 (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—C10112.8 (2)C16—O6—C18—C19−150.96 (19)
C4—N1—C9—C10−70.5 (3)C16—O6—C18—C2084.2 (2)
N3—N2—C10—C110.1 (2)C17—O7—C18—O623.9 (2)
N3—N2—C10—C9178.42 (19)C17—O7—C18—C19139.75 (19)
N1—C9—C10—N2173.84 (19)C17—O7—C18—C20−95.2 (2)
N1—C9—C10—C11−8.3 (4)C14—O4—C21—O56.9 (2)
N3—N4—C11—C10−0.3 (2)C14—O4—C21—C22123.0 (2)
C12—N4—C11—C10179.12 (19)C14—O4—C21—C23−111.7 (2)
N2—C10—C11—N40.1 (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—C2396.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.952.243.184 (3)170
C15—H15···N2ii1.002.533.338 (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.

References

First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationMalhotra, S., Balwani, S., Dhawan, A., Singh, B. K., Kumar, S., Thimmulappa, R., Biswal, S., Olsen, C. E., Van der Eycken, E., Prasad, A. K., Ghosh, B. & Parmar, V. S. (2011). Med. Chem. Commun. 2, 743–751.  Web of Science CrossRef CAS Google Scholar
 First citationPandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Med. Chem. 9, 25–31.  CAS Google Scholar
 First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationRamachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289–294.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 2| Part 5| May 2017| x170739
https://doi.org/10.1107/S2414314617007398
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