3-Hy­droxy-3-(2-oxo-2,3-di­hydro-1H-indol-3-yl)-2,3-di­hydro-1H-indol-2-one

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Adam, M.S.S.; Hawaiz, F.E.

doi:10.1107/S2414314617001390

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170139

https://doi.org/10.1107/S2414314617001390

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3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Mohamed Shaker S. Adam ^e and Farouq E. Hawaiz ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, Sohag-82534, Egypt, and ^fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 24 January 2017; accepted 27 January 2017; online 3 February 2017)

The conformation of the title molecule, C₁₆H₁₂N₂O₃, is partly determined by an intramolecular C=O⋯π interaction between one carbonyl group and the five-membered ring of the other indolinone moiety. The crystal packing consists of layers parallel to (001) formed by a combination of N—H⋯O and O—H⋯O hydrogen bonds and π–π stacking interactions. Both the N—H⋯O and O—H⋯O hydrogen bonds generate inversion dimers.

Keywords: crystal structure; hydrogen bond; π–π stacking; indolinone; isatin; dimerization.

CCDC reference: 1529856

Structure description

Indole scaffold compounds are synthetically important substrates that can be used for the synthesis of a large variety of heterocyclic compounds, and as raw material for drug synthesis (Grewal, 2014 ). Recently, isatin derivatives have attracted strong interest in organic and medicinal chemistry due to their potent biological and pharmacological activities including antitumor (Premanathan et al., 2012 ; Havrylyuk et al., 2011 ), antimicrobial (Singh et al., 2010 ; Ali & Alam, 1994 ; Pandeya et al., 1999b ), anti-inflammatory and analgesic (Abele et al., 2003 ; Mondal, et al., 2010 ), antimycobacterial (Aboul-Fadl et al., 2010 ; Sriram et al., 2006 ), anticonvulsant (Malawska, 2005 ), antiviral (Selvam et al., 2006 ; Selvam et al., 2008 ; Abbas et al., 2013 ), anthelmintic (Suresh et al., 2011 ), anti-HIV applications (Pandeya et al., 1999a ) and anti-oxidant (Andreani et al., 2010 ; Kiran et al. 2013 ). In this context, the present study reports the synthesis and crystal structure determination of the title bis-indole derivative.

In the title compound (Fig. 1), the indolinone moieties are close to being planar, with r.m.s. deviations of the nine atoms from the mean plane being 0.025 Å for the ring system containing atom N1 and 0.014 Å for that containing atom N2. The dihedral angle between the mean planes of the two indolinone moieties is 58.69 (3)°. The conformation of the molecule is determined in part by a C=O⋯π interaction between the C10=O3 carbonyl group and the C1/C6/C7/C8/N1 ring (Fig. 1 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1,C6,C7,C8,N1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.84	1.93	2.7575 (17)	167
N1—H1⋯O3ⁱⁱ	0.94 (2)	1.96 (2)	2.8644 (17)	161 (2)
N2—H2B⋯O3ⁱⁱⁱ	0.90 (3)	2.00 (3)	2.8882 (18)	173 (2)
C10—O3⋯Cg1	1.24 (1)	2.92 (1)	3.0414 (13)	73 (1)
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+1.

Figure 1
The title molecule with the atom-labeling scheme and 50% probability ellipsoids. The C=O⋯π(ring) interaction is shown as a dotted line. Cg1 is the centroid of the C1/C6/C7/C8/N1 ring.

The bond lengths and angles of the title compound are comparable with those reported for related compounds such as (3E)-3-[(4-butylphenyl)imino]-1,3-dihydro-2H-indol-2-one (Akkurt et al., 2003 ), 2-oxo-2,3-dihydro-1H-indol-3-one nicotinoylhydrazone (Ali et al., 2005 ) and 3-(2-amino-1-methyl-4-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxy-1-phenylindolin-2-one ethanol solvate (Penthala et al., 2009 ).

The N2—H2B⋯O3 and the O2—H2A⋯O1 hydrogen bonds (Table 1) generate inversion dimers with R₂²(8) and R₂²(10) ring motifs, respectively (Fig. 2). The other N1—H1⋯O3 contact also forms an inversion dimer but, in this case, with an R₂²(14) motif. A combination of N1—H1⋯O3 and N2—H2B⋯O3 hydrogen bonds generate zigzag chains of molecules running parallel to the b-axis direction which are formed into sheets parallel to (001) by pairwise O2—H2A⋯O1 hydrogen bonds (Figs. 2 and 3). The layer formation is assisted by complementary π–π stacking interactions [Cg2⋯Cg3 = 3.571 (1) Å] between the C11–C16 and C16/C9/C10/C11/N2 rings (Fig. 4).

Figure 2
Detail of the O—H⋯O (red dotted lines) and N—H⋯O (blue dotted lines) hydrogen bonds. [Symmetry codes: (ii) 1 − x, 1 − y, 1 − z; (iii) 1 − x, 2 − y, 1 − z; (iv) 2 − x, 2 − y, 1 − z.]

Figure 3
Packing showing one of the N—H⋯O hydrogen bonded (blue dotted lines) chains.

Figure 4
Details of the π–π stacking interactions. Cg2 and Cg3 are the centroids of the C9/C10/N3/C11/C16 and C11–C16 rings, respectively. [Symmetry code: (i) 2 − x, 1 − y, 1 − z.]

Synthesis and crystallization

The title compound was obtained (Fig. 5) as a major product during an an attempt to synthesize a new tridentate ONO-dibasic hydrazone (1) derived from the condensation of phenyl alanine with isatin by the following procedures:

Figure 5
A scheme showing the reaction leading to the formation of the title compound.

A methanolic solution (15 ml) of isatin (1 mmol) was added dropwise to an aqueous/methanolic (1:1) (10 ml) solution of phenyl alanine at room temperature. The reaction mixture was refluxed at 353 K (monitored by TLC) for 2 h, resulting in the formation of a dark-red precipitate. The precipitate was extracted by filtration and washed many times with water and diethyl ether then dried in an oven. The final product was recystallized in hot methanol to furnish good quality dark-red crystals of 3-hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one (2) in 84% yield. Phenyl alanine may act as a Lewis base to activate the isatin causing dimerization in the aqueous/methanolic media.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydroxyl hydrogen did not refine satisfactorily although definitely located in a difference map, possibly due to unresolved disorder. Consequently it was placed in a calculated position (SHELXL HFIX 147 instruction) and included as a riding contribution.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₃
M_r	280.28
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	7.7193 (3), 8.6977 (3), 9.5907 (4)
α, β, γ (°)	90.457 (2), 95.070 (2), 90.627 (2)
V (Å³)	641.34 (4)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.84
Crystal size (mm)	0.14 × 0.07 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.89, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	8464, 2487, 2137
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.06
No. of reflections	2487
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1529856

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617001390/sj4085sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001390/sj4085Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001390/sj4085Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); 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).

3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one top

Crystal data top

C₁₆H₁₂N₂O₃	Z = 2
M_r = 280.28	F(000) = 292
Triclinic, P1	D_x = 1.451 Mg m⁻³
a = 7.7193 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.6977 (3) Å	Cell parameters from 6334 reflections
c = 9.5907 (4) Å	θ = 4.6–72.4°
α = 90.457 (2)°	µ = 0.84 mm⁻¹
β = 95.070 (2)°	T = 150 K
γ = 90.627 (2)°	Column, dark yellow-orange
V = 641.34 (4) Å³	0.14 × 0.07 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2487 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2137 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 4.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
T_min = 0.89, T_max = 0.96	l = −11→11
8464 measured reflections

Refinement top

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)] = 0.039	Hydrogen site location: mixed
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.043P)² + 0.3252P] where P = (F_o² + 2F_c²)/3
2487 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

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. The hydroxyl hydrogen did not refine satisfactorily although definitely located in a difference map, possibly due to unresolved disorder. Consequently it was placed in a calculated position (SHELXL HFIX 147 instruction) and included as a riding contribution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.78629 (14)	1.05555 (13)	0.52109 (12)	0.0311 (3)
O2	0.94772 (15)	0.94251 (13)	0.26711 (13)	0.0311 (3)
H2A	1.0265	0.9586	0.3319	0.047*
O3	0.58356 (14)	0.70275 (12)	0.52877 (12)	0.0272 (3)
N1	0.56106 (17)	1.03152 (15)	0.34911 (14)	0.0252 (3)
H1	0.491 (3)	1.105 (3)	0.388 (2)	0.052 (6)*
N2	0.69437 (18)	0.50298 (15)	0.40763 (14)	0.0248 (3)
H2B	0.613 (3)	0.433 (3)	0.423 (2)	0.051 (6)*
C1	0.5182 (2)	0.93711 (17)	0.23090 (16)	0.0243 (3)
C2	0.3649 (2)	0.9328 (2)	0.14575 (18)	0.0306 (4)
H2	0.266 (3)	1.000 (2)	0.162 (2)	0.033 (5)*
C3	0.3529 (2)	0.8279 (2)	0.03503 (19)	0.0341 (4)
H3	0.246 (3)	0.824 (2)	−0.025 (2)	0.042 (6)*
C4	0.4899 (2)	0.7319 (2)	0.01088 (18)	0.0334 (4)
H4	0.474 (3)	0.656 (2)	−0.070 (2)	0.037 (5)*
C5	0.6447 (2)	0.73867 (19)	0.09783 (17)	0.0281 (4)
H5	0.743 (3)	0.672 (2)	0.084 (2)	0.033 (5)*
C6	0.6578 (2)	0.84201 (17)	0.20856 (16)	0.0230 (3)
C7	0.80112 (19)	0.87379 (17)	0.32288 (16)	0.0224 (3)
C8	0.71796 (19)	0.99649 (17)	0.41294 (17)	0.0239 (3)
C9	0.85503 (19)	0.73274 (17)	0.41305 (16)	0.0225 (3)
H9	0.928 (2)	0.7736 (19)	0.5023 (18)	0.022 (4)*
C10	0.69513 (19)	0.64824 (17)	0.45866 (16)	0.0222 (3)
C11	0.8409 (2)	0.47612 (17)	0.33341 (16)	0.0233 (3)
C12	0.8850 (2)	0.34313 (19)	0.26664 (18)	0.0289 (4)
H12	0.812 (3)	0.251 (2)	0.267 (2)	0.033 (5)*
C13	1.0385 (2)	0.3456 (2)	0.20033 (19)	0.0326 (4)
H13	1.073 (3)	0.257 (2)	0.153 (2)	0.039 (5)*
C14	1.1432 (2)	0.4764 (2)	0.20282 (19)	0.0336 (4)
H14	1.251 (3)	0.476 (2)	0.159 (2)	0.039 (5)*
C15	1.0967 (2)	0.6096 (2)	0.27092 (18)	0.0288 (4)
H15	1.169 (2)	0.701 (2)	0.273 (2)	0.031 (5)*
C16	0.94318 (19)	0.60941 (17)	0.33510 (16)	0.0229 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0273 (6)	0.0304 (6)	0.0357 (7)	−0.0045 (5)	0.0043 (5)	−0.0121 (5)
O2	0.0265 (6)	0.0299 (6)	0.0382 (7)	−0.0054 (5)	0.0111 (5)	−0.0011 (5)
O3	0.0281 (6)	0.0223 (5)	0.0331 (6)	0.0003 (4)	0.0133 (5)	−0.0023 (4)
N1	0.0236 (6)	0.0220 (6)	0.0306 (7)	0.0002 (5)	0.0065 (5)	−0.0039 (5)
N2	0.0262 (7)	0.0193 (6)	0.0302 (7)	−0.0027 (5)	0.0102 (5)	−0.0015 (5)
C1	0.0257 (8)	0.0217 (7)	0.0265 (8)	−0.0028 (6)	0.0076 (6)	−0.0003 (6)
C2	0.0259 (8)	0.0344 (9)	0.0321 (9)	0.0018 (7)	0.0057 (7)	0.0022 (7)
C3	0.0291 (8)	0.0430 (10)	0.0297 (9)	−0.0039 (7)	−0.0001 (7)	0.0009 (7)
C4	0.0391 (9)	0.0346 (9)	0.0263 (9)	−0.0015 (7)	0.0021 (7)	−0.0041 (7)
C5	0.0326 (8)	0.0258 (8)	0.0265 (8)	0.0017 (7)	0.0058 (6)	−0.0016 (6)
C6	0.0235 (7)	0.0203 (7)	0.0258 (8)	−0.0031 (6)	0.0058 (6)	0.0016 (6)
C7	0.0202 (7)	0.0195 (7)	0.0283 (8)	−0.0042 (6)	0.0075 (6)	−0.0019 (6)
C8	0.0229 (7)	0.0187 (7)	0.0310 (8)	−0.0052 (6)	0.0086 (6)	−0.0018 (6)
C9	0.0203 (7)	0.0214 (7)	0.0263 (8)	−0.0015 (6)	0.0050 (6)	−0.0033 (6)
C10	0.0233 (7)	0.0203 (7)	0.0235 (7)	−0.0001 (6)	0.0043 (6)	0.0001 (6)
C11	0.0247 (7)	0.0222 (7)	0.0236 (8)	0.0018 (6)	0.0053 (6)	0.0004 (6)
C12	0.0358 (9)	0.0218 (8)	0.0298 (8)	0.0012 (7)	0.0074 (7)	−0.0013 (6)
C13	0.0384 (9)	0.0281 (9)	0.0327 (9)	0.0070 (7)	0.0100 (7)	−0.0042 (7)
C14	0.0296 (9)	0.0364 (9)	0.0367 (9)	0.0052 (7)	0.0127 (7)	−0.0032 (7)
C15	0.0237 (8)	0.0287 (8)	0.0347 (9)	−0.0005 (7)	0.0067 (6)	−0.0019 (7)
C16	0.0226 (7)	0.0213 (7)	0.0250 (7)	0.0010 (6)	0.0030 (6)	−0.0014 (6)

Geometric parameters (Å, º) top

O1—C8	1.2275 (19)	C5—C6	1.382 (2)
O2—C7	1.4217 (18)	C5—H5	0.97 (2)
O2—H2A	0.8400	C6—C7	1.509 (2)
O3—C10	1.2348 (18)	C7—C9	1.546 (2)
N1—C8	1.347 (2)	C7—C8	1.548 (2)
N1—C1	1.408 (2)	C9—C16	1.505 (2)
N1—H1	0.94 (2)	C9—C10	1.528 (2)
N2—C10	1.3510 (19)	C9—H9	1.039 (17)
N2—C11	1.4091 (19)	C11—C12	1.378 (2)
N2—H2B	0.90 (3)	C11—C16	1.395 (2)
C1—C2	1.378 (2)	C12—C13	1.394 (2)
C1—C6	1.396 (2)	C12—H12	0.97 (2)
C2—C3	1.391 (3)	C13—C14	1.387 (3)
C2—H2	0.99 (2)	C13—H13	0.95 (2)
C3—C4	1.388 (3)	C14—C15	1.392 (2)
C3—H3	0.97 (2)	C14—H14	0.97 (2)
C4—C5	1.396 (2)	C15—C16	1.383 (2)
C4—H4	1.02 (2)	C15—H15	0.96 (2)

C7—O2—H2A	109.5	O1—C8—N1	126.03 (14)
C8—N1—C1	111.47 (13)	O1—C8—C7	125.72 (14)
C8—N1—H1	120.7 (14)	N1—C8—C7	108.20 (13)
C1—N1—H1	127.6 (14)	C16—C9—C10	102.45 (12)
C10—N2—C11	111.35 (13)	C16—C9—C7	113.88 (13)
C10—N2—H2B	123.3 (14)	C10—C9—C7	110.84 (12)
C11—N2—H2B	125.3 (14)	C16—C9—H9	114.1 (9)
C2—C1—C6	122.38 (15)	C10—C9—H9	108.2 (10)
C2—C1—N1	127.82 (14)	C7—C9—H9	107.2 (9)
C6—C1—N1	109.80 (14)	O3—C10—N2	125.26 (14)
C1—C2—C3	117.15 (16)	O3—C10—C9	126.29 (14)
C1—C2—H2	122.0 (11)	N2—C10—C9	108.44 (13)
C3—C2—H2	120.9 (11)	C12—C11—C16	122.28 (15)
C4—C3—C2	121.50 (16)	C12—C11—N2	128.31 (15)
C4—C3—H3	120.7 (12)	C16—C11—N2	109.41 (13)
C2—C3—H3	117.8 (12)	C11—C12—C13	117.30 (16)
C3—C4—C5	120.50 (16)	C11—C12—H12	120.7 (11)
C3—C4—H4	118.5 (11)	C13—C12—H12	121.9 (11)
C5—C4—H4	121.0 (11)	C14—C13—C12	121.20 (15)
C6—C5—C4	118.51 (15)	C14—C13—H13	118.8 (13)
C6—C5—H5	119.3 (11)	C12—C13—H13	119.9 (13)
C4—C5—H5	122.2 (11)	C13—C14—C15	120.69 (16)
C5—C6—C1	119.95 (15)	C13—C14—H14	120.5 (12)
C5—C6—C7	131.78 (14)	C15—C14—H14	118.8 (12)
C1—C6—C7	108.24 (13)	C16—C15—C14	118.65 (16)
O2—C7—C6	110.72 (12)	C16—C15—H15	120.3 (11)
O2—C7—C9	111.02 (12)	C14—C15—H15	121.0 (11)
C6—C7—C9	114.49 (12)	C15—C16—C11	119.85 (14)
O2—C7—C8	107.89 (12)	C15—C16—C9	131.84 (14)
C6—C7—C8	102.04 (12)	C11—C16—C9	108.31 (13)
C9—C7—C8	110.15 (12)

C8—N1—C1—C2	175.44 (16)	C6—C7—C9—C16	67.76 (16)
C8—N1—C1—C6	−4.44 (19)	C8—C7—C9—C16	−177.95 (12)
C6—C1—C2—C3	0.4 (2)	O2—C7—C9—C10	−173.39 (12)
N1—C1—C2—C3	−179.48 (16)	C6—C7—C9—C10	−47.12 (17)
C1—C2—C3—C4	−0.3 (3)	C8—C7—C9—C10	67.17 (15)
C2—C3—C4—C5	−0.2 (3)	C11—N2—C10—O3	−179.33 (14)
C3—C4—C5—C6	0.4 (3)	C11—N2—C10—C9	1.48 (17)
C4—C5—C6—C1	−0.3 (2)	C16—C9—C10—O3	178.65 (15)
C4—C5—C6—C7	177.50 (16)	C7—C9—C10—O3	−59.5 (2)
C2—C1—C6—C5	−0.1 (2)	C16—C9—C10—N2	−2.16 (16)
N1—C1—C6—C5	179.79 (14)	C7—C9—C10—N2	119.69 (14)
C2—C1—C6—C7	−178.38 (15)	C10—N2—C11—C12	−179.90 (16)
N1—C1—C6—C7	1.50 (17)	C10—N2—C11—C16	−0.08 (18)
C5—C6—C7—O2	68.9 (2)	C16—C11—C12—C13	0.4 (2)
C1—C6—C7—O2	−113.13 (14)	N2—C11—C12—C13	−179.79 (16)
C5—C6—C7—C9	−57.6 (2)	C11—C12—C13—C14	0.6 (3)
C1—C6—C7—C9	120.45 (14)	C12—C13—C14—C15	−0.6 (3)
C5—C6—C7—C8	−176.54 (17)	C13—C14—C15—C16	−0.5 (3)
C1—C6—C7—C8	1.48 (15)	C14—C15—C16—C11	1.5 (2)
C1—N1—C8—O1	−177.15 (15)	C14—C15—C16—C9	−178.43 (16)
C1—N1—C8—C7	5.31 (17)	C12—C11—C16—C15	−1.5 (2)
O2—C7—C8—O1	−65.0 (2)	N2—C11—C16—C15	178.67 (14)
C6—C7—C8—O1	178.37 (15)	C12—C11—C16—C9	178.46 (15)
C9—C7—C8—O1	56.38 (19)	N2—C11—C16—C9	−1.37 (17)
O2—C7—C8—N1	112.59 (14)	C10—C9—C16—C15	−177.95 (17)
C6—C7—C8—N1	−4.09 (15)	C7—C9—C16—C15	62.3 (2)
C9—C7—C8—N1	−126.08 (13)	C10—C9—C16—C11	2.10 (16)
O2—C7—C9—C16	−58.50 (16)	C7—C9—C16—C11	−117.65 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1,C6,C7,C8,N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.84	1.93	2.7575 (17)	167
N1—H1···O3ⁱⁱ	0.94 (2)	1.96 (2)	2.8644 (17)	161 (2)
N2—H2B···O3ⁱⁱⁱ	0.90 (3)	2.00 (3)	2.8882 (18)	173 (2)
C10—O3···Cg1	1.24 (1)	2.92 (1)	3.0414 (13)	73 (1)

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

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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