(E)-N′-Benzyl­idene-2-phenyl­quinoline-4-carbo­hydrazide

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Albayati, M.R.; Ahmed, E.A.

doi:10.1107/S2414314616015443

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161544

https://doi.org/10.1107/S2414314616015443

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(E)-N′-Benzylidene-2-phenylquinoline-4-carbohydrazide

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Mustafa R. Albayati ^e and Ehab A. Ahmed ^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, ^eKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq, and ^fDepartment of Chemistry, College of Education, Tikrit University, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 September 2016; accepted 2 October 2016; online 18 October 2016)

In the title compound, C₂₃H₁₇N₃O, there is a short intramolecular C—H⋯O contact present, and the conformation about the C=N bond is E. The phenyl and benzylidene rings make dihedral angles of 28.21 (15) and 37.65 (14)° with the mean plane of the quinoline moiety. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [001], with the O atom accepting three hydrogen bonds.

Keywords: crystal structure; quinoline; carbohydrazide; hydrogen bonding.

CCDC reference: 1507748

Structure description

It has been reported that quinoline derivatives serve as antagonists (Bennacef et al., 2007 ), analgesic agents (Gopalsamy & Pallai, 1997 ), 5HT3 antagonists (Anzini et al., 1995 ) and structural subunits of natural products (Sivaprasad et al., 2006 ). Among the compounds of a quinoline series, Atophan and its derivatives have shown a variety of biological effects (Muscia et al., 2008 ; Wang et al., 2009 ). Moreover, hydrazide-hydrazone compounds are found to be associated with various biological activities such as antimicrobial, anticonvulsant, analgesic, anti-inflammatory, anti-platelet, anti-tubercular and anti-tumour properties (Mohamed et al., 2015 ). As part of our studies in this area, we now report the crystal structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. The quinoline moiety is slightly twisted as indicated by the dihedral angle of 2.27 (16)° between the C1–C6 and N1/C6–C9 rings. The phenyl (C10–C15) and benzylidene (C18–C23) rings make dihedral angles of 28.21 (15) and 37.65 (14)°, respectively, with the mean plane of the quinoline moiety. The conformation about the C17=N3 bond is E and there is a short C5—H5⋯O1 contact in the molecule (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.95	2.34	2.939 (3)	121
N2—H2A⋯O1ⁱ	0.88 (4)	2.08 (4)	2.907 (3)	155 (4)
C8—H8⋯O1ⁱ	0.95	2.50	3.288 (3)	140
C17—H17⋯O1ⁱ	0.95	2.52	3.268 (3)	136
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids.

In the crystal, N2—H2A⋯O1ⁱ, C8—H8⋯O1ⁱ and C17—H17⋯O1ⁱ [symmetry code: (i) x, −y + 1, z − $[{1\over 2}]$ ] hydrogen bonds link the molecules into chains along the c-axis direction (Table 1 and Fig. 2).

Figure 2
A view along the a axis of the crystal packing of the title compound. The N—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

) and, for clarity, only H atoms H26, H8 and H17 have been included.

Synthesis and crystallization

The title compound was prepared in 89% yield according to a reported procedure (Mohamed et al., 2016 ). Colourless needle-like crystals of the title compound were obtained by recrystallization from ethanol solution (m.p. 515–518 K).

Refinement

Crystal and refinement details are given in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O
M_r	351.39
Crystal system, space group	Monoclinic, Pc
Temperature (K)	150
a, b, c (Å)	7.6704 (8), 13.2898 (13), 9.0627 (9)
β (°)	107.220 (6)
V (Å³)	882.42 (16)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.66
Crystal size (mm)	0.24 × 0.07 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.83, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	6668, 2637, 2394
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.087, 1.07
No. of reflections	2637
No. of parameters	250
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ), Mercury (Macrae et al., 2008 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1507748

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616015443/su4080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015443/su4080Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616015443/su4080Isup3.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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-N'-Benzylidene-2-phenylquinoline-4-carbohydrazide top

Crystal data top

C₂₃H₁₇N₃O	F(000) = 368
M_r = 351.39	D_x = 1.323 Mg m⁻³
Monoclinic, Pc	Cu Kα radiation, λ = 1.54178 Å
a = 7.6704 (8) Å	Cell parameters from 5448 reflections
b = 13.2898 (13) Å	θ = 3.3–72.3°
c = 9.0627 (9) Å	µ = 0.66 mm⁻¹
β = 107.220 (6)°	T = 150 K
V = 882.42 (16) Å³	Needles, colourless
Z = 2	0.24 × 0.07 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2637 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2394 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 3.3°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −16→15
T_min = 0.83, T_max = 0.97	l = −10→11
6668 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0333P)² + 0.1673P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.087	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.16 e Å⁻³
2637 reflections	Δρ_min = −0.16 e Å⁻³
250 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0046 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.2 (4)

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
O1	0.5328 (3)	0.41857 (14)	0.9098 (2)	0.0351 (5)
N1	0.3365 (4)	0.19467 (18)	0.4307 (3)	0.0312 (5)
N2	0.6135 (4)	0.50398 (17)	0.7228 (3)	0.0296 (5)
H2A	0.604 (5)	0.510 (3)	0.624 (4)	0.045 (10)*
N3	0.6784 (3)	0.58400 (17)	0.8203 (3)	0.0296 (5)
C1	0.4132 (4)	0.1685 (2)	0.5821 (3)	0.0290 (6)
C2	0.4235 (4)	0.0645 (2)	0.6177 (3)	0.0344 (7)
H2	0.3728	0.0170	0.5384	0.041*
C3	0.5054 (5)	0.0318 (2)	0.7645 (3)	0.0361 (7)
H3	0.5112	−0.0382	0.7874	0.043*
C4	0.5811 (5)	0.1021 (2)	0.8818 (3)	0.0360 (7)
H4	0.6419	0.0790	0.9832	0.043*
C5	0.5688 (4)	0.2030 (2)	0.8526 (3)	0.0331 (7)
H5	0.6186	0.2492	0.9343	0.040*
C6	0.4826 (4)	0.2396 (2)	0.7019 (3)	0.0282 (6)
C7	0.4633 (4)	0.3437 (2)	0.6587 (3)	0.0280 (6)
C8	0.3796 (4)	0.3683 (2)	0.5077 (3)	0.0294 (6)
H8	0.3617	0.4370	0.4780	0.035*
C9	0.3195 (4)	0.2915 (2)	0.3955 (3)	0.0296 (6)
C10	0.2341 (4)	0.3167 (2)	0.2296 (3)	0.0318 (7)
C11	0.1402 (5)	0.4069 (2)	0.1854 (4)	0.0373 (7)
H11	0.1363	0.4552	0.2616	0.045*
C12	0.0520 (5)	0.4267 (3)	0.0301 (4)	0.0460 (8)
H12	−0.0135	0.4877	0.0007	0.055*
C13	0.0603 (5)	0.3570 (3)	−0.0810 (4)	0.0479 (9)
H13	−0.0009	0.3698	−0.1868	0.058*
C14	0.1574 (6)	0.2689 (3)	−0.0383 (4)	0.0477 (9)
H14	0.1659	0.2224	−0.1155	0.057*
C15	0.2429 (5)	0.2475 (3)	0.1164 (4)	0.0400 (8)
H15	0.3071	0.1859	0.1449	0.048*
C16	0.5387 (4)	0.4248 (2)	0.7759 (3)	0.0278 (6)
C17	0.7413 (4)	0.6576 (2)	0.7606 (3)	0.0293 (6)
H17	0.7424	0.6530	0.6563	0.035*
C18	0.8117 (4)	0.7491 (2)	0.8492 (3)	0.0278 (6)
C19	0.8098 (5)	0.7608 (2)	1.0015 (3)	0.0349 (7)
H19	0.7640	0.7083	1.0510	0.042*
C20	0.8744 (5)	0.8485 (2)	1.0807 (4)	0.0381 (7)
H20	0.8715	0.8565	1.1841	0.046*
C21	0.9431 (5)	0.9247 (2)	1.0102 (4)	0.0381 (7)
H21	0.9869	0.9850	1.0653	0.046*
C22	0.9483 (5)	0.9136 (2)	0.8603 (4)	0.0371 (7)
H22	0.9976	0.9655	0.8125	0.044*
C23	0.8806 (4)	0.8257 (2)	0.7794 (3)	0.0328 (7)
H23	0.8818	0.8184	0.6755	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0532 (14)	0.0323 (11)	0.0202 (10)	0.0008 (10)	0.0114 (9)	−0.0002 (8)
N1	0.0352 (15)	0.0334 (13)	0.0238 (12)	−0.0015 (11)	0.0065 (10)	0.0007 (10)
N2	0.0400 (15)	0.0293 (12)	0.0177 (10)	−0.0012 (10)	0.0058 (9)	−0.0007 (9)
N3	0.0354 (15)	0.0285 (12)	0.0223 (11)	−0.0006 (10)	0.0044 (10)	−0.0023 (9)
C1	0.0334 (16)	0.0288 (14)	0.0237 (13)	0.0004 (12)	0.0070 (11)	−0.0004 (11)
C2	0.0410 (19)	0.0311 (15)	0.0302 (16)	−0.0017 (14)	0.0093 (14)	−0.0037 (12)
C3	0.045 (2)	0.0270 (15)	0.0353 (16)	0.0014 (13)	0.0107 (14)	0.0043 (12)
C4	0.047 (2)	0.0327 (16)	0.0254 (15)	0.0025 (14)	0.0064 (13)	0.0031 (11)
C5	0.0429 (19)	0.0321 (15)	0.0218 (14)	0.0003 (13)	0.0058 (13)	0.0000 (12)
C6	0.0323 (17)	0.0297 (15)	0.0222 (13)	0.0016 (12)	0.0076 (11)	0.0011 (11)
C7	0.0326 (17)	0.0275 (14)	0.0233 (13)	0.0008 (12)	0.0075 (11)	−0.0006 (11)
C8	0.0361 (17)	0.0291 (14)	0.0213 (13)	0.0004 (12)	0.0057 (11)	0.0015 (11)
C9	0.0308 (17)	0.0338 (15)	0.0229 (13)	−0.0011 (13)	0.0059 (12)	−0.0002 (11)
C10	0.0309 (17)	0.0399 (17)	0.0219 (14)	−0.0039 (13)	0.0038 (12)	0.0002 (12)
C11	0.0402 (19)	0.0422 (17)	0.0254 (15)	0.0001 (14)	0.0034 (12)	0.0025 (13)
C12	0.044 (2)	0.052 (2)	0.0355 (18)	0.0004 (16)	0.0009 (14)	0.0093 (15)
C13	0.049 (2)	0.065 (2)	0.0227 (16)	−0.0093 (18)	0.0005 (14)	0.0049 (15)
C14	0.054 (2)	0.061 (2)	0.0237 (15)	−0.0054 (18)	0.0058 (14)	−0.0045 (15)
C15	0.046 (2)	0.0445 (18)	0.0262 (15)	−0.0002 (15)	0.0060 (13)	−0.0019 (13)
C16	0.0352 (17)	0.0272 (14)	0.0192 (14)	0.0029 (12)	0.0049 (11)	0.0004 (10)
C17	0.0337 (17)	0.0315 (15)	0.0214 (13)	0.0016 (12)	0.0060 (11)	0.0018 (11)
C18	0.0279 (16)	0.0308 (14)	0.0220 (13)	0.0019 (12)	0.0033 (11)	0.0000 (11)
C19	0.0392 (18)	0.0399 (17)	0.0260 (15)	−0.0053 (14)	0.0103 (13)	−0.0014 (12)
C20	0.043 (2)	0.0463 (18)	0.0248 (14)	−0.0055 (15)	0.0104 (13)	−0.0066 (13)
C21	0.0415 (19)	0.0350 (17)	0.0349 (17)	−0.0007 (14)	0.0068 (14)	−0.0077 (13)
C22	0.0451 (19)	0.0302 (15)	0.0341 (16)	−0.0011 (13)	0.0090 (13)	0.0016 (12)
C23	0.0398 (19)	0.0330 (15)	0.0236 (14)	0.0033 (13)	0.0065 (12)	0.0022 (11)

Geometric parameters (Å, º) top

O1—C16	1.231 (3)	C10—C15	1.395 (4)
N1—C9	1.324 (3)	C11—C12	1.394 (4)
N1—C1	1.367 (4)	C11—H11	0.9500
N2—C16	1.353 (4)	C12—C13	1.382 (5)
N2—N3	1.378 (3)	C12—H12	0.9500
N2—H2A	0.88 (4)	C13—C14	1.381 (5)
N3—C17	1.279 (4)	C13—H13	0.9500
C1—C2	1.416 (4)	C14—C15	1.390 (5)
C1—C6	1.418 (4)	C14—H14	0.9500
C2—C3	1.363 (4)	C15—H15	0.9500
C2—H2	0.9500	C17—C18	1.469 (4)
C3—C4	1.406 (4)	C17—H17	0.9500
C3—H3	0.9500	C18—C23	1.383 (4)
C4—C5	1.365 (4)	C18—C19	1.393 (4)
C4—H4	0.9500	C19—C20	1.382 (4)
C5—C6	1.416 (4)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.383 (5)
C6—C7	1.434 (4)	C20—H20	0.9500
C7—C8	1.367 (4)	C21—C22	1.379 (4)
C7—C16	1.504 (4)	C21—H21	0.9500
C8—C9	1.418 (4)	C22—C23	1.395 (4)
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.489 (4)	C23—H23	0.9500
C10—C11	1.395 (4)

C9—N1—C1	118.1 (2)	C10—C11—H11	119.8
C16—N2—N3	118.8 (2)	C13—C12—C11	119.7 (3)
C16—N2—H2A	121 (2)	C13—C12—H12	120.1
N3—N2—H2A	119 (2)	C11—C12—H12	120.1
C17—N3—N2	115.4 (2)	C14—C13—C12	120.1 (3)
N1—C1—C2	117.1 (2)	C14—C13—H13	120.0
N1—C1—C6	123.4 (2)	C12—C13—H13	120.0
C2—C1—C6	119.5 (3)	C13—C14—C15	120.7 (3)
C3—C2—C1	120.9 (3)	C13—C14—H14	119.7
C3—C2—H2	119.6	C15—C14—H14	119.7
C1—C2—H2	119.6	C14—C15—C10	119.7 (3)
C2—C3—C4	119.6 (3)	C14—C15—H15	120.1
C2—C3—H3	120.2	C10—C15—H15	120.1
C4—C3—H3	120.2	O1—C16—N2	123.2 (3)
C5—C4—C3	121.2 (3)	O1—C16—C7	122.0 (3)
C5—C4—H4	119.4	N2—C16—C7	114.9 (2)
C3—C4—H4	119.4	N3—C17—C18	121.7 (2)
C4—C5—C6	120.6 (3)	N3—C17—H17	119.1
C4—C5—H5	119.7	C18—C17—H17	119.1
C6—C5—H5	119.7	C23—C18—C19	119.2 (3)
C5—C6—C1	118.2 (2)	C23—C18—C17	119.2 (2)
C5—C6—C7	125.1 (3)	C19—C18—C17	121.6 (3)
C1—C6—C7	116.6 (2)	C20—C19—C18	120.1 (3)
C8—C7—C6	118.9 (3)	C20—C19—H19	120.0
C8—C7—C16	120.2 (3)	C18—C19—H19	120.0
C6—C7—C16	120.8 (3)	C19—C20—C21	120.4 (3)
C7—C8—C9	120.2 (3)	C19—C20—H20	119.8
C7—C8—H8	119.9	C21—C20—H20	119.8
C9—C8—H8	119.9	C22—C21—C20	120.2 (3)
N1—C9—C8	122.6 (3)	C22—C21—H21	119.9
N1—C9—C10	116.4 (2)	C20—C21—H21	119.9
C8—C9—C10	121.0 (3)	C21—C22—C23	119.5 (3)
C11—C10—C15	119.3 (3)	C21—C22—H22	120.2
C11—C10—C9	121.2 (3)	C23—C22—H22	120.2
C15—C10—C9	119.5 (3)	C18—C23—C22	120.6 (3)
C12—C11—C10	120.4 (3)	C18—C23—H23	119.7
C12—C11—H11	119.8	C22—C23—H23	119.7

C16—N2—N3—C17	−177.6 (3)	C8—C9—C10—C15	154.4 (3)
C9—N1—C1—C2	177.6 (3)	C15—C10—C11—C12	1.6 (5)
C9—N1—C1—C6	−2.9 (4)	C9—C10—C11—C12	−176.2 (3)
N1—C1—C2—C3	177.0 (3)	C10—C11—C12—C13	−1.0 (5)
C6—C1—C2—C3	−2.5 (5)	C11—C12—C13—C14	−0.8 (6)
C1—C2—C3—C4	−0.2 (5)	C12—C13—C14—C15	2.1 (6)
C2—C3—C4—C5	2.2 (5)	C13—C14—C15—C10	−1.5 (5)
C3—C4—C5—C6	−1.4 (5)	C11—C10—C15—C14	−0.4 (5)
C4—C5—C6—C1	−1.4 (4)	C9—C10—C15—C14	177.5 (3)
C4—C5—C6—C7	−179.6 (3)	N3—N2—C16—O1	−3.3 (4)
N1—C1—C6—C5	−176.2 (3)	N3—N2—C16—C7	177.0 (3)
C2—C1—C6—C5	3.3 (4)	C8—C7—C16—O1	144.0 (3)
N1—C1—C6—C7	2.2 (4)	C6—C7—C16—O1	−37.9 (4)
C2—C1—C6—C7	−178.3 (3)	C8—C7—C16—N2	−36.4 (4)
C5—C6—C7—C8	178.8 (3)	C6—C7—C16—N2	141.7 (3)
C1—C6—C7—C8	0.5 (4)	N2—N3—C17—C18	178.7 (3)
C5—C6—C7—C16	0.6 (4)	N3—C17—C18—C23	179.0 (3)
C1—C6—C7—C16	−177.6 (3)	N3—C17—C18—C19	−1.3 (5)
C6—C7—C8—C9	−2.4 (4)	C23—C18—C19—C20	0.7 (5)
C16—C7—C8—C9	175.8 (3)	C17—C18—C19—C20	−179.0 (3)
C1—N1—C9—C8	0.9 (4)	C18—C19—C20—C21	−0.7 (5)
C1—N1—C9—C10	−179.6 (3)	C19—C20—C21—C22	−0.2 (5)
C7—C8—C9—N1	1.8 (5)	C20—C21—C22—C23	1.2 (5)
C7—C8—C9—C10	−177.8 (3)	C19—C18—C23—C22	0.3 (5)
N1—C9—C10—C11	152.7 (3)	C17—C18—C23—C22	179.9 (3)
C8—C9—C10—C11	−27.8 (4)	C21—C22—C23—C18	−1.2 (5)
N1—C9—C10—C15	−25.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.95	2.34	2.939 (3)	121
N2—H2A···O1ⁱ	0.88 (4)	2.08 (4)	2.907 (3)	155 (4)
C8—H8···O1ⁱ	0.95	2.50	3.288 (3)	140
C17—H17···O1ⁱ	0.95	2.52	3.268 (3)	136

Symmetry code: (i) x, −y+1, z−1/2.

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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