5,6-Dimethyl-2-[(5-methyl-1,2-oxazol-3-yl)meth­yl]-1-(prop-2-en-1-yl)-1H-1,3-benzo­diazole

Benyahya, M.A.; El Azzaoui, B.; Sebbar, N.K.; Ouzidan, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617006472

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x170647

https://doi.org/10.1107/S2414314617006472

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5,6-Dimethyl-2-[(5-methyl-1,2-oxazol-3-yl)methyl]-1-(prop-2-en-1-yl)-1H-1,3-benzodiazole

Mohamed Ali Benyahya,^a ^* Brahim El Azzaoui,^a Nada Kheira Sebbar,^a Younes Ouzidan,^b El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: benyahyamohamedali2017@gmail.com

Edited by P. C. Healy, Griffith University, Australia (Received 27 April 2017; accepted 29 April 2017; online 13 July 2017)

In the title compound, C₁₇H₁₉N₃O, the benzodiazole moiety is twisted slightly end-to-end. In the crystal, two sets of weak C—H⋯N hydrogen bonds form sheets approximately parallel to (100), which are formed into bilayers by pairwise C—H⋯π(ring) interactions.

Keywords: crystal structure; benzodiazole; oxazole; hydrogen bonding; C—H⋯π(ring) interactions.

CCDC reference: 1547028

Structure description

Benzimidazole derivatives have been shown to possess various biological activities including anti-histaminic (Al Muhaimeed, 1997 ) anti-ulcerative (Scott et al., 2002 ) and anti-allergic (Nakano et al., 2000 ). In addition, they are effective against the human cytomegalovirus (HCMV) (Zhu et al., 2000 ) and are also efficient selective neuropeptide Y Y1 receptor antagonists (Zarrinmayeh et al., 1998 ). Isoxazole derivatives represent a unique class of nitrogen and oxygen-containing five-membered heterocycles and are the components of a variety of natural products and medicinally useful compounds (Sperry & Wright, 2005 ). Isoxazole derivatives with a variety of substituents are known to have various biological activities in both the pharmaceutical and agricultural areas (Lang & Lin, 1984 ; Boyd, 1991 ). As a continuation of our previous studies (Sebbar et al., 2015 , 2016 ; El Azzaoui et al., 2006 ), we were interested in the synthesis and the crystal structure of the title compound (Fig. 1).

Figure 1
The title molecule with the labeling scheme and 50% probability ellipsoids.

The benzodiazole moiety is slightly non-planar, as indicated by the dihedral angle of 1.3 (1)° between the five- and six-membered rings. The oxazole ring is planar to within 0.005 (1) Å and makes a dihedral angle of 89.78 (8)° with the diazole ring.

In the crystal, weak C2—H2⋯N1(x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z) hydrogen bonds link the molecules into chains running along the c-axis direction, which are joined into corrugated sheets by weak C12—H12⋯N3(x, −1 + y, z) hydrogen bonds running approximately parallel to the c-axis direction (Table 1 and Figs. 2 and 3). The sheets are formed into bilayers through complementary C14—H14A⋯π(ring) interactions across centers of symmetry (Table 1 and Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N3/O1/C11–C13 oxazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1ⁱ	1.010 (19)	2.65 (2)	3.603 (2)	157.9 (15)
C12—H12⋯N3ⁱⁱ	1.00 (2)	2.50 (3)	3.358 (3)	143.6 (17)
C14—H14A⋯Cg1ⁱⁱⁱ	1.01 (3)	2.77 (3)	3.704 (3)	154 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x+1, -y+2, -z.

Figure 2
Detail of the C—H⋯N hydrogen bonds (black dotted lines) and the C—H⋯π(ring) interactions (orange dotted lines). Symmetry codes: (i) x, −1 + y, z; (ii) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z; (iii) 1 − x, 2 − y, −z).

Figure 3
Packing viewed along the b axis (color code as in Fig. 2

Synthesis and crystallization

To a solution of 5,6-dimethyl-2-(5-methyl-isoxazol-3-yl)-methyl-1H-benzimidazole (4.3 mmol; 1.07 g) in N,N-dimethylformamide (20 ml) were added allyl bromide (4.5 mmol; 0.54 g), potassium carbonate (4.3 mmol) and a catalytic amount of tetra-n-butylammonium bromide. The reaction mixture was stirred at room temperature for 12 h. After cooling, the solid material was removed by filtration and the solvent evaporated in reduced pressure. The residue obtained was recrystallized from ethanol solution to afford the title compound as colourless crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O
M_r	281.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	19.6067 (6), 5.5438 (2), 14.0069 (5)
β (°)	99.911 (2)
V (Å³)	1499.77 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.63
Crystal size (mm)	0.12 × 0.07 × 0.01

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.86, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	10867, 2825, 2121
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.111, 1.05
No. of reflections	2825
No. of parameters	267
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23
Computer programs: APEX3 and SAINT (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1547028

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617006472/hg4022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006472/hg4022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617006472/hg4022Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617006472/hg4022Isup4.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: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5,6-Dimethyl-2-[(5-methyl-1,2-oxazol-3-yl)methyl]-1-(prop-2-en-1-yl)-1H-1,3-benzodiazole top

Crystal data top

C₁₇H₁₉N₃O	F(000) = 600
M_r = 281.35	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 19.6067 (6) Å	Cell parameters from 5620 reflections
b = 5.5438 (2) Å	θ = 4.6–70.0°
c = 14.0069 (5) Å	µ = 0.63 mm⁻¹
β = 99.911 (2)°	T = 150 K
V = 1499.77 (9) Å³	Plate, colourless
Z = 4	0.12 × 0.07 × 0.01 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2825 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2121 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
Detector resolution: 10.4167 pixels mm^-1	θ_max = 70.0°, θ_min = 2.3°
ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −6→6
T_min = 0.86, T_max = 0.99	l = −15→16
10867 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	All H-atom parameters refined
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0433P)² + 0.5009P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2825 reflections	Δρ_max = 0.20 e Å⁻³
267 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL 2014/7 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (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.

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

	x	y	z	U_iso*/U_eq
O1	0.54770 (7)	1.1344 (3)	0.13741 (12)	0.0466 (4)
N1	0.80943 (8)	0.7372 (3)	0.15996 (11)	0.0339 (4)
N2	0.77640 (7)	0.9145 (3)	0.28924 (11)	0.0303 (4)
N3	0.61491 (9)	1.2309 (3)	0.13994 (14)	0.0457 (5)
C1	0.82047 (8)	0.7281 (3)	0.32548 (13)	0.0264 (4)
C2	0.84425 (8)	0.6479 (3)	0.41974 (13)	0.0275 (4)
H2	0.8297 (9)	0.725 (3)	0.4785 (14)	0.031 (5)*
C3	0.89030 (8)	0.4559 (3)	0.43144 (13)	0.0277 (4)
C4	0.91251 (8)	0.3476 (3)	0.35005 (13)	0.0283 (4)
C5	0.88754 (9)	0.4304 (4)	0.25751 (14)	0.0309 (4)
H5	0.9042 (11)	0.356 (4)	0.1992 (15)	0.040 (6)*
C6	0.84092 (8)	0.6209 (3)	0.24493 (13)	0.0285 (4)
C7	0.77223 (9)	0.9087 (4)	0.19014 (14)	0.0325 (4)
C8	0.91514 (10)	0.3569 (4)	0.53132 (14)	0.0356 (5)
H8A	0.9678 (11)	0.351 (4)	0.5505 (14)	0.039 (6)*
H8B	0.8968 (12)	0.454 (4)	0.5818 (17)	0.050 (6)*
H8C	0.8988 (11)	0.181 (4)	0.5357 (16)	0.048 (6)*
C9	0.96358 (10)	0.1413 (4)	0.36417 (17)	0.0378 (5)
H9A	0.9451 (12)	0.007 (5)	0.4013 (18)	0.058 (7)*
H9B	1.0101 (13)	0.191 (4)	0.4038 (17)	0.058 (7)*
H9C	0.9742 (12)	0.087 (4)	0.2990 (19)	0.061 (7)*
C10	0.72902 (10)	1.0819 (4)	0.12321 (17)	0.0409 (5)
H10A	0.7409 (11)	1.256 (4)	0.1425 (15)	0.045 (6)*
H10B	0.7401 (11)	1.053 (4)	0.0554 (17)	0.046 (6)*
C11	0.65309 (10)	1.0480 (3)	0.12356 (14)	0.0343 (5)
C12	0.61480 (10)	0.8321 (4)	0.11048 (14)	0.0343 (4)
H12	0.6306 (12)	0.664 (5)	0.0994 (17)	0.056 (7)*
C13	0.55011 (10)	0.8941 (4)	0.12044 (14)	0.0348 (4)
C14	0.48476 (11)	0.7599 (5)	0.1177 (2)	0.0465 (6)
H14A	0.4485 (14)	0.812 (5)	0.061 (2)	0.076 (9)*
H14B	0.4933 (15)	0.583 (6)	0.108 (2)	0.087 (10)*
H14C	0.4654 (13)	0.782 (5)	0.175 (2)	0.068 (8)*
C15	0.74467 (10)	1.0827 (4)	0.34788 (16)	0.0368 (5)
H15A	0.7314 (11)	1.234 (4)	0.3106 (17)	0.052 (6)*
H15B	0.7805 (11)	1.135 (4)	0.4056 (16)	0.046 (6)*
C16	0.68341 (10)	0.9834 (4)	0.38483 (16)	0.0414 (5)
H16	0.6641 (12)	1.081 (4)	0.4300 (17)	0.054 (7)*
C17	0.65382 (11)	0.7744 (5)	0.36319 (17)	0.0461 (6)
H17A	0.6126 (14)	0.723 (5)	0.3939 (19)	0.073 (8)*
H17B	0.6715 (11)	0.663 (4)	0.3190 (16)	0.046 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0367 (8)	0.0343 (8)	0.0677 (11)	0.0044 (6)	0.0064 (7)	0.0012 (7)
N1	0.0293 (8)	0.0430 (10)	0.0289 (9)	−0.0025 (7)	0.0032 (6)	0.0063 (7)
N2	0.0256 (7)	0.0284 (8)	0.0364 (9)	0.0005 (6)	0.0039 (6)	0.0036 (7)
N3	0.0377 (9)	0.0312 (9)	0.0657 (13)	−0.0019 (8)	0.0017 (8)	0.0037 (8)
C1	0.0208 (8)	0.0276 (9)	0.0300 (10)	−0.0014 (7)	0.0028 (7)	0.0019 (7)
C2	0.0236 (8)	0.0304 (10)	0.0287 (10)	−0.0034 (7)	0.0050 (7)	−0.0015 (8)
C3	0.0234 (8)	0.0324 (10)	0.0269 (10)	−0.0032 (7)	0.0030 (7)	0.0022 (7)
C4	0.0220 (8)	0.0302 (10)	0.0331 (10)	−0.0002 (7)	0.0056 (7)	−0.0012 (7)
C5	0.0272 (9)	0.0369 (11)	0.0297 (10)	−0.0013 (8)	0.0077 (7)	−0.0039 (8)
C6	0.0243 (8)	0.0357 (10)	0.0256 (9)	−0.0035 (8)	0.0046 (7)	0.0014 (8)
C7	0.0251 (8)	0.0374 (11)	0.0337 (11)	−0.0057 (8)	0.0013 (7)	0.0089 (8)
C8	0.0353 (10)	0.0403 (12)	0.0296 (11)	0.0023 (9)	0.0013 (8)	0.0044 (9)
C9	0.0307 (10)	0.0378 (12)	0.0445 (13)	0.0066 (9)	0.0053 (9)	−0.0009 (10)
C10	0.0320 (10)	0.0411 (13)	0.0471 (13)	−0.0024 (9)	−0.0001 (9)	0.0152 (10)
C11	0.0336 (9)	0.0298 (10)	0.0369 (11)	0.0020 (8)	−0.0013 (8)	0.0087 (8)
C12	0.0344 (10)	0.0294 (10)	0.0371 (11)	0.0008 (8)	0.0008 (8)	0.0028 (8)
C13	0.0345 (10)	0.0319 (11)	0.0361 (11)	−0.0004 (8)	0.0006 (8)	0.0039 (8)
C14	0.0336 (11)	0.0496 (15)	0.0549 (15)	−0.0051 (10)	0.0032 (10)	0.0080 (11)
C15	0.0316 (10)	0.0303 (11)	0.0468 (13)	0.0047 (8)	0.0022 (9)	−0.0039 (9)
C16	0.0305 (10)	0.0473 (13)	0.0460 (13)	0.0062 (10)	0.0053 (9)	−0.0081 (10)
C17	0.0355 (11)	0.0545 (15)	0.0496 (14)	−0.0031 (11)	0.0109 (10)	0.0001 (11)

Geometric parameters (Å, º) top

O1—C13	1.356 (2)	C8—H8C	1.03 (2)
O1—N3	1.417 (2)	C9—H9A	1.01 (3)
N1—C7	1.312 (3)	C9—H9B	1.02 (3)
N1—C6	1.400 (2)	C9—H9C	1.02 (3)
N2—C7	1.377 (2)	C10—C11	1.501 (3)
N2—C1	1.386 (2)	C10—H10A	1.02 (2)
N2—C15	1.451 (2)	C10—H10B	1.02 (2)
N3—C11	1.304 (3)	C11—C12	1.408 (3)
C1—C6	1.394 (2)	C12—C13	1.344 (3)
C1—C2	1.395 (2)	C12—H12	1.00 (2)
C2—C3	1.387 (3)	C13—C14	1.476 (3)
C2—H2	1.010 (19)	C14—H14A	1.01 (3)
C3—C4	1.421 (2)	C14—H14B	1.01 (3)
C3—C8	1.504 (3)	C14—H14C	0.95 (3)
C4—C5	1.383 (3)	C15—C16	1.492 (3)
C4—C9	1.510 (3)	C15—H15A	1.00 (2)
C5—C6	1.388 (3)	C15—H15B	1.02 (2)
C5—H5	1.02 (2)	C16—C17	1.308 (3)
C7—C10	1.498 (3)	C16—H16	0.96 (2)
C8—H8A	1.02 (2)	C17—H17A	1.02 (3)
C8—H8B	1.00 (2)	C17—H17B	0.98 (2)

C13—O1—N3	108.37 (15)	C4—C9—H9C	109.9 (14)
C7—N1—C6	104.36 (15)	H9A—C9—H9C	113.1 (19)
C7—N2—C1	106.09 (15)	H9B—C9—H9C	105.5 (19)
C7—N2—C15	128.95 (16)	C7—C10—C11	111.83 (16)
C1—N2—C15	124.92 (16)	C7—C10—H10A	111.3 (12)
C11—N3—O1	105.15 (15)	C11—C10—H10A	107.5 (12)
N2—C1—C6	105.63 (15)	C7—C10—H10B	107.1 (12)
N2—C1—C2	132.06 (16)	C11—C10—H10B	110.7 (12)
C6—C1—C2	122.31 (16)	H10A—C10—H10B	108.5 (16)
C3—C2—C1	117.44 (16)	N3—C11—C12	112.00 (17)
C3—C2—H2	119.7 (11)	N3—C11—C10	120.16 (18)
C1—C2—H2	122.9 (11)	C12—C11—C10	127.81 (19)
C2—C3—C4	120.83 (16)	C13—C12—C11	105.13 (18)
C2—C3—C8	119.33 (17)	C13—C12—H12	125.1 (13)
C4—C3—C8	119.82 (17)	C11—C12—H12	129.7 (13)
C5—C4—C3	120.25 (16)	C12—C13—O1	109.34 (17)
C5—C4—C9	119.59 (17)	C12—C13—C14	134.3 (2)
C3—C4—C9	120.16 (17)	O1—C13—C14	116.33 (19)
C4—C5—C6	119.38 (17)	C13—C14—H14A	111.4 (15)
C4—C5—H5	120.4 (12)	C13—C14—H14B	109.3 (17)
C6—C5—H5	120.2 (12)	H14A—C14—H14B	107 (2)
C5—C6—C1	119.77 (16)	C13—C14—H14C	112.5 (16)
C5—C6—N1	129.98 (17)	H14A—C14—H14C	107 (2)
C1—C6—N1	110.23 (16)	H14B—C14—H14C	110 (2)
N1—C7—N2	113.69 (16)	N2—C15—C16	114.11 (17)
N1—C7—C10	123.28 (19)	N2—C15—H15A	110.0 (13)
N2—C7—C10	123.02 (19)	C16—C15—H15A	109.7 (13)
C3—C8—H8A	114.1 (12)	N2—C15—H15B	109.1 (12)
C3—C8—H8B	111.2 (13)	C16—C15—H15B	108.4 (12)
H8A—C8—H8B	107.5 (17)	H15A—C15—H15B	105.1 (18)
C3—C8—H8C	110.3 (12)	C17—C16—C15	126.7 (2)
H8A—C8—H8C	105.3 (17)	C17—C16—H16	116.4 (14)
H8B—C8—H8C	108.2 (17)	C15—C16—H16	116.9 (14)
C4—C9—H9A	109.7 (14)	C16—C17—H17A	120.1 (16)
C4—C9—H9B	112.0 (14)	C16—C17—H17B	121.0 (13)
H9A—C9—H9B	106.6 (19)	H17A—C17—H17B	119 (2)

C13—O1—N3—C11	0.7 (2)	C7—N1—C6—C1	0.6 (2)
C7—N2—C1—C6	0.45 (18)	C6—N1—C7—N2	−0.3 (2)
C15—N2—C1—C6	−177.34 (16)	C6—N1—C7—C10	179.90 (17)
C7—N2—C1—C2	179.60 (18)	C1—N2—C7—N1	−0.1 (2)
C15—N2—C1—C2	1.8 (3)	C15—N2—C7—N1	177.57 (17)
N2—C1—C2—C3	−178.43 (17)	C1—N2—C7—C10	179.71 (16)
C6—C1—C2—C3	0.6 (3)	C15—N2—C7—C10	−2.6 (3)
C1—C2—C3—C4	0.5 (2)	N1—C7—C10—C11	113.8 (2)
C1—C2—C3—C8	−177.59 (16)	N2—C7—C10—C11	−66.0 (3)
C2—C3—C4—C5	−1.0 (3)	O1—N3—C11—C12	−0.3 (2)
C8—C3—C4—C5	177.09 (17)	O1—N3—C11—C10	−178.57 (17)
C2—C3—C4—C9	178.99 (17)	C7—C10—C11—N3	126.8 (2)
C8—C3—C4—C9	−2.9 (3)	C7—C10—C11—C12	−51.2 (3)
C3—C4—C5—C6	0.3 (3)	N3—C11—C12—C13	−0.3 (2)
C9—C4—C5—C6	−179.63 (17)	C10—C11—C12—C13	177.8 (2)
C4—C5—C6—C1	0.7 (3)	C11—C12—C13—O1	0.8 (2)
C4—C5—C6—N1	179.09 (17)	C11—C12—C13—C14	−178.6 (2)
N2—C1—C6—C5	178.01 (15)	N3—O1—C13—C12	−1.0 (2)
C2—C1—C6—C5	−1.2 (3)	N3—O1—C13—C14	178.53 (18)
N2—C1—C6—N1	−0.65 (19)	C7—N2—C15—C16	104.1 (2)
C2—C1—C6—N1	−179.90 (16)	C1—N2—C15—C16	−78.7 (2)
C7—N1—C6—C5	−177.89 (19)	N2—C15—C16—C17	−5.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N3/O1/C11–C13 oxazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1ⁱ	1.010 (19)	2.65 (2)	3.603 (2)	157.9 (15)
C12—H12···N3ⁱⁱ	1.00 (2)	2.50 (3)	3.358 (3)	143.6 (17)
C14—H14A···Cg1ⁱⁱⁱ	1.01 (3)	2.77 (3)	3.704 (3)	154 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+2, −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.

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