2-(4-Chloro-2-nitro­phen­yl)-5-[4-(prop­yloxy)phen­yl]-1,3,4-oxa­diazole

Limbach, D.; Detert, H.; Schollmeyer, D.

doi:10.1107/S241431461601782X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161782

https://doi.org/10.1107/S241431461601782X

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2-(4-Chloro-2-nitrophenyl)-5-[4-(propyloxy)phenyl]-1,3,4-oxadiazole

Daniel Limbach,^a Heiner Detert ^a ^* and Dieter Schollmeyer ^a

^aUniversity of Mainz, Institut for Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: detert@uni-mainz.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 November 2016; accepted 7 November 2016; online 10 November 2016)

The title compound, C₁₇H₁₄ClN₃O₄, was prepared by the Huisgen reaction of 4-chloro-2-nitrobenzoyl chloride and 5-(4-propyloxyphenyl)tetrazole. The diphenyl-1,3,4-oxadiazole unit is nearly planar. The oxadiazole ring is inclined to the 4-chloro-2-nitrophenyl ring by 7.77 (8)°, and by 7.93 (8)° to the 4-propyloxyphenyl ring. The benzene rings are inclined to one another by 1.32 (7)°. The nitro group is twisted out of the plane of the benzene ring to which it is attached by 73.59 (16)°. The propoxy chain mean plane is inclined to the benzene ring to which it is attached by 4.46 (13)°. In the crystal, C—H⋯O and C—H⋯N hydrogen bonds connect the molecules, forming ribbons propagating along the b-axis direction. The ribbons are linked by C—H⋯π interactions, forming slabs parallel to the ab plane.

Keywords: crystal structure; 1,3,4-oxadiazole; nitro compound; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1515447

Structure description

Donor–acceptor substituted π-systems are solvatochromic (Detert et al. 2002 ; Rettig 1986 ), making these materials interesting for sensing and non-linear optical applications (Schmitt et al. 2008 ; Schönhaber et al. 2010 ; Franco et al. 2010 ). o-Nitrobiaryl compounds are starting materials for the Cadogan cyclization (Cadogan 1962 ; Letessier et al. 2013 ).

Apart from the nitro group, te title compound, Fig. 1, is nearly planar. The oxadiazole ring (O8/N10/N11/C7/C9) is inclined to the benzene ring (C1–C6) by 7.77 (8)° and by 7.93 (8)° to benzene ring (C12–C17). The benzene rings are inclined to one another by 1.32 (7)°. The nitro group is twisted out of the plane of the benzene ring (C1–C6), to which it is attached, by 73.59 (16)%. The propoxy chain mean plane (O18/C19–C21) is inclined to the benzene ring (C12–C17), to which it is attached, by 4.46 (13)°. The torsion angles along the biaryl axes are −7.5 (2)° (C6—C1—C7—N11) and 7.7 (2)° (N10—C9—C12—C17). The bonds connecting the central 1,3,4-oxadiazole ring with the donor- and acceptor-substituted benzene rings, 1.4555 (17) and 1.4527 (17) Å, respectively, are very similar. The C4—Cl1 bond length of 1.7270 (14) Å is nearly identical to the bond lengths [1.727, 1.728 Å] found in 1-chloro-3,4-dinitrobenzene (Wilkins & Small, 1985 ).

Figure 1
A view of the molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the crystal, molecules are connected via C—H⋯O and C—H⋯N hydrogen bonds, involving the aromatic rings to the the nitro and oxadiazole groups, respectively, forming ribbons that propagate along the b-axis direction (Table 1 and Fig. 2). The ribbons are linked by C—H⋯π interactions, forming slabs parallel to the ab plane (Table 1 and Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of ring C12–C17.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O24ⁱ	0.95	2.57	3.4821 (18)	161
C14—H14⋯N10ⁱ	0.95	2.41	3.3351 (19)	163
C20—H20B⋯Cgⁱⁱ	0.99	2.86	3.7524 (17)	151
C21—H21B⋯Cgⁱⁱⁱ	0.99	2.84	3.6473 (17)	140
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) -x, -y, -z.

Figure 2
A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1

), and H atoms not involved in these interactions have been excluded.

Figure 3
A partial view along the b axis of the crystal packing of the title compound. The C—H⋯π interactions are illustrated as dashed lines (see Table 1

), and H atoms not involved in the intermolecular interactions have been excluded.

Synthesis and crystallization

4-Chloro-2-nitrobenzoic acid (640 mg, 3.18 mmol) was refluxed for 12 h in thionyl chloride (6 ml, 82.7 mmol), excess thionyl chloride was distilled off in vacuo and the crude benzoyl chloride was dissolved in toluene (15 ml), then 5-(4-propyloxyphenyl)tetrazole (466 mg, 2.28 mmol) and 2,4,6-collidine (0.6 ml, 4.53 mmol) were added. After refluxing for 72 h, the mixture was cooled and 2N HCl_(aq) (25 ml) was added. The aqueous phase was extracted with chloroform (3 × 20 ml). The combined organic phase was dried with MgSO₄ followed by evaporation and column chromatography (silica gel, toluene: ethyl acetate = 40:1) to afforded 723 mg of the title compound (yield 88%). ¹H NMR (CDCl₃) δ 8.07 (d, J = 8.4 Hz, 1H), 7.98–7.95 (m, 3H), 7.75 (dd, J = 8.4, 2.1 Hz, 1H), 7.02 – 6.99 (m, 2H), 4.00 (t, J = 6.5 Hz, 2H), 1.89–1.80 (m, 2H), 1.06 (t, J = 7.4 Hz, 3H). ¹³C NMR (CDCl₃) δ 166.1, 162.6, 160.0, 138.6, 133.2, 132.5, 129.1, 125.0, 117.1, 115.4, 115.3, 8.16, 69.9, 22.6, 10.6. The title compound was crystallized from a dichloromethane solution giving colourless plate-like crystals (m.p. 419–411 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClN₃O₄
M_r	359.76
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	193
a, b, c (Å)	7.5691 (5), 7.7907 (5), 14.904 (1)
α, β, γ (°)	101.911 (5), 91.311 (5), 107.224 (5)
V (Å³)	818.06 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.26
Crystal size (mm)	0.44 × 0.28 × 0.08

Data collection
Diffractometer	STOE IPDS 2T
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7659, 3942, 3221
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.04
No. of reflections	3942
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.38
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 1996 ), SHELXT2014 (Sheldrick, 2015a ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2008 ) and SHELXL2014 (Sheldrick, 2015b ).

Structural data

CCDC reference: 1515447

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431461601782X/su4093sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461601782X/su4093Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461601782X/su4093Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 1996); cell refinement: X-AREA (Stoe & Cie, 1996); data reduction: X-RED32 (Stoe & Cie, 1996); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009).

2-(4-Chloro-2-nitrophenyl)-5-[4-(propyloxy)phenyl]-1,3,4-oxadiazole top

Crystal data top

C₁₇H₁₄ClN₃O₄	Z = 2
M_r = 359.76	F(000) = 372
Triclinic, P1	D_x = 1.461 Mg m⁻³
a = 7.5691 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7907 (5) Å	Cell parameters from 8906 reflections
c = 14.904 (1) Å	θ = 2.8–28.2°
α = 101.911 (5)°	µ = 0.26 mm⁻¹
β = 91.311 (5)°	T = 193 K
γ = 107.224 (5)°	Plate, colourless
V = 818.06 (10) Å³	0.44 × 0.28 × 0.08 mm

Data collection top

STOE IPDS 2T diffractometer	R_int = 0.018
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.1°, θ_min = 2.8°
rotation method scans	h = −8→10
7659 measured reflections	k = −10→10
3942 independent reflections	l = −19→19
3221 reflections with I > 2σ(I)

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0509P)² + 0.2041P] where P = (F_o² + 2F_c²)/3
3942 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.38 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.99714 (6)	1.19481 (5)	0.78094 (3)	0.04350 (12)
C1	0.74265 (17)	0.98285 (17)	0.48656 (9)	0.0236 (2)
C2	0.76872 (19)	0.86300 (17)	0.53984 (9)	0.0266 (3)
H2	0.7314	0.7343	0.5137	0.032*
C3	0.84763 (19)	0.92731 (19)	0.62969 (9)	0.0290 (3)
H3	0.8658	0.8438	0.6646	0.035*
C4	0.90006 (19)	1.11479 (19)	0.66840 (9)	0.0284 (3)
C5	0.87652 (19)	1.23889 (18)	0.61822 (9)	0.0293 (3)
H5	0.9124	1.3673	0.6449	0.035*
C6	0.79957 (18)	1.17076 (17)	0.52846 (9)	0.0251 (3)
C7	0.65423 (18)	0.91012 (17)	0.39304 (9)	0.0244 (3)
O8	0.61819 (13)	0.72641 (12)	0.35657 (6)	0.0254 (2)
C9	0.53202 (18)	0.70529 (17)	0.27188 (9)	0.0247 (3)
N10	0.51751 (18)	0.85882 (16)	0.25766 (8)	0.0330 (3)
N11	0.59744 (18)	0.99363 (16)	0.33768 (8)	0.0328 (3)
C12	0.46798 (18)	0.52310 (17)	0.21119 (9)	0.0249 (3)
C13	0.47390 (18)	0.36665 (18)	0.24229 (9)	0.0261 (3)
H13	0.5218	0.3791	0.3036	0.031*
C14	0.41008 (19)	0.19464 (18)	0.18386 (9)	0.0272 (3)
H14	0.4129	0.0887	0.2053	0.033*
C15	0.34137 (19)	0.17554 (18)	0.09339 (9)	0.0264 (3)
C16	0.33658 (19)	0.33078 (18)	0.06153 (9)	0.0281 (3)
H16	0.2917	0.3185	−0.0003	0.034*
C17	0.39800 (19)	0.50300 (18)	0.12099 (9)	0.0284 (3)
H17	0.3923	0.6086	0.1000	0.034*
O18	0.28345 (15)	0.00031 (13)	0.04241 (7)	0.0329 (2)
C19	0.2206 (2)	−0.03094 (19)	−0.05283 (9)	0.0302 (3)
H19A	0.3227	0.0304	−0.0868	0.036*
H19B	0.1163	0.0193	−0.0590	0.036*
C20	0.1582 (2)	−0.23635 (19)	−0.09084 (10)	0.0306 (3)
H20A	0.0605	−0.2966	−0.0544	0.037*
H20B	0.2643	−0.2845	−0.0855	0.037*
C21	0.0825 (2)	−0.2826 (2)	−0.19156 (10)	0.0399 (4)
H21A	0.1759	−0.2153	−0.2267	0.060*
H21B	−0.0304	−0.2466	−0.1961	0.060*
H21C	0.0534	−0.4154	−0.2166	0.060*
N22	0.78583 (16)	1.30994 (15)	0.47701 (8)	0.0285 (2)
O23	0.89671 (16)	1.34446 (14)	0.42036 (7)	0.0382 (3)
O24	0.66822 (17)	1.38593 (16)	0.49721 (9)	0.0472 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0577 (3)	0.0393 (2)	0.02601 (18)	0.00562 (17)	−0.01008 (15)	0.00578 (14)
C1	0.0236 (6)	0.0223 (6)	0.0239 (6)	0.0054 (5)	0.0023 (5)	0.0054 (5)
C2	0.0300 (6)	0.0216 (6)	0.0277 (6)	0.0069 (5)	0.0025 (5)	0.0059 (5)
C3	0.0327 (7)	0.0289 (6)	0.0271 (6)	0.0090 (5)	0.0029 (5)	0.0110 (5)
C4	0.0314 (7)	0.0295 (7)	0.0212 (6)	0.0056 (5)	−0.0001 (5)	0.0044 (5)
C5	0.0342 (7)	0.0227 (6)	0.0264 (6)	0.0036 (5)	0.0006 (5)	0.0035 (5)
C6	0.0267 (6)	0.0220 (6)	0.0259 (6)	0.0052 (5)	0.0026 (5)	0.0075 (5)
C7	0.0256 (6)	0.0196 (5)	0.0264 (6)	0.0052 (5)	0.0022 (5)	0.0044 (5)
O8	0.0323 (5)	0.0207 (4)	0.0219 (4)	0.0071 (3)	−0.0015 (4)	0.0037 (3)
C9	0.0257 (6)	0.0259 (6)	0.0216 (6)	0.0065 (5)	−0.0009 (5)	0.0059 (5)
N10	0.0424 (7)	0.0242 (5)	0.0299 (6)	0.0090 (5)	−0.0093 (5)	0.0036 (4)
N11	0.0410 (7)	0.0243 (5)	0.0306 (6)	0.0086 (5)	−0.0076 (5)	0.0037 (5)
C12	0.0261 (6)	0.0241 (6)	0.0231 (6)	0.0060 (5)	0.0007 (5)	0.0051 (5)
C13	0.0303 (6)	0.0272 (6)	0.0206 (6)	0.0086 (5)	−0.0024 (5)	0.0055 (5)
C14	0.0327 (7)	0.0251 (6)	0.0247 (6)	0.0096 (5)	−0.0004 (5)	0.0069 (5)
C15	0.0281 (6)	0.0264 (6)	0.0228 (6)	0.0073 (5)	0.0009 (5)	0.0034 (5)
C16	0.0324 (7)	0.0309 (7)	0.0196 (6)	0.0073 (5)	−0.0020 (5)	0.0068 (5)
C17	0.0331 (7)	0.0266 (6)	0.0256 (6)	0.0070 (5)	−0.0003 (5)	0.0097 (5)
O18	0.0459 (6)	0.0260 (5)	0.0229 (5)	0.0082 (4)	−0.0053 (4)	0.0018 (4)
C19	0.0355 (7)	0.0306 (7)	0.0218 (6)	0.0083 (5)	−0.0010 (5)	0.0028 (5)
C20	0.0320 (7)	0.0288 (6)	0.0268 (6)	0.0065 (5)	−0.0024 (5)	0.0018 (5)
C21	0.0479 (9)	0.0358 (8)	0.0290 (7)	0.0100 (7)	−0.0071 (6)	−0.0029 (6)
N22	0.0340 (6)	0.0206 (5)	0.0279 (6)	0.0041 (4)	−0.0025 (5)	0.0056 (4)
O23	0.0511 (6)	0.0310 (5)	0.0313 (5)	0.0067 (5)	0.0074 (5)	0.0125 (4)
O24	0.0483 (7)	0.0397 (6)	0.0648 (8)	0.0234 (5)	0.0108 (6)	0.0214 (6)

Geometric parameters (Å, º) top

Cl1—C4	1.7270 (14)	C13—H13	0.9500
C1—C2	1.3961 (18)	C14—C15	1.3964 (18)
C1—C6	1.3984 (17)	C14—H14	0.9500
C1—C7	1.4555 (17)	C15—O18	1.3548 (16)
C2—C3	1.3822 (19)	C15—C16	1.3970 (19)
C2—H2	0.9500	C16—C17	1.3867 (18)
C3—C4	1.3864 (19)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.3857 (19)	O18—C19	1.4346 (16)
C5—C6	1.3779 (18)	C19—C20	1.5069 (18)
C5—H5	0.9500	C19—H19A	0.9900
C6—N22	1.4768 (16)	C19—H19B	0.9900
C7—N11	1.2883 (17)	C20—C21	1.5253 (19)
C7—O8	1.3635 (14)	C20—H20A	0.9900
O8—C9	1.3633 (15)	C20—H20B	0.9900
C9—N10	1.2920 (17)	C21—H21A	0.9800
C9—C12	1.4527 (17)	C21—H21B	0.9800
N10—N11	1.4019 (16)	C21—H21C	0.9800
C12—C17	1.3941 (18)	N22—O23	1.2173 (16)
C12—C13	1.4026 (17)	N22—O24	1.2183 (17)
C13—C14	1.3796 (18)

C2—C1—C6	116.88 (12)	C13—C14—H14	119.8
C2—C1—C7	120.09 (11)	C15—C14—H14	119.8
C6—C1—C7	123.00 (11)	O18—C15—C14	115.03 (12)
C3—C2—C1	121.50 (12)	O18—C15—C16	124.85 (12)
C3—C2—H2	119.2	C14—C15—C16	120.13 (12)
C1—C2—H2	119.2	C17—C16—C15	119.33 (12)
C2—C3—C4	119.40 (12)	C17—C16—H16	120.3
C2—C3—H3	120.3	C15—C16—H16	120.3
C4—C3—H3	120.3	C16—C17—C12	120.80 (12)
C5—C4—C3	121.12 (12)	C16—C17—H17	119.6
C5—C4—Cl1	119.52 (10)	C12—C17—H17	119.6
C3—C4—Cl1	119.36 (11)	C15—O18—C19	118.75 (11)
C6—C5—C4	118.10 (12)	O18—C19—C20	107.23 (11)
C6—C5—H5	120.9	O18—C19—H19A	110.3
C4—C5—H5	120.9	C20—C19—H19A	110.3
C5—C6—C1	122.98 (12)	O18—C19—H19B	110.3
C5—C6—N22	115.73 (11)	C20—C19—H19B	110.3
C1—C6—N22	121.25 (11)	H19A—C19—H19B	108.5
N11—C7—O8	112.64 (11)	C19—C20—C21	110.74 (12)
N11—C7—C1	129.40 (12)	C19—C20—H20A	109.5
O8—C7—C1	117.93 (11)	C21—C20—H20A	109.5
C9—O8—C7	102.51 (10)	C19—C20—H20B	109.5
N10—C9—O8	112.22 (11)	C21—C20—H20B	109.5
N10—C9—C12	128.58 (12)	H20A—C20—H20B	108.1
O8—C9—C12	119.19 (11)	C20—C21—H21A	109.5
C9—N10—N11	106.49 (11)	C20—C21—H21B	109.5
C7—N11—N10	106.13 (11)	H21A—C21—H21B	109.5
C17—C12—C13	119.45 (12)	C20—C21—H21C	109.5
C17—C12—C9	119.63 (12)	H21A—C21—H21C	109.5
C13—C12—C9	120.92 (11)	H21B—C21—H21C	109.5
C14—C13—C12	119.97 (12)	O23—N22—O24	125.20 (12)
C14—C13—H13	120.0	O23—N22—C6	117.67 (11)
C12—C13—H13	120.0	O24—N22—C6	117.08 (12)
C13—C14—C15	120.31 (12)

C6—C1—C2—C3	−0.19 (19)	C1—C7—N11—N10	−178.06 (13)
C7—C1—C2—C3	−178.23 (13)	C9—N10—N11—C7	0.37 (16)
C1—C2—C3—C4	0.8 (2)	N10—C9—C12—C17	7.7 (2)
C2—C3—C4—C5	−0.7 (2)	O8—C9—C12—C17	−173.09 (12)
C2—C3—C4—Cl1	179.54 (11)	N10—C9—C12—C13	−171.67 (14)
C3—C4—C5—C6	−0.1 (2)	O8—C9—C12—C13	7.51 (19)
Cl1—C4—C5—C6	179.66 (11)	C17—C12—C13—C14	−0.3 (2)
C4—C5—C6—C1	0.8 (2)	C9—C12—C13—C14	179.14 (12)
C4—C5—C6—N22	−177.27 (12)	C12—C13—C14—C15	0.7 (2)
C2—C1—C6—C5	−0.6 (2)	C13—C14—C15—O18	179.73 (12)
C7—C1—C6—C5	177.33 (13)	C13—C14—C15—C16	−0.1 (2)
C2—C1—C6—N22	177.30 (12)	O18—C15—C16—C17	179.22 (13)
C7—C1—C6—N22	−4.7 (2)	C14—C15—C16—C17	−1.0 (2)
C2—C1—C7—N11	170.45 (14)	C15—C16—C17—C12	1.4 (2)
C6—C1—C7—N11	−7.5 (2)	C13—C12—C17—C16	−0.8 (2)
C2—C1—C7—O8	−7.31 (18)	C9—C12—C17—C16	179.77 (13)
C6—C1—C7—O8	174.78 (11)	C14—C15—O18—C19	−176.50 (12)
N11—C7—O8—C9	−0.04 (15)	C16—C15—O18—C19	3.3 (2)
C1—C7—O8—C9	178.09 (11)	C15—O18—C19—C20	−177.75 (12)
C7—O8—C9—N10	0.30 (15)	O18—C19—C20—C21	178.03 (12)
C7—O8—C9—C12	−179.01 (11)	C5—C6—N22—O23	104.46 (14)
O8—C9—N10—N11	−0.42 (16)	C1—C6—N22—O23	−73.63 (16)
C12—C9—N10—N11	178.80 (13)	C5—C6—N22—O24	−72.95 (16)
O8—C7—N11—N10	−0.20 (16)	C1—C6—N22—O24	108.97 (15)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of ring C12–C17.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O24ⁱ	0.95	2.57	3.4821 (18)	161
C14—H14···N10ⁱ	0.95	2.41	3.3351 (19)	163
C20—H20B···Cgⁱⁱ	0.99	2.86	3.7524 (17)	151
C21—H21B···Cgⁱⁱⁱ	0.99	2.84	3.6473 (17)	140

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

References

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Volume 1| Part 11| November 2016| x161782

https://doi.org/10.1107/S241431461601782X

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

2-(4-Chloro-2-nitro­phen­yl)-5-[4-(prop­yl­oxy)phen­yl]-1,3,4-oxa­diazole

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

2-(4-Chloro-2-nitrophenyl)-5-[4-(propyloxy)phenyl]-1,3,4-oxadiazole