Benzyl N-{2-[5-(4-chloro-phen-yl)-1,2,4-oxadiazol-3-yl]propan-2-yl}carbamate.

In the title 1,2,4-oxadiazole derivative, C(19)H(18)ClN(3)O(3), the 1,2,4-oxadiazole ring makes dihedral angles of 12.83 (8) and 4.89 (8)°, respectively, with the benzyl and 4-chloro-phenyl rings, while the dihedral angle between the benzyl and 4-chloro-phenyl rings is 11.53 (7)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into helical chains along the b axis. A weak C-H⋯π inter-action is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and applications of 1,2,4-oxadiazole derivatives, see: Chen et al. (1994 ▶); Chimirri et al. (1996 ▶); Clitherow et al. (1996 ▶); Nicolaides et al. (1998 ▶); Saunders et al. (1990 ▶); Showell et al. (1991 ▶); Swain et al. (1991 ▶); Tully et al. (1991 ▶); Watjen et al. (1989 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C19H18ClN3O3

M = 371.81

Orthorhombic,

a = 7.7501 (1) Å

b = 11.0052 (2) Å

c = 20.9834 (3) Å

V = 1789.70 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 297 K

0.41 × 0.35 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.908, T max = 0.951

15995 measured reflections

4556 independent reflections

3620 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.087

S = 1.02

4556 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1950 Friedel pairs

Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001504/is2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001504/is2659Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H18ClN3O3	Dx = 1.380 Mg m−3
Mr = 371.81	Melting point = 405–409 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4556 reflections
a = 7.7501 (1) Å	θ = 1.9–28.5°
b = 11.0052 (2) Å	µ = 0.24 mm−1
c = 20.9834 (3) Å	T = 297 K
V = 1789.70 (5) Å3	Plate, colorless
Z = 4	0.41 × 0.35 × 0.21 mm
F(000) = 776

Bruker APEXII CCD area-detector diffractometer	4556 independent reflections
Radiation source: sealed tube	3620 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→8
Tmin = 0.908, Tmax = 0.951	k = −14→14
15995 measured reflections	l = −23→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.0092P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4556 reflections	Δρmax = 0.14 e Å−3
241 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 1950 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq
Cl1	1.06337 (9)	0.74415 (5)	−0.14993 (2)	0.08010 (19)
O1	0.90644 (16)	0.42996 (9)	0.11883 (5)	0.0490 (3)
O2	0.62272 (16)	0.60054 (11)	0.29142 (7)	0.0631 (4)
O3	0.71211 (14)	0.79437 (9)	0.30763 (6)	0.0501 (3)
N1	1.00418 (18)	0.59694 (10)	0.16396 (6)	0.0422 (3)
N2	0.89957 (19)	0.41084 (11)	0.18577 (6)	0.0487 (3)
N3	0.90781 (17)	0.65050 (11)	0.29774 (6)	0.0401 (3)
C1	1.0718 (2)	0.70094 (14)	0.03799 (7)	0.0470 (4)
H1A	1.1094	0.7446	0.0733	0.056*
C2	1.0945 (2)	0.74801 (15)	−0.02232 (8)	0.0522 (4)
H2A	1.1470	0.8233	−0.0279	0.063*
C3	1.0385 (2)	0.68209 (16)	−0.07420 (7)	0.0499 (4)
C4	0.9627 (2)	0.56952 (14)	−0.06747 (8)	0.0517 (4)
H4A	0.9283	0.5255	−0.1031	0.062*
C5	0.9386 (2)	0.52308 (13)	−0.00694 (7)	0.0469 (4)
H5A	0.8859	0.4478	−0.0017	0.056*
C6	0.9930 (2)	0.58868 (12)	0.04632 (7)	0.0393 (3)
C7	0.96954 (19)	0.54258 (12)	0.11114 (7)	0.0386 (3)
C8	0.9582 (2)	0.51195 (12)	0.20882 (7)	0.0371 (3)
C9	0.9872 (2)	0.53376 (12)	0.27932 (7)	0.0417 (4)
C10	0.7365 (2)	0.67374 (13)	0.29808 (7)	0.0414 (3)
C11	0.5372 (2)	0.83404 (16)	0.32187 (8)	0.0528 (4)
H11A	0.4552	0.7744	0.3064	0.063*
H11B	0.5141	0.9106	0.3007	0.063*
C12	0.51699 (19)	0.84918 (13)	0.39282 (7)	0.0423 (3)
C13	0.5898 (2)	0.94799 (14)	0.42406 (9)	0.0545 (4)
H13A	0.6480	1.0070	0.4008	0.065*
C14	0.5766 (3)	0.95920 (16)	0.48927 (9)	0.0621 (5)
H14A	0.6270	1.0253	0.5096	0.074*
C15	0.4903 (3)	0.87436 (17)	0.52416 (9)	0.0591 (5)
H15A	0.4826	0.8825	0.5682	0.071*
C16	0.4146 (2)	0.77656 (16)	0.49429 (8)	0.0572 (4)
H16A	0.3541	0.7191	0.5179	0.069*
C17	0.4292 (2)	0.76457 (13)	0.42877 (8)	0.0496 (4)
H17A	0.3788	0.6981	0.4087	0.060*
C18	1.1805 (2)	0.54871 (16)	0.28978 (9)	0.0562 (5)
H18A	1.2220	0.6155	0.2647	0.084*
H18B	1.2389	0.4756	0.2773	0.084*
H18C	1.2024	0.5645	0.3340	0.084*
C19	0.9170 (3)	0.42786 (14)	0.31875 (8)	0.0592 (5)
H19A	0.7970	0.4162	0.3092	0.089*
H19B	0.9302	0.4456	0.3633	0.089*
H19C	0.9799	0.3552	0.3085	0.089*
H1N3	0.973 (2)	0.7115 (14)	0.2985 (7)	0.036 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.1106 (5)	0.0857 (4)	0.0440 (2)	0.0012 (3)	0.0132 (3)	0.0075 (2)
O1	0.0635 (7)	0.0416 (5)	0.0418 (6)	−0.0124 (5)	−0.0050 (6)	−0.0044 (4)
O2	0.0508 (7)	0.0552 (7)	0.0833 (10)	−0.0086 (6)	−0.0013 (7)	0.0010 (6)
O3	0.0486 (7)	0.0433 (5)	0.0584 (7)	0.0076 (5)	0.0118 (6)	0.0012 (5)
N1	0.0508 (8)	0.0373 (6)	0.0384 (7)	−0.0039 (5)	0.0004 (6)	−0.0046 (5)
N2	0.0609 (9)	0.0431 (7)	0.0422 (7)	−0.0097 (6)	−0.0013 (7)	−0.0010 (5)
N3	0.0438 (8)	0.0338 (6)	0.0425 (7)	−0.0013 (6)	0.0046 (6)	−0.0040 (5)
C1	0.0536 (10)	0.0451 (8)	0.0422 (8)	−0.0064 (7)	−0.0001 (8)	−0.0097 (6)
C2	0.0575 (10)	0.0478 (8)	0.0514 (9)	−0.0079 (8)	0.0081 (8)	−0.0012 (7)
C3	0.0530 (10)	0.0577 (9)	0.0389 (8)	0.0070 (8)	0.0062 (8)	−0.0006 (7)
C4	0.0598 (11)	0.0534 (9)	0.0420 (8)	0.0038 (8)	−0.0090 (8)	−0.0110 (7)
C5	0.0536 (11)	0.0415 (8)	0.0457 (8)	−0.0013 (7)	−0.0070 (8)	−0.0065 (6)
C6	0.0399 (8)	0.0388 (7)	0.0390 (8)	0.0034 (6)	0.0000 (7)	−0.0060 (5)
C7	0.0376 (8)	0.0352 (7)	0.0431 (8)	−0.0002 (6)	−0.0026 (7)	−0.0057 (6)
C8	0.0374 (8)	0.0328 (6)	0.0410 (7)	0.0000 (6)	0.0007 (6)	−0.0021 (5)
C9	0.0507 (10)	0.0357 (7)	0.0389 (8)	0.0043 (6)	0.0017 (7)	−0.0032 (6)
C10	0.0496 (9)	0.0419 (7)	0.0327 (7)	0.0033 (7)	0.0047 (7)	0.0044 (6)
C11	0.0474 (10)	0.0591 (10)	0.0518 (10)	0.0146 (8)	0.0031 (8)	0.0053 (7)
C12	0.0345 (8)	0.0425 (7)	0.0499 (9)	0.0088 (6)	0.0019 (7)	0.0026 (6)
C13	0.0503 (10)	0.0438 (8)	0.0692 (12)	−0.0025 (8)	0.0048 (9)	0.0023 (8)
C14	0.0618 (12)	0.0539 (10)	0.0705 (12)	0.0008 (9)	−0.0075 (11)	−0.0185 (8)
C15	0.0585 (12)	0.0680 (11)	0.0507 (10)	0.0107 (9)	0.0034 (9)	−0.0074 (8)
C16	0.0589 (11)	0.0567 (10)	0.0561 (10)	−0.0002 (9)	0.0101 (9)	0.0080 (7)
C17	0.0506 (10)	0.0423 (8)	0.0560 (9)	−0.0043 (8)	0.0001 (8)	−0.0035 (7)
C18	0.0540 (11)	0.0618 (10)	0.0528 (10)	0.0117 (8)	−0.0128 (9)	−0.0138 (8)
C19	0.0924 (15)	0.0401 (8)	0.0452 (9)	0.0039 (9)	0.0064 (10)	0.0028 (6)

Cl1—C3	1.7404 (16)	C8—C9	1.515 (2)
O1—C7	1.3422 (16)	C9—C18	1.523 (2)
O1—N2	1.4213 (17)	C9—C19	1.529 (2)
O2—C10	1.2023 (19)	C11—C12	1.506 (2)
O3—C10	1.3558 (18)	C11—H11A	0.9700
O3—C11	1.455 (2)	C11—H11B	0.9700
N1—C7	1.2877 (18)	C12—C17	1.378 (2)
N1—C8	1.3740 (19)	C12—C13	1.390 (2)
N2—C8	1.2955 (18)	C13—C14	1.378 (3)
N3—C10	1.352 (2)	C13—H13A	0.9300
N3—C9	1.4758 (18)	C14—C15	1.362 (3)
N3—H1N3	0.841 (16)	C14—H14A	0.9300
C1—C2	1.379 (2)	C15—C16	1.377 (3)
C1—C6	1.389 (2)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.386 (2)
C2—C3	1.378 (2)	C16—H16A	0.9300
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.378 (2)	C18—H18A	0.9600
C4—C5	1.382 (2)	C18—H18B	0.9600
C4—H4A	0.9300	C18—H18C	0.9600
C5—C6	1.3957 (19)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C6—C7	1.463 (2)	C19—H19C	0.9600
C7—O1—N2	105.61 (10)	O2—C10—O3	124.84 (16)
C10—O3—C11	116.99 (13)	N3—C10—O3	108.82 (14)
C7—N1—C8	102.66 (12)	O3—C11—C12	109.46 (13)
C8—N2—O1	103.21 (11)	O3—C11—H11A	109.8
C10—N3—C9	125.11 (13)	C12—C11—H11A	109.8
C10—N3—H1N3	116.2 (10)	O3—C11—H11B	109.8
C9—N3—H1N3	116.6 (10)	C12—C11—H11B	109.8
C2—C1—C6	120.39 (14)	H11A—C11—H11B	108.2
C2—C1—H1A	119.8	C17—C12—C13	118.11 (15)
C6—C1—H1A	119.8	C17—C12—C11	121.18 (14)
C3—C2—C1	119.14 (15)	C13—C12—C11	120.70 (15)
C3—C2—H2A	120.4	C14—C13—C12	120.56 (16)
C1—C2—H2A	120.4	C14—C13—H13A	119.7
C2—C3—C4	121.76 (15)	C12—C13—H13A	119.7
C2—C3—Cl1	118.67 (13)	C15—C14—C13	120.61 (17)
C4—C3—Cl1	119.56 (13)	C15—C14—H14A	119.7
C3—C4—C5	118.97 (14)	C13—C14—H14A	119.7
C3—C4—H4A	120.5	C14—C15—C16	120.02 (18)
C5—C4—H4A	120.5	C14—C15—H15A	120.0
C4—C5—C6	120.26 (15)	C16—C15—H15A	120.0
C4—C5—H5A	119.9	C15—C16—C17	119.42 (16)
C6—C5—H5A	119.9	C15—C16—H16A	120.3
C1—C6—C5	119.47 (14)	C17—C16—H16A	120.3
C1—C6—C7	118.68 (13)	C12—C17—C16	121.27 (15)
C5—C6—C7	121.84 (14)	C12—C17—H17A	119.4
N1—C7—O1	113.68 (13)	C16—C17—H17A	119.4
N1—C7—C6	127.82 (13)	C9—C18—H18A	109.5
O1—C7—C6	118.50 (12)	C9—C18—H18B	109.5
N2—C8—N1	114.83 (13)	H18A—C18—H18B	109.5
N2—C8—C9	123.53 (13)	C9—C18—H18C	109.5
N1—C8—C9	121.50 (12)	H18A—C18—H18C	109.5
N3—C9—C8	109.39 (12)	H18B—C18—H18C	109.5
N3—C9—C18	106.14 (13)	C9—C19—H19A	109.5
C8—C9—C18	107.66 (13)	C9—C19—H19B	109.5
N3—C9—C19	111.94 (13)	H19A—C19—H19B	109.5
C8—C9—C19	110.79 (12)	C9—C19—H19C	109.5
C18—C9—C19	110.72 (15)	H19A—C19—H19C	109.5
O2—C10—N3	126.34 (14)	H19B—C19—H19C	109.5
C7—O1—N2—C8	−0.08 (16)	C10—N3—C9—C18	−177.07 (15)
C6—C1—C2—C3	−0.2 (3)	C10—N3—C9—C19	−56.2 (2)
C1—C2—C3—C4	−1.0 (3)	N2—C8—C9—N3	−131.00 (16)
C1—C2—C3—Cl1	178.49 (14)	N1—C8—C9—N3	53.48 (19)
C2—C3—C4—C5	1.6 (3)	N2—C8—C9—C18	114.08 (17)
Cl1—C3—C4—C5	−177.88 (13)	N1—C8—C9—C18	−61.44 (18)
C3—C4—C5—C6	−1.0 (3)	N2—C8—C9—C19	−7.1 (2)
C2—C1—C6—C5	0.7 (2)	N1—C8—C9—C19	177.35 (15)
C2—C1—C6—C7	−179.32 (15)	C9—N3—C10—O2	9.9 (3)
C4—C5—C6—C1	−0.1 (2)	C9—N3—C10—O3	−170.43 (13)
C4—C5—C6—C7	179.93 (15)	C11—O3—C10—O2	11.3 (2)
C8—N1—C7—O1	−0.38 (18)	C11—O3—C10—N3	−168.37 (12)
C8—N1—C7—C6	−179.60 (15)	C10—O3—C11—C12	98.05 (16)
N2—O1—C7—N1	0.30 (18)	O3—C11—C12—C17	−104.15 (17)
N2—O1—C7—C6	179.60 (13)	O3—C11—C12—C13	74.49 (18)
C1—C6—C7—N1	4.6 (2)	C17—C12—C13—C14	1.1 (2)
C5—C6—C7—N1	−175.44 (16)	C11—C12—C13—C14	−177.57 (16)
C1—C6—C7—O1	−174.60 (14)	C12—C13—C14—C15	−0.7 (3)
C5—C6—C7—O1	5.4 (2)	C13—C14—C15—C16	−0.3 (3)
O1—N2—C8—N1	−0.16 (18)	C14—C15—C16—C17	0.9 (3)
O1—N2—C8—C9	−175.95 (14)	C13—C12—C17—C16	−0.5 (2)
C7—N1—C8—N2	0.33 (19)	C11—C12—C17—C16	178.18 (15)
C7—N1—C8—C9	176.22 (14)	C15—C16—C17—C12	−0.5 (3)
C10—N3—C9—C8	67.03 (18)

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2i	0.840 (16)	2.428 (15)	3.2492 (18)	165.7 (14)
C16—H16A···Cg1ii	0.93	2.91	3.6700 (18)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2i	0.840 (16)	2.428 (15)	3.2492 (18)	165.7 (14)
C16—H16A⋯Cg1ii	0.93	2.91	3.6700 (18)	140

Symmetry codes: (i) ; (ii) .