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

Fun, H.-K.; Sumangala, V.; Nagaraja, G.K.; Poojary, B.; Chantrapromma, S.

doi:10.1107/S1600536811001504

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o420-o421

doi:10.1107/S1600536811001504

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

Hoong-Kun Fun,^a ^*‡ V. Sumangala,^b G. K. Nagaraja,^b Boja Poojary ^b and Suchada Chantrapromma ^c §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Karnatak State, India, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 28 December 2010; accepted 11 January 2011; online 15 January 2011)

In the title 1,2,4-oxadiazole derivative, C₁₉H₁₈ClN₃O₃, the 1,2,4-oxadiazole ring makes dihedral angles of 12.83 (8) and 4.89 (8)°, respectively, with the benzyl and 4-chlorophenyl rings, while the dihedral angle between the benzyl and 4-chlorophenyl rings is 11.53 (7)°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into helical chains along the b axis. A weak C—H⋯π interaction 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_r = 371.81
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 1.02
4556 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1950 Friedel pairs
Flack parameter: 0.01 (6)

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) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The 1,2,4-oxadiazole ring occurs frequently in biologically active synthetic compounds and 1,2,4-oxadiazole derivatives are suggested as potential agonists for cortical muscarinic (Saunders et al., 1990; Showell et al., 1991), benzodiazepine (Watjen et al., 1989; Tully et al., 1991) and 5-HT1D (5-hydroxytryptamine) as receptors (Chen et al., 1994) as well as antagonists for 5-HT3 (Swain et al., 1991) or histamine H3 receptors (Clitherow et al., 1996). They also demonstrate anti-inflammatory (Nicolaides et al., 1998) and antitumor activities (Chimirri et al., 1996). These interesting and important properties of 1,2,4-oxadiazole derivatives lead us to synthesize the title compound (I) and its crystal structure was reported.

In the molecule of (I), (Fig. 1), the 1,2,4-oxadiazole ring is nearly co-planar with the 4-chlorophenyl with a dihedral angle between the two rings being 4.89 (8)°, whereas it is inclined to the benzyl (C11–C17) unit with a dihedral angle of 12.48 (9)°. The dihedral angle between the benzyl group and the phenyl (C1–C6) ring is 11.53 (7)°. The oxycarbonylamino unit (atoms C10, N3, O2 and O3) is planar with an r.m.s. 0.0009 (1) Å. This unit makes dihedral angles of 79.99 (9), 89.15 (9) and 89.64 (9)°, respectively, with the benzyl, 1,2,4-oxadiazole and 4-chlorophenyl rings. The bond distances are of normal values (Allen et al., 1987) and are comparable to the related structure (Fun et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by by N—H···N hydrogen bonds (Table 1) into helical chains along the b axis. The crystal is stabilized by N—H···O hydrogen bonds and weak C—H···π interactions (Table 1).

Related literature top

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 top

The title compound was synthesized by taking benzyl [(2E)-2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate (0.1 mole) in 5 mol volume of pyridine and treated with 0.1 mole of 4-chlorobenzoylchloride. The reaction mixture is heated to reflux for 3–4 hrs. After the reaction is completed, the excess pyridine is distilled out under low pressure and the resultant quenched onto ice water. The solid thus formed is filtered and washed with water. The sample is dried and recrystallized in ethanol yielding 95% product. Colorless plate-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days (m.p. 405–409 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, showing helical chains along the b axis. N—H···N hydrogen bonds are shown as dashed lines.

Benzyl N-{2-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]propan-2-yl}carbamate top

Crystal data top

C₁₉H₁₈ClN₃O₃	D_x = 1.380 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0458P)² + 0.0092P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4556 reflections	Δρ_max = 0.14 e Å⁻³
241 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1950 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (6)

Crystal data top

C₁₉H₁₈ClN₃O₃	V = 1789.70 (5) Å³
M_r = 371.81	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7501 (1) Å	µ = 0.24 mm⁻¹
b = 11.0052 (2) Å	T = 297 K
c = 20.9834 (3) Å	0.41 × 0.35 × 0.21 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4556 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3620 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.951	R_int = 0.028
15995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	Δρ_max = 0.14 e Å⁻³
S = 1.02	Δρ_min = −0.21 e Å⁻³
4556 reflections	Absolute structure: Flack (1983), 1950 Friedel pairs
241 parameters	Absolute structure parameter: 0.01 (6)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+1/2; (ii) −x−1, y+3/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈ClN₃O₃
M_r	371.81
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	297
a, b, c (Å)	7.7501 (1), 11.0052 (2), 20.9834 (3)
V (Å³)	1789.70 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.41 × 0.35 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.908, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	15995, 4556, 3620
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 1.02
No. of reflections	4556
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21
Absolute structure	Flack (1983), 1950 Friedel pairs
Absolute structure parameter	0.01 (6)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+1/2; (ii) −x−1, y+3/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

VS, GKN and BP thank Mangalore University for a research grant. SC thanks the Prince of Songkla University for generous support. The authors thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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Volume 67| Part 2| February 2011| Pages o420-o421

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