N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl]aniline

Wang, S.-W.; Zuo, Z.-Q.; Yang, W.-L.

doi:10.1107/S1600536807067402

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o353

doi:10.1107/S1600536807067402

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N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl]aniline

Shu-Wen Wang,^a ^* Zheng-Quan Zuo ^a and Wen-Long Yang ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: mosqito_001@163.com

(Received 15 November 2007; accepted 17 December 2007; online 4 January 2008)

In the molecule of the title compound, C₂₀H₁₉N₅O, the pyrazole and oxadiazole rings are not completely conjugated, the dihedral angle between them being 7.97 (6)°. The pyrazole and oxadiazole rings form dihedral angles of 42.74 (6) and 4.35 (5)° with the attached phenyl and benzene rings, respectively.

Related literature

For related literature, see: Ashton et al. (1993 ); Charles et al. (2004 ); Coswami et al. (1984 ); Wang et al. (2006 ).

Experimental

Crystal data

C₂₀H₁₉N₅O
M_r = 345.40
Monoclinic, P 2₁ /c
a = 17.746 (7) Å
b = 6.942 (3) Å
c = 14.474 (6) Å
β = 99.738 (5)°
V = 1757.6 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.28 × 0.20 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.993
9198 measured reflections
3096 independent reflections
2212 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.04
3096 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2000 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067402/rz2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067402/rz2184Isup2.hkl

checkCIF report

Comment top

In recent years, 1,3,4-oxadiazole derivatives have been extensively studied due to their broad biological activities, such as herbicidal, insecticidal and fungicidal activities (Coswami et al., 1984). Pyrazoles, as an important class of compounds in medicinal chemistry, constitute the basic framework of drugs in many pharmacological and medicinal applications (Ashton et al., 1993). Bis-heterocycles with high bioactivity have been reported in literature (Charles et al., 2004). In a continuation of our study on structure-activity relationship (Wang et al., 2006), we report here the crystal structure of the title compound (Fig.1), which was synthesized from N'-(4-(dimethylamino)benzylidene)-5-methyl-1-phenyl-1H-pyrazole-4 -carbohydrazide.

Most bond lengths and angles in the title compound are as expected for this type of compounds. The N4—C12 bond length (1.290 (2) Å) in the oxadiazole ring is shorter than the N2—C9 bond length (1.311 (2) Å) in the pyrazole ring, while the N3—N4 bond length (1.4140 (19) Å) is longer than the N1—N2 bond distance (1.3701 (18) Å). This could be ascribed to the strong electron withdrawing effect of the oxygen atom in the oxadiazole ring. In addition, because of the conjugated effect among oxygen and the two C=N bonds, the C—O bond lengths are shorter than the normal C—O single bond (1.42–1.46 Å). The pyrazole and oxadiazole rings are not completely conjugated, the dihedral angle between them being 7.97 (6)°. The dihedral angles formed by the pyrazole and oxadiazole rings with the attached phenyl and benzene rings are 42.74 (6) and 4.35 (5)° respectively.

Related literature top

For related literature, see: Ashton et al. (1993); Charles et al. (2004); Coswami et al. (1984); Wang et al. (2006).

Experimental top

A mixture of N'-(4-(dimethylamino)benzylidene)-5-methyl-1-phenyl-1H-pyrazole -4-carbohydrazide (0.694 g, 2 mmol), obtained according to a previously reported procedure (Wang et al., 2006), iodosobenzene diacetate (0.644 g, 2 mmol) and anhydrous ethanol (50 ml) was stirred in a 100 ml flask at room temperature for 2 h. The solid product formed was then filtered and washed with anhydrous ethanol. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (m.p. 488 K).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

Fig. 1. View of the title compound with 35% probability ellipsoid.

N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol- 2-yl]aniline top

Crystal data top

C₂₀H₁₉N₅O	F(000) = 728
M_r = 345.40	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2162 reflections
a = 17.746 (7) Å	θ = 2.3–23.1°
b = 6.942 (3) Å	µ = 0.09 mm⁻¹
c = 14.474 (6) Å	T = 293 K
β = 99.738 (5)°	Plate, colourless
V = 1757.6 (12) Å³	0.28 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3096 independent reflections
Radiation source: fine-focus sealed tube	2212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→20
T_min = 0.976, T_max = 0.993	k = −7→8
9198 measured reflections	l = −15→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0598P)² + 0.1148P] where P = (F_o² + 2F_c²)/3
3096 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₁₉N₅O	V = 1757.6 (12) Å³
M_r = 345.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.746 (7) Å	µ = 0.09 mm⁻¹
b = 6.942 (3) Å	T = 293 K
c = 14.474 (6) Å	0.28 × 0.20 × 0.08 mm
β = 99.738 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3096 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2212 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.993	R_int = 0.025
9198 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
3096 reflections	Δρ_min = −0.19 e Å⁻³
238 parameters

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
O1	0.23457 (6)	0.46275 (15)	0.97159 (7)	0.0441 (3)
N1	0.36081 (7)	0.98159 (18)	0.95277 (9)	0.0419 (3)
N2	0.35181 (8)	1.0599 (2)	1.03710 (9)	0.0519 (4)
N3	0.22892 (9)	0.5614 (2)	1.11520 (10)	0.0546 (4)
N4	0.18766 (9)	0.3870 (2)	1.09869 (10)	0.0554 (4)
N5	0.07036 (9)	−0.3315 (2)	0.82215 (11)	0.0683 (5)
C1	0.46094 (10)	1.2036 (2)	0.92564 (13)	0.0560 (5)
H1	0.4814	1.1998	0.9892	0.067*
C2	0.49418 (11)	1.3160 (3)	0.86493 (16)	0.0666 (6)
H2	0.5375	1.3882	0.8878	0.080*
C3	0.46404 (12)	1.3224 (3)	0.77106 (16)	0.0659 (6)
H3	0.4869	1.3984	0.7307	0.079*
C4	0.40026 (11)	1.2166 (2)	0.73698 (13)	0.0560 (5)
H4	0.3802	1.2199	0.6733	0.067*
C5	0.36550 (9)	1.1050 (2)	0.79661 (11)	0.0465 (4)
H5	0.3214	1.0361	0.7736	0.056*
C6	0.39648 (9)	1.0964 (2)	0.89030 (11)	0.0412 (4)
C7	0.32987 (9)	0.8024 (2)	0.93957 (10)	0.0400 (4)
C8	0.29830 (9)	0.7646 (2)	1.01870 (10)	0.0420 (4)
C9	0.31435 (10)	0.9277 (2)	1.07553 (12)	0.0516 (4)
H9	0.3000	0.9408	1.1341	0.062*
C10	0.33531 (11)	0.6795 (3)	0.85662 (12)	0.0558 (5)
H10A	0.2911	0.6998	0.8094	0.084*
H10B	0.3379	0.5465	0.8750	0.084*
H10C	0.3805	0.7130	0.8319	0.084*
C11	0.25474 (9)	0.5991 (2)	1.03925 (11)	0.0428 (4)
C12	0.19272 (9)	0.3352 (2)	1.01439 (11)	0.0427 (4)
C13	0.16085 (9)	0.1674 (2)	0.96261 (11)	0.0430 (4)
C14	0.17535 (9)	0.1234 (2)	0.87380 (12)	0.0471 (4)
H14	0.2054	0.2063	0.8450	0.057*
C15	0.14621 (9)	−0.0402 (3)	0.82743 (12)	0.0501 (4)
H15	0.1573	−0.0663	0.7681	0.060*
C16	0.10020 (9)	−0.1681 (2)	0.86788 (12)	0.0484 (4)
C17	0.08488 (10)	−0.1211 (3)	0.95697 (12)	0.0539 (5)
H17	0.0540	−0.2020	0.9856	0.065*
C18	0.11459 (10)	0.0419 (3)	1.00279 (12)	0.0519 (4)
H18	0.1036	0.0691	1.0620	0.062*
C19	0.09588 (13)	−0.4001 (3)	0.73912 (15)	0.0736 (6)
H19A	0.0894	−0.3005	0.6924	0.110*
H19B	0.0664	−0.5109	0.7155	0.110*
H19C	0.1489	−0.4349	0.7539	0.110*
C20	0.02076 (12)	−0.4574 (3)	0.86451 (16)	0.0731 (6)
H20A	0.0480	−0.5061	0.9228	0.110*
H20B	0.0047	−0.5631	0.8230	0.110*
H20C	−0.0233	−0.3866	0.8758	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0498 (6)	0.0455 (6)	0.0386 (6)	−0.0029 (5)	0.0125 (5)	0.0024 (5)
N1	0.0463 (8)	0.0422 (8)	0.0365 (8)	−0.0030 (6)	0.0049 (6)	−0.0006 (6)
N2	0.0677 (9)	0.0506 (8)	0.0369 (8)	−0.0056 (7)	0.0077 (7)	−0.0051 (6)
N3	0.0693 (10)	0.0535 (9)	0.0438 (9)	−0.0081 (8)	0.0180 (7)	−0.0004 (7)
N4	0.0689 (10)	0.0561 (9)	0.0450 (9)	−0.0106 (8)	0.0205 (7)	−0.0011 (7)
N5	0.0716 (11)	0.0739 (11)	0.0617 (10)	−0.0230 (9)	0.0175 (8)	−0.0193 (8)
C1	0.0505 (10)	0.0482 (10)	0.0648 (12)	−0.0017 (8)	−0.0034 (9)	0.0090 (9)
C2	0.0499 (11)	0.0521 (11)	0.0978 (17)	−0.0068 (9)	0.0128 (11)	0.0138 (11)
C3	0.0708 (14)	0.0469 (11)	0.0880 (16)	0.0084 (10)	0.0362 (12)	0.0188 (10)
C4	0.0711 (13)	0.0479 (10)	0.0527 (11)	0.0103 (9)	0.0217 (9)	0.0107 (8)
C5	0.0489 (10)	0.0443 (9)	0.0468 (10)	0.0035 (8)	0.0094 (8)	0.0035 (8)
C6	0.0415 (9)	0.0371 (9)	0.0453 (10)	0.0027 (7)	0.0079 (7)	0.0052 (7)
C7	0.0410 (9)	0.0387 (9)	0.0395 (9)	0.0031 (7)	0.0045 (7)	0.0005 (7)
C8	0.0458 (9)	0.0429 (9)	0.0367 (9)	0.0017 (7)	0.0054 (7)	0.0032 (7)
C9	0.0653 (11)	0.0541 (11)	0.0359 (9)	−0.0042 (9)	0.0102 (8)	0.0012 (8)
C10	0.0702 (12)	0.0481 (10)	0.0536 (11)	−0.0042 (9)	0.0239 (9)	−0.0066 (8)
C11	0.0469 (9)	0.0444 (9)	0.0367 (9)	0.0044 (7)	0.0060 (7)	0.0023 (7)
C12	0.0431 (9)	0.0465 (9)	0.0405 (9)	0.0017 (7)	0.0124 (7)	0.0081 (7)
C13	0.0439 (9)	0.0466 (9)	0.0396 (9)	0.0023 (7)	0.0103 (7)	0.0043 (7)
C14	0.0442 (9)	0.0541 (10)	0.0457 (10)	0.0002 (8)	0.0148 (7)	0.0077 (8)
C15	0.0495 (10)	0.0626 (11)	0.0399 (10)	0.0008 (9)	0.0127 (8)	−0.0014 (8)
C16	0.0435 (9)	0.0570 (10)	0.0440 (10)	−0.0014 (8)	0.0052 (7)	−0.0016 (8)
C17	0.0548 (10)	0.0601 (11)	0.0494 (11)	−0.0138 (9)	0.0163 (8)	0.0006 (9)
C18	0.0590 (11)	0.0586 (11)	0.0418 (10)	−0.0081 (9)	0.0192 (8)	−0.0008 (8)
C19	0.0827 (14)	0.0702 (13)	0.0685 (14)	−0.0006 (11)	0.0145 (11)	−0.0198 (11)
C20	0.0697 (13)	0.0660 (13)	0.0822 (15)	−0.0179 (11)	0.0089 (11)	−0.0085 (11)

Geometric parameters (Å, º) top

O1—C11	1.3656 (19)	C7—C10	1.489 (2)
O1—C12	1.3694 (18)	C8—C9	1.400 (2)
N1—C7	1.360 (2)	C8—C11	1.443 (2)
N1—N2	1.3701 (18)	C9—H9	0.9300
N1—C6	1.431 (2)	C10—H10A	0.9600
N2—C9	1.311 (2)	C10—H10B	0.9600
N3—C11	1.287 (2)	C10—H10C	0.9600
N3—N4	1.4140 (19)	C12—C13	1.447 (2)
N4—C12	1.290 (2)	C13—C14	1.387 (2)
N5—C16	1.374 (2)	C13—C18	1.390 (2)
N5—C19	1.435 (2)	C14—C15	1.375 (2)
N5—C20	1.448 (2)	C14—H14	0.9300
C1—C2	1.380 (3)	C15—C16	1.400 (2)
C1—C6	1.388 (2)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.401 (2)
C2—C3	1.374 (3)	C17—C18	1.371 (2)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.369 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—H19A	0.9600
C4—C5	1.380 (2)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.376 (2)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C7—C8	1.383 (2)	C20—H20C	0.9600

C11—O1—C12	102.73 (12)	C7—C10—H10C	109.5
C7—N1—N2	112.53 (13)	H10A—C10—H10C	109.5
C7—N1—C6	129.20 (13)	H10B—C10—H10C	109.5
N2—N1—C6	118.20 (13)	N3—C11—O1	112.53 (14)
C9—N2—N1	104.12 (13)	N3—C11—C8	128.20 (15)
C11—N3—N4	106.20 (14)	O1—C11—C8	119.24 (13)
C12—N4—N3	106.35 (13)	N4—C12—O1	112.19 (14)
C16—N5—C19	121.80 (16)	N4—C12—C13	129.10 (15)
C16—N5—C20	120.45 (16)	O1—C12—C13	118.71 (14)
C19—N5—C20	117.04 (16)	C14—C13—C18	117.70 (15)
C2—C1—C6	118.87 (18)	C14—C13—C12	122.67 (15)
C2—C1—H1	120.6	C18—C13—C12	119.63 (15)
C6—C1—H1	120.6	C15—C14—C13	121.40 (15)
C3—C2—C1	120.74 (19)	C15—C14—H14	119.3
C3—C2—H2	119.6	C13—C14—H14	119.3
C1—C2—H2	119.6	C14—C15—C16	121.18 (16)
C4—C3—C2	119.91 (18)	C14—C15—H15	119.4
C4—C3—H3	120.0	C16—C15—H15	119.4
C2—C3—H3	120.0	N5—C16—C15	121.80 (16)
C3—C4—C5	120.35 (18)	N5—C16—C17	121.12 (16)
C3—C4—H4	119.8	C15—C16—C17	117.07 (16)
C5—C4—H4	119.8	C18—C17—C16	121.26 (16)
C6—C5—C4	119.63 (17)	C18—C17—H17	119.4
C6—C5—H5	120.2	C16—C17—H17	119.4
C4—C5—H5	120.2	C17—C18—C13	121.39 (16)
C5—C6—C1	120.47 (15)	C17—C18—H18	119.3
C5—C6—N1	120.09 (14)	C13—C18—H18	119.3
C1—C6—N1	119.40 (15)	N5—C19—H19A	109.5
N1—C7—C8	105.52 (13)	N5—C19—H19B	109.5
N1—C7—C10	123.88 (14)	H19A—C19—H19B	109.5
C8—C7—C10	130.53 (15)	N5—C19—H19C	109.5
C7—C8—C9	105.22 (14)	H19A—C19—H19C	109.5
C7—C8—C11	128.89 (14)	H19B—C19—H19C	109.5
C9—C8—C11	125.83 (15)	N5—C20—H20A	109.5
N2—C9—C8	112.60 (15)	N5—C20—H20B	109.5
N2—C9—H9	123.7	H20A—C20—H20B	109.5
C8—C9—H9	123.7	N5—C20—H20C	109.5
C7—C10—H10A	109.5	H20A—C20—H20C	109.5
C7—C10—H10B	109.5	H20B—C20—H20C	109.5
H10A—C10—H10B	109.5

C7—N1—N2—C9	−0.54 (17)	C12—O1—C11—N3	0.19 (16)
C6—N1—N2—C9	176.53 (13)	C12—O1—C11—C8	−178.00 (13)
C11—N3—N4—C12	0.29 (18)	C7—C8—C11—N3	176.18 (16)
C6—C1—C2—C3	0.1 (3)	C9—C8—C11—N3	−7.0 (3)
C1—C2—C3—C4	0.1 (3)	C7—C8—C11—O1	−5.9 (2)
C2—C3—C4—C5	0.7 (3)	C9—C8—C11—O1	170.91 (15)
C3—C4—C5—C6	−1.7 (2)	N3—N4—C12—O1	−0.18 (18)
C4—C5—C6—C1	2.0 (2)	N3—N4—C12—C13	−179.99 (15)
C4—C5—C6—N1	179.85 (14)	C11—O1—C12—N4	0.01 (16)
C2—C1—C6—C5	−1.2 (3)	C11—O1—C12—C13	179.84 (13)
C2—C1—C6—N1	−179.07 (16)	N4—C12—C13—C14	−175.58 (17)
C7—N1—C6—C5	41.8 (2)	O1—C12—C13—C14	4.6 (2)
N2—N1—C6—C5	−134.74 (15)	N4—C12—C13—C18	3.4 (3)
C7—N1—C6—C1	−140.34 (17)	O1—C12—C13—C18	−176.37 (14)
N2—N1—C6—C1	43.1 (2)	C18—C13—C14—C15	−1.1 (2)
N2—N1—C7—C8	0.98 (17)	C12—C13—C14—C15	177.95 (15)
C6—N1—C7—C8	−175.69 (14)	C13—C14—C15—C16	0.5 (2)
N2—N1—C7—C10	−176.36 (14)	C19—N5—C16—C15	12.1 (3)
C6—N1—C7—C10	7.0 (2)	C20—N5—C16—C15	−177.81 (17)
N1—C7—C8—C9	−0.98 (16)	C19—N5—C16—C17	−168.77 (18)
C10—C7—C8—C9	176.12 (17)	C20—N5—C16—C17	1.3 (3)
N1—C7—C8—C11	176.38 (15)	C14—C15—C16—N5	179.64 (16)
C10—C7—C8—C11	−6.5 (3)	C14—C15—C16—C17	0.5 (2)
N1—N2—C9—C8	−0.13 (19)	N5—C16—C17—C18	180.00 (17)
C7—C8—C9—N2	0.72 (19)	C15—C16—C17—C18	−0.8 (3)
C11—C8—C9—N2	−176.75 (14)	C16—C17—C18—C13	0.2 (3)
N4—N3—C11—O1	−0.30 (18)	C14—C13—C18—C17	0.7 (2)
N4—N3—C11—C8	177.69 (15)	C12—C13—C18—C17	−178.34 (16)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₅O
M_r	345.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.746 (7), 6.942 (3), 14.474 (6)
β (°)	99.738 (5)
V (Å³)	1757.6 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.20 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	9198, 3096, 2212
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.04
No. of reflections	3096
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.19

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Acknowledgements

This project was supported by the National Science Foundation of China (No. 20572057) and the Natural Science Foundation of Shandong Province (No. Y2006B11)

References

Ashton, W. T., Hutchins, S. M., Greenlee, W. J., Doss, G. A., Chang, R. S. L., Lotti, V. J., Faust, K. A., Chen, T. B., Zingaro, G. J., Kivlighn, S. D. & Siegl, P. K. S. (1993). J. Med. Chem. 36, 3595–3605. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Charles, Q., Huang, K. M. & Wilcoxen, D. E. (2004). Bioorg. Med. Chem. Lett. 14, 3943–3947. Web of Science PubMed Google Scholar
Coswami, B. N., Kataky, J. C. S. & Baruash, J. N. (1984). J. Heterocycl. Chem. 21, 205–208. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Wang, S.-W., Wen, L.-R. & Miao, Y.-F. (2006). Acta Cryst. E62, o3471–o3472. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

N,N-Di­methyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxa­diazol-2-yl]aniline

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl]aniline