4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl­idene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Fun, H.-K.; Hemamalini, M.; Asiri, A.M.; Khan, S.A.

doi:10.1107/S1600536810021173

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1602-o1603

doi:10.1107/S1600536810021173

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4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Abdullah M. Asiri ^b § and Salman A. Khan ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, King Abdu Aziz University, Jeddah, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 31 May 2010; accepted 3 June 2010; online 9 June 2010)

The title Schiff base compound, C₂₃H₂₃N₅O, was synthesized by the reaction of 4-aminophenazone and 3,5-dimethyl-1-phenylpyrazole-4-carbaxaldehyde. The molecule adopts an E configuration about the central C=N double bond. A weak intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the pyrazole rings is 24.72 (10)° and the dihedral angles between the pyrazole rings and the adjacent phenyl rings are 58.67 (10) and 46.58 (11)°. The crystal structure is stabilized by weak C—H⋯π interactions involving the pyrazolone and phenyl rings.

Related literature

For background to and applications of heterocylic Schiff bases, see: Nawaz et al. (2009 ); Li et al. (1999 ); Urena et al. (2003 ); Geronikaki et al. (2003 ); Shanker et al. (2009 ); Pandeya et al. (1999 ); Sridhar et al. (2002 ); Nawrocka et al. (2004 ). For related structures, see: Eryigit & Kendi (1998 ); Manikandan et al. (2000 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₂₃N₅O
M_r = 385.46
Monoclinic, P 2₁ /c
a = 15.2985 (2) Å
b = 7.6827 (1) Å
c = 19.6737 (3) Å
β = 116.905 (1)°
V = 2062.03 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.45 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.965, T_max = 0.992
23014 measured reflections
5993 independent reflections
2881 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.161
S = 1.03
5993 reflections
311 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4/N5/C11–C13 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1	0.986 (18)	2.40 (2)	3.052 (3)	123.3 (14)
C19—H19A⋯Cg2ⁱ	0.990 (19)	2.656 (19)	3.452 (2)	137.4 (17)
C20—H20C⋯Cg1ⁱⁱ	0.96	2.85 (3)	3.720 (3)	149 (1)
C22—H22B⋯Cg2ⁱⁱⁱ	0.96	2.82 (3)	3.585 (3)	135 (1)
Symmetry codes: (i) -x+1, -y-1, -z-1; (ii) -x, -y-2, -z-1; (iii) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536810021173/lh5060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021173/lh5060Isup2.hkl

checkCIF report

Comment top

Heterocyclic Schiff bases have attracted continuing interest over the years because of their varied biological activities (Nawaz et al., 2009). Recently they have found application in drug development for the treatment of allergies (Li et al., 1999), hypertension (Urena et al., 2003), inflammation (Geronikaki et al., 20003), bacterial (Shanker et al., 2009), HIV infections (Pandeya et al., 1999) and hypnotics (Sridhar et al., 2002). More recently they have also been used for the treatment of pain acting as fibrinogen receptor antagonists with antithrombotic activity (Nawrocka et al., 2004). Due to wide application of pyrazoline-containing Schiff bases, we have synthesized a novel pyrazoline-containing Schiff base from 4-aminophenazone.

In the title compound (Fig. 1), the rings A (C14–C19), B (N4/N5/C11–C13), C (N1/N2/C7–C9) and D (C1–C6) are essentially planar. The dihedral angle between the best planes of the rings are A/B = 58.67 (10)°, A/C = 83.07 (10)°, A/D = 79.53 (12)°, B/C = 24.72 (10)°, B/D = 44.68 (11)° and C/D = 46.58 (11)°. The molecule adopts a trans configuration about the central C10═N3 double bond. The C–N bond lengths of N1–C6 = 1.423 (2) Å; N2–C8 = 1.375 (2) Å; N3–C9 = 1.400 (2) Å; N5–C13 = 1.357 (2) Å; N1–C7 = 1.404 (2) Å; N2–C20 = 1.467 (2) Å; N4–C12 = 1.325 (2) Å and N5–C14 = 1.429 (2) are normal for C–N single-bond distances. The distance between C10–N3 (1.287 (2) Å) is typical for a C═N double-bond distance. These bonds are comparable with those in N-(1H-benzoimidazol-2-ylmethyl)-N-(2,6-dichlorophenyl) amine (Eryigit & Kendi, 1998). The N1–N2 and N4–N5 (1.4082 (19) Å & 1.3702 (19) Å) single-bond lengths are comparable with those in 2,6-bis(3,5-dimethylpyrazol-1-ylmethyl) pyridine (Manikandan et al., 2000). An weak intramolecular C10—H10A···O1 hydrogen bond interaction generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure (Fig. 2) there are no classical hydrogen bonds but stabilization is provided by weak C20—H20C···Cg1ⁱ, C19—H19A···Cg2ⁱⁱ and C22—H22B···Cg2ⁱⁱⁱ interactions (see Table 1 for symmetry codes). Cg1 and Cg2 are the centroids of rings (N4/N5/C11–C13) and (C1–C6) rings respectively.

Related literature top

For background to and applications of heterocylic Schiff bases, see: Nawaz et al. (2009); Li et al. (1999); Urena et al. (2003); Geronikaki et al. (2003); Shanker et al. (2009); Pandeya et al. (1999); Sridhar et al. (2002); Nawrocka et al. (2004). For related structures, see: Eryigit & Kendi (1998); Manikandan et al. (2000). For details of hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4-aminophenazone (0.50g, 0.0025 mol) and 3,5-dimethyl-1- phenylpyrazole-4-carbaxaldehyde (0.50 g, 0.0025 mol) in methanol (15 mL) was heated for 3 h to give a yellow precipitate. It was then filtered and washed with methanol to gives the pure schiff bases ( I). Colourless crystals of (I) are recrystallized from methanol. Yield: 68%; m. p. 206°C. IR (KBr) ν_max cm^-1: 2980 (C–H aromatic), 1642 (HC═N), 1607 (C═O), 1134 (C–N). ¹H-NMR (600 MHz, CDCl₃) d: 9.75 (CH═N, s), 7.49–7.29 (CH aromatic, m), 3.1(N–CH₃, s), 2.84 (N-CH₃, s), 2.15 (CH₃, s), 1.70 (CH₃, s).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound showing showing the molecules stacked along b- axis.

4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4- yl)methylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₃H₂₃N₅O	F(000) = 816
M_r = 385.46	D_x = 1.242 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3425 reflections
a = 15.2985 (2) Å	θ = 2.8–22.2°
b = 7.6827 (1) Å	µ = 0.08 mm⁻¹
c = 19.6737 (3) Å	T = 296 K
β = 116.905 (1)°	Block, colourless
V = 2062.03 (5) Å³	0.45 × 0.21 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5993 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
T_min = 0.965, T_max = 0.992	k = −10→10
23014 measured reflections	l = −27→27

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.0683P)² + 0.0093P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5993 reflections	Δρ_max = 0.24 e Å⁻³
311 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (13)

Crystal data top

C₂₃H₂₃N₅O	V = 2062.03 (5) Å³
M_r = 385.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2985 (2) Å	µ = 0.08 mm⁻¹
b = 7.6827 (1) Å	T = 296 K
c = 19.6737 (3) Å	0.45 × 0.21 × 0.10 mm
β = 116.905 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5993 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2881 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.992	R_int = 0.048
23014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
5993 reflections	Δρ_min = −0.18 e Å⁻³
311 parameters

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	0.11416 (10)	0.47531 (17)	0.60512 (9)	0.0735 (5)
N1	0.04112 (10)	0.21383 (18)	0.60925 (9)	0.0508 (4)
N2	0.07320 (10)	0.04036 (17)	0.62683 (9)	0.0474 (4)
N3	0.28754 (10)	0.22512 (19)	0.62644 (8)	0.0470 (4)
N4	0.57171 (10)	0.41293 (19)	0.66310 (9)	0.0509 (4)
N5	0.53154 (10)	0.55923 (17)	0.62050 (8)	0.0426 (4)
C1	−0.09125 (16)	0.4099 (3)	0.58937 (15)	0.0687 (6)
C2	−0.16074 (18)	0.4715 (4)	0.6111 (2)	0.0865 (9)
C3	−0.17010 (19)	0.3990 (4)	0.6710 (2)	0.0855 (8)
C4	−0.10854 (18)	0.2665 (3)	0.71182 (17)	0.0727 (7)
C5	−0.03755 (15)	0.2068 (3)	0.69323 (13)	0.0568 (5)
C6	−0.03009 (13)	0.2767 (2)	0.63100 (12)	0.0513 (5)
C7	0.11729 (13)	0.3159 (2)	0.60932 (10)	0.0491 (5)
C8	0.16367 (13)	0.0318 (2)	0.62798 (10)	0.0449 (4)
C9	0.19323 (12)	0.1939 (2)	0.61851 (9)	0.0428 (4)
C10	0.30947 (14)	0.3749 (2)	0.60912 (10)	0.0463 (4)
C11	0.40715 (12)	0.4167 (2)	0.62077 (9)	0.0410 (4)
C12	0.49667 (13)	0.3256 (2)	0.66248 (10)	0.0478 (5)
C13	0.43302 (12)	0.5662 (2)	0.59479 (9)	0.0409 (4)
C14	0.59465 (12)	0.6879 (2)	0.61384 (10)	0.0418 (4)
C15	0.66808 (15)	0.7576 (3)	0.67935 (12)	0.0586 (5)
C16	0.72986 (18)	0.8801 (3)	0.67306 (15)	0.0739 (7)
C17	0.71962 (16)	0.9330 (3)	0.60346 (14)	0.0670 (6)
C18	0.64705 (16)	0.8606 (3)	0.53863 (14)	0.0605 (6)
C19	0.58412 (15)	0.7374 (2)	0.54338 (11)	0.0508 (5)
C20	−0.00160 (14)	−0.0950 (2)	0.59196 (12)	0.0614 (5)
H20A	−0.0387	−0.0723	0.5384	0.092*
H20B	−0.0446	−0.0948	0.6154	0.092*
H20C	0.0296	−0.2066	0.5992	0.092*
C21	0.21737 (16)	−0.1350 (2)	0.64000 (15)	0.0748 (7)
H21A	0.2829	−0.1125	0.6477	0.112*
H21B	0.1844	−0.2079	0.5960	0.112*
H21C	0.2196	−0.1927	0.6840	0.112*
C22	0.51419 (15)	0.1564 (3)	0.70426 (13)	0.0727 (6)
H22A	0.5833	0.1332	0.7302	0.109*
H22B	0.4817	0.0645	0.6687	0.109*
H22C	0.4889	0.1629	0.7408	0.109*
C23	0.37292 (14)	0.7138 (3)	0.54809 (13)	0.0644 (6)
H23A	0.4032	0.8218	0.5715	0.097*
H23B	0.3084	0.7075	0.5448	0.097*
H23C	0.3684	0.7073	0.4979	0.097*
H1A	−0.0843 (13)	0.456 (2)	0.5486 (11)	0.055 (6)*
H2A	−0.1957 (19)	0.562 (4)	0.5826 (15)	0.106 (9)*
H3A	−0.2190 (17)	0.434 (3)	0.6873 (13)	0.088 (7)*
H4A	−0.1115 (17)	0.210 (3)	0.7549 (14)	0.091 (8)*
H5A	0.0095 (14)	0.115 (2)	0.7224 (11)	0.062 (6)*
H10A	0.2610 (12)	0.469 (2)	0.5891 (10)	0.052 (5)*
H15A	0.6715 (13)	0.724 (2)	0.7285 (11)	0.064 (6)*
H16A	0.7790 (17)	0.924 (3)	0.7169 (14)	0.092 (8)*
H17A	0.7596 (15)	1.023 (3)	0.5978 (12)	0.082 (7)*
H18A	0.6394 (13)	0.892 (2)	0.4898 (12)	0.067 (6)*
H19A	0.5326 (13)	0.682 (2)	0.4972 (11)	0.060 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0634 (9)	0.0410 (8)	0.1185 (13)	0.0000 (7)	0.0432 (9)	0.0135 (8)
N1	0.0454 (9)	0.0419 (8)	0.0686 (11)	−0.0020 (7)	0.0289 (8)	0.0045 (7)
N2	0.0494 (9)	0.0372 (8)	0.0616 (10)	−0.0071 (7)	0.0304 (8)	−0.0037 (7)
N3	0.0456 (9)	0.0494 (9)	0.0511 (9)	−0.0080 (7)	0.0263 (7)	−0.0023 (7)
N4	0.0458 (9)	0.0490 (9)	0.0560 (10)	−0.0008 (7)	0.0212 (7)	0.0111 (7)
N5	0.0415 (9)	0.0408 (8)	0.0467 (9)	−0.0013 (6)	0.0211 (7)	0.0051 (7)
C1	0.0535 (14)	0.0628 (14)	0.0775 (17)	0.0058 (11)	0.0188 (12)	0.0043 (12)
C2	0.0536 (15)	0.0703 (17)	0.113 (2)	0.0143 (13)	0.0180 (16)	−0.0166 (16)
C3	0.0572 (16)	0.093 (2)	0.109 (2)	−0.0042 (15)	0.0399 (16)	−0.0380 (18)
C4	0.0617 (15)	0.0759 (16)	0.0876 (18)	−0.0125 (13)	0.0400 (14)	−0.0276 (14)
C5	0.0496 (12)	0.0563 (12)	0.0661 (14)	−0.0056 (10)	0.0274 (11)	−0.0097 (11)
C6	0.0360 (10)	0.0458 (10)	0.0670 (13)	−0.0029 (8)	0.0189 (9)	−0.0075 (9)
C7	0.0427 (10)	0.0460 (10)	0.0557 (12)	−0.0055 (9)	0.0198 (9)	0.0049 (9)
C8	0.0464 (10)	0.0434 (10)	0.0523 (11)	−0.0062 (8)	0.0287 (9)	−0.0038 (8)
C9	0.0420 (10)	0.0455 (9)	0.0436 (10)	−0.0062 (8)	0.0216 (8)	−0.0023 (8)
C10	0.0465 (11)	0.0479 (10)	0.0465 (11)	−0.0042 (9)	0.0229 (9)	0.0013 (9)
C11	0.0428 (10)	0.0435 (9)	0.0420 (10)	−0.0061 (8)	0.0237 (8)	−0.0024 (8)
C12	0.0503 (11)	0.0479 (10)	0.0478 (11)	−0.0041 (9)	0.0243 (9)	0.0044 (8)
C13	0.0417 (10)	0.0425 (9)	0.0419 (10)	−0.0022 (7)	0.0218 (8)	−0.0005 (8)
C14	0.0415 (10)	0.0381 (9)	0.0508 (11)	−0.0025 (8)	0.0254 (9)	−0.0003 (8)
C15	0.0572 (12)	0.0649 (13)	0.0492 (13)	−0.0139 (10)	0.0200 (10)	0.0020 (10)
C16	0.0663 (15)	0.0719 (15)	0.0697 (17)	−0.0271 (12)	0.0187 (13)	−0.0036 (13)
C17	0.0657 (14)	0.0549 (12)	0.0818 (17)	−0.0181 (11)	0.0345 (13)	0.0019 (12)
C18	0.0769 (15)	0.0496 (11)	0.0662 (15)	−0.0079 (10)	0.0423 (13)	0.0047 (11)
C19	0.0615 (13)	0.0459 (10)	0.0501 (12)	−0.0115 (9)	0.0298 (10)	−0.0034 (9)
C20	0.0618 (13)	0.0536 (11)	0.0711 (14)	−0.0219 (10)	0.0322 (11)	−0.0095 (10)
C21	0.0783 (15)	0.0461 (12)	0.125 (2)	−0.0014 (11)	0.0680 (15)	−0.0048 (12)
C22	0.0644 (14)	0.0625 (13)	0.0870 (17)	0.0023 (11)	0.0306 (12)	0.0302 (12)
C23	0.0523 (12)	0.0575 (12)	0.0835 (15)	0.0062 (10)	0.0309 (11)	0.0151 (11)

Geometric parameters (Å, º) top

O1—C7	1.227 (2)	C11—C13	1.386 (2)
N1—C7	1.404 (2)	C11—C12	1.422 (2)
N1—N2	1.4082 (19)	C12—C22	1.496 (2)
N1—C6	1.423 (2)	C13—C23	1.487 (2)
N2—C8	1.375 (2)	C14—C19	1.375 (2)
N2—C20	1.467 (2)	C14—C15	1.378 (3)
N3—C10	1.287 (2)	C15—C16	1.379 (3)
N3—C9	1.400 (2)	C15—H15A	0.978 (19)
N4—C12	1.325 (2)	C16—C17	1.368 (3)
N4—N5	1.3702 (19)	C16—H16A	0.92 (2)
N5—C13	1.357 (2)	C17—C18	1.374 (3)
N5—C14	1.429 (2)	C17—H17A	0.96 (2)
C1—C6	1.378 (3)	C18—C19	1.383 (3)
C1—C2	1.396 (4)	C18—H18A	0.95 (2)
C1—H1A	0.927 (18)	C19—H19A	0.990 (19)
C2—C3	1.368 (4)	C20—H20A	0.9600
C2—H2A	0.90 (3)	C20—H20B	0.9600
C3—C4	1.372 (4)	C20—H20C	0.9600
C3—H3A	0.98 (2)	C21—H21A	0.9600
C4—C5	1.372 (3)	C21—H21B	0.9600
C4—H4A	0.97 (2)	C21—H21C	0.9600
C5—C6	1.388 (3)	C22—H22A	0.9600
C5—H5A	0.984 (19)	C22—H22B	0.9600
C7—C9	1.439 (2)	C22—H22C	0.9600
C8—C9	1.366 (2)	C23—H23A	0.9600
C8—C21	1.483 (2)	C23—H23B	0.9600
C10—C11	1.442 (2)	C23—H23C	0.9600
C10—H10A	0.982 (17)

C7—N1—N2	109.36 (13)	C11—C12—C22	129.15 (16)
C7—N1—C6	123.92 (15)	N5—C13—C11	106.51 (14)
N2—N1—C6	118.45 (14)	N5—C13—C23	122.19 (15)
C8—N2—N1	106.59 (13)	C11—C13—C23	131.30 (16)
C8—N2—C20	122.69 (15)	C19—C14—C15	120.63 (17)
N1—N2—C20	116.40 (14)	C19—C14—N5	120.55 (16)
C10—N3—C9	120.18 (15)	C15—C14—N5	118.79 (16)
C12—N4—N5	105.24 (14)	C14—C15—C16	118.9 (2)
C13—N5—N4	112.08 (13)	C14—C15—H15A	118.6 (11)
C13—N5—C14	128.42 (14)	C16—C15—H15A	122.4 (11)
N4—N5—C14	119.27 (13)	C17—C16—C15	121.4 (2)
C6—C1—C2	118.4 (3)	C17—C16—H16A	120.3 (15)
C6—C1—H1A	119.1 (12)	C15—C16—H16A	118.3 (15)
C2—C1—H1A	122.5 (12)	C16—C17—C18	119.2 (2)
C3—C2—C1	121.1 (3)	C16—C17—H17A	122.6 (13)
C3—C2—H2A	125.9 (17)	C18—C17—H17A	118.2 (13)
C1—C2—H2A	113.0 (18)	C17—C18—C19	120.6 (2)
C2—C3—C4	119.6 (3)	C17—C18—H18A	121.0 (12)
C2—C3—H3A	124.3 (14)	C19—C18—H18A	118.4 (12)
C4—C3—H3A	116.1 (14)	C14—C19—C18	119.34 (19)
C5—C4—C3	120.6 (3)	C14—C19—H19A	119.2 (10)
C5—C4—H4A	115.9 (14)	C18—C19—H19A	121.5 (10)
C3—C4—H4A	123.5 (14)	N2—C20—H20A	109.5
C4—C5—C6	119.8 (2)	N2—C20—H20B	109.5
C4—C5—H5A	122.7 (11)	H20A—C20—H20B	109.5
C6—C5—H5A	117.5 (11)	N2—C20—H20C	109.5
C1—C6—C5	120.4 (2)	H20A—C20—H20C	109.5
C1—C6—N1	118.7 (2)	H20B—C20—H20C	109.5
C5—C6—N1	120.90 (17)	C8—C21—H21A	109.5
O1—C7—N1	123.40 (17)	C8—C21—H21B	109.5
O1—C7—C9	131.56 (17)	H21A—C21—H21B	109.5
N1—C7—C9	104.99 (14)	C8—C21—H21C	109.5
C9—C8—N2	110.30 (15)	H21A—C21—H21C	109.5
C9—C8—C21	128.03 (16)	H21B—C21—H21C	109.5
N2—C8—C21	121.65 (15)	C12—C22—H22A	109.5
C8—C9—N3	121.95 (15)	C12—C22—H22B	109.5
C8—C9—C7	108.22 (15)	H22A—C22—H22B	109.5
N3—C9—C7	129.41 (15)	C12—C22—H22C	109.5
N3—C10—C11	122.19 (18)	H22A—C22—H22C	109.5
N3—C10—H10A	121.7 (10)	H22B—C22—H22C	109.5
C11—C10—H10A	116.1 (10)	C13—C23—H23A	109.5
C13—C11—C12	105.06 (14)	C13—C23—H23B	109.5
C13—C11—C10	125.06 (16)	H23A—C23—H23B	109.5
C12—C11—C10	129.81 (16)	C13—C23—H23C	109.5
N4—C12—C11	111.10 (15)	H23A—C23—H23C	109.5
N4—C12—C22	119.73 (16)	H23B—C23—H23C	109.5

C7—N1—N2—C8	−7.52 (18)	N1—C7—C9—C8	−3.59 (19)
C6—N1—N2—C8	−157.20 (15)	O1—C7—C9—N3	1.0 (3)
C7—N1—N2—C20	−148.51 (16)	N1—C7—C9—N3	−176.21 (16)
C6—N1—N2—C20	61.8 (2)	C9—N3—C10—C11	176.07 (15)
C12—N4—N5—C13	1.35 (18)	N3—C10—C11—C13	171.42 (16)
C12—N4—N5—C14	176.16 (14)	N3—C10—C11—C12	−12.0 (3)
C6—C1—C2—C3	−1.7 (4)	N5—N4—C12—C11	−1.32 (19)
C1—C2—C3—C4	1.7 (4)	N5—N4—C12—C22	−179.90 (16)
C2—C3—C4—C5	0.3 (4)	C13—C11—C12—N4	0.84 (19)
C3—C4—C5—C6	−2.3 (3)	C10—C11—C12—N4	−176.23 (17)
C2—C1—C6—C5	−0.3 (3)	C13—C11—C12—C22	179.26 (19)
C2—C1—C6—N1	−179.76 (19)	C10—C11—C12—C22	2.2 (3)
C4—C5—C6—C1	2.3 (3)	N4—N5—C13—C11	−0.84 (18)
C4—C5—C6—N1	−178.27 (17)	C14—N5—C13—C11	−175.06 (15)
C7—N1—C6—C1	62.0 (2)	N4—N5—C13—C23	179.18 (16)
N2—N1—C6—C1	−153.01 (17)	C14—N5—C13—C23	5.0 (3)
C7—N1—C6—C5	−117.4 (2)	C12—C11—C13—N5	0.01 (17)
N2—N1—C6—C5	27.5 (2)	C10—C11—C13—N5	177.27 (15)
N2—N1—C7—O1	−170.72 (18)	C12—C11—C13—C23	179.99 (19)
C6—N1—C7—O1	−23.1 (3)	C10—C11—C13—C23	−2.8 (3)
N2—N1—C7—C9	6.80 (18)	C13—N5—C14—C19	−63.0 (2)
C6—N1—C7—C9	154.47 (17)	N4—N5—C14—C19	123.15 (18)
N1—N2—C8—C9	5.20 (19)	C13—N5—C14—C15	118.9 (2)
C20—N2—C8—C9	143.14 (17)	N4—N5—C14—C15	−55.0 (2)
N1—N2—C8—C21	−176.14 (18)	C19—C14—C15—C16	1.1 (3)
C20—N2—C8—C21	−38.2 (3)	N5—C14—C15—C16	179.18 (18)
N2—C8—C9—N3	172.28 (14)	C14—C15—C16—C17	−0.1 (3)
C21—C8—C9—N3	−6.3 (3)	C15—C16—C17—C18	−0.9 (4)
N2—C8—C9—C7	−1.0 (2)	C16—C17—C18—C19	0.9 (3)
C21—C8—C9—C7	−179.6 (2)	C15—C14—C19—C18	−1.1 (3)
C10—N3—C9—C8	172.48 (17)	N5—C14—C19—C18	−179.16 (16)
C10—N3—C9—C7	−15.8 (3)	C17—C18—C19—C14	0.1 (3)
O1—C7—C9—C8	173.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N4/N5/C11–C13 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.986 (18)	2.40 (2)	3.052 (3)	123.3 (14)
C19—H19A···Cg2ⁱ	0.990 (19)	2.656 (19)	3.452 (2)	137.4 (17)
C20—H20C···Cg1ⁱⁱ	0.96	2.85 (3)	3.720 (3)	149 (1)
C22—H22B···Cg2ⁱⁱⁱ	0.96	2.82 (3)	3.585 (3)	135 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃N₅O
M_r	385.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.2985 (2), 7.6827 (1), 19.6737 (3)
β (°)	116.905 (1)
V (Å³)	2062.03 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.965, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	23014, 5993, 2881
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.161, 1.03
No. of reflections	5993
No. of parameters	311
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N4/N5/C11–C13 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.986 (18)	2.40 (2)	3.052 (3)	123.3 (14)
C19—H19A···Cg2ⁱ	0.990 (19)	2.656 (19)	3.452 (2)	137.4 (17)
C20—H20C···Cg1ⁱⁱ	0.96	2.85 (3)	3.720 (3)	149.0 (2)
C22—H22B···Cg2ⁱⁱⁱ	0.96	2.82 (3)	3.585 (3)	135.0 (2)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§On secondment to: The Center of Excellence for Advanced Materials Research, King Abdu Aziz University, Jeddah 21589, Saudi Arabia.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks USM for a post-doctoral research fellowship. AMA and SAK thank the Chemistry Department, King Abdul Aziz University, Jeddah, for providing research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eryigit, R. & Kendi, E. (1998). J. Chem. Crystallogr. 28, 145–147. Web of Science CSD CrossRef CAS Google Scholar
Geronikaki, J. M. A., Litina, D. H. & Amourgianou, M. (2003). Farmaco, 58, 489–495. CrossRef PubMed CAS Google Scholar
Li, X., Schofield, B. H., Huang, C., Kleiner, G. I., Hugh, A. & Sampson, H. A. (1999). J. Allergy Clin. Immunol. 103, 206–214. Web of Science CrossRef CAS PubMed Google Scholar
Manikandan, P., Justin Thomas, K. R. & Manoharan, P. T. (2000). Acta Cryst. C56, 308–309. CSD CrossRef CAS IUCr Journals Google Scholar
Nawaz, H., Akhter, Z., Yameen, S., Siddiqi, H. M., Mirza, B. & Rifat, A. (2009). J. Organomet. Chem. 694, 2198–2203. Web of Science CrossRef CAS Google Scholar
Nawrocka, W., Sztuba, B., Kowalska, M. W., Liszkiewicz, H., Wietrzyk, J., Nasulewicz, A., Peczyska, M. & Opolski, A. (2004). Il Farmaco, 59, 83–91. CrossRef PubMed CAS Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. D. (1999). Pharm. Acta Helv. 74, 11–17. CrossRef PubMed CAS Google Scholar
Shanker, K., Rohini, R., Ravinder, V., Reddy, P. M. & Ho, Y. (2009). Spectrochim. Acta Part A, 73, 205–211. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129–132. Web of Science CrossRef PubMed CAS Google Scholar
Urena, F. H., Illn-Cabeza, N. A., Moreno-Carretero, M. N. & José, M. (2003). J. Inorg. Biochem. 94, 326–334. Web of Science PubMed Google Scholar

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Volume 66| Part 7| July 2010| Pages o1602-o1603

doi:10.1107/S1600536810021173

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

4-{[(E)-(3,5-Di­methyl-1-phenyl-1H-pyrazol-4-yl)methyl­­idene]amino}-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one