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

The title Schiff base compound, C(23)H(23)N(5)O, was synthesized by the reaction of 4-amino-phenazone and 3,5-dimethyl-1-phenyl-pyrazole-4-carbaxaldehyde. The mol-ecule adopts an E configuration about the central C=N double bond. A weak intra-molecular 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 inter-actions 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 = 385.46

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.161

S = 1.03

5993 reflections

311 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021173/lh5060sup1.cif

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

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

C23H23N5O	F(000) = 816
Mr = 385.46	Dx = 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

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

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(Fo2) + (0.0683P)2 + 0.0093P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5993 reflections	Δρmax = 0.24 e Å−3
311 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .