1,5-Dimethyl-4-{[1-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)eth­yl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Zhu, H.; Shi, J.; Wei, Z.; Bai, Y.; Bu, L.

doi:10.1107/S1600536810020532

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1583

doi:10.1107/S1600536810020532

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1,5-Dimethyl-4-{[1-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)ethyl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Hualing Zhu,^a ^* Jun Shi,^a Zhen Wei,^a Yanan Bai ^a and Luxia Bu ^a

^aDepartment of Basic Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China
^*Correspondence e-mail: zhuhualing2004@126.com

(Received 25 May 2010; accepted 30 May 2010; online 5 June 2010)

In the title compound, C₂₃H₂₃N₅O₂, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring, and the dihedral angle between the pyrazole rings is 48.42 (8)°. The dihedral angles between the pyrazole rings and their attached phenyl rings are 10.06 (8) and 47.53 (8)°.

Related literature

For related structures and background references, see: Zhang et al. (2010 ); Zhu et al. (2010 ).

Experimental

Crystal data

C₂₃H₂₃N₅O₂
M_r = 401.46
Monoclinic, C 2/c
a = 20.486 (4) Å
b = 10.209 (2) Å
c = 19.753 (4) Å
β = 102.76 (3)°
V = 4029.3 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.983, T_max = 0.990
13299 measured reflections
3553 independent reflections
2858 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.00
3553 reflections
280 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.90 (1)	1.85 (1)	2.6459 (15)	146 (2)

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020532/hb5465sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020532/hb5465Isup2.hkl

checkCIF report

Comment top

As part of our onging studies of pyrazole derivatives (Zhu et al., 2010), we now report the structure of the title compound, (I).

In the molecule of the title compound, (Fig.1) there is one molecule in the asymmetric unit. Atom O1, C7, C8, C11 and atom N3 form a plane, the largest deviation being 0.0132 (15) Å for atom C11. The dihedral angle between this plane and the pyrazolone ring of PMAP is 0.46 (4)°, indicating that they are essentially coplanar, as seen in Ethyl 2–{[(1Z)–(3– methyl–5–oxo–1–phenyl–4,5–dihydro–1H–pyrazol–4–ylidene) (p–tolyl)methyl]amino}–3–phenylpropanoate (1.52 (4)°; Zhang et al., 2010). The bond lengths within this part of the molecular lie between classical single–and double–bond lengths, indicating extensive conjugation. Atoms N5,N4, C14, C13,C17 and O2 are also nearly coplanar, the largest deviation being 0.0417 (15) Å for atom C14.The dihedral angle between this plane and the phenyl ring of antipyrine is 47.41 (5)°, A strong intramolecular hydrogen bond N3—H3···O1 is observed (Table 1 & Fig. 1), stabilizing to an enamine–keto form.

Related literature top

For related structures and background references, see: Zhang et al. (2010); Zhu et al. (2010).

Experimental top

A mixture of HPMAP (15m mol) and 4-antipyrine (15m mol) in ethanol (100 ml) was refluxed over a steam bath for about 4 h, then the solution was cooled down to room temperature. After one day, pale yellow blocks were obtained and dried in air. The product was recrystallized from ethanol which afforded pale yellow blocks of (I).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as spheres of arbitrary radius.

1,5-Dimethyl-4-{[1-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4- ylidene)ethyl]amino}-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₃H₂₃N₅O₂	F(000) = 1696
M_r = 401.46	D_x = 1.324 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5835 reflections
a = 20.486 (4) Å	θ = 2.0–27.9°
b = 10.209 (2) Å	µ = 0.09 mm⁻¹
c = 19.753 (4) Å	T = 113 K
β = 102.76 (3)°	Block, pale yellow
V = 4029.3 (14) Å³	0.20 × 0.18 × 0.12 mm
Z = 8

Data collection top

Rigaku Saturn CCD diffractometer	3553 independent reflections
Radiation source: rotating anode	2858 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.038
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω and ϕ scans	h = −24→21
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→12
T_min = 0.983, T_max = 0.990	l = −23→20
13299 measured reflections

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0698P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3553 reflections	Δρ_max = 0.24 e Å⁻³
280 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (7)

Crystal data top

C₂₃H₂₃N₅O₂	V = 4029.3 (14) Å³
M_r = 401.46	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.486 (4) Å	µ = 0.09 mm⁻¹
b = 10.209 (2) Å	T = 113 K
c = 19.753 (4) Å	0.20 × 0.18 × 0.12 mm
β = 102.76 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	3553 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2858 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.990	R_int = 0.038
13299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.24 e Å⁻³
3553 reflections	Δρ_min = −0.20 e Å⁻³
280 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	0.36779 (5)	0.46740 (9)	−0.06459 (5)	0.0331 (3)
O2	0.30384 (5)	0.76857 (9)	0.14645 (5)	0.0320 (3)
N1	0.48756 (6)	0.27136 (11)	0.04420 (6)	0.0290 (3)
N2	0.44223 (6)	0.29879 (11)	−0.01884 (6)	0.0258 (3)
N3	0.36650 (6)	0.64889 (11)	0.03072 (6)	0.0275 (3)
N4	0.31259 (6)	0.98296 (10)	0.01180 (6)	0.0265 (3)
N5	0.29411 (6)	0.95272 (11)	0.07449 (6)	0.0267 (3)
C1	0.44049 (7)	0.21464 (12)	−0.07603 (7)	0.0250 (3)
C2	0.39265 (7)	0.23181 (13)	−0.13788 (7)	0.0302 (4)
H2	0.3599	0.2988	−0.1414	0.036*
C3	0.39318 (8)	0.15100 (13)	−0.19403 (8)	0.0340 (4)
H3	0.3608	0.1633	−0.2361	0.041*
C4	0.44038 (8)	0.05234 (14)	−0.18963 (8)	0.0334 (4)
H4	0.4408	−0.0021	−0.2285	0.040*
C5	0.48688 (8)	0.03395 (13)	−0.12788 (8)	0.0325 (4)
H5	0.5188	−0.0346	−0.1243	0.039*
C6	0.48738 (7)	0.11448 (13)	−0.07107 (8)	0.0284 (3)
H6	0.5196	0.1012	−0.0290	0.034*
C7	0.40969 (7)	0.41613 (13)	−0.01570 (7)	0.0252 (3)
C8	0.43465 (7)	0.46416 (12)	0.05373 (7)	0.0246 (3)
C9	0.48298 (7)	0.36845 (13)	0.08621 (7)	0.0265 (3)
C10	0.52713 (8)	0.36606 (15)	0.15746 (8)	0.0383 (4)
H10A	0.5499	0.2812	0.1655	0.057*
H10B	0.4999	0.3793	0.1919	0.057*
H10C	0.5605	0.4361	0.1617	0.057*
C11	0.41305 (7)	0.58307 (13)	0.07650 (7)	0.0242 (3)
C12	0.43823 (8)	0.63774 (13)	0.14760 (7)	0.0296 (4)
H12A	0.4385	0.7336	0.1453	0.044*
H12B	0.4838	0.6061	0.1663	0.044*
H12C	0.4089	0.6094	0.1779	0.044*
C13	0.34091 (7)	0.77511 (12)	0.03765 (7)	0.0236 (3)
C14	0.33636 (7)	0.87041 (12)	−0.01143 (7)	0.0238 (3)
C15	0.35030 (8)	0.86237 (14)	−0.08178 (7)	0.0302 (4)
H15A	0.3841	0.7946	−0.0824	0.045*
H15B	0.3670	0.9471	−0.0940	0.045*
H15C	0.3090	0.8401	−0.1155	0.045*
C16	0.26801 (8)	1.07262 (14)	−0.03498 (8)	0.0340 (4)
H16A	0.2931	1.1167	−0.0653	0.051*
H16B	0.2502	1.1381	−0.0076	0.051*
H16C	0.2309	1.0229	−0.0634	0.051*
C17	0.31227 (7)	0.82187 (13)	0.09295 (7)	0.0252 (3)
C18	0.29907 (7)	1.05520 (13)	0.12492 (7)	0.0268 (3)
C19	0.26278 (7)	1.04378 (15)	0.17587 (7)	0.0325 (4)
H19	0.2345	0.9703	0.1765	0.039*
C20	0.26814 (8)	1.14062 (16)	0.22600 (8)	0.0412 (4)
H20	0.2439	1.1326	0.2616	0.049*
C21	0.30837 (9)	1.24844 (17)	0.22456 (9)	0.0454 (5)
H21	0.3116	1.3147	0.2589	0.054*
C22	0.34389 (9)	1.25982 (15)	0.17310 (9)	0.0429 (4)
H22	0.3712	1.3345	0.1718	0.052*
C23	0.33989 (8)	1.16264 (13)	0.12312 (8)	0.0344 (4)
H23	0.3649	1.1698	0.0881	0.041*
H3A	0.3562 (8)	0.6116 (14)	−0.0115 (6)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0351 (6)	0.0329 (5)	0.0257 (6)	0.0095 (5)	−0.0053 (5)	−0.0022 (4)
O2	0.0367 (6)	0.0363 (6)	0.0236 (6)	−0.0021 (5)	0.0081 (5)	0.0049 (5)
N1	0.0286 (7)	0.0338 (7)	0.0217 (7)	0.0052 (5)	−0.0003 (5)	0.0042 (5)
N2	0.0265 (7)	0.0284 (6)	0.0198 (6)	0.0039 (5)	−0.0006 (5)	0.0006 (5)
N3	0.0322 (7)	0.0267 (6)	0.0216 (6)	0.0026 (5)	0.0016 (6)	−0.0033 (5)
N4	0.0322 (7)	0.0294 (6)	0.0186 (6)	0.0050 (5)	0.0073 (5)	0.0030 (5)
N5	0.0322 (7)	0.0296 (6)	0.0198 (6)	0.0045 (5)	0.0092 (5)	0.0016 (5)
C1	0.0270 (8)	0.0253 (7)	0.0230 (8)	−0.0017 (6)	0.0063 (6)	0.0005 (6)
C2	0.0311 (9)	0.0308 (7)	0.0264 (8)	0.0043 (6)	0.0011 (7)	0.0012 (6)
C3	0.0401 (9)	0.0357 (8)	0.0236 (8)	0.0003 (7)	0.0012 (7)	−0.0004 (6)
C4	0.0404 (10)	0.0324 (8)	0.0296 (9)	−0.0027 (7)	0.0126 (7)	−0.0045 (7)
C5	0.0318 (9)	0.0279 (7)	0.0398 (9)	0.0030 (6)	0.0123 (7)	−0.0008 (7)
C6	0.0271 (8)	0.0280 (7)	0.0291 (8)	0.0001 (6)	0.0038 (6)	0.0032 (6)
C7	0.0234 (8)	0.0276 (7)	0.0232 (8)	0.0020 (6)	0.0019 (6)	0.0021 (6)
C8	0.0240 (8)	0.0281 (7)	0.0207 (8)	−0.0008 (6)	0.0027 (6)	0.0025 (6)
C9	0.0261 (8)	0.0310 (7)	0.0223 (7)	0.0017 (6)	0.0049 (6)	0.0035 (6)
C10	0.0404 (10)	0.0485 (9)	0.0226 (8)	0.0144 (8)	−0.0001 (7)	0.0007 (7)
C11	0.0236 (8)	0.0271 (7)	0.0213 (7)	−0.0031 (6)	0.0035 (6)	0.0035 (6)
C12	0.0313 (8)	0.0320 (8)	0.0233 (8)	0.0014 (6)	0.0015 (6)	−0.0008 (6)
C13	0.0239 (7)	0.0248 (7)	0.0209 (7)	−0.0005 (6)	0.0023 (6)	−0.0013 (6)
C14	0.0207 (7)	0.0298 (7)	0.0200 (7)	0.0001 (6)	0.0025 (6)	−0.0027 (6)
C15	0.0316 (9)	0.0378 (8)	0.0213 (8)	0.0026 (7)	0.0061 (6)	0.0007 (6)
C16	0.0387 (9)	0.0323 (8)	0.0308 (9)	0.0100 (7)	0.0073 (7)	0.0076 (7)
C17	0.0237 (8)	0.0294 (7)	0.0207 (7)	−0.0022 (6)	0.0009 (6)	0.0006 (6)
C18	0.0266 (8)	0.0315 (7)	0.0205 (7)	0.0087 (6)	0.0015 (6)	−0.0018 (6)
C19	0.0276 (8)	0.0443 (9)	0.0244 (8)	0.0095 (7)	0.0030 (6)	−0.0002 (7)
C20	0.0355 (10)	0.0633 (11)	0.0232 (8)	0.0165 (8)	0.0029 (7)	−0.0056 (8)
C21	0.0475 (11)	0.0484 (10)	0.0339 (10)	0.0148 (8)	−0.0048 (8)	−0.0161 (8)
C22	0.0455 (11)	0.0378 (9)	0.0407 (10)	0.0037 (8)	−0.0009 (8)	−0.0095 (8)
C23	0.0340 (9)	0.0354 (8)	0.0328 (9)	0.0044 (7)	0.0052 (7)	−0.0015 (7)

Geometric parameters (Å, º) top

O1—C7	1.2559 (17)	C9—C10	1.496 (2)
O2—C17	1.2341 (16)	C10—H10A	0.9800
N1—C9	1.3093 (18)	C10—H10B	0.9800
N1—N2	1.4073 (16)	C10—H10C	0.9800
N2—C7	1.3792 (17)	C11—C12	1.4933 (19)
N2—C1	1.4133 (17)	C12—H12A	0.9800
N3—C11	1.3408 (18)	C12—H12B	0.9800
N3—C13	1.4091 (17)	C12—H12C	0.9800
N3—H3A	0.899 (9)	C13—C14	1.3622 (19)
N4—C14	1.3664 (16)	C13—C17	1.4314 (19)
N4—N5	1.4068 (16)	C14—C15	1.4814 (19)
N4—C16	1.4673 (18)	C15—H15A	0.9800
N5—C17	1.4128 (17)	C15—H15B	0.9800
N5—C18	1.4327 (17)	C15—H15C	0.9800
C1—C6	1.391 (2)	C16—H16A	0.9800
C1—C2	1.398 (2)	C16—H16B	0.9800
C2—C3	1.384 (2)	C16—H16C	0.9800
C2—H2	0.9500	C18—C19	1.382 (2)
C3—C4	1.386 (2)	C18—C23	1.385 (2)
C3—H3	0.9500	C19—C20	1.386 (2)
C4—C5	1.385 (2)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.379 (3)
C5—C6	1.3893 (19)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.379 (3)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.4396 (19)	C22—C23	1.389 (2)
C8—C11	1.4000 (19)	C22—H22	0.9500
C8—C9	1.4373 (19)	C23—H23	0.9500

C9—N1—N2	106.53 (11)	N3—C11—C12	119.56 (12)
C7—N2—N1	111.35 (10)	C8—C11—C12	123.93 (12)
C7—N2—C1	129.57 (11)	C11—C12—H12A	109.5
N1—N2—C1	118.78 (11)	C11—C12—H12B	109.5
C11—N3—C13	128.11 (12)	H12A—C12—H12B	109.5
C11—N3—H3A	113.6 (11)	C11—C12—H12C	109.5
C13—N3—H3A	117.5 (11)	H12A—C12—H12C	109.5
C14—N4—N5	107.23 (10)	H12B—C12—H12C	109.5
C14—N4—C16	122.11 (12)	C14—C13—N3	123.54 (13)
N5—N4—C16	116.12 (11)	C14—C13—C17	109.25 (12)
N4—N5—C17	109.15 (10)	N3—C13—C17	127.10 (12)
N4—N5—C18	117.40 (11)	C13—C14—N4	109.58 (12)
C17—N5—C18	122.47 (11)	C13—C14—C15	129.12 (12)
C6—C1—C2	119.56 (13)	N4—C14—C15	121.23 (12)
C6—C1—N2	119.69 (13)	C14—C15—H15A	109.5
C2—C1—N2	120.74 (12)	C14—C15—H15B	109.5
C3—C2—C1	119.82 (13)	H15A—C15—H15B	109.5
C3—C2—H2	120.1	C14—C15—H15C	109.5
C1—C2—H2	120.1	H15A—C15—H15C	109.5
C2—C3—C4	120.79 (14)	H15B—C15—H15C	109.5
C2—C3—H3	119.6	N4—C16—H16A	109.5
C4—C3—H3	119.6	N4—C16—H16B	109.5
C5—C4—C3	119.24 (14)	H16A—C16—H16B	109.5
C5—C4—H4	120.4	N4—C16—H16C	109.5
C3—C4—H4	120.4	H16A—C16—H16C	109.5
C4—C5—C6	120.81 (13)	H16B—C16—H16C	109.5
C4—C5—H5	119.6	O2—C17—N5	124.01 (13)
C6—C5—H5	119.6	O2—C17—C13	131.67 (13)
C5—C6—C1	119.75 (14)	N5—C17—C13	104.32 (11)
C5—C6—H6	120.1	C19—C18—C23	120.71 (13)
C1—C6—H6	120.1	C19—C18—N5	118.54 (13)
O1—C7—N2	125.62 (12)	C23—C18—N5	120.74 (13)
O1—C7—C8	128.99 (13)	C18—C19—C20	119.31 (15)
N2—C7—C8	105.38 (11)	C18—C19—H19	120.3
C11—C8—C9	132.97 (13)	C20—C19—H19	120.3
C11—C8—C7	122.03 (12)	C21—C20—C19	120.52 (16)
C9—C8—C7	104.97 (12)	C21—C20—H20	119.7
N1—C9—C8	111.75 (12)	C19—C20—H20	119.7
N1—C9—C10	118.09 (12)	C20—C21—C22	119.82 (15)
C8—C9—C10	130.15 (13)	C20—C21—H21	120.1
C9—C10—H10A	109.5	C22—C21—H21	120.1
C9—C10—H10B	109.5	C21—C22—C23	120.38 (16)
H10A—C10—H10B	109.5	C21—C22—H22	119.8
C9—C10—H10C	109.5	C23—C22—H22	119.8
H10A—C10—H10C	109.5	C18—C23—C22	119.25 (15)
H10B—C10—H10C	109.5	C18—C23—H23	120.4
N3—C11—C8	116.50 (12)	C22—C23—H23	120.4

C9—N1—N2—C7	0.73 (15)	C9—C8—C11—N3	179.24 (14)
C9—N1—N2—C1	175.01 (12)	C7—C8—C11—N3	1.6 (2)
C14—N4—N5—C17	5.07 (15)	C9—C8—C11—C12	−1.4 (2)
C16—N4—N5—C17	145.59 (12)	C7—C8—C11—C12	−179.06 (13)
C14—N4—N5—C18	150.16 (12)	C11—N3—C13—C14	130.25 (16)
C16—N4—N5—C18	−69.32 (15)	C11—N3—C13—C17	−53.9 (2)
C7—N2—C1—C6	167.10 (13)	N3—C13—C14—N4	−177.17 (12)
N1—N2—C1—C6	−5.98 (19)	C17—C13—C14—N4	6.37 (16)
C7—N2—C1—C2	−12.1 (2)	N3—C13—C14—C15	5.8 (2)
N1—N2—C1—C2	174.78 (12)	C17—C13—C14—C15	−170.70 (13)
C6—C1—C2—C3	−1.4 (2)	N5—N4—C14—C13	−7.03 (15)
N2—C1—C2—C3	177.88 (13)	C16—N4—C14—C13	−144.66 (13)
C1—C2—C3—C4	0.4 (2)	N5—N4—C14—C15	170.30 (12)
C2—C3—C4—C5	0.8 (2)	C16—N4—C14—C15	32.7 (2)
C3—C4—C5—C6	−1.1 (2)	N4—N5—C17—O2	178.14 (12)
C4—C5—C6—C1	0.2 (2)	C18—N5—C17—O2	35.2 (2)
C2—C1—C6—C5	1.0 (2)	N4—N5—C17—C13	−1.27 (14)
N2—C1—C6—C5	−178.23 (12)	C18—N5—C17—C13	−144.24 (13)
N1—N2—C7—O1	178.08 (13)	C14—C13—C17—O2	177.62 (14)
C1—N2—C7—O1	4.6 (2)	N3—C13—C17—O2	1.3 (2)
N1—N2—C7—C8	−1.39 (15)	C14—C13—C17—N5	−3.03 (15)
C1—N2—C7—C8	−174.88 (13)	N3—C13—C17—N5	−179.33 (13)
O1—C7—C8—C11	0.3 (2)	N4—N5—C18—C19	159.88 (12)
N2—C7—C8—C11	179.69 (12)	C17—N5—C18—C19	−59.97 (18)
O1—C7—C8—C9	−177.98 (14)	N4—N5—C18—C23	−20.81 (19)
N2—C7—C8—C9	1.45 (15)	C17—N5—C18—C23	119.34 (15)
N2—N1—C9—C8	0.27 (16)	C23—C18—C19—C20	−0.7 (2)
N2—N1—C9—C10	−178.89 (13)	N5—C18—C19—C20	178.58 (13)
C11—C8—C9—N1	−179.06 (14)	C18—C19—C20—C21	1.1 (2)
C7—C8—C9—N1	−1.10 (16)	C19—C20—C21—C22	−0.4 (2)
C11—C8—C9—C10	0.0 (3)	C20—C21—C22—C23	−0.7 (2)
C7—C8—C9—C10	177.93 (15)	C19—C18—C23—C22	−0.3 (2)
C13—N3—C11—C8	−173.48 (13)	N5—C18—C23—C22	−179.56 (13)
C13—N3—C11—C12	7.1 (2)	C21—C22—C23—C18	1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.90 (1)	1.85 (1)	2.6459 (15)	146 (2)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃N₅O₂
M_r	401.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	20.486 (4), 10.209 (2), 19.753 (4)
β (°)	102.76 (3)
V (Å³)	4029.3 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.983, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13299, 3553, 2858
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.00
No. of reflections	3553
No. of parameters	280
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.899 (9)	1.853 (12)	2.6459 (15)	145.9 (15)

Acknowledgements

The authors thank the Science Development Committee of Tianjin Agricultural College for partial funding (research grant No. 2007029).

References

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X., Huang, M., Du, C. & Han, J. (2010). Acta Cryst. E66, o273. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Shi, J., Wei, Z., Dai, R. & Zhang, X. (2010). Acta Cryst. E66, o1352. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1583

doi:10.1107/S1600536810020532

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

1,5-Di­methyl-4-{[1-(3-methyl-5-oxo-1-phenyl-4,5-di­hydro-1H-pyrazol-4-yl­­idene)eth­yl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Dimethyl-4-{[1-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)ethyl]amino}-2-phenyl-1H-pyrazol-3(2H)-one