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

In the title compound, C(23)H(23)N(5)O(2), an intra-molecular 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 = 401.46

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.00

3553 reflections

280 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

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

C23H23N5O2	F(000) = 1696
Mr = 401.46	Dx = 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

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

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(Fo2) + (0.0698P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3553 reflections	Δρmax = 0.24 e Å−3
280 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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)