(4Z)-4-[(Cyclo-propyl-amino)(phen-yl)methyl-ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the title compound, C(20)H(19)N(3)O, the dihedral angles formed by the pyrazolone ring with the two phenyl rings are 64.27 (6) and 17.00 (6)°. The mol-ecular structure is stabilized by intra-molecular N-H⋯O and C-H⋯O hydrogen bonds. In the crystal, the mol-ecules are linked into chains along the b axis by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the anti­bacterial, biological and analgesic activity of metal complexes of 1-phenyl-3-methyl-4-benzoyl­pyrazolon-5-one, see: Li et al. (1997 ▶); Liu et al. (1980 ▶); Zhou et al. (1999 ▶). For a related structure, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C20H19N3O

M = 317.38

Orthorhombic,

a = 8.9790 (18) Å

b = 18.500 (4) Å

c = 20.050 (4) Å

V = 3330.5 (12) Å3

Z = 8

Cu Kα radiation

μ = 0.63 mm−1

T = 113 K

0.24 × 0.21 × 0.20 mm

Data collection

Rigaku Saturn70 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.863, T max = 0.884

34928 measured reflections

3262 independent reflections

2946 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.06

3262 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.24 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: CrystalStructure (Rigaku, 2005 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013723/ci5077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013723/ci5077Isup2.hkl

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

C20H19N3O	F(000) = 1344
Mr = 317.38	Dx = 1.266 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2126 reflections
a = 8.9790 (18) Å	θ = 2.2–45.5°
b = 18.500 (4) Å	µ = 0.63 mm−1
c = 20.050 (4) Å	T = 113 K
V = 3330.5 (12) Å3	Prism, colourless
Z = 8	0.24 × 0.21 × 0.20 mm

Rigaku Saturn70 diffractometer	3262 independent reflections
Radiation source: fine-focus sealed tube	2946 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω scans	θmax = 72.5°, θmin = 4.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −8→10
Tmin = 0.863, Tmax = 0.884	k = −22→22
34928 measured reflections	l = −24→24

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.7718P] where P = (Fo2 + 2Fc2)/3
3262 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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	0.67690 (13)	0.11712 (5)	0.26555 (4)	0.0415 (3)
N1	0.73850 (11)	0.08273 (5)	0.15606 (5)	0.0274 (2)
N2	0.82349 (11)	0.02871 (5)	0.12501 (5)	0.0262 (2)
N3	0.79592 (14)	0.02403 (5)	0.35244 (5)	0.0336 (3)
C1	0.73711 (15)	0.07497 (6)	0.22477 (6)	0.0299 (3)
C2	0.82015 (14)	0.00961 (6)	0.23704 (5)	0.0266 (3)
C3	0.87030 (13)	−0.01421 (6)	0.17276 (5)	0.0248 (2)
C4	0.96427 (14)	−0.07788 (7)	0.15470 (6)	0.0313 (3)
H4A	0.9070	−0.1224	0.1613	0.038*
H4B	1.0531	−0.0789	0.1831	0.038*
H4C	0.9944	−0.0742	0.1079	0.038*
C5	0.84118 (13)	−0.01694 (6)	0.30210 (5)	0.0260 (3)
C6	0.90512 (12)	−0.08952 (6)	0.31601 (5)	0.0246 (2)
C7	1.03261 (14)	−0.09759 (8)	0.35553 (6)	0.0344 (3)
H7	1.0806	−0.0562	0.3736	0.041*
C8	1.08875 (16)	−0.16611 (9)	0.36826 (7)	0.0454 (4)
H8	1.1754	−0.1715	0.3950	0.054*
C9	1.01929 (17)	−0.22661 (8)	0.34232 (7)	0.0465 (4)
H9	1.0586	−0.2733	0.3512	0.056*
C10	0.89239 (16)	−0.21934 (7)	0.30344 (6)	0.0379 (3)
H10	0.8443	−0.2610	0.2860	0.045*
C11	0.83581 (13)	−0.15080 (6)	0.29005 (6)	0.0269 (3)
H11	0.7495	−0.1458	0.2631	0.032*
C12	0.78672 (15)	0.00510 (6)	0.42190 (6)	0.0319 (3)
H12	0.7987	−0.0472	0.4331	0.038*
C13	0.84272 (17)	0.05784 (9)	0.47193 (6)	0.0446 (4)
H13A	0.8899	0.0384	0.5128	0.053*
H13B	0.8863	0.1035	0.4552	0.053*
C14	0.68020 (16)	0.04703 (8)	0.46359 (6)	0.0378 (3)
H14A	0.6226	0.0860	0.4417	0.045*
H14B	0.6263	0.0209	0.4993	0.045*
C15	0.67274 (13)	0.13754 (6)	0.11655 (6)	0.0269 (3)
C16	0.72259 (13)	0.14729 (6)	0.05108 (6)	0.0290 (3)
H16	0.8004	0.1180	0.0338	0.035*
C17	0.65736 (14)	0.20020 (7)	0.01143 (6)	0.0346 (3)
H17	0.6903	0.2064	−0.0332	0.042*
C18	0.54501 (15)	0.24393 (7)	0.03623 (7)	0.0369 (3)
H18	0.5017	0.2803	0.0090	0.044*
C19	0.49628 (15)	0.23398 (7)	0.10137 (7)	0.0364 (3)
H19	0.4194	0.2639	0.1185	0.044*
C20	0.55835 (14)	0.18084 (6)	0.14184 (6)	0.0322 (3)
H20	0.5234	0.1741	0.1861	0.039*
H1	0.7554 (18)	0.0673 (10)	0.3395 (8)	0.048 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0784 (7)	0.0231 (4)	0.0230 (4)	0.0114 (4)	0.0030 (4)	−0.0021 (3)
N1	0.0387 (6)	0.0230 (5)	0.0204 (5)	0.0014 (4)	−0.0011 (4)	−0.0008 (3)
N2	0.0302 (5)	0.0259 (5)	0.0226 (5)	−0.0004 (4)	−0.0001 (4)	−0.0016 (4)
N3	0.0610 (7)	0.0201 (5)	0.0197 (5)	−0.0004 (4)	−0.0005 (4)	0.0003 (4)
C1	0.0472 (7)	0.0215 (5)	0.0210 (5)	−0.0018 (5)	−0.0007 (5)	−0.0012 (4)
C2	0.0376 (6)	0.0207 (5)	0.0216 (6)	−0.0036 (4)	−0.0013 (4)	−0.0009 (4)
C3	0.0266 (6)	0.0253 (5)	0.0225 (5)	−0.0039 (4)	−0.0013 (4)	−0.0006 (4)
C4	0.0315 (6)	0.0358 (6)	0.0267 (6)	0.0052 (5)	0.0025 (5)	0.0019 (5)
C5	0.0341 (6)	0.0221 (5)	0.0217 (5)	−0.0075 (4)	−0.0014 (4)	−0.0011 (4)
C6	0.0268 (6)	0.0264 (5)	0.0204 (5)	−0.0019 (4)	0.0012 (4)	0.0017 (4)
C7	0.0273 (6)	0.0524 (8)	0.0235 (5)	−0.0080 (5)	−0.0008 (5)	0.0058 (5)
C8	0.0305 (7)	0.0732 (10)	0.0325 (7)	0.0154 (6)	0.0044 (5)	0.0204 (7)
C9	0.0528 (9)	0.0464 (8)	0.0403 (7)	0.0257 (7)	0.0173 (6)	0.0171 (6)
C10	0.0528 (8)	0.0255 (6)	0.0353 (6)	0.0064 (5)	0.0129 (6)	0.0016 (5)
C11	0.0297 (6)	0.0241 (5)	0.0269 (6)	−0.0004 (4)	0.0018 (4)	−0.0016 (4)
C12	0.0509 (8)	0.0256 (6)	0.0191 (5)	−0.0011 (5)	0.0004 (5)	0.0013 (4)
C13	0.0500 (8)	0.0613 (9)	0.0223 (6)	−0.0220 (7)	0.0007 (5)	−0.0058 (6)
C14	0.0435 (8)	0.0431 (7)	0.0268 (6)	0.0033 (6)	0.0029 (5)	0.0014 (5)
C15	0.0332 (6)	0.0225 (5)	0.0249 (5)	−0.0050 (4)	−0.0058 (4)	−0.0005 (4)
C16	0.0289 (6)	0.0309 (6)	0.0273 (6)	−0.0038 (4)	−0.0025 (4)	0.0033 (5)
C17	0.0336 (7)	0.0391 (7)	0.0310 (6)	−0.0064 (5)	−0.0050 (5)	0.0102 (5)
C18	0.0370 (7)	0.0328 (6)	0.0410 (7)	−0.0004 (5)	−0.0110 (5)	0.0084 (5)
C19	0.0372 (7)	0.0323 (6)	0.0397 (7)	0.0035 (5)	−0.0076 (5)	−0.0035 (5)
C20	0.0394 (7)	0.0293 (6)	0.0280 (6)	−0.0006 (5)	−0.0035 (5)	−0.0033 (5)

O1—C1	1.2525 (15)	C9—H9	0.95
N1—C1	1.3852 (15)	C10—C11	1.3921 (17)
N1—N2	1.4029 (13)	C10—H10	0.95
N1—C15	1.4158 (14)	C11—H11	0.95
N2—C3	1.3130 (15)	C12—C13	1.4869 (17)
N3—C5	1.3260 (15)	C12—C14	1.4885 (18)
N3—C12	1.4382 (15)	C12—H12	1.00
N3—H1	0.917 (18)	C13—C14	1.482 (2)
C1—C2	1.4417 (16)	C13—H13A	0.99
C2—C5	1.4066 (15)	C13—H13B	0.99
C2—C3	1.4345 (15)	C14—H14A	0.99
C3—C4	1.4935 (16)	C14—H14B	0.99
C4—H4A	0.98	C15—C20	1.3978 (17)
C4—H4B	0.98	C15—C16	1.3984 (17)
C4—H4C	0.98	C16—C17	1.3904 (17)
C5—C6	1.4868 (16)	C16—H16	0.95
C6—C11	1.3940 (16)	C17—C18	1.3854 (19)
C6—C7	1.4001 (16)	C17—H17	0.95
C7—C8	1.388 (2)	C18—C19	1.3898 (19)
C7—H7	0.95	C18—H18	0.95
C8—C9	1.383 (2)	C19—C20	1.3912 (17)
C8—H8	0.95	C19—H19	0.95
C9—C10	1.387 (2)	C20—H20	0.95
C1—N1—N2	111.86 (9)	C10—C11—C6	120.38 (12)
C1—N1—C15	128.83 (10)	C10—C11—H11	119.8
N2—N1—C15	119.26 (9)	C6—C11—H11	119.8
C3—N2—N1	106.35 (9)	N3—C12—C13	118.30 (11)
C5—N3—C12	127.99 (10)	N3—C12—C14	116.99 (11)
C5—N3—H1	113.9 (10)	C13—C12—C14	59.76 (9)
C12—N3—H1	117.6 (10)	N3—C12—H12	116.6
O1—C1—N1	126.06 (11)	C13—C12—H12	116.6
O1—C1—C2	129.34 (11)	C14—C12—H12	116.6
N1—C1—C2	104.59 (10)	C14—C13—C12	60.17 (9)
C5—C2—C3	133.14 (11)	C14—C13—H13A	117.8
C5—C2—C1	121.37 (10)	C12—C13—H13A	117.8
C3—C2—C1	105.47 (9)	C14—C13—H13B	117.8
N2—C3—C2	111.64 (10)	C12—C13—H13B	117.8
N2—C3—C4	118.76 (10)	H13A—C13—H13B	114.9
C2—C3—C4	129.60 (10)	C13—C14—C12	60.07 (9)
C3—C4—H4A	109.5	C13—C14—H14A	117.8
C3—C4—H4B	109.5	C12—C14—H14A	117.8
H4A—C4—H4B	109.5	C13—C14—H14B	117.8
C3—C4—H4C	109.5	C12—C14—H14B	117.8
H4A—C4—H4C	109.5	H14A—C14—H14B	114.9
H4B—C4—H4C	109.5	C20—C15—C16	120.12 (11)
N3—C5—C2	117.73 (11)	C20—C15—N1	120.92 (10)
N3—C5—C6	119.45 (10)	C16—C15—N1	118.95 (11)
C2—C5—C6	122.76 (10)	C17—C16—C15	119.52 (12)
C11—C6—C7	119.31 (11)	C17—C16—H16	120.2
C11—C6—C5	119.47 (10)	C15—C16—H16	120.2
C7—C6—C5	121.21 (10)	C18—C17—C16	120.84 (12)
C8—C7—C6	119.90 (12)	C18—C17—H17	119.6
C8—C7—H7	120.0	C16—C17—H17	119.6
C6—C7—H7	120.0	C17—C18—C19	119.29 (11)
C9—C8—C7	120.41 (13)	C17—C18—H18	120.4
C9—C8—H8	119.8	C19—C18—H18	120.4
C7—C8—H8	119.8	C18—C19—C20	121.04 (12)
C8—C9—C10	120.22 (12)	C18—C19—H19	119.5
C8—C9—H9	119.9	C20—C19—H19	119.5
C10—C9—H9	119.9	C19—C20—C15	119.19 (12)
C9—C10—C11	119.77 (13)	C19—C20—H20	120.4
C9—C10—H10	120.1	C15—C20—H20	120.4
C11—C10—H10	120.1
C1—N1—N2—C3	2.41 (13)	C2—C5—C6—C7	122.97 (13)
C15—N1—N2—C3	179.94 (10)	C11—C6—C7—C8	0.19 (17)
N2—N1—C1—O1	176.20 (12)	C5—C6—C7—C8	179.28 (11)
C15—N1—C1—O1	−1.0 (2)	C6—C7—C8—C9	−0.20 (19)
N2—N1—C1—C2	−3.16 (13)	C7—C8—C9—C10	−0.2 (2)
C15—N1—C1—C2	179.61 (11)	C8—C9—C10—C11	0.60 (19)
O1—C1—C2—C5	1.6 (2)	C9—C10—C11—C6	−0.61 (18)
N1—C1—C2—C5	−179.04 (10)	C7—C6—C11—C10	0.21 (17)
O1—C1—C2—C3	−176.70 (13)	C5—C6—C11—C10	−178.89 (11)
N1—C1—C2—C3	2.63 (13)	C5—N3—C12—C13	135.28 (14)
N1—N2—C3—C2	−0.57 (13)	C5—N3—C12—C14	−156.29 (13)
N1—N2—C3—C4	179.70 (10)	N3—C12—C13—C14	106.42 (13)
C5—C2—C3—N2	−179.36 (12)	N3—C12—C14—C13	−108.60 (13)
C1—C2—C3—N2	−1.32 (13)	C1—N1—C15—C20	−19.43 (18)
C5—C2—C3—C4	0.3 (2)	N2—N1—C15—C20	163.52 (10)
C1—C2—C3—C4	178.36 (11)	C1—N1—C15—C16	161.44 (12)
C12—N3—C5—C2	170.89 (12)	N2—N1—C15—C16	−15.61 (15)
C12—N3—C5—C6	−6.43 (19)	C20—C15—C16—C17	−0.12 (17)
C3—C2—C5—N3	170.75 (13)	N1—C15—C16—C17	179.02 (10)
C1—C2—C5—N3	−7.04 (17)	C15—C16—C17—C18	0.82 (18)
C3—C2—C5—C6	−12.0 (2)	C16—C17—C18—C19	−0.70 (19)
C1—C2—C5—C6	170.18 (11)	C17—C18—C19—C20	−0.11 (19)
N3—C5—C6—C11	119.23 (13)	C18—C19—C20—C15	0.80 (19)
C2—C5—C6—C11	−57.95 (16)	C16—C15—C20—C19	−0.68 (17)
N3—C5—C6—C7	−59.85 (16)	N1—C15—C20—C19	−179.80 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1	0.92 (2)	1.88 (2)	2.6726 (15)	143 (2)
C20—H20···O1	0.95	2.36	2.9453 (16)	120
C10—H10···O1i	0.95	2.30	3.1809 (17)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1	0.92 (2)	1.88 (2)	2.6726 (15)	143 (2)
C20—H20⋯O1	0.95	2.36	2.9453 (16)	120
C10—H10⋯O1i	0.95	2.30	3.1809 (17)	154

Symmetry code: (i) .