(Z)-4-[(Ethyl-amino)(furan-2-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the crystal of the title compound, C(17)H(17)N(3)O(2), the mol-ecules exist in the keto-enamine form. The pyrazole ring is oriented at 10.59 (4) and 57.98 (5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains along the b axis.

Related literature

For general background to acyl­pyrazolo­nes, see: Dong et al. (1983 ▶); Casas et al. (2007 ▶). For related structures, see: Zhang et al. (2007 ▶); Li et al. (2009 ▶); Wang (2010 ▶).

Experimental

Crystal data

C17H17N3O2

M = 295.34

Orthorhombic,

a = 8.5729 (13) Å

b = 17.555 (3) Å

c = 20.427 (3) Å

V = 3074.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer

14892 measured reflections

3552 independent reflections

2271 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.153

S = 1.02

3552 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013712/xu5499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013712/xu5499Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013712/xu5499Isup3.cml

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

C17H17N3O2	F(000) = 1248
Mr = 295.34	Dx = 1.276 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3420 reflections
a = 8.5729 (13) Å	θ = 2.5–24.5°
b = 17.555 (3) Å	µ = 0.09 mm−1
c = 20.427 (3) Å	T = 296 K
V = 3074.2 (8) Å3	Block, yellow
Z = 8	0.20 × 0.18 × 0.16 mm

Bruker SMART 1000 CCD diffractometer	2271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.6°, θmin = 2.5°
ω scans	h = −11→11
14892 measured reflections	k = −22→14
3552 independent reflections	l = −26→25

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.073P)2 + 0.6048P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3552 reflections	Δρmax = 0.29 e Å−3
202 parameters	Δρmin = −0.24 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: 0.0061 (11)

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
C1	0.3274 (2)	0.36448 (10)	0.37402 (8)	0.0470 (4)
C2	0.4490 (2)	0.31933 (11)	0.35231 (9)	0.0568 (5)
H2	0.4819	0.3221	0.3090	0.068*
C3	0.5211 (2)	0.27020 (12)	0.39536 (10)	0.0673 (6)
H3	0.6030	0.2399	0.3807	0.081*
C4	0.4740 (3)	0.26520 (13)	0.45952 (11)	0.0719 (6)
H4	0.5234	0.2317	0.4881	0.086*
C5	0.3540 (2)	0.30984 (13)	0.48091 (10)	0.0676 (6)
H5	0.3219	0.3067	0.5243	0.081*
C6	0.2797 (2)	0.35970 (12)	0.43881 (9)	0.0561 (5)
H6	0.1981	0.3899	0.4538	0.067*
C7	0.2554 (2)	0.42127 (10)	0.26479 (8)	0.0500 (4)
C8	0.1713 (2)	0.48955 (10)	0.24974 (8)	0.0479 (4)
C9	0.1213 (2)	0.51919 (11)	0.31153 (9)	0.0502 (4)
C10	0.0283 (3)	0.58819 (12)	0.32686 (10)	0.0672 (6)
H10A	−0.0075	0.5856	0.3713	0.101*
H10B	−0.0597	0.5909	0.2979	0.101*
H10C	0.0921	0.6327	0.3213	0.101*
C11	0.1465 (2)	0.51345 (10)	0.18519 (9)	0.0506 (4)
C12	0.0770 (2)	0.58668 (10)	0.16927 (9)	0.0526 (5)
C13	−0.0461 (2)	0.60530 (12)	0.13197 (9)	0.0561 (5)
H13	−0.1068	0.5722	0.1072	0.067*
C14	−0.0655 (3)	0.68398 (15)	0.13746 (12)	0.0791 (7)
H14	−0.1426	0.7132	0.1175	0.095*
C15	0.0474 (3)	0.70936 (13)	0.17668 (12)	0.0834 (7)
H15	0.0622	0.7600	0.1884	0.100*
C16	0.1841 (3)	0.48181 (15)	0.06678 (10)	0.0774 (7)
H16A	0.2017	0.5355	0.0585	0.093*
H16B	0.0818	0.4686	0.0500	0.093*
C17	0.3046 (3)	0.43617 (17)	0.03265 (11)	0.0931 (8)
H17A	0.4054	0.4478	0.0506	0.140*
H17B	0.3036	0.4482	−0.0132	0.140*
H17C	0.2829	0.3829	0.0385	0.140*
N1	0.25453 (19)	0.41740 (8)	0.33228 (6)	0.0506 (4)
N2	0.16849 (17)	0.47679 (9)	0.36000 (7)	0.0530 (4)
N3	0.1892 (2)	0.46750 (9)	0.13692 (7)	0.0637 (5)
H3A	0.2364	0.4192	0.1514	0.076*
O1	0.31504 (18)	0.37337 (8)	0.22731 (6)	0.0658 (4)
O2	0.13911 (19)	0.64946 (9)	0.19731 (8)	0.0768 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0528 (9)	0.0412 (9)	0.0472 (9)	−0.0088 (8)	−0.0069 (7)	0.0016 (7)
C2	0.0628 (11)	0.0525 (11)	0.0552 (10)	−0.0007 (9)	−0.0040 (9)	−0.0025 (8)
C3	0.0633 (12)	0.0594 (13)	0.0793 (14)	0.0061 (10)	−0.0146 (11)	−0.0005 (11)
C4	0.0719 (13)	0.0688 (14)	0.0752 (14)	−0.0025 (12)	−0.0224 (11)	0.0189 (11)
C5	0.0685 (13)	0.0798 (15)	0.0546 (11)	−0.0114 (12)	−0.0103 (9)	0.0163 (11)
C6	0.0566 (10)	0.0607 (12)	0.0511 (10)	−0.0051 (9)	−0.0034 (8)	0.0052 (9)
C7	0.0609 (10)	0.0444 (10)	0.0446 (9)	−0.0025 (9)	−0.0018 (8)	−0.0005 (7)
C8	0.0544 (10)	0.0414 (9)	0.0477 (9)	−0.0033 (8)	−0.0040 (7)	0.0015 (8)
C9	0.0505 (9)	0.0460 (10)	0.0543 (10)	−0.0028 (8)	−0.0012 (8)	0.0005 (8)
C10	0.0674 (12)	0.0613 (13)	0.0728 (13)	0.0131 (11)	0.0052 (10)	−0.0014 (10)
C11	0.0555 (10)	0.0440 (10)	0.0523 (10)	−0.0102 (8)	−0.0052 (8)	0.0043 (8)
C12	0.0509 (10)	0.0480 (11)	0.0589 (11)	−0.0072 (8)	−0.0006 (8)	0.0074 (8)
C13	0.0508 (10)	0.0590 (12)	0.0583 (10)	−0.0014 (9)	−0.0078 (8)	0.0080 (9)
C14	0.0757 (14)	0.0754 (16)	0.0862 (16)	0.0254 (13)	0.0148 (13)	0.0283 (13)
C15	0.108 (2)	0.0462 (13)	0.0959 (17)	−0.0016 (13)	0.0296 (16)	0.0002 (12)
C16	0.1008 (17)	0.0840 (17)	0.0474 (11)	0.0017 (14)	−0.0064 (11)	0.0079 (11)
C17	0.119 (2)	0.101 (2)	0.0587 (13)	0.0073 (17)	0.0081 (13)	−0.0057 (13)
N1	0.0654 (9)	0.0447 (9)	0.0416 (7)	0.0042 (7)	−0.0013 (7)	0.0002 (6)
N2	0.0606 (9)	0.0494 (9)	0.0490 (8)	0.0035 (7)	0.0022 (7)	−0.0035 (7)
N3	0.0953 (13)	0.0510 (10)	0.0447 (8)	0.0010 (9)	−0.0074 (8)	0.0033 (7)
O1	0.0989 (11)	0.0512 (8)	0.0471 (7)	0.0146 (7)	−0.0001 (7)	−0.0042 (6)
O2	0.0834 (10)	0.0573 (9)	0.0896 (11)	−0.0112 (8)	−0.0091 (8)	0.0004 (8)

C1—C2	1.382 (3)	C10—H10C	0.9600
C1—C6	1.388 (3)	C11—N3	1.325 (2)
C1—N1	1.407 (2)	C11—C12	1.454 (3)
C2—C3	1.378 (3)	C12—C13	1.342 (2)
C2—H2	0.9300	C12—O2	1.352 (2)
C3—C4	1.374 (3)	C13—C14	1.396 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.365 (3)	C14—C15	1.333 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.382 (3)	C15—O2	1.379 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—N3	1.455 (2)
C7—O1	1.247 (2)	C16—C17	1.482 (3)
C7—N1	1.380 (2)	C16—H16A	0.9700
C7—C8	1.432 (3)	C16—H16B	0.9700
C8—C11	1.400 (2)	C17—H17A	0.9600
C8—C9	1.431 (2)	C17—H17B	0.9600
C9—N2	1.303 (2)	C17—H17C	0.9600
C9—C10	1.483 (3)	N1—N2	1.397 (2)
C10—H10A	0.9600	N3—H3A	0.9845
C10—H10B	0.9600
C2—C1—C6	119.58 (17)	N3—C11—C12	119.01 (16)
C2—C1—N1	121.26 (16)	C8—C11—C12	122.55 (17)
C6—C1—N1	119.12 (16)	C13—C12—O2	110.60 (17)
C3—C2—C1	119.48 (18)	C13—C12—C11	131.66 (18)
C3—C2—H2	120.3	O2—C12—C11	117.69 (16)
C1—C2—H2	120.3	C12—C13—C14	106.80 (19)
C4—C3—C2	121.1 (2)	C12—C13—H13	126.6
C4—C3—H3	119.4	C14—C13—H13	126.6
C2—C3—H3	119.4	C15—C14—C13	107.0 (2)
C5—C4—C3	119.3 (2)	C15—C14—H14	126.5
C5—C4—H4	120.3	C13—C14—H14	126.5
C3—C4—H4	120.3	C14—C15—O2	110.0 (2)
C4—C5—C6	120.8 (2)	C14—C15—H15	125.0
C4—C5—H5	119.6	O2—C15—H15	125.0
C6—C5—H5	119.6	N3—C16—C17	110.42 (19)
C5—C6—C1	119.7 (2)	N3—C16—H16A	109.6
C5—C6—H6	120.2	C17—C16—H16A	109.6
C1—C6—H6	120.2	N3—C16—H16B	109.6
O1—C7—N1	125.63 (17)	C17—C16—H16B	109.6
O1—C7—C8	129.72 (16)	H16A—C16—H16B	108.1
N1—C7—C8	104.63 (15)	C16—C17—H17A	109.5
C11—C8—C9	132.56 (17)	C16—C17—H17B	109.5
C11—C8—C7	121.97 (16)	H17A—C17—H17B	109.5
C9—C8—C7	105.42 (15)	C16—C17—H17C	109.5
N2—C9—C8	111.69 (16)	H17A—C17—H17C	109.5
N2—C9—C10	118.21 (16)	H17B—C17—H17C	109.5
C8—C9—C10	130.09 (17)	C7—N1—N2	111.78 (14)
C9—C10—H10A	109.5	C7—N1—C1	129.42 (15)
C9—C10—H10B	109.5	N2—N1—C1	118.80 (13)
H10A—C10—H10B	109.5	C9—N2—N1	106.40 (14)
C9—C10—H10C	109.5	C11—N3—C16	128.24 (18)
H10A—C10—H10C	109.5	C11—N3—H3A	114.4
H10B—C10—H10C	109.5	C16—N3—H3A	117.2
N3—C11—C8	118.44 (17)	C12—O2—C15	105.52 (17)
C6—C1—C2—C3	0.0 (3)	C8—C11—C12—O2	51.5 (2)
N1—C1—C2—C3	177.63 (17)	O2—C12—C13—C14	−1.2 (2)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C14	176.4 (2)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—C15	1.0 (2)
C3—C4—C5—C6	0.1 (3)	C13—C14—C15—O2	−0.5 (3)
C4—C5—C6—C1	0.0 (3)	O1—C7—N1—N2	−175.51 (18)
C2—C1—C6—C5	−0.1 (3)	C8—C7—N1—N2	3.0 (2)
N1—C1—C6—C5	−177.75 (17)	O1—C7—N1—C1	5.4 (3)
O1—C7—C8—C11	−1.4 (3)	C8—C7—N1—C1	−176.05 (17)
N1—C7—C8—C11	−179.86 (16)	C2—C1—N1—C7	18.6 (3)
O1—C7—C8—C9	176.14 (19)	C6—C1—N1—C7	−163.80 (18)
N1—C7—C8—C9	−2.32 (19)	C2—C1—N1—N2	−160.46 (16)
C11—C8—C9—N2	178.07 (19)	C6—C1—N1—N2	17.2 (2)
C7—C8—C9—N2	0.9 (2)	C8—C9—N2—N1	0.9 (2)
C11—C8—C9—C10	−2.1 (3)	C10—C9—N2—N1	−178.91 (15)
C7—C8—C9—C10	−179.30 (19)	C7—N1—N2—C9	−2.5 (2)
C9—C8—C11—N3	−170.12 (19)	C1—N1—N2—C9	176.65 (15)
C7—C8—C11—N3	6.7 (3)	C8—C11—N3—C16	−175.9 (2)
C9—C8—C11—C12	10.3 (3)	C12—C11—N3—C16	3.7 (3)
C7—C8—C11—C12	−172.87 (17)	C17—C16—N3—C11	153.0 (2)
N3—C11—C12—C13	54.5 (3)	C13—C12—O2—C15	0.9 (2)
C8—C11—C12—C13	−125.9 (2)	C11—C12—O2—C15	−177.06 (17)
N3—C11—C12—O2	−128.04 (19)	C14—C15—O2—C12	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.98	1.87	2.702 (2)	140
C15—H15···O1i	0.93	2.39	3.279 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.98	1.87	2.702 (2)	140
C15—H15⋯O1i	0.93	2.39	3.279 (3)	161

Symmetry code: (i) .