1,5-Dimethyl-4-[(5-methyl-2-furyl)-methyl-ene-amino]-2-phenyl-1H-pyrazol-3(2H)-one.

In the title compound, C(17)H(17)N(3)O(2), a derivative of 4-amino-anti-pyrine, the structure displays a trans configuration with respect to the imine C=N double bond. The pyrazoline ring is essentially planar and makes a dihedral angle of 55.80 (1)° with the phenyl ring.

Related literature

For related literature, see: Ali et al. (2002 ▶); Allen et al. (1987 ▶); Carlton et al. (1995 ▶); Coolen et al. (1999 ▶); Cukurovali et al. (2002 ▶); Greisen & Andreasen (1976 ▶); Jiang et al. (2000 ▶); Liang et al. (2002 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

C17H17N3O2

M = 295.34

Monoclinic,

a = 11.811 (7) Å

b = 9.997 (6) Å

c = 14.116 (9) Å

β = 110.963 (9)°

V = 1556.4 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.967, T max = 0.967

5012 measured reflections

2670 independent reflections

1904 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.154

S = 1.07

2670 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S1600536808015419/bq2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015419/bq2080Isup2.hkl

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

C17H17N3O2	F000 = 624
Mr = 295.34	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3656 reflections
a = 11.811 (7) Å	θ = 2.6–27.1º
b = 9.997 (6) Å	µ = 0.09 mm−1
c = 14.116 (9) Å	T = 296 K
β = 110.963 (9)º	Block, yellow
V = 1556.4 (16) Å3	0.40 × 0.40 × 0.40 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2670 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.097
T = 296 K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −4→14
Tmin = 0.967, Tmax = 0.967	k = −11→9
5012 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.066	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.5447P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.154	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.17 e Å−3
2670 reflections	Δρmin = −0.17 e Å−3
203 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (4)
Secondary atom site location: difference Fourier map

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	0.46426 (15)	−0.0177 (2)	0.11946 (13)	0.0512 (6)
O2	0.10583 (17)	0.3027 (2)	0.15207 (15)	0.0696 (7)
N1	0.23169 (19)	0.0950 (2)	0.05296 (15)	0.0455 (6)
N2	−0.07371 (19)	0.1894 (2)	−0.08553 (15)	0.0486 (6)
N3	−0.05032 (19)	0.2766 (3)	−0.00250 (16)	0.0519 (7)
C7	0.1172 (2)	0.1547 (3)	0.01786 (18)	0.0433 (7)
C1	0.5813 (2)	−0.0571 (3)	0.1754 (2)	0.0488 (7)
C8	0.0317 (2)	0.1251 (3)	−0.07436 (18)	0.0449 (7)
C10	0.0408 (3)	0.0357 (3)	−0.15564 (19)	0.0576 (8)
H4A	0.0415	0.0887	−0.2121	0.086*
H4B	−0.0275	−0.0238	−0.1773	0.086*
H4C	0.1143	−0.0154	−0.1299	0.086*
C6	0.3099 (2)	0.1276 (3)	0.1398 (2)	0.0547 (8)
H5	0.2884	0.1906	0.1788	0.066*
C9	0.0665 (2)	0.2508 (3)	0.0669 (2)	0.0486 (7)
C2	0.6170 (3)	0.0008 (4)	0.2668 (2)	0.0621 (9)
H7	0.6913	−0.0110	0.3191	0.075*
C12	−0.1484 (3)	0.3267 (3)	0.02341 (19)	0.0511 (8)
C4	0.4294 (2)	0.0702 (3)	0.1788 (2)	0.0525 (8)
C13	−0.2464 (3)	0.2472 (4)	0.0175 (2)	0.0605 (9)
H10	−0.2509	0.1595	−0.0054	0.073*
C3	0.5208 (3)	0.0835 (4)	0.2690 (2)	0.0704 (10)
H11	0.5206	0.1371	0.3227	0.084*
C15	−0.3310 (4)	0.4306 (5)	0.0795 (3)	0.0885 (14)
H12	−0.3929	0.4662	0.0978	0.106*
C17	−0.1411 (3)	0.4580 (4)	0.0576 (2)	0.0673 (9)
H13	−0.0750	0.5113	0.0615	0.081*
C5	0.6407 (3)	−0.1481 (4)	0.1252 (2)	0.0652 (9)
H14A	0.7193	−0.1726	0.1722	0.098*
H14B	0.6492	−0.1038	0.0678	0.098*
H14C	0.5921	−0.2270	0.1029	0.098*
C11	−0.1602 (3)	0.2351 (4)	−0.1828 (2)	0.0852 (13)
H15A	−0.1321	0.3176	−0.2015	0.128*
H15B	−0.2378	0.2492	−0.1769	0.128*
H15C	−0.1675	0.1688	−0.2338	0.128*
C14	−0.3378 (3)	0.2996 (5)	0.0461 (2)	0.0763 (11)
H16	−0.4039	0.2468	0.0429	0.092*
C16	−0.2332 (4)	0.5077 (4)	0.0854 (3)	0.0879 (13)
H17	−0.2288	0.5953	0.1086	0.105*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (11)	0.0633 (14)	0.0496 (10)	0.0038 (10)	0.0134 (8)	−0.0004 (10)
O2	0.0511 (13)	0.0848 (17)	0.0624 (13)	0.0078 (12)	0.0077 (10)	−0.0311 (12)
N1	0.0359 (13)	0.0542 (16)	0.0473 (12)	−0.0030 (11)	0.0159 (10)	−0.0022 (11)
N2	0.0441 (14)	0.0550 (16)	0.0423 (12)	0.0061 (12)	0.0099 (10)	−0.0064 (11)
N3	0.0401 (13)	0.0561 (16)	0.0545 (13)	0.0049 (12)	0.0106 (10)	−0.0120 (12)
C7	0.0361 (15)	0.0492 (18)	0.0442 (14)	−0.0031 (13)	0.0139 (11)	−0.0025 (13)
C1	0.0309 (15)	0.057 (2)	0.0583 (16)	0.0012 (13)	0.0153 (12)	0.0114 (14)
C8	0.0445 (16)	0.0485 (18)	0.0441 (14)	−0.0002 (14)	0.0186 (12)	0.0029 (13)
C10	0.0570 (19)	0.067 (2)	0.0473 (15)	0.0056 (17)	0.0167 (13)	−0.0030 (15)
C6	0.0446 (17)	0.065 (2)	0.0531 (16)	0.0048 (15)	0.0158 (13)	−0.0141 (15)
C9	0.0405 (16)	0.0509 (18)	0.0517 (15)	0.0003 (14)	0.0130 (12)	−0.0094 (14)
C2	0.0388 (16)	0.073 (2)	0.0631 (18)	−0.0015 (17)	0.0039 (13)	−0.0026 (17)
C12	0.0445 (17)	0.054 (2)	0.0485 (15)	0.0101 (15)	0.0083 (12)	0.0002 (14)
C4	0.0373 (16)	0.062 (2)	0.0562 (16)	−0.0004 (14)	0.0146 (13)	−0.0091 (15)
C13	0.0462 (18)	0.067 (2)	0.0596 (17)	0.0060 (17)	0.0080 (14)	−0.0076 (16)
C3	0.0514 (19)	0.086 (3)	0.0624 (18)	0.0040 (19)	0.0064 (15)	−0.0222 (18)
C15	0.060 (2)	0.128 (4)	0.076 (2)	0.039 (3)	0.0220 (18)	−0.011 (2)
C17	0.068 (2)	0.055 (2)	0.076 (2)	0.0100 (18)	0.0231 (17)	−0.0030 (17)
C5	0.0510 (18)	0.081 (3)	0.0661 (18)	0.0154 (18)	0.0237 (15)	0.0138 (18)
C11	0.084 (2)	0.101 (3)	0.0503 (17)	0.032 (2)	−0.0009 (17)	−0.0012 (19)
C14	0.0406 (19)	0.113 (4)	0.069 (2)	0.010 (2)	0.0120 (15)	−0.005 (2)
C16	0.097 (3)	0.075 (3)	0.090 (3)	0.035 (3)	0.030 (2)	−0.009 (2)

O1—C4	1.375 (3)	C2—H7	0.9300
O1—C1	1.382 (3)	C12—C13	1.382 (4)
O2—C9	1.237 (3)	C12—C17	1.390 (4)
N1—C6	1.285 (3)	C4—C3	1.349 (4)
N1—C7	1.397 (3)	C13—C14	1.383 (5)
N2—C8	1.359 (3)	C13—H10	0.9300
N2—N3	1.407 (3)	C3—H11	0.9300
N2—C11	1.461 (3)	C15—C16	1.366 (6)
N3—C9	1.401 (3)	C15—C14	1.384 (6)
N3—C12	1.424 (4)	C15—H12	0.9300
C7—C8	1.364 (3)	C17—C16	1.375 (5)
C7—C9	1.435 (4)	C17—H13	0.9300
C1—C2	1.337 (4)	C5—H14A	0.9600
C1—C5	1.475 (4)	C5—H14B	0.9600
C8—C10	1.488 (4)	C5—H14C	0.9600
C10—H4A	0.9600	C11—H15A	0.9600
C10—H4B	0.9600	C11—H15B	0.9600
C10—H4C	0.9600	C11—H15C	0.9600
C6—C4	1.438 (4)	C14—H16	0.9300
C6—H5	0.9300	C16—H17	0.9300
C2—C3	1.414 (4)
C4—O1—C1	106.9 (2)	C17—C12—N3	117.8 (3)
C6—N1—C7	120.3 (2)	C3—C4—O1	109.0 (3)
C8—N2—N3	107.33 (19)	C3—C4—C6	131.8 (3)
C8—N2—C11	124.1 (2)	O1—C4—C6	119.2 (2)
N3—N2—C11	116.8 (2)	C12—C13—C14	119.3 (3)
C9—N3—N2	108.6 (2)	C12—C13—H10	120.4
C9—N3—C12	124.9 (2)	C14—C13—H10	120.4
N2—N3—C12	119.8 (2)	C4—C3—C2	107.5 (3)
C8—C7—N1	122.5 (2)	C4—C3—H11	126.3
C8—C7—C9	108.2 (2)	C2—C3—H11	126.3
N1—C7—C9	129.3 (2)	C16—C15—C14	120.0 (4)
C2—C1—O1	109.5 (3)	C16—C15—H12	120.0
C2—C1—C5	133.7 (3)	C14—C15—H12	120.0
O1—C1—C5	116.8 (2)	C16—C17—C12	118.9 (4)
N2—C8—C7	110.0 (2)	C16—C17—H13	120.5
N2—C8—C10	120.7 (2)	C12—C17—H13	120.5
C7—C8—C10	129.3 (3)	C1—C5—H14A	109.5
C8—C10—H4A	109.5	C1—C5—H14B	109.5
C8—C10—H4B	109.5	H14A—C5—H14B	109.5
H4A—C10—H4B	109.5	C1—C5—H14C	109.5
C8—C10—H4C	109.5	H14A—C5—H14C	109.5
H4A—C10—H4C	109.5	H14B—C5—H14C	109.5
H4B—C10—H4C	109.5	N2—C11—H15A	109.5
N1—C6—C4	122.4 (3)	N2—C11—H15B	109.5
N1—C6—H5	118.8	H15A—C11—H15B	109.5
C4—C6—H5	118.8	N2—C11—H15C	109.5
O2—C9—N3	122.4 (3)	H15A—C11—H15C	109.5
O2—C9—C7	132.3 (2)	H15B—C11—H15C	109.5
N3—C9—C7	105.2 (2)	C13—C14—C15	120.1 (4)
C1—C2—C3	107.2 (3)	C13—C14—H16	120.0
C1—C2—H7	126.4	C15—C14—H16	120.0
C3—C2—H7	126.4	C15—C16—C17	121.1 (4)
C13—C12—C17	120.7 (3)	C15—C16—H17	119.5
C13—C12—N3	121.6 (3)	C17—C16—H17	119.5