4-[(Ethoxy-imino)(phen-yl)meth-yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one.

In the mol-ecule of the title compound, C(19)H(19)N(3)O(2), the central pyrazole ring makes dihedral angles of 9.89 (3) and 66.06 (5)° with the two phenyl rings, and the two phenyl rings form an angle of 74.05 (5)°. An intra-molecular C-H⋯O hydrogen bond forms a six-membered ring, producing an S(6) ring motif. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link each mol-ecule to two others, forming an infinite one-dimensional supra-molecular structure along the c axis.

Related literature

For related literature, see: Beeam et al. (1984 ▶); Bonati (1980 ▶); Dong & Feng (2006 ▶); Dong et al. (2008a ▶,b ▶); Duan et al. (2007 ▶).

Experimental

Crystal data

C19H19N3O2

M = 321.37

Monoclinic,

a = 13.0046 (15) Å

b = 11.4657 (11) Å

c = 11.6874 (12) Å

β = 99.4530 (10)°

V = 1719.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.50 × 0.18 × 0.16 mm

Data collection

Brucker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.987

8480 measured reflections

3028 independent reflections

1756 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.140

S = 1.02

3028 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536808026263/zl2137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026263/zl2137Isup2.hkl

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

C19H19N3O2	F000 = 680
Mr = 321.37	Dx = 1.242 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1770 reflections
a = 13.0046 (15) Å	θ = 2.4–22.5º
b = 11.4657 (11) Å	µ = 0.08 mm−1
c = 11.6874 (12) Å	T = 298 (2) K
β = 99.4530 (10)º	Prismatic, colorless
V = 1719.0 (3) Å3	0.50 × 0.18 × 0.16 mm
Z = 4

Brucker SMART 1000 CCD area-detector diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.960, Tmax = 0.987	k = −13→9
8480 measured reflections	l = −13→13

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.0591P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3028 reflections	Δρmax = 0.17 e Å−3
219 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.53222 (14)	0.34824 (17)	−0.06367 (17)	0.0486 (5)
N2	0.84502 (13)	0.23475 (16)	0.16076 (15)	0.0369 (5)
N3	0.78882 (13)	0.29323 (15)	0.23325 (15)	0.0386 (5)
H3	0.8064	0.2996	0.3072	0.046*
O1	0.49758 (11)	0.28139 (15)	0.02320 (14)	0.0546 (5)
O2	0.82634 (12)	0.20296 (15)	−0.03673 (13)	0.0529 (5)
C1	0.38665 (18)	0.2834 (2)	0.0039 (3)	0.0623 (8)
H1A	0.3595	0.2505	−0.0715	0.075*
H1B	0.3617	0.3630	0.0061	0.075*
C2	0.3515 (2)	0.2130 (3)	0.0975 (3)	0.0805 (10)
H2A	0.3776	0.1349	0.0954	0.121*
H2B	0.2767	0.2113	0.0859	0.121*
H2C	0.3774	0.2474	0.1715	0.121*
C3	0.63196 (17)	0.35862 (19)	−0.04638 (19)	0.0395 (6)
C4	0.70377 (15)	0.31546 (19)	0.05486 (18)	0.0363 (5)
C5	0.79385 (17)	0.24753 (19)	0.04860 (19)	0.0371 (5)
C6	0.70309 (16)	0.33834 (19)	0.17079 (19)	0.0360 (5)
C7	0.62708 (17)	0.4013 (2)	0.2301 (2)	0.0496 (7)
H7A	0.5735	0.3484	0.2446	0.074*
H7B	0.5964	0.4640	0.1817	0.074*
H7C	0.6622	0.4323	0.3023	0.074*
C8	0.67571 (18)	0.4228 (2)	−0.1379 (2)	0.0432 (6)
C9	0.6212 (2)	0.4282 (2)	−0.2505 (2)	0.0576 (7)
H9	0.5572	0.3908	−0.2688	0.069*
C10	0.6611 (3)	0.4881 (3)	−0.3347 (3)	0.0755 (9)
H10	0.6238	0.4914	−0.4097	0.091*
C11	0.7555 (3)	0.5432 (3)	−0.3093 (3)	0.0773 (9)
H11	0.7823	0.5832	−0.3671	0.093*
C12	0.8107 (2)	0.5397 (2)	−0.1988 (3)	0.0664 (8)
H12	0.8743	0.5782	−0.1811	0.080*
C13	0.77084 (19)	0.4782 (2)	−0.1138 (2)	0.0516 (7)
H13	0.8089	0.4743	−0.0393	0.062*
C14	0.94564 (15)	0.19033 (19)	0.20265 (19)	0.0358 (5)
C15	0.99788 (18)	0.2239 (2)	0.3093 (2)	0.0517 (7)
H15	0.9678	0.2775	0.3535	0.062*
C16	1.09499 (19)	0.1782 (3)	0.3508 (2)	0.0659 (8)
H16	1.1296	0.2005	0.4235	0.079*
C17	1.1406 (2)	0.1007 (3)	0.2862 (3)	0.0667 (8)
H17	1.2063	0.0706	0.3143	0.080*
C18	1.0891 (2)	0.0678 (2)	0.1801 (3)	0.0647 (8)
H18	1.1203	0.0153	0.1358	0.078*
C19	0.99121 (17)	0.1113 (2)	0.1374 (2)	0.0520 (7)
H19	0.9564	0.0875	0.0652	0.062*

	U11	U22	U33	U12	U13	U23
N1	0.0485 (12)	0.0550 (13)	0.0405 (13)	0.0035 (10)	0.0019 (10)	0.0055 (10)
N2	0.0349 (10)	0.0546 (12)	0.0209 (10)	0.0067 (8)	0.0036 (8)	0.0001 (9)
N3	0.0394 (10)	0.0560 (12)	0.0200 (10)	0.0020 (9)	0.0038 (8)	−0.0052 (9)
O1	0.0391 (9)	0.0719 (12)	0.0507 (11)	−0.0002 (8)	0.0010 (8)	0.0123 (9)
O2	0.0585 (10)	0.0778 (12)	0.0223 (9)	0.0200 (9)	0.0069 (8)	−0.0005 (8)
C1	0.0402 (14)	0.0705 (19)	0.073 (2)	0.0002 (13)	−0.0002 (14)	0.0023 (16)
C2	0.0532 (17)	0.109 (3)	0.080 (2)	−0.0073 (16)	0.0143 (16)	0.007 (2)
C3	0.0398 (13)	0.0446 (14)	0.0328 (13)	0.0031 (10)	0.0020 (10)	−0.0023 (11)
C4	0.0359 (12)	0.0465 (13)	0.0258 (13)	−0.0004 (10)	0.0034 (10)	0.0039 (10)
C5	0.0396 (12)	0.0490 (14)	0.0225 (12)	0.0010 (10)	0.0039 (10)	0.0016 (11)
C6	0.0354 (12)	0.0423 (13)	0.0297 (13)	−0.0027 (10)	0.0036 (10)	0.0004 (10)
C7	0.0479 (14)	0.0618 (16)	0.0400 (15)	0.0050 (12)	0.0098 (12)	−0.0069 (13)
C8	0.0518 (14)	0.0436 (14)	0.0332 (14)	0.0124 (12)	0.0038 (11)	0.0021 (11)
C9	0.0661 (17)	0.0619 (17)	0.0428 (17)	0.0110 (14)	0.0026 (14)	0.0081 (14)
C10	0.096 (2)	0.084 (2)	0.0456 (19)	0.0188 (19)	0.0093 (17)	0.0216 (17)
C11	0.101 (3)	0.076 (2)	0.062 (2)	0.0172 (19)	0.034 (2)	0.0259 (17)
C12	0.0723 (19)	0.0598 (18)	0.072 (2)	0.0014 (15)	0.0254 (17)	0.0119 (16)
C13	0.0570 (16)	0.0532 (16)	0.0447 (16)	0.0036 (13)	0.0088 (13)	0.0033 (13)
C14	0.0325 (12)	0.0446 (13)	0.0293 (13)	0.0011 (10)	0.0025 (10)	0.0048 (11)
C15	0.0437 (14)	0.0661 (17)	0.0423 (16)	0.0060 (12)	−0.0023 (12)	−0.0078 (13)
C16	0.0507 (16)	0.086 (2)	0.0528 (18)	0.0087 (15)	−0.0162 (14)	−0.0103 (16)
C17	0.0473 (15)	0.080 (2)	0.066 (2)	0.0174 (15)	−0.0093 (15)	0.0000 (17)
C18	0.0568 (16)	0.0708 (19)	0.065 (2)	0.0203 (14)	0.0056 (15)	−0.0057 (16)
C19	0.0487 (14)	0.0649 (17)	0.0395 (15)	0.0124 (13)	−0.0011 (12)	−0.0048 (13)

N1—C3	1.285 (3)	C8—C13	1.378 (3)
N1—O1	1.404 (2)	C8—C9	1.389 (3)
N2—C5	1.377 (3)	C9—C10	1.371 (4)
N2—N3	1.380 (2)	C9—H9	0.9300
N2—C14	1.415 (3)	C10—C11	1.369 (4)
N3—C6	1.333 (3)	C10—H10	0.9300
N3—H3	0.8600	C11—C12	1.371 (4)
O1—C1	1.423 (3)	C11—H11	0.9300
O2—C5	1.254 (2)	C12—C13	1.386 (3)
C1—C2	1.491 (4)	C12—H12	0.9300
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.373 (3)
C2—H2A	0.9600	C14—C19	1.379 (3)
C2—H2B	0.9600	C15—C16	1.380 (3)
C2—H2C	0.9600	C15—H15	0.9300
C3—C4	1.468 (3)	C16—C17	1.363 (3)
C3—C8	1.487 (3)	C16—H16	0.9300
C4—C6	1.382 (3)	C17—C18	1.362 (4)
C4—C5	1.419 (3)	C17—H17	0.9300
C6—C7	1.485 (3)	C18—C19	1.383 (3)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—H19	0.9300
C7—H7C	0.9600
C3—N1—O1	111.86 (18)	H7B—C7—H7C	109.5
C5—N2—N3	108.11 (16)	C13—C8—C9	118.3 (2)
C5—N2—C14	130.00 (18)	C13—C8—C3	121.2 (2)
N3—N2—C14	121.03 (17)	C9—C8—C3	120.5 (2)
C6—N3—N2	109.39 (17)	C10—C9—C8	120.5 (3)
C6—N3—H3	125.3	C10—C9—H9	119.7
N2—N3—H3	125.3	C8—C9—H9	119.7
N1—O1—C1	108.28 (17)	C11—C10—C9	120.5 (3)
O1—C1—C2	107.5 (2)	C11—C10—H10	119.7
O1—C1—H1A	110.2	C9—C10—H10	119.7
C2—C1—H1A	110.2	C10—C11—C12	120.2 (3)
O1—C1—H1B	110.2	C10—C11—H11	119.9
C2—C1—H1B	110.2	C12—C11—H11	119.9
H1A—C1—H1B	108.5	C11—C12—C13	119.4 (3)
C1—C2—H2A	109.5	C11—C12—H12	120.3
C1—C2—H2B	109.5	C13—C12—H12	120.3
H2A—C2—H2B	109.5	C8—C13—C12	121.1 (3)
C1—C2—H2C	109.5	C8—C13—H13	119.5
H2A—C2—H2C	109.5	C12—C13—H13	119.5
H2B—C2—H2C	109.5	C15—C14—C19	119.5 (2)
N1—C3—C4	126.0 (2)	C15—C14—N2	120.3 (2)
N1—C3—C8	115.4 (2)	C19—C14—N2	120.1 (2)
C4—C3—C8	118.62 (19)	C14—C15—C16	120.0 (2)
C6—C4—C5	107.05 (19)	C14—C15—H15	120.0
C6—C4—C3	128.4 (2)	C16—C15—H15	120.0
C5—C4—C3	124.40 (19)	C17—C16—C15	120.6 (3)
O2—C5—N2	122.71 (19)	C17—C16—H16	119.7
O2—C5—C4	130.8 (2)	C15—C16—H16	119.7
N2—C5—C4	106.46 (18)	C18—C17—C16	119.4 (2)
N3—C6—C4	108.91 (19)	C18—C17—H17	120.3
N3—C6—C7	119.62 (19)	C16—C17—H17	120.3
C4—C6—C7	131.5 (2)	C17—C18—C19	121.0 (3)
C6—C7—H7A	109.5	C17—C18—H18	119.5
C6—C7—H7B	109.5	C19—C18—H18	119.5
H7A—C7—H7B	109.5	C14—C19—C18	119.4 (2)
C6—C7—H7C	109.5	C14—C19—H19	120.3
H7A—C7—H7C	109.5	C18—C19—H19	120.3
C5—N2—N3—C6	2.1 (2)	N1—C3—C8—C13	155.2 (2)
C14—N2—N3—C6	172.45 (18)	C4—C3—C8—C13	−23.6 (3)
C3—N1—O1—C1	174.5 (2)	N1—C3—C8—C9	−24.8 (3)
N1—O1—C1—C2	−179.5 (2)	C4—C3—C8—C9	156.4 (2)
O1—N1—C3—C4	−4.5 (3)	C13—C8—C9—C10	−0.6 (4)
O1—N1—C3—C8	176.79 (17)	C3—C8—C9—C10	179.4 (2)
N1—C3—C4—C6	−55.2 (4)	C8—C9—C10—C11	0.3 (4)
C8—C3—C4—C6	123.5 (2)	C9—C10—C11—C12	−0.5 (4)
N1—C3—C4—C5	130.1 (2)	C10—C11—C12—C13	1.1 (4)
C8—C3—C4—C5	−51.3 (3)	C9—C8—C13—C12	1.1 (3)
N3—N2—C5—O2	−179.5 (2)	C3—C8—C13—C12	−178.9 (2)
C14—N2—C5—O2	11.3 (4)	C11—C12—C13—C8	−1.4 (4)
N3—N2—C5—C4	−0.3 (2)	C5—N2—C14—C15	155.0 (2)
C14—N2—C5—C4	−169.5 (2)	N3—N2—C14—C15	−13.0 (3)
C6—C4—C5—O2	177.7 (2)	C5—N2—C14—C19	−26.1 (3)
C3—C4—C5—O2	−6.7 (4)	N3—N2—C14—C19	165.9 (2)
C6—C4—C5—N2	−1.4 (2)	C19—C14—C15—C16	−0.4 (4)
C3—C4—C5—N2	174.25 (19)	N2—C14—C15—C16	178.5 (2)
N2—N3—C6—C4	−3.0 (2)	C14—C15—C16—C17	0.9 (4)
N2—N3—C6—C7	177.33 (17)	C15—C16—C17—C18	−0.5 (4)
C5—C4—C6—N3	2.8 (2)	C16—C17—C18—C19	−0.3 (4)
C3—C4—C6—N3	−172.7 (2)	C15—C14—C19—C18	−0.4 (4)
C5—C4—C6—C7	−177.7 (2)	N2—C14—C19—C18	−179.3 (2)
C3—C4—C6—C7	6.9 (4)	C17—C18—C19—C14	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2i	0.86	1.80	2.653 (2)	171
C15—H15···O2i	0.93	2.42	3.200 (3)	141
C19—H19···O2	0.93	2.32	2.900 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2i	0.86	1.80	2.653 (2)	171
C15—H15⋯O2i	0.93	2.42	3.200 (3)	141
C19—H19⋯O2	0.93	2.32	2.900 (3)	120

Symmetry code: (i) .