4-[(1-Hy-droxy-2-naphth-yl)methyl-ene-amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

The title anti-pyrine derivative, C(22)H(19)N(3)O(2), was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one and 1-hy-droxy-naphthalene-2-carbaldehyde in methanol solution. As expected, the compound adopts a trans configuration about the central C=N bond. The N atom is involved in an intra-molecular O-H⋯N bond which stabilizes the mol-ecular configuration. In the crystal structure, adjacent mol-ecules stack with no short contacts.

Related literature

For background to the applications of anti­pyrine derivatives, see: Bashkatova et al. (2005 ▶); Bansal et al. (2007 ▶); Bondock et al. (2008 ▶); Capel et al. (1978 ▶); Coolen et al. (1999 ▶); Collado et al. (2000 ▶); Cunha et al. (2005 ▶); Evstropov et al. (1992 ▶); Khanduja et al. (1984 ▶); Madiha et al. (2007 ▶); Plesch et al. (1987 ▶); Radzikowska et al. (1995 ▶); Rehim et al. (2001 ▶); Turan-Zitouni et al. (2001 ▶); Yadav et al. (2003 ▶). For some typical structures of anti­pyrine derivatives, see: Liang et al. (2002 ▶); Li & Zhang (2004 ▶, 2005 ▶); Sun, Xie et al. (2006 ▶); Sun, Zhang, Jin et al. (2006 ▶); Sun, Zhang, Wang et al. (2006 ▶); Sun, Hao, Wei et al. (2009 ▶); Wen et al. (2005 ▶); You et al. (2004 ▶, 2006 ▶); Zhang & Li et al. (2005 ▶). For related structures involving Schiff bases, see: Ali et al. (2002 ▶); Bashkatova et al. (2005 ▶); Coolen et al. (1999 ▶); Collado et al. (2000 ▶); Cukurovali et al. (2002 ▶); Farag et al. (2009 ▶); Rehim et al. (2001 ▶); Sun, Hao, Yu et al. (2009 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

C22H19N3O2

M = 357.40

Monoclinic,

a = 8.0636 (7) Å

b = 7.4407 (6) Å

c = 30.169 (3) Å

β = 94.329 (2)°

V = 1804.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.23 × 0.10 × 0.02 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.998

14746 measured reflections

3942 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.147

S = 1.04

3942 reflections

252 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT-Plus (Bruker, 2002 ▶); data reduction: SAINT-Plus; 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/S1600536810026450/gw2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026450/gw2081Isup2.hkl

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

C22H19N3O2	F(000) = 752
Mr = 357.40	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1592 reflections
a = 8.0636 (7) Å	θ = 2.5–25.1°
b = 7.4407 (6) Å	µ = 0.09 mm−1
c = 30.169 (3) Å	T = 295 K
β = 94.329 (2)°	Plane, yellow
V = 1804.9 (3) Å3	0.23 × 0.10 × 0.02 mm
Z = 4

Bruker APEX area-detector diffractometer	3942 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.981, Tmax = 0.998	k = −9→9
14746 measured reflections	l = −37→38

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.2473P] where P = (Fo2 + 2Fc2)/3
3942 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.17 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	Occ. (<1)
O1	0.5537 (2)	0.63818 (19)	0.63468 (5)	0.0518 (4)
O2	0.2652 (2)	0.2809 (2)	0.48208 (5)	0.0529 (5)
H2	0.3246	0.2763	0.5053	0.079*
N1	0.6496 (2)	0.3617 (2)	0.66126 (6)	0.0430 (5)
N2	0.6208 (2)	0.1816 (2)	0.64902 (6)	0.0440 (5)
N3	0.4118 (2)	0.3947 (2)	0.55528 (6)	0.0391 (4)
C1	0.6836 (3)	0.4067 (3)	0.70681 (7)	0.0416 (5)
C2	0.7888 (3)	0.5480 (3)	0.71763 (8)	0.0546 (6)
H2A	0.8380	0.6109	0.6954	0.066*
C3	0.8210 (3)	0.5961 (4)	0.76159 (9)	0.0662 (8)
H3	0.8910	0.6926	0.7690	0.079*
C4	0.7503 (4)	0.5023 (4)	0.79433 (9)	0.0699 (8)
H4	0.7726	0.5351	0.8239	0.084*
C5	0.6471 (4)	0.3607 (4)	0.78370 (8)	0.0633 (7)
H5	0.6007	0.2963	0.8061	0.076*
C6	0.6115 (3)	0.3130 (3)	0.73982 (8)	0.0526 (6)
H6	0.5393	0.2182	0.7325	0.063*
C7	0.5673 (3)	0.4746 (3)	0.62969 (7)	0.0383 (5)
C8	0.5054 (3)	0.3554 (3)	0.59459 (7)	0.0366 (5)
C9	0.5442 (3)	0.1841 (3)	0.60707 (7)	0.0408 (5)
C10	0.513 (2)	0.016 (3)	0.5821 (7)	0.0599 (11)	0.68 (4)
H10A	0.4444	0.0406	0.5554	0.090*	0.68 (4)
H10B	0.4572	−0.0679	0.6001	0.090*	0.68 (4)
H10C	0.6168	−0.0343	0.5746	0.090*	0.68 (4)
C10'	0.501 (5)	0.018 (7)	0.5804 (16)	0.0599 (11)	0.32 (4)
H10D	0.3824	0.0105	0.5746	0.090*	0.32 (4)
H10E	0.5402	−0.0861	0.5969	0.090*	0.32 (4)
H10F	0.5525	0.0231	0.5528	0.090*	0.32 (4)
C11	0.7486 (3)	0.0508 (3)	0.66333 (8)	0.0575 (7)
H11A	0.7126	−0.0673	0.6541	0.086*
H11B	0.7672	0.0539	0.6951	0.086*
H11C	0.8501	0.0797	0.6502	0.086*
C12	0.3597 (3)	0.5544 (3)	0.54508 (7)	0.0412 (5)
H12	0.3903	0.6499	0.5638	0.049*
C13	0.2085 (3)	0.4488 (3)	0.47564 (7)	0.0404 (5)
C14	0.2546 (3)	0.5875 (3)	0.50496 (7)	0.0382 (5)
C15	0.1916 (3)	0.7620 (3)	0.49565 (8)	0.0496 (6)
H15	0.2230	0.8555	0.5150	0.059*
C16	0.0877 (3)	0.7968 (3)	0.45970 (8)	0.0562 (7)
H16	0.0489	0.9132	0.4546	0.067*
C17	0.0366 (3)	0.6577 (3)	0.42957 (7)	0.0497 (6)
C18	0.0988 (3)	0.4819 (3)	0.43735 (7)	0.0444 (6)
C19	0.0465 (3)	0.3427 (4)	0.40779 (8)	0.0570 (7)
H19	0.0867	0.2266	0.4126	0.068*
C20	−0.0626 (4)	0.3776 (5)	0.37217 (9)	0.0740 (9)
H20	−0.0968	0.2849	0.3529	0.089*
C21	−0.1237 (3)	0.5509 (5)	0.36419 (9)	0.0755 (9)
H21	−0.1976	0.5730	0.3396	0.091*
C22	−0.0758 (3)	0.6875 (4)	0.39216 (8)	0.0660 (8)
H22	−0.1178	0.8024	0.3866	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0777 (12)	0.0296 (9)	0.0462 (10)	0.0008 (8)	−0.0081 (8)	−0.0028 (7)
O2	0.0680 (12)	0.0423 (10)	0.0465 (10)	0.0065 (8)	−0.0091 (8)	−0.0060 (8)
N1	0.0618 (12)	0.0285 (10)	0.0368 (10)	−0.0024 (9)	−0.0082 (9)	−0.0010 (8)
N2	0.0610 (13)	0.0258 (10)	0.0432 (11)	0.0017 (9)	−0.0086 (9)	0.0001 (8)
N3	0.0464 (11)	0.0342 (10)	0.0362 (10)	0.0010 (8)	0.0006 (8)	−0.0002 (8)
C1	0.0508 (14)	0.0365 (12)	0.0359 (12)	0.0005 (10)	−0.0071 (10)	0.0004 (10)
C2	0.0617 (16)	0.0486 (15)	0.0519 (15)	−0.0066 (12)	−0.0064 (13)	−0.0003 (12)
C3	0.0732 (19)	0.0597 (18)	0.0620 (18)	−0.0080 (15)	−0.0195 (15)	−0.0113 (15)
C4	0.095 (2)	0.071 (2)	0.0398 (15)	0.0118 (17)	−0.0171 (15)	−0.0065 (14)
C5	0.088 (2)	0.0609 (17)	0.0401 (15)	0.0049 (16)	0.0006 (14)	0.0079 (13)
C6	0.0630 (16)	0.0472 (15)	0.0461 (15)	−0.0066 (12)	−0.0055 (12)	0.0051 (11)
C7	0.0456 (13)	0.0316 (12)	0.0372 (12)	−0.0003 (10)	−0.0001 (10)	0.0023 (9)
C8	0.0416 (12)	0.0305 (11)	0.0372 (12)	−0.0015 (10)	−0.0014 (10)	−0.0018 (9)
C9	0.0476 (13)	0.0349 (12)	0.0395 (13)	−0.0029 (10)	0.0003 (10)	−0.0028 (9)
C10	0.091 (3)	0.0295 (14)	0.057 (2)	0.000 (2)	−0.013 (3)	−0.0056 (15)
C10'	0.091 (3)	0.0295 (14)	0.057 (2)	0.000 (2)	−0.013 (3)	−0.0056 (15)
C11	0.0692 (17)	0.0410 (14)	0.0601 (16)	0.0112 (12)	−0.0110 (13)	0.0041 (12)
C12	0.0460 (13)	0.0374 (13)	0.0401 (13)	−0.0028 (10)	0.0019 (10)	−0.0029 (10)
C13	0.0434 (13)	0.0402 (13)	0.0379 (12)	−0.0006 (10)	0.0048 (10)	0.0023 (10)
C14	0.0410 (12)	0.0358 (12)	0.0377 (12)	−0.0015 (10)	0.0031 (10)	0.0029 (9)
C15	0.0563 (15)	0.0399 (13)	0.0519 (15)	0.0023 (11)	−0.0003 (12)	0.0023 (11)
C16	0.0575 (16)	0.0499 (15)	0.0604 (17)	0.0077 (13)	0.0001 (13)	0.0140 (13)
C17	0.0417 (14)	0.0658 (17)	0.0417 (14)	0.0009 (12)	0.0027 (11)	0.0149 (12)
C18	0.0413 (13)	0.0564 (15)	0.0357 (12)	−0.0070 (11)	0.0043 (10)	0.0045 (11)
C19	0.0570 (16)	0.0698 (18)	0.0435 (14)	−0.0126 (13)	−0.0011 (12)	−0.0044 (13)
C20	0.0669 (19)	0.105 (3)	0.0485 (17)	−0.0213 (18)	−0.0042 (14)	−0.0058 (17)
C21	0.0522 (17)	0.131 (3)	0.0420 (16)	−0.0102 (19)	−0.0091 (13)	0.0173 (18)
C22	0.0512 (16)	0.093 (2)	0.0533 (17)	0.0027 (15)	−0.0003 (13)	0.0269 (16)

O1—C7	1.232 (2)	C10—H10C	0.9600
O2—C13	1.340 (2)	C10'—H10D	0.9600
O2—H2	0.8200	C10'—H10E	0.9600
N1—C7	1.399 (3)	C10'—H10F	0.9600
N1—N2	1.405 (2)	C11—H11A	0.9600
N1—C1	1.421 (3)	C11—H11B	0.9600
N2—C9	1.366 (3)	C11—H11C	0.9600
N2—C11	1.459 (3)	C12—C14	1.445 (3)
N3—C12	1.290 (3)	C12—H12	0.9300
N3—C8	1.388 (3)	C13—C14	1.391 (3)
C1—C2	1.375 (3)	C13—C18	1.422 (3)
C1—C6	1.380 (3)	C14—C15	1.415 (3)
C2—C3	1.379 (3)	C15—C16	1.345 (3)
C2—H2A	0.9300	C15—H15	0.9300
C3—C4	1.369 (4)	C16—C17	1.418 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.365 (4)	C17—C22	1.411 (3)
C4—H4	0.9300	C17—C18	1.414 (3)
C5—C6	1.380 (3)	C18—C19	1.410 (3)
C5—H5	0.9300	C19—C20	1.362 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.441 (3)	C20—C21	1.395 (4)
C8—C9	1.359 (3)	C20—H20	0.9300
C9—C10	1.47 (3)	C21—C22	1.358 (4)
C9—C10'	1.50 (6)	C21—H21	0.9300
C10—H10A	0.9600	C22—H22	0.9300
C10—H10B	0.9600
C13—O2—H2	109.5	H10D—C10'—H10E	109.5
C7—N1—N2	109.49 (16)	C9—C10'—H10F	109.5
C7—N1—C1	124.31 (17)	H10D—C10'—H10F	109.5
N2—N1—C1	119.69 (16)	H10E—C10'—H10F	109.5
C9—N2—N1	106.54 (16)	N2—C11—H11A	109.5
C9—N2—C11	122.92 (18)	N2—C11—H11B	109.5
N1—N2—C11	117.36 (18)	H11A—C11—H11B	109.5
C12—N3—C8	123.00 (18)	N2—C11—H11C	109.5
C2—C1—C6	120.1 (2)	H11A—C11—H11C	109.5
C2—C1—N1	118.7 (2)	H11B—C11—H11C	109.5
C6—C1—N1	121.2 (2)	N3—C12—C14	121.1 (2)
C1—C2—C3	119.7 (2)	N3—C12—H12	119.4
C1—C2—H2A	120.2	C14—C12—H12	119.4
C3—C2—H2A	120.2	O2—C13—C14	121.88 (19)
C4—C3—C2	120.2 (3)	O2—C13—C18	117.6 (2)
C4—C3—H3	119.9	C14—C13—C18	120.5 (2)
C2—C3—H3	119.9	C13—C14—C15	118.7 (2)
C5—C4—C3	120.2 (2)	C13—C14—C12	121.15 (19)
C5—C4—H4	119.9	C15—C14—C12	120.1 (2)
C3—C4—H4	119.9	C16—C15—C14	122.0 (2)
C4—C5—C6	120.2 (3)	C16—C15—H15	119.0
C4—C5—H5	119.9	C14—C15—H15	119.0
C6—C5—H5	119.9	C15—C16—C17	120.7 (2)
C5—C6—C1	119.6 (2)	C15—C16—H16	119.7
C5—C6—H6	120.2	C17—C16—H16	119.7
C1—C6—H6	120.2	C22—C17—C18	118.5 (2)
O1—C7—N1	123.52 (19)	C22—C17—C16	122.4 (2)
O1—C7—C8	131.94 (19)	C18—C17—C16	119.1 (2)
N1—C7—C8	104.51 (17)	C19—C18—C17	119.3 (2)
C9—C8—N3	122.23 (19)	C19—C18—C13	121.6 (2)
C9—C8—C7	108.31 (19)	C17—C18—C13	119.1 (2)
N3—C8—C7	129.33 (18)	C20—C19—C18	120.2 (3)
C8—C9—N2	110.37 (18)	C20—C19—H19	119.9
C8—C9—C10	128.9 (9)	C18—C19—H19	119.9
N2—C9—C10	120.7 (9)	C19—C20—C21	120.8 (3)
C8—C9—C10'	125.8 (18)	C19—C20—H20	119.6
N2—C9—C10'	123.7 (18)	C21—C20—H20	119.6
C10—C9—C10'	4(2)	C22—C21—C20	120.3 (3)
C9—C10—H10A	109.5	C22—C21—H21	119.9
C9—C10—H10B	109.5	C20—C21—H21	119.9
C9—C10—H10C	109.5	C21—C22—C17	121.0 (3)
C9—C10'—H10D	109.5	C21—C22—H22	119.5
C9—C10'—H10E	109.5	C17—C22—H22	119.5
C7—N1—N2—C9	9.2 (2)	C11—N2—C9—C8	−147.1 (2)
C1—N1—N2—C9	162.14 (19)	N1—N2—C9—C10	173.1 (9)
C7—N1—N2—C11	151.62 (19)	C11—N2—C9—C10	33.4 (9)
C1—N1—N2—C11	−55.5 (3)	N1—N2—C9—C10'	176.1 (18)
C7—N1—C1—C2	−64.1 (3)	C11—N2—C9—C10'	36.4 (18)
N2—N1—C1—C2	147.2 (2)	C8—N3—C12—C14	−176.44 (19)
C7—N1—C1—C6	115.0 (2)	O2—C13—C14—C15	179.1 (2)
N2—N1—C1—C6	−33.6 (3)	C18—C13—C14—C15	−0.7 (3)
C6—C1—C2—C3	−0.4 (4)	O2—C13—C14—C12	−3.1 (3)
N1—C1—C2—C3	178.8 (2)	C18—C13—C14—C12	177.09 (19)
C1—C2—C3—C4	0.8 (4)	N3—C12—C14—C13	−1.2 (3)
C2—C3—C4—C5	−0.1 (4)	N3—C12—C14—C15	176.6 (2)
C3—C4—C5—C6	−1.0 (4)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C1	1.4 (4)	C12—C14—C15—C16	−177.1 (2)
C2—C1—C6—C5	−0.7 (4)	C14—C15—C16—C17	0.2 (4)
N1—C1—C6—C5	−179.9 (2)	C15—C16—C17—C22	178.2 (2)
N2—N1—C7—O1	170.7 (2)	C15—C16—C17—C18	−1.1 (3)
C1—N1—C7—O1	19.4 (3)	C22—C17—C18—C19	−0.2 (3)
N2—N1—C7—C8	−7.4 (2)	C16—C17—C18—C19	179.1 (2)
C1—N1—C7—C8	−158.8 (2)	C22—C17—C18—C13	−178.2 (2)
C12—N3—C8—C9	172.8 (2)	C16—C17—C18—C13	1.1 (3)
C12—N3—C8—C7	−2.5 (3)	O2—C13—C18—C19	2.0 (3)
O1—C7—C8—C9	−175.0 (2)	C14—C13—C18—C19	−178.2 (2)
N1—C7—C8—C9	2.9 (2)	O2—C13—C18—C17	179.96 (19)
O1—C7—C8—N3	0.8 (4)	C14—C13—C18—C17	−0.2 (3)
N1—C7—C8—N3	178.7 (2)	C17—C18—C19—C20	0.0 (3)
N3—C8—C9—N2	−173.34 (19)	C13—C18—C19—C20	178.0 (2)
C7—C8—C9—N2	2.8 (3)	C18—C19—C20—C21	0.3 (4)
N3—C8—C9—C10	6.1 (10)	C19—C20—C21—C22	−0.5 (4)
C7—C8—C9—C10	−177.7 (9)	C20—C21—C22—C17	0.3 (4)
N3—C8—C9—C10'	3.1 (18)	C18—C17—C22—C21	0.1 (4)
C7—C8—C9—C10'	179.3 (18)	C16—C17—C22—C21	−179.2 (2)
N1—N2—C9—C8	−7.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3	0.82	1.84	2.569 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3	0.82	1.84	2.569 (2)	148