4-[(E)-(4-Diethyl­amino-2-hy­droxy­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Manvizhi, K.; Chakkaravarthi, G.; Anbalagan, G.; Rajagopal, G.

doi:10.1107/S1600536811037615

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2692

https://doi.org/10.1107/S1600536811037615

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4-[(E)-(4-Diethylamino-2-hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

K. Manvizhi,^a G. Chakkaravarthi,^b ^* G. Anbalagan ^c and G. Rajagopal ^d ^*

^aDepartment of Chemistry, Anand Institute of Higher Technology, Kazhipattur, Chennai 603 103, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^dDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 15 August 2011; accepted 14 September 2011; online 20 September 2011)

In the title compound, C₂₂H₂₆N₄O₂, the phenyl ring and hydroxybenzene group are twisted with respect to the central pyrazolone ring, making dihedral angles of 54.05 (5) and 21.80 (6)°, respectively. One of the ethyl groups is disordered over two positions with site occupancies of 0.872 (6) and 0.128 (6). The molecular structure features short intramolecular O—H⋯N and C—H⋯O contacts. The crystal packing exhibits weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For biological activities of pyrazolone derivatives, see: Gursoy et al. (2000 ); Ragavan et al. (2009 ). For related structures, see: Wang et al. (2007 ); Zhu et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₆N₄O₂
M_r = 378.47
Monoclinic, C 2/c
a = 17.2794 (6) Å
b = 7.1853 (3) Å
c = 32.9711 (12) Å
β = 101.652 (1)°
V = 4009.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.977, T_max = 0.984
21210 measured reflections
4398 independent reflections
3293 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.126
S = 1.03
4398 reflections
274 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N2/C7/C8/C9 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N3	0.82	1.88	2.6127 (17)	148
C12—H12⋯O1	0.93	2.33	3.004 (2)	130
C2—H2⋯O2ⁱ	0.93	2.48	3.267 (2)	142
C11—H11B⋯O1ⁱⁱ	0.96	2.36	3.309 (2)	172
C4—H4⋯Cg2ⁱⁱⁱ	0.93	2.89	3.746 (2)	153
C6—H6⋯Cg1^iv	0.93	2.78	3.559 (2)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) x, y-1, z; (iii) $[x, -y, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037615/gk2400sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037615/gk2400Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037615/gk2400Isup3.cml

checkCIF report

Comment top

Pyrazolone derivatives exhibit antipyretic, anti-inflammatory, antibacterial and antifungal (Gursoy et al., 2000; Ragavan et al., 2009) activities. The geometric parameters of the title compound, (Fig. 1) agree well with the reported similar structures (Wang et al., 2007; Zhu et al., 2008).

The phenyl ring (C1–C6) and hydroxybenzene group (C13–C18) are twisted with respect to the pyrazolone ring (N1/N2/C7/C8/C9), making the dihedral angles of and 54.05 (5) and 21.80 (6)°, respectively. One of the ethyl groups is disordered over two positions with site occupancies of 0.872 (6) and 0.128 (6). The molecular structure is stabilized by weak intramolecular O—H···N and C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O and C—H···π interactions (Table 1 & Fig. 2).

Related literature top

For biological activities of pyrazolone derivatives, see: Gursoy et al. (2000); Ragavan et al. (2009). For related structures, see: Wang et al. (2007); Zhu et al. (2008).

Experimental top

A solution of 1-phenyl-2,3-dimethyl-4-amino-3-pyrazolin-5-one (0.203 g, 1 mmol) in ethanol (5 ml) was added to a solution of 4-diethylamino-2-hydroxybenzaldehyde (0.193 g, 1 mmol) in ethanol (5 ml). The reaction mixture was stirred for 2 h at room temperature then heated to reflux for 2 h and kept at 273 K for 4h. The characteristic pale-green precipitate obtained was filtered and recrystallized by dissolving in methanol (m.p. 438 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Structure description top

For biological activities of pyrazolone derivatives, see: Gursoy et al. (2000); Ragavan et al. (2009). For related structures, see: Wang et al. (2007); Zhu et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

4-[(E)-(4-Diethylamino-2-hydroxybenzylidene)amino]-1,5-dimethyl- 2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₂H₂₆N₄O₂	F(000) = 1616
M_r = 378.47	D_x = 1.254 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 22393 reflections
a = 17.2794 (6) Å	θ = 2.4–27.1°
b = 7.1853 (3) Å	µ = 0.08 mm⁻¹
c = 32.9711 (12) Å	T = 295 K
β = 101.652 (1)°	Block, colourless
V = 4009.3 (3) Å³	0.28 × 0.24 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	4398 independent reflections
Radiation source: fine-focus sealed tube	3293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→22
T_min = 0.977, T_max = 0.984	k = −8→9
21210 measured reflections	l = −42→41

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.052P)² + 2.4774P] where P = (F_o² + 2F_c²)/3
4398 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.33 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₂H₂₆N₄O₂	V = 4009.3 (3) Å³
M_r = 378.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.2794 (6) Å	µ = 0.08 mm⁻¹
b = 7.1853 (3) Å	T = 295 K
c = 32.9711 (12) Å	0.28 × 0.24 × 0.20 mm
β = 101.652 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	4398 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3293 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.029
21210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
4398 reflections	Δρ_min = −0.18 e Å⁻³
274 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.45300 (7)	0.35172 (17)	0.64038 (4)	0.0550 (3)
O2	0.70119 (7)	−0.04760 (16)	0.59423 (4)	0.0509 (3)
H2A	0.6621	−0.0508	0.6048	0.076*
N1	0.41671 (8)	0.09879 (18)	0.67543 (4)	0.0421 (3)
N2	0.45087 (8)	−0.07360 (18)	0.68900 (4)	0.0427 (3)
N3	0.58759 (8)	0.08183 (19)	0.62786 (4)	0.0415 (3)
N4	0.87010 (11)	0.3824 (2)	0.54493 (6)	0.0730 (5)
C1	0.37186 (9)	0.1964 (2)	0.70049 (5)	0.0392 (4)
C2	0.31096 (10)	0.3083 (2)	0.68109 (5)	0.0473 (4)
H2	0.2973	0.3121	0.6523	0.057*
C3	0.27040 (10)	0.4148 (3)	0.70461 (6)	0.0529 (4)
H3	0.2295	0.4916	0.6916	0.063*
C4	0.28989 (10)	0.4086 (3)	0.74715 (6)	0.0511 (4)
H4	0.2628	0.4818	0.7629	0.061*
C5	0.34974 (10)	0.2935 (3)	0.76613 (5)	0.0505 (4)
H5	0.3625	0.2877	0.7949	0.061*
C6	0.39114 (10)	0.1864 (2)	0.74313 (5)	0.0456 (4)
H6	0.4315	0.1085	0.7562	0.055*
C7	0.51277 (9)	−0.0988 (2)	0.66911 (5)	0.0403 (4)
C8	0.52434 (9)	0.0572 (2)	0.64794 (5)	0.0396 (4)
C9	0.46392 (9)	0.1904 (2)	0.65229 (5)	0.0404 (4)
C10	0.39353 (12)	−0.2229 (3)	0.69031 (7)	0.0615 (5)
H10A	0.3620	−0.2414	0.6631	0.092*
H10B	0.3600	−0.1891	0.7090	0.092*
H10C	0.4211	−0.3359	0.6996	0.092*
C11	0.55860 (11)	−0.2746 (2)	0.67399 (6)	0.0568 (5)
H11A	0.6023	−0.2638	0.6602	0.085*
H11B	0.5251	−0.3753	0.6621	0.085*
H11C	0.5781	−0.2985	0.7029	0.085*
C12	0.60614 (10)	0.2457 (2)	0.61670 (5)	0.0443 (4)
H12	0.5753	0.3467	0.6212	0.053*
C13	0.67255 (10)	0.2769 (2)	0.59774 (5)	0.0423 (4)
C14	0.71893 (10)	0.1312 (2)	0.58723 (5)	0.0413 (4)
C15	0.78306 (11)	0.1657 (2)	0.56953 (6)	0.0518 (4)
H15	0.8120	0.0662	0.5624	0.062*
C16	0.80566 (11)	0.3479 (3)	0.56208 (6)	0.0534 (5)
C17	0.75989 (12)	0.4944 (3)	0.57316 (6)	0.0572 (5)
H17	0.7736	0.6170	0.5690	0.069*
C18	0.69576 (11)	0.4578 (2)	0.58988 (6)	0.0544 (5)
H18	0.6660	0.5572	0.5964	0.065*
C19	0.90916 (13)	0.2322 (3)	0.52606 (7)	0.0717 (6)
H19A	0.9297	0.2818	0.5030	0.086*
H19B	0.8708	0.1365	0.5155	0.086*
C20	0.97484 (16)	0.1490 (4)	0.55681 (9)	0.0939 (8)
H20A	1.0114	0.2448	0.5684	0.141*
H20B	1.0016	0.0576	0.5434	0.141*
H20C	0.9539	0.0908	0.5785	0.141*
C21	0.90416 (14)	0.5704 (4)	0.54439 (8)	0.0585 (8)	0.872 (6)
H21A	0.9610	0.5611	0.5474	0.070*	0.872 (6)
H21B	0.8932	0.6419	0.5675	0.070*	0.872 (6)
C22	0.87019 (19)	0.6673 (5)	0.50495 (9)	0.0881 (11)	0.872 (6)
H22A	0.8930	0.7892	0.5051	0.132*	0.872 (6)
H22B	0.8140	0.6781	0.5022	0.132*	0.872 (6)
H22C	0.8816	0.5972	0.4821	0.132*	0.872 (6)
C21A	0.8615 (8)	0.5403 (16)	0.5143 (3)	0.051 (5)	0.128 (6)
H21C	0.8079	0.5875	0.5079	0.062*	0.128 (6)
H21D	0.8775	0.5039	0.4889	0.062*	0.128 (6)
C22A	0.9190 (13)	0.6828 (18)	0.5389 (6)	0.092 (8)	0.128 (6)
H22D	0.9194	0.7934	0.5226	0.139*	0.128 (6)
H22E	0.9712	0.6306	0.5453	0.139*	0.128 (6)
H22F	0.9022	0.7133	0.5641	0.139*	0.128 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0649 (8)	0.0415 (7)	0.0644 (8)	0.0090 (6)	0.0270 (6)	0.0139 (6)
O2	0.0591 (7)	0.0380 (6)	0.0599 (8)	0.0027 (5)	0.0222 (6)	0.0033 (5)
N1	0.0471 (7)	0.0356 (7)	0.0455 (8)	0.0029 (6)	0.0140 (6)	0.0042 (6)
N2	0.0473 (8)	0.0321 (7)	0.0508 (8)	−0.0009 (6)	0.0152 (6)	0.0029 (6)
N3	0.0456 (7)	0.0420 (8)	0.0383 (7)	−0.0003 (6)	0.0116 (6)	−0.0009 (6)
N4	0.0753 (11)	0.0561 (10)	0.1027 (14)	0.0042 (9)	0.0540 (11)	0.0114 (10)
C1	0.0371 (8)	0.0373 (8)	0.0447 (9)	−0.0034 (6)	0.0117 (7)	0.0018 (7)
C2	0.0460 (9)	0.0501 (10)	0.0442 (9)	0.0038 (8)	0.0057 (7)	0.0050 (8)
C3	0.0444 (9)	0.0506 (10)	0.0637 (12)	0.0102 (8)	0.0111 (8)	0.0072 (9)
C4	0.0493 (10)	0.0489 (10)	0.0599 (11)	0.0029 (8)	0.0220 (8)	−0.0030 (8)
C5	0.0510 (10)	0.0596 (11)	0.0423 (9)	0.0001 (9)	0.0127 (8)	0.0000 (8)
C6	0.0403 (8)	0.0505 (10)	0.0463 (9)	0.0049 (7)	0.0094 (7)	0.0075 (8)
C7	0.0443 (9)	0.0355 (8)	0.0408 (8)	−0.0031 (7)	0.0079 (7)	−0.0049 (7)
C8	0.0443 (8)	0.0380 (8)	0.0367 (8)	−0.0015 (7)	0.0089 (7)	−0.0033 (7)
C9	0.0456 (9)	0.0374 (9)	0.0391 (8)	−0.0009 (7)	0.0107 (7)	0.0025 (7)
C10	0.0621 (11)	0.0438 (10)	0.0835 (14)	−0.0112 (9)	0.0260 (10)	0.0030 (10)
C11	0.0640 (11)	0.0408 (10)	0.0684 (12)	0.0062 (8)	0.0200 (10)	0.0021 (9)
C12	0.0506 (9)	0.0395 (9)	0.0453 (9)	0.0040 (7)	0.0155 (8)	−0.0003 (7)
C13	0.0485 (9)	0.0392 (9)	0.0416 (9)	0.0032 (7)	0.0146 (7)	0.0028 (7)
C14	0.0499 (9)	0.0366 (9)	0.0373 (8)	0.0019 (7)	0.0086 (7)	0.0034 (7)
C15	0.0548 (10)	0.0448 (10)	0.0614 (11)	0.0085 (8)	0.0251 (9)	0.0027 (8)
C16	0.0563 (10)	0.0502 (10)	0.0591 (11)	0.0029 (8)	0.0244 (9)	0.0083 (9)
C17	0.0679 (12)	0.0398 (10)	0.0710 (12)	−0.0001 (9)	0.0310 (10)	0.0076 (9)
C18	0.0639 (11)	0.0381 (9)	0.0681 (12)	0.0055 (8)	0.0298 (10)	0.0035 (8)
C19	0.0736 (14)	0.0761 (15)	0.0746 (14)	0.0043 (12)	0.0364 (12)	0.0106 (12)
C20	0.0863 (17)	0.098 (2)	0.102 (2)	0.0101 (15)	0.0298 (15)	0.0236 (16)
C21	0.0556 (14)	0.0675 (18)	0.0537 (15)	−0.0115 (12)	0.0141 (12)	0.0029 (13)
C22	0.103 (2)	0.093 (3)	0.0670 (18)	−0.0082 (19)	0.0142 (17)	0.0196 (17)
C21A	0.066 (10)	0.051 (10)	0.045 (9)	−0.005 (7)	0.028 (8)	0.015 (7)
C22A	0.109 (17)	0.061 (14)	0.105 (19)	−0.019 (12)	0.016 (14)	−0.003 (13)

Geometric parameters (Å, º) top

O1—C9	1.2260 (19)	C11—H11B	0.9600
O2—C14	1.3514 (19)	C11—H11C	0.9600
O2—H2A	0.8200	C12—C13	1.431 (2)
N1—C9	1.390 (2)	C12—H12	0.9300
N1—N2	1.4058 (18)	C13—C18	1.400 (2)
N1—C1	1.426 (2)	C13—C14	1.404 (2)
N2—C7	1.375 (2)	C14—C15	1.375 (2)
N2—C10	1.467 (2)	C15—C16	1.402 (3)
N3—C12	1.293 (2)	C15—H15	0.9300
N3—C8	1.399 (2)	C16—C17	1.408 (3)
N4—C16	1.369 (2)	C17—C18	1.359 (2)
N4—C21	1.475 (3)	C17—H17	0.9300
N4—C19	1.475 (3)	C18—H18	0.9300
N4—C21A	1.506 (9)	C19—C20	1.486 (3)
C1—C2	1.375 (2)	C19—H19A	0.9700
C1—C6	1.380 (2)	C19—H19B	0.9700
C2—C3	1.378 (2)	C20—H20A	0.9600
C2—H2	0.9300	C20—H20B	0.9600
C3—C4	1.375 (3)	C20—H20C	0.9600
C3—H3	0.9300	C21—C22	1.487 (4)
C4—C5	1.372 (2)	C21—H21A	0.9700
C4—H4	0.9300	C21—H21B	0.9700
C5—C6	1.378 (2)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C8	1.357 (2)	C21A—C22A	1.538 (10)
C7—C11	1.482 (2)	C21A—H21C	0.9700
C8—C9	1.445 (2)	C21A—H21D	0.9700
C10—H10A	0.9600	C22A—H22D	0.9600
C10—H10B	0.9600	C22A—H22E	0.9600
C10—H10C	0.9600	C22A—H22F	0.9600
C11—H11A	0.9600

C14—O2—H2A	109.5	C18—C13—C14	116.60 (15)
C9—N1—N2	109.69 (12)	C18—C13—C12	120.76 (15)
C9—N1—C1	122.18 (13)	C14—C13—C12	122.61 (15)
N2—N1—C1	119.43 (12)	O2—C14—C15	118.29 (15)
C7—N2—N1	106.34 (12)	O2—C14—C13	120.43 (14)
C7—N2—C10	120.86 (14)	C15—C14—C13	121.28 (15)
N1—N2—C10	114.28 (13)	C14—C15—C16	121.32 (16)
C12—N3—C8	120.80 (14)	C14—C15—H15	119.3
C16—N4—C21	122.02 (17)	C16—C15—H15	119.3
C16—N4—C19	121.42 (17)	N4—C16—C15	121.31 (17)
C21—N4—C19	116.56 (16)	N4—C16—C17	121.21 (17)
C16—N4—C21A	115.8 (6)	C15—C16—C17	117.47 (16)
C19—N4—C21A	105.1 (5)	C18—C17—C16	120.49 (17)
C2—C1—C6	120.60 (15)	C18—C17—H17	119.8
C2—C1—N1	118.19 (14)	C16—C17—H17	119.8
C6—C1—N1	121.13 (14)	C17—C18—C13	122.82 (16)
C1—C2—C3	119.43 (16)	C17—C18—H18	118.6
C1—C2—H2	120.3	C13—C18—H18	118.6
C3—C2—H2	120.3	N4—C19—C20	111.0 (2)
C4—C3—C2	120.56 (16)	N4—C19—H19A	109.4
C4—C3—H3	119.7	C20—C19—H19A	109.4
C2—C3—H3	119.7	N4—C19—H19B	109.4
C5—C4—C3	119.43 (16)	C20—C19—H19B	109.4
C5—C4—H4	120.3	H19A—C19—H19B	108.0
C3—C4—H4	120.3	C19—C20—H20A	109.5
C4—C5—C6	120.85 (17)	C19—C20—H20B	109.5
C4—C5—H5	119.6	H20A—C20—H20B	109.5
C6—C5—H5	119.6	C19—C20—H20C	109.5
C5—C6—C1	119.11 (16)	H20A—C20—H20C	109.5
C5—C6—H6	120.4	H20B—C20—H20C	109.5
C1—C6—H6	120.4	N4—C21—C22	110.6 (2)
C8—C7—N2	110.26 (14)	N4—C21—H21A	109.5
C8—C7—C11	128.98 (15)	C22—C21—H21A	109.5
N2—C7—C11	120.70 (14)	N4—C21—H21B	109.5
C7—C8—N3	123.96 (15)	C22—C21—H21B	109.5
C7—C8—C9	108.17 (14)	H21A—C21—H21B	108.1
N3—C8—C9	127.78 (14)	C21—C22—H22A	109.5
O1—C9—N1	123.66 (15)	C21—C22—H22B	109.5
O1—C9—C8	131.45 (15)	H22A—C22—H22B	109.5
N1—C9—C8	104.87 (13)	C21—C22—H22C	109.5
N2—C10—H10A	109.5	H22A—C22—H22C	109.5
N2—C10—H10B	109.5	H22B—C22—H22C	109.5
H10A—C10—H10B	109.5	N4—C21A—C22A	100.5 (8)
N2—C10—H10C	109.5	N4—C21A—H21C	111.7
H10A—C10—H10C	109.5	C22A—C21A—H21C	111.7
H10B—C10—H10C	109.5	N4—C21A—H21D	111.7
C7—C11—H11A	109.5	C22A—C21A—H21D	111.7
C7—C11—H11B	109.5	H21C—C21A—H21D	109.4
H11A—C11—H11B	109.5	C21A—C22A—H22D	109.5
C7—C11—H11C	109.5	C21A—C22A—H22E	109.5
H11A—C11—H11C	109.5	H22D—C22A—H22E	109.5
H11B—C11—H11C	109.5	C21A—C22A—H22F	109.5
N3—C12—C13	122.26 (15)	H22D—C22A—H22F	109.5
N3—C12—H12	118.9	H22E—C22A—H22F	109.5
C13—C12—H12	118.9

C9—N1—N2—C7	−8.57 (17)	N3—C8—C9—N1	−178.70 (15)
C1—N1—N2—C7	−156.94 (13)	C8—N3—C12—C13	177.22 (15)
C9—N1—N2—C10	−144.52 (15)	N3—C12—C13—C18	−173.45 (17)
C1—N1—N2—C10	67.11 (19)	N3—C12—C13—C14	4.6 (3)
C9—N1—C1—C2	65.9 (2)	C18—C13—C14—O2	179.23 (16)
N2—N1—C1—C2	−149.84 (15)	C12—C13—C14—O2	1.1 (2)
C9—N1—C1—C6	−111.09 (18)	C18—C13—C14—C15	−1.0 (2)
N2—N1—C1—C6	33.2 (2)	C12—C13—C14—C15	−179.12 (17)
C6—C1—C2—C3	1.7 (3)	O2—C14—C15—C16	−178.86 (17)
N1—C1—C2—C3	−175.26 (15)	C13—C14—C15—C16	1.4 (3)
C1—C2—C3—C4	−0.6 (3)	C21—N4—C16—C15	−167.7 (2)
C2—C3—C4—C5	−0.7 (3)	C19—N4—C16—C15	12.2 (3)
C3—C4—C5—C6	0.9 (3)	C21A—N4—C16—C15	141.5 (6)
C4—C5—C6—C1	0.2 (3)	C21—N4—C16—C17	11.9 (3)
C2—C1—C6—C5	−1.5 (2)	C19—N4—C16—C17	−168.2 (2)
N1—C1—C6—C5	175.37 (15)	C21A—N4—C16—C17	−39.0 (6)
N1—N2—C7—C8	7.11 (18)	C14—C15—C16—N4	179.18 (18)
C10—N2—C7—C8	139.51 (16)	C14—C15—C16—C17	−0.4 (3)
N1—N2—C7—C11	−175.49 (14)	N4—C16—C17—C18	179.5 (2)
C10—N2—C7—C11	−43.1 (2)	C15—C16—C17—C18	−0.9 (3)
N2—C7—C8—N3	173.56 (14)	C16—C17—C18—C13	1.3 (3)
C11—C7—C8—N3	−3.6 (3)	C14—C13—C18—C17	−0.3 (3)
N2—C7—C8—C9	−3.09 (18)	C12—C13—C18—C17	177.84 (18)
C11—C7—C8—C9	179.78 (16)	C16—N4—C19—C20	−92.3 (3)
C12—N3—C8—C7	−163.62 (16)	C21—N4—C19—C20	87.6 (2)
C12—N3—C8—C9	12.3 (2)	C21A—N4—C19—C20	133.9 (6)
N2—N1—C9—O1	−171.84 (16)	C16—N4—C21—C22	−93.5 (3)
C1—N1—C9—O1	−24.5 (2)	C19—N4—C21—C22	86.6 (3)
N2—N1—C9—C8	6.62 (17)	C21A—N4—C21—C22	2.0 (8)
C1—N1—C9—C8	153.96 (14)	C16—N4—C21A—C22A	110.9 (11)
C7—C8—C9—O1	176.07 (18)	C21—N4—C21A—C22A	0.5 (10)
N3—C8—C9—O1	−0.4 (3)	C19—N4—C21A—C22A	−112.3 (11)
C7—C8—C9—N1	−2.22 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C7/C8/C9 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3	0.82	1.88	2.6127 (17)	148
C12—H12···O1	0.93	2.33	3.004 (2)	130
C2—H2···O2ⁱ	0.93	2.48	3.267 (2)	142
C11—H11B···O1ⁱⁱ	0.96	2.36	3.309 (2)	172
C4—H4···Cg2ⁱⁱⁱ	0.93	2.89	3.746 (2)	153
C6—H6···Cg1^iv	0.93	2.78	3.559 (2)	142

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, y−1, z; (iii) x, −y, z+1/2; (iv) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₄O₂
M_r	378.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	17.2794 (6), 7.1853 (3), 32.9711 (12)
β (°)	101.652 (1)
V (Å³)	4009.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	21210, 4398, 3293
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.126, 1.03
No. of reflections	4398
No. of parameters	274
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C7/C8/C9 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3	0.82	1.88	2.6127 (17)	148
C12—H12···O1	0.93	2.33	3.004 (2)	130
C2—H2···O2ⁱ	0.93	2.48	3.267 (2)	142
C11—H11B···O1ⁱⁱ	0.96	2.36	3.309 (2)	172
C4—H4···Cg2ⁱⁱⁱ	0.93	2.89	3.746 (2)	153
C6—H6···Cg1^iv	0.93	2.78	3.559 (2)	142

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, y−1, z; (iii) x, −y, z+1/2; (iv) −x+1, y, −z+3/2.

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gursoy, A., Demirayak, S., Capan, G., Erol, K. & Vural, K. (2000). Eur. J. Med. Chem. 35, 359–364. Web of Science CrossRef PubMed CAS Google Scholar
Ragavan, R. V., Vijayakumar, V. & Kumari, N. S. (2009). Eur. J. Med. Chem. 44, 3852–3857. PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, L.-G., Zhang, C.-N., Yan, G.-B., Zheng, Y.-F. & Yang, M.-H. (2007). Acta Cryst. E63, o1245–o1246. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, Z.-F., Shen, X.-H. & Tang, X.-G. (2008). Acta Cryst. E64, o1965–o1966. Web of Science CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[(E)-(4-Di­ethyl­amino-2-hy­dr­oxy­benzyl­­idene)amino]-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

4-[(E)-(4-Diethylamino-2-hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one