1,5-Dimethyl-2-phenyl-4-[phenyl(pyri­din-2-ylamino)methyl]-1H-pyrazol-3(2H)-one

Krishnakumar, K.; Franklin, S.; Prabhu, G.V.; Balasubramanian, T.

doi:10.1107/S1600536812042936

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3193

doi:10.1107/S1600536812042936

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1,5-Dimethyl-2-phenyl-4-[phenyl(pyridin-2-ylamino)methyl]-1H-pyrazol-3(2H)-one

K. Krishnakumar,^a S. Franklin,^b ^* G. Venkatesa Prabhu ^a and T. Balasubramanian ^c

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, Tamilnadu, India, ^bDepartment of Physics, Bishop Heber College (Autonomous), Tiruchirappalli 620 017, Tamilnadu, India, and ^cDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, Tamilnadu, India
^*Correspondence e-mail: xrdfrank@yahoo.co.in

(Received 22 August 2012; accepted 15 October 2012; online 20 October 2012)

In the title compound, C₂₃H₂₂N₄O, the pyrazole ring makes dihedral angles of 45.57 (11)° with the attached phenyl ring, and 83.98 (10) and 67.85 (10) °, respectively, with the other phenyl ring and the pyridyl ring. The pyridyl ring makes a dihedral angle of 80.15 (10)° with the adjacent phenyl ring. In the crystal, N—H⋯O hydrogen bonds supplemented by weak C—H⋯O hydrogen bonds link the molecules into chains which run parallel to the a-axis direction.

Related literature

For the origin of the material studied, see: Vijayan (1971 ); Singh & Vijayan (1973 ). For related structures, see: Singh & Vijayan (1974 , 1976 ); Tordjman et al. (1991 ); Yadav et al. (2003 ); Li & Zhang (2004 ); Wen (2005 ); Sun et al. (2007 ).

Experimental

Crystal data

C₂₃H₂₂N₄O
M_r = 370.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.701 (5) Å
b = 12.485 (5) Å
c = 26.736 (5) Å
V = 1903.0 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.3 × 0.2 × 0.2 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.976, T_max = 0.984
14432 measured reflections
2959 independent reflections
2337 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.095
S = 1.01
2959 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.85 (3)	2.16 (3)	2.982 (3)	161 (2)
C18—H18⋯O1ⁱ	0.93	2.58	3.335 (3)	138
C23—H23C⋯O1ⁱⁱ	0.96	2.59	3.512 (3)	162
Symmetry codes: (i) x-1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042936/go2065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042936/go2065Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042936/go2065Isup3.cml

checkCIF report

Comment top

Antipyrine (2,3-dimethyl-1-phenylpyrazol-5-one) is one of the best known pyrazole derivatives used as pain-relieving medicine. It is the first pyrazole derivative to be introduced as an analgesic and antipyretic drug. Antipyrine and its derivatives have been long known for their wide spectrum of biological activities. Their roles in biological processes have become a topic of study in recent years. Though rarely used alone, nowadays, on account of its toxicity, antipyrine forms part of some combination products used as pain-relieving medicines. Many of its derivatives like amidopyrine and metamizol are well known and widely used analgesics. Therefore a detailed knowledge of the structure and the possible modes of interaction of antipyrine are important in elucidating the molecular mechanism of the action of pain-relieving medicines. The crystal structure of antipyrine, its derivatives and some of its metallic complexes have already been reported (see related literature). Presently, the crystal structure of 2-amino pyridino benzyl antipyrine {1,2-dihydro-2,3-dimethyl-1-phenyl-4-(phenyl (pyridin-2-yl amino) methyl)pyrazol-5-one} has been elucidated. The conformational features and the hydrogen bonding analysis have been analysed in order to have a further insight in to their chemical and pharmaceutical aspects. The chemical scheme of 2-amino pyridino benzyl antipyrine is shown.

An ORTEP-3 (Farrugia, 1997) diagram of the asymmetric unit of 2-amino pyridino benzyl antipyrine (APBA) is shown in Figure 1. In APBA, the antipyrine, benzene and pyridyl amine molecules are bridged by C10 which is the asymmetric sp3 carbon in the structure. Bond lengths and angles are comparable with those of the related structures reported. Four flat fragments are present in the structure elucidated. The dihedral angles between these flat rings A (C1—C6), B (N1, N2, C7—C9), C (C11—C16) and D (C17—C21, N4) are A/B= 45.57 (11)°, A/C= 54.96 (10)°, A/D= 82.10 (11)°, B/C= 83.98 (10)°, B/D= 67.85 (10)° and C/D= 80.15 (10)°. These values show that the pyrazole (B), benzene (C) and pyridyl (D) rings are almost perpendicular to each other. The crystal packing of the compound APBA is stabilized by N3–H3A···O1 and C18—H18···O1 hydrogen bonds which link the molecules into one-dimensional chains which run parallel to the a-axis, Table 1, Figure 2. In addition there is a short contact C23–H23C···O1.

Related literature top

For the origin of the material studied, see: Vijayan (1971); Singh & Vijayan (1973). For related structures, see: Singh & Vijayan (1974, 1976); Tordjman et al. (1991); Yadav et al. (2003); Li & Zhang (2004); Wen (2005); Sun et al. (2007).

Experimental top

5.31 mmol of 2-aminopyridine and 5.31 mmol of benzaldehyde were dissolved in ethanol solution. To this mixture 5.31 mmol of antipyrine was added and stirred well. The contents were refluxed at a temperature of 333 K for 12 h. The product obtained by Mannich base condensation was filtered, dried and then washed with distilled water. It is then dried in the air oven at 323 K. By slow evaporation technique, using ethanol, orange colour block shaped crystals of title compound suitable for X-ray diffraction analysis were obtained from the product.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of APBA, showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of APBA, showing the hydrogen bonding patterns. For the sake of clarity, only H atoms involved in hydrogen bonding are shown. Dashed lines represent hydrogen bonds.

1,5-Dimethyl-2-phenyl-4-[phenyl(pyridin-2-ylamino)methyl]-1H- pyrazol-3(2H)-one top

Crystal data top

C₂₃H₂₂N₄O	F(000) = 784
M_r = 370.45	D_x = 1.293 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3758 reflections
a = 5.701 (5) Å	θ = 2.2–25.4°
b = 12.485 (5) Å	µ = 0.08 mm⁻¹
c = 26.736 (5) Å	T = 273 K
V = 1903.0 (19) Å³	Block, orange
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2337 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scan	θ_max = 29.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −4→7
T_min = 0.976, T_max = 0.984	k = −17→17
14432 measured reflections	l = −36→34
2959 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0435P)² + 0.2362P] where P = (F_o² + 2F_c²)/3
2959 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₃H₂₂N₄O	V = 1903.0 (19) Å³
M_r = 370.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.701 (5) Å	µ = 0.08 mm⁻¹
b = 12.485 (5) Å	T = 273 K
c = 26.736 (5) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2959 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2337 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.036
14432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.18 e Å⁻³
2959 reflections	Δρ_min = −0.19 e Å⁻³
259 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.3555 (2)	0.08528 (11)	0.70108 (5)	0.0391 (3)
N1	0.2298 (3)	0.21846 (12)	0.75511 (6)	0.0315 (4)
N2	0.0380 (3)	0.28913 (12)	0.75618 (6)	0.0335 (4)
N3	−0.2190 (3)	0.08348 (13)	0.63621 (6)	0.0352 (4)
N4	−0.0868 (3)	−0.01040 (13)	0.56735 (6)	0.0396 (4)
C1	0.1607 (4)	0.17086 (18)	0.84215 (8)	0.0405 (5)
H1	0.0148	0.2041	0.8409	0.049*
C2	0.2324 (5)	0.11982 (18)	0.88527 (9)	0.0508 (6)
H2	0.1348	0.1191	0.9131	0.061*
C3	0.4462 (5)	0.0702 (2)	0.88728 (9)	0.0551 (7)
H3	0.492	0.0342	0.9161	0.066*
C4	0.5923 (5)	0.07368 (19)	0.84676 (9)	0.0505 (6)
H4	0.7383	0.0407	0.8484	0.061*
C5	0.5254 (4)	0.12577 (16)	0.80329 (9)	0.0409 (5)
H5	0.6266	0.1293	0.7761	0.049*
C6	0.3058 (4)	0.17246 (15)	0.80100 (7)	0.0325 (4)
C7	0.2224 (3)	0.16029 (14)	0.71041 (7)	0.0290 (4)
C8	0.0321 (3)	0.20467 (14)	0.68212 (7)	0.0280 (4)
C9	−0.0668 (4)	0.28329 (14)	0.71018 (7)	0.0313 (4)
C10	−0.0332 (3)	0.16209 (15)	0.63147 (7)	0.0298 (4)
H10	0.1045	0.1232	0.6192	0.036*
C11	−0.0829 (3)	0.25022 (15)	0.59317 (7)	0.0282 (4)
C12	−0.2876 (4)	0.25263 (16)	0.56545 (7)	0.0331 (4)
H12	−0.4044	0.2023	0.5715	0.04*
C13	−0.3200 (4)	0.32958 (17)	0.52860 (8)	0.0390 (5)
H13	−0.458	0.3303	0.51	0.047*
C14	−0.1491 (4)	0.40456 (17)	0.51947 (8)	0.0410 (5)
H14	−0.1703	0.4559	0.4947	0.049*
C15	0.0535 (4)	0.40313 (17)	0.54730 (8)	0.0420 (5)
H15	0.1691	0.4541	0.5414	0.05*
C16	0.0869 (4)	0.32708 (16)	0.58385 (7)	0.0355 (4)
H16	0.2247	0.3273	0.6025	0.043*
C17	−0.2525 (4)	0.00363 (14)	0.60187 (7)	0.0319 (4)
C18	−0.4543 (4)	−0.06045 (16)	0.60472 (8)	0.0400 (5)
H18	−0.5674	−0.0482	0.6291	0.048*
C19	−0.4802 (5)	−0.14120 (17)	0.57079 (9)	0.0497 (6)
H19	−0.6112	−0.1855	0.572	0.06*
C20	−0.3093 (5)	−0.15665 (18)	0.53444 (9)	0.0527 (7)
H20	−0.3239	−0.2107	0.5107	0.063*
C21	−0.1212 (5)	−0.09074 (17)	0.53461 (8)	0.0473 (6)
H21	−0.007	−0.1017	0.5103	0.057*
C22	−0.2613 (4)	0.35812 (17)	0.69792 (9)	0.0460 (6)
H22A	−0.1975	0.4263	0.6884	0.069*
H22B	−0.36	0.367	0.7267	0.069*
H22C	−0.3518	0.3294	0.6708	0.069*
C23	0.0838 (5)	0.39199 (16)	0.78084 (9)	0.0508 (6)
H23A	0.1981	0.4314	0.762	0.076*
H23B	0.1424	0.3794	0.814	0.076*
H23C	−0.0591	0.4325	0.7827	0.076*
H3A	−0.332 (5)	0.0995 (19)	0.6557 (9)	0.049 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0394 (8)	0.0403 (8)	0.0375 (8)	0.0110 (7)	0.0007 (7)	−0.0041 (6)
N1	0.0361 (9)	0.0307 (8)	0.0278 (9)	0.0034 (7)	−0.0035 (7)	−0.0019 (6)
N2	0.0436 (9)	0.0287 (8)	0.0283 (9)	0.0074 (7)	−0.0037 (7)	−0.0045 (6)
N3	0.0436 (10)	0.0328 (8)	0.0292 (9)	−0.0055 (8)	0.0075 (8)	−0.0056 (7)
N4	0.0508 (11)	0.0353 (9)	0.0327 (9)	0.0003 (9)	0.0028 (9)	−0.0044 (7)
C1	0.0454 (12)	0.0427 (11)	0.0335 (12)	−0.0056 (10)	−0.0035 (10)	0.0010 (9)
C2	0.0648 (16)	0.0552 (14)	0.0323 (12)	−0.0131 (14)	−0.0021 (12)	0.0063 (10)
C3	0.0689 (17)	0.0550 (14)	0.0414 (14)	−0.0137 (14)	−0.0234 (13)	0.0140 (11)
C4	0.0433 (13)	0.0489 (14)	0.0594 (16)	−0.0064 (11)	−0.0209 (12)	0.0106 (11)
C5	0.0359 (11)	0.0433 (12)	0.0434 (13)	−0.0057 (9)	−0.0056 (10)	0.0067 (9)
C6	0.0388 (11)	0.0305 (9)	0.0283 (10)	−0.0070 (8)	−0.0088 (9)	0.0000 (7)
C7	0.0328 (10)	0.0284 (9)	0.0257 (10)	−0.0024 (8)	0.0024 (8)	−0.0005 (7)
C8	0.0337 (10)	0.0271 (9)	0.0232 (9)	−0.0015 (8)	0.0000 (7)	0.0007 (7)
C9	0.0390 (10)	0.0279 (9)	0.0269 (10)	0.0009 (8)	−0.0015 (8)	0.0018 (7)
C10	0.0334 (9)	0.0310 (9)	0.0248 (9)	−0.0008 (8)	0.0008 (8)	−0.0026 (7)
C11	0.0338 (9)	0.0309 (9)	0.0200 (9)	0.0000 (8)	0.0012 (8)	−0.0035 (7)
C12	0.0328 (10)	0.0361 (9)	0.0305 (11)	−0.0005 (9)	−0.0017 (8)	−0.0032 (8)
C13	0.0420 (12)	0.0446 (11)	0.0304 (11)	0.0070 (10)	−0.0078 (9)	−0.0045 (9)
C14	0.0567 (14)	0.0375 (11)	0.0288 (11)	0.0090 (11)	0.0039 (10)	0.0052 (8)
C15	0.0476 (13)	0.0390 (11)	0.0396 (12)	−0.0055 (11)	0.0071 (10)	0.0057 (9)
C16	0.0335 (10)	0.0400 (11)	0.0330 (11)	−0.0036 (9)	−0.0023 (8)	0.0006 (8)
C17	0.0415 (10)	0.0263 (9)	0.0278 (10)	0.0024 (8)	−0.0037 (8)	0.0026 (7)
C18	0.0429 (12)	0.0348 (10)	0.0423 (13)	−0.0010 (9)	−0.0038 (10)	0.0007 (8)
C19	0.0548 (14)	0.0384 (12)	0.0558 (15)	−0.0077 (11)	−0.0115 (13)	−0.0040 (10)
C20	0.0776 (18)	0.0353 (11)	0.0452 (14)	0.0009 (13)	−0.0092 (13)	−0.0140 (10)
C21	0.0679 (16)	0.0385 (11)	0.0354 (12)	0.0068 (12)	0.0022 (11)	−0.0090 (9)
C22	0.0517 (13)	0.0461 (12)	0.0403 (13)	0.0179 (11)	−0.0038 (11)	−0.0047 (9)
C23	0.0748 (17)	0.0324 (11)	0.0452 (13)	0.0050 (12)	−0.0110 (13)	−0.0129 (9)

Geometric parameters (Å, º) top

O1—C7	1.231 (2)	C10—H10	0.98
N1—C7	1.399 (2)	C11—C12	1.383 (3)
N1—N2	1.405 (2)	C11—C16	1.386 (3)
N1—C6	1.422 (2)	C12—C13	1.389 (3)
N2—C9	1.369 (2)	C12—H12	0.93
N2—C23	1.467 (2)	C13—C14	1.373 (3)
N3—C17	1.369 (2)	C13—H13	0.93
N3—C10	1.450 (3)	C14—C15	1.374 (3)
N3—H3A	0.85 (3)	C14—H14	0.93
N4—C17	1.332 (3)	C15—C16	1.376 (3)
N4—C21	1.346 (3)	C15—H15	0.93
C1—C6	1.377 (3)	C16—H16	0.93
C1—C2	1.379 (3)	C17—C18	1.403 (3)
C1—H1	0.93	C18—C19	1.364 (3)
C2—C3	1.368 (4)	C18—H18	0.93
C2—H2	0.93	C19—C20	1.390 (4)
C3—C4	1.367 (4)	C19—H19	0.93
C3—H3	0.93	C20—C21	1.352 (4)
C4—C5	1.385 (3)	C20—H20	0.93
C4—H4	0.93	C21—H21	0.93
C5—C6	1.382 (3)	C22—H22A	0.96
C5—H5	0.93	C22—H22B	0.96
C7—C8	1.434 (3)	C22—H22C	0.96
C8—C9	1.358 (3)	C23—H23A	0.96
C8—C10	1.502 (3)	C23—H23B	0.96
C9—C22	1.486 (3)	C23—H23C	0.96
C10—C11	1.530 (3)

C7—N1—N2	108.65 (15)	C12—C11—C10	122.07 (17)
C7—N1—C6	122.45 (15)	C16—C11—C10	119.27 (17)
N2—N1—C6	118.22 (16)	C11—C12—C13	120.52 (19)
C9—N2—N1	106.73 (15)	C11—C12—H12	119.7
C9—N2—C23	121.87 (16)	C13—C12—H12	119.7
N1—N2—C23	114.84 (18)	C14—C13—C12	120.2 (2)
C17—N3—C10	122.43 (17)	C14—C13—H13	119.9
C17—N3—H3A	118.4 (17)	C12—C13—H13	119.9
C10—N3—H3A	116.5 (17)	C13—C14—C15	119.4 (2)
C17—N4—C21	116.5 (2)	C13—C14—H14	120.3
C6—C1—C2	119.8 (2)	C15—C14—H14	120.3
C6—C1—H1	120.1	C14—C15—C16	120.7 (2)
C2—C1—H1	120.1	C14—C15—H15	119.7
C3—C2—C1	120.4 (2)	C16—C15—H15	119.7
C3—C2—H2	119.8	C15—C16—C11	120.6 (2)
C1—C2—H2	119.8	C15—C16—H16	119.7
C4—C3—C2	119.8 (2)	C11—C16—H16	119.7
C4—C3—H3	120.1	N4—C17—N3	117.50 (19)
C2—C3—H3	120.1	N4—C17—C18	122.95 (18)
C3—C4—C5	120.8 (2)	N3—C17—C18	119.54 (19)
C3—C4—H4	119.6	C19—C18—C17	118.3 (2)
C5—C4—H4	119.6	C19—C18—H18	120.9
C6—C5—C4	119.0 (2)	C17—C18—H18	120.9
C6—C5—H5	120.5	C18—C19—C20	119.4 (2)
C4—C5—H5	120.5	C18—C19—H19	120.3
C1—C6—C5	120.20 (19)	C20—C19—H19	120.3
C1—C6—N1	120.80 (19)	C21—C20—C19	118.0 (2)
C5—C6—N1	118.96 (19)	C21—C20—H20	121
O1—C7—N1	123.31 (17)	C19—C20—H20	121
O1—C7—C8	130.83 (18)	N4—C21—C20	124.9 (2)
N1—C7—C8	105.83 (16)	N4—C21—H21	117.6
C9—C8—C7	107.59 (17)	C20—C21—H21	117.6
C9—C8—C10	130.63 (19)	C9—C22—H22A	109.5
C7—C8—C10	121.76 (17)	C9—C22—H22B	109.5
C8—C9—N2	110.70 (17)	H22A—C22—H22B	109.5
C8—C9—C22	129.95 (19)	C9—C22—H22C	109.5
N2—C9—C22	119.35 (17)	H22A—C22—H22C	109.5
N3—C10—C8	109.99 (15)	H22B—C22—H22C	109.5
N3—C10—C11	114.21 (16)	N2—C23—H23A	109.5
C8—C10—C11	113.27 (15)	N2—C23—H23B	109.5
N3—C10—H10	106.2	H23A—C23—H23B	109.5
C8—C10—H10	106.2	N2—C23—H23C	109.5
C11—C10—H10	106.2	H23A—C23—H23C	109.5
C12—C11—C16	118.57 (18)	H23B—C23—H23C	109.5

C7—N1—N2—C9	−7.28 (19)	N1—N2—C9—C22	−173.48 (17)
C6—N1—N2—C9	−152.75 (17)	C23—N2—C9—C22	−38.8 (3)
C7—N1—N2—C23	−145.59 (17)	C17—N3—C10—C8	−154.18 (18)
C6—N1—N2—C23	68.9 (2)	C17—N3—C10—C11	77.2 (2)
C6—C1—C2—C3	−0.4 (3)	C9—C8—C10—N3	−83.2 (2)
C1—C2—C3—C4	1.7 (4)	C7—C8—C10—N3	94.7 (2)
C2—C3—C4—C5	−0.8 (4)	C9—C8—C10—C11	46.0 (3)
C3—C4—C5—C6	−1.4 (3)	C7—C8—C10—C11	−136.16 (18)
C2—C1—C6—C5	−1.8 (3)	N3—C10—C11—C12	−0.6 (2)
C2—C1—C6—N1	175.87 (19)	C8—C10—C11—C12	−127.61 (19)
C4—C5—C6—C1	2.7 (3)	N3—C10—C11—C16	−177.14 (17)
C4—C5—C6—N1	−175.04 (19)	C8—C10—C11—C16	55.9 (2)
C7—N1—C6—C1	−121.8 (2)	C16—C11—C12—C13	0.9 (3)
N2—N1—C6—C1	18.7 (3)	C10—C11—C12—C13	−175.58 (18)
C7—N1—C6—C5	55.9 (3)	C11—C12—C13—C14	−0.3 (3)
N2—N1—C6—C5	−163.60 (16)	C12—C13—C14—C15	−0.4 (3)
N2—N1—C7—O1	−173.02 (17)	C13—C14—C15—C16	0.4 (3)
C6—N1—C7—O1	−29.3 (3)	C14—C15—C16—C11	0.2 (3)
N2—N1—C7—C8	5.19 (19)	C12—C11—C16—C15	−0.9 (3)
C6—N1—C7—C8	148.89 (17)	C10—C11—C16—C15	175.72 (18)
O1—C7—C8—C9	176.9 (2)	C21—N4—C17—N3	178.70 (18)
N1—C7—C8—C9	−1.2 (2)	C21—N4—C17—C18	−0.2 (3)
O1—C7—C8—C10	−1.4 (3)	C10—N3—C17—N4	10.0 (3)
N1—C7—C8—C10	−179.44 (16)	C10—N3—C17—C18	−171.04 (18)
C7—C8—C9—N2	−3.4 (2)	N4—C17—C18—C19	0.6 (3)
C10—C8—C9—N2	174.63 (18)	N3—C17—C18—C19	−178.4 (2)
C7—C8—C9—C22	176.7 (2)	C17—C18—C19—C20	−0.8 (3)
C10—C8—C9—C22	−5.2 (4)	C18—C19—C20—C21	0.7 (4)
N1—N2—C9—C8	6.6 (2)	C17—N4—C21—C20	0.1 (3)
C23—N2—C9—C8	141.4 (2)	C19—C20—C21—N4	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.85 (3)	2.16 (3)	2.982 (3)	161 (2)
C18—H18···O1ⁱ	0.93	2.58	3.335 (3)	138
C23—H23C···O1ⁱⁱ	0.96	2.59	3.512 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₄O
M_r	370.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	5.701 (5), 12.485 (5), 26.736 (5)
V (Å³)	1903.0 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14432, 2959, 2337
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.095, 1.01
No. of reflections	2959
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.85 (3)	2.16 (3)	2.982 (3)	161 (2)
C18—H18···O1ⁱ	0.93	2.58	3.335 (3)	138
C23—H23C···O1ⁱⁱ	0.96	2.59	3.512 (3)	162

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

Acknowledgements

The authors thank the SAIF at IITM Chennai, sponsored by DST India, for providing analytical facilities.

References

Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 68| Part 11| November 2012| Page o3193

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

1,5-Di­methyl-2-phenyl-4-[phenyl(pyri­din-2-ylamino)methyl]-1H-pyrazol-3(2H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Dimethyl-2-phenyl-4-[phenyl(pyridin-2-ylamino)methyl]-1H-pyrazol-3(2H)-one