4-[(4-Chloro­phen­yl)(5-hydr­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Fun, H.-K.; Jebas, S.R.; Girish, K.S.; Kalluraya, B.

doi:10.1107/S1600536808036088

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages o2301-o2302

doi:10.1107/S1600536808036088

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4-[(4-Chlorophenyl)(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ K. S. Girish ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 October 2008; accepted 4 November 2008; online 8 November 2008)

In the the title compound, C₂₇H₂₃ClN₄O₂, the chlorophenyl ring forms dihedral angles of 77.70 (9) and 86.65 (9)°, respectively, with the pyrazol-3-one and pyrazole rings. The phenyl rings attached to the pyrazole rings are twisted away from them [dihedral angles 33.80 (9) and 40.34 (10)°]. An intramolecular O—H⋯O hydrogen bond generates an S(8) ring motif. The molecules are linked into chains running along the c axis by N—H⋯N hydrogen bonds, and the chains are cross-linked via C—H⋯O hydrogen bonds and C—H⋯π interactions involving the chlorophenyl ring.

Related literature

For the biological activities of pyrazoles, see: Burger & Iorio (1979 ); Holla et al. (1994 ); Kalluraya & Chimbalkar (2001 ); Windholz (1976 ); Wolff (1980 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₇H₂₃ClN₄O₂
M_r = 470.94
Monoclinic, P 2₁ /c
a = 10.8809 (2) Å
b = 11.2046 (2) Å
c = 18.9376 (3) Å
β = 97.994 (1)°
V = 2286.36 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100.0 (1) K
0.41 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.923, T_max = 0.987
26858 measured reflections
6751 independent reflections
4614 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.121
S = 1.02
6751 reflections
317 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.83 (1)	1.67 (1)	2.5025 (17)	176 (3)
N2—H1N2⋯N3ⁱ	0.86 (1)	1.90 (1)	2.7544 (19)	174 (2)
C13—H13A⋯O2ⁱⁱ	0.95	2.58	3.375 (2)	142
C4—H4A⋯Cg1ⁱⁱⁱ	0.95	2.67	3.5088 (18)	147
C24—H24A⋯Cg1^iv	0.95	2.86	3.745 (2)	155
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z; (iv) -x+1, -y, -z+1. Cg1 is the centroid of the C11–C16 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036088/ci2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036088/ci2705Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives have been reported to posses various biological activities such as anti-inflammatory (Windholz, 1976), analgesic, hypoglycemic (Wolff, 1980), sedative and hypnotics (Burger & Iorio, 1979), antifungal and antibacterial (Kalluraya & Chimbalkar, 2001) activities. Propenones are also found to show good antibacterial activity (Holla et al., 1994). Prompted by the pharmacological applications of propenones and pyrazole derivatives, we synthesized the title compound containing the propenone-pyrazole moiety and report here its crystal structure.

Bond lengths in the title molecule (Fig.1) have normal values (Allen et al., 1987). The chlorophenyl ring (C11—C16) forms dihedral angles of 77.70 (9)° and 86.65 (9)°, respectively, with the N1/N2/C7—C9 and N3/N4/C17—C19 pyrazole rings. The phenyl rings attached to the pyrazole rings are twisted; the dihedral angle between the C1—C6 and N1/N2/C7—C9 rings is 33.80 (9)° and that between C20—C25 and N3/N4/C17—C19 rings is 40.34 (10)°. An intramolecular O—H···O hydrogen bond generates an S(8) ring motif (Bernstein et al., 1995).

The crystal packing shows that the molecules are linked into chains running along the c axis (Fig.2) by N—H···N hydrogen bonds (Table 1). The chains are cross-linked via C—H···O hydrogen bonds and C—H···π interactions (Table 1) involving the C11—C16 benzene ring (centroid Cg1).

Related literature top

For the biological activities of pyrazoles, see: Burger & Iorio (1979); Holla et al. (1994); Kalluraya & Chimbalkar (2001); Windholz (1976); Wolff (1980). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by the direct fusion of 1-phenyl-3-methyl 5-pyrazolone (0.1 mole) with p-chlorobenzaldehyde (0.1 mole) at 413 K for 3 h. The reaction mixture was cooled to room temperature and stirred with methanol using a glass rod. The mixture was then filtered to obtain a solid product. Single crystals suitable for X-ray analysis were obtained by recrystallization from ethanol under slow evaporation (m.p. 351–353 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonding.

4-[(4-Chlorophenyl)(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl]- 5-methyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₇H₂₃ClN₄O₂	F(000) = 984
M_r = 470.94	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3311 reflections
a = 10.8809 (2) Å	θ = 2.6–26.3°
b = 11.2046 (2) Å	µ = 0.20 mm⁻¹
c = 18.9376 (3) Å	T = 100 K
β = 97.994 (1)°	Plate, colourless
V = 2286.36 (7) Å³	0.41 × 0.13 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6751 independent reflections
Radiation source: fine-focus sealed tube	4614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→13
T_min = 0.923, T_max = 0.987	k = −15→15
26858 measured reflections	l = −26→26

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0491P)² + 0.4127P] where P = (F_o² + 2F_c²)/3
6751 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.46 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₇H₂₃ClN₄O₂	V = 2286.36 (7) Å³
M_r = 470.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8809 (2) Å	µ = 0.20 mm⁻¹
b = 11.2046 (2) Å	T = 100 K
c = 18.9376 (3) Å	0.41 × 0.13 × 0.07 mm
β = 97.994 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6751 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4614 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.987	R_int = 0.072
26858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	2 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.46 e Å⁻³
6751 reflections	Δρ_min = −0.36 e Å⁻³
317 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	0.01004 (4)	0.17798 (4)	0.21608 (3)	0.02610 (12)
O1	0.64039 (12)	−0.00053 (10)	0.20712 (6)	0.0164 (3)
O2	0.73070 (12)	−0.10345 (11)	0.31975 (6)	0.0177 (3)
N1	0.60775 (13)	−0.11487 (12)	0.10350 (7)	0.0145 (3)
N2	0.53262 (14)	−0.20840 (13)	0.07833 (7)	0.0156 (3)
N3	0.54617 (13)	−0.18017 (13)	0.44999 (7)	0.0156 (3)
N4	0.65437 (14)	−0.14862 (13)	0.42469 (7)	0.0153 (3)
C1	0.79797 (17)	−0.01062 (16)	0.08926 (9)	0.0185 (4)
H1A	0.8241	−0.0179	0.1391	0.022*
C2	0.87259 (17)	0.04719 (17)	0.04601 (10)	0.0215 (4)
H2A	0.9493	0.0813	0.0665	0.026*
C3	0.83517 (18)	0.05518 (16)	−0.02710 (10)	0.0217 (4)
H3A	0.8863	0.0945	−0.0566	0.026*
C4	0.72305 (18)	0.00560 (16)	−0.05690 (9)	0.0191 (4)
H4A	0.6986	0.0094	−0.1070	0.023*
C5	0.64626 (17)	−0.04955 (15)	−0.01398 (9)	0.0169 (4)
H5A	0.5683	−0.0814	−0.0342	0.020*
C6	0.68519 (16)	−0.05749 (15)	0.05896 (9)	0.0144 (3)
C7	0.58670 (16)	−0.08704 (15)	0.17178 (8)	0.0138 (3)
C8	0.49935 (15)	−0.17256 (14)	0.18995 (8)	0.0125 (3)
C9	0.46835 (16)	−0.24398 (15)	0.13014 (8)	0.0139 (3)
C10	0.43446 (15)	−0.17598 (15)	0.25589 (8)	0.0129 (3)
H10A	0.3941	−0.2562	0.2553	0.015*
C11	0.32806 (16)	−0.08614 (15)	0.24690 (8)	0.0138 (3)
C12	0.34955 (17)	0.03621 (15)	0.25601 (9)	0.0165 (3)
H12A	0.4319	0.0640	0.2696	0.020*
C13	0.25287 (17)	0.11770 (16)	0.24563 (9)	0.0181 (4)
H13A	0.2686	0.2007	0.2516	0.022*
C14	0.13238 (17)	0.07611 (16)	0.22627 (9)	0.0176 (4)
C15	0.10766 (17)	−0.04447 (17)	0.21678 (9)	0.0194 (4)
H15A	0.0250	−0.0719	0.2036	0.023*
C16	0.20633 (16)	−0.12484 (16)	0.22686 (9)	0.0166 (4)
H16A	0.1904	−0.2077	0.2199	0.020*
C17	0.51224 (16)	−0.16574 (14)	0.32860 (8)	0.0131 (3)
C18	0.46196 (16)	−0.19106 (15)	0.39214 (9)	0.0149 (3)
C19	0.63540 (16)	−0.13831 (15)	0.35195 (9)	0.0142 (3)
C20	0.76611 (17)	−0.13465 (16)	0.47292 (9)	0.0166 (4)
C21	0.87757 (18)	−0.17791 (17)	0.45591 (10)	0.0220 (4)
H21A	0.8809	−0.2158	0.4113	0.026*
C22	0.98413 (19)	−0.16538 (18)	0.50458 (11)	0.0272 (4)
H22A	1.0609	−0.1946	0.4931	0.033*
C23	0.9802 (2)	−0.11074 (19)	0.56995 (11)	0.0304 (5)
H23A	1.0538	−0.1025	0.6030	0.037*
C24	0.8685 (2)	−0.06834 (19)	0.58662 (10)	0.0282 (5)
H24A	0.8654	−0.0314	0.6315	0.034*
C25	0.76066 (18)	−0.07926 (17)	0.53833 (9)	0.0217 (4)
H25A	0.6841	−0.0494	0.5497	0.026*
C26	0.37668 (17)	−0.34251 (16)	0.11547 (9)	0.0195 (4)
H26A	0.4083	−0.4019	0.0845	0.029*
H26B	0.2979	−0.3103	0.0917	0.029*
H26C	0.3635	−0.3803	0.1605	0.029*
C27	0.33330 (17)	−0.23080 (17)	0.39909 (9)	0.0198 (4)
H27A	0.3299	−0.2573	0.4481	0.030*
H27B	0.3099	−0.2970	0.3661	0.030*
H27C	0.2756	−0.1642	0.3876	0.030*
H1N2	0.541 (2)	−0.2396 (19)	0.0380 (7)	0.037 (7)*
H1O2	0.702 (2)	−0.066 (2)	0.2832 (9)	0.057 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0214 (2)	0.0300 (3)	0.0268 (2)	0.0090 (2)	0.00288 (18)	−0.0010 (2)
O1	0.0231 (7)	0.0152 (6)	0.0111 (6)	−0.0047 (5)	0.0031 (5)	−0.0009 (5)
O2	0.0190 (7)	0.0226 (7)	0.0120 (6)	−0.0015 (5)	0.0034 (5)	0.0031 (5)
N1	0.0187 (8)	0.0152 (7)	0.0100 (7)	−0.0037 (6)	0.0032 (6)	−0.0012 (5)
N2	0.0206 (8)	0.0166 (7)	0.0102 (7)	−0.0027 (6)	0.0042 (6)	−0.0034 (5)
N3	0.0179 (7)	0.0178 (7)	0.0119 (7)	0.0001 (6)	0.0049 (5)	0.0015 (6)
N4	0.0181 (8)	0.0180 (7)	0.0099 (7)	−0.0006 (6)	0.0019 (6)	0.0016 (5)
C1	0.0184 (9)	0.0245 (9)	0.0127 (8)	0.0018 (7)	0.0027 (7)	0.0006 (7)
C2	0.0183 (9)	0.0264 (10)	0.0208 (9)	−0.0015 (8)	0.0062 (7)	−0.0010 (8)
C3	0.0250 (10)	0.0218 (9)	0.0210 (9)	0.0004 (8)	0.0124 (8)	0.0024 (7)
C4	0.0253 (10)	0.0216 (9)	0.0114 (8)	0.0039 (8)	0.0062 (7)	0.0028 (7)
C5	0.0178 (9)	0.0191 (9)	0.0136 (8)	0.0014 (7)	0.0021 (7)	−0.0002 (7)
C6	0.0166 (9)	0.0163 (8)	0.0114 (8)	0.0015 (7)	0.0057 (6)	0.0015 (6)
C7	0.0176 (9)	0.0149 (8)	0.0093 (7)	0.0035 (7)	0.0026 (6)	0.0011 (6)
C8	0.0149 (8)	0.0135 (7)	0.0091 (7)	0.0009 (7)	0.0020 (6)	0.0006 (6)
C9	0.0162 (8)	0.0148 (8)	0.0109 (7)	0.0020 (7)	0.0027 (6)	0.0017 (6)
C10	0.0159 (8)	0.0126 (8)	0.0106 (7)	−0.0022 (7)	0.0033 (6)	0.0007 (6)
C11	0.0172 (9)	0.0178 (8)	0.0070 (7)	0.0003 (7)	0.0039 (6)	0.0009 (6)
C12	0.0165 (9)	0.0179 (8)	0.0150 (8)	−0.0022 (7)	0.0018 (7)	0.0000 (7)
C13	0.0210 (9)	0.0168 (8)	0.0172 (8)	0.0003 (7)	0.0046 (7)	−0.0003 (7)
C14	0.0175 (9)	0.0224 (9)	0.0132 (8)	0.0051 (7)	0.0033 (7)	0.0010 (7)
C15	0.0143 (9)	0.0251 (9)	0.0189 (9)	−0.0019 (7)	0.0026 (7)	0.0000 (7)
C16	0.0195 (9)	0.0174 (8)	0.0133 (8)	−0.0026 (7)	0.0037 (7)	−0.0001 (6)
C17	0.0173 (8)	0.0133 (8)	0.0092 (7)	0.0008 (7)	0.0035 (6)	0.0007 (6)
C18	0.0190 (9)	0.0142 (8)	0.0116 (7)	0.0005 (7)	0.0030 (6)	0.0000 (6)
C19	0.0199 (9)	0.0129 (8)	0.0106 (7)	0.0012 (7)	0.0043 (6)	0.0003 (6)
C20	0.0201 (9)	0.0174 (8)	0.0114 (8)	−0.0011 (7)	−0.0008 (7)	0.0025 (6)
C21	0.0244 (10)	0.0213 (9)	0.0197 (9)	0.0043 (8)	0.0013 (7)	−0.0014 (7)
C22	0.0247 (10)	0.0277 (10)	0.0280 (10)	0.0033 (9)	−0.0003 (8)	0.0049 (8)
C23	0.0280 (11)	0.0364 (12)	0.0237 (10)	−0.0040 (9)	−0.0078 (8)	0.0058 (9)
C24	0.0329 (12)	0.0381 (12)	0.0125 (9)	−0.0084 (10)	−0.0008 (8)	−0.0003 (8)
C25	0.0244 (10)	0.0256 (10)	0.0154 (9)	−0.0008 (8)	0.0043 (7)	0.0005 (7)
C26	0.0232 (10)	0.0211 (9)	0.0140 (8)	−0.0055 (8)	0.0021 (7)	−0.0014 (7)
C27	0.0220 (10)	0.0260 (9)	0.0120 (8)	−0.0021 (8)	0.0046 (7)	0.0036 (7)

Geometric parameters (Å, º) top

Cl1—C14	1.7437 (18)	C11—C16	1.395 (2)
O1—C7	1.273 (2)	C11—C12	1.397 (2)
O2—C19	1.333 (2)	C12—C13	1.386 (2)
O2—H1O2	0.832 (10)	C12—H12A	0.95
N1—N2	1.3732 (19)	C13—C14	1.392 (2)
N1—C7	1.380 (2)	C13—H13A	0.95
N1—C6	1.426 (2)	C14—C15	1.384 (3)
N2—C9	1.342 (2)	C15—C16	1.394 (2)
N2—H1N2	0.856 (9)	C15—H15A	0.95
N3—C18	1.333 (2)	C16—H16A	0.95
N3—N4	1.3775 (19)	C17—C19	1.386 (2)
N4—C19	1.369 (2)	C17—C18	1.418 (2)
N4—C20	1.424 (2)	C18—C27	1.492 (2)
C1—C6	1.384 (2)	C20—C21	1.385 (3)
C1—C2	1.391 (2)	C20—C25	1.394 (2)
C1—H1A	0.95	C21—C22	1.384 (3)
C2—C3	1.391 (3)	C21—H21A	0.95
C2—H2A	0.95	C22—C23	1.387 (3)
C3—C4	1.387 (3)	C22—H22A	0.95
C3—H3A	0.95	C23—C24	1.382 (3)
C4—C5	1.389 (2)	C23—H23A	0.95
C4—H4A	0.95	C24—C25	1.389 (3)
C5—C6	1.390 (2)	C24—H24A	0.95
C5—H5A	0.95	C25—H25A	0.95
C7—C8	1.425 (2)	C26—H26A	0.98
C8—C9	1.389 (2)	C26—H26B	0.98
C8—C10	1.518 (2)	C26—H26C	0.98
C9—C26	1.488 (2)	C27—H27A	0.98
C10—C17	1.517 (2)	C27—H27B	0.98
C10—C11	1.526 (2)	C27—H27C	0.98
C10—H10A	1.00

C19—O2—H1O2	107.5 (19)	C12—C13—H13A	120.5
N2—N1—C7	109.22 (13)	C14—C13—H13A	120.5
N2—N1—C6	120.74 (13)	C15—C14—C13	121.32 (16)
C7—N1—C6	129.89 (14)	C15—C14—Cl1	119.53 (14)
C9—N2—N1	108.57 (13)	C13—C14—Cl1	119.13 (14)
C9—N2—H1N2	131.3 (15)	C14—C15—C16	118.73 (17)
N1—N2—H1N2	119.4 (15)	C14—C15—H15A	120.6
C18—N3—N4	105.11 (13)	C16—C15—H15A	120.6
C19—N4—N3	110.79 (14)	C15—C16—C11	121.36 (16)
C19—N4—C20	129.18 (15)	C15—C16—H16A	119.3
N3—N4—C20	120.00 (13)	C11—C16—H16A	119.3
C6—C1—C2	119.28 (16)	C19—C17—C18	104.10 (14)
C6—C1—H1A	120.4	C19—C17—C10	134.34 (15)
C2—C1—H1A	120.4	C18—C17—C10	121.51 (15)
C3—C2—C1	120.14 (17)	N3—C18—C17	112.15 (15)
C3—C2—H2A	119.9	N3—C18—C27	120.06 (15)
C1—C2—H2A	119.9	C17—C18—C27	127.74 (15)
C4—C3—C2	119.90 (16)	O2—C19—N4	117.85 (15)
C4—C3—H3A	120.1	O2—C19—C17	134.30 (15)
C2—C3—H3A	120.1	N4—C19—C17	107.82 (14)
C3—C4—C5	120.44 (16)	C21—C20—C25	120.61 (17)
C3—C4—H4A	119.8	C21—C20—N4	120.64 (16)
C5—C4—H4A	119.8	C25—C20—N4	118.73 (16)
C4—C5—C6	119.01 (17)	C22—C21—C20	119.29 (18)
C4—C5—H5A	120.5	C22—C21—H21A	120.4
C6—C5—H5A	120.5	C20—C21—H21A	120.4
C1—C6—C5	121.18 (16)	C21—C22—C23	120.80 (19)
C1—C6—N1	119.26 (15)	C21—C22—H22A	119.6
C5—C6—N1	119.56 (15)	C23—C22—H22A	119.6
O1—C7—N1	122.74 (15)	C24—C23—C22	119.54 (19)
O1—C7—C8	131.14 (15)	C24—C23—H23A	120.2
N1—C7—C8	106.11 (14)	C22—C23—H23A	120.2
C9—C8—C7	106.55 (14)	C23—C24—C25	120.58 (19)
C9—C8—C10	124.61 (15)	C23—C24—H24A	119.7
C7—C8—C10	128.14 (14)	C25—C24—H24A	119.7
N2—C9—C8	109.43 (15)	C24—C25—C20	119.19 (18)
N2—C9—C26	119.19 (15)	C24—C25—H25A	120.4
C8—C9—C26	131.30 (15)	C20—C25—H25A	120.4
C17—C10—C8	118.70 (14)	C9—C26—H26A	109.5
C17—C10—C11	111.73 (13)	C9—C26—H26B	109.5
C8—C10—C11	108.91 (13)	H26A—C26—H26B	109.5
C17—C10—H10A	105.5	C9—C26—H26C	109.5
C8—C10—H10A	105.5	H26A—C26—H26C	109.5
C11—C10—H10A	105.5	H26B—C26—H26C	109.5
C16—C11—C12	118.34 (16)	C18—C27—H27A	109.5
C16—C11—C10	120.15 (15)	C18—C27—H27B	109.5
C12—C11—C10	121.48 (15)	H27A—C27—H27B	109.5
C13—C12—C11	121.21 (17)	C18—C27—H27C	109.5
C13—C12—H12A	119.4	H27A—C27—H27C	109.5
C11—C12—H12A	119.4	H27B—C27—H27C	109.5
C12—C13—C14	119.04 (16)

C7—N1—N2—C9	−2.66 (18)	C10—C11—C12—C13	178.00 (15)
C6—N1—N2—C9	−178.76 (15)	C11—C12—C13—C14	0.5 (3)
C18—N3—N4—C19	1.09 (18)	C12—C13—C14—C15	−0.5 (3)
C18—N3—N4—C20	−177.23 (15)	C12—C13—C14—Cl1	177.88 (13)
C6—C1—C2—C3	−1.5 (3)	C13—C14—C15—C16	−0.1 (3)
C1—C2—C3—C4	0.1 (3)	Cl1—C14—C15—C16	−178.44 (13)
C2—C3—C4—C5	1.6 (3)	C14—C15—C16—C11	0.7 (3)
C3—C4—C5—C6	−1.9 (3)	C12—C11—C16—C15	−0.7 (2)
C2—C1—C6—C5	1.1 (3)	C10—C11—C16—C15	−178.61 (15)
C2—C1—C6—N1	−178.90 (16)	C8—C10—C17—C19	9.7 (3)
C4—C5—C6—C1	0.6 (3)	C11—C10—C17—C19	−118.3 (2)
C4—C5—C6—N1	−179.41 (15)	C8—C10—C17—C18	−167.66 (15)
N2—N1—C6—C1	−147.80 (16)	C11—C10—C17—C18	64.3 (2)
C7—N1—C6—C1	37.0 (3)	N4—N3—C18—C17	−0.72 (19)
N2—N1—C6—C5	32.2 (2)	N4—N3—C18—C27	176.97 (15)
C7—N1—C6—C5	−142.99 (18)	C19—C17—C18—N3	0.11 (19)
N2—N1—C7—O1	−177.20 (15)	C10—C17—C18—N3	178.15 (15)
C6—N1—C7—O1	−1.6 (3)	C19—C17—C18—C27	−177.37 (17)
N2—N1—C7—C8	3.27 (18)	C10—C17—C18—C27	0.7 (3)
C6—N1—C7—C8	178.90 (16)	N3—N4—C19—O2	177.35 (14)
O1—C7—C8—C9	177.87 (17)	C20—N4—C19—O2	−4.5 (3)
N1—C7—C8—C9	−2.66 (18)	N3—N4—C19—C17	−1.05 (19)
O1—C7—C8—C10	7.1 (3)	C20—N4—C19—C17	177.07 (16)
N1—C7—C8—C10	−173.38 (15)	C18—C17—C19—O2	−177.46 (18)
N1—N2—C9—C8	0.91 (19)	C10—C17—C19—O2	4.9 (3)
N1—N2—C9—C26	178.13 (15)	C18—C17—C19—N4	0.56 (18)
C7—C8—C9—N2	1.11 (19)	C10—C17—C19—N4	−177.10 (17)
C10—C8—C9—N2	172.25 (15)	C19—N4—C20—C21	−39.9 (3)
C7—C8—C9—C26	−175.66 (17)	N3—N4—C20—C21	138.11 (17)
C10—C8—C9—C26	−4.5 (3)	C19—N4—C20—C25	141.73 (18)
C9—C8—C10—C17	139.90 (16)	N3—N4—C20—C25	−40.3 (2)
C7—C8—C10—C17	−50.9 (2)	C25—C20—C21—C22	−0.2 (3)
C9—C8—C10—C11	−90.77 (19)	N4—C20—C21—C22	−178.54 (17)
C7—C8—C10—C11	78.4 (2)	C20—C21—C22—C23	0.3 (3)
C17—C10—C11—C16	−126.08 (16)	C21—C22—C23—C24	0.0 (3)
C8—C10—C11—C16	100.84 (17)	C22—C23—C24—C25	−0.5 (3)
C17—C10—C11—C12	56.1 (2)	C23—C24—C25—C20	0.6 (3)
C8—C10—C11—C12	−77.01 (19)	C21—C20—C25—C24	−0.3 (3)
C16—C11—C12—C13	0.1 (2)	N4—C20—C25—C24	178.12 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.83 (1)	1.67 (1)	2.5025 (17)	176 (3)
N2—H1N2···N3ⁱ	0.86 (1)	1.90 (1)	2.7544 (19)	174 (2)
C13—H13A···O2ⁱⁱ	0.95	2.58	3.375 (2)	142
C4—H4A···Cg1ⁱⁱⁱ	0.95	2.67	3.5088 (18)	147
C24—H24A···Cg1^iv	0.95	2.86	3.745 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₃ClN₄O₂
M_r	470.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.8809 (2), 11.2046 (2), 18.9376 (3)
β (°)	97.994 (1)
V (Å³)	2286.36 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.41 × 0.13 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.923, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	26858, 6751, 4614
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.121, 1.02
No. of reflections	6751
No. of parameters	317
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.83 (1)	1.67 (1)	2.5025 (17)	176 (3)
N2—H1N2···N3ⁱ	0.86 (1)	1.90 (1)	2.7544 (19)	174 (2)
C13—H13A···O2ⁱⁱ	0.95	2.58	3.375 (2)	142
C4—H4A···Cg1ⁱⁱⁱ	0.95	2.67	3.5088 (18)	147
C24—H24A···Cg1^iv	0.95	2.86	3.745 (2)	155

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641114, India.

Acknowledgements

H-KF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a post–doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burger, J. C. & Iorio, L. C. (1979). Annu. Rep. Med. Chem. 14, 27–35. Google Scholar
Holla, B. S., Kalluraya, B., Sridhar, K., Erick Parke, T. L. & Bhandary, K. K. (1994). Eur. J. Med. Chem. 29, 301–308. CrossRef CAS Web of Science Google Scholar
Kalluraya, B. & Chimbalkar, R. M. (2001). Indian J. Heterocycl. Chem. 11, 171–174. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Windholz, M. (1976). The Merck Index, 9th ed. Boca Raton: Merck & Co. Inc. Google Scholar
Wolff, M. E. (1980). Burgers Medicinal Chemistry, 4th ed. New York: Wiley. Google Scholar

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Volume 64| Part 12| December 2008| Pages o2301-o2302

doi:10.1107/S1600536808036088

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

4-[(4-Chloro­phen­yl)(5-hydr­­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

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Crystal data

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Supporting information

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organic compounds

4-[(4-Chlorophenyl)(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one