[3-(4-Chloro­phen­yl)-5-hydr­oxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3-pyrid­yl)methanone

Fun, H.-K.; Jebas, S.R.; Rao, J.N.; Kalluraya, B.

doi:10.1107/S1600536808037161

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages o2363-o2364

doi:10.1107/S1600536808037161

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[3-(4-Chlorophenyl)-5-hydroxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3-pyridyl)methanone

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Jyothi N. Rao ^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 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 November 2008; accepted 10 November 2008; online 13 November 2008)

In the title compound, C₂₁H₁₆ClN₃O₂, the dihedral angles formed by the pyrazole ring with the pyridyl, phenylene and phenyl rings are 6.80 (5), 9.23 (5) and 74.96 (5)°, respectively. The phenyl and phenylene rings are inclined at 80.14 (2)°. Intramolecular O—H⋯O and C—H⋯N hydrogen bonds generate S(6) ring motifs. The crystal packing is strengthened by short intermolecular O—H⋯N, C—H⋯O hydrogen bonds and π–π stacking interactions with centroid–centroid distances of 3.6247 (5)–3.7205 (5) Å, together with intermolecular short O⋯N contacts [2.7682 (11) Å]. Molecules are linked into infinite chains along [100].

Related literature

For the biological applications of pyrazoles, see: Kalluraya & Ramesh (2001 ); Watanabe et al. (1998 ); Yuhong & Rajender (2005 ). For bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₁₆ClN₃O₂
M_r = 377.82
Triclinic, $[P \overline 1]$
a = 7.5916 (1) Å
b = 9.7644 (1) Å
c = 12.5474 (2) Å
α = 104.424 (1)°
β = 94.960 (1)°
γ = 96.081 (1)°
V = 889.55 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100.0 (1) K
0.47 × 0.29 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.896, T_max = 0.957
20326 measured reflections
6385 independent reflections
5630 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.04
6385 reflections
248 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.824 (13)	2.340 (14)	2.8463 (9)	120.3 (13)
O2—H1O2⋯N3ⁱ	0.824 (13)	2.027 (14)	2.7682 (11)	149.5 (14)
C8—H8A⋯O2ⁱⁱ	0.97	2.55	3.4836 (11)	163
C13—H13A⋯O1ⁱⁱⁱ	0.93	2.46	3.3294 (12)	156
C21—H21A⋯N1	0.93	2.21	2.8600 (12)	127
C14—H14A⋯Cg2^iv	0.93	2.90	3.6968 (11)	144
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+2; (iii) -x+1, -y, -z+1; (iv) -x, -y, -z+1. Cg2 is the centroid of the N3/C17–C21 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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/S1600536808037161/ng2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037161/ng2515Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds occur very widely in nature and are essential to life. Nitrogen-containing heterocyclic molecules constitute the largest portion of chemical entities, which are part of many natural products, fine chemicals, and biologically active pharmaceuticals vital for enhancing the quality of life. 4,5-Dihydro-pyrazoles, pyrazolidines and 1,2-dihydro-phthalazines are important classes of heterocycles useful as pesticides, anticonvulsants, and potent vasorelaxing agents (Kalluraya et al., 2001; Watanabe et al., 1998; Yuhong & Rajender, 2005). The pyrazoline function is quite stable and has inspired chemists to utilize this stable fragment in bioactive moieties to synthesize new compounds. Prompted by these review, we have synthesized this new substituted pyrazoline derivative and report its crystal structure.

Bond lengths and angles in (I) (Fig. 1) are found to have normal values (Allen et al., 1987). The dihedral angle formed by the pyrazole (N1/N2/C7—C9) ring with the pyridine ring (N3/C17—C21) and the two benzene rings (C1—C6; C10—C15) are 6.80 (5), 9.23 (5) and 74.96 (5)° respectively. The benzene rings (C1—C6; C10—C15) form dihedral angle of 80.14 (2)°, indicating that they are inclined to each other. Intramolecular C—H···N and O—H···O hydrogen bonds generate S(6) ring motifs. (Bernstein et al., 1995).

The crystal packing is consolidated by intermolecular O—H···N and C—H···O hydrogen bonding (Table 1). Furthermore, the packing is strengthened by π—π stacking interactions involving the pyrazole (N1—N2/C7—C9) (Cg1) ring and the symmetry related benzene (C10—C15) (Cg4) ring [Cg1···Cg4^v=3.7787 (6) Å; symmetry code: (v) X,Y,Z]; pyridine (N3/C17—C21) (Cg2) ring and the symmetry related benzene (C1—C6) (Cg3) ring [Cg2···Cg3^vi=3.6247 (5) Å; symmetry code: (vi) –X,-Y,2-Z] and between symmetry related benzene (C1—C6) (Cg3) rings [Cg3···Cg3^vii = 3.7205 (5) Å; symmetry code: (vii) –X,1-Y,2-Z] together with intermolecular O···N = 2.7682 (11)Å short contacts. In the crystal packing, the molecules are linked into infinite one dimensional chains along the [100] direction (Fig 2).

Related literature top

For the biological applications of pyrazoles, see: Kalluraya et al. (2001); Watanabe et al. (1998); Yuhong & Rajender (2005). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). Cg2 is the centroid of the N3/C17–C21ring.

Experimental top

A mixture of 1-phenyl-3-(4-chloro phenyl)-2,3-di-bromo propan-1-one (0.01 mol), nicotinic hydrazide (0.01 mol) and trimethylamine (0.04 mol) in ethanol (30 mL) was refluxed for 8 h. The contents were poured onto crushed ice with stirring. The solid mass separated was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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 down the a axis.

[3-(4-Chlorophenyl)-5-hydroxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3- pyridyl)methanone top

Crystal data top

C₂₁H₁₆ClN₃O₂	Z = 2
M_r = 377.82	F(000) = 392
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5916 (1) Å	Cell parameters from 9943 reflections
b = 9.7644 (1) Å	θ = 3.1–37.5°
c = 12.5474 (2) Å	µ = 0.24 mm⁻¹
α = 104.424 (1)°	T = 100 K
β = 94.960 (1)°	Block, colourless
γ = 96.081 (1)°	0.47 × 0.29 × 0.19 mm
V = 889.55 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6385 independent reflections
Radiation source: fine-focus sealed tube	5630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.896, T_max = 0.957	k = −14→14
20326 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2362P] where P = (F_o² + 2F_c²)/3
6385 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.54 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₁₆ClN₃O₂	γ = 96.081 (1)°
M_r = 377.82	V = 889.55 (2) Å³
Triclinic, P1	Z = 2
a = 7.5916 (1) Å	Mo Kα radiation
b = 9.7644 (1) Å	µ = 0.24 mm⁻¹
c = 12.5474 (2) Å	T = 100 K
α = 104.424 (1)°	0.47 × 0.29 × 0.19 mm
β = 94.960 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6385 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5630 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.957	R_int = 0.023
20326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.54 e Å⁻³
6385 reflections	Δρ_min = −0.26 e Å⁻³
248 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	−0.18759 (3)	0.58111 (2)	1.24148 (2)	0.02272 (7)
O1	0.24543 (9)	−0.22304 (7)	0.66899 (5)	0.01553 (13)
O2	0.47798 (8)	−0.05281 (7)	0.85593 (5)	0.01450 (12)
N1	0.05961 (10)	0.04156 (8)	0.85564 (6)	0.01321 (13)
N2	0.17594 (9)	−0.03622 (8)	0.79391 (6)	0.01266 (13)
N3	−0.36717 (10)	−0.27300 (9)	0.73008 (7)	0.01823 (15)
C1	−0.11452 (12)	0.23011 (9)	1.01516 (7)	0.01448 (15)
H1A	−0.1821	0.1448	0.9752	0.017*
C2	−0.19255 (12)	0.32951 (10)	1.08935 (7)	0.01548 (16)
H2A	−0.3119	0.3113	1.0994	0.019*
C3	−0.08985 (13)	0.45689 (9)	1.14851 (7)	0.01577 (16)
C4	0.08865 (13)	0.48666 (9)	1.13548 (7)	0.01624 (16)
H4A	0.1555	0.5722	1.1756	0.019*
C5	0.16553 (12)	0.38617 (9)	1.06134 (7)	0.01500 (15)
H5A	0.2852	0.4047	1.0523	0.018*
C6	0.06584 (11)	0.25743 (9)	1.00002 (7)	0.01290 (14)
C7	0.15147 (11)	0.15330 (9)	0.92314 (7)	0.01247 (14)
C8	0.34900 (11)	0.16151 (9)	0.91685 (7)	0.01392 (15)
H8A	0.4118	0.1521	0.9848	0.017*
H8B	0.3961	0.2510	0.9030	0.017*
C9	0.36523 (11)	0.03425 (9)	0.81857 (7)	0.01211 (14)
C10	0.42505 (12)	0.08305 (9)	0.71939 (7)	0.01367 (15)
C11	0.60717 (13)	0.11624 (10)	0.71445 (8)	0.01826 (17)
H11A	0.6901	0.1036	0.7690	0.022*
C12	0.66489 (15)	0.16839 (11)	0.62776 (9)	0.0236 (2)
H12A	0.7863	0.1903	0.6248	0.028*
C13	0.54216 (16)	0.18775 (11)	0.54588 (8)	0.0245 (2)
H13A	0.5810	0.2208	0.4874	0.029*
C14	0.36126 (16)	0.15747 (11)	0.55197 (8)	0.0227 (2)
H14A	0.2786	0.1718	0.4979	0.027*
C15	0.30233 (13)	0.10574 (10)	0.63848 (8)	0.01771 (16)
H15A	0.1807	0.0863	0.6422	0.021*
C16	0.12920 (11)	−0.16587 (9)	0.71942 (7)	0.01213 (14)
C17	−0.05871 (11)	−0.24069 (9)	0.69814 (7)	0.01225 (14)
C18	−0.08787 (12)	−0.36918 (10)	0.61570 (8)	0.01686 (16)
H18A	0.0050	−0.4016	0.5768	0.020*
C19	−0.25619 (13)	−0.44831 (10)	0.59202 (8)	0.01974 (18)
H19A	−0.2776	−0.5344	0.5376	0.024*
C20	−0.39171 (12)	−0.39616 (10)	0.65129 (8)	0.01884 (17)
H20A	−0.5044	−0.4492	0.6355	0.023*
C21	−0.20374 (11)	−0.19778 (10)	0.75323 (8)	0.01554 (16)
H21A	−0.1862	−0.1128	0.8088	0.019*
H1O2	0.488 (2)	−0.1208 (13)	0.8037 (10)	0.026 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02952 (12)	0.01698 (11)	0.02199 (12)	0.00842 (8)	0.01020 (9)	0.00106 (8)
O1	0.0147 (3)	0.0150 (3)	0.0160 (3)	0.0030 (2)	0.0043 (2)	0.0011 (2)
O2	0.0147 (3)	0.0148 (3)	0.0141 (3)	0.0036 (2)	0.0005 (2)	0.0036 (2)
N1	0.0140 (3)	0.0118 (3)	0.0129 (3)	0.0026 (2)	0.0031 (2)	0.0008 (2)
N2	0.0110 (3)	0.0120 (3)	0.0133 (3)	0.0011 (2)	0.0025 (2)	0.0000 (2)
N3	0.0120 (3)	0.0183 (4)	0.0217 (4)	0.0009 (3)	−0.0001 (3)	0.0015 (3)
C1	0.0157 (3)	0.0130 (4)	0.0143 (4)	0.0018 (3)	0.0019 (3)	0.0028 (3)
C2	0.0169 (4)	0.0154 (4)	0.0151 (4)	0.0038 (3)	0.0035 (3)	0.0045 (3)
C3	0.0218 (4)	0.0131 (4)	0.0134 (4)	0.0057 (3)	0.0045 (3)	0.0030 (3)
C4	0.0214 (4)	0.0118 (4)	0.0146 (4)	0.0016 (3)	0.0029 (3)	0.0015 (3)
C5	0.0170 (4)	0.0126 (4)	0.0142 (4)	0.0007 (3)	0.0022 (3)	0.0018 (3)
C6	0.0156 (3)	0.0113 (3)	0.0115 (3)	0.0022 (3)	0.0019 (3)	0.0023 (3)
C7	0.0141 (3)	0.0115 (3)	0.0118 (3)	0.0018 (3)	0.0019 (3)	0.0027 (3)
C8	0.0135 (3)	0.0138 (4)	0.0123 (3)	0.0003 (3)	0.0017 (3)	0.0000 (3)
C9	0.0111 (3)	0.0126 (3)	0.0121 (3)	0.0006 (3)	0.0012 (3)	0.0026 (3)
C10	0.0172 (4)	0.0110 (3)	0.0124 (3)	0.0010 (3)	0.0033 (3)	0.0021 (3)
C11	0.0186 (4)	0.0180 (4)	0.0175 (4)	−0.0013 (3)	0.0045 (3)	0.0039 (3)
C12	0.0289 (5)	0.0178 (4)	0.0233 (5)	−0.0033 (4)	0.0120 (4)	0.0035 (3)
C13	0.0433 (6)	0.0135 (4)	0.0177 (4)	−0.0002 (4)	0.0113 (4)	0.0047 (3)
C14	0.0382 (6)	0.0153 (4)	0.0153 (4)	0.0045 (4)	0.0017 (4)	0.0055 (3)
C15	0.0228 (4)	0.0149 (4)	0.0156 (4)	0.0031 (3)	0.0017 (3)	0.0043 (3)
C16	0.0133 (3)	0.0116 (3)	0.0111 (3)	0.0014 (3)	0.0011 (3)	0.0023 (3)
C17	0.0122 (3)	0.0115 (3)	0.0123 (3)	0.0017 (3)	0.0002 (3)	0.0022 (3)
C18	0.0165 (4)	0.0141 (4)	0.0169 (4)	0.0008 (3)	0.0013 (3)	−0.0009 (3)
C19	0.0192 (4)	0.0150 (4)	0.0203 (4)	−0.0015 (3)	−0.0008 (3)	−0.0017 (3)
C20	0.0149 (4)	0.0181 (4)	0.0205 (4)	−0.0017 (3)	−0.0023 (3)	0.0025 (3)
C21	0.0126 (3)	0.0143 (4)	0.0177 (4)	0.0016 (3)	0.0006 (3)	0.0007 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.7373 (9)	C8—H8A	0.9700
O1—C16	1.2311 (10)	C8—H8B	0.9700
O2—C9	1.3994 (11)	C9—C10	1.5262 (12)
O2—H1O2	0.823 (9)	C10—C15	1.3928 (13)
N1—C7	1.2924 (11)	C10—C11	1.3965 (12)
N1—N2	1.3870 (10)	C11—C12	1.3948 (13)
N2—C16	1.3638 (11)	C11—H11A	0.9300
N2—C9	1.4972 (11)	C12—C13	1.3885 (17)
N3—C20	1.3367 (12)	C12—H12A	0.9300
N3—C21	1.3422 (11)	C13—C14	1.3866 (16)
C1—C2	1.3880 (12)	C13—H13A	0.9300
C1—C6	1.4053 (12)	C14—C15	1.3938 (13)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3929 (13)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.5021 (11)
C3—C4	1.3879 (13)	C17—C18	1.3957 (12)
C4—C5	1.3889 (12)	C17—C21	1.3966 (12)
C4—H4A	0.9300	C18—C19	1.3889 (12)
C5—C6	1.4003 (12)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.3876 (14)
C6—C7	1.4652 (12)	C19—H19A	0.9300
C7—C8	1.5032 (12)	C20—H20A	0.9300
C8—C9	1.5412 (12)	C21—H21A	0.9300

C9—O2—H1O2	108.8 (10)	C10—C9—C8	111.83 (7)
C7—N1—N2	108.27 (7)	C15—C10—C11	119.31 (8)
C16—N2—N1	125.12 (7)	C15—C10—C9	121.51 (8)
C16—N2—C9	121.54 (7)	C11—C10—C9	118.99 (8)
N1—N2—C9	113.32 (7)	C12—C11—C10	120.09 (9)
C20—N3—C21	118.29 (8)	C12—C11—H11A	120.0
C2—C1—C6	120.46 (8)	C10—C11—H11A	120.0
C2—C1—H1A	119.8	C13—C12—C11	120.40 (10)
C6—C1—H1A	119.8	C13—C12—H12A	119.8
C1—C2—C3	119.15 (8)	C11—C12—H12A	119.8
C1—C2—H2A	120.4	C14—C13—C12	119.51 (9)
C3—C2—H2A	120.4	C14—C13—H13A	120.2
C4—C3—C2	121.67 (8)	C12—C13—H13A	120.2
C4—C3—Cl1	119.23 (7)	C13—C14—C15	120.49 (10)
C2—C3—Cl1	119.10 (7)	C13—C14—H14A	119.8
C3—C4—C5	118.69 (8)	C15—C14—H14A	119.8
C3—C4—H4A	120.7	C10—C15—C14	120.18 (9)
C5—C4—H4A	120.7	C10—C15—H15A	119.9
C4—C5—C6	121.12 (8)	C14—C15—H15A	119.9
C4—C5—H5A	119.4	O1—C16—N2	118.64 (8)
C6—C5—H5A	119.4	O1—C16—C17	119.41 (8)
C5—C6—C1	118.91 (8)	N2—C16—C17	121.95 (7)
C5—C6—C7	119.70 (8)	C18—C17—C21	117.32 (8)
C1—C6—C7	121.37 (8)	C18—C17—C16	115.35 (7)
N1—C7—C6	121.37 (8)	C21—C17—C16	127.30 (8)
N1—C7—C8	113.88 (7)	C19—C18—C17	119.68 (9)
C6—C7—C8	124.71 (7)	C19—C18—H18A	120.2
C7—C8—C9	103.47 (7)	C17—C18—H18A	120.2
C7—C8—H8A	111.1	C20—C19—C18	118.56 (9)
C9—C8—H8A	111.1	C20—C19—H19A	120.7
C7—C8—H8B	111.1	C18—C19—H19A	120.7
C9—C8—H8B	111.1	N3—C20—C19	122.80 (8)
H8A—C8—H8B	109.0	N3—C20—H20A	118.6
O2—C9—N2	111.30 (7)	C19—C20—H20A	118.6
O2—C9—C10	113.38 (7)	N3—C21—C17	123.34 (8)
N2—C9—C10	110.73 (7)	N3—C21—H21A	118.3
O2—C9—C8	108.31 (7)	C17—C21—H21A	118.3
N2—C9—C8	100.55 (6)

C7—N1—N2—C16	175.28 (8)	N2—C9—C10—C15	21.78 (11)
C7—N1—N2—C9	−3.15 (10)	C8—C9—C10—C15	−89.47 (10)
C6—C1—C2—C3	0.11 (13)	O2—C9—C10—C11	−37.34 (11)
C1—C2—C3—C4	−0.26 (14)	N2—C9—C10—C11	−163.27 (8)
C1—C2—C3—Cl1	−179.91 (7)	C8—C9—C10—C11	85.48 (10)
C2—C3—C4—C5	0.00 (14)	C15—C10—C11—C12	−1.49 (14)
Cl1—C3—C4—C5	179.66 (7)	C9—C10—C11—C12	−176.55 (8)
C3—C4—C5—C6	0.41 (14)	C10—C11—C12—C13	0.03 (15)
C4—C5—C6—C1	−0.56 (13)	C11—C12—C13—C14	1.25 (15)
C4—C5—C6—C7	−179.54 (8)	C12—C13—C14—C15	−1.05 (15)
C2—C1—C6—C5	0.29 (13)	C11—C10—C15—C14	1.69 (14)
C2—C1—C6—C7	179.26 (8)	C9—C10—C15—C14	176.63 (8)
N2—N1—C7—C6	179.99 (7)	C13—C14—C15—C10	−0.43 (14)
N2—N1—C7—C8	−1.91 (10)	N1—N2—C16—O1	179.18 (8)
C5—C6—C7—N1	−171.57 (8)	C9—N2—C16—O1	−2.51 (12)
C1—C6—C7—N1	9.47 (13)	N1—N2—C16—C17	−1.32 (13)
C5—C6—C7—C8	10.55 (13)	C9—N2—C16—C17	176.99 (7)
C1—C6—C7—C8	−168.42 (8)	O1—C16—C17—C18	−3.55 (12)
N1—C7—C8—C9	5.84 (10)	N2—C16—C17—C18	176.95 (8)
C6—C7—C8—C9	−176.14 (8)	O1—C16—C17—C21	174.65 (9)
C16—N2—C9—O2	−57.55 (10)	N2—C16—C17—C21	−4.85 (14)
N1—N2—C9—O2	120.95 (8)	C21—C17—C18—C19	−0.15 (14)
C16—N2—C9—C10	69.54 (10)	C16—C17—C18—C19	178.25 (8)
N1—N2—C9—C10	−111.97 (8)	C17—C18—C19—C20	0.35 (15)
C16—N2—C9—C8	−172.11 (8)	C21—N3—C20—C19	−0.70 (15)
N1—N2—C9—C8	6.39 (9)	C18—C19—C20—N3	0.08 (16)
C7—C8—C9—O2	−123.48 (7)	C20—N3—C21—C17	0.92 (14)
C7—C8—C9—N2	−6.68 (8)	C18—C17—C21—N3	−0.51 (14)
C7—C8—C9—C10	110.87 (8)	C16—C17—C21—N3	−178.68 (9)
O2—C9—C10—C15	147.71 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.82 (1)	2.34 (1)	2.8463 (9)	120 (1)
O2—H1O2···N3ⁱ	0.82 (1)	2.03 (1)	2.7682 (11)	150 (1)
C8—H8A···O2ⁱⁱ	0.97	2.55	3.4836 (11)	163
C13—H13A···O1ⁱⁱⁱ	0.93	2.46	3.3294 (12)	156
C21—H21A···N1	0.93	2.21	2.8600 (12)	127
C14—H14A···Cg2^iv	0.93	2.90	3.6968 (11)	144

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆ClN₃O₂
M_r	377.82
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.5916 (1), 9.7644 (1), 12.5474 (2)
α, β, γ (°)	104.424 (1), 94.960 (1), 96.081 (1)
V (Å³)	889.55 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.47 × 0.29 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.896, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	20326, 6385, 5630
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.04
No. of reflections	6385
No. of parameters	248
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.26

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	0.824 (13)	2.340 (14)	2.8463 (9)	120.3 (13)
O2—H1O2···N3ⁱ	0.824 (13)	2.027 (14)	2.7682 (11)	149.5 (14)
C8—H8A···O2ⁱⁱ	0.97	2.55	3.4836 (11)	163
C13—H13A···O1ⁱⁱⁱ	0.93	2.46	3.3294 (12)	156
C21—H21A···N1	0.93	2.21	2.8600 (12)	127
C14—H14A···Cg2^iv	0.93	2.90	3.6968 (11)	144

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a postdoctoral 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
Kalluraya, B. & Ramesh, M. C. (2001). Indian J. Heterocycl. Chem. 11, 171–172. 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
Watanabe, N., Kabasawa, Y., Takase, Y., Matsukura, M., Miyazaki, K., Ishihara, H., Kodama, K. & Adachi, H. (1998). J. Med. Chem. 41, 3367–3372. Web of Science CrossRef CAS PubMed Google Scholar
Yuhong, J. & Rajender, S. V. (2005). Tetrahedron Lett. 46, 6011–6014. Google Scholar

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Volume 64| Part 12| December 2008| Pages o2363-o2364

doi:10.1107/S1600536808037161

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

[3-(4-Chloro­phen­yl)-5-hydr­­oxy-5-phenyl-4,5-di­hydro-1H-pyrazol-1-yl](3-pyrid­yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

[3-(4-Chlorophenyl)-5-hydroxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3-pyridyl)methanone