3,5-Bis[1-acetyl-5-(4-chloro­phen­yl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethyl­pyridine

Qian, Q.; Zhang, J.; Zhang, M.; He, X.; Xia, Y.-B.

doi:10.1107/S1600536808023921

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1700

doi:10.1107/S1600536808023921

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3,5-Bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethylpyridine

Qun Qian,^a Jun Zhang,^a Min Zhang,^a ^* Xiang He ^a and Yi-Ben Xia ^b

^aDepartment of Chemistry, College of Science, Shanghai University, Shanghai 200444, People's Republic of China, and ^bSchool of Materials Science and Engineering, Shanghai University, Shanghai 200072, People's Republic of China
^*Correspondence e-mail: minzhang1@yeah.net

(Received 25 July 2008; accepted 28 July 2008; online 6 August 2008)

The title compound, C₂₉H₂₇Cl₂N₅O₂, contains a central pyridine ring and two functionalized pyrazoline rings. The pyridine ring and the two attached pyrazoline rings are nearly coplanar, whereas the terminal chlorophenyl rings are nearly perpendicular to the attached pyrazoline rings [dihedral angles = 86.78 (1) and 77.70 (1)°]. Molecules are linked by weak intermolecular C—H⋯O hydrogen bonding.

Related literature

For general background, see: Ahn et al. (2004 ); Palaska et al. (1996 ); Yar et al. (2006 )

Experimental

Crystal data

C₂₉H₂₇Cl₂N₅O₂
M_r = 548.46
Monoclinic, P 2₁
a = 12.345 (3) Å
b = 9.6763 (19) Å
c = 13.268 (3) Å
β = 115.00 (3)°
V = 1436.4 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.926, T_max = 0.950
7509 measured reflections
3736 independent reflections
2520 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.077
S = 0.91
3736 reflections
344 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), 1031 Friedel pairs
Flack parameter: 0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2ⁱ	0.99	2.59	3.358 (3)	135
C17—H17A⋯O2ⁱⁱ	0.95	2.50	3.359 (4)	151
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x, y, z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023921/xu2444sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023921/xu2444Isup2.hkl

checkCIF report

Comment top

The pyrazoline derivatives are well known nitrogen-containing heterocyclic compounds which show various biological activities and pharmacological properties (Palaska et al., 1996). Some of them can be anti-bacterial and anti-fungal, others are anti-diabetic, anti-inflammatory and also active against many Mycobacterias (Ahn et al., 2004; Yar et al., 2006). As the stereochemistry may be an important modulator of biological activity, the crystal structure of the title compound has been determined.

The molecular structure is shown in Fig. 1. There are two chlorophenyl rings bonded with two pyrazoline rings in cis-arrangement, and these two pyrazoline rings are further bonded with the same pyridine ring. The central pyridine ring and two attached pyrazoline rings are nearly coplanar with the dihedral angles of 1.32 (2) and 4.88 (2)°, whereas the dihedral angles between each chlorophenyl plane and the attached pyrazoline planes are 86.78 (1) and 77.70 (1)°.

In the crystal structure, there are weak intermolecular C—H···O hydrogen bonding (Table 1 and Fig. 2).

Related literature top

For general background, see: Ahn et al. (2004); Palaska et al. (1996); Yar et al. (2006)

Experimental top

2,6-Dimethyl-3,5-di-[3-(4-chloro-phenyl)-acryloyl-pyridine (1 mmol, 0.436 g) and 85% hydrazine hydrate solution (4 mmol, 0.235 g) were dissolved in 5 ml of acetic acid solution. The solution was refluxed for 8 h, and allowed to cool to room temperature. The reaction mixture was poured into crushed ice, then neutralized with dilute sodium hydroxide solution. The solid separated was filtered off, washed with water, dried and recrystallized from ethyl acetate to give a colorless compound in a yield of of 40%. Single crystals suitable for X-ray analysis were obtained form tetrahydrofuran at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing diagram of compound (I), Hydrogen bonding is indicated by dashed lines.

3,5-Bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]- 2,6-dimethylpyridine top

Crystal data top

C₂₉H₂₇Cl₂N₅O₂	F(000) = 572
M_r = 548.46	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁	Melting point = 547–549 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 12.345 (3) Å	Cell parameters from 2029 reflections
b = 9.6763 (19) Å	θ = 2.7–20.6°
c = 13.268 (3) Å	µ = 0.26 mm⁻¹
β = 115.00 (3)°	T = 296 K
V = 1436.4 (5) Å³	Block, colorless
Z = 2	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3736 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.926, T_max = 0.950	k = −5→11
7509 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0287P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3736 reflections	Δρ_max = 0.14 e Å⁻³
344 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1031 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (6)

Crystal data top

C₂₉H₂₇Cl₂N₅O₂	V = 1436.4 (5) Å³
M_r = 548.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 12.345 (3) Å	µ = 0.26 mm⁻¹
b = 9.6763 (19) Å	T = 296 K
c = 13.268 (3) Å	0.30 × 0.20 × 0.20 mm
β = 115.00 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3736 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2520 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.950	R_int = 0.027
7509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.077	Δρ_max = 0.14 e Å⁻³
S = 0.91	Δρ_min = −0.15 e Å⁻³
3736 reflections	Absolute structure: Flack (1983), 1031 Friedel pairs
344 parameters	Absolute structure parameter: 0.06 (6)
1 restraint

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
Cl1	0.82566 (10)	0.19017 (14)	0.84787 (9)	0.1067 (4)
Cl2	0.93108 (9)	−0.23669 (14)	0.26803 (10)	0.1163 (4)
N4	0.3040 (2)	0.0470 (3)	−0.03488 (19)	0.0535 (7)
O2	0.4646 (2)	0.0216 (3)	−0.19685 (16)	0.0699 (7)
N2	0.2426 (2)	0.4329 (3)	0.4064 (2)	0.0591 (7)
C3	0.3001 (3)	0.2513 (3)	0.1935 (2)	0.0518 (8)
H3A	0.3772	0.2901	0.2141	0.062*
C2	0.2559 (3)	0.1586 (3)	0.1053 (2)	0.0472 (8)
N5	0.3995 (2)	0.0474 (3)	−0.06575 (19)	0.0520 (7)
N1	0.0772 (2)	0.1372 (3)	0.1322 (2)	0.0595 (7)
C8	0.2922 (3)	0.3870 (3)	0.3447 (2)	0.0511 (8)
N3	0.3251 (2)	0.5240 (3)	0.4848 (2)	0.0588 (7)
C21	0.5046 (3)	0.1276 (3)	0.0106 (2)	0.0498 (8)
H21A	0.5260	0.1990	−0.0324	0.060*
C1	0.1420 (3)	0.1018 (3)	0.0771 (2)	0.0533 (8)
C4	0.2348 (3)	0.2885 (3)	0.2519 (2)	0.0501 (8)
C19	0.3333 (3)	0.1291 (3)	0.0493 (2)	0.0474 (8)
C20	0.4534 (2)	0.1978 (3)	0.0844 (2)	0.0503 (8)
H20A	0.5048	0.1814	0.1641	0.060*
H20B	0.4447	0.2986	0.0705	0.060*
C13	0.5391 (3)	0.4494 (3)	0.5838 (3)	0.0547 (8)
C24	0.6109 (2)	0.0369 (3)	0.0729 (2)	0.0475 (8)
O1	0.3715 (2)	0.6813 (3)	0.6201 (2)	0.0844 (8)
C7	0.0821 (3)	−0.0002 (4)	−0.0160 (3)	0.0701 (10)
H7A	0.0072	−0.0321	−0.0150	0.105*
H7B	0.1351	−0.0793	−0.0061	0.105*
H7C	0.0650	0.0446	−0.0874	0.105*
C29	0.6086 (3)	−0.0608 (4)	0.1481 (3)	0.0580 (9)
H29A	0.5379	−0.0706	0.1593	0.070*
C11	0.2948 (4)	0.6055 (4)	0.5529 (3)	0.0677 (10)
C9	0.4157 (3)	0.4450 (3)	0.3751 (2)	0.0564 (9)
H9A	0.4160	0.5088	0.3169	0.068*
H9B	0.4743	0.3702	0.3860	0.068*
C18	0.5107 (3)	0.3598 (4)	0.6500 (3)	0.0598 (9)
H18A	0.4298	0.3507	0.6388	0.072*
C10	0.4435 (3)	0.5226 (4)	0.4848 (2)	0.0578 (9)
H10A	0.4694	0.6193	0.4797	0.069*
C25	0.7154 (3)	0.0477 (4)	0.0600 (3)	0.0642 (10)
H25A	0.7208	0.1143	0.0097	0.077*
C17	0.5992 (3)	0.2823 (4)	0.7333 (3)	0.0667 (9)
H17A	0.5787	0.2220	0.7790	0.080*
C22	0.3836 (3)	0.0014 (3)	−0.1681 (3)	0.0563 (9)
C28	0.7057 (3)	−0.1451 (4)	0.2079 (3)	0.0667 (10)
H28A	0.7016	−0.2112	0.2591	0.080*
C14	0.6579 (3)	0.4611 (4)	0.6040 (3)	0.0742 (11)
H14A	0.6801	0.5241	0.5611	0.089*
C27	0.8074 (3)	−0.1310 (4)	0.1916 (3)	0.0684 (10)
C6	0.0396 (3)	0.2566 (5)	0.2730 (3)	0.0917 (14)
H6A	−0.0334	0.2013	0.2372	0.138*
H6B	0.0187	0.3549	0.2660	0.138*
H6C	0.0800	0.2318	0.3519	0.138*
C5	0.1217 (3)	0.2283 (3)	0.2175 (3)	0.0572 (9)
C16	0.7161 (3)	0.2940 (4)	0.7486 (3)	0.0690 (10)
C26	0.8133 (3)	−0.0363 (5)	0.1185 (3)	0.0753 (11)
H26A	0.8842	−0.0276	0.1074	0.090*
C15	0.7466 (3)	0.3822 (5)	0.6863 (3)	0.0814 (12)
H15A	0.8277	0.3908	0.6980	0.098*
C12	0.1685 (3)	0.5944 (5)	0.5398 (3)	0.0878 (12)
H12A	0.1567	0.6570	0.5924	0.132*
H12B	0.1525	0.4992	0.5548	0.132*
H12C	0.1136	0.6197	0.4637	0.132*
C23	0.2705 (3)	−0.0739 (4)	−0.2390 (3)	0.0778 (11)
H23A	0.2731	−0.1018	−0.3089	0.117*
H23B	0.2019	−0.0129	−0.2548	0.117*
H23C	0.2629	−0.1561	−0.1994	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0941 (8)	0.1130 (9)	0.1006 (8)	0.0245 (7)	0.0290 (6)	0.0137 (7)
Cl2	0.0693 (7)	0.1272 (11)	0.1354 (10)	0.0249 (7)	0.0267 (6)	0.0115 (8)
N4	0.0520 (16)	0.065 (2)	0.0518 (16)	−0.0009 (14)	0.0295 (13)	−0.0093 (15)
O2	0.0865 (17)	0.0762 (18)	0.0682 (15)	−0.0036 (13)	0.0531 (14)	−0.0109 (13)
N2	0.0685 (18)	0.064 (2)	0.0524 (16)	0.0096 (16)	0.0333 (15)	−0.0045 (15)
C3	0.0518 (18)	0.058 (2)	0.0517 (18)	−0.0006 (17)	0.0278 (16)	−0.0058 (17)
C2	0.0498 (18)	0.051 (2)	0.0464 (18)	0.0020 (15)	0.0262 (16)	−0.0037 (16)
N5	0.0536 (16)	0.0614 (19)	0.0479 (15)	−0.0026 (14)	0.0282 (13)	−0.0081 (14)
N1	0.0504 (16)	0.070 (2)	0.0659 (18)	−0.0028 (14)	0.0323 (15)	−0.0081 (16)
C8	0.063 (2)	0.051 (2)	0.0437 (18)	0.0075 (17)	0.0274 (17)	−0.0005 (16)
N3	0.0655 (18)	0.062 (2)	0.0556 (16)	0.0036 (15)	0.0319 (15)	−0.0152 (15)
C21	0.0572 (19)	0.050 (2)	0.0508 (18)	−0.0131 (17)	0.0315 (16)	−0.0076 (17)
C1	0.0519 (19)	0.059 (2)	0.0488 (19)	−0.0016 (17)	0.0213 (16)	−0.0033 (17)
C4	0.060 (2)	0.050 (2)	0.0499 (19)	0.0034 (17)	0.0320 (16)	0.0011 (17)
C19	0.0526 (19)	0.047 (2)	0.0435 (18)	0.0018 (16)	0.0214 (15)	−0.0054 (16)
C20	0.0570 (19)	0.051 (2)	0.0503 (18)	−0.0052 (16)	0.0297 (16)	−0.0076 (17)
C13	0.067 (2)	0.051 (2)	0.054 (2)	−0.0064 (18)	0.0341 (18)	−0.0127 (17)
C24	0.0502 (19)	0.049 (2)	0.0514 (19)	−0.0069 (17)	0.0292 (16)	−0.0083 (17)
O1	0.109 (2)	0.0778 (19)	0.0720 (17)	0.0029 (17)	0.0441 (16)	−0.0235 (16)
C7	0.065 (2)	0.077 (3)	0.076 (2)	−0.013 (2)	0.037 (2)	−0.018 (2)
C29	0.052 (2)	0.063 (2)	0.067 (2)	−0.0037 (18)	0.0330 (18)	−0.006 (2)
C11	0.084 (3)	0.066 (3)	0.057 (2)	0.021 (2)	0.034 (2)	−0.002 (2)
C9	0.075 (2)	0.052 (2)	0.052 (2)	−0.0078 (18)	0.0363 (18)	−0.0114 (17)
C18	0.064 (2)	0.066 (3)	0.061 (2)	−0.0023 (19)	0.0382 (19)	−0.0068 (19)
C10	0.071 (2)	0.055 (2)	0.056 (2)	−0.0092 (19)	0.0355 (19)	−0.0090 (18)
C25	0.066 (2)	0.070 (3)	0.072 (2)	−0.008 (2)	0.043 (2)	−0.001 (2)
C17	0.085 (3)	0.066 (3)	0.066 (2)	0.004 (2)	0.047 (2)	0.001 (2)
C22	0.067 (2)	0.054 (2)	0.052 (2)	0.0047 (18)	0.0293 (19)	−0.0077 (17)
C28	0.070 (2)	0.069 (3)	0.071 (2)	−0.002 (2)	0.039 (2)	0.002 (2)
C14	0.079 (3)	0.078 (3)	0.080 (3)	−0.020 (2)	0.047 (2)	−0.001 (2)
C27	0.051 (2)	0.076 (3)	0.073 (2)	0.003 (2)	0.0206 (19)	−0.009 (2)
C6	0.075 (2)	0.126 (4)	0.101 (3)	−0.013 (3)	0.063 (2)	−0.034 (3)
C5	0.053 (2)	0.068 (3)	0.059 (2)	0.0039 (18)	0.0314 (17)	−0.0082 (19)
C16	0.069 (2)	0.072 (3)	0.062 (2)	0.003 (2)	0.025 (2)	−0.006 (2)
C26	0.054 (2)	0.092 (3)	0.092 (3)	−0.007 (2)	0.042 (2)	−0.010 (2)
C15	0.064 (3)	0.090 (3)	0.095 (3)	−0.007 (2)	0.039 (2)	0.005 (3)
C12	0.087 (3)	0.101 (3)	0.082 (3)	0.027 (2)	0.042 (2)	−0.015 (2)
C23	0.076 (2)	0.088 (3)	0.069 (2)	−0.005 (2)	0.030 (2)	−0.032 (2)

Geometric parameters (Å, º) top

Cl1—C16	1.752 (4)	C7—H7B	0.9800
Cl2—C27	1.760 (4)	C7—H7C	0.9800
N4—C19	1.291 (3)	C29—C28	1.389 (4)
N4—N5	1.401 (3)	C29—H29A	0.9500
O2—C22	1.227 (3)	C11—C12	1.498 (5)
N2—C8	1.291 (3)	C9—C10	1.543 (4)
N2—N3	1.415 (3)	C9—H9A	0.9900
C3—C4	1.382 (4)	C9—H9B	0.9900
C3—C2	1.390 (4)	C18—C17	1.399 (4)
C3—H3A	0.9500	C18—H18A	0.9500
C2—C1	1.406 (4)	C10—H10A	1.0000
C2—C19	1.465 (4)	C25—C26	1.390 (5)
N5—C22	1.362 (4)	C25—H25A	0.9500
N5—C21	1.484 (3)	C17—C16	1.374 (4)
N1—C1	1.336 (3)	C17—H17A	0.9500
N1—C5	1.355 (4)	C22—C23	1.502 (4)
C8—C4	1.480 (4)	C28—C27	1.367 (4)
C8—C9	1.511 (4)	C28—H28A	0.9500
N3—C11	1.365 (4)	C14—C15	1.400 (5)
N3—C10	1.460 (4)	C14—H14A	0.9500
C21—C24	1.502 (4)	C27—C26	1.359 (5)
C21—C20	1.530 (4)	C6—C5	1.509 (4)
C21—H21A	1.0000	C6—H6A	0.9800
C1—C7	1.508 (4)	C6—H6B	0.9800
C4—C5	1.399 (4)	C6—H6C	0.9800
C19—C20	1.508 (4)	C16—C15	1.348 (5)
C20—H20A	0.9900	C26—H26A	0.9500
C20—H20B	0.9900	C15—H15A	0.9500
C13—C18	1.381 (4)	C12—H12A	0.9800
C13—C14	1.380 (4)	C12—H12B	0.9800
C13—C10	1.519 (4)	C12—H12C	0.9800
C24—C25	1.376 (4)	C23—H23A	0.9800
C24—C29	1.384 (4)	C23—H23B	0.9800
O1—C11	1.231 (4)	C23—H23C	0.9800
C7—H7A	0.9800

C19—N4—N5	106.8 (2)	C8—C9—H9B	111.1
C8—N2—N3	107.0 (3)	C10—C9—H9B	111.1
C4—C3—C2	121.8 (3)	H9A—C9—H9B	109.1
C4—C3—H3A	119.1	C13—C18—C17	121.0 (3)
C2—C3—H3A	119.1	C13—C18—H18A	119.5
C3—C2—C1	117.9 (2)	C17—C18—H18A	119.5
C3—C2—C19	116.4 (3)	N3—C10—C13	114.6 (3)
C1—C2—C19	125.6 (3)	N3—C10—C9	100.4 (2)
C22—N5—N4	120.4 (3)	C13—C10—C9	111.7 (3)
C22—N5—C21	124.5 (3)	N3—C10—H10A	109.9
N4—N5—C21	113.8 (2)	C13—C10—H10A	109.9
C1—N1—C5	119.9 (3)	C9—C10—H10A	109.9
N2—C8—C4	124.1 (3)	C24—C25—C26	121.8 (3)
N2—C8—C9	113.5 (3)	C24—C25—H25A	119.1
C4—C8—C9	122.4 (3)	C26—C25—H25A	119.1
C11—N3—N2	122.1 (3)	C16—C17—C18	119.6 (3)
C11—N3—C10	124.0 (3)	C16—C17—H17A	120.2
N2—N3—C10	113.8 (2)	C18—C17—H17A	120.2
N5—C21—C24	112.2 (2)	O2—C22—N5	117.7 (3)
N5—C21—C20	101.0 (2)	O2—C22—C23	123.1 (3)
C24—C21—C20	114.1 (2)	N5—C22—C23	119.1 (3)
N5—C21—H21A	109.7	C27—C28—C29	118.7 (3)
C24—C21—H21A	109.7	C27—C28—H28A	120.7
C20—C21—H21A	109.7	C29—C28—H28A	120.7
N1—C1—C2	121.2 (3)	C13—C14—C15	121.6 (3)
N1—C1—C7	114.6 (3)	C13—C14—H14A	119.2
C2—C1—C7	124.2 (3)	C15—C14—H14A	119.2
C3—C4—C5	116.5 (3)	C26—C27—C28	120.7 (3)
C3—C4—C8	116.6 (3)	C26—C27—Cl2	120.5 (3)
C5—C4—C8	126.9 (3)	C28—C27—Cl2	118.8 (3)
N4—C19—C2	123.7 (3)	C5—C6—H6A	109.5
N4—C19—C20	114.7 (2)	C5—C6—H6B	109.5
C2—C19—C20	121.6 (3)	H6A—C6—H6B	109.5
C19—C20—C21	103.0 (2)	C5—C6—H6C	109.5
C19—C20—H20A	111.2	H6A—C6—H6C	109.5
C21—C20—H20A	111.2	H6B—C6—H6C	109.5
C19—C20—H20B	111.2	N1—C5—C4	122.7 (3)
C21—C20—H20B	111.2	N1—C5—C6	114.0 (3)
H20A—C20—H20B	109.1	C4—C5—C6	123.3 (3)
C18—C13—C14	117.5 (3)	C15—C16—C17	120.6 (3)
C18—C13—C10	121.9 (3)	C15—C16—Cl1	119.8 (3)
C14—C13—C10	120.3 (3)	C17—C16—Cl1	119.5 (3)
C25—C24—C29	116.6 (3)	C27—C26—C25	119.8 (3)
C25—C24—C21	122.3 (3)	C27—C26—H26A	120.1
C29—C24—C21	121.1 (3)	C25—C26—H26A	120.1
C1—C7—H7A	109.5	C16—C15—C14	119.6 (3)
C1—C7—H7B	109.5	C16—C15—H15A	120.2
H7A—C7—H7B	109.5	C14—C15—H15A	120.2
C1—C7—H7C	109.5	C11—C12—H12A	109.5
H7A—C7—H7C	109.5	C11—C12—H12B	109.5
H7B—C7—H7C	109.5	H12A—C12—H12B	109.5
C28—C29—C24	122.5 (3)	C11—C12—H12C	109.5
C28—C29—H29A	118.7	H12A—C12—H12C	109.5
C24—C29—H29A	118.7	H12B—C12—H12C	109.5
O1—C11—N3	118.8 (3)	C22—C23—H23A	109.5
O1—C11—C12	124.8 (3)	C22—C23—H23B	109.5
N3—C11—C12	116.4 (3)	H23A—C23—H23B	109.5
C8—C9—C10	103.2 (2)	C22—C23—H23C	109.5
C8—C9—H9A	111.1	H23A—C23—H23C	109.5
C10—C9—H9A	111.1	H23B—C23—H23C	109.5

C4—C3—C2—C1	−0.5 (5)	N2—N3—C11—C12	−0.4 (5)
C4—C3—C2—C19	179.3 (3)	C10—N3—C11—C12	179.1 (3)
C19—N4—N5—C22	−162.3 (3)	N2—C8—C9—C10	8.9 (3)
C19—N4—N5—C21	5.3 (3)	C4—C8—C9—C10	−171.8 (3)
N3—N2—C8—C4	−179.9 (3)	C14—C13—C18—C17	−1.0 (5)
N3—N2—C8—C9	−0.6 (3)	C10—C13—C18—C17	173.1 (3)
C8—N2—N3—C11	170.7 (3)	C11—N3—C10—C13	74.2 (4)
C8—N2—N3—C10	−8.9 (3)	N2—N3—C10—C13	−106.2 (3)
C22—N5—C21—C24	−79.9 (4)	C11—N3—C10—C9	−165.9 (3)
N4—N5—C21—C24	113.0 (3)	N2—N3—C10—C9	13.7 (3)
C22—N5—C21—C20	158.2 (3)	C18—C13—C10—N3	17.2 (4)
N4—N5—C21—C20	−8.9 (3)	C14—C13—C10—N3	−168.8 (3)
C5—N1—C1—C2	−0.6 (5)	C18—C13—C10—C9	−96.1 (3)
C5—N1—C1—C7	−179.9 (3)	C14—C13—C10—C9	77.8 (4)
C3—C2—C1—N1	1.0 (4)	C8—C9—C10—N3	−12.5 (3)
C19—C2—C1—N1	−178.8 (3)	C8—C9—C10—C13	109.4 (3)
C3—C2—C1—C7	−179.9 (3)	C29—C24—C25—C26	0.7 (5)
C19—C2—C1—C7	0.4 (5)	C21—C24—C25—C26	179.7 (3)
C2—C3—C4—C5	−0.2 (5)	C13—C18—C17—C16	−0.9 (5)
C2—C3—C4—C8	179.4 (3)	N4—N5—C22—O2	170.1 (3)
N2—C8—C4—C3	179.2 (3)	C21—N5—C22—O2	3.8 (5)
C9—C8—C4—C3	0.0 (4)	N4—N5—C22—C23	−11.4 (4)
N2—C8—C4—C5	−1.2 (5)	C21—N5—C22—C23	−177.6 (3)
C9—C8—C4—C5	179.6 (3)	C24—C29—C28—C27	−0.1 (5)
N5—N4—C19—C2	179.1 (3)	C18—C13—C14—C15	1.9 (5)
N5—N4—C19—C20	1.1 (3)	C10—C13—C14—C15	−172.3 (3)
C3—C2—C19—N4	−178.9 (3)	C29—C28—C27—C26	0.1 (5)
C1—C2—C19—N4	0.9 (5)	C29—C28—C27—Cl2	179.5 (3)
C3—C2—C19—C20	−1.1 (4)	C1—N1—C5—C4	−0.2 (5)
C1—C2—C19—C20	178.7 (3)	C1—N1—C5—C6	−179.0 (3)
N4—C19—C20—C21	−6.5 (3)	C3—C4—C5—N1	0.6 (5)
C2—C19—C20—C21	175.5 (3)	C8—C4—C5—N1	−179.0 (3)
N5—C21—C20—C19	8.4 (3)	C3—C4—C5—C6	179.3 (3)
C24—C21—C20—C19	−112.2 (3)	C8—C4—C5—C6	−0.3 (5)
N5—C21—C24—C25	116.5 (3)	C18—C17—C16—C15	1.9 (5)
C20—C21—C24—C25	−129.5 (3)	C18—C17—C16—Cl1	−176.6 (3)
N5—C21—C24—C29	−64.7 (4)	C28—C27—C26—C25	0.3 (6)
C20—C21—C24—C29	49.4 (4)	Cl2—C27—C26—C25	−179.1 (3)
C25—C24—C29—C28	−0.3 (5)	C24—C25—C26—C27	−0.8 (5)
C21—C24—C29—C28	−179.3 (3)	C17—C16—C15—C14	−1.0 (6)
N2—N3—C11—O1	179.2 (3)	Cl1—C16—C15—C14	177.5 (3)
C10—N3—C11—O1	−1.3 (5)	C13—C14—C15—C16	−1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱ	0.99	2.59	3.358 (3)	135
C17—H17A···O2ⁱⁱ	0.95	2.50	3.359 (4)	151

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₇Cl₂N₅O₂
M_r	548.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	12.345 (3), 9.6763 (19), 13.268 (3)
β (°)	115.00 (3)
V (Å³)	1436.4 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.926, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	7509, 3736, 2520
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.077, 0.91
No. of reflections	3736
No. of parameters	344
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15
Absolute structure	Flack (1983), 1031 Friedel pairs
Absolute structure parameter	0.06 (6)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱ	0.99	2.59	3.358 (3)	135
C17—H17A···O2ⁱⁱ	0.95	2.50	3.359 (4)	151

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

Acknowledgements

The authors thank the Instrument Analysis and Research Center of Shanghai University for the data collection. The project was supported by the Key Subject of Shanghai Municipal Education Commission (grant No. J50102) and the Foundation of the Education Commission of Shanghai Municipality, China (grant No. 08zz44).

References

Ahn, J. H., Kim, H. M., Jung, S. H., Kang, S. K., Kim, K. R., Rhee, S. D., Yang, S. D., Cheon, H. G. & Kim, S. S. (2004). Bioorg. Med. Chem. Lett. 14, 4461–4465. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Palaska, E., Erol, D. & Demirdamar, R. (1996). Eur. J. Med. Chem. 31, 43–47. CrossRef CAS Web of Science 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
Yar, M. S., Siddiqui, A. A. & Ali, M. A. (2006). Bioorg. Med. Chem. Lett. 16, 4571–4574. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 9| September 2008| Page o1700

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

3,5-Bis[1-acetyl-5-(4-chloro­phen­yl)-4,5-di­hydro-1H-pyrazol-3-yl]-2,6-di­methyl­pyridine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

3,5-Bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethylpyridine