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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o865–o866.
Published online 2009 March 25. doi:  10.1107/S1600536809010290
PMCID: PMC2968942

1-[(6-Chloro-3-pyrid­yl)meth­yl]-N-(4-ethoxy­phen­yl)-3-phenyl-1H-pyrazole-5-carboxamide

Abstract

In the title compound, C24H21ClN4O2, the pyrazole ring makes dihedral angles of 7.70 (11), 89.17 (11) and 40.68 (11)° with the phenyl, pyridine and ethoxy­phenyl rings, respectively. There are some intra­molecular C—H(...)O and C—H(...)π bonds giving rigidity to the mol­ecule, while weak inter­molecular N—H(...)N and C—H(...)π hydrogen bonds link the mol­ecules into a two-dimensional structure.

Related literature

For the biological properties of pyrazole derivatives, see: Jia et al. (2004 [triangle]); Wei et al. (2006 [triangle]); Xia et al. (2007 [triangle]). For the synthesis and bioactivity evaluation of pyrazole derivatives, see: Zhang et al. (2008 [triangle]); Zhao et al. (2008 [triangle]); Tang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o865-scheme1.jpg

Experimental

Crystal data

  • C24H21ClN4O2
  • M r = 432.90
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o865-efi1.jpg
  • a = 10.0697 (12) Å
  • b = 5.1399 (6) Å
  • c = 40.990 (5) Å
  • β = 96.446 (2)°
  • V = 2108.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 298 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.96, T max = 0.98
  • 10472 measured reflections
  • 3699 independent reflections
  • 2571 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.104
  • S = 1.03
  • 3699 reflections
  • 280 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010290/bg2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010290/bg2246Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This study was supported by the Science and Technology Developmental Project of Shandong Province (2008 GG10002034).

supplementary crystallographic information

Comment

Pyrazole framework plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), and antitumour (Wei et al., 2006; Xia et al. (2007)) activities. As part of our continuing project of the study on the synthesis and evaluation of pyrazole derivatives (Tang et al., 2007 and Zhao et al.,2008; Zhang et al., 2008), we report here the synthesis and crystal structure of the title compound C24H21ClN4O2. The pyrazole ring makes dihedral angles of 7.70 (11)°, 89.17 (11)° and 40.68 (11)° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H···O and C—H···π bonds giving rigidity to the molecule (first three entries in Table 1), while weak intermolecular N—H···N and C—H···π hydrogen bonds (last two entries in Table 1) link the molecules into a 2D structure.

Experimental

1-(6-Chloropyridin-3-ylmethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid (0.31 g, 1 mmol) and thionyl chloride (0.60 g, 5 mmol) were added to a flask with a condenser and heated to reflux for 4 h. After completion of the reaction (by TLC monitoring), the excess thionyl chloride was evaporated under reduced pressure. To the solution of the crude product, 1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-pyrazole-5-carbonyl chloride (0.332 g, 1 mmol), and triethylamine (0.15 g, 1 mmol) in dichloromethane (20 ml), the solution of 4-ethoxyaniline (0.14 g, 1 mmol) in dichloromethane (20 ml) was added and the mixture was stirred for 20 h at room temperature. Then the mixture was washed with water (20 ml x 3). After dried over anhydrous MgSO4 the mixture was filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using mixture of dichloromethane and ethyl acetate (10/1) as eluent (yield 43%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate/hexane at room temperature for 10 days.

Refinement

All H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, N—H = 0.86Å and with Uiso(H)=1.2Ueq(C, N) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing atom and centroid labels. Displacement ellipsoids drawn at the 50% probability level for non-H atoms.

Crystal data

C24H21ClN4O2F(000) = 904
Mr = 432.90Dx = 1.364 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2064 reflections
a = 10.0697 (12) Åθ = 2.7–22.1°
b = 5.1399 (6) ŵ = 0.21 mm1
c = 40.990 (5) ÅT = 298 K
β = 96.446 (2)°Block, colourless
V = 2108.1 (4) Å30.15 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3699 independent reflections
Radiation source: fine-focus sealed tube2571 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −9→11
Tmin = 0.96, Tmax = 0.98k = −6→6
10472 measured reflectionsl = −46→48

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3478P] where P = (Fo2 + 2Fc2)/3
3699 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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)

xyzUiso*/Ueq
Cl10.71782 (6)−0.22109 (13)0.164051 (17)0.0697 (2)
O10.10720 (14)0.0159 (3)0.08714 (4)0.0596 (4)
O2−0.32793 (14)−0.7133 (3)0.00202 (4)0.0592 (4)
N10.15163 (15)0.5760 (3)0.16155 (4)0.0401 (4)
N20.14531 (15)0.4370 (3)0.13344 (4)0.0382 (4)
N30.60325 (16)0.1539 (4)0.12864 (4)0.0478 (5)
N4−0.10977 (15)−0.0112 (3)0.09696 (4)0.0453 (4)
H4−0.16700.04860.10910.054*
C10.04487 (18)0.5012 (4)0.17605 (5)0.0384 (5)
C2−0.02871 (19)0.3133 (4)0.15696 (5)0.0420 (5)
H2−0.10700.23220.16160.050*
C30.03779 (18)0.2730 (4)0.13003 (5)0.0381 (5)
C40.02032 (19)0.6110 (4)0.20807 (5)0.0395 (5)
C5−0.0794 (2)0.5097 (4)0.22505 (5)0.0509 (6)
H5−0.13040.37040.21620.061*
C6−0.1040 (2)0.6129 (5)0.25494 (6)0.0621 (7)
H6−0.17180.54360.26590.075*
C7−0.0295 (3)0.8158 (5)0.26846 (6)0.0660 (7)
H7−0.04620.88460.28860.079*
C80.0708 (3)0.9179 (5)0.25205 (6)0.0695 (7)
H80.12241.05510.26120.083*
C90.0951 (2)0.8179 (4)0.22210 (5)0.0545 (6)
H90.16240.88970.21110.065*
C100.25901 (18)0.4539 (4)0.11441 (5)0.0409 (5)
H10A0.28980.63270.11430.049*
H10B0.23090.40330.09190.049*
C110.37272 (18)0.2810 (4)0.12835 (4)0.0354 (5)
C120.3565 (2)0.0878 (4)0.15098 (5)0.0452 (5)
H120.27380.06430.15860.054*
C130.4616 (2)−0.0693 (4)0.16222 (5)0.0499 (6)
H130.4518−0.20010.17740.060*
C140.58170 (19)−0.0273 (4)0.15031 (5)0.0435 (5)
C150.4985 (2)0.3043 (4)0.11817 (5)0.0457 (5)
H150.51120.43360.10300.055*
C160.01583 (19)0.0825 (4)0.10273 (5)0.0413 (5)
C17−0.15751 (19)−0.1981 (4)0.07291 (5)0.0417 (5)
C18−0.0756 (2)−0.3663 (4)0.05794 (5)0.0464 (5)
H180.0164−0.36120.06370.056*
C19−0.1289 (2)−0.5423 (4)0.03440 (5)0.0486 (5)
H19−0.0725−0.65320.02450.058*
C20−0.2651 (2)−0.5540 (4)0.02558 (5)0.0462 (5)
C21−0.3474 (2)−0.3877 (5)0.04087 (5)0.0540 (6)
H21−0.4395−0.39500.03530.065*
C22−0.2944 (2)−0.2126 (4)0.06405 (5)0.0521 (6)
H22−0.3511−0.10210.07400.062*
C23−0.2494 (2)−0.8951 (5)−0.01383 (6)0.0588 (6)
H23A−0.2020−1.01040.00220.071*
H23B−0.1844−0.8044−0.02540.071*
C24−0.3440 (3)−1.0481 (6)−0.03759 (6)0.0780 (8)
H24A−0.4154−1.1156−0.02640.117*
H24B−0.2969−1.1896−0.04630.117*
H24C−0.3802−0.9367−0.05520.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0448 (3)0.0661 (4)0.0967 (5)0.0083 (3)0.0017 (3)0.0136 (4)
O10.0435 (9)0.0673 (11)0.0702 (11)−0.0103 (8)0.0162 (8)−0.0280 (9)
O20.0513 (9)0.0624 (10)0.0624 (10)−0.0076 (8)0.0004 (7)−0.0262 (8)
N10.0388 (9)0.0392 (10)0.0424 (10)−0.0022 (8)0.0045 (7)−0.0058 (8)
N20.0367 (9)0.0396 (10)0.0387 (9)−0.0042 (8)0.0063 (7)−0.0059 (8)
N30.0407 (10)0.0492 (11)0.0549 (11)−0.0024 (9)0.0119 (8)−0.0025 (9)
N40.0378 (9)0.0557 (11)0.0430 (10)−0.0096 (8)0.0068 (7)−0.0140 (9)
C10.0320 (10)0.0398 (12)0.0431 (12)0.0012 (9)0.0028 (9)−0.0005 (10)
C20.0333 (11)0.0481 (13)0.0446 (12)−0.0057 (10)0.0043 (9)−0.0059 (10)
C30.0320 (10)0.0415 (12)0.0403 (11)−0.0030 (9)0.0013 (9)−0.0033 (9)
C40.0369 (11)0.0400 (12)0.0408 (11)0.0063 (9)0.0011 (9)−0.0026 (9)
C50.0520 (13)0.0550 (14)0.0461 (13)−0.0029 (11)0.0076 (10)−0.0045 (11)
C60.0677 (16)0.0717 (17)0.0502 (14)0.0057 (14)0.0210 (12)0.0006 (13)
C70.0872 (19)0.0653 (17)0.0466 (14)0.0106 (15)0.0123 (13)−0.0111 (13)
C80.0876 (19)0.0611 (17)0.0595 (16)−0.0088 (15)0.0065 (14)−0.0214 (13)
C90.0589 (14)0.0545 (15)0.0510 (14)−0.0081 (12)0.0104 (11)−0.0106 (12)
C100.0406 (11)0.0427 (12)0.0406 (12)−0.0054 (10)0.0101 (9)−0.0014 (10)
C110.0357 (11)0.0351 (11)0.0359 (11)−0.0049 (9)0.0057 (8)−0.0059 (9)
C120.0369 (12)0.0518 (14)0.0479 (12)−0.0053 (10)0.0095 (9)0.0053 (11)
C130.0469 (13)0.0509 (14)0.0517 (13)−0.0037 (11)0.0048 (10)0.0130 (11)
C140.0351 (11)0.0435 (13)0.0508 (13)−0.0016 (9)0.0006 (9)−0.0057 (11)
C150.0461 (13)0.0454 (13)0.0471 (13)−0.0039 (10)0.0129 (10)0.0043 (10)
C160.0391 (12)0.0418 (12)0.0427 (12)−0.0047 (10)0.0032 (9)−0.0041 (10)
C170.0436 (12)0.0447 (13)0.0366 (11)−0.0090 (10)0.0032 (9)−0.0046 (10)
C180.0388 (12)0.0456 (13)0.0528 (13)−0.0020 (10)−0.0040 (10)−0.0053 (11)
C190.0488 (13)0.0446 (13)0.0520 (13)0.0016 (11)0.0034 (10)−0.0096 (11)
C200.0485 (13)0.0457 (13)0.0437 (12)−0.0117 (11)0.0019 (10)−0.0092 (10)
C210.0366 (12)0.0693 (16)0.0562 (14)−0.0104 (11)0.0048 (10)−0.0195 (12)
C220.0412 (12)0.0626 (15)0.0536 (14)−0.0070 (11)0.0105 (10)−0.0195 (12)
C230.0591 (14)0.0627 (16)0.0562 (14)−0.0098 (13)0.0135 (11)−0.0187 (12)
C240.0737 (17)0.092 (2)0.0695 (17)−0.0161 (16)0.0130 (13)−0.0413 (16)

Geometric parameters (Å, °)

Cl1—C141.736 (2)C9—H90.9300
O1—C161.226 (2)C10—C111.510 (3)
O2—C201.366 (2)C10—H10A0.9700
O2—C231.427 (2)C10—H10B0.9700
N1—C11.342 (2)C11—C121.381 (3)
N1—N21.351 (2)C11—C151.382 (3)
N2—C31.367 (2)C12—C131.369 (3)
N2—C101.458 (2)C12—H120.9300
N3—C141.322 (3)C13—C141.371 (3)
N3—C151.339 (3)C13—H130.9300
N4—C161.349 (2)C15—H150.9300
N4—C171.421 (2)C17—C181.385 (3)
N4—H40.8600C17—C221.388 (3)
C1—C21.401 (3)C18—C191.386 (3)
C1—C41.475 (3)C18—H180.9300
C2—C31.370 (3)C19—C201.379 (3)
C2—H20.9300C19—H190.9300
C3—C161.485 (3)C20—C211.388 (3)
C4—C51.386 (3)C21—C221.372 (3)
C4—C91.390 (3)C21—H210.9300
C5—C61.383 (3)C22—H220.9300
C5—H50.9300C23—C241.506 (3)
C6—C71.365 (3)C23—H23A0.9700
C6—H60.9300C23—H23B0.9700
C7—C81.379 (3)C24—H24A0.9600
C7—H70.9300C24—H24B0.9600
C8—C91.378 (3)C24—H24C0.9600
C8—H80.9300
C20—O2—C23118.55 (17)C13—C12—C11120.33 (18)
C1—N1—N2105.24 (15)C13—C12—H12119.8
N1—N2—C3111.98 (14)C11—C12—H12119.8
N1—N2—C10117.37 (15)C12—C13—C14117.8 (2)
C3—N2—C10129.97 (16)C12—C13—H13121.1
C14—N3—C15116.06 (17)C14—C13—H13121.1
C16—N4—C17126.88 (17)N3—C14—C13124.61 (19)
C16—N4—H4116.6N3—C14—Cl1116.05 (15)
C17—N4—H4116.6C13—C14—Cl1119.34 (17)
N1—C1—C2110.48 (17)N3—C15—C11124.67 (19)
N1—C1—C4120.47 (17)N3—C15—H15117.7
C2—C1—C4129.03 (17)C11—C15—H15117.7
C3—C2—C1106.18 (17)O1—C16—N4123.54 (18)
C3—C2—H2126.9O1—C16—C3121.32 (17)
C1—C2—H2126.9N4—C16—C3115.13 (17)
N2—C3—C2106.11 (16)C18—C17—C22118.31 (19)
N2—C3—C16122.22 (16)C18—C17—N4123.88 (18)
C2—C3—C16131.48 (17)C22—C17—N4117.81 (18)
C5—C4—C9117.98 (19)C17—C18—C19120.80 (19)
C5—C4—C1120.42 (18)C17—C18—H18119.6
C9—C4—C1121.61 (18)C19—C18—H18119.6
C6—C5—C4120.8 (2)C20—C19—C18120.46 (19)
C6—C5—H5119.6C20—C19—H19119.8
C4—C5—H5119.6C18—C19—H19119.8
C7—C6—C5120.5 (2)O2—C20—C19125.40 (19)
C7—C6—H6119.7O2—C20—C21115.80 (18)
C5—C6—H6119.7C19—C20—C21118.78 (19)
C6—C7—C8119.5 (2)C22—C21—C20120.72 (19)
C6—C7—H7120.3C22—C21—H21119.6
C8—C7—H7120.3C20—C21—H21119.6
C9—C8—C7120.4 (2)C21—C22—C17120.9 (2)
C9—C8—H8119.8C21—C22—H22119.5
C7—C8—H8119.8C17—C22—H22119.5
C8—C9—C4120.8 (2)O2—C23—C24107.08 (19)
C8—C9—H9119.6O2—C23—H23A110.3
C4—C9—H9119.6C24—C23—H23A110.3
N2—C10—C11111.72 (16)O2—C23—H23B110.3
N2—C10—H10A109.3C24—C23—H23B110.3
C11—C10—H10A109.3H23A—C23—H23B108.6
N2—C10—H10B109.3C23—C24—H24A109.5
C11—C10—H10B109.3C23—C24—H24B109.5
H10A—C10—H10B107.9H24A—C24—H24B109.5
C12—C11—C15116.50 (18)C23—C24—H24C109.5
C12—C11—C10122.38 (16)H24A—C24—H24C109.5
C15—C11—C10121.09 (18)H24B—C24—H24C109.5
C1—N1—N2—C3−0.8 (2)C11—C12—C13—C140.1 (3)
C1—N1—N2—C10−172.37 (16)C15—N3—C14—C130.2 (3)
N2—N1—C1—C20.2 (2)C15—N3—C14—Cl1−179.67 (15)
N2—N1—C1—C4178.97 (16)C12—C13—C14—N3−0.2 (3)
N1—C1—C2—C30.5 (2)C12—C13—C14—Cl1179.70 (16)
C4—C1—C2—C3−178.14 (19)C14—N3—C15—C11−0.2 (3)
N1—N2—C3—C21.2 (2)C12—C11—C15—N30.1 (3)
C10—N2—C3—C2171.32 (18)C10—C11—C15—N3−178.05 (18)
N1—N2—C3—C16−174.30 (17)C17—N4—C16—O10.5 (3)
C10—N2—C3—C16−4.1 (3)C17—N4—C16—C3−178.72 (18)
C1—C2—C3—N2−1.0 (2)N2—C3—C16—O118.9 (3)
C1—C2—C3—C16173.9 (2)C2—C3—C16—O1−155.2 (2)
N1—C1—C4—C5−171.48 (18)N2—C3—C16—N4−161.82 (18)
C2—C1—C4—C57.0 (3)C2—C3—C16—N424.0 (3)
N1—C1—C4—C98.7 (3)C16—N4—C17—C1819.0 (3)
C2—C1—C4—C9−172.8 (2)C16—N4—C17—C22−161.1 (2)
C9—C4—C5—C60.4 (3)C22—C17—C18—C190.8 (3)
C1—C4—C5—C6−179.4 (2)N4—C17—C18—C19−179.33 (19)
C4—C5—C6—C7−0.6 (4)C17—C18—C19—C20−0.4 (3)
C5—C6—C7—C80.1 (4)C23—O2—C20—C193.9 (3)
C6—C7—C8—C90.6 (4)C23—O2—C20—C21−177.9 (2)
C7—C8—C9—C4−0.7 (4)C18—C19—C20—O2177.8 (2)
C5—C4—C9—C80.2 (3)C18—C19—C20—C21−0.4 (3)
C1—C4—C9—C8−180.0 (2)O2—C20—C21—C22−177.6 (2)
N1—N2—C10—C1180.0 (2)C19—C20—C21—C220.8 (3)
C3—N2—C10—C11−89.7 (2)C20—C21—C22—C17−0.3 (4)
N2—C10—C11—C1214.6 (3)C18—C17—C22—C21−0.5 (3)
N2—C10—C11—C15−167.36 (17)N4—C17—C22—C21179.7 (2)
C15—C11—C12—C130.0 (3)C20—O2—C23—C24178.38 (19)
C10—C11—C12—C13178.07 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10B···O10.972.352.876 (3)114
C18—H18···O10.932.312.861 (3)118
C12—H12···Cg10.932.743.354 (2)125
N4—H4···N3i0.862.593.406 (2)159
C23—H23A···Cg2ii0.972.713.571 (3)149

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2246).

References

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