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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1077

5-(4-Chloro­phen­yl)-1-(2,4-di­chloro­phen­yl)-4-methyl-N-(3-pyridylmeth­yl)-1H-pyrazole-3-carboxamide

aBeijing Institute of Pharmacology and Toxicology, Beijing 100850, People's Republic of China
*Correspondence e-mail: hexinhua01@126.com

(Received 30 December 2008; accepted 10 April 2009; online 18 April 2009)

In the title compound, C23H17Cl3N4O, the benzene rings are oriented with respect to the pyrazole ring at dihedral angles of 39.9 (2) and 72.90 (13)° for the chloro­phenyl and di­chloro­phenyl rings, respectively. Inter­molecular C—H⋯N and C—H⋯Cl inter­actions are observed in the crystal packing.

Related literature

For general background to pyrazole derivatives and their biological activity, see: Srivastava et al. (2008[Srivastava, B. K., et al. (2008). Bioorg. Med. Chem. Lett. 18, 963-968.]); LoVerme et al. (2009[LoVerme, J., Duranti, A., Tontini, A., Spadoni, G., Mor, M., Rivara, S., Stella, N., Xu, C., Tarzia, G. & Piomelli, D. (2009). Bioorg. Med. Chem. Lett. 19, 639-643.]); Rinaldi-Carmona et al. (1994[Rinaldi-Carmona, M., Barth, F., Héaulme, M., Shire, D., Calandra, B., Congy, C., Martinez, S., Maruani, J., Néliat, G., Caput, D., Ferrara, P., Soubrié, P., Breliére, J. C. & LeFur, G. (1994). FEBS Lett. 350, 240-244.]). For the synthesis, see: Li et al. (2007[Li, S., Liu, M. J. & Zheng, Z. B. (2007). WO Patent WO2007079681.]).

[Scheme 1]

Experimental

Crystal data
  • C23H17Cl3N4O

  • Mr = 471.76

  • Monoclinic, P 21 /c

  • a = 9.0032 (4) Å

  • b = 20.1001 (8) Å

  • c = 11.4664 (5) Å

  • β = 92.003 (2)°

  • V = 2073.75 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 113 K

  • 0.26 × 0.20 × 0.18 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.888, Tmax = 0.921

  • 19184 measured reflections

  • 4914 independent reflections

  • 4152 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.06

  • 4914 reflections

  • 285 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.75 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯N4i 0.95 2.56 3.272 (2) 132
C7—H7⋯Cl2ii 0.95 2.84 3.5903 (15) 137
Symmetry codes: (i) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) and publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

Pyrazole derivatives have been found to be a novel class of cannabinoid CB1 receptor antagonists (Srivastava et al., 2008; LoVerme et al., 2009; Rinaldi-Carmona M. et al., 1994). The crystal structure of the title compound (IC50 =0.139nM at CB1) was analyzed by X-ray diffraction, for the purpose of studying its quantitative structure-activity relationship (QSAR).

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The benzene rings (C6—C11) and (C12—C17) are oriented at dihedral angles of 39.9 (2)° and 72.90 (13)°, respectively, with respect to the pyrazole ring.

In the crystal structure, the molecules are linked by intermolecular C17—H17···N4 and C7—H7···Cl2 interactions (Fig. 2).

Related literature top

For general background to pyrazole derivatives and their biological activity, see: Srivastava et al. (2008) ; LoVerme et al. (2009); Rinaldi-Carmona et al. (1994). For the synthesis, see: Li et al. (2007).

Experimental top

The title compound was synthesized according to the procedure of Li et al.(2007). Colorless single crystals were obtained by slow evaporation of a solution in ehtyl acetate.

Refinement top

The H atoms linked to the C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å (aromatic), 0.98Å (methyl), 0.99 Å (methylene) with Uiso(H) =1.2–1.5Ueq(C). H atoms of the amino group were located in a difference Fourier map and refined freely.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme and ellipsoids at the 30 % probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen bonds are indicated by dashed lines.
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-pyridylmethyl)- 1H-pyrazole-3-carboxamide top
Crystal data top
C23H17Cl3N4OF(000) = 968
Mr = 471.76Dx = 1.511 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
a = 9.0032 (4) ÅCell parameters from 4274 reflections
b = 20.1001 (8) Åθ = 1.8–27.9°
c = 11.4664 (5) ŵ = 0.47 mm1
β = 92.003 (2)°T = 113 K
V = 2073.75 (15) Å3Block, colorless
Z = 40.26 × 0.20 × 0.18 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
4914 independent reflections
Radiation source: rotating anode4152 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and ϕ scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2626
Tmin = 0.888, Tmax = 0.921l = 1515
19184 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.5347P]
where P = (Fo2 + 2Fc2)/3
4914 reflections(Δ/σ)max = 0.002
285 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C23H17Cl3N4OV = 2073.75 (15) Å3
Mr = 471.76Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.0032 (4) ŵ = 0.47 mm1
b = 20.1001 (8) ÅT = 113 K
c = 11.4664 (5) Å0.26 × 0.20 × 0.18 mm
β = 92.003 (2)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
4914 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
4152 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.921Rint = 0.034
19184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.75 e Å3
4914 reflectionsΔρmin = 0.38 e Å3
285 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
xyzUiso*/Ueq
Cl10.01811 (4)0.643967 (18)0.56112 (3)0.02233 (10)
Cl20.52709 (4)0.554267 (18)0.22278 (3)0.02014 (10)
Cl30.15192 (4)0.596113 (19)0.14473 (3)0.02088 (10)
O10.60926 (12)0.24050 (6)0.40372 (10)0.0235 (3)
N10.65174 (14)0.25624 (6)0.21143 (12)0.0177 (3)
H10.633 (2)0.2770 (10)0.1553 (17)0.023 (5)*
N20.47501 (14)0.36428 (6)0.20324 (11)0.0158 (3)
N30.38825 (14)0.41730 (6)0.22738 (11)0.0149 (3)
N41.09010 (16)0.18709 (7)0.40063 (13)0.0255 (3)
C10.59001 (16)0.27258 (7)0.31272 (14)0.0160 (3)
C20.49452 (15)0.33347 (7)0.30626 (13)0.0145 (3)
C30.41906 (16)0.36537 (7)0.39652 (13)0.0142 (3)
C40.35219 (16)0.42006 (7)0.34305 (13)0.0138 (3)
C50.40835 (18)0.34400 (8)0.52139 (13)0.0203 (3)
H5A0.49380.36140.56720.030*
H5B0.40800.29530.52560.030*
H5C0.31630.36140.55290.030*
C60.26488 (16)0.47476 (7)0.39330 (12)0.0135 (3)
C70.30933 (16)0.49932 (8)0.50303 (13)0.0159 (3)
H70.39270.48000.54320.019*
C80.23420 (17)0.55137 (7)0.55469 (13)0.0169 (3)
H80.26620.56790.62900.020*
C90.11196 (16)0.57867 (7)0.49587 (13)0.0155 (3)
C100.06310 (16)0.55496 (7)0.38774 (13)0.0155 (3)
H100.02150.57400.34880.019*
C110.13936 (16)0.50292 (7)0.33683 (13)0.0144 (3)
H110.10600.48630.26290.017*
C120.33945 (16)0.45989 (7)0.13373 (12)0.0143 (3)
C130.39214 (16)0.52489 (7)0.12519 (13)0.0144 (3)
C140.33693 (16)0.56739 (7)0.03826 (13)0.0154 (3)
H140.37210.61180.03250.019*
C150.22900 (16)0.54305 (7)0.03979 (12)0.0155 (3)
C160.17985 (17)0.47747 (7)0.03588 (13)0.0181 (3)
H160.10900.46130.09230.022*
C170.23618 (17)0.43610 (8)0.05187 (13)0.0172 (3)
H170.20370.39120.05570.021*
C180.74791 (16)0.19856 (7)0.19942 (14)0.0185 (3)
H18A0.75110.18670.11580.022*
H18B0.70400.16050.24080.022*
C190.95085 (18)0.18300 (8)0.35444 (15)0.0213 (3)
H190.87860.16070.39850.026*
C200.90543 (16)0.20918 (7)0.24668 (13)0.0158 (3)
C211.01070 (18)0.24347 (8)0.18393 (14)0.0200 (3)
H210.98440.26300.11060.024*
C221.15446 (18)0.24873 (8)0.23013 (15)0.0237 (3)
H221.22810.27210.18920.028*
C231.18931 (18)0.21935 (8)0.33690 (16)0.0254 (4)
H231.28890.22220.36660.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0286 (2)0.01416 (17)0.0247 (2)0.00408 (14)0.00882 (16)0.00229 (14)
Cl20.01844 (19)0.02230 (19)0.01936 (19)0.00254 (14)0.00415 (14)0.00143 (14)
Cl30.0230 (2)0.02238 (19)0.01701 (19)0.00224 (15)0.00231 (14)0.00519 (14)
O10.0245 (6)0.0209 (6)0.0252 (6)0.0074 (5)0.0007 (5)0.0043 (5)
N10.0171 (6)0.0151 (6)0.0208 (7)0.0055 (5)0.0006 (5)0.0016 (5)
N20.0145 (6)0.0130 (6)0.0199 (7)0.0034 (5)0.0021 (5)0.0005 (5)
N30.0163 (6)0.0135 (6)0.0151 (6)0.0048 (5)0.0021 (5)0.0009 (5)
N40.0232 (7)0.0239 (7)0.0290 (8)0.0020 (6)0.0049 (6)0.0042 (6)
C10.0110 (7)0.0131 (7)0.0239 (8)0.0007 (5)0.0010 (6)0.0006 (6)
C20.0108 (7)0.0132 (6)0.0194 (7)0.0009 (5)0.0002 (5)0.0004 (6)
C30.0113 (7)0.0139 (7)0.0172 (7)0.0002 (5)0.0016 (5)0.0003 (5)
C40.0127 (7)0.0150 (7)0.0136 (7)0.0003 (5)0.0001 (5)0.0006 (5)
C50.0229 (8)0.0208 (8)0.0170 (8)0.0047 (6)0.0015 (6)0.0028 (6)
C60.0126 (7)0.0136 (7)0.0144 (7)0.0001 (5)0.0024 (5)0.0010 (5)
C70.0124 (7)0.0202 (7)0.0151 (7)0.0006 (6)0.0000 (5)0.0007 (6)
C80.0166 (7)0.0186 (7)0.0154 (7)0.0036 (6)0.0016 (6)0.0025 (6)
C90.0165 (7)0.0103 (6)0.0201 (8)0.0010 (5)0.0075 (6)0.0006 (5)
C100.0137 (7)0.0139 (7)0.0190 (7)0.0010 (5)0.0020 (6)0.0033 (6)
C110.0148 (7)0.0146 (7)0.0139 (7)0.0006 (5)0.0004 (5)0.0004 (5)
C120.0156 (7)0.0149 (7)0.0128 (7)0.0050 (5)0.0037 (6)0.0011 (5)
C130.0123 (7)0.0173 (7)0.0138 (7)0.0017 (5)0.0017 (5)0.0028 (5)
C140.0170 (7)0.0142 (7)0.0153 (7)0.0006 (5)0.0034 (6)0.0002 (6)
C150.0168 (7)0.0171 (7)0.0127 (7)0.0039 (6)0.0024 (6)0.0017 (6)
C160.0188 (7)0.0198 (7)0.0157 (7)0.0001 (6)0.0011 (6)0.0019 (6)
C170.0188 (7)0.0142 (7)0.0188 (8)0.0004 (6)0.0023 (6)0.0020 (6)
C180.0152 (7)0.0142 (7)0.0262 (8)0.0031 (6)0.0004 (6)0.0041 (6)
C190.0194 (8)0.0181 (7)0.0265 (8)0.0005 (6)0.0015 (6)0.0041 (6)
C200.0154 (7)0.0110 (6)0.0212 (8)0.0033 (5)0.0012 (6)0.0037 (6)
C210.0238 (8)0.0174 (7)0.0190 (8)0.0003 (6)0.0029 (6)0.0015 (6)
C220.0198 (8)0.0235 (8)0.0284 (9)0.0049 (6)0.0073 (7)0.0030 (7)
C230.0168 (8)0.0247 (8)0.0344 (10)0.0002 (6)0.0033 (7)0.0044 (7)
Geometric parameters (Å, º) top
Cl1—C91.7437 (15)C8—H80.9500
Cl2—C131.7268 (15)C9—C101.386 (2)
Cl3—C151.7346 (15)C10—C111.391 (2)
O1—C11.2336 (19)C10—H100.9500
N1—C11.346 (2)C11—H110.9500
N1—C181.4565 (18)C12—C171.383 (2)
N1—H10.78 (2)C12—C131.395 (2)
N2—C21.3399 (19)C13—C141.391 (2)
N2—N31.3556 (16)C14—C151.387 (2)
N3—C41.3776 (19)C14—H140.9500
N3—C121.4303 (18)C15—C161.392 (2)
N4—C231.341 (2)C16—C171.388 (2)
N4—C191.346 (2)C16—H160.9500
C1—C21.496 (2)C17—H170.9500
C2—C31.412 (2)C18—C201.515 (2)
C3—C41.386 (2)C18—H18A0.9900
C3—C51.501 (2)C18—H18B0.9900
C4—C61.480 (2)C19—C201.391 (2)
C5—H5A0.9800C19—H190.9500
C5—H5B0.9800C20—C211.392 (2)
C5—H5C0.9800C21—C221.385 (2)
C6—C71.397 (2)C21—H210.9500
C6—C111.4019 (19)C22—C231.385 (2)
C7—C81.390 (2)C22—H220.9500
C7—H70.9500C23—H230.9500
C8—C91.384 (2)
C1—N1—C18122.73 (14)C10—C11—H11119.6
C1—N1—H1119.9 (14)C6—C11—H11119.6
C18—N1—H1117.3 (14)C17—C12—C13119.89 (13)
C2—N2—N3104.00 (12)C17—C12—N3118.96 (13)
N2—N3—C4112.65 (12)C13—C12—N3121.14 (13)
N2—N3—C12118.77 (12)C14—C13—C12120.77 (13)
C4—N3—C12128.47 (12)C14—C13—Cl2118.68 (11)
C23—N4—C19116.36 (15)C12—C13—Cl2120.55 (11)
O1—C1—N1123.54 (14)C15—C14—C13118.06 (13)
O1—C1—C2122.20 (14)C15—C14—H14121.0
N1—C1—C2114.26 (13)C13—C14—H14121.0
N2—C2—C3112.63 (13)C14—C15—C16121.99 (13)
N2—C2—C1118.63 (13)C14—C15—Cl3119.01 (11)
C3—C2—C1128.74 (13)C16—C15—Cl3119.00 (12)
C4—C3—C2104.40 (13)C17—C16—C15118.84 (14)
C4—C3—C5127.40 (13)C17—C16—H16120.6
C2—C3—C5128.16 (13)C15—C16—H16120.6
N3—C4—C3106.29 (13)C12—C17—C16120.33 (14)
N3—C4—C6123.44 (13)C12—C17—H17119.8
C3—C4—C6130.20 (13)C16—C17—H17119.8
C3—C5—H5A109.5N1—C18—C20113.96 (12)
C3—C5—H5B109.5N1—C18—H18A108.8
H5A—C5—H5B109.5C20—C18—H18A108.8
C3—C5—H5C109.5N1—C18—H18B108.8
H5A—C5—H5C109.5C20—C18—H18B108.8
H5B—C5—H5C109.5H18A—C18—H18B107.7
C7—C6—C11118.31 (13)N4—C19—C20124.54 (15)
C7—C6—C4118.28 (13)N4—C19—H19117.7
C11—C6—C4123.41 (13)C20—C19—H19117.7
C8—C7—C6121.43 (14)C19—C20—C21117.51 (14)
C8—C7—H7119.3C19—C20—C18120.44 (14)
C6—C7—H7119.3C21—C20—C18122.03 (14)
C9—C8—C7118.78 (14)C22—C21—C20118.94 (15)
C9—C8—H8120.6C22—C21—H21120.5
C7—C8—H8120.6C20—C21—H21120.5
C8—C9—C10121.46 (13)C21—C22—C23119.02 (15)
C8—C9—Cl1118.58 (12)C21—C22—H22120.5
C10—C9—Cl1119.96 (11)C23—C22—H22120.5
C9—C10—C11119.23 (13)N4—C23—C22123.58 (15)
C9—C10—H10120.4N4—C23—H23118.2
C11—C10—H10120.4C22—C23—H23118.2
C10—C11—C6120.77 (13)
C2—N2—N3—C40.44 (16)Cl1—C9—C10—C11179.90 (11)
C2—N2—N3—C12177.01 (12)C9—C10—C11—C60.4 (2)
C18—N1—C1—O10.1 (2)C7—C6—C11—C101.4 (2)
C18—N1—C1—C2179.79 (13)C4—C6—C11—C10179.03 (14)
N3—N2—C2—C31.05 (16)N2—N3—C12—C1769.79 (18)
N3—N2—C2—C1178.45 (12)C4—N3—C12—C17106.16 (17)
O1—C1—C2—N2177.73 (14)N2—N3—C12—C13111.38 (15)
N1—C1—C2—N22.13 (19)C4—N3—C12—C1372.7 (2)
O1—C1—C2—C32.9 (2)C17—C12—C13—C143.0 (2)
N1—C1—C2—C3177.28 (14)N3—C12—C13—C14175.77 (13)
N2—C2—C3—C41.25 (16)C17—C12—C13—Cl2177.12 (11)
C1—C2—C3—C4178.18 (14)N3—C12—C13—Cl24.06 (19)
N2—C2—C3—C5176.76 (14)C12—C13—C14—C150.4 (2)
C1—C2—C3—C53.8 (2)Cl2—C13—C14—C15179.75 (11)
N2—N3—C4—C30.31 (16)C13—C14—C15—C162.5 (2)
C12—N3—C4—C3175.84 (14)C13—C14—C15—Cl3176.98 (11)
N2—N3—C4—C6176.89 (13)C14—C15—C16—C172.8 (2)
C12—N3—C4—C67.0 (2)Cl3—C15—C16—C17176.73 (11)
C2—C3—C4—N30.89 (15)C13—C12—C17—C162.8 (2)
C5—C3—C4—N3177.14 (14)N3—C12—C17—C16176.05 (13)
C2—C3—C4—C6176.05 (14)C15—C16—C17—C120.1 (2)
C5—C3—C4—C65.9 (3)C1—N1—C18—C2078.52 (18)
N3—C4—C6—C7138.52 (15)C23—N4—C19—C200.6 (2)
C3—C4—C6—C738.0 (2)N4—C19—C20—C211.8 (2)
N3—C4—C6—C1141.9 (2)N4—C19—C20—C18176.56 (15)
C3—C4—C6—C11141.62 (16)N1—C18—C20—C19102.36 (17)
C11—C6—C7—C81.5 (2)N1—C18—C20—C2179.37 (18)
C4—C6—C7—C8178.89 (13)C19—C20—C21—C221.2 (2)
C6—C7—C8—C90.6 (2)C18—C20—C21—C22177.11 (14)
C7—C8—C9—C100.4 (2)C20—C21—C22—C230.4 (2)
C7—C8—C9—Cl1180.00 (11)C19—N4—C23—C221.3 (3)
C8—C9—C10—C110.5 (2)C21—C22—C23—N41.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N4i0.952.563.272 (2)132
C7—H7···Cl2ii0.952.843.5903 (15)137
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC23H17Cl3N4O
Mr471.76
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)9.0032 (4), 20.1001 (8), 11.4664 (5)
β (°) 92.003 (2)
V3)2073.75 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.47
Crystal size (mm)0.26 × 0.20 × 0.18
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.888, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections
19184, 4914, 4152
Rint0.034
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.06
No. of reflections4914
No. of parameters285
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.75, 0.38

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2004) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N4i0.952.563.272 (2)131.9
C7—H7···Cl2ii0.952.8393.5903 (15)136.7
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1, z+1.
 

Acknowledgements

We thank T. L. Liang for her fruitful help.

References

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First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
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First citationRinaldi-Carmona, M., Barth, F., Héaulme, M., Shire, D., Calandra, B., Congy, C., Martinez, S., Maruani, J., Néliat, G., Caput, D., Ferrara, P., Soubrié, P., Breliére, J. C. & LeFur, G. (1994). FEBS Lett. 350, 240–244.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSrivastava, B. K., et al. (2008). Bioorg. Med. Chem. Lett. 18, 963–968.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Volume 65| Part 5| May 2009| Page o1077
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