4-(4-Fluoro­phen­yl)-3-(pyridin-4-yl)-1-(2,4,6-trichloro­phen­yl)-1H-pyrazol-5-amine

Abu Thaher, B.; Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536812033569

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2603

doi:10.1107/S1600536812033569

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4-(4-Fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine

Bassam Abu Thaher,^a Pierre Koch,^b Dieter Schollmeyer ^c and Stefan Laufer ^b ^*

^aFaculty of Science, Chemistry Department, Islamic University of Gaza, Gaza Strip, Palestinian Territories, ^bInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^cDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 24 July 2012; accepted 25 July 2012; online 1 August 2012)

In the title compound, C₂₀H₁₂Cl₃FN₄, the pyrazole ring forms dihedral angles of 47.51 (9), 47.37 (9) and 74.37 (9)° with the directly attached 4-fluorophenyl, pyridine and 2,4,6-trichlorophenyl rings, respectively. Only one of the two amino H atoms is involved in hydrogen bonding. The crystal packing is characterized by N—H⋯N hydrogen bonds, which result in infinite chains parallel to the c axis.

Related literature

For the inhibitory activity and preparation of the title compound, see: Abu Thaher et al. (2012a ). For related structures, see: Abu Thaher et al. (2012b ,c ,d ,e ).

Experimental

Crystal data

C₂₀H₁₂Cl₃FN₄
M_r = 433.69
Triclinic, $[P \overline 1]$
a = 10.2487 (5) Å
b = 10.4643 (5) Å
c = 10.5489 (5) Å
α = 109.2377 (10)°
β = 111.4008 (10)°
γ = 98.0304 (11)°
V = 950.03 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 173 K
0.33 × 0.28 × 0.07 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.687, T_max = 0.746
21201 measured reflections
4517 independent reflections
3864 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.079
S = 1.03
4517 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N22ⁱ	0.90	2.17	3.0275 (17)	157
Symmetry code: (i) x, y, z+1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812033569/bt5984sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033569/bt5984Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812033569/bt5984Isup3.cml

checkCIF report

Comment top

The regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine changes the inhibitory profile from p38α MAP kinase to kinases relevant in cancer (Abu Thaher et al. 2012a). Recently, we reported similar crystal structures (Abu Thaher et al. 2012b,c,d,e). In the crystal structure of the title compound (Fig. 1), the pyrazole ring forms dihedral angels of 47.51 (9)°, 47.37 (9)°, 74.37 (9)° with the 4-fluorophenyl, pyridine and 2,4,6-trichlorophenyl rings, respectively. The 4-fluorophenyl ring encloses dihedral angels of 64.25 (8)° and 66.11 (8)° toward the pyridine and 2,4,6-trichlorophenyl rings, respectively. The pyridine ring is orientated at a dihedral angle of 78.99 (8)° toward the 2,4,6-trichlorophenyl ring. The crystal packing shows that the amino function acts as a hydrogen bond donor of an intermolecular hydrogen bond to the nitrogen atom (N22) of the pyridine ring. The length of the hydrogen bond is 2.17 Å (Table 1) and forms an infinite chain parallel to the c-axis.

Related literature top

For the inhibitory activity and preparation of the title compound, see: Abu Thaher et al. (2012a). For related structures, see: Abu Thaher et al. (2012b,c,d,e).

Experimental top

LDA (20 mmol) was added to dry THF (30 ml) in a three neck flask and cooled to 195 K. 4-Fluorophenylacetonitrile (14 mmol) in THF (10 ml) was added dropwise and the reaction was left stirring for 45 min. N-(2,4,6-trichlorophenyl)pyridine-4-carbohydrazonoyl chloride (5 mmol) was added slowly portionwise to the reaction. After about 1.0 h, the reaction was finished and left stirring to reach room temperature. Water (50 ml) was added to the reaction mixture and extracted with ethyl acetate (2x 50 mL). The organic layer was dried over Na₂SO₄. The organic layer was concentrated to about 5 ml and left overnight. The title compound was precipitated as a pale brown solid, filtered out, washed with petroleum ether. Yield 35%. The crystals for structure determination were obtained from recrystallization of the product from hot ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size.

4-(4-Fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H- pyrazol-5-amine top

Crystal data top

C₂₀H₁₂Cl₃FN₄	Z = 2
M_r = 433.69	F(000) = 440
Triclinic, P1	D_x = 1.516 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2487 (5) Å	Cell parameters from 7293 reflections
b = 10.4643 (5) Å	θ = 2.2–27.7°
c = 10.5489 (5) Å	µ = 0.51 mm⁻¹
α = 109.2377 (10)°	T = 173 K
β = 111.4008 (10)°	Plate, colourless
γ = 98.0304 (11)°	0.33 × 0.28 × 0.07 mm
V = 950.03 (8) Å³

Data collection top

Bruker SMART APEXII diffractometer	4517 independent reflections
Radiation source: sealed Tube	3864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
CCD scan	θ_max = 27.8°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
T_min = 0.687, T_max = 0.746	k = −13→13
21201 measured reflections	l = −13→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0335P)² + 0.4497P] where P = (F_o² + 2F_c²)/3
4517 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₀H₁₂Cl₃FN₄	γ = 98.0304 (11)°
M_r = 433.69	V = 950.03 (8) Å³
Triclinic, P1	Z = 2
a = 10.2487 (5) Å	Mo Kα radiation
b = 10.4643 (5) Å	µ = 0.51 mm⁻¹
c = 10.5489 (5) Å	T = 173 K
α = 109.2377 (10)°	0.33 × 0.28 × 0.07 mm
β = 111.4008 (10)°

Data collection top

Bruker SMART APEXII diffractometer	4517 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3864 reflections with I > 2σ(I)
T_min = 0.687, T_max = 0.746	R_int = 0.029
21201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
4517 reflections	Δρ_min = −0.33 e Å⁻³
253 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

	x	y	z	U_iso*/U_eq
Cl1	1.11579 (4)	0.81835 (4)	0.49931 (4)	0.03113 (10)
Cl2	0.55419 (4)	0.70476 (4)	0.42446 (4)	0.03333 (10)
Cl3	0.97212 (5)	1.14538 (4)	0.90748 (5)	0.04454 (13)
F1	0.50004 (11)	−0.13075 (9)	−0.22515 (12)	0.0397 (2)
N1	0.79475 (14)	0.65783 (12)	0.33280 (12)	0.0233 (3)
N2	0.78815 (13)	0.68969 (12)	0.21373 (12)	0.0218 (2)
C3	0.75032 (15)	0.56326 (14)	0.10311 (14)	0.0195 (3)
C4	0.73201 (16)	0.44990 (14)	0.14668 (15)	0.0210 (3)
C5	0.76173 (16)	0.51568 (14)	0.29651 (15)	0.0225 (3)
N6	0.76393 (17)	0.46090 (14)	0.39766 (14)	0.0333 (3)
H6A	0.7576	0.5126	0.4816	0.050*
H6B	0.7212	0.3720	0.3571	0.050*
C7	0.83795 (16)	0.77123 (14)	0.47287 (14)	0.0212 (3)
C8	0.98371 (16)	0.85674 (15)	0.55896 (15)	0.0220 (3)
C9	1.02636 (16)	0.97336 (15)	0.69174 (15)	0.0241 (3)
H9	1.1252	1.0322	0.7475	0.029*
C10	0.92128 (17)	1.00187 (15)	0.74088 (16)	0.0260 (3)
C11	0.77596 (17)	0.92009 (15)	0.66037 (16)	0.0258 (3)
H11	0.7054	0.9417	0.6960	0.031*
C12	0.73591 (16)	0.80573 (15)	0.52632 (15)	0.0228 (3)
C13	0.67511 (15)	0.29689 (14)	0.05054 (15)	0.0203 (3)
C14	0.73867 (17)	0.19851 (16)	0.09215 (16)	0.0261 (3)
H14	0.8231	0.2304	0.1848	0.031*
C15	0.67967 (18)	0.05394 (16)	−0.00078 (18)	0.0293 (3)
H15	0.7226	−0.0129	0.0279	0.035*
C16	0.55864 (17)	0.01080 (15)	−0.13404 (17)	0.0274 (3)
C17	0.49321 (17)	0.10325 (16)	−0.18119 (16)	0.0272 (3)
H17	0.4102	0.0701	−0.2752	0.033*
C18	0.55209 (16)	0.24677 (15)	−0.08716 (16)	0.0235 (3)
H18	0.5077	0.3123	−0.1172	0.028*
C19	0.74226 (15)	0.55640 (14)	−0.04193 (14)	0.0192 (3)
C20	0.67214 (16)	0.63729 (15)	−0.10978 (15)	0.0224 (3)
H20	0.6215	0.6939	−0.0672	0.027*
C21	0.67723 (17)	0.63399 (16)	−0.24026 (16)	0.0264 (3)
H21	0.6265	0.6878	−0.2865	0.032*
N22	0.74904 (15)	0.55985 (14)	−0.30536 (14)	0.0290 (3)
C23	0.81503 (18)	0.48164 (17)	−0.23960 (17)	0.0292 (3)
H23	0.8670	0.4280	−0.2832	0.035*
C24	0.81216 (16)	0.47424 (15)	−0.11190 (16)	0.0242 (3)
H24	0.8574	0.4138	−0.0725	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03306 (19)	0.0364 (2)	0.02770 (18)	0.01592 (16)	0.01643 (15)	0.01189 (16)
Cl2	0.02807 (19)	0.0373 (2)	0.02116 (17)	−0.00504 (15)	0.00680 (14)	0.00688 (15)
Cl3	0.0481 (2)	0.0315 (2)	0.0318 (2)	−0.00855 (18)	0.02382 (19)	−0.01149 (17)
F1	0.0488 (6)	0.0173 (4)	0.0460 (6)	0.0034 (4)	0.0257 (5)	0.0021 (4)
N1	0.0368 (7)	0.0182 (6)	0.0127 (5)	0.0038 (5)	0.0108 (5)	0.0058 (4)
N2	0.0309 (6)	0.0211 (6)	0.0135 (5)	0.0046 (5)	0.0100 (5)	0.0083 (4)
C3	0.0231 (6)	0.0203 (6)	0.0141 (6)	0.0052 (5)	0.0082 (5)	0.0063 (5)
C4	0.0282 (7)	0.0196 (6)	0.0153 (6)	0.0060 (5)	0.0100 (5)	0.0073 (5)
C5	0.0320 (7)	0.0190 (6)	0.0163 (6)	0.0062 (6)	0.0109 (6)	0.0075 (5)
N6	0.0631 (9)	0.0211 (6)	0.0191 (6)	0.0100 (6)	0.0213 (6)	0.0094 (5)
C7	0.0319 (7)	0.0170 (6)	0.0127 (6)	0.0046 (5)	0.0088 (5)	0.0061 (5)
C8	0.0280 (7)	0.0227 (7)	0.0180 (6)	0.0088 (6)	0.0109 (5)	0.0103 (5)
C9	0.0259 (7)	0.0221 (7)	0.0189 (6)	0.0022 (6)	0.0077 (6)	0.0066 (5)
C10	0.0341 (8)	0.0197 (7)	0.0177 (6)	0.0015 (6)	0.0122 (6)	0.0020 (5)
C11	0.0313 (8)	0.0238 (7)	0.0222 (7)	0.0034 (6)	0.0158 (6)	0.0066 (6)
C12	0.0257 (7)	0.0219 (7)	0.0166 (6)	0.0000 (5)	0.0076 (5)	0.0078 (5)
C13	0.0280 (7)	0.0187 (6)	0.0176 (6)	0.0059 (5)	0.0139 (5)	0.0072 (5)
C14	0.0336 (8)	0.0258 (7)	0.0214 (7)	0.0107 (6)	0.0127 (6)	0.0111 (6)
C15	0.0410 (9)	0.0241 (7)	0.0341 (8)	0.0150 (7)	0.0227 (7)	0.0159 (6)
C16	0.0365 (8)	0.0164 (6)	0.0309 (8)	0.0038 (6)	0.0228 (7)	0.0045 (6)
C17	0.0292 (7)	0.0242 (7)	0.0224 (7)	0.0029 (6)	0.0113 (6)	0.0047 (6)
C18	0.0281 (7)	0.0208 (7)	0.0223 (7)	0.0073 (6)	0.0121 (6)	0.0088 (5)
C19	0.0217 (6)	0.0185 (6)	0.0135 (6)	0.0004 (5)	0.0071 (5)	0.0050 (5)
C20	0.0290 (7)	0.0210 (7)	0.0189 (6)	0.0070 (6)	0.0128 (6)	0.0079 (5)
C21	0.0360 (8)	0.0259 (7)	0.0194 (7)	0.0083 (6)	0.0128 (6)	0.0116 (6)
N22	0.0401 (7)	0.0291 (7)	0.0199 (6)	0.0067 (6)	0.0169 (5)	0.0098 (5)
C23	0.0367 (8)	0.0301 (8)	0.0247 (7)	0.0111 (6)	0.0194 (6)	0.0086 (6)
C24	0.0285 (7)	0.0251 (7)	0.0210 (7)	0.0091 (6)	0.0119 (6)	0.0102 (6)

Geometric parameters (Å, º) top

Cl1—C8	1.7310 (15)	C11—H11	0.9500
Cl2—C12	1.7266 (15)	C13—C18	1.3969 (19)
Cl3—C10	1.7289 (14)	C13—C14	1.398 (2)
F1—C16	1.3677 (16)	C14—C15	1.396 (2)
N1—C5	1.3649 (18)	C14—H14	0.9500
N1—N2	1.3833 (16)	C15—C16	1.368 (2)
N1—C7	1.4170 (16)	C15—H15	0.9500
N2—C3	1.3310 (17)	C16—C17	1.374 (2)
C3—C4	1.4190 (19)	C17—C18	1.390 (2)
C3—C19	1.4788 (18)	C17—H17	0.9500
C4—C5	1.3921 (18)	C18—H18	0.9500
C4—C13	1.4730 (18)	C19—C24	1.3918 (19)
C5—N6	1.3627 (18)	C19—C20	1.3925 (19)
N6—H6A	0.9044	C20—C21	1.3857 (19)
N6—H6B	0.8528	C20—H20	0.9500
C7—C12	1.394 (2)	C21—N22	1.339 (2)
C7—C8	1.399 (2)	C21—H21	0.9500
C8—C9	1.3856 (19)	N22—C23	1.340 (2)
C9—C10	1.383 (2)	C23—C24	1.385 (2)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.383 (2)	C24—H24	0.9500
C11—C12	1.3872 (19)

C5—N1—N2	112.70 (11)	C18—C13—C14	118.19 (13)
C5—N1—C7	128.89 (12)	C18—C13—C4	119.28 (12)
N2—N1—C7	118.37 (11)	C14—C13—C4	122.54 (13)
C3—N2—N1	103.52 (11)	C15—C14—C13	120.83 (14)
N2—C3—C4	112.95 (12)	C15—C14—H14	119.6
N2—C3—C19	118.76 (12)	C13—C14—H14	119.6
C4—C3—C19	128.15 (12)	C16—C15—C14	118.46 (14)
C5—C4—C3	104.41 (12)	C16—C15—H15	120.8
C5—C4—C13	127.41 (13)	C14—C15—H15	120.8
C3—C4—C13	127.71 (12)	F1—C16—C15	118.68 (14)
N6—C5—N1	122.51 (12)	F1—C16—C17	118.28 (14)
N6—C5—C4	131.05 (13)	C15—C16—C17	123.04 (13)
N1—C5—C4	106.42 (12)	C16—C17—C18	117.99 (14)
C5—N6—H6A	120.3	C16—C17—H17	121.0
C5—N6—H6B	113.1	C18—C17—H17	121.0
H6A—N6—H6B	117.0	C17—C18—C13	121.49 (13)
C12—C7—C8	117.70 (12)	C17—C18—H18	119.3
C12—C7—N1	121.29 (13)	C13—C18—H18	119.3
C8—C7—N1	120.93 (13)	C24—C19—C20	117.29 (12)
C9—C8—C7	121.78 (13)	C24—C19—C3	120.87 (12)
C9—C8—Cl1	118.35 (11)	C20—C19—C3	121.74 (12)
C7—C8—Cl1	119.86 (10)	C21—C20—C19	119.06 (13)
C10—C9—C8	118.23 (13)	C21—C20—H20	120.5
C10—C9—H9	120.9	C19—C20—H20	120.5
C8—C9—H9	120.9	N22—C21—C20	124.20 (14)
C9—C10—C11	122.19 (13)	N22—C21—H21	117.9
C9—C10—Cl3	119.16 (11)	C20—C21—H21	117.9
C11—C10—Cl3	118.65 (12)	C21—N22—C23	116.10 (13)
C10—C11—C12	118.28 (14)	N22—C23—C24	124.00 (14)
C10—C11—H11	120.9	N22—C23—H23	118.0
C12—C11—H11	120.9	C24—C23—H23	118.0
C11—C12—C7	121.79 (13)	C23—C24—C19	119.25 (14)
C11—C12—Cl2	118.38 (12)	C23—C24—H24	120.4
C7—C12—Cl2	119.83 (11)	C19—C24—H24	120.4

C5—N1—N2—C3	−0.07 (16)	C10—C11—C12—Cl2	−179.22 (12)
C7—N1—N2—C3	177.83 (12)	C8—C7—C12—C11	−0.3 (2)
N1—N2—C3—C4	0.03 (16)	N1—C7—C12—C11	−177.31 (13)
N1—N2—C3—C19	−175.96 (12)	C8—C7—C12—Cl2	179.62 (11)
N2—C3—C4—C5	0.02 (17)	N1—C7—C12—Cl2	2.64 (19)
C19—C3—C4—C5	175.55 (13)	C5—C4—C13—C18	127.95 (16)
N2—C3—C4—C13	172.59 (13)	C3—C4—C13—C18	−43.0 (2)
C19—C3—C4—C13	−11.9 (2)	C5—C4—C13—C14	−51.4 (2)
N2—N1—C5—N6	178.89 (14)	C3—C4—C13—C14	137.65 (16)
C7—N1—C5—N6	1.3 (2)	C18—C13—C14—C15	−0.7 (2)
N2—N1—C5—C4	0.09 (17)	C4—C13—C14—C15	178.67 (14)
C7—N1—C5—C4	−177.54 (14)	C13—C14—C15—C16	0.4 (2)
C3—C4—C5—N6	−178.73 (16)	C14—C15—C16—F1	−179.70 (13)
C13—C4—C5—N6	8.7 (3)	C14—C15—C16—C17	0.6 (2)
C3—C4—C5—N1	−0.07 (16)	F1—C16—C17—C18	179.13 (13)
C13—C4—C5—N1	−172.66 (14)	C15—C16—C17—C18	−1.1 (2)
C5—N1—C7—C12	−77.8 (2)	C16—C17—C18—C13	0.8 (2)
N2—N1—C7—C12	104.65 (16)	C14—C13—C18—C17	0.1 (2)
C5—N1—C7—C8	105.30 (18)	C4—C13—C18—C17	−179.29 (13)
N2—N1—C7—C8	−72.23 (18)	N2—C3—C19—C24	130.10 (15)
C12—C7—C8—C9	−1.0 (2)	C4—C3—C19—C24	−45.2 (2)
N1—C7—C8—C9	175.96 (13)	N2—C3—C19—C20	−46.22 (19)
C12—C7—C8—Cl1	179.43 (11)	C4—C3—C19—C20	138.48 (15)
N1—C7—C8—Cl1	−3.59 (18)	C24—C19—C20—C21	−1.0 (2)
C7—C8—C9—C10	1.9 (2)	C3—C19—C20—C21	175.42 (13)
Cl1—C8—C9—C10	−178.53 (11)	C19—C20—C21—N22	−1.7 (2)
C8—C9—C10—C11	−1.5 (2)	C20—C21—N22—C23	2.2 (2)
C8—C9—C10—Cl3	179.15 (11)	C21—N22—C23—C24	0.1 (2)
C9—C10—C11—C12	0.2 (2)	N22—C23—C24—C19	−2.7 (2)
Cl3—C10—C11—C12	179.56 (11)	C20—C19—C24—C23	3.1 (2)
C10—C11—C12—C7	0.7 (2)	C3—C19—C24—C23	−173.41 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N22ⁱ	0.90	2.17	3.0275 (17)	157

Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂Cl₃FN₄
M_r	433.69
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	10.2487 (5), 10.4643 (5), 10.5489 (5)
α, β, γ (°)	109.2377 (10), 111.4008 (10), 98.0304 (11)
V (Å³)	950.03 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.33 × 0.28 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.687, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	21201, 4517, 3864
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 1.03
No. of reflections	4517
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N22ⁱ	0.90	2.17	3.0275 (17)	157

Symmetry code: (i) x, y, z+1.

Acknowledgements

BAT thanks the Alexander von Humboldt-Foundation for funding.

References

Abu Thaher, B., Arnsmann, M., Totzke, F., Ehlert, J. E., Kubbutat, M. H. G., Schächtele, C., Zimmermann, M. O., Koch, P., Boeckler, F. M. & Laufer, S. A. (2012a). J. Med. Chem. 55, 961–965. Web of Science CAS PubMed Google Scholar
Abu Thaher, B., Koch, P., Schollmeyer, D. & Laufer, S. (2012b). Acta Cryst. E68, o632. CSD CrossRef IUCr Journals Google Scholar
Abu Thaher, B., Koch, P., Schollmeyer, D. & Laufer, S. (2012c). Acta Cryst. E68, o633. CSD CrossRef IUCr Journals Google Scholar
Abu Thaher, B., Koch, P., Schollmeyer, D. & Laufer, S. (2012d). Acta Cryst. E68, o917–o918. CSD CrossRef IUCr Journals Google Scholar
Abu Thaher, B., Koch, P., Schollmeyer, D. & Laufer, S. (2012e). Acta Cryst. E68, o935. CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page o2603

doi:10.1107/S1600536812033569

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

4-(4-Fluoro­phen­yl)-3-(pyridin-4-yl)-1-(2,4,6-tri­chloro­phen­yl)-1H-pyrazol-5-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine