4-(4-Fluoro-phen-yl)-3-(pyridin-4-yl)-1-(2,4,6-trichloro-phen-yl)-1H-pyrazol-5-amine.

In the title compound, C(20)H(12)Cl(3)FN(4), the pyrazole ring forms dihedral angles of 47.51 (9), 47.37 (9) and 74.37 (9)° with the directly attached 4-fluoro-phenyl, pyridine and 2,4,6-trichloro-phenyl 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 = 433.69

Triclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.03

4517 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.33 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033569/bt5984sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812033569/bt5984Isup3.cml

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

C20H12Cl3FN4	Z = 2
Mr = 433.69	F(000) = 440
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0335P)2 + 0.4497P] where P = (Fo2 + 2Fc2)/3
4517 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .