1-[3-(4-Chloro-phen-yl)isoquinolin-1-yl]-3,5-diethyl-1H-pyrazole.

The title compound, C(22)H(20)ClN(3), is composed of a dialkyl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 55.8 (1)° between the pyrazole ring and and the isoquinoline ring system. The dihedral angle between the chloro-phenyl ring and the isoquinoline ring system is 28.3 (1)°.

Related literature

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001 ▶).

Experimental

Crystal data

C22H20ClN3

M = 361.86

Monoclinic,

a = 8.4484 (6) Å

b = 15.0386 (12) Å

c = 15.4894 (11) Å

β = 96.763 (1)°

V = 1954.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 290 K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.951, T max = 0.970

14613 measured reflections

3703 independent reflections

2235 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.177

S = 1.03

3703 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055731/bt5161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055731/bt5161Isup2.hkl

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

C22H20ClN3	F(000) = 760
Mr = 361.86	Dx = 1.230 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2329 reflections
a = 8.4484 (6) Å	θ = 2.6–20.1°
b = 15.0386 (12) Å	µ = 0.21 mm−1
c = 15.4894 (11) Å	T = 290 K
β = 96.763 (1)°	Block, colorless
V = 1954.3 (3) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Bruker SMART area-detector diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.951, Tmax = 0.970	k = −18→18
14613 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.081P)2 + 0.4577P] where P = (Fo2 + 2Fc2)/3
3703 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.04502 (15)	0.45817 (9)	0.90130 (7)	0.1233 (5)
N1	0.3419 (2)	0.36347 (13)	0.53000 (14)	0.0507 (5)
N2	0.3322 (3)	0.30349 (14)	0.39224 (14)	0.0567 (6)
N3	0.3354 (3)	0.34178 (16)	0.31188 (16)	0.0691 (7)
C1	0.4218 (3)	0.34365 (16)	0.46595 (17)	0.0508 (6)
C2	0.5882 (3)	0.35802 (16)	0.46517 (18)	0.0539 (7)
C3	0.6777 (4)	0.3266 (2)	0.4002 (2)	0.0708 (8)
H3	0.6272	0.2958	0.3526	0.085*
C4	0.8377 (4)	0.3411 (2)	0.4069 (3)	0.0842 (10)
H4	0.8964	0.3191	0.3645	0.101*
C5	0.9138 (4)	0.3887 (2)	0.4766 (3)	0.0838 (10)
H5	1.0228	0.3992	0.4797	0.101*
C6	0.8312 (3)	0.4201 (2)	0.5405 (2)	0.0740 (9)
H6	0.8841	0.4519	0.5867	0.089*
C7	0.6650 (3)	0.40456 (16)	0.53719 (19)	0.0561 (7)
C8	0.5763 (3)	0.42863 (17)	0.60411 (18)	0.0572 (7)
H8	0.6246	0.4608	0.6513	0.069*
C9	0.4196 (3)	0.40544 (16)	0.60104 (16)	0.0497 (6)
C10	0.3237 (3)	0.42168 (17)	0.67334 (17)	0.0527 (7)
C11	0.3598 (4)	0.48974 (19)	0.73263 (18)	0.0660 (8)
H11	0.4439	0.5280	0.7257	0.079*
C12	0.2736 (4)	0.5017 (2)	0.8014 (2)	0.0806 (9)
H12	0.2991	0.5477	0.8408	0.097*
C13	0.1495 (4)	0.4454 (2)	0.8118 (2)	0.0756 (9)
C14	0.1079 (4)	0.3787 (2)	0.7535 (2)	0.0753 (9)
H14	0.0224	0.3415	0.7603	0.090*
C15	0.1948 (3)	0.3675 (2)	0.68431 (19)	0.0654 (8)
H15	0.1664	0.3226	0.6442	0.078*
C16	0.3239 (8)	0.3364 (4)	0.1205 (3)	0.170 (2)
H16A	0.2865	0.3496	0.0609	0.254*
H16B	0.3950	0.2865	0.1229	0.254*
H16C	0.3792	0.3871	0.1468	0.254*
C17	0.1949 (6)	0.3162 (3)	0.1649 (2)	0.1121 (14)
H17A	0.1385	0.2663	0.1361	0.135*
H17B	0.1227	0.3666	0.1599	0.135*
C18	0.2325 (4)	0.2938 (2)	0.25986 (19)	0.0704 (8)
C19	0.1668 (4)	0.2265 (2)	0.30509 (19)	0.0678 (8)
H19	0.0936	0.1841	0.2820	0.081*
C20	0.2294 (3)	0.23392 (18)	0.38943 (19)	0.0580 (7)
C21	0.2030 (4)	0.1809 (2)	0.4678 (2)	0.0755 (9)
H21A	0.3054	0.1626	0.4973	0.091*
H21B	0.1518	0.2183	0.5074	0.091*
C23	0.1027 (5)	0.1005 (3)	0.4464 (3)	0.1153 (15)
H23A	0.0896	0.0689	0.4989	0.173*
H23B	0.1538	0.0626	0.4082	0.173*
H23C	0.0002	0.1183	0.4183	0.173*

	U11	U22	U33	U12	U13	U23
Cl1	0.1396 (10)	0.1493 (10)	0.0907 (8)	0.0002 (8)	0.0536 (7)	−0.0141 (7)
N1	0.0447 (12)	0.0527 (12)	0.0538 (13)	−0.0062 (10)	0.0020 (10)	−0.0004 (10)
N2	0.0556 (14)	0.0604 (14)	0.0539 (14)	−0.0113 (11)	0.0048 (11)	−0.0057 (11)
N3	0.0807 (18)	0.0707 (16)	0.0554 (15)	−0.0148 (13)	0.0055 (13)	0.0011 (12)
C1	0.0492 (16)	0.0455 (14)	0.0565 (17)	−0.0060 (11)	0.0009 (13)	0.0010 (12)
C2	0.0451 (15)	0.0481 (14)	0.0683 (18)	−0.0035 (12)	0.0062 (13)	0.0085 (13)
C3	0.063 (2)	0.0708 (19)	0.081 (2)	0.0019 (15)	0.0174 (17)	0.0037 (16)
C4	0.061 (2)	0.087 (2)	0.109 (3)	0.0079 (17)	0.027 (2)	0.010 (2)
C5	0.0443 (18)	0.088 (2)	0.120 (3)	−0.0014 (17)	0.012 (2)	0.027 (2)
C6	0.0460 (17)	0.077 (2)	0.095 (2)	−0.0096 (15)	−0.0072 (17)	0.0142 (18)
C7	0.0455 (15)	0.0492 (15)	0.0711 (18)	−0.0055 (12)	−0.0042 (14)	0.0141 (13)
C8	0.0540 (17)	0.0527 (15)	0.0609 (17)	−0.0079 (13)	−0.0097 (14)	0.0028 (13)
C9	0.0480 (16)	0.0459 (14)	0.0523 (16)	−0.0046 (12)	−0.0064 (12)	0.0045 (12)
C10	0.0516 (16)	0.0515 (15)	0.0523 (15)	0.0029 (12)	−0.0049 (12)	0.0064 (12)
C11	0.074 (2)	0.0614 (17)	0.0616 (18)	−0.0055 (15)	0.0018 (16)	−0.0036 (15)
C12	0.098 (3)	0.080 (2)	0.062 (2)	−0.0021 (19)	0.0049 (18)	−0.0152 (17)
C13	0.084 (2)	0.087 (2)	0.0566 (19)	0.0108 (19)	0.0129 (16)	0.0040 (17)
C14	0.070 (2)	0.084 (2)	0.073 (2)	−0.0059 (17)	0.0134 (17)	0.0072 (18)
C15	0.0614 (18)	0.0712 (19)	0.0627 (18)	−0.0079 (15)	0.0035 (15)	−0.0034 (14)
C16	0.183 (6)	0.225 (7)	0.097 (4)	−0.021 (5)	0.000 (4)	0.037 (4)
C17	0.162 (4)	0.105 (3)	0.071 (3)	−0.028 (3)	0.020 (3)	−0.007 (2)
C18	0.078 (2)	0.078 (2)	0.0541 (18)	−0.0048 (17)	0.0019 (16)	−0.0130 (16)
C19	0.0670 (19)	0.0709 (19)	0.065 (2)	−0.0160 (15)	0.0042 (15)	−0.0193 (16)
C20	0.0536 (16)	0.0571 (16)	0.0639 (18)	−0.0119 (13)	0.0100 (13)	−0.0113 (14)
C21	0.083 (2)	0.0689 (19)	0.076 (2)	−0.0276 (16)	0.0127 (17)	−0.0040 (16)
C23	0.142 (4)	0.096 (3)	0.109 (3)	−0.060 (3)	0.015 (3)	0.001 (2)

Cl1—C13	1.739 (3)	C11—H11	0.9300
N1—C1	1.299 (3)	C12—C13	1.372 (5)
N1—C9	1.368 (3)	C12—H12	0.9300
N2—C20	1.357 (3)	C13—C14	1.368 (4)
N2—N3	1.375 (3)	C14—C15	1.378 (4)
N2—C1	1.428 (3)	C14—H14	0.9300
N3—C18	1.327 (4)	C15—H15	0.9300
C1—C2	1.424 (4)	C16—C17	1.390 (6)
C2—C7	1.409 (4)	C16—H16A	0.9600
C2—C3	1.410 (4)	C16—H16B	0.9600
C3—C4	1.361 (4)	C16—H16C	0.9600
C3—H3	0.9300	C17—C18	1.505 (5)
C4—C5	1.389 (5)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.361 (4)	C18—C19	1.384 (4)
C5—H5	0.9300	C19—C20	1.355 (4)
C6—C7	1.418 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.491 (4)
C7—C8	1.396 (4)	C21—C23	1.491 (4)
C8—C9	1.364 (4)	C21—H21A	0.9700
C8—H8	0.9300	C21—H21B	0.9700
C9—C10	1.478 (4)	C23—H23A	0.9600
C10—C15	1.387 (4)	C23—H23B	0.9600
C10—C11	1.385 (4)	C23—H23C	0.9600
C11—C12	1.372 (4)
C1—N1—C9	118.5 (2)	C14—C13—Cl1	119.6 (3)
C20—N2—N3	112.0 (2)	C12—C13—Cl1	119.5 (3)
C20—N2—C1	129.0 (2)	C13—C14—C15	119.0 (3)
N3—N2—C1	118.8 (2)	C13—C14—H14	120.5
C18—N3—N2	103.9 (2)	C15—C14—H14	120.5
N1—C1—C2	125.1 (2)	C14—C15—C10	121.4 (3)
N1—C1—N2	115.7 (2)	C14—C15—H15	119.3
C2—C1—N2	119.3 (2)	C10—C15—H15	119.3
C7—C2—C3	119.8 (3)	C17—C16—H16A	109.5
C7—C2—C1	115.6 (3)	C17—C16—H16B	109.5
C3—C2—C1	124.6 (3)	H16A—C16—H16B	109.5
C4—C3—C2	120.2 (3)	C17—C16—H16C	109.5
C4—C3—H3	119.9	H16A—C16—H16C	109.5
C2—C3—H3	119.9	H16B—C16—H16C	109.5
C3—C4—C5	120.4 (3)	C16—C17—C18	116.5 (4)
C3—C4—H4	119.8	C16—C17—H17A	108.2
C5—C4—H4	119.8	C18—C17—H17A	108.2
C6—C5—C4	121.0 (3)	C16—C17—H17B	108.2
C6—C5—H5	119.5	C18—C17—H17B	108.2
C4—C5—H5	119.5	H17A—C17—H17B	107.3
C5—C6—C7	120.4 (3)	N3—C18—C19	111.3 (3)
C5—C6—H6	119.8	N3—C18—C17	121.3 (3)
C7—C6—H6	119.8	C19—C18—C17	127.4 (3)
C8—C7—C2	118.6 (2)	C20—C19—C18	107.1 (3)
C8—C7—C6	123.1 (3)	C20—C19—H19	126.5
C2—C7—C6	118.2 (3)	C18—C19—H19	126.5
C9—C8—C7	120.7 (3)	C19—C20—N2	105.7 (3)
C9—C8—H8	119.6	C19—C20—C21	131.5 (3)
C7—C8—H8	119.6	N2—C20—C21	122.9 (2)
C8—C9—N1	121.2 (3)	C23—C21—C20	112.8 (3)
C8—C9—C10	123.2 (2)	C23—C21—H21A	109.0
N1—C9—C10	115.6 (2)	C20—C21—H21A	109.0
C15—C10—C11	117.9 (3)	C23—C21—H21B	109.0
C15—C10—C9	120.3 (2)	C20—C21—H21B	109.0
C11—C10—C9	121.8 (3)	H21A—C21—H21B	107.8
C12—C11—C10	121.1 (3)	C21—C23—H23A	109.5
C12—C11—H11	119.5	C21—C23—H23B	109.5
C10—C11—H11	119.5	H23A—C23—H23B	109.5
C11—C12—C13	119.6 (3)	C21—C23—H23C	109.5
C11—C12—H12	120.2	H23A—C23—H23C	109.5
C13—C12—H12	120.2	H23B—C23—H23C	109.5
C14—C13—C12	121.0 (3)
C20—N2—N3—C18	−0.2 (3)	C8—C9—C10—C15	−152.8 (3)
C1—N2—N3—C18	−175.2 (2)	N1—C9—C10—C15	26.0 (3)
C9—N1—C1—C2	3.5 (4)	C8—C9—C10—C11	26.3 (4)
C9—N1—C1—N2	−177.3 (2)	N1—C9—C10—C11	−154.9 (2)
C20—N2—C1—N1	−49.0 (4)	C15—C10—C11—C12	1.8 (4)
N3—N2—C1—N1	125.1 (3)	C9—C10—C11—C12	−177.3 (3)
C20—N2—C1—C2	130.3 (3)	C10—C11—C12—C13	0.0 (5)
N3—N2—C1—C2	−55.7 (3)	C11—C12—C13—C14	−1.5 (5)
N1—C1—C2—C7	−5.9 (4)	C11—C12—C13—Cl1	177.7 (2)
N2—C1—C2—C7	174.9 (2)	C12—C13—C14—C15	1.3 (5)
N1—C1—C2—C3	171.8 (3)	Cl1—C13—C14—C15	−178.0 (2)
N2—C1—C2—C3	−7.3 (4)	C13—C14—C15—C10	0.6 (5)
C7—C2—C3—C4	0.0 (4)	C11—C10—C15—C14	−2.1 (4)
C1—C2—C3—C4	−177.7 (3)	C9—C10—C15—C14	177.0 (3)
C2—C3—C4—C5	−1.4 (5)	N2—N3—C18—C19	−0.6 (3)
C3—C4—C5—C6	1.4 (5)	N2—N3—C18—C17	177.6 (3)
C4—C5—C6—C7	0.2 (5)	C16—C17—C18—N3	44.6 (6)
C3—C2—C7—C8	−174.8 (2)	C16—C17—C18—C19	−137.5 (5)
C1—C2—C7—C8	3.0 (3)	N3—C18—C19—C20	1.2 (4)
C3—C2—C7—C6	1.5 (4)	C17—C18—C19—C20	−176.8 (3)
C1—C2—C7—C6	179.3 (2)	C18—C19—C20—N2	−1.2 (3)
C5—C6—C7—C8	174.6 (3)	C18—C19—C20—C21	179.6 (3)
C5—C6—C7—C2	−1.6 (4)	N3—N2—C20—C19	0.9 (3)
C2—C7—C8—C9	1.8 (4)	C1—N2—C20—C19	175.3 (3)
C6—C7—C8—C9	−174.3 (2)	N3—N2—C20—C21	−179.8 (3)
C7—C8—C9—N1	−4.5 (4)	C1—N2—C20—C21	−5.4 (4)
C7—C8—C9—C10	174.2 (2)	C19—C20—C21—C23	7.2 (5)
C1—N1—C9—C8	1.9 (3)	N2—C20—C21—C23	−171.8 (3)
C1—N1—C9—C10	−176.9 (2)