1-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-phenyl-isoquinoline.

The mol-ecular conformation of the title compound, C(20)H(17)N(3), is stabilized by an intramolecular C-H⋯N inter-action. The crystal structure shows inter-molecular C-H⋯π inter-actions. The dihedral angle between the isoquinoline unit and the phenyl ring is 11.42 (1)° whereas the isoquinoline unit and the pendent dimethyl pryrazole unit form a dihedral angle of 50.1 (4)°. Furthermore, the angle between the mean plane of the phenyl ring and the dimethyl pyrazole unit is 47.3 (6)°.

Related literature

For general background to isoquinolines, see: Kametani et al. (1968 ▶); Broadhurst et al. (2001 ▶); Chao et al. (1999 ▶); Choudhury et al. (2002 ▶, 2006 ▶); Hathwar et al. (2008 ▶); Elguero et al. 2002 ▶).

Experimental

Crystal data

C20H17N3

M = 299.37

Orthorhombic,

a = 18.3294 (14) Å

b = 8.3139 (7) Å

c = 21.6532 (17) Å

V = 3299.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 290 K

0.18 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.995

22808 measured reflections

3065 independent reflections

2608 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.129

S = 1.14

3065 reflections

276 parameters

All H-atom parameters refined

Δρmax = 0.15 e Å−3

Δρmin = −0.15 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: CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024842/bt2974sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024842/bt2974Isup2.hkl

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

C20H17N3	F(000) = 1264
Mr = 299.37	Dx = 1.205 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1248 reflections
a = 18.3294 (14) Å	θ = 2.2–27.2°
b = 8.3139 (7) Å	µ = 0.07 mm−1
c = 21.6532 (17) Å	T = 290 K
V = 3299.7 (5) Å3	Block, colorless
Z = 8	0.18 × 0.11 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	3065 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→20
Tmin = 0.949, Tmax = 0.995	k = −10→10
22808 measured reflections	l = −26→24

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	All H-atom parameters refined
S = 1.14	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6765P] where P = (Fo2 + 2Fc2)/3
3065 reflections	(Δ/σ)max < 0.001
276 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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 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.

	x	y	z	Uiso*/Ueq
N1	0.09848 (7)	0.53396 (16)	0.26708 (6)	0.0490 (4)
N2	0.02198 (7)	0.52682 (18)	0.18301 (6)	0.0538 (4)
C1	0.08768 (9)	0.47659 (19)	0.21175 (7)	0.0470 (4)
C8	0.13594 (9)	0.37101 (19)	0.18015 (7)	0.0477 (4)
C3	0.21303 (10)	0.3989 (2)	0.27066 (8)	0.0525 (4)
C9	0.20196 (9)	0.3351 (2)	0.21115 (8)	0.0491 (4)
C2	0.16088 (9)	0.4924 (2)	0.29813 (8)	0.0485 (4)
C10	0.16626 (9)	0.5586 (2)	0.36145 (8)	0.0533 (4)
C4	0.25285 (11)	0.2347 (2)	0.18064 (9)	0.0611 (5)
C16	−0.04605 (9)	0.5383 (2)	0.20820 (9)	0.0555 (5)
C7	0.12169 (11)	0.3011 (2)	0.12208 (8)	0.0597 (5)
N3	0.02521 (8)	0.5925 (2)	0.12480 (7)	0.0677 (5)
C20	−0.06494 (13)	0.4719 (3)	0.26970 (12)	0.0742 (6)
C5	0.23812 (12)	0.1701 (3)	0.12503 (9)	0.0705 (6)
C11	0.22045 (12)	0.5099 (3)	0.40250 (9)	0.0673 (6)
C15	0.11577 (12)	0.6709 (3)	0.38203 (9)	0.0698 (6)
C6	0.17167 (12)	0.2015 (3)	0.09549 (10)	0.0699 (6)
C12	0.22252 (14)	0.5691 (3)	0.46184 (10)	0.0819 (7)
C18	−0.04247 (12)	0.6423 (3)	0.11454 (9)	0.0723 (6)
C13	0.17137 (16)	0.6770 (3)	0.48194 (11)	0.0876 (8)
C17	−0.08729 (12)	0.6106 (3)	0.16449 (10)	0.0700 (6)
C14	0.11810 (15)	0.7294 (3)	0.44162 (11)	0.0855 (7)
C19	−0.06113 (15)	0.7207 (4)	0.05432 (11)	0.1147 (10)
H19A	−0.0312	0.8144	0.0487	0.172*
H19B	−0.1116	0.7517	0.0545	0.172*
H19C	−0.0526	0.6464	0.0212	0.172*
H3	0.2583 (10)	0.378 (2)	0.2919 (8)	0.064 (5)*
H7	0.0783 (10)	0.330 (2)	0.1015 (8)	0.070 (6)*
H4	0.2958 (10)	0.212 (2)	0.2010 (9)	0.065 (5)*
H11	0.2580 (13)	0.431 (3)	0.3893 (10)	0.090 (7)*
H5	0.2750 (11)	0.100 (3)	0.1032 (9)	0.080 (6)*
H15	0.0784 (11)	0.712 (3)	0.3537 (9)	0.079 (6)*
H20C	−0.1161 (15)	0.482 (3)	0.2777 (10)	0.106 (8)*
H17	−0.1358 (12)	0.633 (2)	0.1678 (9)	0.073 (6)*
H20B	−0.0531 (14)	0.356 (4)	0.2713 (12)	0.128 (10)*
H14	0.0827 (11)	0.809 (3)	0.4543 (10)	0.083 (7)*
H12	0.2612 (13)	0.529 (3)	0.4907 (11)	0.104 (8)*
H20A	−0.0422 (13)	0.531 (3)	0.3038 (11)	0.098 (8)*
H6	0.1605 (11)	0.153 (3)	0.0533 (11)	0.090 (7)*
H13	0.1701 (12)	0.718 (3)	0.5233 (12)	0.099 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0454 (8)	0.0533 (8)	0.0483 (8)	−0.0005 (6)	−0.0008 (6)	0.0040 (6)
N2	0.0449 (8)	0.0652 (9)	0.0513 (8)	0.0098 (7)	−0.0043 (6)	−0.0032 (7)
C1	0.0424 (9)	0.0510 (9)	0.0474 (9)	0.0001 (7)	−0.0008 (7)	0.0054 (7)
C8	0.0459 (9)	0.0484 (9)	0.0489 (9)	0.0017 (7)	0.0051 (7)	0.0088 (7)
C3	0.0449 (9)	0.0588 (10)	0.0540 (10)	0.0024 (8)	−0.0011 (8)	0.0162 (8)
C9	0.0457 (9)	0.0503 (9)	0.0512 (10)	0.0033 (7)	0.0052 (7)	0.0168 (7)
C2	0.0468 (9)	0.0506 (9)	0.0480 (9)	−0.0056 (7)	−0.0009 (7)	0.0118 (7)
C10	0.0545 (10)	0.0578 (10)	0.0478 (10)	−0.0113 (8)	−0.0001 (8)	0.0106 (8)
C4	0.0567 (11)	0.0659 (11)	0.0607 (12)	0.0191 (9)	0.0073 (9)	0.0213 (9)
C16	0.0437 (9)	0.0549 (10)	0.0679 (12)	0.0022 (8)	−0.0008 (8)	−0.0161 (9)
C7	0.0632 (12)	0.0634 (11)	0.0524 (11)	0.0101 (9)	−0.0005 (9)	0.0026 (9)
N3	0.0647 (10)	0.0857 (12)	0.0528 (9)	0.0237 (9)	−0.0041 (7)	0.0024 (8)
C20	0.0531 (13)	0.0783 (16)	0.0912 (17)	−0.0012 (11)	0.0162 (12)	−0.0037 (13)
C5	0.0844 (15)	0.0722 (13)	0.0550 (12)	0.0320 (11)	0.0164 (11)	0.0138 (10)
C11	0.0665 (13)	0.0829 (14)	0.0526 (12)	−0.0092 (11)	−0.0073 (9)	0.0133 (10)
C15	0.0766 (14)	0.0766 (13)	0.0563 (12)	−0.0002 (11)	−0.0052 (10)	−0.0015 (10)
C6	0.0863 (15)	0.0710 (13)	0.0524 (11)	0.0241 (11)	0.0046 (10)	0.0018 (10)
C12	0.0833 (16)	0.1038 (18)	0.0586 (13)	−0.0167 (14)	−0.0144 (12)	0.0141 (13)
C18	0.0707 (13)	0.0816 (14)	0.0647 (12)	0.0302 (11)	−0.0169 (10)	−0.0101 (10)
C13	0.114 (2)	0.0989 (18)	0.0499 (13)	−0.0335 (16)	−0.0056 (13)	−0.0015 (12)
C17	0.0485 (11)	0.0761 (13)	0.0853 (15)	0.0197 (10)	−0.0127 (10)	−0.0192 (11)
C14	0.1017 (18)	0.0896 (16)	0.0651 (14)	−0.0013 (15)	0.0035 (13)	−0.0127 (12)
C19	0.117 (2)	0.149 (3)	0.0785 (16)	0.065 (2)	−0.0211 (15)	0.0087 (16)

N1—C1	1.305 (2)	C20—H20C	0.96 (3)
N1—C2	1.371 (2)	C20—H20B	0.99 (3)
N2—C16	1.364 (2)	C20—H20A	0.98 (3)
N2—N3	1.375 (2)	C5—C6	1.400 (3)
N2—C1	1.418 (2)	C5—H5	1.01 (2)
C1—C8	1.422 (2)	C11—C12	1.376 (3)
C8—C7	1.410 (2)	C11—H11	1.00 (2)
C8—C9	1.416 (2)	C15—C14	1.380 (3)
C3—C2	1.368 (2)	C15—H15	0.98 (2)
C3—C9	1.408 (2)	C6—H6	1.02 (2)
C3—H3	0.966 (18)	C12—C13	1.369 (4)
C9—C4	1.416 (2)	C12—H12	1.00 (3)
C2—C10	1.481 (2)	C18—C17	1.383 (3)
C10—C15	1.388 (3)	C18—C19	1.498 (3)
C10—C11	1.393 (3)	C13—C14	1.380 (3)
C4—C5	1.346 (3)	C13—H13	0.96 (2)
C4—H4	0.922 (18)	C17—H17	0.91 (2)
C16—C17	1.353 (3)	C14—H14	0.97 (2)
C16—C20	1.482 (3)	C19—H19A	0.9600
C7—C6	1.362 (3)	C19—H19B	0.9600
C7—H7	0.943 (19)	C19—H19C	0.9600
N3—C18	1.326 (2)
C1—N1—C2	119.00 (14)	H20C—C20—H20A	103.7 (19)
C16—N2—N3	112.22 (14)	H20B—C20—H20A	112 (2)
C16—N2—C1	128.39 (15)	C4—C5—C6	120.56 (19)
N3—N2—C1	118.85 (13)	C4—C5—H5	121.0 (11)
N1—C1—N2	115.09 (14)	C6—C5—H5	118.4 (11)
N1—C1—C8	124.98 (15)	C12—C11—C10	120.7 (2)
N2—C1—C8	119.92 (15)	C12—C11—H11	119.0 (13)
C7—C8—C9	119.62 (16)	C10—C11—H11	120.2 (13)
C7—C8—C1	124.66 (16)	C14—C15—C10	121.1 (2)
C9—C8—C1	115.72 (15)	C14—C15—H15	119.0 (12)
C2—C3—C9	120.75 (16)	C10—C15—H15	119.9 (12)
C2—C3—H3	119.8 (11)	C7—C6—C5	120.4 (2)
C9—C3—H3	119.4 (11)	C7—C6—H6	119.0 (12)
C3—C9—C4	123.67 (16)	C5—C6—H6	120.6 (12)
C3—C9—C8	118.52 (15)	C13—C12—C11	120.8 (2)
C4—C9—C8	117.80 (17)	C13—C12—H12	120.2 (14)
C3—C2—N1	120.85 (16)	C11—C12—H12	118.9 (15)
C3—C2—C10	124.57 (15)	N3—C18—C17	111.41 (18)
N1—C2—C10	114.57 (15)	N3—C18—C19	119.7 (2)
C15—C10—C11	117.79 (19)	C17—C18—C19	128.89 (19)
C15—C10—C2	120.19 (16)	C12—C13—C14	119.4 (2)
C11—C10—C2	122.00 (18)	C12—C13—H13	123.1 (14)
C5—C4—C9	121.39 (19)	C14—C13—H13	117.5 (14)
C5—C4—H4	121.1 (12)	C16—C17—C18	107.44 (18)
C9—C4—H4	117.5 (12)	C16—C17—H17	125.4 (13)
C17—C16—N2	105.19 (18)	C18—C17—H17	127.1 (13)
C17—C16—C20	131.6 (2)	C15—C14—C13	120.1 (3)
N2—C16—C20	123.14 (17)	C15—C14—H14	119.1 (13)
C6—C7—C8	120.20 (19)	C13—C14—H14	120.8 (13)
C6—C7—H7	121.4 (12)	C18—C19—H19A	109.5
C8—C7—H7	118.3 (12)	C18—C19—H19B	109.5
C18—N3—N2	103.72 (16)	H19A—C19—H19B	109.5
C16—C20—H20C	111.2 (14)	C18—C19—H19C	109.5
C16—C20—H20B	110.1 (16)	H19A—C19—H19C	109.5
H20C—C20—H20B	107 (2)	H19B—C19—H19C	109.5
C16—C20—H20A	112.9 (14)
C2—N1—C1—N2	−179.60 (14)	N3—N2—C16—C17	1.0 (2)
C2—N1—C1—C8	0.5 (2)	C1—N2—C16—C17	172.43 (17)
C16—N2—C1—N1	−43.2 (2)	N3—N2—C16—C20	177.88 (18)
N3—N2—C1—N1	127.74 (16)	C1—N2—C16—C20	−10.7 (3)
C16—N2—C1—C8	136.70 (18)	C9—C8—C7—C6	−1.0 (3)
N3—N2—C1—C8	−52.4 (2)	C1—C8—C7—C6	179.82 (18)
N1—C1—C8—C7	175.60 (16)	C16—N2—N3—C18	−0.9 (2)
N2—C1—C8—C7	−4.3 (2)	C1—N2—N3—C18	−173.20 (16)
N1—C1—C8—C9	−3.6 (2)	C9—C4—C5—C6	0.4 (3)
N2—C1—C8—C9	176.55 (14)	C15—C10—C11—C12	1.4 (3)
C2—C3—C9—C4	−178.55 (16)	C2—C10—C11—C12	−177.56 (18)
C2—C3—C9—C8	0.6 (2)	C11—C10—C15—C14	−1.5 (3)
C7—C8—C9—C3	−176.34 (15)	C2—C10—C15—C14	177.43 (19)
C1—C8—C9—C3	2.9 (2)	C8—C7—C6—C5	−1.2 (3)
C7—C8—C9—C4	2.8 (2)	C4—C5—C6—C7	1.5 (3)
C1—C8—C9—C4	−177.96 (15)	C10—C11—C12—C13	0.1 (3)
C9—C3—C2—N1	−3.8 (2)	N2—N3—C18—C17	0.4 (2)
C9—C3—C2—C10	177.19 (15)	N2—N3—C18—C19	−179.4 (2)
C1—N1—C2—C3	3.3 (2)	C11—C12—C13—C14	−1.4 (4)
C1—N1—C2—C10	−177.61 (14)	N2—C16—C17—C18	−0.7 (2)
C3—C2—C10—C15	170.61 (17)	C20—C16—C17—C18	−177.2 (2)
N1—C2—C10—C15	−8.4 (2)	N3—C18—C17—C16	0.2 (3)
C3—C2—C10—C11	−10.5 (3)	C19—C18—C17—C16	180.0 (2)
N1—C2—C10—C11	170.48 (16)	C10—C15—C14—C13	0.2 (4)
C3—C9—C4—C5	176.59 (18)	C12—C13—C14—C15	1.3 (4)
C8—C9—C4—C5	−2.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N3	0.94 (2)	2.452 (17)	3.001 (2)	117.4 (13)
C4—H4···Cg2i	0.91 (2)	2.645 (17)	3.325 (2)	131.4 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N3	0.94 (2)	2.452 (17)	3.001 (2)	117.4 (13)
C4—H4⋯Cg2i	0.91 (2)	2.645 (17)	3.325 (2)	131.4 (13)

Symmetry code: (i) . Cg2 is the centroid of the N1,C1–C3,C8,C9 ring.