N-[3-(2-Methyl-phen-yl)isoquinolin-1-yl]formamide.

The title compound, C(17)H(14)N(2)O, crystallizes as a cis formamide isomer. The isoquinoline and benzene fragments are nearly perpendicular [dihedral angle = 81.79 (18)°], whereas the formamide group is virtually coplanar with the isoquinoline unit [dihedral angle = 1.66 (15)°]. Inter-molecular N-H⋯O hydrogen bonds link mol-ecules into a centrosymmetric dimer.

Related literature

For the cytotoxic activity of aryl­isoquinolines, see: Cho et al. (2002 ▶, 2003 ▶). For the synthethic procedures relevant to this work, see: Nunno et al. (2008 ▶); Tovar & Swager (1999 ▶); Cho et al. (2002 ▶).

Experimental

Crystal data

C17H14N2O

M = 262.30

Triclinic,

a = 5.3898 (14) Å

b = 11.166 (3) Å

c = 11.899 (3) Å

α = 106.139 (3)°

β = 93.128 (3)°

γ = 103.800 (3)°

V = 662.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.36 × 0.23 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.971, T max = 0.987

4772 measured reflections

2399 independent reflections

1575 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.03

2399 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011714/gk2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011714/gk2201Isup2.hkl

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

C17H14N2O	Z = 2
Mr = 262.30	F(000) = 276
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3898 (14) Å	Cell parameters from 1222 reflections
b = 11.166 (3) Å	θ = 3.0–26.0°
c = 11.899 (3) Å	µ = 0.08 mm−1
α = 106.139 (3)°	T = 296 K
β = 93.128 (3)°	Block, colourless
γ = 103.800 (3)°	0.36 × 0.23 × 0.16 mm
V = 662.4 (3) Å3

Bruker SMART CCD area-detector diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	1575 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 3.0°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
Tmin = 0.971, Tmax = 0.987	l = −14→14
4772 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/3
2399 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.19 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 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
C1	0.2507 (3)	0.67650 (17)	0.71903 (14)	0.0446 (4)
C2	0.1010 (3)	0.74496 (17)	0.67117 (15)	0.0444 (4)
C4	−0.0799 (4)	0.8081 (2)	0.51425 (18)	0.0651 (6)
H4	−0.1015	0.8032	0.4349	0.078*
C5	−0.1976 (4)	0.8866 (2)	0.59439 (18)	0.0627 (6)
H5	−0.2959	0.9339	0.5681	0.075*
C6	−0.1697 (4)	0.8945 (2)	0.71022 (18)	0.0592 (5)
H6	−0.2504	0.9465	0.7627	0.071*
C7	−0.0188 (3)	0.82420 (18)	0.75214 (15)	0.0481 (5)
C8	0.0201 (4)	0.83123 (19)	0.87248 (16)	0.0550 (5)
H8	−0.0586	0.8820	0.9272	0.066*
C9	0.1717 (4)	0.76428 (18)	0.90878 (15)	0.0485 (5)
C10	0.5217 (4)	0.52789 (19)	0.67853 (16)	0.0551 (5)
H10	0.5431	0.5346	0.7583	0.066*
C11	0.2307 (4)	0.77304 (19)	1.03607 (15)	0.0479 (5)
C12	0.0620 (4)	0.69894 (19)	1.09041 (16)	0.0531 (5)
C13	0.1360 (4)	0.7069 (2)	1.20679 (17)	0.0623 (6)
H13	0.0261	0.6567	1.2437	0.075*
C14	0.3655 (4)	0.7863 (2)	1.26835 (18)	0.0636 (6)
H14	0.4105	0.7889	1.3457	0.076*
C15	0.5290 (4)	0.8620 (2)	1.21612 (18)	0.0662 (6)
H15	0.6831	0.9178	1.2584	0.079*
C16	0.4630 (4)	0.8548 (2)	1.09957 (17)	0.0600 (6)
H16	0.5751	0.9051	1.0635	0.072*
C17	−0.1907 (4)	0.6097 (2)	1.0258 (2)	0.0735 (6)
H17A	−0.3010	0.6596	1.0076	0.110*
H17B	−0.2710	0.5602	1.0746	0.110*
H17C	−0.1617	0.5524	0.9541	0.110*
C18	0.0666 (4)	0.7385 (2)	0.55094 (16)	0.0558 (5)
H18	0.1441	0.6866	0.4966	0.067*
N1	0.2872 (3)	0.68582 (15)	0.83158 (12)	0.0492 (4)
N2	0.3716 (3)	0.59354 (15)	0.64362 (12)	0.0517 (4)
H2	0.3469	0.5844	0.5694	0.062*
O1	0.6325 (3)	0.45974 (14)	0.61283 (11)	0.0655 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0521 (11)	0.0470 (11)	0.0386 (10)	0.0214 (9)	0.0112 (8)	0.0112 (8)
C2	0.0477 (10)	0.0478 (11)	0.0410 (10)	0.0187 (9)	0.0078 (8)	0.0134 (8)
C4	0.0777 (15)	0.0831 (16)	0.0477 (11)	0.0425 (13)	0.0049 (10)	0.0231 (11)
C5	0.0683 (13)	0.0731 (15)	0.0596 (12)	0.0387 (12)	0.0033 (10)	0.0241 (11)
C6	0.0639 (13)	0.0663 (14)	0.0569 (12)	0.0364 (11)	0.0094 (10)	0.0168 (10)
C7	0.0492 (11)	0.0519 (12)	0.0466 (10)	0.0206 (9)	0.0068 (8)	0.0142 (9)
C8	0.0668 (13)	0.0630 (13)	0.0426 (10)	0.0340 (11)	0.0147 (9)	0.0119 (9)
C9	0.0555 (11)	0.0555 (12)	0.0384 (10)	0.0238 (10)	0.0114 (8)	0.0116 (9)
C10	0.0755 (14)	0.0638 (13)	0.0380 (10)	0.0378 (12)	0.0107 (9)	0.0170 (9)
C11	0.0579 (12)	0.0535 (11)	0.0383 (9)	0.0285 (10)	0.0111 (9)	0.0104 (9)
C12	0.0595 (12)	0.0560 (12)	0.0463 (11)	0.0227 (10)	0.0070 (9)	0.0132 (9)
C13	0.0754 (15)	0.0728 (15)	0.0434 (11)	0.0228 (12)	0.0084 (10)	0.0220 (10)
C14	0.0760 (15)	0.0762 (15)	0.0417 (11)	0.0293 (13)	0.0017 (11)	0.0157 (11)
C15	0.0628 (13)	0.0766 (15)	0.0529 (12)	0.0210 (12)	−0.0034 (10)	0.0094 (11)
C16	0.0576 (13)	0.0731 (14)	0.0484 (11)	0.0181 (11)	0.0083 (10)	0.0159 (10)
C17	0.0690 (14)	0.0802 (16)	0.0671 (14)	0.0124 (13)	−0.0022 (11)	0.0239 (12)
C18	0.0651 (13)	0.0687 (14)	0.0419 (10)	0.0332 (11)	0.0089 (9)	0.0163 (10)
N1	0.0622 (10)	0.0564 (10)	0.0363 (8)	0.0285 (8)	0.0113 (7)	0.0140 (7)
N2	0.0707 (11)	0.0640 (10)	0.0326 (8)	0.0390 (9)	0.0089 (7)	0.0153 (7)
O1	0.0930 (11)	0.0775 (10)	0.0454 (7)	0.0555 (9)	0.0183 (7)	0.0194 (7)

C1—N1	1.314 (2)	C10—N2	1.334 (2)
C1—N2	1.406 (2)	C10—H10	0.9300
C1—C2	1.430 (2)	C11—C12	1.390 (3)
C2—C18	1.412 (2)	C11—C16	1.393 (3)
C2—C7	1.412 (2)	C12—C13	1.393 (3)
C4—C18	1.365 (3)	C12—C17	1.500 (3)
C4—C5	1.395 (3)	C13—C14	1.367 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.354 (3)	C14—C15	1.368 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.416 (3)	C15—C16	1.388 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.413 (2)	C16—H16	0.9300
C8—C9	1.358 (3)	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C9—N1	1.369 (2)	C17—H17C	0.9600
C9—C11	1.502 (2)	C18—H18	0.9300
C10—O1	1.218 (2)	N2—H2	0.8600
N1—C1—N2	116.00 (15)	C16—C11—C9	118.94 (17)
N1—C1—C2	124.34 (16)	C11—C12—C13	118.20 (19)
N2—C1—C2	119.66 (15)	C11—C12—C17	121.62 (17)
C18—C2—C7	118.91 (16)	C13—C12—C17	120.16 (19)
C18—C2—C1	124.80 (16)	C14—C13—C12	121.9 (2)
C7—C2—C1	116.28 (15)	C14—C13—H13	119.0
C18—C4—C5	120.80 (19)	C12—C13—H13	119.0
C18—C4—H4	119.6	C13—C14—C15	120.03 (19)
C5—C4—H4	119.6	C13—C14—H14	120.0
C6—C5—C4	120.51 (18)	C15—C14—H14	120.0
C6—C5—H5	119.7	C14—C15—C16	119.5 (2)
C4—C5—H5	119.7	C14—C15—H15	120.2
C5—C6—C7	120.56 (18)	C16—C15—H15	120.2
C5—C6—H6	119.7	C15—C16—C11	120.7 (2)
C7—C6—H6	119.7	C15—C16—H16	119.7
C2—C7—C8	118.35 (16)	C11—C16—H16	119.7
C2—C7—C6	119.00 (16)	C12—C17—H17A	109.5
C8—C7—C6	122.64 (17)	C12—C17—H17B	109.5
C9—C8—C7	120.43 (17)	H17A—C17—H17B	109.5
C9—C8—H8	119.8	C12—C17—H17C	109.5
C7—C8—H8	119.8	H17A—C17—H17C	109.5
C8—C9—N1	122.13 (16)	H17B—C17—H17C	109.5
C8—C9—C11	122.85 (16)	C4—C18—C2	120.22 (18)
N1—C9—C11	115.00 (15)	C4—C18—H18	119.9
O1—C10—N2	124.36 (17)	C2—C18—H18	119.9
O1—C10—H10	117.8	C1—N1—C9	118.43 (15)
N2—C10—H10	117.8	C10—N2—C1	124.96 (15)
C12—C11—C16	119.63 (17)	C10—N2—H2	117.5
C12—C11—C9	121.41 (17)	C1—N2—H2	117.5
N1—C1—C2—C18	178.11 (18)	C9—C11—C12—C13	176.52 (17)
N2—C1—C2—C18	−1.4 (3)	C16—C11—C12—C17	179.84 (18)
N1—C1—C2—C7	−1.8 (3)	C9—C11—C12—C17	−1.9 (3)
N2—C1—C2—C7	178.68 (16)	C11—C12—C13—C14	1.1 (3)
C18—C4—C5—C6	−0.4 (3)	C17—C12—C13—C14	179.6 (2)
C4—C5—C6—C7	0.6 (3)	C12—C13—C14—C15	0.6 (3)
C18—C2—C7—C8	−179.13 (18)	C13—C14—C15—C16	−1.7 (3)
C1—C2—C7—C8	0.8 (3)	C14—C15—C16—C11	1.0 (3)
C18—C2—C7—C6	0.1 (3)	C12—C11—C16—C15	0.7 (3)
C1—C2—C7—C6	−179.99 (17)	C9—C11—C16—C15	−177.58 (18)
C5—C6—C7—C2	−0.4 (3)	C5—C4—C18—C2	0.0 (3)
C5—C6—C7—C8	178.7 (2)	C7—C2—C18—C4	0.1 (3)
C2—C7—C8—C9	0.8 (3)	C1—C2—C18—C4	−179.81 (19)
C6—C7—C8—C9	−178.41 (19)	N2—C1—N1—C9	−179.35 (16)
C7—C8—C9—N1	−1.5 (3)	C2—C1—N1—C9	1.1 (3)
C7—C8—C9—C11	176.90 (18)	C8—C9—N1—C1	0.6 (3)
C8—C9—C11—C12	83.5 (3)	C11—C9—N1—C1	−177.95 (17)
N1—C9—C11—C12	−98.0 (2)	O1—C10—N2—C1	−177.35 (19)
C8—C9—C11—C16	−98.3 (2)	N1—C1—N2—C10	−1.6 (3)
N1—C9—C11—C16	80.3 (2)	C2—C1—N2—C10	177.92 (17)
C16—C11—C12—C13	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.10	2.940 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.10	2.940 (2)	165

Symmetry code: (i) .