1-(4-Iodo-3-phenyl-isoquinolin-1-yl)pyrrolidine-2,5-dione.

In the title compound, C(19)H(13)IN(2)O(2), the isoquinoline ring makes dihedral angles of 55.92 (3)° and 76.11 (3)° with the benzene and succinimide rings, respectively. The dihedral angle between the benzene and succinimide rings is 70.37 (3)°. In the crystal structure, the iodo atom deviates from the isoquinoline plane by 0.163 (1) Å. The crystal studied was found to be a racemic twin with a domain ratio of 0.41 (5):0.59 (5).

Related literature

For the synthesis of isoquinoline rings, see: Pandy et al. (2008 ▶). For the biological activity of isoquinolines and derivatives, see: Kletsas et al. (2004 ▶); Mach et al. (2004 ▶). For the synthesis of sterically non-hindering endocyclic ligands of the bi-isoquin­oline family and an example X-ray structure of an octa­hedral tris-chelate iron(II) complex, see: Durola et al. (2006 ▶). For red phospho­rescence of iridium complexes with isoquinolines and derivatives, see: Tsuboyama et al. (2003 ▶).

Experimental

Crystal data

C19H13IN2O2

M = 428.21

Monoclinic,

a = 8.874 (3) Å

b = 8.365 (3) Å

c = 11.292 (4) Å

β = 100.494 (3)°

V = 824.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.96 mm−1

T = 294 K

0.39 × 0.32 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.516, T max = 0.684

5068 measured reflections

2880 independent reflections

2722 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.154

S = 1.14

2880 reflections

217 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.92 e Å−3

Δρmin = −0.85 e Å−3

Absolute structure: Flack (1983 ▶), 1229 Friedel pairs

Flack parameter: 0.41 (5)

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042111/si2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042111/si2208Isup2.hkl

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

C19H13IN2O2	F(000) = 420
Mr = 428.21	Dx = 1.726 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.874 (3) Å	Cell parameters from 3132 reflections
b = 8.365 (3) Å	θ = 2.3–27.9°
c = 11.292 (4) Å	µ = 1.96 mm−1
β = 100.494 (3)°	T = 294 K
V = 824.1 (4) Å3	Block, colourless
Z = 2	0.39 × 0.32 × 0.21 mm

Bruker APEXII CCD diffractometer	2880 independent reflections
Radiation source: fine-focus sealed tube	2722 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.516, Tmax = 0.684	k = −9→10
5068 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0688P)2 + 3.9331P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
2880 reflections	Δρmax = 1.92 e Å−3
217 parameters	Δρmin = −0.85 e Å−3
1 restraint	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.41 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
I1	0.46281 (6)	0.81542 (14)	0.63285 (5)	0.0606 (3)
C19	0.9127 (11)	0.9063 (12)	0.5388 (8)	0.042 (2)
H19	0.9014	0.9804	0.4764	0.051*
C17	1.0667 (9)	0.803 (3)	0.7186 (8)	0.059 (3)
H17	1.1548	0.8082	0.7774	0.071*
C12	0.7415 (11)	0.827 (2)	−0.0459 (8)	0.050 (2)
H12A	0.8499	0.8453	−0.0437	0.060*
H12B	0.6832	0.8818	−0.1150	0.060*
C2	0.5181 (10)	0.7804 (11)	0.4622 (7)	0.039 (2)
C14	0.8040 (9)	0.794 (2)	0.5427 (7)	0.045 (3)
N1	0.7039 (8)	0.7695 (8)	0.3323 (6)	0.0352 (17)
C1	0.6664 (10)	0.7796 (9)	0.4443 (7)	0.035 (2)
C9	0.5916 (10)	0.7606 (9)	0.2384 (8)	0.0354 (19)
C3	0.3933 (10)	0.7661 (9)	0.3598 (8)	0.0339 (19)
C8	0.4349 (10)	0.7559 (10)	0.2450 (7)	0.0347 (18)
C7	0.3209 (11)	0.7417 (13)	0.1405 (9)	0.048 (2)
H7	0.3474	0.7367	0.0646	0.058*
C5	0.1268 (12)	0.7485 (14)	0.2662 (13)	0.062 (3)
H5	0.0240	0.7467	0.2732	0.074*
C4	0.2361 (11)	0.7637 (11)	0.3664 (11)	0.051 (3)
H4	0.2068	0.7728	0.4411	0.061*
C6	0.1664 (13)	0.7355 (14)	0.1537 (10)	0.052 (2)
H6	0.0901	0.7225	0.0861	0.062*
C13	0.6947 (13)	0.8815 (13)	0.0688 (9)	0.045 (2)
C15	0.8281 (12)	0.6798 (14)	0.6350 (9)	0.048 (2)
H15	0.7552	0.6007	0.6382	0.058*
C16	0.9609 (12)	0.6848 (15)	0.7222 (9)	0.051 (3)
H16	0.9777	0.6080	0.7828	0.061*
C18	1.0422 (11)	0.9091 (19)	0.6304 (10)	0.066 (4)
H18	1.1144	0.9894	0.6293	0.079*
C11	0.7047 (17)	0.6458 (13)	−0.0504 (10)	0.059 (3)
H11A	0.6281	0.6213	−0.1209	0.071*
H11B	0.7963	0.5844	−0.0544	0.071*
O1	0.7041 (11)	1.0138 (10)	0.1076 (7)	0.061 (2)
O2	0.6070 (9)	0.4793 (8)	0.0963 (7)	0.0532 (17)
N2	0.6411 (10)	0.7481 (10)	0.1276 (8)	0.0408 (17)
C10	0.6446 (12)	0.6047 (13)	0.0635 (9)	0.041 (2)

	U11	U22	U33	U12	U13	U23
I1	0.0499 (3)	0.0991 (6)	0.0354 (3)	0.0116 (5)	0.0148 (2)	−0.0016 (5)
C19	0.047 (5)	0.050 (5)	0.029 (5)	0.002 (4)	0.002 (4)	0.005 (4)
C17	0.033 (4)	0.098 (9)	0.040 (5)	0.021 (8)	−0.006 (3)	−0.006 (8)
C12	0.059 (5)	0.055 (6)	0.038 (4)	0.006 (7)	0.013 (4)	0.001 (7)
C2	0.042 (4)	0.049 (7)	0.025 (4)	−0.001 (4)	0.005 (3)	−0.008 (4)
C14	0.034 (4)	0.075 (9)	0.030 (4)	0.008 (5)	0.012 (3)	−0.008 (6)
N1	0.041 (4)	0.034 (4)	0.031 (3)	0.001 (3)	0.009 (3)	−0.002 (3)
C1	0.041 (4)	0.033 (6)	0.029 (4)	0.000 (3)	0.003 (3)	0.000 (3)
C9	0.048 (5)	0.027 (4)	0.033 (4)	−0.001 (3)	0.011 (4)	−0.003 (3)
C3	0.044 (4)	0.025 (5)	0.033 (4)	0.001 (3)	0.006 (3)	−0.001 (3)
C8	0.048 (5)	0.028 (4)	0.026 (4)	0.003 (3)	0.000 (3)	0.000 (3)
C7	0.044 (5)	0.055 (5)	0.038 (5)	−0.003 (4)	−0.011 (4)	−0.018 (4)
C5	0.035 (5)	0.054 (6)	0.095 (9)	−0.005 (4)	0.008 (5)	0.003 (6)
C4	0.042 (5)	0.048 (6)	0.062 (6)	0.001 (4)	0.010 (5)	0.005 (4)
C6	0.051 (6)	0.060 (6)	0.040 (5)	0.003 (5)	−0.003 (4)	0.007 (5)
C13	0.063 (6)	0.045 (6)	0.026 (4)	−0.010 (4)	0.004 (4)	0.010 (4)
C15	0.044 (5)	0.063 (6)	0.037 (5)	−0.002 (4)	0.006 (4)	0.000 (5)
C16	0.044 (5)	0.077 (7)	0.028 (5)	0.007 (5)	−0.002 (4)	0.008 (5)
C18	0.028 (5)	0.128 (11)	0.040 (6)	0.016 (5)	0.003 (4)	−0.010 (6)
C11	0.098 (9)	0.053 (7)	0.032 (5)	−0.006 (6)	0.022 (6)	−0.005 (4)
O1	0.098 (7)	0.050 (5)	0.030 (4)	−0.017 (4)	0.001 (4)	0.007 (3)
O2	0.080 (5)	0.035 (4)	0.047 (4)	0.000 (3)	0.017 (4)	0.002 (3)
N2	0.049 (4)	0.040 (4)	0.032 (4)	0.003 (3)	0.004 (3)	0.004 (3)
C10	0.049 (6)	0.049 (6)	0.022 (5)	0.006 (4)	−0.003 (4)	−0.012 (4)

I1—C2	2.093 (8)	C3—C8	1.414 (12)
C19—C14	1.355 (17)	C8—C7	1.412 (12)
C19—C18	1.399 (14)	C7—C6	1.407 (16)
C19—H19	0.9300	C7—H7	0.9300
C17—C18	1.32 (2)	C5—C4	1.355 (16)
C17—C16	1.37 (2)	C5—C6	1.383 (17)
C17—H17	0.9300	C5—H5	0.9300
C12—C13	1.502 (14)	C4—H4	0.9300
C12—C11	1.548 (19)	C6—H6	0.9300
C12—H12A	0.9700	C13—O1	1.188 (13)
C12—H12B	0.9700	C13—N2	1.424 (12)
C2—C1	1.368 (12)	C15—C16	1.392 (13)
C2—C3	1.453 (12)	C15—H15	0.9300
C14—C15	1.399 (17)	C16—H16	0.9300
C14—C1	1.498 (11)	C18—H18	0.9300
N1—C9	1.318 (12)	C11—C10	1.519 (15)
N1—C1	1.368 (11)	C11—H11A	0.9700
C9—N2	1.402 (12)	C11—H11B	0.9700
C9—C8	1.407 (13)	O2—C10	1.181 (13)
C3—C4	1.411 (13)	N2—C10	1.404 (13)
C14—C19—C18	118.8 (10)	C4—C5—C6	120.7 (10)
C14—C19—H19	120.6	C4—C5—H5	119.6
C18—C19—H19	120.6	C6—C5—H5	119.6
C18—C17—C16	119.2 (9)	C5—C4—C3	121.5 (11)
C18—C17—H17	120.4	C5—C4—H4	119.3
C16—C17—H17	120.4	C3—C4—H4	119.3
C13—C12—C11	103.7 (9)	C5—C6—C7	120.7 (10)
C13—C12—H12A	111.0	C5—C6—H6	119.7
C11—C12—H12A	111.0	C7—C6—H6	119.7
C13—C12—H12B	111.0	O1—C13—N2	124.4 (9)
C11—C12—H12B	111.0	O1—C13—C12	126.1 (10)
H12A—C12—H12B	109.0	N2—C13—C12	109.4 (10)
C1—C2—C3	119.8 (8)	C16—C15—C14	120.1 (10)
C1—C2—I1	122.0 (6)	C16—C15—H15	120.0
C3—C2—I1	118.1 (6)	C14—C15—H15	120.0
C19—C14—C15	119.0 (8)	C17—C16—C15	119.9 (10)
C19—C14—C1	121.2 (10)	C17—C16—H16	120.1
C15—C14—C1	119.5 (11)	C15—C16—H16	120.1
C9—N1—C1	118.2 (7)	C17—C18—C19	123.1 (13)
C2—C1—N1	122.6 (8)	C17—C18—H18	118.5
C2—C1—C14	124.5 (8)	C19—C18—H18	118.5
N1—C1—C14	112.9 (7)	C10—C11—C12	107.3 (8)
N1—C9—N2	114.1 (8)	C10—C11—H11A	110.2
N1—C9—C8	124.6 (8)	C12—C11—H11A	110.2
N2—C9—C8	121.2 (8)	C10—C11—H11B	110.2
C4—C3—C8	118.2 (9)	C12—C11—H11B	110.2
C4—C3—C2	125.3 (9)	H11A—C11—H11B	108.5
C8—C3—C2	116.5 (8)	C9—N2—C10	124.3 (8)
C9—C8—C7	121.5 (9)	C9—N2—C13	122.9 (8)
C9—C8—C3	118.2 (8)	C10—N2—C13	112.8 (8)
C7—C8—C3	120.3 (9)	O2—C10—N2	124.3 (10)
C6—C7—C8	118.6 (10)	O2—C10—C11	129.0 (9)
C6—C7—H7	120.7	N2—C10—C11	106.7 (9)
C8—C7—H7	120.7
C18—C19—C14—C15	−2.8 (16)	C6—C5—C4—C3	−0.3 (16)
C18—C19—C14—C1	−177.1 (10)	C8—C3—C4—C5	1.5 (14)
C3—C2—C1—N1	1.6 (13)	C2—C3—C4—C5	−179.4 (9)
I1—C2—C1—N1	−174.7 (6)	C4—C5—C6—C7	−1.6 (18)
C3—C2—C1—C14	−180.0 (10)	C8—C7—C6—C5	2.2 (17)
I1—C2—C1—C14	3.7 (14)	C11—C12—C13—O1	179.7 (12)
C9—N1—C1—C2	0.1 (11)	C11—C12—C13—N2	1.7 (11)
C9—N1—C1—C14	−178.5 (9)	C19—C14—C15—C16	1.0 (16)
C19—C14—C1—C2	−126.3 (10)	C1—C14—C15—C16	175.4 (10)
C15—C14—C1—C2	59.3 (15)	C18—C17—C16—C15	−1.3 (18)
C19—C14—C1—N1	52.2 (14)	C14—C15—C16—C17	1.1 (16)
C15—C14—C1—N1	−122.1 (9)	C16—C17—C18—C19	−0.6 (19)
C1—N1—C9—N2	−179.1 (7)	C14—C19—C18—C17	2.7 (17)
C1—N1—C9—C8	−2.0 (12)	C13—C12—C11—C10	−2.1 (12)
C1—C2—C3—C4	179.3 (8)	N1—C9—N2—C10	101.4 (10)
I1—C2—C3—C4	−4.2 (11)	C8—C9—N2—C10	−75.8 (12)
C1—C2—C3—C8	−1.5 (12)	N1—C9—N2—C13	−78.1 (11)
I1—C2—C3—C8	174.9 (6)	C8—C9—N2—C13	104.7 (10)
N1—C9—C8—C7	−178.2 (8)	O1—C13—N2—C9	0.8 (16)
N2—C9—C8—C7	−1.3 (13)	C12—C13—N2—C9	178.8 (8)
N1—C9—C8—C3	1.9 (12)	O1—C13—N2—C10	−178.7 (11)
N2—C9—C8—C3	178.8 (7)	C12—C13—N2—C10	−0.6 (12)
C4—C3—C8—C9	179.1 (8)	C9—N2—C10—O2	−0.3 (16)
C2—C3—C8—C9	−0.1 (11)	C13—N2—C10—O2	179.1 (10)
C4—C3—C8—C7	−0.8 (12)	C9—N2—C10—C11	179.8 (9)
C2—C3—C8—C7	−180.0 (8)	C13—N2—C10—C11	−0.8 (12)
C9—C8—C7—C6	179.1 (9)	C12—C11—C10—O2	−178.1 (11)
C3—C8—C7—C6	−1.0 (14)	C12—C11—C10—N2	1.8 (12)