3-Phenyl­isoquinolin-1(2H)-one

Abstract

The title compound, C₁₅H₁₁NO, consists of a planar isoquinolinone group to which a phenyl ring is attached in a twisted fashion [dihedral angle = 39.44 (4)°]. The crystal packing is dominated by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds which define centrosymmetric dimeric entitities.

Related literature

For general background and related crystal structures, see: Cho et al. (2002 ▶) and references therein. For new chemotherapeutic agents for the treatment of cancer derived from natural compounds, see: Mackay et al. (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

• C₁₅H₁₁NO

• M _r = 221.25

• Triclinic,

• a = 3.8692 (5) Å

• b = 12.0171 (16) Å

• c = 12.3209 (16) Å

• α = 106.652 (2)°

• β = 94.137 (2)°

• γ = 90.579 (2)°

• V = 547.14 (12) ų

• Z = 2

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 290 (2) K

• 0.21 × 0.15 × 0.08 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.993

• 5473 measured reflections

• 2001 independent reflections

• 1545 reflections with I > 2σ(I)

• R _int = 0.016

Refinement

• R[F ² > 2σ(F ²)] = 0.039

• wR(F ²) = 0.106

• S = 1.06

• 2001 reflections

• 158 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −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: ORTEP-3 (Farrugia, 1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.896 (16)	1.945 (16)	2.8373 (15)	174.0 (15)
C11—H11⋯O1ii	0.93	2.59	3.4449 (19)	152

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

New chemotherapeutic agents for a treatment of cancer from natural compounds have been developed over the last decade (Mackay et al., 1997). Most of the 3-arylisoquinoline derivatives exhibited potent cytotoxicities against five different human tumor cell lines. These potent antitumor activity is studied by molecular modeling to correlate structure-activity relationships (Cho et al., 2002 and references therein).

In the title compound C₁₅H₁₁NO (Fig. 1) the phenyl ring attached to the isoquinolinone moiety at C2 is twisted, forming a dihedral angle of 39.44 (4)°. Bond lengths and angles are within normal ranges (Allen et al., 1987). The C₁₅H₁₁NO monomers are linked via N—H···O and C—H···O hydrogen bonds to form dimers across the inversion center located at (1/2, 1/2, 0) (Fig. 2) and giving raise to two R¹₂(7) and one R²₂(14) graph-set motifs respectively (Bernstein et al., 1995).

Experimental

A solution of 3-pheylisocoumarin in THF was treated with ammonia and stirred overnight under reflux conditions; the solvent was concentrated to give the solid which was further purified by column chromatography. The material was recrystalized from Dichloromethane.

Refinement

All the H atoms in (I) were positioned geometrically and refined using a riding model with C—H = 0.93Å and U_iso(H) = 1.2U_eq(C) for aromatic H atoms. The H atom of N was located from difference fourier map and refined isotropically resulting in N—H abond length of 0.895 (17) Å.

Figures

Fig. 1.

ORTEP diagram of molecule (I) with 50% probability displacement ellipsoids.

Fig. 2.

The crystal packing diagram of (I).The dotted lines indicate intermolecular interactions. H atoms not involved in H-bonding have been omitted for clarity.

Crystal data

C15H11NO	Z = 2
Mr = 221.25	F(000) = 232
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8692 (5) Å	Cell parameters from 956 reflections
b = 12.0171 (16) Å	θ = 2.0–24.7°
c = 12.3209 (16) Å	µ = 0.09 mm−1
α = 106.652 (2)°	T = 290 K
β = 94.137 (2)°	Plate, brown
γ = 90.579 (2)°	0.21 × 0.15 × 0.08 mm
V = 547.14 (12) Å3

Data collection

Bruker SMART CCD area-detector diffractometer	2001 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.938, Tmax = 0.993	k = −14→14
5473 measured reflections	l = −14→14

Refinement

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.0314P] where P = (Fo2 + 2Fc2)/3
2001 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3290 (3)	0.49798 (9)	0.14029 (9)	0.0377 (3)
H1N	0.425 (4)	0.4508 (14)	0.0808 (14)	0.053 (4)*
O1	0.3406 (3)	0.63724 (8)	0.04974 (8)	0.0494 (3)
C1	0.2740 (3)	0.60824 (11)	0.13505 (11)	0.0370 (3)
C2	0.2647 (3)	0.45724 (11)	0.23136 (11)	0.0355 (3)
C3	0.1426 (4)	0.53085 (11)	0.32449 (11)	0.0404 (3)
H3	0.1027	0.5045	0.3866	0.048*
C4	−0.0576 (4)	0.72807 (13)	0.42310 (12)	0.0475 (4)
H4	−0.1023	0.7044	0.4864	0.057*
C5	−0.1204 (4)	0.83970 (13)	0.42281 (13)	0.0539 (4)
H5	−0.2067	0.8912	0.4859	0.065*
C6	−0.0564 (4)	0.87701 (13)	0.32897 (14)	0.0540 (4)
H6	−0.0988	0.9533	0.3298	0.065*
C7	0.0688 (4)	0.80168 (12)	0.23554 (12)	0.0461 (4)
H7	0.1092	0.8266	0.1726	0.055*
C8	0.1361 (3)	0.68737 (11)	0.23437 (11)	0.0372 (3)
C9	0.0743 (3)	0.64835 (12)	0.32866 (11)	0.0377 (3)
C10	0.3263 (3)	0.33257 (11)	0.21691 (11)	0.0371 (3)
C11	0.2399 (4)	0.25028 (12)	0.11318 (12)	0.0434 (4)
H11	0.1454	0.2735	0.0519	0.052*
C12	0.2941 (4)	0.13396 (13)	0.10093 (14)	0.0526 (4)
H12	0.2356	0.0792	0.0313	0.063*
C13	0.4338 (4)	0.09853 (13)	0.19090 (15)	0.0558 (4)
H13	0.4695	0.0201	0.1821	0.067*
C14	0.5206 (4)	0.17909 (13)	0.29387 (14)	0.0527 (4)
H14	0.6149	0.1551	0.3547	0.063*
C15	0.4681 (4)	0.29547 (12)	0.30712 (12)	0.0442 (4)
H15	0.5279	0.3496	0.3770	0.053*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.0459 (7)	0.0342 (6)	0.0338 (6)	0.0047 (5)	0.0075 (5)	0.0098 (5)
O1	0.0698 (7)	0.0432 (6)	0.0407 (6)	0.0101 (5)	0.0135 (5)	0.0181 (5)
C1	0.0399 (8)	0.0366 (7)	0.0351 (7)	0.0009 (6)	0.0006 (6)	0.0118 (6)
C2	0.0352 (7)	0.0375 (7)	0.0346 (7)	−0.0010 (5)	0.0016 (5)	0.0120 (6)
C3	0.0441 (8)	0.0436 (8)	0.0356 (7)	−0.0006 (6)	0.0054 (6)	0.0144 (6)
C4	0.0477 (9)	0.0507 (9)	0.0400 (8)	0.0004 (7)	0.0065 (6)	0.0059 (7)
C5	0.0530 (9)	0.0483 (9)	0.0493 (9)	0.0076 (7)	0.0040 (7)	−0.0036 (7)
C6	0.0593 (10)	0.0376 (8)	0.0587 (10)	0.0082 (7)	−0.0026 (8)	0.0053 (7)
C7	0.0518 (9)	0.0393 (8)	0.0458 (8)	0.0026 (6)	−0.0010 (7)	0.0111 (6)
C8	0.0352 (7)	0.0367 (7)	0.0375 (7)	0.0002 (6)	−0.0020 (5)	0.0082 (6)
C9	0.0341 (7)	0.0403 (8)	0.0356 (7)	−0.0015 (6)	0.0015 (5)	0.0062 (6)
C10	0.0345 (7)	0.0377 (7)	0.0417 (8)	0.0003 (6)	0.0068 (6)	0.0148 (6)
C11	0.0493 (9)	0.0375 (8)	0.0444 (8)	0.0002 (6)	0.0017 (6)	0.0137 (6)
C12	0.0591 (10)	0.0383 (8)	0.0568 (10)	−0.0021 (7)	0.0041 (7)	0.0082 (7)
C13	0.0591 (10)	0.0386 (8)	0.0752 (11)	0.0049 (7)	0.0100 (8)	0.0240 (8)
C14	0.0554 (10)	0.0525 (9)	0.0590 (10)	0.0073 (7)	0.0046 (7)	0.0301 (8)
C15	0.0476 (8)	0.0455 (8)	0.0421 (8)	0.0018 (6)	0.0028 (6)	0.0170 (6)

Geometric parameters (Å, °)

N1—C1	1.3631 (17)	C6—H6	0.9300
N1—C2	1.3831 (16)	C7—C8	1.3970 (19)
N1—H1N	0.895 (17)	C7—H7	0.9300
O1—C1	1.2408 (15)	C8—C9	1.4060 (18)
C1—C8	1.4574 (19)	C10—C11	1.3894 (19)
C2—C3	1.3518 (18)	C10—C15	1.3914 (19)
C2—C10	1.4811 (18)	C11—C12	1.382 (2)
C3—C9	1.4263 (19)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.375 (2)
C4—C5	1.367 (2)	C12—H12	0.9300
C4—C9	1.410 (2)	C13—C14	1.374 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.391 (2)	C14—C15	1.380 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.368 (2)	C15—H15	0.9300
C1—N1—C2	125.14 (12)	C7—C8—C9	120.48 (13)
C1—N1—H1N	115.8 (10)	C7—C8—C1	119.76 (12)
C2—N1—H1N	119.0 (10)	C9—C8—C1	119.76 (12)
O1—C1—N1	120.67 (12)	C8—C9—C4	117.81 (13)
O1—C1—C8	123.27 (12)	C8—C9—C3	119.16 (12)
N1—C1—C8	116.06 (11)	C4—C9—C3	123.03 (13)
C3—C2—N1	119.03 (12)	C11—C10—C15	118.75 (13)
C3—C2—C10	124.69 (12)	C11—C10—C2	120.53 (12)
N1—C2—C10	116.25 (11)	C15—C10—C2	120.72 (12)
C2—C3—C9	120.84 (12)	C12—C11—C10	120.12 (13)
C2—C3—H3	119.6	C12—C11—H11	119.9
C9—C3—H3	119.6	C10—C11—H11	119.9
C5—C4—C9	120.84 (14)	C13—C12—C11	120.49 (15)
C5—C4—H4	119.6	C13—C12—H12	119.8
C9—C4—H4	119.6	C11—C12—H12	119.8
C4—C5—C6	120.60 (14)	C14—C13—C12	119.93 (14)
C4—C5—H5	119.7	C14—C13—H13	120.0
C6—C5—H5	119.7	C12—C13—H13	120.0
C7—C6—C5	120.09 (14)	C13—C14—C15	120.12 (14)
C7—C6—H6	120.0	C13—C14—H14	119.9
C5—C6—H6	120.0	C15—C14—H14	119.9
C6—C7—C8	120.18 (14)	C14—C15—C10	120.59 (14)
C6—C7—H7	119.9	C14—C15—H15	119.7
C8—C7—H7	119.9	C10—C15—H15	119.7
C2—N1—C1—O1	179.73 (12)	C1—C8—C9—C3	−1.05 (19)
C2—N1—C1—C8	−0.11 (19)	C5—C4—C9—C8	−0.4 (2)
C1—N1—C2—C3	−1.0 (2)	C5—C4—C9—C3	−179.69 (13)
C1—N1—C2—C10	177.01 (11)	C2—C3—C9—C8	−0.1 (2)
N1—C2—C3—C9	1.15 (19)	C2—C3—C9—C4	179.11 (13)
C10—C2—C3—C9	−176.74 (12)	C3—C2—C10—C11	139.32 (15)
C9—C4—C5—C6	0.2 (2)	N1—C2—C10—C11	−38.62 (18)
C4—C5—C6—C7	0.3 (2)	C3—C2—C10—C15	−39.97 (19)
C5—C6—C7—C8	−0.6 (2)	N1—C2—C10—C15	142.09 (13)
C6—C7—C8—C9	0.4 (2)	C15—C10—C11—C12	0.2 (2)
C6—C7—C8—C1	−179.14 (13)	C2—C10—C11—C12	−179.14 (13)
O1—C1—C8—C7	0.8 (2)	C10—C11—C12—C13	0.0 (2)
N1—C1—C8—C7	−179.33 (11)	C11—C12—C13—C14	0.0 (2)
O1—C1—C8—C9	−178.69 (12)	C12—C13—C14—C15	−0.1 (2)
N1—C1—C8—C9	1.15 (18)	C13—C14—C15—C10	0.2 (2)
C7—C8—C9—C4	0.2 (2)	C11—C10—C15—C14	−0.2 (2)
C1—C8—C9—C4	179.67 (12)	C2—C10—C15—C14	179.07 (13)
C7—C8—C9—C3	179.44 (12)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.896 (16)	1.945 (16)	2.8373 (15)	174.0 (15)
C11—H11···O1ii	0.93	2.59	3.4449 (19)	152

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.