The molecule of the title compound, C
9H
7NO, is nearly planar, with an r.m.s. deviation of 0.018 (7) Å. In the crystal structure, two molecules form an
R22(8) centrosymmetric dimer through N—H
O hydrogen bonds. The three-dimensional packing is additionally stabilized through weak C—H
O interactions.
Supporting information
CCDC reference: 672970
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.123
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O .. 2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O .. 2.65 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Compound (I) was synthesized in a manner similar to the procedure described by
Ferrer et al. (2002) and Parveen et al. (1999). Isocoumarin (996 mg, 6.8 mmol) in 2-methoxyethanol (30 ml) was saturated with ammonia for 3 h,
after which the mixture was boiled under reflux for 18 h. Subsequent
evaporation and recrystallization from ethylacetate yielded the title compound
(815 mg, yield 82%). Crystals suitable for X-ray diffraction have been
obtained by slow evaporation from hydrazine/water mixture (4:1) at room
temperature. IR (KBr pellet, ν, cm-1): The most intensive band in the IR
spectrum is located at 1656 cm-1 and is characteristic for νC═O
stretching mode. Skeletal stretching of aromatic ring, νC≐C, are
detected at 1605, 1549, 1475, 1346 and 1230 cm-1. The νC—H of the
phenyl group appears at 551, 669 and 797 cm-1(m), and in the
2855–3160 cm-1 (w) region. The weak broad band at 3290 cm-1 is associated
with the N—H group.
All H atoms were placed in idealized positions (C—H = 0.93 and N—H = 0.86 Å) and were constrained to ride on their parent atoms, with Uiso(H)
= 1.2Ueq(C or N).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
Isoquinolin-1(2
H)-one
top
Crystal data top
C9H7NO | F(000) = 304 |
Mr = 145.16 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/n | Melting point: not measured K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6138 (17) Å | Cell parameters from 22 reflections |
b = 5.2965 (9) Å | θ = 18.0–19.2° |
c = 12.2946 (9) Å | µ = 0.09 mm−1 |
β = 111.745 (9)° | T = 290 K |
V = 702.46 (17) Å3 | Prism, pale orange |
Z = 4 | 0.36 × 0.36 × 0.34 mm |
Data collection top
Enraf–Nonius CAD4 diffractometer | Rint = 0.044 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.1° |
Graphite monochromator | h = 0→15 |
ω/2θ scans | k = −6→6 |
3292 measured reflections | l = −16→15 |
1678 independent reflections | 3 standard reflections every 120 min |
1053 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0424P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1678 reflections | Δρmax = 0.20 e Å−3 |
101 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (5) |
Crystal data top
C9H7NO | V = 702.46 (17) Å3 |
Mr = 145.16 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.6138 (17) Å | µ = 0.09 mm−1 |
b = 5.2965 (9) Å | T = 290 K |
c = 12.2946 (9) Å | 0.36 × 0.36 × 0.34 mm |
β = 111.745 (9)° | |
Data collection top
Enraf–Nonius CAD4 diffractometer | Rint = 0.044 |
3292 measured reflections | 3 standard reflections every 120 min |
1678 independent reflections | intensity decay: none |
1053 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.20 e Å−3 |
1678 reflections | Δρmin = −0.16 e Å−3 |
101 parameters | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.67389 (14) | 0.5067 (3) | 0.44839 (13) | 0.0362 (4) | |
C2 | 0.79688 (14) | 0.4736 (3) | 0.52641 (13) | 0.0418 (4) | |
C3 | 0.86794 (17) | 0.2858 (4) | 0.50006 (17) | 0.0534 (5) | |
H3 | 0.9499 | 0.2615 | 0.5497 | 0.064* | |
C4 | 0.81862 (18) | 0.1389 (4) | 0.40290 (17) | 0.0581 (5) | |
H4 | 0.8675 | 0.0161 | 0.3870 | 0.070* | |
C5 | 0.69666 (18) | 0.1697 (4) | 0.32727 (16) | 0.0525 (5) | |
H5 | 0.6636 | 0.0666 | 0.2617 | 0.063* | |
C6 | 0.62517 (15) | 0.3528 (3) | 0.34971 (14) | 0.0447 (4) | |
H6 | 0.5435 | 0.3747 | 0.2988 | 0.054* | |
C7 | 0.59723 (14) | 0.7040 (3) | 0.46979 (13) | 0.0380 (4) | |
C8 | 0.77064 (15) | 0.8060 (3) | 0.64655 (14) | 0.0457 (4) | |
H8 | 0.8011 | 0.9065 | 0.7132 | 0.055* | |
C9 | 0.84330 (15) | 0.6297 (4) | 0.62860 (15) | 0.0485 (5) | |
H9 | 0.9238 | 0.6080 | 0.6821 | 0.058* | |
N | 0.65169 (12) | 0.8423 (3) | 0.56868 (11) | 0.0428 (4) | |
H1N | 0.6088 | 0.9604 | 0.5835 | 0.051* | |
O | 0.48896 (10) | 0.7471 (2) | 0.40287 (10) | 0.0481 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0357 (8) | 0.0373 (8) | 0.0359 (7) | 0.0028 (7) | 0.0135 (6) | 0.0052 (7) |
C2 | 0.0382 (9) | 0.0438 (10) | 0.0421 (9) | 0.0064 (7) | 0.0135 (7) | 0.0079 (7) |
C3 | 0.0428 (10) | 0.0582 (12) | 0.0558 (10) | 0.0179 (9) | 0.0142 (8) | 0.0076 (9) |
C4 | 0.0640 (12) | 0.0518 (11) | 0.0627 (12) | 0.0208 (9) | 0.0282 (10) | 0.0026 (9) |
C5 | 0.0618 (11) | 0.0486 (10) | 0.0492 (10) | 0.0042 (9) | 0.0229 (9) | −0.0052 (8) |
C6 | 0.0429 (9) | 0.0477 (10) | 0.0411 (9) | 0.0019 (8) | 0.0128 (7) | 0.0018 (7) |
C7 | 0.0357 (8) | 0.0403 (9) | 0.0357 (8) | 0.0020 (7) | 0.0108 (7) | 0.0032 (7) |
C8 | 0.0413 (9) | 0.0498 (10) | 0.0376 (8) | 0.0020 (8) | 0.0049 (7) | −0.0031 (7) |
C9 | 0.0356 (9) | 0.0563 (11) | 0.0449 (9) | 0.0069 (8) | 0.0048 (7) | 0.0035 (8) |
N | 0.0379 (7) | 0.0452 (8) | 0.0408 (7) | 0.0091 (6) | 0.0094 (6) | −0.0024 (6) |
O | 0.0344 (6) | 0.0548 (8) | 0.0457 (6) | 0.0113 (5) | 0.0039 (5) | −0.0026 (5) |
Geometric parameters (Å, º) top
C1—C6 | 1.396 (2) | C5—H5 | 0.9300 |
C1—C2 | 1.406 (2) | C6—H6 | 0.9300 |
C1—C7 | 1.458 (2) | C7—O | 1.2423 (18) |
C2—C3 | 1.405 (2) | C7—N | 1.358 (2) |
C2—C9 | 1.432 (2) | C8—C9 | 1.331 (2) |
C3—C4 | 1.362 (3) | C8—N | 1.3718 (19) |
C3—H3 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.386 (3) | C9—H9 | 0.9300 |
C4—H4 | 0.9300 | N—H1N | 0.8600 |
C5—C6 | 1.370 (2) | | |
| | | |
C6—C1—C2 | 120.15 (15) | C5—C6—C1 | 120.53 (16) |
C6—C1—C7 | 119.82 (14) | C5—C6—H6 | 119.7 |
C2—C1—C7 | 120.02 (14) | C1—C6—H6 | 119.7 |
C3—C2—C1 | 117.80 (15) | O—C7—N | 121.01 (14) |
C3—C2—C9 | 123.28 (15) | O—C7—C1 | 123.22 (14) |
C1—C2—C9 | 118.92 (15) | N—C7—C1 | 115.77 (13) |
C4—C3—C2 | 120.99 (17) | C9—C8—N | 121.28 (15) |
C4—C3—H3 | 119.5 | C9—C8—H8 | 119.4 |
C2—C3—H3 | 119.5 | N—C8—H8 | 119.4 |
C3—C4—C5 | 120.97 (17) | C8—C9—C2 | 119.67 (15) |
C3—C4—H4 | 119.5 | C8—C9—H9 | 120.2 |
C5—C4—H4 | 119.5 | C2—C9—H9 | 120.2 |
C6—C5—C4 | 119.54 (17) | C7—N—C8 | 124.31 (14) |
C6—C5—H5 | 120.2 | C7—N—H1N | 117.8 |
C4—C5—H5 | 120.2 | C8—N—H1N | 117.8 |
| | | |
C6—C1—C2—C3 | 1.2 (2) | C6—C1—C7—O | −1.1 (2) |
C7—C1—C2—C3 | −178.18 (14) | C2—C1—C7—O | 178.23 (15) |
C6—C1—C2—C9 | −178.33 (16) | C6—C1—C7—N | 179.14 (14) |
C7—C1—C2—C9 | 2.3 (2) | C2—C1—C7—N | −1.5 (2) |
C1—C2—C3—C4 | −0.8 (3) | N—C8—C9—C2 | −0.2 (3) |
C9—C2—C3—C4 | 178.67 (18) | C3—C2—C9—C8 | 179.07 (17) |
C2—C3—C4—C5 | −0.2 (3) | C1—C2—C9—C8 | −1.4 (3) |
C3—C4—C5—C6 | 0.9 (3) | O—C7—N—C8 | −179.94 (15) |
C4—C5—C6—C1 | −0.5 (3) | C1—C7—N—C8 | −0.2 (2) |
C2—C1—C6—C5 | −0.5 (2) | C9—C8—N—C7 | 1.1 (3) |
C7—C1—C6—C5 | 178.83 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···Oi | 0.86 | 1.96 | 2.818 (2) | 172 |
C8—H8···Oii | 0.93 | 2.66 | 3.243 (2) | 121 |
C9—H9···Oii | 0.93 | 2.65 | 3.230 (2) | 121 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C9H7NO |
Mr | 145.16 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 290 |
a, b, c (Å) | 11.6138 (17), 5.2965 (9), 12.2946 (9) |
β (°) | 111.745 (9) |
V (Å3) | 702.46 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.36 × 0.36 × 0.34 |
|
Data collection |
Diffractometer | Enraf–Nonius CAD4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3292, 1678, 1053 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.660 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.123, 1.01 |
No. of reflections | 1678 |
No. of parameters | 101 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.16 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···Oi | 0.86 | 1.96 | 2.818 (2) | 172 |
C8—H8···Oii | 0.93 | 2.66 | 3.243 (2) | 121 |
C9—H9···Oii | 0.93 | 2.65 | 3.230 (2) | 121 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1/2, −y+3/2, z+1/2. |
Isoquinolines are important from both technological and applied points of view as a part of a significant class of compounds with a variety of pharmacological applications in anticancer, retroviral infections, rheumatoid arthritis and diabets treatment (Jayaraman et al., 2000; Zhang et al., 1997; Bernan et al., 1994; Koleva et al., 1998).
As part of our research on isoquinoline derivatives the structures of (3RS,4RS)-3-(2-furyl)-2-phenethyl-4-(pyrrolidin-1-ylcarbonyl)-3,4- dihydroisoquinolin-1(2H)-one (Petrova et al., 2005) and 1,2,3,4-tetrahydroisoquinolinium hydrogensquarate (Kolev et al., 2007) were reported. The title compound,(I), was investigated in order to provide relevant information on the changes observed upon substitution.
In the asymmetric unit of (I), only one independent molecule is present (Fig. 1). The fused ring system is nearly planar with an r.m.s. deviation of 0.018 (7) Å. The molecules are coupled through bicyclic N—H1···Oi [symmetry code (i): -x + 1, -y + 2, -z + 1] hydrogen bonds and build R22(8) dimers (Fig. 2) (Bernstein et al., 1995). The three-dimensional packing is stabilized through weak C8—H8···Oii and C9—H9···Oii interactions [symmetry code (ii): 1/2 + x, 3/2 - y, 1/2 + z].