Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027729/wn2150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027729/wn2150Isup2.hkl |
CCDC reference: 654917
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.133
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C19 .. 6.68 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Cooney (1983); Hendrickson & Rodriguez (1983); Pływaczyk et al. (1984); Ruchirawat et al. (1977); Tykarska et al. (1985).
The title compound, (±)-2-benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, was obtained by reaction of 8-ethyl-isoquinoline with benzoyl chloride and trimethylsilyl cyanide in anhydrous dichloromethane (Ruchirawat et al., 1977).
8-Ethylisoquinoline was prepared from 2-ethylbenzaldehyde by the Hendrickson modification of the Pomeranz-Fritsch synthesis (Hendrickson & Rodriguez, 1983).
Crystals were obtained by slow evaporation of a methanol solution at room temperature.
H6, attached to C6, was located in a difference map and refined freely. All other H atoms were placed at idealized positions and allowed to ride on their parent atoms, with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene groups, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic carbons, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl group.
Reissert compounds are of major synthetic interest as reagents for different synthetic pathways, such as alkylation, condensation with aldehydes and ketones, rearrangements and conjugate additions (Cooney, 1983).
2-Benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, is a Reissert compound. As expected, bond lengths and angles are similar to those observed in the analogue with no ethyl group at C4 (Tykarska et al., 1985). All bond lengths of the nitrogen-containing six-membered ring of the isoquinoline group are different, ranging from 1.330 (2) Å to 1.515 (2) Å and are significantly different from those observed in the tetrahydrogenated non-ethylated derivative (Pływaczyk et al., 1984). Bond angles at N1, C5, C7, C8, C9 (ranging from 116.3 (1)° to 121.1 (1)°) are typical for sp2 hybridization. The N1—C6—C5 angle is significantly smaller (111.7 (1)°), approaching, as expected, the classical value for an sp3 hybridization. The heterocyclic ring molecule exhibits a 1,3-diplanar conformation.
The phenyl ring is connected to the isoquinoline unit via an amide bond that adopts an anti conformation with respect to the adjacent C7—N1 bond. Coplanarity of the aromatic system of the isoquinoline moiety and the amide group allows maximum conjugation. In contrast, the amide group and the phenyl ring are not conjugated, with an N1—C10—C11—C12 torsion angle of 140.6 (1)°. A similar conformation is observed for the unsubstituted analogue, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline.
Interestingly, the ethyl group is almost perpendicular to the dihydroisoquinoline system (C3—C4—C17—C18 = -105.7 (2)°) and points in the same direction as the cyano group.
For related literature, see: Cooney (1983); Hendrickson & Rodriguez (1983); Pływaczyk et al. (1984); Ruchirawat et al. (1977); Tykarska et al. (1985).
Data collection: locally modified CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Fig. 1. The molecular structure of the title compound, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. |
C19H16N2O | V = 761.0 (2) Å3 |
Mr = 288.34 | Z = 2 |
Triclinic, P1 | F(000) = 304 |
Hall symbol: -P 1 | Least Squares Treatment of 25 SET4 setting angles. |
a = 7.996 (1) Å | Dx = 1.258 Mg m−3 |
b = 8.948 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
c = 11.297 (2) Å | µ = 0.62 mm−1 |
α = 108.51 (2)° | T = 293 K |
β = 94.86 (1)° | Prism, colourless |
γ = 93.04 (1)° | 0.25 × 0.19 × 0.15 mm |
Enraf–Nonius CAD-4 diffractometer | 3129 independent reflections |
Radiation source: sealed tube | 2863 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 18.4 pixels mm-1 | θmax = 75.1°, θmin = 4.2° |
profile data from θ/2θ scans | h = 0→10 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −11→11 |
Tmin = 0.870, Tmax = 0.912 | l = −14→14 |
3363 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.073P)2 + 0.146P] where P = (Fo2 + 2Fc2)/3 |
3129 reflections | (Δ/σ)max = 0.002 |
204 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C19H16N2O | γ = 93.04 (1)° |
Mr = 288.34 | V = 761.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.996 (1) Å | Cu Kα radiation |
b = 8.948 (1) Å | µ = 0.62 mm−1 |
c = 11.297 (2) Å | T = 293 K |
α = 108.51 (2)° | 0.25 × 0.19 × 0.15 mm |
β = 94.86 (1)° |
Enraf–Nonius CAD-4 diffractometer | 3129 independent reflections |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | 2863 reflections with I > 2σ(I) |
Tmin = 0.870, Tmax = 0.912 | Rint = 0.016 |
3363 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.16 e Å−3 |
3129 reflections | Δρmin = −0.27 e Å−3 |
204 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.90833 (12) | 0.53709 (13) | 0.34650 (11) | 0.0621 (3) | |
N1 | 0.62678 (12) | 0.54197 (12) | 0.32412 (9) | 0.0387 (3) | |
N2 | 0.6167 (2) | 0.15692 (17) | 0.30988 (14) | 0.0725 (5) | |
C1 | 0.16240 (19) | 0.39167 (19) | 0.10521 (15) | 0.0571 (5) | |
C2 | 0.1597 (2) | 0.3137 (2) | −0.02105 (17) | 0.0689 (6) | |
C3 | 0.3059 (2) | 0.2683 (2) | −0.07305 (14) | 0.0633 (5) | |
C4 | 0.46169 (19) | 0.29521 (15) | 0.00046 (12) | 0.0480 (4) | |
C5 | 0.46170 (16) | 0.37120 (14) | 0.12923 (11) | 0.0390 (3) | |
C6 | 0.61905 (16) | 0.39340 (14) | 0.21979 (11) | 0.0399 (3) | |
C7 | 0.47592 (15) | 0.57954 (14) | 0.37858 (12) | 0.0394 (3) | |
C8 | 0.32744 (16) | 0.51787 (15) | 0.31459 (12) | 0.0426 (4) | |
C9 | 0.31451 (16) | 0.42280 (15) | 0.18231 (12) | 0.0421 (4) | |
C10 | 0.78571 (15) | 0.60681 (15) | 0.38120 (12) | 0.0416 (4) | |
C11 | 0.80173 (15) | 0.76349 (14) | 0.48144 (11) | 0.0390 (3) | |
C12 | 0.91843 (17) | 0.78653 (17) | 0.58549 (14) | 0.0515 (4) | |
C13 | 0.9493 (2) | 0.9350 (2) | 0.67430 (15) | 0.0610 (5) | |
C14 | 0.8673 (2) | 1.06002 (18) | 0.65893 (15) | 0.0576 (5) | |
C15 | 0.7526 (2) | 1.03744 (17) | 0.55620 (14) | 0.0546 (5) | |
C16 | 0.71761 (17) | 0.88929 (16) | 0.46778 (13) | 0.0460 (4) | |
C17 | 0.6199 (2) | 0.24568 (18) | −0.05984 (14) | 0.0588 (5) | |
C18 | 0.6905 (2) | 0.1002 (2) | −0.04024 (18) | 0.0698 (6) | |
C19 | 0.62085 (18) | 0.25958 (16) | 0.27124 (12) | 0.0480 (4) | |
H1 | 0.06320 | 0.42360 | 0.13920 | 0.0680* | |
H2 | 0.05790 | 0.29130 | −0.07200 | 0.0830* | |
H3 | 0.30130 | 0.21850 | −0.15920 | 0.0760* | |
H6 | 0.719 (2) | 0.3929 (18) | 0.1796 (15) | 0.048 (4)* | |
H7 | 0.48020 | 0.64840 | 0.46030 | 0.0470* | |
H8 | 0.23020 | 0.53570 | 0.35490 | 0.0510* | |
H12 | 0.97530 | 0.70250 | 0.59520 | 0.0620* | |
H13 | 1.02580 | 0.95050 | 0.74470 | 0.0730* | |
H14 | 0.88970 | 1.16000 | 0.71830 | 0.0690* | |
H15 | 0.69800 | 1.12250 | 0.54600 | 0.0650* | |
H16 | 0.63780 | 0.87410 | 0.39930 | 0.0550* | |
H17A | 0.70600 | 0.33330 | −0.02750 | 0.0710* | |
H17B | 0.59700 | 0.22620 | −0.14940 | 0.0710* | |
H18A | 0.71600 | 0.11820 | 0.04800 | 0.1050* | |
H18B | 0.79130 | 0.07950 | −0.08100 | 0.1050* | |
H18C | 0.60870 | 0.01100 | −0.07530 | 0.1050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (5) | 0.0583 (6) | 0.0750 (7) | 0.0123 (4) | 0.0035 (5) | −0.0035 (5) |
N1 | 0.0335 (5) | 0.0385 (5) | 0.0388 (5) | 0.0050 (4) | 0.0048 (4) | 0.0046 (4) |
N2 | 0.0948 (11) | 0.0607 (8) | 0.0668 (9) | 0.0215 (8) | −0.0015 (8) | 0.0277 (7) |
C1 | 0.0426 (7) | 0.0596 (9) | 0.0638 (9) | 0.0006 (6) | −0.0058 (6) | 0.0162 (7) |
C2 | 0.0592 (10) | 0.0764 (11) | 0.0620 (10) | −0.0044 (8) | −0.0192 (8) | 0.0179 (8) |
C3 | 0.0801 (11) | 0.0634 (9) | 0.0387 (7) | −0.0084 (8) | −0.0084 (7) | 0.0116 (6) |
C4 | 0.0628 (9) | 0.0406 (6) | 0.0394 (6) | −0.0031 (6) | 0.0047 (6) | 0.0126 (5) |
C5 | 0.0436 (6) | 0.0347 (6) | 0.0384 (6) | 0.0000 (5) | 0.0026 (5) | 0.0125 (5) |
C6 | 0.0373 (6) | 0.0392 (6) | 0.0394 (6) | 0.0067 (5) | 0.0074 (5) | 0.0062 (5) |
C7 | 0.0378 (6) | 0.0392 (6) | 0.0396 (6) | 0.0078 (5) | 0.0086 (5) | 0.0086 (5) |
C8 | 0.0347 (6) | 0.0441 (7) | 0.0487 (7) | 0.0059 (5) | 0.0089 (5) | 0.0129 (5) |
C9 | 0.0396 (6) | 0.0395 (6) | 0.0468 (7) | 0.0003 (5) | −0.0001 (5) | 0.0151 (5) |
C10 | 0.0339 (6) | 0.0416 (6) | 0.0467 (7) | 0.0068 (5) | 0.0041 (5) | 0.0102 (5) |
C11 | 0.0326 (6) | 0.0402 (6) | 0.0423 (6) | 0.0016 (5) | 0.0044 (5) | 0.0107 (5) |
C12 | 0.0424 (7) | 0.0521 (8) | 0.0562 (8) | 0.0076 (6) | −0.0046 (6) | 0.0140 (6) |
C13 | 0.0528 (8) | 0.0674 (10) | 0.0496 (8) | 0.0018 (7) | −0.0100 (6) | 0.0051 (7) |
C14 | 0.0619 (9) | 0.0471 (7) | 0.0512 (8) | −0.0019 (6) | 0.0060 (7) | −0.0007 (6) |
C15 | 0.0657 (9) | 0.0417 (7) | 0.0552 (8) | 0.0108 (6) | 0.0076 (7) | 0.0127 (6) |
C16 | 0.0493 (7) | 0.0448 (7) | 0.0423 (7) | 0.0080 (5) | 0.0011 (5) | 0.0123 (5) |
C17 | 0.0764 (10) | 0.0545 (8) | 0.0418 (7) | −0.0044 (7) | 0.0193 (7) | 0.0085 (6) |
C18 | 0.0783 (11) | 0.0580 (9) | 0.0704 (10) | 0.0076 (8) | 0.0327 (9) | 0.0105 (8) |
C19 | 0.0515 (8) | 0.0451 (7) | 0.0420 (7) | 0.0140 (6) | −0.0013 (5) | 0.0065 (5) |
O1—C10 | 1.2161 (16) | C13—C14 | 1.376 (2) |
N1—C6 | 1.4644 (16) | C14—C15 | 1.371 (2) |
N1—C7 | 1.4086 (16) | C15—C16 | 1.381 (2) |
N1—C10 | 1.3830 (16) | C17—C18 | 1.517 (3) |
N2—C19 | 1.136 (2) | C1—H1 | 0.9297 |
C1—C2 | 1.372 (2) | C2—H2 | 0.9295 |
C1—C9 | 1.395 (2) | C3—H3 | 0.9295 |
C2—C3 | 1.376 (2) | C6—H6 | 0.952 (16) |
C3—C4 | 1.402 (2) | C7—H7 | 0.9297 |
C4—C5 | 1.3966 (18) | C8—H8 | 0.9298 |
C4—C17 | 1.508 (2) | C12—H12 | 0.9297 |
C5—C6 | 1.5150 (18) | C13—H13 | 0.9297 |
C5—C9 | 1.3998 (18) | C14—H14 | 0.9295 |
C6—C19 | 1.488 (2) | C15—H15 | 0.9304 |
C7—C8 | 1.3298 (18) | C16—H16 | 0.9298 |
C8—C9 | 1.4577 (18) | C17—H17A | 0.9697 |
C10—C11 | 1.4875 (18) | C17—H17B | 0.9699 |
C11—C12 | 1.3909 (19) | C18—H18A | 0.9599 |
C11—C16 | 1.384 (2) | C18—H18B | 0.9595 |
C12—C13 | 1.382 (2) | C18—H18C | 0.9601 |
O1···C8i | 3.4083 (17) | C19···H18Cx | 3.0932 |
O1···C19 | 3.1458 (19) | H1···O1v | 2.6766 |
O1···H1i | 2.6766 | H1···H8 | 2.5458 |
O1···H6 | 2.297 (16) | H2···H14xi | 2.5152 |
O1···H8i | 2.5682 | H3···H17B | 2.3539 |
O1···H12 | 2.7188 | H6···O1 | 2.297 (16) |
O1···H12ii | 2.6267 | H6···C17 | 2.635 (16) |
N2···C15iii | 3.401 (2) | H6···C18 | 2.965 (17) |
N1···H16 | 2.8139 | H6···H17A | 2.2203 |
N2···H15iii | 2.8074 | H6···H18A | 2.4331 |
N2···H7iv | 2.8264 | H7···C11 | 2.6808 |
C6···C18 | 3.375 (2) | H7···C16 | 2.7713 |
C7···C7iv | 3.4726 (19) | H7···N2iv | 2.8264 |
C7···C16 | 3.124 (2) | H7···C19iv | 3.0707 |
C8···C19 | 3.337 (2) | H7···H15viii | 2.5735 |
C8···O1v | 3.4083 (17) | H8···O1v | 2.5682 |
C15···N2vi | 3.401 (2) | H8···H1 | 2.5458 |
C16···C7 | 3.124 (2) | H12···O1 | 2.7188 |
C18···C19 | 3.458 (2) | H12···O1ii | 2.6267 |
C18···C6 | 3.375 (2) | H14···H2xii | 2.5152 |
C19···C8 | 3.337 (2) | H15···N2vi | 2.8074 |
C19···O1 | 3.1458 (19) | H15···C7viii | 2.9866 |
C19···C18 | 3.458 (2) | H15···H7viii | 2.5735 |
C1···H17Avii | 3.0312 | H16···N1 | 2.8139 |
C5···H18A | 3.0963 | H16···C7 | 2.8058 |
C6···H18A | 2.8026 | H17A···C6 | 2.8270 |
C6···H17A | 2.8270 | H17A···H6 | 2.2203 |
C7···H16 | 2.8058 | H17A···C1vii | 3.0312 |
C7···H15viii | 2.9866 | H17B···H3 | 2.3539 |
C11···H7 | 2.6808 | H18A···C5 | 3.0963 |
C13···H18Bix | 3.0669 | H18A···C6 | 2.8026 |
C14···H18Bix | 3.0034 | H18A···C19 | 2.6346 |
C16···H7 | 2.7713 | H18A···H6 | 2.4331 |
C17···H6 | 2.635 (16) | H18B···C13xiii | 3.0669 |
C18···H6 | 2.965 (17) | H18B···C14xiii | 3.0034 |
C18···H18Cx | 3.0853 | H18C···C18x | 3.0853 |
C19···H18A | 2.6346 | H18C···C19x | 3.0932 |
C19···H7iv | 3.0707 | H18C···H18Cx | 2.5755 |
C6—N1—C7 | 116.28 (10) | C9—C1—H1 | 120.15 |
C6—N1—C10 | 116.35 (10) | C1—C2—H2 | 119.61 |
C7—N1—C10 | 124.71 (10) | C3—C2—H2 | 119.63 |
C2—C1—C9 | 119.75 (14) | C2—C3—H3 | 119.14 |
C1—C2—C3 | 120.75 (15) | C4—C3—H3 | 119.12 |
C2—C3—C4 | 121.73 (14) | N1—C6—H6 | 108.1 (10) |
C3—C4—C5 | 116.80 (13) | C5—C6—H6 | 112.1 (10) |
C3—C4—C17 | 120.35 (12) | C19—C6—H6 | 106.7 (10) |
C5—C4—C17 | 122.84 (13) | N1—C7—H7 | 119.58 |
C4—C5—C6 | 121.65 (12) | C8—C7—H7 | 119.57 |
C4—C5—C9 | 121.83 (12) | C7—C8—H8 | 119.44 |
C6—C5—C9 | 116.42 (11) | C9—C8—H8 | 119.43 |
N1—C6—C5 | 111.72 (10) | C11—C12—H12 | 120.17 |
N1—C6—C19 | 108.87 (10) | C13—C12—H12 | 120.22 |
C5—C6—C19 | 109.26 (11) | C12—C13—H13 | 119.88 |
N1—C7—C8 | 120.86 (12) | C14—C13—H13 | 119.87 |
C7—C8—C9 | 121.13 (12) | C13—C14—H14 | 119.95 |
C1—C9—C5 | 119.06 (12) | C15—C14—H14 | 119.92 |
C1—C9—C8 | 122.04 (12) | C14—C15—H15 | 119.79 |
C5—C9—C8 | 118.72 (11) | C16—C15—H15 | 119.78 |
O1—C10—N1 | 119.64 (12) | C11—C16—H16 | 120.13 |
O1—C10—C11 | 121.78 (12) | C15—C16—H16 | 120.09 |
N1—C10—C11 | 118.56 (11) | C4—C17—H17A | 108.32 |
C10—C11—C12 | 117.94 (12) | C4—C17—H17B | 108.33 |
C10—C11—C16 | 121.96 (11) | C18—C17—H17A | 108.28 |
C12—C11—C16 | 119.77 (12) | C18—C17—H17B | 108.29 |
C11—C12—C13 | 119.61 (14) | H17A—C17—H17B | 107.42 |
C12—C13—C14 | 120.26 (15) | C17—C18—H18A | 109.43 |
C13—C14—C15 | 120.14 (15) | C17—C18—H18B | 109.46 |
C14—C15—C16 | 120.43 (15) | C17—C18—H18C | 109.43 |
C11—C16—C15 | 119.78 (13) | H18A—C18—H18B | 109.50 |
C4—C17—C18 | 115.89 (13) | H18A—C18—H18C | 109.50 |
N2—C19—C6 | 177.79 (16) | H18B—C18—H18C | 109.51 |
C2—C1—H1 | 120.10 | ||
C7—N1—C6—C5 | 43.48 (14) | C4—C5—C9—C8 | −172.67 (13) |
C7—N1—C6—C19 | −77.28 (14) | C6—C5—C9—C1 | −173.80 (13) |
C10—N1—C6—C5 | −154.13 (11) | C6—C5—C9—C8 | 10.84 (19) |
C10—N1—C6—C19 | 85.12 (14) | C4—C5—C6—C19 | −93.33 (15) |
C6—N1—C7—C8 | −22.81 (18) | C9—C5—C6—N1 | −37.36 (16) |
C10—N1—C7—C8 | 176.44 (13) | C9—C5—C6—C19 | 83.17 (14) |
C6—N1—C10—O1 | −2.57 (18) | C4—C5—C9—C1 | 2.7 (2) |
C6—N1—C10—C11 | 175.59 (11) | N1—C7—C8—C9 | −6.4 (2) |
C7—N1—C10—O1 | 158.17 (13) | C7—C8—C9—C5 | 12.3 (2) |
C7—N1—C10—C11 | −23.67 (19) | C7—C8—C9—C1 | −162.93 (15) |
C2—C1—C9—C5 | −1.1 (2) | O1—C10—C11—C16 | 132.02 (15) |
C2—C1—C9—C8 | 174.15 (15) | N1—C10—C11—C12 | 140.61 (13) |
C9—C1—C2—C3 | −1.2 (3) | N1—C10—C11—C16 | −46.10 (18) |
C1—C2—C3—C4 | 1.9 (3) | O1—C10—C11—C12 | −41.28 (19) |
C2—C3—C4—C17 | −179.25 (16) | C10—C11—C12—C13 | 173.43 (13) |
C2—C3—C4—C5 | −0.3 (2) | C16—C11—C12—C13 | 0.0 (2) |
C17—C4—C5—C9 | 176.92 (14) | C10—C11—C16—C15 | −171.86 (13) |
C17—C4—C5—C6 | −6.8 (2) | C12—C11—C16—C15 | 1.3 (2) |
C3—C4—C5—C6 | 174.32 (13) | C11—C12—C13—C14 | −1.1 (2) |
C3—C4—C17—C18 | −105.68 (17) | C12—C13—C14—C15 | 0.9 (2) |
C5—C4—C17—C18 | 75.46 (19) | C13—C14—C15—C16 | 0.4 (2) |
C3—C4—C5—C9 | −2.0 (2) | C14—C15—C16—C11 | −1.5 (2) |
C4—C5—C6—N1 | 146.14 (12) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) x, y+1, z; (vii) −x+1, −y+1, −z; (viii) −x+1, −y+2, −z+1; (ix) x, y+1, z+1; (x) −x+1, −y, −z; (xi) x−1, y−1, z−1; (xii) x+1, y+1, z+1; (xiii) x, y−1, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.952 (16) | 2.297 (16) | 2.6471 (17) | 100.9 (11) |
C8—H8···O1v | 0.93 | 2.57 | 3.4083 (17) | 151 |
Symmetry code: (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H16N2O |
Mr | 288.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.996 (1), 8.948 (1), 11.297 (2) |
α, β, γ (°) | 108.51 (2), 94.86 (1), 93.04 (1) |
V (Å3) | 761.0 (2) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.25 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | Analytical (de Meulenaer & Tompa, 1965) |
Tmin, Tmax | 0.870, 0.912 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3363, 3129, 2863 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.627 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.133, 1.07 |
No. of reflections | 3129 |
No. of parameters | 204 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.27 |
Computer programs: locally modified CAD-4 Software (Enraf–Nonius, 1989), SET4 (de Boer & Duisenberg, 1984), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
O1—C10 | 1.2161 (16) | N1—C10 | 1.3830 (16) |
N1—C6 | 1.4644 (16) | N2—C19 | 1.136 (2) |
N1—C7 | 1.4086 (16) | ||
C6—N1—C7 | 116.28 (10) | N1—C7—C8 | 120.86 (12) |
C6—N1—C10 | 116.35 (10) | O1—C10—N1 | 119.64 (12) |
C7—N1—C10 | 124.71 (10) | O1—C10—C11 | 121.78 (12) |
N1—C6—C5 | 111.72 (10) | N1—C10—C11 | 118.56 (11) |
N1—C6—C19 | 108.87 (10) | N2—C19—C6 | 177.79 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.952 (16) | 2.297 (16) | 2.6471 (17) | 100.9 (11) |
C8—H8···O1i | 0.9300 | 2.5700 | 3.4083 (17) | 151.00 |
Symmetry code: (i) x−1, y, z. |
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Reissert compounds are of major synthetic interest as reagents for different synthetic pathways, such as alkylation, condensation with aldehydes and ketones, rearrangements and conjugate additions (Cooney, 1983).
2-Benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, is a Reissert compound. As expected, bond lengths and angles are similar to those observed in the analogue with no ethyl group at C4 (Tykarska et al., 1985). All bond lengths of the nitrogen-containing six-membered ring of the isoquinoline group are different, ranging from 1.330 (2) Å to 1.515 (2) Å and are significantly different from those observed in the tetrahydrogenated non-ethylated derivative (Pływaczyk et al., 1984). Bond angles at N1, C5, C7, C8, C9 (ranging from 116.3 (1)° to 121.1 (1)°) are typical for sp2 hybridization. The N1—C6—C5 angle is significantly smaller (111.7 (1)°), approaching, as expected, the classical value for an sp3 hybridization. The heterocyclic ring molecule exhibits a 1,3-diplanar conformation.
The phenyl ring is connected to the isoquinoline unit via an amide bond that adopts an anti conformation with respect to the adjacent C7—N1 bond. Coplanarity of the aromatic system of the isoquinoline moiety and the amide group allows maximum conjugation. In contrast, the amide group and the phenyl ring are not conjugated, with an N1—C10—C11—C12 torsion angle of 140.6 (1)°. A similar conformation is observed for the unsubstituted analogue, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline.
Interestingly, the ethyl group is almost perpendicular to the dihydroisoquinoline system (C3—C4—C17—C18 = -105.7 (2)°) and points in the same direction as the cyano group.