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organic compounds
4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile
aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the molecule of the title compound, C21H14N2O3, the tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH2CH2– fragment, the benzene ring and the pyridine ring being twisted by 24.3 (1)°. The ring of the benzodioxol system is bent away from the pyridine ring by 61.4 (1)° in order to avoid crowding the cyanide substituent. Two molecules are linked by a pair of N—H⋯O hydrogen bonds to form a centrosymmetric dimer.
Related literature
For background to the anticancer properties of this class of compounds, see: Rostom et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: X-SEED (Barbour, 2001
); software used to prepare material for publication: publCIF (Westrip, 2010
).
Supporting information
10.1107/S1600536811033903/xu5293sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811033903/xu5293Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811033903/xu5293Isup3.cml
A mixture of piperonaldehyde (1.50 g, 10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, and the yellow precipitate that formed was filtered, washed with water, dried and recrystallized from ethanol; m.p. 593–595 K.
Carbon- and nitrogen-bound H atoms were placed in calculated positions [C—H 0.95 to 0.99 Å, Uiso(H) = 1.2Ueq(C)] and were included in the
in the riding model approximation.The amino H atom was located in a difference Fourier map and was freely refined.
Data collection: CrysAlis PRO (Agilent, 2010); cell
CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010). ![]() | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C21H14N2O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
C21H14N2O3 | F(000) = 712 |
Mr = 342.34 | Dx = 1.386 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2yn | Cell parameters from 3826 reflections |
a = 7.6586 (3) Å | θ = 3.4–74.1° |
b = 16.5858 (5) Å | µ = 0.77 mm−1 |
c = 13.3220 (6) Å | T = 100 K |
β = 104.164 (4)° | Prism, yellow |
V = 1640.77 (11) Å3 | 0.30 × 0.20 × 0.05 mm |
Z = 4 |
Agilent SuperNova Dual diffractometer with Atlas detector | 3241 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2962 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.014 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 74.3°, θmin = 4.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −20→18 |
Tmin = 0.802, Tmax = 0.963 | l = −12→16 |
6078 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3916P] where P = (Fo2 + 2Fc2)/3 |
3241 reflections | (Δ/σ)max = 0.001 |
239 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C21H14N2O3 | V = 1640.77 (11) Å3 |
Mr = 342.34 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 7.6586 (3) Å | µ = 0.77 mm−1 |
b = 16.5858 (5) Å | T = 100 K |
c = 13.3220 (6) Å | 0.30 × 0.20 × 0.05 mm |
β = 104.164 (4)° |
Agilent SuperNova Dual diffractometer with Atlas detector | 3241 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 2962 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 0.963 | Rint = 0.014 |
6078 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.21 e Å−3 |
3241 reflections | Δρmin = −0.22 e Å−3 |
239 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.70432 (10) | 0.53335 (5) | 0.56250 (6) | 0.0240 (2) | |
O2 | 1.17132 (13) | 0.94538 (6) | 0.60416 (10) | 0.0444 (3) | |
O3 | 1.07114 (12) | 1.02058 (5) | 0.72509 (8) | 0.0325 (2) | |
N1 | 0.46189 (12) | 0.61383 (6) | 0.49726 (7) | 0.0200 (2) | |
H1 | 0.400 (2) | 0.5663 (10) | 0.4755 (12) | 0.036 (4)* | |
N2 | 1.07002 (14) | 0.65042 (6) | 0.67925 (9) | 0.0305 (3) | |
C1 | 0.38331 (15) | 0.68751 (7) | 0.47365 (8) | 0.0197 (2) | |
C2 | 0.19123 (15) | 0.69051 (7) | 0.41849 (9) | 0.0210 (2) | |
C3 | 0.07235 (15) | 0.62711 (7) | 0.42051 (9) | 0.0233 (2) | |
H3 | 0.1138 | 0.5799 | 0.4594 | 0.028* | |
C4 | −0.10680 (16) | 0.63304 (7) | 0.36557 (10) | 0.0270 (3) | |
H4 | −0.1877 | 0.5899 | 0.3671 | 0.032* | |
C5 | −0.16769 (16) | 0.70217 (8) | 0.30833 (10) | 0.0288 (3) | |
H5 | −0.2899 | 0.7060 | 0.2705 | 0.035* | |
C6 | −0.05002 (16) | 0.76546 (7) | 0.30652 (9) | 0.0268 (3) | |
H6 | −0.0922 | 0.8124 | 0.2672 | 0.032* | |
C7 | 0.12963 (16) | 0.76085 (7) | 0.36181 (9) | 0.0232 (2) | |
C8 | 0.26177 (16) | 0.82766 (7) | 0.36083 (10) | 0.0282 (3) | |
H8A | 0.1958 | 0.8789 | 0.3413 | 0.034* | |
H8B | 0.3302 | 0.8158 | 0.3084 | 0.034* | |
C9 | 0.39269 (16) | 0.83692 (7) | 0.46727 (10) | 0.0271 (3) | |
H9A | 0.4852 | 0.8778 | 0.4636 | 0.032* | |
H9B | 0.3266 | 0.8555 | 0.5182 | 0.032* | |
C10 | 0.48223 (15) | 0.75711 (7) | 0.50141 (9) | 0.0210 (2) | |
C11 | 0.66347 (15) | 0.75062 (7) | 0.55957 (9) | 0.0212 (2) | |
C12 | 0.74037 (15) | 0.67503 (7) | 0.57985 (9) | 0.0212 (2) | |
C13 | 0.63948 (15) | 0.60256 (7) | 0.54712 (8) | 0.0201 (2) | |
C14 | 0.92402 (15) | 0.66289 (7) | 0.63508 (9) | 0.0228 (3) | |
C15 | 0.76691 (15) | 0.82441 (6) | 0.60147 (9) | 0.0213 (2) | |
C16 | 0.92690 (16) | 0.84474 (7) | 0.57344 (10) | 0.0252 (3) | |
H16 | 0.9722 | 0.8130 | 0.5261 | 0.030* | |
C17 | 1.01415 (15) | 0.91297 (7) | 0.61812 (10) | 0.0262 (3) | |
C18 | 0.95379 (16) | 0.95848 (7) | 0.68946 (9) | 0.0238 (2) | |
C19 | 0.79788 (16) | 0.94009 (7) | 0.71780 (9) | 0.0250 (3) | |
H19 | 0.7560 | 0.9718 | 0.7665 | 0.030* | |
C20 | 0.70363 (16) | 0.87202 (7) | 0.67114 (9) | 0.0239 (2) | |
H20 | 0.5935 | 0.8579 | 0.6875 | 0.029* | |
C21 | 1.20431 (18) | 1.01643 (8) | 0.66633 (11) | 0.0346 (3) | |
H21A | 1.1967 | 1.0647 | 0.6218 | 0.041* | |
H21B | 1.3263 | 1.0143 | 0.7134 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0226 (4) | 0.0149 (4) | 0.0296 (4) | 0.0014 (3) | −0.0028 (3) | 0.0014 (3) |
O2 | 0.0336 (5) | 0.0346 (5) | 0.0716 (8) | −0.0158 (4) | 0.0256 (5) | −0.0236 (5) |
O3 | 0.0289 (4) | 0.0224 (4) | 0.0442 (5) | −0.0065 (3) | 0.0051 (4) | −0.0121 (4) |
N1 | 0.0196 (5) | 0.0147 (4) | 0.0226 (5) | −0.0005 (4) | −0.0007 (4) | −0.0004 (4) |
N2 | 0.0250 (5) | 0.0230 (5) | 0.0375 (6) | 0.0003 (4) | −0.0040 (4) | −0.0018 (4) |
C1 | 0.0213 (5) | 0.0186 (5) | 0.0181 (5) | 0.0018 (4) | 0.0027 (4) | −0.0002 (4) |
C2 | 0.0204 (5) | 0.0203 (5) | 0.0205 (5) | 0.0026 (4) | 0.0018 (4) | −0.0029 (4) |
C3 | 0.0224 (5) | 0.0219 (6) | 0.0240 (6) | 0.0024 (4) | 0.0027 (4) | −0.0020 (4) |
C4 | 0.0216 (5) | 0.0269 (6) | 0.0306 (6) | −0.0011 (5) | 0.0028 (5) | −0.0049 (5) |
C5 | 0.0209 (5) | 0.0296 (6) | 0.0316 (6) | 0.0046 (5) | −0.0019 (5) | −0.0058 (5) |
C6 | 0.0250 (6) | 0.0229 (6) | 0.0281 (6) | 0.0067 (5) | −0.0022 (5) | −0.0018 (5) |
C7 | 0.0234 (5) | 0.0209 (5) | 0.0235 (5) | 0.0030 (4) | 0.0021 (4) | −0.0032 (4) |
C8 | 0.0254 (6) | 0.0209 (6) | 0.0338 (7) | 0.0033 (4) | −0.0013 (5) | 0.0056 (5) |
C9 | 0.0245 (6) | 0.0164 (5) | 0.0362 (7) | 0.0022 (4) | −0.0005 (5) | −0.0007 (5) |
C10 | 0.0218 (5) | 0.0174 (5) | 0.0226 (5) | 0.0020 (4) | 0.0031 (4) | −0.0010 (4) |
C11 | 0.0233 (5) | 0.0181 (5) | 0.0211 (5) | 0.0002 (4) | 0.0031 (4) | −0.0015 (4) |
C12 | 0.0200 (5) | 0.0189 (5) | 0.0219 (5) | −0.0004 (4) | −0.0003 (4) | 0.0000 (4) |
C13 | 0.0210 (5) | 0.0181 (5) | 0.0190 (5) | 0.0012 (4) | 0.0007 (4) | 0.0010 (4) |
C14 | 0.0250 (6) | 0.0150 (5) | 0.0260 (6) | −0.0006 (4) | 0.0016 (5) | −0.0020 (4) |
C15 | 0.0226 (5) | 0.0157 (5) | 0.0222 (5) | 0.0007 (4) | −0.0010 (4) | −0.0002 (4) |
C16 | 0.0243 (5) | 0.0214 (6) | 0.0291 (6) | 0.0003 (4) | 0.0050 (5) | −0.0060 (5) |
C17 | 0.0219 (5) | 0.0217 (6) | 0.0343 (6) | −0.0022 (4) | 0.0054 (5) | −0.0026 (5) |
C18 | 0.0267 (6) | 0.0147 (5) | 0.0258 (6) | −0.0017 (4) | −0.0015 (4) | −0.0020 (4) |
C19 | 0.0315 (6) | 0.0195 (5) | 0.0232 (6) | 0.0009 (4) | 0.0051 (5) | −0.0026 (4) |
C20 | 0.0266 (6) | 0.0189 (5) | 0.0255 (6) | −0.0012 (4) | 0.0050 (5) | 0.0000 (4) |
C21 | 0.0342 (7) | 0.0237 (6) | 0.0449 (8) | −0.0085 (5) | 0.0081 (6) | −0.0066 (6) |
O1—C13 | 1.2477 (14) | C8—C9 | 1.5309 (17) |
O2—C17 | 1.3718 (15) | C8—H8A | 0.9900 |
O2—C21 | 1.4269 (16) | C8—H8B | 0.9900 |
O3—C18 | 1.3730 (14) | C9—C10 | 1.5088 (15) |
O3—C21 | 1.4312 (17) | C9—H9A | 0.9900 |
N1—C1 | 1.3645 (14) | C9—H9B | 0.9900 |
N1—C13 | 1.3725 (14) | C10—C11 | 1.4185 (15) |
N1—H1 | 0.931 (17) | C11—C12 | 1.3834 (15) |
N2—C14 | 1.1477 (15) | C11—C15 | 1.4902 (15) |
C1—C10 | 1.3807 (15) | C12—C14 | 1.4331 (15) |
C1—C2 | 1.4756 (15) | C12—C13 | 1.4377 (15) |
C2—C3 | 1.3955 (16) | C15—C20 | 1.3928 (16) |
C2—C7 | 1.4068 (16) | C15—C16 | 1.4065 (17) |
C3—C4 | 1.3916 (16) | C16—C17 | 1.3736 (16) |
C3—H3 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.3928 (18) | C17—C18 | 1.3790 (17) |
C4—H4 | 0.9500 | C18—C19 | 1.3718 (17) |
C5—C6 | 1.3875 (18) | C19—C20 | 1.4010 (16) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.3948 (15) | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—H21A | 0.9900 |
C7—C8 | 1.5029 (17) | C21—H21B | 0.9900 |
C17—O2—C21 | 106.35 (10) | C1—C10—C11 | 118.83 (10) |
C18—O3—C21 | 105.58 (9) | C1—C10—C9 | 118.27 (10) |
C1—N1—C13 | 124.23 (9) | C11—C10—C9 | 122.89 (10) |
C1—N1—H1 | 121.6 (10) | C12—C11—C10 | 119.24 (10) |
C13—N1—H1 | 114.0 (10) | C12—C11—C15 | 120.61 (10) |
N1—C1—C10 | 120.33 (10) | C10—C11—C15 | 120.11 (10) |
N1—C1—C2 | 118.34 (10) | C11—C12—C14 | 123.03 (10) |
C10—C1—C2 | 121.33 (10) | C11—C12—C13 | 121.79 (10) |
C3—C2—C7 | 120.03 (10) | C14—C12—C13 | 115.17 (10) |
C3—C2—C1 | 122.72 (10) | O1—C13—N1 | 120.82 (10) |
C7—C2—C1 | 117.25 (10) | O1—C13—C12 | 123.82 (10) |
C4—C3—C2 | 120.04 (11) | N1—C13—C12 | 115.36 (9) |
C4—C3—H3 | 120.0 | N2—C14—C12 | 177.69 (12) |
C2—C3—H3 | 120.0 | C20—C15—C16 | 120.58 (10) |
C5—C4—C3 | 120.07 (11) | C20—C15—C11 | 118.39 (10) |
C5—C4—H4 | 120.0 | C16—C15—C11 | 121.02 (10) |
C3—C4—H4 | 120.0 | C17—C16—C15 | 116.46 (11) |
C6—C5—C4 | 120.03 (11) | C17—C16—H16 | 121.8 |
C6—C5—H5 | 120.0 | C15—C16—H16 | 121.8 |
C4—C5—H5 | 120.0 | O2—C17—C16 | 127.88 (11) |
C5—C6—C7 | 120.68 (11) | O2—C17—C18 | 109.40 (10) |
C5—C6—H6 | 119.7 | C16—C17—C18 | 122.68 (11) |
C7—C6—H6 | 119.7 | O3—C18—C19 | 127.72 (11) |
C6—C7—C2 | 119.13 (11) | O3—C18—C17 | 110.33 (11) |
C6—C7—C8 | 122.30 (10) | C19—C18—C17 | 121.95 (11) |
C2—C7—C8 | 118.55 (10) | C18—C19—C20 | 116.47 (11) |
C7—C8—C9 | 110.84 (10) | C18—C19—H19 | 121.8 |
C7—C8—H8A | 109.5 | C20—C19—H19 | 121.8 |
C9—C8—H8A | 109.5 | C15—C20—C19 | 121.81 (11) |
C7—C8—H8B | 109.5 | C15—C20—H20 | 119.1 |
C9—C8—H8B | 109.5 | C19—C20—H20 | 119.1 |
H8A—C8—H8B | 108.1 | O2—C21—O3 | 107.97 (10) |
C10—C9—C8 | 109.72 (10) | O2—C21—H21A | 110.1 |
C10—C9—H9A | 109.7 | O3—C21—H21A | 110.1 |
C8—C9—H9A | 109.7 | O2—C21—H21B | 110.1 |
C10—C9—H9B | 109.7 | O3—C21—H21B | 110.1 |
C8—C9—H9B | 109.7 | H21A—C21—H21B | 108.4 |
H9A—C9—H9B | 108.2 | ||
C13—N1—C1—C10 | −1.05 (17) | C10—C11—C12—C13 | −2.52 (17) |
C13—N1—C1—C2 | 179.18 (10) | C15—C11—C12—C13 | 175.21 (10) |
N1—C1—C2—C3 | 22.74 (16) | C1—N1—C13—O1 | −177.03 (10) |
C10—C1—C2—C3 | −157.03 (11) | C1—N1—C13—C12 | 3.52 (16) |
N1—C1—C2—C7 | −156.96 (10) | C11—C12—C13—O1 | 178.92 (11) |
C10—C1—C2—C7 | 23.27 (16) | C14—C12—C13—O1 | −1.53 (17) |
C7—C2—C3—C4 | 0.69 (17) | C11—C12—C13—N1 | −1.66 (16) |
C1—C2—C3—C4 | −179.00 (10) | C14—C12—C13—N1 | 177.90 (10) |
C2—C3—C4—C5 | 0.11 (18) | C12—C11—C15—C20 | −116.89 (13) |
C3—C4—C5—C6 | −0.38 (19) | C10—C11—C15—C20 | 60.82 (15) |
C4—C5—C6—C7 | −0.15 (19) | C12—C11—C15—C16 | 61.65 (16) |
C5—C6—C7—C2 | 0.94 (17) | C10—C11—C15—C16 | −120.64 (12) |
C5—C6—C7—C8 | 179.27 (12) | C20—C15—C16—C17 | −0.08 (17) |
C3—C2—C7—C6 | −1.21 (17) | C11—C15—C16—C17 | −178.59 (11) |
C1—C2—C7—C6 | 178.50 (10) | C21—O2—C17—C16 | 179.29 (13) |
C3—C2—C7—C8 | −179.60 (11) | C21—O2—C17—C18 | −2.82 (15) |
C1—C2—C7—C8 | 0.11 (16) | C15—C16—C17—O2 | 179.76 (12) |
C6—C7—C8—C9 | 143.06 (11) | C15—C16—C17—C18 | 2.13 (18) |
C2—C7—C8—C9 | −38.60 (15) | C21—O3—C18—C19 | −176.17 (12) |
C7—C8—C9—C10 | 54.40 (14) | C21—O3—C18—C17 | 4.47 (13) |
N1—C1—C10—C11 | −3.38 (17) | O2—C17—C18—O3 | −1.08 (14) |
C2—C1—C10—C11 | 176.38 (10) | C16—C17—C18—O3 | 176.94 (11) |
N1—C1—C10—C9 | 175.95 (10) | O2—C17—C18—C19 | 179.52 (11) |
C2—C1—C10—C9 | −4.29 (16) | C16—C17—C18—C19 | −2.46 (19) |
C8—C9—C10—C1 | −34.42 (15) | O3—C18—C19—C20 | −178.70 (11) |
C8—C9—C10—C11 | 144.89 (11) | C17—C18—C19—C20 | 0.59 (17) |
C1—C10—C11—C12 | 5.05 (17) | C16—C15—C20—C19 | −1.71 (17) |
C9—C10—C11—C12 | −174.25 (11) | C11—C15—C20—C19 | 176.83 (10) |
C1—C10—C11—C15 | −172.70 (10) | C18—C19—C20—C15 | 1.44 (17) |
C9—C10—C11—C15 | 8.01 (17) | C17—O2—C21—O3 | 5.54 (15) |
C10—C11—C12—C14 | 177.96 (10) | C18—O3—C21—O2 | −6.13 (14) |
C15—C11—C12—C14 | −4.31 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.93 (2) | 1.85 (2) | 2.778 (1) | 175 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H14N2O3 |
Mr | 342.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 7.6586 (3), 16.5858 (5), 13.3220 (6) |
β (°) | 104.164 (4) |
V (Å3) | 1640.77 (11) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.77 |
Crystal size (mm) | 0.30 × 0.20 × 0.05 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.802, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6078, 3241, 2962 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.100, 1.02 |
No. of reflections | 3241 |
No. of parameters | 239 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.93 (2) | 1.85 (2) | 2.778 (1) | 175 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank King Abdulaziz University and the University of Malaya for supporting this study.
References
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Rostom, S. A. F., Faidallah, H. M. & Al-Saadi, M. S. (2011). Med. Chem. Res. 20 (DOI: 10.1007/s00044-010-9469-0). Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The compound (Scheme I) belongs to a series of cyano-pyridinones that have been evaluated for their anticancer properties (Rostom et al., 2011). The tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH2CH2– fragment, the benzene ring and the pyridine ring being twisted by 24.3 (1)°. The 4-subsituted aromatic ring is bent away from the pyridine ring by 61.4 (1) ° in order to avoid crowding the cyanide substituent (Fig. 1). Two molecules are linked by an N—H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).