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The structure of 4-(naphthalen-2-yl)-2-oxo-6-phenyl-1,2-di­hydro­pyridine-3-carbo­nitrile, prepared by a three-component one-pot reaction, is based on dimers connected by N—H...O hydrogen bonds, which also inter­act through π–π contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009180/dj2070sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009180/dj2070Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989023009180/dj2070Isup3.cdx
Supplementary material

cdx

Chemdraw file https://doi.org/10.1107/S2056989023009180/dj2070Isup4.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009180/dj2070Isup5.cml
Supplementary material

CCDC reference: 2302104

Computing details top

Data collection: APEX3 (Bruker, 2019); cell refinement: SAINT V8.40A (Bruker, 2019); data reduction: SAINT V8.40A (Bruker, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

4-(Naphthalen-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile top
Crystal data top
C22H14N2OF(000) = 672
Mr = 322.35Dx = 1.339 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.0845 (4) ÅCell parameters from 7569 reflections
b = 10.4369 (6) Åθ = 2.7–26.3°
c = 21.6298 (11) ŵ = 0.08 mm1
β = 91.878 (2)°T = 298 K
V = 1598.45 (15) Å3Block, yellow
Z = 40.34 × 0.26 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
2531 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.056
φ and ω scansθmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 88
Tmin = 0.655, Tmax = 0.745k = 1313
18613 measured reflectionsl = 2626
3250 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.7178P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3250 reflectionsΔρmax = 0.18 e Å3
230 parametersΔρmin = 0.21 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.82728 (17)0.39070 (12)0.51570 (6)0.0445 (3)
N10.8282 (2)0.59995 (14)0.54490 (6)0.0335 (3)
C60.7537 (2)0.70213 (16)0.57481 (8)0.0329 (4)
C20.7497 (2)0.47978 (16)0.54354 (8)0.0331 (4)
C480.0535 (2)0.45419 (16)0.68796 (8)0.0334 (4)
C600.8580 (2)0.82447 (16)0.57434 (8)0.0341 (4)
C40.5045 (2)0.56580 (17)0.61101 (8)0.0327 (4)
C30.5797 (2)0.46509 (16)0.57786 (8)0.0322 (4)
C410.1982 (2)0.46820 (17)0.64419 (8)0.0342 (4)
H410.1916230.4207000.6078040.041*
C400.3471 (2)0.55046 (16)0.65470 (8)0.0340 (4)
C50.5920 (2)0.68616 (17)0.60673 (8)0.0366 (4)
H50.5388430.7564460.6260380.044*
C610.7640 (3)0.93869 (17)0.56255 (8)0.0409 (4)
H610.6354290.9379480.5523190.049*
C490.0619 (2)0.52910 (18)0.74242 (8)0.0381 (4)
N310.4577 (3)0.23249 (18)0.58144 (10)0.0640 (5)
C420.0972 (2)0.36732 (18)0.67854 (9)0.0411 (4)
H420.1016080.3154990.6435460.049*
C651.0507 (3)0.82723 (19)0.58974 (9)0.0443 (5)
H651.1161420.7511800.5970290.053*
C470.3542 (3)0.62309 (19)0.71018 (9)0.0437 (5)
H470.4551120.6784370.7179900.052*
C450.0852 (3)0.51704 (19)0.78517 (9)0.0459 (5)
H450.0812730.5654350.8212870.055*
C620.8604 (3)1.05386 (18)0.56591 (10)0.0499 (5)
H620.7973541.1301750.5570740.060*
C300.5102 (2)0.33702 (19)0.58021 (9)0.0422 (5)
C430.2373 (3)0.3587 (2)0.72060 (9)0.0478 (5)
H430.3366780.3016910.7138120.057*
C460.2157 (3)0.61315 (19)0.75229 (9)0.0467 (5)
H460.2229020.6626010.7880550.056*
C440.2314 (3)0.4353 (2)0.77365 (9)0.0490 (5)
H440.3287520.4302770.8013780.059*
C631.0496 (3)1.0555 (2)0.58234 (10)0.0541 (6)
H631.1136581.1330870.5854650.065*
C641.1440 (3)0.9430 (2)0.59413 (11)0.0545 (5)
H641.2719450.9448290.6051680.065*
H10.937 (3)0.610 (2)0.5249 (10)0.053 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0441 (7)0.0351 (7)0.0557 (8)0.0034 (6)0.0221 (6)0.0099 (6)
N10.0315 (7)0.0344 (8)0.0352 (8)0.0007 (6)0.0113 (6)0.0002 (6)
C60.0349 (9)0.0320 (9)0.0320 (9)0.0030 (7)0.0059 (7)0.0001 (7)
C20.0339 (8)0.0335 (9)0.0321 (9)0.0007 (7)0.0062 (7)0.0006 (7)
C480.0313 (8)0.0351 (9)0.0341 (9)0.0028 (7)0.0032 (7)0.0049 (7)
C600.0378 (9)0.0335 (9)0.0316 (9)0.0009 (7)0.0124 (7)0.0017 (7)
C40.0289 (8)0.0372 (9)0.0322 (9)0.0016 (7)0.0049 (7)0.0018 (7)
C30.0306 (8)0.0337 (9)0.0326 (9)0.0018 (7)0.0045 (7)0.0019 (7)
C410.0349 (9)0.0365 (9)0.0315 (9)0.0020 (7)0.0064 (7)0.0016 (7)
C400.0317 (8)0.0353 (9)0.0355 (9)0.0019 (7)0.0076 (7)0.0014 (7)
C50.0366 (9)0.0322 (9)0.0417 (10)0.0027 (7)0.0130 (7)0.0022 (8)
C610.0408 (10)0.0387 (10)0.0441 (10)0.0038 (8)0.0126 (8)0.0003 (8)
C490.0398 (9)0.0406 (10)0.0345 (9)0.0030 (8)0.0085 (7)0.0028 (8)
N310.0523 (11)0.0456 (11)0.0951 (15)0.0076 (9)0.0158 (10)0.0058 (10)
C420.0389 (9)0.0437 (11)0.0406 (10)0.0026 (8)0.0018 (8)0.0007 (8)
C650.0406 (10)0.0400 (11)0.0526 (12)0.0025 (8)0.0060 (8)0.0039 (9)
C470.0408 (10)0.0473 (11)0.0436 (11)0.0099 (9)0.0091 (8)0.0063 (9)
C450.0489 (11)0.0520 (12)0.0377 (10)0.0004 (9)0.0142 (8)0.0008 (9)
C620.0655 (13)0.0310 (10)0.0546 (12)0.0045 (9)0.0220 (10)0.0019 (9)
C300.0347 (9)0.0432 (11)0.0494 (11)0.0003 (8)0.0102 (8)0.0032 (9)
C430.0388 (10)0.0557 (12)0.0494 (11)0.0077 (9)0.0057 (8)0.0098 (10)
C460.0526 (11)0.0510 (12)0.0373 (10)0.0099 (9)0.0130 (8)0.0124 (9)
C440.0411 (10)0.0631 (13)0.0438 (11)0.0025 (10)0.0166 (8)0.0126 (10)
C630.0601 (13)0.0418 (12)0.0618 (13)0.0143 (10)0.0225 (10)0.0150 (10)
C640.0412 (11)0.0548 (13)0.0680 (14)0.0081 (10)0.0082 (10)0.0142 (11)
Geometric parameters (Å, º) top
O2—C21.245 (2)C61—C621.383 (3)
N1—C61.363 (2)C49—C451.421 (2)
N1—C21.372 (2)C49—C461.410 (3)
N1—H10.90 (2)N31—C301.153 (3)
C6—C601.475 (2)C42—H420.9300
C6—C51.367 (2)C42—C431.371 (3)
C2—C31.444 (2)C65—H650.9300
C48—C411.425 (2)C65—C641.379 (3)
C48—C491.413 (3)C47—H470.9300
C48—C421.411 (2)C47—C461.364 (2)
C60—C611.385 (2)C45—H450.9300
C60—C651.395 (3)C45—C441.359 (3)
C4—C31.388 (2)C62—H620.9300
C4—C401.494 (2)C62—C631.375 (3)
C4—C51.405 (2)C43—H430.9300
C3—C301.426 (3)C43—C441.398 (3)
C41—H410.9300C46—H460.9300
C41—C401.373 (2)C44—H440.9300
C40—C471.419 (3)C63—H630.9300
C5—H50.9300C63—C641.370 (3)
C61—H610.9300C64—H640.9300
C6—N1—C2124.23 (14)C46—C49—C48118.80 (15)
C6—N1—H1119.1 (13)C46—C49—C45122.42 (17)
C2—N1—H1116.7 (13)C48—C42—H42119.8
N1—C6—C60118.17 (14)C43—C42—C48120.48 (18)
N1—C6—C5119.25 (16)C43—C42—H42119.8
C5—C6—C60122.49 (15)C60—C65—H65120.1
O2—C2—N1120.53 (15)C64—C65—C60119.83 (18)
O2—C2—C3123.93 (16)C64—C65—H65120.1
N1—C2—C3115.50 (15)C40—C47—H47119.4
C49—C48—C41119.03 (16)C46—C47—C40121.16 (17)
C42—C48—C41121.83 (16)C46—C47—H47119.4
C42—C48—C49119.14 (15)C49—C45—H45119.8
C61—C60—C6120.54 (16)C44—C45—C49120.49 (18)
C61—C60—C65119.16 (17)C44—C45—H45119.8
C65—C60—C6120.18 (16)C61—C62—H62120.0
C3—C4—C40123.54 (15)C63—C62—C61119.97 (19)
C3—C4—C5117.71 (14)C63—C62—H62120.0
C5—C4—C40118.54 (15)N31—C30—C3178.4 (2)
C4—C3—C2121.73 (15)C42—C43—H43119.8
C4—C3—C30123.54 (15)C42—C43—C44120.30 (18)
C30—C3—C2114.38 (15)C44—C43—H43119.8
C48—C41—H41119.4C49—C46—H46119.5
C40—C41—C48121.29 (16)C47—C46—C49121.03 (17)
C40—C41—H41119.4C47—C46—H46119.5
C41—C40—C4123.20 (15)C45—C44—C43120.75 (17)
C41—C40—C47118.67 (15)C45—C44—H44119.6
C47—C40—C4118.11 (15)C43—C44—H44119.6
C6—C5—C4121.42 (16)C62—C63—H63119.9
C6—C5—H5119.3C64—C63—C62120.21 (19)
C4—C5—H5119.3C64—C63—H63119.9
C60—C61—H61119.9C65—C64—H64119.7
C62—C61—C60120.29 (18)C63—C64—C65120.52 (19)
C62—C61—H61119.9C63—C64—H64119.7
C48—C49—C45118.78 (17)
O2—C2—C3—C4176.33 (17)C41—C48—C49—C461.4 (3)
O2—C2—C3—C303.0 (3)C41—C48—C42—C43178.05 (17)
N1—C6—C60—C61135.08 (17)C41—C40—C47—C460.7 (3)
N1—C6—C60—C6549.1 (2)C40—C4—C3—C2170.35 (16)
N1—C6—C5—C42.1 (3)C40—C4—C3—C302.4 (3)
N1—C2—C3—C41.4 (2)C40—C4—C5—C6170.28 (16)
N1—C2—C3—C30174.79 (15)C40—C47—C46—C490.8 (3)
C6—N1—C2—O2179.26 (16)C5—C6—C60—C6148.6 (2)
C6—N1—C2—C31.4 (2)C5—C6—C60—C65127.28 (19)
C6—C60—C61—C62176.01 (17)C5—C4—C3—C24.3 (2)
C6—C60—C65—C64174.71 (18)C5—C4—C3—C30177.09 (17)
C2—N1—C6—C60177.59 (15)C5—C4—C40—C41148.18 (17)
C2—N1—C6—C51.1 (3)C5—C4—C40—C4732.9 (2)
C48—C41—C40—C4178.35 (16)C61—C60—C65—C641.2 (3)
C48—C41—C40—C470.5 (3)C61—C62—C63—C641.4 (3)
C48—C49—C45—C440.3 (3)C49—C48—C41—C401.6 (3)
C48—C49—C46—C470.3 (3)C49—C48—C42—C432.2 (3)
C48—C42—C43—C440.6 (3)C49—C45—C44—C432.0 (3)
C60—C6—C5—C4174.25 (16)C42—C48—C41—C40178.13 (16)
C60—C61—C62—C631.4 (3)C42—C48—C49—C451.8 (3)
C60—C65—C64—C631.2 (3)C42—C48—C49—C46178.30 (17)
C4—C40—C47—C46179.62 (18)C42—C43—C44—C451.6 (3)
C3—C4—C40—C4137.2 (3)C65—C60—C61—C620.1 (3)
C3—C4—C40—C47141.73 (18)C45—C49—C46—C47179.63 (19)
C3—C4—C5—C64.7 (3)C62—C63—C64—C650.1 (3)
C41—C48—C49—C45178.47 (16)C46—C49—C45—C44179.63 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.90 (2)1.91 (2)2.8096 (18)172.8 (19)
Symmetry code: (i) x+2, y+1, z+1.
 

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