Crystal structure of 4-(naphthalen-2-yl)-2-oxo-6-phenyl-1,2-di­hydro­pyridine-3-carbo­nitrile

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.123
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.272 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C3       --C30      .        7.8 s.u.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C22H14N2O	F(000) = 672
Mr = 322.35	Dx = 1.339 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.0845 (4) Å	Cell parameters from 7569 reflections
b = 10.4369 (6) Å	θ = 2.7–26.3°
c = 21.6298 (11) Å	µ = 0.08 mm^−1
β = 91.878 (2)°	T = 298 K
V = 1598.45 (15) Å^3	Block, yellow
Z = 4	0.34 × 0.26 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	2531 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.056
φ and ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
Tmin = 0.655, Tmax = 0.745	k = −13→13
18613 measured reflections	l = −26→26
3250 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.7178P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3250 reflections	Δρmax = 0.18 e Å^−3
230 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.82728 (17)	0.39070 (12)	0.51570 (6)	0.0445 (3)
N1	0.8282 (2)	0.59995 (14)	0.54490 (6)	0.0335 (3)
C6	0.7537 (2)	0.70213 (16)	0.57481 (8)	0.0329 (4)
C2	0.7497 (2)	0.47978 (16)	0.54354 (8)	0.0331 (4)
C48	0.0535 (2)	0.45419 (16)	0.68796 (8)	0.0334 (4)
C60	0.8580 (2)	0.82447 (16)	0.57434 (8)	0.0341 (4)
C4	0.5045 (2)	0.56580 (17)	0.61101 (8)	0.0327 (4)
C3	0.5797 (2)	0.46509 (16)	0.57786 (8)	0.0322 (4)
C41	0.1982 (2)	0.46820 (17)	0.64419 (8)	0.0342 (4)
H41	0.191623	0.420700	0.607804	0.041*
C40	0.3471 (2)	0.55046 (16)	0.65470 (8)	0.0340 (4)
C5	0.5920 (2)	0.68616 (17)	0.60673 (8)	0.0366 (4)
H5	0.538843	0.756446	0.626038	0.044*
C61	0.7640 (3)	0.93869 (17)	0.56255 (8)	0.0409 (4)
H61	0.635429	0.937948	0.552319	0.049*
C49	0.0619 (2)	0.52910 (18)	0.74242 (8)	0.0381 (4)
N31	0.4577 (3)	0.23249 (18)	0.58144 (10)	0.0640 (5)
C42	−0.0972 (2)	0.36732 (18)	0.67854 (9)	0.0411 (4)
H42	−0.101608	0.315499	0.643546	0.049*
C65	1.0507 (3)	0.82723 (19)	0.58974 (9)	0.0443 (5)
H65	1.116142	0.751180	0.597029	0.053*
C47	0.3542 (3)	0.62309 (19)	0.71018 (9)	0.0437 (5)
H47	0.455112	0.678437	0.717990	0.052*
C45	−0.0852 (3)	0.51704 (19)	0.78517 (9)	0.0459 (5)
H45	−0.081273	0.565435	0.821287	0.055*
C62	0.8604 (3)	1.05386 (18)	0.56591 (10)	0.0499 (5)
H62	0.797354	1.130175	0.557074	0.060*
C30	0.5102 (2)	0.33702 (19)	0.58021 (9)	0.0422 (5)
C43	−0.2373 (3)	0.3587 (2)	0.72060 (9)	0.0478 (5)
H43	−0.336678	0.301691	0.713812	0.057*
C46	0.2157 (3)	0.61315 (19)	0.75229 (9)	0.0467 (5)
H46	0.222902	0.662601	0.788055	0.056*
C44	−0.2314 (3)	0.4353 (2)	0.77365 (9)	0.0490 (5)
H44	−0.328752	0.430277	0.801378	0.059*
C63	1.0496 (3)	1.0555 (2)	0.58234 (10)	0.0541 (6)
H63	1.113658	1.133087	0.585465	0.065*
C64	1.1440 (3)	0.9430 (2)	0.59413 (11)	0.0545 (5)
H64	1.271945	0.944829	0.605168	0.065*
H1	0.937 (3)	0.610 (2)	0.5249 (10)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0441 (7)	0.0351 (7)	0.0557 (8)	−0.0034 (6)	0.0221 (6)	−0.0099 (6)
N1	0.0315 (7)	0.0344 (8)	0.0352 (8)	−0.0007 (6)	0.0113 (6)	−0.0002 (6)
C6	0.0349 (9)	0.0320 (9)	0.0320 (9)	0.0030 (7)	0.0059 (7)	0.0001 (7)
C2	0.0339 (8)	0.0335 (9)	0.0321 (9)	0.0007 (7)	0.0062 (7)	−0.0006 (7)
C48	0.0313 (8)	0.0351 (9)	0.0341 (9)	0.0028 (7)	0.0032 (7)	0.0049 (7)
C60	0.0378 (9)	0.0335 (9)	0.0316 (9)	−0.0009 (7)	0.0124 (7)	−0.0017 (7)
C4	0.0289 (8)	0.0372 (9)	0.0322 (9)	0.0016 (7)	0.0049 (7)	0.0018 (7)
C3	0.0306 (8)	0.0337 (9)	0.0326 (9)	−0.0018 (7)	0.0045 (7)	0.0019 (7)
C41	0.0349 (9)	0.0365 (9)	0.0315 (9)	0.0020 (7)	0.0064 (7)	−0.0016 (7)
C40	0.0317 (8)	0.0353 (9)	0.0355 (9)	0.0019 (7)	0.0076 (7)	0.0014 (7)
C5	0.0366 (9)	0.0322 (9)	0.0417 (10)	0.0027 (7)	0.0130 (7)	−0.0022 (8)
C61	0.0408 (10)	0.0387 (10)	0.0441 (10)	0.0038 (8)	0.0126 (8)	0.0003 (8)
C49	0.0398 (9)	0.0406 (10)	0.0345 (9)	0.0030 (8)	0.0085 (7)	0.0028 (8)
N31	0.0523 (11)	0.0456 (11)	0.0951 (15)	−0.0076 (9)	0.0158 (10)	−0.0058 (10)
C42	0.0389 (9)	0.0437 (11)	0.0406 (10)	−0.0026 (8)	0.0018 (8)	0.0007 (8)
C65	0.0406 (10)	0.0400 (11)	0.0526 (12)	0.0025 (8)	0.0060 (8)	−0.0039 (9)
C47	0.0408 (10)	0.0473 (11)	0.0436 (11)	−0.0099 (9)	0.0091 (8)	−0.0063 (9)
C45	0.0489 (11)	0.0520 (12)	0.0377 (10)	0.0004 (9)	0.0142 (8)	0.0008 (9)
C62	0.0655 (13)	0.0310 (10)	0.0546 (12)	0.0045 (9)	0.0220 (10)	−0.0019 (9)
C30	0.0347 (9)	0.0432 (11)	0.0494 (11)	−0.0003 (8)	0.0102 (8)	−0.0032 (9)
C43	0.0388 (10)	0.0557 (12)	0.0494 (11)	−0.0077 (9)	0.0057 (8)	0.0098 (10)
C46	0.0526 (11)	0.0510 (12)	0.0373 (10)	−0.0099 (9)	0.0130 (8)	−0.0124 (9)
C44	0.0411 (10)	0.0631 (13)	0.0438 (11)	0.0025 (10)	0.0166 (8)	0.0126 (10)
C63	0.0601 (13)	0.0418 (12)	0.0618 (13)	−0.0143 (10)	0.0225 (10)	−0.0150 (10)
C64	0.0412 (11)	0.0548 (13)	0.0680 (14)	−0.0081 (10)	0.0082 (10)	−0.0142 (11)

Geometric parameters (Å, º)

O2—C2	1.245 (2)	C61—C62	1.383 (3)
N1—C6	1.363 (2)	C49—C45	1.421 (2)
N1—C2	1.372 (2)	C49—C46	1.410 (3)
N1—H1	0.90 (2)	N31—C30	1.153 (3)
C6—C60	1.475 (2)	C42—H42	0.9300
C6—C5	1.367 (2)	C42—C43	1.371 (3)
C2—C3	1.444 (2)	C65—H65	0.9300
C48—C41	1.425 (2)	C65—C64	1.379 (3)
C48—C49	1.413 (3)	C47—H47	0.9300
C48—C42	1.411 (2)	C47—C46	1.364 (2)
C60—C61	1.385 (2)	C45—H45	0.9300
C60—C65	1.395 (3)	C45—C44	1.359 (3)
C4—C3	1.388 (2)	C62—H62	0.9300
C4—C40	1.494 (2)	C62—C63	1.375 (3)
C4—C5	1.405 (2)	C43—H43	0.9300
C3—C30	1.426 (3)	C43—C44	1.398 (3)
C41—H41	0.9300	C46—H46	0.9300
C41—C40	1.373 (2)	C44—H44	0.9300
C40—C47	1.419 (3)	C63—H63	0.9300
C5—H5	0.9300	C63—C64	1.370 (3)
C61—H61	0.9300	C64—H64	0.9300
C6—N1—C2	124.23 (14)	C46—C49—C48	118.80 (15)
C6—N1—H1	119.1 (13)	C46—C49—C45	122.42 (17)
C2—N1—H1	116.7 (13)	C48—C42—H42	119.8
N1—C6—C60	118.17 (14)	C43—C42—C48	120.48 (18)
N1—C6—C5	119.25 (16)	C43—C42—H42	119.8
C5—C6—C60	122.49 (15)	C60—C65—H65	120.1
O2—C2—N1	120.53 (15)	C64—C65—C60	119.83 (18)
O2—C2—C3	123.93 (16)	C64—C65—H65	120.1
N1—C2—C3	115.50 (15)	C40—C47—H47	119.4
C49—C48—C41	119.03 (16)	C46—C47—C40	121.16 (17)
C42—C48—C41	121.83 (16)	C46—C47—H47	119.4
C42—C48—C49	119.14 (15)	C49—C45—H45	119.8
C61—C60—C6	120.54 (16)	C44—C45—C49	120.49 (18)
C61—C60—C65	119.16 (17)	C44—C45—H45	119.8
C65—C60—C6	120.18 (16)	C61—C62—H62	120.0
C3—C4—C40	123.54 (15)	C63—C62—C61	119.97 (19)
C3—C4—C5	117.71 (14)	C63—C62—H62	120.0
C5—C4—C40	118.54 (15)	N31—C30—C3	178.4 (2)
C4—C3—C2	121.73 (15)	C42—C43—H43	119.8
C4—C3—C30	123.54 (15)	C42—C43—C44	120.30 (18)
C30—C3—C2	114.38 (15)	C44—C43—H43	119.8
C48—C41—H41	119.4	C49—C46—H46	119.5
C40—C41—C48	121.29 (16)	C47—C46—C49	121.03 (17)
C40—C41—H41	119.4	C47—C46—H46	119.5
C41—C40—C4	123.20 (15)	C45—C44—C43	120.75 (17)
C41—C40—C47	118.67 (15)	C45—C44—H44	119.6
C47—C40—C4	118.11 (15)	C43—C44—H44	119.6
C6—C5—C4	121.42 (16)	C62—C63—H63	119.9
C6—C5—H5	119.3	C64—C63—C62	120.21 (19)
C4—C5—H5	119.3	C64—C63—H63	119.9
C60—C61—H61	119.9	C65—C64—H64	119.7
C62—C61—C60	120.29 (18)	C63—C64—C65	120.52 (19)
C62—C61—H61	119.9	C63—C64—H64	119.7
C48—C49—C45	118.78 (17)
O2—C2—C3—C4	176.33 (17)	C41—C48—C49—C46	−1.4 (3)
O2—C2—C3—C30	3.0 (3)	C41—C48—C42—C43	−178.05 (17)
N1—C6—C60—C61	135.08 (17)	C41—C40—C47—C46	−0.7 (3)
N1—C6—C60—C65	−49.1 (2)	C40—C4—C3—C2	−170.35 (16)
N1—C6—C5—C4	2.1 (3)	C40—C4—C3—C30	2.4 (3)
N1—C2—C3—C4	−1.4 (2)	C40—C4—C5—C6	170.28 (16)
N1—C2—C3—C30	−174.79 (15)	C40—C47—C46—C49	0.8 (3)
C6—N1—C2—O2	−179.26 (16)	C5—C6—C60—C61	−48.6 (2)
C6—N1—C2—C3	−1.4 (2)	C5—C6—C60—C65	127.28 (19)
C6—C60—C61—C62	176.01 (17)	C5—C4—C3—C2	4.3 (2)
C6—C60—C65—C64	−174.71 (18)	C5—C4—C3—C30	177.09 (17)
C2—N1—C6—C60	177.59 (15)	C5—C4—C40—C41	148.18 (17)
C2—N1—C6—C5	1.1 (3)	C5—C4—C40—C47	−32.9 (2)
C48—C41—C40—C4	178.35 (16)	C61—C60—C65—C64	1.2 (3)
C48—C41—C40—C47	−0.5 (3)	C61—C62—C63—C64	1.4 (3)
C48—C49—C45—C44	−0.3 (3)	C49—C48—C41—C40	1.6 (3)
C48—C49—C46—C47	0.3 (3)	C49—C48—C42—C43	2.2 (3)
C48—C42—C43—C44	−0.6 (3)	C49—C45—C44—C43	2.0 (3)
C60—C6—C5—C4	−174.25 (16)	C42—C48—C41—C40	−178.13 (16)
C60—C61—C62—C63	−1.4 (3)	C42—C48—C49—C45	−1.8 (3)
C60—C65—C64—C63	−1.2 (3)	C42—C48—C49—C46	178.30 (17)
C4—C40—C47—C46	−179.62 (18)	C42—C43—C44—C45	−1.6 (3)
C3—C4—C40—C41	−37.2 (3)	C65—C60—C61—C62	0.1 (3)
C3—C4—C40—C47	141.73 (18)	C45—C49—C46—C47	−179.63 (19)
C3—C4—C5—C6	−4.7 (3)	C62—C63—C64—C65	−0.1 (3)
C41—C48—C49—C45	178.47 (16)	C46—C49—C45—C44	179.63 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.90 (2)	1.91 (2)	2.8096 (18)	172.8 (19)

Symmetry code: (i) −x+2, −y+1, −z+1.