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The centrosymmetric title compound, C16H12N2O2, is composed of two pyridin-2(1H)-one rings linked to the para-positions of a central benzene ring via C—N bonds. Inter­molecular C—H...O inter­actions produce infinite mol­ecular sheets made up of R22(8) and R22(14) rings. C—H...π(arene) inter­actions inter­connect the sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041274/om2057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041274/om2057Isup2.hkl
Contains datablock I

CCDC reference: 628044

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.111
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.797 0.991 Tmin(prime) and Tmax expected: 0.966 0.991 RR(prime) = 0.825 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
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 2 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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXL97 and PLATON.

1-{4-[2-Oxopyridin-1(2H)-yl]phenyl}pyridin-2(1H)-one top
Crystal data top
C16H12N2O2Z = 1
Mr = 264.28F(000) = 138
Triclinic, P1Dx = 1.444 Mg m3
Hall symbol: -P 1Melting point = 591.3–592.9 K
a = 5.8911 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.7028 (13) ÅCell parameters from 1306 reflections
c = 8.8707 (18) Åθ = 2.5–30.6°
α = 76.50 (3)°µ = 0.10 mm1
β = 71.33 (3)°T = 295 K
γ = 67.44 (3)°Plate, colourless
V = 303.99 (13) Å30.35 × 0.19 × 0.09 mm
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
1396 independent reflections
Radiation source: fine-focus sealed tube1064 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 77
Tmin = 0.797, Tmax = 0.991k = 88
4208 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0464P)2 + 0.076P]
where P = (Fo2 + 2Fc2)/3
1396 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

Experimental. RF = 0.20 (CH2Cl2/MeOH = 95:5). 1H-NMR (400 MHz, DMSO) δ 7.67 (d, J = 7.2 Hz, 2H), 7.53 (s, 4H), 7.51 (t, J = 7.2 Hz, 2H), 6.49 (d, J = 9.2 Hz, 2H), 6.32 (t, J = 6.8 Hz, 2H). 13C-NMR (100 MHz, DMSO) δ 161.8 (C=O), 141.4, 140.9, 139.5, 128.1, 121.3, 106.5.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6355 (2)0.28659 (17)0.69593 (14)0.0490 (3)
N10.8798 (2)0.39546 (18)0.79369 (14)0.0323 (3)
C10.7194 (3)0.4297 (2)0.69500 (17)0.0346 (3)
C20.6677 (3)0.6387 (2)0.59727 (18)0.0398 (4)
H20.56050.67270.53070.048*
C30.7703 (3)0.7861 (2)0.59958 (19)0.0430 (4)
H30.73110.91980.53590.052*
C40.9366 (3)0.7402 (2)0.69739 (19)0.0433 (4)
H41.00840.84170.69800.052*
C50.9889 (3)0.5458 (2)0.78984 (18)0.0380 (4)
H51.10150.51250.85260.046*
C60.9406 (3)0.1917 (2)0.89808 (16)0.0316 (3)
C71.1930 (3)0.0645 (2)0.88668 (17)0.0358 (3)
H71.32180.10820.81090.043*
C80.7472 (3)0.1287 (2)1.01094 (17)0.0357 (4)
H80.57830.21531.01820.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0586 (7)0.0464 (6)0.0562 (8)0.0299 (6)0.0295 (6)0.0095 (5)
N10.0371 (6)0.0287 (6)0.0322 (6)0.0137 (5)0.0113 (5)0.0019 (5)
C10.0337 (7)0.0336 (7)0.0366 (8)0.0122 (6)0.0110 (6)0.0003 (6)
C20.0397 (8)0.0363 (8)0.0394 (8)0.0093 (6)0.0151 (7)0.0035 (6)
C30.0477 (9)0.0287 (7)0.0436 (9)0.0098 (6)0.0098 (7)0.0039 (6)
C40.0538 (9)0.0337 (8)0.0455 (9)0.0221 (7)0.0101 (7)0.0018 (6)
C50.0445 (8)0.0374 (8)0.0370 (8)0.0192 (7)0.0120 (7)0.0023 (6)
C60.0369 (7)0.0292 (7)0.0306 (7)0.0138 (6)0.0121 (6)0.0023 (5)
C70.0340 (7)0.0375 (8)0.0356 (8)0.0169 (6)0.0072 (6)0.0019 (6)
C80.0312 (7)0.0354 (7)0.0377 (8)0.0105 (6)0.0094 (6)0.0000 (6)
Geometric parameters (Å, º) top
O1—C11.2334 (17)C4—C51.349 (2)
N1—C11.4078 (18)C4—H40.9300
N1—C51.3770 (17)C5—H50.9300
N1—C61.4482 (17)C6—C71.385 (2)
C1—C21.4430 (19)C6—C81.386 (2)
C2—C31.348 (2)C7—C8i1.3900 (19)
C2—H20.9300C7—H70.9300
C3—C41.413 (2)C8—H80.9300
C3—H30.9300
C5—N1—C1122.18 (11)C5—C4—H4120.8
C5—N1—C6118.79 (11)C3—C4—H4120.8
C1—N1—C6118.98 (11)C4—C5—N1121.74 (13)
O1—C1—N1120.32 (12)C4—C5—H5119.1
O1—C1—C2125.01 (13)N1—C5—H5119.1
N1—C1—C2114.67 (12)C7—C6—C8120.66 (12)
C3—C2—C1121.94 (14)C7—C6—N1119.39 (12)
C3—C2—H2119.0C8—C6—N1119.92 (12)
C1—C2—H2119.0C6—C7—C8i119.66 (13)
C2—C3—C4120.95 (13)C6—C7—H7120.2
C2—C3—H3119.5C8i—C7—H7120.2
C4—C3—H3119.5C6—C8—H8120.2
C5—C4—C3118.42 (14)
C5—N1—C1—O1176.33 (14)C6—N1—C5—C4178.80 (14)
C6—N1—C1—O11.1 (2)C5—N1—C6—C753.79 (18)
C5—N1—C1—C23.4 (2)C1—N1—C6—C7123.74 (15)
C6—N1—C1—C2179.18 (13)C5—N1—C6—C8124.49 (15)
O1—C1—C2—C3178.52 (16)C1—N1—C6—C857.98 (18)
N1—C1—C2—C31.2 (2)C8—C6—C7—C8i0.3 (2)
C1—C2—C3—C40.8 (3)N1—C6—C7—C8i178.53 (13)
C2—C3—C4—C50.6 (2)C7—C6—C8—C7i0.3 (2)
C3—C4—C5—N11.6 (2)N1—C6—C8—C7i178.52 (13)
C1—N1—C5—C43.8 (2)
Symmetry code: (i) x+2, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1ii0.932.543.448 (2)166
C7—H7···O1iii0.932.413.294 (2)159
C8—H8···Cg1iv0.933.023.6814 (18)129
C4—H4···Cg2v0.933.083.7015 (19)125
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z+2; (v) x+2, y+1, z+2.
 

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