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The title compound, C13H11ClN2O2, contains two aromatic rings linked by an amide group, and adopts a near-planar conformation. There are intra- and inter­molecular N—H...O hydrogen bonds, forming centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603488X/ob2055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603488X/ob2055Isup2.hkl
Contains datablock I

CCDC reference: 624942

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.112
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

N-(3-chloro-2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide top
Crystal data top
C13H11ClN2O2F(000) = 272
Mr = 262.69Dx = 1.560 Mg m3
Triclinic, P1Melting point = 583–587 K
a = 7.1514 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.5805 (2) ÅCell parameters from 2523 reflections
c = 10.3268 (3) Åθ = 1.0–27.5°
α = 87.8186 (14)°µ = 0.34 mm1
β = 89.5131 (14)°T = 90 K
γ = 89.2959 (13)°Irregular block, colorless
V = 559.36 (3) Å30.20 × 0.10 × 0.03 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
2560 independent reflections
Radiation source: fine-focus sealed tube1811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.0°
ω scansh = 99
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 99
Tmin = 0.936, Tmax = 0.990l = 1313
4917 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1363P]
where P = (Fo2 + 2Fc2)/3
2560 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. 1H NMR (DMSO-d6, 400 MHz) 12.75 (s, 1H), 12.22 (s, 1H), 8.48 (m, 1H), 8.24 (m, 1H), 7.84 (m, 1H), 7.22 (m, 2H), 6.60 (m, 1H), 2.38 (s, 3H),; 13C NMR (DMSO-d6, 400 MHz) 162.7, 161.7, 144.9, 140.4, 138.5, 133.6, 127.3, 125.6, 124.4, 120.0, 119.9, 107.0, 14.5; IR (KBr) 3445 (s), 3060 (w), 2970 (w), 1695 (s), 1628 (s), 1606 (s), 1579 (s); MS (EI) 264.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1630 (3)0.2470 (3)0.8461 (2)0.0206 (5)
C20.1096 (3)0.0802 (3)0.8107 (2)0.0210 (5)
H20.08070.00900.87460.025*
C30.0995 (3)0.0470 (3)0.6804 (2)0.0226 (5)
H30.06260.06630.65460.027*
C40.1422 (3)0.1761 (3)0.5867 (2)0.0214 (5)
H40.13500.15140.49740.026*
C50.1959 (3)0.3427 (3)0.6242 (2)0.0183 (5)
C60.2075 (3)0.3822 (3)0.7570 (2)0.0194 (5)
C70.2635 (3)0.5632 (3)0.7967 (2)0.0225 (5)
H7A0.26460.56630.89150.034*
H7B0.17380.65120.76210.034*
H7C0.38870.58980.76240.034*
C80.2402 (3)0.4806 (3)0.4021 (2)0.0201 (5)
C90.3027 (3)0.6516 (3)0.33807 (19)0.0179 (5)
C100.2890 (3)0.6700 (3)0.2056 (2)0.0208 (5)
H100.24180.57490.15890.025*
C110.3426 (3)0.8252 (3)0.1372 (2)0.0225 (5)
H110.33270.83550.04560.027*
C120.4086 (3)0.9594 (3)0.2054 (2)0.0219 (5)
H120.44481.06610.16150.026*
C130.3757 (3)0.7956 (3)0.4089 (2)0.0182 (5)
N10.2449 (2)0.4785 (2)0.53417 (16)0.0192 (4)
H10.28420.57620.56790.023*
N20.4235 (2)0.9428 (2)0.33554 (16)0.0202 (4)
H2A0.46721.03330.37630.024*
O10.1894 (2)0.35796 (19)0.33714 (14)0.0257 (4)
O20.3979 (2)0.79608 (18)0.52985 (13)0.0211 (3)
Cl10.16995 (8)0.28285 (7)1.01212 (5)0.02675 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0187 (12)0.0211 (11)0.0218 (11)0.0024 (9)0.0022 (9)0.0004 (9)
C20.0189 (12)0.0162 (11)0.0278 (12)0.0000 (9)0.0014 (9)0.0027 (9)
C30.0200 (12)0.0150 (11)0.0330 (13)0.0012 (9)0.0008 (9)0.0022 (9)
C40.0215 (12)0.0186 (11)0.0242 (12)0.0005 (9)0.0004 (9)0.0024 (9)
C50.0162 (11)0.0137 (11)0.0247 (11)0.0014 (8)0.0015 (9)0.0008 (8)
C60.0159 (11)0.0166 (11)0.0256 (12)0.0031 (9)0.0025 (9)0.0018 (9)
C70.0281 (13)0.0172 (11)0.0222 (11)0.0011 (9)0.0019 (9)0.0014 (9)
C80.0166 (11)0.0164 (11)0.0274 (12)0.0035 (9)0.0012 (9)0.0019 (9)
C90.0151 (11)0.0162 (11)0.0226 (11)0.0009 (8)0.0025 (8)0.0028 (8)
C100.0200 (12)0.0197 (11)0.0230 (11)0.0013 (9)0.0011 (9)0.0047 (9)
C110.0222 (12)0.0262 (12)0.0191 (11)0.0002 (10)0.0002 (9)0.0002 (9)
C120.0198 (12)0.0228 (12)0.0227 (11)0.0002 (9)0.0012 (9)0.0036 (9)
C130.0157 (11)0.0150 (11)0.0238 (11)0.0014 (8)0.0026 (9)0.0000 (9)
N10.0230 (10)0.0141 (9)0.0205 (9)0.0023 (7)0.0014 (7)0.0018 (7)
N20.0239 (10)0.0154 (9)0.0215 (10)0.0023 (8)0.0012 (8)0.0027 (7)
O10.0349 (10)0.0190 (8)0.0237 (8)0.0048 (7)0.0014 (7)0.0047 (7)
O20.0272 (9)0.0173 (8)0.0188 (8)0.0025 (6)0.0011 (6)0.0021 (6)
Cl10.0378 (4)0.0204 (3)0.0219 (3)0.0018 (2)0.0032 (2)0.0003 (2)
Geometric parameters (Å, º) top
C1—C21.388 (3)C8—O11.227 (3)
C1—C61.389 (3)C8—N11.364 (3)
C1—Cl11.748 (2)C8—C91.504 (3)
C2—C31.381 (3)C9—C101.374 (3)
C2—H20.9500C9—C131.442 (3)
C3—C41.385 (3)C10—C111.404 (3)
C3—H30.9500C10—H100.9500
C4—C51.394 (3)C11—C121.351 (3)
C4—H40.9500C11—H110.9500
C5—N11.407 (3)C12—N21.350 (3)
C5—C61.418 (3)C12—H120.9500
C6—C71.507 (3)C13—O21.261 (2)
C7—H7A0.9800C13—N21.370 (3)
C7—H7B0.9800N1—H10.8800
C7—H7C0.9800N2—H2A0.8800
C2—C1—C6123.3 (2)O1—C8—N1125.2 (2)
C2—C1—Cl1116.52 (16)O1—C8—C9120.82 (19)
C6—C1—Cl1120.15 (17)N1—C8—C9113.99 (18)
C3—C2—C1118.42 (19)C10—C9—C13118.95 (19)
C3—C2—H2120.8C10—C9—C8117.85 (19)
C1—C2—H2120.8C13—C9—C8123.20 (18)
C2—C3—C4121.1 (2)C9—C10—C11122.0 (2)
C2—C3—H3119.5C9—C10—H10119.0
C4—C3—H3119.5C11—C10—H10119.0
C3—C4—C5119.6 (2)C12—C11—C10118.1 (2)
C3—C4—H4120.2C12—C11—H11120.9
C5—C4—H4120.2C10—C11—H11120.9
C4—C5—N1122.50 (19)N2—C12—C11120.5 (2)
C4—C5—C6121.05 (19)N2—C12—H12119.8
N1—C5—C6116.44 (18)C11—C12—H12119.8
C1—C6—C5116.50 (19)O2—C13—N2118.73 (19)
C1—C6—C7122.76 (19)O2—C13—C9125.70 (19)
C5—C6—C7120.73 (18)N2—C13—C9115.56 (18)
C6—C7—H7A109.5C8—N1—C5129.28 (18)
C6—C7—H7B109.5C8—N1—H1115.4
H7A—C7—H7B109.5C5—N1—H1115.4
C6—C7—H7C109.5C12—N2—C13124.84 (19)
H7A—C7—H7C109.5C12—N2—H2A117.6
H7B—C7—H7C109.5C13—N2—H2A117.6
C6—C1—C2—C30.2 (3)N1—C8—C9—C134.8 (3)
Cl1—C1—C2—C3179.03 (15)C13—C9—C10—C110.4 (3)
C1—C2—C3—C40.3 (3)C8—C9—C10—C11179.55 (18)
C2—C3—C4—C50.2 (3)C9—C10—C11—C120.3 (3)
C3—C4—C5—N1178.63 (19)C10—C11—C12—N20.5 (3)
C3—C4—C5—C60.0 (3)C10—C9—C13—O2179.12 (19)
C2—C1—C6—C50.0 (3)C8—C9—C13—O20.9 (3)
Cl1—C1—C6—C5179.18 (14)C10—C9—C13—N20.9 (3)
C2—C1—C6—C7179.41 (19)C8—C9—C13—N2179.09 (17)
Cl1—C1—C6—C70.2 (3)O1—C8—N1—C50.2 (3)
C4—C5—C6—C10.1 (3)C9—C8—N1—C5179.65 (19)
N1—C5—C6—C1178.65 (18)C4—C5—N1—C84.1 (3)
C4—C5—C6—C7179.31 (19)C6—C5—N1—C8177.21 (18)
N1—C5—C6—C72.0 (3)C11—C12—N2—C130.0 (3)
O1—C8—C9—C104.3 (3)O2—C13—N2—C12179.31 (18)
N1—C8—C9—C10175.16 (17)C9—C13—N2—C120.7 (3)
O1—C8—C9—C13175.69 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.881.892.655 (2)144
N2—H2A···O2i0.881.922.790 (2)170
Symmetry code: (i) x+1, y+2, z+1.
 

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