N-(3-Chloro-2-methyl­phen­yl)-2-oxo-1,2-dihydro­pyridine-3-carboxamide

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.

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

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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

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Computing details

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

Crystal data

C13H11ClN2O2	F(000) = 272
Mr = 262.69	Dx = 1.560 Mg m^−3
Triclinic, P1	Melting point = 583–587 K
a = 7.1514 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5805 (2) Å	Cell parameters from 2523 reflections
c = 10.3268 (3) Å	θ = 1.0–27.5°
α = 87.8186 (14)°	µ = 0.34 mm^−1
β = 89.5131 (14)°	T = 90 K
γ = 89.2959 (13)°	Irregular block, colorless
V = 559.36 (3) Å^3	0.20 × 0.10 × 0.03 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.936, Tmax = 0.990	l = −13→13
4917 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.1363P] where P = (Fo^2 + 2Fc^2)/3
2560 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1630 (3)	0.2470 (3)	0.8461 (2)	0.0206 (5)
C2	0.1096 (3)	0.0802 (3)	0.8107 (2)	0.0210 (5)
H2	0.0807	−0.0090	0.8746	0.025*
C3	0.0995 (3)	0.0470 (3)	0.6804 (2)	0.0226 (5)
H3	0.0626	−0.0663	0.6546	0.027*
C4	0.1422 (3)	0.1761 (3)	0.5867 (2)	0.0214 (5)
H4	0.1350	0.1514	0.4974	0.026*
C5	0.1959 (3)	0.3427 (3)	0.6242 (2)	0.0183 (5)
C6	0.2075 (3)	0.3822 (3)	0.7570 (2)	0.0194 (5)
C7	0.2635 (3)	0.5632 (3)	0.7967 (2)	0.0225 (5)
H7A	0.2646	0.5663	0.8915	0.034*
H7B	0.1738	0.6512	0.7621	0.034*
H7C	0.3887	0.5898	0.7624	0.034*
C8	0.2402 (3)	0.4806 (3)	0.4021 (2)	0.0201 (5)
C9	0.3027 (3)	0.6516 (3)	0.33807 (19)	0.0179 (5)
C10	0.2890 (3)	0.6700 (3)	0.2056 (2)	0.0208 (5)
H10	0.2418	0.5749	0.1589	0.025*
C11	0.3426 (3)	0.8252 (3)	0.1372 (2)	0.0225 (5)
H11	0.3327	0.8355	0.0456	0.027*
C12	0.4086 (3)	0.9594 (3)	0.2054 (2)	0.0219 (5)
H12	0.4448	1.0661	0.1615	0.026*
C13	0.3757 (3)	0.7956 (3)	0.4089 (2)	0.0182 (5)
N1	0.2449 (2)	0.4785 (2)	0.53417 (16)	0.0192 (4)
H1	0.2842	0.5762	0.5679	0.023*
N2	0.4235 (2)	0.9428 (2)	0.33554 (16)	0.0202 (4)
H2A	0.4672	1.0333	0.3763	0.024*
O1	0.1894 (2)	0.35796 (19)	0.33714 (14)	0.0257 (4)
O2	0.3979 (2)	0.79608 (18)	0.52985 (13)	0.0211 (3)
Cl1	0.16995 (8)	0.28285 (7)	1.01212 (5)	0.02675 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0187 (12)	0.0211 (11)	0.0218 (11)	0.0024 (9)	0.0022 (9)	0.0004 (9)
C2	0.0189 (12)	0.0162 (11)	0.0278 (12)	0.0000 (9)	0.0014 (9)	0.0027 (9)
C3	0.0200 (12)	0.0150 (11)	0.0330 (13)	−0.0012 (9)	−0.0008 (9)	−0.0022 (9)
C4	0.0215 (12)	0.0186 (11)	0.0242 (12)	0.0005 (9)	−0.0004 (9)	−0.0024 (9)
C5	0.0162 (11)	0.0137 (11)	0.0247 (11)	0.0014 (8)	0.0015 (9)	0.0008 (8)
C6	0.0159 (11)	0.0166 (11)	0.0256 (12)	0.0031 (9)	0.0025 (9)	−0.0018 (9)
C7	0.0281 (13)	0.0172 (11)	0.0222 (11)	−0.0011 (9)	0.0019 (9)	−0.0014 (9)
C8	0.0166 (11)	0.0164 (11)	0.0274 (12)	0.0035 (9)	−0.0012 (9)	−0.0019 (9)
C9	0.0151 (11)	0.0162 (11)	0.0226 (11)	0.0009 (8)	0.0025 (8)	−0.0028 (8)
C10	0.0200 (12)	0.0197 (11)	0.0230 (11)	0.0013 (9)	0.0011 (9)	−0.0047 (9)
C11	0.0222 (12)	0.0262 (12)	0.0191 (11)	0.0002 (10)	−0.0002 (9)	0.0002 (9)
C12	0.0198 (12)	0.0228 (12)	0.0227 (11)	0.0002 (9)	0.0012 (9)	0.0036 (9)
C13	0.0157 (11)	0.0150 (11)	0.0238 (11)	0.0014 (8)	0.0026 (9)	0.0000 (9)
N1	0.0230 (10)	0.0141 (9)	0.0205 (9)	−0.0023 (7)	0.0014 (7)	−0.0018 (7)
N2	0.0239 (10)	0.0154 (9)	0.0215 (10)	−0.0023 (8)	0.0012 (8)	−0.0027 (7)
O1	0.0349 (10)	0.0190 (8)	0.0237 (8)	−0.0048 (7)	−0.0014 (7)	−0.0047 (7)
O2	0.0272 (9)	0.0173 (8)	0.0188 (8)	−0.0025 (6)	0.0011 (6)	−0.0021 (6)
Cl1	0.0378 (4)	0.0204 (3)	0.0219 (3)	−0.0018 (2)	0.0032 (2)	0.0003 (2)

Geometric parameters (Å, º)

C1—C2	1.388 (3)	C8—O1	1.227 (3)
C1—C6	1.389 (3)	C8—N1	1.364 (3)
C1—Cl1	1.748 (2)	C8—C9	1.504 (3)
C2—C3	1.381 (3)	C9—C10	1.374 (3)
C2—H2	0.9500	C9—C13	1.442 (3)
C3—C4	1.385 (3)	C10—C11	1.404 (3)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.394 (3)	C11—C12	1.351 (3)
C4—H4	0.9500	C11—H11	0.9500
C5—N1	1.407 (3)	C12—N2	1.350 (3)
C5—C6	1.418 (3)	C12—H12	0.9500
C6—C7	1.507 (3)	C13—O2	1.261 (2)
C7—H7A	0.9800	C13—N2	1.370 (3)
C7—H7B	0.9800	N1—H1	0.8800
C7—H7C	0.9800	N2—H2A	0.8800
C2—C1—C6	123.3 (2)	O1—C8—N1	125.2 (2)
C2—C1—Cl1	116.52 (16)	O1—C8—C9	120.82 (19)
C6—C1—Cl1	120.15 (17)	N1—C8—C9	113.99 (18)
C3—C2—C1	118.42 (19)	C10—C9—C13	118.95 (19)
C3—C2—H2	120.8	C10—C9—C8	117.85 (19)
C1—C2—H2	120.8	C13—C9—C8	123.20 (18)
C2—C3—C4	121.1 (2)	C9—C10—C11	122.0 (2)
C2—C3—H3	119.5	C9—C10—H10	119.0
C4—C3—H3	119.5	C11—C10—H10	119.0
C3—C4—C5	119.6 (2)	C12—C11—C10	118.1 (2)
C3—C4—H4	120.2	C12—C11—H11	120.9
C5—C4—H4	120.2	C10—C11—H11	120.9
C4—C5—N1	122.50 (19)	N2—C12—C11	120.5 (2)
C4—C5—C6	121.05 (19)	N2—C12—H12	119.8
N1—C5—C6	116.44 (18)	C11—C12—H12	119.8
C1—C6—C5	116.50 (19)	O2—C13—N2	118.73 (19)
C1—C6—C7	122.76 (19)	O2—C13—C9	125.70 (19)
C5—C6—C7	120.73 (18)	N2—C13—C9	115.56 (18)
C6—C7—H7A	109.5	C8—N1—C5	129.28 (18)
C6—C7—H7B	109.5	C8—N1—H1	115.4
H7A—C7—H7B	109.5	C5—N1—H1	115.4
C6—C7—H7C	109.5	C12—N2—C13	124.84 (19)
H7A—C7—H7C	109.5	C12—N2—H2A	117.6
H7B—C7—H7C	109.5	C13—N2—H2A	117.6
C6—C1—C2—C3	−0.2 (3)	N1—C8—C9—C13	4.8 (3)
Cl1—C1—C2—C3	179.03 (15)	C13—C9—C10—C11	−0.4 (3)
C1—C2—C3—C4	0.3 (3)	C8—C9—C10—C11	179.55 (18)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—N1	178.63 (19)	C10—C11—C12—N2	0.5 (3)
C3—C4—C5—C6	0.0 (3)	C10—C9—C13—O2	−179.12 (19)
C2—C1—C6—C5	0.0 (3)	C8—C9—C13—O2	0.9 (3)
Cl1—C1—C6—C5	−179.18 (14)	C10—C9—C13—N2	0.9 (3)
C2—C1—C6—C7	179.41 (19)	C8—C9—C13—N2	−179.09 (17)
Cl1—C1—C6—C7	0.2 (3)	O1—C8—N1—C5	0.2 (3)
C4—C5—C6—C1	0.1 (3)	C9—C8—N1—C5	179.65 (19)
N1—C5—C6—C1	−178.65 (18)	C4—C5—N1—C8	4.1 (3)
C4—C5—C6—C7	−179.31 (19)	C6—C5—N1—C8	−177.21 (18)
N1—C5—C6—C7	2.0 (3)	C11—C12—N2—C13	0.0 (3)
O1—C8—C9—C10	4.3 (3)	O2—C13—N2—C12	179.31 (18)
N1—C8—C9—C10	−175.16 (17)	C9—C13—N2—C12	−0.7 (3)
O1—C8—C9—C13	−175.69 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88	1.89	2.655 (2)	144
N2—H2A···O2^i	0.88	1.92	2.790 (2)	170

Symmetry code: (i) −x+1, −y+2, −z+1.