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The structure of the title compound, C15H14Cl2N2O2, comprises an essentially flat mol­ecule [dihedral angle of 3.64 (9)° between the two aromatic rings] with an intramolecular hydrogen-bonding interaction from the amine N-H group to the phenoxy O atom. Molecules are arranged in lamellar sheets parallel to the (110) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016350/cf6274sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016350/cf6274Isup2.hkl
Contains datablock I

CCDC reference: 222862

Key indicators

  • Single-crystal X-ray study
  • T = 220 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.109
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ............ 24.95 Deg. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ..... 0.96
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ..... 0.70 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ..... ?
2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

A search of the April 2003 release of the Cambridge Structural Database (Allen, 2002) reveals that there are eight structures based on N-(4,6-dimethylpyridin-2-yl)carboxamide, all published by one research group. These structures are N-(4,6-dimethylpyridin-2-yl)-2-(3-nitrophenyl)acetamide (Rodier et al., 1986), N-(4,6-dimethylpyridin-2-yl)-2-(4-nitrophenyl)propionamide (Rodier, Robert & Le Bautet, 1990), (E)—N-(4,6-dimethylpyridin-2-yl)-3-phenylpropenamide hemihydrate (Rodier, Robert-Piessard & Le Baut, 1990), N-(4,6-dimethylpyridin-2-yl)-2-furamide (Rodier et al., 1991), N-(4,6-dimethylpyridin-2-yl)-2-thiophenecarboxamide (Rodier, Cense et al., 1992), N-(4,6-dimethylpyridin-2-yl)(1-methylindol-2-yl)carboxamide (Rodier, Robert & Le Baut, 1992), N-(4,6-dimethylpyridin-2-yl)-2-(3-nitrophenyl)acetamide (Rodier et al., 1993) and N-(4,6-dimethylpyridin-2-yl)-5-methylpyrazine-2-carboxamide (Rodier et al., 1994). In a series of studies on the syntheses of additional derivatives of N-(4,6-dimethylpyridin-2-yl)carboxamide and also N-(4,6-dimethylpyrimidin-2-yl)carboxamide as potential anti-inflammatory agents, we prepared the title compound, (I), and its structure is reported here.

The structure of (I) comprises an essentially flat molecule (Fig. 1) with an intramolecular hydrogen-bonding interaction from the amine N—H group to the phenoxy O atom (Table 1). Molecules of (I) are arranged in lamellar sheets parallel to the (110) plane. The dihedral angle between the substituted phenyl and pyridyl rings is 3.64 (9)°.

Experimental top

Four molar equivalents of oxalyl chloride (2.29 g, 18.1 mmol) were added dropwise to a stirred solution of (2,4-dichlorophenoxy)acetic acid (1.0 g, 4.5 mmol) and a catalytic amount of dry pyridine (dried over KOH) in 20 ml dry dichloromethane (dried over molecular sieves). After stirring for 30 min, the solvent was removed under reduced pressure, yielding a yellow solution of (2,4-dichlorophenoxy)acetic chloride. This solution was then added dropwise to a stirred solution of 2-amino-4,6-dimethylpyridine (0.55 g, 4.5 mmol) and triethylamine (0.46 g, 4.5 mmol) in 20 ml dry dichloromethane. After 30 min, the solution was filtered and the solvent removed under reduced pressure, yielding a white powder. The product was purified using column chromatography (SiO2) and collected in the eluted ethyl acetate fraction after initial chloroform elutions. The solid product was further washed with 30 ml cold ethanol to afford 0.82 g of (I) (81%); m.p. 435–436 K; 1H NMR (CDCl3, 250 MHz): δ (p.p.m.) 2.33 (s, 3H, CH3), 2.42 (s, 3H, CH3), 4.62 (s, 2H, CH2), 6.77 (s, 1H, Ar—H), 6.89 (d, J 8.8, 1H, Ar—H), 7.33 (d, J 8.8, 1H, Ar—H), 7.41 (d, J 2.5, 1H, py—H), 7.87 (s, 1H, py—H), 8.89 (bs, 1H, NH); m/z 325 (MH+, 100%), 327 (MH+, 75%). Crystals suitable for X-ray diffraction studies were grown from ethyl acetate.

Refinement top

All H atoms were included in the refinement at calculated positions, as riding atoms, with N—H set to 0.87 Å and C—H set to 0.97 (CH3), 0.98 (CH2) or 0.94 Å (Ar—H); the isotropic displacement parameters were set at 1.25 times Ueq of the carrier atom.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1990); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability displacement ellipsoids.
2-(2,4-Dichlorophenoxy)-N-(4,6-dimethylpyridin-2-yl)acetamide top
Crystal data top
C15H14Cl2N2O2F(000) = 336
Mr = 325.18Dx = 1.413 Mg m3
Triclinic, P1Melting point: 435 K
a = 7.445 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.790 (6) ÅCell parameters from 22 reflections
c = 12.549 (7) Åθ = 15–16°
α = 89.28 (4)°µ = 0.43 mm1
β = 87.08 (5)°T = 220 K
γ = 68.74 (4)°Prism, colourless
V = 764.4 (9) Å30.70 × 0.47 × 0.38 mm
Z = 2
Data collection top
Stoe Stadi-4
diffractometer
Rint = 0.019
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.9°
Graphite monochromatorh = 88
ω/θ scansk = 1010
3678 measured reflectionsl = 014
2570 independent reflections3 standard reflections every 60 min
2032 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.062P)2 + 0.1634P]
where P = (Fo2 + 2Fc2)/3
2570 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C15H14Cl2N2O2γ = 68.74 (4)°
Mr = 325.18V = 764.4 (9) Å3
Triclinic, P1Z = 2
a = 7.445 (5) ÅMo Kα radiation
b = 8.790 (6) ŵ = 0.43 mm1
c = 12.549 (7) ÅT = 220 K
α = 89.28 (4)°0.70 × 0.47 × 0.38 mm
β = 87.08 (5)°
Data collection top
Stoe Stadi-4
diffractometer
Rint = 0.019
3678 measured reflections3 standard reflections every 60 min
2570 independent reflections intensity decay: 3%
2032 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
2570 reflectionsΔρmin = 0.30 e Å3
196 parameters
Special details top

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.0686 (0.0066) x + 5.4322 (0.0078) y − 0.8081 (0.0113) z = 7.1858 (0.0137)

* 0.0021 (0.0015) C1 * 0.0030 (0.0015) C2 * −0.0054 (0.0015) C3 * 0.0026 (0.0015) C4 * 0.0025 (0.0016) C5 * −0.0049 (0.0016) C6

Rms deviation of fitted atoms = 0.0036

6.9084 (0.0065) x + 5.8475 (0.0075) y − 0.9470 (0.0110) z = 7.1684 (0.0180)

Angle to previous plane (with approximate e.s.d.) = 3.64 (0.09)

* −0.0066 (0.0014) C12 * 0.0035 (0.0013) N13 * 0.0025 (0.0015) C14 * −0.0053 (0.0015) C15 * 0.0024 (0.0015) C16 * 0.0034 (0.0014) C17

Rms deviation of fitted atoms = 0.0042

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7680 (3)0.4768 (3)0.02870 (16)0.0350 (5)
C20.6560 (3)0.6291 (3)0.07107 (16)0.0379 (5)
Cl20.64800 (11)0.65788 (8)0.20750 (5)0.0635 (2)
C30.5510 (3)0.7546 (3)0.00706 (17)0.0400 (5)
H30.47450.85660.03670.050*
C40.5601 (3)0.7281 (3)0.10125 (17)0.0383 (5)
Cl40.42869 (10)0.88715 (8)0.18233 (5)0.0579 (2)
C50.6701 (3)0.5784 (3)0.14543 (17)0.0446 (6)
H50.67490.56200.21960.056*
C60.7729 (3)0.4529 (3)0.08047 (17)0.0427 (5)
H60.84690.35040.11040.060 (8)*
O70.8631 (2)0.36317 (18)0.10017 (11)0.0456 (4)
C80.9777 (3)0.2030 (3)0.06473 (17)0.0384 (5)
H811.07730.20720.01200.047 (6)*
H820.89680.15270.03090.047 (7)*
C91.0706 (3)0.1029 (3)0.15923 (17)0.0365 (5)
O101.1621 (3)0.04317 (19)0.14712 (13)0.0533 (5)
N111.0458 (3)0.1869 (2)0.25137 (13)0.0365 (4)
H110.97970.29100.24730.046*
C121.1110 (3)0.1314 (3)0.35346 (16)0.0338 (5)
N131.0269 (3)0.2445 (2)0.42800 (14)0.0381 (4)
C141.0738 (3)0.2054 (3)0.52910 (17)0.0410 (5)
C151.2042 (3)0.0543 (3)0.55577 (18)0.0455 (6)
H151.23260.03050.62760.048 (7)*
C161.2938 (3)0.0629 (3)0.47775 (18)0.0418 (5)
C171.2448 (3)0.0218 (3)0.37256 (17)0.0385 (5)
H171.30110.09630.31640.048*
C180.9729 (4)0.3355 (3)0.6116 (2)0.0597 (7)
H1811.00430.29130.68230.075*
H1820.83450.37200.60460.075*
H1831.01500.42710.60080.075*
C191.4333 (4)0.2283 (3)0.5054 (2)0.0548 (6)
H1911.36310.29270.53750.069*
H1921.52260.21690.55560.069*
H1931.50440.28260.44120.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0377 (12)0.0342 (11)0.0317 (11)0.0107 (10)0.0064 (9)0.0035 (9)
C20.0423 (12)0.0407 (12)0.0286 (11)0.0120 (10)0.0058 (9)0.0008 (9)
Cl20.0839 (5)0.0523 (4)0.0327 (3)0.0032 (3)0.0157 (3)0.0074 (3)
C30.0392 (12)0.0355 (12)0.0400 (12)0.0068 (10)0.0069 (10)0.0019 (10)
C40.0365 (12)0.0418 (12)0.0376 (11)0.0147 (10)0.0106 (9)0.0116 (10)
Cl40.0620 (4)0.0567 (4)0.0493 (4)0.0134 (3)0.0180 (3)0.0224 (3)
C50.0527 (14)0.0517 (14)0.0292 (11)0.0184 (12)0.0046 (10)0.0042 (10)
C60.0503 (14)0.0395 (12)0.0333 (11)0.0098 (11)0.0038 (10)0.0020 (10)
O70.0599 (10)0.0331 (8)0.0318 (8)0.0011 (8)0.0127 (7)0.0004 (6)
C80.0412 (12)0.0345 (11)0.0337 (11)0.0066 (10)0.0028 (9)0.0038 (9)
C90.0348 (11)0.0374 (12)0.0345 (11)0.0093 (10)0.0047 (9)0.0023 (9)
O100.0609 (11)0.0364 (9)0.0464 (9)0.0038 (8)0.0153 (8)0.0064 (7)
N110.0429 (10)0.0301 (9)0.0319 (9)0.0073 (8)0.0051 (8)0.0014 (7)
C120.0355 (11)0.0372 (11)0.0311 (10)0.0159 (10)0.0044 (9)0.0039 (9)
N130.0440 (11)0.0389 (10)0.0338 (10)0.0177 (9)0.0051 (8)0.0010 (8)
C140.0462 (13)0.0473 (13)0.0349 (11)0.0228 (11)0.0073 (10)0.0021 (10)
C150.0486 (14)0.0593 (15)0.0343 (12)0.0255 (13)0.0098 (10)0.0073 (11)
C160.0349 (12)0.0463 (13)0.0467 (13)0.0172 (11)0.0084 (10)0.0135 (11)
C170.0367 (12)0.0399 (12)0.0370 (12)0.0115 (10)0.0031 (9)0.0029 (9)
C180.0782 (19)0.0644 (17)0.0391 (13)0.0281 (16)0.0070 (13)0.0090 (12)
C190.0472 (15)0.0581 (16)0.0546 (15)0.0128 (13)0.0153 (12)0.0198 (12)
Geometric parameters (Å, º) top
C1—O71.354 (3)N11—C121.411 (3)
C1—C61.385 (3)N11—H110.87
C1—C21.391 (3)C12—N131.330 (3)
C2—C31.374 (3)C12—C171.381 (3)
C2—Cl21.729 (2)N13—C141.340 (3)
C3—C41.376 (3)C14—C151.380 (3)
C3—H30.94C14—C181.507 (3)
C4—C51.379 (3)C15—C161.387 (3)
C4—Cl41.738 (2)C15—H150.94
C5—C61.377 (3)C16—C171.396 (3)
C5—H50.94C16—C191.497 (3)
C6—H60.94C17—H170.94
O7—C81.419 (3)C18—H1810.97
C8—C91.508 (3)C18—H1820.97
C8—H810.98C18—H1830.97
C8—H820.98C19—H1910.97
C9—O101.223 (3)C19—H1920.97
C9—N111.348 (3)C19—H1930.97
O7—C1—C6125.7 (2)C12—N11—H11115.2
O7—C1—C2115.67 (19)N13—C12—C17124.8 (2)
C6—C1—C2118.7 (2)N13—C12—N11111.47 (19)
C3—C2—C1121.4 (2)C17—C12—N11123.75 (19)
C3—C2—Cl2120.06 (17)C12—N13—C14117.3 (2)
C1—C2—Cl2118.56 (18)N13—C14—C15121.9 (2)
C2—C3—C4118.8 (2)N13—C14—C18115.8 (2)
C2—C3—H3120.6C15—C14—C18122.3 (2)
C4—C3—H3120.6C14—C15—C16120.7 (2)
C5—C4—C3121.1 (2)C14—C15—H15119.6
C5—C4—Cl4120.12 (18)C16—C15—H15119.6
C3—C4—Cl4118.79 (18)C15—C16—C17117.3 (2)
C6—C5—C4119.7 (2)C15—C16—C19121.5 (2)
C6—C5—H5120.2C17—C16—C19121.3 (2)
C4—C5—H5120.2C12—C17—C16118.0 (2)
C5—C6—C1120.4 (2)C12—C17—H17121.0
C5—C6—H6119.8C16—C17—H17121.0
C1—C6—H6119.8C14—C18—H181109.5
C1—O7—C8119.76 (17)C14—C18—H182109.5
O7—C8—C9108.97 (17)H181—C18—H182109.5
O7—C8—H81109.9C14—C18—H183109.5
C9—C8—H81109.9H181—C18—H183109.5
O7—C8—H82109.9H182—C18—H183109.5
C9—C8—H82109.9C16—C19—H191109.5
H81—C8—H82108.3C16—C19—H192109.5
O10—C9—N11125.6 (2)H191—C19—H192109.5
O10—C9—C8119.18 (19)C16—C19—H193109.5
N11—C9—C8115.19 (18)H191—C19—H193109.5
C9—N11—C12129.69 (18)H192—C19—H193109.5
C9—N11—H11115.2
O7—C1—C2—C3179.43 (19)O7—C8—C9—N117.2 (3)
C6—C1—C2—C30.1 (3)O10—C9—N11—C121.7 (4)
O7—C1—C2—Cl20.3 (3)C8—C9—N11—C12179.32 (19)
C6—C1—C2—Cl2179.28 (17)C9—N11—C12—N13168.0 (2)
C1—C2—C3—C40.8 (3)C9—N11—C12—C1711.7 (3)
Cl2—C2—C3—C4179.97 (16)C17—C12—N13—C141.1 (3)
C2—C3—C4—C50.8 (3)N11—C12—N13—C14178.64 (17)
C2—C3—C4—Cl4179.59 (16)C12—N13—C14—C150.2 (3)
C3—C4—C5—C60.0 (3)C12—N13—C14—C18178.9 (2)
Cl4—C4—C5—C6179.65 (17)N13—C14—C15—C160.7 (3)
C4—C5—C6—C10.7 (4)C18—C14—C15—C16179.7 (2)
O7—C1—C6—C5179.9 (2)C14—C15—C16—C170.7 (3)
C2—C1—C6—C50.6 (3)C14—C15—C16—C19179.0 (2)
C6—C1—O7—C80.9 (3)N13—C12—C17—C161.1 (3)
C2—C1—O7—C8178.58 (19)N11—C12—C17—C16178.60 (19)
C1—O7—C8—C9178.64 (18)C15—C16—C17—C120.2 (3)
O7—C8—C9—O10173.7 (2)C19—C16—C17—C12178.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O70.872.072.552 (3)114

Experimental details

Crystal data
Chemical formulaC15H14Cl2N2O2
Mr325.18
Crystal system, space groupTriclinic, P1
Temperature (K)220
a, b, c (Å)7.445 (5), 8.790 (6), 12.549 (7)
α, β, γ (°)89.28 (4), 87.08 (5), 68.74 (4)
V3)764.4 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.70 × 0.47 × 0.38
Data collection
DiffractometerStoe Stadi-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3678, 2570, 2032
Rint0.019
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.109, 1.05
No. of reflections2570
No. of parameters196
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.30

Computer programs: DIF4 (Stoe & Cie, 1990), DIF4, REDU4 (Stoe & Cie, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O70.872.072.552 (3)114
 

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