N-(3-Chloro-2-methyl­phen­yl)-6-oxo-1,6-di­hydro­pyridine-3-carboxamide

Tian, G.; Long, S.

doi:10.1107/S2414314623006028

N-(3-Chloro-2-methylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide

In the crystal structure of the title compound, C₁₃H₁₁ClN₂O₂, the molecules form a three-dimensional network based on two types of hydrogen bonds between NH groups and the carbonyl oxygen atoms and amides. The molecule is highly twisted, as evidenced by the dihedral angle between the 6-oxo-1,6-dihydropyridine and benzene rings [88.1 (2)°].

Keywords: crystal structure; 6-oxo-1,6-dihydropyridine; N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623006028/vm4061sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314623006028/vm4061Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314623006028/vm4061Isup3.cml Supplementary material

CCDC reference: 2280200

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 268 K
R factor = 0.060
wR factor = 0.184
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.13 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        163 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO 1.171.41.113a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.41.113a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.41.113a (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

N-(3-Chloro-2-methylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide top

Crystal data top

C₁₃H₁₁ClN₂O₂	Z = 2
M_r = 262.69	F(000) = 272
Triclinic, P1	D_x = 1.463 Mg m⁻³
a = 4.91237 (15) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.3037 (3) Å	Cell parameters from 4316 reflections
c = 12.5876 (3) Å	θ = 3.7–77.4°
α = 105.890 (2)°	µ = 2.81 mm⁻¹
β = 96.422 (2)°	T = 268 K
γ = 99.361 (2)°	Block, clear light colourless
V = 596.35 (3) Å³	0.11 × 0.05 × 0.04 mm

Data collection top

Rigaku Oxford Diffraction, Synergy Custom system, HyPix diffractometer	2362 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	2023 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.6°, θ_min = 3.7°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	k = −12→12
T_min = 0.482, T_max = 1.000	l = −15→11
5870 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.1286P)² + 0.0079P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2362 reflections	Δρ_max = 0.34 e Å⁻³
164 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints

Special details top

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.

Refinement. positions of H atoms at N1 and N2 were obtained from a difference Fourier map. Other H atoms were positioned geometrically with C—H = 0.93 Å (aromatic H) or 0.96 Å (methyl H), and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,O), where x=1.5 for methyl H, and x=1.2 for all other H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.70169 (15)	0.48597 (7)	0.88602 (4)	0.0568 (3)
O1	0.2394 (4)	0.10879 (18)	−0.04783 (12)	0.0467 (4)
O2	1.0545 (3)	0.2472 (2)	0.40507 (14)	0.0554 (5)
N1	0.2702 (4)	0.07879 (18)	0.12455 (14)	0.0351 (4)
H1	0.113762	0.020388	0.103199	0.042*
N2	0.6373 (4)	0.23089 (19)	0.46700 (13)	0.0367 (4)
H2	0.459644	0.221023	0.448300	0.044*
C1	0.3982 (4)	0.1067 (2)	0.23115 (16)	0.0344 (5)
H1A	0.313595	0.064270	0.278844	0.041*
C2	0.6488 (4)	0.1959 (2)	0.27013 (16)	0.0327 (4)
C3	0.7723 (5)	0.2563 (2)	0.19387 (18)	0.0387 (5)
H3	0.946826	0.314972	0.217320	0.046*
C4	0.6407 (5)	0.2301 (2)	0.08749 (18)	0.0403 (5)
H4	0.724547	0.272452	0.039606	0.048*
C5	0.3741 (4)	0.1379 (2)	0.04762 (16)	0.0338 (5)
C6	0.7985 (4)	0.2265 (2)	0.38631 (17)	0.0357 (5)
C7	0.7463 (4)	0.2510 (2)	0.58157 (16)	0.0330 (5)
C8	0.6758 (4)	0.3534 (2)	0.66538 (16)	0.0312 (4)
C9	0.7869 (5)	0.3634 (2)	0.77585 (17)	0.0369 (5)
C10	0.9636 (5)	0.2817 (3)	0.80184 (19)	0.0436 (5)
H10	1.034339	0.292535	0.876128	0.052*
C11	1.0340 (6)	0.1845 (3)	0.7173 (2)	0.0498 (6)
H11	1.156189	0.129966	0.733910	0.060*
C12	0.9234 (6)	0.1669 (2)	0.6069 (2)	0.0465 (6)
H12	0.967423	0.098984	0.549550	0.056*
C13	0.4974 (5)	0.4497 (2)	0.64070 (18)	0.0413 (5)
H13A	0.614874	0.532952	0.638879	0.062*
H13B	0.384069	0.471175	0.697991	0.062*
H13C	0.378964	0.406824	0.569413	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0737 (5)	0.0721 (5)	0.0188 (4)	0.0169 (3)	0.0033 (3)	0.0046 (3)
O1	0.0527 (10)	0.0628 (10)	0.0219 (8)	0.0063 (7)	−0.0090 (7)	0.0172 (7)
O2	0.0327 (9)	0.1011 (14)	0.0257 (9)	0.0141 (8)	−0.0021 (6)	0.0103 (9)
N1	0.0348 (9)	0.0473 (9)	0.0185 (9)	0.0040 (7)	−0.0040 (6)	0.0080 (7)
N2	0.0337 (9)	0.0570 (10)	0.0151 (9)	0.0098 (7)	−0.0028 (6)	0.0060 (7)
C1	0.0374 (11)	0.0466 (10)	0.0172 (10)	0.0085 (8)	0.0000 (8)	0.0078 (8)
C2	0.0349 (10)	0.0440 (10)	0.0158 (9)	0.0105 (8)	−0.0012 (7)	0.0037 (8)
C3	0.0354 (11)	0.0483 (11)	0.0284 (11)	0.0051 (8)	0.0008 (8)	0.0087 (9)
C4	0.0455 (12)	0.0502 (11)	0.0258 (11)	0.0050 (9)	0.0024 (9)	0.0162 (9)
C5	0.0400 (11)	0.0406 (10)	0.0211 (10)	0.0116 (8)	−0.0009 (8)	0.0101 (8)
C6	0.0344 (11)	0.0491 (11)	0.0186 (10)	0.0098 (8)	−0.0036 (8)	0.0045 (8)
C7	0.0355 (10)	0.0430 (10)	0.0184 (10)	0.0052 (8)	−0.0026 (7)	0.0102 (8)
C8	0.0344 (10)	0.0409 (10)	0.0181 (10)	0.0031 (7)	0.0002 (7)	0.0125 (8)
C9	0.0455 (12)	0.0473 (11)	0.0155 (10)	0.0026 (8)	−0.0009 (8)	0.0116 (8)
C10	0.0500 (13)	0.0597 (13)	0.0229 (11)	0.0053 (10)	−0.0048 (9)	0.0227 (10)
C11	0.0577 (15)	0.0569 (13)	0.0415 (14)	0.0171 (11)	−0.0031 (11)	0.0269 (12)
C12	0.0582 (15)	0.0492 (12)	0.0333 (13)	0.0196 (10)	0.0010 (10)	0.0117 (10)
C13	0.0504 (13)	0.0490 (11)	0.0247 (11)	0.0157 (9)	−0.0013 (9)	0.0114 (9)

Geometric parameters (Å, º) top

Cl1—C9	1.743 (2)	C3—C4	1.355 (3)
O1—C5	1.238 (2)	C4—C5	1.434 (3)
O2—C6	1.225 (3)	C7—C8	1.391 (3)
N1—C1	1.349 (3)	C7—C12	1.394 (3)
N1—C5	1.379 (3)	C8—C9	1.406 (3)
N2—C6	1.351 (3)	C8—C13	1.497 (3)
N2—C7	1.427 (2)	C9—C10	1.376 (3)
C1—C2	1.360 (3)	C10—C11	1.366 (4)
C2—C3	1.418 (3)	C11—C12	1.387 (3)
C2—C6	1.487 (3)

C1—N1—C5	124.19 (18)	N2—C6—C2	116.39 (17)
C6—N2—C7	123.50 (17)	C8—C7—N2	119.96 (17)
N1—C1—C2	121.18 (19)	C8—C7—C12	121.34 (18)
C1—C2—C3	117.44 (18)	C12—C7—N2	118.70 (19)
C1—C2—C6	122.53 (18)	C7—C8—C9	116.00 (18)
C3—C2—C6	119.98 (18)	C7—C8—C13	122.62 (17)
C4—C3—C2	121.2 (2)	C9—C8—C13	121.36 (19)
C3—C4—C5	120.99 (19)	C8—C9—Cl1	118.95 (17)
O1—C5—N1	119.92 (19)	C10—C9—Cl1	117.88 (16)
O1—C5—C4	125.14 (19)	C10—C9—C8	123.2 (2)
N1—C5—C4	114.93 (17)	C11—C10—C9	119.3 (2)
O2—C6—N2	123.42 (19)	C10—C11—C12	120.1 (2)
O2—C6—C2	120.18 (19)	C11—C12—C7	120.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.93	2.793 (3)	177
N2—H2···O2ⁱⁱ	0.86	2.08	2.926 (3)	166

Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z.

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N-(3-Chloro-2-methyl­phen­yl)-6-oxo-1,6-di­hydro­pyridine-3-carboxamide

Supporting information

Key indicators

checkCIF/PLATON results

N-(3-Chloro-2-methylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide