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

Tu, N.; Long, S.

doi:10.1107/S241431462300603X

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

Crystals of the title compound, C₁₂H₈Cl₂N₂O₂, were obtained by slow evaporation of an ethanolic solution. An intramolecular _amideN—H

O=C_lactam hydrogen bond is observed. In the crystal, two molecules pair up to form a centrosymmetric lactam–lactam dimers (LLD) by N—H

O=C hydrogen bonds, whereas the O=C_amide group of the molecule does not participate in hydrogen bonding.

Keywords: crystal structure; highly twisted conformation; lactam–lactam dimer; N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462300603X/wm4188sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S241431462300603X/wm4188Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S241431462300603X/wm4188Isup3.cml Supplementary material

CCDC reference: 2280201

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.004 Å
R factor = 0.077
wR factor = 0.210
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter Within Range of ...      3.250 Sigma
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT601_ALERT_2_C Unit Cell Contains Solvent Accessible VOIDS of .         42 Ang   3
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         39 Report
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.76Ang From O2      .       0.49 eA-3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.17 Report
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl2      ..Cl2      .       3.32 Ang.
                                                 1-x,2-y,-z  =      2_675 Check
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        84% Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          4 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

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

Crystal data top

C₁₂H₈Cl₂N₂O₂	Z = 2
M_r = 283.10	F(000) = 288
Triclinic, P1	D_x = 1.524 Mg m⁻³
a = 7.3730 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.0091 (6) Å	Cell parameters from 4779 reflections
c = 10.8545 (6) Å	θ = 4.1–76.2°
α = 97.296 (6)°	µ = 4.71 mm⁻¹
β = 95.228 (6)°	T = 297 K
γ = 102.149 (7)°	Block, clear light colourless
V = 616.93 (8) Å³	0.21 × 0.18 × 0.17 mm

Data collection top

XtaLAB Synergy R, DW system, HyPix diffractometer	2135 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	1943 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.073
Detector resolution: 10.0000 pixels mm^-1	θ_max = 66.6°, θ_min = 4.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −9→8
T_min = 0.140, T_max = 1.000	l = −12→12
5370 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.077	w = 1/[σ²(F_o²) + (0.173P)² + 0.0514P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.210	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.74 e Å⁻³
2135 reflections	Δρ_min = −0.61 e Å⁻³
168 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.013 (4)
Primary atom site location: dual

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.09456 (12)	0.25172 (11)	0.21934 (9)	0.0689 (4)
Cl2	0.33699 (11)	0.84435 (8)	0.03740 (7)	0.0606 (4)
O1	0.0726 (3)	0.8647 (3)	0.38156 (19)	0.0573 (6)
O2	0.4804 (3)	0.5753 (3)	0.32403 (18)	0.0601 (7)
N1	0.2015 (3)	0.9462 (3)	0.5833 (2)	0.0451 (6)
N2	0.2180 (3)	0.6370 (3)	0.2380 (2)	0.0449 (6)
H2	0.128318	0.688602	0.249405	0.054*
C1	0.1941 (3)	0.8550 (3)	0.4661 (2)	0.0416 (6)
C2	0.3370 (3)	0.7567 (3)	0.4535 (2)	0.0394 (6)
C3	0.4628 (4)	0.7595 (4)	0.5538 (3)	0.0458 (7)
H3	0.553867	0.695703	0.544571	0.055*
C4	0.4597 (4)	0.8558 (4)	0.6713 (3)	0.0498 (7)
H4	0.546583	0.856661	0.739168	0.060*
C5	0.3257 (4)	0.9469 (4)	0.6815 (3)	0.0478 (7)
H5	0.319516	1.011107	0.758020	0.057*
C6	0.3521 (4)	0.6494 (3)	0.3331 (2)	0.0414 (6)
C7	0.2203 (3)	0.5413 (3)	0.1196 (2)	0.0390 (6)
C8	0.1698 (3)	0.3609 (3)	0.0998 (3)	0.0441 (6)
C9	0.1746 (4)	0.2670 (4)	−0.0165 (3)	0.0533 (8)
H9	0.139775	0.146970	−0.028567	0.064*
C10	0.2312 (4)	0.3524 (4)	−0.1133 (3)	0.0542 (8)
H10	0.236139	0.289553	−0.190562	0.065*
C11	0.2804 (4)	0.5292 (4)	−0.0971 (3)	0.0484 (7)
H11	0.317890	0.586835	−0.162878	0.058*
C12	0.2733 (3)	0.6204 (3)	0.0189 (2)	0.0405 (6)
H1	0.118 (5)	0.999 (4)	0.589 (3)	0.047 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0707 (6)	0.0764 (6)	0.0693 (7)	0.0185 (4)	0.0188 (4)	0.0360 (5)
Cl2	0.0779 (6)	0.0474 (5)	0.0549 (6)	0.0110 (4)	0.0063 (4)	0.0078 (4)
O1	0.0613 (12)	0.0848 (15)	0.0359 (10)	0.0487 (11)	0.0014 (9)	−0.0050 (10)
O2	0.0628 (12)	0.0913 (15)	0.0394 (11)	0.0527 (11)	0.0088 (9)	−0.0018 (10)
N1	0.0521 (13)	0.0599 (13)	0.0319 (12)	0.0322 (10)	0.0106 (10)	0.0022 (10)
N2	0.0500 (12)	0.0643 (14)	0.0291 (12)	0.0346 (10)	0.0091 (9)	−0.0001 (10)
C1	0.0457 (13)	0.0540 (14)	0.0328 (13)	0.0253 (11)	0.0125 (11)	0.0055 (11)
C2	0.0446 (13)	0.0509 (14)	0.0308 (13)	0.0230 (10)	0.0130 (10)	0.0098 (11)
C3	0.0519 (14)	0.0557 (15)	0.0370 (14)	0.0278 (11)	0.0069 (11)	0.0063 (12)
C4	0.0600 (16)	0.0652 (17)	0.0310 (13)	0.0317 (13)	0.0034 (12)	0.0042 (12)
C5	0.0566 (15)	0.0610 (16)	0.0304 (13)	0.0234 (12)	0.0099 (11)	0.0032 (11)
C6	0.0472 (13)	0.0548 (14)	0.0311 (13)	0.0251 (10)	0.0142 (11)	0.0096 (11)
C7	0.0380 (12)	0.0509 (14)	0.0319 (13)	0.0213 (10)	0.0071 (10)	−0.0005 (11)
C8	0.0444 (13)	0.0512 (14)	0.0446 (15)	0.0223 (10)	0.0121 (11)	0.0119 (12)
C9	0.0537 (15)	0.0443 (13)	0.0626 (19)	0.0219 (11)	0.0054 (13)	−0.0062 (13)
C10	0.0576 (15)	0.0658 (17)	0.0430 (16)	0.0290 (13)	0.0135 (13)	−0.0082 (14)
C11	0.0531 (14)	0.0656 (17)	0.0315 (13)	0.0227 (12)	0.0139 (11)	0.0040 (12)
C12	0.0421 (12)	0.0461 (13)	0.0357 (13)	0.0158 (9)	0.0088 (10)	0.0029 (11)

Geometric parameters (Å, º) top

Cl1—C8	1.724 (3)	C3—C4	1.409 (4)
Cl2—C12	1.736 (3)	C4—H4	0.9300
O1—C1	1.244 (3)	C4—C5	1.350 (4)
O2—C6	1.223 (3)	C5—H5	0.9300
N1—C1	1.375 (4)	C7—C8	1.398 (4)
N1—C5	1.339 (4)	C7—C12	1.378 (4)
N1—H1	0.82 (4)	C8—C9	1.392 (4)
N2—H2	0.8600	C9—H9	0.9300
N2—C6	1.341 (3)	C9—C10	1.374 (5)
N2—C7	1.414 (3)	C10—H10	0.9300
C1—C2	1.448 (3)	C10—C11	1.369 (5)
C2—C3	1.359 (4)	C11—H11	0.9300
C2—C6	1.497 (3)	C11—C12	1.384 (4)
C3—H3	0.9300

C1—N1—H1	113 (2)	O2—C6—N2	122.4 (2)
C5—N1—C1	125.1 (2)	O2—C6—C2	120.6 (2)
C5—N1—H1	122 (2)	N2—C6—C2	117.0 (2)
C6—N2—H2	119.2	C8—C7—N2	121.1 (2)
C6—N2—C7	121.6 (2)	C12—C7—N2	122.0 (2)
C7—N2—H2	119.2	C12—C7—C8	116.9 (2)
O1—C1—N1	119.5 (2)	C7—C8—Cl1	119.9 (2)
O1—C1—C2	126.0 (2)	C9—C8—Cl1	119.1 (2)
N1—C1—C2	114.5 (2)	C9—C8—C7	121.0 (3)
C1—C2—C6	122.5 (2)	C8—C9—H9	120.2
C3—C2—C1	119.7 (2)	C10—C9—C8	119.7 (3)
C3—C2—C6	117.8 (2)	C10—C9—H9	120.2
C2—C3—H3	119.0	C9—C10—H10	119.6
C2—C3—C4	122.1 (2)	C11—C10—C9	120.7 (3)
C4—C3—H3	119.0	C11—C10—H10	119.6
C3—C4—H4	121.3	C10—C11—H11	120.6
C5—C4—C3	117.5 (3)	C10—C11—C12	118.8 (3)
C5—C4—H4	121.3	C12—C11—H11	120.6
N1—C5—C4	121.1 (3)	C7—C12—Cl2	119.05 (19)
N1—C5—H5	119.4	C7—C12—C11	122.9 (2)
C4—C5—H5	119.4	C11—C12—Cl2	118.0 (2)

Cl1—C8—C9—C10	178.9 (2)	C5—N1—C1—O1	−179.7 (3)
O1—C1—C2—C3	179.2 (3)	C5—N1—C1—C2	−0.9 (4)
O1—C1—C2—C6	−1.2 (4)	C6—N2—C7—C8	76.0 (3)
N1—C1—C2—C3	0.5 (4)	C6—N2—C7—C12	−103.5 (3)
N1—C1—C2—C6	−179.9 (2)	C6—C2—C3—C4	−179.7 (2)
N2—C7—C8—Cl1	2.5 (3)	C7—N2—C6—O2	−2.1 (4)
N2—C7—C8—C9	−179.1 (2)	C7—N2—C6—C2	178.9 (2)
N2—C7—C12—Cl2	−0.6 (3)	C7—C8—C9—C10	0.5 (4)
N2—C7—C12—C11	178.6 (2)	C8—C7—C12—Cl2	179.79 (17)
C1—N1—C5—C4	0.9 (5)	C8—C7—C12—C11	−1.0 (4)
C1—C2—C3—C4	−0.1 (4)	C8—C9—C10—C11	−0.9 (5)
C1—C2—C6—O2	176.1 (3)	C9—C10—C11—C12	0.4 (4)
C1—C2—C6—N2	−4.8 (4)	C10—C11—C12—Cl2	179.8 (2)
C2—C3—C4—C5	0.0 (5)	C10—C11—C12—C7	0.5 (4)
C3—C2—C6—O2	−4.3 (4)	C12—C7—C8—Cl1	−177.95 (18)
C3—C2—C6—N2	174.8 (2)	C12—C7—C8—C9	0.4 (4)
C3—C4—C5—N1	−0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.01	2.703 (3)	137
N1—H1···O1ⁱ	0.82 (4)	1.97 (4)	2.794 (3)	175 (3)

Symmetry code: (i) −x, −y+2, −z+1.

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

Supporting information

Key indicators

checkCIF/PLATON results

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