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Crystals of the title compound, C12H8Cl2N2O2, were obtained by slow evaporation of an ethano­lic solution. An intra­molecular amideN—H...O=Clactam 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=Camide group of the mol­ecule does not participate in hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462300603X/wm4188sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431462300603X/wm4188Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S241431462300603X/wm4188Isup3.cml
Supplementary material

CCDC reference: 2280201

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.077
  • wR factor = 0.210
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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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
C12H8Cl2N2O2Z = 2
Mr = 283.10F(000) = 288
Triclinic, P1Dx = 1.524 Mg m3
a = 7.3730 (6) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.0091 (6) ÅCell parameters from 4779 reflections
c = 10.8545 (6) Åθ = 4.1–76.2°
α = 97.296 (6)°µ = 4.71 mm1
β = 95.228 (6)°T = 297 K
γ = 102.149 (7)°Block, clear light colourless
V = 616.93 (8) Å30.21 × 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 Source1943 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.073
Detector resolution: 10.0000 pixels mm-1θmax = 66.6°, θmin = 4.1°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2022)
k = 98
Tmin = 0.140, Tmax = 1.000l = 1212
5370 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.077 w = 1/[σ2(Fo2) + (0.173P)2 + 0.0514P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.210(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.74 e Å3
2135 reflectionsΔρmin = 0.61 e Å3
168 parametersExtinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
Cl10.09456 (12)0.25172 (11)0.21934 (9)0.0689 (4)
Cl20.33699 (11)0.84435 (8)0.03740 (7)0.0606 (4)
O10.0726 (3)0.8647 (3)0.38156 (19)0.0573 (6)
O20.4804 (3)0.5753 (3)0.32403 (18)0.0601 (7)
N10.2015 (3)0.9462 (3)0.5833 (2)0.0451 (6)
N20.2180 (3)0.6370 (3)0.2380 (2)0.0449 (6)
H20.1283180.6886020.2494050.054*
C10.1941 (3)0.8550 (3)0.4661 (2)0.0416 (6)
C20.3370 (3)0.7567 (3)0.4535 (2)0.0394 (6)
C30.4628 (4)0.7595 (4)0.5538 (3)0.0458 (7)
H30.5538670.6957030.5445710.055*
C40.4597 (4)0.8558 (4)0.6713 (3)0.0498 (7)
H40.5465830.8566610.7391680.060*
C50.3257 (4)0.9469 (4)0.6815 (3)0.0478 (7)
H50.3195161.0111070.7580200.057*
C60.3521 (4)0.6494 (3)0.3331 (2)0.0414 (6)
C70.2203 (3)0.5413 (3)0.1196 (2)0.0390 (6)
C80.1698 (3)0.3609 (3)0.0998 (3)0.0441 (6)
C90.1746 (4)0.2670 (4)0.0165 (3)0.0533 (8)
H90.1397750.1469700.0285670.064*
C100.2312 (4)0.3524 (4)0.1133 (3)0.0542 (8)
H100.2361390.2895530.1905620.065*
C110.2804 (4)0.5292 (4)0.0971 (3)0.0484 (7)
H110.3178900.5868350.1628780.058*
C120.2733 (3)0.6204 (3)0.0189 (2)0.0405 (6)
H10.118 (5)0.999 (4)0.589 (3)0.047 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0707 (6)0.0764 (6)0.0693 (7)0.0185 (4)0.0188 (4)0.0360 (5)
Cl20.0779 (6)0.0474 (5)0.0549 (6)0.0110 (4)0.0063 (4)0.0078 (4)
O10.0613 (12)0.0848 (15)0.0359 (10)0.0487 (11)0.0014 (9)0.0050 (10)
O20.0628 (12)0.0913 (15)0.0394 (11)0.0527 (11)0.0088 (9)0.0018 (10)
N10.0521 (13)0.0599 (13)0.0319 (12)0.0322 (10)0.0106 (10)0.0022 (10)
N20.0500 (12)0.0643 (14)0.0291 (12)0.0346 (10)0.0091 (9)0.0001 (10)
C10.0457 (13)0.0540 (14)0.0328 (13)0.0253 (11)0.0125 (11)0.0055 (11)
C20.0446 (13)0.0509 (14)0.0308 (13)0.0230 (10)0.0130 (10)0.0098 (11)
C30.0519 (14)0.0557 (15)0.0370 (14)0.0278 (11)0.0069 (11)0.0063 (12)
C40.0600 (16)0.0652 (17)0.0310 (13)0.0317 (13)0.0034 (12)0.0042 (12)
C50.0566 (15)0.0610 (16)0.0304 (13)0.0234 (12)0.0099 (11)0.0032 (11)
C60.0472 (13)0.0548 (14)0.0311 (13)0.0251 (10)0.0142 (11)0.0096 (11)
C70.0380 (12)0.0509 (14)0.0319 (13)0.0213 (10)0.0071 (10)0.0005 (11)
C80.0444 (13)0.0512 (14)0.0446 (15)0.0223 (10)0.0121 (11)0.0119 (12)
C90.0537 (15)0.0443 (13)0.0626 (19)0.0219 (11)0.0054 (13)0.0062 (13)
C100.0576 (15)0.0658 (17)0.0430 (16)0.0290 (13)0.0135 (13)0.0082 (14)
C110.0531 (14)0.0656 (17)0.0315 (13)0.0227 (12)0.0139 (11)0.0040 (12)
C120.0421 (12)0.0461 (13)0.0357 (13)0.0158 (9)0.0088 (10)0.0029 (11)
Geometric parameters (Å, º) top
Cl1—C81.724 (3)C3—C41.409 (4)
Cl2—C121.736 (3)C4—H40.9300
O1—C11.244 (3)C4—C51.350 (4)
O2—C61.223 (3)C5—H50.9300
N1—C11.375 (4)C7—C81.398 (4)
N1—C51.339 (4)C7—C121.378 (4)
N1—H10.82 (4)C8—C91.392 (4)
N2—H20.8600C9—H90.9300
N2—C61.341 (3)C9—C101.374 (5)
N2—C71.414 (3)C10—H100.9300
C1—C21.448 (3)C10—C111.369 (5)
C2—C31.359 (4)C11—H110.9300
C2—C61.497 (3)C11—C121.384 (4)
C3—H30.9300
C1—N1—H1113 (2)O2—C6—N2122.4 (2)
C5—N1—C1125.1 (2)O2—C6—C2120.6 (2)
C5—N1—H1122 (2)N2—C6—C2117.0 (2)
C6—N2—H2119.2C8—C7—N2121.1 (2)
C6—N2—C7121.6 (2)C12—C7—N2122.0 (2)
C7—N2—H2119.2C12—C7—C8116.9 (2)
O1—C1—N1119.5 (2)C7—C8—Cl1119.9 (2)
O1—C1—C2126.0 (2)C9—C8—Cl1119.1 (2)
N1—C1—C2114.5 (2)C9—C8—C7121.0 (3)
C1—C2—C6122.5 (2)C8—C9—H9120.2
C3—C2—C1119.7 (2)C10—C9—C8119.7 (3)
C3—C2—C6117.8 (2)C10—C9—H9120.2
C2—C3—H3119.0C9—C10—H10119.6
C2—C3—C4122.1 (2)C11—C10—C9120.7 (3)
C4—C3—H3119.0C11—C10—H10119.6
C3—C4—H4121.3C10—C11—H11120.6
C5—C4—C3117.5 (3)C10—C11—C12118.8 (3)
C5—C4—H4121.3C12—C11—H11120.6
N1—C5—C4121.1 (3)C7—C12—Cl2119.05 (19)
N1—C5—H5119.4C7—C12—C11122.9 (2)
C4—C5—H5119.4C11—C12—Cl2118.0 (2)
Cl1—C8—C9—C10178.9 (2)C5—N1—C1—O1179.7 (3)
O1—C1—C2—C3179.2 (3)C5—N1—C1—C20.9 (4)
O1—C1—C2—C61.2 (4)C6—N2—C7—C876.0 (3)
N1—C1—C2—C30.5 (4)C6—N2—C7—C12103.5 (3)
N1—C1—C2—C6179.9 (2)C6—C2—C3—C4179.7 (2)
N2—C7—C8—Cl12.5 (3)C7—N2—C6—O22.1 (4)
N2—C7—C8—C9179.1 (2)C7—N2—C6—C2178.9 (2)
N2—C7—C12—Cl20.6 (3)C7—C8—C9—C100.5 (4)
N2—C7—C12—C11178.6 (2)C8—C7—C12—Cl2179.79 (17)
C1—N1—C5—C40.9 (5)C8—C7—C12—C111.0 (4)
C1—C2—C3—C40.1 (4)C8—C9—C10—C110.9 (5)
C1—C2—C6—O2176.1 (3)C9—C10—C11—C120.4 (4)
C1—C2—C6—N24.8 (4)C10—C11—C12—Cl2179.8 (2)
C2—C3—C4—C50.0 (5)C10—C11—C12—C70.5 (4)
C3—C2—C6—O24.3 (4)C12—C7—C8—Cl1177.95 (18)
C3—C2—C6—N2174.8 (2)C12—C7—C8—C90.4 (4)
C3—C4—C5—N10.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.862.012.703 (3)137
N1—H1···O1i0.82 (4)1.97 (4)2.794 (3)175 (3)
Symmetry code: (i) x, y+2, z+1.
 

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