Crystals of the title compound, C
12H
8Cl
2N
2O
2, 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.
Supporting information
CCDC reference: 2280201
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
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 |
Mr = 283.10 | F(000) = 288 |
Triclinic, P1 | Dx = 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 | Rint = 0.073 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 66.6°, θmin = 4.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −9→8 |
Tmin = 0.140, Tmax = 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(Fo2) + (0.173P)2 + 0.0514P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.210 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.74 e Å−3 |
2135 reflections | Δρmin = −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 | Uiso*/Ueq | |
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. |