In the crystal structure of the title compound, C18H14N4O2·C2H6OS, the N,N′-di-2-pyridylbenzene-1,3-dicarboxamide molecule is non-planar, the two pyridine rings being twisted with respect to the benzene ring by 30.0 (2) and 27.5 (1)°. The two imino groups are hydrogen bonded with the dimethyl sulfoxide solvent molecule.
Supporting information
CCDC reference: 625039
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.113
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S1
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C6 .. 2.97 Ang.
0 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
N,
N'-Di-2-pyridylbenzene-1,3-dicarboxamide dimethyl sulfoxide
solvate
top
Crystal data top
C18H14N4O2·C2H6OS | F(000) = 832 |
Mr = 396.46 | Dx = 1.320 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 2169 reflections |
a = 10.4852 (17) Å | θ = 2.5–22.8° |
b = 16.274 (3) Å | µ = 0.19 mm−1 |
c = 12.101 (2) Å | T = 294 K |
β = 104.921 (3)° | Block, colorless |
V = 1995.3 (6) Å3 | 0.26 × 0.22 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2168 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 26.4°, θmin = 2.1° |
φ and ω scans | h = −13→8 |
11180 measured reflections | k = −20→18 |
4059 independent reflections | l = −14→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.1524P] where P = (Fo2 + 2Fc2)/3 |
4059 reflections | (Δ/σ)max = 0.003 |
255 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.26052 (18) | −0.09689 (10) | 0.69710 (16) | 0.0740 (6) | |
O2 | 0.70398 (18) | −0.07877 (11) | 0.92410 (17) | 0.0766 (6) | |
N1 | 1.13368 (18) | 0.01768 (11) | 0.65177 (16) | 0.0509 (5) | |
H1 | 1.0677 | 0.0431 | 0.6659 | 0.061* | |
N2 | 1.1305 (2) | 0.12392 (12) | 0.52971 (18) | 0.0614 (6) | |
N3 | 0.73018 (18) | 0.02666 (11) | 0.80966 (15) | 0.0495 (5) | |
H3 | 0.7819 | 0.0447 | 0.7703 | 0.059* | |
N4 | 0.6081 (2) | 0.13795 (13) | 0.73469 (18) | 0.0616 (6) | |
C1 | 1.1007 (2) | −0.07314 (12) | 0.80021 (19) | 0.0445 (6) | |
C2 | 1.1674 (2) | −0.11796 (14) | 0.8962 (2) | 0.0547 (6) | |
H2 | 1.2541 | −0.1344 | 0.9033 | 0.066* | |
C3 | 1.1060 (3) | −0.13794 (14) | 0.9802 (2) | 0.0589 (7) | |
H3A | 1.1512 | −0.1681 | 1.0435 | 0.071* | |
C4 | 0.9780 (3) | −0.11354 (13) | 0.9711 (2) | 0.0545 (6) | |
H4 | 0.9371 | −0.1270 | 1.0285 | 0.065* | |
C5 | 0.9094 (2) | −0.06874 (12) | 0.87611 (19) | 0.0457 (6) | |
C6 | 0.9715 (2) | −0.04967 (12) | 0.7914 (2) | 0.0456 (6) | |
H6 | 0.9256 | −0.0205 | 0.7274 | 0.055* | |
C7 | 1.1724 (2) | −0.05267 (14) | 0.7121 (2) | 0.0511 (6) | |
C8 | 1.1891 (2) | 0.05334 (14) | 0.5694 (2) | 0.0491 (6) | |
C9 | 1.2931 (2) | 0.02114 (17) | 0.5335 (2) | 0.0650 (7) | |
H9 | 1.3305 | −0.0290 | 0.5615 | 0.078* | |
C10 | 1.3400 (3) | 0.0649 (2) | 0.4555 (2) | 0.0759 (8) | |
H10 | 1.4102 | 0.0444 | 0.4300 | 0.091* | |
C11 | 1.2841 (3) | 0.1382 (2) | 0.4151 (2) | 0.0759 (8) | |
H11 | 1.3158 | 0.1691 | 0.3632 | 0.091* | |
C12 | 1.1798 (3) | 0.16454 (17) | 0.4537 (2) | 0.0738 (8) | |
H12 | 1.1402 | 0.2140 | 0.4254 | 0.089* | |
C13 | 0.7718 (2) | −0.04168 (14) | 0.8729 (2) | 0.0512 (6) | |
C14 | 0.6139 (2) | 0.07180 (14) | 0.80006 (19) | 0.0485 (6) | |
C15 | 0.5168 (3) | 0.05268 (16) | 0.8547 (2) | 0.0643 (7) | |
H15 | 0.5220 | 0.0052 | 0.8984 | 0.077* | |
C16 | 0.4120 (3) | 0.1064 (2) | 0.8425 (3) | 0.0745 (8) | |
H16 | 0.3459 | 0.0958 | 0.8792 | 0.089* | |
C17 | 0.4057 (3) | 0.17505 (19) | 0.7764 (3) | 0.0728 (8) | |
H17 | 0.3362 | 0.2120 | 0.7674 | 0.087* | |
C18 | 0.5045 (3) | 0.18772 (17) | 0.7242 (3) | 0.0727 (8) | |
H18 | 0.4995 | 0.2341 | 0.6783 | 0.087* | |
S1 | 0.88030 (6) | 0.21222 (4) | 0.69602 (6) | 0.0541 (2) | |
O3 | 0.92858 (16) | 0.12631 (9) | 0.72870 (15) | 0.0635 (5) | |
C19 | 0.8019 (3) | 0.20987 (17) | 0.5494 (2) | 0.0813 (9) | |
H19A | 0.8590 | 0.1842 | 0.5090 | 0.122* | |
H19B | 0.7826 | 0.2650 | 0.5218 | 0.122* | |
H19C | 0.7213 | 0.1791 | 0.5370 | 0.122* | |
C20 | 1.0216 (3) | 0.27017 (16) | 0.6902 (3) | 0.0871 (10) | |
H20A | 1.0782 | 0.2762 | 0.7659 | 0.131* | |
H20B | 0.9947 | 0.3235 | 0.6587 | 0.131* | |
H20C | 1.0684 | 0.2423 | 0.6428 | 0.131* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0754 (13) | 0.0673 (12) | 0.0870 (14) | 0.0310 (10) | 0.0345 (11) | 0.0128 (10) |
O2 | 0.0807 (13) | 0.0609 (12) | 0.1022 (15) | −0.0036 (9) | 0.0489 (12) | 0.0251 (10) |
N1 | 0.0492 (12) | 0.0447 (11) | 0.0637 (14) | 0.0071 (9) | 0.0235 (10) | 0.0078 (10) |
N2 | 0.0733 (15) | 0.0537 (13) | 0.0614 (14) | 0.0038 (11) | 0.0247 (12) | 0.0077 (11) |
N3 | 0.0514 (12) | 0.0497 (12) | 0.0531 (12) | 0.0023 (10) | 0.0236 (10) | 0.0071 (9) |
N4 | 0.0536 (14) | 0.0618 (14) | 0.0719 (15) | 0.0088 (11) | 0.0205 (11) | 0.0149 (12) |
C1 | 0.0502 (15) | 0.0338 (11) | 0.0471 (14) | 0.0003 (11) | 0.0081 (12) | −0.0014 (10) |
C2 | 0.0556 (16) | 0.0455 (14) | 0.0579 (16) | 0.0079 (12) | 0.0053 (13) | 0.0008 (12) |
C3 | 0.078 (2) | 0.0469 (15) | 0.0454 (15) | 0.0035 (14) | 0.0035 (14) | 0.0062 (12) |
C4 | 0.0750 (19) | 0.0425 (13) | 0.0472 (15) | −0.0055 (13) | 0.0177 (14) | 0.0035 (11) |
C5 | 0.0552 (16) | 0.0324 (12) | 0.0489 (14) | −0.0034 (11) | 0.0128 (12) | 0.0002 (10) |
C6 | 0.0511 (15) | 0.0342 (12) | 0.0500 (14) | 0.0003 (11) | 0.0105 (12) | 0.0026 (10) |
C7 | 0.0506 (15) | 0.0436 (14) | 0.0581 (16) | 0.0053 (12) | 0.0119 (13) | −0.0019 (12) |
C8 | 0.0493 (15) | 0.0476 (14) | 0.0507 (15) | −0.0037 (12) | 0.0132 (12) | −0.0020 (12) |
C9 | 0.0612 (18) | 0.0683 (18) | 0.0723 (19) | 0.0025 (14) | 0.0296 (15) | −0.0001 (14) |
C10 | 0.071 (2) | 0.094 (2) | 0.070 (2) | −0.0084 (17) | 0.0320 (16) | −0.0089 (18) |
C11 | 0.086 (2) | 0.085 (2) | 0.0639 (19) | −0.0220 (18) | 0.0315 (17) | −0.0003 (17) |
C12 | 0.095 (2) | 0.0615 (18) | 0.0672 (19) | −0.0028 (16) | 0.0242 (18) | 0.0099 (15) |
C13 | 0.0610 (16) | 0.0407 (13) | 0.0540 (15) | −0.0070 (12) | 0.0189 (13) | 0.0017 (11) |
C14 | 0.0478 (15) | 0.0518 (14) | 0.0463 (14) | −0.0050 (12) | 0.0128 (12) | −0.0025 (12) |
C15 | 0.0599 (17) | 0.0697 (18) | 0.0695 (18) | −0.0023 (14) | 0.0279 (14) | 0.0050 (14) |
C16 | 0.0530 (18) | 0.102 (2) | 0.075 (2) | −0.0023 (17) | 0.0295 (15) | −0.0078 (18) |
C17 | 0.0545 (19) | 0.084 (2) | 0.079 (2) | 0.0121 (15) | 0.0146 (16) | −0.0035 (17) |
C18 | 0.0581 (19) | 0.077 (2) | 0.083 (2) | 0.0165 (15) | 0.0176 (16) | 0.0179 (16) |
S1 | 0.0600 (4) | 0.0428 (3) | 0.0655 (4) | −0.0009 (3) | 0.0268 (3) | −0.0050 (3) |
O3 | 0.0706 (12) | 0.0492 (10) | 0.0781 (12) | 0.0087 (8) | 0.0328 (9) | 0.0153 (9) |
C19 | 0.106 (2) | 0.0652 (19) | 0.0642 (19) | 0.0008 (16) | 0.0071 (17) | 0.0044 (15) |
C20 | 0.0698 (19) | 0.0524 (17) | 0.143 (3) | −0.0091 (14) | 0.0353 (19) | −0.0083 (18) |
Geometric parameters (Å, º) top
O1—C7 | 1.221 (3) | C9—C10 | 1.371 (4) |
O2—C13 | 1.216 (3) | C9—H9 | 0.9300 |
N1—C7 | 1.362 (3) | C10—C11 | 1.364 (4) |
N1—C8 | 1.403 (3) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—C12 | 1.365 (4) |
N2—C8 | 1.332 (3) | C11—H11 | 0.9300 |
N2—C12 | 1.340 (3) | C12—H12 | 0.9300 |
N3—C13 | 1.357 (3) | C14—C15 | 1.385 (3) |
N3—C14 | 1.402 (3) | C15—C16 | 1.382 (4) |
N3—H3 | 0.8600 | C15—H15 | 0.9300 |
N4—C14 | 1.328 (3) | C16—C17 | 1.366 (4) |
N4—C18 | 1.334 (3) | C16—H16 | 0.9300 |
C1—C6 | 1.384 (3) | C17—C18 | 1.360 (4) |
C1—C2 | 1.397 (3) | C17—H17 | 0.9300 |
C1—C7 | 1.492 (3) | C18—H18 | 0.9300 |
C2—C3 | 1.375 (3) | S1—O3 | 1.5048 (16) |
C2—H2 | 0.9300 | S1—C19 | 1.753 (3) |
C3—C4 | 1.377 (3) | S1—C20 | 1.773 (3) |
C3—H3A | 0.9300 | C19—H19A | 0.9600 |
C4—C5 | 1.395 (3) | C19—H19B | 0.9600 |
C4—H4 | 0.9300 | C19—H19C | 0.9600 |
C5—C6 | 1.384 (3) | C20—H20A | 0.9600 |
C5—C13 | 1.500 (3) | C20—H20B | 0.9600 |
C6—H6 | 0.9300 | C20—H20C | 0.9600 |
C8—C9 | 1.377 (3) | | |
| | | |
C7—N1—C8 | 127.4 (2) | C12—C11—H11 | 121.3 |
C7—N1—H1 | 116.3 | C10—C11—H11 | 121.3 |
C8—N1—H1 | 116.3 | N2—C12—C11 | 124.4 (3) |
C8—N2—C12 | 116.7 (2) | N2—C12—H12 | 117.8 |
C13—N3—C14 | 128.49 (19) | C11—C12—H12 | 117.8 |
C13—N3—H3 | 115.8 | O2—C13—N3 | 123.3 (2) |
C14—N3—H3 | 115.8 | O2—C13—C5 | 121.7 (2) |
C14—N4—C18 | 117.4 (2) | N3—C13—C5 | 115.0 (2) |
C6—C1—C2 | 118.6 (2) | N4—C14—C15 | 122.7 (2) |
C6—C1—C7 | 123.1 (2) | N4—C14—N3 | 112.3 (2) |
C2—C1—C7 | 118.3 (2) | C15—C14—N3 | 125.0 (2) |
C3—C2—C1 | 120.5 (2) | C16—C15—C14 | 118.0 (3) |
C3—C2—H2 | 119.7 | C16—C15—H15 | 121.0 |
C1—C2—H2 | 119.7 | C14—C15—H15 | 121.0 |
C2—C3—C4 | 120.4 (2) | C17—C16—C15 | 119.8 (3) |
C2—C3—H3A | 119.8 | C17—C16—H16 | 120.1 |
C4—C3—H3A | 119.8 | C15—C16—H16 | 120.1 |
C3—C4—C5 | 120.1 (2) | C18—C17—C16 | 117.9 (3) |
C3—C4—H4 | 120.0 | C18—C17—H17 | 121.0 |
C5—C4—H4 | 120.0 | C16—C17—H17 | 121.0 |
C6—C5—C4 | 119.2 (2) | N4—C18—C17 | 124.2 (3) |
C6—C5—C13 | 123.2 (2) | N4—C18—H18 | 117.9 |
C4—C5—C13 | 117.6 (2) | C17—C18—H18 | 117.9 |
C5—C6—C1 | 121.2 (2) | O3—S1—C19 | 106.50 (12) |
C5—C6—H6 | 119.4 | O3—S1—C20 | 106.06 (12) |
C1—C6—H6 | 119.4 | C19—S1—C20 | 98.62 (15) |
O1—C7—N1 | 123.3 (2) | S1—C19—H19A | 109.5 |
O1—C7—C1 | 121.0 (2) | S1—C19—H19B | 109.5 |
N1—C7—C1 | 115.8 (2) | H19A—C19—H19B | 109.5 |
N2—C8—C9 | 123.0 (2) | S1—C19—H19C | 109.5 |
N2—C8—N1 | 112.1 (2) | H19A—C19—H19C | 109.5 |
C9—C8—N1 | 125.0 (2) | H19B—C19—H19C | 109.5 |
C10—C9—C8 | 118.2 (3) | S1—C20—H20A | 109.5 |
C10—C9—H9 | 120.9 | S1—C20—H20B | 109.5 |
C8—C9—H9 | 120.9 | H20A—C20—H20B | 109.5 |
C11—C10—C9 | 120.2 (3) | S1—C20—H20C | 109.5 |
C11—C10—H10 | 119.9 | H20A—C20—H20C | 109.5 |
C9—C10—H10 | 119.9 | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 117.4 (3) | | |
| | | |
C6—C1—C2—C3 | −0.2 (3) | N1—C8—C9—C10 | −177.4 (2) |
C7—C1—C2—C3 | 179.6 (2) | C8—C9—C10—C11 | −0.1 (4) |
C1—C2—C3—C4 | −0.4 (4) | C9—C10—C11—C12 | −1.2 (4) |
C2—C3—C4—C5 | 0.4 (3) | C8—N2—C12—C11 | 0.2 (4) |
C3—C4—C5—C6 | 0.3 (3) | C10—C11—C12—N2 | 1.1 (4) |
C3—C4—C5—C13 | −178.1 (2) | C14—N3—C13—O2 | 7.3 (4) |
C4—C5—C6—C1 | −1.0 (3) | C14—N3—C13—C5 | −172.4 (2) |
C13—C5—C6—C1 | 177.36 (19) | C6—C5—C13—O2 | 155.7 (2) |
C2—C1—C6—C5 | 1.0 (3) | C4—C5—C13—O2 | −25.9 (3) |
C7—C1—C6—C5 | −178.88 (19) | C6—C5—C13—N3 | −24.6 (3) |
C8—N1—C7—O1 | −3.4 (4) | C4—C5—C13—N3 | 153.8 (2) |
C8—N1—C7—C1 | 176.07 (19) | C18—N4—C14—C15 | 1.1 (4) |
C6—C1—C7—O1 | −151.8 (2) | C18—N4—C14—N3 | −176.7 (2) |
C2—C1—C7—O1 | 28.4 (3) | C13—N3—C14—N4 | 176.9 (2) |
C6—C1—C7—N1 | 28.7 (3) | C13—N3—C14—C15 | −1.0 (4) |
C2—C1—C7—N1 | −151.1 (2) | N4—C14—C15—C16 | −1.8 (4) |
C12—N2—C8—C9 | −1.6 (4) | N3—C14—C15—C16 | 175.8 (2) |
C12—N2—C8—N1 | 177.4 (2) | C14—C15—C16—C17 | 1.1 (4) |
C7—N1—C8—N2 | −177.7 (2) | C15—C16—C17—C18 | 0.2 (4) |
C7—N1—C8—C9 | 1.3 (4) | C14—N4—C18—C17 | 0.3 (4) |
N2—C8—C9—C10 | 1.5 (4) | C16—C17—C18—N4 | −1.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.26 | 3.106 (3) | 168 |
N3—H3···O3 | 0.86 | 2.19 | 2.994 (3) | 156 |