In the title compound, C
20H
16ClN
3O
2, the salicylaldehyde group makes dihedral angles of 73.93 (7) and 21.59 (13)° with the terminal chlorobenzene ring and the pyridine mean plane, respectively. Packing is stabilized by intermolecular N—H
O hydrogen bonds and weak, non-classical intermolecular C—H
O hydrogen bonds that link adjacent molecules into one-dimensional extended chains.
Supporting information
CCDC reference: 627654
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.004 Å
- R factor = 0.047
- wR factor = 0.138
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Crystal data top
C20H16ClN3O2 | F(000) = 1520 |
Mr = 365.81 | Dx = 1.329 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3671 reflections |
a = 10.212 (2) Å | θ = 2.3–21.9° |
b = 9.696 (2) Å | µ = 0.23 mm−1 |
c = 36.927 (8) Å | T = 294 K |
V = 3656.4 (13) Å3 | Block, colorless |
Z = 8 | 0.26 × 0.20 × 0.14 mm |
Data collection top
Bruker SMART APEX CCD area detector diffractometer | 3639 independent reflections |
Radiation source: fine-focus sealed tube | 2059 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 26.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→8 |
Tmin = 0.934, Tmax = 0.969 | k = −12→10 |
18729 measured reflections | l = −45→30 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0621P)2 + 0.9225P] where P = (Fo2 + 2Fc2)/3 |
3639 reflections | (Δ/σ)max = 0.001 |
235 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.22 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 >
2σ(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 | |
Cl1 | 0.58983 (10) | 1.05062 (9) | 0.31490 (2) | 0.0918 (4) | |
O1 | 0.57948 (19) | 0.53391 (17) | 0.42885 (4) | 0.0584 (5) | |
O2 | 0.20504 (19) | 0.05250 (16) | 0.35534 (5) | 0.0602 (5) | |
N1 | 0.3528 (2) | 0.23223 (19) | 0.39528 (5) | 0.0461 (5) | |
N2 | 0.2927 (2) | 0.26354 (18) | 0.36280 (5) | 0.0455 (5) | |
H2 | 0.3006 | 0.3454 | 0.3541 | 0.055* | |
N3 | 0.0525 (3) | 0.3058 (3) | 0.24466 (7) | 0.0831 (8) | |
C1 | 0.5395 (3) | 0.8210 (3) | 0.40256 (7) | 0.0585 (7) | |
H1 | 0.4742 | 0.8076 | 0.4198 | 0.070* | |
C2 | 0.5201 (3) | 0.9159 (3) | 0.37571 (7) | 0.0618 (8) | |
H2A | 0.4433 | 0.9675 | 0.3749 | 0.074* | |
C3 | 0.6157 (3) | 0.9341 (3) | 0.34986 (7) | 0.0609 (8) | |
C4 | 0.7298 (3) | 0.8596 (3) | 0.35124 (8) | 0.0706 (9) | |
H4 | 0.7942 | 0.8722 | 0.3338 | 0.085* | |
C5 | 0.7479 (3) | 0.7654 (3) | 0.37893 (7) | 0.0603 (7) | |
H5 | 0.8255 | 0.7153 | 0.3801 | 0.072* | |
C6 | 0.6530 (3) | 0.7448 (2) | 0.40482 (6) | 0.0467 (6) | |
C7 | 0.6726 (3) | 0.6407 (3) | 0.43443 (7) | 0.0556 (7) | |
H7A | 0.7608 | 0.6037 | 0.4335 | 0.067* | |
H7B | 0.6594 | 0.6832 | 0.4579 | 0.067* | |
C8 | 0.5750 (2) | 0.4257 (2) | 0.45250 (6) | 0.0446 (6) | |
C9 | 0.6470 (3) | 0.4179 (3) | 0.48426 (6) | 0.0519 (7) | |
H9 | 0.7039 | 0.4887 | 0.4906 | 0.062* | |
C10 | 0.6332 (3) | 0.3037 (3) | 0.50629 (7) | 0.0579 (7) | |
H10 | 0.6796 | 0.2989 | 0.5279 | 0.069* | |
C11 | 0.5518 (3) | 0.1972 (3) | 0.49663 (7) | 0.0569 (7) | |
H11 | 0.5441 | 0.1204 | 0.5116 | 0.068* | |
C12 | 0.4814 (3) | 0.2042 (3) | 0.46473 (7) | 0.0516 (7) | |
H12 | 0.4269 | 0.1315 | 0.4582 | 0.062* | |
C13 | 0.4912 (2) | 0.3189 (2) | 0.44224 (6) | 0.0432 (6) | |
C14 | 0.4194 (2) | 0.3305 (2) | 0.40830 (6) | 0.0468 (6) | |
H14 | 0.4225 | 0.4135 | 0.3957 | 0.056* | |
C15 | 0.2227 (2) | 0.1701 (2) | 0.34450 (6) | 0.0433 (6) | |
C16 | 0.1668 (2) | 0.2204 (2) | 0.30967 (6) | 0.0434 (6) | |
C17 | 0.2254 (3) | 0.3183 (3) | 0.28839 (6) | 0.0577 (7) | |
H17 | 0.3042 | 0.3584 | 0.2953 | 0.069* | |
C18 | 0.1647 (4) | 0.3566 (3) | 0.25630 (8) | 0.0754 (9) | |
H18 | 0.2060 | 0.4225 | 0.2420 | 0.090* | |
C19 | −0.0018 (4) | 0.2118 (4) | 0.26539 (10) | 0.0844 (11) | |
H19 | −0.0811 | 0.1743 | 0.2578 | 0.101* | |
C20 | 0.0502 (3) | 0.1648 (3) | 0.29751 (8) | 0.0659 (8) | |
H20 | 0.0075 | 0.0969 | 0.3108 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1387 (9) | 0.0724 (5) | 0.0643 (5) | −0.0136 (5) | −0.0242 (5) | 0.0196 (4) |
O1 | 0.0687 (13) | 0.0485 (10) | 0.0579 (11) | −0.0163 (9) | −0.0226 (9) | 0.0114 (8) |
O2 | 0.0765 (14) | 0.0286 (9) | 0.0755 (12) | −0.0073 (9) | −0.0072 (10) | 0.0026 (8) |
N1 | 0.0522 (13) | 0.0353 (11) | 0.0509 (12) | 0.0007 (10) | −0.0078 (10) | 0.0052 (9) |
N2 | 0.0573 (13) | 0.0274 (10) | 0.0518 (12) | −0.0042 (10) | −0.0119 (10) | 0.0069 (9) |
N3 | 0.103 (2) | 0.083 (2) | 0.0632 (17) | 0.0170 (18) | −0.0243 (16) | −0.0127 (15) |
C1 | 0.0559 (18) | 0.0622 (17) | 0.0574 (16) | 0.0026 (15) | 0.0002 (13) | 0.0093 (14) |
C2 | 0.066 (2) | 0.0530 (17) | 0.0664 (18) | 0.0044 (15) | −0.0082 (16) | 0.0019 (14) |
C3 | 0.086 (2) | 0.0439 (15) | 0.0525 (16) | −0.0111 (15) | −0.0168 (16) | 0.0020 (12) |
C4 | 0.072 (2) | 0.080 (2) | 0.0592 (17) | −0.0106 (18) | 0.0075 (16) | 0.0095 (16) |
C5 | 0.0551 (18) | 0.0635 (17) | 0.0622 (17) | 0.0021 (14) | −0.0031 (14) | −0.0019 (14) |
C6 | 0.0481 (16) | 0.0425 (14) | 0.0496 (14) | −0.0098 (13) | −0.0082 (12) | −0.0019 (11) |
C7 | 0.0543 (17) | 0.0528 (15) | 0.0596 (16) | −0.0093 (13) | −0.0154 (13) | 0.0040 (13) |
C8 | 0.0442 (15) | 0.0435 (14) | 0.0461 (14) | 0.0038 (12) | −0.0004 (12) | 0.0035 (11) |
C9 | 0.0473 (16) | 0.0597 (16) | 0.0488 (15) | 0.0013 (13) | −0.0069 (12) | 0.0008 (12) |
C10 | 0.0550 (18) | 0.0764 (19) | 0.0423 (14) | 0.0105 (16) | −0.0043 (13) | 0.0103 (14) |
C11 | 0.0549 (17) | 0.0636 (18) | 0.0523 (16) | 0.0095 (15) | 0.0022 (14) | 0.0200 (13) |
C12 | 0.0497 (16) | 0.0503 (15) | 0.0548 (16) | 0.0026 (12) | 0.0035 (13) | 0.0109 (12) |
C13 | 0.0420 (15) | 0.0428 (13) | 0.0448 (13) | 0.0028 (12) | 0.0001 (11) | 0.0035 (11) |
C14 | 0.0520 (16) | 0.0365 (13) | 0.0519 (15) | −0.0014 (12) | −0.0089 (12) | 0.0083 (11) |
C15 | 0.0456 (15) | 0.0284 (12) | 0.0560 (14) | 0.0014 (11) | 0.0031 (12) | −0.0030 (11) |
C16 | 0.0484 (16) | 0.0334 (12) | 0.0484 (14) | 0.0067 (11) | −0.0024 (12) | −0.0092 (11) |
C17 | 0.0659 (19) | 0.0610 (17) | 0.0462 (15) | −0.0019 (15) | 0.0011 (13) | −0.0020 (13) |
C18 | 0.101 (3) | 0.076 (2) | 0.0492 (17) | 0.007 (2) | 0.0091 (18) | 0.0019 (15) |
C19 | 0.087 (3) | 0.075 (2) | 0.091 (3) | 0.001 (2) | −0.041 (2) | −0.013 (2) |
C20 | 0.066 (2) | 0.0510 (16) | 0.080 (2) | −0.0049 (15) | −0.0168 (17) | −0.0038 (15) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.736 (3) | C7—H7B | 0.9700 |
O1—C8 | 1.366 (3) | C8—C9 | 1.386 (3) |
O1—C7 | 1.421 (3) | C8—C13 | 1.396 (3) |
O2—C15 | 1.222 (3) | C9—C10 | 1.381 (3) |
N1—C14 | 1.265 (3) | C9—H9 | 0.9300 |
N1—N2 | 1.381 (3) | C10—C11 | 1.373 (4) |
N2—C15 | 1.337 (3) | C10—H10 | 0.9300 |
N2—H2 | 0.8600 | C11—C12 | 1.382 (4) |
N3—C19 | 1.313 (4) | C11—H11 | 0.9300 |
N3—C18 | 1.320 (4) | C12—C13 | 1.391 (3) |
C1—C2 | 1.367 (4) | C12—H12 | 0.9300 |
C1—C6 | 1.377 (4) | C13—C14 | 1.456 (3) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.376 (4) | C15—C16 | 1.489 (3) |
C2—H2A | 0.9300 | C16—C17 | 1.370 (3) |
C3—C4 | 1.372 (4) | C16—C20 | 1.382 (4) |
C4—C5 | 1.383 (4) | C17—C18 | 1.388 (4) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.376 (4) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.377 (4) |
C6—C7 | 1.502 (3) | C19—H19 | 0.9300 |
C7—H7A | 0.9700 | C20—H20 | 0.9300 |
| | | |
C8—O1—C7 | 119.33 (18) | C8—C9—H9 | 120.4 |
C14—N1—N2 | 113.77 (18) | C11—C10—C9 | 120.8 (2) |
C15—N2—N1 | 121.83 (18) | C11—C10—H10 | 119.6 |
C15—N2—H2 | 119.1 | C9—C10—H10 | 119.6 |
N1—N2—H2 | 119.1 | C10—C11—C12 | 120.0 (2) |
C19—N3—C18 | 115.9 (3) | C10—C11—H11 | 120.0 |
C2—C1—C6 | 121.8 (3) | C12—C11—H11 | 120.0 |
C2—C1—H1 | 119.1 | C11—C12—C13 | 120.7 (3) |
C6—C1—H1 | 119.1 | C11—C12—H12 | 119.6 |
C1—C2—C3 | 119.1 (3) | C13—C12—H12 | 119.6 |
C1—C2—H2A | 120.5 | C12—C13—C8 | 118.3 (2) |
C3—C2—H2A | 120.5 | C12—C13—C14 | 122.7 (2) |
C4—C3—C2 | 120.6 (3) | C8—C13—C14 | 119.0 (2) |
C4—C3—Cl1 | 120.0 (3) | N1—C14—C13 | 122.6 (2) |
C2—C3—Cl1 | 119.4 (3) | N1—C14—H14 | 118.7 |
C3—C4—C5 | 119.3 (3) | C13—C14—H14 | 118.7 |
C3—C4—H4 | 120.4 | O2—C15—N2 | 123.1 (2) |
C5—C4—H4 | 120.4 | O2—C15—C16 | 122.1 (2) |
C6—C5—C4 | 121.0 (3) | N2—C15—C16 | 114.81 (19) |
C6—C5—H5 | 119.5 | C17—C16—C20 | 117.4 (2) |
C4—C5—H5 | 119.5 | C17—C16—C15 | 123.7 (2) |
C5—C6—C1 | 118.2 (2) | C20—C16—C15 | 118.9 (2) |
C5—C6—C7 | 120.6 (2) | C16—C17—C18 | 118.7 (3) |
C1—C6—C7 | 121.1 (2) | C16—C17—H17 | 120.6 |
O1—C7—C6 | 107.17 (19) | C18—C17—H17 | 120.6 |
O1—C7—H7A | 110.3 | N3—C18—C17 | 124.5 (3) |
C6—C7—H7A | 110.3 | N3—C18—H18 | 117.8 |
O1—C7—H7B | 110.3 | C17—C18—H18 | 117.8 |
C6—C7—H7B | 110.3 | N3—C19—C20 | 124.7 (3) |
H7A—C7—H7B | 108.5 | N3—C19—H19 | 117.7 |
O1—C8—C9 | 124.4 (2) | C20—C19—H19 | 117.7 |
O1—C8—C13 | 114.6 (2) | C19—C20—C16 | 118.9 (3) |
C9—C8—C13 | 121.0 (2) | C19—C20—H20 | 120.6 |
C10—C9—C8 | 119.2 (2) | C16—C20—H20 | 120.6 |
C10—C9—H9 | 120.4 | | |
| | | |
C14—N1—N2—C15 | 177.3 (2) | C11—C12—C13—C14 | 179.7 (2) |
C6—C1—C2—C3 | 1.2 (4) | O1—C8—C13—C12 | 179.6 (2) |
C1—C2—C3—C4 | −0.9 (4) | C9—C8—C13—C12 | 0.1 (4) |
C1—C2—C3—Cl1 | 178.1 (2) | O1—C8—C13—C14 | 0.6 (3) |
C2—C3—C4—C5 | 0.1 (4) | C9—C8—C13—C14 | −178.9 (2) |
Cl1—C3—C4—C5 | −178.9 (2) | N2—N1—C14—C13 | −179.6 (2) |
C3—C4—C5—C6 | 0.5 (4) | C12—C13—C14—N1 | −6.8 (4) |
C4—C5—C6—C1 | −0.3 (4) | C8—C13—C14—N1 | 172.2 (2) |
C4—C5—C6—C7 | 179.0 (2) | N1—N2—C15—O2 | 1.3 (4) |
C2—C1—C6—C5 | −0.5 (4) | N1—N2—C15—C16 | −178.9 (2) |
C2—C1—C6—C7 | −179.8 (2) | O2—C15—C16—C17 | −149.1 (3) |
C8—O1—C7—C6 | −179.2 (2) | N2—C15—C16—C17 | 31.2 (3) |
C5—C6—C7—O1 | −113.4 (3) | O2—C15—C16—C20 | 30.1 (4) |
C1—C6—C7—O1 | 65.9 (3) | N2—C15—C16—C20 | −149.7 (2) |
C7—O1—C8—C9 | 6.7 (4) | C20—C16—C17—C18 | 0.4 (4) |
C7—O1—C8—C13 | −172.7 (2) | C15—C16—C17—C18 | 179.5 (2) |
O1—C8—C9—C10 | 179.3 (2) | C19—N3—C18—C17 | −0.8 (5) |
C13—C8—C9—C10 | −1.3 (4) | C16—C17—C18—N3 | 0.6 (4) |
C8—C9—C10—C11 | 1.6 (4) | C18—N3—C19—C20 | 0.0 (5) |
C9—C10—C11—C12 | −0.7 (4) | N3—C19—C20—C16 | 1.0 (5) |
C10—C11—C12—C13 | −0.5 (4) | C17—C16—C20—C19 | −1.1 (4) |
C11—C12—C13—C8 | 0.8 (4) | C15—C16—C20—C19 | 179.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.01 | 2.815 (2) | 156 |
C14—H14···O2i | 0.93 | 2.39 | 3.173 (3) | 141 |
Symmetry code: (i) −x+1/2, y+1/2, z. |