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The title compound, C
16H
14Cl
2N
2O
2, crystallizes in a centrosymmetric space group with one-half molecule in the asymmetric unit. The salicylideneimine moiety is almost planar. An intramolecular O—H
N hydrogen bond is observed [O—H
N = 2.611 (3) Å]. The packing of the molecules in the crystal structure is stabilized by π–π stacking interactions between salicylideneimine moieties.
Supporting information
CCDC reference: 248832
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.132
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: WinAFC (Rigaku/MSC, 2003); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003).
Crystal data top
C16H14Cl2N2O2 | F(000) = 348.00 |
Mr = 337.19 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.379 (2) Å | θ = 15.1–17.1° |
b = 11.655 (3) Å | µ = 0.43 mm−1 |
c = 7.322 (3) Å | T = 298 K |
β = 105.31 (3)° | Prismatic, yellow |
V = 772.0 (4) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −6→12 |
4540 measured reflections | k = 0→15 |
1776 independent reflections | l = −9→9 |
1069 reflections with F2 > 2σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.026 | intensity decay: 0.8% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[0.0031Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.132 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.33 e Å−3 |
1072 reflections | Δρmin = −0.28 e Å−3 |
107 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.84953 (8) | 0.13759 (7) | 0.4783 (1) | 0.0651 (3) | |
O1 | 0.3779 (2) | −0.1977 (2) | 0.1936 (3) | 0.0687 (7) | |
N1 | 0.2025 (2) | −0.0265 (2) | 0.0576 (3) | 0.0517 (7) | |
C1 | 0.4846 (3) | −0.1184 (2) | 0.2567 (4) | 0.0450 (7) | |
C2 | 0.6239 (3) | −0.1537 (2) | 0.3563 (4) | 0.0505 (8) | |
C3 | 0.7351 (3) | −0.0769 (2) | 0.4246 (4) | 0.0454 (7) | |
C4 | 0.7071 (3) | 0.0395 (2) | 0.3910 (4) | 0.0430 (7) | |
C5 | 0.5695 (3) | 0.0772 (2) | 0.2929 (3) | 0.0456 (7) | |
C6 | 0.4557 (3) | −0.0000 (2) | 0.2237 (3) | 0.0405 (7) | |
C7 | 0.3090 (3) | 0.0408 (3) | 0.1221 (4) | 0.0489 (7) | |
C8 | 0.0593 (3) | 0.0206 (3) | −0.0442 (4) | 0.0596 (9) | |
H1 | 0.2808 | −0.1635 | 0.1477 | 0.077* | |
H2 | 0.6428 | −0.2333 | 0.3778 | 0.059* | |
H3 | 0.8305 | −0.1017 | 0.4943 | 0.053* | |
H4 | 0.5523 | 0.1571 | 0.2724 | 0.054* | |
H5 | 0.2934 | 0.1210 | 0.1039 | 0.058* | |
H6 | 0.0635 | 0.1020 | −0.0371 | 0.068* | |
H7 | 0.0360 | −0.0025 | −0.1730 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0446 (4) | 0.0643 (5) | 0.0787 (6) | −0.0115 (3) | 0.0028 (4) | 0.0045 (4) |
O1 | 0.041 (1) | 0.052 (1) | 0.097 (2) | 0.0011 (9) | −0.009 (1) | −0.017 (1) |
N1 | 0.032 (1) | 0.070 (1) | 0.048 (1) | 0.009 (1) | 0.001 (1) | 0.003 (1) |
C1 | 0.036 (1) | 0.048 (1) | 0.048 (1) | 0.004 (1) | 0.006 (1) | −0.008 (1) |
C2 | 0.044 (2) | 0.045 (1) | 0.057 (2) | 0.011 (1) | 0.003 (1) | −0.002 (1) |
C3 | 0.031 (1) | 0.055 (2) | 0.046 (1) | 0.007 (1) | 0.002 (1) | −0.002 (1) |
C4 | 0.035 (1) | 0.053 (1) | 0.039 (1) | 0.000 (1) | 0.007 (1) | 0.000 (1) |
C5 | 0.042 (1) | 0.047 (1) | 0.047 (1) | 0.006 (1) | 0.011 (1) | 0.005 (1) |
C6 | 0.032 (1) | 0.049 (1) | 0.038 (1) | 0.008 (1) | 0.006 (1) | 0.003 (1) |
C7 | 0.035 (1) | 0.059 (2) | 0.050 (2) | 0.011 (1) | 0.007 (1) | 0.009 (1) |
C8 | 0.032 (1) | 0.080 (2) | 0.058 (2) | 0.015 (1) | −0.005 (1) | 0.007 (1) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.746 (3) | C3—H3 | 0.9505 |
O1—C1 | 1.351 (3) | C4—C5 | 1.373 (3) |
O1—H1 | 0.9693 | C5—C6 | 1.386 (3) |
N1—C7 | 1.259 (4) | C5—H4 | 0.9502 |
N1—C8 | 1.460 (3) | C6—C7 | 1.460 (3) |
C1—C2 | 1.380 (3) | C7—H5 | 0.9501 |
C1—C6 | 1.415 (4) | C8—H6 | 0.9504 |
C2—C3 | 1.365 (4) | C8—H7 | 0.9491) |
C2—H2 | 0.9498 | C8—C8i | 1.505 (4) |
C3—C4 | 1.391 (4) | | |
| | | |
C1···C4ii | 3.631 (4) | C4···C6ii | 3.574 (4) |
C1···C5ii | 3.500 (4) | C4···C7ii | 3.727 (4) |
C2···C5ii | 3.626 (4) | C5···C6ii | 3.720 (4) |
C3···C6ii | 3.615 (4) | C6···C6ii | 3.910 (3) |
C3···C7ii | 3.477 (4) | | |
| | | |
C1—O1—H1 | 112.37 | C6—C5—H4 | 119.76 |
C7—N1—C8 | 119.3 (3) | C6—C5—C4 | 120.7 (2) |
C2—C1—C6 | 119.6 (2) | H4—C5—C4 | 119.55 |
C2—C1—O1 | 119.3 (2) | C7—C6—C1 | 121.2 (2) |
C6—C1—O1 | 121.1 (2) | C7—C6—C5 | 120.4 (2) |
C3—C2—H2 | 119.25 | C1—C6—C5 | 118.4 (2) |
C3—C2—C1 | 121.5 (3) | H5—C7—N1 | 118.85 |
H2—C2—C1 | 119.21 | H5—C7—C6 | 118.78 |
C4—C3—H3 | 119.90 | N1—C7—C6 | 122.4 (3) |
C4—C3—C2 | 119.0 (2) | H6—C8—H7 | 109.44 |
H3—C3—C2 | 121.14 | H6—C8—N1 | 109.15 |
C5—C4—Cl1 | 120.3 (2) | H7—C8—N1 | 109.88 |
C5—C4—C3 | 120.8 (2) | N1—C8—C8i | 110.2 (2) |
Cl1—C4—C3 | 118.9 (2) | | |
| | | |
C8—N1—C7—C6 | −179.4 (2) | C2—C3—C4—C5 | 0.8 (4) |
O1—C1—C2—C3 | −179.4 (3) | Cl1—C4—C5—C6 | −179.8 (2) |
C6—C1—C2—C3 | 0.1 (5) | C3—C4—C5—C6 | −0.5 (4) |
O1—C1—C6—C5 | 179.7 (3) | C4—C5—C6—C1 | 0.0 (4) |
O1—C1—C6—C7 | 0.7 (4) | C4—C5—C6—C7 | 179.0 (3) |
C2—C1—C6—C5 | 0.2 (4) | C1—C6—C7—N1 | −0.7 (4) |
C2—C1—C6—C7 | −178.8 (3) | C5—C6—C7—N1 | −179.7 (3) |
C1—C2—C3—C4 | −0.6 (4) | C7—N1—C8—C8i | −125.2 (3) |
C2—C3—C4—Cl1 | −179.9 (2) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.97 | 1.80 | 2.611 (3) | 138 |
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