


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681004540X/hb5727sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053681004540X/hb5727Isup2.hkl |
CCDC reference: 803137
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.140
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 2-chloro-3-formyl-8-methylquinoline (0.2 g, 1 mM) and ethylenediamine (0.03 ml, 0.5 mM) was stirred in dichloromethane for 3 h at room temperature. The solvent from the reaction mixture was removed under reduced pressure. The resulting solid was dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and hexane. Recrystallization was by slow evaporation of a dichloromethane solution which yielded yellow prisms of (I). Yield: 65%. M.pt. 475–477 K.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C).
Interest in the title compound arises as a result of the recent report of the photophysical properties of Schiff base complexes derivativatized with quinoline residues (Liu et al., 2010). The title molecule, Fig. 1, is disposed about a centre of inversion so that the pendent quinoline groups are co-planar. Owing to the twist in the central ethylene bridge, there is a kink in the molecule as manifested in the value of the C2—N1—C1—C1i torsion angle of -147.0 (3) °; i: 1 - x, 1 - y, 1 - z. There is a smaller twist between the imine [N1═C2 = 1.267 (3) Å] and quinoline residues as seen in the N1—C2—C3—C5 torsion angle of -12.4 (4) °.
The crystal packing is dominated by weak π–π and C—H···N contacts that lead to the formation of a supramolecular chain along the b axis, Fig. 2. The π–π contacts occur between translationally related quinoline rings [ring centroid(N2,C3–C6,C11)···ring centroid(C6–C11)ii = 3.5670 (14) Å with an angle of inclination = 0.41 (11) ° for ii: x, -1 + y, z] and the C—H···N contacts occur between the methylene-H and imine-N1 atoms, Table 1. Chains pack as shown in Fig. 3.
For background to the photophysical properties of Schiff base complexes derivativatized with quinoline residues, see: Liu et al. (2010).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
C24H20Cl2N4 | F(000) = 452 |
Mr = 435.34 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1737 reflections |
a = 18.363 (2) Å | θ = 2.9–28.1° |
b = 3.9494 (5) Å | µ = 0.34 mm−1 |
c = 14.1726 (19) Å | T = 100 K |
β = 99.056 (2)° | Prism, yellow |
V = 1015.0 (2) Å3 | 0.30 × 0.15 × 0.05 mm |
Z = 2 |
Bruker SMART APEX diffractometer | 2324 independent reflections |
Radiation source: fine-focus sealed tube | 1863 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→21 |
Tmin = 0.756, Tmax = 0.862 | k = −5→5 |
8859 measured reflections | l = −18→18 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.073P)2 + 0.7018P] where P = (Fo2 + 2Fc2)/3 |
2324 reflections | (Δ/σ)max = 0.001 |
137 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C24H20Cl2N4 | V = 1015.0 (2) Å3 |
Mr = 435.34 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.363 (2) Å | µ = 0.34 mm−1 |
b = 3.9494 (5) Å | T = 100 K |
c = 14.1726 (19) Å | 0.30 × 0.15 × 0.05 mm |
β = 99.056 (2)° |
Bruker SMART APEX diffractometer | 2324 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1863 reflections with I > 2σ(I) |
Tmin = 0.756, Tmax = 0.862 | Rint = 0.055 |
8859 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.72 e Å−3 |
2324 reflections | Δρmin = −0.46 e Å−3 |
137 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.66489 (3) | 0.91685 (16) | 0.86511 (4) | 0.0207 (2) | |
N1 | 0.57606 (11) | 0.7565 (5) | 0.56683 (14) | 0.0198 (4) | |
N2 | 0.77325 (10) | 1.1953 (5) | 0.79768 (12) | 0.0146 (4) | |
C1 | 0.50497 (13) | 0.5852 (7) | 0.54853 (16) | 0.0193 (5) | |
H1A | 0.4649 | 0.7516 | 0.5505 | 0.023* | |
H1B | 0.5022 | 0.4137 | 0.5988 | 0.023* | |
C2 | 0.60887 (13) | 0.7696 (6) | 0.65240 (16) | 0.0182 (5) | |
H2 | 0.5878 | 0.6618 | 0.7016 | 0.022* | |
C3 | 0.67969 (12) | 0.9510 (6) | 0.67619 (16) | 0.0163 (5) | |
C4 | 0.71175 (12) | 1.0337 (6) | 0.77157 (15) | 0.0156 (5) | |
C5 | 0.71871 (12) | 1.0545 (6) | 0.60569 (15) | 0.0159 (5) | |
H5 | 0.6999 | 1.0076 | 0.5407 | 0.019* | |
C6 | 0.78589 (12) | 1.2285 (6) | 0.62878 (14) | 0.0144 (5) | |
C7 | 0.82776 (13) | 1.3369 (6) | 0.55873 (15) | 0.0161 (5) | |
H7 | 0.8108 | 1.2934 | 0.4930 | 0.019* | |
C8 | 0.89247 (13) | 1.5042 (6) | 0.58613 (15) | 0.0176 (5) | |
H8 | 0.9209 | 1.5741 | 0.5391 | 0.021* | |
C9 | 0.91795 (12) | 1.5753 (6) | 0.68373 (15) | 0.0163 (5) | |
H9 | 0.9630 | 1.6950 | 0.7008 | 0.020* | |
C10 | 0.87912 (12) | 1.4754 (6) | 0.75412 (15) | 0.0142 (5) | |
C11 | 0.81194 (12) | 1.2958 (6) | 0.72724 (15) | 0.0141 (5) | |
C12 | 0.90516 (13) | 1.5567 (6) | 0.85775 (15) | 0.0181 (5) | |
H12A | 0.9508 | 1.6891 | 0.8637 | 0.027* | |
H12B | 0.9144 | 1.3457 | 0.8941 | 0.027* | |
H12C | 0.8672 | 1.6880 | 0.8829 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0217 (3) | 0.0290 (4) | 0.0120 (3) | −0.0042 (2) | 0.0040 (2) | 0.0005 (2) |
N1 | 0.0181 (10) | 0.0211 (11) | 0.0184 (10) | −0.0028 (8) | −0.0021 (7) | 0.0020 (8) |
N2 | 0.0164 (10) | 0.0186 (10) | 0.0089 (8) | 0.0010 (8) | 0.0022 (7) | 0.0005 (7) |
C1 | 0.0185 (12) | 0.0208 (12) | 0.0176 (12) | −0.0030 (10) | −0.0003 (9) | −0.0001 (9) |
C2 | 0.0184 (11) | 0.0191 (12) | 0.0168 (11) | −0.0001 (9) | 0.0019 (8) | −0.0006 (9) |
C3 | 0.0178 (11) | 0.0160 (12) | 0.0144 (10) | 0.0022 (9) | −0.0001 (8) | −0.0012 (9) |
C4 | 0.0187 (12) | 0.0171 (12) | 0.0114 (10) | 0.0016 (9) | 0.0031 (8) | 0.0019 (8) |
C5 | 0.0201 (12) | 0.0172 (11) | 0.0095 (9) | 0.0020 (9) | −0.0009 (8) | −0.0008 (8) |
C6 | 0.0182 (11) | 0.0150 (11) | 0.0093 (10) | 0.0039 (9) | 0.0005 (8) | −0.0002 (8) |
C7 | 0.0200 (12) | 0.0209 (12) | 0.0071 (9) | 0.0046 (9) | 0.0009 (8) | 0.0011 (8) |
C8 | 0.0203 (12) | 0.0221 (12) | 0.0109 (10) | 0.0038 (9) | 0.0041 (8) | 0.0018 (8) |
C9 | 0.0172 (11) | 0.0171 (12) | 0.0141 (10) | 0.0004 (9) | 0.0006 (8) | 0.0000 (9) |
C10 | 0.0190 (11) | 0.0145 (11) | 0.0086 (9) | 0.0031 (9) | 0.0009 (8) | −0.0006 (8) |
C11 | 0.0159 (11) | 0.0163 (11) | 0.0097 (10) | 0.0029 (9) | 0.0012 (8) | 0.0007 (8) |
C12 | 0.0194 (11) | 0.0252 (13) | 0.0088 (10) | −0.0030 (10) | −0.0005 (8) | −0.0018 (9) |
Cl1—C4 | 1.752 (2) | C6—C7 | 1.414 (3) |
N1—C2 | 1.267 (3) | C6—C11 | 1.427 (3) |
N1—C1 | 1.457 (3) | C7—C8 | 1.362 (3) |
N2—C4 | 1.299 (3) | C7—H7 | 0.9500 |
N2—C11 | 1.372 (3) | C8—C9 | 1.417 (3) |
C1—C1i | 1.517 (4) | C8—H8 | 0.9500 |
C1—H1A | 0.9900 | C9—C10 | 1.372 (3) |
C1—H1B | 0.9900 | C9—H9 | 0.9500 |
C2—C3 | 1.477 (3) | C10—C11 | 1.422 (3) |
C2—H2 | 0.9500 | C10—C12 | 1.506 (3) |
C3—C5 | 1.380 (3) | C12—H12A | 0.9800 |
C3—C4 | 1.425 (3) | C12—H12B | 0.9800 |
C5—C6 | 1.405 (3) | C12—H12C | 0.9800 |
C5—H5 | 0.9500 | ||
C2—N1—C1 | 117.8 (2) | C7—C6—C11 | 119.6 (2) |
C4—N2—C11 | 117.47 (18) | C8—C7—C6 | 119.5 (2) |
N1—C1—C1i | 110.1 (2) | C8—C7—H7 | 120.2 |
N1—C1—H1A | 109.6 | C6—C7—H7 | 120.2 |
C1i—C1—H1A | 109.6 | C7—C8—C9 | 120.9 (2) |
N1—C1—H1B | 109.6 | C7—C8—H8 | 119.5 |
C1i—C1—H1B | 109.6 | C9—C8—H8 | 119.5 |
H1A—C1—H1B | 108.1 | C10—C9—C8 | 121.6 (2) |
N1—C2—C3 | 120.5 (2) | C10—C9—H9 | 119.2 |
N1—C2—H2 | 119.8 | C8—C9—H9 | 119.2 |
C3—C2—H2 | 119.8 | C9—C10—C11 | 118.47 (19) |
C5—C3—C4 | 115.8 (2) | C9—C10—C12 | 121.8 (2) |
C5—C3—C2 | 121.2 (2) | C11—C10—C12 | 119.77 (19) |
C4—C3—C2 | 123.1 (2) | N2—C11—C10 | 118.43 (19) |
N2—C4—C3 | 126.4 (2) | N2—C11—C6 | 121.7 (2) |
N2—C4—Cl1 | 114.97 (16) | C10—C11—C6 | 119.9 (2) |
C3—C4—Cl1 | 118.60 (18) | C10—C12—H12A | 109.5 |
C3—C5—C6 | 120.9 (2) | C10—C12—H12B | 109.5 |
C3—C5—H5 | 119.6 | H12A—C12—H12B | 109.5 |
C6—C5—H5 | 119.6 | C10—C12—H12C | 109.5 |
C5—C6—C7 | 122.61 (19) | H12A—C12—H12C | 109.5 |
C5—C6—C11 | 117.8 (2) | H12B—C12—H12C | 109.5 |
C2—N1—C1—C1i | −147.0 (3) | C11—C6—C7—C8 | 0.1 (3) |
C1—N1—C2—C3 | −177.6 (2) | C6—C7—C8—C9 | −0.9 (3) |
N1—C2—C3—C5 | −12.4 (4) | C7—C8—C9—C10 | 0.8 (4) |
N1—C2—C3—C4 | 167.0 (2) | C8—C9—C10—C11 | 0.1 (3) |
C11—N2—C4—C3 | −0.4 (4) | C8—C9—C10—C12 | −178.7 (2) |
C11—N2—C4—Cl1 | −179.41 (16) | C4—N2—C11—C10 | 179.5 (2) |
C5—C3—C4—N2 | 0.1 (4) | C4—N2—C11—C6 | 0.4 (3) |
C2—C3—C4—N2 | −179.3 (2) | C9—C10—C11—N2 | 179.8 (2) |
C5—C3—C4—Cl1 | 179.03 (17) | C12—C10—C11—N2 | −1.3 (3) |
C2—C3—C4—Cl1 | −0.3 (3) | C9—C10—C11—C6 | −1.0 (3) |
C4—C3—C5—C6 | 0.3 (3) | C12—C10—C11—C6 | 177.9 (2) |
C2—C3—C5—C6 | 179.7 (2) | C5—C6—C11—N2 | 0.1 (3) |
C3—C5—C6—C7 | 179.6 (2) | C7—C6—C11—N2 | −180.0 (2) |
C3—C5—C6—C11 | −0.4 (3) | C5—C6—C11—C10 | −179.1 (2) |
C5—C6—C7—C8 | −180.0 (2) | C7—C6—C11—C10 | 0.9 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1a···N1ii | 0.99 | 2.59 | 3.299 (3) | 128 |
Symmetry code: (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C24H20Cl2N4 |
Mr | 435.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 18.363 (2), 3.9494 (5), 14.1726 (19) |
β (°) | 99.056 (2) |
V (Å3) | 1015.0 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.30 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART APEX |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.756, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8859, 2324, 1863 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.140, 1.05 |
No. of reflections | 2324 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.46 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1a···N1i | 0.99 | 2.59 | 3.299 (3) | 128 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Interest in the title compound arises as a result of the recent report of the photophysical properties of Schiff base complexes derivativatized with quinoline residues (Liu et al., 2010). The title molecule, Fig. 1, is disposed about a centre of inversion so that the pendent quinoline groups are co-planar. Owing to the twist in the central ethylene bridge, there is a kink in the molecule as manifested in the value of the C2—N1—C1—C1i torsion angle of -147.0 (3) °; i: 1 - x, 1 - y, 1 - z. There is a smaller twist between the imine [N1═C2 = 1.267 (3) Å] and quinoline residues as seen in the N1—C2—C3—C5 torsion angle of -12.4 (4) °.
The crystal packing is dominated by weak π–π and C—H···N contacts that lead to the formation of a supramolecular chain along the b axis, Fig. 2. The π–π contacts occur between translationally related quinoline rings [ring centroid(N2,C3–C6,C11)···ring centroid(C6–C11)ii = 3.5670 (14) Å with an angle of inclination = 0.41 (11) ° for ii: x, -1 + y, z] and the C—H···N contacts occur between the methylene-H and imine-N1 atoms, Table 1. Chains pack as shown in Fig. 3.