Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050532/bt2540sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050532/bt2540Isup2.hkl |
CCDC reference: 667410
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.121
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C22 H28 N2 O6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see Khalaji et al. (2006, 2007). For related structures, see Li et al.(2006), Yang et al. (2007), Bomfim et al. (2005), Glidewell et al. (2006), Sun et al. (2004), Xiao et al. (2006) and Bahron et al. (2007).
Ethylenediamine (1 mmol, 60 mg) and 3,4,5-trimethoxybenzaldehyde (2 mmol, 392 mg) were dissolved in methanol (15 ml) at 328 K. The mixture was stirred for 15 min to give a clear and colorless solution. After the solution had been allowed to stand in air for 1 d, colorless crystals formed, in about 91% yield, on slow evaporation of the solvent.
All H atoms were positioned geometrically (C—H=0.93–0.97 Å), and refined as riding with Uiso(H)=1.2Ueq(carrier) or 1.5eq(methyl groups). The methyl groups were allowed to rotate but not to tip.
Schiff bases are used extensively as ligands in the field of coordination chemistry, because they are potentially capable of forming stable complexes with metal ions, such as Ag(I) and Cu(I) (Khalaji et al., 2006, and 2007). The crystal structures of some diamine Schiff bases have been reported (Li et al., 2006.; Yang et al., 2007.; Bomfim et al., 2005.; Glidewell et al., 2006.; Sun et al., 2004.; Xiao et al., 2006.; Bahron et al., 2007). Here we report the crystal structure of the diamine Schiff base, N,N'-Bis(3,4,5-trimethoxybenzylidene) ethylenediamine.
In N,N'-Bis(3,4,5-trimethoxybenzylidene)ethylenediamine (Fig. 1), two 3,4,5-trimethoxybenzylidene groups are bridged by the ethylenediamine fragment via two C=N double bonds. All the bond lengths and angles are within normal ranges. The N(1)=C(2) bond length of 1.257 (3) Å conforms to the value for a double bond, while the C(1)—N(1) bond length of 1.463 (2) Å conforms to the value for a single bond and are comparable to the corresponding values observed in N,N'-bis(3,4-dimethoxybenzylidene) ethylenediamine (Li et al., 2006) and N,N'-Bis(4-nitrobenzylidene) ethane-1,2-diamine (Sun et al., 2004).
For general background, see Khalaji et al. (2006, 2007). For related structures, see Li et al.(2006), Yang et al. (2007), Bomfim et al. (2005), Glidewell et al. (2006), Sun et al. (2004), Xiao et al. (2006) and Bahron et al. (2007).
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. A view of the molecular of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
C22H28N2O6 | F(000) = 888 |
Mr = 416.46 | Dx = 1.266 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 32.008 (8) Å | Cell parameters from 1598 reflections |
b = 4.9175 (12) Å | θ = 2.9–23.8° |
c = 13.945 (4) Å | µ = 0.09 mm−1 |
β = 95.326 (4)° | T = 294 K |
V = 2185.4 (9) Å3 | Block, colorless |
Z = 4 | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 1933 independent reflections |
Radiation source: fine-focus sealed tube | 1321 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −38→37 |
Tmin = 0.978, Tmax = 0.984 | k = −5→3 |
5347 measured reflections | l = −15→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.163P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1933 reflections | Δρmax = 0.18 e Å−3 |
140 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0070 (10) |
C22H28N2O6 | V = 2185.4 (9) Å3 |
Mr = 416.46 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.008 (8) Å | µ = 0.09 mm−1 |
b = 4.9175 (12) Å | T = 294 K |
c = 13.945 (4) Å | 0.24 × 0.22 × 0.18 mm |
β = 95.326 (4)° |
Bruker SMART CCD area-detector diffractometer | 1933 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1321 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.984 | Rint = 0.030 |
5347 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
1933 reflections | Δρmin = −0.14 e Å−3 |
140 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 | ||
O1 | 0.13907 (4) | 0.4533 (3) | 0.20272 (9) | 0.0587 (4) | |
O2 | 0.20178 (3) | 0.1274 (2) | 0.15836 (8) | 0.0436 (4) | |
O3 | 0.19633 (3) | −0.1625 (3) | −0.00262 (8) | 0.0464 (4) | |
N1 | 0.04056 (5) | −0.0432 (4) | −0.14559 (12) | 0.0584 (5) | |
C1 | −0.00111 (6) | −0.0261 (6) | −0.19801 (15) | 0.0719 (7) | |
H1A | −0.0179 | −0.1793 | −0.1805 | 0.086* | |
H1B | −0.0148 | 0.1391 | −0.1795 | 0.086* | |
C2 | 0.04917 (5) | 0.1186 (5) | −0.07681 (14) | 0.0535 (6) | |
H2 | 0.0286 | 0.2422 | −0.0625 | 0.064* | |
C3 | 0.08967 (5) | 0.1253 (4) | −0.01738 (12) | 0.0418 (5) | |
C4 | 0.09424 (5) | 0.2955 (4) | 0.06202 (12) | 0.0447 (5) | |
H4 | 0.0722 | 0.4075 | 0.0758 | 0.054* | |
C5 | 0.13159 (5) | 0.2998 (4) | 0.12105 (12) | 0.0415 (5) | |
C6 | 0.16516 (5) | 0.1380 (4) | 0.09854 (11) | 0.0368 (4) | |
C7 | 0.16099 (5) | −0.0248 (3) | 0.01564 (12) | 0.0362 (4) | |
C8 | 0.12310 (5) | −0.0372 (4) | −0.04093 (12) | 0.0396 (5) | |
H8 | 0.1199 | −0.1524 | −0.0940 | 0.047* | |
C9 | 0.10634 (6) | 0.6251 (5) | 0.22895 (15) | 0.0632 (6) | |
H9A | 0.0980 | 0.7463 | 0.1767 | 0.095* | |
H9B | 0.1161 | 0.7290 | 0.2849 | 0.095* | |
H9C | 0.0828 | 0.5163 | 0.2430 | 0.095* | |
C10 | 0.22852 (6) | 0.3588 (4) | 0.15304 (15) | 0.0549 (6) | |
H10A | 0.2379 | 0.3699 | 0.0898 | 0.082* | |
H10B | 0.2523 | 0.3411 | 0.1999 | 0.082* | |
H10C | 0.2133 | 0.5208 | 0.1659 | 0.082* | |
C11 | 0.19456 (6) | −0.3240 (4) | −0.08760 (14) | 0.0551 (6) | |
H11A | 0.1744 | −0.4673 | −0.0834 | 0.083* | |
H11B | 0.2217 | −0.4013 | −0.0941 | 0.083* | |
H11C | 0.1863 | −0.2124 | −0.1426 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0538 (8) | 0.0740 (10) | 0.0457 (8) | 0.0172 (7) | −0.0087 (6) | −0.0196 (7) |
O2 | 0.0399 (7) | 0.0451 (8) | 0.0420 (7) | −0.0001 (6) | −0.0160 (5) | 0.0015 (6) |
O3 | 0.0390 (7) | 0.0554 (8) | 0.0426 (7) | 0.0107 (6) | −0.0082 (5) | −0.0079 (6) |
N1 | 0.0357 (9) | 0.0874 (13) | 0.0490 (10) | −0.0026 (9) | −0.0134 (8) | 0.0026 (10) |
C1 | 0.0338 (11) | 0.124 (2) | 0.0542 (12) | −0.0077 (12) | −0.0137 (10) | −0.0004 (13) |
C2 | 0.0343 (10) | 0.0823 (16) | 0.0427 (11) | 0.0048 (10) | −0.0022 (8) | 0.0055 (11) |
C3 | 0.0334 (9) | 0.0557 (12) | 0.0351 (10) | −0.0013 (9) | −0.0037 (7) | 0.0078 (9) |
C4 | 0.0353 (9) | 0.0568 (13) | 0.0415 (10) | 0.0082 (9) | 0.0000 (8) | 0.0047 (9) |
C5 | 0.0425 (10) | 0.0476 (11) | 0.0334 (9) | 0.0024 (9) | −0.0015 (7) | 0.0006 (8) |
C6 | 0.0347 (9) | 0.0413 (10) | 0.0323 (9) | 0.0009 (8) | −0.0072 (7) | 0.0060 (8) |
C7 | 0.0336 (9) | 0.0382 (10) | 0.0354 (9) | 0.0004 (8) | −0.0038 (7) | 0.0057 (8) |
C8 | 0.0385 (10) | 0.0451 (11) | 0.0335 (9) | −0.0031 (8) | −0.0051 (8) | 0.0016 (8) |
C9 | 0.0611 (13) | 0.0706 (15) | 0.0577 (13) | 0.0142 (11) | 0.0050 (10) | −0.0170 (11) |
C10 | 0.0449 (11) | 0.0576 (13) | 0.0585 (13) | −0.0039 (10) | −0.0143 (9) | −0.0004 (10) |
C11 | 0.0537 (12) | 0.0619 (14) | 0.0489 (12) | 0.0092 (11) | −0.0003 (9) | −0.0131 (10) |
O1—C5 | 1.369 (2) | C4—C5 | 1.387 (2) |
O1—C9 | 1.420 (2) | C4—H4 | 0.9300 |
O2—C6 | 1.3751 (18) | C5—C6 | 1.396 (2) |
O2—C10 | 1.430 (2) | C6—C7 | 1.402 (2) |
O3—C7 | 1.363 (2) | C7—C8 | 1.385 (2) |
O3—C11 | 1.423 (2) | C8—H8 | 0.9300 |
N1—C2 | 1.257 (3) | C9—H9A | 0.9600 |
N1—C1 | 1.463 (2) | C9—H9B | 0.9600 |
C1—C1i | 1.458 (4) | C9—H9C | 0.9600 |
C1—H1A | 0.9700 | C10—H10A | 0.9600 |
C1—H1B | 0.9700 | C10—H10B | 0.9600 |
C2—C3 | 1.473 (2) | C10—H10C | 0.9600 |
C2—H2 | 0.9300 | C11—H11A | 0.9600 |
C3—C4 | 1.385 (3) | C11—H11B | 0.9600 |
C3—C8 | 1.399 (2) | C11—H11C | 0.9600 |
C5—O1—C9 | 117.79 (14) | O3—C7—C8 | 124.73 (16) |
C6—O2—C10 | 114.78 (13) | O3—C7—C6 | 114.87 (13) |
C7—O3—C11 | 117.60 (12) | C8—C7—C6 | 120.40 (16) |
C2—N1—C1 | 118.03 (19) | C7—C8—C3 | 119.30 (17) |
C1i—C1—N1 | 111.8 (2) | C7—C8—H8 | 120.3 |
C1i—C1—H1A | 109.3 | C3—C8—H8 | 120.3 |
N1—C1—H1A | 109.3 | O1—C9—H9A | 109.5 |
C1i—C1—H1B | 109.3 | O1—C9—H9B | 109.5 |
N1—C1—H1B | 109.3 | H9A—C9—H9B | 109.5 |
H1A—C1—H1B | 107.9 | O1—C9—H9C | 109.5 |
N1—C2—C3 | 124.22 (19) | H9A—C9—H9C | 109.5 |
N1—C2—H2 | 117.9 | H9B—C9—H9C | 109.5 |
C3—C2—H2 | 117.9 | O2—C10—H10A | 109.5 |
C4—C3—C8 | 120.44 (15) | O2—C10—H10B | 109.5 |
C4—C3—C2 | 119.04 (17) | H10A—C10—H10B | 109.5 |
C8—C3—C2 | 120.52 (17) | O2—C10—H10C | 109.5 |
C3—C4—C5 | 120.33 (17) | H10A—C10—H10C | 109.5 |
C3—C4—H4 | 119.8 | H10B—C10—H10C | 109.5 |
C5—C4—H4 | 119.8 | O3—C11—H11A | 109.5 |
O1—C5—C4 | 125.23 (16) | O3—C11—H11B | 109.5 |
O1—C5—C6 | 114.99 (15) | H11A—C11—H11B | 109.5 |
C4—C5—C6 | 119.78 (16) | O3—C11—H11C | 109.5 |
O2—C6—C5 | 121.03 (15) | H11A—C11—H11C | 109.5 |
O2—C6—C7 | 119.30 (14) | H11B—C11—H11C | 109.5 |
C5—C6—C7 | 119.62 (15) | ||
C2—N1—C1—C1i | 132.79 (15) | C4—C5—C6—O2 | −176.60 (16) |
C1—N1—C2—C3 | 179.87 (18) | O1—C5—C6—C7 | −179.22 (15) |
N1—C2—C3—C4 | −174.11 (19) | C4—C5—C6—C7 | 0.9 (3) |
N1—C2—C3—C8 | 6.1 (3) | C11—O3—C7—C8 | 2.1 (2) |
C8—C3—C4—C5 | −2.2 (3) | C11—O3—C7—C6 | −177.88 (15) |
C2—C3—C4—C5 | 177.99 (17) | O2—C6—C7—O3 | −6.1 (2) |
C9—O1—C5—C4 | −0.9 (3) | C5—C6—C7—O3 | 176.40 (15) |
C9—O1—C5—C6 | 179.21 (16) | O2—C6—C7—C8 | 173.94 (15) |
C3—C4—C5—O1 | −177.88 (16) | C5—C6—C7—C8 | −3.6 (2) |
C3—C4—C5—C6 | 2.0 (3) | O3—C7—C8—C3 | −176.62 (15) |
C10—O2—C6—C5 | −76.5 (2) | C6—C7—C8—C3 | 3.4 (2) |
C10—O2—C6—C7 | 105.98 (18) | C4—C3—C8—C7 | −0.5 (3) |
O1—C5—C6—O2 | 3.3 (2) | C2—C3—C8—C7 | 179.31 (17) |
Symmetry code: (i) −x, y, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H28N2O6 |
Mr | 416.46 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 32.008 (8), 4.9175 (12), 13.945 (4) |
β (°) | 95.326 (4) |
V (Å3) | 2185.4 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.978, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5347, 1933, 1321 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.121, 1.03 |
No. of reflections | 1933 |
No. of parameters | 140 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.14 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
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Schiff bases are used extensively as ligands in the field of coordination chemistry, because they are potentially capable of forming stable complexes with metal ions, such as Ag(I) and Cu(I) (Khalaji et al., 2006, and 2007). The crystal structures of some diamine Schiff bases have been reported (Li et al., 2006.; Yang et al., 2007.; Bomfim et al., 2005.; Glidewell et al., 2006.; Sun et al., 2004.; Xiao et al., 2006.; Bahron et al., 2007). Here we report the crystal structure of the diamine Schiff base, N,N'-Bis(3,4,5-trimethoxybenzylidene) ethylenediamine.
In N,N'-Bis(3,4,5-trimethoxybenzylidene)ethylenediamine (Fig. 1), two 3,4,5-trimethoxybenzylidene groups are bridged by the ethylenediamine fragment via two C=N double bonds. All the bond lengths and angles are within normal ranges. The N(1)=C(2) bond length of 1.257 (3) Å conforms to the value for a double bond, while the C(1)—N(1) bond length of 1.463 (2) Å conforms to the value for a single bond and are comparable to the corresponding values observed in N,N'-bis(3,4-dimethoxybenzylidene) ethylenediamine (Li et al., 2006) and N,N'-Bis(4-nitrobenzylidene) ethane-1,2-diamine (Sun et al., 2004).