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The mol­ecule of the title compound, C22H30N4, lies across a crystallographic inversion centre and adopts an E configuration with respect to the azomethine C=N bond. The mol­ecular structure has a staggered conformation, with the two benzene rings parallel to each other. The dihedral angle between the benzyl­idene and butane groups is 77.77 (7)°. In the crystal structure, mol­ecules are arranged into columns along the a axis by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049914/sj2369sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049914/sj2369Isup2.hkl
Contains datablock I

CCDC reference: 667365

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.050
  • wR factor = 0.148
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.757 Test value = 0.700 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.76 e/A   
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 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 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff bases readily form stable complexes with most transition metal ions (Amirnasr et al., 2002; Habibi et al., 2007; Pal et al., 2005) and show biological activity (Adsule et al., 2006; Hou et al., 2001; Ren et al., 2002). In this paper, we report the crystal structure of the title Schiff base compound.

The molecule of the title compound lies across an crystallographic inversion centre and the asymmetric unit therefore contains one-half of the molecule (Fig. 1). The molecular structure of the title compound is non-planar but is in a staggered conformation about the C1–C1A bond [symmetry code (A): 1 - x, 1 - y, -z]. The two benzene rings are parallel to each other, the dihedral angle between the planar benzylidene (C4–C9/C3/N1) and the planar bridging butane (C1/C2/C1A/C2A) [symmetry code (A): 1 - x, 1 - y, -z] groups is 77.77 (7) °. The dimethylamino group is slightly twisted respect to the attached benzene ring as indicated by torsion angles of C10/N2/C7/C6 = -5.55 (11) ° and C11/N2/C7/C8 = 16.80 (11)°. Bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to closely related structures (Bahron et al., 2007; Kassim et al., 2006).

In the crystal structure, Fig. 2, molecules are arranged into columns along the a axis by C—H ···π interactions (Table 1); Cg1 is the centroid of C4–C9 benzene ring.

Related literature top

For the values of bond lengths and angles, see Allen et al. (1987). For related structures, see, for example, Bahron et al. (2007); Kassim et al. (2006). For information on Schiff base complexes and their pharmacological activities, see, for example, Adsule et al. (2006); Amirnasr et al. (2002); Habibi et al. (2007); Hou et al. (2001); Pal et al. (2005); Ren et al. (2002).

Experimental top

The title compound was prepared by mixing a solution of butane-1,4-diamine (1 mmol) dissolved in chloroform (3 ml) and 4-dimethylamino benzaldehyde (2 mmol) dissolved in chloroform (3 ml) and stirring the mixture under reflux for 8 h. Colorless single crystals suitable for x-ray structure determination were obtained after recrystallization by slow evaporation from an ethanol solution at room temperature after several days.

Refinement top

All H atoms were located in a difference map and isotropically refined. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The final difference Fourier map showed a high peak 0.97 Å from C1.

Structure description top

Schiff bases readily form stable complexes with most transition metal ions (Amirnasr et al., 2002; Habibi et al., 2007; Pal et al., 2005) and show biological activity (Adsule et al., 2006; Hou et al., 2001; Ren et al., 2002). In this paper, we report the crystal structure of the title Schiff base compound.

The molecule of the title compound lies across an crystallographic inversion centre and the asymmetric unit therefore contains one-half of the molecule (Fig. 1). The molecular structure of the title compound is non-planar but is in a staggered conformation about the C1–C1A bond [symmetry code (A): 1 - x, 1 - y, -z]. The two benzene rings are parallel to each other, the dihedral angle between the planar benzylidene (C4–C9/C3/N1) and the planar bridging butane (C1/C2/C1A/C2A) [symmetry code (A): 1 - x, 1 - y, -z] groups is 77.77 (7) °. The dimethylamino group is slightly twisted respect to the attached benzene ring as indicated by torsion angles of C10/N2/C7/C6 = -5.55 (11) ° and C11/N2/C7/C8 = 16.80 (11)°. Bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to closely related structures (Bahron et al., 2007; Kassim et al., 2006).

In the crystal structure, Fig. 2, molecules are arranged into columns along the a axis by C—H ···π interactions (Table 1); Cg1 is the centroid of C4–C9 benzene ring.

For the values of bond lengths and angles, see Allen et al. (1987). For related structures, see, for example, Bahron et al. (2007); Kassim et al. (2006). For information on Schiff base complexes and their pharmacological activities, see, for example, Adsule et al. (2006); Amirnasr et al. (2002); Habibi et al. (2007); Hou et al. (2001); Pal et al. (2005); Ren et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. [Symmetry code: (A) 1 - x, 1 - y, -z].
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis. C—H···π interactions are drawn as dashed lines.
N,N'-Bis[4-(dimethylamino)benzylidene]butane-1,4-diamine top
Crystal data top
C22H30N4F(000) = 380
Mr = 350.50Dx = 1.199 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4266 reflections
a = 5.2254 (1) Åθ = 2.1–35.0°
b = 9.5742 (3) ŵ = 0.07 mm1
c = 19.4882 (5) ÅT = 100 K
β = 95.512 (1)°Block, colorless
V = 970.47 (4) Å30.57 × 0.31 × 0.19 mm
Z = 2
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4266 independent reflections
Radiation source: fine-focus sealed tube3555 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 2.1°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1514
Tmin = 0.960, Tmax = 0.987l = 3129
34188 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0875P)2 + 0.1308P]
where P = (Fo2 + 2Fc2)/3
4266 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C22H30N4V = 970.47 (4) Å3
Mr = 350.50Z = 2
Monoclinic, P21/cMo Kα radiation
a = 5.2254 (1) ŵ = 0.07 mm1
b = 9.5742 (3) ÅT = 100 K
c = 19.4882 (5) Å0.57 × 0.31 × 0.19 mm
β = 95.512 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4266 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3555 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.987Rint = 0.038
34188 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.148All H-atom parameters refined
S = 1.06Δρmax = 0.76 e Å3
4266 reflectionsΔρmin = 0.32 e Å3
178 parameters
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
N10.53637 (13)0.48735 (7)0.13556 (3)0.02030 (14)
N20.12267 (14)0.52022 (8)0.40171 (4)0.02448 (15)
C10.62461 (15)0.46510 (9)0.01434 (4)0.02237 (16)
C20.72103 (15)0.51889 (9)0.08599 (4)0.02252 (16)
C30.51689 (14)0.57613 (8)0.18350 (4)0.01926 (14)
C40.34554 (14)0.56002 (7)0.23809 (4)0.01734 (13)
C50.17727 (13)0.44685 (7)0.24139 (4)0.01744 (14)
C60.02178 (14)0.43354 (8)0.29458 (4)0.01834 (14)
C70.02565 (14)0.53483 (8)0.34753 (4)0.01792 (14)
C80.19010 (14)0.65045 (8)0.34311 (4)0.01959 (14)
C90.34678 (14)0.66113 (8)0.28991 (4)0.01941 (14)
C100.30355 (16)0.40527 (10)0.40148 (5)0.02695 (17)
C110.16521 (18)0.64055 (11)0.44456 (5)0.02906 (18)
H1A0.760 (2)0.4843 (13)0.0193 (7)0.027 (3)*
H1B0.589 (2)0.3590 (15)0.0147 (7)0.036 (3)*
H2A0.887 (2)0.4716 (13)0.1001 (7)0.029 (3)*
H2B0.758 (2)0.6201 (14)0.0852 (7)0.031 (3)*
H30.620 (3)0.6594 (15)0.1863 (7)0.038 (3)*
H50.159 (2)0.3760 (15)0.2047 (7)0.035 (3)*
H60.095 (2)0.3549 (14)0.2944 (7)0.032 (3)*
H80.204 (2)0.7260 (14)0.3775 (7)0.034 (3)*
H90.455 (2)0.7385 (14)0.2887 (7)0.030 (3)*
H10A0.214 (2)0.3155 (15)0.3995 (6)0.034 (3)*
H10B0.440 (3)0.4081 (15)0.3634 (7)0.038 (3)*
H10C0.380 (3)0.4063 (17)0.4451 (8)0.050 (4)*
H11A0.005 (3)0.6769 (15)0.4684 (7)0.039 (3)*
H11B0.252 (3)0.7173 (16)0.4176 (8)0.043 (4)*
H11C0.269 (3)0.6146 (19)0.4806 (9)0.059 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0218 (3)0.0241 (3)0.0153 (3)0.0016 (2)0.0035 (2)0.0030 (2)
N20.0250 (3)0.0276 (3)0.0222 (3)0.0009 (2)0.0089 (2)0.0008 (2)
C10.0217 (3)0.0271 (4)0.0188 (3)0.0026 (2)0.0048 (2)0.0028 (2)
C20.0206 (3)0.0298 (4)0.0174 (3)0.0023 (3)0.0035 (2)0.0037 (3)
C30.0199 (3)0.0198 (3)0.0182 (3)0.0007 (2)0.0025 (2)0.0027 (2)
C40.0180 (3)0.0172 (3)0.0168 (3)0.0005 (2)0.0014 (2)0.0011 (2)
C50.0174 (3)0.0177 (3)0.0170 (3)0.0006 (2)0.0005 (2)0.0006 (2)
C60.0170 (3)0.0188 (3)0.0192 (3)0.0011 (2)0.0013 (2)0.0002 (2)
C70.0165 (3)0.0205 (3)0.0168 (3)0.0019 (2)0.0017 (2)0.0008 (2)
C80.0210 (3)0.0187 (3)0.0191 (3)0.0007 (2)0.0018 (2)0.0024 (2)
C90.0209 (3)0.0169 (3)0.0205 (3)0.0015 (2)0.0024 (2)0.0005 (2)
C100.0221 (4)0.0309 (4)0.0287 (4)0.0006 (3)0.0073 (3)0.0057 (3)
C110.0287 (4)0.0371 (5)0.0225 (4)0.0014 (3)0.0078 (3)0.0056 (3)
Geometric parameters (Å, º) top
N1—C31.2744 (10)C5—C61.3831 (10)
N1—C21.4611 (10)C5—H50.983 (14)
N2—C71.3756 (9)C6—C71.4148 (10)
N2—C101.4504 (11)C6—H60.970 (13)
N2—C111.4525 (11)C7—C81.4090 (10)
C1—C1i1.5215 (16)C8—C91.3850 (10)
C1—C21.5275 (12)C8—H80.984 (13)
C1—H1A1.027 (12)C9—H90.935 (13)
C1—H1B1.033 (14)C10—H10A0.981 (14)
C2—H2A0.994 (13)C10—H10B0.977 (14)
C2—H2B0.989 (13)C10—H10C0.972 (16)
C3—C41.4629 (10)C11—H11A0.982 (15)
C3—H30.962 (14)C11—H11B0.988 (15)
C4—C91.3985 (10)C11—H11C0.959 (17)
C4—C51.4007 (10)
C3—N1—C2116.83 (7)C5—C6—C7121.01 (7)
C7—N2—C10119.33 (7)C5—C6—H6119.0 (7)
C7—N2—C11119.29 (7)C7—C6—H6120.0 (7)
C10—N2—C11117.90 (7)N2—C7—C8121.25 (7)
C1i—C1—C2112.54 (8)N2—C7—C6121.36 (7)
C1i—C1—H1A107.8 (7)C8—C7—C6117.38 (6)
C2—C1—H1A109.7 (7)C9—C8—C7120.77 (7)
C1i—C1—H1B106.5 (7)C9—C8—H8116.4 (7)
C2—C1—H1B111.7 (7)C7—C8—H8122.8 (7)
H1A—C1—H1B108.4 (10)C8—C9—C4121.83 (7)
N1—C2—C1110.73 (6)C8—C9—H9118.8 (8)
N1—C2—H2A109.7 (8)C4—C9—H9119.4 (8)
C1—C2—H2A107.6 (7)N2—C10—H10A110.6 (8)
N1—C2—H2B110.8 (7)N2—C10—H10B114.0 (8)
C1—C2—H2B111.4 (8)H10A—C10—H10B108.0 (11)
H2A—C2—H2B106.5 (11)N2—C10—H10C108.1 (9)
N1—C3—C4124.08 (7)H10A—C10—H10C106.3 (12)
N1—C3—H3120.6 (8)H10B—C10—H10C109.5 (12)
C4—C3—H3115.3 (8)N2—C11—H11A112.5 (8)
C9—C4—C5117.49 (6)N2—C11—H11B111.8 (9)
C9—C4—C3119.44 (6)H11A—C11—H11B108.4 (12)
C5—C4—C3123.07 (6)N2—C11—H11C110.1 (11)
C6—C5—C4121.48 (7)H11A—C11—H11C105.1 (13)
C6—C5—H5117.3 (8)H11B—C11—H11C108.7 (13)
C4—C5—H5121.1 (8)
C3—N1—C2—C1146.09 (7)C10—N2—C7—C65.55 (11)
C1i—C1—C2—N162.55 (10)C11—N2—C7—C6164.07 (8)
C2—N1—C3—C4178.83 (7)C5—C6—C7—N2178.02 (7)
N1—C3—C4—C9177.38 (7)C5—C6—C7—C81.14 (11)
N1—C3—C4—C52.61 (12)N2—C7—C8—C9177.21 (7)
C9—C4—C5—C61.36 (11)C6—C7—C8—C91.95 (11)
C3—C4—C5—C6178.63 (7)C7—C8—C9—C41.14 (11)
C4—C5—C6—C70.51 (11)C5—C4—C9—C80.54 (11)
C10—N2—C7—C8175.32 (7)C3—C4—C9—C8179.46 (6)
C11—N2—C7—C816.80 (11)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1ii0.977 (14)2.651 (15)3.5273 (10)149.1 (11)
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC22H30N4
Mr350.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)5.2254 (1), 9.5742 (3), 19.4882 (5)
β (°) 95.512 (1)
V3)970.47 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.57 × 0.31 × 0.19
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.960, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
34188, 4266, 3555
Rint0.038
(sin θ/λ)max1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.148, 1.06
No. of reflections4266
No. of parameters178
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.76, 0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1i0.977 (14)2.651 (15)3.5273 (10)149.1 (11)
Symmetry code: (i) x1, y, z.
 

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