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The mol­ecule of the title Schiff base compound, C17H16N4O4, has crystallographic twofold rotation symmetry. The nitro and CH=N—C substituents are coplanar with the benzene ring in each half of the mol­ecule. These two planar units are parallel, but extend in opposite directions from the central methyl­ene bridge, so there is no intra­molecular π-stacking. Instead, mol­ecules pack with approximately parallel inter­leaved benzene rings providing inter­molecular π-stacking, the centroid-to-centroid separation being 3.7196 (18) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021940/xu2251sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021940/xu2251Isup2.hkl
Contains datablock I

CCDC reference: 602592

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.104
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1004 Count of symmetry unique reflns 1010 Completeness (_total/calc) 99.41% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff base compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and molecular architectures. Structures of Schiff bases derived from nitrobenzaldehydes and closely related to the title compound have been reported by Li et al. (2005), Bomfin et al. (2005), Glidewell et al. (2005, 2006), and Sun et al. (2004).

The title compound, (I), was prepared by the condensation of 3-nitrobenzaldehyde and 1,3-diaminopropane in a 2:1 molar ratio. A view of the molecular structure is shown in Fig. 1. The molecule has crystallographic twofold rotation symmetry. Bond lengths and angles are unexceptional. The nitro and CHN—C substituents are coplanar with the benzene ring in each half of the molecule. These two planar units are parallel by symmetry, but extend in opposite directions from the central methylene bridge, so there is no intramolecular π-stacking. Instead, molecules pack with approximately parallel interleaved benzene rings providing intermolecular π-stacking, the centroid-to-centroid separation being 3.7196 (18) Å (Fig. 2).

Related literature top

For related structures, see: Li et al. (2005), Bomfin et al. (2005), Glidewell et al. (2005, 2006), and Sun et al., (2004).

Experimental top

A solution of 1,3-propanediamine (0.1 mmol, 0.074 g) in chloroform (5 ml) was slowly added to a solution of 3-nitrobenzaldehyde (0.2 mmol, 0.30 g) in the same solvent (5 ml). Recrystallization of the resulting solid from ethanol afforded colourless crystals, 81% yield.

Refinement top

Hydrogen atoms were positioned geometrically with C—H = 0.95 (aromatic) or 0.98 Å (CH2), and refined in riding mode with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Structure description top

Schiff base compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and molecular architectures. Structures of Schiff bases derived from nitrobenzaldehydes and closely related to the title compound have been reported by Li et al. (2005), Bomfin et al. (2005), Glidewell et al. (2005, 2006), and Sun et al. (2004).

The title compound, (I), was prepared by the condensation of 3-nitrobenzaldehyde and 1,3-diaminopropane in a 2:1 molar ratio. A view of the molecular structure is shown in Fig. 1. The molecule has crystallographic twofold rotation symmetry. Bond lengths and angles are unexceptional. The nitro and CHN—C substituents are coplanar with the benzene ring in each half of the molecule. These two planar units are parallel by symmetry, but extend in opposite directions from the central methylene bridge, so there is no intramolecular π-stacking. Instead, molecules pack with approximately parallel interleaved benzene rings providing intermolecular π-stacking, the centroid-to-centroid separation being 3.7196 (18) Å (Fig. 2).

For related structures, see: Li et al. (2005), Bomfin et al. (2005), Glidewell et al. (2005, 2006), and Sun et al., (2004).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Sheldrick, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure with atom labels and 50% probability ellipsoids for non-H atoms [symmetry code for unlabelled atoms: -x, -y, z].
[Figure 2] Fig. 2. The packing, viewed down the c axis, showing stacking of the benzene rings.
N,N'-bis(3-nitrobenzylidene)propane-1,3-diamine top
Crystal data top
C17H16N4O4Dx = 1.390 Mg m3
Mr = 340.34Melting point: 390 K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 106 reflections
a = 12.994 (3) Åθ = 2.5–27.5°
b = 35.859 (12) ŵ = 0.10 mm1
c = 6.983 (2) ÅT = 150 K
V = 3253.7 (16) Å3Block, colourless
Z = 80.45 × 0.40 × 0.40 mm
F(000) = 1424
Data collection top
Nonius KappaCCD
diffractometer
858 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.038
Graphite monochromatorθmax = 27.5°, θmin = 4.3°
φ and ω scansh = 1611
7631 measured reflectionsk = 4646
1004 independent reflectionsl = 79
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0609P)2 + 1.1167P]
where P = (Fo2 + 2Fc2)/3
1004 reflections(Δ/σ)max < 0.001
114 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = 0.23 e Å3
Crystal data top
C17H16N4O4V = 3253.7 (16) Å3
Mr = 340.34Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 12.994 (3) ŵ = 0.10 mm1
b = 35.859 (12) ÅT = 150 K
c = 6.983 (2) Å0.45 × 0.40 × 0.40 mm
Data collection top
Nonius KappaCCD
diffractometer
858 reflections with I > 2σ(I)
7631 measured reflectionsRint = 0.038
1004 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.104H-atom parameters constrained
S = 1.15Δρmax = 0.26 e Å3
1004 reflectionsΔρmin = 0.23 e Å3
114 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.06407 (16)0.18127 (4)0.6914 (3)0.0409 (5)
O20.09163 (14)0.21456 (5)0.4384 (3)0.0446 (5)
N10.08005 (15)0.18443 (5)0.5184 (3)0.0304 (5)
N20.09255 (14)0.04422 (5)0.6668 (3)0.0310 (5)
C10.08638 (15)0.15000 (6)0.4017 (3)0.0249 (5)
C20.09912 (17)0.15330 (7)0.2039 (4)0.0298 (5)
H20.10140.17700.14350.036*
C30.10824 (18)0.12071 (7)0.0994 (4)0.0349 (6)
H30.11620.12190.03570.042*
C40.10585 (17)0.08602 (7)0.1900 (3)0.0308 (6)
H40.11300.06390.11610.037*
C50.09300 (15)0.08339 (6)0.3882 (3)0.0259 (6)
C60.08196 (16)0.11602 (6)0.4955 (3)0.0226 (5)
H60.07160.11490.63000.027*
C70.09518 (17)0.04671 (6)0.4865 (4)0.0296 (6)
H70.09860.02460.41200.036*
C80.09691 (18)0.00688 (6)0.7532 (4)0.0324 (6)
H8A0.15850.00490.83610.039*
H8B0.10240.01220.65120.039*
C90.00000.00000.8718 (5)0.0292 (7)
H9A0.01180.02190.95550.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0569 (11)0.0346 (9)0.0313 (11)0.0037 (8)0.0078 (9)0.0082 (8)
O20.0501 (11)0.0270 (9)0.0566 (14)0.0030 (7)0.0149 (10)0.0076 (9)
N10.0243 (10)0.0299 (11)0.0369 (13)0.0018 (7)0.0044 (9)0.0007 (9)
N20.0316 (11)0.0238 (9)0.0377 (12)0.0004 (7)0.0007 (9)0.0014 (8)
C10.0178 (10)0.0302 (12)0.0267 (14)0.0016 (8)0.0022 (9)0.0004 (9)
C20.0232 (11)0.0400 (12)0.0263 (14)0.0040 (9)0.0006 (10)0.0074 (11)
C30.0256 (13)0.0613 (18)0.0180 (12)0.0071 (10)0.0023 (10)0.0008 (12)
C40.0236 (11)0.0436 (13)0.0253 (14)0.0042 (9)0.0002 (10)0.0100 (11)
C50.0192 (11)0.0313 (12)0.0272 (15)0.0031 (8)0.0023 (9)0.0041 (9)
C60.0190 (11)0.0298 (11)0.0191 (12)0.0019 (8)0.0002 (9)0.0006 (9)
C70.0257 (12)0.0268 (11)0.0364 (15)0.0028 (8)0.0032 (10)0.0082 (10)
C80.0335 (12)0.0225 (11)0.0412 (15)0.0024 (9)0.0012 (11)0.0017 (10)
C90.0288 (16)0.0238 (14)0.0350 (18)0.0029 (12)0.0000.000
Geometric parameters (Å, º) top
O1—N11.231 (3)C4—C51.397 (3)
O2—N11.226 (3)C5—C61.397 (3)
N1—C11.482 (3)C5—C71.484 (3)
N2—C71.263 (4)C6—H60.950
N2—C81.470 (3)C7—H70.950
C1—C21.396 (4)C8—H8A0.990
C1—C61.384 (3)C8—H8B0.990
C2—H20.950C8—C91.527 (3)
C2—C31.383 (3)C9—C8i1.527 (3)
C3—H30.950C9—H9A0.990
C3—C41.396 (4)C9—H9Ai0.990
C4—H40.950
O1—N1—O2123.3 (2)C1—C6—C5118.6 (2)
O1—N1—C1118.20 (19)C1—C6—H6120.7
O2—N1—C1118.5 (2)C5—C6—H6120.7
C7—N2—C8118.2 (2)N2—C7—C5121.6 (2)
N1—C1—C2118.7 (2)N2—C7—H7119.2
N1—C1—C6118.1 (2)C5—C7—H7119.2
C2—C1—C6123.2 (2)N2—C8—H8A109.7
C1—C2—H2121.3N2—C8—H8B109.7
C1—C2—C3117.4 (2)N2—C8—C9109.75 (16)
H2—C2—C3121.3H8A—C8—H8B108.2
C2—C3—H3119.6H8A—C8—C9109.7
C2—C3—C4120.8 (2)H8B—C8—C9109.7
H3—C3—C4119.6C8—C9—C8i114.3 (3)
C3—C4—H4119.6C8—C9—H9A108.7
C3—C4—C5120.8 (2)C8i—C9—H9A108.7
H4—C4—C5119.6C8—C9—H9Ai108.7
C4—C5—C6119.1 (2)C8i—C9—H9Ai108.7
C4—C5—C7121.0 (2)H9A—C9—H9Ai107.6
C6—C5—C7119.8 (2)
O1—N1—C1—C2176.7 (2)N1—C1—C6—C5176.85 (18)
O1—N1—C1—C64.9 (3)C2—C1—C6—C51.4 (3)
O2—N1—C1—C23.8 (3)C4—C5—C6—C11.4 (3)
O2—N1—C1—C6174.61 (18)C7—C5—C6—C1176.16 (18)
N1—C1—C2—C3177.89 (19)C8—N2—C7—C5178.89 (18)
C6—C1—C2—C30.4 (3)C4—C5—C7—N2173.8 (2)
C1—C2—C3—C40.7 (3)C6—C5—C7—N23.7 (3)
C2—C3—C4—C50.7 (3)C7—N2—C8—C9120.0 (2)
C3—C4—C5—C60.3 (3)N2—C8—C9—C8i73.30 (18)
C3—C4—C5—C7177.17 (19)
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC17H16N4O4
Mr340.34
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)150
a, b, c (Å)12.994 (3), 35.859 (12), 6.983 (2)
V3)3253.7 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.45 × 0.40 × 0.40
Data collection
DiffractometerNonius KappaCCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7631, 1004, 858
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.104, 1.15
No. of reflections1004
No. of parameters114
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.23

Computer programs: COLLECT (Nonius, 1998), EVALCCD (Duisenberg et al., 2003), EVALCCD, SHELXTL (Sheldrick, 2005), SHELXTL and local programs.

 

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