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The title compound, C22H20N2, consists of two hypnone groups attached to a benzene ring via two azomethine linkages and crystallizes with an inversion centre at the mid-point of the central benzene ring. Mol­ecules are linked into a chain by C—H...N hydrogen bonds along the b-axis direction. Neighbouring chains are linked by C—H...π hydrogen bonds into sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027754/at2308sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027754/at2308Isup2.hkl
Contains datablock I

CCDC reference: 649511

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.144
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. N1 .. 2.80 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C4 .. N1 .. 97.90 Deg.
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Comment top

As part of our investigation of the reactions between hypnone with diamines, we report here the crystal structure of a hypnone Schiff base, N,N'-bis(3-methoxy-2-hydroxybenzylidene) benzene-1, 4-diamie, (I) and (Fig. 1).

The asymmetric unit consists of one half-molecule. The molecule have an inversion centre at the mid-point of the central benzen ring. The dihedral angle between the neighbouring benzen rings in the molecule is 74.10 (10) °. The bond lengths and angles are normal (Allen et al., 1987) and are in agreement with those in two similar compounds (Xia et al.., 2007; Liu et al., 2006). The molecules are linked into a chain of ring by C—H···N hydrogen bonds. Atom C11 in the molecule (x, y, z) act as hydrogen-bond donor to atom N1 in the molecule (- x, - y, 1 - z), generating a chain of R22(8) rings (Bernstein et al., 1995) along the b-axisdirection (Fig. 2 and Table 1). Neighbouring chains are linked by C—H···π hydrogen bonds into the sheets (Fig. 3) and there are no direction-specific interactions between adjacent sheets.

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Hodnett & Dunn (1970); Liu et al. (2006); Modi et al. (1970); Xia et al. (2007).

Experimental top

Solutions of hypnone (20 mmol) and benzene-1,2-diamie (10 mmol) in benzene (30 ml) was stirred for 6 h and then mixtures was filtered, and then solution was left to produce crystals of (I) slowly.

Refinement top

All H atoms were located in difference Fourier maps. H atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), and Uiso(H) = 1.2Ueq(C) for aryl or 1.5 Ueq(C) for methyl.

Structure description top

As part of our investigation of the reactions between hypnone with diamines, we report here the crystal structure of a hypnone Schiff base, N,N'-bis(3-methoxy-2-hydroxybenzylidene) benzene-1, 4-diamie, (I) and (Fig. 1).

The asymmetric unit consists of one half-molecule. The molecule have an inversion centre at the mid-point of the central benzen ring. The dihedral angle between the neighbouring benzen rings in the molecule is 74.10 (10) °. The bond lengths and angles are normal (Allen et al., 1987) and are in agreement with those in two similar compounds (Xia et al.., 2007; Liu et al., 2006). The molecules are linked into a chain of ring by C—H···N hydrogen bonds. Atom C11 in the molecule (x, y, z) act as hydrogen-bond donor to atom N1 in the molecule (- x, - y, 1 - z), generating a chain of R22(8) rings (Bernstein et al., 1995) along the b-axisdirection (Fig. 2 and Table 1). Neighbouring chains are linked by C—H···π hydrogen bonds into the sheets (Fig. 3) and there are no direction-specific interactions between adjacent sheets.

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Hodnett & Dunn (1970); Liu et al. (2006); Modi et al. (1970); Xia et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. Unlabelled atoms in the molecular are related to labelled atoma by (-x, 1 - y, 1 - z).
[Figure 2] Fig. 2. A larger portion of the crystal struture of (I), the formation of a hydrogen-bonded chain built from C—H···N. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (A) -x, 1 - y, 1 - z; (B) - x, - y, 1 - z; (C) x, 1 + y, z].
[Figure 3] Fig. 3. A larger portion of the crystal struture of (I), the formation of a hydrogen-bonded sheet built from C—H···π. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (A) -x, 1 - y, 1 - z; (B) - x, - y, 1 - z; (C) x, 1 + y, z; (D) 1 - x, 1/2 + y, 1/2 - z; (E) - x, 2 - y, 1 - z; (F) -1 + x, 3/2 - y, 1/2 + z; (G) 1 - x, -1/2 + y, 1/2 - z; (H) -1 + x, 1/2 - y, 1/2 + z].
(6E,7E)-N,N'-Bis(2-hydroxy-3-methoxybenzylidene)benzene-1,4-diamine top
Crystal data top
C22H20N2F(000) = 332
Mr = 312.40Dx = 1.165 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 770 reflections
a = 5.9718 (11) Åθ = 3.1–23.0°
b = 6.8701 (15) ŵ = 0.07 mm1
c = 21.713 (2) ÅT = 298 K
β = 90.720 (2)°Block, colourless
V = 890.8 (3) Å30.45 × 0.42 × 0.19 mm
Z = 2
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1560 independent reflections
Radiation source: fine-focus sealed tube879 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 76
Tmin = 0.970, Tmax = 0.987k = 78
3502 measured reflectionsl = 2519
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.0928P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1560 reflectionsΔρmax = 0.21 e Å3
110 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (5)
Crystal data top
C22H20N2V = 890.8 (3) Å3
Mr = 312.40Z = 2
Monoclinic, P21/cMo Kα radiation
a = 5.9718 (11) ŵ = 0.07 mm1
b = 6.8701 (15) ÅT = 298 K
c = 21.713 (2) Å0.45 × 0.42 × 0.19 mm
β = 90.720 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1560 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
879 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.987Rint = 0.046
3502 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
1560 reflectionsΔρmin = 0.15 e Å3
110 parameters
Special details top

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
N10.1054 (3)0.1888 (3)0.42130 (8)0.0520 (6)
C10.5090 (4)0.2304 (5)0.43650 (14)0.0942 (11)
H1A0.46610.34100.46060.141*
H1B0.60530.27190.40390.141*
H1C0.58710.13860.46230.141*
C20.3038 (4)0.1361 (3)0.40941 (10)0.0466 (6)
C30.3318 (4)0.0279 (3)0.36540 (10)0.0467 (6)
C40.1630 (4)0.0695 (4)0.32348 (11)0.0582 (7)
H40.03260.00450.32340.070*
C50.1853 (5)0.2190 (5)0.28178 (12)0.0774 (9)
H50.07160.24330.25310.093*
C60.3754 (6)0.3328 (5)0.28231 (14)0.0844 (10)
H60.38960.43460.25440.101*
C70.5421 (6)0.2951 (5)0.32399 (15)0.0838 (10)
H70.67000.37230.32490.101*
C80.5219 (4)0.1423 (4)0.36498 (12)0.0671 (8)
H80.63800.11610.39270.080*
C90.0613 (3)0.3471 (3)0.46147 (10)0.0448 (6)
C100.0549 (4)0.5353 (4)0.43993 (11)0.0532 (7)
H100.09030.56040.39910.064*
C110.0035 (4)0.3121 (4)0.52201 (10)0.0523 (7)
H110.00390.18550.53710.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0428 (12)0.0496 (14)0.0636 (13)0.0032 (10)0.0030 (10)0.0110 (10)
C10.0482 (17)0.105 (3)0.129 (3)0.0022 (18)0.0095 (17)0.047 (2)
C20.0404 (14)0.0492 (16)0.0502 (13)0.0039 (12)0.0011 (10)0.0013 (11)
C30.0453 (15)0.0469 (16)0.0481 (13)0.0004 (12)0.0090 (11)0.0030 (11)
C40.0625 (17)0.0571 (18)0.0550 (15)0.0008 (14)0.0014 (12)0.0043 (13)
C50.092 (2)0.076 (2)0.0647 (18)0.0074 (19)0.0038 (15)0.0183 (16)
C60.105 (3)0.074 (2)0.075 (2)0.001 (2)0.0305 (19)0.0197 (17)
C70.084 (2)0.075 (2)0.093 (2)0.0217 (19)0.0296 (19)0.0062 (19)
C80.0564 (17)0.073 (2)0.0722 (18)0.0092 (16)0.0067 (13)0.0050 (15)
C90.0363 (13)0.0415 (15)0.0566 (14)0.0056 (11)0.0001 (10)0.0094 (12)
C100.0581 (16)0.0508 (17)0.0510 (14)0.0081 (13)0.0068 (12)0.0020 (13)
C110.0541 (15)0.0444 (15)0.0586 (16)0.0040 (13)0.0012 (11)0.0009 (12)
Geometric parameters (Å, º) top
N1—C21.268 (3)C5—H50.9300
N1—C91.421 (3)C6—C71.362 (4)
C1—C21.500 (3)C6—H60.9300
C1—H1A0.9600C7—C81.382 (4)
C1—H1B0.9600C7—H70.9300
C1—H1C0.9600C8—H80.9300
C2—C31.489 (3)C9—C101.376 (3)
C3—C41.379 (3)C9—C111.384 (3)
C3—C81.381 (3)C10—C11i1.382 (3)
C4—C51.377 (3)C10—H100.9300
C4—H40.9300C11—C10i1.382 (3)
C5—C61.378 (4)C11—H110.9300
C2—N1—C9121.6 (2)C7—C6—C5119.5 (3)
C2—C1—H1A109.5C7—C6—H6120.2
C2—C1—H1B109.5C5—C6—H6120.2
H1A—C1—H1B109.5C6—C7—C8120.2 (3)
C2—C1—H1C109.5C6—C7—H7119.9
H1A—C1—H1C109.5C8—C7—H7119.9
H1B—C1—H1C109.5C3—C8—C7121.0 (3)
N1—C2—C3117.3 (2)C3—C8—H8119.5
N1—C2—C1123.9 (2)C7—C8—H8119.5
C3—C2—C1118.7 (2)C10—C9—C11118.7 (2)
C4—C3—C8118.2 (2)C10—C9—N1121.0 (2)
C4—C3—C2119.6 (2)C11—C9—N1120.0 (2)
C8—C3—C2122.3 (2)C9—C10—C11i121.0 (2)
C5—C4—C3120.8 (3)C9—C10—H10119.5
C5—C4—H4119.6C11i—C10—H10119.5
C3—C4—H4119.6C10i—C11—C9120.3 (2)
C4—C5—C6120.3 (3)C10i—C11—H11119.9
C4—C5—H5119.9C9—C11—H11119.9
C6—C5—H5119.9
C9—N1—C2—C3178.4 (2)C5—C6—C7—C80.7 (5)
C9—N1—C2—C11.0 (4)C4—C3—C8—C70.4 (4)
N1—C2—C3—C423.3 (3)C2—C3—C8—C7179.3 (2)
C1—C2—C3—C4156.2 (2)C6—C7—C8—C31.3 (4)
N1—C2—C3—C8156.4 (2)C2—N1—C9—C1086.1 (3)
C1—C2—C3—C824.1 (3)C2—N1—C9—C1199.9 (3)
C8—C3—C4—C51.0 (4)C11—C9—C10—C11i1.3 (4)
C2—C3—C4—C5179.3 (2)N1—C9—C10—C11i175.4 (2)
C3—C4—C5—C61.5 (4)C10—C9—C11—C10i1.3 (4)
C4—C5—C6—C70.7 (4)N1—C9—C11—C10i175.4 (2)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N10.932.512.792 (3)98
C11—H11···N1ii0.932.803.715 (3)166
Symmetry code: (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC22H20N2
Mr312.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.9718 (11), 6.8701 (15), 21.713 (2)
β (°) 90.720 (2)
V3)890.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.42 × 0.19
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.970, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
3502, 1560, 879
Rint0.046
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.144, 1.02
No. of reflections1560
No. of parameters110
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.15

Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N10.932.512.792 (3)97.9
C11—H11···N1i0.932.803.715 (3)166.4
Symmetry code: (i) x, y, z+1.
 

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