Literature DB >> 21581898

1,4-Bis(2-pyridylmethyl-eneamino-meth-yl)benzene.

Chao Li¹, Fu-An Sun, Ming-Yang He, Huan Xu, Qun Chen.

Abstract

The asymmetric unit of the centrosymmetric title compound, C(20)H(18)N(4), contains one half-mol-ecule. The pyridine and benzene rings are oriented at a dihedral angle of 77.21 (7)°.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21581898 PMCID： PMC2968250 DOI： 10.1107/S1600536809000646

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background, see: Barboiu et al. (2006 ▶); Keegan et al. (2002 ▶); Yue et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H18N4 M = 314.38 Triclinic, a = 4.527 (3) Å b = 10.117 (6) Å c = 10.456 (6) Å α = 61.086 (7)° β = 88.543 (8)° γ = 82.242 (8)° V = 414.9 (4) Å3 Z = 1 Mo Kα radiation μ = 0.08 mm−1 T = 296 (2) K 0.32 × 0.30 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.976, T max = 0.990 2909 measured reflections 1449 independent reflections 1250 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.105 S = 1.01 1449 reflections 109 parameters H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.18 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000646/hk2592sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000646/hk2592Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₀H₁₈N₄	Z = 1
M_r = 314.38	F(000) = 166
Triclinic, P1	D_x = 1.258 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.527 (3) Å	Cell parameters from 1582 reflections
b = 10.117 (6) Å	θ = 2.2–27.0°
c = 10.456 (6) Å	µ = 0.08 mm⁻¹
α = 61.086 (7)°	T = 296 K
β = 88.543 (8)°	Block, colorless
γ = 82.242 (8)°	0.32 × 0.30 × 0.23 mm
V = 414.9 (4) Å³

Bruker SMART CCD area-detector diffractometer	1449 independent reflections
Radiation source: fine-focus sealed tube	1250 reflections with I > 2σ(I)
graphite	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −5→5
T_min = 0.976, T_max = 0.990	k = −12→12
2909 measured reflections	l = −12→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0501P] where P = (F_o² + 2F_c²)/3
1449 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

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	U_iso*/U_eq
N1	0.8015 (3)	0.26368 (14)	1.18773 (13)	0.0628 (3)
N2	0.4321 (2)	0.26607 (12)	0.89307 (11)	0.0516 (3)
C1	0.7265 (3)	0.20335 (14)	1.10637 (13)	0.0477 (3)
C2	0.8567 (3)	0.06149 (15)	1.12895 (14)	0.0536 (3)
H2	0.7948	0.0215	1.0722	0.064*
C3	1.0786 (3)	−0.01952 (17)	1.23630 (16)	0.0622 (4)
H3	1.1727	−0.1140	1.2519	0.075*
C4	1.1584 (4)	0.04142 (19)	1.31980 (16)	0.0673 (4)
H4	1.3071	−0.0110	1.3937	0.081*
C5	1.0143 (4)	0.18146 (19)	1.29230 (17)	0.0714 (5)
H5	1.0687	0.2215	1.3503	0.086*
C6	0.4970 (3)	0.29926 (14)	0.98916 (14)	0.0497 (3)
H6	0.3968	0.3873	0.9862	0.060*
C7	0.2103 (3)	0.37330 (16)	0.77804 (14)	0.0560 (4)
H7A	0.1281	0.4543	0.7986	0.067*
H7B	0.0484	0.3210	0.7748	0.067*
C8	0.3559 (3)	0.43975 (14)	0.63283 (13)	0.0470 (3)
C9	0.3629 (3)	0.37288 (15)	0.54431 (14)	0.0541 (3)
H9	0.2705	0.2866	0.5733	0.065*
C10	0.4953 (3)	0.56793 (15)	0.58621 (14)	0.0544 (4)
H10	0.4935	0.6150	0.6438	0.065*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0703 (8)	0.0659 (7)	0.0620 (7)	−0.0068 (6)	−0.0016 (6)	−0.0391 (6)
N2	0.0562 (7)	0.0502 (6)	0.0452 (6)	−0.0045 (5)	0.0029 (5)	−0.0215 (5)
C1	0.0499 (7)	0.0519 (7)	0.0441 (7)	−0.0121 (6)	0.0107 (5)	−0.0246 (6)
C2	0.0571 (8)	0.0527 (7)	0.0524 (7)	−0.0080 (6)	0.0060 (6)	−0.0268 (6)
C3	0.0614 (9)	0.0552 (8)	0.0598 (8)	−0.0025 (6)	0.0032 (7)	−0.0214 (7)
C4	0.0614 (9)	0.0776 (10)	0.0520 (8)	−0.0078 (8)	−0.0027 (7)	−0.0231 (8)
C5	0.0784 (11)	0.0846 (11)	0.0626 (9)	−0.0120 (9)	−0.0046 (8)	−0.0441 (9)
C6	0.0521 (7)	0.0461 (7)	0.0512 (7)	−0.0057 (5)	0.0079 (6)	−0.0245 (6)
C7	0.0507 (8)	0.0607 (8)	0.0542 (8)	−0.0029 (6)	0.0009 (6)	−0.0271 (7)
C8	0.0393 (6)	0.0488 (7)	0.0470 (7)	0.0033 (5)	−0.0071 (5)	−0.0206 (6)
C9	0.0563 (8)	0.0498 (7)	0.0571 (8)	−0.0099 (6)	−0.0004 (6)	−0.0258 (6)
C10	0.0593 (8)	0.0566 (8)	0.0539 (8)	−0.0048 (6)	−0.0020 (6)	−0.0326 (6)

N1—C1	1.3358 (17)	C6—C1	1.472 (2)
N1—C5	1.332 (2)	C6—H6	0.9300
N2—C6	1.2555 (17)	C7—H7A	0.9700
N2—C7	1.4620 (18)	C7—H7B	0.9700
C1—C2	1.383 (2)	C8—C7	1.5078 (19)
C2—C3	1.373 (2)	C8—C9	1.3832 (19)
C2—H2	0.9300	C8—C10	1.383 (2)
C3—C4	1.367 (2)	C9—C10ⁱ	1.379 (2)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.372 (2)	C10—C9ⁱ	1.379 (2)
C4—H4	0.9300	C10—H10	0.9300
C5—H5	0.9300

C5—N1—C1	116.79 (13)	N2—C6—H6	118.9
C6—N2—C7	117.39 (12)	C1—C6—H6	118.9
N1—C1—C2	122.69 (13)	N2—C7—C8	109.34 (11)
N1—C1—C6	115.30 (12)	N2—C7—H7A	109.8
C2—C1—C6	122.01 (12)	C8—C7—H7A	109.8
C3—C2—C1	119.09 (13)	N2—C7—H7B	109.8
C3—C2—H2	120.5	C8—C7—H7B	109.8
C1—C2—H2	120.5	H7A—C7—H7B	108.3
C4—C3—C2	118.73 (14)	C9—C8—C7	121.61 (12)
C4—C3—H3	120.6	C10—C8—C7	120.48 (11)
C2—C3—H3	120.6	C10ⁱ—C9—C8	121.07 (13)
C3—C4—C5	118.57 (14)	C10—C8—C9	117.88 (12)
C3—C4—H4	120.7	C10ⁱ—C9—H9	119.5
C5—C4—H4	120.7	C8—C9—H9	119.5
N1—C5—C4	124.10 (14)	C9ⁱ—C10—C8	121.05 (12)
N1—C5—H5	117.9	C9ⁱ—C10—H10	119.5
C4—C5—H5	117.9	C8—C10—H10	119.5
N2—C6—C1	122.13 (12)

C5—N1—C1—C2	1.0 (2)	C3—C4—C5—N1	−0.7 (2)
C5—N1—C1—C6	−178.28 (12)	N2—C6—C1—N1	170.79 (11)
C1—N1—C5—C4	0.3 (2)	N2—C6—C1—C2	−8.52 (19)
C7—N2—C6—C1	−177.26 (11)	C9—C8—C7—N2	90.82 (14)
C6—N2—C7—C8	115.21 (13)	C10—C8—C7—N2	−87.19 (15)
N1—C1—C2—C3	−2.0 (2)	C7—C8—C9—C10ⁱ	−178.00 (12)
C6—C1—C2—C3	177.27 (11)	C10—C8—C9—C10ⁱ	0.1 (2)
C1—C2—C3—C4	1.6 (2)	C7—C8—C10—C9ⁱ	178.03 (12)
C2—C3—C4—C5	−0.3 (2)	C9—C8—C10—C9ⁱ	−0.1 (2)

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