Literature DB >> 22199800

5-Chloro-2-(phenyl-diazen-yl)pyridine.

Steffen Thies, Christian Näther, Rainer Herges.

Abstract

In the title compound, C(11)H(8)ClN(3), the azo group adopts a trans conformation and the dihedral angle between the six-membered rings is 15.47 (8)°.

Entities: Chemical Disease Gene

Year: 2011 PMID： 22199800 PMCID： PMC3238951 DOI： 10.1107/S1600536811047556

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

Related literature

For background to this work, see: Thies et al. (2010 ▶, 2011 ▶); Venkataramani et al. (2011 ▶). For the structure of a bis(5-chloro-2-(phenylazo)pyridine)dichloro–ruthenium(II) complex, see: Hansongnern et al. (2008 ▶).

Experimental

Crystal data

C11H8ClN3 M = 217.65 Monoclinic, a = 6.1136 (2) Å b = 9.0940 (4) Å c = 18.6839 (8) Å β = 91.459 (3)° V = 1038.43 (7) Å3 Z = 4 Mo Kα radiation μ = 0.33 mm−1 T = 293 K 0.3 × 0.2 × 0.2 mm

Data collection

Stoe IPDS-2 diffractometer 19329 measured reflections 2818 independent reflections 2456 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.117 S = 1.15 2818 reflections 137 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.17 e Å−3 Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047556/bt5703sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047556/bt5703Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811047556/bt5703Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₈ClN₃	F(000) = 448
M_r = 217.65	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.1136 (2) Å	Cell parameters from 23258 reflections
b = 9.0940 (4) Å	θ = 2.2–29.2°
c = 18.6839 (8) Å	µ = 0.33 mm⁻¹
β = 91.459 (3)°	T = 293 K
V = 1038.43 (7) Å³	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Stoe IPDS-2 diffractometer	2456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
graphite	θ_max = 29.2°, θ_min = 2.2°
ω scans	h = −7→8
19329 measured reflections	k = −12→12
2818 independent reflections	l = −25→25

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0494P)² + 0.1607P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2818 reflections	Δρ_max = 0.22 e Å⁻³
137 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

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
Cl1	0.82419 (7)	−0.02057 (5)	0.37109 (2)	0.07091 (17)
C1	0.4709 (2)	0.27818 (16)	0.51393 (7)	0.0521 (3)
C2	0.4706 (3)	0.12003 (19)	0.42028 (8)	0.0610 (4)
H2	0.3950	0.0699	0.3840	0.073*
N1	0.3601 (2)	0.20937 (16)	0.46186 (7)	0.0620 (3)
C3	0.6925 (2)	0.09777 (16)	0.42821 (7)	0.0529 (3)
C4	0.8081 (2)	0.17112 (19)	0.48142 (9)	0.0605 (4)
H4	0.9585	0.1591	0.4872	0.073*
C5	0.6949 (2)	0.26232 (18)	0.52564 (8)	0.0586 (4)
H5	0.7666	0.3125	0.5627	0.070*
N2	0.3334 (2)	0.37225 (14)	0.55510 (7)	0.0588 (3)
N3	0.4247 (2)	0.41302 (15)	0.61134 (7)	0.0593 (3)
C6	0.2969 (3)	0.51050 (16)	0.65384 (8)	0.0559 (3)
C7	0.3993 (3)	0.5565 (2)	0.71665 (9)	0.0685 (4)
H7	0.5377	0.5211	0.7292	0.082*
C8	0.2973 (4)	0.6544 (2)	0.76071 (9)	0.0773 (5)
H8	0.3672	0.6861	0.8027	0.093*
C9	0.0916 (4)	0.7056 (2)	0.74256 (10)	0.0778 (5)
H9	0.0224	0.7721	0.7723	0.093*
C10	−0.0123 (3)	0.6581 (2)	0.68026 (11)	0.0750 (5)
H10	−0.1523	0.6919	0.6686	0.090*
C11	0.0890 (3)	0.56153 (19)	0.63543 (9)	0.0626 (4)
H11	0.0192	0.5307	0.5932	0.075*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0752 (3)	0.0732 (3)	0.0646 (3)	0.0099 (2)	0.00810 (19)	−0.00282 (19)
C1	0.0511 (7)	0.0541 (7)	0.0511 (7)	−0.0032 (6)	−0.0005 (6)	0.0062 (6)
C2	0.0545 (8)	0.0704 (9)	0.0577 (8)	−0.0019 (7)	−0.0079 (6)	−0.0056 (7)
N1	0.0487 (6)	0.0749 (8)	0.0619 (7)	0.0003 (6)	−0.0077 (5)	−0.0061 (6)
C3	0.0534 (7)	0.0551 (7)	0.0502 (7)	−0.0004 (6)	0.0027 (6)	0.0077 (6)
C4	0.0429 (7)	0.0727 (9)	0.0658 (9)	−0.0039 (6)	−0.0015 (6)	0.0023 (7)
C5	0.0510 (7)	0.0670 (9)	0.0575 (8)	−0.0113 (6)	−0.0050 (6)	−0.0028 (7)
N2	0.0553 (7)	0.0622 (7)	0.0587 (7)	−0.0034 (6)	−0.0047 (5)	0.0004 (6)
N3	0.0580 (7)	0.0654 (7)	0.0540 (7)	−0.0035 (6)	−0.0044 (5)	0.0024 (6)
C6	0.0605 (8)	0.0544 (8)	0.0529 (7)	−0.0063 (6)	0.0053 (6)	0.0058 (6)
C7	0.0691 (10)	0.0797 (11)	0.0565 (8)	0.0001 (8)	−0.0019 (7)	−0.0023 (8)
C8	0.0968 (14)	0.0797 (12)	0.0554 (9)	−0.0021 (10)	0.0015 (9)	−0.0046 (8)
C9	0.1020 (14)	0.0649 (10)	0.0675 (10)	0.0085 (10)	0.0238 (10)	0.0046 (8)
C10	0.0705 (10)	0.0715 (11)	0.0835 (12)	0.0104 (8)	0.0104 (9)	0.0137 (9)
C11	0.0639 (9)	0.0614 (9)	0.0623 (9)	−0.0049 (7)	−0.0011 (7)	0.0069 (7)

Cl1—C3	1.7288 (15)	N3—C6	1.435 (2)
C1—N1	1.3278 (19)	C6—C7	1.381 (2)
C1—C5	1.389 (2)	C6—C11	1.388 (2)
C1—N2	1.436 (2)	C7—C8	1.373 (3)
C2—N1	1.322 (2)	C7—H7	0.9300
C2—C3	1.376 (2)	C8—C9	1.375 (3)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.377 (2)	C9—C10	1.381 (3)
C4—C5	1.370 (2)	C9—H9	0.9300
C4—H4	0.9300	C10—C11	1.372 (3)
C5—H5	0.9300	C10—H10	0.9300
N2—N3	1.2341 (17)	C11—H11	0.9300

N1—C1—C5	123.29 (15)	C7—C6—C11	120.09 (15)
N1—C1—N2	112.26 (13)	C7—C6—N3	114.62 (14)
C5—C1—N2	124.44 (13)	C11—C6—N3	125.27 (14)
N1—C2—C3	123.00 (14)	C8—C7—C6	120.23 (17)
N1—C2—H2	118.5	C8—C7—H7	119.9
C3—C2—H2	118.5	C6—C7—H7	119.9
C2—N1—C1	117.49 (13)	C7—C8—C9	119.86 (18)
C2—C3—C4	119.51 (14)	C7—C8—H8	120.1
C2—C3—Cl1	119.90 (12)	C9—C8—H8	120.1
C4—C3—Cl1	120.59 (12)	C8—C9—C10	120.02 (18)
C5—C4—C3	118.09 (14)	C8—C9—H9	120.0
C5—C4—H4	121.0	C10—C9—H9	120.0
C3—C4—H4	121.0	C11—C10—C9	120.62 (18)
C4—C5—C1	118.60 (14)	C11—C10—H10	119.7
C4—C5—H5	120.7	C9—C10—H10	119.7
C1—C5—H5	120.7	C10—C11—C6	119.17 (16)
N3—N2—C1	112.15 (13)	C10—C11—H11	120.4
N2—N3—C6	114.60 (13)	C6—C11—H11	120.4

4 in total

1. Coordination-induced spin crossover (CISCO) through axial bonding of substituted pyridines to nickel-porphyrins: sigma-donor versus pi-acceptor effects.

Authors: Steffen Thies; Claudia Bornholdt; Felix Köhler; Frank D Sönnichsen; Christian Näther; Felix Tuczek; Rainer Herges
Journal: Chemistry Date: 2010-09-03 Impact factor: 5.236