Literature DB >> 22719496

4-[(E)-(Hy-droxy-imino)-meth-yl]-N,N-di-methyl-anilinium chloride.

T Uma Devi, G Kalpana, S Priya, K Ravikumar, S Selvanayagam.

Abstract

In the title compound, C(9)H(13)N(2)O(+)·Cl(-), the cation, apart from the methyl groups, is almost planar, with a maximum deviation of 0.040 (1) Å; the methyl C atoms deviate by 0.389 (2) and -1.247 (1) Å, from the mean plane. In the crystal, cations and anions associate through C-H⋯Cl hydrogen bonds, forming a helical arrangement. In addition, inter-molecular O-H⋯Cl, N-H⋯Cl and C-H⋯N inter-actions are observed.

Entities: Chemical Disease Species

Year: 2012 PMID： 22719496 PMCID： PMC3379298 DOI： 10.1107/S1600536812020211

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

Related literature

For general background to hydroxylamine derivatives, see: Kataoka et al. (2002 ▶); Haldimann et al. (2011 ▶) and to benzaldehyde derivatives, see: Haraguchi et al. (2011 ▶); Johnston et al. (2011 ▶); Zhang et al. (2011 ▶). For a related structure, see: Bachechi & Zambonelli (1972 ▶).

Experimental

Crystal data

C9H13N2O+·Cl− M = 200.66 Monoclinic, a = 11.2696 (10) Å b = 11.7093 (10) Å c = 7.6961 (7) Å β = 90.108 (2)° V = 1015.57 (16) Å3 Z = 4 Mo Kα radiation μ = 0.34 mm−1 T = 292 K 0.24 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer 11453 measured reflections 2405 independent reflections 2240 reflections with I > 2σigma(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.093 S = 1.07 2405 reflections 125 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.20 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020211/zq2166sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020211/zq2166Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812020211/zq2166Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₉H₁₃N₂O⁺·Cl⁻	F(000) = 424
M_r = 200.66	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7257 reflections
a = 11.2696 (10) Å	θ = 2.3–26.6°
b = 11.7093 (10) Å	µ = 0.34 mm⁻¹
c = 7.6961 (7) Å	T = 292 K
β = 90.108 (2)°	Needle, brown
V = 1015.57 (16) Å³	0.24 × 0.20 × 0.19 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2240 reflections with I > 2σigma(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 28.0°, θ_min = 1.8°
ω scans	h = −14→14
11453 measured reflections	k = −15→15
2405 independent reflections	l = −9→10

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0536P)² + 0.1829P] where P = (F_o² + 2F_c²)/3
2405 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.16123 (3)	0.02780 (2)	0.86101 (4)	0.04216 (12)
O1	0.81494 (8)	0.28038 (8)	0.48301 (14)	0.0490 (2)
H1	0.8321	0.3407	0.5309	0.073*
N1	0.17646 (8)	0.07318 (8)	0.24932 (13)	0.0370 (2)
H1N	0.1744 (14)	0.0531 (13)	0.1354 (18)	0.050 (4)*
N2	0.69124 (9)	0.27159 (9)	0.46814 (14)	0.0405 (2)
C1	0.30082 (10)	0.10295 (10)	0.29034 (14)	0.0354 (2)
C2	0.32816 (11)	0.20083 (11)	0.38181 (18)	0.0472 (3)
H2	0.2683	0.2494	0.4197	0.057*
C3	0.44580 (11)	0.22569 (11)	0.41636 (18)	0.0471 (3)
H3	0.4647	0.2913	0.4787	0.057*
C4	0.53633 (10)	0.15418 (9)	0.35930 (14)	0.0351 (2)
C5	0.50650 (11)	0.05628 (10)	0.26681 (16)	0.0395 (3)
H5	0.5661	0.0076	0.2283	0.047*
C6	0.38908 (11)	0.03048 (9)	0.23151 (16)	0.0400 (3)
H6	0.3697	−0.0349	0.1689	0.048*
C7	0.66167 (10)	0.18062 (10)	0.38936 (15)	0.0370 (2)
H7	0.7199	0.1305	0.3506	0.044*
C8	0.08882 (12)	0.16749 (13)	0.2724 (2)	0.0568 (4)
H8A	0.0145	0.1459	0.2209	0.085*
H8B	0.1179	0.2354	0.2172	0.085*
H8C	0.0776	0.1818	0.3941	0.085*
C9	0.13654 (13)	−0.03099 (11)	0.34631 (19)	0.0494 (3)
H9A	0.1896	−0.0931	0.3223	0.074*
H9B	0.0577	−0.0512	0.3100	0.074*
H9C	0.1367	−0.0154	0.4688	0.074*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.04579 (19)	0.03872 (18)	0.04194 (19)	0.00255 (10)	−0.00722 (12)	−0.00218 (10)
O1	0.0383 (5)	0.0437 (5)	0.0649 (6)	−0.0055 (3)	−0.0106 (4)	−0.0029 (4)
N1	0.0367 (5)	0.0376 (5)	0.0367 (5)	−0.0020 (4)	−0.0068 (4)	−0.0022 (4)
N2	0.0368 (5)	0.0381 (5)	0.0467 (5)	−0.0010 (4)	−0.0075 (4)	0.0001 (4)
C1	0.0351 (5)	0.0366 (5)	0.0344 (5)	−0.0020 (4)	−0.0050 (4)	−0.0021 (4)
C2	0.0380 (6)	0.0472 (7)	0.0564 (7)	0.0046 (5)	−0.0034 (5)	−0.0200 (6)
C3	0.0412 (6)	0.0445 (6)	0.0555 (7)	0.0002 (5)	−0.0067 (5)	−0.0213 (6)
C4	0.0376 (5)	0.0343 (5)	0.0334 (5)	0.0002 (4)	−0.0050 (4)	−0.0008 (4)
C5	0.0393 (6)	0.0339 (5)	0.0453 (6)	0.0036 (4)	−0.0021 (5)	−0.0059 (5)
C6	0.0425 (6)	0.0324 (5)	0.0450 (6)	−0.0012 (4)	−0.0047 (5)	−0.0089 (4)
C7	0.0371 (6)	0.0359 (5)	0.0379 (5)	0.0022 (4)	−0.0046 (4)	−0.0004 (4)
C8	0.0409 (7)	0.0507 (7)	0.0786 (10)	0.0058 (6)	−0.0136 (6)	−0.0133 (7)
C9	0.0463 (7)	0.0514 (8)	0.0506 (7)	−0.0096 (5)	−0.0054 (6)	0.0100 (5)

O1—N2	1.4023 (13)	C4—C5	1.3903 (16)
O1—H1	0.8200	C4—C7	1.4640 (15)
N1—C1	1.4777 (14)	C5—C6	1.3838 (17)
N1—C8	1.4924 (17)	C5—H5	0.9300
N1—C9	1.4995 (16)	C6—H6	0.9300
N1—H1N	0.908 (13)	C7—H7	0.9300
N2—C7	1.2698 (15)	C8—H8A	0.9600
C1—C2	1.3796 (16)	C8—H8B	0.9600
C1—C6	1.3842 (16)	C8—H8C	0.9600
C2—C3	1.3827 (18)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—C4	1.3916 (17)	C9—H9C	0.9600
C3—H3	0.9300

N2—O1—H1	109.5	C6—C5—H5	119.6
C1—N1—C8	115.32 (9)	C4—C5—H5	119.6
C1—N1—C9	111.77 (9)	C5—C6—C1	119.30 (10)
C8—N1—C9	110.08 (11)	C5—C6—H6	120.4
C1—N1—H1N	106.8 (10)	C1—C6—H6	120.4
C8—N1—H1N	106.9 (10)	N2—C7—C4	120.34 (11)
C9—N1—H1N	105.3 (10)	N2—C7—H7	119.8
C7—N2—O1	111.13 (10)	C4—C7—H7	119.8
C2—C1—C6	121.09 (11)	N1—C8—H8A	109.5
C2—C1—N1	121.05 (10)	N1—C8—H8B	109.5
C6—C1—N1	117.86 (10)	H8A—C8—H8B	109.5
C1—C2—C3	119.09 (11)	N1—C8—H8C	109.5
C1—C2—H2	120.5	H8A—C8—H8C	109.5
C3—C2—H2	120.5	H8B—C8—H8C	109.5
C2—C3—C4	121.06 (11)	N1—C9—H9A	109.5
C2—C3—H3	119.5	N1—C9—H9B	109.5
C4—C3—H3	119.5	H9A—C9—H9B	109.5
C5—C4—C3	118.75 (11)	N1—C9—H9C	109.5
C5—C4—C7	119.18 (10)	H9A—C9—H9C	109.5
C3—C4—C7	122.05 (10)	H9B—C9—H9C	109.5
C6—C5—C4	120.72 (11)

C8—N1—C1—C2	14.77 (17)	C3—C4—C5—C6	0.22 (18)
C9—N1—C1—C2	−111.95 (13)	C7—C4—C5—C6	−178.05 (11)
C8—N1—C1—C6	−164.17 (12)	C4—C5—C6—C1	−0.43 (19)
C9—N1—C1—C6	69.11 (14)	C2—C1—C6—C5	0.67 (19)
C6—C1—C2—C3	−0.7 (2)	N1—C1—C6—C5	179.61 (11)
N1—C1—C2—C3	−179.60 (12)	O1—N2—C7—C4	−179.96 (10)
C1—C2—C3—C4	0.5 (2)	C5—C4—C7—N2	177.52 (11)
C2—C3—C4—C5	−0.2 (2)	C3—C4—C7—N2	−0.69 (18)
C2—C3—C4—C7	177.96 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1ⁱ	0.82	2.34	3.147 (1)	167
N1—H1N···Cl1ⁱⁱ	0.91 (1)	2.14 (1)	3.040 (1)	173 (1)
C6—H6···N2ⁱⁱⁱ	0.93	2.59	3.516 (2)	173
C7—H7···Cl1^iv	0.93	2.81	3.697 (1)	160
C9—H9B···Cl1^v	0.96	2.81	3.713 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1ⁱ	0.82	2.34	3.147 (1)	167
N1—H1N⋯Cl1ⁱⁱ	0.91 (1)	2.14 (1)	3.040 (1)	173 (1)
C6—H6⋯N2ⁱⁱⁱ	0.93	2.59	3.516 (2)	173
C7—H7⋯Cl1^iv	0.93	2.81	3.697 (1)	160
C9—H9B⋯Cl1^v	0.96	2.81	3.713 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

7 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Anti-inflammatory and anti-allergic activities of hydroxylamine and related compounds.

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Journal: Biol Pharm Bull Date: 2002-11 Impact factor: 2.233

3. Preparation and characterization of new and improved soluble-starches, -amylose, and -amylopectin by reaction with benzaldehyde/zinc chloride.

Authors: David A Johnston; Rupendra Mukerjea; John F Robyt
Journal: Carbohydr Res Date: 2011-10-08 Impact factor: 2.104

4. Synthesis, antibacterial activities and molecular docking studies of Schiff bases derived from N-(2/4-benzaldehyde-amino) phenyl-N'-phenyl-thiourea.

Authors: Hong-Jia Zhang; Xuan Qin; Kai Liu; Di-Di Zhu; Xiao-Ming Wang; Hai-Liang Zhu
Journal: Bioorg Med Chem Date: 2011-07-01 Impact factor: 3.641