Literature DB >> 21582167

4-(4-Methoxy-phen-yl)piperazin-1-ium chloride.

M Nawaz Tahir, Muhammad Danish, Niaz Muhammad, Saqib Ali.

Abstract

In the title compound, C(11)H(17)N(2)O(+)·Cl(-), the dihedral angle between the benzene ring and the basal plane of piperazine ring is 39.20 (8)°. In the crystal, intermolecular N-H⋯Cl hydrogen bonds occur. There is also a C-H⋯π inter-action between the benzene rings.

Entities: CellLine Chemical Disease Gene

Year: 2009 PMID： 21582167 PMCID： PMC2968517 DOI： 10.1107/S1600536809004280

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

Related literature

The title compound was obtained as a by-product in a continuation of work on the synthesis of tin complexes containing piperazine, see: Zia-ur-Rahman et al. (2006 ▶, 2007 ▶). For related structures, see: Lu (2007 ▶); Sadiq-ur-Rehman et al. (2007 ▶).

Experimental

Crystal data

C11H17N2O+·Cl− M = 228.72 Orthorhombic, a = 10.2890 (7) Å b = 31.5218 (18) Å c = 7.5909 (5) Å V = 2461.9 (3) Å3 Z = 8 Mo Kα radiation μ = 0.29 mm−1 T = 296 (2) K 0.28 × 0.22 × 0.15 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.922, T max = 0.950 7605 measured reflections 3073 independent reflections 2327 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.139 S = 1.01 3073 reflections 137 parameters 1 restraint H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.29 e Å−3 Absolute structure: Flack (1983 ▶), 1076 Friedel pairs Flack parameter: 0.05 (9) Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004280/at2720sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004280/at2720Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₁₇N₂O⁺·Cl⁻	F(000) = 976
M_r = 228.72	D_x = 1.234 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 3073 reflections
a = 10.2890 (7) Å	θ = 1.2–30.5°
b = 31.5218 (18) Å	µ = 0.29 mm⁻¹
c = 7.5909 (5) Å	T = 296 K
V = 2461.9 (3) Å³	Prismatic, colourless
Z = 8	0.28 × 0.22 × 0.15 mm

Bruker KAPPA APEXII CCD diffractometer	3073 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
graphite	R_int = 0.026
Detector resolution: 7.3 pixels mm^-1	θ_max = 30.5°, θ_min = 1.3°
ω scans	h = −14→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −42→44
T_min = 0.922, T_max = 0.950	l = −5→10
7605 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0883P)² + 0.0737P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.139	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.35 e Å⁻³
3073 reflections	Δρ_min = −0.29 e Å⁻³
137 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0136 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1076 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.05 (9)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.41690 (13)	0.30736 (4)	0.7357 (3)	0.0454 (4)
N1	0.30676 (15)	0.13295 (5)	0.7320 (3)	0.0407 (5)
N2	0.25384 (18)	0.04631 (6)	0.6512 (4)	0.0561 (8)
C1	0.33328 (16)	0.17757 (5)	0.7214 (3)	0.0334 (5)
C2	0.25085 (17)	0.20603 (6)	0.6364 (3)	0.0368 (6)
C3	0.27578 (17)	0.24960 (7)	0.6389 (3)	0.0362 (6)
C4	0.38456 (16)	0.26505 (6)	0.7235 (3)	0.0329 (5)
C5	0.46885 (18)	0.23669 (6)	0.8075 (3)	0.0371 (5)
C6	0.44271 (18)	0.19397 (6)	0.8060 (3)	0.0386 (6)
C7	0.3309 (3)	0.33675 (8)	0.6540 (4)	0.0641 (9)
C8	0.1772 (2)	0.11964 (7)	0.6751 (3)	0.0486 (7)
C9	0.1533 (2)	0.07386 (7)	0.7291 (4)	0.0563 (7)
C10	0.3855 (3)	0.06000 (7)	0.7054 (4)	0.0617 (9)
C11	0.4071 (2)	0.10588 (7)	0.6540 (4)	0.0513 (7)
Cl1	0.24567 (7)	0.04913 (2)	0.23863 (13)	0.0710 (3)
H2	0.17815	0.19587	0.57701	0.0442*
H2A	0.24059	0.01935	0.68585	0.0673*
H2B	0.24770	0.04718	0.53299	0.0673*
H3	0.21888	0.26823	0.58342	0.0435*
H5	0.54265	0.24678	0.86451	0.0446*
H6	0.49937	0.17549	0.86277	0.0464*
H7A	0.36281	0.36507	0.67113	0.0962*
H7B	0.32577	0.33080	0.53014	0.0962*
H7C	0.24605	0.33421	0.70556	0.0962*
H8A	0.11208	0.13783	0.72828	0.0583*
H8B	0.17019	0.12226	0.54811	0.0583*
H9A	0.06804	0.06493	0.68906	0.0675*
H9B	0.15557	0.07151	0.85649	0.0675*
H10A	0.39486	0.05691	0.83195	0.0742*
H10B	0.45021	0.04222	0.64893	0.0742*
H11A	0.40474	0.10852	0.52670	0.0615*
H11B	0.49212	0.11503	0.69420	0.0615*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0468 (7)	0.0384 (7)	0.0510 (9)	−0.0060 (5)	−0.0035 (8)	0.0000 (8)
N1	0.0415 (8)	0.0359 (7)	0.0447 (9)	0.0009 (6)	0.0001 (9)	0.0004 (8)
N2	0.0814 (15)	0.0327 (10)	0.0542 (14)	−0.0018 (8)	−0.0042 (10)	0.0048 (9)
C1	0.0351 (8)	0.0346 (8)	0.0306 (9)	0.0019 (6)	0.0006 (9)	−0.0009 (8)
C2	0.0353 (9)	0.0401 (10)	0.0351 (11)	−0.0007 (7)	−0.0065 (8)	0.0002 (8)
C3	0.0345 (9)	0.0382 (10)	0.0359 (10)	0.0024 (7)	−0.0041 (8)	0.0011 (8)
C4	0.0340 (8)	0.0373 (8)	0.0273 (8)	−0.0021 (6)	0.0038 (8)	−0.0019 (8)
C5	0.0320 (8)	0.0467 (10)	0.0327 (9)	−0.0036 (8)	−0.0052 (8)	−0.0020 (8)
C6	0.0352 (9)	0.0458 (10)	0.0349 (10)	0.0064 (8)	−0.0030 (8)	0.0038 (8)
C7	0.0701 (16)	0.0391 (12)	0.083 (2)	−0.0030 (11)	−0.0173 (15)	0.0059 (12)
C8	0.0468 (11)	0.0391 (11)	0.0599 (16)	−0.0038 (9)	−0.0042 (10)	−0.0035 (9)
C9	0.0571 (12)	0.0463 (11)	0.0654 (15)	−0.0088 (9)	0.0005 (14)	0.0007 (13)
C10	0.0658 (14)	0.0392 (11)	0.080 (2)	0.0088 (10)	0.0024 (14)	0.0063 (12)
C11	0.0502 (12)	0.0381 (10)	0.0655 (15)	0.0066 (9)	0.0077 (11)	0.0001 (10)
Cl1	0.1167 (6)	0.0368 (3)	0.0596 (4)	0.0072 (3)	−0.0038 (4)	−0.0031 (3)

O1—C4	1.378 (2)	C10—C11	1.514 (3)
O1—C7	1.423 (3)	C2—H2	0.9300
N1—C1	1.435 (2)	C3—H3	0.9300
N1—C8	1.463 (3)	C5—H5	0.9300
N1—C11	1.464 (3)	C6—H6	0.9300
N2—C9	1.474 (3)	C7—H7A	0.9600
N2—C10	1.480 (4)	C7—H7B	0.9600
N2—H2A	0.9000	C7—H7C	0.9600
N2—H2B	0.9000	C8—H8A	0.9700
C1—C2	1.393 (3)	C8—H8B	0.9700
C1—C6	1.396 (3)	C9—H9A	0.9700
C2—C3	1.397 (3)	C9—H9B	0.9700
C3—C4	1.379 (3)	C10—H10A	0.9700
C4—C5	1.399 (3)	C10—H10B	0.9700
C5—C6	1.373 (3)	C11—H11A	0.9700
C8—C9	1.520 (3)	C11—H11B	0.9700

Cl1···N2	3.134 (3)	H2···H8A	2.2600
Cl1···N2ⁱ	3.082 (2)	H2···H8B	2.3300
Cl1···H2Aⁱ	2.2000	H2A···Cl1^vi	2.2000
Cl1···H9Bⁱⁱ	3.1300	H2B···H11A	2.5200
Cl1···H2B	2.2400	H2B···Cl1	2.2400
Cl1···H7Aⁱⁱⁱ	2.9700	H2B···H8B	2.5000
O1···H2^iv	2.7700	H3···C5ⁱⁱⁱ	2.8500
O1···H8A^v	2.6500	H3···C7	2.5100
N1···N2	2.852 (3)	H3···H7B	2.2900
N2···N1	2.852 (3)	H3···H7C	2.2900
N2···Cl1	3.134 (3)	H3···C6ⁱⁱⁱ	2.9400
N2···Cl1^vi	3.082 (2)	H3···C5^vii	3.0900
N1···H7B^iv	2.8800	H5···C3^ix	2.8000
C2···C4ⁱⁱⁱ	3.549 (3)	H5···C3^v	2.9500
C3···C5^vii	3.435 (3)	H5···C4^ix	2.8800
C3···C5ⁱⁱⁱ	3.585 (3)	H6···C11	2.8700
C3···C4ⁱⁱⁱ	3.589 (3)	H6···H11B	2.3000
C4···C2^iv	3.549 (3)	H7A···Cl1^iv	2.9700
C4···C3^iv	3.589 (3)	H7B···C3	2.7400
C5···C3^v	3.435 (3)	H7B···C1ⁱⁱⁱ	2.8700
C5···C3^iv	3.585 (3)	H7B···H3	2.2900
C1···H7B^iv	2.8700	H7B···N1ⁱⁱⁱ	2.8800
C2···H8A	2.6700	H7B···H8Aⁱⁱⁱ	2.5800
C2···H8B	2.8500	H7C···H3	2.2900
C3···H5^viii	2.8000	H7C···C3	2.7300
C3···H5^vii	2.9500	H8A···C2	2.6700
C3···H7C	2.7300	H8A···H7B^iv	2.5800
C3···H7B	2.7400	H8A···O1^vii	2.6500
C4···H2^iv	3.0200	H8A···H2	2.2600
C4···H5^viii	2.8800	H8A···C7^vii	3.0500
C5···H3^v	3.0900	H8B···H2B	2.5000
C5···H3^iv	2.8500	H8B···H11A	2.4600
C6···H11B	2.6800	H8B···C2	2.8500
C6···H3^iv	2.9400	H8B···H2	2.3300
C7···H8A^v	3.0500	H9B···Cl1^x	3.1300
C7···H3	2.5100	H9B···H10A	2.5100
C8···H2	2.5200	H10A···H9B	2.5100
C11···H6	2.8700	H11A···H2B	2.5200
H2···C8	2.5200	H11A···H8B	2.4600
H2···C4ⁱⁱⁱ	3.0200	H11B···H6	2.3000
H2···O1ⁱⁱⁱ	2.7700	H11B···C6	2.6800

C4—O1—C7	116.79 (18)	C6—C5—H5	120.00
C1—N1—C8	115.97 (16)	C1—C6—H6	119.00
C1—N1—C11	114.48 (16)	C5—C6—H6	119.00
C8—N1—C11	110.85 (17)	O1—C7—H7A	109.00
C9—N2—C10	111.0 (2)	O1—C7—H7B	109.00
C9—N2—H2B	109.00	O1—C7—H7C	109.00
C10—N2—H2A	109.00	H7A—C7—H7B	109.00
C10—N2—H2B	109.00	H7A—C7—H7C	109.00
H2A—N2—H2B	108.00	H7B—C7—H7C	109.00
C9—N2—H2A	109.00	N1—C8—H8A	110.00
N1—C1—C2	122.78 (16)	N1—C8—H8B	110.00
N1—C1—C6	119.39 (17)	C9—C8—H8A	110.00
C2—C1—C6	117.76 (16)	C9—C8—H8B	110.00
C1—C2—C3	120.99 (17)	H8A—C8—H8B	108.00
C2—C3—C4	120.16 (18)	N2—C9—H9A	110.00
O1—C4—C5	115.99 (17)	N2—C9—H9B	110.00
O1—C4—C3	124.69 (18)	C8—C9—H9A	110.00
C3—C4—C5	119.31 (18)	C8—C9—H9B	110.00
C4—C5—C6	120.09 (18)	H9A—C9—H9B	108.00
C1—C6—C5	121.68 (18)	N2—C10—H10A	110.00
N1—C8—C9	109.88 (17)	N2—C10—H10B	110.00
N2—C9—C8	109.72 (19)	C11—C10—H10A	110.00
N2—C10—C11	110.0 (2)	C11—C10—H10B	110.00
N1—C11—C10	110.4 (2)	H10A—C10—H10B	108.00
C1—C2—H2	119.00	N1—C11—H11A	110.00
C3—C2—H2	120.00	N1—C11—H11B	110.00
C2—C3—H3	120.00	C10—C11—H11A	110.00
C4—C3—H3	120.00	C10—C11—H11B	110.00
C4—C5—H5	120.00	H11A—C11—H11B	108.00

C7—O1—C4—C3	−0.2 (3)	N1—C1—C2—C3	175.8 (2)
C7—O1—C4—C5	−178.8 (2)	C6—C1—C2—C3	−1.2 (3)
C8—N1—C1—C2	−10.2 (3)	N1—C1—C6—C5	−176.6 (2)
C8—N1—C1—C6	166.8 (2)	C2—C1—C6—C5	0.5 (3)
C11—N1—C1—C2	120.9 (2)	C1—C2—C3—C4	1.2 (3)
C11—N1—C1—C6	−62.2 (3)	C2—C3—C4—O1	−179.0 (2)
C1—N1—C8—C9	−168.1 (2)	C2—C3—C4—C5	−0.4 (3)
C11—N1—C8—C9	59.1 (3)	O1—C4—C5—C6	178.4 (2)
C1—N1—C11—C10	167.9 (2)	C3—C4—C5—C6	−0.3 (3)
C8—N1—C11—C10	−58.6 (3)	C4—C5—C6—C1	0.3 (3)
C10—N2—C9—C8	57.6 (3)	N1—C8—C9—N2	−58.2 (3)
C9—N2—C10—C11	−56.9 (3)	N2—C10—C11—N1	56.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^vi	0.90	2.20	3.082 (2)	168
N2—H2B···Cl1	0.90	2.24	3.134 (3)	177
C3—H3···CgAⁱⁱⁱ	0.93	2.88	3.573 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1ⁱ	0.90	2.20	3.082 (2)	168
N2—H2B⋯Cl1	0.90	2.24	3.134 (3)	177
C3—H3⋯CgAⁱⁱ	0.93	2.88	3.573 (2)	133

Symmetry codes: (i) ; (ii) . CgA is the centroid of the benzene ring.

2 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. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

2 in total

3 in total

1. Twelve 4-(4-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions: supra-molecular assembly in one, two and three dimensions.

Authors: Haruvegowda Kiran Kumar; Hemmige S Yathirajan; Sabine Foro; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2019-09-20

2. Six 1-aroyl-4-(4-meth-oxy-phen-yl)piperazines: similar mol-ecular structures but different patterns of supra-molecular assembly.

Authors: Haruvegowda Kiran Kumar; Hemmige S Yathirajan; Belakavadi K Sagar; Sabine Foro; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2019-07-26

3. Syntheses and crystal structures of 4-(4-meth-oxy-phen-yl)piperazin-1-ium 4-methyl-benzoate monohydrate and bis-[4-(4-meth-oxy-phen-yl)piperazin-1-ium] benzene-1,2-di-carboxyl-ate.

Authors: Holehundi J Shankara Prasad; Hemmige S Yathirajan; Sean R Parkin; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2022-08-26

3 in total