Di­propyl­ammonium 4-amino­benzene­sulfonate

Sarr, B.; Mbaye, A.; Touré, A.; Diop, C.A.K.; Sidibé, M.; Michaud, F.

doi:10.1107/S2414314620006598

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 5| May 2020| x200659

https://doi.org/10.1107/S2414314620006598

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Dipropylammonium 4-aminobenzenesulfonate

Bougar Sarr,^a ^* Abdou Mbaye,^b Assane Touré,^a Cheikh Abdoul Khadir Diop,^a Mamadou Sidibé ^a and François Michaud ^c

^aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Téchniques, Université Cheikh Anta Diop, Dakar, Senegal, ^bLaboratoire de Chimie et de Physique des Matériaux (LCPM) de l'Université Assane, Seck de Ziguinchor (UASZ), BP 523 Ziguinchor, Senegal, and ^cService Commun d'Analyse par Diffraction des Rayons X, Université de Bretagne Occidentale, 6, avenue Victor Le Gorgeu, CS 93837, F-29238 BREST cedex 3, France
^*Correspondence e-mail: bouks89@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 13 April 2020; accepted 16 May 2020; online 29 May 2020)

In the title molecular salt, NH₂(C₃H₇)₂⁺·[NH₂C₆H₄SO₃]⁻, the cation displays an extended conformation. In the crystal, anion-to-anion N—H⋯O and N—H⋯(O,O) hydrogen bonds generate (101) layers. Cation-to-anion N—H⋯O hydrogen bonds connect the layers into a three-dimensional network.

Keywords: crystal structure; hydrogen bonds; sulfanilate.

CCDC reference: 2004571

Structure description

Some sulfanilate-based compounds have high optical non-linearity and may be candidates for applications in optoelectronics and photonics in combination with organic cations such as guanidinium (Russell et al., 1994 ), triethylammonium (Li et al., 2007 ), diisopropylammonium (Sarr et al., 2016 ) and cyclohexylammonium (Kama et al., 2019 ). As part of our ongoing studies in this area (Sarr et al., 2016), we now describe the synthesis and crystal structure of the title molecular salt, which crystallizes in the non-centrosymmetric space group Pn.

The asymmetric unit, shown in Fig. 1, consists of one dipropylammonium NH₂(C₃H₇)₂⁺ cation and one 4-aminobenzenesulfonate [NH₂C₆H₄SO₃]⁻ anion. The cation adopts an extended structure with a minimum torsion angle of 174.7 (4)° for N2—C10—C11—C12. The involvement of the oxygen atoms of the sulfonate group in the anion as hydrogen-bond acceptors is manifested in a slight difference in the S—O bond lengths [S1—O1 = 1.446 (2), S1—O2 = 1.454 (2), S1—O3 = 1.449 (2) Å]: these data are consistent with those in sulfanilate anions previously reported (Sarr et al., 2016; Kama et al., 2019).

Figure 1
The asymmetric unit with displacement ellipsoids drawn at the 50% probability level. The N2—H2B⋯O2 hydrogen bond is shown as a dashed line.

In the extended structure, each sulfanilate anion interacts with four neighbours via simple N—H⋯O and bifurcated N—H⋯(O,O) hydrogen bonds (Table 1) to generate (101) layers (Fig. 2). The dipropylammonium cations play the role of bridges between the infinite anion layers via cation-to-anion N—H⋯O hydrogen bonds (Fig. 3) to generate a three-dimensional network. Each sulfanilate anion is thus surrounded by four anions and two cations.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.90 (2)	2.39 (3)	3.196 (4)	149 (4)
N1—H1A⋯O3ⁱ	0.90 (2)	2.49 (3)	3.313 (4)	153 (4)
N1—H1B⋯O1ⁱⁱ	0.88 (2)	2.08 (2)	2.940 (4)	165 (4)
N2—H2A⋯O3ⁱⁱⁱ	0.91 (2)	1.91 (2)	2.801 (3)	164 (3)
N2—H2B⋯O2	0.90 (2)	1.95 (3)	2.786 (3)	154 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
A perspective view of an infinite layer, viewed along the a and b axes.

Figure 3
The packing viewed along [010].

Synthesis and crystallization

A 1:2 mixture of sulfanilic acid (1.00 g, 5.80 mmol) and dipropylammine (1.16 g, 11.50 mmol) was dissolved in water and the colourless solution obtained was stirred for an hour. After a few days of evaporation in an oven at 333 K, some yellowish crystals were collected from the solution and then dried in air. The IR spectrum and peak assignments are given in the supporting information.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₆H₆NO₃S⁻
M_r	274.38
Crystal system, space group	Monoclinic, Pn
Temperature (K)	293
a, b, c (Å)	10.2564 (7), 6.5369 (5), 10.9683 (9)
β (°)	95.067 (7)
V (Å³)	732.50 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.22
Crystal size (mm)	0.38 × 0.28 × 0.19

Data collection
Diffractometer	Agilent Xcalibur, Sapphire2
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	21351, 4018, 3387
R_int	0.149
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.17
No. of reflections	4018
No. of parameters	181
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.28
Absolute structure	Flack (1983 )
Absolute structure parameter	0.09 (6)
Computer programs: SHELXT (Sheldrick, 2015 ), SHELXL97 (Sheldrick, 2008 ), OLEX2 (Dolomanov et al., 2009 ) ORTEP-3 for Windows (Farrugia, 2012 ) Mercury (Macrae et al., 2020 ), OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 2012), PLATON (Spek, 2020 ), enCIFer (Allen et al., 2004 ).

Structural data

CCDC reference: 2004571

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314620006598/hb4347sup1.cif

IR spectrum. DOI: https://doi.org/10.1107/S2414314620006598/hb4347sup3.docx

Supporting information file. DOI: https://doi.org/10.1107/S2414314620006598/hb4347Isup3.cml

checkCIF report

Computing details top

Data collection: ?; cell refinement: ?; data reduction: ?; program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) ORTEP-3 for Windows (Farrugia, 2012) Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 2012), PLATON (Spek, 2020), enCIFer (Allen et al., 2004).

Dipropylazanium 4-aminobenzenesulfonate top

Crystal data top

C₆H₁₆N⁺·C₆H₆NO₃S⁻	F(000) = 296
M_r = 274.38	D_x = 1.244 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 10.2564 (7) Å	Cell parameters from 38522 reflections
b = 6.5369 (5) Å	θ = 3.5–37.4°
c = 10.9683 (9) Å	µ = 0.22 mm⁻¹
β = 95.067 (7)°	T = 293 K
V = 732.50 (10) Å³	Block, clear light colourless
Z = 2	0.38 × 0.28 × 0.19 mm

Data collection top

Agilent Xcalibur, Sapphire2 diffractometer	3387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.149
ω scans	θ_max = 29.8°, θ_min = 6.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→14
T_min = 0.669, T_max = 0.746	k = −9→9
21351 measured reflections	l = −15→15
4018 independent reflections

Refinement top

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.P)² + 0.0621P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.003
4018 reflections	Δρ_max = 0.21 e Å⁻³
181 parameters	Δρ_min = −0.28 e Å⁻³
13 restraints	Absolute structure: Flack (1983)
34 constraints	Absolute structure parameter: 0.09 (6)
Primary atom site location: structure-invariant direct methods

Special details top

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 > 2σ(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.

The C-bound H atoms were geometrically placed and refined as riding atoms. The N-bound H atoms were located in difference maps and their positions were freely refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2799 (2)	0.3112 (4)	0.2052 (2)	0.0367 (5)
C2	0.2417 (3)	0.1097 (4)	0.2172 (3)	0.0445 (6)
H2	0.265741	0.011733	0.161908	0.053*
C3	0.1673 (3)	0.0538 (4)	0.3118 (3)	0.0478 (6)
H3	0.142230	−0.082099	0.319082	0.057*
C4	0.1296 (3)	0.1968 (4)	0.3958 (2)	0.0422 (6)
C5	0.1670 (3)	0.4010 (4)	0.3810 (3)	0.0437 (6)
H5	0.141106	0.500353	0.434520	0.052*
C6	0.2419 (3)	0.4561 (4)	0.2879 (2)	0.0413 (6)
H6	0.267171	0.591786	0.280253	0.050*
N1	0.0600 (3)	0.1413 (5)	0.4919 (3)	0.0648 (8)
O1	0.3872 (3)	0.2145 (4)	0.0083 (2)	0.0685 (7)
O2	0.4990 (2)	0.4606 (4)	0.1461 (2)	0.0629 (6)
O3	0.3054 (2)	0.5583 (3)	0.02517 (18)	0.0554 (6)
H1A	0.012 (4)	0.243 (5)	0.520 (4)	0.088 (14)*
H1B	0.018 (3)	0.024 (5)	0.488 (4)	0.072 (12)*
C7	0.9403 (4)	0.6507 (8)	0.1124 (4)	0.0829 (12)
H7A	0.909563	0.612015	0.030421	0.124*
H7B	1.021641	0.582605	0.135713	0.124*
H7C	0.953392	0.796103	0.116045	0.124*
C8	0.8400 (3)	0.5899 (5)	0.1991 (3)	0.0614 (9)
H8A	0.867832	0.640996	0.280284	0.074*
H8B	0.757055	0.654361	0.172644	0.074*
C9	0.8201 (3)	0.3642 (5)	0.2060 (3)	0.0530 (7)
H9A	0.901763	0.299306	0.235920	0.064*
H9B	0.794755	0.311445	0.124654	0.064*
C10	0.6895 (3)	0.0913 (5)	0.3018 (3)	0.0516 (8)
H10A	0.768416	0.021660	0.334665	0.062*
H10B	0.663027	0.033385	0.221981	0.062*
C11	0.5834 (4)	0.0585 (5)	0.3850 (3)	0.0591 (8)
H11A	0.507946	0.140033	0.355995	0.071*
H11B	0.613660	0.106484	0.466270	0.071*
C12	0.5419 (4)	−0.1628 (7)	0.3930 (5)	0.0802 (12)
H12A	0.512348	−0.211830	0.312830	0.120*
H12B	0.472165	−0.173525	0.445549	0.120*
H12C	0.614985	−0.243529	0.425863	0.120*
N2	0.7169 (2)	0.3125 (4)	0.2888 (2)	0.0435 (5)
S1	0.37479 (6)	0.38949 (10)	0.08711 (6)	0.04080 (17)
H2A	0.734 (3)	0.372 (4)	0.364 (2)	0.064 (10)*
H2B	0.644 (2)	0.382 (4)	0.264 (3)	0.069 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0348 (12)	0.0419 (13)	0.0332 (11)	0.0043 (10)	0.0018 (9)	0.0014 (9)
C2	0.0517 (17)	0.0382 (13)	0.0438 (14)	0.0021 (11)	0.0060 (12)	−0.0044 (11)
C3	0.0528 (16)	0.0376 (13)	0.0533 (16)	−0.0064 (12)	0.0073 (13)	−0.0001 (12)
C4	0.0381 (13)	0.0457 (14)	0.0427 (13)	−0.0032 (11)	0.0033 (11)	0.0007 (11)
C5	0.0461 (15)	0.0431 (14)	0.0427 (14)	−0.0006 (11)	0.0087 (12)	−0.0080 (10)
C6	0.0455 (14)	0.0349 (12)	0.0437 (14)	−0.0006 (10)	0.0049 (12)	−0.0033 (10)
N1	0.072 (2)	0.0622 (18)	0.0641 (18)	−0.0099 (15)	0.0292 (16)	0.0007 (14)
O1	0.0877 (17)	0.0627 (14)	0.0594 (13)	0.0110 (13)	0.0303 (12)	−0.0067 (12)
O2	0.0394 (11)	0.0936 (17)	0.0546 (12)	−0.0071 (11)	−0.0020 (10)	0.0245 (12)
O3	0.0606 (13)	0.0637 (13)	0.0416 (11)	0.0157 (11)	0.0023 (10)	0.0158 (10)
C7	0.066 (2)	0.116 (3)	0.065 (2)	−0.023 (2)	0.0032 (19)	0.010 (2)
C8	0.061 (2)	0.073 (2)	0.0502 (17)	−0.0077 (17)	0.0041 (16)	0.0003 (15)
C9	0.0443 (16)	0.069 (2)	0.0448 (15)	0.0084 (14)	0.0000 (13)	−0.0059 (13)
C10	0.058 (2)	0.0487 (17)	0.0464 (16)	0.0045 (13)	−0.0052 (14)	−0.0062 (12)
C11	0.062 (2)	0.0575 (19)	0.0567 (18)	0.0025 (16)	−0.0017 (16)	0.0008 (15)
C12	0.075 (3)	0.068 (2)	0.096 (3)	−0.010 (2)	0.000 (2)	0.012 (2)
N2	0.0454 (12)	0.0454 (13)	0.0383 (11)	0.0061 (11)	−0.0038 (9)	−0.0062 (10)
S1	0.0402 (3)	0.0483 (3)	0.0339 (3)	0.0074 (3)	0.0033 (2)	0.0044 (3)

Geometric parameters (Å, º) top

C1—C2	1.384 (3)	C7—C8	1.515 (5)
C1—C6	1.391 (3)	C8—H8A	0.9700
C1—S1	1.763 (3)	C8—H8B	0.9700
C2—H2	0.9300	C8—C9	1.492 (5)
C2—C3	1.390 (4)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C3—C4	1.391 (4)	C9—N2	1.493 (4)
C4—C5	1.402 (4)	C10—H10A	0.9700
C4—N1	1.373 (4)	C10—H10B	0.9700
C5—H5	0.9300	C10—C11	1.496 (5)
C5—C6	1.378 (4)	C10—N2	1.483 (4)
C6—H6	0.9300	C11—H11A	0.9700
N1—H1A	0.90 (2)	C11—H11B	0.9700
N1—H1B	0.88 (2)	C11—C12	1.513 (5)
O1—S1	1.446 (2)	C12—H12A	0.9600
O2—S1	1.454 (2)	C12—H12B	0.9600
O3—S1	1.449 (2)	C12—H12C	0.9600
C7—H7A	0.9600	N2—H2A	0.91 (2)
C7—H7B	0.9600	N2—H2B	0.90 (2)
C7—H7C	0.9600

C2—C1—C6	119.2 (2)	C8—C9—N2	111.2 (2)
C2—C1—S1	121.7 (2)	H9A—C9—H9B	108.0
C6—C1—S1	119.1 (2)	N2—C9—H9A	109.4
C1—C2—H2	120.0	N2—C9—H9B	109.4
C1—C2—C3	120.0 (3)	H10A—C10—H10B	108.1
C3—C2—H2	120.0	C11—C10—H10A	109.5
C2—C3—H3	119.3	C11—C10—H10B	109.5
C2—C3—C4	121.4 (3)	N2—C10—H10A	109.5
C4—C3—H3	119.3	N2—C10—H10B	109.5
C3—C4—C5	117.9 (2)	N2—C10—C11	110.7 (3)
N1—C4—C3	121.6 (3)	C10—C11—H11A	108.9
N1—C4—C5	120.4 (3)	C10—C11—H11B	108.9
C4—C5—H5	119.6	C10—C11—C12	113.3 (3)
C6—C5—C4	120.7 (2)	H11A—C11—H11B	107.7
C6—C5—H5	119.6	C12—C11—H11A	108.9
C1—C6—H6	119.6	C12—C11—H11B	108.9
C5—C6—C1	120.8 (2)	C11—C12—H12A	109.5
C5—C6—H6	119.6	C11—C12—H12B	109.5
C4—N1—H1A	114 (3)	C11—C12—H12C	109.5
C4—N1—H1B	118 (3)	H12A—C12—H12B	109.5
H1A—N1—H1B	113 (4)	H12A—C12—H12C	109.5
H7A—C7—H7B	109.5	H12B—C12—H12C	109.5
H7A—C7—H7C	109.5	C9—N2—H2A	112 (2)
H7B—C7—H7C	109.5	C9—N2—H2B	109 (2)
C8—C7—H7A	109.5	C10—N2—C9	115.5 (2)
C8—C7—H7B	109.5	C10—N2—H2A	110.4 (19)
C8—C7—H7C	109.5	C10—N2—H2B	111 (2)
C7—C8—H8A	108.9	H2A—N2—H2B	98 (3)
C7—C8—H8B	108.9	O1—S1—C1	107.05 (13)
H8A—C8—H8B	107.7	O1—S1—O2	113.52 (17)
C9—C8—C7	113.2 (3)	O1—S1—O3	112.81 (14)
C9—C8—H8A	108.9	O2—S1—C1	106.52 (12)
C9—C8—H8B	108.9	O3—S1—C1	106.58 (12)
C8—C9—H9A	109.4	O3—S1—O2	109.88 (15)
C8—C9—H9B	109.4

C1—C2—C3—C4	0.1 (4)	C6—C1—S1—O1	−173.8 (2)
C2—C1—C6—C5	0.1 (4)	C6—C1—S1—O2	64.5 (2)
C2—C1—S1—O1	5.8 (3)	C6—C1—S1—O3	−52.8 (2)
C2—C1—S1—O2	−116.0 (2)	N1—C4—C5—C6	177.1 (3)
C2—C1—S1—O3	126.7 (2)	C7—C8—C9—N2	−177.9 (3)
C2—C3—C4—C5	1.1 (4)	C8—C9—N2—C10	179.9 (3)
C2—C3—C4—N1	−177.7 (3)	C11—C10—N2—C9	−179.1 (3)
C3—C4—C5—C6	−1.7 (4)	N2—C10—C11—C12	174.7 (3)
C4—C5—C6—C1	1.2 (4)	S1—C1—C2—C3	179.8 (2)
C6—C1—C2—C3	−0.7 (4)	S1—C1—C6—C5	179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.90 (2)	2.39 (3)	3.196 (4)	149 (4)
N1—H1A···O3ⁱ	0.90 (2)	2.49 (3)	3.313 (4)	153 (4)
N1—H1B···O1ⁱⁱ	0.88 (2)	2.08 (2)	2.940 (4)	165 (4)
N2—H2A···O3ⁱⁱⁱ	0.91 (2)	1.91 (2)	2.801 (3)	164 (3)
N2—H2B···O2	0.90 (2)	1.95 (3)	2.786 (3)	154 (3)

Symmetry codes: (i) x−1/2, −y+1, z+1/2; (ii) x−1/2, −y, z+1/2; (iii) x+1/2, −y+1, z+1/2.

Acknowledgements

The authors thank the Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Téchniques, Université Cheikh Anta Diop de Dakar, Sénégal, the Laboratoire de Chimie et de Physique des Matériaux (LCPM) de l'Université Assane Seck de Ziguinchor (UASZ), Sénégal and the Service Commun d'Analyse par Diffraction des Rayons X, Université de Bretagne Occidentale, France for financial support.

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