Diiso­propyl­ammonium 4-amino­benzene­sulfonate

The title mol­ecular salt, C₆H₁₆N⁺·C₆H₆NO₃S⁻, was synthesized from a neutralization reaction between sulfanilic acid and diiso­propyl­amine. The crystal structure consists of diiso­propyl­ammonium cations and 4-amino­benzene­sulfonate (sulfanilate) anions inter­acting through a series of N—H...O and C—H...O hydrogen bonds, leading to the formation of a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.136
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1N    ..  O3      ..       2.67 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.810 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           7 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Diisopropylammonium 4-aminobenzenesulfonate

Crystal data

C6H16N^+·C6H6NO3S^−	F(000) = 592
Mr = 274.38	Dx = 1.259 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2619 reflections
a = 8.1712 (4) Å	θ = 3.8–27.1°
b = 20.1515 (9) Å	µ = 0.23 mm^−1
c = 9.1360 (4) Å	T = 296 K
β = 105.806 (5)°	Fragment of big plate, colourless
V = 1447.47 (11) Å^3	0.42 × 0.26 × 0.18 mm
Z = 4

Data collection

Agilent Xcalibur Sapphire2 diffractometer	2963 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2340 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.3622 pixels mm^-1	θmax = 26.4°, θmin = 3.6°
ω scans	h = −9→10
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014)	k = −24→25
Tmin = 0.952, Tmax = 0.970	l = −11→11
6311 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.5536P] where P = (Fo^2 + 2Fc^2)/3
2963 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.34 e Å^−3
14 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8387 (2)	0.15317 (10)	0.7706 (2)	0.0370 (4)
C2	0.8828 (3)	0.20191 (11)	0.8832 (2)	0.0462 (5)
H2	0.8014	0.2179	0.9284	0.055*
C3	1.0462 (3)	0.22647 (11)	0.9277 (3)	0.0527 (6)
H3	1.0738	0.259	1.0027	0.063*
C4	1.1704 (3)	0.20355 (11)	0.8624 (3)	0.0469 (5)
C5	1.1258 (3)	0.15426 (11)	0.7514 (2)	0.0448 (5)
H5	1.2074	0.1377	0.7073	0.054*
C6	0.9619 (3)	0.12987 (10)	0.7063 (2)	0.0415 (5)
H6	0.9342	0.0973	0.6315	0.05*
N1	1.3337 (3)	0.22806 (13)	0.9042 (3)	0.0775 (8)
S1	0.62887 (6)	0.12319 (3)	0.71455 (6)	0.04264 (19)
O1	0.6264 (2)	0.06898 (9)	0.6105 (2)	0.0681 (5)
O2	0.5214 (2)	0.17641 (10)	0.6456 (3)	0.1034 (9)
O3	0.5882 (3)	0.09977 (13)	0.8485 (2)	0.0992 (8)
H1M	1.362 (4)	0.2562 (15)	0.975 (3)	0.119*
H1N	1.405 (3)	0.2074 (16)	0.871 (4)	0.119*
C7	0.2667 (3)	0.09559 (11)	0.2422 (3)	0.0511 (6)
H7	0.2799	0.1423	0.2176	0.061*
C8	0.1624 (4)	0.06106 (14)	0.1017 (3)	0.0700 (8)
H8A	0.2188	0.0645	0.0225	0.105*
H8B	0.0524	0.0816	0.0687	0.105*
H8C	0.1494	0.0151	0.1241	0.105*
C9	0.1832 (4)	0.09238 (17)	0.3702 (3)	0.0785 (9)
H9A	0.1652	0.0468	0.3924	0.118*
H9B	0.0759	0.1151	0.3407	0.118*
H9C	0.2554	0.1132	0.459	0.118*
C10	0.5643 (3)	0.08053 (12)	0.2043 (3)	0.0547 (6)
H10	0.5049	0.0785	0.0957	0.066*
C11	0.6339 (4)	0.14973 (14)	0.2419 (4)	0.0739 (8)
H11A	0.6931	0.1523	0.348	0.111*
H11B	0.5419	0.181	0.2191	0.111*
H11C	0.711	0.1599	0.1823	0.111*
C12	0.7029 (4)	0.02934 (15)	0.2389 (4)	0.0865 (10)
H12A	0.7822	0.0387	0.1809	0.13*
H12B	0.6543	−0.0138	0.2123	0.13*
H12C	0.761	0.0305	0.3454	0.13*
N2	0.4402 (2)	0.06439 (9)	0.2941 (2)	0.0454 (4)
H2M	0.489 (2)	0.0764 (11)	0.3896 (18)	0.054*
H2N	0.423 (2)	0.0211 (7)	0.292 (3)	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0406 (10)	0.0316 (10)	0.0346 (10)	−0.0003 (8)	0.0031 (8)	0.0024 (8)
C2	0.0475 (12)	0.0402 (11)	0.0500 (12)	0.0032 (10)	0.0118 (10)	−0.0093 (9)
C3	0.0564 (13)	0.0411 (12)	0.0551 (13)	−0.0046 (10)	0.0059 (11)	−0.0181 (10)
C4	0.0448 (12)	0.0404 (11)	0.0509 (12)	−0.0049 (10)	0.0051 (10)	−0.0006 (10)
C5	0.0447 (12)	0.0476 (12)	0.0432 (11)	−0.0021 (10)	0.0140 (9)	−0.0033 (9)
C6	0.0503 (12)	0.0410 (11)	0.0324 (10)	−0.0051 (9)	0.0100 (9)	−0.0061 (8)
N1	0.0490 (13)	0.0770 (18)	0.103 (2)	−0.0183 (12)	0.0153 (13)	−0.0326 (14)
S1	0.0397 (3)	0.0396 (3)	0.0442 (3)	−0.0028 (2)	0.0039 (2)	0.0011 (2)
O1	0.0552 (10)	0.0690 (12)	0.0768 (12)	−0.0175 (9)	0.0123 (9)	−0.0323 (10)
O2	0.0505 (11)	0.0571 (12)	0.173 (2)	0.0051 (9)	−0.0205 (13)	0.0298 (14)
O3	0.0780 (14)	0.162 (2)	0.0608 (12)	−0.0538 (15)	0.0235 (10)	0.0010 (14)
C7	0.0507 (13)	0.0405 (12)	0.0561 (13)	−0.0019 (10)	0.0041 (10)	−0.0012 (10)
C8	0.0728 (17)	0.0691 (17)	0.0521 (14)	−0.0021 (14)	−0.0102 (12)	0.0000 (13)
C9	0.0555 (16)	0.109 (2)	0.0722 (18)	−0.0051 (16)	0.0195 (13)	−0.0246 (18)
C10	0.0621 (14)	0.0582 (14)	0.0486 (13)	−0.0153 (12)	0.0231 (11)	−0.0065 (11)
C11	0.085 (2)	0.0542 (16)	0.090 (2)	−0.0174 (15)	0.0366 (17)	0.0077 (14)
C12	0.078 (2)	0.0658 (19)	0.134 (3)	−0.0093 (16)	0.060 (2)	−0.0197 (19)
N2	0.0478 (10)	0.0454 (10)	0.0415 (9)	−0.0075 (9)	0.0096 (8)	0.0018 (8)

Geometric parameters (Å, º)

C1—C6	1.379 (3)	C7—H7	0.98
C1—C2	1.396 (3)	C8—H8A	0.96
C1—S1	1.758 (2)	C8—H8B	0.96
C2—C3	1.377 (3)	C8—H8C	0.96
C2—H2	0.93	C9—H9A	0.96
C3—C4	1.389 (3)	C9—H9B	0.96
C3—H3	0.93	C9—H9C	0.96
C4—N1	1.376 (3)	C10—C12	1.501 (4)
C4—C5	1.395 (3)	C10—N2	1.503 (3)
C5—C6	1.380 (3)	C10—C11	1.510 (3)
C5—H5	0.93	C10—H10	0.98
C6—H6	0.93	C11—H11A	0.96
N1—H1M	0.841 (17)	C11—H11B	0.96
N1—H1N	0.839 (17)	C11—H11C	0.96
S1—O2	1.4201 (18)	C12—H12A	0.96
S1—O3	1.4325 (19)	C12—H12B	0.96
S1—O1	1.4446 (17)	C12—H12C	0.96
C7—C8	1.504 (3)	N2—H2M	0.888 (15)
C7—N2	1.505 (3)	N2—H2N	0.884 (14)
C7—C9	1.507 (4)
C6—C1—C2	118.81 (19)	H8A—C8—H8B	109.5
C6—C1—S1	121.74 (15)	C7—C8—H8C	109.5
C2—C1—S1	119.45 (16)	H8A—C8—H8C	109.5
C3—C2—C1	120.3 (2)	H8B—C8—H8C	109.5
C3—C2—H2	119.9	C7—C9—H9A	109.5
C1—C2—H2	119.9	C7—C9—H9B	109.5
C2—C3—C4	121.1 (2)	H9A—C9—H9B	109.5
C2—C3—H3	119.4	C7—C9—H9C	109.5
C4—C3—H3	119.4	H9A—C9—H9C	109.5
N1—C4—C3	121.9 (2)	H9B—C9—H9C	109.5
N1—C4—C5	119.9 (2)	C12—C10—N2	108.6 (2)
C3—C4—C5	118.1 (2)	C12—C10—C11	111.8 (2)
C6—C5—C4	120.7 (2)	N2—C10—C11	110.13 (19)
C6—C5—H5	119.6	C12—C10—H10	108.7
C4—C5—H5	119.6	N2—C10—H10	108.7
C1—C6—C5	120.85 (19)	C11—C10—H10	108.7
C1—C6—H6	119.6	C10—C11—H11A	109.5
C5—C6—H6	119.6	C10—C11—H11B	109.5
C4—N1—H1M	120 (2)	H11A—C11—H11B	109.5
C4—N1—H1N	116 (2)	C10—C11—H11C	109.5
H1M—N1—H1N	123 (3)	H11A—C11—H11C	109.5
O2—S1—O3	111.62 (17)	H11B—C11—H11C	109.5
O2—S1—O1	112.51 (14)	C10—C12—H12A	109.5
O3—S1—O1	110.36 (13)	C10—C12—H12B	109.5
O2—S1—C1	107.83 (10)	H12A—C12—H12B	109.5
O3—S1—C1	107.42 (10)	C10—C12—H12C	109.5
O1—S1—C1	106.82 (10)	H12A—C12—H12C	109.5
C8—C7—N2	110.0 (2)	H12B—C12—H12C	109.5
C8—C7—C9	111.8 (2)	C10—N2—C7	117.08 (18)
N2—C7—C9	108.9 (2)	C10—N2—H2M	107.0 (13)
C8—C7—H7	108.7	C7—N2—H2M	108.9 (13)
N2—C7—H7	108.7	C10—N2—H2N	109.0 (13)
C9—C7—H7	108.7	C7—N2—H2N	106.0 (13)
C7—C8—H8A	109.5	H2M—N2—H2N	109 (2)
C7—C8—H8B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2M···O1	0.89 (2)	2.03 (2)	2.878 (3)	159 (2)
N2—H2N···O1^i	0.88 (1)	2.11 (2)	2.922 (3)	152 (2)
N1—H1M···O2^ii	0.84 (2)	2.21 (2)	3.013 (3)	160 (3)
N1—H1N···O2^iii	0.84 (2)	2.57 (2)	3.316 (4)	149 (3)
N1—H1N···O3^iii	0.84 (2)	2.67 (2)	3.441 (4)	153 (3)
C10—H10···O3^iv	0.98	2.57	3.332 (3)	135
C12—H12B···O3^i	0.96	2.58	3.468 (4)	155

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