A dianionic 5-sulfonatosalicylate species in the proton-transfer compound bis­(benzyl­aminium) 3-carboxyl­ato-4-hydroxy­benzene­sulfonate

The crystal structure of anhydrous bis­(benzyl­aminium) 5-sulfonatosalicylate, 2C₇H₁₀N⁺·C₇H₄O₆S^2-, from the reaction of benzyl­amine with 5-sulfosalicylic acid, shows the presence of a dianionic 5-sulfonatosalicylate species, uncommon among proton-transfer compounds of this acid with organic Lewis bases. Hydrogen-bonding inter­actions between both aminium N⁺-H groups of the two cations and both the sulfonate and carboxyl­ate O-atom acceptors of the anions give a layered two-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.172
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C7 H10 N

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   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

bis(benzylaminium) 3-carboxylato-4-hydroxybenzenesulfonate

Crystal data

2C7H10N^+·C7H4O6S^2^−	F(000) = 1824
Mr = 432.48	Dx = 1.383 Mg m^−3
Monoclinic, C2/c	Melting point = 303.6–305.6 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71069 Å
a = 24.686 (5) Å	Cell parameters from 25 reflections
b = 5.144 (2) Å	θ = 10.1–16.3°
c = 32.705 (6) Å	µ = 0.20 mm^−1
β = 90.111 (14)°	T = 297 K
V = 4153 (2) Å^3	Prism, colourless
Z = 8	0.35 × 0.27 × 0.18 mm

Data collection

Rigaku AFC-7R diffractometer	2396 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 3.0°
ω–2θ scans	h = −32→14
Absorption correction: ψ scan (TEXSAN; Molecular Structure Corporation, 1999)	k = 0→6
Tmin = 0.934, Tmax = 0.965	l = −42→42
5249 measured reflections	3 standard reflections every 150 min
4768 independent reflections	intensity decay: 2.3%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
4768 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
S5	0.48779 (3)	0.47455 (14)	0.18196 (2)	0.0316 (2)
O2	0.34934 (10)	0.2368 (6)	0.03971 (8)	0.0537 (9)
O51	0.53661 (10)	0.3257 (5)	0.17995 (7)	0.0514 (9)
O52	0.45402 (10)	0.4073 (6)	0.21680 (7)	0.0593 (9)
O53	0.49637 (14)	0.7531 (5)	0.18146 (8)	0.0711 (10)
O71	0.49407 (10)	−0.1557 (5)	0.05223 (7)	0.0459 (8)
O72	0.41191 (9)	−0.1450 (5)	0.02373 (7)	0.0467 (8)
C1	0.42975 (12)	0.1405 (6)	0.07870 (8)	0.0292 (9)
C2	0.38301 (12)	0.2871 (6)	0.07147 (9)	0.0336 (9)
C3	0.37014 (12)	0.4948 (6)	0.09728 (9)	0.0368 (10)
C4	0.40244 (13)	0.5528 (6)	0.13011 (9)	0.0340 (10)
C5	0.44823 (12)	0.4024 (6)	0.13831 (8)	0.0286 (8)
C6	0.46157 (12)	0.1976 (6)	0.11296 (9)	0.0288 (9)
C7	0.44645 (13)	−0.0709 (6)	0.05008 (9)	0.0341 (10)
N8A	0.54934 (12)	0.3749 (6)	0.04432 (10)	0.0379 (9)
C1A	0.63765 (13)	0.2581 (7)	0.07593 (10)	0.0415 (11)
C2A	0.67731 (15)	0.2316 (8)	0.04653 (12)	0.0527 (12)
C3A	0.71649 (15)	0.0390 (9)	0.05022 (14)	0.0633 (16)
C4A	0.71643 (16)	−0.1228 (8)	0.08334 (14)	0.0584 (14)
C5A	0.67727 (17)	−0.0961 (8)	0.11325 (13)	0.0574 (12)
C6A	0.63804 (15)	0.0953 (8)	0.10929 (11)	0.0497 (12)
C7A	0.59472 (14)	0.4634 (7)	0.07083 (11)	0.0487 (12)
N8B	0.43263 (12)	−0.0641 (8)	0.25756 (10)	0.0461 (10)
C1B	0.33757 (13)	−0.1033 (7)	0.23333 (10)	0.0391 (10)
C2B	0.30029 (15)	−0.3034 (8)	0.23159 (12)	0.0503 (12)
C3B	0.26542 (15)	−0.3248 (8)	0.19848 (13)	0.0543 (14)
C4B	0.26757 (14)	−0.1504 (7)	0.16689 (12)	0.0497 (12)
C5B	0.30399 (15)	0.0493 (7)	0.16847 (12)	0.0514 (12)
C6B	0.33909 (14)	0.0738 (7)	0.20144 (11)	0.0460 (12)
C7B	0.37482 (15)	−0.0774 (8)	0.26945 (11)	0.0526 (14)
H2	0.3649 (17)	0.092 (9)	0.0274 (13)	0.073 (14)*
H3	0.33870	0.59640	0.09200	0.0440*
H4	0.39370	0.69560	0.14730	0.0410*
H6	0.49260	0.09470	0.11890	0.0350*
H2A	0.67780	0.34550	0.02360	0.0630*
H3A	0.74340	0.02010	0.02970	0.0760*
H4A	0.74330	−0.25410	0.08580	0.0700*
H5A	0.67730	−0.20840	0.13630	0.0690*
H6A	0.61110	0.11430	0.12990	0.0600*
H71A	0.61070	0.61320	0.05890	0.0580*
H72A	0.58070	0.50670	0.09700	0.0580*
H81A	0.5252 (15)	0.518 (9)	0.0438 (12)	0.063 (12)*
H82A	0.5633 (14)	0.333 (7)	0.0192 (12)	0.042 (10)*
H83A	0.5343 (16)	0.225 (9)	0.0544 (12)	0.061 (12)*
H2B	0.29860	−0.42700	0.25310	0.0610*
H3B	0.23960	−0.46190	0.19780	0.0650*
H4B	0.24400	−0.16840	0.14400	0.0600*
H5B	0.30530	0.17240	0.14680	0.0620*
H6B	0.36440	0.21310	0.20210	0.0550*
H71B	0.36980	−0.22360	0.28680	0.0630*
H72B	0.36580	0.07680	0.28390	0.0630*
H81B	0.4409 (16)	−0.194 (8)	0.2403 (12)	0.064 (12)*
H82B	0.4557 (17)	−0.080 (8)	0.2790 (14)	0.072 (13)*
H83B	0.440 (2)	0.093 (12)	0.2424 (18)	0.073 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S5	0.0395 (4)	0.0291 (4)	0.0262 (4)	−0.0013 (3)	−0.0091 (3)	−0.0020 (3)
O2	0.0439 (15)	0.0694 (19)	0.0478 (15)	0.0098 (13)	−0.0225 (12)	−0.0199 (14)
O51	0.0444 (14)	0.0665 (17)	0.0433 (14)	0.0152 (13)	−0.0153 (11)	−0.0131 (12)
O52	0.0532 (16)	0.098 (2)	0.0266 (12)	−0.0140 (15)	−0.0028 (11)	−0.0017 (13)
O53	0.117 (2)	0.0290 (14)	0.0670 (17)	−0.0093 (14)	−0.0548 (17)	−0.0027 (13)
O71	0.0440 (14)	0.0457 (14)	0.0479 (14)	0.0135 (11)	−0.0035 (11)	−0.0155 (11)
O72	0.0492 (14)	0.0550 (15)	0.0360 (13)	−0.0008 (12)	−0.0083 (11)	−0.0190 (11)
C1	0.0329 (16)	0.0309 (16)	0.0239 (14)	−0.0027 (13)	0.0009 (12)	−0.0011 (12)
C2	0.0304 (16)	0.0393 (17)	0.0312 (15)	0.0011 (14)	−0.0070 (12)	−0.0017 (13)
C3	0.0326 (16)	0.0415 (18)	0.0364 (16)	0.0086 (15)	−0.0072 (13)	0.0000 (15)
C4	0.0403 (18)	0.0292 (16)	0.0324 (16)	0.0044 (13)	−0.0025 (13)	−0.0053 (12)
C5	0.0319 (15)	0.0293 (15)	0.0245 (14)	−0.0026 (13)	−0.0061 (12)	0.0000 (11)
C6	0.0309 (16)	0.0275 (14)	0.0279 (15)	0.0036 (12)	−0.0051 (12)	−0.0002 (12)
C7	0.0383 (18)	0.0347 (17)	0.0292 (16)	−0.0025 (14)	0.0002 (13)	−0.0041 (12)
N8A	0.0346 (16)	0.0432 (17)	0.0360 (16)	0.0045 (14)	−0.0030 (12)	−0.0098 (14)
C1A	0.0303 (18)	0.047 (2)	0.047 (2)	0.0007 (15)	−0.0108 (15)	−0.0144 (16)
C2A	0.043 (2)	0.059 (2)	0.056 (2)	0.0002 (19)	−0.0029 (17)	0.0010 (19)
C3A	0.035 (2)	0.085 (3)	0.070 (3)	0.009 (2)	0.0011 (18)	−0.010 (3)
C4A	0.042 (2)	0.056 (2)	0.077 (3)	0.0084 (19)	−0.020 (2)	−0.011 (2)
C5A	0.057 (2)	0.055 (2)	0.060 (2)	−0.003 (2)	−0.027 (2)	0.0002 (19)
C6A	0.046 (2)	0.061 (2)	0.042 (2)	−0.0039 (18)	−0.0108 (16)	−0.0070 (17)
C7A	0.044 (2)	0.050 (2)	0.052 (2)	0.0035 (17)	−0.0150 (16)	−0.0187 (17)
N8B	0.0400 (17)	0.066 (2)	0.0321 (15)	0.0147 (16)	−0.0097 (13)	−0.0096 (16)
C1B	0.0354 (18)	0.0418 (18)	0.0402 (18)	0.0021 (15)	0.0040 (14)	−0.0065 (15)
C2B	0.048 (2)	0.048 (2)	0.055 (2)	0.0003 (18)	0.0060 (18)	0.0040 (18)
C3B	0.044 (2)	0.050 (2)	0.069 (3)	−0.0131 (18)	−0.0002 (19)	−0.0061 (19)
C4B	0.039 (2)	0.051 (2)	0.059 (2)	0.0002 (17)	−0.0108 (17)	−0.0077 (18)
C5B	0.051 (2)	0.047 (2)	0.056 (2)	−0.0039 (18)	−0.0094 (17)	0.0060 (17)
C6B	0.043 (2)	0.044 (2)	0.051 (2)	−0.0088 (16)	−0.0072 (16)	0.0009 (16)
C7B	0.045 (2)	0.077 (3)	0.0357 (19)	−0.0014 (19)	−0.0012 (15)	−0.0058 (18)

Geometric parameters (Å, º)

S5—O51	1.430 (3)	C1A—C6A	1.375 (5)
S5—O52	1.455 (3)	C1A—C7A	1.505 (5)
S5—O53	1.449 (3)	C2A—C3A	1.390 (6)
S5—C5	1.768 (3)	C3A—C4A	1.366 (6)
O2—C2	1.354 (4)	C4A—C5A	1.384 (6)
O71—C7	1.256 (4)	C5A—C6A	1.387 (6)
O72—C7	1.270 (4)	C2A—H2A	0.9500
O2—H2	0.93 (4)	C3A—H3A	0.9500
N8A—C7A	1.487 (5)	C4A—H4A	0.9500
N8A—H82A	0.92 (4)	C5A—H5A	0.9500
N8A—H83A	0.92 (4)	C6A—H6A	0.9500
N8A—H81A	0.95 (4)	C7A—H71A	0.9500
N8B—C7B	1.481 (5)	C7A—H72A	0.9500
N8B—H83B	0.97 (6)	C1B—C7B	1.502 (5)
N8B—H82B	0.91 (5)	C1B—C2B	1.382 (5)
N8B—H81B	0.90 (4)	C1B—C6B	1.385 (5)
C1—C7	1.493 (4)	C2B—C3B	1.386 (6)
C1—C2	1.398 (4)	C3B—C4B	1.369 (6)
C1—C6	1.398 (4)	C4B—C5B	1.366 (5)
C2—C3	1.399 (4)	C5B—C6B	1.388 (5)
C3—C4	1.369 (4)	C2B—H2B	0.9500
C4—C5	1.395 (4)	C3B—H3B	0.9500
C5—C6	1.381 (4)	C4B—H4B	0.9500
C3—H3	0.9500	C5B—H5B	0.9500
C4—H4	0.9500	C6B—H6B	0.9500
C6—H6	0.9500	C7B—H71B	0.9500
C1A—C2A	1.380 (5)	C7B—H72B	0.9500
O51—S5—O52	113.15 (15)	C2A—C3A—C4A	120.1 (4)
O51—S5—O53	113.96 (18)	C3A—C4A—C5A	120.1 (4)
O51—S5—C5	108.36 (14)	C4A—C5A—C6A	119.6 (4)
O52—S5—O53	109.15 (17)	C1A—C6A—C5A	120.7 (3)
O52—S5—C5	105.43 (14)	N8A—C7A—C1A	112.3 (3)
O53—S5—C5	106.21 (16)	C3A—C2A—H2A	120.00
C2—O2—H2	103 (3)	C1A—C2A—H2A	120.00
C7A—N8A—H82A	108 (2)	C2A—C3A—H3A	120.00
C7A—N8A—H83A	111 (2)	C4A—C3A—H3A	120.00
H81A—N8A—H82A	114 (3)	C3A—C4A—H4A	120.00
H81A—N8A—H83A	114 (4)	C5A—C4A—H4A	120.00
H82A—N8A—H83A	106 (3)	C6A—C5A—H5A	120.00
C7A—N8A—H81A	104 (2)	C4A—C5A—H5A	120.00
C7B—N8B—H83B	111 (3)	C1A—C6A—H6A	120.00
H81B—N8B—H82B	106 (4)	C5A—C6A—H6A	120.00
H82B—N8B—H83B	111 (4)	H71A—C7A—H72A	109.00
C7B—N8B—H81B	111 (3)	N8A—C7A—H72A	109.00
H81B—N8B—H83B	105 (4)	N8A—C7A—H71A	109.00
C7B—N8B—H82B	113 (3)	C1A—C7A—H71A	109.00
C2—C1—C7	121.0 (3)	C1A—C7A—H72A	109.00
C6—C1—C7	120.0 (3)	C2B—C1B—C7B	120.4 (3)
C2—C1—C6	119.0 (3)	C2B—C1B—C6B	118.5 (3)
O2—C2—C3	118.0 (3)	C6B—C1B—C7B	121.1 (3)
C1—C2—C3	119.9 (3)	C1B—C2B—C3B	120.3 (4)
O2—C2—C1	122.1 (3)	C2B—C3B—C4B	120.8 (4)
C2—C3—C4	120.5 (3)	C3B—C4B—C5B	119.4 (4)
C3—C4—C5	120.0 (3)	C4B—C5B—C6B	120.5 (4)
C4—C5—C6	120.1 (3)	C1B—C6B—C5B	120.5 (3)
S5—C5—C4	119.0 (2)	N8B—C7B—C1B	112.7 (3)
S5—C5—C6	120.9 (2)	C1B—C2B—H2B	120.00
C1—C6—C5	120.5 (3)	C3B—C2B—H2B	120.00
O71—C7—C1	118.5 (3)	C2B—C3B—H3B	119.00
O71—C7—O72	124.1 (3)	C4B—C3B—H3B	120.00
O72—C7—C1	117.3 (3)	C3B—C4B—H4B	120.00
C2—C3—H3	120.00	C5B—C4B—H4B	120.00
C4—C3—H3	120.00	C4B—C5B—H5B	120.00
C5—C4—H4	120.00	C6B—C5B—H5B	120.00
C3—C4—H4	120.00	C1B—C6B—H6B	120.00
C1—C6—H6	120.00	C5B—C6B—H6B	120.00
C5—C6—H6	120.00	N8B—C7B—H71B	109.00
C6A—C1A—C7A	121.3 (3)	N8B—C7B—H72B	109.00
C2A—C1A—C6A	119.3 (3)	C1B—C7B—H71B	109.00
C2A—C1A—C7A	119.5 (3)	C1B—C7B—H72B	109.00
C1A—C2A—C3A	120.3 (4)	H71B—C7B—H72B	109.00
O51—S5—C5—C4	−170.3 (2)	C4—C5—C6—C1	0.6 (4)
O51—S5—C5—C6	10.9 (3)	C6A—C1A—C2A—C3A	1.3 (6)
O52—S5—C5—C4	68.3 (3)	C7A—C1A—C2A—C3A	−178.4 (4)
O52—S5—C5—C6	−110.5 (3)	C2A—C1A—C6A—C5A	−0.9 (6)
O53—S5—C5—C4	−47.5 (3)	C2A—C1A—C7A—N8A	83.7 (4)
O53—S5—C5—C6	133.7 (3)	C7A—C1A—C6A—C5A	178.8 (3)
C6—C1—C2—C3	2.9 (4)	C6A—C1A—C7A—N8A	−96.1 (4)
C6—C1—C2—O2	−177.7 (3)	C1A—C2A—C3A—C4A	−1.0 (6)
C2—C1—C7—O72	−13.1 (4)	C2A—C3A—C4A—C5A	0.2 (6)
C6—C1—C7—O71	−15.1 (4)	C3A—C4A—C5A—C6A	0.2 (6)
C2—C1—C7—O71	163.8 (3)	C4A—C5A—C6A—C1A	0.1 (6)
C6—C1—C7—O72	168.1 (3)	C6B—C1B—C2B—C3B	0.1 (5)
C7—C1—C2—C3	−175.9 (3)	C7B—C1B—C2B—C3B	179.1 (3)
C2—C1—C6—C5	−2.6 (4)	C2B—C1B—C7B—N8B	126.2 (4)
C7—C1—C6—C5	176.2 (3)	C6B—C1B—C7B—N8B	−54.8 (5)
C7—C1—C2—O2	3.5 (5)	C2B—C1B—C6B—C5B	−0.2 (5)
O2—C2—C3—C4	179.3 (3)	C7B—C1B—C6B—C5B	−179.2 (3)
C1—C2—C3—C4	−1.3 (5)	C1B—C2B—C3B—C4B	0.6 (6)
C2—C3—C4—C5	−0.8 (5)	C2B—C3B—C4B—C5B	−1.1 (6)
C3—C4—C5—C6	1.1 (5)	C3B—C4B—C5B—C6B	0.9 (6)
C3—C4—C5—S5	−177.7 (2)	C4B—C5B—C6B—C1B	−0.3 (6)
S5—C5—C6—C1	179.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O72	0.93 (4)	1.69 (4)	2.553 (4)	153 (4)
N8A—H81A···O71^i	0.95 (4)	1.87 (4)	2.786 (4)	163 (3)
N8A—H82A···O72^ii	0.92 (4)	1.81 (4)	2.697 (4)	161 (3)
N8A—H83A···O71	0.92 (4)	2.20 (5)	3.063 (4)	157 (3)
N8B—H81B···O52^iii	0.90 (4)	2.21 (4)	3.074 (5)	160 (4)
N8B—H81B···O53^iii	0.90 (4)	2.38 (4)	3.094 (5)	137 (3)
N8B—H82B···O51^iv	0.91 (5)	2.49 (4)	2.961 (5)	113 (3)
N8B—H82B···O53^v	0.91 (5)	1.95 (4)	2.814 (5)	159 (4)
N8B—H83B···O52	0.97 (6)	1.85 (6)	2.818 (5)	176 (6)
C6—H6···O51	0.95	2.56	2.941 (4)	104
C6B—H6B···O52	0.95	2.47	3.353 (5)	154

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