Imino­diethyl­enediaminium bis(2,5-di­chloro­benzene­sulfonate)

In the title compound, C₄H₁₅N₃²⁺·2C₆H₃Cl₂O₃S⁻, the bis(2-ammonio­ethyl)­amine is protonated at the N atoms of both amino­ethyl groups. Crystal packing is stabilized by a network of strong N—H...O hydrogen-bond interactions involving all the ions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.034
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O4      ..       3.26 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C6 H3 Cl2 O3 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C4H15N3^2+·2C6H3Cl2O3S^−	F(000) = 1144.00
Mr = 557.29	Dx = 1.602 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19169 reflections
a = 12.924 (4) Å	θ = 3.0–27.5°
b = 8.644 (3) Å	µ = 0.73 mm^−1
c = 21.250 (5) Å	T = 173 K
β = 103.25 (2)°	Cube, colourless
V = 2310.8 (13) Å^3	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4061 reflections with I > 3σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.020
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→14
Tmin = 0.776, Tmax = 0.803	k = −11→11
22603 measured reflections	l = −27→27
5288 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.034	w = [1-(Fo-Fc)^2/6σ^2(F)]^2/[3.30T0(x)-0.458T1(x) + 2.17T2(x)] where Ti are Chebychev polynomials and x = Fc/Fmax (Watkin, 1994; Prince, 1982)
S = 1.03	(Δ/σ)max = 0.001
5288 reflections	Δρmax = 0.47 e Å^−3
280 parameters	Δρmin = −0.26 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

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

	x	y	z	Uiso*/Ueq
N1	0.22891 (11)	0.70628 (17)	0.28583 (7)	0.0252 (4)
N2	0.04822 (12)	0.84415 (17)	0.20428 (7)	0.0272 (4)
N3	0.05314 (12)	0.72501 (18)	0.07701 (7)	0.0277 (4)
C13	0.16544 (15)	0.8249 (2)	0.31085 (9)	0.0311 (5)
C14	0.05188 (15)	0.8160 (2)	0.27257 (9)	0.0319 (5)
C15	−0.04623 (14)	0.7827 (2)	0.16050 (10)	0.0337 (6)
C16	−0.03989 (15)	0.8060 (2)	0.09107 (9)	0.0327 (5)
Cl1	0.29014 (3)	0.54049 (5)	0.43470 (2)	0.0293 (1)
Cl2	−0.04546 (4)	0.17606 (7)	0.54363 (2)	0.0433 (2)
S1	0.13031 (3)	0.29271 (5)	0.34132 (2)	0.0222 (1)
O1	0.04600 (10)	0.18324 (15)	0.31895 (6)	0.0292 (4)
O2	0.11548 (11)	0.43852 (16)	0.30693 (6)	0.0349 (4)
O3	0.23540 (10)	0.22671 (17)	0.34492 (6)	0.0330 (4)
C1	0.12607 (13)	0.33458 (19)	0.42314 (7)	0.0213 (4)
C2	0.19421 (13)	0.4374 (2)	0.46254 (8)	0.0246 (5)
C3	0.18895 (16)	0.4596 (2)	0.52619 (9)	0.0334 (5)
C4	0.11508 (17)	0.3795 (3)	0.55153 (9)	0.0368 (6)
C5	0.04744 (14)	0.2782 (2)	0.51242 (9)	0.0297 (5)
C6	0.05174 (13)	0.2543 (2)	0.44857 (8)	0.0252 (5)
Cl3	−0.19851 (4)	0.47077 (6)	0.00785 (2)	0.0377 (1)
Cl4	−0.19700 (5)	0.41523 (8)	0.29959 (3)	0.0506 (2)
S2	−0.00955 (3)	0.27529 (5)	0.10416 (2)	0.0215 (1)
O4	0.05186 (11)	0.40220 (16)	0.08725 (7)	0.0366 (4)
O5	0.04887 (9)	0.18694 (14)	0.15895 (6)	0.0276 (3)
O6	−0.05627 (11)	0.17791 (15)	0.04937 (6)	0.0315 (4)
C7	−0.11804 (13)	0.36105 (19)	0.13046 (8)	0.0223 (4)
C8	−0.19795 (14)	0.4436 (2)	0.08882 (9)	0.0274 (5)
C9	−0.27928 (15)	0.5124 (2)	0.11160 (10)	0.0358 (6)
C10	−0.28073 (15)	0.5021 (3)	0.17630 (11)	0.0377 (6)
C11	−0.20022 (15)	0.4225 (2)	0.21724 (9)	0.0328 (5)
C12	−0.11930 (14)	0.3498 (2)	0.19540 (8)	0.0263 (5)
H7	0.2213	0.7180	0.2433	0.0500*
H8	0.2928	0.7116	0.3061	0.0500*
H9	0.2088	0.6123	0.2925	0.0500*
H10	0.1947	0.9300	0.3054	0.0408*
H11	0.1691	0.8055	0.3577	0.0408*
H12	0.0082	0.8952	0.2890	0.0419*
H13	0.0231	0.7105	0.2776	0.0419*
H14	0.0473	0.9511	0.1954	0.0500*
H15	−0.1108	0.8362	0.1683	0.0436*
H16	−0.0510	0.6695	0.1692	0.0436*
H17	−0.0330	0.9192	0.0832	0.0400*
H18	−0.1060	0.7655	0.0616	0.0400*
H19	0.1091	0.7531	0.1027	0.0500*
H20	0.0574	0.7399	0.0399	0.0500*
H21	0.0484	0.6213	0.0809	0.0500*
H1	0.23928	0.5329	0.55410	0.0420*
H2	0.11042	0.3954	0.59741	0.0470*
H3	0.00148	0.1802	0.42102	0.0333*
H4	−0.33700	0.5692	0.08090	0.0471*
H5	−0.33894	0.5512	0.19323	0.0508*
H6	−0.06269	0.2910	0.22606	0.0342*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0253 (7)	0.0268 (7)	0.0234 (7)	−0.0002 (6)	0.0056 (5)	0.0037 (6)
N2	0.0282 (7)	0.0220 (7)	0.0320 (8)	−0.0003 (6)	0.0080 (6)	0.0033 (6)
N3	0.0319 (8)	0.0252 (7)	0.0243 (7)	−0.0015 (6)	0.0029 (6)	0.0008 (6)
C13	0.0400 (10)	0.0282 (9)	0.0265 (8)	0.0013 (8)	0.0104 (7)	−0.0023 (7)
C14	0.0349 (9)	0.0292 (9)	0.0355 (9)	0.0043 (7)	0.0162 (8)	0.0008 (7)
C15	0.0260 (9)	0.0340 (10)	0.0420 (10)	−0.0003 (8)	0.0097 (7)	−0.0034 (8)
C16	0.0287 (9)	0.0277 (9)	0.0370 (10)	0.0034 (7)	−0.0020 (7)	0.0012 (8)
Cl1	0.0280 (2)	0.0303 (2)	0.0284 (2)	−0.0107 (2)	0.0041 (2)	0.0022 (2)
Cl2	0.0432 (3)	0.0551 (3)	0.0393 (3)	−0.0157 (2)	0.0254 (2)	−0.0037 (2)
S1	0.0233 (2)	0.0251 (2)	0.0182 (2)	−0.0039 (2)	0.0044 (1)	0.0002 (2)
O1	0.0328 (7)	0.0302 (7)	0.0240 (6)	−0.0081 (5)	0.0050 (5)	−0.0024 (5)
O2	0.0428 (8)	0.0320 (7)	0.0264 (6)	−0.0091 (6)	0.0007 (5)	0.0061 (5)
O3	0.0283 (6)	0.0467 (8)	0.0255 (6)	0.0010 (6)	0.0093 (5)	−0.0053 (6)
C1	0.0210 (7)	0.0230 (8)	0.0201 (7)	0.0005 (6)	0.0053 (6)	−0.0003 (6)
C2	0.0225 (8)	0.0247 (8)	0.0267 (8)	−0.0030 (6)	0.0059 (6)	0.0008 (6)
C3	0.0362 (9)	0.0360 (10)	0.0279 (9)	−0.0104 (8)	0.0069 (7)	−0.0087 (8)
C4	0.0435 (11)	0.0447 (12)	0.0254 (9)	−0.0080 (9)	0.0146 (8)	−0.0071 (8)
C5	0.0276 (8)	0.0347 (9)	0.0305 (9)	−0.0048 (7)	0.0145 (7)	−0.0010 (8)
C6	0.0235 (8)	0.0268 (8)	0.0262 (8)	−0.0040 (6)	0.0075 (6)	−0.0028 (7)
Cl3	0.0398 (2)	0.0431 (3)	0.0281 (2)	0.0157 (2)	0.0037 (2)	0.0060 (2)
Cl4	0.0597 (3)	0.0634 (4)	0.0377 (3)	−0.0064 (3)	0.0296 (2)	−0.0095 (2)
S2	0.0234 (2)	0.0193 (2)	0.0223 (2)	0.0025 (2)	0.0067 (1)	0.0015 (2)
O4	0.0355 (7)	0.0259 (6)	0.0551 (9)	0.0025 (6)	0.0242 (6)	0.0073 (6)
O5	0.0264 (6)	0.0289 (6)	0.0264 (6)	0.0044 (5)	0.0037 (5)	0.0023 (5)
O6	0.0396 (7)	0.0285 (7)	0.0243 (6)	0.0076 (5)	0.0033 (5)	−0.0031 (5)
C7	0.0204 (7)	0.0200 (8)	0.0271 (8)	−0.0018 (6)	0.0067 (6)	−0.0026 (6)
C8	0.0250 (8)	0.0274 (9)	0.0294 (8)	0.0003 (7)	0.0056 (7)	−0.0012 (7)
C9	0.0246 (8)	0.0376 (11)	0.0447 (11)	0.0053 (8)	0.0071 (8)	−0.0019 (9)
C10	0.0289 (9)	0.0380 (10)	0.0513 (12)	−0.0007 (8)	0.0195 (8)	−0.0088 (9)
C11	0.0339 (9)	0.0350 (10)	0.0340 (9)	−0.0084 (8)	0.0170 (8)	−0.0075 (8)
C12	0.0254 (8)	0.0267 (8)	0.0278 (8)	−0.0048 (7)	0.0079 (6)	−0.0026 (7)

Geometric parameters (Å, º)

Cl1—C2	1.7371 (18)	C13—H10	1.00
Cl2—C5	1.7395 (19)	C14—H13	1.00
Cl3—C8	1.7349 (19)	C14—H12	1.00
Cl4—C11	1.742 (2)	C15—H15	1.00
S1—O1	1.4392 (14)	C15—H16	1.00
S1—O2	1.4475 (14)	C16—H18	1.00
S1—O3	1.4589 (14)	C16—H17	1.00
S1—C1	1.7891 (15)	C1—C6	1.391 (2)
S2—O4	1.4468 (15)	C1—C2	1.389 (2)
S2—O5	1.4512 (13)	C2—C3	1.383 (3)
S2—O6	1.4513 (13)	C3—C4	1.384 (3)
S2—C7	1.7853 (18)	C4—C5	1.374 (3)
N1—C13	1.486 (2)	C5—C6	1.386 (2)
N2—C14	1.462 (2)	C3—H1	1.00
N2—C15	1.455 (2)	C4—H2	1.00
N3—C16	1.480 (2)	C6—H3	1.00
N1—H9	0.88	C7—C8	1.393 (2)
N1—H8	0.84	C7—C12	1.387 (2)
N1—H7	0.89	C8—C9	1.388 (3)
N2—H14	0.94	C9—C10	1.382 (3)
N3—H19	0.84	C10—C11	1.378 (3)
N3—H21	0.90	C11—C12	1.388 (3)
N3—H20	0.81	C9—H4	1.00
C13—C14	1.508 (3)	C10—H5	1.00
C15—C16	1.510 (3)	C12—H6	1.00
C13—H11	1.00
O1—S1—C1	105.34 (8)	C16—C15—H16	109.3
O1—S1—O2	113.78 (8)	H15—C15—H16	109.4
O1—S1—O3	112.67 (8)	H17—C16—H18	109.5
O3—S1—C1	105.29 (8)	N3—C16—H17	108.7
O2—S1—O3	112.39 (8)	C15—C16—H17	108.8
O2—S1—C1	106.53 (8)	C15—C16—H18	109.6
O4—S2—O5	112.59 (8)	N3—C16—H18	109.0
O5—S2—O6	112.50 (8)	C2—C1—C6	118.96 (14)
O4—S2—O6	113.06 (8)	S1—C1—C2	123.98 (13)
O4—S2—C7	106.13 (8)	S1—C1—C6	117.03 (12)
O5—S2—C7	105.59 (8)	Cl1—C2—C3	117.44 (14)
O6—S2—C7	106.25 (8)	C1—C2—C3	120.79 (16)
C14—N2—C15	113.93 (15)	Cl1—C2—C1	121.77 (13)
C13—N1—H9	112.0	C2—C3—C4	120.25 (17)
C13—N1—H8	109.8	C3—C4—C5	118.90 (17)
C13—N1—H7	110.0	C4—C5—C6	121.62 (17)
H8—N1—H9	105.1	Cl2—C5—C6	118.92 (14)
H7—N1—H9	107.6	Cl2—C5—C4	119.46 (15)
H7—N1—H8	112.3	C1—C6—C5	119.49 (16)
C15—N2—H14	105.0	C4—C3—H1	119.9
C14—N2—H14	111.0	C2—C3—H1	119.8
H19—N3—H20	110.3	C3—C4—H2	120.8
C16—N3—H21	112.0	C5—C4—H2	120.3
C16—N3—H19	110.6	C5—C6—H3	120.1
C16—N3—H20	111.1	C1—C6—H3	120.4
H20—N3—H21	105.5	S2—C7—C8	122.35 (13)
H19—N3—H21	107.2	S2—C7—C12	118.13 (13)
N1—C13—C14	108.70 (14)	C8—C7—C12	119.46 (16)
N2—C14—C13	109.46 (16)	Cl3—C8—C7	122.23 (14)
N2—C15—C16	110.53 (15)	Cl3—C8—C9	117.17 (14)
N3—C16—C15	111.27 (15)	C7—C8—C9	120.57 (17)
N1—C13—H10	109.4	C8—C9—C10	120.22 (18)
H10—C13—H11	109.5	C9—C10—C11	118.68 (19)
C14—C13—H11	110.3	Cl4—C11—C10	119.54 (16)
N1—C13—H11	109.7	Cl4—C11—C12	118.24 (14)
C14—C13—H10	109.3	C10—C11—C12	122.20 (18)
N2—C14—H13	109.2	C7—C12—C11	118.84 (16)
H12—C14—H13	109.5	C8—C9—H4	119.6
C13—C14—H12	109.5	C10—C9—H4	120.2
N2—C14—H12	109.9	C9—C10—H5	120.9
C13—C14—H13	109.2	C11—C10—H5	120.4
C16—C15—H15	109.5	C7—C12—H6	120.7
N2—C15—H15	109.6	C11—C12—H6	120.5
N2—C15—H16	108.5
O3—S1—C1—C6	−116.42 (14)	C2—C1—C6—C5	−0.2 (3)
O2—S1—C1—C2	−58.14 (17)	C1—C2—C3—C4	−0.2 (3)
O1—S1—C1—C2	−179.30 (15)	Cl1—C2—C3—C4	−179.24 (16)
O1—S1—C1—C6	2.88 (15)	C2—C3—C4—C5	−0.1 (3)
O2—S1—C1—C6	124.04 (14)	C3—C4—C5—C6	0.2 (3)
O3—S1—C1—C2	61.41 (17)	C3—C4—C5—Cl2	179.73 (16)
O4—S2—C7—C12	−110.84 (15)	Cl2—C5—C6—C1	−179.63 (13)
O4—S2—C7—C8	66.33 (16)	C4—C5—C6—C1	−0.1 (3)
O5—S2—C7—C8	−173.94 (14)	S2—C7—C8—Cl3	−0.3 (2)
O5—S2—C7—C12	8.89 (16)	S2—C7—C8—C9	−178.09 (14)
O6—S2—C7—C8	−54.26 (16)	C12—C7—C8—Cl3	176.86 (14)
O6—S2—C7—C12	128.57 (14)	C12—C7—C8—C9	−1.0 (3)
C14—N2—C15—C16	−175.75 (14)	S2—C7—C12—C11	176.80 (14)
C15—N2—C14—C13	157.89 (14)	C8—C7—C12—C11	−0.5 (3)
N1—C13—C14—N2	−59.56 (18)	Cl3—C8—C9—C10	−176.71 (16)
N2—C15—C16—N3	60.72 (18)	C7—C8—C9—C10	1.2 (3)
S1—C1—C2—C3	−177.50 (14)	C8—C9—C10—C11	0.0 (3)
S1—C1—C2—Cl1	1.5 (2)	C9—C10—C11—Cl4	177.14 (16)
S1—C1—C6—C5	177.78 (13)	C9—C10—C11—C12	−1.4 (3)
C6—C1—C2—Cl1	179.30 (13)	Cl4—C11—C12—C7	−176.90 (14)
C6—C1—C2—C3	0.3 (3)	C10—C11—C12—C7	1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O3^i	0.89	2.08	2.9242 (19)	158
N1—H8···O5^i	0.84	2.02	2.8475 (19)	167
N1—H9···O2	0.88	1.99	2.830 (2)	160
N2—H14···O5^ii	0.94	2.18	3.1163 (19)	170
N3—H19···O3^i	0.84	2.08	2.854 (2)	155
N3—H20···O6^iii	0.81	2.02	2.823 (2)	168
N3—H21···O4	0.90	1.90	2.799 (2)	174

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