In the title compound, C
4H
15N
32+·2C
6H
3Cl
2O
3S
−, 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.
Supporting information
CCDC reference: 282580
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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.
Crystal data top
C4H15N32+·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) Å3 | 0.30 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.034 | w = [1-(Fo-Fc)2/6σ2(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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H7···O3i | 0.89 | 2.08 | 2.9242 (19) | 158 |
N1—H8···O5i | 0.84 | 2.02 | 2.8475 (19) | 167 |
N1—H9···O2 | 0.88 | 1.99 | 2.830 (2) | 160 |
N2—H14···O5ii | 0.94 | 2.18 | 3.1163 (19) | 170 |
N3—H19···O3i | 0.84 | 2.08 | 2.854 (2) | 155 |
N3—H20···O6iii | 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. |