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The title compound {systematic name: trimeth­yl[2-({4-oxo-4-[2-(trimethyl­aza­nium­yl)eth­oxy]butano­yl}­oxy)eth­yl]aza­nium diiodide}, C14H30N2O42+·2I, is a salt of the succinylcholinium cation. There is one formula unit in the asymmetric unit, represented by two anions and two halves of two cations which lie on centres of inversion. The component species are stabilized by electrostatic inter­actions, and C—H...I and C—H...O hydrogen bonds are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111033245/bm3107sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111033245/bm3107Isup2.hkl
Contains datablock I

CCDC reference: 851742

Comment top

[AUTHOR: cation/molecule have been standardised to cation in the following.] Succinylcholine is used as a quaternary skeletal muscle relaxant. It is a paralytic drug used to induce muscle relaxation and short-term paralysis, usually to facilitate tracheal intubation (Thesleff, 1952). Succinylcholine iodide is used in surgical, anaesthetic and other procedures in which a brief period of muscle relaxation is called for.

Succinylcholine diiodide, (1), exists in two polymorphic forms, as revealed by IR spectroscopy and X-ray powder diffraction. Polymorph I crystallizes in the space group P21 and its crystal structure was solved by Jensen (1970), who studied compounds acting as neuromuscular blocking agents. The newly prepared previously unknown polymorph II is the subject of this article (Fig. 1). Unlike polymorph I, polymorph II is centrosymmetric. The crystals we isolated are cube-like and colourless, while polymorph I forms elongated needles. Jensen (1970) pointed to the ionic forces as the dominant feature in the structural packing.

[AUTHOR: Please check re-wording.] The succinylcholium cation contains a 12-membered chain with no rings or cyclo formations present. The central part of the chain is formed by succinyl and the peripheral part by choline (trimethylethanaminium); together, they constitute the cationic part of the structure, with the iodide anions filling the voids between the chains.

The single-crystal structure of the title compound is built up of discrete moieties in the monoclinic space group P21/c, with one formula unit in the asymmetric unit formed by the halves of two cations. The mid-point of the bond connecting the two C1A atoms in the chain of cation A lies on a centre of inversion, with a similar situation for C1B atoms in cation B. The two half-cations in the asymmetric unit are nearly identical with respect to both the conformation and the bond lengths and angles.

Polymorph II displays an S shape for the molecular chain which is apparent when viewed down the a axis (Fig. 2). This is quite unlike the U shape adopted by cations of the noncentrosymmetric polymorph I (Jensen, 1970). The S shape can be converted into the U form by two operations, each applied to either half of the cation: one half of the cation is transformed by rotation around the C1A—C2A bond by approximately 180°, and the other half by reflection through the mirror plane approximately perpendicular to the C1Ai—C1A—C2A plane [symmetry code: (i) 1 - x, 1 - y, 2 - z].

There is good agreement with regard to bond lengths. The C—C, C—O and C—N distances are very similar to those in the polymorph I (Frydenvang & Jensen, 1996). The differences between the two polymorphs include the conformation of the H atoms on atoms C1 (both A and B) with respect to atom O1 of the carbonyl group: cis in polymorph I and trans in polymorph II. The C1i—C1—C2—O1 [symmetry code: (i) 1 - x, 1 - y, 2 - z for cation A, 2 - x, 1 - y, -z for cation B] torsion angles in polymorph I and the corresponding angles in polymorph II differ by 146 and 157° for cations A and B?, respectively.

The conformational flexibility of the succinylcholine moiety is shown in the torsion angles of the molecular chain as displayed by various succinylcholine structures discussed below. The torsion angles C2B—O2B—C3B—C4B and C2A—O2A—-C3A—C4A are 79.5 (2) and 79.9 (3)°, respectively, with the corresponding angles in polymorph I being 92.0 and 88.2°. The section of the chain represented by O2B—C3B—C4B—N1B and O2A—C3A—C4A—N1A shows even smaller discrepancies: 84.2 (2) and 87.8 (3)° in polymorph II, versus 80.2 and 79.4° in polymorph I.

The centrosymmetric structures of succinylcholinium cations have the central sequence of the chain marked by C3 atoms (i.e. C3—O2—C2—C1—C1i—C2i—O2i—C3i) with very similar torsion angles. The difference appears when moving to the peripheral part of the chain at the torsion angle C2—O2—C3–C4, showing that the flexibility occurs mainly at the O2—C3—C4 sequence and therefore the cholinium moiety in centrosymmetric structures may assume different conformations. All centrosymmetric succinylcholinium structures have these angles between 159 and 175°, with the exception of the structure of polymorph II, where this angle is 79.5°. Another difference within the centrosymmetric structures is that some of them [Cambridge Structural Database (CSD; Allen, 2002) refcodes SUCPIC10 (Jensen, 1975) and VALVOU (Kazheva et al., 2002)] have a cis conformation of the H atoms on atom C1 with respect to carbonyl atom O1, while others (polymorph II, this paper; SUCCHO, Jensen, 1976; SUCHLO, Jensen, 1971; VALVUA, Kazheva et al., 2002) assume a trans conformation. The structures with a cis conformation of this sequence have values of the C1i—C1—C2—O1 torsion angle of 159 (VALVOU) and 178.5° (SUCPI10), with this angle being between 5 and 10° in the trans structures.

A search of the CSD shows that all succinylcholine structures which are centrosymmetric (in space groups P21/c or P1) and where their centre of inversion lies in the centre of the chain (cation) display an S shape for the cation and torsion angles C2i—C1i—C1—C2 (both A and B) = 180°. There is one centrosymmetric structure which does not have the centre of inversion in the centre of the chain (VALVUA). It displays a distorted S shape with an acceptable torsion angle of 163.9(s.u.??)°, the structure being characterictic of an excess of iodide relative to the succinylcholine moiety. The only known noncentrosymmetric succinylcholine structure is that of polymorph I (SUCHOL01; Jensen, 1970).

Similarly to polymorph I, the structure of polymorph II is stabilized by electrostatic interactions, and ionic forces are the dominant feature (Frydenvang & Jensen, 1993). There are two systems of hydrogen-bond interactions: C—H···O and C—H···I (Fig. 3). While the former can be regarded as typical non-classical hydrogen bonds, the long C—H···I interactions must be considered weak hydrogen bonds. If the H···I distance is set to the sum of the relevant van der Waals radii plus 0.2 (3.38 Å; Bondi, 1964), there are nine interactions on I1 and nine on I2, showing that the environment of both iodide ions is similar. If it is set to the sum of the van der Waals radii minus 0.12 (Jeffrey criterium, reference?; in this case 3.06 Å), only two interactions appear on I1 and none on I2.

The geometric parameters describing the C—H···I interactions in polymorph II are in accordance with the mean values of Desiraju & Steiner (1999). The observed values (average of 18 interactions within the H···I limit of 3.38 Å) are as follows: H···I = 3.2 Å compared with 3.16 (1) Å, C···I = 4.10 Å compared with 4.15 (1) Å and C—H···I angle = 152.9° compared with 152.8 (6)°.

For the purpose of clarity, Table 1 features only two C—H···I hydrogen bonds as defined by the IUCr limit and two intermolecular C—H···O bonds: one strong with an H···A distance of 2.30 Å, the other weaker with a value of 2.51 Å. Similar contacts were described and summarized by Taylor & Kennard (1982).

There is much less in the literature regarding (ultra-)long C—H···I interactions. Similar H···I distances were observed in the structure of Dach Pt iodide, with distances between 2.97 and 3.10 Å (Pažout et al., 2011). The same C—H···I interactions, with distances between 2.93 and 3.14 Å, are found in the structure of polymorph I, although Jensen (1970) did not consider them to be hydrogen bonds and mentioned C—I close contacts between 3.58 and 3.97 Å instead. Similar interactions were also reported by Frydenvang & Jensen (1996). The spatial arrangement of the chains of cations (Fig. 5) shows horizontal B cations and inclined A cations.

[AUTHOR: Please supply response for VRF form in CIF regarding outliers]

Related literature top

For related literature, see: Allen (2002); Bondi (1964); Desiraju & Steiner (1999); Frydenvang & Jensen (1993, 1996); Jensen (1970, 1971, 1975, 1976); Kazheva et al. (2002); Pažout et al. (2011); Taylor & Kennard (1982); Thesleff (1952).

Experimental top

The title compound (Fig. 1) was obtained as a gift from the pharmaceutical company Interpharma, Prague, Czech Republic. Recrystallisation from which solvent to obtain new polymorph?

Refinement top

[[AUTHOR: Some of the text supplied below was not originally correct; please check the revised version.]]

A cube-like crystal was first measured on a diffractometer with Cu radiation, but even longer exposure times and the analytical absorption correction did not result in data quality with Rint under 0.20. Therefore, the crystal was measured with Mo radiation, followed by a meticulous absorption correction consisting of refinement of the crystal shape accompanied by a multi-scan correction. The final Rint value was 0.018.

All H atoms were first placed geometrically and then refined using a riding model, with C—H = 0.96 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: ORTEP-3 (Farrugia, 1999) and Mercury (Version 2.3; Macrae et al., 2008); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
Fig. 1. The molecular structure of polymorph II, showing the atom-numbering scheme. Displacment ellipsoids are drawn at the 50% probability level. Unlabelled atoms are related to labelled atoms by the symmetry operators ? [Please complete] [Labels overlap some atoms. Please provide a better version]

Fig. 2. A view of the eight hydrogen bonds formed by two C—H···O and six long C—H···I interactions. Only H···I distances of less than 3.15 Å are considered.

Fig. 3. Five hydrogen-bond interactions at the iodide anion I1. [Figure appears to be missing - please supply file]

Fig. 4. The chessboard packing of the succinylcholine molecules [##AUTHOR: succinylcholinium cations?] of polymorph II. Type A cations are inclined and type B cations are horizontal in this view.
trimethyl[2-({4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl}oxy)ethyl]azanium diiodide top
Crystal data top
C14H30N2O42+·2IF(000) = 1064
Mr = 544.2Dx = 1.713 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 23198 reflections
a = 11.6138 (2) Åθ = 2.9–29.3°
b = 13.0673 (3) ŵ = 3.00 mm1
c = 13.9152 (3) ÅT = 151 K
β = 92.6170 (15)°Block, colourless
V = 2109.58 (8) Å30.30 × 0.28 × 0.26 mm
Z = 4
Data collection top
Oxford Xcalibur Atlas Gemini Ultra
diffractometer
5358 independent reflections
Radiation source: Enhance (Mo) X-ray Source4954 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 10.3784 pixels mm-1θmax = 29.4°, θmin = 2.9°
ω scansh = 1415
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2008)
k = 1717
Tmin = 0.820, Tmax = 1.000l = 1819
31136 measured reflections
Refinement top
Refinement on F120 constraints
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.038Weighting scheme based on measured s.u.'s w = 1/[σ2(F) + 0.0001F2]
S = 2.41(Δ/σ)max = 0.031
5358 reflectionsΔρmax = 0.43 e Å3
199 parametersΔρmin = 0.33 e Å3
0 restraints
Crystal data top
C14H30N2O42+·2IV = 2109.58 (8) Å3
Mr = 544.2Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.6138 (2) ŵ = 3.00 mm1
b = 13.0673 (3) ÅT = 151 K
c = 13.9152 (3) Å0.30 × 0.28 × 0.26 mm
β = 92.6170 (15)°
Data collection top
Oxford Xcalibur Atlas Gemini Ultra
diffractometer
5358 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2008)
4954 reflections with I > 3σ(I)
Tmin = 0.820, Tmax = 1.000Rint = 0.018
31136 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.038H-atom parameters constrained
S = 2.41Δρmax = 0.43 e Å3
5358 reflectionsΔρmin = 0.33 e Å3
199 parameters
Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.34a (release 20-07-2010 CrysAlis171 .NET) (compiled Jul 20 2010,14:26:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.476572 (14)0.916050 (13)0.233380 (12)0.02253 (6)
I20.006725 (15)0.293705 (14)0.430571 (12)0.02508 (6)
O2B0.84761 (15)0.50597 (13)0.16706 (12)0.0194 (5)
O1B1.04090 (16)0.50129 (15)0.17714 (13)0.0253 (6)
O1A0.53984 (17)0.68792 (16)1.00856 (15)0.0295 (6)
O2A0.34611 (16)0.68383 (15)0.99999 (13)0.0243 (6)
N1A0.25763 (17)0.84282 (16)0.83040 (14)0.0186 (6)
N1B0.76816 (17)0.69613 (16)0.29736 (15)0.0199 (6)
C3B0.8489 (2)0.5172 (2)0.27099 (17)0.0207 (7)
C6B0.7023 (2)0.6902 (2)0.2023 (2)0.0263 (8)
C2B0.9511 (2)0.50121 (18)0.12846 (18)0.0175 (7)
C4B0.8719 (2)0.62743 (19)0.29975 (17)0.0184 (7)
C5A0.1855 (2)0.7486 (2)0.8313 (2)0.0256 (8)
C6A0.2915 (2)0.8604 (2)0.72916 (18)0.0261 (8)
C7A0.1914 (2)0.9330 (2)0.8633 (2)0.0278 (9)
C3A0.3462 (2)0.7933 (2)0.99497 (19)0.0252 (8)
C2A0.4517 (2)0.6397 (2)1.00463 (17)0.0214 (7)
C5B0.6903 (2)0.6701 (3)0.3770 (2)0.0332 (9)
C4A0.3656 (2)0.8302 (2)0.89318 (18)0.0216 (7)
C7B0.8103 (2)0.8040 (2)0.3128 (2)0.0292 (9)
C1A0.4428 (2)0.5248 (2)1.00497 (18)0.0245 (8)
C1B0.9409 (2)0.49450 (19)0.02185 (17)0.0213 (7)
H1C3B0.9077730.4740830.2999350.0248*
H2C3B0.7759410.4960020.2939680.0248*
H1C6B0.7543810.6990150.1512750.0316*
H2C6B0.6654030.6247030.1960390.0316*
H3C6B0.6450570.7432490.198670.0316*
H1C4B0.9092810.6294040.3626860.022*
H2C4B0.9292360.6558110.2599630.022*
H1C5A0.2315810.6904090.8160140.0307*
H2C5A0.1557140.7397890.8939980.0307*
H3C5A0.122590.755040.7844570.0307*
H1C6A0.3423110.9182840.7273940.0314*
H2C6A0.3301050.8008360.7063290.0314*
H3C6A0.2237820.8734850.6888730.0314*
H1C7A0.2390830.9929680.86210.0334*
H2C7A0.1243740.9427760.8213440.0334*
H3C7A0.1680490.9214010.9277140.0334*
H1C3A0.405740.8199011.0380910.0302*
H2C3A0.2738560.8190451.0154210.0302*
H1C5B0.7313970.6785450.4378980.0398*
H2C5B0.6245110.7146580.3738210.0398*
H3C5B0.6651190.6003670.3701890.0398*
H1C4A0.4072530.89370.8958710.0259*
H2C4A0.4172140.7842820.8627950.0259*
H1C7B0.8574070.8074440.3712290.035*
H2C7B0.8548840.8244390.259630.035*
H3C7B0.7454950.8491040.3174110.035*
H1C1A0.4103730.5026651.0637170.0294*
H2C1A0.3909060.5031220.9532370.0294*
H1C1B0.8904930.5474780.0027770.0255*
H2C1B0.9075810.4298310.0032930.0255*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02221 (11)0.02083 (11)0.02428 (10)0.00244 (6)0.00178 (7)0.00228 (6)
I20.02927 (11)0.02732 (11)0.01870 (10)0.00356 (7)0.00142 (7)0.00028 (7)
O2B0.0200 (9)0.0204 (9)0.0180 (8)0.0017 (7)0.0025 (7)0.0037 (7)
O1B0.0217 (10)0.0343 (11)0.0196 (9)0.0053 (8)0.0012 (7)0.0016 (8)
O1A0.0274 (11)0.0294 (11)0.0312 (11)0.0036 (8)0.0020 (8)0.0043 (9)
O2A0.0270 (10)0.0236 (10)0.0223 (9)0.0076 (8)0.0009 (8)0.0051 (8)
N1A0.0183 (10)0.0207 (11)0.0166 (9)0.0011 (8)0.0009 (8)0.0033 (8)
N1B0.0163 (10)0.0208 (11)0.0223 (11)0.0005 (8)0.0010 (8)0.0045 (9)
C3B0.0237 (13)0.0215 (14)0.0169 (11)0.0008 (10)0.0021 (10)0.0016 (10)
C6B0.0212 (13)0.0262 (15)0.0306 (14)0.0028 (11)0.0095 (11)0.0051 (12)
C2B0.0197 (12)0.0130 (11)0.0198 (12)0.0008 (9)0.0021 (10)0.0019 (9)
C4B0.0141 (11)0.0212 (13)0.0195 (11)0.0012 (9)0.0015 (9)0.0018 (10)
C5A0.0231 (14)0.0284 (15)0.0250 (13)0.0076 (11)0.0014 (11)0.0012 (12)
C6A0.0283 (14)0.0319 (16)0.0182 (12)0.0026 (11)0.0015 (10)0.0064 (11)
C7A0.0274 (15)0.0279 (15)0.0278 (14)0.0090 (11)0.0026 (12)0.0029 (12)
C3A0.0317 (15)0.0228 (14)0.0204 (12)0.0105 (11)0.0066 (11)0.0028 (10)
C2A0.0266 (14)0.0238 (14)0.0140 (11)0.0066 (11)0.0012 (10)0.0040 (10)
C5B0.0258 (15)0.0393 (18)0.0357 (16)0.0041 (13)0.0148 (12)0.0139 (14)
C4A0.0187 (12)0.0204 (13)0.0252 (13)0.0013 (10)0.0032 (10)0.0006 (11)
C7B0.0270 (15)0.0214 (14)0.0390 (16)0.0019 (11)0.0005 (12)0.0092 (12)
C1A0.0263 (14)0.0255 (14)0.0218 (13)0.0017 (11)0.0039 (11)0.0047 (11)
C1B0.0214 (13)0.0230 (14)0.0192 (12)0.0011 (10)0.0014 (10)0.0045 (10)
Geometric parameters (Å, º) top
O2B—C3B1.453 (3)C5A—H3C5A0.96
O2B—C2B1.340 (3)C6A—H1C6A0.96
O1B—C2B1.217 (3)C6A—H2C6A0.96
O1A—C2A1.201 (3)C6A—H3C6A0.96
O2A—C3A1.432 (3)C7A—H1C7A0.96
O2A—C2A1.354 (3)C7A—H2C7A0.96
N1A—C5A1.489 (4)C7A—H3C7A0.96
N1A—C6A1.498 (3)C3A—C4A1.523 (4)
N1A—C7A1.491 (4)C3A—H1C3A0.96
N1A—C4A1.504 (3)C3A—H2C3A0.96
N1B—C6B1.499 (3)C2A—C1A1.505 (4)
N1B—C4B1.501 (3)C5B—H1C5B0.96
N1B—C5B1.501 (4)C5B—H2C5B0.96
N1B—C7B1.505 (3)C5B—H3C5B0.96
C3B—C4B1.516 (4)C4A—H1C4A0.96
C3B—H1C3B0.96C4A—H2C4A0.96
C3B—H2C3B0.96C7B—H1C7B0.96
C6B—H1C6B0.96C7B—H2C7B0.96
C6B—H2C6B0.96C7B—H3C7B0.96
C6B—H3C6B0.96C1A—C1Ai1.492 (4)
C2B—C1B1.485 (3)C1A—H1C1A0.96
C4B—H1C4B0.96C1A—H2C1A0.96
C4B—H2C4B0.96C1B—C1Bii1.533 (4)
C5A—H1C5A0.96C1B—H1C1B0.96
C5A—H2C5A0.96C1B—H2C1B0.96
C3B—O2B—C2B115.78 (19)H2C6A—C6A—H3C6A109.4711
C3A—O2A—C2A115.1 (2)N1A—C7A—H1C7A109.4709
C5A—N1A—C6A107.9 (2)N1A—C7A—H2C7A109.4711
C5A—N1A—C7A110.6 (2)N1A—C7A—H3C7A109.4705
C5A—N1A—C4A111.06 (19)H1C7A—C7A—H2C7A109.4724
C6A—N1A—C7A109.2 (2)H1C7A—C7A—H3C7A109.4705
C6A—N1A—C4A108.38 (19)H2C7A—C7A—H3C7A109.4719
C7A—N1A—C4A109.65 (19)O2A—C3A—C4A111.2 (2)
C6B—N1B—C4B111.41 (19)O2A—C3A—H1C3A109.471
C6B—N1B—C5B109.9 (2)O2A—C3A—H2C3A109.4709
C6B—N1B—C7B108.9 (2)C4A—C3A—H1C3A109.4719
C4B—N1B—C5B111.0 (2)C4A—C3A—H2C3A109.4707
C4B—N1B—C7B107.56 (19)H1C3A—C3A—H2C3A107.6332
C5B—N1B—C7B108.1 (2)O1A—C2A—O2A123.2 (2)
O2B—C3B—C4B110.6 (2)O1A—C2A—C1A125.6 (2)
O2B—C3B—H1C3B109.4708O2A—C2A—C1A111.2 (2)
O2B—C3B—H2C3B109.4714N1B—C5B—H1C5B109.4712
C4B—C3B—H1C3B109.4714N1B—C5B—H2C5B109.4709
C4B—C3B—H2C3B109.4718N1B—C5B—H3C5B109.4711
H1C3B—C3B—H2C3B108.2858H1C5B—C5B—H2C5B109.4716
N1B—C6B—H1C6B109.4715H1C5B—C5B—H3C5B109.4713
N1B—C6B—H2C6B109.4711H2C5B—C5B—H3C5B109.4712
N1B—C6B—H3C6B109.4716N1A—C4A—C3A114.8 (2)
H1C6B—C6B—H2C6B109.471N1A—C4A—H1C4A109.4716
H1C6B—C6B—H3C6B109.4708N1A—C4A—H2C4A109.471
H2C6B—C6B—H3C6B109.4713C3A—C4A—H1C4A109.4707
O2B—C2B—O1B122.6 (2)C3A—C4A—H2C4A109.4715
O2B—C2B—C1B111.8 (2)H1C4A—C4A—H2C4A103.5293
O1B—C2B—C1B125.6 (2)N1B—C7B—H1C7B109.4705
N1B—C4B—C3B115.5 (2)N1B—C7B—H2C7B109.4712
N1B—C4B—H1C4B109.4708N1B—C7B—H3C7B109.4717
N1B—C4B—H2C4B109.4716H1C7B—C7B—H2C7B109.471
C3B—C4B—H1C4B109.4707H1C7B—C7B—H3C7B109.4711
C3B—C4B—H2C4B109.4715H2C7B—C7B—H3C7B109.4718
H1C4B—C4B—H2C4B102.6302C2A—C1A—C1Ai111.8 (2)
N1A—C5A—H1C5A109.4717C2A—C1A—H1C1A109.4708
N1A—C5A—H2C5A109.4714C2A—C1A—H2C1A109.4707
N1A—C5A—H3C5A109.4708C1Ai—C1A—H1C1A109.4719
H1C5A—C5A—H2C5A109.4716C1Ai—C1A—H2C1A109.4715
H1C5A—C5A—H3C5A109.4705H1C1A—C1A—H2C1A107.0247
H2C5A—C5A—H3C5A109.4712C2B—C1B—C1Bii111.0 (2)
N1A—C6A—H1C6A109.4708C2B—C1B—H1C1B109.4706
N1A—C6A—H2C6A109.4721C2B—C1B—H2C1B109.4711
N1A—C6A—H3C6A109.4717C1Bii—C1B—H1C1B109.4716
H1C6A—C6A—H2C6A109.471C1Bii—C1B—H2C1B109.4716
H1C6A—C6A—H3C6A109.4706H1C1B—C1B—H2C1B107.8553
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3B—H1C3B···I2iii0.963.164.055 (3)156
C3B—H2C3B···I1iv0.963.124.002 (3)154
C6B—H1C6B···I2v0.963.294.151 (3)151
C6B—H3C6B···I10.963.043.984 (3)168
C4B—H1C4B···I2vi0.963.164.080 (2)161
C5A—H2C5A···I2vii0.963.234.121 (3)155
C6A—H1C6A···I1viii0.963.053.991 (3)167
C7A—H2C7A···O1Bix0.962.313.176 (3)150
C3A—H1C3A···I1x0.963.073.926 (3)149
C5B—H2C5B···O1Axi0.962.503.184 (4)128
C5B—H3C5B···I1iv0.963.224.106 (3)154
C4A—H2C4A···I1xii0.963.274.150 (3)154
C7B—H2C7B···I2v0.963.184.082 (3)156
C1A—H1C1A···I1xiii0.963.263.980 (3)133
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y1/2, z+1/2; (v) x+1, y+1/2, z+1/2; (vi) x+1, y+1, z+1; (vii) x, y+1/2, z+3/2; (viii) x+1, y+2, z+1; (ix) x1, y+3/2, z+1/2; (x) x, y, z+1; (xi) x, y+3/2, z1/2; (xii) x, y+3/2, z+1/2; (xiii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H30N2O42+·2I
Mr544.2
Crystal system, space groupMonoclinic, P21/c
Temperature (K)151
a, b, c (Å)11.6138 (2), 13.0673 (3), 13.9152 (3)
β (°) 92.6170 (15)
V3)2109.58 (8)
Z4
Radiation typeMo Kα
µ (mm1)3.00
Crystal size (mm)0.30 × 0.28 × 0.26
Data collection
DiffractometerOxford Xcalibur Atlas Gemini Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2008)
Tmin, Tmax0.820, 1.000
No. of measured, independent and
observed [I > 3σ(I)] reflections
31136, 5358, 4954
Rint0.018
(sin θ/λ)max1)0.691
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.038, 2.41
No. of reflections5358
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.33

Computer programs: CrysAlis PRO (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2006), ORTEP-3 (Farrugia, 1999) and Mercury (Version 2.3; Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6B—H3C6B···I10.963.043.984 (3)168
C6A—H1C6A···I1i0.963.053.991 (3)167
C7A—H2C7A···O1Bii0.962.313.176 (3)150
C5B—H2C5B···O1Aiii0.962.503.184 (4)128
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y+3/2, z+1/2; (iii) x, y+3/2, z1/2.
 

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