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Acta Cryst. (2006). E62, o8-o10
https://doi.org/10.1107/S1600536805038948
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DL-Methio­nine DL-methio­ninium picrate

K. Anitha, S. Athimoolam and R. K. Rajaram
The asymmetric unit of the title compound, C5H11NO2S·C5H12NO2S+·C6H2N3O7−, is composed of two crystallographically independent methio­nine residues and a picrate anion. The methio­nine and protonated methio­ninium residues are bonded through a strong O—H...O hydrogen bond, and an inversion-related DL1 head-to-tail sequence along the a axis is observed in the zwitterion. The amino groups of two residues connect to the lone oxygen of two inversion-related picrate anions. Hydro­phobic layers are observed in the y = 0 plane.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038948/hk6032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038948/hk6032Isup2.hkl
Contains datablock I

CCDC reference: 296577

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.072
  • wR factor = 0.237
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.59 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion  S     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion  S     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.69 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C14
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C15
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        S21
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C132
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S11
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S12
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C131
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C24
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C25
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S22
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      13.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........        YES
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........      2_566
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........        151
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........    2.861(5
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........       2.26
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.90 Deg.
              C131 -C12  -C132    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.30 Deg.
              H22A -C12  -H12B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.30 Deg.
              C12  -C131 -H12B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.30 Deg.
              C131 -C14  -C132    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      16.50 Deg.
              S1   -C14  -S12     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.20 Deg.
              S1   -C14  -S11     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.00 Deg.
              S12  -C14  -S11     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       8.70 Deg.
              H14A -C14  -H14C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      23.00 Deg.
              H14B -C14  -H14D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.60 Deg.
              C15  -S1   -H15H    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.30 Deg.
              S1   -C15  -S11     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.10 Deg.
              S1   -C15  -S12     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.20 Deg.
              S11  -C15  -S12     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.90 Deg.
              H15A -C15  -H15D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      16.80 Deg.
              H15B -C15  -H15E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.90 Deg.
              H15C -C15  -H15F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       8.50 Deg.
              H15A -C15  -H15G    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.20 Deg.
              H15D -C15  -H15G    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.20 Deg.
              H15B -C15  -H15H    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              H15E -C15  -H15H    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      23.00 Deg.
              H15C -C15  -H15I    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.60 Deg.
              H15F -C15  -H15I    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       4.40 Deg.
              S2   -C24  -S22     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       1.50 Deg.
              H24A -C24  -H24E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       1.40 Deg.
              H24B -C24  -H24F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.60 Deg.
              C24  -S2   -H24D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.70 Deg.
              C24  -S21  -H24F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.20 Deg.
              C25  -S21  -H25H    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.70 Deg.
              C24  -S22  -H24D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.90 Deg.
              C25  -S22  -H25D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.20 Deg.
              C25  -S22  -H25F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       7.20 Deg.
              S22  -C25  -S2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.70 Deg.
              H25A -C25  -H25D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.60 Deg.
              H25C -C25  -H25F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       5.00 Deg.
              H25A -C25  -H25G    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.50 Deg.
              H25D -C25  -H25G    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.50 Deg.
              H25B -C25  -H25H    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       3.90 Deg.
              H25C -C25  -H25I    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.20 Deg.
              H25F -C25  -H25I    1.555   1.555   1.555


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

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

Methionine, an essential amino acid, is one of the two sulfur-containing amino acids. The side chain is quite hydrophobic and methionine is usually found buried within proteins. Methionine reacts with adenosine triphosphate to form S-adenosyl methionine, a potent donor of methyl groups in the body (Jain, 1994) and contributes to the synthesis of many important substances, like choline. The crystal structures of L-methionine (Torii & Iitaka, 1973), DL-methionine (α-form) (Mathieson, 1952), L-methionine hydrochloride (Di Blasio et al., 1977), bis(DL-methionine) dihydrogen phosphate (Bahadur, 1992), L-methionine L-methioninium perchlorate monohydrate (Sridhar et al., 2002), bis(L-methioninium) sulfate (Srinivasan et al., 2001a), L-methioninium nitrate (Pandiarajan et al., 2002) and bis(DL-methioninium) sulfate (Ramaswamy et al., 2004) have been reported. As part of studying hydrogen bonding of picrate complexes of amino acids, DL-methionine with picric acid is reported.

The asymmetric unit of the title compound, (I), contains two crystallographically independent methionine residues and a picrate anion (Fig. 1). The equality of bond distances show that the proton liberated from the picric acid is shared by both the methionine residues (Table 1). Such a type of proton sharing is also found in L-lysine L-lysinium dichloride nitrate (Srinivasan et al., 2001b). The Sδ atom in both the molecules and Cβ atom of residue A are disordered. The backbone conformation angles ψ1and ψ2 are cis and trans, respectively, for both the residues. The straight-side chain conformation angles χ1/χ2/χ3 are trans/trans/ gauche I and gauche II/ gauche I/ gauche I for residues A and B, respectively.

The picrate anion plays an important role in forming hydrogen bonds. In the picrate anion, removal of proton leads to a shortening of the C—O bond and lengthening of adjacent C—C bond distances like many other picrate complexes. In most of the picrates the ortho-related nitro groups are rotated out of the molecular plane than the para-nitro substituent (Anitha et al., 2004; Smith et al., 2004). These nitro groups are commonly involved in the hydrogen bonding. In the present case, one of the ortho-nitro groups is twisted from the plane of the ring. Such a type of twisting of these nitro groups is independent of C—N bond distances (Soriano-Garcia et al., 1978; Srikrishnan et al., 1980). The nitro O atoms, not involved in hydrogen bonding, have large Ueq values.

Both the protonated methioninium residues are bonded through a strong asymmetric O—H···O hydrogen bond forming a dimer (Table 2 and Fig. 2). In residue A, two two-centered and one chelated three-centered hydrogen bonds are observed leading to class II hydrogen-bonding pattern besides of an inversion-related DL1 head-to-tail sequence. The amino groups of two residues are connected through the lone oxygen of a picrate anion and the amino group of residue A connects O atoms of same picrate leading to a chelated three-centered hydrogen bond. Three two-centered hydrogen bonds are observed in the residue B leading to class I hydrogen-bonding pattern·The amino group of residue B connects two different picrate anion. It also connects carboxyl oxygen of inversion-related residue A and amino group of residue A connects O atom of the residue B leadingto a closed loop. The hydrophobic layers are observed along the y = 0 plane.

Experimental top

The title compound was crystallized from DL-methionine and picric acid mixture in the stoichiometric ratio of 2:1 at room temperature by the technique of slow evaporation.

Refinement top

When the crystal structure was solved, the sulfur of both the residues and Cβ of methionine residue were found to be disordered. Of these for both the sulfur, two satellite peaks were observed. Hence two more sets of data, with two different crystals drawn from different crops, were collected. This disorder was observed in these two data sets also. During refinement with isotropic thermal parameters, the occupancy of disordered atoms in both the residues were refined. These site-occupancy factors were fixed as S1 0.55, S11 0.21, S12 0.24, C131 0.35, C132 0.65, S2 0.55, S21 0.10 and S22 0.35 during anisotropic refinement. The final refinements were performed with one set of data only. All the H atoms were placed in geometrically calculated positions [0.89 (NH), 0.82 (OH), 0.93 and 0.98 (CH), 0.97 (CH2) and 0.96 Å (CH3)] and constrained to ride on their parent atoms with Uiso(H) = 1.5(1.2 for CH and CH2) Ueq(C,N,O).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 25% probability level. (The disordered atoms which have major occupancy are considered here for clarity).
[Figure 2] Fig. 2. Packing diagram of (I) viewed down the a axis. Hydrogen bonds are drawn as dashed lines. (The disordered atoms which have major occupancy are considered here for clarity).
DL-methionine DL-methioninium picrate top
Crystal data top
C5H11NO2S·C5H12NO2S+·C6H2N3O7−Z = 2
Mr = 527.53F(000) = 552
Triclinic, P1Dx = 1.469 Mg m−3
Dm = 1.460 Mg m−3
Dm measured by flotation in a mixture of carbon tetrachloride and xylene
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.076 (1) ÅCell parameters from 25 reflections
b = 12.102 (1) Åθ = 6.8–14.2°
c = 14.895 (2) ŵ = 0.29 mm−1
α = 103.90 (1)°T = 293 K
β = 97.04 (2)°Needle, yellow
γ = 101.73 (2)°0.2 × 0.15 × 0.10 mm
V = 1192.4 (3) Å3
Data collection top
Nonius MACH3 four-circle
diffractometer		2516 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω–2θ scansh = −1→8
Absorption correction: ψ scan
(North et al., 1968)		k = −14→14
Tmin = 0.943, Tmax = 0.975l = −17→17
4940 measured reflections3 standard reflections every 60 min
4217 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1091P)2 + 0.8526P]
where P = (Fo2 + 2Fc2)/3
4217 reflections(Δ/σ)max < 0.001
331 parametersΔρmax = 0.80 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C5H11NO2S·C5H12NO2S+·C6H2N3O7−γ = 101.73 (2)°
Mr = 527.53V = 1192.4 (3) Å3
Triclinic, P1Z = 2
a = 7.076 (1) ÅMo Kα radiation
b = 12.102 (1) ŵ = 0.29 mm−1
c = 14.895 (2) ÅT = 293 K
α = 103.90 (1)°0.2 × 0.15 × 0.10 mm
β = 97.04 (2)°
Data collection top
Nonius MACH3 four-circle
diffractometer		2516 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.014
Tmin = 0.943, Tmax = 0.9753 standard reflections every 60 min
4940 measured reflections intensity decay: none
4217 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.237H-atom parameters constrained
S = 1.03Δρmax = 0.80 e Å−3
4217 reflectionsΔρmin = −0.56 e Å−3
331 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.2509 (17)0.0585 (9)0.6210 (7)0.158 (4)0.55
S110.218 (4)0.0339 (18)0.5625 (13)0.111 (6)0.21
S120.196 (2)0.0260 (10)0.5974 (10)0.053 (2)0.24
S21.153 (3)0.9057 (19)0.9041 (15)0.074 (4)0.55
S211.187 (7)1.028 (4)0.868 (3)0.219 (17)*0.10
S221.171 (6)0.891 (3)0.901 (3)0.070 (5)0.35
O10.5379 (5)0.4989 (4)0.7445 (2)0.0776 (11)
O1A−0.0396 (4)0.3706 (3)0.42963 (19)0.0537 (8)
O1B−0.2265 (5)0.2605 (3)0.5002 (2)0.0691 (10)
O20.2200 (7)0.5794 (4)0.7647 (3)0.0907 (13)
O2A0.5877 (5)0.6334 (3)0.5883 (2)0.0548 (8)
O2B0.4874 (5)0.7963 (3)0.6390 (3)0.0691 (10)
O30.1344 (8)0.5922 (4)0.8995 (3)0.1067 (16)
O40.1992 (7)0.3067 (5)1.0576 (3)0.1073 (16)
O50.4230 (8)0.2122 (5)1.0373 (4)0.1134 (17)
O60.8341 (6)0.2702 (5)0.8164 (3)0.1004 (12)
O70.8363 (10)0.4007 (6)0.7498 (5)0.156 (3)
N10.2243 (7)0.5521 (4)0.8388 (3)0.0712 (12)
N20.3302 (7)0.2801 (4)1.0177 (3)0.0701 (12)
N30.7622 (8)0.3449 (6)0.7973 (4)0.1004 (12)
N110.2558 (5)0.4510 (3)0.5766 (2)0.0473 (9)
N210.8588 (5)0.6776 (3)0.7398 (2)0.0536 (9)
C10.4937 (6)0.4498 (4)0.8070 (3)0.0514 (11)
C20.3349 (7)0.4685 (4)0.8558 (3)0.0501 (10)
C30.2829 (6)0.4131 (4)0.9224 (3)0.0510 (11)
C40.3833 (7)0.3357 (4)0.9450 (3)0.0507 (11)
C50.5410 (7)0.3135 (4)0.9038 (3)0.0526 (11)
C60.5940 (6)0.3699 (4)0.8375 (3)0.0510 (11)
C11−0.0678 (6)0.3269 (4)0.4952 (3)0.0439 (10)
C120.0955 (7)0.3520 (4)0.5787 (3)0.0537 (11)
C140.1235 (15)0.1645 (8)0.6194 (9)0.157 (3)
C150.4668 (16)0.0792 (8)0.6337 (9)0.157 (3)
C210.5973 (6)0.7260 (4)0.6456 (3)0.0479 (10)
C220.7468 (6)0.7684 (4)0.7363 (3)0.0508 (11)
C230.8796 (8)0.8878 (4)0.7478 (4)0.0699 (14)
C240.9766 (9)0.9572 (5)0.8492 (4)0.0896 (19)
C251.3616 (10)0.9459 (7)0.8475 (5)0.100 (2)
C1310.118 (2)0.2552 (12)0.6108 (11)0.061 (3)*0.35
C1320.2035 (11)0.2375 (7)0.5659 (5)0.0575 (18)0.65
H2B0.39540.76440.59500.104*
H30.17920.42830.95220.061*
H50.61000.26160.92060.063*
H22A0.03530.39220.62870.064*0.35
H11A0.20520.50150.55260.071*
H11B0.33770.42380.54120.071*
H11C0.32060.48710.63480.071*
H12B0.04530.36980.63770.064*0.65
H13A0.25180.29150.64320.073*0.35
H13B0.04170.27190.66020.073*0.35
H13C0.17990.19380.50020.069*0.65
H13D0.34410.26600.58750.069*0.65
H14A0.00750.11780.57410.188*0.35
H14B0.08150.17140.67970.188*0.35
H14C0.00670.10950.57990.188*0.65
H14D0.08790.20320.67760.188*0.65
H15A0.50270.00540.62380.236*0.55
H15B0.52400.12680.69640.236*0.55
H15C0.51400.11880.58920.236*0.55
H15D0.4739−0.00080.62670.236*0.21
H15E0.55810.12900.68840.236*0.21
H15F0.49900.10230.57910.236*0.21
H15G0.52250.01220.62540.236*0.24
H15H0.46310.10930.69910.236*0.24
H15I0.54570.13870.61240.236*0.24
H21A0.94580.70070.79320.080*
H21B0.92120.66760.69120.080*
H21C0.77640.61030.73720.080*
H220.67470.77490.78870.061*
H23A0.80360.93440.72140.084*
H23B0.98230.87760.71120.084*
H24A0.87420.96060.88680.107*0.55
H24B1.03491.03700.84910.107*0.55
H24C0.90141.01480.86810.107*0.10
H24D0.94970.90190.88630.107*0.10
H24E0.87610.95980.88800.107*0.35
H24F1.03681.03730.85060.107*0.35
H25A1.47000.91920.87260.150*0.55
H25B1.39881.02970.85930.150*0.55
H25C1.32560.91010.78100.150*0.55
H25D1.43560.93510.90190.150*0.10
H25E1.44750.99290.81850.150*0.10
H25F1.30190.87090.80350.150*0.10
H25G1.47670.92260.86930.150*0.35
H25H1.38811.03000.86400.150*0.35
H25I1.32580.91520.78040.150*0.35
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.161 (8)0.193 (8)0.220 (11)0.115 (7)0.094 (7)0.154 (8)
S110.144 (13)0.058 (7)0.120 (14)0.021 (7)−0.020 (12)0.028 (10)
S120.070 (5)0.025 (3)0.060 (5)0.005 (3)−0.001 (4)0.019 (3)
S20.073 (6)0.091 (7)0.040 (4)−0.002 (6)0.002 (4)0.008 (4)
S220.072 (6)0.083 (7)0.055 (9)0.024 (4)0.003 (5)0.021 (6)
O10.062 (2)0.120 (3)0.054 (2)−0.002 (2)0.0054 (16)0.053 (2)
O1A0.0528 (18)0.076 (2)0.0418 (16)0.0186 (15)0.0100 (13)0.0296 (15)
O1B0.059 (2)0.081 (2)0.067 (2)−0.0018 (18)0.0019 (16)0.0402 (18)
O20.126 (4)0.102 (3)0.060 (2)0.053 (3)0.007 (2)0.036 (2)
O2A0.0599 (19)0.064 (2)0.0413 (16)0.0138 (15)0.0140 (14)0.0137 (15)
O2B0.063 (2)0.066 (2)0.070 (2)0.0189 (18)−0.0085 (17)0.0101 (17)
O30.144 (4)0.128 (4)0.079 (3)0.089 (3)0.035 (3)0.030 (3)
O40.115 (4)0.155 (4)0.087 (3)0.041 (3)0.062 (3)0.068 (3)
O50.132 (4)0.132 (4)0.123 (4)0.053 (3)0.050 (3)0.090 (3)
O60.075 (2)0.148 (4)0.097 (2)0.053 (2)0.0344 (19)0.038 (2)
O70.155 (5)0.202 (6)0.189 (6)0.083 (5)0.139 (5)0.112 (5)
N10.086 (3)0.080 (3)0.053 (3)0.037 (3)0.008 (2)0.018 (2)
N20.076 (3)0.084 (3)0.053 (2)0.007 (3)0.015 (2)0.032 (2)
N30.075 (2)0.148 (4)0.097 (2)0.053 (2)0.0344 (19)0.038 (2)
N110.045 (2)0.064 (2)0.0374 (18)0.0145 (17)0.0070 (15)0.0200 (16)
N210.054 (2)0.070 (2)0.0426 (19)0.0142 (19)0.0131 (16)0.0234 (18)
C10.046 (2)0.068 (3)0.033 (2)−0.002 (2)0.0032 (18)0.016 (2)
C20.054 (3)0.057 (3)0.038 (2)0.012 (2)0.0044 (19)0.0127 (19)
C30.046 (2)0.067 (3)0.036 (2)0.009 (2)0.0089 (18)0.010 (2)
C40.054 (3)0.058 (3)0.037 (2)0.002 (2)0.0094 (19)0.0171 (19)
C50.050 (3)0.061 (3)0.046 (2)0.011 (2)0.006 (2)0.017 (2)
C60.039 (2)0.070 (3)0.041 (2)0.009 (2)0.0106 (18)0.012 (2)
C110.049 (3)0.050 (2)0.039 (2)0.018 (2)0.0099 (18)0.0188 (18)
C120.064 (3)0.055 (3)0.043 (2)0.006 (2)0.002 (2)0.027 (2)
C140.161 (7)0.111 (4)0.217 (8)0.048 (4)0.005 (6)0.082 (5)
C150.161 (7)0.111 (4)0.217 (8)0.048 (4)0.005 (6)0.082 (5)
C210.047 (3)0.058 (3)0.043 (2)0.011 (2)0.0138 (19)0.021 (2)
C220.050 (3)0.063 (3)0.043 (2)0.016 (2)0.0127 (19)0.017 (2)
C230.065 (3)0.066 (3)0.072 (3)0.012 (3)−0.005 (3)0.019 (3)
C240.071 (4)0.080 (4)0.091 (4)0.010 (3)0.004 (3)−0.015 (3)
C250.081 (4)0.128 (6)0.104 (5)0.039 (4)0.024 (4)0.040 (4)
C1320.047 (4)0.093 (5)0.040 (4)0.011 (4)0.018 (3)0.033 (4)
Geometric parameters (Å, º) top
O1A—C111.236 (5)C23—H23A0.9700
O1B—C111.263 (5)C23—H23B0.9700
C11—C121.515 (6)C24—S211.51 (5)
C12—C1311.398 (15)C24—S21.71 (2)
C12—N111.482 (5)C24—S221.90 (3)
C12—C1321.697 (9)C24—H24A0.9700
C12—H22A0.9800C24—H24B0.9700
C12—H12B0.9800C24—H24C0.9699
N11—H11A0.8900C24—H24D0.9700
N11—H11B0.8900C24—H24E0.9700
N11—H11C0.8900C24—H24F0.9699
C131—C141.143 (15)S2—C251.83 (3)
C131—H13A0.9700S2—H24D1.4200
C131—H13B0.9700S21—C251.75 (5)
C132—C141.408 (11)S21—H24F1.0961
C132—H13C0.9700S21—H25H1.4301
C132—H13D0.9700S22—C251.75 (4)
C14—S11.714 (12)S22—H24D1.5898
C14—S121.818 (15)S22—H25D1.8386
C14—S111.89 (2)S22—H25F1.8131
C14—H14A0.9700C25—H25A0.9600
C14—H14B0.9700C25—H25B0.9600
C14—H14C0.9700C25—H25C0.9600
C14—H14D0.9700C25—H25D0.9600
S1—C151.478 (14)C25—H25E0.9600
S1—H15H1.6850C25—H25F0.9600
S11—C151.84 (3)C25—H25G0.9600
S12—C151.861 (17)C25—H25H0.9600
C15—H15A0.9600C25—H25I0.9600
C15—H15B0.9600O1—C11.255 (5)
C15—H15C0.9600O2—N11.225 (5)
C15—H15D0.9600O3—N11.229 (6)
C15—H15E0.9600O4—N21.217 (6)
C15—H15F0.9600O5—N21.216 (6)
C15—H15G0.9600O6—N31.197 (7)
C15—H15H0.9600O7—N31.187 (7)
C15—H15I0.9600N1—C21.448 (6)
O2A—C211.218 (5)N2—C41.455 (6)
O2B—C211.276 (5)N3—C61.449 (7)
O2B—H2B0.8200C1—C61.435 (7)
C21—C221.518 (6)C1—C21.438 (6)
C22—N211.486 (6)C2—C31.371 (6)
C22—C231.513 (7)C3—C41.363 (6)
C22—H220.9800C3—H30.9300
N21—H21A0.8900C4—C51.380 (6)
N21—H21B0.8900C5—C61.376 (6)
N21—H21C0.8900C5—H50.9300
C23—C241.537 (8)
O1A—C11—O1B125.3 (4)H21A—N21—H21C109.5
O1A—C11—C12120.1 (4)H21B—N21—H21C109.5
O1B—C11—C12114.6 (3)C22—C23—C24115.7 (5)
C131—C12—N11126.1 (7)C22—C23—H23A108.4
C131—C12—C11115.5 (7)C24—C23—H23A108.4
N11—C12—C11109.8 (3)C22—C23—H23B108.4
C131—C12—C13234.9 (7)C24—C23—H23B108.4
N11—C12—C132103.3 (4)H23A—C23—H23B107.4
C11—C12—C132109.1 (4)S21—C24—C23119.2 (19)
C131—C12—H22A99.8S21—C24—S262 (2)
N11—C12—H22A99.8C23—C24—S2117.2 (8)
C11—C12—H22A99.8S21—C24—S2263 (2)
C132—C12—H22A133.6C23—C24—S22112.8 (12)
C131—C12—H12B79.6S2—C24—S224.4 (19)
N11—C12—H12B110.5S21—C24—H24A131.0
C11—C12—H12B110.5C23—C24—H24A108.0
C132—C12—H12B113.4S2—C24—H24A108.0
H22A—C12—H12B20.3S22—C24—H24A110.7
C12—N11—H11A109.5S21—C24—H24B47.2
C12—N11—H11B109.5C23—C24—H24B108.0
H11A—N11—H11B109.5S2—C24—H24B108.0
C12—N11—H11C109.5S22—C24—H24B109.9
H11A—N11—H11C109.5H24A—C24—H24B107.2
H11B—N11—H11C109.5S21—C24—H24C104.5
C14—C131—C12166.8 (15)C23—C24—H24C105.7
C14—C131—H12B150.6S2—C24—H24C136.2
C12—C131—H12B38.3S22—C24—H24C140.6
C14—C131—H13A94.1H24A—C24—H24C46.8
C12—C131—H13A94.1H24B—C24—H24C63.5
H12B—C131—H13A94.7S21—C24—H24D115.3
C14—C131—H13B94.1C23—C24—H24D105.1
C12—C131—H13B94.1S2—C24—H24D56.1
H12B—C131—H13B56.6S22—C24—H24D56.7
H13A—C131—H13B103.1H24A—C24—H24D60.1
C14—C131—H14D45.8H24B—C24—H24D146.9
C12—C131—H14D144.5H24C—C24—H24D106.0
H12B—C131—H14D106.2S21—C24—H24E130.4
H13A—C131—H14D89.7C23—C24—H24E108.9
H13B—C131—H14D50.8S2—C24—H24E106.5
C14—C132—C12108.4 (6)S22—C24—H24E109.1
C14—C132—H13C110.0H24A—C24—H24E1.5
C12—C132—H13C110.0H24B—C24—H24E107.9
C14—C132—H13D110.0H24C—C24—H24E48.0
C12—C132—H13D110.0H24D—C24—H24E58.7
H13C—C132—H13D108.4S21—C24—H24F46.2
C131—C14—C13243.3 (9)C23—C24—H24F109.3
C131—C14—S1149.6 (13)S2—C24—H24F106.8
C132—C14—S1109.9 (9)S22—C24—H24F108.9
C131—C14—S12156.5 (14)H24A—C24—H24F107.1
C132—C14—S12113.2 (9)H24B—C24—H24F1.4
S1—C14—S1216.5 (5)H24C—C24—H24F63.8
C131—C14—S11139.0 (14)H24D—C24—H24F145.7
C132—C14—S1196.0 (10)H24E—C24—H24F107.7
S1—C14—S1126.2 (7)C24—S2—C25102.4 (12)
S12—C14—S1118.0 (5)C24—S2—H24D34.6
C131—C14—H14A99.3C25—S2—H24D135.4
C132—C14—H14A99.0C24—S21—C25115 (3)
S1—C14—H14A99.3C24—S21—H24F39.7
S12—C14—H14A82.8C25—S21—H24F148.5
S11—C14—H14A79.7C24—S21—H25H148.0
C131—C14—H14B99.3C25—S21—H25H33.2
C132—C14—H14B139.1H24F—S21—H25H160.5
S1—C14—H14B99.3C25—S22—C2498.1 (18)
S12—C14—H14B103.0C25—S22—H24D128.5
S11—C14—H14B120.9C24—S22—H24D30.7
H14A—C14—H14B104.0C25—S22—H25D30.9
C131—C14—H14C107.0C24—S22—H25D125.6
C132—C14—H14C107.2H24D—S22—H25D155.7
S1—C14—H14C93.8C25—S22—H25F31.2
S12—C14—H14C77.3C24—S22—H25F98.1
S11—C14—H14C76.6H24D—S22—H25F121.0
H14A—C14—H14C8.7H25D—S22—H25F50.8
H14B—C14—H14C98.5S21—C25—S2262.9 (19)
C131—C14—H14D76.5S21—C25—S255.8 (18)
C132—C14—H14D116.4S22—C25—S27.2 (18)
S1—C14—H14D118.3S21—C25—H25A148.3
S12—C14—H14D125.0S22—C25—H25A103.8
S11—C14—H14D142.7S2—C25—H25A109.5
H14A—C14—H14D110.8S21—C25—H25B60.1
H14B—C14—H14D23.0S22—C25—H25B116.1
H14C—C14—H14D108.2S2—C25—H25B109.5
C15—S1—C14124.8 (9)H25A—C25—H25B109.5
C15—S1—H15H34.6S21—C25—H25C102.2
C14—S1—H15H112.2S22—C25—H25C108.3
C15—S11—C1498.4 (11)S2—C25—H25C109.5
C14—S12—C15100.6 (7)H25A—C25—H25C109.5
S1—C15—S1126.3 (9)H25B—C25—H25C109.5
S1—C15—S1212.1 (6)S21—C25—H25D116.3
S11—C15—S1218.2 (6)S22—C25—H25D79.7
S1—C15—H15A109.5S2—C25—H25D83.5
S11—C15—H15A101.0H25A—C25—H25D32.7
S12—C15—H15A99.8H25B—C25—H25D101.5
S1—C15—H15B109.5H25C—C25—H25D139.2
S11—C15—H15B134.6S21—C25—H25E101.3
S12—C15—H15B120.6S22—C25—H25E164.1
H15A—C15—H15B109.5S2—C25—H25E157.0
S1—C15—H15C109.5H25A—C25—H25E90.0
S11—C15—H15C90.1H25B—C25—H25E50.4
S12—C15—H15C107.4H25C—C25—H25E73.6
H15A—C15—H15C109.5H25D—C25—H25E109.5
H15B—C15—H15C109.5S21—C25—H25F110.4
S1—C15—H15D97.3S22—C25—H25F78.1
S11—C15—H15D92.1S2—C25—H25F82.4
S12—C15—H15D88.4H25A—C25—H25F93.1
H15A—C15—H15D12.9H25B—C25—H25F148.0
H15B—C15—H15D111.0H25C—C25—H25F39.6
H15C—C15—H15D119.3H25D—C25—H25F109.5
S1—C15—H15E125.7H25E—C25—H25F109.5
S11—C15—H15E149.5S21—C25—H25G150.5
S12—C15—H15E137.1S22—C25—H25G108.8
H15A—C15—H15E104.2S2—C25—H25G114.5
H15B—C15—H15E16.8H25A—C25—H25G5.0
H15C—C15—H15E97.4H25B—C25—H25G106.6
H15D—C15—H15E109.5H25C—C25—H25G107.2
S1—C15—H15F104.2H25D—C25—H25G36.5
S11—C15—H15F81.8H25E—C25—H25G85.0
S12—C15—H15F99.8H25F—C25—H25G94.1
H15A—C15—H15F101.3S21—C25—H25H54.7
H15B—C15—H15F122.3S22—C25—H25H109.6
H15C—C15—H15F12.9S2—C25—H25H103.0
H15D—C15—H15F109.5H25A—C25—H25H111.9
H15E—C15—H15F109.5H25B—C25—H25H6.5
S1—C15—H15G118.0H25C—C25—H25H113.3
S11—C15—H15G108.6H25D—C25—H25H100.3
S12—C15—H15G108.2H25E—C25—H25H56.9
H15A—C15—H15G8.5H25F—C25—H25H150.2
H15B—C15—H15G105.3H25G—C25—H25H109.5
H15C—C15—H15G104.8S21—C25—H25I99.8
H15D—C15—H15G21.2S22—C25—H25I110.0
H15E—C15—H15G98.1S2—C25—H25I110.7
H15F—C15—H15G98.1H25A—C25—H25I112.0
S1—C15—H15H84.6H25B—C25—H25I105.7
S11—C15—H15H110.9H25C—C25—H25I3.9
S12—C15—H15H94.7H25D—C25—H25I142.4
H15A—C15—H15H109.6H25E—C25—H25I71.0
H15B—C15—H15H27.2H25F—C25—H25I43.2
H15C—C15—H15H130.4H25G—C25—H25I109.5
H15D—C15—H15H104.8H25H—C25—H25I109.5
H15E—C15—H15H43.8O2—N1—O3121.9 (5)
H15F—C15—H15H142.9O2—N1—C2119.7 (4)
H15G—C15—H15H109.5O3—N1—C2118.4 (4)
S1—C15—H15I122.1O5—N2—O4123.6 (5)
S11—C15—H15I109.0O5—N2—C4118.3 (5)
S12—C15—H15I124.1O4—N2—C4118.1 (5)
H15A—C15—H15I116.6O7—N3—O6119.2 (6)
H15B—C15—H15I86.7O7—N3—C6121.6 (6)
H15C—C15—H15I23.0O6—N3—C6119.1 (6)
H15D—C15—H15I129.0O1—C1—C6124.4 (4)
H15E—C15—H15I74.4O1—C1—C2123.0 (5)
H15F—C15—H15I35.6C6—C1—C2112.7 (4)
H15G—C15—H15I109.5C3—C2—C1123.3 (4)
H15H—C15—H15I109.5C3—C2—N1116.0 (4)
C21—O2B—H2B109.5C1—C2—N1120.7 (4)
O2A—C21—O2B126.1 (4)C4—C3—C2120.0 (4)
O2A—C21—C22121.3 (4)C4—C3—H3120.0
O2B—C21—C22112.6 (4)C2—C3—H3120.0
N21—C22—C23112.3 (4)C3—C4—C5121.4 (4)
N21—C22—C21108.4 (4)C3—C4—N2119.4 (4)
C23—C22—C21112.8 (4)C5—C4—N2119.1 (4)
N21—C22—H22107.7C6—C5—C4118.5 (4)
C23—C22—H22107.7C6—C5—H5120.7
C21—C22—H22107.7C4—C5—H5120.7
C22—N21—H21A109.5C5—C6—C1124.1 (4)
C22—N21—H21B109.5C5—C6—N3116.5 (5)
H21A—N21—H21B109.5C1—C6—N3119.5 (4)
C22—N21—H21C109.5
O1A—C11—C12—C131−136.7 (9)C22—C23—C24—S21141 (2)
O1B—C11—C12—C13143.4 (10)C22—C23—C24—S269.5 (11)
O1A—C11—C12—N1113.2 (6)C22—C23—C24—S2269.9 (15)
O1B—C11—C12—N11−166.7 (4)S21—C24—S2—C25−36 (2)
O1A—C11—C12—C132−99.4 (5)C23—C24—S2—C2574.4 (11)
O1B—C11—C12—C13280.7 (5)C23—C24—S21—C25−66 (3)
N11—C12—C131—C14−113 (7)S2—C24—S21—C2541 (2)
C11—C12—C131—C1431 (8)S22—C24—S21—C2537 (2)
C132—C12—C131—C14−56 (7)S21—C24—S22—C25−33 (2)
C131—C12—C132—C149.3 (12)C23—C24—S22—C2579.3 (16)
N11—C12—C132—C14145.1 (6)C24—S21—C25—S22−41 (3)
C11—C12—C132—C14−98.1 (7)C24—S21—C25—S2−42 (2)
C12—C131—C14—C13256 (7)C24—S22—C25—S2128 (2)
C12—C131—C14—S190 (7)C24—S22—C25—S234 (12)
C12—C131—C14—S1256 (9)C24—S2—C25—S2133 (2)
C12—C131—C14—S1148 (8)C24—S2—C25—S22−141 (14)
C12—C132—C14—C131−9.5 (12)O1—C1—C2—C3178.4 (4)
C12—C132—C14—S1−172.1 (6)C6—C1—C2—C3−1.6 (6)
C12—C132—C14—S12170.5 (7)O1—C1—C2—N1−3.9 (7)
C12—C132—C14—S11165.0 (8)C6—C1—C2—N1176.1 (4)
C131—C14—S1—C1519 (3)O2—N1—C2—C3−159.0 (5)
C132—C14—S1—C1542.8 (14)O3—N1—C2—C319.9 (7)
S12—C14—S1—C15148 (3)O2—N1—C2—C123.2 (7)
S11—C14—S1—C15104 (3)O3—N1—C2—C1−158.0 (5)
C131—C14—S11—C1589.6 (19)C1—C2—C3—C4−0.2 (7)
C132—C14—S11—C1583.8 (10)N1—C2—C3—C4−178.0 (4)
S1—C14—S11—C15−40.2 (17)C2—C3—C4—C51.7 (7)
S12—C14—S11—C15−80 (3)C2—C3—C4—N2178.3 (4)
C131—C14—S12—C1561 (3)O5—N2—C4—C3−179.3 (5)
C132—C14—S12—C1560.8 (11)O4—N2—C4—C3−1.5 (7)
S1—C14—S12—C15−21 (2)O5—N2—C4—C5−2.6 (7)
S11—C14—S12—C1579 (3)O4—N2—C4—C5175.2 (5)
C14—S1—C15—S11−97 (2)C3—C4—C5—C6−1.2 (7)
C14—S1—C15—S12−134 (4)N2—C4—C5—C6−177.8 (4)
C14—S11—C15—S148.2 (15)C4—C5—C6—C1−0.9 (7)
C14—S11—C15—S1272 (3)C4—C5—C6—N3179.2 (4)
C14—S12—C15—S134 (3)O1—C1—C6—C5−177.9 (4)
C14—S12—C15—S11−86 (3)C2—C1—C6—C52.1 (6)
O2A—C21—C22—N21−2.4 (5)O1—C1—C6—N32.1 (7)
O2B—C21—C22—N21176.6 (3)C2—C1—C6—N3−177.9 (4)
O2A—C21—C22—C23122.6 (5)O7—N3—C6—C5−169.3 (7)
O2B—C21—C22—C23−58.4 (5)O6—N3—C6—C56.8 (8)
N21—C22—C23—C24−80.0 (6)O7—N3—C6—C110.8 (9)
C21—C22—C23—C24157.2 (4)O6—N3—C6—C1−173.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2B—H2B···O1Bi0.821.662.457 (5)163
N11—H11A···O1Ai0.892.112.901 (5)147
N11—H11B···O2Aii0.892.062.868 (4)151
N11—H11C···O10.892.062.861 (5)149
N11—H11C···O20.892.262.928 (5)131
N21—H21A···O4iii0.892.573.062 (5)115
N21—H21B···O1Aii0.892.072.955 (4)174
N21—H21C···O10.891.972.820 (5)160
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC5H11NO2S·C5H12NO2S+·C6H2N3O7−
Mr527.53
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.076 (1), 12.102 (1), 14.895 (2)
α, β, γ (°)103.90 (1), 97.04 (2), 101.73 (2)
V (Å3)1192.4 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.2 × 0.15 × 0.10
Data collection
DiffractometerNonius MACH3 four-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.943, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections		4940, 4217, 2516
Rint0.014
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.237, 1.03
No. of reflections4217
No. of parameters331
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.80, −0.56

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXTL/PC (Bruker, 2000), SHELXTL/PC, PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997).

Selected geometric parameters (Å, º) top
O1A—C111.236 (5)O2A—C211.218 (5)
O1B—C111.263 (5)O2B—C211.276 (5)
O1A—C11—O1B125.3 (4)O2A—C21—O2B126.1 (4)
O1A—C11—C12120.1 (4)O2A—C21—C22121.3 (4)
O1B—C11—C12114.6 (3)O2B—C21—C22112.6 (4)
O1A—C11—C12—N1113.2 (6)C23—C24—S2—C2574.4 (11)
O1B—C11—C12—N11−166.7 (4)O3—N1—C2—C319.9 (7)
N11—C12—C132—C14145.1 (6)O2—N1—C2—C123.2 (7)
C132—C14—S1—C1542.8 (14)O4—N2—C4—C3−1.5 (7)
O2A—C21—C22—N21−2.4 (5)O5—N2—C4—C5−2.6 (7)
O2B—C21—C22—N21176.6 (3)O6—N3—C6—C56.8 (8)
N21—C22—C23—C24−80.0 (6)O7—N3—C6—C110.8 (9)
C22—C23—C24—S2269.9 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2B—H2B···O1Bi0.821.662.457 (5)163
N11—H11A···O1Ai0.892.112.901 (5)147
N11—H11B···O2Aii0.892.062.868 (4)151
N11—H11C···O10.892.062.861 (5)149
N11—H11C···O20.892.262.928 (5)131
N21—H21A···O4iii0.892.573.062 (5)115
N21—H21B···O1Aii0.892.072.955 (4)174
N21—H21C···O10.891.972.820 (5)160
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.
 

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