Dinicotinium sulfate

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Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

Dinicotinium sulfate

S. Athimoolam and R. K. Rajaram*

Department of Physics, Madurai Kamaraj University, Madurai 625 021, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C–C) = 0.008 A˚ Rfactor = 0.062 wRfactor = 0.205

Data-to-parameter ratio = 11.4

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography

In the title complex, 2C6H6NO2 +

SO4 2

, the carboxyl groups of the two nicotinium cations (AandB) are twisted from the pyridinium ring, with dihedral angles of 9.1 (5) and 7.0 (9)_, respectively. Packing involves classical O—H O and N— H O hydrogen bonds. CationsAare interlinked through an O atom of the sulfate anion, forming an infinite chain running along thebaxis and leading to cationic layers separated by a distance of 3.106 (4) A˚ . Cations Bform an inversion-related closed hydrogen-bonded loop.

Comment

Hypercholesterolemia is a relevant risk factor with regard to the development of atherosclerotic diseases. Nicotinic acid, a B vitamin, also known as niacin, is a lipid-lowering agent widely used to treat hypertriglyceridemia by the inhibition of lipolysis in adipose tissue. The nicotinic acid complex 5-methylpyrazine-2-carboxylic acid 4-oxide is a commonly used drug for hypercholesterolemia (Lorenzenet al., 2001). Coor-dination complexes of nicotinic acid with metals such as Sn possess antitumour activity greater than the well known cis -platin or doxorubicin (Gielen et al., 1992). Also, the enzyme nicotinic acid mononucleotide adenylyltransferase is essential for the synthesis of nicotinamide adenine dinucleotide in all living cells and is a potential target for antibiotics (Kimet al., 2004). Because of their pharmacological importance, nicotinic acid and related compounds are the object of extensive study. The crystal structures of nicotinic acid (Wright & King, 1953; Kutoglu & Scheringer, 1983), dinicotinic acid (Takusagawaet al., 1973), isonicotinic acid (Takusagawa & Shimada, 1976), isonicotinic acid hydrazide (Bhat et al., 1974), nicotinium tetrachlorocuprate(II) (Choi et al., 2002), 2-aminonicotinic acid (Dobson & Gerkin, 1997), 6-aminonicotinic acid hydro-chloride (Giantsidis & Turnbull, 2000), nicotinic acid hydro-chloride hydrochloride (Na¨ttinen & Rissanen, 2003), 3,5-dinitro-benzoic acid nicotinic acid (Zhu & Zheng, 2004), 2-(methyl-sulfanyl)nicotinic acid (Basavoju et al., 2005), nicotinamide (Wright & King, 1954), 1-methylnicotinamide iodide, chloride and picrate (Freeman & Bugg, 1974), and dinicotinamidium squarate (Bulut et al., 2003) have been reported previously. The crystal structure of nicotinic acid complexed with the protein leghaemoglobin (Ellis et al., 1997) and the haem– nicotinate interaction in leghaemoglobin (Patel et al., 2000) were also studied. As part of our investigations of nicotinic acid complexes with inorganic acids, nicotinic acid was treated with sulfuric acid, and the crystal structure of the resulting salt is reported here.

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The title compound, (I), contains two nicotinium cations (A andB) and a sulfate anion in the asymmetric unit (Fig. 1). The protons from the sulfuric acid are transferred to the nicotinic acid, forming two nicotinium cations. The least-squares plane through cation A makes an angle of 50.8 (1) _{with that for} cationB. CationsAandBare stacked close to thez= 0 andz =1

2planes, respectively. The C—N—C bond angle and the C—

N bond distances in both cations confirm protonation on the N atom of the aromatic rings. The pyridinium rings are essen-tially planar, with a maximum deviation of 0.007 (3) A˚ for N11 in cationAand 0.018 (4) A˚ for C23 in cationB. As found in other nicotinic acid–inorganic acid complexes, the carboxyl group is twisted from the pyridinium ring plane, with dihedral angles of 9.1 (5) and 7.0 (9)_{for cations}_A_and_B_{, respectively.} Protonation of the O atoms of the carboxyl groups is unam-biguously confirmed from the C—O bond distances and C— C—O bond angles. Deviation of the carbonyl atom O1A [0.191 (9) A˚ ] from the pyridinium plane is slightly greater than that of O1B[0.157 (9) A˚ ] in cationA. This is reversed in cation B, with O2B [0.235 (9) A˚ ] deviating further from the ring

plane than O2A [0.149 (9) A˚ ], as found in 2-aminonicotinic acid (Dobson & Gerkin, 1997) (Table 1). The SO4

2 anion shows nearly tetrahedral symmetry. The crystal is stabilized by extensive hydrogen bonding through three O atoms of the sulfate anions (Fig. 2). TheBcations are interlinked through N—H O and O—H O hydrogen bonds to the anions, forming an inversion-related closed hydrogen-bonded loop (Fig. 3). In residueA, the cations form infinite chains running along thebaxis by connecting to adjacent cations through the

organic papers

Acta Cryst.(2005). E61, o2764–o2767 Athimoolam and Rajaram _2C

[image:2.610.108.229.86.175.2]

5H6NO2+SO42

o2765

Figure 2

The packing of the molecule, viewed down thebaxis, with hydrogen bonds drawn as dashed lines.

Figure 1

[image:2.610.317.563.198.473.2] [image:2.610.50.313.452.717.2]

The asymmetric unit of the title compound, showing the atom-numbering scheme and 50% probability displacement ellipsoids.

Figure 3

[image:2.610.316.565.517.723.2]

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O1 atom of the sulfate anion, viz. N11—H11 O1 H1B— O1B(x, y + 1, z), leading to cationic layers separated by 3.106 (4) A˚ but not linked by any hydrogen bonding (Fig. 4 and Table 2).

Experimental

The title compound was crystallized from a solution of a mixture of nicotinic acid and sulfuric acid in a 2:1 stoichiometric ratio. Slow evaporation of the mixture at room temperature produced colourless block-like crystals, one of which was cut and used to collect the intensity data.

Crystal data

2C5H6NO2+SO42

Mr= 344.30

Triclinic,P1

a= 6.9663 (7) A˚

b= 8.3306 (14) A˚

c= 12.5098 (12) A˚

= 101.253 (11)

= 95.746 (8)

= 102.685 (11)

V= 686.85 (15) A˚3 Z= 2

Dx= 1.665 Mg m 3

Dm= 1.654 (8) Mg m

3 Dmmeasured by flotation using a

mixture of CCl4and CHBr3 MoKradiation

Cell parameters from 25 reflections

= 10.0–14.3

= 0.28 mm1 T= 293 (2) K Block, colourless 0.250.220.19 mm

Data collection

Nonius MACH3 four-circle diffractometer

!–2scans

Absorption correction: scan (Northet al., 1968)

Tmin= 0.898,Tmax= 0.947 3062 measured reflections 2414 independent reflections 1650 reflections withI> 2(I)

Rint= 0.020 max= 25.0

h=1!8

k=9!9

l=14!14 3 standard reflections

frequency: 60 min intensity decay: none

Refinement

Refinement onF2 R[F2_{> 2}₍_F2_{)] = 0.062} wR(F2) = 0.205

S= 1.13 2409 reflections 211 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0826P)2 + 2.2093P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.53 e A˚

3 min=0.59 e A˚

3

Table 1

Selected geometric parameters (A˚ ,_).

N11—C12 1.331 (7) N11—C16 1.342 (7) C131—O1A 1.204 (7) C131—O1B 1.311 (7)

N21—C22 1.338 (7) N21—C26 1.345 (7) C231—O2A 1.193 (6) C231—O2B 1.318 (6)

C12—N11—C16 122.9 (5) O1A—C131—O1B 124.9 (5)

C22—N21—C26 121.9 (5) O2A—C231—O2B 125.0 (5)

C14—C13—C131—O1A 9.6 (8) C14—C13—C131—O1B 171.9 (5)

C24—C23—C231—O2A 2.3 (8) C24—C23—C231—O2B 175.1 (5)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N11—H11 O1i

0.86 1.91 2.755 (6) 165 O1B—H1B O1ii

0.82 1.76 2.582 (6) 178 O2B—H2B O2 0.82 1.72 2.528 (5) 168 N21—H21 O3iii

0.86 1.80 2.641 (6) 167

Symmetry codes: (i) xþ1;yþ1;z; (ii) xþ1;y;z; (iii) xþ2;yþ1;zþ1.

Five strong reflections were omitted from the final refinement as they showedIo<<Ic. This may be due to primary extinction. All H

atoms were placed in geometrically calculated positions, with C—H = 0.93 A˚ , N—H = 0.86 A˚ and O—H = 0.82 A˚, and allowed to ride on their carrier atoms, withUiso(H) = 1.2Ueq(C) and 1.5Ueq(N,O).

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: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication:SHELXTL/PC.

The authors thank the Department of Science and Tech-nology, Government of India, for establishing a Single-Crystal Diffractometer facility at the School of Physics, Madurai Kamaraj University, Madurai, through the FIST programme.

References

Basavoju, S., Reddy, C. M. & Desiraju, G. R. (2005).Acta Cryst.E61, o822– o823.

Bhat, T. N., Singh, T. P. & Vijayan, M. (1974).Acta Cryst.B30, 2921–2922. Bruker (2000). SHELXTL/PC. Version 6.10. Bruker AXS Inc., Madison,

Wisconsin, USA.

Bulut, A., Yesilel, O. Z., Dege, N., Icbudak, H., Olmaz, H. & Bujukgungor, O. (2003).Acta Cryst.C59, o727–o729.

Choi, S. N., Lee, Y. M., Lee, H. W., Kangb, S. K. & Kim, Y. I. (2002).Acta Cryst.

E58, m583–m585.

Dobson, A. J. & Gerkin, R. E. (1997).Acta Cryst.C53, 1427–1429.

[image:3.610.315.564.70.258.2]

Ellis, P. J., Appleby, C. A., Guss, J. M., Hunter, W. N., Ollis, D. L. & Freeman, H. C. (1997).Acta Cryst.D53, 302–310.

Figure 4

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Enraf–Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf–Nonius, Delft, The Netherlands.

Freeman, G. R. & Bugg, C. E. (1974).Acta Cryst.B30, 431–443. Giantsidis, J. & Turnbull, M. M. (2000).Acta Cryst.C56, 334–335.

Gielen, M., Khloufi, A. E., Biesemans, M. & Willem, R. (1992).Polyhedron,

11, 1861–1868.

Harms, K. & Wocadlo, S. (1995).XCAD4.University of Marburg. Germany. Kim, H. L., Yoon, H. J., Ha, J. Y., Lee, B. I., Lee, H. H., Mikami, B. & Suh, W. S.

(2004).Acta Cryst.D60, 948–949.

Kutoglu, A. & Scheringer, C. (1983).Acta Cryst.C39, 232–234.

Lorenzen, A., Stannek, C., Lang, H., Andrianov, V., Kalvinsh, I. & Schwabe, U. (2001).Mol. Pharmacol.59, 349–357.

Na¨ttinen, K. I. & Rissanen, K. (2003).CrystEngComm,5, 326–330. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351–

359.

Patel, N., Jones, D. K. & Raven, E. L. (2000).Eur. J. Biochem.267, 2581–2587. Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Takusagawa, F., Hirotsu, K. & Shimada, A. (1973).Bull. Chem. Soc. Jpn,46, 2292–2299.

Takusagawa, F. & Shimada, A. (1976).Acta Cryst.B32, 1925–1927. Wright, W. B. & King, G. S. D. (1953).Acta Cryst.6, 305–310. Wright, W. B. & King, G. S. D. (1954).Acta Cryst.7, 283–288.

Zhu, J. & Zheng, J. M. (2004).Jiegou Huaxue(Chin. J. Struct. Chem.),23, 417– 420. (In Chinese.)

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sup-1 Acta Cryst. (2005). E61, o2764–o2767

supporting information

Acta Cryst. (2005). E61, o2764–o2767 [https://doi.org/10.1107/S1600536805023871]

Dinicotinium sulfate

S. Athimoolam and R. K. Rajaram

Dinicotinium sulfate

Crystal data

2C5H6NO2+·SO42−

Mr = 344.30 Triclinic, P1 a = 6.9663 (7) Å b = 8.3306 (14) Å c = 12.5098 (12) Å α = 101.253 (11)° β = 95.746 (8)° γ = 102.685 (11)° V = 686.85 (15) Å3

Z = 2 F(000) = 356

Dx = 1.665 Mg m−3

Dm = 1.654 Mg m−3

Dm measured by flotation using a mixture of

CCl4 and CHBr3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 10.0–14.3°

µ = 0.28 mm−1

T = 293 K Block, colorless 0.25 × 0.22 × 0.19 mm

Data collection

Nonius MACH3 four-circle diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω–2θ scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.898, Tmax = 0.947

3062 measured reflections

2414 independent reflections 1650 reflections with I > 2σ(I) Rint = 0.020

θmax = 25.0°, θmin = 2.6°

h = −1→8 k = −9→9 l = −14→14

3 standard reflections every 60 min intensity decay: none

Refinement

Refinement on F2

Least-squares matrix: full R[F2_{> 2}_σ₍_F2_{)] = 0.062}

wR(F2_{) = 0.205}

S = 1.13 2409 reflections 211 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2₍_F

o2) + (0.0826P)2 + 2.2093P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.53 e Å−3

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supporting information

Special details

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₎

x y z Uiso*/Ueq

N11 0.2066 (7) 0.9219 (6) −0.0206 (4) 0.0355 (11)

H11 0.1538 0.9746 −0.0634 0.043*

C12 0.1797 (8) 0.7556 (7) −0.0536 (4) 0.0322 (12)

H12 0.1026 0.6984 −0.1209 0.039*

C13 0.2665 (8) 0.6683 (7) 0.0124 (4) 0.0319 (12) C14 0.3770 (8) 0.7564 (7) 0.1119 (5) 0.0375 (13)

H14 0.4368 0.6999 0.1575 0.045*

C15 0.3997 (9) 0.9278 (8) 0.1445 (5) 0.0394 (14)

H15 0.4737 0.9870 0.2123 0.047*

C16 0.3125 (9) 1.0108 (8) 0.0766 (5) 0.0394 (14)

H16 0.3266 1.1267 0.0975 0.047*

C131 0.2393 (8) 0.4808 (7) −0.0222 (5) 0.0355 (13) O1A 0.2902 (7) 0.3992 (5) 0.0400 (4) 0.0515 (12) O1B 0.1521 (7) 0.4182 (5) −0.1244 (3) 0.0488 (11)

H1B 0.1362 0.3154 −0.1387 0.073*

N21 0.6370 (7) 0.7967 (6) 0.5124 (4) 0.0344 (11)

H21 0.7086 0.8762 0.5649 0.041*

C22 0.7216 (8) 0.6820 (7) 0.4584 (4) 0.0317 (12)

H22 0.8568 0.6907 0.4765 0.038*

C23 0.6081 (7) 0.5512 (6) 0.3762 (4) 0.0282 (11) C24 0.4074 (8) 0.5456 (7) 0.3463 (5) 0.0359 (13)

H24 0.3288 0.4603 0.2894 0.043*

C25 0.3272 (8) 0.6704 (7) 0.4034 (5) 0.0390 (14)

H25 0.1948 0.6702 0.3840 0.047*

C26 0.4430 (8) 0.7910 (7) 0.4867 (5) 0.0359 (13)

H26 0.3883 0.8712 0.5270 0.043*

C231 0.6902 (8) 0.4115 (7) 0.3203 (4) 0.0307 (12) O2A 0.5922 (6) 0.2982 (5) 0.2487 (3) 0.0463 (11) O2B 0.8761 (6) 0.4250 (5) 0.3616 (3) 0.0412 (10)

H2B 0.9085 0.3378 0.3370 0.062*

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Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

N11 0.030 (2) 0.039 (3) 0.045 (3) 0.017 (2) 0.013 (2) 0.014 (2) C12 0.024 (3) 0.039 (3) 0.036 (3) 0.014 (2) 0.010 (2) 0.004 (2) C13 0.029 (3) 0.034 (3) 0.036 (3) 0.012 (2) 0.012 (2) 0.008 (2) C14 0.036 (3) 0.044 (3) 0.037 (3) 0.015 (3) 0.007 (2) 0.014 (3) C15 0.039 (3) 0.046 (3) 0.028 (3) 0.007 (3) 0.004 (2) 0.000 (2) C16 0.036 (3) 0.039 (3) 0.045 (3) 0.014 (3) 0.017 (3) 0.001 (3) C131 0.031 (3) 0.037 (3) 0.044 (3) 0.014 (2) 0.012 (3) 0.011 (3) O1A 0.060 (3) 0.044 (2) 0.054 (3) 0.019 (2) 0.003 (2) 0.015 (2) O1B 0.065 (3) 0.032 (2) 0.046 (3) 0.012 (2) 0.001 (2) 0.0026 (19) N21 0.040 (3) 0.033 (2) 0.031 (2) 0.017 (2) 0.004 (2) 0.0017 (19) C22 0.028 (3) 0.033 (3) 0.036 (3) 0.012 (2) 0.006 (2) 0.006 (2) C23 0.027 (3) 0.030 (3) 0.030 (3) 0.010 (2) 0.008 (2) 0.008 (2) C24 0.030 (3) 0.031 (3) 0.044 (3) 0.008 (2) 0.001 (2) 0.005 (2) C25 0.022 (3) 0.036 (3) 0.065 (4) 0.017 (2) 0.009 (3) 0.014 (3) C26 0.032 (3) 0.032 (3) 0.054 (4) 0.018 (3) 0.020 (3) 0.017 (3) C231 0.031 (3) 0.029 (3) 0.035 (3) 0.011 (2) 0.007 (2) 0.005 (2) O2A 0.035 (2) 0.043 (2) 0.052 (3) 0.0152 (19) −0.001 (2) −0.012 (2) O2B 0.031 (2) 0.035 (2) 0.055 (3) 0.0176 (17) 0.0018 (19) −0.0047 (19) S1 0.0318 (7) 0.0311 (7) 0.0310 (7) 0.0176 (6) 0.0028 (5) 0.0025 (5) O1 0.042 (2) 0.041 (2) 0.038 (2) 0.0115 (18) 0.0006 (18) 0.0010 (18) O2 0.031 (2) 0.035 (2) 0.053 (2) 0.0184 (17) 0.0045 (18) 0.0025 (18) O3 0.059 (3) 0.043 (2) 0.057 (3) 0.033 (2) −0.021 (2) −0.003 (2) O4 0.053 (3) 0.063 (3) 0.061 (3) 0.022 (2) 0.034 (2) 0.023 (2)

Geometric parameters (Å, º)

N11—C12 1.331 (7) N21—H21 0.8600

N11—C16 1.342 (7) C22—C23 1.375 (7)

N11—H11 0.8600 C22—H22 0.9300

C12—C13 1.380 (8) C23—C24 1.399 (7)

C12—H12 0.9300 C23—C231 1.492 (7)

C13—C14 1.372 (8) C24—C25 1.395 (8)

C13—C131 1.501 (8) C24—H24 0.9300

C14—C15 1.375 (8) C25—C26 1.347 (8)

C14—H14 0.9300 C25—H25 0.9300

C15—C16 1.371 (8) C26—H26 0.9300

C15—H15 0.9300 C231—O2A 1.193 (6)

C16—H16 0.9300 C231—O2B 1.318 (6)

C131—O1A 1.204 (7) O2B—H2B 0.8200

C131—O1B 1.311 (7) S1—O4 1.442 (4)

O1B—H1B 0.8200 S1—O2 1.469 (4)

N21—C22 1.338 (7) S1—O3 1.471 (4)

N21—C26 1.345 (7) S1—O1 1.478 (4)

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supporting information

C12—N11—H11 118.5 N21—C22—H22 120.1

C16—N11—H11 118.5 C23—C22—H22 120.1

N11—C12—C13 119.8 (5) C22—C23—C24 119.1 (5)

N11—C12—H12 120.1 C22—C23—C231 122.1 (5)

C13—C12—H12 120.1 C24—C23—C231 118.7 (5)

C14—C13—C12 118.5 (5) C25—C24—C23 118.8 (5)

C14—C13—C131 120.3 (5) C25—C24—H24 120.6

C12—C13—C131 121.2 (5) C23—C24—H24 120.6

C13—C14—C15 120.4 (5) C26—C25—C24 119.5 (5)

C13—C14—H14 119.8 C26—C25—H25 120.2

C15—C14—H14 119.8 C24—C25—H25 120.2

C16—C15—C14 119.6 (5) N21—C26—C25 120.7 (5)

C16—C15—H15 120.2 N21—C26—H26 119.6

C14—C15—H15 120.2 C25—C26—H26 119.6

N11—C16—C15 118.8 (5) O2A—C231—O2B 125.0 (5)

N11—C16—H16 120.6 O2A—C231—C23 122.2 (5)

C15—C16—H16 120.6 O2B—C231—C23 112.7 (4)

O1A—C131—O1B 124.9 (5) C231—O2B—H2B 109.5

O1A—C131—C13 122.1 (5) O4—S1—O2 110.7 (3)

O1B—C131—C13 113.0 (5) O4—S1—O3 112.0 (3)

C131—O1B—H1B 109.5 O2—S1—O3 108.8 (2)

C22—N21—C26 121.9 (5) O4—S1—O1 109.7 (3)

C22—N21—H21 119.1 O2—S1—O1 106.9 (2)

C26—N21—H21 119.1 O3—S1—O1 108.6 (2)

C16—N11—C12—C13 −1.5 (8) C26—N21—C22—C23 −1.8 (8) N11—C12—C13—C14 0.9 (8) N21—C22—C23—C24 3.4 (8) N11—C12—C13—C131 −180.0 (5) N21—C22—C23—C231 −174.4 (5) C12—C13—C14—C15 0.1 (8) C22—C23—C24—C25 −2.0 (8) C131—C13—C14—C15 −179.1 (5) C231—C23—C24—C25 176.0 (5) C13—C14—C15—C16 −0.5 (9) C23—C24—C25—C26 −1.1 (9) C12—N11—C16—C15 1.0 (8) C22—N21—C26—C25 −1.5 (8) C14—C15—C16—N11 0.0 (8) C24—C25—C26—N21 2.9 (9) C14—C13—C131—O1A 9.6 (8) C22—C23—C231—O2A −179.8 (6) C12—C13—C131—O1A −169.5 (5) C24—C23—C231—O2A 2.3 (8) C14—C13—C131—O1B −171.9 (5) C22—C23—C231—O2B 2.8 (8) C12—C13—C131—O1B 9.0 (7) C24—C23—C231—O2B −175.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N11—H11···O1i _0.86 _1.91 _{2.755 (6)} ₁₆₅

O1B—H1B···O1ii _0.82 _1.76 _{2.582 (6)} ₁₇₈

O2B—H2B···O2 0.82 1.72 2.528 (5) 168

N21—H21···O3iii _0.86 _1.80 _{2.641 (6)} ₁₆₇