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The structures of the anhydrous proton-transfer compounds of the sulfa drug sulfamethazine with 5-nitro­salicylic acid and picric acid, namely 2-(4-amino­benzene­sulfonamido)-4,6-di­methyl­pyrimidinium 2-hy­droxy-5-nitro­benzoate, C12H15N4O2S+·C7H4NO4, (I), and 2-(4-amino­benzene­sulfonamido)-4,6-di­methyl­pyrimidinium 2,4,6-tri­nitro­phenolate, C12H15N4O2S+·C6H2N3O7, (II), respectively, have been determined. In the asymmetric unit of (I), there are two independent but conformationally similar cation–anion heterodimer pairs which are formed through duplex inter­molecular N+—H...Ocarboxylate and N—H...Ocarboxylate hydrogen-bond pairs, giving a cyclic motif [graph set R22(8)]. These heterodimers form separate and different non-associated substructures through aniline N—H...O hydrogen bonds, one one-dimensional, involving carboxyl­ate O-atom acceptors, the other two-dimensional, involving both carboxyl­ate and hydroxy O-atom acceptors. The overall two-dimensional structure is stabilized by π–π inter­actions between the pyrimidinium ring and the 5-nitro­salicylate ring in both heterodimers [minimum ring-centroid separation = 3.4580 (8) Å]. For picrate (II), the cation–anion inter­action involves a slightly asymmetric chelating N—H...O R21(6) hydrogen-bonding association with the phenolate O atom, together with peripheral conjoint R12(6) inter­actions between the same N—H groups and O atoms of the ortho-related nitro groups. An inter-unit amine N—H...Osulfone hydrogen bond gives one-dimensional chains which extend along a and inter-associate through π–π inter­actions between the pyrimidinium rings [centroid–centroid separation = 3.4752 (9) Å]. The two structures reported here now bring to a total of four the crystallographically characterized examples of proton-transfer salts of sulfa­meth­azine with strong organic acids.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113009487/ky3031sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113009487/ky3031Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113009487/ky3031IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113009487/ky3031Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113009487/ky3031IIsup5.cml
Supplementary material

CCDC references: 950371; 950372

Comment top

The drug sulfamethazine [or sulfadimidine; systematic name: 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide] (O'Neil, 2001) has been used as a model for cocrystal formation (Caira, 2007; Ghosh et al., 2011), commonly forming 1:1 adducts with carboxylic acids, predominantly the benzoic acid analogues. The structures of a significant number of these have been reported, e.g. with benzoic acid (Arman et al., 2010), salicylic acid (Patel et al., 1988), anthranilic and 4-aminobenzoic acids (Caira, 1991), 4-aminosalicylic and acetylsalicylic acids (Caira, 1992), 2-nitrobenzoic acid (Smith & Wermuth, 2013a), 4-nitrobenzoic acid (Smith & Wermuth, 2012), 2,4-dinitrobenzoic and indole-2-carboxylic acids (Lynch et al., 2000), 4-chlorobenzoic acid (Lucaciu et al., 2008), and 4-hydroxybenzoic, 2,4-dihydroxybenzoic, 3,4-dichlorobenzoic, 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acids (Ghosh et al., 2011). Only two aliphatic examples are known, viz. with fumaric and sorbic acids. The structures of the cocrystals with the amides benzamide, 4-hydroxybenzamide and picolinamide (Ghosh et al., 2011) are also known. The structures of the adducts with trimethoprim, viz. a 1:1 methanol monosolvate (Bettinetti & Sardone, 1997) and a 2:1 monohydrate (Sardone et al., 1997), represent a small number of solvated examples.

In the previously mentioned cocrystals of sulfamethazine, heterodimers are usually formed through a cyclic hydrogen-bonding motif [graph set R22(8); Etter et al., 1990], involving amide N—H···Ocarboxylate and carboxylic acid O—H···Npyrimidine pairs. Other structures not involving carboxylic acids are the 1:1 complex with saccharin (Lu et al., 2008), where a protonated sulfamethazine cation is present, and the 2:1 complex with theophylline (Lu et al., 2011), in which two tautomeric forms of sulfamethazine are found: the amidine and the imidine forms, similar to those found in the benzamide cocrystal (Ghosh et al., 2011). The structures of the parent compound sulfamethazine (Tiwari et al., 1984) and its methanol monosolvate (Rambaud et al., 1985) are also known.

However, no examples of proton-transfer salts of sulfamethzine with strong `conventional' organic acids were present in the crystallographic literature before that of the structure of the anhydrous picrate salt with 3,5-dinitrosalicylic acid (DNSA) (Smith & Wermuth, 2013b). In this salt, a hydrogen-bonded heterodimer analogous to those in the non-proton-transfer cocrystals is present, the subtle variation being that, with proton transfer, one N+—H···Ocarboxylate and one N—H···Ocarboxylate interaction are involved in the R22(8) motif. The phenolate group is only involved in the intramolecular cyclic carboxylic acid O—H···O hydrogen bond, similar to that found in the majority of the proton-transfer salts of DNSA (Smith et al., 2007). We therefore carried out the reaction of sulfamethazine with other strong organic acids under similar conditions to those used in the DNSA preparation (1:1 stoichiomety in 50% ethanol–water). Suitable crystalline products were obtained with 5-nitrosalicylic acid (5-NSA) and picric acid, the title salts 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2-hydroxy-5-nitrobenzoate, (I) (Fig. 1), and 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate, (II) (Fig. 2), and the structures are reported herein. Although not as effective as picric acid for producing crystalline proton-transfer salts with amines, 5-NSA (pKa ~2.2) has proved relatively useful in this respect, particularly with the aromatic amines (Smith et al., 1996, 2005, 2006; Kumar et al., 2003).

In the 5-NSA salt of sulfamethazine, (I), the asymmetric unit (Fig. 1) contains two independent cation–anion pairs (cations labelled A and B, and anions labelled C and D, respectively), which interact through N—H···Ocarboxylate hydrogen-bonding pairs (Table 1), giving cyclic R22(8) heterodimers (AD and BC). These differ from the heterodimer adduct only in the presence in (I) of the transferred H atom on the pyrimidine N atom of the sulfamethazine cation. Asymmetry is found in the N+—H···O [2.5847 (17) Å (A) and 2.6162 (18) Å (B)] and N—H···O distances [2.7810 (18) Å (A) and 2.7221 (18) Å (B)] within the cyclic association. This asymmetry is comparable with that found in the cocrystal examples [O—H···N and N—H···O ranges for eight examples (Lynch et al., 2000) are 2.526 (4)–2.724 (4) and 2.719 (4)–2.840 (4) Å, respectively]. The corresponding values in the DNSA proton-transfer salt (Smith & Wermuth, 2013b) are 2.617 (4) and 2.729 (4) Å.

In (I), the cyclic motifs result in near-coplanarity of the pyrimidinium and 5-NSA ring systems, with inter-ring dihedral angles of 3.74 (7) and 7.84 (7)° for dimers AD and BC, respectively. [Please check amended text] The heterodimers form separate and different non-associated substructures through aniline N—H···O hydrogen bonds (Table 1), the first system being one-dimensional (AD), involving carboxylate O-atom acceptors (O11D) and extending parallel to [010] (Fig. 3a). The second system (BC) is two-dimensional, involving both carboxylate and salicylate O-atom acceptors (O12B and O2C, respectively), and extends parallel to the (011) plane (Fig. 3b). The composite structure of (I) is two-dimensional (Fig. 3c), lying in the (101) plane. Unlike the structure of the sulfamethazine salt with 3,5-dinitrosalicylic acid, no intermolecular aniline N—H···Osulfone hydrogen-bonding interactions are present. However, ππ interactions are present between the pyrimidine rings of both cations and both anions [A···.C and B···D; ring-centroid separations (Cg···Cg) = 3.4580 (8) and 3.6815 (9) Å, respectively].

For picrate salt (II) (Fig. 2), the pyrimidine ring of the sulfamethazine molecule (A) is protonated at N1A and this group, together with the adjacent amide N2A—H group, gives a slighly asymmetric chelating hydrogen-bonding association with the picrate anion through a cyclic R21(6) motif. Conjoint lateral R12(6) cyclic associations are also formed between the N1A—H donor group and the O-atom acceptors of adjacent ortho-related picrate nitro groups (Table 2). A single intermolecular amine N41AH···Osulfone hydrogen-bonding interaction between the cation–anion units gives one-dimensional chains which extend along the a cell direction (Fig. 4). Also present in the structure are ππ interactions between the pyrimidine rings of centosymmetrically related sulfamethazine cations [Cg··· Cgii = 3.4752 (9) Å; symmetry code: (ii) -x+2, -y+1, -z+1] (Fig. 5). As found in the two structures reported here and in many of the sulfamethazine adduct structures, the 4-amino ring-substituent group is often only weakly or partially involved in hydrogen-bonding associations in the crystal structures. The nitro groups of the picrate anion are variously rotated out of the plane of the benzene ring [torsion angles C1—C2—N2—O22, C3—C4—N4—O42 and C5—C6—N6—O62 of -137.67 (15), 170.19 (15) and 146.91 (16)°, respectively].

In the sulfamethazine cations, the conformation differs significantly between carboxylate (I) and picrate (II). For (I), the dihedral angles between the pyrimidinium and benzene rings of the sulfamethazine cations are 70.60 (7) (A) and 84.78 (7)° (B), compared with 78.77 (8) and 82.33 (9)° for those in the two independent heterodimers in the 4-nitrobenzoic acid adduct (Smith & Wermuth, 2012). The value for the equivalent pyrimidinium–benzene dihedral angle in the cation of (II) [58.18 (7)°] is similar to that in the picrate salt with DNSA [59.70 (17)°], but is significantly smaller than commonly found in the other adduct structures and in (I), and probably in the case of (II) is attributable to the markedly different hydrogen-bonding pattern present in that structure. In (I), the two interacting pyrimidine–5-NSA dimers are essentially planar, with inter-ring dihedral angles of 3.74 (7) and 7.84 (7)°, compared with 12.2 (2)° in the structure of the DNSA salt (Smith & Wermuth, 2013b).

The two structures presented here now give a small total of four crystallographically characterized examples of proton-transfer salts of sulfamethazine with strong organic acids.

Related literature top

For related literature, see: Arman et al. (2010); Bettinetti & Sardone (1997); Caira (1991, 1992, 2007); Etter et al. (1990); Ghosh et al. (2011); Kumar et al. (2003); Lu et al. (2008, 2011); Lucaciu et al. (2008); Lynch et al. (2000); O'Neil (2001); Patel et al. (1988); Rambaud et al. (1985); Sardone et al. (1997); Smith & Wermuth (2012, 2013a, 2013b); Smith et al. (1996, 2005, 2006, 2007); Spek (2009); Tiwari et al. (1984).

Experimental top

The title salts, (I) and (II), were prepared by the reaction of 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine; 1 mmol, 280 mg) with, respectively, 5-nitrosalicylic acid (1 mmol, 180 mg) or picric acid (1 mmol, 230 mg) in 50% ethanol–water (50 ml) under reflux for 10 min. Partial evaporation of the solvent gave colourless plates of (I) (m.p. 478–479 K) or yellow blocks of (II) (m.p. 469–471 K), from which specimens were cleaved for the X-ray analyses.

Refinement top

H atoms potentially involved in hydrogen-bonding interactions were located by difference methods, and their positional and isotropic displacement parameters were refined. In (I), the N1A—H1A distance was restrained to 0.88 (2) Å. All other H atoms were included at calculated positions [aromatic C—H = 0.95 Å or methyl C—H = 0.98 Å] and treated as riding, with Uiso(H) = 1.2Ueq(C) for aromatic or 1.5Ueq(C) for methyl H atoms. With (I), in the absence of any indication of twinning [`no twin law detected', TwinRotMat (PLATON, Spek, 2009)], the pseudo-orthorhombic P21/n unit cell was accepted. For (II), the H atoms of one of the methyl groups (C42A) were rotationally disordered over six half-sites and were treated accordingly in the refinement [Final site occupancies?].

Computing details top

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular conformation and atom-numbering scheme for the two independent hydrogen-bonded heteromolecular pairs (AD and BC) in the asymmetric unit of (I), with inter-species hydrogen bonds shown as a dashed lines. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. The molecular conformation and atom-numbering scheme for (II), with inter-species hydrogen bonds shown as a dashed lines. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 3] Fig. 3. (a) The one-dimensional hydrogen-bonded chain structure formed by the AD homodimer units in (I), extending down b. Hydrogen-bonding associations are shown as dashed lines and non-associative H atoms have been omitted. (b) The two-dimensional hydrogen-bonded structure formed by the BC homodimer units in (I). (c) The composite two-dimensional hydrogen-bonded structure of (I), viewed down a.
[Figure 4] Fig. 4. A perspective view of the two-dimensional chain structure of (II), which extends along a, showing the hydrogen-bonding associations as dashed lines.
[Figure 5] Fig. 5. A view of (II) down the a axis of the unit cell, showing the ππ stacking of the centrosymmetrically related pyrimidinium rings of the sulfamethazine cations. Hydrogen bonds are shown as dashed lines.
(I) 2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2-hydroxy-5-nitrobenzoate top
Crystal data top
C12H15N4O2S+·C7H4NO5F(000) = 1920
Mr = 461.46Dx = 1.493 Mg m3
Monoclinic, P21/nMelting point = 478–479 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 13.1611 (2) ÅCell parameters from 13808 reflections
b = 14.0977 (2) Åθ = 3.2–28.7°
c = 22.1219 (3) ŵ = 0.21 mm1
β = 90.094 (2)°T = 200 K
V = 4104.52 (10) Å3Plate, colourless
Z = 80.35 × 0.35 × 0.15 mm
Data collection top
Oxford Gemini-S Ultra CCD area-detector
diffractometer
8057 independent reflections
Radiation source: Enhance (Mo) X-ray source5991 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
h = 1616
Tmin = 0.960, Tmax = 0.980k = 1717
30179 measured reflectionsl = 2727
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0571P)2]
where P = (Fo2 + 2Fc2)/3
8057 reflections(Δ/σ)max = 0.007
621 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = 0.30 e Å3
Crystal data top
C12H15N4O2S+·C7H4NO5V = 4104.52 (10) Å3
Mr = 461.46Z = 8
Monoclinic, P21/nMo Kα radiation
a = 13.1611 (2) ŵ = 0.21 mm1
b = 14.0977 (2) ÅT = 200 K
c = 22.1219 (3) Å0.35 × 0.35 × 0.15 mm
β = 90.094 (2)°
Data collection top
Oxford Gemini-S Ultra CCD area-detector
diffractometer
8057 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
5991 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.980Rint = 0.025
30179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0351 restraint
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.28 e Å3
8057 reflectionsΔρmin = 0.30 e Å3
621 parameters
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

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*/Ueq
S1A0.07153 (3)0.67064 (3)0.69347 (2)0.0288 (1)
O11A0.02458 (8)0.62533 (8)0.70202 (5)0.0372 (4)
O12A0.08020 (9)0.77122 (8)0.70003 (5)0.0387 (4)
N1A0.12334 (9)0.56980 (9)0.53296 (6)0.0223 (4)
N2A0.10773 (10)0.65526 (10)0.62149 (6)0.0268 (4)
N3A0.10208 (9)0.49098 (9)0.62605 (6)0.0261 (4)
N41A0.37418 (14)0.48612 (14)0.85115 (8)0.0476 (7)
C2A0.11060 (11)0.56942 (10)0.59352 (7)0.0219 (4)
C4A0.10701 (11)0.40782 (10)0.59619 (7)0.0269 (5)
C5A0.11914 (11)0.40380 (11)0.53373 (7)0.0265 (5)
C6A0.12785 (10)0.48715 (10)0.50191 (7)0.0231 (4)
C11A0.16171 (12)0.61476 (11)0.73886 (7)0.0273 (5)
C21A0.25203 (13)0.66125 (11)0.75263 (7)0.0301 (5)
C31A0.32363 (13)0.61707 (12)0.78855 (7)0.0320 (5)
C41A0.30519 (13)0.52674 (11)0.81264 (7)0.0315 (5)
C42A0.09958 (15)0.32077 (12)0.63395 (8)0.0409 (6)
C51A0.21385 (13)0.48115 (11)0.79852 (7)0.0331 (6)
C61A0.14306 (12)0.52406 (11)0.76199 (7)0.0295 (5)
C62A0.14456 (12)0.49267 (11)0.43539 (7)0.0293 (5)
S1B0.92340 (3)0.25241 (3)0.79543 (2)0.0281 (1)
O11B1.01786 (8)0.29519 (8)0.77910 (5)0.0375 (4)
O12B0.91201 (9)0.15187 (8)0.78933 (5)0.0381 (4)
N1B0.87859 (9)0.35527 (10)0.95621 (6)0.0241 (4)
N2B0.90467 (10)0.26742 (10)0.86958 (6)0.0283 (4)
N3B0.91195 (10)0.43170 (9)0.86353 (6)0.0266 (4)
N41B0.58517 (14)0.44107 (13)0.66992 (9)0.0504 (7)
C2B0.89904 (11)0.35379 (10)0.89624 (7)0.0233 (5)
C4B0.90126 (11)0.51537 (11)0.89198 (7)0.0270 (5)
C5B0.88147 (12)0.52088 (11)0.95369 (7)0.0286 (5)
C6B0.86996 (11)0.43832 (11)0.98618 (7)0.0251 (5)
C11B0.82365 (11)0.31070 (11)0.75987 (7)0.0245 (5)
C21B0.72877 (12)0.26729 (11)0.75756 (7)0.0283 (5)
C31B0.65008 (12)0.31123 (11)0.72858 (7)0.0299 (5)
C41B0.66316 (12)0.39982 (11)0.70119 (7)0.0299 (5)
C42B0.91208 (14)0.60161 (11)0.85326 (8)0.0369 (6)
C51B0.75855 (12)0.44401 (11)0.70520 (7)0.0299 (5)
C61B0.83785 (12)0.39970 (11)0.73375 (7)0.0272 (5)
C62B0.84715 (13)0.43421 (12)1.05216 (8)0.0346 (6)
O2C0.86063 (10)0.12638 (9)1.12344 (6)0.0409 (4)
O11C0.87460 (9)0.10804 (8)0.93667 (5)0.0349 (4)
O12C0.86850 (10)0.19851 (8)1.01921 (5)0.0407 (4)
O51C0.88240 (11)0.29921 (9)1.05247 (7)0.0568 (5)
O52C0.88819 (14)0.23713 (10)0.96357 (7)0.0721 (7)
N5C0.88198 (11)0.23014 (10)1.01871 (8)0.0408 (6)
C1C0.87128 (11)0.03235 (11)1.03253 (7)0.0249 (5)
C2C0.86472 (11)0.04133 (11)1.09589 (7)0.0273 (5)
C3C0.86229 (12)0.03944 (12)1.13268 (8)0.0330 (5)
C4C0.86768 (12)0.12790 (12)1.10761 (8)0.0321 (5)
C5C0.87478 (11)0.13593 (11)1.04502 (8)0.0285 (5)
C6C0.87714 (11)0.05767 (11)1.00755 (7)0.0271 (5)
C11C0.87166 (11)0.11811 (11)0.99236 (7)0.0274 (5)
O2D0.14667 (11)0.79122 (9)0.36510 (6)0.0483 (5)
O11D0.11640 (9)0.81801 (8)0.55065 (5)0.0357 (4)
O12D0.13518 (10)0.72445 (8)0.47061 (5)0.0425 (4)
O51D0.12968 (12)1.22050 (9)0.42635 (7)0.0572 (5)
O52D0.11007 (10)1.16310 (8)0.51618 (6)0.0442 (5)
N5D0.12073 (10)1.15325 (10)0.46110 (7)0.0348 (5)
C1D0.12832 (11)0.88941 (11)0.45319 (7)0.0246 (5)
C2D0.13815 (12)0.87685 (11)0.39024 (7)0.0293 (5)
C3D0.14014 (13)0.95564 (12)0.35148 (8)0.0358 (6)
C4D0.13393 (12)1.04569 (12)0.37452 (8)0.0322 (5)
C5D0.12471 (11)1.05756 (11)0.43673 (7)0.0261 (5)
C6D0.12100 (11)0.98103 (10)0.47596 (7)0.0248 (5)
C11D0.12604 (12)0.80620 (11)0.49551 (7)0.0272 (5)
H1A0.1296 (15)0.6270 (12)0.5115 (9)0.066 (7)*
H2A0.1125 (14)0.7051 (14)0.6004 (9)0.050 (6)*
H5A0.121400.344400.513400.0320*
H21A0.264400.723200.737400.0360*
H31A0.386100.648200.797000.0380*
H41A0.3718 (17)0.4292 (18)0.8578 (11)0.076 (9)*
H42A0.4348 (18)0.5140 (15)0.8518 (10)0.066 (7)*
H43A0.109300.264700.608400.0610*
H44A0.032400.318000.652900.0610*
H45A0.152100.322300.665400.0610*
H51A0.200600.419800.814400.0400*
H61A0.081500.492200.752400.0350*
H63A0.215000.511200.427400.0440*
H64A0.098400.539900.417900.0440*
H65A0.131200.430600.417100.0440*
H1B0.8742 (14)0.2998 (14)0.9766 (9)0.050 (6)*
H2B0.8939 (13)0.2133 (13)0.8892 (9)0.041 (5)*
H5B0.876000.580800.973100.0340*
H21B0.718700.207200.776100.0340*
H31B0.585500.281200.727000.0360*
H41B0.5276 (18)0.4084 (16)0.6715 (11)0.076 (8)*
H42B0.5908 (15)0.4978 (15)0.6598 (9)0.052 (6)*
H43B0.866000.596800.818500.0550*
H44B0.982300.606400.838900.0550*
H45B0.895000.658200.876900.0550*
H51B0.768200.505100.688000.0360*
H61B0.902500.429600.735800.0330*
H63B0.855500.497401.069900.0520*
H64B0.893900.389801.071900.0520*
H65B0.777000.412701.058100.0520*
H2C0.8596 (18)0.1687 (18)1.0934 (12)0.088 (9)*
H3C0.856900.032701.175300.0400*
H4C0.866600.182901.132400.0380*
H6C0.882700.065400.965000.0320*
H2D0.1502 (17)0.7500 (15)0.3961 (11)0.069 (7)*
H3D0.145800.946500.309100.0430*
H4D0.135901.099200.348400.0390*
H6D0.113500.991100.518200.0300*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0366 (2)0.0253 (2)0.0246 (2)0.0057 (2)0.0043 (2)0.0012 (2)
O11A0.0326 (6)0.0433 (7)0.0358 (7)0.0063 (5)0.0071 (5)0.0024 (6)
O12A0.0566 (8)0.0255 (6)0.0340 (7)0.0101 (5)0.0032 (6)0.0046 (5)
N1A0.0231 (7)0.0198 (7)0.0239 (7)0.0007 (5)0.0004 (5)0.0017 (6)
N2A0.0393 (8)0.0188 (7)0.0222 (7)0.0012 (6)0.0028 (6)0.0017 (6)
N3A0.0305 (7)0.0219 (7)0.0258 (7)0.0005 (5)0.0009 (6)0.0015 (6)
N41A0.0518 (11)0.0364 (11)0.0544 (12)0.0002 (9)0.0185 (9)0.0039 (8)
C2A0.0210 (7)0.0223 (8)0.0225 (8)0.0016 (6)0.0000 (6)0.0016 (6)
C4A0.0271 (8)0.0218 (8)0.0318 (9)0.0009 (6)0.0002 (7)0.0009 (7)
C5A0.0279 (8)0.0195 (8)0.0322 (9)0.0002 (6)0.0006 (7)0.0047 (7)
C6A0.0192 (7)0.0243 (8)0.0257 (8)0.0014 (6)0.0023 (6)0.0016 (7)
C11A0.0359 (9)0.0255 (9)0.0204 (8)0.0006 (7)0.0038 (7)0.0027 (7)
C21A0.0445 (10)0.0230 (8)0.0227 (8)0.0031 (7)0.0033 (7)0.0025 (7)
C31A0.0370 (9)0.0297 (9)0.0293 (9)0.0040 (7)0.0007 (7)0.0073 (7)
C41A0.0412 (10)0.0273 (9)0.0259 (9)0.0047 (7)0.0015 (7)0.0054 (7)
C42A0.0611 (12)0.0245 (9)0.0370 (10)0.0028 (8)0.0039 (9)0.0050 (8)
C51A0.0459 (10)0.0230 (9)0.0304 (10)0.0024 (7)0.0004 (8)0.0026 (7)
C61A0.0353 (9)0.0266 (9)0.0265 (9)0.0050 (7)0.0022 (7)0.0009 (7)
C62A0.0324 (9)0.0300 (9)0.0255 (9)0.0030 (7)0.0019 (7)0.0026 (7)
S1B0.0368 (2)0.0250 (2)0.0224 (2)0.0059 (2)0.0015 (2)0.0006 (2)
O11B0.0336 (6)0.0452 (7)0.0338 (7)0.0075 (5)0.0063 (5)0.0026 (6)
O12B0.0594 (8)0.0246 (6)0.0304 (7)0.0115 (5)0.0033 (6)0.0038 (5)
N1B0.0285 (7)0.0221 (7)0.0218 (7)0.0000 (5)0.0007 (5)0.0017 (6)
N2B0.0444 (8)0.0196 (7)0.0209 (7)0.0023 (6)0.0004 (6)0.0021 (6)
N3B0.0318 (7)0.0234 (7)0.0247 (7)0.0012 (5)0.0000 (6)0.0013 (6)
N41B0.0495 (11)0.0296 (10)0.0719 (13)0.0001 (8)0.0258 (9)0.0056 (9)
C2B0.0251 (8)0.0232 (8)0.0215 (8)0.0013 (6)0.0016 (6)0.0013 (6)
C4B0.0270 (8)0.0239 (9)0.0302 (9)0.0001 (6)0.0010 (7)0.0023 (7)
C5B0.0335 (9)0.0245 (9)0.0278 (9)0.0005 (7)0.0016 (7)0.0040 (7)
C6B0.0228 (8)0.0272 (9)0.0252 (9)0.0010 (6)0.0011 (6)0.0016 (7)
C11B0.0330 (9)0.0236 (8)0.0168 (8)0.0008 (6)0.0013 (6)0.0018 (6)
C21B0.0412 (10)0.0213 (8)0.0224 (8)0.0014 (7)0.0038 (7)0.0004 (7)
C31B0.0322 (9)0.0254 (9)0.0322 (9)0.0033 (7)0.0001 (7)0.0048 (7)
C41B0.0374 (9)0.0250 (9)0.0274 (9)0.0033 (7)0.0054 (7)0.0043 (7)
C42B0.0520 (11)0.0261 (9)0.0327 (10)0.0004 (8)0.0047 (8)0.0043 (8)
C51B0.0443 (10)0.0217 (8)0.0236 (9)0.0025 (7)0.0012 (7)0.0027 (7)
C61B0.0325 (9)0.0260 (9)0.0232 (8)0.0030 (7)0.0018 (7)0.0001 (7)
C62B0.0421 (10)0.0339 (10)0.0279 (9)0.0030 (8)0.0045 (8)0.0037 (8)
O2C0.0644 (9)0.0274 (7)0.0310 (7)0.0040 (6)0.0002 (6)0.0009 (6)
O11C0.0451 (7)0.0326 (7)0.0269 (7)0.0026 (5)0.0013 (5)0.0059 (5)
O12C0.0668 (9)0.0249 (7)0.0304 (7)0.0046 (6)0.0010 (6)0.0051 (5)
O51C0.0772 (10)0.0245 (7)0.0686 (10)0.0024 (6)0.0139 (8)0.0057 (7)
O52C0.1214 (15)0.0410 (9)0.0538 (10)0.0047 (8)0.0094 (10)0.0133 (8)
N5C0.0386 (9)0.0293 (9)0.0545 (11)0.0021 (7)0.0038 (7)0.0036 (8)
C1C0.0192 (7)0.0252 (8)0.0303 (9)0.0020 (6)0.0025 (6)0.0049 (7)
C2C0.0273 (8)0.0243 (9)0.0303 (9)0.0034 (7)0.0013 (7)0.0002 (7)
C3C0.0374 (9)0.0339 (10)0.0277 (9)0.0038 (8)0.0007 (7)0.0058 (8)
C4C0.0267 (9)0.0280 (9)0.0415 (10)0.0022 (7)0.0015 (7)0.0101 (8)
C5C0.0203 (8)0.0248 (9)0.0404 (10)0.0005 (6)0.0012 (7)0.0011 (7)
C6C0.0210 (8)0.0312 (9)0.0290 (9)0.0002 (6)0.0004 (6)0.0013 (7)
C11C0.0239 (8)0.0279 (9)0.0303 (9)0.0033 (7)0.0020 (7)0.0051 (7)
O2D0.0902 (11)0.0265 (7)0.0283 (7)0.0028 (7)0.0147 (7)0.0059 (6)
O11D0.0570 (8)0.0265 (6)0.0235 (6)0.0013 (5)0.0009 (5)0.0034 (5)
O12D0.0757 (9)0.0197 (6)0.0320 (7)0.0045 (6)0.0147 (6)0.0019 (5)
O51D0.0918 (11)0.0228 (7)0.0570 (9)0.0029 (7)0.0057 (8)0.0089 (7)
O52D0.0656 (9)0.0297 (7)0.0373 (8)0.0035 (6)0.0029 (6)0.0090 (6)
N5D0.0378 (8)0.0219 (8)0.0448 (10)0.0005 (6)0.0030 (7)0.0012 (7)
C1D0.0268 (8)0.0224 (8)0.0246 (8)0.0019 (6)0.0023 (6)0.0013 (7)
C2D0.0374 (9)0.0232 (9)0.0272 (9)0.0029 (7)0.0065 (7)0.0016 (7)
C3D0.0490 (11)0.0353 (10)0.0230 (9)0.0057 (8)0.0060 (8)0.0024 (7)
C4D0.0377 (9)0.0270 (9)0.0318 (10)0.0042 (7)0.0011 (7)0.0084 (7)
C5D0.0261 (8)0.0211 (8)0.0311 (9)0.0018 (6)0.0009 (7)0.0011 (7)
C6D0.0260 (8)0.0253 (8)0.0232 (8)0.0000 (6)0.0013 (6)0.0008 (7)
C11D0.0302 (9)0.0237 (9)0.0278 (9)0.0009 (7)0.0032 (7)0.0019 (7)
Geometric parameters (Å, º) top
S1A—O11A1.4299 (11)C5A—H5A0.9500
S1A—O12A1.4299 (12)C21A—H21A0.9500
S1A—N2A1.6770 (14)C31A—H31A0.9500
S1A—C11A1.7417 (16)C42A—H45A0.9800
S1B—O11B1.4287 (11)C42A—H43A0.9800
S1B—O12B1.4316 (12)C42A—H44A0.9800
S1B—N2B1.6726 (14)C51A—H51A0.9500
S1B—C11B1.7362 (15)C61A—H61A0.9500
O2C—C2C1.346 (2)C62A—H65A0.9800
O11C—C11C1.2408 (19)C62A—H63A0.9800
O12C—C11C1.2804 (19)C62A—H64A0.9800
O51C—N5C1.227 (2)C4B—C5B1.392 (2)
O52C—N5C1.227 (2)C4B—C42B1.494 (2)
O2C—H2C0.89 (3)C5B—C6B1.376 (2)
O2D—C2D1.334 (2)C6B—C62B1.492 (2)
O11D—C11D1.2378 (19)C11B—C21B1.392 (2)
O12D—C11D1.2831 (19)C11B—C61B1.394 (2)
O51D—N5D1.226 (2)C21B—C31B1.366 (2)
O52D—N5D1.235 (2)C31B—C41B1.399 (2)
O2D—H2D0.90 (2)C41B—C51B1.404 (2)
N1A—C2A1.350 (2)C51B—C61B1.370 (2)
N1A—C6A1.3539 (19)C5B—H5B0.9500
N2A—C2A1.360 (2)C21B—H21B0.9500
N3A—C4A1.3473 (19)C31B—H31B0.9500
N3A—C2A1.3242 (19)C42B—H45B0.9800
N41A—C41A1.370 (2)C42B—H44B0.9800
N1A—H1A0.939 (18)C42B—H43B0.9800
N2A—H2A0.85 (2)C51B—H51B0.9500
N41A—H41A0.82 (3)C61B—H61B0.9500
N41A—H42A0.89 (2)C62B—H65B0.9800
N1B—C6B1.350 (2)C62B—H63B0.9800
N1B—C2B1.354 (2)C62B—H64B0.9800
N2B—C2B1.355 (2)C1C—C11C1.501 (2)
N3B—C2B1.3264 (19)C1C—C6C1.386 (2)
N3B—C4B1.344 (2)C1C—C2C1.410 (2)
N41B—C41B1.367 (2)C2C—C3C1.400 (2)
N1B—H1B0.91 (2)C3C—C4C1.367 (2)
N2B—H2B0.889 (19)C4C—C5C1.393 (3)
N41B—H41B0.89 (2)C5C—C6C1.380 (2)
N41B—H42B0.83 (2)C3C—H3C0.9500
N5C—C5C1.453 (2)C4C—H4C0.9500
N5D—C5D1.454 (2)C6C—H6C0.9500
C4A—C5A1.392 (2)C1D—C6D1.390 (2)
C4A—C42A1.488 (2)C1D—C11D1.501 (2)
C5A—C6A1.375 (2)C1D—C2D1.410 (2)
C6A—C62A1.490 (2)C2D—C3D1.404 (2)
C11A—C21A1.391 (2)C3D—C4D1.371 (2)
C11A—C61A1.399 (2)C4D—C5D1.392 (2)
C21A—C31A1.380 (2)C5D—C6D1.386 (2)
C31A—C41A1.402 (2)C3D—H3D0.9500
C41A—C51A1.398 (2)C4D—H4D0.9500
C51A—C61A1.373 (2)C6D—H6D0.9500
O11A—S1A—O12A120.00 (7)N1B—C2B—N2B116.83 (13)
O11A—S1A—N2A108.70 (7)N1B—C2B—N3B123.20 (14)
O11A—S1A—C11A108.90 (7)N3B—C4B—C42B115.81 (14)
O12A—S1A—N2A101.64 (7)C5B—C4B—C42B122.33 (14)
O12A—S1A—C11A109.63 (7)N3B—C4B—C5B121.86 (14)
N2A—S1A—C11A107.13 (7)C4B—C5B—C6B119.06 (14)
O11B—S1B—N2B108.92 (7)N1B—C6B—C5B117.86 (14)
O11B—S1B—C11B110.08 (7)C5B—C6B—C62B124.49 (14)
O12B—S1B—N2B101.66 (7)N1B—C6B—C62B117.64 (14)
O12B—S1B—C11B110.30 (7)S1B—C11B—C21B119.10 (12)
N2B—S1B—C11B105.78 (7)S1B—C11B—C61B120.80 (12)
O11B—S1B—O12B119.02 (7)C21B—C11B—C61B120.10 (14)
C2C—O2C—H2C105.0 (17)C11B—C21B—C31B119.84 (14)
C2D—O2D—H2D105.7 (14)C21B—C31B—C41B120.97 (15)
C2A—N1A—C6A120.37 (13)C31B—C41B—C51B118.65 (14)
S1A—N2A—C2A123.73 (11)N41B—C41B—C51B120.92 (15)
C2A—N3A—C4A117.13 (13)N41B—C41B—C31B120.41 (15)
C6A—N1A—H1A118.6 (12)C41B—C51B—C61B120.48 (14)
C2A—N1A—H1A121.1 (12)C11B—C61B—C51B119.93 (14)
S1A—N2A—H2A116.0 (13)C4B—C5B—H5B120.00
C2A—N2A—H2A119.1 (14)C6B—C5B—H5B120.00
C41A—N41A—H41A119.8 (16)C31B—C21B—H21B120.00
H41A—N41A—H42A118 (2)C11B—C21B—H21B120.00
C41A—N41A—H42A114.8 (14)C21B—C31B—H31B120.00
C2B—N1B—C6B120.75 (14)C41B—C31B—H31B120.00
S1B—N2B—C2B123.29 (11)C4B—C42B—H43B109.00
C2B—N3B—C4B117.23 (13)C4B—C42B—H44B109.00
C6B—N1B—H1B120.0 (13)H43B—C42B—H44B109.00
C2B—N1B—H1B119.2 (13)C4B—C42B—H45B110.00
C2B—N2B—H2B123.3 (13)H44B—C42B—H45B110.00
S1B—N2B—H2B113.2 (13)H43B—C42B—H45B109.00
C41B—N41B—H42B118.5 (14)C61B—C51B—H51B120.00
C41B—N41B—H41B113.6 (15)C41B—C51B—H51B120.00
H41B—N41B—H42B126 (2)C11B—C61B—H61B120.00
O51C—N5C—C5C118.80 (16)C51B—C61B—H61B120.00
O52C—N5C—C5C118.44 (15)H63B—C62B—H65B109.00
O51C—N5C—O52C122.77 (15)H64B—C62B—H65B109.00
O51D—N5D—O52D122.88 (14)C6B—C62B—H64B109.00
O51D—N5D—C5D118.78 (15)H63B—C62B—H64B109.00
O52D—N5D—C5D118.33 (13)C6B—C62B—H65B110.00
N2A—C2A—N3A119.57 (14)C6B—C62B—H63B110.00
N1A—C2A—N2A116.84 (13)C2C—C1C—C11C121.10 (14)
N1A—C2A—N3A123.59 (13)C6C—C1C—C11C120.09 (14)
N3A—C4A—C5A121.85 (14)C2C—C1C—C6C118.81 (14)
N3A—C4A—C42A116.05 (14)O2C—C2C—C3C117.41 (14)
C5A—C4A—C42A122.10 (14)C1C—C2C—C3C120.42 (15)
C4A—C5A—C6A118.89 (14)O2C—C2C—C1C122.18 (14)
N1A—C6A—C62A117.56 (13)C2C—C3C—C4C120.33 (16)
N1A—C6A—C5A118.17 (14)C3C—C4C—C5C118.77 (16)
C5A—C6A—C62A124.25 (14)N5C—C5C—C6C119.24 (15)
S1A—C11A—C61A120.29 (12)C4C—C5C—C6C122.26 (15)
S1A—C11A—C21A119.64 (12)N5C—C5C—C4C118.49 (15)
C21A—C11A—C61A120.07 (14)C1C—C6C—C5C119.41 (15)
C11A—C21A—C31A119.73 (15)O12C—C11C—C1C116.00 (13)
C21A—C31A—C41A120.69 (16)O11C—C11C—O12C124.26 (14)
N41A—C41A—C51A121.05 (15)O11C—C11C—C1C119.73 (14)
N41A—C41A—C31A120.09 (16)C2C—C3C—H3C120.00
C31A—C41A—C51A118.82 (15)C4C—C3C—H3C120.00
C41A—C51A—C61A120.76 (14)C5C—C4C—H4C121.00
C11A—C61A—C51A119.92 (15)C3C—C4C—H4C121.00
C6A—C5A—H5A121.00C1C—C6C—H6C120.00
C4A—C5A—H5A121.00C5C—C6C—H6C120.00
C31A—C21A—H21A120.00C2D—C1D—C11D121.32 (14)
C11A—C21A—H21A120.00C6D—C1D—C11D119.92 (14)
C41A—C31A—H31A120.00C2D—C1D—C6D118.77 (14)
C21A—C31A—H31A120.00O2D—C2D—C1D122.23 (14)
H43A—C42A—H45A110.00O2D—C2D—C3D117.38 (14)
C4A—C42A—H44A109.00C1D—C2D—C3D120.39 (15)
H44A—C42A—H45A109.00C2D—C3D—C4D120.31 (16)
C4A—C42A—H43A109.00C3D—C4D—C5D118.98 (16)
C4A—C42A—H45A109.00N5D—C5D—C6D119.27 (14)
H43A—C42A—H44A109.00C4D—C5D—C6D121.93 (15)
C61A—C51A—H51A120.00N5D—C5D—C4D118.78 (14)
C41A—C51A—H51A120.00C1D—C6D—C5D119.61 (14)
C51A—C61A—H61A120.00O11D—C11D—C1D120.77 (14)
C11A—C61A—H61A120.00O12D—C11D—C1D115.61 (13)
C6A—C62A—H63A109.00O11D—C11D—O12D123.62 (14)
C6A—C62A—H64A109.00C2D—C3D—H3D120.00
H63A—C62A—H64A109.00C4D—C3D—H3D120.00
H64A—C62A—H65A109.00C3D—C4D—H4D120.00
C6A—C62A—H65A110.00C5D—C4D—H4D121.00
H63A—C62A—H65A109.00C1D—C6D—H6D120.00
N2B—C2B—N3B119.97 (14)C5D—C6D—H6D120.00
O11A—S1A—N2A—C2A51.52 (14)C11A—C21A—C31A—C41A1.7 (2)
O12A—S1A—N2A—C2A179.01 (12)C21A—C31A—C41A—C51A1.4 (2)
C11A—S1A—N2A—C2A66.00 (14)C21A—C31A—C41A—N41A176.06 (16)
O11A—S1A—C11A—C21A160.97 (12)N41A—C41A—C51A—C61A177.13 (16)
O11A—S1A—C11A—C61A18.27 (15)C31A—C41A—C51A—C61A0.3 (2)
O12A—S1A—C11A—C21A27.88 (15)C41A—C51A—C61A—C11A0.5 (2)
O12A—S1A—C11A—C61A151.36 (13)C42B—C4B—C5B—C6B178.39 (15)
N2A—S1A—C11A—C21A81.64 (14)N3B—C4B—C5B—C6B1.7 (2)
N2A—S1A—C11A—C61A99.12 (14)C4B—C5B—C6B—C62B179.08 (15)
N2B—S1B—C11B—C21B78.04 (14)C4B—C5B—C6B—N1B0.0 (2)
N2B—S1B—C11B—C61B102.11 (14)C21B—C11B—C61B—C51B0.7 (2)
O11B—S1B—N2B—C2B59.70 (14)S1B—C11B—C21B—C31B178.54 (12)
O12B—S1B—N2B—C2B173.83 (12)C61B—C11B—C21B—C31B1.3 (2)
C11B—S1B—N2B—C2B58.59 (14)S1B—C11B—C61B—C51B179.14 (12)
O11B—S1B—C11B—C21B164.44 (12)C11B—C21B—C31B—C41B0.2 (2)
O11B—S1B—C11B—C61B15.41 (15)C21B—C31B—C41B—C51B1.4 (2)
O12B—S1B—C11B—C21B31.14 (15)C21B—C31B—C41B—N41B176.95 (16)
O12B—S1B—C11B—C61B148.71 (13)C31B—C41B—C51B—C61B2.0 (2)
C2A—N1A—C6A—C5A0.00 (19)N41B—C41B—C51B—C61B176.33 (16)
C2A—N1A—C6A—C62A178.53 (13)C41B—C51B—C61B—C11B1.0 (2)
C6A—N1A—C2A—N3A0.2 (2)C6C—C1C—C2C—O2C178.79 (14)
C6A—N1A—C2A—N2A179.44 (13)C6C—C1C—C2C—C3C1.2 (2)
S1A—N2A—C2A—N3A12.4 (2)C2C—C1C—C11C—O11C177.96 (14)
S1A—N2A—C2A—N1A168.33 (11)C2C—C1C—C11C—O12C1.8 (2)
C2A—N3A—C4A—C5A0.9 (2)C6C—C1C—C11C—O11C1.9 (2)
C4A—N3A—C2A—N1A0.3 (2)C6C—C1C—C11C—O12C178.37 (14)
C4A—N3A—C2A—N2A178.99 (13)C11C—C1C—C2C—O2C1.4 (2)
C2A—N3A—C4A—C42A178.67 (14)C11C—C1C—C2C—C3C178.65 (14)
C6B—N1B—C2B—N3B0.2 (2)C2C—C1C—C6C—C5C1.0 (2)
C2B—N1B—C6B—C5B0.7 (2)C11C—C1C—C6C—C5C178.79 (13)
C6B—N1B—C2B—N2B178.90 (13)O2C—C2C—C3C—C4C179.05 (14)
C2B—N1B—C6B—C62B179.89 (13)C1C—C2C—C3C—C4C0.9 (2)
S1B—N2B—C2B—N1B176.82 (10)C2C—C3C—C4C—C5C0.5 (2)
S1B—N2B—C2B—N3B2.3 (2)C3C—C4C—C5C—C6C0.4 (2)
C2B—N3B—C4B—C5B2.5 (2)C3C—C4C—C5C—N5C179.12 (14)
C2B—N3B—C4B—C42B177.57 (14)N5C—C5C—C6C—C1C179.38 (13)
C4B—N3B—C2B—N2B177.27 (13)C4C—C5C—C6C—C1C0.7 (2)
C4B—N3B—C2B—N1B1.8 (2)C6D—C1D—C2D—O2D179.26 (15)
O51C—N5C—C5C—C6C178.18 (15)C6D—C1D—C2D—C3D0.2 (2)
O51C—N5C—C5C—C4C0.6 (2)C11D—C1D—C2D—O2D0.5 (2)
O52C—N5C—C5C—C4C179.97 (16)C11D—C1D—C2D—C3D180.00 (15)
O52C—N5C—C5C—C6C1.3 (2)C2D—C1D—C6D—C5D0.8 (2)
O51D—N5D—C5D—C6D176.04 (15)C11D—C1D—C6D—C5D179.02 (14)
O52D—N5D—C5D—C6D2.8 (2)C2D—C1D—C11D—O11D179.30 (15)
O51D—N5D—C5D—C4D2.9 (2)C2D—C1D—C11D—O12D1.1 (2)
O52D—N5D—C5D—C4D178.27 (14)C6D—C1D—C11D—O11D0.9 (2)
N3A—C4A—C5A—C6A1.0 (2)C6D—C1D—C11D—O12D178.73 (14)
C42A—C4A—C5A—C6A178.48 (15)O2D—C2D—C3D—C4D178.60 (15)
C4A—C5A—C6A—C62A177.87 (14)C1D—C2D—C3D—C4D0.9 (2)
C4A—C5A—C6A—N1A0.6 (2)C2D—C3D—C4D—C5D0.6 (2)
C21A—C11A—C61A—C51A0.3 (2)C3D—C4D—C5D—N5D178.47 (14)
S1A—C11A—C61A—C51A178.96 (12)C3D—C4D—C5D—C6D0.4 (2)
S1A—C11A—C21A—C31A179.96 (13)N5D—C5D—C6D—C1D177.77 (13)
C61A—C11A—C21A—C31A0.8 (2)C4D—C5D—C6D—C1D1.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O12D0.939 (18)1.647 (18)2.5847 (17)176 (2)
N1B—H1B···O12C0.91 (2)1.71 (2)2.6162 (18)176.4 (18)
N2A—H2A···O11D0.85 (2)1.94 (2)2.7810 (18)177 (2)
N2B—H2B···O11C0.889 (19)1.836 (19)2.7221 (18)174.3 (18)
N41A—H41A···O11Di0.82 (3)2.57 (2)3.217 (2)138 (2)
N41B—H41B···O2Cii0.89 (2)2.49 (2)3.269 (2)147 (2)
N41B—H42B···O12Biii0.83 (2)2.45 (2)3.106 (2)136.6 (18)
O2C—H2C···O12C0.89 (3)1.70 (3)2.5223 (17)152 (2)
O2D—H2D···O12D0.90 (2)1.70 (2)2.5215 (17)151 (2)
C5A—H5A···O52Div0.952.563.4175 (19)150
C5B—H5B···O51Cv0.952.443.348 (2)160
C5B—H5B···O52Cv0.952.583.420 (2)147
C42A—H43A···O52Div0.982.493.428 (2)159
C42B—H45B···O52Cv0.982.423.350 (2)158
C61A—H61A···O11A0.952.592.9422 (19)102
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x1/2, y+1/2, z1/2; (iii) x+3/2, y+1/2, z+3/2; (iv) x, y1, z; (v) x, y+1, z.
(II) 2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate top
Crystal data top
C12H15N4O2S+·C6H2N3O7F(000) = 1048
Mr = 507.45Dx = 1.584 Mg m3
Monoclinic, P21/cMelting point = 469–471 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.3131 (2) ÅCell parameters from 7676 reflections
b = 19.2779 (5) Åθ = 3.2–28.8°
c = 13.4483 (4) ŵ = 0.22 mm1
β = 99.158 (3)°T = 200 K
V = 2127.74 (10) Å3Block, yellow
Z = 40.35 × 0.35 × 0.26 mm
Data collection top
Oxford Gemini-S CCD area-detector
diffractometer
4171 independent reflections
Radiation source: Enhance (Mo) X-ray source3318 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.3°
ω scansh = 810
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 2323
Tmin = 0.970, Tmax = 0.981l = 1516
14211 measured reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.1041P]
where P = (Fo2 + 2Fc2)/3
4171 reflections(Δ/σ)max = 0.005
334 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C12H15N4O2S+·C6H2N3O7V = 2127.74 (10) Å3
Mr = 507.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3131 (2) ŵ = 0.22 mm1
b = 19.2779 (5) ÅT = 200 K
c = 13.4483 (4) Å0.35 × 0.35 × 0.26 mm
β = 99.158 (3)°
Data collection top
Oxford Gemini-S CCD area-detector
diffractometer
4171 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
3318 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.981Rint = 0.024
14211 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.27 e Å3
4171 reflectionsΔρmin = 0.42 e Å3
334 parameters
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

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)
S1A1.01736 (5)0.72633 (2)0.40874 (3)0.0286 (1)
O11A1.01403 (16)0.74900 (6)0.30725 (10)0.0411 (4)
O12A0.91002 (15)0.75680 (6)0.46966 (11)0.0381 (4)
N1A0.81196 (16)0.54828 (6)0.42730 (11)0.0240 (4)
N2A0.96357 (18)0.64262 (7)0.39275 (12)0.0289 (5)
N3A0.95185 (16)0.61463 (7)0.56049 (10)0.0254 (4)
N41A1.6891 (2)0.73736 (9)0.62678 (16)0.0419 (6)
C2A0.90857 (19)0.60189 (8)0.46347 (13)0.0232 (5)
C4A0.89632 (19)0.57061 (8)0.62539 (13)0.0247 (5)
C5A0.79877 (19)0.51355 (8)0.59168 (13)0.0267 (5)
C6A0.75510 (18)0.50281 (8)0.49024 (13)0.0244 (5)
C11A1.2145 (2)0.72872 (8)0.47392 (13)0.0250 (5)
C21A1.3454 (2)0.72025 (8)0.42106 (13)0.0300 (6)
C31A1.5022 (2)0.72321 (9)0.47158 (14)0.0317 (6)
C41A1.5335 (2)0.73431 (8)0.57572 (13)0.0275 (5)
C42A0.9460 (2)0.58500 (9)0.73449 (13)0.0337 (6)
C51A1.4001 (2)0.74275 (8)0.62754 (14)0.0299 (6)
C61A1.2436 (2)0.73988 (8)0.57729 (13)0.0280 (5)
C62A0.6501 (2)0.44540 (9)0.44236 (15)0.0326 (6)
O10.81506 (14)0.55856 (6)0.23824 (9)0.0327 (4)
O210.51094 (17)0.58897 (8)0.28921 (10)0.0483 (5)
O220.35141 (16)0.52229 (7)0.18893 (11)0.0455 (5)
O410.33961 (17)0.59866 (9)0.16549 (11)0.0573 (6)
O420.56354 (17)0.63473 (7)0.20899 (10)0.0476 (5)
O611.06573 (16)0.58522 (8)0.01325 (11)0.0492 (5)
O621.06389 (16)0.62078 (8)0.16560 (11)0.0482 (5)
N20.46886 (17)0.56092 (7)0.20714 (11)0.0301 (5)
N40.48456 (19)0.61225 (8)0.14630 (12)0.0343 (5)
N60.99501 (17)0.59915 (8)0.08397 (12)0.0333 (5)
C10.7383 (2)0.57497 (8)0.15227 (12)0.0248 (5)
C20.56423 (19)0.57448 (8)0.12657 (12)0.0236 (5)
C30.4795 (2)0.58495 (8)0.03122 (13)0.0251 (5)
C40.5685 (2)0.60005 (8)0.04467 (13)0.0256 (5)
C50.7370 (2)0.60378 (8)0.02677 (13)0.0253 (5)
C60.81761 (19)0.59217 (8)0.06853 (13)0.0259 (5)
H42A1.706 (3)0.7434 (12)0.693 (2)0.061 (8)*
H1A0.784 (3)0.5461 (10)0.3591 (17)0.048 (6)*
H2A0.943 (2)0.6323 (10)0.3307 (16)0.037 (6)*
H5A0.763200.482600.638600.0320*
H21A1.325600.712500.350400.0360*
H31A1.590700.717700.435400.0380*
H41A1.771 (3)0.7388 (10)0.5900 (16)0.039 (6)*
H48A1.063700.578100.752900.0510*0.500
H43A0.888500.553300.773800.0510*0.500
H44A0.918400.633000.748800.0510*0.500
H45A0.850000.598200.764100.0510*0.500
H46A1.025300.623000.743200.0510*0.500
H47A0.995300.543300.768200.0510*0.500
H51A1.419100.750500.698200.0360*
H61A1.154700.745500.613100.0340*
H62A0.610500.417800.494700.0490*
H63A0.713600.415700.403900.0490*
H64A0.557100.464900.397000.0490*
H30.364000.581900.018000.0300*
H50.795800.614300.080000.0300*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0292 (2)0.0220 (2)0.0337 (3)0.0017 (2)0.0023 (2)0.0062 (2)
O11A0.0486 (8)0.0353 (7)0.0360 (8)0.0070 (6)0.0037 (6)0.0162 (6)
O12A0.0287 (7)0.0291 (7)0.0572 (9)0.0035 (5)0.0089 (6)0.0007 (6)
N1A0.0241 (7)0.0244 (7)0.0228 (8)0.0015 (5)0.0016 (6)0.0012 (6)
N2A0.0349 (8)0.0273 (8)0.0241 (9)0.0086 (6)0.0034 (7)0.0022 (6)
N3A0.0256 (7)0.0250 (7)0.0253 (8)0.0006 (6)0.0036 (6)0.0002 (6)
N41A0.0290 (9)0.0555 (11)0.0403 (11)0.0033 (7)0.0029 (8)0.0042 (8)
C2A0.0207 (8)0.0210 (8)0.0280 (9)0.0009 (6)0.0045 (7)0.0006 (6)
C4A0.0212 (8)0.0267 (8)0.0265 (9)0.0051 (6)0.0050 (7)0.0011 (7)
C5A0.0256 (9)0.0267 (9)0.0292 (10)0.0008 (6)0.0089 (7)0.0049 (7)
C6A0.0194 (8)0.0221 (8)0.0323 (10)0.0012 (6)0.0061 (7)0.0031 (7)
C11A0.0264 (9)0.0203 (8)0.0286 (10)0.0028 (6)0.0054 (7)0.0032 (7)
C21A0.0348 (10)0.0327 (9)0.0236 (10)0.0052 (7)0.0084 (7)0.0015 (7)
C31A0.0284 (9)0.0350 (10)0.0347 (11)0.0029 (7)0.0138 (8)0.0017 (8)
C41A0.0274 (9)0.0221 (8)0.0330 (10)0.0024 (6)0.0045 (7)0.0032 (7)
C42A0.0379 (10)0.0370 (10)0.0266 (10)0.0003 (8)0.0064 (8)0.0009 (8)
C51A0.0354 (10)0.0295 (9)0.0250 (10)0.0003 (7)0.0051 (8)0.0021 (7)
C61A0.0297 (9)0.0255 (9)0.0309 (10)0.0010 (7)0.0114 (8)0.0023 (7)
C62A0.0301 (9)0.0283 (9)0.0390 (11)0.0059 (7)0.0041 (8)0.0008 (8)
O10.0325 (7)0.0420 (7)0.0225 (7)0.0006 (5)0.0009 (5)0.0029 (5)
O210.0460 (8)0.0731 (10)0.0279 (8)0.0014 (7)0.0127 (6)0.0108 (7)
O220.0446 (8)0.0470 (8)0.0493 (9)0.0146 (6)0.0213 (7)0.0014 (6)
O410.0370 (9)0.0912 (12)0.0393 (9)0.0111 (8)0.0076 (7)0.0123 (8)
O420.0496 (8)0.0635 (9)0.0298 (8)0.0009 (7)0.0071 (7)0.0190 (7)
O610.0303 (7)0.0740 (10)0.0462 (9)0.0036 (6)0.0153 (7)0.0032 (7)
O620.0344 (8)0.0657 (9)0.0420 (9)0.0154 (6)0.0012 (6)0.0027 (7)
N20.0314 (8)0.0318 (8)0.0288 (9)0.0044 (6)0.0097 (7)0.0029 (6)
N40.0355 (9)0.0371 (8)0.0288 (9)0.0012 (7)0.0008 (7)0.0043 (7)
N60.0261 (8)0.0386 (8)0.0353 (9)0.0043 (6)0.0050 (7)0.0052 (7)
C10.0303 (9)0.0217 (8)0.0224 (9)0.0014 (6)0.0042 (7)0.0030 (6)
C20.0262 (9)0.0225 (8)0.0232 (9)0.0015 (6)0.0075 (7)0.0004 (6)
C30.0227 (8)0.0225 (8)0.0298 (10)0.0015 (6)0.0030 (7)0.0005 (7)
C40.0317 (10)0.0227 (8)0.0220 (9)0.0001 (7)0.0027 (7)0.0003 (7)
C50.0301 (9)0.0234 (8)0.0240 (9)0.0030 (6)0.0090 (7)0.0010 (7)
C60.0239 (9)0.0248 (8)0.0291 (10)0.0034 (6)0.0046 (7)0.0011 (7)
Geometric parameters (Å, º) top
S1A—O11A1.4292 (14)C11A—C61A1.389 (2)
S1A—O12A1.4301 (14)C11A—C21A1.401 (2)
S1A—N2A1.6792 (14)C21A—C31A1.372 (2)
S1A—C11A1.7318 (17)C31A—C41A1.400 (3)
O1—C11.269 (2)C41A—C51A1.410 (2)
O21—N21.229 (2)C51A—C61A1.368 (2)
O22—N21.221 (2)C5A—H5A0.9500
O41—N41.220 (2)C21A—H21A0.9500
O42—N41.227 (2)C31A—H31A0.9500
O61—N61.225 (2)C42A—H44A0.9800
O62—N61.228 (2)C42A—H48A0.9800
N1A—C2A1.351 (2)C42A—H43A0.9800
N1A—C6A1.355 (2)C42A—H47A0.9800
N2A—C2A1.367 (2)C42A—H45A0.9800
N3A—C4A1.350 (2)C42A—H46A0.9800
N3A—C2A1.320 (2)C51A—H51A0.9500
N41A—C41A1.366 (2)C61A—H61A0.9500
N1A—H1A0.91 (2)C62A—H62A0.9800
N2A—H2A0.85 (2)C62A—H63A0.9800
N41A—H42A0.89 (3)C62A—H64A0.9800
N41A—H41A0.90 (2)C1—C21.433 (2)
N2—C21.464 (2)C1—C61.432 (2)
N4—C41.451 (2)C2—C31.376 (2)
N6—C61.462 (2)C3—C41.384 (2)
C4A—C5A1.399 (2)C4—C51.385 (2)
C4A—C42A1.486 (2)C5—C61.367 (2)
C5A—C6A1.370 (2)C3—H30.9500
C6A—C62A1.491 (2)C5—H50.9500
O11A—S1A—O12A120.16 (8)C4A—C5A—H5A120.00
O11A—S1A—N2A101.96 (8)C11A—C21A—H21A120.00
O11A—S1A—C11A110.38 (8)C31A—C21A—H21A120.00
O12A—S1A—N2A106.88 (7)C41A—C31A—H31A120.00
O12A—S1A—C11A109.00 (8)C21A—C31A—H31A120.00
N2A—S1A—C11A107.56 (8)H43A—C42A—H44A109.00
C2A—N1A—C6A121.10 (15)H45A—C42A—H46A109.00
S1A—N2A—C2A125.08 (13)H45A—C42A—H47A109.00
C2A—N3A—C4A117.03 (14)H46A—C42A—H47A110.00
C6A—N1A—H1A122.8 (14)C4A—C42A—H47A109.00
C2A—N1A—H1A116.1 (14)H48A—C42A—H43A109.00
C2A—N2A—H2A120.8 (13)H48A—C42A—H44A110.00
S1A—N2A—H2A111.1 (13)C4A—C42A—H43A109.00
H42A—N41A—H41A122 (2)C4A—C42A—H44A109.00
C41A—N41A—H42A119.8 (16)C4A—C42A—H45A109.00
C41A—N41A—H41A117.5 (14)C4A—C42A—H46A109.00
O22—N2—C2118.04 (14)C4A—C42A—H48A109.00
O21—N2—O22123.55 (15)C41A—C51A—H51A120.00
O21—N2—C2118.41 (14)C61A—C51A—H51A120.00
O42—N4—C4118.33 (15)C51A—C61A—H61A120.00
O41—N4—O42123.30 (16)C11A—C61A—H61A120.00
O41—N4—C4118.36 (15)C6A—C62A—H63A110.00
O61—N6—O62123.76 (15)C6A—C62A—H64A109.00
O62—N6—C6118.33 (15)H62A—C62A—H64A109.00
O61—N6—C6117.87 (15)H63A—C62A—H64A109.00
N2A—C2A—N3A120.80 (15)H62A—C62A—H63A109.00
N1A—C2A—N2A115.75 (15)C6A—C62A—H62A109.00
N1A—C2A—N3A123.44 (15)O1—C1—C2124.07 (15)
N3A—C4A—C42A116.81 (14)O1—C1—C6123.16 (15)
C5A—C4A—C42A121.51 (15)C2—C1—C6112.68 (14)
N3A—C4A—C5A121.67 (15)N2—C2—C1117.87 (14)
C4A—C5A—C6A119.31 (15)N2—C2—C3117.30 (14)
N1A—C6A—C62A116.68 (15)C1—C2—C3124.83 (15)
N1A—C6A—C5A117.43 (14)C2—C3—C4117.63 (15)
C5A—C6A—C62A125.89 (15)N4—C4—C3119.69 (15)
S1A—C11A—C21A119.28 (13)N4—C4—C5118.47 (15)
S1A—C11A—C61A120.71 (13)C3—C4—C5121.84 (16)
C21A—C11A—C61A120.01 (16)C4—C5—C6119.07 (16)
C11A—C21A—C31A119.83 (16)N6—C6—C1119.34 (15)
C21A—C31A—C41A120.84 (16)N6—C6—C5116.80 (15)
C31A—C41A—C51A118.47 (16)C1—C6—C5123.86 (15)
N41A—C41A—C31A121.33 (16)C2—C3—H3121.00
N41A—C41A—C51A120.20 (17)C4—C3—H3121.00
C41A—C51A—C61A120.80 (17)C4—C5—H5120.00
C11A—C61A—C51A120.06 (16)C6—C5—H5120.00
C6A—C5A—H5A120.00
O11A—S1A—N2A—C2A162.41 (14)N3A—C4A—C5A—C6A1.5 (2)
O12A—S1A—N2A—C2A35.47 (17)C42A—C4A—C5A—C6A179.47 (15)
C11A—S1A—N2A—C2A81.46 (16)C4A—C5A—C6A—C62A178.97 (15)
O11A—S1A—C11A—C21A28.19 (15)C4A—C5A—C6A—N1A1.0 (2)
O11A—S1A—C11A—C61A150.90 (13)S1A—C11A—C21A—C31A178.90 (13)
O12A—S1A—C11A—C21A162.20 (12)C61A—C11A—C21A—C31A0.2 (2)
O12A—S1A—C11A—C61A16.88 (15)S1A—C11A—C61A—C51A178.95 (12)
N2A—S1A—C11A—C21A82.26 (14)C21A—C11A—C61A—C51A0.1 (2)
N2A—S1A—C11A—C61A98.65 (14)C11A—C21A—C31A—C41A0.3 (2)
C6A—N1A—C2A—N2A177.49 (14)C21A—C31A—C41A—C51A0.3 (2)
C6A—N1A—C2A—N3A1.2 (2)C21A—C31A—C41A—N41A180.00 (16)
C2A—N1A—C6A—C5A0.3 (2)C31A—C41A—C51A—C61A0.3 (2)
C2A—N1A—C6A—C62A179.73 (14)N41A—C41A—C51A—C61A179.94 (16)
S1A—N2A—C2A—N1A154.00 (12)C41A—C51A—C61A—C11A0.2 (2)
S1A—N2A—C2A—N3A27.3 (2)O1—C1—C2—N26.3 (2)
C4A—N3A—C2A—N1A0.7 (2)O1—C1—C2—C3172.77 (15)
C4A—N3A—C2A—N2A177.96 (15)C6—C1—C2—N2177.07 (13)
C2A—N3A—C4A—C5A0.7 (2)C6—C1—C2—C33.8 (2)
C2A—N3A—C4A—C42A179.73 (14)O1—C1—C6—N67.2 (2)
O21—N2—C2—C3138.41 (16)O1—C1—C6—C5173.80 (15)
O22—N2—C2—C1137.67 (15)C2—C1—C6—N6176.16 (14)
O22—N2—C2—C341.5 (2)C2—C1—C6—C52.8 (2)
O21—N2—C2—C142.4 (2)N2—C2—C3—C4177.92 (14)
O41—N4—C4—C310.9 (2)C1—C2—C3—C43.0 (2)
O42—N4—C4—C3170.19 (15)C2—C3—C4—N4179.35 (14)
O42—N4—C4—C510.0 (2)C2—C3—C4—C50.8 (2)
O41—N4—C4—C5168.93 (16)N4—C4—C5—C6179.78 (14)
O61—N6—C6—C530.7 (2)C3—C4—C5—C60.0 (2)
O62—N6—C6—C132.2 (2)C4—C5—C6—N6177.92 (14)
O62—N6—C6—C5146.91 (16)C4—C5—C6—C11.1 (2)
O61—N6—C6—C1150.26 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O10.91 (2)1.70 (2)2.5545 (19)154 (2)
N1A—H1A···O210.91 (2)2.46 (2)2.974 (2)116.2 (18)
N2A—H2A···O10.85 (2)2.07 (2)2.7661 (19)139.2 (17)
N2A—H2A···O620.85 (2)2.59 (2)3.319 (2)145.0 (15)
N41A—H41A···O12Ai0.90 (2)2.16 (2)3.035 (2)163 (2)
Symmetry code: (i) x+1, y, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC12H15N4O2S+·C7H4NO5C12H15N4O2S+·C6H2N3O7
Mr461.46507.45
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)200200
a, b, c (Å)13.1611 (2), 14.0977 (2), 22.1219 (3)8.3131 (2), 19.2779 (5), 13.4483 (4)
β (°) 90.094 (2) 99.158 (3)
V3)4104.52 (10)2127.74 (10)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.210.22
Crystal size (mm)0.35 × 0.35 × 0.150.35 × 0.35 × 0.26
Data collection
DiffractometerOxford Gemini-S Ultra CCD area-detector
diffractometer
Oxford Gemini-S CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.960, 0.9800.970, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
30179, 8057, 5991 14211, 4171, 3318
Rint0.0250.024
(sin θ/λ)max1)0.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.090, 0.95 0.034, 0.091, 1.04
No. of reflections80574171
No. of parameters621334
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.300.27, 0.42

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O12D0.939 (18)1.647 (18)2.5847 (17)176 (2)
N1B—H1B···O12C0.91 (2)1.71 (2)2.6162 (18)176.4 (18)
N2A—H2A···O11D0.85 (2)1.94 (2)2.7810 (18)177 (2)
N2B—H2B···O11C0.889 (19)1.836 (19)2.7221 (18)174.3 (18)
N41A—H41A···O11Di0.82 (3)2.57 (2)3.217 (2)138 (2)
N41B—H41B···O2Cii0.89 (2)2.49 (2)3.269 (2)147 (2)
N41B—H42B···O12Biii0.83 (2)2.45 (2)3.106 (2)136.6 (18)
O2C—H2C···O12C0.89 (3)1.70 (3)2.5223 (17)152 (2)
O2D—H2D···O12D0.90 (2)1.70 (2)2.5215 (17)151 (2)
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x1/2, y+1/2, z1/2; (iii) x+3/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O10.91 (2)1.70 (2)2.5545 (19)154 (2)
N1A—H1A···O210.91 (2)2.46 (2)2.974 (2)116.2 (18)
N2A—H2A···O10.85 (2)2.07 (2)2.7661 (19)139.2 (17)
N2A—H2A···O620.85 (2)2.59 (2)3.319 (2)145.0 (15)
N41A—H41A···O12Ai0.90 (2)2.16 (2)3.035 (2)163 (2)
Symmetry code: (i) x+1, y, z.
 

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