research communications
of bis[bis(4-azaniumylphenyl) sulfone] tetranitrate monohydrate
aUnité de Recherche Chimie de l'Environnement et Moléculaire, Structurale `CHEMS', Faculté des Sciences Exactes,Campus Chaabet Ersas, Université Frères Mentouri Constantine 1, 25000 Constantine, Algeria
*Correspondence e-mail: bendjeddoulamia@gmail.com
In the title compound, the hydrated tetra(nitrate) salt of dapsone (4,4′-diaminodiphenylsulfone), 2C12H14N2O2S2+·4NO3−·H2O {alternative name: bis[bis(4,4′-diazaniumylphenyl) sulfone] tetranitrate monohydrate}, the cations are conformationally similar, with comparable dihedral angles between the two benzene rings in each of 70.03 (18) and 69.69 (19)°. In the crystal, mixed cation–anion–water molecule layers lying parallel to the (001) plane are formed through N—H⋯O, O—H⋯O and C—H⋯O hydrogen-bonding interactions and these layers are further extended into an overall three-dimensional supramolecular network structure. Inter-ring π–π interactions are also present [minimum ring centroid separation = 3.693 (3) Å].
Keywords: dapsone; 4,4′-diphenylsulfones; crystal structure; protonation; hydrogen-bonding; nitrate salt.
CCDC reference: 1579678
1. Chemical context
Dapsone (4,4′-diaminodiphenylsulfone), a very weak Ka ca 2), is a drug that has been used to treat a diversity of diseases including tuberculosis, leprosy, malaria and AIDS-related pneumonia (Wilson et al., 1991). The of dapsone was first reported in 1970 (Dickenson et al., 1970) and redetermined a number of times (Bocelli & Cantoni, 1990; Su et al., 1992; Bertolasi et al., 1993). The structure of its partial (0.33) hydrate has also been determined (Kus'mina et al., 1981; Bel'skii et al., 1983). To the best of our knowledge there are no reported polymorphic forms of dapsone.
(pSulfones are good hydrogen-bond acceptors since their ability to participate as such in hydrogen-bonding interactions is increased by the highly polar nature of the sulfur–oxygen bond (Almarsson & Zaworotko, 2004; Eccles et al., 2010). In order to enrich the knowledge of such kinds of compound and to investigate the effect of hydrogen bonding on the chemical and structural features, we report here the synthesis and analysis of a new salt of dapsone, the hydrated dinitrate 2C12H14N2O2S2+·4NO3−·H2O. In terms of other compounds containing the ammonio-substituted dapsone cation species, only the mono-ammonio–dapsone salt 4-(4-aminophenylsulfonyl)anilinium 2-carboxy-4,6-dinitrophenolate monohydrate has been reported (Smith & Wermuth, 2013). Surprisingly, the literature has not revealed any other containing the (4,4′-diammonio)-substituted diphenylsulfone.
2. Structural commentary
The title compound crystallizes in the orthorhombic P212121 with two (4,4′-diammoniodiphenyl)sulfone cations (A and B), four nitrate anions and one water molecule (O1W) in the (Fig. 1). The diaminodiphenylsulfone unit is protonated at both N1 and N2 in A and N3 and N4 in B. The two cations are conformationally similar with the dihedral angles between the benzene rings of the anilinic moieties of cation A [defined by (N2/C1–C6) (Aa) and (N1/C7–C12) (Ab)] and cation B [defined by (N3/C13–C18) (Ba) and (N4/ C19–C24) (Bb)] are 70.03 (18) and 69.69 (19)°, respectively. As expected the anilinium groups are planar with maximum r.m.s. deviations of 0.0044, 0.0120, 0.0114 and 0.0072 Å, respectively.
3. Supramolecular features
The hydrogen-bonded supramolecular assembly in the crystal of the title compound is generated by a total of 28 independent interactions, dominated by anilinium N—H⋯O hydrogen bonds involving only nitro-O acceptors and a single water acceptor, but no sulfone O atoms are involved (Table 1). The water molecule forms two hydrogen bonds, to sulfone O1vi and nitro O12vii acceptors. The two cations A and B are associated through π–π interactions [ring centroid separation CgAb⋯CgBai = 3.693 (3) Å [symmetry code: (i) −x + 1, y + , −z + ] and form double cationic chain sub-structures that extend along the a-axis direction (Fig. 2). The water molecule O1W, which plays a dual role as both donor and acceptor in hydrogen-bonding interactions, bridges the cations via one sulfonyl group (Fig. 3) and also bridges one nitro group, giving the combination of the hydrogen-bond sequence N3—H⋯O1W/O1W—H⋯O1, involving a D22(5) bond motif (Fig. 3). The cations and anions are interlinked by the ammonio N—H⋯O(nitro) hydrogen bonds through rings and finite chains involving R12(4), R21(6), R22(7) and D(3) motifs (Fig. 4), generating a three-dimensional hydrogen-bonded network structure in which a number of C—H⋯O(nitro) interactions are also found (Fig. 5).
4. Database survey
A search of the Cambridge Structural Database (Version 5.38; Groom et al., 2016) shows 20 hits concerning the 4,4′-diaminodiphenyl sulfone. Only one containing a protonated dapsone species, the mono-cationic (4-ammonio-4′-amino-diphenyl)sulfone, a phenolate (Smith & Wermuth, 2013).
5. Synthesis and crystallization
Fe(NO3)3·9H2O (20.19 mg, 0.50 mmol) in EtOH (2 ml) was added dropwise to 4,4′-diaminodiphenyl sulfone (12.41 mg, 0.50 mmol) in EtOH (5 ml), with continuous stirring at room temperature for 72 h. Slow evaporation of this solution yielded yellow crystals suitable for X-ray analysis within 5 d.
6. Refinement
Crystal data, data collection and structure . The aromatic H atoms were placed at calculated positions with C—H fixed at 0.93 Å and Uiso(H) = 1.2Ueq(C). All N—H atoms were located by difference methods but were subsequently restrained in the with N—H = 0.89 Å and Uiso = 1.2Ueq(N). The H atoms of the water molecule were also located in a Fourier map and were allowed to ride with a restrained O—H bond length = 0.85 (1) Å and H⋯H = 1.39 (2) Å and Uiso(H) = 1.5 Ueq(O). Although not of relevance in this achiral compound, the Flack parameter (Flack, 1983) was determined as 0.02 (9) for 4494 Friedel pairs.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1579678
https://doi.org/10.1107/S2056989017014803/zs2390sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014803/zs2390Isup2.hkl
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision, 2004).2C12H14N2O2S2+·4NO3−·H2O | F(000) = 1592 |
Mr = 766.68 | Dx = 1.55 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4292 reflections |
a = 9.366 (5) Å | θ = 2.8–30.6° |
b = 15.203 (5) Å | µ = 0.25 mm−1 |
c = 23.070 (5) Å | T = 293 K |
V = 3285.1 (2) Å3 | Prism, yellow |
Z = 4 | 0.1 × 0.04 × 0.03 mm |
Bruker APEXII CCD diffractometer | 5434 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 30.6°, θmin = 2.8° |
φ and ω scans | h = −13→10 |
22152 measured reflections | k = −20→21 |
9858 independent reflections | l = −20→32 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.1089P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.201 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.94 e Å−3 |
9858 reflections | Δρmin = −0.29 e Å−3 |
466 parameters | Absolute structure: (Flack, 1983), 4494 Friedel pairs |
3 restraints | Absolute structure parameter: 0.02 (9) |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.30537 (10) | 0.66966 (6) | 0.36491 (3) | 0.0460 (2) | |
S2 | 0.73567 (13) | 0.33251 (6) | 0.34908 (4) | 0.0573 (3) | |
O1 | 0.1674 (3) | 0.6792 (2) | 0.33905 (11) | 0.0662 (8) | |
O2 | 0.3663 (4) | 0.74142 (16) | 0.39709 (11) | 0.0641 (8) | |
N1 | 0.7194 (4) | 0.6046 (2) | 0.17307 (13) | 0.0632 (9) | |
N2 | 0.2628 (4) | 0.3644 (2) | 0.52443 (12) | 0.0534 (8) | |
C1 | 0.2741 (4) | 0.4383 (2) | 0.48528 (13) | 0.0438 (8) | |
C2 | 0.2055 (5) | 0.4351 (2) | 0.43285 (15) | 0.0526 (11) | |
C3 | 0.2172 (4) | 0.5057 (2) | 0.39507 (14) | 0.0509 (13) | |
O3 | 0.6919 (4) | 0.25896 (17) | 0.38437 (12) | 0.0774 (10) | |
C4 | 0.2981 (4) | 0.5777 (2) | 0.41134 (13) | 0.0424 (7) | |
O4 | 0.8628 (4) | 0.3279 (2) | 0.31386 (12) | 0.0797 (10) | |
C5 | 0.3660 (4) | 0.5804 (2) | 0.46487 (14) | 0.0483 (8) | |
C6 | 0.3540 (4) | 0.5102 (2) | 0.50192 (14) | 0.0485 (8) | |
C7 | 0.4267 (4) | 0.6429 (2) | 0.30900 (13) | 0.0390 (7) | |
C8 | 0.3757 (4) | 0.6264 (2) | 0.25382 (14) | 0.0486 (8) | |
C9 | 0.4746 (4) | 0.6132 (3) | 0.20947 (15) | 0.0530 (9) | |
C10 | 0.6172 (4) | 0.6166 (2) | 0.22081 (15) | 0.0449 (8) | |
C11 | 0.6665 (4) | 0.6310 (3) | 0.27560 (16) | 0.0571 (10) | |
C12 | 0.5709 (5) | 0.6446 (3) | 0.32016 (16) | 0.0558 (12) | |
N3 | 0.2464 (4) | 0.3877 (2) | 0.18676 (13) | 0.0581 (8) | |
N4 | 0.8110 (4) | 0.6370 (2) | 0.50927 (13) | 0.0579 (8) | |
O5 | 0.5968 (3) | 0.7800 (2) | 0.49317 (12) | 0.0697 (8) | |
O6 | 0.7370 (4) | 0.7782 (2) | 0.41897 (13) | 0.0752 (9) | |
O7 | 0.5916 (4) | 0.88673 (19) | 0.43116 (13) | 0.0716 (8) | |
C13 | 0.3656 (5) | 0.3788 (2) | 0.22676 (15) | 0.0501 (9) | |
C14 | 0.5035 (5) | 0.3837 (3) | 0.20635 (15) | 0.0554 (10) | |
C15 | 0.6167 (5) | 0.3731 (2) | 0.24417 (15) | 0.0528 (9) | |
C16 | 0.5899 (5) | 0.3571 (2) | 0.30186 (14) | 0.0484 (9) | |
C17 | 0.4495 (5) | 0.3514 (3) | 0.32251 (15) | 0.0636 (11) | |
C18 | 0.3379 (5) | 0.3635 (3) | 0.28489 (17) | 0.0648 (11) | |
C19 | 0.7558 (4) | 0.4240 (2) | 0.39558 (14) | 0.0503 (9) | |
C20 | 0.8352 (5) | 0.4962 (3) | 0.37815 (16) | 0.0585 (10) | |
C21 | 0.8536 (5) | 0.5659 (3) | 0.41473 (16) | 0.0580 (10) | |
C22 | 0.7930 (4) | 0.5624 (2) | 0.46966 (16) | 0.0491 (8) | |
C23 | 0.7158 (5) | 0.4897 (3) | 0.48763 (15) | 0.0553 (10) | |
C24 | 0.6959 (5) | 0.4201 (3) | 0.45057 (15) | 0.0560 (9) | |
N5 | 0.6416 (4) | 0.8159 (2) | 0.44782 (13) | 0.0550 (8) | |
O8 | 0.3116 (4) | 0.2214 (2) | 0.42874 (15) | 0.0777 (12) | |
O9 | 0.4742 (4) | 0.2291 (2) | 0.49463 (14) | 0.0799 (9) | |
O10 | 0.4700 (3) | 0.1205 (2) | 0.43431 (13) | 0.0703 (8) | |
N6 | 0.4179 (4) | 0.1904 (2) | 0.45266 (14) | 0.0563 (8) | |
O11 | 1.0082 (4) | 0.1199 (3) | 0.39162 (15) | 0.0863 (14) | |
O12 | 0.9768 (4) | 0.1153 (3) | 0.29935 (14) | 0.0909 (11) | |
O13 | 0.8139 (3) | 0.0628 (2) | 0.35749 (13) | 0.0666 (7) | |
N7 | 0.9327 (4) | 0.0995 (3) | 0.34960 (16) | 0.0635 (9) | |
O14 | 1.2484 (3) | −0.05892 (19) | 0.38079 (11) | 0.0620 (7) | |
O15 | 1.0556 (4) | −0.1246 (3) | 0.40490 (17) | 0.1024 (13) | |
O16 | 1.0780 (4) | −0.0673 (3) | 0.32060 (17) | 0.0936 (11) | |
N8 | 1.1241 (4) | −0.0855 (2) | 0.36797 (18) | 0.0632 (9) | |
O1W | 0.9435 (4) | −0.2379 (3) | 0.27703 (17) | 0.0861 (10) | |
H1A | 0.69946 | 0.64248 | 0.14476 | 0.0760* | |
H1B | 0.71292 | 0.54993 | 0.15959 | 0.0760* | |
H1C | 0.80755 | 0.61427 | 0.18596 | 0.0760* | |
H2A | 0.26874 | 0.31454 | 0.50439 | 0.0640* | |
H2B | 0.33346 | 0.36669 | 0.55019 | 0.0640* | |
H2C | 0.17936 | 0.36658 | 0.54281 | 0.0640* | |
H3 | 0.15161 | 0.38603 | 0.42270 | 0.0630* | |
H4 | 0.17140 | 0.50466 | 0.35932 | 0.0612* | |
H6 | 0.41919 | 0.62942 | 0.47551 | 0.0580* | |
H7 | 0.39929 | 0.51103 | 0.53780 | 0.0580* | |
H8 | 0.27809 | 0.62423 | 0.24647 | 0.0580* | |
H9 | 0.44306 | 0.60197 | 0.17197 | 0.0640* | |
H11 | 0.76413 | 0.63164 | 0.28288 | 0.0690* | |
H12 | 0.60380 | 0.65478 | 0.35759 | 0.0670* | |
H3A | 0.26860 | 0.36256 | 0.15311 | 0.0700* | |
H3B | 0.22780 | 0.44444 | 0.18109 | 0.0700* | |
H3C | 0.16968 | 0.36146 | 0.20164 | 0.0700* | |
H4A | 0.75103 | 0.67985 | 0.49938 | 0.0690* | |
H4B | 0.90036 | 0.65667 | 0.50711 | 0.0690* | |
H4C | 0.79262 | 0.61977 | 0.54538 | 0.0690* | |
H14 | 0.52045 | 0.39426 | 0.16724 | 0.0660* | |
H15 | 0.71014 | 0.37657 | 0.23074 | 0.0630* | |
H17 | 0.43220 | 0.33958 | 0.36142 | 0.0760* | |
H18 | 0.24430 | 0.36140 | 0.29828 | 0.0780* | |
H20 | 0.87605 | 0.49724 | 0.34142 | 0.0700* | |
H21 | 0.90570 | 0.61489 | 0.40308 | 0.0690* | |
H23 | 0.67743 | 0.48804 | 0.52479 | 0.0660* | |
H24 | 0.64326 | 0.37130 | 0.46210 | 0.0670* | |
H1W | 1.012 (4) | −0.232 (4) | 0.3016 (18) | 0.1290* | |
H2W | 0.974 (6) | −0.262 (4) | 0.2464 (14) | 0.1290* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0579 (6) | 0.0387 (4) | 0.0416 (4) | 0.0132 (4) | 0.0042 (4) | 0.0004 (3) |
S2 | 0.0848 (8) | 0.0408 (4) | 0.0462 (4) | 0.0166 (5) | 0.0009 (5) | −0.0036 (4) |
O1 | 0.063 (2) | 0.0803 (19) | 0.0551 (14) | 0.0293 (16) | 0.0019 (13) | 0.0090 (14) |
O2 | 0.106 (2) | 0.0354 (12) | 0.0515 (14) | 0.0031 (14) | 0.0146 (15) | −0.0086 (11) |
N1 | 0.066 (2) | 0.066 (2) | 0.0571 (17) | 0.0138 (18) | 0.0114 (17) | 0.0058 (16) |
N2 | 0.057 (2) | 0.0562 (17) | 0.0471 (15) | −0.0021 (15) | 0.0056 (14) | 0.0091 (14) |
C1 | 0.048 (2) | 0.0424 (17) | 0.0409 (16) | 0.0046 (15) | 0.0074 (14) | 0.0033 (13) |
C2 | 0.060 (2) | 0.0470 (19) | 0.0507 (18) | −0.0112 (18) | −0.0043 (18) | −0.0008 (16) |
C3 | 0.061 (3) | 0.053 (2) | 0.0388 (16) | −0.0028 (18) | −0.0073 (16) | −0.0036 (15) |
O3 | 0.138 (3) | 0.0358 (13) | 0.0580 (15) | 0.0072 (16) | −0.0079 (19) | 0.0059 (12) |
C4 | 0.046 (2) | 0.0422 (17) | 0.0393 (15) | 0.0050 (15) | 0.0010 (14) | −0.0039 (13) |
O4 | 0.095 (2) | 0.081 (2) | 0.0631 (15) | 0.0410 (19) | 0.0049 (16) | −0.0148 (16) |
C5 | 0.053 (2) | 0.0477 (19) | 0.0444 (17) | −0.0042 (16) | −0.0104 (16) | 0.0013 (15) |
C6 | 0.055 (2) | 0.052 (2) | 0.0379 (16) | −0.0008 (17) | −0.0070 (15) | 0.0032 (15) |
C7 | 0.0455 (19) | 0.0329 (15) | 0.0386 (15) | 0.0020 (13) | −0.0010 (13) | 0.0015 (12) |
C8 | 0.041 (2) | 0.060 (2) | 0.0454 (17) | 0.0019 (17) | −0.0036 (15) | 0.0012 (16) |
C9 | 0.058 (3) | 0.064 (2) | 0.0377 (16) | 0.0023 (19) | −0.0045 (16) | −0.0064 (16) |
C10 | 0.044 (2) | 0.0390 (17) | 0.0517 (19) | 0.0063 (15) | 0.0092 (16) | 0.0058 (14) |
C11 | 0.044 (2) | 0.066 (2) | 0.061 (2) | 0.0043 (19) | −0.0061 (17) | −0.0006 (19) |
C12 | 0.057 (2) | 0.065 (2) | 0.0452 (17) | 0.0061 (19) | −0.0100 (17) | −0.0074 (17) |
N3 | 0.061 (2) | 0.063 (2) | 0.0504 (15) | −0.0046 (17) | 0.0062 (16) | −0.0037 (14) |
N4 | 0.060 (2) | 0.0552 (17) | 0.0588 (17) | 0.0040 (16) | −0.0192 (16) | −0.0112 (15) |
O5 | 0.071 (2) | 0.084 (2) | 0.0544 (15) | −0.0047 (17) | 0.0026 (15) | 0.0124 (15) |
O6 | 0.065 (2) | 0.088 (2) | 0.0731 (19) | 0.0049 (18) | 0.0114 (16) | −0.0076 (16) |
O7 | 0.084 (2) | 0.0550 (17) | 0.0759 (18) | 0.0000 (16) | −0.0108 (18) | 0.0090 (15) |
C13 | 0.066 (2) | 0.0405 (18) | 0.0444 (17) | −0.0001 (17) | 0.0082 (17) | −0.0025 (14) |
C14 | 0.070 (3) | 0.059 (2) | 0.0377 (16) | −0.011 (2) | 0.0049 (18) | 0.0057 (16) |
C15 | 0.062 (2) | 0.055 (2) | 0.0418 (17) | −0.0037 (19) | 0.0119 (17) | −0.0011 (16) |
C16 | 0.073 (3) | 0.0311 (15) | 0.0410 (16) | 0.0004 (16) | 0.0041 (17) | −0.0022 (13) |
C17 | 0.083 (3) | 0.069 (3) | 0.0386 (17) | 0.000 (2) | 0.0142 (19) | 0.0015 (18) |
C18 | 0.071 (3) | 0.074 (3) | 0.050 (2) | −0.001 (2) | 0.014 (2) | −0.0085 (19) |
C19 | 0.059 (2) | 0.0466 (18) | 0.0456 (17) | 0.0111 (18) | −0.0043 (17) | −0.0001 (15) |
C20 | 0.070 (3) | 0.055 (2) | 0.0510 (19) | 0.005 (2) | 0.0057 (19) | −0.0003 (17) |
C21 | 0.063 (3) | 0.048 (2) | 0.063 (2) | 0.0006 (19) | −0.0015 (19) | 0.0048 (18) |
C22 | 0.044 (2) | 0.0480 (19) | 0.0555 (19) | 0.0057 (16) | −0.0094 (17) | −0.0065 (16) |
C23 | 0.067 (3) | 0.056 (2) | 0.0435 (18) | −0.0021 (19) | 0.0001 (17) | −0.0053 (16) |
C24 | 0.065 (3) | 0.053 (2) | 0.0502 (19) | −0.0029 (19) | 0.0025 (18) | −0.0056 (16) |
N5 | 0.058 (2) | 0.063 (2) | 0.0449 (15) | −0.0029 (17) | −0.0085 (15) | −0.0002 (15) |
O8 | 0.066 (2) | 0.073 (2) | 0.094 (2) | 0.0072 (17) | −0.0080 (19) | 0.0010 (17) |
O9 | 0.076 (2) | 0.090 (2) | 0.0737 (18) | −0.0019 (19) | −0.0081 (18) | −0.0174 (18) |
O10 | 0.069 (2) | 0.0683 (19) | 0.0733 (17) | 0.0112 (16) | 0.0057 (16) | −0.0074 (15) |
N6 | 0.052 (2) | 0.057 (2) | 0.0606 (18) | −0.0048 (16) | 0.0093 (16) | 0.0007 (16) |
O11 | 0.063 (2) | 0.110 (3) | 0.086 (2) | −0.012 (2) | −0.0061 (19) | −0.013 (2) |
O12 | 0.082 (2) | 0.117 (3) | 0.0738 (19) | 0.017 (2) | 0.0103 (18) | 0.0278 (19) |
O13 | 0.0531 (18) | 0.0745 (19) | 0.0723 (17) | −0.0014 (15) | −0.0003 (15) | 0.0061 (15) |
N7 | 0.064 (2) | 0.064 (2) | 0.063 (2) | 0.0171 (19) | 0.0051 (19) | 0.0120 (18) |
O14 | 0.0541 (18) | 0.0684 (17) | 0.0635 (16) | −0.0024 (15) | 0.0120 (14) | −0.0060 (14) |
O15 | 0.096 (3) | 0.082 (2) | 0.130 (3) | −0.024 (2) | 0.054 (3) | −0.012 (2) |
O16 | 0.066 (2) | 0.116 (3) | 0.099 (2) | 0.007 (2) | −0.014 (2) | −0.026 (2) |
N8 | 0.054 (2) | 0.058 (2) | 0.078 (2) | 0.0040 (17) | 0.014 (2) | −0.0212 (19) |
O1W | 0.057 (2) | 0.077 (2) | 0.124 (3) | 0.0099 (17) | −0.007 (2) | −0.011 (2) |
S1—O1 | 1.431 (3) | C8—C7 | 1.383 (5) |
S1—O2 | 1.438 (3) | C8—C9 | 1.395 (5) |
S1—C4 | 1.762 (3) | C8—H8 | 0.93 |
S1—C7 | 1.766 (3) | N7—O12 | 1.254 (5) |
S2—O3 | 1.443 (3) | C22—C23 | 1.384 (6) |
S2—O4 | 1.444 (4) | C22—C21 | 1.390 (5) |
S2—C19 | 1.766 (4) | C20—C21 | 1.366 (5) |
S2—C16 | 1.787 (4) | C20—C19 | 1.386 (5) |
O13—N7 | 1.258 (5) | C20—H20 | 0.93 |
O14—N8 | 1.267 (5) | O16—N8 | 1.207 (5) |
O5—N5 | 1.253 (4) | C4—C3 | 1.383 (5) |
N1—C10 | 1.470 (5) | C13—C14 | 1.376 (6) |
N1—H1B | 0.89 | C13—C18 | 1.386 (5) |
N1—H1C | 0.89 | C13—N3 | 1.455 (5) |
N1—H1A | 0.89 | C3—H4 | 0.93 |
O9—N6 | 1.250 (4) | C14—C15 | 1.383 (6) |
N2—C1 | 1.445 (4) | C14—H14 | 0.93 |
N2—H2A | 0.89 | C15—C16 | 1.376 (5) |
N2—H2C | 0.89 | C15—H15 | 0.93 |
N2—H2B | 0.89 | C16—C17 | 1.401 (6) |
O6—N5 | 1.253 (4) | C24—C23 | 1.373 (5) |
O7—N5 | 1.235 (4) | C24—C19 | 1.388 (5) |
O10—N6 | 1.243 (4) | C24—H24 | 0.93 |
N4—C22 | 1.466 (5) | N8—O15 | 1.221 (5) |
N4—H4A | 0.89 | C9—C10 | 1.362 (6) |
N4—H4B | 0.89 | C9—H9 | 0.93 |
N4—H4C | 0.89 | C12—C7 | 1.375 (5) |
O8—N6 | 1.233 (5) | C12—C11 | 1.379 (6) |
O1W—H2W | 0.848 (10) | C12—H12 | 0.93 |
O1W—H1W | 0.859 (10) | C23—H23 | 0.93 |
C1—C2 | 1.371 (5) | C10—C11 | 1.363 (5) |
C1—C6 | 1.379 (5) | C21—H21 | 0.93 |
O11—N7 | 1.239 (5) | C11—H11 | 0.93 |
C2—C3 | 1.388 (5) | C17—C18 | 1.371 (6) |
C2—H3 | 0.93 | C17—H17 | 0.93 |
C5—C6 | 1.372 (5) | C18—H18 | 0.93 |
C5—C4 | 1.389 (5) | N3—H3C | 0.89 |
C5—H6 | 0.93 | N3—H3A | 0.89 |
C6—H7 | 0.93 | N3—H3B | 0.89 |
O1—S1—O2 | 119.81 (19) | C14—C13—C18 | 121.1 (4) |
O1—S1—C4 | 107.38 (19) | C14—C13—N3 | 119.9 (3) |
O2—S1—C4 | 107.65 (15) | C18—C13—N3 | 119.0 (4) |
O1—S1—C7 | 107.45 (16) | C4—C3—C2 | 119.1 (3) |
O2—S1—C7 | 107.26 (17) | C4—C3—H4 | 120.5 |
C4—S1—C7 | 106.61 (15) | C2—C3—H4 | 120.5 |
O3—S2—O4 | 120.9 (2) | C13—C14—C15 | 119.8 (3) |
O3—S2—C19 | 107.32 (16) | C13—C14—H14 | 120.1 |
O4—S2—C19 | 107.0 (2) | C15—C14—H14 | 120.1 |
O3—S2—C16 | 106.8 (2) | C16—C15—C14 | 119.4 (4) |
O4—S2—C16 | 107.32 (17) | C16—C15—H15 | 120.3 |
C19—S2—C16 | 106.67 (17) | C14—C15—H15 | 120.3 |
C10—N1—H1B | 109.5 | C15—C16—C17 | 120.7 (4) |
C10—N1—H1C | 109.5 | C15—C16—S2 | 119.1 (3) |
H1B—N1—H1C | 109.5 | C17—C16—S2 | 119.8 (3) |
C10—N1—H1A | 109.5 | C23—C24—C19 | 118.8 (4) |
H1B—N1—H1A | 109.5 | C23—C24—H24 | 120.6 |
H1C—N1—H1A | 109.5 | C19—C24—H24 | 120.6 |
C1—N2—H2A | 109.5 | O16—N8—O15 | 123.7 (5) |
C1—N2—H2C | 109.5 | O16—N8—O14 | 117.9 (4) |
H2A—N2—H2C | 109.5 | O15—N8—O14 | 118.4 (4) |
C1—N2—H2B | 109.5 | C10—C9—C8 | 120.3 (3) |
H2A—N2—H2B | 109.5 | C10—C9—H9 | 119.8 |
H2C—N2—H2B | 109.5 | C8—C9—H9 | 119.8 |
C22—N4—H4A | 109.5 | C7—C12—C11 | 119.7 (3) |
C22—N4—H4B | 109.5 | C7—C12—H12 | 120.2 |
H4A—N4—H4B | 109.5 | C11—C12—H12 | 120.2 |
C22—N4—H4C | 109.5 | C12—C7—C8 | 121.0 (3) |
H4A—N4—H4C | 109.5 | C12—C7—S1 | 119.4 (3) |
H4B—N4—H4C | 109.5 | C8—C7—S1 | 119.5 (3) |
H2W—O1W—H1W | 111 (3) | C24—C23—C22 | 120.0 (3) |
C2—C1—C6 | 121.9 (3) | C24—C23—H23 | 120 |
C2—C1—N2 | 119.3 (3) | C22—C23—H23 | 120 |
C6—C1—N2 | 118.8 (3) | O8—N6—O10 | 119.5 (4) |
C1—C2—C3 | 119.3 (3) | O8—N6—O9 | 120.5 (4) |
C1—C2—H3 | 120.4 | O10—N6—O9 | 120.0 (4) |
C3—C2—H3 | 120.4 | C20—C19—C24 | 121.0 (3) |
O7—N5—O5 | 120.9 (4) | C20—C19—S2 | 120.3 (3) |
O7—N5—O6 | 120.3 (4) | C24—C19—S2 | 118.6 (3) |
O5—N5—O6 | 118.8 (4) | C9—C10—C11 | 121.1 (3) |
C6—C5—C4 | 119.6 (3) | C9—C10—N1 | 119.3 (3) |
C6—C5—H6 | 120.2 | C11—C10—N1 | 119.6 (3) |
C4—C5—H6 | 120.2 | C20—C21—C22 | 118.8 (4) |
C5—C6—C1 | 119.1 (3) | C20—C21—H21 | 120.6 |
C5—C6—H7 | 120.4 | C22—C21—H21 | 120.6 |
C1—C6—H7 | 120.4 | C10—C11—C12 | 119.7 (4) |
C7—C8—C9 | 118.1 (4) | C10—C11—H11 | 120.1 |
C7—C8—H8 | 120.9 | C12—C11—H11 | 120.1 |
C9—C8—H8 | 120.9 | C18—C17—C16 | 119.5 (3) |
O11—N7—O12 | 119.2 (4) | C18—C17—H17 | 120.3 |
O11—N7—O13 | 120.2 (4) | C16—C17—H17 | 120.3 |
O12—N7—O13 | 120.6 (4) | C17—C18—C13 | 119.5 (4) |
C23—C22—C21 | 121.1 (3) | C17—C18—H18 | 120.3 |
C23—C22—N4 | 119.4 (3) | C13—C18—H18 | 120.3 |
C21—C22—N4 | 119.5 (4) | C13—N3—H3C | 109.5 |
C21—C20—C19 | 120.2 (4) | C13—N3—H3A | 109.5 |
C21—C20—H20 | 119.9 | H3C—N3—H3A | 109.5 |
C19—C20—H20 | 119.9 | C13—N3—H3B | 109.5 |
C3—C4—C5 | 121.0 (3) | H3C—N3—H3B | 109.5 |
C3—C4—S1 | 118.9 (3) | H3A—N3—H3B | 109.5 |
C5—C4—S1 | 120.0 (3) | ||
C6—C1—C2—C3 | 0.4 (6) | O1—S1—C7—C12 | 169.1 (3) |
N2—C1—C2—C3 | −179.5 (3) | O2—S1—C7—C12 | 39.0 (3) |
C4—C5—C6—C1 | −0.3 (6) | C4—S1—C7—C12 | −76.0 (3) |
C2—C1—C6—C5 | −0.3 (6) | O1—S1—C7—C8 | −6.5 (3) |
N2—C1—C6—C5 | 179.6 (3) | O2—S1—C7—C8 | −136.6 (3) |
C6—C5—C4—C3 | 0.7 (6) | C4—S1—C7—C8 | 108.3 (3) |
C6—C5—C4—S1 | 176.9 (3) | C19—C24—C23—C22 | 0.8 (6) |
O1—S1—C4—C3 | 36.4 (3) | C21—C22—C23—C24 | −1.2 (6) |
O2—S1—C4—C3 | 166.7 (3) | N4—C22—C23—C24 | 178.8 (4) |
C7—S1—C4—C3 | −78.5 (3) | C21—C20—C19—C24 | −1.2 (6) |
O1—S1—C4—C5 | −139.8 (3) | C21—C20—C19—S2 | −178.4 (3) |
O2—S1—C4—C5 | −9.6 (4) | C23—C24—C19—C20 | 0.4 (6) |
C7—S1—C4—C5 | 105.3 (3) | C23—C24—C19—S2 | 177.6 (3) |
C5—C4—C3—C2 | −0.6 (6) | O3—S2—C19—C20 | 161.2 (3) |
S1—C4—C3—C2 | −176.8 (3) | O4—S2—C19—C20 | 30.0 (4) |
C1—C2—C3—C4 | 0.0 (6) | C16—S2—C19—C20 | −84.6 (4) |
C18—C13—C14—C15 | 0.2 (6) | O3—S2—C19—C24 | −16.0 (4) |
N3—C13—C14—C15 | −178.4 (3) | O4—S2—C19—C24 | −147.2 (3) |
C13—C14—C15—C16 | 0.3 (6) | C16—S2—C19—C24 | 98.2 (3) |
C14—C15—C16—C17 | 0.2 (6) | C8—C9—C10—C11 | 1.5 (6) |
C14—C15—C16—S2 | 173.8 (3) | C8—C9—C10—N1 | −178.5 (3) |
O3—S2—C16—C15 | −135.2 (3) | C19—C20—C21—C22 | 0.8 (6) |
O4—S2—C16—C15 | −4.1 (3) | C23—C22—C21—C20 | 0.4 (6) |
C19—S2—C16—C15 | 110.3 (3) | N4—C22—C21—C20 | −179.6 (4) |
O3—S2—C16—C17 | 38.5 (3) | C9—C10—C11—C12 | −1.7 (6) |
O4—S2—C16—C17 | 169.5 (3) | N1—C10—C11—C12 | 178.3 (3) |
C19—S2—C16—C17 | −76.1 (3) | C7—C12—C11—C10 | 0.4 (6) |
C7—C8—C9—C10 | 0.0 (6) | C15—C16—C17—C18 | −1.2 (6) |
C11—C12—C7—C8 | 1.0 (6) | S2—C16—C17—C18 | −174.8 (3) |
C11—C12—C7—S1 | −174.6 (3) | C16—C17—C18—C13 | 1.7 (6) |
C9—C8—C7—C12 | −1.2 (5) | C14—C13—C18—C17 | −1.3 (6) |
C9—C8—C7—S1 | 174.4 (3) | N3—C13—C18—C17 | 177.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O8i | 0.89 | 2.0800 | 2.959 (4) | 169 |
N1—H1A···O10i | 0.89 | 2.4400 | 3.057 (4) | 127 |
N1—H1B···O14ii | 0.89 | 1.9300 | 2.796 (4) | 163 |
N1—H1C···O12ii | 0.89 | 2.0500 | 2.920 (5) | 166 |
N2—H2A···O8 | 0.89 | 2.2800 | 3.132 (4) | 160 |
N2—H2A···O9 | 0.89 | 2.3300 | 2.937 (5) | 125 |
N2—H2B···O11iii | 0.89 | 2.1300 | 3.015 (5) | 176 |
N2—H2B···O13iii | 0.89 | 2.3900 | 2.979 (4) | 124 |
N2—H2C···O9iii | 0.89 | 2.5600 | 3.086 (5) | 119 |
N2—H2C···O10iii | 0.89 | 2.0400 | 2.912 (5) | 166 |
N3—H3A···O6iv | 0.89 | 2.1000 | 2.957 (4) | 161 |
N3—H3A···O7iv | 0.89 | 2.3700 | 3.115 (5) | 141 |
N3—H3B···O13i | 0.89 | 2.0500 | 2.906 (4) | 163 |
N3—H3C···O1Wi | 0.89 | 1.9100 | 2.740 (5) | 154 |
N4—H4A···O5 | 0.89 | 2.1000 | 2.982 (4) | 169 |
N4—H4A···O6 | 0.89 | 2.3900 | 3.071 (4) | 134 |
N4—H4B···O5v | 0.89 | 2.0800 | 2.960 (5) | 171 |
N4—H4B···O7v | 0.89 | 2.3800 | 2.988 (5) | 125 |
N4—H4C···O14iii | 0.89 | 1.9800 | 2.861 (4) | 169 |
N4—H4C···O15iii | 0.89 | 2.5000 | 3.111 (5) | 126 |
O1W—H1W···O1vi | 0.86 (4) | 2.18 (5) | 2.834 (5) | 133 (5) |
O1W—H2W···O12vii | 0.85 (4) | 2.19 (6) | 2.940 (6) | 147 (5) |
C9—H9···O10i | 0.93 | 2.6000 | 3.359 (5) | 139 |
C9—H9···O13i | 0.93 | 2.5700 | 3.206 (5) | 126 |
C14—H14···O7iv | 0.93 | 2.5000 | 3.295 (5) | 143 |
C14—H14···O14ii | 0.93 | 2.5300 | 3.194 (5) | 128 |
C15—H15···O16ii | 0.93 | 2.4600 | 3.351 (6) | 160 |
C23—H23···O14iii | 0.93 | 2.5200 | 3.227 (4) | 133 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) x+1, y−1, z; (vii) −x+2, y−1/2, −z+1/2. |
Acknowledgements
This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Frères Mentouri Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie, Algérie) for financial support via the PNR program.
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