research communications
A m-chlorobenzoic acid and furosemide
of nonahydrated disodium(II) with mixed anions fromaEnvironmental Toxicology PhD Program and the Health Research Center, Southern University and A&M College, Baton Rouge, LA 70813, USA, bSchool of Science, Hampton University, Hampton, VA 23668, USA, and cDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: rao_uppu@subr.edu
In the title compound, [Na2(H2O)9](C7H4ClO2)(C12H10ClN2O5S) {systematic name: catena-poly[[[triaquasodium(I)]-di-μ-aqua-[triaquasodium(I)]-μ-aqua] 3-chlorobenzoate 4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoate]}, both the original m-chlorobenzoic acid and furosemide exist with deprotonated carboxylates, and the sodium cations and water molecules exist in chains with stoichiometry [Na2(OH2)9]2+ that propagate in the [-110] direction. Each of the two independent Na+ ions is coordinated by three monodentate water molecules, two double-water bridges, and one single-water bridge. There is considerable cross-linking between the [Na2(OH2)9]2+ chains and to furosemide sulfonamide and carboxylate by intermolecular O—H⋯O hydrogen bonds. All hydrogen-bond donors participate in a complex two-dimensional array parallel to the ab plane. The furosemide NH group donates an intramolecular hydrogen bond to the carboxylate group, and the furosemide NH2 group donates an intramolecular hydrogen bond to the Cl atom and an intermolecular one to the m-chlorobenzoate O atom. The plethora of hydrogen-bond donors on the cation/water chain leads to many large rings, up to graph set R44(24), involving two chains and two furosemide anions. The chlorobenzoate is involved in only one R22(8) ring, with two water molecules cis-coordinated to Na. The furan O atom is not hydrogen bonded.
Keywords: crystal structure; loop diuretics; co-crystals; pharmaceutical formulations; hydrogen bonding.
CCDC reference: 1425658
1. Chemical context
Furosemide is a widely used diuretic for the treatment of hypertension and edema (Krumlovsky & del Greco, 1976; Musini et al., 2015), and to a lesser extent, hypercalcemia (Belen et al., 2014; Carvalhana et al., 2006). While this furan-containing compound is of interest, the toxicity elicited by these core compounds is not well understood. The free furan itself is a known hepato-carcinogen and toxicant, as studied in rats (Gill et al., 2010) and mice (Terrell et al., 2014). The epoxide metabolite of furans, formed in CYP450-mediated oxidations, can isomerize to highly reactive electrophilic intermediates such as cis-2-butene-1,4-dial (Chen et al., 1995; Peterson 2015; Vargas et al., 1998).
We have performed the oxidation of furosemide with m-chloroperbenzoic acid (m-CPBA), and isolated various epoxide and isomerized products in support of our efforts to understand this type of toxicity mechanism, and to also identify potential biomarkers for furosemide in humans. During the separation and drying of the products of the furosemide–m-CPBA reaction, we observed the formation of crystals in the mother liquor (the organic layer). Analysis of these crystals by X-ray crystallography revealed a disodium nonahydrate with furosemide (starting material) and m-chlorobenzoic acid (an inadvertent contaminant or the reduced product of m-CPBA). Analogous to the known properties of co-crystals of furosemide with nicotinamide and their pharmaceutical importance (Aitipamula et al., 2012; Chadha et al., 2012; Goud et al., 2012; Stepanovs & Mishnev, 2012; Ueto et al., 2012), we believe that the co-crystals of furosemide with m-chlorobenzoic acid could have useful applications in drug development and may lead to formulations with improved potency, solubility, and stability. Therefore, this serendipitous finding may have important applications for improving furosemide bioavailability.
2. Structural commentary
The . The furosemide moiety is present as the monoanion, with the COOH group deprotonated, N2 as NH and the primary amine nitrogen N1 as NH2. The m-chlorobenzoic acid moiety is also deprotonated. Balancing the charge of the two types of anions are two independent sodium cations, both of which are hexacoordinate, with Na⋯O(water) distances in the range 2.3558 (13)–2.4500 (13) Å. Each Na+ cation is coordinated by three monodentate water molecules, two double-water bridge molecules, and one single-water bridge molecule, as shown in Fig. 2. Thus, centrosymmetric Na2(OH2)8 units are linked by single water bridges, forming chains in the [10] direction.
is illustrated in Fig. 13. Supramolecular features
Hydrogen bonding is extensive (Table 1), with all 21 hydrogen-bond donors involved. Notable features of the two-dimensional hydrogen-bonding pattern (Etter et al.. 1990) are sulfonamide N—H⋯O bonds to m-chlorobenzoate, secondary amine N—H⋯O hydrogen bonds to furosemide anion (carboxylate), and water O—H⋯O hydrogen bonds to the sulfonamide O atom, to both types of carboxylates, and to other water molecules. The direction of the normal to the hydrogen-bonding network is [001]. The furan oxygen atom O5 is not involved in the hydrogen bonding. A supramolecular layer in the ab plane is shown in Fig. 3.
4. Synthesis and crystallization
Furosemide (8.2 mmol; 2.71 g), dissolved in 3 ml of dichloromethane (DCM), was added dropwise over 5 min to a solution of 8.2 mmol of m-CPBA (1.84 g) and 10.5 mmol NaHCO3 (0.88 g) in 20 ml of DCM on ice with rapid stirring (Fig. 4). After 2 h, an additional 4 mmol of m-CPBA in 10 ml of DCM was added to the reaction mixture. Upon removal from the ice bath, 4 ml of aqueous sodium sulfite solution (10%) was added with stirring for an additional 15 min. After partitioning the layers with deionized water (resistance 18.2 M Ω cm−1), the organic layer was collected and the aqueous layer was extracted with another 10 ml of DCM. The combined mixture of the organic layer was washed with 10 ml of aqueous solution of NaHCO3 (5%, w/v), dried over anhydrous Na2SO4, and then subjected to partial evaporation under low pressure (ca 4 psi) at 308 K. The partially evaporated sample was left at ambient pressure and temperature overnight. Crystals were formed with slow evaporation.
5. Refinement
Crystal data, data collection and structure . H atoms on C were idealized with C—H distances of 0.95 Å for sp2 C and 0.99 Å for CH2. Those on N and O were assigned from difference maps, and their positions refined, with O—H distances restrained to be equal. Uiso(H) were assigned as 1.2 times Ueq of the attached atoms (1.5 for water). Six reflections with Fo<<Fc were omitted from the calculations.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1425658
10.1107/S2056989015017430/pk2557sup1.cif
contains datablocks New_Global_Publ_Block, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017430/pk2557Isup2.hkl
Furosemide is a widely used diuretic for the treatment of hypertension and edema (Krumlovsky & del Greco, 1976; Musini et al., 2015), and to a lesser extent, hypercalcemia (Belen et al., 2014; Carvalhana et al. (2006)). This furan-containing compound is of interest; however, the toxicity elicited by these core compounds is not well understood. The free furan itself is a known hepato-carcinogen and toxicant, as studied in rats (Gill et al., 2010) and mice (Terrell et al., 2014). The epoxide metabolite of furans, formed in CYP450-mediated oxidations, can isomerize to highly reactive electrophilic intermediates such as cis-2-butene-1,4-dial (Chen et al., 1995; Peterson 2015; Vargas et al., 1998).
We have performed the oxidation of furosemide with m-chloroperbenzoic acid (m-CPBA), and isolated various epoxide and isomerized products in support of our efforts to understand this type of toxicity mechanism, and to also identify potential biomarkers for furosemide in humans. During the separation and drying of the products of the furosemide–m-CPBA reaction, we observed the formation of crystals in the mother liquor (the organic layer). Analysis of these crystals by X-ray crystallography revealed a nonahydrate
of furosemide (starting material) with that of m-chlorobenzoic acid (an inadvertent contaminant or the reduced product of m-CPBA). Analogous to the known properties of co-crystals of furosemide with nicotinamide and their pharmaceutical importance (Aitipamula et al., 2012; Chadha et al., 2012; Goud et al., 2012; Stepanovs & Mishnev, 2012; Ueto et al., 2012), we believe that the co-crystals of furosemide with m-chlorobenzoic acid could have useful applications in drug development and may lead to formulations with improved potency, solubility, and stability. Therefore, this serendipitous finding may have important applications for improving furosemide bioavailability.The 110] direction.
is illustrated in Fig. 1. The furosemide moiety is present as the monoanion, with the COOH group deprotonated, N2 as NH and the primary amine nitrogen N1 as NH2. The m-chlorobenzoate moiety is also deprotonated. Balancing the charge of the two types of anions are two independent sodium cations, both of which are hexacoordinate, with Na···O(water) distances in the range 2.3558 (13)–2.4500 (13) Å. Each Na+ cation is coordinated by three monodentate water molecules, two double-water bridge molecules, and one single-water bridge molecules, as shown in Fig. 2. Thus, centrosymmetric Na2(OH2)8 units are linked by single water bridges, forming chains in the [Hydrogen bonding is extensive (Table 1), with all 21 hydrogen-bond donors involved. Notable features of the two-dimensional hydrogen-bonding pattern (Etter et al.. 1990) are sulfonamide N—H···O bonds to m-chlorobenzoate, secondary amine N—H···O hydrogen bonds to furosemide carboxylate, and water O—H···O hydrogen bonds to sulfonamide O, to both types of carboxylates, and to other water molecules. The direction of the normal to the hydrogen-bonding network is [001]. The furan oxygen atom O5 is not involved in the hydrogen bonding.
Furosemide (8.2 mmol; 2.71 g), dissolved in 3 ml of dichloromethane (DCM), was added dropwise over 5 min to a solution of 8.2 mmol of m-CPBA (1.84 g) and 10.5 mmol NaHCO3 (0.88 g) in 20 ml of DCM on ice with rapid stirring (Fig. 3). After 2 h, an additional 4 mmol of m-CPBA in 10 ml of DCM was added to the reaction mixture. Upon removal from the ice bath, 4 ml of aqueous sodium sulfite solution (10%) was added with stirring for an additional 15 min. After partitioning the layers with deionized water (resistance ~18.2 M Ω cm-1), the organic layer was collected and the aqueous layer was extracted with another 10 ml of DCM. The combined mixture of the organic layer was washed with 10 ml of aqueous solution of NaHCO3 (5%, w/v), dried over anhydrous Na2SO4, and then subjected to partial evaporation under low pressure (ca 4 psi) at 308 K. The partially evaporated sample was left at ambient pressure and temperature overnight. Crystals were formed with slow evaporation.
Crystal data, data collection and structure
details are summarized in Table 2. H atoms on C were idealized with C—H distances of 0.95 Å for sp2 C and 0.99 Å for CH2. Those on N and O were assigned from difference maps, and their positions refined, with O—H distances restrained to be equal. Uiso(H) were assigned as 1.2 times Ueq of the attached atoms (1.5 for water). Six reflections with Fo<<Fc were omitted from the calculations.Data collection: COLLECT (Nonius, 1999); cell
HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The asymmetric unit with 50% ellipsoids. | |
Fig. 2. A portion of the Na–water chain, showing the centrosymmetric Na2(OH2)2 bridges and the single water bridges. | |
Fig. 3. Proposed scheme of reactions of furosemide with m-chloroperoxybenzoic acid. | |
Fig. 4. A supramolecular layer of the title compound in the ab plane. |
[Na2(OH2)9](C7H4ClO2)(C12H10ClN2O5S) | Z = 2 |
Mr = 693.41 | F(000) = 720 |
Triclinic, P1 | Dx = 1.519 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.908 (2) Å | Cell parameters from 17752 reflections |
b = 10.224 (3) Å | θ = 2.5–32.6° |
c = 19.631 (4) Å | µ = 0.39 mm−1 |
α = 85.46 (2)° | T = 100 K |
β = 81.80 (2)° | Lath fragment, colorless |
γ = 74.96 (2)° | 0.30 × 0.25 × 0.07 mm |
V = 1515.7 (7) Å3 |
Nonius KappaCCD diffractometer | 10267 independent reflections |
Radiation source: fine-focus sealed tube | 7760 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.035 |
ω and φ scans | θmax = 32.3°, θmin = 2.7° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.893, Tmax = 0.974 | k = −13→15 |
17752 measured reflections | l = −29→29 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3 |
10267 reflections | (Δ/σ)max = 0.001 |
442 parameters | Δρmax = 0.47 e Å−3 |
120 restraints | Δρmin = −0.55 e Å−3 |
[Na2(OH2)9](C7H4ClO2)(C12H10ClN2O5S) | γ = 74.96 (2)° |
Mr = 693.41 | V = 1515.7 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.908 (2) Å | Mo Kα radiation |
b = 10.224 (3) Å | µ = 0.39 mm−1 |
c = 19.631 (4) Å | T = 100 K |
α = 85.46 (2)° | 0.30 × 0.25 × 0.07 mm |
β = 81.80 (2)° |
Nonius KappaCCD diffractometer | 10267 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 7760 reflections with I > 2s(I) |
Tmin = 0.893, Tmax = 0.974 | Rint = 0.035 |
17752 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 120 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.47 e Å−3 |
10267 reflections | Δρmin = −0.55 e Å−3 |
442 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.62548 (4) | 0.49926 (3) | 0.089838 (16) | 0.01988 (8) | |
S1 | 0.53103 (4) | 0.56412 (3) | 0.252718 (16) | 0.01360 (7) | |
O1 | 0.49898 (12) | 0.54858 (10) | 0.32676 (5) | 0.01772 (19) | |
O2 | 0.61708 (13) | 0.66762 (9) | 0.22345 (5) | 0.0186 (2) | |
O3 | 0.86565 (12) | 0.10830 (9) | 0.36913 (5) | 0.01511 (18) | |
O4 | 0.95416 (13) | −0.04844 (9) | 0.29000 (5) | 0.01778 (19) | |
O5 | 0.92982 (13) | −0.22550 (10) | 0.12326 (6) | 0.0250 (2) | |
N1 | 0.34022 (15) | 0.59988 (12) | 0.22586 (6) | 0.0171 (2) | |
H11N | 0.345 (2) | 0.6226 (18) | 0.1837 (10) | 0.021* | |
H12N | 0.282 (2) | 0.5394 (18) | 0.2404 (9) | 0.021* | |
N2 | 0.97465 (16) | 0.03032 (12) | 0.15946 (6) | 0.0191 (2) | |
H2N | 1.009 (2) | −0.0258 (18) | 0.1927 (9) | 0.023* | |
C1 | 0.65991 (16) | 0.40639 (13) | 0.22332 (6) | 0.0133 (2) | |
C2 | 0.70427 (17) | 0.37919 (13) | 0.15334 (7) | 0.0149 (2) | |
C3 | 0.81105 (18) | 0.25674 (13) | 0.13183 (7) | 0.0165 (2) | |
H3 | 0.8422 | 0.2422 | 0.0840 | 0.020* | |
C4 | 0.87486 (17) | 0.15226 (13) | 0.18053 (7) | 0.0147 (2) | |
C5 | 0.83234 (16) | 0.17957 (12) | 0.25209 (6) | 0.0128 (2) | |
C6 | 0.72692 (16) | 0.30566 (13) | 0.27139 (7) | 0.0131 (2) | |
H6 | 0.6996 | 0.3237 | 0.3190 | 0.016* | |
C7 | 0.88889 (16) | 0.07359 (13) | 0.30778 (7) | 0.0133 (2) | |
C8 | 1.0003 (2) | −0.01178 (14) | 0.08920 (7) | 0.0215 (3) | |
H8A | 1.0944 | 0.0249 | 0.0619 | 0.026* | |
H8B | 0.8900 | 0.0247 | 0.0682 | 0.026* | |
C9 | 1.05072 (18) | −0.16262 (14) | 0.08795 (7) | 0.0179 (3) | |
C10 | 1.19245 (19) | −0.25494 (14) | 0.05907 (7) | 0.0193 (3) | |
H10 | 1.2949 | −0.2372 | 0.0325 | 0.023* | |
C11 | 1.1573 (2) | −0.38525 (14) | 0.07659 (7) | 0.0211 (3) | |
H11 | 1.2312 | −0.4709 | 0.0634 | 0.025* | |
C12 | 0.9991 (2) | −0.36173 (15) | 0.11544 (9) | 0.0252 (3) | |
H12 | 0.9430 | −0.4302 | 0.1348 | 0.030* | |
Cl2 | 0.28737 (6) | 0.23829 (4) | 0.026181 (19) | 0.02904 (9) | |
O6 | 0.15314 (12) | 0.41020 (9) | 0.27976 (5) | 0.01757 (19) | |
O7 | 0.25838 (13) | 0.23500 (10) | 0.35073 (5) | 0.01731 (19) | |
C13 | 0.31680 (17) | 0.20440 (13) | 0.22941 (7) | 0.0147 (2) | |
C14 | 0.27177 (18) | 0.25472 (13) | 0.16425 (7) | 0.0162 (2) | |
H14 | 0.1917 | 0.3408 | 0.1589 | 0.019* | |
C15 | 0.34577 (19) | 0.17705 (14) | 0.10766 (7) | 0.0191 (3) | |
C16 | 0.4648 (2) | 0.05117 (14) | 0.11350 (8) | 0.0230 (3) | |
H16 | 0.5148 | −0.0002 | 0.0740 | 0.028* | |
C17 | 0.5091 (2) | 0.00209 (15) | 0.17849 (8) | 0.0243 (3) | |
H17 | 0.5903 | −0.0836 | 0.1836 | 0.029* | |
C18 | 0.43507 (18) | 0.07803 (14) | 0.23614 (7) | 0.0198 (3) | |
H18 | 0.4654 | 0.0434 | 0.2804 | 0.024* | |
C19 | 0.23698 (16) | 0.28915 (13) | 0.29148 (7) | 0.0140 (2) | |
Na1 | 0.01996 (6) | 0.65083 (5) | 0.45870 (3) | 0.01372 (11) | |
Na2 | −0.44798 (7) | 0.87445 (5) | 0.44265 (3) | 0.01394 (11) | |
O8 | −0.15551 (12) | 0.88218 (10) | 0.46379 (5) | 0.01546 (18) | |
H81 | −0.126 (2) | 0.9400 (19) | 0.4362 (10) | 0.023* | |
H82 | −0.175 (2) | 0.9155 (18) | 0.5017 (10) | 0.023* | |
O9 | 0.19980 (12) | 0.42119 (10) | 0.45986 (5) | 0.01525 (18) | |
H91 | 0.295 (2) | 0.4001 (18) | 0.4793 (9) | 0.023* | |
H92 | 0.217 (2) | 0.3797 (19) | 0.4253 (10) | 0.023* | |
O10 | 0.18912 (12) | 0.66647 (10) | 0.54828 (5) | 0.01560 (18) | |
H101 | 0.169 (2) | 0.6053 (19) | 0.5718 (10) | 0.023* | |
H102 | 0.158 (2) | 0.7401 (18) | 0.5767 (9) | 0.023* | |
O11 | −0.10007 (13) | 0.54861 (10) | 0.37594 (5) | 0.01550 (18) | |
H111 | −0.026 (2) | 0.5051 (18) | 0.3452 (10) | 0.023* | |
H112 | −0.161 (2) | 0.6123 (19) | 0.3560 (9) | 0.023* | |
O12 | −0.30234 (14) | 0.80747 (10) | 0.33026 (5) | 0.0182 (2) | |
H121 | −0.221 (2) | 0.8455 (19) | 0.3142 (10) | 0.027* | |
H122 | −0.329 (2) | 0.7843 (19) | 0.2985 (10) | 0.027* | |
O13 | −0.47562 (13) | 1.11930 (10) | 0.43409 (5) | 0.01560 (18) | |
H131 | −0.543 (2) | 1.1568 (19) | 0.4070 (10) | 0.023* | |
H132 | −0.380 (2) | 1.1303 (18) | 0.4114 (10) | 0.023* | |
O14 | 0.16422 (13) | 0.76011 (10) | 0.36697 (5) | 0.01745 (19) | |
H141 | 0.108 (3) | 0.802 (2) | 0.3408 (10) | 0.026* | |
H142 | 0.236 (3) | 0.713 (2) | 0.3462 (10) | 0.026* | |
O15 | −0.73738 (13) | 0.97411 (10) | 0.41518 (5) | 0.01661 (19) | |
H151 | −0.770 (2) | 0.9090 (19) | 0.4010 (9) | 0.025* | |
H152 | −0.753 (2) | 1.0342 (19) | 0.3861 (10) | 0.025* | |
O16 | −0.49332 (13) | 0.65364 (10) | 0.46360 (5) | 0.01549 (18) | |
H161 | −0.582 (2) | 0.6532 (18) | 0.4885 (10) | 0.023* | |
H162 | −0.494 (2) | 0.6123 (18) | 0.4305 (10) | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02539 (17) | 0.01556 (15) | 0.01459 (14) | 0.00207 (12) | −0.00343 (12) | 0.00125 (11) |
S1 | 0.01423 (14) | 0.01061 (14) | 0.01548 (15) | −0.00184 (11) | −0.00167 (11) | −0.00254 (11) |
O1 | 0.0191 (5) | 0.0175 (5) | 0.0155 (4) | −0.0020 (4) | −0.0016 (4) | −0.0041 (4) |
O2 | 0.0209 (5) | 0.0136 (4) | 0.0221 (5) | −0.0062 (4) | −0.0016 (4) | −0.0022 (4) |
O3 | 0.0167 (4) | 0.0147 (4) | 0.0138 (4) | −0.0036 (4) | −0.0024 (3) | −0.0002 (3) |
O4 | 0.0240 (5) | 0.0108 (4) | 0.0176 (5) | −0.0022 (4) | −0.0036 (4) | −0.0001 (3) |
O5 | 0.0199 (5) | 0.0182 (5) | 0.0335 (6) | −0.0016 (4) | 0.0032 (4) | −0.0038 (4) |
N1 | 0.0153 (5) | 0.0159 (5) | 0.0194 (6) | −0.0022 (4) | −0.0036 (4) | 0.0003 (4) |
N2 | 0.0276 (6) | 0.0118 (5) | 0.0141 (5) | 0.0027 (5) | −0.0032 (5) | −0.0016 (4) |
C1 | 0.0137 (5) | 0.0117 (6) | 0.0144 (6) | −0.0022 (4) | −0.0020 (4) | −0.0027 (4) |
C2 | 0.0170 (6) | 0.0129 (6) | 0.0146 (6) | −0.0027 (5) | −0.0039 (5) | 0.0015 (4) |
C3 | 0.0207 (6) | 0.0137 (6) | 0.0134 (6) | −0.0014 (5) | −0.0019 (5) | −0.0013 (4) |
C4 | 0.0158 (6) | 0.0120 (6) | 0.0155 (6) | −0.0018 (5) | −0.0019 (5) | −0.0021 (4) |
C5 | 0.0138 (5) | 0.0108 (5) | 0.0141 (6) | −0.0035 (5) | −0.0022 (4) | −0.0006 (4) |
C6 | 0.0129 (5) | 0.0128 (6) | 0.0147 (6) | −0.0044 (5) | −0.0023 (4) | −0.0019 (4) |
C7 | 0.0118 (5) | 0.0137 (6) | 0.0155 (6) | −0.0050 (5) | −0.0019 (4) | 0.0002 (4) |
C8 | 0.0317 (8) | 0.0147 (6) | 0.0144 (6) | 0.0003 (6) | −0.0010 (5) | −0.0025 (5) |
C9 | 0.0205 (6) | 0.0153 (6) | 0.0169 (6) | −0.0024 (5) | −0.0022 (5) | −0.0028 (5) |
C10 | 0.0205 (6) | 0.0173 (6) | 0.0179 (6) | −0.0011 (5) | −0.0019 (5) | −0.0015 (5) |
C11 | 0.0266 (7) | 0.0137 (6) | 0.0210 (7) | 0.0011 (5) | −0.0064 (5) | −0.0033 (5) |
C12 | 0.0252 (7) | 0.0158 (7) | 0.0351 (8) | −0.0059 (6) | −0.0027 (6) | −0.0037 (6) |
Cl2 | 0.0479 (2) | 0.02199 (18) | 0.01606 (16) | −0.00506 (16) | −0.00745 (15) | −0.00001 (13) |
O6 | 0.0176 (4) | 0.0127 (4) | 0.0196 (5) | 0.0003 (4) | −0.0008 (4) | −0.0010 (4) |
O7 | 0.0203 (5) | 0.0165 (5) | 0.0149 (4) | −0.0031 (4) | −0.0048 (4) | −0.0003 (3) |
C13 | 0.0144 (6) | 0.0130 (6) | 0.0168 (6) | −0.0029 (5) | −0.0032 (5) | −0.0016 (4) |
C14 | 0.0187 (6) | 0.0114 (6) | 0.0182 (6) | −0.0026 (5) | −0.0038 (5) | 0.0002 (5) |
C15 | 0.0268 (7) | 0.0167 (6) | 0.0146 (6) | −0.0067 (5) | −0.0036 (5) | 0.0006 (5) |
C16 | 0.0299 (7) | 0.0166 (7) | 0.0204 (7) | −0.0033 (6) | 0.0017 (6) | −0.0047 (5) |
C17 | 0.0282 (7) | 0.0137 (6) | 0.0257 (7) | 0.0036 (6) | −0.0017 (6) | −0.0020 (5) |
C18 | 0.0217 (7) | 0.0156 (6) | 0.0192 (6) | 0.0000 (5) | −0.0031 (5) | 0.0012 (5) |
C19 | 0.0119 (5) | 0.0137 (6) | 0.0170 (6) | −0.0037 (5) | −0.0039 (4) | −0.0002 (4) |
Na1 | 0.0119 (2) | 0.0117 (2) | 0.0173 (3) | −0.00179 (19) | −0.00343 (19) | −0.00038 (19) |
Na2 | 0.0129 (2) | 0.0116 (2) | 0.0173 (3) | −0.00220 (19) | −0.00328 (19) | −0.00089 (19) |
O8 | 0.0164 (4) | 0.0126 (4) | 0.0164 (5) | −0.0017 (4) | −0.0026 (4) | −0.0003 (4) |
O9 | 0.0129 (4) | 0.0153 (4) | 0.0168 (5) | −0.0006 (4) | −0.0040 (4) | −0.0025 (3) |
O10 | 0.0168 (4) | 0.0128 (4) | 0.0182 (5) | −0.0054 (4) | −0.0022 (4) | −0.0011 (4) |
O11 | 0.0138 (4) | 0.0139 (4) | 0.0173 (5) | −0.0006 (4) | −0.0022 (4) | −0.0006 (4) |
O12 | 0.0196 (5) | 0.0178 (5) | 0.0187 (5) | −0.0063 (4) | −0.0044 (4) | −0.0014 (4) |
O13 | 0.0127 (4) | 0.0158 (5) | 0.0181 (5) | −0.0030 (4) | −0.0036 (4) | 0.0012 (4) |
O14 | 0.0142 (5) | 0.0155 (5) | 0.0207 (5) | −0.0006 (4) | −0.0008 (4) | −0.0025 (4) |
O15 | 0.0168 (5) | 0.0142 (5) | 0.0205 (5) | −0.0047 (4) | −0.0065 (4) | −0.0005 (4) |
O16 | 0.0138 (4) | 0.0150 (5) | 0.0184 (5) | −0.0041 (4) | −0.0020 (4) | −0.0031 (4) |
Cl1—C2 | 1.7411 (14) | C14—H14 | 0.9500 |
S1—O2 | 1.4418 (10) | C15—C16 | 1.391 (2) |
S1—O1 | 1.4427 (10) | C16—C17 | 1.392 (2) |
S1—N1 | 1.6120 (13) | C16—H16 | 0.9500 |
S1—C1 | 1.7604 (14) | C17—C18 | 1.393 (2) |
O3—C7 | 1.2572 (16) | C17—H17 | 0.9500 |
O4—C7 | 1.2761 (16) | C18—H18 | 0.9500 |
O5—C9 | 1.3664 (17) | Na1—O14 | 2.3558 (13) |
O5—C12 | 1.3703 (18) | Na1—O10 | 2.3946 (12) |
N1—H11N | 0.839 (18) | Na1—O9i | 2.4090 (12) |
N1—H12N | 0.872 (18) | Na1—O9 | 2.4091 (13) |
N2—C4 | 1.3512 (17) | Na1—O8 | 2.4134 (13) |
N2—C8 | 1.4483 (18) | Na1—O11 | 2.4200 (12) |
N2—H2N | 0.860 (18) | Na2—O15 | 2.3709 (13) |
C1—C6 | 1.3919 (18) | Na2—O16 | 2.3718 (13) |
C1—C2 | 1.4001 (18) | Na2—O12 | 2.4016 (13) |
C2—C3 | 1.3755 (19) | Na2—O13ii | 2.4108 (12) |
C3—C4 | 1.4163 (18) | Na2—O8 | 2.4294 (12) |
C3—H3 | 0.9500 | Na2—O13 | 2.4500 (13) |
C4—C5 | 1.4295 (18) | O8—H81 | 0.83 (2) |
C5—C6 | 1.3892 (18) | O8—H82 | 0.821 (19) |
C5—C7 | 1.5066 (18) | O9—Na1i | 2.4090 (12) |
C6—H6 | 0.9500 | O9—H91 | 0.862 (19) |
C8—C9 | 1.4907 (19) | O9—H92 | 0.806 (19) |
C8—H8A | 0.9900 | O10—H101 | 0.784 (19) |
C8—H8B | 0.9900 | O10—H102 | 0.932 (18) |
C9—C10 | 1.3501 (19) | O11—H111 | 0.842 (19) |
C10—C11 | 1.436 (2) | O11—H112 | 0.811 (19) |
C10—H10 | 0.9500 | O12—H121 | 0.848 (19) |
C11—C12 | 1.344 (2) | O12—H122 | 0.76 (2) |
C11—H11 | 0.9500 | O13—Na2ii | 2.4108 (12) |
C12—H12 | 0.9500 | O13—H131 | 0.807 (19) |
Cl2—C15 | 1.7510 (15) | O13—H132 | 0.848 (19) |
O6—C19 | 1.2637 (16) | O14—H141 | 0.76 (2) |
O7—C19 | 1.2623 (16) | O14—H142 | 0.74 (2) |
C13—C18 | 1.3938 (19) | O15—H151 | 0.853 (19) |
C13—C14 | 1.3995 (18) | O15—H152 | 0.803 (19) |
C13—C19 | 1.5158 (19) | O16—H161 | 0.798 (19) |
C14—C15 | 1.3857 (19) | O16—H162 | 0.80 (2) |
O2—S1—O1 | 118.19 (6) | O7—C19—O6 | 124.65 (13) |
O2—S1—N1 | 106.89 (7) | O7—C19—C13 | 118.41 (12) |
O1—S1—N1 | 106.20 (7) | O6—C19—C13 | 116.94 (12) |
O2—S1—C1 | 108.39 (6) | O14—Na1—O10 | 99.71 (4) |
O1—S1—C1 | 106.54 (6) | O14—Na1—O9i | 163.93 (4) |
N1—S1—C1 | 110.57 (6) | O10—Na1—O9i | 91.71 (4) |
C9—O5—C12 | 106.30 (11) | O14—Na1—O9 | 103.75 (5) |
S1—N1—H11N | 112.4 (11) | O10—Na1—O9 | 81.57 (4) |
S1—N1—H12N | 112.1 (11) | O9i—Na1—O9 | 89.00 (4) |
H11N—N1—H12N | 116.8 (16) | O14—Na1—O8 | 77.59 (4) |
C4—N2—C8 | 124.07 (12) | O10—Na1—O8 | 95.33 (4) |
C4—N2—H2N | 113.6 (12) | O9i—Na1—O8 | 90.19 (4) |
C8—N2—H2N | 121.6 (12) | O9—Na1—O8 | 176.78 (4) |
C6—C1—C2 | 118.22 (12) | O14—Na1—O11 | 89.24 (4) |
C6—C1—S1 | 118.85 (10) | O10—Na1—O11 | 159.01 (4) |
C2—C1—S1 | 122.88 (10) | O9i—Na1—O11 | 83.87 (4) |
C3—C2—C1 | 121.58 (12) | O9—Na1—O11 | 77.85 (4) |
C3—C2—Cl1 | 117.22 (10) | O8—Na1—O11 | 105.17 (4) |
C1—C2—Cl1 | 121.21 (10) | O15—Na2—O16 | 94.41 (4) |
C2—C3—C4 | 120.46 (12) | O15—Na2—O12 | 99.60 (4) |
C2—C3—H3 | 119.8 | O16—Na2—O12 | 88.32 (4) |
C4—C3—H3 | 119.8 | O15—Na2—O13ii | 96.08 (4) |
N2—C4—C3 | 120.49 (12) | O16—Na2—O13ii | 81.69 (4) |
N2—C4—C5 | 121.12 (12) | O12—Na2—O13ii | 162.00 (4) |
C3—C4—C5 | 118.38 (12) | O15—Na2—O8 | 153.51 (4) |
C6—C5—C4 | 119.11 (12) | O16—Na2—O8 | 111.98 (4) |
C6—C5—C7 | 118.49 (11) | O12—Na2—O8 | 83.99 (4) |
C4—C5—C7 | 122.30 (11) | O13ii—Na2—O8 | 85.91 (4) |
C5—C6—C1 | 122.19 (12) | O15—Na2—O13 | 74.54 (4) |
C5—C6—H6 | 118.9 | O16—Na2—O13 | 166.06 (4) |
C1—C6—H6 | 118.9 | O12—Na2—O13 | 101.72 (4) |
O3—C7—O4 | 123.35 (12) | O13ii—Na2—O13 | 90.90 (4) |
O3—C7—C5 | 119.00 (11) | O8—Na2—O13 | 79.02 (4) |
O4—C7—C5 | 117.62 (11) | Na1—O8—Na2 | 105.44 (4) |
N2—C8—C9 | 110.13 (12) | Na1—O8—H81 | 118.9 (13) |
N2—C8—H8A | 109.6 | Na2—O8—H81 | 106.7 (12) |
C9—C8—H8A | 109.6 | Na1—O8—H82 | 116.0 (13) |
N2—C8—H8B | 109.6 | Na2—O8—H82 | 102.7 (12) |
C9—C8—H8B | 109.6 | H81—O8—H82 | 105.7 (17) |
H8A—C8—H8B | 108.1 | Na1i—O9—Na1 | 91.00 (4) |
C10—C9—O5 | 110.48 (12) | Na1i—O9—H91 | 105.6 (12) |
C10—C9—C8 | 134.27 (13) | Na1—O9—H91 | 120.6 (12) |
O5—C9—C8 | 115.26 (12) | Na1i—O9—H92 | 109.7 (13) |
C9—C10—C11 | 106.27 (13) | Na1—O9—H92 | 118.4 (13) |
C9—C10—H10 | 126.9 | H91—O9—H92 | 108.7 (17) |
C11—C10—H10 | 126.9 | Na1—O10—H101 | 97.5 (13) |
C12—C11—C10 | 106.22 (13) | Na1—O10—H102 | 122.0 (11) |
C12—C11—H11 | 126.9 | H101—O10—H102 | 105.4 (17) |
C10—C11—H11 | 126.9 | Na1—O11—H111 | 116.0 (11) |
C11—C12—O5 | 110.72 (13) | Na1—O11—H112 | 104.5 (13) |
C11—C12—H12 | 124.6 | H111—O11—H112 | 105.9 (17) |
O5—C12—H12 | 124.6 | Na2—O12—H121 | 115.2 (13) |
C18—C13—C14 | 119.61 (13) | Na2—O12—H122 | 135.5 (14) |
C18—C13—C19 | 121.12 (12) | H121—O12—H122 | 103.8 (19) |
C14—C13—C19 | 119.27 (12) | Na2ii—O13—Na2 | 89.10 (4) |
C15—C14—C13 | 119.01 (12) | Na2ii—O13—H131 | 123.6 (13) |
C15—C14—H14 | 120.5 | Na2—O13—H131 | 111.3 (13) |
C13—C14—H14 | 120.5 | Na2ii—O13—H132 | 126.5 (12) |
C14—C15—C16 | 122.04 (13) | Na2—O13—H132 | 106.2 (12) |
C14—C15—Cl2 | 119.23 (11) | H131—O13—H132 | 98.4 (17) |
C16—C15—Cl2 | 118.73 (11) | Na1—O14—H141 | 117.4 (14) |
C15—C16—C17 | 118.54 (14) | Na1—O14—H142 | 113.1 (15) |
C15—C16—H16 | 120.7 | H141—O14—H142 | 104 (2) |
C17—C16—H16 | 120.7 | Na2—O15—H151 | 104.6 (12) |
C16—C17—C18 | 120.34 (13) | Na2—O15—H152 | 119.8 (13) |
C16—C17—H17 | 119.8 | H151—O15—H152 | 106.5 (18) |
C18—C17—H17 | 119.8 | Na2—O16—H161 | 112.4 (13) |
C17—C18—C13 | 120.46 (13) | Na2—O16—H162 | 117.0 (13) |
C17—C18—H18 | 119.8 | H161—O16—H162 | 106.8 (18) |
C13—C18—H18 | 119.8 | ||
O2—S1—C1—C6 | 119.77 (10) | C10—C11—C12—O5 | 0.73 (17) |
O1—S1—C1—C6 | −8.40 (12) | C9—O5—C12—C11 | −0.22 (17) |
N1—S1—C1—C6 | −123.38 (11) | C18—C13—C14—C15 | 0.23 (19) |
O2—S1—C1—C2 | −57.59 (12) | C19—C13—C14—C15 | 179.71 (12) |
O1—S1—C1—C2 | 174.23 (10) | C13—C14—C15—C16 | −0.7 (2) |
N1—S1—C1—C2 | 59.26 (13) | C13—C14—C15—Cl2 | 179.03 (10) |
C6—C1—C2—C3 | −0.01 (19) | C14—C15—C16—C17 | 0.5 (2) |
S1—C1—C2—C3 | 177.37 (10) | Cl2—C15—C16—C17 | −179.18 (12) |
C6—C1—C2—Cl1 | 179.75 (10) | C15—C16—C17—C18 | 0.1 (2) |
S1—C1—C2—Cl1 | −2.87 (16) | C16—C17—C18—C13 | −0.5 (2) |
C1—C2—C3—C4 | 2.1 (2) | C14—C13—C18—C17 | 0.3 (2) |
Cl1—C2—C3—C4 | −177.66 (10) | C19—C13—C18—C17 | −179.15 (13) |
C8—N2—C4—C3 | −10.5 (2) | C18—C13—C19—O7 | −10.56 (19) |
C8—N2—C4—C5 | 170.04 (13) | C14—C13—C19—O7 | 169.97 (11) |
C2—C3—C4—N2 | 177.67 (12) | C18—C13—C19—O6 | 169.39 (12) |
C2—C3—C4—C5 | −2.87 (19) | C14—C13—C19—O6 | −10.09 (18) |
N2—C4—C5—C6 | −178.95 (12) | O14—Na1—O8—Na2 | 117.64 (5) |
C3—C4—C5—C6 | 1.59 (18) | O10—Na1—O8—Na2 | −143.56 (4) |
N2—C4—C5—C7 | −2.64 (19) | O9i—Na1—O8—Na2 | −51.83 (5) |
C3—C4—C5—C7 | 177.90 (11) | O11—Na1—O8—Na2 | 31.87 (5) |
C4—C5—C6—C1 | 0.48 (19) | Na1i—Na1—O8—Na2 | −54.90 (7) |
C7—C5—C6—C1 | −175.97 (11) | O15—Na2—O8—Na1 | −165.17 (8) |
C2—C1—C6—C5 | −1.29 (18) | O16—Na2—O8—Na1 | 20.07 (6) |
S1—C1—C6—C5 | −178.78 (10) | O12—Na2—O8—Na1 | −65.67 (5) |
C6—C5—C7—O3 | −12.06 (17) | O13ii—Na2—O8—Na1 | 99.40 (5) |
C4—C5—C7—O3 | 171.61 (11) | O13—Na2—O8—Na1 | −168.88 (5) |
C6—C5—C7—O4 | 166.10 (11) | Na2ii—Na2—O8—Na1 | 145.27 (4) |
C4—C5—C7—O4 | −10.23 (18) | O14—Na1—O9—Na1i | −170.12 (4) |
C4—N2—C8—C9 | −156.88 (13) | O10—Na1—O9—Na1i | 91.87 (4) |
C12—O5—C9—C10 | −0.43 (16) | O9i—Na1—O9—Na1i | 0.0 |
C12—O5—C9—C8 | 179.48 (12) | O11—Na1—O9—Na1i | −83.94 (4) |
N2—C8—C9—C10 | −119.97 (17) | O15—Na2—O13—Na2ii | 96.06 (4) |
N2—C8—C9—O5 | 60.15 (16) | O16—Na2—O13—Na2ii | 57.56 (17) |
O5—C9—C10—C11 | 0.86 (16) | O12—Na2—O13—Na2ii | −167.08 (4) |
C8—C9—C10—C11 | −179.02 (15) | O13ii—Na2—O13—Na2ii | 0.0 |
C9—C10—C11—C12 | −0.96 (16) | O8—Na2—O13—Na2ii | −85.65 (4) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11N···Cl1 | 0.839 (18) | 2.767 (17) | 3.2848 (16) | 121.6 (14) |
N1—H12N···O6 | 0.872 (18) | 1.920 (18) | 2.7905 (17) | 175.3 (17) |
N2—H2N···O4 | 0.860 (18) | 1.906 (18) | 2.6199 (16) | 139.4 (16) |
O8—H81···O3iii | 0.83 (2) | 2.07 (2) | 2.8737 (16) | 162 (2) |
O8—H82···O15ii | 0.82 (2) | 2.00 (2) | 2.8025 (16) | 168 (2) |
O9—H91···O16i | 0.86 (2) | 1.99 (2) | 2.8499 (15) | 172 (2) |
O9—H92···O7 | 0.81 (2) | 2.10 (2) | 2.8867 (16) | 167 (2) |
O10—H101···O11i | 0.78 (2) | 1.96 (2) | 2.7444 (16) | 174 (2) |
O10—H102···O3iv | 0.93 (2) | 1.90 (2) | 2.8271 (15) | 171 (2) |
O11—H111···O6 | 0.84 (2) | 1.89 (2) | 2.7296 (16) | 176 (2) |
O11—H112···O12 | 0.81 (2) | 2.08 (2) | 2.8641 (16) | 162 (2) |
O12—H121···O4iii | 0.85 (2) | 1.96 (2) | 2.7962 (16) | 171 (2) |
O12—H122···O2v | 0.76 (2) | 2.12 (2) | 2.8593 (15) | 165 (2) |
O13—H131···O7iii | 0.81 (2) | 2.01 (2) | 2.8082 (15) | 169 (2) |
O13—H132···O3iii | 0.85 (2) | 1.97 (2) | 2.7939 (15) | 165 (2) |
O14—H141···O4iii | 0.76 (2) | 1.99 (2) | 2.7265 (16) | 164 (2) |
O14—H142···O1 | 0.74 (2) | 2.31 (2) | 3.0019 (17) | 156 (2) |
O15—H151···O14v | 0.85 (2) | 1.92 (2) | 2.7766 (16) | 178 (2) |
O15—H152···O7iii | 0.80 (2) | 2.14 (2) | 2.8545 (16) | 149 (2) |
O16—H161···O10v | 0.798 (19) | 1.990 (19) | 2.7857 (16) | 175.7 (18) |
O16—H162···O1v | 0.80 (2) | 2.20 (2) | 2.9852 (15) | 165.8 (17) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y+2, −z+1; (iii) x−1, y+1, z; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11N···Cl1 | 0.839 (18) | 2.767 (17) | 3.2848 (16) | 121.6 (14) |
N1—H12N···O6 | 0.872 (18) | 1.920 (18) | 2.7905 (17) | 175.3 (17) |
N2—H2N···O4 | 0.860 (18) | 1.906 (18) | 2.6199 (16) | 139.4 (16) |
O8—H81···O3i | 0.83 (2) | 2.07 (2) | 2.8737 (16) | 162.4 (17) |
O8—H82···O15ii | 0.821 (19) | 1.995 (19) | 2.8025 (16) | 167.6 (17) |
O9—H91···O16iii | 0.862 (19) | 1.994 (19) | 2.8499 (15) | 171.8 (17) |
O9—H92···O7 | 0.806 (19) | 2.10 (2) | 2.8867 (16) | 167.3 (18) |
O10—H101···O11iii | 0.784 (19) | 1.964 (19) | 2.7444 (16) | 173.7 (18) |
O10—H102···O3iv | 0.932 (18) | 1.903 (18) | 2.8271 (15) | 170.6 (15) |
O11—H111···O6 | 0.842 (19) | 1.889 (19) | 2.7296 (16) | 175.6 (16) |
O11—H112···O12 | 0.811 (19) | 2.082 (19) | 2.8641 (16) | 161.9 (17) |
O12—H121···O4i | 0.848 (19) | 1.96 (2) | 2.7962 (16) | 170.8 (18) |
O12—H122···O2v | 0.76 (2) | 2.12 (2) | 2.8593 (15) | 165 (2) |
O13—H131···O7i | 0.807 (19) | 2.011 (19) | 2.8082 (15) | 169.4 (18) |
O13—H132···O3i | 0.848 (19) | 1.966 (19) | 2.7939 (15) | 165.0 (17) |
O14—H141···O4i | 0.76 (2) | 1.99 (2) | 2.7265 (16) | 164 (2) |
O14—H142···O1 | 0.74 (2) | 2.31 (2) | 3.0019 (17) | 155.7 (19) |
O15—H151···O14v | 0.853 (19) | 1.92 (2) | 2.7766 (16) | 177.8 (18) |
O15—H152···O7i | 0.803 (19) | 2.135 (19) | 2.8545 (16) | 149.2 (17) |
O16—H161···O10v | 0.798 (19) | 1.990 (19) | 2.7857 (16) | 175.7 (18) |
O16—H162···O1v | 0.80 (2) | 2.20 (2) | 2.9852 (15) | 165.8 (17) |
Symmetry codes: (i) x−1, y+1, z; (ii) −x−1, −y+2, −z+1; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Na2(OH2)9](C7H4ClO2)(C12H10ClN2O5S) |
Mr | 693.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.908 (2), 10.224 (3), 19.631 (4) |
α, β, γ (°) | 85.46 (2), 81.80 (2), 74.96 (2) |
V (Å3) | 1515.7 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.30 × 0.25 × 0.07 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.893, 0.974 |
No. of measured, independent and observed [I > 2s(I)] reflections | 17752, 10267, 7760 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.751 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.107, 1.05 |
No. of reflections | 10267 |
No. of parameters | 442 |
No. of restraints | 120 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.55 |
Computer programs: COLLECT (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).
Acknowledgements
The research presented within was made possible by funding from the National Science Foundation (NSF) ACE Implementation (HRD-1043316) and CAREER (CHE-1230357) programs, and the US Department of Education (DoE) grant PO31B040030 (Title III, Part B - Strengthening Historically Black Graduate Institutions). The contents of this publication are solely the responsibility of the authors and do not necessarily represent the official views of the NSF or US DoE. The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.
References
Aitipamula, S., et al. (2012). Cryst. Growth Des. 12, 2147–2152. Web of Science CrossRef CAS Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340. Web of Science CrossRef CAS IUCr Journals Google Scholar
Belen, B., Oguz, A., Okur, A. & Dalgic, B. (2014). BMJ Case Rep. pii: bcr2014203746. doi: 10.1136/bcr-2014-203746. Google Scholar
Carvalhana, V., Burry, L. & Lapinsky, S. E. (2006). J. Crit. Care, 21, 316–321. CrossRef PubMed Google Scholar
Chadha, R., Saini, A., Arora, P. & Bhandari, S. (2012). Crit. Rev. Ther. Drug Carrier Syst. 29, 183–218. CrossRef CAS PubMed Google Scholar
Chen, L. J., Hecht, S. S. & Peterson, L. A. (1995). Chem. Res. Toxicol. 8, 903–906. CrossRef CAS PubMed Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gill, S., Bondy, G., Lefebvre, D. E., Becalski, A., Kavanagh, M., Hou, Y., Turcotte, A. M., Barker, M., Weld, M., Vavasour, E. & Cooke, G. M. (2010). Toxicol. Pathol. 38, 619–630. CrossRef CAS PubMed Google Scholar
Goud, N. R., Gangavaram, S., Suresh, K., Pal, S., Manjunatha, S. G., Nambiar, S. & Nangia, A. (2012). J. Pharm. Sci. 101, 664–680. CrossRef CAS PubMed Google Scholar
Krumlovsky, F. A. & del Greco, F. (1976). Postgrad. Med. 59, 105–110. PubMed CAS Google Scholar
Musini, V. M., Rezapour, P., Wright, J. M., Bassett, K. & Jauca, C. D. (2015). Cochrane Database Syst. Rev. 8, CD003825. doi: 10.1002/14651858.CD003825.pub3. Google Scholar
Nonius (1999). KappaCCD Software. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Peterson, L. A. (2015). Drug Metab. Rev. 38, 615–626. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stepanovs, D. & Mishnev, A. (2012). Acta Cryst. C68, o488–o491. CrossRef IUCr Journals Google Scholar
Terrell, A. N., Huynh, M., Grill, A. E., Kovi, R. C., O'Sullivan, M. G., Guttenplan, J. B., Ho, Y. Y. & Peterson, L. A. (2014). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 770, 46–54. CrossRef CAS PubMed Google Scholar
Ueto, T., Takata, N., Muroyama, N., Nedu, A., Sasaki, A., Tanida, S. & Terada, K. (2012). Cryst. Growth Des. 12, 485–494. Web of Science CSD CrossRef CAS Google Scholar
Vargas, F., Martinez Volkmar, I., Sequera, J., Mendez, H., Rojas, J., Fraile, G., Velasquez, M. & Medina, R. (1998). J. Photochem. Photobiol. B, 42, 219–225. CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.