research communications
Poly[μ2-aqua-aqua[μ3-N-butyl-N-(2-hydroxyethyl)dithiocarbamato-κ3O,O′:S]sodium]
aSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand
*Correspondence e-mail: rbutcher99@yahoo.com
In the title compound, [Na(C7H14NOS2)(H2O)2]n, the NaI cation is coordinated by five O atoms [Na—O = 2.3142 (11)–2.4677 (10) Å] from three aqua and two N-butyl-N-(2-hydroxyethyl)dithiocarbamate (L) ligands and one S atom [Na—S = 3.0074 (6) Å] from a third L ligand in a highly distorted octahedral geometry. Two aqua ligands related by an inversion center bridge two NaI cations, and each L ligand coordinates three NaI cations, leading to a layered arrangement aligned parallel to the bc plane. Intermolecular O—H⋯S hydrogen bonds are observed in the inner part of each polymeric layer; these are packed along the a axis and held together by weak van der Waals forces.
CCDC reference: 1447132
1. Chemical context
Dithiocarbamates have recently drawn more attention due to their application in group-transfer radical ) and as ligands for chelating metals (Greenwood & Earnshaw, 1997). In recent years, their applications have not only become apparent as pesticides and fungicides, but they have also been widely used as vulcanization accelerators in the rubber industry (Svetlik et al., 1955). Dithiocarbamates are also of biological importance due to their anticancer, antibacterial, antituberculosis and antifungal properties (Li et al., 2015; Sim et al., 2014; Chauhan et al., 2012; Byrne et al., 2007). Their anti-oxidant properties make them even more valuable compounds. As part of our investigations on organotindithio complexes (Srivastava et al., 2007), we herein report the synthesis and structure of the title compound.
reactions (Grainger & Innocenti, 20072. Structural commentary
The title compound is a two-dimensional polymer with formula [Na(μ3-C7H14NOS2)(μ2-H2O)(H2O)]. Within this polymer, each NaI ion exhibits a distorted octahedral geometry (Fig. 1) made up from coordination by the S atom of one N-butyl-N-(2-hydroxyethyl)dithiocarbamate (L) anion, two hydroxy O atoms from two L ligands and three aqua ligands, of which two aqua ligands form bridging units between two NaI cations. The dithiocarbamate anion acts as a triply bridging ligand, where one S atom coordinates one sodium atom and the Ohydroxy atom coordinates two sodium atoms (Fig. 2). The aforementioned feature of multiple coordination modes leads to the formation of polymeric layers parallel to the bc plane with the hydrophobic butyl arms protruding up and down. In the L ligand, while the two S atoms are not chemically equivalent as only one is involved in bonding to the Na cation, the C—S bond lengths are identical at 1.726 (1) Å.
3. Supramolecular features
Intermolecular O—H⋯S hydrogen bonds (Table 1) are observed in the inner part of each polymeric layer (Fig. 3). The layers are further packed along the a axis and held together by weak van der Waals forces.
4. Database survey
In a recent publication, Howie et al. (2008) reported a structurally similar compound where the butyl substituent was replaced by a propyl substituent. The crystal structures of other sodium salts of dithiocarbamates, Na[S2CN(C2H5)2]·3H2O (Colapietro et al., 1968), Na[S2CN(CH2)4]·2H2O (Albertsson et al., 1980; Ymén, 1982), Na[S2CN(C3H7)2]·5H2O (Ymén, 1983) and Na[S2CN(CH3)2]·2H2O (Oskarsson & Ymén, 1983), Na[S2CN(CH2)5]·2H2O (Mafud & Gambardella, 2011), Na[S2CN(C8H5NS)]·3H2O (Téllez et al., 2004) have been reported. All these structures are polymeric in nature and contain the μ(H2O)2Na2 unit.
5. Synthesis and crystallization
The title compound was prepared by the reaction of N-butyl N-hydroxyethyl amine (0.01 mol), carbon disulfide (0.01 mol) and sodium hydroxide (0.01 mol) in dry diethyl ether and was stirred for 4 h at 253 K. The crude product was recrystallized from isopropyl alcohol. It was then dissolved in a hexane:diethyl ether (1:1 v/v) mixture and put in a deep freezer overnight. Square transparent crystals suitable for X ray analysis were obtained in 80% yield (m.p.: 430 K). Analysis calculated for C7H18NO3S2 (%) S, 29.78; found: S, 29.84.
6. Refinement
Crystal data, data collection and structure . All C-bound H atoms were idealized with C—H distances of 0.99 Å for CH2 and 0.98 Å for CH3 groups with atomic displacement parameters of Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The water and hydroxyl H atoms were freely refined.
details are summarized in Table 2Supporting information
CCDC reference: 1447132
10.1107/S2056989016000657/cv5500sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016000657/cv5500Isup2.hkl
Dithiocarbamates have recently drawn more attention due to their application in group-transfer radical
reactions (Grainger & Innocenti, 2007) and as ligands for chelating metals (Greenwood & Earnshaw, 1997). In recent years, their applications have not only become apparent as pesticides and fungicides, but they have also been widely used as vulcanization accelerators in the rubber industry (Svetlik et al., 1955). Dithiocarbamates are also of biological importance due to their anticancer, antibacterial, antituberculosis and antifungal properties (Li et al., 2015; Sim et al., 2014; Chauhan et al., 2012; Byrne et al., 2007). Their anti-oxidant properties make them even more valuable compounds. As part of our investigations on organotindithio complexes (Srivastava et al., 2007), we herein report the synthesis and structure of the title compound.The title compound with
[Na(µ3-C6H14ONCS2)(µ2-H2O)(H2O)], is a two-dimensional polymer. Within this polymer, each NaI ion exhibits a distorted octahedral geometry (Fig. 1) made up from coordination by the S atom of one N-butyl-N-(2-hydroxyethyl)dithiocarbamate (L) anion, two hydroxy O atoms from two L ligands and three aqua ligands, of which two aqua ligands form bridging units between two NaI cations. The dithiocarbamate anion acts as a triply bridging ligand, where one S atom coordinates one sodium atom and the Ohydroxy atom coordinates two sodium atoms (Fig. 2). The aforementioned feature of multiple coordination modes leads to the formation of polymeric layers parallel to the bc plane with the hydrophobic butyl arms protruding up and down. In the L ligand, while the two S atoms are not chemically equivalent as only one is involved in bonding to the Na cation, the C—S bond lengths are identical at 1.726 (1) Å.Intermolecular O—H···S hydrogen bonds (Table 1) are observed in the inner part of each polymeric layer (Fig. 3). The layers are further packed along the a axis and held together by weak van der Waals forces.
In a recent publication, Howie et al. (2008) reported a structurally similar compound where the butyl substituent was replaced by a propyl substituent. The crystal structures of other sodium salts of dithiocarbamates, Na[S2CN(C2H5)2]·3H2O (Colapietro et al., 1968), Na[S2CN(CH2)4]·2H2O (Albertsson et al., 1980; Ymén, 1982), Na[S2CN(C3H7)2]·5H2O (Ymén, 1983) and Na[S2CN(CH3)2]·2H2O (Oskarsson & Ymén, 1983), Na[S2CN(CH2)5]·2H2O (Mafud & Gambardella, 2011), Na[S2CN(C8H5NS)]·3H2O Téllez et al., 2004) have been reported. All these structures are polymeric in nature and contain the µ(H2O)2Na2 unit.
The title compound was prepared by the reaction of N-butyl N-hydroxyethyl amine (0.01 mol), carbon disulfide (0.01 mol) and sodium hydroxide (0.01 mol) in a dry diethyl ether and was stirred for 4 h at 253 K. The crude product was recrystallized from isopropyl alcohol. It was then dissolved in a hexane:diethyl ether (1:1) mixture and put in a deep freezer overnight. Square transparent crystals suitable for X ray analysis were obtained in 80% yield (m.p.: 430 K). Analysis calculated for C14H36N2O6S4 (%) S, 29.78; found: S, 29.84.
Crystal data, data collection and structure
details are summarized in Table 2. A l l C-bound H atoms were idealized with C—H distances of 0.99 Å for CH2 and 0.98 Å for CH3 groups with atomic displacement parameters of Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The water and hydroxyl H atoms were refined isotropically.Dithiocarbamates have recently drawn more attention due to their application in group-transfer radical
reactions (Grainger & Innocenti, 2007) and as ligands for chelating metals (Greenwood & Earnshaw, 1997). In recent years, their applications have not only become apparent as pesticides and fungicides, but they have also been widely used as vulcanization accelerators in the rubber industry (Svetlik et al., 1955). Dithiocarbamates are also of biological importance due to their anticancer, antibacterial, antituberculosis and antifungal properties (Li et al., 2015; Sim et al., 2014; Chauhan et al., 2012; Byrne et al., 2007). Their anti-oxidant properties make them even more valuable compounds. As part of our investigations on organotindithio complexes (Srivastava et al., 2007), we herein report the synthesis and structure of the title compound.The title compound with
[Na(µ3-C6H14ONCS2)(µ2-H2O)(H2O)], is a two-dimensional polymer. Within this polymer, each NaI ion exhibits a distorted octahedral geometry (Fig. 1) made up from coordination by the S atom of one N-butyl-N-(2-hydroxyethyl)dithiocarbamate (L) anion, two hydroxy O atoms from two L ligands and three aqua ligands, of which two aqua ligands form bridging units between two NaI cations. The dithiocarbamate anion acts as a triply bridging ligand, where one S atom coordinates one sodium atom and the Ohydroxy atom coordinates two sodium atoms (Fig. 2). The aforementioned feature of multiple coordination modes leads to the formation of polymeric layers parallel to the bc plane with the hydrophobic butyl arms protruding up and down. In the L ligand, while the two S atoms are not chemically equivalent as only one is involved in bonding to the Na cation, the C—S bond lengths are identical at 1.726 (1) Å.Intermolecular O—H···S hydrogen bonds (Table 1) are observed in the inner part of each polymeric layer (Fig. 3). The layers are further packed along the a axis and held together by weak van der Waals forces.
In a recent publication, Howie et al. (2008) reported a structurally similar compound where the butyl substituent was replaced by a propyl substituent. The crystal structures of other sodium salts of dithiocarbamates, Na[S2CN(C2H5)2]·3H2O (Colapietro et al., 1968), Na[S2CN(CH2)4]·2H2O (Albertsson et al., 1980; Ymén, 1982), Na[S2CN(C3H7)2]·5H2O (Ymén, 1983) and Na[S2CN(CH3)2]·2H2O (Oskarsson & Ymén, 1983), Na[S2CN(CH2)5]·2H2O (Mafud & Gambardella, 2011), Na[S2CN(C8H5NS)]·3H2O Téllez et al., 2004) have been reported. All these structures are polymeric in nature and contain the µ(H2O)2Na2 unit.
The title compound was prepared by the reaction of N-butyl N-hydroxyethyl amine (0.01 mol), carbon disulfide (0.01 mol) and sodium hydroxide (0.01 mol) in a dry diethyl ether and was stirred for 4 h at 253 K. The crude product was recrystallized from isopropyl alcohol. It was then dissolved in a hexane:diethyl ether (1:1) mixture and put in a deep freezer overnight. Square transparent crystals suitable for X ray analysis were obtained in 80% yield (m.p.: 430 K). Analysis calculated for C14H36N2O6S4 (%) S, 29.78; found: S, 29.84.
detailsCrystal data, data collection and structure
details are summarized in Table 2. A l l C-bound H atoms were idealized with C—H distances of 0.99 Å for CH2 and 0.98 Å for CH3 groups with atomic displacement parameters of Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The water and hydroxyl H atoms were refined isotropically.Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. A portion of the title crystal structure showing the coordination geometry for one Na cation and the atomic labels [symmetry codes: (A) 1 − x, y − 1/2, 1/2 − z; (B) 1 − x, −y, 1 − z]. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. Diagram showing the triply bridging nature of the dithiocarbamate anion [symmetry codes: (A) 1 − x, −y, 1 − z; (B) 1 − x, y + 1/2, 1/2 − z]. | |
Fig. 3. A portion of the crystal packing showing the O—H···S hydrogen bonds (dashed lines) in the inner part of the polymeric layer [symmetry codes: (A) 1 − x, 1 − y, 1 − z; (B) 1 − x, y − 1/2, 1/2 − z; (C) 1 − x, −y, 1 − z; (D) x, 3/2 − y, 1/2 + z; (E) x, 1 + y, z; (F) x, 1/2 − y, 1/2 + x]. |
[Na(C7H14NOS2)(H2O)2] | F(000) = 536 |
Mr = 251.33 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 15.6223 (3) Å | Cell parameters from 4003 reflections |
b = 5.8379 (1) Å | θ = 3.1–76.6° |
c = 14.7114 (3) Å | µ = 3.90 mm−1 |
β = 101.868 (2)° | T = 120 K |
V = 1313.02 (4) Å3 | Chunk, colorless |
Z = 4 | 0.39 × 0.31 × 0.24 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 2731 independent reflections |
Radiation source: sealed X-ray tube | 2617 reflections with I > 2σ(I) |
Detector resolution: 10.6501 pixels mm-1 | Rint = 0.019 |
ω scans | θmax = 76.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −19→17 |
Tmin = 0.660, Tmax = 1.000 | k = −7→4 |
5973 measured reflections | l = −18→17 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.3898P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.080 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.29 e Å−3 |
2731 reflections | Δρmin = −0.39 e Å−3 |
149 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0041 (4) |
[Na(C7H14NOS2)(H2O)2] | V = 1313.02 (4) Å3 |
Mr = 251.33 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 15.6223 (3) Å | µ = 3.90 mm−1 |
b = 5.8379 (1) Å | T = 120 K |
c = 14.7114 (3) Å | 0.39 × 0.31 × 0.24 mm |
β = 101.868 (2)° |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 2731 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 2617 reflections with I > 2σ(I) |
Tmin = 0.660, Tmax = 1.000 | Rint = 0.019 |
5973 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.29 e Å−3 |
2731 reflections | Δρmin = −0.39 e Å−3 |
149 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. |
x | y | z | Uiso*/Ueq | ||
Na1 | 0.44835 (3) | 0.26004 (8) | 0.45654 (3) | 0.01595 (14) | |
S1 | 0.76058 (2) | 0.34854 (5) | 0.14289 (2) | 0.01645 (11) | |
S2 | 0.60961 (2) | 0.50629 (5) | 0.22351 (2) | 0.01569 (11) | |
O1 | 0.59309 (6) | 0.09872 (16) | 0.47496 (6) | 0.0155 (2) | |
H1O | 0.6306 (14) | 0.125 (4) | 0.5218 (15) | 0.035 (5)* | |
O1W | 0.50061 (6) | 0.58495 (17) | 0.39025 (6) | 0.0172 (2) | |
H1W1 | 0.5325 (15) | 0.551 (4) | 0.3542 (15) | 0.039 (6)* | |
H1W2 | 0.4670 (16) | 0.686 (4) | 0.3609 (16) | 0.046 (6)* | |
O2W | 0.30199 (7) | 0.34773 (19) | 0.44462 (7) | 0.0220 (2) | |
H2W1 | 0.2792 (15) | 0.233 (4) | 0.4121 (16) | 0.041 (6)* | |
H2W2 | 0.2843 (15) | 0.462 (4) | 0.4197 (15) | 0.036 (6)* | |
N1 | 0.73937 (7) | 0.23989 (18) | 0.31192 (7) | 0.0149 (2) | |
C1 | 0.70580 (8) | 0.3542 (2) | 0.23350 (8) | 0.0138 (2) | |
C2 | 0.70139 (8) | 0.2560 (2) | 0.39489 (8) | 0.0154 (3) | |
H2A | 0.6735 | 0.4079 | 0.3964 | 0.019* | |
H2B | 0.7485 | 0.2424 | 0.4510 | 0.019* | |
C3 | 0.63355 (8) | 0.0692 (2) | 0.39629 (8) | 0.0167 (3) | |
H3A | 0.5884 | 0.0758 | 0.3383 | 0.020* | |
H3B | 0.6621 | −0.0828 | 0.3996 | 0.020* | |
C4 | 0.82101 (9) | 0.1072 (2) | 0.32374 (9) | 0.0197 (3) | |
H4A | 0.8270 | 0.0440 | 0.2629 | 0.024* | |
H4B | 0.8184 | −0.0229 | 0.3662 | 0.024* | |
C5 | 0.90068 (9) | 0.2546 (3) | 0.36299 (10) | 0.0269 (3) | |
H5A | 0.9006 | 0.3906 | 0.3228 | 0.032* | |
H5B | 0.8963 | 0.3091 | 0.4256 | 0.032* | |
C6 | 0.98645 (11) | 0.1266 (4) | 0.36977 (15) | 0.0465 (5) | |
H6A | 0.9929 | 0.0811 | 0.3067 | 0.056* | |
H6B | 0.9852 | −0.0147 | 0.4067 | 0.056* | |
C7 | 1.06488 (12) | 0.2721 (5) | 0.41491 (19) | 0.0658 (8) | |
H7A | 1.1185 | 0.1809 | 0.4213 | 0.099* | |
H7B | 1.0576 | 0.3224 | 0.4764 | 0.099* | |
H7C | 1.0689 | 0.4063 | 0.3760 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0155 (3) | 0.0175 (3) | 0.0152 (2) | −0.00088 (18) | 0.00403 (19) | 0.00032 (18) |
S1 | 0.01710 (17) | 0.02187 (18) | 0.01177 (17) | 0.00208 (11) | 0.00623 (12) | 0.00148 (10) |
S2 | 0.01414 (17) | 0.02106 (18) | 0.01238 (17) | 0.00310 (10) | 0.00394 (11) | 0.00173 (10) |
O1 | 0.0133 (4) | 0.0226 (5) | 0.0114 (4) | −0.0007 (3) | 0.0044 (3) | 0.0013 (3) |
O1W | 0.0175 (4) | 0.0200 (5) | 0.0152 (4) | 0.0025 (4) | 0.0061 (4) | 0.0011 (4) |
O2W | 0.0203 (5) | 0.0190 (5) | 0.0257 (5) | 0.0024 (4) | 0.0024 (4) | −0.0033 (4) |
N1 | 0.0121 (5) | 0.0214 (5) | 0.0118 (5) | 0.0007 (4) | 0.0040 (4) | 0.0013 (4) |
C1 | 0.0136 (6) | 0.0157 (6) | 0.0118 (5) | −0.0035 (4) | 0.0020 (4) | −0.0014 (4) |
C2 | 0.0141 (6) | 0.0226 (6) | 0.0100 (5) | −0.0014 (5) | 0.0036 (4) | 0.0014 (4) |
C3 | 0.0174 (6) | 0.0211 (6) | 0.0130 (6) | −0.0013 (5) | 0.0062 (4) | −0.0006 (5) |
C4 | 0.0166 (6) | 0.0260 (6) | 0.0167 (6) | 0.0060 (5) | 0.0038 (5) | 0.0034 (5) |
C5 | 0.0143 (7) | 0.0410 (9) | 0.0250 (7) | 0.0026 (6) | 0.0027 (5) | −0.0022 (6) |
C6 | 0.0172 (8) | 0.0670 (13) | 0.0528 (11) | 0.0100 (8) | 0.0015 (7) | −0.0184 (10) |
C7 | 0.0139 (8) | 0.0942 (19) | 0.0856 (18) | 0.0041 (10) | 0.0015 (9) | −0.0321 (15) |
Na1—O2W | 2.3142 (11) | N1—C1 | 1.3425 (16) |
Na1—O1W | 2.3544 (11) | N1—C2 | 1.4658 (15) |
Na1—O1Wi | 2.4074 (11) | N1—C4 | 1.4717 (16) |
Na1—O1 | 2.4128 (10) | C2—C3 | 1.5237 (17) |
Na1—O1ii | 2.4677 (10) | C2—H2A | 0.9900 |
Na1—S2iii | 3.0074 (6) | C2—H2B | 0.9900 |
Na1—Na1i | 3.3527 (10) | C3—H3A | 0.9900 |
Na1—Na1ii | 3.5509 (10) | C3—H3B | 0.9900 |
Na1—H2W1 | 2.59 (2) | C4—C5 | 1.525 (2) |
S1—C1 | 1.7261 (13) | C4—H4A | 0.9900 |
S2—C1 | 1.7256 (13) | C4—H4B | 0.9900 |
S2—Na1iv | 3.0073 (6) | C5—C6 | 1.519 (2) |
O1—C3 | 1.4386 (14) | C5—H5A | 0.9900 |
O1—Na1ii | 2.4677 (10) | C5—H5B | 0.9900 |
O1—H1O | 0.82 (2) | C6—C7 | 1.526 (3) |
O1W—Na1i | 2.4074 (10) | C6—H6A | 0.9900 |
O1W—H1W1 | 0.82 (2) | C6—H6B | 0.9900 |
O1W—H1W2 | 0.85 (3) | C7—H7A | 0.9800 |
O2W—H2W1 | 0.86 (2) | C7—H7B | 0.9800 |
O2W—H2W2 | 0.78 (2) | C7—H7C | 0.9800 |
O2W—Na1—O1W | 102.22 (4) | Na1i—O1W—H1W2 | 105.5 (16) |
O2W—Na1—O1Wi | 96.88 (4) | H1W1—O1W—H1W2 | 103 (2) |
O1W—Na1—O1Wi | 90.49 (4) | Na1—O2W—H2W1 | 99.2 (15) |
O2W—Na1—O1 | 169.54 (4) | Na1—O2W—H2W2 | 118.2 (16) |
O1W—Na1—O1 | 87.95 (4) | H2W1—O2W—H2W2 | 110 (2) |
O1Wi—Na1—O1 | 85.37 (4) | C1—N1—C2 | 122.02 (10) |
O2W—Na1—O1ii | 83.15 (4) | C1—N1—C4 | 122.61 (11) |
O1W—Na1—O1ii | 174.49 (4) | C2—N1—C4 | 115.15 (10) |
O1Wi—Na1—O1ii | 90.05 (4) | N1—C1—S2 | 120.56 (9) |
O1—Na1—O1ii | 86.64 (3) | N1—C1—S1 | 119.09 (9) |
O2W—Na1—S2iii | 85.90 (3) | S2—C1—S1 | 120.36 (7) |
O1W—Na1—S2iii | 95.69 (3) | N1—C2—C3 | 111.54 (10) |
O1Wi—Na1—S2iii | 172.54 (3) | N1—C2—H2A | 109.3 |
O1—Na1—S2iii | 90.69 (3) | C3—C2—H2A | 109.3 |
O1ii—Na1—S2iii | 83.39 (3) | N1—C2—H2B | 109.3 |
O2W—Na1—Na1i | 103.57 (4) | C3—C2—H2B | 109.3 |
O1W—Na1—Na1i | 45.89 (3) | H2A—C2—H2B | 108.0 |
O1Wi—Na1—Na1i | 44.60 (3) | O1—C3—C2 | 110.32 (10) |
O1—Na1—Na1i | 85.23 (3) | O1—C3—H3A | 109.6 |
O1ii—Na1—Na1i | 134.40 (3) | C2—C3—H3A | 109.6 |
S2iii—Na1—Na1i | 141.41 (3) | O1—C3—H3B | 109.6 |
O2W—Na1—Na1ii | 125.82 (4) | C2—C3—H3B | 109.6 |
O1W—Na1—Na1ii | 131.86 (3) | H3A—C3—H3B | 108.1 |
O1Wi—Na1—Na1ii | 86.89 (3) | N1—C4—C5 | 111.56 (12) |
O1—Na1—Na1ii | 43.93 (2) | N1—C4—H4A | 109.3 |
O1ii—Na1—Na1ii | 42.71 (2) | C5—C4—H4A | 109.3 |
S2iii—Na1—Na1ii | 85.882 (19) | N1—C4—H4B | 109.3 |
Na1i—Na1—Na1ii | 115.45 (3) | C5—C4—H4B | 109.3 |
O2W—Na1—H2W1 | 19.0 (5) | H4A—C4—H4B | 108.0 |
O1W—Na1—H2W1 | 111.5 (5) | C6—C5—C4 | 112.80 (14) |
O1Wi—Na1—H2W1 | 112.5 (5) | C6—C5—H5A | 109.0 |
O1—Na1—H2W1 | 152.6 (6) | C4—C5—H5A | 109.0 |
O1ii—Na1—H2W1 | 73.3 (5) | C6—C5—H5B | 109.0 |
S2iii—Na1—H2W1 | 69.0 (5) | C4—C5—H5B | 109.0 |
Na1i—Na1—H2W1 | 122.2 (5) | H5A—C5—H5B | 107.8 |
Na1ii—Na1—H2W1 | 113.8 (5) | C5—C6—C7 | 111.93 (18) |
C1—S2—Na1iv | 115.32 (4) | C5—C6—H6A | 109.2 |
C3—O1—Na1 | 120.87 (7) | C7—C6—H6A | 109.2 |
C3—O1—Na1ii | 115.00 (8) | C5—C6—H6B | 109.2 |
Na1—O1—Na1ii | 93.36 (3) | C7—C6—H6B | 109.2 |
C3—O1—H1O | 109.9 (14) | H6A—C6—H6B | 107.9 |
Na1—O1—H1O | 120.7 (14) | C6—C7—H7A | 109.5 |
Na1ii—O1—H1O | 91.1 (15) | C6—C7—H7B | 109.5 |
Na1—O1W—Na1i | 89.50 (4) | H7A—C7—H7B | 109.5 |
Na1—O1W—H1W1 | 112.5 (16) | C6—C7—H7C | 109.5 |
Na1i—O1W—H1W1 | 124.5 (15) | H7A—C7—H7C | 109.5 |
Na1—O1W—H1W2 | 122.7 (16) | H7B—C7—H7C | 109.5 |
C2—N1—C1—S2 | −5.92 (16) | Na1—O1—C3—C2 | 102.88 (10) |
C4—N1—C1—S2 | 179.80 (9) | Na1ii—O1—C3—C2 | −146.38 (8) |
C2—N1—C1—S1 | 173.66 (9) | N1—C2—C3—O1 | −176.02 (9) |
C4—N1—C1—S1 | −0.62 (16) | C1—N1—C4—C5 | 89.35 (15) |
Na1iv—S2—C1—N1 | 178.00 (8) | C2—N1—C4—C5 | −85.29 (13) |
Na1iv—S2—C1—S1 | −1.57 (9) | N1—C4—C5—C6 | −176.06 (13) |
C1—N1—C2—C3 | 91.65 (14) | C4—C5—C6—C7 | −176.34 (18) |
C4—N1—C2—C3 | −93.68 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···S1v | 0.82 (2) | 2.41 (2) | 3.2227 (10) | 167.6 (19) |
O1W—H1W1···S2 | 0.82 (2) | 2.48 (2) | 3.2933 (10) | 168 (2) |
O1W—H1W2···S2iv | 0.85 (3) | 2.42 (3) | 3.2605 (10) | 171 (2) |
O2W—H2W2···S1iv | 0.78 (2) | 2.48 (2) | 3.2624 (11) | 173 (2) |
Symmetry codes: (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···S1i | 0.82 (2) | 2.41 (2) | 3.2227 (10) | 167.6 (19) |
O1W—H1W1···S2 | 0.82 (2) | 2.48 (2) | 3.2933 (10) | 168 (2) |
O1W—H1W2···S2ii | 0.85 (3) | 2.42 (3) | 3.2605 (10) | 171 (2) |
O2W—H2W2···S1ii | 0.78 (2) | 2.48 (2) | 3.2624 (11) | 173 (2) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Na(C7H14NOS2)(H2O)2] |
Mr | 251.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 15.6223 (3), 5.8379 (1), 14.7114 (3) |
β (°) | 101.868 (2) |
V (Å3) | 1313.02 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.90 |
Crystal size (mm) | 0.39 × 0.31 × 0.24 |
Data collection | |
Diffractometer | Agilent SuperNova Dual Source diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.660, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5973, 2731, 2617 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.631 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.080, 1.05 |
No. of reflections | 2731 |
No. of parameters | 149 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.39 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015).
Acknowledgements
RJB acknowledges NSF award 1205608, Partnership for Reduced Dimensional Materials, for partial funding of this research and the Department of Chemistry, University of Canterbury, New Zealand, for access to their diffractometer during the visit in 2014.
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