organic compounds
2-Chloro-N-(4-methoxybenzoyl)benzenesulfonamide
aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, cDepartment of Studies in Microbiology, University of Mysore, Manasagangotri, Mysore, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in
In the title compound, C14H12ClNO4S, the dihedral angle between the aromatic rings is 82.07 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 82.46 (3)°. In the crystal, the molecules are linked into C(4) chains running along [001] by strong N—H⋯O hydrogen bonds. A C—H⋯O interaction reinforces the [001] chains: its graph-set symbol is C(7). The chains are cross-linked into (100) sheets by further C—H⋯O interactions as C(6) chains along [001]. The structure also features weak π–π stacking interactions [centroid–centroid distances = 3.577 (1) and 3.8016 (1) Å].
CCDC reference: 978144
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 978144
10.1107/S1600536814001482/hb7189sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001482/hb7189Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001482/hb7189Isup3.cml
As a part of our continued structural studies of N-(aroyl)-arylsulfonamides (Suchetan et al., 2011a, 2011b; Gowda et al., 2010a, 2010b), we report here the
of the title compound (I) (Fig 1).The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 445 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.
The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).
In I, the dihedral angle between the two aromatic rings is 82.07 (1)°. Compared to this, the dihedral angle is 73.3 (1)° in N-(benzoyl)-2-chlorobenzenesulfonamide (II, Gowda et al., 2010a), 85.7 (1)° in N-(4-chlorobenzoyl)-2-chlorobenzenesulfonamide (III, Suchetan et al., 2011a), 89.1 (2)° in N-(4-methylbenzoyl)-2-chlorobenzenesulfonamide (IV, Gowda et al., 2010b) and 85.4 (1)° in N-(4-nitrobenzoyl)-2-chlorobenzenesulfonamide (V, Suchetan et al., 2011b). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 82.46 (3)°.
In the π-π interactions, Cg(methoxyphenyl)-Cg(methoxyphenyl) and Cg(chlorophenyl)-Cg(chlorophenyl) distances being respectively 3.577 (1)Å and 3.8016 (1)Å.
the molecules are linked into C(4) chains running along [001] through strong N1—H1···O2 hydrogen bonds (Figure 2). The molecules are further linked into one another through C3—H3···O1 (Figure 3) and C9—H9···O2 (Figure 4) interactions into C(6) and C(7) chains running along [001]. The structure is further stabilized by two alternateAs a part of our continued structural studies of N-(aroyl)-arylsulfonamides (Suchetan et al., 2011a, 2011b; Gowda et al., 2010a, 2010b), we report here the
of the title compound (I) (Fig 1).In I, the dihedral angle between the two aromatic rings is 82.07 (1)°. Compared to this, the dihedral angle is 73.3 (1)° in N-(benzoyl)-2-chlorobenzenesulfonamide (II, Gowda et al., 2010a), 85.7 (1)° in N-(4-chlorobenzoyl)-2-chlorobenzenesulfonamide (III, Suchetan et al., 2011a), 89.1 (2)° in N-(4-methylbenzoyl)-2-chlorobenzenesulfonamide (IV, Gowda et al., 2010b) and 85.4 (1)° in N-(4-nitrobenzoyl)-2-chlorobenzenesulfonamide (V, Suchetan et al., 2011b). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 82.46 (3)°.
In the π-π interactions, Cg(methoxyphenyl)-Cg(methoxyphenyl) and Cg(chlorophenyl)-Cg(chlorophenyl) distances being respectively 3.577 (1)Å and 3.8016 (1)Å.
the molecules are linked into C(4) chains running along [001] through strong N1—H1···O2 hydrogen bonds (Figure 2). The molecules are further linked into one another through C3—H3···O1 (Figure 3) and C9—H9···O2 (Figure 4) interactions into C(6) and C(7) chains running along [001]. The structure is further stabilized by two alternateFor related structures see: Gowda et al. (2010a,b); Suchetan et al. (2011a,b).
The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 445 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.
detailsThe H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H12ClNO4S | Prism |
Mr = 325.76 | Dx = 1.448 Mg m−3 |
Monoclinic, P21/c | Melting point: 445 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54178 Å |
a = 14.5293 (19) Å | Cell parameters from 25 reflections |
b = 10.6225 (14) Å | θ = 3.0–64.6° |
c = 9.6918 (14) Å | µ = 3.71 mm−1 |
β = 92.695 (5)° | T = 293 K |
V = 1494.2 (4) Å3 | Prism, colourless |
Z = 4 | 0.44 × 0.35 × 0.26 mm |
F(000) = 672 |
Bruker APEXII CCD diffractometer | 2449 independent reflections |
Radiation source: fine-focus sealed tube | 2295 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
phi and φ scans | θmax = 64.6°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −16→16 |
Tmin = 0.263, Tmax = 0.381 | k = −12→12 |
17846 measured reflections | l = −11→9 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.109P)2 + 0.3886P] where P = (Fo2 + 2Fc2)/3 |
2449 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C14H12ClNO4S | V = 1494.2 (4) Å3 |
Mr = 325.76 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 14.5293 (19) Å | µ = 3.71 mm−1 |
b = 10.6225 (14) Å | T = 293 K |
c = 9.6918 (14) Å | 0.44 × 0.35 × 0.26 mm |
β = 92.695 (5)° |
Bruker APEXII CCD diffractometer | 2449 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2295 reflections with I > 2σ(I) |
Tmin = 0.263, Tmax = 0.381 | Rint = 0.058 |
17846 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.52 e Å−3 |
2449 reflections | Δρmin = −0.37 e Å−3 |
195 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
H1 | 0.718 (2) | 0.192 (3) | 0.295 (4) | 0.066 (10)* | |
S1 | 0.79503 (4) | 0.19067 (5) | 0.11546 (6) | 0.0448 (3) | |
Cl1 | 0.90252 (7) | 0.02535 (9) | 0.35628 (9) | 0.0882 (4) | |
O1 | 0.85786 (12) | 0.27002 (19) | 0.1915 (2) | 0.0592 (5) | |
O2 | 0.75657 (13) | 0.2343 (2) | −0.01265 (19) | 0.0645 (5) | |
O4 | 0.32115 (14) | 0.1078 (2) | 0.5017 (3) | 0.0826 (7) | |
C9 | 0.54708 (16) | 0.1902 (2) | 0.3736 (3) | 0.0497 (6) | |
H9 | 0.5956 | 0.2456 | 0.3921 | 0.060* | |
C8 | 0.55277 (15) | 0.1039 (2) | 0.2671 (2) | 0.0439 (5) | |
C7 | 0.63122 (16) | 0.0964 (2) | 0.1759 (2) | 0.0467 (6) | |
N1 | 0.71064 (13) | 0.1640 (2) | 0.2183 (2) | 0.0482 (5) | |
O3 | 0.62999 (14) | 0.0385 (2) | 0.0682 (2) | 0.0705 (6) | |
C10 | 0.47035 (18) | 0.1952 (3) | 0.4531 (3) | 0.0562 (7) | |
H10 | 0.4673 | 0.2543 | 0.5235 | 0.067* | |
C13 | 0.47841 (19) | 0.0229 (3) | 0.2399 (3) | 0.0603 (7) | |
H13 | 0.4801 | −0.0340 | 0.1671 | 0.072* | |
C1 | 0.84769 (15) | 0.0440 (2) | 0.0838 (3) | 0.0485 (6) | |
C11 | 0.39843 (17) | 0.1122 (3) | 0.4276 (3) | 0.0565 (6) | |
C2 | 0.89668 (17) | −0.0230 (3) | 0.1868 (3) | 0.0604 (7) | |
C12 | 0.4026 (2) | 0.0265 (3) | 0.3197 (4) | 0.0679 (8) | |
H12 | 0.3539 | −0.0287 | 0.3013 | 0.081* | |
C3 | 0.9432 (2) | −0.1334 (3) | 0.1497 (5) | 0.0842 (12) | |
H3 | 0.9776 | −0.1787 | 0.2160 | 0.101* | |
C6 | 0.8439 (2) | 0.0008 (3) | −0.0515 (3) | 0.0638 (7) | |
H6 | 0.8105 | 0.0453 | −0.1195 | 0.077* | |
C4 | 0.9373 (3) | −0.1740 (3) | 0.0131 (5) | 0.0893 (12) | |
H4 | 0.9668 | −0.2481 | −0.0107 | 0.107* | |
C5 | 0.8897 (3) | −0.1082 (4) | −0.0854 (5) | 0.0851 (11) | |
H5 | 0.8877 | −0.1362 | −0.1765 | 0.102* | |
C14 | 0.3152 (3) | 0.1932 (4) | 0.6139 (5) | 0.0940 (13) | |
H14A | 0.3676 | 0.1823 | 0.6768 | 0.141* | |
H14B | 0.2598 | 0.1771 | 0.6612 | 0.141* | |
H14C | 0.3141 | 0.2780 | 0.5795 | 0.141* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0411 (4) | 0.0523 (4) | 0.0410 (4) | 0.0020 (2) | 0.0010 (3) | 0.0046 (2) |
Cl1 | 0.0929 (6) | 0.0998 (7) | 0.0690 (6) | −0.0016 (5) | −0.0274 (4) | 0.0253 (4) |
O1 | 0.0552 (10) | 0.0589 (10) | 0.0636 (12) | −0.0150 (8) | 0.0034 (8) | −0.0062 (8) |
O2 | 0.0623 (11) | 0.0852 (13) | 0.0459 (10) | 0.0168 (10) | 0.0013 (8) | 0.0179 (9) |
O4 | 0.0488 (11) | 0.0906 (16) | 0.1105 (19) | −0.0120 (10) | 0.0257 (11) | −0.0087 (13) |
C9 | 0.0382 (12) | 0.0555 (14) | 0.0552 (15) | −0.0069 (9) | −0.0011 (10) | −0.0066 (10) |
C8 | 0.0404 (11) | 0.0450 (12) | 0.0459 (12) | −0.0027 (9) | −0.0037 (9) | 0.0013 (10) |
C7 | 0.0436 (12) | 0.0541 (13) | 0.0418 (13) | 0.0007 (10) | −0.0048 (9) | −0.0023 (10) |
N1 | 0.0421 (10) | 0.0628 (12) | 0.0394 (12) | −0.0026 (9) | −0.0010 (8) | −0.0064 (10) |
O3 | 0.0594 (11) | 0.0961 (15) | 0.0557 (12) | −0.0101 (10) | 0.0010 (9) | −0.0290 (11) |
C10 | 0.0429 (13) | 0.0642 (16) | 0.0616 (16) | −0.0030 (10) | 0.0047 (11) | −0.0110 (12) |
C13 | 0.0529 (14) | 0.0595 (15) | 0.0681 (17) | −0.0110 (12) | −0.0015 (12) | −0.0141 (13) |
C1 | 0.0368 (11) | 0.0534 (13) | 0.0555 (14) | −0.0019 (9) | 0.0043 (10) | 0.0023 (11) |
C11 | 0.0406 (12) | 0.0594 (15) | 0.0697 (17) | −0.0029 (11) | 0.0055 (11) | 0.0053 (13) |
C2 | 0.0396 (12) | 0.0604 (16) | 0.0806 (19) | −0.0003 (11) | −0.0018 (12) | 0.0167 (13) |
C12 | 0.0467 (14) | 0.0664 (17) | 0.091 (2) | −0.0180 (12) | 0.0039 (13) | −0.0085 (15) |
C3 | 0.0488 (15) | 0.0647 (19) | 0.139 (4) | 0.0075 (13) | 0.0061 (18) | 0.030 (2) |
C6 | 0.0598 (15) | 0.0699 (17) | 0.0627 (17) | −0.0006 (13) | 0.0115 (13) | −0.0087 (14) |
C4 | 0.072 (2) | 0.066 (2) | 0.133 (4) | 0.0070 (16) | 0.032 (2) | −0.012 (2) |
C5 | 0.081 (2) | 0.077 (2) | 0.100 (3) | −0.0035 (18) | 0.030 (2) | −0.025 (2) |
C14 | 0.0640 (19) | 0.103 (3) | 0.119 (3) | 0.0030 (18) | 0.041 (2) | −0.016 (2) |
S1—O2 | 1.4154 (19) | C13—C12 | 1.375 (4) |
S1—O1 | 1.4227 (19) | C13—H13 | 0.9300 |
S1—N1 | 1.641 (2) | C1—C6 | 1.387 (4) |
S1—C1 | 1.769 (3) | C1—C2 | 1.394 (4) |
Cl1—C2 | 1.720 (3) | C11—C12 | 1.390 (5) |
O4—C11 | 1.362 (3) | C2—C3 | 1.408 (5) |
O4—C14 | 1.422 (5) | C12—H12 | 0.9300 |
C9—C10 | 1.385 (4) | C3—C4 | 1.391 (6) |
C9—C8 | 1.386 (4) | C3—H3 | 0.9300 |
C9—H9 | 0.9300 | C6—C5 | 1.383 (5) |
C8—C13 | 1.396 (3) | C6—H6 | 0.9300 |
C8—C7 | 1.477 (3) | C4—C5 | 1.348 (6) |
C7—O3 | 1.211 (3) | C4—H4 | 0.9300 |
C7—N1 | 1.404 (3) | C5—H5 | 0.9300 |
N1—H1 | 0.80 (4) | C14—H14A | 0.9600 |
C10—C11 | 1.381 (4) | C14—H14B | 0.9600 |
C10—H10 | 0.9300 | C14—H14C | 0.9600 |
O2—S1—O1 | 118.55 (13) | O4—C11—C10 | 124.3 (3) |
O2—S1—N1 | 108.28 (11) | O4—C11—C12 | 116.2 (2) |
O1—S1—N1 | 105.51 (11) | C10—C11—C12 | 119.6 (2) |
O2—S1—C1 | 106.98 (13) | C1—C2—C3 | 118.5 (3) |
O1—S1—C1 | 109.85 (12) | C1—C2—Cl1 | 122.2 (2) |
N1—S1—C1 | 107.16 (11) | C3—C2—Cl1 | 119.3 (3) |
C11—O4—C14 | 117.6 (2) | C13—C12—C11 | 120.4 (2) |
C10—C9—C8 | 121.2 (2) | C13—C12—H12 | 119.8 |
C10—C9—H9 | 119.4 | C11—C12—H12 | 119.8 |
C8—C9—H9 | 119.4 | C4—C3—C2 | 119.5 (3) |
C9—C8—C13 | 118.4 (2) | C4—C3—H3 | 120.2 |
C9—C8—C7 | 123.8 (2) | C2—C3—H3 | 120.2 |
C13—C8—C7 | 117.8 (2) | C5—C6—C1 | 120.3 (3) |
O3—C7—N1 | 119.4 (2) | C5—C6—H6 | 119.9 |
O3—C7—C8 | 124.2 (2) | C1—C6—H6 | 119.9 |
N1—C7—C8 | 116.4 (2) | C5—C4—C3 | 121.3 (3) |
C7—N1—S1 | 122.55 (18) | C5—C4—H4 | 119.4 |
C7—N1—H1 | 122 (2) | C3—C4—H4 | 119.4 |
S1—N1—H1 | 115 (2) | C4—C5—C6 | 120.1 (4) |
C11—C10—C9 | 119.9 (2) | C4—C5—H5 | 119.9 |
C11—C10—H10 | 120.1 | C6—C5—H5 | 119.9 |
C9—C10—H10 | 120.1 | O4—C14—H14A | 109.5 |
C12—C13—C8 | 120.6 (3) | O4—C14—H14B | 109.5 |
C12—C13—H13 | 119.7 | H14A—C14—H14B | 109.5 |
C8—C13—H13 | 119.7 | O4—C14—H14C | 109.5 |
C6—C1—C2 | 120.3 (3) | H14A—C14—H14C | 109.5 |
C6—C1—S1 | 117.2 (2) | H14B—C14—H14C | 109.5 |
C2—C1—S1 | 122.4 (2) | ||
C10—C9—C8—C13 | 1.0 (4) | N1—S1—C1—C2 | −67.4 (2) |
C10—C9—C8—C7 | 178.0 (2) | C14—O4—C11—C10 | −1.0 (5) |
C9—C8—C7—O3 | −165.9 (3) | C14—O4—C11—C12 | 179.3 (3) |
C13—C8—C7—O3 | 11.1 (4) | C9—C10—C11—O4 | 178.5 (3) |
C9—C8—C7—N1 | 12.8 (3) | C9—C10—C11—C12 | −1.8 (4) |
C13—C8—C7—N1 | −170.2 (2) | C6—C1—C2—C3 | 1.1 (4) |
O3—C7—N1—S1 | 12.0 (3) | S1—C1—C2—C3 | −174.5 (2) |
C8—C7—N1—S1 | −166.74 (17) | C6—C1—C2—Cl1 | −179.3 (2) |
O2—S1—N1—C7 | 47.2 (2) | S1—C1—C2—Cl1 | 5.1 (3) |
O1—S1—N1—C7 | 175.11 (19) | C8—C13—C12—C11 | 0.9 (5) |
C1—S1—N1—C7 | −67.9 (2) | O4—C11—C12—C13 | −179.3 (3) |
C8—C9—C10—C11 | 0.8 (4) | C10—C11—C12—C13 | 0.9 (5) |
C9—C8—C13—C12 | −1.9 (4) | C1—C2—C3—C4 | −1.5 (4) |
C7—C8—C13—C12 | −179.0 (3) | Cl1—C2—C3—C4 | 178.9 (3) |
O2—S1—C1—C6 | 0.9 (2) | C2—C1—C6—C5 | −0.8 (4) |
O1—S1—C1—C6 | −129.0 (2) | S1—C1—C6—C5 | 175.0 (2) |
N1—S1—C1—C6 | 116.9 (2) | C2—C3—C4—C5 | 1.6 (5) |
O2—S1—C1—C2 | 176.7 (2) | C3—C4—C5—C6 | −1.3 (6) |
O1—S1—C1—C2 | 46.8 (2) | C1—C6—C5—C4 | 0.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (3) | 2.09 (3) | 2.872 (3) | 172 (3) |
C3—H3···O1ii | 0.93 | 2.57 | 3.370 (4) | 144 |
C9—H9···O2i | 0.93 | 2.48 | 3.288 (3) | 145 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (3) | 2.09 (3) | 2.872 (3) | 172 (3) |
C3—H3···O1ii | 0.93 | 2.57 | 3.370 (4) | 144 |
C9—H9···O2i | 0.93 | 2.48 | 3.288 (3) | 145 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.
References
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