organic compounds
N-(4-Methylphenylsulfonyl)-3-nitrobenzamide
aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Chemistry, AVK College for Women, Davangere-2, India, cUniversity College of Science, Tumkur University, Tumkur, India, dDepartment of Studies in Microbiology, University of Mysore, Manasagangotri, Mysore, India, eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and fDepartment 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, C14H12N2O5S, the dihedral angle between the aromatic rings is 86.29 (1)° and the conformation between the C=O bond of the amide group and the meta-NO2 group is syn. The C—S—N—C torsion angle is −65.87 (19)° and the molecule has an L-shaped conformation. In the crystal, the molecules are connected into inversion dimers through pairs of N—H⋯O hydrogen bonds and C—H⋯O interactions forming R22(8) and R22(14) loops, respectively. The dimers are connected by further C—H⋯O interactions, thereby forming (100) sheets.
CCDC reference: 978140
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (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.
Supporting information
CCDC reference: 978140
10.1107/S1600536814001317/hb7184sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001317/hb7184Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001317/hb7184Isup3.cml
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2010, 2011, 2012), we report here the
of the title compound (I) (Fig 1).The title compound (I) was prepared by refluxing a mixture of 3-nitrobenzoic acid, 4-methylbenzenesulfonamide 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: 459 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 Ueq of the parent atom).
In I, the dihedral angle between the two aromatic rings is 86.29 (1)°. Compared to this, the dihedral angle is 79.4 (1)° in N-(4-methylphenylsulfonyl)-benzamide (II) (Suchetan et al., 2010), 89.8 (1)° in N-(4-methylphenylsulfonyl)-4-nitrobenzamide (III) (Suchetan et al., 2011) and 86.9 (2)° in N-(phenylsulfonyl)-3-nitrobenzamide (IV) (Suchetan et al., 2012). Thus, introducing a nitro group into the benzoyl ring results in an increase of the dihedral angle between the aromatic rings. The conformation between the N—H bond and the meta-NO2 group is anti in contrast to the syn conformation observed in IV (Suchetan et al., 2012). 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 rings being 79.16 (1)°.
In the
the molecules are connected into inversion dimers through N1—HN1···O2 hydrogen bonds (Table 1, Figure 2) and C13—H13···O2 interactions forming R22(8) and R22(14) ring motifs respectively. These dimers are further connected into C(12) chains through C3—H3···O4 interactions forming sheets (Figure 2).As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2010, 2011, 2012), we report here the
of the title compound (I) (Fig 1).In I, the dihedral angle between the two aromatic rings is 86.29 (1)°. Compared to this, the dihedral angle is 79.4 (1)° in N-(4-methylphenylsulfonyl)-benzamide (II) (Suchetan et al., 2010), 89.8 (1)° in N-(4-methylphenylsulfonyl)-4-nitrobenzamide (III) (Suchetan et al., 2011) and 86.9 (2)° in N-(phenylsulfonyl)-3-nitrobenzamide (IV) (Suchetan et al., 2012). Thus, introducing a nitro group into the benzoyl ring results in an increase of the dihedral angle between the aromatic rings. The conformation between the N—H bond and the meta-NO2 group is anti in contrast to the syn conformation observed in IV (Suchetan et al., 2012). 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 rings being 79.16 (1)°.
In the
the molecules are connected into inversion dimers through N1—HN1···O2 hydrogen bonds (Table 1, Figure 2) and C13—H13···O2 interactions forming R22(8) and R22(14) ring motifs respectively. These dimers are further connected into C(12) chains through C3—H3···O4 interactions forming sheets (Figure 2).For related structures see: Suchetan et al. (2010, 2011, 2012).
The title compound (I) was prepared by refluxing a mixture of 3-nitrobenzoic acid, 4-methylbenzenesulfonamide 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: 459 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 Ueq of the parent atom).
Data collection: APEX2 (Bruker, 2009); cell
APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (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).Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level. | |
Fig. 2. Formation of sheets in the crystal structure. |
C14H12N2O5S | Prism |
Mr = 320.32 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Melting point: 459 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54178 Å |
a = 4.9736 (5) Å | Cell parameters from 1127 reflections |
b = 23.245 (2) Å | θ = 3.8–64.5° |
c = 12.7197 (11) Å | µ = 2.24 mm−1 |
β = 100.820 (4)° | T = 293 K |
V = 1444.4 (2) Å3 | Prism, colourless |
Z = 4 | 0.39 × 0.29 × 0.20 mm |
F(000) = 664 |
Bruker APEXII diffractometer | 2053 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 64.5°, θmin = 3.8° |
phi and φ scans | h = −5→4 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −26→26 |
Tmin = 0.481, Tmax = 0.638 | l = −14→14 |
12115 measured reflections | 2 standard reflections every 1 reflections |
2378 independent reflections | intensity decay: 1% |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3691P] where P = (Fo2 + 2Fc2)/3 |
2378 reflections | (Δ/σ)max < 0.001 |
204 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C14H12N2O5S | V = 1444.4 (2) Å3 |
Mr = 320.32 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 4.9736 (5) Å | µ = 2.24 mm−1 |
b = 23.245 (2) Å | T = 293 K |
c = 12.7197 (11) Å | 0.39 × 0.29 × 0.20 mm |
β = 100.820 (4)° |
Bruker APEXII diffractometer | 2053 reflections with I > 2σ(I) |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | Rint = 0.035 |
Tmin = 0.481, Tmax = 0.638 | 2 standard reflections every 1 reflections |
12115 measured reflections | intensity decay: 1% |
2378 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.20 e Å−3 |
2378 reflections | Δρmin = −0.23 e Å−3 |
204 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 | ||
S1 | 1.10155 (10) | 0.50190 (2) | 0.32699 (4) | 0.0546 (2) | |
C8 | 0.6073 (4) | 0.63811 (8) | 0.33442 (15) | 0.0481 (5) | |
C9 | 0.4226 (4) | 0.66836 (8) | 0.25927 (16) | 0.0481 (5) | |
H9 | 0.4108 | 0.6615 | 0.1865 | 0.058* | |
O2 | 1.1994 (3) | 0.47252 (7) | 0.42557 (13) | 0.0667 (4) | |
N2 | 0.0629 (4) | 0.74082 (8) | 0.21424 (15) | 0.0570 (4) | |
O1 | 1.2908 (3) | 0.52526 (7) | 0.26821 (15) | 0.0720 (5) | |
N1 | 0.9164 (4) | 0.55519 (7) | 0.36288 (16) | 0.0534 (4) | |
C10 | 0.2572 (4) | 0.70859 (8) | 0.29425 (15) | 0.0471 (5) | |
O3 | 0.8066 (3) | 0.59550 (7) | 0.19878 (13) | 0.0695 (5) | |
O4 | −0.1159 (4) | 0.76822 (9) | 0.24399 (15) | 0.0891 (6) | |
O5 | 0.0900 (4) | 0.73809 (9) | 0.12131 (13) | 0.0853 (6) | |
C4 | 0.4935 (5) | 0.38740 (9) | 0.11605 (18) | 0.0593 (5) | |
C3 | 0.5450 (5) | 0.38158 (10) | 0.22531 (18) | 0.0646 (6) | |
H3 | 0.4508 | 0.3537 | 0.2563 | 0.077* | |
C7 | 0.7819 (4) | 0.59512 (9) | 0.29113 (17) | 0.0518 (5) | |
C5 | 0.6344 (5) | 0.42936 (10) | 0.07092 (18) | 0.0680 (6) | |
H5 | 0.6014 | 0.4341 | −0.0030 | 0.082* | |
C11 | 0.2669 (5) | 0.71991 (9) | 0.40117 (17) | 0.0583 (5) | |
H11 | 0.1494 | 0.7467 | 0.4229 | 0.070* | |
C1 | 0.8710 (4) | 0.45716 (8) | 0.24416 (16) | 0.0490 (5) | |
C6 | 0.8239 (5) | 0.46431 (10) | 0.13467 (19) | 0.0630 (6) | |
H6 | 0.9182 | 0.4923 | 0.1039 | 0.076* | |
C13 | 0.6243 (5) | 0.64965 (9) | 0.44227 (17) | 0.0602 (6) | |
H13 | 0.7500 | 0.6298 | 0.4928 | 0.072* | |
C2 | 0.7316 (5) | 0.41580 (10) | 0.29029 (17) | 0.0588 (5) | |
H2 | 0.7635 | 0.4111 | 0.3642 | 0.071* | |
C12 | 0.4558 (5) | 0.69042 (10) | 0.47530 (18) | 0.0669 (6) | |
H12 | 0.4696 | 0.6981 | 0.5479 | 0.080* | |
C14 | 0.2854 (6) | 0.34997 (12) | 0.0463 (2) | 0.0845 (8) | |
H14A | 0.1814 | 0.3292 | 0.0903 | 0.127* | |
H14B | 0.3776 | 0.3232 | 0.0078 | 0.127* | |
H14C | 0.1647 | 0.3736 | −0.0035 | 0.127* | |
HN1 | 0.860 (5) | 0.5495 (10) | 0.417 (2) | 0.062 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0368 (3) | 0.0518 (3) | 0.0732 (4) | 0.0021 (2) | 0.0053 (2) | −0.0047 (2) |
C8 | 0.0445 (11) | 0.0416 (10) | 0.0566 (11) | −0.0023 (8) | 0.0052 (9) | −0.0015 (8) |
C9 | 0.0469 (11) | 0.0478 (11) | 0.0488 (10) | −0.0051 (9) | 0.0071 (8) | −0.0001 (8) |
O2 | 0.0538 (9) | 0.0660 (10) | 0.0726 (10) | 0.0159 (7) | −0.0079 (7) | −0.0034 (8) |
N2 | 0.0582 (11) | 0.0534 (10) | 0.0563 (11) | 0.0032 (9) | 0.0024 (8) | 0.0041 (8) |
O1 | 0.0428 (8) | 0.0662 (10) | 0.1106 (13) | −0.0065 (7) | 0.0238 (8) | −0.0066 (9) |
N1 | 0.0444 (10) | 0.0513 (10) | 0.0627 (11) | 0.0046 (8) | 0.0053 (8) | −0.0017 (8) |
C10 | 0.0458 (11) | 0.0423 (10) | 0.0508 (11) | −0.0017 (8) | 0.0027 (8) | 0.0028 (8) |
O3 | 0.0759 (11) | 0.0679 (10) | 0.0705 (11) | 0.0121 (8) | 0.0292 (8) | 0.0079 (8) |
O4 | 0.0871 (13) | 0.0949 (14) | 0.0821 (12) | 0.0449 (11) | 0.0077 (10) | 0.0063 (10) |
O5 | 0.0957 (14) | 0.1043 (14) | 0.0529 (10) | 0.0235 (11) | 0.0063 (9) | 0.0148 (9) |
C4 | 0.0611 (13) | 0.0514 (12) | 0.0619 (13) | 0.0011 (10) | 0.0025 (10) | −0.0020 (10) |
C3 | 0.0647 (14) | 0.0599 (13) | 0.0669 (14) | −0.0144 (11) | 0.0066 (11) | 0.0075 (11) |
C7 | 0.0448 (11) | 0.0488 (11) | 0.0612 (13) | −0.0026 (9) | 0.0084 (9) | −0.0004 (9) |
C5 | 0.0866 (17) | 0.0651 (14) | 0.0516 (12) | −0.0038 (12) | 0.0111 (11) | −0.0008 (10) |
C11 | 0.0665 (14) | 0.0519 (11) | 0.0551 (12) | 0.0116 (10) | 0.0082 (10) | −0.0036 (9) |
C1 | 0.0414 (11) | 0.0471 (10) | 0.0587 (12) | 0.0034 (8) | 0.0100 (8) | −0.0014 (9) |
C6 | 0.0686 (15) | 0.0589 (13) | 0.0647 (13) | −0.0080 (11) | 0.0207 (11) | 0.0028 (10) |
C13 | 0.0670 (14) | 0.0536 (12) | 0.0540 (12) | 0.0093 (10) | −0.0041 (10) | 0.0001 (9) |
C2 | 0.0591 (13) | 0.0605 (13) | 0.0546 (12) | −0.0081 (10) | 0.0054 (10) | 0.0051 (10) |
C12 | 0.0871 (17) | 0.0623 (14) | 0.0471 (11) | 0.0166 (12) | 0.0017 (11) | −0.0057 (10) |
C14 | 0.096 (2) | 0.0701 (16) | 0.0780 (17) | −0.0173 (14) | −0.0082 (14) | −0.0066 (13) |
S1—O1 | 1.4156 (17) | C4—C14 | 1.507 (3) |
S1—O2 | 1.4305 (16) | C3—C2 | 1.375 (3) |
S1—N1 | 1.6580 (18) | C3—H3 | 0.9300 |
S1—C1 | 1.747 (2) | C5—C6 | 1.385 (3) |
C8—C13 | 1.385 (3) | C5—H5 | 0.9300 |
C8—C9 | 1.386 (3) | C11—C12 | 1.382 (3) |
C8—C7 | 1.495 (3) | C11—H11 | 0.9300 |
C9—C10 | 1.373 (3) | C1—C6 | 1.378 (3) |
C9—H9 | 0.9300 | C1—C2 | 1.379 (3) |
N2—O4 | 1.211 (2) | C6—H6 | 0.9300 |
N2—O5 | 1.216 (2) | C13—C12 | 1.382 (3) |
N2—C10 | 1.470 (3) | C13—H13 | 0.9300 |
N1—C7 | 1.383 (3) | C2—H2 | 0.9300 |
N1—HN1 | 0.80 (2) | C12—H12 | 0.9300 |
C10—C11 | 1.377 (3) | C14—H14A | 0.9600 |
O3—C7 | 1.204 (3) | C14—H14B | 0.9600 |
C4—C3 | 1.372 (3) | C14—H14C | 0.9600 |
C4—C5 | 1.387 (3) | ||
O1—S1—O2 | 119.71 (11) | N1—C7—C8 | 116.62 (19) |
O1—S1—N1 | 108.51 (10) | C6—C5—C4 | 120.8 (2) |
O2—S1—N1 | 103.33 (10) | C6—C5—H5 | 119.6 |
O1—S1—C1 | 109.63 (10) | C4—C5—H5 | 119.6 |
O2—S1—C1 | 108.74 (10) | C10—C11—C12 | 118.2 (2) |
N1—S1—C1 | 105.96 (9) | C10—C11—H11 | 120.9 |
C13—C8—C9 | 119.62 (18) | C12—C11—H11 | 120.9 |
C13—C8—C7 | 124.23 (18) | C6—C1—C2 | 120.7 (2) |
C9—C8—C7 | 116.14 (18) | C6—C1—S1 | 120.36 (16) |
C10—C9—C8 | 118.78 (18) | C2—C1—S1 | 118.94 (16) |
C10—C9—H9 | 120.6 | C1—C6—C5 | 119.3 (2) |
C8—C9—H9 | 120.6 | C1—C6—H6 | 120.4 |
O4—N2—O5 | 123.57 (19) | C5—C6—H6 | 120.4 |
O4—N2—C10 | 118.53 (19) | C12—C13—C8 | 120.42 (19) |
O5—N2—C10 | 117.89 (18) | C12—C13—H13 | 119.8 |
C7—N1—S1 | 123.00 (17) | C8—C13—H13 | 119.8 |
C7—N1—HN1 | 118.4 (18) | C3—C2—C1 | 119.0 (2) |
S1—N1—HN1 | 114.5 (17) | C3—C2—H2 | 120.5 |
C9—C10—C11 | 122.56 (18) | C1—C2—H2 | 120.5 |
C9—C10—N2 | 118.58 (17) | C11—C12—C13 | 120.4 (2) |
C11—C10—N2 | 118.86 (18) | C11—C12—H12 | 119.8 |
C3—C4—C5 | 118.4 (2) | C13—C12—H12 | 119.8 |
C3—C4—C14 | 121.1 (2) | C4—C14—H14A | 109.5 |
C5—C4—C14 | 120.5 (2) | C4—C14—H14B | 109.5 |
C4—C3—C2 | 121.9 (2) | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 119.0 | C4—C14—H14C | 109.5 |
C2—C3—H3 | 119.0 | H14A—C14—H14C | 109.5 |
O3—C7—N1 | 121.6 (2) | H14B—C14—H14C | 109.5 |
O3—C7—C8 | 121.82 (19) | ||
C13—C8—C9—C10 | −1.0 (3) | C14—C4—C5—C6 | 179.3 (2) |
C7—C8—C9—C10 | −179.78 (17) | C9—C10—C11—C12 | 1.7 (3) |
O1—S1—N1—C7 | 51.79 (19) | N2—C10—C11—C12 | −178.2 (2) |
O2—S1—N1—C7 | 179.85 (17) | O1—S1—C1—C6 | −23.4 (2) |
C1—S1—N1—C7 | −65.87 (19) | O2—S1—C1—C6 | −155.95 (17) |
C8—C9—C10—C11 | −0.3 (3) | N1—S1—C1—C6 | 93.55 (19) |
C8—C9—C10—N2 | 179.61 (17) | O1—S1—C1—C2 | 158.45 (17) |
O4—N2—C10—C9 | 166.6 (2) | O2—S1—C1—C2 | 25.9 (2) |
O5—N2—C10—C9 | −12.9 (3) | N1—S1—C1—C2 | −84.63 (19) |
O4—N2—C10—C11 | −13.5 (3) | C2—C1—C6—C5 | −0.1 (3) |
O5—N2—C10—C11 | 167.0 (2) | S1—C1—C6—C5 | −178.20 (18) |
C5—C4—C3—C2 | −0.3 (4) | C4—C5—C6—C1 | −0.2 (4) |
C14—C4—C3—C2 | −179.2 (2) | C9—C8—C13—C12 | 1.0 (3) |
S1—N1—C7—O3 | −4.9 (3) | C7—C8—C13—C12 | 179.6 (2) |
S1—N1—C7—C8 | 175.83 (14) | C4—C3—C2—C1 | 0.0 (4) |
C13—C8—C7—O3 | −162.5 (2) | C6—C1—C2—C3 | 0.2 (3) |
C9—C8—C7—O3 | 16.1 (3) | S1—C1—C2—C3 | 178.32 (18) |
C13—C8—C7—N1 | 16.8 (3) | C10—C11—C12—C13 | −1.7 (4) |
C9—C8—C7—N1 | −164.58 (18) | C8—C13—C12—C11 | 0.4 (4) |
C3—C4—C5—C6 | 0.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O2i | 0.80 (3) | 2.14 (3) | 2.927 (3) | 167 |
C13—H13···O2i | 0.93 | 2.59 | 3.333 (3) | 137 |
C3—H3···O4ii | 0.93 | 2.58 | 3.459 (3) | 155 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O2i | 0.80 (3) | 2.14 (3) | 2.927 (3) | 167 |
C13—H13···O2i | 0.93 | 2.59 | 3.333 (3) | 137 |
C3—H3···O4ii | 0.93 | 2.58 | 3.459 (3) | 155 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, 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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