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COMMUNICATIONS
ISSN: 2056-9890

(Phen­yl)(1-phenyl­sulfonyl-1H-indol-3-yl)methanone

aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, bDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 15 October 2010; accepted 18 October 2010; online 23 October 2010)

In the title compound, C21H15NO3S, the sulfonyl-bound phenyl ring forms a dihedral angle of 86.28 (5)° with the indole ring system. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds. The crystal packing is stabilized by weak inter­molecular C—H⋯O and C—H⋯π inter­actions.

Related literature

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15NO3S

  • Mr = 361.40

  • Triclinic, [P \overline 1]

  • a = 7.567 (1) Å

  • b = 10.571 (2) Å

  • c = 12.083 (3) Å

  • α = 66.302 (2)°

  • β = 80.740 (1)°

  • γ = 78.403 (1)°

  • V = 863.5 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 295 K

  • 0.24 × 0.22 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.952, Tmax = 0.960

  • 15638 measured reflections

  • 4276 independent reflections

  • 3187 reflections with I > 2σ(I)

  • Rint = 0.026

  • Standard reflections: 0

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.109

  • S = 1.01

  • 4276 reflections

  • 235 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O1 0.93 2.42 2.999 (2) 120
C6—H6⋯O2i 0.93 2.58 3.493 (2) 167
C7—H7⋯O2i 0.93 2.54 3.429 (2) 160
C4—H4⋯Cg1ii 0.93 2.98 3.774 (3) 144
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values of similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl rings C1—C6 and C16—C21 form the dihedral angles of 86.28 (5)° and 51.91 (5)°, respectively with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 42.16 (6)°.

The sum of the bond angles around N1 [358.53°] indicates that N1 atom is sp2 hybridized. The molecular structure is stabilized by intra molecular C—H···O hydrogen bonds and the crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (1 - x, -y, -z) distance of 3.774 (3)Å (Cg1 is the centroid of the ring defined by the atoms C16—C21)] interactions.

Related literature top

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a solution of 1-phenylsulfonyl-(1H-indol-3-yl)(phenyl)methanol (1 g, 2.75 mmol) in dry 1,2-Dichloroethane (30 ml), manganese dioxide (6 g. 68.96 mmol) was added then stirred at room temperature for 4 h and then refluxed for 3 h. Then the resulting solution was passed through celite pad and washed with DCM (2 x 30 ml). Removal of solvent followed by crystallization from methanol afforded the compound as a colourless crystal.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H. The components of the anisotropic displacement parameters in direction of the bond of C3and C4; C18 and C19 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL (Sheldrick, 2008).

Structure description top

The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values of similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl rings C1—C6 and C16—C21 form the dihedral angles of 86.28 (5)° and 51.91 (5)°, respectively with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 42.16 (6)°.

The sum of the bond angles around N1 [358.53°] indicates that N1 atom is sp2 hybridized. The molecular structure is stabilized by intra molecular C—H···O hydrogen bonds and the crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (1 - x, -y, -z) distance of 3.774 (3)Å (Cg1 is the centroid of the ring defined by the atoms C16—C21)] interactions.

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.
(Phenyl)(1-phenylsulfonyl-1H-indol-3-yl)methanone top
Crystal data top
C21H15NO3SZ = 2
Mr = 361.40F(000) = 376
Triclinic, P1Dx = 1.390 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.567 (1) ÅCell parameters from 6196 reflections
b = 10.571 (2) Åθ = 2.2–27.1°
c = 12.083 (3) ŵ = 0.21 mm1
α = 66.302 (2)°T = 295 K
β = 80.740 (1)°Block, colourless
γ = 78.403 (1)°0.24 × 0.22 × 0.20 mm
V = 863.5 (3) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
4276 independent reflections
Radiation source: fine-focus sealed tube3187 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.952, Tmax = 0.960k = 1413
15638 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1447P]
where P = (Fo2 + 2Fc2)/3
4276 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = 0.29 e Å3
Crystal data top
C21H15NO3Sγ = 78.403 (1)°
Mr = 361.40V = 863.5 (3) Å3
Triclinic, P1Z = 2
a = 7.567 (1) ÅMo Kα radiation
b = 10.571 (2) ŵ = 0.21 mm1
c = 12.083 (3) ÅT = 295 K
α = 66.302 (2)°0.24 × 0.22 × 0.20 mm
β = 80.740 (1)°
Data collection top
Bruker Kappa APEXII
diffractometer
4276 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3187 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.960Rint = 0.026
15638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0372 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.01Δρmax = 0.21 e Å3
4276 reflectionsΔρmin = 0.29 e Å3
235 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7233 (2)0.05722 (16)0.20701 (13)0.0494 (4)
C20.6154 (3)0.0869 (2)0.29978 (15)0.0648 (5)
H20.65230.13880.33600.078*
C30.4508 (3)0.0376 (2)0.33759 (18)0.0791 (5)
H30.37590.05670.39970.095*
C40.3975 (3)0.0394 (2)0.2838 (2)0.0806 (6)
H40.28660.07180.30970.097*
C50.5061 (3)0.0687 (2)0.1928 (2)0.0757 (5)
H50.46900.12150.15750.091*
C60.6701 (2)0.02074 (19)0.15289 (17)0.0615 (4)
H60.74400.04030.09060.074*
C140.80636 (19)0.40437 (16)0.04797 (13)0.0448 (3)
C130.7914 (2)0.44779 (18)0.14366 (15)0.0547 (4)
H130.83050.38730.21880.066*
C120.7164 (2)0.5838 (2)0.12251 (18)0.0641 (5)
H120.70180.61570.18530.077*
C110.6617 (3)0.6751 (2)0.00966 (19)0.0681 (5)
H110.61300.76710.00190.082*
C100.6778 (2)0.63262 (18)0.08489 (17)0.0609 (4)
H100.64120.69480.16030.073*
C90.75050 (19)0.49375 (16)0.06607 (14)0.0472 (3)
C80.7882 (2)0.41551 (16)0.14359 (13)0.0474 (3)
C70.86292 (19)0.28383 (16)0.07641 (12)0.0469 (3)
H70.89820.21130.10400.056*
C150.7413 (2)0.46868 (18)0.26928 (14)0.0546 (4)
C160.8200 (2)0.39033 (18)0.34881 (13)0.0553 (4)
C210.9990 (3)0.32957 (19)0.35204 (14)0.0634 (5)
H211.07370.32910.29780.076*
C201.0679 (3)0.2692 (2)0.43577 (17)0.0807 (6)
H201.18930.23010.43910.097*
C190.9549 (4)0.2676 (2)0.51451 (18)0.0891 (6)
H191.00000.22590.57000.107*
C180.7771 (4)0.3274 (3)0.51087 (19)0.0900 (6)
H180.70170.32660.56420.108*
C170.7103 (3)0.3879 (2)0.42929 (16)0.0742 (5)
H170.58940.42830.42750.089*
N10.87874 (17)0.27365 (13)0.04012 (10)0.0461 (3)
O10.98538 (16)0.15404 (13)0.24616 (10)0.0602 (3)
O21.04747 (14)0.03484 (12)0.10209 (10)0.0543 (3)
O30.63449 (19)0.57703 (15)0.30880 (11)0.0789 (4)
S10.92933 (5)0.12195 (4)0.15505 (3)0.04628 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0554 (8)0.0428 (8)0.0381 (7)0.0021 (7)0.0076 (6)0.0064 (6)
C20.0723 (11)0.0626 (11)0.0470 (9)0.0010 (9)0.0007 (8)0.0146 (8)
C30.0696 (12)0.0795 (14)0.0578 (11)0.0037 (10)0.0110 (9)0.0082 (9)
C40.0579 (10)0.0687 (13)0.0827 (14)0.0089 (9)0.0036 (10)0.0032 (9)
C50.0669 (11)0.0698 (13)0.0848 (14)0.0156 (10)0.0104 (10)0.0201 (11)
C60.0619 (10)0.0604 (11)0.0593 (10)0.0069 (8)0.0060 (8)0.0209 (8)
C140.0447 (7)0.0433 (8)0.0444 (7)0.0093 (6)0.0023 (6)0.0140 (6)
C130.0606 (9)0.0553 (10)0.0513 (9)0.0105 (8)0.0034 (7)0.0234 (8)
C120.0666 (10)0.0632 (12)0.0739 (12)0.0113 (9)0.0011 (9)0.0391 (10)
C110.0712 (11)0.0486 (10)0.0844 (13)0.0044 (8)0.0049 (10)0.0280 (10)
C100.0611 (10)0.0473 (9)0.0632 (10)0.0049 (8)0.0074 (8)0.0107 (8)
C90.0440 (7)0.0465 (8)0.0456 (8)0.0096 (6)0.0016 (6)0.0115 (6)
C80.0483 (8)0.0496 (9)0.0386 (7)0.0083 (6)0.0041 (6)0.0105 (6)
C70.0535 (8)0.0499 (9)0.0359 (7)0.0072 (7)0.0052 (6)0.0149 (6)
C150.0546 (8)0.0571 (10)0.0403 (8)0.0080 (7)0.0082 (7)0.0053 (7)
C160.0677 (10)0.0550 (10)0.0337 (7)0.0120 (8)0.0094 (7)0.0041 (7)
C210.0728 (11)0.0691 (12)0.0399 (8)0.0044 (9)0.0087 (8)0.0138 (8)
C200.1019 (15)0.0786 (14)0.0471 (10)0.0032 (12)0.0000 (10)0.0194 (9)
C190.1479 (17)0.0736 (14)0.0441 (9)0.0172 (13)0.0036 (12)0.0223 (10)
C180.1306 (15)0.0951 (17)0.0512 (10)0.0334 (13)0.0220 (12)0.0222 (11)
C170.0873 (13)0.0821 (14)0.0465 (9)0.0182 (11)0.0203 (9)0.0097 (9)
N10.0566 (7)0.0434 (7)0.0357 (6)0.0037 (6)0.0071 (5)0.0132 (5)
O10.0728 (7)0.0643 (7)0.0457 (6)0.0020 (6)0.0197 (5)0.0220 (5)
O20.0551 (6)0.0540 (7)0.0498 (6)0.0039 (5)0.0072 (5)0.0205 (5)
O30.0817 (9)0.0791 (9)0.0539 (7)0.0174 (7)0.0184 (6)0.0119 (7)
S10.0526 (2)0.0470 (2)0.03579 (19)0.00011 (16)0.00991 (15)0.01356 (15)
Geometric parameters (Å, º) top
C1—C21.381 (2)C10—H100.9300
C1—C61.386 (2)C9—C81.444 (2)
C1—S11.7498 (17)C8—C71.356 (2)
C2—C31.384 (3)C8—C151.468 (2)
C2—H20.9300C7—N11.3913 (18)
C3—C41.375 (3)C7—H70.9300
C3—H30.9300C15—O31.227 (2)
C4—C51.364 (3)C15—C161.490 (2)
C4—H40.9300C16—C211.379 (2)
C5—C61.376 (3)C16—C171.387 (2)
C5—H50.9300C21—C201.385 (3)
C6—H60.9300C21—H210.9300
C14—C131.387 (2)C20—C191.385 (3)
C14—C91.397 (2)C20—H200.9300
C14—N11.4152 (19)C19—C181.369 (3)
C13—C121.370 (2)C19—H190.9300
C13—H130.9300C18—C171.361 (3)
C12—C111.388 (3)C18—H180.9300
C12—H120.9300C17—H170.9300
C11—C101.366 (3)N1—S11.6677 (12)
C11—H110.9300O1—S11.4195 (11)
C10—C91.399 (2)O2—S11.4195 (11)
C2—C1—C6121.26 (17)C7—C8—C9107.38 (13)
C2—C1—S1119.33 (14)C7—C8—C15127.21 (15)
C6—C1—S1119.39 (12)C9—C8—C15125.29 (15)
C1—C2—C3118.46 (19)C8—C7—N1109.68 (13)
C1—C2—H2120.8C8—C7—H7125.2
C3—C2—H2120.8N1—C7—H7125.2
C4—C3—C2120.39 (18)O3—C15—C8119.99 (16)
C4—C3—H3119.8O3—C15—C16119.61 (14)
C2—C3—H3119.8C8—C15—C16120.39 (14)
C5—C4—C3120.5 (2)C21—C16—C17118.93 (18)
C5—C4—H4119.7C21—C16—C15123.05 (15)
C3—C4—H4119.7C17—C16—C15117.84 (17)
C4—C5—C6120.5 (2)C16—C21—C20120.24 (18)
C4—C5—H5119.8C16—C21—H21119.9
C6—C5—H5119.8C20—C21—H21119.9
C5—C6—C1118.91 (18)C21—C20—C19119.5 (2)
C5—C6—H6120.5C21—C20—H20120.2
C1—C6—H6120.5C19—C20—H20120.2
C13—C14—C9122.50 (15)C18—C19—C20120.2 (2)
C13—C14—N1130.70 (14)C18—C19—H19119.9
C9—C14—N1106.78 (13)C20—C19—H19119.9
C12—C13—C14117.03 (16)C17—C18—C19120.1 (2)
C12—C13—H13121.5C17—C18—H18120.0
C14—C13—H13121.5C19—C18—H18120.0
C13—C12—C11121.58 (17)C18—C17—C16121.0 (2)
C13—C12—H12119.2C18—C17—H17119.5
C11—C12—H12119.2C16—C17—H17119.5
C10—C11—C12121.37 (17)C7—N1—C14108.35 (12)
C10—C11—H11119.3C7—N1—S1123.27 (10)
C12—C11—H11119.3C14—N1—S1126.91 (10)
C11—C10—C9118.68 (17)O2—S1—O1120.91 (7)
C11—C10—H10120.7O2—S1—N1105.43 (7)
C9—C10—H10120.7O1—S1—N1106.66 (7)
C14—C9—C10118.82 (15)O2—S1—C1108.92 (7)
C14—C9—C8107.78 (14)O1—S1—C1109.22 (7)
C10—C9—C8133.37 (15)N1—S1—C1104.41 (7)
C6—C1—C2—C30.4 (3)C8—C15—C16—C2142.0 (2)
S1—C1—C2—C3178.44 (13)O3—C15—C16—C1735.9 (2)
C1—C2—C3—C40.2 (3)C8—C15—C16—C17142.89 (16)
C2—C3—C4—C50.2 (3)C17—C16—C21—C201.0 (3)
C3—C4—C5—C60.5 (3)C15—C16—C21—C20174.08 (16)
C4—C5—C6—C10.3 (3)C16—C21—C20—C191.4 (3)
C2—C1—C6—C50.2 (3)C21—C20—C19—C181.1 (3)
S1—C1—C6—C5178.69 (14)C20—C19—C18—C170.4 (4)
C9—C14—C13—C120.7 (2)C19—C18—C17—C160.0 (3)
N1—C14—C13—C12178.95 (15)C21—C16—C17—C180.3 (3)
C14—C13—C12—C111.5 (3)C15—C16—C17—C18175.06 (18)
C13—C12—C11—C101.0 (3)C8—C7—N1—C141.51 (16)
C12—C11—C10—C90.3 (3)C8—C7—N1—S1168.55 (10)
C13—C14—C9—C100.5 (2)C13—C14—N1—C7179.63 (15)
N1—C14—C9—C10178.11 (13)C9—C14—N1—C71.22 (16)
C13—C14—C9—C8179.08 (14)C13—C14—N1—S113.9 (2)
N1—C14—C9—C80.51 (16)C9—C14—N1—S1167.65 (10)
C11—C10—C9—C141.0 (2)C7—N1—S1—O233.46 (13)
C11—C10—C9—C8179.16 (16)C14—N1—S1—O2161.98 (12)
C14—C9—C8—C70.40 (16)C7—N1—S1—O1163.18 (12)
C10—C9—C8—C7178.74 (17)C14—N1—S1—O132.27 (14)
C14—C9—C8—C15176.58 (14)C7—N1—S1—C181.25 (13)
C10—C9—C8—C155.1 (3)C14—N1—S1—C183.30 (13)
C9—C8—C7—N11.18 (17)C2—C1—S1—O2155.20 (12)
C15—C8—C7—N1177.26 (14)C6—C1—S1—O225.92 (15)
C7—C8—C15—O3161.36 (17)C2—C1—S1—O121.21 (15)
C9—C8—C15—O314.1 (2)C6—C1—S1—O1159.91 (13)
C7—C8—C15—C1617.5 (2)C2—C1—S1—N192.56 (13)
C9—C8—C15—C16167.13 (14)C6—C1—S1—N186.32 (14)
O3—C15—C16—C21139.19 (18)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.592.934 (2)103
C10—H10···O30.932.573.068 (3)114
C13—H13···O10.932.422.999 (2)120
C6—H6···O2i0.932.583.493 (2)167
C7—H7···O2i0.932.543.429 (2)160
C4—H4···Cg1ii0.932.983.774 (3)144
Symmetry codes: (i) x+2, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC21H15NO3S
Mr361.40
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.567 (1), 10.571 (2), 12.083 (3)
α, β, γ (°)66.302 (2), 80.740 (1), 78.403 (1)
V3)863.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.24 × 0.22 × 0.20
Data collection
DiffractometerBruker Kappa APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.952, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
15638, 4276, 3187
Rint0.026
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.109, 1.01
No. of reflections4276
No. of parameters235
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.592.934 (2)103
C10—H10···O30.932.573.068 (3)114
C13—H13···O10.932.422.999 (2)120
C6—H6···O2i0.932.583.493 (2)167
C7—H7···O2i0.932.543.429 (2)160
C4—H4···Cg1ii0.932.983.774 (3)144
Symmetry codes: (i) x+2, y, z; (ii) x+1, y, z.
 

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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