6-Phenyl­benzo[d]naphtho­[2,3-b]thio­phene

Silambarasan, V.; Srinivasan, T.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536812049471

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o36

https://doi.org/10.1107/S1600536812049471

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6-Phenylbenzo[d]naphtho[2,3-b]thiophene

V. Silambarasan,^a T. Srinivasan,^a R. Sivasakthikumaran,^b A. K. Mohanakrishnan ^b and D. Velmurugan ^a ^*

^aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 19 November 2012; accepted 3 December 2012; online 8 December 2012)

In the title compound, C₂₂H₁₄S, the r.m.s. deviation from the mean plane of the four-fused-ring naphthothiophene unit is 0.056 Å. The dihedral angle between the naphthothiophene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C—H⋯π and π–π stacking [minimum centroid–centroid separation = 3.7466 (10) Å] interactions are observed, which together lead to (010) sheets.

Related literature

For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010 ).

Experimental

Crystal data

C₂₂H₁₄S
M_r = 310.40
Orthorhombic, P c c n
a = 12.6752 (10) Å
b = 28.578 (2) Å
c = 8.5659 (6) Å
V = 3102.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
16518 measured reflections
3855 independent reflections
2892 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.03
3855 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg2ⁱ	0.93	2.94	3.8138 (19)	158
C13—H13⋯Cg3ⁱ	0.93	2.64	3.5399 (17)	163
Symmetry code: (i) $[-x-{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049471/hb6995sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049471/hb6995Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049471/hb6995Isup3.cml

checkCIF report

Comment top

Some benzo[b]thiophene derivatives show significant antimicrobial and anti-inflammatory activities (Isloora et al., 2010). As part of our own studies in this area, an X-ray study of the title compound was carried out.

Fig. 1 shows the ORTEP representation of the molecular structure of the title compound with atoms at the 30% probability level. The naphthothiophene moiety is almost planar with an r.m.s. deviation of fitted atoms = -0.0065 (1)°. The dihedral angle between the naphthothiophene plane and the attached benzene [C17—C22] ring is 67.24 (6)°. The thiophene ring is almost planar, with maximum deviation of 0.014 (1) Å.

In the crystal, C—H···π interactions occur (Table 1).

Related literature top

For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010).

Experimental top

The benzo[b]thiophen-3-yl(2-(phenyl(pivaloyloxy)methyl)phenyl) methyl pivalate (0.73 g, 1.60 mmol) upon interaction with ZnBr2 (0.02 g, 0.13 mmol) followed by removal of solvent and column chromatographic purification (silica gel; hexane-ethyl acetate, 99:1) gave the compound as a colorless solid (0.50 g, 72%). Colourless blocks were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

In the crystal, C—H···π interactions occur (Table 1).

For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The π···π and C—H···π interactions (dotted lines) in the title compound. Cg1, Cg2 and Cg3 are the centroids of the S1/C1/C6/C7/C8, C1—C6, C7—C12 rings. [Symmetry code: (i) 1 - x,-y,2 - z; (ii) 1/2 - x,y,1/2 + z].

6-Phenylbenzo[d]naphtho[2,3-b]thiophene top

Crystal data top

C₂₂H₁₄S	F(000) = 1296
M_r = 310.40	D_x = 1.329 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3855 reflections
a = 12.6752 (10) Å	θ = 1.8–28.4°
b = 28.578 (2) Å	µ = 0.21 mm⁻¹
c = 8.5659 (6) Å	T = 293 K
V = 3102.8 (4) Å³	Block, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	2892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 28.4°, θ_min = 1.8°
ω and φ scans	h = −16→16
16518 measured reflections	k = −34→38
3855 independent reflections	l = −9→11

Refinement top

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) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0571P)² + 0.6864P] where P = (F_o² + 2F_c²)/3
3855 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₁₄S	V = 3102.8 (4) Å³
M_r = 310.40	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 12.6752 (10) Å	µ = 0.21 mm⁻¹
b = 28.578 (2) Å	T = 293 K
c = 8.5659 (6) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	2892 reflections with I > 2σ(I)
16518 measured reflections	R_int = 0.031
3855 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
3855 reflections	Δρ_min = −0.24 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.49436 (3)	0.039709 (15)	0.71196 (5)	0.04701 (14)
C11	0.34912 (11)	0.12197 (5)	1.10829 (17)	0.0367 (3)
C10	0.41403 (11)	0.14729 (5)	1.00101 (17)	0.0361 (3)
C17	0.52550 (12)	0.14890 (5)	0.75491 (18)	0.0375 (3)
C7	0.37407 (11)	0.05119 (5)	0.95979 (18)	0.0376 (3)
C9	0.46095 (11)	0.12338 (5)	0.87264 (17)	0.0361 (3)
C13	0.30387 (12)	0.14611 (6)	1.23609 (19)	0.0444 (4)
H13	0.2633	0.1297	1.3080	0.053*
C8	0.44145 (11)	0.07613 (5)	0.85662 (17)	0.0369 (3)
C22	0.62230 (13)	0.16834 (6)	0.7927 (2)	0.0471 (4)
H22	0.6492	0.1648	0.8930	0.057*
C1	0.42526 (12)	−0.00859 (5)	0.78516 (19)	0.0411 (3)
C6	0.36343 (12)	0.00252 (5)	0.91445 (18)	0.0388 (3)
C12	0.32950 (12)	0.07416 (5)	1.08341 (19)	0.0397 (3)
H12	0.2857	0.0579	1.1517	0.048*
C16	0.42662 (13)	0.19611 (6)	1.0261 (2)	0.0437 (4)
H16	0.4677	0.2134	0.9572	0.052*
C18	0.48824 (13)	0.15417 (6)	0.6039 (2)	0.0457 (4)
H18	0.4244	0.1406	0.5755	0.055*
C19	0.54498 (15)	0.17947 (7)	0.4950 (2)	0.0533 (4)
H19	0.5189	0.1832	0.3943	0.064*
C5	0.30009 (14)	−0.03191 (6)	0.9809 (2)	0.0491 (4)
H5	0.2582	−0.0250	1.0670	0.059*
C20	0.63982 (15)	0.19908 (6)	0.5357 (2)	0.0528 (4)
H20	0.6774	0.2166	0.4629	0.063*
C15	0.37981 (14)	0.21805 (6)	1.1489 (2)	0.0499 (4)
H15	0.3886	0.2501	1.1620	0.060*
C2	0.42771 (15)	−0.05383 (6)	0.7253 (2)	0.0493 (4)
H2	0.4712	−0.0614	0.6415	0.059*
C21	0.67926 (14)	0.19303 (6)	0.6823 (2)	0.0536 (4)
H21	0.7447	0.2056	0.7083	0.064*
C3	0.36430 (15)	−0.08691 (6)	0.7931 (2)	0.0539 (5)
H3	0.3645	−0.1173	0.7539	0.065*
C4	0.29989 (15)	−0.07614 (6)	0.9188 (2)	0.0554 (5)
H4	0.2563	−0.0990	0.9613	0.066*
C14	0.31846 (14)	0.19275 (6)	1.2558 (2)	0.0501 (4)
H14	0.2877	0.2080	1.3403	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0557 (3)	0.0449 (2)	0.0404 (3)	−0.00271 (18)	0.01194 (18)	−0.00246 (18)
C11	0.0346 (7)	0.0416 (8)	0.0341 (8)	0.0018 (6)	−0.0010 (6)	0.0011 (6)
C10	0.0347 (7)	0.0395 (8)	0.0340 (8)	0.0009 (6)	−0.0037 (6)	0.0022 (6)
C17	0.0415 (8)	0.0346 (8)	0.0365 (8)	0.0008 (6)	0.0039 (6)	0.0026 (6)
C7	0.0372 (7)	0.0384 (8)	0.0371 (8)	−0.0013 (6)	−0.0001 (6)	0.0039 (6)
C9	0.0355 (7)	0.0395 (8)	0.0333 (8)	−0.0024 (6)	−0.0016 (6)	0.0037 (6)
C13	0.0418 (8)	0.0510 (10)	0.0404 (9)	0.0017 (7)	0.0051 (7)	−0.0001 (7)
C8	0.0382 (7)	0.0394 (8)	0.0332 (8)	0.0001 (6)	0.0013 (6)	0.0010 (6)
C22	0.0508 (9)	0.0483 (9)	0.0423 (9)	−0.0087 (7)	−0.0026 (7)	0.0066 (8)
C1	0.0437 (8)	0.0392 (8)	0.0403 (9)	0.0014 (6)	−0.0038 (7)	0.0014 (7)
C6	0.0416 (8)	0.0356 (8)	0.0391 (8)	0.0010 (6)	−0.0025 (6)	0.0028 (6)
C12	0.0392 (7)	0.0410 (8)	0.0390 (8)	−0.0020 (6)	0.0050 (6)	0.0055 (7)
C16	0.0485 (8)	0.0392 (8)	0.0435 (9)	−0.0025 (7)	−0.0016 (7)	0.0033 (7)
C18	0.0454 (8)	0.0521 (10)	0.0397 (9)	−0.0004 (7)	0.0008 (7)	0.0042 (7)
C19	0.0608 (10)	0.0604 (11)	0.0386 (9)	0.0084 (9)	0.0052 (8)	0.0102 (8)
C5	0.0555 (10)	0.0402 (9)	0.0516 (10)	−0.0024 (7)	0.0069 (8)	0.0044 (7)
C20	0.0602 (10)	0.0450 (9)	0.0533 (11)	−0.0006 (8)	0.0188 (9)	0.0111 (8)
C15	0.0582 (10)	0.0401 (9)	0.0515 (10)	0.0023 (7)	−0.0028 (8)	−0.0043 (8)
C2	0.0580 (10)	0.0445 (9)	0.0454 (10)	0.0083 (8)	−0.0041 (8)	−0.0043 (8)
C21	0.0518 (9)	0.0504 (10)	0.0585 (11)	−0.0133 (8)	0.0052 (8)	0.0055 (9)
C3	0.0692 (11)	0.0344 (8)	0.0580 (11)	0.0036 (8)	−0.0092 (9)	−0.0027 (8)
C4	0.0653 (11)	0.0384 (9)	0.0625 (12)	−0.0048 (8)	0.0017 (9)	0.0067 (8)
C14	0.0538 (10)	0.0511 (10)	0.0455 (10)	0.0071 (8)	0.0040 (8)	−0.0098 (8)

Geometric parameters (Å, º) top

S1—C1	1.7508 (16)	C12—H12	0.9300
S1—C8	1.7518 (15)	C16—C15	1.360 (2)
C11—C12	1.405 (2)	C16—H16	0.9300
C11—C13	1.415 (2)	C18—C19	1.382 (2)
C11—C10	1.430 (2)	C18—H18	0.9300
C10—C16	1.421 (2)	C19—C20	1.371 (3)
C10—C9	1.425 (2)	C19—H19	0.9300
C17—C22	1.385 (2)	C5—C4	1.372 (2)
C17—C18	1.385 (2)	C5—H5	0.9300
C17—C9	1.489 (2)	C20—C21	1.363 (3)
C7—C12	1.368 (2)	C20—H20	0.9300
C7—C8	1.421 (2)	C15—C14	1.402 (2)
C7—C6	1.450 (2)	C15—H15	0.9300
C9—C8	1.380 (2)	C2—C3	1.370 (3)
C13—C14	1.356 (2)	C2—H2	0.9300
C13—H13	0.9300	C21—H21	0.9300
C22—C21	1.383 (2)	C3—C4	1.386 (3)
C22—H22	0.9300	C3—H3	0.9300
C1—C2	1.391 (2)	C4—H4	0.9300
C1—C6	1.393 (2)	C14—H14	0.9300
C6—C5	1.392 (2)

C1—S1—C8	91.35 (7)	C15—C16—C10	121.39 (15)
C12—C11—C13	121.30 (14)	C15—C16—H16	119.3
C12—C11—C10	119.76 (13)	C10—C16—H16	119.3
C13—C11—C10	118.92 (14)	C19—C18—C17	120.63 (16)
C16—C10—C9	122.76 (14)	C19—C18—H18	119.7
C16—C10—C11	117.65 (14)	C17—C18—H18	119.7
C9—C10—C11	119.57 (13)	C20—C19—C18	119.93 (17)
C22—C17—C18	118.47 (14)	C20—C19—H19	120.0
C22—C17—C9	121.64 (14)	C18—C19—H19	120.0
C18—C17—C9	119.89 (14)	C4—C5—C6	119.59 (17)
C12—C7—C8	119.28 (14)	C4—C5—H5	120.2
C12—C7—C6	128.98 (14)	C6—C5—H5	120.2
C8—C7—C6	111.74 (13)	C21—C20—C19	120.25 (16)
C8—C9—C10	118.13 (13)	C21—C20—H20	119.9
C8—C9—C17	120.69 (14)	C19—C20—H20	119.9
C10—C9—C17	121.14 (13)	C16—C15—C14	120.59 (16)
C14—C13—C11	121.33 (16)	C16—C15—H15	119.7
C14—C13—H13	119.3	C14—C15—H15	119.7
C11—C13—H13	119.3	C3—C2—C1	118.14 (17)
C9—C8—C7	122.47 (14)	C3—C2—H2	120.9
C9—C8—S1	125.69 (12)	C1—C2—H2	120.9
C7—C8—S1	111.84 (11)	C20—C21—C22	120.21 (16)
C21—C22—C17	120.47 (16)	C20—C21—H21	119.9
C21—C22—H22	119.8	C22—C21—H21	119.9
C17—C22—H22	119.8	C2—C3—C4	121.47 (16)
C2—C1—C6	121.15 (15)	C2—C3—H3	119.3
C2—C1—S1	126.11 (13)	C4—C3—H3	119.3
C6—C1—S1	112.73 (12)	C5—C4—C3	120.33 (17)
C5—C6—C1	119.26 (15)	C5—C4—H4	119.8
C5—C6—C7	128.46 (15)	C3—C4—H4	119.8
C1—C6—C7	112.27 (13)	C13—C14—C15	120.07 (16)
C7—C12—C11	120.72 (14)	C13—C14—H14	120.0
C7—C12—H12	119.6	C15—C14—H14	120.0
C11—C12—H12	119.6

C12—C11—C10—C16	176.46 (14)	S1—C1—C6—C5	177.03 (13)
C13—C11—C10—C16	−2.1 (2)	C2—C1—C6—C7	178.72 (14)
C12—C11—C10—C9	−2.0 (2)	S1—C1—C6—C7	−1.81 (17)
C13—C11—C10—C9	179.41 (13)	C12—C7—C6—C5	4.2 (3)
C16—C10—C9—C8	−178.29 (14)	C8—C7—C6—C5	−176.05 (16)
C11—C10—C9—C8	0.1 (2)	C12—C7—C6—C1	−177.08 (15)
C16—C10—C9—C17	−0.9 (2)	C8—C7—C6—C1	2.66 (19)
C11—C10—C9—C17	177.53 (13)	C8—C7—C12—C11	0.5 (2)
C22—C17—C9—C8	−114.77 (18)	C6—C7—C12—C11	−179.82 (15)
C18—C17—C9—C8	66.1 (2)	C13—C11—C12—C7	−179.73 (14)
C22—C17—C9—C10	67.9 (2)	C10—C11—C12—C7	1.7 (2)
C18—C17—C9—C10	−111.22 (17)	C9—C10—C16—C15	179.23 (15)
C12—C11—C13—C14	−176.64 (16)	C11—C10—C16—C15	0.8 (2)
C10—C11—C13—C14	1.9 (2)	C22—C17—C18—C19	−2.0 (2)
C10—C9—C8—C7	2.1 (2)	C9—C17—C18—C19	177.19 (16)
C17—C9—C8—C7	−175.29 (14)	C17—C18—C19—C20	0.9 (3)
C10—C9—C8—S1	−177.76 (11)	C1—C6—C5—C4	0.3 (3)
C17—C9—C8—S1	4.8 (2)	C7—C6—C5—C4	178.93 (16)
C12—C7—C8—C9	−2.5 (2)	C18—C19—C20—C21	1.1 (3)
C6—C7—C8—C9	177.76 (14)	C10—C16—C15—C14	0.8 (3)
C12—C7—C8—S1	177.44 (12)	C6—C1—C2—C3	2.6 (2)
C6—C7—C8—S1	−2.33 (16)	S1—C1—C2—C3	−176.83 (13)
C1—S1—C8—C9	−178.97 (14)	C19—C20—C21—C22	−2.1 (3)
C1—S1—C8—C7	1.12 (12)	C17—C22—C21—C20	1.0 (3)
C18—C17—C22—C21	1.0 (3)	C1—C2—C3—C4	−0.6 (3)
C9—C17—C22—C21	−178.11 (16)	C6—C5—C4—C3	1.6 (3)
C8—S1—C1—C2	179.84 (15)	C2—C3—C4—C5	−1.5 (3)
C8—S1—C1—C6	0.41 (12)	C11—C13—C14—C15	−0.3 (3)
C2—C1—C6—C5	−2.4 (2)	C16—C15—C14—C13	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg2ⁱ	0.93	2.94	3.8138 (19)	158
C13—H13···Cg3ⁱ	0.93	2.64	3.5399 (17)	163

Symmetry code: (i) −x−1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄S
M_r	310.40
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	12.6752 (10), 28.578 (2), 8.5659 (6)
V (Å³)	3102.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16518, 3855, 2892
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.03
No. of reflections	3855
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg2ⁱ	0.93	2.94	3.8138 (19)	158
C13—H13···Cg3ⁱ	0.93	2.64	3.5399 (17)	163

Symmetry code: (i) −x−1/2, y, z−1/2.

Acknowledgements

VS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, and the UGC SAP for the facilities to the department.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825–830. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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