Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o807-o808
https://doi.org/10.1107/S2056989015018022

Crystal structure of 2-amino-N-(2-fluoro­phen­yl)-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carboxamide

K. Chandra Kumar,a V. Umesh,b T. K. Madhura,c B. M. Rajesha and Chandrad*

aDepartment of Engineering Physics, HKBK College of Engineering, Bengaluru 560 045, India, bDepartment of Physics, JSS College for Women (Autonomous), Saraswathipuram, Mysuru 570 009, India, cDepartment of Physics, Atria Institute of Technology, Bengaluru 560 024, India, and dDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: mychandru.10@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 24 August 2015; accepted 26 September 2015; online 3 October 2015)

In the title compound, C15H15FN2OS, the dihedral angle between the planes of the benzo­thio­phene ring system and the fluoro­benzene ring is 3.74 (14)°. The six-membered ring of the benzo­thio­phene moiety adopts a half-chair conformation. The mol­ecular conformation is consolidated by intra­molecular N—H⋯F and N—H⋯O hydrogen bonds. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, generating C(6) [001] chains.

CCDC reference: 1045467

Similar articles

1. Related literature

For background to thio­phene derivatives, see: Bonini et al. (2005[Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron, 61, 6580-6589.]); Brault et al. (2005[Brault, L., Migianu, E., Néguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-763.]); Isloor et al. (2010[Isloor, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825-830.]). For inter­molecular inter­actions involving F atoms, see: Choudhury et al. (2004[Choudhury, A. R., Nagarajan, K. & Guru Row, T. N. (2004). Acta Cryst. C60, o644-o647.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H15FN2OS

  • Mr = 290.36

  • Monoclinic C c

  • a = 11.213 (13) Å

  • b = 14.231 (17) Å

  • c = 9.582 (15) Å

  • β = 116.76 (3)°

  • V = 1365 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

2.2. Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • 5264 measured reflections

  • 2577 independent reflections

  • 2363 reflections with I > 2σ(I)

  • Rint = 0.029

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.081

  • S = 1.84

  • 2577 reflections

  • 182 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Absolute structure parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N8—H9A⋯F7 0.86 2.26 2.643 (5) 107
N16—H15C⋯O10 0.86 2.16 2.733 (5) 124
N16—H15D⋯O10i 0.86 2.25 2.986 (6) 143
Symmetry code: (i) [x, -y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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

CCDC reference: 1045467

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015018022/hb7493sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018022/hb7493Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015018022/hb7493Isup3.cml

checkCIF report


Comment top

Thiophene nucleus has been established as a potential entity in the largely growing chemical world of heterocyclic compounds possessing promising pharmacological characteristics such as anti-HIV PR inhibitors (Bonini et al., 2005) and anti-breast cancer (Brault et al., 2005) activities. Particularly, benzothiophene derivative shows significant antimicrobial and anti- inflammatory activities (Isloora et al., 2010). In addition structures containing fluorine atoms plays a major role in intermolecular interactions (Choudhury et al., 2004). The title compound was prepared and characterized by single-crystal X-ray diffraction studies.

In the molecular structure of the title compound (Fig. 1), the dihedral angle between the flurobenzene (C1–C2–C3–C4–C5–C6) and benzothiophene (C11–C12–C13–S14–C15–C17–C18–C19–C20) ring is 3.74 (14)°. The benzothiophene moiety adopts a half chair conformation conformation with puckering parameter Q = 0.475 (3) Å and φ = 215.4 (5)°, and the maximum deviation found on the puckered atom at C18 is 0.372 (4) Å. The carboximidamide unit is in anti-periplanar conformation with respect to the benzothiophene moiety, as indicated by the torsion angle value of 161.9 (3)° (N8–C9–C11–C15). The crystal structure features intermolecular N—H···O hydrogen bonds. The packing diagram of the molecule viewed down the a axis as shown in Fig. 2.

Related literature top

For background to thiophene derivatives, see: Bonini et al. (2005); Brault et al. (2005); Isloor et al. (2010). For intermolecular interactions involving F atoms, see: Choudhury et al. ( 2004).

Experimental top

Cyclohexanone (1 equiv.), 2-cyano-N-(2-fluorophenyl) acetamide (1.1 equiv.), elemental sulfur (1.2 equiv.), diethylamine (0.8 equiv.) was taken in ethanol and mixed thoroughly in a microwave tube. The tube was sealed and irradiated at 325 K for 15 min. After cooling ethyl acetate was added to the reaction mixture and solid residue was removed by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain yellow block shaped crystals.

Refinement top

H atoms were placed at idealized positions and allowed to ride on their parent atoms with N–H distance is equal to 0.86 and C–H distances in the range of 0.93 to 0.97 Å; Uiso(H) = 1.2–1.5Ueq(carrier atom) for all H atoms.

Structure description top

Thiophene nucleus has been established as a potential entity in the largely growing chemical world of heterocyclic compounds possessing promising pharmacological characteristics such as anti-HIV PR inhibitors (Bonini et al., 2005) and anti-breast cancer (Brault et al., 2005) activities. Particularly, benzothiophene derivative shows significant antimicrobial and anti- inflammatory activities (Isloora et al., 2010). In addition structures containing fluorine atoms plays a major role in intermolecular interactions (Choudhury et al., 2004). The title compound was prepared and characterized by single-crystal X-ray diffraction studies.

In the molecular structure of the title compound (Fig. 1), the dihedral angle between the flurobenzene (C1–C2–C3–C4–C5–C6) and benzothiophene (C11–C12–C13–S14–C15–C17–C18–C19–C20) ring is 3.74 (14)°. The benzothiophene moiety adopts a half chair conformation conformation with puckering parameter Q = 0.475 (3) Å and φ = 215.4 (5)°, and the maximum deviation found on the puckered atom at C18 is 0.372 (4) Å. The carboximidamide unit is in anti-periplanar conformation with respect to the benzothiophene moiety, as indicated by the torsion angle value of 161.9 (3)° (N8–C9–C11–C15). The crystal structure features intermolecular N—H···O hydrogen bonds. The packing diagram of the molecule viewed down the a axis as shown in Fig. 2.

For background to thiophene derivatives, see: Bonini et al. (2005); Brault et al. (2005); Isloor et al. (2010). For intermolecular interactions involving F atoms, see: Choudhury et al. ( 2004).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Perspective diagram of the molecule with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the molecule viewed down the 'a' axis.
2-Amino-N-(2-fluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide top
Crystal data top
C15H15FN2OSF(000) = 608
Mr = 290.36Dx = 1.413 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2577 reflections
a = 11.213 (13) Åθ = 2.5–26.4°
b = 14.231 (17) ŵ = 0.25 mm−1
c = 9.582 (15) ÅT = 293 K
β = 116.76 (3)°Bolck, yellow
V = 1365 (3) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		Rint = 0.029
ω and φ scansθmax = 26.4°, θmin = 2.5°
5264 measured reflectionsh = −13→14
2577 independent reflectionsk = −17→17
2363 reflections with I > 2σ(I)l = −11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.010P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.84(Δ/σ)max < 0.001
2577 reflectionsΔρmax = 0.20 e Å−3
182 parametersΔρmin = −0.29 e Å−3
2 restraintsAbsolute structure: Flack (1983), ??? Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (7)
Crystal data top
C15H15FN2OSV = 1365 (3) Å3
Mr = 290.36Z = 4
Monoclinic, CcMo Kα radiation
a = 11.213 (13) ŵ = 0.25 mm−1
b = 14.231 (17) ÅT = 293 K
c = 9.582 (15) Å0.30 × 0.25 × 0.20 mm
β = 116.76 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2363 reflections with I > 2σ(I)
5264 measured reflectionsRint = 0.029
2577 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.081Δρmax = 0.20 e Å−3
S = 1.84Δρmin = −0.29 e Å−3
2577 reflectionsAbsolute structure: Flack (1983), ??? Friedel pairs
182 parametersAbsolute structure parameter: 0.06 (7)
2 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
S140.42139 (7)0.13494 (4)1.08277 (7)0.0586 (3)
F70.17969 (19)0.42740 (10)0.4264 (2)0.0746 (6)
O100.2917 (2)0.10081 (11)0.56571 (19)0.0568 (7)
N80.2299 (2)0.25423 (14)0.5376 (2)0.0503 (7)
N160.3503 (2)0.01559 (15)0.8447 (3)0.0674 (9)
C10.1812 (2)0.26650 (18)0.3762 (3)0.0466 (9)
C20.1530 (3)0.1953 (2)0.2671 (3)0.0588 (10)
C30.1087 (4)0.2175 (3)0.1106 (3)0.0727 (11)
C40.0865 (3)0.3097 (3)0.0601 (4)0.0735 (13)
C50.1109 (3)0.3807 (2)0.1661 (3)0.0643 (11)
C60.1566 (3)0.35800 (18)0.3201 (3)0.0519 (9)
C90.2880 (3)0.17625 (17)0.6279 (3)0.0444 (9)
C110.3397 (2)0.18699 (17)0.7955 (3)0.0423 (8)
C120.3705 (3)0.27223 (17)0.8901 (3)0.0422 (8)
C130.4142 (3)0.25543 (17)1.0436 (3)0.0478 (8)
C150.3637 (3)0.10698 (17)0.8869 (3)0.0483 (9)
C170.3638 (3)0.37266 (16)0.8342 (3)0.0497 (9)
C180.4470 (3)0.43925 (17)0.9684 (3)0.0575 (10)
C190.4211 (4)0.42420 (18)1.1078 (3)0.0665 (11)
C200.4583 (3)0.32519 (19)1.1743 (3)0.0583 (10)
H2A0.163700.132800.298800.0710*
H3A0.093700.169600.038600.0870*
H4A0.055200.32350−0.045500.0880*
H5A0.096700.443000.133700.0770*
H9A0.222200.302200.587400.0600*
H15C0.323300.000500.748200.0810*
H15D0.36900−0.027600.914200.0810*
H18A0.554300.320901.237600.0700*
H18B0.415700.311401.240400.0700*
H20A0.327200.435101.077400.0800*
H20B0.472400.469501.188200.0800*
H21A0.541100.429200.998800.0690*
H21B0.425700.503700.932900.0690*
H22A0.271500.393400.785600.0600*
H22B0.396100.375000.755900.0600*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S140.0914 (6)0.0458 (4)0.0421 (4)0.0089 (4)0.0332 (4)0.0085 (3)
F70.1052 (14)0.0470 (9)0.0552 (10)−0.0004 (8)0.0217 (9)−0.0020 (7)
O100.0853 (14)0.0416 (10)0.0432 (10)0.0028 (9)0.0286 (10)−0.0026 (8)
N80.0726 (15)0.0413 (11)0.0362 (11)0.0066 (10)0.0239 (11)−0.0015 (8)
N160.116 (2)0.0397 (13)0.0496 (13)0.0007 (12)0.0400 (13)0.0038 (10)
C10.0467 (15)0.0481 (16)0.0397 (15)0.0014 (11)0.0147 (13)0.0030 (11)
C20.073 (2)0.0556 (17)0.0419 (15)0.0064 (14)0.0206 (15)0.0020 (12)
C30.087 (2)0.080 (2)0.0370 (15)0.0112 (17)0.0154 (15)−0.0070 (15)
C40.095 (3)0.083 (2)0.0342 (15)0.0095 (19)0.0217 (16)0.0113 (14)
C50.070 (2)0.0614 (18)0.0486 (18)0.0004 (14)0.0153 (15)0.0137 (13)
C60.0546 (17)0.0487 (16)0.0459 (16)−0.0034 (12)0.0170 (13)−0.0001 (12)
C90.0539 (17)0.0385 (13)0.0445 (14)−0.0016 (12)0.0255 (13)0.0000 (11)
C110.0541 (17)0.0391 (13)0.0377 (13)0.0027 (11)0.0241 (13)0.0029 (10)
C120.0534 (16)0.0389 (13)0.0379 (15)0.0012 (11)0.0238 (13)0.0015 (10)
C130.0616 (16)0.0414 (13)0.0426 (15)0.0068 (12)0.0255 (14)0.0037 (10)
C150.0671 (19)0.0425 (14)0.0408 (15)0.0012 (12)0.0293 (14)0.0005 (11)
C170.0697 (17)0.0404 (14)0.0431 (13)0.0014 (12)0.0291 (12)0.0014 (10)
C180.075 (2)0.0433 (14)0.0542 (16)−0.0033 (13)0.0292 (15)−0.0045 (12)
C190.100 (2)0.0474 (15)0.059 (2)0.0027 (16)0.0418 (19)−0.0082 (14)
C200.079 (2)0.0536 (16)0.0434 (16)0.0055 (14)0.0286 (15)−0.0018 (12)
Geometric parameters (Å, º) top
S14—C131.749 (4)C12—C171.516 (4)
S14—C151.734 (4)C12—C131.346 (4)
F7—C61.357 (4)C13—C201.497 (4)
O10—C91.238 (4)C17—C181.530 (4)
N8—C11.400 (4)C18—C191.505 (5)
N8—C91.377 (4)C19—C201.525 (4)
N16—C151.350 (4)C2—H2A0.9300
N8—H9A0.8600C3—H3A0.9300
N16—H15C0.8600C4—H4A0.9300
N16—H15D0.8600C5—H5A0.9300
C1—C61.388 (4)C17—H22A0.9700
C1—C21.386 (4)C17—H22B0.9700
C2—C31.387 (4)C18—H21A0.9700
C3—C41.382 (6)C18—H21B0.9700
C4—C51.370 (5)C19—H20A0.9700
C5—C61.365 (4)C19—H20B0.9700
C9—C111.449 (4)C20—H18A0.9700
C11—C121.460 (4)C20—H18B0.9700
C11—C151.387 (4)
C13—S14—C1591.95 (12)C12—C17—C18111.9 (2)
C1—N8—C9129.3 (2)C17—C18—C19111.7 (3)
C9—N8—H9A115.00C18—C19—C20112.1 (3)
C1—N8—H9A115.00C13—C20—C19109.8 (2)
H15C—N16—H15D120.00C1—C2—H2A120.00
C15—N16—H15D120.00C3—C2—H2A120.00
C15—N16—H15C120.00C2—C3—H3A119.00
C2—C1—C6117.1 (2)C4—C3—H3A120.00
N8—C1—C2125.8 (2)C3—C4—H4A120.00
N8—C1—C6117.1 (2)C5—C4—H4A120.00
C1—C2—C3119.9 (3)C4—C5—H5A121.00
C2—C3—C4121.0 (3)C6—C5—H5A121.00
C3—C4—C5119.8 (3)C12—C17—H22A109.00
C4—C5—C6118.6 (3)C12—C17—H22B109.00
F7—C6—C5119.4 (2)C18—C17—H22A109.00
C1—C6—C5123.6 (2)C18—C17—H22B109.00
F7—C6—C1117.0 (2)H22A—C17—H22B108.00
N8—C9—C11116.8 (2)C17—C18—H21A109.00
O10—C9—N8120.4 (2)C17—C18—H21B109.00
O10—C9—C11122.8 (2)C19—C18—H21A109.00
C9—C11—C12129.8 (2)C19—C18—H21B109.00
C9—C11—C15118.7 (2)H21A—C18—H21B108.00
C12—C11—C15111.5 (2)C18—C19—H20A109.00
C11—C12—C13113.5 (2)C18—C19—H20B109.00
C13—C12—C17119.3 (2)C20—C19—H20A109.00
C11—C12—C17127.1 (2)C20—C19—H20B109.00
S14—C13—C20120.30 (19)H20A—C19—H20B108.00
C12—C13—C20128.1 (2)C13—C20—H18A110.00
S14—C13—C12111.56 (19)C13—C20—H18B110.00
S14—C15—C11111.52 (19)C19—C20—H18A110.00
N16—C15—C11129.6 (2)C19—C20—H18B110.00
S14—C15—N16118.8 (2)H18A—C20—H18B108.00
C15—S14—C13—C12−0.1 (3)N8—C9—C11—C12−16.9 (5)
C15—S14—C13—C20−178.1 (3)N8—C9—C11—C15161.9 (3)
C13—S14—C15—N16178.9 (3)C9—C11—C12—C13178.4 (3)
C13—S14—C15—C11−0.1 (3)C9—C11—C12—C17−4.5 (6)
C9—N8—C1—C216.1 (5)C15—C11—C12—C13−0.4 (4)
C9—N8—C1—C6−165.1 (3)C15—C11—C12—C17176.8 (3)
C1—N8—C9—O10−7.0 (5)C9—C11—C15—S14−178.6 (2)
C1—N8—C9—C11174.7 (3)C9—C11—C15—N162.4 (5)
N8—C1—C2—C3−178.1 (3)C12—C11—C15—S140.3 (4)
C6—C1—C2—C33.2 (5)C12—C11—C15—N16−178.6 (3)
N8—C1—C6—F7−1.1 (4)C11—C12—C13—S140.3 (4)
N8—C1—C6—C5179.0 (3)C11—C12—C13—C20178.1 (3)
C2—C1—C6—F7177.7 (3)C17—C12—C13—S14−177.1 (3)
C2—C1—C6—C5−2.1 (5)C17—C12—C13—C200.7 (6)
C1—C2—C3—C4−2.8 (6)C11—C12—C17—C18−160.2 (3)
C2—C3—C4—C51.3 (6)C13—C12—C17—C1816.8 (5)
C3—C4—C5—C6−0.2 (6)S14—C13—C20—C19−170.8 (3)
C4—C5—C6—F7−179.2 (3)C12—C13—C20—C1911.5 (5)
C4—C5—C6—C10.6 (6)C12—C17—C18—C19−47.1 (4)
O10—C9—C11—C12164.9 (3)C17—C18—C19—C2061.4 (4)
O10—C9—C11—C15−16.4 (5)C18—C19—C20—C13−41.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H9A···F70.862.262.643 (5)107
N16—H15C···O100.862.162.733 (5)124
N16—H15D···O10i0.862.252.986 (6)143
Symmetry code: (i) x, −y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H9A···F70.862.262.643 (5)107
N16—H15C···O100.862.162.733 (5)124
N16—H15D···O10i0.862.252.986 (6)143
Symmetry code: (i) x, −y, z+1/2.
 

Acknowledgements

The authors thank the University of Mysore and HKBK College of Engineering for support.

References

First citationBonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron, 61, 6580–6589.  Web of Science CrossRef CAS Google Scholar
 First citationBrault, L., Migianu, E., Néguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757–763.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoudhury, A. R., Nagarajan, K. & Guru Row, T. N. (2004). Acta Cryst. C60, o644–o647.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationIsloor, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825–830.  Web of Science CrossRef PubMed CAS 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o807-o808
https://doi.org/10.1107/S2056989015018022
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS