(Z)-4-Chloro-N-{3-[(4-chloro­phen­yl)sulfon­yl]-2,3-di­hydrobenzo[d]thia­zol-2-yl­idene}benzene­sulfonamide

Watkins, S.M.; Hagen, T.J.; Perkins, T.S.; Zheng, C.

doi:10.1107/S2414314617008653

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170865

https://doi.org/10.1107/S2414314617008653

Open

access

(Z)-4-Chloro-N-{3-[(4-chlorophenyl)sulfonyl]-2,3-dihydrobenzo[d]thiazol-2-ylidene}benzenesulfonamide

Sydney M. Watkins,^a Timothy J. Hagen,^a Timothy S. Perkins ^a and Chong Zheng ^a ^*

^aDepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA
^*Correspondence e-mail: czheng@niu.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 April 2017; accepted 9 June 2017; online 20 June 2017)

The title compound, C₁₉H₁₂Cl₂N₂O₄S₃, is related to a ditosylated 2-iminobenzothiazole with the two methyl groups on the two phenyl rings replaced by chlorine. There is a weak intramolecular π–π contact between the two phenyl rings, with a centroid-to-centroid distance of 4.004 (2) Å. The dihedral angle between the rings is 9.96 (13)°. An intramolecular C—H⋯O hydrogen bond stabilizes the molecular conformation.

Keywords: crystal structure; IspF inhibitor; bis-sulfonamide.

CCDC reference: 1555243

Structure description

The methylerythritolphosphate (MEP) pathway is an essential enzymatic pathway for the biosynthesis of isoprenoid precursors present in most bacteria, some protozoa and plants (Persch et al., 2015 ; Frank & Groll, 2017 ; Hunter, 2007 ; Masini & Hirsch, 2014 ; Odom, 2011 ; Hale et al., 2012 ). Inhibition of enzymes from this pathway has tremendous potential to generate new anti-infective agents or herbicides (Frank & Groll, 2017; Witschel et al., 2013 ). The enzyme 2-methylerythritol 2,4-cyclodiphosphate synthase (IspF) is present in the MEP pathway (Zhang et al., 2013 , Geist et al., 2010 , Crane et al., 2006 ). Recently, bis-sulfonamides of ortho-phenylenediamine have been shown to have micromolar inhibitory activity against IspF from Arabidopsis thaliana, Plasmodium falciparum, or Burkholderia pseudomallei (Thelemann et al., 2015 ). In our quest to discover inhibitors of IspF, we synthesized a series of sulfonamide and bis-sulfonamide analogs of 2-aminobenzthiazole that would be capable of binding to the zinc ion of the IspF enzyme. This work resulted in the synthesis of the title compound.

The title compound, shown in Fig. 1, is closely related to a ditosylated 2-iminobenzothiazole (Castanheiro et al., 2017 ) with the two methyl groups on the two phenyl groups replaced by chlorine. However, there are significant structural differences between the structures of the two compounds. The title compound crystallizes in the space group P $[\overline{1}]$ , whereas the methyl compound crystallizes in P2₁/c. Furthermore, the phenyl rings of the title compound lie on one side of the iminobenzothiazole plane, whereas they are on the other side in the methyl compound, as shown in Fig. 2. The torsion angles C31—N32—S2—C24 and C31—N1—S1—C14 in the title compound are −57.91 (16) and −122.8 (2)°, respectively. The corresponding torsion angles of the methyl compound are 60.9 (2) and 107.2 (2)°, respectively. Weak non-classical hydrogen bonds of the type C—H⋯O (Table 1) consolidate the molecular packing in the crystal (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O11ⁱ	0.93	2.53	3.203 (3)	130
C22—H22⋯O22ⁱ	0.93	2.59	3.249 (3)	128
C37—H37⋯O21ⁱⁱ	0.93	2.50	3.339 (3)	151
C34—H34⋯O21	0.93	2.22	2.837 (3)	123
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The molecular conformations of the title compound (left) and the methyl analog (right). The two phenyl groups of the title compound are above the plane of the iminobenzothiazole rings (the plane of the paper), while they are below the plane in the methyl analog.

Figure 3
Packing of the title molecules viewed down the b axis. The white, grey, blue, red, yellow and green spheres are H, C, N, O, S and Cl atoms, respectively.

Synthesis and crystallization

2-Aminobenzothiazole (0.98 mmol) was dissolved in methylene chloride (5 ml) and pyridine (3.8 mmol) in an ice bath. 4-Chlorobenzenesulfonyl chloride (1.0 mmol) was added while stirring, and the reaction was allowed to come to room temperature. The reaction was monitored by TLC, and after 18 h the mixture was concentrated and the remaining solution in pyridine was extracted with water (100 ml) and ethyl acetate (80 ml). The organic layer was washed with brine (30 ml) and dried over anhydrous sodium sulfate. The combined extracts were concentrated to obtain the crude product, which was chromatographed (1: 2 v/v ethyl acetate/hexane) to yield the title compound (0.11 mmol, 11%). The material was recrystallized from a CDCl₃ solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₂Cl₂N₂O₄S₃
M_r	499.39
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	7.1330 (9), 8.1155 (11), 17.798 (2)
α, β, γ (°)	87.747 (2), 81.840 (2), 87.849 (2)
V (Å³)	1018.5 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.66
Crystal size (mm)	0.60 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD PLATFORM
Absorption correction	Multi-scan (SADABS; Bruker, 1999 )
T_min, T_max	0.186, 0.264
No. of measured, independent and observed [I > 2σ(I)] reflections	7549, 3530, 3301
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.04
No. of reflections	3530
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.62
Computer programs: SMART and SAINT (Bruker, 1999), SIR97 (Altomare et al., 1999 ), SHELXL2016 (Sheldrick, 2015 ), XP in SHELXTL (Sheldrick, 2008 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1555243

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008653/wm4046sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup4.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(Z)-4-Chloro-N-{3-[(4-chlorophenyl)sulfonyl]-2,3-dihydrobenzo[d]thiazol-2-ylidene}benzenesulfonamide top

Crystal data top

C₁₉H₁₂Cl₂N₂O₄S₃	Z = 2
M_r = 499.39	F(000) = 508
Triclinic, P1	D_x = 1.628 Mg m⁻³
a = 7.1330 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1155 (11) Å	Cell parameters from 906 reflections
c = 17.798 (2) Å	θ = 2–14°
α = 87.747 (2)°	µ = 0.66 mm⁻¹
β = 81.840 (2)°	T = 293 K
γ = 87.849 (2)°	Fragment, colorless
V = 1018.5 (2) Å³	0.60 × 0.30 × 0.25 mm

Data collection top

Bruker SMART CCD PLATFORM diffractometer	3530 independent reflections
Radiation source: fine-focus sealed tube	3301 reflections with I > 2σ(I)
Detector resolution: 0 pixels mm^-1	R_int = 0.016
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→8
T_min = 0.186, T_max = 0.264	k = −9→9
7549 measured reflections	l = −21→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0448P)² + 0.6375P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.003
3530 reflections	Δρ_max = 0.58 e Å⁻³
271 parameters	Δρ_min = −0.62 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
S1	0.37024 (8)	0.03706 (7)	0.77485 (3)	0.04724 (16)
S2	0.28022 (8)	0.43662 (6)	0.60143 (3)	0.04326 (16)
S3	0.29160 (7)	−0.08482 (6)	0.60835 (3)	0.03773 (15)
Cl1	−0.25853 (15)	0.26317 (14)	1.03311 (5)	0.1060 (4)
Cl2	−0.35272 (13)	0.55565 (14)	0.87265 (5)	0.1002 (3)
N1	0.3383 (3)	0.1643 (2)	0.70469 (10)	0.0446 (4)
C11	−0.0832 (4)	0.2042 (4)	0.95977 (15)	0.0698 (8)
O11	0.5492 (2)	0.0699 (3)	0.79694 (10)	0.0662 (5)
C12	−0.1312 (4)	0.1098 (4)	0.90386 (16)	0.0744 (8)
H12	−0.255949	0.079825	0.904470	0.089*
O12	0.3336 (3)	−0.1291 (2)	0.75832 (9)	0.0611 (5)
C13	0.0077 (4)	0.0596 (4)	0.84652 (15)	0.0634 (7)
H13	−0.022673	−0.004985	0.808228	0.076*
C14	0.1913 (3)	0.1057 (3)	0.84637 (12)	0.0486 (5)
C15	0.2376 (4)	0.2030 (4)	0.90258 (15)	0.0651 (7)
H15	0.361647	0.235004	0.901832	0.078*
C16	0.0982 (5)	0.2520 (4)	0.95971 (16)	0.0771 (8)
H16	0.127549	0.317278	0.997969	0.092*
C21	−0.1739 (4)	0.5178 (3)	0.79780 (14)	0.0581 (6)
O21	0.2169 (3)	0.52024 (18)	0.53771 (9)	0.0608 (5)
C22	−0.2195 (3)	0.4463 (3)	0.73429 (15)	0.0568 (6)
H22	−0.343084	0.416516	0.731865	0.068*
O22	0.4612 (2)	0.4680 (2)	0.62072 (10)	0.0604 (5)
C23	−0.0786 (3)	0.4197 (3)	0.67448 (13)	0.0481 (5)
H23	−0.106709	0.374468	0.630332	0.058*
C24	0.1050 (3)	0.4603 (2)	0.68022 (11)	0.0390 (4)
C25	0.1500 (3)	0.5307 (3)	0.74424 (14)	0.0527 (6)
H25	0.274276	0.557063	0.747588	0.063*
C26	0.0074 (4)	0.5613 (3)	0.80321 (14)	0.0634 (7)
H26	0.033945	0.611211	0.846482	0.076*
C31	0.3056 (3)	0.1145 (2)	0.63973 (11)	0.0364 (4)
N32	0.2750 (2)	0.23124 (19)	0.58320 (9)	0.0380 (4)
C33	0.2499 (3)	0.1635 (2)	0.51252 (11)	0.0341 (4)
C34	0.2275 (3)	0.2439 (3)	0.44425 (12)	0.0421 (5)
H34	0.223853	0.358527	0.439781	0.051*
C35	0.2108 (3)	0.1491 (3)	0.38283 (12)	0.0444 (5)
H35	0.194170	0.201233	0.336651	0.053*
C36	0.2181 (3)	−0.0213 (3)	0.38840 (12)	0.0446 (5)
H36	0.207626	−0.081849	0.346003	0.054*
C37	0.2409 (3)	−0.1021 (3)	0.45611 (12)	0.0408 (4)
H37	0.245905	−0.216761	0.460103	0.049*
C38	0.2561 (3)	−0.0077 (2)	0.51843 (11)	0.0344 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0575 (3)	0.0479 (3)	0.0374 (3)	0.0024 (2)	−0.0118 (2)	−0.0003 (2)
S2	0.0554 (3)	0.0303 (3)	0.0419 (3)	−0.0057 (2)	0.0020 (2)	−0.0013 (2)
S3	0.0444 (3)	0.0310 (3)	0.0382 (3)	−0.00082 (19)	−0.0080 (2)	0.00066 (19)
Cl1	0.1077 (7)	0.1351 (8)	0.0629 (5)	0.0373 (6)	0.0185 (4)	0.0011 (5)
Cl2	0.0861 (6)	0.1271 (8)	0.0752 (5)	0.0237 (5)	0.0257 (4)	−0.0123 (5)
N1	0.0580 (11)	0.0396 (9)	0.0371 (9)	−0.0001 (8)	−0.0102 (8)	−0.0020 (7)
C11	0.0794 (19)	0.0823 (19)	0.0431 (14)	0.0196 (15)	0.0004 (13)	0.0029 (13)
O11	0.0552 (10)	0.0930 (14)	0.0529 (10)	0.0019 (9)	−0.0177 (8)	−0.0013 (9)
C12	0.0550 (15)	0.106 (2)	0.0613 (17)	0.0027 (15)	−0.0084 (13)	0.0035 (16)
O12	0.0945 (13)	0.0420 (9)	0.0471 (9)	0.0052 (8)	−0.0141 (9)	0.0016 (7)
C13	0.0618 (16)	0.0836 (19)	0.0475 (13)	−0.0034 (13)	−0.0154 (12)	−0.0072 (12)
C14	0.0582 (13)	0.0509 (13)	0.0373 (11)	−0.0007 (10)	−0.0100 (10)	0.0009 (9)
C15	0.0734 (17)	0.0726 (17)	0.0507 (14)	−0.0130 (14)	−0.0076 (12)	−0.0140 (12)
C16	0.097 (2)	0.084 (2)	0.0501 (15)	−0.0054 (17)	−0.0037 (15)	−0.0209 (14)
C21	0.0602 (15)	0.0570 (14)	0.0524 (14)	0.0115 (11)	0.0045 (11)	−0.0013 (11)
O21	0.1006 (14)	0.0339 (8)	0.0444 (9)	0.0050 (8)	−0.0013 (8)	0.0044 (7)
C22	0.0466 (13)	0.0589 (14)	0.0638 (15)	0.0001 (11)	−0.0053 (11)	0.0003 (12)
O22	0.0537 (10)	0.0565 (10)	0.0687 (11)	−0.0206 (8)	0.0060 (8)	−0.0099 (8)
C23	0.0537 (13)	0.0443 (12)	0.0478 (12)	−0.0029 (10)	−0.0115 (10)	−0.0051 (9)
C24	0.0473 (11)	0.0286 (9)	0.0405 (11)	−0.0001 (8)	−0.0041 (9)	−0.0028 (8)
C25	0.0536 (13)	0.0529 (13)	0.0537 (13)	−0.0041 (10)	−0.0096 (10)	−0.0158 (11)
C26	0.0749 (18)	0.0683 (16)	0.0480 (14)	0.0060 (13)	−0.0088 (12)	−0.0228 (12)
C31	0.0372 (10)	0.0342 (10)	0.0371 (10)	0.0003 (8)	−0.0032 (8)	0.0004 (8)
N32	0.0482 (9)	0.0302 (8)	0.0349 (8)	0.0010 (7)	−0.0039 (7)	−0.0014 (6)
C33	0.0310 (9)	0.0351 (10)	0.0352 (10)	0.0003 (7)	−0.0014 (7)	−0.0028 (8)
C34	0.0455 (11)	0.0394 (11)	0.0405 (11)	0.0004 (9)	−0.0046 (9)	0.0032 (9)
C35	0.0461 (11)	0.0517 (12)	0.0360 (11)	−0.0025 (9)	−0.0092 (9)	0.0039 (9)
C36	0.0457 (11)	0.0500 (12)	0.0393 (11)	−0.0057 (9)	−0.0077 (9)	−0.0063 (9)
C37	0.0420 (11)	0.0370 (10)	0.0441 (11)	−0.0045 (8)	−0.0067 (9)	−0.0049 (9)
C38	0.0303 (9)	0.0357 (10)	0.0367 (10)	−0.0017 (7)	−0.0033 (7)	0.0008 (8)

Geometric parameters (Å, º) top

S1—O11	1.4252 (18)	C21—C26	1.370 (4)
S1—O12	1.4331 (18)	C21—C22	1.375 (4)
S1—N1	1.6244 (18)	C22—C23	1.374 (3)
S1—C14	1.761 (2)	C22—H22	0.9300
S2—O22	1.4165 (18)	C23—C24	1.381 (3)
S2—O21	1.4186 (17)	C23—H23	0.9300
S2—N32	1.7133 (16)	C24—C25	1.377 (3)
S2—C24	1.752 (2)	C25—C26	1.377 (3)
S3—C31	1.743 (2)	C25—H25	0.9300
S3—C38	1.7439 (19)	C26—H26	0.9300
Cl1—C11	1.743 (3)	C31—N32	1.389 (3)
Cl2—C21	1.737 (2)	N32—C33	1.429 (2)
N1—C31	1.294 (3)	C33—C34	1.383 (3)
C11—C16	1.365 (4)	C33—C38	1.389 (3)
C11—C12	1.368 (4)	C34—C35	1.383 (3)
C12—C13	1.380 (4)	C34—H34	0.9300
C12—H12	0.9300	C35—C36	1.382 (3)
C13—C14	1.375 (3)	C35—H35	0.9300
C13—H13	0.9300	C36—C37	1.376 (3)
C14—C15	1.381 (3)	C36—H36	0.9300
C15—C16	1.377 (4)	C37—C38	1.391 (3)
C15—H15	0.9300	C37—H37	0.9300
C16—H16	0.9300

O11—S1—O12	118.29 (12)	C21—C22—H22	120.7
O11—S1—N1	107.50 (11)	C22—C23—C24	119.7 (2)
O12—S1—N1	111.51 (9)	C22—C23—H23	120.2
O11—S1—C14	108.24 (11)	C24—C23—H23	120.2
O12—S1—C14	108.49 (11)	C25—C24—C23	121.4 (2)
N1—S1—C14	101.45 (10)	C25—C24—S2	119.38 (17)
O22—S2—O21	119.94 (11)	C23—C24—S2	119.02 (16)
O22—S2—N32	108.05 (10)	C26—C25—C24	118.7 (2)
O21—S2—N32	104.94 (9)	C26—C25—H25	120.7
O22—S2—C24	110.58 (10)	C24—C25—H25	120.7
O21—S2—C24	108.54 (10)	C21—C26—C25	119.7 (2)
N32—S2—C24	103.39 (9)	C21—C26—H26	120.2
C31—S3—C38	90.95 (9)	C25—C26—H26	120.2
C31—N1—S1	122.39 (15)	N1—C31—N32	118.90 (18)
C16—C11—C12	121.6 (3)	N1—C31—S3	130.18 (16)
C16—C11—Cl1	119.4 (2)	N32—C31—S3	110.92 (14)
C12—C11—Cl1	118.9 (3)	C31—N32—C33	114.44 (16)
C11—C12—C13	119.2 (3)	C31—N32—S2	119.26 (13)
C11—C12—H12	120.4	C33—N32—S2	126.24 (13)
C13—C12—H12	120.4	C34—C33—C38	120.44 (18)
C14—C13—C12	119.6 (3)	C34—C33—N32	129.24 (18)
C14—C13—H13	120.2	C38—C33—N32	110.29 (16)
C12—C13—H13	120.2	C35—C34—C33	118.10 (19)
C13—C14—C15	120.7 (2)	C35—C34—H34	120.9
C13—C14—S1	119.75 (18)	C33—C34—H34	120.9
C15—C14—S1	119.6 (2)	C36—C35—C34	121.6 (2)
C16—C15—C14	119.4 (3)	C36—C35—H35	119.2
C16—C15—H15	120.3	C34—C35—H35	119.2
C14—C15—H15	120.3	C37—C36—C35	120.63 (19)
C11—C16—C15	119.5 (3)	C37—C36—H36	119.7
C11—C16—H16	120.2	C35—C36—H36	119.7
C15—C16—H16	120.2	C36—C37—C38	118.20 (19)
C26—C21—C22	121.9 (2)	C36—C37—H37	120.9
C26—C21—Cl2	119.4 (2)	C38—C37—H37	120.9
C22—C21—Cl2	118.7 (2)	C33—C38—C37	121.04 (18)
C23—C22—C21	118.6 (2)	C33—C38—S3	113.31 (14)
C23—C22—H22	120.7	C37—C38—S3	125.62 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O11ⁱ	0.93	2.53	3.203 (3)	130
C22—H22···O22ⁱ	0.93	2.59	3.249 (3)	128
C37—H37···O21ⁱⁱ	0.93	2.50	3.339 (3)	151
C34—H34···O21	0.93	2.22	2.837 (3)	123

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z.

Funding information

Funding for this research was provided by: NIH (award No. 1R15AI113653-01 to TJH).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1999). SMART and SAINT. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Castanheiro, T., Suffert, J., Donnard, M. & Gulea, M. (2017). Phosphorus Sulfur Silicon, 192, 162–165. CSD CrossRef CAS Google Scholar
Crane, C. M., Kaiser, J., Ramsden, N. L., Lauw, S., Rohdich, F., Eisenreich, W., Hunter, W. N., Bacher, A. & Diederich, F. (2006). Angew. Chem. Int. Ed. 45, 1069–1074. CrossRef CAS Google Scholar
Frank, A. & Groll, M. (2017). Chem. Rev. 117, 5675–5703. CrossRef CAS PubMed Google Scholar
Geist, J. G., Lauw, S., Illarionova, V., Illarionov, B., Fischer, M., Gräwert, T., Rohdich, F., Eisenreich, W., Kaiser, J., Groll, M., Scheurer, C., Wittlin, S., Alonso-Gómez, J. L., Schweizer, W. B., Bacher, A. & Diederich, F. (2010). ChemMedChem, 5, 1092–1101. CSD CrossRef CAS PubMed Google Scholar
Hale, I., O'Neill, P. M., Berry, N. G., Odom, A. & Sharma, R. (2012). MedChemComm, 3, 418–433. CrossRef CAS Google Scholar
Hunter, W. N. (2007). J. Biol. Chem. 282, 21573–21577. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Masini, T. & Hirsch, A. K. H. (2014). J. Med. Chem. 57, 9740–9763. CrossRef CAS PubMed Google Scholar
Odom, A. R. (2011). PLoS Pathog. 7, e1002323. CrossRef PubMed Google Scholar
Persch, E., Dumele, O. & Diederich, F. (2015). Angew. Chem. Int. Ed. 54, 3290–3327. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Thelemann, J., Illarionov, B., Barylyuk, K., Geist, J., Kirchmair, J., Schneider, P., Anthore, L., Root, K., Trapp, N., Bacher, A., Witschel, M., Zenobi, R., Fischer, M., Schneider, G. & Diederich, F. (2015). ChemMedChem, 10, 2090–2098. CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Witschel, M., Röhl, F., Niggeweg, R. & Newton, T. (2013). Pest. Manag. Sci. 69, 559–563. CrossRef CAS PubMed Google Scholar
Zhang, Z., Jakkaraju, S., Blain, J., Gogol, K., Zhao, L., Hartley, R. C., Karlsson, C. A., Staker, B. L., Edwards, T. E., Stewart, L. J., Myler, P. J., Clare, M., Begley, D. W., Horn, J. R. & Hagen, T. J. (2013). Bioorg. Med. Chem. Lett. 23, 6860–6863. CrossRef CAS PubMed 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.