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

Journal logoIUCrDATA
ISSN: 2414-3146

1-Benzyl-2-benzyl­sulfanyl-4,4-di­phenyl-4,5-di­hydro-1H-imidazol-5-one

CROSSMARK_Color_square_no_text.svg

aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: rakrad@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 January 2017; accepted 8 January 2017; online 13 January 2017)

The asymmetric unit of the title compound, C29H24N2OS, consists of two independent mol­ecules having markedly different orientations of the substit­uents on the central imidazole ring. Apart from a weak C—H⋯S hydrogen bond, the inter­molecular inter­actions in the crystal are all of the C—H⋯π(ring) type and form a three-dimensional network. One of the phenyl rings is disordered over two sets of sites in 0.713 (9): 0.287 (9) ratio.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Hydantoin derivatives are known for their physiological activity as anti­convulsants (Weichet, 1974[Weichet, B. L. (1974). J. Czech. Patent, 151, 744-747.]) and are also widely used in many other pharmacological applications such as anti­arrhythmic (Havera et al., 1976[Havera, H. J. & Strycker, W. G. (1976). US Patent 3 904 909.]), anti­diabetic (Rizzi et al., 1989[Rizzi, J. P., Schnur, R. C., Hutson, N. J., Kraus, K. G. & Kelbaugh, P. R. (1989). J. Med. Chem. 32, 1208-1213.]), fungicidal (Thenmozhiyal et al., 2004[Thenmozhiyal, J. C., Wong, P. T. H. & Chui, W.-K. (2004). J. Med. Chem. 47, 1527-1535.]), anti-carcinogen (Lamothe et al., 2002[Lamothe, M., Lannuzel, M. & Perez, M. (2002). J. Comb. Chem. 4, 73-78.]), anti­viral (el-Barbary et al., 1994[el-Barbary, A. A., Khodair, A. I., Pedersen, E. B. & Nielsen, C. (1994). J. Med. Chem. 37, 73-77.]) and anti-HIV (Khodair et al., 1997[Khodair, A. I., el-Subbagh, H. I. & el-Emam, A. A. (1997). Boll. Chim. Farm. 136, 561-567.]) agents.

The asymmetric unit of the title compound contains two independent mol­ecules (A and B; Fig. 1[link]). No part of one mol­ecule is directly superimposable on the other, as shown by the AutoMolFit plot (Fig. 2[link]), and the dihedral angles between the central five-membered imidazole rings and the peripheral benzene rings; see Table 1[link]. The phenyl ring attached to atom C4 is rotationally disordered by 20.3 (2)° about the C4⋯C5A(or C5B) bond.

Table 1
Dihedral angles (°)

Ring 1 Ring 2 Dihedral angle
N1/N2/C1–C3 C5A–C10A 80.83 (16)
N1/N2/C1–C3 C12–C17 76.92 (11)
N1/N2/C1–C3 C18–C23 66.59 (11)
N1/N2/C1–C3 C24–C29 58.40 (11)
     
N3/N4/C30–C32 C34–C39 70.43 (12)
N3/N4/C30–C32 C41–C46 75.48 (10)
N3/N4/C30–C32 C47–C52 69.00 (10)
N3/N4/C30–C32 C53–C58 72.92 (11)
[Figure 1]
Figure 1
The mol­ecular structure of the two independent mol­ecules (mol­ecule A left, mol­ecule B right) of the title compound, with the atom labelling and 25% probability displacement ellipsoids. Only the major component (C5A–C10A) of the disordered phenyl ring is shown.
[Figure 2]
Figure 2
The AutoMolFit (PLATON; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) of mol­ecule B (red) on mol­ecule A (black); only the major component (C5A–C10A) of the disordered phenyl ring is shown.

In the crystal, the two mol­ecules are linked by a C—H⋯S hydrogen bond (Table 2[link]). There are a number of C—H⋯π(ring) inter­actions present (Fig. 3[link] and Table 2[link]), linking the mol­ecules to form a three-dimensional network.

Table 2
Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg5, Cg8 and Cg9 are the centroids of the C5A–C10A, C12–C17, C24–C29, C41–C46 and C47–C52 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11A⋯S2i 0.97 2.95 3.591 (2) 125
C4—H4BCg8ii 0.97 2.97 3.693 (2) 133
C11—H11BCg9i 0.97 2.83 3.524 (2) 129
C22—H22⋯Cg8iii 0.93 2.77 3.554 (3) 143
C35—H35⋯Cg5 0.93 2.77 3.697 (3) 172
C40—H40ACg3ii 0.97 2.81 3.556 (2) 134
C55—H55⋯Cg2iv 0.93 2.84 3.725 (3) 160
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z+1.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound. The C—H⋯S hydrogen bonds and C—H⋯π(ring) inter­actions are shown as, respectively, black and orange dotted lines (see Table 2[link]; only the major component (C5A–C10A) of the disordered phenyl ring is shown).

Synthesis and crystallization

To a solution of 5,5-diphenyl-2-thioxoimidazolidin-4-one (1.86 mol, 500.00 mg) in 10 ml DMF were added benzyl­chloride (3.73 mol), K2CO3 (3.73 mol) and a catalytic amount of tetra­butyl­ammonium bromide. The mixture was stirred at room temperature for 24 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol solution to afford colourless block-like crystals of the title compound (yield 60%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The phenyl ring attached to atom C4 of mol­ecule A (Fig. 1[link]) is disordered by a 20.3 (2)° rotation about the C4⋯C5A(or C5B) axis. The two components were refined as rigid hexa­gons with the displacement parameters of corresponding carbon atoms restrained to be comparable. The refined occupancy ratio (A:B) is = 0.713 (9): 0.287 (9).

Table 3
Experimental details

Crystal data
Chemical formula C29H24N2OS
Mr 448.56
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 298
a, b, c (Å) 8.7383 (6), 14.1443 (9), 19.2405 (13)
α, β, γ (°) 90.732 (1), 92.181 (1), 91.394 (1)
V3) 2375.4 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.16
Crystal size (mm) 0.26 × 0.17 × 0.14
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.80, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections 22757, 11555, 6260
Rint 0.034
(sin θ/λ)max−1) 0.675
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.158, 1.00
No. of reflections 11555
No. of parameters 590
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.42, −0.17
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-Benzyl-2-benzylsulfanyl-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one top
Crystal data top
C29H24N2OSZ = 4
Mr = 448.56F(000) = 944
Triclinic, P1Dx = 1.254 Mg m3
a = 8.7383 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.1443 (9) ÅCell parameters from 4999 reflections
c = 19.2405 (13) Åθ = 2.5–24.0°
α = 90.732 (1)°µ = 0.16 mm1
β = 92.181 (1)°T = 298 K
γ = 91.394 (1)°Block, colourless
V = 2375.4 (3) Å30.26 × 0.17 × 0.14 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
11555 independent reflections
Radiation source: fine-focus sealed tube6260 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8.3333 pixels mm-1θmax = 28.7°, θmin = 1.1°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1919
Tmin = 0.80, Tmax = 0.98l = 2525
22757 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0667P)2]
where P = (Fo2 + 2Fc2)/3
11555 reflections(Δ/σ)max = 0.001
590 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 30 sec/frame was used.

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.

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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.93 - 0.97 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. The phenyl ring attached to C4 is disordered by a 20.3 (2)° rotation about the C4···C5A(or B) axis. The two components of the disorder were refined as rigid hexagons with the displacement parameters of corresponding carbon atoms restrained to be comparable.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.10005 (6)0.34338 (4)0.19831 (3)0.05694 (16)
O10.07564 (18)0.42328 (11)0.43322 (8)0.0769 (5)
N10.14932 (18)0.27553 (11)0.32783 (8)0.0502 (4)
N20.00086 (18)0.40342 (10)0.32105 (8)0.0519 (4)
C10.0883 (2)0.33659 (13)0.28826 (10)0.0477 (4)
C20.1037 (2)0.29822 (13)0.39949 (10)0.0507 (5)
C30.0032 (2)0.38249 (14)0.39060 (11)0.0557 (5)
C40.2168 (2)0.24238 (14)0.18086 (11)0.0629 (6)
H4A0.25290.24720.13400.075*
H4B0.30590.24510.21250.075*
C5A0.1368 (4)0.1480 (2)0.1879 (2)0.0505 (6)0.713 (9)
C6A0.2058 (4)0.0894 (3)0.2367 (2)0.0606 (10)0.713 (9)
H6A0.29250.11060.26240.073*0.713 (9)
C7A0.1451 (6)0.0008 (3)0.24713 (16)0.0715 (12)0.713 (9)
H7A0.19120.04000.27980.086*0.713 (9)
C8A0.0155 (4)0.0325 (2)0.2087 (3)0.0828 (12)0.713 (9)
H8A0.02510.09290.21570.099*0.713 (9)
C9A0.0534 (3)0.0261 (2)0.1599 (3)0.0817 (14)0.713 (9)
H9A0.14010.00490.13420.098*0.713 (9)
C10A0.0072 (5)0.1163 (2)0.1495 (2)0.0663 (11)0.713 (9)
H10A0.03890.15550.11690.080*0.713 (9)
C5B0.1503 (11)0.1425 (7)0.1908 (6)0.0505 (6)0.287 (9)
C6B0.1623 (14)0.0806 (9)0.2461 (5)0.0606 (10)0.287 (9)
H6B0.22340.09690.28520.073*0.287 (9)
C7B0.0829 (14)0.0058 (8)0.2429 (5)0.0715 (12)0.287 (9)
H7B0.09090.04730.27990.086*0.287 (9)
C8B0.0084 (12)0.0303 (6)0.1844 (6)0.0828 (12)0.287 (9)
H8B0.06150.08810.18230.099*0.287 (9)
C9B0.0204 (13)0.0317 (7)0.1291 (6)0.0817 (14)0.287 (9)
H9B0.08150.01530.08990.098*0.287 (9)
C10B0.0590 (13)0.1181 (7)0.1323 (5)0.0663 (11)0.287 (9)
H10B0.05100.15960.09520.080*0.287 (9)
C110.0818 (2)0.48205 (13)0.28914 (12)0.0595 (5)
H11A0.16500.49940.31830.071*
H11B0.12630.46120.24440.071*
C120.0194 (2)0.56819 (13)0.27865 (11)0.0536 (5)
C130.1074 (3)0.60719 (14)0.33321 (12)0.0635 (6)
H130.10540.57950.37680.076*
C140.1979 (3)0.68627 (16)0.32411 (14)0.0749 (7)
H140.25760.71100.36140.090*
C150.2014 (3)0.72913 (17)0.26111 (16)0.0795 (7)
H150.26250.78310.25540.095*
C160.1147 (3)0.69218 (18)0.20651 (15)0.0813 (7)
H160.11640.72110.16340.098*
C170.0234 (3)0.61138 (16)0.21486 (12)0.0678 (6)
H170.03510.58640.17730.081*
C180.0139 (2)0.21601 (13)0.43057 (10)0.0529 (5)
C190.0179 (3)0.21582 (17)0.50014 (12)0.0714 (6)
H190.01700.26600.52860.086*
C200.1009 (3)0.14228 (19)0.52832 (14)0.0830 (7)
H200.12130.14310.57540.100*
C210.1530 (3)0.06838 (18)0.48679 (15)0.0819 (7)
H210.20830.01850.50560.098*
C220.1239 (3)0.06809 (17)0.41832 (14)0.0825 (7)
H220.15970.01770.39020.099*
C230.0416 (3)0.14148 (15)0.38929 (12)0.0674 (6)
H230.02370.14050.34200.081*
C240.2489 (2)0.32512 (14)0.44394 (10)0.0545 (5)
C250.2496 (3)0.39422 (15)0.49521 (11)0.0665 (6)
H250.16050.42640.50380.080*
C260.3823 (4)0.41545 (19)0.53367 (13)0.0899 (9)
H260.38170.46180.56840.108*
C270.5133 (4)0.3704 (2)0.52195 (15)0.0953 (10)
H270.60230.38640.54790.114*
C280.5149 (3)0.3002 (2)0.47116 (15)0.0915 (9)
H280.60450.26840.46320.110*
C290.3822 (3)0.27788 (18)0.43224 (12)0.0707 (6)
H290.38280.23080.39810.085*
S20.37902 (6)0.34701 (4)0.71215 (3)0.05625 (16)
O20.60094 (16)0.40572 (10)0.95067 (7)0.0659 (4)
N30.35844 (18)0.26232 (10)0.83655 (7)0.0478 (4)
N40.50878 (17)0.39542 (10)0.83677 (8)0.0486 (4)
C300.4122 (2)0.32950 (12)0.80067 (9)0.0456 (4)
C310.4139 (2)0.28060 (12)0.90933 (9)0.0478 (4)
C320.5216 (2)0.36797 (13)0.90528 (10)0.0499 (5)
C330.2558 (2)0.24505 (14)0.69060 (10)0.0568 (5)
H33A0.19260.23150.72980.068*
H33B0.18820.26040.65140.068*
C340.3414 (2)0.15830 (14)0.67276 (10)0.0532 (5)
C350.4014 (3)0.15061 (17)0.60760 (13)0.0771 (7)
H350.38520.19820.57540.093*
C360.4842 (3)0.0741 (2)0.58992 (17)0.1015 (10)
H360.52520.07030.54610.122*
C370.5071 (4)0.0035 (2)0.6358 (2)0.1095 (11)
H370.56380.04850.62340.131*
C380.4469 (4)0.0087 (2)0.70049 (18)0.1054 (10)
H380.46140.04020.73180.126*
C390.3639 (3)0.08743 (16)0.71928 (13)0.0722 (6)
H390.32400.09160.76330.087*
C400.5916 (2)0.47636 (13)0.80867 (11)0.0571 (5)
H40A0.63530.45740.76520.068*
H40B0.67560.49460.84090.068*
C410.4928 (2)0.56105 (13)0.79590 (10)0.0497 (5)
C420.4154 (2)0.60108 (14)0.84996 (11)0.0577 (5)
H420.42230.57490.89400.069*
C430.3283 (2)0.67962 (16)0.83860 (12)0.0667 (6)
H430.27630.70580.87520.080*
C440.3170 (3)0.71991 (16)0.77418 (14)0.0707 (6)
H440.25790.77290.76690.085*
C450.3940 (3)0.68097 (17)0.72096 (13)0.0714 (6)
H450.38780.70800.67720.086*
C460.4814 (2)0.60162 (15)0.73131 (11)0.0610 (5)
H460.53270.57560.69440.073*
C470.2719 (2)0.30247 (13)0.95070 (9)0.0490 (5)
C480.1514 (3)0.23789 (17)0.94676 (11)0.0712 (6)
H480.16090.18080.92300.085*
C490.0147 (3)0.2586 (2)0.97858 (13)0.0858 (8)
H490.06750.21560.97520.103*
C500.0016 (3)0.3416 (2)1.01452 (13)0.0837 (8)
H500.08990.35551.03510.100*
C510.1231 (3)0.40426 (18)1.02018 (12)0.0739 (7)
H510.11460.46011.04560.089*
C520.2580 (2)0.38532 (14)0.98854 (10)0.0579 (5)
H520.34000.42840.99270.070*
C530.5052 (2)0.19834 (13)0.93806 (10)0.0502 (5)
C540.5734 (2)0.13524 (15)0.89392 (11)0.0652 (6)
H540.55940.14130.84600.078*
C550.6617 (3)0.06354 (17)0.92016 (14)0.0786 (7)
H550.70610.02140.88990.094*
C560.6842 (3)0.05415 (17)0.99051 (14)0.0779 (7)
H560.74380.00581.00820.093*
C570.6184 (3)0.11649 (18)1.03456 (13)0.0774 (7)
H570.63400.11051.08240.093*
C580.5293 (3)0.18795 (15)1.00898 (11)0.0664 (6)
H580.48490.22961.03960.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0650 (3)0.0517 (3)0.0544 (3)0.0022 (3)0.0049 (2)0.0039 (2)
O10.0881 (11)0.0683 (10)0.0761 (10)0.0265 (9)0.0185 (9)0.0159 (8)
N10.0554 (10)0.0458 (9)0.0500 (9)0.0096 (8)0.0050 (8)0.0027 (7)
N20.0538 (10)0.0411 (9)0.0612 (10)0.0098 (7)0.0028 (8)0.0018 (8)
C10.0465 (11)0.0415 (10)0.0548 (11)0.0012 (9)0.0018 (9)0.0032 (9)
C20.0570 (12)0.0447 (11)0.0507 (11)0.0085 (9)0.0043 (9)0.0059 (9)
C30.0560 (12)0.0462 (11)0.0650 (14)0.0067 (10)0.0048 (10)0.0091 (10)
C40.0613 (13)0.0626 (13)0.0656 (13)0.0007 (11)0.0164 (11)0.0072 (11)
C5A0.0517 (13)0.0496 (12)0.0506 (12)0.0127 (11)0.0016 (10)0.0045 (10)
C6A0.070 (3)0.0546 (17)0.0581 (17)0.0146 (19)0.0051 (19)0.0030 (14)
C7A0.076 (4)0.0615 (18)0.0778 (19)0.019 (2)0.003 (2)0.0074 (14)
C8A0.088 (2)0.0642 (17)0.096 (4)0.0002 (16)0.004 (3)0.016 (2)
C9A0.078 (2)0.0668 (18)0.098 (4)0.0157 (18)0.017 (2)0.018 (3)
C10A0.060 (3)0.0620 (15)0.076 (3)0.0030 (19)0.006 (2)0.0127 (16)
C5B0.0517 (13)0.0496 (12)0.0506 (12)0.0127 (11)0.0016 (10)0.0045 (10)
C6B0.070 (3)0.0546 (17)0.0581 (17)0.0146 (19)0.0051 (19)0.0030 (14)
C7B0.076 (4)0.0615 (18)0.0778 (19)0.019 (2)0.003 (2)0.0074 (14)
C8B0.088 (2)0.0642 (17)0.096 (4)0.0002 (16)0.004 (3)0.016 (2)
C9B0.078 (2)0.0668 (18)0.098 (4)0.0157 (18)0.017 (2)0.018 (3)
C10B0.060 (3)0.0620 (15)0.076 (3)0.0030 (19)0.006 (2)0.0127 (16)
C110.0531 (12)0.0452 (11)0.0798 (15)0.0125 (10)0.0102 (10)0.0023 (10)
C120.0528 (12)0.0447 (11)0.0640 (13)0.0167 (9)0.0000 (10)0.0003 (10)
C130.0717 (14)0.0507 (12)0.0677 (14)0.0040 (11)0.0039 (11)0.0015 (10)
C140.0740 (16)0.0568 (14)0.0931 (18)0.0006 (12)0.0050 (13)0.0073 (13)
C150.0740 (17)0.0512 (13)0.114 (2)0.0073 (12)0.0099 (16)0.0089 (14)
C160.0870 (18)0.0704 (16)0.0893 (18)0.0236 (15)0.0164 (15)0.0293 (14)
C170.0700 (15)0.0652 (14)0.0686 (14)0.0194 (12)0.0045 (12)0.0049 (12)
C180.0548 (12)0.0468 (11)0.0578 (12)0.0078 (10)0.0058 (10)0.0002 (9)
C190.0827 (16)0.0674 (14)0.0642 (14)0.0096 (13)0.0153 (12)0.0070 (11)
C200.0876 (18)0.0861 (18)0.0766 (16)0.0065 (15)0.0232 (14)0.0066 (14)
C210.0756 (17)0.0683 (16)0.103 (2)0.0088 (13)0.0200 (15)0.0084 (15)
C220.0854 (18)0.0687 (16)0.0922 (19)0.0209 (14)0.0050 (15)0.0119 (14)
C230.0690 (14)0.0654 (14)0.0672 (14)0.0074 (12)0.0024 (11)0.0058 (11)
C240.0595 (13)0.0520 (12)0.0520 (12)0.0041 (10)0.0020 (10)0.0061 (9)
C250.0859 (16)0.0556 (13)0.0569 (13)0.0109 (12)0.0046 (12)0.0010 (10)
C260.124 (2)0.0737 (17)0.0683 (16)0.0311 (18)0.0228 (17)0.0164 (13)
C270.096 (2)0.107 (2)0.0788 (19)0.0389 (19)0.0321 (17)0.0371 (17)
C280.0670 (16)0.127 (2)0.0813 (18)0.0023 (17)0.0053 (14)0.0386 (18)
C290.0640 (14)0.0871 (17)0.0616 (14)0.0094 (13)0.0022 (11)0.0114 (12)
S20.0694 (4)0.0486 (3)0.0510 (3)0.0041 (2)0.0011 (2)0.0068 (2)
O20.0669 (9)0.0606 (9)0.0683 (9)0.0139 (8)0.0090 (8)0.0109 (7)
N30.0575 (10)0.0421 (8)0.0437 (9)0.0031 (7)0.0015 (7)0.0006 (7)
N40.0506 (9)0.0396 (8)0.0555 (10)0.0020 (7)0.0026 (7)0.0009 (7)
C300.0482 (11)0.0396 (10)0.0493 (11)0.0039 (9)0.0047 (8)0.0011 (8)
C310.0532 (11)0.0431 (10)0.0467 (11)0.0039 (9)0.0013 (9)0.0010 (8)
C320.0509 (11)0.0444 (11)0.0542 (12)0.0005 (9)0.0040 (9)0.0051 (9)
C330.0541 (12)0.0597 (13)0.0560 (12)0.0061 (10)0.0063 (9)0.0027 (10)
C340.0469 (11)0.0542 (12)0.0582 (12)0.0035 (9)0.0028 (9)0.0078 (10)
C350.0855 (17)0.0692 (15)0.0772 (16)0.0111 (14)0.0238 (13)0.0150 (13)
C360.088 (2)0.106 (2)0.111 (2)0.0009 (18)0.0309 (18)0.041 (2)
C370.100 (2)0.091 (2)0.137 (3)0.0375 (19)0.008 (2)0.041 (2)
C380.122 (2)0.0768 (19)0.116 (3)0.0307 (18)0.033 (2)0.0021 (18)
C390.0792 (16)0.0636 (14)0.0731 (15)0.0079 (13)0.0114 (12)0.0008 (12)
C400.0497 (11)0.0466 (11)0.0755 (14)0.0034 (9)0.0115 (10)0.0038 (10)
C410.0471 (11)0.0415 (10)0.0603 (12)0.0075 (9)0.0056 (9)0.0034 (9)
C420.0607 (13)0.0537 (12)0.0591 (12)0.0002 (10)0.0069 (10)0.0002 (10)
C430.0623 (14)0.0598 (13)0.0786 (16)0.0023 (11)0.0108 (12)0.0074 (12)
C440.0609 (14)0.0539 (13)0.0977 (18)0.0027 (11)0.0035 (13)0.0098 (13)
C450.0710 (15)0.0697 (15)0.0737 (15)0.0044 (13)0.0007 (12)0.0254 (13)
C460.0613 (13)0.0589 (13)0.0636 (13)0.0052 (11)0.0143 (10)0.0038 (11)
C470.0534 (11)0.0494 (11)0.0440 (11)0.0016 (9)0.0018 (9)0.0052 (9)
C480.0727 (15)0.0759 (16)0.0646 (14)0.0149 (13)0.0096 (12)0.0028 (12)
C490.0671 (16)0.120 (2)0.0697 (16)0.0258 (16)0.0086 (13)0.0112 (16)
C500.0663 (16)0.124 (2)0.0627 (15)0.0194 (17)0.0150 (12)0.0208 (16)
C510.0794 (17)0.0801 (17)0.0639 (15)0.0206 (14)0.0109 (13)0.0046 (12)
C520.0618 (13)0.0552 (12)0.0572 (12)0.0073 (10)0.0034 (10)0.0026 (10)
C530.0537 (12)0.0440 (10)0.0525 (12)0.0030 (9)0.0009 (9)0.0012 (9)
C540.0740 (15)0.0627 (14)0.0595 (13)0.0089 (12)0.0050 (11)0.0009 (11)
C550.0828 (17)0.0650 (15)0.0891 (19)0.0245 (13)0.0041 (14)0.0049 (13)
C560.0765 (16)0.0628 (15)0.0938 (19)0.0127 (13)0.0131 (14)0.0096 (14)
C570.0881 (17)0.0768 (16)0.0665 (15)0.0100 (14)0.0151 (13)0.0134 (13)
C580.0787 (15)0.0629 (14)0.0571 (13)0.0083 (12)0.0055 (11)0.0019 (11)
Geometric parameters (Å, º) top
S1—C11.7414 (19)C26—H260.9300
S1—C41.811 (2)C27—C281.385 (4)
O1—C31.205 (2)C27—H270.9300
N1—C11.272 (2)C28—C291.384 (3)
N1—C21.483 (2)C28—H280.9300
N2—C31.375 (2)C29—H290.9300
N2—C11.399 (2)S2—C301.7386 (19)
N2—C111.462 (2)S2—C331.813 (2)
C2—C181.528 (3)O2—C321.205 (2)
C2—C31.539 (3)N3—C301.273 (2)
C2—C241.540 (3)N3—C311.482 (2)
C4—C5A1.502 (3)N4—C321.380 (2)
C4—C5B1.531 (8)N4—C301.402 (2)
C4—H4A0.9700N4—C401.460 (2)
C4—H4B0.9700C31—C531.524 (3)
C5A—C6A1.3900C31—C471.535 (3)
C5A—C10A1.3900C31—C321.540 (3)
C6A—C7A1.3900C33—C341.495 (3)
C6A—H6A0.9300C33—H33A0.9700
C7A—C8A1.3900C33—H33B0.9700
C7A—H7A0.9300C34—C391.365 (3)
C8A—C9A1.3900C34—C351.381 (3)
C8A—H8A0.9300C35—C361.363 (4)
C9A—C10A1.3900C35—H350.9300
C9A—H9A0.9300C36—C371.355 (4)
C10A—H10A0.9300C36—H360.9300
C5B—C6B1.3900C37—C381.371 (4)
C5B—C10B1.3900C37—H370.9300
C6B—C7B1.3900C38—C391.395 (4)
C6B—H6B0.9300C38—H380.9300
C7B—C8B1.3900C39—H390.9300
C7B—H7B0.9300C40—C411.511 (3)
C8B—C9B1.3900C40—H40A0.9700
C8B—H8B0.9300C40—H40B0.9700
C9B—C10B1.3900C41—C461.377 (3)
C9B—H9B0.9300C41—C421.385 (3)
C10B—H10B0.9300C42—C431.377 (3)
C11—C121.508 (3)C42—H420.9300
C11—H11A0.9700C43—C441.372 (3)
C11—H11B0.9700C43—H430.9300
C12—C131.379 (3)C44—C451.364 (3)
C12—C171.379 (3)C44—H440.9300
C13—C141.371 (3)C45—C461.385 (3)
C13—H130.9300C45—H450.9300
C14—C151.363 (3)C46—H460.9300
C14—H140.9300C47—C481.376 (3)
C15—C161.363 (3)C47—C521.382 (3)
C15—H150.9300C48—C491.398 (3)
C16—C171.392 (3)C48—H480.9300
C16—H160.9300C49—C501.365 (4)
C17—H170.9300C49—H490.9300
C18—C191.377 (3)C50—C511.366 (4)
C18—C231.379 (3)C50—H500.9300
C19—C201.382 (3)C51—C521.378 (3)
C19—H190.9300C51—H510.9300
C20—C211.366 (3)C52—H520.9300
C20—H200.9300C53—C581.383 (3)
C21—C221.351 (3)C53—C541.385 (3)
C21—H210.9300C54—C551.379 (3)
C22—C231.384 (3)C54—H540.9300
C22—H220.9300C55—C561.369 (3)
C23—H230.9300C55—H550.9300
C24—C251.379 (3)C56—C571.367 (3)
C24—C291.381 (3)C56—H560.9300
C25—C261.377 (3)C57—C581.376 (3)
C25—H250.9300C57—H570.9300
C26—C271.348 (4)C58—H580.9300
C1—S1—C4100.73 (10)C26—C27—C28119.8 (3)
C1—N1—C2106.73 (15)C26—C27—H27120.1
C3—N2—C1108.21 (15)C28—C27—H27120.1
C3—N2—C11124.11 (16)C29—C28—C27119.6 (3)
C1—N2—C11127.67 (17)C29—C28—H28120.2
N1—C1—N2115.74 (17)C27—C28—H28120.2
N1—C1—S1126.99 (15)C24—C29—C28120.3 (2)
N2—C1—S1117.24 (14)C24—C29—H29119.9
N1—C2—C18111.41 (15)C28—C29—H29119.9
N1—C2—C3104.30 (15)C30—S2—C33100.11 (9)
C18—C2—C3108.69 (15)C30—N3—C31106.47 (15)
N1—C2—C24108.53 (15)C32—N4—C30107.94 (15)
C18—C2—C24111.90 (15)C32—N4—C40124.05 (16)
C3—C2—C24111.78 (15)C30—N4—C40127.90 (16)
O1—C3—N2125.46 (19)N3—C30—N4116.01 (16)
O1—C3—C2129.7 (2)N3—C30—S2126.77 (14)
N2—C3—C2104.85 (16)N4—C30—S2117.22 (13)
C5A—C4—S1114.8 (2)N3—C31—C53111.69 (14)
C5B—C4—S1119.4 (4)N3—C31—C47106.37 (15)
C5A—C4—H4A108.6C53—C31—C47113.66 (15)
S1—C4—H4A108.6N3—C31—C32104.60 (14)
C5A—C4—H4B108.6C53—C31—C32108.77 (15)
S1—C4—H4B108.6C47—C31—C32111.38 (15)
H4A—C4—H4B107.5O2—C32—N4126.24 (18)
C6A—C5A—C10A120.0O2—C32—C31129.04 (18)
C6A—C5A—C4114.3 (3)N4—C32—C31104.72 (15)
C10A—C5A—C4125.7 (3)C34—C33—S2113.61 (14)
C7A—C6A—C5A120.0C34—C33—H33A108.8
C7A—C6A—H6A120.0S2—C33—H33A108.8
C5A—C6A—H6A120.0C34—C33—H33B108.8
C6A—C7A—C8A120.0S2—C33—H33B108.8
C6A—C7A—H7A120.0H33A—C33—H33B107.7
C8A—C7A—H7A120.0C39—C34—C35119.2 (2)
C9A—C8A—C7A120.0C39—C34—C33121.96 (19)
C9A—C8A—H8A120.0C35—C34—C33118.8 (2)
C7A—C8A—H8A120.0C36—C35—C34120.8 (3)
C8A—C9A—C10A120.0C36—C35—H35119.6
C8A—C9A—H9A120.0C34—C35—H35119.6
C10A—C9A—H9A120.0C37—C36—C35120.4 (3)
C9A—C10A—C5A120.0C37—C36—H36119.8
C9A—C10A—H10A120.0C35—C36—H36119.8
C5A—C10A—H10A120.0C36—C37—C38120.1 (3)
C6B—C5B—C10B120.0C36—C37—H37120.0
C6B—C5B—C4131.7 (7)C38—C37—H37120.0
C10B—C5B—C4108.2 (7)C37—C38—C39119.9 (3)
C5B—C6B—C7B120.0C37—C38—H38120.1
C5B—C6B—H6B120.0C39—C38—H38120.1
C7B—C6B—H6B120.0C34—C39—C38119.7 (2)
C6B—C7B—C8B120.0C34—C39—H39120.1
C6B—C7B—H7B120.0C38—C39—H39120.1
C8B—C7B—H7B120.0N4—C40—C41113.60 (15)
C9B—C8B—C7B120.0N4—C40—H40A108.8
C9B—C8B—H8B120.0C41—C40—H40A108.8
C7B—C8B—H8B120.0N4—C40—H40B108.8
C8B—C9B—C10B120.0C41—C40—H40B108.8
C8B—C9B—H9B120.0H40A—C40—H40B107.7
C10B—C9B—H9B120.0C46—C41—C42118.73 (19)
C9B—C10B—C5B120.0C46—C41—C40121.05 (18)
C9B—C10B—H10B120.0C42—C41—C40120.19 (18)
C5B—C10B—H10B120.0C43—C42—C41120.1 (2)
N2—C11—C12113.47 (15)C43—C42—H42119.9
N2—C11—H11A108.9C41—C42—H42119.9
C12—C11—H11A108.9C44—C43—C42121.1 (2)
N2—C11—H11B108.9C44—C43—H43119.5
C12—C11—H11B108.9C42—C43—H43119.5
H11A—C11—H11B107.7C45—C44—C43118.9 (2)
C13—C12—C17118.3 (2)C45—C44—H44120.5
C13—C12—C11120.70 (19)C43—C44—H44120.5
C17—C12—C11120.98 (19)C44—C45—C46120.8 (2)
C14—C13—C12120.9 (2)C44—C45—H45119.6
C14—C13—H13119.6C46—C45—H45119.6
C12—C13—H13119.6C41—C46—C45120.3 (2)
C15—C14—C13120.8 (2)C41—C46—H46119.8
C15—C14—H14119.6C45—C46—H46119.8
C13—C14—H14119.6C48—C47—C52119.34 (19)
C16—C15—C14119.3 (2)C48—C47—C31117.69 (18)
C16—C15—H15120.3C52—C47—C31122.90 (18)
C14—C15—H15120.3C47—C48—C49119.7 (2)
C15—C16—C17120.4 (2)C47—C48—H48120.2
C15—C16—H16119.8C49—C48—H48120.2
C17—C16—H16119.8C50—C49—C48120.3 (2)
C12—C17—C16120.2 (2)C50—C49—H49119.9
C12—C17—H17119.9C48—C49—H49119.9
C16—C17—H17119.9C49—C50—C51119.9 (2)
C19—C18—C23118.23 (19)C49—C50—H50120.1
C19—C18—C2120.87 (18)C51—C50—H50120.1
C23—C18—C2120.86 (18)C50—C51—C52120.5 (2)
C18—C19—C20121.1 (2)C50—C51—H51119.7
C18—C19—H19119.4C52—C51—H51119.7
C20—C19—H19119.4C51—C52—C47120.2 (2)
C21—C20—C19119.8 (2)C51—C52—H52119.9
C21—C20—H20120.1C47—C52—H52119.9
C19—C20—H20120.1C58—C53—C54118.22 (19)
C22—C21—C20119.7 (2)C58—C53—C31120.74 (17)
C22—C21—H21120.1C54—C53—C31120.94 (17)
C20—C21—H21120.1C55—C54—C53120.7 (2)
C21—C22—C23121.1 (2)C55—C54—H54119.6
C21—C22—H22119.4C53—C54—H54119.6
C23—C22—H22119.4C56—C55—C54120.3 (2)
C18—C23—C22120.0 (2)C56—C55—H55119.8
C18—C23—H23120.0C54—C55—H55119.8
C22—C23—H23120.0C57—C56—C55119.4 (2)
C25—C24—C29119.2 (2)C57—C56—H56120.3
C25—C24—C2122.1 (2)C55—C56—H56120.3
C29—C24—C2118.72 (19)C56—C57—C58120.8 (2)
C26—C25—C24119.9 (3)C56—C57—H57119.6
C26—C25—H25120.1C58—C57—H57119.6
C24—C25—H25120.1C57—C58—C53120.5 (2)
C27—C26—C25121.3 (3)C57—C58—H58119.7
C27—C26—H26119.4C53—C58—H58119.7
C25—C26—H26119.4
C2—N1—C1—N20.7 (2)C25—C26—C27—C281.1 (4)
C2—N1—C1—S1178.81 (14)C26—C27—C28—C290.8 (4)
C3—N2—C1—N12.0 (2)C25—C24—C29—C280.5 (3)
C11—N2—C1—N1178.89 (17)C2—C24—C29—C28179.9 (2)
C3—N2—C1—S1176.27 (13)C27—C28—C29—C240.0 (4)
C11—N2—C1—S12.8 (2)C31—N3—C30—N42.8 (2)
C4—S1—C1—N10.5 (2)C31—N3—C30—S2177.60 (14)
C4—S1—C1—N2177.61 (14)C32—N4—C30—N30.5 (2)
C1—N1—C2—C18119.89 (17)C40—N4—C30—N3176.89 (16)
C1—N1—C2—C32.81 (19)C32—N4—C30—S2179.09 (13)
C1—N1—C2—C24116.48 (17)C40—N4—C30—S22.7 (2)
C1—N2—C3—O1176.15 (19)C33—S2—C30—N30.84 (19)
C11—N2—C3—O13.0 (3)C33—S2—C30—N4178.71 (13)
C1—N2—C3—C23.60 (19)C30—N3—C31—C53122.17 (16)
C11—N2—C3—C2177.29 (16)C30—N3—C31—C47113.29 (17)
N1—C2—C3—O1175.8 (2)C30—N3—C31—C324.69 (19)
C18—C2—C3—O156.9 (3)C30—N4—C32—O2176.50 (18)
C24—C2—C3—O167.1 (3)C40—N4—C32—O20.0 (3)
N1—C2—C3—N23.92 (19)C30—N4—C32—C313.46 (19)
C18—C2—C3—N2122.86 (17)C40—N4—C32—C31179.99 (15)
C24—C2—C3—N2113.14 (17)N3—C31—C32—O2175.02 (19)
C1—S1—C4—C5A72.3 (2)C53—C31—C32—O255.6 (3)
C1—S1—C4—C5B68.6 (5)C47—C31—C32—O270.5 (3)
S1—C4—C5A—C6A121.1 (2)N3—C31—C32—N44.94 (19)
S1—C4—C5A—C10A60.5 (4)C53—C31—C32—N4124.40 (16)
C10A—C5A—C6A—C7A0.0C47—C31—C32—N4109.57 (17)
C4—C5A—C6A—C7A178.5 (3)C30—S2—C33—C3487.24 (16)
C5A—C6A—C7A—C8A0.0S2—C33—C34—C39101.1 (2)
C6A—C7A—C8A—C9A0.0S2—C33—C34—C3577.9 (2)
C7A—C8A—C9A—C10A0.0C39—C34—C35—C361.0 (3)
C8A—C9A—C10A—C5A0.0C33—C34—C35—C36178.0 (2)
C6A—C5A—C10A—C9A0.0C34—C35—C36—C370.9 (4)
C4—C5A—C10A—C9A178.3 (4)C35—C36—C37—C380.0 (5)
S1—C4—C5B—C6B96.4 (7)C36—C37—C38—C390.9 (5)
S1—C4—C5B—C10B80.7 (7)C35—C34—C39—C380.1 (3)
C10B—C5B—C6B—C7B0.0C33—C34—C39—C38178.9 (2)
C4—C5B—C6B—C7B176.8 (10)C37—C38—C39—C340.9 (4)
C5B—C6B—C7B—C8B0.0C32—N4—C40—C41104.9 (2)
C6B—C7B—C8B—C9B0.0C30—N4—C40—C4179.3 (2)
C7B—C8B—C9B—C10B0.0N4—C40—C41—C46124.3 (2)
C8B—C9B—C10B—C5B0.0N4—C40—C41—C4257.7 (2)
C6B—C5B—C10B—C9B0.0C46—C41—C42—C430.4 (3)
C4—C5B—C10B—C9B177.5 (8)C40—C41—C42—C43178.47 (18)
C3—N2—C11—C1299.0 (2)C41—C42—C43—C440.4 (3)
C1—N2—C11—C1282.1 (2)C42—C43—C44—C450.1 (3)
N2—C11—C12—C1352.8 (3)C43—C44—C45—C460.5 (3)
N2—C11—C12—C17128.9 (2)C42—C41—C46—C450.0 (3)
C17—C12—C13—C140.7 (3)C40—C41—C46—C45178.05 (18)
C11—C12—C13—C14179.06 (19)C44—C45—C46—C410.5 (3)
C12—C13—C14—C150.9 (3)N3—C31—C47—C4853.6 (2)
C13—C14—C15—C160.5 (4)C53—C31—C47—C4869.7 (2)
C14—C15—C16—C170.1 (4)C32—C31—C47—C48167.01 (17)
C13—C12—C17—C160.1 (3)N3—C31—C47—C52123.34 (18)
C11—C12—C17—C16178.43 (19)C53—C31—C47—C52113.3 (2)
C15—C16—C17—C120.3 (3)C32—C31—C47—C529.9 (2)
N1—C2—C18—C19169.36 (18)C52—C47—C48—C492.6 (3)
C3—C2—C18—C1976.3 (2)C31—C47—C48—C49174.44 (19)
C24—C2—C18—C1947.7 (2)C47—C48—C49—C501.2 (4)
N1—C2—C18—C2312.6 (3)C48—C49—C50—C510.8 (4)
C3—C2—C18—C23101.7 (2)C49—C50—C51—C521.5 (4)
C24—C2—C18—C23134.4 (2)C50—C51—C52—C470.1 (3)
C23—C18—C19—C201.1 (3)C48—C47—C52—C512.0 (3)
C2—C18—C19—C20179.1 (2)C31—C47—C52—C51174.91 (18)
C18—C19—C20—C210.2 (4)N3—C31—C53—C58161.27 (18)
C19—C20—C21—C220.5 (4)C47—C31—C53—C5840.9 (2)
C20—C21—C22—C230.1 (4)C32—C31—C53—C5883.8 (2)
C19—C18—C23—C221.4 (3)N3—C31—C53—C5422.4 (2)
C2—C18—C23—C22179.4 (2)C47—C31—C53—C54142.79 (18)
C21—C22—C23—C180.8 (4)C32—C31—C53—C5492.5 (2)
N1—C2—C24—C25143.97 (18)C58—C53—C54—C550.6 (3)
C18—C2—C24—C2592.7 (2)C31—C53—C54—C55177.0 (2)
C3—C2—C24—C2529.5 (3)C53—C54—C55—C560.5 (4)
N1—C2—C24—C2936.5 (2)C54—C55—C56—C570.0 (4)
C18—C2—C24—C2986.8 (2)C55—C56—C57—C580.4 (4)
C3—C2—C24—C29150.99 (19)C56—C57—C58—C530.3 (4)
C29—C24—C25—C260.3 (3)C54—C53—C58—C570.2 (3)
C2—C24—C25—C26179.80 (19)C31—C53—C58—C57176.6 (2)
C24—C25—C26—C270.5 (4)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg5, Cg8 and Cg9 are the centroids of the C5A–C10A, C12–C17, C24–C29, C41–C46 and C47–C52 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11A···S2i0.972.953.591 (2)125
C4—H4B···Cg8ii0.972.973.693 (2)133
C11—H11B···Cg9i0.972.833.524 (2)129
C22—H22···Cg8iii0.932.773.554 (3)143
C35—H35···Cg50.932.773.697 (3)172
C40—H40A···Cg3ii0.972.813.556 (2)134
C55—H55···Cg2iv0.932.843.725 (3)160
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x+1, y, z+1.
Dihedral angles (°) top
Ring 1Ring 2Dihedral angle
N1/N2/C1–C3C5A–C10A80.83 (16)
N1/N2/C1–C3C12–C1776.92 (11)
N1/N2/C1–C3C18–C2366.59 (11)
N1/N2/C1–C3C24–C2958.40 (11)
N3/N4/C30–C32C34–C3970.43 (12)
N3/N4/C30–C32C41–C4675.48 (10)
N3/N4/C30–C32C47–C5269.00 (10)
N3/N4/C30–C32C53–C5872.92 (11)
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

First citationel-Barbary, A. A., Khodair, A. I., Pedersen, E. B. & Nielsen, C. (1994). J. Med. Chem. 37, 73–77.  CAS Google Scholar
First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHavera, H. J. & Strycker, W. G. (1976). US Patent 3 904 909.  Google Scholar
First citationKhodair, A. I., el-Subbagh, H. I. & el-Emam, A. A. (1997). Boll. Chim. Farm. 136, 561–567.  CAS Google Scholar
First citationLamothe, M., Lannuzel, M. & Perez, M. (2002). J. Comb. Chem. 4, 73–78.  Web of Science CrossRef CAS Google Scholar
First citationRizzi, J. P., Schnur, R. C., Hutson, N. J., Kraus, K. G. & Kelbaugh, P. R. (1989). J. Med. Chem. 32, 1208–1213.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationThenmozhiyal, J. C., Wong, P. T. H. & Chui, W.-K. (2004). J. Med. Chem. 47, 1527–1535.  Web of Science CrossRef CAS Google Scholar
First citationWeichet, B. L. (1974). J. Czech. Patent, 151, 744–747.  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 logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds