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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2016 June 1; 72(Pt 6): 797–800.
Published online 2016 May 10. doi:  10.1107/S2056989016007611
PMCID: PMC4908551

Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosyl­acryl­amide and (E)-3-phenyl-2-(m-tol­yl)-N-tosyl­acryl­amide

Abstract

In the title N-tosyl­acryl­amide compounds, C20H17NO4S, (I), and C23H21NO3S, (II), the conformation about the C=C bond is E. The acryl­amide groups, [–NH—C(=O)—C=C–], are almost planar, with the N—C—C=C torsion angle being −170.18 (14)° in (I) and −168.01 (17)° in (II). In (I), the furan, phenyl and 4-methyl­benzene rings are inclined to the acryl­amide mean plane by 26.47 (11), 69.01 (8) and 82.49 (9)°, respectively. In (II), the phenyl, 3-methyl­benzene and 4-methyl­benzene rings are inclined to the acryl­amide mean plane by 11.61 (10), 78.44 (10) and 78.24 (10)°, respectively. There is an intra­molecular C—H(...)π inter­action present in compound (II). In the crystals of both compounds, mol­ecules are linked by pairs of N—H(...)O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. In (I), the dimers are reinforced by C—H(...)O hydrogen bonds and linked by C—H(...)π inter­actions, forming chains along [011]. In the crystal of (II), the dimers are linked via C—H(...)O hydrogen bonds, forming chains along [100]. The chains are further linked by C—H(...)π inter­actions, forming layers parallel to (010).

Keywords: crystal structure, Cu-catalysed azide-alkyne cyclo­addition reaction, CuAAC, N—H(...)O hydrogen bonding, inversion dimers, C—H(...)π inter­actions

Chemical context  

The Cu-catalysed azide-alkyne cyclo­addition (CuAAC) reaction constitutes one of the most inter­esting examples of the click reaction (Bae et al., 2005  ; Cheng et al., 2012  ; Mondal & Pan, 2015  ). Trisubstituted alkenes are commonly found in the mol­ecular skeleton of natural products and bioactive substances, and they are important building blocks in organic chemistry (Zhu et al., 2012  ; Manikandan & Jeganmohan, 2015  ). Therefore, it is highly desirable to develop new efficient and general methods for the stereoselective synthesis of tris­ubstituted alkenes (Ram & Tittal, 2014  ; Bae et al., 2005  ). As part of our work on the application of the CuAAC reaction (Cheng et al., 2012  ), we report herein on the synthesis and crystal structures of the title compounds, (I) and (II).

Structural commentary  

The mol­ecular structures of the title compounds, (I) and (II), are illustrated in Figs. 1  and 2  , respectively. Both mol­ecules adopt an E conformation about the C=C bonds; C9=C16 in (I) and C9=C10 in (II). The acryl­amide groups, [–NH—C(=O)—C=C–], are almost planar with the N1—C8—C9=C16 torsion angle being −170.18 (14) ° in (I), and the N1—C8—C9=C10 torsion angle being −168.01 (17)° in (II). The mol­ecular conformation of the two mol­ecules differ somewhat, as shown by the structure overlap illustrated in Fig. 3  .

An external file that holds a picture, illustration, etc.
Object name is e-72-00797-scheme1.jpg

Figure 1
The mol­ecular structure of compound (I), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.
Figure 2
The mol­ecular structure of compound (II), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The intra­molecular C—H(...)π inter­action is shown by the blue dashed arrow ...
Figure 3
A view of the overlap of mol­ecules (I) (blue) and (II) (red).

In (I) the furan, phenyl and 4-methyl­benzene rings are inclined to the acryl­amide mean plane [N1/O3/C8/C9/C16; maximum deviation of 0.0779 (15) Å for atom C9] by 26.47 (11), 69.01 (8) and 82.49 (9)°, respectively. The 4-methyl­benzene ring is inclined to the furan and phenyl rings by 72.25 (11) and 19.00 (9)°, respectively, the latter two rings being inclined to one another by 66.28 (11)°. In (II), the phenyl, 3-methyl­benzene and 4-methyl­benzene rings are inclined to the acryl­amide mean plane [N1/O3/C8/C9/C10; maximum deviation of 0.0998 (18) Å for atom C9] by 11.61 (10), 78.44 (10) and 78.24 (10)°, respectively. The 4-methyl­benzene ring is inclined to the phenyl and 3-methyl­benzene rings by dihedral angles of 78.33 (11) and 13.10 (11)°, respectively, the latter two rings being inclined to one another by 75.86 (11)°. There is an intra­molecular C—H(...)π inter­action present in compound (II) involving the adjacent phenyl and 3-methyl­benzene rings (Table 2 and Fig. 2  ).

Supra­molecular features  

In the crystal of both compounds, mol­ecules are linked by pairs of N—H(...)O hydrogen bonds (Tables 1  and 2  ), forming inversion dimers with An external file that holds a picture, illustration, etc.
Object name is e-72-00797-efi1.jpg(8) ring motifs, as shown in Fig. 4  for (I) and Fig. 5  for (II). In (I), the dimers are reinforced by C—H(...)O hydrogen bonds and linked by C—H(...)π inter­actions (Table 1  ), forming chains propagating along [011]. In the crystal of (II), the dimers are linked via C—H(...)O hydrogen bonds, forming chains propagating along [100]. There is also a C—H(...)π inter­action present, linking the chains to form layers lying parallel to (010).

Figure 4
The crystal packing of compound (I), viewed along the b-axis direction. The hydrogen bonds are shown as dashed lines (see Table 1  ), and for clarity only the H atoms involved in the various inter­actions have been included.
Figure 5
The crystal packing of compound (II), viewed along the b-axis direction. The hydrogen bonds are shown as dashed lines (see Table 2  ), and for clarity only the H atoms involved in the various inter­actions have been included.
Table 1
Hydrogen-bond geometry (Å, °) for (I)
Table 2
Hydrogen-bond geometry (Å, °) for (II)

Database survey  

A search of the Cambridge Structural Database (Version 5.37, update February 2016; Groom et al., 2016  ) for the substructure N-(phenyl­sulfon­yl)acryl­amide yielded five hits. Four of these compounds involve the 4-methyl­benzene­sulfonyl group and one compound involves a phenyl­sulfonyl group. This later compound, 2-(4-chloro­phen­yl)-3-(2-fur­yl)-N-(phenyl­sulfon­yl)acryl­amide (BIZGOI; Yu & Cao, 2014  ), is very similar to compound (I). The principal difference in the conformation of this mol­ecule with respect to that of compound (I) is the dihedral angle involving the pyran ring and the adjacent aromatic ring, a phenyl ring in (I) and a chloro­benzene ring in BIZGOI; this angle is 66.18 (11)° in (I) but 88.84 (13)° in BIZGOI. In the crystal of BIZGOI, mol­ecules are linked by pairs of N—H(...)O hydrogen bonds, forming inversion dimers with an An external file that holds a picture, illustration, etc.
Object name is e-72-00797-efi1.jpg(8) ring motif, similar to the arrangement in the crystals of compounds (I) and (II).

Synthesis and crystallization  

Compound (I): 4-methyl­benzene­sulfonyl azide (4.5 mmol), CuI (5.7 mg, 0.03 mmol), Et4NI (7.7 mg, 0.03 mmol), ethynyl­benzene (4.5 mmol), and furan-2-carbaldehyde (3 mmol) were suspended in CH2Cl2 (5 ml) in a 10 mL Schlenk tube under nitro­gen at rt. LiOH (8.64 mg, 3.6mmol) was then added, and the resulting solution was stirred at this temperature. Upon full consumption of furan-2-carbaldehyde, the reaction was quenched by saturated aqueous NH4Cl (5 ml) and extracted with CH2Cl2 (10 ml × 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chroma­tography on silica gel (n-hexa­ne/EtOAc 5:1 v/v) to afford compound (I) as a white solid (yield: 0.79 g, 72%). Part of the purified product was redissolved in n-hexa­ne/EtOAc and after slow evaporation over several days, colourless crystals suitable for analysis by X-ray diffraction were formed.

Compound (II): 4-methyl­benzene­sulfonyl azide (4.5 mmol), CuI (5.7 mg, 0.03 mmol), Et4NI (7.7 mg, 0.03 mmol), 1-eth­yn­yl-3-methyl­benzene (4.5 mmol), and benzaldehyde (3 mmol) were suspended in CH2Cl2 (5 ml) in a 10 mL Schlenk tube under nitro­gen at rt. LiOH (8.64 mg, 3.6mmol) was then added, and the resulting solution was stirred at this temperature. Upon full consumption of benzaldehyde, the reaction was quenched by saturated aqueous NH4Cl (5 ml) and extracted with CH2Cl2 (3 × 10 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chroma­tography on silica gel (n-hexa­ne/EtOAc 5:1 v/v) to afford compound (II) as a white solid (0.82, 70%). Part of the purified product was redissolved in n-hexa­ne/EtOAc and after slow evaporation over several days, colourless block-like crystals were obtained.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3  . H atoms were placed in geom­etrically idealized positions and constrained to ride on their parent atoms: C—H = 0.93–0.96 Å and N—H = 0.86 Å, with U iso(H) = 1.5U eq(C-meth­yl) and 1.2U eq(C,N) for other H atoms.

Table 3
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989016007611/su5296sup1.cif

CCDC references: 1478730, 1478729

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the support of the Natural Science Foundation of Anhui Higher Education Institution (No. KJ2013B166), and the Chaohu College Foundation for Doctors in China, Project of Undergraduate Innovative Training (No. 201410380018).

supplementary crystallographic information

Crystal data

C23H21NO3SZ = 2
Mr = 391.47F(000) = 412
Triclinic, P1Dx = 1.325 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2595 (10) ÅCell parameters from 5782 reflections
b = 10.1158 (11) Åθ = 2.4–27.5°
c = 11.9271 (12) ŵ = 0.19 mm1
α = 72.396 (1)°T = 293 K
β = 67.518 (1)°Block, colorless
γ = 79.346 (1)°0.23 × 0.22 × 0.19 mm
V = 980.89 (18) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3422 independent reflections
Radiation source: fine-focus sealed tube3082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 18.4 pixels mm-1θmax = 25.0°, θmin = 1.9°
phi and ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2008)k = −11→12
Tmin = 0.958, Tmax = 0.965l = −13→14
7136 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0455P)2 + 0.4517P] where P = (Fo2 + 2Fc2)/3
3422 reflections(Δ/σ)max = 0.020
255 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

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 esds 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 > 2sigma(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)

xyzUiso*/Ueq
S10.95790 (5)0.26449 (4)0.05551 (4)0.0436 (1)
O11.04900 (15)0.37065 (13)−0.04088 (12)0.0547 (4)
O20.90276 (16)0.16492 (14)0.02290 (13)0.0569 (5)
O30.68817 (16)0.16464 (13)0.28061 (14)0.0597 (5)
N10.80466 (16)0.35319 (15)0.13653 (14)0.0451 (5)
C11.3053 (3)−0.0307 (3)0.4111 (2)0.0727 (9)
C21.2199 (2)0.0429 (2)0.32171 (19)0.0528 (6)
C31.1116 (3)−0.0221 (2)0.3086 (3)0.0722 (8)
C41.0318 (3)0.0434 (2)0.2278 (2)0.0675 (8)
C51.05970 (19)0.17789 (17)0.15828 (17)0.0428 (5)
C61.1700 (3)0.2442 (2)0.1675 (2)0.0633 (8)
C71.2484 (3)0.1761 (2)0.2490 (2)0.0693 (8)
C80.68331 (19)0.28973 (18)0.24058 (16)0.0428 (5)
C90.55006 (18)0.38643 (17)0.29569 (16)0.0386 (5)
C100.44805 (19)0.32908 (18)0.40848 (16)0.0426 (5)
C110.3048 (2)0.39036 (19)0.48921 (16)0.0429 (5)
C120.1949 (2)0.2998 (2)0.57903 (18)0.0562 (7)
C130.0586 (3)0.3480 (3)0.6607 (2)0.0681 (8)
C140.0297 (2)0.4866 (3)0.6551 (2)0.0658 (8)
C150.1372 (3)0.5781 (2)0.5689 (2)0.0640 (7)
C160.2740 (2)0.5309 (2)0.48597 (18)0.0543 (6)
C170.52982 (18)0.53233 (17)0.22211 (15)0.0394 (5)
C180.60582 (19)0.63895 (17)0.22063 (16)0.0419 (5)
C190.5787 (2)0.77626 (19)0.15814 (18)0.0526 (6)
C200.4696 (3)0.8034 (2)0.0996 (2)0.0756 (8)
C210.3957 (3)0.6992 (3)0.0975 (3)0.0837 (10)
C220.4264 (2)0.5634 (2)0.1573 (2)0.0606 (7)
C230.6632 (3)0.8906 (2)0.1559 (2)0.0737 (8)
H10.800200.442600.113000.0540*
H1A1.23480−0.037800.495800.1090*
H1B1.391500.020900.394900.1090*
H1C1.34430−0.122200.399600.1090*
H31.09170−0.112900.355800.0870*
H40.95940−0.003000.220200.0810*
H61.191500.334300.119000.0760*
H71.322800.221500.255000.0830*
H100.472000.235200.440700.0510*
H120.213800.205000.584000.0670*
H13−0.013700.286000.719600.0820*
H14−0.062800.519200.709700.0790*
H150.118000.672300.566300.0770*
H160.345700.593700.427600.0650*
H180.676900.618200.262500.0500*
H200.445700.894800.060400.0910*
H210.324500.720200.055700.1000*
H220.377800.492600.154200.0730*
H23A0.744800.915800.075700.1100*
H23B0.708300.859000.220600.1100*
H23C0.590600.970000.169800.1100*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0405 (2)0.0405 (2)0.0452 (3)−0.0018 (2)−0.0106 (2)−0.0112 (2)
O10.0506 (7)0.0506 (7)0.0466 (7)−0.0047 (6)−0.0035 (6)−0.0068 (6)
O20.0592 (8)0.0539 (8)0.0666 (9)−0.0005 (6)−0.0276 (7)−0.0231 (7)
O30.0540 (8)0.0372 (7)0.0687 (9)−0.0055 (6)−0.0057 (7)−0.0057 (6)
N10.0395 (8)0.0350 (7)0.0501 (9)−0.0023 (6)−0.0074 (6)−0.0071 (6)
C10.0784 (15)0.0720 (15)0.0750 (15)0.0034 (12)−0.0401 (13)−0.0171 (12)
C20.0521 (11)0.0516 (11)0.0550 (11)0.0029 (8)−0.0188 (9)−0.0178 (9)
C30.0748 (14)0.0441 (11)0.0995 (18)−0.0114 (10)−0.0474 (14)0.0052 (11)
C40.0659 (13)0.0444 (11)0.0996 (17)−0.0145 (9)−0.0470 (13)0.0009 (11)
C50.0381 (9)0.0391 (9)0.0479 (10)−0.0021 (7)−0.0104 (7)−0.0132 (7)
C60.0806 (15)0.0465 (11)0.0705 (14)−0.0199 (10)−0.0357 (12)−0.0049 (10)
C70.0858 (16)0.0602 (13)0.0792 (15)−0.0231 (11)−0.0462 (13)−0.0091 (11)
C80.0392 (9)0.0405 (9)0.0462 (10)−0.0066 (7)−0.0135 (7)−0.0072 (8)
C90.0353 (8)0.0389 (9)0.0424 (9)−0.0058 (7)−0.0150 (7)−0.0080 (7)
C100.0421 (9)0.0403 (9)0.0451 (10)−0.0073 (7)−0.0159 (8)−0.0072 (7)
C110.0410 (9)0.0501 (10)0.0359 (9)−0.0088 (7)−0.0120 (7)−0.0075 (7)
C120.0557 (11)0.0594 (12)0.0504 (11)−0.0194 (9)−0.0073 (9)−0.0154 (9)
C130.0538 (12)0.0868 (16)0.0556 (12)−0.0284 (11)0.0036 (10)−0.0227 (11)
C140.0470 (11)0.0891 (17)0.0547 (12)−0.0032 (11)−0.0042 (9)−0.0280 (12)
C150.0663 (13)0.0598 (12)0.0554 (12)0.0057 (10)−0.0132 (10)−0.0167 (10)
C160.0537 (11)0.0515 (11)0.0453 (10)−0.0060 (9)−0.0068 (9)−0.0074 (8)
C170.0324 (8)0.0425 (9)0.0369 (8)−0.0024 (7)−0.0082 (7)−0.0067 (7)
C180.0389 (9)0.0418 (9)0.0403 (9)−0.0023 (7)−0.0119 (7)−0.0067 (7)
C190.0506 (10)0.0417 (10)0.0511 (11)−0.0034 (8)−0.0076 (9)−0.0048 (8)
C200.0734 (15)0.0528 (13)0.0834 (16)−0.0018 (11)−0.0364 (13)0.0165 (11)
C210.0796 (16)0.0807 (17)0.0924 (18)−0.0071 (13)−0.0594 (15)0.0143 (14)
C220.0561 (12)0.0641 (13)0.0659 (13)−0.0120 (10)−0.0339 (10)−0.0019 (10)
C230.0822 (16)0.0438 (11)0.0838 (16)−0.0112 (10)−0.0195 (13)−0.0091 (11)

Geometric parameters (Å, º)

S1—O21.4161 (16)C18—C191.391 (3)
S1—O11.4258 (14)C19—C201.380 (3)
S1—N11.6605 (16)C19—C231.500 (3)
S1—C51.7571 (19)C20—C211.370 (4)
O3—C81.209 (2)C21—C221.377 (4)
N1—C81.390 (2)C1—H1A0.9600
C1—C21.504 (3)C1—H1B0.9600
N1—H10.8600C1—H1C0.9600
C2—C31.374 (4)C3—H30.9300
C2—C71.374 (3)C4—H40.9300
C3—C41.375 (4)C6—H60.9300
C4—C51.374 (3)C7—H70.9300
C5—C61.374 (3)C10—H100.9300
C6—C71.377 (4)C12—H120.9300
C8—C91.495 (3)C13—H130.9300
C9—C101.341 (2)C14—H140.9300
C9—C171.491 (2)C15—H150.9300
C10—C111.467 (3)C16—H160.9300
C11—C161.389 (3)C18—H180.9300
C11—C121.393 (3)C20—H200.9300
C12—C131.378 (3)C21—H210.9300
C13—C141.364 (4)C22—H220.9300
C14—C151.374 (3)C23—H23A0.9600
C15—C161.384 (3)C23—H23B0.9600
C17—C221.386 (3)C23—H23C0.9600
C17—C181.385 (3)
O2—S1—O1119.71 (8)C20—C21—C22120.2 (3)
O2—S1—N1108.68 (9)C17—C22—C21119.9 (2)
O2—S1—C5109.20 (9)C2—C1—H1A110.00
O1—S1—N1103.40 (8)C2—C1—H1B109.00
O1—S1—C5109.12 (9)C2—C1—H1C109.00
N1—S1—C5105.77 (8)H1A—C1—H1B109.00
S1—N1—C8123.08 (13)H1A—C1—H1C109.00
S1—N1—H1118.00H1B—C1—H1C109.00
C8—N1—H1118.00C2—C3—H3119.00
C1—C2—C3120.9 (2)C4—C3—H3119.00
C1—C2—C7121.6 (2)C3—C4—H4120.00
C3—C2—C7117.5 (2)C5—C4—H4120.00
C2—C3—C4121.8 (2)C5—C6—H6120.00
C3—C4—C5119.5 (2)C7—C6—H6120.00
C4—C5—C6119.8 (2)C2—C7—H7119.00
S1—C5—C4120.43 (17)C6—C7—H7119.00
S1—C5—C6119.78 (15)C9—C10—H10115.00
C5—C6—C7119.5 (2)C11—C10—H10115.00
C2—C7—C6121.9 (2)C11—C12—H12119.00
N1—C8—C9115.33 (15)C13—C12—H12119.00
O3—C8—N1120.79 (17)C12—C13—H13120.00
O3—C8—C9123.88 (17)C14—C13—H13120.00
C10—C9—C17124.16 (16)C13—C14—H14120.00
C8—C9—C10115.24 (16)C15—C14—H14120.00
C8—C9—C17120.42 (15)C14—C15—H15120.00
C9—C10—C11130.45 (17)C16—C15—H15120.00
C12—C11—C16117.83 (18)C11—C16—H16120.00
C10—C11—C12117.32 (17)C15—C16—H16120.00
C10—C11—C16124.79 (17)C17—C18—H18119.00
C11—C12—C13121.2 (2)C19—C18—H18119.00
C12—C13—C14120.0 (2)C19—C20—H20119.00
C13—C14—C15120.0 (2)C21—C20—H20119.00
C14—C15—C16120.4 (2)C20—C21—H21120.00
C11—C16—C15120.46 (19)C22—C21—H21120.00
C18—C17—C22118.86 (17)C17—C22—H22120.00
C9—C17—C18122.21 (16)C21—C22—H22120.00
C9—C17—C22118.87 (17)C19—C23—H23A109.00
C17—C18—C19121.81 (17)C19—C23—H23B109.00
C18—C19—C23121.31 (19)C19—C23—H23C109.00
C20—C19—C23121.30 (19)H23A—C23—H23B109.00
C18—C19—C20117.38 (18)H23A—C23—H23C109.00
C19—C20—C21121.7 (2)H23B—C23—H23C110.00
O2—S1—N1—C851.45 (17)C17—C9—C10—C11−4.3 (3)
O1—S1—N1—C8179.65 (15)C8—C9—C17—C18−85.9 (2)
C5—S1—N1—C8−65.69 (17)C8—C9—C17—C2296.9 (2)
O2—S1—C5—C4−22.48 (19)C10—C9—C17—C1899.4 (2)
O1—S1—C5—C4−155.02 (16)C10—C9—C17—C22−77.8 (2)
N1—S1—C5—C494.32 (17)C9—C10—C11—C12158.7 (2)
O2—S1—C5—C6156.34 (16)C9—C10—C11—C16−24.1 (3)
O1—S1—C5—C623.79 (19)C10—C11—C12—C13178.6 (2)
N1—S1—C5—C6−86.87 (18)C16—C11—C12—C131.1 (3)
S1—N1—C8—C9−175.81 (13)C10—C11—C16—C15−177.9 (2)
S1—N1—C8—O33.5 (3)C12—C11—C16—C15−0.8 (3)
C1—C2—C3—C4179.8 (2)C11—C12—C13—C14−0.4 (4)
C3—C2—C7—C61.3 (3)C12—C13—C14—C15−0.7 (4)
C1—C2—C7—C6−179.7 (2)C13—C14—C15—C161.1 (4)
C7—C2—C3—C4−1.2 (4)C14—C15—C16—C11−0.3 (3)
C2—C3—C4—C5−0.4 (4)C9—C17—C18—C19−175.89 (17)
C3—C4—C5—C61.8 (3)C22—C17—C18—C191.3 (3)
C3—C4—C5—S1−179.38 (19)C9—C17—C22—C21174.5 (2)
S1—C5—C6—C7179.47 (17)C18—C17—C22—C21−2.8 (3)
C4—C5—C6—C7−1.7 (3)C17—C18—C19—C201.5 (3)
C5—C6—C7—C20.2 (3)C17—C18—C19—C23−179.25 (18)
O3—C8—C9—C1012.7 (3)C18—C19—C20—C21−3.0 (3)
O3—C8—C9—C17−162.47 (18)C23—C19—C20—C21177.8 (2)
N1—C8—C9—C10−168.01 (17)C19—C20—C21—C221.6 (4)
N1—C8—C9—C1716.8 (2)C20—C21—C22—C171.4 (4)
C8—C9—C10—C11−179.30 (19)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings C11–C16 and C17–C22, respectively.

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.313.038 (2)143
C21—H21···O2ii0.932.573.468 (4)163
C16—H16···Cg30.932.883.617 (2)137
C18—H18···Cg2iii0.932.833.646 (2)168

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1.

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Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography