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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o366-o367
https://doi.org/10.1107/S2056989015008154

Crystal structure of ethyl 2-amino-4-(4-meth­­oxy­phen­yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl­ate

Mohamed Bakhouch,a* Abdelali Kerbal,a Mohamed El Yazidi,a Mohamed Saadib and Lahcen El Ammarib

aDépartement de Chimie, Faculté des Sciences, Dhar Mehraz, BP 1796 Atlas, 30000 Fes, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: m.bakhouch@yahoo.fr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 9 April 2015; accepted 23 April 2015; online 30 April 2015)

The mol­ecule of the title compound, C21H19NO4S, features a fused ring system whereby a five-membered ring is flanked by two six-membered rings. This is linked to an ethyl 3-carboxyl­ate group and to a meth­oxy­benzene group. The fused-ring system is quasi-planar, with the greatest deviation from the mean plane being 0.131 (1) Å for the methine C atom. The plane through the meth­oxy­benzene ring is nearly perpendicular to that through the fused-ring system, as indicated by the dihedral angle of 85.72 (6)°. An intra­molecular N—H⋯O hydrogen bond is noted. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming layers that stack along the a axis.

CCDC reference: 1061576

Similar articles

1. Related literature

For biological properties of substituted 2-amino-4-aryl-4H-pyran derivatives, see: Panda et al. (1997[Panda, D., Singh, J. P. & Wilson, L. (1997). J. Biol. Chem. 272, 7681-7687.]); Mungra et al. (2011[Mungra, D. C., Patel, M. P., Rajani, D. P. & Patel, R. G. (2011). Eur. J. Med. Chem. 46, 4192-4200.]). For the reactivity of (Z)-2-aryl­idenebenzo[b]thio­phen-3(2H)-ones (thio­aurones), see: Boughaleb et al. (2010[Boughaleb, A., Al houari, G., Bennani, B., Daoudi, M., Garrigues, B., Kerbal, A. & El yazidi, M. (2010). J. Soc. Chim. Tunisie, 12, 109-115.]; 2011[Boughaleb, A., Akhazzane, M., Alhouari, G., Bennani, B., Daoudi, M., Garrigues, B., Kerbal, A. & El yazidi, M. (2011). J. Soc. Chim. Tunisie, 13, 117-122.]); Bakhouch et al. (2014[Bakhouch, M., Al Houari, G., El Yazidi, M., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o587.], 2015[Bakhouch, M., Al Houari, G., Daoudi, M., Kerbal, A. & El Yazidi, M. (2015). Med. J. Chem. 4, 9-17.]). For the preparation of the title compound, using condensation reactions, see: Daisley et al. (1982[Daisley, R. W., Elagbar, Z. A. & Walker, J. (1982). J. Heterocycl. Chem. 19, 1013-1016.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H19NO4S

  • Mr = 381.43

  • Monoclinic, P 21 /c

  • a = 11.8355 (7) Å

  • b = 18.6222 (11) Å

  • c = 9.0110 (5) Å

  • β = 106.502 (2)°

  • V = 1904.25 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 296 K

  • 0.42 × 0.31 × 0.26 mm

2.2. Data collection

  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1995[Sheldrick, G. M. (1995). SADABS. University of Göttingen, Germany.]) Tmin = 0.673, Tmax = 0.746

  • 38870 measured reflections

  • 5347 independent reflections

  • 4118 reflections with I > 2σ(I)

  • Rint = 0.031

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.130

  • S = 1.06

  • 5347 reflections

  • 244 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2B⋯O2 0.86 2.08 2.6903 (16) 128
N2—H2A⋯O2i 0.86 2.17 2.9964 (16) 161
N2—H2B⋯O4ii 0.86 2.38 3.0908 (17) 140
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1061576

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015008154/tk5366sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015008154/tk5366Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015008154/tk5366Isup3.cml

checkCIF report


Comment top

Substituted 2-amino-4-aryl-4H-pyran derivatives are an important class of heterocyclic compounds, which frequently exhibit a wide range of biological properties viz. antiproliferative, antitubercular activities (Panda et al., 1997; Mungra et al., 2011). Thus, in view of the large spectrum of applications of these compounds and in continuation of ongoing research focused on the reactivity of the (Z)-2-arylidenebenzo[b]thiophen- 3(2H)-ones (thioaurones) (Boughaleb et al., 2010; 2011; Bakhouch et al., 2014; 2015), the title compound was investigated This was prepared by the the action of ethyl cyanoacetate on (Z)-2-(4- methoxybenzylidene)benzo[b]thiophen-3(2H)-one (Daisley et al., 1982). The subsequent tautomeric transformation gives rise to ethyl 2-amino-4-(4-methoxyphenyl)-4H-1-benzothieno[3,2-b]pyran-3- carboxylate.

The molecule of the title compound is formed by three fused rings linked to an ethyl-3-carboxylate group and to a methoxybenzene group as shown in Fig. 1. The three fused rings (S1C1 to C11 O1) are nearly coplanar, with the maximum deviation from the mean plane being -0.131 (1) Å at C10, and makes a dihedral angle of 85.72 (6)° with the plans through this attached methoxyphenyl group.

In the crystal, the molecules are linked by N—H···O hydrogen bonds as shown in Fig. 2 and Table 1.

Related literature top

For biological properties of substituted 2-amino-4-aryl-4H-pyran derivatives, see: Panda et al. (1997); Mungra et al. (2011). For the reactivity of the (Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones (thioaurones), see: Boughaleb et al. (2010; 2011); Bakhouch et al. (2014, 2015). For the preparation of the title compound, using condensation reactions, see: Daisley et al. (1982).

Experimental top

In a 100 ml flask equipped with a condenser was dissolved 4 mmol of (Z)-2-(4-methoxybenzylidene)-1-benzo[b]thiophen-3(2H)-one and 5 mmol of ethyl cyanoacetate in 30 ml of ethanol. Then, 1 ml of piperidine was added, and the reaction mixture was refluxed for 6 h. Thin layer chromatography revealed the formation of a single product. The organic phase was evaporated under reduced pressure. The resulting residue was recrystallized from ethanol by slow evaporation (Yield: 28%; m.pt: 395 K).

Refinement top

H atoms were located in a difference map and treated as riding with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2–1.5 Ueq(C) and Uiso(H) = 1.2 Ueq(N). Two reflections, i.e. (1 0 0) and (1 1 0), were omitted from the final refinement owing to poor agreement.

Structure description top

Substituted 2-amino-4-aryl-4H-pyran derivatives are an important class of heterocyclic compounds, which frequently exhibit a wide range of biological properties viz. antiproliferative, antitubercular activities (Panda et al., 1997; Mungra et al., 2011). Thus, in view of the large spectrum of applications of these compounds and in continuation of ongoing research focused on the reactivity of the (Z)-2-arylidenebenzo[b]thiophen- 3(2H)-ones (thioaurones) (Boughaleb et al., 2010; 2011; Bakhouch et al., 2014; 2015), the title compound was investigated This was prepared by the the action of ethyl cyanoacetate on (Z)-2-(4- methoxybenzylidene)benzo[b]thiophen-3(2H)-one (Daisley et al., 1982). The subsequent tautomeric transformation gives rise to ethyl 2-amino-4-(4-methoxyphenyl)-4H-1-benzothieno[3,2-b]pyran-3- carboxylate.

The molecule of the title compound is formed by three fused rings linked to an ethyl-3-carboxylate group and to a methoxybenzene group as shown in Fig. 1. The three fused rings (S1C1 to C11 O1) are nearly coplanar, with the maximum deviation from the mean plane being -0.131 (1) Å at C10, and makes a dihedral angle of 85.72 (6)° with the plans through this attached methoxyphenyl group.

In the crystal, the molecules are linked by N—H···O hydrogen bonds as shown in Fig. 2 and Table 1.

For biological properties of substituted 2-amino-4-aryl-4H-pyran derivatives, see: Panda et al. (1997); Mungra et al. (2011). For the reactivity of the (Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones (thioaurones), see: Boughaleb et al. (2010; 2011); Bakhouch et al. (2014, 2015). For the preparation of the title compound, using condensation reactions, see: Daisley et al. (1982).

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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Plot of the molecule of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
2-Amino-4-(4-methoxyphenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate top
Crystal data top
C21H19NO4SF(000) = 800
Mr = 381.43Dx = 1.330 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5347 reflections
a = 11.8355 (7) Åθ = 2.2–29.6°
b = 18.6222 (11) ŵ = 0.20 mm−1
c = 9.0110 (5) ÅT = 296 K
β = 106.502 (2)°Block, colourless
V = 1904.25 (19) Å30.42 × 0.31 × 0.26 mm
Z = 4
Data collection top
Bruker X8 APEX
diffractometer		5347 independent reflections
Radiation source: fine-focus sealed tube4118 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 29.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)		h = −16→16
Tmin = 0.673, Tmax = 0.746k = −25→25
38870 measured reflectionsl = −8→12
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.5166P]
where P = (Fo2 + 2Fc2)/3
5347 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C21H19NO4SV = 1904.25 (19) Å3
Mr = 381.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8355 (7) ŵ = 0.20 mm−1
b = 18.6222 (11) ÅT = 296 K
c = 9.0110 (5) Å0.42 × 0.31 × 0.26 mm
β = 106.502 (2)°
Data collection top
Bruker X8 APEX
diffractometer		5347 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)		4118 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 0.746Rint = 0.031
38870 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.06Δρmax = 0.25 e Å−3
5347 reflectionsΔρmin = −0.27 e Å−3
244 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
xyzUiso*/Ueq
C10.54915 (13)0.61283 (8)0.9681 (2)0.0525 (4)
C20.46963 (16)0.61032 (10)1.0560 (3)0.0699 (5)
H20.40060.58371.02310.084*
C30.4953 (2)0.64792 (11)1.1919 (3)0.0816 (6)
H30.44340.64631.25220.098*
C40.5973 (2)0.68840 (11)1.2411 (3)0.0830 (7)
H40.61260.71371.33370.100*
C50.67644 (18)0.69176 (9)1.1550 (2)0.0666 (5)
H50.74450.71931.18850.080*
C60.65300 (13)0.65344 (7)1.01733 (18)0.0460 (3)
C70.72073 (12)0.64514 (7)0.90952 (16)0.0412 (3)
C80.88161 (12)0.67389 (7)0.81926 (15)0.0394 (3)
C90.84330 (12)0.62861 (7)0.69542 (15)0.0405 (3)
C100.73518 (13)0.58116 (7)0.67067 (16)0.0434 (3)
H100.68220.59110.56750.052*
C110.67418 (12)0.60232 (7)0.78831 (17)0.0436 (3)
C120.76078 (13)0.50065 (7)0.68312 (15)0.0416 (3)
C130.83473 (14)0.47133 (8)0.81661 (16)0.0484 (3)
H130.87410.50160.89680.058*
C140.85118 (15)0.39799 (8)0.83308 (19)0.0537 (4)
H140.90090.37920.92390.064*
C150.79345 (14)0.35251 (8)0.7142 (2)0.0517 (4)
C160.72156 (16)0.38052 (9)0.5795 (2)0.0587 (4)
H160.68390.35030.49830.070*
C170.70549 (15)0.45444 (9)0.56549 (18)0.0547 (4)
H170.65610.47320.47430.066*
C180.7396 (2)0.23146 (10)0.6393 (4)0.0980 (8)
H18A0.76230.18320.67190.147*
H18B0.74730.23890.53720.147*
H18C0.65920.23920.63840.147*
C190.90696 (14)0.62770 (7)0.58012 (16)0.0462 (3)
C200.9195 (2)0.56999 (10)0.3491 (2)0.0703 (5)
H20A1.00170.55790.39600.084*
H20B0.91560.61330.28810.084*
C210.8570 (3)0.50952 (12)0.2497 (2)0.0897 (7)
H21A0.89350.50040.16910.135*
H21B0.77580.52230.20450.135*
H21C0.86140.46720.31180.135*
N20.97404 (11)0.71791 (7)0.84860 (15)0.0496 (3)
H2A0.99070.74450.93000.060*
H2B1.01710.71970.78620.060*
O10.82701 (9)0.68022 (6)0.93374 (12)0.0483 (2)
O20.99346 (11)0.66385 (6)0.58006 (13)0.0556 (3)
O30.85945 (12)0.58024 (6)0.46707 (12)0.0600 (3)
O40.81361 (12)0.28053 (6)0.74361 (18)0.0727 (4)
S10.53964 (4)0.56789 (3)0.79591 (6)0.06281 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0427 (7)0.0455 (7)0.0715 (10)0.0012 (6)0.0199 (7)0.0062 (7)
C20.0508 (9)0.0631 (10)0.1059 (15)−0.0028 (8)0.0388 (10)0.0102 (10)
C30.0858 (14)0.0717 (12)0.1146 (18)−0.0017 (10)0.0725 (14)0.0004 (12)
C40.1067 (16)0.0694 (12)0.1008 (16)−0.0151 (11)0.0746 (14)−0.0204 (11)
C50.0791 (12)0.0565 (9)0.0813 (12)−0.0179 (8)0.0506 (10)−0.0193 (9)
C60.0471 (7)0.0364 (6)0.0608 (9)−0.0011 (5)0.0253 (6)0.0012 (6)
C70.0417 (6)0.0352 (6)0.0491 (7)−0.0029 (5)0.0169 (6)−0.0019 (5)
C80.0445 (6)0.0358 (6)0.0414 (7)0.0006 (5)0.0181 (5)0.0004 (5)
C90.0516 (7)0.0336 (6)0.0379 (7)0.0003 (5)0.0150 (6)0.0020 (5)
C100.0501 (7)0.0408 (6)0.0350 (6)−0.0021 (5)0.0053 (5)−0.0008 (5)
C110.0412 (6)0.0392 (6)0.0483 (8)−0.0011 (5)0.0093 (6)0.0010 (5)
C120.0507 (7)0.0392 (6)0.0347 (6)−0.0062 (5)0.0120 (5)−0.0052 (5)
C130.0635 (9)0.0413 (7)0.0368 (7)−0.0032 (6)0.0086 (6)−0.0061 (5)
C140.0648 (9)0.0446 (8)0.0515 (9)0.0040 (7)0.0162 (7)0.0033 (6)
C150.0564 (8)0.0375 (7)0.0727 (10)−0.0054 (6)0.0370 (8)−0.0095 (6)
C160.0681 (10)0.0511 (8)0.0597 (10)−0.0175 (7)0.0230 (8)−0.0239 (7)
C170.0639 (9)0.0534 (8)0.0417 (8)−0.0105 (7)0.0068 (7)−0.0106 (6)
C180.0876 (14)0.0439 (9)0.175 (3)−0.0152 (9)0.0570 (16)−0.0330 (13)
C190.0666 (9)0.0370 (6)0.0378 (7)0.0055 (6)0.0192 (6)0.0035 (5)
C200.1086 (16)0.0698 (11)0.0429 (9)0.0043 (10)0.0384 (10)−0.0031 (7)
C210.146 (2)0.0812 (14)0.0477 (10)−0.0027 (14)0.0360 (12)−0.0168 (9)
N20.0545 (7)0.0493 (6)0.0527 (7)−0.0134 (5)0.0276 (6)−0.0125 (5)
O10.0499 (5)0.0532 (6)0.0486 (6)−0.0163 (4)0.0248 (4)−0.0154 (4)
O20.0742 (7)0.0480 (6)0.0545 (6)−0.0039 (5)0.0345 (6)0.0020 (5)
O30.0858 (8)0.0595 (6)0.0406 (6)−0.0071 (6)0.0277 (6)−0.0085 (5)
O40.0800 (8)0.0368 (5)0.1128 (11)−0.0022 (5)0.0458 (8)−0.0092 (6)
S10.0452 (2)0.0688 (3)0.0704 (3)−0.01563 (18)0.00995 (19)−0.0072 (2)
Geometric parameters (Å, º) top
C1—C21.393 (2)C13—C141.382 (2)
C1—C61.404 (2)C13—H130.9300
C1—S11.7381 (18)C14—C151.384 (2)
C2—C31.367 (3)C14—H140.9300
C2—H20.9300C15—C161.372 (3)
C3—C41.385 (3)C15—O41.3742 (18)
C3—H30.9300C16—C171.390 (2)
C4—C51.377 (2)C16—H160.9300
C4—H40.9300C17—H170.9300
C5—C61.389 (2)C18—O41.420 (3)
C5—H50.9300C18—H18A0.9600
C6—C71.4327 (19)C18—H18B0.9600
C7—C111.3381 (19)C18—H18C0.9600
C7—O11.3786 (16)C19—O21.2255 (19)
C8—N21.3319 (17)C19—O31.3451 (18)
C8—O11.3691 (15)C20—O31.450 (2)
C8—C91.3691 (18)C20—C211.497 (3)
C9—C191.4464 (19)C20—H20A0.9700
C9—C101.5185 (19)C20—H20B0.9700
C10—C111.495 (2)C21—H21A0.9600
C10—C121.5273 (19)C21—H21B0.9600
C10—H100.9800C21—H21C0.9600
C11—S11.7360 (14)N2—H2A0.8600
C12—C171.3778 (19)N2—H2B0.8600
C12—C131.383 (2)
C2—C1—C6120.72 (17)C12—C13—H13119.4
C2—C1—S1127.51 (14)C13—C14—C15119.88 (15)
C6—C1—S1111.75 (12)C13—C14—H14120.1
C3—C2—C1118.55 (17)C15—C14—H14120.1
C3—C2—H2120.7C16—C15—O4124.87 (15)
C1—C2—H2120.7C16—C15—C14119.85 (14)
C2—C3—C4121.17 (17)O4—C15—C14115.28 (16)
C2—C3—H3119.4C15—C16—C17119.43 (14)
C4—C3—H3119.4C15—C16—H16120.3
C5—C4—C3120.97 (19)C17—C16—H16120.3
C5—C4—H4119.5C12—C17—C16121.70 (15)
C3—C4—H4119.5C12—C17—H17119.1
C4—C5—C6118.99 (18)C16—C17—H17119.1
C4—C5—H5120.5O4—C18—H18A109.5
C6—C5—H5120.5O4—C18—H18B109.5
C5—C6—C1119.60 (14)H18A—C18—H18B109.5
C5—C6—C7130.75 (14)O4—C18—H18C109.5
C1—C6—C7109.63 (13)H18A—C18—H18C109.5
C11—C7—O1123.86 (12)H18B—C18—H18C109.5
C11—C7—C6115.96 (13)O2—C19—O3122.02 (13)
O1—C7—C6120.17 (12)O2—C19—C9126.84 (13)
N2—C8—O1109.53 (11)O3—C19—C9111.15 (13)
N2—C8—C9127.16 (12)O3—C20—C21105.98 (17)
O1—C8—C9123.31 (12)O3—C20—H20A110.5
C8—C9—C19118.24 (12)C21—C20—H20A110.5
C8—C9—C10123.25 (12)O3—C20—H20B110.5
C19—C9—C10118.48 (12)C21—C20—H20B110.5
C11—C10—C9107.39 (11)H20A—C20—H20B108.7
C11—C10—C12109.41 (11)C20—C21—H21A109.5
C9—C10—C12114.78 (12)C20—C21—H21B109.5
C11—C10—H10108.4H21A—C21—H21B109.5
C9—C10—H10108.4C20—C21—H21C109.5
C12—C10—H10108.4H21A—C21—H21C109.5
C7—C11—C10124.48 (13)H21B—C21—H21C109.5
C7—C11—S1110.95 (11)C8—N2—H2A120.0
C10—C11—S1124.31 (10)C8—N2—H2B120.0
C17—C12—C13117.87 (13)H2A—N2—H2B120.0
C17—C12—C10121.04 (13)C8—O1—C7116.40 (10)
C13—C12—C10120.98 (12)C19—O3—C20117.08 (14)
C14—C13—C12121.25 (13)C15—O4—C18117.34 (17)
C14—C13—H13119.4C11—S1—C191.71 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.862.082.6903 (16)128
N2—H2A···O2i0.862.172.9964 (16)161
N2—H2B···O4ii0.862.383.0908 (17)140
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.862.082.6903 (16)128
N2—H2A···O2i0.862.172.9964 (16)161
N2—H2B···O4ii0.862.383.0908 (17)140
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, y+1/2, −z+3/2.
 

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray intensity measurements.

References

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o366-o367
https://doi.org/10.1107/S2056989015008154
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