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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 70| Part 7| July 2014| Page o775
https://doi.org/10.1107/S1600536814013245

2-[(E)-1,1-Dioxo-2-(2,4,5-tri­fluoro­benz­yl)-3,4-di­hydro-2H-1,2-benzo­thia­zin-4-yl­­idene]acetic acid

Shaojuan Zhu,a Shagufta Parveena and Changjin Zhua*

aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
*Correspondence e-mail: zcj@bit.edu.cn

(Received 20 May 2014; accepted 6 June 2014; online 14 June 2014)

In the asymmetric unit of the title compound, C17H12F3NO4S, there are two conformationally similar mol­ecules in which the heterocyclic thia­zine ring adopts a half-chair conformation, with the dihedral angle between the two benzene rings being 24.84 (8) and 37.42 (8)°. In the crystal, the mol­ecules form dimers through cyclic carb­oxy­lic acid O—H⋯O hydrogen-bonding associations [graph set R22(8)] and are extended into chains along [101] through weak C—H⋯Osulfin­yl hydrogen bonds [graph set R22(14)]..

CCDC reference: 1007103

Related literature

For pharmaceutical and biological properties of 1,2-benzo­thia­zines, see: Zia-ur-Rehman et al. (2005[Zia-ur-Rehman, M., Anwar, J. & Ahmad, S. (2005). Bull. Korean Chem. Soc. 26, 1771-1775.]); Lombardino et al. (1971[Lombardino, J. G., Wiseman, E. H. & McLamore, W. M. (1971). J. Med. Chem. 14, 1171-1175.]); Bihovsky et al. (2004[Bihovsky, R., Tao, M., Mallamo, J. P. & Wells, G. J. (2004). Bioorg. Med. Chem. Lett. 14, 1035-1038.]); For synthetic details of the title compound, see: Parveen et al. (2014b[Parveen, S., Hussain, S., Zhu, S., Qin, X., Hao, X., Zhang, S., Lu, J. & Zhu, C. (2014b). RSC. Adv. 4, 21134-21140.]). For related structures, see: Yang et al. (2012[Yang, Y., Yu, Y. & Zhu, C. (2012). Acta Cryst. E68, o1364.]); Parveen et al. (2014a[Parveen, S., Hussain, S., Zhu, S., Hao, X. & Zhu, C. (2014a). Acta Cryst. E70, o627.]). For graph-set analysis, see: Etter et al. 1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C17H12F3NO4S

  • Mr = 383.34

  • Triclinic, [P \overline 1]

  • a = 8.0028 (10) Å

  • b = 14.249 (2) Å

  • c = 15.076 (2) Å

  • α = 104.631 (8)°

  • β = 99.915 (6)°

  • γ = 104.237 (6)°

  • V = 1561.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 153 K

  • 0.31 × 0.26 × 0.18 mm
Data collection

  • Rigaku AFC10/Saturn724+ CCD-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.932, Tmax = 0.964

  • 20894 measured reflections

  • 8293 independent reflections

  • 6954 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.114

  • S = 1.00

  • 8293 reflections

  • 477 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3O⋯O8i 0.85 (3) 1.86 (3) 2.7063 (17) 172 (3)
O7—H7O⋯O4ii 0.92 (3) 1.73 (3) 2.6473 (17) 177 (2)
C15—H15⋯O6 0.95 2.34 3.267 (2) 165
C32—H32⋯O2 0.95 2.61 3.539 (2) 165
Symmetry codes: (i) x+1, y, z-1; (ii) x-1, y, z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); data reduction: CrystalClear; 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: DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2008[Rigaku (2008). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information

CCDC reference: 1007103

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536814013245/zs2301sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013245/zs2301Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013245/zs2301Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013245/zs2301Isup4.cml

checkCIF report


Comment top

1,2-Benzothiazine-1,1-dioxide derivatives are reported as having anti- inflammatory and anti-bacterial activities (Lombardino et al., 1971) while some of its derivatives have been found to be calpain 1 inhibitors (Bihovsky et al., 2004). More recently, its derivatives were reported as aldose reductase inhibitors (Parveen et al., 2014b). Herein, we report the structure of the title derivative, C17H12F3NO4S, which is the E isomer of the previously published isomer 2-[(Z)-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4- dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid (Parveen et al., 2014a).

In the title compound, there are two conformationally similar molecules (A and B) in the asymmetric unit (Fig. 1). The dihedral angles between mean plane of the two benzene rings [(C1—C6) and (C10—C15) in A and (C18–C23) and (C27–C32) in B] are 37.42 (8) and 24.84 (7)°, respectively. These values compare with 43.28 (9)° in the Z isomer (Parveen et al., 2014a). The heterocyclic thiazine ring adopts a half-chair conformation. The acetic acid substituent groups show only minor conformational differences: torsion angles C8—C7—C16—C17 and C7—C16—C17—O3 [169.7 (16) and 174.59 (17)°, respectively] in A campare with C25—C24— C33—C34 and C24—C33—C34—O7 [-179.25 (16) and -168.18 (17), respectively] in B.

In the crystal the molecules form centrosymmetric dimers through intermolecular cyclic carboxylic acid O—H···O hydrogen-bonding associations [graph set R22(8) (Etter et al., 1990)]. These dimers form one-dimensional chains which extend along [101] (Fig. 2), through weak duplex C—H···Osulfinyl hydrogen-bonding associations (Table 1) [graph set R22(14)].

Related literature top

For pharmaceutical and biological properties of 1,2-benzothiazines, see: Zia-ur-Rehman et al. (2005); Lombardino et al. (1971); Bihovsky et al. (2004); For synthetic details of the title compound, see: Parveen et al. (2014b). For related structures, see: Yang et al. (2012); Parveen et al. (2014a). For graph-set analysis, see: Etter et al. 1990).

Experimental top

A mixture of E-2-[2-(2,4,5-Trifluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin- 4(3H)-ylidene]acetic acid methyl ester (0.5 mmol), 10 M hydrochloric acid (8 mL), and 1,4-dioxane (5 mL) was refluxed at 60°C for 2 h. The crude product obtained was washed with cold water (3 times, 10 mL) and purified by flash chromatography with CH2Cl2 and methanol (100:1) as eluent, which afforded a white solid product on concentration under vacuum. Recrystallization from ethanol gave crystals of the title compound suitable for the X-ray analysis (yield = 60%).

Refinement top

H atoms bonded to O1 and O3 were located from a difference-Fourier map and were refined freely. The remaining H atoms were positioned geometrically, with C—H = 0.95 and 0.99 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Structure description top

1,2-Benzothiazine-1,1-dioxide derivatives are reported as having anti- inflammatory and anti-bacterial activities (Lombardino et al., 1971) while some of its derivatives have been found to be calpain 1 inhibitors (Bihovsky et al., 2004). More recently, its derivatives were reported as aldose reductase inhibitors (Parveen et al., 2014b). Herein, we report the structure of the title derivative, C17H12F3NO4S, which is the E isomer of the previously published isomer 2-[(Z)-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4- dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid (Parveen et al., 2014a).

In the title compound, there are two conformationally similar molecules (A and B) in the asymmetric unit (Fig. 1). The dihedral angles between mean plane of the two benzene rings [(C1—C6) and (C10—C15) in A and (C18–C23) and (C27–C32) in B] are 37.42 (8) and 24.84 (7)°, respectively. These values compare with 43.28 (9)° in the Z isomer (Parveen et al., 2014a). The heterocyclic thiazine ring adopts a half-chair conformation. The acetic acid substituent groups show only minor conformational differences: torsion angles C8—C7—C16—C17 and C7—C16—C17—O3 [169.7 (16) and 174.59 (17)°, respectively] in A campare with C25—C24— C33—C34 and C24—C33—C34—O7 [-179.25 (16) and -168.18 (17), respectively] in B.

In the crystal the molecules form centrosymmetric dimers through intermolecular cyclic carboxylic acid O—H···O hydrogen-bonding associations [graph set R22(8) (Etter et al., 1990)]. These dimers form one-dimensional chains which extend along [101] (Fig. 2), through weak duplex C—H···Osulfinyl hydrogen-bonding associations (Table 1) [graph set R22(14)].

For pharmaceutical and biological properties of 1,2-benzothiazines, see: Zia-ur-Rehman et al. (2005); Lombardino et al. (1971); Bihovsky et al. (2004); For synthetic details of the title compound, see: Parveen et al. (2014b). For related structures, see: Yang et al. (2012); Parveen et al. (2014a). For graph-set analysis, see: Etter et al. 1990).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: CrystalStructure (Rigaku, 2008).

Figures top
[Figure 1] Fig. 1. The molecular conformation and atom numbering scheme for the two independent molecules (A and B) of the title compound in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen-bonding interactions (O—H···O and C—H···O), shown as dashed lines, in the one-dimensional chain structure of the title compound. H atoms non–participating in hydrogen-bonding are omitted for clarity.
2-[(E)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid top
Crystal data top
C17H12F3NO4SZ = 4
Mr = 383.34F(000) = 784
Triclinic, P1Dx = 1.631 Mg m−3
a = 8.0028 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.249 (2) ÅCell parameters from 5221 reflections
c = 15.076 (2) Åθ = 2.4–29.1°
α = 104.631 (8)°µ = 0.27 mm−1
β = 99.915 (6)°T = 153 K
γ = 104.237 (6)°Prism, colourless
V = 1561.2 (4) Å30.31 × 0.26 × 0.18 mm
Data collection top
Rigaku AFC10/Saturn724+ CCD-detector
diffractometer		8293 independent reflections
Radiation source: Rotating Anode6954 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 28.5714 pixels mm-1θmax = 29.1°, θmin = 2.7°
φ and ω scansh = −10→10
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)		k = −19→19
Tmin = 0.932, Tmax = 0.964l = −20→20
20894 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.061P)2 + 0.226P]
where P = (Fo2 + 2Fc2)/3
8293 reflections(Δ/σ)max = 0.001
477 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C17H12F3NO4Sγ = 104.237 (6)°
Mr = 383.34V = 1561.2 (4) Å3
Triclinic, P1Z = 4
a = 8.0028 (10) ÅMo Kα radiation
b = 14.249 (2) ŵ = 0.27 mm−1
c = 15.076 (2) ÅT = 153 K
α = 104.631 (8)°0.31 × 0.26 × 0.18 mm
β = 99.915 (6)°
Data collection top
Rigaku AFC10/Saturn724+ CCD-detector
diffractometer		8293 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)		6954 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.964Rint = 0.030
20894 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.32 e Å−3
8293 reflectionsΔρmin = −0.43 e Å−3
477 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
S10.73455 (5)0.69761 (3)0.55702 (3)0.02391 (10)
S20.50292 (5)0.87262 (3)0.79867 (3)0.02531 (10)
F10.58349 (14)0.89772 (9)0.31143 (8)0.0450 (3)
F20.03716 (14)0.93851 (8)0.35868 (8)0.0423 (3)
F30.08711 (14)0.88184 (8)0.51527 (8)0.0391 (3)
F40.45408 (14)0.54711 (9)0.91587 (8)0.0431 (3)
F51.01396 (15)0.50243 (9)0.90295 (8)0.0469 (3)
F61.06588 (13)0.63243 (8)0.80223 (8)0.0387 (3)
O10.63170 (15)0.60907 (9)0.57395 (8)0.0311 (3)
O20.82039 (16)0.78775 (9)0.63550 (8)0.0328 (3)
O40.99668 (15)0.69914 (10)0.24217 (8)0.0337 (3)
O30.78052 (17)0.70022 (12)0.12780 (9)0.0417 (3)
O50.63875 (15)0.96931 (9)0.83329 (9)0.0335 (3)
O60.44968 (17)0.82015 (11)0.69925 (8)0.0386 (3)
O70.26182 (16)0.72184 (10)1.15812 (9)0.0334 (3)
O80.06107 (15)0.74619 (10)1.05181 (9)0.0379 (3)
N10.60349 (16)0.72401 (9)0.47719 (9)0.0224 (3)
N20.56830 (16)0.79812 (10)0.85392 (9)0.0232 (3)
C10.89250 (19)0.65910 (11)0.49927 (11)0.0233 (3)
C21.0447 (2)0.65398 (12)0.55604 (13)0.0298 (3)
H21.06950.68010.62300.036*
C31.1599 (2)0.61036 (13)0.51375 (14)0.0344 (4)
H31.26700.60920.55150.041*
C41.1179 (2)0.56859 (13)0.41639 (14)0.0341 (4)
H41.19120.53340.38790.041*
C50.9703 (2)0.57747 (12)0.35992 (13)0.0286 (3)
H50.94520.54950.29310.034*
C60.85747 (19)0.62700 (11)0.39983 (11)0.0234 (3)
C70.70501 (19)0.64394 (11)0.34115 (11)0.0232 (3)
C80.54758 (19)0.64252 (11)0.38476 (11)0.0238 (3)
H8A0.45090.65330.34170.029*
H8B0.50170.57550.39400.029*
C90.6528 (2)0.82967 (12)0.47205 (12)0.0273 (3)
H9A0.72810.83520.42680.033*
H9B0.72240.87740.53500.033*
C100.4876 (2)0.85800 (11)0.44047 (11)0.0237 (3)
C110.4596 (2)0.89144 (12)0.36246 (12)0.0291 (3)
C120.3112 (2)0.91996 (13)0.33337 (12)0.0320 (4)
H120.29650.94300.27950.038*
C130.1865 (2)0.91365 (12)0.38516 (12)0.0285 (3)
C140.2105 (2)0.88278 (12)0.46446 (12)0.0266 (3)
C150.3584 (2)0.85423 (11)0.49217 (11)0.0245 (3)
H150.37270.83190.54650.029*
C160.6974 (2)0.66706 (12)0.25983 (11)0.0274 (3)
H160.58490.66970.22970.033*
C170.8406 (2)0.68902 (12)0.21090 (11)0.0273 (3)
C180.31608 (19)0.89025 (11)0.83939 (11)0.0224 (3)
C190.2095 (2)0.93054 (13)0.78660 (12)0.0291 (3)
H190.23740.94440.73150.035*
C200.0627 (2)0.95032 (13)0.81459 (12)0.0304 (3)
H20−0.01180.97720.77870.036*
C210.0259 (2)0.93060 (12)0.89503 (12)0.0282 (3)
H21−0.07440.94470.91470.034*
C220.1323 (2)0.89045 (11)0.94806 (11)0.0257 (3)
H220.10430.87871.00380.031*
C230.27989 (18)0.86690 (10)0.92127 (10)0.0199 (3)
C240.39674 (19)0.82390 (11)0.97612 (10)0.0207 (3)
C250.57919 (19)0.83583 (12)0.95578 (10)0.0225 (3)
H25A0.65010.90870.98070.027*
H25B0.64180.79810.98940.027*
C260.4900 (2)0.68674 (12)0.80941 (12)0.0276 (3)
H26A0.45190.67050.73980.033*
H26B0.38430.66160.83240.033*
C270.6278 (2)0.63582 (11)0.83449 (11)0.0237 (3)
C280.6062 (2)0.56868 (12)0.88642 (12)0.0286 (3)
C290.7309 (2)0.52137 (13)0.91045 (13)0.0346 (4)
H290.71130.47520.94610.042*
C300.8843 (2)0.54411 (13)0.88054 (12)0.0316 (4)
C310.9114 (2)0.61120 (12)0.82925 (11)0.0266 (3)
C320.7862 (2)0.65739 (11)0.80590 (11)0.0249 (3)
H320.80710.70370.77050.030*
C330.3679 (2)0.77728 (11)1.04221 (11)0.0242 (3)
H330.46720.75871.06810.029*
C340.2146 (2)0.74921 (11)1.08260 (11)0.0250 (3)
H7O0.168 (3)0.7121 (19)1.1855 (17)0.067 (8)*
H3O0.865 (4)0.720 (2)0.1031 (19)0.077 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02321 (19)0.02732 (19)0.0232 (2)0.00954 (14)0.00707 (15)0.00851 (14)
S20.02388 (19)0.0386 (2)0.0241 (2)0.01631 (16)0.01081 (15)0.01787 (16)
F10.0420 (6)0.0616 (7)0.0486 (7)0.0182 (5)0.0274 (5)0.0332 (6)
F20.0334 (6)0.0458 (6)0.0555 (7)0.0206 (5)0.0046 (5)0.0252 (5)
F30.0347 (5)0.0464 (6)0.0510 (7)0.0214 (5)0.0237 (5)0.0229 (5)
F40.0389 (6)0.0487 (6)0.0551 (7)0.0143 (5)0.0289 (5)0.0267 (5)
F50.0471 (7)0.0532 (7)0.0505 (7)0.0352 (6)0.0067 (5)0.0174 (6)
F60.0234 (5)0.0409 (6)0.0516 (7)0.0125 (4)0.0154 (5)0.0070 (5)
O10.0305 (6)0.0368 (6)0.0326 (6)0.0106 (5)0.0128 (5)0.0184 (5)
O20.0334 (6)0.0353 (6)0.0253 (6)0.0123 (5)0.0042 (5)0.0023 (5)
O40.0260 (6)0.0490 (7)0.0280 (6)0.0065 (5)0.0093 (5)0.0182 (5)
O30.0297 (7)0.0699 (10)0.0330 (7)0.0114 (6)0.0110 (5)0.0304 (7)
O50.0253 (6)0.0410 (7)0.0467 (8)0.0122 (5)0.0143 (5)0.0293 (6)
O60.0427 (7)0.0659 (9)0.0222 (6)0.0336 (7)0.0137 (5)0.0188 (6)
O70.0327 (6)0.0492 (7)0.0321 (7)0.0171 (6)0.0153 (5)0.0269 (6)
O80.0249 (6)0.0608 (8)0.0334 (7)0.0077 (6)0.0080 (5)0.0283 (6)
N10.0209 (6)0.0236 (6)0.0241 (6)0.0081 (5)0.0066 (5)0.0075 (5)
N20.0228 (6)0.0309 (7)0.0217 (6)0.0132 (5)0.0079 (5)0.0112 (5)
C10.0214 (7)0.0221 (7)0.0293 (8)0.0075 (5)0.0089 (6)0.0104 (6)
C20.0246 (8)0.0301 (8)0.0381 (9)0.0092 (6)0.0062 (7)0.0166 (7)
C30.0222 (8)0.0323 (8)0.0563 (12)0.0104 (7)0.0107 (8)0.0239 (8)
C40.0278 (8)0.0303 (8)0.0588 (12)0.0144 (7)0.0246 (8)0.0240 (8)
C50.0290 (8)0.0259 (7)0.0379 (9)0.0102 (6)0.0182 (7)0.0136 (7)
C60.0215 (7)0.0198 (6)0.0310 (8)0.0056 (5)0.0105 (6)0.0094 (6)
C70.0211 (7)0.0229 (7)0.0237 (7)0.0047 (5)0.0073 (6)0.0050 (6)
C80.0208 (7)0.0268 (7)0.0237 (8)0.0063 (6)0.0070 (6)0.0076 (6)
C90.0226 (7)0.0239 (7)0.0368 (9)0.0076 (6)0.0074 (6)0.0109 (6)
C100.0236 (7)0.0205 (7)0.0272 (8)0.0060 (6)0.0058 (6)0.0088 (6)
C110.0287 (8)0.0303 (8)0.0325 (9)0.0071 (6)0.0133 (7)0.0148 (7)
C120.0360 (9)0.0315 (8)0.0309 (9)0.0082 (7)0.0050 (7)0.0180 (7)
C130.0249 (8)0.0239 (7)0.0367 (9)0.0096 (6)0.0013 (7)0.0115 (6)
C140.0253 (7)0.0252 (7)0.0318 (9)0.0089 (6)0.0104 (6)0.0100 (6)
C150.0273 (8)0.0247 (7)0.0255 (8)0.0100 (6)0.0079 (6)0.0115 (6)
C160.0232 (7)0.0315 (8)0.0257 (8)0.0049 (6)0.0068 (6)0.0085 (6)
C170.0278 (8)0.0293 (8)0.0235 (8)0.0048 (6)0.0073 (6)0.0091 (6)
C180.0208 (7)0.0274 (7)0.0230 (7)0.0107 (6)0.0068 (6)0.0105 (6)
C190.0292 (8)0.0383 (9)0.0268 (8)0.0171 (7)0.0073 (6)0.0153 (7)
C200.0257 (8)0.0353 (8)0.0329 (9)0.0160 (7)0.0028 (7)0.0117 (7)
C210.0200 (7)0.0288 (8)0.0360 (9)0.0102 (6)0.0077 (6)0.0073 (7)
C220.0247 (7)0.0261 (7)0.0307 (8)0.0099 (6)0.0119 (6)0.0107 (6)
C230.0191 (7)0.0207 (6)0.0205 (7)0.0062 (5)0.0048 (5)0.0071 (5)
C240.0205 (7)0.0223 (7)0.0197 (7)0.0065 (5)0.0060 (5)0.0063 (5)
C250.0209 (7)0.0293 (7)0.0214 (7)0.0105 (6)0.0059 (6)0.0117 (6)
C260.0208 (7)0.0298 (8)0.0302 (8)0.0085 (6)0.0042 (6)0.0065 (6)
C270.0213 (7)0.0260 (7)0.0234 (8)0.0086 (6)0.0063 (6)0.0050 (6)
C280.0273 (8)0.0301 (8)0.0313 (9)0.0090 (6)0.0135 (7)0.0101 (6)
C290.0439 (10)0.0333 (9)0.0340 (9)0.0171 (8)0.0124 (8)0.0162 (7)
C300.0331 (9)0.0328 (8)0.0307 (9)0.0194 (7)0.0021 (7)0.0075 (7)
C310.0196 (7)0.0283 (8)0.0293 (8)0.0093 (6)0.0075 (6)0.0019 (6)
C320.0244 (7)0.0254 (7)0.0260 (8)0.0084 (6)0.0086 (6)0.0077 (6)
C330.0240 (7)0.0288 (7)0.0228 (7)0.0089 (6)0.0080 (6)0.0106 (6)
C340.0282 (8)0.0263 (7)0.0219 (7)0.0067 (6)0.0080 (6)0.0102 (6)
Geometric parameters (Å, º) top
S1—O21.4282 (12)C9—H9A0.9900
S1—O11.4347 (12)C9—H9B0.9900
S1—N11.6365 (13)C10—C111.380 (2)
S1—C11.7708 (16)C10—C151.396 (2)
S2—O61.4298 (13)C11—C121.384 (2)
S2—O51.4342 (13)C12—C131.369 (2)
S2—N21.6322 (13)C12—H120.9500
S2—C181.7603 (15)C13—C141.374 (2)
F1—C111.3553 (18)C14—C151.376 (2)
F2—C131.3525 (18)C15—H150.9500
F3—C141.3494 (18)C16—C171.478 (2)
F4—C281.3578 (18)C16—H160.9500
F5—C301.3519 (19)C18—C191.388 (2)
F6—C311.3554 (17)C18—C231.415 (2)
O4—C171.2156 (19)C19—C201.383 (2)
O3—C171.326 (2)C19—H190.9500
O3—H3O0.85 (3)C20—C211.375 (2)
O7—C341.3189 (19)C20—H200.9500
O7—H7O0.92 (3)C21—C221.389 (2)
O8—C341.2224 (19)C21—H210.9500
N1—C81.4841 (19)C22—C231.401 (2)
N1—C91.4853 (19)C22—H220.9500
N2—C251.4725 (19)C23—C241.485 (2)
N2—C261.480 (2)C24—C331.351 (2)
C1—C21.392 (2)C24—C251.521 (2)
C1—C61.407 (2)C25—H25A0.9900
C2—C31.388 (2)C25—H25B0.9900
C2—H20.9500C26—C271.508 (2)
C3—C41.383 (3)C26—H26A0.9900
C3—H30.9500C26—H26B0.9900
C4—C51.385 (2)C27—C281.379 (2)
C4—H40.9500C27—C321.397 (2)
C5—C61.401 (2)C28—C291.383 (2)
C5—H50.9500C29—C301.373 (2)
C6—C71.487 (2)C29—H290.9500
C7—C161.343 (2)C30—C311.374 (2)
C7—C81.516 (2)C31—C321.372 (2)
C8—H8A0.9900C32—H320.9500
C8—H8B0.9900C33—C341.475 (2)
C9—C101.510 (2)C33—H330.9500
O2—S1—O1118.55 (7)C13—C14—C15120.66 (15)
O2—S1—N1108.96 (7)C14—C15—C10120.07 (14)
O1—S1—N1107.34 (7)C14—C15—H15120.0
O2—S1—C1110.39 (7)C10—C15—H15120.0
O1—S1—C1106.24 (7)C7—C16—C17128.74 (15)
N1—S1—C1104.43 (7)C7—C16—H16115.6
O6—S2—O5118.94 (8)C17—C16—H16115.6
O6—S2—N2108.52 (7)O4—C17—O3122.46 (15)
O5—S2—N2107.54 (7)O4—C17—C16125.63 (15)
O6—S2—C18109.72 (7)O3—C17—C16111.87 (14)
O5—S2—C18107.20 (7)C19—C18—C23122.65 (14)
N2—S2—C18103.89 (7)C19—C18—S2115.21 (12)
C17—O3—H3O111.3 (19)C23—C18—S2122.13 (11)
C34—O7—H7O108.4 (16)C20—C19—C18119.63 (15)
C8—N1—C9115.31 (12)C20—C19—H19120.2
C8—N1—S1111.40 (10)C18—C19—H19120.2
C9—N1—S1117.72 (10)C21—C20—C19119.25 (15)
C25—N2—C26115.52 (12)C21—C20—H20120.4
C25—N2—S2110.86 (10)C19—C20—H20120.4
C26—N2—S2118.25 (10)C20—C21—C22121.26 (15)
C2—C1—C6121.78 (14)C20—C21—H21119.4
C2—C1—S1117.04 (12)C22—C21—H21119.4
C6—C1—S1120.96 (11)C21—C22—C23121.56 (15)
C3—C2—C1119.30 (17)C21—C22—H22119.2
C3—C2—H2120.3C23—C22—H22119.2
C1—C2—H2120.3C22—C23—C18115.61 (14)
C4—C3—C2119.67 (16)C22—C23—C24123.11 (13)
C4—C3—H3120.2C18—C23—C24121.24 (13)
C2—C3—H3120.2C33—C24—C23130.34 (14)
C3—C4—C5120.76 (16)C33—C24—C25114.86 (13)
C3—C4—H4119.6C23—C24—C25114.79 (12)
C5—C4—H4119.6N2—C25—C24112.43 (12)
C4—C5—C6121.02 (16)N2—C25—H25A109.1
C4—C5—H5119.5C24—C25—H25A109.1
C6—C5—H5119.5N2—C25—H25B109.1
C5—C6—C1116.90 (15)C24—C25—H25B109.1
C5—C6—C7122.38 (15)H25A—C25—H25B107.8
C1—C6—C7120.71 (13)N2—C26—C27108.89 (12)
C16—C7—C6127.74 (14)N2—C26—H26A109.9
C16—C7—C8117.96 (14)C27—C26—H26A109.9
C6—C7—C8114.11 (13)N2—C26—H26B109.9
N1—C8—C7109.66 (12)C27—C26—H26B109.9
N1—C8—H8A109.7H26A—C26—H26B108.3
C7—C8—H8A109.7C28—C27—C32117.47 (14)
N1—C8—H8B109.7C28—C27—C26122.76 (14)
C7—C8—H8B109.7C32—C27—C26119.77 (14)
H8A—C8—H8B108.2F4—C28—C27118.67 (14)
N1—C9—C10110.27 (12)F4—C28—C29117.60 (15)
N1—C9—H9A109.6C27—C28—C29123.74 (15)
C10—C9—H9A109.6C30—C29—C28117.02 (16)
N1—C9—H9B109.6C30—C29—H29121.5
C10—C9—H9B109.6C28—C29—H29121.5
H9A—C9—H9B108.1F5—C30—C29120.43 (16)
C11—C10—C15117.22 (14)F5—C30—C31118.55 (16)
C11—C10—C9122.38 (14)C29—C30—C31121.00 (15)
C15—C10—C9120.36 (14)F6—C31—C32119.75 (15)
F1—C11—C10118.92 (15)F6—C31—C30119.01 (14)
F1—C11—C12117.63 (14)C32—C31—C30121.24 (15)
C10—C11—C12123.44 (15)C31—C32—C27119.54 (15)
C13—C12—C11117.47 (15)C31—C32—H32120.2
C13—C12—H12121.3C27—C32—H32120.2
C11—C12—H12121.3C24—C33—C34133.41 (15)
F2—C13—C12119.91 (15)C24—C33—H33113.3
F2—C13—C14118.98 (15)C34—C33—H33113.3
C12—C13—C14121.11 (15)O8—C34—O7121.92 (14)
F3—C14—C13118.81 (14)O8—C34—C33127.55 (14)
F3—C14—C15120.53 (14)O7—C34—C33110.48 (14)
O2—S1—N1—C8165.08 (10)C11—C10—C15—C140.3 (2)
O1—S1—N1—C8−65.38 (11)C9—C10—C15—C14178.24 (14)
C1—S1—N1—C847.13 (11)C6—C7—C16—C17−4.9 (3)
O2—S1—N1—C928.63 (13)C8—C7—C16—C17169.70 (15)
O1—S1—N1—C9158.17 (11)C7—C16—C17—O4−7.5 (3)
C1—S1—N1—C9−89.32 (12)C7—C16—C17—O3174.59 (16)
O6—S2—N2—C25−164.94 (10)O6—S2—C18—C19−49.22 (15)
O5—S2—N2—C2565.20 (11)O5—S2—C18—C1981.24 (13)
C18—S2—N2—C25−48.23 (11)N2—S2—C18—C19−165.08 (12)
O6—S2—N2—C26−28.22 (13)O6—S2—C18—C23132.05 (13)
O5—S2—N2—C26−158.09 (11)O5—S2—C18—C23−97.48 (13)
C18—S2—N2—C2688.48 (12)N2—S2—C18—C2316.19 (14)
O2—S1—C1—C248.83 (14)C23—C18—C19—C200.8 (2)
O1—S1—C1—C2−80.91 (13)S2—C18—C19—C20−177.93 (13)
N1—S1—C1—C2165.80 (12)C18—C19—C20—C210.6 (3)
O2—S1—C1—C6−136.40 (12)C19—C20—C21—C22−0.6 (2)
O1—S1—C1—C693.86 (13)C20—C21—C22—C23−1.0 (2)
N1—S1—C1—C6−19.43 (14)C21—C22—C23—C182.3 (2)
C6—C1—C2—C3−4.0 (2)C21—C22—C23—C24180.00 (14)
S1—C1—C2—C3170.69 (12)C19—C18—C23—C22−2.2 (2)
C1—C2—C3—C4−2.9 (2)S2—C18—C23—C22176.43 (11)
C2—C3—C4—C55.6 (2)C19—C18—C23—C24−179.98 (14)
C3—C4—C5—C6−1.4 (2)S2—C18—C23—C24−1.3 (2)
C4—C5—C6—C1−5.3 (2)C22—C23—C24—C3318.1 (2)
C4—C5—C6—C7175.82 (14)C18—C23—C24—C33−164.34 (16)
C2—C1—C6—C58.0 (2)C22—C23—C24—C25−160.80 (13)
S1—C1—C6—C5−166.50 (11)C18—C23—C24—C2516.81 (19)
C2—C1—C6—C7−173.07 (14)C26—N2—C25—C24−67.74 (16)
S1—C1—C6—C712.41 (19)S2—N2—C25—C2470.24 (14)
C5—C6—C7—C16−37.3 (2)C33—C24—C25—N2128.86 (14)
C1—C6—C7—C16143.83 (16)C23—C24—C25—N2−52.10 (17)
C5—C6—C7—C8147.93 (14)C25—N2—C26—C27−77.84 (15)
C1—C6—C7—C8−30.93 (19)S2—N2—C26—C27147.39 (11)
C9—N1—C8—C767.11 (16)N2—C26—C27—C28117.32 (16)
S1—N1—C8—C7−70.46 (14)N2—C26—C27—C32−61.75 (19)
C16—C7—C8—N1−115.16 (15)C32—C27—C28—F4179.40 (14)
C6—C7—C8—N160.14 (16)C26—C27—C28—F40.3 (2)
C8—N1—C9—C1076.81 (16)C32—C27—C28—C29−0.7 (2)
S1—N1—C9—C10−148.39 (11)C26—C27—C28—C29−179.81 (16)
N1—C9—C10—C11−124.09 (16)F4—C28—C29—C30−179.77 (15)
N1—C9—C10—C1558.04 (19)C27—C28—C29—C300.3 (3)
C15—C10—C11—F1178.93 (14)C28—C29—C30—F5178.65 (15)
C9—C10—C11—F11.0 (2)C28—C29—C30—C310.1 (3)
C15—C10—C11—C12−0.6 (2)F5—C30—C31—F60.6 (2)
C9—C10—C11—C12−178.53 (15)C29—C30—C31—F6179.15 (15)
F1—C11—C12—C13−179.90 (15)F5—C30—C31—C32−178.77 (14)
C10—C11—C12—C13−0.4 (3)C29—C30—C31—C32−0.2 (3)
C11—C12—C13—F2−178.60 (14)F6—C31—C32—C27−179.54 (13)
C11—C12—C13—C141.7 (2)C30—C31—C32—C27−0.2 (2)
F2—C13—C14—F3−2.4 (2)C28—C27—C32—C310.6 (2)
C12—C13—C14—F3177.31 (15)C26—C27—C32—C31179.73 (14)
F2—C13—C14—C15178.23 (14)C23—C24—C33—C341.9 (3)
C12—C13—C14—C15−2.1 (2)C25—C24—C33—C34−179.25 (15)
F3—C14—C15—C10−178.34 (14)C24—C33—C34—O814.6 (3)
C13—C14—C15—C101.0 (2)C24—C33—C34—O7−168.18 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O8i0.85 (3)1.86 (3)2.7063 (17)172 (3)
O7—H7O···O4ii0.92 (3)1.73 (3)2.6473 (17)177 (2)
C15—H15···O60.952.343.267 (2)165
C32—H32···O20.952.613.539 (2)165
Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O8i0.85 (3)1.86 (3)2.7063 (17)172 (3)
O7—H7O···O4ii0.92 (3)1.73 (3)2.6473 (17)177 (2)
C15—H15···O60.952.343.267 (2)165
C32—H32···O20.952.613.539 (2)165
Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21272025), the Research Fund for the Doctoral Program of Higher Education of China (grant No. 20111101110042) and the Science and Technology Commission of Beijing (China) (grant No. Z131100004013003).

References

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o775
https://doi.org/10.1107/S1600536814013245
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