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Acta Crystallogr Sect E Struct Rep Online. 2011 August 1; 67(Pt 8): o1913–o1914.
Published online 2011 July 6. doi:  10.1107/S1600536811025141
PMCID: PMC3212305

Methyl (2Z)-2-(2-fluoro-4-meth­oxy­benzyl­idene)-5-(4-meth­oxy­phen­yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C24H21FN2O5S, consists of two crystallographically independent mol­ecules. In each mol­ecule, the central dihydro­pyrimidine ring is significantly puckered and adopts a conformation which is best described as an inter­mediate between a boat and a screw boat. The least-squares planes of the dihydro­pyrimidine rings are almost coplanar with the fluoro-substituted benzene rings, making dihedral angles of 9.04 (7) and 6.68 (7)°, and almost perpendicular to the meth­oxy-substituted benzene rings with dihedral angles of 89.23 (7) and 88.30 (7)°. In the mol­ecular structure, S(6) ring motifs are formed by C—H(...)O and C—H(...)S hydrogen bonds. In the crystal, mol­ecules are linked into a three-dimensional network by inter­molecular C—H(...)O and C—H(...)F hydrogen bonds. The crystal structure is further stabilized by a C—H(...)π inter­action.

Related literature

For background to pyrimidine and its derivatives, see: Brugnatelli (1818 [triangle]); Smee et al. (1987 [triangle]); Lagu et al. (2000 [triangle]). For background to thia­zole and its derivatives, see: Holla et al. (2003 [triangle]); Narayana et al. (2004 [triangle]); Sarojini et al. (2010 [triangle]). For the effect of fluorine in a mol­ecule on its biological activity, see: Filler & Kobayashi (1982 [triangle]). For related structures, see: Fischer et al. (2007 [triangle]); Jotani et al. (2010 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]). For puckering parameters, see: Cremer & Pople (1975) [triangle].

An external file that holds a picture, illustration, etc.
Object name is e-67-o1913-scheme1.jpg

Experimental

Crystal data

  • C24H21FN2O5S
  • M r = 468.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-o1913-efi1.jpg
  • a = 11.7374 (2) Å
  • b = 14.3062 (2) Å
  • c = 14.5552 (2) Å
  • α = 61.939 (1)°
  • β = 80.791 (1)°
  • γ = 84.878 (1)°
  • V = 2128.69 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 100 K
  • 0.37 × 0.33 × 0.10 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.929, T max = 0.980
  • 46547 measured reflections
  • 12629 independent reflections
  • 10022 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.123
  • S = 1.04
  • 12629 reflections
  • 602 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025141/is2738sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025141/is2738Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025141/is2738Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. KU thanks P. A. College of Engin­eering for the research facilities.

supplementary crystallographic information

Comment

Pyrimidine derivatives are known for their varied biological properties. Brugnatelli was the first scientist to isolate 'Alloxan', a pyrimidine derivative in 1818, and later this compound was found to possess antineoplastic properties (Brugnatelli, 1818). Nucleosides of pyrimidine bases have been used extensively as antiviral and anticancer agents (Smee et al., 1987). Recently, fluoropyrimidines and flurouracil-based combination therapy is used in the treatment of gastrointestinal cancer and solid tumors. Furopyrimidinones are found to be metabolites of dihydropyrimidinones that are subtype-selective antagonists of the α1a-adreginic receptor antagonists (Lagu et al., 2000). Thiazoles and their derivatives are found to be associated with various biological activities such as antibacterial, antifungal and anti-inflammatory activities (Holla et al., 2003; Narayana et al., 2004; Sarojini et al., 2010). Presence of fluorine in a molecule enhances drug persistence and lipid solubility (Filler & Kobayashi, 1982). The crystal structure of ethyl 7-methyl-2-[4-(methylsulfanyl)benzylidene] -5-[4-(methylsulfanyl)phenyl]-3-oxo-2,3-dihydro-5H-thiazolo [3,2-a] pyrimidine-6-carboxylate synthesized in an one pot reaction using tin(II) chloride was reported (Fischer et al., 2007). In continuation to our studies on crystal structure of new heterocyclic analogs, we report the synthesis and crystal structure of a new methyl (2Z)-2-[(2-fluoro-4-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7- methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6- carboxylate, C24H20N2FO5S.

The title compound (Fig. 1) consists of two crystallographically independent molecules (molecule A & B). The central pyrimidine rings (N1/C1/N2/C2–C4) are significantly puckered and adopt a conformation which is best described as an intermediate between a boat and screw boat with the puckering parameter (Cremer & Pople, 1975), Q = 0.2565 (15) Å, Θ = 112.0 (3)° and [var phi] = 136.5 (4)° in molecule A; Q = 0.2340 (15) Å, Θ = 69.0 (4)° and [var phi] = 317.1 (4)° in molecule B. The mean planes of pyrimidine rings are almost coplanar with the fluoro-substituted phenyl rings (C8–C13) with dihedral angles of 9.04 (7)° in molecule A and 6.68 (7)° in molecule B; and almost perpendicular with the methoxy-substituted phenyl rings (C17–C22) with dihedral angles of 89.23 (7) and 88.30 (7)°, respectively, in molecule A and B. In the molecular structure, S(6) ring motifs (Bernstein et al., 1995) are formed via intramolecular C14A—H14A···O3A, C14B—H14D···O3B, C13A—H13A···S1A and C13B—H13B···S1B hydrogen bonds (Table 1). Bond lengths and angles are within the normal ranges and are comparable to the related structure (Jotani et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked into three-dimensional network by intermolecular C12A—H12A···O1B, C18A—H18A···O3B, C21A—H21A···F1B and C24A—H24C···O3B hydrogen bonds (Table 1). The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the centroids of C17A–C22A ring (Cg1).

Experimental

A mixture of methyl 4-(4-methoxyphenyl)-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2.59 mmol), chloro acetic acid (0.29 g, 3.11 mmol), 2-fluoro-4-methoxy-benzaldehyde (3.11 mmol) and sodium acetate (10 mmol) in 1:1 mixture glacial acetic acid/ acetic anhydride (10 ml) were heated to 130 °C for 3–5 h. After the completion of the reaction, the reaction mass was cooled to room temperature and quenched to ice cooled water. The solid precipitated out were collected by filtration and recrystallized from acetonitrile/water to afford title compound (m.p. 477.9–478.5 K). Analysis, found (calculated): C 61.50 (61.53), H 4.45 (4.48), N 5.97% (5.98%).

Refinement

All H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C) (C—H = 0.95–1.00 °). A rotating group model was applied to the methyl groups. There is no pseudo-symmetry in the crystal structure.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates the intramolecular hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C24H21FN2O5SZ = 4
Mr = 468.49F(000) = 976
Triclinic, P1Dx = 1.462 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.7374 (2) ÅCell parameters from 9870 reflections
b = 14.3062 (2) Åθ = 2.5–30.2°
c = 14.5552 (2) ŵ = 0.20 mm1
α = 61.939 (1)°T = 100 K
β = 80.791 (1)°Plate, yellow
γ = 84.878 (1)°0.37 × 0.33 × 0.10 mm
V = 2128.69 (6) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer12629 independent reflections
Radiation source: fine-focus sealed tube10022 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 30.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→16
Tmin = 0.929, Tmax = 0.980k = −19→20
46547 measured reflectionsl = −20→20

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0608P)2 + 0.8664P] where P = (Fo2 + 2Fc2)/3
12629 reflections(Δ/σ)max = 0.001
602 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.49 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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)

xyzUiso*/Ueq
S1A0.74753 (3)0.78373 (3)0.38302 (3)0.01691 (8)
F1A1.06880 (7)0.51889 (7)0.31316 (7)0.02532 (19)
O1A0.97502 (9)0.88905 (8)0.13570 (8)0.0236 (2)
O2A0.86743 (9)1.26518 (8)0.02597 (8)0.0226 (2)
O3A0.70722 (10)1.31812 (9)0.09628 (9)0.0289 (2)
O4A1.26523 (9)1.11070 (9)0.31666 (8)0.0220 (2)
O5A0.83717 (9)0.25364 (8)0.60271 (8)0.0228 (2)
N1A0.83373 (10)0.95336 (9)0.22110 (9)0.0154 (2)
N2A0.67609 (10)0.98277 (10)0.32890 (9)0.0182 (2)
C1A0.74917 (12)0.92232 (11)0.30607 (10)0.0160 (2)
C2A0.67868 (12)1.09231 (11)0.25526 (11)0.0171 (3)
C3A0.76554 (12)1.13335 (11)0.17452 (11)0.0163 (3)
C4A0.86866 (11)1.06546 (10)0.16296 (10)0.0152 (2)
H4AA0.89021.08490.08690.018*
C5A0.89772 (12)0.87326 (11)0.20725 (11)0.0169 (3)
C6A0.85833 (12)0.76833 (11)0.29416 (10)0.0165 (3)
C7A0.91184 (12)0.67857 (11)0.29940 (11)0.0171 (3)
H7AA0.97240.68830.24410.021*
C8A0.88975 (12)0.56950 (11)0.37761 (10)0.0164 (3)
C9A0.97110 (12)0.49082 (11)0.38290 (11)0.0175 (3)
C10A0.95972 (12)0.38516 (11)0.45515 (11)0.0183 (3)
H10A1.01850.33480.45580.022*
C11A0.85951 (12)0.35454 (11)0.52711 (11)0.0177 (3)
C12A0.77288 (12)0.43003 (11)0.52394 (11)0.0182 (3)
H12A0.70360.40900.57190.022*
C13A0.78905 (12)0.53461 (11)0.45091 (11)0.0173 (3)
H13A0.73020.58510.44990.021*
C14A0.57542 (12)1.15044 (12)0.27907 (12)0.0227 (3)
H14A0.58191.22620.22990.034*
H14B0.57131.13990.35110.034*
H14C0.50541.12330.27180.034*
C15A0.77248 (12)1.24770 (11)0.09754 (11)0.0179 (3)
C16A0.88851 (16)1.37461 (12)−0.04928 (13)0.0290 (3)
H16A0.95941.3794−0.09700.044*
H16B0.89711.4152−0.01220.044*
H16C0.82341.4036−0.08970.044*
C17A0.97262 (11)1.08027 (10)0.20475 (10)0.0146 (2)
C18A0.96020 (12)1.08372 (11)0.29973 (11)0.0168 (3)
H18A0.88531.07900.33770.020*
C19A1.05591 (12)1.09396 (11)0.34035 (11)0.0177 (3)
H19A1.04621.09590.40550.021*
C20A1.16530 (12)1.10132 (11)0.28444 (11)0.0173 (3)
C21A1.17872 (12)1.09913 (12)0.18825 (11)0.0198 (3)
H21A1.25341.10470.14980.024*
C22A1.08299 (12)1.08886 (11)0.14903 (11)0.0181 (3)
H22A1.09261.08770.08350.022*
C23A1.25509 (14)1.10826 (15)0.41683 (13)0.0281 (3)
H23A1.33181.11430.43180.042*
H23B1.22071.04130.47120.042*
H23C1.20581.16750.41620.042*
C24A0.91703 (14)0.17216 (12)0.60228 (12)0.0240 (3)
H24A0.89210.10390.66150.036*
H24B0.99400.18800.60870.036*
H24C0.91960.16870.53630.036*
S1B0.73247 (3)0.73597 (3)0.09732 (3)0.01691 (8)
F1B0.43727 (7)1.00519 (7)0.19386 (7)0.02408 (19)
O1B0.50193 (9)0.63422 (8)0.34200 (8)0.0209 (2)
O2B0.61941 (9)0.25875 (8)0.46823 (8)0.0207 (2)
O3B0.78696 (9)0.20771 (8)0.40519 (8)0.0236 (2)
O4B0.21975 (9)0.37224 (9)0.19460 (8)0.0222 (2)
O5B0.63291 (10)1.27590 (8)−0.10488 (8)0.0250 (2)
N1B0.64551 (10)0.56854 (9)0.26041 (9)0.0151 (2)
N2B0.81022 (10)0.53686 (9)0.16058 (9)0.0173 (2)
C1B0.73321 (11)0.59824 (11)0.17804 (10)0.0157 (2)
C2B0.80789 (11)0.42898 (11)0.23771 (10)0.0160 (2)
C3B0.71905 (11)0.38889 (11)0.31656 (10)0.0151 (2)
C4B0.61373 (11)0.45619 (10)0.32381 (10)0.0147 (2)
H4BA0.59240.44110.39870.018*
C5B0.57923 (11)0.64961 (11)0.27055 (10)0.0160 (2)
C6B0.61960 (11)0.75356 (11)0.18334 (10)0.0161 (2)
C7B0.56982 (12)0.84384 (11)0.17922 (10)0.0164 (3)
H7BA0.50930.83430.23450.020*
C8B0.59422 (12)0.95327 (11)0.10361 (10)0.0162 (3)
C9B0.52370 (12)1.03373 (11)0.11276 (11)0.0176 (3)
C10B0.53657 (12)1.13969 (11)0.04417 (11)0.0194 (3)
H10B0.48591.19100.05350.023*
C11B0.62607 (13)1.17023 (11)−0.03983 (11)0.0189 (3)
C12B0.70110 (13)1.09380 (12)−0.05141 (11)0.0214 (3)
H12B0.76301.1142−0.10740.026*
C13B0.68413 (13)0.98811 (12)0.01961 (11)0.0202 (3)
H13B0.73570.93680.01110.024*
C14B0.91448 (12)0.37015 (12)0.22093 (12)0.0206 (3)
H14D0.90230.29380.26330.031*
H14E0.97960.39040.24200.031*
H14F0.93140.38780.14650.031*
C15B0.71571 (12)0.27668 (11)0.39846 (10)0.0166 (3)
C16B0.60587 (14)0.15225 (12)0.55346 (12)0.0261 (3)
H16D0.52950.14580.59440.039*
H16E0.66560.13690.59890.039*
H16F0.61340.10190.52490.039*
C17B0.51005 (11)0.43441 (10)0.28660 (10)0.0150 (2)
C18B0.51751 (12)0.44252 (12)0.18702 (11)0.0193 (3)
H18B0.58860.46180.14150.023*
C19B0.42220 (12)0.42283 (12)0.15258 (11)0.0202 (3)
H19B0.42820.42920.08400.024*
C20B0.31845 (12)0.39380 (11)0.21960 (11)0.0173 (3)
C21B0.31040 (12)0.38513 (12)0.32011 (11)0.0204 (3)
H21B0.23960.36550.36590.025*
C22B0.40572 (12)0.40517 (12)0.35291 (11)0.0187 (3)
H22B0.39980.39890.42140.022*
C23B0.22887 (14)0.37021 (14)0.09641 (13)0.0274 (3)
H23D0.15440.35090.08830.041*
H23E0.28800.31790.09470.041*
H23F0.25050.44040.03890.041*
C24B0.71782 (15)1.30983 (13)−0.19621 (12)0.0299 (3)
H24D0.71141.3868−0.23900.045*
H24E0.70511.2748−0.23750.045*
H24F0.79501.2912−0.17460.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.01787 (16)0.01556 (16)0.01531 (15)−0.00280 (12)0.00011 (12)−0.00582 (12)
F1A0.0188 (4)0.0223 (4)0.0273 (5)−0.0011 (3)0.0040 (3)−0.0074 (4)
O1A0.0270 (5)0.0179 (5)0.0206 (5)−0.0025 (4)0.0056 (4)−0.0069 (4)
O2A0.0240 (5)0.0152 (5)0.0208 (5)−0.0008 (4)0.0003 (4)−0.0029 (4)
O3A0.0318 (6)0.0199 (5)0.0287 (6)0.0079 (5)−0.0022 (5)−0.0080 (5)
O4A0.0152 (5)0.0293 (6)0.0234 (5)−0.0021 (4)−0.0046 (4)−0.0130 (5)
O5A0.0272 (5)0.0144 (5)0.0213 (5)−0.0013 (4)−0.0024 (4)−0.0039 (4)
N1A0.0160 (5)0.0137 (5)0.0146 (5)−0.0019 (4)−0.0014 (4)−0.0050 (4)
N2A0.0163 (5)0.0179 (6)0.0197 (6)−0.0016 (4)−0.0016 (4)−0.0082 (5)
C1A0.0153 (6)0.0177 (6)0.0145 (6)−0.0031 (5)−0.0027 (5)−0.0064 (5)
C2A0.0146 (6)0.0185 (6)0.0197 (6)0.0003 (5)−0.0040 (5)−0.0096 (5)
C3A0.0150 (6)0.0149 (6)0.0181 (6)0.0010 (5)−0.0048 (5)−0.0064 (5)
C4A0.0153 (6)0.0141 (6)0.0153 (6)−0.0012 (5)−0.0028 (5)−0.0057 (5)
C5A0.0187 (6)0.0152 (6)0.0166 (6)−0.0017 (5)−0.0022 (5)−0.0069 (5)
C6A0.0177 (6)0.0169 (6)0.0141 (6)−0.0036 (5)−0.0020 (5)−0.0059 (5)
C7A0.0177 (6)0.0180 (6)0.0156 (6)−0.0032 (5)−0.0015 (5)−0.0076 (5)
C8A0.0180 (6)0.0156 (6)0.0162 (6)−0.0021 (5)−0.0031 (5)−0.0074 (5)
C9A0.0157 (6)0.0192 (7)0.0165 (6)−0.0024 (5)−0.0013 (5)−0.0074 (5)
C10A0.0178 (6)0.0173 (7)0.0199 (6)0.0008 (5)−0.0050 (5)−0.0081 (5)
C11A0.0221 (7)0.0153 (6)0.0156 (6)−0.0022 (5)−0.0054 (5)−0.0059 (5)
C12A0.0188 (6)0.0185 (7)0.0159 (6)−0.0033 (5)−0.0001 (5)−0.0071 (5)
C13A0.0184 (6)0.0160 (6)0.0185 (6)0.0002 (5)−0.0029 (5)−0.0089 (5)
C14A0.0172 (7)0.0217 (7)0.0290 (7)0.0012 (5)−0.0004 (6)−0.0126 (6)
C15A0.0191 (6)0.0181 (6)0.0170 (6)−0.0003 (5)−0.0060 (5)−0.0072 (5)
C16A0.0381 (9)0.0171 (7)0.0230 (7)−0.0027 (6)−0.0011 (7)−0.0026 (6)
C17A0.0137 (6)0.0119 (6)0.0159 (6)0.0000 (5)−0.0023 (5)−0.0044 (5)
C18A0.0139 (6)0.0182 (6)0.0187 (6)−0.0001 (5)−0.0003 (5)−0.0093 (5)
C19A0.0178 (6)0.0185 (6)0.0184 (6)0.0003 (5)−0.0027 (5)−0.0099 (5)
C20A0.0152 (6)0.0156 (6)0.0198 (6)−0.0002 (5)−0.0046 (5)−0.0064 (5)
C21A0.0144 (6)0.0227 (7)0.0196 (6)−0.0012 (5)−0.0004 (5)−0.0080 (6)
C22A0.0167 (6)0.0200 (7)0.0155 (6)−0.0008 (5)−0.0004 (5)−0.0069 (5)
C23A0.0233 (7)0.0404 (9)0.0285 (8)−0.0028 (7)−0.0067 (6)−0.0211 (7)
C24A0.0280 (8)0.0154 (7)0.0258 (7)0.0013 (6)−0.0098 (6)−0.0056 (6)
S1B0.01764 (16)0.01579 (16)0.01431 (15)−0.00132 (12)0.00060 (12)−0.00518 (12)
F1B0.0216 (4)0.0228 (5)0.0226 (4)0.0024 (3)0.0026 (3)−0.0085 (4)
O1B0.0198 (5)0.0194 (5)0.0198 (5)−0.0009 (4)0.0035 (4)−0.0079 (4)
O2B0.0187 (5)0.0172 (5)0.0186 (5)0.0001 (4)−0.0003 (4)−0.0027 (4)
O3B0.0252 (5)0.0203 (5)0.0223 (5)0.0070 (4)−0.0052 (4)−0.0080 (4)
O4B0.0151 (5)0.0271 (6)0.0270 (5)−0.0020 (4)−0.0050 (4)−0.0139 (5)
O5B0.0336 (6)0.0162 (5)0.0198 (5)−0.0040 (4)−0.0040 (4)−0.0033 (4)
N1B0.0144 (5)0.0144 (5)0.0146 (5)−0.0011 (4)−0.0009 (4)−0.0054 (4)
N2B0.0156 (5)0.0175 (6)0.0162 (5)−0.0001 (4)−0.0004 (4)−0.0064 (5)
C1B0.0144 (6)0.0184 (6)0.0140 (6)−0.0021 (5)−0.0018 (5)−0.0070 (5)
C2B0.0143 (6)0.0174 (6)0.0174 (6)0.0004 (5)−0.0037 (5)−0.0088 (5)
C3B0.0140 (6)0.0158 (6)0.0157 (6)0.0013 (5)−0.0039 (5)−0.0071 (5)
C4B0.0135 (6)0.0141 (6)0.0140 (6)−0.0008 (5)−0.0008 (5)−0.0047 (5)
C5B0.0153 (6)0.0165 (6)0.0162 (6)−0.0005 (5)−0.0031 (5)−0.0073 (5)
C6B0.0153 (6)0.0173 (6)0.0142 (6)−0.0019 (5)−0.0018 (5)−0.0059 (5)
C7B0.0153 (6)0.0181 (6)0.0152 (6)−0.0014 (5)−0.0019 (5)−0.0071 (5)
C8B0.0172 (6)0.0162 (6)0.0160 (6)0.0000 (5)−0.0047 (5)−0.0073 (5)
C9B0.0171 (6)0.0205 (7)0.0150 (6)−0.0013 (5)−0.0028 (5)−0.0076 (5)
C10B0.0211 (7)0.0186 (7)0.0200 (6)0.0019 (5)−0.0068 (5)−0.0093 (5)
C11B0.0241 (7)0.0151 (6)0.0171 (6)−0.0031 (5)−0.0066 (5)−0.0056 (5)
C12B0.0236 (7)0.0208 (7)0.0176 (6)−0.0046 (6)0.0006 (5)−0.0074 (6)
C13B0.0219 (7)0.0185 (7)0.0198 (6)−0.0012 (5)−0.0008 (5)−0.0090 (6)
C14B0.0166 (6)0.0204 (7)0.0238 (7)0.0016 (5)0.0002 (5)−0.0105 (6)
C15B0.0173 (6)0.0182 (6)0.0152 (6)−0.0001 (5)−0.0044 (5)−0.0078 (5)
C16B0.0261 (8)0.0194 (7)0.0212 (7)−0.0025 (6)−0.0013 (6)−0.0002 (6)
C17B0.0135 (6)0.0137 (6)0.0155 (6)0.0006 (5)−0.0024 (5)−0.0050 (5)
C18B0.0151 (6)0.0240 (7)0.0176 (6)−0.0035 (5)0.0002 (5)−0.0088 (6)
C19B0.0187 (7)0.0244 (7)0.0181 (6)−0.0013 (5)−0.0034 (5)−0.0098 (6)
C20B0.0144 (6)0.0149 (6)0.0222 (6)0.0007 (5)−0.0050 (5)−0.0078 (5)
C21B0.0146 (6)0.0233 (7)0.0216 (7)−0.0025 (5)0.0003 (5)−0.0094 (6)
C22B0.0161 (6)0.0216 (7)0.0165 (6)−0.0011 (5)0.0000 (5)−0.0079 (5)
C23B0.0211 (7)0.0368 (9)0.0344 (8)−0.0011 (6)−0.0071 (6)−0.0238 (8)
C24B0.0373 (9)0.0222 (8)0.0219 (7)−0.0080 (7)−0.0019 (7)−0.0028 (6)

Geometric parameters (Å, °)

S1A—C6A1.7581 (14)S1B—C1B1.7565 (14)
S1A—C1A1.7597 (14)S1B—C6B1.7585 (14)
F1A—C9A1.3538 (15)F1B—C9B1.3515 (16)
O1A—C5A1.2131 (17)O1B—C5B1.2131 (16)
O2A—C15A1.3501 (17)O2B—C15B1.3469 (16)
O2A—C16A1.4425 (18)O2B—C16B1.4449 (17)
O3A—C15A1.2048 (18)O3B—C15B1.2126 (17)
O4A—C20A1.3700 (16)O4B—C20B1.3689 (16)
O4A—C23A1.4277 (18)O4B—C23B1.4297 (18)
O5A—C11A1.3580 (16)O5B—C11B1.3560 (17)
O5A—C24A1.4308 (18)O5B—C24B1.4322 (19)
N1A—C1A1.3715 (17)N1B—C1B1.3715 (17)
N1A—C5A1.3903 (18)N1B—C5B1.3912 (17)
N1A—C4A1.4784 (17)N1B—C4B1.4749 (17)
N2A—C1A1.2809 (18)N2B—C1B1.2836 (18)
N2A—C2A1.4224 (18)N2B—C2B1.4180 (17)
C2A—C3A1.3563 (19)C2B—C3B1.3557 (18)
C2A—C14A1.4958 (19)C2B—C14B1.4969 (19)
C3A—C15A1.4860 (19)C3B—C15B1.4817 (19)
C3A—C4A1.5216 (19)C3B—C4B1.5191 (18)
C4A—C17A1.5195 (18)C4B—C17B1.5195 (18)
C4A—H4AA1.0000C4B—H4BA1.0000
C5A—C6A1.4892 (19)C5B—C6B1.4848 (19)
C6A—C7A1.352 (2)C6B—C7B1.3479 (19)
C7A—C8A1.4507 (19)C7B—C8B1.4499 (19)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.391 (2)C8B—C13B1.4017 (19)
C8A—C13A1.4089 (19)C8B—C9B1.4023 (19)
C9A—C10A1.3800 (19)C9B—C10B1.3733 (19)
C10A—C11A1.3922 (19)C10B—C11B1.399 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.405 (2)C11B—C12B1.398 (2)
C12A—C13A1.3763 (19)C12B—C13B1.383 (2)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
C16A—H16A0.9800C16B—H16D0.9800
C16A—H16B0.9800C16B—H16E0.9800
C16A—H16C0.9800C16B—H16F0.9800
C17A—C18A1.3905 (18)C17B—C18B1.3874 (18)
C17A—C22A1.3963 (18)C17B—C22B1.3927 (18)
C18A—C19A1.3987 (18)C18B—C19B1.3968 (19)
C18A—H18A0.9500C18B—H18B0.9500
C19A—C20A1.3895 (19)C19B—C20B1.3914 (19)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.3985 (19)C20B—C21B1.3970 (19)
C21A—C22A1.3870 (19)C21B—C22B1.3853 (19)
C21A—H21A0.9500C21B—H21B0.9500
C22A—H22A0.9500C22B—H22B0.9500
C23A—H23A0.9800C23B—H23D0.9800
C23A—H23B0.9800C23B—H23E0.9800
C23A—H23C0.9800C23B—H23F0.9800
C24A—H24A0.9800C24B—H24D0.9800
C24A—H24B0.9800C24B—H24E0.9800
C24A—H24C0.9800C24B—H24F0.9800
C6A—S1A—C1A91.13 (6)C1B—S1B—C6B91.33 (6)
C15A—O2A—C16A115.45 (12)C15B—O2B—C16B116.22 (11)
C20A—O4A—C23A116.84 (11)C20B—O4B—C23B116.59 (11)
C11A—O5A—C24A117.68 (12)C11B—O5B—C24B116.97 (12)
C1A—N1A—C5A116.74 (11)C1B—N1B—C5B116.75 (11)
C1A—N1A—C4A119.51 (11)C1B—N1B—C4B120.30 (11)
C5A—N1A—C4A122.50 (11)C5B—N1B—C4B122.30 (11)
C1A—N2A—C2A116.50 (12)C1B—N2B—C2B116.32 (12)
N2A—C1A—N1A126.57 (13)N2B—C1B—N1B126.41 (13)
N2A—C1A—S1A121.71 (11)N2B—C1B—S1B122.14 (10)
N1A—C1A—S1A111.69 (10)N1B—C1B—S1B111.42 (10)
C3A—C2A—N2A121.64 (12)C3B—C2B—N2B122.00 (12)
C3A—C2A—C14A127.04 (13)C3B—C2B—C14B126.45 (13)
N2A—C2A—C14A111.32 (12)N2B—C2B—C14B111.53 (12)
C2A—C3A—C15A123.13 (13)C2B—C3B—C15B122.75 (12)
C2A—C3A—C4A121.29 (12)C2B—C3B—C4B121.57 (12)
C15A—C3A—C4A115.37 (12)C15B—C3B—C4B115.64 (11)
N1A—C4A—C17A109.69 (10)N1B—C4B—C3B108.06 (10)
N1A—C4A—C3A108.04 (11)N1B—C4B—C17B110.01 (10)
C17A—C4A—C3A112.26 (11)C3B—C4B—C17B113.02 (11)
N1A—C4A—H4AA108.9N1B—C4B—H4BA108.6
C17A—C4A—H4AA108.9C3B—C4B—H4BA108.6
C3A—C4A—H4AA108.9C17B—C4B—H4BA108.6
O1A—C5A—N1A123.89 (13)O1B—C5B—N1B123.30 (13)
O1A—C5A—C6A126.57 (13)O1B—C5B—C6B127.04 (13)
N1A—C5A—C6A109.53 (11)N1B—C5B—C6B109.65 (11)
C7A—C6A—C5A119.98 (12)C7B—C6B—C5B119.92 (12)
C7A—C6A—S1A129.08 (11)C7B—C6B—S1B129.49 (11)
C5A—C6A—S1A110.82 (10)C5B—C6B—S1B110.59 (10)
C6A—C7A—C8A129.12 (13)C6B—C7B—C8B130.12 (13)
C6A—C7A—H7AA115.4C6B—C7B—H7BA114.9
C8A—C7A—H7AA115.4C8B—C7B—H7BA114.9
C9A—C8A—C13A115.48 (12)C13B—C8B—C9B115.22 (13)
C9A—C8A—C7A119.74 (12)C13B—C8B—C7B125.77 (13)
C13A—C8A—C7A124.78 (13)C9B—C8B—C7B119.02 (12)
F1A—C9A—C10A117.14 (12)F1B—C9B—C10B117.93 (12)
F1A—C9A—C8A118.38 (12)F1B—C9B—C8B117.95 (12)
C10A—C9A—C8A124.49 (13)C10B—C9B—C8B124.12 (13)
C9A—C10A—C11A118.03 (13)C9B—C10B—C11B118.45 (13)
C9A—C10A—H10A121.0C9B—C10B—H10B120.8
C11A—C10A—H10A121.0C11B—C10B—H10B120.8
O5A—C11A—C10A124.32 (13)O5B—C11B—C12B124.75 (13)
O5A—C11A—C12A115.59 (12)O5B—C11B—C10B115.22 (13)
C10A—C11A—C12A120.09 (13)C12B—C11B—C10B120.03 (13)
C13A—C12A—C11A119.53 (13)C13B—C12B—C11B119.23 (13)
C13A—C12A—H12A120.2C13B—C12B—H12B120.4
C11A—C12A—H12A120.2C11B—C12B—H12B120.4
C12A—C13A—C8A122.35 (13)C12B—C13B—C8B122.92 (14)
C12A—C13A—H13A118.8C12B—C13B—H13B118.5
C8A—C13A—H13A118.8C8B—C13B—H13B118.5
C2A—C14A—H14A109.5C2B—C14B—H14D109.5
C2A—C14A—H14B109.5C2B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C2A—C14A—H14C109.5C2B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
O3A—C15A—O2A122.37 (13)O3B—C15B—O2B122.50 (13)
O3A—C15A—C3A127.66 (14)O3B—C15B—C3B127.07 (13)
O2A—C15A—C3A109.96 (12)O2B—C15B—C3B110.43 (11)
O2A—C16A—H16A109.5O2B—C16B—H16D109.5
O2A—C16A—H16B109.5O2B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
O2A—C16A—H16C109.5O2B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C18A—C17A—C22A118.73 (12)C18B—C17B—C22B118.95 (12)
C18A—C17A—C4A120.87 (12)C18B—C17B—C4B120.97 (12)
C22A—C17A—C4A120.39 (12)C22B—C17B—C4B120.08 (12)
C17A—C18A—C19A121.20 (12)C17B—C18B—C19B121.05 (13)
C17A—C18A—H18A119.4C17B—C18B—H18B119.5
C19A—C18A—H18A119.4C19B—C18B—H18B119.5
C20A—C19A—C18A119.35 (12)C20B—C19B—C18B119.40 (13)
C20A—C19A—H19A120.3C20B—C19B—H19B120.3
C18A—C19A—H19A120.3C18B—C19B—H19B120.3
O4A—C20A—C19A124.58 (12)O4B—C20B—C19B124.54 (13)
O4A—C20A—C21A115.46 (12)O4B—C20B—C21B115.59 (12)
C19A—C20A—C21A119.96 (12)C19B—C20B—C21B119.87 (12)
C22A—C21A—C20A120.02 (13)C22B—C21B—C20B119.97 (13)
C22A—C21A—H21A120.0C22B—C21B—H21B120.0
C20A—C21A—H21A120.0C20B—C21B—H21B120.0
C21A—C22A—C17A120.72 (13)C21B—C22B—C17B120.76 (13)
C21A—C22A—H22A119.6C21B—C22B—H22B119.6
C17A—C22A—H22A119.6C17B—C22B—H22B119.6
O4A—C23A—H23A109.5O4B—C23B—H23D109.5
O4A—C23A—H23B109.5O4B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
O4A—C23A—H23C109.5O4B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
O5A—C24A—H24A109.5O5B—C24B—H24D109.5
O5A—C24A—H24B109.5O5B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
O5A—C24A—H24C109.5O5B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C2A—N2A—C1A—N1A4.0 (2)C2B—N2B—C1B—N1B−4.0 (2)
C2A—N2A—C1A—S1A−173.94 (9)C2B—N2B—C1B—S1B173.68 (9)
C5A—N1A—C1A—N2A−175.05 (13)C5B—N1B—C1B—N2B173.17 (13)
C4A—N1A—C1A—N2A17.4 (2)C4B—N1B—C1B—N2B−15.8 (2)
C5A—N1A—C1A—S1A3.11 (15)C5B—N1B—C1B—S1B−4.76 (14)
C4A—N1A—C1A—S1A−164.46 (9)C4B—N1B—C1B—S1B166.23 (9)
C6A—S1A—C1A—N2A175.33 (12)C6B—S1B—C1B—N2B−173.17 (12)
C6A—S1A—C1A—N1A−2.93 (10)C6B—S1B—C1B—N1B4.85 (10)
C1A—N2A—C2A—C3A−10.65 (19)C1B—N2B—C2B—C3B10.35 (19)
C1A—N2A—C2A—C14A168.43 (12)C1B—N2B—C2B—C14B−168.29 (12)
N2A—C2A—C3A—C15A−178.59 (12)N2B—C2B—C3B—C15B−179.35 (11)
C14A—C2A—C3A—C15A2.5 (2)C14B—C2B—C3B—C15B−0.9 (2)
N2A—C2A—C3A—C4A−4.1 (2)N2B—C2B—C3B—C4B3.03 (19)
C14A—C2A—C3A—C4A177.00 (13)C14B—C2B—C3B—C4B−178.55 (12)
C1A—N1A—C4A—C17A94.47 (14)C1B—N1B—C4B—C3B25.68 (15)
C5A—N1A—C4A—C17A−72.35 (15)C5B—N1B—C4B—C3B−163.84 (11)
C1A—N1A—C4A—C3A−28.20 (15)C1B—N1B—C4B—C17B−98.13 (13)
C5A—N1A—C4A—C3A164.98 (11)C5B—N1B—C4B—C17B72.35 (15)
C2A—C3A—C4A—N1A22.18 (16)C2B—C3B—C4B—N1B−19.80 (16)
C15A—C3A—C4A—N1A−162.90 (11)C15B—C3B—C4B—N1B162.42 (10)
C2A—C3A—C4A—C17A−98.90 (15)C2B—C3B—C4B—C17B102.17 (14)
C15A—C3A—C4A—C17A76.02 (14)C15B—C3B—C4B—C17B−75.61 (14)
C1A—N1A—C5A—O1A180.00 (13)C1B—N1B—C5B—O1B−177.26 (12)
C4A—N1A—C5A—O1A−12.8 (2)C4B—N1B—C5B—O1B11.9 (2)
C1A—N1A—C5A—C6A−1.46 (16)C1B—N1B—C5B—C6B1.79 (16)
C4A—N1A—C5A—C6A165.70 (11)C4B—N1B—C5B—C6B−169.01 (11)
O1A—C5A—C6A—C7A1.3 (2)O1B—C5B—C6B—C7B1.1 (2)
N1A—C5A—C6A—C7A−177.23 (12)N1B—C5B—C6B—C7B−177.93 (12)
O1A—C5A—C6A—S1A177.66 (12)O1B—C5B—C6B—S1B−179.03 (12)
N1A—C5A—C6A—S1A−0.83 (14)N1B—C5B—C6B—S1B1.97 (13)
C1A—S1A—C6A—C7A178.09 (13)C1B—S1B—C6B—C7B176.05 (13)
C1A—S1A—C6A—C5A2.11 (10)C1B—S1B—C6B—C5B−3.83 (10)
C5A—C6A—C7A—C8A178.41 (12)C5B—C6B—C7B—C8B179.49 (12)
S1A—C6A—C7A—C8A2.7 (2)S1B—C6B—C7B—C8B−0.4 (2)
C6A—C7A—C8A—C9A−164.72 (14)C6B—C7B—C8B—C13B−4.7 (2)
C6A—C7A—C8A—C13A15.9 (2)C6B—C7B—C8B—C9B175.42 (14)
C13A—C8A—C9A—F1A178.69 (11)C13B—C8B—C9B—F1B−178.35 (11)
C7A—C8A—C9A—F1A−0.78 (19)C7B—C8B—C9B—F1B1.54 (18)
C13A—C8A—C9A—C10A−1.7 (2)C13B—C8B—C9B—C10B2.0 (2)
C7A—C8A—C9A—C10A178.86 (12)C7B—C8B—C9B—C10B−178.11 (12)
F1A—C9A—C10A—C11A−179.58 (11)F1B—C9B—C10B—C11B179.72 (12)
C8A—C9A—C10A—C11A0.8 (2)C8B—C9B—C10B—C11B−0.6 (2)
C24A—O5A—C11A—C10A−5.89 (19)C24B—O5B—C11B—C12B5.1 (2)
C24A—O5A—C11A—C12A173.63 (12)C24B—O5B—C11B—C10B−175.45 (12)
C9A—C10A—C11A—O5A−179.63 (12)C9B—C10B—C11B—O5B179.39 (12)
C9A—C10A—C11A—C12A0.86 (19)C9B—C10B—C11B—C12B−1.1 (2)
O5A—C11A—C12A—C13A178.95 (12)O5B—C11B—C12B—C13B−179.19 (13)
C10A—C11A—C12A—C13A−1.5 (2)C10B—C11B—C12B—C13B1.4 (2)
C11A—C12A—C13A—C8A0.5 (2)C11B—C12B—C13B—C8B0.1 (2)
C9A—C8A—C13A—C12A0.98 (19)C9B—C8B—C13B—C12B−1.7 (2)
C7A—C8A—C13A—C12A−179.59 (12)C7B—C8B—C13B—C12B178.40 (13)
C16A—O2A—C15A—O3A2.8 (2)C16B—O2B—C15B—O3B0.88 (19)
C16A—O2A—C15A—C3A−175.94 (11)C16B—O2B—C15B—C3B−179.27 (11)
C2A—C3A—C15A—O3A1.8 (2)C2B—C3B—C15B—O3B−1.6 (2)
C4A—C3A—C15A—O3A−173.06 (14)C4B—C3B—C15B—O3B176.18 (13)
C2A—C3A—C15A—O2A−179.61 (12)C2B—C3B—C15B—O2B178.59 (12)
C4A—C3A—C15A—O2A5.58 (16)C4B—C3B—C15B—O2B−3.66 (15)
N1A—C4A—C17A—C18A−76.38 (15)N1B—C4B—C17B—C18B65.35 (16)
C3A—C4A—C17A—C18A43.75 (17)C3B—C4B—C17B—C18B−55.52 (17)
N1A—C4A—C17A—C22A102.51 (14)N1B—C4B—C17B—C22B−115.06 (14)
C3A—C4A—C17A—C22A−137.36 (13)C3B—C4B—C17B—C22B124.07 (14)
C22A—C17A—C18A—C19A−1.0 (2)C22B—C17B—C18B—C19B0.6 (2)
C4A—C17A—C18A—C19A177.95 (12)C4B—C17B—C18B—C19B−179.81 (13)
C17A—C18A—C19A—C20A0.3 (2)C17B—C18B—C19B—C20B−0.5 (2)
C23A—O4A—C20A—C19A2.7 (2)C23B—O4B—C20B—C19B6.1 (2)
C23A—O4A—C20A—C21A−177.20 (13)C23B—O4B—C20B—C21B−173.95 (13)
C18A—C19A—C20A—O4A−179.44 (13)C18B—C19B—C20B—O4B−179.75 (13)
C18A—C19A—C20A—C21A0.4 (2)C18B—C19B—C20B—C21B0.3 (2)
O4A—C20A—C21A—C22A179.41 (13)O4B—C20B—C21B—C22B179.88 (13)
C19A—C20A—C21A—C22A−0.5 (2)C19B—C20B—C21B—C22B−0.2 (2)
C20A—C21A—C22A—C17A−0.2 (2)C20B—C21B—C22B—C17B0.2 (2)
C18A—C17A—C22A—C21A0.9 (2)C18B—C17B—C22B—C21B−0.5 (2)
C4A—C17A—C22A—C21A−178.01 (13)C4B—C17B—C22B—C21B179.95 (13)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17A–C22A ring.
D—H···AD—HH···AD···AD—H···A
C12A—H12A···O1Bi0.952.523.4472 (18)166
C13A—H13A···S1A0.952.553.2321 (18)129
C13B—H13B···S1B0.952.543.2578 (19)133
C14A—H14A···O3A0.982.172.927 (2)133
C14B—H14D···O3B0.982.152.8820 (19)130
C18A—H18A···O3Bii0.952.583.249 (2)128
C21A—H21A···F1Biii0.952.483.2047 (18)134
C24A—H24C···O3B0.982.483.2724 (19)137
C24A—H24A···Cg1iv0.982.503.3612 (19)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2738).

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