Ethyl (Z)-2-(2-fluoro­benzyl­idene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Zhao, C.-G.; Hu, J.; Zhang, Y.-L.; Zhang, J.; Yang, S.-L.

doi:10.1107/S1600536811042899

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3009

doi:10.1107/S1600536811042899

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Ethyl (Z)-2-(2-fluorobenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Cheng-Guang Zhao,^a,^b Jie Hu,^b Ya-Li Zhang,^a Jing Zhang ^a and Shu-Lin Yang ^a ^*

^aInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China, and ^bSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China
^*Correspondence e-mail: shulin_yang@126.com

(Received 13 October 2011; accepted 17 October 2011; online 22 October 2011)

The title compound, C₂₃H₁₉FN₂O₃S, a fused-pyrimidine derivative, displays dihedral angles between the thiazole ring and the benzene ring and substituted benzene ring of 7.10 (14) and 3.48 (12)°, respectively. The dihydropyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

Related literature

For related crystal structures, see: Hou (2009 ); Kulakov et al. (2009 ). For background to the biological properties of fused-pyrimidine derivatives, see: Alam et al. (2010 ); Al-Rashood & Abdel-Aziz (2010 ); Ashok et al. (2007 ); Jang et al. (2011 ); Wichmann et al. (1999 );. Zhou et al. (2011 ).

Experimental

Crystal data

C₂₃H₁₉FN₂O₃S
M_r = 422.46
Monoclinic, P 2₁ /n
a = 9.3230 (19) Å
b = 10.170 (2) Å
c = 21.862 (4) Å
β = 96.33 (3)°
V = 2060.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.26 × 0.17 × 0.13 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.831, T_max = 1.000
10963 measured reflections
4040 independent reflections
2918 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.147
S = 1.04
4040 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042899/ng5248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042899/ng5248Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042899/ng5248Isup3.cml

checkCIF report

Comment top

Pyrimidine derivatives are important molecules owing to their useful biological and therapeutic activities (Ashok et al., 2007; Zhou et al., 2011). Thiazole derivatives have similar useful activity (Jang et al., 2011). Such structural units are found in a vast number of naturally-occurring compounds and pharmaceuticals, so that the presence of both pyrimidine and thiazole rings give rise to enhanced activity (Al-Rashood & Abdel-Aziz, 2010; Wichmann et al., 1999; Alam et al., 2010).

In continuation of our studies on heterocyclic compounds, we report the crystal structure of (I). The fused thiazole ring has usual geometry as observed in other fused thiazolopyrimidine compounds (Hou, 2009; Kulakov et al., 2009). The thiazole ring makes dihedral angles of 87.10 (14) and 3.48 (12) ° with the benzene rings C14–C17 and C8–C13, respectively. The pyrimidine ring adopts a flattened boat conformation. The C2—C7 double bond exist in the Z configuration. The crystal packing is stabilized by π-π stacking interactions. (Fig. 1).

Related literature top

For related crystal structures, see: Hou, (2009); Kulakov et al. (2009). For background to the biological properties of fused-pyrimidine derivatives, see: Alam et al. (2010); Al-Rashood & Abdel-Aziz (2010); Ashok et al. (2007); Jang et al. (2011); Wichmann et al. (1999);. Zhou et al. (2011).

Experimental top

In a one-pot Biginelli reaction, a mixture of 5 mmol of benzaldehyde, 6 mmol e thyl acetoacetate, 7.5 mmol thiourea and 10 ml of EtOH was stirred at 50°C in presence of sulfamic acid catalyst for 3 h to obtain 6-methyl-4-phenyl-2-thioxo-1,2,3,4- tetrahydropyrimidine-5-carboxylate. The product (2 mmol) was reacted with ethyl chloroacetate (2 mmol) in presence of pyridine for 4 h; 2-fluorobenzaldehyde (2 mmol) and piperidine were added, and and the mixture refluxed for 4 h until the TLC assay indicated that the reaction was completed. The reaction mixture was cooled and filtered to give the crude product. The solid was recystallized from acetic acid, and single crystals were grown in a CH₂Cl₂/CH₃OH mixture (5:2 v/v)..

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHEXLTL (Bruker, 2002).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius.

Ethyl (Z)-2-(2-fluorobenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro- 2H-thiazolo[3,2-a]pyrimidine-6-carboxylate top

Crystal data top

C₂₃H₁₉FN₂O₃S	F(000) = 880
M_r = 422.46	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3230 (19) Å	Cell parameters from 2127 reflections
b = 10.170 (2) Å	θ = 2.5–24.0°
c = 21.862 (4) Å	µ = 0.19 mm⁻¹
β = 96.33 (3)°	T = 293 K
V = 2060.3 (7) Å³	Prismatic, green
Z = 4	0.26 × 0.17 × 0.13 mm

Data collection top

Bruker SMART diffractometer	4040 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
T_min = 0.831, T_max = 1.000	k = −11→12
10963 measured reflections	l = −21→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0733P)² + 0.4206P] where P = (F_o² + 2F_c²)/3
4040 reflections	(Δ/σ)_max = 0.009
273 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₃H₁₉FN₂O₃S	V = 2060.3 (7) Å³
M_r = 422.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3230 (19) Å	µ = 0.19 mm⁻¹
b = 10.170 (2) Å	T = 293 K
c = 21.862 (4) Å	0.26 × 0.17 × 0.13 mm
β = 96.33 (3)°

Data collection top

Bruker SMART diffractometer	4040 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2918 reflections with I > 2σ(I)
T_min = 0.831, T_max = 1.000	R_int = 0.027
10963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
4040 reflections	Δρ_min = −0.17 e Å⁻³
273 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

	x	y	z	U_iso*/U_eq
S1	0.12550 (6)	0.33812 (6)	1.02831 (3)	0.0515 (2)
N1	0.00474 (18)	0.31076 (17)	0.91699 (8)	0.0421 (4)
N2	−0.0764 (2)	0.16406 (19)	0.98954 (9)	0.0551 (5)
F1	0.46561 (19)	0.74388 (17)	0.96836 (8)	0.0873 (5)
O1	0.10315 (17)	0.47535 (17)	0.86461 (7)	0.0571 (4)
O2	−0.3636 (2)	0.0068 (2)	0.83596 (11)	0.0977 (7)
O3	−0.28690 (19)	0.1748 (2)	0.78413 (9)	0.0721 (5)
C1	0.0939 (2)	0.4181 (2)	0.91203 (10)	0.0423 (5)
C2	0.1745 (2)	0.4481 (2)	0.97289 (9)	0.0431 (5)
C3	0.0027 (2)	0.2577 (2)	0.97443 (10)	0.0455 (5)
C4	−0.0700 (2)	0.2454 (2)	0.86253 (10)	0.0476 (5)
H4	−0.1203	0.3121	0.8358	0.057*
C5	−0.1807 (2)	0.1507 (2)	0.88343 (11)	0.0499 (6)
C6	−0.1772 (2)	0.1125 (2)	0.94227 (12)	0.0536 (6)
C7	0.2703 (2)	0.5462 (2)	0.97837 (10)	0.0475 (5)
H7	0.2781	0.5930	0.9424	0.057*
C8	0.3638 (2)	0.5912 (2)	1.03149 (11)	0.0496 (6)
C9	0.3658 (3)	0.5407 (3)	1.09065 (12)	0.0632 (7)
H9	0.3031	0.4727	1.0979	0.076*
C10	0.4586 (3)	0.5889 (3)	1.13895 (13)	0.0768 (9)
H10	0.4578	0.5534	1.1781	0.092*
C11	0.5515 (3)	0.6883 (3)	1.12944 (16)	0.0795 (9)
H11	0.6140	0.7202	1.1622	0.095*
C12	0.5536 (3)	0.7414 (3)	1.07228 (15)	0.0747 (8)
H12	0.6164	0.8096	1.0657	0.090*
C13	0.4611 (3)	0.6919 (3)	1.02485 (13)	0.0588 (6)
C14	0.0385 (3)	0.1753 (3)	0.82699 (11)	0.0574 (7)
C15	0.0600 (3)	0.2140 (3)	0.76873 (13)	0.0809 (9)
H15	0.0088	0.2847	0.7504	0.097*
C16	0.1604 (5)	0.1456 (5)	0.73671 (18)	0.1075 (14)
H16	0.1754	0.1707	0.6970	0.129*
C17	0.2346 (4)	0.0434 (5)	0.7641 (2)	0.1163 (17)
H17	0.3004	−0.0013	0.7428	0.140*
C18	0.2155 (3)	0.0046 (4)	0.8219 (2)	0.1027 (13)
H18	0.2684	−0.0653	0.8402	0.123*
C19	0.1160 (3)	0.0704 (3)	0.85343 (15)	0.0768 (9)
H19	0.1014	0.0434	0.8929	0.092*
C20	−0.2869 (3)	0.1001 (3)	0.83382 (14)	0.0605 (7)
C21	−0.3860 (3)	0.1400 (4)	0.73092 (15)	0.0931 (11)
H21A	−0.3472	0.0674	0.7092	0.112*
H21B	−0.4777	0.1128	0.7439	0.112*
C22	−0.4067 (5)	0.2525 (5)	0.69102 (16)	0.1257 (15)
H22A	−0.4401	0.3254	0.7135	0.189*
H22B	−0.4769	0.2320	0.6569	0.189*
H22C	−0.3169	0.2751	0.6761	0.189*
C23	−0.2756 (3)	0.0149 (3)	0.96687 (15)	0.0743 (8)
H23A	−0.3639	0.0100	0.9399	0.111*
H23B	−0.2961	0.0418	1.0071	0.111*
H23C	−0.2300	−0.0699	0.9695	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0556 (4)	0.0553 (4)	0.0424 (3)	0.0045 (3)	−0.0004 (3)	0.0014 (3)
N1	0.0425 (10)	0.0440 (10)	0.0396 (9)	0.0018 (8)	0.0034 (7)	−0.0048 (8)
N2	0.0538 (12)	0.0497 (12)	0.0619 (13)	0.0032 (10)	0.0064 (10)	0.0065 (10)
F1	0.0901 (12)	0.0884 (12)	0.0848 (12)	−0.0292 (10)	0.0158 (9)	−0.0101 (9)
O1	0.0642 (10)	0.0621 (10)	0.0435 (9)	−0.0110 (8)	−0.0008 (7)	0.0053 (8)
O2	0.0845 (15)	0.0827 (15)	0.1215 (19)	−0.0357 (12)	−0.0082 (13)	−0.0088 (13)
O3	0.0576 (11)	0.0893 (14)	0.0668 (12)	−0.0195 (10)	−0.0052 (9)	−0.0159 (10)
C1	0.0424 (12)	0.0417 (12)	0.0423 (12)	0.0036 (9)	0.0027 (9)	−0.0044 (10)
C2	0.0434 (12)	0.0439 (12)	0.0413 (12)	0.0118 (10)	0.0023 (9)	−0.0061 (9)
C3	0.0439 (12)	0.0443 (12)	0.0487 (13)	0.0104 (10)	0.0063 (10)	0.0013 (10)
C4	0.0418 (12)	0.0527 (13)	0.0473 (12)	−0.0001 (10)	0.0004 (10)	−0.0083 (10)
C5	0.0360 (12)	0.0456 (12)	0.0684 (16)	0.0033 (10)	0.0076 (11)	−0.0087 (11)
C6	0.0433 (13)	0.0409 (12)	0.0772 (18)	0.0069 (10)	0.0091 (12)	0.0008 (12)
C7	0.0472 (12)	0.0469 (12)	0.0475 (12)	0.0075 (10)	0.0009 (10)	−0.0060 (10)
C8	0.0432 (12)	0.0501 (13)	0.0542 (14)	0.0116 (10)	−0.0009 (10)	−0.0119 (11)
C9	0.0656 (16)	0.0600 (16)	0.0605 (16)	0.0053 (13)	−0.0085 (12)	−0.0130 (12)
C10	0.081 (2)	0.082 (2)	0.0614 (17)	0.0164 (17)	−0.0211 (15)	−0.0173 (15)
C11	0.0549 (17)	0.088 (2)	0.090 (2)	0.0123 (16)	−0.0197 (15)	−0.0418 (18)
C12	0.0486 (15)	0.0779 (19)	0.095 (2)	0.0000 (14)	−0.0020 (15)	−0.0379 (17)
C13	0.0459 (13)	0.0580 (15)	0.0719 (17)	0.0036 (12)	0.0041 (12)	−0.0179 (13)
C14	0.0435 (13)	0.0694 (16)	0.0598 (15)	−0.0153 (12)	0.0084 (11)	−0.0282 (13)
C15	0.080 (2)	0.098 (2)	0.0684 (18)	−0.0322 (17)	0.0249 (15)	−0.0315 (16)
C16	0.106 (3)	0.132 (3)	0.094 (3)	−0.059 (3)	0.053 (2)	−0.055 (3)
C17	0.075 (2)	0.128 (4)	0.155 (4)	−0.037 (2)	0.056 (3)	−0.087 (3)
C18	0.0606 (19)	0.109 (3)	0.140 (3)	0.0046 (18)	0.020 (2)	−0.057 (3)
C19	0.0515 (15)	0.085 (2)	0.094 (2)	0.0080 (15)	0.0098 (14)	−0.0357 (17)
C20	0.0411 (13)	0.0565 (15)	0.0834 (19)	−0.0013 (12)	0.0050 (12)	−0.0158 (14)
C21	0.071 (2)	0.121 (3)	0.081 (2)	−0.0205 (19)	−0.0181 (17)	−0.026 (2)
C22	0.160 (4)	0.138 (4)	0.069 (2)	−0.015 (3)	−0.030 (2)	−0.018 (2)
C23	0.0620 (17)	0.0546 (16)	0.107 (2)	−0.0019 (13)	0.0147 (15)	0.0184 (15)

Geometric parameters (Å, º) top

S1—C2	1.746 (2)	C10—C11	1.361 (4)
S1—C3	1.752 (2)	C10—H10	0.9300
N1—C3	1.369 (3)	C11—C12	1.364 (4)
N1—C1	1.384 (3)	C11—H11	0.9300
N1—C4	1.470 (3)	C12—C13	1.369 (4)
N2—C3	1.270 (3)	C12—H12	0.9300
N2—C6	1.418 (3)	C14—C15	1.368 (4)
F1—C13	1.348 (3)	C14—C19	1.379 (4)
O1—C1	1.201 (3)	C15—C16	1.413 (5)
O2—C20	1.192 (3)	C15—H15	0.9300
O3—C20	1.326 (3)	C16—C17	1.351 (6)
O3—C21	1.448 (3)	C16—H16	0.9300
C1—C2	1.486 (3)	C17—C18	1.353 (6)
C2—C7	1.336 (3)	C17—H17	0.9300
C4—C5	1.518 (3)	C18—C19	1.387 (4)
C4—C14	1.520 (3)	C18—H18	0.9300
C4—H4	0.9800	C19—H19	0.9300
C5—C6	1.341 (3)	C21—C22	1.438 (5)
C5—C20	1.478 (3)	C21—H21A	0.9700
C6—C23	1.492 (3)	C21—H21B	0.9700
C7—C8	1.447 (3)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—C13	1.387 (4)	C22—H22C	0.9600
C8—C9	1.390 (4)	C23—H23A	0.9600
C9—C10	1.379 (4)	C23—H23B	0.9600
C9—H9	0.9300	C23—H23C	0.9600

C2—S1—C3	91.96 (11)	C13—C12—H12	120.8
C3—N1—C1	116.89 (18)	F1—C13—C12	118.0 (3)
C3—N1—C4	120.74 (18)	F1—C13—C8	118.2 (2)
C1—N1—C4	121.90 (18)	C12—C13—C8	123.8 (3)
C3—N2—C6	116.4 (2)	C15—C14—C19	119.3 (3)
C20—O3—C21	117.4 (2)	C15—C14—C4	121.0 (3)
O1—C1—N1	123.46 (19)	C19—C14—C4	119.7 (2)
O1—C1—C2	126.6 (2)	C14—C15—C16	119.5 (4)
N1—C1—C2	109.93 (19)	C14—C15—H15	120.2
C7—C2—C1	120.1 (2)	C16—C15—H15	120.2
C7—C2—S1	129.77 (17)	C17—C16—C15	119.6 (4)
C1—C2—S1	110.16 (16)	C17—C16—H16	120.2
N2—C3—N1	127.0 (2)	C15—C16—H16	120.2
N2—C3—S1	122.04 (18)	C16—C17—C18	121.7 (4)
N1—C3—S1	111.00 (16)	C16—C17—H17	119.2
N1—C4—C5	108.68 (18)	C18—C17—H17	119.2
N1—C4—C14	110.08 (17)	C17—C18—C19	119.1 (4)
C5—C4—C14	111.69 (19)	C17—C18—H18	120.4
N1—C4—H4	108.8	C19—C18—H18	120.4
C5—C4—H4	108.8	C14—C19—C18	120.9 (4)
C14—C4—H4	108.8	C14—C19—H19	119.6
C6—C5—C20	123.1 (2)	C18—C19—H19	119.6
C6—C5—C4	121.8 (2)	O2—C20—O3	122.9 (3)
C20—C5—C4	115.0 (2)	O2—C20—C5	127.2 (3)
C5—C6—N2	122.4 (2)	O3—C20—C5	109.9 (2)
C5—C6—C23	126.0 (2)	C22—C21—O3	108.9 (3)
N2—C6—C23	111.6 (2)	C22—C21—H21A	109.9
C2—C7—C8	130.2 (2)	O3—C21—H21A	109.9
C2—C7—H7	114.9	C22—C21—H21B	109.9
C8—C7—H7	114.9	O3—C21—H21B	109.9
C13—C8—C9	115.4 (2)	H21A—C21—H21B	108.3
C13—C8—C7	119.5 (2)	C21—C22—H22A	109.5
C9—C8—C7	125.1 (2)	C21—C22—H22B	109.5
C10—C9—C8	121.6 (3)	H22A—C22—H22B	109.5
C10—C9—H9	119.2	C21—C22—H22C	109.5
C8—C9—H9	119.2	H22A—C22—H22C	109.5
C11—C10—C9	120.2 (3)	H22B—C22—H22C	109.5
C11—C10—H10	119.9	C6—C23—H23A	109.5
C9—C10—H10	119.9	C6—C23—H23B	109.5
C10—C11—C12	120.5 (3)	H23A—C23—H23B	109.5
C10—C11—H11	119.7	C6—C23—H23C	109.5
C12—C11—H11	119.7	H23A—C23—H23C	109.5
C11—C12—C13	118.5 (3)	H23B—C23—H23C	109.5
C11—C12—H12	120.8

C3—N1—C1—O1	−178.3 (2)	S1—C2—C7—C8	0.6 (4)
C4—N1—C1—O1	9.5 (3)	C2—C7—C8—C13	176.4 (2)
C3—N1—C1—C2	2.4 (2)	C2—C7—C8—C9	−3.3 (4)
C4—N1—C1—C2	−169.82 (17)	C13—C8—C9—C10	0.2 (4)
O1—C1—C2—C7	−1.2 (3)	C7—C8—C9—C10	179.9 (2)
N1—C1—C2—C7	178.14 (18)	C8—C9—C10—C11	−0.1 (4)
O1—C1—C2—S1	−179.97 (19)	C9—C10—C11—C12	0.2 (4)
N1—C1—C2—S1	−0.6 (2)	C10—C11—C12—C13	−0.4 (4)
C3—S1—C2—C7	−179.4 (2)	C11—C12—C13—F1	−179.1 (2)
C3—S1—C2—C1	−0.79 (16)	C11—C12—C13—C8	0.6 (4)
C6—N2—C3—N1	−2.6 (3)	C9—C8—C13—F1	179.2 (2)
C6—N2—C3—S1	176.41 (16)	C7—C8—C13—F1	−0.5 (3)
C1—N1—C3—N2	176.1 (2)	C9—C8—C13—C12	−0.5 (4)
C4—N1—C3—N2	−11.6 (3)	C7—C8—C13—C12	179.8 (2)
C1—N1—C3—S1	−3.0 (2)	N1—C4—C14—C15	−115.2 (2)
C4—N1—C3—S1	169.30 (15)	C5—C4—C14—C15	124.0 (2)
C2—S1—C3—N2	−177.05 (19)	N1—C4—C14—C19	65.4 (3)
C2—S1—C3—N1	2.07 (16)	C5—C4—C14—C19	−55.4 (3)
C3—N1—C4—C5	19.3 (3)	C19—C14—C15—C16	0.2 (4)
C1—N1—C4—C5	−168.82 (18)	C4—C14—C15—C16	−179.2 (2)
C3—N1—C4—C14	−103.3 (2)	C14—C15—C16—C17	−0.4 (5)
C1—N1—C4—C14	68.6 (3)	C15—C16—C17—C18	−0.1 (6)
N1—C4—C5—C6	−16.0 (3)	C16—C17—C18—C19	0.8 (5)
C14—C4—C5—C6	105.6 (2)	C15—C14—C19—C18	0.4 (4)
N1—C4—C5—C20	166.70 (18)	C4—C14—C19—C18	179.8 (2)
C14—C4—C5—C20	−71.7 (2)	C17—C18—C19—C14	−0.9 (5)
C20—C5—C6—N2	−178.7 (2)	C21—O3—C20—O2	0.4 (4)
C4—C5—C6—N2	4.3 (3)	C21—O3—C20—C5	−179.5 (2)
C20—C5—C6—C23	0.5 (4)	C6—C5—C20—O2	−13.9 (4)
C4—C5—C6—C23	−176.5 (2)	C4—C5—C20—O2	163.4 (3)
C3—N2—C6—C5	6.2 (3)	C6—C5—C20—O3	166.0 (2)
C3—N2—C6—C23	−173.1 (2)	C4—C5—C20—O3	−16.8 (3)
C1—C2—C7—C8	−177.9 (2)	C20—O3—C21—C22	160.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.62	3.410 (5)	144
C23—H23C···S1ⁱⁱ	0.96	2.90	3.851 (3)	173

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉FN₂O₃S
M_r	422.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.3230 (19), 10.170 (2), 21.862 (4)
β (°)	96.33 (3)
V (Å³)	2060.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.26 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.831, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10963, 4040, 2918
R_int	0.027

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.147, 1.04
No. of reflections	4040
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2002), SHEXLTL (Bruker, 2002).

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grant No. Y4110197) and the Project of Wenzhou Science and Technology Bureau (grant No. Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences is gratefully acknowledged.

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