Ethyl 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methyl­ene)-3-oxo-5-phenyl-3,5-dihydro-2H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Hu, J.; Wu, X.-X.; Shen, X.-Q.; Tang, L.-G.; Li, X.-K.

doi:10.1107/S1600536812041748

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3099

doi:10.1107/S1600536812041748

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Ethyl 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methylene)-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Jie Hu,^a Xi-Xi Wu,^a Xue-Qian Shen,^a Long-Guang Tang ^a and Xiao-Kun Li ^a ^*

^aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
^*Correspondence e-mail: proflxk@163.com

(Received 1 September 2012; accepted 5 October 2012; online 10 October 2012)

In the structure of the title compound, C₂₂H₂₁N₃O₃S, the thiazole ring forms dihedral angles of 88.83 (7) and 9.39 (9)°, respectively, with the benzene and pyrrole rings. The dihydropyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z conformation.

Related literature

For related structures, see: Hou (2009 ); Zhao et al. (2011 ). For background to the biological properties of fused thiazolo[3,2-a]pyrimidine derivatives, see: Ashok et al. (2007 ); Bahekar & Shinde (2004 ); Hurst & Hull (1961 ); Mehta et al. (2006 ); Shah & Desai (2007 ); Srivastava et al. (2006 ); Subudhi et al. (2007 ); Magerramov et al. (2006 ); Zhou et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₁N₃O₃S
M_r = 407.48
Monoclinic, P 2₁ /n
a = 11.8187 (10) Å
b = 10.2911 (9) Å
c = 16.2290 (14) Å
β = 90.584 (2)°
V = 1973.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.32 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.814, T_max = 1.000
10415 measured reflections
3877 independent reflections
3433 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.05
3877 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.19 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, New_Global_Publ_Block. DOI: 10.1107/S1600536812041748/aa2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041748/aa2075Isup2.hkl

checkCIF report

Comment top

Thiazolinone and their derivatives have attracted continuing interest over the years because of their varied biological activities (Shah & Desai,2007), such as antifungal (Mehta et al., 2006), antibacterial (Subudhi et al., 2007), anti-tumor (Zhou et al., 2008), anti-HIV and anti-inflammatory (Srivastava et al., 2006). 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) are known for more than a century and have attracted considerable attention because of their wide spectrum of therapeutic and pharmacological properties. DHPMs have been used as antibacterial, antifungal (Ashok et al., 2007), antiviral (Hurst & Hull, 1961), anti-inflammatory (Bahekar & Shinde, 2004), antioxidative properties and noteworthy, as well as calcium channel modulators (Magerramov et al., 2006). Herein, we report in the present work based on the pharmacological principle of stacking, such biologically active groups as DHPMs was introduced to thiazolinone, with a view to get new compounds with better bioactivity.

In continuation of our studies on heterocyclic compounds, we report the crystal structure of the title compound. The fused thiazole ring has usual geometry as observed in other thiazolo[3,2-a]pyrimidine compounds (Hou, 2009; Zhao et al., 2011). The thiazole ring makes dihedral angles of 88.83 (7) and 9.39 (9)° with the benzene ring and pyrrole ring, respectively. The pyrimidine ring adopts a flattened boat conformation. The C2–C17 distance, 1.345 (2) Å, confirms this as a double bond and the molecule adopts a Z conformation with respect to this bond (Fig. 1).

Related literature top

For related structures, see: Hou (2009); Zhao et al. (2011). For background to the biological properties of fused thiazolo[3,2-a]pyrimidine derivatives, see: Ashok et al. (2007); Bahekar & Shinde (2004); Hurst & Hull (1961); Mehta et al. (2006); Shah & Desai (2007); Srivastava et al. (2006); Subudhi et al. (2007); Magerramov et al. (2006); Zhou et al. (2008).

Experimental top

In a typical procedure of one pot Biginelli reaction, sulfamic acid (0.4 mol) was added to a solution of substituted benzaldehyde (0.5 mol), ethyl acetylacetate (0.6 mol), and thiourea (0.75 mol) in ethanol and reflux at 351 K for 2 h. When the reaction was finished, the mixture was cooled to room temperature and filtered. The product ethyl 2-mercapto-4-methyl-6 -phenyl-1,6-dihydropyrimidine-5-carboxylate was washed with water, and then dried in vacuum as a white solid.

To a stirred solution of ethyl ] 2-mercapto-4-methyl-6-phenyl-1,6-dihydropyrimidine-5-carboxylate (2 mmol) and ethyl chloroacetate (2 mmol) in ethanol (10 ml) pyridine (2 mmol) was added.The reaction was heated at refluxing temperature for 4 h. Then 1-methyl-1H-pyrrole-2-carbaldehyde (2 mmol) and morpholine (2 mmol) was added to the mixture without further treatment until the reaction finished. The mixture was then cooled to room temperature, filtered and washed with water to obtain crude product. The resulting yellow solid was collected and recrystallized from acetic acid, then single crystals were grown in CH₂Cl₂/CH₃OH mixture (2:1). Yield 45.6%.

¹H NMR (DMSO-d₆) δ: 1.111 (3H, m, 6–CH₃), 4.030 (2H, m, 6–CH₂), 2.380 (3H, s, N–CH₃), 3.730 (3H, s, 7–CH₃), 6.035 (H, s, 5–CH), 6.317 (1H, m, pyrrole), 6.576(1H, m, pyrrole), 7.213 (1H, m, pyrrole), 7.284–7.340 (5H, m, Ar—H), 7.625 (1H, s, =CH). ESI-MS m/z: 408.4 (M)⁺, 430.3 (M+Na)⁺, calcd for C₂₂H₂₁N₃O₃S 407.49.

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methylene)-3-oxo-5- phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate top

Crystal data top

C₂₂H₂₁N₃O₃S	F(000) = 856
M_r = 407.48	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4867 reflections
a = 11.8187 (10) Å	θ = 5.0–56.3°
b = 10.2911 (9) Å	µ = 0.19 mm⁻¹
c = 16.2290 (14) Å	T = 293 K
β = 90.584 (2)°	Prismatic, red
V = 1973.8 (3) Å³	0.32 × 0.24 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3877 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
T_min = 0.814, T_max = 1.000	k = −12→11
10415 measured reflections	l = −20→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0574P)² + 0.5784P] where P = (F_o² + 2F_c²)/3
3877 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₁N₃O₃S	V = 1973.8 (3) Å³
M_r = 407.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8187 (10) Å	µ = 0.19 mm⁻¹
b = 10.2911 (9) Å	T = 293 K
c = 16.2290 (14) Å	0.32 × 0.24 × 0.16 mm
β = 90.584 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3877 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3433 reflections with I > 2σ(I)
T_min = 0.814, T_max = 1.000	R_int = 0.020
10415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3877 reflections	Δρ_min = −0.19 e Å⁻³
265 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	0.45859 (3)	0.25287 (4)	0.01131 (2)	0.04128 (14)
N1	0.36364 (10)	0.46192 (12)	0.06560 (7)	0.0318 (3)
N2	0.26786 (11)	0.35881 (14)	−0.04481 (8)	0.0402 (3)
N3	0.76832 (11)	0.15037 (14)	0.18041 (8)	0.0413 (3)
O1	0.48083 (10)	0.52724 (11)	0.17107 (8)	0.0471 (3)
O2	0.05024 (13)	0.69653 (15)	−0.05111 (10)	0.0735 (5)
O3	0.14144 (10)	0.76092 (11)	0.06154 (7)	0.0473 (3)
C1	0.45910 (12)	0.45135 (15)	0.11618 (9)	0.0337 (3)
C2	0.52334 (12)	0.33419 (15)	0.09404 (9)	0.0343 (3)
C3	0.34879 (12)	0.36725 (15)	0.00763 (9)	0.0338 (3)
C4	0.19135 (13)	0.46391 (15)	−0.04784 (9)	0.0362 (3)
C5	0.19370 (12)	0.56033 (15)	0.00841 (9)	0.0336 (3)
C6	0.27014 (12)	0.55164 (14)	0.08448 (9)	0.0316 (3)
H6	0.3014	0.6379	0.0965	0.038*
C7	0.20515 (11)	0.50354 (15)	0.15961 (9)	0.0330 (3)
C8	0.16948 (14)	0.59098 (18)	0.21843 (10)	0.0446 (4)
H8	0.1883	0.6784	0.2138	0.054*
C9	0.10566 (17)	0.5486 (2)	0.28426 (11)	0.0588 (5)
H9	0.0809	0.6081	0.3233	0.071*
C10	0.07856 (16)	0.4197 (2)	0.29245 (11)	0.0573 (5)
H10	0.0360	0.3919	0.3370	0.069*
C11	0.11433 (15)	0.3322 (2)	0.23496 (11)	0.0520 (4)
H11	0.0967	0.2446	0.2406	0.062*
C12	0.17686 (14)	0.37389 (17)	0.16826 (10)	0.0422 (4)
H12	0.2001	0.3141	0.1289	0.051*
C13	0.11228 (15)	0.45209 (19)	−0.12025 (11)	0.0485 (4)
H13A	0.0502	0.5112	−0.1137	0.073*
H13B	0.0840	0.3648	−0.1235	0.073*
H13C	0.1520	0.4728	−0.1699	0.073*
C14	0.12023 (13)	0.67570 (16)	0.00121 (10)	0.0396 (4)
C15	0.07470 (16)	0.87886 (19)	0.05991 (13)	0.0561 (5)
H15A	−0.0034	0.8591	0.0727	0.067*
H15B	0.0768	0.9173	0.0054	0.067*
C16	0.1209 (2)	0.9705 (3)	0.12081 (18)	0.0907 (9)
H16A	0.1136	0.9345	0.1751	0.136*
H16B	0.0799	1.0509	0.1176	0.136*
H16C	0.1993	0.9861	0.1096	0.136*
C17	0.61539 (12)	0.29575 (16)	0.13690 (10)	0.0371 (3)
H17	0.6411	0.3529	0.1773	0.045*
C18	0.67851 (12)	0.17881 (16)	0.12828 (10)	0.0384 (4)
C19	0.66600 (15)	0.07268 (18)	0.07624 (12)	0.0503 (4)
H19	0.6123	0.0643	0.0343	0.060*
C20	0.74750 (17)	−0.01876 (19)	0.09753 (13)	0.0572 (5)
H20	0.7581	−0.0994	0.0729	0.069*
C21	0.80908 (15)	0.03176 (18)	0.16125 (12)	0.0516 (4)
H21	0.8697	−0.0091	0.1875	0.062*
C22	0.81581 (16)	0.23339 (19)	0.24420 (13)	0.0548 (5)
H22A	0.8705	0.1853	0.2760	0.082*
H22B	0.7565	0.2628	0.2796	0.082*
H22C	0.8518	0.3069	0.2192	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0416 (2)	0.0415 (2)	0.0407 (2)	0.01238 (17)	−0.00433 (17)	−0.00727 (16)
N1	0.0271 (6)	0.0325 (7)	0.0358 (6)	0.0032 (5)	−0.0009 (5)	−0.0010 (5)
N2	0.0418 (7)	0.0412 (8)	0.0373 (7)	0.0070 (6)	−0.0067 (6)	−0.0036 (6)
N3	0.0334 (7)	0.0417 (8)	0.0488 (8)	0.0044 (6)	−0.0002 (6)	0.0088 (6)
O1	0.0408 (6)	0.0430 (7)	0.0573 (7)	0.0047 (5)	−0.0145 (5)	−0.0128 (6)
O2	0.0766 (10)	0.0619 (9)	0.0813 (10)	0.0293 (8)	−0.0421 (8)	−0.0117 (8)
O3	0.0500 (7)	0.0418 (7)	0.0499 (7)	0.0171 (5)	−0.0098 (5)	−0.0021 (5)
C1	0.0281 (7)	0.0335 (8)	0.0396 (8)	−0.0014 (6)	−0.0007 (6)	0.0012 (6)
C2	0.0296 (7)	0.0346 (8)	0.0388 (8)	0.0004 (6)	0.0019 (6)	0.0010 (6)
C3	0.0346 (7)	0.0338 (8)	0.0331 (7)	0.0041 (6)	0.0019 (6)	0.0005 (6)
C4	0.0334 (7)	0.0393 (8)	0.0359 (7)	0.0015 (6)	−0.0023 (6)	0.0039 (6)
C5	0.0289 (7)	0.0357 (8)	0.0363 (7)	0.0019 (6)	−0.0008 (6)	0.0055 (6)
C6	0.0283 (7)	0.0288 (7)	0.0376 (8)	0.0036 (6)	−0.0016 (6)	−0.0014 (6)
C7	0.0263 (7)	0.0398 (8)	0.0328 (7)	0.0047 (6)	−0.0051 (6)	−0.0007 (6)
C8	0.0474 (9)	0.0451 (10)	0.0413 (9)	0.0062 (8)	−0.0028 (7)	−0.0075 (7)
C9	0.0566 (11)	0.0806 (15)	0.0395 (9)	0.0131 (10)	0.0064 (8)	−0.0122 (9)
C10	0.0463 (10)	0.0845 (16)	0.0412 (9)	0.0007 (10)	0.0076 (8)	0.0094 (9)
C11	0.0436 (9)	0.0572 (11)	0.0554 (10)	−0.0039 (8)	0.0033 (8)	0.0114 (9)
C12	0.0403 (8)	0.0430 (9)	0.0433 (9)	0.0009 (7)	0.0033 (7)	−0.0006 (7)
C13	0.0467 (9)	0.0545 (11)	0.0442 (9)	0.0063 (8)	−0.0121 (7)	−0.0035 (8)
C14	0.0358 (8)	0.0402 (9)	0.0427 (8)	0.0044 (7)	−0.0033 (7)	0.0062 (7)
C15	0.0539 (11)	0.0439 (10)	0.0703 (12)	0.0189 (8)	−0.0066 (9)	−0.0017 (9)
C16	0.0925 (18)	0.0751 (17)	0.1037 (19)	0.0376 (14)	−0.0330 (15)	−0.0384 (14)
C17	0.0305 (7)	0.0371 (8)	0.0437 (8)	0.0001 (6)	−0.0004 (6)	0.0003 (7)
C18	0.0294 (7)	0.0393 (9)	0.0465 (9)	0.0029 (6)	0.0007 (6)	0.0054 (7)
C19	0.0444 (9)	0.0479 (10)	0.0584 (11)	0.0083 (8)	−0.0045 (8)	−0.0052 (8)
C20	0.0566 (11)	0.0425 (10)	0.0725 (13)	0.0140 (9)	0.0016 (10)	−0.0040 (9)
C21	0.0438 (9)	0.0447 (10)	0.0663 (12)	0.0142 (8)	0.0024 (8)	0.0129 (9)
C22	0.0479 (10)	0.0532 (11)	0.0628 (12)	0.0022 (8)	−0.0167 (9)	0.0072 (9)

Geometric parameters (Å, º) top

S1—C2	1.7515 (15)	C9—H9	0.9300
S1—C3	1.7525 (15)	C10—C11	1.367 (3)
N1—C3	1.3644 (19)	C10—H10	0.9300
N1—C1	1.3927 (18)	C11—C12	1.385 (2)
N1—C6	1.4747 (18)	C11—H11	0.9300
N2—C3	1.2767 (19)	C12—H12	0.9300
N2—C4	1.410 (2)	C13—H13A	0.9600
N3—C21	1.350 (2)	C13—H13B	0.9600
N3—C18	1.382 (2)	C13—H13C	0.9600
N3—C22	1.451 (2)	C15—C16	1.467 (3)
O1—C1	1.2103 (18)	C15—H15A	0.9700
O2—C14	1.1986 (19)	C15—H15B	0.9700
O3—C14	1.336 (2)	C16—H16A	0.9600
O3—C15	1.448 (2)	C16—H16B	0.9600
C1—C2	1.471 (2)	C16—H16C	0.9600
C2—C17	1.345 (2)	C17—C18	1.424 (2)
C4—C5	1.348 (2)	C17—H17	0.9300
C4—C13	1.499 (2)	C18—C19	1.388 (2)
C5—C14	1.475 (2)	C19—C20	1.388 (3)
C5—C6	1.525 (2)	C19—H19	0.9300
C6—C7	1.530 (2)	C20—C21	1.362 (3)
C6—H6	0.9800	C20—H20	0.9300
C7—C8	1.381 (2)	C21—H21	0.9300
C7—C12	1.383 (2)	C22—H22A	0.9600
C8—C9	1.384 (3)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.371 (3)

C2—S1—C3	91.30 (7)	C7—C12—C11	120.65 (16)
C3—N1—C1	116.64 (12)	C7—C12—H12	119.7
C3—N1—C6	119.93 (12)	C11—C12—H12	119.7
C1—N1—C6	122.05 (12)	C4—C13—H13A	109.5
C3—N2—C4	116.54 (13)	C4—C13—H13B	109.5
C21—N3—C18	108.92 (15)	H13A—C13—H13B	109.5
C21—N3—C22	124.10 (15)	C4—C13—H13C	109.5
C18—N3—C22	126.96 (14)	H13A—C13—H13C	109.5
C14—O3—C15	116.02 (13)	H13B—C13—H13C	109.5
O1—C1—N1	123.23 (14)	O2—C14—O3	121.64 (15)
O1—C1—C2	127.04 (14)	O2—C14—C5	126.98 (16)
N1—C1—C2	109.69 (12)	O3—C14—C5	111.37 (13)
C17—C2—C1	122.10 (14)	O3—C15—C16	109.13 (16)
C17—C2—S1	126.93 (13)	O3—C15—H15A	109.9
C1—C2—S1	110.87 (10)	C16—C15—H15A	109.9
N2—C3—N1	126.75 (14)	O3—C15—H15B	109.9
N2—C3—S1	121.76 (12)	C16—C15—H15B	109.9
N1—C3—S1	111.48 (10)	H15A—C15—H15B	108.3
C5—C4—N2	122.14 (13)	C15—C16—H16A	109.5
C5—C4—C13	126.79 (15)	C15—C16—H16B	109.5
N2—C4—C13	111.07 (14)	H16A—C16—H16B	109.5
C4—C5—C14	122.06 (14)	C15—C16—H16C	109.5
C4—C5—C6	120.85 (13)	H16A—C16—H16C	109.5
C14—C5—C6	117.05 (13)	H16B—C16—H16C	109.5
N1—C6—C5	107.91 (11)	C2—C17—C18	128.30 (15)
N1—C6—C7	110.27 (12)	C2—C17—H17	115.8
C5—C6—C7	111.47 (11)	C18—C17—H17	115.8
N1—C6—H6	109.0	N3—C18—C19	106.40 (14)
C5—C6—H6	109.0	N3—C18—C17	121.26 (15)
C7—C6—H6	109.0	C19—C18—C17	132.26 (15)
C8—C7—C12	118.85 (15)	C18—C19—C20	108.23 (17)
C8—C7—C6	119.96 (15)	C18—C19—H19	125.9
C12—C7—C6	121.13 (13)	C20—C19—H19	125.9
C7—C8—C9	120.06 (18)	C21—C20—C19	107.12 (17)
C7—C8—H8	120.0	C21—C20—H20	126.4
C9—C8—H8	120.0	C19—C20—H20	126.4
C10—C9—C8	120.59 (18)	N3—C21—C20	109.33 (16)
C10—C9—H9	119.7	N3—C21—H21	125.3
C8—C9—H9	119.7	C20—C21—H21	125.3
C11—C10—C9	119.81 (17)	N3—C22—H22A	109.5
C11—C10—H10	120.1	N3—C22—H22B	109.5
C9—C10—H10	120.1	H22A—C22—H22B	109.5
C10—C11—C12	120.04 (19)	N3—C22—H22C	109.5
C10—C11—H11	120.0	H22A—C22—H22C	109.5
C12—C11—H11	120.0	H22B—C22—H22C	109.5

C3—N1—C1—O1	−178.40 (14)	C5—C6—C7—C8	−101.17 (16)
C6—N1—C1—O1	−11.8 (2)	N1—C6—C7—C12	−43.80 (18)
C3—N1—C1—C2	−0.46 (18)	C5—C6—C7—C12	76.03 (17)
C6—N1—C1—C2	166.11 (12)	C12—C7—C8—C9	−0.6 (2)
O1—C1—C2—C17	2.4 (2)	C6—C7—C8—C9	176.68 (15)
N1—C1—C2—C17	−175.41 (14)	C7—C8—C9—C10	0.9 (3)
O1—C1—C2—S1	179.05 (14)	C8—C9—C10—C11	−0.3 (3)
N1—C1—C2—S1	1.22 (15)	C9—C10—C11—C12	−0.6 (3)
C3—S1—C2—C17	175.15 (15)	C8—C7—C12—C11	−0.3 (2)
C3—S1—C2—C1	−1.27 (11)	C6—C7—C12—C11	−177.55 (14)
C4—N2—C3—N1	5.9 (2)	C10—C11—C12—C7	0.9 (3)
C4—N2—C3—S1	−173.22 (11)	C15—O3—C14—O2	0.3 (2)
C1—N1—C3—N2	−179.70 (15)	C15—O3—C14—C5	179.36 (14)
C6—N1—C3—N2	13.4 (2)	C4—C5—C14—O2	2.3 (3)
C1—N1—C3—S1	−0.50 (16)	C6—C5—C14—O2	−175.46 (18)
C6—N1—C3—S1	−167.38 (10)	C4—C5—C14—O3	−176.79 (14)
C2—S1—C3—N2	−179.73 (14)	C6—C5—C14—O3	5.49 (19)
C2—S1—C3—N1	1.03 (11)	C14—O3—C15—C16	−170.47 (19)
C3—N2—C4—C5	−8.6 (2)	C1—C2—C17—C18	172.86 (15)
C3—N2—C4—C13	170.92 (14)	S1—C2—C17—C18	−3.2 (3)
N2—C4—C5—C14	174.67 (14)	C21—N3—C18—C19	−0.08 (18)
C13—C4—C5—C14	−4.7 (2)	C22—N3—C18—C19	178.08 (16)
N2—C4—C5—C6	−7.7 (2)	C21—N3—C18—C17	177.00 (14)
C13—C4—C5—C6	172.92 (15)	C22—N3—C18—C17	−4.8 (2)
C3—N1—C6—C5	−26.08 (17)	C2—C17—C18—N3	−176.53 (15)
C1—N1—C6—C5	167.78 (13)	C2—C17—C18—C19	−0.3 (3)
C3—N1—C6—C7	95.89 (15)	N3—C18—C19—C20	0.3 (2)
C1—N1—C6—C7	−70.25 (17)	C17—C18—C19—C20	−176.32 (17)
C4—C5—C6—N1	23.55 (19)	C18—C19—C20—C21	−0.4 (2)
C14—C5—C6—N1	−158.71 (12)	C18—N3—C21—C20	−0.2 (2)
C4—C5—C6—C7	−97.67 (16)	C22—N3—C21—C20	−178.41 (17)
C14—C5—C6—C7	80.07 (16)	C19—C20—C21—N3	0.4 (2)
N1—C6—C7—C8	139.00 (14)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁N₃O₃S
M_r	407.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.8187 (10), 10.2911 (9), 16.2290 (14)
β (°)	90.584 (2)
V (Å³)	1973.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.32 × 0.24 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.814, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10415, 3877, 3433
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.05
No. of reflections	3877
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.19

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

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grants No. LY12H16003 and Y4110197) and the project of Wenzhou Sci & Tech Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged for the data collection.

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