3-Ethyl­sulfanyl-5-methyl-1-phenyl-7-(pyrrolidin-1-yl)-1H-pyrimido[4,5-e][1,3,4]thia­diazine

Nikpour, M.; Bakavoli, M.; Rahimizadeh, M.; Bigdeli, M.R.; Mirzaei, M.

doi:10.1107/S1600536808021144

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1491

doi:10.1107/S1600536808021144

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3-Ethylsulfanyl-5-methyl-1-phenyl-7-(pyrrolidin-1-yl)-1H-pyrimido[4,5-e][1,3,4]thiadiazine

M. Nikpour,^a ^* M. Bakavoli,^b M. Rahimizadeh,^b M. R. Bigdeli ^a and M. Mirzaei ^b

^aDepartment of Chemistry, School of Sciences, Islamic Azad University, Ahvaz Branch, Ahvaz, Iran, and ^bDepartment of Chemistry, School of Sciences, Ferdowsi University, Mashhad, 917751436, Iran
^*Correspondence e-mail: nikpour_m@yahoo.com

(Received 3 June 2008; accepted 8 July 2008; online 16 July 2008)

In the crystal structure of the title compound, C₁₈H₂₁N₅S₂, the thiadiazine six-membered ring and pyrrolidine five-membered ring display boat and envelope conformations, respectively. The crystal structure contains weak C—H⋯N and C—H⋯S hydrogen bonding.

Related literature

For general background, see: Rahimizadeh et al. (1997 ); Elliott (1981 ); Bakavoli et al. (2006 , 2007 , 2008 ).

Experimental

Crystal data

C₁₈H₂₁N₅S₂
M_r = 371.52
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.3601 (2) Å
b = 10.3596 (3) Å
c = 20.5754 (6) Å
V = 1781.98 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 (2) K
0.43 × 0.34 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2005 ) T_min = 0.878, T_max = 0.926
36558 measured reflections
6479 independent reflections
5952 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.076
S = 1.01
6479 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 2828 Friedel pairs
Flack parameter: −0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯N4ⁱ	0.95	2.62	3.5630 (15)	172
C15—H15B⋯S2ⁱⁱ	0.99	2.83	3.6264 (13)	138
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021144/xu2431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021144/xu2431Isup2.hkl

checkCIF report

Comment top

The diverse biological activities of pyrimido [4,5-e][1,3,4]thiadiazine persuaded us to search for newer and more efficient synthetic methods for this class of heterocyclic compounds. These compounds have been described as being nucleoside analogues, anti-inflammatory, hypotensive, diuretic, and phosphodiesterase inhibitor agents. Despite their importance from pharmacological and synthetic point of views, comparatively few methods for their preparation have been reported. Pyrimido [4,5-e] [1,3,4]thiadiazines have been solely synthesized from pyrimidines. Previous routes to such systems have involved condensation of 2,4- dichloro–5-nitro -6-methylpyrimidine with dithizone (Rahimizadeh et al., 1997) via Smiles Rearrangement, heterocyclization of 6-hydrazino substituted uracils with isothiocyanates and N-bromosuccinimide, reaction of thiohydrazides with 4,5- dihalopyrimidines (Elliott, 1981), condensation of 5-bromo-2-chloro-6-methyl-4-(1-methylhydrazino) pyrimidine with carbondisulfide and alkylhalides (Bakavoli et al., 2007) and isothiocyanates (Bakavoli et al., 2008). In aprevious communication (Bakavoli et al., 2006), we described a new approach for the formation of 1-phenyl-1H-[1,3,4]thiadiazino[5,6-b]quinoxalines. The synthesis we developed involved heterocyclization of alkyl-2-phenylhydrazinecarbodithioates as bifunctional nucleophiles with 2,3-dichloroquinoxaline as an electrophile. To extend the scope of this strategy, we explored other electrophilic species that could successfully undergo similar reaction.

The molecular structure is shown in Fig. 1. In the title crystal structure, the thiadiazine six-membered ring and pyrrolidine five-membered ring display the boat and envelope configuration, respectively. The crystal structure contains weak C—H···N and C—H···S hydrogen bonding (Table 1).

Related literature top

For general background, see: Rahimizadeh et al. (1997); Elliott (1981); Bakavoli et al. (2006, 2007, 2008).

Experimental top

A mixture of 5-bromo2,4-dichloro-6-methylpyrimidine (2.5 mmol, 0.61 g), each alkyl-2-phenylhydrazinecarbodithioates (2.5 mmol) and triethylamine (1 ml) in acetonitril (10 ml) were boiled under inert atmosphere for 3 h. After the reaction was completed, the mixture was cooled to room temperature, and then evaporated under reduced pressure. The residue was washed with water and crystallized with ethanol and then washed with petroleum ether 40–60 to give pyrimido [4,5-e][1,3,4] thiadiazines. A mixture of previous obtained compound (5 mmol) in ethanol (20 ml) was heated under reflux with pyrrolidine (1.8 g) for 4 h. The solvent was removed and the residue was washed with water and then crystallized from ethanol to give the title crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 with 30% probability displacement (arbitrary spheres for H atoms).

3-Ethylsulfanyl-5-methyl-1-phenyl-7-pyrrolidin-1-yl-1H- pyrimido[4,5-e][1,3,4]thiadiazine top

Crystal data top

C₁₈H₂₁N₅S₂	D_x = 1.385 Mg m⁻³
M_r = 371.52	Melting point: 407 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9869 reflections
a = 8.3601 (2) Å	θ = 2.2–30.5°
b = 10.3596 (3) Å	µ = 0.31 mm⁻¹
c = 20.5754 (6) Å	T = 100 K
V = 1781.98 (8) Å³	Prism, colorless
Z = 4	0.43 × 0.34 × 0.25 mm
F(000) = 784

Data collection top

Bruker APEXII CCD area-detector diffractometer	6479 independent reflections
Radiation source: fine-focus sealed tube	5952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.0°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −12→12
T_min = 0.878, T_max = 0.927	k = −15→15
36558 measured reflections	l = −31→31

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.04P)² + 0.35P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
6479 reflections	Δρ_max = 0.39 e Å⁻³
228 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2828 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (4)

Crystal data top

C₁₈H₂₁N₅S₂	V = 1781.98 (8) Å³
M_r = 371.52	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.3601 (2) Å	µ = 0.31 mm⁻¹
b = 10.3596 (3) Å	T = 100 K
c = 20.5754 (6) Å	0.43 × 0.34 × 0.25 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	6479 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	5952 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.927	R_int = 0.042
36558 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.39 e Å⁻³
S = 1.01	Δρ_min = −0.24 e Å⁻³
6479 reflections	Absolute structure: Flack (1983), 2828 Friedel pairs
228 parameters	Absolute structure parameter: −0.01 (4)
0 restraints

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	0.22775 (4)	0.63689 (3)	0.139002 (14)	0.01803 (7)
S2	0.13141 (4)	0.84992 (3)	0.054416 (14)	0.01782 (7)
N1	0.19500 (13)	0.60797 (10)	0.01133 (5)	0.01500 (19)
N2	0.15503 (13)	0.65520 (9)	−0.05106 (5)	0.01352 (18)
N3	0.25257 (12)	0.79575 (9)	−0.13046 (5)	0.01259 (18)
N4	0.32207 (12)	1.01589 (9)	−0.10384 (5)	0.01291 (18)
N5	0.32568 (13)	0.93935 (9)	−0.20956 (5)	0.01266 (18)
C1	0.18653 (15)	0.68568 (11)	0.05930 (6)	0.0150 (2)
C2	0.20870 (15)	0.77788 (11)	−0.06931 (5)	0.0123 (2)
C3	0.29962 (14)	0.91713 (11)	−0.14572 (5)	0.01168 (19)
C4	0.28199 (15)	0.99345 (11)	−0.04183 (5)	0.0132 (2)
C5	0.21638 (15)	0.87583 (11)	−0.02250 (5)	0.0133 (2)
C6	0.24582 (16)	0.46325 (12)	0.13017 (6)	0.0178 (2)
H6A	0.2309	0.4225	0.1733	0.021*
H6B	0.1592	0.4320	0.1014	0.021*
C7	0.40534 (17)	0.42034 (15)	0.10245 (7)	0.0253 (3)
H7A	0.4078	0.3259	0.0995	0.038*
H7B	0.4919	0.4499	0.1309	0.038*
H7C	0.4194	0.4574	0.0590	0.038*
C8	0.13997 (14)	0.55459 (11)	−0.09830 (5)	0.0126 (2)
C9	0.04771 (15)	0.57732 (12)	−0.15373 (6)	0.0151 (2)
H9A	−0.0024	0.6587	−0.1599	0.018*
C10	0.02966 (15)	0.48028 (13)	−0.19981 (6)	0.0170 (2)
H10A	−0.0308	0.4963	−0.2381	0.020*
C11	0.09974 (15)	0.35941 (13)	−0.19027 (6)	0.0178 (2)
H11A	0.0866	0.2932	−0.2217	0.021*
C12	0.18862 (15)	0.33680 (11)	−0.13451 (6)	0.0167 (2)
H12A	0.2351	0.2543	−0.1276	0.020*
C13	0.21026 (15)	0.43426 (11)	−0.08857 (6)	0.0151 (2)
H13A	0.2727	0.4186	−0.0508	0.018*
C14	0.39636 (15)	1.05860 (11)	−0.23480 (6)	0.0137 (2)
H14A	0.4645	1.1009	−0.2017	0.016*
H14B	0.3126	1.1199	−0.2491	0.016*
C15	0.49585 (15)	1.01128 (13)	−0.29226 (6)	0.0163 (2)
H15A	0.6028	0.9815	−0.2780	0.020*
H15B	0.5087	1.0797	−0.3254	0.020*
C16	0.39505 (16)	0.89890 (12)	−0.31828 (6)	0.0163 (2)
H16A	0.3043	0.9306	−0.3447	0.020*
H16B	0.4607	0.8394	−0.3449	0.020*
C17	0.33637 (16)	0.83293 (11)	−0.25639 (6)	0.0151 (2)
H17A	0.2306	0.7921	−0.2632	0.018*
H17B	0.4132	0.7665	−0.2416	0.018*
C18	0.30455 (17)	1.10308 (12)	0.00497 (6)	0.0187 (2)
H18A	0.3845	1.1632	−0.0123	0.028*
H18B	0.3412	1.0693	0.0469	0.028*
H18C	0.2027	1.1484	0.0109	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02582 (15)	0.01779 (13)	0.01048 (11)	−0.00161 (12)	0.00034 (11)	0.00230 (10)
S2	0.02715 (16)	0.01428 (12)	0.01203 (12)	0.00202 (12)	0.00653 (11)	0.00012 (10)
N1	0.0204 (5)	0.0137 (4)	0.0109 (4)	−0.0006 (4)	0.0009 (4)	0.0031 (3)
N2	0.0203 (5)	0.0105 (4)	0.0098 (4)	−0.0011 (4)	0.0010 (3)	0.0008 (3)
N3	0.0161 (5)	0.0108 (4)	0.0109 (4)	0.0005 (3)	0.0010 (3)	0.0011 (3)
N4	0.0158 (5)	0.0110 (4)	0.0119 (4)	0.0002 (4)	0.0005 (3)	0.0002 (3)
N5	0.0181 (5)	0.0095 (4)	0.0104 (4)	0.0000 (3)	0.0019 (3)	0.0002 (3)
C1	0.0188 (5)	0.0144 (5)	0.0117 (5)	−0.0013 (4)	0.0020 (4)	0.0030 (4)
C2	0.0139 (5)	0.0110 (4)	0.0119 (5)	0.0008 (4)	0.0017 (4)	0.0005 (4)
C3	0.0125 (5)	0.0118 (4)	0.0108 (4)	0.0018 (4)	0.0006 (4)	0.0012 (4)
C4	0.0162 (5)	0.0114 (4)	0.0120 (4)	0.0012 (4)	−0.0002 (4)	−0.0005 (4)
C5	0.0176 (5)	0.0121 (5)	0.0102 (4)	0.0014 (4)	0.0021 (4)	0.0009 (4)
C6	0.0181 (6)	0.0169 (5)	0.0183 (5)	−0.0004 (4)	0.0000 (4)	0.0056 (4)
C7	0.0201 (6)	0.0296 (7)	0.0261 (7)	0.0060 (6)	−0.0007 (5)	0.0019 (5)
C8	0.0144 (5)	0.0109 (4)	0.0124 (4)	−0.0020 (4)	0.0023 (4)	−0.0006 (4)
C9	0.0160 (5)	0.0135 (5)	0.0158 (5)	−0.0003 (4)	0.0001 (4)	0.0014 (4)
C10	0.0160 (6)	0.0189 (6)	0.0162 (5)	−0.0023 (4)	−0.0012 (4)	−0.0011 (4)
C11	0.0185 (6)	0.0160 (5)	0.0189 (5)	−0.0034 (5)	0.0021 (4)	−0.0051 (4)
C12	0.0188 (5)	0.0118 (5)	0.0193 (5)	−0.0008 (4)	0.0035 (4)	−0.0003 (4)
C13	0.0170 (6)	0.0131 (5)	0.0152 (5)	0.0000 (4)	0.0013 (4)	0.0014 (4)
C14	0.0161 (5)	0.0117 (5)	0.0133 (5)	−0.0009 (4)	0.0013 (4)	0.0024 (4)
C15	0.0165 (5)	0.0202 (6)	0.0122 (5)	−0.0021 (4)	0.0011 (4)	0.0003 (4)
C16	0.0199 (6)	0.0187 (5)	0.0104 (5)	−0.0015 (5)	0.0010 (4)	0.0006 (4)
C17	0.0216 (6)	0.0115 (5)	0.0123 (5)	0.0006 (4)	0.0019 (4)	−0.0009 (4)
C18	0.0282 (7)	0.0136 (5)	0.0144 (5)	−0.0019 (5)	−0.0004 (5)	−0.0031 (4)

Geometric parameters (Å, º) top

S1—C1	1.7502 (12)	C8—C9	1.3968 (16)
S1—C6	1.8144 (13)	C9—C10	1.3901 (17)
S2—C5	1.7553 (11)	C9—H9A	0.9500
S2—C1	1.7657 (12)	C10—C11	1.3963 (19)
N1—C1	1.2757 (15)	C10—H10A	0.9500
N1—N2	1.4137 (13)	C11—C12	1.3868 (18)
N2—C2	1.3991 (14)	C11—H11A	0.9500
N2—C8	1.4307 (15)	C12—C13	1.3948 (16)
N3—C2	1.3235 (14)	C12—H12A	0.9500
N3—C3	1.3545 (14)	C13—H13A	0.9500
N4—C4	1.3394 (14)	C14—C15	1.5264 (17)
N4—C3	1.3508 (14)	C14—H14A	0.9900
N5—C3	1.3512 (14)	C14—H14B	0.9900
N5—C14	1.4646 (15)	C15—C16	1.5337 (18)
N5—C17	1.4670 (15)	C15—H15A	0.9900
C2—C5	1.4005 (15)	C15—H15B	0.9900
C4—C5	1.3942 (15)	C16—C17	1.5261 (16)
C4—C18	1.5008 (16)	C16—H16A	0.9900
C6—C7	1.5171 (19)	C16—H16B	0.9900
C6—H6A	0.9900	C17—H17A	0.9900
C6—H6B	0.9900	C17—H17B	0.9900
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800
C8—C13	1.3926 (16)

C1—S1—C6	102.06 (6)	C8—C9—H9A	120.2
C5—S2—C1	95.34 (5)	C9—C10—C11	120.48 (12)
C1—N1—N2	118.10 (10)	C9—C10—H10A	119.8
C2—N2—N1	118.84 (9)	C11—C10—H10A	119.8
C2—N2—C8	120.50 (9)	C12—C11—C10	119.50 (11)
N1—N2—C8	112.67 (9)	C12—C11—H11A	120.2
C2—N3—C3	115.51 (10)	C10—C11—H11A	120.2
C4—N4—C3	116.20 (10)	C11—C12—C13	120.52 (11)
C3—N5—C14	123.61 (10)	C11—C12—H12A	119.7
C3—N5—C17	121.36 (9)	C13—C12—H12A	119.7
C14—N5—C17	112.11 (9)	C8—C13—C12	119.73 (11)
N1—C1—S1	122.13 (9)	C8—C13—H13A	120.1
N1—C1—S2	125.35 (9)	C12—C13—H13A	120.1
S1—C1—S2	112.52 (7)	N5—C14—C15	102.92 (9)
N3—C2—N2	118.10 (10)	N5—C14—H14A	111.2
N3—C2—C5	122.66 (10)	C15—C14—H14A	111.2
N2—C2—C5	119.23 (10)	N5—C14—H14B	111.2
N4—C3—N5	117.95 (10)	C15—C14—H14B	111.2
N4—C3—N3	126.56 (10)	H14A—C14—H14B	109.1
N5—C3—N3	115.49 (10)	C14—C15—C16	102.40 (10)
N4—C4—C5	121.46 (10)	C14—C15—H15A	111.3
N4—C4—C18	116.64 (10)	C16—C15—H15A	111.3
C5—C4—C18	121.85 (10)	C14—C15—H15B	111.3
C4—C5—C2	117.07 (10)	C16—C15—H15B	111.3
C4—C5—S2	123.37 (8)	H15A—C15—H15B	109.2
C2—C5—S2	119.38 (9)	C17—C16—C15	103.02 (9)
C7—C6—S1	113.66 (10)	C17—C16—H16A	111.2
C7—C6—H6A	108.8	C15—C16—H16A	111.2
S1—C6—H6A	108.8	C17—C16—H16B	111.2
C7—C6—H6B	108.8	C15—C16—H16B	111.2
S1—C6—H6B	108.8	H16A—C16—H16B	109.1
H6A—C6—H6B	107.7	N5—C17—C16	103.36 (9)
C6—C7—H7A	109.5	N5—C17—H17A	111.1
C6—C7—H7B	109.5	C16—C17—H17A	111.1
H7A—C7—H7B	109.5	N5—C17—H17B	111.1
C6—C7—H7C	109.5	C16—C17—H17B	111.1
H7A—C7—H7C	109.5	H17A—C17—H17B	109.1
H7B—C7—H7C	109.5	C4—C18—H18A	109.5
C13—C8—C9	120.08 (11)	C4—C18—H18B	109.5
C13—C8—N2	121.16 (10)	H18A—C18—H18B	109.5
C9—C8—N2	118.72 (10)	C4—C18—H18C	109.5
C10—C9—C8	119.66 (11)	H18A—C18—H18C	109.5
C10—C9—H9A	120.2	H18B—C18—H18C	109.5

C1—N1—N2—C2	41.93 (16)	C18—C4—C5—S2	8.17 (17)
C1—N1—N2—C8	−168.98 (11)	N3—C2—C5—C4	−3.72 (18)
N2—N1—C1—S1	178.19 (9)	N2—C2—C5—C4	175.25 (11)
N2—N1—C1—S2	−1.02 (17)	N3—C2—C5—S2	171.64 (10)
C6—S1—C1—N1	−8.61 (13)	N2—C2—C5—S2	−9.38 (16)
C6—S1—C1—S2	170.70 (7)	C1—S2—C5—C4	−147.93 (11)
C5—S2—C1—N1	−33.47 (13)	C1—S2—C5—C2	37.01 (11)
C5—S2—C1—S1	147.25 (7)	C1—S1—C6—C7	78.51 (11)
C3—N3—C2—N2	178.42 (10)	C2—N2—C8—C13	127.99 (12)
C3—N3—C2—C5	−2.60 (18)	N1—N2—C8—C13	−20.53 (15)
N1—N2—C2—N3	143.21 (11)	C2—N2—C8—C9	−54.47 (15)
C8—N2—C2—N3	−3.42 (17)	N1—N2—C8—C9	157.01 (11)
N1—N2—C2—C5	−35.81 (16)	C13—C8—C9—C10	−1.54 (18)
C8—N2—C2—C5	177.56 (11)	N2—C8—C9—C10	−179.11 (11)
C4—N4—C3—N5	174.47 (11)	C8—C9—C10—C11	1.60 (19)
C4—N4—C3—N3	−5.39 (18)	C9—C10—C11—C12	−0.37 (19)
C14—N5—C3—N4	8.23 (17)	C10—C11—C12—C13	−0.94 (18)
C17—N5—C3—N4	167.32 (11)	C9—C8—C13—C12	0.25 (18)
C14—N5—C3—N3	−171.89 (10)	N2—C8—C13—C12	177.76 (11)
C17—N5—C3—N3	−12.81 (16)	C11—C12—C13—C8	1.00 (18)
C2—N3—C3—N4	7.60 (18)	C3—N5—C14—C15	144.67 (11)
C2—N3—C3—N5	−172.26 (10)	C17—N5—C14—C15	−16.12 (13)
C3—N4—C4—C5	−1.88 (17)	N5—C14—C15—C16	34.32 (12)
C3—N4—C4—C18	−179.27 (11)	C14—C15—C16—C17	−40.28 (12)
N4—C4—C5—C2	6.08 (18)	C3—N5—C17—C16	−170.29 (11)
C18—C4—C5—C2	−176.66 (12)	C14—N5—C17—C16	−9.01 (13)
N4—C4—C5—S2	−169.08 (9)	C15—C16—C17—N5	30.31 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N4ⁱ	0.95	2.62	3.5630 (15)	172
C15—H15B···S2ⁱⁱ	0.99	2.83	3.6264 (13)	138

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₅S₂
M_r	371.52
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.3601 (2), 10.3596 (3), 20.5754 (6)
V (Å³)	1781.98 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.43 × 0.34 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.878, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	36558, 6479, 5952
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.076, 1.01
No. of reflections	6479
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.24
Absolute structure	Flack (1983), 2828 Friedel pairs
Absolute structure parameter	−0.01 (4)

Computer programs: APEX2 (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N4ⁱ	0.95	2.62	3.5630 (15)	172
C15—H15B···S2ⁱⁱ	0.99	2.83	3.6264 (13)	138

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

Acknowledgements

The authors acknowledge Islamic Azad University, Ahvaz Branch, for financial support.

References

Bakavoli, M., Nikpour, M. & Rahimizadeh, M. (2006). Phosphorus Sulfur Silicon Relat. Elem., 180, 2265–2268. Web of Science CrossRef Google Scholar
Bakavoli, M., Nikpour, M. & Rahimizadeh, M. (2007). J. Heterocycl. Chem. 44, 463–465. Google Scholar
Bakavoli, M., Rahimizadeh, M., Shiri, A., Eshghi, H. & Nikpour, M. (2008). Heterocycles. In the press. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Elliott, A. J. (1981). J. Heterocycl. Chem. 18, 799–800. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rahimizadeh, M., Heravi, M. M. & Malekan, A. (1997). Indian J. Heterocycl. Chem. 6, 223–224. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1491

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

3-Ethyl­sulfanyl-5-methyl-1-phenyl-7-(pyrrolidin-1-yl)-1H-pyrimido[4,5-e][1,3,4]thia­diazine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Ethylsulfanyl-5-methyl-1-phenyl-7-(pyrrolidin-1-yl)-1H-pyrimido[4,5-e][1,3,4]thiadiazine