3-Benzyl-1-butyl­imidazo[1,2-a]benzo­thieno[3,2-d]pyrimidine-2,5(1H,3H)-dione

Cao, M.-H.; Zhu, J.; Ni, D.-J.

doi:10.1107/S1600536807061521

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o10

https://doi.org/10.1107/S1600536807061521

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3-Benzyl-1-butylimidazo[1,2-a]benzothieno[3,2-d]pyrimidine-2,5(1H,3H)-dione

Min-Hui Cao,^a Jun Zhu ^b and De-Jiang Ni ^c ^*

^aCollege of Science, HuaZhong Agricultural University, Wuhan 430070, People's Republic of China, ^bDepartment of Biochemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^cCollege of Horticulture and Forestry Science, HuaZhong Agricultural University, Wuhan 430070, People's Republic of China
^*Correspondence e-mail: nidejiang1021@yahoo.com.cn

(Received 19 November 2007; accepted 21 November 2007; online 6 December 2007)

In the crystal structure of the title compound, C₂₃H₂₁N₃O₂S, all ring atoms of the imidazo[1,2-a]benzothieno[3,2-d]pyrimidine system are essentially coplanar and the phenyl ring is twisted with respect to it [dihedral angle = 72.60 (9)°]. The crystal packing is mainly governed by C—H⋯π hydrogen bonds and intermolecular π–π interactions, with interplanar distances of 3.54 (1) and 3.56 (1) Å, and with distances between adjacent ring centroids of 3.72 (1) and 3.80 (1) Å. The three terminal C atoms of the butyl group are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

Related preparation and biological activity is described by Walter (1999a ,b ). For related literature, see: Ding et al. (2004 ); Janiak (2000 ). For the crystal structures of other fused pyrimidinone derivatives, see: Cao et al. (2006 ); Xu et al. (2005 ).

Experimental

Crystal data

C₂₃H₂₁N₃O₂S
M_r = 403.49
Monoclinic, P 2₁ /n
a = 13.1732 (16) Å
b = 8.4957 (11) Å
c = 18.584 (2) Å
β = 103.345 (2)°
V = 2023.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 298 (2) K
0.26 × 0.16 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.954, T_max = 0.982
15534 measured reflections
3958 independent reflections
2896 reflections with I > 2σ(I)
R_int = 0.129

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.170
S = 1.00
3958 reflections
292 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg5ⁱ	0.96	2.81	3.682 (3)	156
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807061521/at2501sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061521/at2501Isup2.hkl

checkCIF report

Comment top

In the field of bioactive molecules, thienopyrimidine have received a great deal of attention (Walter, 1999a,b). Recently, There have being focused on the synthesis of the fused heterocycle systems containing thienopyrimidine via aza-Wittig reaction at room temperature(Ding et al., 2004). Herein, we present X-ray crystallographic analysis of the compound (I) in this paper, (Fig. 1), which may be used as a new precursor for obtaining bioactive molecules.

In the molecule, the bond lengths and angles are unexceptional (Cao et al., 2006; Xu et al., 2005). The four fused rings are close to coplanarity, with maximum deviations 0.060 (2)Å and -0.033 (3)Å for O3 and C11, respectively, which forms a dihedral angle of 72.60 (9)° with the adjacent C18—C23 phenyl ring.

Intermolecular C—H···π hydrogen bonds (Table 2) seem to be effective in stabilizing the crystal structure. Further stability the crystal structure is provided by offset π-π stacking interactions (Janiak, 2000) involving the thiophene (A), the imidazoe (B) and the C1—C6 benzene (C) rings. The A:C interplanar distance is 3.54 (1) Å with distances between adjacent ring centroids of 3.72 (1)Å (symmetry code relating the adjacent rings: 1 - x, 2 - y, -z). A further interaction occurs between B adjacent C rings (symmetry code: 1 - x, 1 - y, -z), with an interplanar distance of 3.56 (1)Å and a centroid-to-centroid distance of 3.80 (1)Å (Fig. 2).

Related literature top

Related preparation and biological activity is described by Walter (1999a,b). For related literature, see: Ding et al. (2004); Janiak (2000). For the crystal structures of other fused pyrimidinone derivatives, see: Cao et al. (2006); Xu et al. (2005).

Experimental top

To a solution of the ethyl 3-((butylimino)methyleneamino)benzothiophene-2-carboxylate (3 mmol) in dichloromethane (5 ml) was added ethyl 2-amino-3-phenylpropanoate (3 mmol). After stirring the reaction mixture for 2 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 5 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 86%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:3 v/v) at room temperature.

Structure description top

Related preparation and biological activity is described by Walter (1999a,b). For related literature, see: Ding et al. (2004); Janiak (2000). For the crystal structures of other fused pyrimidinone derivatives, see: Cao et al. (2006); Xu et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Only the major disorder component is shown.
	Fig. 2. The packing of the title compound.

3-Benzyl-1-butylimidazo[1,2-a]benzothieno[3,2-d]pyrimidine- 2,5(1H,3H)-dione top

Crystal data top

C₂₃H₂₁N₃O₂S	F(000) = 848
M_r = 403.49	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3589 reflections
a = 13.1732 (16) Å	θ = 2.3–23.5°
b = 8.4957 (11) Å	µ = 0.18 mm⁻¹
c = 18.584 (2) Å	T = 298 K
β = 103.345 (2)°	Prism, colourless
V = 2023.7 (4) Å³	0.26 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area0detector diffractometer	3958 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.129
φ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
T_min = 0.954, T_max = 0.982	k = −10→10
15534 measured reflections	l = −22→22

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0962P)²] where P = (F_o² + 2F_c²)/3
3958 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.26 e Å⁻³
22 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₃H₂₁N₃O₂S	V = 2023.7 (4) Å³
M_r = 403.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1732 (16) Å	µ = 0.18 mm⁻¹
b = 8.4957 (11) Å	T = 298 K
c = 18.584 (2) Å	0.26 × 0.16 × 0.10 mm
β = 103.345 (2)°

Data collection top

Bruker SMART 4K CCD area0detector diffractometer	3958 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2896 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.982	R_int = 0.129
15534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	22 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
3958 reflections	Δρ_min = −0.32 e Å⁻³
292 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	Occ. (<1)
C1	0.45304 (17)	0.7981 (3)	0.00701 (13)	0.0455 (6)
C2	0.40479 (19)	0.8227 (3)	−0.06750 (13)	0.0541 (6)
H2	0.4330	0.7798	−0.1046	0.065*
C3	0.31509 (19)	0.9112 (3)	−0.08510 (14)	0.0613 (7)
H3	0.2828	0.9287	−0.1345	0.074*
C4	0.27219 (19)	0.9745 (3)	−0.03029 (15)	0.0658 (8)
H4	0.2111	1.0332	−0.0435	0.079*
C5	0.31784 (19)	0.9528 (3)	0.04333 (15)	0.0605 (7)
H5	0.2883	0.9956	0.0798	0.073*
C6	0.40899 (17)	0.8655 (3)	0.06174 (13)	0.0500 (6)
C7	0.54724 (16)	0.7149 (3)	0.03847 (12)	0.0441 (5)
C8	0.57103 (17)	0.7199 (3)	0.11501 (12)	0.0465 (6)
C9	0.66293 (18)	0.6487 (3)	0.15852 (12)	0.0497 (6)
C10	0.68847 (18)	0.5729 (3)	0.03767 (12)	0.0454 (5)
C11	0.8372 (2)	0.4266 (3)	0.06606 (15)	0.0563 (6)
C12	0.81459 (18)	0.4798 (3)	0.13877 (14)	0.0544 (6)
H12	0.7970	0.3870	0.1648	0.065*
C13	0.7543 (2)	0.4725 (3)	−0.06900 (13)	0.0638 (7)
H13A	0.6849	0.4359	−0.0928	0.077*	0.613 (9)
H13B	0.8029	0.3908	−0.0754	0.077*	0.613 (9)
H13C	0.6838	0.4415	−0.0932	0.077*	0.387 (9)
H13D	0.8002	0.3872	−0.0756	0.077*	0.387 (9)
C14	0.8106 (7)	0.6116 (9)	−0.0933 (4)	0.062 (2)	0.613 (9)
H14A	0.8832	0.6084	−0.0668	0.074*	0.613 (9)
H14B	0.7807	0.7079	−0.0793	0.074*	0.613 (9)
C15	0.8060 (5)	0.6175 (9)	−0.1761 (3)	0.087 (2)	0.613 (9)
H15A	0.8560	0.6945	−0.1852	0.105*	0.613 (9)
H15B	0.8260	0.5156	−0.1920	0.105*	0.613 (9)
C16	0.7009 (7)	0.6589 (14)	−0.2207 (5)	0.154 (4)	0.613 (9)
H16A	0.6520	0.5788	−0.2150	0.230*	0.613 (9)
H16B	0.7031	0.6667	−0.2719	0.230*	0.613 (9)
H16C	0.6797	0.7580	−0.2042	0.230*	0.613 (9)
C14'	0.7768 (13)	0.6158 (15)	−0.1097 (5)	0.076 (4)	0.387 (9)
H14C	0.8496	0.6457	−0.0940	0.091*	0.387 (9)
H14D	0.7337	0.7037	−0.1018	0.091*	0.387 (9)
C15'	0.7494 (10)	0.5634 (13)	−0.1926 (4)	0.101 (4)	0.387 (9)
H15C	0.7920	0.4746	−0.2002	0.121*	0.387 (9)
H15D	0.6765	0.5343	−0.2083	0.121*	0.387 (9)
C16'	0.7727 (11)	0.7057 (14)	−0.2344 (5)	0.117 (4)	0.387 (9)
H16D	0.7340	0.7943	−0.2230	0.175*	0.387 (9)
H16E	0.7528	0.6849	−0.2866	0.175*	0.387 (9)
H16F	0.8460	0.7285	−0.2204	0.175*	0.387 (9)
C17	0.90741 (18)	0.5630 (3)	0.18900 (13)	0.0555 (7)
H17A	0.8906	0.5818	0.2364	0.067*
H17B	0.9667	0.4920	0.1975	0.067*
C18	0.93996 (16)	0.7166 (3)	0.16112 (12)	0.0475 (6)
C19	0.99200 (17)	0.7229 (3)	0.10411 (13)	0.0509 (6)
H19	1.0040	0.6301	0.0808	0.061*
C20	1.02611 (18)	0.8632 (3)	0.08140 (14)	0.0543 (6)
H20	1.0604	0.8644	0.0429	0.065*
C21	1.00975 (19)	1.0019 (3)	0.11538 (14)	0.0593 (7)
H21	1.0336	1.0966	0.1004	0.071*
C22	0.9581 (2)	0.9992 (3)	0.17149 (15)	0.0643 (7)
H22	0.9465	1.0925	0.1945	0.077*
C23	0.92311 (19)	0.8578 (3)	0.19387 (13)	0.0575 (7)
H23	0.8876	0.8575	0.2317	0.069*
N1	0.60676 (14)	0.6380 (2)	−0.00223 (10)	0.0468 (5)
N2	0.75950 (15)	0.4872 (2)	0.01036 (11)	0.0521 (5)
N3	0.72009 (13)	0.5741 (2)	0.11365 (9)	0.0476 (5)
O1	0.69271 (13)	0.6488 (2)	0.22618 (9)	0.0653 (5)
O2	0.91073 (15)	0.3495 (2)	0.05804 (11)	0.0710 (6)
S1	0.48079 (5)	0.82378 (9)	0.15079 (3)	0.0585 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0434 (12)	0.0490 (14)	0.0430 (12)	−0.0121 (10)	0.0076 (10)	−0.0026 (10)
C2	0.0530 (14)	0.0616 (16)	0.0450 (13)	−0.0097 (12)	0.0054 (11)	−0.0037 (11)
C3	0.0555 (15)	0.0682 (18)	0.0539 (14)	−0.0071 (13)	−0.0001 (12)	0.0033 (13)
C4	0.0513 (15)	0.0627 (18)	0.0779 (19)	0.0005 (13)	0.0037 (14)	−0.0013 (15)
C5	0.0517 (14)	0.0638 (17)	0.0666 (16)	−0.0008 (12)	0.0149 (12)	−0.0094 (13)
C6	0.0454 (13)	0.0577 (15)	0.0463 (13)	−0.0114 (11)	0.0093 (11)	−0.0051 (11)
C7	0.0422 (12)	0.0504 (14)	0.0396 (11)	−0.0098 (10)	0.0092 (10)	−0.0035 (10)
C8	0.0448 (12)	0.0572 (15)	0.0391 (12)	−0.0085 (11)	0.0132 (10)	−0.0015 (10)
C9	0.0477 (13)	0.0636 (16)	0.0390 (12)	−0.0122 (11)	0.0124 (10)	0.0058 (11)
C10	0.0520 (13)	0.0441 (13)	0.0422 (12)	−0.0078 (11)	0.0150 (11)	−0.0013 (10)
C11	0.0602 (15)	0.0419 (14)	0.0678 (16)	−0.0027 (12)	0.0170 (13)	0.0062 (12)
C12	0.0559 (14)	0.0524 (15)	0.0562 (14)	−0.0005 (11)	0.0154 (12)	0.0185 (12)
C13	0.0673 (16)	0.0719 (19)	0.0535 (15)	0.0011 (14)	0.0163 (13)	−0.0162 (14)
C14	0.079 (5)	0.065 (4)	0.041 (3)	0.019 (3)	0.013 (3)	0.008 (3)
C15	0.101 (5)	0.110 (5)	0.047 (3)	−0.012 (4)	0.010 (3)	0.005 (3)
C16	0.141 (7)	0.175 (8)	0.118 (6)	−0.013 (6)	−0.023 (5)	0.032 (5)
C14'	0.096 (11)	0.095 (8)	0.037 (5)	0.030 (6)	0.014 (6)	0.017 (5)
C15'	0.074 (8)	0.147 (12)	0.077 (7)	−0.010 (7)	0.005 (6)	−0.006 (7)
C16'	0.137 (8)	0.130 (8)	0.089 (6)	−0.019 (6)	0.037 (6)	0.030 (6)
C17	0.0504 (13)	0.0694 (18)	0.0454 (13)	0.0088 (12)	0.0080 (11)	0.0162 (12)
C18	0.0373 (11)	0.0619 (16)	0.0397 (12)	0.0052 (11)	0.0017 (10)	0.0068 (11)
C19	0.0527 (13)	0.0534 (15)	0.0484 (13)	0.0044 (11)	0.0151 (11)	−0.0039 (11)
C20	0.0549 (14)	0.0576 (17)	0.0543 (14)	0.0015 (12)	0.0208 (12)	0.0027 (12)
C21	0.0570 (14)	0.0509 (15)	0.0690 (17)	−0.0023 (12)	0.0125 (13)	0.0031 (13)
C22	0.0655 (16)	0.0589 (18)	0.0679 (17)	0.0055 (14)	0.0138 (14)	−0.0143 (14)
C23	0.0510 (14)	0.077 (2)	0.0451 (13)	0.0078 (13)	0.0125 (11)	−0.0049 (13)
N1	0.0472 (11)	0.0540 (12)	0.0394 (10)	−0.0041 (9)	0.0104 (9)	−0.0025 (9)
N2	0.0554 (11)	0.0516 (12)	0.0513 (11)	0.0024 (9)	0.0163 (10)	−0.0016 (9)
N3	0.0447 (10)	0.0579 (13)	0.0406 (10)	−0.0026 (9)	0.0106 (9)	0.0074 (9)
O1	0.0580 (10)	0.1020 (15)	0.0363 (9)	−0.0023 (10)	0.0116 (8)	0.0123 (9)
O2	0.0705 (12)	0.0522 (11)	0.0911 (14)	0.0144 (9)	0.0202 (11)	−0.0008 (10)
S1	0.0510 (4)	0.0854 (6)	0.0405 (4)	−0.0052 (3)	0.0131 (3)	−0.0096 (3)

Geometric parameters (Å, º) top

C1—C2	1.400 (3)	C13—H13D	0.9700
C1—C6	1.404 (3)	C14—C15	1.527 (7)
C1—C7	1.431 (3)	C14—H14A	0.9700
C2—C3	1.375 (4)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.482 (8)
C3—C4	1.383 (4)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.374 (3)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.385 (3)	C16—H16C	0.9600
C5—H5	0.9300	C14'—C15'	1.564 (9)
C6—S1	1.743 (2)	C14'—H14C	0.9700
C7—N1	1.373 (3)	C14'—H14D	0.9700
C7—C8	1.385 (3)	C15'—C16'	1.506 (9)
C8—C9	1.426 (3)	C15'—H15C	0.9700
C8—S1	1.732 (2)	C15'—H15D	0.9700
C9—O1	1.228 (3)	C16'—H16D	0.9600
C9—N3	1.398 (3)	C16'—H16E	0.9600
C10—N1	1.283 (3)	C16'—H16F	0.9600
C10—N2	1.372 (3)	C17—C18	1.503 (3)
C10—N3	1.377 (3)	C17—H17A	0.9700
C11—O2	1.207 (3)	C17—H17B	0.9700
C11—N2	1.377 (3)	C18—C23	1.386 (3)
C11—C12	1.518 (4)	C18—C19	1.389 (3)
C12—N3	1.463 (3)	C19—C20	1.374 (3)
C12—C17	1.529 (3)	C19—H19	0.9300
C12—H12	0.9800	C20—C21	1.377 (3)
C13—N2	1.466 (3)	C20—H20	0.9300
C13—C14'	1.498 (9)	C21—C22	1.371 (4)
C13—C14	1.519 (7)	C21—H21	0.9300
C13—H13A	0.9700	C22—C23	1.385 (4)
C13—H13B	0.9700	C22—H22	0.9300
C13—H13C	0.9700	C23—H23	0.9300

C2—C1—C6	119.1 (2)	C13—C14—H14A	108.6
C2—C1—C7	129.1 (2)	C15—C14—H14A	108.6
C6—C1—C7	111.7 (2)	C13—C14—H14B	108.6
C3—C2—C1	119.1 (2)	C15—C14—H14B	108.6
C3—C2—H2	120.5	H14A—C14—H14B	107.6
C1—C2—H2	120.5	C16—C15—C14	112.8 (6)
C2—C3—C4	120.8 (2)	C16—C15—H15A	109.0
C2—C3—H3	119.6	C14—C15—H15A	109.0
C4—C3—H3	119.6	C16—C15—H15B	109.0
C5—C4—C3	121.5 (2)	C14—C15—H15B	109.0
C5—C4—H4	119.3	H15A—C15—H15B	107.8
C3—C4—H4	119.3	C15—C16—H16A	109.5
C4—C5—C6	118.2 (2)	C15—C16—H16B	109.5
C4—C5—H5	120.9	H16A—C16—H16B	109.5
C6—C5—H5	120.9	C15—C16—H16C	109.5
C5—C6—C1	121.3 (2)	H16A—C16—H16C	109.5
C5—C6—S1	126.4 (2)	H16B—C16—H16C	109.5
C1—C6—S1	112.37 (18)	C13—C14'—C15'	103.8 (7)
N1—C7—C8	123.9 (2)	C13—C14'—H14C	111.0
N1—C7—C1	124.2 (2)	C15'—C14'—H14C	111.0
C8—C7—C1	111.9 (2)	C13—C14'—H14D	111.0
C7—C8—C9	122.0 (2)	C15'—C14'—H14D	111.0
C7—C8—S1	113.44 (18)	H14C—C14'—H14D	109.0
C9—C8—S1	124.51 (17)	C16'—C15'—C14'	104.6 (7)
O1—C9—N3	121.5 (2)	C16'—C15'—H15C	110.8
O1—C9—C8	127.5 (2)	C14'—C15'—H15C	110.8
N3—C9—C8	110.96 (19)	C16'—C15'—H15D	110.8
N1—C10—N2	124.6 (2)	C14'—C15'—H15D	110.8
N1—C10—N3	127.2 (2)	H15C—C15'—H15D	108.9
N2—C10—N3	108.2 (2)	C18—C17—C12	116.25 (18)
O2—C11—N2	126.1 (3)	C18—C17—H17A	108.2
O2—C11—C12	126.8 (2)	C12—C17—H17A	108.2
N2—C11—C12	107.1 (2)	C18—C17—H17B	108.2
N3—C12—C11	101.91 (19)	C12—C17—H17B	108.2
N3—C12—C17	116.3 (2)	H17A—C17—H17B	107.4
C11—C12—C17	112.8 (2)	C23—C18—C19	117.3 (2)
N3—C12—H12	108.5	C23—C18—C17	120.9 (2)
C11—C12—H12	108.5	C19—C18—C17	121.8 (2)
C17—C12—H12	108.5	C20—C19—C18	121.4 (2)
N2—C13—C14'	118.0 (5)	C20—C19—H19	119.3
N2—C13—C14	108.7 (3)	C18—C19—H19	119.3
C14'—C13—C14	18.3 (7)	C19—C20—C21	120.3 (2)
N2—C13—H13A	107.8	C19—C20—H20	119.9
C14'—C13—H13A	107.8	C21—C20—H20	119.9
C14—C13—H13A	126.0	C22—C21—C20	119.5 (3)
N2—C13—H13B	107.8	C22—C21—H21	120.2
C14'—C13—H13B	107.8	C20—C21—H21	120.2
C14—C13—H13B	97.9	C21—C22—C23	120.0 (2)
H13A—C13—H13B	107.1	C21—C22—H22	120.0
N2—C13—H13C	107.9	C23—C22—H22	120.0
C14'—C13—H13C	105.5	C18—C23—C22	121.4 (2)
C14—C13—H13C	123.7	C18—C23—H23	119.3
H13A—C13—H13C	2.9	C22—C23—H23	119.3
H13B—C13—H13C	109.7	C10—N1—C7	113.33 (18)
N2—C13—H13D	107.8	C10—N2—C11	111.9 (2)
C14'—C13—H13D	109.9	C10—N2—C13	122.7 (2)
C14—C13—H13D	100.5	C11—N2—C13	125.4 (2)
H13A—C13—H13D	104.6	C10—N3—C9	122.56 (19)
H13B—C13—H13D	2.8	C10—N3—C12	110.89 (19)
H13C—C13—H13D	107.2	C9—N3—C12	126.42 (18)
C13—C14—C15	114.6 (6)	C8—S1—C6	90.52 (11)

C6—C1—C2—C3	−0.5 (3)	C18—C19—C20—C21	0.4 (4)
C7—C1—C2—C3	−178.2 (2)	C19—C20—C21—C22	−0.8 (4)
C1—C2—C3—C4	−0.4 (4)	C20—C21—C22—C23	0.3 (4)
C2—C3—C4—C5	0.6 (4)	C19—C18—C23—C22	−1.0 (3)
C3—C4—C5—C6	0.2 (4)	C17—C18—C23—C22	176.2 (2)
C4—C5—C6—C1	−1.2 (4)	C21—C22—C23—C18	0.6 (4)
C4—C5—C6—S1	179.5 (2)	N2—C10—N1—C7	178.9 (2)
C2—C1—C6—C5	1.3 (3)	N3—C10—N1—C7	−0.4 (3)
C7—C1—C6—C5	179.4 (2)	C8—C7—N1—C10	−1.2 (3)
C2—C1—C6—S1	−179.29 (18)	C1—C7—N1—C10	179.3 (2)
C7—C1—C6—S1	−1.2 (2)	N1—C10—N2—C11	−177.8 (2)
C2—C1—C7—N1	−2.0 (4)	N3—C10—N2—C11	1.6 (3)
C6—C1—C7—N1	−179.8 (2)	N1—C10—N2—C13	5.6 (4)
C2—C1—C7—C8	178.4 (2)	N3—C10—N2—C13	−174.9 (2)
C6—C1—C7—C8	0.6 (3)	O2—C11—N2—C10	−178.5 (2)
N1—C7—C8—C9	2.1 (4)	C12—C11—N2—C10	−0.3 (3)
C1—C7—C8—C9	−178.3 (2)	O2—C11—N2—C13	−2.0 (4)
N1—C7—C8—S1	−179.33 (17)	C12—C11—N2—C13	176.1 (2)
C1—C7—C8—S1	0.3 (3)	C14'—C13—N2—C10	69.0 (8)
C7—C8—C9—O1	178.4 (2)	C14—C13—N2—C10	86.1 (5)
S1—C8—C9—O1	0.0 (4)	C14'—C13—N2—C11	−107.1 (8)
C7—C8—C9—N3	−1.4 (3)	C14—C13—N2—C11	−90.0 (5)
S1—C8—C9—N3	−179.76 (16)	N1—C10—N3—C9	1.0 (4)
O2—C11—C12—N3	177.1 (2)	N2—C10—N3—C9	−178.42 (19)
N2—C11—C12—N3	−1.0 (2)	N1—C10—N3—C12	177.1 (2)
O2—C11—C12—C17	51.7 (3)	N2—C10—N3—C12	−2.3 (2)
N2—C11—C12—C17	−126.5 (2)	O1—C9—N3—C10	−179.8 (2)
N2—C13—C14—C15	−176.5 (5)	C8—C9—N3—C10	0.0 (3)
C14'—C13—C14—C15	−53 (2)	O1—C9—N3—C12	4.7 (4)
C13—C14—C15—C16	71.4 (10)	C8—C9—N3—C12	−175.5 (2)
N2—C13—C14'—C15'	−172.5 (7)	C11—C12—N3—C10	2.0 (2)
C14—C13—C14'—C15'	124 (3)	C17—C12—N3—C10	125.1 (2)
C13—C14'—C15'—C16'	−179.4 (12)	C11—C12—N3—C9	177.9 (2)
N3—C12—C17—C18	−52.3 (3)	C17—C12—N3—C9	−59.0 (3)
C11—C12—C17—C18	65.0 (3)	C7—C8—S1—C6	−0.82 (19)
C12—C17—C18—C23	109.3 (3)	C9—C8—S1—C6	177.7 (2)
C12—C17—C18—C19	−73.6 (3)	C5—C6—S1—C8	−179.5 (2)
C23—C18—C19—C20	0.5 (3)	C1—C6—S1—C8	1.17 (18)
C17—C18—C19—C20	−176.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg5ⁱ	0.96	2.81	3.682 (3)	156

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁N₃O₂S
M_r	403.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.1732 (16), 8.4957 (11), 18.584 (2)
β (°)	103.345 (2)
V (Å³)	2023.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.26 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area0detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.954, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	15534, 3958, 2896
R_int	0.129
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.170, 1.00
No. of reflections	3958
No. of parameters	292
No. of restraints	22
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg5ⁱ	0.96	2.81	3.682 (3)	156

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (project No. 20102001).

References

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