3-Butyl-2-propyl­amino-1-benzo­thieno[3,2-d]pyrimidin-4(3H)-one

Xu, S.

doi:10.1107/S1600536807062484

organic compounds

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Volume 64| Part 1| January 2008| Page o42

https://doi.org/10.1107/S1600536807062484

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3-Butyl-2-propylamino-1-benzothieno[3,2-d]pyrimidin-4(3H)-one

Shengzhen Xu ^a ^*

^aCollege of Basic Science, Huazhong Agricultural University, Wuhan 430070, People's Republic of China
^*Correspondence e-mail: xsz1976@yahoo.com.cn

(Received 22 November 2007; accepted 23 November 2007; online 6 December 2007)

In the title compound, C₁₇H₂₁N₃OS, the propyl and butyl groups are disordered over two positions; site occupation factors are 0.304 (10) and 0.696 (10). The three fused rings are coplanar. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules. Further stability is provided by offset π–π stacking interactions. Adjacent thienophene–pyrimidine and pyrimidine–benzene rings have centroid–centroid distances of 3.96 (1) and 3.55 (2) Å, respectively.

Related literature

For general background, see: Chambhare et al. (2003 ); Janiak (2000 ). For related literature, see: Ding et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₂₁N₃OS
M_r = 315.43
Monoclinic, P 2₁ /c
a = 11.4322 (6) Å
b = 14.2791 (8) Å
c = 11.6704 (6) Å
β = 116.606 (1)°
V = 1703.36 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
15640 measured reflections
3712 independent reflections
2599 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.175
S = 1.04
3712 reflections
279 parameters
23 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1ⁱ	0.97	2.52	3.478 (9)	171
N3—H3A⋯O1ⁱ	0.86	2.46	3.140 (6)	137
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062484/hk2396sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062484/hk2396Isup2.hkl

checkCIF report

Comment top

Thienopyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and anti inflammatory activities (Chambhare et al., 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing thienopyrimidine via aza-Wittig reactions at room temperature (Ding et al., 2004). We report herein the structure of one such thienopyrimidine derivative, the title compound, (I).

In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987). When the crystal structure was solved, propyl and butyl groups were found to be disordered.

Rings A (C1—C6), B (S1/C1/C6—C8) and C (N1/N2/C7—C10) are, of course, planar. The three fused rings A, B and C are also co-planar. The maximum deviation from the benzo[4,5]thieno[3,2-e]-pyrimidinone mean plane is 0.027 (3) Å (for atom C7).

In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. Further stability is provided by offset π-π stacking interactions (Janiak, 2000). The adjacent B, C and A, C rings have centroid-centroid distances of 3.96 (1) %A and 3.55 (2) %A, respectively, [symmetry code: -x, -y, 2 - z].

Related literature top

For general background, see: Chambhare et al. (2003); Janiak (2000). For related literature, see: Ding et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized according to a literature method (Ding et al., 2004). The product was recrystallized from ethanol/dichloromethane (1:2 v/v) at room temperature to give crystals suitable for single-crystal X-ray analysis.

Structure description top

For general background, see: Chambhare et al. (2003); Janiak (2000). For related literature, see: Ding et al. (2004). For bond-length data, see: Allen et al. (1987).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

3-Butyl-2-propylamino-1-benzothieno[2,3-d]pyrimidin-4(3H)-one top

Crystal data top

C₁₇H₂₁N₃OS	F(000) = 672
M_r = 315.43	D_x = 1.230 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4476 reflections
a = 11.4322 (6) Å	θ = 2.4–24.2°
b = 14.2791 (8) Å	µ = 0.20 mm⁻¹
c = 11.6704 (6) Å	T = 298 K
β = 116.606 (1)°	Block, colorless
V = 1703.36 (16) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2599 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 27.0°, θ_min = 2.0°
φ and ω scans	h = −14→14
15640 measured reflections	k = −17→18
3712 independent reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.107P)²] where P = (F_o² + 2F_c²)/3
3712 reflections	(Δ/σ)_max = 0.004
279 parameters	Δρ_max = 0.35 e Å⁻³
23 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₂₁N₃OS	V = 1703.36 (16) Å³
M_r = 315.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4322 (6) Å	µ = 0.20 mm⁻¹
b = 14.2791 (8) Å	T = 298 K
c = 11.6704 (6) Å	0.30 × 0.20 × 0.20 mm
β = 116.606 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2599 reflections with I > 2σ(I)
15640 measured reflections	R_int = 0.054
3712 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	23 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
3712 reflections	Δρ_min = −0.16 e Å⁻³
279 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)
S1	0.13711 (6)	0.04643 (4)	1.26890 (6)	0.0767 (3)
O1	0.22957 (17)	0.23409 (10)	1.18589 (13)	0.0782 (5)
N1	0.21439 (19)	−0.00118 (12)	0.97855 (15)	0.0679 (5)
N2	0.25553 (18)	0.16172 (11)	1.02369 (15)	0.0646 (5)
N3	0.2992 (7)	0.0903 (4)	0.8663 (6)	0.0835 (17)	0.696 (10)
H3A	0.3215	0.1450	0.8524	0.100*	0.696 (10)
N3'	0.2371 (11)	0.0885 (9)	0.8333 (9)	0.057 (2)	0.304 (10)
H3'	0.2257	0.1427	0.7977	0.068*	0.304 (10)
C1	0.14037 (18)	−0.08829 (14)	1.11773 (18)	0.0588 (5)
C2	0.1241 (2)	−0.17839 (15)	1.0674 (2)	0.0775 (6)
H2	0.1433	−0.1913	0.9995	0.093*
C3	0.0795 (3)	−0.24799 (17)	1.1191 (3)	0.0921 (8)
H3	0.0683	−0.3082	1.0855	0.110*
C4	0.0510 (3)	−0.2299 (2)	1.2203 (3)	0.0969 (8)
H4	0.0207	−0.2780	1.2539	0.116*
C5	0.0668 (3)	−0.14217 (19)	1.2713 (3)	0.0897 (7)
H5	0.0479	−0.1303	1.3396	0.108*
C6	0.1117 (2)	−0.07033 (16)	1.2202 (2)	0.0663 (5)
C7	0.18358 (19)	−0.00435 (13)	1.07820 (16)	0.0550 (5)
C8	0.1850 (2)	0.07176 (14)	1.15013 (17)	0.0569 (5)
C9	0.2227 (2)	0.16126 (14)	1.12618 (17)	0.0585 (5)
C10	0.2479 (2)	0.08120 (15)	0.95393 (19)	0.0708 (6)
C11	0.3166 (9)	0.0091 (5)	0.7964 (8)	0.115 (3)	0.696 (10)
H11	0.3261	−0.0490	0.8446	0.138*	0.696 (10)
C11'	0.2443 (15)	0.0099 (9)	0.7669 (9)	0.085 (5)	0.304 (10)
H11'	0.1795	−0.0319	0.7733	0.102*	0.304 (10)
C12	0.4388 (5)	0.0288 (5)	0.7817 (5)	0.118 (2)	0.696 (10)
H12A	0.4292	0.0873	0.7377	0.177*	0.696 (10)
H12B	0.4525	−0.0206	0.7332	0.177*	0.696 (10)
H12C	0.5125	0.0324	0.8648	0.177*	0.696 (10)
C12'	0.3646 (15)	−0.0512 (13)	0.8141 (10)	0.149 (9)	0.304 (10)
H12D	0.4229	−0.0277	0.7820	0.223*	0.304 (10)
H12E	0.3395	−0.1142	0.7843	0.223*	0.304 (10)
H12F	0.4080	−0.0507	0.9061	0.223*	0.304 (10)
C13	0.1988 (6)	0.0047 (7)	0.6697 (10)	0.139 (4)	0.696 (10)
H13A	0.1233	−0.0101	0.6821	0.208*	0.696 (10)
H13B	0.2109	−0.0429	0.6179	0.208*	0.696 (10)
H13C	0.1862	0.0641	0.6274	0.208*	0.696 (10)
C13'	0.1899 (19)	0.0248 (14)	0.6251 (10)	0.128 (8)	0.304 (10)
H13D	0.1081	0.0574	0.5945	0.193*	0.304 (10)
H13E	0.1764	−0.0348	0.5829	0.193*	0.304 (10)
H13F	0.2504	0.0611	0.6072	0.193*	0.304 (10)
C14	0.3278 (9)	0.2503 (6)	1.0136 (9)	0.079 (3)	0.622 (11)
H14A	0.3095	0.2584	0.9247	0.095*	0.622 (11)
H14B	0.2914	0.3040	1.0374	0.095*	0.622 (11)
C14'	0.2809 (11)	0.2515 (8)	0.9807 (12)	0.055 (2)	0.378 (11)
H14C	0.2538	0.3028	1.0179	0.066*	0.378 (11)
H14D	0.2356	0.2564	0.8881	0.066*	0.378 (11)
C15	0.4741 (8)	0.2515 (6)	1.0939 (8)	0.128 (3)	0.622 (11)
H15A	0.5120	0.1976	1.0725	0.154*	0.622 (11)
H15B	0.4941	0.2468	1.1838	0.154*	0.622 (11)
C15'	0.4291 (10)	0.2516 (6)	1.0287 (12)	0.082 (3)	0.378 (11)
H15C	0.4555	0.1983	0.9941	0.099*	0.378 (11)
H15D	0.4733	0.2479	1.1215	0.099*	0.378 (11)
C16	0.5353 (10)	0.3408 (6)	1.0727 (9)	0.174 (4)	0.622 (11)
H16A	0.4767	0.3931	1.0603	0.209*	0.622 (11)
H16B	0.6166	0.3535	1.1483	0.209*	0.622 (11)
C16'	0.4644 (9)	0.3432 (6)	0.9833 (10)	0.100 (3)	0.378 (11)
H16C	0.4288	0.3431	0.8907	0.120*	0.378 (11)
H16D	0.4274	0.3959	1.0083	0.120*	0.378 (11)
C17	0.5612 (12)	0.3325 (9)	0.9614 (9)	0.179 (4)	0.622 (11)
H17A	0.6154	0.2788	0.9714	0.269*	0.622 (11)
H17B	0.6053	0.3878	0.9543	0.269*	0.622 (11)
H17C	0.4800	0.3255	0.8854	0.269*	0.622 (11)
C17'	0.6098 (10)	0.3518 (14)	1.0427 (18)	0.194 (9)	0.378 (11)
H17D	0.6484	0.3093	1.1136	0.291*	0.378 (11)
H17E	0.6347	0.4148	1.0725	0.291*	0.378 (11)
H17F	0.6399	0.3370	0.9801	0.291*	0.378 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1169 (5)	0.0600 (4)	0.0808 (4)	−0.0027 (3)	0.0688 (4)	−0.0042 (3)
O1	0.1334 (13)	0.0518 (9)	0.0645 (8)	−0.0032 (8)	0.0578 (9)	−0.0075 (7)
N1	0.1108 (14)	0.0461 (10)	0.0552 (9)	0.0177 (9)	0.0447 (9)	0.0053 (7)
N2	0.1050 (12)	0.0456 (9)	0.0533 (9)	0.0107 (8)	0.0445 (9)	0.0074 (7)
N3	0.142 (5)	0.057 (2)	0.080 (3)	0.027 (3)	0.075 (4)	0.017 (2)
N3'	0.087 (6)	0.043 (3)	0.047 (4)	0.017 (4)	0.035 (4)	0.007 (3)
C1	0.0655 (11)	0.0501 (11)	0.0567 (10)	0.0086 (9)	0.0237 (9)	0.0051 (8)
C2	0.1061 (17)	0.0522 (13)	0.0719 (13)	0.0070 (11)	0.0378 (12)	0.0010 (10)
C3	0.1158 (19)	0.0537 (14)	0.0965 (18)	−0.0102 (13)	0.0384 (16)	−0.0010 (13)
C4	0.112 (2)	0.0737 (18)	0.109 (2)	−0.0186 (15)	0.0540 (17)	0.0101 (15)
C5	0.1149 (19)	0.0739 (17)	0.1055 (19)	−0.0128 (14)	0.0718 (16)	0.0048 (14)
C6	0.0756 (13)	0.0568 (12)	0.0731 (12)	0.0011 (9)	0.0393 (11)	0.0019 (10)
C7	0.0678 (11)	0.0480 (11)	0.0457 (9)	0.0132 (8)	0.0222 (8)	0.0056 (8)
C8	0.0749 (12)	0.0507 (11)	0.0504 (10)	0.0084 (9)	0.0329 (9)	0.0028 (8)
C9	0.0841 (13)	0.0485 (11)	0.0482 (10)	0.0082 (9)	0.0343 (9)	0.0024 (8)
C10	0.1190 (17)	0.0495 (12)	0.0595 (11)	0.0226 (11)	0.0538 (12)	0.0090 (9)
C11	0.212 (8)	0.070 (3)	0.125 (5)	0.050 (5)	0.132 (6)	0.024 (3)
C11'	0.175 (13)	0.053 (6)	0.055 (6)	0.052 (8)	0.078 (8)	0.018 (4)
C12	0.126 (4)	0.135 (5)	0.105 (3)	0.038 (3)	0.063 (3)	−0.008 (3)
C12'	0.204 (15)	0.134 (14)	0.103 (8)	0.106 (12)	0.065 (8)	0.010 (7)
C13	0.131 (6)	0.111 (6)	0.210 (11)	−0.033 (4)	0.109 (7)	−0.089 (7)
C13'	0.221 (19)	0.089 (10)	0.040 (5)	0.019 (10)	0.028 (6)	−0.016 (5)
C14	0.126 (7)	0.059 (3)	0.053 (4)	0.006 (4)	0.041 (5)	0.013 (2)
C14'	0.088 (6)	0.038 (3)	0.049 (6)	0.004 (4)	0.039 (5)	0.002 (3)
C15	0.113 (5)	0.155 (6)	0.090 (5)	−0.047 (4)	0.022 (4)	0.025 (4)
C15'	0.078 (6)	0.084 (5)	0.080 (6)	−0.012 (4)	0.032 (5)	0.014 (4)
C16	0.145 (7)	0.237 (10)	0.135 (8)	−0.084 (6)	0.058 (6)	−0.015 (6)
C16'	0.112 (6)	0.109 (6)	0.073 (5)	−0.034 (5)	0.034 (5)	−0.001 (4)
C17	0.162 (9)	0.259 (12)	0.140 (7)	−0.051 (8)	0.088 (7)	0.006 (8)
C17'	0.157 (12)	0.262 (19)	0.145 (14)	−0.116 (13)	0.052 (10)	0.013 (14)

Geometric parameters (Å, º) top

N3—C11	1.482 (9)	C12'—H12D	0.9600
N3—H3A	0.8600	C12'—H12E	0.9600
N3'—C11'	1.387 (16)	C12'—H12F	0.9600
N3'—H3'	0.8600	C13—H13A	0.9600
C1—C2	1.392 (3)	C13—H13B	0.9600
C1—C6	1.397 (3)	C13—H13C	0.9600
C1—C7	1.448 (3)	C13'—H13D	0.9600
C2—C3	1.374 (3)	C13'—H13E	0.9600
C2—H2	0.9300	C13'—H13F	0.9600
C3—C4	1.384 (4)	C14—C15	1.507 (7)
C3—H3	0.9300	C14—N2	1.544 (7)
C4—C5	1.364 (4)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.395 (3)	C14'—N2	1.452 (9)
C5—H5	0.9300	C14'—C15'	1.528 (9)
C6—S1	1.743 (2)	C14'—H14C	0.9700
C7—N1	1.359 (3)	C14'—H14D	0.9700
C7—C8	1.369 (3)	C15—C16	1.528 (7)
C8—C9	1.416 (3)	C15—H15A	0.9700
C8—S1	1.741 (2)	C15—H15B	0.9700
C9—O1	1.235 (2)	C15'—C16'	1.531 (8)
C9—N2	1.405 (2)	C15'—H15C	0.9700
C10—N1	1.308 (3)	C15'—H15D	0.9700
C10—N3'	1.361 (10)	C16—C17	1.461 (8)
C10—N2	1.389 (3)	C16—H16A	0.9700
C10—N3	1.394 (5)	C16—H16B	0.9700
C11—C13	1.490 (7)	C16'—C17'	1.493 (9)
C11—C12	1.508 (7)	C16'—H16C	0.9700
C11—H11	0.9800	C16'—H16D	0.9700
C11'—C13'	1.499 (9)	C17—H17A	0.9600
C11'—C12'	1.510 (9)	C17—H17B	0.9600
C11'—H11'	0.9800	C17—H17C	0.9600
C12—H12A	0.9600	C17'—H17D	0.9600
C12—H12B	0.9600	C17'—H17E	0.9600
C12—H12C	0.9600	C17'—H17F	0.9600

C8—S1—C6	90.27 (10)	C12'—C11'—H11'	102.4
C10—N1—C7	115.57 (16)	C11'—C12'—H12D	109.5
C10—N2—C9	121.65 (17)	C11'—C12'—H12E	109.5
C10—N2—C14'	119.9 (6)	H12D—C12'—H12E	109.5
C9—N2—C14'	118.0 (6)	C11'—C12'—H12F	109.5
C10—N2—C14	121.9 (4)	H12D—C12'—H12F	109.5
C9—N2—C14	115.1 (4)	H12E—C12'—H12F	109.5
C10—N3—C11	122.4 (6)	C11'—C13'—H13D	109.5
C10—N3—H3A	118.8	C11'—C13'—H13E	109.5
C11—N3—H3A	118.8	H13D—C13'—H13E	109.5
C10—N3'—C11'	121.0 (10)	C11'—C13'—H13F	109.5
C10—N3'—H3'	119.5	H13D—C13'—H13F	109.5
C11'—N3'—H3'	119.5	H13E—C13'—H13F	109.5
C2—C1—C6	119.5 (2)	C15—C14—N2	116.4 (6)
C2—C1—C7	129.1 (2)	C15—C14—H14A	108.2
C6—C1—C7	111.39 (18)	N2—C14—H14A	108.2
C3—C2—C1	119.2 (2)	C15—C14—H14B	108.2
C3—C2—H2	120.4	N2—C14—H14B	108.2
C1—C2—H2	120.4	H14A—C14—H14B	107.3
C2—C3—C4	121.1 (2)	N2—C14'—C15'	103.6 (7)
C2—C3—H3	119.5	N2—C14'—H14C	111.0
C4—C3—H3	119.5	C15'—C14'—H14C	111.0
C5—C4—C3	120.5 (2)	N2—C14'—H14D	111.0
C5—C4—H4	119.7	C15'—C14'—H14D	111.0
C3—C4—H4	119.7	H14C—C14'—H14D	109.0
C4—C5—C6	119.4 (3)	C14—C15—C16	111.7 (6)
C4—C5—H5	120.3	C14—C15—H15A	109.3
C6—C5—H5	120.3	C16—C15—H15A	109.3
C5—C6—C1	120.2 (2)	C14—C15—H15B	109.3
C5—C6—S1	127.07 (19)	C16—C15—H15B	109.3
C1—C6—S1	112.71 (16)	H15A—C15—H15B	107.9
N1—C7—C8	124.20 (18)	C14'—C15'—C16'	107.1 (7)
N1—C7—C1	123.82 (17)	C14'—C15'—H15C	110.3
C8—C7—C1	111.94 (18)	C16'—C15'—H15C	110.3
C7—C8—C9	121.09 (18)	C14'—C15'—H15D	110.3
C7—C8—S1	113.69 (15)	C16'—C15'—H15D	110.3
C9—C8—S1	125.23 (15)	H15C—C15'—H15D	108.5
O1—C9—N2	120.20 (18)	C17—C16—C15	111.5 (7)
O1—C9—C8	126.63 (18)	C17—C16—H16A	109.3
N2—C9—C8	113.17 (16)	C15—C16—H16A	109.3
N1—C10—N3'	113.4 (6)	C17—C16—H16B	109.3
N1—C10—N2	124.28 (18)	C15—C16—H16B	109.3
N3'—C10—N2	119.7 (5)	H16A—C16—H16B	108.0
N1—C10—N3	120.3 (3)	C17'—C16'—C15'	108.7 (7)
N2—C10—N3	114.6 (3)	C17'—C16'—H16C	109.9
N3—C11—C13	107.2 (6)	C15'—C16'—H16C	109.9
N3—C11—C12	106.0 (6)	C17'—C16'—H16D	109.9
C13—C11—C12	111.5 (5)	C15'—C16'—H16D	109.9
N3—C11—H11	110.7	H16C—C16'—H16D	108.3
C13—C11—H11	110.7	C16'—C17'—H17D	109.5
C12—C11—H11	110.7	C16'—C17'—H17E	109.5
N3'—C11'—C13'	113.8 (11)	H17D—C17'—H17E	109.5
N3'—C11'—C12'	122.5 (11)	C16'—C17'—H17F	109.5
C13'—C11'—C12'	110.1 (8)	H17D—C17'—H17F	109.5
N3'—C11'—H11'	102.4	H17E—C17'—H17F	109.5
C13'—C11'—H11'	102.4

C6—C1—C2—C3	0.3 (3)	C14—C15—C16—C17	−84.7 (12)
C7—C1—C2—C3	−178.9 (2)	N2—C14'—C15'—C16'	178.1 (8)
C1—C2—C3—C4	−0.2 (4)	C14'—C15'—C16'—C17'	172.6 (15)
C2—C3—C4—C5	−0.1 (4)	N3'—C10—N1—C7	−160.1 (5)
C3—C4—C5—C6	0.3 (4)	N2—C10—N1—C7	1.3 (3)
C4—C5—C6—C1	−0.1 (4)	N3—C10—N1—C7	170.8 (4)
C4—C5—C6—S1	179.2 (2)	C8—C7—N1—C10	0.5 (3)
C2—C1—C6—C5	−0.2 (3)	C1—C7—N1—C10	178.05 (18)
C7—C1—C6—C5	179.2 (2)	N1—C10—N2—C9	−2.2 (3)
C2—C1—C6—S1	−179.60 (17)	N3'—C10—N2—C9	158.1 (6)
C7—C1—C6—S1	−0.2 (2)	N3—C10—N2—C9	−172.3 (4)
C2—C1—C7—N1	1.2 (3)	N1—C10—N2—C14'	−173.8 (6)
C6—C1—C7—N1	−178.14 (17)	N3'—C10—N2—C14'	−13.5 (8)
C2—C1—C7—C8	178.9 (2)	N3—C10—N2—C14'	16.1 (7)
C6—C1—C7—C8	−0.4 (2)	N1—C10—N2—C14	164.2 (4)
N1—C7—C8—C9	−1.5 (3)	N3'—C10—N2—C14	−35.5 (7)
C1—C7—C8—C9	−179.22 (17)	N3—C10—N2—C14	−5.9 (6)
N1—C7—C8—S1	178.56 (15)	O1—C9—N2—C10	−179.5 (2)
C1—C7—C8—S1	0.8 (2)	C8—C9—N2—C10	1.1 (3)
C7—C8—C9—O1	−178.78 (19)	O1—C9—N2—C14'	−7.7 (6)
S1—C8—C9—O1	1.2 (3)	C8—C9—N2—C14'	172.9 (5)
C7—C8—C9—N2	0.5 (3)	O1—C9—N2—C14	13.3 (4)
S1—C8—C9—N2	−179.48 (14)	C8—C9—N2—C14	−166.1 (4)
N1—C10—N3—C11	0.8 (8)	C15'—C14'—N2—C10	−80.9 (8)
N3'—C10—N3—C11	−81.1 (18)	C15'—C14'—N2—C9	107.1 (8)
N2—C10—N3—C11	171.4 (5)	C15'—C14'—N2—C14	21 (2)
C10—N3—C11—C13	95.4 (8)	C15—C14—N2—C10	−82.4 (8)
C10—N3—C11—C12	−145.4 (7)	C15—C14—N2—C9	84.8 (8)
N1—C10—N3'—C11'	−25.1 (12)	C15—C14—N2—C14'	−172 (3)
N2—C10—N3'—C11'	172.6 (9)	C7—C8—S1—C6	−0.77 (16)
N3—C10—N3'—C11'	86.3 (17)	C9—C8—S1—C6	179.24 (19)
C10—N3'—C11'—C13'	161.8 (14)	C5—C6—S1—C8	−178.8 (2)
C10—N3'—C11'—C12'	−61.6 (18)	C1—C6—S1—C8	0.55 (16)
N2—C14—C15—C16	178.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.97	2.52	3.478 (9)	171
N3—H3A···O1ⁱ	0.86	2.46	3.140 (6)	137

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃OS
M_r	315.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.4322 (6), 14.2791 (8), 11.6704 (6)
β (°)	116.606 (1)
V (Å³)	1703.36 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15640, 3712, 2599
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.175, 1.04
No. of reflections	3712
No. of parameters	279
No. of restraints	23
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.16

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.97	2.52	3.478 (9)	171.1
N3—H3A···O1ⁱ	0.86	2.46	3.140 (6)	136.9

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The author acknowledges the National Basic Research Program of China (grant No. 2004CCA00100) and the National Natural Science Foundation of China (grant No. 20102001).

References

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