9-Ethyl-3,6-bis­(5-iodo-2-thien­yl)-9H-carbazole

Xu, G.-Y.; Geng, W.-Q.; Zhou, H.-P.

doi:10.1107/S1600536810004484

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o571

doi:10.1107/S1600536810004484

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9-Ethyl-3,6-bis(5-iodo-2-thienyl)-9H-carbazole

Guo-Yi Xu,^a Wen-Qian Geng ^a and Hong-Ping Zhou ^a ^*

^aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China and, Key Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 2 February 2010; accepted 4 February 2010; online 10 February 2010)

In the title compound, C₂₂H₁₅I₂NS₂, the two thiophene rings are twisted out of the plane of the central pyrrole ring, making dihedral angles of 32.4 (2)° and 9.8 (2). In the crystal, neighboring molecules are linked into centrosymmetric dimers by pairs of C—H⋯I interactions.

Related literature

For the crystal structures of related carbazole derivatives, see: Yang et al. (2005 ); Zhou et al. (2007 ); Zhou et al. (2008 ); Chen et al. (2009 ).

Experimental

Crystal data

C₂₂H₁₅I₂NS₂
M_r = 611.29
Monoclinic, P 2₁ /c
a = 10.637 (3) Å
b = 7.814 (2) Å
c = 26.687 (7) Å
β = 107.313 (18)°
V = 2117.7 (10) Å³
Z = 4
Mo Kα radiation
μ = 3.17 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.449, T_max = 0.742
17471 measured reflections
3738 independent reflections
3065 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.151
S = 1.16
3738 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯I1ⁱ	0.93	3.15	4.040 (9)	161
Symmetry code: (i) -x, -y+3, -z+2.

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/S1600536810004484/rk2188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004484/rk2188Isup2.hkl

checkCIF report

Comment top

Carbazole - based materials had been investigated for their electrical and optical properties. Especially, introduction of substituents on the 3- and 6-positions of carbazole represents a possible approach for designing carbazole-based photorefractive materials (Yang et al., 2005). The title molecule that we has designed and synthesized is a good intermediate and penetratingly investigated. In the title molecule (Fig.1), the bond lengths and angles show normal values (Chen et al., 2009; Zhou et al., 2007, 2008). Two thiophene rings are twisted out of the plane of the center pyrrole ring and the dihedral angles are 32.4 (2)° and 9.8 (2)°, respectively. In the crystal structure of title compound (Fig.2), the neighboring molecules form a centrosymmetric dimer by C17—H17···I1ⁱ (symmetry code: (i) -x, 3-y, 2-z). The neighboring dimers are stacked through weak π···π interaction and the face-to-face distance between two neighboring thiophene rings is 3.57 (4)Å.

Related literature top

For the crystal structures of related carbazole derivatives, see: Yang et al. (2005); Zhou et al. (2007); Zhou et al. (2008); Chen et al. (2009).

Experimental top

Preparation of 9-ethyl-3,6-diiodocarbazole: 9-ethylcarbazole (10 g, 51 mmol) and anhydrous ethanol (150 ml) were added to a three-necked flask equipped with a magnetic stirrer, a reflux condenser and an isobaric dropping funnel. ICl (20 g, 123 mmol)/ethanol (20 ml) was added to the mixture at 353 K. The reaction mixture was refluxed for 2 h, cooled to room temperature and filtered. The grey needle crystals (20.52 g, yield 90%) were obtained and washed with ethanol.

Preparation of 9-ethyl-3,6-di(2-thienyl)carbazole: a 80 ml three-necked round-bottomed flask was charged with of 9-ethyl-3,6-diiodocarbazole (3.00 g, 6 mmol), 10 ml of DMF, 10 ml of Et₃N and thiophen-2-yl-boronic acid (2.55 g, 20 mmol). A catalytic amount of Pd(OAc)₂ was added to the stirring solution at 343 K after 9-ethyl-3,6-diiodocarbazole was completely dissolved under nitrogen. The solution was refluxed for 6 h at 403 K. At the end of the reaction was judged by TLC analysis. The solution was cooled to room temperature and dissolved in 200 ml CH₂Cl₂, then washed with water (3× 200 ml), dried over anhydrous MgSO₄, brown column crystals were obtained (2.00 g, yield 80% ).

Preparation of 9-ethyl-3,6-di{2-[(5-iodo)thiophene]-yl}carbazole: a 50 ml round-bottomed flask was charged with 9-ethyl-3,6-di(2-thienyl)carbazole (0.13 g, 0.3 mmol) and 9 ml of acetone. A N-iodosuccinimide (0.42 g, 1.9 mmol) dissolved in 4 ml acetone and was added to the stirring solution at room temperature after 9-ethyl-3,6-di(2-thienyl)carbazole was completely dissolved. At the end of the reaction was judged by TLC analysis after 4 h. The solution was dissolved in 100 ml CH₂Cl₂, then washed with water (3× 200 ml), dried over anhydrous MgSO₄. The organic layer was concentrated in vacuum, the orange suspended solution was decanted out of the flask after 3 ml ethanol was added, green crystals were obtained (0.14 g, yield 54%).

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 withb the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing diagram of the title compound. Dashed lines indicate a centrosymmetric dimer C17—H17···I1ⁱ. Symmetry code: (i) -x, 3-y, 2-z). H atoms not involved in hydrogen bonds are omitted for clarity.

9-Ethyl-3,6-bis(5-iodo-2-thienyl)-9H-carbazole top

Crystal data top

C₂₂H₁₅I₂NS₂	F(000) = 1168
M_r = 611.29	D_x = 1.917 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 7193 reflections
a = 10.637 (3) Å	θ = 2.4–27.4°
b = 7.814 (2) Å	µ = 3.17 mm⁻¹
c = 26.687 (7) Å	T = 298 K
β = 107.313 (18)°	Prism, green
V = 2117.7 (10) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3738 independent reflections
Radiation source: fine-focus sealed tube	3065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ– and ω–scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.449, T_max = 0.742	k = −9→9
17471 measured reflections	l = −31→30

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3738 reflections	(Δ/σ)_max = 0.002
245 parameters	Δρ_max = 1.08 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

C₂₂H₁₅I₂NS₂	V = 2117.7 (10) Å³
M_r = 611.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.637 (3) Å	µ = 3.17 mm⁻¹
b = 7.814 (2) Å	T = 298 K
c = 26.687 (7) Å	0.30 × 0.20 × 0.10 mm
β = 107.313 (18)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3738 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3065 reflections with I > 2σ(I)
T_min = 0.449, T_max = 0.742	R_int = 0.022
17471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.16	Δρ_max = 1.08 e Å⁻³
3738 reflections	Δρ_min = −0.79 e Å⁻³
245 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
I1	0.25459 (4)	1.46648 (5)	1.073693 (15)	0.0711 (2)
I2	−0.70485 (4)	0.47106 (5)	0.685869 (19)	0.0818 (2)
S1	0.28672 (13)	1.0941 (2)	1.02087 (5)	0.0797 (5)
S2	−0.39715 (12)	0.45973 (15)	0.75996 (5)	0.0589 (3)
N1	0.2462 (4)	0.3710 (7)	0.87990 (17)	0.0768 (13)
C1	0.3499 (4)	0.6105 (8)	0.94135 (18)	0.0651 (13)
H1	0.4337	0.5626	0.9523	0.078*
C2	0.3241 (4)	0.7652 (8)	0.96071 (18)	0.0631 (12)
H2	0.3925	0.8228	0.9847	0.076*
C3	0.1979 (4)	0.8397 (7)	0.94558 (16)	0.0550 (11)
C4	0.0960 (4)	0.7564 (6)	0.90838 (16)	0.0532 (10)
H4	0.0125	0.8050	0.8974	0.064*
C5	−0.0883 (5)	0.4929 (6)	0.81521 (18)	0.0513 (11)
H5	−0.1440	0.5816	0.8182	0.062*
C6	−0.1344 (4)	0.3655 (6)	0.77807 (17)	0.0543 (11)
C7	−0.0498 (5)	0.2311 (7)	0.7748 (2)	0.0721 (14)
H7	−0.0812	0.1450	0.7502	0.087*
C8	0.0776 (5)	0.2224 (8)	0.8067 (2)	0.0792 (16)
H8	0.1326	0.1332	0.8035	0.095*
C9	0.1219 (5)	0.3487 (7)	0.8434 (2)	0.0674 (13)
C10	0.0396 (5)	0.4886 (6)	0.84774 (19)	0.0526 (11)
C11	0.1197 (4)	0.6004 (6)	0.88770 (16)	0.0504 (10)
C12	0.2465 (5)	0.5279 (7)	0.9049 (2)	0.0612 (13)
C13	0.3602 (6)	0.2581 (11)	0.8866 (3)	0.101 (2)
H13A	0.4207	0.2705	0.9217	0.121*
H13B	0.3318	0.1397	0.8817	0.121*
C14	0.4210 (8)	0.3038 (11)	0.8499 (3)	0.120 (3)
H14A	0.4396	0.4243	0.8525	0.180*
H14B	0.3641	0.2781	0.8154	0.180*
H14C	0.5018	0.2411	0.8560	0.180*
C15	0.1743 (5)	1.0054 (6)	0.96736 (18)	0.0521 (11)
C16	0.0690 (6)	1.1130 (8)	0.9511 (3)	0.0900 (19)
H16	−0.0044	1.0889	0.9227	0.108*
C17	0.0809 (6)	1.2599 (9)	0.9803 (3)	0.098 (2)
H17	0.0165	1.3445	0.9732	0.117*
C18	0.1926 (4)	1.2712 (6)	1.01974 (17)	0.0570 (11)
C19	−0.2682 (4)	0.3707 (6)	0.74207 (17)	0.0520 (10)
C20	−0.3136 (5)	0.3054 (7)	0.69241 (19)	0.0640 (13)
H20	−0.2592	0.2528	0.6754	0.077*
C21	−0.4518 (5)	0.3255 (7)	0.6691 (2)	0.0672 (13)
H21	−0.4972	0.2872	0.6356	0.081*
C22	−0.5089 (4)	0.4058 (6)	0.7009 (2)	0.0599 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0604 (3)	0.0777 (3)	0.0697 (3)	0.00741 (16)	0.0107 (2)	−0.00697 (16)
I2	0.0464 (3)	0.0720 (3)	0.1149 (4)	0.00143 (15)	0.0054 (2)	−0.02046 (19)
S1	0.0533 (8)	0.1005 (10)	0.0672 (8)	0.0256 (8)	−0.0095 (6)	−0.0250 (8)
S2	0.0444 (7)	0.0653 (8)	0.0655 (8)	0.0031 (5)	0.0137 (6)	−0.0110 (5)
N1	0.047 (2)	0.089 (3)	0.086 (3)	0.019 (2)	0.007 (2)	−0.025 (2)
C1	0.041 (2)	0.091 (4)	0.059 (3)	0.017 (3)	0.007 (2)	−0.006 (3)
C2	0.038 (2)	0.093 (4)	0.050 (2)	0.009 (2)	0.0012 (18)	−0.001 (2)
C3	0.041 (2)	0.080 (3)	0.043 (2)	0.007 (2)	0.0110 (18)	0.003 (2)
C4	0.041 (2)	0.071 (3)	0.047 (2)	0.004 (2)	0.0113 (18)	0.005 (2)
C5	0.040 (2)	0.058 (2)	0.059 (3)	0.0080 (19)	0.020 (2)	0.005 (2)
C6	0.044 (2)	0.064 (3)	0.058 (3)	−0.003 (2)	0.0201 (19)	−0.004 (2)
C7	0.053 (3)	0.073 (3)	0.089 (4)	0.001 (3)	0.020 (3)	−0.025 (3)
C8	0.055 (3)	0.081 (4)	0.097 (4)	0.018 (3)	0.016 (3)	−0.027 (3)
C9	0.042 (2)	0.080 (3)	0.077 (3)	0.015 (3)	0.012 (2)	−0.008 (3)
C10	0.042 (3)	0.060 (2)	0.057 (3)	0.005 (2)	0.018 (2)	−0.001 (2)
C11	0.040 (2)	0.068 (3)	0.045 (2)	0.010 (2)	0.0170 (18)	0.004 (2)
C12	0.040 (3)	0.081 (3)	0.062 (3)	0.011 (2)	0.013 (2)	−0.004 (2)
C13	0.070 (4)	0.129 (6)	0.107 (5)	0.007 (4)	0.032 (4)	−0.041 (5)
C14	0.100 (5)	0.111 (6)	0.141 (7)	−0.020 (5)	0.023 (5)	−0.026 (5)
C15	0.038 (2)	0.068 (3)	0.045 (2)	0.004 (2)	0.0054 (19)	0.0058 (19)
C16	0.060 (3)	0.079 (4)	0.101 (4)	0.018 (3)	−0.023 (3)	−0.016 (3)
C17	0.070 (4)	0.077 (4)	0.116 (5)	0.023 (3)	−0.019 (3)	−0.015 (4)
C18	0.044 (2)	0.065 (3)	0.056 (3)	0.004 (2)	0.0054 (19)	0.004 (2)
C19	0.043 (2)	0.051 (2)	0.063 (3)	−0.003 (2)	0.0174 (19)	−0.005 (2)
C20	0.055 (3)	0.076 (3)	0.064 (3)	−0.004 (3)	0.022 (2)	−0.017 (2)
C21	0.053 (3)	0.069 (3)	0.074 (3)	−0.008 (3)	0.011 (2)	−0.025 (3)
C22	0.044 (2)	0.050 (2)	0.080 (3)	−0.005 (2)	0.010 (2)	−0.008 (2)

Geometric parameters (Å, º) top

I1—C18	2.066 (5)	C7—C8	1.371 (7)
I2—C22	2.066 (5)	C7—H7	0.9300
S1—C18	1.703 (5)	C8—C9	1.372 (7)
S1—C15	1.713 (5)	C8—H8	0.9300
S2—C22	1.720 (5)	C9—C10	1.427 (7)
S2—C19	1.727 (4)	C10—C11	1.444 (7)
N1—C12	1.395 (7)	C11—C12	1.408 (6)
N1—C9	1.400 (6)	C13—C14	1.373 (9)
N1—C13	1.466 (8)	C13—H13A	0.9700
C1—C2	1.374 (8)	C13—H13B	0.9700
C1—C12	1.392 (7)	C14—H14A	0.9600
C1—H1	0.9300	C14—H14B	0.9600
C2—C3	1.407 (6)	C14—H14C	0.9600
C2—H2	0.9300	C15—C16	1.364 (7)
C3—C4	1.394 (6)	C16—C17	1.373 (9)
C3—C15	1.471 (7)	C16—H16	0.9300
C4—C11	1.392 (7)	C17—C18	1.336 (7)
C4—H4	0.9300	C17—H17	0.9300
C5—C10	1.380 (7)	C19—C20	1.367 (6)
C5—C6	1.387 (6)	C20—C21	1.425 (7)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.403 (7)	C21—C22	1.338 (7)
C6—C19	1.462 (6)	C21—H21	0.9300

C18—S1—C15	93.1 (2)	C1—C12—C11	121.5 (5)
C22—S2—C19	92.1 (2)	N1—C12—C11	109.5 (4)
C12—N1—C9	108.0 (4)	C14—C13—N1	107.7 (7)
C12—N1—C13	125.9 (5)	C14—C13—H13A	110.2
C9—N1—C13	125.8 (5)	N1—C13—H13A	110.2
C2—C1—C12	117.8 (4)	C14—C13—H13B	110.2
C2—C1—H1	121.1	N1—C13—H13B	110.2
C12—C1—H1	121.1	H13A—C13—H13B	108.5
C1—C2—C3	122.5 (5)	C13—C14—H14A	109.5
C1—C2—H2	118.8	C13—C14—H14B	109.5
C3—C2—H2	118.8	H14A—C14—H14B	109.5
C4—C3—C2	119.0 (5)	C13—C14—H14C	109.5
C4—C3—C15	120.3 (4)	H14A—C14—H14C	109.5
C2—C3—C15	120.8 (4)	H14B—C14—H14C	109.5
C11—C4—C3	119.8 (4)	C16—C15—C3	129.6 (5)
C11—C4—H4	120.1	C16—C15—S1	108.6 (4)
C3—C4—H4	120.1	C3—C15—S1	121.8 (3)
C10—C5—C6	120.3 (4)	C15—C16—C17	114.0 (5)
C10—C5—H5	119.9	C15—C16—H16	123.0
C6—C5—H5	119.9	C17—C16—H16	123.0
C5—C6—C7	119.0 (4)	C18—C17—C16	114.4 (5)
C5—C6—C19	121.2 (4)	C18—C17—H17	122.8
C7—C6—C19	119.8 (4)	C16—C17—H17	122.8
C8—C7—C6	122.2 (5)	C17—C18—S1	109.9 (4)
C8—C7—H7	118.9	C17—C18—I1	128.5 (4)
C6—C7—H7	118.9	S1—C18—I1	121.6 (2)
C7—C8—C9	118.2 (5)	C20—C19—C6	128.3 (4)
C7—C8—H8	120.9	C20—C19—S2	109.8 (3)
C9—C8—H8	120.9	C6—C19—S2	121.9 (3)
C8—C9—N1	129.7 (5)	C19—C20—C21	113.7 (4)
C8—C9—C10	121.4 (5)	C19—C20—H20	123.1
N1—C9—C10	108.9 (4)	C21—C20—H20	123.1
C5—C10—C9	118.8 (4)	C22—C21—C20	112.2 (4)
C5—C10—C11	134.8 (4)	C22—C21—H21	123.9
C9—C10—C11	106.4 (4)	C20—C21—H21	123.9
C4—C11—C12	119.5 (4)	C21—C22—S2	112.1 (4)
C4—C11—C10	133.3 (4)	C21—C22—I2	127.9 (4)
C12—C11—C10	107.1 (4)	S2—C22—I2	120.0 (3)
C1—C12—N1	129.1 (4)

C12—C1—C2—C3	1.0 (8)	C13—N1—C12—C11	178.7 (6)
C1—C2—C3—C4	−2.0 (8)	C4—C11—C12—C1	−1.4 (7)
C1—C2—C3—C15	179.8 (5)	C10—C11—C12—C1	176.1 (5)
C2—C3—C4—C11	1.3 (7)	C4—C11—C12—N1	178.6 (4)
C15—C3—C4—C11	179.5 (4)	C10—C11—C12—N1	−3.9 (6)
C10—C5—C6—C7	1.2 (7)	C12—N1—C13—C14	−90.0 (8)
C10—C5—C6—C19	−178.0 (4)	C9—N1—C13—C14	83.0 (9)
C5—C6—C7—C8	−0.9 (8)	C4—C3—C15—C16	−12.0 (8)
C19—C6—C7—C8	178.3 (5)	C2—C3—C15—C16	166.2 (6)
C6—C7—C8—C9	1.2 (9)	C4—C3—C15—S1	168.4 (4)
C7—C8—C9—N1	−179.2 (6)	C2—C3—C15—S1	−13.4 (6)
C7—C8—C9—C10	−1.7 (9)	C18—S1—C15—C16	−0.7 (5)
C12—N1—C9—C8	174.0 (6)	C18—S1—C15—C3	179.0 (4)
C13—N1—C9—C8	0.0 (11)	C3—C15—C16—C17	−178.9 (6)
C12—N1—C9—C10	−3.7 (6)	S1—C15—C16—C17	0.8 (8)
C13—N1—C9—C10	−177.7 (6)	C15—C16—C17—C18	−0.5 (10)
C6—C5—C10—C9	−1.8 (7)	C16—C17—C18—S1	0.0 (8)
C6—C5—C10—C11	176.5 (5)	C16—C17—C18—I1	179.7 (5)
C8—C9—C10—C5	2.1 (8)	C15—S1—C18—C17	0.4 (5)
N1—C9—C10—C5	180.0 (5)	C15—S1—C18—I1	−179.4 (3)
C8—C9—C10—C11	−176.6 (5)	C5—C6—C19—C20	151.0 (5)
N1—C9—C10—C11	1.3 (6)	C7—C6—C19—C20	−28.1 (8)
C3—C4—C11—C12	0.4 (7)	C5—C6—C19—S2	−31.6 (6)
C3—C4—C11—C10	−176.4 (5)	C7—C6—C19—S2	149.2 (4)
C5—C10—C11—C4	0.2 (9)	C22—S2—C19—C20	0.6 (4)
C9—C10—C11—C4	178.5 (5)	C22—S2—C19—C6	−177.3 (4)
C5—C10—C11—C12	−176.8 (5)	C6—C19—C20—C21	177.0 (5)
C9—C10—C11—C12	1.5 (5)	S2—C19—C20—C21	−0.6 (6)
C2—C1—C12—N1	−179.3 (5)	C19—C20—C21—C22	0.4 (7)
C2—C1—C12—C11	0.7 (8)	C20—C21—C22—S2	0.1 (6)
C9—N1—C12—C1	−175.2 (6)	C20—C21—C22—I2	178.7 (4)
C13—N1—C12—C1	−1.2 (10)	C19—S2—C22—C21	−0.4 (4)
C9—N1—C12—C11	4.7 (7)	C19—S2—C22—I2	−179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···I1ⁱ	0.93	3.15	4.040 (9)	161

Symmetry code: (i) −x, −y+3, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅I₂NS₂
M_r	611.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.637 (3), 7.814 (2), 26.687 (7)
β (°)	107.313 (18)
V (Å³)	2117.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.17
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.449, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	17471, 3738, 3065
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.151, 1.16
No. of reflections	3738
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.79

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···I1ⁱ	0.93	3.149	4.040 (9)	161.1

Symmetry code: (i) −x, −y+3, −z+2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 50703001, 20771001), the Education Committee of Anhui Province (grant No. KJ2009A52), the Young Teacher Foundation of Institutions of Higher Education of An Hui Province (grant No. 2007jq1019), the Ministry of Education and the Person with Ability Foundation of Anhui University.

References

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