9-Ethyl-3,6-bis-(5-iodo-2-thien-yl)-9H-carbazole.

In the title compound, C(22)H(15)I(2)NS(2), the two thio-phene 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 mol-ecules are linked into centrosymmetric dimers by pairs of C-H⋯I inter-actions.

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 = 611.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.151

S = 1.16

3738 reflections

245 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.79 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.

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536810004484/rk2188sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H15I2NS2	F(000) = 1168
Mr = 611.29	Dx = 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

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

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(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3738 reflections	(Δ/σ)max = 0.002
245 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.79 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .