9-(2-Thien­yl)-9H-carbazole

Jiang, X.-L.; Li, F.-R.; Zheng, R.-H.

doi:10.1107/S1600536808037173

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2461

doi:10.1107/S1600536808037173

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9-(2-Thienyl)-9H-carbazole

Xu-Liang Jiang,^a ^* Feng-Rong Li ^a and Ren-Hua Zheng ^b

^aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China, and ^bSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai, 317000, People's Republic of China
^*Correspondence e-mail: jiangxuliang@zj.com

(Received 5 October 2008; accepted 10 November 2008; online 26 November 2008)

In the title compound, C₁₆H₁₁NS, the dihedral angles between the fused ring system and the pendant thienyl ring are 86.37 (5) and 57.14 (5)°.

Related literature

For the fluorescence properties of 9-(2-thienyl)-9H-carbazole and its application in organic electroluminescent devices, including flat-panel displays, see: Wu et al. (2001 ).

Experimental

Crystal data

C₁₆H₁₁NS
M_r = 249.33
Monoclinic, P 2₁ /n
a = 14.412 (3) Å
b = 9.5831 (19) Å
c = 18.671 (4) Å
β = 100.64 (3)°
V = 2534.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.94, T_max = 0.97
26852 measured reflections
4980 independent reflections
4138 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections frequency: 60 min intensity decay: 0.3%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.080
S = 1.13
4980 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037173/sg2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037173/sg2270Isup2.hkl

checkCIF report

Comment top

Due to its excellent fluorescence properties, 9-(2-thienyl)-9H-carbazole can be used in organic electroluminescent devices, which have received considerable attention for their potential application in flat-panel displays (Wu et al., 2001). It was readily synthesized via Ullmann reaction with copper(I) iodide as catalyst from carbazole and 2-iodothiophene.

There are two crystallographically independent molecules in the sturcture of (I). The independent molecula is built up from a central core containing three fused rings and one pendant five-membered ring. (Fig. 1). In two independent molecules, the three fused rings are coplanar within 0.0493 (15) and 0.0135 (15) Å, respectively. The five-membered rings are coplanar within 0.0062 (13) and 0.0173 (12) Å, respectively. The dihedral angles between the two components are 86.37 (5) and 57.14 (5)°, respectively.

Related literature top

For the fluorescence properties of 9-(2-thienyl)-9H-carbazole and its application in organic electroluminescent devices, including flat-panel displays, see: Wu et al. (2001).

Experimental top

The title compound was synthesized via Ullmann reaction with copper(I) iodide as catalyst from carbazole and 2-iodothiophene. A solution of the compound in ethanol was concentrated gradually at room temperature to afford colorless prisms.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of (I), showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level.

9-(2-Thienyl)-9H-carbazole top

Crystal data top

C₁₆H₁₁NS	F(000) = 1040
M_r = 249.33	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7198 reflections
a = 14.412 (3) Å	θ = 2.1–23.5°
b = 9.5831 (19) Å	µ = 0.23 mm⁻¹
c = 18.671 (4) Å	T = 298 K
β = 100.64 (3)°	Prismatic, colorless
V = 2534.4 (9) Å³	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	4980 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω/2θ scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
T_min = 0.94, T_max = 0.97	k = −11→11
26852 measured reflections	l = −23→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0269P)² + 0.456P] where P = (F_o² + 2F_c²)/3
4980 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₆H₁₁NS	V = 2534.4 (9) Å³
M_r = 249.33	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.412 (3) Å	µ = 0.23 mm⁻¹
b = 9.5831 (19) Å	T = 298 K
c = 18.671 (4) Å	0.25 × 0.20 × 0.15 mm
β = 100.64 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4980 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4138 reflections with I > 2σ(I)
T_min = 0.94, T_max = 0.97	R_int = 0.035
26852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.13	Δρ_max = 0.11 e Å⁻³
4980 reflections	Δρ_min = −0.13 e Å⁻³
325 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
C1	0.63934 (12)	0.55497 (19)	0.16359 (10)	0.0479 (4)
C2	0.66476 (13)	0.5659 (2)	0.09552 (10)	0.0528 (4)
H2	0.6505	0.4940	0.0618	0.063*
C3	0.71148 (12)	0.68426 (19)	0.07780 (10)	0.0516 (4)
H3	0.7285	0.6916	0.0323	0.062*
C4	0.73279 (13)	0.7917 (2)	0.12815 (11)	0.0578 (5)
H4	0.7640	0.8709	0.1163	0.069*
C5	0.70737 (12)	0.78082 (19)	0.19622 (10)	0.0522 (4)
H5	0.7216	0.8527	0.2299	0.063*
C6	0.66065 (12)	0.66244 (19)	0.21394 (9)	0.0497 (4)
C7	0.62079 (12)	0.62015 (18)	0.27751 (9)	0.0472 (4)
C8	0.61740 (14)	0.6816 (2)	0.34441 (10)	0.0566 (5)
H8	0.6464	0.7674	0.3563	0.068*
C9	0.57060 (13)	0.6150 (2)	0.39353 (11)	0.0547 (5)
H9	0.5683	0.6562	0.4383	0.066*
C10	0.52720 (13)	0.4869 (2)	0.37576 (10)	0.0545 (5)
H10	0.4959	0.4423	0.4086	0.065*
C11	0.53059 (13)	0.4254 (2)	0.30887 (10)	0.0543 (5)
H11	0.5015	0.3397	0.2970	0.065*
C12	0.57739 (12)	0.49203 (18)	0.25974 (9)	0.0449 (4)
C13	0.55629 (13)	0.3243 (2)	0.15350 (10)	0.0550 (5)
C14	0.61217 (12)	0.19052 (17)	0.15100 (9)	0.0451 (4)
H14	0.6738	0.1687	0.1728	0.054*
C15	0.53843 (13)	0.1030 (2)	0.10260 (11)	0.0568 (5)
H15	0.5507	0.0114	0.0908	0.068*
C16	0.45484 (13)	0.1629 (2)	0.07748 (10)	0.0541 (5)
H16	0.4063	0.1168	0.0469	0.065*
C17	0.35787 (12)	0.10050 (16)	0.29912 (9)	0.0425 (4)
C18	0.43576 (12)	0.06295 (18)	0.26924 (10)	0.0497 (4)
H18	0.4295	0.0512	0.2191	0.060*
C19	0.52295 (13)	0.0429 (2)	0.31425 (9)	0.0519 (4)
H19	0.5751	0.0178	0.2943	0.062*
C20	0.53225 (13)	0.0605 (2)	0.38914 (10)	0.0549 (5)
H20	0.5906	0.0471	0.4193	0.066*
C21	0.45436 (12)	0.09801 (18)	0.41902 (10)	0.0490 (4)
H21	0.4606	0.1097	0.4691	0.059*
C22	0.36717 (12)	0.11803 (17)	0.37402 (9)	0.0458 (4)
C23	0.27331 (13)	0.15467 (16)	0.38691 (9)	0.0448 (4)
C24	0.23654 (13)	0.18710 (19)	0.44865 (9)	0.0487 (4)
H24	0.2754	0.1857	0.4943	0.058*
C25	0.14168 (13)	0.22164 (19)	0.44213 (11)	0.0527 (4)
H25	0.1171	0.2433	0.4834	0.063*
C26	0.08358 (13)	0.22374 (19)	0.37386 (10)	0.0523 (4)
H26	0.0201	0.2468	0.3695	0.063*
C27	0.12036 (12)	0.19131 (19)	0.31212 (10)	0.0506 (4)
H27	0.0815	0.1927	0.2664	0.061*
C28	0.21522 (12)	0.15678 (16)	0.31864 (9)	0.0448 (4)
C29	0.23207 (12)	0.12673 (18)	0.18875 (10)	0.0472 (4)
C30	0.23683 (11)	0.00776 (19)	0.13801 (9)	0.0462 (4)
H30	0.2601	−0.0819	0.1486	0.055*
C31	0.19480 (12)	0.06941 (19)	0.06602 (10)	0.0520 (4)
H31	0.1909	0.0190	0.0230	0.062*
C32	0.16284 (13)	0.2012 (2)	0.06608 (10)	0.0522 (4)
H32	0.1326	0.2472	0.0244	0.063*
N1	0.58992 (10)	0.45050 (15)	0.19114 (8)	0.0485 (3)
N2	0.26435 (10)	0.12467 (15)	0.26517 (8)	0.0474 (3)
S1	0.44448 (4)	0.32622 (5)	0.10522 (3)	0.05735 (14)
S2	0.18295 (3)	0.27280 (5)	0.14807 (3)	0.04925 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0430 (9)	0.0521 (10)	0.0493 (10)	−0.0014 (8)	0.0103 (8)	0.0063 (8)
C2	0.0550 (11)	0.0525 (11)	0.0504 (10)	−0.0083 (8)	0.0080 (8)	0.0116 (8)
C3	0.0468 (10)	0.0556 (11)	0.0541 (11)	−0.0092 (8)	0.0139 (8)	0.0104 (9)
C4	0.0483 (10)	0.0566 (11)	0.0669 (12)	−0.0148 (9)	0.0068 (9)	0.0136 (9)
C5	0.0470 (10)	0.0510 (10)	0.0509 (10)	−0.0087 (8)	−0.0109 (8)	0.0109 (8)
C6	0.0436 (10)	0.0505 (10)	0.0493 (10)	−0.0047 (8)	−0.0063 (8)	0.0082 (8)
C7	0.0417 (9)	0.0472 (10)	0.0497 (10)	0.0078 (7)	0.0009 (8)	−0.0004 (8)
C8	0.0611 (12)	0.0503 (11)	0.0543 (11)	0.0072 (9)	−0.0002 (9)	−0.0043 (9)
C9	0.0551 (11)	0.0513 (10)	0.0591 (11)	0.0177 (9)	0.0145 (9)	−0.0086 (9)
C10	0.0494 (10)	0.0579 (11)	0.0565 (11)	0.0104 (9)	0.0106 (8)	0.0058 (9)
C11	0.0545 (11)	0.0531 (11)	0.0552 (11)	0.0009 (9)	0.0097 (9)	0.0028 (9)
C12	0.0432 (9)	0.0464 (9)	0.0437 (9)	0.0021 (7)	0.0042 (7)	−0.0016 (7)
C13	0.0532 (11)	0.0535 (11)	0.0506 (10)	−0.0036 (9)	−0.0102 (8)	−0.0099 (8)
C14	0.0453 (9)	0.0463 (10)	0.0418 (9)	−0.0069 (7)	0.0028 (7)	−0.0079 (7)
C15	0.0508 (11)	0.0561 (11)	0.0653 (12)	−0.0188 (9)	0.0152 (9)	−0.0135 (9)
C16	0.0502 (11)	0.0537 (11)	0.0577 (11)	−0.0153 (9)	0.0081 (9)	−0.0165 (9)
C17	0.0510 (10)	0.0284 (8)	0.0482 (9)	−0.0020 (7)	0.0090 (8)	0.0080 (7)
C18	0.0463 (10)	0.0475 (10)	0.0557 (11)	−0.0032 (8)	0.0106 (8)	0.0046 (8)
C19	0.0548 (11)	0.0571 (11)	0.0465 (10)	0.0114 (9)	0.0166 (8)	0.0084 (8)
C20	0.0501 (11)	0.0657 (12)	0.0470 (10)	0.0090 (9)	0.0042 (8)	0.0149 (9)
C21	0.0503 (10)	0.0445 (9)	0.0490 (10)	0.0020 (8)	0.0005 (8)	0.0069 (8)
C22	0.0542 (10)	0.0345 (8)	0.0469 (9)	−0.0040 (7)	0.0048 (8)	0.0101 (7)
C23	0.0635 (11)	0.0276 (8)	0.0439 (9)	−0.0045 (7)	0.0119 (8)	−0.0024 (7)
C24	0.0535 (11)	0.0554 (11)	0.0399 (9)	−0.0126 (8)	0.0158 (8)	0.0018 (8)
C25	0.0532 (11)	0.0464 (10)	0.0600 (11)	−0.0042 (8)	0.0139 (9)	−0.0044 (8)
C26	0.0523 (11)	0.0565 (10)	0.0499 (10)	−0.0134 (9)	0.0138 (8)	−0.0097 (8)
C27	0.0465 (10)	0.0527 (10)	0.0539 (11)	−0.0106 (8)	0.0126 (8)	−0.0072 (8)
C28	0.0532 (10)	0.0303 (8)	0.0515 (10)	−0.0011 (7)	0.0116 (8)	−0.0006 (7)
C29	0.0502 (10)	0.0431 (9)	0.0494 (10)	0.0099 (8)	0.0118 (8)	0.0140 (7)
C30	0.0322 (8)	0.0503 (10)	0.0541 (10)	0.0011 (7)	0.0030 (7)	0.0012 (8)
C31	0.0471 (10)	0.0538 (11)	0.0555 (11)	−0.0005 (8)	0.0106 (8)	0.0027 (9)
C32	0.0498 (10)	0.0581 (11)	0.0494 (10)	0.0133 (8)	0.0107 (8)	0.0146 (8)
N1	0.0513 (8)	0.0442 (8)	0.0500 (8)	−0.0015 (7)	0.0098 (7)	−0.0030 (6)
N2	0.0490 (8)	0.0439 (8)	0.0501 (8)	0.0089 (6)	0.0112 (7)	0.0135 (6)
S1	0.0547 (3)	0.0552 (3)	0.0540 (3)	−0.0029 (2)	−0.0115 (2)	−0.0119 (2)
S2	0.0514 (3)	0.0445 (2)	0.0527 (3)	0.0103 (2)	0.0120 (2)	0.0151 (2)

Geometric parameters (Å, º) top

C1—N1	1.382 (2)	C17—C18	1.390 (2)
C1—C2	1.390 (2)	C17—C22	1.390 (2)
C1—C6	1.390 (3)	C17—N2	1.399 (2)
C2—C3	1.390 (2)	C18—C19	1.390 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.390 (3)	C19—C20	1.390 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.390 (3)	C20—C21	1.390 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.390 (2)	C21—C22	1.390 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.468 (2)	C22—C23	1.460 (2)
C7—C8	1.390 (2)	C23—C24	1.390 (2)
C7—C12	1.390 (2)	C23—C28	1.390 (2)
C8—C9	1.390 (3)	C24—C25	1.390 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.390 (3)	C25—C26	1.390 (3)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.390 (3)	C26—C27	1.390 (2)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.390 (2)	C27—C28	1.390 (2)
C11—H11	0.9300	C27—H27	0.9300
C12—N1	1.385 (2)	C28—N2	1.361 (2)
C13—N1	1.437 (2)	C29—N2	1.417 (2)
C13—C14	1.519 (3)	C29—C30	1.492 (2)
C13—S1	1.6950 (19)	C29—S2	1.6849 (17)
C14—C15	1.515 (2)	C30—C31	1.491 (2)
C14—H14	0.9300	C30—H30	0.9300
C15—C16	1.339 (3)	C31—C32	1.344 (2)
C15—H15	0.9300	C31—H31	0.9300
C16—S1	1.6638 (19)	C32—S2	1.654 (2)
C16—H16	0.9300	C32—H32	0.9300

N1—C1—C2	129.48 (17)	C19—C18—H18	120.0
N1—C1—C6	110.47 (15)	C17—C18—H18	120.0
C2—C1—C6	120.00 (17)	C18—C19—C20	120.00 (17)
C1—C2—C3	120.00 (18)	C18—C19—H19	120.0
C1—C2—H2	120.0	C20—C19—H19	120.0
C3—C2—H2	120.0	C21—C20—C19	120.00 (17)
C2—C3—C4	120.00 (17)	C21—C20—H20	120.0
C2—C3—H3	120.0	C19—C20—H20	120.0
C4—C3—H3	120.0	C20—C21—C22	120.00 (17)
C5—C4—C3	120.00 (17)	C20—C21—H21	120.0
C5—C4—H4	120.0	C22—C21—H21	120.0
C3—C4—H4	120.0	C21—C22—C17	120.00 (17)
C6—C5—C4	120.00 (18)	C21—C22—C23	134.05 (17)
C6—C5—H5	120.0	C17—C22—C23	105.94 (15)
C4—C5—H5	120.0	C24—C23—C28	120.00 (17)
C5—C6—C1	120.00 (17)	C24—C23—C22	134.21 (17)
C5—C6—C7	134.17 (18)	C28—C23—C22	105.78 (15)
C1—C6—C7	105.77 (15)	C25—C24—C23	120.00 (17)
C8—C7—C12	120.00 (17)	C25—C24—H24	120.0
C8—C7—C6	133.90 (18)	C23—C24—H24	120.0
C12—C7—C6	106.07 (15)	C24—C25—C26	120.00 (18)
C7—C8—C9	120.00 (18)	C24—C25—H25	120.0
C7—C8—H8	120.0	C26—C25—H25	120.0
C9—C8—H8	120.0	C27—C26—C25	120.00 (18)
C8—C9—C10	120.00 (18)	C27—C26—H26	120.0
C8—C9—H9	120.0	C25—C26—H26	120.0
C10—C9—H9	120.0	C28—C27—C26	120.00 (17)
C11—C10—C9	120.00 (18)	C28—C27—H27	120.0
C11—C10—H10	120.0	C26—C27—H27	120.0
C9—C10—H10	120.0	N2—C28—C27	128.75 (16)
C12—C11—C10	120.00 (18)	N2—C28—C23	111.24 (15)
C12—C11—H11	120.0	C27—C28—C23	120.00 (16)
C10—C11—H11	120.0	N2—C29—C30	125.71 (14)
N1—C12—C11	129.82 (17)	N2—C29—S2	119.87 (13)
N1—C12—C7	110.18 (15)	C30—C29—S2	114.42 (13)
C11—C12—C7	120.00 (16)	C31—C30—C29	102.18 (15)
N1—C13—C14	126.32 (15)	C31—C30—H30	128.9
N1—C13—S1	116.91 (14)	C29—C30—H30	128.9
C14—C13—S1	116.74 (12)	C32—C31—C30	116.99 (17)
C15—C14—C13	99.68 (14)	C32—C31—H31	121.5
C15—C14—H14	130.2	C30—C31—H31	121.5
C13—C14—H14	130.2	C31—C32—S2	112.91 (14)
C16—C15—C14	117.26 (17)	C31—C32—H32	123.5
C16—C15—H15	121.4	S2—C32—H32	123.5
C14—C15—H15	121.4	C1—N1—C12	107.48 (14)
C15—C16—S1	114.91 (14)	C1—N1—C13	125.31 (15)
C15—C16—H16	122.5	C12—N1—C13	127.19 (15)
S1—C16—H16	122.5	C28—N2—C17	107.05 (14)
C18—C17—C22	120.00 (16)	C28—N2—C29	128.08 (15)
C18—C17—N2	130.01 (16)	C17—N2—C29	124.64 (15)
C22—C17—N2	109.98 (15)	C16—S1—C13	91.39 (9)
C19—C18—C17	120.00 (17)	C32—S2—C29	93.42 (9)

N1—C1—C2—C3	177.18 (17)	C28—C23—C24—C25	0.0 (2)
C6—C1—C2—C3	0.0 (3)	C22—C23—C24—C25	178.35 (17)
C1—C2—C3—C4	0.0 (3)	C23—C24—C25—C26	0.0 (3)
C2—C3—C4—C5	0.0 (3)	C24—C25—C26—C27	0.0 (3)
C3—C4—C5—C6	0.0 (3)	C25—C26—C27—C28	0.0 (3)
C4—C5—C6—C1	0.0 (3)	C26—C27—C28—N2	−178.69 (17)
C4—C5—C6—C7	−176.78 (18)	C26—C27—C28—C23	0.0 (2)
N1—C1—C6—C5	−177.68 (15)	C24—C23—C28—N2	178.91 (15)
C2—C1—C6—C5	0.0 (3)	C22—C23—C28—N2	0.13 (18)
N1—C1—C6—C7	−0.1 (2)	C24—C23—C28—C27	0.0 (2)
C2—C1—C6—C7	177.60 (16)	C22—C23—C28—C27	−178.77 (15)
C5—C6—C7—C8	−2.1 (3)	N2—C29—C30—C31	−179.27 (16)
C1—C6—C7—C8	−179.20 (19)	S2—C29—C30—C31	0.93 (17)
C5—C6—C7—C12	176.08 (19)	C29—C30—C31—C32	−2.7 (2)
C1—C6—C7—C12	−1.02 (19)	C30—C31—C32—S2	3.4 (2)
C12—C7—C8—C9	0.0 (3)	C2—C1—N1—C12	−176.23 (18)
C6—C7—C8—C9	177.97 (18)	C6—C1—N1—C12	1.2 (2)
C7—C8—C9—C10	0.0 (3)	C2—C1—N1—C13	2.3 (3)
C8—C9—C10—C11	0.0 (3)	C6—C1—N1—C13	179.69 (16)
C9—C10—C11—C12	0.0 (3)	C11—C12—N1—C1	178.44 (18)
C10—C11—C12—N1	179.68 (17)	C7—C12—N1—C1	−1.85 (19)
C10—C11—C12—C7	0.0 (3)	C11—C12—N1—C13	0.0 (3)
C8—C7—C12—N1	−179.74 (16)	C7—C12—N1—C13	179.66 (16)
C6—C7—C12—N1	1.78 (19)	C14—C13—N1—C1	85.2 (2)
C8—C7—C12—C11	0.0 (3)	S1—C13—N1—C1	−92.9 (2)
C6—C7—C12—C11	−178.48 (16)	C14—C13—N1—C12	−96.6 (2)
N1—C13—C14—C15	−178.93 (18)	S1—C13—N1—C12	85.3 (2)
S1—C13—C14—C15	−0.78 (19)	C27—C28—N2—C17	178.81 (17)
C13—C14—C15—C16	1.1 (2)	C23—C28—N2—C17	0.03 (18)
C14—C15—C16—S1	−1.1 (2)	C27—C28—N2—C29	4.2 (3)
C22—C17—C18—C19	0.0 (2)	C23—C28—N2—C29	−174.56 (15)
N2—C17—C18—C19	−179.34 (17)	C18—C17—N2—C28	179.21 (17)
C17—C18—C19—C20	0.0 (3)	C22—C17—N2—C28	−0.19 (17)
C18—C19—C20—C21	0.0 (3)	C18—C17—N2—C29	−6.0 (3)
C19—C20—C21—C22	0.0 (3)	C22—C17—N2—C29	174.63 (15)
C20—C21—C22—C17	0.0 (2)	C30—C29—N2—C28	−125.31 (19)
C20—C21—C22—C23	178.93 (18)	S2—C29—N2—C28	54.5 (2)
C18—C17—C22—C21	0.0 (2)	C30—C29—N2—C17	61.0 (2)
N2—C17—C22—C21	179.46 (15)	S2—C29—N2—C17	−119.22 (16)
C18—C17—C22—C23	−179.20 (14)	C15—C16—S1—C13	0.45 (17)
N2—C17—C22—C23	0.27 (17)	N1—C13—S1—C16	178.60 (16)
C21—C22—C23—C24	2.2 (3)	C14—C13—S1—C16	0.28 (16)
C17—C22—C23—C24	−178.76 (17)	C31—C32—S2—C29	−2.25 (16)
C21—C22—C23—C28	−179.28 (18)	N2—C29—S2—C32	−179.18 (15)
C17—C22—C23—C28	−0.24 (17)	C30—C29—S2—C32	0.64 (14)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NS
M_r	249.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.412 (3), 9.5831 (19), 18.671 (4)
β (°)	100.64 (3)
V (Å³)	2534.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.94, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	26852, 4980, 4138
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.080, 1.13
No. of reflections	4980
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

References

Bruker (2000). CAD-4 EXPRESS. SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, I.-Y., Lin, J. T., Tao, Y.-T., Balasubramaniam, E., Su, Y. Z. & Ko, C.-W. (2001). Chem. Mater. 13, 2626–2631. Web of Science CrossRef CAS Google Scholar