10-(1,3-Benzothia-zol-2-yl)-1,1,7,7-tetra-methyl-2,3,6,7-tetra-hydro-1H,5H,11H-pyrano[3,2-g]pyrido[3,2,1-hi]quinoline.

In the title compound, C(26)H(26)N(2)O(2)S, the dihedral angle between the benzothia-zole and coumarin rings is 8.34 (7)°, indicating that the overall benzothia-zole substituent is almost coplanar with the coumarin rings. An intra-molecular S⋯O [2.813 (1) Å] contact may help to stabilize the mol-ecular conformation. In the crystal structure, π-π stacking inter-actions [centroid-centroid distances = 3.480 (2) Å] link pairs of mol-ecules.

Related literature

For background to organic light-emitting diodes (OLEDs), see: Lee et al. (2009 ▶). For the use of the title compound as an organic light-emitting diode, see: White et al.(2010 ▶). For S⋯O inter­actions, see: Mellor et al. (1971 ▶); Kucsman et al. (1984 ▶). For the crystal structure of benzothia­zole-ethyl­coumarin, see: Padilla-Martínez et al. (2003 ▶) and for that of coumarin, see: Gavuzzo et al. (1974 ▶); Chinnakali et al. (1999 ▶).

Experimental

Crystal data

C26H26N2O2S

M = 430.55

Monoclinic,

a = 9.2180 (4) Å

b = 13.7079 (6) Å

c = 18.6885 (6) Å

β = 115.890 (2)°

V = 2124.46 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 173 K

0.50 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

11820 measured reflections

4179 independent reflections

3592 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.06

4179 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; 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/S1600536810011086/sj2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011086/sj2754Isup2.hkl

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

C26H26N2O2S	F(000) = 912
Mr = 430.55	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7330 reflections
a = 9.2180 (4) Å	θ = 2.4–28.3°
b = 13.7079 (6) Å	µ = 0.18 mm−1
c = 18.6885 (6) Å	T = 173 K
β = 115.890 (2)°	Block, orange
V = 2124.46 (15) Å3	0.50 × 0.40 × 0.40 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −11→9
11820 measured reflections	k = −12→16
4179 independent reflections	l = −20→23

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) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.044P)2 + 1.0847P] where P = (Fo2 + 2Fc2)/3
4179 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.19362 (5)	0.61269 (3)	0.29844 (2)	0.02617 (12)
O1	0.48027 (14)	0.50800 (9)	0.33612 (7)	0.0319 (3)
O2	0.57724 (12)	0.38158 (8)	0.41606 (6)	0.0239 (2)
N1	0.06477 (15)	0.51630 (9)	0.37615 (8)	0.0241 (3)
N2	0.79705 (17)	0.09754 (10)	0.57717 (8)	0.0288 (3)
C1	−0.0975 (2)	0.72222 (13)	0.23952 (10)	0.0329 (4)
H1	−0.0649	0.7633	0.2083	0.039*
C2	−0.2464 (2)	0.73381 (13)	0.23991 (11)	0.0362 (4)
H2	−0.3164	0.7841	0.2088	0.043*
C3	−0.2958 (2)	0.67300 (13)	0.28511 (10)	0.0311 (4)
H3	−0.3993	0.6820	0.2836	0.037*
C4	−0.19676 (19)	0.60012 (12)	0.33190 (10)	0.0272 (3)
H4	−0.2305	0.5594	0.3630	0.033*
C5	−0.04516 (18)	0.58726 (11)	0.33269 (9)	0.0236 (3)
C6	0.19373 (18)	0.52131 (11)	0.36444 (9)	0.0214 (3)
C7	0.00332 (19)	0.64804 (12)	0.28657 (9)	0.0252 (3)
C8	0.32875 (18)	0.45412 (11)	0.40379 (9)	0.0217 (3)
C9	0.32966 (18)	0.38973 (11)	0.45990 (9)	0.0232 (3)
H9	0.2454	0.3929	0.4761	0.028*
C10	0.45101 (18)	0.31905 (11)	0.49446 (9)	0.0218 (3)
C11	0.57626 (18)	0.31438 (11)	0.47106 (9)	0.0210 (3)
C12	0.46105 (18)	0.45318 (11)	0.38203 (9)	0.0228 (3)
C13	0.44984 (18)	0.24849 (11)	0.54910 (9)	0.0233 (3)
H13	0.3675	0.2512	0.5666	0.028*
C14	0.56330 (18)	0.17633 (11)	0.57769 (9)	0.0219 (3)
C15	0.68816 (18)	0.17229 (11)	0.55131 (9)	0.0219 (3)
C16	0.69810 (18)	0.24492 (11)	0.49835 (9)	0.0214 (3)
C17	0.56258 (19)	0.10207 (11)	0.63862 (9)	0.0243 (3)
C18	0.6185 (2)	0.00427 (12)	0.61992 (10)	0.0316 (4)
H18A	0.6225	−0.0449	0.6596	0.038*
H18B	0.5397	−0.0184	0.5668	0.038*
C19	0.7820 (3)	0.01276 (14)	0.62120 (12)	0.0402 (5)
H19A	0.8645	0.0174	0.6771	0.048*
H19B	0.8040	−0.0472	0.5980	0.048*
C20	0.9368 (2)	0.09144 (14)	0.56085 (11)	0.0352 (4)
H20A	0.9156	0.0432	0.5180	0.042*
H20B	1.0305	0.0683	0.6091	0.042*
C21	0.9768 (2)	0.18838 (13)	0.53606 (10)	0.0312 (4)
H21A	1.0613	0.1787	0.5176	0.037*
H21B	1.0210	0.2322	0.5828	0.037*
C22	0.82998 (18)	0.23758 (11)	0.46957 (9)	0.0237 (3)
C23	0.6774 (2)	0.13677 (13)	0.72253 (10)	0.0342 (4)
H23A	0.7856	0.1461	0.7258	0.051*
H23B	0.6817	0.0877	0.7616	0.051*
H23C	0.6383	0.1987	0.7338	0.051*
C24	0.3950 (2)	0.08820 (13)	0.63537 (11)	0.0342 (4)
H24A	0.3197	0.0660	0.5821	0.051*
H24B	0.3572	0.1503	0.6471	0.051*
H24D	0.4006	0.0394	0.6748	0.051*
C25	0.7662 (2)	0.17553 (14)	0.39363 (10)	0.0357 (4)
H25A	0.6727	0.2079	0.3519	0.054*
H25D	0.7340	0.1112	0.4046	0.054*
H25B	0.8510	0.1678	0.3758	0.054*
C26	0.8916 (2)	0.33538 (12)	0.45338 (10)	0.0302 (4)
H26D	0.8026	0.3703	0.4111	0.045*
H26A	0.9772	0.3233	0.4367	0.045*
H26B	0.9345	0.3749	0.5020	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0285 (2)	0.0226 (2)	0.0269 (2)	0.00232 (16)	0.01166 (17)	0.00763 (15)
O1	0.0331 (6)	0.0313 (6)	0.0365 (6)	0.0063 (5)	0.0199 (5)	0.0135 (5)
O2	0.0244 (5)	0.0235 (6)	0.0255 (5)	0.0046 (4)	0.0126 (5)	0.0070 (4)
N1	0.0239 (7)	0.0215 (7)	0.0263 (7)	0.0020 (5)	0.0104 (5)	0.0026 (5)
N2	0.0340 (8)	0.0252 (7)	0.0295 (7)	0.0102 (6)	0.0158 (6)	0.0076 (6)
C1	0.0364 (9)	0.0253 (8)	0.0299 (9)	0.0046 (7)	0.0079 (7)	0.0064 (7)
C2	0.0345 (9)	0.0279 (9)	0.0331 (9)	0.0109 (7)	0.0027 (7)	0.0026 (7)
C3	0.0247 (8)	0.0291 (9)	0.0316 (9)	0.0057 (7)	0.0048 (7)	−0.0065 (7)
C4	0.0255 (8)	0.0239 (8)	0.0289 (8)	0.0000 (6)	0.0088 (7)	−0.0042 (6)
C5	0.0256 (8)	0.0182 (7)	0.0221 (7)	0.0015 (6)	0.0059 (6)	−0.0019 (6)
C6	0.0254 (8)	0.0171 (7)	0.0206 (7)	−0.0004 (6)	0.0090 (6)	0.0008 (6)
C7	0.0262 (8)	0.0218 (8)	0.0234 (7)	0.0007 (6)	0.0072 (6)	−0.0017 (6)
C8	0.0227 (7)	0.0189 (7)	0.0225 (7)	0.0002 (6)	0.0089 (6)	0.0004 (6)
C9	0.0223 (7)	0.0233 (8)	0.0249 (8)	−0.0001 (6)	0.0111 (6)	0.0011 (6)
C10	0.0224 (7)	0.0209 (7)	0.0222 (7)	0.0006 (6)	0.0097 (6)	0.0017 (6)
C11	0.0240 (7)	0.0192 (7)	0.0183 (7)	−0.0015 (6)	0.0077 (6)	0.0004 (6)
C12	0.0236 (8)	0.0211 (8)	0.0218 (7)	0.0005 (6)	0.0083 (6)	0.0018 (6)
C13	0.0242 (8)	0.0241 (8)	0.0228 (7)	−0.0005 (6)	0.0114 (6)	0.0015 (6)
C14	0.0261 (8)	0.0191 (7)	0.0191 (7)	−0.0014 (6)	0.0085 (6)	−0.0001 (6)
C15	0.0248 (8)	0.0193 (7)	0.0182 (7)	0.0015 (6)	0.0062 (6)	−0.0011 (6)
C16	0.0222 (7)	0.0210 (7)	0.0190 (7)	−0.0001 (6)	0.0073 (6)	−0.0020 (6)
C17	0.0310 (8)	0.0207 (8)	0.0204 (7)	0.0005 (6)	0.0104 (6)	0.0029 (6)
C18	0.0489 (11)	0.0204 (8)	0.0282 (8)	0.0052 (7)	0.0195 (8)	0.0059 (7)
C19	0.0569 (12)	0.0296 (9)	0.0432 (10)	0.0196 (9)	0.0304 (9)	0.0164 (8)
C20	0.0344 (9)	0.0367 (10)	0.0380 (10)	0.0154 (8)	0.0190 (8)	0.0092 (8)
C21	0.0263 (8)	0.0351 (9)	0.0316 (9)	0.0071 (7)	0.0121 (7)	0.0031 (7)
C22	0.0238 (8)	0.0244 (8)	0.0230 (7)	0.0019 (6)	0.0102 (6)	−0.0004 (6)
C23	0.0467 (10)	0.0284 (9)	0.0219 (8)	−0.0023 (8)	0.0098 (7)	0.0022 (7)
C24	0.0395 (10)	0.0278 (9)	0.0390 (10)	−0.0006 (8)	0.0205 (8)	0.0098 (7)
C25	0.0412 (10)	0.0386 (10)	0.0301 (9)	−0.0010 (8)	0.0181 (8)	−0.0075 (8)
C26	0.0242 (8)	0.0319 (9)	0.0359 (9)	−0.0005 (7)	0.0144 (7)	0.0033 (7)

S1—C7	1.7382 (16)	C14—C17	1.530 (2)
S1—C6	1.7576 (15)	C15—C16	1.435 (2)
O1—C12	1.2104 (18)	C16—C22	1.532 (2)
O2—C11	1.3832 (18)	C17—C18	1.530 (2)
O2—C12	1.3857 (18)	C17—C24	1.531 (2)
N1—C6	1.301 (2)	C17—C23	1.535 (2)
N1—C5	1.383 (2)	C18—C19	1.501 (3)
N2—C15	1.367 (2)	C18—H18A	0.9900
N2—C20	1.450 (2)	C18—H18B	0.9900
N2—C19	1.465 (2)	C19—H19A	0.9900
C1—C2	1.385 (3)	C19—H19B	0.9900
C1—C7	1.399 (2)	C20—C21	1.505 (3)
C1—H1	0.9500	C20—H20A	0.9900
C2—C3	1.397 (3)	C20—H20B	0.9900
C2—H2	0.9500	C21—C22	1.537 (2)
C3—C4	1.378 (2)	C21—H21A	0.9900
C3—H3	0.9500	C21—H21B	0.9900
C4—C5	1.402 (2)	C22—C25	1.535 (2)
C4—H4	0.9500	C22—C26	1.537 (2)
C5—C7	1.405 (2)	C23—H23A	0.9800
C6—C8	1.463 (2)	C23—H23B	0.9800
C8—C9	1.368 (2)	C23—H23C	0.9800
C8—C12	1.444 (2)	C24—H24A	0.9800
C9—C10	1.406 (2)	C24—H24B	0.9800
C9—H9	0.9500	C24—H24D	0.9800
C10—C11	1.403 (2)	C25—H25A	0.9800
C10—C13	1.410 (2)	C25—H25D	0.9800
C11—C16	1.389 (2)	C25—H25B	0.9800
C13—C14	1.367 (2)	C26—H26D	0.9800
C13—H13	0.9500	C26—H26A	0.9800
C14—C15	1.438 (2)	C26—H26B	0.9800
C7—S1—C6	88.83 (7)	C14—C17—C23	109.21 (13)
C11—O2—C12	123.93 (12)	C18—C17—C23	110.73 (14)
C6—N1—C5	110.66 (13)	C24—C17—C23	108.23 (14)
C15—N2—C20	123.48 (14)	C19—C18—C17	111.36 (14)
C15—N2—C19	123.93 (14)	C19—C18—H18A	109.4
C20—N2—C19	112.54 (13)	C17—C18—H18A	109.4
C2—C1—C7	117.92 (16)	C19—C18—H18B	109.4
C2—C1—H1	121.0	C17—C18—H18B	109.4
C7—C1—H1	121.0	H18A—C18—H18B	108.0
C1—C2—C3	121.35 (16)	N2—C19—C18	113.16 (14)
C1—C2—H2	119.3	N2—C19—H19A	108.9
C3—C2—H2	119.3	C18—C19—H19A	108.9
C4—C3—C2	121.03 (16)	N2—C19—H19B	108.9
C4—C3—H3	119.5	C18—C19—H19B	108.9
C2—C3—H3	119.5	H19A—C19—H19B	107.8
C3—C4—C5	118.62 (16)	N2—C20—C21	111.93 (14)
C3—C4—H4	120.7	N2—C20—H20A	109.2
C5—C4—H4	120.7	C21—C20—H20A	109.2
N1—C5—C4	124.45 (14)	N2—C20—H20B	109.2
N1—C5—C7	115.44 (14)	C21—C20—H20B	109.2
C4—C5—C7	120.11 (14)	H20A—C20—H20B	107.9
N1—C6—C8	121.43 (13)	C20—C21—C22	112.88 (14)
N1—C6—S1	115.79 (11)	C20—C21—H21A	109.0
C8—C6—S1	122.77 (11)	C22—C21—H21A	109.0
C1—C7—C5	120.97 (15)	C20—C21—H21B	109.0
C1—C7—S1	129.75 (14)	C22—C21—H21B	109.0
C5—C7—S1	109.27 (11)	H21A—C21—H21B	107.8
C9—C8—C12	119.13 (14)	C16—C22—C25	108.57 (13)
C9—C8—C6	120.73 (14)	C16—C22—C21	107.36 (12)
C12—C8—C6	120.12 (13)	C25—C22—C21	110.56 (14)
C8—C9—C10	122.29 (14)	C16—C22—C26	115.48 (13)
C8—C9—H9	118.9	C25—C22—C26	109.08 (13)
C10—C9—H9	118.9	C21—C22—C26	105.74 (13)
C11—C10—C9	119.09 (14)	C17—C23—H23A	109.5
C11—C10—C13	117.51 (14)	C17—C23—H23B	109.5
C9—C10—C13	123.32 (14)	H23A—C23—H23B	109.5
O2—C11—C16	117.57 (13)	C17—C23—H23C	109.5
O2—C11—C10	118.32 (13)	H23A—C23—H23C	109.5
C16—C11—C10	124.09 (14)	H23B—C23—H23C	109.5
O1—C12—O2	116.23 (13)	C17—C24—H24A	109.5
O1—C12—C8	126.66 (14)	C17—C24—H24B	109.5
O2—C12—C8	117.11 (13)	H24A—C24—H24B	109.5
C14—C13—C10	122.20 (14)	C17—C24—H24D	109.5
C14—C13—H13	118.9	H24A—C24—H24D	109.5
C10—C13—H13	118.9	H24B—C24—H24D	109.5
C13—C14—C15	118.95 (14)	C22—C25—H25A	109.5
C13—C14—C17	121.41 (14)	C22—C25—H25D	109.5
C15—C14—C17	119.61 (13)	H25A—C25—H25D	109.5
N2—C15—C16	120.40 (14)	C22—C25—H25B	109.5
N2—C15—C14	118.82 (14)	H25A—C25—H25B	109.5
C16—C15—C14	120.78 (13)	H25D—C25—H25B	109.5
C11—C16—C15	116.37 (13)	C22—C26—H26D	109.5
C11—C16—C22	123.68 (13)	C22—C26—H26A	109.5
C15—C16—C22	119.74 (13)	H26D—C26—H26A	109.5
C14—C17—C18	107.56 (12)	C22—C26—H26B	109.5
C14—C17—C24	112.67 (13)	H26D—C26—H26B	109.5
C18—C17—C24	108.46 (14)	H26A—C26—H26B	109.5
C7—C1—C2—C3	−0.6 (3)	C10—C13—C14—C17	178.36 (14)
C1—C2—C3—C4	1.0 (3)	C20—N2—C15—C16	6.7 (2)
C2—C3—C4—C5	−0.7 (2)	C19—N2—C15—C16	−170.41 (16)
C6—N1—C5—C4	179.25 (15)	C20—N2—C15—C14	−173.69 (15)
C6—N1—C5—C7	−0.07 (19)	C19—N2—C15—C14	9.2 (2)
C3—C4—C5—N1	−179.17 (15)	C13—C14—C15—N2	−177.07 (14)
C3—C4—C5—C7	0.1 (2)	C17—C14—C15—N2	4.7 (2)
C5—N1—C6—C8	179.91 (13)	C13—C14—C15—C16	2.5 (2)
C5—N1—C6—S1	−0.49 (17)	C17—C14—C15—C16	−175.77 (13)
C7—S1—C6—N1	0.69 (13)	O2—C11—C16—C15	−176.04 (12)
C7—S1—C6—C8	−179.71 (13)	C10—C11—C16—C15	2.5 (2)
C2—C1—C7—C5	0.0 (2)	O2—C11—C16—C22	−1.4 (2)
C2—C1—C7—S1	178.80 (13)	C10—C11—C16—C22	177.11 (14)
N1—C5—C7—C1	179.56 (14)	N2—C15—C16—C11	175.88 (14)
C4—C5—C7—C1	0.2 (2)	C14—C15—C16—C11	−3.7 (2)
N1—C5—C7—S1	0.57 (17)	N2—C15—C16—C22	1.0 (2)
C4—C5—C7—S1	−178.78 (12)	C14—C15—C16—C22	−178.56 (13)
C6—S1—C7—C1	−179.54 (16)	C13—C14—C17—C18	144.64 (15)
C6—S1—C7—C5	−0.66 (12)	C15—C14—C17—C18	−37.13 (19)
N1—C6—C8—C9	−6.1 (2)	C13—C14—C17—C24	25.2 (2)
S1—C6—C8—C9	174.29 (12)	C15—C14—C17—C24	−156.60 (14)
N1—C6—C8—C12	172.08 (14)	C13—C14—C17—C23	−95.14 (17)
S1—C6—C8—C12	−7.5 (2)	C15—C14—C17—C23	83.09 (17)
C12—C8—C9—C10	−3.3 (2)	C14—C17—C18—C19	57.26 (18)
C6—C8—C9—C10	174.95 (14)	C24—C17—C18—C19	179.38 (14)
C8—C9—C10—C11	0.3 (2)	C23—C17—C18—C19	−62.00 (18)
C8—C9—C10—C13	−176.38 (15)	C15—N2—C19—C18	12.7 (2)
C12—O2—C11—C16	178.12 (13)	C20—N2—C19—C18	−164.74 (16)
C12—O2—C11—C10	−0.5 (2)	C17—C18—C19—N2	−46.8 (2)
C9—C10—C11—O2	1.6 (2)	C15—N2—C20—C21	18.0 (2)
C13—C10—C11—O2	178.49 (13)	C19—N2—C20—C21	−164.59 (16)
C9—C10—C11—C16	−176.89 (14)	N2—C20—C21—C22	−50.0 (2)
C13—C10—C11—C16	0.0 (2)	C11—C16—C22—C25	−85.78 (18)
C11—O2—C12—O1	178.43 (14)	C15—C16—C22—C25	88.70 (17)
C11—O2—C12—C8	−2.4 (2)	C11—C16—C22—C21	154.67 (14)
C9—C8—C12—O1	−176.73 (16)	C15—C16—C22—C21	−30.85 (18)
C6—C8—C12—O1	5.0 (2)	C11—C16—C22—C26	37.0 (2)
C9—C8—C12—O2	4.2 (2)	C15—C16—C22—C26	−148.48 (14)
C6—C8—C12—O2	−174.01 (13)	C20—C21—C22—C16	54.98 (18)
C11—C10—C13—C14	−1.4 (2)	C20—C21—C22—C25	−63.29 (18)
C9—C10—C13—C14	175.38 (15)	C20—C21—C22—C26	178.78 (14)
C10—C13—C14—C15	0.1 (2)