Crystal structure of 5-[bis­(4-eth­oxy­phenyl)amino]­thio­phene-2-carbaldehyde

Tan, J.-Y.; Kong, M.; Wu, J.-Y.

doi:10.1107/S1600536814018984

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1075-o1076

doi:10.1107/S1600536814018984

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Crystal structure of 5-[bis(4-ethoxyphenyl)amino]thiophene-2-carbaldehyde

Jing-Yun Tan,^a,^b Ming Kong ^a,^b and Jie-Ying Wu ^a,^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: jywu1957@163.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 16 August 2014; accepted 22 August 2014; online 30 August 2014)

In the title compound, C₂₁H₂₁NO₃S, the planes of the two benzene rings are nearly perpendicular to one another [dihedral angle = 84.50 (10)°] and they are oriented with respect to the plane of the thiophene ring at dihedral angles of 59.15 (9) and 66.61 (9)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming supramolecular chains propagating along the b-axis direction.

Keywords: crystal structure; thiophene-2-carbaldehyde; hydrogen bonding; supramolecular chains.

CCDC reference: 1016303

1. Related literature

For applications of thiophene derivatives, see: Justin Thomas et al. (2008 ); Hansel et al. (2003 ); Mazzeo et al. (2003 ); Zhan et al. (2007 ); Bedworth et al. (1996 ); Raposo et al. (2011 ); Takekuma et al. (2005 ); Wurthner et al. (2002 ). For a related structure, see: Li et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₁H₂₁NO₃S
M_r = 367.45
Monoclinic, P 2₁ /c
a = 11.101 (3) Å
b = 10.457 (3) Å
c = 17.326 (5) Å
β = 104.473 (4)°
V = 1947.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

2.1.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Bruker, 2002 ) T_min = 0.946, T_max = 0.964
13574 measured reflections
3430 independent reflections
2596 reflections with I > 2σ(I)
R_int = 0.031

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.134
S = 0.93
3430 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.97	2.55	3.470 (3)	159
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1016303

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814018984/xu5814sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018984/xu5814Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018984/xu5814Isup3.cml

checkCIF report

Comment top

Due to the outstanding electronic tenability and considerable chemical and environmental stability, thiophene derivatives have been widely used in solar cells (Justin Thomas et al., 2008; Hansel et al., 2003), organic light-emitting diodes (OLEDs) (Mazzeo et al., 2003), organic field-effect transistors (OFETs) (Zhan et al., 2007) and NLO devices (Bedworth et al., 1996; Raposo et al., 2011). Among them, the research of thiophene carboxaldehyde, which is an extremely important intermediate, is abundant (Takekuma et al., 2005; Wurthner et al., 2002). In this paper, a novel thiophene carboxaldehyde derivative, 5-(bis(4-ethoxyphenyl)amino)thiophene-2-carbaldehyde (Fig.1), was synthesized.

It possesses typical propeller structure, just the same with other triarylamine. The carbonyl group is coplanar with the thiophene ring, which indicates well conjugation. As shown in Fig.2, for the existence of intermolecular C2—H2A···O3 hydrogen bond, the one-dimensional linear chain structure was formed along b axis.

Related literature top

For applications of thiophene derivatives, see: Justin Thomas et al. (2008); Hansel et al. (2003); Mazzeo et al. (2003); Zhan et al. (2007); Bedworth et al. (1996); Raposo et al. (2011); Takekuma et al. (2005); Wurthner et al. (2002). For a related structure, see: Li et al. (2013).

Experimental top

The intermediate bis(4-ethoxyphenyl)amine was synthesized according to following procedure. Cuprous iodide (0.95 g, 5 mmol), L-Proline (1.15 g, 10 mmol) and anhydrous potassium carbonate (13.8 g, 100 mmol) were placed in an oven-dried 250 ml Schlenk flask. The reaction vessel was evacuated and filled with prepurified argon, a process which was repeated three times. Then refined dimethylsulfoxide (100 ml) was added with a syringe under a counterflow of argon. After that, 4-Iodophenetole (12.5 g, 50 mmol), Phenetidine (8.23 g, 60 mmol) and a particle of 18-Crown-6 (0.1981 g, 0.75 mmol) were added. The reaction was stirred at 90 degrees celsius for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature. The mixture was filtered through a Buchner funnel to remove the deposition. Then diluted with water (500 ml) and stirred for one day. A kind of grey educt were obtained after separate the water by a Buchner funnel again. Purification of the residue by column chromatography on silica gel (petroleum ether/ethyl acetate = 40:1) gave bis(4-ethoxyphenyl)amine as white powder, with yield of 41.3%. M.p.= 89 degrees celsius. ¹H NMR: (400 MHz, DMSO-d₆), d(p.p.m.): 1.33 (t, 6H), 3.93 (q,4H), 5.61 (s, 1H), 6.80 (d, 4H), 6.96 (d, 4H).

The synthesis of the title compound. Phenanthroline (0.45 g, 2.3 mmol), cuprous iodide (0.46 g, 2.4 mmol), anhydrous potassium carbonate (5.00 g, 36 mmol) and bis(4-ethoxyphenyl)amine (3.09 g, 12 mmol) were placed in an oven-dried 250 ml Schlenk flask. The reaction vessel was evacuated and filled with prepurified argon, a process which was repeated three times. Then refined dimethylsulfoxide (120 ml) and 1.90 g 5-Bromo-2-thiophenecarbalde-hyde (10 mmol) were added with a syringe under a counterflow of argon. At last, a particle of 18-Crown-6 (0.0396 g, 0.15 mmol) and two drops of Aliquat336 (0.0200 g, 0.05 mmol) were added. The reaction was stirred at 90 degrees celsius for 48 h. Upon completion of the reaction, the mixture was cooled to room temperature. The mixture was filtered through a Buchner funnel to remove the deposition. Then diluted with water (500 ml) and stirred for one day. A kind of yellowish-brown educt were obtained after separate the water by a Buchner funnel again. Purification of the residue by column chromatography on silica gel (Petroleum/Ethyl Acetate = 20:1) gave title compound as yellowish-brown particle, with yield of 45%. m.p.= 101 degrees celsius. ¹H NMR: (400 MHz, d-chloroform), d(p.p.m.): 1.42 (t, 6H), 4.04 (q, 4H), 6.17 (d,1H), 6.88 (d, 4H), 7.22 (d, 4H), 7.41 (d, 1H), 9.53 (s, 1H). ¹³C NMR(150 MHz, d₆-acetone): d(p.p.m.): 14.81, 63.77, 109.09, 115.54, 127.17, 127.99, 128.55, 138.71, 157.39, 166.42, 180.95. IR (KBr, cm^-1): 3058 (w), 2976 (m), 2931 (w), 2895 (w), 2790 (w), 1627 (s), 1508 (s), 1443 (vs), 1420 (m), 1392 (m), 1353 (m), 1244 (s), 1175 (m), 1054 (m), 824 (m).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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, with atom labels and 50% probability displacement ellipsoids for non-H atoms
	Fig. 2. The infinite one-dimensional linear chain structure.

5-[Bis(4-Ethoxyphenyl)amino]thiophene-2-carbaldehyde top

Crystal data top

C₂₁H₂₁NO₃S	F(000) = 776
M_r = 367.45	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 374 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.101 (3) Å	Cell parameters from 3509 reflections
b = 10.457 (3) Å	θ = 2.3–24.1°
c = 17.326 (5) Å	µ = 0.19 mm⁻¹
β = 104.473 (4)°	T = 296 K
V = 1947.5 (10) Å³	Block, brown
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Radiation source: fine-focus sealed tube	2596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: ψ scan (SADABS; Bruker, 2002)	h = −13→13
T_min = 0.946, T_max = 0.964	k = −12→12
13574 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3430 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₂₁NO₃S	V = 1947.5 (10) Å³
M_r = 367.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.101 (3) Å	µ = 0.19 mm⁻¹
b = 10.457 (3) Å	T = 296 K
c = 17.326 (5) Å	0.30 × 0.20 × 0.20 mm
β = 104.473 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Absorption correction: ψ scan (SADABS; Bruker, 2002)	2596 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.964	R_int = 0.031
13574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 0.93	Δρ_max = 0.15 e Å⁻³
3430 reflections	Δρ_min = −0.21 e Å⁻³
237 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	0.4645 (2)	0.2539 (2)	−0.07326 (14)	0.0795 (8)
H1A	0.3875	0.2164	−0.1023	0.119*
H1B	0.5294	0.1910	−0.0652	0.119*
H1C	0.4851	0.3245	−0.1030	0.119*
C2	0.4511 (2)	0.3002 (2)	0.00542 (12)	0.0613 (6)
H2A	0.4353	0.2288	0.0373	0.074*
H2B	0.5269	0.3425	0.0341	0.074*
C3	0.32106 (17)	0.44336 (17)	0.05611 (10)	0.0441 (4)
C4	0.22779 (19)	0.53578 (19)	0.04076 (11)	0.0528 (5)
H4	0.1875	0.5558	−0.0116	0.063*
C5	0.19465 (19)	0.59780 (19)	0.10249 (11)	0.0507 (5)
H5	0.1314	0.6585	0.0919	0.061*
C6	0.37954 (18)	0.41280 (18)	0.13421 (10)	0.0455 (5)
H6	0.4409	0.3502	0.1451	0.055*
C7	0.34628 (16)	0.47574 (18)	0.19585 (10)	0.0430 (4)
H7	0.3853	0.4547	0.2483	0.052*
C8	0.25621 (17)	0.56915 (17)	0.18073 (10)	0.0412 (4)
C9	0.0530 (2)	0.2588 (2)	0.59350 (13)	0.0724 (7)
H9A	−0.0314	0.2883	0.5840	0.109*
H9B	0.0908	0.2592	0.6497	0.109*
H9C	0.0537	0.1733	0.5733	0.109*
C10	0.1249 (2)	0.3460 (2)	0.55176 (12)	0.0575 (6)
H10A	0.1263	0.4323	0.5725	0.069*
H10B	0.2100	0.3163	0.5602	0.069*
C11	0.11284 (18)	0.4174 (2)	0.41918 (11)	0.0499 (5)
C12	0.21873 (17)	0.49193 (19)	0.44138 (11)	0.0514 (5)
H12	0.2638	0.4942	0.4944	0.062*
C13	0.25766 (17)	0.56310 (19)	0.38494 (11)	0.0486 (5)
H13	0.3301	0.6115	0.4000	0.058*
C14	0.0478 (2)	0.4155 (2)	0.34026 (12)	0.0660 (7)
H14	−0.0225	0.3642	0.3245	0.079*
C15	0.08529 (19)	0.4883 (2)	0.28423 (11)	0.0586 (6)
H15	0.0396	0.4870	0.2313	0.070*
C16	0.19027 (17)	0.56314 (18)	0.30648 (10)	0.0427 (5)
C17	0.25459 (15)	0.76413 (19)	0.25697 (9)	0.0397 (4)
C18	0.22906 (18)	0.84674 (18)	0.31280 (11)	0.0460 (5)
H18	0.1903	0.8222	0.3522	0.055*
C19	0.26784 (18)	0.97091 (18)	0.30347 (11)	0.0499 (5)
H19	0.2577	1.0379	0.3366	0.060*
C20	0.32226 (17)	0.98624 (18)	0.24143 (10)	0.0462 (5)
C21	0.3744 (2)	1.0975 (2)	0.21472 (12)	0.0575 (5)
H21	0.3685	1.1741	0.2408	0.069*
N1	0.22787 (14)	0.63697 (15)	0.24656 (8)	0.0450 (4)
O1	0.34853 (14)	0.38830 (14)	−0.00900 (7)	0.0573 (4)
O2	0.06415 (13)	0.34394 (14)	0.46905 (8)	0.0646 (4)
O3	0.42616 (15)	1.09978 (15)	0.16028 (9)	0.0707 (5)
S1	0.32839 (5)	0.84196 (5)	0.19335 (3)	0.0468 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.109 (2)	0.0737 (17)	0.0733 (15)	0.0184 (15)	0.0560 (15)	0.0055 (13)
C2	0.0756 (15)	0.0578 (13)	0.0612 (13)	0.0155 (12)	0.0369 (11)	0.0063 (11)
C3	0.0560 (12)	0.0403 (10)	0.0406 (9)	−0.0024 (9)	0.0208 (9)	−0.0021 (8)
C4	0.0657 (13)	0.0565 (13)	0.0369 (9)	0.0115 (10)	0.0142 (9)	0.0030 (9)
C5	0.0577 (12)	0.0504 (12)	0.0446 (10)	0.0109 (10)	0.0143 (9)	0.0024 (9)
C6	0.0505 (11)	0.0409 (11)	0.0479 (11)	0.0044 (9)	0.0176 (9)	0.0057 (8)
C7	0.0510 (11)	0.0421 (11)	0.0377 (9)	−0.0011 (9)	0.0143 (8)	0.0033 (8)
C8	0.0492 (11)	0.0393 (10)	0.0394 (9)	−0.0047 (8)	0.0192 (8)	−0.0039 (8)
C9	0.0796 (16)	0.0772 (17)	0.0695 (15)	0.0054 (13)	0.0353 (13)	0.0250 (13)
C10	0.0575 (13)	0.0674 (15)	0.0503 (12)	0.0064 (11)	0.0184 (10)	0.0179 (10)
C11	0.0493 (12)	0.0556 (13)	0.0482 (11)	−0.0079 (9)	0.0186 (9)	0.0051 (9)
C12	0.0481 (11)	0.0600 (13)	0.0435 (10)	−0.0046 (10)	0.0066 (9)	0.0085 (9)
C13	0.0437 (11)	0.0526 (12)	0.0490 (11)	−0.0091 (9)	0.0108 (9)	0.0030 (9)
C14	0.0627 (14)	0.0834 (18)	0.0522 (12)	−0.0346 (12)	0.0149 (10)	0.0007 (11)
C15	0.0595 (13)	0.0761 (15)	0.0400 (10)	−0.0205 (11)	0.0120 (9)	−0.0005 (10)
C16	0.0483 (11)	0.0436 (11)	0.0406 (9)	−0.0028 (8)	0.0192 (8)	−0.0010 (8)
C17	0.0399 (10)	0.0442 (11)	0.0361 (9)	0.0000 (8)	0.0118 (8)	0.0005 (8)
C18	0.0537 (12)	0.0484 (12)	0.0404 (10)	−0.0014 (9)	0.0201 (9)	−0.0033 (8)
C19	0.0617 (13)	0.0432 (11)	0.0459 (10)	0.0005 (9)	0.0154 (9)	−0.0083 (9)
C20	0.0526 (11)	0.0420 (11)	0.0436 (10)	0.0004 (9)	0.0113 (9)	0.0017 (8)
C21	0.0712 (14)	0.0447 (12)	0.0538 (12)	−0.0011 (10)	0.0105 (11)	0.0070 (10)
N1	0.0576 (10)	0.0412 (9)	0.0430 (9)	−0.0053 (7)	0.0254 (8)	−0.0027 (7)
O1	0.0763 (10)	0.0586 (9)	0.0431 (7)	0.0152 (8)	0.0264 (7)	−0.0011 (6)
O2	0.0617 (10)	0.0802 (11)	0.0531 (9)	−0.0194 (8)	0.0167 (7)	0.0158 (7)
O3	0.0902 (12)	0.0585 (10)	0.0688 (10)	−0.0028 (8)	0.0300 (9)	0.0201 (8)
S1	0.0575 (3)	0.0437 (3)	0.0457 (3)	−0.0001 (2)	0.0254 (2)	0.0024 (2)

Geometric parameters (Å, º) top

C1—C2	1.488 (3)	C10—H10B	0.9700
C1—H1A	0.9600	C11—O2	1.364 (2)
C1—H1B	0.9600	C11—C14	1.378 (3)
C1—H1C	0.9600	C11—C12	1.383 (3)
C2—O1	1.437 (2)	C12—C13	1.381 (2)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C16	1.378 (2)
C3—O1	1.367 (2)	C13—H13	0.9300
C3—C6	1.384 (2)	C14—C15	1.378 (3)
C3—C4	1.393 (3)	C14—H14	0.9300
C4—C5	1.377 (2)	C15—C16	1.376 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C8	1.390 (2)	C16—N1	1.437 (2)
C5—H5	0.9300	C17—N1	1.364 (3)
C6—C7	1.381 (2)	C17—C18	1.378 (2)
C6—H6	0.9300	C17—S1	1.7321 (17)
C7—C8	1.375 (3)	C18—C19	1.390 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—N1	1.443 (2)	C19—C20	1.368 (2)
C9—C10	1.510 (3)	C19—H19	0.9300
C9—H9A	0.9600	C20—C21	1.427 (3)
C9—H9B	0.9600	C20—S1	1.7330 (19)
C9—H9C	0.9600	C21—O3	1.221 (2)
C10—O2	1.423 (2)	C21—H21	0.9300
C10—H10A	0.9700

C2—C1—H1A	109.5	H10A—C10—H10B	108.5
C2—C1—H1B	109.5	O2—C11—C14	115.37 (17)
H1A—C1—H1B	109.5	O2—C11—C12	125.80 (17)
C2—C1—H1C	109.5	C14—C11—C12	118.83 (17)
H1A—C1—H1C	109.5	C13—C12—C11	120.11 (17)
H1B—C1—H1C	109.5	C13—C12—H12	119.9
O1—C2—C1	107.78 (18)	C11—C12—H12	119.9
O1—C2—H2A	110.2	C16—C13—C12	120.64 (17)
C1—C2—H2A	110.2	C16—C13—H13	119.7
O1—C2—H2B	110.2	C12—C13—H13	119.7
C1—C2—H2B	110.2	C15—C14—C11	121.07 (19)
H2A—C2—H2B	108.5	C15—C14—H14	119.5
O1—C3—C6	124.24 (17)	C11—C14—H14	119.5
O1—C3—C4	116.30 (16)	C16—C15—C14	120.04 (18)
C6—C3—C4	119.45 (16)	C16—C15—H15	120.0
C5—C4—C3	120.57 (17)	C14—C15—H15	120.0
C5—C4—H4	119.7	C15—C16—C13	119.28 (17)
C3—C4—H4	119.7	C15—C16—N1	118.78 (16)
C4—C5—C8	119.62 (18)	C13—C16—N1	121.92 (16)
C4—C5—H5	120.2	N1—C17—C18	128.87 (16)
C8—C5—H5	120.2	N1—C17—S1	119.71 (13)
C7—C6—C3	119.69 (17)	C18—C17—S1	111.41 (15)
C7—C6—H6	120.2	C17—C18—C19	112.33 (17)
C3—C6—H6	120.2	C17—C18—H18	123.8
C8—C7—C6	120.89 (16)	C19—C18—H18	123.8
C8—C7—H7	119.6	C20—C19—C18	114.29 (17)
C6—C7—H7	119.6	C20—C19—H19	122.9
C7—C8—C5	119.72 (16)	C18—C19—H19	122.9
C7—C8—N1	119.36 (15)	C19—C20—C21	130.17 (19)
C5—C8—N1	120.92 (17)	C19—C20—S1	110.73 (14)
C10—C9—H9A	109.5	C21—C20—S1	119.08 (15)
C10—C9—H9B	109.5	O3—C21—C20	125.0 (2)
H9A—C9—H9B	109.5	O3—C21—H21	117.5
C10—C9—H9C	109.5	C20—C21—H21	117.5
H9A—C9—H9C	109.5	C17—N1—C16	121.39 (14)
H9B—C9—H9C	109.5	C17—N1—C8	120.02 (14)
O2—C10—C9	107.39 (18)	C16—N1—C8	117.85 (15)
O2—C10—H10A	110.2	C3—O1—C2	117.19 (15)
C9—C10—H10A	110.2	C11—O2—C10	117.79 (15)
O2—C10—H10B	110.2	C17—S1—C20	91.23 (9)
C9—C10—H10B	110.2

O1—C3—C4—C5	−179.17 (18)	C19—C20—C21—O3	176.6 (2)
C6—C3—C4—C5	0.8 (3)	S1—C20—C21—O3	−1.2 (3)
C3—C4—C5—C8	1.0 (3)	C18—C17—N1—C16	−13.9 (3)
O1—C3—C6—C7	178.88 (17)	S1—C17—N1—C16	167.25 (13)
C4—C3—C6—C7	−1.1 (3)	C18—C17—N1—C8	176.16 (18)
C3—C6—C7—C8	−0.4 (3)	S1—C17—N1—C8	−2.7 (2)
C6—C7—C8—C5	2.2 (3)	C15—C16—N1—C17	130.0 (2)
C6—C7—C8—N1	−177.18 (16)	C13—C16—N1—C17	−51.4 (3)
C4—C5—C8—C7	−2.5 (3)	C15—C16—N1—C8	−59.9 (2)
C4—C5—C8—N1	176.91 (17)	C13—C16—N1—C8	118.7 (2)
O2—C11—C12—C13	−179.35 (19)	C7—C8—N1—C17	113.3 (2)
C14—C11—C12—C13	0.1 (3)	C5—C8—N1—C17	−66.1 (2)
C11—C12—C13—C16	1.5 (3)	C7—C8—N1—C16	−57.0 (2)
O2—C11—C14—C15	178.1 (2)	C5—C8—N1—C16	123.60 (19)
C12—C11—C14—C15	−1.4 (4)	C6—C3—O1—C2	−4.8 (3)
C11—C14—C15—C16	1.0 (4)	C4—C3—O1—C2	175.18 (17)
C14—C15—C16—C13	0.7 (3)	C1—C2—O1—C3	−179.38 (18)
C14—C15—C16—N1	179.3 (2)	C14—C11—O2—C10	−177.71 (19)
C12—C13—C16—C15	−1.9 (3)	C12—C11—O2—C10	1.8 (3)
C12—C13—C16—N1	179.50 (18)	C9—C10—O2—C11	179.51 (18)
N1—C17—C18—C19	−178.39 (18)	N1—C17—S1—C20	178.13 (15)
S1—C17—C18—C19	0.5 (2)	C18—C17—S1—C20	−0.88 (14)
C17—C18—C19—C20	0.3 (3)	C19—C20—S1—C17	1.03 (15)
C18—C19—C20—C21	−178.9 (2)	C21—C20—S1—C17	179.24 (16)
C18—C19—C20—S1	−1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.97	2.55	3.470 (3)	159

Symmetry code: (i) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.97	2.55	3.470 (3)	159

Symmetry code: (i) x, y−1, z.

Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant Nos. 21271004 and 51372003) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

References

Bedworth, P. V., Cai, Y., Jen, A. & Marder, S. R. (1996). J. Org. Chem. 61, o2242–o2246. CrossRef Web of Science Google Scholar
Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hansel, H., Zettl, H., Krausch, G., Kisselev, R., Thelakkat, M. & Schmidt, H. W. (2003). Adv. Mater. 15, 2056–2060. Google Scholar
Justin Thomas, K. R., Hsu, Y. C., Lin, J. T., Lee, K. M., Ho, K. C., Lai, C. H., Cheng, Y. M. & Chou, P. T. (2008). Chem. Mater. 20, 1830–1840. Web of Science CrossRef Google Scholar
Li, R., Li, D.-D. & Wu, J.-Y. (2013). Acta Cryst. E69, o1405. CSD CrossRef IUCr Journals Google Scholar
Mazzeo, M., Vitale, V., Della Sala, F., Pisignano, D., Anni, M., Barbarella, G., Favaretto, L., Zanelli, A., Cingolani, R. & Gigli, G. (2003). Adv. Mater. 15, 2060–2063. Web of Science CrossRef CAS Google Scholar
Raposo, M. M. M., Fonseca, A. M. C., Castro, M. C. R., Belsley, M., Cardoso, M. F. S., Carvalho, L. M. & Coelho, P. J. (2011). Dyes Pigm. 91, 62–73. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takekuma, S. I., Takahashi, K., Sakaguchi, A., Shibata, Y., Sasaki, M., Minematsu, T. & Takekuma, H. (2005). Tetrahedron, 61, 10349–10362. Web of Science CSD CrossRef CAS Google Scholar
Wurthner, F., Yao, S., Debaerdemaeker, T. & Wortmann, R. (2002). J. Am. Chem. Soc. 124, 9431–9447. Web of Science PubMed Google Scholar
Zhan, X., Tan, Z.-A., Domercq, B., An, Z., Zhang, X., Barlow, S., Li, Y.-F., Zhu, D.-B., Kippelen, B. & Marder, S. R. (2007). J. Am. Chem. Soc. 129, 7246–7247. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 70| Part 9| September 2014| Pages o1075-o1076

doi:10.1107/S1600536814018984

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 5-[bis­­(4-eth­­oxy­phenyl)amino]­thio­phene-2-carbaldehyde

1. Related literature

2. Experimental

2.1. Crystal data

2.1.2. Data collection

2.1.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 5-[bis(4-ethoxyphenyl)amino]thiophene-2-carbaldehyde