(E)-3-(9-Hexyl-9H-carbazol-3-yl)acrylic acid

Sun, W.; Liu, W.-M.; Li, S.-L.

doi:10.1107/S1600536814016237

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o884

doi:10.1107/S1600536814016237

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(E)-3-(9-Hexyl-9H-carbazol-3-yl)acrylic acid

Wan Sun,^a,^b Wen-Mo Liu ^a,^b and Sheng-Li Li ^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: lsl1968@ahu.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 5 June 2014; accepted 12 July 2014; online 31 July 2014)

In the title compound, C₂₁H₂₃NO₂, the hexyl group adopts an extended conformation, the six C atoms are nearly coplanar [maximum deviation = 0.082 (3) Å] and their mean plane is approximately perpendicular to the carbazole ring system, with a dihedral angle of 78.91 (15)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming inversion dimers; π–π stacking between carbazole ring systems of adjacent dimers further links the dimers into supramolecular chains propagating along the b-axis direction [centroid-to-centroid distances = 3.868 (2) and 3.929 (2) Å].

Keywords: crystal structure.

CCDC reference: 992361

Related literature

For structures of related carbazole derivatives, see: Saeed et al. (2010 ). For applications of carbazole derivatives, see: Adhikari et al. (2009 ); Daicho et al. (2013 ); Tao et al. (2010 ); Zheng et al. (2012 ); Dvornikov et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₃NO₂
M_r = 321.40
Monoclinic, P 2₁ /n
a = 10.594 (5) Å
b = 5.109 (2) Å
c = 33.152 (15) Å
β = 94.922 (6)°
V = 1787.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
11882 measured reflections
3115 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.192
S = 1.07
3115 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.85	2.650 (3)	166
Symmetry code: (i) -x+2, -y-2, -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: 992361

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814016237/xu5796sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016237/xu5796Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016237/xu5796Isup3.cml

checkCIF report

Comment top

Recently, carbazole derivatives have attracted attention as their superphotoelectric effect (Tao et al., 2010) and electron transporting capabilities (Zheng et al., 2012). So they have been widely used in biochemistry optical switching (Adhikari et al., 2009), 3-D microfabrication (Daicho et al., 2013) and optical data storage (Dvornikov et al., 2009). In the present paper, the title carbazole derivative (Fig.1) is synthesized.

In the molecule, the carbazole and carboxylic acid are coplanar, while the hexyl group is nearly perpendicular to the plan of carbazole ring [dihedral angle = 78.91 (15)°]. The molecule connect with each other by intermolecular hydrogen-bonding O1—H1···O2.

Related literature top

For structures of related carbazole derivatives, see: Saeed et al. (2010). For applications of carbazole derivatives, see: Adhikari et al. (2009); Daicho et al. (2013); Tao et al. (2010); Zheng et al. (2012); Dvornikov et al. (2009).

Experimental top

Carbazole single aldehyde (1.6 g, 5 mmol) and malonic acid (1.04 g, 10 mmol) was dissolved in pyridine with addition of 0.1 ml piperidine. The mixture was refluxed for 3 h, traced by TLC then column chromatography (silica, petroleum ether: ethyl acetate (V/V) = 5: 1) and finally 1.2 g white solid were acquired. Yield: 37%. 0.1 g LCOOH was dissolved in 30 ml me thanol, filtered to 50 ml volumetric flask, naturally evaporated for a week, and then colorless single crystals were obtained. ¹H NMR (400 MHz, CD₃COCD₃) 0.84 (t, 3H), 1.33 (m, 6H), 1.89 (m, 2H), 4.46 (t, 2H), 6.59 (d, 1H), 7.26 (t, 1H), 7.50 (t, 1H), 7.62 (t, 2H), 7.82 (d, 1H), 7.87 (d, 1H), 8.23 (t, 1H), 8.51 (s, 1H), 10.53 (s, 1H).

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 showing 30% probability displacement ellipsoids.

(E)-3-(9-Hexyl-9H-carbazol-3-yl)acrylic acid top

Crystal data top

C₂₁H₂₃NO₂	F(000) = 688
M_r = 321.40	D_x = 1.194 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 425 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.594 (5) Å	Cell parameters from 2128 reflections
b = 5.109 (2) Å	θ = 4.2–20.6°
c = 33.152 (15) Å	µ = 0.08 mm⁻¹
β = 94.922 (6)°	T = 298 K
V = 1787.5 (14) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2291 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 1.2°
phi and ω scans	h = −12→12
11882 measured reflections	k = −6→5
3115 independent reflections	l = −39→38

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1029P)² + 0.5377P] where P = (F_o² + 2F_c²)/3
3115 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₂₃NO₂	V = 1787.5 (14) Å³
M_r = 321.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.594 (5) Å	µ = 0.08 mm⁻¹
b = 5.109 (2) Å	T = 298 K
c = 33.152 (15) Å	0.30 × 0.20 × 0.20 mm
β = 94.922 (6)°

Data collection top

Bruker SMART APEX CCD diffractometer	2291 reflections with I > 2σ(I)
11882 measured reflections	R_int = 0.027
3115 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.07	Δρ_max = 0.47 e Å⁻³
3115 reflections	Δρ_min = −0.26 e Å⁻³
219 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	0.7326 (2)	0.3637 (5)	0.18010 (7)	0.0663 (7)
H1A	0.8098	0.2762	0.1834	0.080*
C2	0.7043 (3)	0.5596 (5)	0.20667 (8)	0.0774 (8)
H2	0.7634	0.6047	0.2279	0.093*
C3	0.5892 (3)	0.6895 (5)	0.20204 (8)	0.0758 (8)
H3	0.5727	0.8210	0.2203	0.091*
C4	0.4993 (3)	0.6291 (5)	0.17135 (8)	0.0698 (7)
H4	0.4220	0.7164	0.1686	0.084*
C5	0.5273 (2)	0.4319 (4)	0.14423 (7)	0.0570 (6)
C6	0.6441 (2)	0.2999 (4)	0.14841 (6)	0.0535 (6)
C7	0.64129 (19)	0.1119 (4)	0.11537 (6)	0.0500 (6)
C8	0.5225 (2)	0.1420 (4)	0.09295 (6)	0.0526 (6)
C9	0.4886 (2)	−0.0077 (5)	0.05871 (6)	0.0598 (6)
H9	0.4102	0.0127	0.0442	0.072*
C10	0.5756 (2)	−0.1879 (5)	0.04707 (6)	0.0587 (6)
H10	0.5545	−0.2896	0.0242	0.070*
C11	0.6947 (2)	−0.2234 (4)	0.06846 (6)	0.0529 (6)
C12	0.7261 (2)	−0.0701 (4)	0.10286 (6)	0.0532 (6)
H12	0.8045	−0.0909	0.1174	0.064*
C13	0.7861 (2)	−0.4127 (4)	0.05570 (6)	0.0568 (6)
H13	0.8624	−0.4229	0.0718	0.068*
C14	0.7743 (2)	−0.5720 (5)	0.02407 (7)	0.0609 (6)
H14	0.6993	−0.5668	0.0073	0.073*
C15	0.8722 (2)	−0.7543 (5)	0.01418 (7)	0.0605 (6)
C16	0.3276 (2)	0.4227 (5)	0.09634 (8)	0.0730 (8)
H16A	0.3211	0.4295	0.0670	0.088*
H16B	0.3152	0.5989	0.1062	0.088*
C17	0.2239 (2)	0.2500 (7)	0.10958 (9)	0.0903 (10)
H17A	0.1432	0.3267	0.0998	0.108*
H17B	0.2298	0.0817	0.0963	0.108*
C18	0.2226 (3)	0.2040 (7)	0.15327 (9)	0.0911 (9)
H18A	0.2115	0.3705	0.1666	0.109*
H18B	0.3042	0.1341	0.1635	0.109*
C19	0.1198 (3)	0.0179 (7)	0.16456 (13)	0.1166 (13)
H19A	0.1239	−0.1415	0.1488	0.140*
H19B	0.0377	0.0976	0.1576	0.140*
C20	0.1322 (5)	−0.0535 (9)	0.21078 (15)	0.1420 (17)
H20A	0.2163	−0.1242	0.2177	0.170*
H20B	0.1252	0.1065	0.2262	0.170*
C21	0.0420 (5)	−0.2353 (11)	0.22313 (17)	0.182 (2)
H21A	0.0430	−0.3896	0.2066	0.273*
H21B	−0.0409	−0.1579	0.2201	0.273*
H21C	0.0628	−0.2813	0.2510	0.273*
N1	0.45361 (17)	0.3355 (4)	0.11062 (5)	0.0585 (5)
O1	0.84699 (17)	−0.8937 (4)	−0.01813 (5)	0.0839 (6)
H1	0.9106	−0.9745	−0.0233	0.126*
O2	0.97385 (16)	−0.7732 (4)	0.03562 (5)	0.0849 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0730 (16)	0.0645 (15)	0.0614 (14)	0.0008 (13)	0.0060 (12)	−0.0050 (12)
C2	0.095 (2)	0.0748 (19)	0.0621 (15)	−0.0061 (15)	0.0069 (13)	−0.0155 (13)
C3	0.099 (2)	0.0602 (16)	0.0706 (16)	0.0007 (15)	0.0238 (14)	−0.0148 (13)
C4	0.0798 (17)	0.0579 (15)	0.0750 (16)	0.0120 (13)	0.0253 (13)	−0.0025 (13)
C5	0.0688 (15)	0.0494 (13)	0.0548 (12)	0.0067 (11)	0.0171 (10)	0.0024 (10)
C6	0.0622 (13)	0.0493 (13)	0.0502 (12)	0.0028 (10)	0.0116 (10)	0.0018 (10)
C7	0.0546 (13)	0.0495 (13)	0.0470 (11)	0.0044 (10)	0.0108 (9)	0.0043 (9)
C8	0.0566 (13)	0.0546 (13)	0.0481 (11)	0.0076 (10)	0.0121 (9)	0.0044 (10)
C9	0.0546 (13)	0.0713 (15)	0.0532 (12)	0.0123 (12)	0.0036 (9)	0.0000 (11)
C10	0.0625 (14)	0.0648 (15)	0.0490 (12)	0.0049 (11)	0.0057 (10)	−0.0078 (10)
C11	0.0558 (13)	0.0536 (13)	0.0499 (12)	0.0084 (10)	0.0092 (9)	0.0006 (10)
C12	0.0539 (13)	0.0539 (14)	0.0519 (12)	0.0075 (10)	0.0040 (9)	0.0005 (10)
C13	0.0576 (13)	0.0588 (14)	0.0541 (12)	0.0078 (11)	0.0053 (10)	−0.0049 (11)
C14	0.0583 (14)	0.0676 (16)	0.0566 (13)	0.0130 (11)	0.0037 (10)	−0.0060 (11)
C15	0.0600 (14)	0.0662 (15)	0.0552 (13)	0.0116 (11)	0.0038 (10)	−0.0103 (11)
C16	0.0710 (17)	0.0803 (19)	0.0681 (15)	0.0281 (14)	0.0088 (12)	0.0062 (13)
C17	0.0615 (16)	0.123 (3)	0.0839 (19)	0.0204 (17)	−0.0066 (14)	−0.0058 (17)
C18	0.0790 (19)	0.089 (2)	0.107 (2)	0.0104 (16)	0.0196 (16)	−0.0084 (18)
C19	0.095 (2)	0.101 (3)	0.160 (3)	−0.012 (2)	0.052 (2)	−0.024 (2)
C20	0.151 (4)	0.126 (3)	0.158 (4)	−0.042 (3)	0.066 (3)	−0.020 (3)
C21	0.189 (5)	0.129 (4)	0.245 (6)	−0.028 (3)	0.117 (5)	−0.021 (4)
N1	0.0601 (11)	0.0592 (12)	0.0572 (11)	0.0153 (9)	0.0108 (9)	0.0002 (9)
O1	0.0744 (12)	0.1000 (15)	0.0750 (11)	0.0311 (11)	−0.0068 (9)	−0.0370 (10)
O2	0.0699 (12)	0.1028 (15)	0.0789 (12)	0.0305 (10)	−0.0121 (9)	−0.0354 (11)

Geometric parameters (Å, º) top

C1—C2	1.383 (4)	C14—C15	1.452 (3)
C1—C6	1.386 (3)	C14—H14	0.9300
C1—H1A	0.9300	C15—O2	1.242 (3)
C2—C3	1.385 (4)	C15—O1	1.295 (3)
C2—H2	0.9300	C16—N1	1.448 (3)
C3—C4	1.368 (3)	C16—C17	1.504 (4)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.399 (3)	C16—H16B	0.9700
C4—H4	0.9300	C17—C18	1.469 (4)
C5—N1	1.394 (3)	C17—H17A	0.9700
C5—C6	1.406 (3)	C17—H17B	0.9700
C6—C7	1.455 (3)	C18—C19	1.517 (5)
C7—C12	1.381 (3)	C18—H18A	0.9700
C7—C8	1.414 (3)	C18—H18B	0.9700
C8—N1	1.387 (3)	C19—C20	1.570 (6)
C8—C9	1.390 (3)	C19—H19A	0.9700
C9—C10	1.380 (3)	C19—H19B	0.9700
C9—H9	0.9300	C20—C21	1.418 (6)
C10—C11	1.405 (3)	C20—H20A	0.9700
C10—H10	0.9300	C20—H20B	0.9700
C11—C12	1.400 (3)	C21—H21A	0.9600
C11—C13	1.457 (3)	C21—H21B	0.9600
C12—H12	0.9300	C21—H21C	0.9600
C13—C14	1.325 (3)	O1—H1	0.8200
C13—H13	0.9300

C2—C1—C6	118.9 (2)	O2—C15—C14	121.4 (2)
C2—C1—H1A	120.5	O1—C15—C14	116.04 (19)
C6—C1—H1A	120.5	N1—C16—C17	113.6 (2)
C1—C2—C3	120.9 (2)	N1—C16—H16A	108.8
C1—C2—H2	119.6	C17—C16—H16A	108.8
C3—C2—H2	119.6	N1—C16—H16B	108.8
C4—C3—C2	121.6 (2)	C17—C16—H16B	108.8
C4—C3—H3	119.2	H16A—C16—H16B	107.7
C2—C3—H3	119.2	C18—C17—C16	116.8 (2)
C3—C4—C5	117.9 (2)	C18—C17—H17A	108.1
C3—C4—H4	121.1	C16—C17—H17A	108.1
C5—C4—H4	121.1	C18—C17—H17B	108.1
N1—C5—C4	129.3 (2)	C16—C17—H17B	108.1
N1—C5—C6	109.70 (19)	H17A—C17—H17B	107.3
C4—C5—C6	121.0 (2)	C17—C18—C19	114.3 (3)
C1—C6—C5	119.7 (2)	C17—C18—H18A	108.7
C1—C6—C7	134.0 (2)	C19—C18—H18A	108.7
C5—C6—C7	106.33 (18)	C17—C18—H18B	108.7
C12—C7—C8	119.20 (19)	C19—C18—H18B	108.7
C12—C7—C6	134.30 (19)	H18A—C18—H18B	107.6
C8—C7—C6	106.49 (18)	C18—C19—C20	112.6 (3)
N1—C8—C9	128.9 (2)	C18—C19—H19A	109.1
N1—C8—C7	109.38 (19)	C20—C19—H19A	109.1
C9—C8—C7	121.7 (2)	C18—C19—H19B	109.1
C10—C9—C8	117.6 (2)	C20—C19—H19B	109.1
C10—C9—H9	121.2	H19A—C19—H19B	107.8
C8—C9—H9	121.2	C21—C20—C19	115.6 (4)
C9—C10—C11	122.5 (2)	C21—C20—H20A	108.4
C9—C10—H10	118.8	C19—C20—H20A	108.4
C11—C10—H10	118.8	C21—C20—H20B	108.4
C12—C11—C10	118.63 (19)	C19—C20—H20B	108.4
C12—C11—C13	119.4 (2)	H20A—C20—H20B	107.4
C10—C11—C13	122.0 (2)	C20—C21—H21A	109.5
C7—C12—C11	120.40 (19)	C20—C21—H21B	109.5
C7—C12—H12	119.8	H21A—C21—H21B	109.5
C11—C12—H12	119.8	C20—C21—H21C	109.5
C14—C13—C11	128.1 (2)	H21A—C21—H21C	109.5
C14—C13—H13	115.9	H21B—C21—H21C	109.5
C11—C13—H13	115.9	C8—N1—C5	108.09 (18)
C13—C14—C15	123.5 (2)	C8—N1—C16	125.8 (2)
C13—C14—H14	118.3	C5—N1—C16	126.14 (19)
C15—C14—H14	118.3	C15—O1—H1	109.5
O2—C15—O1	122.5 (2)

C1—C6—C7—C12	−0.7 (5)	N1—C5—C4—C3	−179.6 (2)
C5—C6—C7—C12	179.3 (2)	C6—C5—C4—C3	0.2 (4)
C1—C6—C7—C8	180.0 (3)	C15—C14—C13—C11	180.0 (2)
C5—C6—C7—C8	0.0 (2)	C12—C11—C13—C14	−179.3 (3)
C8—C7—C12—C11	0.0 (3)	C10—C11—C13—C14	0.2 (4)
C6—C7—C12—C11	−179.3 (2)	N1—C8—C9—C10	179.5 (2)
C10—C11—C12—C7	−0.1 (3)	C7—C8—C9—C10	−0.2 (4)
C13—C11—C12—C7	179.5 (2)	C8—C9—C10—C11	0.1 (4)
C5—N1—C8—C9	−179.5 (2)	C12—C11—C10—C9	0.1 (4)
C16—N1—C8—C9	−0.1 (4)	C13—C11—C10—C9	−179.5 (2)
C5—N1—C8—C7	0.3 (3)	C5—C4—C3—C2	−0.5 (4)
C16—N1—C8—C7	179.7 (2)	C13—C14—C15—O2	1.2 (4)
C12—C7—C8—N1	−179.60 (19)	C13—C14—C15—O1	−178.9 (3)
C6—C7—C8—N1	−0.2 (2)	C5—C6—C1—C2	−0.6 (4)
C12—C7—C8—C9	0.2 (3)	C7—C6—C1—C2	179.3 (3)
C6—C7—C8—C9	179.6 (2)	C6—C1—C2—C3	0.3 (4)
C8—N1—C5—C4	179.4 (2)	C4—C3—C2—C1	0.3 (5)
C16—N1—C5—C4	0.1 (4)	C16—C17—C18—C19	−177.5 (3)
C8—N1—C5—C6	−0.4 (3)	C17—C18—C19—C20	173.0 (3)
C16—N1—C5—C6	−179.7 (2)	C18—C19—C20—C21	−177.3 (4)
C1—C6—C5—N1	−179.8 (2)	C8—N1—C16—C17	81.9 (3)
C7—C6—C5—N1	0.2 (3)	C5—N1—C16—C17	−98.9 (3)
C1—C6—C5—C4	0.4 (4)	C18—C17—C16—N1	55.5 (4)
C7—C6—C5—C4	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.85	2.650 (3)	166

Symmetry code: (i) −x+2, −y−2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.85	2.650 (3)	166

Symmetry code: (i) −x+2, −y−2, −z.

Acknowledgements

This work was supported by Anhui Provincial Natural Science Foundation (grant No. 1308085MB24) and the Foundation of Educational Commission of Anhui Province, China (grant No. KJ2012A025).

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