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

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, mol-ecules 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 supra-molecular chains propagating along the b-axis direction [centroid-to-centroid distances = 3.868 (2) and 3.929 (2) Å].

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 = 321.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.192

S = 1.07

3115 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.26 e Å−3

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.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814016237/xu5796sup1.cif

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

Click here for additional data file.

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

CCDC reference: 992361

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H23NO2	F(000) = 688
Mr = 321.40	Dx = 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

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

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(Fo2) + (0.1029P)2 + 0.5377P] where P = (Fo2 + 2Fc2)/3
3115 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .