Crystal structure of 9-butyl-3-(9-butyl-9H-carbazol-3-yl)-9H-carbazole.

In the title carbazole derivative, C32H32N2, the mol-ecule resides on a crystallographic twofold axis, which runs through the central C-C bond. The carbazole ring system is almost planar, with a maximum deviation of 0.041 (1) Å for one of the ring-junction C atoms. The crystal packing is stabilized by C-H⋯π inter-actions only, which form a C(7) chain-like arrangement along [110] in the unit cell.

Related literature

For general background to carbazole derivatives and their applications, see: Giraud et al. (2014 ▶); Bandgar et al. (2012 ▶); Gu et al. (2014 ▶); Wang et al. (2011 ▶); Thiratmatrakul et al. (2014 ▶); Shi et al. (2012 ▶); Tavasli et al. (2012 ▶); Kim et al. (2011 ▶); Zhuang et al. (2012 ▶). For the preparation of the title compound, see: Ramalingan et al. (2010 ▶).

Experimental

Crystal data

C32H32N2

M = 444.59

Monoclinic,

a = 5.6184 (4) Å

b = 11.0946 (7) Å

c = 19.4673 (13) Å

β = 95.982 (1)°

V = 1206.86 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 292 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

13872 measured reflections

2928 independent reflections

2319 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.159

S = 1.12

2928 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814025367/zq2229sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025367/zq2229Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814025367/zq2229Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814025367/zq2229fig1.tif

The mol­ecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814025367/zq2229fig2.tif

Mol­ecular packing of the title compound, viewed along the a axis; C—H⋯π inter­actions are shown as dashed lines·For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted for clarity.

CCDC reference: 1034987

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

C32H32N2	F(000) = 476
Mr = 444.59	Dx = 1.223 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6184 (4) Å	Cell parameters from 9858 reflections
b = 11.0946 (7) Å	θ = 2.4–27.2°
c = 19.4673 (13) Å	µ = 0.07 mm−1
β = 95.982 (1)°	T = 292 K
V = 1206.86 (14) Å3	Block, colourless
Z = 2	0.21 × 0.19 × 0.17 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.026
Radiation source: fine-focus sealed tube	θmax = 28.3°, θmin = 2.1°
ω scans	h = −7→7
13872 measured reflections	k = −14→14
2928 independent reflections	l = −25→25
2319 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0782P)2 + 0.1445P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2928 reflections	Δρmax = 0.24 e Å−3
155 parameters	Δρmin = −0.19 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.

	x	y	z	Uiso*/Ueq
N1	0.3407 (2)	0.68730 (12)	0.15991 (7)	0.0515 (4)
C1	0.2740 (3)	0.77442 (13)	0.11101 (8)	0.0453 (4)
C2	0.3743 (3)	0.80464 (14)	0.05125 (9)	0.0520 (4)
H2	0.5112	0.7659	0.0395	0.062*
C3	0.2664 (3)	0.89298 (14)	0.00987 (8)	0.0498 (4)
H3	0.3343	0.9134	−0.0301	0.060*
C4	0.0581 (3)	0.95478 (12)	0.02450 (7)	0.0432 (3)
C5	−0.0317 (3)	0.92638 (13)	0.08650 (8)	0.0464 (4)
H5	−0.1644	0.9677	0.0991	0.056*
C6	0.0733 (3)	0.83737 (14)	0.12995 (7)	0.0445 (4)
C7	0.0185 (3)	0.78577 (14)	0.19467 (8)	0.0487 (4)
C8	−0.1572 (3)	0.80724 (17)	0.23854 (9)	0.0601 (5)
H8	−0.2688	0.8685	0.2289	0.072*
C9	−0.1633 (4)	0.7361 (2)	0.29660 (9)	0.0711 (5)
H9	−0.2801	0.7496	0.3263	0.085*
C10	0.0034 (4)	0.64469 (19)	0.31106 (10)	0.0718 (6)
H10	−0.0045	0.5980	0.3504	0.086*
C11	0.1792 (4)	0.62115 (17)	0.26904 (9)	0.0627 (5)
H11	0.2900	0.5598	0.2793	0.075*
C12	0.1855 (3)	0.69250 (14)	0.21042 (8)	0.0502 (4)
C13	0.5130 (3)	0.59184 (15)	0.15104 (9)	0.0572 (4)
H13A	0.5533	0.5518	0.1950	0.069*
H13B	0.6584	0.6275	0.1372	0.069*
C14	0.4206 (3)	0.49911 (16)	0.09770 (9)	0.0580 (4)
H14A	0.3929	0.5386	0.0531	0.070*
H14B	0.5439	0.4388	0.0944	0.070*
C15	0.1935 (3)	0.43619 (18)	0.11230 (10)	0.0661 (5)
H15A	0.0679	0.4957	0.1143	0.079*
H15B	0.2191	0.3973	0.1571	0.079*
C16	0.1125 (4)	0.3428 (2)	0.05817 (12)	0.0911 (7)
H16A	0.0976	0.3797	0.0133	0.137*
H16B	−0.0396	0.3107	0.0674	0.137*
H16C	0.2281	0.2789	0.0595	0.137*

	U11	U22	U33	U12	U13	U23
N1	0.0529 (7)	0.0499 (8)	0.0513 (8)	0.0010 (6)	0.0039 (6)	0.0007 (6)
C1	0.0430 (7)	0.0437 (8)	0.0487 (8)	−0.0055 (6)	0.0015 (6)	−0.0043 (6)
C2	0.0426 (8)	0.0532 (9)	0.0618 (10)	0.0013 (7)	0.0127 (7)	0.0005 (7)
C3	0.0476 (8)	0.0525 (9)	0.0511 (9)	−0.0050 (7)	0.0130 (7)	0.0015 (7)
C4	0.0439 (7)	0.0388 (7)	0.0468 (8)	−0.0065 (6)	0.0050 (6)	−0.0071 (6)
C5	0.0473 (8)	0.0457 (8)	0.0467 (8)	0.0007 (6)	0.0077 (6)	−0.0086 (6)
C6	0.0469 (8)	0.0437 (8)	0.0428 (8)	−0.0066 (6)	0.0049 (6)	−0.0089 (6)
C7	0.0543 (9)	0.0495 (8)	0.0420 (8)	−0.0086 (7)	0.0035 (6)	−0.0092 (7)
C8	0.0673 (11)	0.0648 (11)	0.0494 (9)	−0.0063 (8)	0.0124 (8)	−0.0130 (8)
C9	0.0836 (13)	0.0846 (14)	0.0484 (10)	−0.0165 (11)	0.0218 (9)	−0.0116 (9)
C10	0.0935 (14)	0.0744 (13)	0.0483 (10)	−0.0190 (11)	0.0109 (10)	0.0034 (9)
C11	0.0759 (12)	0.0602 (10)	0.0511 (10)	−0.0085 (9)	0.0019 (8)	0.0033 (8)
C12	0.0558 (9)	0.0498 (9)	0.0441 (8)	−0.0093 (7)	0.0015 (7)	−0.0056 (6)
C13	0.0491 (9)	0.0559 (10)	0.0651 (10)	0.0031 (7)	−0.0010 (7)	0.0033 (8)
C14	0.0574 (10)	0.0579 (10)	0.0594 (10)	0.0074 (8)	0.0090 (8)	0.0012 (8)
C15	0.0651 (11)	0.0693 (11)	0.0643 (11)	−0.0039 (9)	0.0089 (9)	−0.0126 (9)
C16	0.0988 (17)	0.0948 (16)	0.0795 (14)	−0.0229 (13)	0.0083 (12)	−0.0273 (13)

N1—C1	1.381 (2)	C9—C10	1.389 (3)
N1—C12	1.382 (2)	C9—H9	0.9300
N1—C13	1.457 (2)	C10—C11	1.372 (3)
C1—C2	1.385 (2)	C10—H10	0.9300
C1—C6	1.408 (2)	C11—C12	1.392 (2)
C2—C3	1.369 (2)	C11—H11	0.9300
C2—H2	0.9300	C13—C14	1.515 (2)
C3—C4	1.411 (2)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.392 (2)	C14—C15	1.507 (3)
C4—C4i	1.488 (3)	C14—H14A	0.9700
C5—C6	1.391 (2)	C14—H14B	0.9700
C5—H5	0.9300	C15—C16	1.514 (3)
C6—C7	1.446 (2)	C15—H15A	0.9700
C7—C8	1.392 (2)	C15—H15B	0.9700
C7—C12	1.409 (2)	C16—H16A	0.9600
C8—C9	1.382 (3)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C1—N1—C12	108.37 (13)	C9—C10—H10	119.0
C1—N1—C13	124.27 (14)	C10—C11—C12	117.53 (19)
C12—N1—C13	126.23 (14)	C10—C11—H11	121.2
N1—C1—C2	130.04 (14)	C12—C11—H11	121.2
N1—C1—C6	109.51 (13)	N1—C12—C11	129.16 (16)
C2—C1—C6	120.44 (14)	N1—C12—C7	109.34 (14)
C3—C2—C1	118.26 (14)	C11—C12—C7	121.50 (16)
C3—C2—H2	120.9	N1—C13—C14	112.98 (14)
C1—C2—H2	120.9	N1—C13—H13A	109.0
C2—C3—C4	123.69 (15)	C14—C13—H13A	109.0
C2—C3—H3	118.2	N1—C13—H13B	109.0
C4—C3—H3	118.2	C14—C13—H13B	109.0
C5—C4—C3	116.63 (14)	H13A—C13—H13B	107.8
C5—C4—C4i	122.27 (17)	C15—C14—C13	114.95 (15)
C3—C4—C4i	121.10 (17)	C15—C14—H14A	108.5
C6—C5—C4	121.26 (14)	C13—C14—H14A	108.5
C6—C5—H5	119.4	C15—C14—H14B	108.5
C4—C5—H5	119.4	C13—C14—H14B	108.5
C5—C6—C1	119.57 (13)	H14A—C14—H14B	107.5
C5—C6—C7	134.08 (14)	C14—C15—C16	112.63 (16)
C1—C6—C7	106.31 (14)	C14—C15—H15A	109.1
C8—C7—C12	119.42 (15)	C16—C15—H15A	109.1
C8—C7—C6	134.10 (16)	C14—C15—H15B	109.1
C12—C7—C6	106.44 (14)	C16—C15—H15B	109.1
C9—C8—C7	118.93 (18)	H15A—C15—H15B	107.8
C9—C8—H8	120.5	C15—C16—H16A	109.5
C7—C8—H8	120.5	C15—C16—H16B	109.5
C8—C9—C10	120.59 (18)	H16A—C16—H16B	109.5
C8—C9—H9	119.7	C15—C16—H16C	109.5
C10—C9—H9	119.7	H16A—C16—H16C	109.5
C11—C10—C9	122.02 (18)	H16B—C16—H16C	109.5
C11—C10—H10	119.0
C12—N1—C1—C2	179.62 (16)	C1—C6—C7—C12	−1.41 (16)
C13—N1—C1—C2	−11.9 (2)	C12—C7—C8—C9	0.0 (2)
C12—N1—C1—C6	0.15 (16)	C6—C7—C8—C9	177.40 (16)
C13—N1—C1—C6	168.63 (13)	C7—C8—C9—C10	0.1 (3)
N1—C1—C2—C3	177.59 (14)	C8—C9—C10—C11	0.0 (3)
C6—C1—C2—C3	−3.0 (2)	C9—C10—C11—C12	−0.1 (3)
C1—C2—C3—C4	−0.2 (2)	C1—N1—C12—C11	178.61 (16)
C2—C3—C4—C5	3.2 (2)	C13—N1—C12—C11	10.4 (3)
C2—C3—C4—C4i	−176.60 (16)	C1—N1—C12—C7	−1.07 (17)
C3—C4—C5—C6	−2.9 (2)	C13—N1—C12—C7	−169.27 (14)
C4i—C4—C5—C6	176.86 (15)	C10—C11—C12—N1	−179.47 (16)
C4—C5—C6—C1	−0.1 (2)	C10—C11—C12—C7	0.2 (2)
C4—C5—C6—C7	−177.52 (15)	C8—C7—C12—N1	179.62 (14)
N1—C1—C6—C5	−177.26 (13)	C6—C7—C12—N1	1.54 (17)
C2—C1—C6—C5	3.2 (2)	C8—C7—C12—C11	−0.1 (2)
N1—C1—C6—C7	0.79 (16)	C6—C7—C12—C11	−178.17 (14)
C2—C1—C6—C7	−178.73 (14)	C1—N1—C13—C14	−69.5 (2)
C5—C6—C7—C8	−1.4 (3)	C12—N1—C13—C14	96.88 (19)
C1—C6—C7—C8	−179.08 (17)	N1—C13—C14—C15	−58.5 (2)
C5—C6—C7—C12	176.24 (15)	C13—C14—C15—C16	−178.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Cgii	0.97	2.98	3.838 (2)	148

Table 1

Hydrogen-bond geometry (, )

Cg is the centroid of the C7C12 ring.

DHA	DH	HA	D A	DHA
C15H15B Cg i	0.97	2.98	3.838(2)	148

Symmetry code: (i) .