9-Ethyl-3,6-bis-(1H-imidazol-1-yl)-9H-carbazole.

In the crystal structure of the title compound, C(20)H(17)N(5), the two imidazole rings are twisted with respect to the carbazole plane, making dihedral angles of 55.8 (2) and 43.7 (2)°. The crystal structure is stabilized by weak C-H⋯N and C-H⋯π inter-actions.

Related literature

For general background, see: Mi et al. (2003 ▶).

Experimental

Crystal data

C20H17N5

M = 327.39

Triclinic,

a = 5.625 (2) Å

b = 8.826 (3) Å

c = 17.367 (6) Å

α = 92.698 (6)°

β = 96.011 (6)°

γ = 102.567 (6)°

V = 834.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.46 × 0.40 × 0.16 mm

Data collection

Bruker SMART APEX area-dectector diffractometer

Absorption correction: none

6040 measured reflections

2928 independent reflections

2611 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 1.06

2928 reflections

225 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013937/xu2412sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013937/xu2412Isup2.hkl

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

C20H17N5	Z = 2
Mr = 327.39	F000 = 344
Triclinic, P1	Dx = 1.302 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.625 (2) Å	Cell parameters from 2928 reflections
b = 8.826 (3) Å	θ = 1.2–25.0º
c = 17.367 (6) Å	µ = 0.08 mm−1
α = 92.698 (6)º	T = 293 (2) K
β = 96.011 (6)º	Prism, yellow
γ = 102.567 (6)º	0.46 × 0.40 × 0.16 mm
V = 834.8 (5) Å3

Bruker SMART APEX area-dectector diffractometer	2611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Monochromator: graphite	θmax = 25.0º
T = 293(2) K	θmin = 1.2º
φ and ω scans	h = −6→6
Absorption correction: none	k = −10→10
6040 measured reflections	l = −20→20
2928 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.1471P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.23 e Å−3
2928 reflections	Δρmin = −0.18 e Å−3
225 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (6)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
N2	0.49085 (19)	0.34017 (13)	0.10310 (6)	0.0435 (3)
N4	0.89546 (19)	0.72250 (13)	0.53896 (6)	0.0418 (3)
N5	0.6235 (2)	0.67394 (15)	0.62354 (7)	0.0553 (4)
N1	0.1184 (2)	0.19639 (15)	0.06703 (7)	0.0535 (3)
N3	1.2016 (2)	0.83688 (14)	0.24918 (7)	0.0484 (3)
C13	0.9898 (2)	0.75062 (15)	0.46637 (7)	0.0405 (3)
C5	0.8279 (3)	0.56084 (17)	0.09187 (8)	0.0485 (4)
H5	0.8010	0.5396	0.0383	0.058*
C9	0.7148 (2)	0.49327 (16)	0.21905 (7)	0.0432 (3)
H9	0.6179	0.4289	0.2500	0.052*
C12	1.1789 (2)	0.88178 (16)	0.46167 (8)	0.0459 (4)
H12	1.2463	0.9456	0.5062	0.055*
C7	1.0438 (2)	0.71535 (16)	0.20364 (8)	0.0438 (3)
C10	1.1590 (2)	0.82136 (16)	0.32594 (8)	0.0433 (3)
C11	1.2661 (2)	0.91729 (16)	0.39191 (8)	0.0476 (4)
H11	1.3933	1.0032	0.3890	0.057*
C8	0.8970 (2)	0.62019 (15)	0.25193 (7)	0.0416 (3)
C14	0.8859 (2)	0.65280 (15)	0.40123 (7)	0.0430 (3)
H14	0.7624	0.5652	0.4048	0.052*
C2	0.5129 (3)	0.22459 (17)	0.05004 (8)	0.0493 (4)
H2	0.6569	0.2093	0.0323	0.059*
C18	0.6561 (2)	0.68650 (16)	0.55011 (8)	0.0480 (4)
H18	0.5281	0.6722	0.5101	0.058*
C15	0.9703 (2)	0.68841 (15)	0.33029 (7)	0.0416 (3)
C1	0.2852 (3)	0.13828 (17)	0.02886 (8)	0.0515 (4)
H1	0.2460	0.0517	−0.0065	0.062*
C6	1.0107 (3)	0.68540 (17)	0.12343 (8)	0.0496 (4)
H6	1.1090	0.7476	0.0920	0.060*
C4	0.6822 (2)	0.46580 (16)	0.13922 (7)	0.0423 (3)
C16	1.0248 (3)	0.73427 (18)	0.61152 (8)	0.0503 (4)
H16	1.1944	0.7584	0.6235	0.060*
C19	1.3664 (3)	0.96821 (17)	0.22027 (9)	0.0535 (4)
H19A	1.3862	1.0591	0.2560	0.064*
H19B	1.2921	0.9914	0.1705	0.064*
C3	0.2492 (2)	0.31619 (17)	0.11053 (8)	0.0473 (4)
H3	0.1832	0.3784	0.1432	0.057*
C17	0.8562 (3)	0.70373 (19)	0.66187 (8)	0.0553 (4)
H17	0.8929	0.7030	0.7153	0.066*
C20	1.6114 (4)	0.9380 (3)	0.21097 (14)	0.0896 (6)
H20A	1.6872	0.9167	0.2602	0.134*
H20B	1.7120	1.0279	0.1923	0.134*
H20C	1.5936	0.8501	0.1744	0.134*

	U11	U22	U33	U12	U13	U23
N2	0.0408 (6)	0.0507 (7)	0.0374 (6)	0.0095 (5)	0.0013 (4)	−0.0020 (5)
N4	0.0403 (6)	0.0420 (6)	0.0403 (6)	0.0042 (5)	0.0040 (5)	−0.0012 (5)
N5	0.0514 (7)	0.0583 (8)	0.0555 (8)	0.0067 (6)	0.0152 (6)	0.0044 (6)
N1	0.0427 (6)	0.0611 (8)	0.0533 (7)	0.0076 (6)	0.0006 (5)	0.0001 (6)
N3	0.0488 (7)	0.0466 (7)	0.0447 (7)	−0.0022 (5)	0.0084 (5)	0.0065 (5)
C13	0.0394 (7)	0.0409 (7)	0.0390 (7)	0.0047 (5)	0.0032 (5)	0.0012 (5)
C5	0.0521 (8)	0.0574 (9)	0.0353 (7)	0.0114 (7)	0.0047 (6)	0.0030 (6)
C9	0.0449 (7)	0.0436 (7)	0.0383 (7)	0.0042 (6)	0.0046 (5)	0.0022 (5)
C12	0.0446 (7)	0.0426 (8)	0.0448 (8)	0.0011 (6)	0.0003 (6)	−0.0031 (6)
C7	0.0438 (7)	0.0449 (8)	0.0416 (7)	0.0066 (6)	0.0056 (5)	0.0053 (6)
C10	0.0418 (7)	0.0415 (7)	0.0441 (7)	0.0032 (6)	0.0052 (5)	0.0050 (6)
C11	0.0429 (7)	0.0419 (8)	0.0508 (8)	−0.0048 (6)	0.0032 (6)	0.0029 (6)
C8	0.0433 (7)	0.0413 (7)	0.0380 (7)	0.0044 (6)	0.0051 (5)	0.0040 (5)
C14	0.0431 (7)	0.0388 (7)	0.0423 (7)	−0.0003 (6)	0.0040 (6)	0.0016 (6)
C2	0.0449 (8)	0.0552 (9)	0.0468 (8)	0.0118 (6)	0.0047 (6)	−0.0083 (6)
C18	0.0394 (7)	0.0499 (8)	0.0505 (8)	0.0019 (6)	0.0051 (6)	−0.0001 (6)
C15	0.0424 (7)	0.0381 (7)	0.0407 (7)	0.0015 (6)	0.0034 (5)	0.0035 (5)
C1	0.0513 (8)	0.0511 (8)	0.0483 (8)	0.0082 (7)	−0.0004 (6)	−0.0066 (6)
C6	0.0501 (8)	0.0552 (9)	0.0423 (8)	0.0051 (7)	0.0107 (6)	0.0101 (6)
C4	0.0397 (7)	0.0461 (8)	0.0400 (7)	0.0090 (6)	0.0017 (5)	−0.0001 (6)
C16	0.0441 (7)	0.0650 (9)	0.0411 (8)	0.0121 (6)	0.0021 (6)	0.0021 (6)
C19	0.0554 (9)	0.0474 (8)	0.0565 (9)	0.0047 (7)	0.0124 (7)	0.0122 (7)
C3	0.0406 (7)	0.0574 (9)	0.0442 (7)	0.0124 (6)	0.0045 (6)	0.0001 (6)
C17	0.0595 (9)	0.0679 (10)	0.0404 (8)	0.0165 (7)	0.0082 (6)	0.0074 (7)
C20	0.0618 (11)	0.0954 (15)	0.1158 (18)	0.0141 (10)	0.0283 (11)	0.0259 (13)

N2—C3	1.3501 (17)	C7—C6	1.391 (2)
N2—C2	1.3769 (18)	C7—C8	1.4142 (18)
N2—C4	1.4336 (18)	C10—C11	1.3909 (19)
N4—C18	1.3512 (18)	C10—C15	1.4116 (19)
N4—C16	1.3750 (18)	C11—H11	0.9300
N4—C13	1.4299 (17)	C8—C15	1.4428 (19)
N5—C18	1.3135 (19)	C14—C15	1.3913 (19)
N5—C17	1.370 (2)	C14—H14	0.9300
N1—C3	1.3039 (18)	C2—C1	1.344 (2)
N1—C1	1.3748 (19)	C2—H2	0.9300
N3—C7	1.3867 (18)	C18—H18	0.9300
N3—C10	1.3867 (18)	C1—H1	0.9300
N3—C19	1.4629 (18)	C6—H6	0.9300
C13—C14	1.3844 (18)	C16—C17	1.350 (2)
C13—C12	1.403 (2)	C16—H16	0.9300
C5—C6	1.378 (2)	C19—C20	1.483 (2)
C5—C4	1.400 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C9—C4	1.3820 (19)	C3—H3	0.9300
C9—C8	1.3960 (18)	C17—H17	0.9300
C9—H9	0.9300	C20—H20A	0.9600
C12—C11	1.378 (2)	C20—H20B	0.9600
C12—H12	0.9300	C20—H20C	0.9600
C3—N2—C2	105.71 (11)	C1—C2—H2	126.8
C3—N2—C4	127.00 (11)	N2—C2—H2	126.8
C2—N2—C4	127.18 (11)	N5—C18—N4	112.78 (12)
C18—N4—C16	105.83 (11)	N5—C18—H18	123.6
C18—N4—C13	126.09 (11)	N4—C18—H18	123.6
C16—N4—C13	128.00 (11)	C14—C15—C10	119.99 (12)
C18—N5—C17	104.42 (12)	C14—C15—C8	133.50 (12)
C3—N1—C1	104.81 (11)	C10—C15—C8	106.43 (12)
C7—N3—C10	108.52 (11)	C2—C1—N1	110.27 (13)
C7—N3—C19	125.61 (12)	C2—C1—H1	124.9
C10—N3—C19	125.58 (12)	N1—C1—H1	124.9
C14—C13—C12	121.06 (12)	C5—C6—C7	118.08 (13)
C14—C13—N4	119.69 (12)	C5—C6—H6	121.0
C12—C13—N4	119.18 (11)	C7—C6—H6	121.0
C6—C5—C4	120.98 (13)	C9—C4—C5	121.53 (13)
C6—C5—H5	119.5	C9—C4—N2	119.89 (12)
C4—C5—H5	119.5	C5—C4—N2	118.56 (12)
C4—C9—C8	118.25 (13)	C17—C16—N4	106.22 (13)
C4—C9—H9	120.9	C17—C16—H16	126.9
C8—C9—H9	120.9	N4—C16—H16	126.9
C11—C12—C13	120.91 (12)	N3—C19—C20	112.98 (14)
C11—C12—H12	119.5	N3—C19—H19A	109.0
C13—C12—H12	119.5	C20—C19—H19A	109.0
N3—C7—C6	129.66 (13)	N3—C19—H19B	109.0
N3—C7—C8	108.93 (12)	C20—C19—H19B	109.0
C6—C7—C8	121.33 (13)	H19A—C19—H19B	107.8
N3—C10—C11	129.53 (13)	N1—C3—N2	112.77 (12)
N3—C10—C15	109.31 (12)	N1—C3—H3	123.6
C11—C10—C15	121.11 (13)	N2—C3—H3	123.6
C12—C11—C10	118.32 (13)	C16—C17—N5	110.75 (13)
C12—C11—H11	120.8	C16—C17—H17	124.6
C10—C11—H11	120.8	N5—C17—H17	124.6
C9—C8—C7	119.82 (12)	C19—C20—H20A	109.5
C9—C8—C15	133.27 (12)	C19—C20—H20B	109.5
C7—C8—C15	106.82 (12)	H20A—C20—H20B	109.5
C13—C14—C15	118.58 (12)	C19—C20—H20C	109.5
C13—C14—H14	120.7	H20A—C20—H20C	109.5
C15—C14—H14	120.7	H20B—C20—H20C	109.5
C1—C2—N2	106.44 (12)
C18—N4—C13—C14	−44.43 (19)	C13—C14—C15—C8	−175.75 (14)
C16—N4—C13—C14	139.43 (14)	N3—C10—C15—C14	−176.74 (11)
C18—N4—C13—C12	132.48 (14)	C11—C10—C15—C14	1.0 (2)
C16—N4—C13—C12	−43.66 (19)	N3—C10—C15—C8	0.35 (15)
C14—C13—C12—C11	0.2 (2)	C11—C10—C15—C8	178.06 (12)
N4—C13—C12—C11	−176.63 (11)	C9—C8—C15—C14	−0.2 (3)
C10—N3—C7—C6	176.82 (13)	C7—C8—C15—C14	176.22 (14)
C19—N3—C7—C6	2.8 (2)	C9—C8—C15—C10	−176.67 (14)
C10—N3—C7—C8	0.07 (15)	C7—C8—C15—C10	−0.30 (15)
C19—N3—C7—C8	−173.96 (13)	N2—C2—C1—N1	0.16 (17)
C7—N3—C10—C11	−177.73 (13)	C3—N1—C1—C2	−0.17 (17)
C19—N3—C10—C11	−3.7 (2)	C4—C5—C6—C7	−0.9 (2)
C7—N3—C10—C15	−0.26 (16)	N3—C7—C6—C5	−175.61 (13)
C19—N3—C10—C15	173.77 (13)	C8—C7—C6—C5	0.8 (2)
C13—C12—C11—C10	1.1 (2)	C8—C9—C4—C5	0.6 (2)
N3—C10—C11—C12	175.49 (13)	C8—C9—C4—N2	−177.63 (11)
C15—C10—C11—C12	−1.7 (2)	C6—C5—C4—C9	0.3 (2)
C4—C9—C8—C7	−0.7 (2)	C6—C5—C4—N2	178.49 (12)
C4—C9—C8—C15	175.30 (14)	C3—N2—C4—C9	55.86 (19)
N3—C7—C8—C9	177.10 (12)	C2—N2—C4—C9	−128.49 (15)
C6—C7—C8—C9	0.0 (2)	C3—N2—C4—C5	−122.38 (15)
N3—C7—C8—C15	0.15 (15)	C2—N2—C4—C5	53.27 (19)
C6—C7—C8—C15	−176.93 (13)	C18—N4—C16—C17	0.40 (16)
C12—C13—C14—C15	−1.0 (2)	C13—N4—C16—C17	177.15 (13)
N4—C13—C14—C15	175.86 (11)	C7—N3—C19—C20	−89.67 (19)
C3—N2—C2—C1	−0.09 (16)	C10—N3—C19—C20	97.30 (19)
C4—N2—C2—C1	−176.48 (13)	C1—N1—C3—N2	0.11 (16)
C17—N5—C18—N4	0.02 (16)	C2—N2—C3—N1	−0.02 (16)
C16—N4—C18—N5	−0.26 (16)	C4—N2—C3—N1	176.39 (12)
C13—N4—C18—N5	−177.10 (12)	N4—C16—C17—N5	−0.41 (18)
C13—C14—C15—C10	0.4 (2)	C18—N5—C17—C16	0.24 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1i	0.93	2.73	3.533 (2)	144
C2—H2···N1ii	0.93	2.63	3.452 (2)	148
C16—H16···N5ii	0.93	2.68	3.509 (2)	149
C14—H14···N5iii	0.93	2.66	3.570 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.93	2.73	3.533 (2)	144
C2—H2⋯N1ii	0.93	2.63	3.452 (2)	148
C16—H16⋯N5ii	0.93	2.68	3.509 (2)	149
C14—H14⋯N5iii	0.93	2.66	3.570 (2)	165

Symmetry codes: (i) ; (ii) ; (iii) .