9-Ethyl-3-(imidazo[1,2-a]pyrimidin-3-yl)-9H-carbazole.

The title compound, C(20)H(16)N(4), is a precursor for the production of electron-transporting and -emitting materials. The bond lengths and angles in this compound are normal. In the crystal structure, there are no significant hydrogen-bonding inter-actions or π-π stacking inter-actions between mol-ecules.

Related literature

For general background to the use of small organic molecules or organic polymers as electroluminescent materials, see: Burroughes et al. (1990 ▶); Tang & VanSlyke (1987 ▶).

Experimental

Crystal data

C20H16N4

M = 312.37

Monoclinic,

a = 13.9106 (3) Å

b = 9.3187 (2) Å

c = 12.9047 (3) Å

β = 112.712 (1)°

V = 1543.10 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100.0 (1) K

0.36 × 0.32 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

11748 measured reflections

2717 independent reflections

1991 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 0.91

2717 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.19 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038300/ww2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038300/ww2131Isup2.hkl

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

C20H16N4	F000 = 656
Mr = 312.37	Dx = 1.345 Mg m−3Dm = 1.345 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3698 reflections
a = 13.9106 (3) Å	θ = 2.7–30.2º
b = 9.3187 (2) Å	µ = 0.08 mm−1
c = 12.9047 (3) Å	T = 100.0 (1) K
β = 112.712 (1)º	Prism, yellow
V = 1543.10 (6) Å3	0.36 × 0.32 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Monochromator: graphite	θmax = 25.0º
T = 100.0(1) K	θmin = 1.6º
ω and φ scans	h = −16→16
Absorption correction: none	k = −11→11
11748 measured reflections	l = −15→15
2717 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072	(Δ/σ)max = 0.001
S = 0.91	Δρmax = 0.19 e Å−3
2717 reflections	Δρmin = −0.18 e Å−3
218 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: 0.0063 (8)
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.

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
N4	1.35147 (8)	0.58921 (11)	0.45030 (9)	0.0200 (3)
N3	0.96458 (8)	0.19984 (11)	0.66711 (9)	0.0225 (3)
N1	0.85050 (8)	0.05126 (11)	0.51971 (9)	0.0209 (3)
N2	0.98239 (8)	0.20433 (11)	0.50125 (8)	0.0166 (3)
C17	1.37034 (10)	0.48850 (14)	0.38158 (10)	0.0196 (3)
C16	1.43492 (10)	0.49764 (15)	0.32235 (11)	0.0256 (3)
H16	1.4741	0.5797	0.3258	0.031*
C14	1.43902 (10)	0.38125 (15)	0.25828 (11)	0.0279 (4)
H14	1.4817	0.3852	0.2179	0.033*
C13	1.38043 (10)	0.25737 (15)	0.25257 (11)	0.0253 (3)
H13	1.3845	0.1805	0.2085	0.030*
C12	1.31683 (10)	0.24836 (14)	0.31163 (11)	0.0210 (3)
H12	1.2784	0.1656	0.3081	0.025*
C11	1.31059 (9)	0.36437 (13)	0.37670 (10)	0.0179 (3)
C10	1.25171 (9)	0.39349 (13)	0.44510 (10)	0.0166 (3)
C9	1.17866 (9)	0.31495 (13)	0.47090 (10)	0.0171 (3)
H9	1.1602	0.2230	0.4422	0.021*
C8	1.13349 (9)	0.37494 (13)	0.53988 (10)	0.0171 (3)
C7	1.16524 (10)	0.51203 (13)	0.58548 (10)	0.0195 (3)
H7	1.1364	0.5503	0.6336	0.023*
C24	1.23750 (10)	0.59182 (14)	0.56155 (10)	0.0203 (3)
H24	1.2575	0.6824	0.5927	0.024*
C23	1.27953 (9)	0.53254 (13)	0.48938 (10)	0.0180 (3)
C18	1.39561 (10)	0.73286 (13)	0.47180 (11)	0.0248 (3)
H18A	1.4685	0.7281	0.4827	0.030*
H18B	1.3919	0.7690	0.5406	0.030*
C19	1.33998 (11)	0.83644 (15)	0.37712 (12)	0.0305 (4)
H19A	1.3718	0.9294	0.3954	0.046*
H19B	1.2680	0.8430	0.3668	0.046*
H19C	1.3449	0.8025	0.3091	0.046*
C6	1.04213 (10)	0.29149 (14)	0.66997 (11)	0.0223 (3)
H6	1.0810	0.3451	0.7331	0.027*
C4	0.92857 (10)	0.14710 (13)	0.56400 (10)	0.0181 (3)
C1	0.82339 (10)	0.02090 (13)	0.41227 (11)	0.0214 (3)
H1	0.7709	−0.0464	0.3802	0.026*
C2	0.86906 (10)	0.08412 (13)	0.34325 (11)	0.0205 (3)
H2	0.8445	0.0624	0.2671	0.025*
C3	0.94900 (10)	0.17667 (13)	0.38901 (10)	0.0184 (3)
H3	0.9804	0.2203	0.3453	0.022*
C5	1.05729 (10)	0.29722 (13)	0.57133 (10)	0.0173 (3)

	U11	U22	U33	U12	U13	U23
N4	0.0182 (6)	0.0194 (6)	0.0212 (6)	−0.0032 (5)	0.0064 (5)	0.0020 (5)
N3	0.0221 (6)	0.0286 (7)	0.0179 (6)	−0.0029 (5)	0.0090 (5)	−0.0014 (5)
N1	0.0186 (6)	0.0214 (6)	0.0225 (7)	−0.0001 (5)	0.0076 (5)	0.0002 (5)
N2	0.0167 (6)	0.0193 (6)	0.0148 (6)	0.0011 (5)	0.0071 (5)	0.0008 (5)
C17	0.0145 (7)	0.0257 (8)	0.0166 (7)	0.0018 (6)	0.0038 (6)	0.0037 (6)
C16	0.0167 (7)	0.0315 (8)	0.0279 (8)	−0.0014 (6)	0.0077 (7)	0.0065 (7)
C14	0.0189 (8)	0.0413 (9)	0.0273 (8)	0.0068 (7)	0.0131 (7)	0.0075 (7)
C13	0.0199 (8)	0.0338 (9)	0.0225 (8)	0.0065 (7)	0.0087 (6)	0.0006 (7)
C12	0.0164 (7)	0.0244 (8)	0.0205 (7)	0.0019 (6)	0.0054 (6)	0.0029 (6)
C11	0.0138 (7)	0.0219 (7)	0.0161 (7)	0.0021 (6)	0.0038 (6)	0.0032 (6)
C10	0.0151 (7)	0.0194 (7)	0.0130 (7)	0.0022 (6)	0.0030 (6)	0.0023 (6)
C9	0.0178 (7)	0.0164 (7)	0.0145 (7)	−0.0006 (6)	0.0033 (6)	0.0006 (6)
C8	0.0159 (7)	0.0206 (7)	0.0129 (7)	0.0015 (6)	0.0034 (6)	0.0021 (6)
C7	0.0207 (7)	0.0228 (7)	0.0146 (7)	0.0040 (6)	0.0065 (6)	0.0006 (6)
C24	0.0219 (7)	0.0167 (7)	0.0181 (7)	0.0001 (6)	0.0032 (6)	−0.0008 (6)
C23	0.0157 (7)	0.0200 (7)	0.0158 (7)	0.0007 (6)	0.0033 (6)	0.0050 (6)
C18	0.0229 (8)	0.0214 (8)	0.0284 (8)	−0.0050 (6)	0.0081 (6)	0.0026 (6)
C19	0.0288 (9)	0.0284 (8)	0.0367 (9)	0.0029 (7)	0.0152 (7)	0.0085 (7)
C6	0.0211 (7)	0.0286 (8)	0.0171 (7)	−0.0035 (6)	0.0072 (6)	−0.0041 (6)
C4	0.0184 (7)	0.0213 (7)	0.0166 (7)	0.0019 (6)	0.0090 (6)	0.0031 (6)
C1	0.0180 (7)	0.0207 (7)	0.0229 (8)	0.0011 (6)	0.0051 (6)	−0.0020 (6)
C2	0.0192 (7)	0.0238 (8)	0.0165 (7)	0.0020 (6)	0.0048 (6)	−0.0021 (6)
C3	0.0188 (7)	0.0226 (8)	0.0141 (7)	0.0045 (6)	0.0068 (6)	0.0013 (6)
C5	0.0160 (7)	0.0193 (7)	0.0157 (7)	0.0008 (6)	0.0049 (6)	−0.0014 (6)

N4—C17	1.3841 (16)	C10—C23	1.4088 (17)
N4—C23	1.3871 (15)	C9—C8	1.3898 (16)
N4—C18	1.4541 (15)	C9—H9	0.9300
N3—C4	1.3222 (16)	C8—C7	1.4045 (17)
N3—C6	1.3652 (16)	C8—C5	1.4646 (17)
N1—C1	1.3194 (15)	C7—C24	1.3778 (17)
N1—C4	1.3508 (16)	C7—H7	0.9300
N2—C3	1.3640 (15)	C24—C23	1.3911 (17)
N2—C5	1.3874 (15)	C24—H24	0.9300
N2—C4	1.4031 (15)	C18—C19	1.5143 (18)
C17—C16	1.3889 (17)	C18—H18A	0.9700
C17—C11	1.4115 (17)	C18—H18B	0.9700
C16—C14	1.3782 (18)	C19—H19A	0.9600
C16—H16	0.9300	C19—H19B	0.9600
C14—C13	1.3986 (18)	C19—H19C	0.9600
C14—H14	0.9300	C6—C5	1.3693 (16)
C13—C12	1.3752 (17)	C6—H6	0.9300
C13—H13	0.9300	C1—C2	1.4074 (17)
C12—C11	1.3920 (17)	C1—H1	0.9300
C12—H12	0.9300	C2—C3	1.3499 (18)
C11—C10	1.4429 (16)	C2—H2	0.9300
C10—C9	1.3929 (16)	C3—H3	0.9300
C17—N4—C23	108.46 (10)	C8—C7—H7	118.8
C17—N4—C18	125.16 (10)	C7—C24—C23	117.87 (12)
C23—N4—C18	126.29 (11)	C7—C24—H24	121.1
C4—N3—C6	104.37 (10)	C23—C24—H24	121.1
C1—N1—C4	116.31 (11)	N4—C23—C24	129.87 (12)
C3—N2—C5	132.23 (10)	N4—C23—C10	109.06 (10)
C3—N2—C4	120.15 (11)	C24—C23—C10	121.07 (11)
C5—N2—C4	107.14 (10)	N4—C18—C19	112.72 (11)
N4—C17—C16	129.35 (12)	N4—C18—H18A	109.0
N4—C17—C11	109.28 (10)	C19—C18—H18A	109.0
C16—C17—C11	121.37 (12)	N4—C18—H18B	109.0
C14—C16—C17	117.86 (13)	C19—C18—H18B	109.0
C14—C16—H16	121.1	H18A—C18—H18B	107.8
C17—C16—H16	121.1	C18—C19—H19A	109.5
C16—C14—C13	121.53 (13)	C18—C19—H19B	109.5
C16—C14—H14	119.2	H19A—C19—H19B	109.5
C13—C14—H14	119.2	C18—C19—H19C	109.5
C12—C13—C14	120.51 (13)	H19A—C19—H19C	109.5
C12—C13—H13	119.7	H19B—C19—H19C	109.5
C14—C13—H13	119.7	N3—C6—C5	113.76 (11)
C13—C12—C11	119.36 (12)	N3—C6—H6	123.1
C13—C12—H12	120.3	C5—C6—H6	123.1
C11—C12—H12	120.3	N3—C4—N1	127.00 (11)
C12—C11—C17	119.38 (11)	N3—C4—N2	111.12 (11)
C12—C11—C10	134.22 (12)	N1—C4—N2	121.88 (11)
C17—C11—C10	106.39 (11)	N1—C1—C2	124.03 (12)
C9—C10—C23	119.86 (11)	N1—C1—H1	118.0
C9—C10—C11	133.33 (12)	C2—C1—H1	118.0
C23—C10—C11	106.80 (10)	C3—C2—C1	119.18 (12)
C8—C9—C10	119.59 (12)	C3—C2—H2	120.4
C8—C9—H9	120.2	C1—C2—H2	120.4
C10—C9—H9	120.2	C2—C3—N2	118.06 (12)
C9—C8—C7	119.17 (12)	C2—C3—H3	121.0
C9—C8—C5	122.22 (11)	N2—C3—H3	121.0
C7—C8—C5	118.54 (11)	C6—C5—N2	103.61 (10)
C24—C7—C8	122.38 (12)	C6—C5—C8	131.65 (12)
C24—C7—H7	118.8	N2—C5—C8	124.72 (11)