Download citation
Download citation
link to html
In the title compound, C28H24N2, the carbazole ring systems are essentially planar to within 0.076 (3) Å. The dihedral angle between the planes of the ring systems is 40.38 (4)°. The contribution of inter­molecular π–π inter­actions to the mol­ecular stacking is observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600571X/om2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600571X/om2002Isup2.hkl
Contains datablock I

CCDC reference: 601225

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.135
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.96 Deg.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C28 H24 N2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

9,9'-Diethyl-3,3'-di-9H-carbazolyl top
Crystal data top
C28H24N2Dx = 1.231 Mg m3
Mr = 388.49Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 25 reflections
Hall symbol: -I 4adθ = 5.7–18.4°
a = 22.6201 (8) ŵ = 0.07 mm1
c = 16.3918 (12) ÅT = 295 K
V = 8387.2 (7) Å3Prism, colorless
Z = 160.51 × 0.43 × 0.42 mm
F(000) = 3296
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.5°
Graphite monochromatorh = 026
ω scansk = 026
3689 measured reflectionsl = 019
3689 independent reflections3 standard reflections every 120 min
1481 reflections with I > 2σ(I) intensity decay: 1.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
3689 reflections(Δ/σ)max = 0.004
271 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.14 e Å3
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.6802 (0.0140) x + 22.5186 (0.0019) y + 0.9615 (0.0103) z = 12.1991 (0.0065)

* -0.0123 (0.0025) N * -0.0031 (0.0029) C1 * -0.0048 (0.0029) C2 * 0.0106 (0.0026) C3 * 0.0086 (0.0027) C4 * 0.0064 (0.0030) C4A * -0.0105 (0.0031) C4B * -0.0127 (0.0029) C5 * -0.0065 (0.0028) C6 * 0.0091 (0.0030) C7 * 0.0186 (0.0028) C8 * -0.0017 (0.0030) C8A * -0.0016 (0.0031) C9A

Rms deviation of fitted atoms = 0.0095

13.3016 (0.0111) x + 18.2956 (0.0082) y + 0.0615 (0.0105) z = 17.5082 (0.0040)

Angle to previous plane (with approximate e.s.d.) = 40.38 (0.04)

* 0.0250 (0.0024) N' * 0.0079 (0.0028) C1' * -0.0592 (0.0030) C2' * -0.0723 (0.0027) C3' * 0.0087 (0.0026) C4' * 0.0657 (0.0028) C4A' * 0.0632 (0.0029) C4B' * 0.0464 (0.0028) C5' * -0.0280 (0.0029) C6' * -0.0759 (0.0030) C7' * -0.0414 (0.0029) C8' * 0.0217 (0.0029) C8A' * 0.0382 (0.0028) C9A'

Rms deviation of fitted atoms = 0.0482

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
xyzUiso*/Ueq
N0.47917 (13)0.57308 (12)0.09042 (19)0.0602 (8)
C4A0.44017 (15)0.57645 (14)0.0372 (2)0.0488 (9)
C30.49753 (16)0.58619 (14)0.1606 (2)0.0538 (9)
C40.44327 (16)0.58040 (14)0.1219 (2)0.0551 (9)
H40.40880.57910.15260.066*
C9A'0.50582 (15)0.59272 (14)0.4215 (2)0.0517 (9)
C3'0.50137 (16)0.58934 (15)0.2510 (2)0.0520 (9)
N'0.51554 (12)0.58520 (12)0.50384 (18)0.0562 (8)
C8A'0.56461 (15)0.54938 (15)0.5143 (2)0.0550 (10)
C8A0.41820 (16)0.56865 (14)0.0987 (2)0.0537 (9)
C4B0.39241 (16)0.56967 (14)0.0205 (2)0.0524 (9)
C1'0.46120 (15)0.62337 (15)0.3813 (2)0.0597 (10)
H1'0.43320.64510.41010.072*
C9A0.49256 (16)0.57807 (14)0.0081 (2)0.0536 (9)
C10.54700 (16)0.58362 (15)0.0283 (2)0.0633 (10)
H10.58150.58490.00250.076*
C4'0.54647 (15)0.56112 (13)0.2929 (2)0.0544 (10)
H4'0.57540.54090.26380.065*
C4A'0.54930 (15)0.56246 (13)0.3775 (2)0.0487 (9)
C4B'0.58739 (15)0.53483 (14)0.4372 (2)0.0533 (9)
C10'0.47949 (15)0.61026 (16)0.5683 (2)0.0658 (10)
H10D0.43830.60820.55220.079*
H10C0.48420.58660.61720.079*
C7'0.63792 (17)0.49096 (17)0.5776 (3)0.0737 (11)
H7'0.65520.47550.62450.088*
C5'0.63663 (15)0.49809 (15)0.4316 (2)0.0610 (10)
H5'0.65250.48850.38090.073*
C80.38493 (17)0.56405 (14)0.1694 (2)0.0645 (10)
H80.40280.56410.22040.077*
C20.54849 (16)0.58724 (14)0.1122 (2)0.0593 (10)
H20.5850.59050.13780.071*
C50.33115 (16)0.56523 (14)0.0151 (2)0.0624 (10)
H50.31280.56580.03570.075*
C2'0.45979 (15)0.62044 (15)0.2973 (2)0.0616 (10)
H2'0.42960.64020.27010.074*
C60.29771 (16)0.56002 (15)0.0852 (3)0.0690 (11)
H60.25680.55690.08120.083*
C6'0.66148 (16)0.47620 (17)0.5021 (3)0.0712 (11)
H6'0.69420.45140.49920.085*
C100.52028 (16)0.57848 (18)0.1577 (2)0.0758 (12)
H10A0.55940.56680.13950.091*
H10B0.50850.55180.20110.091*
C8'0.58982 (17)0.52784 (17)0.5853 (2)0.0674 (10)
H8'0.57480.53790.63620.081*
C11'0.49475 (17)0.67331 (16)0.5878 (2)0.0880 (13)
H11D0.46940.68740.63050.132*
H11E0.53520.67560.60530.132*
H11F0.48940.69720.540.132*
C70.32430 (18)0.55945 (15)0.1614 (3)0.0706 (11)
H70.3010.55590.20790.085*
C110.52291 (17)0.64069 (19)0.1907 (2)0.0989 (15)
H11A0.54960.6420.23620.148*
H11B0.48420.65270.2080.148*
H11C0.53670.66690.14880.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.048 (2)0.069 (2)0.063 (2)0.0000 (15)0.0032 (18)0.0023 (17)
C4A0.047 (2)0.045 (2)0.055 (3)0.0055 (17)0.003 (2)0.0006 (18)
C30.051 (2)0.049 (2)0.061 (3)0.0003 (18)0.005 (2)0.001 (2)
C40.058 (3)0.048 (2)0.059 (3)0.0019 (19)0.008 (2)0.0038 (19)
C9A'0.052 (2)0.046 (2)0.058 (3)0.0068 (18)0.001 (2)0.000 (2)
C3'0.048 (2)0.049 (2)0.059 (2)0.0024 (19)0.001 (2)0.002 (2)
N'0.057 (2)0.059 (2)0.052 (2)0.0003 (17)0.0056 (17)0.0034 (17)
C8A'0.055 (2)0.046 (2)0.064 (3)0.003 (2)0.005 (2)0.001 (2)
C8A0.058 (3)0.048 (2)0.055 (3)0.0027 (19)0.006 (2)0.0038 (19)
C4B0.050 (2)0.047 (2)0.060 (3)0.0033 (19)0.000 (2)0.0002 (19)
C1'0.055 (3)0.062 (3)0.062 (3)0.013 (2)0.002 (2)0.002 (2)
C9A0.049 (2)0.059 (2)0.053 (2)0.0015 (19)0.005 (2)0.0029 (19)
C10.054 (3)0.070 (3)0.065 (3)0.003 (2)0.003 (2)0.005 (2)
C4'0.052 (2)0.045 (2)0.066 (3)0.0021 (19)0.004 (2)0.0085 (19)
C4A'0.053 (2)0.040 (2)0.054 (2)0.0077 (19)0.001 (2)0.0014 (19)
C4B'0.048 (2)0.043 (2)0.069 (3)0.0008 (19)0.005 (2)0.001 (2)
C10'0.060 (3)0.071 (3)0.067 (3)0.004 (2)0.004 (2)0.003 (2)
C7'0.067 (3)0.069 (3)0.085 (3)0.006 (2)0.026 (3)0.012 (3)
C5'0.056 (2)0.055 (2)0.072 (3)0.002 (2)0.010 (2)0.001 (2)
C80.066 (3)0.060 (3)0.068 (3)0.007 (2)0.005 (2)0.007 (2)
C20.050 (2)0.064 (3)0.064 (3)0.006 (2)0.003 (2)0.002 (2)
C50.059 (3)0.054 (2)0.074 (3)0.002 (2)0.004 (2)0.013 (2)
C2'0.056 (3)0.055 (2)0.074 (3)0.015 (2)0.003 (2)0.009 (2)
C60.050 (2)0.066 (3)0.091 (3)0.007 (2)0.017 (3)0.011 (3)
C6'0.056 (2)0.067 (3)0.090 (3)0.002 (2)0.009 (3)0.001 (3)
C100.056 (3)0.107 (4)0.064 (3)0.013 (2)0.010 (2)0.005 (3)
C8'0.067 (3)0.072 (3)0.063 (3)0.007 (2)0.012 (2)0.005 (2)
C11'0.088 (3)0.084 (3)0.093 (3)0.006 (3)0.022 (3)0.016 (3)
C70.076 (3)0.065 (3)0.070 (3)0.009 (2)0.014 (3)0.001 (2)
C110.088 (3)0.120 (4)0.089 (3)0.012 (3)0.014 (3)0.020 (3)
Geometric parameters (Å, º) top
N—C9A1.388 (4)C4B'—C5'1.393 (4)
N—C8A1.389 (4)C10'—C11'1.502 (4)
N—C101.448 (4)C10'—H10D0.97
C4A—C41.392 (4)C10'—H10C0.97
C4A—C9A1.399 (4)C7'—C6'1.388 (5)
C4A—C4B1.444 (4)C7'—C8'1.377 (5)
C3—C41.388 (4)C7'—H7'0.93
C3—C21.400 (4)C5'—C6'1.378 (4)
C3—C3'1.485 (4)C5'—H5'0.93
C4—H40.93C8—C71.382 (4)
C9A'—N'1.378 (4)C8—H80.93
C9A'—C1'1.391 (4)C2—H20.93
C9A'—C4A'1.399 (4)C5—C61.380 (4)
C3'—C4'1.386 (4)C5—H50.93
C3'—C2'1.399 (4)C2'—H2'0.93
N'—C8A'1.385 (4)C6—C71.388 (4)
N'—C10'1.450 (4)C6—H60.93
C8A'—C4B'1.403 (4)C6'—H6'0.93
C8A'—C8'1.385 (4)C10—C111.509 (5)
C8A—C81.385 (4)C10—H10A0.97
C8A—C4B1.408 (4)C10—H10B0.97
C4B—C51.392 (4)C8'—H8'0.93
C1'—C2'1.378 (4)C11'—H11D0.96
C1'—H1'0.93C11'—H11E0.96
C9A—C11.374 (4)C11'—H11F0.96
C1—C21.378 (4)C7—H70.93
C1—H10.93C11—H11A0.96
C4'—C4A'1.388 (4)C11—H11B0.96
C4'—H4'0.93C11—H11C0.96
C4A'—C4B'1.446 (4)
C9A—N—C8A108.5 (3)N'—C10'—H10C108.9
C9A—N—C10126.4 (3)C11'—C10'—H10C108.9
C8A—N—C10124.7 (3)H10D—C10'—H10C107.7
C4—C4A—C9A119.0 (3)C6'—C7'—C8'122.0 (4)
C4—C4A—C4B134.2 (3)C6'—C7'—H7'119
C9A—C4A—C4B106.8 (3)C8'—C7'—H7'119
C4—C3—C2118.0 (3)C6'—C5'—C4B'119.0 (4)
C4—C3—C3'120.8 (3)C6'—C5'—H5'120.5
C2—C3—C3'121.1 (3)C4B'—C5'—H5'120.5
C3—C4—C4A120.5 (3)C7—C8—C8A117.8 (4)
C3—C4—H4119.8C7—C8—H8121.1
C4A—C4—H4119.8C8A—C8—H8121.1
N'—C9A'—C1'129.9 (3)C1—C2—C3123.0 (4)
N'—C9A'—C4A'109.4 (3)C1—C2—H2118.5
C1'—C9A'—C4A'120.6 (3)C3—C2—H2118.5
C4'—C3'—C2'117.2 (3)C6—C5—C4B119.9 (4)
C4'—C3'—C3121.0 (3)C6—C5—H5120
C2'—C3'—C3121.8 (3)C4B—C5—H5120
C9A'—N'—C8A'108.7 (3)C1'—C2'—C3'123.4 (3)
C9A'—N'—C10'125.1 (3)C1'—C2'—H2'118.3
C8A'—N'—C10'126.1 (3)C3'—C2'—H2'118.3
N'—C8A'—C4B'108.7 (3)C7—C6—C5120.9 (3)
N'—C8A'—C8'129.8 (4)C7—C6—H6119.6
C4B'—C8A'—C8'121.5 (3)C5—C6—H6119.6
N—C8A—C8128.8 (4)C7'—C6'—C5'120.3 (4)
N—C8A—C4B108.7 (3)C7'—C6'—H6'119.8
C8—C8A—C4B122.5 (3)C5'—C6'—H6'119.8
C5—C4B—C8A118.0 (3)N—C10—C11112.2 (3)
C5—C4B—C4A135.3 (3)N—C10—H10A109.2
C8A—C4B—C4A106.8 (3)C11—C10—H10A109.2
C2'—C1'—C9A'117.8 (3)N—C10—H10B109.2
C2'—C1'—H1'121.1C11—C10—H10B109.2
C9A'—C1'—H1'121.1H10A—C10—H10B107.9
C1—C9A—N128.7 (3)C7'—C8'—C8A'117.5 (4)
C1—C9A—C4A122.1 (3)C7'—C8'—H8'121.2
N—C9A—C4A109.2 (3)C8A'—C8'—H8'121.2
C2—C1—C9A117.4 (4)C10'—C11'—H11D109.5
C2—C1—H1121.3C10'—C11'—H11E109.5
C9A—C1—H1121.3H11D—C11'—H11E109.5
C4A'—C4'—C3'121.3 (3)C10'—C11'—H11F109.5
C4A'—C4'—H4'119.4H11D—C11'—H11F109.5
C3'—C4'—H4'119.4H11E—C11'—H11F109.5
C4'—C4A'—C9A'119.6 (3)C6—C7—C8121.0 (4)
C4'—C4A'—C4B'134.0 (4)C6—C7—H7119.5
C9A'—C4A'—C4B'106.3 (3)C8—C7—H7119.5
C8A'—C4B'—C5'119.6 (3)C10—C11—H11A109.5
C8A'—C4B'—C4A'106.8 (3)C10—C11—H11B109.5
C5'—C4B'—C4A'133.5 (4)H11A—C11—H11B109.5
N'—C10'—C11'113.4 (3)C10—C11—H11C109.5
N'—C10'—H10D108.9H11A—C11—H11C109.5
C11'—C10'—H10D108.9H11B—C11—H11C109.5
C2—C3—C4—C4A0.7 (5)C2'—C3'—C4'—C4A'1.6 (5)
C3'—C3—C4—C4A178.9 (3)C3—C3'—C4'—C4A'178.1 (3)
C9A—C4A—C4—C30.4 (5)C3'—C4'—C4A'—C9A'0.1 (5)
C4B—C4A—C4—C3179.2 (3)C3'—C4'—C4A'—C4B'175.1 (3)
C4—C3—C3'—C4'140.8 (3)N'—C9A'—C4A'—C4'176.5 (3)
C2—C3—C3'—C4'37.3 (5)C1'—C9A'—C4A'—C4'2.6 (5)
C4—C3—C3'—C2'38.9 (5)N'—C9A'—C4A'—C4B'0.2 (4)
C2—C3—C3'—C2'143.0 (3)C1'—C9A'—C4A'—C4B'178.8 (3)
C1'—C9A'—N'—C8A'178.0 (3)N'—C8A'—C4B'—C5'179.0 (3)
C4A'—C9A'—N'—C8A'1.0 (4)C8'—C8A'—C4B'—C5'0.3 (5)
C1'—C9A'—N'—C10'1.3 (6)N'—C8A'—C4B'—C4A'1.1 (4)
C4A'—C9A'—N'—C10'179.8 (3)C8'—C8A'—C4B'—C4A'177.6 (3)
C9A'—N'—C8A'—C4B'1.3 (4)C4'—C4A'—C4B'—C8A'174.9 (3)
C10'—N'—C8A'—C4B'179.5 (3)C9A'—C4A'—C4B'—C8A'0.5 (4)
C9A'—N'—C8A'—C8'177.2 (3)C4'—C4A'—C4B'—C5'2.5 (7)
C10'—N'—C8A'—C8'2.0 (6)C9A'—C4A'—C4B'—C5'177.9 (3)
C9A—N—C8A—C8178.7 (3)C9A'—N'—C10'—C11'82.3 (4)
C10—N—C8A—C85.2 (6)C8A'—N'—C10'—C11'98.6 (4)
C9A—N—C8A—C4B1.1 (4)C8A'—C4B'—C5'—C6'0.8 (5)
C10—N—C8A—C4B174.6 (3)C4A'—C4B'—C5'—C6'176.3 (3)
N—C8A—C4B—C5179.5 (3)N—C8A—C8—C7179.2 (3)
C8—C8A—C4B—C50.7 (5)C4B—C8A—C8—C71.0 (5)
N—C8A—C4B—C4A1.4 (4)C9A—C1—C2—C30.8 (5)
C8—C8A—C4B—C4A178.4 (3)C4—C3—C2—C10.9 (5)
C4—C4A—C4B—C51.1 (7)C3'—C3—C2—C1179.1 (3)
C9A—C4A—C4B—C5180.0 (4)C8A—C4B—C5—C60.0 (5)
C4—C4A—C4B—C8A180.0 (4)C4A—C4B—C5—C6178.8 (3)
C9A—C4A—C4B—C8A1.1 (4)C9A'—C1'—C2'—C3'1.3 (6)
N'—C9A'—C1'—C2'175.7 (3)C4'—C3'—C2'—C1'1.0 (5)
C4A'—C9A'—C1'—C2'3.1 (5)C3—C3'—C2'—C1'178.6 (3)
C8A—N—C9A—C1179.8 (3)C4B—C5—C6—C70.3 (5)
C10—N—C9A—C16.5 (6)C8'—C7'—C6'—C5'0.5 (6)
C8A—N—C9A—C4A0.4 (4)C4B'—C5'—C6'—C7'0.4 (5)
C10—N—C9A—C4A173.7 (3)C9A—N—C10—C1193.1 (4)
C4—C4A—C9A—C10.2 (5)C8A—N—C10—C1179.2 (4)
C4B—C4A—C9A—C1179.3 (3)C6'—C7'—C8'—C8A'1.0 (5)
C4—C4A—C9A—N179.6 (3)N'—C8A'—C8'—C7'177.7 (3)
C4B—C4A—C9A—N0.5 (4)C4B'—C8A'—C8'—C7'0.6 (5)
N—C9A—C1—C2179.3 (3)C5—C6—C7—C80.0 (6)
C4A—C9A—C1—C20.4 (5)C8A—C8—C7—C60.6 (5)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds