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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3245.
Published online 2010 November 20. doi:  10.1107/S1600536810047197
PMCID: PMC3011667

(9H-Carbazol-9-ylmeth­yl)diethyl­amine

Abstract

The asymmetric unit of the title compound, C17H20N2, contains two mol­ecules, whose bond lengths and angles differ only slightly. In the crystal, neighbouring mol­ecules form pillar structures via edge-to-face π–π stacking inter­actions [edge-to-face distances = 3.538 (3) and 3.496 (3)Å].

Related literature

Carbazole-based compounds are widely used in OLEDs as emitters because of their intense luminescence, see: Adhikari et al. (2007 [triangle]); Liu et al. (2006 [triangle]); Palayangoda et al. (2008 [triangle]) and as organic fluorescence probes, see: Hao et al. (2010 [triangle]); Pappayee & Mishra, (2000 [triangle]). For our studies of organic fluorescence probes, see: Shen et al. (2006 [triangle], 2008 [triangle]). For the preparation of the title compound, see: Gu et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3245-scheme1.jpg

Experimental

Crystal data

  • C17H20N2
  • M r = 252.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3245-efi3.jpg
  • a = 24.338 (2) Å
  • b = 6.3216 (11) Å
  • c = 19.133 (2) Å
  • β = 104.109 (2)°
  • V = 2854.9 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 291 K
  • 0.28 × 0.24 × 0.22 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.981, T max = 0.985
  • 13429 measured reflections
  • 5463 independent reflections
  • 3052 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.120
  • S = 1.06
  • 5463 reflections
  • 347 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008) [triangle]; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047197/hg2745sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047197/hg2745Isup2.hkl

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

Acknowledgments

We thank the Natural Science Foundation of Jiangsu Province, China (grant No. BK2008435) and the National Natural Science Foundation of China (grant No. 20771060) for financial support.

supplementary crystallographic information

Comment

Carbazole-based compounds are known for their intense luminescence and widely used in OLEDs as emitters (Adhikari et al., 2007; Liu et al., 2006; Palayangoda et al., 2008). They can also be used as organic fluorescence probes (Hao et al., 2010; Pappayee et al., 2000). In our continuing studies in organic fluorescence probes (Shen et al., 2008; Shen et al., 2006), the 9-diethylaminomethyl carbazole(I) was synthesized.

The crystal structure of the title compound, C17H20N2, reveals that all the bond lengths and angles have normal values. Each asymmetric unit contains two title molecules, which are similar to each other with only slightly difference in their bond lengths and angles (Figure 1 and Table 1).

In the crystal packing the edge-to-face π–π stacking interactions were observed. The distance from the edge of the molecular plane B (N1i/C1i/C2i/C3i/C4i/C5i/C6i/C7i/C8i/C9i/ C10i/C11i/C12i)(i: 1 - x,-1/2 + y,0.5 - z) to the face of the molecular plane A(N1/C1/C2/C3/C4/C5/C6/C7/C8/C9/C10/C11/C12) is 3.538 (3) Å, and the dihedral angle between plane A and B is 62.06 (3)°. Similar relationships were observed with the molecular plane C and D. The edge-to-face distance of the molecular plane D(N3ii/C18ii/C19ii/C20ii/C21ii/C22ii/C23ii/ C24ii/C25ii/C26ii/C27ii/C28ii/C29ii)(ii: -x,1/2 + y,0.5 - z) to the molecular plane C(N3/C18/C19/C20/C21/C22/C23/C24/C25/C26/C27 /C28/C29) is 3.496 (3) Å, and the dihedral angle between plane C and D is 61.41 (3)° (Figure 2).Through these edge-to-face π–π stacking interactions, the neighbouring molecules form pillar structures (Figure 3).

Experimental

9-Diethylaminomethyl carbazole was prepared according to a procedure described in the literature (Gu, et al., 1997). Colorless crystals were obtained by recrystallized from ethanol at room temperature.

1H-NMR (CDCl3, 400 MHz) δ: 1.07 (t, 6H, 2-CH3), 2.68 (q, 4H, 2-CH2-), 4.98 (s, 2H, –CH2-), 7.22 (t, 2H, ArH), 7.44 (t, 2H, ArH), 7.54 (d, 2H, ArH), 8.06 (d, 2H, ArH).

Refinement

The H atoms were placed in calculated positions and included as part of a riding model, with C—H = 0.93–0.97 Å, and with Uequiv values set at 1.2 Uequiv of the parent atoms.

Figures

Fig. 1.
A view of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at 30% probability level. All H atoms have been omitted for clarity.
Fig. 2.
A view of the edge-to-face π–π stacking interactions. Dashed lines indicate weqk edge-to-face π–π stacking interactions and all H atoms have been omitted for clarity. (i: 1 - x,-1/2 + y,0.5 - z ii: -x,1/2 ...
Fig. 3.
A view of the pillar structure. Dashed lines indicate weak edge-to-face π–π stacking interactions. All H atoms have been omitted for clarity. (i: 1 - x,-1/2 + y,0.5 - z ii: -x,1/2 + y,0.5 - z)

Crystal data

C17H20N2F(000) = 1088
Mr = 252.35Dx = 1.174 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1470 reflections
a = 24.338 (2) Åθ = 2.2–21.0°
b = 6.3216 (11) ŵ = 0.07 mm1
c = 19.133 (2) ÅT = 291 K
β = 104.109 (2)°Block, colourless
V = 2854.9 (6) Å30.28 × 0.24 × 0.22 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer5463 independent reflections
Radiation source: sealed tube3052 reflections with I > 2σ(I)
graphiteRint = 0.039
phi and ω scansθmax = 26.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −25→29
Tmin = 0.981, Tmax = 0.985k = −7→7
13429 measured reflectionsl = −22→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
5463 reflections(Δ/σ)max < 0.001
347 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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)8.9285(0.0063)x - 3.2585(0.0028)y + 12.6587(0.0061)z = 2.4983(0.0046)* -0.0251 (0.0014) N1 * -0.0167 (0.0017) C1 * 0.0499 (0.0017) C2 * 0.0607 (0.0018) C3 * -0.0014 (0.0018) C4 * -0.0354 (0.0017) C5 * -0.0486 (0.0017) C6 * -0.0407 (0.0017) C7 * 0.0096 (0.0017) C8 * 0.0577 (0.0017) C9 * 0.0343 (0.0017) C10 * -0.0110 (0.0016) C11 * -0.0333 (0.0017) C12Rms deviation of fitted atoms = 0.03748.9285(0.0063)x + 3.2585(0.0028)y + 12.6588(0.0061)z = 11.1303(0.0032)Angle to previous plane (with approximate e.s.d.) = 62.06 (0.03)* 0.0251 (0.0014) N1_$1 * 0.0167 (0.0017) C1_$1 * -0.0499 (0.0017) C2_$1 * -0.0607 (0.0018) C3_$1 * 0.0014 (0.0018) C4_$1 * 0.0354 (0.0017) C5_$1 * 0.0486 (0.0017) C6_$1 * 0.0407 (0.0017) C7_$1 * -0.0096 (0.0017) C8_$1 * -0.0577 (0.0017) C9_$1 * -0.0343 (0.0017) C10_$1 * 0.0110 (0.0016) C11_$1 * 0.0333 (0.0017) C12_$1Rms deviation of fitted atoms = 0.0374-17.1148(0.0065)x + 3.2280(0.0027)y + 12.4596(0.0056)z = 1.3402(0.0013)Angle to previous plane (with approximate e.s.d.) = 67.15 (0.03)* -0.0095 (0.0014) N3 * -0.0154 (0.0016) C18 * -0.0081 (0.0017) C19 * 0.0048 (0.0018) C20 * 0.0356 (0.0017) C21 * 0.0196 (0.0016) C22 * -0.0218 (0.0017) C23 * -0.0287 (0.0017) C24 * -0.0272 (0.0016) C25 * -0.0051 (0.0017) C26 * 0.0333 (0.0018) C27 * 0.0347 (0.0016) C28 * -0.0123 (0.0016) C29Rms deviation of fitted atoms = 0.0225-17.1148(0.0065)x - 3.2280(0.0027)y + 12.4596(0.0056)z = 3.2755(0.0028)Angle to previous plane (with approximate e.s.d.) = 61.41 (0.03)* 0.0095 (0.0014) N3_$2 * 0.0154 (0.0016) C18_$2 * 0.0081 (0.0017) C19_$2 * -0.0048 (0.0018) C20_$2 * -0.0356 (0.0017) C21_$2 * -0.0196 (0.0016) C22_$2 * 0.0218 (0.0017) C23_$2 * 0.0287 (0.0017) C24_$2 * 0.0272 (0.0016) C25_$2 * 0.0051 (0.0017) C26_$2 * -0.0333 (0.0018) C27_$2 * -0.0347 (0.0016) C28_$2 * 0.0123 (0.0016) C29_$2Rms deviation of fitted atoms = 0.0225
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)

xyzUiso*/Ueq
C10.36426 (8)0.9208 (3)0.17614 (10)0.0376 (4)
C20.31632 (9)0.8391 (4)0.19419 (11)0.0458 (5)
H20.30060.71120.17520.055*
C30.29289 (10)0.9544 (4)0.24125 (11)0.0539 (6)
H30.26100.90270.25430.065*
C40.31618 (11)1.1462 (4)0.26928 (12)0.0580 (6)
H40.29901.22260.29960.070*
C50.36412 (10)1.2249 (3)0.25303 (10)0.0469 (5)
H50.37991.35130.27330.056*
C60.38897 (8)1.1136 (3)0.20581 (10)0.0395 (5)
C70.43876 (9)1.1426 (3)0.17880 (10)0.0380 (5)
C80.48144 (10)1.2920 (3)0.19114 (11)0.0440 (5)
H80.48041.40630.22140.053*
C90.52563 (9)1.2705 (3)0.15822 (12)0.0489 (6)
H90.55471.36980.16710.059*
C100.52730 (9)1.1005 (3)0.11143 (12)0.0471 (5)
H100.55701.09000.08890.057*
C110.48519 (9)0.9490 (3)0.09856 (10)0.0413 (5)
H110.48600.83600.06770.050*
C120.44188 (8)0.9704 (3)0.13283 (10)0.0363 (4)
C130.38250 (9)0.6526 (3)0.08628 (10)0.0390 (5)
H13A0.35190.57590.09930.047*
H13B0.41530.56010.09460.047*
C140.31317 (9)0.8340 (3)−0.00586 (11)0.0422 (5)
H14A0.31630.94320.03050.051*
H14B0.28170.7431−0.00280.051*
C150.30047 (10)0.9368 (3)−0.07941 (11)0.0494 (5)
H15A0.33291.0161−0.08460.074*
H15B0.26861.0299−0.08440.074*
H15C0.29190.8295−0.11600.074*
C160.35944 (9)0.5149 (3)−0.03411 (11)0.0446 (5)
H16A0.34320.5523−0.08410.054*
H16B0.33310.4205−0.01900.054*
C170.41427 (9)0.3987 (3)−0.02917 (12)0.0468 (5)
H17A0.44360.4985−0.03110.070*
H17B0.40980.3016−0.06870.070*
H17C0.42440.32200.01540.070*
C180.04584 (8)0.0516 (3)0.15594 (10)0.0351 (4)
C190.00476 (9)0.0810 (4)0.09248 (11)0.0446 (5)
H190.00560.19760.06310.053*
C20−0.03736 (9)−0.0685 (4)0.07439 (12)0.0520 (6)
H20−0.0650−0.05310.03150.062*
C21−0.04000 (9)−0.2432 (4)0.11849 (12)0.0522 (6)
H21−0.0696−0.33970.10530.063*
C220.00128 (8)−0.2722 (3)0.18142 (11)0.0436 (5)
H22−0.0001−0.38810.21090.052*
C230.04508 (8)−0.1255 (3)0.20027 (10)0.0364 (4)
C240.09355 (8)−0.1064 (3)0.26133 (10)0.0365 (4)
C250.11486 (9)−0.2287 (4)0.32240 (11)0.0446 (5)
H250.0971−0.35440.32950.054*
C260.16223 (9)−0.1619 (4)0.37195 (11)0.0503 (6)
H260.1768−0.24430.41250.060*
C270.18903 (9)0.0279 (4)0.36267 (11)0.0494 (5)
H270.22090.07080.39730.059*
C280.16878 (9)0.1523 (3)0.30273 (11)0.0431 (5)
H280.18650.27910.29680.052*
C290.12153 (8)0.0847 (3)0.25158 (10)0.0343 (4)
C300.10458 (9)0.3792 (3)0.15881 (11)0.0409 (5)
H30A0.12890.46080.19710.049*
H30B0.06940.45690.14220.049*
C310.12229 (10)0.5486 (4)0.05375 (12)0.0543 (6)
H31A0.08190.57570.03970.065*
H31B0.13450.51860.01010.065*
C320.15171 (11)0.7484 (3)0.08706 (14)0.0623 (7)
H32A0.14100.77850.13110.093*
H32B0.14080.86430.05420.093*
H32C0.19200.72920.09700.093*
C330.19210 (9)0.3007 (3)0.12612 (12)0.0464 (5)
H33A0.19460.17250.15460.056*
H33B0.21130.41220.15760.056*
C340.22266 (11)0.2653 (4)0.06688 (14)0.0658 (7)
H34A0.20160.16670.03240.099*
H34B0.25980.20940.08740.099*
H34C0.22590.39720.04340.099*
N10.39612 (7)0.8375 (2)0.13156 (8)0.0365 (4)
N20.36559 (6)0.7080 (2)0.00993 (8)0.0359 (4)
N30.09245 (7)0.1786 (2)0.18752 (8)0.0353 (4)
N40.13199 (7)0.3584 (2)0.09955 (9)0.0391 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0431 (11)0.0382 (10)0.0286 (9)0.0088 (9)0.0031 (8)0.0040 (8)
C20.0447 (12)0.0515 (13)0.0404 (11)0.0040 (10)0.0085 (10)0.0047 (10)
C30.0502 (13)0.0698 (16)0.0412 (12)0.0061 (12)0.0100 (11)0.0061 (11)
C40.0629 (15)0.0736 (17)0.0377 (12)0.0200 (14)0.0129 (11)−0.0067 (12)
C50.0649 (15)0.0367 (11)0.0328 (10)0.0090 (10)−0.0003 (11)−0.0009 (9)
C60.0433 (11)0.0376 (11)0.0311 (9)0.0080 (9)−0.0037 (9)0.0007 (8)
C70.0425 (11)0.0332 (10)0.0303 (10)0.0068 (9)−0.0062 (8)0.0003 (8)
C80.0568 (13)0.0342 (10)0.0335 (10)0.0041 (10)−0.0032 (10)−0.0009 (8)
C90.0454 (12)0.0396 (11)0.0527 (13)−0.0095 (10)−0.0056 (11)0.0034 (10)
C100.0382 (11)0.0453 (12)0.0540 (13)−0.0005 (10)0.0036 (10)−0.0018 (10)
C110.0440 (11)0.0342 (11)0.0423 (11)0.0037 (9)0.0038 (10)−0.0023 (9)
C120.0346 (10)0.0307 (10)0.0384 (10)0.0082 (8)−0.0011 (8)0.0021 (8)
C130.0434 (11)0.0300 (9)0.0415 (11)0.0006 (9)0.0059 (9)−0.0054 (9)
C140.0420 (11)0.0409 (11)0.0405 (11)0.0065 (9)0.0039 (10)0.0005 (9)
C150.0531 (13)0.0404 (11)0.0490 (12)−0.0012 (10)0.0015 (10)0.0074 (9)
C160.0457 (12)0.0346 (10)0.0504 (11)0.0004 (9)0.0057 (10)−0.0151 (9)
C170.0482 (13)0.0360 (11)0.0533 (13)0.0020 (9)0.0071 (10)−0.0125 (9)
C180.0368 (10)0.0385 (10)0.0329 (9)0.0014 (8)0.0144 (9)−0.0014 (8)
C190.0453 (12)0.0541 (12)0.0358 (10)0.0013 (11)0.0126 (9)−0.0022 (9)
C200.0386 (12)0.0752 (16)0.0411 (11)0.0002 (11)0.0074 (10)−0.0129 (11)
C210.0415 (12)0.0636 (15)0.0562 (13)−0.0151 (11)0.0209 (11)−0.0211 (12)
C220.0447 (12)0.0429 (11)0.0499 (12)−0.0078 (10)0.0246 (11)−0.0083 (9)
C230.0372 (10)0.0412 (11)0.0350 (10)0.0002 (9)0.0168 (9)−0.0025 (9)
C240.0407 (11)0.0371 (10)0.0360 (10)0.0031 (9)0.0175 (9)−0.0021 (9)
C250.0480 (13)0.0478 (12)0.0436 (11)0.0107 (10)0.0216 (11)0.0070 (10)
C260.0487 (13)0.0693 (15)0.0370 (12)0.0180 (12)0.0180 (10)0.0081 (10)
C270.0374 (11)0.0752 (16)0.0353 (10)0.0007 (11)0.0080 (9)−0.0005 (11)
C280.0456 (12)0.0472 (12)0.0405 (11)−0.0020 (10)0.0180 (10)−0.0077 (9)
C290.0363 (10)0.0382 (10)0.0314 (9)0.0026 (8)0.0139 (8)0.0008 (8)
C300.0459 (11)0.0278 (10)0.0530 (12)0.0014 (9)0.0194 (10)−0.0005 (9)
C310.0524 (13)0.0558 (14)0.0514 (13)−0.0038 (11)0.0060 (11)0.0236 (11)
C320.0694 (17)0.0346 (12)0.0866 (18)0.0006 (11)0.0263 (14)0.0193 (12)
C330.0524 (13)0.0381 (11)0.0531 (13)0.0045 (10)0.0214 (11)0.0052 (9)
C340.0804 (19)0.0502 (14)0.0831 (18)0.0030 (13)0.0516 (16)0.0091 (13)
N10.0406 (9)0.0327 (8)0.0347 (9)0.0007 (7)0.0065 (7)−0.0038 (7)
N20.0356 (8)0.0309 (8)0.0367 (9)0.0040 (7)0.0003 (7)−0.0064 (7)
N30.0428 (9)0.0309 (8)0.0344 (8)−0.0010 (7)0.0135 (7)0.0030 (6)
N40.0481 (10)0.0327 (9)0.0389 (9)0.0014 (7)0.0151 (8)0.0065 (7)

Geometric parameters (Å, °)

C1—N11.389 (2)C18—C191.384 (3)
C1—C21.394 (3)C18—N31.401 (2)
C1—C61.415 (3)C18—C231.408 (3)
C2—C31.385 (3)C19—C201.375 (3)
C2—H20.9300C19—H190.9300
C3—C41.389 (3)C20—C211.401 (3)
C3—H30.9300C20—H200.9300
C4—C51.372 (3)C21—C221.380 (3)
C4—H40.9300C21—H210.9300
C5—C61.394 (3)C22—C231.392 (3)
C5—H50.9300C22—H220.9300
C6—C71.440 (3)C23—C241.449 (3)
C7—C81.381 (3)C24—C251.392 (3)
C7—C121.413 (3)C24—C291.421 (3)
C8—C91.379 (3)C25—C261.369 (3)
C8—H80.9300C25—H250.9300
C9—C101.406 (3)C26—C271.398 (3)
C9—H90.9300C26—H260.9300
C10—C111.380 (3)C27—C281.379 (3)
C10—H100.9300C27—H270.9300
C11—C121.377 (3)C28—C291.384 (3)
C11—H110.9300C28—H280.9300
C12—N11.390 (2)C29—N31.390 (2)
C13—N11.445 (2)C30—N31.440 (2)
C13—N21.460 (2)C30—N41.455 (2)
C13—H13A0.9700C30—H30A0.9700
C13—H13B0.9700C30—H30B0.9700
C14—N21.471 (2)C31—N41.473 (3)
C14—C151.512 (3)C31—C321.514 (3)
C14—H14A0.9700C31—H31A0.9700
C14—H14B0.9700C31—H31B0.9700
C15—H15A0.9600C32—H32A0.9600
C15—H15B0.9600C32—H32B0.9600
C15—H15C0.9600C32—H32C0.9600
C16—N21.470 (2)C33—N41.473 (3)
C16—C171.506 (3)C33—C341.516 (3)
C16—H16A0.9700C33—H33A0.9700
C16—H16B0.9700C33—H33B0.9700
C17—H17A0.9600C34—H34A0.9600
C17—H17B0.9600C34—H34B0.9600
C17—H17C0.9600C34—H34C0.9600
N1—C1—C2129.63 (19)C19—C20—C21122.1 (2)
N1—C1—C6109.08 (18)C19—C20—H20119.0
C2—C1—C6121.27 (19)C21—C20—H20119.0
C3—C2—C1117.9 (2)C22—C21—C20120.0 (2)
C3—C2—H2121.0C22—C21—H21120.0
C1—C2—H2121.0C20—C21—H21120.0
C2—C3—C4121.1 (2)C21—C22—C23119.1 (2)
C2—C3—H3119.5C21—C22—H22120.4
C4—C3—H3119.5C23—C22—H22120.4
C5—C4—C3121.2 (2)C22—C23—C18119.69 (18)
C5—C4—H4119.4C22—C23—C24133.32 (19)
C3—C4—H4119.4C18—C23—C24106.96 (17)
C4—C5—C6119.4 (2)C25—C24—C29119.35 (19)
C4—C5—H5120.3C25—C24—C23133.94 (19)
C6—C5—H5120.3C29—C24—C23106.69 (17)
C5—C6—C1119.1 (2)C26—C25—C24119.3 (2)
C5—C6—C7134.7 (2)C26—C25—H25120.4
C1—C6—C7106.15 (17)C24—C25—H25120.4
C8—C7—C12118.8 (2)C25—C26—C27121.1 (2)
C8—C7—C6133.57 (19)C25—C26—H26119.4
C12—C7—C6107.61 (17)C27—C26—H26119.4
C9—C8—C7119.48 (19)C28—C27—C26120.8 (2)
C9—C8—H8120.3C28—C27—H27119.6
C7—C8—H8120.3C26—C27—H27119.6
C8—C9—C10120.9 (2)C27—C28—C29118.6 (2)
C8—C9—H9119.6C27—C28—H28120.7
C10—C9—H9119.6C29—C28—H28120.7
C11—C10—C9120.6 (2)C28—C29—N3130.39 (18)
C11—C10—H10119.7C28—C29—C24120.81 (18)
C9—C10—H10119.7N3—C29—C24108.77 (16)
C12—C11—C10117.93 (19)N3—C30—N4113.15 (15)
C12—C11—H11121.0N3—C30—H30A108.9
C10—C11—H11121.0N4—C30—H30A108.9
C11—C12—N1129.44 (17)N3—C30—H30B108.9
C11—C12—C7122.36 (19)N4—C30—H30B108.9
N1—C12—C7108.18 (17)H30A—C30—H30B107.8
N1—C13—N2111.93 (15)N4—C31—C32116.10 (18)
N1—C13—H13A109.2N4—C31—H31A108.3
N2—C13—H13A109.2C32—C31—H31A108.3
N1—C13—H13B109.2N4—C31—H31B108.3
N2—C13—H13B109.2C32—C31—H31B108.3
H13A—C13—H13B107.9H31A—C31—H31B107.4
N2—C14—C15113.21 (17)C31—C32—H32A109.5
N2—C14—H14A108.9C31—C32—H32B109.5
C15—C14—H14A108.9H32A—C32—H32B109.5
N2—C14—H14B108.9C31—C32—H32C109.5
C15—C14—H14B108.9H32A—C32—H32C109.5
H14A—C14—H14B107.7H32B—C32—H32C109.5
C14—C15—H15A109.5N4—C33—C34113.93 (19)
C14—C15—H15B109.5N4—C33—H33A108.8
H15A—C15—H15B109.5C34—C33—H33A108.8
C14—C15—H15C109.5N4—C33—H33B108.8
H15A—C15—H15C109.5C34—C33—H33B108.8
H15B—C15—H15C109.5H33A—C33—H33B107.7
N2—C16—C17113.83 (16)C33—C34—H34A109.5
N2—C16—H16A108.8C33—C34—H34B109.5
C17—C16—H16A108.8H34A—C34—H34B109.5
N2—C16—H16B108.8C33—C34—H34C109.5
C17—C16—H16B108.8H34A—C34—H34C109.5
H16A—C16—H16B107.7H34B—C34—H34C109.5
C16—C17—H17A109.5C1—N1—C12108.96 (15)
C16—C17—H17B109.5C1—N1—C13126.47 (17)
H17A—C17—H17B109.5C12—N1—C13124.41 (16)
C16—C17—H17C109.5C13—N2—C16109.79 (15)
H17A—C17—H17C109.5C13—N2—C14110.73 (15)
H17B—C17—H17C109.5C16—N2—C14111.71 (15)
C19—C18—N3129.58 (18)C29—N3—C18108.65 (15)
C19—C18—C23121.49 (18)C29—N3—C30127.21 (17)
N3—C18—C23108.92 (16)C18—N3—C30124.03 (16)
C20—C19—C18117.6 (2)C30—N4—C33111.05 (16)
C20—C19—H19121.2C30—N4—C31110.64 (16)
C18—C19—H19121.2C33—N4—C31114.16 (17)
N1—C1—C2—C3179.13 (19)C23—C24—C25—C26−178.5 (2)
C6—C1—C2—C31.1 (3)C24—C25—C26—C270.8 (3)
C1—C2—C3—C40.4 (3)C25—C26—C27—C28−0.7 (3)
C2—C3—C4—C5−2.0 (3)C26—C27—C28—C29−0.4 (3)
C3—C4—C5—C61.9 (3)C27—C28—C29—N3179.32 (19)
C4—C5—C6—C1−0.4 (3)C27—C28—C29—C241.5 (3)
C4—C5—C6—C7−177.7 (2)C25—C24—C29—C28−1.4 (3)
N1—C1—C6—C5−179.48 (17)C23—C24—C29—C28177.65 (17)
C2—C1—C6—C5−1.1 (3)C25—C24—C29—N3−179.67 (16)
N1—C1—C6—C7−1.5 (2)C23—C24—C29—N3−0.6 (2)
C2—C1—C6—C7176.88 (18)C2—C1—N1—C12−176.97 (19)
C5—C6—C7—C81.5 (4)C6—C1—N1—C121.2 (2)
C1—C6—C7—C8−176.0 (2)C2—C1—N1—C137.6 (3)
C5—C6—C7—C12178.7 (2)C6—C1—N1—C13−174.21 (16)
C1—C6—C7—C121.2 (2)C11—C12—N1—C1178.27 (19)
C12—C7—C8—C90.4 (3)C7—C12—N1—C1−0.5 (2)
C6—C7—C8—C9177.3 (2)C11—C12—N1—C13−6.2 (3)
C7—C8—C9—C101.0 (3)C7—C12—N1—C13175.11 (16)
C8—C9—C10—C11−1.3 (3)N2—C13—N1—C1108.6 (2)
C9—C10—C11—C120.1 (3)N2—C13—N1—C12−66.2 (2)
C10—C11—C12—N1−177.16 (18)N1—C13—N2—C16172.62 (17)
C10—C11—C12—C71.4 (3)N1—C13—N2—C14−63.6 (2)
C8—C7—C12—C11−1.6 (3)C17—C16—N2—C13−66.3 (2)
C6—C7—C12—C11−179.32 (17)C17—C16—N2—C14170.45 (18)
C8—C7—C12—N1177.19 (17)C15—C14—N2—C13167.25 (16)
C6—C7—C12—N1−0.5 (2)C15—C14—N2—C16−70.0 (2)
N3—C18—C19—C20−178.99 (19)C28—C29—N3—C18−177.64 (19)
C23—C18—C19—C200.6 (3)C24—C29—N3—C180.4 (2)
C18—C19—C20—C211.2 (3)C28—C29—N3—C30−1.4 (3)
C19—C20—C21—C22−1.6 (3)C24—C29—N3—C30176.64 (16)
C20—C21—C22—C230.2 (3)C19—C18—N3—C29179.61 (19)
C21—C22—C23—C181.5 (3)C23—C18—N3—C290.0 (2)
C21—C22—C23—C24179.0 (2)C19—C18—N3—C303.2 (3)
C19—C18—C23—C22−1.9 (3)C23—C18—N3—C30−176.41 (16)
N3—C18—C23—C22177.72 (16)N4—C30—N3—C29104.2 (2)
C19—C18—C23—C24179.99 (17)N4—C30—N3—C18−80.1 (2)
N3—C18—C23—C24−0.4 (2)N3—C30—N4—C33−75.7 (2)
C22—C23—C24—C251.7 (4)N3—C30—N4—C31156.47 (18)
C18—C23—C24—C25179.5 (2)C34—C33—N4—C30177.03 (18)
C22—C23—C24—C29−177.1 (2)C34—C33—N4—C31−57.1 (2)
C18—C23—C24—C290.6 (2)C32—C31—N4—C3069.2 (3)
C29—C24—C25—C260.2 (3)C32—C31—N4—C33−56.9 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2745).

References

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