Bis(9-ethyl­carbazol-3-yl)ethane

In the title compound, C₃₀H₂₈N₂, each carbazole skeleton is essentially planar. The planes of the two carbazole ring systems are nearly parallel, with a dihedral angle of 2.33 (19)°. The crystal packing is stabilized only by van der Waals forces and weak C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.056
• wR factor = 0.132
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.66
PLAT128_ALERT_4_C Non-standard setting of Space group Pna21   ....    P21cn
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
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
              C30 H28 N2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.06
           From the CIF: _reflns_number_total               2214
           Count of symmetry unique reflns         2216
           Completeness (_total/calc)             99.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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).

Bis(9-ethyl-9H-carbazol-3-yl)ethane

Crystal data

C30H28N2	F(000) = 888
Mr = 416.54	Dx = 1.196 Mg m^−3
Orthorhombic, P21cn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2n 2a	Cell parameters from 25 reflections
a = 8.1412 (5) Å	θ = 1.7–25.1°
b = 17.2919 (19) Å	µ = 0.07 mm^−1
c = 16.434 (2) Å	T = 295 K
V = 2313.5 (4) Å^3	Cube, colorless
Z = 4	0.50 × 0.50 × 0.50 mm

Data collection

Nonius CAD-4 diffractometer	Rint = 0
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 1.7°
Graphite monochromator	h = 0→9
ω scans	k = 0→20
2214 measured reflections	l = 0→19
2214 independent reflections	3 standard reflections every 120 min
1136 reflections with I > 2σ(I)	intensity decay: 0.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
2214 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.13 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

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)

- 7.0661 (0.0062) x + 1.3537 (0.0138) y - 8.0602 (0.0220) z = 1.3502 (0.0073)

* -0.0347 (0.0057) C1 * -0.0662 (0.0055) C2 * -0.0309 (0.0049) C3 * 0.0435 (0.0046) C4 * 0.0568 (0.0057) C4A * 0.0642 (0.0059) C4B * -0.0045 (0.0049) C5 * -0.0525 (0.0057) C6 * -0.0583 (0.0059) C7 * -0.0003 (0.0053) C8 * 0.0458 (0.0051) C8A * 0.0174 (0.0051) C9A * 0.0197 (0.0046) N

Rms deviation of fitted atoms = 0.0436

7.0383 (0.0065) x - 0.6759 (0.0142) y + 8.2345 (0.0228) z = 0.8978 (0.0107)

Angle to previous plane (with approximate e.s.d.) = 2.33 (0.19)

* 0.0044 (0.0051) C1' * -0.0671 (0.0054) C2' * -0.0635 (0.0049) C3' * 0.0235 (0.0049) C4' * 0.0679 (0.0055) C4A' * 0.0523 (0.0058) C4B' * 0.0215 (0.0053) C5' * -0.0317 (0.0064) C6' * -0.0481 (0.0070) C7' * -0.0412 (0.0062) C8' * 0.0186 (0.0051) C8A' * 0.0468 (0.0051) C9A' * 0.0165 (0.0044) N'

Rms deviation of fitted atoms = 0.0436

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 (Ų)

	x	y	z	Uiso*/Ueq
N	0.2388 (6)	0.2407 (3)	−0.3389 (2)	0.0571 (13)
C1	0.2488 (9)	0.3832 (3)	−0.3170 (3)	0.0674 (17)
H1	0.3068	0.3946	−0.3642	0.081*
C2	0.2033 (9)	0.4400 (3)	−0.2636 (3)	0.0725 (19)
H2	0.2334	0.4907	−0.2756	0.087*
C3	0.1144 (8)	0.4267 (3)	−0.1923 (3)	0.0610 (16)
C4	0.0700 (7)	0.3515 (3)	−0.1752 (3)	0.0558 (16)
H4	0.009	0.3406	−0.1288	0.067*
C4A	0.1162 (8)	0.2917 (3)	−0.2274 (3)	0.0446 (14)
C4B	0.0964 (8)	0.2097 (3)	−0.2248 (3)	0.0450 (14)
C5	0.0314 (7)	0.1574 (3)	−0.1680 (3)	0.0588 (16)
H5	−0.0174	0.1756	−0.1206	0.071*
C6	0.0397 (9)	0.0795 (4)	−0.1825 (4)	0.076 (2)
H6	−0.0052	0.0449	−0.1453	0.091*
C7	0.1159 (10)	0.0519 (3)	−0.2532 (4)	0.077 (2)
H7	0.1221	−0.0011	−0.262	0.092*
C8	0.1817 (8)	0.1015 (4)	−0.3097 (4)	0.0691 (19)
H8	0.2308	0.0827	−0.3569	0.083*
C8A	0.1730 (7)	0.1798 (3)	−0.2947 (3)	0.0512 (16)
C9A	0.2060 (7)	0.3092 (3)	−0.2983 (3)	0.0483 (14)
N'	0.1002 (6)	0.7865 (3)	0.0899 (2)	0.0603 (14)
C1'	0.0862 (7)	0.6429 (3)	0.0886 (3)	0.0613 (16)
H1'	0.0308	0.6379	0.1378	0.074*
C2'	0.1247 (8)	0.5791 (3)	0.0418 (3)	0.0677 (18)
H2'	0.0913	0.5306	0.06	0.081*
C3'	0.2118 (8)	0.5838 (3)	−0.0318 (3)	0.0606 (17)
C4'	0.2625 (7)	0.6557 (3)	−0.0586 (3)	0.0529 (15)
H4'	0.3229	0.6604	−0.1064	0.064*
C4A'	0.2224 (7)	0.7209 (3)	−0.0136 (3)	0.0448 (14)
C4B'	0.2442 (8)	0.8024 (3)	−0.0275 (3)	0.0469 (14)
C5'	0.3149 (8)	0.8472 (4)	−0.0880 (3)	0.0669 (17)
H5'	0.3663	0.8236	−0.132	0.08*
C6'	0.3094 (11)	0.9267 (4)	−0.0832 (4)	0.091 (2)
H6'	0.3566	0.9564	−0.1242	0.109*
C7'	0.2357 (11)	0.9619 (3)	−0.0193 (4)	0.092 (2)
H7'	0.236	1.0156	−0.0172	0.111*
C8'	0.1603 (10)	0.9216 (4)	0.0427 (4)	0.077 (2)
H8'	0.108	0.947	0.0853	0.093*
C8A'	0.1661 (7)	0.8415 (4)	0.0384 (3)	0.0551 (15)
C9A'	0.1334 (8)	0.7143 (3)	0.0593 (3)	0.0507 (15)
C10	0.3213 (8)	0.2360 (4)	−0.4171 (3)	0.0706 (18)
H10A	0.3765	0.1864	−0.4213	0.085*
H10B	0.4042	0.2762	−0.4202	0.085*
C11	0.2044 (10)	0.2448 (5)	−0.4876 (3)	0.113 (3)
H11A	0.2641	0.2404	−0.5378	0.17*
H11B	0.1524	0.2945	−0.4849	0.17*
H11C	0.1224	0.205	−0.4851	0.17*
C10'	0.0117 (9)	0.8010 (4)	0.1660 (3)	0.0781 (19)
H10C	−0.0753	0.7631	0.1719	0.094*
H10D	−0.0387	0.8518	0.1636	0.094*
C11'	0.1230 (10)	0.7970 (4)	0.2386 (3)	0.102 (3)
H11D	0.0607	0.8069	0.2871	0.153*
H11E	0.2082	0.8351	0.2334	0.153*
H11F	0.1714	0.7465	0.2418	0.153*
C12	0.0805 (8)	0.4923 (3)	−0.1337 (3)	0.0686 (17)
H12A	−0.0074	0.4775	−0.0971	0.082*
H12B	0.0447	0.5374	−0.164	0.082*
C12'	0.2339 (8)	0.5129 (3)	−0.0840 (3)	0.0685 (17)
H12C	0.262	0.4694	−0.0494	0.082*
H12D	0.325	0.5214	−0.121	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.052 (3)	0.075 (3)	0.045 (2)	0.001 (3)	0.006 (3)	−0.009 (2)
C1	0.078 (5)	0.075 (4)	0.050 (3)	−0.008 (4)	0.018 (4)	0.006 (3)
C2	0.079 (5)	0.067 (4)	0.071 (4)	−0.006 (4)	−0.006 (4)	0.020 (3)
C3	0.065 (5)	0.061 (4)	0.057 (3)	0.002 (3)	−0.010 (4)	0.004 (3)
C4	0.055 (4)	0.066 (4)	0.046 (3)	0.001 (3)	−0.003 (3)	0.006 (3)
C4A	0.040 (4)	0.052 (3)	0.041 (3)	0.002 (3)	−0.002 (3)	0.005 (3)
C4B	0.039 (4)	0.058 (3)	0.038 (3)	0.001 (3)	−0.005 (3)	−0.001 (3)
C5	0.055 (4)	0.073 (4)	0.049 (3)	−0.009 (4)	−0.007 (3)	0.000 (3)
C6	0.081 (5)	0.069 (5)	0.078 (5)	−0.019 (4)	−0.013 (4)	0.006 (4)
C7	0.080 (5)	0.058 (4)	0.093 (5)	−0.005 (4)	−0.017 (5)	−0.012 (4)
C8	0.060 (5)	0.080 (4)	0.067 (4)	0.001 (4)	−0.006 (4)	−0.024 (3)
C8A	0.042 (4)	0.064 (4)	0.047 (3)	−0.001 (3)	−0.010 (3)	−0.008 (3)
C9A	0.039 (4)	0.061 (4)	0.045 (3)	−0.007 (3)	0.004 (3)	0.004 (3)
N'	0.063 (4)	0.073 (3)	0.045 (2)	−0.001 (3)	0.004 (3)	−0.018 (3)
C1'	0.050 (4)	0.087 (5)	0.047 (3)	0.002 (4)	0.007 (3)	0.004 (3)
C2'	0.060 (5)	0.072 (4)	0.071 (4)	0.000 (4)	0.007 (4)	0.022 (3)
C3'	0.058 (5)	0.057 (4)	0.067 (4)	0.014 (3)	−0.005 (4)	0.001 (3)
C4'	0.046 (4)	0.065 (4)	0.048 (3)	0.007 (3)	−0.001 (3)	−0.007 (3)
C4A'	0.029 (4)	0.062 (4)	0.043 (3)	0.001 (3)	−0.008 (3)	0.006 (2)
C4B'	0.034 (3)	0.062 (3)	0.045 (3)	0.002 (3)	−0.001 (3)	−0.003 (3)
C5'	0.072 (5)	0.065 (4)	0.064 (4)	−0.011 (4)	−0.001 (4)	0.004 (3)
C6'	0.118 (7)	0.073 (5)	0.082 (5)	−0.019 (5)	−0.007 (5)	0.010 (4)
C7'	0.114 (7)	0.062 (4)	0.100 (5)	−0.006 (5)	−0.011 (6)	0.002 (4)
C8'	0.082 (6)	0.068 (4)	0.082 (5)	0.000 (4)	−0.008 (4)	−0.021 (4)
C8A'	0.041 (4)	0.071 (4)	0.054 (3)	−0.002 (4)	−0.011 (3)	−0.002 (3)
C9A'	0.043 (4)	0.065 (4)	0.044 (3)	−0.004 (3)	−0.009 (3)	0.004 (3)
C10	0.051 (4)	0.115 (5)	0.045 (3)	0.009 (4)	0.009 (3)	−0.012 (3)
C11	0.072 (6)	0.228 (8)	0.040 (3)	0.030 (6)	−0.001 (4)	−0.002 (4)
C10'	0.068 (5)	0.111 (5)	0.055 (4)	−0.003 (4)	0.017 (4)	−0.024 (4)
C11'	0.077 (6)	0.180 (7)	0.049 (3)	−0.028 (6)	0.016 (4)	−0.020 (4)
C12	0.057 (4)	0.060 (4)	0.089 (4)	0.008 (3)	−0.004 (4)	−0.008 (3)
C12'	0.061 (4)	0.062 (4)	0.082 (4)	0.018 (3)	0.002 (4)	0.002 (3)

Geometric parameters (Å, º)

N—C9A	1.385 (6)	C3'—C12'	1.508 (7)
N—C8A	1.387 (6)	C4'—C4A'	1.386 (7)
N—C10	1.453 (6)	C4'—H4'	0.93
C1—C9A	1.361 (7)	C4A'—C9A'	1.406 (7)
C1—C2	1.369 (7)	C4A'—C4B'	1.439 (7)
C1—H1	0.93	C4B'—C5'	1.386 (7)
C2—C3	1.397 (8)	C4B'—C8A'	1.426 (7)
C2—H2	0.93	C5'—C6'	1.377 (7)
C3—C4	1.378 (6)	C5'—H5'	0.93
C3—C12	1.513 (7)	C6'—C7'	1.354 (9)
C4—C4A	1.395 (6)	C6'—H6'	0.93
C4—H4	0.93	C7'—C8'	1.377 (8)
C4A—C9A	1.408 (7)	C7'—H7'	0.93
C4A—C4B	1.427 (6)	C8'—C8A'	1.389 (7)
C4B—C5	1.403 (7)	C8'—H8'	0.93
C4B—C8A	1.406 (7)	C10—C11	1.507 (8)
C5—C6	1.369 (7)	C10—H10A	0.97
C5—H5	0.93	C10—H10B	0.97
C6—C7	1.402 (8)	C11—H11A	0.96
C6—H6	0.93	C11—H11B	0.96
C7—C8	1.372 (8)	C11—H11C	0.96
C7—H7	0.93	C10'—C11'	1.501 (8)
C8—C8A	1.379 (7)	C10'—H10C	0.97
C8—H8	0.93	C10'—H10D	0.97
N'—C9A'	1.373 (6)	C11'—H11D	0.96
N'—C8A'	1.382 (7)	C11'—H11E	0.96
N'—C10'	1.464 (7)	C11'—H11F	0.96
C1'—C9A'	1.380 (7)	C12—C12'	1.534 (7)
C1'—C2'	1.380 (7)	C12—H12A	0.97
C1'—H1'	0.93	C12—H12B	0.97
C2'—C3'	1.405 (7)	C12'—H12C	0.97
C2'—H2'	0.93	C12'—H12D	0.97
C3'—C4'	1.384 (7)
C9A—N—C8A	108.8 (4)	C5'—C4B'—C8A'	117.7 (5)
C9A—N—C10	124.3 (5)	C5'—C4B'—C4A'	135.5 (5)
C8A—N—C10	126.8 (5)	C8A'—C4B'—C4A'	106.8 (5)
C9A—C1—C2	117.4 (5)	C6'—C5'—C4B'	120.3 (6)
C9A—C1—H1	121.3	C6'—C5'—H5'	119.9
C2—C1—H1	121.3	C4B'—C5'—H5'	119.9
C1—C2—C3	124.0 (5)	C7'—C6'—C5'	120.5 (6)
C1—C2—H2	118	C7'—C6'—H6'	119.8
C3—C2—H2	118	C5'—C6'—H6'	119.8
C4—C3—C2	117.6 (5)	C6'—C7'—C8'	122.9 (6)
C4—C3—C12	122.0 (5)	C6'—C7'—H7'	118.5
C2—C3—C12	120.3 (5)	C8'—C7'—H7'	118.5
C3—C4—C4A	120.2 (5)	C7'—C8'—C8A'	116.8 (6)
C3—C4—H4	119.9	C7'—C8'—H8'	121.6
C4A—C4—H4	119.9	C8A'—C8'—H8'	121.6
C4—C4A—C9A	119.3 (5)	N'—C8A'—C8'	129.9 (6)
C4—C4A—C4B	133.4 (5)	N'—C8A'—C4B'	108.2 (5)
C9A—C4A—C4B	107.3 (4)	C8'—C8A'—C4B'	121.8 (6)
C5—C4B—C8A	118.2 (5)	N'—C9A'—C1'	129.2 (5)
C5—C4B—C4A	134.7 (5)	N'—C9A'—C4A'	109.9 (5)
C8A—C4B—C4A	106.9 (4)	C1'—C9A'—C4A'	120.9 (5)
C6—C5—C4B	120.1 (5)	N—C10—C11	112.5 (5)
C6—C5—H5	120	N—C10—H10A	109.1
C4B—C5—H5	120	C11—C10—H10A	109.1
C5—C6—C7	120.0 (6)	N—C10—H10B	109.1
C5—C6—H6	120	C11—C10—H10B	109.1
C7—C6—H6	120	H10A—C10—H10B	107.8
C8—C7—C6	121.4 (6)	C10—C11—H11A	109.5
C8—C7—H7	119.3	C10—C11—H11B	109.5
C6—C7—H7	119.3	H11A—C11—H11B	109.5
C7—C8—C8A	118.2 (5)	C10—C11—H11C	109.5
C7—C8—H8	120.9	H11A—C11—H11C	109.5
C8A—C8—H8	120.9	H11B—C11—H11C	109.5
C8—C8A—N	129.2 (5)	N'—C10'—C11'	112.0 (6)
C8—C8A—C4B	122.1 (5)	N'—C10'—H10C	109.2
N—C8A—C4B	108.7 (4)	C11'—C10'—H10C	109.2
C1—C9A—N	130.2 (5)	N'—C10'—H10D	109.2
C1—C9A—C4A	121.5 (5)	C11'—C10'—H10D	109.2
N—C9A—C4A	108.3 (4)	H10C—C10'—H10D	107.9
C9A'—N'—C8A'	109.0 (4)	C10'—C11'—H11D	109.5
C9A'—N'—C10'	124.4 (5)	C10'—C11'—H11E	109.5
C8A'—N'—C10'	126.6 (5)	H11D—C11'—H11E	109.5
C9A'—C1'—C2'	117.2 (5)	C10'—C11'—H11F	109.5
C9A'—C1'—H1'	121.4	H11D—C11'—H11F	109.5
C2'—C1'—H1'	121.4	H11E—C11'—H11F	109.5
C1'—C2'—C3'	123.2 (5)	C3—C12—C12'	111.4 (5)
C1'—C2'—H2'	118.4	C3—C12—H12A	109.4
C3'—C2'—H2'	118.4	C12'—C12—H12A	109.4
C4'—C3'—C2'	118.5 (5)	C3—C12—H12B	109.4
C4'—C3'—C12'	120.9 (5)	C12'—C12—H12B	109.4
C2'—C3'—C12'	120.3 (5)	H12A—C12—H12B	108
C3'—C4'—C4A'	119.4 (5)	C3'—C12'—C12	113.3 (5)
C3'—C4'—H4'	120.3	C3'—C12'—H12C	108.9
C4A'—C4'—H4'	120.3	C12—C12'—H12C	108.9
C4'—C4A'—C9A'	120.7 (5)	C3'—C12'—H12D	108.9
C4'—C4A'—C4B'	133.0 (5)	C12—C12'—H12D	108.9
C9A'—C4A'—C4B'	106.2 (5)	H12C—C12'—H12D	107.7
C9A—C1—C2—C3	−0.8 (10)	C3'—C4'—C4A'—C9A'	1.0 (8)
C1—C2—C3—C4	−0.2 (9)	C3'—C4'—C4A'—C4B'	−174.3 (6)
C1—C2—C3—C12	175.4 (6)	C4'—C4A'—C4B'—C5'	−1.9 (11)
C2—C3—C4—C4A	1.2 (8)	C9A'—C4A'—C4B'—C5'	−177.7 (7)
C12—C3—C4—C4A	−174.3 (6)	C4'—C4A'—C4B'—C8A'	175.7 (6)
C3—C4—C4A—C9A	−1.1 (8)	C9A'—C4A'—C4B'—C8A'	−0.1 (6)
C3—C4—C4A—C4B	176.6 (6)	C8A'—C4B'—C5'—C6'	0.4 (9)
C4—C4A—C4B—C5	−3.8 (11)	C4A'—C4B'—C5'—C6'	177.8 (7)
C9A—C4A—C4B—C5	174.2 (7)	C4B'—C5'—C6'—C7'	0.3 (11)
C4—C4A—C4B—C8A	−178.6 (6)	C5'—C6'—C7'—C8'	−1.4 (13)
C9A—C4A—C4B—C8A	−0.7 (6)	C6'—C7'—C8'—C8A'	1.6 (12)
C8A—C4B—C5—C6	−1.7 (9)	C9A'—N'—C8A'—C8'	178.1 (6)
C4A—C4B—C5—C6	−176.1 (6)	C10'—N'—C8A'—C8'	−3.0 (10)
C4B—C5—C6—C7	1.2 (10)	C9A'—N'—C8A'—C4B'	0.0 (6)
C5—C6—C7—C8	−0.8 (11)	C10'—N'—C8A'—C4B'	178.9 (5)
C6—C7—C8—C8A	0.9 (10)	C7'—C8'—C8A'—N'	−178.7 (7)
C7—C8—C8A—N	175.3 (6)	C7'—C8'—C8A'—C4B'	−0.9 (10)
C7—C8—C8A—C4B	−1.4 (9)	C5'—C4B'—C8A'—N'	178.2 (5)
C9A—N—C8A—C8	−176.9 (6)	C4A'—C4B'—C8A'—N'	0.1 (6)
C10—N—C8A—C8	6.2 (9)	C5'—C4B'—C8A'—C8'	−0.1 (9)
C9A—N—C8A—C4B	0.2 (6)	C4A'—C4B'—C8A'—C8'	−178.2 (5)
C10—N—C8A—C4B	−176.7 (5)	C8A'—N'—C9A'—C1'	−177.2 (6)
C5—C4B—C8A—C8	1.8 (9)	C10'—N'—C9A'—C1'	3.8 (9)
C4A—C4B—C8A—C8	177.7 (5)	C8A'—N'—C9A'—C4A'	−0.1 (6)
C5—C4B—C8A—N	−175.5 (5)	C10'—N'—C9A'—C4A'	−179.0 (6)
C4A—C4B—C8A—N	0.3 (6)	C2'—C1'—C9A'—N'	174.5 (6)
C2—C1—C9A—N	−177.9 (6)	C2'—C1'—C9A'—C4A'	−2.4 (8)
C2—C1—C9A—C4A	0.9 (9)	C4'—C4A'—C9A'—N'	−176.3 (5)
C8A—N—C9A—C1	178.3 (6)	C4B'—C4A'—C9A'—N'	0.1 (6)
C10—N—C9A—C1	−4.7 (9)	C4'—C4A'—C9A'—C1'	1.1 (8)
C8A—N—C9A—C4A	−0.6 (6)	C4B'—C4A'—C9A'—C1'	177.6 (5)
C10—N—C9A—C4A	176.4 (5)	C9A—N—C10—C11	−86.0 (7)
C4—C4A—C9A—C1	0.1 (9)	C8A—N—C10—C11	90.5 (7)
C4B—C4A—C9A—C1	−178.2 (5)	C9A'—N'—C10'—C11'	83.9 (7)
C4—C4A—C9A—N	179.1 (5)	C8A'—N'—C10'—C11'	−94.8 (7)
C4B—C4A—C9A—N	0.8 (6)	C4—C3—C12—C12'	99.5 (7)
C9A'—C1'—C2'—C3'	1.7 (9)	C2—C3—C12—C12'	−75.8 (7)
C1'—C2'—C3'—C4'	0.4 (9)	C4'—C3'—C12'—C12	−95.7 (7)
C1'—C2'—C3'—C12'	−173.5 (6)	C2'—C3'—C12'—C12	78.0 (7)
C2'—C3'—C4'—C4A'	−1.7 (8)	C3—C12—C12'—C3'	173.4 (5)
C12'—C3'—C4'—C4A'	172.1 (5)