9-Methyl­ene-10,10-bis­(phenyl­ethyn­yl)fluorene–tetra­cyano-para-quinodimethane (2/3)

Jones, P.G.; Bubenitschek, P.; Hopf, H.; Berger, H.

doi:10.1107/S1600536805007142

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9-Methylene-10,10-bis(phenylethynyl)fluorene–tetracyano-para-quinodimethane (2/3)

P. G. Jones, P. Bubenitschek, H. Hopf and H. Berger

In the title compound, 2C₃₀H₁₈·3C₁₂H₄N₄, the asymmetric unit consists of half a formula unit (one quinodimethane molecule displays inversion symmetry). There is no ring stacking; instead, the residues associate by weak C—H

N contacts in planes parallel to (2 $\overline{1}$ $\overline{1}$ ).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007142/bt6618sup1.cif Contains datablocks 3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007142/bt66183sup2.hkl Contains datablock 3

CCDC reference: 270239

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.048
wR factor = 0.157
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11'   ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12    -   C13    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12'   -   C13'   ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C19    -   C20    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C20    -   C21    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C28    -   C29    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C29    -   C30    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C31    -   C32    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C32    -   C33    ...       1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  N3      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  N5      ..       2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  N6      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  N4      ..       2.78 Ang.

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

9-Methylene-10,10-bis(phenylethynyl)fluorene–tetracyano-para-quinodimethane (2/3) top

Crystal data top

2C₃₀H₁₈·3C₁₂H₄N₄	Z = 1
M_r = 1369.46	F(000) = 708
Triclinic, P1	D_x = 1.290 Mg m⁻³
a = 9.589 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.617 (5) Å	Cell parameters from 25 reflections
c = 21.952 (12) Å	θ = 10–11.5°
α = 80.81 (3)°	µ = 0.08 mm⁻¹
β = 80.64 (4)°	T = 173 K
γ = 62.50 (4)°	Plate, dark blue–violet
V = 1763.4 (16) Å³	0.7 × 0.7 × 0.1 mm

Data collection top

Siemens R3 diffractometer	R_int = 0.050
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.2°
Graphite monochromator	h = −11→9
ω scans	k = −11→9
9928 measured reflections	l = −26→26
6211 independent reflections	3 standard reflections every 147 reflections
2764 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0588P)²] where P = (F_o² + 2F_c²)/3
6211 reflections	(Δ/σ)_max < 0.001
487 parameters	Δρ_max = 0.22 e Å⁻³
461 restraints	Δρ_min = −0.25 e Å⁻³

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.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.2208 (0.0102) x + 3.0831 (0.0116) y + 5.6276 (0.0269) z = 3.8141 (0.0269)

* -0.0047 (0.0021) C13 * 0.0018 (0.0022) C14 * 0.0030 (0.0023) C15 * -0.0050 (0.0024) C16 * 0.0021 (0.0023) C17 * 0.0028 (0.0022) C18

Rms deviation of fitted atoms = 0.0034

- 6.3838 (0.0057) x + 3.0427 (0.0042) y + 4.4737 (0.0158) z = 2.4542 (0.0105)

Angle to previous plane (with approximate e.s.d.) = 3.10 (0.18)

* -0.0319 (0.0025) C1 * -0.0407 (0.0026) C2 * -0.0036 (0.0026) C3 * 0.0207 (0.0026) C4 * 0.0158 (0.0024) C5 * -0.0176 (0.0025) C6 * -0.0372 (0.0026) C7 * -0.0178 (0.0025) C8 * 0.0517 (0.0023) C9 * 0.0091 (0.0026) C1A * 0.0205 (0.0026) C4A * 0.0189 (0.0026) C5A * 0.0121 (0.0025) C8A

Rms deviation of fitted atoms = 0.0264

- 3.6952 (0.0135) x + 5.8249 (0.0120) y + 6.2196 (0.0297) z = 4.4691 (0.0290)

Angle to previous plane (with approximate e.s.d.) = 19.21 (0.17)

* 0.0075 (0.0023) C13' * -0.0118 (0.0025) C14' * 0.0059 (0.0027) C15' * 0.0043 (0.0030) C16' * -0.0086 (0.0028) C17' * 0.0027 (0.0024) C18'

Rms deviation of fitted atoms = 0.0074

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0693 (3)	−0.1150 (4)	0.71856 (14)	0.0414 (8)
H1	0.0850	−0.1514	0.7609	0.050*
C1A	0.1018 (3)	0.0082 (3)	0.69025 (13)	0.0338 (7)
C2	0.0134 (4)	−0.1843 (4)	0.68398 (15)	0.0478 (9)
H2	−0.0086	−0.2690	0.7030	0.057*
C3	−0.0110 (4)	−0.1320 (4)	0.62183 (16)	0.0513 (9)
H3	−0.0509	−0.1794	0.5990	0.062*
C4	0.0234 (4)	−0.0102 (4)	0.59356 (14)	0.0437 (8)
H4	0.0081	0.0256	0.5511	0.052*
C4A	0.0802 (3)	0.0590 (3)	0.62750 (13)	0.0348 (7)
C5	0.1291 (3)	0.2716 (4)	0.55156 (13)	0.0404 (8)
H5	0.0933	0.2541	0.5170	0.048*
C5A	0.1273 (3)	0.1850 (3)	0.60861 (13)	0.0326 (7)
C6	0.1841 (4)	0.3842 (4)	0.54607 (14)	0.0443 (8)
H6	0.1868	0.4437	0.5073	0.053*
C7	0.2349 (4)	0.4100 (4)	0.59666 (14)	0.0466 (9)
H7	0.2727	0.4870	0.5921	0.056*
C8	0.2320 (4)	0.3263 (4)	0.65379 (14)	0.0433 (8)
H8	0.2667	0.3462	0.6881	0.052*
C8A	0.1782 (3)	0.2133 (3)	0.66048 (12)	0.0344 (7)
C9	0.1583 (3)	0.1061 (3)	0.71379 (12)	0.0339 (7)
C10	0.1817 (3)	0.1050 (3)	0.77377 (13)	0.0364 (8)
C11	0.2335 (3)	0.2073 (4)	0.79404 (13)	0.0378 (8)
C12	0.2768 (4)	0.2846 (4)	0.81691 (13)	0.0388 (8)
C13	0.3345 (3)	0.3744 (4)	0.84159 (13)	0.0376 (8)
C14	0.3598 (4)	0.4950 (4)	0.80468 (15)	0.0462 (8)
H14	0.3341	0.5202	0.7630	0.055*
C15	0.4215 (4)	0.5778 (4)	0.82762 (17)	0.0535 (9)
H15	0.4380	0.6597	0.8022	0.064*
C16	0.4589 (4)	0.5400 (4)	0.88830 (18)	0.0606 (10)
H16	0.5027	0.5956	0.9044	0.073*
C17	0.4335 (4)	0.4231 (4)	0.92557 (16)	0.0552 (10)
H17	0.4589	0.3996	0.9672	0.066*
C18	0.3716 (4)	0.3392 (4)	0.90319 (14)	0.0482 (9)
H18	0.3543	0.2586	0.9292	0.058*
C11'	0.1539 (4)	0.0028 (4)	0.82435 (14)	0.0415 (8)
C12'	0.1306 (4)	−0.0710 (4)	0.87059 (14)	0.0435 (8)
C13'	0.0991 (4)	−0.1572 (4)	0.92590 (13)	0.0436 (8)
C14'	−0.0008 (4)	−0.2258 (4)	0.92764 (15)	0.0573 (10)
H14'	−0.0458	−0.2198	0.8913	0.069*
C15'	−0.0350 (5)	−0.3029 (5)	0.98236 (18)	0.0743 (12)
H15'	−0.1061	−0.3471	0.9837	0.089*
C16'	0.0334 (5)	−0.3160 (5)	1.03499 (18)	0.0804 (14)
H16'	0.0102	−0.3694	1.0725	0.096*
C17'	0.1353 (5)	−0.2509 (5)	1.03254 (16)	0.0786 (13)
H17'	0.1839	−0.2615	1.0686	0.094*
C18'	0.1686 (4)	−0.1707 (4)	0.97900 (14)	0.0596 (10)
H18'	0.2381	−0.1250	0.9782	0.071*
C19	0.3879 (4)	1.0804 (4)	0.14087 (15)	0.0469 (9)
C20	0.3729 (3)	1.0196 (4)	0.20428 (13)	0.0389 (8)
C21	0.4173 (4)	1.0841 (4)	0.24802 (14)	0.0402 (8)
C22	0.3222 (3)	0.9047 (3)	0.22244 (13)	0.0354 (7)
C23	0.2690 (3)	0.8468 (4)	0.17949 (13)	0.0374 (8)
H23	0.2648	0.8905	0.1374	0.045*
C24	0.2250 (3)	0.7320 (3)	0.19777 (13)	0.0375 (8)
H24	0.1883	0.6972	0.1684	0.045*
C25	0.2318 (3)	0.6594 (3)	0.26086 (13)	0.0350 (7)
C26	0.2810 (3)	0.7199 (4)	0.30435 (13)	0.0385 (8)
H26	0.2833	0.6773	0.3465	0.046*
C27	0.3239 (3)	0.8361 (4)	0.28627 (13)	0.0370 (8)
H27	0.3561	0.8742	0.3160	0.044*
C28	0.1929 (4)	0.4610 (4)	0.33948 (15)	0.0416 (8)
C29	0.1930 (3)	0.5366 (4)	0.27746 (13)	0.0375 (8)
C30	0.1505 (4)	0.4739 (4)	0.23216 (14)	0.0422 (8)
N1	0.4043 (4)	1.1277 (4)	0.09029 (13)	0.0679 (9)
N2	0.4512 (3)	1.1363 (3)	0.28354 (12)	0.0527 (8)
N3	0.1919 (3)	0.3985 (3)	0.38818 (12)	0.0513 (8)
N4	0.1185 (3)	0.4205 (3)	0.19628 (13)	0.0575 (8)
C31	0.3562 (4)	0.6999 (4)	0.49761 (14)	0.0408 (8)
C32	0.4116 (3)	0.7586 (3)	0.53950 (12)	0.0341 (7)
C33	0.4208 (3)	0.6846 (3)	0.60195 (14)	0.0371 (8)
C34	0.4448 (3)	0.9498 (3)	0.45696 (12)	0.0342 (7)
H34	0.4065	0.9148	0.4283	0.041*
C35	0.4540 (3)	0.8781 (3)	0.52011 (12)	0.0332 (7)
C36	0.5112 (3)	0.9358 (3)	0.56225 (13)	0.0365 (8)
H36	0.5177	0.8920	0.6043	0.044*
N5	0.3110 (4)	0.6549 (3)	0.46327 (12)	0.0583 (8)
N6	0.4282 (3)	0.6228 (3)	0.65118 (12)	0.0489 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0380 (19)	0.043 (2)	0.0383 (17)	−0.0156 (16)	−0.0007 (14)	−0.0011 (15)
C1A	0.0283 (17)	0.0334 (18)	0.0383 (17)	−0.0124 (14)	−0.0039 (13)	−0.0038 (14)
C2	0.050 (2)	0.041 (2)	0.057 (2)	−0.0270 (17)	0.0045 (17)	−0.0062 (17)
C3	0.051 (2)	0.052 (2)	0.058 (2)	−0.0255 (19)	−0.0007 (17)	−0.0194 (18)
C4	0.045 (2)	0.049 (2)	0.0370 (17)	−0.0199 (17)	−0.0019 (15)	−0.0087 (15)
C4A	0.0319 (18)	0.0347 (18)	0.0351 (17)	−0.0129 (15)	0.0005 (13)	−0.0059 (14)
C5	0.0376 (19)	0.046 (2)	0.0300 (17)	−0.0124 (16)	−0.0050 (14)	−0.0032 (15)
C5A	0.0279 (17)	0.0324 (18)	0.0337 (16)	−0.0118 (14)	0.0012 (13)	−0.0028 (13)
C6	0.047 (2)	0.044 (2)	0.0369 (18)	−0.0209 (17)	0.0023 (15)	0.0041 (15)
C7	0.055 (2)	0.053 (2)	0.0401 (19)	−0.0340 (18)	0.0031 (16)	−0.0012 (16)
C8	0.046 (2)	0.050 (2)	0.0383 (18)	−0.0257 (17)	−0.0018 (15)	−0.0028 (15)
C8A	0.0306 (17)	0.0382 (19)	0.0308 (16)	−0.0132 (15)	−0.0004 (13)	−0.0028 (14)
C9	0.0273 (17)	0.0359 (18)	0.0342 (16)	−0.0114 (14)	−0.0023 (13)	−0.0010 (13)
C10	0.0324 (18)	0.0377 (19)	0.0349 (17)	−0.0135 (15)	−0.0026 (13)	0.0004 (14)
C11	0.0339 (19)	0.042 (2)	0.0318 (17)	−0.0139 (15)	−0.0025 (13)	−0.0005 (14)
C12	0.0367 (19)	0.042 (2)	0.0333 (17)	−0.0148 (16)	−0.0010 (14)	−0.0036 (15)
C13	0.0347 (18)	0.0397 (19)	0.0364 (17)	−0.0146 (15)	−0.0014 (14)	−0.0070 (14)
C14	0.044 (2)	0.041 (2)	0.0438 (19)	−0.0130 (16)	0.0022 (15)	−0.0045 (16)
C15	0.047 (2)	0.036 (2)	0.071 (2)	−0.0164 (17)	0.0073 (18)	−0.0099 (18)
C16	0.049 (2)	0.061 (3)	0.078 (3)	−0.026 (2)	0.002 (2)	−0.028 (2)
C17	0.053 (2)	0.068 (3)	0.044 (2)	−0.022 (2)	−0.0019 (17)	−0.0224 (18)
C18	0.049 (2)	0.055 (2)	0.0388 (19)	−0.0229 (18)	0.0046 (16)	−0.0121 (17)
C11'	0.0407 (19)	0.040 (2)	0.0372 (17)	−0.0131 (16)	−0.0058 (14)	0.0011 (15)
C12'	0.042 (2)	0.043 (2)	0.0395 (18)	−0.0147 (16)	−0.0062 (15)	0.0002 (15)
C13'	0.048 (2)	0.037 (2)	0.0332 (17)	−0.0108 (16)	−0.0005 (15)	0.0002 (14)
C14'	0.054 (2)	0.059 (2)	0.051 (2)	−0.024 (2)	−0.0067 (17)	0.0132 (18)
C15'	0.067 (3)	0.078 (3)	0.074 (3)	−0.040 (2)	0.005 (2)	0.017 (2)
C16'	0.096 (4)	0.076 (3)	0.046 (2)	−0.031 (3)	0.013 (2)	0.012 (2)
C17'	0.110 (4)	0.083 (3)	0.031 (2)	−0.037 (3)	−0.003 (2)	0.000 (2)
C18'	0.077 (3)	0.059 (2)	0.0368 (19)	−0.026 (2)	−0.0065 (18)	−0.0032 (17)
C19	0.045 (2)	0.049 (2)	0.047 (2)	−0.0212 (17)	−0.0043 (16)	−0.0020 (17)
C20	0.040 (2)	0.039 (2)	0.0352 (17)	−0.0144 (16)	−0.0035 (14)	−0.0058 (14)
C21	0.0366 (19)	0.039 (2)	0.0405 (18)	−0.0146 (16)	−0.0008 (15)	−0.0040 (15)
C22	0.0303 (18)	0.0312 (18)	0.0350 (17)	−0.0060 (14)	−0.0026 (14)	−0.0025 (14)
C23	0.0371 (19)	0.041 (2)	0.0312 (16)	−0.0160 (16)	−0.0011 (14)	−0.0027 (14)
C24	0.0355 (19)	0.041 (2)	0.0337 (17)	−0.0143 (15)	−0.0070 (14)	−0.0017 (14)
C25	0.0270 (17)	0.0363 (19)	0.0337 (16)	−0.0077 (14)	−0.0026 (13)	−0.0032 (14)
C26	0.0375 (19)	0.0394 (19)	0.0311 (16)	−0.0115 (15)	−0.0037 (14)	−0.0017 (14)
C27	0.0374 (19)	0.0402 (19)	0.0301 (16)	−0.0127 (15)	−0.0051 (13)	−0.0075 (14)
C28	0.041 (2)	0.0344 (19)	0.0426 (19)	−0.0109 (16)	−0.0033 (15)	−0.0036 (15)
C29	0.0341 (18)	0.0375 (19)	0.0349 (17)	−0.0127 (15)	−0.0010 (14)	−0.0004 (14)
C30	0.042 (2)	0.039 (2)	0.0399 (18)	−0.0156 (16)	−0.0046 (15)	0.0048 (16)
N1	0.084 (2)	0.078 (2)	0.0487 (19)	−0.046 (2)	−0.0059 (17)	0.0056 (17)
N2	0.057 (2)	0.0517 (19)	0.0485 (17)	−0.0220 (16)	−0.0089 (14)	−0.0081 (15)
N3	0.0573 (19)	0.0487 (18)	0.0401 (16)	−0.0203 (15)	−0.0014 (13)	0.0024 (14)
N4	0.068 (2)	0.057 (2)	0.0525 (18)	−0.0300 (17)	−0.0186 (16)	0.0000 (15)
C31	0.044 (2)	0.040 (2)	0.0372 (18)	−0.0209 (16)	−0.0039 (15)	0.0065 (15)
C32	0.0374 (18)	0.0321 (18)	0.0297 (16)	−0.0145 (15)	−0.0013 (13)	0.0004 (13)
C33	0.0380 (19)	0.0347 (19)	0.0369 (18)	−0.0169 (15)	−0.0028 (14)	0.0024 (15)
C34	0.0420 (19)	0.0322 (18)	0.0293 (16)	−0.0177 (15)	−0.0044 (13)	−0.0014 (13)
C35	0.0319 (17)	0.0290 (17)	0.0322 (16)	−0.0099 (14)	−0.0016 (13)	0.0007 (13)
C36	0.0418 (19)	0.0366 (19)	0.0274 (16)	−0.0160 (16)	−0.0030 (14)	0.0013 (14)
N5	0.082 (2)	0.061 (2)	0.0447 (17)	−0.0440 (18)	−0.0137 (16)	0.0035 (15)
N6	0.0580 (19)	0.0476 (18)	0.0411 (16)	−0.0272 (15)	−0.0024 (13)	0.0049 (14)

Geometric parameters (Å, º) top

C1—C1A	1.390 (4)	C13'—C14'	1.385 (4)
C1—C2	1.390 (4)	C13'—C18'	1.394 (4)
C1—H1	0.9500	C14'—C15'	1.383 (4)
C1A—C4A	1.401 (4)	C14'—H14'	0.9500
C1A—C9	1.471 (4)	C15'—C16'	1.380 (5)
C2—C3	1.395 (4)	C15'—H15'	0.9500
C2—H2	0.9500	C16'—C17'	1.373 (5)
C3—C4	1.387 (4)	C16'—H16'	0.9500
C3—H3	0.9500	C17'—C18'	1.376 (5)
C4—C4A	1.385 (4)	C17'—H17'	0.9500
C4—H4	0.9500	C18'—H18'	0.9500
C4A—C5A	1.459 (4)	C19—N1	1.146 (4)
C5—C6	1.389 (4)	C19—C20	1.433 (4)
C5—C5A	1.391 (4)	C20—C22	1.381 (4)
C5—H5	0.9500	C20—C21	1.433 (4)
C5A—C8A	1.418 (4)	C21—N2	1.151 (4)
C6—C7	1.382 (4)	C22—C23	1.431 (4)
C6—H6	0.9500	C22—C27	1.450 (4)
C7—C8	1.382 (4)	C23—C24	1.339 (4)
C7—H7	0.9500	C23—H23	0.9500
C8—C8A	1.383 (4)	C24—C25	1.445 (4)
C8—H8	0.9500	C24—H24	0.9500
C8A—C9	1.481 (4)	C25—C29	1.374 (4)
C9—C10	1.369 (4)	C25—C26	1.432 (4)
C10—C11'	1.437 (4)	C26—C27	1.344 (4)
C10—C11	1.441 (4)	C26—H26	0.9500
C11—C12	1.203 (4)	C27—H27	0.9500
C12—C13	1.427 (4)	C28—N3	1.141 (3)
C13—C14	1.398 (4)	C28—C29	1.438 (4)
C13—C18	1.403 (4)	C29—C30	1.438 (4)
C14—C15	1.378 (4)	C30—N4	1.154 (4)
C14—H14	0.9500	C31—N5	1.152 (4)
C15—C16	1.384 (5)	C31—C32	1.432 (4)
C15—H15	0.9500	C32—C35	1.373 (4)
C16—C17	1.373 (5)	C32—C33	1.436 (4)
C16—H16	0.9500	C33—N6	1.143 (3)
C17—C18	1.381 (5)	C34—C36ⁱ	1.338 (4)
C17—H17	0.9500	C34—C35	1.443 (4)
C18—H18	0.9500	C34—H34	0.9500
C11'—C12'	1.195 (4)	C35—C36	1.440 (4)
C12'—C13'	1.429 (4)	C36—H36	0.9500

C1A—C1—C2	119.0 (3)	C12'—C11'—C10	172.8 (3)
C1A—C1—H1	120.5	C11'—C12'—C13'	178.8 (4)
C2—C1—H1	120.5	C14'—C13'—C18'	119.6 (3)
C1—C1A—C4A	119.9 (3)	C14'—C13'—C12'	120.9 (3)
C1—C1A—C9	132.1 (3)	C18'—C13'—C12'	119.5 (3)
C4A—C1A—C9	108.0 (3)	C15'—C14'—C13'	120.0 (4)
C1—C2—C3	121.2 (3)	C15'—C14'—H14'	120.0
C1—C2—H2	119.4	C13'—C14'—H14'	120.0
C3—C2—H2	119.4	C16'—C15'—C14'	120.4 (4)
C4—C3—C2	119.6 (3)	C16'—C15'—H15'	119.8
C4—C3—H3	120.2	C14'—C15'—H15'	119.8
C2—C3—H3	120.2	C17'—C16'—C15'	119.3 (4)
C4A—C4—C3	119.6 (3)	C17'—C16'—H16'	120.3
C4A—C4—H4	120.2	C15'—C16'—H16'	120.3
C3—C4—H4	120.2	C16'—C17'—C18'	121.4 (4)
C4—C4A—C1A	120.7 (3)	C16'—C17'—H17'	119.3
C4—C4A—C5A	130.2 (3)	C18'—C17'—H17'	119.3
C1A—C4A—C5A	109.1 (3)	C17'—C18'—C13'	119.3 (4)
C6—C5—C5A	118.9 (3)	C17'—C18'—H18'	120.4
C6—C5—H5	120.6	C13'—C18'—H18'	120.4
C5A—C5—H5	120.6	N1—C19—C20	178.0 (4)
C5—C5A—C8A	120.5 (3)	C22—C20—C19	122.8 (3)
C5—C5A—C4A	130.9 (3)	C22—C20—C21	121.8 (3)
C8A—C5A—C4A	108.6 (3)	C19—C20—C21	115.3 (3)
C7—C6—C5	120.3 (3)	N2—C21—C20	179.2 (3)
C7—C6—H6	119.8	C20—C22—C23	121.9 (3)
C5—C6—H6	119.8	C20—C22—C27	120.6 (3)
C8—C7—C6	121.5 (3)	C23—C22—C27	117.4 (3)
C8—C7—H7	119.3	C24—C23—C22	120.9 (3)
C6—C7—H7	119.3	C24—C23—H23	119.6
C7—C8—C8A	119.4 (3)	C22—C23—H23	119.6
C7—C8—H8	120.3	C23—C24—C25	121.9 (3)
C8A—C8—H8	120.3	C23—C24—H24	119.0
C8—C8A—C5A	119.5 (3)	C25—C24—H24	119.0
C8—C8A—C9	133.2 (3)	C29—C25—C26	122.2 (3)
C5A—C8A—C9	107.3 (3)	C29—C25—C24	120.5 (3)
C10—C9—C1A	127.2 (3)	C26—C25—C24	117.3 (3)
C10—C9—C8A	125.8 (3)	C27—C26—C25	120.9 (3)
C1A—C9—C8A	106.9 (2)	C27—C26—H26	119.6
C9—C10—C11'	123.5 (3)	C25—C26—H26	119.6
C9—C10—C11	124.4 (3)	C26—C27—C22	121.6 (3)
C11'—C10—C11	112.0 (3)	C26—C27—H27	119.2
C12—C11—C10	173.3 (3)	C22—C27—H27	119.2
C11—C12—C13	177.1 (3)	N3—C28—C29	178.4 (4)
C14—C13—C18	118.9 (3)	C25—C29—C28	123.8 (3)
C14—C13—C12	121.0 (3)	C25—C29—C30	120.9 (3)
C18—C13—C12	120.1 (3)	C28—C29—C30	115.3 (3)
C15—C14—C13	121.2 (3)	N4—C30—C29	178.6 (4)
C15—C14—H14	119.4	N5—C31—C32	178.9 (3)
C13—C14—H14	119.4	C35—C32—C31	121.1 (3)
C14—C15—C16	119.0 (4)	C35—C32—C33	122.8 (3)
C14—C15—H15	120.5	C31—C32—C33	116.1 (3)
C16—C15—H15	120.5	N6—C33—C32	178.4 (4)
C17—C16—C15	120.9 (4)	C36ⁱ—C34—C35	121.8 (3)
C17—C16—H16	119.6	C36ⁱ—C34—H34	119.1
C15—C16—H16	119.6	C35—C34—H34	119.1
C16—C17—C18	120.8 (3)	C32—C35—C36	120.9 (3)
C16—C17—H17	119.6	C32—C35—C34	121.8 (3)
C18—C17—H17	119.6	C36—C35—C34	117.3 (3)
C17—C18—C13	119.3 (3)	C34ⁱ—C36—C35	120.9 (3)
C17—C18—H18	120.3	C34ⁱ—C36—H36	119.5
C13—C18—H18	120.3	C35—C36—H36	119.5

C2—C1—C1A—C4A	−1.0 (4)	C13—C14—C15—C16	0.1 (5)
C2—C1—C1A—C9	178.8 (3)	C14—C15—C16—C17	−0.8 (5)
C1A—C1—C2—C3	−0.3 (5)	C15—C16—C17—C18	0.7 (5)
C1—C2—C3—C4	1.1 (5)	C16—C17—C18—C13	0.0 (5)
C2—C3—C4—C4A	−0.6 (5)	C14—C13—C18—C17	−0.7 (4)
C3—C4—C4A—C1A	−0.6 (5)	C18'—C13'—C14'—C15'	2.0 (5)
C3—C4—C4A—C5A	178.8 (3)	C12'—C13'—C14'—C15'	−177.2 (3)
C1—C1A—C4A—C4	1.4 (4)	C13'—C14'—C15'—C16'	−1.9 (6)
C9—C1A—C4A—C4	−178.4 (3)	C14'—C15'—C16'—C17'	0.3 (6)
C1—C1A—C4A—C5A	−178.1 (3)	C15'—C16'—C17'—C18'	1.1 (6)
C9—C1A—C4A—C5A	2.1 (3)	C16'—C17'—C18'—C13'	−1.0 (6)
C6—C5—C5A—C8A	1.1 (4)	C14'—C13'—C18'—C17'	−0.6 (5)
C6—C5—C5A—C4A	−178.5 (3)	C12'—C13'—C18'—C17'	178.6 (3)
C4—C4A—C5A—C5	−0.1 (5)	C19—C20—C22—C23	−5.0 (5)
C1A—C4A—C5A—C5	179.4 (3)	C21—C20—C22—C23	176.2 (3)
C4—C4A—C5A—C8A	−179.7 (3)	C19—C20—C22—C27	173.9 (3)
C1A—C4A—C5A—C8A	−0.2 (3)	C21—C20—C22—C27	−4.9 (4)
C5A—C5—C6—C7	−0.5 (4)	C20—C22—C23—C24	177.9 (3)
C5—C6—C7—C8	−0.3 (5)	C27—C22—C23—C24	−1.0 (4)
C6—C7—C8—C8A	0.5 (5)	C22—C23—C24—C25	−1.2 (4)
C7—C8—C8A—C5A	0.2 (4)	C23—C24—C25—C29	−176.9 (3)
C7—C8—C8A—C9	−179.3 (3)	C23—C24—C25—C26	2.7 (4)
C5—C5A—C8A—C8	−1.0 (4)	C29—C25—C26—C27	177.5 (3)
C4A—C5A—C8A—C8	178.7 (3)	C24—C25—C26—C27	−2.1 (4)
C5—C5A—C8A—C9	178.6 (3)	C25—C26—C27—C22	0.0 (4)
C4A—C5A—C8A—C9	−1.7 (3)	C20—C22—C27—C26	−177.3 (3)
C1—C1A—C9—C10	−5.6 (5)	C23—C22—C27—C26	1.6 (4)
C4A—C1A—C9—C10	174.2 (3)	C26—C25—C29—C28	2.1 (5)
C1—C1A—C9—C8A	177.1 (3)	C24—C25—C29—C28	−178.4 (3)
C4A—C1A—C9—C8A	−3.1 (3)	C26—C25—C29—C30	−177.3 (3)
C8—C8A—C9—C10	5.1 (5)	C24—C25—C29—C30	2.3 (4)
C5A—C8A—C9—C10	−174.4 (3)	C31—C32—C35—C36	−179.4 (3)
C8—C8A—C9—C1A	−177.5 (3)	C33—C32—C35—C36	0.2 (4)
C5A—C8A—C9—C1A	3.0 (3)	C31—C32—C35—C34	−0.1 (4)
C1A—C9—C10—C11'	0.4 (5)	C33—C32—C35—C34	179.5 (3)
C8A—C9—C10—C11'	177.2 (3)	C36ⁱ—C34—C35—C32	−178.7 (3)
C1A—C9—C10—C11	−178.3 (3)	C36ⁱ—C34—C35—C36	0.7 (5)
C8A—C9—C10—C11	−1.5 (5)	C32—C35—C36—C34ⁱ	178.7 (3)
C18—C13—C14—C15	0.6 (5)	C34—C35—C36—C34ⁱ	−0.6 (5)
C12—C13—C14—C15	−177.4 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36···N2ⁱ	0.95	2.49	3.389 (4)	159
C6—H6···N3	0.95	2.71	3.436 (4)	134
C6—H6···N5	0.95	2.78	3.501 (5)	134
C26—H26···N5	0.95	2.58	3.480 (4)	157
C14—H14···N6	0.95	2.67	3.464 (4)	141
C2—H2···N4ⁱⁱ	0.95	2.78	3.651 (5)	152

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y, −z+1.

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