10,10-Bis­(tri­methyl­silyl­ethynyl)-9-methyl­enefluorene-tetra­cyano-para-quinodi­methane (2/1)

The title compound {systematic name: 9-[bis­(tri­methylsilyl­ethynyl)­methyl­ene]­fluorene-tetra­cyano-para-quinodimeth­ane (2/1)}, 2 C₂₄H₂₆Si₂·C₁₂H₄N₄, consists of sandwich-like fluorene-TCNQ-fluorene units with inversion symmetry. The ring systems of the sandwich are parallel; the interplanar separation is 3.3-3.4 Å. The packing of the sandwich units is a herringbone pattern.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.111
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.68 Ratio

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            black,
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            lustrous
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
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Si2    -   C12     ..       5.72 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11'    ..       5.33 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4'    -   C6'     ..       5.05 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Si1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Si2
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  C4'    -   C5'    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4'    -   C6'    ...       1.43 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  N1      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14C   ..  N1      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15B   ..  N1      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13C   ..  N2      ..       2.73 Ang.

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

   5 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
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); 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-[bis(trimethylsilylethynyl)methylene]fluorene–tetracyano-para-quinodimethane (2/1)

Crystal data

2C24H26Si2·C12H4N4	F(000) = 1000
Mr = 945.44	Dx = 1.143 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.933 (2) Å	Cell parameters from 46 reflections
b = 18.398 (4) Å	θ = 10–11.5°
c = 12.509 (3) Å	µ = 0.15 mm^−1
β = 90.85 (3)°	T = 143 K
V = 2746.0 (10) Å^3	Block, violet-black, lustrous
Z = 2	0.6 × 0.5 × 0.4 mm

Data collection

Stoe STADI-4 diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.2°
Graphite monochromator	h = −14→14
ω/θ–scan	k = −21→13
8921 measured reflections	l = −14→0
4831 independent reflections	3 standard reflections every 60 min
3827 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 1.3032P] where P = (Fo^2 + 2Fc^2)/3
4831 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.30 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)

2.9216 (0.0035) x + 10.3723 (0.0075) y + 9.8207 (0.0057) z = 8.2091 (0.0047)

* 0.0752 (0.0018) C1 * 0.0727 (0.0018) C2 * -0.0002 (0.0018) C3 * -0.0630 (0.0019) C4 * -0.0200 (0.0021) C5 * 0.0515 (0.0021) C6 * 0.0726 (0.0021) C7 * 0.0295 (0.0020) C8 * 0.0004 (0.0017) C1A * -0.0535 (0.0018) C4A * -0.0627 (0.0019) C5A * -0.0385 (0.0018) C8A * -0.0180 (0.0017) C9 * 0.0007 (0.0016) C10 * -0.0468 (0.0015) C11 0.1196 (0.0023) C11' 0.2722 (0.0027) C12' -0.0745 (0.0026) C12 0.6106 (0.0023) Si1 - 0.1040 (0.0021) Si2

Rms deviation of fitted atoms = 0.0482

2.7852 (0.0067) x + 10.2041 (0.0101) y + 9.9464 (0.0066) z = 11.4578 (0.0073)

Angle to previous plane (with approximate e.s.d.) = 1.01 (0.07)

* 0.0279 (0.0015) C1' * -0.0030 (0.0017) C2' * -0.0235 (0.0015) C3' * -0.0039 (0.0019) C4' * -0.0070 (0.0020) C5' * 0.0035 (0.0019) C6' * -0.0086 (0.0015) N1 * 0.0146 (0.0015) N2

Rms deviation of fitted atoms = 0.0146

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
Si1	0.56796 (5)	0.17729 (4)	0.54186 (5)	0.03851 (18)
Si2	0.01140 (5)	0.28596 (3)	0.51990 (5)	0.03702 (17)
C1	0.58348 (16)	0.37469 (11)	0.27425 (16)	0.0307 (5)
H1	0.5921	0.3338	0.3201	0.037*
C1A	0.47973 (15)	0.40852 (11)	0.26177 (14)	0.0265 (4)
C2	0.67387 (17)	0.40171 (12)	0.21856 (17)	0.0375 (5)
H2	0.7450	0.3790	0.2265	0.045*
C3	0.66255 (18)	0.46110 (12)	0.15178 (18)	0.0390 (5)
H3	0.7257	0.4784	0.1140	0.047*
C4	0.56010 (17)	0.49585 (12)	0.13916 (17)	0.0366 (5)
H4	0.5524	0.5368	0.0933	0.044*
C4A	0.46931 (16)	0.46952 (11)	0.19495 (15)	0.0285 (4)
C5	0.30409 (19)	0.55703 (12)	0.15509 (18)	0.0410 (5)
H5	0.3451	0.5876	0.1086	0.049*
C5A	0.35357 (16)	0.49622 (11)	0.20025 (15)	0.0307 (4)
C6	0.1934 (2)	0.57263 (13)	0.1788 (2)	0.0483 (6)
H6	0.1583	0.6144	0.1487	0.058*
C7	0.13389 (19)	0.52780 (13)	0.2460 (2)	0.0455 (6)
H7	0.0581	0.5391	0.2612	0.055*
C8	0.18256 (16)	0.46647 (12)	0.29193 (17)	0.0358 (5)
H8	0.1409	0.4361	0.3381	0.043*
C8A	0.29322 (16)	0.45048 (11)	0.26897 (15)	0.0278 (4)
C9	0.36950 (15)	0.39291 (10)	0.30916 (14)	0.0255 (4)
C10	0.34421 (15)	0.33748 (11)	0.37713 (15)	0.0264 (4)
C11	0.23409 (16)	0.32493 (11)	0.41831 (15)	0.0293 (4)
C12	0.14594 (17)	0.30960 (11)	0.45791 (16)	0.0338 (5)
C13	−0.0161 (2)	0.18845 (13)	0.49489 (19)	0.0447 (6)
H13A	−0.0873	0.1747	0.5273	0.054*
H13B	0.0447	0.1593	0.5264	0.054*
H13C	−0.0203	0.1796	0.4177	0.054*
C14	−0.0988 (2)	0.34298 (19)	0.4576 (3)	0.0944 (13)
H14A	−0.1711	0.3320	0.4900	0.113*
H14B	−0.1031	0.3328	0.3807	0.113*
H14C	−0.0807	0.3944	0.4688	0.113*
C15	0.0271 (3)	0.30316 (14)	0.6653 (2)	0.0673 (9)
H15A	−0.0401	0.2862	0.7019	0.081*
H15B	0.0369	0.3554	0.6777	0.081*
H15C	0.0928	0.2770	0.6931	0.081*
C11'	0.42512 (16)	0.28655 (11)	0.41897 (15)	0.0289 (4)
C12'	0.48550 (17)	0.24310 (12)	0.46243 (16)	0.0344 (5)
C13'	0.4636 (2)	0.1222 (2)	0.6131 (3)	0.0882 (12)
H13D	0.5023	0.0866	0.6588	0.106*
H13E	0.4156	0.0968	0.5611	0.106*
H13F	0.4176	0.1540	0.6574	0.106*
C14'	0.6546 (2)	0.12195 (18)	0.4533 (3)	0.0747 (9)
H14D	0.7020	0.0894	0.4964	0.090*
H14E	0.7020	0.1538	0.4105	0.090*
H14F	0.6061	0.0931	0.4058	0.090*
C15'	0.6561 (2)	0.22957 (16)	0.6370 (2)	0.0596 (7)
H15D	0.7063	0.1964	0.6759	0.071*
H15E	0.6081	0.2549	0.6879	0.071*
H15F	0.7007	0.2652	0.5978	0.071*
C1'	0.60780 (17)	0.47005 (12)	0.50233 (17)	0.0350 (5)
H1'	0.6813	0.4502	0.5030	0.042*
C2'	0.58497 (17)	0.53405 (11)	0.43996 (16)	0.0323 (5)
C3'	0.47208 (17)	0.56251 (12)	0.44032 (16)	0.0341 (5)
H3'	0.4542	0.6046	0.3996	0.041*
C4'	0.66707 (17)	0.56764 (12)	0.38242 (17)	0.0359 (5)
C5'	0.7796 (2)	0.54005 (13)	0.3789 (2)	0.0435 (6)
C6'	0.64684 (19)	0.63260 (14)	0.32218 (18)	0.0419 (5)
N1	0.86930 (18)	0.51887 (12)	0.3753 (2)	0.0612 (6)
N2	0.6314 (2)	0.68462 (13)	0.27426 (18)	0.0600 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0304 (3)	0.0419 (4)	0.0432 (4)	0.0045 (3)	0.0030 (3)	0.0134 (3)
Si2	0.0348 (3)	0.0308 (3)	0.0460 (4)	0.0051 (3)	0.0154 (3)	0.0107 (3)
C1	0.0299 (10)	0.0342 (12)	0.0282 (10)	−0.0003 (9)	0.0019 (8)	−0.0004 (9)
C1A	0.0276 (10)	0.0301 (11)	0.0219 (9)	−0.0030 (8)	0.0015 (8)	−0.0049 (8)
C2	0.0291 (11)	0.0447 (13)	0.0388 (12)	−0.0002 (9)	0.0047 (9)	−0.0031 (10)
C3	0.0355 (11)	0.0433 (13)	0.0383 (12)	−0.0082 (10)	0.0104 (9)	−0.0008 (10)
C4	0.0426 (12)	0.0347 (12)	0.0325 (11)	−0.0069 (10)	0.0064 (9)	0.0003 (9)
C4A	0.0322 (10)	0.0302 (11)	0.0230 (10)	−0.0035 (8)	0.0012 (8)	−0.0032 (8)
C5	0.0452 (13)	0.0340 (12)	0.0437 (13)	0.0008 (10)	0.0024 (10)	0.0087 (10)
C5A	0.0331 (10)	0.0327 (11)	0.0263 (10)	−0.0001 (9)	−0.0013 (8)	−0.0017 (9)
C6	0.0456 (13)	0.0398 (14)	0.0593 (16)	0.0097 (11)	−0.0025 (12)	0.0108 (12)
C7	0.0336 (11)	0.0427 (14)	0.0603 (15)	0.0084 (10)	0.0011 (11)	0.0030 (12)
C8	0.0287 (10)	0.0364 (12)	0.0422 (12)	0.0004 (9)	0.0022 (9)	0.0007 (10)
C8A	0.0299 (10)	0.0275 (11)	0.0261 (10)	−0.0015 (8)	−0.0020 (8)	−0.0025 (8)
C9	0.0261 (9)	0.0273 (11)	0.0232 (9)	−0.0011 (8)	−0.0014 (8)	−0.0046 (8)
C10	0.0271 (10)	0.0296 (11)	0.0224 (9)	−0.0004 (8)	0.0004 (8)	−0.0024 (8)
C11	0.0346 (11)	0.0307 (11)	0.0226 (10)	0.0000 (9)	−0.0006 (8)	0.0005 (8)
C12	0.0355 (11)	0.0351 (12)	0.0309 (11)	0.0013 (9)	0.0036 (9)	0.0032 (9)
C13	0.0462 (13)	0.0433 (14)	0.0447 (13)	−0.0058 (11)	0.0025 (11)	0.0006 (11)
C14	0.0456 (16)	0.088 (2)	0.150 (3)	0.0250 (16)	0.0263 (19)	0.067 (2)
C15	0.112 (2)	0.0372 (15)	0.0534 (16)	−0.0134 (15)	0.0434 (16)	−0.0074 (12)
C11'	0.0319 (10)	0.0322 (11)	0.0227 (10)	−0.0039 (9)	0.0050 (8)	−0.0002 (9)
C12'	0.0351 (11)	0.0381 (12)	0.0301 (11)	0.0008 (10)	0.0039 (9)	0.0045 (9)
C13'	0.0529 (17)	0.107 (3)	0.105 (3)	−0.0118 (17)	−0.0024 (17)	0.072 (2)
C14'	0.0641 (18)	0.080 (2)	0.079 (2)	0.0340 (17)	−0.0051 (16)	−0.0156 (18)
C15'	0.0565 (16)	0.0713 (19)	0.0505 (15)	0.0074 (14)	−0.0121 (12)	0.0088 (14)
C1'	0.0323 (11)	0.0365 (12)	0.0361 (11)	0.0023 (9)	−0.0030 (9)	−0.0099 (10)
C2'	0.0349 (11)	0.0335 (12)	0.0286 (10)	−0.0018 (9)	−0.0012 (8)	−0.0095 (9)
C3'	0.0383 (11)	0.0328 (12)	0.0311 (11)	0.0005 (9)	−0.0037 (9)	−0.0051 (9)
C4'	0.0385 (11)	0.0348 (12)	0.0344 (11)	−0.0021 (9)	0.0028 (9)	−0.0083 (10)
C5'	0.0421 (13)	0.0367 (13)	0.0521 (14)	−0.0070 (11)	0.0100 (11)	−0.0052 (11)
C6'	0.0435 (13)	0.0476 (15)	0.0348 (12)	−0.0048 (11)	0.0070 (10)	−0.0060 (11)
N1	0.0434 (12)	0.0455 (13)	0.0954 (18)	−0.0043 (10)	0.0182 (12)	0.0016 (12)
N2	0.0717 (15)	0.0581 (15)	0.0504 (13)	0.0017 (12)	0.0060 (11)	0.0065 (12)

Geometric parameters (Å, º)

Si1—C14'	1.835 (3)	C10—C11	1.437 (3)
Si1—C12'	1.842 (2)	C10—C11'	1.438 (3)
Si1—C13'	1.845 (3)	C11—C12	1.203 (3)
Si1—C15'	1.847 (3)	C13—H13A	0.9800
Si2—C12	1.845 (2)	C13—H13B	0.9800
Si2—C14	1.846 (3)	C13—H13C	0.9800
Si2—C13	1.850 (2)	C14—H14A	0.9800
Si2—C15	1.852 (3)	C14—H14B	0.9800
C1—C2	1.385 (3)	C14—H14C	0.9800
C1—C1A	1.392 (3)	C15—H15A	0.9800
C1—H1	0.9500	C15—H15B	0.9800
C1A—C4A	1.404 (3)	C15—H15C	0.9800
C1A—C9	1.479 (3)	C11'—C12'	1.201 (3)
C2—C3	1.381 (3)	C13'—H13D	0.9800
C2—H2	0.9500	C13'—H13E	0.9800
C3—C4	1.387 (3)	C13'—H13F	0.9800
C3—H3	0.9500	C14'—H14D	0.9800
C4—C4A	1.385 (3)	C14'—H14E	0.9800
C4—H4	0.9500	C14'—H14F	0.9800
C4A—C5A	1.468 (3)	C15'—H15D	0.9800
C5—C5A	1.382 (3)	C15'—H15E	0.9800
C5—C6	1.389 (3)	C15'—H15F	0.9800
C5—H5	0.9500	C1'—C3'^i	1.343 (3)
C5A—C8A	1.409 (3)	C1'—C2'	1.436 (3)
C6—C7	1.381 (3)	C1'—H1'	0.9500
C6—H6	0.9500	C2'—C4'	1.371 (3)
C7—C8	1.389 (3)	C2'—C3'	1.445 (3)
C7—H7	0.9500	C3'—H3'	0.9500
C8—C8A	1.387 (3)	C4'—C6'	1.432 (3)
C8—H8	0.9500	C4'—C5'	1.437 (3)
C8A—C9	1.480 (3)	C5'—N1	1.141 (3)
C9—C10	1.364 (3)	C6'—N2	1.143 (3)
C14'—Si1—C12'	109.91 (12)	C12—C11—C10	174.3 (2)
C14'—Si1—C13'	112.16 (18)	C11—C12—Si2	179.4 (2)
C12'—Si1—C13'	105.24 (12)	Si2—C13—H13A	109.5
C14'—Si1—C15'	110.94 (14)	Si2—C13—H13B	109.5
C12'—Si1—C15'	107.45 (12)	H13A—C13—H13B	109.5
C13'—Si1—C15'	110.88 (15)	Si2—C13—H13C	109.5
C12—Si2—C14	107.89 (12)	H13A—C13—H13C	109.5
C12—Si2—C13	108.12 (10)	H13B—C13—H13C	109.5
C14—Si2—C13	110.87 (15)	Si2—C14—H14A	109.5
C12—Si2—C15	107.23 (12)	Si2—C14—H14B	109.5
C14—Si2—C15	112.25 (17)	H14A—C14—H14B	109.5
C13—Si2—C15	110.30 (11)	Si2—C14—H14C	109.5
C2—C1—C1A	118.74 (19)	H14A—C14—H14C	109.5
C2—C1—H1	120.6	H14B—C14—H14C	109.5
C1A—C1—H1	120.6	Si2—C15—H15A	109.5
C1—C1A—C4A	119.67 (18)	Si2—C15—H15B	109.5
C1—C1A—C9	131.52 (18)	H15A—C15—H15B	109.5
C4A—C1A—C9	108.81 (16)	Si2—C15—H15C	109.5
C3—C2—C1	121.2 (2)	H15A—C15—H15C	109.5
C3—C2—H2	119.4	H15B—C15—H15C	109.5
C1—C2—H2	119.4	C12'—C11'—C10	173.4 (2)
C2—C3—C4	120.8 (2)	C11'—C12'—Si1	173.70 (18)
C2—C3—H3	119.6	Si1—C13'—H13D	109.5
C4—C3—H3	119.6	Si1—C13'—H13E	109.5
C4A—C4—C3	118.5 (2)	H13D—C13'—H13E	109.5
C4A—C4—H4	120.8	Si1—C13'—H13F	109.5
C3—C4—H4	120.8	H13D—C13'—H13F	109.5
C4—C4A—C1A	121.11 (19)	H13E—C13'—H13F	109.5
C4—C4A—C5A	130.48 (19)	Si1—C14'—H14D	109.5
C1A—C4A—C5A	108.40 (17)	Si1—C14'—H14E	109.5
C5A—C5—C6	118.8 (2)	H14D—C14'—H14E	109.5
C5A—C5—H5	120.6	Si1—C14'—H14F	109.5
C6—C5—H5	120.6	H14D—C14'—H14F	109.5
C5—C5A—C8A	120.92 (19)	H14E—C14'—H14F	109.5
C5—C5A—C4A	130.46 (19)	Si1—C15'—H15D	109.5
C8A—C5A—C4A	108.51 (17)	Si1—C15'—H15E	109.5
C7—C6—C5	120.4 (2)	H15D—C15'—H15E	109.5
C7—C6—H6	119.8	Si1—C15'—H15F	109.5
C5—C6—H6	119.8	H15D—C15'—H15F	109.5
C6—C7—C8	121.4 (2)	H15E—C15'—H15F	109.5
C6—C7—H7	119.3	C3'^i—C1'—C2'	121.71 (19)
C8—C7—H7	119.3	C3'^i—C1'—H1'	119.1
C8A—C8—C7	118.7 (2)	C2'—C1'—H1'	119.1
C8A—C8—H8	120.7	C4'—C2'—C1'	121.55 (19)
C7—C8—H8	120.7	C4'—C2'—C3'	120.8 (2)
C8—C8A—C5A	119.78 (19)	C1'—C2'—C3'	117.69 (19)
C8—C8A—C9	131.61 (19)	C1'^i—C3'—C2'	120.6 (2)
C5A—C8A—C9	108.51 (16)	C1'^i—C3'—H3'	119.7
C10—C9—C1A	126.95 (17)	C2'—C3'—H3'	119.7
C10—C9—C8A	127.31 (17)	C2'—C4'—C6'	122.4 (2)
C1A—C9—C8A	105.73 (16)	C2'—C4'—C5'	122.1 (2)
C9—C10—C11	123.73 (18)	C6'—C4'—C5'	115.4 (2)
C9—C10—C11'	124.07 (17)	N1—C5'—C4'	179.1 (3)
C11—C10—C11'	112.16 (17)	N2—C6'—C4'	179.5 (3)
C2—C1—C1A—C4A	−1.0 (3)	C4A—C5A—C8A—C8	176.62 (18)
C2—C1—C1A—C9	179.96 (19)	C5—C5A—C8A—C9	−176.84 (19)
C1A—C1—C2—C3	0.1 (3)	C4A—C5A—C8A—C9	−0.2 (2)
C1—C2—C3—C4	0.5 (3)	C1—C1A—C9—C10	−2.0 (3)
C2—C3—C4—C4A	−0.1 (3)	C4A—C1A—C9—C10	178.95 (18)
C3—C4—C4A—C1A	−0.8 (3)	C1—C1A—C9—C8A	177.1 (2)
C3—C4—C4A—C5A	177.6 (2)	C4A—C1A—C9—C8A	−1.9 (2)
C1—C1A—C4A—C4	1.4 (3)	C8—C8A—C9—C10	4.1 (3)
C9—C1A—C4A—C4	−179.36 (18)	C5A—C8A—C9—C10	−179.61 (19)
C1—C1A—C4A—C5A	−177.35 (17)	C8—C8A—C9—C1A	−175.0 (2)
C9—C1A—C4A—C5A	1.9 (2)	C5A—C8A—C9—C1A	1.3 (2)
C6—C5—C5A—C8A	0.2 (3)	C1A—C9—C10—C11	−178.68 (18)
C6—C5—C5A—C4A	−175.6 (2)	C8A—C9—C10—C11	2.4 (3)
C4—C4A—C5A—C5	−3.5 (4)	C1A—C9—C10—C11'	3.7 (3)
C1A—C4A—C5A—C5	175.2 (2)	C8A—C9—C10—C11'	−175.20 (18)
C4—C4A—C5A—C8A	−179.7 (2)	C3'^i—C1'—C2'—C4'	179.3 (2)
C1A—C4A—C5A—C8A	−1.0 (2)	C3'^i—C1'—C2'—C3'	−0.3 (3)
C5A—C5—C6—C7	−0.3 (4)	C4'—C2'—C3'—C1'^i	−179.27 (19)
C5—C6—C7—C8	0.3 (4)	C1'—C2'—C3'—C1'^i	0.3 (3)
C6—C7—C8—C8A	−0.1 (4)	C1'—C2'—C4'—C6'	−178.20 (19)
C7—C8—C8A—C5A	0.0 (3)	C3'—C2'—C4'—C6'	1.3 (3)
C7—C8—C8A—C9	175.9 (2)	C1'—C2'—C4'—C5'	1.5 (3)
C5—C5A—C8A—C8	0.0 (3)	C3'—C2'—C4'—C5'	−178.9 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1^ii	0.95	2.71	3.573 (3)	151
C14—H14C···N1^ii	0.98	2.64	3.415 (4)	137
C15—H15B···N1^i	0.98	2.66	3.539 (3)	150
C13—H13C···N2^iii	0.98	2.73	3.619 (3)	152

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