An ion-pair complex composed of two N-(4-cyanobenzyl)quinolinium cations, two 7,7,8,8-tetracyanoquinodimethane anions and one neutral 7,7,8,8-tetracyanoquinodimethane molecule

In the title complex, 2C₁₇H₁₃N₂⁺·2C₁₂H₄N₄⁻·C₁₂H₄N₄, a bound unit of two anions and one neutral TCNQ (TCNQ is 7,7,8,8-tetra­cyano­quinodimethane) molecule is formed and adjacent units are displaced relative to each other along the direction of the shorter mol­ecular axis of TCNQ. Completely segregated columnar stacks of TCNQ anions/molecules and cations are observed. Within an TCNQ column, the benzene rings are parallel to each other, the neutral TCNQ molecules lying on inversion centres. The centroid-to-centroid distance between adjacent aromatic rings is less than 4.2 Å and π–π stacking inter­actions are found.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.138
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
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
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       5.44 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.24
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C27    -   C28    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C27    -   C29    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C33    -   C34    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C33    -   C35    ...       1.42 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C22    ..  C34     ..       3.17 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

N-(4-cyanobenzyl)quinolinium–7,7,8,8-tetracyanoquinodimethane (2/3)

Crystal data

2C17H13N2^+·2C12H4N4^−·C12H4N4	F(000) = 1140
Mr = 1103.16	Dx = 1.346 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3296 reflections
a = 16.083 (3) Å	θ = 2.3–26.5°
b = 10.8627 (17) Å	µ = 0.08 mm^−1
c = 17.099 (3) Å	T = 293 K
β = 114.327 (3)°	Block, dark green
V = 2722.0 (7) Å^3	0.20 × 0.20 × 0.15 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5321 independent reflections
Radiation source: sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −19→19
Tmin = 0.983, Tmax = 0.988	k = −13→13
14142 measured reflections	l = −21→14

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) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + 0.5287P] where P = (Fo^2 + 2Fc^2)/3
5321 reflections	(Δ/σ)max < 0.001
388 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.34564 (13)	0.9686 (2)	0.22175 (12)	0.0796 (6)
N2	0.19916 (14)	1.0214 (2)	−0.04701 (12)	0.0762 (6)
N3	0.62204 (14)	0.7121 (2)	−0.14023 (15)	0.0821 (7)
N4	0.77818 (14)	0.6509 (2)	0.13440 (16)	0.0897 (7)
N5	0.35809 (13)	0.62120 (19)	0.17934 (12)	0.0719 (6)
N6	0.22321 (11)	0.71195 (19)	−0.09163 (12)	0.0653 (5)
N7	−0.11670 (13)	0.04670 (18)	0.49120 (12)	0.0656 (5)
N8	0.05696 (9)	0.42992 (13)	0.22015 (9)	0.0379 (3)
C1	−0.10134 (13)	0.11791 (19)	0.45041 (12)	0.0487 (5)
C2	−0.08183 (12)	0.20649 (17)	0.39781 (10)	0.0414 (4)
C3	0.00496 (12)	0.21083 (17)	0.39901 (11)	0.0435 (4)
H3	0.0511	0.1607	0.4363	0.052*
C4	0.02212 (11)	0.28969 (17)	0.34475 (10)	0.0407 (4)
H4	0.0803	0.2928	0.3457	0.049*
C5	−0.04558 (11)	0.36437 (16)	0.28893 (10)	0.0369 (4)
C6	−0.13159 (12)	0.36175 (18)	0.29008 (12)	0.0452 (4)
H6	−0.1774	0.4135	0.2539	0.054*
C7	−0.14914 (12)	0.28339 (18)	0.34417 (12)	0.0477 (5)
H7	−0.2067	0.2821	0.3446	0.057*
C8	−0.03095 (12)	0.45028 (17)	0.22680 (12)	0.0430 (4)
H8A	−0.0804	0.4397	0.1705	0.052*
H8B	−0.0331	0.5345	0.2448	0.052*
C9	0.12390 (13)	0.50912 (18)	0.25719 (11)	0.0460 (5)
H9	0.1147	0.5752	0.2873	0.055*
C10	0.20756 (13)	0.4967 (2)	0.25259 (12)	0.0534 (5)
H10	0.2534	0.5546	0.2783	0.064*
C11	0.22158 (12)	0.3999 (2)	0.21045 (12)	0.0529 (5)
H11	0.2772	0.3913	0.2064	0.063*
C12	0.15313 (11)	0.31195 (18)	0.17266 (11)	0.0436 (4)
C13	0.16457 (15)	0.2080 (2)	0.12908 (13)	0.0586 (6)
H13	0.2200	0.1956	0.1253	0.070*
C14	0.09696 (16)	0.1265 (2)	0.09297 (14)	0.0614 (6)
H14	0.1059	0.0578	0.0649	0.074*
C15	0.01301 (14)	0.14448 (19)	0.09735 (12)	0.0537 (5)
H15	−0.0335	0.0875	0.0717	0.064*
C16	−0.00195 (12)	0.24336 (17)	0.13821 (11)	0.0426 (4)
H16	−0.0583	0.2543	0.1403	0.051*
C17	0.06793 (11)	0.32850 (16)	0.17706 (10)	0.0369 (4)
C18	0.26579 (14)	0.9889 (2)	0.00643 (13)	0.0514 (5)
C19	0.34683 (12)	0.94830 (18)	0.07388 (11)	0.0446 (4)
C20	0.34779 (13)	0.9590 (2)	0.15652 (13)	0.0528 (5)
C21	0.41926 (11)	0.89603 (18)	0.05936 (11)	0.0440 (4)
C22	0.41549 (12)	0.88743 (18)	−0.02445 (12)	0.0469 (5)
H22	0.3648	0.9182	−0.0704	0.056*
C23	0.48412 (13)	0.83532 (19)	−0.03940 (12)	0.0495 (5)
H23	0.4793	0.8302	−0.0954	0.059*
C24	0.56275 (12)	0.78871 (19)	0.02838 (13)	0.0511 (5)
C25	0.56641 (12)	0.7975 (2)	0.11217 (13)	0.0549 (5)
H25	0.6170	0.7666	0.1581	0.066*
C26	0.49794 (12)	0.8497 (2)	0.12725 (12)	0.0518 (5)
H26	0.5029	0.8552	0.1833	0.062*
C27	0.63346 (13)	0.7336 (2)	0.01285 (14)	0.0583 (6)
C28	0.62766 (14)	0.7221 (2)	−0.07184 (17)	0.0630 (6)
C29	0.71356 (15)	0.6878 (2)	0.08023 (17)	0.0678 (7)
C30	0.42493 (11)	0.54602 (17)	−0.06944 (11)	0.0408 (4)
H30	0.3747	0.5772	−0.1155	0.049*
C31	0.42811 (11)	0.55431 (16)	0.01501 (11)	0.0386 (4)
C32	0.50671 (11)	0.50611 (17)	0.08362 (11)	0.0405 (4)
H32	0.5109	0.5108	0.1394	0.049*
C33	0.35852 (11)	0.60989 (18)	0.02995 (12)	0.0434 (4)
C34	0.28253 (12)	0.66475 (19)	−0.03757 (13)	0.0481 (5)
C35	0.35867 (12)	0.61575 (19)	0.11309 (13)	0.0504 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0605 (12)	0.132 (2)	0.0521 (11)	0.0007 (12)	0.0288 (9)	−0.0159 (11)
N2	0.0667 (13)	0.1008 (17)	0.0623 (12)	0.0324 (12)	0.0276 (10)	0.0040 (11)
N3	0.0810 (14)	0.0934 (17)	0.1049 (16)	−0.0064 (12)	0.0715 (13)	−0.0147 (13)
N4	0.0400 (11)	0.1110 (19)	0.1185 (18)	−0.0042 (12)	0.0331 (12)	−0.0188 (14)
N5	0.0730 (13)	0.0904 (15)	0.0736 (13)	−0.0024 (11)	0.0518 (11)	−0.0083 (11)
N6	0.0325 (9)	0.0851 (14)	0.0749 (12)	0.0076 (9)	0.0187 (9)	−0.0080 (10)
N7	0.0781 (13)	0.0675 (13)	0.0657 (11)	−0.0028 (10)	0.0443 (10)	0.0098 (9)
N8	0.0360 (8)	0.0436 (9)	0.0394 (8)	0.0038 (7)	0.0209 (6)	0.0077 (6)
C1	0.0548 (12)	0.0527 (12)	0.0462 (10)	−0.0058 (10)	0.0283 (9)	−0.0056 (9)
C2	0.0472 (10)	0.0458 (11)	0.0378 (9)	−0.0055 (9)	0.0242 (8)	−0.0068 (8)
C3	0.0405 (10)	0.0506 (11)	0.0377 (9)	0.0031 (8)	0.0146 (8)	0.0017 (8)
C4	0.0334 (9)	0.0500 (11)	0.0429 (9)	−0.0006 (8)	0.0200 (8)	−0.0006 (8)
C5	0.0369 (9)	0.0393 (10)	0.0395 (9)	0.0016 (8)	0.0209 (7)	−0.0034 (7)
C6	0.0381 (10)	0.0518 (12)	0.0519 (10)	0.0085 (9)	0.0249 (8)	0.0033 (9)
C7	0.0426 (10)	0.0563 (12)	0.0561 (11)	−0.0004 (9)	0.0324 (9)	−0.0020 (9)
C8	0.0398 (10)	0.0481 (11)	0.0503 (10)	0.0097 (8)	0.0278 (8)	0.0046 (8)
C9	0.0494 (11)	0.0493 (11)	0.0408 (9)	−0.0050 (9)	0.0202 (8)	0.0042 (8)
C10	0.0393 (10)	0.0712 (15)	0.0479 (11)	−0.0113 (10)	0.0162 (9)	0.0098 (10)
C11	0.0349 (10)	0.0777 (15)	0.0521 (11)	0.0055 (10)	0.0239 (9)	0.0190 (11)
C12	0.0367 (9)	0.0575 (12)	0.0435 (9)	0.0095 (9)	0.0236 (8)	0.0154 (9)
C13	0.0572 (13)	0.0702 (15)	0.0668 (13)	0.0180 (12)	0.0442 (11)	0.0096 (11)
C14	0.0780 (15)	0.0573 (14)	0.0662 (13)	0.0137 (12)	0.0470 (12)	0.0000 (11)
C15	0.0636 (13)	0.0542 (13)	0.0486 (11)	−0.0026 (10)	0.0285 (10)	0.0002 (9)
C16	0.0373 (9)	0.0523 (12)	0.0424 (9)	0.0040 (9)	0.0206 (8)	0.0068 (8)
C17	0.0352 (9)	0.0447 (10)	0.0367 (8)	0.0084 (8)	0.0207 (7)	0.0109 (7)
C18	0.0520 (12)	0.0593 (13)	0.0529 (11)	0.0078 (10)	0.0319 (10)	−0.0040 (10)
C19	0.0371 (10)	0.0555 (12)	0.0455 (10)	−0.0042 (9)	0.0212 (8)	−0.0085 (8)
C20	0.0374 (10)	0.0724 (15)	0.0517 (12)	−0.0012 (10)	0.0215 (9)	−0.0113 (10)
C21	0.0346 (9)	0.0537 (11)	0.0487 (10)	−0.0103 (9)	0.0223 (8)	−0.0113 (8)
C22	0.0412 (10)	0.0565 (12)	0.0485 (10)	−0.0071 (9)	0.0241 (8)	−0.0060 (9)
C23	0.0459 (11)	0.0595 (13)	0.0543 (11)	−0.0129 (9)	0.0317 (9)	−0.0142 (9)
C24	0.0354 (10)	0.0611 (13)	0.0652 (12)	−0.0155 (9)	0.0291 (9)	−0.0206 (10)
C25	0.0304 (9)	0.0736 (15)	0.0583 (12)	−0.0081 (10)	0.0158 (8)	−0.0196 (10)
C26	0.0362 (10)	0.0736 (14)	0.0478 (10)	−0.0078 (10)	0.0195 (8)	−0.0169 (10)
C27	0.0375 (11)	0.0685 (15)	0.0804 (14)	−0.0140 (10)	0.0359 (11)	−0.0233 (11)
C28	0.0500 (12)	0.0628 (15)	0.0986 (17)	−0.0127 (10)	0.0534 (13)	−0.0183 (13)
C29	0.0347 (12)	0.0795 (17)	0.0988 (17)	−0.0130 (12)	0.0371 (12)	−0.0290 (14)
C30	0.0283 (9)	0.0525 (11)	0.0417 (9)	−0.0003 (8)	0.0145 (7)	−0.0027 (8)
C31	0.0285 (9)	0.0444 (11)	0.0469 (10)	−0.0072 (8)	0.0195 (7)	−0.0074 (8)
C32	0.0328 (9)	0.0529 (11)	0.0396 (9)	−0.0035 (8)	0.0186 (8)	−0.0051 (8)
C33	0.0299 (9)	0.0507 (11)	0.0553 (10)	−0.0054 (8)	0.0233 (8)	−0.0078 (9)
C34	0.0286 (10)	0.0592 (13)	0.0630 (12)	−0.0042 (9)	0.0253 (9)	−0.0122 (10)
C35	0.0393 (10)	0.0594 (13)	0.0647 (12)	−0.0029 (9)	0.0337 (10)	−0.0074 (10)

Geometric parameters (Å, º)

N1—C20	1.135 (2)	C13—H13	0.9300
N2—C18	1.141 (3)	C14—C15	1.396 (3)
N3—C28	1.140 (3)	C14—H14	0.9300
N4—C29	1.143 (3)	C15—C16	1.356 (3)
N5—C35	1.138 (2)	C15—H15	0.9300
N6—C34	1.141 (2)	C16—C17	1.395 (2)
N7—C1	1.135 (2)	C16—H16	0.9300
N8—C9	1.319 (2)	C18—C19	1.409 (3)
N8—C17	1.376 (2)	C19—C21	1.407 (2)
N8—C8	1.481 (2)	C19—C20	1.412 (2)
C1—C2	1.437 (3)	C21—C26	1.411 (3)
C2—C7	1.376 (3)	C21—C22	1.412 (2)
C2—C3	1.388 (2)	C22—C23	1.355 (2)
C3—C4	1.372 (2)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.411 (3)
C4—C5	1.378 (2)	C23—H23	0.9300
C4—H4	0.9300	C24—C27	1.404 (3)
C5—C6	1.392 (2)	C24—C25	1.413 (3)
C5—C8	1.504 (2)	C25—C26	1.355 (2)
C6—C7	1.369 (2)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.418 (3)
C8—H8A	0.9700	C27—C29	1.418 (3)
C8—H8B	0.9700	C30—C32^i	1.345 (2)
C9—C10	1.386 (3)	C30—C31	1.427 (2)
C9—H9	0.9300	C30—H30	0.9300
C10—C11	1.346 (3)	C31—C33	1.385 (2)
C10—H10	0.9300	C31—C32	1.424 (2)
C11—C12	1.398 (3)	C32—C30^i	1.345 (2)
C11—H11	0.9300	C32—H32	0.9300
C12—C13	1.406 (3)	C33—C34	1.421 (3)
C12—C17	1.414 (2)	C33—C35	1.422 (3)
C13—C14	1.339 (3)
C9—N8—C17	121.33 (14)	C15—C16—C17	119.44 (16)
C9—N8—C8	118.82 (15)	C15—C16—H16	120.3
C17—N8—C8	119.84 (14)	C17—C16—H16	120.3
N7—C1—C2	179.0 (2)	N8—C17—C16	122.00 (14)
C7—C2—C3	119.96 (16)	N8—C17—C12	118.08 (16)
C7—C2—C1	120.60 (16)	C16—C17—C12	119.92 (16)
C3—C2—C1	119.39 (17)	N2—C18—C19	178.5 (2)
C4—C3—C2	119.50 (17)	C21—C19—C18	122.40 (16)
C4—C3—H3	120.3	C21—C19—C20	122.78 (17)
C2—C3—H3	120.3	C18—C19—C20	114.76 (15)
C3—C4—C5	120.96 (15)	N1—C20—C19	177.8 (2)
C3—C4—H4	119.5	C19—C21—C26	121.72 (16)
C5—C4—H4	119.5	C19—C21—C22	120.88 (17)
C4—C5—C6	118.98 (16)	C26—C21—C22	117.40 (15)
C4—C5—C8	123.08 (14)	C23—C22—C21	121.42 (18)
C6—C5—C8	117.93 (15)	C23—C22—H22	119.3
C7—C6—C5	120.32 (17)	C21—C22—H22	119.3
C7—C6—H6	119.8	C22—C23—C24	121.26 (17)
C5—C6—H6	119.8	C22—C23—H23	119.4
C6—C7—C2	120.22 (16)	C24—C23—H23	119.4
C6—C7—H7	119.9	C27—C24—C23	121.30 (18)
C2—C7—H7	119.9	C27—C24—C25	121.46 (19)
N8—C8—C5	113.19 (14)	C23—C24—C25	117.23 (16)
N8—C8—H8A	108.9	C26—C25—C24	121.59 (19)
C5—C8—H8A	108.9	C26—C25—H25	119.2
N8—C8—H8B	108.9	C24—C25—H25	119.2
C5—C8—H8B	108.9	C25—C26—C21	121.10 (18)
H8A—C8—H8B	107.8	C25—C26—H26	119.5
N8—C9—C10	121.94 (18)	C21—C26—H26	119.5
N8—C9—H9	119.0	C24—C27—C28	120.9 (2)
C10—C9—H9	119.0	C24—C27—C29	122.11 (19)
C11—C10—C9	119.12 (18)	C28—C27—C29	117.02 (17)
C11—C10—H10	120.4	N3—C28—C27	179.2 (2)
C9—C10—H10	120.4	N4—C29—C27	179.9 (3)
C10—C11—C12	120.51 (16)	C32^i—C30—C31	121.20 (16)
C10—C11—H11	119.7	C32^i—C30—H30	119.4
C12—C11—H11	119.7	C31—C30—H30	119.4
C11—C12—C13	122.90 (17)	C33—C31—C32	121.26 (16)
C11—C12—C17	118.96 (18)	C33—C31—C30	121.30 (16)
C13—C12—C17	118.13 (18)	C32—C31—C30	117.42 (14)
C14—C13—C12	121.09 (17)	C30^i—C32—C31	121.38 (16)
C14—C13—H13	119.5	C30^i—C32—H32	119.3
C12—C13—H13	119.5	C31—C32—H32	119.3
C13—C14—C15	120.14 (19)	C31—C33—C34	121.53 (16)
C13—C14—H14	119.9	C31—C33—C35	122.36 (17)
C15—C14—H14	119.9	C34—C33—C35	116.11 (15)
C16—C15—C14	121.3 (2)	N6—C34—C33	177.8 (2)
C16—C15—H15	119.4	N5—C35—C33	179.3 (2)
C14—C15—H15	119.4
C7—C2—C3—C4	−1.8 (3)	C11—C12—C17—N8	−1.3 (2)
C1—C2—C3—C4	175.76 (16)	C13—C12—C17—N8	179.64 (15)
C2—C3—C4—C5	−0.2 (3)	C11—C12—C17—C16	178.62 (15)
C3—C4—C5—C6	2.0 (3)	C13—C12—C17—C16	−0.5 (2)
C3—C4—C5—C8	−178.58 (17)	C18—C19—C21—C26	−176.51 (19)
C4—C5—C6—C7	−1.9 (3)	C20—C19—C21—C26	0.4 (3)
C8—C5—C6—C7	178.66 (17)	C18—C19—C21—C22	3.2 (3)
C5—C6—C7—C2	0.0 (3)	C20—C19—C21—C22	−179.88 (18)
C3—C2—C7—C6	1.9 (3)	C19—C21—C22—C23	−178.83 (19)
C1—C2—C7—C6	−175.62 (18)	C26—C21—C22—C23	0.9 (3)
C9—N8—C8—C5	−105.13 (18)	C21—C22—C23—C24	−0.7 (3)
C17—N8—C8—C5	73.8 (2)	C22—C23—C24—C27	179.34 (19)
C4—C5—C8—N8	10.8 (2)	C22—C23—C24—C25	0.7 (3)
C6—C5—C8—N8	−169.85 (15)	C27—C24—C25—C26	−179.5 (2)
C17—N8—C9—C10	2.0 (3)	C23—C24—C25—C26	−0.8 (3)
C8—N8—C9—C10	−179.11 (16)	C24—C25—C26—C21	1.0 (3)
N8—C9—C10—C11	−1.3 (3)	C19—C21—C26—C25	178.71 (19)
C9—C10—C11—C12	−0.8 (3)	C22—C21—C26—C25	−1.0 (3)
C10—C11—C12—C13	−178.98 (18)	C23—C24—C27—C28	−0.5 (3)
C10—C11—C12—C17	2.0 (3)	C25—C24—C27—C28	178.10 (19)
C11—C12—C13—C14	−179.31 (19)	C23—C24—C27—C29	179.1 (2)
C17—C12—C13—C14	−0.3 (3)	C25—C24—C27—C29	−2.3 (3)
C12—C13—C14—C15	0.7 (3)	C32^i—C30—C31—C33	178.86 (18)
C13—C14—C15—C16	−0.4 (3)	C32^i—C30—C31—C32	0.5 (3)
C14—C15—C16—C17	−0.4 (3)	C33—C31—C32—C30^i	−178.86 (18)
C9—N8—C17—C16	179.43 (16)	C30—C31—C32—C30^i	−0.5 (3)
C8—N8—C17—C16	0.5 (2)	C32—C31—C33—C34	176.15 (17)
C9—N8—C17—C12	−0.7 (2)	C30—C31—C33—C34	−2.2 (3)
C8—N8—C17—C12	−179.58 (14)	C32—C31—C33—C35	−3.8 (3)
C15—C16—C17—N8	−179.34 (15)	C30—C31—C33—C35	177.91 (17)
C15—C16—C17—C12	0.8 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···N1^ii	0.93	2.58	3.220 (3)	126
C16—H16···N6^iii	0.93	2.46	3.346 (2)	160
C11—H11···N3^i	0.93	2.58	3.426 (3)	151
C4—H4···N8	0.93	2.51	2.856 (2)	102
C3—H3···N7^iv	0.93	2.58	3.435 (3)	154

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