2,2'-(Disulfanedi-yl)bis-[4,6-(4-fluoro-phen-yl)pyrimidine].

The title compound, C(32)H(18)F(4)N(4)S(2), is a disulfide symmetric-ally substituted with two diaza-meta-terphenyl groups. In the crystal, the mol-ecule adopts a twisted conformation with a C-S-S-C torsion angle of -91.82 (7)°. One of the 4,6-(4-fluoro-phen-yl)pyrimidine groups is virtually planar, with dihedral angles between the pyrimidine and benzene groups of 4.00 (8) and 5.44 (8)°, wheares the other is non-planar with analogues dihedral angles of 18.69 (8) and 26.60 (8)°. The planar 4,6-(4-fluoro-phen-yl)pyrimidine groups are involved in π-π stacking inter-actions via their 4-fluoro-phenyl groups [centroid-centroid distances of 3.8556 (11) and 3.9284 (11) Å] that assemble the mol-ecules into columns extended along the a axis. In addition, the structure is stabilized by C-F⋯π [F⋯centroid = 3.4017 (16) Å], C-H⋯F and C-H⋯π inter-actions.

Related literature

For our work on the synthesis of different derivatives of chalcones, see: Samshuddin et al. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶). For the graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). Metrical parameters of similar compounds were retrieved from the Cambridge Structural Database (Allen, 2002 ▶).

Experimental

Crystal data

C32H18F4N4S2

M = 598.62

Triclinic,

a = 9.3371 (2) Å

b = 11.3093 (3) Å

c = 13.1984 (3) Å

α = 102.364 (1)°

β = 93.094 (1)°

γ = 94.010 (1)°

V = 1354.64 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 200 K

0.50 × 0.42 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.899, T max = 1.000

22345 measured reflections

6451 independent reflections

5761 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.08

6451 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001912/gk2426sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812001912/gk2426Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001912/gk2426Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812001912/gk2426Isup4.cml

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

C32H18F4N4S2	Z = 2
Mr = 598.62	F(000) = 612
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Melting point: 473 K
a = 9.3371 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3093 (3) Å	Cell parameters from 9335 reflections
c = 13.1984 (3) Å	θ = 2.7–28.3°
α = 102.364 (1)°	µ = 0.26 mm−1
β = 93.094 (1)°	T = 200 K
γ = 94.010 (1)°	Block, colourless
V = 1354.64 (6) Å3	0.50 × 0.42 × 0.29 mm

Bruker APEXII CCD diffractometer	6451 independent reflections
Radiation source: fine-focus sealed tube	5761 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.899, Tmax = 1.000	k = −14→14
22345 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0346P)2 + 0.9028P] where P = (Fo2 + 2Fc2)/3
6451 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.37731 (5)	0.31376 (4)	0.26342 (3)	0.03759 (11)
S2	0.23667 (4)	0.41454 (4)	0.34681 (3)	0.03494 (10)
F1	−0.06380 (17)	0.81314 (12)	−0.05425 (12)	0.0723 (4)
F2	0.73521 (13)	−0.01865 (10)	−0.30804 (9)	0.0521 (3)
F3	0.02419 (15)	1.00874 (11)	0.83195 (11)	0.0637 (3)
F4	1.10058 (14)	0.77983 (16)	0.33546 (12)	0.0774 (4)
N1	0.29556 (14)	0.44408 (12)	0.12393 (10)	0.0311 (3)
N2	0.44257 (14)	0.27892 (12)	0.07397 (10)	0.0320 (3)
N3	0.26650 (14)	0.61506 (12)	0.48428 (10)	0.0320 (3)
N4	0.47390 (14)	0.57227 (13)	0.38773 (10)	0.0334 (3)
C1	0.36867 (17)	0.35313 (14)	0.13960 (11)	0.0309 (3)
C2	0.29035 (16)	0.46115 (13)	0.02575 (12)	0.0292 (3)
C3	0.36157 (17)	0.38768 (15)	−0.05031 (12)	0.0334 (3)
H3	0.3566	0.3989	−0.1197	0.040*
C4	0.44010 (16)	0.29759 (14)	−0.02361 (11)	0.0294 (3)
C5	0.34108 (16)	0.54935 (14)	0.41297 (11)	0.0308 (3)
C6	0.33586 (17)	0.71875 (14)	0.54009 (12)	0.0318 (3)
C7	0.47672 (17)	0.75261 (15)	0.52079 (12)	0.0349 (3)
H7	0.5264	0.8257	0.5600	0.042*
C8	0.54258 (17)	0.67698 (15)	0.44294 (12)	0.0331 (3)
C11	0.20270 (17)	0.55857 (14)	0.00478 (12)	0.0320 (3)
C12	0.12508 (18)	0.62160 (15)	0.08269 (14)	0.0370 (3)
H12	0.1329	0.6046	0.1501	0.044*
C13	0.0366 (2)	0.70877 (16)	0.06379 (16)	0.0440 (4)
H13	−0.0162	0.7519	0.1173	0.053*
C14	0.0272 (2)	0.73108 (16)	−0.03430 (17)	0.0499 (5)
C15	0.1043 (3)	0.67359 (18)	−0.11258 (16)	0.0552 (5)
H15	0.0969	0.6925	−0.1793	0.066*
C16	0.1936 (2)	0.58729 (17)	−0.09272 (14)	0.0459 (4)
H16	0.2490	0.5473	−0.1460	0.055*
C21	0.52169 (16)	0.21607 (14)	−0.09826 (12)	0.0300 (3)
C22	0.53314 (18)	0.23192 (16)	−0.19960 (13)	0.0371 (3)
H22	0.4902	0.2973	−0.2207	0.045*
C23	0.60651 (18)	0.15328 (17)	−0.26961 (13)	0.0393 (4)
H23	0.6139	0.1637	−0.3387	0.047*
C24	0.66812 (18)	0.06038 (15)	−0.23720 (13)	0.0373 (3)
C25	0.6638 (2)	0.04285 (16)	−0.13765 (14)	0.0425 (4)
H25	0.7102	−0.0212	−0.1170	0.051*
C26	0.58958 (19)	0.12172 (15)	−0.06828 (13)	0.0378 (3)
H26	0.5848	0.1113	0.0010	0.045*
C31	0.25489 (17)	0.79344 (14)	0.61996 (12)	0.0327 (3)
C32	0.10495 (17)	0.77498 (15)	0.61593 (13)	0.0346 (3)
H32	0.0560	0.7119	0.5637	0.042*
C33	0.02688 (19)	0.84753 (16)	0.68718 (14)	0.0393 (4)
H33	−0.0752	0.8360	0.6835	0.047*
C34	0.1000 (2)	0.93649 (16)	0.76335 (15)	0.0435 (4)
C35	0.2474 (2)	0.95525 (17)	0.77240 (17)	0.0512 (5)
H35	0.2954	1.0161	0.8270	0.061*
C36	0.3244 (2)	0.88330 (17)	0.69998 (15)	0.0460 (4)
H36	0.4265	0.8954	0.7049	0.055*
C41	0.69065 (17)	0.70585 (16)	0.41465 (12)	0.0360 (3)
C42	0.7498 (2)	0.82591 (19)	0.43150 (15)	0.0453 (4)
H42	0.6955	0.8905	0.4621	0.054*
C43	0.8882 (2)	0.8507 (2)	0.40345 (16)	0.0530 (5)
H43	0.9290	0.9321	0.4137	0.064*
C44	0.9643 (2)	0.7556 (2)	0.36075 (15)	0.0528 (5)
C45	0.9107 (2)	0.6363 (2)	0.34300 (16)	0.0518 (5)
H45	0.9668	0.5725	0.3134	0.062*
C46	0.77154 (19)	0.61228 (18)	0.36986 (14)	0.0421 (4)
H46	0.7310	0.5306	0.3574	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0500 (2)	0.0384 (2)	0.02800 (19)	0.01296 (17)	0.00568 (16)	0.01157 (15)
S2	0.0364 (2)	0.0365 (2)	0.03120 (19)	−0.00018 (15)	0.00548 (15)	0.00601 (15)
F1	0.0848 (10)	0.0544 (7)	0.0823 (10)	0.0325 (7)	−0.0139 (8)	0.0213 (7)
F2	0.0581 (7)	0.0488 (6)	0.0472 (6)	0.0148 (5)	0.0151 (5)	−0.0004 (5)
F3	0.0668 (8)	0.0465 (7)	0.0701 (8)	0.0144 (6)	0.0177 (6)	−0.0103 (6)
F4	0.0405 (7)	0.1182 (13)	0.0760 (9)	−0.0167 (7)	0.0180 (6)	0.0305 (9)
N1	0.0334 (6)	0.0321 (6)	0.0283 (6)	0.0045 (5)	0.0021 (5)	0.0074 (5)
N2	0.0335 (6)	0.0352 (7)	0.0287 (6)	0.0058 (5)	0.0026 (5)	0.0087 (5)
N3	0.0300 (6)	0.0357 (7)	0.0307 (6)	0.0016 (5)	0.0020 (5)	0.0085 (5)
N4	0.0315 (6)	0.0414 (7)	0.0298 (6)	0.0033 (5)	0.0047 (5)	0.0126 (5)
C1	0.0336 (7)	0.0332 (7)	0.0267 (7)	0.0024 (6)	0.0014 (6)	0.0085 (6)
C2	0.0282 (7)	0.0297 (7)	0.0297 (7)	−0.0012 (5)	−0.0011 (5)	0.0086 (6)
C3	0.0373 (8)	0.0370 (8)	0.0278 (7)	0.0049 (6)	0.0021 (6)	0.0110 (6)
C4	0.0281 (7)	0.0318 (7)	0.0282 (7)	−0.0007 (5)	0.0018 (5)	0.0077 (6)
C5	0.0315 (7)	0.0366 (8)	0.0264 (7)	0.0017 (6)	0.0012 (6)	0.0119 (6)
C6	0.0321 (7)	0.0348 (8)	0.0302 (7)	0.0016 (6)	−0.0001 (6)	0.0115 (6)
C7	0.0336 (8)	0.0393 (8)	0.0321 (8)	−0.0025 (6)	−0.0010 (6)	0.0113 (6)
C8	0.0309 (7)	0.0427 (8)	0.0290 (7)	0.0010 (6)	0.0000 (6)	0.0159 (6)
C11	0.0323 (7)	0.0285 (7)	0.0349 (8)	−0.0006 (6)	−0.0031 (6)	0.0082 (6)
C12	0.0379 (8)	0.0344 (8)	0.0395 (8)	0.0035 (6)	0.0015 (7)	0.0100 (7)
C13	0.0433 (9)	0.0357 (8)	0.0522 (10)	0.0084 (7)	0.0016 (8)	0.0070 (7)
C14	0.0538 (11)	0.0323 (9)	0.0634 (12)	0.0092 (8)	−0.0146 (9)	0.0130 (8)
C15	0.0795 (15)	0.0446 (10)	0.0440 (10)	0.0137 (10)	−0.0101 (10)	0.0165 (8)
C16	0.0620 (12)	0.0413 (9)	0.0364 (9)	0.0113 (8)	0.0000 (8)	0.0117 (7)
C21	0.0273 (7)	0.0323 (7)	0.0291 (7)	−0.0008 (6)	0.0020 (5)	0.0048 (6)
C22	0.0368 (8)	0.0445 (9)	0.0323 (8)	0.0084 (7)	0.0035 (6)	0.0117 (7)
C23	0.0363 (8)	0.0521 (10)	0.0296 (8)	0.0060 (7)	0.0055 (6)	0.0080 (7)
C24	0.0320 (8)	0.0382 (8)	0.0376 (8)	0.0009 (6)	0.0064 (6)	−0.0010 (7)
C25	0.0489 (10)	0.0362 (8)	0.0443 (9)	0.0113 (7)	0.0067 (8)	0.0095 (7)
C26	0.0438 (9)	0.0376 (8)	0.0341 (8)	0.0058 (7)	0.0057 (7)	0.0106 (7)
C31	0.0340 (8)	0.0318 (7)	0.0330 (8)	0.0026 (6)	0.0017 (6)	0.0083 (6)
C32	0.0344 (8)	0.0355 (8)	0.0335 (8)	0.0019 (6)	0.0001 (6)	0.0074 (6)
C33	0.0369 (8)	0.0378 (8)	0.0441 (9)	0.0063 (7)	0.0058 (7)	0.0096 (7)
C34	0.0531 (10)	0.0313 (8)	0.0460 (10)	0.0104 (7)	0.0092 (8)	0.0046 (7)
C35	0.0538 (11)	0.0379 (9)	0.0529 (11)	0.0000 (8)	−0.0012 (9)	−0.0077 (8)
C36	0.0384 (9)	0.0421 (9)	0.0515 (11)	−0.0013 (7)	−0.0011 (8)	−0.0004 (8)
C41	0.0311 (7)	0.0506 (9)	0.0291 (7)	−0.0020 (7)	0.0003 (6)	0.0171 (7)
C42	0.0414 (9)	0.0535 (11)	0.0431 (9)	−0.0045 (8)	0.0022 (7)	0.0183 (8)
C43	0.0474 (10)	0.0652 (13)	0.0479 (11)	−0.0160 (9)	−0.0002 (8)	0.0233 (9)
C44	0.0336 (9)	0.0871 (15)	0.0401 (10)	−0.0092 (9)	0.0050 (7)	0.0229 (10)
C45	0.0390 (9)	0.0746 (14)	0.0452 (10)	0.0052 (9)	0.0113 (8)	0.0184 (10)
C46	0.0360 (8)	0.0555 (10)	0.0373 (9)	0.0002 (7)	0.0069 (7)	0.0161 (8)

S1—C1	1.7827 (15)	C15—H15	0.9500
S1—S2	2.0156 (6)	C16—H16	0.9500
S2—C5	1.7798 (16)	C21—C26	1.395 (2)
F1—C14	1.357 (2)	C21—C22	1.396 (2)
F2—C24	1.3598 (18)	C22—C23	1.384 (2)
F3—C34	1.350 (2)	C22—H22	0.9500
F4—C44	1.357 (2)	C23—C24	1.367 (3)
N1—C1	1.319 (2)	C23—H23	0.9500
N1—C2	1.3492 (19)	C24—C25	1.372 (3)
N2—C1	1.329 (2)	C25—C26	1.386 (2)
N2—C4	1.3482 (19)	C25—H25	0.9500
N3—C5	1.329 (2)	C26—H26	0.9500
N3—C6	1.345 (2)	C31—C36	1.394 (2)
N4—C5	1.324 (2)	C31—C32	1.397 (2)
N4—C8	1.349 (2)	C32—C33	1.384 (2)
C2—C3	1.390 (2)	C32—H32	0.9500
C2—C11	1.481 (2)	C33—C34	1.373 (3)
C3—C4	1.389 (2)	C33—H33	0.9500
C3—H3	0.9500	C34—C35	1.373 (3)
C4—C21	1.480 (2)	C35—C36	1.384 (3)
C6—C7	1.396 (2)	C35—H35	0.9500
C6—C31	1.480 (2)	C36—H36	0.9500
C7—C8	1.389 (2)	C41—C46	1.390 (3)
C7—H7	0.9500	C41—C42	1.397 (3)
C8—C41	1.484 (2)	C42—C43	1.389 (3)
C11—C12	1.389 (2)	C42—H42	0.9500
C11—C16	1.393 (2)	C43—C44	1.368 (3)
C12—C13	1.383 (2)	C43—H43	0.9500
C12—H12	0.9500	C44—C45	1.372 (3)
C13—C14	1.371 (3)	C45—C46	1.389 (2)
C13—H13	0.9500	C45—H45	0.9500
C14—C15	1.367 (3)	C46—H46	0.9500
C15—C16	1.384 (3)
C1—S1—S2	105.41 (5)	C23—C22—C21	120.60 (16)
C5—S2—S1	104.74 (6)	C23—C22—H22	119.7
C1—N1—C2	115.20 (13)	C21—C22—H22	119.7
C1—N2—C4	115.30 (13)	C24—C23—C22	118.61 (15)
C5—N3—C6	115.81 (13)	C24—C23—H23	120.7
C5—N4—C8	114.91 (14)	C22—C23—H23	120.7
N1—C1—N2	129.52 (14)	F2—C24—C23	117.82 (15)
N1—C1—S1	120.58 (12)	F2—C24—C25	119.01 (16)
N2—C1—S1	109.89 (11)	C23—C24—C25	123.17 (15)
N1—C2—C3	120.47 (14)	C24—C25—C26	117.77 (16)
N1—C2—C11	116.29 (13)	C24—C25—H25	121.1
C3—C2—C11	123.22 (14)	C26—C25—H25	121.1
C4—C3—C2	119.16 (14)	C25—C26—C21	121.27 (15)
C4—C3—H3	120.4	C25—C26—H26	119.4
C2—C3—H3	120.4	C21—C26—H26	119.4
N2—C4—C3	120.26 (14)	C36—C31—C32	118.43 (15)
N2—C4—C21	116.35 (13)	C36—C31—C6	121.64 (15)
C3—C4—C21	123.37 (13)	C32—C31—C6	119.93 (14)
N4—C5—N3	129.16 (15)	C33—C32—C31	120.76 (15)
N4—C5—S2	120.13 (12)	C33—C32—H32	119.6
N3—C5—S2	110.71 (11)	C31—C32—H32	119.6
N3—C6—C7	120.32 (15)	C34—C33—C32	118.64 (16)
N3—C6—C31	116.76 (14)	C34—C33—H33	120.7
C7—C6—C31	122.91 (14)	C32—C33—H33	120.7
C8—C7—C6	118.45 (15)	F3—C34—C35	118.55 (17)
C8—C7—H7	120.8	F3—C34—C33	118.85 (17)
C6—C7—H7	120.8	C35—C34—C33	122.60 (17)
N4—C8—C7	121.34 (14)	C34—C35—C36	118.30 (17)
N4—C8—C41	115.90 (15)	C34—C35—H35	120.8
C7—C8—C41	122.76 (15)	C36—C35—H35	120.8
C12—C11—C16	118.72 (15)	C35—C36—C31	121.21 (17)
C12—C11—C2	119.89 (14)	C35—C36—H36	119.4
C16—C11—C2	121.37 (15)	C31—C36—H36	119.4
C13—C12—C11	121.13 (16)	C46—C41—C42	119.34 (16)
C13—C12—H12	119.4	C46—C41—C8	119.66 (16)
C11—C12—H12	119.4	C42—C41—C8	121.00 (16)
C14—C13—C12	118.09 (18)	C43—C42—C41	120.0 (2)
C14—C13—H13	121.0	C43—C42—H42	120.0
C12—C13—H13	121.0	C41—C42—H42	120.0
F1—C14—C15	118.92 (19)	C44—C43—C42	118.61 (19)
F1—C14—C13	118.28 (19)	C44—C43—H43	120.7
C15—C14—C13	122.80 (17)	C42—C43—H43	120.7
C14—C15—C16	118.70 (18)	F4—C44—C43	118.6 (2)
C14—C15—H15	120.7	F4—C44—C45	118.0 (2)
C16—C15—H15	120.7	C43—C44—C45	123.44 (18)
C15—C16—C11	120.50 (18)	C44—C45—C46	117.6 (2)
C15—C16—H16	119.8	C44—C45—H45	121.2
C11—C16—H16	119.8	C46—C45—H45	121.2
C26—C21—C22	118.54 (15)	C45—C46—C41	121.01 (18)
C26—C21—C4	120.41 (14)	C45—C46—H46	119.5
C22—C21—C4	121.05 (14)	C41—C46—H46	119.5
C1—S1—S2—C5	−91.82 (7)	N2—C4—C21—C26	3.4 (2)
C2—N1—C1—N2	2.9 (2)	C3—C4—C21—C26	−175.27 (15)
C2—N1—C1—S1	−176.59 (11)	N2—C4—C21—C22	−176.28 (14)
C4—N2—C1—N1	−1.5 (2)	C3—C4—C21—C22	5.1 (2)
C4—N2—C1—S1	178.03 (11)	C26—C21—C22—C23	2.0 (2)
S2—S1—C1—N1	8.39 (14)	C4—C21—C22—C23	−178.31 (15)
S2—S1—C1—N2	−171.23 (10)	C21—C22—C23—C24	−0.4 (3)
C1—N1—C2—C3	−1.5 (2)	C22—C23—C24—F2	177.63 (15)
C1—N1—C2—C11	176.95 (13)	C22—C23—C24—C25	−1.6 (3)
N1—C2—C3—C4	−1.0 (2)	F2—C24—C25—C26	−177.34 (15)
C11—C2—C3—C4	−179.30 (14)	C23—C24—C25—C26	1.9 (3)
C1—N2—C4—C3	−1.3 (2)	C24—C25—C26—C21	−0.2 (3)
C1—N2—C4—C21	179.99 (13)	C22—C21—C26—C25	−1.7 (3)
C2—C3—C4—N2	2.5 (2)	C4—C21—C26—C25	178.59 (15)
C2—C3—C4—C21	−178.93 (14)	N3—C6—C31—C36	162.50 (16)
C8—N4—C5—N3	0.4 (2)	C7—C6—C31—C36	−18.4 (2)
C8—N4—C5—S2	179.94 (11)	N3—C6—C31—C32	−17.8 (2)
C6—N3—C5—N4	−1.1 (2)	C7—C6—C31—C32	161.33 (15)
C6—N3—C5—S2	179.26 (11)	C36—C31—C32—C33	2.6 (2)
S1—S2—C5—N4	10.80 (13)	C6—C31—C32—C33	−177.10 (15)
S1—S2—C5—N3	−169.55 (9)	C31—C32—C33—C34	−1.3 (3)
C5—N3—C6—C7	0.8 (2)	C32—C33—C34—F3	178.93 (16)
C5—N3—C6—C31	179.98 (13)	C32—C33—C34—C35	−0.9 (3)
N3—C6—C7—C8	0.1 (2)	F3—C34—C35—C36	−178.10 (18)
C31—C6—C7—C8	−179.02 (14)	C33—C34—C35—C36	1.7 (3)
C5—N4—C8—C7	0.7 (2)	C34—C35—C36—C31	−0.3 (3)
C5—N4—C8—C41	−178.85 (13)	C32—C31—C36—C35	−1.8 (3)
C6—C7—C8—N4	−0.9 (2)	C6—C31—C36—C35	177.95 (17)
C6—C7—C8—C41	178.62 (14)	N4—C8—C41—C46	−26.2 (2)
N1—C2—C11—C12	−3.7 (2)	C7—C8—C41—C46	154.22 (16)
C3—C2—C11—C12	174.69 (15)	N4—C8—C41—C42	153.20 (15)
N1—C2—C11—C16	177.69 (15)	C7—C8—C41—C42	−26.3 (2)
C3—C2—C11—C16	−3.9 (2)	C46—C41—C42—C43	0.1 (3)
C16—C11—C12—C13	2.0 (3)	C8—C41—C42—C43	−179.39 (16)
C2—C11—C12—C13	−176.68 (15)	C41—C42—C43—C44	−0.8 (3)
C11—C12—C13—C14	0.2 (3)	C42—C43—C44—F4	−178.60 (17)
C12—C13—C14—F1	177.49 (17)	C42—C43—C44—C45	0.7 (3)
C12—C13—C14—C15	−1.9 (3)	F4—C44—C45—C46	179.51 (17)
F1—C14—C15—C16	−178.03 (19)	C43—C44—C45—C46	0.2 (3)
C13—C14—C15—C16	1.4 (3)	C44—C45—C46—C41	−1.0 (3)
C14—C15—C16—C11	0.9 (3)	C42—C41—C46—C45	0.9 (3)
C12—C11—C16—C15	−2.5 (3)	C8—C41—C46—C45	−179.67 (16)
C2—C11—C16—C15	176.11 (17)

Cg2 and Cg5 are the centroids of the N3/N4/C5–C8 and C31–C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···F2i	0.95	2.49	3.204 (2)	132
C15—H15···Cg5ii	0.95	2.92	3.751 (2)	147
C23—H23···Cg2iii	0.95	2.98	3.7690 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg5 are the centroids of the N3/N4/C5–C8 and C31–C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯F2i	0.95	2.49	3.204 (2)	132
C15—H15⋯Cg5ii	0.95	2.92	3.751 (2)	147
C23—H23⋯Cg2iii	0.95	2.98	3.7690 (19)	141

Symmetry codes: (i) ; (ii) ; (iii) .