1,2,7,8-Tetra­methyl-4,5-dihydro-3a,5a-diaza­pyrene ditriflate

Coe, B.J.; Fitzgerald, E.C.; Raftery, J.

doi:10.1107/S1600536806035379

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 10| October 2006| Pages o4335-o4336

https://doi.org/10.1107/S1600536806035379

1,2,7,8-Tetramethyl-4,5-dihydro-3a,5a-diazapyrene ditriflate

Benjamin J. Coe,^a ^* Emma C. Fitzgerald ^a and James Raftery ^a

^aSchool of Chemistry, University of Manchester, Manchester M13 9PL, England
^*Correspondence e-mail: b.coe@manchester.ac.uk

(Received 23 August 2006; accepted 1 September 2006; online 8 September 2006)

The title structure, C₁₈H₂₀N₂²⁺·2CF₃O₃S⁻, is the first to be reported for a diquaternized derivative of 3,4,7,8-tetramethyl-1,10-phenanthroline.

Comment

Relevant background information on this work and comments on the title structure, (II), together with that of the closely related salt 3,6-dimethyl-4,5-dihydro-3a,5a-diazapyrene ditriflate, (I), can be found in the preceding paper (Coe, Fitzgerald & Raftery, 2006 ). The molecular structure of (II) is shown in Fig. 1 and selected geometric parameters are given in Table 1.

Figure 1
The asymmetric unit of (II)

, showing 50% probability displacement ellipsoids.

Experimental

Salt (II) was synthesized as reported previously (Coe, Curati & Fitzgerald, 2006 ). Crystals suitable for single-crystal X-ray diffraction were obtained by slow diffusion of diethyl ether vapour into an acetone solution of (II) at 295 K.

Crystal data

C₁₈H₂₀N₂²⁺·2CF₃O₃S⁻
M_r = 562.50
Monoclinic, P 2₁ /c
a = 12.882 (1) Å
b = 8.152 (1) Å
c = 22.585 (1) Å
β = 104.284 (1)°
V = 2298.4 (2) Å³
Z = 4
D_x = 1.626 Mg m⁻³
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 (2) K
Block, white
0.45 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
φ and ω scans
Absorption correction: none
19382 measured reflections
5467 independent reflections
4426 reflections with I > 2σ(I)
R_int = 0.058
θ_max = 28.3°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.08
5467 reflections
329 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0667P)² + 1.2422P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—N1	1.364 (2)
C1—C9	1.404 (3)
C1—C2	1.433 (3)
C2—N2	1.369 (2)
C2—C6	1.399 (3)
C3—N2	1.330 (2)
C3—C4	1.393 (3)
C4—C5	1.385 (3)
C4—C15	1.505 (3)
C5—C6	1.430 (3)
C5—C16	1.501 (3)
C6—C7	1.435 (3)
C7—C8	1.355 (3)
C8—C9	1.434 (3)
C9—C10	1.427 (3)
C10—C11	1.388 (3)
C10—C17	1.501 (3)
C11—C12	1.395 (3)
C11—C18	1.503 (3)
C12—N1	1.329 (2)
C13—N1	1.483 (2)
C13—C14	1.504 (3)
C14—N2	1.479 (2)

N1—C1—C2	119.87 (17)
N2—C2—C1	119.65 (17)
N1—C13—C14	108.40 (15)
N2—C14—C13	108.35 (15)
C1—N1—C13	118.55 (15)
C2—N2—C14	117.71 (15)

N1—C13—C14—N2	−58.83 (19)

All H atoms were included in calculated positions, with C—H = 0.95 (CH), 0.99 (CH₂) and 0.98 Å (CH₃); U_iso(H) values were fixed at 1.2U_eq(C) or 1.5U_eq(methyl C).

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: SHELXTL (Bruker, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks II, global. DOI: https://doi.org/10.1107/S1600536806035379/lh2168sup1.cif

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S1600536806035379/lh2168IIsup2.hkl

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1,2,7,8-Tetramethyl-4,5-dihydro-3a,5a-diazapyrene ditriflate top

Crystal data top

C₁₈H₂₀N₂²⁺·2CF₃O₃S⁻	F(000) = 1152
M_r = 562.50	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7763 reflections
a = 12.8820 (7) Å	θ = 2.8–28.2°
b = 8.1520 (4) Å	µ = 0.32 mm⁻¹
c = 22.5850 (12) Å	T = 100 K
β = 104.284 (1)°	Plate, white
V = 2298.4 (2) Å³	0.45 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4426 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 28.3°, θ_min = 1.6°
φ and ω scans	h = −17→17
19382 measured reflections	k = −10→10
5467 independent reflections	l = −29→28

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0667P)² + 1.2422P] where P = (F_o² + 2F_c²)/3
5467 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.67 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.

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

	x	y	z	U_iso*/U_eq
C1	0.08483 (15)	0.0957 (2)	0.11781 (9)	0.0156 (4)
C2	−0.02962 (15)	0.1074 (2)	0.09903 (9)	0.0156 (4)
C3	−0.19641 (15)	0.0541 (2)	0.12015 (9)	0.0176 (4)
H3	−0.2360	0.0051	0.1458	0.021*
C4	−0.25087 (15)	0.1421 (2)	0.06899 (9)	0.0177 (4)
C5	−0.19378 (16)	0.2071 (2)	0.03000 (9)	0.0196 (4)
C6	−0.07995 (15)	0.1883 (2)	0.04492 (9)	0.0175 (4)
C7	−0.01382 (16)	0.2462 (3)	0.00665 (9)	0.0214 (4)
H7	−0.0461	0.3025	−0.0301	0.026*
C8	0.09358 (16)	0.2223 (3)	0.02173 (9)	0.0211 (4)
H8	0.1342	0.2561	−0.0060	0.025*
C9	0.14745 (15)	0.1474 (2)	0.07845 (9)	0.0172 (4)
C10	0.26105 (15)	0.1317 (2)	0.09824 (9)	0.0190 (4)
C11	0.30618 (15)	0.0739 (2)	0.15676 (9)	0.0195 (4)
C12	0.23917 (15)	0.0322 (2)	0.19440 (9)	0.0184 (4)
H12	0.2701	−0.0045	0.2348	0.022*
C13	0.06579 (15)	0.0115 (2)	0.21866 (9)	0.0168 (4)
H13A	0.0487	0.1164	0.2362	0.020*
H13B	0.1047	−0.0594	0.2525	0.020*
C14	−0.03566 (15)	−0.0715 (2)	0.18461 (9)	0.0165 (4)
H14A	−0.0187	−0.1781	0.1682	0.020*
H14B	−0.0827	−0.0921	0.2125	0.020*
C15	−0.37036 (15)	0.1594 (3)	0.05822 (10)	0.0217 (4)
H15A	−0.3905	0.2748	0.0504	0.032*
H15B	−0.3926	0.1216	0.0944	0.032*
H15C	−0.4059	0.0930	0.0228	0.032*
C16	−0.25076 (18)	0.2982 (3)	−0.02644 (10)	0.0299 (5)
H16A	−0.3246	0.2584	−0.0399	0.045*
H16B	−0.2137	0.2798	−0.0589	0.045*
H16C	−0.2511	0.4157	−0.0174	0.045*
C17	0.33141 (17)	0.1812 (3)	0.05728 (10)	0.0259 (5)
H17A	0.3547	0.2951	0.0659	0.039*
H17B	0.2912	0.1716	0.0145	0.039*
H17C	0.3943	0.1093	0.0647	0.039*
C18	0.42501 (16)	0.0582 (3)	0.18268 (10)	0.0256 (5)
H18A	0.4543	−0.0210	0.1584	0.038*
H18B	0.4391	0.0201	0.2251	0.038*
H18C	0.4591	0.1652	0.1814	0.038*
C19	0.29745 (17)	0.5445 (3)	0.19959 (11)	0.0245 (4)
C20	0.41878 (19)	0.1440 (3)	0.39136 (12)	0.0326 (5)
F1	0.33941 (11)	0.45210 (19)	0.24792 (8)	0.0426 (4)
F2	0.32142 (11)	0.47396 (18)	0.15109 (7)	0.0379 (4)
F3	0.34766 (11)	0.68971 (17)	0.20785 (7)	0.0354 (3)
F4	0.46066 (15)	0.1354 (3)	0.34373 (11)	0.0848 (8)
F5	0.43790 (12)	0.29605 (19)	0.41287 (8)	0.0491 (4)
F6	0.47371 (16)	0.0461 (2)	0.43370 (12)	0.0923 (9)
N1	0.13323 (13)	0.0425 (2)	0.17525 (7)	0.0153 (3)
N2	−0.09044 (12)	0.0369 (2)	0.13402 (7)	0.0152 (3)
O1	0.14522 (12)	0.65279 (18)	0.24348 (6)	0.0224 (3)
O2	0.11371 (12)	0.40314 (18)	0.18258 (7)	0.0243 (3)
O3	0.12341 (12)	0.6681 (2)	0.13390 (7)	0.0257 (3)
O4	0.2466 (2)	0.1162 (5)	0.42530 (11)	0.1106 (14)
O5	0.27358 (16)	−0.0663 (2)	0.34630 (9)	0.0495 (6)
O6	0.23670 (15)	0.2165 (2)	0.32313 (9)	0.0448 (5)
S1	0.15330 (4)	0.56891 (6)	0.18837 (2)	0.01698 (13)
S2	0.27643 (4)	0.09789 (8)	0.36958 (2)	0.02868 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0166 (9)	0.0146 (9)	0.0145 (9)	0.0008 (7)	0.0016 (7)	−0.0027 (7)
C2	0.0157 (9)	0.0156 (9)	0.0151 (9)	−0.0002 (7)	0.0034 (7)	−0.0022 (7)
C3	0.0153 (9)	0.0189 (9)	0.0186 (9)	−0.0006 (7)	0.0040 (7)	−0.0029 (7)
C4	0.0158 (9)	0.0171 (9)	0.0191 (9)	0.0015 (7)	0.0018 (7)	−0.0040 (7)
C5	0.0179 (9)	0.0213 (10)	0.0175 (9)	0.0030 (7)	0.0006 (7)	0.0000 (8)
C6	0.0171 (9)	0.0184 (9)	0.0164 (9)	0.0011 (7)	0.0028 (7)	−0.0008 (7)
C7	0.0223 (10)	0.0258 (11)	0.0151 (9)	0.0011 (8)	0.0030 (8)	0.0028 (8)
C8	0.0201 (10)	0.0266 (11)	0.0170 (9)	−0.0018 (8)	0.0055 (7)	−0.0002 (8)
C9	0.0157 (9)	0.0186 (9)	0.0168 (9)	−0.0004 (7)	0.0028 (7)	−0.0028 (7)
C10	0.0163 (9)	0.0196 (10)	0.0212 (10)	−0.0006 (7)	0.0049 (7)	−0.0051 (8)
C11	0.0152 (9)	0.0198 (10)	0.0222 (10)	0.0004 (7)	0.0020 (7)	−0.0048 (8)
C12	0.0166 (9)	0.0171 (9)	0.0191 (9)	0.0016 (7)	−0.0002 (7)	−0.0021 (7)
C13	0.0176 (9)	0.0193 (9)	0.0135 (9)	0.0005 (7)	0.0034 (7)	0.0000 (7)
C14	0.0164 (9)	0.0165 (9)	0.0154 (9)	0.0010 (7)	0.0019 (7)	0.0023 (7)
C15	0.0156 (9)	0.0247 (10)	0.0239 (10)	0.0016 (8)	0.0036 (8)	−0.0004 (8)
C16	0.0217 (11)	0.0397 (14)	0.0264 (11)	0.0060 (9)	0.0023 (9)	0.0119 (10)
C17	0.0186 (10)	0.0363 (13)	0.0240 (11)	−0.0016 (9)	0.0073 (8)	−0.0023 (9)
C18	0.0151 (10)	0.0341 (12)	0.0260 (11)	0.0015 (8)	0.0018 (8)	−0.0005 (9)
C19	0.0192 (10)	0.0205 (10)	0.0339 (12)	0.0005 (8)	0.0070 (9)	0.0026 (9)
C20	0.0246 (11)	0.0269 (12)	0.0411 (14)	−0.0015 (9)	−0.0016 (10)	0.0042 (10)
F1	0.0236 (7)	0.0438 (9)	0.0533 (10)	0.0043 (6)	−0.0037 (6)	0.0211 (7)
F2	0.0319 (7)	0.0327 (8)	0.0566 (10)	0.0036 (6)	0.0251 (7)	−0.0068 (7)
F3	0.0248 (7)	0.0250 (7)	0.0571 (9)	−0.0071 (5)	0.0116 (6)	−0.0029 (6)
F4	0.0396 (10)	0.127 (2)	0.0984 (17)	−0.0115 (12)	0.0374 (11)	−0.0415 (16)
F5	0.0384 (9)	0.0333 (8)	0.0651 (11)	−0.0111 (7)	−0.0075 (8)	−0.0052 (8)
F6	0.0620 (12)	0.0471 (11)	0.1228 (19)	−0.0214 (9)	−0.0630 (13)	0.0411 (12)
N1	0.0152 (8)	0.0154 (8)	0.0144 (8)	0.0002 (6)	0.0020 (6)	−0.0013 (6)
N2	0.0150 (8)	0.0155 (8)	0.0145 (8)	0.0006 (6)	0.0024 (6)	−0.0006 (6)
O1	0.0299 (8)	0.0199 (7)	0.0184 (7)	−0.0013 (6)	0.0078 (6)	−0.0024 (6)
O2	0.0233 (8)	0.0209 (8)	0.0288 (8)	−0.0034 (6)	0.0065 (6)	−0.0061 (6)
O3	0.0264 (8)	0.0315 (8)	0.0190 (7)	0.0069 (6)	0.0051 (6)	0.0044 (6)
O4	0.0672 (17)	0.236 (4)	0.0405 (13)	−0.080 (2)	0.0354 (12)	−0.0597 (19)
O5	0.0530 (12)	0.0271 (9)	0.0497 (12)	−0.0114 (8)	−0.0231 (9)	0.0104 (8)
O6	0.0371 (10)	0.0260 (9)	0.0555 (12)	0.0093 (7)	−0.0188 (9)	−0.0055 (8)
S1	0.0166 (2)	0.0177 (2)	0.0162 (2)	0.00113 (17)	0.00335 (17)	−0.00091 (18)
S2	0.0228 (3)	0.0432 (4)	0.0186 (3)	−0.0093 (2)	0.0025 (2)	−0.0046 (2)

Geometric parameters (Å, º) top

C1—N1	1.364 (2)	C14—H14A	0.9900
C1—C9	1.404 (3)	C14—H14B	0.9900
C1—C2	1.433 (3)	C15—H15A	0.9800
C2—N2	1.369 (2)	C15—H15B	0.9800
C2—C6	1.399 (3)	C15—H15C	0.9800
C3—N2	1.330 (2)	C16—H16A	0.9800
C3—C4	1.393 (3)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C4—C5	1.385 (3)	C17—H17A	0.9800
C4—C15	1.505 (3)	C17—H17B	0.9800
C5—C6	1.430 (3)	C17—H17C	0.9800
C5—C16	1.501 (3)	C18—H18A	0.9800
C6—C7	1.435 (3)	C18—H18B	0.9800
C7—C8	1.355 (3)	C18—H18C	0.9800
C7—H7	0.9500	C19—F1	1.326 (3)
C8—C9	1.434 (3)	C19—F2	1.339 (3)
C8—H8	0.9500	C19—F3	1.340 (2)
C9—C10	1.427 (3)	C19—S1	1.822 (2)
C10—C11	1.388 (3)	C20—F6	1.311 (3)
C10—C17	1.501 (3)	C20—F4	1.319 (3)
C11—C12	1.395 (3)	C20—F5	1.332 (3)
C11—C18	1.503 (3)	C20—S2	1.817 (2)
C12—N1	1.329 (2)	O1—S1	1.4461 (15)
C12—H12	0.9500	O2—S1	1.4389 (15)
C13—N1	1.483 (2)	O3—S1	1.4430 (15)
C13—C14	1.504 (3)	O4—S2	1.411 (2)
C13—H13A	0.9900	O5—S2	1.435 (2)
C13—H13B	0.9900	O6—S2	1.4257 (19)
C14—N2	1.479 (2)

N1—C1—C9	119.88 (17)	C4—C15—H15C	109.5
N1—C1—C2	119.87 (17)	H15A—C15—H15C	109.5
C9—C1—C2	120.15 (17)	H15B—C15—H15C	109.5
N2—C2—C6	119.61 (17)	C5—C16—H16A	109.5
N2—C2—C1	119.65 (17)	C5—C16—H16B	109.5
C6—C2—C1	120.73 (17)	H16A—C16—H16B	109.5
N2—C3—C4	121.80 (18)	C5—C16—H16C	109.5
N2—C3—H3	119.1	H16A—C16—H16C	109.5
C4—C3—H3	119.1	H16B—C16—H16C	109.5
C5—C4—C3	119.13 (17)	C10—C17—H17A	109.5
C5—C4—C15	122.96 (18)	C10—C17—H17B	109.5
C3—C4—C15	117.90 (18)	H17A—C17—H17B	109.5
C4—C5—C6	118.93 (17)	C10—C17—H17C	109.5
C4—C5—C16	120.29 (18)	H17A—C17—H17C	109.5
C6—C5—C16	120.77 (18)	H17B—C17—H17C	109.5
C2—C6—C5	118.95 (18)	C11—C18—H18A	109.5
C2—C6—C7	117.71 (17)	C11—C18—H18B	109.5
C5—C6—C7	123.34 (18)	H18A—C18—H18B	109.5
C8—C7—C6	121.52 (18)	C11—C18—H18C	109.5
C8—C7—H7	119.2	H18A—C18—H18C	109.5
C6—C7—H7	119.2	H18B—C18—H18C	109.5
C7—C8—C9	121.64 (18)	F1—C19—F2	107.46 (18)
C7—C8—H8	119.2	F1—C19—F3	107.60 (18)
C9—C8—H8	119.2	F2—C19—F3	107.00 (17)
C1—C9—C10	118.68 (17)	F1—C19—S1	111.77 (15)
C1—C9—C8	117.79 (17)	F2—C19—S1	111.47 (15)
C10—C9—C8	123.43 (18)	F3—C19—S1	111.30 (14)
C11—C10—C9	119.01 (18)	F6—C20—F4	107.9 (3)
C11—C10—C17	120.21 (18)	F6—C20—F5	106.4 (2)
C9—C10—C17	120.76 (18)	F4—C20—F5	105.7 (2)
C10—C11—C12	119.09 (18)	F6—C20—S2	113.50 (18)
C10—C11—C18	123.14 (19)	F4—C20—S2	110.91 (18)
C12—C11—C18	117.75 (18)	F5—C20—S2	112.01 (17)
N1—C12—C11	121.79 (18)	C12—N1—C1	121.42 (17)
N1—C12—H12	119.1	C12—N1—C13	119.76 (16)
C11—C12—H12	119.1	C1—N1—C13	118.55 (15)
N1—C13—C14	108.40 (15)	C3—N2—C2	121.33 (16)
N1—C13—H13A	110.0	C3—N2—C14	120.74 (16)
C14—C13—H13A	110.0	C2—N2—C14	117.71 (15)
N1—C13—H13B	110.0	O2—S1—O3	115.78 (9)
C14—C13—H13B	110.0	O2—S1—O1	115.03 (9)
H13A—C13—H13B	108.4	O3—S1—O1	114.08 (9)
N2—C14—C13	108.35 (15)	O2—S1—C19	103.66 (9)
N2—C14—H14A	110.0	O3—S1—C19	103.20 (10)
C13—C14—H14A	110.0	O1—S1—C19	102.66 (10)
N2—C14—H14B	110.0	O4—S2—O6	117.2 (2)
C13—C14—H14B	110.0	O4—S2—O5	115.9 (2)
H14A—C14—H14B	108.4	O6—S2—O5	113.02 (11)
C4—C15—H15A	109.5	O4—S2—C20	102.44 (13)
C4—C15—H15B	109.5	O6—S2—C20	102.36 (12)
H15A—C15—H15B	109.5	O5—S2—C20	103.00 (12)

N1—C1—C2—N2	−12.2 (3)	C18—C11—C12—N1	179.98 (18)
C9—C1—C2—N2	171.28 (17)	N1—C13—C14—N2	−58.83 (19)
N1—C1—C2—C6	168.58 (17)	C11—C12—N1—C1	−0.5 (3)
C9—C1—C2—C6	−7.9 (3)	C11—C12—N1—C13	−174.41 (17)
N2—C3—C4—C5	2.9 (3)	C9—C1—N1—C12	−2.6 (3)
N2—C3—C4—C15	−178.04 (18)	C2—C1—N1—C12	−179.12 (17)
C3—C4—C5—C6	−2.7 (3)	C9—C1—N1—C13	171.34 (17)
C15—C4—C5—C6	178.30 (18)	C2—C1—N1—C13	−5.2 (3)
C3—C4—C5—C16	178.20 (19)	C14—C13—N1—C12	−145.00 (17)
C15—C4—C5—C16	−0.8 (3)	C14—C13—N1—C1	40.9 (2)
N2—C2—C6—C5	5.1 (3)	C4—C3—N2—C2	1.1 (3)
C1—C2—C6—C5	−175.67 (17)	C4—C3—N2—C14	−173.38 (17)
N2—C2—C6—C7	−173.98 (18)	C6—C2—N2—C3	−5.1 (3)
C1—C2—C6—C7	5.2 (3)	C1—C2—N2—C3	175.66 (17)
C4—C5—C6—C2	−1.2 (3)	C6—C2—N2—C14	169.46 (17)
C16—C5—C6—C2	177.84 (19)	C1—C2—N2—C14	−9.7 (2)
C4—C5—C6—C7	177.84 (19)	C13—C14—N2—C3	−139.88 (18)
C16—C5—C6—C7	−3.1 (3)	C13—C14—N2—C2	45.5 (2)
C2—C6—C7—C8	0.7 (3)	F1—C19—S1—O2	−57.66 (18)
C5—C6—C7—C8	−178.4 (2)	F2—C19—S1—O2	62.62 (17)
C6—C7—C8—C9	−4.0 (3)	F3—C19—S1—O2	−178.00 (15)
N1—C1—C9—C10	4.4 (3)	F1—C19—S1—O3	−178.78 (16)
C2—C1—C9—C10	−179.06 (17)	F2—C19—S1—O3	−58.49 (17)
N1—C1—C9—C8	−171.96 (17)	F3—C19—S1—O3	60.88 (18)
C2—C1—C9—C8	4.5 (3)	F1—C19—S1—O1	62.40 (17)
C7—C8—C9—C1	1.3 (3)	F2—C19—S1—O1	−177.32 (14)
C7—C8—C9—C10	−174.9 (2)	F3—C19—S1—O1	−57.94 (18)
C1—C9—C10—C11	−3.3 (3)	F6—C20—S2—O4	59.4 (3)
C8—C9—C10—C11	172.95 (19)	F4—C20—S2—O4	−178.9 (3)
C1—C9—C10—C17	178.44 (18)	F5—C20—S2—O4	−61.1 (3)
C8—C9—C10—C17	−5.4 (3)	F6—C20—S2—O6	−178.7 (2)
C9—C10—C11—C12	0.3 (3)	F4—C20—S2—O6	−57.1 (2)
C17—C10—C11—C12	178.57 (19)	F5—C20—S2—O6	60.7 (2)
C9—C10—C11—C18	−177.92 (19)	F6—C20—S2—O5	−61.2 (2)
C17—C10—C11—C18	0.4 (3)	F4—C20—S2—O5	60.4 (2)
C10—C11—C12—N1	1.7 (3)	F5—C20—S2—O5	178.22 (18)

Acknowledgements

The authors thank the EPSRC for funding (grant GR/R81459 and a PhD studentship).

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