5,6-Di-oxo-1,10-phenanthrolin-1-ium trifluoro-methane-sulfonate.

In the structure of the title salt, C(12)H(7)N(2)O(2) (+)·CF(3)SO(3) (-), the cation participates in hydrogen bonding with the dione group of an adjacent cation as well as with the trifluoro-methane-sulfonate anion. In addition, there is an extensive network of C-H⋯O inter-actions between the cations and anions. There are two formula units per asymmetric unit. The crystal studied exhibits inversion twinning.

Related literature

For literature on the coordinating ability of phendione, see: Calderazzo et al. (1999 ▶, 2002 ▶); Calucci et al. (2006 ▶); Fox et al. (1991 ▶); Galet et al. (2005 ▶); Lei et al. (1996 ▶); Okamura et al. (2006 ▶); Paw & Eisenberg (1997 ▶); Ruiz et al. (1999 ▶); Shavaleev et al. (2003a ▶,b ▶); Ma et al. (2002 ▶). For our own reports on n class="Chemical">phendione, see: Onuegbu et al. (2007 ▶); Udeochu et al. (2007 ▶).

Experimental

Crystal data

C12H7N2O2 +·n class="Chemical">CF3O3S−

M = 360.27

Monoclinic,

a = 6.4896 (2) Å

b = 16.3963 (5) Å

c = 13.2430 (3) Å

β = 94.393 (2)°

V = 1404.99 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 200 (2) K

0.51 × 0.22 × 0.18 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007 ▶) T min = 0.897, T max = 1.000 (expected range = 0.850–0.948)

13319 measured reflections

7960 independent reflections

5208 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.076

S = 0.94

7960 reflections

434 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), with 2713 Friedel pairs

Flack parameter: 0.40 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis n class="Disease">RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016632/ng2417sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016632/ng2417Isup2.hkl

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

C12H7N2O2+·CF3O3S–	F000 = 728
Mr = 360.27	Dx = 1.703 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
a = 6.4896 (2) Å	Cell parameters from 5857 reflections
b = 16.3963 (5) Å	θ = 4.7–32.5º
c = 13.2430 (3) Å	µ = 0.30 mm−1
β = 94.393 (2)º	T = 200 (2) K
V = 1404.99 (7) Å3	Needle, yellow-orange
Z = 4	0.51 × 0.22 × 0.18 mm

Oxford Diffraction Gemini diffractometer	7960 independent reflections
Radiation source: fine-focus sealed tube	5208 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 10.5081 pixels mm-1	θmax = 32.5º
T = 200(2) K	θmin = 4.7º
φ and ω scans	h = −9→7
Absorption correction: multi-scan[Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2007)]	k = −24→21
Tmin = 0.897, Tmax = 1.000	l = −19→19
13319 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077	(Δ/σ)max = 0.001
S = 0.94	Δρmax = 0.24 e Å−3
7960 reflections	Δρmin = −0.38 e Å−3
434 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), with 2713 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.40 (5)
Secondary atom site location: difference Fourier map

Experimental. The data were measured to a 2θ limit of 50 °, but the low completeness was caused by

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.

	x	y	z	Uiso*/Ueq
S1	0.64118 (7)	0.25922 (3)	0.84492 (4)	0.02642 (11)
S2	0.86022 (7)	0.38484 (3)	0.23321 (3)	0.02618 (11)
F11	0.7237 (3)	0.10424 (9)	0.86156 (13)	0.0732 (5)
F12	0.9730 (2)	0.17770 (11)	0.81474 (14)	0.0735 (5)
F13	0.7153 (2)	0.14825 (10)	0.70995 (11)	0.0604 (4)
F21	0.7945 (2)	0.49049 (10)	0.37563 (11)	0.0648 (4)
F22	0.7727 (3)	0.54033 (10)	0.22511 (15)	0.0759 (5)
F23	0.5298 (2)	0.46511 (10)	0.27365 (13)	0.0636 (4)
O11	0.7135 (2)	0.26580 (11)	0.94979 (10)	0.0419 (4)
O12	0.7202 (2)	0.32177 (10)	0.78073 (11)	0.0340 (3)
O13	0.4246 (2)	0.24330 (10)	0.82584 (11)	0.0376 (4)
O21	1.0772 (2)	0.40075 (10)	0.25085 (11)	0.0390 (4)
O22	0.7848 (2)	0.32033 (9)	0.29570 (11)	0.0346 (4)
O23	0.7822 (2)	0.38146 (11)	0.12885 (10)	0.0422 (4)
O1A	−0.2484 (2)	0.12049 (10)	0.20079 (13)	0.0400 (4)
O2A	−0.2548 (2)	0.12362 (10)	0.40583 (13)	0.0457 (4)
O1B	1.7556 (2)	0.51876 (9)	0.87690 (12)	0.0386 (4)
O2B	1.7531 (2)	0.52437 (10)	0.67146 (12)	0.0431 (4)
N1A	0.4031 (2)	0.24850 (11)	0.22669 (12)	0.0254 (4)
H1AB	0.5045	0.2692	0.2666	0.030*
N2A	0.4147 (3)	0.24527 (12)	0.42945 (13)	0.0319 (4)
N1B	1.1004 (2)	0.39478 (11)	0.85110 (12)	0.0258 (4)
H1BB	1.0012	0.3723	0.8115	0.031*
N2B	1.0923 (3)	0.39406 (12)	0.64828 (13)	0.0327 (4)
C1	0.7697 (4)	0.16729 (15)	0.80584 (17)	0.0387 (6)
C2	0.7337 (4)	0.47486 (15)	0.27958 (18)	0.0402 (6)
C1A	0.4191 (3)	0.25021 (14)	0.12634 (15)	0.0314 (5)
H1AA	0.5384	0.2729	0.0999	0.038*
C2A	0.2629 (3)	0.21907 (14)	0.06179 (17)	0.0322 (5)
H2AA	0.2737	0.2197	−0.0093	0.039*
C3A	0.0900 (3)	0.18683 (13)	0.10145 (17)	0.0301 (5)
H3AA	−0.0202	0.1658	0.0577	0.036*
C4A	0.0781 (3)	0.18525 (12)	0.20630 (15)	0.0241 (4)
C5A	−0.1030 (3)	0.14900 (13)	0.25125 (17)	0.0289 (5)
C6A	−0.1038 (3)	0.14924 (13)	0.36802 (17)	0.0315 (5)
C7A	0.0806 (3)	0.18109 (13)	0.42748 (16)	0.0288 (5)
C8A	0.0996 (4)	0.17678 (15)	0.53295 (16)	0.0389 (5)
H8AA	−0.0078	0.1535	0.5684	0.047*
C9A	0.2741 (4)	0.20637 (15)	0.58490 (18)	0.0444 (6)
H9AA	0.2901	0.2038	0.6567	0.053*
C10A	0.4267 (4)	0.23999 (16)	0.53074 (17)	0.0432 (6)
H10B	0.5472	0.2606	0.5674	0.052*
C11A	0.2440 (3)	0.21495 (12)	0.37991 (15)	0.0246 (4)
C12A	0.2397 (3)	0.21671 (12)	0.26908 (15)	0.0216 (4)
C1B	1.0812 (3)	0.39649 (13)	0.95094 (14)	0.0286 (4)
H1BA	0.9613	0.3742	0.9774	0.034*
C2B	1.2347 (3)	0.43041 (13)	1.01586 (15)	0.0318 (5)
H2BA	1.2203	0.4329	1.0866	0.038*
C3B	1.4085 (3)	0.46050 (13)	0.97591 (15)	0.0305 (5)
H3BA	1.5180	0.4824	1.0194	0.037*
C4B	1.4242 (3)	0.45896 (12)	0.87118 (15)	0.0245 (4)
C5B	1.6077 (3)	0.49192 (13)	0.82586 (16)	0.0284 (5)
C6B	1.6070 (3)	0.49306 (13)	0.70872 (16)	0.0303 (5)
C7B	1.4283 (3)	0.45768 (13)	0.65019 (15)	0.0289 (5)
C8B	1.4144 (4)	0.45842 (15)	0.54424 (17)	0.0393 (6)
H8BA	1.5239	0.4797	0.5085	0.047*
C9B	1.2398 (4)	0.42780 (16)	0.49305 (17)	0.0463 (7)
H9BA	1.2255	0.4283	0.4211	0.056*
C10B	1.0845 (4)	0.39614 (16)	0.54748 (17)	0.0400 (6)
H10A	0.9652	0.3746	0.5108	0.048*
C11B	1.2622 (3)	0.42491 (13)	0.69772 (16)	0.0271 (5)
C12B	1.2647 (3)	0.42594 (12)	0.80881 (15)	0.0240 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0252 (2)	0.0305 (3)	0.0237 (2)	−0.0019 (2)	0.00264 (19)	−0.0019 (2)
S2	0.0248 (2)	0.0314 (3)	0.0226 (2)	−0.0042 (2)	0.00331 (18)	−0.0024 (2)
F11	0.1143 (14)	0.0318 (9)	0.0735 (11)	0.0060 (8)	0.0075 (10)	0.0159 (8)
F12	0.0368 (8)	0.0750 (12)	0.1081 (14)	0.0217 (7)	0.0024 (9)	−0.0140 (11)
F13	0.0798 (11)	0.0579 (11)	0.0435 (8)	0.0118 (8)	0.0049 (8)	−0.0213 (8)
F21	0.0776 (10)	0.0674 (11)	0.0500 (9)	0.0049 (8)	0.0100 (8)	−0.0305 (8)
F22	0.0961 (13)	0.0334 (9)	0.1013 (14)	0.0024 (8)	0.0285 (10)	0.0186 (9)
F23	0.0363 (8)	0.0633 (11)	0.0922 (12)	0.0136 (7)	0.0116 (8)	0.0001 (9)
O11	0.0484 (9)	0.0540 (10)	0.0229 (7)	−0.0107 (8)	−0.0002 (6)	−0.0049 (8)
O12	0.0317 (8)	0.0321 (8)	0.0381 (9)	−0.0046 (6)	0.0024 (6)	0.0069 (7)
O13	0.0217 (7)	0.0516 (11)	0.0399 (8)	−0.0076 (6)	0.0049 (6)	−0.0031 (7)
O21	0.0282 (8)	0.0530 (11)	0.0364 (8)	−0.0054 (7)	0.0052 (6)	−0.0039 (8)
O22	0.0327 (8)	0.0309 (8)	0.0404 (9)	−0.0049 (6)	0.0029 (7)	0.0057 (7)
O23	0.0457 (9)	0.0574 (11)	0.0230 (7)	−0.0121 (8)	0.0003 (6)	−0.0062 (8)
O1A	0.0307 (9)	0.0350 (9)	0.0533 (10)	−0.0088 (7)	−0.0043 (8)	−0.0005 (8)
O2A	0.0434 (9)	0.0411 (10)	0.0555 (10)	−0.0126 (7)	0.0222 (8)	−0.0002 (8)
O1B	0.0320 (8)	0.0346 (9)	0.0485 (9)	−0.0093 (7)	−0.0009 (7)	0.0006 (8)
O2B	0.0392 (9)	0.0411 (10)	0.0517 (10)	−0.0075 (7)	0.0203 (8)	0.0029 (8)
N1A	0.0210 (8)	0.0285 (10)	0.0262 (9)	−0.0027 (7)	−0.0010 (7)	−0.0005 (8)
N2A	0.0312 (9)	0.0345 (11)	0.0293 (9)	0.0017 (8)	−0.0032 (7)	−0.0019 (8)
N1B	0.0229 (8)	0.0292 (10)	0.0253 (8)	−0.0002 (7)	0.0029 (7)	0.0010 (8)
N2B	0.0330 (9)	0.0372 (11)	0.0271 (9)	0.0027 (8)	−0.0025 (7)	−0.0025 (9)
C1	0.0394 (13)	0.0381 (15)	0.0387 (13)	0.0038 (10)	0.0031 (10)	−0.0039 (11)
C2	0.0443 (14)	0.0356 (14)	0.0419 (14)	0.0010 (10)	0.0107 (11)	0.0003 (11)
C1A	0.0306 (11)	0.0344 (13)	0.0300 (11)	−0.0026 (9)	0.0079 (9)	0.0066 (11)
C2A	0.0375 (13)	0.0355 (13)	0.0238 (11)	0.0049 (9)	0.0041 (9)	0.0040 (10)
C3A	0.0310 (11)	0.0265 (12)	0.0319 (12)	0.0017 (8)	−0.0045 (10)	0.0019 (9)
C4A	0.0271 (11)	0.0184 (10)	0.0266 (10)	0.0017 (8)	0.0019 (9)	0.0005 (8)
C5A	0.0258 (11)	0.0200 (11)	0.0417 (13)	0.0024 (8)	0.0073 (9)	0.0004 (10)
C6A	0.0356 (12)	0.0199 (11)	0.0403 (12)	0.0027 (9)	0.0101 (9)	−0.0012 (9)
C7A	0.0334 (11)	0.0234 (11)	0.0302 (11)	0.0021 (8)	0.0058 (9)	−0.0007 (9)
C8A	0.0489 (14)	0.0395 (13)	0.0301 (12)	0.0058 (11)	0.0155 (10)	0.0058 (10)
C9A	0.0619 (17)	0.0460 (16)	0.0253 (11)	0.0075 (12)	0.0035 (11)	0.0035 (11)
C10A	0.0506 (14)	0.0438 (16)	0.0331 (12)	0.0044 (11)	−0.0100 (11)	−0.0022 (11)
C11A	0.0258 (10)	0.0240 (11)	0.0240 (10)	0.0009 (8)	0.0027 (8)	−0.0020 (9)
C12A	0.0198 (10)	0.0210 (11)	0.0247 (10)	0.0019 (7)	0.0063 (8)	0.0006 (9)
C1B	0.0270 (10)	0.0299 (12)	0.0297 (10)	0.0019 (8)	0.0070 (8)	0.0036 (10)
C2B	0.0400 (12)	0.0339 (12)	0.0215 (10)	−0.0014 (9)	0.0024 (9)	0.0033 (9)
C3B	0.0341 (11)	0.0292 (12)	0.0271 (11)	−0.0014 (8)	−0.0056 (9)	−0.0014 (9)
C4B	0.0253 (10)	0.0209 (10)	0.0272 (11)	0.0042 (8)	0.0009 (9)	0.0025 (9)
C5B	0.0277 (11)	0.0211 (11)	0.0361 (11)	0.0032 (8)	0.0011 (9)	0.0037 (9)
C6B	0.0322 (12)	0.0242 (12)	0.0357 (12)	0.0060 (9)	0.0106 (9)	0.0037 (10)
C7B	0.0350 (12)	0.0272 (11)	0.0253 (10)	0.0061 (8)	0.0078 (9)	0.0045 (9)
C8B	0.0535 (15)	0.0378 (13)	0.0282 (12)	0.0080 (11)	0.0137 (11)	0.0028 (11)
C9B	0.0656 (18)	0.0520 (16)	0.0208 (11)	0.0117 (13)	0.0006 (12)	−0.0013 (11)
C10B	0.0466 (13)	0.0407 (15)	0.0312 (12)	0.0047 (11)	−0.0072 (10)	−0.0047 (11)
C11B	0.0315 (11)	0.0258 (11)	0.0243 (10)	0.0066 (9)	0.0033 (9)	0.0019 (9)
C12B	0.0241 (10)	0.0209 (11)	0.0270 (10)	0.0053 (8)	0.0008 (8)	0.0033 (9)

S1—O13	1.4330 (14)	C3A—C4A	1.397 (3)
S1—O11	1.4355 (15)	C3A—H3AA	0.9500
S1—O12	1.4507 (16)	C4A—C12A	1.387 (3)
S1—C1	1.817 (2)	C4A—C5A	1.482 (3)
S2—O21	1.4337 (14)	C5A—C6A	1.547 (3)
S2—O23	1.4362 (14)	C6A—C7A	1.477 (3)
S2—O22	1.4509 (16)	C7A—C11A	1.390 (3)
S2—C2	1.819 (2)	C7A—C8A	1.394 (3)
F11—C1	1.318 (3)	C8A—C9A	1.369 (3)
F12—C1	1.327 (3)	C8A—H8AA	0.9500
F13—C1	1.329 (3)	C9A—C10A	1.381 (4)
F21—C2	1.328 (3)	C9A—H9AA	0.9500
F22—C2	1.328 (3)	C10A—H10B	0.9500
F23—C2	1.329 (3)	C11A—C12A	1.466 (3)
O1A—C5A	1.208 (2)	C1B—C2B	1.382 (3)
O2A—C6A	1.209 (2)	C1B—H1BA	0.9500
O1B—C5B	1.214 (2)	C2B—C3B	1.374 (3)
O2B—C6B	1.216 (2)	C2B—H2BA	0.9500
N1A—C1A	1.341 (3)	C3B—C4B	1.399 (3)
N1A—C12A	1.343 (2)	C3B—H3BA	0.9500
N1A—H1AB	0.8800	C4B—C12B	1.384 (3)
N2A—C11A	1.339 (2)	C4B—C5B	1.476 (3)
N2A—C10A	1.340 (3)	C5B—C6B	1.551 (3)
N1B—C1B	1.338 (2)	C6B—C7B	1.464 (3)
N1B—C12B	1.343 (3)	C7B—C11B	1.396 (3)
N1B—H1BB	0.8800	C7B—C8B	1.399 (3)
N2B—C10B	1.332 (3)	C8B—C9B	1.371 (3)
N2B—C11B	1.338 (3)	C8B—H8BA	0.9500
C1A—C2A	1.373 (3)	C9B—C10B	1.384 (3)
C1A—H1AA	0.9500	C9B—H9BA	0.9500
C2A—C3A	1.380 (3)	C10B—H10A	0.9500
C2A—H2AA	0.9500	C11B—C12B	1.470 (3)
O13—S1—O11	115.34 (9)	C8A—C7A—C6A	121.5 (2)
O13—S1—O12	114.30 (9)	C9A—C8A—C7A	119.5 (2)
O11—S1—O12	114.19 (9)	C9A—C8A—H8AA	120.3
O13—S1—C1	105.30 (10)	C7A—C8A—H8AA	120.3
O11—S1—C1	102.40 (10)	C8A—C9A—C10A	118.6 (2)
O12—S1—C1	103.23 (10)	C8A—C9A—H9AA	120.7
O21—S2—O23	115.69 (9)	C10A—C9A—H9AA	120.7
O21—S2—O22	114.19 (9)	N2A—C10A—C9A	123.8 (2)
O23—S2—O22	114.28 (9)	N2A—C10A—H10B	118.1
O21—S2—C2	105.11 (11)	C9A—C10A—H10B	118.1
O23—S2—C2	102.77 (11)	N2A—C11A—C7A	123.88 (19)
O22—S2—C2	102.61 (10)	N2A—C11A—C12A	115.77 (18)
C1A—N1A—C12A	123.07 (17)	C7A—C11A—C12A	120.33 (17)
C1A—N1A—H1AB	118.5	N1A—C12A—C4A	118.63 (17)
C12A—N1A—H1AB	118.5	N1A—C12A—C11A	118.10 (16)
C11A—N2A—C10A	116.7 (2)	C4A—C12A—C11A	123.25 (17)
C1B—N1B—C12B	122.78 (17)	N1B—C1B—C2B	120.40 (18)
C1B—N1B—H1BB	118.6	N1B—C1B—H1BA	119.8
C12B—N1B—H1BB	118.6	C2B—C1B—H1BA	119.8
C10B—N2B—C11B	116.6 (2)	C3B—C2B—C1B	118.62 (19)
F11—C1—F12	108.5 (2)	C3B—C2B—H2BA	120.7
F11—C1—F13	107.22 (19)	C1B—C2B—H2BA	120.7
F12—C1—F13	107.7 (2)	C2B—C3B—C4B	119.98 (19)
F11—C1—S1	111.27 (16)	C2B—C3B—H3BA	120.0
F12—C1—S1	110.05 (16)	C4B—C3B—H3BA	120.0
F13—C1—S1	111.92 (16)	C12B—C4B—C3B	119.40 (19)
F21—C2—F22	108.0 (2)	C12B—C4B—C5B	119.35 (18)
F21—C2—F23	107.5 (2)	C3B—C4B—C5B	121.25 (18)
F22—C2—F23	107.18 (19)	O1B—C5B—C4B	122.31 (19)
F21—C2—S2	111.81 (17)	O1B—C5B—C6B	119.62 (18)
F22—C2—S2	111.26 (16)	C4B—C5B—C6B	118.06 (17)
F23—C2—S2	110.84 (16)	O2B—C6B—C7B	124.3 (2)
N1A—C1A—C2A	119.98 (19)	O2B—C6B—C5B	117.92 (19)
N1A—C1A—H1AA	120.0	C7B—C6B—C5B	117.79 (18)
C2A—C1A—H1AA	120.0	C11B—C7B—C8B	117.6 (2)
C1A—C2A—C3A	119.2 (2)	C11B—C7B—C6B	121.40 (19)
C1A—C2A—H2AA	120.4	C8B—C7B—C6B	121.0 (2)
C3A—C2A—H2AA	120.4	C9B—C8B—C7B	118.7 (2)
C2A—C3A—C4A	119.6 (2)	C9B—C8B—H8BA	120.7
C2A—C3A—H3AA	120.2	C7B—C8B—H8BA	120.7
C4A—C3A—H3AA	120.2	C8B—C9B—C10B	119.2 (2)
C12A—C4A—C3A	119.47 (18)	C8B—C9B—H9BA	120.4
C12A—C4A—C5A	119.66 (18)	C10B—C9B—H9BA	120.4
C3A—C4A—C5A	120.85 (19)	N2B—C10B—C9B	123.9 (2)
O1A—C5A—C4A	122.9 (2)	N2B—C10B—H10A	118.0
O1A—C5A—C6A	119.47 (19)	C9B—C10B—H10A	118.0
C4A—C5A—C6A	117.65 (18)	N2B—C11B—C7B	124.1 (2)
O2A—C6A—C7A	123.4 (2)	N2B—C11B—C12B	116.08 (19)
O2A—C6A—C5A	118.55 (19)	C7B—C11B—C12B	119.79 (18)
C7A—C6A—C5A	118.00 (18)	N1B—C12B—C4B	118.77 (18)
C11A—C7A—C8A	117.5 (2)	N1B—C12B—C11B	117.69 (17)
C11A—C7A—C6A	120.98 (19)	C4B—C12B—C11B	123.52 (18)
O13—S1—C1—F11	−63.50 (18)	C1A—N1A—C12A—C11A	177.25 (18)
O11—S1—C1—F11	57.46 (18)	C3A—C4A—C12A—N1A	0.5 (3)
O12—S1—C1—F11	176.32 (16)	C5A—C4A—C12A—N1A	179.33 (19)
O13—S1—C1—F12	176.18 (16)	C3A—C4A—C12A—C11A	−177.69 (18)
O11—S1—C1—F12	−62.86 (19)	C5A—C4A—C12A—C11A	1.1 (3)
O12—S1—C1—F12	56.00 (19)	N2A—C11A—C12A—N1A	−0.5 (3)
O13—S1—C1—F13	56.44 (19)	C7A—C11A—C12A—N1A	−178.6 (2)
O11—S1—C1—F13	177.40 (16)	N2A—C11A—C12A—C4A	177.71 (19)
O12—S1—C1—F13	−63.74 (19)	C7A—C11A—C12A—C4A	−0.4 (3)
O21—S2—C2—F21	−55.78 (19)	C12B—N1B—C1B—C2B	−0.7 (3)
O23—S2—C2—F21	−177.22 (16)	N1B—C1B—C2B—C3B	−1.4 (3)
O22—S2—C2—F21	63.91 (19)	C1B—C2B—C3B—C4B	2.2 (3)
O21—S2—C2—F22	65.10 (18)	C2B—C3B—C4B—C12B	−0.9 (3)
O23—S2—C2—F22	−56.34 (18)	C2B—C3B—C4B—C5B	179.1 (2)
O22—S2—C2—F22	−175.21 (16)	C12B—C4B—C5B—O1B	−177.13 (19)
O21—S2—C2—F23	−175.74 (16)	C3B—C4B—C5B—O1B	2.9 (3)
O23—S2—C2—F23	62.82 (18)	C12B—C4B—C5B—C6B	3.9 (3)
O22—S2—C2—F23	−56.05 (18)	C3B—C4B—C5B—C6B	−176.08 (17)
C12A—N1A—C1A—C2A	0.5 (3)	O1B—C5B—C6B—O2B	−3.0 (3)
N1A—C1A—C2A—C3A	0.5 (3)	C4B—C5B—C6B—O2B	176.0 (2)
C1A—C2A—C3A—C4A	−1.0 (3)	O1B—C5B—C6B—C7B	178.08 (19)
C2A—C3A—C4A—C12A	0.5 (3)	C4B—C5B—C6B—C7B	−2.9 (3)
C2A—C3A—C4A—C5A	−178.3 (2)	O2B—C6B—C7B—C11B	−177.9 (2)
C12A—C4A—C5A—O1A	−179.9 (2)	C5B—C6B—C7B—C11B	0.9 (3)
C3A—C4A—C5A—O1A	−1.0 (3)	O2B—C6B—C7B—C8B	−0.5 (3)
C12A—C4A—C5A—C6A	0.9 (3)	C5B—C6B—C7B—C8B	178.34 (19)
C3A—C4A—C5A—C6A	179.67 (18)	C11B—C7B—C8B—C9B	0.5 (3)
O1A—C5A—C6A—O2A	−2.9 (3)	C6B—C7B—C8B—C9B	−177.1 (2)
C4A—C5A—C6A—O2A	176.4 (2)	C7B—C8B—C9B—C10B	−0.9 (4)
O1A—C5A—C6A—C7A	177.2 (2)	C11B—N2B—C10B—C9B	0.0 (4)
C4A—C5A—C6A—C7A	−3.5 (3)	C8B—C9B—C10B—N2B	0.7 (4)
O2A—C6A—C7A—C11A	−175.5 (2)	C10B—N2B—C11B—C7B	−0.6 (3)
C5A—C6A—C7A—C11A	4.3 (3)	C10B—N2B—C11B—C12B	177.13 (18)
O2A—C6A—C7A—C8A	5.9 (3)	C8B—C7B—C11B—N2B	0.3 (3)
C5A—C6A—C7A—C8A	−174.27 (19)	C6B—C7B—C11B—N2B	177.9 (2)
C11A—C7A—C8A—C9A	0.7 (3)	C8B—C7B—C11B—C12B	−177.29 (18)
C6A—C7A—C8A—C9A	179.4 (2)	C6B—C7B—C11B—C12B	0.3 (3)
C7A—C8A—C9A—C10A	0.2 (4)	C1B—N1B—C12B—C4B	2.1 (3)
C11A—N2A—C10A—C9A	−0.7 (4)	C1B—N1B—C12B—C11B	−176.33 (18)
C8A—C9A—C10A—N2A	−0.2 (4)	C3B—C4B—C12B—N1B	−1.3 (3)
C10A—N2A—C11A—C7A	1.7 (3)	C5B—C4B—C12B—N1B	178.77 (18)
C10A—N2A—C11A—C12A	−176.33 (18)	C3B—C4B—C12B—C11B	177.07 (17)
C8A—C7A—C11A—N2A	−1.8 (3)	C5B—C4B—C12B—C11B	−2.9 (3)
C6A—C7A—C11A—N2A	179.60 (19)	N2B—C11B—C12B—N1B	1.3 (3)
C8A—C7A—C11A—C12A	176.19 (18)	C7B—C11B—C12B—N1B	179.1 (2)
C6A—C7A—C11A—C12A	−2.4 (3)	N2B—C11B—C12B—C4B	−177.06 (19)
C1A—N1A—C12A—C4A	−1.0 (3)	C7B—C11B—C12B—C4B	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O22	0.88	2.01	2.830 (2)	154
N1B—H1BB···O12	0.88	2.02	2.835 (2)	154
C1A—H1AA···O11i	0.95	2.37	3.141 (3)	138
C1A—H1AA···O23	0.95	2.39	3.190 (3)	141
C1B—H1BA···O11	0.95	2.41	3.206 (3)	142
C1B—H1BA···O23ii	0.95	2.40	3.175 (2)	139
C2A—H2AA···O13i	0.95	2.49	3.395 (3)	159
C9A—H9AA···O13	0.95	2.43	3.320 (3)	156
C2B—H2BA···O21ii	0.95	2.49	3.384 (3)	158
C9B—H9BA···O21	0.95	2.43	3.328 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AB⋯O22	0.88	2.01	2.830 (2)	154
N1B—H1BB⋯O12	0.88	2.02	2.835 (2)	154