Tricarbonyl[tris(1-methyl-1H-imidazol-2-yl-κN(3))methanol]manganese(I) trifluoromethanesulfonate.

In the title compound, [Mn(C(13)H(16)N(6)O)(CO)(3)](CF(3)O(3)S), the Mn(I) atom has a slightly distorted octa-hedral geometry. The three CO ligands have C-Mn-C angles in the range 89.44 (10)-92.31 (9)°, while the three N atoms of the tripodal ligand form significantly smaller N-Mn-N angles of 82.76 (2)-85.51 (6)°. The three N atoms of the tripodal ligand and the three carbonyl ligands coordinate facially. In the crystal, the trifluoro-methane-sulfonate counter anion is connected by a medium-strength O-H⋯O hydrogen bond to the hydroxyl group of the manganese complex.

Related literature

For the structures of related complexes, see: Niesel et al. (2008 ▶); Herrick et al. (2008 ▶); Kunz et al. (2009 ▶). For details of the chemistry of tris­(imidazolyl-2-yl)carbinol ligands, see: Stamatatos et al. (2009 ▶); Breslow et al. (1983 ▶); Tang et al. (1978 ▶). For details of the chemistry of n class="Chemical">Mn(CO)3 complexes, see: Kreiter et al. (1994 ▶, 1995 ▶); Brückmann et al. (2011 ▶); Huber et al. (2012 ▶); Berends & Kurz (2012 ▶).

Experimental

Crystal data

[Mn(CO)3(C13H16N6O)](n class="Chemical">CF3O3S)

M = 560.36

Monoclinic,

a = 12.16673 (18) Å

b = 15.5692 (2) Å

c = 12.6240 (2) Å

β = 104.6721 (16)°

V = 2313.33 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 290 K

0.80 × 0.74 × 0.40 mm

Data collection

Oxford Xcalibur diffractometer with Eos detector

Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2009 ▶) T min = 0.805, T max = 1.000

95191 measured reflections

6746 independent reflections

5888 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.084

S = 1.06

6746 reflections

330 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035891/pk2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035891/pk2428Isup2.hkl

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

[Mn(C13H16N6O)(CO)3]·CF3O3S	F(000) = 1136
Mr = 560.36	Dx = 1.609 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 50962 reflections
a = 12.16673 (18) Å	θ = 3.0–31.7°
b = 15.5692 (2) Å	µ = 0.74 mm−1
c = 12.6240 (2) Å	T = 290 K
β = 104.6721 (16)°	Block, yellow
V = 2313.33 (6) Å3	0.80 × 0.74 × 0.40 mm
Z = 4

Oxford Xcalibur with Eos detector? diffractometer	6746 independent reflections
Radiation source: fine-focus sealed tube	5888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 16.2711 pixels mm-1	θmax = 30.0°, θmin = 3.0°
ω scans	h = −17→17
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2009)	k = −21→21
Tmin = 0.805, Tmax = 1.000	l = −17→17
95191 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.015P)2 + 2.P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
6746 reflections	Δρmax = 0.37 e Å−3
330 parameters	Δρmin = −0.51 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00166 (17)

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
Mn1	0.10254 (2)	0.295254 (17)	0.16048 (2)	0.03656 (8)
O1	0.35083 (11)	0.49536 (9)	0.35279 (11)	0.0412 (3)
H1	0.4054 (19)	0.4867 (14)	0.3424 (18)	0.044 (6)*
N1	0.19095 (13)	0.38711 (10)	0.10358 (12)	0.0389 (3)
C1	0.27555 (12)	0.43432 (10)	0.29428 (13)	0.0315 (3)
O2	−0.11219 (16)	0.32763 (15)	−0.00447 (16)	0.0896 (6)
N2	0.07555 (11)	0.39388 (10)	0.26080 (12)	0.0354 (3)
C2	0.25808 (13)	0.44160 (10)	0.17035 (14)	0.0333 (3)
O3	−0.02144 (16)	0.17630 (12)	0.27000 (15)	0.0730 (5)
N3	0.25271 (12)	0.27691 (9)	0.27527 (12)	0.0370 (3)
C3	0.18358 (19)	0.41522 (14)	−0.00092 (16)	0.0503 (5)
H3	0.1420	0.3890	−0.0647	0.060 (7)*
O4	0.16020 (19)	0.15860 (12)	0.02292 (16)	0.0834 (6)
N4	0.29270 (13)	0.50443 (10)	0.11247 (13)	0.0416 (3)
C4	0.2463 (2)	0.48683 (15)	0.00382 (17)	0.0542 (5)
H4	0.2563	0.5185	−0.0555	0.070 (8)*
N5	0.11867 (12)	0.50560 (9)	0.37074 (12)	0.0369 (3)
C5	0.35957 (19)	0.58200 (14)	0.1479 (2)	0.0597 (6)
H5A	0.3280	0.6129	0.1991	0.090*
H5B	0.3579	0.6177	0.0855	0.090*
H5C	0.4367	0.5664	0.1823	0.090*
N6	0.38841 (12)	0.31476 (10)	0.41865 (13)	0.0418 (3)
C6	0.15755 (13)	0.44636 (10)	0.31180 (13)	0.0314 (3)
C7	−0.02132 (14)	0.42127 (13)	0.28780 (16)	0.0434 (4)
H7	−0.0929	0.3967	0.2634	0.051 (6)*
C8	0.00426 (15)	0.48947 (13)	0.35522 (16)	0.0452 (4)
H8	−0.0459	0.5200	0.3857	0.052 (6)*
C9	0.18119 (19)	0.57170 (14)	0.44384 (18)	0.0539 (5)
H9A	0.2387	0.5451	0.5008	0.081*
H9B	0.1297	0.6031	0.4758	0.081*
H9C	0.2163	0.6103	0.4030	0.081*
C10	0.30911 (13)	0.34236 (11)	0.32977 (13)	0.0332 (3)
C11	0.30031 (17)	0.20377 (13)	0.32892 (18)	0.0476 (4)
H11	0.2788	0.1478	0.3077	0.051 (6)*
C12	0.38308 (18)	0.22648 (14)	0.41719 (18)	0.0522 (5)
H12	0.4282	0.1894	0.4678	0.064 (7)*
C13	0.46166 (19)	0.36356 (16)	0.50876 (17)	0.0602 (6)
H13A	0.5207	0.3913	0.4834	0.090*
H13B	0.4950	0.3252	0.5677	0.090*
H13C	0.4172	0.4061	0.5342	0.090*
C14	−0.02874 (18)	0.31700 (15)	0.05903 (18)	0.0533 (5)
C15	0.13726 (19)	0.21210 (14)	0.07542 (17)	0.0511 (5)
C16	0.02768 (17)	0.22112 (13)	0.22707 (17)	0.0473 (4)
S1	0.61262 (4)	0.42786 (4)	0.23478 (5)	0.05368 (14)
F1	0.7020 (2)	0.30397 (12)	0.36557 (18)	0.1337 (10)
F2	0.7028 (2)	0.28311 (15)	0.2001 (2)	0.1324 (9)
F3	0.55074 (19)	0.26955 (13)	0.24881 (19)	0.1151 (7)
O5	0.55176 (13)	0.45179 (12)	0.31485 (14)	0.0660 (4)
O6	0.72136 (14)	0.46749 (12)	0.25442 (18)	0.0790 (6)
O7	0.54709 (19)	0.42639 (18)	0.12357 (16)	0.1040 (8)
C17	0.6452 (2)	0.31564 (18)	0.2657 (3)	0.0738 (7)

	U11	U22	U33	U12	U13	U23
Mn1	0.03490 (13)	0.03877 (14)	0.03562 (13)	−0.00670 (10)	0.00821 (10)	−0.00727 (10)
O1	0.0303 (6)	0.0422 (7)	0.0499 (7)	−0.0083 (5)	0.0082 (5)	−0.0103 (6)
N1	0.0442 (8)	0.0417 (8)	0.0332 (7)	−0.0027 (6)	0.0141 (6)	−0.0036 (6)
C1	0.0252 (7)	0.0340 (8)	0.0351 (8)	−0.0031 (6)	0.0074 (6)	−0.0034 (6)
O2	0.0612 (11)	0.1112 (17)	0.0761 (13)	0.0058 (11)	−0.0201 (9)	−0.0129 (12)
N2	0.0264 (6)	0.0435 (8)	0.0372 (7)	−0.0023 (5)	0.0095 (5)	−0.0053 (6)
C2	0.0310 (7)	0.0340 (8)	0.0373 (8)	0.0012 (6)	0.0131 (6)	0.0011 (6)
O3	0.0760 (11)	0.0740 (12)	0.0726 (11)	−0.0295 (9)	0.0254 (9)	0.0044 (9)
N3	0.0336 (7)	0.0352 (7)	0.0427 (8)	−0.0006 (5)	0.0105 (6)	0.0001 (6)
C3	0.0645 (13)	0.0548 (12)	0.0345 (9)	−0.0001 (10)	0.0178 (9)	−0.0020 (8)
O4	0.1109 (16)	0.0656 (11)	0.0833 (13)	−0.0103 (11)	0.0426 (12)	−0.0355 (10)
N4	0.0414 (8)	0.0384 (8)	0.0477 (8)	−0.0001 (6)	0.0160 (7)	0.0078 (6)
C4	0.0674 (13)	0.0569 (12)	0.0432 (10)	0.0030 (10)	0.0234 (10)	0.0109 (9)
N5	0.0364 (7)	0.0379 (7)	0.0371 (7)	0.0036 (6)	0.0104 (6)	−0.0036 (6)
C5	0.0559 (12)	0.0425 (11)	0.0765 (15)	−0.0102 (9)	0.0092 (11)	0.0172 (10)
N6	0.0339 (7)	0.0481 (9)	0.0410 (8)	−0.0008 (6)	0.0049 (6)	0.0074 (7)
C6	0.0279 (7)	0.0362 (8)	0.0304 (7)	0.0006 (6)	0.0081 (6)	−0.0021 (6)
C7	0.0271 (7)	0.0551 (11)	0.0496 (10)	0.0005 (7)	0.0130 (7)	−0.0011 (8)
C8	0.0361 (9)	0.0535 (11)	0.0503 (10)	0.0088 (8)	0.0190 (8)	−0.0022 (9)
C9	0.0560 (12)	0.0498 (11)	0.0540 (12)	0.0018 (9)	0.0103 (9)	−0.0200 (9)
C10	0.0265 (7)	0.0385 (8)	0.0351 (8)	−0.0007 (6)	0.0085 (6)	0.0012 (6)
C11	0.0474 (10)	0.0362 (9)	0.0606 (12)	0.0013 (8)	0.0165 (9)	0.0071 (8)
C12	0.0461 (10)	0.0480 (11)	0.0603 (12)	0.0050 (9)	0.0095 (9)	0.0173 (9)
C13	0.0546 (12)	0.0722 (15)	0.0428 (11)	−0.0089 (11)	−0.0080 (9)	0.0071 (10)
C14	0.0488 (11)	0.0585 (12)	0.0485 (11)	−0.0059 (9)	0.0046 (9)	−0.0109 (9)
C15	0.0586 (12)	0.0473 (11)	0.0498 (11)	−0.0125 (9)	0.0180 (9)	−0.0102 (9)
C16	0.0444 (10)	0.0491 (11)	0.0464 (10)	−0.0101 (8)	0.0080 (8)	−0.0088 (8)
S1	0.0363 (2)	0.0724 (4)	0.0550 (3)	0.0099 (2)	0.0165 (2)	0.0156 (3)
F1	0.190 (2)	0.0667 (11)	0.1016 (15)	0.0248 (13)	−0.0427 (15)	0.0090 (10)
F2	0.1315 (18)	0.1085 (16)	0.174 (2)	0.0228 (14)	0.0696 (17)	−0.0448 (16)
F3	0.1188 (16)	0.0877 (13)	0.1425 (18)	−0.0411 (12)	0.0400 (14)	−0.0251 (13)
O5	0.0524 (9)	0.0804 (12)	0.0741 (11)	0.0120 (8)	0.0325 (8)	0.0101 (9)
O6	0.0489 (9)	0.0765 (12)	0.1204 (16)	−0.0028 (8)	0.0379 (10)	0.0115 (11)
O7	0.0862 (14)	0.161 (2)	0.0569 (11)	0.0263 (15)	0.0037 (10)	0.0251 (13)
C17	0.0713 (16)	0.0631 (15)	0.0827 (19)	−0.0039 (13)	0.0116 (14)	−0.0165 (14)

Mn1—C15	1.799 (2)	N5—C8	1.379 (2)
Mn1—C16	1.804 (2)	N5—C9	1.461 (2)
Mn1—C14	1.808 (2)	C5—H5A	0.9600
Mn1—N1	2.0273 (15)	C5—H5B	0.9600
Mn1—N3	2.0441 (15)	C5—H5C	0.9600
Mn1—N2	2.0688 (14)	N6—C10	1.351 (2)
O1—C1	1.3946 (19)	N6—C12	1.376 (3)
O1—H1	0.72 (2)	N6—C13	1.467 (3)
N1—C2	1.322 (2)	C7—C8	1.347 (3)
N1—C3	1.371 (2)	C7—H7	0.9300
C1—C6	1.519 (2)	C8—H8	0.9300
C1—C10	1.525 (2)	C9—H9A	0.9600
C1—C2	1.529 (2)	C9—H9B	0.9600
O2—C14	1.135 (3)	C9—H9C	0.9600
N2—C6	1.324 (2)	C11—C12	1.346 (3)
N2—C7	1.375 (2)	C11—H11	0.9300
C2—N4	1.351 (2)	C12—H12	0.9300
O3—C16	1.141 (2)	C13—H13A	0.9600
N3—C10	1.320 (2)	C13—H13B	0.9600
N3—C11	1.376 (2)	C13—H13C	0.9600
C3—C4	1.343 (3)	S1—O6	1.4234 (17)
C3—H3	0.9300	S1—O7	1.428 (2)
O4—C15	1.142 (3)	S1—O5	1.4449 (16)
N4—C4	1.372 (3)	S1—C17	1.812 (3)
N4—C5	1.462 (3)	F1—C17	1.288 (3)
C4—H4	0.9300	F2—C17	1.314 (3)
N5—C6	1.344 (2)	F3—C17	1.325 (3)
C15—Mn1—C16	92.31 (9)	H5A—C5—H5C	109.5
C15—Mn1—C14	90.62 (10)	H5B—C5—H5C	109.5
C16—Mn1—C14	89.44 (10)	C10—N6—C12	106.58 (16)
C15—Mn1—N1	94.03 (8)	C10—N6—C13	130.15 (17)
C16—Mn1—N1	172.75 (7)	C12—N6—C13	123.03 (17)
C14—Mn1—N1	93.99 (9)	N2—C6—N5	111.42 (14)
C15—Mn1—N3	91.13 (8)	N2—C6—C1	118.49 (14)
C16—Mn1—N3	92.66 (8)	N5—C6—C1	130.06 (14)
C14—Mn1—N3	177.21 (8)	C8—C7—N2	109.01 (16)
N1—Mn1—N3	83.72 (6)	C8—C7—H7	125.5
C15—Mn1—N2	175.58 (8)	N2—C7—H7	125.5
C16—Mn1—N2	90.71 (8)	C7—C8—N5	107.26 (15)
C14—Mn1—N2	92.63 (8)	C7—C8—H8	126.4
N1—Mn1—N2	82.76 (6)	N5—C8—H8	126.4
N3—Mn1—N2	85.51 (6)	N5—C9—H9A	109.5
C1—O1—H1	106.7 (18)	N5—C9—H9B	109.5
C2—N1—C3	106.73 (16)	H9A—C9—H9B	109.5
C2—N1—Mn1	121.61 (11)	N5—C9—H9C	109.5
C3—N1—Mn1	130.91 (14)	H9A—C9—H9C	109.5
O1—C1—C6	110.92 (13)	H9B—C9—H9C	109.5
O1—C1—C10	113.15 (13)	N3—C10—N6	110.77 (15)
C6—C1—C10	105.41 (13)	N3—C10—C1	120.42 (14)
O1—C1—C2	113.20 (13)	N6—C10—C1	128.64 (15)
C6—C1—C2	104.38 (12)	C12—C11—N3	108.87 (18)
C10—C1—C2	109.14 (13)	C12—C11—H11	125.6
C6—N2—C7	106.01 (14)	N3—C11—H11	125.6
C6—N2—Mn1	122.61 (11)	C11—C12—N6	107.24 (17)
C7—N2—Mn1	131.37 (12)	C11—C12—H12	126.4
N1—C2—N4	110.29 (15)	N6—C12—H12	126.4
N1—C2—C1	120.54 (14)	N6—C13—H13A	109.5
N4—C2—C1	128.73 (15)	N6—C13—H13B	109.5
C10—N3—C11	106.49 (15)	H13A—C13—H13B	109.5
C10—N3—Mn1	120.98 (12)	N6—C13—H13C	109.5
C11—N3—Mn1	130.84 (13)	H13A—C13—H13C	109.5
C4—C3—N1	108.91 (18)	H13B—C13—H13C	109.5
C4—C3—H3	125.5	O2—C14—Mn1	177.5 (2)
N1—C3—H3	125.5	O4—C15—Mn1	178.9 (2)
C2—N4—C4	106.87 (16)	O3—C16—Mn1	177.9 (2)
C2—N4—C5	131.21 (17)	O6—S1—O7	116.17 (14)
C4—N4—C5	121.81 (17)	O6—S1—O5	112.63 (12)
C3—C4—N4	107.19 (17)	O7—S1—O5	115.74 (12)
C3—C4—H4	126.4	O6—S1—C17	103.75 (12)
N4—C4—H4	126.4	O7—S1—C17	103.49 (15)
C6—N5—C8	106.29 (14)	O5—S1—C17	102.74 (13)
C6—N5—C9	129.29 (15)	F1—C17—F2	108.8 (3)
C8—N5—C9	124.30 (16)	F1—C17—F3	108.1 (3)
N4—C5—H5A	109.5	F2—C17—F3	105.6 (2)
N4—C5—H5B	109.5	F1—C17—S1	112.37 (19)
H5A—C5—H5B	109.5	F2—C17—S1	111.0 (2)
N4—C5—H5C	109.5	F3—C17—S1	110.8 (2)
C15—Mn1—N1—C2	−135.39 (15)	C7—N2—C6—C1	−177.73 (15)
C14—Mn1—N1—C2	133.71 (15)	Mn1—N2—C6—C1	1.0 (2)
N3—Mn1—N1—C2	−44.69 (14)	C8—N5—C6—N2	−0.3 (2)
N2—Mn1—N1—C2	41.56 (13)	C9—N5—C6—N2	175.87 (18)
C15—Mn1—N1—C3	55.91 (19)	C8—N5—C6—C1	177.59 (17)
C14—Mn1—N1—C3	−35.00 (19)	C9—N5—C6—C1	−6.2 (3)
N3—Mn1—N1—C3	146.60 (18)	O1—C1—C6—N2	179.32 (15)
N2—Mn1—N1—C3	−127.15 (18)	C10—C1—C6—N2	−57.86 (18)
C16—Mn1—N2—C6	132.48 (15)	C2—C1—C6—N2	57.08 (19)
C14—Mn1—N2—C6	−138.05 (15)	O1—C1—C6—N5	1.5 (2)
N1—Mn1—N2—C6	−44.36 (14)	C10—C1—C6—N5	124.35 (18)
N3—Mn1—N2—C6	39.86 (14)	C2—C1—C6—N5	−120.71 (18)
C16—Mn1—N2—C7	−49.16 (17)	C6—N2—C7—C8	−0.4 (2)
C14—Mn1—N2—C7	40.31 (18)	Mn1—N2—C7—C8	−178.98 (13)
N1—Mn1—N2—C7	134.01 (17)	N2—C7—C8—N5	0.2 (2)
N3—Mn1—N2—C7	−141.77 (17)	C6—N5—C8—C7	0.1 (2)
C3—N1—C2—N4	0.9 (2)	C9—N5—C8—C7	−176.38 (18)
Mn1—N1—C2—N4	−170.19 (11)	C11—N3—C10—N6	−2.23 (19)
C3—N1—C2—C1	173.97 (15)	Mn1—N3—C10—N6	164.50 (11)
Mn1—N1—C2—C1	2.9 (2)	C11—N3—C10—C1	−178.01 (15)
O1—C1—C2—N1	178.58 (15)	Mn1—N3—C10—C1	−11.3 (2)
C6—C1—C2—N1	−60.70 (19)	C12—N6—C10—N3	1.9 (2)
C10—C1—C2—N1	51.60 (19)	C13—N6—C10—N3	−172.51 (19)
O1—C1—C2—N4	−9.8 (2)	C12—N6—C10—C1	177.26 (17)
C6—C1—C2—N4	110.93 (18)	C13—N6—C10—C1	2.8 (3)
C10—C1—C2—N4	−136.77 (17)	O1—C1—C10—N3	−173.45 (14)
C15—Mn1—N3—C10	143.22 (14)	C6—C1—C10—N3	65.17 (18)
C16—Mn1—N3—C10	−124.41 (14)	C2—C1—C10—N3	−46.45 (19)
N1—Mn1—N3—C10	49.29 (13)	O1—C1—C10—N6	11.6 (2)
N2—Mn1—N3—C10	−33.90 (13)	C6—C1—C10—N6	−109.79 (18)
C15—Mn1—N3—C11	−53.69 (18)	C2—C1—C10—N6	138.60 (17)
C16—Mn1—N3—C11	38.68 (18)	C10—N3—C11—C12	1.7 (2)
N1—Mn1—N3—C11	−147.62 (17)	Mn1—N3—C11—C12	−163.23 (14)
N2—Mn1—N3—C11	129.18 (17)	N3—C11—C12—N6	−0.5 (2)
C2—N1—C3—C4	−0.2 (2)	C10—N6—C12—C11	−0.8 (2)
Mn1—N1—C3—C4	169.76 (15)	C13—N6—C12—C11	174.13 (19)
N1—C2—N4—C4	−1.3 (2)	O6—S1—C17—F1	60.3 (3)
C1—C2—N4—C4	−173.59 (17)	O7—S1—C17—F1	−178.0 (2)
N1—C2—N4—C5	174.82 (19)	O5—S1—C17—F1	−57.2 (3)
C1—C2—N4—C5	2.5 (3)	O6—S1—C17—F2	−61.8 (2)
N1—C3—C4—N4	−0.6 (2)	O7—S1—C17—F2	59.9 (2)
C2—N4—C4—C3	1.1 (2)	O5—S1—C17—F2	−179.2 (2)
C5—N4—C4—C3	−175.44 (19)	O6—S1—C17—F3	−178.7 (2)
C7—N2—C6—N5	0.5 (2)	O7—S1—C17—F3	−57.0 (2)
Mn1—N2—C6—N5	179.18 (11)	O5—S1—C17—F3	63.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.72 (2)	1.98 (2)	2.694 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5	0.72 (2)	1.98 (2)	2.694 (2)	175 (2)