Chlorido[2,15-dimethyl-3,7,10,14,20-penta-azabicyclo-[14.3.1]eicosa-1(20),2,14,16,18-penta-ene]manganese(II) perchlorate acetonitrile solvate.

The Mn ion in the title complex, [MnCl(C(17)H(27)N(5))]ClO(4)·CH(3)CN, is six-coordinated with a geometry inter-mediate between penta-gonal pyramidal and heavily distorted octa-hedral. In the macrocycle, the pyridinium ring makes a large dihedral angle of 63.70 (9)° with the best plane through the remaining four N atoms. This feature is common for 17-membered N(5) rings, in contrast to their 16- and 15-membered analogues which often form planar N(5) systems. In the crystal, N-H⋯O and C-H⋯O interactions help to establish the packing. The perchlorate counter-ion is rotationally disordered around the chlorine centre, with occupation factors of 0.74 (1) and 0.26 (1).

Related literature

For manganese(II) n class="Chemical">metalloproteins and penta­aza macrocyclic complexes, see, for example: Riley (1999 ▶); Aston et al. (2001 ▶); Patroniak et al. (2004 ▶); Radecka-Paryzek et al. (2005 ▶); Isobe et al. (2005 ▶); Grabolle et al. (2006 ▶). For the crystal structures of similar 17-membered macrocycles, see: Drew et al. (1977 ▶, 1979 ▶); Nelson et al. (1977 ▶); Drew & Nelson (1979 ▶).

Experimental

Crystal data

[MnCl(C17H27N5)]n class="Chemical">ClO4·C2H3N

M = 532.33

Triclinic,

a = 10.0583 (7) Å

b = 10.9118 (7) Å

c = 11.9591 (8) Å

α = 89.492 (5)°

β = 70.195 (6)°

γ = 84.093 (5)°

V = 1227.89 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 293 K

0.4 × 0.2 × 0.1 mm

Data collection

Kuma KM-4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2007 ▶) T min = 0.842, T max = 0.924

9805 measured reflections

4301 independent reflections

3212 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.12

4301 reflections

329 parameters

68 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis 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: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005595/bg2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005595/bg2236Isup2.hkl

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

[MnCl(C17H27N5)]ClO4·C2H3N	Z = 2
Mr = 532.33	F(000) = 554
Triclinic, P1	Dx = 1.440 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0583 (7) Å	Cell parameters from 5931 reflections
b = 10.9118 (7) Å	θ = 3–24°
c = 11.9591 (8) Å	µ = 0.79 mm−1
α = 89.492 (5)°	T = 293 K
β = 70.195 (6)°	Block, colourless
γ = 84.093 (5)°	0.4 × 0.2 × 0.1 mm
V = 1227.89 (14) Å3

Kuma KM-4 CCD diffractometer	4301 independent reflections
Radiation source: fine-focus sealed tube	3212 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2007)	h = −11→8
Tmin = 0.842, Tmax = 0.924	k = −12→12
9805 measured reflections	l = −14→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
4301 reflections	(Δ/σ)max < 0.001
329 parameters	Δρmax = 0.43 e Å−3
68 restraints	Δρmin = −0.43 e Å−3

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	Occ. (<1)
Mn1	0.44426 (5)	0.28963 (4)	0.20642 (4)	0.04702 (19)
Cl1	0.31564 (10)	0.17792 (9)	0.11320 (8)	0.0692 (3)
C1	0.7488 (3)	0.3700 (3)	0.1391 (2)	0.0476 (7)
C2	0.7747 (3)	0.2331 (3)	0.1285 (3)	0.0544 (8)
C21	0.9208 (4)	0.1739 (4)	0.1132 (4)	0.0838 (12)
H21A	0.9209	0.0859	0.1134	0.109*
H21B	0.9492	0.2002	0.1774	0.109*
H21C	0.9862	0.1976	0.0390	0.109*
N3	0.6681 (3)	0.1794 (2)	0.1317 (2)	0.0579 (7)
C4	0.6780 (5)	0.0432 (4)	0.1191 (4)	0.0882 (13)
H4A	0.7750	0.0114	0.0738	0.106*
H4B	0.6173	0.0215	0.0759	0.106*
C5	0.6331 (5)	−0.0152 (3)	0.2403 (5)	0.0938 (14)
H5A	0.6526	−0.1040	0.2289	0.113*
H5B	0.6910	0.0110	0.2842	0.113*
C6	0.4797 (5)	0.0153 (4)	0.3139 (5)	0.0972 (15)
H6A	0.4210	−0.0044	0.2682	0.117*
H6B	0.4571	−0.0350	0.3838	0.117*
N7	0.4460 (3)	0.1468 (3)	0.3517 (3)	0.0682 (8)
H7	0.5139	0.1655	0.3813	0.082*
C8	0.3099 (4)	0.1695 (4)	0.4485 (4)	0.0905 (13)
H8A	0.3115	0.1198	0.5158	0.109*
H8B	0.2339	0.1468	0.4227	0.109*
C9	0.2845 (5)	0.3013 (4)	0.4839 (3)	0.0799 (11)
H9A	0.3599	0.3232	0.5109	0.096*
H9B	0.1953	0.3167	0.5492	0.096*
N10	0.2796 (3)	0.3788 (3)	0.3822 (2)	0.0589 (7)
H10	0.3047	0.4543	0.3933	0.071*
C11	0.1369 (3)	0.3957 (4)	0.3697 (3)	0.0662 (9)
H11A	0.0650	0.4035	0.4482	0.079*
H11B	0.1234	0.3230	0.3304	0.079*
C12	0.1163 (3)	0.5084 (4)	0.2992 (3)	0.0635 (9)
H12A	0.1351	0.5800	0.3367	0.076*
H12B	0.0175	0.5204	0.3045	0.076*
C13	0.2087 (3)	0.5036 (4)	0.1681 (3)	0.0592 (9)
H13A	0.1856	0.4369	0.1272	0.071*
H13B	0.1904	0.5802	0.1315	0.071*
N14	0.3594 (2)	0.4841 (2)	0.1571 (2)	0.0478 (6)
C15	0.4326 (3)	0.5735 (3)	0.1512 (2)	0.0469 (7)
C22	0.3868 (4)	0.7083 (3)	0.1474 (3)	0.0668 (10)
H22A	0.2947	0.7186	0.1391	0.087*
H22B	0.4540	0.7437	0.0810	0.087*
H22C	0.3825	0.7487	0.2197	0.087*
C16	0.5821 (3)	0.5369 (3)	0.1479 (3)	0.0476 (7)
C17	0.6801 (4)	0.6185 (3)	0.1400 (3)	0.0631 (9)
H17A	0.6559	0.7028	0.1380	0.076*
C18	0.8150 (4)	0.5727 (4)	0.1352 (3)	0.0704 (10)
H18A	0.8816	0.6263	0.1340	0.084*
C19	0.8505 (3)	0.4478 (4)	0.1321 (3)	0.0654 (10)
H19A	0.9423	0.4160	0.1254	0.078*
N20	0.6156 (2)	0.4155 (2)	0.1509 (2)	0.0425 (5)
N23	−0.0126 (5)	0.8132 (4)	0.1994 (4)	0.1062 (13)
C24	0.0164 (4)	0.8829 (4)	0.2528 (4)	0.0760 (11)
C25	0.0549 (6)	0.9727 (4)	0.3213 (5)	0.1053 (16)
H251	0.1320	1.0136	0.2699	0.137*
H252	0.0837	0.9318	0.3821	0.137*
H253	−0.0254	1.0322	0.3574	0.137*
Cl2	0.72849 (11)	0.28375 (9)	0.48084 (8)	0.0727 (3)
O1	0.7114 (7)	0.2002 (6)	0.4036 (5)	0.155 (3)	0.744 (7)
O2	0.8302 (5)	0.2290 (5)	0.5320 (5)	0.136 (2)	0.744 (7)
O3	0.6031 (5)	0.3181 (7)	0.5761 (4)	0.156 (3)	0.744 (7)
O4	0.7887 (6)	0.3879 (5)	0.4240 (5)	0.149 (3)	0.744 (7)
O1A	0.6571 (17)	0.3333 (16)	0.4029 (12)	0.150 (8)	0.256 (7)
O2A	0.706 (2)	0.1585 (7)	0.491 (2)	0.194 (10)	0.256 (7)
O3A	0.668 (2)	0.3472 (18)	0.5903 (10)	0.202 (13)	0.256 (7)
O4A	0.8736 (8)	0.297 (2)	0.429 (2)	0.45 (4)	0.256 (7)

	U11	U22	U33	U12	U13	U23
Mn1	0.0438 (3)	0.0503 (3)	0.0490 (3)	−0.0094 (2)	−0.0170 (2)	−0.0083 (2)
Cl1	0.0697 (6)	0.0756 (6)	0.0717 (6)	−0.0229 (5)	−0.0314 (5)	−0.0163 (5)
C1	0.0384 (15)	0.068 (2)	0.0364 (15)	−0.0069 (14)	−0.0123 (12)	−0.0001 (14)
C2	0.0488 (18)	0.070 (2)	0.0444 (17)	0.0035 (16)	−0.0181 (14)	−0.0054 (15)
C21	0.053 (2)	0.102 (3)	0.093 (3)	0.014 (2)	−0.027 (2)	0.005 (2)
N3	0.0594 (17)	0.0550 (16)	0.0611 (17)	0.0056 (13)	−0.0254 (14)	−0.0202 (13)
C4	0.096 (3)	0.065 (2)	0.113 (4)	0.017 (2)	−0.053 (3)	−0.039 (2)
C5	0.119 (4)	0.040 (2)	0.138 (4)	−0.003 (2)	−0.065 (3)	−0.007 (2)
C6	0.107 (4)	0.053 (2)	0.145 (4)	−0.022 (2)	−0.057 (3)	0.013 (3)
N7	0.070 (2)	0.0633 (18)	0.078 (2)	−0.0174 (15)	−0.0311 (17)	0.0106 (16)
C8	0.080 (3)	0.098 (3)	0.089 (3)	−0.020 (3)	−0.021 (2)	0.037 (3)
C9	0.084 (3)	0.098 (3)	0.048 (2)	−0.009 (2)	−0.0101 (19)	0.002 (2)
N10	0.0586 (16)	0.0675 (18)	0.0475 (15)	−0.0065 (14)	−0.0139 (13)	−0.0032 (13)
C11	0.0507 (19)	0.084 (3)	0.053 (2)	−0.0094 (18)	−0.0022 (16)	−0.0102 (18)
C12	0.0380 (17)	0.090 (3)	0.056 (2)	0.0052 (17)	−0.0099 (15)	−0.0180 (18)
C13	0.0404 (16)	0.081 (2)	0.058 (2)	0.0041 (16)	−0.0216 (15)	−0.0095 (17)
N14	0.0386 (13)	0.0638 (17)	0.0399 (13)	0.0000 (12)	−0.0133 (11)	−0.0075 (12)
C15	0.0493 (17)	0.0554 (18)	0.0340 (15)	−0.0048 (14)	−0.0118 (13)	−0.0024 (13)
C22	0.068 (2)	0.056 (2)	0.066 (2)	0.0073 (17)	−0.0138 (18)	0.0016 (17)
C16	0.0473 (17)	0.0570 (19)	0.0406 (15)	−0.0078 (14)	−0.0169 (13)	−0.0062 (13)
C17	0.067 (2)	0.064 (2)	0.062 (2)	−0.0224 (18)	−0.0226 (18)	−0.0012 (17)
C18	0.060 (2)	0.089 (3)	0.074 (2)	−0.035 (2)	−0.0295 (19)	−0.001 (2)
C19	0.0417 (18)	0.099 (3)	0.060 (2)	−0.0172 (19)	−0.0211 (16)	0.005 (2)
N20	0.0366 (12)	0.0502 (14)	0.0414 (13)	−0.0061 (11)	−0.0134 (10)	−0.0028 (11)
N23	0.105 (3)	0.085 (3)	0.138 (4)	−0.012 (2)	−0.052 (3)	−0.015 (3)
C24	0.065 (2)	0.062 (2)	0.102 (3)	−0.0037 (19)	−0.031 (2)	0.009 (2)
C25	0.130 (4)	0.081 (3)	0.125 (4)	−0.022 (3)	−0.066 (4)	0.007 (3)
Cl2	0.0845 (7)	0.0778 (6)	0.0613 (6)	−0.0233 (5)	−0.0277 (5)	−0.0020 (5)
O1	0.182 (5)	0.162 (5)	0.141 (5)	−0.044 (4)	−0.071 (4)	−0.066 (4)
O2	0.143 (4)	0.144 (4)	0.146 (5)	0.012 (3)	−0.088 (4)	0.017 (3)
O3	0.107 (4)	0.252 (7)	0.081 (3)	0.034 (4)	−0.012 (3)	−0.019 (4)
O4	0.164 (5)	0.132 (4)	0.169 (5)	−0.070 (4)	−0.064 (4)	0.062 (4)
O1A	0.168 (11)	0.172 (12)	0.119 (9)	−0.018 (8)	−0.060 (8)	0.029 (8)
O2A	0.227 (14)	0.160 (13)	0.204 (14)	−0.056 (9)	−0.074 (10)	0.006 (9)
O3A	0.226 (16)	0.211 (15)	0.181 (15)	−0.026 (10)	−0.081 (10)	−0.055 (9)
O4A	0.44 (4)	0.45 (4)	0.46 (4)	−0.054 (12)	−0.142 (16)	0.024 (11)

Mn1—N20	2.234 (2)	C11—H11A	0.9700
Mn1—N3	2.326 (3)	C11—H11B	0.9700
Mn1—N7	2.327 (3)	C12—C13	1.526 (4)
Mn1—N10	2.336 (3)	C12—H12A	0.9700
Mn1—N14	2.350 (3)	C12—H12B	0.9700
Mn1—Cl1	2.3934 (9)	C13—N14	1.469 (3)
C1—N20	1.341 (4)	C13—H13A	0.9700
C1—C19	1.376 (4)	C13—H13B	0.9700
C1—C2	1.489 (5)	N14—C15	1.269 (4)
C2—N3	1.263 (4)	C15—C22	1.500 (4)
C2—C21	1.496 (4)	C15—C16	1.502 (4)
C21—H21A	0.9600	C22—H22A	0.9600
C21—H21B	0.9600	C22—H22B	0.9600
C21—H21C	0.9600	C22—H22C	0.9600
N3—C4	1.485 (5)	C16—N20	1.337 (4)
C4—C5	1.520 (6)	C16—C17	1.374 (4)
C4—H4A	0.9700	C17—C18	1.379 (5)
C4—H4B	0.9700	C17—H17A	0.9300
C5—C6	1.498 (6)	C18—C19	1.370 (5)
C5—H5A	0.9700	C18—H18A	0.9300
C5—H5B	0.9700	C19—H19A	0.9300
C6—N7	1.478 (5)	N23—C24	1.118 (5)
C6—H6A	0.9700	C24—C25	1.446 (7)
C6—H6B	0.9700	C25—H251	0.9600
N7—C8	1.463 (5)	C25—H252	0.9600
N7—H7	0.9100	C25—H253	0.9600
C8—C9	1.475 (6)	Cl2—O1	1.367 (3)
C8—H8A	0.9700	Cl2—O2	1.438 (3)
C8—H8B	0.9700	Cl2—O3	1.403 (4)
C9—N10	1.487 (4)	Cl2—O4	1.403 (3)
C9—H9A	0.9700	Cl2—O1A	1.429 (5)
C9—H9B	0.9700	Cl2—O2A	1.406 (5)
N10—C11	1.485 (4)	Cl2—O3A	1.398 (5)
N10—H10	0.9100	Cl2—O4A	1.402 (5)
C11—C12	1.521 (5)
N20—Mn1—N3	68.62 (9)	C9—N10—Mn1	109.3 (2)
N20—Mn1—N7	118.71 (9)	C11—N10—H10	108.4
N3—Mn1—N7	75.97 (10)	C9—N10—H10	108.4
N20—Mn1—N10	105.07 (9)	Mn1—N10—H10	108.4
N3—Mn1—N10	141.85 (9)	N10—C11—C12	113.0 (3)
N7—Mn1—N10	75.11 (10)	N10—C11—H11A	109.0
N20—Mn1—N14	68.58 (8)	C12—C11—H11A	109.0
N3—Mn1—N14	130.50 (9)	N10—C11—H11B	109.0
N7—Mn1—N14	148.65 (10)	C12—C11—H11B	109.0
N10—Mn1—N14	73.60 (9)	H11A—C11—H11B	107.8
N20—Mn1—Cl1	137.26 (7)	C11—C12—C13	115.8 (3)
N3—Mn1—Cl1	100.45 (7)	C11—C12—H12A	108.3
N7—Mn1—Cl1	96.45 (8)	C13—C12—H12A	108.3
N10—Mn1—Cl1	107.03 (7)	C11—C12—H12B	108.3
N14—Mn1—Cl1	94.43 (7)	C13—C12—H12B	108.3
N20—C1—C19	120.6 (3)	H12A—C12—H12B	107.4
N20—C1—C2	114.3 (3)	N14—C13—C12	109.6 (2)
C19—C1—C2	125.1 (3)	N14—C13—H13A	109.7
N3—C2—C1	114.9 (3)	C12—C13—H13A	109.7
N3—C2—C21	127.0 (3)	N14—C13—H13B	109.7
C1—C2—C21	118.2 (3)	C12—C13—H13B	109.7
C2—C21—H21A	109.5	H13A—C13—H13B	108.2
C2—C21—H21B	109.5	C15—N14—C13	121.8 (3)
H21A—C21—H21B	109.5	C15—N14—Mn1	118.56 (19)
C2—C21—H21C	109.5	C13—N14—Mn1	117.3 (2)
H21A—C21—H21C	109.5	N14—C15—C22	127.6 (3)
H21B—C21—H21C	109.5	N14—C15—C16	114.6 (3)
C2—N3—C4	121.2 (3)	C22—C15—C16	117.7 (3)
C2—N3—Mn1	118.2 (2)	C15—C22—H22A	109.5
C4—N3—Mn1	118.7 (2)	C15—C22—H22B	109.5
N3—C4—C5	110.8 (3)	H22A—C22—H22B	109.5
N3—C4—H4A	109.5	C15—C22—H22C	109.5
C5—C4—H4A	109.5	H22A—C22—H22C	109.5
N3—C4—H4B	109.5	H22B—C22—H22C	109.5
C5—C4—H4B	109.5	N20—C16—C17	121.2 (3)
H4A—C4—H4B	108.1	N20—C16—C15	114.4 (3)
C6—C5—C4	114.7 (4)	C17—C16—C15	124.4 (3)
C6—C5—H5A	108.6	C16—C17—C18	118.7 (3)
C4—C5—H5A	108.6	C16—C17—H17A	120.7
C6—C5—H5B	108.6	C18—C17—H17A	120.7
C4—C5—H5B	108.6	C19—C18—C17	119.7 (3)
H5A—C5—H5B	107.6	C19—C18—H18A	120.2
N7—C6—C5	112.2 (3)	C17—C18—H18A	120.2
N7—C6—H6A	109.2	C18—C19—C1	119.3 (3)
C5—C6—H6A	109.2	C18—C19—H19A	120.3
N7—C6—H6B	109.2	C1—C19—H19A	120.3
C5—C6—H6B	109.2	C16—N20—C1	120.3 (2)
H6A—C6—H6B	107.9	C16—N20—Mn1	120.06 (18)
C8—N7—C6	111.9 (3)	C1—N20—Mn1	118.8 (2)
C8—N7—Mn1	107.3 (2)	N23—C24—C25	179.6 (6)
C6—N7—Mn1	117.4 (3)	C24—C25—H251	109.5
C8—N7—H7	106.6	C24—C25—H252	109.5
C6—N7—H7	106.6	H251—C25—H252	109.5
Mn1—N7—H7	106.6	C24—C25—H253	109.5
N7—C8—C9	109.1 (3)	H251—C25—H253	109.5
N7—C8—H8A	109.9	H252—C25—H253	109.5
C9—C8—H8A	109.9	O3A—Cl2—O4A	112.0 (8)
N7—C8—H8B	109.9	O1—Cl2—O3	113.0 (4)
C9—C8—H8B	109.9	O1—Cl2—O4	112.7 (4)
H8A—C8—H8B	108.3	O3—Cl2—O4	111.0 (4)
C8—C9—N10	110.6 (3)	O3A—Cl2—O2A	111.6 (7)
C8—C9—H9A	109.5	O4A—Cl2—O2A	110.8 (8)
N10—C9—H9A	109.5	O3A—Cl2—O1A	108.0 (7)
C8—C9—H9B	109.5	O4A—Cl2—O1A	108.5 (7)
N10—C9—H9B	109.5	O2A—Cl2—O1A	105.7 (7)
H9A—C9—H9B	108.1	O1—Cl2—O2	108.9 (4)
C11—N10—C9	113.3 (3)	O3—Cl2—O2	106.4 (3)
C11—N10—Mn1	109.01 (19)	O4—Cl2—O2	104.1 (3)
N20—C1—C2—N3	0.2 (4)	C9—N10—C11—C12	158.7 (3)
C19—C1—C2—N3	−176.7 (3)	Mn1—N10—C11—C12	−79.3 (3)
N20—C1—C2—C21	179.2 (3)	N10—C11—C12—C13	66.3 (4)
C19—C1—C2—C21	2.2 (5)	C11—C12—C13—N14	−57.5 (4)
C1—C2—N3—C4	178.4 (3)	C12—C13—N14—C15	−92.3 (4)
C21—C2—N3—C4	−0.5 (5)	C12—C13—N14—Mn1	70.2 (3)
C1—C2—N3—Mn1	−17.4 (4)	N20—Mn1—N14—C15	−16.4 (2)
C21—C2—N3—Mn1	163.8 (3)	N3—Mn1—N14—C15	−48.2 (2)
N20—Mn1—N3—C2	19.7 (2)	N7—Mn1—N14—C15	94.0 (3)
N7—Mn1—N3—C2	−109.3 (2)	N10—Mn1—N14—C15	97.6 (2)
N10—Mn1—N3—C2	−67.6 (3)	Cl1—Mn1—N14—C15	−155.9 (2)
N14—Mn1—N3—C2	51.5 (3)	N20—Mn1—N14—C13	−179.5 (2)
Cl1—Mn1—N3—C2	156.6 (2)	N3—Mn1—N14—C13	148.72 (19)
N20—Mn1—N3—C4	−175.6 (3)	N7—Mn1—N14—C13	−69.2 (3)
N7—Mn1—N3—C4	55.3 (3)	N10—Mn1—N14—C13	−65.5 (2)
N10—Mn1—N3—C4	97.0 (3)	Cl1—Mn1—N14—C13	40.94 (19)
N14—Mn1—N3—C4	−143.9 (2)	C13—N14—C15—C22	−3.5 (5)
Cl1—Mn1—N3—C4	−38.8 (3)	Mn1—N14—C15—C22	−165.8 (2)
C2—N3—C4—C5	94.4 (4)	C13—N14—C15—C16	176.4 (2)
Mn1—N3—C4—C5	−69.7 (4)	Mn1—N14—C15—C16	14.0 (3)
N3—C4—C5—C6	65.7 (5)	N14—C15—C16—N20	0.5 (4)
C4—C5—C6—N7	−67.4 (5)	C22—C15—C16—N20	−179.6 (3)
C5—C6—N7—C8	−164.2 (4)	N14—C15—C16—C17	179.1 (3)
C5—C6—N7—Mn1	71.1 (4)	C22—C15—C16—C17	−1.0 (4)
N20—Mn1—N7—C8	122.6 (3)	N20—C16—C17—C18	−0.1 (5)
N3—Mn1—N7—C8	178.2 (3)	C15—C16—C17—C18	−178.6 (3)
N10—Mn1—N7—C8	23.4 (3)	C16—C17—C18—C19	3.4 (5)
N14—Mn1—N7—C8	27.0 (4)	C17—C18—C19—C1	−2.7 (5)
Cl1—Mn1—N7—C8	−82.6 (3)	N20—C1—C19—C18	−1.2 (5)
N20—Mn1—N7—C6	−110.5 (3)	C2—C1—C19—C18	175.5 (3)
N3—Mn1—N7—C6	−54.9 (3)	C17—C16—N20—C1	−3.9 (4)
N10—Mn1—N7—C6	150.3 (3)	C15—C16—N20—C1	174.8 (2)
N14—Mn1—N7—C6	153.9 (3)	C17—C16—N20—Mn1	165.5 (2)
Cl1—Mn1—N7—C6	44.3 (3)	C15—C16—N20—Mn1	−15.8 (3)
C6—N7—C8—C9	178.6 (3)	C19—C1—N20—C16	4.5 (4)
Mn1—N7—C8—C9	−51.3 (4)	C2—C1—N20—C16	−172.5 (3)
N7—C8—C9—N10	60.4 (4)	C19—C1—N20—Mn1	−165.0 (2)
C8—C9—N10—C11	85.5 (4)	C2—C1—N20—Mn1	17.9 (3)
C8—C9—N10—Mn1	−36.3 (4)	N3—Mn1—N20—C16	171.1 (2)
N20—Mn1—N10—C11	125.9 (2)	N7—Mn1—N20—C16	−129.6 (2)
N3—Mn1—N10—C11	−159.6 (2)	N10—Mn1—N20—C16	−48.6 (2)
N7—Mn1—N10—C11	−117.8 (2)	N14—Mn1—N20—C16	16.6 (2)
N14—Mn1—N10—C11	64.2 (2)	Cl1—Mn1—N20—C16	89.0 (2)
Cl1—Mn1—N10—C11	−25.5 (2)	N3—Mn1—N20—C1	−19.29 (19)
N20—Mn1—N10—C9	−109.7 (2)	N7—Mn1—N20—C1	40.0 (2)
N3—Mn1—N10—C9	−35.3 (3)	N10—Mn1—N20—C1	121.0 (2)
N7—Mn1—N10—C9	6.6 (2)	N14—Mn1—N20—C1	−173.8 (2)
N14—Mn1—N10—C9	−171.5 (2)	Cl1—Mn1—N20—C1	−101.4 (2)
Cl1—Mn1—N10—C9	98.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H252···O2i	0.96	2.27	3.168 (6)	156
N7—H7···O1	0.91	2.16	3.050 (6)	165
N10—H10···O3Ai	0.91	2.23	3.13 (2)	169

Table 1

Selected bond lengths (Å)

Mn1—N20	2.234 (2)
Mn1—N3	2.326 (3)
Mn1—N7	2.327 (3)
Mn1—N10	2.336 (3)
Mn1—N14	2.350 (3)
Mn1—Cl1	2.3934 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H252⋯O2i	0.96	2.27	3.168 (6)	156
N7—H7⋯O1	0.91	2.16	3.050 (6)	165
N10—H10⋯O3Ai	0.91	2.23	3.13 (2)	169

Symmetry code: (i) .