Bis[(2-methyl-benz-yl)bis-(pyridin-2-ylmethyl-κN)amine-κN]manganese(II) bis-(perchlorate).

In the title complex, [Mn(C20H21N3)2](ClO4)2, two tridentate (2-methyl-benz-yl)bis-(pyridin-2-ylmeth-yl)amine (L) ligands form the Mn(II) complex [MnL 2](ClO4)2. The Mn(II) ion lies on a twofold axis and the complex cation is significantly distorted from regular octa-hedral geometry. The packing is stabilized by weak C-H⋯O inter-actions between the cations and anions, which link them into a zigzag ribbon along [101]. The perchlorate anion is disordered and was constrained to be tetra-hedral with two orientations having occupancies of 0.768 (4) and 0.232 (4). The 2-methylbenzyl moiety is also disordered over two sets of sites, with occupancies of 0.508 (15) and 0.492 (15).

Related literature

For the importance of flexible coordination complexes of Mn in biomimetic chemistry, see: Zhou et al. (2011 ▶); Walsdorff et al. (1999 ▶); Nielsen et al. (2007 ▶); Routasalo et al. (2008 ▶), in catalysis, see: Raycroft et al. (2012 ▶); Berthet et al. (2013 ▶), in medicinal chemistry, see: Ari et al. (2013 ▶); Chang et al. (2004 ▶), in O2 activation and catalysis of redox reactions and oxygenation of organic substrates, see: Karlin et al. (1984 ▶); Karlin & Gultneh (1987 ▶); Hatcher & Karlin (2004 ▶) and in making polymeric materials that form by self-assembling metal coord­ination compounds, see: Denmark & Jacobsen (2000 ▶); Chatterjee (2008 ▶); Katsuki (2004 ▶); Kim et al. (2010 ▶). For the study of active sites of enzymes in biological systems as well as in synthetic complexes of inter­est, see: Davies et al. (2004 ▶). For the preparation of bis­(pyridin-2-ylmeth­yl)amine (bpa), see: Romary et al. (1967 ▶). For structures of similar Mn complexes, see: Glerup et al. (1992 ▶); Gultneh et al. (2006 ▶).

Experimental

Crystal data

[Mn(C20H21N3)2](ClO4)2

M = 860.63

Monoclinic,

a = 23.162 (3) Å

b = 10.4755 (11) Å

c = 19.391 (2) Å

β = 118.896 (8)°

V = 4119.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 293 K

0.42 × 0.37 × 0.18 mm

Data collection

Bruker P4 diffractometer

Absorption correction: empirical (using intensity measurements) (XEMP; Siemens, 1989 ▶) T min = 0.72, T max = 0.92

4863 measured reflections

4750 independent reflections

3075 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.193

S = 1.03

4750 reflections

299 parameters

86 restraints

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.44 e Å−3

Data collection: XSCANS (Siemens, 1991 ▶); cell refinement: XSCANS; data reduction: XDISK (Siemens, 1991 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003055/mw2117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003055/mw2117Isup2.hkl

CCDC reference: 986203

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Mn(C20H21N3)2](ClO4)2	F(000) = 1788
Mr = 860.63	Dx = 1.388 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.162 (3) Å	Cell parameters from 45 reflections
b = 10.4755 (11) Å	θ = 5.0–12.5°
c = 19.391 (2) Å	µ = 0.51 mm−1
β = 118.896 (8)°	T = 293 K
V = 4119.1 (9) Å3	Plate, colorless
Z = 4	0.42 × 0.37 × 0.18 mm

Bruker P4 diffractometer	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (XEMP; Siemens, 1989)	h = 0→30
Tmin = 0.72, Tmax = 0.92	k = −13→0
4863 measured reflections	l = −25→22
4750 independent reflections	3 standard reflections every 97 reflections
3075 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0957P)2 + 3.680P] where P = (Fo2 + 2Fc2)/3
4750 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.67 e Å−3
86 restraints	Δρmin = −0.44 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mn1	0.5000	0.63686 (7)	0.7500	0.0433 (2)
N1	0.48410 (13)	0.5017 (3)	0.64439 (16)	0.0464 (6)
N1A	0.45745 (14)	0.7660 (3)	0.64777 (16)	0.0494 (7)
N1B	0.60038 (14)	0.6010 (3)	0.76090 (17)	0.0514 (7)
C1A	0.48177 (18)	0.5908 (4)	0.5841 (2)	0.0516 (8)
H1AA	0.4592	0.5495	0.5331	0.062*
H1AB	0.5265	0.6087	0.5951	0.062*
C2A	0.44771 (16)	0.7155 (3)	0.57984 (19)	0.0491 (8)
C3A	0.4120 (2)	0.7793 (4)	0.5091 (2)	0.0662 (11)
H3AA	0.4051	0.7424	0.4621	0.079*
C4A	0.3868 (2)	0.8982 (5)	0.5094 (3)	0.0752 (12)
H4AA	0.3632	0.9427	0.4625	0.090*
C5A	0.3967 (2)	0.9508 (4)	0.5788 (3)	0.0699 (11)
H5AA	0.3795	1.0307	0.5798	0.084*
C6A	0.4326 (2)	0.8826 (4)	0.6471 (2)	0.0593 (9)
H6AA	0.4399	0.9183	0.6946	0.071*
C1B	0.54401 (18)	0.4219 (4)	0.6743 (2)	0.0567 (9)
H1BA	0.5474	0.3871	0.6301	0.068*
H1BB	0.5401	0.3510	0.7040	0.068*
C2B	0.60584 (17)	0.4959 (4)	0.7263 (2)	0.0544 (9)
C3B	0.6657 (2)	0.4520 (5)	0.7378 (3)	0.0777 (13)
H3BA	0.6684	0.3778	0.7132	0.093*
C4B	0.7221 (2)	0.5204 (5)	0.7869 (3)	0.0892 (15)
H4BA	0.7634	0.4915	0.7968	0.107*
C5B	0.7161 (2)	0.6304 (5)	0.8202 (3)	0.0777 (13)
H5BA	0.7531	0.6788	0.8525	0.093*
C6B	0.65518 (18)	0.6682 (4)	0.8056 (2)	0.0614 (10)
H6BA	0.6513	0.7444	0.8277	0.074*
C1C	0.2892 (19)	0.497 (4)	0.478 (2)	0.111 (9)	0.508 (15)
H1CA	0.2539	0.5172	0.4267	0.166*	0.508 (15)
H1CB	0.3152	0.5719	0.5014	0.166*	0.508 (15)
H1CC	0.2713	0.4667	0.5106	0.166*	0.508 (15)
C2C	0.3326 (8)	0.393 (2)	0.4713 (11)	0.064 (3)	0.508 (15)
C3C	0.3123 (8)	0.334 (3)	0.3998 (12)	0.081 (4)	0.508 (15)
H3CA	0.2703	0.3510	0.3584	0.097*	0.508 (15)
C4C	0.3534 (15)	0.251 (3)	0.3883 (12)	0.076 (5)	0.508 (15)
H4CA	0.3454	0.2299	0.3378	0.092*	0.508 (15)
C5C	0.4054 (8)	0.200 (2)	0.4526 (13)	0.065 (3)	0.508 (15)
H5CA	0.4274	0.1298	0.4472	0.078*	0.508 (15)
C6C	0.4260 (7)	0.253 (2)	0.5268 (11)	0.054 (2)	0.508 (15)
H6CA	0.4635	0.2217	0.5702	0.064*	0.508 (15)
C7C	0.3917 (7)	0.352 (2)	0.5365 (10)	0.048 (3)	0.508 (15)
C8C	0.419 (3)	0.422 (7)	0.615 (2)	0.056 (6)	0.508 (15)
H8CA	0.4270	0.3585	0.6554	0.067*	0.508 (15)
H8CB	0.3852	0.4787	0.6127	0.067*	0.508 (15)
C1CA	0.3018 (19)	0.497 (5)	0.465 (2)	0.111 (9)	0.492 (15)
H1CD	0.2613	0.4931	0.4166	0.166*	0.492 (15)
H1CE	0.3217	0.5797	0.4706	0.166*	0.492 (15)
H1CF	0.2929	0.4840	0.5084	0.166*	0.492 (15)
C2CA	0.3492 (8)	0.393 (2)	0.4668 (12)	0.064 (3)	0.492 (15)
C3CA	0.3323 (9)	0.324 (3)	0.3997 (12)	0.081 (4)	0.492 (15)
H3CB	0.2963	0.3503	0.3527	0.097*	0.492 (15)
C4CA	0.3672 (16)	0.217 (3)	0.3998 (13)	0.076 (5)	0.492 (15)
H4CB	0.3501	0.1608	0.3571	0.092*	0.492 (15)
C5CA	0.4269 (8)	0.194 (2)	0.4635 (14)	0.065 (3)	0.492 (15)
H5CB	0.4558	0.1361	0.4604	0.078*	0.492 (15)
C6CA	0.4447 (7)	0.260 (2)	0.5337 (12)	0.054 (2)	0.492 (15)
H6CB	0.4823	0.2354	0.5795	0.064*	0.492 (15)
C7CA	0.4071 (8)	0.360 (2)	0.5357 (11)	0.048 (3)	0.492 (15)
C8CA	0.425 (3)	0.426 (8)	0.614 (2)	0.056 (6)	0.492 (15)
H8CC	0.3890	0.4802	0.6068	0.067*	0.492 (15)
H8CD	0.4311	0.3614	0.6525	0.067*	0.492 (15)
Cl1	0.61415 (5)	0.08236 (10)	0.72361 (6)	0.0693 (3)
O1	0.63792 (17)	0.1512 (3)	0.68050 (19)	0.0808 (12)	0.768 (4)
O2	0.65812 (17)	−0.0170 (3)	0.7645 (2)	0.0922 (15)	0.768 (4)
O3	0.55217 (15)	0.0312 (4)	0.6721 (2)	0.166 (3)	0.768 (4)
O4	0.6088 (3)	0.1638 (3)	0.7776 (2)	0.147 (2)	0.768 (4)
O1A	0.5534 (3)	0.1107 (10)	0.7195 (6)	0.0808 (12)	0.232 (4)
O2A	0.6241 (5)	−0.0500 (3)	0.7298 (7)	0.0922 (15)	0.232 (4)
O3A	0.6141 (5)	0.1268 (11)	0.6554 (4)	0.166 (3)	0.232 (4)
O4A	0.6649 (4)	0.1423 (10)	0.7898 (4)	0.147 (2)	0.232 (4)

	U11	U22	U33	U12	U13	U23
Mn1	0.0452 (4)	0.0479 (4)	0.0347 (3)	0.000	0.0175 (3)	0.000
N1	0.0470 (15)	0.0474 (16)	0.0440 (14)	−0.0036 (12)	0.0214 (12)	−0.0047 (12)
N1A	0.0570 (17)	0.0508 (17)	0.0400 (14)	0.0020 (14)	0.0232 (13)	0.0021 (12)
N1B	0.0487 (16)	0.0544 (18)	0.0507 (16)	−0.0013 (13)	0.0238 (13)	−0.0028 (13)
C1A	0.057 (2)	0.057 (2)	0.0428 (17)	−0.0020 (16)	0.0256 (16)	−0.0052 (15)
C2A	0.0493 (18)	0.056 (2)	0.0390 (16)	−0.0032 (16)	0.0191 (14)	0.0008 (15)
C3A	0.070 (2)	0.076 (3)	0.0411 (18)	0.002 (2)	0.0171 (17)	0.0087 (19)
C4A	0.073 (3)	0.078 (3)	0.058 (2)	0.007 (2)	0.018 (2)	0.023 (2)
C5A	0.071 (3)	0.057 (2)	0.072 (3)	0.008 (2)	0.026 (2)	0.012 (2)
C6A	0.071 (2)	0.050 (2)	0.057 (2)	0.0049 (18)	0.0307 (19)	0.0025 (17)
C1B	0.060 (2)	0.050 (2)	0.059 (2)	0.0060 (17)	0.0270 (18)	−0.0027 (17)
C2B	0.0505 (19)	0.052 (2)	0.060 (2)	0.0020 (16)	0.0262 (17)	0.0020 (17)
C3B	0.062 (3)	0.070 (3)	0.101 (3)	0.009 (2)	0.039 (2)	−0.008 (3)
C4B	0.053 (3)	0.086 (3)	0.123 (4)	0.005 (2)	0.038 (3)	−0.004 (3)
C5B	0.048 (2)	0.084 (3)	0.087 (3)	−0.007 (2)	0.021 (2)	−0.005 (3)
C6B	0.054 (2)	0.062 (2)	0.062 (2)	−0.0085 (18)	0.0227 (18)	−0.0058 (19)
C1C	0.056 (12)	0.133 (6)	0.098 (11)	0.008 (7)	0.002 (8)	−0.028 (7)
C2C	0.036 (7)	0.087 (3)	0.066 (3)	−0.013 (5)	0.022 (4)	−0.015 (3)
C3C	0.046 (9)	0.111 (6)	0.062 (3)	−0.017 (8)	0.007 (6)	−0.014 (3)
C4C	0.101 (12)	0.064 (14)	0.057 (5)	−0.025 (8)	0.034 (6)	−0.011 (7)
C5C	0.048 (9)	0.072 (4)	0.082 (6)	−0.028 (7)	0.039 (8)	−0.030 (4)
C6C	0.035 (7)	0.056 (3)	0.070 (4)	−0.022 (6)	0.026 (5)	−0.014 (3)
C7C	0.034 (6)	0.061 (3)	0.053 (2)	−0.025 (5)	0.025 (4)	−0.011 (2)
C8C	0.055 (9)	0.061 (4)	0.052 (2)	−0.011 (6)	0.026 (3)	−0.015 (3)
C1CA	0.056 (12)	0.133 (6)	0.098 (11)	0.008 (7)	0.002 (8)	−0.028 (7)
C2CA	0.036 (7)	0.087 (3)	0.066 (3)	−0.013 (5)	0.022 (4)	−0.015 (3)
C3CA	0.046 (9)	0.111 (6)	0.062 (3)	−0.017 (8)	0.007 (6)	−0.014 (3)
C4CA	0.101 (12)	0.064 (14)	0.057 (5)	−0.025 (8)	0.034 (6)	−0.011 (7)
C5CA	0.048 (9)	0.072 (4)	0.082 (6)	−0.028 (7)	0.039 (8)	−0.030 (4)
C6CA	0.035 (7)	0.056 (3)	0.070 (4)	−0.022 (6)	0.026 (5)	−0.014 (3)
C7CA	0.034 (6)	0.061 (3)	0.053 (2)	−0.025 (5)	0.025 (4)	−0.011 (2)
C8CA	0.055 (9)	0.061 (4)	0.052 (2)	−0.011 (6)	0.026 (3)	−0.015 (3)
Cl1	0.0697 (7)	0.0699 (7)	0.0733 (7)	0.0084 (5)	0.0386 (5)	0.0158 (5)
O1	0.112 (3)	0.072 (2)	0.083 (2)	0.006 (2)	0.066 (2)	0.0191 (19)
O2	0.101 (3)	0.078 (3)	0.098 (3)	0.022 (2)	0.048 (3)	0.028 (2)
O3	0.110 (4)	0.196 (6)	0.154 (5)	−0.040 (4)	0.033 (3)	0.002 (4)
O4	0.232 (6)	0.129 (4)	0.126 (4)	0.051 (4)	0.125 (4)	0.009 (3)
O1A	0.112 (3)	0.072 (2)	0.083 (2)	0.006 (2)	0.066 (2)	0.0191 (19)
O2A	0.101 (3)	0.078 (3)	0.098 (3)	0.022 (2)	0.048 (3)	0.028 (2)
O3A	0.110 (4)	0.196 (6)	0.154 (5)	−0.040 (4)	0.033 (3)	0.002 (4)
O4A	0.232 (6)	0.129 (4)	0.126 (4)	0.051 (4)	0.125 (4)	0.009 (3)

Mn1—N1Ai	2.201 (3)	C1C—H1CA	0.9600
Mn1—N1A	2.201 (3)	C1C—H1CB	0.9600
Mn1—N1B	2.262 (3)	C1C—H1CC	0.9600
Mn1—N1Bi	2.262 (3)	C2C—C3C	1.376 (12)
Mn1—N1i	2.367 (3)	C2C—C7C	1.408 (11)
Mn1—N1	2.367 (3)	C3C—C4C	1.390 (15)
N1—C8CA	1.43 (9)	C3C—H3CA	0.9300
N1—C1A	1.476 (4)	C4C—C5C	1.354 (14)
N1—C1B	1.478 (4)	C4C—H4CA	0.9300
N1—C8C	1.57 (9)	C5C—C6C	1.396 (11)
N1A—C2A	1.334 (4)	C5C—H5CA	0.9300
N1A—C6A	1.347 (5)	C6C—C7C	1.373 (11)
N1B—C2B	1.327 (5)	C6C—H6CA	0.9300
N1B—C6B	1.340 (5)	C7C—C8C	1.526 (12)
C1A—C2A	1.507 (5)	C8C—H8CA	0.9700
C1A—H1AA	0.9700	C8C—H8CB	0.9700
C1A—H1AB	0.9700	C1CA—C2CA	1.536 (12)
C2A—C3A	1.384 (5)	C1CA—H1CD	0.9600
C3A—C4A	1.376 (6)	C1CA—H1CE	0.9600
C3A—H3AA	0.9300	C1CA—H1CF	0.9600
C4A—C5A	1.367 (6)	C2CA—C3CA	1.371 (12)
C4A—H4AA	0.9300	C2CA—C7CA	1.406 (11)
C5A—C6A	1.375 (5)	C3CA—C4CA	1.388 (15)
C5A—H5AA	0.9300	C3CA—H3CB	0.9300
C6A—H6AA	0.9300	C4CA—C5CA	1.357 (14)
C1B—C2B	1.507 (5)	C4CA—H4CB	0.9300
C1B—H1BA	0.9700	C5CA—C6CA	1.397 (11)
C1B—H1BB	0.9700	C5CA—H5CB	0.9300
C2B—C3B	1.373 (5)	C6CA—C7CA	1.376 (11)
C3B—C4B	1.387 (6)	C6CA—H6CB	0.9300
C3B—H3BA	0.9300	C7CA—C8CA	1.527 (12)
C4B—C5B	1.361 (7)	C8CA—H8CC	0.9700
C4B—H4BA	0.9300	C8CA—H8CD	0.9700
C5B—C6B	1.358 (6)	Cl1—O2A	1.401 (2)
C5B—H5BA	0.9300	Cl1—O3A	1.401 (2)
C6B—H6BA	0.9300	Cl1—O4A	1.402 (2)
C1C—C2C	1.528 (12)	Cl1—O1A	1.402 (2)
N1Ai—Mn1—N1A	104.11 (15)	N1B—C6B—C5B	123.1 (4)
N1Ai—Mn1—N1B	91.45 (11)	N1B—C6B—H6BA	118.5
N1A—Mn1—N1B	100.32 (11)	C5B—C6B—H6BA	118.5
N1Ai—Mn1—N1Bi	100.32 (11)	C2C—C1C—H1CA	109.5
N1A—Mn1—N1Bi	91.44 (11)	C2C—C1C—H1CB	109.5
N1B—Mn1—N1Bi	160.87 (16)	H1CA—C1C—H1CB	109.5
N1Ai—Mn1—N1i	76.92 (10)	C2C—C1C—H1CC	109.5
N1A—Mn1—N1i	164.06 (10)	H1CA—C1C—H1CC	109.5
N1B—Mn1—N1i	95.54 (10)	H1CB—C1C—H1CC	109.5
N1Bi—Mn1—N1i	72.83 (10)	C3C—C2C—C7C	118.7 (11)
N1Ai—Mn1—N1	164.06 (10)	C3C—C2C—C1C	119.1 (13)
N1A—Mn1—N1	76.92 (10)	C7C—C2C—C1C	122.2 (13)
N1B—Mn1—N1	72.83 (10)	C2C—C3C—C4C	121.1 (12)
N1Bi—Mn1—N1	95.54 (10)	C2C—C3C—H3CA	119.4
N1i—Mn1—N1	106.56 (14)	C4C—C3C—H3CA	119.4
C8CA—N1—C1A	111 (3)	C5C—C4C—C3C	118.3 (16)
C8CA—N1—C1B	112 (2)	C5C—C4C—H4CA	120.9
C1A—N1—C1B	109.7 (3)	C3C—C4C—H4CA	120.9
C1A—N1—C8C	113 (2)	C4C—C5C—C6C	120.1 (13)
C1B—N1—C8C	113.2 (18)	C4C—C5C—H5CA	120.0
C8CA—N1—Mn1	114.1 (17)	C6C—C5C—H5CA	120.0
C1A—N1—Mn1	103.7 (2)	C7C—C6C—C5C	120.7 (12)
C1B—N1—Mn1	105.9 (2)	C7C—C6C—H6CA	119.6
C8C—N1—Mn1	110.6 (14)	C5C—C6C—H6CA	119.6
C2A—N1A—C6A	118.9 (3)	C6C—C7C—C2C	118.8 (11)
C2A—N1A—Mn1	115.7 (2)	C6C—C7C—C8C	120.4 (13)
C6A—N1A—Mn1	124.7 (2)	C2C—C7C—C8C	120.6 (14)
C2B—N1B—C6B	118.1 (3)	C7C—C8C—N1	119 (5)
C2B—N1B—Mn1	115.8 (2)	C7C—C8C—H8CA	107.7
C6B—N1B—Mn1	125.6 (3)	N1—C8C—H8CA	107.7
N1—C1A—C2A	114.2 (3)	C7C—C8C—H8CB	107.7
N1—C1A—H1AA	108.7	N1—C8C—H8CB	107.7
C2A—C1A—H1AA	108.7	H8CA—C8C—H8CB	107.1
N1—C1A—H1AB	108.7	C2CA—C1CA—H1CD	109.5
C2A—C1A—H1AB	108.7	C2CA—C1CA—H1CE	109.5
H1AA—C1A—H1AB	107.6	H1CD—C1CA—H1CE	109.5
N1A—C2A—C3A	121.4 (4)	C2CA—C1CA—H1CF	109.5
N1A—C2A—C1A	117.1 (3)	H1CD—C1CA—H1CF	109.5
C3A—C2A—C1A	121.3 (3)	H1CE—C1CA—H1CF	109.5
C4A—C3A—C2A	119.0 (4)	C3CA—C2CA—C7CA	118.3 (12)
C4A—C3A—H3AA	120.5	C3CA—C2CA—C1CA	119.0 (14)
C2A—C3A—H3AA	120.5	C7CA—C2CA—C1CA	122.6 (14)
C5A—C4A—C3A	120.0 (4)	C2CA—C3CA—C4CA	122.0 (14)
C5A—C4A—H4AA	120.0	C2CA—C3CA—H3CB	119.0
C3A—C4A—H4AA	120.0	C4CA—C3CA—H3CB	119.0
C4A—C5A—C6A	118.3 (4)	C5CA—C4CA—C3CA	118.5 (16)
C4A—C5A—H5AA	120.9	C5CA—C4CA—H4CB	120.7
C6A—C5A—H5AA	120.9	C3CA—C4CA—H4CB	120.7
N1A—C6A—C5A	122.5 (4)	C4CA—C5CA—C6CA	119.6 (13)
N1A—C6A—H6AA	118.8	C4CA—C5CA—H5CB	120.2
C5A—C6A—H6AA	118.8	C6CA—C5CA—H5CB	120.2
N1—C1B—C2B	112.3 (3)	C7CA—C6CA—C5CA	120.6 (12)
N1—C1B—H1BA	109.1	C7CA—C6CA—H6CB	119.7
C2B—C1B—H1BA	109.1	C5CA—C6CA—H6CB	119.7
N1—C1B—H1BB	109.1	C6CA—C7CA—C2CA	119.3 (11)
C2B—C1B—H1BB	109.1	C6CA—C7CA—C8CA	119.8 (15)
H1BA—C1B—H1BB	107.9	C2CA—C7CA—C8CA	120.7 (14)
N1B—C2B—C3B	122.1 (4)	N1—C8CA—C7CA	114 (6)
N1B—C2B—C1B	118.2 (3)	N1—C8CA—H8CC	108.6
C3B—C2B—C1B	119.7 (4)	C7CA—C8CA—H8CC	108.6
C2B—C3B—C4B	118.8 (4)	N1—C8CA—H8CD	108.6
C2B—C3B—H3BA	120.6	C7CA—C8CA—H8CD	108.6
C4B—C3B—H3BA	120.6	H8CC—C8CA—H8CD	109.0
C5B—C4B—C3B	119.0 (4)	O2A—Cl1—O3A	109.53 (9)
C5B—C4B—H4BA	120.5	O2A—Cl1—O4A	109.54 (9)
C3B—C4B—H4BA	120.5	O3A—Cl1—O4A	109.50 (9)
C6B—C5B—C4B	118.8 (4)	O2A—Cl1—O1A	109.45 (9)
C6B—C5B—H5BA	120.6	O3A—Cl1—O1A	109.42 (9)
C4B—C5B—H5BA	120.6	O4A—Cl1—O1A	109.38 (9)
C8CA—N1—C1A—C2A	86.2 (15)	C4B—C5B—C6B—N1B	1.3 (7)
C1B—N1—C1A—C2A	−149.7 (3)	C7C—C2C—C3C—C4C	−10 (4)
C8C—N1—C1A—C2A	83.0 (13)	C1C—C2C—C3C—C4C	172 (4)
Mn1—N1—C1A—C2A	−36.8 (3)	C2C—C3C—C4C—C5C	18 (5)
C6A—N1A—C2A—C3A	−0.9 (5)	C3C—C4C—C5C—C6C	−15 (5)
Mn1—N1A—C2A—C3A	169.7 (3)	C4C—C5C—C6C—C7C	4 (4)
C6A—N1A—C2A—C1A	174.3 (3)	C5C—C6C—C7C—C2C	4 (3)
Mn1—N1A—C2A—C1A	−15.1 (4)	C5C—C6C—C7C—C8C	−172 (5)
N1—C1A—C2A—N1A	37.9 (4)	C3C—C2C—C7C—C6C	−2 (3)
N1—C1A—C2A—C3A	−146.9 (3)	C1C—C2C—C7C—C6C	176 (3)
N1A—C2A—C3A—C4A	0.9 (6)	C3C—C2C—C7C—C8C	175 (5)
C1A—C2A—C3A—C4A	−174.2 (4)	C1C—C2C—C7C—C8C	−7 (6)
C2A—C3A—C4A—C5A	−0.8 (7)	C6C—C7C—C8C—N1	66 (6)
C3A—C4A—C5A—C6A	0.7 (7)	C2C—C7C—C8C—N1	−110 (3)
C2A—N1A—C6A—C5A	0.9 (6)	C1A—N1—C8C—C7C	50 (4)
Mn1—N1A—C6A—C5A	−168.8 (3)	C1B—N1—C8C—C7C	−75 (4)
C4A—C5A—C6A—N1A	−0.8 (7)	Mn1—N1—C8C—C7C	166 (3)
C8CA—N1—C1B—C2B	−164 (3)	C7CA—C2CA—C3CA—C4CA	6 (4)
C1A—N1—C1B—C2B	72.3 (4)	C1CA—C2CA—C3CA—C4CA	−170 (4)
C8C—N1—C1B—C2B	−160 (2)	C2CA—C3CA—C4CA—C5CA	−14 (6)
Mn1—N1—C1B—C2B	−39.1 (3)	C3CA—C4CA—C5CA—C6CA	15 (5)
C6B—N1B—C2B—C3B	3.0 (6)	C4CA—C5CA—C6CA—C7CA	−10 (4)
Mn1—N1B—C2B—C3B	−170.1 (3)	C5CA—C6CA—C7CA—C2CA	2 (3)
C6B—N1B—C2B—C1B	−178.5 (3)	C5CA—C6CA—C7CA—C8CA	177 (5)
Mn1—N1B—C2B—C1B	8.5 (4)	C3CA—C2CA—C7CA—C6CA	0 (3)
N1—C1B—C2B—N1B	22.8 (5)	C1CA—C2CA—C7CA—C6CA	175 (3)
N1—C1B—C2B—C3B	−158.6 (4)	C3CA—C2CA—C7CA—C8CA	−175 (5)
N1B—C2B—C3B—C4B	−0.4 (7)	C1CA—C2CA—C7CA—C8CA	1 (6)
C1B—C2B—C3B—C4B	−178.9 (4)	C1A—N1—C8CA—C7CA	51 (4)
C2B—C3B—C4B—C5B	−1.8 (8)	C1B—N1—C8CA—C7CA	−72 (4)
C3B—C4B—C5B—C6B	1.3 (8)	Mn1—N1—C8CA—C7CA	168 (2)
C2B—N1B—C6B—C5B	−3.5 (6)	C6CA—C7CA—C8CA—N1	71 (6)
Mn1—N1B—C6B—C5B	168.8 (3)	C2CA—C7CA—C8CA—N1	−114 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3AA···O3Aii	0.93	2.51	3.106 (5)	122
C6A—H6AA···Cl1iii	0.93	2.99	3.802 (4)	146
C6A—H6AA···O1Aiii	0.93	2.57	3.420 (10)	152
C6A—H6AA···O2Aiii	0.93	2.56	3.309 (12)	138
C1B—H1BB···O4	0.97	2.49	3.266 (5)	136
C1B—H1BB···O1A	0.97	2.54	3.356 (11)	142
C3B—H3BA···O1	0.93	2.47	3.300 (6)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3A—H3AA⋯O3A i	0.93	2.51	3.106 (5)	122
C6A—H6AA⋯O1A ii	0.93	2.57	3.420 (10)	152
C6A—H6AA⋯O2A ii	0.93	2.56	3.309 (12)	138
C1B—H1BB⋯O4	0.97	2.49	3.266 (5)	136
C1B—H1BB⋯O1A	0.97	2.54	3.356 (11)	142
C3B—H3BA⋯O1	0.93	2.47	3.300 (6)	149

Symmetry codes: (i) ; (ii) .