Hexa-kis-(1-benzyl-1H-imidazole-κN)manganese(II) bis-(perchlorate).

In the title compound, [Mn(C(10)H(10)N(2))(6)](ClO(4))(2), the Mn(II) ion, located on an inversion center, is coordinated by six N atoms from three pairs of symmetry-related 1-benzyl-1H-imidazole ligands in a distorted octa-hedral geometry. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the complex cations and perchlorate anions.

Related literature

For background to the coordination chemistry of imidazole and its derivatives, see: Cui et al. (2005 ▶); Fan et al. (2005 ▶); Li et al. (2009 ▶); Peng et al. (2010 ▶); Santoro et al. (2000 ▶). For the synthesis of 1-benzyl-1H-imidazole, see: Shen et al. (2010 ▶).

Experimental

Crystal data

[Mn(C10H10N2)6](ClO4)2

M = 1203.04

Triclinic,

a = 9.2832 (19) Å

b = 12.744 (3) Å

c = 13.317 (3) Å

α = 84.55 (3)°

β = 79.56 (3)°

γ = 75.87 (3)°

V = 1500.4 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.37 mm−1

T = 295 K

0.28 × 0.27 × 0.26 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.796, T max = 0.808

15862 measured reflections

6832 independent reflections

5066 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.188

S = 0.84

6832 reflections

376 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.62 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811023531/hy2441sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023531/hy2441Isup2.hkl

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

[Mn(C10H10N2)6](ClO4)2	Z = 1
Mr = 1203.04	F(000) = 627
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2832 (19) Å	Cell parameters from 4812 reflections
b = 12.744 (3) Å	θ = 4.6–22.4°
c = 13.317 (3) Å	µ = 0.37 mm−1
α = 84.55 (3)°	T = 295 K
β = 79.56 (3)°	Block, yellow
γ = 75.87 (3)°	0.28 × 0.27 × 0.26 mm
V = 1500.4 (6) Å3

Bruker APEX CCD diffractometer	6832 independent reflections
Radiation source: fine-focus sealed tube	5066 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.796, Tmax = 0.808	k = −16→16
15862 measured reflections	l = −17→17

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 0.84	w = 1/[σ2(Fo2) + (0.1228P)2 + 1.5062P] where P = (Fo2 + 2Fc2)/3
6832 reflections	(Δ/σ)max < 0.001
376 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

	x	y	z	Uiso*/Ueq
Mn1	1.0000	0.5000	0.0000	0.02471 (16)
N3	0.9796 (3)	0.35883 (19)	−0.06887 (19)	0.0422 (6)
N1	1.1493 (3)	0.39905 (19)	0.09564 (18)	0.0412 (5)
N5	0.8035 (3)	0.4910 (2)	0.11543 (19)	0.0455 (6)
N2	1.2826 (3)	0.2585 (2)	0.1725 (2)	0.0477 (6)
N4	0.9231 (3)	0.2058 (2)	−0.0898 (2)	0.0540 (7)
N6	0.6644 (3)	0.4632 (2)	0.2627 (2)	0.0558 (7)
C11	0.7996 (4)	0.4368 (3)	0.2039 (2)	0.0530 (8)
H11A	0.8813	0.3859	0.2237	0.064*
C1	1.1700 (3)	0.2942 (2)	0.1194 (2)	0.0429 (6)
H1A	1.1128	0.2505	0.1014	0.051*
C21	0.8943 (4)	0.2915 (2)	−0.0328 (2)	0.0470 (7)
H21A	0.8219	0.3022	0.0258	0.056*
C5	1.2858 (4)	0.1390 (3)	0.3294 (3)	0.0535 (8)
C4	1.3311 (4)	0.1481 (3)	0.2159 (3)	0.0581 (9)
H4A	1.4399	0.1249	0.1992	0.070*
H4B	1.2880	0.0997	0.1849	0.070*
C2	1.2564 (4)	0.4302 (3)	0.1362 (3)	0.0561 (8)
H2A	1.2699	0.5005	0.1320	0.067*
C25	0.7194 (5)	0.1279 (3)	−0.1260 (3)	0.0606 (9)
C3	1.3391 (4)	0.3448 (3)	0.1830 (3)	0.0605 (9)
H3A	1.4192	0.3448	0.2161	0.073*
C22	1.0651 (4)	0.3146 (3)	−0.1548 (3)	0.0706 (11)
H22A	1.1367	0.3447	−0.1981	0.085*
C15	0.6994 (5)	0.4471 (3)	0.4434 (3)	0.0681 (11)
C14	0.6202 (5)	0.4179 (4)	0.3652 (3)	0.0761 (12)
H14A	0.6417	0.3396	0.3635	0.091*
H14B	0.5124	0.4437	0.3856	0.091*
C12	0.6625 (4)	0.5563 (3)	0.1181 (3)	0.0623 (9)
H12A	0.6305	0.6048	0.0654	0.075*
C23	1.0310 (5)	0.2205 (4)	−0.1686 (4)	0.0799 (14)
H23A	1.0736	0.1748	−0.2219	0.096*
C13	0.5767 (4)	0.5398 (4)	0.2083 (3)	0.0712 (11)
H13A	0.4766	0.5743	0.2293	0.085*
C17	0.7849 (6)	0.5760 (6)	0.5238 (5)	0.1018 (18)
H17A	0.7962	0.6461	0.5272	0.122*
C24	0.8506 (5)	0.1142 (3)	−0.0708 (3)	0.0695 (11)
H24A	0.8163	0.1052	0.0020	0.083*
H24B	0.9245	0.0487	−0.0919	0.083*
C20	0.7495 (7)	0.3705 (5)	0.5150 (4)	0.1027 (17)
H20A	0.7380	0.3004	0.5128	0.123*
C27	0.6155 (7)	0.1387 (5)	−0.2792 (4)	0.0995 (17)
H27A	0.6293	0.1409	−0.3502	0.119*
C29	0.4569 (6)	0.1404 (5)	−0.1228 (6)	0.115 (2)
H29A	0.3617	0.1422	−0.0851	0.138*
C26	0.7371 (6)	0.1290 (4)	−0.2298 (4)	0.0850 (13)
H26A	0.8328	0.1233	−0.2681	0.102*
C10	1.1399 (5)	0.1396 (4)	0.3710 (4)	0.0858 (13)
H10A	1.0682	0.1489	0.3284	0.103*
C6	1.3894 (5)	0.1264 (4)	0.3928 (3)	0.0857 (14)
H6A	1.4888	0.1274	0.3660	0.103*
C18	0.8349 (7)	0.4956 (8)	0.5945 (5)	0.121 (2)
H18A	0.8817	0.5106	0.6457	0.145*
C28	0.4775 (7)	0.1447 (4)	−0.2246 (6)	0.0987 (17)
H28A	0.3957	0.1520	−0.2581	0.118*
C9	1.0982 (9)	0.1267 (5)	0.4738 (5)	0.124 (2)
H9A	0.9982	0.1284	0.5013	0.149*
C7	1.3462 (9)	0.1120 (6)	0.4965 (4)	0.134 (3)
H7A	1.4173	0.1026	0.5397	0.161*
C16	0.7176 (5)	0.5507 (4)	0.4475 (3)	0.0757 (12)
H16A	0.6844	0.6040	0.3988	0.091*
C30	0.5782 (6)	0.1331 (4)	−0.0734 (4)	0.0963 (16)
H30A	0.5628	0.1318	−0.0024	0.116*
C8	1.2031 (11)	0.1114 (5)	0.5363 (5)	0.139 (3)
H8A	1.1756	0.1006	0.6065	0.167*
C19	0.8155 (9)	0.3944 (8)	0.5892 (6)	0.132 (3)
H19A	0.8484	0.3405	0.6376	0.159*
Cl1	0.79576 (10)	0.12692 (7)	0.22679 (7)	0.0580 (2)
O1	0.9416 (3)	0.1287 (3)	0.1713 (2)	0.0833 (9)
O3	0.6900 (3)	0.2104 (3)	0.1833 (3)	0.0930 (10)
O4	0.7860 (4)	0.1465 (3)	0.3315 (3)	0.1030 (11)
O2	0.7630 (4)	0.0272 (3)	0.2180 (3)	0.1076 (12)

	U11	U22	U33	U12	U13	U23
Mn1	0.0268 (3)	0.0249 (3)	0.0220 (3)	−0.00701 (19)	−0.00161 (19)	−0.00076 (18)
N3	0.0437 (13)	0.0387 (13)	0.0442 (13)	−0.0072 (10)	−0.0073 (11)	−0.0077 (10)
N1	0.0440 (13)	0.0419 (13)	0.0386 (12)	−0.0113 (10)	−0.0092 (10)	0.0017 (10)
N5	0.0448 (14)	0.0474 (14)	0.0433 (14)	−0.0153 (11)	0.0038 (11)	−0.0063 (11)
N2	0.0529 (15)	0.0432 (14)	0.0461 (14)	−0.0068 (11)	−0.0154 (12)	0.0042 (11)
N4	0.0567 (16)	0.0424 (14)	0.0689 (18)	−0.0108 (12)	−0.0206 (14)	−0.0142 (13)
N6	0.0570 (17)	0.0605 (17)	0.0476 (15)	−0.0247 (14)	0.0190 (13)	−0.0155 (13)
C11	0.0571 (19)	0.0523 (18)	0.0439 (17)	−0.0162 (15)	0.0123 (15)	−0.0041 (14)
C1	0.0465 (16)	0.0396 (15)	0.0440 (16)	−0.0131 (12)	−0.0094 (13)	0.0019 (12)
C21	0.0607 (19)	0.0396 (15)	0.0444 (16)	−0.0158 (14)	−0.0116 (14)	−0.0047 (13)
C5	0.061 (2)	0.0446 (17)	0.0525 (19)	−0.0051 (15)	−0.0179 (16)	0.0088 (14)
C4	0.073 (2)	0.0418 (17)	0.0540 (19)	−0.0006 (16)	−0.0169 (17)	0.0063 (14)
C2	0.068 (2)	0.0441 (17)	0.064 (2)	−0.0168 (15)	−0.0312 (18)	0.0044 (15)
C25	0.072 (2)	0.0407 (17)	0.078 (3)	−0.0212 (16)	−0.020 (2)	−0.0092 (17)
C3	0.067 (2)	0.0539 (19)	0.070 (2)	−0.0156 (17)	−0.0364 (19)	0.0025 (17)
C22	0.058 (2)	0.085 (3)	0.074 (2)	−0.030 (2)	0.0125 (19)	−0.042 (2)
C15	0.070 (2)	0.072 (2)	0.051 (2)	−0.017 (2)	0.0224 (18)	−0.0111 (18)
C14	0.090 (3)	0.083 (3)	0.053 (2)	−0.042 (2)	0.031 (2)	−0.015 (2)
C12	0.0468 (19)	0.075 (2)	0.059 (2)	−0.0089 (17)	−0.0002 (16)	−0.0042 (18)
C23	0.061 (2)	0.091 (3)	0.094 (3)	−0.027 (2)	0.013 (2)	−0.062 (3)
C13	0.0459 (19)	0.088 (3)	0.071 (3)	−0.0093 (19)	0.0129 (18)	−0.022 (2)
C17	0.083 (3)	0.130 (5)	0.096 (4)	−0.038 (3)	0.016 (3)	−0.046 (4)
C24	0.090 (3)	0.0420 (18)	0.089 (3)	−0.0231 (18)	−0.038 (2)	−0.0039 (18)
C20	0.113 (4)	0.096 (4)	0.080 (3)	−0.004 (3)	0.000 (3)	0.007 (3)
C27	0.128 (5)	0.104 (4)	0.093 (4)	−0.057 (4)	−0.052 (3)	0.007 (3)
C29	0.064 (3)	0.133 (5)	0.147 (6)	−0.014 (3)	−0.009 (4)	−0.039 (4)
C26	0.085 (3)	0.103 (4)	0.085 (3)	−0.049 (3)	−0.026 (3)	0.006 (3)
C10	0.072 (3)	0.092 (3)	0.092 (3)	−0.025 (2)	−0.005 (2)	0.004 (3)
C6	0.074 (3)	0.105 (4)	0.067 (3)	0.010 (2)	−0.030 (2)	0.000 (2)
C18	0.073 (3)	0.204 (8)	0.075 (4)	−0.011 (5)	−0.002 (3)	−0.034 (5)
C28	0.081 (3)	0.076 (3)	0.151 (6)	−0.018 (3)	−0.052 (4)	−0.009 (3)
C9	0.129 (5)	0.105 (4)	0.109 (5)	−0.022 (4)	0.041 (4)	0.014 (4)
C7	0.149 (6)	0.156 (6)	0.066 (3)	0.046 (5)	−0.051 (4)	−0.006 (3)
C16	0.085 (3)	0.076 (3)	0.064 (2)	−0.027 (2)	0.010 (2)	−0.016 (2)
C30	0.086 (3)	0.105 (4)	0.098 (4)	−0.018 (3)	−0.006 (3)	−0.038 (3)
C8	0.188 (8)	0.111 (5)	0.061 (3)	0.034 (5)	0.017 (4)	0.028 (3)
C19	0.126 (6)	0.150 (7)	0.096 (5)	0.005 (5)	−0.015 (4)	0.009 (5)
Cl1	0.0584 (5)	0.0493 (5)	0.0669 (5)	−0.0173 (4)	−0.0080 (4)	0.0016 (4)
O1	0.0582 (16)	0.100 (2)	0.091 (2)	−0.0260 (16)	−0.0023 (15)	0.0013 (18)
O3	0.0729 (19)	0.084 (2)	0.107 (2)	0.0009 (16)	−0.0150 (18)	0.0226 (18)
O4	0.105 (3)	0.133 (3)	0.073 (2)	−0.028 (2)	−0.0112 (19)	−0.020 (2)
O2	0.127 (3)	0.0634 (19)	0.142 (3)	−0.047 (2)	−0.009 (3)	−0.010 (2)

Mn1—N1	2.158 (2)	C14—H14B	0.9700
Mn1—N3	2.158 (2)	C12—C13	1.346 (5)
Mn1—N5	2.181 (2)	C12—H12A	0.9300
N3—C21	1.307 (4)	C23—H23A	0.9300
N3—C22	1.353 (4)	C13—H13A	0.9300
N1—C1	1.319 (4)	C17—C18	1.376 (9)
N1—C2	1.366 (4)	C17—C16	1.384 (7)
N5—C11	1.307 (4)	C17—H17A	0.9300
N5—C12	1.366 (4)	C24—H24A	0.9700
N2—C1	1.332 (4)	C24—H24B	0.9700
N2—C3	1.358 (4)	C20—C19	1.346 (10)
N2—C4	1.465 (4)	C20—H20A	0.9300
N4—C21	1.336 (4)	C27—C28	1.342 (8)
N4—C23	1.346 (5)	C27—C26	1.382 (7)
N4—C24	1.464 (4)	C27—H27A	0.9300
N6—C11	1.338 (4)	C29—C28	1.333 (9)
N6—C13	1.353 (5)	C29—C30	1.384 (8)
N6—C14	1.458 (4)	C29—H29A	0.9300
C11—H11A	0.9300	C26—H26A	0.9300
C1—H1A	0.9300	C10—C9	1.359 (8)
C21—H21A	0.9300	C10—H10A	0.9300
C5—C6	1.362 (5)	C6—C7	1.375 (7)
C5—C10	1.366 (6)	C6—H6A	0.9300
C5—C4	1.495 (5)	C18—C19	1.355 (10)
C4—H4A	0.9700	C18—H18A	0.9300
C4—H4B	0.9700	C28—H28A	0.9300
C2—C3	1.341 (5)	C9—C8	1.361 (11)
C2—H2A	0.9300	C9—H9A	0.9300
C25—C30	1.358 (6)	C7—C8	1.339 (10)
C25—C26	1.361 (6)	C7—H7A	0.9300
C25—C24	1.501 (5)	C16—H16A	0.9300
C3—H3A	0.9300	C30—H30A	0.9300
C22—C23	1.349 (5)	C8—H8A	0.9300
C22—H22A	0.9300	C19—H19A	0.9300
C15—C20	1.356 (7)	Cl1—O2	1.397 (3)
C15—C16	1.379 (6)	Cl1—O3	1.418 (3)
C15—C14	1.500 (6)	Cl1—O4	1.422 (3)
C14—H14A	0.9700	Cl1—O1	1.424 (3)
N1—Mn1—N1i	180.000 (1)	N6—C14—H14B	109.0
N1—Mn1—N3i	89.45 (9)	C15—C14—H14B	109.0
N1i—Mn1—N3i	90.55 (9)	H14A—C14—H14B	107.8
N1—Mn1—N3	90.55 (9)	C13—C12—N5	109.7 (4)
N1i—Mn1—N3	89.45 (9)	C13—C12—H12A	125.2
N3i—Mn1—N3	180.00 (12)	N5—C12—H12A	125.2
N1—Mn1—N5	91.52 (10)	N4—C23—C22	106.5 (3)
N1i—Mn1—N5	88.48 (10)	N4—C23—H23A	126.8
N3i—Mn1—N5	89.34 (10)	C22—C23—H23A	126.8
N3—Mn1—N5	90.66 (10)	C12—C13—N6	106.7 (3)
N1—Mn1—N5i	88.48 (10)	C12—C13—H13A	126.6
N1i—Mn1—N5i	91.52 (10)	N6—C13—H13A	126.6
N3i—Mn1—N5i	90.66 (10)	C18—C17—C16	118.8 (6)
N3—Mn1—N5i	89.34 (10)	C18—C17—H17A	120.6
N5—Mn1—N5i	180.00 (14)	C16—C17—H17A	120.6
C21—N3—C22	104.8 (3)	N4—C24—C25	113.3 (3)
C21—N3—Mn1	128.3 (2)	N4—C24—H24A	108.9
C22—N3—Mn1	126.6 (2)	C25—C24—H24A	108.9
C1—N1—C2	104.6 (3)	N4—C24—H24B	108.9
C1—N1—Mn1	129.2 (2)	C25—C24—H24B	108.9
C2—N1—Mn1	125.8 (2)	H24A—C24—H24B	107.7
C11—N5—C12	105.0 (3)	C19—C20—C15	121.2 (7)
C11—N5—Mn1	127.9 (2)	C19—C20—H20A	119.4
C12—N5—Mn1	126.2 (2)	C15—C20—H20A	119.4
C1—N2—C3	107.1 (3)	C28—C27—C26	119.9 (5)
C1—N2—C4	126.4 (3)	C28—C27—H27A	120.0
C3—N2—C4	126.4 (3)	C26—C27—H27A	120.0
C21—N4—C23	106.5 (3)	C28—C29—C30	119.5 (6)
C21—N4—C24	126.7 (3)	C28—C29—H29A	120.3
C23—N4—C24	126.8 (3)	C30—C29—H29A	120.3
C11—N6—C13	106.5 (3)	C25—C26—C27	121.1 (5)
C11—N6—C14	126.6 (4)	C25—C26—H26A	119.4
C13—N6—C14	126.8 (3)	C27—C26—H26A	119.4
N5—C11—N6	112.1 (3)	C9—C10—C5	120.9 (6)
N5—C11—H11A	124.0	C9—C10—H10A	119.5
N6—C11—H11A	124.0	C5—C10—H10A	119.5
N1—C1—N2	111.8 (3)	C5—C6—C7	119.7 (5)
N1—C1—H1A	124.1	C5—C6—H6A	120.2
N2—C1—H1A	124.1	C7—C6—H6A	120.2
N3—C21—N4	112.2 (3)	C19—C18—C17	119.8 (7)
N3—C21—H21A	123.9	C19—C18—H18A	120.1
N4—C21—H21A	123.9	C17—C18—H18A	120.1
C6—C5—C10	118.9 (4)	C29—C28—C27	120.5 (5)
C6—C5—C4	120.9 (4)	C29—C28—H28A	119.8
C10—C5—C4	120.2 (4)	C27—C28—H28A	119.8
N2—C4—C5	112.9 (3)	C10—C9—C8	119.8 (6)
N2—C4—H4A	109.0	C10—C9—H9A	120.1
C5—C4—H4A	109.0	C8—C9—H9A	120.1
N2—C4—H4B	109.0	C8—C7—C6	120.8 (6)
C5—C4—H4B	109.0	C8—C7—H7A	119.6
H4A—C4—H4B	107.8	C6—C7—H7A	119.6
C3—C2—N1	110.3 (3)	C15—C16—C17	120.5 (5)
C3—C2—H2A	124.9	C15—C16—H16A	119.8
N1—C2—H2A	124.9	C17—C16—H16A	119.8
C30—C25—C26	117.2 (4)	C25—C30—C29	121.8 (5)
C30—C25—C24	120.8 (4)	C25—C30—H30A	119.1
C26—C25—C24	121.9 (4)	C29—C30—H30A	119.1
C2—C3—N2	106.3 (3)	C7—C8—C9	119.9 (5)
C2—C3—H3A	126.9	C7—C8—H8A	120.1
N2—C3—H3A	126.9	C9—C8—H8A	120.1
C23—C22—N3	110.0 (3)	C20—C19—C18	121.1 (7)
C23—C22—H22A	125.0	C20—C19—H19A	119.5
N3—C22—H22A	125.0	C18—C19—H19A	119.5
C20—C15—C16	118.7 (5)	O2—Cl1—O3	109.1 (2)
C20—C15—C14	119.2 (5)	O2—Cl1—O4	110.3 (2)
C16—C15—C14	122.1 (4)	O3—Cl1—O4	108.7 (2)
N6—C14—C15	113.1 (3)	O2—Cl1—O1	109.8 (2)
N6—C14—H14A	109.0	O3—Cl1—O1	107.8 (2)
C15—C14—H14A	109.0	O4—Cl1—O1	111.0 (2)
N1—Mn1—N3—C21	80.4 (3)	C4—N2—C3—C2	−176.4 (3)
N1i—Mn1—N3—C21	−99.6 (3)	C21—N3—C22—C23	−0.7 (5)
N5—Mn1—N3—C21	−11.1 (3)	Mn1—N3—C22—C23	173.3 (3)
N5i—Mn1—N3—C21	168.9 (3)	C11—N6—C14—C15	67.0 (5)
N1—Mn1—N3—C22	−92.2 (3)	C13—N6—C14—C15	−113.2 (5)
N1i—Mn1—N3—C22	87.8 (3)	C20—C15—C14—N6	−138.7 (4)
N5—Mn1—N3—C22	176.3 (3)	C16—C15—C14—N6	44.1 (5)
N5i—Mn1—N3—C22	−3.7 (3)	C11—N5—C12—C13	0.0 (4)
N3i—Mn1—N1—C1	161.6 (3)	Mn1—N5—C12—C13	−169.7 (3)
N3—Mn1—N1—C1	−18.4 (3)	C21—N4—C23—C22	1.0 (5)
N5—Mn1—N1—C1	72.3 (3)	C24—N4—C23—C22	−179.5 (4)
N5i—Mn1—N1—C1	−107.7 (3)	N3—C22—C23—N4	−0.2 (5)
N3i—Mn1—N1—C2	−26.1 (3)	N5—C12—C13—N6	−0.3 (5)
N3—Mn1—N1—C2	153.9 (3)	C11—N6—C13—C12	0.4 (4)
N5—Mn1—N1—C2	−115.4 (3)	C14—N6—C13—C12	−179.4 (4)
N5i—Mn1—N1—C2	64.6 (3)	C21—N4—C24—C25	93.9 (4)
N1—Mn1—N5—C11	−2.1 (3)	C23—N4—C24—C25	−85.5 (5)
N1i—Mn1—N5—C11	177.9 (3)	C30—C25—C24—N4	−117.2 (4)
N3i—Mn1—N5—C11	−91.6 (3)	C26—C25—C24—N4	66.7 (5)
N3—Mn1—N5—C11	88.4 (3)	C16—C15—C20—C19	0.2 (8)
N1—Mn1—N5—C12	165.2 (3)	C14—C15—C20—C19	−177.2 (5)
N1i—Mn1—N5—C12	−14.8 (3)	C30—C25—C26—C27	2.0 (7)
N3i—Mn1—N5—C12	75.7 (3)	C24—C25—C26—C27	178.2 (4)
N3—Mn1—N5—C12	−104.3 (3)	C28—C27—C26—C25	−1.4 (8)
C12—N5—C11—N6	0.3 (4)	C6—C5—C10—C9	−0.7 (7)
Mn1—N5—C11—N6	169.7 (2)	C4—C5—C10—C9	177.2 (5)
C13—N6—C11—N5	−0.5 (4)	C10—C5—C6—C7	1.5 (7)
C14—N6—C11—N5	179.3 (3)	C4—C5—C6—C7	−176.3 (5)
C2—N1—C1—N2	0.2 (4)	C16—C17—C18—C19	−0.9 (8)
Mn1—N1—C1—N2	173.80 (19)	C30—C29—C28—C27	2.1 (10)
C3—N2—C1—N1	−0.5 (4)	C26—C27—C28—C29	−0.7 (9)
C4—N2—C1—N1	176.5 (3)	C5—C10—C9—C8	−1.0 (9)
C22—N3—C21—N4	1.4 (4)	C5—C6—C7—C8	−0.7 (10)
Mn1—N3—C21—N4	−172.5 (2)	C20—C15—C16—C17	−0.4 (6)
C23—N4—C21—N3	−1.6 (4)	C14—C15—C16—C17	176.9 (4)
C24—N4—C21—N3	178.9 (3)	C18—C17—C16—C15	0.8 (7)
C1—N2—C4—C5	−105.6 (4)	C26—C25—C30—C29	−0.6 (8)
C3—N2—C4—C5	70.8 (5)	C24—C25—C30—C29	−176.8 (5)
C6—C5—C4—N2	−106.6 (4)	C28—C29—C30—C25	−1.5 (9)
C10—C5—C4—N2	75.7 (5)	C6—C7—C8—C9	−1.0 (11)
C1—N1—C2—C3	0.2 (4)	C10—C9—C8—C7	1.8 (11)
Mn1—N1—C2—C3	−173.7 (2)	C15—C20—C19—C18	−0.3 (10)
N1—C2—C3—N2	−0.5 (4)	C17—C18—C19—C20	0.7 (10)
C1—N2—C3—C2	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.93	2.49	3.286 (4)	144
C14—H14A···O4	0.97	2.53	3.461 (6)	160
C21—H21A···O3	0.93	2.56	3.371 (5)	145
C24—H24B···O1ii	0.97	2.53	3.469 (5)	164

Table 1

Selected bond lengths (Å)

Mn1—N1	2.158 (2)
Mn1—N3	2.158 (2)
Mn1—N5	2.181 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1	0.93	2.49	3.286 (4)	144
C14—H14A⋯O4	0.97	2.53	3.461 (6)	160
C21—H21A⋯O3	0.93	2.56	3.371 (5)	145
C24—H24B⋯O1i	0.97	2.53	3.469 (5)	164

Symmetry code: (i) .