(Formato-κO,O')bis-(1,10-phenanthroline-κN,N')manganese(II) perchlorate.

In the title complex, [Mn(CHO(2))(C(12)H(8)N(2))(2)]ClO(4), the Mn(II) cation is chelated by two 1,10-phenanthroline (phen) ligands and one formate anion in a distorted MnN(4)O(2) octa-hedral geometry. The two phen planes are oriented at a dihedral angle of 57.48 (11)°. The perchlorate anion links with the Mn complex cation via weak C-H⋯O hydrogen bonding.

Related literature

For general background to manganese(II)–phen complexes and related structures, see: Zhu et al. (2008 ▶); Hao et al. (2008 ▶); Zhang (2004 ▶); Xu & Xu (2005 ▶).

Experimental

Crystal data

[Mn(CHO2)(C12H8N2)2]ClO4

M = 559.82

Monoclinic,

a = 13.0752 (10) Å

b = 10.9532 (9) Å

c = 17.4811 (14) Å

β = 111.4950 (10)°

V = 2329.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.73 mm−1

T = 293 K

0.30 × 0.25 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.803, T max = 0.889

22324 measured reflections

5752 independent reflections

4237 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.176

S = 1.07

5752 reflections

334 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049277/xu2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049277/xu2641Isup2.hkl

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

[Mn(CHO2)(C12H8N2)2]ClO4	F(000) = 1140
Mr = 559.82	Dx = 1.596 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5752 reflections
a = 13.0752 (10) Å	θ = 2.2–28.3°
b = 10.9532 (9) Å	µ = 0.73 mm−1
c = 17.4811 (14) Å	T = 293 K
β = 111.495 (1)°	Prism, pink
V = 2329.4 (3) Å3	0.30 × 0.25 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	5752 independent reflections
Radiation source: fine-focus sealed tube	4237 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→12
Tmin = 0.803, Tmax = 0.889	k = −14→14
22324 measured reflections	l = −23→23

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0272P)2 + 7.2414P] where P = (Fo2 + 2Fc2)/3
5752 reflections	(Δ/σ)max = 0.002
334 parameters	Δρmax = 0.88 e Å−3
2 restraints	Δρmin = −0.65 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
Mn1	0.28574 (5)	0.75685 (6)	0.09973 (4)	0.03794 (18)
C12	0.1291 (4)	0.7365 (4)	0.1859 (3)	0.0485 (11)
N3	0.4324 (3)	0.7221 (3)	0.0732 (2)	0.0513 (10)
N4	0.2276 (3)	0.6351 (4)	−0.0041 (2)	0.0529 (10)
C7	0.2343 (4)	0.6349 (4)	0.3166 (3)	0.0496 (11)
C23	0.3015 (4)	0.6173 (4)	−0.0406 (3)	0.0493 (11)
C11	0.2290 (4)	0.6786 (4)	0.2398 (3)	0.0442 (10)
N2	0.3142 (3)	0.6696 (4)	0.2139 (2)	0.0507 (10)
N1	0.1283 (3)	0.7782 (4)	0.1127 (2)	0.0530 (10)
C24	0.4105 (4)	0.6658 (4)	−0.0005 (3)	0.0486 (11)
C6	0.1396 (5)	0.6481 (5)	0.3396 (3)	0.0595 (13)
H6	0.1420	0.6168	0.3897	0.071*
C16	0.4886 (5)	0.6533 (5)	−0.0370 (3)	0.0582 (13)
C10	0.4052 (4)	0.6172 (5)	0.2638 (3)	0.0610 (14)
H10	0.4641	0.6098	0.2463	0.073*
C8	0.3318 (5)	0.5804 (5)	0.3676 (3)	0.0632 (14)
H8	0.3383	0.5501	0.4189	0.076*
C4	0.0416 (4)	0.7523 (5)	0.2128 (3)	0.0540 (12)
C3	−0.0515 (4)	0.8147 (6)	0.1588 (4)	0.0683 (15)
H3	−0.1117	0.8282	0.1739	0.082*
C2	−0.0533 (5)	0.8549 (6)	0.0853 (4)	0.0741 (17)
H2	−0.1145	0.8957	0.0495	0.089*
C5	0.0484 (5)	0.7044 (5)	0.2905 (3)	0.0617 (14)
H5	−0.0112	0.7124	0.3071	0.074*
C19	0.2753 (5)	0.5548 (5)	−0.1155 (3)	0.0603 (14)
C15	0.5929 (5)	0.7011 (5)	0.0048 (4)	0.0753 (18)
H15	0.6467	0.6964	−0.0182	0.090*
C13	0.5328 (5)	0.7650 (5)	0.1118 (4)	0.0645 (14)
H13	0.5487	0.8034	0.1623	0.077*
C22	0.1285 (5)	0.5872 (5)	−0.0392 (4)	0.0679 (15)
H22	0.0778	0.5983	−0.0139	0.082*
C9	0.4173 (5)	0.5725 (5)	0.3409 (3)	0.0673 (15)
H9	0.4833	0.5374	0.3742	0.081*
C17	0.4584 (6)	0.5935 (5)	−0.1153 (4)	0.0717 (17)
H17	0.5093	0.5873	−0.1409	0.086*
C1	0.0378 (5)	0.8345 (6)	0.0640 (3)	0.0686 (16)
H1	0.0353	0.8616	0.0130	0.082*
C20	0.1692 (6)	0.5062 (5)	−0.1501 (4)	0.0750 (18)
H20	0.1485	0.4633	−0.1994	0.090*
C18	0.3560 (6)	0.5459 (5)	−0.1523 (3)	0.0735 (18)
H18	0.3381	0.5067	−0.2028	0.088*
C14	0.6158 (5)	0.7550 (6)	0.0797 (4)	0.0763 (17)
H14	0.6860	0.7846	0.1090	0.092*
C21	0.0962 (6)	0.5213 (6)	−0.1121 (4)	0.0781 (18)
H21	0.0260	0.4881	−0.1344	0.094*
Cl1	−0.21638 (13)	0.81668 (17)	0.34147 (10)	0.0761 (5)
O2	0.3515 (3)	0.9326 (3)	0.1610 (2)	0.0695 (10)
O1	0.2508 (3)	0.9390 (4)	0.0303 (2)	0.0709 (11)
C25	0.3023 (5)	0.9903 (5)	0.0963 (3)	0.0607 (13)
H25A	0.3047	1.0752	0.0977	0.073*
O6	−0.3243 (5)	0.8154 (9)	0.3342 (5)	0.193 (4)
O3	−0.1958 (7)	0.8782 (9)	0.2849 (6)	0.243 (6)
O4	−0.1710 (10)	0.7089 (8)	0.3465 (11)	0.341 (10)
O5	−0.1664 (12)	0.856 (2)	0.4119 (7)	0.436 (12)

	U11	U22	U33	U12	U13	U23
Mn1	0.0414 (4)	0.0420 (3)	0.0373 (3)	0.0022 (3)	0.0225 (3)	−0.0034 (3)
C12	0.048 (3)	0.048 (3)	0.049 (2)	−0.006 (2)	0.018 (2)	−0.008 (2)
N3	0.054 (3)	0.044 (2)	0.059 (2)	0.0012 (18)	0.023 (2)	−0.0032 (18)
N4	0.055 (3)	0.053 (2)	0.053 (2)	−0.003 (2)	0.022 (2)	−0.0008 (19)
C7	0.058 (3)	0.042 (2)	0.048 (2)	−0.002 (2)	0.020 (2)	−0.002 (2)
C23	0.066 (3)	0.039 (2)	0.048 (2)	0.005 (2)	0.027 (2)	0.0051 (19)
C11	0.050 (3)	0.040 (2)	0.044 (2)	−0.004 (2)	0.019 (2)	−0.0073 (18)
N2	0.046 (2)	0.052 (2)	0.055 (2)	0.0070 (19)	0.0199 (19)	−0.0019 (19)
N1	0.051 (2)	0.060 (3)	0.047 (2)	0.0073 (19)	0.0167 (19)	0.0043 (18)
C24	0.064 (3)	0.039 (2)	0.051 (3)	0.008 (2)	0.030 (2)	0.006 (2)
C6	0.070 (4)	0.061 (3)	0.053 (3)	−0.009 (3)	0.029 (3)	−0.001 (2)
C16	0.071 (4)	0.046 (3)	0.072 (3)	0.011 (3)	0.043 (3)	0.012 (2)
C10	0.051 (3)	0.059 (3)	0.072 (3)	0.012 (3)	0.022 (3)	−0.004 (3)
C8	0.075 (4)	0.055 (3)	0.054 (3)	0.007 (3)	0.017 (3)	0.005 (2)
C4	0.045 (3)	0.059 (3)	0.060 (3)	−0.003 (2)	0.021 (2)	−0.010 (2)
C3	0.045 (3)	0.084 (4)	0.074 (4)	0.003 (3)	0.019 (3)	−0.013 (3)
C2	0.051 (3)	0.092 (5)	0.068 (4)	0.022 (3)	0.010 (3)	0.001 (3)
C5	0.057 (3)	0.073 (4)	0.065 (3)	−0.009 (3)	0.034 (3)	−0.009 (3)
C19	0.086 (4)	0.046 (3)	0.049 (3)	0.010 (3)	0.024 (3)	0.001 (2)
C15	0.074 (4)	0.060 (3)	0.113 (5)	0.011 (3)	0.060 (4)	0.015 (4)
C13	0.056 (3)	0.057 (3)	0.078 (4)	−0.004 (3)	0.023 (3)	−0.007 (3)
C22	0.062 (4)	0.064 (3)	0.076 (4)	−0.010 (3)	0.023 (3)	−0.009 (3)
C9	0.061 (4)	0.066 (3)	0.063 (3)	0.019 (3)	0.009 (3)	0.009 (3)
C17	0.102 (5)	0.063 (3)	0.072 (4)	0.016 (3)	0.058 (4)	0.010 (3)
C1	0.065 (4)	0.083 (4)	0.054 (3)	0.019 (3)	0.017 (3)	0.011 (3)
C20	0.098 (5)	0.054 (3)	0.058 (3)	−0.005 (3)	0.012 (3)	−0.013 (3)
C18	0.120 (6)	0.057 (3)	0.054 (3)	0.021 (4)	0.045 (4)	0.006 (3)
C14	0.054 (3)	0.069 (4)	0.109 (5)	−0.002 (3)	0.035 (3)	0.001 (4)
C21	0.079 (5)	0.067 (4)	0.078 (4)	−0.014 (3)	0.017 (4)	−0.014 (3)
Cl1	0.0668 (10)	0.0934 (11)	0.0773 (10)	0.0128 (9)	0.0371 (8)	0.0185 (9)
O2	0.080 (3)	0.062 (2)	0.062 (2)	−0.0046 (19)	0.021 (2)	−0.0075 (17)
O1	0.088 (3)	0.066 (2)	0.058 (2)	0.009 (2)	0.026 (2)	0.0048 (17)
C25	0.067 (4)	0.062 (3)	0.056 (3)	0.005 (3)	0.026 (3)	−0.001 (3)
O6	0.095 (5)	0.290 (10)	0.239 (8)	0.044 (6)	0.111 (6)	0.058 (8)
O3	0.218 (9)	0.309 (11)	0.290 (10)	0.137 (8)	0.198 (9)	0.221 (9)
O4	0.315 (13)	0.132 (7)	0.77 (3)	0.072 (8)	0.431 (18)	0.115 (12)
O5	0.305 (17)	0.73 (4)	0.158 (9)	0.032 (19)	−0.046 (10)	−0.180 (15)

Mn1—N1	2.165 (4)	C4—C5	1.428 (7)
Mn1—N2	2.119 (4)	C3—C2	1.349 (8)
Mn1—N3	2.165 (4)	C3—H3	0.9300
Mn1—N4	2.154 (4)	C2—C1	1.390 (8)
Mn1—O1	2.292 (4)	C2—H2	0.9300
Mn1—O2	2.218 (4)	C5—H5	0.9300
C12—N1	1.354 (6)	C19—C20	1.400 (8)
C12—C4	1.398 (6)	C19—C18	1.426 (8)
C12—C11	1.447 (6)	C15—C14	1.366 (9)
N3—C13	1.323 (7)	C15—H15	0.9300
N3—C24	1.362 (6)	C13—C14	1.397 (8)
N4—C22	1.323 (7)	C13—H13	0.9300
N4—C23	1.354 (6)	C22—C21	1.388 (8)
C7—C11	1.402 (6)	C22—H22	0.9300
C7—C8	1.394 (7)	C9—H9	0.9300
C7—C6	1.443 (7)	C17—C18	1.360 (9)
C23—C19	1.404 (6)	C17—H17	0.9300
C23—C24	1.439 (7)	C1—H1	0.9300
C11—N2	1.352 (6)	C20—C21	1.358 (9)
N2—C10	1.321 (6)	C20—H20	0.9300
N1—C1	1.329 (6)	C18—H18	0.9300
C24—C16	1.396 (7)	C14—H14	0.9300
C6—C5	1.338 (7)	C21—H21	0.9300
C6—H6	0.9300	Cl1—O5	1.240 (10)
C16—C15	1.392 (8)	Cl1—O3	1.304 (6)
C16—C17	1.436 (8)	Cl1—O4	1.310 (8)
C10—C9	1.387 (7)	Cl1—O6	1.369 (6)
C10—H10	0.9300	O2—C25	1.249 (6)
C8—C9	1.363 (8)	O1—C25	1.237 (6)
C8—H8	0.9300	C25—H25A	0.9300
C4—C3	1.414 (7)
N2—Mn1—N4	113.60 (16)	C12—C4—C5	120.1 (5)
N2—Mn1—N1	78.20 (15)	C3—C4—C5	123.4 (5)
N4—Mn1—N1	95.73 (16)	C2—C3—C4	120.2 (5)
N2—Mn1—N3	105.00 (15)	C2—C3—H3	119.9
N4—Mn1—N3	77.15 (15)	C4—C3—H3	119.9
N1—Mn1—N3	172.86 (15)	C3—C2—C1	119.0 (5)
N2—Mn1—O2	91.90 (15)	C3—C2—H2	120.5
N4—Mn1—O2	154.06 (15)	C1—C2—H2	120.5
N1—Mn1—O2	94.05 (16)	C6—C5—C4	120.7 (5)
N3—Mn1—O2	92.23 (15)	C6—C5—H5	119.7
N2—Mn1—O1	145.38 (14)	C4—C5—H5	119.7
N4—Mn1—O1	98.79 (15)	C23—C19—C20	117.0 (5)
N1—Mn1—O1	87.04 (15)	C23—C19—C18	119.1 (6)
N3—Mn1—O1	93.45 (15)	C20—C19—C18	124.0 (5)
O2—Mn1—O1	57.78 (14)	C16—C15—C14	119.6 (6)
N1—C12—C4	123.5 (5)	C16—C15—H15	120.2
N1—C12—C11	117.1 (4)	C14—C15—H15	120.2
C4—C12—C11	119.3 (4)	N3—C13—C14	122.6 (6)
C13—N3—C24	118.0 (5)	N3—C13—H13	118.7
C13—N3—Mn1	128.3 (4)	C14—C13—H13	118.7
C24—N3—Mn1	112.8 (3)	N4—C22—C21	123.3 (6)
C22—N4—C23	118.1 (5)	N4—C22—H22	118.3
C22—N4—Mn1	128.3 (4)	C21—C22—H22	118.3
C23—N4—Mn1	113.2 (3)	C8—C9—C10	119.7 (5)
C11—C7—C8	118.2 (5)	C8—C9—H9	120.2
C11—C7—C6	119.1 (5)	C10—C9—H9	120.2
C8—C7—C6	122.7 (5)	C18—C17—C16	120.5 (5)
N4—C23—C19	122.5 (5)	C18—C17—H17	119.7
N4—C23—C24	117.9 (4)	C16—C17—H17	119.7
C19—C23—C24	119.6 (5)	N1—C1—C2	123.5 (5)
N2—C11—C7	122.6 (4)	N1—C1—H1	118.2
N2—C11—C12	118.1 (4)	C2—C1—H1	118.2
C7—C11—C12	119.3 (4)	C21—C20—C19	120.3 (5)
C10—N2—C11	117.6 (4)	C21—C20—H20	119.8
C10—N2—Mn1	128.5 (4)	C19—C20—H20	119.8
C11—N2—Mn1	113.7 (3)	C17—C18—C19	121.4 (5)
C1—N1—C12	117.3 (5)	C17—C18—H18	119.3
C1—N1—Mn1	129.8 (4)	C19—C18—H18	119.3
C12—N1—Mn1	112.6 (3)	C15—C14—C13	119.3 (6)
N3—C24—C16	122.8 (5)	C15—C14—H14	120.3
N3—C24—C23	117.1 (4)	C13—C14—H14	120.3
C16—C24—C23	120.1 (5)	C20—C21—C22	118.8 (6)
C5—C6—C7	121.4 (5)	C20—C21—H21	120.6
C5—C6—H6	119.3	C22—C21—H21	120.6
C7—C6—H6	119.3	O5—Cl1—O3	113.1 (12)
C15—C16—C24	117.6 (5)	O5—Cl1—O4	100.6 (11)
C15—C16—C17	123.1 (5)	O3—Cl1—O4	107.7 (6)
C24—C16—C17	119.2 (6)	O5—Cl1—O6	104.3 (8)
N2—C10—C9	123.3 (5)	O3—Cl1—O6	115.3 (5)
N2—C10—H10	118.3	O4—Cl1—O6	115.0 (6)
C9—C10—H10	118.3	C25—O2—Mn1	91.2 (3)
C9—C8—C7	118.7 (5)	C25—O1—Mn1	88.2 (3)
C9—C8—H8	120.7	O1—C25—O2	122.6 (5)
C7—C8—H8	120.7	O1—C25—H25A	118.7
C12—C4—C3	116.5 (5)	O2—C25—H25A	118.7
N2—Mn1—N3—C13	−68.4 (5)	Mn1—N3—C24—C23	−11.8 (5)
N4—Mn1—N3—C13	−179.7 (5)	N4—C23—C24—N3	2.5 (6)
N1—Mn1—N3—C13	175.8 (11)	C19—C23—C24—N3	−178.0 (4)
O2—Mn1—N3—C13	24.2 (5)	N4—C23—C24—C16	−177.9 (4)
O1—Mn1—N3—C13	82.1 (5)	C19—C23—C24—C16	1.6 (7)
N2—Mn1—N3—C24	123.4 (3)	C11—C7—C6—C5	−2.1 (7)
N4—Mn1—N3—C24	12.1 (3)	C8—C7—C6—C5	177.8 (5)
N1—Mn1—N3—C24	7.6 (14)	N3—C24—C16—C15	0.0 (7)
O2—Mn1—N3—C24	−144.0 (3)	C23—C24—C16—C15	−179.5 (4)
O1—Mn1—N3—C24	−86.1 (3)	N3—C24—C16—C17	−179.5 (4)
N2—Mn1—N4—C22	75.1 (5)	C23—C24—C16—C17	1.0 (7)
N1—Mn1—N4—C22	−4.5 (5)	C11—N2—C10—C9	−0.6 (8)
N3—Mn1—N4—C22	176.0 (5)	Mn1—N2—C10—C9	173.9 (4)
O2—Mn1—N4—C22	−116.2 (5)	C11—C7—C8—C9	0.2 (7)
O1—Mn1—N4—C22	−92.4 (5)	C6—C7—C8—C9	−179.7 (5)
N2—Mn1—N4—C23	−111.8 (3)	N1—C12—C4—C3	0.4 (7)
N1—Mn1—N4—C23	168.6 (3)	C11—C12—C4—C3	177.0 (4)
N3—Mn1—N4—C23	−10.8 (3)	N1—C12—C4—C5	179.3 (5)
O2—Mn1—N4—C23	57.0 (5)	C11—C12—C4—C5	−4.1 (7)
O1—Mn1—N4—C23	80.7 (3)	C12—C4—C3—C2	0.5 (8)
C22—N4—C23—C19	2.7 (7)	C5—C4—C3—C2	−178.3 (6)
Mn1—N4—C23—C19	−171.2 (4)	C4—C3—C2—C1	−0.3 (9)
C22—N4—C23—C24	−177.8 (4)	C7—C6—C5—C4	0.7 (8)
Mn1—N4—C23—C24	8.3 (5)	C12—C4—C5—C6	2.5 (8)
C8—C7—C11—N2	0.1 (7)	C3—C4—C5—C6	−178.7 (5)
C6—C7—C11—N2	−180.0 (4)	N4—C23—C19—C20	−2.6 (7)
C8—C7—C11—C12	−179.5 (4)	C24—C23—C19—C20	177.9 (5)
C6—C7—C11—C12	0.4 (7)	N4—C23—C19—C18	176.5 (4)
N1—C12—C11—N2	−0.2 (6)	C24—C23—C19—C18	−3.0 (7)
C4—C12—C11—N2	−177.0 (4)	C24—C16—C15—C14	1.6 (8)
N1—C12—C11—C7	179.4 (4)	C17—C16—C15—C14	−178.9 (5)
C4—C12—C11—C7	2.7 (7)	C24—N3—C13—C14	0.2 (8)
C7—C11—N2—C10	0.1 (7)	Mn1—N3—C13—C14	−167.4 (4)
C12—C11—N2—C10	179.7 (4)	C23—N4—C22—C21	−0.9 (8)
C7—C11—N2—Mn1	−175.2 (3)	Mn1—N4—C22—C21	172.0 (4)
C12—C11—N2—Mn1	4.4 (5)	C7—C8—C9—C10	−0.7 (8)
N4—Mn1—N2—C10	89.4 (5)	N2—C10—C9—C8	0.9 (9)
N1—Mn1—N2—C10	−179.5 (5)	C15—C16—C17—C18	178.4 (5)
N3—Mn1—N2—C10	7.1 (5)	C24—C16—C17—C18	−2.1 (8)
O2—Mn1—N2—C10	−85.8 (4)	C12—N1—C1—C2	1.7 (9)
O1—Mn1—N2—C10	−112.8 (5)	Mn1—N1—C1—C2	−171.3 (5)
N4—Mn1—N2—C11	−96.0 (3)	C3—C2—C1—N1	−0.9 (10)
N1—Mn1—N2—C11	−4.8 (3)	C23—C19—C20—C21	0.7 (8)
N3—Mn1—N2—C11	−178.3 (3)	C18—C19—C20—C21	−178.3 (6)
O2—Mn1—N2—C11	88.9 (3)	C16—C17—C18—C19	0.7 (9)
O1—Mn1—N2—C11	61.9 (4)	C23—C19—C18—C17	1.9 (8)
C4—C12—N1—C1	−1.5 (7)	C20—C19—C18—C17	−179.0 (6)
C11—C12—N1—C1	−178.2 (5)	C16—C15—C14—C13	−2.2 (9)
C4—C12—N1—Mn1	172.7 (4)	N3—C13—C14—C15	1.4 (9)
C11—C12—N1—Mn1	−4.0 (5)	C19—C20—C21—C22	0.9 (9)
N2—Mn1—N1—C1	178.0 (5)	N4—C22—C21—C20	−0.9 (10)
N4—Mn1—N1—C1	−69.1 (5)	N2—Mn1—O2—C25	−159.4 (3)
N3—Mn1—N1—C1	−64.7 (14)	N4—Mn1—O2—C25	30.9 (5)
O2—Mn1—N1—C1	86.9 (5)	N1—Mn1—O2—C25	−81.1 (3)
O1—Mn1—N1—C1	29.5 (5)	N3—Mn1—O2—C25	95.5 (3)
N2—Mn1—N1—C12	4.7 (3)	O1—Mn1—O2—C25	2.8 (3)
N4—Mn1—N1—C12	117.7 (3)	N2—Mn1—O1—C25	29.6 (5)
N3—Mn1—N1—C12	122.1 (12)	N4—Mn1—O1—C25	−170.8 (3)
O2—Mn1—N1—C12	−86.4 (3)	N1—Mn1—O1—C25	93.8 (3)
O1—Mn1—N1—C12	−143.8 (3)	N3—Mn1—O1—C25	−93.3 (3)
C13—N3—C24—C16	−0.9 (7)	O2—Mn1—O1—C25	−2.9 (3)
Mn1—N3—C24—C16	168.6 (4)	Mn1—O1—C25—O2	5.1 (6)
C13—N3—C24—C23	178.6 (4)	Mn1—O2—C25—O1	−5.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.57	3.468 (7)	164
C5—H5···O4	0.93	2.43	3.355 (9)	174
C6—H6···O1ii	0.93	2.42	3.254 (7)	149
C18—H18···O2iii	0.93	2.54	3.250 (6)	134

Table 1

Selected bond lengths (Å)

Mn1—N1	2.165 (4)
Mn1—N2	2.119 (4)
Mn1—N3	2.165 (4)
Mn1—N4	2.154 (4)
Mn1—O1	2.292 (4)
Mn1—O2	2.218 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.57	3.468 (7)	164
C5—H5⋯O4	0.93	2.43	3.355 (9)	174
C6—H6⋯O1ii	0.93	2.42	3.254 (7)	149
C18—H18⋯O2iii	0.93	2.54	3.250 (6)	134

Symmetry codes: (i) ; (ii) ; (iii) .