catena-Poly[[manganese(III)-bis-{μ-2-[(2-hy-droxy-eth-yl)imino-meth-yl]-6-meth-oxy-phenolato-κ(3) O (1),N:O (2);κ(3) O (2):N,O (1)}] iodide].

In the title one-dimensional coordination polymer, {[Mn(C10H12NO3)2]I} n , the potentially tetra-dentate (O,O,O,N) 2-[(2-hy-droxy-eth-yl)imino-meth-yl]-6-meth-oxy-phenol (H2 L) ligands are mono-deprotonated (as HL (-)) and coordinated by the metal ions in a tridentate chelate-bridging fashion [2.0111112]. The Mn(III) atom possesses a distorted trans-MnO4N2 octa-hedral coordination environment. The bridging ligands lead to [010]-chain polymeric cations {[Mn(HL)2](+)} n in the crystal. The charge-balancing iodide ions are disordered over two sites in a 0.690 (2):0.310 (2) ratio and a weak O-H⋯I hydrogen bond occurs. The crystal studied was found to be a racemic twin.

Related literature

For the related structure of {[Mn(C9H10NO2)2]Cl}, see: Zhang et al. (2005 ▶). For further synthetic details, see: Babich et al. (1996 ▶); Vinogradova et al. (2002 ▶); Makhankova et al. (2002 ▶); Nesterov et al. (2012 ▶); Chygorin et al. (2012 ▶). For bond-valence sum calculations, see: Brown & Altermatt (1985 ▶). For coordination mode notation, see: Coxall et al. (2000 ▶).

Experimental

Crystal data

[Mn(C10H12NO3)2]I

M = 570.25

Orthorhombic,

a = 18.880 (2) Å

b = 5.8979 (10) Å

c = 20.916 (2) Å

V = 2329.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.93 mm−1

T = 298 K

0.40 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.513, T max = 0.699

7841 measured reflections

4752 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.173

S = 0.92

4752 reflections

282 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.49 e Å−3

Δρmin = −0.66 e Å−3

Absolute structure: Flack (1983 ▶), 1276 Friedel pairs

Flack parameter: 0.59 (3)

Data collection: CrysAlis CCD (Agilent, 2011 ▶); cell refinement: CrysAlis RED (Agilent, 2011 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012695/hb7060sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012695/hb7060Isup2.hkl

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

[Mn(C10H12NO3)2]I	F(000) = 1136
Mr = 570.25	Dx = 1.626 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 861 reflections
a = 18.880 (2) Å	θ = 2.9–32.3°
b = 5.8979 (10) Å	µ = 1.93 mm−1
c = 20.916 (2) Å	T = 298 K
V = 2329.1 (5) Å3	Block, brown
Z = 4	0.40 × 0.20 × 0.20 mm

Agilent Xcalibur Sapphire3 diffractometer	4752 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2094 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 16.1827 pixels mm-1	θmax = 30.0°, θmin = 3.5°
ω scans	h = −26→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→8
Tmin = 0.513, Tmax = 0.699	l = −29→28
7841 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)] = 0.076	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
4752 reflections	Δρmax = 1.49 e Å−3
282 parameters	Δρmin = −0.66 e Å−3
1 restraint	Absolute structure: Flack (1983), 1276 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.59 (3)

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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)
I1A	0.08961 (6)	0.43638 (19)	0.26350 (5)	0.0583 (4)	0.690 (2)
I1B	0.08839 (17)	−0.0686 (6)	0.20195 (17)	0.0752 (12)	0.310 (2)
Mn1	−0.00346 (8)	−0.2483 (4)	−0.01586 (13)	0.0360 (3)
O1	0.0867 (4)	−0.3014 (13)	−0.0471 (4)	0.046 (2)
N1	−0.0240 (4)	−0.0371 (15)	−0.0905 (5)	0.036 (2)
C1	0.0895 (7)	−0.0934 (19)	−0.1467 (5)	0.045 (3)
N2	0.0178 (4)	−0.4584 (16)	0.0605 (4)	0.036 (2)
O2	0.2049 (4)	−0.5108 (13)	−0.0732 (4)	0.057 (2)
C2	0.1194 (6)	−0.2539 (19)	−0.1020 (6)	0.041 (3)
O3	−0.0923 (4)	−0.1935 (15)	0.0153 (4)	0.049 (2)
C3	0.1822 (6)	−0.354 (3)	−0.1174 (7)	0.058 (4)
O4	−0.2124 (5)	0.0167 (19)	0.0405 (6)	0.095 (4)
C4	0.2190 (7)	−0.297 (2)	−0.1702 (6)	0.060 (4)
H4	0.2633	−0.3603	−0.1782	0.072*
O5	−0.0455 (4)	0.4550 (13)	−0.0775 (4)	0.048 (2)
H5	−0.0337	0.4208	−0.1158	0.072*
C5	0.1889 (7)	−0.138 (2)	−0.2134 (6)	0.067 (4)
H5A	0.2124	−0.1046	−0.2514	0.081*
O6	0.0391 (4)	−0.9640 (12)	0.0445 (4)	0.047 (2)
H6	0.0484	−0.9805	0.0846	0.071*
C6	0.1268 (7)	−0.035 (2)	−0.2004 (6)	0.053 (3)
H6A	0.1093	0.0758	−0.2279	0.063*
C7	0.0196 (6)	0.000 (2)	−0.1382 (6)	0.042 (3)
H7	0.0037	0.0981	−0.1700	0.050*
C8	0.2479 (9)	−0.695 (2)	−0.0966 (9)	0.078 (5)
H8A	0.2609	−0.7920	−0.0616	0.117*
H8B	0.2900	−0.6354	−0.1162	0.117*
H8C	0.2216	−0.7807	−0.1275	0.117*
C9	−0.0945 (6)	−0.3948 (19)	0.1152 (5)	0.040 (3)
C10	−0.1217 (6)	−0.256 (2)	0.0695 (6)	0.039 (3)
C11	−0.1901 (6)	−0.1460 (19)	0.0850 (6)	0.041 (3)
C12	−0.2257 (6)	−0.200 (2)	0.1367 (7)	0.056 (4)
H12	−0.2695	−0.1327	0.1443	0.067*
C13	−0.1983 (6)	−0.358 (2)	0.1810 (8)	0.065 (4)
H13	−0.2246	−0.4019	0.2165	0.078*
C14	−0.1321 (7)	−0.445 (2)	0.1705 (6)	0.060 (4)
H14	−0.1119	−0.5401	0.2010	0.072*
C15	−0.0250 (6)	−0.496 (2)	0.1054 (6)	0.048 (3)
H15	−0.0105	−0.6015	0.1359	0.058*
C16	−0.2537 (8)	0.190 (2)	0.0618 (7)	0.065 (4)
H16A	−0.2654	0.2880	0.0267	0.098*
H16B	−0.2285	0.2746	0.0937	0.098*
H16C	−0.2964	0.1298	0.0800	0.098*
C17	−0.0928 (5)	0.0769 (15)	−0.0985 (7)	0.049 (3)
H17A	−0.1310	−0.0249	−0.0869	0.059*
H17B	−0.0993	0.1225	−0.1427	0.059*
C18	−0.0929 (6)	0.2899 (19)	−0.0539 (6)	0.044 (3)
H18A	−0.1403	0.3529	−0.0517	0.053*
H18B	−0.0789	0.2458	−0.0110	0.053*
C19	0.0885 (6)	−0.7926 (19)	0.0222 (7)	0.048 (4)
H19A	0.0769	−0.7521	−0.0215	0.058*
H19B	0.1360	−0.8551	0.0224	0.058*
C20	0.0869 (5)	−0.5841 (19)	0.0628 (5)	0.040 (3)
H20A	0.1244	−0.4829	0.0491	0.048*
H20B	0.0966	−0.6267	0.1068	0.048*

	U11	U22	U33	U12	U13	U23
I1A	0.0828 (7)	0.0563 (6)	0.0359 (5)	−0.0091 (7)	−0.0043 (9)	−0.0054 (10)
I1B	0.087 (2)	0.0596 (19)	0.079 (2)	−0.0057 (18)	0.011 (2)	−0.002 (2)
Mn1	0.0441 (6)	0.0298 (5)	0.0340 (6)	0.0027 (6)	0.0010 (7)	0.0055 (6)
O1	0.054 (5)	0.049 (5)	0.036 (4)	0.008 (4)	−0.007 (5)	0.010 (4)
N1	0.039 (5)	0.027 (5)	0.042 (5)	−0.009 (4)	0.005 (5)	−0.015 (5)
C1	0.070 (8)	0.034 (6)	0.031 (5)	0.014 (6)	0.010 (7)	0.000 (5)
N2	0.038 (5)	0.038 (5)	0.033 (5)	0.017 (4)	0.003 (4)	0.014 (5)
O2	0.079 (5)	0.051 (5)	0.040 (5)	0.039 (4)	0.013 (5)	0.008 (5)
C2	0.044 (6)	0.038 (7)	0.043 (7)	−0.003 (5)	0.005 (6)	−0.007 (6)
O3	0.056 (5)	0.054 (6)	0.038 (5)	0.011 (4)	0.014 (5)	0.015 (5)
C3	0.044 (7)	0.087 (10)	0.044 (7)	−0.012 (7)	0.023 (6)	−0.027 (8)
O4	0.075 (6)	0.146 (11)	0.065 (7)	0.057 (7)	−0.009 (6)	−0.006 (8)
C4	0.069 (8)	0.077 (11)	0.034 (7)	0.018 (8)	0.011 (7)	−0.013 (8)
O5	0.069 (5)	0.043 (5)	0.033 (4)	−0.011 (4)	−0.010 (4)	−0.008 (5)
C5	0.097 (10)	0.076 (10)	0.028 (6)	−0.005 (9)	0.020 (7)	−0.011 (7)
O6	0.069 (5)	0.030 (4)	0.043 (4)	−0.010 (4)	−0.009 (5)	0.006 (5)
C6	0.076 (8)	0.048 (7)	0.035 (6)	0.004 (7)	0.008 (7)	0.003 (7)
C7	0.054 (7)	0.028 (7)	0.044 (7)	0.002 (5)	−0.008 (6)	−0.001 (6)
C8	0.085 (8)	0.043 (8)	0.106 (15)	0.012 (7)	0.006 (11)	−0.004 (10)
C9	0.045 (6)	0.041 (7)	0.035 (5)	−0.008 (5)	−0.003 (6)	0.010 (6)
C10	0.051 (7)	0.042 (7)	0.025 (5)	0.002 (5)	−0.003 (6)	−0.004 (6)
C11	0.040 (6)	0.041 (7)	0.041 (6)	0.011 (5)	−0.014 (6)	0.013 (6)
C12	0.048 (7)	0.061 (10)	0.057 (9)	0.006 (7)	−0.009 (7)	0.002 (9)
C13	0.058 (7)	0.065 (9)	0.071 (10)	0.002 (7)	0.036 (8)	0.018 (8)
C14	0.078 (8)	0.062 (9)	0.040 (7)	0.020 (7)	0.007 (7)	0.004 (8)
C15	0.063 (8)	0.042 (8)	0.039 (6)	0.000 (6)	−0.022 (7)	0.007 (6)
C16	0.067 (8)	0.069 (10)	0.059 (9)	0.016 (7)	0.010 (8)	−0.016 (9)
C17	0.029 (5)	0.016 (5)	0.102 (10)	−0.005 (4)	−0.018 (7)	0.016 (7)
C18	0.046 (6)	0.049 (8)	0.037 (6)	−0.010 (6)	−0.010 (6)	0.011 (6)
C19	0.048 (7)	0.025 (7)	0.072 (10)	0.008 (5)	0.006 (7)	−0.010 (7)
C20	0.042 (5)	0.048 (7)	0.030 (5)	−0.010 (5)	−0.018 (6)	0.005 (6)

Mn1—O3	1.829 (8)	O6—H6	0.8625
Mn1—O1	1.849 (8)	C6—H6A	0.9300
Mn1—N1	2.035 (10)	C7—H7	0.9300
Mn1—N2	2.061 (9)	C8—H8A	0.9600
Mn1—O6i	2.247 (8)	C8—H8B	0.9600
Mn1—O5ii	2.315 (8)	C8—H8C	0.9600
O1—C2	1.335 (14)	C9—C10	1.358 (15)
N1—C7	1.312 (14)	C9—C14	1.391 (16)
N1—C17	1.473 (13)	C9—C15	1.457 (17)
C1—C6	1.371 (16)	C10—C11	1.482 (16)
C1—C7	1.443 (16)	C11—C12	1.312 (17)
C1—C2	1.445 (16)	C12—C13	1.414 (19)
N2—C15	1.259 (15)	C12—H12	0.9300
N2—C20	1.502 (13)	C13—C14	1.369 (16)
O2—C3	1.376 (17)	C13—H13	0.9300
O2—C8	1.442 (14)	C14—H14	0.9300
C2—C3	1.363 (16)	C15—H15	0.9300
O3—C10	1.315 (13)	C16—H16A	0.9600
C3—C4	1.349 (18)	C16—H16B	0.9600
O4—C16	1.361 (14)	C16—H16C	0.9600
O4—C11	1.401 (14)	C17—C18	1.566 (16)
C4—C5	1.421 (18)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
O5—C18	1.412 (12)	C18—H18A	0.9700
O5—Mn1i	2.315 (8)	C18—H18B	0.9700
O5—H5	0.8547	C19—C20	1.496 (17)
C5—C6	1.348 (17)	C19—H19A	0.9700
C5—H5A	0.9300	C19—H19B	0.9700
O6—C19	1.453 (13)	C20—H20A	0.9700
O6—Mn1ii	2.247 (8)	C20—H20B	0.9700
O3—Mn1—O1	179.5 (5)	O2—C8—H8C	109.5
O3—Mn1—N1	89.5 (4)	H8A—C8—H8C	109.5
O1—Mn1—N1	90.5 (3)	H8B—C8—H8C	109.5
O3—Mn1—N2	90.5 (4)	C10—C9—C14	121.4 (11)
O1—Mn1—N2	89.6 (3)	C10—C9—C15	119.3 (10)
N1—Mn1—N2	179.2 (5)	C14—C9—C15	119.2 (11)
O3—Mn1—O6i	89.8 (4)	O3—C10—C9	128.1 (11)
O1—Mn1—O6i	89.8 (3)	O3—C10—C11	115.6 (10)
N1—Mn1—O6i	92.4 (3)	C9—C10—C11	116.1 (11)
N2—Mn1—O6i	86.8 (3)	C12—C11—O4	124.0 (10)
O3—Mn1—O5ii	91.0 (4)	C12—C11—C10	121.4 (11)
O1—Mn1—O5ii	89.5 (3)	O4—C11—C10	114.6 (10)
N1—Mn1—O5ii	88.3 (3)	C11—C12—C13	120.8 (11)
N2—Mn1—O5ii	92.5 (4)	C11—C12—H12	119.6
O6i—Mn1—O5ii	179.0 (4)	C13—C12—H12	119.6
C2—O1—Mn1	134.0 (7)	C14—C13—C12	118.6 (12)
C7—N1—C17	113.0 (10)	C14—C13—H13	120.7
C7—N1—Mn1	124.6 (7)	C12—C13—H13	120.7
C17—N1—Mn1	122.3 (8)	C13—C14—C9	121.2 (13)
C6—C1—C7	118.3 (12)	C13—C14—H14	119.4
C6—C1—C2	119.7 (12)	C9—C14—H14	119.4
C7—C1—C2	121.9 (11)	N2—C15—C9	127.5 (11)
C15—N2—C20	116.4 (9)	N2—C15—H15	116.3
C15—N2—Mn1	124.1 (7)	C9—C15—H15	116.3
C20—N2—Mn1	119.4 (7)	O4—C16—H16A	109.5
C3—O2—C8	117.0 (11)	O4—C16—H16B	109.5
O1—C2—C3	121.0 (12)	H16A—C16—H16B	109.5
O1—C2—C1	120.9 (10)	O4—C16—H16C	109.5
C3—C2—C1	118.1 (12)	H16A—C16—H16C	109.5
C10—O3—Mn1	130.1 (8)	H16B—C16—H16C	109.5
C4—C3—C2	122.2 (15)	N1—C17—C18	107.4 (9)
C4—C3—O2	123.9 (11)	N1—C17—H17A	110.2
C2—C3—O2	113.8 (11)	C18—C17—H17A	110.2
C16—O4—C11	118.0 (12)	N1—C17—H17B	110.2
C3—C4—C5	118.7 (13)	C18—C17—H17B	110.2
C3—C4—H4	120.7	H17A—C17—H17B	108.5
C5—C4—H4	120.7	O5—C18—C17	110.1 (9)
C18—O5—Mn1i	122.9 (7)	O5—C18—H18A	109.6
C18—O5—H5	109.4	C17—C18—H18A	109.6
Mn1i—O5—H5	127.6	O5—C18—H18B	109.6
C6—C5—C4	121.1 (12)	C17—C18—H18B	109.6
C6—C5—H5A	119.4	H18A—C18—H18B	108.2
C4—C5—H5A	119.4	O6—C19—C20	112.1 (10)
C19—O6—Mn1ii	124.6 (8)	O6—C19—H19A	109.2
C19—O6—H6	105.1	C20—C19—H19A	109.2
Mn1ii—O6—H6	122.3	O6—C19—H19B	109.2
C5—C6—C1	119.9 (13)	C20—C19—H19B	109.2
C5—C6—H6A	120.0	H19A—C19—H19B	107.9
C1—C6—H6A	120.0	C19—C20—N2	113.9 (9)
N1—C7—C1	127.1 (11)	C19—C20—H20A	108.8
N1—C7—H7	116.5	N2—C20—H20A	108.8
C1—C7—H7	116.5	C19—C20—H20B	108.8
O2—C8—H8A	109.5	N2—C20—H20B	108.8
O2—C8—H8B	109.5	H20A—C20—H20B	107.7
H8A—C8—H8B	109.5
O3—Mn1—O1—C2	−95 (59)	C8—O2—C3—C2	151.0 (12)
N1—Mn1—O1—C2	−10.8 (10)	C2—C3—C4—C5	−4 (2)
N2—Mn1—O1—C2	170.0 (11)	O2—C3—C4—C5	177.9 (11)
O6i—Mn1—O1—C2	−103.2 (10)	C3—C4—C5—C6	4 (2)
O5ii—Mn1—O1—C2	77.5 (10)	C4—C5—C6—C1	−4 (2)
O3—Mn1—N1—C7	−176.6 (9)	C7—C1—C6—C5	−172.8 (12)
O1—Mn1—N1—C7	3.9 (9)	C2—C1—C6—C5	4.3 (19)
N2—Mn1—N1—C7	96 (30)	C17—N1—C7—C1	−177.0 (11)
O6i—Mn1—N1—C7	93.7 (8)	Mn1—N1—C7—C1	−1.4 (16)
O5ii—Mn1—N1—C7	−85.6 (9)	C6—C1—C7—N1	179.4 (12)
O3—Mn1—N1—C17	−1.3 (8)	C2—C1—C7—N1	2.3 (18)
O1—Mn1—N1—C17	179.1 (8)	Mn1—O3—C10—C9	−5.3 (18)
N2—Mn1—N1—C17	−89 (30)	Mn1—O3—C10—C11	168.8 (8)
O6i—Mn1—N1—C17	−91.1 (8)	C14—C9—C10—O3	179.7 (12)
O5ii—Mn1—N1—C17	89.7 (8)	C15—C9—C10—O3	−1.5 (18)
O3—Mn1—N2—C15	−1.5 (10)	C14—C9—C10—C11	5.7 (17)
O1—Mn1—N2—C15	178.0 (10)	C15—C9—C10—C11	−175.6 (11)
N1—Mn1—N2—C15	86 (30)	C16—O4—C11—C12	28.4 (19)
O6i—Mn1—N2—C15	88.2 (10)	C16—O4—C11—C10	−151.5 (12)
O5ii—Mn1—N2—C15	−92.5 (10)	O3—C10—C11—C12	177.8 (11)
O3—Mn1—N2—C20	175.9 (8)	C9—C10—C11—C12	−7.4 (18)
O1—Mn1—N2—C20	−4.6 (8)	O3—C10—C11—O4	−2.3 (15)
N1—Mn1—N2—C20	−97 (30)	C9—C10—C11—O4	172.5 (10)
O6i—Mn1—N2—C20	−94.4 (8)	O4—C11—C12—C13	−177.0 (12)
O5ii—Mn1—N2—C20	84.8 (8)	C10—C11—C12—C13	3 (2)
Mn1—O1—C2—C3	−166.4 (9)	C11—C12—C13—C14	3 (2)
Mn1—O1—C2—C1	14.1 (16)	C12—C13—C14—C9	−5 (2)
C6—C1—C2—O1	175.1 (11)	C10—C9—C14—C13	0 (2)
C7—C1—C2—O1	−7.9 (17)	C15—C9—C14—C13	−178.4 (13)
C6—C1—C2—C3	−4.5 (17)	C20—N2—C15—C9	178.8 (11)
C7—C1—C2—C3	172.5 (12)	Mn1—N2—C15—C9	−3.7 (18)
O1—Mn1—O3—C10	−90 (59)	C10—C9—C15—N2	6.1 (19)
N1—Mn1—O3—C10	−173.4 (10)	C14—C9—C15—N2	−175.1 (13)
N2—Mn1—O3—C10	5.8 (10)	C7—N1—C17—C18	−103.3 (12)
O6i—Mn1—O3—C10	−80.9 (10)	Mn1—N1—C17—C18	81.0 (9)
O5ii—Mn1—O3—C10	98.4 (10)	Mn1i—O5—C18—C17	−162.6 (6)
O1—C2—C3—C4	−175.0 (12)	N1—C17—C18—O5	70.0 (12)
C1—C2—C3—C4	4.6 (19)	Mn1ii—O6—C19—C20	159.0 (7)
O1—C2—C3—O2	2.9 (17)	O6—C19—C20—N2	−65.1 (13)
C1—C2—C3—O2	−177.5 (11)	C15—N2—C20—C19	97.8 (13)
C8—O2—C3—C4	−31.1 (19)	Mn1—N2—C20—C19	−79.8 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···I1Aiii	0.86	2.86	3.488 (8)	131

Table 1

Selected bond lengths (Å)

Mn1—O3	1.829 (8)
Mn1—O1	1.849 (8)
Mn1—N1	2.035 (10)
Mn1—N2	2.061 (9)
Mn1—O6i	2.247 (8)
Mn1—O5ii	2.315 (8)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯I1A iii	0.86	2.86	3.488 (8)	131

Symmetry code: (iii) .