catena-Poly[[[aqua-manganese(III)]-μ-(E)-5-bromo-N-[2-(5-bromo-2-oxidobenzyl-idene-amino)-4-nitro-phen-yl]-2-oxidobenzamidato] N,N-dimethyl-fomamide monosolvate].

The asymmetric unit of the title complex, {[Mn(C(20)H(10)Br(2)N(3)O(5))(H(2)O)]·(CH(3))(2)NCHO}(n), consists of one Mn(III) ion, one (E)-5-bromo-N-[2-(5-bromo-2-oxidobenzyl-idene-amino)-4-nitro-phen-yl]-2-oxidobenzamidate ligand (Schiff base), one water mol-ecule and an N,N-dimethyl-formamide mol-ecule. The coordination geometry around the Mn(III) ion is a distorted octa-hedron, being surrounded by two O and two N atoms from the Schiff base, which are positioned in the equatorial plane. The water mol-ecule and the O atom of the carbonyl group from the adjacent Mn(III) complex are situated at the axial positions, leading to a polymeric chain along the c axis. In the crystal, the complex and N,N-dimethyl-formamide mol-ecules are connected via O-H⋯O, C-H⋯O and C-H⋯Br hydrogen bonds, forming a three-dimensional network.

Related literature

For details of the coordination chemistry and biological importance of manganese, see: Maneiro et al. (2003 ▶); Chandra et al. (2009 ▶); Chrisianson & Cox (1999 ▶); Ni et al. (2009 ▶); Zhang et al. (2005 ▶); Huh & Lee (2008 ▶); Pastoriza-Santos & Liz-Marzań (2009 ▶). For related structures, see: Su & Xu (2005 ▶); Ma et al. (2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Mn(C20H10Br2N3O5)(H2O)]·C3H7NO

M = 678.18

Monoclinic,

a = 11.0746 (6) Å

b = 24.9781 (13) Å

c = 9.5563 (5) Å

β = 114.658 (1)°

V = 2402.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.93 mm−1

T = 100 K

0.52 × 0.17 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.234, T max = 0.672

27005 measured reflections

8188 independent reflections

6617 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.02

8188 reflections

344 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.85 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I, an. DOI: 10.1107/S1600536812008501/is5080sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008501/is5080Isup2.hkl

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

[Mn(C20H10Br2N3O5)(H2O)]·C3H7NO	F(000) = 1344
Mr = 678.18	Dx = 1.875 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7902 reflections
a = 11.0746 (6) Å	θ = 3.2–31.8°
b = 24.9781 (13) Å	µ = 3.93 mm−1
c = 9.5563 (5) Å	T = 100 K
β = 114.658 (1)°	Block, brown
V = 2402.4 (2) Å3	0.52 × 0.17 × 0.11 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	8188 independent reflections
Radiation source: fine-focus sealed tube	6617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 31.8°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.234, Tmax = 0.672	k = −36→37
27005 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.041P)2 + 1.7977P] where P = (Fo2 + 2Fc2)/3
8188 reflections	(Δ/σ)max = 0.003
344 parameters	Δρmax = 1.85 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.32207 (3)	0.285186 (10)	1.10714 (3)	0.01283 (6)
Br1	0.39872 (2)	−0.002567 (8)	1.29527 (2)	0.02540 (6)
Br2	0.00337 (3)	0.540295 (9)	0.75613 (3)	0.03831 (8)
O1	0.19454 (14)	0.31410 (5)	0.92195 (14)	0.0161 (2)
O2	0.28189 (14)	0.21775 (5)	1.01810 (15)	0.0162 (3)
O3	0.65113 (16)	0.47920 (6)	1.64497 (17)	0.0250 (3)
O4	0.76182 (19)	0.42584 (7)	1.83364 (18)	0.0345 (4)
N1	0.37015 (15)	0.35574 (6)	1.20959 (17)	0.0132 (3)
N2	0.44814 (15)	0.25853 (6)	1.31031 (17)	0.0130 (3)
N3	0.68440 (17)	0.43404 (7)	1.69974 (19)	0.0196 (3)
C1	0.15509 (18)	0.36422 (7)	0.8920 (2)	0.0155 (3)
C2	0.0566 (2)	0.37633 (8)	0.7440 (2)	0.0207 (4)
H2	0.0211	0.3490	0.6722	0.025*
C3	0.0124 (2)	0.42798 (8)	0.7046 (2)	0.0239 (4)
H3	−0.0516	0.4355	0.6063	0.029*
C4	0.0636 (2)	0.46918 (8)	0.8124 (3)	0.0240 (4)
C5	0.1582 (2)	0.45925 (8)	0.9576 (2)	0.0212 (4)
H5	0.1906	0.4870	1.0283	0.025*
C6	0.20647 (19)	0.40668 (7)	0.9997 (2)	0.0163 (3)
C7	0.30926 (19)	0.40035 (7)	1.1515 (2)	0.0154 (3)
H7	0.3347	0.4306	1.2137	0.019*
C8	0.47310 (18)	0.35266 (7)	1.36140 (19)	0.0130 (3)
C9	0.53061 (18)	0.39672 (7)	1.4535 (2)	0.0149 (3)
H9	0.5039	0.4313	1.4178	0.018*
C10	0.62842 (19)	0.38799 (7)	1.5994 (2)	0.0157 (3)
C11	0.6734 (2)	0.33696 (8)	1.6552 (2)	0.0177 (3)
H11	0.7412	0.3324	1.7530	0.021*
C12	0.6157 (2)	0.29309 (7)	1.5628 (2)	0.0169 (3)
H12	0.6452	0.2588	1.5986	0.020*
C13	0.51269 (18)	0.30003 (7)	1.4150 (2)	0.0135 (3)
C14	0.44056 (18)	0.20846 (7)	1.3632 (2)	0.0141 (3)
C15	0.38604 (18)	0.16400 (7)	1.2496 (2)	0.0142 (3)
C16	0.41170 (19)	0.11188 (7)	1.3105 (2)	0.0162 (3)
H16	0.4619	0.1069	1.4155	0.019*
C17	0.3626 (2)	0.06804 (7)	1.2151 (2)	0.0177 (3)
C18	0.2833 (2)	0.07434 (7)	1.0590 (2)	0.0182 (3)
H18	0.2489	0.0446	0.9964	0.022*
C19	0.25639 (19)	0.12505 (7)	0.9983 (2)	0.0166 (3)
H19	0.2018	0.1294	0.8943	0.020*
C20	0.30947 (18)	0.17067 (7)	1.0900 (2)	0.0138 (3)
O6	0.47681 (14)	0.19817 (5)	1.50376 (15)	0.0162 (3)
O1W	0.15751 (15)	0.28059 (7)	1.18541 (18)	0.0203 (3)
O5	0.94801 (16)	0.27762 (6)	1.48344 (18)	0.0259 (3)
N4	0.84158 (18)	0.32089 (7)	1.2543 (2)	0.0202 (3)
C21	0.9247 (2)	0.28447 (8)	1.3460 (3)	0.0232 (4)
H21	0.9687	0.2625	1.3039	0.028*
C22	0.7663 (2)	0.35587 (9)	1.3091 (3)	0.0269 (4)
H22A	0.7843	0.3468	1.4135	0.040*
H22B	0.6731	0.3516	1.2455	0.040*
H22C	0.7915	0.3924	1.3044	0.040*
C23	0.8221 (2)	0.32762 (9)	1.0947 (2)	0.0250 (4)
H23A	0.8686	0.2998	1.0680	0.037*
H23B	0.8558	0.3619	1.0826	0.037*
H23C	0.7290	0.3255	1.0285	0.037*
H1W2	0.110 (4)	0.2602 (15)	1.142 (4)	0.051 (11)*
H2W2	0.180 (3)	0.2712 (12)	1.269 (4)	0.034 (8)*

	U11	U22	U33	U12	U13	U23
Mn1	0.01673 (13)	0.01111 (12)	0.00881 (11)	−0.00105 (9)	0.00349 (10)	−0.00144 (9)
Br1	0.03687 (12)	0.01250 (9)	0.02373 (10)	0.00229 (8)	0.00957 (9)	0.00146 (7)
Br2	0.03147 (13)	0.01713 (10)	0.04152 (14)	0.00359 (8)	−0.00934 (10)	0.00522 (9)
O1	0.0204 (6)	0.0140 (6)	0.0106 (5)	−0.0001 (5)	0.0030 (5)	−0.0002 (4)
O2	0.0241 (7)	0.0107 (6)	0.0119 (5)	−0.0022 (5)	0.0057 (5)	−0.0014 (4)
O3	0.0333 (8)	0.0129 (6)	0.0223 (7)	−0.0034 (6)	0.0050 (6)	−0.0013 (5)
O4	0.0465 (10)	0.0217 (7)	0.0162 (7)	−0.0040 (7)	−0.0059 (7)	−0.0030 (6)
N1	0.0153 (7)	0.0128 (6)	0.0105 (6)	−0.0011 (5)	0.0043 (5)	−0.0012 (5)
N2	0.0158 (7)	0.0113 (6)	0.0106 (6)	−0.0006 (5)	0.0044 (5)	−0.0018 (5)
N3	0.0230 (8)	0.0168 (7)	0.0161 (7)	−0.0034 (6)	0.0052 (6)	−0.0032 (6)
C1	0.0163 (8)	0.0155 (8)	0.0132 (7)	−0.0015 (6)	0.0047 (6)	−0.0003 (6)
C2	0.0209 (9)	0.0195 (9)	0.0151 (8)	−0.0017 (7)	0.0011 (7)	0.0001 (7)
C3	0.0203 (9)	0.0212 (9)	0.0204 (9)	0.0007 (7)	−0.0013 (8)	0.0041 (7)
C4	0.0218 (10)	0.0160 (8)	0.0261 (10)	0.0017 (7)	0.0019 (8)	0.0038 (7)
C5	0.0193 (9)	0.0146 (8)	0.0222 (9)	0.0002 (7)	0.0014 (7)	−0.0002 (7)
C6	0.0172 (8)	0.0150 (8)	0.0137 (8)	−0.0003 (6)	0.0034 (7)	−0.0005 (6)
C7	0.0170 (8)	0.0136 (7)	0.0143 (8)	0.0000 (6)	0.0050 (7)	−0.0012 (6)
C8	0.0138 (8)	0.0128 (7)	0.0107 (7)	−0.0004 (6)	0.0036 (6)	−0.0010 (6)
C9	0.0164 (8)	0.0137 (7)	0.0142 (7)	−0.0011 (6)	0.0059 (6)	−0.0014 (6)
C10	0.0186 (8)	0.0141 (8)	0.0129 (7)	−0.0038 (6)	0.0050 (7)	−0.0043 (6)
C11	0.0195 (9)	0.0167 (8)	0.0125 (7)	−0.0011 (7)	0.0024 (7)	−0.0011 (6)
C12	0.0203 (9)	0.0137 (8)	0.0138 (8)	−0.0010 (7)	0.0044 (7)	−0.0011 (6)
C13	0.0156 (8)	0.0133 (7)	0.0115 (7)	−0.0011 (6)	0.0058 (6)	−0.0019 (6)
C14	0.0150 (8)	0.0129 (7)	0.0134 (7)	−0.0003 (6)	0.0049 (6)	−0.0007 (6)
C15	0.0176 (8)	0.0135 (7)	0.0115 (7)	−0.0009 (6)	0.0059 (6)	−0.0008 (6)
C16	0.0193 (9)	0.0133 (8)	0.0152 (8)	0.0003 (6)	0.0063 (7)	0.0003 (6)
C17	0.0215 (9)	0.0113 (7)	0.0210 (9)	0.0007 (7)	0.0096 (7)	0.0009 (6)
C18	0.0222 (9)	0.0134 (8)	0.0180 (8)	−0.0036 (7)	0.0075 (7)	−0.0040 (6)
C19	0.0205 (9)	0.0150 (8)	0.0126 (7)	−0.0029 (7)	0.0052 (7)	−0.0030 (6)
C20	0.0165 (8)	0.0125 (7)	0.0134 (7)	−0.0007 (6)	0.0073 (6)	−0.0014 (6)
O6	0.0196 (6)	0.0164 (6)	0.0120 (6)	0.0000 (5)	0.0058 (5)	0.0006 (5)
O1W	0.0181 (7)	0.0288 (8)	0.0123 (6)	−0.0024 (6)	0.0046 (5)	0.0010 (6)
O5	0.0249 (8)	0.0265 (8)	0.0253 (7)	0.0055 (6)	0.0093 (6)	0.0059 (6)
N4	0.0217 (8)	0.0207 (8)	0.0197 (8)	0.0021 (6)	0.0099 (7)	0.0001 (6)
C21	0.0229 (10)	0.0222 (9)	0.0262 (10)	0.0029 (8)	0.0120 (8)	0.0009 (8)
C22	0.0294 (11)	0.0281 (10)	0.0262 (10)	0.0088 (9)	0.0146 (9)	0.0024 (8)
C23	0.0290 (11)	0.0268 (10)	0.0200 (9)	0.0002 (8)	0.0110 (8)	0.0002 (8)

Mn1—O2	1.8557 (13)	C9—H9	0.9300
Mn1—O1	1.8875 (13)	C10—C11	1.391 (3)
Mn1—N2	1.9750 (15)	C11—C12	1.385 (3)
Mn1—N1	1.9782 (15)	C11—H11	0.9300
Mn1—O1W	2.2431 (15)	C12—C13	1.408 (3)
Mn1—O6i	2.3448 (14)	C12—H12	0.9300
Br1—C17	1.8977 (18)	C14—O6	1.258 (2)
Br2—C4	1.895 (2)	C14—C15	1.493 (2)
O1—C1	1.317 (2)	C15—C16	1.406 (2)
O2—C20	1.331 (2)	C15—C20	1.412 (2)
O3—N3	1.233 (2)	C16—C17	1.383 (3)
O4—N3	1.224 (2)	C16—H16	0.9300
N1—C7	1.301 (2)	C17—C18	1.389 (3)
N1—C8	1.425 (2)	C18—C19	1.373 (3)
N2—C14	1.365 (2)	C18—H18	0.9300
N2—C13	1.410 (2)	C19—C20	1.407 (2)
N3—C10	1.460 (2)	C19—H19	0.9300
C1—C2	1.412 (3)	O6—Mn1ii	2.3448 (14)
C1—C6	1.421 (3)	O1W—H1W2	0.72 (4)
C2—C3	1.375 (3)	O1W—H2W2	0.77 (3)
C2—H2	0.9300	O5—C21	1.240 (3)
C3—C4	1.398 (3)	N4—C21	1.331 (3)
C3—H3	0.9300	N4—C22	1.448 (3)
C4—C5	1.368 (3)	N4—C23	1.458 (3)
C5—C6	1.412 (3)	C21—H21	0.9300
C5—H5	0.9300	C22—H22A	0.9600
C6—C7	1.430 (3)	C22—H22B	0.9600
C7—H7	0.9300	C22—H22C	0.9600
C8—C9	1.387 (2)	C23—H23A	0.9600
C8—C13	1.413 (2)	C23—H23B	0.9600
C9—C10	1.380 (3)	C23—H23C	0.9600
O2—Mn1—O1	88.57 (6)	C9—C10—N3	118.59 (16)
O2—Mn1—N2	94.63 (6)	C11—C10—N3	118.96 (16)
O1—Mn1—N2	175.06 (6)	C12—C11—C10	118.98 (17)
O2—Mn1—N1	177.72 (6)	C12—C11—H11	120.5
O1—Mn1—N1	93.71 (6)	C10—C11—H11	120.5
N2—Mn1—N1	83.10 (6)	C11—C12—C13	120.50 (17)
O2—Mn1—O1W	91.93 (6)	C11—C12—H12	119.8
O1—Mn1—O1W	86.45 (6)	C13—C12—H12	119.8
N2—Mn1—O1W	89.68 (6)	C12—C13—N2	125.44 (16)
N1—Mn1—O1W	88.22 (6)	C12—C13—C8	118.51 (16)
O2—Mn1—O6i	92.60 (5)	N2—C13—C8	115.98 (15)
O1—Mn1—O6i	85.96 (5)	O6—C14—N2	122.76 (16)
N2—Mn1—O6i	97.63 (6)	O6—C14—C15	118.47 (16)
N1—Mn1—O6i	87.56 (6)	N2—C14—C15	118.77 (15)
O1W—Mn1—O6i	171.06 (5)	C16—C15—C20	118.88 (16)
C1—O1—Mn1	128.16 (12)	C16—C15—C14	115.91 (15)
C20—O2—Mn1	127.29 (11)	C20—C15—C14	125.18 (16)
C7—N1—C8	122.21 (15)	C17—C16—C15	120.29 (17)
C7—N1—Mn1	124.56 (13)	C17—C16—H16	119.9
C8—N1—Mn1	113.05 (11)	C15—C16—H16	119.9
C14—N2—C13	120.16 (15)	C16—C17—C18	121.12 (17)
C14—N2—Mn1	123.06 (12)	C16—C17—Br1	120.75 (15)
C13—N2—Mn1	113.00 (11)	C18—C17—Br1	118.11 (14)
O4—N3—O3	123.46 (17)	C19—C18—C17	119.14 (17)
O4—N3—C10	118.37 (17)	C19—C18—H18	120.4
O3—N3—C10	118.17 (16)	C17—C18—H18	120.4
O1—C1—C2	117.94 (16)	C18—C19—C20	121.56 (17)
O1—C1—C6	123.76 (16)	C18—C19—H19	119.2
C2—C1—C6	118.30 (17)	C20—C19—H19	119.2
C3—C2—C1	120.85 (18)	O2—C20—C19	116.61 (16)
C3—C2—H2	119.6	O2—C20—C15	124.49 (16)
C1—C2—H2	119.6	C19—C20—C15	118.89 (16)
C2—C3—C4	120.02 (19)	C14—O6—Mn1ii	116.75 (12)
C2—C3—H3	120.0	Mn1—O1W—H1W2	110 (3)
C4—C3—H3	120.0	Mn1—O1W—H2W2	114 (2)
C5—C4—C3	121.17 (19)	H1W2—O1W—H2W2	103 (3)
C5—C4—Br2	119.20 (16)	C21—N4—C22	121.24 (18)
C3—C4—Br2	119.63 (16)	C21—N4—C23	121.86 (18)
C4—C5—C6	119.77 (18)	C22—N4—C23	116.90 (17)
C4—C5—H5	120.1	O5—C21—N4	125.0 (2)
C6—C5—H5	120.1	O5—C21—H21	117.5
C5—C6—C1	119.88 (17)	N4—C21—H21	117.5
C5—C6—C7	116.01 (16)	N4—C22—H22A	109.5
C1—C6—C7	124.10 (17)	N4—C22—H22B	109.5
N1—C7—C6	125.38 (17)	H22A—C22—H22B	109.5
N1—C7—H7	117.3	N4—C22—H22C	109.5
C6—C7—H7	117.3	H22A—C22—H22C	109.5
C9—C8—C13	121.17 (16)	H22B—C22—H22C	109.5
C9—C8—N1	124.31 (16)	N4—C23—H23A	109.5
C13—C8—N1	114.51 (15)	N4—C23—H23B	109.5
C10—C9—C8	118.35 (17)	H23A—C23—H23B	109.5
C10—C9—H9	120.8	N4—C23—H23C	109.5
C8—C9—H9	120.8	H23A—C23—H23C	109.5
C9—C10—C11	122.43 (16)	H23B—C23—H23C	109.5
O2—Mn1—O1—C1	175.97 (16)	N1—C8—C9—C10	179.15 (17)
N1—Mn1—O1—C1	−4.03 (16)	C8—C9—C10—C11	1.8 (3)
O1W—Mn1—O1—C1	83.95 (16)	C8—C9—C10—N3	−176.83 (16)
O6i—Mn1—O1—C1	−91.32 (15)	O4—N3—C10—C9	173.19 (19)
O1—Mn1—O2—C20	−162.27 (15)	O3—N3—C10—C9	−6.8 (3)
N2—Mn1—O2—C20	13.96 (16)	O4—N3—C10—C11	−5.5 (3)
O1W—Mn1—O2—C20	−75.87 (15)	O3—N3—C10—C11	174.50 (18)
O6i—Mn1—O2—C20	111.84 (15)	C9—C10—C11—C12	−1.8 (3)
O1—Mn1—N1—C7	6.45 (16)	N3—C10—C11—C12	176.82 (17)
N2—Mn1—N1—C7	−169.77 (16)	C10—C11—C12—C13	−0.3 (3)
O1W—Mn1—N1—C7	−79.88 (15)	C11—C12—C13—N2	178.99 (18)
O6i—Mn1—N1—C7	92.24 (15)	C11—C12—C13—C8	2.2 (3)
O1—Mn1—N1—C8	−178.30 (12)	C14—N2—C13—C12	27.2 (3)
N2—Mn1—N1—C8	5.48 (12)	Mn1—N2—C13—C12	−174.01 (15)
O1W—Mn1—N1—C8	95.38 (12)	C14—N2—C13—C8	−155.88 (16)
O6i—Mn1—N1—C8	−92.51 (12)	Mn1—N2—C13—C8	2.9 (2)
O2—Mn1—N2—C14	−26.70 (15)	C9—C8—C13—C12	−2.2 (3)
N1—Mn1—N2—C14	153.46 (15)	N1—C8—C13—C12	178.80 (16)
O1W—Mn1—N2—C14	65.22 (14)	C9—C8—C13—N2	−179.31 (16)
O6i—Mn1—N2—C14	−119.95 (14)	N1—C8—C13—N2	1.7 (2)
O2—Mn1—N2—C13	175.27 (12)	C13—N2—C14—O6	7.6 (3)
N1—Mn1—N2—C13	−4.57 (12)	Mn1—N2—C14—O6	−148.89 (15)
O1W—Mn1—N2—C13	−92.82 (13)	C13—N2—C14—C15	−172.84 (16)
O6i—Mn1—N2—C13	82.02 (12)	Mn1—N2—C14—C15	30.6 (2)
Mn1—O1—C1—C2	−179.45 (14)	O6—C14—C15—C16	−16.2 (3)
Mn1—O1—C1—C6	0.9 (3)	N2—C14—C15—C16	164.22 (16)
O1—C1—C2—C3	−179.07 (19)	O6—C14—C15—C20	162.02 (18)
C6—C1—C2—C3	0.6 (3)	N2—C14—C15—C20	−17.5 (3)
C1—C2—C3—C4	−0.9 (3)	C20—C15—C16—C17	0.1 (3)
C2—C3—C4—C5	0.3 (4)	C14—C15—C16—C17	178.44 (17)
C2—C3—C4—Br2	179.33 (17)	C15—C16—C17—C18	−2.4 (3)
C3—C4—C5—C6	0.7 (3)	C15—C16—C17—Br1	179.05 (14)
Br2—C4—C5—C6	−178.36 (16)	C16—C17—C18—C19	1.7 (3)
C4—C5—C6—C1	−1.0 (3)	Br1—C17—C18—C19	−179.70 (15)
C4—C5—C6—C7	177.4 (2)	C17—C18—C19—C20	1.3 (3)
O1—C1—C6—C5	−179.99 (18)	Mn1—O2—C20—C19	173.51 (13)
C2—C1—C6—C5	0.4 (3)	Mn1—O2—C20—C15	−5.8 (3)
O1—C1—C6—C7	1.8 (3)	C18—C19—C20—O2	177.07 (17)
C2—C1—C6—C7	−177.89 (18)	C18—C19—C20—C15	−3.6 (3)
C8—N1—C7—C6	179.15 (17)	C16—C15—C20—O2	−177.88 (17)
Mn1—N1—C7—C6	−6.0 (3)	C14—C15—C20—O2	3.9 (3)
C5—C6—C7—N1	−177.16 (19)	C16—C15—C20—C19	2.8 (3)
C1—C6—C7—N1	1.2 (3)	C14—C15—C20—C19	−175.36 (17)
C7—N1—C8—C9	−9.0 (3)	N2—C14—O6—Mn1ii	83.77 (19)
Mn1—N1—C8—C9	175.61 (14)	C15—C14—O6—Mn1ii	−95.75 (17)
C7—N1—C8—C13	169.94 (17)	C22—N4—C21—O5	−1.6 (3)
Mn1—N1—C8—C13	−5.44 (19)	C23—N4—C21—O5	178.2 (2)
C13—C8—C9—C10	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W2···O5iii	0.73 (4)	2.03 (4)	2.736 (2)	163 (4)
O1W—H2W2···O1ii	0.77 (3)	2.55 (3)	3.178 (2)	140 (3)
O1W—H2W2···O2ii	0.77 (3)	2.19 (3)	2.890 (2)	153 (3)
C2—H2···O5iv	0.93	2.42	3.351 (2)	175
C5—H5···O4v	0.93	2.49	3.395 (3)	166
C7—H7···O3v	0.93	2.60	3.509 (2)	167
C18—H18···Br2vi	0.93	2.83	3.449 (2)	125
C23—H23A···O5i	0.96	2.40	3.350 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W2⋯O5i	0.73 (4)	2.03 (4)	2.736 (2)	163 (4)
O1W—H2W2⋯O1ii	0.77 (3)	2.55 (3)	3.178 (2)	140 (3)
O1W—H2W2⋯O2ii	0.77 (3)	2.19 (3)	2.890 (2)	153 (3)
C2—H2⋯O5iii	0.93	2.42	3.351 (2)	175
C5—H5⋯O4iv	0.93	2.49	3.395 (3)	166
C7—H7⋯O3iv	0.93	2.60	3.509 (2)	167
C18—H18⋯Br2v	0.93	2.83	3.449 (2)	125
C23—H23A⋯O5vi	0.96	2.40	3.350 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .