Di-μ-nicotinamide-κN:O;κO:N-bis-[aqua-bis-(4-bromo-benzoato)-κO;κO,O'-manganese(II)].

In the centrosymmetric dinuclear title compound, [Mn(2)(C(7)H(4)BrO(2))(4)(C(6)H(6)N(2)O)(2)(H(2)O)(2)], the Mn(II) atom is coordinated by one N atom from one bridging nicotinamide ligand and one O atom from another symmetry-related bridging nicotinamide ligand, three O atoms from two 4-bromo-benzoate ligands and one water mol-ecule in a distorted octa-hedral geometry. The dihedral angles between the carboxyl-ate groups and the adjacent benzene rings are 10.89 (16) and 8.4 (2)°, while the benzene rings are oriented at a dihedral angle of 6.09 (13)°. Inter-molecular O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π inter-actions, indicated by short centroid-centroid distances [3.845 (2) Å between the benzene rings, 3.650 (2) Å between the pyridine rings and 3.700 (3) Å between the benzene and pyridine rings] further stabilize the structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For information on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (2009a ▶,b ▶); Hökelek et al. (2010a ▶,b ▶); Necefoğlu et al. (2011 ▶); Greenaway et al. (1984 ▶).

Experimental

Crystal data

[Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2]

M = 1190.18

Triclinic,

a = 7.2213 (2) Å

b = 12.1782 (3) Å

c = 13.4931 (4) Å

α = 110.038 (3)°

β = 91.206 (2)°

γ = 103.653 (2)°

V = 1076.51 (6) Å3

Z = 1

Mo Kα radiation

μ = 4.37 mm−1

T = 294 K

0.29 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.329, T max = 0.418

18469 measured reflections

5394 independent reflections

4298 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.126

S = 1.05

5394 reflections

297 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.03 e Å−3

Δρmin = −1.76 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028492/xu5272sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028492/xu5272Isup2.hkl

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

[Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2]	Z = 1
Mr = 1190.18	F(000) = 586
Triclinic, P1	Dx = 1.836 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2213 (2) Å	Cell parameters from 7870 reflections
b = 12.1782 (3) Å	θ = 2.9–28.1°
c = 13.4931 (4) Å	µ = 4.37 mm−1
α = 110.038 (3)°	T = 294 K
β = 91.206 (2)°	Block, colorless
γ = 103.653 (2)°	0.29 × 0.22 × 0.20 mm
V = 1076.51 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	5394 independent reflections
Radiation source: fine-focus sealed tube	4298 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 28.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.329, Tmax = 0.418	k = −16→16
18469 measured reflections	l = −18→17

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0463P)2 + 2.4514P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
5394 reflections	Δρmax = 2.03 e Å−3
297 parameters	Δρmin = −1.76 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0235 (13)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.03281 (7)	0.20681 (4)	0.48986 (4)	0.02469 (14)
Br1	0.08035 (10)	−0.25888 (5)	−0.16236 (4)	0.0704 (2)
Br2	−0.35117 (11)	0.46846 (7)	1.09799 (4)	0.0875 (3)
O1	−0.0971 (3)	0.0349 (2)	0.34227 (19)	0.0305 (5)
O2	0.1724 (3)	0.1626 (2)	0.33974 (19)	0.0294 (5)
O3	−0.1656 (5)	0.1988 (3)	0.5927 (3)	0.0537 (8)
O4	−0.3453 (4)	0.0368 (2)	0.6157 (2)	0.0470 (7)
O5	−0.1222 (3)	0.3095 (2)	0.4261 (2)	0.0320 (5)
O6	0.2150 (4)	0.1154 (2)	0.5439 (2)	0.0326 (5)
H6A	0.174 (7)	0.083 (5)	0.588 (3)	0.068 (17)*
H6B	0.259 (6)	0.066 (3)	0.496 (3)	0.042 (12)*
N1	0.2516 (4)	0.3847 (2)	0.5796 (2)	0.0291 (6)
N2	−0.4244 (4)	0.1935 (3)	0.3759 (3)	0.0369 (7)
H2A	−0.541 (3)	0.187 (4)	0.357 (4)	0.054 (14)*
H2B	−0.394 (7)	0.133 (3)	0.384 (4)	0.053 (13)*
C1	0.0442 (4)	0.0650 (3)	0.2952 (2)	0.0243 (6)
C2	0.0602 (5)	−0.0145 (3)	0.1855 (3)	0.0281 (7)
C3	−0.0629 (5)	−0.1295 (3)	0.1423 (3)	0.0358 (8)
H3	−0.1523	−0.1571	0.1827	0.043*
C4	−0.0537 (6)	−0.2035 (4)	0.0392 (3)	0.0439 (9)
H4	−0.1349	−0.2811	0.0106	0.053*
C5	0.0761 (6)	−0.1610 (4)	−0.0197 (3)	0.0433 (9)
C6	0.2021 (6)	−0.0479 (4)	0.0219 (3)	0.0453 (9)
H6	0.2915	−0.0212	−0.0190	0.054*
C7	0.1942 (5)	0.0256 (3)	0.1250 (3)	0.0354 (8)
H7	0.2789	0.1021	0.1538	0.043*
C8	−0.2679 (5)	0.1464 (3)	0.6458 (3)	0.0318 (7)
C9	−0.2941 (5)	0.2254 (3)	0.7544 (3)	0.0314 (7)
C10	−0.1872 (6)	0.3452 (3)	0.7977 (3)	0.0412 (9)
H10	−0.1026	0.3769	0.7574	0.049*
C11	−0.2037 (7)	0.4181 (4)	0.8993 (4)	0.0515 (11)
H11	−0.1332	0.4986	0.9273	0.062*
C12	−0.3271 (7)	0.3688 (4)	0.9580 (3)	0.0512 (11)
C13	−0.4343 (6)	0.2518 (5)	0.9188 (4)	0.0522 (11)
H13	−0.5171	0.2207	0.9602	0.063*
C14	−0.4181 (6)	0.1794 (4)	0.8158 (3)	0.0425 (9)
H14	−0.4911	0.0995	0.7881	0.051*
C15	0.2168 (5)	0.4876 (3)	0.5798 (3)	0.0291 (7)
H15	0.0945	0.4845	0.5539	0.035*
C16	0.3514 (4)	0.5991 (3)	0.6163 (2)	0.0235 (6)
C17	0.5302 (5)	0.6036 (3)	0.6579 (3)	0.0313 (7)
H17	0.6249	0.6762	0.6834	0.038*
C18	0.5661 (5)	0.4984 (3)	0.6609 (3)	0.0373 (8)
H18	0.6852	0.4998	0.6897	0.045*
C19	0.4250 (5)	0.3911 (3)	0.6212 (3)	0.0325 (7)
H19	0.4515	0.3208	0.6234	0.039*
C20	−0.2925 (4)	0.2957 (3)	0.3966 (3)	0.0252 (6)

	U11	U22	U33	U12	U13	U23
Mn1	0.0273 (2)	0.0187 (2)	0.0281 (3)	0.00505 (17)	0.00231 (18)	0.00905 (18)
Br1	0.1104 (5)	0.0750 (4)	0.0318 (2)	0.0543 (3)	0.0100 (2)	0.0063 (2)
Br2	0.1231 (6)	0.1180 (5)	0.0361 (3)	0.0877 (5)	0.0081 (3)	0.0083 (3)
O1	0.0304 (12)	0.0269 (11)	0.0325 (12)	0.0038 (9)	0.0061 (10)	0.0109 (9)
O2	0.0269 (11)	0.0266 (11)	0.0337 (12)	0.0043 (9)	0.0009 (9)	0.0114 (9)
O3	0.0640 (19)	0.0517 (17)	0.0500 (18)	0.0148 (15)	0.0300 (15)	0.0226 (14)
O4	0.0580 (18)	0.0320 (13)	0.0502 (17)	0.0133 (12)	0.0130 (14)	0.0123 (12)
O5	0.0243 (11)	0.0230 (10)	0.0482 (15)	0.0044 (9)	−0.0054 (10)	0.0138 (10)
O6	0.0429 (14)	0.0239 (11)	0.0354 (14)	0.0116 (10)	0.0044 (11)	0.0141 (10)
N1	0.0297 (14)	0.0208 (12)	0.0361 (15)	0.0041 (10)	−0.0034 (11)	0.0113 (11)
N2	0.0276 (15)	0.0221 (13)	0.060 (2)	0.0016 (11)	−0.0041 (14)	0.0175 (14)
C1	0.0263 (15)	0.0230 (13)	0.0264 (15)	0.0076 (11)	−0.0012 (12)	0.0116 (12)
C2	0.0300 (16)	0.0301 (15)	0.0274 (16)	0.0121 (13)	0.0007 (13)	0.0117 (13)
C3	0.0403 (19)	0.0303 (16)	0.0323 (18)	0.0080 (14)	0.0012 (15)	0.0065 (14)
C4	0.054 (2)	0.0332 (18)	0.038 (2)	0.0134 (17)	−0.0039 (17)	0.0047 (16)
C5	0.060 (2)	0.047 (2)	0.0288 (18)	0.034 (2)	0.0022 (17)	0.0079 (16)
C6	0.050 (2)	0.060 (3)	0.039 (2)	0.027 (2)	0.0165 (18)	0.0250 (19)
C7	0.0354 (18)	0.0396 (18)	0.0342 (19)	0.0113 (15)	0.0048 (14)	0.0157 (15)
C8	0.0300 (16)	0.0357 (17)	0.0366 (18)	0.0163 (14)	0.0073 (14)	0.0161 (14)
C9	0.0319 (17)	0.0359 (17)	0.0351 (18)	0.0183 (14)	0.0065 (14)	0.0171 (14)
C10	0.049 (2)	0.0363 (19)	0.042 (2)	0.0151 (16)	0.0051 (17)	0.0163 (16)
C11	0.070 (3)	0.040 (2)	0.044 (2)	0.025 (2)	−0.003 (2)	0.0081 (18)
C12	0.064 (3)	0.064 (3)	0.033 (2)	0.046 (2)	0.0022 (19)	0.0071 (19)
C13	0.045 (2)	0.079 (3)	0.047 (2)	0.031 (2)	0.0176 (19)	0.030 (2)
C14	0.038 (2)	0.050 (2)	0.045 (2)	0.0143 (17)	0.0127 (17)	0.0219 (18)
C15	0.0259 (15)	0.0221 (14)	0.0378 (18)	0.0033 (12)	−0.0062 (13)	0.0112 (13)
C16	0.0248 (14)	0.0196 (13)	0.0263 (15)	0.0047 (11)	0.0018 (11)	0.0092 (11)
C17	0.0259 (15)	0.0255 (15)	0.0408 (19)	0.0019 (12)	−0.0053 (13)	0.0134 (14)
C18	0.0289 (17)	0.0336 (17)	0.051 (2)	0.0064 (14)	−0.0079 (15)	0.0190 (16)
C19	0.0361 (18)	0.0255 (15)	0.0391 (19)	0.0096 (13)	−0.0021 (14)	0.0148 (14)
C20	0.0262 (15)	0.0196 (13)	0.0278 (15)	0.0053 (11)	0.0008 (12)	0.0064 (11)

Mn1—O1	2.316 (2)	C6—C5	1.377 (6)
Mn1—O2	2.237 (2)	C6—H6	0.9300
Mn1—O3	2.025 (3)	C7—C6	1.384 (6)
Mn1—C1	2.619 (3)	C7—H7	0.9300
Br1—C5	1.891 (4)	C9—C8	1.497 (5)
Br2—C12	1.901 (4)	C9—C10	1.389 (5)
O1—C1	1.260 (4)	C9—C14	1.384 (5)
O2—C1	1.265 (4)	C10—C11	1.380 (6)
O3—C8	1.257 (4)	C10—H10	0.9300
O4—C8	1.235 (4)	C11—H11	0.9300
Mn1—O5	2.217 (2)	C12—C13	1.362 (7)
O5—C20	1.239 (4)	C12—C11	1.373 (7)
Mn1—O6	2.170 (2)	C13—H13	0.9300
O6—H6A	0.845 (19)	C14—C13	1.392 (6)
O6—H6B	0.847 (19)	C14—H14	0.9300
Mn1—N1	2.272 (3)	C15—C16	1.389 (4)
N1—C15	1.334 (4)	C15—H15	0.9300
N1—C19	1.335 (4)	C16—C17	1.378 (4)
N2—H2A	0.853 (19)	C16—C20i	1.503 (4)
N2—H2B	0.857 (19)	C17—H17	0.9300
C1—C2	1.490 (5)	C18—C17	1.380 (5)
C2—C3	1.386 (5)	C18—H18	0.9300
C2—C7	1.388 (5)	C19—C18	1.379 (5)
C3—C4	1.388 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—N2	1.314 (4)
C4—H4	0.9300	C20—C16i	1.503 (4)
C5—C4	1.364 (6)
O1—Mn1—C1	28.77 (9)	C4—C5—Br1	119.1 (3)
O2—Mn1—O1	57.61 (8)	C4—C5—C6	121.6 (4)
O2—Mn1—N1	96.47 (10)	C6—C5—Br1	119.3 (3)
O2—Mn1—C1	28.85 (9)	C5—C6—C7	119.3 (4)
O3—Mn1—O1	102.93 (11)	C5—C6—H6	120.3
O3—Mn1—O2	160.32 (12)	C7—C6—H6	120.3
O3—Mn1—O5	89.12 (12)	C2—C7—H7	120.0
O3—Mn1—O6	97.50 (12)	C6—C7—C2	120.1 (4)
O3—Mn1—N1	102.86 (12)	C6—C7—H7	120.0
O3—Mn1—C1	131.68 (12)	O3—C8—C9	116.0 (3)
O5—Mn1—O1	89.54 (9)	O4—C8—O3	125.3 (4)
O5—Mn1—O2	87.89 (9)	O4—C8—C9	118.7 (3)
O5—Mn1—N1	87.93 (9)	C10—C9—C8	120.6 (3)
O5—Mn1—C1	89.17 (9)	C14—C9—C8	120.8 (3)
O6—Mn1—O1	91.37 (9)	C14—C9—C10	118.5 (4)
O6—Mn1—O2	86.68 (9)	C9—C10—H10	119.3
O6—Mn1—O5	172.93 (10)	C11—C10—C9	121.4 (4)
O6—Mn1—N1	88.18 (10)	C11—C10—H10	119.3
O6—Mn1—C1	88.26 (10)	C10—C11—H11	120.9
N1—Mn1—O1	154.04 (10)	C12—C11—C10	118.2 (4)
N1—Mn1—C1	125.32 (10)	C12—C11—H11	120.9
C1—O1—Mn1	89.05 (18)	C11—C12—Br2	118.6 (4)
C1—O2—Mn1	92.58 (19)	C13—C12—Br2	119.1 (4)
C8—O3—Mn1	152.3 (3)	C13—C12—C11	122.3 (4)
C20—O5—Mn1	134.3 (2)	C12—C13—C14	119.0 (4)
Mn1—O6—H6B	116 (3)	C12—C13—H13	120.5
Mn1—O6—H6A	117 (4)	C14—C13—H13	120.5
H6B—O6—H6A	108 (5)	C9—C14—C13	120.5 (4)
C15—N1—Mn1	118.9 (2)	C9—C14—H14	119.7
C15—N1—C19	117.4 (3)	C13—C14—H14	119.7
C19—N1—Mn1	123.1 (2)	N1—C15—C16	124.2 (3)
C20—N2—H2A	121 (3)	N1—C15—H15	117.9
C20—N2—H2B	120 (3)	C16—C15—H15	117.9
H2A—N2—H2B	119 (5)	C15—C16—C20i	117.2 (3)
O1—C1—Mn1	62.18 (17)	C17—C16—C15	117.5 (3)
O1—C1—O2	120.7 (3)	C17—C16—C20i	125.2 (3)
O1—C1—C2	119.9 (3)	C16—C17—C18	118.8 (3)
O2—C1—Mn1	58.57 (17)	C16—C17—H17	120.6
O2—C1—C2	119.4 (3)	C18—C17—H17	120.6
C2—C1—Mn1	177.4 (2)	C17—C18—H18	120.1
C3—C2—C1	119.6 (3)	C19—C18—C17	119.9 (3)
C3—C2—C7	119.4 (3)	C19—C18—H18	120.1
C7—C2—C1	121.0 (3)	N1—C19—C18	122.2 (3)
C2—C3—C4	120.4 (4)	N1—C19—H19	118.9
C2—C3—H3	119.8	C18—C19—H19	118.9
C4—C3—H3	119.8	O5—C20—N2	123.2 (3)
C3—C4—H4	120.4	O5—C20—C16i	118.5 (3)
C5—C4—C3	119.1 (4)	N2—C20—C16i	118.3 (3)
C5—C4—H4	120.4
O2—Mn1—O1—C1	1.32 (17)	C19—N1—Mn1—O1	−78.8 (4)
O3—Mn1—O1—C1	178.1 (2)	C19—N1—Mn1—O2	−75.9 (3)
O3—Mn1—O2—C1	−10.6 (4)	C19—N1—Mn1—O3	107.9 (3)
O5—Mn1—O1—C1	89.11 (19)	C19—N1—Mn1—O5	−163.5 (3)
O6—Mn1—O1—C1	−83.88 (19)	C19—N1—Mn1—O6	10.6 (3)
N1—Mn1—O1—C1	4.8 (3)	C19—N1—Mn1—C1	−76.0 (3)
O1—Mn1—O2—C1	−1.31 (17)	Mn1—N1—C15—C16	−168.9 (3)
O5—Mn1—O2—C1	−92.11 (18)	C19—N1—C15—C16	2.8 (5)
O6—Mn1—O2—C1	92.42 (18)	Mn1—N1—C19—C18	169.8 (3)
N1—Mn1—O2—C1	−179.79 (18)	C15—N1—C19—C18	−1.5 (6)
O1—Mn1—O3—C8	56.2 (7)	O1—C1—C2—C3	−10.1 (5)
O2—Mn1—O3—C8	64.3 (8)	O2—C1—C2—C3	170.3 (3)
O5—Mn1—O3—C8	145.5 (7)	O1—C1—C2—C7	168.6 (3)
O6—Mn1—O3—C8	−37.0 (7)	O2—C1—C2—C7	−10.9 (5)
N1—Mn1—O3—C8	−126.8 (6)	C1—C2—C3—C4	178.2 (3)
C1—Mn1—O3—C8	57.4 (7)	C7—C2—C3—C4	−0.6 (5)
O1—Mn1—C1—O2	177.7 (3)	C1—C2—C7—C6	−177.6 (3)
O2—Mn1—C1—O1	−177.7 (3)	C3—C2—C7—C6	1.2 (5)
O3—Mn1—C1—O1	−2.5 (3)	C2—C3—C4—C5	−1.0 (6)
O3—Mn1—C1—O2	175.22 (19)	Br1—C5—C4—C3	−177.0 (3)
O5—Mn1—C1—O1	−90.56 (18)	C6—C5—C4—C3	2.0 (6)
O5—Mn1—C1—O2	87.14 (18)	C7—C6—C5—Br1	177.6 (3)
O6—Mn1—C1—O1	96.03 (19)	C7—C6—C5—C4	−1.5 (6)
O6—Mn1—C1—O2	−86.28 (18)	C2—C7—C6—C5	−0.2 (6)
N1—Mn1—C1—O1	−177.43 (17)	C10—C9—C8—O3	−9.3 (5)
N1—Mn1—C1—O2	0.3 (2)	C10—C9—C8—O4	170.2 (3)
Mn1—O1—C1—O2	−2.3 (3)	C14—C9—C8—O3	173.9 (4)
Mn1—O1—C1—C2	178.2 (3)	C14—C9—C8—O4	−6.5 (5)
Mn1—O2—C1—O1	2.4 (3)	C8—C9—C10—C11	−177.4 (4)
Mn1—O2—C1—C2	−178.1 (2)	C14—C9—C10—C11	−0.6 (6)
Mn1—O3—C8—O4	−37.6 (9)	C8—C9—C14—C13	176.7 (4)
Mn1—O3—C8—C9	142.0 (5)	C10—C9—C14—C13	−0.2 (6)
C20—O5—Mn1—O1	55.0 (3)	C9—C10—C11—C12	1.1 (6)
C20—O5—Mn1—O2	112.6 (3)	Br2—C12—C11—C10	−180.0 (3)
C20—O5—Mn1—O3	−47.9 (3)	C13—C12—C11—C10	−0.9 (7)
C20—O5—Mn1—N1	−150.8 (3)	Br2—C12—C13—C14	179.2 (3)
C20—O5—Mn1—C1	83.8 (3)	C11—C12—C13—C14	0.2 (7)
Mn1—O5—C20—N2	−15.3 (5)	C9—C14—C13—C12	0.3 (6)
Mn1—O5—C20—C16i	164.6 (2)	N1—C15—C16—C17	−2.1 (5)
C15—N1—Mn1—O1	92.4 (3)	N1—C15—C16—C20i	175.6 (3)
C15—N1—Mn1—O2	95.3 (3)	C15—C16—C17—C18	0.2 (5)
C15—N1—Mn1—O3	−80.9 (3)	C20i—C16—C17—C18	−177.4 (3)
C15—N1—Mn1—O5	7.7 (3)	C19—C18—C17—C16	1.0 (6)
C15—N1—Mn1—O6	−178.2 (3)	N1—C19—C18—C17	−0.3 (6)
C15—N1—Mn1—C1	95.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ii	0.85 (3)	2.02 (3)	2.856 (4)	168 (5)
O6—H6A···O1iii	0.84 (5)	1.96 (6)	2.771 (4)	162 (5)
O6—H6B···O4iii	0.84 (4)	1.83 (4)	2.670 (4)	175 (4)
C15—H15···O5	0.93	2.40	3.032 (4)	125
C17—H17···O2iv	0.93	2.27	3.125 (5)	152
C19—H19···O6	0.93	2.53	3.129 (5)	123

Table 1

Selected bond lengths (Å)

Mn1—O1	2.316 (2)
Mn1—O2	2.237 (2)
Mn1—O3	2.025 (3)
Mn1—O5	2.217 (2)
Mn1—O6	2.170 (2)
Mn1—N1	2.272 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.85 (3)	2.02 (3)	2.856 (4)	168 (5)
O6—H6A⋯O1ii	0.84 (5)	1.96 (6)	2.771 (4)	162 (5)
O6—H6B⋯O4ii	0.84 (4)	1.83 (4)	2.670 (4)	175 (4)
C17—H17⋯O2iii	0.93	2.27	3.125 (5)	152

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