Aqua-{2,2-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}(3-nitro-benzoato)manganese(III).

The title compound, [Mn(C(16)H(14)N(2)O(2))(C(7)H(4)NO(4))(H(2)O)], is a Jahn-Teller-distorted manganese(III) monomer with an octa-hedral geometry. The tetra-dentate Schiff base accommodates the Mn(III) ion at the centre of a nearly planar square. The axial positions are occupied by a monodentate carboxyl-ate group and a water mol-ecule. Adjacent monomers inter-act through hydrogen bonding between the noncoordinated C=O group of the carboxyl-ate and the coordinated water mol-ecule to produce chains extending parallel to the b axis.

Related literature

For related literature, see: Christou (1989 ▶); Pecoraro & Hsieh (2000 ▶); Yocum & Pecoraro (2004 ▶); Zhang & Janiak (2001 ▶); Zouni et al. (2001 ▶); Aurangzeb et al. (1994 ▶); Hulme et al. (1997 ▶).

Experimental

Crystal data

[Mn(C16H14N2O2)(n class="CellLine">C7H4NO4)(H2O)]

M = 505.36

Monoclinic,

a = 6.7297 (1) Å

b = 10.5793 (2) Å

c = 29.228 (5) Å

β = 95.188 (1)°

V = 2072.4 (4) Å3

Z = 4

Cu Kα radiation

μ = 5.66 mm−1

T = 100 (2) K

0.35 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.245, T max = 0.624

21257 measured reflections

3640 independent reflections

3492 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.11

3640 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and XSHELL (Bruker, 2004 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al. 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019715/si2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019715/si2096Isup2.hkl

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

[Mn(C16H14N2O2)(C7H4NO4)(H2O)]	F000 = 1040
Mr = 505.36	Dx = 1.620 Mg m−3
Monoclinic, P21/n	Cu Kα radiation λ = 1.54178 Å
a = 6.7297 (1) Å	Cell parameters from 256 reflections
b = 10.5793 (2) Å	θ = 9.7–70.9º
c = 29.228 (5) Å	µ = 5.66 mm−1
β = 95.188 (1)º	T = 100 (2) K
V = 2072.4 (4) Å3	Plate, brown
Z = 4	0.35 × 0.29 × 0.09 mm

Bruker SMART APEXII CCD diffractometer	3640 independent reflections
Radiation source: fine-focus sealed tube	3492 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
T = 100(2) K	θmax = 67.0º
ω and ψ scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −7→7
Tmin = 0.245, Tmax = 0.624	k = −10→12
21257 measured reflections	l = −31→34

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0418P)2 + 2.1055P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
3640 reflections	Δρmax = 0.35 e Å−3
308 parameters	Δρmin = −0.51 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.00146 (5)	0.54194 (3)	0.229187 (11)	0.01142 (12)
O1	−0.2188 (2)	0.55831 (14)	0.18400 (5)	0.0155 (3)
O2	−0.1396 (2)	0.45279 (14)	0.27355 (5)	0.0147 (3)
O3	0.0816 (2)	0.36457 (14)	0.20036 (5)	0.0171 (3)
O4	0.3542 (2)	0.32126 (15)	0.16477 (5)	0.0197 (4)
O5	0.2710 (3)	0.15274 (18)	0.00870 (6)	0.0311 (4)
O6	−0.0245 (3)	0.12490 (17)	−0.02568 (5)	0.0282 (4)
O7	−0.0810 (2)	0.73579 (15)	0.26027 (5)	0.0190 (3)
H1W	0.0052	0.7545	0.2818	0.023*
H2W	−0.1592	0.7863	0.2531	0.023*
N1	0.1747 (3)	0.63243 (16)	0.18849 (6)	0.0133 (4)
N2	0.2479 (3)	0.54511 (16)	0.27161 (6)	0.0129 (4)
N3	0.0896 (3)	0.15170 (18)	0.00848 (6)	0.0220 (5)
C1	−0.2066 (3)	0.5574 (2)	0.13906 (8)	0.0149 (5)
C2	−0.3747 (3)	0.5194 (2)	0.11019 (8)	0.0171 (5)
H2	−0.4930	0.4950	0.1233	0.020*
C3	−0.3700 (4)	0.5173 (2)	0.06299 (8)	0.0223 (5)
H3	−0.4848	0.4907	0.0442	0.027*
C4	−0.1991 (4)	0.5536 (2)	0.04252 (8)	0.0239 (5)
H4	−0.1976	0.5519	0.0101	0.029*
C5	−0.0333 (4)	0.5917 (2)	0.06989 (8)	0.0202 (5)
H5	0.0831	0.6167	0.0561	0.024*
C6	−0.0331 (3)	0.5945 (2)	0.11816 (7)	0.0150 (4)
C7	0.1445 (3)	0.63864 (19)	0.14441 (7)	0.0141 (4)
H7	0.2464	0.6748	0.1281	0.017*
C8	0.3601 (3)	0.6801 (2)	0.21297 (7)	0.0159 (5)
H8A	0.3362	0.7622	0.2278	0.019*
H8B	0.4639	0.6920	0.1914	0.019*
C9	0.4256 (3)	0.5815 (2)	0.24879 (7)	0.0153 (4)
H9A	0.4818	0.5070	0.2341	0.018*
H9B	0.5291	0.6168	0.2715	0.018*
C10	0.2631 (3)	0.5163 (2)	0.31447 (7)	0.0138 (4)
H10	0.3899	0.5276	0.3310	0.017*
C11	0.1053 (3)	0.46869 (19)	0.33948 (7)	0.0143 (4)
C12	0.1515 (4)	0.4424 (2)	0.38667 (8)	0.0173 (5)
H12	0.2813	0.4611	0.4006	0.021*
C13	0.0131 (4)	0.3906 (2)	0.41291 (7)	0.0197 (5)
H13	0.0454	0.3749	0.4447	0.024*
C14	−0.1764 (4)	0.3614 (2)	0.39192 (8)	0.0184 (5)
H14	−0.2734	0.3258	0.4098	0.022*
C15	−0.2250 (3)	0.3835 (2)	0.34569 (7)	0.0157 (4)
H15	−0.3541	0.3615	0.3322	0.019*
C16	−0.0877 (3)	0.43777 (19)	0.31824 (7)	0.0134 (4)
C17	0.1704 (3)	0.32348 (19)	0.16688 (7)	0.0142 (4)
C18	0.0387 (3)	0.26862 (19)	0.12698 (7)	0.0140 (4)
C19	−0.1613 (3)	0.2428 (2)	0.13095 (8)	0.0173 (5)
H19	−0.2185	0.2639	0.1585	0.021*
C20	−0.2791 (4)	0.1861 (2)	0.09498 (8)	0.0200 (5)
H20	−0.4151	0.1676	0.0984	0.024*
C21	−0.1988 (4)	0.1569 (2)	0.05438 (8)	0.0197 (5)
H21	−0.2780	0.1188	0.0296	0.024*
C22	−0.0006 (3)	0.1846 (2)	0.05094 (7)	0.0166 (5)
C23	0.1219 (3)	0.2390 (2)	0.08636 (7)	0.0155 (4)
H23	0.2586	0.2556	0.0830	0.019*

	U11	U22	U33	U12	U13	U23
Mn1	0.0138 (2)	0.01245 (19)	0.00759 (19)	−0.00076 (13)	−0.00106 (13)	0.00132 (12)
O1	0.0173 (8)	0.0190 (8)	0.0097 (8)	0.0005 (6)	−0.0012 (6)	0.0015 (6)
O2	0.0182 (8)	0.0155 (8)	0.0099 (7)	−0.0004 (6)	−0.0023 (6)	0.0019 (6)
O3	0.0262 (9)	0.0129 (8)	0.0121 (8)	0.0011 (6)	0.0018 (6)	−0.0013 (6)
O4	0.0206 (9)	0.0241 (9)	0.0137 (8)	−0.0041 (7)	−0.0018 (6)	0.0007 (6)
O5	0.0317 (11)	0.0424 (11)	0.0198 (9)	0.0022 (8)	0.0059 (7)	−0.0056 (8)
O6	0.0443 (11)	0.0275 (9)	0.0113 (8)	−0.0043 (8)	−0.0053 (7)	−0.0036 (7)
O7	0.0211 (9)	0.0181 (8)	0.0161 (8)	0.0047 (6)	−0.0063 (6)	−0.0028 (6)
N1	0.0163 (9)	0.0107 (9)	0.0128 (9)	0.0004 (7)	0.0004 (7)	0.0000 (7)
N2	0.0162 (10)	0.0096 (9)	0.0128 (9)	0.0004 (7)	−0.0003 (7)	−0.0009 (7)
N3	0.0357 (13)	0.0190 (10)	0.0109 (10)	0.0011 (9)	−0.0007 (8)	−0.0005 (8)
C1	0.0208 (12)	0.0104 (10)	0.0130 (11)	0.0025 (8)	−0.0016 (9)	0.0014 (8)
C2	0.0195 (12)	0.0153 (11)	0.0156 (11)	0.0006 (9)	−0.0025 (9)	0.0019 (9)
C3	0.0275 (13)	0.0222 (12)	0.0153 (12)	0.0000 (10)	−0.0081 (9)	−0.0016 (9)
C4	0.0343 (14)	0.0269 (13)	0.0096 (11)	0.0018 (10)	−0.0026 (10)	−0.0007 (9)
C5	0.0283 (13)	0.0180 (12)	0.0146 (11)	0.0027 (10)	0.0036 (9)	0.0015 (9)
C6	0.0224 (12)	0.0106 (10)	0.0117 (10)	0.0024 (9)	−0.0010 (8)	0.0009 (8)
C7	0.0201 (12)	0.0076 (10)	0.0151 (11)	0.0013 (8)	0.0042 (8)	0.0016 (8)
C8	0.0192 (11)	0.0124 (11)	0.0160 (11)	−0.0031 (8)	0.0008 (9)	−0.0005 (8)
C9	0.0142 (11)	0.0150 (11)	0.0165 (11)	−0.0004 (9)	0.0001 (8)	−0.0003 (9)
C10	0.0172 (11)	0.0099 (10)	0.0131 (11)	0.0003 (8)	−0.0042 (8)	−0.0022 (8)
C11	0.0215 (12)	0.0105 (10)	0.0106 (11)	0.0011 (8)	−0.0011 (8)	−0.0017 (8)
C12	0.0244 (12)	0.0136 (11)	0.0128 (11)	0.0005 (9)	−0.0043 (9)	−0.0009 (8)
C13	0.0337 (14)	0.0159 (11)	0.0088 (10)	−0.0018 (10)	−0.0022 (9)	0.0000 (8)
C14	0.0281 (13)	0.0134 (11)	0.0141 (11)	−0.0028 (9)	0.0046 (9)	−0.0009 (8)
C15	0.0201 (11)	0.0128 (10)	0.0140 (11)	0.0004 (9)	−0.0002 (8)	−0.0010 (8)
C16	0.0222 (12)	0.0083 (10)	0.0093 (10)	0.0026 (8)	−0.0001 (8)	−0.0011 (8)
C17	0.0230 (13)	0.0092 (10)	0.0100 (10)	−0.0020 (8)	−0.0008 (8)	0.0021 (8)
C18	0.0215 (12)	0.0091 (10)	0.0108 (10)	0.0015 (8)	−0.0024 (8)	0.0013 (8)
C19	0.0218 (12)	0.0135 (11)	0.0166 (11)	0.0022 (9)	0.0022 (9)	0.0004 (8)
C20	0.0165 (11)	0.0191 (12)	0.0237 (12)	−0.0005 (9)	−0.0024 (9)	0.0009 (9)
C21	0.0260 (13)	0.0158 (11)	0.0158 (11)	−0.0019 (9)	−0.0073 (9)	−0.0013 (9)
C22	0.0260 (12)	0.0124 (11)	0.0108 (10)	0.0019 (9)	−0.0016 (9)	−0.0003 (8)
C23	0.0191 (11)	0.0129 (10)	0.0140 (11)	−0.0006 (8)	−0.0018 (8)	0.0014 (8)

Mn1—O1	1.8879 (15)	C7—H7	0.9500
Mn1—O2	1.9113 (15)	C8—C9	1.515 (3)
Mn1—N2	1.9946 (18)	C8—H8A	0.9900
Mn1—N1	1.9980 (18)	C8—H8B	0.9900
Mn1—O3	2.1513 (15)	C9—H9A	0.9900
Mn1—O7	2.3250 (16)	C9—H9B	0.9900
O1—C1	1.324 (3)	C10—C11	1.434 (3)
O2—C16	1.331 (3)	C10—H10	0.9500
O3—C17	1.269 (3)	C11—C12	1.414 (3)
O4—C17	1.244 (3)	C11—C16	1.426 (3)
O5—N3	1.220 (3)	C12—C13	1.373 (3)
O6—N3	1.236 (3)	C12—H12	0.9500
O7—H1W	0.8400	C13—C14	1.399 (3)
O7—H2W	0.7659	C13—H13	0.9500
N1—C7	1.288 (3)	C14—C15	1.381 (3)
N1—C8	1.471 (3)	C14—H14	0.9500
N2—C10	1.284 (3)	C15—C16	1.400 (3)
N2—C9	1.472 (3)	C15—H15	0.9500
N3—C22	1.472 (3)	C17—C18	1.515 (3)
C1—C2	1.408 (3)	C18—C19	1.389 (3)
C1—C6	1.421 (3)	C18—C23	1.393 (3)
C2—C3	1.383 (3)	C19—C20	1.394 (3)
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.397 (4)	C20—C21	1.383 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.374 (3)	C21—C22	1.378 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.411 (3)	C22—C23	1.389 (3)
C5—H5	0.9500	C23—H23	0.9500
C6—C7	1.439 (3)
O1—Mn1—O2	97.25 (7)	C9—C8—H8A	110.5
O1—Mn1—N2	171.26 (7)	N1—C8—H8B	110.5
O2—Mn1—N2	91.15 (7)	C9—C8—H8B	110.5
O1—Mn1—N1	90.20 (7)	H8A—C8—H8B	108.7
O2—Mn1—N1	172.54 (7)	N2—C9—C8	107.21 (17)
N2—Mn1—N1	81.42 (7)	N2—C9—H9A	110.3
O1—Mn1—O3	91.05 (6)	C8—C9—H9A	110.3
O2—Mn1—O3	89.70 (6)	N2—C9—H9B	110.3
N2—Mn1—O3	91.40 (7)	C8—C9—H9B	110.3
N1—Mn1—O3	89.75 (7)	H9A—C9—H9B	108.5
O1—Mn1—O7	90.07 (6)	N2—C10—C11	125.7 (2)
O2—Mn1—O7	91.54 (6)	N2—C10—H10	117.2
N2—Mn1—O7	87.29 (6)	C11—C10—H10	117.2
N1—Mn1—O7	88.85 (6)	C12—C11—C16	119.4 (2)
O3—Mn1—O7	178.21 (6)	C12—C11—C10	117.3 (2)
C1—O1—Mn1	125.44 (14)	C16—C11—C10	123.1 (2)
C16—O2—Mn1	128.63 (14)	C13—C12—C11	121.5 (2)
C17—O3—Mn1	139.29 (14)	C13—C12—H12	119.2
Mn1—O7—H1W	109.5	C11—C12—H12	119.2
Mn1—O7—H2W	133.3	C12—C13—C14	118.7 (2)
H1W—O7—H2W	116.8	C12—C13—H13	120.6
C7—N1—C8	121.31 (19)	C14—C13—H13	120.6
C7—N1—Mn1	124.86 (15)	C15—C14—C13	121.2 (2)
C8—N1—Mn1	113.44 (13)	C15—C14—H14	119.4
C10—N2—C9	120.50 (19)	C13—C14—H14	119.4
C10—N2—Mn1	126.20 (16)	C14—C15—C16	121.3 (2)
C9—N2—Mn1	113.27 (13)	C14—C15—H15	119.3
O5—N3—O6	123.7 (2)	C16—C15—H15	119.3
O5—N3—C22	118.83 (19)	O2—C16—C15	118.9 (2)
O6—N3—C22	117.5 (2)	O2—C16—C11	123.2 (2)
O1—C1—C2	118.6 (2)	C15—C16—C11	117.8 (2)
O1—C1—C6	123.5 (2)	O4—C17—O3	125.8 (2)
C2—C1—C6	117.9 (2)	O4—C17—C18	118.00 (19)
C3—C2—C1	120.9 (2)	O3—C17—C18	116.17 (19)
C3—C2—H2	119.6	C19—C18—C23	119.6 (2)
C1—C2—H2	119.6	C19—C18—C17	121.01 (19)
C2—C3—C4	121.1 (2)	C23—C18—C17	119.3 (2)
C2—C3—H3	119.4	C18—C19—C20	120.8 (2)
C4—C3—H3	119.4	C18—C19—H19	119.6
C5—C4—C3	119.2 (2)	C20—C19—H19	119.6
C5—C4—H4	120.4	C21—C20—C19	120.3 (2)
C3—C4—H4	120.4	C21—C20—H20	119.9
C4—C5—C6	121.0 (2)	C19—C20—H20	119.9
C4—C5—H5	119.5	C22—C21—C20	118.1 (2)
C6—C5—H5	119.5	C22—C21—H21	121.0
C5—C6—C1	119.9 (2)	C20—C21—H21	121.0
C5—C6—C7	117.7 (2)	C21—C22—C23	123.2 (2)
C1—C6—C7	122.4 (2)	C21—C22—N3	119.2 (2)
N1—C7—C6	124.4 (2)	C23—C22—N3	117.6 (2)
N1—C7—H7	117.8	C22—C23—C18	118.1 (2)
C6—C7—H7	117.8	C22—C23—H23	121.0
N1—C8—C9	106.32 (17)	C18—C23—H23	121.0
N1—C8—H8A	110.5
O2—Mn1—O1—C1	−146.55 (16)	C2—C1—C6—C7	178.0 (2)
N2—Mn1—O1—C1	49.5 (5)	C8—N1—C7—C6	−179.76 (19)
N1—Mn1—O1—C1	33.04 (17)	Mn1—N1—C7—C6	7.9 (3)
O3—Mn1—O1—C1	−56.72 (16)	C5—C6—C7—N1	−171.5 (2)
O7—Mn1—O1—C1	121.89 (16)	C1—C6—C7—N1	10.2 (3)
O1—Mn1—O2—C16	−161.93 (17)	C7—N1—C8—C9	−136.1 (2)
N2—Mn1—O2—C16	15.66 (17)	Mn1—N1—C8—C9	37.1 (2)
N1—Mn1—O2—C16	21.3 (6)	C10—N2—C9—C8	−145.69 (19)
O3—Mn1—O2—C16	107.05 (17)	Mn1—N2—C9—C8	35.9 (2)
O7—Mn1—O2—C16	−71.66 (17)	N1—C8—C9—N2	−45.6 (2)
O1—Mn1—O3—C17	78.3 (2)	C9—N2—C10—C11	−174.05 (19)
O2—Mn1—O3—C17	175.5 (2)	Mn1—N2—C10—C11	4.1 (3)
N2—Mn1—O3—C17	−93.3 (2)	N2—C10—C11—C12	180.0 (2)
N1—Mn1—O3—C17	−11.9 (2)	N2—C10—C11—C16	5.2 (3)
O7—Mn1—O3—C17	−50.6 (19)	C16—C11—C12—C13	−1.6 (3)
O1—Mn1—N1—C7	−24.13 (18)	C10—C11—C12—C13	−176.7 (2)
O2—Mn1—N1—C7	152.7 (5)	C11—C12—C13—C14	1.2 (3)
N2—Mn1—N1—C7	158.36 (18)	C12—C13—C14—C15	0.2 (3)
O3—Mn1—N1—C7	66.92 (18)	C13—C14—C15—C16	−1.0 (3)
O7—Mn1—N1—C7	−114.20 (18)	Mn1—O2—C16—C15	171.22 (14)
O1—Mn1—N1—C8	162.98 (14)	Mn1—O2—C16—C11	−11.9 (3)
O2—Mn1—N1—C8	−20.2 (6)	C14—C15—C16—O2	177.58 (19)
N2—Mn1—N1—C8	−14.53 (14)	C14—C15—C16—C11	0.5 (3)
O3—Mn1—N1—C8	−105.98 (14)	C12—C11—C16—O2	−176.14 (19)
O7—Mn1—N1—C8	72.91 (14)	C10—C11—C16—O2	−1.4 (3)
O1—Mn1—N2—C10	152.3 (4)	C12—C11—C16—C15	0.8 (3)
O2—Mn1—N2—C10	−11.72 (18)	C10—C11—C16—C15	175.50 (19)
N1—Mn1—N2—C10	169.01 (19)	Mn1—O3—C17—O4	77.7 (3)
O3—Mn1—N2—C10	−101.45 (18)	Mn1—O3—C17—C18	−104.5 (2)
O7—Mn1—N2—C10	79.77 (18)	O4—C17—C18—C19	165.9 (2)
O1—Mn1—N2—C9	−29.4 (5)	O3—C17—C18—C19	−12.1 (3)
O2—Mn1—N2—C9	166.56 (14)	O4—C17—C18—C23	−11.5 (3)
N1—Mn1—N2—C9	−12.70 (14)	O3—C17—C18—C23	170.54 (19)
O3—Mn1—N2—C9	76.84 (14)	C23—C18—C19—C20	0.8 (3)
O7—Mn1—N2—C9	−101.95 (14)	C17—C18—C19—C20	−176.6 (2)
Mn1—O1—C1—C2	154.51 (16)	C18—C19—C20—C21	−1.2 (3)
Mn1—O1—C1—C6	−26.4 (3)	C19—C20—C21—C22	0.4 (3)
O1—C1—C2—C3	179.8 (2)	C20—C21—C22—C23	0.7 (3)
C6—C1—C2—C3	0.6 (3)	C20—C21—C22—N3	178.6 (2)
C1—C2—C3—C4	−0.5 (4)	O5—N3—C22—C21	−165.6 (2)
C2—C3—C4—C5	0.1 (4)	O6—N3—C22—C21	14.7 (3)
C3—C4—C5—C6	0.1 (4)	O5—N3—C22—C23	12.4 (3)
C4—C5—C6—C1	0.0 (3)	O6—N3—C22—C23	−167.3 (2)
C4—C5—C6—C7	−178.4 (2)	C21—C22—C23—C18	−1.0 (3)
O1—C1—C6—C5	−179.4 (2)	N3—C22—C23—C18	−178.95 (18)
C2—C1—C6—C5	−0.3 (3)	C19—C18—C23—C22	0.3 (3)
O1—C1—C6—C7	−1.1 (3)	C17—C18—C23—C22	177.69 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H2W···O2i	0.77	2.31	3.074 (2)	172
O7—H1W···O4ii	0.84	1.89	2.710 (2)	166

Mn1—O1	1.8879 (15)
Mn1—O2	1.9113 (15)
Mn1—N2	1.9946 (18)
Mn1—N1	1.9980 (18)
Mn1—O3	2.1513 (15)
Mn1—O7	2.3250 (16)

O1—Mn1—O2	97.25 (7)
O1—Mn1—N2	171.26 (7)
O2—Mn1—N2	91.15 (7)
O1—Mn1—N1	90.20 (7)
O2—Mn1—N1	172.54 (7)
N2—Mn1—N1	81.42 (7)
O1—Mn1—O3	91.05 (6)
O2—Mn1—O3	89.70 (6)
N2—Mn1—O3	91.40 (7)
N1—Mn1—O3	89.75 (7)
O1—Mn1—O7	90.07 (6)
O2—Mn1—O7	91.54 (6)
N2—Mn1—O7	87.29 (6)
N1—Mn1—O7	88.85 (6)
O3—Mn1—O7	178.21 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H2W⋯O2i	0.77	2.31	3.074 (2)	172
O7—H1W⋯O4ii	0.84	1.89	2.710 (2)	166

Symmetry codes: (i) ; (ii) .