(4-Carb-oxy-2-sulfonato-benzoato-κO,O)bis-(1,10-phenanthroline-κN,N')manganese(II).

In the title complex, [Mn(C(8)H(4)O(7)S)(C(12)H(8)N(2))(2)], the Mn(II) atom is chelated by one 4-carb-oxy-2-sulfonato-benzoate anion and two phenathroline (phen) ligands in a distorted octa-hedral MnN(4)O(2) geometry. The benzene ring of the 4-carb-oxy-2-sulfonato-benzoate anion is twisted with respect to the two phen ring systems at dihedral angles of 66.38 (9) and 53.56 (9)°. In the crystal, inter-molecular O-H⋯O and C-H⋯O hydrogen bonding links the mol-ecules into chains running parallel to [100]. Inter-molecular π-π stacking is also observed between parallel phen ring systems, the face-to-face distance being 3.432 (6) Å.

Related literature

The 4-carb­oxy-2-sulfonato­benzoate anion has been used to construct coordination polymers through both carboxyl and sulfonate groups, see: Horike et al. (2006 ▶); Xiao et al. (2007 ▶).

Experimental

Crystal data

[Mn(C8H4O7S)(C12H8N2)2]

M = 659.52

Triclinic,

a = 9.490 (2) Å

b = 9.688 (2) Å

c = 16.842 (4) Å

α = 73.294 (4)°

β = 89.016 (4)°

γ = 70.159 (3)°

V = 1389.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.61 mm−1

T = 298 K

0.35 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.815, T max = 0.898

6937 measured reflections

4883 independent reflections

4344 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.07

4883 reflections

407 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.57 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023743/xu2781sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023743/xu2781Isup2.hkl

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

[Mn(C8H4O7S)(C12H8N2)2]	Z = 2
Mr = 659.52	F(000) = 674
Triclinic, P1	Dx = 1.576 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.490 (2) Å	Cell parameters from 1000 reflections
b = 9.688 (2) Å	θ = 2.3–28.1°
c = 16.842 (4) Å	µ = 0.61 mm−1
α = 73.294 (4)°	T = 298 K
β = 89.016 (4)°	Block, yellow
γ = 70.159 (3)°	0.35 × 0.22 × 0.18 mm
V = 1389.6 (5) Å3

Bruker SMART APEXII CCD diffractometer	4883 independent reflections
Radiation source: fine-focus sealed tube	4344 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scan	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→8
Tmin = 0.815, Tmax = 0.898	k = −11→11
6937 measured reflections	l = −20→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.1828P] where P = (Fo2 + 2Fc2)/3
4883 reflections	(Δ/σ)max = 0.001
407 parameters	Δρmax = 0.47 e Å−3
1 restraint	Δρmin = −0.56 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	0.81303 (3)	0.62093 (3)	0.736333 (18)	0.03308 (12)
S1	0.56855 (5)	0.51204 (6)	0.67785 (3)	0.03438 (15)
O1	0.89461 (15)	0.38212 (16)	0.77751 (10)	0.0426 (4)
O2	0.99042 (17)	0.1388 (2)	0.78338 (16)	0.0720 (6)
O3	0.58796 (16)	0.60968 (16)	0.72599 (10)	0.0419 (3)
O4	0.68197 (19)	0.4882 (2)	0.62139 (10)	0.0553 (4)
O5	0.41600 (17)	0.56635 (19)	0.64207 (10)	0.0492 (4)
O6	0.3320 (2)	0.0085 (2)	0.89832 (14)	0.0753 (6)
O7	0.23792 (19)	0.1821 (2)	0.77621 (14)	0.0731 (6)
H7	0.1642	0.1563	0.7867	0.110*
N1	0.75417 (18)	0.6487 (2)	0.86416 (10)	0.0360 (4)
N2	1.00468 (19)	0.6749 (2)	0.79177 (11)	0.0377 (4)
N3	0.93871 (19)	0.6367 (2)	0.62082 (10)	0.0359 (4)
N4	0.7026 (2)	0.8611 (2)	0.65126 (11)	0.0409 (4)
C1	0.6354 (3)	0.6297 (3)	0.90112 (14)	0.0454 (5)
H1	0.5646	0.6122	0.8715	0.055*
C2	0.6108 (3)	0.6344 (3)	0.98204 (15)	0.0501 (6)
H2	0.5251	0.6211	1.0055	0.060*
C3	0.7132 (3)	0.6585 (3)	1.02633 (14)	0.0481 (6)
H3	0.6996	0.6590	1.0811	0.058*
C4	0.8391 (2)	0.6827 (2)	0.98951 (13)	0.0401 (5)
C5	0.9479 (3)	0.7165 (3)	1.03036 (15)	0.0518 (6)
H5	0.9377	0.7201	1.0848	0.062*
C6	1.0646 (3)	0.7433 (3)	0.99153 (16)	0.0519 (6)
H6	1.1319	0.7690	1.0188	0.062*
C7	1.0876 (2)	0.7330 (2)	0.90899 (14)	0.0407 (5)
C8	1.2103 (3)	0.7554 (3)	0.86739 (16)	0.0484 (6)
H8	1.2783	0.7844	0.8918	0.058*
C9	1.2297 (3)	0.7346 (3)	0.79113 (16)	0.0511 (6)
H9	1.3114	0.7480	0.7629	0.061*
C10	1.1254 (3)	0.6930 (3)	0.75616 (15)	0.0458 (5)
H10	1.1411	0.6767	0.7044	0.055*
C11	0.9859 (2)	0.6951 (2)	0.86801 (12)	0.0340 (4)
C12	0.8563 (2)	0.6745 (2)	0.90764 (12)	0.0339 (4)
C13	1.0580 (2)	0.5287 (3)	0.60794 (14)	0.0432 (5)
H13	1.0930	0.4332	0.6482	0.052*
C14	1.1337 (3)	0.5519 (3)	0.53646 (15)	0.0513 (6)
H14	1.2197	0.4744	0.5305	0.062*
C15	1.0812 (3)	0.6879 (3)	0.47598 (15)	0.0517 (6)
H15	1.1297	0.7038	0.4275	0.062*
C16	0.9538 (3)	0.8046 (3)	0.48635 (14)	0.0463 (5)
C17	0.8901 (3)	0.9513 (3)	0.42570 (16)	0.0628 (7)
H17	0.9320	0.9708	0.3752	0.075*
C18	0.7714 (3)	1.0617 (3)	0.43993 (16)	0.0652 (8)
H18	0.7325	1.1564	0.3993	0.078*
C19	0.7035 (3)	1.0363 (3)	0.51642 (15)	0.0508 (6)
C20	0.5795 (3)	1.1480 (3)	0.53439 (17)	0.0662 (8)
H20	0.5381	1.2451	0.4960	0.079*
C21	0.5203 (3)	1.1138 (3)	0.60796 (17)	0.0673 (8)
H21	0.4373	1.1867	0.6204	0.081*
C22	0.5843 (3)	0.9696 (3)	0.66442 (16)	0.0545 (6)
H22	0.5416	0.9478	0.7145	0.065*
C23	0.7610 (2)	0.8935 (2)	0.57700 (12)	0.0380 (5)
C24	0.8874 (2)	0.7739 (2)	0.56166 (12)	0.0363 (4)
C25	0.8833 (2)	0.2560 (2)	0.78317 (14)	0.0385 (5)
C26	0.7340 (2)	0.2323 (2)	0.79683 (13)	0.0345 (4)
C27	0.5951 (2)	0.3317 (2)	0.75298 (12)	0.0308 (4)
C28	0.4700 (2)	0.2891 (2)	0.76675 (13)	0.0348 (4)
H28	0.3795	0.3531	0.7356	0.042*
C29	0.4756 (2)	0.1545 (2)	0.82534 (14)	0.0384 (5)
C30	0.6098 (2)	0.0612 (3)	0.87331 (16)	0.0477 (6)
H30	0.6137	−0.0260	0.9161	0.057*
C31	0.7366 (2)	0.0984 (3)	0.85731 (16)	0.0471 (6)
H31	0.8272	0.0322	0.8878	0.057*
C32	0.3415 (2)	0.1064 (3)	0.83696 (16)	0.0459 (5)

	U11	U22	U33	U12	U13	U23
Mn1	0.03048 (19)	0.03700 (19)	0.03069 (19)	−0.01261 (14)	0.00304 (13)	−0.00756 (14)
S1	0.0258 (3)	0.0387 (3)	0.0326 (3)	−0.0097 (2)	−0.00071 (19)	−0.0034 (2)
O1	0.0307 (8)	0.0364 (8)	0.0575 (9)	−0.0123 (6)	−0.0042 (7)	−0.0083 (7)
O2	0.0222 (8)	0.0439 (9)	0.151 (2)	−0.0099 (7)	0.0107 (10)	−0.0330 (11)
O3	0.0327 (8)	0.0383 (8)	0.0519 (9)	−0.0108 (6)	−0.0001 (6)	−0.0109 (7)
O4	0.0495 (10)	0.0676 (11)	0.0433 (9)	−0.0189 (9)	0.0170 (7)	−0.0111 (8)
O5	0.0350 (8)	0.0501 (9)	0.0493 (9)	−0.0120 (7)	−0.0151 (7)	0.0023 (7)
O6	0.0592 (12)	0.0700 (13)	0.0938 (15)	−0.0415 (10)	0.0020 (11)	0.0027 (12)
O7	0.0289 (9)	0.0722 (12)	0.1011 (15)	−0.0260 (9)	−0.0064 (9)	0.0102 (11)
N1	0.0301 (9)	0.0414 (9)	0.0343 (9)	−0.0116 (7)	0.0020 (7)	−0.0092 (8)
N2	0.0344 (9)	0.0430 (10)	0.0366 (9)	−0.0152 (8)	0.0044 (7)	−0.0113 (8)
N3	0.0336 (9)	0.0411 (9)	0.0333 (8)	−0.0138 (8)	0.0033 (6)	−0.0108 (8)
N4	0.0425 (10)	0.0407 (10)	0.0359 (9)	−0.0115 (8)	0.0067 (8)	−0.0099 (8)
C1	0.0388 (12)	0.0560 (14)	0.0414 (12)	−0.0178 (10)	0.0063 (9)	−0.0132 (11)
C2	0.0450 (13)	0.0572 (14)	0.0450 (13)	−0.0169 (11)	0.0163 (10)	−0.0122 (11)
C3	0.0543 (14)	0.0476 (13)	0.0326 (11)	−0.0073 (11)	0.0060 (10)	−0.0104 (10)
C4	0.0416 (12)	0.0364 (11)	0.0323 (11)	−0.0021 (9)	−0.0028 (9)	−0.0089 (9)
C5	0.0530 (15)	0.0560 (14)	0.0405 (13)	−0.0058 (12)	−0.0063 (11)	−0.0208 (11)
C6	0.0465 (14)	0.0579 (14)	0.0522 (14)	−0.0107 (11)	−0.0104 (11)	−0.0263 (12)
C7	0.0360 (11)	0.0347 (10)	0.0458 (12)	−0.0056 (9)	−0.0069 (9)	−0.0114 (10)
C8	0.0380 (12)	0.0474 (13)	0.0619 (15)	−0.0171 (10)	−0.0083 (11)	−0.0161 (12)
C9	0.0381 (12)	0.0605 (15)	0.0573 (15)	−0.0236 (11)	0.0048 (11)	−0.0140 (12)
C10	0.0406 (12)	0.0589 (14)	0.0428 (12)	−0.0245 (11)	0.0075 (10)	−0.0140 (11)
C11	0.0305 (10)	0.0301 (10)	0.0350 (11)	−0.0043 (8)	−0.0036 (8)	−0.0074 (8)
C12	0.0334 (10)	0.0292 (10)	0.0320 (10)	−0.0045 (8)	−0.0019 (8)	−0.0059 (8)
C13	0.0381 (12)	0.0438 (12)	0.0434 (12)	−0.0092 (10)	0.0002 (9)	−0.0128 (10)
C14	0.0375 (12)	0.0606 (15)	0.0562 (15)	−0.0112 (11)	0.0110 (11)	−0.0256 (13)
C15	0.0488 (14)	0.0632 (15)	0.0464 (14)	−0.0217 (12)	0.0159 (11)	−0.0195 (12)
C16	0.0493 (13)	0.0534 (13)	0.0375 (12)	−0.0212 (11)	0.0118 (10)	−0.0119 (10)
C17	0.0760 (19)	0.0614 (16)	0.0414 (14)	−0.0214 (14)	0.0188 (13)	−0.0049 (12)
C18	0.081 (2)	0.0527 (15)	0.0425 (14)	−0.0143 (14)	0.0095 (13)	0.0031 (12)
C19	0.0591 (15)	0.0430 (13)	0.0409 (13)	−0.0124 (11)	0.0030 (11)	−0.0052 (10)
C20	0.081 (2)	0.0426 (13)	0.0489 (15)	0.0014 (13)	0.0021 (14)	−0.0019 (12)
C21	0.0695 (18)	0.0518 (15)	0.0547 (16)	0.0075 (13)	0.0079 (13)	−0.0119 (13)
C22	0.0542 (15)	0.0508 (14)	0.0454 (13)	−0.0039 (12)	0.0125 (11)	−0.0127 (11)
C23	0.0405 (11)	0.0396 (11)	0.0326 (11)	−0.0148 (9)	0.0026 (9)	−0.0079 (9)
C24	0.0355 (11)	0.0423 (11)	0.0344 (11)	−0.0176 (9)	0.0036 (8)	−0.0112 (9)
C25	0.0213 (9)	0.0388 (11)	0.0514 (13)	−0.0086 (9)	−0.0034 (8)	−0.0093 (10)
C26	0.0236 (10)	0.0334 (10)	0.0440 (11)	−0.0078 (8)	0.0001 (8)	−0.0100 (9)
C27	0.0232 (9)	0.0325 (10)	0.0342 (10)	−0.0076 (8)	0.0018 (7)	−0.0088 (8)
C28	0.0222 (9)	0.0357 (10)	0.0430 (11)	−0.0065 (8)	0.0001 (8)	−0.0107 (9)
C29	0.0266 (10)	0.0348 (10)	0.0526 (13)	−0.0095 (8)	0.0055 (9)	−0.0128 (10)
C30	0.0354 (12)	0.0349 (11)	0.0628 (15)	−0.0121 (9)	0.0012 (10)	0.0000 (11)
C31	0.0288 (11)	0.0376 (11)	0.0615 (15)	−0.0071 (9)	−0.0098 (10)	0.0004 (11)
C32	0.0298 (11)	0.0360 (11)	0.0712 (16)	−0.0117 (9)	0.0082 (11)	−0.0147 (11)

Mn1—O1	2.0769 (15)	C8—C9	1.356 (4)
Mn1—O3	2.1878 (15)	C8—H8	0.9300
Mn1—N1	2.2824 (17)	C9—C10	1.384 (3)
Mn1—N2	2.3321 (18)	C9—H9	0.9300
Mn1—N3	2.2592 (17)	C10—H10	0.9300
Mn1—N4	2.2458 (18)	C11—C12	1.435 (3)
S1—O4	1.4279 (16)	C13—C14	1.393 (3)
S1—O5	1.4375 (15)	C13—H13	0.9300
S1—O3	1.4664 (16)	C14—C15	1.350 (3)
S1—C27	1.777 (2)	C14—H14	0.9300
O1—C25	1.240 (2)	C15—C16	1.396 (3)
O2—C25	1.240 (3)	C15—H15	0.9300
O6—C32	1.211 (3)	C16—C24	1.407 (3)
O7—C32	1.290 (3)	C16—C17	1.425 (4)
O7—H7	0.8200	C17—C18	1.338 (4)
N1—C1	1.321 (3)	C17—H17	0.9300
N1—C12	1.354 (3)	C18—C19	1.425 (4)
N2—C10	1.325 (3)	C18—H18	0.9300
N2—C11	1.353 (3)	C19—C23	1.395 (3)
N3—C13	1.320 (3)	C19—C20	1.400 (4)
N3—C24	1.346 (3)	C20—C21	1.352 (4)
N4—C22	1.319 (3)	C20—H20	0.9300
N4—C23	1.356 (3)	C21—C22	1.380 (4)
C1—C2	1.390 (3)	C21—H21	0.9300
C1—H1	0.9300	C22—H22	0.9300
C2—C3	1.355 (4)	C23—C24	1.437 (3)
C2—H2	0.9300	C25—C26	1.514 (3)
C3—C4	1.396 (3)	C26—C31	1.393 (3)
C3—H3	0.9300	C26—C27	1.404 (3)
C4—C12	1.408 (3)	C27—C28	1.379 (3)
C4—C5	1.425 (3)	C28—C29	1.376 (3)
C5—C6	1.339 (4)	C28—H28	0.9300
C5—H5	0.9300	C29—C30	1.388 (3)
C6—C7	1.430 (3)	C29—C32	1.489 (3)
C6—H6	0.9300	C30—C31	1.370 (3)
C7—C8	1.396 (3)	C30—H30	0.9300
C7—C11	1.397 (3)	C31—H31	0.9300
O1—Mn1—O3	87.57 (6)	N2—C11—C7	122.68 (19)
O1—Mn1—N4	159.48 (7)	N2—C11—C12	117.70 (18)
O3—Mn1—N4	83.33 (6)	C7—C11—C12	119.62 (19)
O1—Mn1—N3	94.44 (6)	N1—C12—C4	122.37 (19)
O3—Mn1—N3	117.20 (6)	N1—C12—C11	118.32 (18)
N4—Mn1—N3	73.72 (6)	C4—C12—C11	119.30 (19)
O1—Mn1—N1	94.95 (6)	N3—C13—C14	122.7 (2)
O3—Mn1—N1	84.76 (6)	N3—C13—H13	118.7
N4—Mn1—N1	102.46 (6)	C14—C13—H13	118.7
N3—Mn1—N1	156.45 (6)	C15—C14—C13	119.4 (2)
O1—Mn1—N2	101.05 (6)	C15—C14—H14	120.3
O3—Mn1—N2	155.60 (6)	C13—C14—H14	120.3
N4—Mn1—N2	94.70 (7)	C14—C15—C16	119.8 (2)
N3—Mn1—N2	85.15 (6)	C14—C15—H15	120.1
N1—Mn1—N2	71.87 (6)	C16—C15—H15	120.1
O4—S1—O5	115.77 (11)	C15—C16—C24	117.2 (2)
O4—S1—O3	111.31 (10)	C15—C16—C17	123.7 (2)
O5—S1—O3	110.92 (10)	C24—C16—C17	119.2 (2)
O4—S1—C27	107.73 (10)	C18—C17—C16	121.4 (2)
O5—S1—C27	105.52 (9)	C18—C17—H17	119.3
O3—S1—C27	104.76 (9)	C16—C17—H17	119.3
C25—O1—Mn1	151.70 (14)	C17—C18—C19	121.0 (2)
S1—O3—Mn1	116.54 (8)	C17—C18—H18	119.5
C32—O7—H7	109.5	C19—C18—H18	119.5
C1—N1—C12	117.95 (18)	C23—C19—C20	117.4 (2)
C1—N1—Mn1	125.22 (15)	C23—C19—C18	119.4 (2)
C12—N1—Mn1	116.60 (13)	C20—C19—C18	123.2 (2)
C10—N2—C11	117.11 (18)	C21—C20—C19	119.5 (2)
C10—N2—Mn1	127.55 (15)	C21—C20—H20	120.3
C11—N2—Mn1	115.29 (13)	C19—C20—H20	120.3
C13—N3—C24	118.33 (18)	C20—C21—C22	119.3 (2)
C13—N3—Mn1	126.69 (15)	C20—C21—H21	120.3
C24—N3—Mn1	114.92 (13)	C22—C21—H21	120.3
C22—N4—C23	117.38 (19)	N4—C22—C21	123.7 (2)
C22—N4—Mn1	127.03 (16)	N4—C22—H22	118.2
C23—N4—Mn1	115.51 (13)	C21—C22—H22	118.2
N1—C1—C2	123.3 (2)	N4—C23—C19	122.7 (2)
N1—C1—H1	118.4	N4—C23—C24	117.44 (19)
C2—C1—H1	118.4	C19—C23—C24	119.82 (19)
C3—C2—C1	119.2 (2)	N3—C24—C16	122.51 (19)
C3—C2—H2	120.4	N3—C24—C23	118.39 (18)
C1—C2—H2	120.4	C16—C24—C23	119.1 (2)
C2—C3—C4	119.8 (2)	O1—C25—O2	124.36 (19)
C2—C3—H3	120.1	O1—C25—C26	120.81 (18)
C4—C3—H3	120.1	O2—C25—C26	114.69 (18)
C3—C4—C12	117.4 (2)	C31—C26—C27	117.82 (18)
C3—C4—C5	123.2 (2)	C31—C26—C25	116.49 (18)
C12—C4—C5	119.4 (2)	C27—C26—C25	125.68 (18)
C6—C5—C4	121.0 (2)	C28—C27—C26	119.48 (18)
C6—C5—H5	119.5	C28—C27—S1	116.47 (15)
C4—C5—H5	119.5	C26—C27—S1	124.05 (15)
C5—C6—C7	121.3 (2)	C29—C28—C27	121.75 (18)
C5—C6—H6	119.4	C29—C28—H28	119.1
C7—C6—H6	119.4	C27—C28—H28	119.1
C8—C7—C11	117.7 (2)	C28—C29—C30	119.05 (19)
C8—C7—C6	123.0 (2)	C28—C29—C32	121.21 (19)
C11—C7—C6	119.3 (2)	C30—C29—C32	119.7 (2)
C9—C8—C7	119.7 (2)	C31—C30—C29	119.6 (2)
C9—C8—H8	120.2	C31—C30—H30	120.2
C7—C8—H8	120.2	C29—C30—H30	120.2
C8—C9—C10	118.7 (2)	C30—C31—C26	122.0 (2)
C8—C9—H9	120.7	C30—C31—H31	119.0
C10—C9—H9	120.7	C26—C31—H31	119.0
N2—C10—C9	124.1 (2)	O6—C32—O7	124.7 (2)
N2—C10—H10	118.0	O6—C32—C29	122.5 (2)
C9—C10—H10	118.0	O7—C32—C29	112.8 (2)
O3—Mn1—O1—C25	22.0 (3)	C1—N1—C12—C4	−0.6 (3)
N4—Mn1—O1—C25	−41.6 (4)	Mn1—N1—C12—C4	−175.35 (15)
N3—Mn1—O1—C25	−95.1 (3)	C1—N1—C12—C11	179.93 (19)
N1—Mn1—O1—C25	106.6 (3)	Mn1—N1—C12—C11	5.1 (2)
N2—Mn1—O1—C25	179.0 (3)	C3—C4—C12—N1	1.9 (3)
O4—S1—O3—Mn1	−21.97 (13)	C5—C4—C12—N1	−177.40 (19)
O5—S1—O3—Mn1	−152.41 (9)	C3—C4—C12—C11	−178.60 (18)
C27—S1—O3—Mn1	94.20 (10)	C5—C4—C12—C11	2.1 (3)
O1—Mn1—O3—S1	−52.43 (10)	N2—C11—C12—N1	−5.4 (3)
N4—Mn1—O3—S1	109.14 (10)	C7—C11—C12—N1	175.34 (18)
N3—Mn1—O3—S1	41.31 (11)	N2—C11—C12—C4	175.11 (18)
N1—Mn1—O3—S1	−147.63 (10)	C7—C11—C12—C4	−4.2 (3)
N2—Mn1—O3—S1	−164.19 (11)	C24—N3—C13—C14	1.0 (3)
O1—Mn1—N1—C1	−76.97 (18)	Mn1—N3—C13—C14	−176.08 (17)
O3—Mn1—N1—C1	10.13 (18)	N3—C13—C14—C15	−2.5 (4)
N4—Mn1—N1—C1	92.10 (18)	C13—C14—C15—C16	1.3 (4)
N3—Mn1—N1—C1	169.89 (17)	C14—C15—C16—C24	1.0 (4)
N2—Mn1—N1—C1	−176.99 (19)	C14—C15—C16—C17	−179.7 (3)
O1—Mn1—N1—C12	97.39 (14)	C15—C16—C17—C18	−177.3 (3)
O3—Mn1—N1—C12	−175.52 (14)	C24—C16—C17—C18	2.0 (4)
N4—Mn1—N1—C12	−93.55 (14)	C16—C17—C18—C19	−0.3 (5)
N3—Mn1—N1—C12	−15.7 (2)	C17—C18—C19—C23	−0.7 (4)
N2—Mn1—N1—C12	−2.64 (13)	C17—C18—C19—C20	179.8 (3)
O1—Mn1—N2—C10	90.70 (19)	C23—C19—C20—C21	−0.6 (4)
O3—Mn1—N2—C10	−160.28 (17)	C18—C19—C20—C21	179.0 (3)
N4—Mn1—N2—C10	−76.07 (19)	C19—C20—C21—C22	0.7 (5)
N3—Mn1—N2—C10	−2.88 (19)	C23—N4—C22—C21	−1.7 (4)
N1—Mn1—N2—C10	−177.7 (2)	Mn1—N4—C22—C21	−178.3 (2)
O1—Mn1—N2—C11	−91.80 (15)	C20—C21—C22—N4	0.5 (5)
O3—Mn1—N2—C11	17.2 (2)	C22—N4—C23—C19	1.7 (3)
N4—Mn1—N2—C11	101.42 (14)	Mn1—N4—C23—C19	178.69 (18)
N3—Mn1—N2—C11	174.61 (15)	C22—N4—C23—C24	−178.3 (2)
N1—Mn1—N2—C11	−0.17 (13)	Mn1—N4—C23—C24	−1.4 (2)
O1—Mn1—N3—C13	−20.27 (18)	C20—C19—C23—N4	−0.6 (4)
O3—Mn1—N3—C13	−109.82 (17)	C18—C19—C23—N4	179.8 (2)
N4—Mn1—N3—C13	176.81 (19)	C20—C19—C23—C24	179.4 (2)
N1—Mn1—N3—C13	93.0 (2)	C18—C19—C23—C24	−0.1 (4)
N2—Mn1—N3—C13	80.47 (18)	C13—N3—C24—C16	1.5 (3)
O1—Mn1—N3—C24	162.55 (14)	Mn1—N3—C24—C16	178.94 (17)
O3—Mn1—N3—C24	73.01 (15)	C13—N3—C24—C23	−177.63 (19)
N4—Mn1—N3—C24	−0.37 (14)	Mn1—N3—C24—C23	−0.2 (2)
N1—Mn1—N3—C24	−84.2 (2)	C15—C16—C24—N3	−2.5 (3)
N2—Mn1—N3—C24	−96.71 (14)	C17—C16—C24—N3	178.1 (2)
O1—Mn1—N4—C22	120.9 (2)	C15—C16—C24—C23	176.6 (2)
O3—Mn1—N4—C22	56.7 (2)	C17—C16—C24—C23	−2.7 (3)
N3—Mn1—N4—C22	177.6 (2)	N4—C23—C24—N3	1.1 (3)
N1—Mn1—N4—C22	−26.5 (2)	C19—C23—C24—N3	−179.0 (2)
N2—Mn1—N4—C22	−98.9 (2)	N4—C23—C24—C16	−178.1 (2)
O1—Mn1—N4—C23	−55.7 (3)	C19—C23—C24—C16	1.8 (3)
O3—Mn1—N4—C23	−119.97 (16)	Mn1—O1—C25—O2	144.8 (3)
N3—Mn1—N4—C23	0.93 (15)	Mn1—O1—C25—C26	−39.7 (4)
N1—Mn1—N4—C23	156.92 (15)	O1—C25—C26—C31	−134.3 (2)
N2—Mn1—N4—C23	84.47 (15)	O2—C25—C26—C31	41.6 (3)
C12—N1—C1—C2	−0.2 (3)	O1—C25—C26—C27	46.9 (3)
Mn1—N1—C1—C2	174.10 (18)	O2—C25—C26—C27	−137.2 (2)
N1—C1—C2—C3	−0.5 (4)	C31—C26—C27—C28	−4.6 (3)
C1—C2—C3—C4	1.9 (4)	C25—C26—C27—C28	174.23 (19)
C2—C3—C4—C12	−2.5 (3)	C31—C26—C27—S1	176.47 (17)
C2—C3—C4—C5	176.8 (2)	C25—C26—C27—S1	−4.7 (3)
C3—C4—C5—C6	−178.0 (2)	O4—S1—C27—C28	−129.68 (16)
C12—C4—C5—C6	1.2 (3)	O5—S1—C27—C28	−5.45 (18)
C4—C5—C6—C7	−2.5 (4)	O3—S1—C27—C28	111.71 (16)
C5—C6—C7—C8	−178.0 (2)	O4—S1—C27—C26	49.3 (2)
C5—C6—C7—C11	0.3 (4)	O5—S1—C27—C26	173.55 (17)
C11—C7—C8—C9	−2.4 (3)	O3—S1—C27—C26	−69.29 (18)
C6—C7—C8—C9	176.0 (2)	C26—C27—C28—C29	3.1 (3)
C7—C8—C9—C10	0.7 (4)	S1—C27—C28—C29	−177.84 (16)
C11—N2—C10—C9	−1.7 (3)	C27—C28—C29—C30	1.7 (3)
Mn1—N2—C10—C9	175.73 (18)	C27—C28—C29—C32	−177.2 (2)
C8—C9—C10—N2	1.5 (4)	C28—C29—C30—C31	−5.0 (3)
C10—N2—C11—C7	−0.1 (3)	C32—C29—C30—C31	174.0 (2)
Mn1—N2—C11—C7	−177.91 (15)	C29—C30—C31—C26	3.5 (4)
C10—N2—C11—C12	−179.41 (19)	C27—C26—C31—C30	1.3 (3)
Mn1—N2—C11—C12	2.8 (2)	C25—C26—C31—C30	−177.6 (2)
C8—C7—C11—N2	2.1 (3)	C28—C29—C32—O6	−163.7 (2)
C6—C7—C11—N2	−176.2 (2)	C30—C29—C32—O6	17.3 (4)
C8—C7—C11—C12	−178.61 (19)	C28—C29—C32—O7	14.8 (3)
C6—C7—C11—C12	3.0 (3)	C30—C29—C32—O7	−164.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O2i	0.82	1.72	2.517 (3)	165
C8—H8···O6ii	0.93	2.42	3.209 (4)	142
C18—H18···O5iii	0.93	2.46	3.306 (3)	151

Table 1

Selected bond lengths (Å)

Mn1—O1	2.0769 (15)
Mn1—O3	2.1878 (15)
Mn1—N1	2.2824 (17)
Mn1—N2	2.3321 (18)
Mn1—N3	2.2592 (17)
Mn1—N4	2.2458 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O2i	0.82	1.72	2.517 (3)	165
C8—H8⋯O6ii	0.93	2.42	3.209 (4)	142
C18—H18⋯O5iii	0.93	2.46	3.306 (3)	151

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