Aqua-chlorido{1-[1-(4-hydroxy-phen-yl)-1H-tetra-zol-5-ylsulfan-yl]acetato}(methanol)(1,10-phenanthroline)manganese(II).

The title complex, [Mn(C(9)H(7)N(4)O(3)S)Cl(C(12)H(8)N(2))(CH(4)O)(H(2)O)], contains an Mn(II) ion six-coordinated by one O atom from the 2-[1-(4-hydroxy-phen-yl)-1H-tetra-zol-5-ylsulfan-yl]-acetate ligand, two N atoms from a chelating 1,10-phenanthroline ligand, one O atom from a methanol mol-ecule, one Cl atom and one water mol-ecule in a distorted octa-hedral coordination geometry. The existence of O-H⋯Cl, O-H⋯N and O-H⋯O hydrogen bonds further produces a two-dimensional structure.

Related literature

For general background, see: Hu et al. (2006 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

[Mn(C9H7N4O3S)Cl(C12H8N2)(CH4O)(H2O)]

M = 571.90

Triclinic,

a = 10.5565 (3) Å

b = 11.4969 (2) Å

c = 11.5931 (2) Å

α = 114.362 (1)°

β = 96.841 (1)°

γ = 103.969 (1)°

V = 1205.17 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 296 (2) K

0.34 × 0.23 × 0.11 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.806, T max = 0.916

13742 measured reflections

4186 independent reflections

3802 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.081

S = 1.07

4186 reflections

337 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038245/at2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038245/at2671Isup2.hkl

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

[Mn(C9H7N4O3S)Cl(C12H8N2)(CH4O)(H2O)]	Z = 2
Mr = 571.90	F000 = 586
Triclinic, P1	Dx = 1.576 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.5565 (3) Å	Cell parameters from 5369 reflections
b = 11.4969 (2) Å	θ = 2.0–25.0º
c = 11.5931 (2) Å	µ = 0.79 mm−1
α = 114.3620 (10)º	T = 296 (2) K
β = 96.8410 (10)º	Block, colourless
γ = 103.9690 (10)º	0.34 × 0.23 × 0.11 mm
V = 1205.17 (5) Å3

Bruker APEXII area-detector diffractometer	4186 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 296(2) K	θmax = 25.0º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.806, Tmax = 0.916	k = −13→13
13742 measured reflections	l = −13→13

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2751P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4186 reflections	Δρmax = 0.33 e Å−3
337 parameters	Δρmin = −0.27 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.19580 (2)	0.37914 (3)	0.39006 (2)	0.03039 (10)
S1	0.41984 (5)	0.76432 (5)	0.90045 (5)	0.03782 (13)
O1	0.22915 (13)	0.76112 (13)	0.71081 (14)	0.0432 (3)
O2	0.20363 (13)	0.56470 (13)	0.54313 (13)	0.0433 (3)
O3	0.30543 (16)	1.00580 (15)	1.46112 (16)	0.0506 (4)
H3B	0.322 (3)	1.0813 (18)	1.469 (3)	0.061*
O4	0.01155 (13)	0.25511 (15)	0.41066 (15)	0.0459 (3)
H4B	−0.0559 (19)	0.259 (2)	0.375 (2)	0.055*
O1W	0.36180 (14)	0.49567 (15)	0.34462 (15)	0.0436 (3)
H1WA	0.378 (2)	0.461 (2)	0.2748 (16)	0.052*
H1WB	0.4312 (19)	0.551 (2)	0.3980 (18)	0.052*
Cl1	0.34450 (5)	0.30009 (5)	0.50090 (5)	0.04618 (14)
N1	0.55547 (16)	0.73208 (15)	1.09287 (15)	0.0371 (4)
N2	0.63935 (18)	0.66518 (18)	1.11195 (17)	0.0454 (4)
N3	0.65952 (17)	0.59784 (17)	0.99986 (17)	0.0443 (4)
N4	0.59187 (15)	0.61830 (16)	0.90566 (16)	0.0376 (4)
N5	0.17387 (14)	0.21255 (14)	0.18296 (15)	0.0327 (3)
N6	0.05314 (15)	0.40551 (15)	0.24743 (15)	0.0331 (3)
C1	0.37482 (19)	0.94561 (19)	1.37606 (18)	0.0371 (4)
C2	0.3594 (2)	0.8111 (2)	1.34184 (19)	0.0401 (4)
H2A	0.3079	0.7679	1.3811	0.048*
C3	0.4201 (2)	0.74207 (19)	1.25000 (19)	0.0394 (4)
H3A	0.4083	0.6515	1.2255	0.047*
C4	0.49903 (19)	0.80822 (18)	1.19405 (18)	0.0352 (4)
C5	0.5208 (2)	0.94331 (19)	1.23160 (19)	0.0389 (4)
H5A	0.5768	0.9877	1.1961	0.047*
C6	0.45784 (19)	1.01185 (19)	1.32297 (19)	0.0382 (4)
H6A	0.4714	1.1029	1.3489	0.046*
C7	0.52702 (18)	0.70145 (17)	0.96571 (18)	0.0326 (4)
C8	0.38078 (19)	0.64340 (19)	0.72948 (18)	0.0371 (4)
H8A	0.4581	0.6597	0.6940	0.045*
H8B	0.3587	0.5526	0.7204	0.045*
C9	0.26138 (17)	0.65837 (18)	0.65563 (18)	0.0325 (4)
C10	−0.00740 (19)	0.4990 (2)	0.2799 (2)	0.0405 (4)
H10A	0.0080	0.5585	0.3678	0.049*
C11	−0.0932 (2)	0.5116 (2)	0.1878 (2)	0.0487 (5)
H11A	−0.1347	0.5778	0.2144	0.058*
C12	−0.1158 (2)	0.4263 (2)	0.0587 (2)	0.0497 (5)
H12A	−0.1732	0.4336	−0.0035	0.060*
C13	−0.05201 (19)	0.3272 (2)	0.0198 (2)	0.0419 (5)
C14	−0.0662 (2)	0.2360 (2)	−0.1134 (2)	0.0544 (6)
H14A	−0.1214	0.2404	−0.1793	0.065*
C15	−0.0016 (2)	0.1441 (2)	−0.1458 (2)	0.0538 (6)
H15A	−0.0117	0.0873	−0.2335	0.065*
C16	0.0824 (2)	0.1320 (2)	−0.04811 (19)	0.0419 (5)
C17	0.1503 (2)	0.0364 (2)	−0.0762 (2)	0.0495 (5)
H17A	0.1435	−0.0225	−0.1624	0.059*
C18	0.2257 (2)	0.0301 (2)	0.0226 (2)	0.0481 (5)
H18A	0.2708	−0.0332	0.0050	0.058*
C19	0.23497 (19)	0.11972 (19)	0.1513 (2)	0.0404 (4)
H19A	0.2867	0.1140	0.2184	0.048*
C20	0.09807 (17)	0.21888 (18)	0.08438 (18)	0.0322 (4)
C21	0.03157 (17)	0.32046 (18)	0.11916 (18)	0.0328 (4)
C22	−0.0099 (3)	0.1695 (3)	0.4730 (3)	0.0630 (6)
H22A	−0.1049	0.1314	0.4615	0.095*
H22B	0.0331	0.2215	0.5646	0.095*
H22C	0.0276	0.0984	0.4346	0.095*

	U11	U22	U33	U12	U13	U23
Mn1	0.02964 (16)	0.03098 (16)	0.02770 (17)	0.01230 (12)	0.00583 (12)	0.00973 (13)
S1	0.0417 (3)	0.0368 (3)	0.0306 (3)	0.0196 (2)	0.0053 (2)	0.0085 (2)
O1	0.0404 (7)	0.0346 (7)	0.0434 (8)	0.0181 (6)	0.0034 (6)	0.0060 (6)
O2	0.0435 (8)	0.0426 (8)	0.0310 (7)	0.0208 (6)	0.0029 (6)	0.0030 (6)
O3	0.0562 (9)	0.0466 (9)	0.0550 (10)	0.0260 (8)	0.0250 (8)	0.0208 (8)
O4	0.0320 (7)	0.0576 (9)	0.0558 (10)	0.0166 (7)	0.0104 (7)	0.0320 (8)
O1W	0.0395 (8)	0.0434 (8)	0.0362 (8)	0.0050 (6)	0.0130 (6)	0.0109 (7)
Cl1	0.0447 (3)	0.0375 (3)	0.0495 (3)	0.0167 (2)	−0.0039 (2)	0.0159 (2)
N1	0.0453 (9)	0.0353 (8)	0.0324 (9)	0.0192 (7)	0.0084 (7)	0.0140 (7)
N2	0.0535 (10)	0.0471 (10)	0.0423 (10)	0.0269 (8)	0.0104 (8)	0.0212 (8)
N3	0.0470 (10)	0.0459 (10)	0.0438 (10)	0.0239 (8)	0.0125 (8)	0.0189 (8)
N4	0.0385 (8)	0.0383 (9)	0.0371 (9)	0.0172 (7)	0.0115 (7)	0.0152 (7)
N5	0.0294 (7)	0.0296 (8)	0.0324 (7)	0.0095 (6)	0.0048 (6)	0.0088 (6)
N6	0.0310 (7)	0.0340 (8)	0.0352 (9)	0.0120 (6)	0.0084 (6)	0.0158 (7)
C1	0.0378 (10)	0.0397 (10)	0.0308 (10)	0.0171 (8)	0.0039 (8)	0.0121 (8)
C2	0.0460 (11)	0.0391 (10)	0.0372 (11)	0.0127 (9)	0.0102 (9)	0.0198 (9)
C3	0.0520 (11)	0.0306 (9)	0.0347 (11)	0.0151 (8)	0.0080 (9)	0.0138 (8)
C4	0.0431 (10)	0.0341 (10)	0.0269 (9)	0.0162 (8)	0.0060 (8)	0.0112 (8)
C5	0.0470 (11)	0.0357 (10)	0.0350 (11)	0.0134 (8)	0.0100 (9)	0.0171 (9)
C6	0.0455 (11)	0.0297 (9)	0.0375 (11)	0.0151 (8)	0.0054 (9)	0.0132 (8)
C7	0.0333 (9)	0.0297 (9)	0.0310 (10)	0.0089 (7)	0.0077 (8)	0.0111 (8)
C8	0.0369 (10)	0.0389 (10)	0.0308 (10)	0.0178 (8)	0.0069 (8)	0.0088 (8)
C9	0.0290 (9)	0.0331 (10)	0.0315 (10)	0.0105 (7)	0.0088 (8)	0.0104 (8)
C10	0.0394 (10)	0.0386 (10)	0.0475 (12)	0.0165 (8)	0.0145 (9)	0.0202 (9)
C11	0.0410 (11)	0.0507 (12)	0.0704 (16)	0.0237 (10)	0.0162 (11)	0.0370 (12)
C12	0.0379 (11)	0.0564 (13)	0.0622 (15)	0.0126 (10)	0.0027 (10)	0.0382 (12)
C13	0.0335 (10)	0.0460 (11)	0.0443 (12)	0.0050 (8)	0.0006 (8)	0.0257 (10)
C14	0.0513 (13)	0.0608 (14)	0.0402 (13)	0.0046 (11)	−0.0061 (10)	0.0250 (11)
C15	0.0590 (13)	0.0531 (13)	0.0291 (11)	0.0032 (11)	0.0011 (10)	0.0109 (10)
C16	0.0390 (10)	0.0368 (10)	0.0334 (11)	0.0004 (8)	0.0062 (8)	0.0081 (9)
C17	0.0508 (12)	0.0381 (11)	0.0390 (12)	0.0061 (9)	0.0152 (10)	0.0021 (9)
C18	0.0422 (11)	0.0338 (11)	0.0557 (14)	0.0133 (9)	0.0162 (10)	0.0072 (10)
C19	0.0358 (10)	0.0341 (10)	0.0458 (12)	0.0132 (8)	0.0090 (9)	0.0125 (9)
C20	0.0271 (8)	0.0306 (9)	0.0318 (10)	0.0036 (7)	0.0057 (7)	0.0111 (8)
C21	0.0271 (8)	0.0348 (10)	0.0339 (10)	0.0050 (7)	0.0048 (7)	0.0168 (8)
C22	0.0745 (16)	0.0582 (15)	0.0655 (17)	0.0219 (13)	0.0239 (13)	0.0347 (12)

Mn1—O2	2.1128 (13)	C3—H3A	0.9300
Mn1—O1W	2.1937 (13)	C4—C5	1.379 (3)
Mn1—O4	2.2195 (14)	C5—C6	1.384 (3)
Mn1—N6	2.2659 (15)	C5—H5A	0.9300
Mn1—N5	2.3121 (15)	C6—H6A	0.9300
Mn1—Cl1	2.4725 (5)	C8—C9	1.523 (3)
S1—C7	1.7370 (18)	C8—H8A	0.9700
S1—C8	1.8129 (19)	C8—H8B	0.9700
O1—C9	1.242 (2)	C10—C11	1.395 (3)
O2—C9	1.252 (2)	C10—H10A	0.9300
O3—C1	1.357 (2)	C11—C12	1.360 (3)
O3—H3B	0.805 (16)	C11—H11A	0.9300
O4—C22	1.435 (3)	C12—C13	1.405 (3)
O4—H4B	0.797 (16)	C12—H12A	0.9300
O1W—H1WA	0.804 (15)	C13—C21	1.405 (3)
O1W—H1WB	0.815 (15)	C13—C14	1.429 (3)
N1—C7	1.343 (2)	C14—C15	1.343 (3)
N1—N2	1.359 (2)	C14—H14A	0.9300
N1—C4	1.438 (2)	C15—C16	1.427 (3)
N2—N3	1.284 (2)	C15—H15A	0.9300
N3—N4	1.366 (2)	C16—C17	1.404 (3)
N4—C7	1.322 (2)	C16—C20	1.406 (3)
N5—C19	1.325 (2)	C17—C18	1.353 (3)
N5—C20	1.353 (2)	C17—H17A	0.9300
N6—C10	1.326 (2)	C18—C19	1.395 (3)
N6—C21	1.353 (2)	C18—H18A	0.9300
C1—C6	1.386 (3)	C19—H19A	0.9300
C1—C2	1.390 (3)	C20—C21	1.447 (2)
C2—C3	1.373 (3)	C22—H22A	0.9600
C2—H2A	0.9300	C22—H22B	0.9600
C3—C4	1.387 (3)	C22—H22C	0.9600
O2—Mn1—O1W	86.83 (6)	N4—C7—N1	108.36 (16)
O2—Mn1—O4	96.20 (6)	N4—C7—S1	128.91 (15)
O1W—Mn1—O4	172.42 (6)	N1—C7—S1	122.72 (13)
O2—Mn1—N6	90.89 (5)	C9—C8—S1	108.62 (12)
O1W—Mn1—N6	87.38 (6)	C9—C8—H8A	110.0
O4—Mn1—N6	85.63 (5)	S1—C8—H8A	110.0
O2—Mn1—N5	161.07 (6)	C9—C8—H8B	110.0
O1W—Mn1—N5	83.48 (5)	S1—C8—H8B	110.0
O4—Mn1—N5	91.61 (6)	H8A—C8—H8B	108.3
N6—Mn1—N5	72.49 (5)	O1—C9—O2	125.37 (17)
O2—Mn1—Cl1	102.48 (4)	O1—C9—C8	118.10 (16)
O1W—Mn1—Cl1	93.64 (4)	O2—C9—C8	116.53 (15)
O4—Mn1—Cl1	92.49 (4)	N6—C10—C11	122.7 (2)
N6—Mn1—Cl1	166.62 (4)	N6—C10—H10A	118.6
N5—Mn1—Cl1	94.35 (4)	C11—C10—H10A	118.6
C7—S1—C8	99.25 (8)	C12—C11—C10	119.42 (19)
C9—O2—Mn1	148.24 (12)	C12—C11—H11A	120.3
C1—O3—H3B	106.1 (18)	C10—C11—H11A	120.3
C22—O4—Mn1	133.01 (14)	C11—C12—C13	119.71 (19)
C22—O4—H4B	114.4 (17)	C11—C12—H12A	120.1
Mn1—O4—H4B	112.6 (17)	C13—C12—H12A	120.1
Mn1—O1W—H1WA	118.9 (16)	C12—C13—C21	117.14 (19)
Mn1—O1W—H1WB	124.4 (16)	C12—C13—C14	123.71 (19)
H1WA—O1W—H1WB	108.7 (19)	C21—C13—C14	119.14 (19)
C7—N1—N2	108.33 (15)	C15—C14—C13	121.5 (2)
C7—N1—C4	128.64 (15)	C15—C14—H14A	119.3
N2—N1—C4	122.67 (15)	C13—C14—H14A	119.3
N3—N2—N1	106.35 (16)	C14—C15—C16	121.3 (2)
N2—N3—N4	111.19 (15)	C14—C15—H15A	119.4
C7—N4—N3	105.76 (15)	C16—C15—H15A	119.4
C19—N5—C20	117.63 (16)	C17—C16—C20	117.17 (19)
C19—N5—Mn1	126.95 (13)	C17—C16—C15	123.71 (19)
C20—N5—Mn1	115.21 (11)	C20—C16—C15	119.11 (19)
C10—N6—C21	118.22 (16)	C18—C17—C16	119.83 (19)
C10—N6—Mn1	125.14 (13)	C18—C17—H17A	120.1
C21—N6—Mn1	116.62 (11)	C16—C17—H17A	120.1
O3—C1—C6	123.01 (17)	C17—C18—C19	119.14 (19)
O3—C1—C2	117.16 (17)	C17—C18—H18A	120.4
C6—C1—C2	119.83 (17)	C19—C18—H18A	120.4
C3—C2—C1	119.98 (18)	N5—C19—C18	123.4 (2)
C3—C2—H2A	120.0	N5—C19—H19A	118.3
C1—C2—H2A	120.0	C18—C19—H19A	118.3
C2—C3—C4	119.58 (17)	N5—C20—C16	122.84 (17)
C2—C3—H3A	120.2	N5—C20—C21	117.54 (16)
C4—C3—H3A	120.2	C16—C20—C21	119.62 (17)
C5—C4—C3	121.15 (17)	N6—C21—C13	122.75 (17)
C5—C4—N1	120.23 (16)	N6—C21—C20	117.93 (16)
C3—C4—N1	118.59 (16)	C13—C21—C20	119.32 (17)
C4—C5—C6	118.93 (18)	O4—C22—H22A	109.5
C4—C5—H5A	120.5	O4—C22—H22B	109.5
C6—C5—H5A	120.5	H22A—C22—H22B	109.5
C5—C6—C1	120.40 (17)	O4—C22—H22C	109.5
C5—C6—H6A	119.8	H22A—C22—H22C	109.5
C1—C6—H6A	119.8	H22B—C22—H22C	109.5
O1W—Mn1—O2—C9	−77.1 (2)	N2—N1—C7—N4	−0.5 (2)
O4—Mn1—O2—C9	109.8 (2)	C4—N1—C7—N4	−173.59 (17)
N6—Mn1—O2—C9	−164.5 (2)	N2—N1—C7—S1	178.75 (13)
N5—Mn1—O2—C9	−136.3 (2)	C4—N1—C7—S1	5.7 (3)
Cl1—Mn1—O2—C9	15.9 (3)	C8—S1—C7—N4	18.08 (19)
O2—Mn1—O4—C22	−99.15 (19)	C8—S1—C7—N1	−161.03 (16)
N6—Mn1—O4—C22	170.4 (2)	C7—S1—C8—C9	166.78 (13)
N5—Mn1—O4—C22	98.12 (19)	Mn1—O2—C9—O1	177.25 (16)
Cl1—Mn1—O4—C22	3.69 (19)	Mn1—O2—C9—C8	−2.8 (3)
C7—N1—N2—N3	0.1 (2)	S1—C8—C9—O1	14.7 (2)
C4—N1—N2—N3	173.67 (17)	S1—C8—C9—O2	−165.34 (14)
N1—N2—N3—N4	0.4 (2)	C21—N6—C10—C11	0.9 (3)
N2—N3—N4—C7	−0.7 (2)	Mn1—N6—C10—C11	179.25 (14)
O2—Mn1—N5—C19	149.03 (17)	N6—C10—C11—C12	−0.7 (3)
O1W—Mn1—N5—C19	89.35 (15)	C10—C11—C12—C13	−0.3 (3)
O4—Mn1—N5—C19	−96.44 (15)	C11—C12—C13—C21	1.0 (3)
N6—Mn1—N5—C19	178.65 (16)	C11—C12—C13—C14	−177.97 (19)
Cl1—Mn1—N5—C19	−3.82 (15)	C12—C13—C14—C15	179.1 (2)
O2—Mn1—N5—C20	−25.6 (2)	C21—C13—C14—C15	0.1 (3)
O1W—Mn1—N5—C20	−85.32 (12)	C13—C14—C15—C16	1.1 (3)
O4—Mn1—N5—C20	88.88 (12)	C14—C15—C16—C17	178.9 (2)
N6—Mn1—N5—C20	3.98 (11)	C14—C15—C16—C20	−0.4 (3)
Cl1—Mn1—N5—C20	−178.50 (11)	C20—C16—C17—C18	0.7 (3)
O2—Mn1—N6—C10	−10.40 (15)	C15—C16—C17—C18	−178.6 (2)
O1W—Mn1—N6—C10	−97.18 (15)	C16—C17—C18—C19	−0.3 (3)
O4—Mn1—N6—C10	85.75 (15)	C20—N5—C19—C18	0.5 (3)
N5—Mn1—N6—C10	178.83 (16)	Mn1—N5—C19—C18	−174.03 (14)
Cl1—Mn1—N6—C10	168.12 (13)	C17—C18—C19—N5	−0.4 (3)
O2—Mn1—N6—C21	167.97 (12)	C19—N5—C20—C16	−0.1 (3)
O1W—Mn1—N6—C21	81.19 (12)	Mn1—N5—C20—C16	175.10 (13)
O4—Mn1—N6—C21	−95.88 (12)	C19—N5—C20—C21	−179.93 (15)
N5—Mn1—N6—C21	−2.80 (11)	Mn1—N5—C20—C21	−4.72 (19)
Cl1—Mn1—N6—C21	−13.5 (3)	C17—C16—C20—N5	−0.5 (3)
O3—C1—C2—C3	175.91 (18)	C15—C16—C20—N5	178.84 (17)
C6—C1—C2—C3	−3.7 (3)	C17—C16—C20—C21	179.34 (17)
C1—C2—C3—C4	1.4 (3)	C15—C16—C20—C21	−1.3 (3)
C2—C3—C4—C5	1.8 (3)	C10—N6—C21—C13	−0.1 (3)
C2—C3—C4—N1	−176.58 (17)	Mn1—N6—C21—C13	−178.56 (13)
C7—N1—C4—C5	−65.4 (3)	C10—N6—C21—C20	179.92 (15)
N2—N1—C4—C5	122.4 (2)	Mn1—N6—C21—C20	1.4 (2)
C7—N1—C4—C3	113.0 (2)	C12—C13—C21—N6	−0.9 (3)
N2—N1—C4—C3	−59.2 (3)	C14—C13—C21—N6	178.17 (17)
C3—C4—C5—C6	−2.6 (3)	C12—C13—C21—C20	179.12 (16)
N1—C4—C5—C6	175.72 (17)	C14—C13—C21—C20	−1.8 (3)
C4—C5—C6—C1	0.3 (3)	N5—C20—C21—N6	2.3 (2)
O3—C1—C6—C5	−176.73 (18)	C16—C20—C21—N6	−177.54 (16)
C2—C1—C6—C5	2.9 (3)	N5—C20—C21—C13	−177.72 (15)
N3—N4—C7—N1	0.7 (2)	C16—C20—C21—C13	2.5 (2)
N3—N4—C7—S1	−178.50 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···Cl1i	0.805 (16)	2.334 (17)	3.1344 (16)	173 (2)
O4—H4B···O1ii	0.797 (16)	1.889 (17)	2.6788 (18)	171 (2)
O1W—H1WA···N4iii	0.804 (15)	2.006 (15)	2.808 (2)	175 (2)
O1W—H1WB···Cl1iii	0.815 (15)	2.376 (17)	3.1665 (15)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯Cl1i	0.805 (16)	2.334 (17)	3.1344 (16)	173 (2)
O4—H4B⋯O1ii	0.797 (16)	1.889 (17)	2.6788 (18)	171 (2)
O1W—H1WA⋯N4iii	0.804 (15)	2.006 (15)	2.808 (2)	175 (2)
O1W—H1WB⋯Cl1iii	0.815 (15)	2.376 (17)	3.1665 (15)	164 (2)

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