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Acta Cryst. (2008). E64, m1609    [ doi:10.1107/S1600536808038245 ]

Aquachlorido{1-[1-(4-hydroxyphenyl)-1H-tetrazol-5-ylsulfanyl]acetato}(methanol)(1,10-phenanthroline)manganese(II)

J.-L. Yin and Y.-L. Feng

Abstract top

The title complex, [Mn(C9H7N4O3S)Cl(C12H8N2)(CH4O)(H2O)], contains an MnII ion six-coordinated by one O atom from the 2-[1-(4-hydroxyphenyl)-1H-tetrazol-5-ylsulfanyl]acetate ligand, two N atoms from a chelating 1,10-phenanthroline ligand, one O atom from a methanol molecule, one Cl atom and one water molecule in a distorted octahedral coordination geometry. The existence of O-H...Cl, O-H...N and O-H...O hydrogen bonds further produces a two-dimensional structure.

Comment top

Recently much interest has been focused on the design and synthesis of complexes based on rigid aromatic carboxylic acids (Hu et al., 2006; Zhang et al., 2006). However, the coordination chemistry and structural properties of complexes based on flexible heterocyclic acetate ligand have been rarely documented to date. 1-(4-hydroxyphenyl)-5-thioacetatetetrazole possesses one phenolic hydroxy group and one flexible thioacetate group, which has senven potential coordinated sites. As illustrated in Fig. 1, MnII ion is in a distorted octahedral coordination environment, coordinated by one O atom of 1-(4-hydroxyphenyl)-5-thioacetatetetrazole ligand, two N atoms from phen, one O atom from methanol molecule, one Cl atom and one water molecule.

The existence of O—H···Cl, O—H···N, and O—H···O three types of hydrogen bonds further produce two-dimensional structure.

Related literature top

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

Experimental top

Manganese chloride tetrahydrate 0.5 mmol (0.099 g), 1-(4-hydroxyphenyl)-5-thioacetatetetrazole 0.5 mmol (0.061 g), 1,10-phenanthroline 0.25 mmol (0.050 g), were mixed in 16 ml of 15:1 distilled water/methanol, and stirred for 2 h under 333 K. Then the reaction mixture was filtered and well shaped colourless crystals of the title compound, Mn(H2O)Cl(MeOH)(phen)(C9H7N4O3S), was obtained from the mother liquor by slow evaporation at room temperature for several days.

Refinement top

The H atoms bonded to C atoms were positioned geometrically [aromatic C—H = 0.93 Å, aliphatic C—H = 0.97 Å, Uiso(H) = 1.2Ueq(C)], and methyl group C—H = 0.96 Å, Uiso(H) = 1.5Ueq(C). The H atoms bonded to O atoms were located in a difference Fourier maps and refined with O—H distance restraints of 0.82 and Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are shown at the 30% probability level.
Aquachlorido{1-[1-(4-hydroxyphenyl)-1H-tetrazol-5- ylsulfanyl]acetato}(methanol)(1,10-phenanthroline)manganese(II) top
Crystal data top
[Mn(C9H7N4O3S)Cl(C12H8N2)(CH4O)(H2O)]Z = 2
Mr = 571.90F(000) = 586
Triclinic, P1Dx = 1.576 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5565 (3) ÅCell parameters from 5369 reflections
b = 11.4969 (2) Åθ = 2.0–25.0°
c = 11.5931 (2) ŵ = 0.79 mm−1
α = 114.362 (1)°T = 296 K
β = 96.841 (1)°Block, colourless
γ = 103.969 (1)°0.34 × 0.23 × 0.11 mm
V = 1205.17 (5) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		4186 independent reflections
Radiation source: fine-focus sealed tube3802 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.806, Tmax = 0.916k = −13→13
13742 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2751P]
where P = (Fo2 + 2Fc2)/3
4186 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.33 e Å−3
8 restraintsΔρmin = −0.27 e Å−3
Crystal data top
[Mn(C9H7N4O3S)Cl(C12H8N2)(CH4O)(H2O)]γ = 103.969 (1)°
Mr = 571.90V = 1205.17 (5) Å3
Triclinic, P1Z = 2
a = 10.5565 (3) ÅMo Kα radiation
b = 11.4969 (2) ŵ = 0.79 mm−1
c = 11.5931 (2) ÅT = 296 K
α = 114.362 (1)°0.34 × 0.23 × 0.11 mm
β = 96.841 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		4186 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3802 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 0.916Rint = 0.019
13742 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081Δρmax = 0.33 e Å−3
S = 1.07Δρmin = −0.27 e Å−3
4186 reflectionsAbsolute structure: ?
337 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.19580 (2)0.37914 (3)0.39006 (2)0.03039 (10)
S10.41984 (5)0.76432 (5)0.90045 (5)0.03782 (13)
O10.22915 (13)0.76112 (13)0.71081 (14)0.0432 (3)
O20.20363 (13)0.56470 (13)0.54313 (13)0.0433 (3)
O30.30543 (16)1.00580 (15)1.46112 (16)0.0506 (4)
H3B0.322 (3)1.0813 (18)1.469 (3)0.061*
O40.01155 (13)0.25511 (15)0.41066 (15)0.0459 (3)
H4B−0.0559 (19)0.259 (2)0.375 (2)0.055*
O1W0.36180 (14)0.49567 (15)0.34462 (15)0.0436 (3)
H1WA0.378 (2)0.461 (2)0.2748 (16)0.052*
H1WB0.4312 (19)0.551 (2)0.3980 (18)0.052*
Cl10.34450 (5)0.30009 (5)0.50090 (5)0.04618 (14)
N10.55547 (16)0.73208 (15)1.09287 (15)0.0371 (4)
N20.63935 (18)0.66518 (18)1.11195 (17)0.0454 (4)
N30.65952 (17)0.59784 (17)0.99986 (17)0.0443 (4)
N40.59187 (15)0.61830 (16)0.90566 (16)0.0376 (4)
N50.17387 (14)0.21255 (14)0.18296 (15)0.0327 (3)
N60.05314 (15)0.40551 (15)0.24743 (15)0.0331 (3)
C10.37482 (19)0.94561 (19)1.37606 (18)0.0371 (4)
C20.3594 (2)0.8111 (2)1.34184 (19)0.0401 (4)
H2A0.30790.76791.38110.048*
C30.4201 (2)0.74207 (19)1.25000 (19)0.0394 (4)
H3A0.40830.65151.22550.047*
C40.49903 (19)0.80822 (18)1.19405 (18)0.0352 (4)
C50.5208 (2)0.94331 (19)1.23160 (19)0.0389 (4)
H5A0.57680.98771.19610.047*
C60.45784 (19)1.01185 (19)1.32297 (19)0.0382 (4)
H6A0.47141.10291.34890.046*
C70.52702 (18)0.70145 (17)0.96571 (18)0.0326 (4)
C80.38078 (19)0.64340 (19)0.72948 (18)0.0371 (4)
H8A0.45810.65970.69400.045*
H8B0.35870.55260.72040.045*
C90.26138 (17)0.65837 (18)0.65563 (18)0.0325 (4)
C10−0.00740 (19)0.4990 (2)0.2799 (2)0.0405 (4)
H10A0.00800.55850.36780.049*
C11−0.0932 (2)0.5116 (2)0.1878 (2)0.0487 (5)
H11A−0.13470.57780.21440.058*
C12−0.1158 (2)0.4263 (2)0.0587 (2)0.0497 (5)
H12A−0.17320.4336−0.00350.060*
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−0.12140.2404−0.17930.065*
C15−0.0016 (2)0.1441 (2)−0.1458 (2)0.0538 (6)
H15A−0.01170.0873−0.23350.065*
C160.0824 (2)0.1320 (2)−0.04811 (19)0.0419 (5)
C170.1503 (2)0.0364 (2)−0.0762 (2)0.0495 (5)
H17A0.1435−0.0225−0.16240.059*
C180.2257 (2)0.0301 (2)0.0226 (2)0.0481 (5)
H18A0.2708−0.03320.00500.058*
C190.23497 (19)0.11972 (19)0.1513 (2)0.0404 (4)
H19A0.28670.11400.21840.048*
C200.09807 (17)0.21888 (18)0.08438 (18)0.0322 (4)
C210.03157 (17)0.32046 (18)0.11916 (18)0.0328 (4)
C22−0.0099 (3)0.1695 (3)0.4730 (3)0.0630 (6)
H22A−0.10490.13140.46150.095*
H22B0.03310.22150.56460.095*
H22C0.02760.09840.43460.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02964 (16)0.03098 (16)0.02770 (17)0.01230 (12)0.00583 (12)0.00973 (13)
S10.0417 (3)0.0368 (3)0.0306 (3)0.0196 (2)0.0053 (2)0.0085 (2)
O10.0404 (7)0.0346 (7)0.0434 (8)0.0181 (6)0.0034 (6)0.0060 (6)
O20.0435 (8)0.0426 (8)0.0310 (7)0.0208 (6)0.0029 (6)0.0030 (6)
O30.0562 (9)0.0466 (9)0.0550 (10)0.0260 (8)0.0250 (8)0.0208 (8)
O40.0320 (7)0.0576 (9)0.0558 (10)0.0166 (7)0.0104 (7)0.0320 (8)
O1W0.0395 (8)0.0434 (8)0.0362 (8)0.0050 (6)0.0130 (6)0.0109 (7)
Cl10.0447 (3)0.0375 (3)0.0495 (3)0.0167 (2)−0.0039 (2)0.0159 (2)
N10.0453 (9)0.0353 (8)0.0324 (9)0.0192 (7)0.0084 (7)0.0140 (7)
N20.0535 (10)0.0471 (10)0.0423 (10)0.0269 (8)0.0104 (8)0.0212 (8)
N30.0470 (10)0.0459 (10)0.0438 (10)0.0239 (8)0.0125 (8)0.0189 (8)
N40.0385 (8)0.0383 (9)0.0371 (9)0.0172 (7)0.0115 (7)0.0152 (7)
N50.0294 (7)0.0296 (8)0.0324 (7)0.0095 (6)0.0048 (6)0.0088 (6)
N60.0310 (7)0.0340 (8)0.0352 (9)0.0120 (6)0.0084 (6)0.0158 (7)
C10.0378 (10)0.0397 (10)0.0308 (10)0.0171 (8)0.0039 (8)0.0121 (8)
C20.0460 (11)0.0391 (10)0.0372 (11)0.0127 (9)0.0102 (9)0.0198 (9)
C30.0520 (11)0.0306 (9)0.0347 (11)0.0151 (8)0.0080 (9)0.0138 (8)
C40.0431 (10)0.0341 (10)0.0269 (9)0.0162 (8)0.0060 (8)0.0112 (8)
C50.0470 (11)0.0357 (10)0.0350 (11)0.0134 (8)0.0100 (9)0.0171 (9)
C60.0455 (11)0.0297 (9)0.0375 (11)0.0151 (8)0.0054 (9)0.0132 (8)
C70.0333 (9)0.0297 (9)0.0310 (10)0.0089 (7)0.0077 (8)0.0111 (8)
C80.0369 (10)0.0389 (10)0.0308 (10)0.0178 (8)0.0069 (8)0.0088 (8)
C90.0290 (9)0.0331 (10)0.0315 (10)0.0105 (7)0.0088 (8)0.0104 (8)
C100.0394 (10)0.0386 (10)0.0475 (12)0.0165 (8)0.0145 (9)0.0202 (9)
C110.0410 (11)0.0507 (12)0.0704 (16)0.0237 (10)0.0162 (11)0.0370 (12)
C120.0379 (11)0.0564 (13)0.0622 (15)0.0126 (10)0.0027 (10)0.0382 (12)
C130.0335 (10)0.0460 (11)0.0443 (12)0.0050 (8)0.0006 (8)0.0257 (10)
C140.0513 (13)0.0608 (14)0.0402 (13)0.0046 (11)−0.0061 (10)0.0250 (11)
C150.0590 (13)0.0531 (13)0.0291 (11)0.0032 (11)0.0011 (10)0.0109 (10)
C160.0390 (10)0.0368 (10)0.0334 (11)0.0004 (8)0.0062 (8)0.0081 (9)
C170.0508 (12)0.0381 (11)0.0390 (12)0.0061 (9)0.0152 (10)0.0021 (9)
C180.0422 (11)0.0338 (11)0.0557 (14)0.0133 (9)0.0162 (10)0.0072 (10)
C190.0358 (10)0.0341 (10)0.0458 (12)0.0132 (8)0.0090 (9)0.0125 (9)
C200.0271 (8)0.0306 (9)0.0318 (10)0.0036 (7)0.0057 (7)0.0111 (8)
C210.0271 (8)0.0348 (10)0.0339 (10)0.0050 (7)0.0048 (7)0.0168 (8)
C220.0745 (16)0.0582 (15)0.0655 (17)0.0219 (13)0.0239 (13)0.0347 (12)
Geometric parameters (Å, °) top
Mn1—O22.1128 (13)C3—H3A0.9300
Mn1—O1W2.1937 (13)C4—C51.379 (3)
Mn1—O42.2195 (14)C5—C61.384 (3)
Mn1—N62.2659 (15)C5—H5A0.9300
Mn1—N52.3121 (15)C6—H6A0.9300
Mn1—Cl12.4725 (5)C8—C91.523 (3)
S1—C71.7370 (18)C8—H8A0.9700
S1—C81.8129 (19)C8—H8B0.9700
O1—C91.242 (2)C10—C111.395 (3)
O2—C91.252 (2)C10—H10A0.9300
O3—C11.357 (2)C11—C121.360 (3)
O3—H3B0.805 (16)C11—H11A0.9300
O4—C221.435 (3)C12—C131.405 (3)
O4—H4B0.797 (16)C12—H12A0.9300
O1W—H1WA0.804 (15)C13—C211.405 (3)
O1W—H1WB0.815 (15)C13—C141.429 (3)
N1—C71.343 (2)C14—C151.343 (3)
N1—N21.359 (2)C14—H14A0.9300
N1—C41.438 (2)C15—C161.427 (3)
N2—N31.284 (2)C15—H15A0.9300
N3—N41.366 (2)C16—C171.404 (3)
N4—C71.322 (2)C16—C201.406 (3)
N5—C191.325 (2)C17—C181.353 (3)
N5—C201.353 (2)C17—H17A0.9300
N6—C101.326 (2)C18—C191.395 (3)
N6—C211.353 (2)C18—H18A0.9300
C1—C61.386 (3)C19—H19A0.9300
C1—C21.390 (3)C20—C211.447 (2)
C2—C31.373 (3)C22—H22A0.9600
C2—H2A0.9300C22—H22B0.9600
C3—C41.387 (3)C22—H22C0.9600
O2—Mn1—O1W86.83 (6)N4—C7—N1108.36 (16)
O2—Mn1—O496.20 (6)N4—C7—S1128.91 (15)
O1W—Mn1—O4172.42 (6)N1—C7—S1122.72 (13)
O2—Mn1—N690.89 (5)C9—C8—S1108.62 (12)
O1W—Mn1—N687.38 (6)C9—C8—H8A110.0
O4—Mn1—N685.63 (5)S1—C8—H8A110.0
O2—Mn1—N5161.07 (6)C9—C8—H8B110.0
O1W—Mn1—N583.48 (5)S1—C8—H8B110.0
O4—Mn1—N591.61 (6)H8A—C8—H8B108.3
N6—Mn1—N572.49 (5)O1—C9—O2125.37 (17)
O2—Mn1—Cl1102.48 (4)O1—C9—C8118.10 (16)
O1W—Mn1—Cl193.64 (4)O2—C9—C8116.53 (15)
O4—Mn1—Cl192.49 (4)N6—C10—C11122.7 (2)
N6—Mn1—Cl1166.62 (4)N6—C10—H10A118.6
N5—Mn1—Cl194.35 (4)C11—C10—H10A118.6
C7—S1—C899.25 (8)C12—C11—C10119.42 (19)
C9—O2—Mn1148.24 (12)C12—C11—H11A120.3
C1—O3—H3B106.1 (18)C10—C11—H11A120.3
C22—O4—Mn1133.01 (14)C11—C12—C13119.71 (19)
C22—O4—H4B114.4 (17)C11—C12—H12A120.1
Mn1—O4—H4B112.6 (17)C13—C12—H12A120.1
Mn1—O1W—H1WA118.9 (16)C12—C13—C21117.14 (19)
Mn1—O1W—H1WB124.4 (16)C12—C13—C14123.71 (19)
H1WA—O1W—H1WB108.7 (19)C21—C13—C14119.14 (19)
C7—N1—N2108.33 (15)C15—C14—C13121.5 (2)
C7—N1—C4128.64 (15)C15—C14—H14A119.3
N2—N1—C4122.67 (15)C13—C14—H14A119.3
N3—N2—N1106.35 (16)C14—C15—C16121.3 (2)
N2—N3—N4111.19 (15)C14—C15—H15A119.4
C7—N4—N3105.76 (15)C16—C15—H15A119.4
C19—N5—C20117.63 (16)C17—C16—C20117.17 (19)
C19—N5—Mn1126.95 (13)C17—C16—C15123.71 (19)
C20—N5—Mn1115.21 (11)C20—C16—C15119.11 (19)
C10—N6—C21118.22 (16)C18—C17—C16119.83 (19)
C10—N6—Mn1125.14 (13)C18—C17—H17A120.1
C21—N6—Mn1116.62 (11)C16—C17—H17A120.1
O3—C1—C6123.01 (17)C17—C18—C19119.14 (19)
O3—C1—C2117.16 (17)C17—C18—H18A120.4
C6—C1—C2119.83 (17)C19—C18—H18A120.4
C3—C2—C1119.98 (18)N5—C19—C18123.4 (2)
C3—C2—H2A120.0N5—C19—H19A118.3
C1—C2—H2A120.0C18—C19—H19A118.3
C2—C3—C4119.58 (17)N5—C20—C16122.84 (17)
C2—C3—H3A120.2N5—C20—C21117.54 (16)
C4—C3—H3A120.2C16—C20—C21119.62 (17)
C5—C4—C3121.15 (17)N6—C21—C13122.75 (17)
C5—C4—N1120.23 (16)N6—C21—C20117.93 (16)
C3—C4—N1118.59 (16)C13—C21—C20119.32 (17)
C4—C5—C6118.93 (18)O4—C22—H22A109.5
C4—C5—H5A120.5O4—C22—H22B109.5
C6—C5—H5A120.5H22A—C22—H22B109.5
C5—C6—C1120.40 (17)O4—C22—H22C109.5
C5—C6—H6A119.8H22A—C22—H22C109.5
C1—C6—H6A119.8H22B—C22—H22C109.5
O1W—Mn1—O2—C9−77.1 (2)N2—N1—C7—N4−0.5 (2)
O4—Mn1—O2—C9109.8 (2)C4—N1—C7—N4−173.59 (17)
N6—Mn1—O2—C9−164.5 (2)N2—N1—C7—S1178.75 (13)
N5—Mn1—O2—C9−136.3 (2)C4—N1—C7—S15.7 (3)
Cl1—Mn1—O2—C915.9 (3)C8—S1—C7—N418.08 (19)
O2—Mn1—O4—C22−99.15 (19)C8—S1—C7—N1−161.03 (16)
N6—Mn1—O4—C22170.4 (2)C7—S1—C8—C9166.78 (13)
N5—Mn1—O4—C2298.12 (19)Mn1—O2—C9—O1177.25 (16)
Cl1—Mn1—O4—C223.69 (19)Mn1—O2—C9—C8−2.8 (3)
C7—N1—N2—N30.1 (2)S1—C8—C9—O114.7 (2)
C4—N1—N2—N3173.67 (17)S1—C8—C9—O2−165.34 (14)
N1—N2—N3—N40.4 (2)C21—N6—C10—C110.9 (3)
N2—N3—N4—C7−0.7 (2)Mn1—N6—C10—C11179.25 (14)
O2—Mn1—N5—C19149.03 (17)N6—C10—C11—C12−0.7 (3)
O1W—Mn1—N5—C1989.35 (15)C10—C11—C12—C13−0.3 (3)
O4—Mn1—N5—C19−96.44 (15)C11—C12—C13—C211.0 (3)
N6—Mn1—N5—C19178.65 (16)C11—C12—C13—C14−177.97 (19)
Cl1—Mn1—N5—C19−3.82 (15)C12—C13—C14—C15179.1 (2)
O2—Mn1—N5—C20−25.6 (2)C21—C13—C14—C150.1 (3)
O1W—Mn1—N5—C20−85.32 (12)C13—C14—C15—C161.1 (3)
O4—Mn1—N5—C2088.88 (12)C14—C15—C16—C17178.9 (2)
N6—Mn1—N5—C203.98 (11)C14—C15—C16—C20−0.4 (3)
Cl1—Mn1—N5—C20−178.50 (11)C20—C16—C17—C180.7 (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—C1085.75 (15)C20—N5—C19—C180.5 (3)
N5—Mn1—N6—C10178.83 (16)Mn1—N5—C19—C18−174.03 (14)
Cl1—Mn1—N6—C10168.12 (13)C17—C18—C19—N5−0.4 (3)
O2—Mn1—N6—C21167.97 (12)C19—N5—C20—C16−0.1 (3)
O1W—Mn1—N6—C2181.19 (12)Mn1—N5—C20—C16175.10 (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—C3175.91 (18)C15—C16—C20—N5178.84 (17)
C6—C1—C2—C3−3.7 (3)C17—C16—C20—C21179.34 (17)
C1—C2—C3—C41.4 (3)C15—C16—C20—C21−1.3 (3)
C2—C3—C4—C51.8 (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—C20179.92 (15)
N2—N1—C4—C5122.4 (2)Mn1—N6—C21—C201.4 (2)
C7—N1—C4—C3113.0 (2)C12—C13—C21—N6−0.9 (3)
N2—N1—C4—C3−59.2 (3)C14—C13—C21—N6178.17 (17)
C3—C4—C5—C6−2.6 (3)C12—C13—C21—C20179.12 (16)
N1—C4—C5—C6175.72 (17)C14—C13—C21—C20−1.8 (3)
C4—C5—C6—C10.3 (3)N5—C20—C21—N62.3 (2)
O3—C1—C6—C5−176.73 (18)C16—C20—C21—N6−177.54 (16)
C2—C1—C6—C52.9 (3)N5—C20—C21—C13−177.72 (15)
N3—N4—C7—N10.7 (2)C16—C20—C21—C132.5 (2)
N3—N4—C7—S1−178.50 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···Cl1i0.81 (2)2.33 (2)3.1344 (16)173 (2)
O4—H4B···O1ii0.80 (2)1.89 (2)2.6788 (18)171 (2)
O1W—H1WA···N4iii0.80 (2)2.01 (2)2.808 (2)175 (2)
O1W—H1WB···Cl1iii0.82 (2)2.38 (2)3.1665 (15)164 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···Cl1i0.81 (2)2.33 (2)3.1344 (16)173 (2)
O4—H4B···O1ii0.80 (2)1.89 (2)2.6788 (18)171 (2)
O1W—H1WA···N4iii0.80 (2)2.01 (2)2.808 (2)175 (2)
O1W—H1WB···Cl1iii0.82 (2)2.38 (2)3.1665 (15)164 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.
references
References top

Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Hu, T. L., Li, J. R., Liu, C. S., Shi, X. S., Zhou, J. N., Bu, X. H. & Ribas, J. (2006). Inorg. Chem. 45, 162–173.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Zhang, L. Y., Zhang, J. P., Lin, Y. Y. & Chen, X. M. (2006). Cryst. Growth Des. 7, 1684–1689.