In the title compound, [MnCl2(C6H6N4S2)2]·CH3OH, the MnII ion is coordinated by two 2,2'-diamino-4,4'-bithiazole ligands and two Cl- anions in cis positions to form a distorted octahedral coordination geometry. In the crystal structure, a three-dimensional supramolecular structure involving hydrogen bonding and aromatic packing is observed.
Supporting information
CCDC reference: 610856
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.057
- wR factor = 0.136
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for S2 - C5 .. 7.23 su
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C2 .. 5.16 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - Cl1 .. 5.51 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S3 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S4 in Main Residue . ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. S2 .. 3.34 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).
cis-Dichlorobis(2,2'-diamino-4,4'-bi-1,3-thiazole)manganese(II) methanol
solvate
top
Crystal data top
[MnCl2(C6H6N4S2)2]·CH4O | F(000) = 1124 |
Mr = 554.42 | Dx = 1.672 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4763 reflections |
a = 11.451 (2) Å | θ = 2.4–27.8° |
b = 13.614 (3) Å | µ = 1.24 mm−1 |
c = 14.892 (3) Å | T = 296 K |
β = 108.39 (3)° | Prism, yellow |
V = 2203.0 (9) Å3 | 0.26 × 0.10 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 3992 independent reflections |
Radiation source: fine-focus sealed tube | 3543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.738, Tmax = 0.907 | k = −15→16 |
16004 measured reflections | l = −17→17 |
Refinement top
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0542P)2 + 3.4155P] where P = (Fo2 + 2Fc2)/3 |
3992 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Mn1 | 0.21349 (5) | 0.15786 (4) | 0.29063 (4) | 0.03584 (19) | |
Cl1 | 0.06956 (10) | 0.19672 (8) | 0.38513 (8) | 0.0489 (3) | |
Cl2 | 0.38139 (10) | 0.26968 (8) | 0.38847 (8) | 0.0478 (3) | |
N1 | 0.3358 (3) | 0.0958 (3) | 0.2115 (3) | 0.0458 (9) | |
N2 | 0.3005 (3) | 0.0227 (2) | 0.3706 (3) | 0.0437 (9) | |
N3 | 0.3183 (4) | 0.2065 (4) | 0.0872 (3) | 0.0698 (13) | |
H3A | 0.2779 | 0.2485 | 0.1090 | 0.084* | |
H3B | 0.3347 | 0.2187 | 0.0359 | 0.084* | |
N4 | 0.2464 (4) | 0.0247 (3) | 0.5094 (3) | 0.0622 (11) | |
H4A | 0.2000 | 0.0753 | 0.4912 | 0.075* | |
H4B | 0.2539 | −0.0017 | 0.5634 | 0.075* | |
N5 | 0.0548 (3) | 0.0761 (2) | 0.1757 (2) | 0.0404 (8) | |
N6 | 0.1158 (3) | 0.2732 (2) | 0.1851 (2) | 0.0403 (8) | |
N7 | 0.0826 (4) | −0.0939 (3) | 0.1972 (3) | 0.0617 (11) | |
H7A | 0.1515 | −0.0868 | 0.2416 | 0.074* | |
H7B | 0.0542 | −0.1517 | 0.1801 | 0.074* | |
N8 | 0.2297 (4) | 0.4181 (3) | 0.2337 (3) | 0.0651 (12) | |
H8A | 0.2911 | 0.3872 | 0.2716 | 0.078* | |
H8B | 0.2323 | 0.4809 | 0.2285 | 0.078* | |
S1 | 0.43960 (14) | 0.03567 (15) | 0.09235 (12) | 0.0857 (6) | |
S2 | 0.40131 (12) | −0.11306 (10) | 0.49067 (12) | 0.0708 (5) | |
S3 | −0.11698 (13) | −0.02778 (11) | 0.06307 (11) | 0.0709 (4) | |
S4 | 0.00675 (12) | 0.42925 (9) | 0.10428 (10) | 0.0589 (4) | |
C1 | 0.3559 (4) | 0.1210 (4) | 0.1340 (4) | 0.0547 (12) | |
C2 | 0.4469 (5) | −0.0373 (5) | 0.1888 (5) | 0.0768 (17) | |
H2 | 0.4861 | −0.0980 | 0.2007 | 0.092* | |
C3 | 0.3888 (4) | 0.0047 (4) | 0.2442 (4) | 0.0547 (13) | |
C4 | 0.3053 (4) | −0.0120 (3) | 0.4552 (4) | 0.0485 (11) | |
C5 | 0.4368 (4) | −0.1079 (4) | 0.3902 (5) | 0.0714 (18) | |
H5 | 0.4894 | −0.1517 | 0.3743 | 0.086* | |
C6 | 0.3782 (4) | −0.0300 (3) | 0.3333 (4) | 0.0525 (12) | |
C7 | 0.0197 (4) | −0.0149 (3) | 0.1550 (3) | 0.0472 (11) | |
C8 | −0.1251 (5) | 0.0975 (4) | 0.0513 (4) | 0.0683 (15) | |
H8 | −0.1882 | 0.1312 | 0.0071 | 0.082* | |
C9 | −0.0272 (4) | 0.1405 (3) | 0.1150 (3) | 0.0466 (11) | |
C10 | 0.1302 (4) | 0.3685 (3) | 0.1830 (3) | 0.0453 (10) | |
C11 | −0.0671 (4) | 0.3184 (4) | 0.0748 (4) | 0.0551 (12) | |
H11 | −0.1448 | 0.3105 | 0.0308 | 0.066* | |
C12 | 0.0018 (4) | 0.2448 (3) | 0.1234 (3) | 0.0454 (10) | |
C13 | 0.2887 (8) | 0.6906 (6) | 0.2152 (7) | 0.130 (4) | |
H13A | 0.2738 | 0.7517 | 0.1813 | 0.194* | |
H13B | 0.3718 | 0.6698 | 0.2243 | 0.194* | |
H13C | 0.2766 | 0.6991 | 0.2756 | 0.194* | |
O1 | 0.2069 (4) | 0.6192 (3) | 0.1631 (3) | 0.0806 (12) | |
H1 | 0.1360 | 0.6377 | 0.1539 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0335 (3) | 0.0301 (3) | 0.0417 (4) | 0.0049 (2) | 0.0087 (3) | 0.0020 (3) |
Cl1 | 0.0507 (6) | 0.0415 (6) | 0.0596 (7) | 0.0067 (5) | 0.0245 (5) | 0.0066 (5) |
Cl2 | 0.0425 (6) | 0.0424 (6) | 0.0524 (6) | −0.0032 (5) | 0.0064 (5) | 0.0020 (5) |
N1 | 0.0384 (19) | 0.051 (2) | 0.049 (2) | −0.0009 (17) | 0.0159 (17) | −0.0123 (17) |
N2 | 0.0319 (18) | 0.0335 (19) | 0.059 (2) | 0.0020 (15) | 0.0043 (16) | 0.0022 (17) |
N3 | 0.073 (3) | 0.092 (4) | 0.054 (3) | −0.007 (3) | 0.034 (2) | −0.007 (3) |
N4 | 0.054 (2) | 0.067 (3) | 0.060 (3) | 0.007 (2) | 0.012 (2) | 0.022 (2) |
N5 | 0.0374 (18) | 0.0367 (19) | 0.044 (2) | −0.0009 (15) | 0.0088 (16) | −0.0045 (15) |
N6 | 0.0389 (19) | 0.0345 (19) | 0.044 (2) | 0.0040 (15) | 0.0088 (16) | 0.0053 (15) |
N7 | 0.061 (3) | 0.035 (2) | 0.077 (3) | −0.0085 (19) | 0.005 (2) | −0.008 (2) |
N8 | 0.060 (3) | 0.040 (2) | 0.079 (3) | −0.001 (2) | −0.002 (2) | 0.011 (2) |
S1 | 0.0613 (9) | 0.1192 (14) | 0.0860 (11) | 0.0032 (9) | 0.0368 (8) | −0.0425 (10) |
S2 | 0.0480 (7) | 0.0489 (8) | 0.0975 (11) | 0.0086 (6) | −0.0029 (7) | 0.0244 (7) |
S3 | 0.0601 (8) | 0.0628 (9) | 0.0715 (9) | −0.0196 (7) | −0.0053 (7) | −0.0103 (7) |
S4 | 0.0594 (8) | 0.0453 (7) | 0.0662 (8) | 0.0158 (6) | 0.0114 (6) | 0.0137 (6) |
C1 | 0.037 (2) | 0.067 (3) | 0.060 (3) | −0.008 (2) | 0.016 (2) | −0.024 (3) |
C2 | 0.058 (3) | 0.078 (4) | 0.093 (4) | 0.017 (3) | 0.022 (3) | −0.022 (3) |
C3 | 0.033 (2) | 0.048 (3) | 0.080 (4) | 0.005 (2) | 0.014 (2) | −0.023 (3) |
C4 | 0.034 (2) | 0.037 (2) | 0.061 (3) | −0.0031 (19) | −0.003 (2) | 0.011 (2) |
C5 | 0.032 (2) | 0.041 (3) | 0.123 (5) | 0.011 (2) | −0.002 (3) | −0.018 (3) |
C6 | 0.033 (2) | 0.039 (2) | 0.075 (3) | 0.0007 (19) | 0.001 (2) | −0.009 (2) |
C7 | 0.046 (2) | 0.044 (3) | 0.051 (3) | −0.008 (2) | 0.016 (2) | −0.009 (2) |
C8 | 0.050 (3) | 0.066 (3) | 0.072 (4) | −0.003 (3) | −0.006 (3) | 0.003 (3) |
C9 | 0.038 (2) | 0.054 (3) | 0.045 (2) | 0.002 (2) | 0.009 (2) | −0.001 (2) |
C10 | 0.046 (2) | 0.039 (2) | 0.050 (3) | 0.008 (2) | 0.013 (2) | 0.0069 (19) |
C11 | 0.044 (3) | 0.054 (3) | 0.058 (3) | 0.010 (2) | 0.003 (2) | 0.004 (2) |
C12 | 0.040 (2) | 0.051 (3) | 0.044 (2) | 0.007 (2) | 0.012 (2) | 0.003 (2) |
C13 | 0.113 (7) | 0.076 (5) | 0.154 (8) | −0.003 (4) | −0.022 (6) | −0.024 (5) |
O1 | 0.068 (2) | 0.052 (2) | 0.104 (3) | 0.0089 (19) | 0.002 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
Mn1—Cl1 | 2.5378 (14) | N8—H8B | 0.8600 |
Mn1—Cl2 | 2.5239 (14) | S1—C2 | 1.726 (7) |
Mn1—N1 | 2.259 (4) | S1—C1 | 1.740 (5) |
Mn1—N2 | 2.247 (3) | S2—C5 | 1.671 (7) |
Mn1—N5 | 2.347 (3) | S2—C4 | 1.736 (5) |
Mn1—N6 | 2.253 (3) | S3—C8 | 1.714 (6) |
N1—C1 | 1.293 (6) | S3—C7 | 1.733 (5) |
N1—C3 | 1.398 (6) | S4—C11 | 1.719 (5) |
N2—C4 | 1.331 (6) | S4—C10 | 1.735 (4) |
N2—C6 | 1.387 (6) | C2—C3 | 1.341 (7) |
N3—C1 | 1.355 (7) | C2—H2 | 0.9300 |
N3—H3A | 0.8600 | C3—C6 | 1.450 (8) |
N3—H3B | 0.8600 | C5—C6 | 1.391 (7) |
N4—C4 | 1.304 (6) | C5—H5 | 0.9300 |
N4—H4A | 0.8600 | C8—C9 | 1.353 (7) |
N4—H4B | 0.8600 | C8—H8 | 0.9300 |
N5—C7 | 1.309 (5) | C9—C12 | 1.455 (6) |
N5—C9 | 1.391 (6) | C11—C12 | 1.338 (6) |
N6—C10 | 1.310 (6) | C11—H11 | 0.9300 |
N6—C12 | 1.393 (5) | C13—O1 | 1.402 (8) |
N7—C7 | 1.336 (6) | C13—H13A | 0.9600 |
N7—H7A | 0.8600 | C13—H13B | 0.9600 |
N7—H7B | 0.8600 | C13—H13C | 0.9600 |
N8—C10 | 1.334 (6) | O1—H1 | 0.8200 |
N8—H8A | 0.8600 | | |
| | | |
N1—Mn1—N2 | 74.07 (14) | N1—C1—N3 | 124.7 (4) |
N1—Mn1—N5 | 84.68 (13) | N1—C1—S1 | 114.5 (4) |
N1—Mn1—N6 | 98.62 (14) | N3—C1—S1 | 120.8 (4) |
N1—Mn1—Cl1 | 170.06 (11) | C3—C2—S1 | 111.3 (5) |
N1—Mn1—Cl2 | 92.41 (10) | C3—C2—H2 | 124.4 |
N2—Mn1—N5 | 96.31 (12) | S1—C2—H2 | 124.4 |
N2—Mn1—N6 | 168.48 (13) | C2—C3—N1 | 114.2 (5) |
N2—Mn1—Cl1 | 97.71 (10) | C2—C3—C6 | 128.7 (5) |
N2—Mn1—Cl2 | 93.34 (10) | N1—C3—C6 | 117.1 (4) |
N5—Mn1—N6 | 73.87 (13) | N4—C4—N2 | 125.1 (4) |
N5—Mn1—Cl1 | 90.81 (9) | N4—C4—S2 | 121.2 (4) |
N5—Mn1—Cl2 | 168.73 (9) | N2—C4—S2 | 113.7 (4) |
N6—Mn1—Cl1 | 88.59 (10) | C6—C5—S2 | 111.7 (4) |
N6—Mn1—Cl2 | 95.88 (10) | C6—C5—H5 | 124.1 |
Cl1—Mn1—Cl2 | 93.66 (5) | S2—C5—H5 | 124.1 |
C1—N1—C3 | 111.4 (4) | N2—C6—C5 | 113.4 (5) |
C1—N1—Mn1 | 132.9 (3) | N2—C6—C3 | 116.6 (4) |
C3—N1—Mn1 | 115.0 (3) | C5—C6—C3 | 130.0 (5) |
C4—N2—C6 | 110.8 (4) | N5—C7—N7 | 124.8 (4) |
C4—N2—Mn1 | 132.2 (3) | N5—C7—S3 | 114.6 (4) |
C6—N2—Mn1 | 116.4 (3) | N7—C7—S3 | 120.6 (3) |
C1—N3—H3A | 120.0 | C9—C8—S3 | 110.6 (4) |
C1—N3—H3B | 120.0 | C9—C8—H8 | 124.7 |
H3A—N3—H3B | 120.0 | S3—C8—H8 | 124.7 |
C4—N4—H4A | 120.0 | C8—C9—N5 | 115.0 (4) |
C4—N4—H4B | 120.0 | C8—C9—C12 | 126.8 (4) |
H4A—N4—H4B | 120.0 | N5—C9—C12 | 118.1 (4) |
C7—N5—C9 | 110.4 (4) | N6—C10—N8 | 125.3 (4) |
C7—N5—Mn1 | 136.9 (3) | N6—C10—S4 | 114.0 (3) |
C9—N5—Mn1 | 112.6 (3) | N8—C10—S4 | 120.6 (3) |
C10—N6—C12 | 110.9 (4) | C12—C11—S4 | 111.1 (4) |
C10—N6—Mn1 | 132.0 (3) | C12—C11—H11 | 124.4 |
C12—N6—Mn1 | 115.0 (3) | S4—C11—H11 | 124.4 |
C7—N7—H7A | 120.0 | C11—C12—N6 | 114.8 (4) |
C7—N7—H7B | 120.0 | C11—C12—C9 | 127.2 (4) |
H7A—N7—H7B | 120.0 | N6—C12—C9 | 117.9 (4) |
C10—N8—H8A | 120.0 | O1—C13—H13A | 109.5 |
C10—N8—H8B | 120.0 | O1—C13—H13B | 109.5 |
H8A—N8—H8B | 120.0 | H13A—C13—H13B | 109.5 |
C2—S1—C1 | 88.6 (3) | O1—C13—H13C | 109.5 |
C5—S2—C4 | 90.2 (2) | H13A—C13—H13C | 109.5 |
C8—S3—C7 | 89.3 (2) | H13B—C13—H13C | 109.5 |
C11—S4—C10 | 89.1 (2) | C13—O1—H1 | 109.5 |
| | | |
N2—Mn1—N1—C1 | 176.5 (4) | C1—N1—C3—C6 | 177.1 (4) |
N6—Mn1—N1—C1 | 5.6 (4) | Mn1—N1—C3—C6 | −10.9 (5) |
N5—Mn1—N1—C1 | 78.4 (4) | C6—N2—C4—N4 | 177.1 (4) |
Cl2—Mn1—N1—C1 | −90.7 (4) | Mn1—N2—C4—N4 | 6.7 (7) |
N2—Mn1—N1—C3 | 6.6 (3) | C6—N2—C4—S2 | −2.0 (5) |
N6—Mn1—N1—C3 | −164.3 (3) | Mn1—N2—C4—S2 | −172.4 (2) |
N5—Mn1—N1—C3 | −91.5 (3) | C5—S2—C4—N4 | −178.6 (4) |
Cl2—Mn1—N1—C3 | 99.4 (3) | C5—S2—C4—N2 | 0.5 (4) |
N6—Mn1—N2—C4 | −139.9 (6) | C4—S2—C5—C6 | 1.1 (4) |
N1—Mn1—N2—C4 | 168.5 (4) | C4—N2—C6—C5 | 2.8 (5) |
N5—Mn1—N2—C4 | −108.9 (4) | Mn1—N2—C6—C5 | 174.9 (3) |
Cl2—Mn1—N2—C4 | 76.9 (4) | C4—N2—C6—C3 | −175.6 (4) |
Cl1—Mn1—N2—C4 | −17.3 (4) | Mn1—N2—C6—C3 | −3.5 (5) |
N6—Mn1—N2—C6 | 50.0 (8) | S2—C5—C6—N2 | −2.4 (5) |
N1—Mn1—N2—C6 | −1.6 (3) | S2—C5—C6—C3 | 175.7 (4) |
N5—Mn1—N2—C6 | 81.0 (3) | C2—C3—C6—N2 | −172.8 (5) |
Cl2—Mn1—N2—C6 | −93.2 (3) | N1—C3—C6—N2 | 9.6 (6) |
Cl1—Mn1—N2—C6 | 172.7 (3) | C2—C3—C6—C5 | 9.1 (9) |
N2—Mn1—N5—C7 | −1.7 (5) | N1—C3—C6—C5 | −168.5 (5) |
N6—Mn1—N5—C7 | 172.2 (5) | C9—N5—C7—N7 | 176.3 (4) |
N1—Mn1—N5—C7 | 71.6 (4) | Mn1—N5—C7—N7 | −6.6 (8) |
Cl2—Mn1—N5—C7 | 147.0 (4) | C9—N5—C7—S3 | −1.8 (5) |
Cl1—Mn1—N5—C7 | −99.6 (4) | Mn1—N5—C7—S3 | 175.3 (2) |
N2—Mn1—N5—C9 | 175.3 (3) | C8—S3—C7—N5 | 1.0 (4) |
N6—Mn1—N5—C9 | −10.8 (3) | C8—S3—C7—N7 | −177.3 (4) |
N1—Mn1—N5—C9 | −111.4 (3) | C7—S3—C8—C9 | 0.2 (5) |
Cl2—Mn1—N5—C9 | −36.0 (6) | S3—C8—C9—N5 | −1.3 (6) |
Cl1—Mn1—N5—C9 | 77.5 (3) | S3—C8—C9—C12 | 176.3 (4) |
N2—Mn1—N6—C10 | −151.9 (6) | C7—N5—C9—C8 | 2.0 (6) |
N1—Mn1—N6—C10 | −102.2 (4) | Mn1—N5—C9—C8 | −175.8 (4) |
N5—Mn1—N6—C10 | 176.0 (4) | C7—N5—C9—C12 | −175.8 (4) |
Cl2—Mn1—N6—C10 | −8.8 (4) | Mn1—N5—C9—C12 | 6.4 (5) |
Cl1—Mn1—N6—C10 | 84.7 (4) | C12—N6—C10—N8 | −179.7 (5) |
N2—Mn1—N6—C12 | 46.4 (8) | Mn1—N6—C10—N8 | 18.0 (7) |
N1—Mn1—N6—C12 | 96.1 (3) | C12—N6—C10—S4 | −1.0 (5) |
N5—Mn1—N6—C12 | 14.3 (3) | Mn1—N6—C10—S4 | −163.3 (2) |
Cl2—Mn1—N6—C12 | −170.5 (3) | C11—S4—C10—N6 | 0.6 (4) |
Cl1—Mn1—N6—C12 | −77.0 (3) | C11—S4—C10—N8 | 179.4 (4) |
C3—N1—C1—N3 | −178.3 (4) | C10—S4—C11—C12 | 0.0 (4) |
Mn1—N1—C1—N3 | 11.6 (7) | S4—C11—C12—N6 | −0.5 (6) |
C3—N1—C1—S1 | 0.8 (5) | S4—C11—C12—C9 | −177.3 (4) |
Mn1—N1—C1—S1 | −169.4 (2) | C10—N6—C12—C11 | 1.0 (6) |
C2—S1—C1—N1 | −0.4 (4) | Mn1—N6—C12—C11 | 166.5 (3) |
C2—S1—C1—N3 | 178.7 (4) | C10—N6—C12—C9 | 178.1 (4) |
C1—S1—C2—C3 | −0.1 (4) | Mn1—N6—C12—C9 | −16.3 (5) |
S1—C2—C3—N1 | 0.5 (6) | C8—C9—C12—C11 | 5.6 (9) |
S1—C2—C3—C6 | −177.1 (4) | N5—C9—C12—C11 | −176.9 (5) |
C1—N1—C3—C2 | −0.8 (6) | C8—C9—C12—N6 | −171.2 (5) |
Mn1—N1—C3—C2 | 171.2 (4) | N5—C9—C12—N6 | 6.3 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1i | 0.82 | 2.38 | 3.197 (4) | 175 |
N3—H3A···N6 | 0.86 | 2.48 | 3.233 (6) | 146 |
N3—H3B···Cl2ii | 0.86 | 2.42 | 3.277 (4) | 173 |
N4—H4A···Cl1 | 0.86 | 2.44 | 3.263 (4) | 160 |
N4—H4B···O1iii | 0.86 | 2.36 | 3.152 (6) | 154 |
N7—H7A···N2 | 0.86 | 2.60 | 3.369 (5) | 150 |
N7—H7B···Cl1iv | 0.86 | 2.52 | 3.364 (4) | 168 |
N8—H8A···Cl2 | 0.86 | 2.35 | 3.144 (4) | 154 |
N8—H8B···O1 | 0.86 | 2.10 | 2.915 (6) | 159 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y−1/2, −z+1/2. |