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The title compound, [MnCl2(C24H20N6)], has been synthesized and characterized based on the multifunctional ligand 2,5-bis­(2,2′-bipyridyl-6-yl)-3,4-di­aza­hexa-2,4-diene (L). The MnII centre is five-coordinate with an approximately square-pyramidal geometry. The L ligand acts as a tridendate chelating ligand. The mononuclear mol­ecules are bridged into a one-dimensional chain by two C—H...Cl hydrogen bonds. These chains are assembled into a two-dimensional layer through π–π stacking inter­actions between adjacent uncoordinated bipyridyl groups. Furthermore, a three-dimensional supra­molecular framework is attained through π–π stacking inter­actions between adjacent coordinated bipyridyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614014107/dt3025sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614014107/dt3025Isup2.hkl
Contains datablock I

CCDC reference: 1008615

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

[2,5-Bis(2,2'-bipyridyl-6-yl)-3,4-diazahexa-2,4-diene]dichloridomanganese(II) top
Crystal data top
[MnCl2(C24H20N6)]Z = 2
Mr = 518.30F(000) = 530
Triclinic, P1Dx = 1.504 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5761 (5) ÅCell parameters from 3657 reflections
b = 8.9118 (6) Åθ = 1.8–28.1°
c = 16.4088 (9) ŵ = 0.84 mm1
α = 96.192 (5)°T = 293 K
β = 91.571 (5)°Block, yellow
γ = 112.971 (6)°0.43 × 0.32 × 0.21 mm
V = 1144.60 (12) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4988 independent reflections
Radiation source: fine-focus sealed tube3957 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
phi and ω scansθmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.715, Tmax = 0.844k = 1111
12249 measured reflectionsl = 2120
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.269P]
where P = (Fo2 + 2Fc2)/3
4988 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Mn10.78759 (4)0.86477 (4)0.15374 (2)0.03328 (11)
Cl10.83218 (8)0.72832 (8)0.03265 (4)0.05034 (17)
Cl21.03731 (7)1.05279 (8)0.22726 (4)0.05485 (18)
N10.6869 (2)1.0471 (2)0.11529 (11)0.0386 (4)
N20.5119 (2)0.7663 (2)0.16748 (10)0.0325 (4)
N31.5187 (2)0.7658 (3)0.53975 (13)0.0472 (5)
N41.1238 (2)0.7012 (2)0.43725 (11)0.0349 (4)
N50.7113 (2)0.6522 (2)0.23554 (10)0.0346 (4)
N60.8238 (2)0.5949 (2)0.27018 (11)0.0362 (4)
C10.5176 (3)1.0052 (3)0.11365 (13)0.0371 (5)
C20.4443 (3)1.1083 (3)0.08980 (14)0.0490 (6)
H2A0.32731.07720.08870.059*
C30.5471 (4)1.2576 (3)0.06773 (16)0.0557 (7)
H3A0.50011.32890.05170.067*
C40.7193 (4)1.3013 (3)0.06939 (16)0.0547 (7)
H4A0.79071.40210.05470.066*
C50.7840 (3)1.1924 (3)0.09338 (15)0.0488 (6)
H5A0.90081.22160.09430.059*
C60.4194 (3)0.8425 (3)0.13885 (12)0.0362 (5)
C70.2418 (3)0.7690 (3)0.13465 (15)0.0479 (6)
H7A0.17710.82300.11590.058*
C80.1654 (3)0.6166 (4)0.15854 (16)0.0556 (7)
H8A0.04760.56500.15480.067*
C90.2615 (3)0.5386 (3)0.18805 (15)0.0488 (6)
H9A0.21000.43450.20410.059*
C100.4365 (3)0.6189 (3)0.19322 (13)0.0354 (5)
C110.5536 (3)0.5565 (3)0.23152 (13)0.0350 (5)
C120.4890 (3)0.3989 (3)0.26731 (16)0.0509 (6)
H12A0.56790.34720.26030.076*
H12B0.38090.32760.23990.076*
H12C0.47640.42030.32480.076*
C131.3679 (3)0.7755 (3)0.53166 (13)0.0364 (5)
C141.3289 (3)0.8909 (3)0.57955 (15)0.0506 (6)
H14A1.22320.89580.57190.061*
C151.4475 (4)0.9985 (3)0.63863 (17)0.0603 (7)
H15A1.42221.07510.67260.072*
C161.6039 (3)0.9915 (3)0.64691 (16)0.0540 (7)
H16A1.68751.06380.68590.065*
C171.6328 (3)0.8755 (3)0.59629 (17)0.0524 (7)
H17A1.73970.87230.60140.063*
C181.2423 (3)0.6553 (3)0.46790 (13)0.0354 (5)
C191.2477 (3)0.5049 (3)0.44196 (14)0.0439 (6)
H19A1.33130.47590.46410.053*
C201.1268 (3)0.3989 (3)0.38278 (15)0.0486 (6)
H20A1.12580.29540.36590.058*
C211.0079 (3)0.4461 (3)0.34875 (14)0.0418 (5)
H21A0.92730.37730.30760.050*
C221.0118 (3)0.5996 (3)0.37778 (12)0.0338 (5)
C230.8898 (3)0.6617 (3)0.34265 (13)0.0351 (5)
C240.8527 (3)0.7912 (3)0.39300 (14)0.0500 (6)
H24A0.86530.87910.36120.075*
H24B0.93050.83290.44110.075*
H24C0.73850.74530.40910.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02291 (17)0.03437 (19)0.0404 (2)0.00969 (13)0.00259 (13)0.00334 (14)
Cl10.0534 (4)0.0571 (4)0.0457 (3)0.0289 (3)0.0036 (3)0.0012 (3)
Cl20.0396 (3)0.0465 (4)0.0632 (4)0.0046 (3)0.0173 (3)0.0027 (3)
N10.0334 (10)0.0389 (11)0.0434 (11)0.0148 (8)0.0029 (8)0.0048 (8)
N20.0252 (9)0.0402 (10)0.0313 (9)0.0129 (8)0.0009 (7)0.0017 (8)
N30.0411 (11)0.0517 (12)0.0546 (13)0.0241 (10)0.0043 (9)0.0102 (10)
N40.0348 (10)0.0377 (10)0.0363 (10)0.0187 (8)0.0012 (8)0.0058 (8)
N50.0307 (9)0.0370 (10)0.0349 (10)0.0120 (8)0.0029 (7)0.0059 (8)
N60.0322 (9)0.0376 (10)0.0393 (10)0.0143 (8)0.0012 (8)0.0064 (8)
C10.0373 (12)0.0455 (13)0.0313 (11)0.0219 (10)0.0055 (9)0.0035 (10)
C20.0512 (15)0.0592 (17)0.0452 (14)0.0344 (13)0.0094 (11)0.0028 (12)
C30.0754 (19)0.0559 (17)0.0487 (15)0.0430 (15)0.0153 (13)0.0016 (13)
C40.0729 (19)0.0394 (14)0.0490 (15)0.0201 (13)0.0097 (13)0.0055 (12)
C50.0449 (14)0.0429 (14)0.0551 (15)0.0138 (11)0.0061 (11)0.0081 (12)
C60.0299 (11)0.0504 (14)0.0304 (11)0.0201 (10)0.0020 (9)0.0010 (10)
C70.0307 (12)0.0710 (18)0.0451 (14)0.0256 (12)0.0052 (10)0.0008 (12)
C80.0236 (12)0.078 (2)0.0557 (16)0.0100 (12)0.0008 (11)0.0091 (14)
C90.0293 (12)0.0608 (16)0.0455 (14)0.0053 (11)0.0030 (10)0.0101 (12)
C100.0272 (11)0.0433 (13)0.0300 (11)0.0085 (9)0.0014 (8)0.0022 (9)
C110.0319 (11)0.0370 (12)0.0320 (11)0.0091 (9)0.0022 (9)0.0042 (9)
C120.0430 (14)0.0439 (14)0.0607 (16)0.0089 (11)0.0071 (12)0.0170 (12)
C130.0383 (12)0.0402 (13)0.0344 (12)0.0189 (10)0.0018 (9)0.0081 (10)
C140.0455 (14)0.0562 (16)0.0542 (15)0.0287 (12)0.0094 (12)0.0063 (12)
C150.0660 (18)0.0606 (18)0.0563 (17)0.0334 (15)0.0131 (14)0.0116 (14)
C160.0543 (16)0.0477 (15)0.0510 (15)0.0116 (12)0.0158 (12)0.0075 (12)
C170.0391 (13)0.0543 (16)0.0648 (17)0.0185 (12)0.0106 (12)0.0157 (14)
C180.0367 (12)0.0428 (13)0.0326 (11)0.0214 (10)0.0038 (9)0.0076 (10)
C190.0491 (14)0.0480 (14)0.0450 (13)0.0306 (12)0.0006 (11)0.0062 (11)
C200.0632 (16)0.0437 (14)0.0493 (15)0.0336 (13)0.0001 (12)0.0017 (12)
C210.0455 (13)0.0428 (13)0.0395 (13)0.0211 (11)0.0026 (10)0.0018 (10)
C220.0339 (11)0.0379 (12)0.0325 (11)0.0167 (9)0.0046 (9)0.0067 (9)
C230.0311 (11)0.0375 (12)0.0384 (12)0.0147 (9)0.0033 (9)0.0071 (10)
C240.0574 (16)0.0623 (17)0.0419 (14)0.0394 (14)0.0056 (12)0.0035 (12)
Geometric parameters (Å, º) top
Mn1—N12.2519 (17)C8—H8A0.9300
Mn1—N22.2058 (16)C9—C101.383 (3)
Mn1—N52.3338 (17)C9—H9A0.9300
Mn1—Cl12.3358 (7)C10—C111.480 (3)
Mn1—Cl22.3391 (7)C11—C121.487 (3)
N1—C51.332 (3)C12—H12A0.9600
N1—C11.350 (3)C12—H12B0.9600
N2—C61.334 (3)C12—H12C0.9600
N2—C101.339 (3)C13—C141.377 (3)
N3—C131.333 (3)C13—C181.483 (3)
N3—C171.335 (3)C14—C151.370 (4)
N4—C221.332 (3)C14—H14A0.9300
N4—C181.339 (2)C15—C161.371 (4)
N5—C111.283 (3)C15—H15A0.9300
N5—N61.390 (2)C16—C171.359 (4)
N6—C231.279 (3)C16—H16A0.9300
C1—C21.381 (3)C17—H17A0.9300
C1—C61.476 (3)C18—C191.381 (3)
C2—C31.373 (4)C19—C201.376 (3)
C2—H2A0.9300C19—H19A0.9300
C3—C41.371 (4)C20—C211.372 (3)
C3—H3A0.9300C20—H20A0.9300
C4—C51.377 (3)C21—C221.387 (3)
C4—H4A0.9300C21—H21A0.9300
C5—H5A0.9300C22—C231.491 (3)
C6—C71.399 (3)C23—C241.487 (3)
C7—C81.365 (4)C24—H24A0.9600
C7—H7A0.9300C24—H24B0.9600
C8—C91.376 (4)C24—H24C0.9600
N1—Mn1—N271.90 (7)N2—C10—C11114.95 (17)
N1—Mn1—N5138.36 (7)C9—C10—C11123.7 (2)
N2—Mn1—N569.49 (6)N5—C11—C10115.11 (19)
N1—Mn1—Cl1106.34 (5)N5—C11—C12123.34 (19)
N2—Mn1—Cl1107.70 (5)C10—C11—C12121.43 (19)
N5—Mn1—Cl199.73 (5)C11—C12—H12A109.5
N1—Mn1—Cl297.77 (5)C11—C12—H12B109.5
N2—Mn1—Cl2138.17 (5)H12A—C12—H12B109.5
N5—Mn1—Cl2100.53 (5)C11—C12—H12C109.5
Cl1—Mn1—Cl2114.07 (3)H12A—C12—H12C109.5
C5—N1—C1118.32 (19)H12B—C12—H12C109.5
C5—N1—Mn1123.99 (15)N3—C13—C14122.3 (2)
C1—N1—Mn1117.70 (15)N3—C13—C18116.75 (19)
C6—N2—C10120.60 (18)C14—C13—C18120.92 (19)
C6—N2—Mn1119.37 (15)C15—C14—C13119.3 (2)
C10—N2—Mn1119.29 (13)C15—C14—H14A120.4
C13—N3—C17116.8 (2)C13—C14—H14A120.4
C22—N4—C18118.27 (18)C14—C15—C16119.1 (2)
C11—N5—N6116.08 (17)C14—C15—H15A120.5
C11—N5—Mn1116.89 (13)C16—C15—H15A120.5
N6—N5—Mn1124.71 (12)C17—C16—C15117.9 (2)
C23—N6—N5116.58 (17)C17—C16—H16A121.1
N1—C1—C2121.7 (2)C15—C16—H16A121.1
N1—C1—C6114.86 (18)N3—C17—C16124.6 (2)
C2—C1—C6123.4 (2)N3—C17—H17A117.7
C3—C2—C1118.9 (2)C16—C17—H17A117.7
C3—C2—H2A120.6N4—C18—C19122.2 (2)
C1—C2—H2A120.6N4—C18—C13116.17 (18)
C4—C3—C2119.8 (2)C19—C18—C13121.65 (18)
C4—C3—H3A120.1C20—C19—C18118.7 (2)
C2—C3—H3A120.1C20—C19—H19A120.6
C3—C4—C5118.4 (2)C18—C19—H19A120.6
C3—C4—H4A120.8C21—C20—C19119.8 (2)
C5—C4—H4A120.8C21—C20—H20A120.1
N1—C5—C4122.9 (2)C19—C20—H20A120.1
N1—C5—H5A118.5C20—C21—C22117.9 (2)
C4—C5—H5A118.5C20—C21—H21A121.1
N2—C6—C7120.5 (2)C22—C21—H21A121.1
N2—C6—C1115.30 (18)N4—C22—C21123.04 (19)
C7—C6—C1124.2 (2)N4—C22—C23115.78 (18)
C8—C7—C6118.7 (2)C21—C22—C23121.2 (2)
C8—C7—H7A120.6N6—C23—C24125.52 (19)
C6—C7—H7A120.6N6—C23—C22115.43 (18)
C7—C8—C9120.5 (2)C24—C23—C22119.05 (19)
C7—C8—H8A119.7C23—C24—H24A109.5
C9—C8—H8A119.7C23—C24—H24B109.5
C8—C9—C10118.4 (2)H24A—C24—H24B109.5
C8—C9—H9A120.8C23—C24—H24C109.5
C10—C9—H9A120.8H24A—C24—H24C109.5
N2—C10—C9121.2 (2)H24B—C24—H24C109.5
N2—Mn1—N1—C5176.3 (2)C1—C6—C7—C8178.9 (2)
N5—Mn1—N1—C5153.50 (17)C6—C7—C8—C91.6 (4)
Cl1—Mn1—N1—C580.01 (19)C7—C8—C9—C100.3 (4)
Cl2—Mn1—N1—C537.96 (19)C6—N2—C10—C92.5 (3)
N2—Mn1—N1—C14.48 (15)Mn1—N2—C10—C9167.65 (17)
N5—Mn1—N1—C127.2 (2)C6—N2—C10—C11173.82 (18)
Cl1—Mn1—N1—C199.26 (15)Mn1—N2—C10—C1116.1 (2)
Cl2—Mn1—N1—C1142.77 (15)C8—C9—C10—N22.4 (4)
N1—Mn1—N2—C68.31 (15)C8—C9—C10—C11173.6 (2)
N5—Mn1—N2—C6172.38 (17)N6—N5—C11—C10179.06 (17)
Cl1—Mn1—N2—C693.61 (15)Mn1—N5—C11—C1015.5 (2)
Cl2—Mn1—N2—C689.58 (16)N6—N5—C11—C124.9 (3)
N1—Mn1—N2—C10178.55 (17)Mn1—N5—C11—C12168.42 (17)
N5—Mn1—N2—C1017.38 (15)N2—C10—C11—N50.5 (3)
Cl1—Mn1—N2—C1076.64 (15)C9—C10—C11—N5175.7 (2)
Cl2—Mn1—N2—C10100.18 (16)N2—C10—C11—C12176.6 (2)
N2—Mn1—N5—C1117.58 (15)C9—C10—C11—C120.4 (3)
N1—Mn1—N5—C1140.7 (2)C17—N3—C13—C140.8 (3)
Cl1—Mn1—N5—C1187.80 (16)C17—N3—C13—C18179.0 (2)
Cl2—Mn1—N5—C11155.28 (15)N3—C13—C14—C151.1 (4)
N2—Mn1—N5—N6179.53 (17)C18—C13—C14—C15179.1 (2)
N1—Mn1—N5—N6157.36 (14)C13—C14—C15—C161.9 (4)
Cl1—Mn1—N5—N674.14 (15)C14—C15—C16—C170.9 (4)
Cl2—Mn1—N5—N642.77 (16)C13—N3—C17—C161.9 (4)
C11—N5—N6—C23106.2 (2)C15—C16—C17—N31.1 (4)
Mn1—N5—N6—C2391.7 (2)C22—N4—C18—C192.4 (3)
C5—N1—C1—C20.2 (3)C22—N4—C18—C13177.71 (18)
Mn1—N1—C1—C2179.11 (16)N3—C13—C18—N4154.5 (2)
C5—N1—C1—C6180.0 (2)C14—C13—C18—N425.4 (3)
Mn1—N1—C1—C60.7 (2)N3—C13—C18—C1925.6 (3)
N1—C1—C2—C30.4 (3)C14—C13—C18—C19154.6 (2)
C6—C1—C2—C3179.8 (2)N4—C18—C19—C200.1 (3)
C1—C2—C3—C40.2 (4)C13—C18—C19—C20179.8 (2)
C2—C3—C4—C50.1 (4)C18—C19—C20—C212.3 (4)
C1—N1—C5—C40.1 (4)C19—C20—C21—C221.9 (4)
Mn1—N1—C5—C4179.41 (18)C18—N4—C22—C212.8 (3)
C3—C4—C5—N10.3 (4)C18—N4—C22—C23176.42 (18)
C10—N2—C6—C70.5 (3)C20—C21—C22—N40.7 (3)
Mn1—N2—C6—C7169.65 (16)C20—C21—C22—C23178.5 (2)
C10—N2—C6—C1179.11 (18)N5—N6—C23—C241.6 (3)
Mn1—N2—C6—C110.8 (2)N5—N6—C23—C22179.15 (17)
N1—C1—C6—N26.4 (3)N4—C22—C23—N6157.11 (19)
C2—C1—C6—N2173.8 (2)C21—C22—C23—N622.2 (3)
N1—C1—C6—C7174.1 (2)N4—C22—C23—C2423.6 (3)
C2—C1—C6—C75.8 (3)C21—C22—C23—C24157.1 (2)
N2—C6—C7—C81.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···Cl1i0.932.853.665 (3)147
C20—H20A···Cl2ii0.932.833.600 (3)141
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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