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In the title coordination polymer, catena-poly[[di­chlorido­manganese(II)]-μ-1,1-diphenyl-3,3′-[(1R,2R)-cyclo­hexane-1,2-diylbis(aza­niumylylidene)]dibut-1-en-1-olate-κ2O:O′], [MnCl2(C26H30N2)]n, synthesized by the reaction of the chiral Schiff base ligand 1,1-diphenyl-3,3′-[(1R,2R)-cyclo­hexane-1,2-diylbis(az­anedi­yl)]dibut-2-en-1-one (L) with MnCl2·4H2O, the asymmetric unit contains one crystallographically unique MnII ion, one unique spacer ligand, L, and two chloride ions. Each MnII ion is four-coordinated in a distorted tetra­hedral coordination environment by two O atoms from two L ligands and by two chloride ligands. The MnII ions are bridged by L ligands to form a one-dimensional chain structure along the a axis. The chloride ligands are monodentate (terminal). The ligand is in the zwitterionic enol form and displays intra­molecular ionic N+—H...O hydrogen bonding and π–π inter­actions between pairs of phenyl rings which strengthen the chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613032531/em3065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613032531/em3065Isup2.hkl
Contains datablock I

CCDC reference: 974514

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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: WinGX (Farrugia, 2012).

catena-Poly[[dichloridomanganese(II)]-µ-1,1-diphenyl-3,3'-[(1R,2R)-cyclohexane-1,2-diylbis(azaniumylylidene)]dibut-1-en-1-olate-κ2O:O'] top
Crystal data top
[MnCl2(C26H30N2)]Z = 2
Mr = 528.36F(000) = 550
Monoclinic, P21Dx = 1.329 Mg m3
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 10.014 (2) ŵ = 0.73 mm1
b = 9.758 (2) ÅT = 293 K
c = 13.667 (3) ÅPrism, colourless
β = 98.668 (8)°0.24 × 0.21 × 0.19 mm
V = 1320.3 (5) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4561 independent reflections
Radiation source: fine-focus sealed tube3732 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scanθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 1211
Tmin = 0.845, Tmax = 0.874k = 1111
14051 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0278P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4561 reflectionsΔρmax = 0.17 e Å3
308 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 1857 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.034 (17)
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
C10.8888 (4)1.2027 (4)0.1018 (3)0.0704 (10)
H10.90921.11000.10920.084*
C20.9884 (4)1.2944 (5)0.0864 (3)0.0849 (13)
H21.07571.26290.08460.102*
C30.9608 (4)1.4302 (5)0.0737 (3)0.0786 (12)
H31.02871.49130.06380.094*
C40.8312 (4)1.4764 (4)0.0757 (3)0.0720 (10)
H40.81101.56880.06550.086*
C50.7311 (3)1.3859 (3)0.0927 (2)0.0597 (9)
H50.64431.41830.09490.072*
C60.7586 (3)1.2477 (3)0.1064 (2)0.0511 (8)
C70.6508 (3)1.1524 (3)0.1296 (2)0.0515 (8)
C80.6513 (3)1.0157 (3)0.1034 (2)0.0542 (8)
H80.71870.98540.06860.065*
C90.5554 (3)0.9189 (3)0.1262 (2)0.0521 (8)
C100.5695 (4)0.7738 (3)0.0927 (3)0.0683 (10)
H10A0.62860.72450.14230.103*
H10B0.60660.77350.03180.103*
H10C0.48240.73060.08240.103*
C110.3570 (3)0.8693 (3)0.2154 (2)0.0492 (7)
H110.34320.78420.17710.059*
C120.2248 (3)0.9485 (4)0.2039 (2)0.0629 (9)
H12A0.19280.96270.13410.075*
H12B0.24081.03780.23470.075*
C130.1163 (3)0.8742 (4)0.2505 (2)0.0702 (10)
H13A0.03560.93050.24470.084*
H13B0.09310.78900.21550.084*
C140.1655 (3)0.8440 (5)0.3590 (2)0.0647 (8)
H14A0.09640.79420.38700.078*
H14B0.18240.92940.39510.078*
C150.2953 (3)0.7590 (3)0.3697 (2)0.0586 (8)
H15A0.32660.74150.43920.070*
H15B0.27680.67150.33680.070*
C160.4051 (3)0.8337 (4)0.32469 (19)0.0468 (7)
H160.42780.91880.36160.056*
C170.7555 (3)0.6792 (3)0.3695 (2)0.0513 (8)
H170.84400.70850.38840.062*
C180.6532 (3)0.7782 (3)0.3664 (2)0.0506 (8)
C190.6890 (4)0.9213 (3)0.4002 (3)0.0693 (10)
H19A0.67390.98240.34450.104*
H19B0.78230.92480.42930.104*
H19C0.63360.94860.44830.104*
N10.4593 (3)0.9523 (3)0.17681 (19)0.0501 (7)
N20.5258 (2)0.7472 (3)0.33332 (18)0.0476 (6)
O10.5573 (2)1.2033 (2)0.17388 (16)0.0616 (6)
Mn10.48719 (4)1.34711 (5)0.26078 (3)0.04734 (13)
Cl10.32663 (8)1.47949 (9)0.16176 (6)0.0657 (2)
Cl20.43128 (8)1.21293 (9)0.38966 (6)0.0611 (2)
C210.8511 (3)0.4439 (3)0.3574 (2)0.0451 (7)
C200.7362 (3)0.5426 (3)0.3471 (2)0.0475 (7)
O20.61624 (19)0.4957 (2)0.31783 (17)0.0607 (6)
C241.0636 (3)0.2581 (4)0.3785 (3)0.0636 (10)
H241.13470.19580.38680.076*
C250.9374 (3)0.2175 (4)0.3932 (3)0.0652 (9)
H250.92330.12730.41120.078*
C231.0850 (3)0.3901 (4)0.3517 (3)0.0686 (10)
H231.17020.41710.33980.082*
C220.9800 (3)0.4836 (3)0.3422 (2)0.0577 (8)
H220.99570.57400.32550.069*
C260.8308 (3)0.3084 (3)0.3817 (2)0.0563 (9)
H260.74500.27880.39020.068*
H1A0.458 (3)1.035 (3)0.1906 (19)0.038 (8)*
H2A0.503 (3)0.654 (4)0.316 (2)0.079 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.059 (2)0.073 (3)0.081 (2)0.006 (2)0.0182 (19)0.008 (2)
C20.052 (2)0.108 (4)0.096 (3)0.003 (2)0.018 (2)0.006 (2)
C30.070 (3)0.090 (4)0.076 (3)0.028 (2)0.011 (2)0.006 (2)
C40.077 (3)0.066 (2)0.075 (2)0.011 (2)0.017 (2)0.004 (2)
C50.060 (2)0.059 (2)0.0632 (19)0.0004 (17)0.0177 (16)0.0039 (16)
C60.054 (2)0.056 (2)0.0446 (17)0.0002 (16)0.0118 (14)0.0012 (15)
C70.057 (2)0.055 (2)0.0436 (17)0.0067 (16)0.0129 (15)0.0004 (14)
C80.059 (2)0.054 (2)0.0539 (18)0.0068 (16)0.0236 (15)0.0034 (15)
C90.056 (2)0.052 (2)0.0485 (18)0.0103 (15)0.0083 (16)0.0064 (15)
C100.076 (3)0.052 (2)0.079 (2)0.0032 (18)0.020 (2)0.0127 (18)
C110.0494 (16)0.0426 (19)0.0555 (16)0.0036 (15)0.0068 (13)0.0035 (14)
C120.058 (2)0.066 (2)0.062 (2)0.0052 (18)0.0017 (16)0.0059 (17)
C130.0471 (18)0.077 (3)0.086 (2)0.0031 (19)0.0085 (16)0.006 (2)
C140.0492 (17)0.067 (2)0.080 (2)0.001 (2)0.0154 (15)0.006 (2)
C150.054 (2)0.055 (2)0.067 (2)0.0028 (16)0.0117 (16)0.0074 (16)
C160.0427 (15)0.0422 (17)0.0554 (16)0.0017 (16)0.0072 (12)0.0009 (16)
C170.0346 (16)0.049 (2)0.067 (2)0.0084 (14)0.0023 (14)0.0025 (15)
C180.051 (2)0.0446 (18)0.0539 (18)0.0047 (14)0.0007 (15)0.0012 (14)
C190.059 (2)0.044 (2)0.100 (3)0.0091 (16)0.0043 (19)0.0098 (19)
N10.0599 (17)0.0355 (16)0.0570 (16)0.0022 (13)0.0159 (13)0.0019 (12)
N20.0423 (15)0.0394 (16)0.0593 (15)0.0008 (12)0.0016 (12)0.0015 (12)
O10.0683 (14)0.0472 (12)0.0774 (14)0.0002 (11)0.0368 (12)0.0076 (11)
Mn10.0409 (2)0.0408 (2)0.0614 (3)0.0036 (2)0.01121 (18)0.0069 (2)
Cl10.0547 (5)0.0699 (6)0.0698 (5)0.0008 (4)0.0009 (4)0.0060 (4)
Cl20.0595 (5)0.0609 (5)0.0653 (5)0.0011 (4)0.0170 (4)0.0038 (4)
C210.0376 (17)0.0477 (18)0.0491 (17)0.0019 (14)0.0035 (13)0.0011 (14)
C200.0412 (17)0.0507 (19)0.0497 (17)0.0070 (14)0.0038 (13)0.0020 (14)
O20.0372 (11)0.0454 (13)0.0959 (15)0.0056 (10)0.0021 (10)0.0128 (11)
C240.046 (2)0.066 (3)0.077 (2)0.0108 (18)0.0070 (17)0.0047 (19)
C250.058 (2)0.053 (2)0.083 (2)0.0041 (18)0.0060 (18)0.0072 (18)
C230.0420 (19)0.077 (3)0.088 (2)0.0017 (17)0.0166 (17)0.0029 (19)
C220.0449 (19)0.053 (2)0.077 (2)0.0020 (16)0.0126 (16)0.0050 (17)
C260.0415 (18)0.054 (2)0.072 (2)0.0025 (15)0.0055 (15)0.0062 (15)
Geometric parameters (Å, º) top
C1—C21.380 (5)C15—C161.524 (4)
C1—C61.386 (5)C15—H15A0.9700
C1—H10.9300C15—H15B0.9700
C2—C31.359 (5)C16—N21.465 (3)
C2—H20.9300C16—H160.9800
C3—C41.378 (5)C17—C201.374 (4)
C3—H30.9300C17—C181.404 (4)
C4—C51.381 (5)C17—H170.9300
C4—H40.9300C18—N21.323 (4)
C5—C61.384 (4)C18—C191.497 (4)
C5—H50.9300C19—H19A0.9600
C6—C71.494 (4)C19—H19B0.9600
C7—O11.289 (3)C19—H19C0.9600
C7—C81.382 (4)N1—H1A0.83 (3)
C8—C91.415 (4)N2—H2A0.95 (4)
C8—H80.9300O1—Mn12.031 (2)
C9—N11.308 (4)Mn1—O2i2.0192 (19)
C9—C101.502 (4)Mn1—Cl22.3298 (10)
C10—H10A0.9600Mn1—Cl12.3301 (10)
C10—H10B0.9600C21—C261.385 (4)
C10—H10C0.9600C21—C221.394 (4)
C11—N11.465 (4)C21—C201.490 (4)
C11—C121.520 (4)C20—O21.291 (3)
C11—C161.538 (4)O2—Mn1ii2.0192 (19)
C11—H110.9800C24—C231.365 (5)
C12—C131.524 (4)C24—C251.368 (5)
C12—H12A0.9700C24—H240.9300
C12—H12B0.9700C25—C261.379 (4)
C13—C141.519 (4)C25—H250.9300
C13—H13A0.9700C23—C221.384 (5)
C13—H13B0.9700C23—H230.9300
C14—C151.531 (4)C22—H220.9300
C14—H14A0.9700C26—H260.9300
C14—H14B0.9700
C2—C1—C6120.6 (4)C16—C15—H15A109.5
C2—C1—H1119.7C14—C15—H15A109.5
C6—C1—H1119.7C16—C15—H15B109.5
C3—C2—C1120.9 (4)C14—C15—H15B109.5
C3—C2—H2119.6H15A—C15—H15B108.1
C1—C2—H2119.6N2—C16—C15109.2 (3)
C2—C3—C4119.4 (4)N2—C16—C11110.0 (2)
C2—C3—H3120.3C15—C16—C11111.1 (2)
C4—C3—H3120.3N2—C16—H16108.8
C3—C4—C5120.2 (4)C15—C16—H16108.8
C3—C4—H4119.9C11—C16—H16108.8
C5—C4—H4119.9C20—C17—C18125.7 (3)
C4—C5—C6120.7 (4)C20—C17—H17117.2
C4—C5—H5119.6C18—C17—H17117.2
C6—C5—H5119.6N2—C18—C17120.9 (3)
C5—C6—C1118.2 (3)N2—C18—C19119.5 (3)
C5—C6—C7120.0 (3)C17—C18—C19119.6 (3)
C1—C6—C7121.8 (3)C18—C19—H19A109.5
O1—C7—C8121.6 (3)C18—C19—H19B109.5
O1—C7—C6117.3 (3)H19A—C19—H19B109.5
C8—C7—C6121.0 (3)C18—C19—H19C109.5
C7—C8—C9124.0 (3)H19A—C19—H19C109.5
C7—C8—H8118.0H19B—C19—H19C109.5
C9—C8—H8118.0C9—N1—C11131.5 (3)
N1—C9—C8121.9 (3)C9—N1—H1A113.7 (19)
N1—C9—C10120.5 (3)C11—N1—H1A114.8 (19)
C8—C9—C10117.6 (3)C18—N2—C16129.6 (3)
C9—C10—H10A109.5C18—N2—H2A119 (2)
C9—C10—H10B109.5C16—N2—H2A111 (2)
H10A—C10—H10B109.5C7—O1—Mn1151.7 (2)
C9—C10—H10C109.5O2i—Mn1—O1117.68 (9)
H10A—C10—H10C109.5O2i—Mn1—Cl2108.93 (7)
H10B—C10—H10C109.5O1—Mn1—Cl2101.38 (7)
N1—C11—C12109.1 (3)O2i—Mn1—Cl199.88 (7)
N1—C11—C16109.9 (2)O1—Mn1—Cl1108.22 (7)
C12—C11—C16110.8 (2)Cl2—Mn1—Cl1121.82 (4)
N1—C11—H11109.0C26—C21—C22118.3 (3)
C12—C11—H11109.0C26—C21—C20120.0 (3)
C16—C11—H11109.0C22—C21—C20121.7 (3)
C11—C12—C13112.3 (3)O2—C20—C17120.4 (3)
C11—C12—H12A109.1O2—C20—C21117.9 (3)
C13—C12—H12A109.1C17—C20—C21121.6 (3)
C11—C12—H12B109.1C20—O2—Mn1ii152.3 (2)
C13—C12—H12B109.1C23—C24—C25119.9 (4)
H12A—C12—H12B107.9C23—C24—H24120.0
C14—C13—C12110.7 (3)C25—C24—H24120.0
C14—C13—H13A109.5C24—C25—C26120.9 (3)
C12—C13—H13A109.5C24—C25—H25119.6
C14—C13—H13B109.5C26—C25—H25119.6
C12—C13—H13B109.5C24—C23—C22120.0 (3)
H13A—C13—H13B108.1C24—C23—H23120.0
C13—C14—C15110.1 (3)C22—C23—H23120.0
C13—C14—H14A109.6C23—C22—C21120.7 (3)
C15—C14—H14A109.6C23—C22—H22119.6
C13—C14—H14B109.6C21—C22—H22119.6
C15—C14—H14B109.6C25—C26—C21120.2 (3)
H14A—C14—H14B108.2C25—C26—H26119.9
C16—C15—C14110.9 (3)C21—C26—H26119.9
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.95 (4)1.92 (3)2.635 (3)130 (3)
N1—H1A···O10.83 (3)1.95 (3)2.641 (4)140 (2)
 

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