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In the title coordination polymer,
catena-poly[[dichloridomanganese(II)]-μ-1,1-diphenyl-3,3′-[(1
R,2
R)-cyclohexane-1,2-diylbis(azaniumylylidene)]dibut-1-en-1-olate-κ
2O:
O′], [MnCl
2(C
26H
30N
2)]
n, synthesized by the reaction of the chiral Schiff base ligand 1,1-diphenyl-3,3′-[(1
R,2
R)-cyclohexane-1,2-diylbis(azanediyl)]dibut-2-en-1-one (
L) with MnCl
2·4H
2O, the asymmetric unit contains one crystallographically unique Mn
II ion, one unique spacer ligand,
L, and two chloride ions. Each Mn
II ion is four-coordinated in a distorted tetrahedral coordination environment by two O atoms from two
L ligands and by two chloride ligands. The Mn
II 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
CCDC reference: 974514
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'-[(1
R,2
R)-cyclohexane-1,2-diylbis(azaniumylylidene)]dibut-1-en-1-olate-
κ2O:
O']
top
Crystal data top
[MnCl2(C26H30N2)] | Z = 2 |
Mr = 528.36 | F(000) = 550 |
Monoclinic, P21 | Dx = 1.329 Mg m−3 |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 10.014 (2) Å | µ = 0.73 mm−1 |
b = 9.758 (2) Å | T = 293 K |
c = 13.667 (3) Å | Prism, 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 tube | 3732 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scan | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −12→11 |
Tmin = 0.845, Tmax = 0.874 | k = −11→11 |
14051 measured reflections | l = −16→16 |
Refinement top
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)] = 0.035 | H 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 reflections | Δρmax = 0.17 e Å−3 |
308 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1857 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.8888 (4) | 1.2027 (4) | 0.1018 (3) | 0.0704 (10) | |
H1 | 0.9092 | 1.1100 | 0.1092 | 0.084* | |
C2 | 0.9884 (4) | 1.2944 (5) | 0.0864 (3) | 0.0849 (13) | |
H2 | 1.0757 | 1.2629 | 0.0846 | 0.102* | |
C3 | 0.9608 (4) | 1.4302 (5) | 0.0737 (3) | 0.0786 (12) | |
H3 | 1.0287 | 1.4913 | 0.0638 | 0.094* | |
C4 | 0.8312 (4) | 1.4764 (4) | 0.0757 (3) | 0.0720 (10) | |
H4 | 0.8110 | 1.5688 | 0.0655 | 0.086* | |
C5 | 0.7311 (3) | 1.3859 (3) | 0.0927 (2) | 0.0597 (9) | |
H5 | 0.6443 | 1.4183 | 0.0949 | 0.072* | |
C6 | 0.7586 (3) | 1.2477 (3) | 0.1064 (2) | 0.0511 (8) | |
C7 | 0.6508 (3) | 1.1524 (3) | 0.1296 (2) | 0.0515 (8) | |
C8 | 0.6513 (3) | 1.0157 (3) | 0.1034 (2) | 0.0542 (8) | |
H8 | 0.7187 | 0.9854 | 0.0686 | 0.065* | |
C9 | 0.5554 (3) | 0.9189 (3) | 0.1262 (2) | 0.0521 (8) | |
C10 | 0.5695 (4) | 0.7738 (3) | 0.0927 (3) | 0.0683 (10) | |
H10A | 0.6286 | 0.7245 | 0.1423 | 0.103* | |
H10B | 0.6066 | 0.7735 | 0.0318 | 0.103* | |
H10C | 0.4824 | 0.7306 | 0.0824 | 0.103* | |
C11 | 0.3570 (3) | 0.8693 (3) | 0.2154 (2) | 0.0492 (7) | |
H11 | 0.3432 | 0.7842 | 0.1771 | 0.059* | |
C12 | 0.2248 (3) | 0.9485 (4) | 0.2039 (2) | 0.0629 (9) | |
H12A | 0.1928 | 0.9627 | 0.1341 | 0.075* | |
H12B | 0.2408 | 1.0378 | 0.2347 | 0.075* | |
C13 | 0.1163 (3) | 0.8742 (4) | 0.2505 (2) | 0.0702 (10) | |
H13A | 0.0356 | 0.9305 | 0.2447 | 0.084* | |
H13B | 0.0931 | 0.7890 | 0.2155 | 0.084* | |
C14 | 0.1655 (3) | 0.8440 (5) | 0.3590 (2) | 0.0647 (8) | |
H14A | 0.0964 | 0.7942 | 0.3870 | 0.078* | |
H14B | 0.1824 | 0.9294 | 0.3951 | 0.078* | |
C15 | 0.2953 (3) | 0.7590 (3) | 0.3697 (2) | 0.0586 (8) | |
H15A | 0.3266 | 0.7415 | 0.4392 | 0.070* | |
H15B | 0.2768 | 0.6715 | 0.3368 | 0.070* | |
C16 | 0.4051 (3) | 0.8337 (4) | 0.32469 (19) | 0.0468 (7) | |
H16 | 0.4278 | 0.9188 | 0.3616 | 0.056* | |
C17 | 0.7555 (3) | 0.6792 (3) | 0.3695 (2) | 0.0513 (8) | |
H17 | 0.8440 | 0.7085 | 0.3884 | 0.062* | |
C18 | 0.6532 (3) | 0.7782 (3) | 0.3664 (2) | 0.0506 (8) | |
C19 | 0.6890 (4) | 0.9213 (3) | 0.4002 (3) | 0.0693 (10) | |
H19A | 0.6739 | 0.9824 | 0.3445 | 0.104* | |
H19B | 0.7823 | 0.9248 | 0.4293 | 0.104* | |
H19C | 0.6336 | 0.9486 | 0.4483 | 0.104* | |
N1 | 0.4593 (3) | 0.9523 (3) | 0.17681 (19) | 0.0501 (7) | |
N2 | 0.5258 (2) | 0.7472 (3) | 0.33332 (18) | 0.0476 (6) | |
O1 | 0.5573 (2) | 1.2033 (2) | 0.17388 (16) | 0.0616 (6) | |
Mn1 | 0.48719 (4) | 1.34711 (5) | 0.26078 (3) | 0.04734 (13) | |
Cl1 | 0.32663 (8) | 1.47949 (9) | 0.16176 (6) | 0.0657 (2) | |
Cl2 | 0.43128 (8) | 1.21293 (9) | 0.38966 (6) | 0.0611 (2) | |
C21 | 0.8511 (3) | 0.4439 (3) | 0.3574 (2) | 0.0451 (7) | |
C20 | 0.7362 (3) | 0.5426 (3) | 0.3471 (2) | 0.0475 (7) | |
O2 | 0.61624 (19) | 0.4957 (2) | 0.31783 (17) | 0.0607 (6) | |
C24 | 1.0636 (3) | 0.2581 (4) | 0.3785 (3) | 0.0636 (10) | |
H24 | 1.1347 | 0.1958 | 0.3868 | 0.076* | |
C25 | 0.9374 (3) | 0.2175 (4) | 0.3932 (3) | 0.0652 (9) | |
H25 | 0.9233 | 0.1273 | 0.4112 | 0.078* | |
C23 | 1.0850 (3) | 0.3901 (4) | 0.3517 (3) | 0.0686 (10) | |
H23 | 1.1702 | 0.4171 | 0.3398 | 0.082* | |
C22 | 0.9800 (3) | 0.4836 (3) | 0.3422 (2) | 0.0577 (8) | |
H22 | 0.9957 | 0.5740 | 0.3255 | 0.069* | |
C26 | 0.8308 (3) | 0.3084 (3) | 0.3817 (2) | 0.0563 (9) | |
H26 | 0.7450 | 0.2788 | 0.3902 | 0.068* | |
H1A | 0.458 (3) | 1.035 (3) | 0.1906 (19) | 0.038 (8)* | |
H2A | 0.503 (3) | 0.654 (4) | 0.316 (2) | 0.079 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.059 (2) | 0.073 (3) | 0.081 (2) | 0.006 (2) | 0.0182 (19) | 0.008 (2) |
C2 | 0.052 (2) | 0.108 (4) | 0.096 (3) | 0.003 (2) | 0.018 (2) | 0.006 (2) |
C3 | 0.070 (3) | 0.090 (4) | 0.076 (3) | −0.028 (2) | 0.011 (2) | 0.006 (2) |
C4 | 0.077 (3) | 0.066 (2) | 0.075 (2) | −0.011 (2) | 0.017 (2) | 0.004 (2) |
C5 | 0.060 (2) | 0.059 (2) | 0.0632 (19) | −0.0004 (17) | 0.0177 (16) | 0.0039 (16) |
C6 | 0.054 (2) | 0.056 (2) | 0.0446 (17) | 0.0002 (16) | 0.0118 (14) | −0.0012 (15) |
C7 | 0.057 (2) | 0.055 (2) | 0.0436 (17) | 0.0067 (16) | 0.0129 (15) | −0.0004 (14) |
C8 | 0.059 (2) | 0.054 (2) | 0.0539 (18) | 0.0068 (16) | 0.0236 (15) | −0.0034 (15) |
C9 | 0.056 (2) | 0.052 (2) | 0.0485 (18) | 0.0103 (15) | 0.0083 (16) | −0.0064 (15) |
C10 | 0.076 (3) | 0.052 (2) | 0.079 (2) | 0.0032 (18) | 0.020 (2) | −0.0127 (18) |
C11 | 0.0494 (16) | 0.0426 (19) | 0.0555 (16) | −0.0036 (15) | 0.0068 (13) | −0.0035 (14) |
C12 | 0.058 (2) | 0.066 (2) | 0.062 (2) | 0.0052 (18) | 0.0017 (16) | 0.0059 (17) |
C13 | 0.0471 (18) | 0.077 (3) | 0.086 (2) | 0.0031 (19) | 0.0085 (16) | 0.006 (2) |
C14 | 0.0492 (17) | 0.067 (2) | 0.080 (2) | 0.001 (2) | 0.0154 (15) | 0.006 (2) |
C15 | 0.054 (2) | 0.055 (2) | 0.067 (2) | 0.0028 (16) | 0.0117 (16) | 0.0074 (16) |
C16 | 0.0427 (15) | 0.0422 (17) | 0.0554 (16) | −0.0017 (16) | 0.0072 (12) | −0.0009 (16) |
C17 | 0.0346 (16) | 0.049 (2) | 0.067 (2) | −0.0084 (14) | −0.0023 (14) | −0.0025 (15) |
C18 | 0.051 (2) | 0.0446 (18) | 0.0539 (18) | −0.0047 (14) | 0.0007 (15) | 0.0012 (14) |
C19 | 0.059 (2) | 0.044 (2) | 0.100 (3) | −0.0091 (16) | −0.0043 (19) | −0.0098 (19) |
N1 | 0.0599 (17) | 0.0355 (16) | 0.0570 (16) | 0.0022 (13) | 0.0159 (13) | −0.0019 (12) |
N2 | 0.0423 (15) | 0.0394 (16) | 0.0593 (15) | −0.0008 (12) | 0.0016 (12) | −0.0015 (12) |
O1 | 0.0683 (14) | 0.0472 (12) | 0.0774 (14) | 0.0002 (11) | 0.0368 (12) | −0.0076 (11) |
Mn1 | 0.0409 (2) | 0.0408 (2) | 0.0614 (3) | −0.0036 (2) | 0.01121 (18) | −0.0069 (2) |
Cl1 | 0.0547 (5) | 0.0699 (6) | 0.0698 (5) | 0.0008 (4) | 0.0009 (4) | 0.0060 (4) |
Cl2 | 0.0595 (5) | 0.0609 (5) | 0.0653 (5) | 0.0011 (4) | 0.0170 (4) | 0.0038 (4) |
C21 | 0.0376 (17) | 0.0477 (18) | 0.0491 (17) | −0.0019 (14) | 0.0035 (13) | −0.0011 (14) |
C20 | 0.0412 (17) | 0.0507 (19) | 0.0497 (17) | −0.0070 (14) | 0.0038 (13) | −0.0020 (14) |
O2 | 0.0372 (11) | 0.0454 (13) | 0.0959 (15) | −0.0056 (10) | −0.0021 (10) | −0.0128 (11) |
C24 | 0.046 (2) | 0.066 (3) | 0.077 (2) | 0.0108 (18) | 0.0070 (17) | −0.0047 (19) |
C25 | 0.058 (2) | 0.053 (2) | 0.083 (2) | 0.0041 (18) | 0.0060 (18) | 0.0072 (18) |
C23 | 0.0420 (19) | 0.077 (3) | 0.088 (2) | −0.0017 (17) | 0.0166 (17) | 0.0029 (19) |
C22 | 0.0449 (19) | 0.053 (2) | 0.077 (2) | −0.0020 (16) | 0.0126 (16) | 0.0050 (17) |
C26 | 0.0415 (18) | 0.054 (2) | 0.072 (2) | −0.0025 (15) | 0.0055 (15) | 0.0062 (15) |
Geometric parameters (Å, º) top
C1—C2 | 1.380 (5) | C15—C16 | 1.524 (4) |
C1—C6 | 1.386 (5) | C15—H15A | 0.9700 |
C1—H1 | 0.9300 | C15—H15B | 0.9700 |
C2—C3 | 1.359 (5) | C16—N2 | 1.465 (3) |
C2—H2 | 0.9300 | C16—H16 | 0.9800 |
C3—C4 | 1.378 (5) | C17—C20 | 1.374 (4) |
C3—H3 | 0.9300 | C17—C18 | 1.404 (4) |
C4—C5 | 1.381 (5) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—N2 | 1.323 (4) |
C5—C6 | 1.384 (4) | C18—C19 | 1.497 (4) |
C5—H5 | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.494 (4) | C19—H19B | 0.9600 |
C7—O1 | 1.289 (3) | C19—H19C | 0.9600 |
C7—C8 | 1.382 (4) | N1—H1A | 0.83 (3) |
C8—C9 | 1.415 (4) | N2—H2A | 0.95 (4) |
C8—H8 | 0.9300 | O1—Mn1 | 2.031 (2) |
C9—N1 | 1.308 (4) | Mn1—O2i | 2.0192 (19) |
C9—C10 | 1.502 (4) | Mn1—Cl2 | 2.3298 (10) |
C10—H10A | 0.9600 | Mn1—Cl1 | 2.3301 (10) |
C10—H10B | 0.9600 | C21—C26 | 1.385 (4) |
C10—H10C | 0.9600 | C21—C22 | 1.394 (4) |
C11—N1 | 1.465 (4) | C21—C20 | 1.490 (4) |
C11—C12 | 1.520 (4) | C20—O2 | 1.291 (3) |
C11—C16 | 1.538 (4) | O2—Mn1ii | 2.0192 (19) |
C11—H11 | 0.9800 | C24—C23 | 1.365 (5) |
C12—C13 | 1.524 (4) | C24—C25 | 1.368 (5) |
C12—H12A | 0.9700 | C24—H24 | 0.9300 |
C12—H12B | 0.9700 | C25—C26 | 1.379 (4) |
C13—C14 | 1.519 (4) | C25—H25 | 0.9300 |
C13—H13A | 0.9700 | C23—C22 | 1.384 (5) |
C13—H13B | 0.9700 | C23—H23 | 0.9300 |
C14—C15 | 1.531 (4) | C22—H22 | 0.9300 |
C14—H14A | 0.9700 | C26—H26 | 0.9300 |
C14—H14B | 0.9700 | | |
| | | |
C2—C1—C6 | 120.6 (4) | C16—C15—H15A | 109.5 |
C2—C1—H1 | 119.7 | C14—C15—H15A | 109.5 |
C6—C1—H1 | 119.7 | C16—C15—H15B | 109.5 |
C3—C2—C1 | 120.9 (4) | C14—C15—H15B | 109.5 |
C3—C2—H2 | 119.6 | H15A—C15—H15B | 108.1 |
C1—C2—H2 | 119.6 | N2—C16—C15 | 109.2 (3) |
C2—C3—C4 | 119.4 (4) | N2—C16—C11 | 110.0 (2) |
C2—C3—H3 | 120.3 | C15—C16—C11 | 111.1 (2) |
C4—C3—H3 | 120.3 | N2—C16—H16 | 108.8 |
C3—C4—C5 | 120.2 (4) | C15—C16—H16 | 108.8 |
C3—C4—H4 | 119.9 | C11—C16—H16 | 108.8 |
C5—C4—H4 | 119.9 | C20—C17—C18 | 125.7 (3) |
C4—C5—C6 | 120.7 (4) | C20—C17—H17 | 117.2 |
C4—C5—H5 | 119.6 | C18—C17—H17 | 117.2 |
C6—C5—H5 | 119.6 | N2—C18—C17 | 120.9 (3) |
C5—C6—C1 | 118.2 (3) | N2—C18—C19 | 119.5 (3) |
C5—C6—C7 | 120.0 (3) | C17—C18—C19 | 119.6 (3) |
C1—C6—C7 | 121.8 (3) | C18—C19—H19A | 109.5 |
O1—C7—C8 | 121.6 (3) | C18—C19—H19B | 109.5 |
O1—C7—C6 | 117.3 (3) | H19A—C19—H19B | 109.5 |
C8—C7—C6 | 121.0 (3) | C18—C19—H19C | 109.5 |
C7—C8—C9 | 124.0 (3) | H19A—C19—H19C | 109.5 |
C7—C8—H8 | 118.0 | H19B—C19—H19C | 109.5 |
C9—C8—H8 | 118.0 | C9—N1—C11 | 131.5 (3) |
N1—C9—C8 | 121.9 (3) | C9—N1—H1A | 113.7 (19) |
N1—C9—C10 | 120.5 (3) | C11—N1—H1A | 114.8 (19) |
C8—C9—C10 | 117.6 (3) | C18—N2—C16 | 129.6 (3) |
C9—C10—H10A | 109.5 | C18—N2—H2A | 119 (2) |
C9—C10—H10B | 109.5 | C16—N2—H2A | 111 (2) |
H10A—C10—H10B | 109.5 | C7—O1—Mn1 | 151.7 (2) |
C9—C10—H10C | 109.5 | O2i—Mn1—O1 | 117.68 (9) |
H10A—C10—H10C | 109.5 | O2i—Mn1—Cl2 | 108.93 (7) |
H10B—C10—H10C | 109.5 | O1—Mn1—Cl2 | 101.38 (7) |
N1—C11—C12 | 109.1 (3) | O2i—Mn1—Cl1 | 99.88 (7) |
N1—C11—C16 | 109.9 (2) | O1—Mn1—Cl1 | 108.22 (7) |
C12—C11—C16 | 110.8 (2) | Cl2—Mn1—Cl1 | 121.82 (4) |
N1—C11—H11 | 109.0 | C26—C21—C22 | 118.3 (3) |
C12—C11—H11 | 109.0 | C26—C21—C20 | 120.0 (3) |
C16—C11—H11 | 109.0 | C22—C21—C20 | 121.7 (3) |
C11—C12—C13 | 112.3 (3) | O2—C20—C17 | 120.4 (3) |
C11—C12—H12A | 109.1 | O2—C20—C21 | 117.9 (3) |
C13—C12—H12A | 109.1 | C17—C20—C21 | 121.6 (3) |
C11—C12—H12B | 109.1 | C20—O2—Mn1ii | 152.3 (2) |
C13—C12—H12B | 109.1 | C23—C24—C25 | 119.9 (4) |
H12A—C12—H12B | 107.9 | C23—C24—H24 | 120.0 |
C14—C13—C12 | 110.7 (3) | C25—C24—H24 | 120.0 |
C14—C13—H13A | 109.5 | C24—C25—C26 | 120.9 (3) |
C12—C13—H13A | 109.5 | C24—C25—H25 | 119.6 |
C14—C13—H13B | 109.5 | C26—C25—H25 | 119.6 |
C12—C13—H13B | 109.5 | C24—C23—C22 | 120.0 (3) |
H13A—C13—H13B | 108.1 | C24—C23—H23 | 120.0 |
C13—C14—C15 | 110.1 (3) | C22—C23—H23 | 120.0 |
C13—C14—H14A | 109.6 | C23—C22—C21 | 120.7 (3) |
C15—C14—H14A | 109.6 | C23—C22—H22 | 119.6 |
C13—C14—H14B | 109.6 | C21—C22—H22 | 119.6 |
C15—C14—H14B | 109.6 | C25—C26—C21 | 120.2 (3) |
H14A—C14—H14B | 108.2 | C25—C26—H26 | 119.9 |
C16—C15—C14 | 110.9 (3) | C21—C26—H26 | 119.9 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.95 (4) | 1.92 (3) | 2.635 (3) | 130 (3) |
N1—H1A···O1 | 0.83 (3) | 1.95 (3) | 2.641 (4) | 140 (2) |
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