A one-dimensional coordination polymer formed from the reaction of 1,1-diphenyl-3,3′-[(1R,2R)-cyclo­hexane-1,2-diylbis(aza­nedi­yl)]dibut-2-en-1-one with MnCl₂·4H₂O

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 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.

Computing details

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']

Crystal data

[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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0278P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—O2^i	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—Mn1^ii	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	O2^i—Mn1—O1	117.68 (9)
H10A—C10—H10C	109.5	O2^i—Mn1—Cl2	108.93 (7)
H10B—C10—H10C	109.5	O1—Mn1—Cl2	101.38 (7)
N1—C11—C12	109.1 (3)	O2^i—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—Mn1^ii	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)

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)