catena-Poly­[[di­bromo­zinc(II)]-μ-(R,R)-1,2-diacet­amido­cyclo­hexane]

The asymmetric unit of the title compound, [ZnBr₂(C₁₀H₁₈N₂O₂)], contains a fragment of the polymeric chain [(R,R)-1,2-diacet­amido­cyclo­hexane­di­bromo­zinc(II)]_n. The Zn atom is coordinated by two bromide anions and two 1,2-diacet­amido­cyclo­hexane (DCH) ligands acting as 1,8-bridging via the O atoms. The complex exhibits a distorted tetrahedral geometry around the Zn atom. The crystal packing is characterized by several van der Waals contacts, these interactions resulting in chains parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.031
• wR factor = 0.076
• Data-to-parameter ratio = 15.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N10    -   H10    ...          ?

PLAT_712  Alert C ANGLE   Unknown or Inconsistent Label ..........        ZN1
                           C11    O11    ZN1

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.98
         From the CIF: _reflns_number_total               2335
         Count of symmetry unique reflns         2338
         Completeness (_total/calc)             99.87%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Version 1.63.02; Farrugia, 1999).

catena-Poly[dibromozinc(II)]-µ-(R,R)-1,2-diacetamidocyclohexane]

Crystal data

[ZnBr2(C10H18N2O2)]	Dx = 1.791 Mg m^−3 Dm = 1.78 (2) Mg m^−3 Dm measured by flotation in CCl4 and C2H4Br2
Mr = 423.45	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 25 reflections
Hall symbol: P 4cw	θ = 6.5–9.9°
a = 7.496 (2) Å	µ = 6.65 mm^−1
c = 27.941 (5) Å	T = 293 K
V = 1570.0 (7) Å^3	Parallelepiped, colourless
Z = 4	0.40 × 0.38 × 0.28 mm
F(000) = 832

Data collection

Enraf–Nonius CAD-4 diffractometer	1330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 30.0°, θmin = 2.7°
ω–2θ scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = 0→10
Tmin = 0.086, Tmax = 0.159	l = 0→39
4956 measured reflections	3 standard reflections every 1 min
2335 independent reflections	intensity decay: 1%

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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0339P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
2335 reflections	Δρmax = 0.32 e Å^−3
155 parameters	Δρmin = −0.62 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.015 (15)

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
Zn	0.46447 (8)	0.59027 (7)	0.10001 (2)	0.04035 (15)
Br1	0.76449 (8)	0.67589 (10)	0.10419 (3)	0.0628 (2)
Br2	0.28072 (10)	0.64166 (12)	0.16672 (3)	0.0732 (2)
O2	0.4092 (6)	1.3516 (5)	0.07407 (16)	0.0531 (11)
C2	0.3939 (8)	1.2039 (7)	0.09339 (19)	0.0415 (14)
N3	0.2741 (7)	1.0892 (6)	0.07562 (17)	0.0430 (11)
H3	0.2697	0.9837	0.0876	0.087 (6)*
C1	0.5041 (11)	1.1457 (9)	0.1345 (3)	0.0646 (19)
H11	0.5029	1.0179	0.1365	0.087 (6)*
H12	0.4563	1.1951	0.1635	0.087 (6)*
H13	0.6244	1.1865	0.1302	0.087 (6)*
C4	0.1507 (7)	1.1333 (7)	0.0370 (2)	0.0429 (12)
H4	0.2092	1.2174	0.0152	0.087 (6)*
C5	−0.0163 (10)	1.2213 (10)	0.0575 (3)	0.0691 (19)
H51	−0.0715	1.1421	0.0806	0.087 (6)*
H52	0.0162	1.3307	0.0738	0.087 (6)*
C6	−0.1470 (11)	1.2622 (12)	0.0179 (3)	0.084 (3)
H61	−0.2531	1.3164	0.0314	0.087 (6)*
H62	−0.0938	1.3470	−0.0041	0.087 (6)*
C7	−0.1980 (11)	1.0963 (12)	−0.0088 (3)	0.081 (2)
H71	−0.2791	1.1270	−0.0346	0.087 (6)*
H72	−0.2595	1.0153	0.0127	0.087 (6)*
C8	−0.0331 (9)	1.0034 (11)	−0.0295 (3)	0.0604 (18)
H81	−0.0687	0.8925	−0.0447	0.087 (6)*
H82	0.0203	1.0790	−0.0538	0.087 (6)*
C9	0.1040 (8)	0.9645 (7)	0.0093 (2)	0.0416 (13)
H9	0.0533	0.8773	0.0316	0.087 (6)*
N10	0.2617 (6)	0.8851 (6)	−0.01365 (18)	0.0449 (11)
H10	0.2864	0.9164	−0.0425	0.087 (6)*
C12	0.5190 (9)	0.6932 (10)	−0.0194 (3)	0.0638 (18)
H121	0.5204	0.7424	−0.0511	0.087 (6)*
H122	0.5066	0.5659	−0.0212	0.087 (6)*
H123	0.6286	0.7222	−0.0034	0.087 (6)*
C11	0.3679 (7)	0.7683 (7)	0.0076 (2)	0.0402 (13)
O11	0.3348 (6)	0.7240 (5)	0.05029 (16)	0.0509 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0461 (3)	0.0310 (3)	0.0440 (3)	0.0021 (3)	−0.0011 (3)	0.0009 (3)
Br1	0.0494 (3)	0.0751 (4)	0.0640 (4)	−0.0129 (3)	−0.0024 (3)	−0.0017 (4)
Br2	0.0617 (4)	0.1008 (6)	0.0572 (4)	0.0182 (4)	0.0131 (4)	−0.0070 (4)
O2	0.072 (3)	0.034 (2)	0.054 (3)	−0.0114 (19)	0.001 (2)	−0.0018 (18)
C2	0.053 (3)	0.028 (2)	0.043 (4)	0.001 (2)	0.006 (3)	−0.008 (2)
N3	0.061 (3)	0.024 (2)	0.044 (3)	0.001 (2)	−0.001 (2)	−0.0004 (19)
C1	0.089 (5)	0.048 (4)	0.056 (4)	0.004 (4)	−0.020 (4)	−0.008 (3)
C4	0.047 (3)	0.034 (3)	0.048 (3)	0.004 (2)	0.000 (3)	0.001 (2)
C5	0.064 (4)	0.071 (5)	0.073 (5)	0.026 (4)	0.010 (4)	0.000 (4)
C6	0.062 (4)	0.080 (6)	0.109 (7)	0.024 (4)	−0.003 (5)	0.009 (5)
C7	0.060 (5)	0.093 (6)	0.090 (7)	0.002 (4)	−0.016 (4)	0.014 (5)
C8	0.050 (4)	0.063 (4)	0.069 (5)	0.005 (3)	−0.018 (3)	0.002 (3)
C9	0.046 (3)	0.037 (3)	0.042 (3)	−0.002 (2)	0.001 (2)	0.005 (2)
N10	0.053 (3)	0.044 (2)	0.038 (3)	0.005 (2)	−0.003 (2)	0.004 (2)
C12	0.061 (4)	0.068 (4)	0.063 (4)	0.018 (3)	−0.010 (3)	−0.020 (4)
C11	0.042 (3)	0.035 (3)	0.044 (3)	0.002 (2)	−0.007 (2)	−0.008 (2)
O11	0.059 (3)	0.042 (2)	0.051 (3)	0.0040 (19)	−0.007 (2)	0.0152 (19)

Geometric parameters (Å, º)

Zn—O11	1.970 (4)	C6—C7	1.500 (12)
Zn—O2^i	1.974 (4)	C6—H61	0.9700
Zn—Br1	2.3416 (11)	C6—H62	0.9700
Zn—Br2	2.3495 (10)	C7—C8	1.532 (11)
Zn—Zn^ii	7.496 (2)	C7—H71	0.9700
O2—C2	1.237 (7)	C7—H72	0.9700
C2—N3	1.339 (7)	C8—C9	1.522 (8)
C2—C1	1.480 (9)	C8—H81	0.9700
N3—C4	1.460 (7)	C8—H82	0.9700
N3—H3	0.8600	C9—N10	1.470 (8)
C1—H11	0.9600	C9—H9	0.9800
C1—H12	0.9600	N10—C11	1.324 (7)
C1—H13	0.9600	N10—H10	0.8600
C4—C5	1.527 (8)	C12—C11	1.472 (8)
C4—C9	1.524 (8)	C12—H121	0.9600
C4—H4	0.9800	C12—H122	0.9600
C5—C6	1.509 (11)	C12—H123	0.9600
C5—H51	0.9700	C11—O11	1.264 (7)
C5—H52	0.9700
O11—Zn—O2^i	95.67 (18)	C7—C6—H61	109.4
O11—Zn—Br1	111.69 (13)	C5—C6—H61	109.4
O2^i—Zn—Br1	117.92 (14)	C7—C6—H62	109.4
O11—Zn—Br2	100.76 (14)	C5—C6—H62	109.4
O2^i—Zn—Br2	108.47 (14)	H61—C6—H62	108.0
Br1—Zn—Br2	118.59 (4)	C6—C7—C8	111.0 (7)
O11—Zn—Zn^ii	59.41 (13)	C6—C7—H71	109.4
O2^i—Zn—Zn^ii	154.99 (13)	C8—C7—H71	109.4
Br1—Zn—Zn^ii	74.09 (2)	C6—C7—H72	109.4
Br2—Zn—Zn^ii	80.56 (3)	C8—C7—H72	109.4
C2—O2—Zn^ii	132.1 (4)	H71—C7—H72	108.0
O2—C2—N3	118.4 (5)	C9—C8—C7	111.3 (6)
O2—C2—C1	123.4 (5)	C9—C8—H81	109.4
N3—C2—C1	118.2 (5)	C7—C8—H81	109.4
C2—N3—C4	123.6 (4)	C9—C8—H82	109.4
C2—N3—H3	118.2	C7—C8—H82	109.4
C4—N3—H3	118.2	H81—C8—H82	108.0
C2—C1—H11	109.5	N10—C9—C8	108.1 (5)
C2—C1—H12	109.5	N10—C9—C4	111.9 (5)
H11—C1—H12	109.5	C8—C9—C4	111.0 (5)
C2—C1—H13	109.5	N10—C9—H9	108.6
H11—C1—H13	109.5	C8—C9—H9	108.6
H12—C1—H13	109.5	C4—C9—H9	108.6
N3—C4—C5	109.8 (5)	C11—N10—C9	123.8 (5)
N3—C4—C9	109.5 (4)	C11—N10—H10	118.1
C5—C4—C9	111.2 (5)	C9—N10—H10	118.1
N3—C4—H4	108.8	C11—C12—H121	109.5
C5—C4—H4	108.8	C11—C12—H122	109.5
C9—C4—H4	108.8	H121—C12—H122	109.5
C6—C5—C4	110.1 (6)	C11—C12—H123	109.5
C6—C5—H51	109.6	H121—C12—H123	109.5
C4—C5—H51	109.6	H122—C12—H123	109.5
C6—C5—H52	109.6	O11—C11—N10	118.6 (5)
C4—C5—H52	109.6	O11—C11—C12	122.3 (6)
H51—C5—H52	108.1	N10—C11—C12	119.1 (6)
C7—C6—C5	111.2 (6)	C11—O11—Zn1	134.7 (4)

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
N3—H3···O11	0.86	2.26	2.864 (6)	127