Bis(tetra-n-butyl­ammonium) tetra­bromo­cadmate(II) toluene disolvate

Kropidłowska, A.; Chojnacki, J.; Becker, B.

doi:10.1107/S1600536806003916

Bis(tetra-n-butylammonium) tetrabromocadmate(II) toluene disolvate

A. Kropidlowska, J. Chojnacki and B. Becker

The title compound, (C₁₆H₃₆N)₂[CdBr₄]·2C₇H₈, consists of a [CdBr₄]^2- anion possessing $\overline{4}$ crystallographic symmetry and two tetra-n-butylammonium cations of twofold symmetry accompanied by two toluene molecules disordered around a twofold axis. The anion is enclosed within a cage formed of four cations and four solvent molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003916/br6225sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003916/br6225Isup2.hkl Contains datablock I

CCDC reference: 601114

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R factor = 0.041
wR factor = 0.095
Data-to-parameter ratio = 29.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          1
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.20
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       8.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C12    ...       1.37 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               3926
           Count of symmetry unique reflns         2147
           Completeness (_total/calc)            182.86%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1779
           Fraction of Friedel pairs measured     0.829
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005).; cell refinement: CrysAlis RED (Oxford Diffraction, 2005).; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(tetra-n-butylammonium) tetrabromocadmate(II) toluene disolvate top

Crystal data top

(C₁₆H₃₆N)₂[CdBr₄]·2C₇H₈	D_x = 1.362 Mg m⁻³
M_r = 1101.22	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I42d	Cell parameters from 13314 reflections
Hall symbol: I -4 2bw	θ = 2.8–32.6°
a = 15.1535 (9) Å	µ = 3.41 mm⁻¹
c = 23.3816 (18) Å	T = 100 K
V = 5369.1 (6) Å³	Block, colourless
Z = 4	0.20 × 0.16 × 0.11 mm
F(000) = 2264

Data collection top

Goniometer: KUMA KM4, detector: Sapphire-2 CCD, Oxford Diffraction Ltd diffractometer	3926 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 30°, θ_min = 2.9°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2005) based on Clark & Reid (1998)]	h = −21→20
T_min = 0.403, T_max = 0.476	k = −21→15
18127 measured reflections	l = −32→32

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0454P)² + 17.459P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.004
3926 reflections	Δρ_max = 1.19 e Å⁻³
132 parameters	Δρ_min = −0.72 e Å⁻³
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.021 (10)

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	U_iso*/U_eq	Occ. (<1)
Br2	−0.12584 (2)	0.05906 (2)	0.064459 (14)	0.02373 (9)
Cd1	0	0	0	0.02038 (10)
C1	0.0487 (2)	0.2470 (3)	0.07172 (13)	0.0238 (6)
H1A	0.0881	0.2465	0.038	0.029*
H1B	0.0157	0.1906	0.0717	0.029*
C2	−0.0158 (3)	0.3205 (3)	0.06474 (18)	0.0388 (10)
H2A	0.0169	0.3769	0.0625	0.047*
H2B	−0.0541	0.3229	0.099	0.047*
C3	−0.0731 (3)	0.3112 (3)	0.01218 (15)	0.0301 (8)
H3A	−0.0353	0.3142	−0.0223	0.036*
H3B	−0.1017	0.2525	0.0127	0.036*
C4	−0.1437 (4)	0.3814 (5)	0.0079 (2)	0.0606 (17)
H4A	−0.1845	0.3757	0.0402	0.073*
H4B	−0.1762	0.374	−0.028	0.073*
H4C	−0.1161	0.4399	0.0087	0.073*
C5	0.1619 (2)	0.1675 (2)	0.12446 (15)	0.0229 (6)
H5A	0.1954	0.1659	0.0881	0.027*
H5B	0.1223	0.1155	0.1248	0.027*
C6	0.2267 (3)	0.1587 (3)	0.17362 (18)	0.0357 (9)
H6A	0.2631	0.2129	0.176	0.043*
H6B	0.1937	0.1527	0.21	0.043*
C7	0.2864 (3)	0.0795 (3)	0.16591 (17)	0.0331 (8)
H7A	0.3192	0.0858	0.1295	0.04*
H7B	0.2497	0.0256	0.1632	0.04*
C8	0.3519 (4)	0.0686 (4)	0.2144 (2)	0.0489 (12)
H8A	0.3907	0.1203	0.216	0.059*
H8B	0.3873	0.0155	0.208	0.059*
H8C	0.3199	0.0631	0.2507	0.059*
N1	0.1055 (3)	0.25	0.125	0.0203 (7)
C9	0.5197 (4)	0.25	0.125	0.0387 (13)
H9	0.4571	0.25	0.125	0.046*
C10	0.5673 (5)	0.1731 (4)	0.1116 (2)	0.0531 (14)
C11	0.5404 (8)	0.0832 (7)	0.0955 (5)	0.055 (3)	0.5
H11A	0.5723	0.0651	0.061	0.066*	0.5
H11B	0.4768	0.0822	0.088	0.066*	0.5
H11C	0.5542	0.0425	0.1268	0.066*	0.5
C12	0.6573 (5)	0.1759 (6)	0.1123 (3)	0.086 (3)
H12	0.69	0.1241	0.1036	0.103*
C13	0.6995 (7)	0.25	0.125	0.107 (5)
H13	0.7622	0.25	0.125	0.129*
H10	0.5354 (12)	0.1213 (14)	0.102 (2)	0.129*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.02382 (17)	0.02792 (18)	0.01944 (14)	−0.00373 (13)	0.00331 (12)	−0.00470 (12)
Cd1	0.02256 (14)	0.02256 (14)	0.01603 (18)	0	0	0
C1	0.0299 (17)	0.0275 (16)	0.0140 (13)	0.0041 (14)	0.0022 (11)	−0.0040 (12)
C2	0.049 (3)	0.039 (2)	0.0275 (17)	0.0181 (19)	−0.0162 (18)	−0.0134 (16)
C3	0.036 (2)	0.0316 (19)	0.0230 (16)	0.0027 (17)	−0.0049 (14)	0.0009 (14)
C4	0.068 (4)	0.073 (4)	0.042 (3)	0.039 (3)	−0.015 (2)	−0.014 (3)
C5	0.0291 (17)	0.0203 (15)	0.0192 (14)	0.0008 (13)	−0.0021 (12)	−0.0028 (12)
C6	0.044 (2)	0.033 (2)	0.0299 (19)	0.0103 (17)	−0.0108 (16)	−0.0083 (15)
C7	0.034 (2)	0.035 (2)	0.0303 (18)	0.0051 (16)	−0.0071 (15)	0.0033 (15)
C8	0.050 (3)	0.054 (3)	0.042 (2)	0.014 (2)	−0.014 (2)	0.010 (2)
N1	0.0210 (19)	0.0229 (19)	0.0172 (16)	0	0	−0.0033 (14)
C9	0.034 (3)	0.048 (3)	0.035 (3)	0	0	0.010 (3)
C10	0.083 (4)	0.041 (3)	0.035 (2)	−0.001 (3)	−0.008 (2)	−0.0009 (19)
C11	0.053 (6)	0.046 (6)	0.067 (7)	0.011 (5)	−0.011 (5)	−0.013 (5)
C12	0.070 (5)	0.110 (7)	0.078 (5)	0.056 (5)	0.019 (4)	0.027 (5)
C13	0.035 (5)	0.146 (14)	0.141 (13)	0	0	0.057 (11)

Geometric parameters (Å, º) top

Br2—Cd1	2.5901 (4)	C6—H6B	0.99
Cd1—Br2ⁱ	2.5901 (3)	C7—C8	1.516 (6)
Cd1—Br2ⁱⁱ	2.5901 (4)	C7—H7A	0.99
Cd1—Br2ⁱⁱⁱ	2.5901 (4)	C7—H7B	0.99
C1—C2	1.491 (5)	C8—H8A	0.98
C1—N1	1.515 (4)	C8—H8B	0.98
C1—H1A	0.99	C8—H8C	0.98
C1—H1B	0.99	N1—C1^iv	1.515 (4)
C2—C3	1.512 (5)	N1—C5^iv	1.515 (4)
C2—H2A	0.99	C9—C10^iv	1.405 (7)
C2—H2B	0.99	C9—C10	1.405 (7)
C3—C4	1.511 (6)	C9—H9	0.95
C3—H3A	0.99	C10—C12	1.364 (10)
C3—H3B	0.99	C10—C11	1.471 (12)
C4—H4A	0.98	C10—H10	0.949 (10)
C4—H4B	0.98	C11—H11A	0.98
C4—H4C	0.98	C11—H11B	0.98
C5—N1	1.515 (4)	C11—H11C	0.98
C5—C6	1.518 (5)	C11—H10	0.601 (19)
C5—H5A	0.99	C12—C13	1.326 (11)
C5—H5B	0.99	C12—H12	0.95
C6—C7	1.514 (6)	C13—C12^iv	1.326 (11)
C6—H6A	0.99	C13—H13	0.95

Br2ⁱ—Cd1—Br2ⁱⁱ	109.791 (8)	C6—C7—C8	112.8 (4)
Br2ⁱ—Cd1—Br2	108.833 (16)	C6—C7—H7A	109
Br2ⁱⁱ—Cd1—Br2	109.791 (8)	C8—C7—H7A	109
Br2ⁱ—Cd1—Br2ⁱⁱⁱ	109.791 (8)	C6—C7—H7B	109
Br2ⁱⁱ—Cd1—Br2ⁱⁱⁱ	108.833 (16)	C8—C7—H7B	109
Br2—Cd1—Br2ⁱⁱⁱ	109.791 (8)	H7A—C7—H7B	107.8
C2—C1—N1	116.1 (3)	C7—C8—H8A	109.5
C2—C1—H1A	108.3	C7—C8—H8B	109.5
N1—C1—H1A	108.3	H8A—C8—H8B	109.5
C2—C1—H1B	108.3	C7—C8—H8C	109.5
N1—C1—H1B	108.3	H8A—C8—H8C	109.5
H1A—C1—H1B	107.4	H8B—C8—H8C	109.5
C1—C2—C3	113.4 (3)	C1—N1—C1^iv	110.8 (4)
C1—C2—H2A	108.9	C1—N1—C5^iv	110.6 (2)
C3—C2—H2A	108.9	C1^iv—N1—C5^iv	106.76 (19)
C1—C2—H2B	108.9	C1—N1—C5	106.76 (19)
C3—C2—H2B	108.9	C1^iv—N1—C5	110.6 (2)
H2A—C2—H2B	107.7	C5^iv—N1—C5	111.3 (4)
C4—C3—C2	113.3 (4)	C10^iv—C9—C10	118.3 (7)
C4—C3—H3A	108.9	C10^iv—C9—H9	120.8
C2—C3—H3A	108.9	C10—C9—H9	120.8
C4—C3—H3B	108.9	C12—C10—C9	119.0 (6)
C2—C3—H3B	108.9	C12—C10—C11	108.0 (8)
H3A—C3—H3B	107.7	C9—C10—C11	133.1 (8)
C3—C4—H4A	109.5	C12—C10—H10	122.5 (12)
C3—C4—H4B	109.5	C9—C10—H10	118.6 (13)
H4A—C4—H4B	109.5	C10—C11—H11A	109.5
C3—C4—H4C	109.5	C10—C11—H11B	109.5
H4A—C4—H4C	109.5	H11A—C11—H11B	109.5
H4B—C4—H4C	109.5	C10—C11—H11C	109.5
N1—C5—C6	115.5 (3)	H11A—C11—H11C	109.5
N1—C5—H5A	108.4	H11B—C11—H11C	109.5
C6—C5—H5A	108.4	H11A—C11—H10	122.5
N1—C5—H5B	108.4	H11B—C11—H10	86.4
C6—C5—H5B	108.4	H11C—C11—H10	116.4
H5A—C5—H5B	107.5	C13—C12—C10	120.7 (8)
C7—C6—C5	111.5 (3)	C13—C12—H12	119.6
C7—C6—H6A	109.3	C10—C12—H12	119.6
C5—C6—H6A	109.3	C12—C13—C12^iv	122.3 (10)
C7—C6—H6B	109.3	C12—C13—H13	118.9
C5—C6—H6B	109.3	C12^iv—C13—H13	118.9
H6A—C6—H6B	108

Symmetry codes: (i) −x, −y, z; (ii) −y, x, −z; (iii) y, −x, −z; (iv) x, −y+1/2, −z+1/4.

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Bis(tetra-n-butyl­ammonium) tetra­bromo­cadmate(II) toluene disolvate

Supporting information

Key indicators

checkCIF/PLATON results

Bis(tetra-n-butylammonium) tetrabromocadmate(II) toluene disolvate