Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003916/br6225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003916/br6225Isup2.hkl |
CCDC reference: 601114
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
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).
(C16H36N)2[CdBr4]·2C7H8 | Dx = 1.362 Mg m−3 |
Mr = 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 |
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 | Rint = 0.054 |
ω scans | θmax = 30°, θmin = 2.9° |
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2005) based on Clark & Reid (1998)] | h = −21→20 |
Tmin = 0.403, Tmax = 0.476 | k = −21→15 |
18127 measured reflections | l = −32→32 |
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(Fo2) + (0.0454P)2 + 17.459P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.004 |
3926 reflections | Δρmax = 1.19 e Å−3 |
132 parameters | Δρmin = −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) |
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. |
x | y | z | Uiso*/Ueq | 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 |
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) |
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—C1iv | 1.515 (4) |
C2—C3 | 1.512 (5) | N1—C5iv | 1.515 (4) |
C2—H2A | 0.99 | C9—C10iv | 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—C12iv | 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—C1iv | 110.8 (4) |
C1—C2—H2A | 108.9 | C1—N1—C5iv | 110.6 (2) |
C3—C2—H2A | 108.9 | C1iv—N1—C5iv | 106.76 (19) |
C1—C2—H2B | 108.9 | C1—N1—C5 | 106.76 (19) |
C3—C2—H2B | 108.9 | C1iv—N1—C5 | 110.6 (2) |
H2A—C2—H2B | 107.7 | C5iv—N1—C5 | 111.3 (4) |
C4—C3—C2 | 113.3 (4) | C10iv—C9—C10 | 118.3 (7) |
C4—C3—H3A | 108.9 | C10iv—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—C12iv | 122.3 (10) |
C7—C6—H6B | 109.3 | C12—C13—H13 | 118.9 |
C5—C6—H6B | 109.3 | C12iv—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. |