In the first title compound, [Au(C
7H
11BrN
2)
2]I, the cations and anions form chains
via halogen bond linkages Br

I

Br. The second title compound, [Au(C
7H
11BrN
2)
2][AuI
2(C
7H
11BrN
2)
2]I
2, forms a layer structure involving Br

I

Br and I

I

Au linkages.
Supporting information
CCDC references: 2119423; 2119422
Key indicators
Structure: 3
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.023
- wR factor = 0.052
- Data-to-parameter ratio = 46.2
Structure: 4
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.011 Å
- R factor = 0.039
- wR factor = 0.105
- Data-to-parameter ratio = 29.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 ..I1 . 3.15 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A ..I1 . 3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A ..I1 . 3.21 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 ..I1 . 3.20 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B ..I1 . 3.19 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B ..BR1 . 3.06 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B ..I1 . 3.19 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
PLAT972_ALERT_2_C Check Calcd Resid. Dens. 0.30A From I1 -1.88 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens. 0.30A From I1 -1.88 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens. 0.43A From I1 -1.78 eA-3
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C14 H22 Au1 Br2 I1 N4
Atom count from _chemical_formula_moiety:
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ Please Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact I1 ..Br1 3.53 Ang.
-1+x,-1+y,1+z = 1_446 Check
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note
I
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 631 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
9 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
10 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Alert level A
PLAT701_ALERT_1_A Bond Calc 6.1668(6), Rep 4.1539(5), Dev.. 3354.83 Sigma
I2 -Au1 1.555 2.000 ........ # 20 Check
PLAT971_ALERT_2_A Check Calcd Resid. Dens. 0.71A From I2 3.80 eA-3
PLAT973_ALERT_2_A Check Calcd Positive Resid. Density on Au2 3.08 eA-3
PLAT973_ALERT_2_A Check Calcd Positive Resid. Density on Au1 2.26 eA-3
Alert level B
PLAT972_ALERT_2_B Check Calcd Resid. Dens. 0.50A From I1 -2.75 eA-3
PLAT972_ALERT_2_B Check Calcd Resid. Dens. 0.48A From I1 -2.56 eA-3
Alert level C
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.01067 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 ..I1 . 3.28 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 ..I2 . 3.22 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A ..I1 . 3.28 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A ..I1 . 3.16 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B ..I2 . 3.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C ..I1 . 3.29 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3' ..I2 . 3.08 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4'2 ..I2 . 3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7'1 ..I2 . 3.19 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note
C14 H22 Au Br2 I2 N4
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 1.75A From C3' 2.43 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 0.63A From Au1 2.43 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 0.64A From Br2 2.21 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 0.82A From I2 2.18 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 0.56A From Au1 1.78 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 0.38A From Br2 1.74 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens. 1.58A From I1 1.56 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens. 0.44A From I1 -2.50 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 12.46 Why ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Au1 --I1 . 12.0 s.u.
PLAT434_ALERT_2_G Short Inter HL..HL Contact I1 ..I2 3.51 Ang.
-x,-y,-z = 2_555 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact I2 ..Br1 3.43 Ang.
x,y,z = 1_555 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact I2 ..Br2 3.56 Ang.
x,y,z = 1_555 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 10 Note
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.15 Ratio
PLAT774_ALERT_1_G Check X-Y Bond in CIF: I2 --Au1 .. 4.15 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note
4 ALERT level A = Most likely a serious problem - resolve or explain
2 ALERT level B = A potentially serious problem, consider carefully
21 ALERT level C = Check. Ensure it is not caused by an omission or oversight
10 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
20 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
12 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: Siemens XP (Siemens, 1994); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015).
Bis(4-bromo-1,3-diethylimidazol-2-ylidene)gold(I) iodide (3)
top
Crystal data top
[Au(C7H11BrN2)2]I | Z = 2 |
Mr = 730.04 | F(000) = 672 |
Triclinic, P1 | Dx = 2.396 Mg m−3 |
a = 8.4676 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.8248 (3) Å | Cell parameters from 47541 reflections |
c = 14.0119 (5) Å | θ = 2.7–36.4° |
α = 76.374 (3)° | µ = 12.74 mm−1 |
β = 85.320 (2)° | T = 100 K |
γ = 85.251 (2)° | Block, colourless |
V = 1011.99 (6) Å3 | 0.09 × 0.06 × 0.05 mm |
Data collection top
XtaLAB Synergy, HyPix diffractometer | 9374 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 8185 reflections with I > 2σ(I) |
Detector resolution: 10.0000 pixels mm-1 | Rint = 0.043 |
ω scans | θmax = 36.7°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −14→14 |
Tmin = 0.751, Tmax = 1.000 | k = −14→14 |
84327 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0219P)2 + 1.6441P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
9374 reflections | Δρmax = 1.53 e Å−3 |
203 parameters | Δρmin = −2.02 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.46224 (2) | 0.71713 (2) | 0.23616 (2) | 0.01505 (2) | |
I1 | 0.25568 (2) | −0.12579 (2) | 0.72649 (2) | 0.01947 (3) | |
Br1 | 0.90742 (3) | 0.85910 (3) | −0.11585 (2) | 0.01837 (4) | |
Br2 | 0.22321 (3) | 0.27369 (3) | 0.58678 (2) | 0.02294 (5) | |
N1 | 0.7026 (2) | 0.8013 (2) | 0.06168 (14) | 0.0144 (3) | |
N2 | 0.4687 (2) | 0.7981 (2) | 0.01341 (14) | 0.0151 (3) | |
N3 | 0.3414 (2) | 0.4840 (2) | 0.41402 (14) | 0.0158 (3) | |
N4 | 0.3267 (2) | 0.7110 (2) | 0.44721 (14) | 0.0168 (3) | |
C1 | 0.5490 (3) | 0.7807 (3) | 0.09487 (17) | 0.0152 (4) | |
C2 | 0.7156 (3) | 0.8303 (3) | −0.03991 (16) | 0.0150 (4) | |
C3 | 0.5681 (3) | 0.8289 (3) | −0.07101 (17) | 0.0159 (4) | |
H3 | 0.539432 | 0.845625 | −0.137005 | 0.019* | |
C4 | 0.8329 (3) | 0.7876 (3) | 0.12682 (17) | 0.0190 (4) | |
H4A | 0.796328 | 0.835665 | 0.182530 | 0.023* | |
H4B | 0.922392 | 0.845773 | 0.090037 | 0.023* | |
C5 | 0.8904 (3) | 0.6186 (3) | 0.1667 (2) | 0.0268 (5) | |
H5A | 0.802277 | 0.560658 | 0.203377 | 0.040* | |
H5B | 0.975985 | 0.614518 | 0.210455 | 0.040* | |
H5C | 0.930249 | 0.571616 | 0.111832 | 0.040* | |
C6 | 0.3003 (3) | 0.7693 (3) | 0.01381 (19) | 0.0190 (4) | |
H6A | 0.251033 | 0.845711 | −0.041004 | 0.023* | |
H6B | 0.244648 | 0.783981 | 0.076250 | 0.023* | |
C7 | 0.2815 (3) | 0.6044 (3) | 0.0029 (2) | 0.0253 (5) | |
H7A | 0.335813 | 0.590123 | −0.059152 | 0.038* | |
H7B | 0.168425 | 0.588003 | 0.002906 | 0.038* | |
H7C | 0.328132 | 0.528699 | 0.057982 | 0.038* | |
C8 | 0.3723 (3) | 0.6350 (3) | 0.37528 (17) | 0.0164 (4) | |
C9 | 0.2739 (3) | 0.4672 (3) | 0.50878 (17) | 0.0175 (4) | |
C10 | 0.2644 (3) | 0.6105 (3) | 0.53014 (17) | 0.0190 (4) | |
H10 | 0.223233 | 0.636119 | 0.589902 | 0.023* | |
C11 | 0.3707 (3) | 0.3610 (3) | 0.35936 (19) | 0.0208 (4) | |
H11A | 0.380137 | 0.258081 | 0.406376 | 0.025* | |
H11B | 0.472452 | 0.376079 | 0.319289 | 0.025* | |
C12 | 0.2385 (4) | 0.3624 (3) | 0.2928 (2) | 0.0292 (6) | |
H12A | 0.137555 | 0.348228 | 0.332223 | 0.044* | |
H12B | 0.260413 | 0.277190 | 0.258600 | 0.044* | |
H12C | 0.231993 | 0.462511 | 0.244325 | 0.044* | |
C13 | 0.3265 (3) | 0.8808 (3) | 0.43601 (19) | 0.0204 (4) | |
H13A | 0.407523 | 0.923764 | 0.383801 | 0.024* | |
H13B | 0.354381 | 0.903198 | 0.498325 | 0.024* | |
C14 | 0.1657 (4) | 0.9582 (3) | 0.4096 (3) | 0.0367 (7) | |
H14A | 0.140898 | 0.940989 | 0.346040 | 0.055* | |
H14B | 0.166327 | 1.070607 | 0.405280 | 0.055* | |
H14C | 0.085156 | 0.913349 | 0.460390 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.01531 (4) | 0.01589 (4) | 0.01371 (4) | −0.00177 (3) | 0.00196 (3) | −0.00363 (3) |
I1 | 0.02119 (7) | 0.02104 (7) | 0.01555 (6) | 0.00120 (5) | 0.00096 (5) | −0.00454 (5) |
Br1 | 0.01523 (10) | 0.02506 (11) | 0.01603 (9) | −0.00645 (8) | 0.00254 (7) | −0.00658 (8) |
Br2 | 0.03080 (13) | 0.02037 (11) | 0.01701 (10) | −0.00987 (9) | −0.00213 (9) | −0.00004 (8) |
N1 | 0.0136 (8) | 0.0164 (8) | 0.0137 (8) | −0.0021 (6) | 0.0003 (6) | −0.0045 (6) |
N2 | 0.0129 (8) | 0.0163 (8) | 0.0155 (8) | −0.0007 (6) | 0.0000 (6) | −0.0031 (7) |
N3 | 0.0170 (8) | 0.0159 (8) | 0.0149 (8) | −0.0017 (7) | −0.0007 (6) | −0.0040 (7) |
N4 | 0.0204 (9) | 0.0153 (8) | 0.0148 (8) | −0.0032 (7) | −0.0003 (7) | −0.0035 (7) |
C1 | 0.0139 (9) | 0.0155 (9) | 0.0165 (9) | −0.0023 (7) | 0.0017 (7) | −0.0046 (7) |
C2 | 0.0152 (9) | 0.0172 (9) | 0.0128 (8) | −0.0035 (7) | 0.0011 (7) | −0.0038 (7) |
C3 | 0.0149 (9) | 0.0178 (10) | 0.0153 (9) | −0.0021 (7) | 0.0001 (7) | −0.0045 (8) |
C4 | 0.0176 (10) | 0.0256 (11) | 0.0157 (9) | −0.0056 (8) | −0.0020 (8) | −0.0070 (8) |
C5 | 0.0241 (12) | 0.0309 (14) | 0.0253 (12) | 0.0050 (10) | −0.0074 (10) | −0.0065 (10) |
C6 | 0.0119 (9) | 0.0231 (11) | 0.0217 (10) | −0.0001 (8) | −0.0017 (8) | −0.0049 (9) |
C7 | 0.0201 (11) | 0.0243 (12) | 0.0330 (13) | −0.0066 (9) | −0.0003 (10) | −0.0081 (10) |
C8 | 0.0153 (9) | 0.0167 (9) | 0.0169 (9) | −0.0016 (7) | −0.0004 (7) | −0.0036 (8) |
C9 | 0.0211 (10) | 0.0171 (10) | 0.0136 (9) | −0.0045 (8) | −0.0012 (8) | −0.0011 (8) |
C10 | 0.0218 (11) | 0.0199 (10) | 0.0151 (9) | −0.0047 (8) | 0.0014 (8) | −0.0037 (8) |
C11 | 0.0251 (12) | 0.0174 (10) | 0.0212 (11) | −0.0008 (9) | −0.0005 (9) | −0.0075 (9) |
C12 | 0.0391 (16) | 0.0252 (13) | 0.0264 (13) | −0.0052 (11) | −0.0088 (11) | −0.0085 (10) |
C13 | 0.0271 (12) | 0.0143 (10) | 0.0200 (10) | −0.0054 (8) | 0.0024 (9) | −0.0042 (8) |
C14 | 0.0328 (16) | 0.0179 (12) | 0.056 (2) | 0.0019 (11) | −0.0004 (14) | −0.0034 (13) |
Geometric parameters (Å, º) top
Au1—C1 | 2.020 (2) | C13—C14 | 1.506 (4) |
Au1—C8 | 2.022 (2) | C3—H3 | 0.9500 |
I1—Br1i | 3.5294 (3) | C4—H4A | 0.9900 |
I1—Br2 | 3.6072 (3) | C4—H4B | 0.9900 |
Au1—Br2ii | 3.8033 (3) | C5—H5A | 0.9800 |
Br1—C2 | 1.869 (2) | C5—H5B | 0.9800 |
Br2—C9 | 1.861 (2) | C5—H5C | 0.9800 |
N1—C1 | 1.357 (3) | C6—H6A | 0.9900 |
N1—C2 | 1.382 (3) | C6—H6B | 0.9900 |
N1—C4 | 1.468 (3) | C7—H7A | 0.9800 |
N2—C1 | 1.348 (3) | C7—H7B | 0.9800 |
N2—C3 | 1.381 (3) | C7—H7C | 0.9800 |
N2—C6 | 1.468 (3) | C10—H10 | 0.9500 |
N3—C8 | 1.354 (3) | C11—H11A | 0.9900 |
N3—C9 | 1.382 (3) | C11—H11B | 0.9900 |
N3—C11 | 1.464 (3) | C12—H12A | 0.9800 |
N4—C8 | 1.351 (3) | C12—H12B | 0.9800 |
N4—C10 | 1.381 (3) | C12—H12C | 0.9800 |
N4—C13 | 1.469 (3) | C13—H13A | 0.9900 |
C2—C3 | 1.357 (3) | C13—H13B | 0.9900 |
C4—C5 | 1.518 (4) | C14—H14A | 0.9800 |
C6—C7 | 1.521 (4) | C14—H14B | 0.9800 |
C9—C10 | 1.361 (3) | C14—H14C | 0.9800 |
C11—C12 | 1.512 (4) | | |
| | | |
C1—Au1—C8 | 174.97 (9) | C4—C5—H5A | 109.5 |
Br1i—I1—Br2 | 101.436 (8) | C4—C5—H5B | 109.5 |
C2—Br1—I1iii | 172.43 (7) | H5A—C5—H5B | 109.5 |
C9—Br2—I1 | 162.21 (8) | C4—C5—H5C | 109.5 |
C1—N1—C2 | 109.82 (19) | H5A—C5—H5C | 109.5 |
C1—N1—C4 | 123.48 (19) | H5B—C5—H5C | 109.5 |
C2—N1—C4 | 126.65 (19) | N2—C6—H6A | 109.5 |
C1—N2—C3 | 111.61 (19) | C7—C6—H6A | 109.5 |
C1—N2—C6 | 124.54 (19) | N2—C6—H6B | 109.5 |
C3—N2—C6 | 123.46 (19) | C7—C6—H6B | 109.5 |
C8—N3—C9 | 110.15 (19) | H6A—C6—H6B | 108.1 |
C8—N3—C11 | 123.4 (2) | C6—C7—H7A | 109.5 |
C9—N3—C11 | 126.4 (2) | C6—C7—H7B | 109.5 |
C8—N4—C10 | 111.1 (2) | H7A—C7—H7B | 109.5 |
C8—N4—C13 | 124.9 (2) | C6—C7—H7C | 109.5 |
C10—N4—C13 | 123.7 (2) | H7A—C7—H7C | 109.5 |
N2—C1—N1 | 105.25 (19) | H7B—C7—H7C | 109.5 |
N2—C1—Au1 | 127.11 (16) | C9—C10—H10 | 127.0 |
N1—C1—Au1 | 127.41 (17) | N4—C10—H10 | 127.0 |
C3—C2—N1 | 107.77 (19) | N3—C11—H11A | 109.3 |
C3—C2—Br1 | 128.16 (17) | C12—C11—H11A | 109.3 |
N1—C2—Br1 | 124.05 (17) | N3—C11—H11B | 109.3 |
C2—C3—N2 | 105.6 (2) | C12—C11—H11B | 109.3 |
N1—C4—C5 | 112.1 (2) | H11A—C11—H11B | 108.0 |
N2—C6—C7 | 110.9 (2) | C11—C12—H12A | 109.5 |
N4—C8—N3 | 105.41 (19) | C11—C12—H12B | 109.5 |
N4—C8—Au1 | 130.27 (17) | H12A—C12—H12B | 109.5 |
N3—C8—Au1 | 124.30 (17) | C11—C12—H12C | 109.5 |
C10—C9—N3 | 107.3 (2) | H12A—C12—H12C | 109.5 |
C10—C9—Br2 | 130.48 (18) | H12B—C12—H12C | 109.5 |
N3—C9—Br2 | 122.09 (17) | N4—C13—H13A | 109.5 |
C9—C10—N4 | 106.0 (2) | C14—C13—H13A | 109.5 |
N3—C11—C12 | 111.5 (2) | N4—C13—H13B | 109.5 |
N4—C13—C14 | 110.6 (2) | C14—C13—H13B | 109.5 |
C2—C3—H3 | 127.2 | H13A—C13—H13B | 108.1 |
N2—C3—H3 | 127.2 | C13—C14—H14A | 109.5 |
N1—C4—H4A | 109.2 | C13—C14—H14B | 109.5 |
C5—C4—H4A | 109.2 | H14A—C14—H14B | 109.5 |
N1—C4—H4B | 109.2 | C13—C14—H14C | 109.5 |
C5—C4—H4B | 109.2 | H14A—C14—H14C | 109.5 |
H4A—C4—H4B | 107.9 | H14B—C14—H14C | 109.5 |
| | | |
C3—N2—C1—N1 | 0.2 (3) | C13—N4—C8—N3 | −175.0 (2) |
C6—N2—C1—N1 | 173.2 (2) | C10—N4—C8—Au1 | 177.04 (18) |
C3—N2—C1—Au1 | −174.55 (17) | C13—N4—C8—Au1 | 3.3 (4) |
C6—N2—C1—Au1 | −1.5 (3) | C9—N3—C8—N4 | 1.3 (3) |
C2—N1—C1—N2 | −0.3 (2) | C11—N3—C8—N4 | 178.8 (2) |
C4—N1—C1—N2 | −178.1 (2) | C9—N3—C8—Au1 | −177.17 (17) |
C2—N1—C1—Au1 | 174.36 (16) | C11—N3—C8—Au1 | 0.4 (3) |
C4—N1—C1—Au1 | −3.4 (3) | C8—N3—C9—C10 | −0.8 (3) |
C1—N1—C2—C3 | 0.4 (3) | C11—N3—C9—C10 | −178.3 (2) |
C4—N1—C2—C3 | 178.1 (2) | C8—N3—C9—Br2 | −177.42 (17) |
C1—N1—C2—Br1 | −177.92 (17) | C11—N3—C9—Br2 | 5.1 (3) |
C4—N1—C2—Br1 | −0.2 (3) | I1—Br2—C9—C10 | −114.8 (3) |
N1—C2—C3—N2 | −0.3 (3) | I1—Br2—C9—N3 | 61.0 (4) |
Br1—C2—C3—N2 | 177.95 (17) | N3—C9—C10—N4 | 0.0 (3) |
C1—N2—C3—C2 | 0.1 (3) | Br2—C9—C10—N4 | 176.24 (19) |
C6—N2—C3—C2 | −173.1 (2) | C8—N4—C10—C9 | 0.8 (3) |
C1—N1—C4—C5 | 81.0 (3) | C13—N4—C10—C9 | 174.6 (2) |
C2—N1—C4—C5 | −96.4 (3) | C8—N3—C11—C12 | −80.8 (3) |
C1—N2—C6—C7 | −94.9 (3) | C9—N3—C11—C12 | 96.4 (3) |
C3—N2—C6—C7 | 77.4 (3) | C8—N4—C13—C14 | 94.0 (3) |
C10—N4—C8—N3 | −1.3 (3) | C10—N4—C13—C14 | −79.0 (3) |
Symmetry codes: (i) x−1, y−1, z+1; (ii) −x+1, −y+1, −z+1; (iii) x+1, y+1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···I1iv | 0.95 | 3.15 | 3.966 (2) | 145 |
C4—H4A···I1ii | 0.99 | 3.10 | 3.995 (3) | 151 |
C6—H6A···I1iv | 0.99 | 3.21 | 3.955 (3) | 134 |
C10—H10···I1v | 0.95 | 3.20 | 3.993 (2) | 142 |
C11—H11A···Br2 | 0.99 | 2.79 | 3.265 (3) | 110 |
C11—H11B···I1vi | 0.99 | 3.19 | 3.903 (3) | 130 |
C12—H12B···Br1vii | 0.98 | 3.06 | 3.831 (3) | 137 |
C13—H13B···I1v | 0.99 | 3.19 | 4.053 (3) | 146 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iv) x, y+1, z−1; (v) x, y+1, z; (vi) −x+1, −y, −z+1; (vii) −x+1, −y+1, −z. |
Bis(4-bromo-1,3-diethylimidazol-2-ylidene)gold(I)
trans-bis(4-bromo-1,3-diethyl-imidazol-2-ylidene)diiodidogold(III)
diiodide (4)
top
Crystal data top
[Au(C7H11BrN2)2][AuI2(C7H11BrN2)2]I2 | Z = 1 |
Mr = 1713.88 | F(000) = 778 |
Triclinic, P1 | Dx = 2.607 Mg m−3 |
a = 8.0245 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5782 (3) Å | Cell parameters from 24546 reflections |
c = 15.9814 (6) Å | θ = 2.6–34.1° |
α = 91.228 (3)° | µ = 13.23 mm−1 |
β = 96.517 (4)° | T = 100 K |
γ = 92.255 (4)° | Plate, brown |
V = 1091.77 (8) Å3 | 0.08 × 0.03 × 0.01 mm |
Data collection top
XtaLAB Synergy, HyPix diffractometer | 6378 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 5409 reflections with I > 2σ(I) |
Detector resolution: 10.0000 pixels mm-1 | Rint = 0.048 |
ω scans | θmax = 30.0°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −11→11 |
Tmin = 0.703, Tmax = 1.000 | k = −12→12 |
61886 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0494P)2 + 12.4607P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6378 reflections | Δρmax = 3.97 e Å−3 |
215 parameters | Δρmin = −2.66 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | −0.500000 | −0.500000 | 0.000000 | 0.01890 (8) | |
I1 | −0.36292 (6) | −0.37952 (6) | −0.12916 (3) | 0.02666 (11) | |
Br1 | −0.00401 (10) | −0.09434 (9) | 0.21316 (5) | 0.02965 (16) | |
N1 | −0.2548 (7) | −0.2807 (7) | 0.1082 (4) | 0.0227 (11) | |
N2 | −0.1732 (7) | −0.5172 (7) | 0.1164 (4) | 0.0218 (11) | |
C1 | −0.2957 (9) | −0.4283 (8) | 0.0806 (4) | 0.0199 (12) | |
C2 | −0.1053 (9) | −0.2781 (8) | 0.1624 (4) | 0.0236 (13) | |
C3 | −0.0556 (9) | −0.4261 (8) | 0.1680 (4) | 0.0242 (13) | |
H3 | 0.041194 | −0.461233 | 0.200890 | 0.029* | |
C4 | −0.3602 (10) | −0.1472 (8) | 0.0908 (5) | 0.0282 (15) | |
H4A | −0.426098 | −0.163377 | 0.034872 | 0.034* | |
H4B | −0.287389 | −0.051785 | 0.088776 | 0.034* | |
C5 | −0.4806 (13) | −0.1229 (11) | 0.1572 (6) | 0.042 (2) | |
H5A | −0.548069 | −0.219305 | 0.162128 | 0.064* | |
H5B | −0.554816 | −0.038287 | 0.140329 | 0.064* | |
H5C | −0.415991 | −0.095597 | 0.211660 | 0.064* | |
C6 | −0.1643 (9) | −0.6878 (8) | 0.1038 (4) | 0.0243 (13) | |
H6A | −0.276204 | −0.738050 | 0.107783 | 0.029* | |
H6B | −0.084560 | −0.728786 | 0.149017 | 0.029* | |
C7 | −0.1087 (11) | −0.7291 (10) | 0.0196 (5) | 0.0343 (17) | |
H7A | −0.194248 | −0.699822 | −0.025403 | 0.051* | |
H7B | −0.093445 | −0.841752 | 0.015793 | 0.051* | |
H7C | −0.002321 | −0.672810 | 0.013535 | 0.051* | |
Au2 | 1.000000 | 1.000000 | 0.500000 | 0.02101 (9) | |
I2 | 0.18002 (6) | 0.24488 (5) | 0.30519 (3) | 0.02377 (10) | |
Br2 | 0.40896 (9) | 0.59948 (8) | 0.36840 (4) | 0.02459 (14) | |
N1' | 0.7026 (7) | 0.7839 (6) | 0.4369 (3) | 0.0198 (11) | |
N2' | 0.6387 (8) | 1.0226 (6) | 0.4186 (4) | 0.0219 (11) | |
C1' | 0.7658 (9) | 0.9331 (7) | 0.4491 (4) | 0.0203 (12) | |
C2' | 0.5388 (9) | 0.7821 (8) | 0.3989 (4) | 0.0216 (12) | |
C3' | 0.4977 (9) | 0.9322 (8) | 0.3871 (4) | 0.0215 (12) | |
H3' | 0.393497 | 0.968182 | 0.362203 | 0.026* | |
C4' | 0.8021 (9) | 0.6466 (8) | 0.4567 (4) | 0.0224 (13) | |
H4'1 | 0.725634 | 0.555349 | 0.463211 | 0.027* | |
H4'2 | 0.873672 | 0.665833 | 0.510905 | 0.027* | |
C5' | 0.9122 (10) | 0.6105 (8) | 0.3881 (5) | 0.0290 (15) | |
H5'1 | 0.841801 | 0.593654 | 0.334152 | 0.044* | |
H5'2 | 0.973515 | 0.516180 | 0.402016 | 0.044* | |
H5'3 | 0.992338 | 0.698354 | 0.383758 | 0.044* | |
C6' | 0.6523 (10) | 1.1916 (8) | 0.4105 (5) | 0.0259 (14) | |
H6'1 | 0.746773 | 1.235149 | 0.450502 | 0.031* | |
H6'2 | 0.547969 | 1.238037 | 0.425063 | 0.031* | |
C7' | 0.6810 (9) | 1.2344 (8) | 0.3214 (5) | 0.0281 (15) | |
H7'1 | 0.785274 | 1.189945 | 0.307254 | 0.042* | |
H7'2 | 0.689663 | 1.348279 | 0.317476 | 0.042* | |
H7'3 | 0.586704 | 1.192742 | 0.281833 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.02247 (17) | 0.01893 (16) | 0.01489 (15) | −0.00122 (12) | 0.00110 (12) | 0.00024 (12) |
I1 | 0.0288 (2) | 0.0301 (2) | 0.0214 (2) | −0.00043 (18) | 0.00418 (16) | 0.00327 (17) |
Br1 | 0.0348 (4) | 0.0248 (3) | 0.0272 (3) | −0.0053 (3) | −0.0026 (3) | −0.0047 (3) |
N1 | 0.025 (3) | 0.023 (3) | 0.020 (3) | 0.000 (2) | 0.004 (2) | −0.002 (2) |
N2 | 0.022 (3) | 0.021 (3) | 0.021 (3) | −0.002 (2) | −0.001 (2) | −0.003 (2) |
C1 | 0.028 (3) | 0.018 (3) | 0.013 (3) | −0.002 (2) | 0.002 (2) | −0.001 (2) |
C2 | 0.028 (3) | 0.024 (3) | 0.018 (3) | −0.004 (3) | 0.001 (2) | −0.003 (2) |
C3 | 0.028 (3) | 0.027 (3) | 0.017 (3) | 0.000 (3) | 0.000 (2) | −0.004 (2) |
C4 | 0.039 (4) | 0.019 (3) | 0.025 (3) | −0.001 (3) | 0.000 (3) | −0.002 (3) |
C5 | 0.051 (5) | 0.035 (4) | 0.042 (5) | 0.004 (4) | 0.014 (4) | −0.008 (4) |
C6 | 0.028 (3) | 0.021 (3) | 0.024 (3) | 0.001 (3) | 0.002 (3) | 0.000 (3) |
C7 | 0.042 (5) | 0.031 (4) | 0.031 (4) | 0.005 (3) | 0.005 (3) | −0.007 (3) |
Au2 | 0.02690 (18) | 0.01581 (16) | 0.01892 (16) | 0.00103 (12) | −0.00311 (13) | −0.00180 (12) |
I2 | 0.0231 (2) | 0.0219 (2) | 0.0252 (2) | −0.00092 (15) | −0.00093 (16) | −0.00113 (16) |
Br2 | 0.0266 (3) | 0.0199 (3) | 0.0267 (3) | −0.0050 (2) | 0.0032 (3) | −0.0015 (2) |
N1' | 0.028 (3) | 0.014 (2) | 0.017 (2) | −0.001 (2) | 0.001 (2) | 0.0007 (19) |
N2' | 0.028 (3) | 0.015 (2) | 0.022 (3) | 0.001 (2) | −0.001 (2) | −0.002 (2) |
C1' | 0.031 (3) | 0.014 (3) | 0.015 (3) | 0.004 (2) | 0.000 (2) | 0.000 (2) |
C2' | 0.024 (3) | 0.020 (3) | 0.022 (3) | 0.000 (2) | 0.005 (2) | 0.000 (2) |
C3' | 0.025 (3) | 0.017 (3) | 0.021 (3) | 0.000 (2) | −0.002 (2) | −0.002 (2) |
C4' | 0.026 (3) | 0.016 (3) | 0.026 (3) | 0.007 (2) | 0.008 (3) | 0.002 (2) |
C5' | 0.031 (4) | 0.019 (3) | 0.039 (4) | 0.008 (3) | 0.010 (3) | 0.001 (3) |
C6' | 0.031 (4) | 0.015 (3) | 0.029 (3) | 0.002 (3) | −0.005 (3) | −0.001 (3) |
C7' | 0.025 (3) | 0.022 (3) | 0.038 (4) | 0.000 (3) | 0.008 (3) | 0.008 (3) |
Geometric parameters (Å, º) top
Au1—C1i | 2.033 (7) | N2'—C6' | 1.459 (9) |
Au1—C1 | 2.033 (7) | C2'—C3' | 1.353 (9) |
Au1—I1i | 2.6564 (5) | C4'—C5' | 1.519 (10) |
Au1—I1 | 2.6564 (5) | C6'—C7' | 1.519 (11) |
I1—I2ii | 3.5136 (7) | C3—H3 | 0.9500 |
Br1—C2 | 1.870 (7) | C4—H4A | 0.9900 |
Br1—I2 | 3.4347 (8) | C4—H4B | 0.9900 |
N1—C1 | 1.347 (8) | C5—H5A | 0.9800 |
N1—C2 | 1.397 (9) | C5—H5B | 0.9800 |
N1—C4 | 1.464 (10) | C5—H5C | 0.9800 |
N2—C1 | 1.351 (9) | C6—H6A | 0.9900 |
N2—C3 | 1.385 (8) | C6—H6B | 0.9900 |
N2—C6 | 1.479 (9) | C7—H7A | 0.9800 |
C2—C3 | 1.348 (10) | C7—H7B | 0.9800 |
C4—C5 | 1.530 (12) | C7—H7C | 0.9800 |
C6—C7 | 1.504 (11) | C3'—H3' | 0.9500 |
Au2—C1' | 2.018 (7) | C4'—H4'1 | 0.9900 |
Au2—C1'iii | 2.018 (7) | C4'—H4'2 | 0.9900 |
I2—Br2 | 3.5575 (8) | C5'—H5'1 | 0.9800 |
I2—Au1ii | 4.1539 (5) | C5'—H5'2 | 0.9800 |
Br2—C2' | 1.871 (7) | C5'—H5'3 | 0.9800 |
N1'—C1' | 1.360 (8) | C6'—H6'1 | 0.9900 |
N1'—C2' | 1.383 (9) | C6'—H6'2 | 0.9900 |
N1'—C4' | 1.469 (8) | C7'—H7'1 | 0.9800 |
N2'—C1' | 1.354 (9) | C7'—H7'2 | 0.9800 |
N2'—C3' | 1.386 (9) | C7'—H7'3 | 0.9800 |
| | | |
C1i—Au1—C1 | 180.0 | N2—C3—H3 | 126.7 |
C1i—Au1—I1i | 90.95 (18) | N1—C4—H4A | 109.1 |
C1—Au1—I1i | 89.05 (18) | C5—C4—H4A | 109.1 |
C1i—Au1—I1 | 89.05 (18) | N1—C4—H4B | 109.1 |
C1—Au1—I1 | 90.95 (18) | C5—C4—H4B | 109.1 |
I1i—Au1—I1 | 180.0 | H4A—C4—H4B | 107.8 |
Au1—I1—I2ii | 176.29 (2) | C4—C5—H5A | 109.5 |
C2—Br1—I2 | 179.5 (2) | C4—C5—H5B | 109.5 |
C1—N1—C2 | 109.5 (6) | H5A—C5—H5B | 109.5 |
C1—N1—C4 | 124.8 (6) | C4—C5—H5C | 109.5 |
C2—N1—C4 | 125.3 (6) | H5A—C5—H5C | 109.5 |
C1—N2—C3 | 110.4 (6) | H5B—C5—H5C | 109.5 |
C1—N2—C6 | 125.6 (6) | N2—C6—H6A | 109.3 |
C3—N2—C6 | 124.0 (6) | C7—C6—H6A | 109.3 |
N1—C1—N2 | 106.2 (6) | N2—C6—H6B | 109.3 |
N1—C1—Au1 | 126.4 (5) | C7—C6—H6B | 109.3 |
N2—C1—Au1 | 127.4 (5) | H6A—C6—H6B | 107.9 |
C3—C2—N1 | 107.2 (6) | C6—C7—H7A | 109.5 |
C3—C2—Br1 | 129.9 (6) | C6—C7—H7B | 109.5 |
N1—C2—Br1 | 122.9 (5) | H7A—C7—H7B | 109.5 |
C2—C3—N2 | 106.6 (6) | C6—C7—H7C | 109.5 |
N1—C4—C5 | 112.6 (7) | H7A—C7—H7C | 109.5 |
N2—C6—C7 | 111.8 (6) | H7B—C7—H7C | 109.5 |
C1'—Au2—C1'iii | 180.0 | C2'—C3'—H3' | 127.0 |
Br1—I2—I1ii | 97.240 (19) | N2'—C3'—H3' | 127.0 |
Br1—I2—Br2 | 169.87 (2) | N1'—C4'—H4'1 | 109.3 |
I1ii—I2—Br2 | 72.852 (17) | C5'—C4'—H4'1 | 109.3 |
Br1—I2—Au2iv | 74.604 (16) | N1'—C4'—H4'2 | 109.3 |
I1ii—I2—Au2iv | 168.488 (16) | C5'—C4'—H4'2 | 109.3 |
Br2—I2—Au2iv | 114.871 (16) | H4'1—C4'—H4'2 | 108.0 |
C2'—Br2—I2 | 177.0 (2) | C4'—C5'—H5'1 | 109.5 |
C1'—N1'—C2' | 110.4 (6) | C4'—C5'—H5'2 | 109.5 |
C1'—N1'—C4' | 123.3 (6) | H5'1—C5'—H5'2 | 109.5 |
C2'—N1'—C4' | 126.1 (6) | C4'—C5'—H5'3 | 109.5 |
C1'—N2'—C3' | 111.4 (6) | H5'1—C5'—H5'3 | 109.5 |
C1'—N2'—C6' | 124.9 (6) | H5'2—C5'—H5'3 | 109.5 |
C3'—N2'—C6' | 123.3 (6) | N2'—C6'—H6'1 | 109.4 |
N2'—C1'—N1' | 104.7 (6) | C7'—C6'—H6'1 | 109.4 |
N2'—C1'—Au2 | 128.9 (5) | N2'—C6'—H6'2 | 109.4 |
N1'—C1'—Au2 | 126.4 (5) | C7'—C6'—H6'2 | 109.4 |
C3'—C2'—N1' | 107.4 (6) | H6'1—C6'—H6'2 | 108.0 |
C3'—C2'—Br2 | 128.7 (5) | C6'—C7'—H7'1 | 109.5 |
N1'—C2'—Br2 | 123.9 (5) | C6'—C7'—H7'2 | 109.5 |
C2'—C3'—N2' | 105.9 (6) | H7'1—C7'—H7'2 | 109.5 |
N1'—C4'—C5' | 111.4 (6) | C6'—C7'—H7'3 | 109.5 |
N2'—C6'—C7' | 111.0 (6) | H7'1—C7'—H7'3 | 109.5 |
C2—C3—H3 | 126.7 | H7'2—C7'—H7'3 | 109.5 |
| | | |
C2—N1—C1—N2 | −0.4 (7) | C3'—N2'—C1'—N1' | −0.4 (8) |
C4—N1—C1—N2 | −174.5 (6) | C6'—N2'—C1'—N1' | −173.8 (6) |
C2—N1—C1—Au1 | −179.8 (5) | C3'—N2'—C1'—Au2 | 178.6 (5) |
C4—N1—C1—Au1 | 6.2 (10) | C6'—N2'—C1'—Au2 | 5.3 (10) |
C3—N2—C1—N1 | 1.0 (8) | C2'—N1'—C1'—N2' | 0.4 (7) |
C6—N2—C1—N1 | −179.5 (6) | C4'—N1'—C1'—N2' | 176.4 (6) |
C3—N2—C1—Au1 | −179.7 (5) | C2'—N1'—C1'—Au2 | −178.8 (5) |
C6—N2—C1—Au1 | −0.2 (10) | C4'—N1'—C1'—Au2 | −2.7 (9) |
C1—N1—C2—C3 | −0.3 (8) | C1'—N1'—C2'—C3' | −0.1 (8) |
C4—N1—C2—C3 | 173.8 (7) | C4'—N1'—C2'—C3' | −176.1 (6) |
C1—N1—C2—Br1 | 179.1 (5) | C1'—N1'—C2'—Br2 | 178.1 (5) |
C4—N1—C2—Br1 | −6.8 (10) | C4'—N1'—C2'—Br2 | 2.2 (9) |
N1—C2—C3—N2 | 0.9 (8) | N1'—C2'—C3'—N2' | −0.1 (8) |
Br1—C2—C3—N2 | −178.5 (5) | Br2—C2'—C3'—N2' | −178.3 (5) |
C1—N2—C3—C2 | −1.2 (8) | C1'—N2'—C3'—C2' | 0.4 (8) |
C6—N2—C3—C2 | 179.3 (6) | C6'—N2'—C3'—C2' | 173.8 (6) |
C1—N1—C4—C5 | 89.5 (8) | C1'—N1'—C4'—C5' | −79.6 (8) |
C2—N1—C4—C5 | −83.7 (9) | C2'—N1'—C4'—C5' | 95.8 (8) |
C1—N2—C6—C7 | 76.1 (9) | C1'—N2'—C6'—C7' | 97.4 (8) |
C3—N2—C6—C7 | −104.5 (8) | C3'—N2'—C6'—C7' | −75.2 (9) |
Symmetry codes: (i) −x−1, −y−1, −z; (ii) −x, −y, −z; (iii) −x+2, −y+2, −z+1; (iv) x−1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···I1v | 0.95 | 3.28 | 3.913 (7) | 126 |
C3—H3···I2vi | 0.95 | 3.22 | 4.011 (7) | 142 |
C4—H4A···I1 | 0.99 | 3.28 | 4.002 (7) | 132 |
C6—H6A···I1i | 0.99 | 3.16 | 3.925 (7) | 136 |
C6—H6B···I2vi | 0.99 | 3.11 | 4.064 (7) | 163 |
C7—H7C···I1v | 0.98 | 3.29 | 4.051 (9) | 136 |
C3′—H3′···I2vii | 0.95 | 3.08 | 3.916 (7) | 148 |
C4′—H4′2···I2viii | 0.99 | 3.10 | 3.883 (7) | 137 |
C7′—H7′1···I2ix | 0.98 | 3.19 | 4.039 (7) | 146 |
Symmetry codes: (i) −x−1, −y−1, −z; (v) −x, −y−1, −z; (vi) x, y−1, z; (vii) x, y+1, z; (viii) −x+1, −y+1, −z+1; (ix) x+1, y+1, z. |