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In the first title compound, [Au(C7H11BrN2)2]I, the cations and anions form chains via halogen bond linkages Br...I...Br. The second title compound, [Au(C7H11BrN2)2][AuI2(C7H11BrN2)2]I2, forms a layer structure involving Br...I...Br and I...I...Au linkages.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021011488/yz2012sup1.cif
Contains datablocks 3, 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021011488/yz20123sup2.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021011488/yz20124sup3.hkl
Contains datablock 4

CCDC references: 2119423; 2119422

Key indicators

Structure: 3
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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 [sigma](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

Computing details top

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]IZ = 2
Mr = 730.04F(000) = 672
Triclinic, P1Dx = 2.396 Mg m3
a = 8.4676 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8248 (3) ÅCell parameters from 47541 reflections
c = 14.0119 (5) Åθ = 2.7–36.4°
α = 76.374 (3)°µ = 12.74 mm1
β = 85.320 (2)°T = 100 K
γ = 85.251 (2)°Block, colourless
V = 1011.99 (6) Å30.09 × 0.06 × 0.05 mm
Data collection top
XtaLAB Synergy, HyPix
diffractometer
9374 independent reflections
Radiation source: micro-focus sealed X-ray tube8185 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.043
ω scansθmax = 36.7°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 1414
Tmin = 0.751, Tmax = 1.000k = 1414
84327 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-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 reflectionsΔρmax = 1.53 e Å3
203 parametersΔρmin = 2.02 e Å3
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
xyzUiso*/Ueq
Au10.46224 (2)0.71713 (2)0.23616 (2)0.01505 (2)
I10.25568 (2)0.12579 (2)0.72649 (2)0.01947 (3)
Br10.90742 (3)0.85910 (3)0.11585 (2)0.01837 (4)
Br20.22321 (3)0.27369 (3)0.58678 (2)0.02294 (5)
N10.7026 (2)0.8013 (2)0.06168 (14)0.0144 (3)
N20.4687 (2)0.7981 (2)0.01341 (14)0.0151 (3)
N30.3414 (2)0.4840 (2)0.41402 (14)0.0158 (3)
N40.3267 (2)0.7110 (2)0.44721 (14)0.0168 (3)
C10.5490 (3)0.7807 (3)0.09487 (17)0.0152 (4)
C20.7156 (3)0.8303 (3)0.03991 (16)0.0150 (4)
C30.5681 (3)0.8289 (3)0.07101 (17)0.0159 (4)
H30.5394320.8456250.1370050.019*
C40.8329 (3)0.7876 (3)0.12682 (17)0.0190 (4)
H4A0.7963280.8356650.1825300.023*
H4B0.9223920.8457730.0900370.023*
C50.8904 (3)0.6186 (3)0.1667 (2)0.0268 (5)
H5A0.8022770.5606580.2033770.040*
H5B0.9759850.6145180.2104550.040*
H5C0.9302490.5716160.1118320.040*
C60.3003 (3)0.7693 (3)0.01381 (19)0.0190 (4)
H6A0.2510330.8457110.0410040.023*
H6B0.2446480.7839810.0762500.023*
C70.2815 (3)0.6044 (3)0.0029 (2)0.0253 (5)
H7A0.3358130.5901230.0591520.038*
H7B0.1684250.5880030.0029060.038*
H7C0.3281320.5286990.0579820.038*
C80.3723 (3)0.6350 (3)0.37528 (17)0.0164 (4)
C90.2739 (3)0.4672 (3)0.50878 (17)0.0175 (4)
C100.2644 (3)0.6105 (3)0.53014 (17)0.0190 (4)
H100.2232330.6361190.5899020.023*
C110.3707 (3)0.3610 (3)0.35936 (19)0.0208 (4)
H11A0.3801370.2580810.4063760.025*
H11B0.4724520.3760790.3192890.025*
C120.2385 (4)0.3624 (3)0.2928 (2)0.0292 (6)
H12A0.1375550.3482280.3322230.044*
H12B0.2604130.2771900.2586000.044*
H12C0.2319930.4625110.2443250.044*
C130.3265 (3)0.8808 (3)0.43601 (19)0.0204 (4)
H13A0.4075230.9237640.3838010.024*
H13B0.3543810.9031980.4983250.024*
C140.1657 (4)0.9582 (3)0.4096 (3)0.0367 (7)
H14A0.1408980.9409890.3460400.055*
H14B0.1663271.0706070.4052800.055*
H14C0.0851560.9133490.4603900.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01531 (4)0.01589 (4)0.01371 (4)0.00177 (3)0.00196 (3)0.00363 (3)
I10.02119 (7)0.02104 (7)0.01555 (6)0.00120 (5)0.00096 (5)0.00454 (5)
Br10.01523 (10)0.02506 (11)0.01603 (9)0.00645 (8)0.00254 (7)0.00658 (8)
Br20.03080 (13)0.02037 (11)0.01701 (10)0.00987 (9)0.00213 (9)0.00004 (8)
N10.0136 (8)0.0164 (8)0.0137 (8)0.0021 (6)0.0003 (6)0.0045 (6)
N20.0129 (8)0.0163 (8)0.0155 (8)0.0007 (6)0.0000 (6)0.0031 (7)
N30.0170 (8)0.0159 (8)0.0149 (8)0.0017 (7)0.0007 (6)0.0040 (7)
N40.0204 (9)0.0153 (8)0.0148 (8)0.0032 (7)0.0003 (7)0.0035 (7)
C10.0139 (9)0.0155 (9)0.0165 (9)0.0023 (7)0.0017 (7)0.0046 (7)
C20.0152 (9)0.0172 (9)0.0128 (8)0.0035 (7)0.0011 (7)0.0038 (7)
C30.0149 (9)0.0178 (10)0.0153 (9)0.0021 (7)0.0001 (7)0.0045 (8)
C40.0176 (10)0.0256 (11)0.0157 (9)0.0056 (8)0.0020 (8)0.0070 (8)
C50.0241 (12)0.0309 (14)0.0253 (12)0.0050 (10)0.0074 (10)0.0065 (10)
C60.0119 (9)0.0231 (11)0.0217 (10)0.0001 (8)0.0017 (8)0.0049 (9)
C70.0201 (11)0.0243 (12)0.0330 (13)0.0066 (9)0.0003 (10)0.0081 (10)
C80.0153 (9)0.0167 (9)0.0169 (9)0.0016 (7)0.0004 (7)0.0036 (8)
C90.0211 (10)0.0171 (10)0.0136 (9)0.0045 (8)0.0012 (8)0.0011 (8)
C100.0218 (11)0.0199 (10)0.0151 (9)0.0047 (8)0.0014 (8)0.0037 (8)
C110.0251 (12)0.0174 (10)0.0212 (11)0.0008 (9)0.0005 (9)0.0075 (9)
C120.0391 (16)0.0252 (13)0.0264 (13)0.0052 (11)0.0088 (11)0.0085 (10)
C130.0271 (12)0.0143 (10)0.0200 (10)0.0054 (8)0.0024 (9)0.0042 (8)
C140.0328 (16)0.0179 (12)0.056 (2)0.0019 (11)0.0004 (14)0.0034 (13)
Geometric parameters (Å, º) top
Au1—C12.020 (2)C13—C141.506 (4)
Au1—C82.022 (2)C3—H30.9500
I1—Br1i3.5294 (3)C4—H4A0.9900
I1—Br23.6072 (3)C4—H4B0.9900
Au1—Br2ii3.8033 (3)C5—H5A0.9800
Br1—C21.869 (2)C5—H5B0.9800
Br2—C91.861 (2)C5—H5C0.9800
N1—C11.357 (3)C6—H6A0.9900
N1—C21.382 (3)C6—H6B0.9900
N1—C41.468 (3)C7—H7A0.9800
N2—C11.348 (3)C7—H7B0.9800
N2—C31.381 (3)C7—H7C0.9800
N2—C61.468 (3)C10—H100.9500
N3—C81.354 (3)C11—H11A0.9900
N3—C91.382 (3)C11—H11B0.9900
N3—C111.464 (3)C12—H12A0.9800
N4—C81.351 (3)C12—H12B0.9800
N4—C101.381 (3)C12—H12C0.9800
N4—C131.469 (3)C13—H13A0.9900
C2—C31.357 (3)C13—H13B0.9900
C4—C51.518 (4)C14—H14A0.9800
C6—C71.521 (4)C14—H14B0.9800
C9—C101.361 (3)C14—H14C0.9800
C11—C121.512 (4)
C1—Au1—C8174.97 (9)C4—C5—H5A109.5
Br1i—I1—Br2101.436 (8)C4—C5—H5B109.5
C2—Br1—I1iii172.43 (7)H5A—C5—H5B109.5
C9—Br2—I1162.21 (8)C4—C5—H5C109.5
C1—N1—C2109.82 (19)H5A—C5—H5C109.5
C1—N1—C4123.48 (19)H5B—C5—H5C109.5
C2—N1—C4126.65 (19)N2—C6—H6A109.5
C1—N2—C3111.61 (19)C7—C6—H6A109.5
C1—N2—C6124.54 (19)N2—C6—H6B109.5
C3—N2—C6123.46 (19)C7—C6—H6B109.5
C8—N3—C9110.15 (19)H6A—C6—H6B108.1
C8—N3—C11123.4 (2)C6—C7—H7A109.5
C9—N3—C11126.4 (2)C6—C7—H7B109.5
C8—N4—C10111.1 (2)H7A—C7—H7B109.5
C8—N4—C13124.9 (2)C6—C7—H7C109.5
C10—N4—C13123.7 (2)H7A—C7—H7C109.5
N2—C1—N1105.25 (19)H7B—C7—H7C109.5
N2—C1—Au1127.11 (16)C9—C10—H10127.0
N1—C1—Au1127.41 (17)N4—C10—H10127.0
C3—C2—N1107.77 (19)N3—C11—H11A109.3
C3—C2—Br1128.16 (17)C12—C11—H11A109.3
N1—C2—Br1124.05 (17)N3—C11—H11B109.3
C2—C3—N2105.6 (2)C12—C11—H11B109.3
N1—C4—C5112.1 (2)H11A—C11—H11B108.0
N2—C6—C7110.9 (2)C11—C12—H12A109.5
N4—C8—N3105.41 (19)C11—C12—H12B109.5
N4—C8—Au1130.27 (17)H12A—C12—H12B109.5
N3—C8—Au1124.30 (17)C11—C12—H12C109.5
C10—C9—N3107.3 (2)H12A—C12—H12C109.5
C10—C9—Br2130.48 (18)H12B—C12—H12C109.5
N3—C9—Br2122.09 (17)N4—C13—H13A109.5
C9—C10—N4106.0 (2)C14—C13—H13A109.5
N3—C11—C12111.5 (2)N4—C13—H13B109.5
N4—C13—C14110.6 (2)C14—C13—H13B109.5
C2—C3—H3127.2H13A—C13—H13B108.1
N2—C3—H3127.2C13—C14—H14A109.5
N1—C4—H4A109.2C13—C14—H14B109.5
C5—C4—H4A109.2H14A—C14—H14B109.5
N1—C4—H4B109.2C13—C14—H14C109.5
C5—C4—H4B109.2H14A—C14—H14C109.5
H4A—C4—H4B107.9H14B—C14—H14C109.5
C3—N2—C1—N10.2 (3)C13—N4—C8—N3175.0 (2)
C6—N2—C1—N1173.2 (2)C10—N4—C8—Au1177.04 (18)
C3—N2—C1—Au1174.55 (17)C13—N4—C8—Au13.3 (4)
C6—N2—C1—Au11.5 (3)C9—N3—C8—N41.3 (3)
C2—N1—C1—N20.3 (2)C11—N3—C8—N4178.8 (2)
C4—N1—C1—N2178.1 (2)C9—N3—C8—Au1177.17 (17)
C2—N1—C1—Au1174.36 (16)C11—N3—C8—Au10.4 (3)
C4—N1—C1—Au13.4 (3)C8—N3—C9—C100.8 (3)
C1—N1—C2—C30.4 (3)C11—N3—C9—C10178.3 (2)
C4—N1—C2—C3178.1 (2)C8—N3—C9—Br2177.42 (17)
C1—N1—C2—Br1177.92 (17)C11—N3—C9—Br25.1 (3)
C4—N1—C2—Br10.2 (3)I1—Br2—C9—C10114.8 (3)
N1—C2—C3—N20.3 (3)I1—Br2—C9—N361.0 (4)
Br1—C2—C3—N2177.95 (17)N3—C9—C10—N40.0 (3)
C1—N2—C3—C20.1 (3)Br2—C9—C10—N4176.24 (19)
C6—N2—C3—C2173.1 (2)C8—N4—C10—C90.8 (3)
C1—N1—C4—C581.0 (3)C13—N4—C10—C9174.6 (2)
C2—N1—C4—C596.4 (3)C8—N3—C11—C1280.8 (3)
C1—N2—C6—C794.9 (3)C9—N3—C11—C1296.4 (3)
C3—N2—C6—C777.4 (3)C8—N4—C13—C1494.0 (3)
C10—N4—C8—N31.3 (3)C10—N4—C13—C1479.0 (3)
Symmetry codes: (i) x1, y1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···I1iv0.953.153.966 (2)145
C4—H4A···I1ii0.993.103.995 (3)151
C6—H6A···I1iv0.993.213.955 (3)134
C10—H10···I1v0.953.203.993 (2)142
C11—H11A···Br20.992.793.265 (3)110
C11—H11B···I1vi0.993.193.903 (3)130
C12—H12B···Br1vii0.983.063.831 (3)137
C13—H13B···I1v0.993.194.053 (3)146
Symmetry codes: (ii) x+1, y+1, z+1; (iv) x, y+1, z1; (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]I2Z = 1
Mr = 1713.88F(000) = 778
Triclinic, P1Dx = 2.607 Mg m3
a = 8.0245 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5782 (3) ÅCell parameters from 24546 reflections
c = 15.9814 (6) Åθ = 2.6–34.1°
α = 91.228 (3)°µ = 13.23 mm1
β = 96.517 (4)°T = 100 K
γ = 92.255 (4)°Plate, brown
V = 1091.77 (8) Å30.08 × 0.03 × 0.01 mm
Data collection top
XtaLAB Synergy, HyPix
diffractometer
6378 independent reflections
Radiation source: micro-focus sealed X-ray tube5409 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.048
ω scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 1111
Tmin = 0.703, Tmax = 1.000k = 1212
61886 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-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 reflectionsΔρmax = 3.97 e Å3
215 parametersΔρmin = 2.66 e Å3
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
xyzUiso*/Ueq
Au10.5000000.5000000.0000000.01890 (8)
I10.36292 (6)0.37952 (6)0.12916 (3)0.02666 (11)
Br10.00401 (10)0.09434 (9)0.21316 (5)0.02965 (16)
N10.2548 (7)0.2807 (7)0.1082 (4)0.0227 (11)
N20.1732 (7)0.5172 (7)0.1164 (4)0.0218 (11)
C10.2957 (9)0.4283 (8)0.0806 (4)0.0199 (12)
C20.1053 (9)0.2781 (8)0.1624 (4)0.0236 (13)
C30.0556 (9)0.4261 (8)0.1680 (4)0.0242 (13)
H30.0411940.4612330.2008900.029*
C40.3602 (10)0.1472 (8)0.0908 (5)0.0282 (15)
H4A0.4260980.1633770.0348720.034*
H4B0.2873890.0517850.0887760.034*
C50.4806 (13)0.1229 (11)0.1572 (6)0.042 (2)
H5A0.5480690.2193050.1621280.064*
H5B0.5548160.0382870.1403290.064*
H5C0.4159910.0955970.2116600.064*
C60.1643 (9)0.6878 (8)0.1038 (4)0.0243 (13)
H6A0.2762040.7380500.1077830.029*
H6B0.0845600.7287860.1490170.029*
C70.1087 (11)0.7291 (10)0.0196 (5)0.0343 (17)
H7A0.1942480.6998220.0254030.051*
H7B0.0934450.8417520.0157930.051*
H7C0.0023210.6728100.0135350.051*
Au21.0000001.0000000.5000000.02101 (9)
I20.18002 (6)0.24488 (5)0.30519 (3)0.02377 (10)
Br20.40896 (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)
H3'0.3934970.9681820.3622030.026*
C4'0.8021 (9)0.6466 (8)0.4567 (4)0.0224 (13)
H4'10.7256340.5553490.4632110.027*
H4'20.8736720.6658330.5109050.027*
C5'0.9122 (10)0.6105 (8)0.3881 (5)0.0290 (15)
H5'10.8418010.5936540.3341520.044*
H5'20.9735150.5161800.4020160.044*
H5'30.9923380.6983540.3837580.044*
C6'0.6523 (10)1.1916 (8)0.4105 (5)0.0259 (14)
H6'10.7467731.2351490.4505020.031*
H6'20.5479691.2380370.4250630.031*
C7'0.6810 (9)1.2344 (8)0.3214 (5)0.0281 (15)
H7'10.7852741.1899450.3072540.042*
H7'20.6896631.3482790.3174760.042*
H7'30.5867041.1927420.2818330.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.02247 (17)0.01893 (16)0.01489 (15)0.00122 (12)0.00110 (12)0.00024 (12)
I10.0288 (2)0.0301 (2)0.0214 (2)0.00043 (18)0.00418 (16)0.00327 (17)
Br10.0348 (4)0.0248 (3)0.0272 (3)0.0053 (3)0.0026 (3)0.0047 (3)
N10.025 (3)0.023 (3)0.020 (3)0.000 (2)0.004 (2)0.002 (2)
N20.022 (3)0.021 (3)0.021 (3)0.002 (2)0.001 (2)0.003 (2)
C10.028 (3)0.018 (3)0.013 (3)0.002 (2)0.002 (2)0.001 (2)
C20.028 (3)0.024 (3)0.018 (3)0.004 (3)0.001 (2)0.003 (2)
C30.028 (3)0.027 (3)0.017 (3)0.000 (3)0.000 (2)0.004 (2)
C40.039 (4)0.019 (3)0.025 (3)0.001 (3)0.000 (3)0.002 (3)
C50.051 (5)0.035 (4)0.042 (5)0.004 (4)0.014 (4)0.008 (4)
C60.028 (3)0.021 (3)0.024 (3)0.001 (3)0.002 (3)0.000 (3)
C70.042 (5)0.031 (4)0.031 (4)0.005 (3)0.005 (3)0.007 (3)
Au20.02690 (18)0.01581 (16)0.01892 (16)0.00103 (12)0.00311 (13)0.00180 (12)
I20.0231 (2)0.0219 (2)0.0252 (2)0.00092 (15)0.00093 (16)0.00113 (16)
Br20.0266 (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—C1i2.033 (7)N2'—C6'1.459 (9)
Au1—C12.033 (7)C2'—C3'1.353 (9)
Au1—I1i2.6564 (5)C4'—C5'1.519 (10)
Au1—I12.6564 (5)C6'—C7'1.519 (11)
I1—I2ii3.5136 (7)C3—H30.9500
Br1—C21.870 (7)C4—H4A0.9900
Br1—I23.4347 (8)C4—H4B0.9900
N1—C11.347 (8)C5—H5A0.9800
N1—C21.397 (9)C5—H5B0.9800
N1—C41.464 (10)C5—H5C0.9800
N2—C11.351 (9)C6—H6A0.9900
N2—C31.385 (8)C6—H6B0.9900
N2—C61.479 (9)C7—H7A0.9800
C2—C31.348 (10)C7—H7B0.9800
C4—C51.530 (12)C7—H7C0.9800
C6—C71.504 (11)C3'—H3'0.9500
Au2—C1'2.018 (7)C4'—H4'10.9900
Au2—C1'iii2.018 (7)C4'—H4'20.9900
I2—Br23.5575 (8)C5'—H5'10.9800
I2—Au1ii4.1539 (5)C5'—H5'20.9800
Br2—C2'1.871 (7)C5'—H5'30.9800
N1'—C1'1.360 (8)C6'—H6'10.9900
N1'—C2'1.383 (9)C6'—H6'20.9900
N1'—C4'1.469 (8)C7'—H7'10.9800
N2'—C1'1.354 (9)C7'—H7'20.9800
N2'—C3'1.386 (9)C7'—H7'30.9800
C1i—Au1—C1180.0N2—C3—H3126.7
C1i—Au1—I1i90.95 (18)N1—C4—H4A109.1
C1—Au1—I1i89.05 (18)C5—C4—H4A109.1
C1i—Au1—I189.05 (18)N1—C4—H4B109.1
C1—Au1—I190.95 (18)C5—C4—H4B109.1
I1i—Au1—I1180.0H4A—C4—H4B107.8
Au1—I1—I2ii176.29 (2)C4—C5—H5A109.5
C2—Br1—I2179.5 (2)C4—C5—H5B109.5
C1—N1—C2109.5 (6)H5A—C5—H5B109.5
C1—N1—C4124.8 (6)C4—C5—H5C109.5
C2—N1—C4125.3 (6)H5A—C5—H5C109.5
C1—N2—C3110.4 (6)H5B—C5—H5C109.5
C1—N2—C6125.6 (6)N2—C6—H6A109.3
C3—N2—C6124.0 (6)C7—C6—H6A109.3
N1—C1—N2106.2 (6)N2—C6—H6B109.3
N1—C1—Au1126.4 (5)C7—C6—H6B109.3
N2—C1—Au1127.4 (5)H6A—C6—H6B107.9
C3—C2—N1107.2 (6)C6—C7—H7A109.5
C3—C2—Br1129.9 (6)C6—C7—H7B109.5
N1—C2—Br1122.9 (5)H7A—C7—H7B109.5
C2—C3—N2106.6 (6)C6—C7—H7C109.5
N1—C4—C5112.6 (7)H7A—C7—H7C109.5
N2—C6—C7111.8 (6)H7B—C7—H7C109.5
C1'—Au2—C1'iii180.0C2'—C3'—H3'127.0
Br1—I2—I1ii97.240 (19)N2'—C3'—H3'127.0
Br1—I2—Br2169.87 (2)N1'—C4'—H4'1109.3
I1ii—I2—Br272.852 (17)C5'—C4'—H4'1109.3
Br1—I2—Au2iv74.604 (16)N1'—C4'—H4'2109.3
I1ii—I2—Au2iv168.488 (16)C5'—C4'—H4'2109.3
Br2—I2—Au2iv114.871 (16)H4'1—C4'—H4'2108.0
C2'—Br2—I2177.0 (2)C4'—C5'—H5'1109.5
C1'—N1'—C2'110.4 (6)C4'—C5'—H5'2109.5
C1'—N1'—C4'123.3 (6)H5'1—C5'—H5'2109.5
C2'—N1'—C4'126.1 (6)C4'—C5'—H5'3109.5
C1'—N2'—C3'111.4 (6)H5'1—C5'—H5'3109.5
C1'—N2'—C6'124.9 (6)H5'2—C5'—H5'3109.5
C3'—N2'—C6'123.3 (6)N2'—C6'—H6'1109.4
N2'—C1'—N1'104.7 (6)C7'—C6'—H6'1109.4
N2'—C1'—Au2128.9 (5)N2'—C6'—H6'2109.4
N1'—C1'—Au2126.4 (5)C7'—C6'—H6'2109.4
C3'—C2'—N1'107.4 (6)H6'1—C6'—H6'2108.0
C3'—C2'—Br2128.7 (5)C6'—C7'—H7'1109.5
N1'—C2'—Br2123.9 (5)C6'—C7'—H7'2109.5
C2'—C3'—N2'105.9 (6)H7'1—C7'—H7'2109.5
N1'—C4'—C5'111.4 (6)C6'—C7'—H7'3109.5
N2'—C6'—C7'111.0 (6)H7'1—C7'—H7'3109.5
C2—C3—H3126.7H7'2—C7'—H7'3109.5
C2—N1—C1—N20.4 (7)C3'—N2'—C1'—N1'0.4 (8)
C4—N1—C1—N2174.5 (6)C6'—N2'—C1'—N1'173.8 (6)
C2—N1—C1—Au1179.8 (5)C3'—N2'—C1'—Au2178.6 (5)
C4—N1—C1—Au16.2 (10)C6'—N2'—C1'—Au25.3 (10)
C3—N2—C1—N11.0 (8)C2'—N1'—C1'—N2'0.4 (7)
C6—N2—C1—N1179.5 (6)C4'—N1'—C1'—N2'176.4 (6)
C3—N2—C1—Au1179.7 (5)C2'—N1'—C1'—Au2178.8 (5)
C6—N2—C1—Au10.2 (10)C4'—N1'—C1'—Au22.7 (9)
C1—N1—C2—C30.3 (8)C1'—N1'—C2'—C3'0.1 (8)
C4—N1—C2—C3173.8 (7)C4'—N1'—C2'—C3'176.1 (6)
C1—N1—C2—Br1179.1 (5)C1'—N1'—C2'—Br2178.1 (5)
C4—N1—C2—Br16.8 (10)C4'—N1'—C2'—Br22.2 (9)
N1—C2—C3—N20.9 (8)N1'—C2'—C3'—N2'0.1 (8)
Br1—C2—C3—N2178.5 (5)Br2—C2'—C3'—N2'178.3 (5)
C1—N2—C3—C21.2 (8)C1'—N2'—C3'—C2'0.4 (8)
C6—N2—C3—C2179.3 (6)C6'—N2'—C3'—C2'173.8 (6)
C1—N1—C4—C589.5 (8)C1'—N1'—C4'—C5'79.6 (8)
C2—N1—C4—C583.7 (9)C2'—N1'—C4'—C5'95.8 (8)
C1—N2—C6—C776.1 (9)C1'—N2'—C6'—C7'97.4 (8)
C3—N2—C6—C7104.5 (8)C3'—N2'—C6'—C7'75.2 (9)
Symmetry codes: (i) x1, y1, z; (ii) x, y, z; (iii) x+2, y+2, z+1; (iv) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···I1v0.953.283.913 (7)126
C3—H3···I2vi0.953.224.011 (7)142
C4—H4A···I10.993.284.002 (7)132
C6—H6A···I1i0.993.163.925 (7)136
C6—H6B···I2vi0.993.114.064 (7)163
C7—H7C···I1v0.983.294.051 (9)136
C3—H3···I2vii0.953.083.916 (7)148
C4—H42···I2viii0.993.103.883 (7)137
C7—H71···I2ix0.983.194.039 (7)146
Symmetry codes: (i) x1, y1, z; (v) x, y1, z; (vi) x, y1, z; (vii) x, y+1, z; (viii) x+1, y+1, z+1; (ix) x+1, y+1, z.
 

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