In the title compounds, the gold atoms lie on inversion centres and are linearly coordinated by two morpholine ligands. The halide anions lie on twofold axes. Hydrogen bonds and Au
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halide contacts lead to a layer structure.
Supporting information
CCDC references: 2113955; 2113954
Bis(morpholine-
κN)gold(I) chloride (1)
top
Crystal data top
[Au(C4H9NO)2]Cl | F(000) = 768 |
Mr = 406.66 | Dx = 2.344 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.9504 (9) Å | Cell parameters from 7694 reflections |
b = 5.92161 (19) Å | θ = 2.4–30.8° |
c = 11.3049 (5) Å | µ = 12.98 mm−1 |
β = 114.729 (6)° | T = 100 K |
V = 1152.27 (10) Å3 | Block, colourless |
Z = 4 | 0.08 × 0.08 × 0.03 mm |
Data collection top
Oxford Diffraction Xcalibur, Eos diffractometer | 1744 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1440 reflections with I > 2σ(I) |
Detector resolution: 16.1419 pixels mm-1 | Rint = 0.036 |
ω scan | θmax = 30.9°, θmin = 2.4° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | h = −26→27 |
Tmin = 0.692, Tmax = 1.000 | k = −8→8 |
18488 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.015 | Hydrogen site location: mixed |
wR(F2) = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0016P)2 + 3.0402P] where P = (Fo2 + 2Fc2)/3 |
1744 reflections | (Δ/σ)max < 0.001 |
70 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Special details top
Geometry. Non-bonded contacts:
3.7187 (0.0005) Au1 - Cl1_$2
3.7187 (0.0005) Au1 - Cl1_$1 Dihedral angles:
180.00 ( 0.00) C12 - N11 - N11_$5 - C12_$5
56.59 ( 0.22) C16 - N11 - N11_$5 - C12_$5 Copntact angles:
93.91 ( 1.20) H01 - Cl1 - H01_$6
98.93 ( 0.02) Au1_$7 - Cl1 - Au1_$8
180.00 Cl1_$1 - Au1 - Cl1_$2 Symmetry operators: EQIV $1 -x+1, -y, -z+1
EQIV $2 x, y+1, z
EQIV $5 1-x,1-y,1-z
EQIV $6 1-x, y, 1.5-z
EQIV $7 x, -1+y, z
EQIV $8 x, -y, 0.5+z |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.500000 | 0.500000 | 0.500000 | 0.01184 (3) | |
Cl1 | 0.500000 | −0.09186 (14) | 0.750000 | 0.01674 (15) | |
N11 | 0.42478 (11) | 0.2880 (3) | 0.53588 (18) | 0.0123 (4) | |
H01 | 0.4520 (14) | 0.179 (4) | 0.583 (2) | 0.013 (6)* | |
C12 | 0.36225 (13) | 0.1930 (4) | 0.4149 (2) | 0.0154 (4) | |
H12A | 0.333280 | 0.074808 | 0.438030 | 0.018* | |
H12B | 0.385631 | 0.123171 | 0.360087 | 0.018* | |
C13 | 0.30752 (14) | 0.3799 (4) | 0.3402 (2) | 0.0159 (5) | |
H13A | 0.336351 | 0.492262 | 0.312681 | 0.019* | |
H13B | 0.265864 | 0.316043 | 0.260689 | 0.019* | |
O14 | 0.27328 (8) | 0.4903 (3) | 0.41568 (14) | 0.0164 (3) | |
C15 | 0.33247 (13) | 0.5800 (4) | 0.5321 (2) | 0.0147 (4) | |
H15A | 0.308067 | 0.654884 | 0.583911 | 0.018* | |
H15B | 0.362484 | 0.695237 | 0.509131 | 0.018* | |
C16 | 0.38698 (13) | 0.3975 (4) | 0.6133 (2) | 0.0133 (4) | |
H16A | 0.427037 | 0.464101 | 0.693674 | 0.016* | |
H16B | 0.357640 | 0.283561 | 0.638690 | 0.016* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.01025 (5) | 0.01374 (5) | 0.01282 (5) | 0.00112 (5) | 0.00610 (4) | 0.00242 (5) |
Cl1 | 0.0190 (4) | 0.0122 (3) | 0.0155 (4) | 0.000 | 0.0037 (3) | 0.000 |
N11 | 0.0111 (9) | 0.0126 (9) | 0.0139 (9) | 0.0037 (8) | 0.0059 (8) | 0.0035 (7) |
C12 | 0.0174 (11) | 0.0133 (11) | 0.0162 (11) | −0.0020 (9) | 0.0077 (10) | −0.0026 (9) |
C13 | 0.0166 (11) | 0.0185 (12) | 0.0133 (11) | −0.0020 (9) | 0.0068 (10) | −0.0021 (9) |
O14 | 0.0120 (7) | 0.0227 (8) | 0.0139 (7) | 0.0029 (7) | 0.0049 (6) | 0.0017 (7) |
C15 | 0.0157 (11) | 0.0164 (10) | 0.0130 (10) | 0.0028 (9) | 0.0069 (9) | −0.0003 (9) |
C16 | 0.0135 (11) | 0.0163 (11) | 0.0112 (10) | 0.0019 (9) | 0.0061 (9) | 0.0022 (9) |
Geometric parameters (Å, º) top
Au1—N11 | 2.0631 (19) | C12—H12A | 0.9900 |
Au1—N11i | 2.0631 (19) | C12—H12B | 0.9900 |
N11—C16 | 1.491 (3) | C13—H13A | 0.9900 |
N11—C12 | 1.495 (3) | C13—H13B | 0.9900 |
C12—C13 | 1.510 (3) | C15—H15A | 0.9900 |
C13—O14 | 1.429 (3) | C15—H15B | 0.9900 |
O14—C15 | 1.427 (3) | C16—H16A | 0.9900 |
C15—C16 | 1.511 (3) | C16—H16B | 0.9900 |
N11—H01 | 0.86 (3) | | |
| | | |
N11—Au1—N11i | 180.0 | H12A—C12—H12B | 108.2 |
C16—N11—C12 | 108.02 (17) | O14—C13—H13A | 109.2 |
C16—N11—Au1 | 113.07 (14) | C12—C13—H13A | 109.2 |
C12—N11—Au1 | 113.41 (13) | O14—C13—H13B | 109.2 |
N11—C12—C13 | 109.38 (18) | C12—C13—H13B | 109.2 |
O14—C13—C12 | 112.27 (18) | H13A—C13—H13B | 107.9 |
C15—O14—C13 | 110.06 (16) | O14—C15—H15A | 109.3 |
O14—C15—C16 | 111.59 (19) | C16—C15—H15A | 109.3 |
N11—C16—C15 | 109.17 (17) | O14—C15—H15B | 109.3 |
C16—N11—H01 | 105.9 (16) | C16—C15—H15B | 109.3 |
C12—N11—H01 | 109.0 (17) | H15A—C15—H15B | 108.0 |
Au1—N11—H01 | 107.0 (16) | N11—C16—H16A | 109.8 |
N11—C12—H12A | 109.8 | C15—C16—H16A | 109.8 |
C13—C12—H12A | 109.8 | N11—C16—H16B | 109.8 |
N11—C12—H12B | 109.8 | C15—C16—H16B | 109.8 |
C13—C12—H12B | 109.8 | H16A—C16—H16B | 108.3 |
| | | |
C16—N11—C12—C13 | 57.7 (2) | C13—O14—C15—C16 | −58.5 (2) |
Au1—N11—C12—C13 | −68.44 (19) | C12—N11—C16—C15 | −58.7 (2) |
N11—C12—C13—O14 | −58.2 (2) | Au1—N11—C16—C15 | 67.7 (2) |
C12—C13—O14—C15 | 57.7 (2) | O14—C15—C16—N11 | 60.0 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H01···Cl1 | 0.86 (3) | 2.35 (3) | 3.172 (2) | 160 (2) |
C12—H12B···Cl1ii | 0.99 | 2.92 | 3.836 (2) | 154 |
C16—H16A···Cl1iii | 0.99 | 2.91 | 3.654 (2) | 132 |
C13—H13B···O14iv | 0.99 | 2.65 | 3.511 (3) | 146 |
C15—H15A···O14v | 0.99 | 2.61 | 3.439 (3) | 142 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x+1/2, −y+3/2, −z+1. |
Bis(morpholine-
κN)gold(I) bromide (2)
top
Crystal data top
[Au(C4H9NO)2]Br | F(000) = 840 |
Mr = 451.12 | Dx = 2.519 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.8719 (6) Å | Cell parameters from 8239 reflections |
b = 6.07840 (17) Å | θ = 3.5–30.5° |
c = 11.4050 (4) Å | µ = 15.71 mm−1 |
β = 114.595 (4)° | T = 100 K |
V = 1189.57 (7) Å3 | Block, colourless |
Z = 4 | 0.08 × 0.05 × 0.05 mm |
Data collection top
Oxford Diffraction Xcalibur, Eos diffractometer | 1739 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1601 reflections with I > 2σ(I) |
Detector resolution: 16.1419 pixels mm-1 | Rint = 0.042 |
ω scan | θmax = 30.0°, θmin = 2.4° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | h = −26→26 |
Tmin = 0.733, Tmax = 1.000 | k = −8→8 |
22827 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.015 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.026 | w = 1/[σ2(Fo2) + (0.0064P)2 + 1.529P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1739 reflections | Δρmax = 0.58 e Å−3 |
70 parameters | Δρmin = −0.64 e Å−3 |
0 restraints | Extinction correction: SHELXL-2019/3 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00023 (3) |
Special details top
Geometry. Non-bonded distances:
3.7686 (0.0002) Au1 - Br1_$2
3.7686 (0.0002) Au1 - Br1_$1 Pseudo torsion angles:
180.00 ( 0.00) C12 - N11 - N11_$5 - C12_$5
55.84 ( 0.21) C16 - N11 - N11_$5 - C12_$5 Contact angles:
93.29 ( 1.11) H01 - Br1 - H01_$6
98.33 ( 0.01) Au1_$7 - Br1 - Au1_$8
180.00 ( 0.00) Br1_$1 - Au1 - Br1_$2 Operators for generating equivalent atoms:
$1 -x+1, -y, -z+1
$2 x, y+1, z
$5 -x+1, -y+1, -z+1
$6 -x+1, y, -z+3/2
$8 x, -y, z+1/2 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.500000 | 0.500000 | 0.500000 | 0.01205 (4) | |
Br1 | 0.500000 | −0.09457 (5) | 0.750000 | 0.01529 (7) | |
N11 | 0.42269 (10) | 0.2957 (3) | 0.53179 (17) | 0.0124 (4) | |
H01 | 0.4507 (13) | 0.183 (4) | 0.578 (2) | 0.015* | |
C12 | 0.36012 (12) | 0.2040 (4) | 0.4122 (2) | 0.0153 (4) | |
H12A | 0.330978 | 0.088952 | 0.435159 | 0.018* | |
H12B | 0.383632 | 0.135900 | 0.357941 | 0.018* | |
C13 | 0.30529 (12) | 0.3856 (4) | 0.33819 (19) | 0.0154 (4) | |
H13A | 0.334174 | 0.494886 | 0.310626 | 0.018* | |
H13B | 0.263473 | 0.323130 | 0.259703 | 0.018* | |
O14 | 0.27109 (9) | 0.4933 (3) | 0.41320 (14) | 0.0163 (3) | |
C15 | 0.33036 (12) | 0.5800 (4) | 0.52921 (19) | 0.0148 (4) | |
H15A | 0.305701 | 0.652157 | 0.580629 | 0.018* | |
H15B | 0.360713 | 0.692559 | 0.507110 | 0.018* | |
C16 | 0.38456 (11) | 0.4011 (4) | 0.60869 (19) | 0.0130 (4) | |
H16A | 0.424643 | 0.464628 | 0.688740 | 0.016* | |
H16B | 0.354807 | 0.289658 | 0.632976 | 0.016* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.01062 (6) | 0.01299 (6) | 0.01400 (6) | 0.00095 (5) | 0.00659 (4) | 0.00242 (5) |
Br1 | 0.01822 (15) | 0.01134 (14) | 0.01438 (14) | 0.000 | 0.00487 (12) | 0.000 |
N11 | 0.0131 (9) | 0.0111 (9) | 0.0142 (9) | 0.0036 (7) | 0.0070 (7) | 0.0036 (7) |
C12 | 0.0175 (11) | 0.0129 (11) | 0.0165 (10) | −0.0027 (9) | 0.0079 (9) | −0.0040 (9) |
C13 | 0.0173 (11) | 0.0180 (12) | 0.0111 (10) | −0.0005 (9) | 0.0062 (8) | −0.0017 (9) |
O14 | 0.0121 (7) | 0.0216 (8) | 0.0146 (7) | 0.0032 (7) | 0.0049 (6) | 0.0006 (7) |
C15 | 0.0154 (10) | 0.0162 (10) | 0.0125 (10) | 0.0026 (9) | 0.0057 (8) | −0.0006 (9) |
C16 | 0.0120 (10) | 0.0173 (11) | 0.0110 (9) | 0.0011 (9) | 0.0060 (8) | 0.0012 (9) |
Geometric parameters (Å, º) top
Au1—N11i | 2.0598 (18) | C13—H13A | 0.9900 |
Au1—N11 | 2.0598 (18) | C13—H13B | 0.9900 |
N11—C16 | 1.491 (3) | O14—C15 | 1.431 (3) |
N11—C12 | 1.491 (3) | C15—C16 | 1.509 (3) |
N11—H01 | 0.89 (2) | C15—H15A | 0.9900 |
C12—C13 | 1.508 (3) | C15—H15B | 0.9900 |
C12—H12A | 0.9900 | C16—H16A | 0.9900 |
C12—H12B | 0.9900 | C16—H16B | 0.9900 |
C13—O14 | 1.427 (2) | | |
| | | |
N11i—Au1—N11 | 180.00 (7) | O14—C13—H13B | 109.2 |
C16—N11—C12 | 107.83 (16) | C12—C13—H13B | 109.2 |
C16—N11—Au1 | 113.28 (14) | H13A—C13—H13B | 107.9 |
C12—N11—Au1 | 114.42 (13) | C13—O14—C15 | 110.40 (15) |
C16—N11—H01 | 107.2 (15) | O14—C15—C16 | 111.31 (19) |
C12—N11—H01 | 107.6 (16) | O14—C15—H15A | 109.4 |
Au1—N11—H01 | 106.2 (15) | C16—C15—H15A | 109.4 |
N11—C12—C13 | 109.65 (18) | O14—C15—H15B | 109.4 |
N11—C12—H12A | 109.7 | C16—C15—H15B | 109.4 |
C13—C12—H12A | 109.7 | H15A—C15—H15B | 108.0 |
N11—C12—H12B | 109.7 | N11—C16—C15 | 109.18 (16) |
C13—C12—H12B | 109.7 | N11—C16—H16A | 109.8 |
H12A—C12—H12B | 108.2 | C15—C16—H16A | 109.8 |
O14—C13—C12 | 112.10 (17) | N11—C16—H16B | 109.8 |
O14—C13—H13A | 109.2 | C15—C16—H16B | 109.8 |
C12—C13—H13A | 109.2 | H16A—C16—H16B | 108.3 |
| | | |
C16—N11—C12—C13 | 58.0 (2) | C13—O14—C15—C16 | −58.2 (2) |
Au1—N11—C12—C13 | −68.99 (18) | C12—N11—C16—C15 | −59.1 (2) |
N11—C12—C13—O14 | −58.0 (2) | Au1—N11—C16—C15 | 68.54 (19) |
C12—C13—O14—C15 | 57.3 (2) | O14—C15—C16—N11 | 60.1 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H01···Br1 | 0.89 (2) | 2.46 (2) | 3.3056 (18) | 159.0 (19) |
C12—H12B···Br1ii | 0.99 | 2.94 | 3.860 (2) | 155 |
C16—H16A···Br1iii | 0.99 | 2.98 | 3.717 (2) | 132 |
C13—H13B···O14iv | 0.99 | 2.70 | 3.542 (3) | 144 |
C15—H15A···O14v | 0.99 | 2.61 | 3.446 (3) | 142 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x+1/2, −y+3/2, −z+1. |