Crystal structures of the isotypic complexes bis­(morpholine)­gold(I) chloride and bis­(morpholine)­gold(I) bromide

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...halide contacts lead to a layer structure.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.015
• wR factor = 0.026
• Data-to-parameter ratio = 24.9

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.015
• wR factor = 0.026
• Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.50 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..CL1      .       2.92 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H16A     ..CL1      .       2.91 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13B     ..O14      .       2.65 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15A     ..O14      .       2.61 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         81 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.50 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..BR1      .       2.94 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H16A     ..BR1      .       2.98 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13B     ..O14      .       2.70 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15A     ..O14      .       2.61 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Bis(morpholine-κN)gold(I) chloride (1)

Crystal data

[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) Å^3	Block, colourless
Z = 4	0.08 × 0.08 × 0.03 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.015	Hydrogen site location: mixed
wR(F^2) = 0.026	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0016P)^2 + 3.0402P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Au1—N11	2.0631 (19)	C12—H12A	0.9900
Au1—N11^i	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—N11^i	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)

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···Cl1^ii	0.99	2.92	3.836 (2)	154
C16—H16A···Cl1^iii	0.99	2.91	3.654 (2)	132
C13—H13B···O14^iv	0.99	2.65	3.511 (3)	146
C15—H15A···O14^v	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)

Crystal data

[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) Å^3	Block, colourless
Z = 4	0.08 × 0.05 × 0.05 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.026	w = 1/[σ^2(Fo^2) + (0.0064P)^2 + 1.529P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00023 (3)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Au1—N11^i	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)
N11^i—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)

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···Br1^ii	0.99	2.94	3.860 (2)	155
C16—H16A···Br1^iii	0.99	2.98	3.717 (2)	132
C13—H13B···O14^iv	0.99	2.70	3.542 (3)	144
C15—H15A···O14^v	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.