Asymmetric hydrogen bonds in centrosymmetric environment. II. Neutron study of very short hydrogen bonds in potassium hydrogen dichloromaleate at 90 K and 170 K

Olovsson, I.; Ptasiewicz-Bak, H.; Gustafsson, T.; Majerz, I.

doi:10.1107/S0108768102004858

Asymmetric hydrogen bonds in centrosymmetric environment. II. Neutron study of very short hydrogen bonds in potassium hydrogen dichloromaleate at 90 K and 170 K

I. Olovsson, H. Ptasiewicz-Bak, T. Gustafsson and I. Majerz

In our earlier neutron diffraction study of the title compound at 30 K and 295 K an unconventional strategy in the refinement of hydrogen was applied and the same procedure has now been followed in the present investigation at 170 K and 90 K. There are two short O

O hydrogen bonds [2.437 (2) Å and 2.442 (2) Å at 30 K] and the `heavy-atom' structure is centrosymmetric (P $\bar1$ ) with centres of symmetry in the middle of the O

O bonds. However, statistical significance tests clearly show that an asymmetric location of both H atoms gives the most satisfactory description of the structure at all temperatures. The shift of hydrogen from the centre of symmetry is 0.15, 0.14, 0.15 and 0.15 Å for H2 at 30, 90, 170 and 295 K, respectively, and 0.15, 0.15, 0.15 and 0.12 Å for H4 (σ = 0.01 Å). Furthermore, the behaviour of H2 is very interesting: at 295 K and 170 K it is located on one side of the symmetry centre but at 90 K and 30 K it is located on the other side. A detailed determination of the unit-cell parameters by X-ray diffraction in the whole temperature range from 30 K to 295 K has revealed that the data points of the cell parameters as a function of temperature fall on two different straight lines with a sudden change in the slope around 135 K. It appears likely that the change in the location of H2 as the temperature is lowered is related to this behaviour. At 170 K, R(F) = 0.029 for 1236 reflections; at 90 K, R(F) = 0.030 for 1457 reflections.

Keywords: asymmetric hydrogen bonds; hydrogen bonds; potassium hydrogen dichloromaleate.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102004858/os0089sup1.cif Contains datablocks text, 1, 2
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768102004858/os00891sup2.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768102004858/os00892sup3.sft Supplementary material

CCDC references: 193575; 193576

Comment top

%T {βf (Comment section to be typeset from manuscript)}

Computing details top

For both compounds, data collection: Aracor Diffractometer Control Program; cell refinement: STOE 4-circle X-ray Diffractometer Control Program; data reduction: ARACOR-DATRED vers. 950320; program(s) used to refine structure: UPALS Lundgren (1982).

Figures top

%T {βf (Figure captions to be typeset from manuscript)}

(1) top

Crystal data top

K₂Cl₄O₈C₈H₂	γ = 89.35 (5)°
M_r = 446.1	V = 344.6 (3) Å³
Triclinic, P1	Z = 1
Hall symbol: P 1	D_x = 2.150 Mg m⁻³
a = 5.048 (3) Å	Neutron radiation, λ = 1.207 Å
b = 7.840 (4) Å	µ = 0.09 mm⁻¹
c = 8.839 (4) Å	T = 170 K
α = 81.46 (5)°	Plate with 6 faces, colourless
β = 85.05 (5)°	4.2 × 3.5 × 1.0 mm

Data collection top

Huber-Aracor 400 mm diameter four-circle diffractometer	R_int = 0.036
θ–2θ scans	θ_max = 52°
Absorption correction: numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)	h = 0→6
T_min = 0.700, T_max = 0.917	k = −10→10
1614 measured reflections	l = −11→11
1370 independent reflections	3 standard reflections every 33 reflections
1236 reflections with F_o² > 3σ(F_o²)	intensity decay: stable

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.055	(Δ/σ)_max = 0.05
wR(F²) = 0.075	Δρ_max = 0.04 e Å⁻³
S = 1.01	Δρ_min = −0.04 e Å⁻³
1236 reflections	Extinction correction: Lorentzian type I isotropic (Becker & Coppens, 1974, 1975)
119 parameters	Extinction coefficient: 6580.1

Crystal data top

K₂Cl₄O₈C₈H₂	γ = 89.35 (5)°
M_r = 446.1	V = 344.6 (3) Å³
Triclinic, P1	Z = 1
a = 5.048 (3) Å	Neutron radiation, λ = 1.207 Å
b = 7.840 (4) Å	µ = 0.09 mm⁻¹
c = 8.839 (4) Å	T = 170 K
α = 81.46 (5)°	4.2 × 3.5 × 1.0 mm
β = 85.05 (5)°

Data collection top

Huber-Aracor 400 mm diameter four-circle diffractometer	1236 reflections with F_o² > 3σ(F_o²)
Absorption correction: numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)	R_int = 0.036
T_min = 0.700, T_max = 0.917	3 standard reflections every 33 reflections
1614 measured reflections	intensity decay: stable
1370 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	119 parameters
wR(F²) = 0.075	All H-atom parameters refined
S = 1.01	Δρ_max = 0.04 e Å⁻³
1236 reflections	Δρ_min = −0.04 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
K	0.3011 (3)	−0.1556 (2)	0.6239 (2)	0.0159 (8)
Cl1	0.4700 (1)	−0.2461 (1)	0.0585 (1)	0.0152 (3)
Cl2	0.1324 (1)	−0.5711 (1)	0.2016 (1)	0.0188 (4)
O1	0.2357 (2)	−0.0033 (1)	0.3337 (1)	0.0173 (5)
O2	0.0261 (2)	0.0490 (1)	0.1226 (1)	0.0148 (5)
O3	−0.2501 (2)	−0.2209 (1)	0.4020 (1)	0.0159 (5)
O4	−0.2980 (2)	−0.5061 (1)	0.4144 (1)	0.0157 (5)
C1	0.1506 (2)	−0.0507 (1)	0.2213 (1)	0.0103 (4)
C2	0.2011 (2)	−0.2330 (1)	0.1886 (1)	0.0096 (4)
C3	0.0552 (2)	−0.3717 (1)	0.2514 (1)	0.0105 (4)
C4	−0.1824 (2)	−0.3610 (1)	0.3652 (1)	0.0106 (4)
H2	0.0250 (19)	0.0074 (15)	−0.0042 (12)	0.022 (2)
H4	−0.494 (2)	−0.5036 (14)	0.5163 (8)	0.0201 (19)
K1	−0.3011 (3)	0.1556 (2)	−0.6239 (2)	0.0159 (8)
Cl11	−0.4700 (1)	0.2461 (1)	−0.0585 (1)	0.0152 (3)
Cl21	−0.1324 (1)	0.5711 (1)	−0.2016 (1)	0.0188 (4)
O11	−0.2357 (2)	0.0033 (1)	−0.3337 (1)	0.0173 (5)
O21	−0.0261 (2)	−0.0490 (1)	−0.1226 (1)	0.0148 (5)
O31	0.2501 (2)	0.2209 (1)	−0.4020 (1)	0.0159 (5)
O41	0.2980 (2)	0.5061 (1)	−0.4144 (1)	0.0157 (5)
C11	−0.1506 (2)	0.0507 (1)	−0.2213 (1)	0.0103 (4)
C21	−0.2011 (2)	0.2330 (1)	−0.1886 (1)	0.0096 (4)
C31	−0.0552 (2)	0.3717 (1)	−0.2514 (1)	0.0105 (4)
C41	0.1824 (2)	0.3610 (1)	−0.3652 (1)	0.0106 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K	0.0176 (8)	0.0115 (7)	0.0185 (8)	−0.0017 (6)	0.0023 (6)	−0.0037 (6)
Cl1	0.0121 (3)	0.0170 (3)	0.0166 (3)	0.0005 (3)	0.0061 (2)	−0.0023 (2)
Cl2	0.0204 (4)	0.0097 (3)	0.0263 (4)	0.0007 (3)	0.0104 (2)	−0.0066 (2)
O1	0.0182 (6)	0.0163 (5)	0.0174 (5)	0.0006 (4)	−0.0064 (4)	−0.0076 (4)
O2	0.0205 (5)	0.0102 (5)	0.0137 (5)	0.0036 (4)	−0.0035 (4)	−0.0025 (4)
O3	0.0164 (5)	0.0104 (5)	0.0209 (5)	0.0008 (4)	0.0073 (4)	−0.0047 (4)
O4	0.0138 (5)	0.0109 (5)	0.0225 (5)	−0.0018 (3)	0.0089 (4)	−0.0039 (4)
C1	0.0104 (4)	0.0089 (4)	0.0115 (4)	−0.0003 (3)	−0.0006 (3)	−0.0027 (3)
C2	0.0086 (4)	0.0086 (4)	0.0115 (4)	0.0001 (3)	0.0012 (3)	−0.0021 (3)
C3	0.0100 (3)	0.0080 (4)	0.0134 (4)	−0.0001 (3)	0.0033 (3)	−0.0022 (3)
C4	0.0094 (4)	0.0088 (4)	0.0136 (4)	0.0001 (3)	0.0031 (3)	−0.0024 (3)
H2	0.013 (3)	0.0162 (19)	0.0361 (17)	−0.0078 (19)	0.0018 (19)	0.0016 (13)
H4	0.0312 (16)	0.0188 (14)	0.010 (3)	−0.0024 (12)	−0.003 (2)	−0.001 (2)
K1	0.0176 (8)	0.0115 (7)	0.0185 (8)	−0.0017 (6)	0.0023 (6)	−0.0037 (6)
Cl11	0.0121 (3)	0.0170 (3)	0.0166 (3)	0.0005 (3)	0.0061 (2)	−0.0023 (2)
Cl21	0.0204 (4)	0.0097 (3)	0.0263 (4)	0.0007 (3)	0.0104 (2)	−0.0066 (2)
O11	0.0182 (6)	0.0163 (5)	0.0174 (5)	0.0006 (4)	−0.0064 (4)	−0.0076 (4)
O21	0.0205 (5)	0.0102 (5)	0.0137 (5)	0.0036 (4)	−0.0035 (4)	−0.0025 (4)
O31	0.0164 (5)	0.0104 (5)	0.0209 (5)	0.0008 (4)	0.0073 (4)	−0.0047 (4)
O41	0.0138 (5)	0.0109 (5)	0.0225 (5)	−0.0018 (3)	0.0089 (4)	−0.0039 (4)
C11	0.0104 (4)	0.0089 (4)	0.0115 (4)	−0.0003 (3)	−0.0006 (3)	−0.0027 (3)
C21	0.0086 (4)	0.0086 (4)	0.0115 (4)	0.0001 (3)	0.0012 (3)	−0.0021 (3)
C31	0.0100 (3)	0.0080 (4)	0.0134 (4)	−0.0001 (3)	0.0033 (3)	−0.0022 (3)
C41	0.0094 (4)	0.0088 (4)	0.0136 (4)	0.0001 (3)	0.0031 (3)	−0.0024 (3)

Geometric parameters (Å, º) top

K—O1	2.710 (2)	C1—C2	1.515 (1)
K—O41ⁱ	2.723 (2)	C2—C3	1.342 (1)
Cl1—C2	1.714 (1)	C3—C4	1.508 (1)
Cl2—C3	1.718 (1)	O2—H2	1.214 (11)
O1—C1	1.224 (1)	O21—H2	1.243 (11)
O2—C1	1.283 (1)	O4—H4	1.282 (10)
O3—C4	1.228 (1)	O41ⁱⁱ—H4	1.175 (11)
O4—C4	1.283 (1)

O1—C1—O2	123.4 (1)	C2—C3—C4	122.5 (1)
O1—C1—C2	120.1 (1)	C3—C4—O3	119.7 (1)
O2—C1—C2	116.4 (1)	C3—C4—O4	114.3 (1)
C1—C2—C3	125.3 (1)	O3—C4—O4	125.9 (1)
C1—C2—Cl1	112.5 (1)	H2—O2—C1	116.8 (5)
Cl1—C2—C3	122.3 (1)	H2—O21—C11	117.7 (5)
C2—C3—Cl2	120.4 (1)	H4—O4—C4	116.2 (5)
Cl2—C3—C4	117.1 (1)	H4ⁱⁱⁱ—O41—C41	114.9 (6)

Symmetry codes: (i) x, y−1, z+1; (ii) x−1, y−1, z+1; (iii) x+1, y+1, z−1.

(2) top

Crystal data top

K₂Cl₄O₈C₈H₂	γ = 89.16 (4)°
M_r = 446.1	V = 342.6 (2) Å³
Triclinic, P1	Z = 1
Hall symbol: P 1	D_x = 2.162 Mg m⁻³
a = 5.031 (3) Å	Neutron radiation, λ = 1.207 Å
b = 7.827 (4) Å	µ = 0.09 mm⁻¹
c = 8.835 (5) Å	T = 90 K
α = 81.24 (4)°	Plate with 6 faces, colourless
β = 85.17 (4)°	4.2 × 3.5 × 1.0 mm

Data collection top

Huber-Aracor 400 mm diameter four-circle diffractometer	R_int = 0.034
θ–2θ scans	θ_max = 52°
Absorption correction: numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)	h = 0→6
T_min = 0.702, T_max = 0.916	k = −10→10
1880 measured reflections	l = −11→11
1580 independent reflections	3 standard reflections every 33 reflections
1457 reflections with F_o² > 3σ(F_o²)	intensity decay: stable

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.054	(Δ/σ)_max = 0.05
wR(F²) = 0.080	Δρ_max = 0.04 e Å⁻³
S = 1.09	Δρ_min = −0.04 e Å⁻³
1457 reflections	Extinction correction: Lorentzian type I isotropic (Becker & Coppens, 1974, 1975)
119 parameters	Extinction coefficient: 7038.3

Crystal data top

K₂Cl₄O₈C₈H₂	γ = 89.16 (4)°
M_r = 446.1	V = 342.6 (2) Å³
Triclinic, P1	Z = 1
a = 5.031 (3) Å	Neutron radiation, λ = 1.207 Å
b = 7.827 (4) Å	µ = 0.09 mm⁻¹
c = 8.835 (5) Å	T = 90 K
α = 81.24 (4)°	4.2 × 3.5 × 1.0 mm
β = 85.17 (4)°

Data collection top

Huber-Aracor 400 mm diameter four-circle diffractometer	1457 reflections with F_o² > 3σ(F_o²)
Absorption correction: numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)	R_int = 0.034
T_min = 0.702, T_max = 0.916	3 standard reflections every 33 reflections
1880 measured reflections	intensity decay: stable
1580 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	119 parameters
wR(F²) = 0.080	All H-atom parameters refined
S = 1.09	Δρ_max = 0.04 e Å⁻³
1457 reflections	Δρ_min = −0.04 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
K	0.3018 (3)	−0.1558 (2)	0.6241 (2)	0.0100 (6)
Cl1	0.4732 (1)	−0.2449 (1)	0.0595 (1)	0.0097 (3)
Cl2	0.1359 (1)	−0.5712 (1)	0.2025 (1)	0.0125 (3)
O1	0.2353 (2)	−0.0021 (1)	0.3342 (1)	0.0112 (4)
O2	0.0253 (2)	0.0501 (1)	0.1220 (1)	0.0094 (4)
O3	−0.2506 (2)	−0.2205 (1)	0.4022 (1)	0.0101 (4)
O4	−0.2970 (2)	−0.5065 (1)	0.4149 (1)	0.0102 (4)
C1	0.1507 (1)	−0.0496 (1)	0.2216 (1)	0.0070 (3)
C2	0.2030 (1)	−0.2323 (1)	0.1893 (1)	0.0070 (3)
C3	0.0574 (1)	−0.3712 (1)	0.2522 (1)	0.0072 (3)
C4	−0.1818 (1)	−0.3605 (1)	0.3654 (1)	0.0070 (3)
H2	−0.0079 (18)	0.0095 (11)	−0.0148 (8)	0.0160 (11)
H4	−0.5221 (16)	−0.4924 (11)	0.5089 (9)	0.0175 (11)
K1	−0.3018 (3)	0.1558 (2)	−0.6241 (2)	0.0100 (6)
Cl11	−0.4732 (1)	0.2449 (1)	−0.0595 (1)	0.0097 (3)
Cl21	−0.1359 (1)	0.5712 (1)	−0.2025 (1)	0.0125 (3)
O11	−0.2353 (2)	0.0021 (1)	−0.3342 (1)	0.0112 (4)
O21	−0.0253 (2)	−0.0501 (1)	−0.1220 (1)	0.0094 (4)
O31	0.2506 (2)	0.2205 (1)	−0.4022 (1)	0.0101 (4)
O41	0.2970 (2)	0.5065 (1)	−0.4149 (1)	0.0102 (4)
C11	−0.1507 (1)	0.0496 (1)	−0.2216 (1)	0.0070 (3)
C21	−0.2030 (1)	0.2323 (1)	−0.1893 (1)	0.0070 (3)
C31	−0.0574 (1)	0.3712 (1)	−0.2522 (1)	0.0072 (3)
C41	0.1818 (1)	0.3605 (1)	−0.3654 (1)	0.0070 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K	0.0090 (6)	0.0090 (6)	0.0119 (6)	−0.0008 (5)	0.0014 (4)	−0.0014 (5)
Cl1	0.0071 (3)	0.0108 (3)	0.0110 (3)	0.0004 (2)	0.0038 (2)	−0.0013 (2)
Cl2	0.0128 (3)	0.0064 (2)	0.0164 (3)	0.0001 (2)	0.0058 (2)	−0.0037 (2)
O1	0.0116 (4)	0.0108 (4)	0.0111 (4)	0.0006 (3)	−0.0035 (3)	−0.0041 (3)
O2	0.0104 (4)	0.0080 (4)	0.0098 (4)	0.0014 (3)	−0.0022 (3)	−0.0010 (3)
O3	0.0095 (4)	0.0074 (4)	0.0135 (4)	−0.0001 (3)	0.0037 (3)	−0.0024 (3)
O4	0.0083 (4)	0.0081 (4)	0.0143 (4)	−0.0017 (3)	0.0046 (3)	−0.0019 (3)
C1	0.0066 (3)	0.0062 (3)	0.0081 (3)	−0.0004 (3)	−0.0007 (2)	−0.0011 (3)
C2	0.0062 (3)	0.0067 (3)	0.0082 (3)	−0.0001 (3)	0.0007 (3)	−0.0009 (3)
C3	0.0066 (3)	0.0058 (3)	0.0091 (3)	0.0002 (3)	0.0022 (2)	−0.0015 (3)
C4	0.0058 (3)	0.0064 (3)	0.0090 (3)	−0.0001 (3)	0.0019 (3)	−0.0013 (3)
H2	0.0225 (12)	0.0116 (10)	0.0138 (12)	0.0035 (9)	−0.0088 (9)	0.0088 (9)
H4	0.0165 (12)	0.0146 (10)	0.0215 (12)	0.0054 (9)	0.0084 (9)	−0.0102 (9)
K1	0.0090 (6)	0.0090 (6)	0.0119 (6)	−0.0008 (5)	0.0014 (4)	−0.0014 (5)
Cl11	0.0071 (3)	0.0108 (3)	0.0110 (3)	0.0004 (2)	0.0038 (2)	−0.0013 (2)
Cl21	0.0128 (3)	0.0064 (2)	0.0164 (3)	0.0001 (2)	0.0058 (2)	−0.0037 (2)
O11	0.0116 (4)	0.0108 (4)	0.0111 (4)	0.0006 (3)	−0.0035 (3)	−0.0041 (3)
O21	0.0104 (4)	0.0080 (4)	0.0098 (4)	0.0014 (3)	−0.0022 (3)	−0.0010 (3)
O31	0.0095 (4)	0.0074 (4)	0.0135 (4)	−0.0001 (3)	0.0037 (3)	−0.0024 (3)
O41	0.0083 (4)	0.0081 (4)	0.0143 (4)	−0.0017 (3)	0.0046 (3)	−0.0019 (3)
C11	0.0066 (3)	0.0062 (3)	0.0081 (3)	−0.0004 (3)	−0.0007 (2)	−0.0011 (3)
C21	0.0062 (3)	0.0067 (3)	0.0082 (3)	−0.0001 (3)	0.0007 (3)	−0.0009 (3)
C31	0.0066 (3)	0.0058 (3)	0.0091 (3)	0.0002 (3)	0.0022 (2)	−0.0015 (3)
C41	0.0058 (3)	0.0064 (3)	0.0090 (3)	−0.0001 (3)	0.0019 (3)	−0.0013 (3)

Geometric parameters (Å, º) top

K—O1	2.704 (2)	C1—C2	1.515 (1)
K—O41ⁱ	2.717 (2)	C2—C3	1.341 (1)
Cl1—C2	1.715 (1)	C3—C4	1.509 (1)
Cl2—C3	1.721 (1)	O2—H2	1.320 (7)
O1—C1	1.224 (1)	O21—H2	1.127 (8)
O2—C1	1.285 (1)	O4—H4	1.358 (8)
O3—C4	1.226 (1)	O41ⁱⁱ—H4	1.087 (8)
O4—C4	1.288 (1)

O1—C1—O2	123.5 (1)	C2—C3—C4	122.5 (1)
O1—C1—C2	120.2 (1)	C3—C4—O3	119.9 (1)
O2—C1—C2	116.3 (1)	C3—C4—O4	114.2 (1)
C1—C2—C3	125.2 (1)	O3—C4—O4	125.9 (1)
C1—C2—Cl1	112.5 (1)	H2—O2—C1	121.9 (4)
Cl1—C2—C3	122.4 (1)	H2—O21—C11	111.7 (4)
C2—C3—Cl2	120.3 (1)	H4—O4—C4	113.2 (4)
Cl2—C3—C4	117.2 (1)	H4ⁱⁱⁱ—O41—C41	118.3 (5)

Symmetry codes: (i) x, y−1, z+1; (ii) x−1, y−1, z+1; (iii) x+1, y+1, z−1.

Experimental details

	(1)	(2)
Crystal data
Chemical formula	K₂Cl₄O₈C₈H₂	K₂Cl₄O₈C₈H₂
M_r	446.1	446.1
Crystal system, space group	Triclinic, P1	Triclinic, P1
Temperature (K)	170	90
a, b, c (Å)	5.048 (3), 7.840 (4), 8.839 (4)	5.031 (3), 7.827 (4), 8.835 (5)
α, β, γ (°)	81.46 (5), 85.05 (5), 89.35 (5)	81.24 (4), 85.17 (4), 89.16 (4)
V (Å³)	344.6 (3)	342.6 (2)
Z	1	1
Radiation type	Neutron, λ = 1.207 Å	Neutron, λ = 1.207 Å
µ (mm⁻¹)	0.09	0.09
Crystal size (mm)	4.2 × 3.5 × 1.0	4.2 × 3.5 × 1.0

Data collection
Diffractometer	Huber-Aracor 400 mm diameter four-circle diffractometer	Huber-Aracor 400 mm diameter four-circle diffractometer
Absorption correction	Numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)	Numerical gaussian (Coppens, Leiserowitz & Rabinovich, 1965)
T_min, T_max	0.700, 0.917	0.702, 0.916
No. of measured, independent and observed [F_o² > 3σ(F_o²)] reflections	1614, 1370, 1236	1880, 1580, 1457
R_int	0.036	0.034
(sin θ/λ)_max (Å⁻¹)	0.653	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.075, 1.01	0.054, 0.080, 1.09
No. of reflections	1236	1457
No. of parameters	119	119
No. of restraints	?	?
H-atom treatment	All H-atom parameters refined	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.04, −0.04	0.04, −0.04

Computer programs: Aracor Diffractometer Control Program, STOE 4-circle X-ray Diffractometer Control Program, ARACOR-DATRED vers. 950320, UPALS Lundgren (1982).

Selected geometric parameters (Å, º) for (1) top

K—O1	2.710 (2)	C1—C2	1.515 (1)
K—O41ⁱ	2.723 (2)	C2—C3	1.342 (1)
Cl1—C2	1.714 (1)	C3—C4	1.508 (1)
Cl2—C3	1.718 (1)	O2—H2	1.214 (11)
O1—C1	1.224 (1)	O21—H2	1.243 (11)
O2—C1	1.283 (1)	O4—H4	1.282 (10)
O3—C4	1.228 (1)	O41ⁱⁱ—H4	1.175 (11)
O4—C4	1.283 (1)

O1—C1—O2	123.4 (1)	C2—C3—C4	122.5 (1)
O1—C1—C2	120.1 (1)	C3—C4—O3	119.7 (1)
O2—C1—C2	116.4 (1)	C3—C4—O4	114.3 (1)
C1—C2—C3	125.3 (1)	O3—C4—O4	125.9 (1)
C1—C2—Cl1	112.5 (1)	H2—O2—C1	116.8 (5)
Cl1—C2—C3	122.3 (1)	H2—O21—C11	117.7 (5)
C2—C3—Cl2	120.4 (1)	H4—O4—C4	116.2 (5)
Cl2—C3—C4	117.1 (1)	H4ⁱⁱⁱ—O41—C41	114.9 (6)

Symmetry codes: (i) x, y−1, z+1; (ii) x−1, y−1, z+1; (iii) x+1, y+1, z−1.

Selected geometric parameters (Å, º) for (2) top

K—O1	2.704 (2)	C1—C2	1.515 (1)
K—O41ⁱ	2.717 (2)	C2—C3	1.341 (1)
Cl1—C2	1.715 (1)	C3—C4	1.509 (1)
Cl2—C3	1.721 (1)	O2—H2	1.320 (7)
O1—C1	1.224 (1)	O21—H2	1.127 (8)
O2—C1	1.285 (1)	O4—H4	1.358 (8)
O3—C4	1.226 (1)	O41ⁱⁱ—H4	1.087 (8)
O4—C4	1.288 (1)

O1—C1—O2	123.5 (1)	C2—C3—C4	122.5 (1)
O1—C1—C2	120.2 (1)	C3—C4—O3	119.9 (1)
O2—C1—C2	116.3 (1)	C3—C4—O4	114.2 (1)
C1—C2—C3	125.2 (1)	O3—C4—O4	125.9 (1)
C1—C2—Cl1	112.5 (1)	H2—O2—C1	121.9 (4)
Cl1—C2—C3	122.4 (1)	H2—O21—C11	111.7 (4)
C2—C3—Cl2	120.3 (1)	H4—O4—C4	113.2 (4)
Cl2—C3—C4	117.2 (1)	H4ⁱⁱⁱ—O41—C41	118.3 (5)

Symmetry codes: (i) x, y−1, z+1; (ii) x−1, y−1, z+1; (iii) x+1, y+1, z−1.

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