Potassium 3-formyl-[1,1′-biphen­yl]-4-olate monohydrate

Moriwaki, R.; Haraguchi, T.; Akitsu, T.

doi:10.1107/S2414314617013542

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 9| September 2017| x171354

https://doi.org/10.1107/S2414314617013542

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Potassium 3-formyl-[1,1′-biphenyl]-4-olate monohydrate

Ryoji Moriwaki,^a Tomoyuki Haraguchi ^a and Takashiro Akitsu ^a ^*

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
^*Correspondence e-mail: akitsu@rs.kagu.tus.ac.jp

Edited by O. Blacque, University of Zürich, Switzerland (Received 14 September 2017; accepted 21 September 2017; online 26 September 2017)

The title salt, K⁺·C₁₃H₉O₂⁻·H₂O, was synthesized from 5-bromosalicylaldehyde and a phenylboronic acid derivative using the Suzuki–Miyaura cross-coupling reaction (Miyaura & Suzuki, 1979 ). In addition to the intermolecular interactions between the charged species, two O—H⋯O hydrogen bonds involving the isolated water molecules further stabilize the crystal packing of the title salt leading to the formation of a three-dimensional framework structure.

Keywords: crystal structure; cross coupling reactions; potassium cation.

CCDC reference: 1575889

Structure description

Biaryl is an important basic skeleton for various kinds of molecules: physiologically active substances (e.g. diflunisal, which shows analgesic and anti-inflammatory action) and liquid crystals (e.g. 4-alkyl 4′-cyanobiphenyl). In addition, phenylphenol comprising a biaryl skeleton, is used as reagent, reactant (Kikushima & Nishina, 2013 ; Hall et al., 2017 ; Yuan et al., 2017 ) and drug (Jiratthiya et al. 2015 ).

In the crystal structure of the title compound (Fig. 1), the O atom of the formyl group is tilted towards the phenoxide O atom: the torsion angle C10—C9—C13—O2 is 3.0 (2)° and the torsion angle O2—C13—C9—C8 is −179.71 (13)°. The K⁺ cations are surrounded by seven O atoms from three isolated water molecules and three different [C₁₃H₉O₂]⁻ anions. The seven K⋯O distances are in the range of 2.717 (1)–2.960 (1) Å. Two O—H⋯O hydrogen bonds (Table 1) involving the isolated water molecules further stabilize the crystal packing of the title salt (Fig. 2) leading to the formation of a three-dimensional framework structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H14⋯O1ⁱ	0.82 (3)	1.96 (3)	2.7751 (15)	168 (2)
O3—H15⋯O1	0.86 (2)	1.87 (2)	2.7136 (15)	168 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
A packing diagram of the title compound.

Synthesis and crystallization

Treatment of 5-bromosalicylaldehyde (0.402 g, 2.00 mmol), phenylboronic acid (0.366 g, 3.00 mmol), K₂CO₃ (0.553 g, 4.00 mmol) and Pd(PPh₃)₄ (0.5 mol%) in EtOH–H₂O (4:1 v/v) for 5 h at 353 K in degassed N₂ (Morris & Nguyen, 2001 ) gave rise to a yellow precursor after evaporation and was dried in a desiccator for several days (68% yield). This crude yellow compound was filtered off and recrystallized by slow evaporation from a methanol solution to give yellow prismatic single crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The formyl H atom and the water H atoms were located and freely refined, while the other aromatic H atoms were placed in calculated positions.

Table 2
Experimental details

Crystal data
Chemical formula	K⁺·C₁₃H₉O₂⁻·HO
M_r	254.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	103
a, b, c (Å)	23.213 (5), 6.7398 (15), 7.2711 (16)
β (°)	90.593 (3)
V (Å³)	1137.5 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.46
Crystal size (mm)	0.27 × 0.18 × 0.10

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.886, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	5890, 2532, 2402
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.12
No. of reflections	2532
No. of parameters	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1575889

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617013542/zq4024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617013542/zq4024Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Potassium 3-formyl-[1,1'-biphenyl]-4-olate monohydrate top

Crystal data top

K⁺·C₁₃H₉O₂⁻·HO	F(000) = 528
M_r = 254.32	D_x = 1.485 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.213 (5) Å	Cell parameters from 4464 reflections
b = 6.7398 (15) Å	θ = 1.8–27.5°
c = 7.2711 (16) Å	µ = 0.46 mm⁻¹
β = 90.593 (3)°	T = 103 K
V = 1137.5 (4) Å³	Prism, orange
Z = 4	0.27 × 0.18 × 0.10 mm

Data collection top

Bruker APEXII diffractometer	2532 independent reflections
Radiation source: fine-focus sealed tube	2402 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.024
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −18→29
T_min = 0.886, T_max = 0.957	k = −7→8
5890 measured reflections	l = −9→8

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)] = 0.029	Hydrogen site location: mixed
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0255P)² + 0.8435P] where P = (F_o² + 2F_c²)/3
2532 reflections	(Δ/σ)_max = 0.001
170 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 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	U_iso*/U_eq
O1	0.59348 (4)	0.52653 (14)	0.58043 (13)	0.0108 (2)
O3	0.53358 (4)	0.72835 (16)	0.83869 (14)	0.0128 (2)
O2	0.61886 (4)	0.43723 (15)	0.20229 (13)	0.0127 (2)
C10	0.64935 (6)	0.52030 (19)	0.59788 (18)	0.0095 (3)
C12	0.73524 (6)	0.5543 (2)	0.79525 (18)	0.0115 (3)
H12	0.7511	0.5843	0.913	0.014*
C11	0.67639 (6)	0.5623 (2)	0.77061 (19)	0.0115 (3)
C9	0.68751 (6)	0.4706 (2)	0.45135 (18)	0.0099 (3)
C8	0.74752 (6)	0.4621 (2)	0.48228 (19)	0.0111 (3)
H8	0.7717	0.4267	0.3828	0.013*
C7	0.77284 (6)	0.5032 (2)	0.65162 (19)	0.0108 (3)
C13	0.66859 (6)	0.4365 (2)	0.26244 (19)	0.0112 (3)
C6	0.83627 (6)	0.4996 (2)	0.68178 (19)	0.0118 (3)
C5	0.86217 (6)	0.6294 (2)	0.8087 (2)	0.0150 (3)
H5	0.8389	0.7199	0.875	0.018*
C1	0.87173 (6)	0.3692 (2)	0.5851 (2)	0.0151 (3)
H1	0.8551	0.2796	0.4987	0.018*
C4	0.92142 (6)	0.6274 (2)	0.8388 (2)	0.0174 (3)
H4	0.9382	0.7151	0.9265	0.021*
C3	0.95605 (6)	0.4978 (2)	0.7413 (2)	0.0178 (3)
H3	0.9966	0.4968	0.7613	0.021*
C2	0.93100 (7)	0.3692 (2)	0.6139 (2)	0.0182 (3)
H2	0.9546	0.2809	0.5461	0.022*
H11	0.6529 (7)	0.601 (3)	0.873 (2)	0.015 (4)*
H13	0.7009 (7)	0.408 (3)	0.178 (2)	0.012 (4)*
H14	0.5538 (10)	0.807 (4)	0.897 (3)	0.040 (7)*
H15	0.5545 (9)	0.680 (3)	0.753 (3)	0.027 (5)*
K1	0.55412 (2)	0.31194 (4)	0.91130 (4)	0.01045 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0090 (5)	0.0120 (5)	0.0113 (4)	0.0002 (4)	0.0007 (3)	−0.0005 (4)
O3	0.0108 (5)	0.0155 (5)	0.0122 (5)	−0.0005 (4)	0.0019 (4)	−0.0030 (4)
O2	0.0127 (5)	0.0142 (5)	0.0111 (5)	−0.0022 (4)	−0.0012 (4)	0.0005 (4)
C10	0.0120 (6)	0.0056 (6)	0.0109 (6)	−0.0008 (5)	0.0005 (5)	0.0011 (5)
C12	0.0152 (7)	0.0104 (6)	0.0088 (6)	−0.0013 (5)	−0.0015 (5)	−0.0003 (5)
C11	0.0137 (7)	0.0112 (6)	0.0097 (6)	−0.0005 (5)	0.0022 (5)	−0.0008 (5)
C9	0.0125 (6)	0.0075 (6)	0.0097 (6)	−0.0008 (5)	0.0008 (5)	0.0005 (5)
C8	0.0118 (6)	0.0102 (6)	0.0115 (6)	−0.0001 (5)	0.0028 (5)	−0.0006 (5)
C7	0.0113 (6)	0.0085 (6)	0.0126 (6)	−0.0007 (5)	0.0001 (5)	0.0007 (5)
C13	0.0133 (7)	0.0094 (6)	0.0109 (6)	−0.0012 (5)	0.0023 (5)	0.0002 (5)
C6	0.0120 (7)	0.0124 (6)	0.0110 (6)	−0.0003 (5)	0.0000 (5)	0.0025 (5)
C5	0.0146 (7)	0.0152 (7)	0.0153 (7)	−0.0002 (6)	0.0012 (5)	−0.0025 (6)
C1	0.0156 (7)	0.0158 (7)	0.0140 (7)	0.0013 (6)	−0.0013 (5)	−0.0022 (6)
C4	0.0154 (7)	0.0201 (7)	0.0166 (7)	−0.0032 (6)	−0.0015 (6)	−0.0021 (6)
C3	0.0105 (7)	0.0239 (8)	0.0192 (7)	0.0007 (6)	−0.0019 (5)	0.0026 (6)
C2	0.0166 (7)	0.0202 (7)	0.0178 (7)	0.0046 (6)	0.0017 (6)	−0.0013 (6)
K1	0.01107 (15)	0.01123 (15)	0.00905 (15)	0.00107 (11)	0.00014 (10)	−0.00008 (11)

Geometric parameters (Å, º) top

O1—C10	1.3026 (17)	C7—C6	1.4864 (19)
O1—K1ⁱ	2.7437 (11)	C13—K1ⁱ	3.3310 (15)
O1—K1	2.9597 (11)	C13—H13	0.992 (17)
O3—K1ⁱⁱ	2.7567 (11)	C6—C1	1.399 (2)
O3—K1ⁱⁱⁱ	2.7730 (12)	C6—C5	1.402 (2)
O3—K1	2.8943 (13)	C5—C4	1.391 (2)
O3—H14	0.82 (3)	C5—H5	0.95
O3—H15	0.86 (2)	C1—C2	1.390 (2)
O2—C13	1.2302 (17)	C1—H1	0.95
O2—K1^iv	2.7170 (11)	C4—C3	1.387 (2)
O2—K1ⁱ	2.7268 (11)	C4—H4	0.95
C10—C11	1.4266 (19)	C3—C2	1.391 (2)
C10—C9	1.4324 (19)	C3—H3	0.95
C10—K1ⁱ	3.4175 (14)	C2—H2	0.95
C10—K1	3.4866 (14)	K1—O2^v	2.7171 (11)
C12—C11	1.377 (2)	K1—O2^vi	2.7269 (11)
C12—C7	1.4107 (19)	K1—O1^vi	2.7437 (11)
C12—H12	0.95	K1—O3ⁱⁱ	2.7566 (11)
C11—K1	3.4656 (15)	K1—O3^vii	2.7730 (12)
C11—H11	0.962 (18)	K1—C13^vi	3.3311 (15)
C9—C8	1.4098 (19)	K1—C10^vi	3.4175 (14)
C9—C13	1.4561 (19)	K1—K1^vi	3.7302 (8)
C8—C7	1.3869 (19)	K1—H11	3.022 (18)
C8—H8	0.95	K1—H15	2.74 (2)

C10—O1—K1ⁱ	110.09 (8)	O1^vi—K1—O3	160.29 (3)
C10—O1—K1	102.74 (8)	O3ⁱⁱ—K1—O3	95.42 (3)
K1ⁱ—O1—K1	81.60 (3)	O3^vii—K1—O3	87.65 (2)
K1ⁱⁱ—O3—K1ⁱⁱⁱ	84.84 (3)	O2^v—K1—O1	107.95 (3)
K1ⁱⁱ—O3—K1	84.58 (3)	O2^vi—K1—O1	70.82 (3)
K1ⁱⁱⁱ—O3—K1	115.79 (4)	O1^vi—K1—O1	131.80 (4)
K1ⁱⁱ—O3—H14	98.1 (16)	O3ⁱⁱ—K1—O1	145.13 (3)
K1ⁱⁱⁱ—O3—H14	128.3 (16)	O3^vii—K1—O1	78.29 (3)
K1—O3—H14	115.9 (16)	O3—K1—O1	55.22 (3)
K1ⁱⁱ—O3—H15	150.4 (14)	O2^v—K1—C13^vi	88.43 (4)
K1ⁱⁱⁱ—O3—H15	90.9 (14)	O2^vi—K1—C13^vi	20.48 (3)
K1—O3—H15	71.0 (14)	O1^vi—K1—C13^vi	57.63 (3)
H14—O3—H15	107 (2)	O3ⁱⁱ—K1—C13^vi	139.62 (4)
C13—O2—K1^iv	141.72 (9)	O3^vii—K1—C13^vi	105.52 (4)
C13—O2—K1ⁱ	108.66 (8)	O3—K1—C13^vi	123.96 (3)
K1^iv—O2—K1ⁱ	86.51 (3)	O1—K1—C13^vi	74.19 (3)
O1—C10—C11	120.53 (12)	O2^v—K1—C10^vi	62.89 (3)
O1—C10—C9	123.92 (12)	O2^vi—K1—C10^vi	57.30 (3)
C11—C10—C9	115.55 (12)	O1^vi—K1—C10^vi	20.97 (3)
O1—C10—K1ⁱ	48.94 (6)	O3ⁱⁱ—K1—C10^vi	98.79 (4)
C11—C10—K1ⁱ	139.15 (9)	O3^vii—K1—C10^vi	126.48 (3)
C9—C10—K1ⁱ	87.36 (8)	O3—K1—C10^vi	144.33 (3)
O1—C10—K1	55.89 (6)	O1—K1—C10^vi	116.04 (3)
C11—C10—K1	77.33 (8)	C13^vi—K1—C10^vi	44.33 (3)
C9—C10—K1	142.48 (9)	O2^v—K1—C11	68.31 (3)
K1ⁱ—C10—K1	65.40 (3)	O2^vi—K1—C11	71.19 (3)
C11—C12—C7	122.26 (12)	O1^vi—K1—C11	105.50 (3)
C11—C12—H12	118.9	O3ⁱⁱ—K1—C11	148.79 (3)
C7—C12—H12	118.9	O3^vii—K1—C11	120.22 (4)
C12—C11—C10	122.25 (13)	O3—K1—C11	66.92 (3)
C12—C11—K1	139.20 (9)	O1—K1—C11	42.39 (3)
C10—C11—K1	78.99 (8)	C13^vi—K1—C11	59.36 (4)
C12—C11—H11	118.6 (10)	C10^vi—K1—C11	84.71 (4)
C10—C11—H11	119.1 (10)	O2^v—K1—C10	91.98 (3)
K1—C11—H11	55.2 (11)	O2^vi—K1—C10	61.77 (3)
C8—C9—C10	120.56 (12)	O1^vi—K1—C10	114.67 (3)
C8—C9—C13	115.60 (12)	O3ⁱⁱ—K1—C10	161.48 (3)
C10—C9—C13	123.75 (12)	O3^vii—K1—C10	96.86 (4)
C7—C8—C9	122.86 (13)	O3—K1—C10	66.08 (3)
C7—C8—H8	118.6	O1—K1—C10	21.37 (3)
C9—C8—H8	118.6	C13^vi—K1—C10	58.45 (3)
C8—C7—C12	116.50 (12)	C10^vi—K1—C10	96.40 (4)
C8—C7—C6	122.53 (12)	C11—K1—C10	23.68 (3)
C12—C7—C6	120.95 (12)	O2^v—K1—K1^vi	46.86 (2)
O2—C13—C9	127.42 (13)	O2^vi—K1—K1^vi	114.26 (3)
O2—C13—K1ⁱ	50.86 (7)	O1^vi—K1—K1^vi	51.71 (2)
C9—C13—K1ⁱ	90.38 (8)	O3ⁱⁱ—K1—K1^vi	47.76 (2)
O2—C13—H13	119.7 (10)	O3^vii—K1—K1^vi	125.88 (3)
C9—C13—H13	112.9 (10)	O3—K1—K1^vi	113.15 (2)
K1ⁱ—C13—H13	135.7 (10)	O1—K1—K1^vi	154.79 (2)
C1—C6—C5	118.17 (13)	C13^vi—K1—K1^vi	102.25 (3)
C1—C6—C7	121.55 (13)	C10^vi—K1—K1^vi	58.19 (2)
C5—C6—C7	120.28 (13)	C11—K1—K1^vi	113.89 (2)
C4—C5—C6	120.96 (14)	C10—K1—K1^vi	137.19 (2)
C4—C5—H5	119.5	O2^v—K1—H11	57.2 (3)
C6—C5—H5	119.5	O2^vi—K1—H11	85.5 (4)
C2—C1—C6	120.73 (14)	O1^vi—K1—H11	109.1 (3)
C2—C1—H1	119.6	O3ⁱⁱ—K1—H11	133.7 (4)
C6—C1—H1	119.6	O3^vii—K1—H11	128.5 (3)
C3—C4—C5	120.20 (14)	O3—K1—H11	58.8 (3)
C3—C4—H4	119.9	O1—K1—H11	50.9 (3)
C5—C4—H4	119.9	C13^vi—K1—H11	71.6 (3)
C4—C3—C2	119.47 (14)	C10^vi—K1—H11	88.3 (3)
C4—C3—H3	120.3	C11—K1—H11	15.2 (3)
C2—C3—H3	120.3	C10—K1—H11	36.3 (3)
C1—C2—C3	120.46 (14)	K1^vi—K1—H11	104.0 (3)
C1—C2—H2	119.8	O2^v—K1—H15	92.4 (4)
C3—C2—H2	119.8	O2^vi—K1—H15	108.6 (5)
O2^v—K1—O2^vi	108.77 (4)	O1^vi—K1—H15	160.1 (4)
O2^v—K1—O1^vi	74.36 (3)	O3ⁱⁱ—K1—H15	111.9 (5)
O2^vi—K1—O1^vi	63.57 (3)	O3^vii—K1—H15	85.0 (4)
O2^v—K1—O3ⁱⁱ	85.61 (4)	O3—K1—H15	17.2 (5)
O2^vi—K1—O3ⁱⁱ	136.21 (3)	O1—K1—H15	38.0 (5)
O1^vi—K1—O3ⁱⁱ	82.37 (3)	C13^vi—K1—H15	108.3 (5)
O2^v—K1—O3^vii	165.93 (3)	C10^vi—K1—H15	139.2 (4)
O2^vi—K1—O3^vii	85.10 (3)	C11—K1—H15	55.1 (4)
O1^vi—K1—O3^vii	111.33 (3)	C10—K1—H15	49.8 (5)
O3ⁱⁱ—K1—O3^vii	82.54 (3)	K1^vi—K1—H15	127.9 (5)
O2^v—K1—O3	85.95 (3)	H11—K1—H15	51.1 (5)
O2^vi—K1—O3	125.89 (3)

K1ⁱ—O1—C10—C11	−130.61 (11)	C13—C9—C8—C7	175.89 (13)
K1—O1—C10—C11	−45.02 (13)	C9—C8—C7—C12	0.2 (2)
K1ⁱ—O1—C10—C9	48.75 (14)	C9—C8—C7—C6	−178.19 (13)
K1—O1—C10—C9	134.34 (11)	C11—C12—C7—C8	0.4 (2)
K1—O1—C10—K1ⁱ	85.59 (5)	C11—C12—C7—C6	178.84 (13)
K1ⁱ—O1—C10—K1	−85.59 (5)	K1^iv—O2—C13—C9	−161.18 (10)
C7—C12—C11—C10	−0.3 (2)	K1ⁱ—O2—C13—C9	−52.27 (16)
C7—C12—C11—K1	112.39 (15)	K1^iv—O2—C13—K1ⁱ	−108.92 (14)
O1—C10—C11—C12	178.99 (12)	C8—C9—C13—O2	−179.71 (13)
C9—C10—C11—C12	−0.42 (19)	C10—C9—C13—O2	−3.0 (2)
K1ⁱ—C10—C11—C12	117.93 (14)	C8—C9—C13—K1ⁱ	142.45 (11)
K1—C10—C11—C12	142.10 (13)	C10—C9—C13—K1ⁱ	−40.80 (13)
O1—C10—C11—K1	36.89 (11)	C8—C7—C6—C1	−32.3 (2)
C9—C10—C11—K1	−142.53 (11)	C12—C7—C6—C1	149.29 (14)
K1ⁱ—C10—C11—K1	−24.17 (12)	C8—C7—C6—C5	147.29 (14)
O1—C10—C9—C8	−178.37 (12)	C12—C7—C6—C5	−31.1 (2)
C11—C10—C9—C8	1.02 (19)	C1—C6—C5—C4	−0.5 (2)
K1ⁱ—C10—C9—C8	−143.79 (12)	C7—C6—C5—C4	179.81 (13)
K1—C10—C9—C8	−101.90 (16)	C5—C6—C1—C2	−0.2 (2)
O1—C10—C9—C13	5.0 (2)	C7—C6—C1—C2	179.40 (13)
C11—C10—C9—C13	−175.58 (13)	C6—C5—C4—C3	0.8 (2)
K1ⁱ—C10—C9—C13	39.61 (13)	C5—C4—C3—C2	−0.3 (2)
K1—C10—C9—C13	81.51 (19)	C6—C1—C2—C3	0.7 (2)
C10—C9—C8—C7	−1.0 (2)	C4—C3—C2—C1	−0.4 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x, y, z−1; (v) x, y, z+1; (vi) x, −y+1/2, z+1/2; (vii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H14···O1^viii	0.82 (3)	1.96 (3)	2.7751 (15)	168 (2)
O3—H15···O1	0.86 (2)	1.87 (2)	2.7136 (15)	168 (2)

Symmetry code: (viii) x, −y+3/2, z+1/2.

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