(Quinoline-2-carboxyl­ato-κO)(quinoline-2-carb­oxy­lic acid-κO)bis­(quinoline-2-carb­oxy­lic acid-κ2N,O)potassium

Ng, S.W.

doi:10.1107/S1600536810027510

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m948

https://doi.org/10.1107/S1600536810027510

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(Quinoline-2-carboxylato-κO)(quinoline-2-carboxylic acid-κO)bis(quinoline-2-carboxylic acid-κ²N,O)potassium

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2010; accepted 11 July 2010; online 17 July 2010)

The K atom in the title complex, [K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃], lies on a twofold rotation axis that relates one N,O-chelating quinoline-2-carboxylic acid to the other; their N and O atoms are cis to each other in the distorted octahedral coordination geometry. The K atom is also coordinated by another monodentate quinoline-2-carboxylic acid; the acid is disordered with respect to a monodentate quinoline-2-carboxylate anion; the acid and anion are linked by an O—H⋯O hydrogen bond. An O—H⋯N hydrogen bond links adjacent molecules into a linear chain structure along the a axis.

Related literature

For the crystal structure of quinoline-2-carboxylic acid, see: Dobrzyńska & Jerzykiewicz (2004 ).

Experimental

Crystal data

[K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃]
M_r = 730.76
Orthorhombic, I b c a
a = 17.8679 (10) Å
b = 18.3617 (10) Å
c = 20.5162 (11) Å
V = 6731.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.24 × 0.08 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.991
40797 measured reflections
3888 independent reflections
3025 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.102
S = 1.01
3888 reflections
248 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2ⁱ	0.85 (1)	1.84 (1)	2.671 (2)	167 (2)
O3—H3⋯O3ⁱⁱ	0.84 (1)	1.62 (1)	2.452 (2)	175 (6)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027510/jh2182sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027510/jh2182Isup2.hkl

checkCIF report

Comment top

Quinoline-2-carboxylic acid exists as a 1:1 co-crystal of neutral quinoline-2-carboxylic acid and zwitterionic quinolinium-2-carboxylate, the two components being held together by O–H···O [2.566 (2) Å] and N–H···O [2.685 (2), 2.739 (2) Å] hydrogen bonds (Dobrzyńska & Jerzykiewicz, 2004). The potassium derivative formally exists as a co-crystal with three molecules of quinoline-2-carboxylic acid (Scheme I); however, the crystal structure is better interpreted in terms of the potassium atom being bis-N,O-chelated by two neutral acid molecules, and being coordinated by a third acid along with a carboxylate anion (Fig. 1); O–H···O and O–H···N hydrogen bonds link adjacent molecules into a linear chain structure.

The third acid and the carboxylate anion are disordered with respect to each other.

Related literature top

For the crystal structure of quinoline-2-carboxylic acid, see: Dobrzyńska & Jerzykiewicz (2004).

Experimental top

Quinoline-2-carboxylic acid (1 mmol, 0.17 g) and methyl-8-hydroxy quinoline (1 mmol, 0.16 g) were dissolved completely in warm acetonitrile; the solution was filtered into a clean beaker for the growth of colorless crystals.

As no potasium salt was used in the attempted co-crystallization of the organic compounds, the potassium in the crystal structure is better attributed to the presence of potassium quinoline-2-carboxylate present in the commercially procured carboxylic acid reagent.

Structure description top

The third acid and the carboxylate anion are disordered with respect to each other.

For the crystal structure of quinoline-2-carboxylic acid, see: Dobrzyńska & Jerzykiewicz (2004).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the polymeric chain structure of K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: i = x, 1 – y, 1/2 – z.

(Quinoline-2-carboxylato-κO)(quinoline-2-carboxylic acid-κO)bis(quinoline-2-carboxylic acid-κ²N,O)potassium top

Crystal data top

[K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃]	F(000) = 3024
M_r = 730.76	D_x = 1.442 Mg m⁻³
Orthorhombic, Ibca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2b 2c	Cell parameters from 8761 reflections
a = 17.8679 (10) Å	θ = 2.2–27.4°
b = 18.3617 (10) Å	µ = 0.22 mm⁻¹
c = 20.5162 (11) Å	T = 100 K
V = 6731.1 (6) Å³	Prism, colorless
Z = 8	0.24 × 0.08 × 0.04 mm

Data collection top

Bruker SMART APEX diffractometer	3888 independent reflections
Radiation source: fine-focus sealed tube	3025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.949, T_max = 0.991	k = −23→23
40797 measured reflections	l = −26→26

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0526P)² + 5.6795P] where P = (F_o² + 2F_c²)/3
3888 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃]	V = 6731.1 (6) Å³
M_r = 730.76	Z = 8
Orthorhombic, Ibca	Mo Kα radiation
a = 17.8679 (10) Å	µ = 0.22 mm⁻¹
b = 18.3617 (10) Å	T = 100 K
c = 20.5162 (11) Å	0.24 × 0.08 × 0.04 mm

Data collection top

Bruker SMART APEX diffractometer	3888 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3025 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.991	R_int = 0.075
40797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.32 e Å⁻³
3888 reflections	Δρ_min = −0.54 e Å⁻³
248 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
K1	0.21891 (3)	0.5000	0.2500	0.02083 (13)
O1	0.11657 (7)	0.56758 (6)	0.17738 (6)	0.0256 (3)
O2	0.03124 (6)	0.65608 (6)	0.16390 (6)	0.0232 (3)
O3	0.43403 (7)	0.52894 (7)	0.30384 (5)	0.0257 (3)
O4	0.32794 (6)	0.47403 (6)	0.33533 (5)	0.0245 (3)
N1	0.17250 (7)	0.64593 (7)	0.28227 (6)	0.0183 (3)
N2	0.45505 (7)	0.58087 (7)	0.42560 (6)	0.0171 (3)
C1	0.09152 (8)	0.62730 (9)	0.19030 (7)	0.0190 (3)
C2	0.12794 (8)	0.67785 (9)	0.23938 (7)	0.0175 (3)
C3	0.11455 (9)	0.75361 (9)	0.23657 (7)	0.0193 (3)
H3A	0.0804	0.7733	0.2057	0.023*
C4	0.15184 (8)	0.79806 (9)	0.27927 (7)	0.0195 (3)
H4	0.1460	0.8494	0.2769	0.023*
C5	0.19914 (8)	0.76670 (8)	0.32701 (7)	0.0179 (3)
C6	0.23871 (9)	0.80868 (9)	0.37409 (8)	0.0210 (3)
H6	0.2348	0.8603	0.3738	0.025*
C7	0.28244 (9)	0.77496 (9)	0.41982 (8)	0.0236 (4)
H7	0.3086	0.8034	0.4511	0.028*
C8	0.28908 (9)	0.69785 (9)	0.42095 (8)	0.0236 (4)
H8	0.3192	0.6751	0.4532	0.028*
C9	0.25237 (9)	0.65638 (9)	0.37590 (7)	0.0216 (3)
H9	0.2572	0.6049	0.3769	0.026*
C10	0.20707 (8)	0.68960 (8)	0.32758 (7)	0.0173 (3)
C11	0.38543 (9)	0.50923 (8)	0.34589 (7)	0.0184 (3)
C12	0.40191 (8)	0.53220 (8)	0.41573 (7)	0.0164 (3)
C13	0.36025 (9)	0.49993 (9)	0.46699 (8)	0.0203 (3)
H13	0.3214	0.4662	0.4577	0.024*
C14	0.37688 (9)	0.51806 (9)	0.53016 (8)	0.0218 (3)
H14	0.3505	0.4960	0.5652	0.026*
C15	0.43344 (9)	0.56978 (9)	0.54274 (7)	0.0192 (3)
C16	0.45424 (10)	0.59128 (9)	0.60692 (8)	0.0238 (4)
H16	0.4301	0.5700	0.6435	0.029*
C17	0.50871 (10)	0.64237 (10)	0.61602 (8)	0.0272 (4)
H17	0.5220	0.6566	0.6590	0.033*
C18	0.54557 (10)	0.67443 (10)	0.56217 (8)	0.0264 (4)
H18	0.5833	0.7100	0.5693	0.032*
C19	0.52729 (9)	0.65450 (9)	0.49966 (8)	0.0225 (3)
H19	0.5523	0.6763	0.4638	0.027*
C20	0.47121 (8)	0.60139 (8)	0.48864 (7)	0.0175 (3)
H2	0.0082 (13)	0.6266 (11)	0.1393 (10)	0.057 (8)*
H3	0.433 (2)	0.512 (3)	0.2662 (12)	0.051 (14)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0202 (2)	0.0198 (2)	0.0225 (2)	0.000	0.000	−0.00261 (19)
O1	0.0249 (6)	0.0250 (6)	0.0270 (6)	0.0012 (5)	−0.0050 (5)	−0.0085 (5)
O2	0.0218 (6)	0.0250 (6)	0.0227 (6)	−0.0007 (5)	−0.0062 (5)	−0.0032 (5)
O3	0.0272 (6)	0.0359 (7)	0.0140 (6)	−0.0066 (5)	0.0024 (5)	−0.0049 (5)
O4	0.0262 (6)	0.0257 (6)	0.0217 (6)	−0.0064 (5)	−0.0023 (5)	−0.0033 (5)
N1	0.0183 (6)	0.0201 (7)	0.0163 (6)	−0.0014 (5)	0.0018 (5)	−0.0021 (5)
N2	0.0176 (6)	0.0182 (7)	0.0154 (6)	0.0019 (5)	0.0001 (5)	−0.0012 (5)
C1	0.0183 (7)	0.0215 (8)	0.0171 (7)	−0.0022 (6)	0.0020 (6)	−0.0008 (6)
C2	0.0150 (7)	0.0214 (8)	0.0161 (7)	−0.0016 (6)	0.0026 (6)	−0.0026 (6)
C3	0.0175 (7)	0.0225 (8)	0.0180 (7)	0.0013 (6)	0.0008 (6)	0.0002 (6)
C4	0.0180 (7)	0.0195 (8)	0.0210 (7)	0.0012 (6)	0.0044 (6)	−0.0027 (6)
C5	0.0148 (7)	0.0207 (8)	0.0182 (7)	0.0000 (6)	0.0038 (6)	−0.0034 (6)
C6	0.0205 (8)	0.0215 (8)	0.0211 (7)	−0.0017 (6)	0.0036 (6)	−0.0051 (6)
C7	0.0212 (8)	0.0304 (9)	0.0191 (7)	−0.0024 (7)	0.0008 (6)	−0.0070 (7)
C8	0.0224 (8)	0.0305 (9)	0.0178 (7)	0.0036 (7)	−0.0023 (6)	−0.0014 (6)
C9	0.0224 (8)	0.0225 (8)	0.0198 (7)	0.0031 (6)	0.0012 (6)	−0.0018 (6)
C10	0.0168 (7)	0.0198 (8)	0.0154 (7)	−0.0005 (6)	0.0037 (5)	−0.0029 (6)
C11	0.0214 (8)	0.0169 (8)	0.0169 (7)	0.0021 (6)	−0.0018 (6)	−0.0009 (6)
C12	0.0160 (7)	0.0171 (7)	0.0162 (7)	0.0031 (6)	−0.0001 (5)	−0.0011 (6)
C13	0.0213 (8)	0.0196 (8)	0.0201 (7)	−0.0021 (6)	−0.0004 (6)	0.0008 (6)
C14	0.0245 (8)	0.0241 (9)	0.0168 (7)	0.0008 (7)	0.0020 (6)	0.0022 (6)
C15	0.0214 (8)	0.0198 (8)	0.0164 (7)	0.0056 (6)	−0.0011 (6)	−0.0020 (6)
C16	0.0285 (9)	0.0275 (9)	0.0155 (7)	0.0066 (7)	−0.0007 (6)	−0.0024 (6)
C17	0.0301 (9)	0.0299 (9)	0.0216 (8)	0.0075 (7)	−0.0070 (7)	−0.0094 (7)
C18	0.0231 (8)	0.0255 (9)	0.0306 (9)	0.0022 (7)	−0.0066 (7)	−0.0077 (7)
C19	0.0210 (8)	0.0226 (8)	0.0239 (8)	0.0006 (7)	−0.0009 (6)	−0.0027 (6)
C20	0.0176 (7)	0.0180 (8)	0.0170 (7)	0.0050 (6)	−0.0010 (6)	−0.0018 (6)

Geometric parameters (Å, º) top

K1—O4	2.6622 (12)	C6—C7	1.369 (2)
K1—O4ⁱ	2.6622 (12)	C6—H6	0.9500
K1—O1ⁱ	2.6653 (12)	C7—C8	1.421 (2)
K1—O1	2.6653 (12)	C7—H7	0.9500
K1—N1ⁱ	2.8820 (13)	C8—C9	1.365 (2)
K1—N1	2.8820 (13)	C8—H8	0.9500
O1—C1	1.2137 (19)	C9—C10	1.418 (2)
O2—C1	1.3163 (19)	C9—H9	0.9500
O2—H2	0.846 (10)	C11—C12	1.522 (2)
O3—C11	1.2765 (19)	C12—C13	1.418 (2)
O3—H3	0.836 (10)	C13—C14	1.371 (2)
O4—C11	1.2327 (19)	C13—H13	0.9500
N1—C2	1.323 (2)	C14—C15	1.411 (2)
N1—C10	1.3742 (19)	C14—H14	0.9500
N2—C12	1.320 (2)	C15—C20	1.423 (2)
N2—C20	1.3777 (19)	C15—C16	1.424 (2)
C1—C2	1.516 (2)	C16—C17	1.365 (2)
C2—C3	1.413 (2)	C16—H16	0.9500
C3—C4	1.370 (2)	C17—C18	1.414 (3)
C3—H3A	0.9500	C17—H17	0.9500
C4—C5	1.416 (2)	C18—C19	1.373 (2)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.424 (2)	C19—C20	1.416 (2)
C5—C10	1.423 (2)	C19—H19	0.9500

O4—K1—O4ⁱ	85.93 (5)	C6—C7—H7	119.7
O4—K1—O1ⁱ	92.93 (4)	C8—C7—H7	119.7
O4ⁱ—K1—O1ⁱ	162.38 (3)	C9—C8—C7	120.31 (15)
O4—K1—O1	162.38 (4)	C9—C8—H8	119.8
O4ⁱ—K1—O1	92.93 (4)	C7—C8—H8	119.8
O1ⁱ—K1—O1	93.36 (5)	C8—C9—C10	120.50 (15)
O4—K1—N1ⁱ	101.25 (4)	C8—C9—H9	119.7
O4ⁱ—K1—N1ⁱ	103.07 (4)	C10—C9—H9	119.7
O1ⁱ—K1—N1ⁱ	59.88 (4)	N1—C10—C9	118.60 (14)
O1—K1—N1ⁱ	96.14 (4)	N1—C10—C5	122.02 (14)
O4—K1—N1	103.07 (4)	C9—C10—C5	119.38 (14)
O4ⁱ—K1—N1	101.25 (4)	O4—C11—O3	126.64 (14)
O1ⁱ—K1—N1	96.14 (4)	O4—C11—C12	118.16 (14)
O1—K1—N1	59.88 (4)	O3—C11—C12	115.20 (13)
N1ⁱ—K1—N1	146.55 (5)	N2—C12—C13	123.15 (14)
C1—O1—K1	123.47 (10)	N2—C12—C11	118.12 (13)
C1—O2—H2	112.7 (17)	C13—C12—C11	118.73 (13)
C11—O3—H3	120 (3)	C14—C13—C12	119.07 (15)
C11—O4—K1	129.15 (10)	C14—C13—H13	120.5
C2—N1—C10	117.50 (13)	C12—C13—H13	120.5
C2—N1—K1	115.60 (10)	C13—C14—C15	119.46 (15)
C10—N1—K1	124.64 (10)	C13—C14—H14	120.3
C12—N2—C20	118.69 (13)	C15—C14—H14	120.3
O1—C1—O2	125.07 (14)	C14—C15—C20	118.15 (14)
O1—C1—C2	122.68 (14)	C14—C15—C16	122.87 (15)
O2—C1—C2	112.25 (13)	C20—C15—C16	118.97 (15)
N1—C2—C3	124.42 (14)	C17—C16—C15	120.21 (16)
N1—C2—C1	115.38 (14)	C17—C16—H16	119.9
C3—C2—C1	120.19 (13)	C15—C16—H16	119.9
C4—C3—C2	118.55 (14)	C16—C17—C18	120.75 (15)
C4—C3—H3A	120.7	C16—C17—H17	119.6
C2—C3—H3A	120.7	C18—C17—H17	119.6
C3—C4—C5	119.35 (15)	C19—C18—C17	120.52 (16)
C3—C4—H4	120.3	C19—C18—H18	119.7
C5—C4—H4	120.3	C17—C18—H18	119.7
C4—C5—C6	123.06 (15)	C18—C19—C20	120.06 (16)
C4—C5—C10	118.02 (14)	C18—C19—H19	120.0
C6—C5—C10	118.92 (14)	C20—C19—H19	120.0
C7—C6—C5	120.24 (15)	N2—C20—C19	119.10 (14)
C7—C6—H6	119.9	N2—C20—C15	121.42 (14)
C5—C6—H6	119.9	C19—C20—C15	119.47 (14)
C6—C7—C8	120.63 (15)

O4—K1—O1—C1	−19.8 (2)	C6—C7—C8—C9	0.6 (2)
O4ⁱ—K1—O1—C1	−105.57 (12)	C7—C8—C9—C10	−0.2 (2)
O1ⁱ—K1—O1—C1	90.90 (12)	C2—N1—C10—C9	177.15 (13)
N1ⁱ—K1—O1—C1	150.95 (12)	K1—N1—C10—C9	−20.70 (18)
N1—K1—O1—C1	−4.26 (11)	C2—N1—C10—C5	−3.3 (2)
O4ⁱ—K1—O4—C11	45.39 (12)	K1—N1—C10—C5	158.83 (10)
O1ⁱ—K1—O4—C11	−152.23 (13)	C8—C9—C10—N1	178.53 (14)
O1—K1—O4—C11	−41.5 (2)	C8—C9—C10—C5	−1.0 (2)
N1ⁱ—K1—O4—C11	147.92 (13)	C4—C5—C10—N1	2.2 (2)
N1—K1—O4—C11	−55.23 (13)	C6—C5—C10—N1	−177.82 (13)
O4—K1—N1—C2	167.93 (10)	C4—C5—C10—C9	−178.25 (14)
O4ⁱ—K1—N1—C2	79.54 (11)	C6—C5—C10—C9	1.7 (2)
O1ⁱ—K1—N1—C2	−97.62 (10)	K1—O4—C11—O3	−53.0 (2)
O1—K1—N1—C2	−7.30 (10)	K1—O4—C11—C12	127.14 (12)
N1ⁱ—K1—N1—C2	−56.46 (10)	C20—N2—C12—C13	0.2 (2)
O4—K1—N1—C10	5.47 (12)	C20—N2—C12—C11	−179.12 (13)
O4ⁱ—K1—N1—C10	−82.91 (11)	O4—C11—C12—N2	−167.51 (14)
O1ⁱ—K1—N1—C10	99.93 (11)	O3—C11—C12—N2	12.7 (2)
O1—K1—N1—C10	−169.75 (13)	O4—C11—C12—C13	13.2 (2)
N1ⁱ—K1—N1—C10	141.09 (12)	O3—C11—C12—C13	−166.67 (14)
K1—O1—C1—O2	−165.66 (11)	N2—C12—C13—C14	−2.0 (2)
K1—O1—C1—C2	14.9 (2)	C11—C12—C13—C14	177.30 (14)
C10—N1—C2—C3	1.0 (2)	C12—C13—C14—C15	1.8 (2)
K1—N1—C2—C3	−162.79 (11)	C13—C14—C15—C20	0.1 (2)
C10—N1—C2—C1	179.71 (12)	C13—C14—C15—C16	−179.71 (15)
K1—N1—C2—C1	15.95 (16)	C14—C15—C16—C17	−179.08 (15)
O1—C1—C2—N1	−21.4 (2)	C20—C15—C16—C17	1.1 (2)
O2—C1—C2—N1	159.12 (13)	C15—C16—C17—C18	−0.3 (2)
O1—C1—C2—C3	157.39 (15)	C16—C17—C18—C19	−0.2 (3)
O2—C1—C2—C3	−22.09 (19)	C17—C18—C19—C20	−0.1 (2)
N1—C2—C3—C4	2.5 (2)	C12—N2—C20—C19	−178.94 (14)
C1—C2—C3—C4	−176.21 (14)	C12—N2—C20—C15	1.8 (2)
C2—C3—C4—C5	−3.5 (2)	C18—C19—C20—N2	−178.40 (14)
C3—C4—C5—C6	−178.65 (14)	C18—C19—C20—C15	0.9 (2)
C3—C4—C5—C10	1.3 (2)	C14—C15—C20—N2	−1.9 (2)
C4—C5—C6—C7	178.70 (15)	C16—C15—C20—N2	177.87 (14)
C10—C5—C6—C7	−1.3 (2)	C14—C15—C20—C19	178.81 (14)
C5—C6—C7—C8	0.1 (2)	C16—C15—C20—C19	−1.4 (2)

Symmetry code: (i) x, −y+1, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2ⁱⁱ	0.85 (1)	1.84 (1)	2.671 (2)	167 (2)
O3—H3···O3ⁱ	0.84 (1)	1.62 (1)	2.452 (2)	175 (6)

Symmetry codes: (i) x, −y+1, −z+1/2; (ii) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[K(C₁₀H₆NO₂)(C₁₀H₇NO₂)₃]
M_r	730.76
Crystal system, space group	Orthorhombic, Ibca
Temperature (K)	100
a, b, c (Å)	17.8679 (10), 18.3617 (10), 20.5162 (11)
V (Å³)	6731.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.08 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	40797, 3888, 3025
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 1.01
No. of reflections	3888
No. of parameters	248
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2ⁱ	0.85 (1)	1.84 (1)	2.671 (2)	167 (2)
O3—H3···O3ⁱⁱ	0.84 (1)	1.62 (1)	2.452 (2)	175 (6)

Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x, −y+1, −z+1/2.

Acknowledgements

I thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dobrzyńska, D. & Jerzykiewicz, L. B. (2004). J. Chem. Crystallogr. 34, 51–55. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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