



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810027510/jh2182sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810027510/jh2182Isup2.hkl |
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.102
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 5.68 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
Hydrogen atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
Of the two carboxylic acid hydrogen atoms, that connected to O2 lies on a general position and has full site-occupancy. That connected to O3 is near the Wyckoff 8c site so that the atom should have only half site-occupancy. The refinement of the two hydrogen atoms with a distance restraint of O–H 0.84±0.01 Å gave satisfactory temperature factors.
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.
For the crystal structure of quinoline-2-carboxylic acid, see: Dobrzyńska & Jerzykiewicz (2004).
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).
[K(C10H6NO2)(C10H7NO2)3] | F(000) = 3024 |
Mr = 730.76 | Dx = 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 |
Bruker SMART APEX diffractometer | 3888 independent reflections |
Radiation source: fine-focus sealed tube | 3025 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
Tmin = 0.949, Tmax = 0.991 | k = −23→23 |
40797 measured reflections | l = −26→26 |
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(Fo2) + (0.0526P)2 + 5.6795P] where P = (Fo2 + 2Fc2)/3 |
3888 reflections | (Δ/σ)max = 0.001 |
248 parameters | Δρmax = 0.32 e Å−3 |
2 restraints | Δρmin = −0.54 e Å−3 |
[K(C10H6NO2)(C10H7NO2)3] | V = 6731.1 (6) Å3 |
Mr = 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 |
Bruker SMART APEX diffractometer | 3888 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3025 reflections with I > 2σ(I) |
Tmin = 0.949, Tmax = 0.991 | Rint = 0.075 |
40797 measured reflections |
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 | Δρmax = 0.32 e Å−3 |
3888 reflections | Δρmin = −0.54 e Å−3 |
248 parameters |
x | y | z | Uiso*/Ueq | 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 |
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) |
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. |
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] |
Mr | 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) |
Tmin, Tmax | 0.949, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40797, 3888, 3025 |
Rint | 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 |
Δρmax, Δρmin (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).
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. |
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.