Poly[(μ3-rac-5-eth­oxy­carbonyl-6-hy­droxy-6-methyl-4-phenyl-4,5,6,7-tetra­hydro­benzo[c]isoxazol-3-olato)potassium]

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.

doi:10.1107/S160053681101868X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m786

doi:10.1107/S160053681101868X

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Poly[(μ₃-rac-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-phenyl-4,5,6,7-tetrahydrobenzo[c]isoxazol-3-olato)potassium]

Abel M. Maharramov,^a ^* Arif I. Ismiyev ^a and Bahruz A. Rashidov ^a

^aBaku State University, Z. Khalilov St. 23, Baku AZ-1148, Azerbaijan
^*Correspondence e-mail: orglab@mail.ru

(Received 21 March 2011; accepted 17 May 2011; online 25 May 2011)

The title compound, [K(C₁₇H₁₈NO₅)]_n, reveals the relative configuration (4R*,5S*,6R*) whereas its crystals are racemic. The cyclohexane ring adopts a half-chair conformation and the isoxazole ring has an envelope conformation. The ethyl fragment of the ethoxycarbonyl group at position 5 is disordered in a 0.547 (7):0.453 (7) ratio. The K⁺ ion is surrounded by five O atoms from three ligands at distances ranging from 2.606 (2) to 3.028 (2) Å, generating a three-dimensional network. The crystal packing displays intermolecular O—H⋯N and O—H⋯O hydrogen bonds in which the hydroxy group acts as a double proton donor.

Related literature

For background to the microbiological activity of 2-azetidinone derivatives, see: Wadher et al. (2009 ).

Experimental

Crystal data

[K(C₁₇H₁₈NO₅)]
M_r = 355.42
Monoclinic, P 2₁ /c
a = 12.4811 (18) Å
b = 15.411 (2) Å
c = 8.6647 (12) Å
β = 94.388 (5)°
V = 1661.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.903, T_max = 0.934
16716 measured reflections
3594 independent reflections
2977 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.149
S = 0.99
3594 reflections
221 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6O⋯N1ⁱ	0.91	1.88	2.784 (3)	177
O6—H6O⋯O2ⁱ	0.91	2.55	3.336 (3)	145
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101868X/kp2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101868X/kp2318Isup2.hkl

checkCIF report

Comment top

Schiff-base compounds have been used as fine chemicals and medical substrates. They are associated with antibacterial, antifungal and antitubercular activities and have diverse biological activities. Literature revealed that 2-azetidinone derivatives occupy an important place in medicinal chemistry as they show a variety of microbiological activity (Wadher et al.2009).

The molecules (I) are diastereomers and possess three asymmetric centers at C4, C5 and C6 carbon atoms. The crystal of (I) is racemate and consists of enantiomeric pairs with the relative configuration of the centres of rac-4R*,5S*,6R*. The cyclohexane ring adopts a half-chair conformation (Fig. 1). Izoxazole ring has an envelope conformation. The fragment of a ring C7a—N1—O2—C3 is almost planar - torsion angle is 1.0 (2) °. The phenyl ring is in a pseudo-equatorial position. Torsion angle between the ethoxycarbonyl group and the phenyl substituent is C8—C4—C5—C14 is -61.3 (2)° which indicates a pseudo-axial location of hydrogen atoms at C4 and C5. K+ creates coordination with the contacts: from the same ligand K1···O4–2.688 (2) and K1···O6–2.804 (2)Å; from one ligand K1···O3–2.606 (2)%A [-x,1-y, 1-z] and with an additional ligand K1···O3 2.701 (2) and K1···O2 3.028 (2)Å [x,y,-1+z]. O3 atoms form double bridges between the two K+ (Fig. 2) The closest contac K1—C12 is 3.372 (2) Å. The crystal structure involves O—H···N and O—H···O hydrogen bonds (Table 1 and Fig. 3).

Related literature top

For background to the microbiological activity of 2-azetidinone derivatives, see: Wadher et al. (2009).

Experimental top

(rac)-Diethyl-4-hydroxy-4-methyl-6-oxo-2-phenyl-1,3-dicarboxylate (20 mmol), hydroxylamine hydrochloride (20 mmol) were dissolved in 20 mL ethanol. The mixture was stirred at 345–350 K for 10 min. Then added 40 (mmol) potassium bicarbonate and continued with mixing up to 10 h. After cooling to a room temperature white crystals were obtained. The crystals were filtered and washed with ethanol. Then they were dissolved in ethanol (50 mL) and recrystallised to yield colourless block-shaped crystals for structure determination.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The polymeric structure of the title compound.
	Fig. 3. The hydrogen-bonded (dashed lines) packing in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

Poly[(µ₃-rac-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-phenyl-4,5,6,7- tetrahydrobenzo[c]isoxazol-3-olato)potassium] top

Crystal data top

[K(C₁₇H₁₈NO₅)]	F(000) = 744
M_r = 355.42	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2419 reflections
a = 12.4811 (18) Å	θ = 2.7–32.7°
b = 15.411 (2) Å	µ = 0.35 mm⁻¹
c = 8.6647 (12) Å	T = 100 K
β = 94.388 (5)°	Prism, colorless
V = 1661.7 (4) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3594 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→15
T_min = 0.903, T_max = 0.934	k = −19→19
16716 measured reflections	l = −11→11

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)] = 0.054	Hydrogen site location: difference Fourier map
wR(F²) = 0.149	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.080P)² + 1.240P] where P = (F_o² + 2F_c²)/3
3594 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.68 e Å⁻³
6 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[K(C₁₇H₁₈NO₅)]	V = 1661.7 (4) Å³
M_r = 355.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4811 (18) Å	µ = 0.35 mm⁻¹
b = 15.411 (2) Å	T = 100 K
c = 8.6647 (12) Å	0.30 × 0.30 × 0.20 mm
β = 94.388 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3594 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2977 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.934	R_int = 0.042
16716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	6 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 0.99	Δρ_max = 0.68 e Å⁻³
3594 reflections	Δρ_min = −0.64 e Å⁻³
221 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
K1	0.05763 (5)	0.40629 (3)	0.14073 (6)	0.04742 (19)
N1	0.28041 (17)	0.31949 (12)	0.8020 (2)	0.0439 (5)
O2	0.19438 (14)	0.35565 (10)	0.88107 (18)	0.0439 (4)
C3	0.15026 (18)	0.42478 (13)	0.7957 (2)	0.0343 (4)
O3	0.07151 (14)	0.46143 (11)	0.84704 (18)	0.0440 (4)
C3A	0.20830 (16)	0.43430 (12)	0.6674 (2)	0.0308 (4)
C4	0.19038 (16)	0.49360 (12)	0.5307 (2)	0.0276 (4)
H4	0.1313	0.4679	0.4608	0.033*
C5	0.29248 (17)	0.49356 (13)	0.4414 (2)	0.0323 (4)
H5	0.3515	0.5229	0.5063	0.039*
O4	0.19551 (16)	0.53784 (12)	0.2040 (2)	0.0537 (5)
O5	0.35688 (16)	0.59290 (14)	0.2631 (3)	0.0684 (6)
C6	0.32838 (17)	0.39892 (13)	0.4075 (3)	0.0344 (4)
O6	0.23646 (12)	0.35629 (9)	0.33610 (18)	0.0389 (4)
H6O	0.2512	0.2992	0.3219	0.058*
C7	0.36413 (18)	0.35424 (14)	0.5608 (3)	0.0399 (5)
H7A	0.3724	0.2912	0.5430	0.048*
H7B	0.4348	0.3775	0.6007	0.048*
C7A	0.28494 (17)	0.36821 (13)	0.6776 (2)	0.0343 (4)
C8	0.15431 (16)	0.58394 (12)	0.5748 (2)	0.0296 (4)
C9	0.2076 (2)	0.63132 (15)	0.6927 (3)	0.0455 (6)
H9	0.2712	0.6087	0.7452	0.055*
C10	0.1689 (3)	0.71179 (16)	0.7348 (3)	0.0551 (7)
H10	0.2067	0.7440	0.8152	0.066*
C11	0.0769 (2)	0.74512 (15)	0.6616 (3)	0.0499 (6)
H11	0.0510	0.8003	0.6907	0.060*
C12	0.0223 (2)	0.69854 (14)	0.5464 (3)	0.0432 (5)
H12	−0.0425	0.7207	0.4968	0.052*
C13	0.06184 (17)	0.61842 (13)	0.5017 (2)	0.0334 (4)
H13	0.0245	0.5872	0.4198	0.040*
C14	0.2736 (2)	0.54270 (14)	0.2906 (3)	0.0399 (5)
C15	0.3426 (6)	0.6209 (6)	0.1016 (5)	0.0951 (18)	0.547 (7)
H15A	0.2725	0.6506	0.0820	0.114*	0.547 (7)
H15B	0.3437	0.5700	0.0320	0.114*	0.547 (7)
C16	0.4336 (5)	0.6826 (5)	0.0708 (8)	0.0951 (18)	0.547 (7)
H16A	0.4368	0.6899	−0.0411	0.143*	0.547 (7)
H16B	0.5018	0.6586	0.1154	0.143*	0.547 (7)
H16C	0.4208	0.7390	0.1183	0.143*	0.547 (7)
C15'	0.3639 (8)	0.6479 (5)	0.1291 (8)	0.0951 (18)	0.45
H15C	0.3928	0.7055	0.1613	0.114*	0.453 (7)
H15D	0.2916	0.6563	0.0758	0.114*	0.453 (7)
C16'	0.4377 (7)	0.6047 (6)	0.0203 (7)	0.0951 (18)	0.45
H16D	0.4374	0.6381	−0.0760	0.143*	0.453 (7)
H16E	0.4124	0.5456	−0.0029	0.143*	0.453 (7)
H16F	0.5110	0.6025	0.0698	0.143*	0.453 (7)
C17	0.4187 (2)	0.39617 (19)	0.2990 (3)	0.0540 (6)
H17A	0.4443	0.3364	0.2905	0.081*
H17B	0.4780	0.4332	0.3402	0.081*
H17C	0.3919	0.4172	0.1965	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0625 (4)	0.0453 (3)	0.0344 (3)	0.0047 (2)	0.0035 (2)	0.0039 (2)
N1	0.0531 (12)	0.0367 (9)	0.0414 (11)	0.0073 (8)	0.0011 (9)	0.0112 (8)
O2	0.0589 (10)	0.0395 (8)	0.0335 (8)	0.0062 (7)	0.0046 (7)	0.0133 (6)
C3	0.0453 (12)	0.0308 (9)	0.0259 (9)	−0.0015 (8)	−0.0034 (8)	0.0037 (7)
O3	0.0528 (10)	0.0494 (9)	0.0308 (8)	0.0095 (7)	0.0106 (7)	0.0049 (7)
C3A	0.0375 (10)	0.0257 (9)	0.0285 (9)	0.0010 (7)	−0.0010 (8)	0.0029 (7)
C4	0.0349 (10)	0.0243 (8)	0.0233 (8)	−0.0009 (7)	−0.0003 (7)	0.0012 (7)
C5	0.0368 (10)	0.0295 (9)	0.0307 (10)	−0.0032 (8)	0.0019 (8)	0.0003 (7)
O4	0.0706 (12)	0.0517 (10)	0.0373 (9)	−0.0031 (9)	−0.0058 (8)	0.0109 (7)
O5	0.0561 (12)	0.0650 (12)	0.0866 (16)	−0.0045 (9)	0.0216 (11)	0.0378 (11)
C6	0.0355 (11)	0.0332 (10)	0.0348 (11)	0.0016 (8)	0.0040 (8)	−0.0018 (8)
O6	0.0453 (9)	0.0297 (7)	0.0405 (8)	0.0019 (6)	−0.0035 (7)	−0.0067 (6)
C7	0.0389 (12)	0.0365 (11)	0.0437 (12)	0.0074 (9)	0.0003 (9)	0.0036 (9)
C7A	0.0398 (11)	0.0280 (9)	0.0341 (10)	0.0006 (8)	−0.0045 (8)	0.0030 (8)
C8	0.0397 (11)	0.0247 (9)	0.0242 (9)	−0.0012 (7)	0.0020 (8)	0.0009 (7)
C9	0.0575 (14)	0.0371 (11)	0.0397 (12)	0.0037 (10)	−0.0121 (10)	−0.0069 (9)
C10	0.0815 (19)	0.0385 (12)	0.0438 (13)	−0.0020 (12)	−0.0045 (13)	−0.0142 (10)
C11	0.0770 (18)	0.0297 (10)	0.0443 (13)	0.0099 (11)	0.0132 (12)	−0.0003 (9)
C12	0.0544 (14)	0.0341 (11)	0.0418 (12)	0.0109 (9)	0.0086 (10)	0.0105 (9)
C13	0.0419 (11)	0.0301 (9)	0.0284 (10)	0.0015 (8)	0.0033 (8)	0.0058 (8)
C14	0.0526 (13)	0.0326 (10)	0.0365 (11)	0.0013 (9)	0.0160 (10)	0.0047 (8)
C15	0.074 (2)	0.115 (4)	0.100 (3)	−0.008 (2)	0.026 (2)	0.065 (3)
C16	0.074 (2)	0.115 (4)	0.100 (3)	−0.008 (2)	0.026 (2)	0.065 (3)
C15'	0.074 (2)	0.115 (4)	0.100 (3)	−0.008 (2)	0.026 (2)	0.065 (3)
C16'	0.074 (2)	0.115 (4)	0.100 (3)	−0.008 (2)	0.026 (2)	0.065 (3)
C17	0.0547 (15)	0.0561 (15)	0.0537 (16)	0.0096 (12)	0.0215 (12)	0.0014 (12)

Geometric parameters (Å, º) top

K1—O3ⁱ	2.6059 (17)	O6—H6O	0.9092
K1—O4	2.688 (2)	C7—C7A	1.483 (3)
K1—O3ⁱⁱ	2.7010 (16)	C7—H7A	0.9900
K1—O6	2.8042 (16)	C7—H7B	0.9900
K1—O2ⁱⁱ	3.0285 (18)	C8—C13	1.380 (3)
K1—C3ⁱⁱ	3.299 (2)	C8—C9	1.384 (3)
K1—C12ⁱ	3.372 (2)	C9—C10	1.390 (3)
K1—C11ⁱ	3.411 (3)	C9—H9	0.9500
K1—K1ⁱⁱⁱ	3.9778 (11)	C10—C11	1.369 (4)
N1—C7A	1.318 (3)	C10—H10	0.9500
N1—O2	1.430 (3)	C11—C12	1.368 (4)
O2—C3	1.387 (2)	C11—K1ⁱ	3.411 (3)
O2—K1^iv	3.0285 (18)	C11—H11	0.9500
C3—O3	1.245 (3)	C12—C13	1.395 (3)
C3—C3A	1.380 (3)	C12—K1ⁱ	3.372 (2)
C3—K1^iv	3.299 (2)	C12—H12	0.9500
O3—K1ⁱ	2.6059 (17)	C13—H13	0.9500
O3—K1^iv	2.7011 (16)	C15—C16	1.520 (3)
C3A—C7A	1.395 (3)	C15—H15A	0.9900
C3A—C4	1.499 (3)	C15—H15B	0.9900
C4—C8	1.521 (3)	C16—H16A	0.9800
C4—C5	1.541 (3)	C16—H16B	0.9800
C4—H4	1.0000	C16—H16C	0.9800
C5—C14	1.513 (3)	C15'—C16'	1.522 (3)
C5—C6	1.560 (3)	C15'—H15C	0.9900
C5—H5	1.0000	C15'—H15D	0.9900
O4—C14	1.187 (3)	C16'—H16D	0.9800
O5—C14	1.332 (3)	C16'—H16E	0.9800
O5—C15'	1.446 (3)	C16'—H16F	0.9800
O5—C15	1.462 (3)	C17—H17A	0.9800
C6—O6	1.422 (3)	C17—H17B	0.9800
C6—C17	1.523 (3)	C17—H17C	0.9800
C6—C7	1.532 (3)

O3ⁱ—K1—O4	77.88 (6)	O6—C6—C7	109.96 (17)
O3ⁱ—K1—O3ⁱⁱ	82.92 (5)	C17—C6—C7	110.03 (19)
O4—K1—O3ⁱⁱ	82.45 (6)	O6—C6—C5	106.27 (16)
O3ⁱ—K1—O6	131.05 (5)	C17—C6—C5	112.27 (18)
O4—K1—O6	67.46 (5)	C7—C6—C5	109.00 (17)
O3ⁱⁱ—K1—O6	123.35 (5)	C6—O6—K1	135.57 (12)
O3ⁱ—K1—O2ⁱⁱ	128.12 (5)	C6—O6—H6O	110.0
O4—K1—O2ⁱⁱ	87.56 (6)	K1—O6—H6O	110.1
O3ⁱⁱ—K1—O2ⁱⁱ	45.63 (5)	C7A—C7—C6	111.18 (17)
O6—K1—O2ⁱⁱ	84.83 (5)	C7A—C7—H7A	109.4
O3ⁱ—K1—C3ⁱⁱ	103.30 (5)	C6—C7—H7A	109.4
O4—K1—C3ⁱⁱ	81.74 (6)	C7A—C7—H7B	109.4
O3ⁱⁱ—K1—C3ⁱⁱ	21.07 (5)	C6—C7—H7B	109.4
O6—K1—C3ⁱⁱ	104.65 (5)	H7A—C7—H7B	108.0
O2ⁱⁱ—K1—C3ⁱⁱ	24.85 (5)	N1—C7A—C3A	113.3 (2)
O3ⁱ—K1—C12ⁱ	96.90 (5)	N1—C7A—C7	123.19 (19)
O4—K1—C12ⁱ	114.94 (6)	C3A—C7A—C7	123.52 (19)
O3ⁱⁱ—K1—C12ⁱ	162.27 (6)	C13—C8—C9	118.26 (19)
O6—K1—C12ⁱ	69.74 (6)	C13—C8—C4	119.40 (17)
O2ⁱⁱ—K1—C12ⁱ	133.79 (5)	C9—C8—C4	122.23 (18)
C3ⁱⁱ—K1—C12ⁱ	156.31 (6)	C8—C9—C10	120.5 (2)
O3ⁱ—K1—C11ⁱ	100.67 (6)	C8—C9—H9	119.7
O4—K1—C11ⁱ	138.20 (6)	C10—C9—H9	119.7
O3ⁱⁱ—K1—C11ⁱ	139.26 (6)	C11—C10—C9	120.6 (2)
O6—K1—C11ⁱ	84.75 (6)	C11—C10—H10	119.7
O2ⁱⁱ—K1—C11ⁱ	121.58 (5)	C9—C10—H10	119.7
C3ⁱⁱ—K1—C11ⁱ	137.22 (6)	C12—C11—C10	119.6 (2)
C12ⁱ—K1—C11ⁱ	23.26 (6)	C12—C11—K1ⁱ	76.75 (14)
O3ⁱ—K1—K1ⁱⁱⁱ	42.37 (3)	C10—C11—K1ⁱ	86.48 (16)
O4—K1—K1ⁱⁱⁱ	76.89 (4)	C12—C11—H11	120.2
O3ⁱⁱ—K1—K1ⁱⁱⁱ	40.55 (4)	C10—C11—H11	120.2
O6—K1—K1ⁱⁱⁱ	143.46 (4)	K1ⁱ—C11—H11	106.8
O2ⁱⁱ—K1—K1ⁱⁱⁱ	85.96 (3)	C11—C12—C13	120.0 (2)
C3ⁱⁱ—K1—K1ⁱⁱⁱ	61.12 (4)	C11—C12—K1ⁱ	79.98 (14)
C12ⁱ—K1—K1ⁱⁱⁱ	136.51 (5)	C13—C12—K1ⁱ	86.09 (12)
C11ⁱ—K1—K1ⁱⁱⁱ	129.48 (5)	C11—C12—H12	120.0
C7A—N1—O2	104.50 (17)	C13—C12—H12	120.0
C3—O2—N1	109.00 (16)	K1ⁱ—C12—H12	104.0
C3—O2—K1^iv	88.57 (12)	C8—C13—C12	121.0 (2)
N1—O2—K1^iv	160.52 (12)	C8—C13—H13	119.5
O3—C3—C3A	135.81 (19)	C12—C13—H13	119.5
O3—C3—O2	116.73 (19)	O4—C14—O5	122.5 (2)
C3A—C3—O2	107.45 (18)	O4—C14—C5	125.5 (2)
O3—C3—K1^iv	51.27 (11)	O5—C14—C5	112.0 (2)
C3A—C3—K1^iv	168.76 (15)	O5—C15—C16	108.3 (3)
O2—C3—K1^iv	66.58 (11)	O5—C15—H15A	110.0
C3—O3—K1ⁱ	151.29 (14)	C16—C15—H15A	110.0
C3—O3—K1^iv	107.66 (13)	O5—C15—H15B	110.0
K1ⁱ—O3—K1^iv	97.08 (5)	C16—C15—H15B	110.0
C3—C3A—C7A	105.72 (18)	H15A—C15—H15B	108.4
C3—C3A—C4	130.19 (18)	O5—C15'—C16'	108.5 (3)
C7A—C3A—C4	123.71 (18)	O5—C15'—H15C	110.0
C3A—C4—C8	112.89 (15)	C16'—C15'—H15C	110.0
C3A—C4—C5	108.52 (16)	O5—C15'—H15D	110.0
C8—C4—C5	113.49 (16)	C16'—C15'—H15D	110.0
C3A—C4—H4	107.2	H15C—C15'—H15D	108.4
C8—C4—H4	107.2	C15'—C16'—H16D	109.5
C5—C4—H4	107.2	C15'—C16'—H16E	109.5
C14—C5—C4	110.71 (17)	H16D—C16'—H16E	109.5
C14—C5—C6	109.48 (17)	C15'—C16'—H16F	109.5
C4—C5—C6	110.82 (16)	H16D—C16'—H16F	109.5
C14—C5—H5	108.6	H16E—C16'—H16F	109.5
C4—C5—H5	108.6	C6—C17—H17A	109.5
C6—C5—H5	108.6	C6—C17—H17B	109.5
C14—O4—K1	131.21 (15)	H17A—C17—H17B	109.5
C14—O5—C15'	125.5 (5)	C6—C17—H17C	109.5
C14—O5—C15	107.7 (3)	H17A—C17—H17C	109.5
C15'—O5—C15	21.4 (5)	H17B—C17—H17C	109.5
O6—C6—C17	109.24 (19)

C7A—N1—O2—C3	1.0 (2)	O2ⁱⁱ—K1—O6—C6	92.04 (18)
C7A—N1—O2—K1^iv	−152.5 (3)	C3ⁱⁱ—K1—O6—C6	76.92 (18)
N1—O2—C3—O3	177.58 (19)	C12ⁱ—K1—O6—C6	−127.24 (18)
K1^iv—O2—C3—O3	−10.98 (19)	C11ⁱ—K1—O6—C6	−145.53 (18)
N1—O2—C3—C3A	−1.6 (2)	K1ⁱⁱⁱ—K1—O6—C6	16.0 (2)
K1^iv—O2—C3—C3A	169.83 (15)	O6—C6—C7—C7A	−68.8 (2)
N1—O2—C3—K1^iv	−171.44 (16)	C17—C6—C7—C7A	170.8 (2)
C3A—C3—O3—K1ⁱ	−19.9 (5)	C5—C6—C7—C7A	47.3 (2)
O2—C3—O3—K1ⁱ	161.3 (2)	O2—N1—C7A—C3A	0.0 (3)
K1^iv—C3—O3—K1ⁱ	148.3 (4)	O2—N1—C7A—C7	179.66 (19)
C3A—C3—O3—K1^iv	−168.2 (2)	C3—C3A—C7A—N1	−0.9 (3)
O2—C3—O3—K1^iv	12.9 (2)	C4—C3A—C7A—N1	−174.48 (19)
O3—C3—C3A—C7A	−177.4 (3)	C3—C3A—C7A—C7	179.4 (2)
O2—C3—C3A—C7A	1.5 (2)	C4—C3A—C7A—C7	5.8 (3)
K1^iv—C3—C3A—C7A	57.8 (8)	C6—C7—C7A—N1	161.3 (2)
O3—C3—C3A—C4	−4.5 (4)	C6—C7—C7A—C3A	−19.0 (3)
O2—C3—C3A—C4	174.50 (19)	C3A—C4—C8—C13	−126.32 (19)
K1^iv—C3—C3A—C4	−129.3 (7)	C5—C4—C8—C13	109.7 (2)
C3—C3A—C4—C8	40.0 (3)	C3A—C4—C8—C9	49.8 (3)
C7A—C3A—C4—C8	−148.17 (19)	C5—C4—C8—C9	−74.2 (3)
C3—C3A—C4—C5	166.7 (2)	C13—C8—C9—C10	−0.5 (4)
C7A—C3A—C4—C5	−21.5 (3)	C4—C8—C9—C10	−176.6 (2)
C3A—C4—C5—C14	172.36 (16)	C8—C9—C10—C11	0.7 (4)
C8—C4—C5—C14	−61.3 (2)	C9—C10—C11—C12	0.3 (4)
C3A—C4—C5—C6	50.7 (2)	C9—C10—C11—K1ⁱ	72.9 (3)
C8—C4—C5—C6	177.04 (16)	C10—C11—C12—C13	−1.4 (4)
O3ⁱ—K1—O4—C14	137.7 (2)	K1ⁱ—C11—C12—C13	−79.5 (2)
O3ⁱⁱ—K1—O4—C14	−138.0 (2)	C10—C11—C12—K1ⁱ	78.1 (2)
O6—K1—O4—C14	−7.0 (2)	C9—C8—C13—C12	−0.7 (3)
O2ⁱⁱ—K1—O4—C14	−92.4 (2)	C4—C8—C13—C12	175.58 (18)
C3ⁱⁱ—K1—O4—C14	−116.7 (2)	C11—C12—C13—C8	1.7 (3)
C12ⁱ—K1—O4—C14	45.6 (2)	K1ⁱ—C12—C13—C8	−74.42 (19)
C11ⁱ—K1—O4—C14	45.2 (3)	K1—O4—C14—O5	148.93 (19)
K1ⁱⁱⁱ—K1—O4—C14	−178.8 (2)	K1—O4—C14—C5	−30.2 (3)
C14—C5—C6—O6	−70.3 (2)	C15'—O5—C14—O4	0.8 (5)
C4—C5—C6—O6	52.1 (2)	C15—O5—C14—O4	−12.5 (5)
C14—C5—C6—C17	49.0 (3)	C15'—O5—C14—C5	−180.0 (4)
C4—C5—C6—C17	171.44 (19)	C15—O5—C14—C5	166.8 (5)
C14—C5—C6—C7	171.22 (18)	C4—C5—C14—O4	−42.8 (3)
C4—C5—C6—C7	−66.4 (2)	C6—C5—C14—O4	79.6 (3)
C17—C6—O6—K1	−89.3 (2)	C4—C5—C14—O5	137.97 (19)
C7—C6—O6—K1	149.81 (14)	C6—C5—C14—O5	−99.6 (2)
C5—C6—O6—K1	32.0 (2)	C14—O5—C15—C16	176.7 (6)
O3ⁱ—K1—O6—C6	−45.9 (2)	C15'—O5—C15—C16	27.6 (11)
O4—K1—O6—C6	2.54 (17)	C14—O5—C15'—C16'	−104.3 (7)
O3ⁱⁱ—K1—O6—C6	66.21 (19)	C15—O5—C15'—C16'	−67.4 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6O···N1^v	0.91	1.88	2.784 (3)	177
O6—H6O···O2^v	0.91	2.55	3.336 (3)	145

Symmetry code: (v) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[K(C₁₇H₁₈NO₅)]
M_r	355.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.4811 (18), 15.411 (2), 8.6647 (12)
β (°)	94.388 (5)
V (Å³)	1661.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.903, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	16716, 3594, 2977
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.149, 0.99
No. of reflections	3594
No. of parameters	221
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.64

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6O···N1ⁱ	0.91	1.88	2.784 (3)	177
O6—H6O···O2ⁱ	0.91	2.55	3.336 (3)	145

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help with this work.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wadher, S. J., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). Int. J. PharmTech Res. 1, 22–33. CAS Google Scholar

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